| (11) | EP 3 392 257 B1 |
| (12) | EUROPEAN PATENT SPECIFICATION |
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| (54) | ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE ORGANOMETALLIC COMPOUND, AND DIAGNOSTIC COMPOSITION INCLUDING THE ORGANOMETALLIC COMPOUND ORGANOMETALLISCHE VERBINDUNG, ORGANISCHE LICHTEMITTIERENDE VORRICHTUNG MIT DER ORGANOMETALLISCHEN VERBINDUNG UND DIAGNOSTISCHE ZUSAMMENSETZUNG MIT DER ORGANOMETALLISCHEN VERBINDUNG COMPOSÉ ORGANOMÉTALLIQUE, DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE LE COMPRENANT ET COMPOSITION DE DIAGNOSTIC COMPRENANT LE COMPOSÉ ORGANOMÉTALLIQUE |
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| 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). |
FIELD OF THE INVENTION
[0001] One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
BACKGROUND OF THE INVENTION
[0002] Organic light-emitting devices (OLEDs) are self-emission devices, which have superior characteristics in terms of a viewing angle, a response time, brightness, a driving voltage, and a response speed, and which produce full-color images.
[0003] A typical organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
[0004] Meanwhile, luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins. An example of the luminescent compounds includes a phosphorescent luminescent compound.
[0005] Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.
[0006] US 2017/040555 discloses tetradentate platinum (II) and palladium (II) complexes as emitters for organic light emitting diodes.
SUMMARY OF THE INVENTION
[0007] Aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.
[0009] An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
In Formula 1,
M may be Pt or Pd,
X1 to X3 may each independently be C or N,
two bonds selected from a bond between X1 and M, a bond between
X2 and M, and a bond between X3 and M may each be a coordinate bond, and the other thereof may be a covalent bond,
Cy1 to Cy5 may each independently be selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
T1 and T2 may each independently be selected from a single bond, *-N[(L6)b6-(R6)]-*', *-B(R6)-*', *-P(R6)-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-Ge(R6)(R7)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R6)=C(R7)-*', *-C(=S)-*', and *-C≡C-*',
L6 may be selected from a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, and a substituted or unsubstituted C1-C30 heterocyclic group,
b6 may be selected from 1 to 3, wherein, when b6 is two or more, two or more groups L6 may be identical to or different from each other,
R6 and R7 may optionally be linked via a first linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
R1 to R7 may each independently be selected from hydrogen, deuterium, -F, -CI, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl 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 C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), - Si(Q3)(Q4)(Q5), and -B(Q6)(Q7CO)(Q8)(Q9),
a1 to a5 may each independently be 0, 1, 2, 3, 4, or 5,
two of groups R1 in the number of a1, groups R2 in the number of a2, groups R3 in the number of a3, groups R4 in the number of a4, and groups R5 in the number of a5 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 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-C1O heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
deuterium, -F, CI, -Br, -I, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, - N(Q11)(Q12), -Si(Q13)(Q14)(Q15), -B(Q16)(Q17), and -P(=O)(Q18)(Q19);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C1O heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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-C1O heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25), -B(Q26)(Q27), and -P(=O)(Q28)(Q29); and
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35), -B(Q36)(Q37), and -P(=O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
[0010] Another aspect of the present disclosure provides an organic light-emitting device including:
a first electrode,
a second electrode, and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer includes an emission layer, and
wherein the organic layer includes at least one organometallic compound described above.
[0012] Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound described above.
BRIEF DESCRIPTION OF THE DRAWING
[0013] These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.
DETAILED DESCRIPTION OF THE EMBODIMENTS
[0014] Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of," when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
[0015] It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
[0016] It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
[0017] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0018] The term "or" means "and/or." It will be further understood that the terms "comprises" and/or "comprising," or "includes" and/or "including" when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
[0019] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
[0020] Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
[0021] "About" or "approximately" as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ± 30%, 20%, 10%, 5% of the stated value.
[0022] In an embodiment, an organometallic compound is provided. The organometallic compound according to an embodiment may be represented by Formula 1 below:
[0023] M in Formula 1 may be selected from a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, and a third-row transition metal of the Periodic Table of Elements.
[0025] In an embodiment, M in Formula 1 may be Pt, but embodiments of the present disclosure are not limited thereto.
[0026] The organometallic compound represented by Formula 1 may be a compound that does not consist of an ion pair of a cation and an anion.
[0028] For example, X1 to X3 in Formula 1 may each be N. In an embodiment, X1 and X2 may each be N, and X3 may be C. In one or more embodiments, X1 and X3 may each be N, and X2 may be C. In one or more embodiments, X2 and X3 may each be N, and X1 may be C, but embodiments of the present disclosure are not limited thereto.
[0029] In Formula 1, two bonds selected from a bond between X1 and M, a bond between X2 and M, and a bond between X3 and M may each be a coordinate bond, and the other thereof may be a covalent bond.
[0030] In an embodiment, in Formula 1,
X1 to X3 may each be N, a bond between X1 and M and a bond between X3 and M may each be a coordinate bond, and a bond between X2 and M may be a covalent bond;
X1 and X2 may each be N, X3 may be C, a bond between X1 and M and a bond between X2 and M may each be a coordinate bond, and a bond between X3 and M may be a covalent bond;
X1 and X3 may each be N, X2 may be C, a bond between X1 and M and a bond between X3 and M may each be a coordinate bond, and a bond between X2 and M may be a covalent bond; or
X2 and X3 may each be N, X1 may be C, a bond between X2 and M and a bond between X3 and M may each be a coordinate bond, and a bond between X1 and M may be a covalent bond.
[0031] Cy1 to Cy5 in Formula 1 may each independently be selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group.
[0032] For example, Cy1 to Cy5 in Formula 1 may each independently be selected from a 5-membered ring, a 6-membered ring, a condensed ring with a 5-membered ring and a 6-membered ring, a condensed ring with two 6-membered rings, and a condensed ring with one 5-membered ring and two 6-membered rings.
[0033] In an embodiment, Cy1 to Cy5 in Formula 1 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 pyrrole group, a thiophene group, a furan group, an indole group, an iso-indole group, a benzoborol group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 pyrazole group, an imidazole group, a triazole group, a tetrazole 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 benzoxazole group, a benzothiazole group, a benzooxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.
[0034] In one or more embodiments, Cy1 to Cy5 in Formula 1 may each independently be a benzene group, a naphthalene group, an indole group, an iso-indole group, a dibenzothiophene group, a dibenzofuran group, an azadibenzothiophene group, an azadibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a pyrazole group, an imidazole group, or a benzimidazole group, but embodiments of the present disclosure are not limited thereto.
[0035] "An azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxide group" as used herein mean hetero-rings that respectively have the same backbones as "a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group", provided that at least one of carbons forming rings thereof is substituted with nitrogen.
[0036] In Formula 1, T1 and T2 may each independently be selected from a single bond, *-N[(L6)b6-(R6)]-*', *-B(R6)-*', *-P(R6)-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-Ge(R6)(R7)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R6)=C(R7)-*', *-C(=S)-*', and *-C=C-*', and * and *' each indicate a binding site to a neighboring atom. R6 and R7 are the same as described below.
[0037] L6 may be selected from a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, and a substituted or unsubstituted C1-C30 heterocyclic group, and b6 may be selected from 1 to 3 (for example, b6 may be 1), wherein, when b6 is two or more, two or more groups L6 may be identical to or different from each other.
[0038] In an embodiment, L6 may be selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group, and a carbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group, and a carbazolylene group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, - CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group,
but embodiments of the present disclosure are not limited thereto.
[0039] R6 and R7 may optionally be linked via a first linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group (for example, a C5-C6 5-membered to 7-membered cyclic group; or a C5-C6 5-membered to 7-membered cyclic group substituted with at least one selected from deuterium, a cyano group, -F, a C1-C10 alkyl group, and a C6-C14 aryl group).
[0040] In an embodiment, T1 and T2 in Formula 1 may each independently be a single bond, *-N[(L6)b6-(R6)]-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-S-*', or *-O-*', but embodiments of the present disclosure are not limited thereto.
[0041] In one or more embodiments, T1 and T2 may each independently be selected from a single bond, *-C(R6)(R7)-*', *-Si(R6)(R7)-*', and *-Ge(R6)(R7)-*',
R6 and R7 may be linked via a single bond or a first linking group,
the first linking group may be selected from *-N[(L8)b8-(R8)]-*', *-B(R8)-*', *-P(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-Ge(R8)(P9)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R8)=*', *=C(R9)-*', *-C(R8)=C(R9)-*', *-C(=S)-*', and *-C=C-*'. L8, b8, R8, and R9 are the same as described in connection with L6, b6, R6, and R7, and * and *' each indicate a binding site to a neighboring atom, but embodiments of the present disclosure are not limited thereto.
[0042] In one or more embodiments, T1 and T2 may each be a single bond, but embodiments of the present disclosure are not limited thereto.
[0043] R1 to R7 may each independently be selected from hydrogen, deuterium, -F, - Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl 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 C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, - N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9). Q1 to Q9 are the same as described herein.
[0044] For example, R1 to R7 may each independently be selected from:
hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, a 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, -CD3, -CD2H, -CDH2, - CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group; and
-N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), and
Q1 to Q9 may each independently be selected from:-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, - CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, - CD2CH3, -CD2CD2H, and -CD2CDH2;
an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group.
[0045] In an embodiment, R1 to R7 may each independently be selected from:
hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group;
a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group, each substituted with at least one selected from deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a cyano group, a nitro group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group; and
-N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), and
Q1 to Q9 are the same as described herein.
[0046] In one or more embodiments, R1 to R7 may each independently be selected from hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, - CD2H, -CDH2, -CF3, -CF2H, -CFH2, groups represented by Formulae 9-1 to 9-22, groups represented by Formulae 10-1 to 10-144, and -Si(Q3)(Q4)(Q5) (wherein Q3 to Q5 are the same as described herein), but embodiments of the present disclosure are not limited thereto:
[0047] In Formulae 9-1 to 9-22 and 10-1 to 10-144, "i-Pr" indicates an iso-propyl group, "i-Bu" indicates an isobutyl group, "t-Bu" indicates a tert-butyl group, "TMS" indicates a trimethylsilyl group, "Ph" indicates a phenyl group, and "*" indicates a binding site to a neighboring atom.
[0049] a1, a2, a3, a4, and a5 in Formula 1 respectively indicate the number of groups R1, the number of groups R2, the number of groups R3, the number of groups R4, and the number of groups R5 and may each independently be 0, 1, 2, 3, 4, or 5. When a1 is two or more, two or more groups R1 may be identical to or different from each other, when a2 is two or more, two or more groups R2 may be identical to or different from each other, when a3 is two or more, two or more groups R3 may be identical to or different from each other, when a4 is two or more, two or more groups R4 may be identical to or different from each other, and when a5 is two or more, two or more groups R5 may be identical to or different from each other, but embodiments of the present disclosure are not limited thereto.
