IP Library Granted Patent US 12,012,405
Granted Patent B2
US 12,012,405 · App. 17/133,254 · Granted Jun 18, 2024

Compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device

Inventors: Takuya Haruyama (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
C07D471/14H10K85/615H10K85/633H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,012,405
App. No.
17/133,254
Granted
Jun 18, 2024
Kind
B2
Abstract

A novel compound is provided. The novel compound is represented by General Formula (G1). Each of A 1 and A 2 independently represents a substituted or unsubstituted condensed aromatic ring, a substituted or unsubstituted condensed heteroaromatic ring, or a structure represented by Formula (Z-1) or (Z-2); and each of Z 1 and Z 2 independently has a structure represented by Formula (Z-1) or (Z-2), Each of X 1 and X 2 independently represents any one of an alkyl group, a cycloalkyl group, a substituted or unsubstituted cycloalkyl group having a bridge structure, and a trialkylsilyl group. Each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group, and at least one of Ar 1 and Ar 2 includes the same substituent as X 1 . Each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group, a substituted or unsubstituted cycloalkyl group, a trialkylsilyl group, and a substituted or unsubstituted aryl group.

Claims (72)

1. A compound represented by General formula (G1):

wherein in General Formula (G1), each of A 1 and A 2 independently represents a substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms, or a structure represented by General Formula (Z-1) or General Formula (Z-2); and each of Z 1 and Z 2 independently has a structure represented by General Formula (Z-1) or (Z-2),

wherein in General Formula (Z-1), each of X 1 and X 2 independently represents any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and at least one of Ar 1 and Ar 2 represents a substituted aromatic hydrocarbon group having 6 to 13 carbon atoms,

wherein a substituent of the substituted aromatic hydrocarbon group having 6 to 13 carbon is represented by any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and

wherein the substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms represents a condensed heteroaromatic ring including a pyrrole ring, a dibenzofuran ring, or a dibenzothiophene ring.

2. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the compound according to claim 1 .

3. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises a phosphorescent material and the compound according to claim 1 .

4. A lighting device comprising:

the light-emitting device according to claim 2 ; and

at least one of a housing, a cover, and a support base.

5. A compound represented by General formula (G2):

wherein in General Formula (G2), each of B 1 and B 2 independently represents a substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms; and each of Z 1 and Z 2 independently has a structure represented by General Formula (Z-1) or General Formula (Z-2),

wherein in General Formula (Z-1), each of X 1 and X 2 independently represents any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and at least one of Ar 1 and Ar 2 represents a substituted aromatic hydrocarbon group having 6 to 13 carbon atoms,

wherein a substituent of the substituted aromatic hydrocarbon group having 6 to 13 carbon is represented by any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and

wherein the substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms represents a condensed heteroaromatic ring including a pyrrole ring.

6. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the compound according to claim 5 .

7. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises a phosphorescent material and the compound according to claim 5 .

8. A lighting device comprising:

the light-emitting device according to claim 6 ; and

at least one of a housing, a cover, and a support base.

9. A compound represented by General formula (G3):

wherein in General Formula (G3), each of Z 1 and Z 2 independently has a structure represented by General Formula (Z-1) or General Formula (Z-2),

wherein in General Formula (Z-1), each of X 1 and X 2 independently represents any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and at least one of Ar 1 and Ar 2 represents a substituted aromatic hydrocarbon group having 6 to 13 carbon atoms,

wherein a substituent of the substituted aromatic hydrocarbon group having 6 to 13 carbon is represented by any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms, and

wherein each of R 1 to R 42 independently represents any one of hydrogen, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; any one of R 17 to R 29 is bonded to a nitrogen atom that is bonded to Z 1 ; and any one of R 30 to R 42 is bonded to a nitrogen atom that is bonded to Z 2 .

10. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the compound according to claim 9 .

11. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises a phosphorescent material and the compound according to claim 9 .

12. A lighting device comprising:

the light-emitting device according to claim 10 ; and

at least one of a housing, a cover, and a support base.

13. A compound represented by General formula (G4):

wherein in General Formula (G4), each of Z 1 and Z 2 independently has a structure represented by General Formula (Z-1) or General Formula (Z-2),

wherein in General Formula (Z-1), each of X 1 and X 2 independently represents any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms,

wherein each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and at least one of Ar 1 and Ar 2 represents a substituted aromatic hydrocarbon group having 6 to 13 carbon atoms,

wherein a substituent of the substituted aromatic hydrocarbon group having 6 to 13 carbon is represented by any one of an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms, and

wherein each of R 1 to R 17 , R 19 to R 30 , and R 32 to R 42 independently represents any one of hydrogen, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

14. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the compound according to claim 13 .

15. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises a phosphorescent material and the compound according to claim 13 .

16. A lighting device comprising:

the light-emitting device according to claim 14 ; and

at least one of a housing, a cover, and a support base.

17. A compound represented by Structural Formula (100):

18. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the compound according to claim 17 .

19. A light-emitting device comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises a phosphorescent material and the compound according to claim 17 .

20. A lighting device comprising:

the light-emitting device according to claim 18 ; and

at least one of a housing, a cover, and a support base.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: HARUYAMA, TAKUYA; OHSAWA, NOBUHARU; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 054744/0062 →
Priority Claims (1)
JP 2019-239346 · Dec 27, 2019 · national
Continuity (1)
Related Publication 20210206767A1 · Jul 8, 2021