IP Library › Granted Patent US 8,288,012
Granted Patent B2
US 8,288,012 · App. 11/962,509 · Granted Oct 16, 2012

Anthracene derivatives and light-emitting devices using the anthracene derivatives

Assignee: Semiconductor Energy Laboratory Co., Ltd.
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Quick Facts
Patent No.
US 8,288,012
App. No.
11/962,509
Granted
Oct 16, 2012
Kind
B2
Abstract

The present invention provides novel anthracene derivatives. In particular, the present invention provides light-emitting elements with high luminous efficiency, and light-emitting elements with long lifetime. Further, the present invention provides light-emitting devices and electronic devices having long lifetime by using these light-emitting elements. An anthracene derivative represented by the general formula (1) is provided. In addition, since the anthracene derivative represented by the general formula (1) has high luminous efficiency, a light-emitting element using the anthracene derivative represented by the general formula (1) can also have high luminous efficiency. By using the anthracene derivative represented by the general formula (1), light-emitting elements with long lifetime can be provided.

Claims (169)

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, Ar 3 represents an arylene 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 33 to R 37 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms; and

R 43 to R 46 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloallcyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

4. An anthracene derivative according to claim 1 ,

wherein A is selected from:

Ar 11 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

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

Ar 21 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms;

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

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

5. An anthracene derivative according to claim 1 ,

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

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

6. An anthracene derivative according to claim 1 , wherein Ar 3 is selected from:

wherein R 51 to R 62 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

7. An anthracene derivative represented by the structure:

wherein Ar l and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, Ar 3 represents an arylene 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloallcyl group having 1 to 4 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon toms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 33 to R 37 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon toms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloallcyl group having 1 to 4 carbon atoms; and

R 43 to R 46 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

10. An anthracene derivative according to claim 7 ,

wherein A is selected from:

Ar 11 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

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

Ar 21 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms;

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

Ar 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.

11. An anthracene derivative according to claim 7 ,

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

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

12. An anthracene derivative according to claim 7 , wherein Ar 3 is selected from:

wherein R 51 to R 62 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 l and Ar 2 each represent an aryl group having 6 to 25 carbon atoms, Ar 3 represents an arylene 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 33 to R 37 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms; and

R 43 to R 46 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 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 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

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

wherein A is selected from:

Ar 11 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

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

Ar 21 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms;

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

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

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

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

R 1 to R 5 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloaayl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.

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

wherein Ar 3 is selected from:

wherein R 51 to R 62 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

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

20. 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, Ar 3 represents an arylene 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 32 represents an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, or a haloalkyl group having 1 to 4 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 a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

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

wherein A is selected from:

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

R 11 to R 24 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon toms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

R 33 to R 37 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms; and

R 43 to R 46 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

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

wherein A is selected from:

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

R 25 and R 26 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms;

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

R 41 and R 42 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

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

wherein A is selected from:

Ar 11 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

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

Ar 21 represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group;

R 31 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms;

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

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

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

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

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

25. A light-emitting device according to claim 20 , wherein Ar 3 is selected from:

wherein R 51 to R 62 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogen atom, or a haloalkyl group having 1 to 4 carbon atoms.

26. An electronic device comprising a display portion which comprises a light-emitting device according to claim 20 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2007
From: NOMURA, HIROKO; KAWAKAMI, SACHIKO; OHSAWA, NOBUHARU; SUZUKI, TSUNENORI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 020410/0974 →
Priority Claims (1)
JP 2006-355196 · Dec 28, 2006 · national
Continuity (1)
Related Publication 20090004506A1 · Jan 1, 2009