[0050] In an embodiment, in Formula 1, a1, a2, a3, a4, and a5 may each independently be 0, 1, or 2, but embodiments of the present disclosure are not limited thereto.
[0051] In Formula 1, two of groups R1 in the number of a1, groups R2 in the number of a2, groups R3 in the number of a3, groups R4 in the number of a4, and groups R5 in the number of a5 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
[0052] For example, two of groups R1 in the number of a1 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of groups R2 in the number of a2 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of groups R3 in the number of a3 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of groups R4 in the number of a4 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of groups R5 in the number of a5 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, R1 and R2 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, R2 and R3 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, R3 and R4 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, and R1 and R5 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
[0053] For example, i) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking two of groups R1 in the number of a1, ii) a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking two of groups R2 in the number of a2, iii) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, by linking two of groups R3 in the number of a3, iv) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking two of groups R4 in the number of a4, v) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking two of groups R5 in the number of a5, vi) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking R1 and R2, vii) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking R2 and R3, viii) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, by linking R3 and R4, and ix) a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, formed by linking R1 and R5 in Formula 1 may each independently be selected from:
a pentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a bicycloheptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, a phenalene group, a benzothiophene group, a benzofuran group, an indene group, an indole group, a benzosilole group, an azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, and an azabenzosilole group;
a pentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a bicycloheptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, a phenalene group, a benzothiophene group, a benzofuran group, an indene group, an indole group, a benzosilole group, an azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, and an azabenzosilole group, each substituted with at least one R10,
but embodiments of the present disclosure are not limited thereto.
[0055] In an embodiment, a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cy1-1 to Cy1-39 (for example, groups represented by Formulae Cy1-1 to Cy1-4 and Cy1-12 to Cy1-15):
[0056] In Formulae Cy1-1 to Cy1-39,
X1 and R1 are the same as described herein,
X11 may be O, S, N(R11), or C(R11)(R12),
X19 may be C(R19) or N,
R11 to R19 are the same as described in connection with R1,
a13 may be an integer from 0 to 3,
a14 may be an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom.
[0057] In one or more embodiments, a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cy2-1 to Cy2-39 (for example, groups represented by Formulae Cy2-1, Cy2-12 to Cy2-15, Cy2-37, and Cy2-39):
[0058] In Formulae Cy2-1 to Cy2-39,
X2 and R2 are the same as described herein,
X21 may be O, S, N(R21), or C(R21)(R22),
X29 may be C(R29) or N,
R21 to R29 are the same as described in connection with R2,
a23 may be an integer from 0 to 3,
a24 may be an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom.
[0059] In one or more embodiments, a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cy3-1 to Cy3-39 (for example, groups represented by Formulae Cy3-1 to Cy3-4 and Cy3-12 to Cy3-15):
[0060] In Formulae Cy3-1 to Cy3-39,
X3 and R3 are the same as described herein,
X31 may be O, S, N(R31), or C(R31)(R32),
X39 may be C(R39) or N,
R31 to R39 are the same as described in connection with R3,
a33 may be an integer from 0 to 3,
a34 may be an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom.
[0061] In one or more embodiments, a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cz-1 to Cz-27 (for example, groups represented by Formulae Cz-1, Cz-11, and Cz-25):
[0062] In Formulae Cz-1 to Cz-27,
R4 and R5 are the same as described herein,
a42 and a52 may each independently be an integer from 0 to 2,
a43 and a53 may each independently be an integer from 0 to 3,
a45 and a55 may each independently be an integer from 0 to 5, and
*, *', and *" each indicate a binding site to a neighboring atom.
[0063] In one or more embodiments, a moiety represented by
Formula 1 may be selected from groups represented by Formulae Cy1(1) to Cy1 (26), a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cy2(1) to Cy2(15), a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cy3(1) to Cy3(26), and/or a moiety represented by
in Formula 1 may be selected from groups represented by Formulae Cz(1) to Cz(21), but embodiments of the present disclosure are not limited thereto:
[0064] In Formulae Cy1(1) to Cy1(26), Cy2(1) to Cy2(15), Cy3(1) to Cy3(26), and Cz(1) to Cz(21),
X1 to X3 and R1 to R5 are the same as described herein,
X11 may be O, S, N(R11), or C(R11)(R12),
X21 may be O, S, N(R21), or C(R21)(R22),
X31 may be O, S, N(R31), or C(R31)(R32),
R1a to R1c, R11, and R12 are the same as described in connection with R1,
R2a to R2c, R21, and R22 are the same as described in connection with R2,
R3a to R3c, R31, and R32 are the same as described in connection with R3,
R1, R1a to R1c, R2, R2a to R2c, R3, R3a to R3c, R4, and R5 may not be hydrogen, and
*, *', and *" each indicate a binding site to a neighboring atom.
[0066] In Formulae 1-1 to 1-32,
M, X1 to X3, and R1 to R5 are the same as described herein,
X11 may be O, S, N(R11), or C(R11)(R12),
X21 may be O, S, N(R21), or C(R21)(R22),
X31 may be O, S, N(R31), or C(R31)(R32),
R1a, R1b, R11, and R12 are the same as described in connection with R1,
R2a, R2b, R21, and R22 are the same as described in connection with R2, and
R3a, R3b, R31, and R32 are the same as described in connection with R3.
[0067] The organometallic compound represented by Formula 1 may be selected from Compounds 1 to 120, but embodiments of the present disclosure are not limited thereto:
[0068] The organometallic compound represented by Formula 1 has an emission wavelength that is easily adjustable according to a type of a substituent, and has electrical characteristics (for example, a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a triplet (T1) energy level, or the like) suitable for use in an electronic device, for example, an organic light-emitting device. Thus, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound, may have excellent emission efficiency, lifespan, and/or roll-off ratio characteristics.
[0069] For example, a HOMO energy level, a LUMO energy level, and a triplet (T1) energy level of some Compounds and Compound A were evaluated by a density functional theory (DFT) of a Gaussian program (B3LYP, structurally optimized at a level of 6-31G(d,p)). Evaluation results thereof are shown in Table 1.
| Compound No. | HOMO (eV) | LUMO (eV) | T1 energy level (eV) |
| 1 | -4.888 | -1.925 | 2.122 |
| 3 | -4.755 | -1.867 | 2.046 |
| 48 | -4.646 | -1.776 | 2.067 |
| 55 | -4.755 | -1.857 | 2.046 |
| 61 | -5.082 | -2.275 | 1.997 |
| 66 | -4.567 | -2.137 | 1.633 |
| A | -4.418 | -1.584 | 1.971 |
[0070] Referring to Table 1, it has been confirmed that the organometallic compound represented by Formula 1 has such electrical characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device. For example, it is confirmed that the organometallic compound represented by Formula 1 has a relatively low LUMO energy level (that is, a large absolute value of a LUMO energy level).
[0071] Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by those of ordinary skill in the art by referring to Synthesis Examples provided below.
[0072] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer and at least one organometallic compound represented by Formula 1.
[0073] The organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, low driving voltage, high light emission efficiency, high quantum light emission efficiency, and low roll-off ratios.
[0074] The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
[0075] The expression "(an organic layer) includes at least one organometallic compound" as used herein may include an embodiment in which "(an organic layer) includes identical compounds represented by Formula 1" and an embodiment in which "(an organic layer) includes two or more different organometallic compounds represented by Formula 1."
[0076] For example, the organic layer may include, as the organometallic compound, only Compound 1. In this embodiment, 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 embodiment, Compound 1 and Compound 2 may be included in an identical layer (for example, Compound 1 and Compound 2 all may be included in an emission layer).
[0077] The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
[0078] In an embodiment, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and wherein the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0079] The term "organic layer" as used herein refers 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 "organic layer" may include, in addition to an organic compound, an organometallic complex including metal.
[0080] The FIGURE is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
[0081] A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0082] In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
[0083] The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
[0085] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
[0086] The hole transport region may be disposed between the first electrode 11 and the emission layer.
[0087] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
[0088] The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
[0089] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
[0090] When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is 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, and a deposition rate of about 0.01 AÌŠ/sec to about 100 AÌŠ/sec. However, the deposition conditions are not limited thereto.
[0091] When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80°C to about 200°C. However, the coating conditions are not limited thereto.
[0092] Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
[0093] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:
[0094] Ar101 and Ar102 in Formula 201 may each independently be selected from:
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; and
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one selected from deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C1O heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
[0095] xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but embodiments of the present disclosure are not limited thereto.
[0096] R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be selected from:
hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, and so on), and a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);
a C1-C1O alkyl group and a C1-C10 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, and a C1-C10 alkoxy group,
but embodiments of the present disclosure are not limited thereto. R109 in Formula 201 may be selected from:
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, - F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.
[0097] According to an embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but embodiments of the present disclosure are not limited thereto:
[0098] R101, R111, R112, and R109 in Formula 201A may be understood by referring to the description provided herein.
[0099] For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include compounds HT1 to HT20 illustrated below, but embodiments of the present disclosure are not limited thereto:
[0100] A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
[0101] 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.
[0102] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenium oxide; and a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto:
[0104] Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
[0105] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.
[0106] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.
[0107] The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 or the composition containing the organometallic compound described above.
[0108] The host may include at least one selected from TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, and Compound H52:
[0109] In one or more embodiments, the host may further include a compound represented by Formula 301 below:
[0110] Ar111 and Ar112 in Formula 301 may each independently be selected from:
a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and
a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.
[0111] Ar113 to Ar116 in Formula 301 may each independently be selected from:
a C1-C10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.
[0112] g, h, I, and j in Formula 301 may each independently be an integer from 0 to 4, for example, 0, 1, or 2.
[0113] Ar113 to Ar116 in Formula 301 may each independently be selected from:
a C1-C10 alkyl group substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group; and
but embodiments of the present disclosure are not limited thereto.
[0114] In one or more embodiments, the host may include a compound represented by Formula 302 below:
[0115] Ar122 to Ar125 in Formula 302 are the same as described in detail in connection with Ar113 in Formula 301.
[0116] Ar126 and Ar127 in Formula 302 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
[0117] k and I in Formula 302 may each independently be an integer from 0 to 4. For example, k and I may be 0, 1, or 2.
[0118] The compound represented by Formula 301 and the compound represented by Formula 302 may include Compounds H1 to H42 illustrated below, but are not limited thereto:
[0119] When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
[0120] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of 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.
[0121] A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light emission characteristics may be obtained without a substantial increase in driving voltage.
[0123] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0124] For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
[0125] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
[0126] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq but embodiments of the present disclosure are not limited thereto:
[0127] A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a substantial increase in driving voltage.
[0128] The electron transport layer may include at least one selected from BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ:
[0129] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but are not limited thereto:
[0130] A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
[0131] Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
[0132] The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or ET-D2:
[0133] The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.
