IP Library › Granted Patent US 8,334,061
Granted Patent B2
US 8,334,061 · App. 12/748,902 · Granted Dec 18, 2012

Heterocyclic compound, and light-emitting element, light-emitting device, lighting device, and electronic appliance using heterocyclic compound

Assignee: Semiconductor Energy Laboratory Co., Ltd.
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Quick Facts
Patent No.
US 8,334,061
App. No.
12/748,902
Granted
Dec 18, 2012
Kind
B2
Abstract

An object is to provide a novel heterocyclic compound having a bipolar property. Another object is to provide a light-emitting element, a light-emitting device, and an electronic appliance each having high emission efficiency. A heterocyclic compound represented by a general formula (G1), a light-emitting element, a light-emitting device, and an electronic appliance each formed using the heterocyclic compound represented by the general formula (G1) are provided. By use of the heterocyclic compound represented by the general formula (G1) to a light-emitting element, a light-emitting device, and an electronic appliance, the light-emitting element, the light-emitting device, and the electronic appliance can each have high emission efficiency.

Claims (114)

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

wherein:

Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, Ar 1 and an α carbon atom are bonded to each other to form a carbazole skeleton and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, or Ar 1 and Ar 2 are bonded to each other to form a carbazole skeleton;

Het represents any one of substituents represented by the following general formulae (S1-1) and (S1-2);

Ar 3 to Ar 6 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and

R 1 represents any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an an aryl group having 6 to 10 carbon atoms in a ring.

2. The heterocyclic compound according to claim 1 ,

wherein:

the heterocyclic compound is represented by a general formula (G2), and

R 11 to R 20 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

3. The heterocyclic compound according to claim 2 ,

wherein:

Het represents any one of substituents represented by the following general formulae (S2-1) and (S2-2), and

R 31 to R 50 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

4. The heterocyclic compound according to claim 2 ,

wherein:

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

5. The heterocyclic compound according to claim 2 ,

wherein:

the heterocyclic compound is represented by a general formula (G3), and

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

6. The heterocyclic compound according to claim 2 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

7. A light-emitting device comprising a light-emitting element, the light-emitting element comprising:

a pair of electrodes; and

a layer including a light-emitting substance and a heterocyclic compound between the pair of electrodes,

wherein:

the heterocyclic compound is represented by a general formula (G1);

Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, Ar 1 and an α carbon atom are bonded to each other to form a carbazole skeleton and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, or Ar 1 and Ar 2 are bonded to each other to form a carbazole skeleton;

Het represents any one of substituents represented by the following general formulae (S1-1) and (S1-2);

Ar 3 to Ar 6 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and

R 1 represents any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

8. The light-emitting device according to claim 7 , wherein the light-emitting substance is a phosphorescent compound.

9. The light-emitting device according to claim 7 ,

wherein:

the heterocyclic compound is represented by a general formula (G2), and

R 11 to R 20 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

10. The light-emitting device according to claim 9 ,

wherein:

Het represents any one of substituents represented by the following general formulae (S2-1) and (S2-2), and

R 31 to R 50 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

11. The light-emitting device according to claim 9 ,

wherein:

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

12. The light-emitting device according to claim 9 ,

wherein:

the heterocyclic compound is represented by a general formula (G3), and

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

13. The light-emitting device according to claim 9 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

14. A lighting device comprising a light-emitting element, the light-emitting element comprising:

a pair of electrodes; and

a layer including a light-emitting substance and a heterocyclic compound between the pair of electrodes,

wherein:

the heterocyclic compound is represented by a general formula (G1);

Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, Ar 1 and an α carbon atom are bonded to each other to form a carbazole skeleton and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, or Ar 1 and Ar 2 are bonded to each other to form a carbazole skeleton;

Het represents any one of substituents represented by the following general formulae (S1-1) and (S1-2);

Ar 3 to Ar 6 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and

R 1 represents any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

15. The lighting device according to claim 14 ,

wherein the light-emitting substance is a phosphorescent compound.

16. The lighting device according to claim 14 ,

wherein:

the heterocyclic compound is represented by a general formula (G2), and

R 11 to R 20 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

17. The lighting device according to claim 16 ,

wherein:

Het represents any one of substituents represented by the following general formulae (S2-1) and (S2-2), and

R 31 to R 50 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

18. The lighting device according to claim 16 ,

wherein:

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

19. The lighting device according to claim 16 ,

wherein:

the heterocyclic compound is represented by a general formula (G3), and

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

20. The lighting device according to claim 16 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

21. An electronic appliance comprising a light-emitting element, the light-emitting element comprising:

a pair of electrodes; and

a layer including a light-emitting substance and a heterocyclic compound between the pair of electrodes,

wherein:

the heterocyclic compound is represented by a general formula (G1);

Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, Ar 1 and an α carbon atom are bonded to each other to form a carbazole skeleton and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, or Ar 1 and Ar 2 are bonded to each other to form a carbazole skeleton;

Het represents any one of substituents represented by the following general formulae (S1-1) and (S1-2);

Ar 3 to Ar 6 independently represent a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring, and

R 1 represents any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

22. The electronic appliance according to claim 21 ,

wherein the light-emitting substance is a phosphorescent compound.

23. The electronic appliance according to claim 21 ,

wherein:

the heterocyclic compound is represented by general formula (G2), and

R 11 to R 20 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

24. The electronic appliance according to claim 23 ,

wherein:

Het represents any one of substituents represented by the following general formulae (S2-1) and (S2-2), and

R 31 to R 50 independently represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms in a ring.

25. The electronic appliance according to claim 23 ,

wherein:

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

26. The electronic appliance according to claim 23 ,

wherein:

the heterocyclic compound is represented by a general formula (G3), and

Het represents any one of substituents represented by the following structural formula (S3-1) and general formula (S4-1)

27. The electronic appliance according to claim 23 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

28. The heterocyclic compound according to claim 5 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

29. The light-emitting device according to claim 12 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

30. The lighting device according to claim 19 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to faun a carbazole skeleton.

31. The electronic appliance according to claim 26 ,

wherein any two of an α carbon atom, a β carbon atom, and a γ carbon atom are bonded to each other to form a carbazole skeleton.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2010
From: NOMURA, HIROKO; KADOMA, HIROSHI; KAWAKAMI, SACHIKO; OHSAWA, NOBUHARU; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 024154/0103 →
Priority Claims (1)
JP 2009-086675 · Mar 31, 2009 · national
Continuity (1)
Related Publication 20100244672A1 · Sep 30, 2010