IP Library Granted Patent US 12,152,042
Granted Patent B2
US 12,152,042 · App. 17/319,489 · Granted Nov 26, 2024

Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Inventors: Jongwon Choi (Yongin-si, KR); Yongsuk Cho (Hwaseong-si, KR); Seungyeon Kwak (Suwon-si, KR); Sangdong Kim (Seongnam-si, KR); Soyeon Kim (Seoul, KR); Sukekazu Aratani (Hwaseong-si, KR); Sunghun Lee (Hwaseong-si, KR); Jiyoun Lee (Anyang-si, KR); Dmitry Kravchuk (Hwaseong-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07F15/0033H10K85/342H10K50/15H10K50/16H10K50/171H10K50/18
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Quick Facts
Patent No.
US 12,152,042
App. No.
17/319,489
Granted
Nov 26, 2024
Kind
B2
Abstract

An organometallic compound represented by Formula 1: wherein, in Formula 1, R 37 is hydrogen, deuterium, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; and ring CY 1 , R 21 to R 26 , R 30a , and R 30b , are as described herein.

Claims (111)

1. An organometallic compound, represented by Formula 1:

wherein, in Formula 1,

ring CY 1 is a group represented by one of Formulae CY1(1) to CY1(15):

wherein,

X 1 to X 8 are each independently C or N, wherein at least one of X 1 to X 6 of Formulae CY1(1) to CY1(9) is C, and at least one of X 1 to X 8 of Formulae CY1(10) to CY1(15) is C,

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

a16 is an integer from 0 to 6,

a18 is an integer from 0 to 8,

in Formulae CY1(1) to CY1(15), * is a binding site to Ir in Formula 1, and *” is a binding site to a neighboring carbon atom in Formula 1,

R 30a is a group represented by *—C(R 31 )(R 32 )(R 33 ), 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

R 30b is a group represented by *—C(R 34 )(R 35 )(R 36 ), 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

R 0 , R 11 to R 19 , R 21 to R 26 , and R 31 to R 36 are each independently hydrogen, 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 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ), provided that each of R 31 to R 33 is not hydrogen, and provided that each of R 34 to R 36 is not hydrogen;

R 37 is hydrogen, deuterium, a substituted or unsubstituted C 1 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

two or more of a plurality of R 0 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of R 11 to R 19 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of R 11 to R 19 and R 0 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of R 21 to R 26 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of R 30a , R 30b , and R 37 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

R 10a is as described in connection with R 0 , and

a substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 1 -C 60 alkylthio group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 7 -C 60 alkyl aryl group, the substituted C 7 -C 60 aryl alkyl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 alkyl heteroaryl group, the substituted C 2 -C 60 heteroaryl alkyl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 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, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or 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, or a C 1 -C 60 alkoxy group, each substituted with 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 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or a combination 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with 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 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 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or a combination thereof;

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or a combination thereof,

wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 60 alkyl group which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 1 -C 60 alkylthio 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 which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof; a C 6 -C 60 aryloxy group; a C 6 -C 60 arylthio group; a C 1 -C 60 heteroaryl group; a C 1 -C 60 heteroaryl group which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof; a C 1 -C 60 heteroaryloxy group; a C 1 -C 60 heteroarylthio group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein

ring CY 11 in Formulae CY1-1 to CY1-3 is a condensed cyclic group wherein two or more first rings are condensed with each other, a condensed cyclic group wherein two or more second rings are condensed with each other, or a condensed cyclic group wherein at least one first ring is condensed with at least one second ring,

ring CY 12 in Formulae CY1-4 to CY1-9 is a first ring, a second ring, a condensed cyclic group wherein two or more first rings are condensed with each other, a condensed cyclic group wherein two or more second rings are condensed with each other, or a condensed cyclic group wherein at least one first ring is condensed with at least one second ring,

the first ring is a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a germole group, a borole group, a selenophene group, a phosphole group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, an azagermole group, an azaborole group, an azaselenophene group, or an azaphosphole group, and

the second ring is an adamantane group, a norbornane group, a norbornene group, a bicyclo [1.1.1] pentane group, a bicyclo [2.1.1] hexane group, a bicyclo [2.2.2] octane 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.

3. The organometallic compound of claim 1 , wherein R 0 , R 11 to R 19 , R 21 to R 26 , R 31 to R 33 , and R 30b are each independently:

hydrogen, deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C 1 -C 20 alkyl) dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C 1 -C 20 alkyl) dibenzothiophenyl group, or a combination thereof;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 1 -C 20 fluorinated alkyl group, a C 1 -C 20 alkoxy group, a deuterated C 1 -C 20 alkoxy group, a C 1 -C 20 fluorinated alkoxy group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C 1 -C 20 alkyl) dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C 1 -C 20 alkyl) dibenzothiophenyl group, or a combination thereof; or

—Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 );

wherein each of R 31 to R 33 is not hydrogen.

