Raw material and production method for cyclometalated iridium complex

Patent metadata

Field	Value
Publication number	US-10053479-B2
Application number	US-201415109927-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Jan 10, 2014
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

The present invention relates to a raw material for a cyclometalated iridium complex, and provides a technique that makes it possible to obtain a cyclometalated iridium complex in higher yield at a lower reaction temperature than using tris(2,4-pentanedionato)iridium(III). The present invention relates to a raw material for a cyclometalated iridium complex, including an organic iridium material for producing a cyclometalated iridium complex, the organic iridium material being a tris(β-diketonato)iridium(III), in which an asymmetric β-diketone is coordinated to iridium.

First claim

The invention claimed is:

1. A method for producing a cyclometalated iridium complex, comprising the step of reacting a raw material for a cyclometalated iridium complex including an organic iridium material and one or more aromatic heterocyclic bidentate ligand of Chemical Formula 2 in a solvent having a boiling point at normal pressure of 160° C. to 300° C., wherein the reaction temperature is 100° C. to 300° C., thereby producing a facial isomer of any one of triscyclometalated iridium complex of Chemical Formula 3, in which three aromatic heterocyclic bidentate ligands are coordinated to the iridium atom,
wherein the raw material comprises an organic iridium material which is a tris(β-diketonato)iridium(III) represented by Chemical Formula 1, in which an asymmetric β-diketone is coordinated to iridium,

wherein in Chemical Formula 1, O represents an oxygen atom; R a and R b are each an alkyl group of C 1-5 , and R a and R b are not the same; either R a or R b is a methyl group; and R c is a hydrogen atom, and wherein in Chemical Formula 2, R 1 to R 48 each represent a hydrogen atom, an alkyl group, an aryl group, or a halogen atom; and * indicates a site of bonding to iridium.

2. The method for producing a cyclometalated iridium complex according to claim 1 , wherein the raw material and the aromatic heterocyclic bidentate ligand are reacted in the presence of acetic acid, oxalic acid, valeric acid, butyric acid, tartaric acid, hydrochloric acid, sulfuric acid, or phosphoric acid.

3. The method for producing a cyclometalated iridium complex according to claim 1 , wherein R a and R b are each an aliphatic hydrocarbon group.

4. The method for producing a cyclometalated iridium complex according to claim 1 , wherein R a and R b are each a linear or branched hydrocarbon group.

5. The method for producing a cyclometalated iridium complex according to claim 1 , wherein the β-diketone is 5-methyl-2,4-hexanedione or 2,4-octanedione.

6. A method for producing a cyclometalated iridium complex, comprising the step of reacting a raw material for a cyclometalated iridium complex including an organic iridium material and one or more aromatic heterocyclic bidentate ligand of Chemical Formula 2 without solvent, wherein the reaction temperature is 200° C. to 300° C., thereby producing a facial isomer of any one of triscyclometalated iridium complex of Chemical Formula 3, in which three aromatic heterocyclic bidentate ligands are coordinated to the iridium atom,
wherein the raw material comprises an organic iridium material which is a tris(β-diketonato)iridium(III) represented by Chemical Formula 1, in which an asymmetric β-diketone is coordinated to iridium,

wherein in Chemical Formula 1, O represents an oxygen atom; R a and R b are each an alkyl group of C 1-5 , and R a and R b are not the same; either R a or R b is a methyl group; and R c is a hydrogen atom, and wherein R 1 to R 48 each represent a hydrogen atom, an alkyl group, an aryl group, or a halogen atom; and * indicates a site of bonding to iridium.

Assignees

• Tanaka Precious Metal Ind
• Aist

Inventors

• Konno Hideo
• Taniuchi Junichi
• Harada Ryosuke
• SHIGETOMI Toshiyuki
• Masahiro Yasushi

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07C49/92 Primary

  Ketonic chelates · CPC title

• C07F15/004

  without a metal-carbon linkage · CPC title