IP Library › Granted Patent US 7,842,945
Granted Patent B2
US 7,842,945 · App. 11/789,407 · Granted Nov 30, 2010

Anthracene derivative, and light-emitting element, light-emitting device, electronic device using anthracene derivative

Assignee: Semiconductor Energy Laboratory Co., Ltd.
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Quick Facts
Patent No.
US 7,842,945
App. No.
11/789,407
Granted
Nov 30, 2010
Kind
B2
Abstract

An object is to provide a novel anthracene derivative. Another object is to provide a light-emitting element with high luminous efficiency. Yet another object is to provide a light-emitting element with a long lifetime. Still another object is to provide a light-emitting device and an electronic device having a long lifetime by using the light-emitting elements of the present invention. The anthracene derivative represented by General Formula (1) is provided. The ability of the anthracene derivative represented by General Formula (1) to exhibit high luminous efficiency allows the production of a light-emitting element with high luminous efficiency and a long lifetime.

Claims (176)

1. An anthracene derivative represented by the structure:

wherein Ar 1 and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, and

wherein A is selected from:

Ar 11 to Ar 13 each represent an aryl group having 6 to 25 carbon atoms;

α represents an arylene group having 6 to 25 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

β represents an arylene group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

2. An anthracene derivative according to claim 1 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 11 to R 24 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 33 to R 37 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms; and

R 43 to R 46 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

3. An anthracene derivative according to claim 1 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 25 and R 26 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

4. An anthracene derivative according to claim 1 ,

wherein A is selected from:

Ar 11 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 25 and R 26 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents any of a phenyl group, 1-naphthyl group, and 2-naphthyl group; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

5. An anthracene derivative according to claim 1 ,

wherein Ar 1 and Ar 2 each are a substituent represented by the structure:

R 1 to R 5 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

6. An anthracene derivative according to claim 1 ,

wherein Ar 1 and Ar 2 are independently selected from:

R 6 and R 7 each represent any of an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

7. An anthracene derivative represented by the structure:

wherein Ar 1 and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, and

wherein A is selected from:

Ar 11 to Ar 13 each represent an aryl group having 6 to 25 carbon atoms;

α represents an arylene group having 6 to 25 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

β represents an arylene group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

8. An anthracene derivative according to claim 7 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 11 to R 24 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 33 to R 37 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms; and

R 43 to R 46 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

9. An anthracene derivative according to claim 7 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 25 and R 26 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

10. An anthracene derivative according to claim 7 ,

wherein A is selected from:

Ar 11 represents any of a phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 25 and R 26 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

11. An anthracene derivative according to claim 7 ,

wherein Ar 1 and Ar 2 each are a substituent represented by the structure:

R 1 to R 5 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

12. An anthracene derivative according to claim 7 ,

wherein Ar 1 and Ar 2 are independently selected from:

R 6 and R 7 each represent any of an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

13. A light-emitting device comprising a light-emitting element which comprises an anthracene derivative between a pair of electrodes,

wherein the anthracene derivative is represented by the structure:

wherein Ar 1 and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, and

wherein A is selected from:

Ar 11 to Ar 13 each represent an aryl group having 6 to 25 carbon atoms;

α represents an arylene group having 6 to 25 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

β represents an arylene group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

14. A light-emitting device according to claim 13 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 11 to R 24 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 33 to R 37 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms; and

R 43 to R 46 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

15. A light-emitting device according to claim 13 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 25 and R 26 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

16. A light-emitting device according to claim 13 ,

wherein A is selected from:

Ar 11 represents any of a phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 25 and R 26 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

17. A light-emitting device according to claim 13 ,

wherein Ar 1 and Ar 2 each are a substituent represented by the structure:

R 1 to R 5 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

18. A light-emitting device according to claim 13 ,

wherein Ar 1 and Ar 2 are independently selected from:

R 6 and R 7 each represent any of an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

19. A light-emitting device comprising a light-emitting element which comprises an anthracene derivative between a pair of electrodes,

wherein the anthracene derivative is represented by the structure:

wherein Ar 1 and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, and

wherein A is selected from:

Ar 11 to Ar 13 each represent an aryl group having 6 to 25 carbon atoms;

α represents an arylene group having 6 to 25 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

β represents an arylene group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

20. A light-emitting device according to claim 19 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 11 to R 24 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

R 33 to R 37 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms;

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms; and

R 43 to R 46 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

21. A light-emitting device according to claim 19 ,

wherein A is selected from:

Ar 11 represents an aryl group having 6 to 25 carbon atoms;

R 25 and R 26 each represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents an aryl group having 6 to 25 carbon atoms;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents an aryl group having 6 to 25 carbon atoms; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

22. A light-emitting device according to claim 19 ,

wherein A is selected from:

Ar 11 represents any of a phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 25 and R 26 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms;

Ar 21 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group;

R 31 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms;

Ar 31 represents any of phenyl group, 1-naphthyl group, and 2-naphthyl group; and

R 41 and R 42 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms.

23. A light-emitting device according to claim 19 ,

wherein Ar 1 and Ar 2 each are a substituent represented by the structure:

R 1 to R 5 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

24. A light-emitting device according to claim 19 ,

wherein Ar 1 and Ar 2 are independently selected from:

R 6 and R 7 each represent any of an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 15 carbon atoms.

25. An electronic device comprising a display portion which comprises a light-emitting device according to claim 13 .

26. An electronic device comprising a display portion which comprises a light-emitting device according to claim 19 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2007
From: EGAWA, MASAKAZU; NAKASHIMA, HARUE; KAWAKAMI, SACHIKO; SUZUKI, TSUNENORI; NOMURA, RYOJI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 019657/0489 →
Priority Claims (2)
JP 2006-127118 · Apr 28, 2006 · national
JP 2006-233244 · Aug 30, 2006 · national
Continuity (1)
Related Publication 20080017853A1 · Jan 24, 2008