[0134] The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li2O, and BaO.
[0135] A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
[0136] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be formed as the material for forming the second electrode 19. To manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
[0137] Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.
[0138] Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.
[0139] The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
[0140] The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
[0141] The term "C1-C60 alkyl group" as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof 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 iso-amyl group, and a hexyl group. The term "C1-C60 alkylene group" as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
[0142] The term "C1-C60 alkoxy group" as used herein refers to a monovalent group represented by -OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
[0143] The term "C2-C60 alkenyl group" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term "C2-C60 alkenylene group" as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
[0144] The term "C2-C60 alkynyl group" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term "C2-C60 alkynylene group" as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
[0145] The term "C3-C10 cycloalkyl group" as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof 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 refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
[0146] The term "C1-C10 heterocycloalkyl group" as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term "C1-C10 heterocycloalkylene group" as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
[0147] The term "C3-C10 cycloalkenyl group" as used herein refers to a monovalent hydrocarbon monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and that has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term "C3-C10 cycloalkenylene group," as used herein, refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
[0148] The term "C1-C10 heterocycloalkenyl group" as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term "C1-C10 heterocycloalkenylene group," as used herein, refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
[0149] The term "C6-C60 aryl group" as used herein refers 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 refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group are 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.
[0150] The term "C1-C60 heteroaryl group," as used herein, refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term "C1-C60 heteroarylene group" as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group are 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 fused to each other.
[0151] A C6-C60 aryloxy group as used herein indicates -OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group indicates -SA103 (wherein A103 is the C6-C60 aryl group).
[0152] The term "monovalent non-aromatic condensed polycyclic group" as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term "divalent non-aromatic condensed polycyclic group," as used herein, refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0153] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and having no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0154] The term "C5-C30 carbocyclic group" as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
[0155] The term "C1-C30 heterocyclic group" as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S other than 1 to 30 carbon atoms. The term C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
[0156] At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 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 C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-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, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q11)(Q12), -Si(Q13)(Q14)(Q15), -B(Q16)(Q17), and - P(=O)(Q18)(Q19);
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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, - N(Q21)(Q22), -Si(Q23)(Q24)(Q25), -B(Q26)(Q27), and -P(=O)(Q28)(Q29); and
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35), -B(Q36)(Q37), and -P(=O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
[0157] Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording " 'B' was used instead of 'A' " used in describing Synthesis Examples means that a molar equivalent of 'A' was identical to a molar equivalent of 'B'.
Examples
Synthesis Example 1: Synthesis of Compound 1
1) Synthesis of Intermediate 1-4
[0159] 11.7 grams (g) (36 millimoles, mmol) of Intermediate 1A and 1.45 g (35 mmol) of 60% sodium hydride were dissolved in 400 milliliters (mL) of tetrahydrofuran (THF), stirred at a temperature of -78°C for about 10 minutes, and then stirred at room temperature for about 2 hours. 20 mL (1.76 mmol) of tetrakis(triphenylphosphine)palladium(0) and 79 mL (39.5 mmol) of 0.5 molar (M) 2-pyridylzinc bromide, which were dissolved in THF, were added thereto. The resultant mixture was heated under reflux at a temperature of 80°C for about 16 hours. After the reaction was complete, the resultant mixture was cooled to room temperature, and a saturated sodium hydrogen carbonate aqueous solution was added thereto. The organic layer extracted with dichloromethane was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The compound obtained therefrom was separated and purified by column chromatography to obtain 8.5 g (73%) of Intermediate 1-4. The obtained compound was identified by LC-MS.
2) Synthesis of Intermediate 1-3
[0161] 3.4 g (10.66 mmol) of Intermediate 1-4, 3.3 g (12.80 mmol) of bis(pinacolato)diboron, 3.1 g (31.98 mmol) of potassium acetate, and 0.78 g (1.07 mmol) of Pd(dppf)2Cl2 were mixed with 150 mL of toluene. The resultant mixture was heated to a temperature of 120°C and stirred under reflux for 8 hours. The reactant obtained therefrom was cooled to room temperature, and the organic layer was extracted by using 300 mL of water and 300 mL of ethyl acetate. The extracted organic layer was dried by using MgSO4, and a solvent was evaporated therefrom. The residue obtained therefrom was separated and purified by silica gel column chromatography to obtain 2.3 g (58%) of Intermediate 1-3. The obtained compound was identified by LC-MS.
3) Synthesis of Intermediate 1-2
[0163] 2.3 g (6.18 mmol) of Intermediate 1-3, 1.2 g (5.144 mmol) of Intermediate 1B, 1.36 g (12.86 mmol) of sodium carbonate, and 0.4 g (0.36 mmol) of Pd(PPh3)4 were mixed with 60 mL of THF, 20 mL of distilled water, 20 mL of ethanol. The resultant mixture was heated to a temperature of 100°C and stirred under reflux for 16 hours. The reactant obtained therefrom was cooled to room temperature, and the organic layer was extracted by using 200 mL of water and 200 mL of ethyl acetate. The extracted organic layer was dried by using MgSO4, and a solvent was evaporated therefrom. The residue obtained therefrom was separated and purified by silica gel column chromatography to obtain 2.0 g (81%) of Intermediate 1-2. The obtained compound was identified by LC-MS.
4) Synthesis of Intermediate 1-1
[0165] 2.0 g (5.01 mmol) of Intermediate 1-2, 2.07 g (5.01 mmol) of potassium tetrachloroplatinate, and 100 mL of acetic acid were mixed, and the resultant mixture was heated to a temperature of 130°C and stirred under reflux for 16 hours. The reactant obtained therefrom was cooled to room temperature, and the organic layer was extracted by using a sodium bicarbonate aqueous solution, water, and 200 mL of ethyl acetate. The extracted organic layer was dried by using MgSO4, and the solvent was evaporated therefrom. A residue obtained therefrom was separated and purified by silica gel column chromatography to obtain 1.33 g (45%) of Intermediate 1-1. The obtained compound was identified by LC-MS.
5) Synthesis of Compound 1
[0167] 1.33 g (2.25 mmol) of Intermediate 1-1 was added to a sealed tube and heated to a temperature of 330°C for 45 hours. The reactant obtained therefrom was cooled to room temperature, added to a sublimation purifier, and then slowly heated to remove a remaining reactant, thereby obtaining 0.25 g (19%) of Compound 1. The obtained compound was identified by LC-MS.
Synthesis Example 2: Synthesis of Compound 3
[0169] Compound 3 was synthesized in the same manner as in Synthesis Example 1, except that, in synthesizing Intermediate 1-4, 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole was used instead of Intermediate 1A. The obtained compound was identified by LC-MS.
Synthesis Example 3: Synthesis of Compound 48
[0171] Compound 48 was synthesized in the same manner as in Synthesis Example 1, except that, in synthesizing Compound 1, 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole was used instead of Intermediate 1A, (4-([1,1'-biphenyl]-4-yl)pyridin-2-yl)zinc bromide was used instead of 2-pyridylzinc bromide, and 4-([1,1'-biphenyl]-4-yl)-2-bromo-6-phenylpyridine was used instead of Intermediate 1B. The obtained compound was identified by LC-MS.
Synthesis Example 4: Synthesis of Compound 55
[0173] Compound 55 was synthesized in the same manner as in Synthesis Example 1, except that, in synthesizing Compound 1, 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole was used instead of Intermediate 1A, (5-fluoro-4-phenylpyridin-2-yl)zinc bromide was used instead of 2-pyridylzinc bromide, and 6-bromo-3-fluoro-2,4-diphenylpyridine was used instead of Intermediate 1B. The obtained compound was identified by LC-MS.
Synthesis Example 5: Synthesis of Compound 61
[0175] Compound 61 was synthesized in the same manner as in Synthesis Example 1, except that, in synthesizing Compound 1, 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole was used instead of Intermediate 1A, (5-cyano-4-phenylpyridin-2-yl)zinc bromide was used instead of 2-pyridylzinc bromide, and 6-bromo-2,4-diphenylnicotinonitrile was used instead of Intermediate 1B. The obtained compound was identified by LC-MS.
Example 1
[0177] An ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.5 mm (mm = millimeter), sonicated with acetone, iso-propyl alcohol, pure water each for 15 minutes, and then cleaned by exposure ultraviolet (UV) rays and ozone for 30 minutes.
[0178] Then, m-MTDATA was deposited on an ITO electrode (anode) of the ITO glass substrate at a deposition rate of 1 Angstroms per second (Å/sec) to form a hole injection layer having a thickness of 600 Angstroms (Å), and then, α-NPD was deposited on the hole injection layer at a deposition rate of 1 Å/sec to form a hole transport layer having a thickness of 250 Å.
[0179] Compound 1 (dopant) and CBP (host) were co-deposited on the hole transport layer at a weight ratio of 2 : 98 to form an emission layer having a thickness of 400 Å.
[0180] BAlq was deposited on the emission layer at a deposition rate of 1 Å/sec to form a hole blocking layer having a thickness of 50 Å, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF 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 second electrode (cathode) having a thickness of 1,200 Å, thereby completing the manufacture of an organic light-emitting device having a structure of ITO / m-MTDATA (600 Å) / α-NPD (250 Å) / CBP + Compound 6 (2%) (400 Å) / BAlq (50 Å) / Alq3 (300 Å) / LiF (10 Å) / Al (1,200 Å).
Examples 2 to 5 and Comparative Example A
[0181] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that in forming an emission layer, for use as a dopant, corresponding compounds shown in Table 2 were used instead of Compound 1.
Evaluation Example 1: Evaluation of characteristics of organic light-emitting devices.
[0182] The driving voltage, light emission efficiency, quantum light emission efficiency, roll-off ratio, maximum emission wavelength, and full width at half maximum (FWHM) of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Example A were evaluated by using a voltage-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A), and results thereof are shown in Table 2. The roll ratio was calculated by using Equation 20.
| Dopant Compound No. | Driving voltage (V) | Emission efficiency (cd/A) | Quantum emission efficiency (%) | Roll-off ratio (%) | Maximum emission wavelength (nm) | FWHM (nm) | |
| Example 1 | 1 | 4.48 | 40.2 | 17.4 | 24 | 575 | 56.1 |
| Example 2 | 3 | 4.28 | 37.5 | 18.2 | 21 | 581 | 52.6 |
| Example 3 | 48 | 4.15 | 32.5 | 20.3 | 20 | 604 | 61.3 |
| Example 4 | 55 | 4.46 | 30.8 | 19.3 | 19 | 609 | 67.8 |
| Example 5 | 61 | 4.85 | 26.7 | 17.8 | 22 | 617 | 72.6 |
| Comparative Example A | A | 5.371 | 16.461 | 13.32 | 25.5 | 615 | 68.1 |
[0183] Referring to Table 2, it has been confirmed that the organic light-emitting devices of Examples 1 to 5 have improved driving voltage, emission efficiency, quantum emission efficiency, and roll-off ratio characteristics, as compared with those of the organic light-emitting device of Comparative Example A.
