IP Library Granted Patent US 12,448,403
Granted Patent B2
US 12,448,403 · App. 17/592,639 · Granted Oct 21, 2025

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

Inventors: Kum Hee Lee (Suwon-si, KR); Byungjoon Kang (Seoul, KR); Seungyeon Kwak (Suwon-si, KR); Sangdong Kim (Seongnam-si, KR); Sungmin Kim (Incheon, KR); Yong Joo Lee (Suwon-si, KR); Jeoungin Yi (Seoul, KR); Byoungki Choi (Hwaseong-si, KR); Kyuyoung Hwang (Anyang-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07F15/0033H10K85/342H10K50/12H10K50/15H10K50/16H10K50/171H10K50/18
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Quick Facts
Patent No.
US 12,448,403
App. No.
17/592,639
Granted
Oct 21, 2025
Kind
B2
Abstract

An organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device: M(L 1 ) n1 (L 2 ) n2   Formula 1 wherein, in Formula 1, M is a transition metal, L 1 is a ligand represented by Formula 2-1, L 2 is a ligand represented by Formula 2-2, n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and L 1 is different from L 2 .

Claims (171)

1. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2   Formula 1

wherein, in Formula 1,

M is iridium,

L 1 is a ligand represented by Formula 2-1,

L 2 is a ligand represented by Formula 2-2,

n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and

L 1 is different from L 2 :

wherein, in Formulae 2-1 and 2-2,

Y 2 is C, and Y 3 is N,

ring CY 2 is a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group,

ring CY 3 is a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a naphthoquinoline group, a naphthoisoquinoline group, a naphthoquinoxaline group, a pyridoquinoline group, a pyridoisoquinoline group, a pyridoquinoxaline group, a pyridine group condensed with a cyclohexane group, an imidazole group, a benzimidazole group, a naphthoimidazole group, a phenanthrenoimidazole group, or a pyridoimidazole group,

ring CY 41 , ring CY 42 and ring CY 43 are each independently i) A group, ii) a polycyclic group in which at least two A groups are condensed, or iii) a polycyclic group in which at least one A group and at least one B group are condensed,

wherein A group is a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group and B group is a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, or a silole group,

wherein a carbon atom in ring CY 41 in Formula 2-2 is bound to M in Formula 1 via a covalent bond, X 11 is Si or Ge,

T 3 is a single bond, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

X 4 is O, S, Se, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ),

R 1 to R 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, 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 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 ),

R 4 , R 14 , R 15 , R 16 , R 48 , and R 49 are each independently hydrogen, deuterium, —F, —SF 5 , 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 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, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,

a1 is an integer from 0 to 3,

a2 is an integer from 0 to 8,

a3 and a4 are each independently an integer from 0 to 10,

when a1 is 2 or 3, at least two of the R 1 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a2 is 2 to 8, at least two of the R 2 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a3 is 2 to 10, at least two of the R 3 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a4 is 2 to 10, at least two of the R 4 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a has a same definition as R 2 ,

* and *′ each indicate a binding site to M in Formula 1, 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 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, or 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, 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, 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 ), —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 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, 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, 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 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; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 60 alkyl 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, or any combination thereof.

2. The organometallic compound of claim 1 , wherein ring CY 2 is a benzene group a naphthalene group.

3. The organometallic compound of claim 1 , wherein ring CY 3 is a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, group, a pyridine group condensed with a cyclohexane group, an imidazole group, a benzimidazole group, a naphthoimidazole group, group, or a pyridoimidazole group.

4. The organometallic compound of claim 1 , wherein ring CY 41 and ring CY 42 are each independently a benzene group, a naphthalene group, or a benzene group condensed with a norbornane group, and

ring CY 43 is:

a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, or a chrysene group; or

a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, or a chrysene group, each condensed with a norbornane group.

5. The organometallic compound of claim 1 , wherein T 3 is:

a single bond; or

a C 1 -C 20 alkylene group, a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each 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 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 phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.

6. The organometallic compound of claim 1 , wherein R 1 to R 4 , R 48 , and R 49 are each independently:

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

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each 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 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 phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, and

R 14 to R 16 are each independently a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each 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 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 phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.

