IP Library Granted Patent US 10,207,992
Granted Patent B2
US 10,207,992 · App. 15/334,929 · Granted Feb 19, 2019

Dibenzocarbazole compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device

Inventors: Hiroki Suzuki (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Tsunenori Suzuki (Kanagawa, JP); Naoaki Hashimoto (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
C07D209/80C09K11/02C09K11/06H01L51/0052H01L51/0072H05B33/14H05B33/20C09K2211/1007C09K2211/1011C09K2211/1014H01L51/5016Y02P20/582
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Quick Facts
Patent No.
US 10,207,992
App. No.
15/334,929
Granted
Feb 19, 2019
Kind
B2
Abstract

A novel dibenzocarbazole compound with which a light-emitting element having low power consumption, high reliability, and high color purity can be fabricated is provided. In the dibenzocarbazole compound, an aryl group which has 14 to 30 carbon atoms and at least an anthracene skeleton is bonded to nitrogen of a dibenzo[a,g]carbazole skeleton or a dibenzo[a,i]carbazole skeleton. Furthermore, a light-emitting element including the dibenzocarbazole compound is provided.

Claims (58)

1. A dibenzocarbazole compound,

wherein an aryl group is bonded to a dibenzo[a,g]carbazole skeleton or a dibenzo[a,i] carbazole skeleton,

wherein the aryl group is an aryl group which has 14 to 30 carbon atoms and at least an anthracene skeleton, and

wherein the aryl group is bonded to a 7-position of the dibenzo[a,g]carbazole skeleton or a 11-position of the dibenzo[a,i]carbazole skeleton.

2. The dibenzocarbazole compound according to claim 1 ,

wherein the 7-position of the dibenzo[a,g]carbazole skeleton or the 11-position of the dibenzo[a,i]carbazole skeleton is bonded to the anthracene skeleton through a phenylene group.

3. The dibenzocarbazole compound according to claim 2 ,

wherein the 7-position of the dibenzo[a,g]carbazole skeleton or the 11-position of the dibenzo[a,i]carbazole skeleton is bonded to a 9-position of the anthracene skeleton through the phenylene group.

4. The dibenzocarbazole compound according to claim 1 ,

wherein the 7-position of the dibenzo[a,g]carbazole skeleton or the 11-position of the dibenzo[a,i]carbazole skeleton is bonded to a substituted or unsubstituted anthryl phenyl group having 20 to 30 carbon atoms.

5. The dibenzocarbazole compound according to claim 1 ,

wherein the 7-position of the dibenzo[a,g]carbazole skeleton or the 11-position of the dibenzo[a,i]carbazole skeleton is bonded to a substituted or unsubstituted (9-anthryl) phenyl group having 20 to 30 carbon atoms.

6. A dibenzocarbazole compound represented by General Formula (G1):

wherein R 11 to R 22 each independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and Ar represents a substituted or unsubstituted aryl group which has 14 to 30 carbon atoms and at least an anthracene skeleton.

7. The dibenzocarbazole compound represented by General Formula (G1) according to claim 6 , wherein the dibenzocarbazole compound is represented by General Formula (G2):

wherein X represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; and Y represents a substituted or unsubstituted anthryl group.

8. The dibenzocarbazole compound according to claim 7 ,

wherein the total number of carbon atoms of X and Y is 20 to 30.

9. The dibenzocarbazole compound according to claim 7 ,

wherein X represents a substituted or unsubstituted phenylene group.

10. The dibenzocarbazole compound represented by General Formula (G1) according to claim 6 , wherein the dibenzocarbazole compound is represented by General Formula (G3):

wherein R 1 to R 8 each independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms; R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

11. The dibenzocarbazole compound according to claim 10 ,

wherein the total number of carbon atoms of R 1 to R 9 and X is 6 to 16.

12. The dibenzocarbazole compound according to claim 10 ,

wherein X represents a substituted or unsubstituted phenylene group.

13. The dibenzocarbazole compound represented by General Formula (G1) according to claim 6 , wherein the dibenzocarbazole compound is represented by General Formula (G4):

wherein R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted phenylene group.

14. The dibenzocarbazole compound according to claim 13 ,

wherein the total number of carbon atoms of R 9 and X is 6 to 16.

15. The dibenzocarbazole compound represented by General Formula (G1) according to claim 6 , wherein the dibenzocarbazole compound is represented by General Formula (G5):

wherein R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted phenylene group.

16. The dibenzocarbazole compound according to claim 15 ,

wherein the total number of carbon atoms of R 9 and X is 6 to 16.

17. The dibenzocarbazole compound represented by General Formula (G1) according to claim 6 , wherein the dibenzocarbazole compound is represented by Structural Formula (100):

18. A dibenzocarbazole compound represented by General Formula (G6):

wherein R 31 to R 42 each independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and Ar represents a substituted or unsubstituted aryl group which has 14 to 30 carbon atoms and at least an anthracene skeleton.

19. The dibenzocarbazole compound represented by General Formula (G6) according to claim 18 , wherein the dibenzocarbazole compound is represented by General Formula (G7):

wherein X represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; and Y represents a substituted or unsubstituted anthryl group.

20. The dibenzocarbazole compound according to claim 19 ,

wherein the total number of carbon atoms of X and Y is 20 to 30.

21. The dibenzocarbazole compound according to claim 19 ,

wherein X represents a substituted or unsubstituted phenylene group.

22. The dibenzocarbazole compound represented by General Formula (G6) according to claim 18 , wherein the dibenzocarbazole compound is represented by General Formula (G8):

wherein R 1 to R 8 each independently represent hydrogen or an alkyl group having 1 to 4 carbon atoms; R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

23. The dibenzocarbazole compound according to claim 22 ,

wherein the total number of carbon atoms of R 1 to R 9 and X is 6 to 16.

24. The dibenzocarbazole compound according to claim 22 ,

wherein X represents a substituted or unsubstituted phenylene group.

25. The dibenzocarbazole compound represented by General Formula (G6) according to claim 18 , wherein the dibenzocarbazole compound is represented by General Formula (G9):

wherein R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted phenylene group.

26. The dibenzocarbazole compound according to claim 25 ,

wherein the total number of carbon atoms of R 9 and X is 6 to 16.

27. The dibenzocarbazole compound represented by General Formula (G6) according to claim 18 , wherein the dibenzocarbazole compound is represented by General Formula (G10):

wherein R 9 represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and X represents a substituted or unsubstituted phenylene group.

28. The dibenzocarbazole compound according to claim 27 ,

wherein the total number of carbon atoms of R 9 and X is 6 to 16.

29. The dibenzocarbazole compound represented by General Formula (G6) according to claim 18 , wherein the dibenzocarbazole compound is represented by Structural Formula (136):

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2016
From: SUZUKI, HIROKI; SEO, SATOSHI; SUZUKI, TSUNENORI; HASHIMOTO, NAOAKI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 040141/0231 →
Priority Claims (1)
JP 2015-214392 · Oct 30, 2015 · national
Continuity (1)
Related Publication 20170125703A1 · May 4, 2017
Cited By (2)
US 12,388,086 US 12,534,434