[0184] Since the organometallic compounds have excellent electrical characteristics and thermal stability, organic light-emitting devices including such organometallic compounds may have excellent driving voltage, emission efficiency, quantum emission efficiency, and roll-off ratio characteristics. Also, due to excellent phosphorescent luminescent characteristics, such organometallic compounds may provide a diagnostic composition having high diagnostic efficiency.
[0185] 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.
wherein, in Formula 1,
M is Pt or Pd,
X1 to X3 are each independently C or N,
two bonds selected from a bond between X1 and M, a bond between X2 and M, and a bond between X3 and M are each a coordinate bond, and the other thereof is a covalent bond,
Cy1 to Cy5 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
T1 and T2 are each independently selected from a single bond, *-N[(L6)b6-(Re)]-*', *-B(R6)-*', *-P(R6)-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-Ge(R6)(R7)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R6)=C(R7)-*', *-C(=S)-*', and *-C≡C-*',
L6 is selected from a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, and a substituted or unsubstituted C1-C30 heterocyclic group,
b6 is selected from 1 to 3, wherein, when b6 is two or more, two or more groups L6 are identical to or different from each other,
R6 and R7 are optionally linked via a first linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
R1 to R7 are each independently selected from hydrogen, deuterium, -F, -Cl, - Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl 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 C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, - N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9),
a1 to a5 are each independently 0, 1, 2, 3, 4, or 5,
two of groups R1 in the number of a1, groups R2 in the number of a2, groups R3 in the number of a3, groups R4 in the number of a4, and groups R5 in the number of a5 are optionally linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 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 C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, -F, Cl, -Br, -I, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, -F, - Cl, -Br, -I, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q11)(Q12), - Si(Q13)(Q14)(Q15), -B(Q16)(Q17), and -P(=O)(Q18)(Q19);
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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl 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, -CD3, -CD2H, -CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25), -B(Q26)(Q27), and -P(=O)(Q28)(Q29); and
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35), -B(Q36)(Q37), and -P(=O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
M is Pt.
X1 to X3 are each N, a bond between X1 and M and a bond between X3 and M are each a coordinate bond, and a bond between X2 and M is a covalent bond;
X1 and X3 are each N, X2 is C, a bond between X1 and M and a bond between X3 and M are each a coordinate bond, and a bond between X2 and M is a covalent bond; or
X2 and X3 are each N, X1 is C, a bond between X2 and M and a bond between X3 and M are each a coordinate bond, and a bond between X1 and M is a covalent bond.
Cy1 to Cy5 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 pyrrole group, a thiophene group, a furan group, an indole group, an iso-indole group, a benzoborol group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 pyrazole group, an imidazole group, a triazole group, a tetrazole 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 benzoxazole group, a benzothiazole group, a benzooxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group;
preferably wherein
Cy1 to Cy5 are each independently selected from a benzene group, a naphthalene group, an indole group, an iso-indole group, a dibenzothiophene group, a dibenzofuran group, an azadibenzothiophene group, an azadibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a pyrazole group, and an imidazole group or a benzimidazole group.
T1 and T2 are each a single bond.
R1 to R7 are each independently selected from:
hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, - CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group; and
-N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), and -P(=O)(Q8)(Q9), and
Q1 to Q9 are each independently selected from:
-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, - CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CH3, -CD2CD2H, and - CD2CDH2;
an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group;
preferably wherein
R1 to R7 are each independently selected from hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groups represented by Formulae 9-1 to 9-22, groups represented by Formulae 10-1 to 10-144, and -Si(Q3)(Q4)(Q5):
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy1-1 to Cy1-39:
wherein, in Formulae Cy1-1 to Cy1-39,
X1 and R1 are the same as described in claim 1,
X11 is O, S, N(R11), or C(R11)(R12),
X19 is C(R19) or N,
R11 to R19 are the same as described in connection with R1 in claim 1,
a13 is an integer from 0 to 3,
a14 is an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom; and/or
wherein
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy2-1 to Cy2-39:
wherein, in Formulae Cy2-1 to Cy2-39,
X2 and R2 are the same as described in claim 1,
X21 is O, S, N(R21), or C(R21)(R22),
X29 is C(R29) or N,
R21 to R29 are the same as described in connection with R2 in claim 1,
a23 is an integer from 0 to 3,
a24 is an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom; and/or wherein
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy3-1 to Cy3-39:
wherein, in Formulae Cy3-1 to Cy3-39,
X3 and R3 are the same as described in claim 1,
X31 is O, S, N(R31), or C(R31)(R32),
X39 is C(R39) or N,
R31 to R39 are the same as described in connection with R3 in claim 1,
a33 is an integer from 0 to 3,
a34 is an integer from 0 to 4, and
*, *', and *" each indicate a binding site to a neighboring atom; and/or
wherein
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cz-1 to Cz-27:
wherein, in Formulae Cz-1 to Cz-27,
R4 and R5 are the same as described in claim 1,
a42 and a52 are each independently an integer from 0 to 2,
a43 and a53 are each independently an integer from 0 to 3,
a45 and a55 are each independently an integer from 0 to 5, and
*, *', and *" each indicate a binding site to a neighboring atom.
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy1(1) to Cy1(26),
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy2(1) to Cy2(15),
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cy3(1) to Cy3(26), and
a moiety represented by
in Formula 1 is selected from groups represented by Formulae Cz(1) to Cz(21):
wherein, in Formulae Cy1(1) to Cy1(26), Cy2(1) to Cy2(15), Cy3(1) to Cy3(26), and Cz(1) to Cz(21),
X1 to X3 and R1 to R5 are the same as described in claim 1,
X11 is O, S, N(R11), or C(R11)(R12),
X21 is O, S, N(R21), or C(R21)(R22),
X31 is O, S, N(R31), or C(R31)(R32),
R1a to R1c, R11, and R12 are the same as described in connection with R1 in claim 1,
R2a to R2c, R21, and R22 are the same as described in connection with R2 in claim 1,
R3a to R3c, R31, and R32 are the same as described in connection with R3 in claim 1,
R1, R1a to R1c, R2, R2a to R2c, R3, R3a to R3c, R4, and R5 are not hydrogen, and *, *', and *" each indicate a binding site to a neighboring atom.
the organometallic compound is represented by one of Formulae 1-1 to 1-32:
wherein, in Formulae 1-1 to 1-32,
M, X1 to X3, and R1 to R5 are the same as described in claim 1,
X11 is O, S, N(R11), or C(R11)(R12),
X21 is O, S, N(R21), or C(R21)(R22),
X31 is O, S, N(R31), or C(R31)(R32),
R1a, R1b, R11, and R12 are the same as described in connection with R1 in claim 1,
R2a, R2b, R21, and R22 are the same as described in connection with R2 in claim 1, and
R3a, R3b, R31, and R32 are the same as described in connection with R3 in claim 1.
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, and
wherein the organic layer comprises at least one organometallic compound of any of claims 1-10.
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
the emission layer further comprises a host, and
an amount of the host is larger than an amount of the organometallic compound.
wobei in Formel 1
M für Pt oder Pd steht,
X1 bis X3 jeweils unabhängig für C oder N stehen,
zwei Bindungen, ausgewählt aus einer Bindung zwischen X1 und M, einer Bindung zwischen X2 und M und einer Bindung zwischen X3 und M, jeweils eine koordinative Bindung sind und die andere davon eine kovalente Bindung ist,
Cy1 bis Cy5 jeweils unabhängig ausgewählt sind aus einer carbocyclischen C5-C30-Gruppe und einer heterocyclischen C1-C30-Gruppe,
T1 und T2 jeweils unabhängig ausgewählt sind aus einer Einzelbindung, *-N[(L6)b6-(R6)]-*', *-B(R6)-*', *-P(R6)-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-Ge(R6)(R7)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R6)=C(R7)-*', *-C(=S)-*' und *-C≡C-*',
L6 ausgewählt ist aus einer Einzelbindung, einer substituierten oder unsubstituierten carbocyclischen C5-C30-Gruppe, und einer substituierten oder unsubstituierten heterocyclischen C1-C30-Gruppe,
b6 ausgewählt ist aus 1 bis 3, wobei dann, wenn b6 zwei oder mehr ist, zwei oder mehr Gruppen von L6 identisch zueinander oder voneinander verschieden sind,
R6 und R7 gegebenenfalls über eine erste Verknüpfungsgruppe verknüpft sind, um eine substituierte oder unsubstituierte carbocyclische C5-C30-Gruppe oder eine substituierte oder unsubstituierte heterocyclische C1-C30-Gruppe zu bilden,
R1 bis R7 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, -SF5, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer substituierten oder unsubstituierten C1-C60-Alkylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkenylgruppe, einer substituierten oder unsubstituierten C2-C60-Alkinylgruppe, einer substituierten oder unsubstituierten C1-C60-Alkoxygruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkylgruppe, einer substituierten oder unsubstituierten C3-C10-Cycloalkenylgruppe, einer substituierten oder unsubstituierten C1-C10-Heterocycloalkenylgruppe, einer substituierten oder unsubstituierten C6-C60-Arylgruppe, einer substituierten oder unsubstituierten C6-C60-Aryloxygruppe, einer substituierten oder unsubstituierten C6-C60-Arylthiogruppe, einer substituierten oder unsubstituierten C7-C60-Arylalkylgruppe, 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 C2-C60-Heteroarylalkylgruppe, einer substituierten oder unsubstituierten einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer substituierten oder unsubstituierten einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), - B(Q6)(Q7) und -P(=O)(Q8)(Q9),
a1 bis a5 jeweils unabhängig für 0, 1, 2, 3, 4 oder 5 stehen,
zwei der Gruppen R1 in der Zahl von a1, der Gruppen R2 in der Zahl von a2, der Gruppen R3 in der Zahl von a3, der Gruppen R4 in der Zahl von a4 und der Gruppen R5 in der Zahl von a5 gegebenenfalls verknüpft sind, um eine substituierte oder unsubstituierte carbocyclische C5-C30-Gruppe oder eine substituierte oder unsubstituierte heterocyclische C1-C30-Gruppe zu bilden,
mindestens ein Substituent der substituierten carbocyclischen C5-C30-Gruppe, der substituierten heterocyclischen C1-C30-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 C7-C60-Arylalkylgruppe, der substituierten C1-C60-Heteroarylgruppe, der substituierten C1-C60-Heteroaryloxygruppe, der substituierten C1-C60-Heteroarylthiogruppe, der substituierten C2-C60-Heteroarylalkylgruppe, der substituierten einwertigen nichtaromatischen kondensierten polycyclischen Gruppe und der substituierten einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe ausgewählt ist aus:
Deuterium, -F, Cl, -Br, -I, -CD3, -CD2H, -CDH2, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe und einer C1-C60-Alkoxygruppe;
einerC1-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, -CD3, -CD2H, -CDH2, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C7-C60-Arylalkylgruppe, einer C1-C60-Heteroarylgruppe, einer C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer C2-C60-Heteroarylalkylgruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, -N(Q11)(Q12), -Si(Q13)(Q14)(Q15), -B(Q16)(Q17) und -P(=O)(Q18)(Q19),
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 C7-C60-Arylalkylgruppe, einer C1-C60-Heteroarylgruppe, einer C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer C2-C60-Heteroarylalkylgruppe, 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 C7-C60-Arylalkylgruppe, einer C1-C60-Heteroarylgruppe, einer C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer C2-C60-Heteroarylalkylgruppe, 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, -CD3, - CD2H, -CDH2, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe, einer C1-C60-Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C7-C60-Arylalkylgruppe, einer C1-C60-Heteroarylgruppe, einer C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer C2-C60-Heteroarylalkylgruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe, einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25), -B(Q26)(Q27) und -P(=O)(Q28)(Q29); und
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35), -B(Q36)(Q37) und -P(=O)(Q38)(Q39), und
Q1 bis Q9, Q11 bis Q19, Q21 bis Q29 und Q31 bis Q39 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C60-Alkylgruppe, einer C2-C60-Alkenylgruppe, einer C2-C60-Alkinylgruppe, einer C1-C60-Alkoxygruppe, einer C3-C10-Cycloalkylgruppe, einer C1-C10-Heterocycloalkylgruppe, einer C3-C10-Cycloalkenylgruppe, einer C1-C10-Heterocycloalkenylgruppe, einer C6-C60-Arylgruppe, einer C6-C60-Arylgruppe substituiert durch mindestens eines ausgewählt aus einer C1-C60-Alkylgruppe und einer C6-C60-Arylgruppe, einer C6-C60-Aryloxygruppe, einer C6-C60-Arylthiogruppe, einer C7-C60-Arylalkylgruppe, einer C1-C60-Heteroarylgruppe, einer C1-C60-Heteroaryloxygruppe, einer C1-C60-Heteroarylthiogruppe, einer C2-C60-Heteroarylalkylgruppe, einer einwertigen nichtaromatischen kondensierten polycyclischen Gruppe und einer einwertigen nichtaromatischen kondensierten heteropolycyclischen Gruppe.
