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

Abstract

An organometallic compound represented by Formula 1:

M.sub.1(L.sub.1).sub.n1(L.sub.2).sub.n2 Formula 1 wherein, in Formula 1, M.sub.1 is a transition metal, L.sub.1 is a ligand represented by Formula 1A, L.sub.2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2,

##STR00001## wherein X.sub.1 is C or N, X.sub.2 is C or N, X.sub.11 is C(R.sub.11) or N, X.sub.12 is C(R.sub.12) or N, X.sub.13 is C(R.sub.13) or N, X.sub.14 is C(R.sub.14) or N, X.sub.15 is C(R.sub.15) or N, X.sub.16 is C(R.sub.16) or N, and X.sub.17 is C(R.sub.17) or N, provided that at least one of X.sub.14 to X.sub.17 is not N; and at least one of R.sub.14 to R.sub.17 comprises Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); and the remaining substituent groups of Formulae 1A and 1B are as provided herein.

Claims

1. An organometallic compound represented by Formula 1:
M.sub.1(L.sub.1).sub.n1(L.sub.2).sub.n2 Formula 1 wherein, in Formula 1, M.sub.1 is a transition metal, L.sub.1 is a ligand represented by Formula 1A, L.sub.2 is a ligand represented by Formula 1B, n1 and n2 are each independently 1 or 2, ##STR00122## wherein, in Formulae 1A and 1B, X.sub.1 is C or N, and X.sub.2 is C or N, X.sub.11 is C(R.sub.11) or N, X.sub.12 is C(R.sub.12) or N, X.sub.13 is C(R.sub.13) or N, X.sub.14 is C(R.sub.14) or N, X.sub.15 is C(R.sub.15) or N, X.sub.16 is C(R.sub.16) or N, and X.sub.17 is C(R.sub.17) or N, provided that at least one of X.sub.14 to X.sub.17 is not N, ring CY.sub.2 is a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 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.1-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, Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), 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), at least one of R.sub.14 to R.sub.17 comprises Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), neighboring two or more of a plurality of R.sub.2 are optionally bonded 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.11 to R.sub.17 are optionally bonded 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, b2 is an integer from 1 to 10, * and * each indicate a binding site to M.sub.1, 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 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.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; 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; 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, 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 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 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.1-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1, wherein M.sub.1 is iridium, platinum, osmium, palladium, gold, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.

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

4. The organometallic compound of claim 1, wherein ring CY.sub.2 is 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 X.sub.11 is C(R.sub.11), X.sub.12 is C(R.sub.12), and X.sub.13 is C(R.sub.13).

6. The organometallic compound of claim 1, wherein i) X.sub.14 is C(R.sub.14), and X.sub.15 is C(R.sub.15), ii) X.sub.14 is C(R.sub.14), and X.sub.16 is C(R.sub.16), iii) X.sub.14 is C(R.sub.14), and X.sub.17 is C(R.sub.17), iv) X.sub.15 is C(R.sub.15), and X.sub.16 is C(R.sub.16), v) X.sub.15 is C(R.sub.15), and X.sub.17 is C(R.sub.17), or vi) X.sub.16 is C(R.sub.16), and X.sub.17 is C(R.sub.17).

7. The organometallic compound of claim 1, wherein at least one of R.sub.14 to R.sub.17 is: Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or a C.sub.6-C.sub.60 aryl group or a C.sub.1-C.sub.60 heteroaryl group, each substituted with Si(Q.sub.31)(Q.sub.32)(Q.sub.33) or Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), and Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 are each as described in claim 1.

8. The organometallic compound of claim 1, wherein Q.sub.1 to Q.sub.3 are each independently: 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; 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.

9. The organometallic compound of claim 1, wherein Li is a ligand represented by one of Formulae 1A-1 to 1A-6: ##STR00123## ##STR00124## wherein, in Formulae 1A-1 to 1A-6, X.sub.1, X.sub.2, X.sub.14 to X.sub.17, and R.sub.11 to R.sub.17 are each as described in claim 1, X.sub.21 is C(R.sub.21) or N, X.sub.22 is C(R.sub.22) or N, X.sub.23 is C(R.sub.23) or N, and X.sub.24 is C(R.sub.24) or N, R.sub.21 to R.sub.24 are each independently as described in connection with R.sub.2 in claim 1, at least one of R.sub.14 to R.sub.17 comprises Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), Q.sub.1 to Q.sub.3 are each as described in claim 1, and * and * each indicate a binding site to M.sub.1.

