IP Library › Granted Patent US 10,305,044
Granted Patent B2
US 10,305,044 · App. 15/097,520 · Granted May 28, 2019

Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Satoshi Seo (Kanagawa, JP); Yuko Kubota (Kanagawa, JP); Tatsuyoshi Takahashi (Kanagawa, JP); Satomi Mitsumori (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0067C07D401/14C07D403/14C09K11/06H01L51/0072C09K2211/1007C09K2211/1029C09K2211/1044H01L51/5016H01L51/5072H01L2251/5338H01L2251/5361
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Quick Facts
Patent No.
US 10,305,044
App. No.
15/097,520
Granted
May 28, 2019
Kind
B2
Abstract

A novel heterocyclic compound is provided. A highly efficient and reliable light-emitting element is provided. The heterocyclic compound is represented by a general formula (G1). In the general formula (G1), any one, two, or three of Y 1 to Y 4 in a ring A represent N atoms, and the rest of Y 1 to Y 4 represents CH. In the case where any two or three of the Y 1 to Y 4 are N atoms, the N atoms are not next to each other. Further, Ar 1 represents a substituted or unsubstituted biphenyldiyl group, Ar 2 represents a substituted or unsubstituted biphenyldiyl group, Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton, Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton, the carbazole skeleton included in the Cz 1 is directly bonded to the Ar 1 , and the carbazole skeleton included in the Cz 2 is directly bonded to the Ar 2 .

Claims (85)

1. A heterocyclic compound represented by a general formula (G1):

wherein each of any one, two, or three of Y 1 to Y 4 in a ring A represents N, and each of the rest of Y 1 to Y 4 represents CH,

wherein in the case where each of any two or three of the Y 1 to Y 4 is N, the N of the any two or three of the Y 1 to Y 4 are not next to each other,

wherein Ar 1 represents a substituted or unsubstituted biphenyldiyl group,

wherein Ar 2 represents a substituted or unsubstituted biphenyldiyl group,

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 is directly bonded to the Ar 1 , and

wherein the carbazole skeleton included in the Cz 2 is directly bonded to the Ar 2 .

2. A heterocyclic compound represented by a general formula (G1):

wherein each of any one or two of Y 1 to Y 4 in a ring A represents N, and each of the rest of Y 1 to Y 4 represents CH,

wherein in the case where each of two of the Y 1 to Y 4 is N , each of Y 1 and Y 3 is N,

wherein Ar 1 represents a substituted or unsubstituted biphenyldiyl group,

wherein Ar 2 represents a substituted or unsubstituted biphenyldiyl group,

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 is directly bonded to the Ar 1 , and

wherein the carbazole skeleton included in the Cz 2 is directly bonded to the Ar 2 .

3. The heterocyclic compound according to claim 1 ,

wherein in the general formula (G1), the Ar 1 represents a substituted or unsubstituted biphenyl-3,3′-diyl group and the Ar 2 represents a substituted or unsubstituted biphenyl-3,3′-diyl group.

4. A heterocyclic compound represented by a general formula (G2):

wherein each of any one, two, or three of Y 1 to Y 4 in a ring A represents N, and each of the rest of Y 1 to Y 4 represents CH,

wherein in the case where each of any two or three of the Y 1 to Y 4 is N, the N of the any two or three of the Y 1 to Y 4 are not next to each other,

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 and the carbazole skeleton included in the Cz 2 are directly bonded to different phenyl groups from each other, and

wherein each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

5. A heterocyclic compound represented by a general formula (G2):

wherein each of any one or two of Y 1 to Y 4 in a ring A represents N, and each of the rest of Y 1 to Y 4 represents CH,

wherein in the case where each of two of the Y 1 to Y 4 is N, each of Y 1 and Y 3 is N,

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 and the carbazole skeleton included in the Cz 2 are directly bonded to different phenyl groups from each other, and

wherein each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

6. The heterocyclic compound according to claim 1 ,

wherein the heterocyclic compound is represented by a general formula (G3):

7. The heterocyclic compound according to claim 6 ,

wherein in the general formula (G3), the Ar 1 represents a substituted or unsubstituted biphenyl-3,3′-diyl group and the Ar 2 represents a substituted or unsubstituted biphenyl-3,3′-diyl group.

