IP Library › Granted Patent US 8,399,665
Granted Patent B2
US 8,399,665 · App. 12/898,377 · Granted Mar 19, 2013

Organometallic complex, and light-emitting element, light-emitting device, electronic device and electronic device using the organometallic complex

Inventors: Hideko Inoue (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
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Quick Facts
Patent No.
US 8,399,665
App. No.
12/898,377
Granted
Mar 19, 2013
Kind
B2
Abstract

An object is to provide a novel organometallic complex capable of emitting phosphorescence, an organometallic complex which exhibits deep red emission, and a light-emitting element which provides deep red emission. Provided is an organometallic complex having a structure represented by the following General Formula (G1). In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 represent substituents, and M is a central metal and represents either a Group 9 element or a Group 10 element.

Claims (87)

1. An organometallic complex comprising a structure represented by General Formula (G1):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

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

R 4 , R 5 ,R 6 ,R 7 , R 8 , and R 9 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms; and

M is a central metal and represents either a Group 9 element or a Group 10 element.

2. An organometallic complex comprising a structure represented by General Formula (G2):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 4 , R 5 , R 6 , R 7 , and R 8 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms; and

M is a central metal and represents either a Group 9 element or a Group 10 element.

3. An organometallic complex comprising a structure represented by General Formula (G3):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 5 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms; and

M is a central metal and represents either a Group 9 element or a Group 10 element.

4. An organometallic complex represented by General Formula (G4):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

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

R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element;

L represents a monoanionic ligand; and

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

5. An organometallic complex represented by General Formula (G5):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 4 , R 5 , R 6 , R 7 , and R 8 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element;

L represents a monoanionic ligand;

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

6. An organometallic complex represented by General Formula (G6):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 5 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element;

L represents a monoanionic ligand;

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

7. The organometallic complex according to claim 4 ,

wherein the monoanionic ligand is any of 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 two ligand elements are both nitrogen.

8. The organometallic complex according to claim 5 ,

wherein the monoanionic ligand is any of 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 two ligand elements are both nitrogen.

9. The organometallic complex according to claim 6 ,

wherein the monoanionic ligand is any of 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 two ligand elements are both nitrogen.

10. The organometallic complex according to claim 4 , wherein the monoanionic ligand is represented by any of Structural Formulas (L1) to (L6)

wherein:

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

A 1 , A 2 , and A 3 individually represent nitrogen N or carbon C—R; and

R represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group having 1 to 4 carbon atoms.

11. The organometallic complex according to claim 5 , wherein the monoanionic ligand is represented by any of Structural Formulas (L1) to (L6)

wherein:

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

A 1 , A 2 , and A 3 individually represent nitrogen N or carbon C—R; and

R represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group having 1 to 4 carbon atoms.

12. The organometallic complex according to claim 6 , wherein the monoanionic ligand is represented by any of Structural Formulas (L1) to (L6)

wherein:

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

A 1 , A 2 , and A 3 individually represent nitrogen N or carbon C—R; and

R represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group having 1 to 4 carbon atoms.

13. An organometallic complex represented by General Formula (G7):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

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

R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element; and

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

14. An organometallic complex represented by General Formula (G8):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 4 , R 5 , R 6 , R 7 , and R 8 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element; and

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

15. An organometallic complex represented by General Formula (G9):

wherein:

R 1 and R 2 individually represent any of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;

R 5 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

M is a central metal and represents either a Group 9 element or a Group 10 element; and

n is 2 when the central metal is the Group 9 element or n is 1 when the central metal is the Group 10 element.

16. The organometallic complex according to claim 1 , wherein the central metal is iridium or platinum.

17. The organometallic complex according to claim 2 , wherein the central metal is iridium or platinum.

18. The organometallic complex according to claim 3 , wherein the central metal is iridium or platinum.

19. The organometallic complex according to claim 4 , wherein the central metal is iridium or platinum.

20. The organometallic complex according to claim 5 , wherein the central metal is iridium or platinum.

21. The organometallic complex according to claim 6 , wherein the central metal is iridium or platinum.

22. The organometallic complex according to claim 13 , wherein the central metal is iridium or platinum.

23. The organometallic complex according to claim 14 , wherein the central metal is iridium or platinum.

24. The organometallic complex according to claim 15 , wherein the central metal is iridium or platinum.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 5, 2010
From: INOUE, HIDEKO; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 025094/0241 →
Priority Claims (1)
JP 2009-232961 · Oct 7, 2009 · national
Continuity (1)
Related Publication 20110082296A1 · Apr 7, 2011