4. The organometallic compound of claim 1 , wherein at least one of R 21 to R 26 is not hydrogen.

5. The organometallic compound of claim 1 , wherein at least one of R 21 to R 26 is:

deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C 1 -C 20 alkyl) dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C 1 -C 20 alkyl) dibenzothiophenyl group, or a combination thereof;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 1 -C 20 fluorinated alkyl group, a C 1 -C 20 alkoxy group, a deuterated C 1 -C 20 alkoxy group, a C 1 -C 20 fluorinated alkoxy group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C 1 -C 20 alkyl) dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C 1 -C 20 alkyl) dibenzothiophenyl group, or a combination thereof; or

—Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ).

6. The organometallic compound of claim 1 , wherein

ring CY 1 is a group represented by one of Formulae CY1-1 to CY1-3, and

at least one R 0 in the number of a0 in Formulae CY1-1 to CY1-3 is each independently deuterium, —F, a substituted or unsubstituted C 1 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

7. The organometallic compound of claim 1 , wherein

ring CY 1 is a group represented by one of Formulae CY1-1 to CY1-3, and

at least one of R 23 to R 26 is not hydrogen.

8. The organometallic compound of claim 1 , wherein a group represented by

in Formula 1 is a group represented by one of Formulae CY2-1 to CY2-59:

wherein, in Formulae CY2-1 to CY2-59,

R 21 to R 26 are each independently a group as described in claim 1 , provided that each of R 21 to R 26 is not hydrogen,

is a binding site to Ir in Formula 1, and

″ is a binding site to a neighboring atom in Formula 1.

9. The organometallic compound of claim 1 , wherein a group represented by

in Formula 1 is a group represented by one of Formulae 4-1 to 4-3:

wherein, in Formulae 4-1 to 4-3,

R 21 to R 26 and R 10a are each independently a group as described in claim 1 ,

ring CY 21 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

a2 is an integer from 0 to 20,

is a binding site to Ir in Formula 1, and

″ is a binding site to a neighboring atom in Formula 1.

10. The organometallic compound of claim 1 , wherein

R 30b is a group represented by *—C(R 34 )(R 35 )(R 36 ),

R 34 to R 36 are each independently a group as described in claim 1 , and

each of R 34 to R 36 is not hydrogen or deuterium.

11. The organometallic compound of claim 1 , wherein

R 30a is a group represented by *—C(R 31 )(R 32 )(R 33 ),

R 31 to R 33 are each independently a group as described in claim 1 , and

at least one of R 31 to R 33 is not a methyl group.

12. The organometallic compound of claim 1 , wherein

at least one of Condition A1 to Condition A3 is satisfied, or

Condition A1 and Condition A2 are each satisfied,

Condition A1

R 30a is a group represented by *—C(R 31 )(R 32 )(R 33 ), and

R 31 to R 33 are each independently a substituted or unsubstituted C 1 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Condition A2

R 30a is a group represented by *—C(R 31 )(R 32 )(R 33 ),

R 31 to R 33 are each independently a group as defined in Condition A1, and

at least one of R 31 to R 33 is independently a substituted or unsubstituted C 2 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Condition A3

R 30a is 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

13. The organometallic compound of claim 1 , wherein

at least one of Condition B1 to Condition B3 is satisfied, or

Condition B1 and Condition B2 are each satisfied,

Condition B1

R 30b is a group represented by *—C(R 34 )(R 35 )(R 36 ), and

R 34 to R 36 are each independently a substituted or unsubstituted C 1 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Condition B2

R 30b is a group represented by *—C(R 34 )(R 35 )(R 36 ),

R 34 to R 36 are each independently a group as defined in Condition B1, at least one of R 34 to R 36 is independently a substituted or unsubstituted C 2 -C 60 alkyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Condition B3

R 30b is 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

14. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1 is one of Compounds 1 to 5, 7 to 8, or 10 to 27:

15. An organic light-emitting device comprising:

a first electrode,

a second electrode; and

an organic layer located between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer, and

wherein the organic layer further comprises at least one of the organometallic compound of claim 1 .

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

the first electrode is an anode,

the second electrode is a cathode,

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

the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

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

18. The organic light-emitting device of claim 17 , wherein

the emission layer further comprises a host, and

an amount of the host in the emission layer is greater than an amount of the organometallic compound in the emission layer.

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

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2025
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 072524/0231 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 13, 2021
From: CHOI, JONGWON; CHO, YONGSUK; KWAK, SEUNGYEON; KIM, SANGDONG; KIM, SOYEON; ARATANI, SUKEKAZU; LEE, SUNGHUN; LEE, JIYOUN; KRAVCHUK, DMITRY
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 056232/0112 →
Priority Claims (2)
KR 10-2020-0057820 · May 14, 2020 · national
KR 10-2021-0061455 · May 12, 2021 · national
Continuity (1)
Related Publication 20210355148A1 · Nov 18, 2021
Cited By (1)
US 12,630,574