(19)
(11)EP 3 486 250 B1

(12)EUROPEAN PATENT SPECIFICATION

(45)Mention of the grant of the patent:
24.06.2020 Bulletin 2020/26

(21)Application number: 18206760.3

(22)Date of filing:  16.11.2018
(51)Int. Cl.: 
C07F 15/00  (2006.01)
H01L 51/00  (2006.01)
C09K 11/07  (2006.01)

(54)

ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

ORGANOMETALLISCHE VERBINDUNG UND ORGANISCHE LICHTEMITTIERENDE VORRICHTUNG DAMIT

COMPOSÉ ORGANOMÉTALLIQUE ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE L'INCLUANT


(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: 21.11.2017 KR 20170155814

(43)Date of publication of application:
22.05.2019 Bulletin 2019/21

(73)Proprietor: Samsung Display Co., Ltd.
Gyeonggi-Do (KR)

(72)Inventors:
  • JEON, Mina
    Gyeonggi-do (KR)
  • KO, Soobyung
    Gyeonggi-do (KR)
  • KIM, Sungbum
    Gyeonggi-do (KR)
  • AHN, Heechoon
    Gyeonggi-do (KR)
  • JUN, Mieun
    Gyeonggi-do (KR)
  • HAN, Junghoon
    Gyeonggi-do (KR)
  • KIM, Youngkook
    Gyeonggi-do (KR)
  • HWANG, Seokhwan
    Gyeonggi-do (KR)

(74)Representative: Shearman, James Ward 
Marks & Clerk LLP 15 Fetter Lane
London EC4A 1BW
London EC4A 1BW (GB)


(56)References cited: : 
WO-A1-2015/171627
  
  • BOERNER, LEIGH J. K. ET AL: "Spin-state control of thermal and photochemical Bergman cyclization", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM), vol. 49, no. 21, 29 January 2013 (2013-01-29), pages 2145-2147, XP002789099, ISSN: 1359-7345
  
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

BACKGROUND


1. Field



[0001] One or more embodiments of the present disclosure relate to an organometallic compound and an organic light-emitting device including the same.

2. Description of the Related Art



[0002] Organic light-emitting devices are self-emission devices that can produce full-color images, and may also have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed, compared to devices in the related art.

[0003] An example organic light-emitting device may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) may recombine in the emission layer to produce excitons. These excitons may transition from an excited state to a ground state to thereby generate light. WO 2015/171627 A1 relates to stabilized imidazophenanthridine materials.

SUMMARY



[0004] One or more embodiments of the present disclosure relate to a novel organometallic compound and an organic light-emitting device including the same.

[0005] Additional aspects of embodiments 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.

[0006] One or more aspects of embodiments of the present disclosure provide an organometallic compound represented by Formula 1:



[0007] In Formula 1,
M11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
A11 to A16 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
Y11 to Y14 are each independently N or C,
T11 to T14 are each independently selected from a single bond, *-O-*', and *-S-*',
L11 to L13 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-C(R17)=C(R18)-*', *-C(=O)-*', *-C(=S)-*', *-C=C-*', *-B(R17)-*', *-N(R17)-*', *-P(R17)-*', *-Si(R17)(R18)-*', *-P(R17)(R18)-*', and *-Ge(R17)(R18)-*',
a11 to a13 are each independently selected from 0, 1, 2, and 3,
when a11 is zero, A11 and A12 are not linked (e.g., bonded) to each other,
when a12 is zero, A12 and A13 are not linked (e.g., bonded) to each other,
when a13 is zero, A13 and A14 are not linked (e.g., bonded) to each other,
R11 to R18 are each independently selected from hydrogen, deuterium, -F, - CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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),-B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1),-P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2),
R16 and R11, or R17 and R14 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R14 and R15, or R15 and R16 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R17 and R11, R17 and R12, or R17 and R13 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b11 to b16 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
* and *' each indicate a binding site to a neighboring atom,
at least one substituent of the substituted C4-C60 carbocyclic group, the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C2-C60 heterocyclic group, 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:

deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, -F, - CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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(Q11)(Q12)(Q13),-N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11), -S(=O)2(Q11), and -P(=O)(Q11)(Q12);

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, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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(Q21)(Q22), -B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21), and -P(=O)(Q21)(Q22); and

-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, -F, and a cyano group; a C6-C60 aryl group substituted with at least one selected from deuterium, -F, and a cyano group; a biphenyl group, and a terphenyl group.



[0008] One or more aspects of embodiments of the present disclosure provide an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer and at least one species of the organometallic compound.

[0009] At least some of the above and other features of the present invention are set out in the claims.

BRIEF DESCRIPTION OF THE DRAWING



[0010] These and/or other aspects of embodiments will become apparent and more readily appreciated from the following description of the example embodiments, taken in conjunction with the accompanying drawing (FIG. 1), which is a schematic view of an organic light-emitting device according to an embodiment of the present disclosure.

DETAILED DESCRIPTION



[0011] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawing, wherein like reference numerals refer to like elements throughout and duplicative descriptions thereof may not be provided. 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 accompanying drawing, to explain aspects of embodiments of the present disclosure. 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" and "one of", when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. An organometallic compound according to an embodiment of the present disclosure is represented by Formula 1:





[0012] M11 in Formula 1 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0013] In some embodiments, M11 may be selected from Pt, Pd, Cu, Ag, and Au.

[0014] For example, M11 may be Pt, but embodiments of the present disclosure are not limited thereto.

[0015] A11 to A16 in Formula 1 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group.

[0016] For example, A11 to A16 in Formula 1 may each independently be selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group. For example, A11 to A16 in Formula 1 may each independently be selected from a C5-C30 carbocyclic group and a C1-C20 heterocyclic group. For example, A11 to A16 in Formula 1 may each independently be selected from a C5-C20 carbocyclic group and a C1-C20 heterocyclic group.

[0017] In some embodiments, A11 to A16 may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indeno pyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0018] In some embodiments, A11 to A13 may each independently be represented by one of Formulae 2-1 to 2-43:















[0019] In Formulae 2-1 to 2-43,
X21 to X23 are each independently selected from C(R24) and C-*, provided that at least two of X21 to X23 are C-*,
X24 is N-*, and X25 and X26 are each independently selected from C(R24) and C-*, provided that at least one of X25 and X26 is C-*,
X27 and X28 are each independently selected from N, N(R25), and N-*, and X29 is selected from C(R24) and C-*, provided that i) at least one of X27 and X28 is N-*, and X29 is C-*, or ii) X27 and X28 are each N-*, and X29 is C(R24),
R21 to R24 are each independently the same as described in connection with R11 in Formula 1,
b21 is selected from 1, 2, and 3,
b22 is selected from 1, 2, 3, 4, and 5,
b23 is selected from 1, 2, 3, and 4,
b24 is selected from 1 and 2, and
* indicates a binding site to a neighboring atom.

[0020] In one or more embodiments, A14 to A16 may each independently be represented by one of Formulae 2-1 to 2-4:



[0021] In Formulae 2-1 to 2-4,
X21 to X23 are each independently selected from C(R24) and C-*, provided that at least two of X21 to X23 are C-*,
X24 is N-*, and X25 and X26 are each independently selected from C(R24) and C-*, provided that at least one of X25 and X26 is C-*,
R21 to R22 are each independently the same as described in connection with R11 in Formula 1,
b21 is selected from 1, 2, and 3, and
* indicates a binding site to a neighboring atom.

[0022] In some embodiments, in Formula 1,
a moiety represented by

may be a moiety represented by one of Formulae 1-1 to 1-64:

































[0023] In Formulae 1-1 to 1-64,
Y14 is the same as described above, and
*, *', and *" each indicate a binding site to a neighboring atom.

[0024] In one or more embodiments, in Formula 1,
a moiety represented by

may be a moiety represented by one of Formulae 1-1, 1-3, and 1-10:



[0025] In Formulae 1-1, 1-3, and 1-10,
Y14 is the same as described above, and
*, *', and *" each indicate a binding site to a neighboring atom.
Y11 to Y14 in Formula 1 are each independently N or C.

[0026] In some embodiments, Y11, Y12, and Y13 may each be C, and Y14 may be N;
Y11, Y12, and Y14 may each be C, and Y13 may be N;
Y11, Y13, and Y14 may each be C, and Y12 may be N;
Y12, Y13, and Y14 may each be C, and Y11 may be N;
Y11 and Y14 may each be C, and Y12 and Y13 may each be N;
Y11 and Y14 may each be N, and Y12 and Y13 may each be C;
Y11 and Y12 may each be C, and Y13 and Y14 may each be N;
Y11 and Y12 may each be N, and Y13 and Y14 may each be C;
Y11 and Y13 may each be C, and Y12 and Y14 may each be N; or
Y11 and Y13 may each be N, and Y12 and Y14 may each be C.
T11 to T14 in Formula 1 are each independently selected from a single bond, *-O-*', and *-S-*'.

[0027] In some embodiments, T11 to T14 may each be a single bond at the same time (e.g., concurrently or simultaneously);
T11 may be selected from *-O-*' and *-S-*', and T12 to T14 may each independently be a single bond;
T12 may be selected from *-O-*' and *-S-*', and T11, T13, and T14 may each independently be a single bond;
T13 may be selected from *-O-*' and *-S-*', and T11, T12, and T14 may each independently be a single bond; or
T14 may be selected from *-O-*' and *-S-*', and T11, T12, and T13 may each independently be a single bond.

[0028] L11 to L13 in Formula 1 are each independently selected from a single bond, *-O-*' *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-C(R17)=C(R18)-*', *-C(=O)-*', *-C(=S)-*', *-C=C-*', *-B(R17)-*', *-N(R17)-*', *-P(R17)-*', *-Si(R17)(R18)-*', *-P(R17)(R18)-*', and *-Ge(R17)(R18)-*'.

[0029] L11 to L13 may each independently be selected from a single bond, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-B(R17)-*', *-N(R17)-*', *-Si(R17)(R18)-*', and *-P(R17)(R18)-*'.

[0030] In one or more embodiments, L11 may be *-N(R17)-*', *-C(R17)(R18)-*', or *-Si(R17)(R18)-*', and R17 and R12 may be linked (e.g., coupled) to form a substituted or unsubstituted C1-C60 (e.g. C1-C20) heterocyclic group,
L12 may be *-N(R17)-*', *-C(R17)(R18)-*', or *-Si(R17)(R18)-*', and R17 and R13 may be linked (e.g., coupled) to form a substituted or unsubstituted C1-C60 (e.g. C1-C20) heterocyclic group.

[0031] In Formula 1, a11 to a13 are each independently selected from 0, 1, 2, and 3,
when a11 is zero, A11 and A12 are not linked (e.g., coupled) to each other, when a12 is zero, A12 and A13 are not linked (e.g., coupled) to each other, and when a13 is zero, A13 and A14 are not linked (e.g., coupled) to each other.

[0032] In some embodiments, a11, a12, and a13 may each independently be selected from 1, 2, and 3;
when a11 is zero, a12 and a13 may each independently be selected from 0, 1, 2, and 3;
when a12 is zero, a11 and a13 may each independently be selected from 0, 1, 2, and 3; or
when a13 is zero, a11 and a12 may each independently be selected from 0, 1, 2, and 3.

[0033] In one or more embodiments, a11 may be 0, and a12 and a13 may each independently be selected from 1, 2, and 3;
when a12 is zero, a11 and a13 may each independently be selected from 1, 2, and 3; or
when a13 is zero, a11 and a12 may each independently be selected from 1, 2, and 3.

[0034] In some embodiments, a11 may be zero, but embodiments of the present disclosure are not limited thereto.

[0035] In Formula 1, R11 to R18 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) alkyl group, a substituted or unsubstituted C2-C60 (e.g. C2-C20) alkenyl group, a substituted or unsubstituted C2-C60 (e.g. C2-C20) alkynyl group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a substituted or unsubstituted C6-C60 (e.g. C6-C30) aryloxy group, a substituted or unsubstituted C6-C60 (e.g. C6-C30) arylthio group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroaryl group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroaryloxy group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroarylthio 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), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2),
R16 and R11, or R17 and R14 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R14 and R15, or R15 and R16 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, and
R17 and R11, R17 and R12, or R17 and R13 are optionally linked (e.g., coupled) to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group.

[0036] b11 to b16 in Formula 1 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8.

[0037] In some embodiments, R11 to R18 may each independently be selected from the group consisting of:

hydrogen, deuterium, -F, -CI, -Br, -I, 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, -F, -CI, -Br, -I, a cyano group, a phenyl group, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, an indolocarbazolyl group, - Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)(Q31), -S(=O)2(Q31),-P(=O)(Q31)(Q32), and -P(=S)(Q31)(Q32); and

-Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1),-S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), and

Q1 to Q3 and Q31 to Q33 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) heteroaryl group, a C1-C60 (e.g. C1-C20) heteroaryloxy group, a C1-C60 (e.g. C1-C20) heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 (e.g. C1-C20) alkyl group substituted with at least one selected from deuterium, -F, and a cyano group; a C6-C60 (e.g. C6-C30) aryl group substituted with at least one selected from deuterium, -F, and a cyano group; a biphenyl group, and a terphenyl group.



[0038] For example, R11 to R18 may each independently be selected from the group consisting of:

hydrogen, deuterium, -F, -CI, -Br, -I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, and a cyano group; and

a phenyl group, a naphthyl group, and a pyridinyl group, but embodiments of the present disclosure are not limited thereto.



[0039] In Formula 1, * and *' each independently indicate a binding site to a neighboring atom.