10. The organometallic compound of claim 1, wherein L.sub.1 is a ligand represented by Formula 1A(1)-1: ##STR00125## wherein, in Formula 1A(1)-1, X.sub.1, X.sub.2, ring CY.sub.2, R.sub.2, R.sub.11 to R.sub.17, and b2 are each as described in claim 1, at least one of R.sub.14 to R.sub.17 comprises Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), Q.sub.1 to Q.sub.3 are each as described in claim 1, and * and * each indicate a binding site to M.sub.1.

11. The organometallic compound of claim 1, wherein R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 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.20 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.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; 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 Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), 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.

12. The organometallic compound of claim 1, wherein R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 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 9-240, 10-1 to 10-129, or 10-201 to 10-353; or Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), or N(Q.sub.4)(Q.sub.5), and Q.sub.1 to Q.sub.5 are each as described in claim 1: ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##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## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## wherein, in Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

13. The organometallic compound of claim 1, wherein the organometallic compound is represented by Formula 5-1: ##STR00171## wherein, in Formula 5-1, M.sub.1, n1, n2, X.sub.1, X.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 are each as described in claim 1, at least one of R.sub.14 to R.sub.17 comprises Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), Q.sub.1 to Q.sub.3 are each as described in claims 1, and R.sub.21 to R.sub.24 are each independently as described in connection with R.sub.2 in claim 1.

14. The organometallic compound of claim 1, wherein the organometallic compound is represented by at least one of Compounds 1 to 54: ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185##

15. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer arranged 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 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 lease one organometallic compound in the emission layer, based on weight.

18. The organic light-emitting device of claim 16, wherein the emission layer emits light having a maximum emission wavelength of about 590 nanometers to about 650 nanometers.

19. The organometallic compound of claim 15, wherein the first electrode is an anode, the second electrode is a cathode, and the organic layer further comprises: a hole transport region arranged between the first electrode and the emission layer; and an electron transport region arranged between the emission layer and the second electrode, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and wherein 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

[0031] The above and other aspects, features, and advantages of certain exemplary embodiments will be more apparent from the following detailed description taken in conjunction with the FIGURE, which is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.

DETAILED DESCRIPTION

[0032] Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the detailed descriptions set forth herein. Accordingly, the exemplary embodiments are merely described below, by referring to the figure, to explain certain aspects. As used herein, the term and/or includes any and all combinations of one or more of the associated listed items. Expressions such as at least one of, when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] As used herein, an energy level (.e.g., a highest occupied molecular orbital (HOMO) energy level or a triplet (T.sub.1) energy level) is expressed as an absolute value from a vacuum level. In addition, when the energy level is referred to as being deep, high, or large, the energy level has a large absolute value based on 0 electron Volts (eV) of the vacuum level, and when the energy level is referred to as being shallow, low, or small, the energy level has a small absolute value based on 0 eV of the vacuum level.

[0040] An aspect provides an organometallic compound represented by Formula 1:

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

wherein M.sub.1 in Formula 1 is a transition metal.

[0041] In one or more embodiments, 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.

[0042] In one or more embodiments, M.sub.1 may be iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.

[0043] In one or more embodiments, M.sub.1 may be iridium, platinum, osmium, or rhodium.

[0044] In one or more embodiments, M.sub.1 may be iridium.

[0045] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0046] In one or more embodiments, a sum of n1 and n2 may be 2 or 3.

[0047] In one or more embodiments, M.sub.1 may be iridium, and the sum of n1 and n2 may be 3.

[0048] In one or more embodiments, M.sub.1 may be platinum, and the sum of n1 and n2 may be 2.

[0049] In Formula 1, L.sub.1 is a ligand represented by Formula 1A:

##STR00003##

wherein, in Formula 1A, X.sub.1 is C or N, and X.sub.2 is C or N.

[0050] In one or more embodiments, X.sub.1 may be N, and X.sub.2 may be C.

[0051] In Formula 1A, X.sub.11 is C(R.sub.11) or N, X.sub.12 is C(R.sub.12) or N, X.sub.13 is C(R.sub.13) or N, X.sub.14 is C(R.sub.14) or N, X.sub.15 is C(R.sub.15) or N, X.sub.16 is C(R.sub.16) or N, and X.sub.17 is C(R.sub.17) or N, provided that at least one of X.sub.14 to X.sub.17 is not N.

[0052] In one or more embodiments, X.sub.11 may be C(R.sub.11), X.sub.12 may be C(R.sub.12), and X.sub.13 may be C(R.sub.13).

