IP Library Granted Patent US 12,391,713
Granted Patent B2
US 12,391,713 · App. 16/830,660 · Granted Aug 19, 2025

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

Inventors: Sangdong Kim (Seongnam-si, KR); Seungyeon Kwak (Suwon-si, KR); Sungjun Kim (Seongnam-si, KR); Jongsoo Kim (Suwon-si, KR); Aram Jeon (Seoul, KR); Sunggyu Kang (Suwon-si, KR); Hyun Koo (Seongnam-si, KR); Jiwhan Kim (Seoul, KR); Sukekazu Aratani (Hwaseong-si, KR); Kum Hee Lee (Suwon-si, KR); Yongsuk Cho (Hwaseong-si, KR); Yuri Cho (Suwon-si, KR); Byoungki Choi (Hwaseong-si, KR); Jongwon Choi (Yongin-si, KR); Hyeonho Choi (Seoul, KR); Youngki Hong (Anyang-si, KR); Kyuyoung Hwang (Anyang-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07F15/0033C09K11/06H10K85/342C09K2211/185H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,391,713
App. No.
16/830,660
Granted
Aug 19, 2025
Kind
B2
Abstract

Disclosed are an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device: The detailed description of Formula 1 is the same as described in the present specification.

Claims (90)

1. An organometallic compound represented by Formula 1 below:

wherein, in Formula 1,

Y 2 is C,

a group represented by

in Formula 1 is a group represented by one of Formulae A(1) to A(10),

wherein,

R 10 and R 12 in Formula A(1) are hydrogen,

R 9 and R 11 in Formula A(1) are each independently a group represented by Formula 2-2, deuterium, 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 2 -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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

X 21 in Formulae A(6) to A(10) is O, S, N(R 25 ), or Si(R 25 )(R 26 ),

R 9 to R 12 and R 21 to R 26 in Formulae A(2) to A(10) are each independently a group represented by Formula 2-2, hydrogen, deuterium, —F, 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 2 -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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, provided that, i) at least one of R 9 , R 10 , R 21 and R 24 in Formula A(2) is not hydrogen, ii) at least one of R 9 , R 12 , R 21 and R 24 in Formula A(3) is not hydrogen, and iii) at least one of R 11 , R 12 , R 21 and R 24 in Formula A(4) is not hydrogen,

*′ in Formulae A(1) to A(10) is a binding site to Ir in Formula 1, and

*″ in Formulae A(1) to A(10) is a binding site to a neighboring atom in Formula 1,

R 1 to R 8 , and A 1 to A 7 are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, 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 2 -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 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),

*—Si(Z 1 )(Z 2 )(Z 3 )  Formula 2-1

*—Ge(Z 11 )(Z 12 )(Z 13 )  Formula 2-2

Z 1 to Z 3 and Z 11 to Z 13 in Formulae 2-1 and 2-2 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 2 -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 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ) or —P(Q 8 )(Q 9 ), and * indicates a binding site to a neighboring atom,

a2 is an integer of 0 to 20, wherein, when a2 is 2 or more, two or more of R 20 (s) are identical to or different from each other,

at least one of R 3 to R 6 is independently a group represented by Formula 2-1 or a group represented by Formula 2-2,

two or more of R 1 to R 8 are optionally linked together to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,

two or more R 9 to R 12 and R 21 to R 26 in Formulae A(2) to A(10) are optionally linked together to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one Ria or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,

two or more of A 1 to A 7 are optionally linked together to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,

R 1a is the same as described in connection with A 7 ,

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 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl 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 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 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, or a C 1 -C 60 alkylthio group;

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, or a C 1 -C 60 alkylthio 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 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 2 -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 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any 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 2 -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 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 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 1 -C 60 alkylthio group C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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 ), —Ge(Q 23 )(Q 24 ) (Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or any 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

any 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 any 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 2 -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 any combination thereof; 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; or a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein R 1 to R 8 , and A 7 in Formula 1 are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, —F, a substituted or unsubstituted C 1 -C 20 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 phenyl group, or a substituted or unsubstituted biphenyl group, and

Z 1 to Z 3 and Z 11 to Z 13 in Formula 2 are each independently hydrogen, deuterium, —F, a substituted or unsubstituted C 1 -C 20 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 phenyl group, or a substituted or unsubstituted biphenyl group.

3. The organometallic compound of claim 1 , wherein R 1 to R 8 and A 7 in Formula 1 are each independently:

a group represented by Formula 2-1 or a group represented by Formula 2-2;

hydrogen, deuterium, or —F; or

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

R 9 and R 11 in Formula A(1) are each independently:

a group represented by Formula 2-1 or a group represented by Formula 2-2; or

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated 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 (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated a phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated a biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, or any combination thereof, and

R 9 to R 12 and R 21 to R 26 in Formulae A(2) to A(10) are each independently:

a group represented by Formula 2-1 or a group represented by Formula 2-2;

hydrogen, deuterium, or —F; or

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated 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 (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated a phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated a biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, or any combination thereof.

