ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE

Abstract

An organometallic compound, represented by Formula 1:

M.sub.1(Ln.sub.1).sub.n1(Ln.sub.2).sub.n2  Formula 1

wherein, in Formula 1, Ln.sub.1 is a ligand represented by Formula 1A, Ln.sub.2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2:

##STR00001##

wherein X.sub.1, X.sub.2, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, Y.sub.5, Y.sub.6, Y.sub.7, Y.sub.8, Y.sub.9, Y.sub.10, CY.sub.1, CY.sub.2, CY.sub.3, T.sub.1, T.sub.2, a1, a2, R.sub.10, R.sub.20, R.sub.30, b10, b20, and b30 are each as described herein.

Claims

1. An organometallic compound, represented by Formula 1:
M.sub.1(Ln.sub.1).sub.n1(Ln.sub.2).sub.n2  Formula 1 wherein, in Formula 1, M.sub.1 is a transition metal, Ln.sub.1 is a ligand represented by Formula 1A, Ln.sub.2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2, ##STR00139## wherein, in Formulae 1A and 1B, X.sub.1 is C or N, and X.sub.2 is C or N, Y.sub.1 is C(R.sub.41) or N, Y.sub.2 is C(R.sub.42) or N, Y.sub.3(R.sub.43) or N, Y.sub.4 is C(R.sub.44) or N, Y.sub.5 is C(R.sub.45) or N, Y.sub.6 is C(R.sub.46) or N, Y.sub.7 is C(R.sub.47) or N, Y.sub.8 is C(R.sub.48) or N, Y.sub.9 is C(R.sub.49) or N, and Y.sub.10 is C(R.sub.50) or N, CY.sub.1 and CY.sub.2 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, CY.sub.3 is a nitrogen-containing C.sub.1-C.sub.30 heterocyclic group, and T.sub.1 and T.sub.2 are each independently —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), a1 and a2 are each independently 0, 1, 2, 3, 4, or 5, the sum of a1 and a2 is an integer of 1 or greater, R.sub.10, R.sub.10a, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.2-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9), two or more of a plurality of R.sub.10(s) are optionally linked together to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of a plurality of R.sub.20(s) are optionally linked together to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of a plurality of R.sub.30(s) are optionally linked together to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, neighboring two or more of R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 are optionally linked together to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, b10, b20, and b30 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, at least one substituent of the substituted C.sub.5-C.sub.30 carbocyclic group, the substituted C.sub.1-C.sub.30 heterocyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.2-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.1-C.sub.60 heteroaryloxy group, the substituted C.sub.1-C.sub.60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is: deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.2-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —Ge(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), —P(═O)(Q.sub.18)(Q.sub.19), or a combination thereof; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.2-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.2-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.2-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —Ge(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), —P(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39), Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.2-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and * and *′ each indicate a binding site to M.sub.1.

2. The organometallic compound of claim 1, wherein M.sub.1 is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

3. The organometallic compound of claim 1, wherein M.sub.1 is Ir, and the sum of n1 and n2 is 3.

4. The organometallic compound of claim 1, wherein CY.sub.1 and CY.sub.2 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene 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 benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound of claim 1, wherein CY.sub.3 is a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

6. The organometallic compound of claim 1, wherein R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.10 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, a pyrimidinyl group, or a combination thereof; 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, or an imidazopyrimidinyl group; a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylthio 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, or a combination thereof; or —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9), and Q.sub.1 to Q.sub.9 are each independently: —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2; an n-propyl group, an isopropyl 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, or a naphthyl group; or an n-propyl group, an isopropyl 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, or a naphthyl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, or a combination thereof.

7. The organometallic compound of claim 1, wherein R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; or a group represented by one of Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350: ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## wherein, the Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201, 9,237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

8. The organometallic compound of claim 1, wherein CY.sub.1 is represented by one of Formulae 1-1 to 1-31: ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## wherein, in Formulae 1-1 to 1-31, T.sub.1 is the same as described in claim 1, a12 is 1 or 2, a13 is 1, 2, or 3, a14 is 1, 2, 3, or 4, R.sub.11 to R.sub.14 are each independently the same as described in connection with R.sub.10 in claim 1, but are each not hydrogen, * indicates a binding site to M.sub.1, and *′ indicates a binding site to a neighboring atom.

9. The organometallic compound of claim 1, wherein CY.sub.2 is represented by one of Formulae 2-1 to 2-31: ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## wherein, in Formulae 2-1 to 2-31, T.sub.2 is as described in claim 1, a22 is 1 or 2, a23 is 1, 2, or 3, a24 is 1, 2, 3, or 4, R.sub.21 to R.sub.24 are each independently as described in connection with R.sub.20 in claim 1, provided that R.sub.21 to R.sub.24 are each not hydrogen, * indicates a binding site to M.sub.1, and *″ indicates a binding site to a neighboring atom.

10. The organometallic compound of claim 1, wherein CY.sub.3 is represented by one of Formulae 3-1 to 3-16: ##STR00177## ##STR00178## wherein, in Formulae 3-1 to 3-16, R.sub.31 to R.sub.34 are each independently as described in connection with R.sub.30 in claim 1, but are each not hydrogen, and * indicates a binding site to M.sub.1, and *′ indicates a binding site to a neighboring atom.

