IP Library › Granted Patent US 10,636,976
Granted Patent B2
US 10,636,976 · App. 15/440,270 · Granted Apr 28, 2020

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

Inventors: Satoshi Seo (Kanagawa, JP); Tsunenori Suzuki (Kanagawa, JP); Tomohiro Kubota (Kanagawa, JP); Naoaki Hashimoto (Kanagawa, JP); Yusuke Takita (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0052C07D209/80C07D209/86C09K11/06H01L51/0072C09K2211/1007C09K2211/1011C09K2211/1029
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Quick Facts
Patent No.
US 10,636,976
App. No.
15/440,270
Granted
Apr 28, 2020
Kind
B2
Abstract

A novel compound in which a delayed fluorescence component due to TTA accounts for a high proportion of emissive components is provided. The organic compound includes an anthracene skeleton, an arylene group, and a substituted or unsubstituted heterocyclic group including a carbazole skeleton. The anthracene skeleton and the substituted or unsubstituted heterocyclic group including the carbazole skeleton are bonded to each other through the arylene group. The anthracene skeleton includes an aryl group at the 2-position or the 3-position.

Claims (101)

1. An organic compound represented by a general formula (G1):

wherein Ar 1 and Ar 3 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,

wherein Ar 2 represents a substituted or unsubstituted arylene group having 6 to 14 carbon atoms,

wherein Cz represents a substituted or unsubstituted heterocyclic group comprising a carbazole skeleton directly bonded to the Ar 2 , and includes an aromatic ring fused to the carbazole skeleton, and

wherein R 1 to R 7 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

2. The organic compound according to claim 1 , wherein the Ar 2 represents a substituted or unsubstituted phenylene group.

3. A light-emitting element comprising the organic compound according to claim 1 .

4. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises the organic compound according to claim 1 .

5. A light-emitting element 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 organic compound according to claim 1 .

6. A light-emitting device comprising:

the light-emitting element according to claim 3 ; and

at least one of a transistor and a substrate.

7. An electronic device comprising:

the light-emitting device according to claim 6 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

8. A lighting device comprising:

the light-emitting element according to claim 3 ; and

at least one of a housing, a sealing substrate with unevenness, and a diffusion plate.

9. An organic compound represented by a general formula (G2):

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,

wherein Ar 2 represents a substituted or unsubstituted arylene group having 6 to 14 carbon atoms,

wherein Cz represents a substituted or unsubstituted heterocyclic group comprising a carbazole skeleton directly bonded to the Ar 2 , and includes an aromatic ring fused to the carbazole skeleton,

wherein R 1 to R 7 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and

wherein R 8 to R 12 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

10. The organic compound according to claim 9 , wherein any adjacent substituents among the R 8 to the R 12 are bonded to each other to form a ring.

11. The organic compound according to claim 9 , wherein the Ar 2 represents a substituted or unsubstituted phenylene group.

12. A light-emitting element comprising the organic compound according to claim 9 .

13. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises the organic compound according to claim 9 .

14. A light-emitting element 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 organic compound according to claim 9 .

15. A light-emitting device comprising:

the light-emitting element according to claim 12 ; and

at least one of a transistor and a substrate.

16. An electronic device comprising:

the light-emitting device according to claim 15 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

17. A lighting device comprising:

the light-emitting element according to claim 12 ; and

at least one of a housing, a sealing substrate with unevenness, and a diffusion plate.

18. An organic compound represented by a general formula (G3):

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,

wherein Cz represents a substituted or unsubstituted heterocyclic group comprising a carbazole skeleton, and includes an aromatic ring fused to the carbazole skeleton,

wherein R 1 to R 7 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and

wherein R 8 to R 16 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

19. The organic compound according to claim 18 , wherein any adjacent substituents among the R 8 to the R 16 are bonded to each other to form a ring.

20. A light-emitting element comprising the organic compound according to claim 18 .

21. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises the organic compound according to claim 18 .

22. A light-emitting element 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 organic compound according to claim 18 .

23. A light-emitting device comprising:

the light-emitting element according to claim 20 ; and

at least one of a transistor and a substrate.

24. An electronic device comprising:

the light-emitting device according to claim 23 ; and

at least 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 20 ; and

at least one of a housing, a sealing substrate with unevenness, and a diffusion plate.

26. An organic compound represented by a general formula (G5):

wherein Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,

wherein R 1 to R 7 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and

wherein R 8 to R 16 each independently represent any 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, a substituted or unsubstituted arylamino group having 6 to 12 carbon atoms, a vinyl group, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

27. The organic compound according to claim 26 , wherein any adjacent substituents among the R 8 to the R 16 are bonded to each other to form a ring.

28. A light-emitting element comprising the organic compound according to claim 26 .

29. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises the organic compound according to claim 26 .

30. A light-emitting element 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 organic compound according to claim 26 .

31. A light-emitting device comprising:

the light-emitting element according to claim 28 ; and

at least one of a transistor and a substrate.

32. An electronic device comprising:

the light-emitting device according to claim 31 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

33. A lighting device comprising:

the light-emitting element according to claim 28 ; and

at least one of a housing, a sealing substrate with unevenness, and a diffusion plate.

34. An organic compound represented by a structural formula (200):

35. A light-emitting element comprising the organic compound according to claim 34 .

36. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises the organic compound according to claim 34 .

37. A light-emitting element 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 organic compound according to claim 34 .

38. A light-emitting device comprising:

the light-emitting element according to claim 37 ; and

at least one of a transistor and a substrate.

39. An electronic device comprising:

the light-emitting device according to claim 38 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

40. A lighting device comprising:

the light-emitting element according to claim 37 ; and

at least one of a housing, a sealing substrate with unevenness, and a diffusion plate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2017
From: SEO, SATOSHI; SUZUKI, TSUNENORI; KUBOTA, TOMOHIRO; HASHIMOTO, NAOAKI; TAKITA, YUSUKE
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 041427/0335 →
Priority Claims (1)
JP 2016-035629 · Feb 26, 2016 · national
Continuity (1)
Related Publication 20170250346A1 · Aug 31, 2017
Cited By (1)
US 12,557,467