(19)
(11)EP 3 263 569 B1

(12)EUROPEAN PATENT SPECIFICATION

(45)Mention of the grant of the patent:
27.11.2019 Bulletin 2019/48

(21)Application number: 17177730.3

(22)Date of filing:  23.06.2017
(51)Int. Cl.: 
C07D 405/10  (2006.01)
H01L 51/50  (2006.01)
C07D 209/82  (2006.01)
C09K 11/00  (2006.01)

(54)

CONDENSED CYCLIC COMPOUND, COMPOSITION INCLUDING THE SAME, AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE CONDENSED CYCLIC COMPOUND

KONDENSIERTE CYCLISCHE VERBINDUNG, ZUSAMMENSETZUNG DAMIT, UND ORGANISCHE LICHTEMITTIERENDE VORRICHTUNG MIT KONDENSIERTER CYCLISCHER VERBINDUNG

COMPOSÉ CYCLIQUE CONDENSÉ, COMPOSITION LE COMPRENANT, ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE COMPRENANT CE COMPOSÉ CYCLIQUE CONDENSÉ


(84)Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

(30)Priority: 27.06.2016 KR 20160080236

(43)Date of publication of application:
03.01.2018 Bulletin 2018/01

(73)Proprietors:
  • Samsung Electronics Co., Ltd.
    Gyeonggi-do 16677 (KR)
  • Samsung SDI Co., Ltd.
    Gyeonggi-do (KR)

(72)Inventors:
  • JUNG, Yongsik
    16678 Gyeonggi-do (KR)
  • HUH, Dalho
    16678 Gyeonggi-do (KR)
  • SON, Jhunmo
    16678 Gyeonggi-do (KR)
  • KWON, Eunsuk
    16678 Gyeonggi-do (KR)
  • KIM, Sangmo
    16678 Gyeonggi-do (KR)
  • LEE, Saeyoun
    16678 Gyeonggi-do (KR)
  • JEON, Soonok
    16678 Gyeonggi-do (KR)
  • CHUNG, Yeonsook
    16678 Gyeonggi-do (KR)
  • KIM, Jongsoo
    16678 Gyeonggi-do (KR)
  • IHN, Sooghang
    16678 Gyeonggi-do (KR)

(74)Representative: Elkington and Fife LLP 
Prospect House 8 Pembroke Road
Sevenoaks, Kent TN13 1XR
Sevenoaks, Kent TN13 1XR (GB)


(56)References cited: : 
EP-A1- 2 966 146
EP-A1- 3 113 239
WO-A1-2017/005699
EP-A1- 3 109 247
EP-A1- 3 190 164
CN-A- 105 418 486
  
  • MING-SHIANG LIN ET AL: "Incorporation of a CN group into mCP: a new bipolar host material for highly efficient blue and white electrophosphorescent devices", JOURNAL OF MATERIALS CHEMISTRY, vol. 22, no. 31, 1 January 2012 (2012-01-01), page 16114, XP055224872, GB ISSN: 0959-9428, DOI: 10.1039/c2jm32717a
  
Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).


Description

FIELD OF THE INVENTION



[0001] The present disclosure relates to a condensed cyclic compound, a composition including the same, and an organic light-emitting device including the condensed cyclic compound.

BACKGROUND OF THE INVENTION



[0002] Organic light-emitting devices (OLEDs) are self-emission devices that have wide viewing angles, high contrast ratios, and short response times. In addition, OLEDs display excellent brightness, driving voltage, and response speed characteristics, and produce full-color images.

[0003] In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons are changed from an excited state to a ground state, thereby generating light.

[0004] Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.

[0005] CN 105 418 486 discloses an organic electroluminescent compound, its use in organic photoelectric devices and an organic photoelectric device containing the same.

SUMMARY OF THE INVENTION



[0006] Provided are a novel condensed cyclic compound, a composition including the same, and an organic light-emitting device including the condensed cyclic compound.

[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

[0008] According to an aspect of an embodiment, a condensed cyclic compound is represented Formula 1B or 1C:



wherein, in Formulae 1B, 1C, and 2A,
A1 is a group represented by Formula 2A,
A11 is a single bond or *-C(R27)(R28)-*',
R1, and R2 are each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C1-C60 alkyl group, and a C1-C60 alkoxy group; and

a C1-C60 alkyl group and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and a cyano group,

a1 and a2 are each independently an integer selected from 0 to 4, wherein the sum a1 and a2 is 1 or more,

1, 2, 3, or 4 groups selected from R1 in the number of a1 and R2 in the number of a2 are a cyano group,

R11, R12, R21, R22, and R27 to R28 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and-B(Q6)(Q7),

R13 is the same as defined in connection with R11,

R14 is the same as defined in connection with R12,

a21 and a22 are each independently an integer selected from 0 to 4,

* and *' each indicate a binding site to a neighboring atom in a corresponding formula,

the total number of cyano groups in the condensed cyclic compound represented by Formulae 1B and 1C is 2, 3, or 4,

at least one substituent selected from substituent(s) of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C2-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

deuterium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;

a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium,-CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q11)(Q12)(Q13), -N(Q14)(Q15), and -B(Q16)(Q17);

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium,-CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q21)(Q22)(Q23), -N(Q24)(Q25), and -B(Q26)(Q27); and

-Si(Q31)(Q32)(Q33), -N(Q34)(Q35), and -B(Q36)(Q37), wherein

Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one of a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.



[0009] According to an aspect of another embodiment, a composition includes:

a first compound and a second compound,

wherein the first compound is the condensed cyclic compound represented by Formula 1B or 1C, and

wherein the second compound includes at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, an acridine-containing ring, a dihydroacridine-containing ring, and a triindolobenzene-containing ring and does not include an electron withdrawing group,

wherein the electron withdrawing group is selected from:

-F, -CFH2, -CF2H, -CF3, -CN, and -NO2;

a C1-C60 alkyl group substituted with at least one selected from -F, -CFH2,-CF2H, -CF3, -CN, and -NO2;

a C1-C60 heteroaryl group and a divalent non-aromatic condensed polycyclic heterocyclic group that each includes *=N-*' as a ring-forming moiety; and

a C1-C60 heteroaryl group and a divalent non-aromatic condensed polycyclic heterocyclic group that are each substituted with at least one selected from deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group and that each includes *=N-*' as a ring-forming moiety.



[0010] According to an aspect of another embodiment, a thin film includes the aforementioned composition.

[0011] According to an aspect of another embodiment, an organic light-emitting device includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer including an emission layer, and

wherein the organic layer includes at least one condensed cyclic compound represented by Formula 1B or 1C.


BRIEF DESCRIPTION OF THE DRAWINGS



[0012] These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with FIG. 1, which is a schematic cross-sectional view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION OF THE EMBODIMENTS



[0013] Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of," when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0014] It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

[0015] It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.

[0016] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting.

[0017] The term "or" means "and/or." It will be further understood that the terms "comprises" and/or "comprising," or "includes" and/or "including" when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

[0018] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0019] Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

[0020] "About" or "approximately" as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ± 30%, 20%, 10%, 5% of the stated value.

[0021] According to an aspect of the present inventive concept, a condensed cyclic compound is represented by Formula 1B or 1C:



[0022] In Formula 1B and 1C, A1 is a group represented by Formula 2A:



[0023] Formulae 2A is defined herein in the present specification.

[0024] In Formulae 2A, A11 is a single bond or *-C(R27)(R28)-*', * and *' each indicate a binding site to a neighboring atom, and R27 to R28 are each independently as defined herein in the present specification.

[0025] In an embodiment, A11 in Formula 2A may be a single bond, but embodiments are not limited thereto.

[0026] In Formula 1B and 1C, R1 and R2 are each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C1-C60 alkyl group, and a C1-C60 alkoxy group; and

a C1-C60 alkyl group and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and a cyano group.



[0027] In various embodiments, in Formula 1B and 1C, R1 and R2 may each independently be selected from:

hydrogen, deuterium, -F, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group; and

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, and a cyano group, but embodiments are not limited thereto.



[0028] In Formula 1B and 1C, a1 and a2 each indicate the number of groups R1 and the number of groups R2, and a1 and a2 are each independently an integer selected from 0 to 4, wherein the sum of a1 and a2 may be 1 or more.

[0029] In an embodiment, in Formula 1B and 1C, a1 and a2 may each independently be 0, 1, or 2, wherein the sum of a1 and a2 may be 1, 2, or 3.

[0030] In various embodiments, in Formula 1B and 1C, a1 and a2 may each independently be 0 or 1, wherein the sum of a1 and a2 may be 1 or 2.

[0031] In Formula 1B and 1C, 1, 2, 3, or 4 groups selected from R1 in the number of a1 and R2 in the number of a2 are a cyano group.

[0032] In an embodiment, in Formula 1B and 1C, 1, 2, or 3 groups selected from R1 in the number of a1 and R2 in the number of a2 may be a cyano group.

[0033] In various embodiments, in Formula 1B and 1C,
  1. i) 1 or 2 among R1 in the number of a1 may be a cyano group, and R2 may be a cyano group;
  2. ii) 1 or 2 among R1 in the number of a1 may be a cyano group, and 1 or 2 among R2 in the number of a2 may be a cyano group; or
  3. iii) R1 may not be a cyano group, and 1 or 2 among R2 in the number of a2 may be a cyano group,
but embodiments are not limited thereto.

[0034] In Formulae 1B, 1C and 2A, R11, R12, R21, R22, and R27 to R28 are each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and -B(Q6)(Q7), wherein Q1 to Q7 are each independently as defined herein in the present specification.

[0035] In an embodiment, in Formulae 1, 2A, and 2B, R11, R12, R21, R22, and R27 to R28 may each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, and a pyridobenzothiazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, and a pyridobenzothiazinyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, -Si(Q31)(Q32)(Q33),-N(Q34)(Q35), and -B(Q36)(Q37); and

-Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and -B(Q6)(Q7), wherein

Q1 to Q7 and Q31 to Q37 may each independently be selected from hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.



[0036] In various embodiments, in Formulae 1B, 1C and 2A, R11, R12, R21, R22, and R27 to R28 may each independently be selected from:

hydrogen, deuterium, -F, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, a cyano group, -F, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a cyano group, -F, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and -Si(Q31)(Q32)(Q33); and

-Si(Q1)(Q2)(Q3), wherein

Q1 to Q3 and Q31 to Q33 may each independently be selected from hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.



[0037] In an embodiment, A1 in Formula 1B and 1C may be represented by Formulae 2A-1:



[0038] In Formulae 2A-1,
A11, R21, R22, and * are each independently as defined herein in the present specification,
R23 is the same as defined herein in connection with R21, and
R24 is the same as defined herein in connection with R22.

[0039] For example, in Formulae 2A-1, at least one of R23 and R24 may be a cyano group, but embodiments are not limited thereto.

[0040] In Formulae 1B and 1C, at least one of R13 and R14 may be a cyano group, but embodiments are not limited thereto.

[0041] In an embodiment, in Formulae 1B and 1C, A1 may be represented by Formulae 2A-1 and at least one selected from R13, R14, R23, and R24 (for example, 1 or 2 among R13, R14, R23, and R24) may be a cyano group; or

[0042] In various embodiments, A1 in Formula 1B and 1C may be identical to a first carbazole ring ("first carbazole ring" is the same as defined herein in connection with Formula 1') included in Formula 1B and 1C.

[0043] In various embodiments, A1 in Formula 1B and 1C may be different from a first carbazole ring ("first carbazole" is the same as defined herein in connection with Formula 1') included in Formula 1B or 1C.

[0044] In various embodiments, the condensed cyclic compound represented by Formula 1B or 1C may have a symmetrical structure.

[0045] In various embodiments, the condensed cyclic compound represented by Formula 1B or 1C may have an asymmetrical structure.

[0046] In various embodiments, the condensed cyclic compound may be represented by one selected from Formulae 1B-1 to 1B-76 and 1C-1 to 1C-76, but embodiments are not limited thereto:













































































[0047] In Formulae 1B-1 to 1B-76 and 1C-1 to 1C-76,
A1, R11, and R12 are each independently as defined herein in the present specification,
R8 to R10 and R10a are each independently the same as defined herein in connection with R1,
R3 to R7 are each independently the same as defined herein in connection with R2,
R13 is the same as defined herein in connection with R11, and
R14 is the same as defined herein in connection with R12.

[0048] For example, in Formulae 1B-1 to 1B-76 and 1C-1 to 1C-76, R3 to R10 and R10a may not be a cyano group.

[0049] In various embodiments, in Formulae 1B-1 to 1B-76 and 1C-1 to 1C-76, R3 to R10 and R10a may each independently be selected from:

hydrogen, deuterium, -F, a C1-C20 alkyl group, and a C1-C20 alkoxy group; and

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of deuterium and -F, but embodiments are not limited thereto.



[0050] For example, in Formulae 1B-1 to 1B-76 and 1C-1 to 1C-76, A1 may be selected from groups represented by Formulae 2B-1 to 2B-4, but embodiments are not limited thereto.

[0051] In various embodiments, in Formula 1B and 1C, R11, R12, R21, R22, and R27 to R28 may not be a substituted or unsubstituted carbazolyl group.

[0052] For example, the condensed cyclic compound may be selected from Compounds 54 to 100, 104 to 105, 112 to 153, 156 to 158, 291, 292, 295, 297, 298 and 300, but embodiments are not limited thereto. The remaining compounds shown below do not form part of the present invention:





































































































































[0053] In Formula 1B and 1C, a first carbazole ring is combined with a carbon atom at an "ortho-position" with respect to a carbon atom combined with a second benzene ring of a first benzene ring (see Formula 1'). In this regard, the condensed cyclic compound represented by Formula 1B and 1C may have a relatively high triplet state (T1) energy level, compared to a compound structure combined with a carbon atom at a "para-position" or a "meta-position". Accordingly, a material, such as a host material included in an emission layer, for forming an organic light-emitting device may have suitable electric characteristics to be applied to a blue light-emitting device. Therefore, an organic light-emitting device including the condensed cyclic compound may exhibit high efficiency and long lifespan.



[0054] In addition, in Formula 1B and 1C, 1, 2, 3, or 4 groups selected from R1 in the number of a1 and R2 in the number of a2 may be a cyano group. That is, in a biphenylene group of Formula 1B and 1C is substituted with 1 to 4 cyano group(s) (see Formula 1'). In addition, in Formula 1B and 1C, R1 and R2 are not a "cyclic group". Thus, the condensed cyclic compound may have a relatively low lowest unoccupied molecular orbital (LUMO) energy level (i.e., a relatively large absolute value of the LUMO energy level) and excellent electron mobility. Accordingly, a material, such as a host material included in an emission layer, for forming an organic light-emitting device may have suitable electric characteristics. Therefore, an organic light-emitting device including the condensed cyclic compound may exhibit high efficiency and long lifespan.

[0055] For example, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO), triplet state (T1) energy level, and singlet state (S1) energy level of Compounds 1, 3, 5, 7, 26, 46, 52, 55, 95, 97, 106, 176, 179, 216, and 219 and Compounds A and B evaluated through simulations using DFT methods of Gaussian programs (molecular structures are optimized at the B3LYP, 6-31 G(d,p) levels), and the evaluation results are shown in Table 1:
Table 1
Compound No.HOMO (eV)LUMO (eV)T1 (eV)S1 (eV)
1 -5.577 -1.604 3.164 3.285
3 -5.555 -1.750 3.134 3.212
5 -5.735 -1.880 3.132 3.237
7 -5.780 -2.096 2.987 3.033
26 -5.780 -1.859 3.119 3.355
46 -5.394 -1.722 3.034 3.128
52 -5.570 -1.642 3.098 3.331
55 -5.719 -1.956 3.021 3.109
95 -5.722 -1.887 3.118 3.256
97 -5.898 -2.052 3.058 3.161
106 -5.442 -1.730 3.035 3.172
176 -5.321 -1.564 3.037 3.166
179 -5.404 -1.329 2.992 3.483
216 -5.497 -1.632 3.062 3.164
219 -5.474 -1.444 3.068 3.439
A -5.799 -2.144 2.936 3.098
B -5.273 -1.090 3.166 3.644




[0056] Referring to Table 1, it was confirmed that the condensed cyclic compound represented by Formula 1B or 1C had a higher T1 energy level than that of Compound A, and a lower LUMO energy level than that of Compound B, wherein such a low LUMO energy level is advantageous for movement of electrons within an emission layer. That is, it was confirmed that the condensed cyclic compound represented by Formula 1B or 1C having a relatively high T1 energy level and a low LUMO energy level was suitable for use in an emission layer of an electronic device, such as an organic light-emitting device.

[0057] Synthesis methods of the condensed cyclic compound represented by Formula 1B or 1C may be understood by those of ordinary skill in the art by referring to Synthesis Examples that will described below.