11. The organometallic compound of claim 1, wherein the organometallic compound is a group represented by one of Formulae 11-1 to 11-8: ##STR00179## ##STR00180## ##STR00181## wherein, in Formulae 11-1 to 11-8, M.sub.1, n1, n2, and Y.sub.1 to Y.sub.10 are respectively as described in claim 1, X.sub.11 is C(T.sub.11), C(R.sub.11), or N, X.sub.12 is C(T.sub.12), C(R.sub.12), or N, X.sub.13 is C(T.sub.13), C(R.sub.13), or N, and X.sub.14 is C(T.sub.14), C(R.sub.14), or N, X.sub.21 is C(T.sub.21), C(R.sub.21), or N, X.sub.22 is C(T.sub.22), C(R.sub.22), or N, X.sub.23 is C(T.sub.23), C(R.sub.23), or N, and X.sub.24 is C(T.sub.24), C(R.sub.24), or N, X.sub.31 is C(R.sub.31) or N, X.sub.32 is C(R.sub.32) or N, X.sub.33 is C(R.sub.33) or N, and X.sub.34 is C(R.sub.34) or N, T.sub.11 to T.sub.14 are each independently as described in connection with T.sub.1 in claim 1, T.sub.21 to T.sub.24 are each independently as described in connection with T.sub.2 in claim 1, R.sub.11 to R.sub.14 are each independently as described in connection with R.sub.10 in claim 1, R.sub.21 to R.sub.24 are each independently as described in connection with R.sub.20 in claim 1, R.sub.31 to R.sub.34 are each independently as described in connection with R.sub.30 in claim 1, two or more of R.sub.11 to R.sub.14 are optionally linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.21 to R.sub.24 are optionally linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.31 to R.sub.34 are optionally linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a, and R.sub.10a is as described in connection with R.sub.10 in claim 1.

12. The organometallic compound of claim 1, wherein a1 is 1, and a2 is 0.

13. The organometallic compound of claim 1, wherein the ligand represented by Formula 1A includes one silyl group or one germyl group, and the ligand represented by Formula 1B does not include a silyl group or a germyl group.

14. The organometallic compound of claim 1, wherein the organometallic compound is one of Compounds 1 to 60: ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201##

15. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer further comprises at least one organometallic compound of claim 1.

16. The organic light-emitting device of claim 15, wherein the emission layer comprises the at least one organometallic compound.

17. The organic light-emitting device of claim 16, wherein the emission layer further comprises a host, and an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound in the emission layer.

18. The organic light-emitting device of claim 16, wherein the emission layer emits blue light having a maximum emission wavelength in a range of about 500 nanometers to about 600 nanometers.

19. The organic light-emitting device of claim 16, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer further comprises a hole transport region located between the first electrode and the emission layer, and an electron transport region located between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

20. An electronic apparatus, comprising the organic light-emitting device of claim 15.

Description

BRIEF DESCRIPTION OF THE DRAWING

[0037] The above and other aspects, features, and advantages of one or more exemplary embodiments will be more apparent from the following detailed description, taken in conjunction with the drawings, wherein:

[0038] The FIGURE is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.

DETAILED DESCRIPTION

[0039] Reference will now be made in further detail to one or more exemplary embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the one or more exemplary embodiments are merely described in further detail below, and by referring to the FIGURE to explain aspects where indicated. As used herein, the term “and/or” includes any and all combinations of one or more of the same 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.

[0040] The terminology used herein is for the purpose of describing one or more exemplary 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. 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] “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.

[0046] An aspect of the present disclosure provides an organometallic compound represented by Formula 1:

M.sub.1(Ln.sub.1).sub.n1(Ln.sub.2).sub.n2.  Formula 1

[0047] In Formula 1, M.sub.1 is a transition metal.

[0048] For example, M.sub.1 may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements.

[0049] In one or more embodiments, M.sub.1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0050] In one or more embodiments, M.sub.1 may be Ir, Pt, Os, or Rh.

[0051] In one or more embodiments, M.sub.1 may be Ir.

[0052] In Formula 1, n1 is 1 or 2, and n2 is 1, 2, or 3.

[0053] In one or more embodiments, the sum of n1 and n2 may be an integer of 2 or 3.

[0054] In one or more embodiments, M.sub.1 may be Ir, and the sum of n1 and n2 may be 3.

[0055] In one or more embodiments, M.sub.1 may be Pt, and the sum of n1 and n2 may be 2.

[0056] In Formula 1, Ln.sub.1 is a ligand represented by Formula 1A:

##STR00003##

wherein, in Formula 1A,

[0057] T.sub.1 and T.sub.2 are each independently —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3),

[0058] a1 and a2 are each independently 0, 1, 2, 3, 4, or 5,

[0059] the sum of a1 and a2 is an integer of 1 or greater, and

[0060] * and *′ each indicate a binding site to M.sub.1.