[0040] At least one substituent of the substituted C4-C60 carbocyclic group, the substituted C5-C60 carbocyclic group, the substituted C2-C60 heterocyclic group, the substituted C1-C60 heterocyclic group, 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:

deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, and a C1-C60 (e.g. C1-C20) alkoxy group;

a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, and a C1-C60 (e.g. C1-C20) alkoxy group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q11)(Q12)(Q13),-N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11), -S(=O)2(Q11), and -P(=O)(Q11)(Q12);

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) 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, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q21)(Q22)(Q23), -N(Q21)(Q22),-B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21), and -P(=O)(Q21)(Q22); and

-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 (e.g. C1-C20) alkyl group substituted with at least one selected from deuterium, -F, and a cyano group; a C6-C60 (e.g. C6-C30) aryl group substituted with at least one selected from deuterium, -F, and a cyano group; a biphenyl group, and a terphenyl group.



[0041] In some embodiments, the organometallic compound may be represented by Formula 3-1 or Formula 3-2:







[0042] In Formulae 3-1 and 3-2,
M11, A11 to A13, Y11 to Y14, T11 to T14, L11 to L13, a11 to a13, R11 to R13, and b11 to b13 are each independently the same as described herein,
Y31 to Y37 are each independently N or C,
Y41 to Y47 are each independently N or C,
R31 to R33 are each independently the same as described in connection with R14,
R41 to R43 are each independently the same as described in connection with R13,
b31, b32, b41, and b42 are each independently 1 or 2, and
b33 and b43 are each independently 1, 2, or 3.

[0043] In one or more embodiments, when the organometallic compound is represented by Formula 3-1, the organometallic compound may be represented by Formula 3-1-1 or 3-1-2:





[0044] In Formulae 3-1-1 and 3-1-2,
M11, A11, A12, Y11 to Y14, Y31 to Y37, T11 to T14, L11, L13, a11, a13, R11, R12, R31 to R33, b11, b12, and b31 to b33 are the same as described herein,
Y51 to Y55 are each independently N or C,
Y61 to Y67 are each independently N or C,
R51, R61, and R62 are each independently the same as described in connection with R13,
b51 is 1, 2, 3, or 4,
b61 is 1, 2, or 3, and
b62 is 1, 2, 3, or 4.

[0045] In one or more embodiments, when the organometallic compound is a compound represented by Formula 3-1-1, A12 may be a group represented by

R12 and b12 are each independently the same as described herein, and * and *' each indicate a binding site to a neighboring atom.

[0046] In one or more embodiments, when the organometallic compound is a group represented by Formula 3-1-1, 3-1-2, or 3-2, a11 may be zero.

[0047] In some embodiments, the organometallic compound may be selected from Compounds 1 to 45, but embodiments of the present disclosure are not limited thereto:

























[0048] The organometallic compound represented by Formula 1 includes a moiety represented by

Because of the structural characteristics arising from the way in which the aromatic rings (A14, A15, and A16) constituting the moiety are condensed, the organometallic compound may have a feature of improved energy transfer (e.g., may promote energy transfer), improve luminescent efficiency, and implement high color purity when applied to an organic light-emitting device.

[0049] When the organometallic compound represented by Formula 1 has a rigid (or substantially rigid) structure due to the inclusion of the moiety, an organic light-emitting device including the organometallic compound may have high durability and a long lifespan.

[0050] The organometallic compound may emit green light or red light. For example, the organometallic compound may emit green light or red light (bottom-emission CIEx,y color coordinates (0.14, 0.06 to 0.08)) having a maximum emission wavelength of about 500 nm to about 800 nm, for example, about 530 nm to about 750 nm, but embodiments of the present disclosure are not limited thereto. Therefore, the organometallic compound represented by Formula 1 may be suitably used for manufacturing an organic light-emitting device that emits deep green light and/or deep red light.

[0051] Suitable synthesis methods of the organometallic compound represented by Formula 1 may be recognized by those of ordinary skill in the art with reference to the Examples provided below.

[0052] At least one kind or species of the organometallic compound of Formula 1 may be used between a pair of electrodes in an organic light-emitting device. For example, the organometallic compound may be included in an emission layer. The organometallic compound included in the emission layer may act as a dopant.

[0053] Accordingly, provided is an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer includes at least one organometallic compound represented by Formula 1.

[0054] The expression "(an organic layer) includes at least one organometallic compound" as used herein may include a case in which "(an organic layer) includes identical (e.g., substantially identical) compounds represented by Formula 1" (e.g., all molecules having the structure of Formula 1 are the same) as well as a case in which "(an organic layer) includes two or more different organometallic compounds (e.g., two or more compounds having different structures) represented by Formula 1."

[0055] For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may be included in an emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be included in the same layer (for example, Compound 1 and Compound 2 may both be included in an emission layer), or in different layers (for example, Compound 1 may be included in an emission layer and Compound 2 may be included in an electron transport region).

[0056] According to one or more embodiments,
the first electrode of the organic light-emitting device may be an anode,
the second electrode of the organic light-emitting device may be a cathode,
the organic layer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode,
the hole transport region may include a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0057] The term "organic layer" as used herein may refer to a single layer and/or a plurality of layers between the first electrode and the second electrode of the organic light-emitting device. The material included in the "organic layer" is not limited to being an organic material.

[0058] In one or more embodiments, the emission layer may include the organometallic compound represented by Formula 1. The emission layer may further include a host, and an amount of the host in the emission layer may be larger than an amount of the organometallic compound in the emission layer.

[0059] In some embodiments, for example, the host may include a carbazole-containing compound.

[0060] In some embodiments, the hole transport region may include an electron blocking layer, and the electron blocking layer may include the organometallic compound.

[0061] In some embodiments, the electron transport region may include a hole blocking layer, which may include the organometallic compound.

[0062] In some embodiments, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV.

[0063] In some embodiments, the electron transport region may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound or a silyl-containing compound.

Description of the Accompanying Drawing



[0064] The accompanying drawing is a schematic view of an organic light-emitting device 10 according to an embodiment of the present disclosure. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0065] Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment of the present disclosure and a method of manufacturing the organic light-emitting device 10 will be described in connection with the accompanying drawing.

First electrode 110



[0066] In the accompanying drawing, a substrate may be under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance.

[0067] The first electrode 110 may be formed by depositing and/or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials with a high work function in order to facilitate hole injection.

[0068] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming a first electrode may be selected from magnesium (Mg), silver (Ag), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but embodiments of the present disclosure are not limited thereto.

[0069] The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.

Organic layer 150



[0070] The organic layer 150 may be on the first electrode 110. The organic layer 150 may include an emission layer.

[0071] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.

Hole transport region in organic layer 150



[0072] The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

[0073] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

[0074] For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein the constituting layers in each structure are sequentially stacked from the first electrode 110 in the stated order, but the structure of the hole transport region is not limited thereto.

[0075] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:













[0076] In Formulae 201 and 202,
L201 to L204 may each independently be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 (e.g. C6-C32) arylene group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
L205 may be selected from *-O-*', *-S-*', *-N(Q201)-*', a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 (e.g. C6-C32) arylene group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xa1 to xa4 may each independently be an integer of 0 to 3,
xa5 may be an integer of 1 to 10, and
R201 to R204 and Q201 may each independently be selected from 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 (e.g. C6-C32) aryl group, a substituted or unsubstituted C6-C60 (e.g. C6-C32) aryloxy group, a substituted or unsubstituted C6-C60 (e.g. C6-C32) arylthio group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0077] For example, in Formula 202, R201 and R202 may optionally be linked (e.g., coupled) via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203 and R204 may optionally be linked (e.g., coupled) via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

[0078] In one or more embodiments, in Formulae 201 and 202,

[0079] L201 to L205 may each independently be selected from the group consisting of:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with -F, 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 benzofluorenyl group, a dibenzofluorenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, -Si(Q31)(Q32)(Q33), and -N(Q31)(Q32), and

Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.



[0080] In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

[0081] In one or more embodiments, xa5 may be 1, 2, 3, or 4.

[0082] In one or more embodiments, R201 to R204 and Q201 may each independently be selected from 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 benzofluorenyl group, a dibenzofluorenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and
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 benzofluorenyl group, a dibenzofluorenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl 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 amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with -F, 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 benzofluorenyl group, a dibenzofluorenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, -Si(Q31)(Q32)(Q33) and -N(Q31)(Q32), and
Q31 to Q33 may each independently be the same as described above.

[0083] In one or more embodiments, in Formula 201, at least one of R201 to R203 may each independently be selected from the group consisting of:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.



[0084] In one or more embodiments, in Formula 202, i) R201 and R202 may be linked (e.g., coupled) via a single bond, and/or ii) R203 and R204 may be linked (e.g., coupled) via a single bond.

[0085] In one or more embodiments, in Formula 202, at least one of R201 to R204 may be selected from the group consisting of:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.



[0086] The compound represented by Formula 201 may be represented by Formula 201A:



[0087] In some embodiments, the compound represented by Formula 201 may be further represented by Formula 201A(1), but embodiments of the present disclosure are not limited thereto:





[0088] In some embodiments, the compound represented by Formula 201 may be further represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:



[0089] In some embodiments, the compound represented by Formula 202 may be further represented by Formula 202A:



[0090] In some embodiments, the compound represented by Formula 202 may be further represented by Formula 202A-1:



[0091] In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,
L201 to L203, xa1 to xa3, xa5, and R202 to R204 may each independently be the same as described above,
R211 and R212 may each independently be the same as described in connection with R203, and
R213 to R217 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with -F, 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 benzofluorenyl group, a dibenzofluorenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

[0092] The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:



























[0093] The thickness of the hole transport region may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 7000 Å, about 100 Å to about 5000 Å, about 100 Å to about 3000 Å, or 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, the thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 7,000 Å, about 100 Å to about 5,000 Å, about 100 Å to about 3,000 Å or about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å or about 100 Å to about 500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, suitable or satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

[0094] The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer(e.g., by adjusting the optical resonance distance in the device to match the wavelength of light emitted from the emission layer), and the electron blocking layer may block or reduce the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials as described above.

P-dopant



[0095] The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

[0096] The charge-generation material may be, for example, a p-dopant.

[0097] In some embodiments, the p-dopant may have a lowest unoccupied molecular (LUMO) energy level of -3.5 eV or less.

[0098] The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

[0099] For example, the p-dopant may include at least one selected from the group consisting of:

a quinone derivative (such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));

a metal oxide (such as tungsten oxide or molybdenum oxide);

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments of the present disclosure are not limited thereto:





[0100] In Formula 221,
R221 to R223 may each independently be selected from 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 (e.g. C6-C32) aryl group, a substituted or unsubstituted C1-C60 (e.g. C1-C20) heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one of R221 to R223 has at least one substituent selected from a cyano group, -F, -CI, -Br, -I, a C1-C20 alkyl group substituted with -F, a C1-C20 alkyl group substituted with -CI, a C1-C20 alkyl group substituted with -Br, and a C1-C20 alkyl group substituted with -I.

Emission layer in organic layer 150



[0101] 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, or a blue emission layer, according to a sub-pixel (e.g., corresponding to a group of sub-pixels). In one or more embodiments, the emission layer may have a stacked structure including two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

[0102] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0103] An amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0104] The thickness of the emission layer may be about 100 Å to about 1,000 Å, for example, about 100 Å to about 800 Å, about 150 Å to about 800 Å, about 150 Å to about 700 Å, about 150 Å to about 650 Å, about 200 Å to about 600 Å or about 200 Å to about 400 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Host in emission layer



[0105] In one or more embodiments, the host may include a compound represented by Formula 301.

        Formula 301     [Ar301]xb11-(L301)xb1-R301]xb21.



[0106] In Formula 301,
Ar301 may be a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 may be 1, 2, or 3,
L301 may be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xb1 may be an integer of 0 to 5,
R301 may be selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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(Q301)(Q302)(Q303), -N(Q301)(Q302), -B(Q301)(Q302), -C(=O)(Q301), -S(=O)2(Q301), and - P(=O)(Q301)(Q302),
xb21 may be an integer from 1 to 5,
Q301 to Q303 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

[0107] For example, Ar301 may be a substituted or unsubstituted C6-C32 carbocyclic group or a substituted or unsubstituted C1-C12 heterocyclic group, but embodiments are not limited thereto.

[0108] In some embodiments, Ar301 in Formula 301 may be selected from the group consisting of:

a naphthalene 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, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and

a naphthalene 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, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one selected from deuterium, - F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, - Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and - P(=O)(Q31)(Q32), and

Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.



[0109] When xb11 in Formula 301 is two or more, two or more Ar301(s) may be linked (e.g., coupled) via a single bond.

[0110] In one or more embodiments, the compound represented by Formula 301 may be further represented by Formula 301-1 or 301-2:





[0111] In Formulae 301-1 and 301-2,
A301 to A304 may each independently be selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, and a dinaphthothiophene group,
X301 may be O, S, or N-[(L304)xb4-R304],
R311 to R314 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group -Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32),
xb22 and xb23 may each independently be 0, 1, or 2,
L301, xb1, R301, and Q31 to Q33 may each independently be the same as described above,
L302 to L304 may each independently be the same as described in connection with L301,
xb2 to xb4 may each independently be the same as described in connection with xb1, and
R302 to R304 may each independently be the same as described in connection with R301.

[0112] For example, L301 to L304 in Formulae 301, 301-1, and 301-2 may each independently be selected from: a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C1-C20 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, but embodiments are not limited thereto.

[0113] For example, in Formulae 301, 301-1, and 301-2, L301 to L304 may each independently be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -Si(Q31)(Q32)(Q33), -N(Q31)(Q32),-B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q31 to Q33 may each independently be the same as described above.



[0114] As another example, R301 to R304 in Formulae 301, 301-1, and 301-2 may each independently be selected from: deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 (e.g. C1-C10) alkyl group, a substituted or unsubstituted C2-C60 (e.g. C2-C10) alkenyl group, a substituted or unsubstituted C2-C60 (e.g. C2-C10) alkynyl group, a substituted or unsubstituted C1-C60 (e.g. C1-C10) 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-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q301)(Q302)(Q303), -N(Q301)(Q302),-B(Q301)(Q302), -C(=O)(Q301), -S(=O)2(Q301), and -P(=O)(Q301)(Q302), but embodiments are not limited thereto.