[0058] According to another aspect of the present inventive concept, a composition includes a first compound and a second compound, wherein the first compound is the condensed cyclic compound represented by Formula 1B or 1C, and the second compound includes at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, an acridine-containing ring, a dihydroacridine-containing ring, and a triindolobenzene-containing ring, and does not include an electron withdrawing group,
wherein the electron withdrawing group is selected from:

-F, -CFH2, -CF2H, -CF3, -CN, and -NO2;

a C1-C60 alkyl group substituted with at least one selected from -F, -CFH2,-CF2H, -CF3, -CN, and -NO2;

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group that each includes *=N-*' as a ring-forming moiety; and

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group that are each substituted with at least one selected from deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group and that each includes *=N-*' as a ring-forming moiety.



[0059] The composition may be suitable for use in preparation of an organic layer of an electronic device (such as an organic light-emitting device).

[0060] In the composition, the first compound may be an electron transport material, and the second compound may be a hole transport material.

[0061] In an embodiment, the composition may consist of the first compound and the second compound, but embodiments are not limited thereto.

[0062] In the composition, the condensed cyclic compound that is represented by Formula 1B or 1C may be the first compound as defined herein in the present specification.

[0063] For example, the second compound in the composition may be selected from a compound represented by Formula H-1:

        Formula H-1     Ar1-(L1)c1-Ar2





[0064] In Formulae H-1, 11, and 12,
L1 may be selected from:

a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and -Si(Q11)(Q12)(Q13),

c1 may be an integer selected from 1 to 10, wherein, when c1 is 2 or more, 2 or more L1 may be identical to or different from each other,

Ar1 may be selected from groups represented by Formulae 11 and 12,

Ar2 may be selected from:

groups represented by Formulae 11 and 12, a phenyl group, and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group,

CY1 and CY2 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, and a dibenzothiophene group,

A21 may be selected from:

a single bond, a C1-C4 alkylene group, and a C2-C4 alkenylene group; and

a C1-C4 alkylene group and a C2-C4 alkenylene group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and-Si(Q21)(Q22)(Q23),

R30, R40, and R51 may each independently be selected from:

hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group; and

-Si(Q1)(Q2)(Q3),

b1 and b2 may each independently be an integer selected from 0 to 10,

Q1 to Q3, Q11 to Q13, and Q21 to Q23 may each independently be selected from hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group, and

* indicates a binding site to a neighboring atom.



[0065] For example, in Formula H-1, c1 indicates the number of groups L1, and may be 1, 2, 3, or 4.

[0066] In various embodiments, in Formulae 11 and 12, at least one of CY1 and CY2 may be a benzene group, but embodiments are not limited thereto.

[0067] In an embodiment, in Formula H-1,
Ar1 may be selected from groups represented by Formulae 11-1 to 11-8 and 12-1 to 12-16, and
Ar2 may be selected from:

groups represented by Formulae 11-1 to 11-8 and 12-1 to 12-16, a phenyl group, and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group, but embodiments are not limited thereto:

























[0068] In Formulae 11-1 to 11-8 and 12-1 to 12-16,
X11 and X13 may each independently be C(R37)(R38), N(R39), O, or S,
A21, R51, and * are each independently as defined herein in the present specification,
R31 to R39 are each independently the same as defined herein in connection with R30, and
R41 to R44 are each independently the same as defined herein in connection with R40.

[0069] In various embodiments, in Formulae 11 and 12, A21 may be selected from:

a single bond, a C1-C2 alkylene group, and a C2 alkenylene group; and

a C1-C2 alkylene group and a C2 alkenylene group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and-Si(Q21)(Q22)(Q23), but embodiments are not limited thereto. Here, Q21 to Q23 are each independently the same as defined herein in the present specification.



[0070] In various embodiments, in the composition,
  1. i) the second compound may be selected from compounds represented by Formula H-1, wherein L1 in Formula H-1 may be a single bond; or
  2. ii) the second compound may be selected from compounds represented by Formulae H-1 (1) to H-1 (52), but embodiments are not limited thereto:



































[0071] In Formulae H-1 (1) to H-1 (52),
Ar1 and Ar2 are each independently as defined herein in the present specification,
Y51 may be C(Z53)(Z54), N(Z55), O, or S,
Z51 to Z56 may each independently be selected from hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and -Si(Q11)(Q12)(Q13), wherein
Q11 to Q13 may each independently be selected from hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, and a naphthyl group, but embodiments are not limited thereto.

[0072] In the composition, the second compound may be selected from Compounds H-1 to H-32, but embodiments are not limited thereto:















[0073] In the composition, a weight ratio of the first compound and the second compound may be selected from ranges of 1:99 to 99:1, for example, ranges of 70:30 to 30:70. For example, in the composition, the weight ratio of the first compound and the second compound may be selected from ranges of 40:60 to 60:40, but embodiments are not limited thereto. While not wishing to be bound by theory, it is understood that when the weight ratio of the first compound and the second compound in the composition is within any of these ranges, the composition may provide excellent charge transport balance.

[0074] The condensed cyclic compound represented by Formula 1B or 1C may be suitable for use in an organic layer of an organic light-emitting device, for example, in an emission layer and/or an electron transport region of the organic layer.

[0075] According to another aspect of the present inventive concept, an organic light-emitting device includes:

a first electrode,

a second electrode, and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer includes an emission layer, and

wherein the organic layer includes at least one condensed cyclic compound represented by Formula 1B or 1C.



[0076] The organic light-emitting device including the organic layer including the condensed cyclic compound represented by Formula 1B or 1C may exhibit low driving voltage, high emission efficiency, high luminance, high quantum emission efficiency, and long lifespan.

[0077] In an embodiment, in the organic light-emitting device,
the first electrode may be an anode,
the second electrode may be a cathode,
the organic layer may include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region may include at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and
wherein the electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer, but embodiments are not limited thereto.

[0078] For example, the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C.

[0079] In various embodiments, the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C, which may be used as a delayed fluorescence material.

[0080] In an embodiment, the emission layer may include a host and a dopant (wherein an amount of the host may be greater than that of the dopant), and the host may include the condensed cyclic compound represented by Formula 1B or 1C. The condensed cyclic compound, which serves as the host, may deliver energy to a dopant according to the delayed fluorescence mechanism. Here, the dopant may include at least one of a fluorescent dopant and a phosphorescent dopant. The dopant may be selected from known dopants in the art. The host may further include, in addition to the condensed cyclic compound represented by Formula 1B or 1C, a host selected from known hosts in the art.

[0081] In various embodiments, the emission layer may include a host and a dopant (wherein an amount of the host may be greater than that of the dopant), and the dopant may include the condensed cyclic compound represented by Formula 1B or 1C. The condensed cyclic compound, which serves as the dopant, may emit delayed fluorescence according to the delayed fluorescence mechanism. Here, the host may further include, in addition to the condensed cyclic compound represented by Formula 1B or 1C, a dopant selected from known dopants in the art.

[0082] The emission layer may emit red light, green light, or blue light.

[0083] In an embodiment, the emission layer may be a blue emission layer including a phosphorescent dopant, but embodiments are not limited thereto.

[0084] In various embodiments, the emission layer may include a host and a dopant, wherein the host may include the condensed cyclic compound represented by Formula 1B or 1C and the dopant may include a phosphorescent dopant.

[0085] In various embodiments, the electron transport region may include the condensed cyclic compound represented by Formula 1B or 1C.

[0086] For example, the electron transport region of the organic light-emitting device may include at least one of a hole blocking layer and an electron transport layer, wherein the at least one of the electron blocking layer and the electron transport layer may include the condensed cyclic compound represented by Formula 1B or 1C.

[0087] In an embodiment, the electron transport region of the organic light-emitting device may include a hole blocking layer, wherein the hole blocking layer may include the condensed cyclic compound represented by Formula 1B or 1C. Here, the hole blocking layer may directly contact the emission layer.

[0088] In various embodiments, the organic layer of the organic light-emitting device may further include, in addition to the condensed cyclic compound represented by Formula 1B or 1C,
  1. i) the second compound;
  2. ii) an organometallic compound represented by Formula 81; or
  3. iii) any combination of i) and ii):

            Formula 81     M(L81)n81(L82)n82





[0089] In Formulae 81 and 81A,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh),

L81 may be a ligand represented by Formula 81A, and n81 may be an integer selected from 1 to 3, wherein, when n81 is 2 or more, 2 or more L81 may be identical to or different from each other,

L82 may be an organic ligand, and n82 may be an integer selected from 0 to 4, wherein, when n82 is 2 or more, 2 or more L82 may be identical to or different from each other,

Y81 to Y84 may each independently be C or N,

Y81 and Y82 may be linked via a single bond or a double bond, and Y83 and Y84 may be linked via a single bond or a double bond,

CY81 and CY82 may each independently be selected from a C5-C30 carbocyclic group and a C3-C30 heterocarbocyclic group,

CY81 and CY82 may be optionally further linked via an organic linking group,

R81 to R85 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q81)(Q82)(Q83), -N(Q84)(Q85), -B(Q86)(Q87), and -P(=O)(Q88)(Q89),

a81 to a83 may each independently be an integer selected from 0 to 5,

wherein, when a81 is 2 or more, 2 or more R81 may be identical to or different from each other,

when a82 is 2 or more, 2 or more R82 may be identical to or different from each other,

when a81 is 2 or more, two adjacent R81 may be optionally linked to form a saturated or unsaturated C2-C30 ring (for example, a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a (bicyclo[2.2.1]heptanes) ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or a saturated or unsaturated C2-C30 ring substituted with at least one R88 (for example, a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a (bicyclo[2.2.1]heptanes) ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring, each substituted with at least one R88),

when a82 is 2 or more, two adjacent R82 may be optionally linked to form a saturated or unsaturated C2-C30 ring (for example, a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a (bicyclo[2.2.1]heptanes) ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or a saturated or unsaturated C2-C3 ring substituted with at least one R89 (for example, a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a (bicyclo[2.2.1]heptanes) ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring, each substituted with at least one R89),

R88 is the same as defined herein in connection with R81,

R89 is the same as defined herein in connection with R82,

* and *' in Formula 81A each indicate a binding site to M of Formula 81,

at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and -Si(Q91)(Q92)(Q93), and

Q81 to Q89 and Q91 to Q93 may each independently be selected from hydrogen, deuterium, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.



[0090] In an embodiment, in Formula 81A,
a83 may be 1 or 2,
R83 to R85 may each independently be selected from:

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2,-CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group, but embodiments are not limited thereto.



[0091] In various embodiments, in Formula 81A,
Y81 may be N, Y82 and Y83 may each independently be C, and Y84 may be N or C,
CY81 and CY82 may each independently be selected from a cyclopentadiene group, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corozene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, an indazole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthrididine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a benzocarbazole group, a dibenzocarbazole group, an imidazopyridine group, an imidazopyrimidine group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilol group, and a 2,3-dihydro-1H-imidazole group.

[0092] In various embodiments, in Formula 81A, Y81 may be N, Y82 to Y84 may each independently be C, CY81 may be selected from 5-membered ring including two nitrogen atoms as ring-forming atoms, and CY82 may be selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group, but embodiments are not limited thereto.

[0093] In various embodiments, in Formula 81A, Y81 may be N, Y82 to Y84 may each independently be C, CY81 may be an imidazole group or a 2,3-dihydro-1H-imidazole group, and CY82 may be selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group, but embodiments are not limited thereto.

[0094] In various embodiments, in Formula 81A,
Y81 may be N,
Y82 to Y84 may each independently be C,
CY81 may be selected from a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, and an isobenzoxazole group, and
CY82 may be selected from a cyclopentadiene group, a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, and a dibenzosilol group.

[0095] In various embodiments, in Formula 81A,
R81 and R82 may each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H,-CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group (adamantyl), a norbornanyl group (norbornyl), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, - CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-B(Q86)(Q87) and -P(=O)(Q88)(Q89), wherein

Q86 to Q89 may each independently be selected from

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2,-CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group and a phenyl group.



[0096] In various embodiments, in Formula 81A, R81 and R82 may each independently be selected from:

hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, each substituted with at least one selected from deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a cyano group, a nitro group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; and

-B(Q86)(Q87) and -P(=O)(Q88)(Q89), wherein

Q86 to Q89 may each independently be selected from:

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2,-CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group.



[0097] In various embodiments, in Formula 81A, R81 and R82 may each independently be selected from hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groups represented by Formulae 9-1 to 9-19, and groups represented by Formulae 10-1 to 10-30, but embodiments are not limited thereto:



















[0098] In Formulae 9-1 to 9-17 and 10-1 to 10-30, * indicates a binding site to a neighboring atom.

[0099] In various embodiments, in Formula 81A, at least one selected from R81 in the number of a81 and R82 in the number of a82 may be a cyano group.

[0100] In various embodiments, in Formula 81A, at least one selected from R82 in the number of a82 may be a cyano group.

[0101] In various embodiments, in Formula 81A, at least one selected from R81 in the number of a81 and R82 in the number of a82 may be deuterium.

[0102] In various embodiments, in Formula 81, L82 may be selected from ligands represented by Formulae 3-1(1) to 3-1(60), 3-1(61) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114):

















































[0103] In Formulae 3-1(1) to 3-1(60), 3-1(61) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114),
X1 may be O, S, C(Z21)(Z22), or N(Z23),
X31 may be N or C(Z1a),
X32 may be N or C(Z1b),
X41 may be O, S, N(Z1a), or C(Z1a)(Z1b),
Z1 to Z4, Z1a, Z1b, Z1c, Z1d, Z2a, Z2b, Z2c, Z2d, Z11 to Z14, and Z21 to Z23 may each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H,-CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3,-CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-B(Q86)(Q87) and -P(=O)(Q88)(Q89), wherein

Q86 to Q89 may each independently be selected from:

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2,-CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group,

d2 and e2 may each independently be 0 or 2,

e3 may be an integer selected from 0 to 3,

d4 and e4 may each independently an integer selected from 0 to 4,

d6 and e6 may each independently an integer selected from 0 to 6,

d8 and e8 may each independently an integer selected from 0 to 8, and

* and *' each indicate a binding site to M of Formula 1B or 1C.



[0104] For example, Z1 to Z4, Z1a, Z1b, Z1c, Z1d, Z2a, Z2b, Z2c, Z2d, Z11 to Z14, and Z21 to Z23 may each independently be selected from hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groups represented by Formulae 9-1 to 9-19, and groups represented by Formulae 10-1 to 10-30, but embodiments are not limited thereto.

[0105] In various embodiments, in Formula 81, M may be Ir and the sum of n81 + n82 may be 3; or

[0106] M may be Pt and the sum of n81 + n82 may be 2.

[0107] In various embodiments, the organometallic compound represented by Formula 81 may neutral, rather than being a salt consisting of a pair of a cation and an anion.

[0108] In various embodiments, the organometallic compound represented by Formula 81 may include at least one selected from Compounds PD1 to PD78 and FIr6, but embodiments are not limited thereto:




















































FIr6



[0109] In an embodiment,
  1. i) the organic light-emitting device may further include the organometallic compound represented by Formula 81, and the emission layer of the organic light-emitting device may include a host and a dopant, wherein the host may include the condensed cyclic compound represented by Formula 1B or 1C (for example, the host may consist of the condensed cyclic compound represented by Formula 1B or 1C) and the dopant may include the organometallic compound represented by Formula 81;
  2. ii) the organic light-emitting device may further include the second compound (for example, the compound represented by Formula H-1), and the emission layer of the organic light-emitting device may include a host and a dopant, wherein the host may include the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1); or
  3. iii) the organic light-emitting device may further include the second compound (for example, the compound represented by Formula H-1) and the organometallic compound represented by Formula 81, the emission layer of the organic light-emitting device may include a host and a dopant, wherein the host may include the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1), and the dopant may include the organometallic compound represented by Formula 81.


[0110] The expression that "(an organic layer) includes at least one condensed cyclic compound" as used herein may include a case in which "(an organic layer) includes at least one condensed cyclic compound identical to the condensed cyclic compound represented by Formula 1" or a case in which (an organic layer) includes two or more condensed cyclic compounds different from the condensed cyclic compound represented by Formula 1".

[0111] For example, the organic layer may include, as the condensed cyclic compound, only Compound 1. Here, Compound 1 may be in the emission layer of the organic light-emitting device. In various embodiments, the organic layer may include, as the condensed cyclic compound, Compound 1 and Compound 2. Here, Compound 1 and Compound 2 may be in an identical layer (for example, Compound 1 and Compound 2 may both be in the emission layer), or in different layers (for example, Compound 1 may be in the emission layer and Compound 2 may be in the electron blocking layer).

[0112] The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode. In various embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

[0113] The term "organic layer" as used herein may refer to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device. The "organic layer" may include not only an organic compound, but also a metal-containing organometallic complex.

[0114] FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device, according to an embodiment, will be described in connection with FIG. 1. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in this stated order.

[0115] A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water-resistance.

[0116] The first electrode 11 may be, for example, formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In various embodiments, metals, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag), may be used as the material for forming the first electrode 11.

[0117] The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.

[0118] The organic layer 15 may be disposed on the first electrode 11.

[0119] The organic layer 15 may include a hole transport region, an emission layer; and an electron transport region.

