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

Abstract

An organometallic compound represented by Formula 1:

M.sub.1(L.sub.1).sub.n1(L.sub.2).sub.n2Formula 1

wherein, 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.43 is C(R.sub.43), N, or C bonded to Y.sub.3; X.sub.44 is C(R.sub.44), N, or C bonded to Y.sub.2 or Y.sub.3; X.sub.45 is C(R.sub.45), N, or C bonded to Y.sub.2 or Y.sub.3; X.sub.46 is C(R.sub.46), N, or C bonded to Y.sub.2, wherein i) X.sub.43 is C bonded to Y.sub.3, and X.sub.44 is C bonded to Y.sub.2; ii) X.sub.44 is C bonded to Y.sub.3, and X.sub.45 is C bonded to Y.sub.2; or iii) X.sub.45 is C bonded to Y.sub.3, and X.sub.46 is C bonded to Y.sub.2, and the remaining substituents are as described herein.

Claims

1. An organometallic compound, represented by Formula 1:
M.sub.1(L.sub.1).sub.n1(L.sub.2).sub.n2Formula 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, ##STR00151## wherein, in Formulae 1A, 1B, and 2, X.sub.1 is C or N, X.sub.2 is C or N, X.sub.3 is C or N, X.sub.4 is C or N, ring CY.sub.1, ring CY.sub.2, and ring CY.sub.5 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, ring CY.sub.3 is (i) a 6-membered carbocyclic group, (ii) a 6-membered heterocyclic group, (iii) a 6-membered carbocyclic group to which a C.sub.5-C.sub.30 carbocyclic group is condensed, or a 6-membered carbocyclic group to which a C.sub.1-C.sub.30 heterocyclic group is condensed, or (iv) a 6-membered heterocyclic group to which a C.sub.5-C.sub.30 carbocyclic group is condensed, or a 6-membered heterocyclic group to which a C.sub.1-C.sub.30 heterocyclic group is condensed, Z.sub.1 and Z.sub.2 are each independently Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), a1 and a2 are each independently an integer from 0 to 10, a sum of a1 and a2 is 1 or greater, X.sub.41 is C(R.sub.41) or N, X.sub.42 is C(R.sub.42) or N, X.sub.43 is C(R.sub.43), N, or C bonded to Y.sub.3 in Formula 2; X.sub.44 is C(R.sub.44), N, or C bonded to Y.sub.2 or Y.sub.3 in Formula 2; X.sub.45 is C(R.sub.45), N, or C bonded to Y.sub.2 or Y.sub.3 in Formula 2; X.sub.46 is C(R.sub.46), N, or C bonded to Y.sub.2 in Formula 2, with the proviso that i) X.sub.43 is C bonded to Y.sub.3 in Formula 2, and X.sub.44 is C bonded to Y.sub.2 in Formula 2; ii) X.sub.44 is C bonded to Y.sub.3 in Formula 2, and X.sub.45 is C bonded to Y.sub.2 in Formula 2; or iii) X.sub.45 is C bonded to Y.sub.3 in Formula 2, and X.sub.46 is C bonded to Y.sub.2 in Formula 2, Y.sub.1 is O, S, Se, B(R.sub.61), N(R.sub.61), or C(R.sub.61)(R.sub.62), Y.sub.2 is a single bond, O, S, Se, B(R.sub.63), N(R.sub.63), C(R.sub.63)(R.sub.64), Si(R.sub.63)(R.sub.64), or Ge(R.sub.63)(R.sub.64), Y.sub.3 is a single bond, O, S, Se, B(R.sub.65), N(R.sub.65), C(R.sub.65)(R.sub.66), Si(R.sub.65)(R.sub.66), or Ge(R.sub.65)(R.sub.66), wherein at least one of Condition 1 or 2 is satisfied:
Y.sub.2 is Si(R.sub.63)(R.sub.64), or Ge(R.sub.63)(R.sub.64),Condition 1
Y.sub.3 is Si(R.sub.65)(R.sub.66) or Ge(R.sub.65)(R.sub.66),Condition 2 R.sub.1 to R.sub.3, R.sub.5, R.sub.41 to R.sub.46, and R.sub.61 to R.sub.66 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.1a cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.1a 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), neighboring two or more of R.sub.1 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.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, b1 to b3 and b5 are each independently an integer from 1 to 10, * and * each indicate a binding site to M.sub.1 in Formulae 1A and 1B, * and * each indicate a binding site to an adjacent atom in Formula 2, a 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.1 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.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.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 Ir, and a sum of n1 and n2 is 3.

4. The organometallic compound of claim 1, wherein ring CY.sub.1 and ring CY.sub.2 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound of claim 1, wherein ring CY.sub.3 and ring CY.sub.5 are each independently a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

6. The organometallic compound of claim 1, wherein a moiety represented by ##STR00152## in Formula 1A is a group represented by one of Formulae CY(1)-1 to CY(1)-32: ##STR00153## ##STR00154## ##STR00155## ##STR00156## wherein, in Formulae CY(1)-1 to CY(1)-32, R.sub.11 to R.sub.14 are each independently as described in connection with R.sub.1 in claim 1, provided that R.sub.11 to R.sub.14 are not hydrogen, Z.sub.1 is as described in claim 1, * indicates a binding site to M.sub.1, and * indicates a binding site to a neighboring atom.