[0115] In some embodiments, in Formulae 301, 301-1, and 301-2, R301 to R304 may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -Si(Q31)(Q32)(Q33), -N(Q31)(Q32),-B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q31 to Q33 may each independently be the same as described above.



[0116] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may include a complex selected from a Be complex (for example, Compound H55), a Mg complex, and a Zn complex. For example, the host may be selected from a Be complex (for example, Compound H55), an Mg complex, and a Zn complex.

[0117] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:































[0118] In some embodiments, the host may include at least one selected from a silicon-containing compound (for example, BCPDS as used in the examples and/or the like) and a phosphine oxide-containing compound (for example, POPCPA as used in the examples and/or the like).

[0119] However, embodiments of the present disclosure are not limited thereto. In some embodiments, the host may include only one compound, or two or more different compounds (for example, BCPDS and/or POPCPA).

Phosphorescent dopant included in emission layer in organic layer 150



[0120] The phosphorescent dopant may include an organometallic compound represented by Formula 1.

Electron transport region in organic layer 150



[0121] The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

[0122] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.

[0123] For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the constituting layers in each structure are sequentially stacked on the emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.

[0124] The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

[0125] The term "π electron-depleted nitrogen-containing ring" as used herein may refer to a ring-forming moiety, and for example, may be a C1-C60 (e.g. a C1-C30) heterocyclic group including at least one *-N=*' moiety.

[0126] For example, the "π electron-depleted nitrogen-containing ring" may be i) a 5-membered to 7-membered heteromonocyclic group including at least one *-N=*' moiety, ii) a heteropolycyclic group including two or more condensed 5-membered to 7-membered heteromonocyclic groups, wherein each 5-membered to 7-membered heteromonocyclic group includes at least one *-N=*' moiety, or iii) a heteropolycyclic group in which at least one 5-membered to 7-membered heteromonocyclic group is condensed with at least one C5-C60 (e.g. a C5-C30) carbocyclic group, wherein each 5-membered to 7-membered heteromonocyclic group includes at least one *-N=*' moiety.

[0127] Non-limiting examples of the π electron-depleted nitrogen-containing ring may include an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine 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 phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, but embodiments of the present disclosure are not limited thereto.

[0128] For example, the electron transport region may include a compound represented by Formula 601:

        Formula 601     [Ar601]xe11-(L601)xe1-R601]xe21.



[0129] In Formula 601,
Ar601 may be a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xe11 may be 1, 2, or 3,
L601 may be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xe1 may be an integer from 0 to 5,
R601 may be selected from 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(Q601)(Q602)(Q603), -C(=O)(Q601), -S(=O)2(Q601), and -P(=O)(Q601)(Q602),
Q601 to Q603 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
xe21 may be an integer from 1 to 5.

[0130] In some embodiments, at least one Ar601 group and R601 group (among the total number of groups provided by xe11 and xe21, respectively) may include the π electron-depleted nitrogen-containing ring described above.

[0131] For example, Ar601 may be a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C20 heterocyclic group, but embodiments are not limited thereto.

[0132] In some embodiments, in Formula 601, ring Ar601 may be selected from the group consisting of:

a benzene group, a naphthalene 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, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine 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 phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene 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, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine 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 phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, -Si(Q31)(Q32)(Q33), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.



[0133] When xe11 in Formula 601 is two or more, two or more Ar601(s) may be linked (e.g., coupled) via a single bond.

[0134] In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.

[0135] In one or more embodiments, a compound represented by Formula 601 may be further represented by Formula 601-1:





[0136] In Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), and X616 may be N or C(R616), wherein at least one of X614 to X616 may be N,
L611 to L613 may each independently be the same as described in connection with L601,
xe611 to xe613 may each independently be the same as described in connection with xe1,
R611 to R613 may each independently be the same as described in connection with R601, and
R614 to R616 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0137] For example, L601 and L611 to L613 in Formulae 601 and 601-1 may each independently be selected from: a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C1-C20 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, but embodiments are not limited thereto.

[0138] In some embodiments, in Formulae 601 and 601-1, L601 and L611 to L613 may each independently be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, but embodiments of the present disclosure are not limited thereto.



[0139] In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.

[0140] For example, R601 and R611 to R613 in Formulae 601 and 601-1 may each independently be selected from: 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-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,-Si(Q601)(Q602)(Q603), -C(=O)(Q601), -S(=O)2(Q601), and -P(=O)(Q601)(Q602).

[0141] In one or more embodiments, in Formulae 601 and 601-1, R601 and R611 to R613 may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and

-S(=O)2(Q601) and -P(=O)(Q601)(Q602), and

Q601 and Q602 may each independently be the same as described above.



[0142] The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

























[0143] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:





[0144] In some embodiments, the electron transport region may include a phosphine oxide-containing compound (for example, TSPO1 as used in the examples and/or the like), but embodiments of the present disclosure are not limited thereto. In some embodiments, the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but embodiments of the present disclosure are not limited thereto.

[0145] The thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be about 20 Å to about 1,000 Å, for example, about 20 Å to about 700 Å, about 20 Å to about 500 Å, about 20 Å to about 400, about 30 Å to about 400 Å or about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and/or the electron control layer are within these ranges, the electron blocking layer may have excellent electron blocking characteristics and/or electron control characteristics without a substantial increase in driving voltage.

[0146] The th ickness of the electron transport layer may be about 100 A to about 1,000 Å, for example, about 100 Å to about 700 Å, about 100 Å to about 600 Å. about 150 Å to about 600 Å, about 150 Å to about 500 Å or about 250 Å to about 350 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have suitable or satisfactory electron transport characteristics without a substantial increase in driving voltage.

[0147] The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

[0148] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion, and the alkaline earth-metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

[0149] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/or Compound ET-D2:



[0150] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

[0151] The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

[0152] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

[0153] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In some embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure are not limited thereto.

[0154] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0155] The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

[0156] The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.

[0157] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, and/or K2O), and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI). In some embodiments, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but embodiments of the present disclosure are not limited thereto.

[0158] The alkaline earth-metal compound may be selected from alkaline earth-metal oxides (such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), and/or BaxCa1-xO (0<x<1)). In some embodiments, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.

[0159] The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In some embodiments, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but embodiments of the present disclosure are not limited thereto.

[0160] The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an alkali metal ion, alkaline earth-metal ion, and/or a rare earth metal ion's described above, and a ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth-metal complex, and/or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

[0161] The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or combination thereof, that material may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

[0162] The thickness of the electron injection layer may be about 1 Å to about 100 Å, for example, about 1 Å to about 95 Å, about 2 Å to about 95 Å, about 3 Å to about 90 Å or about 5 Å to about 15 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have suitable or satisfactory electron injection characteristics without a substantial increase in driving voltage.

Second electrode 190



[0163] The second electrode 190 may be on the organic layer 150 having the above-described structure. The second electrode 190 may be a cathode that is an electron injection electrode, and in this regard, the material for forming the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, or a combination thereof, each having a relatively low work function.

[0164] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), indium titanium oxide (ITO), and indium zinc oxide (IZO), but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0165] The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.

[0166] The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a particular region or position using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.

[0167] When each layer is formed by vacuum deposition, the deposition conditions may be selected depending on the compound used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. 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 (wherein 1 torr = 133.322 Pa), and a deposition rate of about 0.01 Å/sec to about 100 Å/sec.

[0168] When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm (wherein 1 rpm = 1/60 Hz) and at a heat treatment temperature of about 80 °C to about 200 °C depending on the material to be included in a layer to be formed, and the structure of the layer to be formed.

General definition of some of the substituents



[0169] The term "C1-C60 alkyl group" as used herein may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof may include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term "C1-C60 alkylene group" as used herein may refer to a divalent group having substantially the same structure as the C1-C60 alkyl group. Corresponding definitions apply to other ranges given for the number of carbon atoms in an alkyl/alkylene group.

[0170] The term "C2-C60 alkenyl group" as used herein may refer to a hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminus of the C2-C60 alkyl group, and non-limiting examples thereof may include an ethenyl group, a propenyl group, and a butenyl group. The term "C2-C60 alkenylene group" as used herein may refer to a divalent group having substantially the same structure as the C2-C60 alkenyl group. Corresponding definitions apply to other ranges given for the number of carbon atoms in an alkenyl/alkenylene group.

[0171] The term "C2-C60 alkynyl group" as used herein may refer to a hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminus of the C2-C60 alkyl group, and non-limiting examples thereof may include an ethynyl group and a propynyl group. The term "C2-C60 alkynylene group" as used herein may refer to a divalent group having substantially the same structure as the C2-C60 alkynyl group. Corresponding definitions apply to other ranges given for the number of carbon atoms in an alkynyl/alkynylene group.

[0172] The term "C1-C60 alkoxy group" as used herein may refer to a monovalent group represented by -OA101 (wherein A101 is a C1-C60 alkyl group), and non-limiting examples thereof may include a methoxy group, an ethoxy group, and an isopropyloxy group. Corresponding definitions apply to other ranges given for the number of carbon atoms in an alkoxy group.

[0173] The term "C3-C10 cycloalkyl group" as used herein may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term "C3-C10 cycloalkylene group" as used herein may refer to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.

[0174] The term "C1-C10 heterocycloalkyl group" as used herein may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term "C1-C10 heterocycloalkylene group" as used herein may refer to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.

[0175] The term "C3-C10 cycloalkenyl group" as used herein may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity (e.g., the C3-C10 cycloalkenyl group is not aromatic), and non-limiting examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term "C3-C10 cycloalkenylene group" as used herein may refer to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.

[0176] The term "C1-C10 heterocycloalkenyl group" as used herein may refer to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term "C1-C10 heterocycloalkenylene group" as used herein may refer to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.

[0177] The term "C6-C60 aryl group" as used herein may refer to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C6-C60 arylene group" as used herein may refer to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group may include 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 include two or more rings, the rings may be fused to each other. Corresponding definitions apply to other ranges given for the number of carbon atoms in an aryl/arylene group.

[0178] The term "C1-C60 heteroaryl group" as used herein may refer to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term "C1-C60 heteroarylene group" as used herein may refer to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group may 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 include two or more rings, the rings may be condensed with (e.g., fused to) each other. Corresponding definitions apply to other ranges given for the number of carbon atoms in an heteroaryl/heteroarylene group.

[0179] The term "C6-C60 aryloxy group" as used herein may refer to -OA102 (wherein A102 is a C6-C60 aryl group), and the term "C6-C60 arylthio group" as used herein may refer to -SA103 (wherein A103 is a C6-C60 aryl group). Corresponding definitions apply to other ranges given for the number of carbon atoms in an aryloxy group and an arylthio group. The term "C1-C60 heteroaryloxy group" as used herein may refer to -OA104 (wherein A104 is a C1-C60 heteroaryl group), and the term "C1-C60 heteroarylthio group" as used herein may refer to -SA105 (wherein A105 is a C1-C60 heteroaryl group).

[0180] The term "monovalent non-aromatic condensed polycyclic group" as used herein may refer to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed with each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., the entire molecule is not aromatic). A non-limiting example of the monovalent non-aromatic condensed polycyclic group may be a fluorenyl group. The term "divalent non-aromatic condensed polycyclic group" as used herein may refer to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

[0181] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and no aromaticity in its entire molecular structure (e.g., the entire molecule is not aromatic). A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group may be a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0182] The term "C4-C60 carbocyclic group" or "C5-C60 carbocyclic group" as used herein may refer to a monocyclic or polycyclic group having 4 to 60 or 5 to 60 carbon atoms in which a ring-forming atom is a carbon atom only. The C4-C60 or C5-C60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C4-C60 or C5-C60 carbocyclic group may be a ring (such as benzene group), a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In one or more embodiments, depending on the number of substituents connected to the C4-C60 or C5-C60 carbocyclic group, the C4-C60 or C5-C60 carbocyclic group may be a trivalent group or a quadrivalent group. Corresponding definitions apply to other ranges given for the number of carbon atoms in a carbocyclic group.

[0183] The term "C2-C60 heterocyclic group" or "C1-C60 heterocyclic group" as used herein may refer to a group having substantially the same structure as the C4-C60 or C5-C60 carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms may be in a range of 1 to 60 or 2 to 60). Corresponding definitions apply to other ranges given for the number of carbon atoms in a heterocyclic group.

[0184] At least one substituent of the substituted C4-C60 carbocyclic group, the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C2-C60 heterocyclic group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from the group consisting of:

deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, and a C1-C60 (e.g. C1-C20) alkoxy group;

a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, and a C1-C60 (e.g. 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 amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q11)(Q12)(Q13),-N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11), -S(=O)2(Q11), and -P(=O)(Q11)(Q12);

a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) 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, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C6-C60 (e.g. C6-C30) aryloxy group, a C6-C60 (e.g. C6-C30) arylthio group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q21)(Q22)(Q23), -N(Q21)(Q22),-B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21), and -P(=O)(Q21)(Q22); and

-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and -P(=O)(Q31)(Q32), and

Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 (e.g. C1-C20) alkyl group, a C2-C60 (e.g. C2-C20) alkenyl group, a C2-C60 (e.g. C2-C20) alkynyl group, a C1-C60 (e.g. C1-C20) 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 (e.g. C6-C30) aryl group, a C1-C60 (e.g. C1-C20) heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 (e.g. C1-C20) alkyl group substituted with at least one selected from deuterium, -F, and a cyano group; a C6-C60 (e.g. C6-C30) aryl group substituted with at least one selected from deuterium, -F, and a cyano group; a biphenyl group, and a terphenyl group.