[0120] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0121] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0122] The hole transport region may include only either a hole injection layer or a hole transport layer. In various embodiments, the hole transport region may have a structure of hole injection layer/hole transport layer, a structure of hole injection layer/hole transport layer/electron blocking layer, or a structure of hole transport layer/electron blocking layer, wherein the layers of each structure are sequentially stacked from the first electrode 11 in the stated order.

[0123] When hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.

[0124] When the hole injection layer is formed using vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer to be deposited, and the structure and thermal characteristics of the hole injection layer to be formed. For example, the deposition conditions may include a deposition temperature of about 100°C to about 500°C, a vacuum pressure of about 10-8 torr to about 10-3 torr, and a deposition rate of about 0.001 nm/sec to about 10 nm/sec (about 0.01 Å/sec to about 100 Å/sec), but the deposition conditions are not limited thereto.

[0125] When the hole injection layer is formed using spin coating, the coating conditions may vary depending on a material that is used to form the hole injection layer to be deposited, and the structure and thermal characteristics of the hole injection layer to be formed. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80°C to about 200°C, but the coating conditions are not limited thereto.

[0126] Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.

[0127] The hole transport region may include, for example, at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:













[0128] In Formula 201, Ar101 and Ar102 may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.



[0129] In Formula 201, xa and xb may each independently be an integer selected from 0 to 5, or may each independently be 0, 1, or 2. For example, xa is 1, and xb may be 0, but embodiments are not limited thereto.

[0130] In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, or a hexyl group), and a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, pentoxy group);

a C1-C10 alkyl group and a C1-C10 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from deuterium, -F, - Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, and a C1-C10 alkoxy group, but embodiments are not limited thereto.



[0131] In Formula 201, R109 may be selected from:

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.



[0132] In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:



[0133] In Formula 201A, R101, R111, R112, and R109 are each independently the same as defined herein.

[0134] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may each be selected from Compounds HT1 to HT20, but embodiments are not limited thereto:















[0135] A thickness of the hole transport region may be in a range of about 10 nm to aobut 1,00 nm (about 100 Å to about 10,000 Å), for example, about 10 nm to about 100 nm (about 100 Å to about 1,000 Å). When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 10 nm to about 1,000 nm (about 100 Å to about 10,000 Å), for example, about 10 nm to about 100 nm (about 100 Å to about 1,000 Å), and a thickness of the hole transport layer may be in a range of about 5 nm to about 200 nm (about 50 Å to about 2,000 Å), for example, about 10 nm to about 150 nm (about 100 Å to about 1,500 Å). While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

[0136] The hole transport region may further include, in addition to these materials, a charge-generation material for improving conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

[0137] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide and a molybdenum oxide; and a cyano group-containing compound, such as Compounds HT-D1 and HP-1, but embodiments are not limited thereto:





[0138] The hole transport region may further include a buffer layer.

[0139] The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, the efficiency of a formed organic light-emitting device may be improved.

[0140] The emission layer may be formed on the hole transport region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, and LB deposition. When the emission layer is formed using vacuum deposition and spin coating, the deposition and coating conditions for the emission layer may be similar with those for forming the hole injection layer, although deposition and coating conditions may vary according to a material that is used to form the emission layer.

[0141] The hole transport region may further include an electron blocking layer. The electron blocking layer may include a known compound, such as mCP, but embodiments are not limited thereto:



[0142] A thickness of the electron blocking layer may be in a range of about 5 nm to about 100 nm (about 50 Å to about 1,000 Å), for example, about 7 nm to about 50 nm (about 70 Å to about 500 Å). While not wishing to be bound by theory, it is understood that when the thickness of the electron blocking layer is within these ranges, satisfactory electron blocking characteristics may be obtained without a substantial increase in driving voltage.

[0143] When the organic light-emitting device 10 is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In various embodiments, the emission layer may have a stacked structure including a red emission layer, a green emission layer and/or a blue emission layer, thereby emitting light.

[0144] The emission layer may include the condensed cyclic compound represented by Formula 1B or 1C.

[0145] For example, the emission layer may only include the condensed cyclic compound represented by Formula 1B or 1C.

[0146] In various embodiments, the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C, and may further include:
  1. i) the second compound (for example, the compound represented by Formula H-1);
  2. ii) the organometallic compound represented by Formula 81; or
  3. iii) any combination of i) and ii).


[0147] The condensed cyclic compound represented by Formula 1B or 1C, the second compound, and the organometallic compound represented by Formula 81 are each independently the same as defined herein.

[0148] In an embodiment,
  1. i) the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C and the organometallic compound represented by Formula 81 wherein an amount of the condensed cyclic compound represented by Formula 1B or 1C is greater than that of the organometallic compound represented by Formula 81;
  2. ii) the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1), wherein the emission layer optionally includes a known dopant in the art; or
  3. iii) the emission layer may include the condensed cyclic compound represented by Formula 1B or 1C, the second compound (for example, the compound represented by Formula H-1), and the organometallic compound represented by Formula 81, wherein the total amounts of the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1) may be greater than the amount of the organometallic compound represented by Formula 81, but embodiments are not limited thereto.


[0149] In various embodiments, the emission layer may include a host and a dopant, wherein
  1. i) the host may include the condensed cyclic compound represented by Formula 1B or 1C, and the dopant may include the organometallic compound represented by Formula 81;
  2. ii) the host may include the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1), and a known dopant; or
  3. iii) the host may include the condensed cyclic compound represented by Formula 1B or 1C and the second compound (for example, the compound represented by Formula H-1), and the dopant may include the organometallic compound represented by Formula 81, but embodiments are not limited thereto.


[0150] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the emission layer, but embodiments are not limited thereto. While not wishing to be bound by theory, it is understood that when the amount of the dopant is within the range above, emission may be implemented without a quenching phenomenon.

[0151] In various embodiments, when the emission layer includes the condensed cyclic compound represented by Formula 1B or 1C and the second compound, weight ratios of the condensed cyclic compound represented by Formula 1B or 1C and the second compound may be selected from ranges of 1:99 to 99:1, for example, ranges of 70:30 to 30:70. In various embodiments, the weight ratios of the condensed cyclic compound represented by Formula 1B or 1C and the second compound may be selected from ranges of 60:40 to 40:60. While not wishing to be bound by theory, it is understood that when the weight ratio of the condensed cyclic compound represented by Formula 1B or 1C and the second compound in the emission layer is within any of these ranges, the charge transport balance may be efficiently achieved in the emission layer.

[0152] A thickness of the emission layer may be in a range of about 10 nm to about 100 nm (about 100 Å to about 1,000 Å), for example, about 20 nm to about 60 nm (about 200 Å to about 600 Å). While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within any of these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

[0153] Next, an electron transport region may be disposed on the emission layer.

[0154] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0155] For example, the electron transport region may have a structure of hole blocking layer/electron transport layer/electron injection layer or a structure of electron transport layer/electron injection layer, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more layers.

[0156] Conditions for forming a hole transport layer, an electron blocking layer, and an electron injection layer of the electron transport region may be understood by referring to conditions for forming the hole injection layer.

[0157] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but embodiments are not limited thereto:



[0158] In various embodiments, the hole blocking layer may include the condensed cyclic compound represented by Formula 1B or 1C.

[0159] A thickness of the hole blocking layer may be in a range of about 2 nm to about 100 nm (about 20 Å to about 1,000 Å), for example, about 3 nm to about 30 nm (about 30 Å to about 300 Å). While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

[0160] The electron transport layer may further include at least one selected from BCP, Bphen, Alq3, Balq, TAZ, and NTAZ:





[0161] In various embodiments, the electron transport layer may include at least one selected from Compounds ET1, ET2, and ET3, embodiments are not limited thereto:





[0162] A thickness of the electron transport layer may be in a range of about 10 nm to about 100 nm (about 100 Å to about 1,000 Å), for example, about 15 nm to about 50 nm (about 150 Å to about 500 Å). While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer within any of these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.

[0163] The electron transport layer may further include, in addition to these materials, a metal-containing material.

[0164] The metal-containing material may include a lithium (Li) complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate (LiQ)) or Compound ET-D2:



[0165] In addition, the electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.

[0166] The electron injection layer may include at least one selected from LiQ, LiF, NaCl, CsF, Li2O, and BaO.

[0167] A thickness of the electron injection layer may be in a range of about 0.1 nm to about 10 nm (about 1 Å to about 100 Å), for example, about 0.3 nm to about 9 nm (about 3 Å to about 90 Å). While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within any of these ranges, satisfactory electron injecting characteristics may be obtained without a substantial increase in driving voltage.

[0168] The second electrode 19 may be disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal having a relatively low work function, an alloy, an electrically conductive compound, and a combination thereof. For example, Li, Mg, Al, Al-Li, Ca, Mg-In, or Mg-Ag may be used as a material for forming the second electrode 19. In various embodiments, to manufacture a top emission-type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0169] Hereinbefore, the organic light-emitting device 10 has been described with reference to FIG. 1, but is not limited thereto.

[0170] A C1-C60 alkyl group as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. A C1-C60 alkylene group as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.

[0171] A C1-C60 alkoxy group as used herein refers to a monovalent group represented by -OA101 (wherein A101 is the C1-C60 alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy (iso-propoxy) group.

[0172] A C2-C60 alkenyl group as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon double bond in the middle or at either terminal end of the C2-C60 alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group. A C2-C60 alkenylene group as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.

[0173] A C2-C60 alkynyl group as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon triple bond in the middle or at either terminal end of the C2-C60 alkyl group. Examples thereof include an ethynyl group and a propynyl group. A C2-C60 alkynylene group as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.

[0174] A C3-C10 cycloalkyl group as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C3-C10 cycloalkylene group as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.

[0175] A C1-C10 heterocycloalkyl group as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. A C1-C10 heterocycloalkylene group as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.

[0176] A C3-C10 cycloalkenyl group as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof, and which is not aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. A C3-C10 cycloalkenylene group as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.

[0177] A C1-C10 heterocycloalkenyl group as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the ring. Examples of the C2-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. A C1-C10 heterocycloalkenylene group as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.

[0178] A C6-C60 aryl group as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C6-C60 arylene group as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each includes two or more rings, the respective rings may be fused to each other.

[0179] A C1-C60 heteroaryl group as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and 1 to 60 carbon atoms. A C1-C60 heteroarylene group as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, and S as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each includes two or more rings, the respective rings may be fused with each other.

[0180] A C6-C60 aryloxy group as used herein indicates -OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group as used herein indicates -SA103 (wherein A103 is the C6-C60 aryl group).

[0181] A monovalent non-aromatic condensed polycyclic group as used herein refers to a monovalent group (for example, a group having 8 to 60 carbon atoms) that has two or more rings condensed to each other, only carbon atoms as a ring forming atom, and which is non-aromatic in the entire molecular structure. An example of the non-aromatic condensed polycyclic group includes a fluorenyl group. A divalent non-aromatic condensed polycyclic group as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0182] A monovalent non-aromatic condensed heteropolycyclic group as used herein refers to a monovalent group (for example, a group having 1 to 60 carbon atoms) that has two or more rings condensed to each other, has a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and which is non-aromatic in the entire molecular structure. An example of the monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group. A divalent non-aromatic condensed heteropolycyclic group as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0183] In Formula 1B and 1C, at least one of substituents selected from the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

deuterium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;

a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium,-CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q11)(Q12)(Q13),-N(Q14)(Q15), and -B(Q16)(Q17);

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium,-CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q21)(Q22)(Q23),-N(Q24)(Q25), and -B(Q26)(Q27); and

-Si(Q31)(Q32)(Q33), -N(Q34)(Q35), and -B(Q36)(Q37), wherein

Q11 to Q17, Q21 to Q27, and Q31 to Q37 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one of a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.



[0184] When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting "substituted" group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group and the carbon atoms (if any) contained in the substituent. For example, when the term "substituted C1-C30 alkyl" refers to a C1-C30 alkyl group substituted with C6-C30 aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C7-C60.

[0185] The term "biphenyl group" as used herein refers to a monovalent group in which two benzene groups are linked via a single bond.

[0186] The term "terphenyl group" as used herein refers to a monovalent group in which three benzene groups are linked via a single bond.

[0187] Unless stated otherwise in the present specification, * and *' each indicate a binding site to a neighboring atom in a formula.

[0188] Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples below, but the present inventive concept is not limited thereto. The expression "'B' was used instead of 'A"' used in describing Synthesis Examples below means that the number of molar equivalents of 'B' used was identical to the number of molar equivalents of 'A'.

EXAMPLES


Synthesis Example 1: Synthesis of Compound 1



[0189] Compound 1 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (A)



[0190] 15.0 grams (g) (89.7 millimoles, mmol) of carbazole was dissolved in 200 milliliters (ml) of dimethylformamide (DMF), and the mixed solution was cooled to a temperature of 0°C. 3.77 g (94.19 mmol) of sodium hydride (NaH, 60 % dispersion in mineral oil) was slowly added thereto, the resulting mixed solution was stirred at a temperature of 0°C for 30 minutes, and a solution in which 19.7 g (98.7 mmol) of 3-bromo-2-fluorobenzonitrile was dissolved in 50 ml of DMF was slowly added thereto for 10 minutes. Meanwhile, the reaction temperature was raised to 150°C, and an additional stirring process was performed on the reaction solution for 18 hours. After completion, the resulting reaction solution was cooled to room temperature, and saturated ammonium chloride (NH4Cl) was added thereto to extract and separate an organic layer using dichloromethane (DCM). The obtained organic layer was dried with anhydrous magnesium sulfate (MgSO4) to remove water therefrom, filtered, and concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing the desired compound, 24.3 g (yield: 78%) of Intermediate (A).
LC-Mass (calcd : 346.01 g/mol, found: M+1 = 347 g/mol)

Synthesis of Intermediate (B)



[0191] 20.0 g (57.6 mmol) of Intermediate (A), 9.67 g (69.1 mmol) of (2-fluorophenyl)boronic acid, 3.33 g (2.88 mmol) of tetrakistriphenylphosphine palladium (0) (Pd(PPh3)4), and 19.9 g (144 mmol) of potassium carbonate were added to a solution of 130 ml of TFT and 65 ml of water and mixed. The resulting mixed solution was stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained aqueous solution layer was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 15.0 g (yield: 72%) of the desired compound, Intermediate (B).
LC-Mass (cald: 362.12 g/mol, found: M+1 = 363 g/mol)

Synthesis of Compound 1



[0192] 9.60 g (yield: 63%) of the desired compound, Compound 1, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 11.9 g (32.9 mmol) of Intermediate (B) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 509.19 g/mol, found: M+1 = 510 g/mol)

Synthesis Example 2: Synthesis of Compound 3



[0193] Compound 3 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (C)



[0194] 23.4 g (yield: 75%) of the desired compound, Intermediate (C), was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 19.7 g (98.7 mmol) of 3-bromo-4-fluorobenzonitrile was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 346.01 g/mol, found: M+1 = 347 g/mol)

Synthesis of Intermediate (D)



[0195] 14.4 g (yield: 69%) of the desired compound, Intermediate (D), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 20.0 g (57.6 mmol) of Intermediate (C) was used instead of Intermediate (A).
LC-Mass (cald: 362.12 g/mol, found: M+1 = 363 g/mol)

Synthesis of Compound 3



[0196] 8.23 g (yield: 54%) of the desired compound, Compound 3, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 11.9 g (32.9 mmol) of Intermediate (D) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 509.19 g/mol, found: M+1 = 510 g/mol)

Synthesis Example 3: Synthesis of Compound 5



[0197] Compound 5 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (E)



[0198] 15.0 g (75.0 mmol) of 3-bromo-2-fluorobenzonitrile, 22.9 g (90.0 mmol) of bis(pinacolato)diboron, 3.06 g (3.75 mmol) of PdCl2(dppf)•CH2Cl2, and 22.1 g (225 mmol) of potassium acetate were dissolved in 250 ml of DMF, and the resulting solution was stirred at a temperature of 100°C for 24 hours. After completion of the reaction, the resulting reaction solution was cooled to room temperature and filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 12.4 g (yield: 67%) of the desired compound, Intermediate (E).
LC-Mass (cald: 247.12 g/mol, found: M+1 = 248 g/mol)

Synthesis of Intermediate (F)



[0199] 6.83 g (yield: 51%) of the desired compound, Intermediate (F), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 10.3 g (41.5 mmol) of Intermediate (E) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 387.12 g/mol, found: M+1 = 388 g/mol)

Synthesis of Compound 5



[0200] 5.37 g (yield: 84%) of the desired compound, Compound 5, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 5.10 g (13.2 mmol) of Intermediate (F) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 4: Synthesis of Compound 7



[0201] Compound 7 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (G)



[0202] 10.5 g (yield: 57%) of the desired compound, Intermediate (G), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 15.0 g (75.0 mmol) of 3-bromo-4-fluorobenzonitrile was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 247.12 g/mol, found: M+1 = 248 g/mol)

Synthesis of Intermediate (H)



[0203] 8.30 g (yield: 62%) of the desired compound, Intermediate (H), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 10.3 g (41.5 mmol) of Intermediate (G) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 387.12 g/mol, found: M+1 = 388 g/mol)

