IP Library Granted Patent US 9,309,458
Granted Patent B2
US 9,309,458 · App. 13/770,188 · Granted Apr 12, 2016

Phosphorescent organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Hideko Inoue (Atsugi, JP); Takahiro Ishisone (Atsugi, JP); Nobuharu Ohsawa (Tochigi, JP); Satoshi Seo (Sagamihara, JP); Takao Hamada (Atsugi, JP)
Assignee: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
C09K11/06C07F15/0033H01L51/0085H05B33/14C09K2211/1059C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 9,309,458
App. No.
13/770,188
Granted
Apr 12, 2016
Kind
B2
Abstract

A novel phosphorescent organometallic iridium complex is provided in which a coordination position of a ligand with respect to a metal can be controlled in synthesis. A novel phosphorescent organometallic iridium complex is provided which can keep high quantum efficiency and can emit phosphorescence in the blue to green wavelength region. A phosphorescent organometallic iridium complex which includes a structure represented by General Formula (G1) and whose ligand is a 4H-1,2,4-triazole compound which has an unsubstituted phenyl group at the 3-position, a substituted or unsubstituted phenyl group at the 4-position, and a phenyl group at the 5-position. In the phenyl group at the 5-position, an alkyl group is bonded to at least one of the ortho-positions, and the other of the ortho-positions, the meta-positions, and the para-position are substituted or unsubstituted.

Claims (47)

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

wherein:

R 1 represents an alkyl group having 1 to 6 carbon atoms; and

R 2 to R 10 independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms.

2. The complex according to claim 1 , wherein the complex is represented by Formula (G2):

3. The complex according to claim 1 , wherein the complex is represented by any one of Formulae (100), (101), (105), (112), and (121):

4. A light-emitting device comprising a complex,

wherein:

the complex is represented by Formula (G1);

R 1 represents an alkyl group having 1 to 6 carbon atoms; and

R 2 to R 10 independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms.

5. The light-emitting device according to claim 4 , wherein the complex is represented by Formula (G2):

6. The light-emitting device according to claim 4 , wherein the complex is represented by any one of Formulae (100), (101), (105), (112), and (121):

7. An electronic device comprising the light-emitting device according to claim 4 .

8. A lighting device comprising the light-emitting device according to claim 4 .

9. A light-emitting device comprising a light-emitting layer,

wherein:

the light-emitting layer comprises a complex represented by Formula (G1) and a first organic compound;

R 1 represents an alkyl group having 1 to 6 carbon atoms; and

R 2 to R 10 independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms.

10. The light-emitting device according to claim 9 , wherein the complex is represented by Formula (G2):

11. The light-emitting device according to claim 9 , wherein the complex is represented by any one of Formulae (100), (101), (105), (112), and (121):

12. The light-emitting device according to claim 9 , wherein the first organic compound is selected from an aromatic amine, a carbazole derivative, a nitrogen-containing heterocyclic compound, and a metal complex.

13. The light-emitting device according to claim 9 , further comprising a second organic compound in the light-emitting layer,

wherein:

the first organic compound is a nitrogen-containing heteroaromatic compound; and

the second organic compound is selected from a carbazole derivative, an indole derivative and an aromatic amine.

14. An electronic device comprising the light-emitting device according to claim 9 .

15. A lighting device comprising the light-emitting device according to claim 9 .

16. A light-emitting device comprising a first light-emitting layer and a second light-emitting layer over the first light-emitting layer,

wherein:

the first light-emitting layer comprises a first complex, a first compound, and a second compound;

the second light-emitting layer comprises a second complex and the first compound;

each of the first complex and the second complex is represented by Formula (G1);

R 1 represents an alkyl group having 1 to 6 carbon atoms; and

R 2 to R 10 independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms.

17. The light-emitting device according to claim 16 , wherein each of the first complex and the second complex is represented by Formula (G2):

18. The light-emitting device according to claim 16 , wherein each of the first complex and the second complex is represented by any one of Formulae (100), (101), (105), (112), and (121):

19. The light-emitting device according to claim 16 ,

wherein:

the first compound is a nitrogen-containing heteroaromatic compound; and

the second compound is selected from a carbazole derivative, an indole derivative, and an aromatic amine.

20. The light-emitting device according to claim 16 , wherein the first complex is different from the second complex.

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

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

23. The light-emitting device according to claim 16 , comprising a charge generation layer between the first light-emitting layer and the second light-emitting layer.

24. The light-emitting device according to claim 9 , wherein the first organic compound is 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2013
From: INOUE, HIDEKO; ISHISONE, TAKAHIRO; OHSAWA, NOBUHARU; SEO, SATOSHI; HAMADA, TAKAO
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 029830/0113 →
Priority Claims (1)
JP 2012-038535 · Feb 24, 2012 · national
Continuity (1)
Related Publication 20130221278A1 · Aug 29, 2013