[0185] The term "Ph" as used herein may represent a phenyl group, the term "Me" as used herein may represent a methyl group, the term "Et" as used herein may represent an ethyl group, the term "ter-Bu" or "But," as used herein, may represent a tert-butyl group, and the term "OMe" as used herein may represent a methoxy group.

[0186] The term "biphenyl group" as used herein may refer to a "phenyl group substituted with a phenyl group". A "biphenyl group" is an example of "a substituted phenyl group" including a "C6-C60 aryl group" (specifically, a phenyl group) as a substituent.

[0187] The term "terphenyl group" as used herein may refer to a "phenyl group substituted with a biphenyl group". A "terphenyl group" is an example of a "phenyl group" including a "C6-C60 aryl group substituted with a C6-C60 aryl group" (specifically, a phenyl group substituted with a phenyl group) as a substituent.

[0188] * and *' used herein, unless defined otherwise, may each refer to a binding site to a neighboring atom in a corresponding formula.

[0189] Hereinafter, a compound according to embodiments of the present disclosure and an organic light-emitting device according to embodiments of the present disclosure will be described in more detail with reference to Synthesis Examples and Examples. The expression "B was used instead of A" used in describing the Synthesis Examples means that an identical number of molar equivalents of A was used in place of molar equivalents of B.

Synthesis Examples


Synthesis Example 1: Synthesis of Compound 1



[0190] 


1) Synthesis of Intermediate [1-A]



[0191] 2-methoxy-9H-carbazole (1.0 eq), 2-iodopyridine (1.2 eq), Pd2(dba)3 (0.05 eq), SPhos (0.10 eq), and K2CO3 (1.0 eq) were dissolved in toluene (0.1 M) and stirred at a temperature of 120 °C for 18 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried over magnesium sulfate and concentrated, and column chromatography was performed thereon to obtain Intermediate [1-A] (yield: 91 %).

2) Synthesis of Intermediate [1-B]



[0192] Compound [1-A] (1.0 eq) was dissolved in dichloromethane (0.1 M) and stirred at a temperature of -78 °C, and boron tribromide solution (1.0 M in hexane, 2.0 eq) was slowly added thereto and stirred for 2 hours. The reaction mixture was neutralized using sodium bicarbonate aqueous solution, and an organic layer was extracted therefrom three times using ethyl acetate and water. The extracted organic layer was dried over magnesium sulfate and concentrated to obtain Intermediate [1-B] (yield: 64%).

3) Synthesis of Intermediate [1-C]



[0193] 2-bromo-4H-benzo[def]carbazole (1.0 eq), 2-iodopyridine (1.2 eq), Pd2(dba)3 (0.05 eq), SPhos (0.10 eq), and K2CO3 (1.0 eq) were dissolved in toluene (0.1 M) and stirred at a temperature of 120 °C for 18 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried over magnesium sulfate and concentrated, and column chromatography was performed thereon to obtain Intermediate [1-C] (yield: 93 %).

4) Synthesis of Intermediate [1-D]



[0194] Compound [1-B] (1.0 eq), Compound [1-C] (1.2 eq), Cul (0.02 eq), K2CO3 (2.0 eq), and L-Proline (0.04 eq) were dissolved in dimethyl sulfoxide (0.1M) and stirred at a temperature of 160 °C for 48 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried over magnesium sulfate and concentrated, and column chromatography was performed thereon to obtain Intermediate [1-D] (yield: 44 %).

5) Synthesis of Compound 1



[0195] Compound [1-D] (1.0 eq), potassium tetrachloroplatinate (K2PtCl4) (1.1 eq), and tetrabutylammonium bromide (0.1 eq) were dissolved in acetic acid (0.1M) and stirred at a temperature of 120 °C for 72 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried over magnesium sulfate and concentrated, and column chromatography was performed thereon to obtain Compound 1 (yield: 31 %).

Synthesis Example 2: Synthesis of Compound 11



[0196] 


1) Synthesis of Intermediate [11-A]



[0197] 3-bromo iodobenzene (1.0 eq), 1H-imidazole (1.2 eq), Cul (0.02 eq), K2CO3 (2.0 eq), and L-Proline (0.04 eq) were dissolved in dimethylsulfonate (0.1M) and stirred at a temperature of 130 °C for 12 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried over magnesium sulfate and concentrated, and column chromatography was performed thereon to obtain Intermediate [11-A] (yield: 65 %).

2) Synthesis of Intermediate [11-B]



[0198] Intermediate [11-B] (yield: 32 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-D], except that Intermediate [11-A] was used instead of Intermediate [1-C], and Intermediate [41-B] as described in Synthesis Example 5 was used instead of Intermediate [1-B].

3) Synthesis of Intermediate [11-C]



[0199] Compound [11-B] (1.0 eq) and iodomethane (1.5 eq) were dissolved in tetrahydrofuran (0.1 M) and stirred at a temperature of 70 °C for 12 hours. After the reaction mixture was cooled to room temperature, a solvent was removed therefrom. The resultant mixture was filtered and washed using diethyl ether to obtain Intermediate [11-C] (yield: 85 %).

4) Synthesis of Compound 11



[0200] Compound [11-C] (1.0 eq), dichloro(1,5-cyclooctadienyl) platinum(II) (1.05 eq), and sodium acetate (3.0 eq) were dissolved in tetrahydrofuran (0.1 M) and stirred at a temperature of 120 °C in a nitrogen atmosphere for 72 hours. The reaction mixture was cooled to room temperature and depressurized to remove a solvent therefrom. The concentrated reaction mixture was dissolved in dichloromethane, and a remaining precipitate was filtered. A filtrate was purified by column chromatography to obtain Compound 11 (yield: 35 %).

Synthesis Example 3: Synthesis of Compound 21



[0201] 


1) Synthesis of Intermediate [21-A]



[0202] Intermediate [21-A] (yield: 57 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [11-A], except that benzimidazole was used instead of 1H-imidazole.

2) Synthesis of Intermediate [21-B]



[0203] Intermediate [21-B] (yield: 31 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-D], except that Intermediate [21-A] was used instead of Intermediate [1-C], and Intermediate [41-B] as described in Synthesis Example 5 was used instead of Intermediate [1-B].

3) Synthesis of Intermediate [21-C]



[0204] Intermediate [21-C] (yield: 84 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [11-C], except that Intermediate [21-B] was used instead of Intermediate [11-B].

4) Synthesis of Compound 21



[0205] Synthesis 21 (yield: 28 %) was synthesized in substantially the same manner as in the Synthesis of Compound 11, except that Intermediate [21-C] was used instead of Intermediate [11-C].

Synthesis Example 4: Synthesis of Compound 31



[0206] 


1) Synthesis of Intermediate [31-A]



[0207] Intermediate [31-A] (yield: 86 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-A], except that 3-methoxy-5H-pyrrolo[3,2-b:4,5-b']dipyridine was used instead of 2-methoxy-9H-carbazole.

2) Synthesis of Intermediate [31-B]



[0208] Intermediate [31-B] (yield: 68 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-B], except that Intermediate [31-A] was used instead of Intermediate [1-A].

3) Synthesis of Intermediate [31-C]



[0209] Intermediate [31-C] (yield: 24 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-D], except that Intermediate [31-B] was used instead of Intermediate [1-B].

4) Synthesis of Compound 31



[0210] Compound 31 (yield: 37 %) was synthesized in substantially the same manner as in the Synthesis of Compound 1, except that Intermediate [31-C] was used instead of Intermediate [1-D].

Synthesis Example 5: Synthesis of Compound 41



[0211] 


1) Synthesis of Intermediate [41-A]



[0212] Intermediate [41-A] (yield: 88 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-A], except that 2-methoxy-4H-benzo[def]carbazole was used instead of 2-methoxy-9H-carbazole.

2) Synthesis of Intermediate [41-B]



[0213] Intermediate [41-B] (yield: 66 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-B], except that Intermediate [41-A] was used instead of Intermediate [1-A].

3) Synthesis of Intermediate [41-C]



[0214] Intermediate [41-C] (yield: 31 %) was synthesized in substantially the same manner as in the Synthesis of Intermediate [1-D], except that Intermediate [41-B] was used instead of Intermediate [1-B].

4) Synthesis of Compound 41



[0215] Compound 41 (yield: 33 %) was synthesized in substantially the same manner as in the Synthesis of Compound 1, except that Intermediate [41-C] was used instead of Intermediate [1-D].

Examples


Example 1



[0216] As an anode, a Corning 15 Ω/cm2 (1,200 Å) ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, sonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus. Compound 2-TNATA was vacuum-deposited on the ITO glass substrate to form a hole injection layer having a thickness of 600 Å, and 4,4'-bis[N-(1-naphthyl)-N-phenyl aminobiphenyl (NPB) (hole transport compound) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å. 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP) (host) and Compound 1 (dopant) were codeposited on the hole transport layer in a ratio of 10% dopant (e.g., and 90% host) to form a green phosphorescent emission layer having a thickness of 300 Å. Then, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å. Then, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å. LiF, which is an alkali metal halide, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode electrode having a thickness of 3,000 Å, thereby forming a LiF/AI electrode. In this manner, an organic light-emitting device was manufactured.




Examples 2 to 5 and Comparative Examples 1 to 4



[0217] Additional organic light-emitting devices were manufactured in each the same manner as in Example 1, except that the Compounds shown in Table 1 were used instead of Compound 1 as a dopant in forming each an emission layer.

Evaluation Example 1



[0218] The driving voltage, current density, luminance, luminescent efficiency, and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Examples 1 to 4 were measured using a Keithley SMU 236 and a luminance meter PR650 (Tektronix, Inc., Beaverton, OR), and results thereof are shown in Table 1.
Table 1
 Emission layerDriving voltage (V)Current density (mA/cm2)Luminance (cd/m2)Efficiency (cd/A)Emission colorEmission wavelength (nm)Lifespan (RT80%@ J=40 mA/cm2) (hr)
Example 1 Compound 1 5.11 50 4125 8.25 Green 532 360
Example 2 Compound 11 5.17 50 4025 8.05 Green 529 327
Example 3 Compound 21 5.15 50 4033 8.07 Green 535 348
Example 4 Compound 31 5.20 50 4024 8.05 Green 533 351
Example 5 Compound 41 5.13 50 4055 8.11 Red 591 369
Comparative Example 1 Ir(ppy)3 6.74 50 3870 7.74 Green 516 278
Comparative Example 2 Compound 46 6.68 50 3790 7.58 Green 515 194
Comparative Example 3 Compound 47 6.72 50 3535 7.07 Green 537 307
Comparative Example 4 Compound 48 6.81 50 3325 6.65 Red 592 312




[0219] Referring to Table 1, it is confirmed that the organic light-emitting devices of Examples 1 to 5 have a low driving voltage, high luminance, high luminescent efficiency, and a long lifespan, compared with the organic light-emitting devices of Comparative Examples 1 to 4.

[0220] An organic light-emitting device including the organometallic compound according to embodiments of the present disclosure may have a low driving voltage, high efficiency, high luminance, and a long lifespan.

[0221] As used herein, the terms "use", "using", and "used" may be considered synonymous with the terms "utilize", "utilizing", and "utilized", respectively. Further, the use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure".

[0222] As used herein, the terms "substantially", "about", and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.

[0223] Also, any numerical range recited herein is intended to include all subranges of the same numerical precision subsumed within the recited range. For example, a range of "1.0 to 10.0" is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein.

[0224] 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.

[0225] While one or more embodiments have been described with reference to the drawing, 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 as defined by the following claims.


Claims

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,

M11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

A11 to A16 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,

Y11 to Y14 are each independently N or C,

T11 to T14 are each independently selected from a single bond, *-O-*', and *-S-*',

L11 to L13 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-C(R17)=C(R18)-*', *-C(=O)-*', *-C(=S)-*', *-C=C-*', *-B(R17)-*', *-N(R17)-*', *-P(R17)-*', *-Si(R17)(R18)-*', *-P(R17)(R18)-*', and *-Ge(R17)(R18)-*',

a11 to a13 are each independently selected from 0, 1, 2, and 3,

when a11 is zero, A11 and A12 are not linked to each other,

when a12 is zero, A12 and A13 are not linked to each other,

when a13 is zero, A13 and A14 are not linked to each other,

R11 to R18 are each independently selected from hydrogen, deuterium, -F, -Cl, - Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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),-B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1),-P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2),

R16 and R11, or R17 and R14 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,

R14 and R15, or R15 and R16 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,

R17 and R11, R17 and R12, or R17 and R13 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,

b11 to b16 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,

Q1 to Q3 are each independently selected from hydrogen, deuterium, -F, -Cl,-Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,

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

at least one substituent of the substituted C4-C60 carbocyclic group, the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C2-C60 heterocyclic group, 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:

deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, -F, -Cl,-Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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(Q11)(Q12)(Q13), -N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11),-S(=O)2(Q11), and -P(=O)(Q11)(Q12);

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, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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(Q21)(Q22), -B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21), and -P(=O)(Q21)(Q22); and

-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), and-P(=O)(Q31)(Q32), and

Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, -F, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, -F, and a cyano group; a biphenyl group, and a terphenyl group.


 
2. An organometallic compound according to claim 1, wherein: M11 is selected from Pt, Pd, Cu, Ag, and Au.
 
3. An organometallic compound according to claim 1 or claim 2, wherein:
A11 to A16 are each independently selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indeno pyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indeno pyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.
 