Synthesis of Compound 7



[0204] 7.19 g (yield: 75%) of the desired compound, Compound 7, was obtained in the same manner as in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 7.65 g (19.7 mmol) of Intermediate (H) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 5: Synthesis of Compound 26



[0205] Compound 26 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (I)



[0206] 17.8 g (yield: 46%) of the desired compound, Intermediate (I), was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 20.0 g (104 mmol) of 9H-carbazole-3-carbonitrile was used instead of carbazole.
LC-Mass (cald: 371.01 g/mol, found: M+1 = 372 g/mol)

Synthesis of Intermediate (J)



[0207] 11.9 g (yield: 67%) of the desired compound, Intermediate (J), was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 17.0 g (45.7 mmol) of Intermediate (I) was used instead of Intermediate (A).
LC-Mass (cald: 387.12 g/mol, found: M+1 = 388 g/mol)

Synthesis of Compound 26



[0208] 6.14 g (yield: 48%) of the desired compound, Compound 26, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 10.2 g (26.3 mmol) of Intermediate (J) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 6: Synthesis of Compound 46



[0209] Compound 46 was synthesized according to the reaction scheme shown below:



[0210] 12.2 g (yield: 83%) of the desired compound, Compound 46, was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 12.8 g (34.6 mmol) of 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 509.19 g/mol, found: M+1 = 510 g/mol)

Synthesis Example 7: Synthesis of Compound 52



[0211] Compound 52 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (K)



[0212] 14.7 g (yield: 80%) of the desired compound, Intermediate (G), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 15.0 g (75.0 mmol) of 3-bromo-5-fluorobenzonitrile was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 247.12 g/mol, found: M+1 = 248 g/mol)

Synthesis of Intermediate (L)



[0213] 8.60 g (yield: 51%) of the desired compound, Intermediate (L), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 15.0 g (46.6 mmol) of 9-(2-bromophenyl)-9H-carbazole was used instead of Intermediate (A) and 13.8 g (55.9 mmol) of Intermediate (G) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 362.12 g/mol, found: M+1 = 363 g/mol)

Synthesis of Compound 52



[0214] 6.86 g (yield: 75%) of the desired compound, Compound 52, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 7.15 g (19.7 mmol) of Intermediate (L) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 509.19 g/mol, found: M+1 = 510 g/mol)

Synthesis Example 8: Synthesis of Compound 55



[0215] Compound 55 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (M)



[0216] 7.20 g (yield: 43%) of the desired compound, Intermediate (M), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 12.8 g (51.8 mmol) of Intermediate (K) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 387.12 g/mol, found: M+1 = 388 g/mol)

Synthesis of Compound 55



[0217] 5.68 g (yield: 71%) of the desired compound, Compound 55, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 6.37 g (16.5 mmol) of Intermediate (M) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 9: Synthesis of Compound 95



[0218] Compound 95 was synthesized according to the reaction scheme shown below:



[0219] 5.28 g (yield: 38%) of the desired compound, Compound 95, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 5.00 g (26.0 mmol) of 9H-carbazole-3-carbonitrile was used instead of carbazole and 10.4 g (28.6 mmol) of Intermediate (L) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 10: Synthesis of Compound 97



[0220] Compound 97 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (N)



[0221] 8.56 g (yield: 82%) of the desired compound, Intermediate (N), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 4.84 g (34.6 mmol) of (3-fluorophenyl)boronic acid was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 362.12 g/mol, found: M+1 = 363 g/mol)

Synthesis of Compound 97



[0222] 3.19 g (yield: 31%) of the desired compound, Compound 97, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 4.00 g (18.4 mmol) of 9H-carbazole-3,6-dicarbonitrile was used instead of carbazole and 7.34 g (20.3 mmol) of Intermediate (N) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 559.18 g/mol, found: M+1 = 560 g/mol)

Synthesis Example 11: Synthesis of Compound 106



[0223] Compound 106 was synthesized according to the reaction scheme shown below:



[0224] 10.9 g (yield: 74%) of the desired compound, Compound 106, was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 12.8 g (34.6 mmol) of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 509.19 g/mol, found: M+1 = 510 g/mol)

Synthesis Example 12: Synthesis of Compound 176



[0225] Compound 176 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (O)



[0226] 15.0 g (52.2 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid, 19.2 g (67.9 mmol) of 1-bromo-3-iodobenzene, 3.02 g (2.61 mmol) of tetrakistriphenylphosphine palladium(0) (Pd(PPh3)4), and 18.1 g (131 mmol) of potassium carbonate were added to a solution of 120 ml of THF and 60 ml of water and mixed. The mixed solution was then stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained residue was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 17.2 g (yield: 74%) of the desired compound, Intermediate (O).
LC-Mass (cald: 445.03 g/mol, found: M+1 = 446 g/mol)

Synthesis of Intermediate (P)



[0227] 11.2 g (yield: 65%) of the desired compound, Intermediate (P), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 17.2 g (38.6 mmol) of Intermediate (O) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 445.36 g/mol, found: M+1 = 246 g/mol)

Synthesis of Intermediate (Q)



[0228] 5.99 g (yield: 65%) of the desired compound, Intermediate (Q), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 4.20 g (21.0 mmol) of 3-bromo-2-fluorobenzonitrile was used instead of Intermediate (A) and 11.2 g (25.2 mmol) of Intermediate (P) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 438.15 g/mol, found: M+1 = 439 g/mol)

Synthesis of Compound 176



[0229] 5.39 g (yield: 77%) of the desired compound, Compound 176, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 5.77 g (13.2 mmol) of Intermediate (Q) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 585.22 g/mol, found: M+1 = 586 g/mol)

Synthesis Example 13: Synthesis of Compound 179



[0230] Compound 179 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (R)



[0231] 15.0 g (52.2 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid, 27.3 g (104 mmol) of 3,5-dibromobenzonitrile, 3.02 g (2.61 mmol) of tetrakistriphenylphosphine palladium(O) (Pd(PPh3)4), and 18.1 g (131 mmol) of potassium carbonate were added to a solution of 120 ml of THF and 60 ml of water and mixed. The mixed solution was then stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained residue was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 11.9 g (yield: 54%) of the desired compound, Intermediate (R).
LC-Mass (cald: 422.04 g/mol, found: M+1 = 423 g/mol)

Synthesis of Intermediate (S)



[0232] 7.67 g (yield: 58%) of the desired compound, Intermediate (S), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 11.9 g (28.1 mmol) of Intermediate (R) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 470.22 g/mol, found: M+1 = 471 g/mol)

Synthesis of Compound 179



[0233] 6.49 g (yield: 83%) of the desired compound, Compound 179, was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 4.30 g (13.4 mmol) of 9-(2-bromophenyl)-9H-carbazole was used instead of Intermediate (A) and 7.53 g (16.0 mmol) of Intermediate (S) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 585.22 g/mol, found: M+1 = 586 g/mol)

Synthesis Example 14: Synthesis of Compound 216



[0234] Compound 216 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (T)



[0235] 13.0 g (yield: 85%) of the desired compound, Intermediate (T), was obtained in the same manner in which Intermediate (O) was synthesized according to Synthesis Example 12, except that 12.0 g (56.6 mmol) of dibenzo[b,d]furan-2-ylboronic acid was used instead of (9-phenyl-9H-carbazol-3-yl)boronic acid.
LC-Mass (cald: 369.99 g/mol, found: M+1 = 371 g/mol)

Synthesis of Intermediate (U)



[0236] 8.06 g (yield: 62%) of the desired compound, Intermediate (U), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 13.0 g (35.1 mmol) of Intermediate (T) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 370.17 g/mol, found: M+1 = 371 g/mol)

Synthesis of Intermediate (V)



[0237] 4.84 g (yield: 74%) of the desired compound, Intermediate (V), was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 3.60 g (18.0 mmol) of 3-bromo-2-fluorobenzonitrile was used instead of Intermediate (A) and 8.00 g (21.6 mmol) of Intermediate (U) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 363.11 g/mol, found: M+1 = 364 g/mol)

Synthesis of Compound 216



[0238] 4.89 g (yield: 80%) of the desired compound, Compound 216, was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 4.78 g (13.2 mmol) of Intermediate (V) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 510.17 g/mol, found: M+1 = 511 g/mol)

Synthesis Example 15: Synthesis of Compound 219



[0239] Compound 219 was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (W)



[0240] 15.2 g (yield: 77%) of the desired compound, Intermediate (W), was obtained in the same manner in which Intermediate (R) was synthesized according to Synthesis Example 13, except that 12.0 g (56.6 mmol) of dibenzo[b,d]furan-2-ylboronic acid was used instead of (9-phenyl-9H-carbazol-3-yl)boronic acid.
LC-Mass (cald: 346.99 g/mol, found: M+1 = 348 g/mol)

Synthesis of Intermediate (X)



[0241] 11.4 g (yield: 66%) of the desired compound, Intermediate (X), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 15.2 g (43.7 mmol) of Intermediate (W) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 395.17 g/mol, found: M+1 = 396 g/mol)

Synthesis of Compound 219



[0242] 5.99 g (yield: 54%) of the desired compound, Compound 219, was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 7.00 g (21.7 mmol) of 9-(2-bromophenyl)-9H-carbazole was used instead of Intermediate (A) and 10.3 g (26.1 mmol) of Intermediate (X) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 510.17 g/mol, found: M+1 = 511 g/mol)

Synthesis Example 16: Synthesis of Compound A



[0243] Compound A was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (Y)



[0244] 35.3 g (yield: 85%) of the desired compound, Intermediate (Y), was obtained in the same manner in which Intermediate (A) was synthesized according to Synthesis Example 1, except that 26.3 g (132 mmol) of 3-bromo-5-fluorobenzonitrile was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 346.01 g/mol, found: M+1 = 347 g/mol)

Synthesis of Intermediate (Z)



[0245] 15.7 g (yield: 69%) of the desired compound, Intermediate (Z), was obtained in the same manner in which Intermediate (E) was synthesized according to Synthesis Example 3, except that 20.0 g (57.6 mmol) of Intermediate (Y) was used instead of 3-bromo-2-fluorobenzonitrile.
LC-Mass (cald: 394.19 g/mol, found: M+1 = 395 g/mol)

Synthesis of Compound A



[0246] 15.4 g (yield: 91%) of the desired compound, Compound A, was obtained in the same manner in which Intermediate (B) was synthesized according to Synthesis Example 1, except that 11.0 g (31.7 mmol) of Intermediate (Y) was used instead of Intermediate (A) and 15.0 g (38.0 mmol) of Intermediate (Z) was used instead of (2-fluorophenyl)boronic acid.
LC-Mass (cald: 534.18 g/mol, found: M+1 = 535 g/mol)

Synthesis Example 17: Synthesis of Compound B



[0247] Compound B was synthesized according to the reaction scheme shown below:


Synthesis of Intermediate (AA)



[0248] 15.0 g (59.8 mmol) of 2,6-dibromoaniline, 53.0 g (143 mmol) of 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole, 6.91 g (5.98 mmol) of tetrakistriphenylphosphine palladium(0) (Pd(PPh3)4), and 41.3 g (299 mmol) of potassium carbonate were added to a solution of 260 ml of THF and 130 ml of water and mixed. The mixed solution was stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained residue was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 14.8 g (yield: 43%) of the desired compound, Intermediate (AA).
LC-Mass (cald: 575.24 g/mol, found: M+1 = 576 g/mol)

Synthesis of Compound B



[0249] 14.5 g (25.2 mmol) of Intermediate (AA), 11.8 g (37.8 mmol) of 2,2'-dibromo-1,1'-biphenyl, 1.45 g (2.52 mmol) of Pd2(dba)3, 2.52 ml (50% in toluene, 5.04 mmol) of tri-tert-butylphosphine (ttbp), and 4.84 g (50.4 mmol) of sodium tert-butoxide were added to 85 ml of xylene and mixed. The mixed solution was heated and stirred at a temperature of 120°C. After completion of the reaction, the resulting reaction solution was cooled to room temperature, filtered through silica gel under reduced pressure. The filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 2.74 g (yield: 15%) of the desired compound, Compound B.
LC-Mass (cald: 725.28 g/mol, found: M+1 = 726 g/mol)

Example 1



[0250] A glass substrate with an indium tin oxide (ITO) electrode (i.e., a first electrode or an anode) having a thickness of 150 nm (1,500 Å) thereon was ultrasonically cleaned by using distilled water. After completing the washing of the glass substrate using distilled water, the glass substrate was ultrasonically washed again using iso-propyl alcohol, acetone, and methanol, and then dried. The glass substrate was transported to a plasma washing machine, washed using oxygen plasma for 5 minutes, and then transported to a vacuum evaporator.

[0251] Compounds HT3 and HP-1 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 10 nm (100 Å), Compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 130 nm (1,300 Å), and mCP was deposited on the hole transport layer to form an electron blocking layer having a thickness of 10 nm (100 Å), thereby forming a hole transport region.

[0252] Compound 1 (as a host) and Compound FIr6 (as a dopant having an amount of 10 percent by weight, wt%) were co-deposited on the hole transport region to form an emission layer having a thickness of 40 nm (400 Å).

[0253] BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 10 nm (100 Å), Compound ET3 and Liq were vacuum-deposited together on the hole blocking layer to form an electron transport layer having a thickness of 30 nm (300 Å), and Liq was deposited on the electron transport layer to form an electron injection layer having a thickens of 1 nm (10 Å). Then, Al was deposited on the electron injection layer to form an Al second electrode (i.e., a cathode) having a thickness of 120 (1,200 Å), thereby completing the manufacture of an organic light-emitting device.

Examples 2 to 15 and Comparative Examples 1 and 2



[0254] Organic light-emitting devices were each manufactured in the same manner as in Example 1, except that compounds shown in Table 2 were each used as a host for forming the emission layer.

Evaluation Example 1: Evaluation of characteristics of organic light-emitting device



[0255] Changes in the voltage-dependent current density, the voltage-dependent luminescence, and the voltage-dependent current efficiency of the organic light-emitting devices of Examples 1 to 15 and Comparative Examples 1 and 2 were each measured. Specific measurement methods are shown below, and the measurement results are summarized in Table 2.

(1) Measurement of changes in voltage-dependent current density



[0256] Regarding the prepared organic light-emitting devices, voltages thereof increased from 0 volts (V) to 10 V, and current values flowing across unit devices were measured using a Keithley 2400 current-voltage meter. The results were obtained by dividing the measured current values by the area.

(2) Measurement of changes in voltage-dependent luminescence



[0257] Regarding the prepared organic light-emitting devices, voltages thereof increased from 0 V to 10 V, and results were obtained by measuring luminescence at the increased voltages using a Minolta Cs-1000A luminance meter.

(3) Measurement of current efficiency



[0258] Based on voltages and the luminescence and current density measured in (1) and (2), the current efficiency (candelas per ampere, cd/A) was calculated at the same current density (10 milliamperes per square centimeters, mA/cm2).

(4) Measurement of durability



[0259] The time taken for the luminescence of the organic light-emitting devices to reach about 95% of the initial luminescence (100%) was evaluated.

[0260] In Table 2, the driving voltage, the current efficiency, and the durability values are provided in a relative manner with respect to those of the organic light-emitting device of Comparative Example 1.
Table 2
 HostDriving voltage (relative value) (%)Current efficiency (relative value) (%)Durability (relative value) (%)Color
Reference Example 1 Compound 1 102 104 105 Blue
Reference Example 2 Compound 3 104 103 105 Blue
Reference Example 3 Compound 5 91 114 121 Blue
Reference Example 4 Compound 7 94 117 117 Blue
Reference Example 5 Compound 26 87 121 124 Blue
Reference Example 6 Compound 46 101 110 109 Blue
Reference Example 7 Compound 52 95 106 114 Blue
Example 8 Compound 55 84 134 138 Blue
Example 9 Compound 95 85 140 134 Blue
Example 10 Compound 97 94 124 131 Blue
Reference Example 11 Compound 106 105 110 111 Blue
Reference Example 12 Compound 176 94 104 102 Blue
Reference Example 13 Compound 179 95 107 104 Blue
Reference Example 14 Compound 216 81 109 115 Blue
Reference Example 15 Compound 219 83 108 121 Blue
Comparative Example 1 Compound A 100 100 100 Blue
Comparative Example 2 Compound B 176 54 12 Blue












[0261] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 15 had good driving voltage, current efficiency, and lifespan characteristics, and at levels as high as those of the organic light-emitting devices of Comparative Examples 1 and 2.

[0262] As described above, a condensed cyclic compound has excellent electric characteristics and thermal stability, and thus, an organic light-emitting device including the condensed cyclic compound exhibits low driving voltage, high emission efficiency, high current efficiency, high quantum emission efficiency, and long lifespan characteristics.

[0263] It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0264] While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the scope of the following claims.


