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

Patent metadata

Field	Value
Publication number	US-12588405-B2
Application number	US-202318241749-A
Country	US
Kind code	B2
Filing date	Sep 1, 2023
Priority date	Sep 7, 2022
Publication date	Mar 24, 2026
Grant date	Mar 24, 2026

Abstract

Provided are an organometallic compound represented by Formula 1, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device. The first ligand, L1, of the organometallic compound may include a first polycyclic coordinate ring in which four or more rings are condensed with each other and a second polycyclic coordinate ring in which three or more rings are condensed with each other. M1(L1)n1(L2)n2  Formula 1.

First claim

What is claimed is:

1 . An organometallic compound represented by Formula 1:
M 1 ( L 1 ) n1 ( L 2 ) n2 ,  Formula 1
wherein, in Formula 1, M 1 is a transition metal, L 1 is a ligand represented by Formula 1A, L 2 is a bidentate ligand, and n1 and n2 are each independently 1 or 2,

wherein, in Formula 1A,
X 1 is C or N, X 2 is C or N,
ring CY 1 and ring CY 2 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
ring CY 1 is a polycyclic group in which four or more rings are condensed with each other,
R 1 and R 2 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkylthio group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 6 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
a1 and a2 are each independently an integer from 1 to 10,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl, a C 2 -C 60 alkenyl group, a C 2 -C 60 group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

2 . The organometallic compound of claim 1 , wherein a part represented by

in Formula 1A is a group represented by any one selected from Formulae CY1(1) to CY1(4):

wherein, in Formulae CY1(1) to CY1(4),
ring CY 11 and ring CY 12 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 1 is C or N,
Y 1 is O, S, Se, N(R 1a ), C(R 1a )(R 1b ), or Si(R 1a )(R 1b ),
Y 2 is O, S, Se, N(R 1c ), C(R 1c )(R 1d ), or Si(R 1c )(R 1d ),
R 11 , R 12 , R 1a , R 1b , R 1c , and R 1d are each independently as described with respect to R 1 in Formula 1,
a11 and a12 are each independently an integer from 1 to 10, and
and *″ each indicate a binding site to a neighboring atom.

3 . The organometallic compound of claim 1 , wherein a part represented by

in Formula 1A is a group represented by any one selected from Formulae CY1(1A) to CY1(4A):

wherein, in Formulae CY1(1A) to CY1(4A),
X 1 is C or N,
Y 1 is O, S, Se, N(R 1a ), C(R 1a )(R 1b ), or Si(R 1a )(R 1b ),
Y 2 is O, S, Se, N(R 1c ), C(R 1c )(R 1d ), or Si(R 1c )(R 1d ),
R 13 , R 14 , R 1a , R 1b , R 1c , and R 1d are each independently as described with respect to R 1 in Formula 1,
a13 and a14 are each independently an integer from 1 to 4, and
and *″ each indicate a binding site to a neighboring atom.

4 . The organometallic compound of claim 1 , wherein ring CY 2 is i) a polycyclic group in which two or more cyclic groups selected from Group A1 are condensed with each other, ii) a polycyclic group in which two or more cyclic groups selected from Group A2 are condensed with each other, or iii) a polycyclic group in which at least one cyclic group selected from Group A1 and at least one cyclic group selected from Group A2 are condensed with each other:
Group A1: a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isooxazole group, an oxadiazole group, an isooxadiazole group, an oxatriazole group, an isooxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group, Group A2: an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group.

5 . The organometallic compound of claim 1 , wherein a part represented by

in Formula 1A is a group represented by any one selected from Formulae CY2(1) to CY2(5):

wherein, in Formulae CY2(1) to CY2(5),
X 2 is C or N,
X 11 is C(Z 11 ) or N, X 12 is C(Z 12 ) or N, X 13 is C(Z 13 ) or N, X 14 is C(Z 14 ) or N,
X 21 is C(Z 21 ) or N, X 22 is C(Z 22 ) or N, X 23 is C(Z 23 ) or N, X 24 is C(Z 24 ) or N,
Y 3 is O, S, Se, N(R 3a ), C(R 3a )(R 3b ), Si(R 3a )(R 3b ), or Ge(R 3a )(R 3b ),
R 21 , R 22 , Z 11 to Z 14 , Z 21 to Z 24 , R 3a , and R 3b are each independently as described with respect to R 2 in Formula 1, and
and *″ each indicate a binding site to a neighboring atom.

Assignees

• Samsung Display Co Ltd

Inventors

• Yoo Dongsun
• Kang Donguk
• Kim Gyeongheon
• Kim Seran
• KIM Sohae
• Kim Jihye
• Kim Hoilim
• Park Saerom
• Shim Yongsub

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title