4. An organometallic compound according to any one of claims 1 to 3, wherein:
A11 to A13 are each independently represented by one of Formulae 2-1 to 2-43:













wherein, in Formulae 2-1 to 2-43,

X21 to X23 are each independently selected from C(R24) and C-*, provided that at least two of X21 to X23 are each C-*,

X24 is N-*, and X25 and X26 are each independently selected from C(R24) and C-*, provided that at least one of X25 and X26 is C-*,

X27 and X28 are each independently selected from N, N(R25), and N-*, and X29 is selected from C(R24) and C-*, wherein i) at least one of X27 and X28 is N-* and X29 is C-*; or ii) X27 and X28 are each N-* and X29 is C(R24),

R21 to R24 are each independently the same as described in connection with R11 in Formula 1,

b21 is selected from 1, 2, and 3,

b22 is selected from 1, 2, 3, 4, and 5,

b23 is selected from 1, 2, 3, and 4,

b24 is selected from 1 and 2, and

* indicates a binding site to a neighboring atom.


 
5. An organometallic compound according to any one of claims 1 to 4, wherein:
A14 to A16 are each independently represented by one of Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4,

X21 to X23 are each independently selected from C(R24) and C-*, provided that at least two of X21 to X23 are each C-*,

X24 is N-*, and X25 and X26 are each independently selected from C(R24) and C-*, provided that at least one of X25 and X26 is C-*,

R21 to R22 are each independently the same as described in connection with R11 in Formula 1,

b21 is selected from 1, 2, and 3, and

* indicates a binding site to a neighboring atom.


 
6. An organometallic compound according to any one of claims 1 to 5, wherein: in Formula 1,
a moiety represented by

is a moiety represented by one of Formulae 1-1 to 1-64:































wherein, in Formulae 1-1 to 1-64,

Y14 is the same as described in claim 1, and

*, *', and *" each indicate a binding site to a neighboring atom.


 
7. An organometallic compound according to any one of claims 1 to 6, wherein:

Y11, Y12, and Y13 are each C, and Y14 is N;

Y11, Y12, and Y14 are each C, and Y13 is N;

Y11, Y13, and Y14 are each C, and Y12 is N;

Y12, Y13, and Y14 are each C, and Y11 is N;

Y11 and Y14 are each C, and Y12 and Y13 are each N;

Y11 and Y14 are each N, and Y12 and Y13 are each C;

Y11 and Y12 are each C, and Y13 and Y14 are each N;

Y11 and Y12 are each N, and Y13 and Y14 are each C;

Y11 and Y13 are each C, and Y12 and Y14 are each N; or

Y11 and Y13 are each N, and Y12 and Y14 are each C.


 
8. An organometallic compound according to any one of claims 1 to 7, wherein:

T11 to T14 are each a single bond;

T11 is selected from *-O-*' and *-S-*', and T12 to T14 are each a single bond;

T12 is selected from *-O-*' and *-S-*', and T11, T13, and T14 are each a single bond;

T13 is selected from *-O-*' and *-S-*', and T11, T12, and T14 are each a single bond; or

T14 is selected from *-O-*' and *-S-*', and T11, T12, and T13 are each a single bond.


 
9. An organometallic compound according to any one of claims 1 to 8, wherein:
L11 to L13 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R17)(R18)-*, *-C(R17)=*', *=C(R17)-*', *-B(R17)-*', *-N(R17)-*', *-Si(R17)(R18)-*', and *-P(R17)(R18)-*'.
 
10. An organometallic compound according to any one of claims 1 to 9, wherein:

L11 is *-N(R17)-*', *-C(R17)(R18)-*', or *-Si(R17)(R18)-*', and R17 and R12 are linked to form a substituted or unsubstituted C1-C60 heterocyclic group, or

L12 is *-N(R17)-*', *-C(R17)(R18)-*', or *-Si(R17)(R18)-*', and R17 and R13 are linked to form a substituted or unsubstituted C1-C60 heterocyclic group.


 
11. An organometallic compound according to any one of claims 1 to 10, wherein:

a11 is 0, and a12 and a13 are each independently selected from 1, 2, and 3;

a12 is 0, and a11 and a13 are each independently selected from 1, 2, and 3; or

a13 is 0, and a11 and a12 are each independently selected from 1, 2, and 3.


 
12. An organometallic compound according to any one of claims 1 to 11, wherein: a11 is 0.
 
13. An organometallic compound according to any one of claims 1 to 12, wherein:
R11 to R18 are each independently selected from the group consisting of:

hydrogen, deuterium, -F, -Cl, -Br, -I, 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, -F, -Cl, -Br, -I, a cyano group, a phenyl group, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl 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 indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, an indolocarbazolyl group, - Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)(Q31), -S(=O)2(Q31),-P(=O)(Q31)(Q32), and -P(=S)(Q31)(Q32); and

-Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1),-S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), and

Q1 to Q3 and Q31 to Q33 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, -F, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, -F, and a cyano group, a biphenyl group, and a terphenyl group.


 
14. An organometallic compound according to any one of claims 1 to 13, wherein:
the organometallic compound is represented by Formula 3-1 or 3-2:





wherein, in Formulae 3-1 and 3-2,

M11, A11 to A13, Y11 to Y14, T11 to T14, L11 to L13, a11 to a13, R11 to R13, and b11 to b13 are the same as described in any one of claims 1 to 13,

Y31 to Y37 are each independently N or C,

Y41 to Y47 are each independently N or C,

R31 to R33 are each independently the same as described in connection with R14 in claim 1,

R41 to R43 are each independently the same as described in connection with R13 in claim 1,

b31, b32, b41, and b42 are each independently 1 or 2, and

b33 and b43 are each independently 1, 2, or 3.


 
15. An organometallic compound according to claim 1, wherein:
the organometallic compound represented by Formula 1 is selected from Compounds 1 to 45:
























 
16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

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

wherein the organic layer comprises an emission layer and an organometallic compound according to any one of claims 1 to 15.


 
17. An organic light-emitting device according to claim 16, wherein:

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

the hole transport region comprises at least one layer selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and

the electron transport region comprises at least one layer selected from a hole blocking layer, an electron transport layer, and an electron injection layer.


 
18. An organic light-emitting device according to claim 17, wherein: the emission layer comprises the organometallic compound.
 
19. An organic light-emitting device according to claim 18, wherein:

the emission layer further comprises a host, and

the host comprises a carbazole-containing compound.


 
20. An organic light-emitting device according to any one of claims 17 to 19, wherein:

the electron transport region comprises the hole blocking layer, and

the hole blocking layer comprises a phosphine oxide-containing compound or a silyl-containing compound.


 


Ansprüche

1. Organometallische Verbindung, dargestellt von Formel 1:

wobei in Formel 1

M11 ausgewählt ist aus Platin (Pt), Palladium (Pd), Kupfer (Cu), Silber (Ag), Gold (Au), Rhodium (Rh), Iridium (Ir), Ruthenium (Ru), Osmium (Os), Titan (Ti), Zirconium (Zr), Hafnium (Hf), Europium (Eu), Terbium (Tb) und Thulium (Tm),

A11 bis A16 jeweils unabhängig ausgewählt sind aus einer carbocyclischen C5-C60-Gruppe und einer heterocyclischen C1-C60-Gruppe,

Y11 bis Y14 jeweils unabhängig N oder C sind,

T11 bis T14 jeweils unabhängig ausgewählt sind aus einer Einzelbindung, *-O-*' und *-S-*',

L11 bis L13 jeweils unabhängig ausgewählt sind aus einer Einzelbindung, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-C(R17)=C(R18)-*', *-C(=O)-*', *-C(=S)-*', *-C=C-*', *-B(R17)-*', *-N(R17)-*', *-P(R17)-*', *-Si(R17)(R18)-*', *-P(R17)(R18)-*' und *-Ge(R17)(R18)-*',

a11 bis a13 jeweils unabhängig ausgewählt sind aus 0, 1, 2 und 3,

wenn a11 null ist, A11 und A12 nicht miteinander verknüpft sind,

wenn a12 null ist, A12 und A13 nicht miteinander verknüpft sind ,

wenn a13 null ist, A13 und A14 nicht miteinander verknüpft sind,

R11 bis R18 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, - Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 C1-C60-Heteroaryloxygruppe, einer substituierten oder unsubstituierten C1-C60-Heteroarylthiogruppe, einer substituierten oder unsubstituierten einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer substituierten oder unsubstituierten einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2),-P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) und -P(=S)(Q1)(Q2),

R16 und R11 oder R17 und R14 gegebenenfalls verknüpft sind, um eine substituierte oder unsubstituierte carbocyclische C5-C60-Gruppe oder eine substituierte oder unsubstituierte heterocyclische C1-C60-Gruppe zu bilden,

R14 und R15 oder R15 und R16 gegebenenfalls verknüpft sind, um eine substituierte oder unsubstituierte carbocyclische C5-C60-Gruppe oder eine substituierte oder unsubstituierte heterocyclische C1-C60-Gruppe zu bilden,

R17 und R11, R17 und R12 oder R17 und R13 gegebenenfalls verknüpft sind, um eine substituierte oder unsubstituierte carbocyclische C5-C60-Gruppe oder eine substituierte oder unsubstituierte heterocyclische C1-C60-Gruppe zu bilden,

b11 bis b16 jeweils unabhängig ausgewählt sind aus 1, 2, 3, 4, 5, 6, 7 und 8,

Q1 bis Q3 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, einer Biphenylgruppe und einer Terphenylgruppe,

* und *' jeweils eine Bindungsstelle zu einem benachbarten Atom angeben,

mindestens ein Substituent der substituierten carbocyclischen C4-C60-Gruppe, der substituierten carbocyclischen C5-C60-Gruppe, der substituierten heterocyclischen C1-C60-Gruppe, der substituierten heterocyclischen C2-C60-Gruppe, der substituierten C1-C60-Alkylgruppe, der substituierten C2-C60-Alkenylgruppe, der substituierten C2-C60-Alkinylgruppe, 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 C1-C60-Heteroaryloxygruppe, der substituierten C1-C60-Heteroarylthiogruppe, der substituierten einwertigen nichtaromatischen kondensierten polycyclischen Gruppe und der substituierten einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe ausgewählt ist aus der Gruppe bestehend aus:

Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazonogruppe, 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 einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, - Si(Q11)(Q12)(Q13), -N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11), -S(=O)2(Q11) und-P(=O)(Q11)(Q12);

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 einwertigen nichtaromatischen kondensierten polycyclischen Gruppe und einer einwertigen nichtaromatischen kondensierten heteropolycyclischen 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 einwertigen nichtaromatischen kondensierten polycyclischen Gruppe und einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, - Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, - Si(Q21)(Q22)(Q23), -N(Q21)(Q22), -B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21) und-P(=O)(Q21)(Q22); und
-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31) und - P(=O)(Q31)(Q32), und

Q1 bis Q3, Q11 bis Q13, Q21 bis Q23 und Q31 bis Q33 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 C1-C60-Heteroarylgruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, einer C1-C60-Alkylgruppe, substituiert durch mindestens eines ausgewählt aus Deuterium, -F, und einer Cyanogruppe, einer C6-C60-Arylgruppe, substituiert durch mindestens eines ausgewählt aus Deuterium, - F und einer Cyanogruppe; einer Biphenylgruppe und einer Terphenylgruppe.


 
2. Organometallische Verbindung nach Anspruch 1, wobei: M11 ausgewählt ist aus Pt, Pd, Cu, Ag und Au.
 
3. Organometallische Verbindung nach Anspruch 1 oder Anspruch 2, wobei:
A11 bis A16 jeweils unabhängig ausgewählt sind aus einer Benzolgruppe, einer Naphthalingruppe, einer Anthracengruppe, einer Phenanthrengruppe, einer Triphenylengruppe, einer Pyrengruppe, einer Chrysengruppe, einer Cyclopentadiengruppe, einer 1,2,3,4-Tetrahydronaphthalingruppe, einer Furangruppe, einer Thiophengruppe, einer Silolgruppe, einer Indengruppe, einer Fluorengruppe, einer Indolgruppe, einer Carbazolgruppe, einer Benzofurangruppe, einer Dibenzofurangruppe, einer Benzothiophengruppe, einer Dibenzothiophengruppe, einer Benzosilolgruppe, einer Dibenzosilolgruppe, einer Indenopyridingruppe, einer Indolopyridingruppe, einer Benzofuropyridingruppe, einer Benzothienopyridingruppe, einer Benzosilolopyridingruppe, einer Indenopyrimidingruppe, einer Indolopyrimidingruppe, einer Benzofuropyrimidingruppe, einer Benzothienopyrimidingruppe, einer Benzosilolopyrimidingruppe, einer Dihydropyridingruppe, einer Pyridingruppe, einer Pyrimidingruppe, einer Pyrazingruppe, einer Pyridazingruppe, einer Triazingruppe, einer Chinolingruppe, einer Isochinolingruppe, einer Chinoxalingruppe, einer Chinazolingruppe, einer Phenanthrolingruppe, einer Pyrrolgruppe, einer Pyrazolgruppe, einer Imidazolgruppe, einer 2,3-Dihydroimidazolgruppe, einer Triazolgruppe, einer 2,3-Dihydrotriazolgruppe, einer Oxazolgruppe, einer Isoxazolgruppe, einer Thiazolgruppe, einer Isothiazolgruppe, einer Oxadiazolgruppe, einer Thiadiazolgruppe, einer Benzopyrazolgruppe, einer Benzimidazolgruppe, einer 2,3-Dihydrobenzimidazolgruppe, einer Imidazopyridingruppe, einer 2,3-Dihydroimidazopyridingruppe, einer Imidazopyrimidingruppe, einer 2,3-Dihydroimidazopyrimidingruppe, einer Imidazopyrazingruppe, einer 2,3-Dihydroimidazopyrazingruppe, einer Benzoxazolgruppe, einer Benzothiazolgruppe, einer Benzoxadiazolgruppe, einer Benzothiadiazolgruppe, einer 5,6,7,8-Tetrahydroisochinolingruppe und einer 5,6,7,8-Tetrahydrochinolingruppe.
 