Claims

1. A condensed cyclic compound represented by Formula 1B or 1C:



wherein, in Formulae 1B, 1C and 2A,
A1 is a group represented by Formula 2A,
A11 is a single bond or *-C(R27)(R28)-*',
R1 and R2 are each independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C1-C60 alkyl group, and a C1-C60 alkoxy group; and

a C1-C60 alkyl group and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and a cyano group,

a1 and a2 are each independently an integer selected from 0 to 4, wherein the sum of a1 and a2 is 1 or more,

1, 2, 3, or 4 groups selected from R1 in the number of a1 and R2 in the number of a2 are a cyano group,

R11, R12, R21, R22, and R27 to R28 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and - B(Q6)(Q7),

R13 is the same as defined in connection with R11,

R14 is the same as defined in connection with R12,

a21, and a22 are each independently an integer selected from 0 to 4,

* and *' each indicate a binding site to a neighboring atom in a corresponding formula,

the total number of cyano groups in the condensed cyclic compound represented by Formulae 1B and 1C is 2, 3, or 4,

at least one substituent selected from substituent(s) of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C2-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

deuterium, -CD3, -CD2H, -CDH2, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;

a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -CD3, - CD2H, -CDH2, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q11)(Q12)(Q13), -N(Q14)(Q15), and -B(Q16)(Q17);

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, - CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q21)(Q22)(Q23), -N(Q24)(Q25), and -B(Q26)(Q27); and

-Si(Q31)(Q32)(Q33), -N(Q34)(Q35), and -B(Q36)(Q37), wherein

Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.


 
2. The condensed cyclic compound of claim 1, wherein R1 and R2 are each independently selected from:

hydrogen, deuterium, -F, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group; and

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, and a cyano group.


 
3. The condensed cyclic compound of claim 1 or 2, wherein
1 or 2 groups selected from R1 in the number of a1 are a cyano group, and R2 is not a cyano group; or
1 or 2 groups selected from R1 in the number of a1 are a cyano group, and 1 or 2 groups selected from R2 in the number of a2 are cyano groups; or
R1 is not a cyano group, and 1 or 2 groups selected from R2 in the number of a2 are a cyano group.
 
4. The condensed cyclic compound of any of claims 1 to 3, wherein R11, R12, R21, R22, and R27 to R28 are each independently selected from:

hydrogen, deuterium, -F, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, a cyano group, -F, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a cyano group, -F, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and -Si(Q31)(Q32)(Q33); and

-Si(Q1)(Q2)(Q3), wherein

Q1 to Q3 and Q31 to Q33 are each independently selected from hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.


 
5. The condensed cyclic compound of any of claims 1 to 4, wherein A1 in Formula 1 is selected from groups represented by Formula 2A-1:

wherein, in Formula 2A-1,
A11, R21, R22, and * are each independently the same as defined in claim 1,
R23 is the same as defined in connection with R21 in claim 1, and
R24 is the same as defined in connection with R22 in claim 1.
 
6. The condensed cyclic compound of claim 5, wherein A1 is selected from groups represented by Formula 2A-1, and at least one selected from R13, R14, R23, and R24 is a cyano group.
 
7. The condensed cyclic compound of any of claims 1 to 6, wherein the condensed cyclic compound is represented by one selected from Formulae 1B-1 to 1B-76, and 1C-1 to 1C-76:











































































wherein, in Formulae 1B-1 to 1B-76, and 1C-1 to 1C-76,

A1, R11, and R12 are each independently the same as defined in claim 1,

R8 to R10, and R10a are each independently the same as defined in connection with R1 in claim 1,

R3 to R7 are each independently the same as defined in connection with R2 in claim 1,

R13 is the same as defined in connection with R11 in claim 1, and

R14 is the same as defined in connection with R12 in claim 1, preferably wherein R3 to R10 and R10a in Formulae 1B-1 to 1B-76, and 1C-1 to 1C-76 are each independently selected from:

hydrogen, deuterium, -F, a C1-C20 alkyl group, and a C1-C20 alkoxy group; and

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of deuterium and -F.


 
8. The condensed cyclic compound of claim 1, wherein the condensed cyclic compound is selected from Compounds 54 to 100, 104 to 105, 112 to 153, 156 to 158, 291, 292, 295, 297, 298 and 300:














































 
9. A composition comprising:

a first compound and a second compound,

wherein the first compound is the condensed cyclic compound of any of claims 1 to 8, and

wherein the second compound comprises at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, an acridine-containing ring, a dihydroacridine-containing ring, and a triindolobenzene-containing ring, and does not comprise an electron withdrawing group,

wherein the electron withdrawing group is selected from:

-F, -CFH2, -CF2H, -CF3, -CN, and -NO2;

a C1-C60 alkyl group substituted with at least one selected from -F, -CFH2, - CF2H, -CF3, -CN, and -NO2;

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group that each comprise *=N-*' as a ring-forming moiety; and

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group, which each comprise *=N-*' as a ring-forming moiety and are each substituted with at least one selected from deuterium, -F, -CFH2, -CF2H, -CF3, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, preferably wherein the second compound is selected from a compound represented by Formula H-1:

        Formula H-1     Ar1-(L1)c1-Ar2



wherein, in Formulae H-1, 11, and 12,
L1 is selected from:

a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and -Si(Q11)(Q12)(Q13),

c1 is an integer selected from 1 to 10, wherein, when c1 is 2 or more, 2 or more L1 are identical to or different from each other,

Ar1 is selected from groups represented by Formulae 11 and 12,

Ar2 is selected from:

groups represented by Formulae 11 and 12, a phenyl group, and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group,

CY1 and CY2 are each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, and a dibenzothiophene group,

A21 is selected from:

a single bond, a C1-C4 alkylene group, and a C2-C4 alkenylene group; and

a C1-C4 alkylene group and a C2-C4 alkenylene group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and - Si(Q21)(Q22)(Q23),

R30, R40, and R51 are each independently selected from:

hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group; and

-Si(Q1)(Q2)(Q3),

b1 and b2 are each independently an integer selected from 0 to 10,

Q1 to Q3, Q11 to Q13, and Q21 to Q23 are each independently selected from hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group, and

* indicates a binding site to a neighboring atom, more preferably wherein Ar1 is selected from groups represented by Formulae 11-1 to 11-8 and 12-1 to 12-16, and

Ar2 is selected from:

groups represented by Formulae 11-1 to 11-8 and 12-1 to 12-16, a phenyl group, and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group

























wherein, in Formulae 11-1 to 11-8 and 12-1 to 12-16,
X11 and X13 are each independently C(R37)(R38), N(R39), O, or S,
A21, R51, and * are each independently the same as defined above,
R31 to R39 are each independently the same as defined in connection with R30 as defined above, and
R41 to R44 are each independently the same as defined in connection with R40 in claim 14, and/or wherein

i) the second compound is selected from a compound represented by Formula H-1, wherein L1 in Formula H-1 is a single bond; or

ii) the second compound is selected from compounds represented by Formulae H-1(1) to H-1(52):

































wherein, in Formulae H-1(1) to H-1(52),
Ar1 and Ar2 are each independently the same as defined above,
Y51 is C(Z53)(Z54), N(Z55), O, or S,
Z51 to Z56 are each independently selected from hydrogen, deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and -Si(Q11)(Q12)(Q13), wherein
Q11 to Q13 are each independently selected from hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, and a naphthyl group.


 
10. The composition of claim 9, wherein the second compound is selected from Compounds H-1 to H-32:
















 
11. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer, and

wherein the organic layer comprises the condensed cyclic compound of any of claims 1 to 8.


 
12. The organic light-emitting device of claim 11, further comprising:

i) a second compound, wherein the second compound comprises at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, an acridine-containing ring, a dihydroacridine-containing ring, and a triindolobenzene-containing ring and does not comprise an electron withdrawing group;

ii) an organometallic compound represented by Formula 81

        Formula 81     M(L81)n81(L82)n82;

or

iii) any combination thereof:



wherein, in Formulae 81 and 81A,

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh),

L81 is a ligand represented by Formula 81A, and n81 is an integer selected from 1 to 3, wherein, when n81 is 2 or more, 2 or more L81 are identical to or different from each other,

L82 is an organic ligand, and n82 is an integer selected from 0 to 4, wherein, when n82 is 2 or more, 2 or more L82 are identical to or different from each other,

Y81 to Y84 are each independently carbon (C) or nitrogen (N),

Y81 and Y82 are linked via a single bond or a double bond, and Y83 and Y84 are linked via a single bond or a double bond,

CY81 and CY82 are each independently selected from a C5-C30 carbocyclic group and a C3-C30 heterocarbocyclic group,

CY81 and CY82 are optionally further linked via an organic linking group,

R81 to R85 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q81)(Q82)(Q83), -N(Q84)(Q85), -B(Q86)(Q87) and -P(=O)(Q88)(Q89),

a81 to a83 are each independently an integer selected from 0 to 5,

wherein, when a81 is 2 or more, 2 or more R81 are identical to or different from each other; when a82 is 2 or more, 2 or more R82 are identical to or different from each other; when a81 is 2 or more, 2 or more adjacent R81 are optionally linked to each other to form a saturated or unsaturated C2-C30 ring or a saturated or unsaturated C2-C30 ring substituted with at least one R88; when a82 is 2 or more, 2 or more adjacent R82 are optionally linked to each other to form a saturated or unsaturated C2-C30 ring or a saturated or unsaturated C2-C30 ring substituted with at least one R89,

R88 is the same as defined in connection with R81,

R89 is the same as defined in connection with R82,

* and *' in Formula 81A each independently indicate a binding site to M of Formula 81,

at least one substituent selected from substituent(s) of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and -Si(Q91)(Q92)(Q93),

Q81 to Q89 and Q91 to Q93 are each independently selected from hydrogen, deuterium, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and

the electron withdrawing group is selected from:

-F, -CFH2, -CF2H, -CF3, -CN, and -NO2;

a C1-C60 alkyl group substituted with at least one selected from -F, -CFH2, - CF2H, -CF3, -CN, and -NO2;

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group that each comprise *=N-*' as a ring-forming moiety; and

a C1-C60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group that each comprises *=N-*' as a ring-forming moiety and are each substituted with at least one selected from deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.


 
13. The organic light-emitting device of claim 12, wherein Y81 is N, Y82 and Y83 are each independently C, and Y84 is N or C,
CY81 and CY82 are each independently selected from a cyclopentadiene group, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corozene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, an indazole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenentrididine group, an acridine group, phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a benzocarbazole group, a dibenzocarbazole group, an imidazopyridine group, an imidazopyrimidine group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilol group, and a 2,3-dihydro-1 H-imidazole group,
R81 and R82 are each independently selected from:

hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, C1-C20 alkyl group, and a C1-C20 alkoxy group;

a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, - CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, - CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-B(Q86)(Q87) and -P(=O)(Q88)(Q89), and

Q86 to Q89 are each independently selected from:

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, - CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group.


 
14. The organic light-emitting device of claim 12 or 13, wherein, in Formula 81A, at least one selected from R81 in the number of a81 and R82 in the number of a82 is a cyano group or deuterium.
 
15. The organic light-emitting device of any of claims 12 to 14, wherein the emission layer comprises a host and a dopant,
wherein

i) the host comprises the condensed cyclic compound represented by Formula 1, and the dopant comprises the organometallic compound represented by Formula 81;

ii) the host comprises the condensed cyclic compound represented by Formula 1 and the second compound; or

iii) the host comprises the condensed cyclic compound represented by Formula 1 and the second compound, and the dopant comprises the organometallic compound represented by Formula 81.


 


Ansprüche

1. Kondensierte zyklische Verbindung, dargestellt durch Formel 1B oder 1C:



wobei in Formeln 1B, 1C und 2A,
A1 eine durch Formel 2A dargestellte Gruppe ist,
A11 eine Einfachbindung oder *-C(R27)(R28)-*' ist,
R1 und R2 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Cyanogruppe, einer C1-C60-Alkylgruppe und einer C1-C60-Alkoxygruppe, und

einer C1-C60-Alkylgruppe und einer C1-C60-Alkoxygruppe, die jeweils substituiert sind mit mindestens einem, ausgewählt aus Deuterium, -F, -Cl, -Br, -I und einer Cyanogruppe,

a1 und a2 jeweils unabhängig voneinander eine ganze Zahl sind, ausgewählt aus 0 bis 4, wobei die Summe von a1 und a2 1 oder mehr ist,

1, 2, 3 oder 4 Gruppen sind, ausgewählt aus R1 in der Anzahl von a1 und R2 in der Anzahl von a2 eine Cyanogruppe sind,

R11, R12, R21, R22 und R27 bis R28 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder ein Salz davon, einer substituierten oder unsubstituierten C1-C60-Alkylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkenylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkinylgruppe, einer substituierten oder unsubstituierten C1-C60-Alkoxygruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkylgruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkenylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkenylgruppe, einer substituierten oder unsubstituierten C6-C60-Arylgruppe, einer substituierten oder unsubstituierten C6-C60-Aryloxygruppe, einer substituierten oder unsubstituierten C6-C60-Arylthiogruppe, einer substituierten oder unsubstituierten C1-C60-Heteroarylgruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5) und - B(Q6)(Q7),

R13 identisch mit der Definition in Verbindung mit R11 ist,

R14 identisch mit der Definition in Verbindung mit R12 ist,

a21 und a22 jeweils unabhängig voneinander eine ganze Zahl sind, ausgewählt aus 0 bis 4,

* und *' jeweils eine Bindungsstelle zu einem benachbarten Atom in einer entsprechenden Formel sind,

die Gesamtzahl der Cyanogruppen in der kondensierten zyklischen Verbindung, dargestellt durch Formeln 1B und 1C 2, 3 oder 4 ist,

mindestens ein Substituent, ausgewählt aus Substituent(en) der substituierten C1-C60-Alkylgruppe, der substituierten C2-C60-Alkenylgruppe, der substituierten C2-C60-Alkinylgruppe, der substituierten C2-C60-Alkoxygruppe, der substituierten C3-C10-Cycloalkylgruppe, der substituierten C1-C10-Heterocycloalkylgruppe, der substituierten C3-C10-Cycloalkenylgruppe, der substituierten C1-C10-Heterocycloalkenylgruppe, der substituierten C6-C60-Arylgruppe, der substituierten C6-C60-Aryloxygruppe, der substituierten C6-C60-Arylthiogruppe, der substituierten C1-C60-Heteroarylgruppe, der substituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und der substituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe ausgewählt ist aus:

Deuterium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60 Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe und einer C1-C60-Alkoxygruppe,

einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe und einer C1-C60-Alkoxygruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe, einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, -Si(Q11)(Q12)(Q13), -N(Q14)(Q15) und -B(Q16)(Q17),

einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe,

einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe, einer C1-C60-Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe, einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, -Si(Q21)(Q22)(Q23), -N(Q24)(Q25) und -B(Q26)(Q27), und

-Si(Q31)(Q32)(Q33), -N(Q34)(Q35), und -B(Q36)(Q37), wobei

Q1 bis Q7, Q11 bis Q17, Q21 bis Q27 und Q31 bis Q37 jeweils unabhängig ausgewählt sind aus Wasserstoff. Deuterium, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkynylgruppe, einer C1-C60 Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heteroycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe.


 
2. Kondensierte zyklische Verbindung nach Anspruch 1, wobei R1 und R2 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, -F, einer Cyanogruppe, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, und

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, die jeweils substituiert sind mit mindestens einem, ausgewählt aus Deuterium, -F und einer Cyanogruppe.


 
3. Kondensierte zyklische Verbindung nach Anspruch 1 oder 2, wobei

1 oder 2 Gruppen, ausgewählt aus R1 in der Anzahl von a1 eine Cyanogruppe sind und R2 keine Cyanogruppe ist, oder

1 oder 2 Gruppen, ausgewählt aus R1 in der Anzahl von a1 eine Cyanogruppe sind und 1 oder 2 Gruppen, ausgewählt aus R2 in der Anzahl von a2 Cyanogruppen sind, oder

R1 keine Cyanogruppe ist und 1 oder 2 aus R2 in der Anzahl von a2 ausgewählte Gruppen eine Cyanogruppe sind.


 
4. Kondensierte zyklische Verbindung eines der Ansprüche 1 bis 3, wobei R11, R12, R21, R22 und R27 bis R28 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, -F, einer Cyanogruppe, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe,

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer Cyanogruppe, -F, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe und einer Naphthylgruppe,

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe und einer Dibenzothiophenylgruppe,

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe und einer Dibenzothiophenylgruppe, die jeweils substituiert sind mit mindestens einem, ausgewählt aus Deuterium, einer Cyanogruppe, -F, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, eine Napthylgruppe und -Si(Q31)(Q32)(Q33), und

-Si(Q1)(Q2)(Q3), wobei

Q1 bis Q3 und Q31 bis Q33 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe und einer Naphthylgruppe.


 
5. Kondensierte zyklische Verbindung eines der Ansprüche 1 bis 4, wobei A1 in Formel 1 ausgewählt ist aus Gruppen, die durch Formel 2A-1 dargestellt sind:

wobei in Formel 2A-1,
A11, R21, R22 und * jeweils unabhängig voneinander identisch mit der Definition in Anspruch 1 sind, R23 identisch mit der Definition in Verbindung mit R21 in Anspruch 1 ist, und R24 identisch mit der Definition in Verbindung mit R22 in Anspruch 1 ist.
 