[0061] In one or more embodiments, T.sub.1 and T.sub.2 may each independently be —Si(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0062] In one or more embodiments, a1 and a2 may each independently be 0, 1, or 2.

[0063] In one or more embodiments, a1 and a2 may each independently be 0 or 1.

[0064] In one or more embodiments, a1 may be 1, and a2 may be 0.

[0065] In Formula 1A, X.sub.1 is C or N, and X.sub.2 is C or N.

[0066] In Formula 1A, CY.sub.1 and CY.sub.2 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.

[0067] In Formula 1, Ln.sub.2 is a ligand represented by Formula 11B:

##STR00004##

[0068] In Formula 1B, Y.sub.1 is C(R.sub.41) or N, Y.sub.2 is C(R.sub.42) or N, Y.sub.3 is C(R.sub.43) or N, Y.sub.4 is C(R.sub.44) or N, Y.sub.5 is C(R.sub.45) or N, Y.sub.5 is C(R.sub.46) or N, Y.sub.7 is C(R.sub.47) or N, Y.sub.8 is C(R.sub.48) or N, Y.sub.9 is C(R.sub.49) or N, and Y.sub.10 is C(R.sub.50) or N. * and *′ each indicate a binding site to M.sub.1.

[0069] In Formula 1B, CY.sub.3 is a nitrogen-containing C.sub.1-C.sub.30 heterocyclic group.

[0070] In one or more embodiments, CY.sub.1 may be i) a first ring, ii) a second ring, iii) a condensed cyclic group in which two or more first rings are condensed with each other, iv) a condensed cyclic group in which two or more second rings are condensed with each other, or v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring,

[0071] the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and

[0072] the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0073] In one or more embodiments, CY.sub.1 and CY.sub.2 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, 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 thiophene group, a furan group, an indole group, a benzoborole 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-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran 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-fluoren-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 pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole 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 benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0074] In one or more embodiments, CY.sub.1 and CY.sub.2 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0075] In one or more embodiments, CY.sub.1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

[0076] In one or more embodiments, CY.sub.2 may be a benzene group, a naphthalene 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 fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

[0077] In one or more embodiments, CY.sub.3 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

[0078] R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 in Formula 1 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.2-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), —Ge(Q.sub.3)(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9).

[0079] In Formula 1, b10, b20, and b30 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0080] In one or more embodiments, b10, b20, and b30 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8.

[0081] In one or more embodiments, b10, b20, and b30 may each independently be 1, 2, 3, or 4.

[0082] In one or more embodiments, b10, b20, and b30 may each independently be 1 or 2.

[0083] In one or more embodiments, b10, b20, and b30 may each independently be 1.

[0084] In one or more embodiments, R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 may each independently be:

[0085] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.20 alkylthio group;

[0086] a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.20 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.10 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, a pyrimidinyl group, or a combination thereof;

[0087] 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, or an imidazopyrimidinyl group;

[0088] 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, or an imidazopyrimidinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylthio 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, or a combination thereof;

[0089] —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9), or

[0090] A combination thereof.

[0091] In one or more embodiments, R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group; or

[0092] a group represented by one of Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350:

##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##

##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032##

##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048##

[0093] In Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

[0094] In one or more embodiments, R.sub.10, R.sub.20, R.sub.30, and R.sub.41 to R.sub.50 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a naphthyl group, or a group represented by one of Formulae 9-44 to 9-61.

[0095] In one or more embodiments, Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 may each independently be:

[0096] deuterium, —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2;

[0097] an n-propyl group, an isopropyl 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, or a naphthyl group; or

[0098] an n-propyl group, an isopropyl 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, or a naphthyl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, or a combination thereof.

[0099] In one or more embodiments, CY.sub.1 in Formula 1A may be represented by one of Formulae 1-1 to 1-31:

##STR00049## ##STR00050## ##STR00051## ##STR00052##

[0100] In Formulae 1-1 to 1-31,

[0101] T.sub.1 may be as described herein,

[0102] a12 may be 1 or 2,

[0103] a13 may be 1, 2, or 3,

[0104] a14 may be 1, 2, 3, or 4,

[0105] R.sub.11 to R.sub.14 may each independently be as described in connection with R.sub.10, but may each not be hydrogen, and

[0106] * indicates a binding site to M.sub.1, and

[0107] *′ indicates a binding site to a neighboring atom.

[0108] In one or more embodiments, CY.sub.2 in Formula 1A may be represented by one of Formulae 2-1 to 2-31:

##STR00053## ##STR00054## ##STR00055## ##STR00056##

[0109] In Formulae 2-1 to 2-31,

[0110] T.sub.2 may be as described herein,

[0111] a22 may be 1 or 2,

[0112] a23 may be 1, 2, or 3,

[0113] a24 may be 1, 2, 3, or 4,

[0114] R.sub.21 to R.sub.24 may each independently be as described in connection with R.sub.20, but may each not be hydrogen, and

[0115] * indicates a binding site to M.sub.1, and

[0116] *″ indicates a binding site to a neighboring atom.