[0053] In one or more embodiments, i) X.sub.14 may be C(R.sub.14), and X.sub.15 may be C(R.sub.15); ii) X.sub.14 may be C(R.sub.14), and X.sub.16 may be C(R.sub.16); iii) X.sub.14 may be C(R.sub.14), and X.sub.17 may be C(R.sub.17); iv) X.sub.15 may be C(R.sub.15), and X.sub.16 may be C(R.sub.16); v) X.sub.15 may be C(R.sub.15), and X.sub.17 may be C(R.sub.17); or vi) X.sub.16 may be C(R.sub.16), and X.sub.17 may be C(R.sub.17).

[0054] In Formula 1A, ring CY.sub.2 is a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.

[0055] In one or more embodiments, ring CY.sub.2 may 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 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.

[0056] For example, ring CY.sub.2 may be benzene group.

[0057] In one or more embodiments, a moiety represented by

##STR00004##

in Formula 1A may be a group represented by one of Formulae CY(2)-1 to CY(2)-16:

##STR00005## ##STR00006## ##STR00007##

wherein, in Formulae CY(2)-1 to CY(2)-16, [0058] R.sub.21 to R.sub.24 may each independently be as described in connection with R.sub.2, provide that R.sub.21 to R.sub.24 may not be hydrogen, [0059] ** indicates a binding site to M.sub.1, and [0060] * indicates a binding site to a neighboring atom.

[0061] In one or more embodiments, L.sub.1 may be a ligand represented by one of Formulae 1A-1 to 1A-6:

##STR00008## ##STR00009##

wherein, in Formulae 1A-1 to 1A-6, [0062] X.sub.1, X.sub.2, X.sub.14 to X.sub.17, and R.sub.11 to R.sub.17 may each be as described herein, [0063] X.sub.21 may be C(R.sub.21) or N, X.sub.22 may be C(R.sub.22) or N, X.sub.23 may be C(R.sub.23) or N, and X.sub.24 may be C(R.sub.24) or N, [0064] R.sub.21 to R.sub.24 may each independently be as described herein in connection with R.sub.2, [0065] at least one of R.sub.14 to R.sub.17 includes Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), and [0066] * and * each indicate a binding site to M.sub.1.

[0067] In one or more embodiments, L.sub.1 may be a ligand represented by Formula 1A(1)-1:

##STR00010##

wherein, in Formula 1A(1)-1, [0068] X.sub.1, X.sub.2, ring CY.sub.2, R.sub.2, R.sub.11 to R.sub.17, and b2 may each be as described herein, [0069] at least one of R.sub.14 to R.sub.17 includes Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), [0070] Q.sub.1 to Q.sub.3 may each be as described herein, and [0071] * and * each indicate a binding site to M.sub.1.

[0072] In one or more embodiments, in Formula 1A(1)-1, at least one of R.sub.14 to R.sub.17 may be: Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or a C.sub.6-C.sub.60 aryl group or a C.sub.1-C.sub.60 heteroaryl group, each substituted with Si(Q.sub.31)(Q.sub.32)(Q.sub.33) or Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), and [0073] Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 may each be as described herein.

[0074] In Formula 1, L.sub.2 is a ligand represented by Formula 1B:

##STR00011##

[0075] In Formulae 1A and 1B, R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 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.1-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, Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), 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).

[0076] In one or more embodiments, R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 may each independently be: [0077] 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; [0078] 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; [0079] 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; [0080] 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 [0081] Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), 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 [0082] Q.sub.1 to Q.sub.9 may each independently be: [0083] 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; [0084] 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 [0085] 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.

[0086] In one or more embodiments, R.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 may each independently be: [0087] 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; [0088] a group represented by one of Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-353; or [0089] Si(Q.sub.1)(Q.sub.2)(Q.sub.3), Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), or N(Q.sub.4)(Q.sub.5):

##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## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068##

wherein, in Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0090] In one or more embodiments, R.sub.33 may be hydrogen or deuterium.

[0091] In one or more embodiments, at least one of R.sub.14 to R.sub.17 may include Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0092] In one or more embodiments, at least one of R.sub.14 to R.sub.17 may include: [0093] Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or [0094] a C.sub.6-C.sub.60 aryl group or a C.sub.1-C.sub.60 heteroaryl group, each substituted with Si(Q.sub.31)(Q.sub.32)(Q.sub.33) or Ge(Q.sub.31)(Q.sub.32)(Q.sub.33).

[0095] In one or more embodiments, Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 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 Formula 1A, neighboring two or more of a plurality of R.sub.2 are optionally bonded 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.11 to R.sub.17 in Formula 1A are optionally bonded 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.

[0100] In Formula 1A, b2 is an integer from 1 to 10.

[0101] In Formulae 1A and 1B, * and * each indicate a binding site to M.sub.1.