6. Kondensierte zyklische Verbindung nach Anspruch 5, wobei A1 ausgewählt ist aus Gruppen, die durch Formel 2A-1 dargestellt sind, und mindestens eine aus R13, R14, R23 und R24 ausgewählte eine Cyanogruppe ist.
 
7. Kondensierte zyklische Verbindung eines der Ansprüche 1 bis 6, wobei die kondensierte zyklische Verbindung dargestellt ist durch eine Verbindung, die aus Formeln 1B-1 bis 1B-76 und 1C-1 bis 1C-76 ausgewählt ist:











































































wobei in Formeln 1B-1 bis 1B-76 und 1C-1bis 1C-76,

A1, R11 und R12 jeweils unabhängig voneinander identisch mit der Definition in Anspruch 1 sind,

R8 bis R10, und R10a jeweils unabhängig voneinander identisch mit der Definition in Verbindung mit R1 in Anspruch 1 sind,

R3 bis R7 jeweils unabhängig voneinander identisch mit der Definition in Verbindung mit R2 in Anspruch 1 sind,

R13 identisch mit der Definition in Verbindung mit R11 in Anspruch 1 ist, und

R14 identisch mit der Definition in Verbindung mit R12 in Anspruch 1 ist, wobei vorzugsweise R3 bis R10 und R10a in Formeln 1B-1 bis 1B-76 und 1C-1 bis 1C-76 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, -F, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, und

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert mit mindestens einem von Deuterium und -F.


 
8. Kondensierte zyklische Verbindung nach Anspruch 1, wobei die kondensierte zyklische Verbindung ausgewählt ist aus den Verbindungen 54 bis 100, 104 bis 105, 112 bis 153, 156 bis 158, 291, 292, 295, 297, 298 und 300:














































 
9. Zusammensetzung, umfassend:

eine erste Verbindung und eine zweite Verbindung,

wobei die erste Verbindung die kondensierte zyklische Verbindung nach einem der Ansprüche 1 bis 8 ist, und

wobei die zweite Verbindung mindestens eine umfasst, ausgewählt aus einem carbazolhaltigen Ring, einem dibenzofuranhaltigen Ring, einem dibenzothiophenhaltigen Ring, einem inddenocarbazolhaltigen Ring, einem indolocarbazolhaltigen Ring, einem benzofurocarbazolhaltigen Ring, einem benzothienocarbazolhaltigen Ring, einem acridinhaltigen Ring, einem dihydroacridinhaltigen Ring und einem tris-indolbenzolhaltigen Ring, und keine elektonenentziehende Gruppe umfasst,

wobei die elektronenentziehende Gruppe ausgewählt ist aus:

-F, -CFH2, -CF2H, -CF3, -CN und -NO2,

einer C1-C60-Alkylgruppe, substituiert mit mindestens einem, ausgewählt aus -F, -CFH2, -CF2H, -CF3, -CN, and -NO2,

einer C1-C60-Heteroarylgruppe und einer monovalenten nicht-aromatischen kondensierten polyzyklischen heterozyklischen Gruppe, die jeweils *=N-*' als ringförmigen Anteil umfassen, und einer C1-C60-Heteroarylgruppe und einer monovalenten nicht-aromatischen kondensierten polyzyklischen heterozyklischen Gruppe, die jeweils *=N-*' als ringförmigen Anteil umfassen und jeweils substituiert sind mit mindestens einem aus Deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer substituierten oder unsubstituierten C1-C60-Alkylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkenylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkinylgruppe, einer substituierten oder unsubstituierten C1-C60-Alkoxygruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkylgruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkenylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkenylgruppe, einer substituierten oder unsubstituierten C6-C60-Arylgruppe, einer substituierten oder unsubstituierten C6-C60-Aryloxygruppe, einer substituierten oder unsubstituierten C6-C60-Arylthiogruppe, einer substituierten oder unsubstituierten C1-C60-Heteroarylgruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, wobei vorzugsweise die zweite Verbindung ausgewählt ist aus einer von Formel H-1 dargestellten Verbindung :

        Formel H-1     Ar1-(L1)c1-Ar2



wobei in Formeln H-1, 11 und 12,
L1 ausgewählt ist aus:

einer Einfachbindung, einer Phenylengruppe, einer Naphthylengruppe, einer Fluorenylengruppe, einer Carbazolylengruppe, einer Dibenzofuranylengruppe und einer Dibenzothiophenylengruppe, und

einer Carbazolylengruppe, einer Dibenzofuranylengruppe und einer Dibenzothiophenylengruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer C1-C10-Alkylgruppe, einer C1-C10-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Biphenylgruppe und -Si(Q11)(Q12)(Q13),

c1 eine ganze Zahl ist, ausgewählt aus 1 bis 10, wobei, wenn c1 2 oder mehr ist, 2 oder mehr L1 miteinander identisch oder voneinander verschieden sind,

Ar1 ausgewählt ist aus Gruppen, die durch Formeln 11 und 12 dargestellt sind,

Ar2 ausgewählt ist aus:

durch Formeln 11 und 12 dargestellten Gruppen, einer Phenylgruppe und einer Naphthylgruppe, und

einer Phenylgruppe und einer Naphthylgruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe und einer Biphenylgruppe,

CY1 und CY2 jeweils unabhängig voneinander ausgewählt sind aus einer Benzolgruppe, einer Naphthalingruppe, einer Fluorengruppe, einer Carbazolgruppe, einer Benzocarbazolgruppe, einer Indolocarbazolgruppe, einer Dibenzofurangruppe und einer Dibenzothiophengruppe,

A21 ausgewählt ist aus:

einer Einfachbindung, einer C1-C4-Alkylengruppe und einer C2-C4-Alkenylengruppe, und

einer C1-C4-Alkylengruppe und einer C2-C4-Alkenylengruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer C1-C10-Alkylgruppe, einer C1-C10-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Biphenylgruppe und - Si(Q21)(Q22)(Q23),

R30, R40 und R51 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe,

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe und einer Dibenzothiophenylgruppe,

einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe und einer Dibenzothiophenylgruppe,

einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe und einer Dibenzothiophenylgruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe und einer Biphenylgruppe, und

-Si(Q1)(Q2)(Q3),

b1 und b2 jeweils unabhängig voneinander eine ganze Zahl sind, ausgewählt aus 0 bis 10,

Q1 bis Q3, Q11 bis Q13 und Q21 bis Q23 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe und einer Biphenylgruppe, und

* eine Bindungsstelle an ein benachbartes Atom anzeigt, wobei stärker bevorzugt Ar1 ausgewählt ist aus Gruppen, die durch Formeln 11-1 bis 11-8 und 12-1 bis 12-16 dargestellt sind, und

Ar2 ausgewählt ist aus:

Gruppen, dargestellt durch Formeln 11-1 bis 11-8 und 12-1 bis 12-16, einer Phenylgruppe und einer Naphthylgruppe, und

einer Phenylgruppe und einer Naphthylgruppe, jeweils substituiert mit mindestens einem, ausgewählt aus Deuterium, einer Hydroxygruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe und einer Biphenylgruppe

























wobei in Formeln 11-1 bis 11-8 und 12-1 bis 12-16
X11 und X13 jeweils unabhängig voneinander C(R37)(R38), N(R39), O oder S sind,
A21, R51 und * jeweils unabhängig voneinander identisch mit obiger Definition sind,
R31 bis R39 jeweils unabhängig voneinander identisch mit obiger Definition in Verbindung mit R30 sind, und
R41 bis R44 jeweils unabhängig voneinander identisch mit der Definition in Verbindung mit R40 in Anspruch 14 sind, und/oder wobei

i) die zweite Verbindung ausgewählt ist aus einer von Formel H-1 dargestellten Verbindung, wobei L1 in Formel H-1 eine Einfachbindung ist, oder

ii) die zweite Verbindung ausgewählt ist aus von Formeln H-1(1) bis H-1(52) dargestellten Verbindungen:

































wobei in Formeln H-1(1) bis H-1(52)
Ar1 und Ar2 jeweils unabhängig voneinander identisch mit obiger Definition sind,
Y51C(Z53)(Z54), N(Z55), O oder S ist,
Z51 bis Z56 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, Deuterium, einer C1-C10-Alkylgruppe, einer C1-C10-Alkoxygruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Biphenylgruppe und -Si(Q11)(Q12)(Q13), wobei
Q11 bis Q13 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, einer C1-C10-Alkylgruppe, einer C1-C10-Alkoxygruppe, einer Phenylgruppe und einer Naphthylgruppe.


 
10. Zusammensetzung nach Anspruch 9, wobei die zweite Verbindung ausgewählt ist aus den Verbindungen H-1 bis H-32:
















 
11. Organische lichtemittierende Vorrichtung, umfassend:

eine erste Elektrode,

eine zweite Elektrode, und

eine zwischen der ersten Elektrode und der zweiten Elektrode angeordnete organische Schicht,

wobei die organische Schicht eine Emissionsschicht umfasst, und

wobei die organische Schicht die kondensierte zyklische Verbindung nach einem der Ansprüche 1 bis 8 umfasst.


 
12. Organische lichtemittierende Vorrichtung nach Anspruch 11, ferner umfassend:

i) eine zweite Verbindung, wobei die zweite Verbindung mindestens eine umfasst, ausgewählt aus einem carbazolhaltigen Ring, einem dibenzofuranhaltigen Ring, einem dibenzothiophenhaltigen Ring, einem inddenocarbazolhaltigen Ring, einem indolocarbazolhaltigen Ring, einem benzofurocarbazolhaltigen Ring, einem benzothienocarbazolhaltigen Ring, einem akridinhaltigen Ring, einem dihydroacridinhaltigen Ring und einem tris-indolbenzolhaltigen Ring, und keine elektonenentziehende Gruppe umfasst,

ii) eine Organometallverbindung, dargestellt durch Formel 81

        Formel 81      M(L81)n81(L82)n82,

oder

iii) eine beliebige Kombination davon:



wobei in Formeln 81 und 81A

M ausgewählt ist aus Iridium (Ir), Platin (Pt), Osmium (Os), Titan (Ti), Zirkonium (Zr), Hafnium (Hf), Europium (Eu), Terbium (Tb), Thulium (Tm) und Rhodium (Rh),

L81 ein durch Formel 81A dargestellter Ligand ist und n81 eine ganze Zahl ist, ausgewählt aus 1 bis 3, wobei, wenn n81 2 oder mehr ist, 2 oder mehr L81 miteinander identisch oder voneinander verschieden sind,

L82 ein organischer Ligand ist, und n82 eine ganze Zahl ist, ausgewählt aus 0 bis 4, wobei, wenn n82 2 oder mehr ist, 2 oder mehr L82 miteinander identisch oder voneinander verschieden sind,

Y81 bis Y84 jeweils unabhängig voneinander Kohlenstoff (C) oder Stickstoff (N) sind,

Y81 und Y82 über eine Einfachbindung oder eine Doppelbindung verknüpft sind und Y83 und Y84 über eine Einfachbindung oder eine Doppelbindung verknüpft sind,

CY81 und CY82 jeweils unabhängig voneinander ausgewählt sind aus einer carbozyklischen C5-C30-Gruppe und einer heterocarbozyklischen C3-C30-Gruppe,

CY81 und CY82 wahlweise ferner über eine organische Verknüpfungsgruppe verknüpft sind,

R81 bis R85 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, -SF5, einer substituierten oder unsubstituierten C1-C60-Alkylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkenylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkinylgruppe, einer substituierten oder unsubstituierten C1-C60-Alkoxygruppe, einer substituierten oder unsubstituierten C3-C10-ycloalkylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkylgruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkenylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkenylgruppe, einer substituierten oder unsubstituierten C6-C60-Arylgruppe, einer substituierten oder unsubstituierten C6-C60-Aryloxygruppe, einer substituierten oder unsubstituierten C6-C60-Arylthiogruppe, einer substituierten oder unsubstituierten C1-C60-Heteroarylgruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, -Si(Q81)(Q82)(Q83), -N(Q84)(Q85), -B(Q86)(Q87) und -P(=O)(Q88)(Q89),

a81 bis a83 jeweils unabhängig voneinander eine aus 0 bis 5 ausgewählte ganze Zahl sind,

wobei, wenn a81 2 oder mehr ist, 2 oder mehr R81 miteinander identisch oder voneinander verschieden sind, wenn a82 2 oder mehr ist, 2 oder mehr R82 miteinander identisch oder voneinander verschieden sind, wenn a81 2 oder mehr ist, 2 oder mehr benachbarte R81 wahlweise miteinander verknüpft sind, um einen gesättigten oder ungesättigten C2-C30-Ring oder einen gesättigten oder ungesättigten C2-C30-Ring zu bilden, der mit mindestens einem R88 substituiert ist, wenn a82 2 oder mehr ist, 2 oder mehr benachbarte R82 wahlweise miteinander verknüpft sind, um einen gesättigten oder ungesättigten C2-C30-Ring oder einen gesättigten oder ungesättigten C2-C30-Ring zu bilden, der mit mindestens einem R89 substituiert ist,

R88 identisch mit der Definition in Verbindung mit R81 ist,

R89 identisch mit der Definition in Verbindung mit R82 ist,

* und *' in Formel 81A jeweils unabhängig voneinander eine Bindungsstelle zu M von Formel 81 anzeigen,

mindestens einen Substituenten, ausgewählt aus den Substituenten der substituierten C1-C60-Alkylgruppe, der substituierten C2-C60-Alkenylgruppe, der substituierten C2-C60-Alkinyl-gruppe, der substituierten C1-C60-Alkoxygruppe, der substituierten C3-C10-Cycloalkylgruppe, der substituierten C1-C10-Heterocycloalkylgruppe, der substituierten C3-C10-Cycloalkenylgruppe, der substituierten C1-C10-Heterocycloalkenylgruppe, der substituierten C6-C60-Arylgruppe, der substituierten C6-C60-Aryloxygruppe, der substituierten C6-C60-Arylthiogruppe, der substituierten C1-C60-Heteroarylgruppe, der substituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und der substituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe ausgewählt ist aus Deuterium, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe, einer C1-C60-Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe, einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe und -Si(Q91)(Q92)(Q93),

Q81 bis Q89 und Q91 bis Q93 jeweils unabhängig voneinander ausgewählt sind aus Wasserstoff, Deuterium, einer C1-C60-Alkylgruppe, einer C1-C60-Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C1-C60-Heteroarylgruppe, einer monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe, und

die elektronenentziehende Gruppe ausgewählt ist aus:

-F, -CFH2, -CF2H, -CF3, -CN und -NO2,

einer C1-C60-Alkylgruppe, substituiert mit mindestens einem, ausgewählt aus -F, -CFH2, -CF2H, -CF3, -CN und -NO2,

einer C1-C60-Heteroarylgruppe und einer monovalenten nicht-aromatischen kondensierten polyzyklischen heterozyklischen Gruppe, die jeweils *=N-*' als ringförmigen Anteil umfassen, und einer C1-C60-Heteroarylgruppe und einer monovalenten nicht-aromatischen kondensierten polyzyklischen heterozyklischen Gruppe, die jeweils *=N-*' als ringförmigen Anteil umfassen und jeweils substituiert sind mit mindestens einem aus Deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer substituierten oder unsubstituierten C1-C60-Alkylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkenylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkinylgruppe, einer substituierten oder unsubstituierten C1-C60-Alkoxygruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkylgruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkenylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkenylgruppe, einer substituierten oder unsubstituierten C6-C60-Arylgruppe, einer substituierten oder unsubstituierten C6-C60-Aryloxygruppe, einer substituierten oder unsubstituierten C6-C60-Arylthiogruppe, einer substituierten oder unsubstituierten C1-C60-Heteroarylgruppe, einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten polyzyklischen Gruppe und einer substituierten oder unsubstituierten monovalenten nicht-aromatischen kondensierten heteropolyzyklischen Gruppe.