M für Pt steht.
X1 bis X3 jeweils für N stehen, eine Bindung zwischen X1 und M und eine Bindung zwischen X3 und M jeweils eine koordinative Bindung ist und eine Bindung zwischen X2 und M eine kovalente Bindung ist;
X1 und X3 jeweils für N stehen, X2 für C steht, eine Bindung zwischen X1 und M und eine Bindung zwischen X3 und M jeweils eine koordinative Bindung ist und eine Bindung zwischen X2 und M eine kovalente Bindung ist; oder
X2 und X3 jeweils für N stehen, X1 für C steht, eine Bindung zwischen X2 und M und eine Bindung zwischen X3 und M jeweils eine koordinative Bindung ist und eine Bindung zwischen X1 und M eine kovalente Bindung ist.
Cy1 bis Cy5 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 Pyrrolgruppe, einer Thiophengruppe, einer Furangruppe, einer Indolgruppe, einer iso-Indolgruppe, einer Benzoborolgruppe, einer Benzophospholgruppe, einer Indengruppe, einer Benzosilolgruppe, einer Benzogermolgruppe, einer Benzothiophengruppe, einer Benzoselenophengruppe, einer Benzofurangruppe, einer Carbazolgruppe, einer Dibenzoborolgruppe, einer Dibenzophospholgruppe, einer Fluorengruppe, einer Dibenzosilolgruppe, einer Dibenzogermolgruppe, einer Dibenzothiophengruppe, einer Dibenzoselenophengruppe, einer Dibenzofurangruppe, einer Dibenzothiophen-5-oxid-Gruppe, einer 9H-Fluoren-9-on-Gruppe, einer Dibenzothiophen-5,5-dioxid-Gruppe, einer Azacarbazolgruppe, einer Azadibenzoborolgruppe, einer Azadibenzophospholgruppe, einer Azafluorengruppe, einer Azadibenzosilolgruppe, einer Azadibenzogermolgruppe, einer Azadibenzothiophengruppe, einer Azadibenzoselenophengruppe, einer Azadibenzofurangruppe, einer Azadibenzothiophen-5-oxid-Gruppe, einer Aza-9H-fluoren-9-on-Gruppe, einer Azadibenzothiophen-5,5-dioxid-Gruppe, einer Pyridingruppe, einer Pyrimidingruppe, einer Pyrazingruppe, einer Pyridazingruppe, einer Triazingruppe, einer Chinolingruppe, einer Isochinolingruppe, einer Chinoxalingruppe, einer Chinazolingruppe, einer Phenanthrolingruppe, einer Pyrazolgruppe, einer Imidazolgruppe, einer Triazolgruppe, einer Tetrazolgruppe, einer Oxazolgruppe, einer Isoxazolgruppe, einer Thiazolgruppe, einer Isothiazolgruppe, einer Oxadiazolgruppe, einer Thiadiazolgruppe, einer Benzopyrazolgruppe, einer Benzimidazolgruppe, einer Benzoxazolgruppe, einer Benzothiazolgruppe, einer Benzooxadiazolgruppe, einer Benzothiadiazolgruppe, einer 5,6,7,8-Tetrahydroisochinolingruppe und einer 5,6,7,8-Tetrahydrochinolingruppe;
wobei vorzugsweise
Cy1 bis Cy5 jeweils unabhängig ausgewählt sind aus einer Benzolgruppe, einer Naphthalingruppe, einer Indolgruppe, einer iso-Indolgruppe, einer Dibenzothiophengruppe, einer Dibenzofurangruppe, einer Azadibenzothiophengruppe, einer Azadibenzofurangruppe, einer Pyridingruppe, einer Pyrimidingruppe, einer Pyrazingruppe, einer Pyridazingruppe, einer Chinolingruppe, einer Isochinolingruppe, einer Pyrazolgruppe und einer Imidazolgruppe oder einer Benzimidazolgruppe.
R1 bis R7 jeweils unabhängig ausgewählt sind aus:
Wasserstoff, Deuterium, -F, -Cl, -Br, -I, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, -SF5, einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe;
einer C1-C20-Alkylgruppe und einer C1-C20-Alkoxygruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C10-Alkylgruppe, einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Pyridinylgruppe und einer Pyrimidinylgruppe;
einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Chinoxalinylgruppe, einer Chinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Azadibenzofuranylgruppe und einer Azadibenzothiophenylgruppe;
einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Chinoxalinylgruppe, einer Chinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Azadibenzofuranylgruppe und einer Azadibenzothiophenylgruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, einer Hydroxylgruppe, einer Cyanogruppe, einer Nitrogruppe, einer Aminogruppe, einer Amidinogruppe, einer Hydrazingruppe, einer Hydrazongruppe, einer Carbonsäuregruppe oder einem Salz davon, einer Sulfonsäuregruppe oder einem Salz davon, einer Phosphorsäuregruppe oder einem Salz davon, einer C1-C20-Alkylgruppe, einer C1-C20-Alkoxygruppe, einer Cyclopentylgruppe, einer Cyclohexylgruppe, einer Cycloheptylgruppe, einer Cyclooctylgruppe, einer Adamantanylgruppe, einer Norbornanylgruppe, einer Norbornenylgruppe, einer Cyclopentenylgruppe, einer Cyclohexenylgruppe, einer Cycloheptenylgruppe, einer Phenylgruppe, einer Naphthylgruppe, einer Fluorenylgruppe, einer Phenanthrenylgruppe, einer Anthracenylgruppe, einer Fluoranthenylgruppe, einer Triphenylenylgruppe, einer Pyrenylgruppe, einer Chrysenylgruppe, einer Pyrrolylgruppe, einer Thiophenylgruppe, einer Furanylgruppe, einer Imidazolylgruppe, einer Pyrazolylgruppe, einer Thiazolylgruppe, einer Isothiazolylgruppe, einer Oxazolylgruppe, einer Isoxazolylgruppe, einer Pyridinylgruppe, einer Pyrazinylgruppe, einer Pyrimidinylgruppe, einer Pyridazinylgruppe, einer Isoindolylgruppe, einer Indolylgruppe, einer Indazolylgruppe, einer Purinylgruppe, einer Chinolinylgruppe, einer Isochinolinylgruppe, einer Benzochinolinylgruppe, einer Chinoxalinylgruppe, einer Chinazolinylgruppe, einer Cinnolinylgruppe, einer Carbazolylgruppe, einer Phenanthrolinylgruppe, einer Benzimidazolylgruppe, einer Benzofuranylgruppe, einer Benzothiophenylgruppe, einer Isobenzothiazolylgruppe, einer Benzoxazolylgruppe, einer Isobenzoxazolylgruppe, einer Triazolylgruppe, einer Tetrazolylgruppe, einer Oxadiazolylgruppe, einer Triazinylgruppe, einer Dibenzofuranylgruppe, einer Dibenzothiophenylgruppe, einer Benzocarbazolylgruppe, einer Dibenzocarbazolylgruppe, einer Imidazopyridinylgruppe, einer Imidazopyrimidinylgruppe, einer Azadibenzofuranylgruppe und einer Azadibenzothiophenylgruppe; und
-N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7) und -P(=O)(Q8)(Q9), und
Q1 bis Q9 jeweils unabhängig ausgewählt sind aus:
-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, - CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CH3, -CD2CD2H und - CD2CDH2;
einer n-Propylgruppe, einer iso-Propylgruppe, einer n-Butylgruppe, einer Isobutylgruppe, einer sec-Butylgruppe, einer tert-Butylgruppe, einer n-Pentylgruppe, einer Isopentylgruppe, einer sec-Pentylgruppe, einer tert-Pentylgruppe, einer Phenylgruppe und einer Naphthylgruppe; und
einer n-Propylgruppe, einer iso-Propylgruppe, einer n-Butylgruppe, einer Isobutylgruppe, einer sec-Butylgruppe, einer tert-Butylgruppe, einer n-Pentylgruppe, einer Isopentylgruppe, einer sec-Pentylgruppe, einer tert-Pentylgruppe, einer Phenylgruppe und einer Naphthylgruppe, jeweils substituiert durch mindestens eines ausgewählt aus Deuterium, einer C1-C10-Alkylgruppe und einer Phenylgruppe;
wobei vorzugsweise
R1 bis R7 jeweils unabhängig ausgewählt sind aus Wasserstoff, Deuterium, -F, einer Cyanogruppe, einer Nitrogruppe, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Gruppen, die von den Formeln 9-1 bis 9-22 dargestellt werden, Gruppen, die von den Formeln 10-1 bis 10-144 dargestellt werden, und -Si(Q3)(Q4)(Q5):
wobei in den Formeln 9-1 bis 9-22 und 10-1 bis 10-144 i-Pr eine Isopropylgruppe angibt, i-Bu eine Isobutylgruppe angibt, t-Bu eine tert-Butylgruppe angibt, TMS eine Trimethylsilylgruppe angibt, Ph eine Phenylgruppe angibt und * eine Bindungsstelle zu einem benachbarten Atom angibt.
