IP Library › Granted Patent US 10,096,786
Granted Patent B2
US 10,096,786 · App. 14/974,142 · Granted Oct 9, 2018

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

Inventors: Yui Yamada (Kanagawa, JP); Hideko Inoue (Kanagawa, JP); Hiromi Seo (Kanagawa, JP); Tatsuyoshi Takahashi (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0085C07F15/0033C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,096,786
App. No.
14/974,142
Granted
Oct 9, 2018
Kind
B2
Abstract

To provide an organometallic complex with high emission efficiency and high heat resistance, which emits yellow green light. The organometallic complex includes a metal and a ligand which is a benzo[h]quinazoline skeleton including a condensed ring bonded to benzo[h]quinazoline through a carbon-carbon bond between the 5-position and the 6-position. The organometallic complex has a structure represented by General Formula (G1). In General Formula (G1), M represents a metal belonging to Group 9 or 10; each of R 1 to R 4 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 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. A ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

Claims (53)

1. An organometallic complex comprising:

a metal belonging to Group 9 or 10; and

a benzo[h] quinazoline skeleton,

wherein the benzo[h]quinazoline skeleton comprises a condensed ring sharing a carbon-carbon bond between a 5-position and a 6-position with a benzo[h]quinazoline, and

wherein the benzo[h]quinazoline skeleton is bonded to the metal.

2. The organometallic complex according to claim 1 ,

wherein the organometallic complex further comprises a ligand selected from a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, and a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen, and

wherein the ligand is bonded to the metal.

3. The organometallic complex according to claim 1 ,

wherein the condensed ring is a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

4. An organometallic complex comprising a structure represented by Formula (G1),

wherein M represents a metal belonging to Group 9 or 10,

wherein each of R 1 to R 4 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,

wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, and

wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

5. The organometallic complex according to claim 4 ,

wherein the organometallic complex is represented by Formula (G2),

wherein M represents a metal belonging to Group 9 or 10,

wherein L represents a monoanionic ligand,

wherein each of R 1 to R 4 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,

wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group,

wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen,

wherein m is 3 and n is 1, 2, or 3, when the metal belongs to Group 9, and

wherein m is 2 and n is 1 or 2, when the metal belongs to Group 10.

6. The organometallic complex according to claim 5 ,

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

7. The organometallic complex according to claim 5 ,

wherein the monoanionic ligand is represented by any of Formulae (L1) to (L7),

wherein each of R 71 to R 109 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, and

wherein each of A 1 to A 3 independently represents nitrogen, sp 2 hybridized carbon bonded to hydrogen, or sp 2 hybridized carbon having a substituent, the substituent being an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

8. The organometallic complex according to claim 4 ,

wherein the organometallic complex is represented by Formula (G3),

wherein each of R 1 to R 4 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,

wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group,

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

wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

9. The organometallic complex according to claim 4 ,

wherein the organometallic complex is represented by Formula (G4),

wherein each of R 1 to R 4 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,

wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, and

wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

10. The organometallic complex according to claim 4 ,

wherein the organometallic complex is represented by any one of Formulae (100), (101), (104), and (114),

11. A light-emitting element comprising an electroluminescence layer between a pair of electrodes, the electroluminescence layer comprising the organometallic complex according to claim 4 .

12. A light-emitting device comprising:

the light-emitting element according to claim 11 ; and

at least one of a transistor and a substrate.

13. An electronic device comprising:

the light-emitting device according to claim 12 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

14. A lighting device comprising:

the light-emitting device according to claim 12 ; and

a housing.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2015
From: YAMADA, YUI; INOUE, HIDEKO; SEO, HIROMI; TAKAHASHI, TATSUYOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 037326/0284 →
Priority Claims (1)
JP 2014-256995 · Dec 19, 2014 · national
Continuity (1)
Related Publication 20160181550A1 · Jun 23, 2016
Cited By (1)
US 12,745,558