IP Library Granted Patent US 11,937,496
Granted Patent B2
US 11,937,496 · App. 16/831,696 · Granted Mar 19, 2024

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

Inventors: Soyeon Kim (Seoul, KR); Jiyoun Lee (Anyang-si, KR); Yongsuk Cho (Hwaseong-si, KR); Jongwon Choi (Yongin-si, KR); Dmitry Kravchuk (Hwaseong-si, KR); Banglin Lee (Suwon-si, KR); Yoonhyun Kwak (Seoul, KR); Hyun Koo (Seongnam-si, KR); Seokhwan Hong (Seoul, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H10K85/342C07F15/0033C09K11/06C09K2211/1029C09K2211/185H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18H10K2101/10
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Quick Facts
Patent No.
US 11,937,496
App. No.
16/831,696
Granted
Mar 19, 2024
Kind
B2
Abstract

Provided is an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device. Ir(L 1 )(L 2 )(L 3 )  Formula 1 L 1 to L 3 in Formula 1 are the same as described in the present specification.

Claims (121)

1. An organometallic compound represented by Formula 1:

Ir(L 1 )(L 2 )(L 3 )  Formula 1

wherein, in Formula 1, L 1 is a ligand represented by Formula 1-1, L 2 is a ligand represented by Formula 1-2, L 3 is a ligand represented by Formula 1-3, and L 1 and L 2 are different from each other:

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

Y 2 is C,

Y 11 and Y 12 are each independently C or N,

ring CY 2 , ring CY 11 , and ring CY 12 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

R 1 to R 8 , R 20 , Z 1 , Z 2 , and A 1 to A 7 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 ),

a2, b1, and b2 are each independently an integer from 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, when b1 is 2 or more, two or more of Z 1 (s) are identical to or different from each other, and when b2 is 2 or more, two or more of Z 2 (s) are identical to or different from each other,

at least one of R 1 to R 8 and/or at least one of R 20 (s) in the number of a2 is a fluoro group (—F) or a fluorinated group,

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 of R 20 (s) in the number of a2 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 of Z 1 (s) in the number of b1 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 of Z 2 (s) in the number of b2 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 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 ,

* and *′ each indicate a binding site to Ir in Formula 1,

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 independently:

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 ), or —P(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 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 ), or —P(Q 28 )(Q 29 );

—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, or a C 6 -C 60 aryl 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 2 -C 10 heterocycloalkenyl group; or a C 6 -C 60 aryl group which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, or 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,

wherein the group represented by

 in Formula 1-1 is represented by one of Formulae A(1) to A(10):

wherein, in Formulae A(1) to A(10),

Y 2 is C,

X 21 is O, S, N(R 25 ), C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 9 to R 12 and R 21 to R 26 are the same as described in connection with R 20 ,

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

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

wherein the group represented by

 in Formula 1-2 is a group represented by one of Formulae CY12-1 to CY12-22:

wherein, in Formulae Formulae CY12-1 to CY12-22,

Y 12 is C,

X 2 is O, S, N(Z 25 ), C(Z 25 )(Z 26 ), or Si(Z 25 )(Z 26 ),

Z 25 and R 26 are the same as described in connection with Z 2 ,

* and *′ each indicate a binding site to Ir in Formula 1, and

each *″ indicates a binding site to a neighboring atom.

2. The organometallic compound of claim 1 , wherein ring CY 2 , ring CY 11 , and ring CY 12 in Formulae 1-1 and 1-2 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a pyridine group condensed with a cyclohexane group, a pyridine group condensed with an adamantane group, a benzene group condensed with an adamantane group, a benzene group condensed with a pyridine group, a benzene group condensed with a quinoline group, or a benzene group condensed with an isoquinoline group.

3. The organometallic compound of claim 1 , wherein R 1 to R 8 , R 20 , Z 1 , Z 2 and A 1 to A 7 in Formulae 1-1 to 1-3 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, a substituted or unsubstituted biphenyl group, —Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ),

wherein a substituent of the substituted C 1 -C 20 alkyl group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the phenyl group and the biphenyl 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 ), or —P(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 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 ), or —P(Q 28 )(Q 29 ); or

—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 );

wherein Q 3 to Q 5 , 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, or 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, or 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.

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

hydrogen, deuterium, or —F;

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 biphenyl group, a fluorinated biphenyl group, or a (C 1 -C 20 alkyl)biphenyl group; or

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

R 20 , Z 1 and Z 2 in Formulae 1-1 and 1-2 are each independently:

hydrogen or deuterium;

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 substituted 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 biphenyl group, or a (C 1 -C 20 alkyl)biphenyl group; or

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

5. The organometallic compound of claim 1 , wherein at least one of R 4 to R 7 in Formula 1-1 is each independently a fluoro group (—F) or a fluorinated group.

