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

Patent metadata

Field	Value
Publication number	US-9065061-B2
Application number	US-91421610-A
Country	US
Kind code	B2
Filing date	Oct 28, 2010
Priority date	Nov 2, 2009
Publication date	Jun 23, 2015
Grant date	Jun 23, 2015

Abstract

Provided are organometallic complexes that can exhibit phosphorescence. One of the novel organometallic complexes is represented by General Formula (G1). In General Formula (G1), R 1 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aralkyl group having 7 to 10 carbon atoms which may have a substituent. In addition, R 2 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent. Further, Ar represents an arylene group having 6 to 13 carbon atoms which may have a substituent. Further, M represents a Group 9 element or a Group 10 element.

First claim

The invention claimed is:

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

wherein:
R 1 represents any of a substituted or unsubstituted cycloalkyl group having 5 to 8 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms;
R 2 represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 8 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; and
M represents a Group 9 element or a Group 10 element.

2. The organometallic complex according to claim 1 ,
wherein the organometallic complex comprises a structure represented by General Formula (G3):

and
wherein:
R 3 to R 6 individually represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an arylthio group having 6 to 12 carbon atoms, an alkylamino group having 1 to 4 carbon atoms, a monoarylamino or diarylamino group having 6 to 24 carbon atoms, a cyano group, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

3. The organometallic complex according to claim 1 ,
wherein the organometallic complex comprises a structure represented by General Formula (G5):

and
wherein:
R 7 to R 10 individually represent hydrogen or an electron-withdrawing group.

4. The organometallic complex according to claim 3 , wherein the electron-withdrawing group is a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group substituted by a fluoro group, or a phenyl group substituted by a trifluoromethyl group.

5. The organometallic complex according to claim 1 ,
wherein the organometallic complex comprises a structure represented by General Formula (G7):

and
wherein:
R 11 represents a cycloalkyl group having 5 to 8 carbon atoms;
R 12 to R 16 individually represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, and a phenyl group; and
R 17 to R 20 individually represent hydrogen or an electron-withdrawing group.

6. The organometallic complex according to claim 5 , wherein the electron-withdrawing group is a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group substituted by a fluoro group, or a phenyl group substituted by a trifluoromethyl group.

7. The organometallic complex according to claim 5 , wherein each of R 12 to R 16 is hydrogen.

8. A light-emitting element comprising the organometallic complex according to claim 1 between a pair of electrodes.

9. A display device comprising a pixel portion, wherein the pixel portion comprises the light-emitting element according to claim 8 .

10. An electronic device comprising a display portion, wherein the display portion comprises the light-emitting element according to claim 8 .

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

12. A light-emitting element comprising;
a first light-emitting unit and a second light-emitting unit between a pair of electrodes,
wherein the first light-emitting unit contains the organometallic complex according to claim 1 , and
wherein the second light-emitting unit contains a light-emitting material that emits light with a longer wavelength than the organometallic complex.

13. A light-emitting element comprising;
a first light-emitting unit, a second light-emitting unit, and a third light-emitting unit between a pair of electrodes,
wherein the first light-emitting unit contains the organometallic complex according to claim 1 ,
wherein the second light-emitting unit contains a first light-emitting material that emits light with a longer wavelength than the organometallic complex, and
wherein the third light-emitting unit contains a second light-emitting material that emits light with a longer wavelength than the organometallic complex and a shorter wavelength than the first light-emitting material.

14. An organometallic complex represented by General Formula (G2):

wherein:
R 1 represents any of a substituted or unsubstituted cycloalkyl group having 5 to 8 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms;
R 2 represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 8 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms;
M represents a Group 9 element or a Group 10 element; and
n=3 when M is a Group 9 element, and n=2 when M is a Group 10 element.

15. The organometallic complex according to claim 14 ,
wherein the organometallic complex is represented by General Formula (G4):

and
wherein:
R 3 to R 6 individually represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an arylthio group having 6 to 12 carbon atoms, an alkylamino group having 1 to 4 carbon atoms, a monoarylamino or diarylamino group having 6 to 24 carbon atoms, a cyano group, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

16. The organometallic complex according to claim 14 ,
wherein the organometallic complex is represented by General Formula (G6):

and
wherein:
R 7 to R 10 individually represent hydrogen or an electron-withdrawing group.

17. The organometallic complex according to claim 14 ,
wherein the organometallic complex is represented by General Formula (G8):

and
wherein:
R 11 represents a cycloalkyl group having 5 to 8 carbon atoms;
R 12 to R 16 individually represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, and a phenyl group; and
R 17 to R 20 individually represent hydrogen or an electron-withdrawing group.

18. The organometallic complex according to claim 17 , wherein the electron-withdrawing group is a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group substituted by a fluoro group, or a phenyl group substituted by a trifluoromethyl group.

19. The

Assignees

• Inoue Hideko
• Nakagawa Tomoka
• Ohsawa Nobuharu
• Seo Satoshi
• Yamada Yui
• Semiconductor Energy Lab

Inventors

• Inoue Hideko
• Nakagawa Tomoka
• Ohsawa Nobuharu
• Seo Satoshi
• Yamada Yui

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09B57/10

  Metal complexes of organic compounds not being dyes in uncomplexed form · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title