7. The organometallic compound of claim 1, wherein a moiety represented by ##STR00157## in Formula 1A is a group represented by one of Formulae CY(2A)-1 to CY(2A)-16: ##STR00158## ##STR00159## wherein, in Formulae CY(2A)-1 to CY(2A)-16, R.sub.21 to R.sub.24 are each independently as described in connection with R.sub.2 in claim 1, provided that R.sub.21 to R.sub.24 are not hydrogen, * indicates a binding site to M.sub.1, and * indicates a binding site to a neighboring atom.

8. The organometallic compound of claim 1, wherein a moiety represented by ##STR00160## in Formula 1B is a group represented by one of Formulae CY(3)-1 to CY(3)-16: ##STR00161## ##STR00162## wherein, in Formulae CY(3)-1 to CY(3)-16, R.sub.31 to R.sub.34 are each independently as described in connection with R.sub.3 in claim 1, provided that R.sub.31 to R.sub.34 are not hydrogen, * indicates a binding site to M.sub.1, and * indicates a binding site to a neighboring atom.

9. The organometallic compound of claim 1, wherein one of Y.sub.2 or Y.sub.3 is a single bond.

10. The organometallic compound of claim 1, wherein L.sub.1 is a ligand represented by Formula 1A-1: ##STR00163## wherein, in Formula 1A-1, 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.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, X.sub.24 is C(R.sub.24) or N, R.sub.11 to R.sub.14 are each independently as described in connection with R.sub.1 in claim 1, 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.11 to R.sub.14 or R.sub.21 to R.sub.24 is Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), wherein 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 L.sub.2 is a ligand represented by one of Formulae 1B-1 to 1B-3: ##STR00164## wherein, in Formulae 1B-1 to 1B-3, ring CY.sub.3, ring CY.sub.5, X.sub.41 to X.sub.46, Y.sub.1 to Y.sub.3, R.sub.3, b3, R.sub.5, and b5 are each as described in claim 1, and * and * each indicate a binding site to M.sub.1.

12. The organometallic compound of claim 1, wherein L.sub.2 is a ligand represented by one of Formulae 1B(1)-1 to 1B(1)-6: ##STR00165## ##STR00166## wherein, in Formulae 1B(1)-1 to 1B(1)-6, ring CY.sub.3, X.sub.41 to X.sub.46, Y.sub.1 to Y.sub.3, R.sub.3, and b3 are each as described in claim 1, X.sub.51 is C(R.sub.51) or N, X.sub.52 is C(R.sub.52) or N, X.sub.53 is C(R.sub.53) or N, X.sub.54 is C(R.sub.54) or N, R.sub.51 to R.sub.54 are each independently as described in connection with R.sub.5 in claim 1, and * and * each indicate a binding site to M.sub.1.

13. The organometallic compound of claim 1, wherein R.sub.1 to R.sub.3, R.sub.5, R.sub.41 to R.sub.46, and R.sub.61 to R.sub.66 are each independently: hydrogen, deuterium, F, Cl, Br, I, SF.sub.5, CDs, 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, CDs, 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.

14. The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Formulae 5-1 to 5-6: ##STR00167## ##STR00168## wherein, in Formulae 5-1 to 5-6, M.sub.1, n1, n2, X.sub.41 to X.sub.46, and Y.sub.1 to Y.sub.3 are each as described in claim 1, 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.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, X.sub.24 is C(R.sub.24) or N, X.sub.31 is C(R.sub.31) or N, X.sub.32 is C(R.sub.32) or N, X.sub.33 is C(R.sub.33) or N, X.sub.34 is C(R.sub.34) or N, X.sub.51 is C(R.sub.51) or N, X.sub.52 is C(R.sub.52) or N, X.sub.53 is C(R.sub.53) or N, X.sub.54 is C(R.sub.54) or N, R.sub.11 to R.sub.14 are each independently as described in connection with R.sub.1 in claim 1, 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.11 to R.sub.14 or R.sub.21 to R.sub.24 is Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), wherein Q.sub.1 to Q.sub.3 are each the same as described in claim 1, R.sub.31 to R.sub.34 are each independently as described in connection with R.sub.3 in claim 1, and R.sub.51 to R.sub.54 are each independently as described in connection with R.sub.5 in claim 1.

15. The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 128: ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202##

16. 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 of the organometallic compound of claim 1.

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

18. The organic light-emitting device of claim 16, wherein the emission layer emits a green light having a maximum emission wavelength of about 490 nanometers to about 550 nanometers.

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

20. An electronic apparatus, comprising the organic light-emitting device of claim 16.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0040] 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 accompanying drawing, in which:

[0041] The FIGURE is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.

DETAILED DESCRIPTION

[0042] Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing, 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 in further detail below, and by referring to the FIGURE, to explain certain aspects and features. 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] As used herein, when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (for example, phenyl, naphthyl, or the like) or as if it were the whole molecule (for example, benzene, naphthalene, or the like). It is to be understood that the nomenclature may be used interchangeably herein.

[0051] An aspect provides the organometallic compound represented by Formula 1:

M.sub.1(L.sub.1).sub.n1(L.sub.2).sub.n2Formula 1

wherein, In Formula 1, M.sub.1 is a transition metal.

[0052] For example, M.sub.1 may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements.

[0053] In one or more embodiments, M.sub.1 may be iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0054] In one or more embodiments, M.sub.1 may be iridium, platinum, osmium, or rhodium.