[0117] In one or more embodiments, CY.sub.3 in Formula 1B may be represented by one of Formulae 3-1 to 3-16:

##STR00057## ##STR00058##

[0118] In Formulae 3-1 to 3-16,

[0119] R.sub.31 to R.sub.34 may each independently be as described in connection with R.sub.30, but may each not be hydrogen, and

[0120] indicates a binding site to M.sub.1, and

[0121] *′ indicates a binding site to a neighboring atom.

[0122] In one or more embodiments, the organometallic compound may be a compound represented by one of Formulae 11-1 to 11-8:

##STR00059## ##STR00060## ##STR00061##

[0123] In Formulae 11-1 to 11-8,

[0124] M.sub.1, n1, n2, and Y.sub.1 to Y.sub.10 may respectively be as described herein,

[0125] X.sub.11 may be C(T.sub.11), C(R.sub.11), or N, X.sub.12 may be C(T.sub.12), C(R.sub.12), or N, X.sub.13 may be C(T.sub.13), C(R.sub.13), or N, and X.sub.14 may be C(T.sub.14), C(R.sub.14), or N,

[0126] X.sub.21 may be C(T.sub.21), C(R.sub.21), or N, X.sub.22 may be C(T.sub.22), C(R.sub.22), or N, X.sub.23 may be C(T.sub.23), C(R.sub.23), or N, and X.sub.24 may be C(T.sub.24), C(R.sub.24), or N,

[0127] X.sub.31 may be C(R.sub.31) or N, X.sub.32 may be C(R.sub.32) or N, X.sub.33 may be C(R.sub.33) or N, and X.sub.34 may be C(R.sub.34) or N,

[0128] T.sub.11 to T.sub.14 may each independently be the same as described in connection with T.sub.1,

[0129] T.sub.21 to T.sub.24 may each independently be the same as described in connection with T.sub.2,

[0130] R.sub.11 to R.sub.14 may each independently be the same as described in connection with R.sub.10,

[0131] R.sub.21 to R.sub.24 may each independently be the same as described in connection with R.sub.20,

[0132] R.sub.31 to R.sub.34 may each independently be the same as described in connection with R.sub.30,

[0133] two or more of R.sub.11 to R.sub.14 may optionally be linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a,

[0134] two or more of R.sub.21 to R.sub.24 may optionally be linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a,

[0135] two or more of R.sub.31 to R.sub.34 may optionally be linked to each other to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a, and

[0136] R.sub.10a may be the same as described in connection with R.sub.10.

[0137] In one or more embodiments, examples of the “C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a” are a benzene group, a naphthalene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cycloheptane group, a bicyclo[2.2.1]heptane group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzosilole group, each unsubstituted or substituted with at least one R.sub.10a. R.sub.10a may be the same as described in connection with R.sub.10. The C.sub.5-C.sub.30 carbocyclic group and the C.sub.1-C.sub.30 heterocyclic group may respectively be the same as described herein.

[0138] In one or more embodiments, at least one of R.sub.10(s) in the number of b10, R.sub.20(s) in the number of b20, and R.sub.30(s) in the number of b30, and R.sub.41 to R.sub.50 may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl, an isopentyl, a 2-methylbutyl group, a sec-pentyl, a tert-pentyl, a neo-pentyl, a 3-pentyl, a 3-methyl-2-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.20 alkylphenyl group, a naphthyl group, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), each unsubstituted or substituted with deuterium.

[0139] In one or more embodiments, the ligand represented by Formula 1A in the organometallic compound may include 1 to 4 silyl groups or 1 to 4 germyl groups. In one or more embodiments, the ligand represented by Formula 1A may include 1 to 4 —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or 1 to 4 —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0140] In one or more embodiments, the ligand represented by Formula 1A may include 1 or 2 silyl groups or 1 or 2 germyl groups. In one or more embodiments, the ligand represented by Formula 1A may include 1 or 2 groups of the formula —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or 1 or 2 groups of the formula —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0141] In one or more embodiments, in Formula 1A, T.sub.1 may be —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), and a1 may be 1.

[0142] In one or more embodiments, the ligand represented by Formula 1A may include one silyl group or one germyl group, and the ligand represented by Formula 1B may not include a silyl group or a germyl group.

[0143] In one or more embodiments, the organometallic compound may be one of Compounds 1 to 60:

##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##

[0144] In one or more embodiments, the organometallic compound may be electrically neutral.

[0145] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1. That is, the ligand represented by Formula 1A is substituted with a silyl group or a germyl group, and the bidentate ligand represented by Formula 1B and including a triphenylene group is not substituted with a silyl group or a germyl group. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescence characteristics, and has such characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.

[0146] In addition, the organometallic compound represented by Formula 1 has excellent electrical mobility, and thus, electronic devices including the organometallic compound, for example, organic light-emitting devices including the organometallic compound may show low driving voltage, high efficiency, a long lifespan, and a reduced roll-off phenomenon.

[0147] In addition, the photochemically stability of the organometallic compound represented by Formula 1 is improved, and thus, electronic devices including the organometallic compound, for example, organic light-emitting devices including the organometallic compound may show high emission efficiency, long lifespan, and high color purity.

