IP Library › Granted Patent US 9,978,962
Granted Patent B2
US 9,978,962 · App. 14/725,332 · Granted May 22, 2018

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

Inventors: Hideko Inoue (Kanagawa, JP); Tomoka Hara (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Toshiki Sasaki (Kanagawa, JP); Kunihiko Suzuki (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0085C07F15/0033C09K11/06H05B33/14C09K2211/1007C09K2211/1044C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 9,978,962
App. No.
14/725,332
Granted
May 22, 2018
Kind
B2
Abstract

To provide a long-lifetime organometallic iridium complex exhibiting yellow light emission with high emission efficiency as a novel substance. The organometallic iridium complex includes a ligand in which an unsubstituted phenyl group is bonded to each of the 2-position and the 5-position of pyrimidine. The organometallic iridium complex has a structure represented by General Formula (G1).

Claims (59)

1. A compound comprising:

a pyrimidine ring; and

a first phenyl group and a second phenyl group each bonded to the pyrimidine ring,

wherein the first phenyl group is bonded to an iridium atom,

wherein the pyrimidine ring is bonded to the iridium atom by a coordinate bond,

wherein a dihedral angle between the pyrimidine ring and the second phenyl group is from −20° to −60° in a stable structure of the compound when the compound is in a singlet ground state,

wherein the dihedral angle is from −10° to −50° in a stable structure of the compound when the compound is in a lowest triplet excited state,

wherein the first phenyl group is bonded to a 2-position of the pyrimidine ring, and

wherein the second phenyl group is bonded to a 5-position of the pyrimidine ring.

2. The compound according to claim 1 , wherein an emission spectrum of the compound has a first peak in a range of 550 nm to 580 nm and a second peak in a range of 570 nm to 630 nm.

3. A light-emitting element comprising:

a first electrode and a second electrode; and

an electroluminescent layer between the first electrode and the second electrode,

wherein the electroluminescent layer comprises the compound according to claim 1 .

4. A light-emitting device comprising:

the light-emitting element according to claim 3 ; and

a transistor electrically connected to the light-emitting element.

5. An electronic device comprising:

the light-emitting device according to claim 4 ; and

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

6. A lighting device comprising:

the light-emitting element according to claim 3 ; and

a support base,

wherein the light-emitting element is over the support base.

7. A light-emitting element comprising:

a first electrode and a second electrode; and

a light-emitting layer between the first electrode and the second electrode,

wherein the light-emitting layer comprises the compound according to claim 1 .

8. The light-emitting element according to claim 7 , wherein the light-emitting layer comprises a first organic compound and a second organic compound.

9. A compound comprising a structure represented by General Formula (G1):

10. The compound according to claim 9 , the compound represented by General Formula (G2):

wherein L represents a monoanionic ligand.

11. The compound according to claim 10 , wherein the monoanionic ligand is a monoanionic bidentate chelate ligand in which two ligand elements are both oxygen or nitrogen.

12. The compound according to claim 10 ,

wherein the monoanionic ligand is represented by General Formula (L1) or (L2):

wherein each of R 1 to R 7 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,

wherein each of A 1 to A 3 independently represents nitrogen, sp2 hybridized carbon bonded to hydrogen, or sp2 hybridized carbon having a substituent, and

wherein the substituent represents 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.

13. The compound according to claim 9 , the compound represented by Structural Formula (100):

14. The compound according to claim 9 , wherein an emission spectrum of the compound has a first peak in a range of 550 nm to 580 nm and a second peak in a range of 570 nm to 630 nm.

15. A light-emitting element comprising:

a first electrode and a second electrode; and

an electroluminescent layer between the first electrode and the second electrode,

wherein the electroluminescent layer comprises the compound according to claim 9 .

16. A light-emitting device comprising:

the light-emitting element according to claim 15 ; and

a transistor electrically connected to the light-emitting element.

17. An electronic device comprising:

the light-emitting device according to claim 16 ; and

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

18. A lighting device comprising:

the light-emitting element according to claim 15 ; and

a support base,

wherein the light-emitting element is over the support base.

19. A light-emitting element comprising:

a first electrode and a second electrode; and

a light-emitting layer between the first electrode and the second electrode,

wherein the light-emitting layer comprises the compound according to claim 9 .

20. The light-emitting element according to claim 19 , wherein the light-emitting layer comprises a first organic compound and a second organic compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2015
From: INOUE, HIDEKO; HARA, TOMOKA; SEO, SATOSHI; SASAKI, TOSHIKI; SUZUKI, KUNIHIKO
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 035971/0101 →
Priority Claims (1)
JP 2014-112278 · May 30, 2014 · national
Continuity (1)
Related Publication 20150349278A1 · Dec 3, 2015