[0055] In one or more embodiments, M.sub.1 may be iridium.

[0056] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0057] In one or more embodiments, a sum of n1 and n2 may be 2 or 3.

[0058] In one or more embodiments, M.sub.1 may be iridium, and the sum of n1 and n2 may be 3.

[0059] In one or more embodiments, M.sub.1 may be platinum, and the sum of n1 and n2 may be 2.

[0060] L.sub.1 in Formula 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.

[0061] In one or more embodiments, X.sub.1 may be N, and X.sub.2 may be C.

[0062] In Formula 1A, ring CY.sub.1 and ring CY.sub.2 may each independently be a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.

[0063] In one or more embodiments, ring CY.sub.1 and ring CY.sub.2 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring system in which at least two first rings are condensed with each other, iv) a condensed ring system in which at least two second rings are condensed with each other, or v) a condensed ring system in which at least one first ring is condensed with at least one second ring, [0064] the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and [0065] the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0066] In one or more embodiments, ring CY.sub.1 and ring CY.sub.2 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a 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.

[0067] In one or more embodiments, [0068] ring CY.sub.1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and [0069] ring CY.sub.2 may be a benzene group or a naphthalene group.

[0070] In one or more embodiments, a moiety represented by

##STR00004##

in Formula 1A may be a group represented by one of Formulae CY(1)-1 to CY(1)-32:

##STR00005## ##STR00006## ##STR00007## ##STR00008##

wherein, in Formulae CY(1)-1 to CY(1)-32, [0071] R.sub.11 to R.sub.14 are each independently as described herein in connection with R.sub.1, provided that R.sub.11 to R.sub.14 are not hydrogen, [0072] Z.sub.1 is as described herein, [0073] * indicates a binding site to M.sub.1, and [0074] * indicates a binding site to a neighboring atom.

[0075] For example, R.sub.11 to R.sub.14 may each independently be a C.sub.1-C.sub.10 alkyl group substituted with at least one deuterium (for example, CD.sub.3, CD.sub.2H, CDH.sub.2, or the like).

[0076] In one or more embodiments, a moiety represented by

##STR00009##

in Formula 1A may be a group represented by one of Formulae CY(2)-1 to CY(2)-32:

##STR00010## ##STR00011## ##STR00012## ##STR00013##

wherein, in Formulae CY(2)-1 to CY(2)-32, [0077] R.sub.21 to R.sub.24 are each independently as described herein in connection with R.sub.2, provided that R.sub.21 to R.sub.24 are not hydrogen, [0078] Z.sub.2 is as described herein, [0079] * indicates a binding site to M.sub.1, and [0080] * indicates a binding site to a neighboring atom.

[0081] In one or more embodiments, a moiety represented by

##STR00014##

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

##STR00015## ##STR00016##

wherein, in Formulae CY(2A)-1 to CY(2A)-16, [0082] R.sub.21 to R.sub.24 are each independently as described herein in connection with R.sub.2, provided that R.sub.21 to R.sub.24 are not hydrogen, [0083] * indicates a binding site to M.sub.1, and [0084] * indicates a binding site to a neighboring atom.

[0085] In Formula 1A, Z.sub.1 and Z.sub.2 are each independently Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), wherein Q.sub.1 to Q.sub.3 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.1 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.

[0086] In one or more embodiments, Q.sub.1 to Q.sub.3 may each independently be: [0087] 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; [0088] 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 [0089] 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.

[0090] For example, Q.sub.1 to Q.sub.3 in Z.sub.1 may each independently be CH.sub.3, CD.sub.3, CD.sub.2H, or CDH.sub.2.

[0091] For example, Q.sub.1 to Q.sub.3 in Z.sub.2 may each independently be CH.sub.3, CD.sub.3, CD.sub.2H, or CDH.sub.2.

[0092] In Formula 1A, a1 and a2 are each independently an integer from 0 to 10, and [0093] a sum of a1 and a2 in Formula 1A is 1 or greater.

[0094] In one or more embodiments, the sum of a1 and a2 may be 1.

[0095] For example, i) a1 may be 1, and a2 may be 0, or ii) a1 may be 0, and a2 may be 1.

[0096] In one or more embodiments, L.sub.1 may be a ligand represented by Formula 1A-1:

##STR00017##

wherein, in Formula 1A-1, [0097] X.sub.1 may be C or N, and X.sub.2 may be C or N, [0098] X.sub.11 may be C(R.sub.11) or N, X.sub.12 may be C(R.sub.12) or N, X.sub.13 may be C(R.sub.13) or N, and X.sub.14 may be C(R.sub.14) or N, [0099] 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, [0100] R.sub.11 to R.sub.14 are each independently as described herein in connection with R.sub.1, [0101] R.sub.21 to R.sub.24 are each independently as described herein in connection with R.sub.2, [0102] at least one of R.sub.11 to R.sub.14 or R.sub.21 to R.sub.24 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), wherein Q.sub.1 to Q.sub.3 are each as described herein, and [0103] * and * each indicates a binding site to M.sub.1. [0104] L.sub.2 in Formula 1 is a ligand represented by Formula 1B:

##STR00018##

wherein, in Formula 1B, X.sub.3 is C or N, and X.sub.4 is C or N.

[0105] In one or more embodiments, X.sub.3 may be N, and X.sub.4 may be C.

