Carbazole Compound, Material for Light-Emitting Element, Organic Semiconductor Material, Light-Emitting Element

• US 20120091887A1
• Filed: 10/12/2011
• Published: 04/19/2012
• Est. Priority Date: 10/15/2010
• Status: Active Grant

• Current Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Original Assignee: Semiconductor Energy Laboratory Co., Ltd.
• Inventors: Osaka, Harue, Shitagaki, Satoko, Nowatari, Hiromi, Ohsawa, Nobuharu
• Granted Patent: US 9,133,173 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/19 Tandem OLEDs
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

To provide a novel carbazole compound that has an excellent carrier-transport property and can be used for a transport layer or as a host material in a light-emitting element. Further, to provide an organic semiconductor material and a material for a light-emitting element using the carbazole compound. A carbazole compound in which the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is substituted with the 2- or 3-position of a carbazole skeleton directly or via an arylene group can be synthesized. The carbazole compound is found to have a suitable carrier-transport property, a good film quality, and be used suitably as a material of a light-emitting element and an organic semicondcutor material. Note that nitrogen of the carbazole skeleton is substituted with any of a phenyl group, a biphenyl group, and a naphthyl group.

Claims

1. A carbazole compound represented by a general formula (G1),

2. The carbazole compound according to claim 1, represented by the general formula (G1),

wherein:

Ar³ is a substituent represented by the general formula (g2) or a substituent represented by the general formula (g3);

when Ar² is bonded at the α

position, Ar³ is bonded at the γ

position;

or

when Ar² is bonded at the β

position, Ar³ is bonded at the δ

position.

9. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein the groups, a¹, a², and a³, are independently any of groups represented by structural formulae (a-1) to (a-7).

10. The carbazole compound according to any one of claims 1, 3, 5, and 7;

wherein the groups, R¹ to R¹⁵, are independently any of groups represented by structural formulae (R-1) to (R-13).

11. The carbazole compound according to any one of claims 1, 3, 5, and 7;

wherein the group, Ar⁴, is any of groups represented by structural formulae (Ar-1) to (Ar-6).

12. The carbazole compound according to any one of claims 1, 3, 5, and 7;

wherein the group, Ar¹, is any of groups represented by the following structural formulae (Ar-1) to (Ar-6).

13. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein n is 0.

14. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein the group represented by Ar¹ is a phenyl group.

15. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein Q¹ and Q² represent sulfur.

16. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein m and k are both 0.

19. The carbazole compound according to any one of claims 1, 3, 5, and 7, wherein Ar³ is hydrogen and k is 1.

22. A material for a light-emitting element including the carbazole compound according to any one of claims 1, 3, 5, 7, 17-18, and 20-21.

23. An organic semiconductor material including the carbazole compound according to any one of claims 1, 3, 5, 7, 17-18, and 20-21.

3. A carbazole compound represented by a general formula (G1),

4. The carbazole compound according to claim 3, represented by the general formula (G1),

wherein:

Ar³ is a substituent represented by the general formula (g3) or a substituent represented by the general formula (g5);

when Ar² is bonded at the α

position, Ar³ is bonded at the γ

position;

or

when Ar² is bonded at the β

position, Ar³ is bonded at the δ

position.

5. A carbazole compound represented by a general formula (G1)

6. The carbazole compound according to claim 5, represented by the general formula (G1),

wherein:

Ar³ is a substituent represented by the general formula (g5);

when Ar² is bonded at the α

position, Ar³ is bonded at the γ

position;

or

when Ar² is bonded at the β

position, Ar³ is bonded at the δ

position.

7. A carbazole compound represented by a general formula (G1),

8. The carbazole compound according to claim 7, represented by the general formula (G1),

wherein:

Ar³ is a substituent represented by the general formula (g7);

when Ar² is bonded at the α

position, Ar³ is bonded at the γ

position;

or

when Ar² is bonded at the β

position, Ar³ is bonded at the δ

position.

17. A carbazole compound represented by a structural formula (150).

18. A carbazole compound represented by a structural formula (154)

20. A carbazole compound represented by a structural formula (172).

21. A carbazole compound represented by a structural formula (160).

24. A light-emitting element including a carbazole compound represented by a general formula (G1), wherein a layer containing an organic compound is interposed between a pair of electrodes,

28. The light-emitting element in which the layer containing the organic compound includes the carbazole compound represented by the general formula (G1), according to any one of claims 24 to 27,

wherein:

when Ar³ is a substituent other than hydrogen, Ar² is bonded at the position α and

Ar³ is bodned at the position γ

, or the Ar² is bodned at the position β and

Ar³ is bodned at the position δ

.

29. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27,

wherein the groups, a¹, a², and a³, are independently any of groups represented by structural formulae (a-1) to (a-7).

30. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27,

wherein the groups, R¹ to R¹⁵, are independently any of groups represented by structural formulae (R-1) to (R-13).

31. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27,

wherein the group, Ar⁴, is any of groups represented by structural formulae (Ar-1) to (Ar-6).

32. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27,

wherein the group, Ar¹ is any of groups represented by the structural formulae (Ar-1) to (Ar-6).

33. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27, wherein n is 0.

34. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27, wherein the group, Ar¹, is a phenyl group.

35. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27, wherein Q¹ and Q² are the same element.

36. The light-emitting element in which the layer containing the organic compound includes the carbazole compound, according to any one of claims 24 to 27, wherein Ar³ is hydrogen and k is 1.

37. The light-emitting element according to any one of claims 24 to 27, wherein the layer containing the organic compound includes a carbazole compound represented by a structural formula (172).

38. The light-emitting element according to any one of claims 24 to 27, wherein the layer containing the organic compound includes a carbazole compound represented by a structural formula (160).

25. A light-emitting element including a carbazole compound represented by a general formula (G1), wherein a layer containing an organic compound is interposed between a pair of electrodes,

26. A light-emitting element including a carbazole compound represented by a general formula (G1), wherein a layer containing an organic compound is interposed between a pair of electrodes,

27. A light-emitting element including a carbazole compound represented by a general formula (G1), wherein a layer containing an organic compound is interposed between a pair of electrodes,