 
13. Organische lichtemittierende Vorrichtung nach Anspruch 12, wobei Y81 N ist, Y82 und Y83 jeweils unabhängig voneinander C sind, und Y84 N oder C ist,
CY81 und CY82 jeweils unabhängig voneinander ausgewählt sind aus einer Cyclopentadiengruppe, einer Benzolgruppe, einer Heptalengruppe, einer Indengruppe, einer Naphthalingruppe, einer Azulengruppe, einer Heptalengruppe, einer Indacengruppe, einer Acenaphthylengruppe, einer Fluorgruppe, einer Spirobifluorengruppe, einer Benzofluorengruppe, einer Dibenzofluorengruppe, einer Phenalengruppe, einer Phenanthrengruppe, einer Anthracengruppe, einer Fluoranthengruppe, einer Triphenylengruppe, einer Pyrengruppe, einer Chrysengruppe, einer Naphthacengruppe, einer Picengruppe, einer Perylengruppe, einer Pentafengruppe, einer Hexacengruppe, einer Pentacengruppe, einer Rubicingruppe, einer Coronengruppe, einer Ovalengruppe, einer Pyrrolgruppe, einer Isoindolgruppe, einer Indolgruppe, einer Indazolgruppe, einer Pyrazolgruppe, einer Imidazolgruppe, einer Triazolgruppe, einer Oxazolgruppe, einer Isoxazolgruppe, einer Oxadiazolgruppe, einer Thiazolgruppe, einer Isothiazolgruppe, einer Thiadiazolgruppe, einer Puringruppe, einer Furangruppe, einer Thiophengruppe, einer Pyridingruppe, einer Pyrimidingruppe, einer Chinolingruppe, einer Isochinolingruppe, einer Benzochinolingruppe, einer Phthalazingruppe, einer Naphthyridingruppe, einer Chinoxalingruppe, einer Chinazolingruppe, einer Cinnolingruppe, einer Phenentridingruppe, einer Acridingruppe, einer Phenanthrolingruppe, einer Phenazingruppe, einer Benzimidazolgruppe, einer Benzofurangruppe, einer Benzothiophengruppe, einer Isobenzothiazolgruppe, einer Benzoxazolgruppe, einer Isobenzoxazolgruppe, einer Benzocarbazolgruppe, einer Dibenzocarbazolgruppe, einer Imidazopyridingruppe, einer Imidazopyrimidingruppe, einer Dibenzofurangruppe, einer Dibenzothiophengruppe, einer Dibenzothiophensulfongruppe, einer Carbazolgruppe, einer Dibenzosilingruppe und einer 2,3-Dihydro-1H-imidazolgruppe,
R81 und R82 jeweils unabhängig voneinander ausgewählt sind aus:

Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, -SF5, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe,

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert mit mindestens einem ausgewählt aus Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C10-Alkylgruppe, einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Pyridinylgruppe und einer Pyrimidinylgruppe,

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Quinolinylgruppe, einer Isoquinolinylgruppe, einer Benzoquinolinylgruppe, einer Quinoxalinylgruppe, einer Quinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzooxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe und einer Imidazopyrimidinylgruppe,

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Quinolinylgruppe, einer Isoquinolinylgruppe, einer Benzoquinolinylgruppe, einer Quinoxalinylgruppe, einer Quinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzooxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe und einer Imidazopyrimidinylgruppe, jeweils substituiert mit mindestens einem ausgewählt aus einem Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, einer Hydroxygruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Quinolinylgruppe, einer Isoquinolinylgruppe, einer Benzoquinolinylgruppe, einer Quinoxalinylgruppe, einer Quinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzooxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe und einer Imidazopyrimidinylgruppe, und

-B(Q86)(Q87) und -P(=O)(Q88)(Q89), und

Q86 bis Q89 jeweils unabhängig voneinander ausgewählt sind aus:

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H und -CD2CDH2,

einer n-Propylgruppe, einer Iso-Propylgruppe, einer n-Butylgruppe, einer Iso-Butylgruppe, einer sec-Butylgruppe, einer tert-Butylgruppe, einer n-Pentylgruppe, einer Iso-Pentylgruppe, einer sec-Pentylgruppe, einer tert-Pentylgruppe, einer Phenylgruppe und einer Naphthylgruppe,

und einer n-Propylgruppe, einer Iso-Propylgruppe, einer n-Butylgruppe, einer Isobutylgruppe, einer sec-Butylgruppe, einer tert-Butylgruppe, einer n-Pentylgruppe, einer Iso-Pentylgruppe, einer sec-Pentylgruppe, einer tert-Pentylgruppe, einer Phenylgruppe und einer Naphthylgruppe, die jeweils mit mindestens einer Deuteriumgruppe substituiert sind, einer C1-C10-Alkylgruppe und einer Phenylgruppe.


 
14. Organische lichtemittierende Vorrichtung nach Anspruch 12 oder 13, wobei in Formel 81A mindestens eine, ausgewählt aus R81 in der Anzahl von a81 und R82 in der Anzahl von a82, eine Cyanogruppe oder Deuterium ist.
 
15. Organische lichtemittierende Vorrichtung nach einem der Ansprüche 12 bis 14, wobei die Emissionsschicht einen Wirt und ein Dotierstoff umfasst, wobei

i) der Wirt die von Formel 1 dargestellte kondensierte zyklische Verbindung umfasst, und der Dotierstoff die von Formel 81 dargestellte Organometallverbindung umfasst,

ii) der Wirt die von Formel 1 dargestellte kondensierte zyklische Verbindung und die zweite Verbindung umfasst, oder

iii) der Wirt die von Formel 1 dargestellte kondensierte zyklische Verbindung und die zweite Verbindung umfasst, und der Dotierstoff die von Formel 81 dargestellte Organometallverbindung umfasst.


 


Revendications

1. Composé cyclique condensé représenté par la formule 1B ou 1C :



dans lequel, dans les formules 1B, 1C et 2A,
A1 est un groupe représenté par la formule 2A,
A11 est une liaison simple ou *-C(R27)(R28)-*',
R1 et R2 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe cyano, un groupe alkyle en C1-C60, et un groupe alcoxy en C1-C60 ;

et un groupe alkyle en C1-C60 et un groupe alcoxy en C1-C60, chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, -Cl, -Br, -I, et un groupe cyano,

a1 et a2 représentent chacun indépendamment un nombre entier compris entre 0 et 4, dans lequel la somme de a1 et de a2 est supérieure ou égale à 1,

1, 2, 3, ou 4 groupes choisis parmi R1 dans le nombre de a1 et R2 dans le nombre de a2 sont un groupe cyano,

R11, R12, R21, R22, et R27 à R28 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60 substitué ou non substitué, un groupe alcényle en C2-C60 substitué ou non substitué, un groupe alcynyle en C2-C60 substitué ou non substitué, un groupe alcoxy en C1-C60 substitué ou non substitué, un groupe cycloalkyle en C3-C10 substitué ou non substitué, un groupe hétérocycloalkyle en C1-C10 substitué ou non substitué, un groupe cycloalcényle en C3-C10 substitué ou non substitué, un groupe hétérocycloalcényle en C1-C10 substitué ou non substitué, un groupe aryle en C6-C60 substitué ou non substitué, un groupe aryloxy en C6-C60 substitué ou non substitué, un groupe arylthio en C6-C60 substitué ou non substitué, un groupe hétéroaryle en C1-C60 substitué ou non substitué, un groupe polycyclique condensé non aromatique monovalent substitué non substitué, un groupe hétéropolycyclique condensé non aromatique monovalent substitué non substitué, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), et - B(Q6)(Q7),

R13 est le même que défini en connexion avec R11,

R14 est le même que défini en connexion avec R12,

a21, et a22 représentent chacun indépendamment un nombre entier compris entre 0 et 4,

* et *' indiquent chacun un site de liaison à un atome voisin dans une formule correspondante, le nombre total de groupes cyano dans le composé cyclique condensé représenté par les formules 1B et 1C est 2, 3, ou 4,

au moins un substituant choisi parmi le ou les substituants du groupe alkyle en C1-C60 substitué, du groupe alcényle en C2-C60 substitué, du groupe alcynyle en C2-C60 substitué, du groupe alcoxy en C2-C60 substitué, du groupe cycloalkyle en C3-C10 substitué, du groupe hétérocycloalkyle en C1-C10 substitué, du groupe cycloalcényle en C3-C10 substitué, du groupe hétérocycloalcényle en C1-C10 substitué, du groupe aryle en C6-C60 substitué, du groupe aryloxy en C6-C60 substitué, du groupe arylthio en C6-C60 substitué, du groupe hétéroaryle en C1-C60 substitué, du groupe polycyclique condensé non aromatique monovalent substitué, et le groupe hétéropolycyclique condensé non aromatique monovalent substitué est choisi parmi :

le deutérium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60, un groupe alcényle en C2-C60, un groupe alcynyle en C2-C60, et un groupe alcoxy en C1-C60 ;

un groupe alkyle en C1-C60, un groupe alcényle en C2-C60, un groupe alcynyle en C2-C60 et un groupe alcoxy en C1-C60, chacun étant substitué par au moins un groupe choisi parmi le deutérium, -CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, -Si(Q11)(Q12)(Q13), -N(Q14)(Q15), et -B(Q16)(Q17) ;

un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, et un groupe hétéropolycyclique condensé non aromatique monovalent ;

un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, et un groupe hétéropolycyclique condensé non aromatique monovalent, chacun étant substitué par au moins un groupe choisi parmi le deutérium, - CD3, -CD2H, -CDH2, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60, un groupe alcényle en C2-C60, un groupe alcynyle en C2-C60, un groupe alcoxy en C1-C60, un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, -Si(Q21)(Q22)(Q23), -N(Q24)(Q25), et -B(Q26)(Q27) ;

et -Si(Q31)(Q32)(Q33), -N(Q34)(Q35), et -B(Q36)(Q37), dans lequel Q1 à Q7, Q11 à Q17, Q21 à Q27, et Q31 à Q37 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60, un groupe alcényle en C2-C60, un groupe alcynyle en C2-C60, un groupe alcoxy en C1-C60, un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, et un groupe hétéropolycyclique condensé non aromatique monovalent.


 
2. Composé cyclique condensé selon la revendication 1, dans lequel R1 et R2 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, -F, un groupe cyano, un groupe alkyle en C1-C20, et un groupe alcoxy en C1-C20 ;

et un groupe alkyle en C1-C20 et un groupe alcoxy en C1-C20, chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, et un groupe cyano.


 
3. Composé cyclique condensé selon la revendication 1 ou 2, dans lequel 1 ou 2 des groupes choisis parmi R1 dans le nombre de a1 sont un groupe cyano, et R2 n'est pas un groupe cyano ;
ou 1 ou 2 groupes choisis parmi R1 dans le nombre de a1 sont un groupe cyano, et 1 ou 2 groupes choisis parmi R2 dans le nombre de a2 sont des groupes cyano ;
ou R1 n'est pas un groupe cyano, et 1 ou 2 groupes choisis parmi R2 dans le nombre de a2 sont un groupe cyano.
 
4. Composé cyclique condensé selon l'une quelconque des revendications 1 à 3, dans lequel R11, R12, R21, R22, et R27 à R28 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, -F, un groupe cyano, un groupe alkyle en C1-C20, et un groupe alcoxy en C1-C20 ;

un groupe alkyle en C1-C20 et un groupe alcoxy en C1-C20, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe cyano, -F, un groupe phényle, un groupe biphényle, un groupe terphényle, et un groupe naphtyle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, et un groupe dibenzothiophényle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, et un groupe dibenzothiophényle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe cyano, -F, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe naphtyle, et -Si(Q31)(Q32)(Q33) ;

et -Si(Q1)(Q2)(Q3), dans lequel Q1 à Q3 et Q31 à Q33 sont chacun indépendamment choisis parmi l'hydrogène, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe phényle, un groupe biphényle, un groupe terphényle, et un groupe naphtyle.


 
5. Composé cyclique condensé selon l'une quelconque des revendications 1 à 4, dans lequel A1 dans la Formule 1 est choisi parmi les groupes représentés par la formule 2A-1 :

dans lequel, dans la Formule 2A-1,
A11, R21, R22, et * représentent chacun indépendamment le même que défini dans la revendication 1,
R23 est le même que défini en connexion avec R21 dans la revendication 1, et R24 est le même que défini en connexion avec R22 dans la revendication 1.
 
6. Composé cyclique condensé selon la revendication 5, dans lequel A1 est choisi parmi des groupes représentés par la formule 2A-1, et au moins un groupe choisi parmi R13, R14, R23, et R24 est un groupe cyano.
 
7. Composé cyclique condensé selon l'une quelconque des revendications 1 à 6, dans lequel le composé cyclique condensé est représenté par un groupe choisi parmi les formules 1B-1 à 1B-76, et 1C-1 à 1C-76 :











































































dans lequel, dans les formules 1B-1 à 1B-76, et 1C-1 à 1C-76,

A1, R11, et R12 représentent chacun indépendamment le même que défini dans la revendication 1,

R8 à R10, et R10a représentent chacun indépendamment le même que défini en connexion avec R1 dans la revendication 1,

R3 à R7 représentent chacun indépendamment le même que défini en connexion avec R2 dans la revendication 1,

R13 est le même que défini en connexion avec R11 dans la revendication 1, et

R14 est le même que défini en connexion avec R12 dans la revendication 1, de préférence dans lequel R3 à R10 et R10a dans les formules 1B-1 à 1B-76, et 1C-1 à 1C-76 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, -F, un groupe alkyle en C1-C20, et un groupe alcoxy en C1-C20 ;

et un groupe alkyle en C1-C20 et un groupe alcoxy en C1-C20, chacun étant substitué par au moins un parmi le deutérium et -F.


 
8. Composé cyclique condensé selon la revendication 1, dans lequel le composé cyclique condensé est choisi parmi les composés 54 à 100, 104 à 105, 112 à 153, 156 à 158, 291, 292, 295, 297, 298 et 300 :














































 
9. Composition comprenant :

un premier composé et un second composé,

dans laquelle le premier composé est le composé cyclique condensé selon l'une quelconque des revendications 1 à 8, et

dans laquelle le second composé comprend au moins un groupe choisi parmi un noyau contenant un carbazole, un noyau contenant un dibenzofurane, un noyau contenant un dibenzothiophène, un noyau contenant un indénocarbazole, un noyau contenant un indolocarbazole, un noyau contenant un benzofurocarbazole, un noyau contenant un benzothiénocarbazole, un noyau contenant une acridine, un noyau contenant une dihydroacridine, et un noyau contenant un triindolobenzène, et ne comprend pas de groupe électroattracteur,

dans lequel le groupe électroattracteur est choisi parmi :

-F, -CFH2, -CF2H, -CF3, -CN, et -NO2 ;

un groupe alkyle en C1-C60 substitué par au moins un groupe choisi parmi -F, -CFH2, -CF2H, -CF3, -CN, et -NO2 ;

un groupe hétéroaryle en C1-C60 et un groupe hétérocyclique polycyclique condensé non aromatique monovalent qui comprennent chacun *=N-*' en tant que fraction formant un noyau ; et un groupe hétéroaryle en C1-C60 et un groupe hétérocyclique polycyclique condensé non aromatique monovalent, qui comprennent chacun *=N-*' en tant que fraction formant un noyau et chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60 substitué ou non substitué, un groupe alcényle en C2-C60 substitué ou non substitué, un groupe alcynyle en C2-C60 substitué ou non substitué, un groupe alcoxy en C1-C60 substitué ou non substitué, un groupe cycloalkyle en C3-C10 substitué ou non substitué, un groupe hétérocycloalkyle en C1-C10 substitué ou non substitué, un groupe cycloalcényle en C3-C10 substitué ou non substitué, un groupe hétérocycloalcényle en C1-C10 substitué ou non substitué, un groupe aryle en C6-C60 substitué ou non substitué, un groupe aryloxy en C6-C60 substitué ou non substitué, un groupe arylthio en C6-C60 substitué ou non substitué, un groupe hétéroaryle en C1-C60 substitué ou non substitué, un groupe polycyclique condensé non aromatique monovalent substitué non substitué, et un groupe hétéropolycyclique condensé non aromatique monovalent substitué ou non substitué, de préférence dans lequel le second composé est choisi parmi un composé représenté par la formule H-1 :

        Formule H-1     Ar1-(L1)c1-Ar2



dans lequel, dans les formules H-1, 11, et 12,
L1 est choisi parmi :

une liaison simple, un groupe phénylène, un groupe naphtylène, un groupe fluorenylène, un groupe carbazolylène, un groupe dibenzofuranylène, et un groupe dibenzothiophénylène ;

et un groupe carbazolylène, un groupe dibenzofuranylène, et un groupe dibenzothiophénylène, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe alkyle en C1-C10, un groupe alcoxy en C1-C10, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe biphényle, et -Si(Q11)(Q12)(Q13),

c1 est un nombre entier compris entre 1 et 10, dans lequel, lorsque c1 vaut au moins 2, au moins 2 L1 sont identiques ou différents l'un de l'autre,

Ar1 est choisi parmi des groupes représentés par les formules 11 et 12,

Ar2 est choisi parmi :

des groupes représentés par les formules 11 et 12, un groupe phényle, et un groupe naphtyle ;

et un groupe phényle et un groupe naphtyle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, et un groupe biphényle,

CY1 et CY2 sont chacun indépendamment choisis parmi un groupe benzène, un groupe naphtalène, un groupe fluorène, un groupe carbazole, un groupe benzocarbazole, un groupe indolocarbazole, un groupe dibenzofurane, et un groupe dibenzothiophène,

A21 est choisi parmi :

une liaison simple, un groupe alkylène en C1-C4, et un groupe alcénylène en C2-C4 ; et

un groupe alkylène en C1-C4 et un groupe alcénylène en C2-C4, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe alkyle en C1-C10, un groupe alcoxy en C1-C10, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe biphényle, et -Si(Q21)(Q22)(Q23),

R30, R40, et R51 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C20, et un groupe alcoxy en C1-C20 ;

un groupe alkyle en C1-C20 et un groupe alcoxy en C1-C20, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, et un groupe dibenzothiophényle ;

un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, et un groupe dibenzothiophényle ;

un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, et un groupe dibenzothiophényle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, et un groupe biphényle ;

et -Si(Q1)(Q2)(Q3),

b1 et b2 représentent chacun indépendamment un nombre entier compris entre 0 et 10,

Q1 à Q3, Q11 à Q13, et Q21 à Q23 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, et un groupe biphényle, et

* indique un site de liaison à un atome voisin, plus préférablement dans lequel Ar1 est choisi parmi des groupes représentés par les formules 11-1 à 11-8 et 12-1 à 12-16, et

Ar2 est choisi parmi :

les groupes représentés par les formules 11-1 à 11-8 et 12-1 à 12-16, un groupe phényle, et un groupe naphtyle ;

et un groupe phényle et un groupe naphtyle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe hydroxyle, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, et un groupe biphényle

























dans lequel, dans les formules 11-1 à 11-8 et 12-1 à 12-16,
X11 et X13 représentent chacun indépendamment C(R37)(R38), N(R39), O, ou S,
A21, R51, et * représentent chacun indépendamment le même groupe que défini ci-dessus,
R31 à R39 représentent chacun indépendamment le même que défini en connexion avec R30 tel que défini ci-dessus, et
R41 à R44 représentent chacun indépendamment le même que défini en connexion avec R40 dans la revendication 14, et/ou dans lequel

i) le second composé est choisi parmi un composé représenté par la formule H-1, dans lequel L1 dans la formule H-1 est une liaison simple ; ou

ii) le second composé est choisi parmi les composés représentés par les formules H-1 (1) à H-1 (52) :



































dans lequel, dans les formules H-1(1) à H-1(52),
Ar1 et Ar2 représentent chacun indépendamment le même groupe que défini ci-dessus,
Y51 représente C(Z53)(Z54), N(Z55), O, ou S,
Z51 à Z56 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, un groupe alkyle en C1-C10, un groupe alcoxy en C1-C10, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe biphényle, et -Si(Q11)(Q12)(Q13), dans lequel
Q11 à Q13 sont chacun indépendamment choisis parmi l'hydrogène, un groupe alkyle en C1-C10, un groupe alcoxy en C1-C10, un groupe phényle, et un groupe naphtyle.
 