[0106] In Formula 1B, ring CY.sub.3 is: (i) a 6-membered carbocyclic group; (ii) a 6-membered heterocyclic group; (iii) a 6-membered carbocyclic group to which a C.sub.5-C.sub.30 carbocyclic group is condensed, or a 6-membered carbocyclic group to which a C.sub.1-C.sub.30 heterocyclic group is condensed; or (iv) a 6-membered heterocyclic group to which a C.sub.5-C.sub.30 carbocyclic group is condensed, or a 6-membered heterocyclic group to which a C.sub.1-C.sub.30 heterocyclic group is condensed.

[0107] In one or more embodiments, ring CY.sub.3 may be i) a first ring, ii) a second ring, iii) a condensed ring group in which two or more first rings are condensed with each other, iv) a condensed ring group in which two or more second rings are condensed with each other, or v) a condensed ring group in which at least one first ring is condensed with at least one second ring, [0108] the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and [0109] the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0110] In one or more embodiments, ring CY.sub.3 may be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0111] In one or more embodiments, a moiety represented by

##STR00019##

in Formula 1B may be a group represented by one of Formulae CY(3)-1 to CY(3)-16:

##STR00020## ##STR00021##

wherein, in Formulae CY(3)-1 to CY(3)-16, [0112] R.sub.31 to R.sub.34 are each independently as described herein in connection with R.sub.3, provided that R.sub.31 to R.sub.34 are each not hydrogen, [0113] * indicates a binding site to M.sub.1, and [0114] * indicates a binding site to a neighboring atom.

[0115] In Formula 1B, X.sub.41 is C(R.sub.41) or N, and X.sub.42 is C(R.sub.42) or N.

[0116] In Formula 1B, X.sub.43 is C(R.sub.43), N, or C bonded to Y.sub.3 in Formula 2; X.sub.44 is C(R.sub.44), N, or C bonded to Y.sub.2 or Y.sub.3 in Formula 2; X.sub.45 is C(R.sub.45), N, or C bonded to Y.sub.2 or Y.sub.3 in Formula 2; X.sub.46 is C(R.sub.46), N, or C bonded to Y.sub.2 in Formula 2, [0117] with the proviso that i) X.sub.43 is C bonded to Y.sub.3 in Formula 2, and X.sub.44 is C bonded to Y.sub.2 in Formula 2; ii) X.sub.44 is C bonded to Y.sub.3 in Formula 2, and X.sub.45 is C bonded to Y.sub.2 in Formula 2; or iii) X.sub.45 is C bonded to Y.sub.3 in Formula 2, and X.sub.46 is C bonded to Y.sub.2 in Formula 2:

##STR00022##

[0118] The detailed description of Formula 2 is as described herein.

[0119] In Formula 1B, Y.sub.1 is O, S, Se, B(R.sub.61), N(R.sub.61), or C(R.sub.61)(R.sub.62).

[0120] In Formula 2, Y.sub.2 is a single bond, O, S, Se, B(R.sub.63), N(R.sub.63), C(R.sub.63)(R.sub.64), Si(R.sub.63)(R.sub.64), or Ge(R.sub.63)(R.sub.64).

[0121] In Formula 2, Y.sub.3 is a single bond, O, S, Se, B(R.sub.65), N(R.sub.65), C(R.sub.65)(R.sub.66), Si(R.sub.65)(R.sub.66), or Ge(R.sub.65)(R.sub.66).

[0122] In Formula 2, at least one of Condition 1 or 2 is satisfied:

Y.sub.2 is Si(R.sub.63)(R.sub.64) or Ge(R.sub.63)(R.sub.64),Condition 1

Y.sub.3 is Si(R.sub.65)(R.sub.66) or Ge(R.sub.65)(R.sub.66).Condition 2

[0123] In other words, in Formula 2, (a) Y.sub.2 is Si(R.sub.63)(R.sub.64) or Ge(R.sub.63)(R.sub.64); (b) Y.sub.3 is Si(R.sub.65)(R.sub.66) or Ge(R.sub.65)(R.sub.66); or (c) a combination thereof.

[0124] In one or more embodiments, one of Y.sub.2 or Y.sub.3 may be a single bond.

[0125] For example, Y.sub.2 may be a single bond, and Y.sub.3 may be Si(R.sub.65)(R.sub.66) or Ge(R.sub.65)(R.sub.66).

[0126] For example, Y.sub.2 may be Si(R.sub.63)(R.sub.64) or Ge(R.sub.63)(R.sub.64), and Y.sub.3 may be a single bond.

[0127] In Formula 2, ring CY.sub.5 is a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.

[0128] In one or more embodiments, ring CY.sub.5 may be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0129] In one or more embodiments, L.sub.2 may be a ligand represented by one of Formulae 1B-1 to 1B-3:

##STR00023##

wherein, in Formulae 1B-1 to 1B-3, [0130] ring CY.sub.3, ring CY.sub.5, X.sub.41 to X.sub.46, Y.sub.1 to Y.sub.3, R.sub.3, b3, R.sub.5, and b5 are each as described herein, and [0131] * and * each indicate a binding site to M.sub.1.