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus
Gruppen, die von den Formeln Cy1-1 bis Cy1-39 dargestellt werden:
wobei in den Formeln Cy1-1 bis Cyl-39
X1 und R1 dieselben wie in Anspruch 1 beschrieben sind,
X11 für O, S, N(R11) oder C(R11)(R12) steht,
X19 für C(R19) oder N steht,
R11 bis R19 dieselben wie im Zusammenhang mit R1 in Anspruch 1 beschrieben sind,
a13 für eine ganze Zahl von 0 bis 3 steht,
a14 für eine ganze Zahl von 0 bis 4 steht, und
*, *' und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben; und/oder
wobei
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cy2-1 bis Cy2-39 dargestellt werden:
wobei in den Formeln Cy2-1 bis Cy2-39
X2 und R2 dieselben wie in Anspruch 1 beschrieben sind,
X21 für O, S, N(R21), oder C(R21)(R22) steht,
X29 für C(R29) oder N steht,
R21 bis R29 dieselben wie im Zusammenhang mit R2 in Anspruch 1 beschrieben sind,
a23 für eine ganze Zahl von 0 bis 3 steht,
a24 für eine ganze Zahl von 0 bis 4 steht, und
*, *' und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben; und/oder
wobei
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cy3-1 bis Cy3-39 dargestellt werden:
wobei in den Formeln Cy3-1 bis Cy3-39
X3 und R3 dieselben wie in Anspruch 1 beschrieben sind,
X31 für O, S, N(R31), oder C(R31)(R32) steht,
X39 für C(R39) oder N steht,
R31 bis R39 dieselben wie im Zusammenhang mit R3 in Anspruch 1 beschrieben sind,
a33 für eine ganze Zahl von 0 bis 3 steht,
a34 für eine ganze Zahl von 0 bis 4 steht, und
*, *' und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben; und/oder wobei
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cz-1 bis Cz-27 dargestellt werden:
wobei in den Formeln Cz-1 bis Cz-27
R4 und R5 dieselben wie in Anspruch 1 beschrieben sind,
a42 und a52 jeweils unabhängig für eine ganze Zahl von 0 bis 2 stehen,
a43 und a53 jeweils unabhängig für eine ganze Zahl von 0 bis 3 stehen,
a45 und a55 jeweils unabhängig für eine ganze Zahl von 0 bis 5 stehen, und
*, *' und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben.
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cy1(1) bis Cy1(26) dargestellt werden,
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cy2(1) bis Cy2(15) dargestellt werden,
ein in Formel 1 von
dargestellter Rest ausgewählt ist aus Gruppen, die von den Formeln Cy3(1) bis Cy3(26) dargestellt werden, und
ein in Formel 1 von
dargestellter Rest ausgewählt ist
aus Gruppen, die von den Formeln Cz(1) bis Cz(21) dargestellt werden:
wobei in den Formeln Cy1(1) bis Cy1(26), Cy2(1) bis Cy2(15), Cy3(1) bis Cy3(26) und Cz(1) bis Cz(21)
X1 bis X3 und R1 bis R5 dieselben wie in Anspruch 1 beschrieben sind,
X11 für O, S, N(R11) oder C(R11)(R12) steht,
X21 für O, S, N(R21), oder C(R21)(R22) steht,
X31 für O, S, N(R31), oder C(R31)(R32) steht,
R1a bis R1c, R11 und R12 dieselben wie im Zusammenhang mit R1 in Anspruch 1 beschrieben sind,
R2a bis R2c, R21 und R22 dieselben wie im Zusammenhang mit R2 in Anspruch 1 beschrieben sind,
R3a bis R3c, R31 und R32 dieselben wie im Zusammenhang mit R3 in Anspruch 1 beschrieben sind,
R1, R1a bis R1c, R2, R2a bis R2c, R3, R3a bis R3c, R4 und R5 nicht für Wasserstoff stehen, und
*, *' und *" jeweils eine Bindungsstelle zu einem benachbarten Atom angeben.
wobei in den Formeln 1-1 bis 1-32
M, X1 bis X3 und R1 bis R5 dieselben wie in Anspruch 1 beschrieben sind,
X11 für O, S, N(R11) oder C(R11)(R12) steht,
X21 für O, S, N(R21) oder C(R21)(R22) steht,
X31 für O, S, N(R31) oder C(R31)(R32) steht,
R1a, R1b, R11 und R12 dieselben wie im Zusammenhang mit R1 in Anspruch 1 beschrieben sind,
R2a, R2b, R21 und R22 dieselben wie im Zusammenhang mit R2 in Anspruch 1 beschrieben sind, und
R3a, R3b, R31 und R32 dieselben wie im Zusammenhang mit R3 in Anspruch 1 beschrieben sind.
eine erste Elektrode;
eine zweite Elektrode; und
eine organische Schicht, die zwischen der ersten Elektrode und der zweiten Elektrode angeordnet ist,
wobei die organische Schicht eine Emissionsschicht umfasst, und
wobei die organische Schicht mindestens eine organometallische Verbindung nach einem der Ansprüche 1 bis 10 umfasst.
die erste Elektrode eine Anode ist,
die zweite Elektrode eine Kathode ist,
die organische Schicht ferner einen Lochtransportbereich, der zwischen der ersten Elektrode und der Emissionsschicht angeordnet ist, und einen Elektronentransportbereich, der zwischen der Emissionsschicht und der zweiten Elektrode angeordnet ist, umfasst,
wobei der Lochtransportbereich eine Lochinjektionsschicht, eine Lochtransportschicht, eine Elektronenblockierschicht oder eine beliebige Kombination davon umfasst, und
wobei der Elektronentransportbereich eine Lochblockierschicht, eine Elektronentransportschicht, eine Elektroneninjektionsschicht oder eine beliebige Kombination davon umfasst.
die Emissionsschicht ferner einen Wirt umfasst, und
eine Menge des Wirts größer ist als eine Menge der organometallischen Verbindung.
où, dans la Formule 1,
M est Pt ou Pd,
X1 à X3 sont chacun indépendamment C ou N,
deux liaisons choisies parmi une liaison entre X1 et M, une liaison entre X2 et M, et une liaison entre X3 et M sont chacune une liaison de coordination, et l'autre est une liaison covalente,
Cy1 à Cy5 sont chacun indépendamment choisis entre un groupe carbocyclique C5-C30 et un groupe hétérocylique C1-C30,
T1 et T2 sont chacun indépendamment choisis parmi une liaison simple, *-N[(L6)b6-(R6)]-*', *-B(R6)-*', *-P(R6)-*', *-C(R6)(R7)-*', *-Si(R6)(R7)-*', *-Ge(R6)(R7)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R6)=C(R7)-*', *-C(=S)-*', et *-C≡C-*',
L6 est choisi parmi une liaison simple, un groupe carbocyclique C5-C30 substitué ou non substitué, et un groupe hétérocyclique C1-C30 substitué ou non substitué,
b6 est choisi parmi 1 à 3, où, quand b6 est au moins deux, deux groupes L6 ou plus sont identiques ou différents l'un de l'autre,
R6 et R7 sont éventuellement liés par l'intermédiaire d'un premier groupe de liaison pour former un groupe carbocyclique C5-C30 substitué ou non substitué ou un groupe hétérocyclique C1-C30 substitué ou non substitué,
R1 à R7 sont chacun indépendamment choisis parmi hydrogène, deutérium, -F, -Cl, - Br, - I, -SF5, groupe hydroxyle, groupe cyano, groupe nitro, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou un sel de celui-ci, groupe acide sulfonique ou un sel de celui-ci, groupe acide phosphorique ou un sel de celui-ci, groupe alkyle C1-C60 substitué ou non substitué, groupe alkényle C2-C60 substitué ou non substitué, groupe alkynyle C2-C60 substitué ou non substitué, groupe alkoxy C1-C60 substitué ou non substitué, groupe cycloalkyle C3-C10 substitué ou non substitué, groupe hétérocycloalkyle C1-C10 substitué ou non substitué, groupe cycloalkényle C3-C10 substitué ou non substitué, groupe hétérocycloalkényle C1-C10 substitué ou non substitué, groupe aryle C6-C60 substitué ou non substitué, groupe aryloxy C6-C60 substitué ou non substitué, groupe arylthio C6-C60 substitué ou non substitué, groupe arylalkyle C7-C60 substitué ou non substitué, groupe hétéroaryle C1-C60 substitué ou non substitué, groupe hétéroaryloxy C1-C60 substitué ou non substitué, groupe hétéroarylthio C1-C60 substitué ou non substitué, groupe hétéroarylalkyle C2-C60 substitué ou non substitué, groupe polycyclique condensé non aromatique monovalent substitué ou non substitué, groupe hétéropolycyclique condensé non aromatique monovalent substitué ou non substitué, - N(Q1)(Q2), -Si(Q3)(Q4)(Q5), - B(Q6)(Q7), et -P(=O)(Q8)(Q9),
a1 à a5 sont chacun indépendamment 0, 1, 2, 3, 4, ou 5,
deux des groupes R1 dans le nombre de a1, groupes R2 dans le nombre de a2, groupes R3 dans le nombre de a3, groupes R4 dans le nombre de a4, et groupes R5 dans le nombre de a5 sont éventuellement liés pour former un groupe carbocyclique C5-C30 substitué ou non substitué, ou un groupe hétérocyclique C1-C30 substitué ou non substitué,