4. The organometallic compound of claim 1 , wherein at least one of R 3 to R 6 in Formula 1 is a group represented by Formula 2-2.

5. The organometallic compound of claim 1 , wherein at least one of R 3 and R 5 in Formula 1 is independently a group represented by Formula 2-1 or a group represented by Formula 2-2.

6. The organometallic compound of claim 1 , wherein, at least one of the R 3 to R 6 which is not the group represented by Formula 2-1 or Formula 2-2 is independently:

—F; or

a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, or a fluorinated a biphenyl group, each unsubstituted or substituted with deuterium, —F, C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl 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 a phenyl group, a fluorinated a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated a biphenyl group, a fluorinated a biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, or any combination thereof.

7. The organometallic compound of claim 1 , wherein, at least one of R 3 to R 6 which is not the group represented by Formula 2-1 or Formula 2-2 is each independently:

deuterium; or

a deuterated C 1 -C 20 alkyl group, a deuterated C 3 -C 10 cycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a deuterated a phenyl group, or a deuterated a biphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated 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 (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated a phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a deuterated a biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, or any combination thereof.

8. The organometallic compound of claim 1 wherein, at least one of R 3 to R 6 which is not the group represented by Formula 2-1 or Formula 2-2 is each independently:

hydrogen; or

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with a C 1 -C 20 alkylgroup, a 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 (C 1 -C 20 alkyl)C 1 -C 10 heterocycloalkyl group, a phenyl group, a (C 1 -C 20 alkyl) phenyl group, a biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof.

9. The organometallic compound of claim 1 , wherein the organometallic compound satisfies at least one of Condition 1 to Condition 3:

Condition 1

A 1 to A 6 in Formula 1 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 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,

Condition 2

at least one of A 1 to A 6 in Formula 1 is 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 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

Condition 3

A 7 in Formula 1 is 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 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.

10. The organometallic compound of claim 1 , wherein the organometallic compound satisfies at least one of Condition 4 and Condition 5:

Condition 4

two or more of A 1 to A 3 in Formula 1 are linked together, and thus a group represented by *—C(A 1 )(A 2 )(A 3 ) is a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a , and

Condition 5

two or more of A 4 to A 6 in Formula 1 are linked together, and thus a group represented by *—C(A 4 )(A 5 )(A 6 ) is a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a .

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

in Formula 1 is a group represented by one of Formulae CY1 to CY24, CY41 to CY48 and CY57 to CY108

wherein, in Formulae CY1 to CY24, CY41 to CY48, and CY57 to CY108,

T 3 to T 6 are each independently a group represented by Formula 2-1 or a group represented by Formula 2-2,

R 2 to R 22 and R 1a are the same as described in claim 1 , and R 2 to R 8 are not hydrogen,

* is a binding site to Ir in Formula 1, and

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

12. The organometallic compound of claim 11 , wherein a group represented by

in Formula 1 is a group represented by Formula CY9, CY11, CY12, CY14, or CY76.

13. The organometallic compound of claim 1 , wherein R 9 and R 11 in Formula A(1) are each independently: a C 1 -C 20 alkyl group or a deuterated C 1 -C 20 alkyl group.

14. The organometallic compound of claim 1 , wherein the organometallic compound is at least one of Compounds 1 to 8, 10 and 12 to 16 below:

15. 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 and comprising an emission layer,

wherein the organic layer comprises at least one 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 between the first electrode and the emission layer and an electron transport region 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 any combination thereof, and

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

17. The organic light-emitting device of claim 15 , wherein the organometallic compound is included in the emission layer.

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

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2025
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 072945/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2020
From: KIM, SANGDONG; KWAK, SEUNGYEON; KIM, SUNGJUN; KIM, JONGSOO; JEON, ARAM; KANG, SUNGGYU; KOO, HYUN; KIM, JIWHAN; ARATANI, SUKEKAZU; LEE, KUM HEE; CHO, YONGSUK; CHO, YURI; CHOI, BYOUNGKI; CHOI, JONGWON; CHOI, HYEONHO; HONG, YOUNGKI; HWANG, KYUYOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 052246/0189 →
Priority Claims (2)
KR 10-2019-0037217 · Mar 29, 2019 · national
KR 10-2020-0036054 · Mar 25, 2020 · national
Continuity (1)
Related Publication 20200308203A1 · Oct 1, 2020
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