[0132] In one or more embodiments, L.sub.2 may be a ligand represented by one of Formulae 1B(1)-1 to 1B(1)-6:

##STR00024## ##STR00025##

wherein, in Formulae 1B(1)-1 to 1B(1)-6, [0133] ring CY.sub.3, X.sub.41 to X.sub.46, Y.sub.1 to Y.sub.3, R.sub.3, and b3 are each as described herein, X.sub.51 may be C(R.sub.51) or N, X.sub.52 may be C(R.sub.52) or N, X.sub.53 may be C(R.sub.53) or N, X.sub.54 may be C(R.sub.54) or N, [0134] R.sub.51 to R.sub.54 are each independently as described herein in connection with R.sub.5, and [0135] * and * each indicate a binding site to M.sub.1.

[0136] In Formulae 1A, 1B, and 2, R.sub.1 to R.sub.3, R.sub.5, R.sub.41 to R.sub.46, and R.sub.61 to R.sub.66 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).

[0137] In one or more embodiments, R.sub.1 to R.sub.3, R.sub.5, R.sub.41 to R.sub.46, and R.sub.61 to R.sub.66 may each independently be: [0138] 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; [0139] 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; [0140] 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; [0141] 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 [0142] 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 [0143] Q.sub.1 to Q.sub.9 may each independently be: [0144] 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; [0145] 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 [0146] 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.

[0147] In one or more embodiments, R.sub.1 to R.sub.3, R.sub.5, R.sub.41 to R.sub.46, and R.sub.61 to R.sub.66 may each independently be: [0148] 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; [0149] 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 10-350; or [0150] 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 [0151] Q.sub.1 to Q.sub.5 are as described herein.

##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##

[0152] 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 a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

[0153] In Formula 1A, neighboring two or more of R.sub.1 may optionally be 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.

[0154] In Formula 1A, neighboring two or more of R.sub.2 may optionally be 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.

[0155] In Formulae 1A, 1B, and 2, b1 to b3 and b5 are each independently an integer from 1 to 10.

[0156] In Formulae 1A, 1B, and 2, * and * each indicate a binding site to M.sub.1.

[0157] In one or more embodiments, the organometallic compound may be represented by one of Formulae 5-1 to 5-6:

##STR00065## ##STR00066##

wherein, in Formulae 5-1 to 5-6, [0158] M.sub.1, n1, n2, X.sub.41 to X.sub.46, and Y.sub.1 to Y.sub.3 are each as described herein, [0159] X.sub.11 may be C(R.sub.11) or N, X.sub.12 may be C(R.sub.12) or N, X.sub.13 may be C(R.sub.13) or N, and X.sub.14 may be C(R.sub.14) or N, [0160] 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, [0161] X.sub.31 may be C(R.sub.31) or N, X.sub.32 may be C(R.sub.32) or N, X.sub.33 may be C(R.sub.33) or N, and X.sub.34 may be C(R.sub.34) or N, [0162] X.sub.51 may be C(R.sub.51) or N, X.sub.52 may be C(R.sub.52) or N, X.sub.53 may be C(R.sub.53) or N, and X.sub.54 may be C(R.sub.54) or N, [0163] R.sub.11 to R.sub.14 are each independently as described herein in connection with R.sub.1, [0164] R.sub.21 to R.sub.24 are each independently as described herein in connection with R.sub.2, at least one of R.sub.11 to R.sub.14 or R.sub.21 to R.sub.24 is Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), wherein Q.sub.1 to Q.sub.3 are each as described herein, [0165] R.sub.31 to R.sub.34 are each independently as described herein in connection with R.sub.3, and [0166] R.sub.51 to R.sub.54 are each independently as described herein in connection with R.sub.5.

[0167] In one or more embodiments, in Formulae 5-1 to 5-6, at least one of R.sub.11 to R.sub.14 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0168] In one or more embodiments, in Formulae 5-1 to 5-6, at least one of R.sub.21 to R.sub.24 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0169] In one or more embodiments, the organometallic compound may be represented by one of Compounds 1 to 128:

##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087##

##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103##

[0170] In one or more embodiments, the organometallic compound may be electrically neutral.

[0171] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 described above, and includes a ligand having the structures represented by Formulae 1A and 1B. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescence characteristics, and has such characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.

[0172] In addition, the organometallic compound represented by Formula 1 has excellent electrical mobility, and thus, electronic devices including at least one of the organometallic compounds represented by Formula 1, for example, organic light-emitting devices including the organometallic compound represented by Formula 1 may have low driving voltage, high efficiency, and/or a long lifespan.

[0173] The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, singlet (S.sub.1) energy level, and triplet (T.sub.1) energy level of selected organometallic compounds 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 4.727 1.278 2.827 2.403 2 4.722 1.273 2.826 2.415 [00104][00105]

[0174] From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use as a dopant for an electronic device, for example, an organic light-emitting device.

[0175] In one or more embodiments, a maximum emission wavelength (maximum emission peak wavelength, .sub.max) of an emission peak of an emission spectrum or electroluminescence (EL) spectrum of the organometallic compound may be about 490 nm to about 550 nm. For example, the .sub.max may be about 500 nm to about 550 nm, about 490 nm to about 540 nm, about 500 nm to about 540 nm, about 510 nm to about 540 nm, or about 490 nm to about 530 nm.

[0176] 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.

[0177] 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 located 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.

[0178] The organic light-emitting device may have excellent driving voltage, high maximum external quantum efficiency, and/or high lifespan characteristics by having the organic layer including at least one of the organometallic compounds represented by Formula 1 as described above.

[0179] The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, at least one of the organometallic compounds represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may serve as a dopant, and the emission layer may further include a host. When the emission layer further includes a host, based on the weight, a content of the host may be greater than a content of the organometallic compound.