[0102] In one or more embodiments, the organometallic compound may be represented by Formula 5-1:

##STR00069##

wherein, in Formula 5-1, [0103] M.sub.1, n1, n2, X.sub.1, X.sub.2, R.sub.11 to R.sub.17, and R.sub.31 to R.sub.33 may each be as described herein, [0104] at least one of R.sub.14 to R.sub.17 includes Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), [0105] Q.sub.1 to Q.sub.3 may each be as described herein, and [0106] R.sub.21 to R.sub.24 may each independently be as described in connection with R.sub.2.

[0107] In one or more embodiments, in Formula 5-1, at least one of R.sub.14 to R.sub.17 may be: [0108] Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or [0109] a C.sub.6-C.sub.60 aryl group or a C.sub.1-C.sub.60 heteroaryl group, each substituted with Si(Q.sub.31)(Q.sub.32)(Q.sub.33) or Ge(Q.sub.31)(Q.sub.32)(Q.sub.33).

[0110] In one or more embodiments, in Formula 5-1, [0111] i) R.sub.14 and R.sub.15 may each independently be hydrogen, deuterium, F, Cl, Br, I, SF.sub.5, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, or a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, and R.sub.17 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or [0112] ii) R.sub.16 may be: [0113] Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3); or [0114] a C.sub.6-C.sub.60 aryl group or a C.sub.1-C.sub.60 heteroaryl group, each substituted with Si(Q.sub.31)(Q.sub.32)(Q.sub.33) or Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), and [0115] R.sub.15 and R.sub.17 may each independently be hydrogen, deuterium, F, Cl, Br, I, SF.sub.5, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, or a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group.

[0116] In one or more embodiments, the organometallic compound may be represented by at least one of Compounds 1 to 54:

##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##

[0117] In one or more embodiments, the organometallic compound may be electrically neutral.

[0118] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1, and includes the ligands having structures represented by Formulae 1A and Formula 1B. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescence characteristics, and thus may have characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.

[0119] In addition, the organometallic compound represented by Formula 1 has excellent electrical mobility, and thus an electronic device, e.g., an organic light-emitting device, including at least one of the organometallic compounds represented by Formula 1 may have a low driving voltage, a high efficiency, and a long lifespan.

[0120] A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, singlet (S.sub.1) energy level, and triplet (T.sub.1) energy levels of some compounds of the organometallic compound represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimized at the B3LYP level, and results thereof are shown in Table 1. The energy levels are expressed in electron volts (eV).

TABLE-US-00001 TABLE 1 HOMO LUMO S.sub.1 T.sub.1 Compound (eV) (eV) (eV) (eV) 1 ?4.835 ?1.939 2.263 2.006 2 ?4.826 ?1.927 2.266 2.008 3 ?4.802 ?1.896 2.273 2.015

##STR00084##

[0121] From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as a dopant for an electronic device, e.g., an organic light-emitting device.

[0122] In one or more embodiments, a maximum emission wavelength (emission peak wavelength, ?.sub.max) in an emission spectrum or an electroluminescence (EL) spectrum of the organometallic compound may be about 590 nanometers (nm) to about 650 nm.

[0123] Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art and by referring to Synthesis Examples provided below.

[0124] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is arranged between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer further includes at least one of the organometallic compounds represented by Formula 1.

[0125] By including the organic layer including the aforementioned organometallic compound represented by Formula 1, the organic light-emitting device may have an excellent driving voltage, an excellent current efficiency, external quantum efficiency, an excellent roll-off ratio, and a relatively narrow full width at half maximum (FWHM) of an emission peak in the EL spectrum, and an excellent lifespan.

[0126] 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. Here, the organometallic compound represented by Formula 1 may serve as a dopant, and the emission layer may further include a host. When the emission layer further includes a host, an amount of the host in the emission layer may be greater than an amount of the at least one organometallic compound represented by Formula 1 in the emission layer, based on weight.

[0127] In one embodiment, the emission layer may emit a red light. In one or more embodiments, the emission layer may emit a blue light having a maximum emission wavelength of about 590 nm to about 650 nm.

[0128] The expression (an organic layer) includes at least one of organometallic compounds 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.

[0129] For example, the organic layer may include, as the at least one organometallic compound represented by Formula 1, 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 at least one organometallic compound represented by Formula 1, 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 all may exist in an emission layer).

[0130] 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.

[0131] 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 arranged between the first electrode and the emission layer; and an electron transport region arranged 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.

[0132] The term organic layer as used herein refers to a single layer and/or a plurality of layers arranged 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 a metal.

[0133] 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 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 the stated order.