4. Organometallische Verbindung nach einem der Ansprüche 1 bis 3, wobei:
A11 bis A13 jeweils unabhängig von einer der Formeln 2-1 bis 2-43 dargestellt werden:













wobei in den Formeln 2-1 bis 2-43

X21 bis X23 jeweils unabhängig ausgewählt sind aus C(R24) und C-*, mit der Maßgabe, dass mindestens zwei von X21 bis X23 jeweils C-* sind,

X24 N-* ist und X25 und X26 jeweils unabhängig ausgewählt sind aus C(R24) und C-*, mit der Maßgabe, dass mindestens eines von X25 und X26 C-* ist,

X27 und X28 jeweils unabhängig ausgewählt sind aus N, N(R25) und N-*, und X29 ausgewählt ist aus C(R24) und C-*, wobei i) mindestens eines von X27 und X28 N-* ist und X29 C-* ist; oder ii) X27 und X28 jeweils N-* sind und X29 C(R24) ist,

R21 bis R24 jeweils unabhängig dieselben wie im Zusammenhang mit R11 in Formel 1 beschrieben sind,

b21 ausgewählt ist aus 1, 2 und 3,

b22 ausgewählt ist aus 1, 2, 3, 4 und 5,

b23 ausgewählt ist aus 1, 2, 3 und 4,

b24 ausgewählt ist aus 1 und 2, und

* eine Bindungsstelle zu einem benachbarten Atom angibt.


 
5. Organometallische Verbindung nach einem der Ansprüche 1 bis 4, wobei:
A14 bis A16 jeweils unabhängig von einer der Formeln 2-1 bis 2-4 dargestellt werden:

wobei in den Formeln 2-1 bis 2-4

X21 bis X23 jeweils unabhängig ausgewählt sind aus C(R24) und C-*, mit der Maßgabe, dass mindestens zwei von X21 bis X23 jeweils C-* sind,

X24 N-* ist und X25 und X26 jeweils unabhängig ausgewählt sind aus C(R24) und C-*, mit der Maßgabe, dass mindestens eines von X25 und X26 C-* ist,

R21 bis R22 jeweils unabhängig dieselben wie im Zusammenhang mit R11 in Formel 1 beschrieben sind,

b21 ausgewählt ist aus 1, 2 und 3, und

* eine Bindungsstelle zu einem benachbarten Atom angibt.


 
6. Organometallische Verbindung nach einem der Ansprüche 1 bis 5, wobei: in Formel 1
ein von

dargestellter Rest ein Rest ist, der von einer der Formeln 1-1 bis 1-64 dargestellt wird:































wobei in den Formeln 1-1 bis 1-64

Y14 dasselbe wie in Anspruch 1 beschrieben ist, und

*, *'und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben.


 
7. Organometallische Verbindung nach einem der Ansprüche 1 bis 6, wobei:

Y11, Y12 und Y13 jeweils C sind und Y14 N ist;

Y11, Y12 und Y14 jeweils C sind und Y13 N ist;

Y11, Y13 und Y14 jeweils C sind und Y12 N ist;

Y12, Y13 und Y14 jeweils C sind und Y11 N ist;

Y11 und Y14 jeweils C sind und Y12 und Y13 jeweils N sind;

Y11 und Y14 jeweils N sind und Y12 und Y13 jeweils C sind;

Y11 und Y12 jeweils C sind und Y13 und Y14 jeweils N sind;

Y11 und Y12 jeweils N sind und Y13 und Y14 jeweils C sind;

Y11 und Y13 jeweils C sind und Y12 und Y14 jeweils N sind; oder

Y11 und Y13 jeweils N sind und Y12 und Y14 jeweils C sind.


 
8. Organometallische Verbindung nach einem der Ansprüche 1 bis 7, wobei:

T11 bis T14 jeweils eine Einzelbindung sind;

T11 ausgewählt ist aus *-O-*' und *-S-*', und T12 bis T14 jeweils eine Einzelbindung sind;

T12 ausgewählt ist aus *-O-*' und *-S-*', und T11, T13 und T14 jeweils eine Einzelbindung sind;

T13 ausgewählt ist aus *-O-*' und *-S-*', und T11, T12 und T14 jeweils eine Einzelbindung sind; oder

T14 ausgewählt ist aus *-O-*' und *-S-*', und T11, T12 und T13 jeweils eine Einzelbindung sind.


 
9. Organometallische Verbindung nach einem der Ansprüche 1 bis 8, wobei: L11 bis L13 jeweils unabhängig ausgewählt sind aus einer Einzelbindung, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-B(R17)-*', *-N(R17)-*', *-Si(R17)(R18)-*' und *-P(R17)(R18)-*'.
 
10. Organometallische Verbindung nach einem der Ansprüche 1 bis 9, wobei:

L11 *-N(R17)-*', *-C(R17)(R18)-*' oder *-Si(R17)(R18)-*' ist und R17 und R12 verknüpft sind, um eine substituierte oder unsubstituierte heterocyclische C1-C60-Gruppe zu bilden, oder

L12 *-N(R17)-*', *-C(R17)(R18)-*' oder *-Si(R17)(R18)-*' ist und R17 und R13 verknüpft sind, um eine substituierte oder unsubstituierte heterocyclische C1-C60-Gruppe zu bilden.


 
11. Organometallische Verbindung nach einem der Ansprüche 1 bis 10, wobei:

a11 0 ist und a12 und a13 jeweils unabhängig ausgewählt sind aus 1, 2 und 3;

a12 0 ist und a11 und a13 jeweils unabhängig ausgewählt sind aus 1, 2 und 3; oder

a13 0 ist und a11 und a12 jeweils unabhängig ausgewählt sind aus 1, 2 und 3.


 
12. Organometallische Verbindung nach einem der Ansprüche 1 bis 11, wobei a11 0 ist.
 
13. Organometallische Verbindung nach einem der Ansprüche 1 bis 12, wobei:
R11 bis R18 jeweils unabhängig ausgewählt sind aus der Gruppe bestehend aus:

Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Cyanogruppe, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe;

einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, -Br, -I, einer Cyanogruppe, einer Phenylgruppe und einer Biphenylgruppe;

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, einer Pentalenylgruppe, einer Indenylgruppe, einer Naphthylgruppe, einer Azulenylgruppe, einer Indacenylgruppe, einer Acenaphthylgruppe, einer Fluorenylgruppe, einer spiro-Bifluorenylgruppe, einer Benzofluorenylgruppe, einer Dibenzofluorenylgruppe, einer Phenalenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Perylenylgruppe, einer Pentacenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Silolylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Indolylgruppe, einer Isoindolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Isochinolinylgruppe, einer Phthalazinylgruppe, einer Naphthyridinylgruppe, einer Chinoxalinylgruppe, einer Benzochinoxalinylgruppe, einer Chinazolinylgruppe, einer Benzochinazolinylgruppe, einer Cinnolinylgruppe, einer Phenanthridinylgruppe, einer Acridinylgruppe, einer Phenanthrolinylgruppe, einer Phenazinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Benzosilolylgruppe, einer Benzothiazolylgruppe, einer Benzoisothiazolylgruppe, einer Benzoxazolylgruppe, einer Benzoisoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Thiadiazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Dibenzosilolylgruppe, einer Benzocarbazolylgruppe, einer Naphthobenzofuranylgruppe, einer Naphthobenzothiophenylgruppe, einer Naphthobenzosilolylgruppe, einer Dibenzocarbazolylgruppe, einer Dinaphthofuranylgruppe, einer Dinaphthothiophenylgruppe, einer Dinaphthosilolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Oxazolopyridinylgruppe, einer Thiazolopyridinylgruppe, einer Benzonaphthyridinylgruppe, einer Azafluorenylgruppe, einer azaspiro-Bifluorenylgruppe, einer Azacarbazolylgruppe, einer Azadibenzofuranylgruppe, einer Azadibenzothiophenylgruppe, einer Azadibenzosilolylgruppe, einer Indenopyrrolylgruppe, einer Indolopyrrolylgruppe, einer Indenocarbazolylgruppe und einer Indolocarbazolylgruppe;

einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, einer Pentalenylgruppe, einer Indenylgruppe, einer Naphthylgruppe, einer Azulenylgruppe, einer Indacenylgruppe, einer Acenaphthylgruppe, einer Fluorenylgruppe, einer spiro-Bifluorenylgruppe, einer Benzofluorenylgruppe, einer Dibenzofluorenylgruppe, einer Phenalenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Perylenylgruppe, einer Pentacenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Silolylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Indolylgruppe, einer Isoindolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Isochinolinylgruppe, einer Phthalazinylgruppe, einer Naphthyridinylgruppe, einer Chinoxalinylgruppe, einer Benzochinoxalinylgruppe, einer Chinazolinylgruppe, einer Benzochinazolinylgruppe, einer Cinnolinylgruppe, einer Phenanthridinylgruppe, einer Acridinylgruppe, einer Phenanthrolinylgruppe, einer Phenazinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Benzosilolylgruppe, einer Benzothiazolylgruppe, einer Benzoisothiazolylgruppe, einer Benzoxazolylgruppe, einer Benzoisoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Thiadiazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Dibenzosilolylgruppe, einer Benzocarbazolylgruppe, einer Naphthobenzofuranylgruppe, einer Naphthobenzothiophenylgruppe, einer Naphthobenzosilolylgruppe, einer Dibenzocarbazolylgruppe, einer Dinaphthofuranylgruppe, einer Dinaphthothiophenylgruppe, einer Dinaphthosilolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Oxazolopyridinylgruppe, einer Thiazolopyridinylgruppe, einer Benzonaphthyridinylgruppe, einer Azafluorenylgruppe, einer azaspiro-Bifluorenylgruppe, einer Azacarbazolylgruppe, einer Azadibenzofuranylgruppe, einer Azadibenzothiophenylgruppe, einer Azadibenzosilolylgruppe, einer Indenopyrrolylgruppe, einer Indolopyrrolylgruppe, einer Indenocarbazolylgruppe und einer Indolocarbazolylgruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, -Br, -I, einer Cyanogruppe, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Phenylgruppe, einer Biphenylgruppe, einer Terphenylgruppe, einer Pentalenylgruppe, einer Indenylgruppe, einer Naphthylgruppe, einer Azulenylgruppe, einer Indacenylgruppe, einer Acenaphthylgruppe, einer Fluorenylgruppe, einer spiro-Bifluorenylgruppe, einer Benzofluorenylgruppe, einer Dibenzofluorenylgruppe, einer Phenalenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Perylenylgruppe, einer Pentacenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Silolylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Indolylgruppe, einer Isoindolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Isochinolinylgruppe, einer Phthalazinylgruppe, einer Naphthyridinylgruppe, einer Chinoxalinylgruppe, einer Benzochinoxalinylgruppe, einer Chinazolinylgruppe, einer Benzochinazolinylgruppe, einer Cinnolinylgruppe, einer Phenanthridinylgruppe, einer Acridinylgruppe, einer Phenanthrolinylgruppe, einer Phenazinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Benzosilolylgruppe, einer Benzothiazolylgruppe, einer Benzoisothiazolylgruppe, einer Benzoxazolylgruppe, einer Benzoisoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Thiadiazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Carbazolylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Dibenzosilolylgruppe, einer Benzocarbazolylgruppe, einer Naphthobenzofuranylgruppe, einer Naphthobenzothiophenylgruppe, einer Naphthobenzosilolylgruppe, einer Dibenzocarbazolylgruppe, einer Dinaphthofuranylgruppe, einer Dinaphthothiophenylgruppe, einer Dinaphthosilolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Oxazolopyridinylgruppe, einer Thiazolopyridinylgruppe, einer Benzonaphthyridinylgruppe, einer Azafluorenylgruppe, einer azaspiro-Bifluorenylgruppe, einer Azacarbazolylgruppe, einer Azadibenzofuranylgruppe, einer Azadibenzothiophenylgruppe, einer Azadibenzosilolylgruppe, einer Indenopyrrolylgruppe, einer Indolopyrrolylgruppe, einer Indenocarbazolylgruppe, einer Indolocarbazolylgruppe, -Si(Q31)(Q32)(Q33), -N(Q31)(Q32),-B(Q31)(Q32), -C(=O)(Q31), -S(=O)(Q31), -S(=O)2(Q31), -P(=O)(Q31)(Q32) und-P(=S)(Q31)(Q32); und

-Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1),-S(=O)2(Q1), -P(=O)(Q1)(Q2) und -P(=S)(Q1)(Q2), und

Q1 bis Q3 und Q31 bis Q33 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazinogruppe, einer Hydrazonogruppe, 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 C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, einer C1-C60-Alkylgruppe, substituiert durch mindestens eines ausgewählt aus Deuterium, -F, und einer Cyanogruppe, einer C6-C60-Arylgruppe, substituiert durch mindestens eines ausgewählt aus Deuterium, -F und einer Cyanogruppe, einer Biphenylgruppe und einer Terphenylgruppe.


 
14. Organometallische Verbindung nach einem der Ansprüche 1 bis 13, wobei:
die organometallische Verbindung von einer der Formeln 3-1 oder 3-2 dargestellt wird:





wobei in den Formeln 3-1 und 3-2

M11, A11 bis A13, Y11 bis Y14, T11 bis T14, L11 bis L13, a11 bis a13, R11 bis R13 und b11 bis b13 dieselben wie in einem der Ansprüche 1 bis 13 beschrieben sind,

Y31 bis Y37 jeweils unabhängig N oder C sind,

Y41 bis Y47 jeweils unabhängig N oder C sind,

R31 bis R33 jeweils unabhängig dieselben wie im Zusammenhang mit R14 in Anspruch 1 beschrieben sind,

R41 bis R43 jeweils unabhängig dieselben wie im Zusammenhang mit R13 in Anspruch 1 beschrieben sind,

b31, b32, b41 und b42 jeweils unabhängig 1 oder 2 sind, und

b33 und b43 jeweils unabhängig 1, 2 oder 3 sind.