[0180] In one or more embodiments, the emission layer may emit a green light. For example, the emission layer may emit a green light having a maximum emission wavelength of about 490 nm to about 550 nm. For example, the maximum emission wavelength may be about 500 nm to about 550 nm, about 490 nm to about 540 nm, about 500 nm to about 540 nm, about 510 nm to about 540 nm, or about 490 nm to about 530 nm.

[0181] The expression (an organic layer) includes at least one of (the) organometallic compounds represented by Formula 1 and (an organic layer) includes at least one of the organometallic compound represented by Formula 1 as used herein may include a case in which (an organic layer) includes identical organometallic compounds represented by Formula 1 and a case in which (an organic layer) includes two or more different organometallic compounds represented by Formula 1.

[0182] 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 both may be located in an emission layer).

[0183] 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.

[0184] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, and 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.

[0185] The term organic layer as used herein refers to a single layer and/or a plurality of layers located between the first electrode and the second electrode of the organic light-emitting device. The organic layer may include, in addition to an organic compound, an organometallic complex including metal.

[0186] 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 further detail 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.

[0187] 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.

[0188] 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).

[0189] 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.

[0190] The organic layer 15 is located on the first electrode 11.

[0191] The organic layer 15 may include a hole transport region, an emission layer, an electron transport region, or a combination thereof.

[0192] The hole transport region may be located between the first electrode 11 and the emission layer.

[0193] 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.

[0194] 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.

[0195] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.

[0196] 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.

[0197] When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80 C. to about 200 C. However, the coating conditions are not limited thereto.

[0198] The conditions for forming the hole transport layer and the electron blocking layer may be similar to or the same as the conditions for forming the hole injection layer.

[0199] The hole transport region may include, for example, 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,Ndiphenylbenzidine (NPB), -NPB, N,N-bis(3-methylphenyl)-N,Ndiphenyl-[1,1-biphenyl]-4,4diamine (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:

##STR00106## ##STR00107## ##STR00108##

[0200] Ar.sub.101 and Ar.sub.102 in Formula 201 may each independently be: [0201] 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 [0202] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each substituted with at least one of deuterium, F, Cl, Br, I, SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a 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. [0203] xa and xb in Formula 201 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.

[0204] R.sub.101 to R.sub.108, R.sub.111 to R.sub.119 and R.sub.121 to R.sub.124 in Formulae 201 and 202 may each independently be: [0205] 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, pentyl group, or a hexyl group), a C.sub.1-C.sub.10 alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group), or a C.sub.1-C.sub.10 alkylthio group; [0206] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, or a C.sub.1-C.sub.10 alkylthio group, each substituted with at least one of deuterium, F, Cl, Br, I, SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof; [0207] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or [0208] 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.

[0209] R.sub.109 in Formula 201 may be: [0210] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or [0211] 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.1C.sub.20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.

[0212] According to one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A below, but embodiments are not limited thereto:

##STR00109##

[0213] R.sub.101, R.sub.111, R.sub.112, and R.sub.109 in Formula 201A are each as described herein.

[0214] For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include one or more of compounds HT1 to HT20 illustrated below, but embodiments are not limited thereto:

##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116##

[0215] A thickness of the hole transport region may be about 100 angstroms () to about 10,000 , for example, about 100 to about 1,000 . When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be about 50 to about 10,000 , 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 . Without wishing to be bound to theory, 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.

[0216] 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.

[0217] 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 include a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), or the like; a metal oxide, such as a tungsten oxide, a molybdenum oxide, or the like; or a cyano group-containing compound, such as one of Compounds HT-D1 or F12, but embodiments are not limited thereto:

##STR00117##

[0218] The hole transport region may include a buffer layer.

[0219] 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 the light-emitting device may be improved.

[0220] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.

[0221] 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.

[0222] 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.

[0223] 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(naphthalen-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(carbazol-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50, or Compound H51, but embodiments are not limited thereto:

##STR00118##

[0224] In one or more embodiments, the host may include a compound represented by Formula 301, but embodiments are not limited thereto:

##STR00119##

[0225] Ar.sub.111 and Ar.sub.112 in Formula 301 may each independently be: [0226] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or [0227] 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.

[0228] Ar.sub.113 to Ar.sub.116 in Formula 301 may each independently be: [0229] a C.sub.1-C.sub.10 alkyl group which is substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof; [0230] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group; [0231] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group, each substituted with 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 [0232] a group represented by the formula:

##STR00120## [0233] however, embodiments are not limited thereto.

[0234] Ar.sub.113 to Ar.sub.116 in Formula 301 may each independently be: [0235] a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or [0236] 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. [0237] g, h, i, and j in Formula 301 may each independently be an integer from 0 to 4, and g, h, i, and j may each independently be, for example, 0, 1, or 2.

[0238] In one or more embodiments, the host may include a compound represented by Formula 302, but embodiments are not limited thereto:

##STR00121##

[0239] Ar.sub.122 to Ar.sub.125 in Formula 302 are as described in detail in connection with Ar.sub.113 in Formula 301.

[0240] Ar.sub.126 and Ar.sub.127 in Formula 302 may each independently be a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

[0241] 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.

[0242] When the organic light-emitting device 10 is a full-color organic light-emitting device 10, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit a white light.

[0243] When the emission layer includes a host and a dopant, an amount of the dopant may be about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments are not limited thereto.

