Method for producing cyclometalated iridium complex, and cyclometalated iridium complex precursor including organoiridium material

Patent metadata

Field	Value
Publication number	US-10538543-B2
Application number	US-201716331978-A
Country	US
Kind code	B2
Filing date	Oct 12, 2017
Priority date	Oct 24, 2016
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

The present invention provides a method for producing a cyclometalated iridium complex, the method including producing a cyclometalated iridium complex by reacting a cyclometalated iridium complex raw material including an organoiridium material with an aromatic heterocyclic bidentate ligand capable of forming an iridium-carbon bond and an iridium-nitrogen bond, and using as the raw material an organoiridium material represented by the following general formula (1). The present invention allows a cyclometalated iridium complex to be produced with a high yield without by-production of a halogen-crosslinked iridium dimer.

First claim

The invention claimed is:

1. A method for producing a cyclometalated iridium complex represented by the following Formula (3), the method comprising producing a cyclometalated iridium complex by reacting a cyclometalated iridium complex raw material including an organoiridium material represented by the following Formula (1) with an aromatic heterocyclic bidentate ligand capable of forming an iridium-carbon bond and represented by the following Formula (2) and an iridium-nitrogen bond,
wherein the aromatic heterocyclic bidentate ligand represented by the Formula (2) is reacted with 1.5 times or more and less than 3 times the molar amount of the iridium compound represented by the Formula (1);

(in Formula (1), Ir represents an iridium atom, and O represents an oxygen atom; L represents a ligand capable of forming an iridium-oxygen bond; R 1 , R 3 , R 4 , R 6 , R 7 and R 9 each independently represent an alkyl group; R 2 , R 5 and R 8 each independently represent a hydrogen atom or an alkyl group; and some or all of hydrogen atoms of the alkyl group may be substituted with halogen atoms),

(in Formula (2), N represents a nitrogen atom, C represents a carbon atom, H represents a hydrogen atom, CyA represents a five-membered or six-membered cyclic group containing nitrogen atoms, CyB represents a five-membered or six-membered cyclic group containing carbon atoms, and CyA and CyB may be linked together to form a ring structure), and

(in Formula (3), Ir represents an iridium atom, N represents a nitrogen atom, C represents a carbon atom, CyA represents a five-membered or six-membered cyclic group containing nitrogen atoms, and is linked to iridium via the nitrogen atoms, and CyB represents a five-membered or six-membered cyclic group containing carbon atoms, and is linked to iridium via the carbon atoms; CyA and CyB may be linked together to further form a ring structure; R 10 and R 12 each independently represent an alkyl group, R 11 s each independently represent a hydrogen atom or an alkyl group, and some or all of hydrogen atoms of the alkyl group may be substituted with halogen atoms; m is 2, and n is 1).

2. The method for producing a cyclometalated iridium complex according to claim 1 , wherein R 2 , R 5 , R 8 and R 11 each independently represent a hydrogen atom.

3. The method for producing a cyclometalated iridium complex according to claim 1 , wherein the ligand L is H 2 O.

4. The method for producing according to claim 2 , wherein CyA is any one of a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring, and
CyB is any one of a benzene ring, a naphthalene ring, an anthracene ring, a carbazole ring, a fluorene ring, a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring.

5. The method for producing a cyclometalated iridium complex according to claim 2 , wherein the ligand L is H 2 O.

6. The method for producing according to claim 3 , wherein CyA is any one of a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring, and
CyB is any one of a benzene ring, a naphthalene ring, an anthracene ring, a carbazole ring, a fluorene ring, a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, an imidazole ring, a pyrazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring.

Assignees

• Aist
• Tanaka Precious Metal Ind

Inventors

• Konno Hideo
• Taniuchi Junichi
• Kobayashi Rumi
• Masahiro Yasushi

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07F15/00

  Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table · CPC title