 
15. Organometallische Verbindung nach Anspruch 1, wobei:
die von Formel 1 dargestellte organometallische Verbindung ausgewählt ist aus den Verbindungen 1 bis 45:
























 
16. Organische Leuchtvorrichtung, umfassend:

eine erste Elektrode;

eine zweite Elektrode; und

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

wobei die organische Schicht eine Emissionsschicht und eine organometallische Verbindung nach einem der Ansprüche 1 bis 15 umfasst.


 
17. Organische Leuchtvorrichtung nach Anspruch 16, wobei:

die erste Elektrode eine Anode ist,

die zweite Elektrode eine Kathode ist,

die organische Schicht ferner einen Lochtransportbereich zwischen der ersten Elektrode und der Emissionsschicht und einen Elektronentransportbereich zwischen der Emissionsschicht und der zweiten Elektrode umfasst,

der Lochtransportbereich mindestens eine Schicht umfasst, die ausgewählt ist aus einer Lochinjektionsschicht, einer Lochtransportschicht, einer Pufferschicht, einer Emissionshilfsschicht und einer Elektronensperrschicht, und

der Elektronentransportbereich mindestens eine Schicht umfasst, die ausgewählt ist aus einer Lochsperrschicht, einer Elektronentransportschicht und einer Elektroneninj ektionsschicht.


 
18. Organische Leuchtvorrichtung nach Anspruch 17, wobei: die Emissionsschicht die organometallische Verbindung umfasst.
 
19. Organische Leuchtvorrichtung nach Anspruch 18, wobei:

die Emissionsschicht ferner einen Wirt umfasst, und

der Wirt eine Carbazol enthaltende Verbindung umfasst.


 
20. Organische Leuchtvorrichtung nach einem der Ansprüche 17 bis 19, wobei:

der Elektronentransportbereich die Lochsperrschicht umfasst, und

die Lochsperrschicht eine Phosphinoxid enthaltende Verbindung oder eine Silyl enthaltende Verbindung umfasst.


 


Revendications

1. Composé organométallique représenté par la formule 1 :

où, dans la formule 1

M11 est choisi parmi le platine (Pt), le palladium (Pd), le cuivre (Cu), l'argent (Ag), l'or (Au), le rhodium (Rh), l'iridium (Ir), le ruthénium (Ru), l'osmium (Os), le titane (Ti), le zirconium (Zr), le hafnium (Hf), l'europium (Eu), le terbium (Tb) et le thulium (Tm),

chacun de A11 à A16 est indépendamment choisi parmi un groupe carbocyclique en C5 à C60 et un groupe hétérocyclique en C1 à C60,

chacun de Y11 à Y14 est indépendamment N ou C,

chacun de T11 à T14 est indépendamment choisi parmi une liaison simple, *-O-*', et *-S-*',

chacun de L11 à L13 est indépendamment choisi parmi une liaison simple, *-O-*', *-S-*', *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-C(R17)=C(R18)-*', *-C(=O)-*', *-C(=S)-*', *-C=C-*', *-B(R17)-*', *-N(R17)-*', *-P(R17)-*', *-Si(R17)(R18)-*', *-P(R17)(R18)-*', et *-Ge(R17)(R18)-*',

chacun de a11 à a13 est indépendamment choisi parmi 0, 1, 2 et 3,

quand a11 vaut zéro, A11 et A12 ne sont pas liés l'un à l'autre,

quand a12 vaut zéro, A12 et A13 ne sont pas liés l'un à l'autre,

quand a13 vaut zéro, A13 et A14 ne sont pas liés l'un à l'autre,

chacun de R11 à R18 est indépendamment choisi parmi l'hydrogène, le deutérium, - F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60 substitué ou non substitué, un groupe alcényle en C2 à C60 substitué ou non substitué, un groupe alcynyle en C2 à C60 substitué ou non substitué, un groupe alcoxy en C1 à C60 substitué ou non substitué, un groupe cycloalkyle en C3 à C10 substitué ou non substitué, un groupe hétérocycloalkyle en C1 à C10 substitué ou non substitué, un groupe cycloalcényle en C3 à C10 substitué ou non substitué, un groupe hétérocycloalcényle en C1 à C10 substitué ou non substitué, un groupe aryle en C6 à C60 substitué ou non substitué, un groupe aryloxy en C6 à C60 substitué ou non substitué, un groupe arylthio en C6 à C60 substitué ou non substitué, un groupe hétéroaryle en C1 à C60 substitué ou non substitué, un groupe hétéroaryloxy en C1 à C60 substitué ou non substitué, un groupe hétéroarylthio en C1 à C60 substitué ou non substitué, un groupe polycyclique condensé non aromatique monovalent substitué ou non substitué, un groupe hétéropolycyclique condensé non aromatique monovalent substitué ou non substitué, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1),-S(=O)2(Q1), -P(=O)(Q1)(Q2), et -P(=S)(Q1)(Q2),

R16 et R11, ou R17 et R14, sont éventuellement liés pour former un groupe carbocyclique en C5 à C60 substitué ou non substitué ou un groupe hétérocyclique en C1 à C60 substitué ou non substitué,

R14 et R15, ou R15 et R16, sont éventuellement liés pour former un groupe carbocyclique en C5 à C60 substitué ou non substitué ou un groupe hétérocyclique en C1 à C60 substitué ou non substitué,

R17 et R11, R17 et R12, ou R17 et R13 sont éventuellement liés pour former un groupe carbocyclique en C5 à C60 substitué ou non substitué ou un groupe hétérocyclique en C1 à C60 substitué ou non substitué,

chacun de b11 à b16 est indépendamment choisi parmi 1, 2, 3, 4, 5, 6, 7 et 8,

chacun de Q1 à Q3 est indépendamment choisi parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, un groupe alcoxy en C1 à C60, un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe aryloxy en C6 à C60, un groupe arylthio en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe hétéroaryloxy en C1 à C60, un groupe hétéroarylthio en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, un groupe biphényle, et un groupe terphényle,

chacun de * et *' indique un site de liaison à un atome voisin,

au moins un substituant du groupe carbocyclique en C4 à C60 substitué, du groupe carbocyclique en C5 à C60 substitué, du groupe hétérocyclique en C1 à C60 substitué, du groupe hétérocyclique en C2 à C60 substitué, du groupe alkyle en C1 à C60 substitué, du groupe alcényle en C2 à C60 substitué, du groupe alcynyle en C2 à C60 substitué, du groupe alcoxy en C1 à C60 substitué, du groupe cycloalkyle en C3 à C10 substitué, du groupe hétérocycloalkyle en C1 à C10 substitué, du groupe cycloalcényle en C3 à C10 substitué, du groupe hétérocycloalcényle en C1 à C10 substitué, du groupe aryle en C6 à C60 substitué, du groupe aryloxy en C6 à C60 substitué, du groupe arylthio en C6 à C60 substitué, du groupe hétéroaryle en C1 à C60 substitué, du groupe hétéroaryloxy en C1 à C60 substitué, du groupe hétéroarylthio en C1 à C60 substitué, du groupe polycyclique condensé non aromatique monovalent substitué, et du groupe hétéropolycyclique condensé non aromatique monovalent substitué est choisi dans l'ensemble constitué par :

le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, et un groupe alcoxy en C1 à C60 ;

un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, et un groupe alcoxy en C1 à C60, chacun substitué par au moins l'un choisi parmi le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe aryloxy en C6 à C60, un groupe arylthio en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, -Si(Q11)(Q12)(Q13), -N(Q11)(Q12), -B(Q11)(Q12),-C(=O)(Q11), -S(=O)2(Q11) et -P(=O)(Q11)(Q12) ;

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

un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe aryloxy en C6 à C60, un groupe arylthio en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, et un groupe hétéropolycyclique condensé non aromatique monovalent, chacun substitué par au moins l'un choisi parmi le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, un groupe alcoxy en C1 à C60, un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe aryloxy en C6 à C60, un groupe arylthio en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, -Si(Q21)(Q22)(Q23), -N(Q21)(Q22), -B(Q21)(Q22),-C(=O)(Q21), -S(=O)2(Q21), et -P(=O)(Q21)(Q22) ; et
-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31), et-P(=O)(Q31)(Q32), et

chacun de Q1 à Q3, Q11 à Q13, Q21 à Q23, et Q31 à Q33 est indépendamment choisi parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, un groupe alcoxy en C1 à C60, un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, un groupe alkyle en C1 à C60 substitué par au moins l'un choisi parmi le deutérium, -F, et un groupe cyano, un groupe aryle en C6 à C60 substitué par au moins l'un choisi parmi le deutérium, -F, et un groupe cyano ; un groupe biphényle, et un groupe terphényle.


 
2. Composé organométallique selon la revendication 1, dans lequel : M11 est choisi parmi Pt, Pd, Cu, Ag et Au.
 
3. Composé organométallique selon la revendication 1 ou la revendication 2, dans lequel :
chacun de A11 à A16 est indépendamment choisi parmi un groupe benzène, un groupe naphtalène, un groupe anthracène, un groupe phénanthrène, un groupe triphénylène, un groupe pyrène, un groupe chrysène, un groupe cyclopentadiène, un groupe 1,2,3,4-tétrahydronaphtalène, un groupe furane, un groupe thiophène, un groupe silole, un groupe indène, un groupe fluorène, un groupe indole, un groupe carbazole, un groupe benzofurane, un groupe dibenzofurane, un groupe benzothiophène, un groupe dibenzothiophène, un groupe benzosilole, un groupe dibenzosilole, un groupe indénopyridine, un groupe indolopyridine, un groupe benzofuropyridine, un groupe benzothiénopyridine, un groupe benzosilolopyridine, un groupe indénopyrimidine, un groupe indolopyrimidine, un groupe benzofuropyrimidine, un groupe benzothiénopyrimidine, un groupe benzosilolopyrimidine, un groupe dihydropyridine, un groupe pyridine, un groupe pyrimidine, un groupe pyrazine, un groupe pyridazine, un groupe triazine, un groupe quinoline, un groupe isoquinoline, un groupe quinoxaline, un groupe quinazoline, un groupe phénanthroline, un groupe pyrrole, un groupe pyrazole, un groupe imidazole, un groupe 2,3-dihydroimidazole, un groupe triazole, un groupe 2,3-dihydrotriazole, un groupe oxazole, un groupe isoxazole, un groupe thiazole, un groupe isothiazole, un groupe oxadiazole, un groupe thiadiazole, un groupe benzopyrazole, un groupe benzimidazole, un groupe 2,3-dihydrobenzimidazole, un groupe imidazopyridine, un groupe 2,3-dihydroimidazopyridine, un groupe imidazopyrimidine, un groupe 2,3-dihydroimidazopyrimidine, un groupe imidazopyrazine, un groupe 2,3-dihydroimidazopyrazine, un groupe benzoxazole, un groupe benzothiazole, un groupe benzoxadiazole, un groupe benzothiadiazole, un groupe 5,6,7,8-tétrahydroisoquinoline, et un groupe 5,6,7,8-tétrahydroquinoline.
 
4. Composé organométallique selon l'une quelconque des revendications 1 à 3, dans lequel :
chacun de A11 à A13 est indépendamment représenté par l'une des formules 2-1 à 2-43 :













où, dans les formules 2-1 à 2-43,

chacun de X21 à X23 est indépendamment choisi parmi C(R24) et C-*, sous réserve qu'au moins deux parmi X21 à X23 soient chacun C-*,

X24 est N-*, et chacun de X25 et X26 est indépendamment choisis parmi C(R24) et C-*, sous réserve qu'au moins l'un parmi X25 et X26 soit C-*,

chacun de X27 et X28 est indépendamment choisi parmi N, N(R25) et N-*, et X29 est choisi parmi C(R24) et C-*, où i) au moins l'un parmi X27 et X28 est N-* et X29 est C-* ; ou ii) chacun de X27 et X28 est N-* et X29 est C(R24),

chacun de R21 à R24 est indépendamment tel que décrit en relation avec R11 dans la formule 1,

b21 est choisi parmi 1, 2 et 3,

b22 est choisi parmi 1, 2, 3, 4 et 5,

b23 est choisi parmi 1, 2, 3 et 4,

b24 est choisi parmi 1 et 2, et

* indique un site de liaison à un atome voisin.


 
5. Composé organométallique selon l'une quelconque des revendications 1 à 4, dans lequel :
chacun de A14 à A16 est indépendamment représenté par l'une des formules 2-1 à 2-4 :

où, dans les formules 2-1 à 2-4,

chacun de X21 à X23 est indépendamment choisi parmi C(R24) et C-*, sous réserve qu'au moins deux parmi X21 à X23 soient chacun C-*,

X24 est N-*, et chacun de X25 et X26 est indépendamment choisi parmi C(R24) et C-*, sous réserve qu'au moins l'un parmi X25 et X26 soit C-*,

chacun de R21 et R22 est indépendamment tel que décrit en relation avec R11 dans la formule 1,

b21 est choisi parmi 1, 2 et 3, et

* indique un site de liaison à un atome voisin.


 
6. Composé organométallique selon l'une quelconque des revendications 1 à 5, dans lequel : dans la formule 1,
un fragment représenté par

est un fragment représenté par l'une des formules 1-1 à 1-64 :































où, dans les formules 1-1 à 1-64,

Y14 est tel que décrit dans la revendication 1, et

chacun de *, *' et *" indique un site de liaison à un atome voisin.


 
7. Composé organométallique selon l'une quelconque des revendications 1 à 6, dans lequel :

chacun de Y11, Y12 et Y13 est C, et Y14 est N ;

chacun de Y11, Y12 et Y14 est C, et Y13 est N ;

chacun de Y11, Y13 et Y14 est C, et Y12 est N ;

chacun de Y12, Y13 et Y14 est C, et Y11 est N ;

chacun de Y11 et Y14 est C, et chacun de Y12 et Y13 est N ;

chacun de Y11 et Y14 est N, et chacun de Y12 et Y13 est C ;

chacun de Y11 et Y12 est C, et chacun de Y13 et Y14 est N ;

chacun de Y11 et Y12 est N, et chacun de Y13 et Y14 est C ;

chacun de Y11 et Y13 est C, et chacun de Y12 et Y14 est N ; ou

chacun de Y11 et Y13 est N, et chacun de Y12 et Y14 est C.