10. Composition selon la revendication 9, dans laquelle le second composé est choisi parmi les composés H-1 à H-32 :
















 
11. Dispositif organique électroluminescent comprenant :

une première électrode ;

une seconde électrode ;

et une couche organique disposée entre la première électrode et la seconde électrode,

dans lequel la couche organique comprend une couche d'émission, et dans lequel la couche organique comprend le composé cyclique condensé selon l'une quelconque des revendications 1 à 8.


 
12. Dispositif organique électroluminescent selon la revendication 11, comprenant en outre :

i) un second composé, dans lequel le second composé comprend au moins un groupe choisi parmi un noyau contenant un carbazole, un noyau contenant un dibenzofurane, un noyau contenant un dibenzothiophène, un noyau contenant un indénocarbazole, un noyau contenant un indolocarbazole, un noyau contenant un benzofurocarbazole, un noyau contenant un benzothiénocarbazole, un noyau contenant une acridine, un noyau contenant une dihydroacridine, et un noyau contenant un triindolobenzène et ne comprend pas de groupe électroattracteur ;

ii) un composé organométallique représenté par la formule 81

        Formule 81     M(L81)n81(L82)n82 ;

ou

iii) toute combinaison de ceux-ci :



dans lequel, dans les formules 81 et 81A,

M est choisi parmi l'iridium (Ir), le platine (Pt), l'osmium (Os), le titane (Ti), le zirconium (Zr), le hafnium (Hf), l'europium (Eu), le terbium (Tb), le thulium (Tm), et le rhodium (Rh),

L81 est un ligand représenté par la formule 81A, et n81 est un nombre entier compris entre 1 et 3, dans lequel, lorsque n81 vaut au moins 2, au moins 2 L81 sont identiques ou différents l'un de l'autre,

L82 et un ligand organique, et n82 est un nombre entier compris entre 0 et 4, dans lequel, lorsque n82 vaut au moins 2, au moins 2 L82 sont identiques ou différents l'un de l'autre,

Y81 à Y84 représentent chacun indépendamment le carbone (C) ou l'azote (N),

Y81 et Y82 sont liés par l'intermédiaire d'une liaison simple ou d'une double liaison, et Y83 et Y84 sont liés par l'intermédiaire d'une liaison simple ou d'une double liaison,

CY81 et CY82 sont chacun indépendamment choisis parmi un groupe carbocyclique en C5-C30 et un groupe hétérocarbocyclique en C3-C30,

CY81 et CY82 sont éventuellement en outre liés par l'intermédiaire d'un groupe de liaison organique,

R81 à R85 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, -SF5, un groupe alkyle en C1-C60 substitué ou non substitué, un groupe alcényle en C2-C60 substitué ou non substitué, un groupe alcynyle en C2-C60 substitué ou non substitué, un groupe alcoxy en C1-C60 substitué ou non substitué, un groupe cycloalkyle en C3-C10 substitué ou non substitué, un groupe hétérocycloalkyle en C1-C10 substitué ou non substitué, un groupe cycloalcényle en C3-C10 substitué ou non substitué, un groupe hétérocycloalcényle en C1-C10 substitué ou non substitué, un groupe aryle en C6-C60 substitué ou non substitué, un groupe aryloxy en C6-C60 substitué ou non substitué, un groupe arylthio en C6-C60 substitué ou non substitué, un groupe hétéroaryle en C1-C60 substitué ou non substitué, un groupe polycyclique condensé non aromatique monovalent substitué non substitué, un groupe hétéropolycyclique condensé non aromatique monovalent substitué non substitué, -Si(Q81)(Q82)(Q83), -N(Q84)(Q85), -B(Q86)(Q87) et -P(=O)(Q88)(Q89),

a81 à a83 représentent chacun indépendamment un nombre entier compris entre 0 et 5, dans lequel, lorsque a81 vaut au moins 2, au moins 2 R81 sont identiques ou différents l'un de l'autre ; lorsque a82 vaut au moins 2, au moins 2 R82 sont identiques ou différents l'un de l'autre ; lorsque a81 vaut au moins 2, au moins 2 R81 adjacents sont éventuellement liés l'un à l'autre pour former un noyau en C2-C30 saturé ou insaturé ou un noyau en C2-C30 saturé ou insaturé substitué par au moins un R88 ; lorsque a82 vaut au moins 2, au moins 2 R82 adjacents sont éventuellement liés l'un à l'autre pour former un noyau en C2-C30 saturé ou insaturé ou un noyau en C2-C30 saturé ou insaturé substitué par au moins un R89,

R88 est le même que défini en connexion avec R81,

R89 est le même que défini en connexion avec R82,

* et *' dans la Formule 81A indiquent chacun indépendamment un site de liaison à M de Formule 81,

au moins un substituant choisi parmi le ou les substituants du groupe alkyle en C1-C60 substitué, du groupe alcényle en C2-C60 substitué, du groupe alcynyle en C2-C60 substitué, du groupe alcoxy en C1-C60 substitué, du groupe cycloalkyle en C3-C10 substitué, du groupe hétérocycloalkyle en C1-C10 substitué, du groupe cycloalcényle en C3-C10 substitué, du groupe hétérocycloalcényle en C1-C10 substitué, du groupe aryle en C6-C60 substitué, du groupe aryloxy en C6-C60 substitué, du groupe arylthio en C6-C60 substitué, du groupe hétéroaryle en C1-C60 substitué, du groupe polycyclique condensé non aromatique monovalent substitué, et le groupe hétéropolycyclique condensé non aromatique monovalent substitué est choisi parmi le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60, un groupe alcényle en C2-C60, un groupe alcynyle en C2-C60, un groupe alcoxy en C1-C60, un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe aryloxy en C6-C60, un groupe arylthio en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, et -Si(Q91)(Q92)(Q93),

Q81 à Q89 et cinq Q91 à Q93 sont chacun indépendamment choisis parmi l'hydrogène, le deutérium, un groupe alkyle en C1-C60, un groupe alcoxy en C1-C60, un groupe cycloalkyle en C3-C10, un groupe hétérocycloalkyle en C1-C10, un groupe cycloalcényle en C3-C10, un groupe hétérocycloalcényle en C1-C10, un groupe aryle en C6-C60, un groupe hétéroaryle en C1-C60, un groupe polycyclique condensé non aromatique monovalent, et un groupe hétéropolycyclique condensé non aromatique monovalent, et

le groupe électroattracteur est choisi parmi :

-F, -CFH2, -CF2H, -CF3, -CN, et -NO2 ;

un groupe alkyle en C1-C60 substitué par au moins un groupe choisi parmi -F, -CFH2, -CF2H, -CF3, -CN, et -NO2 ;

un groupe hétéroaryle en C1-C60 et un groupe hétérocyclique polycyclique condensé non aromatique monovalent qui comprennent chacun *=N-*' en tant que fraction formant un noyau ; et un groupe hétéroaryle en C1-C60 et un groupe hétérocyclique polycyclique condensé non aromatique monovalent qui comprennent chacun *=N-*' en tant que fraction formant un noyau et chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C60 substitué ou non substitué, un groupe alcényle en C2-C60 substitué ou non substitué, un groupe alcynyle en C2-C60 substitué ou non substitué, un groupe alcoxy en C1-C60 substitué ou non substitué, un groupe cycloalkyle en C3-C10 substitué ou non substitué, un groupe hétérocycloalkyle en C1-C10 substitué ou non substitué, un groupe cycloalcényle en C3-C10 substitué ou non substitué, un groupe hétérocycloalcényle en C1-C10 substitué ou non substitué, un groupe aryle en C6-C60 substitué ou non substitué, un groupe aryloxy en C6-C60 substitué ou non substitué, un groupe arylthio en C6-C60 substitué ou non substitué, un groupe hétéroaryle en C1-C60 substitué ou non substitué, un groupe polycyclique condensé non aromatique monovalent substitué non substitué, et un groupe hétéropolycyclique condensé non aromatique monovalent substitué ou non substitué.


 
13. Dispositif organique électroluminescent selon la revendication 12, dans lequel Y81 représente N, Y82 et Y83 représentent chacun indépendamment C, et Y84 représente N ou C,
CY81 et CY82 représentent chacun indépendamment choisi parmi un groupe cyclopentadiène, un groupe benzène, un groupe heptalène, un groupe indène, un groupe naphtalène, un groupe azulène, un groupe heptalène, un groupe indacène, un groupe acénaphtylène, un groupe fluorène, un groupe spino-bifluorène, un groupe benzofluorène, un groupe dibenzofluorène, un groupe phénalène, un groupe phénanthrène, un groupe anthracène, un groupe fluoranthène, un groupe triphénylène, un groupe pyrène, un groupe chrysène, un groupe naphtacène, un groupe picène, un groupe pérylène, un groupe pentaphène, un groupe hexacène, un groupe pentacène, un groupe rubicène, un groupe corozène, un groupe ovalène, un groupe pyrrole, un groupe isoindole, un groupe indole, un groupe indazole, un groupe pyrazole, un groupe imidazole, un groupe triazole, un groupe oxazole, un groupe isoxazole, un groupe oxadiazole, un groupe thiazole, un groupe isothiazole, un groupe thiadiazole, un groupe purine, un groupe furane, un groupe thiophène, un groupe pyridine, un groupe pyrimidine, un groupe quinoline, un groupe isoquinoline, un groupe benzoquinoline, un groupe phtalazine, un groupe naphtyridine, un groupe quinoxaline, un groupe quinazoline, un groupe cinnoline, un groupe phénentrididine, un groupe acridine, un groupe phénanthroline, un groupe phénazine, un groupe benzimidazole, un groupe benzofurane, un groupe benzothiophène, un groupe isobenzothiazole, un groupe benzoxazole, un groupe isobenzoxazole, un groupe benzocarbazole, un groupe dibenzocarbazole, un groupe imidazopyridine, un groupe imidazopyrimidine, un groupe dibenzofurane, un groupe dibenzothiophène, un groupe dibenzothiophène sulfone, un groupe carbazole, un groupe dibenzosilol, et un groupe 2,3- dihydro-1H-imidazole,
R81 et R82 sont chacun indépendamment choisis parmi :

l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, -SF5, un groupe alkyle en C1-C20, et un groupe alcoxy en C1-C20 ;

un groupe alkyle en C1-C20 et un groupe alcoxy en C1-C20, chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, - CFH2, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C10, un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclooctyle, un groupe adamantanyle, un groupe norbornanyle, un groupe norbornényle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe naphtyle, un groupe pyridinyle, et un groupe pyrimidinyle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclooctyle, un groupe adamantanyle, un groupe norbornanyle, un groupe norbornényle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysène, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe imidazolyle, un groupe pyrazolyle, un groupe thiazolyle, un groupe isothiazolyle, un groupe oxazolyle, un groupe isoxazolyle, un groupe pyridinyle, un groupe pyrazinyle, un groupe pyrimidinyle, un groupe pyridazinyle, un groupe isoindolyle, un groupe indolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe quinoxalinyle, un groupe quinazolinyle, un groupe cinnolinyle, un groupe carbazolyle, un groupe phénanthrolinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe isobenzothiazolyle, un groupe benzoxazolyle, un groupe isobenzoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe benzocarbazolyle, un groupe dibenzocarbazolyle, un groupe imidazopyridinyle et un groupe imidazopyrimidinyle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclooctyle, un groupe adamantanyle, un groupe norbornanyle, un groupe norbornényle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysène, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe imidazolyle, un groupe pyrazolyle, un groupe thiazolyle, un groupe isothiazolyle, un groupe oxazolyle, un groupe isoxazolyle, un groupe pyridinyle, un groupe pyrazinyle, un groupe pyrimidinyle, un groupe pyridazinyle, un groupe isoindolyle, un groupe indolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe quinoxalinyle, un groupe quinazolinyle, un groupe cinnolinyle, un groupe carbazolyle, un groupe phénanthrolinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe isobenzothiazolyle, un groupe benzoxazolyle, un groupe isobenzoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe benzocarbazolyle, un groupe dibenzocarbazolyle, un groupe imidazopyridinyle et un groupe imidazopyrimidinyle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, - CF2H, -CFH2, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amino, un groupe amidino, un groupe hydrazine, un groupe hydrazone, un groupe acide carboxylique ou un sel de celui-ci, un groupe acide sulfonique ou un sel de celui-ci, un groupe acide phosphorique ou un sel de celui-ci, un groupe alkyle en C1-C20, un groupe alcoxy en C1-C20, un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclooctyle, un groupe adamantanyle, un groupe norbornanyle, un groupe norbornényle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe cycloheptényle, un groupe phényle, un groupe naphtyle, un groupe fluorényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysène, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe imidazolyle, un groupe pyrazolyle, un groupe thiazolyle, un groupe isothiazolyle, un groupe oxazolyle, un groupe isoxazolyle, un groupe pyridinyle, un groupe pyrazinyle, un groupe pyrimidinyle, un groupe pyridazinyle, un groupe isoindolyle, un groupe indolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe quinoxalinyle, un groupe quinazolinyle, un groupe cinnolinyle, un groupe carbazolyle, un groupe phénanthrolinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe isobenzothiazolyle, un groupe benzoxazolyle, un groupe isobenzoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe benzocarbazolyle, un groupe dibenzocarbazolyle, un groupe imidazopyridinyle, et un groupe imidazopyrimidinyle ;

et -B(Q86)(Q87) et -P(=O)(Q88)(Q89), et

Q86 à Q89 sont chacun indépendamment choisis parmi :

-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, et -CD2CDH2 ;

un groupe n-propyle, un groupe iso-propyle, un groupe n-butyle, un groupe iso-butyle, un groupe sec-butyle, un groupe tert-butyle, un groupe n-pentyle, un groupe iso-pentyle, un groupe sec-pentyle, un groupe tert-pentyle, un groupe phényle, et un groupe naphtyle ;

et un groupe n-propyle, un groupe iso-propyle, un groupe n-butyle, un groupe iso-butyle, un groupe sec-butyle, un groupe tert-butyle, un groupe n-pentyle, un groupe iso-pentyle, un groupe sec-pentyle, un groupe tert-pentyle, un groupe phényle et un groupe naphtyle, chacun étant substitué par au moins un groupe choisi parmi le deutérium, un groupe alkyle en C1-C10, et un groupe phényle.


 
14. Dispositif organique électroluminescent selon la revendication 12 ou la revendication 13, dans lequel, dans la Formule 81A, au moins un groupe choisi parmi R81 dans le nombre de a81 et R82 dans le nombre de a82 est un groupe cyano ou le deutérium.
 
15. Dispositif organique électroluminescent selon l'une quelconque des revendications 12 à 14, dans lequel la couche d'émission comprend un hôte et un dopant, dans lequel

i) l'hôte comprend le composé cyclique condensé représenté par la formule 1, et le dopant comprend le composé organométallique représenté par la formule 81 ;

ii) l'hôte comprend le composé cyclique condensé représenté par la formule 1 et le second composé ; ou

iii) l'hôte comprend le composé cyclique condensé représenté par la formule 1 et le second composé, et le dopant comprend le composé organométallique représenté par la formule 81.


 




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Patent documents cited in the description