IP Library › Granted Patent US 10,714,696
Granted Patent B2
US 10,714,696 · App. 15/092,120 · Granted Jul 14, 2020

Organometallic compound and organic light-emitting device including the same

Inventors: Kyuyoung Hwang (Anyang-si, KR); Ohyun Kwon (Yongin-si, KR); Yoonhyun Kwak (Seoul, KR); Kum Hee Lee (Suwon-si, KR); Hyeonho Choi (Seoul, KR); Whail Choi (Seoul, KR); Byoungki Choi (Hwaseong-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H01L51/0085C07F15/0033C09K11/025C09K11/06H05B33/14C09K2211/1029C09K2211/1044C09K2211/185H01L51/0059H01L51/0072H01L51/0081H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 10,714,696
App. No.
15/092,120
Granted
Jul 14, 2020
Kind
B2
Abstract

An organometallic compound represented by Formula 1: M(L 1 ) n1 (L 2 ) n2   Formula 1 wherein in Formula 1, M, L 1 , L 2 , n1, and n2 are the same as described in the specification.

Claims (158)

1. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2   Formula 1

M in Formula 1 is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh,

L 1 in Formula 1 is selected from a ligand represented by 2A-1 to 2A-5, 2A-11 to 2A-14, 2A-21 to 2A-25, 2A-31 to 2A-34, 2A-41 to 2A-45, 2A-51 to 2A-54, 2A-61 to 2A-65, 2A-71 to 2A-74, 2A-81 to 2A-85, 2A-91 to 2A-94, 2A-101 to 2A-105, 2A-111 to 2A-114, 2B-1 to 2B-3, 2B-11 to 2B-13, 2B-21 to 2B-23, 2B-31 to 2B-33, 2B-41 to 2B-43, 2B-51 to 2B-53, 2B-61 to 2B-63, 2B-71 to 2B-73, 2B-81 to 2B-83, and 2B-91 to 2B-93,

L 2 in Formula 1 is selected from ligands represented by Formula 2C,

each of * and * 1 in Formulae 2A-1 to 2A-5, 2A-11 to 2A-14, 2A-21 to 2A-25, 2A-31 to 2A-34, 2A-41 to 2A-45, 2A-51 to 2A-54, 2A-61 to 2A-65, 2A-71 to 2A-74, 2A-81 to 2A-85, 2A-91 to 2A-94, 2A-101 to 2A-105, 2A-111 to 2A-114, 2B-1 to 2B-3, 2B-11 to 2B-13, 2B-21 to 2B-23, 2B-31 to 2B-33, 2B-41 to 2B-43, 2B-51 to 2B-53, 2B-61 to 2B-63, 2B-71 to 2B-73, 2B-81 to 2B-83, 2B-91 to 2B-93, and 2C is a binding site to M in Formula 1,

n1 in Formula 1 is 1, 2, or 3, provided that when n1 is 2 or greater, two or more groups L 1 are the same or different,

n2 in Formula 1 is 0, 1, 2, 3, or 4, provided that when n2 is 2 or greater, two or more groups L 2 are the same or different,

in Formulae 2A-1 to 2A-5, 2A-11 to 2A-14, 2A-21 to 2A-25, 2A-31 to 2A-34, 2A-41 to 2A-45, 2A-51 to 2A-54, 2A-61 to 2A-65, 2A-71 to 2A-74, 2A-81 to 2A-85, 2A-91 to 2A-94, 2A-101 to 2A-105, 2A-111 to 2A-114, 2B-1 to 2B-3, 2B-11 to 2B-13, 2B-21 to 2B-23, 2B-31 to 2B-33, 2B-41 to 2B-43, 2B-51 to 2B-53, 2B-61 to 2B-63, 2B-71 to 2B-73, 2B-81 to 2B-83, and 2B-91 to 2B-93, X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), X 6 is N or C(R 6 ), and X 7 is N or C(R 7 ),