[0134] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water repellency.

[0135] The first electrode 11 may be formed by, for example, depositing or sputtering, onto the substrate, a material for forming the first electrode 11. 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 for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (AlLi), calcium (Ca), magnesium-indium (MgIn), or magnesium-silver (MgAg).

[0136] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of 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.

[0137] The organic layer 15 may be arranged on the first electrode 11.

[0138] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0139] The hole transport region may be arranged between the first electrode 11 and the emission layer.

[0140] 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.

[0141] The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.

[0142] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like, or a combination thereof.

[0143] When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100? C. to about 500? C., a vacuum pressure of about 10.sup.?8 torr to about 10.sup.?3 torr, and a deposition rate of about 0.01 angstroms per second (?/sec) to about 100 ?/sec. However, the deposition conditions are not limited thereto.

[0144] When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 rpm to about 5,000 revolutions per minute (rpm), and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80? C. to about 200? C. However, the coating conditions are not limited thereto.

[0145] The 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.

[0146] 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(1-naphthyl)-N,N-diphenylbenzidine (NPB), ?-NPB, N,N-bis(3-methylphenyl)-N,N-diphenyl-[1,1-biphenyl]-4,4-diamine (TPD), 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, but embodiments are not limited thereto:

##STR00085## ##STR00086## ##STR00087##

wherein, in Formula 201, Ar.sub.101 and Ar.sub.102 may each independently be: [0147] 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 [0148] 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 chrysenylene group, a naphthacenyl 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 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, or a combination thereof.

[0149] In Formula 201, xa and xb may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0150] 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: [0151] 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 C.sub.1-C.sub.10 alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or the like), a C.sub.1-C.sub.10 alkoxy group (e.g., 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; [0152] 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.60 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 a combination thereof; [0153] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or [0154] 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 are not limited thereto.

[0155] In Formula 201, R.sub.109 may be: [0156] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or [0157] 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.

[0158] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:

##STR00088##

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

[0159] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of Compounds HT1 to HT20, but embodiments are not limited thereto:

##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096##

[0160] A thickness of the electron transport region 140 may be about 100 angstroms (?) to about 5,000 ?, for example, about 160 ? to about 4,000 ?. When the hole transport region 120 includes a hole injection layer, a hole transport layer, or a combination thereof, a thickness of the hole injection layer may be about 50 ? to about 9,000 ?, for example, about 100 ? to about 1,000 ?, and a thickness of the hole transport layer may be about 50 ? to about 2,000 ?, for example, about 100 ? to about 1,500 ?. 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.

[0161] 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.

[0162] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant are: a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ); a metal oxide, such as a tungsten oxide, or a molybdenum oxide; or a cyano group-containing compound, such as one or more of Compounds HT-D1 or F12, but embodiments are not limited thereto:

##STR00097##

[0163] The hole transport region may include a buffer layer.

[0164] 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.

[0165] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, although the deposition or coating conditions may vary according to a material that is used to form the emission layer.

[0166] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained herein.

[0167] The emission layer may include a host and a dopant, and the dopant may include at least one of the organometallic compounds represented by Formula 1.

[0168] The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (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-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50, or Compound H51, but embodiments are not limited thereto:

##STR00098## ##STR00099##

[0169] In one or more embodiments, the host may include a compound represented by Formula 301, but embodiments are not limited thereto:

##STR00100##

wherein, in Formula 301, Ar.sub.111 and Ar.sub.112 may each independently be: [0170] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or [0171] 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.

[0172] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be: [0173] a C.sub.1-C.sub.10 alkyl group unsubstituted or substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof; [0174] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group; [0175] 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 [0176] a group represented by:

##STR00101## [0177] but embodiments are not limited thereto.

[0178] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be: [0179] a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or [0180] 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.

[0181] In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.

[0182] In one or more embodiments, the host may include a compound represented by Formula 302, but embodiments are not limited thereto:

##STR00102##

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

[0183] In Formula 302, Ar.sub.126 and Ar.sub.127 may each independently be a C.sub.1-C.sub.10 alkyl group (e.g., a methyl group, an ethyl group, a propyl group, or the like).

[0184] 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.

[0185] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a structure in which a red emission layer, a green emission layer, and/or a blue emission layer is stacked, the emission layer may emit a white light.

[0186] When the emission layer includes a host and a dopant, an amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host in the emission layer, but embodiments are not limited thereto.

[0187] The thickness of the emission layer may be about 100 ? to about 1,000 ?, for example, about 200 ? to about 600 ?. When the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.

[0188] An electron transport region may be arranged on the emission layer.