 
8. Composé organométallique selon l'une quelconque des revendications 1 à 7, dans lequel :

chacun de T11 à T14 est une liaison simple ;

T11 est choisi parmi *-O-*' et *-S-*', et chacun de T12 à T14 est une liaison simple ;

T12 est choisi parmi *-O-*' et *-S-*', et chacun de T11, T13 et T14 est une liaison simple ;

T13 est choisi parmi *-O-*' et *-S-*', et chacun de T11, T12 et T14 est une liaison simple ; ou

T14 est choisi parmi *-O-*' et *-S-*', et chacun de T11, T12 et T13 est une liaison simple.


 
9. Composé organométallique selon l'une quelconque des revendications 1 à 8, dans lequel :
chacun de L11 à L13 est indépendamment choisi parmi une liaison simple, *-O-*', *-S-*' *-C(R17)(R18)-*', *-C(R17)=*', *=C(R17)-*', *-B(R17)-*', *-N(R17)-*', *-Si(R17)(R18)-*', et *-P(R17)(R18)-*'.
 
10. Composé organométallique selon l'une quelconque des revendications 1 à 9, dans lequel :

L11 est *-N(R17)-*', *-C(R17)(R18)-*', ou *-Si(R17)(R18)-*', et R17 et R12 sont liés pour former un groupe hétérocyclique en C1 à C60 substitué ou non substitué, ou

L12 est *-N(R17)-*', *-C(R17)(R18)-*', ou *-Si(R17)(R18)-*', et R17 et R13 sont liés pour former un groupe hétérocyclique en C1 à C60 substitué ou non substitué.


 
11. Composé organométallique selon l'une quelconque des revendications 1 à 10, dans lequel :

a11 vaut 0, et chacun de a12 et a13 est indépendamment choisi parmi 1, 2 et 3 ;

a12 vaut 0, et chacun de a11 et a13 est indépendamment choisi parmi 1, 2 et 3 ; ou

a13 vaut 0, et chacun de a11 et a12 est indépendamment choisi parmi 1, 2 et 3.


 
12. Composé organométallique selon l'une quelconque des revendications 1 à 11, dans lequel a11 vaut 0.
 
13. Composé organométallique selon l'une quelconque des revendications 1 à 12, dans lequel :
chacun de R11 à R18 est indépendamment choisi dans l'ensemble constitué par :

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

un groupe alkyle en C1 à C20 et un groupe alcoxy en C1 à C20, chacun substitué par au moins l'un choisi parmi le deutérium, -F, -Cl, -Br, -I, un groupe cyano, un groupe phényle, et un groupe biphényle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe pentalényle, un groupe indényle, un groupe naphtyle, un groupe azulényle, un groupe indacényle, un groupe acénaphtyle, un groupe fluorényle, un groupe spiro-bifluorényle, un groupe benzofluorényle, un groupe dibenzofluorényle, un groupe phénalényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysényle, un groupe pérylényle, un groupe pentacényle, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe silolyle, 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 indolyle, un groupe isoindolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe isoquinolinyle, un groupe phtalazinyle, un groupe naphtyridinyle, un groupe quinoxalinyle, un groupe benzoquinoxalinyle, un groupe quinazolinyle, un groupe benzoquinazolinyle, un groupe cinnolinyle, un groupe phénanthridinyle, un groupe acridinyle, un groupe phénanthrolinyle, un groupe phénazinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe benzosilolyle, un groupe benzothiazolyle, un groupe benzisothiazolyle, un groupe benzoxazolyle, un groupe benzisoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe thiadiazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe dibenzosilolyle, un groupe benzocarbazolyle, un groupe naphtobenzofuranyle, un groupe naphtobenzothiophényle, un groupe naphtobenzosilolyle, un groupe dibenzocarbazolyle, un groupe dinaphtofuranyle, un groupe dinaphtothiophényle, un groupe dinaphtosilolyle, un groupe imidazopyridinyle, un groupe imidazopyrimidinyle, un groupe oxazolopyridinyle, un groupe thiazolopyridinyle, un groupe benzonaphtyridinyle, un groupe azafluorényle, un groupe azaspiro-bifluorényle, un groupe azacarbazolyle, un groupe azadibenzofuranyle, un groupe azadibenzothiophényle, un groupe azadibenzosilolyle, un groupe indénopyrrolyle, un groupe indolopyrrolyle, un groupe indénocarbazolyle, et un groupe indolocarbazolyle ;

un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe pentalényle, un groupe indényle, un groupe naphtyle, un groupe azulényle, un groupe indacényle, un groupe acénaphtyle, un groupe fluorényle, un groupe spiro-bifluorényle, un groupe benzofluorényle, un groupe dibenzofluorényle, un groupe phénalényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysényle, un groupe pérylényle, un groupe pentacényle, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe silolyle, 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 indolyle, un groupe isoindolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe isoquinolinyle, un groupe phtalazinyle, un groupe naphtyridinyle, un groupe quinoxalinyle, un groupe benzoquinoxalinyle, un groupe quinazolinyle, un groupe benzoquinazolinyle, un groupe cinnolinyle, un groupe phénanthridinyle, un groupe acridinyle, un groupe phénanthrolinyle, un groupe phénazinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe benzosilolyle, un groupe benzothiazolyle, un groupe benzisothiazolyle, un groupe benzoxazolyle, un groupe benzisoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe thiadiazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe dibenzosilolyle, un groupe benzocarbazolyle, un groupe naphtobenzofuranyle, un groupe naphtobenzothiophényle, un groupe naphtobenzosilolyle, un groupe dibenzocarbazolyle, un groupe dinaphtofuranyle, un groupe dinaphtothiophényle, un groupe dinaphtosilolyle, un groupe imidazopyridinyle, un groupe imidazopyrimidinyle, un groupe oxazolopyridinyle, un groupe thiazolopyridinyle, un groupe benzonaphtyridinyle, un groupe azafluorényle, un groupe azaspiro-bifluorényle, un groupe azacarbazolyle, un groupe azadibenzofuranyle, un groupe azadibenzothiophényle, un groupe azadibenzosilolyle, un groupe indénopyrrolyle, un groupe indolopyrrolyle, un groupe indénocarbazolyle, et un groupe indolocarbazolyle, chacun substitué par au moins l'un choisi parmi le deutérium, -F, -Cl, -Br, -I, un groupe cyano, un groupe alkyle en C1 à C20, un groupe alcoxy en C1 à C20, un groupe cyclopentyle, un groupe cyclohexyle, un groupe cycloheptyle, un groupe cyclopentényle, un groupe cyclohexényle, un groupe phényle, un groupe biphényle, un groupe terphényle, un groupe pentalényle, un groupe indényle, un groupe naphtyle, un groupe azulényle, un groupe indacényle, un groupe acénaphtyle, un groupe fluorényle, un groupe spiro-bifluorényle, un groupe benzofluorényle, un groupe dibenzofluorényle, un groupe phénalényle, un groupe phénanthrényle, un groupe anthracényle, un groupe fluoranthényle, un groupe triphénylényle, un groupe pyrényle, un groupe chrysényle, un groupe pérylényle, un groupe pentacényle, un groupe pyrrolyle, un groupe thiophényle, un groupe furanyle, un groupe silolyle, 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 indolyle, un groupe isoindolyle, un groupe indazolyle, un groupe purinyle, un groupe quinolinyle, un groupe isoquinolinyle, un groupe benzoquinolinyle, un groupe isoquinolinyle, un groupe phtalazinyle, un groupe naphtyridinyle, un groupe quinoxalinyle, un groupe benzoquinoxalinyle, un groupe quinazolinyle, un groupe benzoquinazolinyle, un groupe cinnolinyle, un groupe phénanthridinyle, un groupe acridinyle, un groupe phénanthrolinyle, un groupe phénazinyle, un groupe benzimidazolyle, un groupe benzofuranyle, un groupe benzothiophényle, un groupe benzosilolyle, un groupe benzothiazolyle, un groupe benzisothiazolyle, un groupe benzoxazolyle, un groupe benzisoxazolyle, un groupe triazolyle, un groupe tétrazolyle, un groupe thiadiazolyle, un groupe oxadiazolyle, un groupe triazinyle, un groupe carbazolyle, un groupe dibenzofuranyle, un groupe dibenzothiophényle, un groupe dibenzosilolyle, un groupe benzocarbazolyle, un groupe naphtobenzofuranyle, un groupe naphtobenzothiophényle, un groupe naphtobenzosilolyle, un groupe dibenzocarbazolyle, un groupe dinaphtofuranyle, un groupe dinaphtothiophényle, un groupe dinaphtosilolyle, un groupe imidazopyridinyle, un groupe imidazopyrimidinyle, un groupe oxazolopyridinyle, un groupe thiazolopyridinyle, un groupe benzonaphtyridinyle, un groupe azafluorényle, un groupe azaspiro-bifluorényle, un groupe azacarbazolyle, un groupe azadibenzofuranyle, un groupe azadibenzothiophényle, un groupe azadibenzosilolyle, un groupe indénopyrrolyle, un groupe indolopyrrolyle, un groupe indénocarbazolyle, un groupe indolocarbazolyle, -Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)(Q31), -S(=O)2(Q31), -P(=O)(Q31)(Q32), et -P(=S)(Q31)(Q32) ; et

-Si(Q1)(Q2)(Q3), -B(Q1))(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1),-S(=O)2(Q1), -P(=O)(Q1)(Q2), et -P(=S)(Q1)(Q2), et

chacun de Q1 à Q3 et de Q31 à Q33 est indépendamment choisi parmi l'hydrogène, le deutérium, -F, -Cl, -Br, -I, un groupe hydroxyle, un groupe cyano, un groupe nitro, un groupe amidino, un groupe hydrazino, un groupe hydrazono, un groupe alkyle en C1 à C60, un groupe alcényle en C2 à C60, un groupe alcynyle en C2 à C60, un groupe alcoxy en C1 à C60, un groupe cycloalkyle en C3 à C10, un groupe hétérocycloalkyle en C1 à C10, un groupe cycloalcényle en C3 à C10, un groupe hétérocycloalcényle en C1 à C10, un groupe aryle en C6 à C60, un groupe aryloxy en C6 à C60, un groupe arylthio en C6 à C60, un groupe hétéroaryle en C1 à C60, un groupe hétéroaryloxy en C1 à C60, un groupe hétéroarylthio en C1 à C60, un groupe polycyclique condensé non aromatique monovalent, un groupe hétéropolycyclique condensé non aromatique monovalent, un groupe alkyle en C1 à C60 substitué par au moins l'un choisi parmi le deutérium, -F, et un groupe cyano, un groupe aryle en C6 à C60 substitué par au moins l'un choisi parmi le deutérium, -F, et un groupe cyano, un groupe biphényle, et un groupe terphényle.


 
14. Composé organométallique selon l'une quelconque des revendications 1 à 13, lequel composé organométallique est représenté par la formule 3-1 ou 3-2 :





où, dans les formules 3-1 et 3-2,

M11, A11 à A13, Y11 à Y14, T11 à T14, L11 à L13, a11 à a13, R11 à R13, et b11 à b13 sont tels que décrits dans l'une quelconque des revendications 1 à 13,

chacun de Y31 à Y37 est indépendamment N ou C,

chacun de Y41 à Y47 est indépendamment N ou C,

chacun de R31 à R33 est indépendamment tel que décrit en relation avec R14 dans la revendication 1,

chacun de R41 à R43 est indépendamment tel que décrit en relation avec R13 dans la revendication 1,

chacun de b31, b32, b41 et b42 vaut indépendamment 1 ou 2, et

chacun de b33 et b43 vaut indépendamment 1, 2 ou 3.


 
15. Composé organométallique selon la revendication 1, lequel composé organométallique représenté par la formule 1 est choisi parmi les composés 1 à 45 :
























 
16. Dispositif luminescent organique comprenant :

une première électrode ;

une deuxième électrode ; et

une couche organique entre la première électrode et la deuxième électrode,

dans lequel la couche organique comprend une couche d'émission et un composé organométallique selon l'une quelconque des revendications 1 à 15.


 
17. Dispositif luminescent organique selon la revendication 16, dans lequel :

la première électrode est une anode,

la deuxième électrode est une cathode,

la couche organique comprend en outre une région de transport de trous entre la première électrode et la couche d'émission et une région de transport d'électrons entre la couche d'émission et la deuxième électrode,

la région de transport de trous comprend au moins une couche choisie parmi une couche d'injection de trous, une couche de transport de trous, une couche tampon, une couche auxiliaire d'émission, et une couche de blocage d'électrons, et

la région de transport d'électrons comprend au moins une couche choisie parmi une couche de blocage de trous, une couche de transport d'électrons, et une couche d'injection d'électrons.


 
18. Dispositif luminescent organique selon la revendication 17, dans lequel : la couche d'émission comprend le composé organométallique.
 
19. Dispositif luminescent organique selon la revendication 18, dans lequel :

la couche d'émission comprend en outre un hôte, et

l'hôte comprend un composé contenant un carbazole.


 
20. Dispositif luminescent organique selon l'une quelconque des revendications 17 à 19, dans lequel :

la région de transport d'électrons comprend la couche de blocage de trous, et

la couche de blocage de trous comprend un composé contenant un oxyde de phosphine ou un composé contenant un silyle.


 




Drawing






REFERENCES CITED IN THE DESCRIPTION



This list of references cited by the applicant is for the reader's convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description