in Formula 2B-1 to 2B-3, 2B-11 to 2B-13, 2B-21 to 2B-23, 2B-31 to 2B-33, 2B-41 to 2B-43, 2B-51 to 2B-53, 2B-61 to 2B-63, 2B-71 to 2B-73, 2B-81 to 2B-83, and 2B-91 to 2B-93, Ti is selected from a single bond, *—O—*′, *—S—*′, *—N(R 31 )—*′, *—C(R 31 )(R 32 )—*′, *—C(R 31 )═C(R 32 )—*′, and *—Si(R 31 )(R 32 )—*′, wherein R 31 and R 32 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 30 carbocyclic group or a substituted or unsubstituted C 2 —C 30 heterocyclic group,

in Formulae 2A-1 to 2A-5, 2A-11 to 2A-14, 2A-21 to 2A-25, 2A-31 to 2A-34, 2A-41 to 2A-45, 2A-51 to 2A-54, 2A-61 to 2A-65, 2A-71 to 2A-74, 2A-81 to 2A-85, 2A-91 to 2A-94, 2A-101 to 2A-105, 2A-111 to 2A-114, 2B-1 to 2B-3, 2B-11 to 2B-13, 2B-21 to 2B-23, 2B-31 to 2B-33, 2B-41 to 2B-43, 2B-51 to 2B-53, 2B-61 to 2B-63, 2B-71 to 2B-73, 2B-81 to 2B-83, and 2B-91 to 2B-93, X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ), X 21 is O, S, N(R 21 ), or C(R 21 )(R 22 ),

in Formulae 2A-11, 2A-31, 2A-51, 2A-71, 2A-91 and 2A-111, at least one of X 11 to X 14 is N, in Formulae 2A-12 to 2A-14, 2A-32 to 2A-34, 2A-52 to 2A-54, 2A-72 to 2A-74, 2A-92 to 2A-94 and 2A-112 to 2A-114, at least one of X 11 to X 16 is N,

in Formulae 2B-11, 2B-31, 2B-51, 2B-71 and 2B-91, at least one of X 11 to X 13 is N,

in Formulae 2B-12, 2B-13, 2B-32, 2B-33, 2B-52, 2B-53, 2B-72, 2B-73, 2B-92 and 2B-, at least one of X 11 to X 15 is N,

R 1 to R 9 , R 10 to R 16 , R 21 , R 22 , R 31 , and R 32 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, —SF 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 1 —C 60 alkyl group, a substituted or unsubstituted C 2 —C 60 alkenyl group, a substituted or unsubstituted C 2 —C 60 alkynyl group, a substituted or unsubstituted C 1 —C 60 alkoxy group, a substituted or unsubstituted C 3 —C 10 cycloalkyl group, a substituted or unsubstituted C 1 —C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 —C 10 cycloalkenyl group, a substituted or unsubstituted C 1 —C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 —C 60 aryl group, a substituted or unsubstituted C 6 —C 60 aryloxy group, a substituted or unsubstituted C 6 —C 60 arylthio group, a substituted or unsubstituted C 1 —C 6 o heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(O 2 ), —Si(Q 3 )(O 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and —Ge(Q 51 )(Q 52 )(Q 53 ),

two or more of R 1 to R 3 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 30 carbocyclic group or a substituted or unsubstituted C 2 —C 30 heterocyclic group,

two or more of R 4 to R 7 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 30 carbocyclic group or a substituted or unsubstituted C 2 —C 30 heterocyclic group,

Y 4 and Y 5 in Formula 2C are each independently O, N, P, or As, and

at least one substituent of the substituted C 5 —C 30 carbocyclic group, substituted C 2 —C 30 heterocyclic group, substituted C 1 —C 60 alkyl group, substituted C 2 —C 60 alkenyl group, substituted C 2 —C 60 alkynyl group, substituted C 1 —C 60 alkoxy group, substituted C 3 —C 10 cycloalkyl group, substituted C 1 —C 10 heterocycloalkyl group, substituted C 3 —C 10 cycloalkenyl group, substituted C 1 —C 10 heterocycloalkenyl group, substituted C 6 —C 60 aryl group, substituted C 6 —C 60 aryloxy group, substituted C 6 —C 60 arylthio group, substituted C 1 —C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from

a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 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 1 —C 60 alkyl group, a C 2 —C 60 alkenyl group, a C 2 —C 60 alkynyl group, and a C 1 —C 60 alkoxy group;

