IP Library Granted Patent US 9,056,883
Granted Patent B2
US 9,056,883 · App. 13/079,936 · Granted Jun 16, 2015

Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Hideko Inoue (Kanagawa, JP); Tomoka Nakagawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
C07F15/0033H01L51/0085H01L51/5016H01L51/0087C07F15/0086C09K2211/1044C09K11/06C09K2211/185
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Quick Facts
Patent No.
US 9,056,883
App. No.
13/079,936
Granted
Jun 16, 2015
Kind
B2
Abstract

An object is to provide a novel organometallic complex capable of emitting phosphorescence by using, as a ligand, an organic compound with which a variety of derivatives can be easily synthesized. Another object is to provide an organometallic complex having high heat resistance. Other objects are to provide a light-emitting element having high emission efficiency and to provide a light-emitting device, an electronic device, and a lighting device having reduced power consumption. Provided are an organometallic complex including a structure represented by the following General Formula (G1), and a light-emitting element, a light-emitting device, an electronic device, and a lighting device formed using the organometallic complex including the structure represented by the following General Formula (G1).

Claims (64)

1. A complex including a structure represented by Formula (G1),

wherein:

R 1 represents any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms;

Ar 1 represents a condensed aromatic hydrocarbon group having 10 to 13 carbon atoms, and Ar 2 represents an aromatic hydrocarbon group having 6 to 13 carbon atoms; and

M represents a Group 9 element or a Group 10 element.

2. The complex according to claim 1 , wherein R 3 is hydrogen.

3. The complex according to claim 1 , wherein M is iridium or platinum.

4. A light-emitting element comprising the complex according to claim 1 .

5. The light-emitting element according to claim 4 , further comprising a light-emitting layer,

wherein the complex is included in the light-emitting layer.

6. A light-emitting device comprising the light-emitting element according to claim 4 .

7. An electronic device comprising the light-emitting device according to claim 6 .

8. A lighting device comprising the light-emitting device according to claim 6 .

9. The complex according to claim 1 , wherein Ar 1 has a substituent.

10. The complex according to claim 1 , wherein Ar 2 has a substituent.

11. A complex represented by Formula (G3),

wherein:

R 1 represents any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms;

one of Ar 1 and Ar 2 represents a condensed aromatic hydrocarbon group having 10 to 13 carbon atoms, and the other of Ar 1 and Ar 2 represents an aromatic hydrocarbon group having 6 to 13 carbon atoms;

M represents a Group 9 element or a Group 10 element;

L represents a monoanionic bidentate chelate ligand having a beta-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, and a monoanionic bidentate chelate ligand in which each of two ligands is nitrogen; and

n is 2 when M is a Group 9 element or n is 1 when M is a Group 10 element.

12. The complex according to claim 11 , wherein R 3 is hydrogen.

13. The complex according to claim 11 , wherein M is iridium or platinum.

14. A light-emitting element comprising the complex according to claim 11 .

15. The light-emitting element according to claim 14 , further comprising a light-emitting layer,

wherein the complex is included in the light-emitting layer.

16. A light-emitting device comprising the light-emitting element according to claim 14 .

17. An electronic device comprising the light-emitting device according to claim 16 .

18. A lighting device comprising the light-emitting device according to claim 16 .

19. The complex according to claim 11 , wherein Ar 1 has a substituent.

20. The complex according to claim 11 , wherein Ar 2 has a substituent.

21. The complex according to claim 11 , wherein L is represented by any of Formulae (L1) to (L6),

wherein:

R 10 to R 29 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen, a haloalkyl group, an alkoxy group having 1 to 4 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms;

A 1 to A 3 separately represent nitrogen, carbon bonded to hydrogen, or carbon bonded to a substituent R; and

the substituent R represents any of an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.

22. A complex represented by Formula (G5),

wherein:

R 1 represents any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms;

R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms;

Ar 1 represents a condensed aromatic hydrocarbon group having 10 to 13 carbon atoms, and Ar 2 represents an aromatic hydrocarbon group having 6 to 13 carbon atoms;

M represents a Group 9 element or a Group 10 element; and

n is 2 when M is a Group 9 element or n is 1 when M is a Group 10 element.

23. The complex according to claim 22 , wherein R 3 is hydrogen.

24. The complex according to claim 22 , wherein M is iridium or platinum.

25. A light-emitting element comprising the complex according to claim 22 .

26. The light-emitting element according to claim 25 , further comprising a light-emitting layer,

wherein the complex is included in the light-emitting layer.

27. A light-emitting device comprising the light-emitting element according to claim 25 .

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

29. A lighting device comprising the light-emitting device according to claim 27 .

30. The complex according to claim 22 , wherein Ar 1 has a substituent.

31. The complex according to claim 22 , wherein Ar 2 has a substituent.

32. The complex according to claim 11 ,

wherein Ar 1 represents a benzene ring.

33. The complex according to claim 1 ,

wherein Ar 1 represents a naphthalene ring or a fluorene ring; and

wherein Ar 2 represents an aromatic hydrocarbon group having 6 to 13 carbon atoms.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2011
From: INOUE, HIDEKO; NAKAGAWA, TOMOKA; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 026075/0504 →
Priority Claims (1)
JP 2010-087626 · Apr 6, 2010 · national
Continuity (1)
Related Publication 20110245495A1 · Oct 6, 2011