au moins un substituant du groupe carbocyclique C5-C30 substitué, groupe hétérocyclique C1-C30 substitué, groupe alkyle C1-C60 substitué, groupe alkényle C2-C60 substitué, groupe alkynyle C2-C60 substitué, groupe alkoxy C1-C60 substitué, groupe cycloalkyle C3-C10 substitué, groupe hétérocycloalkyle C1-C10 substitué, the groupe cycloalkényle C3-C10 substitué, groupe hétérocycloalkényle C1-C10 substitué, groupe aryle C6-C60 substitué, groupe aryloxy C6-C60 substitué, groupe arylthio C6-C60 substitué, groupe arylalkyle C7-C60 substitué, groupe hétéroaryle C1-C60 substitué, groupe hétéroaryloxy C1-C60 substitué, groupe hétéroarylthio C1-C60 substitué, groupe hétéroarylalkyle C2-C60 substitué, groupe polycyclique condensé non aromatique monovalent substitué, et groupe hétéropolycyclique condensé non aromatique substitué est choisi parmi :
deutérium, -F, Cl, -Br, -I, -CD3, -CD2H, -CDH2, groupe hydroxyle, groupe cyano, groupe nitro, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou un sel de celui-ci, groupe acide sulfonique ou un sel de celui-ci, groupe acide phosphorique ou un sel de celui-ci, groupe alkyle C1-C60, groupe alkényle C2-C60, groupe alkynyle C2-C60, et groupe alkoxy C1-C60 ;
groupe alkyle C1-C60, groupe alkényle C2-C60, groupe alkynyle C2-C60, et groupe alkoxy C1-C60, chacun étant substitué par au moins un élément choisi parmi deutérium, -F, -Cl, -Br, -I, - CD3, -CD2H, -CDH2, groupe hydroxyle, groupe cyano, groupe nitro, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou un sel de celui-ci, groupe acide sulfonique ou un sel de celui-ci, groupe acide phosphorique ou un sel de celui-ci, groupe cycloalkyle C3-C10, groupe hétérocycloalkyle C1-C10, groupe cycloalkényle C3-C10, groupe hétérocycloalkényle C1-C10, groupe aryle C6-C60, groupe aryloxy C6-C60, groupe arylthio C6-C60, groupe arylalkyle C7-C60, groupe hétéroaryle C1-C60, groupe hétéroaryloxy C1-C60, groupe hétéroarylthio C1-C60, groupe hétéroarylalkyle C2-C60, groupe polycyclique condensé non aromatique monovalent, groupe hétéropolycyclique condensé non aromatique, -N(Q11)(Q12), - Si(Q13)(Q14)(Q15), -B(Q16)(Q17), et -P(=O)(Q18)(Q19);
groupe cycloalkyle C3-C10, groupe hétérocycloalkyle C1-C10, groupe cycloalkényle C3-C10, groupe hétérocycloalkényle C1-C10, groupe aryle C6-C60, groupe aryloxy C6-C60, groupe arylthio C6-C60, groupe arylalkyle C7-C60, groupe hétéroaryle C1-C60, groupe hétéroaryloxy C1-C60, groupe hétéroarylthio C1-C60, groupe hétéroarylalkyle C2-C60, groupe polycyclique condensé non aromatique monovalent, et groupe hétéropolycyclique condensé non aromatique monovalent ;
groupe cycloalkyle C3-C10, groupe hétérocycloalkyle C1-C10, groupe cycloalkényle C3-C10, groupe hétérocycloalkényle C1-C10, groupe aryle C6-C60, groupe aryloxy C6-C60, groupe arylthio C6-C60, groupe arylalkyle C7-C60, groupe hétéroaryle C1-C60, groupe hétéroaryloxy C1-C60, groupe hétéroarylthio C1-C60, groupe hétéroarylalkyle C2-C60, groupe polycyclique condensé non aromatique monovalent, et groupe hétéropolycyclique condensé non aromatique monovalent, chacun étant substitué par au moins un élément choisi parmi deutérium, -F, -Cl, -Br, -I, -CD3, - CD2H, -CDH2, groupe hydroxyle, groupe cyano, groupe nitro, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou un sel de celui-ci, groupe acide sulfonique ou un sel de celui-ci , groupe acide phosphorique ou un sel de celui-ci, groupe alkyle C1-C60, groupe alkényle C2-C60, groupe alkynyle C2-C60, groupe alkoxy C1-C60, groupe cycloalkyle C3-C10, groupe hétérocycloalkyle C1-C10, groupe cycloalkényle C3-C10, groupe hétérocycloalkényle C1-C10, groupe aryle C6-C60, groupe aryloxy C6-C60, groupe arylthio C6-C60, groupe arylalkyle C7-C60, groupe hétéroaryle C1-C60, groupe hétéroaryloxy C1-C60,, groupe hétéroarylthio C1-C60, groupe hétéroarylalkyle C2-C60, groupe polycyclique condensé non aromatique monovalent, groupe hétéropolycyclique condensé non aromatique monovalent, -N(Q21)(Q22), -Si(Q23)(Q24)(Q25), - B(Q26)(Q27), et -P(=O)(Q28)(Q29) ; et
-N(Q31)(Q32), -Si(Q33)(Q34)(Q35), -B(Q36)(Q37), et -P(=O)(Q38)(Q39), et
Q1 à Q9, Q11 à Q19, Q21 à Q29, et Q31 à Q39 sont chacun indépendamment choisis parmi hydrogène, deutérium, -F, -Cl, -Br, -I, groupe hydroxyle, groupe cyano, groupe nitro, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou sel de celui-ci, groupe acide sulfonique ou sel de celui-ci, groupe acide phosphorique ou sel de celui-ci, groupe alkyle C1-C60, groupe alkényle C2-C60, groupe alkynyle C2-C60, groupe alkoxy C1-C60, groupe cycloalkyle C3-C10, groupe hétérocycloalkyle C1-C10, groupe cycloalkényle C3-C10, groupe hétérocycloalkényle C1-C10, groupe aryle C6-C60, groupe aryle C6-C60 substitué par au moins un élément choisi parmi groupe alkyle C1-C60 et groupe aryle C6-C60, groupe aryloxy C6-C60, groupe arylthio C6-C60, groupe arylalkyle C7-C60, groupe hétéroaryle C1-C60, groupe hétéroaryloxy C1-C60, groupe hétéroarylthio C1-C60, groupe hétéroarylalkyle C2-C60, groupe polycyclique condensé non aromatique monovalent, et groupe hétéropolycyclique condensé non aromatique monovalent.
M est Pt.
X1 à X3 sont chacun N, une liaison entre X1 et M et une liaison entre X3 et M sont chacune une liaison de coordination, et une liaison entre X2 et M est une liaison covalente ;
X1 et X3 sont chacun N, X2 est C, une liaison entre X1 et M et une liaison entre X3 et M sont chacune une liaison de coordination, et une liaison entre X2 et M est une liaison covalente ; ou
X2 et X3 sont chacun N, X1 est C, une liaison entre X2 et M et une liaison entre X3 et M sont chacune une liaison de coordination, et une liaison entre X1 et M est une liaison covalente.
Cy1 à Cy5 sont chacun indépendamment choisis parmi groupe benzène, groupe naphthalène, groupe anthracène, groupe phénanthrène, groupe triphénylène, groupe pyrène, groupe chrysène, groupe cyclopentadiène, groupe 1,2,3,4- tétrahydronaphthalène, groupe pyrrole, groupe thiophène, groupe furane, groupe indole, groupe iso-indole, groupe benzoborole, groupe benzophosphole, groupe indène, groupe benzosilole, groupe benzogermole, groupe benzothiophène, groupe benzosélénophène, groupe benzofurane, groupe carbazole, groupe dibenzoborole, groupe dibenzophosphole, groupe fluorène, groupe dibenzosilole, groupe dibenzogermole, groupe dibenzothiophène, groupe dibenzosélénophène, groupe dibenzofurane, groupe dibenzothiophène 5-oxyde, groupe 9H-fluorène-9-one, groupe dibenzothiophène 5,5-dioxyde, groupe azacarbazole, groupe azadibenzoborole, groupe azadibenzophosphole, groupe azafluorène, groupe azadibenzosilole, groupe azadibenzogermole, groupe azadibenzothiophène, groupe azadibenzosélénophène, groupe azadibenzofurane, groupe azadibenzothiophène 5-oxyde, groupe aza-9H-fluorène-9-one, groupe azadibenzothiophène 5,5-dioxyde, groupe pyridine, groupe pyrimidine, groupe pyrazine, groupe pyridazine, groupe triazine, groupe quinoline, groupe isoquinoline, groupe quinoxaline, groupe quinazoline, groupe phenanthroline, groupe pyrazole, groupe imidazole, groupe triazole, groupe tetrazole, groupe oxazole, groupe isoxazole, groupe thiazole, groupe isothiazole, groupe oxadiazole, groupe thiadiazole, groupe benzopyrazole, groupe benzimidazole, groupe benzoxazole, groupe benzothiazole, groupe benzooxadiazole, groupe benzothiadiazole, groupe 5,6,7,8- tetrahydroisoquinoline, et groupe 5,6,7,8-tetrahydroquinoline ;
de préférence dans lequel
Cy1 à Cy5 sont chacun indépendamment choisis parmi groupe benzène, groupe naphthalène, groupe indole, groupe iso-indole, groupe dibenzothiophène, groupe dibenzofurane, groupe azadibenzothiophène, groupe azadibenzofurane, groupe pyridine, groupe pyrimidine, groupe pyrazine, groupe pyridazine, groupe quinoline, groupe isoquinoline, groupe pyrazole, et groupe imidazole ou groupe benzimidazole.
