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

Patent metadata

Field	Value
Publication number	US-9978960-B2
Application number	US-201414300695-A
Country	US
Kind code	B2
Filing date	Jun 10, 2014
Priority date	Jun 14, 2013
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

An organometallic iridium complex that has high emission efficiency and a long lifetime and emits deep red light (emission wavelength: around 700 nm) is provided. The organometallic iridium complex has a ligand that is represented by General Formula (G0) and has at least a dimethyl phenyl group and a quinoxaline skeleton.

In the formula, R 1 to R 3 separately represent an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a phenyl group having an alkyl group having 1 to 6 carbon atoms as a substituent.

First claim

The invention claimed is:

1. A compound represented by Formula (G1):

wherein:
L represents a monoanionic ligand,
R 1 and R 2 separately represent a methyl group, an ethyl group, an isobutyl group, or a neopentyl group,
R 3 represents a methyl group, an ethyl group, an isobutyl group, a 3,5-dimethylphenyl group, a 2-methylphenyl group, a 2,6-dimethylphenyl group, or a 3,5-diethylphenyl group, the monoanionic ligand is a ligand represented by Formula (L1)

and
R 71 and R 73 represent a substituted or unsubstituted alkyl group having 3 to 6 carbon atoms, and R 72 represents hydrogen.

2. The compound according to claim 1 , wherein the compound is represented by any of Formulae (100), and (118):

3. A light-emitting device comprising:
a layer between a pair of electrodes, the layer comprising a compound represented by Formula (G1):

wherein:
L represents a monoanionic ligand,
R 1 and R 2 separately represent a methyl group, an ethyl group, an isobutyl group, or a neopentyl group, and
R 3 represents a methyl group, an ethyl group, an isobutyl group, a 3,5-dimethylphenyl group, a 2-methylphenyl group, a 2,6-dimethylphenyl group, or a 3,5-diethylphenyl group.

4. The light-emitting device according to claim 3 , wherein the monoanionic ligand is any of a monoanionic bidentate chelate ligand having a beta-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 ligand elements are both nitrogen.

5. The light-emitting device according to claim 4 ,
wherein:
the monoanionic ligand is a ligand represented by any of Formulae (L1) to (L7):

R 71 to R 111 separately represent 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,
A 1 to A 3 separately represent nitrogen, sp 2 hybridized carbon bonded to hydrogen, or sp 2 hybridized carbon having a substituent, and
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.

6. The light-emitting device according to claim 3 ,
wherein:
the compound is represented by Formula (G2):

and
R 4 and R 5 separately represent 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 device according to claim 3 , wherein the compound is represented by any of Formulae (100), (114), and (118):

8. A lighting device comprising the light-emitting device according to claim 3 .

Assignees

• Semiconductor Energy Lab

Inventors

• Inoue Hideko
• Yamaguchi Tomoya
• Seo Hiromi
• Takahashi Tatsuyoshi
• Seo Satoshi

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/0085 Primary

  Electricity · mapped topic

• H10K85/342 Primary

  comprising iridium · CPC title