[0148] The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, energy gap, triplet (T.sub.1) energy level, single (Si) energy level, gap between S.sub.5 and T.sub.1, and S.sub.5 oscillation strength of the organometallic compound represented by Formula 1 were evaluated by density functional theory (DFT) using the Gaussian 09 program with the molecular structure optimization obtained at the B3LYP basis level, and results thereof are shown in Table 1 where energy is reported in electron Volts (eV).

TABLE-US-00001 TABLE 1 Compound HOMO LUMO S.sub.1 T.sub.1 structure (eV) (eV) (eV) (eV) Compound 1 −4.780 −1.338 2.778 2.489 Compound 2 −4.764 −1.321 2.777 2.487 Compound 19 −4.729 −1.296 2.763 2.482 Compound 20 −4.719 −1.288 2.755 2.478 [00089][00090][00091][00092]

[0149] Referring to Table 1, it was confirmed that the organometallic compound represented by Formula 1 has suitable electrical characteristics for use as a dopant in an electric device, for example, an organic light-emitting device.

[0150] In one or more embodiments, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be 70 nanometers (nm) or less. For example, the FWHM of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be from about 30 nm to about 65 nm, from about 40 nm to about 63 nm, or from about 45 nm to about 62 nm.

[0151] In one or more embodiments, the maximum emission wavelength (emission peak wavelength, λ.sub.max) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be from about 490 nm to about 550 nm.

[0152] Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples described herein.

[0153] Accordingly, the organometallic compound represented by Formula 1 may be suitable for use as a dopant in an organic layer, for example, an emission layer, of an organic light-emitting device. Thus, another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer that is located between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes at least one organometallic compound represented by Formula 1.

[0154] As described herein, due to the inclusion of the organic layer including the organometallic compound represented by Formula 1, the organic light-emitting device may have excellent characteristics in terms of driving Voltage, current efficiency, power efficiency, external quantum efficiency, lifespan, and/or color purity. Also, such an organic light-emitting device may have a reduced roll-off phenomenon and a relatively narrow electroluminescent (EL) spectrum emission peak FWHM.

[0155] The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the 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 in the emission layer is smaller than an amount of the host included in the emission layer).

[0156] In one or more embodiments, the emission layer may emit green light. For example, the emission layer may emit red light having a maximum emission wavelength in a range of about 490 nm to about 550 nm.

[0157] The expression “(an organic layer) includes at least one organometallic compound represented by Formula 1” as used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.

[0158] In one or more embodiments, the organic layer may include, as the organometallic compound, only Compound 1. In this embodiment, Compound 1 may be included in the 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 exist in an identical layer (for example, Compound 1 and Compound 2 may all exist in the emission layer).

[0159] 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.

[0160] In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0161] The term “organic layer” as used herein refers to a single layer and/or a plurality of layers located 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.

[0162] The FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments of the present disclosure 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 in this order.

[0163] A substrate may be additionally located under or below the first electrode 11 or above or on the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art 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/or water resistance.

[0164] The first electrode 11 may be, for example, formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, the material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), 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), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

[0165] The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.

[0166] The organic layer 15 may be located on the first electrode 11.

[0167] The organic layer 15 may include: the hole transport region; the emission layer; and the electron transport region.

[0168] The hole transport region may be located between the first electrode 11 and the emission layer.

[0169] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0170] The hole transport region may include only either a hole injection layer or a hole transport layer. 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, wherein constituting layers for each structure are sequentially stacked in this stated order from the first electrode 11.

[0171] 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 such as vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.

[0172] 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 in a range of about 100° C. to about 500° C., a vacuum pressure in a range of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition rate in a range of about 0.01 angstroms per second (A/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

[0173] When the hole injection layer is formed by spin coating, the coating conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating conditions may include a coating speed in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature for removing a solvent after coating in a range of about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0174] Conditions for forming the hole transport layer and the electron blocking layer may be the same as the conditions for forming the hole injection layer.

[0175] The hole transport region may include at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), pi-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TP, spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, or a compound represented by Formula 202:

##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097##

[0176] In Formula 201, Ar.sub.101 and Ar.sub.102 may each independently be: [0177] 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, or a pentacenylene group; or [0178] 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, or a pentacenylene group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

[0179] In Formula 201, xa and xb 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 xa and xb are not limited thereto.

[0180] In Formulae 201 and 202, R.sub.101 to R.sub.108, R.sub.111 to R.sub.119, and R.sub.121 to R.sub.124 may each independently be:

[0181] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, or the like), a C.sub.1-C.sub.10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like), or a C.sub.1-C.sub.10 alkylthio group;

[0182] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, or a C.sub.1-C.sub.10 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, 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, or combination thereof;

[0183] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or

[0184] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, 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 C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.1-C.sub.10 alkylthio group, or a combination thereof, but embodiments of the present disclosure are not limited thereto.

[0185] In Formula 201, R.sub.109 may be:

[0186] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or

[0187] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, 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 C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.

[0188] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

##STR00098##

wherein, in Formula 201A, R.sub.101, R.sub.111, R.sub.112, and R.sub.109 may each independently be as described herein.

