IP Library › Granted Patent US 10,388,891
Granted Patent B2
US 10,388,891 · App. 15/085,390 · Granted Aug 20, 2019

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

Inventors: Tomoya Yamaguchi (Kanagawa, JP); Hideko Inoue (Kanagawa, JP); Tatsuyoshi Takahashi (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0085C07F15/0033C09K11/06H05B33/14C09K2211/1007C09K2211/1059C09K2211/185H01L2251/308
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Quick Facts
Patent No.
US 10,388,891
App. No.
15/085,390
Granted
Aug 20, 2019
Kind
B2
Abstract

As a novel substance having a novel skeleton, an organometallic complex with high emission efficiency is provided. The organometallic complex includes a metal and a ligand. The metal is iridium or platinum. The ligand includes a 5H-pyrimido[5,4-b]indole skeleton and an aryl group bonded to the 4-position of the 5H-pyrimido[5,4-b]indole skeleton. The 3-position of the 5H-pyrimido[5,4-b]indole skeleton and the aryl group are bonded to the metal. In the formula, M represents iridium or platinum. In addition, Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and each of R 1 to R 6 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

Claims (67)

1. A light-emitting element comprising a light-emitting layer,

wherein the light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex,

wherein the organometallic complex comprises a metal and a first ligand,

wherein the first ligand comprises a 5H-pyrimido[5,4-b]indole skeleton and an aryl group bonded to a 4-position of the 5H-pyrimido[5,4-b]indole skeleton,

wherein the metal is iridium or platinum,

wherein a 3-position of the 5H-pyrimido [5,4-b]indole skeleton and the aryl group are bonded to the metal, and

wherein a 5-position of the 5H-pyrimido[5,4-b]indole skeleton is bonded to an ethyl groups, and wherein the aryl group is a substituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

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

wherein the organometallic complex further comprises a second ligand,

wherein the second ligand is a monoanionic bidentate chelate ligand comprising a β-diketone structure, a carboxyl group, a phenolic hydroxyl group, or a structure in which two coordinating elements are both nitrogen, and

wherein the second ligand is bonded to the metal.

3. A light-emitting element comprising a light-emitting layer,

wherein:

the light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex comprising a structure represented by a general formula (G1):

M represents iridium or platinum;

Ar represents a substituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group;

each of R 1 to R 5 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and

R 6 represents an ethyl group.

4. A light-emitting element comprising a light-emitting layer,

wherein:

the light-emitting layer comprises a first organic compound, a second organic compound, and an organometallic complex represented by a general formula (G2):

M represents iridium or platinum;

L represents a monoanionic ligand;

Ar represents a substituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group;

each of R 1 to R 5 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms;

R 6 represents an ethyl group;

when M represents iridium, m is 3 and n is 2 or 3; and

when M represents platinum, m is 2 and n is 1 or 2.

5. The light-emitting element according to claim 4 ,

wherein the monoanionic ligand is a monoanionic bidentate chelate ligand comprising a β-diketone structure, a monoanionic bidentate chelate ligand comprising a carboxyl group, a monoanionic bidentate chelate ligand comprising a phenolic hydroxyl group, or a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen.

6. The light-emitting element according to claim 4 ,

wherein:

the monoanionic ligand is represented by a general foimulae (L1);

each of R 71 to R 73 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms.

7. The light-emitting element according to claim 4 ,

wherein:

the organometallic complex is represented by a general formula (G3); and

each of R 7 and R 8 independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

8. The light-emitting element according to claim 4 ,

wherein

the organometallic complex is represented by a general formula (G4),

9. The light-emitting element according to claim 4 , wherein the organometallic complex is represented by a structural formula (100),

10. The light-emitting element according to claim 4 , wherein the organometallic complex is represented by a structural formula (127),

11. The light-emitting element according to claim 4 ,

wherein the first organic compound is a carbazole derivative.

12. A light-emitting device comprising:

the light-emitting element according to claim 4 ; and

a transistor or a substrate.

13. An electronic device comprising:

the light-emitting device according to claim 12 ; and

a microphone, a camera, an operation button, an external connection portion, or a speaker.

14. A lighting device comprising:

the light-emitting device according to claim 12 ; and

a housing, a cover, or a support.

15. The light-emitting element according to claim 1 , wherein the first organic compound is a carbazole derivative.

16. The light-emitting element according to claim 3 , wherein the first organic compound is a carbazole derivative.

17. A light-emitting element comprising an organometallic complex,

wherein the organometallic complex comprises a metal and a first ligand,

wherein the first ligand comprises a 5H-pyrimido[5,4-b]indole skeleton and an aryl group bonded to a 4-position of the 5H-pyrimido[5,4-b]indole skeleton,

wherein the metal is iridium or platinum,

wherein a 3-position of the 5H-pyrimido[5,4-b]indole skeleton and the aryl group are bonded to the metal,

wherein a 5-position of the 5H-pyrimido[5,4-b]indole skeleton is bonded to an ethyl group, and

wherein the aryl group is a substituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

18. The light-emitting element according to claim 17 ,

wherein the organometallic complex further comprises a second ligand,

wherein the second ligand is a monoanionic bidentate chelate ligand comprising a β-diketone structure, a carboxyl group, a phenolic hydroxyl group, or a structure in which two coordinating elements are both nitrogen, and

wherein the second ligand is bonded to the metal.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2016
From: YAMAGUCHI, TOMOYA; INOUE, HIDEKO; TAKAHASHI, TATSUYOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 038141/0043 →
Priority Claims (1)
JP 2015-074799 · Apr 1, 2015 · national
Continuity (1)
Related Publication 20160293863A1 · Oct 6, 2016
Cited By (1)
US 12,745,558