[0189] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0190] 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 embodiments are not limited thereto. The electron transport layer may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0191] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer that constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer as described herein.

[0192] 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,O8)-(1,1-biphenyl-4-olato)aluminum (BAlq), but embodiments are not limited thereto:

##STR00103##

[0193] A thickness of the hole blocking layer may be about 20 ? to about 1,000 ?, for example, about 30 ? to about 300 ?. 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.

[0194] 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-hydroxy-quinolinato) aluminum (Alq.sub.3), bis(2-methyl-8-quinolinolato-N1,O8)-(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), but embodiments are not limited thereto:

##STR00104##

[0195] In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:

##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113##

[0196] A thickness of the electron transport layer may be about 100 ? to about 1,000 ?, for example, about 150 ? to about 500 ?. 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.

[0197] The electron transport layer may include a metal-containing material in addition to the material as described above.

[0198] 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, but embodiments are not limited thereto:

##STR00114##

[0199] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

[0200] The electron injection layer may include LiF, NaCl, CsF, Li.sub.2O, BaO, or a combination thereof.

[0201] A thickness of the electron injection layer may be about 1 ? to about 100 ?, for example, about 3 ? to about 90 ?. 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.

[0202] The second electrode 19 may be arranged on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, the material for forming the second electrode 19 may be Li, Mg, Al, Ag, AlLi, Ca, MgIn, MgAg, or the like. 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.

[0203] Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments are not limited thereto.

[0204] Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

[0205] The organometallic compound represented by Formula 1 may be able to provide high luminescence efficiency, and thus the diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have a high diagnostic efficiency.

[0206] The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, or the like, but embodiments are not limited thereto.

[0207] 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 non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, or 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.

[0208] 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 non-limiting examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, or the like.

[0209] 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).

[0210] 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 non-limiting examples thereof include an ethenyl group, a propenyl group, a butenyl group, or 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.

[0211] 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 non-limiting examples thereof include an ethynyl group, a propynyl group, or 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.

[0212] The term C.sub.3-C.sub.10 cycloalkyl group as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, or 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.

[0213] The term C.sub.1-C.sub.10 heterocycloalkyl group as used herein refers to a monovalent ring group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, or 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.

[0214] The term C.sub.3-C.sub.10 cycloalkenyl group as used herein refers to a monovalent ring group having 3 to 10 carbon atoms, at least one carbon-carbon double bond in the ring thereof, and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a norbornenyl group, or 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.

[0215] The term C.sub.1-C.sub.10 heterocycloalkenyl group as used herein refers to a ring group that has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom, 1 to 10 carbon atoms as ring-forming atoms, and at least one double bond in the ring structure thereof. Non-limiting examples of the C.sub.1-C.sub.10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or 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.

[0216] The term C.sub.6-C.sub.60 aryl group as used herein refers to a monovalent group having a carbocyclic aromatic ring 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 ring system having 6 to 60 carbon atoms. Non-limiting examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, or 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 rings may be fused to each other.

[0217] The term C.sub.7-C.sub.60 alkyl aryl group as used herein refers to a C.sub.6-C.sub.60 aryl group substituted with at least one C.sub.1-C.sub.60 alkyl group. The term C.sub.7-C.sub.60 aryl alkyl group as used herein refers to a C.sub.1-C.sub.60 alkyl group substituted with at least one C.sub.6-C.sub.60 aryl group.

[0218] The term C.sub.1-C.sub.60 heteroaryl group as used herein refers to a monovalent group having a carbocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms, and the term C.sub.1-C.sub.60 heteroarylene group as used herein refers to a divalent group having a carbocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms. Non-limiting 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, or the like. When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each include two or more rings, the rings may be fused to each other.

[0219] The term C.sub.2-C.sub.60 alkyl heteroaryl group as used herein refers to a C.sub.1-C.sub.60 heteroaryl group substituted with at least one C.sub.1-C.sub.60 alkyl group. The term C.sub.2-C.sub.60 heteroaryl alkyl group as used herein refers to a C.sub.1-C.sub.60 alkyl group substituted with at least one C.sub.1-C.sub.60 heteroaryl group.

[0220] 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).

[0221] The term C.sub.1-C.sub.60 heteroaryloxy group as used herein indicates OA.sub.104 (wherein A.sub.104 is the C.sub.1-C.sub.60 heteroaryl group), and the term C.sub.1-C.sub.60 heteroarylthio group as used herein indicates SA.sub.105 (wherein A.sub.105 is the C.sub.1-C.sub.60 heteroaryl group).

[0222] 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. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group or 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 above.