7. The organometallic compound of claim 1 , wherein the organometallic compound comprises deuterium, a fluoro group, or any combination thereof and at least one of Conditions 3 to 8 is satisfied:

Condition 1

at least one of the R 1 moieties, the number a1 representing a count of the R 1 moieties, may not be hydrogen and may include at least one deuterium,

Condition 2

at least one of the R 2 moieties, the number a2 representing a count of the R 2 moieties, may not be hydrogen and may include at least one deuterium,

Condition 3

at least one of the *-T 3 -R 3 moieties, the number a3 representing a count of the *-T 3 -R 3 moieties, may not be hydrogen and may include at least one deuterium,

Condition 4

at least one of the R 4 moieties, the number a4 representing a count of the R 4 moieties, may not be hydrogen and may include at least one deuterium,

Condition 5

at least one of the R 1 moieties (the number a1 representing a count of the R 1 moieties) may not be hydrogen and may include at least one fluoro group,

Condition 6

at least one of the R 2 moieties, the number a2 representing a count of the R 2 moieties, may not be hydrogen and may include at least one fluoro group,

Condition 7

at least one of the *-T 3 -R 3 moieties, the number a3 representing a count of the *-T 3 -R 3 moieties, may not be hydrogen and may include at least one fluoro group, and

Condition 8

at least one of R 4 moieties, the number a4 representing a count of the R 4 moieties, may not be hydrogen and may include at least one fluoro group.

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

in Formula 2-1 is represented by one of Formulae CY1-1 or CY1-2:

wherein, in Formulae CY1-1 and CY1-2,

X 11 , R 14 to R 16 , and R 10a are respectively understood by referring to the descriptions of X 11 , R 14 to R 16 , and R 10a in claim 1 ,

R 11 to R 13 each has a same definition as R 1 ,

a14 is an integer from 0 to 4,

*′ indicates a binding site to M in Formula 1, and

*″ indicates a binding site to an adjacent atom in Formula 2-1.

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

in Formula 2-1 is represented by one of Formulae CY2-1, CY2-11, CY2-14, CY2-17, and CY2-20 to CY2-25:

wherein, in Formulae CY2-1, CY2-11, CY2-13, CY2-14, CY2-16, CY2-17, CY2-19, and CY2-20 to CY2-25,

Y 2 is understood by referring to the description of Y 2 in claim 1 ,

X 2 is O, S, Se, N(R 28 ), C(R 28 )(R 29 ), or Si(R 28 )(R 29 ),

R 28 and R 29 are each understood by referring to the description of R 2 claim 1 ,

*″ indicates a binding site to an adjacent atom in Formula 2-1, and

*indicates a binding site to M in Formula 1.

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

in Formula 2-2 is represented by one of Formulae CY3-3, CY3-5 to CY3-11, CY3-14, CY-17, CY-20 to CY3-34, CY3-37, CY3-38, CY3-40 to CY3-42, CY3-44 to CY3-46 and CY3-48:

wherein, in Formulae CY3-3, CY3-5 to CY3-11, CY3-13, CY3-14, CY3-16 to CY3-34, CY3-37, CY3-38, CY3-40 to CY3-42, CY3-44 to CY3-46 and CY3-48,

X 3 is N(T 3 -R 3 ),

Y 3 , T 3 , and R 3 are respectively understood by referring to the descriptions of Y 3 , T 3 , and R 3 in claim 1 ,

*′ indicates a binding site to M in Formula 1, and

*″ indicates a binding site to an adjacent atom in Formula 2-2.

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

in Formula 2-2 is represented by one of Formulae CY4-1 to CY4-6:

wherein, in Formulae CY4-1 to CY4-6,

X 4 , ring CY 42 , and ring CY 43 are respectively understood by referring to the descriptions of X 4 , ring CY 42 , and ring CY 43 in claim 1 ,

Z 1 to Z 4 are each independently N or C,

* indicates a binding site to M in Formula 1, and

*″ indicates a binding site to ring CY 3 in Formula 2-2.

