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

Patent metadata

Field	Value
Publication number	US-9079879-B2
Application number	US-201113031734-A
Country	US
Kind code	B2
Filing date	Feb 22, 2011
Priority date	Mar 1, 2010
Publication date	Jul 14, 2015
Grant date	Jul 14, 2015

Abstract

An object is to provide a novel heterocyclic compound which can be used for a light-emitting element, as a host material of a light-emitting layer in which a light-emitting substance is dispersed. Other objects are to provide a light-emitting element having low driving voltage, a light-emitting element having high current efficiency, and a light-emitting element having a long lifetime. Provided are a light-emitting element including a compound in which a dibenzo[f,h]quinoxaline ring and a hole-transport skeleton are bonded through an arylene group, and a light-emitting device, an electronic device, and a lighting device each using this light-emitting element. The heterocyclic compound represented by General Formula (G1) below is provided.

First claim

What is claimed is:

1. A compound including a dibenzo[f,h]quinoxaline ring and a hole-transport skeleton which are bonded to each other through an arylene group,
wherein the hole-transport skeleton is a dibenzofuran ring or a dibenzothiophene ring.

2. The compound according to claim 1 , wherein the arylene group has one or more substituents.

3. The compound according to claim 2 , wherein the substituents are bonded to form a ring.

4. The compound according to claim 1 , wherein the arylene group is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

5. The compound according to claim 1 ,
wherein:
the compound is represented by General Formula (G1):

A represents any of a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted dibenzofuranyl group;
each of R 11 to R 19 independently represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and
Ar represents the arylene group having 6 to 13 carbon atoms.

6. The compound according to claim 5 , wherein the arylene group has one or more substituents.

7. The compound according to claim 6 , wherein the substituents are bonded to form a ring.

8. The compound according to claim 5 , wherein Ar is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

9. The compound according to claim 5 ,
wherein:
the compound is represented by General Formula (G2-1),

Z represents oxygen or sulfur; and
each of R 21 to R 27 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

10. The compound according to claim 9 , wherein the arylene group has one of more substituents.

11. The compound according to claim 10 , wherein the substituents are bonded to form a ring.

12. The compound according to claim 9 , wherein Ar is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

13. The compound according to claim 9 ,
wherein:
the compound is represented by General Formula (G3-1),

each of R 41 to R 44 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

14. The compound according to claim 13 , wherein R 42 and R 43 are bonded to R 43 and R 44 respectively to form a ring.

15. A light-emitting device comprising a light-emitting element, the light-emitting element comprising:
an electron-transport layer comprising an uncomplexed organic compound including a dibenzo[f,h]quinoxaline ring and a hole-transport skeleton which are bonded to each other through an arylene group.

16. The light-emitting device according to claim 15 , wherein the hole-transport skeleton is a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

17. The light-emitting device according to claim 15 , wherein the arylene group has one or more substituents.

18. The light-emitting device according to claim 17 , wherein the substituents are bonded to form a ring.

19. The light-emitting device according to claim 15 , wherein the arylene group is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

20. An electronic device comprising the light-emitting device according to claim 15 .

21. A lighting device comprising the light-emitting device according to claim 15 .

22. A light-emitting device comprising a light-emitting element, the light-emitting element comprising:
a light-emitting layer comprising a light-emitting material and a compound including a dibenzo[f,h]quinoxaline ring and a hole-transport skeleton which are bonded to each other through an arylene group,
wherein the compound is a host material.

23. The light-emitting device according to claim 22 , wherein the hole-transport skeleton is a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

24. The light-emitting device according to claim 22 , wherein the arylene group has one or more substituents.

25. The light-emitting device according to claim 24 , wherein the substituents are bonded to form a ring.

26. The light-emitting device according to claim 22 , wherein the arylene group is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

27. An electronic device comprising the light-emitting device according to claim 22 .

28. A lighting device comprising the light-emitting device according to claim 22 .

29. A light-emitting device comprising a light-emitting element, the light-emitting element comprising:
a light-emitting layer comprising a light-emitting material and a first compound, the first compound being a host material; and
an electron-transport layer over the light-emitting layer, the electron-transport layer comprising a second compound,
wherein each of the first compound and the second compound includes a dibenzo[f,h]quinoxaline ring and a hole-transport skeleton which are bonded to each other through an arylene group.

30. The light-emitting device according to claim 29 , wherein the hole-transport skeleton is a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

31. The light-emitting device according to claim 29 , wherein the arylene group has one or more substituents.

32. The light-emitting device according to claim 31 , wherein the substituents are bonded to form a ring.

33. The light-emitting device according to claim 29 , wherein the arylene group is any of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, and a substituted or unsubstituted m-phenylene group.

34. An electronic device comprising the light-emitting device according to claim 29 .

35. A lighting device comprising the light-emitting device according to claim 29 .

36. The compound according to claim 5 , wherein the compound is represented by any one of structural formulae (100), (101), (106), (107), (109), (116), (142), (201), and (515),

Assignees

• Kadoma Hiroshi
• Ohsawa Nobuharu
• Seo Satoshi
• Semiconductor Energy Lab

Inventors

• Kadoma Hiroshi
• Ohsawa Nobuharu
• Seo Satoshi

Classifications

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title