IP Library Granted Patent US 9,130,184
Granted Patent B2
US 9,130,184 · App. 13/457,877 · Granted Sep 8, 2015

Light-emitting device, electronic device, and lighting device utilizing phosphorescence

Inventors: Satoshi Seo (Kanagawa, JP); Hideko Inoue (Kanagawa, JP); Hiromi Seo (Kanagawa, JP); Tomoya Yamaguchi (Kanagawa, JP); Satoko Shitagaki (Kanagawa, JP); Takahiro Ushikubo (Tochigi, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/5016C09K11/06H01L51/0085C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/185H01L27/3206H01L27/3209H01L51/5068H01L51/5265H01L51/5278H01L2251/5361H01L2251/5384
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Quick Facts
Patent No.
US 9,130,184
App. No.
13/457,877
Granted
Sep 8, 2015
Kind
B2
Abstract

A new light-emitting device utilizing phosphorescence is provided. Further, an electronic device and a lighting device which utilize phosphorescence are provided. One embodiment of the present invention is a light-emitting device including a phosphorescent organometallic iridium complex comprising iridium and either pyrimidine having an aryl group at the 4-position or 1,3,5-triazine having an aryl group at the 2-position. One of nitrogen in the pyrimidine or 1,3,5-triazine is coordinated to the iridium. Also, each of the pyrimidine and 1,3,5-triazine has a substituent such as an alkyl group or an aryl group. Further the ortho position of the aryl group which is bonded to the 4-position of the pyrimidine or the 2-position of the 1,3,5-triazine is bonded to the iridium.

Claims (76)

1. A light-emitting device comprising:

a light-emitting layer comprising an iridium complex having a pyrimidine ligand, a first organic compound, and a second organic compound,

wherein:

the pyrimidine ligand has an aryl group at a 4-position,

nitrogen at a 3-position of the pyrimidine ligand is coordinated to iridium;

the pyrimidine ligand has an alkyl group or an aryl group at any one of a 2-position, a 5-position, and a 6-position;

an ortho position of the aryl group which is bonded to the 4-position of the pyrimidine ligand is bonded to the iridium, and

the first organic compound and the second organic compound are selected so as to form an exciplex.

2. The light-emitting device according to claim 1 ,

wherein:

the iridium complex is represented by any one of the following formulae:

L represents a monoanionic ligand;

Ar represents a substituted or unsubstituted aryl group;

R 1 to R 3 separately represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and

at least one of R 1 to R 3 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

3. The light-emitting device according to claim 2 ,

wherein:

the monoanionic ligand is represented by any of the formulae (L1) to (L7):

R 21 to R 58 separately represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, and a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms; and

A 1 to A 4 separately represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to any of an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.

4. The light-emitting device according to claim 1 ,

wherein the iridium complex is represented by any one of the following formulae:

5. The light-emitting device according to claim 1 , further comprising a second light-emitting layer.

6. The light-emitting device according to claim 1 , further comprising:

a reflective electrode;

a transparent conductive layer over and in contact with the reflective electrode; and

a semi-transmissive and semi-reflective electrode over the transparent conductive layer,

wherein the light-emitting layer is located between the transparent conductive layer and the semi-transmissive and semi-reflective electrode.

7. The light-emitting device according to claim 6 , further comprising a second light-emitting layer,

wherein the second light-emitting layer is located between the transparent conductive layer and the light-emitting layer or between the light-emitting layer and the semi-transmissive and semi-reflective electrode.

8. The light-emitting device according to claim 1 , further comprising:

a first electrode;

a second light-emitting layer over the first electrode;

a charge-generation layer over the second light-emitting layer; and

a second electrode over the charge-generation layer,

wherein the light-emitting layer is located between the charge-generation layer and the second electrode.

9. An electronic device comprising the light-emitting device according to claim 1 .

10. A lighting device comprising the light-emitting device according to claim 1 .

11. A light-emitting device comprising:

a light-emitting layer comprising an iridium complex having a 1,3,5-triazine ligand, a first organic compound, and a second organic compound,

wherein:

the 1,3,5-triazine ligand has an aryl group at a 2-position;

nitrogen at a 1-position of the 1,3,5-triazine ligand is coordinated to iridium;

the 1,3,5-triazine ligand has a substituent at a 4-position or a 6-position;

an ortho position of the aryl group which is bonded to the 2-position of the 1,3,5-triazine ligand is bonded to the iridium, and

the first organic compound and the second organic compound are selected so as to form an exciplex.

12. The light-emitting device according to claim 11 ,

wherein:

the iridium complex is represented by any one of the following formulae:

L represents a monoanionic ligand;

Ar represents a substituted or unsubstituted aryl group;

R 4 and R 5 separately represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and

at least one of R 4 and R 5 represents any of a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

13. The light-emitting device according to claim 12 ,

wherein:

the monoanionic ligand is represented by any of the formulae (L1) to (L7):

R 21 to R 58 separately represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, and a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms; and

A 1 to A 4 separately represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to any of an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.

14. The light-emitting device according to claim 11 ,

wherein the iridium complex is represented by any of the following formulae:

15. The light-emitting device according to claim 11 , further comprising a second light-emitting layer.

16. The light-emitting device according to claim 11 , further comprising:

a reflective electrode;

a transparent conductive layer over and in contact with the reflective electrode;

a semi-transmissive and semi-reflective electrode over the transparent conductive layer,

wherein the light-emitting layer is located between the transparent conductive layer and the semi-transmissive and semi-reflective electrode.

17. The light-emitting device according to claim 16 , further comprising a second light-emitting layer,

wherein the second light-emitting layer is located between the transparent conductive layer and the light-emitting layer or between the light-emitting layer and the semi-transmissive and semi-reflective electrode.

18. The light-emitting device according to claim 11 , further comprising:

a first electrode;

a second light-emitting layer over the first electrode;

a charge-generation layer over the second light-emitting layer; and

a second electrode over the charge-generation layer,

wherein the light-emitting layer is located between the charge-generation layer and the second electrode.

19. An electronic device comprising the light-emitting device according to claim 11 .

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2012
From: SEO, SATOSHI; INOUE, HIDEKO; SEO, HIROMI; YAMAGUCHI, TOMOYA; SHITAGAKI, SATOKO; USHIKUBO, TAKAHIRO
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 028502/0361 →
Priority Claims (1)
JP 2011-102566 · Apr 29, 2011 · national
Continuity (1)
Related Publication 20120274201A1 · Nov 1, 2012