[0189] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one of Compounds HT1 to HT20, but embodiments of the present disclosure are not limited thereto:

##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107##

[0190] A thickness of the hole transport region may be in a range of about 100 angstroms (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. 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.

[0191] 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.

[0192] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of 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 tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyano group-containing compound, such as Compound HT-D1 or F12, but are not limited thereto:

##STR00108##

[0193] The hole transport region may include a buffer layer.

[0194] 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.

[0195] Then, the emission layer may be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, and/or LB deposition. 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 material that is used to form the hole transport layer.

[0196] Meanwhile, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be selected from materials for the hole transport region described above and host materials to be explained later. However, the material for forming the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be mCP, which will be described below.

[0197] The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.

[0198] In one or more embodiments, the host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN, also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethylbiphenyl (CDBP), TCP, mCP, Compound H50, or Compound H51:

##STR00109##

[0199] In one or more embodiments, the host may further include a compound represented by Formula 301:

##STR00110##

wherein, in Formula 301, Ar.sub.111 and Ar.sub.112 may each independently be:

[0200] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or

[0201] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.

[0202] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be:

[0203] a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or

[0204] a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.

[0205] In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and for example, may each independently be 0, 1, or 2.

[0206] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be:

[0207] a C.sub.1-C.sub.10 alkyl group which is substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof;

[0208] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group;

[0209] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, or a combination thereof; or

##STR00111##

[0210] In one or more embodiments, the host may include a compound represented by Formula 302:

##STR00112##

wherein, in Formula 302, Ar.sub.122 to Ar.sub.125 may each independently be the same as described in connection with Ar.sub.113 in Formula 301.

[0211] In Formula 302, Ar.sub.126 and Ar.sub.127 may each independently be a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

[0212] In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may each independently be 0, 1, or 2.

[0213] When the organic light-emitting device 10 is a full-color organic light-emitting device 10, 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, based on 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, and various modifications are possible.

[0214] 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.

[0215] 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. When the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.

[0216] Next, the electron transport region is located on the emission layer.

[0217] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0218] 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.

[0219] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be the same as the conditions for forming the hole injection layer.

[0220] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-quinolinolato-N1,08)-(1,1′-biphenyl-4-olato)aluminum (BAlq), but embodiments of the present disclosure are not limited thereto:

##STR00113##

[0221] 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. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

[0222] The electron transport layer may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolinato)aluminum (Alq.sub.3), bis(2-methyl-8-quinolinolato-N1,08)-(1,1′-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ):

##STR00114##

[0223] In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments of the present disclosure are not limited thereto:

##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123##

[0224] 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. When the thickness of the electron transport layer is within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.

[0225] The electron transport layer may include a metal-containing material in addition to the material as described above.

[0226] The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate (LiQ)) or ET-D2:

##STR00124##

[0227] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

[0228] The electron injection layer may include LiF, NaCl, CsF, Li.sub.2O, BaO, or a combination thereof.

[0229] 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. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

[0230] The second electrode 19 is located 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 has a relatively low work function. For example, the material for forming the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (AI), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0231] Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.

[0232] Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

[0233] The organometallic compound represented by Formula 1 provides high luminescence efficiency, and accordingly, the diagnostic composition including the at least one organometallic compound may have high diagnostic efficiency.

[0234] The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

[0235] The term “C.sub.1-C.sub.60 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 are a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, and the like. The term “C.sub.1-C.sub.60 alkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.

[0236] The term “C.sub.1-C.sub.60 alkoxy group” as used herein refers to a monovalent group represented by —OA.sub.101(wherein A.sub.101 is the C.sub.1-C.sub.60 alkyl group), and examples thereof are a methoxy group, an ethoxy group, an isopropyloxy group, and the like.

[0237] The term “C.sub.1-C.sub.60 alkylthio group” as used herein refers to a monovalent group represented by —SA.sub.101′ (wherein A.sub.101′ is the C.sub.1-C.sub.60 alkyl group).

[0238] The term “C.sub.2-C.sub.60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof are an ethenyl group, a propenyl group, a butenyl group, and the like. The term “C.sub.2-C.sub.60 alkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkenyl group.

[0239] The term “C.sub.2-C.sub.60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof are an ethynyl group, a propynyl group, and the like. The term “C.sub.2-C.sub.60 alkynylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkynyl group.

[0240] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. The term “C.sub.3-C.sub.10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkyl group.

[0241] The term “C.sub.1-C.sub.10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof are a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. The term “C.sub.1-C.sub.10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkyl group.

[0242] The term “C.sub.3-C.sub.10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C.sub.3-C.sub.10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkenyl group.

[0243] The term “C.sub.2-C.sub.10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, Se, Ge, and S as a ring-forming atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C.sub.1-C.sub.10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. The term “C.sub.2-C.sub.10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.10 heterocycloalkenyl group.

[0244] The term “C.sub.6-C.sub.60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C.sub.6-C.sub.60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C.sub.6-C.sub.60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group each include two or more rings, the two or more rings may be fused to each other. The C.sub.7-C.sub.60 alkylaryl group refers to a C.sub.6-C.sub.60 aryl group substituted with at least one C.sub.1-C.sub.60 alkyl group.