a C 1 —C 60 alkyl group, a C 2 —C 60 alkenyl group, a C 2 —C 60 alkynyl group, and a C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 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 3 —C 10 cycloalkyl group, a C 1 —C 10 heterocycloalkyl group, a C 3 —C 10 cycloalkenyl group, a C 1 —C 10 heterocycloalkenyl group, a C 6 —C 60 aryl group, a C 6 —C 60 aryloxy group, a C 6 —C 60 arylthio group, a C 1 —C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), and —P(═O)(Q 18 )(Q 19 );

a C 3 —C 10 cycloalkyl group, a C 1 —C 10 heterocycloalkyl group, a C 3 —C 10 cycloalkenyl group, a C 1 —C 10 heterocycloalkenyl group, a C 6 —C 60 aryl group, a C 6 —C 60 aryloxy group, a C 6 —C 60 arylthio group, a C 1 —C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 —C 10 cycloalkyl group, a C 1 —C 10 heterocycloalkyl group, a C 3 —C 10 cycloalkenyl group, a C 1 —C 10 heterocycloalkenyl group, a C 6 —C 60 aryl group, a C 6 —C 60 aryloxy group, a C 6 —C 60 arylthio group, a C 1 —C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 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 1 —C 60 alkyl group, a C 2 —C 60 alkenyl group, a C 2 —C 60 alkynyl group, a C 1 —C 60 alkoxy group, a C 3 —C 10 cycloalkyl group, a C 1 —C 10 heterocycloalkyl group, a C 3 —C 10 cycloalkenyl group, a C 1 —C 10 heterocycloalkenyl group, a C 6 —C 60 aryl group, a C 6 —C 60 aryloxy group, a C 6 —C 60 arylthio group, a C 1 —C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), and —P(═O)(Q 28 )(Q 29 ); and

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), and —P(═O)(Q 38 )(Q 39 ),

wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , Q 31 to Q 39 , and Q 51 to Q 53 are each independently selected from a hydrogen, a deuterium, —F, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 —C 60 alkyl group, a C 2 —C 6 o alkenyl group, a C 2 —C 60 alkynyl group, a C 1 —C 60 alkoxy group, a C 3 —C 10 cycloalkyl group, a C 1 —C 10 heterocycloalkyl group, a C 3 —C 10 cycloalkenyl group, a C 1 —C 10 heterocycloalkenyl group, a C 6 —C 60 aryl group, a C 6 —C 60 aryl group substituted with one of a C 1 —C 60 alkyl group and a C 6 —C 60 aryl group, a C 6 —C 60 aryloxy group, a C 6 —C 60 arylthio group, a C 1 —C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein in Formula 1,

M is Ir or Os, n1+n2 is 3; or

M is Pt, n1+n2 is 2.

3. The organometallic compound of claim 1 , wherein Ti is selected from *—O—*′, *—C(R 31 )(R 32 )—*′, *—Si(R 31 )(R 32 )—′, and groups represented by Formulae 11-1 to 11-4,

wherein R 31 and R 32 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group:

4. The organometallic compound of claim 1 , wherein

R 1 to R 9 , R 10 to R 16 , R 21 , R 22 , R 31 , and R 32 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF 5 , a C 1 —C 20 alkyl group, and a C 1 —C 20 alkoxy group;

a C 1 —C 20 alkyl group and a C 1 —C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 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 1 —C 10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl 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 benzoimidazolyl 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, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl 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 benzoimidazolyl 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, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —CI, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 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 1 —C 20 alkyl group, a C 1 —C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl 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 benzoimidazolyl 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, and an imidazopyrimidinyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 4 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 );

wherein Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group.

5. The organometallic compound of claim 1 , wherein

R 1 to R 9 to R 16 , R 21 , R 22 , R 22 , R 10 , R 31 , and R 32 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 —C 10 alkyl group, a C 1 —C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 4 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

wherein Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group.