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

in Formula 2-2 is represented by one of Formulae CY401 to CY412:

wherein, in Formulae CY401 to CY412,

X 4 is understood by referring to the description of X 4 in claim 1 ,

Z 5 to Z 8 and Z 11 to Z 18 are each independently N or C, and

an X 4 -containing 5-membered ring is condensed to an adjacent ring CY 41 .

13. 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 the organometallic compound of claim 1 .

14. The organic light-emitting device of claim 13 , 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.

15. The organic light-emitting device of claim 13 , wherein the emission layer comprises the organometallic compound.

16. The organic light-emitting device of claim 15 , wherein the emission layer is configured to emit green light.

17. The organic light-emitting device of claim 15 , wherein the emission layer further comprises a host in an amount greater than an amount of the organometallic compound.

18. An electronic apparatus comprising the organic light-emitting device of claim 13 .

19. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2   Formula 1

wherein, in Formula 1,

M is iridium,

L 1 is a ligand represented by Formula 2-1,

L 2 is a ligand represented by Formula 2-2,

n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and

L 1 is different from L 2 :

wherein, in Formulae 2-1 and 2-2,

Y 2 is C, and Y 3 is N,

ring CY 2 is a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group,

ring CY3 is a pyridine group,

ring CY 41 , ring CY 42 , and ring CY 43 are each independently i) A group, ii) a polycyclic group in which at least two A groups are condensed, or iii) a polycyclic group in which at least one A group and at least one B group are condensed,

wherein A group is a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group and B group is a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, or a silole group,

wherein a carbon atom in ring CY 41 in Formula 2-2 is bound to M in Formula 1 via a covalent bond,

wherein a group represented by

 in Formula 2-2 is represented by one of Formulae CY4-1 to CY4-3, CY4-5 and CY4-6:

wherein, in Formulae CY4-1 to CY4-3, CY4-5 and CY4-6,

Z 1 to Z 4 are each independently N or C,

* indicates a binding site to M in Formula 1, and *″ indicates a binding site to ring CY 3 in Formula 2-2,

X 11 is Si or Ge,

T 3 is a single bond, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

X 4 is O, S, Se, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ),

R 1 to R 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, 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 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 ),

R 4 , R 14 , R 15 , R 16 , R 48 , and R 49 are each independently hydrogen, deuterium, —F, —SF 5 , 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 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, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,

a1 is an integer from 0 to 3,

a2 is an integer from 0 to 8,

a3 and a4 are each independently an integer from 0 to 10,

when a1 is 2 or 3, at least two of the R 1 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a2 is 2 to 8, at least two of the R 2 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a3 is 2 to 10, at least two of the R 3 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

when a4 is 2 to 10, at least two of the R 4 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a has a same definition as R 2 ,

* and *′ each indicate a binding site to M in Formula 1, 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 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, or 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, 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, 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 ), —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 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, 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, 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 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; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 60 alkyl 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, or any combination thereof.

20. The organometallic compound of claim 19 , wherein a group represented by

in Formula 2-2 is represented by one of Formulae CY3(1) to CY3(16):

wherein, in Formulae CY3(1) to CY3(16),

Y 3 is understood by referring to the description of Y 3 in claim 19 ,

R 31 to R 34 each has a same definition as R 3 , with the proviso that R 31 to R 34 are each not hydrogen,

*′ indicates a binding site to M in Formula 1, and

*″ indicates a binding site to an adjacent atom in Formula 2-2.

21. 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 the organometallic compound of claim 19 .

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 Feb 4, 2022
From: LEE, KUM HEE; KANG, BYUNGJOON; KWAK, SEUNGYEON; KIM, SANGDONG; KIM, SUNGMIN; LEE, YONG JOO; YI, JEOUNGIN; CHOI, BYOUNGKI; HWANG, KYUYOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 058886/0473 →
Priority Claims (2)
KR 10-2021-0019354 · Feb 10, 2021 · national
KR 10-2022-0014726 · Feb 4, 2022 · national
Continuity (1)
Related Publication 20220259237A1 · Aug 18, 2022
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