8. A heterocyclic compound represented by a general formula (G4):

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 and the carbazole skeleton included in the Cz 2 are directly bonded to different phenyl groups from each other, and

wherein each of R 1 to R 16 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

9. The heterocyclic compound according to claim 1 ,

wherein the heterocyclic compound is represented by a general formula (G5):

10. The heterocyclic compound according to claim 9 ,

wherein in the general formula (G5), the Ar 1 represents a substituted or unsubstituted biphenyl-3,3′-diyl group and the Ar 2 represents a substituted or unsubstituted biphenyl-3,3′-diyl group.

11. A heterocyclic compound represented by a general formula (G6):

wherein Cz 1 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein Cz 2 represents a substituted or unsubstituted heterocyclic group including a carbazole skeleton,

wherein the carbazole skeleton included in the Cz 1 and the carbazole skeleton included in the Cz 2 are directly bonded to different phenyl groups from each other, and

wherein each of R 1 to R 16 independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

12. The heterocyclic compound according to claim 1 ,

wherein in the general formula (G1), N in the carbazole skeleton included in the Cz 1 is directly bonded to the Ar 1 , and N in the carbazole skeleton included in the Cz 2 is directly bonded to the Ar 2 .

13. The heterocyclic compound according to claim 1 ,

wherein in the general formula (G1), the Cz 1 represents a substituted or unsubstituted carbazolyl group and the Cz 2 represents a substituted or unsubstituted carbazolyl group.

14. The heterocyclic compound according to claim 13 ,

wherein at least one of the carbazolyl groups is a N-carbazolyl group.

15. The heterocyclic compound according to claim 1 ,

wherein at least one of the heterocyclic groups is represented by a general formula (α):

wherein each of R 41 to R 48 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, a sulfanyl group, an arylamino group having 6 to 12 carbon atoms, a vinyl group, and an aryl group having 6 to 12 carbon atoms, and

wherein any adjacent substituents among the R 41 to R 48 are capable of being bonded to each other to form a ring.

16. The heterocyclic compound according to claim 1 ,

wherein at least one of the heterocyclic groups is an unsubstituted N-carbazolyl group.

17. The heterocyclic compound according to claim 1 ,

wherein the heterocyclic compound is represented by a structural formula (100):

18. The heterocyclic compound according to claim 1 ,

wherein the heterocyclic compound is represented by a structural formula (200):

19. A light-emitting element comprising the heterocyclic compound according to claim 1 .

20. A light-emitting element comprising the heterocyclic compound according to claim 1 ,

wherein the light-emitting element comprises an EL layer between a pair of electrodes, and

wherein the EL layer comprises the heterocyclic compound.

21. A light-emitting element comprising the heterocyclic compound according to claim 1 ,

wherein the light-emitting element comprises an EL layer between a pair of electrodes, the EL layer comprising a light-emitting layer, and

wherein the EL layer comprises the heterocyclic compound.

22. A light-emitting element comprising the heterocyclic compound according to claim 1 ,

wherein the light-emitting element comprises an EL layer between a pair of electrodes, the EL layer comprising a light-emitting layer,

wherein the light-emitting layer comprises three or more kinds of organic compounds, and

wherein at least one of the three or more kinds of organic compounds is the heterocyclic compound.

23. A light-emitting device comprising the light-emitting element according to claim 19 ,

wherein the light-emitting device comprises one of a transistor and a substrate.

24. An electronic device comprising the light-emitting device according to claim 23 ,

wherein the electronic device comprises one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

25. A lighting device comprising the light-emitting element according to claim 19 ,

wherein the lighting device comprises one of a transistor, a substrate and a sealing substrate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2016
From: SEO, SATOSHI; KUBOTA, YUKO; TAKAHASHI, TATSUYOSHI; MITSUMORI, SATOMI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 038266/0474 →
Priority Claims (1)
JP 2015-082469 · Apr 14, 2015 · national
Continuity (1)
Related Publication 20160308139A1 · Oct 20, 2016