[0223] The term monovalent non-aromatic condensed heteropolycyclic group as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom selected from B, N, O, P, Si, S, Se, and Ge other than carbon atoms, as a ring-forming atom, and no aromaticity in the entire molecular structure thereof. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or 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 above.

[0224] 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.

[0225] 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 B, N, O, P, Si, S, Se, and Ge other than 1 to 30 carbon atoms as ring-forming atoms. The C.sub.1-C.sub.30 heterocyclic group may be a monocyclic group or a polycyclic group.

[0226] 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: [0227] 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; [0228] 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.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.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; [0229] 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; [0230] 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, 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 [0231] Si(Q.sub.31)(Q.sub.32)(Q.sub.33), Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), Si(Q.sub.33)(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 [0232] 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.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; or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0233] For example, 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 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, a C.sub.1-C.sub.60 alkyl group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.6-C.sub.60 aryl group, or a combination thereof.

[0234] Hereinafter, an organometallic compound represented by Formula 1 and an organic light-emitting device according to exemplary embodiments are described in further detail with reference to Synthesis Examples and Examples. However, embodiments 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

[0235] ##STR00115##

Synthesis of Compound 1A

[0236] Under nitrogen environment, 4-chloro-7-(trimethylsilyl)benzo[c][2,7]naphthyridine (1.00 grams (g), 3.48 millimoles (mmol)) and (3,5-dimethylphenyl)boronic acid (0.58 g, 3.87 mmol) were dissolved in 75 milliliters (mL) of 1,4-dioxane. After potassium carbonate (K.sub.2CO.sub.3) (1.11 g, 8.03 mmol) was dissolved in 35 mL deionized water (DI water), this mixed solution was added to the reaction mixture, and a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh.sub.3).sub.4) (0.20 g, 0.17 mmol) was added thereto. Afterwards, the resultant reaction mixture was stirred and heated under reflux at a temperature of 110? C. After cooling to room temperature, an extraction process was performed thereon, and solids thus obtained were purified by column chromatography (eluents: ethyl acetate (EA) and n-hexane), to obtain 1.13 g (yield of 91%) of Compound 1A, i.e., 4-(3,5-dimethylphenyl)-7-(trimethylsilyl)benzo[c][2,7]naphthyridine. The compound was identified by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.

[0237] HRMS (MALDI) calculated for C.sub.23H.sub.24N.sub.2Si: m/z: 356.54; found: 357.42.

Synthesis of Compound 1B

[0238] Compound 1A (1.06 g, 2.98 mmol) and iridium chloride trihydrate (0.50 g, 1.42 mmol) were dissolved in 21 mL of 2-ethoxyethanol and 7 mL of DI water, and the mixed solution was stirred and heated under reflux for 24 hours. Then, the reaction temperature was lowered to room temperature. Solids produced therefrom were separated by filtration and thoroughly washed with water/methanol/hexane in the stated order, and the resultant solid product was dried in a vacuum oven, to obtain 1.31 g (yield of 99%) of Compound 1B. The compound was used in the next reaction without further purification.

Synthesis of Compound 1

[0239] Pentane-2,4-dione (0.17 g, 1.7 mmol) and potassium carbonate (K.sub.2CO.sub.3) (0.24 g, 1.74 mmol) were added to Compound 1B (1.31 g, 0.70 mmol), and then mixed with 14 mL of 2-ethoxyethanol, followed by stirring at room temperature for 18 hours. After an extraction process was performed thereon, solids thus obtained were purified by column chromatography (eluents: methylene chloride (MC) and n-hexane), so as to obtain 1.13 g (yield of 81%) of Compound 1. The compound was identified by HRMS (MALDI) and HPLC analysis.

[0240] HRMS (MALDI) calculated for C.sub.51H.sub.53IrN.sub.4O.sub.2Si.sub.2: m/z: 1002.40; found: 1003.36.

Synthesis Example 2: Synthesis of Compound 2

[0241] ##STR00116##

Synthesis of Compound 2

[0242] 1.23 g (yield of 80%) of Compound 2 was obtained in a similar manner as in the Synthesis of Compound 1 of Synthesis Example 1, except that, in synthesizing Compound 1A, 4-chloro-7-(trimethylgermyl)benzo[c][2,7]naphthyridine (1.00 g, 3.02 mmol) was used instead of 4-chloro-7-(trimethylsilyl)benzo[c][2,7]naphthyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0243] HRMS (MALDI) calculated for C.sub.51H.sub.53Ge.sub.2IrN.sub.4O.sub.2: m/z: 1091.49; found: 1094.12.

