Triphenylamine derivative, method for manufacturing the same, and electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-9376371-B2
Application number	US-201414288542-A
Country	US
Kind code	B2
Filing date	May 28, 2014
Priority date	May 31, 2013
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

A triphenylamine derivative is represented by General Formula (1).

In General Formula (1), OR 1 represents an alkoxy group having 2 to 8 carbon atoms. R 2 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Ar 1 and Ar 2 each independently represent a hydrogen atom, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a 3- to 10-membered heterocyclic group. Note that the case where Ar 1 and Ar 2 are both a hydrogen atom is excluded.

First claim

What is claimed is:

1. A triphenylamine derivative comprising formula (1),

in formula (1),
OR 1 represents an alkoxy group having 2 to 4 carbon atoms,
R 2 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
Ar 1 and Ar 2 each independently represent a hydrogen atom, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a 3- to 10-membered heterocyclic group, and
where Ar 1 and Ar 2 are both a hydrogen atom is excluded.

2. A triphenylamine derivative according to claim 1 , wherein
in formula (1), R 2 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

3. A triphenylamine derivative according to claim 1 , wherein
in formula (1), R 2 represents a hydrogen atom.

4. A triphenylamine derivative according to claim 1 , wherein
in formula (1), R 6 represents a hydrogen atom.

5. A triphenylamine derivative according to claim 1 comprising any one of formulas (8), (9), (10), and (11),

6. An electrophotographic photosensitive member comprising:
a triphenylamine derivative according to claim 1 .

7. A method for manufacturing a triphenylamine derivative according to claim 1 , comprising:
causing a reaction represented by reaction formula (1),

in each of formulas (1) to (3) in reaction formula (1),
X represents a halogen atom,
OR 1 represents an alkoxy group having 2 to 4 carbon atoms,
R 2 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
Ar 1 and Ar 2 each independently represent a hydrogen atom, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms and optionally substituted with an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a 3- to 10-membered heterocyclic group, and
where Ar 1 and Ar 2 are both a hydrogen atom is excluded.

8. A method for manufacturing a triphenylamine derivative according to claim 7 , wherein
a palladium compound is used as a catalyst in the reaction represented by reaction formula (1).

9. A method for manufacturing a triphenylamine derivative according to claim 7 , wherein
the reaction represented by reaction formula (1) is carried out in the presence of a base.

Assignees

• Kyocera Document Solutions Inc

Inventors

• Sugai Fumio
• Kojima Kensuke
• Kitaguchi Kenji
• Okada Hideki

Classifications

• C07C209/10

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• G03G5/0672

  containing two or more methine or polymethine groups · CPC title

• C07C217/92 Primary

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• G03G5/0618

  containing oxygen and nitrogen · CPC title