[0245] The term “C.sub.1-C.sub.60 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, and 1 to 60 carbon atoms. The term “C.sub.1-C.sub.60 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, and 1 to 60 carbon atoms. Examples of the C.sub.1-C.sub.60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C.sub.6-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each include two or more rings, the two or more rings may be fused to each other. The C.sub.2-C.sub.60 alkylheteroaryl group refers to a C.sub.1-C.sub.60 heteroaryl group substituted with at least one C.sub.1-C.sub.60 alkyl group.

[0246] The term “C.sub.7-C.sub.60 alkyl aryl group” as used herein refers to a C.sub.5-C.sub.30 aryl group substituted with a C.sub.1-C.sub.30 alkyl group, and the term “C.sub.7-C.sub.60 aryl alkyl group” as used herein refers to a C.sub.1-C.sub.30 alkyl group substituted with a C.sub.6-C.sub.30 aryl group.

[0247] The term “C.sub.2-C.sub.60 alkyl heteroaryl group” as used herein refers to a C.sub.1-C.sub.30 heteroaryl group substituted with a C.sub.1-C.sub.30 alkyl group, and the term “C.sub.2-C.sub.60 heteroaryl alkyl group” as used herein refers to a C.sub.1-C.sub.30 alkyl group substituted with a C.sub.1-C.sub.30 heteroaryl group.

[0248] The term “C.sub.6-C.sub.60 aryloxy group” as used herein indicates —OA.sub.102 (wherein A.sub.102 is the C.sub.6-C.sub.60 aryl group), and the term “C.sub.6-C.sub.60 arylthio group” as used herein indicates —SA.sub.103 (wherein A.sub.103 is the C.sub.6-C.sub.60 aryl group).

[0249] The term “C.sub.1-C.sub.60 heteroaryloxy group” as used herein indicates —OA.sub.104 (wherein A.sub.104 is a C.sub.1-C.sub.60 heteroaryl group), and the term “C.sub.1-C.sub.60 heteroarylthio group” indicates —SA.sub.105 (wherein A.sub.105 is the C.sub.1-C.sub.60 heteroaryl group).

[0250] 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 no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are a fluorenyl group and the like. 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 described herein.

[0251] 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 with each other, a heteroatom selected from N, O, P, Si, Se, Ge, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are a carbazolyl group and the like. 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 described herein.

[0252] The term “C.sub.5-C.sub.30 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 C.sub.5-C.sub.30 carbocyclic group may be a monocyclic group or a polycyclic group.

[0253] The term “C.sub.1-C.sub.30 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, P, Si, Se, Ge, and S other than 1 to 30 carbon atoms. The C.sub.1-C.sub.30 heterocyclic group may be a monocyclic group or a polycyclic group.

[0254] As used herein, TMS represents * —Si(CH.sub.3).sub.3, and TMG represents * —Ge(CH.sub.3).sub.3.

[0255] At least one substituent of the substituted C.sub.5-C.sub.30 carbocyclic group, the substituted C.sub.1-C.sub.30 heterocyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.1-C.sub.60 heteroaryloxy group, the substituted C.sub.1-C.sub.60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0256] deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group;

[0257] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —Ge(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), —P(═O)(Q.sub.18)(Q.sub.19), or a combination thereof;

[0258] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0259] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —Ge(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), —P(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or

[0260] Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39), and

[0261] Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0262] Hereinafter, a compound and an organic light-emitting device according to exemplary embodiments are described in further detail with reference to Synthesis Examples and Examples. However, the compound and the organic light-emitting device of the present disclosure are not limited thereto. The wording “‘B’ was used instead of ‘A’” used in describing Synthesis Examples means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES

Synthesis Example 1: Synthesis of Compound 1

[0263] ##STR00125## ##STR00126## ##STR00127##

(1) Synthesis of Compound 1A (1)

[0264] 2-phenyl-5-(trimethylsilyl)pyridine (7.25 grams (g), 31.9 millimoles (mmol)) and iridium chloride (5.0 g, 14.2 mmol) were mixed with 150 milliliters (mL) of ethoxyethanol and 50 mL of deionize (DI) water, and the mixed solution was stirred under reflux for 24 hours. Then, the reaction temperature was allowed to lower to room temperature. The solid product thus obtained was separated by filtration, and the filtrate was washed with water, methanol, and hexane, in this stated order, and dried in a vacuum oven, to obtain 9.2 g (yield of 85%) of Compound 1A(1).

(2) Synthesis of Compound 1A

[0265] Compound 1A(1) (2.4 g, 1.6 mmol) and 75 mL of methylene chloride were mixed, and then, silver trifluoromethanesulfonate (AgOTf) (0.9 g, 3.4 mmol) was added thereto after being mixed with 25 mL of methanol. Afterwards, the reaction solution was stirred at room temperature for 18 hours while light was blocked with aluminum foil. The solid obtained by filtration through Celite was removed, and the filtrate was subjected to a reduced pressure to remove the solvent, so as to obtain a solid (Compound A) which was used in the next reaction without performing an additional purification process thereon.