[0244] The thickness of the emission layer may be about 100 to about 1,000 , for example, about 200 to about 600 . Without wishing to be bound to theory, when the thickness of the emission layer 15 is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.

[0245] An electron transport region may be located on the emission layer.

[0246] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0247] 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, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

[0248] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0249] 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:

##STR00122##

[0250] A thickness of the hole blocking layer may be about 20 to about 1,000 , for example, about 30 to about 300 . Without wishing to be bound to theory, 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.

[0251] 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:

##STR00123##

[0252] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but embodiments are not limited thereto:

##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131##

[0253] A thickness of the electron transport layer may be about 100 to about 1,000 , for example, about 150 to about 500 . Without wishing to be bound to theory, 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.

[0254] The electron transport layer may include a metal-containing material in addition to the material as described above.

[0255] 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:

##STR00132##

[0256] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

[0257] The electron injection layer may include Compound ET-D1, LiF, NaCl, CsF, Li.sub.2O, BaO, or a combination thereof.

[0258] A thickness of the electron injection layer may be about 1 to about 100 , and, for example, about 3 to about 90 . Without wishing to be bound to theory, 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.

[0259] The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (AI), silver (Ag), aluminum-lithium (AlLi), calcium (Ca), magnesium-indium (MgIn), or magnesium-silver (MgAg) may be used as the material for forming the second electrode 19. 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.

[0260] Hereinbefore, the organic light-emitting device has been described with reference to FIGURE, but embodiments are not limited thereto.

[0261] Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

[0262] The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have a high diagnostic efficiency.

[0263] 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.

[0264] 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.

[0265] 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 isopropoxy group, or the like. 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).

[0266] 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.

[0267] 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.

[0268] The term C.sub.3-C.sub.10 cycloalkyl group as used herein refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl 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.

[0269] The term C.sub.1-C.sub.10 heterocycloalkyl group as used herein refers to a monovalent saturated 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 atom(s), 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.

[0270] The term C.sub.3-C.sub.10 cycloalkenyl group as used herein refers to a monovalent ring group that includes 3 to 10 carbon atoms as ring-forming atoms and at least one carbon-carbon double bond in the ring thereof, and has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl 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.

[0271] The term C.sub.1-C.sub.10 heterocycloalkenyl group as used herein refers to a monovalent 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 atom(s), and at least one double bond in its ring. 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.2-C.sub.10 heterocycloalkenylene group as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.10 heterocycloalkenyl group.

[0272] 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.

[0273] 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.

[0274] The term C.sub.1-C.sub.60 heteroaryl group as used herein refers to a monovalent group having a heterocyclic 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 atom(s). The term C.sub.1-C.sub.60 heteroarylene group as used herein refers to a divalent group having a heterocyclic 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 atom(s). 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.

[0275] 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.

[0276] 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).

[0277] The term C.sub.1-C.sub.60 heteroaryloxy group as used herein refers to 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 refers to SA.sub.105 (wherein A.sub.105 is the C.sub.1-C.sub.60 heteroaryl group).

[0278] 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.

[0279] 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 its entire molecular structure. 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.

[0280] The term C.sub.5-C.sub.30 carbocyclic group as used herein refers to a saturated or unsaturated ring 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.

[0281] The term C.sub.1-C.sub.30 heterocyclic group as used herein refers to a saturated or unsaturated ring group including 1 to 30 carbon atoms and at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring-forming atom(s). The C.sub.1-C.sub.30 heterocyclic group may be a monocyclic group or a polycyclic group.

[0282] 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: [0283] 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; [0284] 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; [0285] 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; [0286] 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, and 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.6 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 [0287] 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 [0288] 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.

[0289] 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: [0290] 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.1 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, [0291] 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.

[0292] Hereinafter, an organometallic compound represented by Formula 1 and an organic light-emitting device including the organometallic compound represented by Formula 1 according to exemplary embodiments are described in further detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording B was used instead of A used in describing Synthesis Examples means that 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 13

##STR00133##

Synthesis of Compound 13A

[0293] 2-phenyl-5-(trimethylgermyl)pyridine (3.0 grams (g), 11.03 millimoles (mmol)) and iridium chloride trihydrate (1.87 g, 5.3 mmol) were mixed with 90 milliliters (mL) of 2-ethoxyethanol and 30 mL of deionized (DI) water, and the mixed solution was stirred and heated under reflux for 24 hours. Then, the temperature of the product was lowered to room temperature. The resulting solid was separated by filtration, washed sufficiently with water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 3.1 g (yield of 76%) of Compound 13A.

Synthesis of Compound 13B

[0294] Compound 13A (3.1 g, 2.01 mmol) was mixed with 120 mL of dichloromethane (DCM), and then a mixture of silver trifluoromethanesulfonate (AgOTf) (1.09 g, 4.23 mmol) in 40 mL of methanol (MeOH) was added thereto. Afterwards, the resulting reaction mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil. The product was then filtered through Celite to remove a solid. The filtrate was then subjected to a reduced pressure to obtain a solid (Compound 13B) which was used in the next reaction without an additional purification process.

Synthesis of Compound 13

[0295] Compound 13B (2.8 g, 2.96 mmol) and 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]silolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine (1.28 g, 3.24 mmol) were mixed with 30 mL of 2-ethoxyethanol and 30 mL of dimethylformamide (DMF), and the mixed solution was stirred at 120 C. for 24 hours. Then, the temperature of the solution was lowered to room temperature. The solvent was removed under a reduced pressure, and the resultant solid was purified by column chromatography (eluents: hexane and ethyl acetate), to obtain 0.95 g of Compound 13 (yield of 28%). The obtained compound was identified by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.