Synthesis Example 3: Synthesis of Compound 3

[0244] ##STR00117##

Synthesis of Compound 3

[0245] 1.13 g (yield of 79%) of Compound 3 was obtained in a similar manner as in the Synthesis of Compound 1 of Synthesis Example 1, except that, in synthesizing Compound 1A, 4-chloro-8-methyl-7-(trimethylsilyl)benzo[c][2,7]naphthyridine (1.00 g, 3.32 mmol) was used instead of 4-chloro-7-(trimethylsilyl)benzo[c][2,7]naphthyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0246] HRMS (MALDI) calculated for C.sub.53H.sub.57IrN.sub.4O.sub.2Si.sub.2: m/z: 1030.45; found: 1031.38.

Synthesis Example 4: Synthesis of Compound 4

[0247] ##STR00118##

Synthesis of Compound 4

[0248] 1.12 g (yield of 71%) of Compound 4 was obtained in a similar manner as in the Synthesis of Compound 1 of Synthesis Example 1, except that, in synthesizing Compound 1A, 4-chloro-8-methyl-7-(trimethylgermyl)benzo[c][2,7]naphthyridine (1.00 g, 2.90 mmol) was used instead of 4-chloro-7-(trimethylsilyl)benzo[c][2,7]naphthyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0249] HRMS (MALDI) calculated for C.sub.53H.sub.57Ge.sub.2IrN.sub.4O.sub.2: m/z: 1119.54; found: 1120.48.

Example 1

[0250] 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.

[0251] Compound HT3 and F12-P-dopant were vacuum co-deposited in a weight ratio of 98:2 on the anode to form a hole injection layer having a thickness of 100 ?, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,600 ?.

[0252] Subsequently, Compound RH3 (host) and Compound 1 (dopant) were co-deposited in a weight ratio of 97:3 on the hole transport layer to form an emission layer having a thickness of 400 ?.

[0253] Then, Compound ETL and Liq-N-dopant were co-deposited in a volume ratio of 50:50 on the emission layer to form an electron transport layer having a thickness of 350 ?, Liq-N-dopant was vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ?, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 ?, thereby completing the manufacture of an organic light-emitting device.

##STR00119## ##STR00120##

Examples 2 to 4 and Comparative Example 1

[0254] Organic light-emitting devices were manufactured in a similar manner as in Example 1, except that compounds shown in Table 2 were each used instead of Compound 1 in forming an emission layer.

Evaluation Example 1: Characterization of Organic Light-Emitting Device

[0255] For the organic light-emitting devices of Examples 1 to 4 and Comparative Example 1, driving voltage (Volts, V), maximum external quantum efficiency (Max EQE, %), maximum luminescence wavelength (nm), full width at half maximum (FWHM, nm), and roll-off ratio (%) were evaluated, and the results are shown in Table 2. As evaluation apparatuses, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The roll-off ratio was calculated according to Equation 1:

[00001]$\begin{array}{cc}\mathrm{Roll}-\mathrm{off}\mathrm{ratio}=\left\{1-\left(\mathrm{efficiency}\left(\mathrm{at}3,500\mathrm{nit}\right)/\mathrm{maximum}\mathrm{luminescence}\mathrm{efficiency}\right)\right\}?100\%& \mathrm{Equation}1\end{array}$

TABLE-US-00002 TABLE 2 Maximum Dopant in Driving Max luminescence Roll-off emission voltage EQE wavelength FWHM ratio layer (V) (%) (nm) (nm) (%) Example 1 1 4.4 23 632 56 12 Example 2 2 4.5 23 630 56 12 Example 3 3 4.5 23 630 57 12 Example 4 4 4.5 23 629 57 12 Comparative CE1 4.7 20 633 62 15 Example 1

##STR00121##

[0256] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had characteristics of a low driving voltage, improved Max EQE, a narrow FWHM, and a low roll-off ratio.

[0257] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had a lower driving voltage, higher Max EQE, a narrower FWHM, and a lower roll-off ratio, compared to the organic light-emitting device of Comparative Example 1.

[0258] According to the one or more exemplary embodiments, an organometallic compound represented by Formula 1 has excellent electrical characteristics, and thus an electronic device, e.g., an organic light-emitting device, including at least one of the organometallic compound represented by Formula 1 may have a low driving voltage, high maximum external quantum efficiency, and a low roll-off ratio. Thus, due to the use of the organometallic compound represented by Formula 1, a high-quality organic light-emitting device may be embodied.

[0259] It should be understood that exemplary embodiments described herein should be considered in a descriptive sense only 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 other embodiments. While one or more exemplary embodiments have been described with reference to the figure, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.