6. The organometallic compound of claim 1 , wherein

R 1 to R 9 , R 10 to R 16 , , R 2 , R 22 , R 31 , and R 32 are each independently selected from a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-36, —Si(Q 3 )(Q 4 )(Q 5 ), and -Ge(Q 51 )(Q 52 )(Q 53 ), and

Q 3 to Q 5 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group:

7. The organometallic compound of claim 1 , wherein

ligand L 1 in Formula 1 is selected from ligands represented by Formulae 2A-1 to 2A-5, 2A-21 to 2A-25, 2A-41 to 2A-45, 2A-61 to 2A-65, 2A-81 to 2A-85, 2A-101 to 2A-105, 2B-1 to 2B-3, 2B-21 to 2B-23, 2B-41 to 2B-43, 2B-61 to 2B-63, and 2B-81 to 2B-83:

8. The organometallic compound of claim 1 , wherein

T 1 is selected from *—O—*′, *—S—*′, *—C(R 3 )(R 32 )—*′, *—Si(R 3 )(R 32 )—*′, and groups represented by Formulae 11-1 to 11-4,

R 1 to R 9 , R 10 to R 16 , R 21 , R 22 R 31 , and R 32 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 —C 10 alkyl group, a C 1 —C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group, two neighboring substituents of R 1 to R 3 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 10 carbocyclic ring,

two neighboring substituents of R 4 to R 7 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 10 carbocyclic ring, and

two neighboring substituents of R 11 to R 16 are optionally linked to each other to form a substituted or unsubstituted C 5 —C 10 carbocyclic ring:

9. The organometallic compound of claim 1 , wherein

T 1 is selected from *—O—*′, *—S—*′, *—C(R 31 )(R 32 )—*′, *—Si(R 31 )(R 32 )—*′, and groups represented by Formulae 11-1 to 11-4,

R 1 to R 9 , R 10 to R 16 , R 21 , R 22 , R 31 , and R 32 are each independently selected from a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-36, —Si(Q 3 )(Q 4 )(Q 5 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

Q 3 to Q 5 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group:

10. An organometallic compound represented by Formula 1,

M(L 1 ) n1 (L 2 ) n2   Formula 1

wherein

ligand L 1 in Formula 1 is selected from ligands represented by Formulae 2A-1(1) to 2A-1(3), 2A-3(1) to 2A-3(3), 2A-11(1) to 2A-11(9), and 2B-11(1) to 2B-11(6):

M in Formula 1 is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh,

L 1 in Formula 1 is selected from a ligand represented by 2A-1(1) to 2A-1(3), 2A-3(1) to 2A-3(3), 2A-11(1) to 2A-11(9), and 2B-11(1) to 2B-11(6),

L 2 in Formula 1 is selected from ligands represented by Formula 2C,

each of * and *′ in Formulae 2A-1(1) to 2A-1(3), 2A-3(1) to 2A-3(3), 2A-11(1) to 2A-11(9), 2B-11(1) to 2B-11(6), and 2C is a binding site to M in Formula 1,

n1 in Formula 1 is 1, 2, or 3, provided that when n1 is 2 or greater, two or more groups L 1 are the same or different,

n2 in Formula 1 is 0, 1, 2, 3, or 4, provided that when n2 is 2 or greater, two or more groups L 2 are the same or different,

in Formulae 2A-1(1) to 2A-1(3), 2A-3(1) to 2A-3(3), 2A-11(1) to 2A-11(9), and 2B-11(1) to 2B-11(6),

X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 4 ), X 6 is N or C(R 6 ), X 7 is N or C(R 7 ),

T 1 is selected from *—O—*′, *—S—*′, *—C(R 31 )(R 32 )—*′, *—Si(R 31 )(R 32 )—*′, and groups represented by Formulae 11-1 to 11-4,

X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ),

X 21 is O, S, N(R 21 ), or C(R 21 )(R 22 ),

in Formulae 2A-11(1) to 2A-11(3), at least one of X 13 and X 14 is N,

in Formulae 2A-11(4) to 2A-11(6), at least one of X 11 and X 14 is N,

in Formulae 2A-11(7) to 2A-11(9), at least one of X 11 and X 12 is N,

in Formulae 2B-11(1) to 2B-11(3), X 13 is N,

in Formulae 2B-11(4) to 2B-11(6), X 11 is N,

R 1 to R 7 , R 11 to R 14 , , R 21 , R 22 , R 31 , R 32 , and R 41 to R 48 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 —C 10 alkyl group, a C 1 —C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group:

wherein selection of ligand L 1 is subject to limitations of claim 1 .