[0296] HRMS (MALDI) calculated for C.sub.54H.sub.49D.sub.3Ge.sub.2IrN.sub.3OSi: m/z 1127.2121; found: 1127.2124.

Synthesis Example 2: Synthesis of Compound 19

##STR00134##

Synthesis of Compound 19

[0297] 0.84 g of Compound 19 was obtained (yield of 28%) in a similar manner as used to synthesize Compound 13 in Synthesis Example 1, except that 2-(11,11-dimethyl-11H-benzo[b]benzo[4,5]silolo[2,3-f]benzofuran-4-yl)-4-(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]silolo[3,2-g]benzofuran-10-yl)-4-(methyl-d.sub.3)pyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0298] HRMS (MALDI) calculated for C.sub.54H.sub.49D.sub.3Ge.sub.2IrN.sub.3OSi: m/z 1127.2121; found: 1127.2123.

Synthesis Example 3: Synthesis of Compound 25

##STR00135##

Synthesis of Compound 25

[0299] 0.75 g of Compound 25 was obtained (yield of 25%) in a similar manner as used to synthesize Compound 13 in Synthesis Example 1, except that Compound 25B was used instead of Compound 13B, and 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]silolo[3,2-g]benzofuran-10-yl)-4,5-bis(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]silolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0300] HRMS (MALDI) calculated for C.sub.55H.sub.48D.sub.6IrN.sub.3OSi.sub.3: m/z 1055.3581; found: 1055.3578.

Synthesis Example 4: Synthesis of Compound 31

##STR00136##

Synthesis of Compound 31

[0301] 0.68 g of Compound 31 was obtained (yield of 24%) in a similar manner as used to synthesize Compound 13 in Synthesis Example 1, except that Compound 31B was used instead of Compound 13B, and 2-(11,11-dimethyl-11H-benzo[b]benzo[4,5]silolo[2,3-f]benzofuran-4-yl)-4,5-bis(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]silolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

[0302] HRMS (MALDI) calculated for C.sub.55H.sub.48D.sub.6IrN.sub.3OSi.sub.3: m/z 1055.3581; found: 1055.3578.

Example 1

[0303] As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (mm)50 mm0.5 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.

[0304] Compounds HT3 and F12-P-Dopant were co-deposited by vacuum on the anode at a weight ratio of 98:2 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 1,650 .

[0305] Then, Compound GH3 (host) and Compound 13 (dopant) were co-deposited at a weight ratio of 92:8 on the hole transport layer to form an emission layer having a thickness of 400 .

[0306] Afterwards, Compound ET3 and Liq-N-Dopant were co-deposited on the emission layer at a volume ratio of 50:50 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.

##STR00137##

Examples 2 to 4 and Comparative Examples 1 to 5

[0307] 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 13 in forming an emission layer.

Evaluation Example 1: Characterization of Organic Light-Emitting Device

[0308] The driving voltage (Volts, V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (nm), and lifespan (LT.sub.97, %) of each of the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 to 9 were evaluated, and the results thereof are shown in Table 2. As evaluation apparatuses, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The lifespan (LT.sub.97, relative %) (at 6000 candela per square meter, cd/in.sup.2) was evaluated by using a measure of time taken for the initial luminance (100%) to decrease to 97%, and the lifespan values are shown as relative values to Comparative Example 1.

TABLE-US-00002 TABLE 2 Dopant Maximum compound Driving emission in voltage Max EQE wavelength Lifespan Emission layer (V) (%) (nm) (rel. %) Example 1 13 4.0 23 534 180 Example 2 19 4.0 23 538 200 Example 3 25 4.1 23 528 160 Example 4 31 4.1 23 530 170 Comparative CE1 4.2 22 524 100 Example 1 Comparative CE2 4.3 21 526 80 Example 2 Comparative CE3 4.1 22 526 100 Example 3 Comparative CE4 4.5 20 524 100 Example 4 Comparative CE5 4.2 22 528 110 Example 5 Comparative CE6 4.2 23 527 110 Example 6 Comparative CE7 4.2 23 530 120 Example 7 Comparative CE8 4.2 20 531 100 Example 8 Comparative CE9 4.2 20 534 130 Example 9 [00138][00139][00140][00141][00142][00143][00144][00145][00146][00147][00148][00149][00150]

[0309] From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 have a low driving voltage, an increased maximum external quantum efficiency, and a long lifespan.

[0310] It was also confirmed from Table 2 that the organic light-emitting devices of Examples 1 to 4 have a lower driving voltage, a higher maximum external quantum efficiency, and an improved lifespan, compared to the organic light-emitting devices of Comparative Examples 1 to 9.

[0311] As the organometallic compound represented by Formula 1 has excellent electrical characteristics, an electronic device employing at least one of the organometallic compounds represented by Formula 1, for example, an organic light-emitting device may have a low driving voltage, excellent external quantum efficiency, and/or a long lifespan. Thus, by using at least one of the organometallic compounds represented by Formula 1, a high-quality organic light-emitting device may be embodied.

[0312] It should be understood that exemplary embodiments described herein should be considered in a descriptive sense and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in 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.