6. The organometallic compound of claim 1 , wherein at least one of R 1 to R 8 in Formula 1-1 is:

—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 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 biphenyl group, a fluorinated biphenyl group, or a (C 1 -C 20 alkyl)biphenyl group.

7. The organometallic compound of claim 1 , wherein at least one of Z 1 and Z 2 of Formula 1-2 is each independently:

deuterium;

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 biphenyl group, or a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof, or

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

8. The organometallic compound of claim 1 , wherein at least one of Condition 1, Condition 2, and Condition 3, or a combination thereof is satisfied:

Condition 1

A 1 to A 6 of Formula 1-3 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 of Formula 1-3 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,

Condition 3

A 7 of Formula 1-3 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.

9. The organometallic compound of claim 1 , wherein at least one of Condition 4 and Condition 5 is satisfied:

Condition 4

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

Condition 5

two or more of A 4 to A 6 of Formula 1-3 are linked together so that a group represented by *—C(A 4 )(A 5 )(A 6 ) becomes 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 .

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

in Formula 1-1 is represented by one of Formulae CY1 to CY112:

wherein, in Formulae CY1 to CY112,

T 2 to T 8 are each independently a fluoro group or a fluorinated group,

R 1a is the same as described in claim 1 ,

R 2 is R 2 ′, R 3 is R 3 ′, R 4 is R 4 ′, R 5 is R 5 ′, R 6 is R 6 ′, R 7 is R 7 ′, and R 8 is R 8 ′, wherein R 2 ′ to R 8 ′ are each independently 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 ), wherein Q 1 to Q 9 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, or 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, or 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,

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

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

11. The organometallic compound of claim 10 , wherein a group represented by

in Formula 1-1 is represented by one of Formula CY1, CY9, CY11, CY17, CY19, CY25, CY30, CY57, CY64, or CY85.

12. The organometallic compound of claim 1 , wherein R 9 and R 11 in Formula A(1) are each independently:

deuterium; 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 substituted 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 biphenyl group, or a (C 1 -C 20 alkyl)biphenyl group, or any combination thereof.

13. The organometallic compound of claim 1 , wherein the group represented by

in Formula 1-2 is a group represented by one of Formulae CY11-1 to CY11-16,

wherein, in Formulae CY11-1 to CY11-16,

Y 11 is N,

* and *′ each indicate a binding site to Ir in Formula 1, and

each *″ indicates a binding site to a neighboring atom.

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

in Formula 1-2 is a group represented by one of Formulae CY11(1) to CY11(22) and CY11-8 to CY11-16, and

a group represented by

 in Formula 1-2 is a group represented by one of Formulae CY12 (1) to CY12-(16) and CY12-8 to CY12-22:

wherein, in Formulae CY11(1) to CY11(16), CY11-8 to CY11-16, CY12(1) to CY12-(16) and CY12-8 to CY12-22,

Y 11 is N,

Y 12 is C,

X 2 is O, S, N(Z 25 ), C(Z 25 )(Z 26 ), or Si(Z 25 )(Z 26 ),

Z 11 to Z 16 are the same as described in connection with Z 1 in claim 1 , and each of Z 11 to Z 16 is not hydrogen,

Z 21 to R 26 are the same as described in connection with Z 2 in claim 1 and each of Z 21 to Z 24 is not hydrogen,

* and *′ each indicate a binding site to Ir in Formula 1, and

each *″ indicates a binding site to a neighboring atom.

15. The organometallic compound of claim 1 , wherein the organometallic compound is one of Compounds 1 to 27:

16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer 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 .

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

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region 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, or a buffer layer, or any combination thereof, and

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

18. The organic light-emitting device of claim 16 , wherein the organometallic compound is included in the emission layer.

19. An apparatus comprising the organic light-emitting device of claim 16 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2025
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 072524/0231 →
CORRECTIVE ASSIGNMENT TO CORRECT THE EXECUTION DATES FOR INVENTORS 1, 3, 6, 8-9. ASSIGNOR'S PREVIOUSLY RECORDED ON REEL 052246 FRAME 0224. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Apr 20, 2020
From: KIM, SOYEON; LEE, JIYOUN; CHO, YONGSUK; CHOI, JONGWON; KRAVCHUK, DMITRY; LEE, BANGLIN; KWAK, YOONHYUN; KOO, HYUN; HONG, SEOKHWAN
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 052739/0452 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2020
From: KIM, SOYEON; LEE, JIYOUN; CHO, YONGSUK; CHOI, JONGWON; KRAVCHUK, DMITRY; LEE, BANGLIN; KWAK, YOONHYUN; KOO, HYUN; HONG, SEOKHWAN
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 052246/0224 →
Priority Claims (2)
KR 10-2019-0037216 · Mar 29, 2019 · national
KR 10-2020-0036053 · Mar 25, 2020 · national
Continuity (1)
Related Publication 20200313097A1 · Oct 1, 2020