11. The organometallic compound of claim 1 , wherein

ligand L 2 in Formula 1 is selected from ligands represented by Formulae 3A to 3C:

in Formulae 3A to 3C,

Y 11 is O, N, N(Z 1 ), P(Z 1 )(Z 2 ), or As(Z 1 )(Z 2 ),

Y 12 is O, N, N(Z 3 ), P(Z 3 )(Z 4 ), or As(Z 3 )(Z 4 ),

CY 11 is a C 2 —C 30 heterocyclic group,

T 11 is selected from a single bond, a double bond, *—C(Z 11 )(Z 12 )—*′, *—C(Z 11 )═C(Z 12 )—*′, *—C(Z 11 )—*′, *—C(Z 11 )=*′, *=C(Z 11 )—C(Z 12 )═C(Z 13 )—*′, *—C(Z 11 )═C(Z 12 )—C(Z 13 )=*′, *—N(Z 11 )—*′, and a substituted or unsubstituted C 8 —C 30 arylene group,

a11 is an integer selected from 1 to 10,

Z 1 to Z 4 and Z 11 to Z 13 are each independently selected from a hydrogen, a deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 —C 60 alkyl group, a substituted or unsubstituted C 2 —C 60 alkenyl group, a substituted or unsubstituted C 2 —C 60 alkynyl group, a substituted or unsubstituted C 1 —C 60 alkoxy group, a substituted or unsubstituted C 3 —C 10 cycloalkyl group, a substituted or unsubstituted C 1 —C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 —C 10 cycloalkenyl group, a substituted or unsubstituted C 1 —C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 —C 60 aryl group, a substituted or unsubstituted C 6 —C 60 aryloxy group, a substituted or unsubstituted C 6 —C 60 arylthio group, a substituted or unsubstituted C 1 —C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),

d1 is an integer selected from 0 to 10, and

each of * and *′ is a binding site to M in Formula 1.

12. The organometallic compound of claim 11 , wherein

CY 11 is selected from a pyridine, a pyrimidine, a triazine, a pyrrole, a pyrazole, an imidazole, and a triazole,

Z 1 to Z 4 and Z 11 to Z 13 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 —C 10 alkyl group, a C 1 —C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group.

13. The organometallic compound of claim 1 , wherein

ligand L 2 in Formula 1 is selected from ligands represented by Formulae 3-1 to 3-14:

in Formulae 3-1 to 3-14,

X 31 is N or C(Z 1a ), X 32 is N or C(Z 1b ),

X 41 is O, S, N(Z 1a ), or C(Z 1a )(Z 1b ),

Z 1 to Z 4 , Z 1 , Z 1b , and Z 11 to Z 14 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomrnanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 —C 10 alkyl group, a C 1 —C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomrnenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), and -Ge(Q 51 )(Q 52 )(Q 53 ),

Q 1 to Q 9 and Q 51 to Q 53 are each independently selected from

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from a deuterium, a C 1 —C 10 alkyl group, and a phenyl group,

e2 is 1 or 2,

e3 is an integer selected from 1 to 3, and

e4 is an integer selected from 1 to 4.

14. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and at least one organometallic compound of claim 1 .

15. The organic light-emitting device of claim 14 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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

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

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

16. The organic light-emitting device of claim 14 , wherein the emission layer comprises the organometallic compound.

17. The organic light-emitting device of claim 16 , wherein the emission layer further comprises a host.

18. An organometallic compound, wherein

the organometallic compound is one of Compounds 51 to 60:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2016
From: HWANG, KYUYOUNG; KWON, OHYUN; KWAK, YOONHYUN; LEE, KUM HEE; CHOI, HYEONHO; CHOI, WHAIL; CHOI, BYOUNGKI
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 038292/0038 →
Priority Claims (1)
KR 10-2015-0109569 · Aug 3, 2015 · national
Continuity (1)
Related Publication 20170040551A1 · Feb 9, 2017