(3) Synthesis of Compound 1B

[0266] In a nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxoborolane (2.7 g, 7.71 mmol) and 2-chloro-4-isopropylpyridine (1.0 g, 6.43 mmol) were dissolved in 75 mL of 1,4-dioxane. Then, a mixture containing potassium carbonate (K.sub.2CO.sub.3) (2.0 g, 19.27 mmol) dissolved in 25 mL of DI water was added to the reaction mixture, and a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh.sub.3).sub.4) (0.74 g, 0.64 mmol) was added thereto. Afterwards, the resultant reaction mixture was stirred under reflux at 100° C. After cooling to room temperature, an extraction process was performed thereon, and the solid thus obtained was subjected to column chromatography (eluent: ethyl acetate (EA) and n-hexane), so as to obtain 1.9 g (yield of 86%) of Compound 1B. The obtained compound was identified by high resolution mass spectrometry (HRMS) using matrix assisted laser desorption ionization (MALDI) and by high-performance liquid chromatography (HPLC) analysis.

[0267] HRMS (MALDI) calcd for C.sub.26H.sub.21N: m/z: 347.46 Found: 348.22.

(4) Synthesis of Compound 1

[0268] Compound 1B (1.2 g, 1.4 mmol) and 4-isopropyl-2-(triphenylen-2-yl)pyridine (0.5 g, 1.5 mmol) were mixed with 20 mL of 2-ethoxyethanol, and stirred under reflux for 24 hours. Then, the reaction temperature was reduced to room temperature. The resultant reaction mixture was subjected to reduced pressure to remove the solvent, and the solid thus obtained was subjected to column chromatography (eluent: methylene chloride (MC) and hexanes), so as to obtain 0.6 g (yield of 45%) of Compound 1. The obtained compound was identified by HRMS and HPLC analysis.

[0269] HRMS (MALDI) calcd for C.sub.54H.sub.54IrN.sub.3Si.sub.2: m/z: 991.42 Found: 992.33.

Synthesis Example 2: Synthesis of Compound 2

[0270] ##STR00128## ##STR00129## ##STR00130##

[0271] 0.52 g (yield of 38%) of Compound 2 was obtained in a similar manner as in the synthesis of Compound 1, except that 2-phenyl-5-(trimethylgermyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine. The obtained compound was identified by HRMS and HPLC analysis.

[0272] HRMS (MALDI) calcd for C.sub.54H.sub.52Ge.sub.2IrN.sub.3: m/z: 1080.51 Found: 1082.33.

Example 1

[0273] As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water, each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.

[0274] Compound HT3 and Compound F12 (p-dopant) were vacuum-co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.

[0275] Subsequently, Compound GH3 (host) and Compound 1 (dopant) were co-deposited at a weight ratio of 92:8 on the hole transport layer to form an emission layer having a thickness of 400 Å.

[0276] Then, Compound ET3 and LiQ (n-dopant) were co-deposited on the emission layer at the volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

##STR00131##

Example 2 and Comparative Examples 1 to 5

[0277] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds shown in Table 2 were respectively used instead of Compound 1 as a dopant in forming an emission layer.

[0278] The driving voltage (Volts, V), external quantum efficiency (Max EQE, %), maximum emission wavelength (λ.sub.max, nm) of each of the organic light-emitting devices of Examples 1 and 2 and Comparative Examples 1 to 5 were evaluated, and results thereof are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A) were used as apparatuses for evaluation.

TABLE-US-00002 TABLE 2 Driving Molecular voltage λ.sub.max Max EQE No. structure (V) (nm) (%) Example 1 Compound 1 4.1 528 22   Example 2 Compound 2 4.1 528 22   Comparative Example 1 Compound A 4.1 526 20   Comparative Example 2 Compound B 4.3 522 19.5 Comparative Example 3 Compound C 4.0 534 21   Comparative Example 4 Compound D 4.0 536 21   Comparative Example 5 Compound E 4.3 522 20.0 [00132][00133][00134][00135][00136][00137][00138]

[0279] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 and 2 had excellent EQE and low driving voltage. In addition, it was confirmed that the organic light-emitting devices of Examples 1 and 2 had lower or equivalent driving voltage and higher EQE than those of the organic light-emitting devices of Comparative Examples 1 to 5.

[0280] As described above, according to the one or more embodiments, an organometallic compound may have excellent electrical characteristics and thermal stability. In particular, the organometallic compound has a high glass transition temperature so that crystallization thereof may be prevented, and electric mobility thereof may be improved. Accordingly, an electronic device, such as an organic light-emitting device, using the organometallic compound may have low driving voltage, high efficiency, a long lifespan, a reduced roll-off ratio, and a relatively narrow FWHM of an emission peak in an electroluminescence spectrum.

[0281] Thus, due to the use of the organometallic compound, a high-quality organic light-emitting device may be implemented. In addition, an electronic apparatus including the organic light-emitting device may be provided.

[0282] It should be understood that the one or more exemplary embodiments described herein should be considered in a descriptive sense and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in one or more other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the figures, it will be understood by the person having ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.