hydrogène, deutérium, -F, -Cl, -Br, -I, groupe hydroxyle, groupe cyano, groupe nitro, groupe amino, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou un sel de celui-ci, groupe acide sulfonique ou un sel de celui-ci, groupe acide phosphorique ou un sel de celui-ci, -SF5, groupe alkyle C1-C20, et groupe alkoxy C1-C20 ;
groupe alkyle C1-C20 et groupe alkoxy C1-C20, chacun étant substitué par au moins un élément choisi parmi deutérium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groupe hydroxyle, groupe cyano, groupe nitro, groupe amino, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou sel de celui-ci, groupe acide sulfonique ou sel de celui-ci, groupe acide phosphorique ou sel de celui-ci, groupe alkyle C1-C10, groupe cyclopentyle, groupe cyclohexyle, groupe cycloheptyle, groupe cyclooctyle, groupe adamantanyle, groupe norbornanyle, groupe norbornényle, groupe cyclopentényle, groupe cyclohexényle, groupe cycloheptényle, groupe phényle, groupe naphthyle, groupe pyridinyle, et groupe pyrimidinyle ;
groupe cyclopentyle, groupe cyclohexyle, groupe cycloheptyle, groupe cyclooctyle, groupe adamantanyle, groupe norbornanyle, groupe norbornenyle, groupe cyclopentenyle, groupe cyclohexényle, groupe cycloheptényle, groupe phényle, groupe naphthyle, groupe fluorényle, groupe phénanthrényle, groupe anthracényle, groupe fluoranthényle, groupe triphénylényle, groupe pyrényle, groupe chrysényle, groupe pyrrolyle, groupe thiophényle, groupe furanyle, groupe imidazolyle, groupe pyrazolyle, groupe thiazolyle, groupe isothiazolyle, groupe oxazolyle, groupe isoxazolyle, groupe pyridinyle, groupe pyrazinyle, groupe pyrimidinyle, groupe pyridazinyle, groupe isoindolyle, groupe indolyle, groupe indazolyle, groupe purinyle, groupe quinolinyle, groupe isoquinolinyle, groupe benzoquinolinyle, groupe quinoxalinyle, groupe quinazolinyle, groupe cinnolinyle, groupe carbazolyle, groupe phénanthrolinyle, groupe benzimidazolyle, groupe benzofuranyle, groupe benzothiophényle, groupe isobenzothiazolyle, groupe benzoxazolyle, groupe isobenzoxazolyle, groupe triazolyle, groupe tétrazolyle, groupe oxadiazolyle, groupe triazinyle, groupe dibenzofuranyle, groupe dibenzothiophényle, groupe benzocarbazolyle, groupe dibenzocarbazolyle, groupe imidazopyridinyle, groupe imidazopyrimidinyle, groupe azadibenzofuranyle, et groupe azadibenzothiophényle ;
groupe cyclopentyle, groupe cyclohexyle, groupe cycloheptyle, groupe cyclooctyle, groupe adamantanyle, groupe norbornanyle, groupe norbornényle, groupe cyclopentényle, groupe cyclohexényle, groupe cycloheptényle, groupe phényle, groupe naphthyle, groupe fluorényle, groupe phénanthrényle, groupe anthracényle, groupe fluoranthényle, groupe triphénylényle, groupe pyrényle, groupe chrysényle, groupe pyrrolyle, groupe thiophényle, groupe furanyle, groupe imidazolyle, groupe pyrazolyle, groupe thiazolyle, groupe isothiazolyle, groupe oxazolyle, groupe isoxazolyle, groupe pyridinyle, groupe pyrazinyle, groupe pyrimidinyle, groupe pyridazinyle, groupe isoindolyle, groupe indolyle, groupe indazolyle, groupe purinyle, groupe quinolinyle, groupe isoquinolinyle, groupe benzoquinolinyle, groupe quinoxalinyle, groupe quinazolinyle, groupe cinnolinyle, groupe carbazolyle, groupe phénanthrolinyle, groupe benzimidazolyle, groupe benzofuranyle, groupe benzothiophényle, groupe isobenzothiazolyle, groupe benzoxazolyle, groupe isobenzoxazolyle, groupe triazolyle, groupe tétrazolyle, groupe oxadiazolyle, groupe triazinyle, groupe dibenzofuranyle, groupe dibenzothiophényle, groupe benzocarbazolyle, groupe dibenzocarbazolyle, groupe imidazopyridinyle, groupe imidazopyrimidinyle, groupe azadibenzofuranyle, et groupe azadibenzothiophényle, chacun étant substitué par au moins un élément choisi parmi deutérium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groupe hydroxyle, groupe cyano, groupe nitro, groupe amino, groupe amidino, groupe hydrazine, groupe hydrazone, groupe acide carboxylique ou sel de celui-ci, groupe acide sulfonique ou sel de celui-ci, groupe acide phosphorique ou sel de celui-ci, groupe alkyle C1-C20, groupe alkoxy C1-C20, groupe cyclopentyle, groupe cyclohéxyle, groupe cycloheptyle, groupe cyclooctyle, groupe adamantanyle, groupe norbornanyle, groupe norbornenyle, groupe cyclopentényle, groupe cyclohexényle, groupe cycloheptényle, groupe phényle, groupe naphthyle, groupe fluorényle, groupe phénanthrényle, groupe anthracényle, groupe fluoranthényle, groupe triphénylényle, groupe pyrényle, groupe chrysényle, groupe pyrrolyle, groupe thiophényle, groupe furanyle, groupe imidazolyle, groupe pyrazolyle, a groupe thiazolyle, groupe isothiazolyle, groupe oxazolyle, groupe isoxazolyle, groupe pyridinyle, groupe pyrazinyle, groupe pyrimidinyle, groupe pyridazinyle, groupe isoindolyle, groupe indolyle, groupe indazolyle, groupe purinyle, groupe quinolinyle, groupe isoquinolinyle, groupe benzoquinolinyle, groupe quinoxalinyle, groupe quinazolinyle, groupe cinnolinyle, groupe carbazolyle, groupe phénanthrolinyle, groupe benzimidazolyle, groupe benzofuranyle, groupe benzothiophényle, groupe isobenzothiazolyle, groupe benzoxazolyle, groupe isobenzoxazolyle, groupe triazolyle, groupe tetrazolyle, groupe oxadiazolyle, groupe triazinyle, groupe dibenzofuranyle, groupe dibenzothiophényle, groupe benzocarbazolyle, groupe dibenzocarbazolyle, groupe imidazopyridinyle, groupe imidazopyrimidinyle, groupe azadibenzofuranyle, et groupe azadibenzothiophényle ; et
-N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), et -P(=O)(Q8)(Q9), et
Q1 à Q9 sont chacun indépendamment choisis parmi :
-CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, - CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CH3, -CD2CD2H, et -CD2CDH2 ;
groupe n-propyle, groupe iso-propyle, groupe n-butyle, groupe isobutyle, groupe sec-butyle, groupe tert-butyle, groupe n-pentyle, groupe isopentyle, groupe sec- pentyle, groupe tert-pentyle, groupe phényle, et groupe naphthyle ; et
groupe n-propyle, groupe iso-propyle, groupe n-butyle, groupe isobutyle, groupe sec-butyle, groupe tert-butyle, groupe n-pentyle, groupe isopentyle, groupe sec- pentyle, groupe tert-pentyle, groupe phényle, et groupe naphthyle, chacun étant substitué par au moins un élément choisi parmi deutérium, groupe alkyle C1-C10, groupe phényle ;
de préférence où
R1 à R7 sont chacun indépendamment choisis parmi hydrogène, deutérium, -F, groupe cyano, groupe nitro, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, groupes représentés par les Formules 9-1 à 9-22, groupes représentés par les Formules 10-1 à 10-144, et - Si(Q3)(Q4)(Q5) :
dans lequel, dans les Formules 9-1 à 9-22 et 10-1 à 10-144, i-Pr indique un groupe isopropyle, i-Bu indique un groupe isobutyle, t-Bu indique un groupe tert-butyle, TMS indique un groupe triméthylsilyle, Ph indique un groupe phényle, et * indique un site de liaison à un atome voisin.
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy1-1 à Cy1-39 :
dans lequel, dans les Formules Cy1-1 à Cy1-39,
X1 et R1 sont les mêmes que décrits dans la revendication 1,
X11 est O, S, N(Rn), ou C(R11)(R12),
X19 est C(R19) ou N,
R11 à R19 sont les mêmes que décrits en relation avec R1 dans la revendication 1,
a13 est un nombre entier de 0 à 3,
a14 est un nombre entier de 0 à 4, et
*, *', et *" indiquent chacun un site de liaison à un atome voisin ; et/ou
dans lequel
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy2-1 à Cy2-39 :
dans lequel, dans les Formules Cy2-1 à Cy2-39,
X2 et R2 sont les mêmes que décrits dans la revendication 1,
X21 est O, S, N(R21), ou C(R21)(R22),
X29 est C(R29) ou N,
R21 à R29 sont les mêmes que décrits en relation avec R2 dans la revendication 1,
a23 est un nombre entier de 0 à 3,
a24 est un nombre entier de 0 à 4, et
*, *', et *" indiquent chacun un site de liaison à un atome voisin ; et/ou
dans lequel
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy3-1 à Cy3-39 :
dans lequel, dans les Formules Cy3-1 à Cy3-39,
X3 et R3 sont les mêmes que décrits dans la revendication 1,
X31 est O, S, N(R31), ou C(R31)(R32),
X39 est C(R39) ou N,
R31 à R39 sont les mêmes que décrits en relation avec R3 dans la revendication 1,
a33 est un nombre entier de 0 à 3,
a34 est un nombre entier de 0 à 4, et
*, *', et *" indiquent chacun un site de liaison à un atome voisin ; et/ou
dans lequel
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cz-1 à Cz-27 :
dans lequel, dans les Formules Cz-1 to Cz-27,
R4 et R5 sont les mêmes que décrits dans la revendication 1,
a42 et a52 sont chacun indépendamment un nombre entier de 0 à 2,
a43 et a53 sont chacun indépendamment un nombre entier de 0 à 3,
a45 et a55 sont chacun indépendamment un nombre entier de 0 à 5, et
*, *', et *" indiquent chacun un site de liaison à un atome voisin.
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy1(1) à Cy1(26),
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy2(1) à Cy2(15),
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cy3(1) à Cy3(26), et
une partie représentée par
dans la Formule 1 est choisie parmi des groupes représentés par les Formules Cz(1) à Cz(21) :
dans lequel, dans les Formules Cy1(1) à Cy1(26), Cy2(1) à Cy2(15), Cy3(1) à Cy3(26), et Cz(1) à Cz(21),
X1 à X3 et R1 à R5 sont les mêmes que décrits dans la revendication 1,
X11 est O, S, N(R11), ou C(R11)(R12),
X21 et O, S, N(R21), ou C(R21)(R22),
X31 est O, S, N(R31), ou C(R31)(R32),
R1a à R1c, R11, et R12 sont les mêmes que décrits en relation avec R1 dans la revendication 1,
R2a à R2c, R21, et R22 sont les mêmes que décrits en relation avec R2 dans la revendication 1,
R3a à R3c, R31, et R32 sont les mêmes que décrits en relation avec R3 dans la revendication 1,
R1, R1a à R1c, R2, R2a à R2c, R3, R3a à R3c, R4, et R5 ne sont pas de l'hydrogène, et
*, *', et *" indiquent chacun un site de liaison à un atome voisin.
où, dans les formules 1-1 à 1-32,
M, X1 to X3, et R1 à R5 sont les mêmes que décrits dans la revendication 1,
X11 est O, S, N(R11), ou C(R11)(R12),
X21 est O, S, N(R21), ou C(R21)(R22),
X31 est O, S, N(R31), ou C(R31)(R32),
R1a, R1b, R11, et R12 sont les mêmes que décrits en relation avec R1 dans la revendication 1,
R2a, R2b, R21, et R22 sont les mêmes que décrits en relation avec R2 dans la revendication 1, et
R3a, R3b, R31, et R32 sont les mêmes que décrits en relation avec R3 dans la revendication 1.
une première électrode ;
une seconde électrode ; et
une couche organique disposée entre la première électrode et la seconde électrode,
où la couche organique comprend une couche d'émission, et
où la couche organique comprend au moins un composé organométallique de l'une quelconque des revendications 1 à 10.
la première électrode est une anode,
la seconde électrode est une cathode,
la couche organique comprend en outre une région de transport de trous disposée entre la première électrode et la couche d'émission et une région de transport d'électrons disposée entre la couche d'émission et la seconde électrode,
la région de transport de trous comprenant une couche d'injection de trous, une couche de transport de trous, et une couche de blocage d'électrons, ou toute combinaison de celles-ci, et
la région de transport d'électrons comprenant une couche de blocage de trous, une couche de transport d'électrons, et une couche d'injection d'électrons, ou toute combinaison de celles-ci.
la couche d'émission comprend en outre un hôte, et
une quantité de l'hôte est supérieure à une quantité du composé organométallique.
REFERENCES CITED IN THE DESCRIPTION
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Patent documents cited in the description