Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10439152-B2
Application number	US-201615389791-A
Country	US
Kind code	B2
Filing date	Dec 23, 2016
Priority date	Mar 2, 2016
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

An organometallic compound represented by Formula 1:

wherein in Formula 1, groups and variables are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,
X 11 is selected from C(R 11 ) and nitrogen atom (N); X 12 is selected from C(R 12 ) and N; X 13 is selected from C(R 13 ) and N; X 14 is selected from C(R 14 ) and N; X 15 is selected from C(R 15 ) and N; X 16 is selected from C(R 16 ) and N; X 17 is selected from C(R 17 ) and N; X 18 is selected from C(R 18 ) and N; X 19 is selected from C(R 19 ) and N; X 20 is selected from C(R 20 ) and N; X 21 is selected from C(R 21 ) and N; X 22 is selected from C(R 22 ) and N;
Z 11 to Z 14 are each independently selected from N and carbon atom (C);
Y 11 and Y 12 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group;
R 11 to R 24 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl 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 1 -C 60 heteroaryl 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —N(Q 3 )(Q 4 ), —B(Q 3 )(Q 4 ), —C(═O)(Q 3 ), —S(═O) 2 (Q 3 ), and —P(═O)(Q 3 )(Q 4 );
provided that two neighboring substituents selected from R 11 to R 24 are optionally linked to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring,
b23 is an integer from 0 to the maximum number of R 23 that can be attached to Y 11 ; and
b24 is an integer from 0 to the maximum number of R 24 that can be attached to Y 12 ;
wherein Q 3 to Q 5 are each independently selected from hydrogen, deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein
X 11 is C(R 11 ); X 12 is C(R 12 ); X 13 is C(R 13 ); X 14 is N; X 15 is C(R 15 ); X 16 is C(R 16 ); X 17 is C(R 17 ); X 18 is C(R 18 ); X 19 is C(R 19 ); X 20 is C(R 20 ); X 21 is C(R 21 ); and X 22 is C(R 22 ); or
X 11 is C(R 11 ); X 12 is C(R 12 ); X 13 is C(R 13 ); X 14 is C(R 14 ); X 15 is C(R 15 ); X 16 is C(R 16 ); X 17 is C(R 17 ); X 18 is C(R 18 ); X 19 is C(R 19 ); X 20 is C(R 20 ); X 21 is C(R 21 ); and X 22 is C(R 22 ).

3. The organometallic compound of claim 1 , wherein
Z 11 is N and Z 12 is C.

4. The organometallic compound of claim 1 , wherein
Z 13 is C and Z 14 is N.

5. The organometallic compound of claim 1 , wherein
Z 11 is N, Z 12 is C, Z 13 is N, and Z 14 is C;
Z 11 is N, Z 12 is C, Z 13 is C, and Z 14 is N;
Z 11 is C, Z 12 is N, Z 13 is N, and Z 14 is C; or
Z 11 is C, Z 12 is N, Z 13 is C, and Z 14 is N.

6. The organometallic compound of claim 1 , wherein
Z 11 is N, Z 12 is C, Z 13 is C, and Z 14 is N.

7. The organometallic compound of claim 1 , wherein
Y 11 and Y 12 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a fluorene group, a pyrrole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, an oxadiazole group, a triazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, an indole group, an iso-indole group, a benzimidazole group, a benzoxazole group, an isobenzoxazole group, an indazole group, a benzofuran group, a benzothiophene group, an indenopyridine group, a carbazole group, a carboline group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, and a benzosilolopyridine group.

8. The organometallic compound of claim 1 , wherein
Y 11 and Y 12 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a fluorene group, an imidazole group, a pyrazole group, a triazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, an indole group, an iso-indole group, a benzimidazole group, an indazole group, a benzofuran group, a benzothiophene group, an indenopyridine group, a carbazole group, a carboline group, a dibenzofuran group, a benzofuranopyridine group, a dibenzothiophene group, a benzothiophenopyridine group, a dibenzosilole group, and a benzosilolopyridine group.

9. The organometallic compound of claim 1 , wherein
Y 11 and Y 12 are each independently selected from a benzene group, a naphthalene group, a fluorene group, an imidazole group, a pyrazole group, a triazole group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, an indole group, an iso-indole group, a benzimidazole group, an indazole group, an indenopyridine group, a carbazole group, a carboline group, a dibenzofuran group, a benzofuranopyridine group, a dibenzothiophene group, a benzothiophenopyridine group, a dibenzosilole group, and a benzosilolopyridine group.

10. The organometallic compound of claim 1 , wherein
at least one selected from Y 11 and Y 12 is selected from a C 1 -C 60 heterocyclic group.

11. The organometallic compound of claim 1 , wherein
moieties represented by Y 11 -Y 12 are selected from Formulae 3-1 to 3-29:

wherein, in Formulae 3-1 to 3-29,
X 31 is selected from C(R 40 )(R 41 ), N(R 41 ), O, S, and Si(R 40 )(R 41 );
R 31 to R 41 are each independently selected from hydrogen, deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CFH 2 , —CF 2 H, —CF 3 , and a benzyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a b

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Banglin
• Lee Kum Hee
• Lee Sunyoung
• Choi Hyeonho

Classifications

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title