IP Library › Granted Patent US 9,444,059
Granted Patent B2
US 9,444,059 · App. 14/184,130 · Granted Sep 13, 2016

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

Inventors: Hideko Inoue (Kanagawa, JP); Yui Yamada (Kanagawa, JP); Hiromi Seo (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0085C07F15/0033C09K11/06H01L51/0084H01L51/0087C09K2211/1007C09K2211/1044C09K2211/185H01L51/006H01L51/0059H01L51/0072H01L51/0074H01L51/5016
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Quick Facts
Patent No.
US 9,444,059
App. No.
14/184,130
Granted
Sep 13, 2016
Kind
B2
Abstract

A novel substance capable of emitting phosphorescence is provided. An organometallic complex represented by General Fomulae (G3) or (G5). In the formulae, M represents iridium, platinum, palladium, or rhodium, R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

Claims (69)

1. A compound comprising a structure represented by a formula (G1):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and

M represents a metal.

2. The compound according to claim 1 , wherein the metal is selected from iridium, platinum, palladium, and rhodium.

3. The compound according to claim 1 , wherein the structure is represented by a formula (G2):

4. A compound represented by a formula (G3):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms;

M represents a metal; and

L represents a monoanionic ligand,

wherein:

the metal is selected from iridium, platinum, palladium, and rhodium;

when M represents iridium or rhodium, n is 2; and

when M represents platinum or palladium, n is 1.

5. The compound according to claim 4 , wherein the compound is represented by a formula (G4):

6. The compound according to claim 4 , wherein the monoanionic ligand is a monoanionic bidentate chelate ligand with a beta-diketone structure or a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen.

7. The compound according to claim 6 ,

wherein:

the monoanionic ligand is represented by a formula (L1) or (L2):

R 11 to R 17 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms;

A 1 to A 3 separately represent nitrogen or carbon bonded to hydrogen or a substituent R; and

the substituent R represents an alkyl group having 1 to 6 carbon atoms or a phenyl group.

8. A compound represented by a formula (G5):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and

M represents a metal,

wherein:

the metal is selected from iridium, platinum, palladium, and rhodium;

when M represents iridium or rhodium, n is 2; and

when M represents platinum or palladium, n is 1.

9. The compound according to claim 8 , wherein the compound is represented by a formula (G6):

10. A light-emitting device comprising:

a light emitting layer between a pair of electrodes, the light emitting layer comprising a compound comprising a structure represented by a formula (G1):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and

M represents a metal.

11. The light-emitting device according to claim 10 , wherein the metal is selected from iridium, platinum, palladium, and rhodium.

12. The light-emitting device according to claim 10 , wherein the structure is represented by a formula (G2):

13. A light-emitting device comprising:

a light emitting layer between a pair of electrodes, the light emitting layer comprising a compound represented by a formula (G3):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms;

M represents a metal; and

L represents a monoanionic ligand,

wherein:

the metal is selected from iridium, platinum, palladium, and rhodium;

when M represents iridium or rhodium, n is 2; and

when M represents platinum or palladium, n is 1.

14. The light-emitting device according to claim 13 , wherein the compound is represented by a formula (G4):

15. The light-emitting device according to claim 13 , wherein the monoanionic ligand is a monoanionic bidentate chelate ligand with a beta-diketone structure or a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen.

16. The light-emitting device according to claim 15 ,

wherein:

the monoanionic ligand is represented by a formula (L1) or (L2):

R 11 to R 17 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms;

A 1 to A 3 separately represent nitrogen or carbon bonded to hydrogen or a substituent R; and

the substituent R represents an alkyl group having 1 to 6 carbon atoms or a phenyl group.

17. A light-emitting device comprising:

a light emitting layer between a pair of electrodes, the light emitting layer comprising a compound represented by a formula (G5):

R 1 represents 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 2 to R 7 separately represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and

M represents a metal,

wherein:

the metal is selected from iridium, platinum, palladium, and rhodium;

when M represents iridium or rhodium, n is 2; and

when M represents platinum or palladium, n is 1.

18. The light-emitting device according to claim 17 , wherein the compound is represented by a formula (G6):

19. An electronic appliance comprising the light-emitting device according to claim 10 .

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2014
From: INOUE, HIDEKO; YAMADA, YUI; SEO, HIROMI; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 032246/0880 →
Priority Claims (1)
JP 2013-031622 · Feb 21, 2013 · national
Continuity (1)
Related Publication 20140231770A1 · Aug 21, 2014