Iridium organometallic complexes comprising 4-arylpyrimidines

Patent metadata

Field	Value
Publication number	US-9985223-B2
Application number	US-201514934566-A
Country	US
Kind code	B2
Filing date	Nov 6, 2015
Priority date	Oct 22, 2010
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R 3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

First claim

What is claimed is:

1. An organometallic complex represented by formula (G4),

wherein L represents a monoanionic ligand,
wherein R 1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group,
wherein the substituted phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
wherein Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms,
wherein the substituted arylene group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms, and
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 nitrogen atoms coordinate to the Ir atom.

2. The organometallic complex according to claim 1 ,
wherein the organometallic complex is represented by formula (G5),

wherein R 4 , R 5 , R 6 , and R 7 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , and R 7 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.

3. The organometallic complex according to claim 1 ,
wherein the organometallic complex is represented by formula (G6),

wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.

4. The organometallic complex according to claim 1 ,
wherein L represents any one of formulae (L1), (L2), (L3), (L4), (L5), (L6), and (L7),

wherein R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 , R 87 , R 88 , R 89 , R 90 , R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 , R 100 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 , and R 109 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen, a vinyl group, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having 1 to 4 carbon atoms,
wherein A 1 , A 2 , and A 3 individually represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to a substituent R, and
wherein the substituent R represents any of an alkyl group having 1 to 4 carbon atoms, a halogen, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.

5. A light-emitting element comprising a light-emitting layer between a pair of electrodes,
wherein the light-emitting layer comprises the organometallic complex according to claim 1 .

6. An electronic device comprising a light-emitting device comprising the light-emitting element according to claim 5 in a display portion.

7. A lighting device comprising a light-emitting device comprising the light-emitting element according to claim 5 in a light-emitting portion.

Assignees

• Semiconductor Energy Lab

Inventors

• Inoue Hideko
• Yamaguchi Tomoya
• Shitagaki Satoko
• Ushikubo Takahiro
• Seo Satoshi
• Yamada Yui
• Nowatari Hiromi

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title