Benzidine derivative, method for producing benzidine derivative, and electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-9817325-B2
Application number	US-201615214908-A
Country	US
Kind code	B2
Filing date	Jul 20, 2016
Priority date	Jul 29, 2015
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

A benzidine derivative is represented by general formula (1). In the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each represent, independently of one another, a hydrogen atom, a halogen atom, an optionally substituted alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 14. n represents an integer of at least 0 and no greater than 2.

First claim

What is claimed is:

1. An electrophotographic photosensitive member comprising a conductive substrate and a photosensitive layer, wherein
the photosensitive layer contains at least a charge generating material and a benzidine derivative represented by general formula (1) shown below as a hole transport material,

wherein in the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each represent, independently of one another, a hydrogen atom, a halogen atom, an optionally substituted alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 14, and n represents an integer of at least 0 and no greater than 2.

2. The electrophotographic photosensitive member according to claim 1 , comprising, as the photosensitive layer:
a charge generating layer containing the charge generating material and a charge transport layer containing the hole transport material; or
a single-layer type photosensitive layer containing the charge generating material and the hole transport material, wherein
the charge generating material is titanyl phthalocyanine having a Y-form crystal structure.

3. The electrophotographic photosensitive member according to claim 1 , wherein
the photosensitive layer is a single-layer type photosensitive layer,
the single-layer type photosensitive layer contains the charge generating material, the hole transport material, and an electron transport material, and
the electron transport material is a compound represented by general formula (12) shown below

where in the general formula (12), R 11 , R 12 , R 13 , and R 14 each represent, independently of one another, a hydrogen atom, a cyano group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, an optionally substituted aryl group, or an optionally substituted heterocyclic group.

4. The electrophotographic photosensitive member according to claim 1 , wherein in the general formula (1), R 6 , R 7 , R 8 , R 9 , and R 10 each represent a hydrogen atom.

5. The electrophotographic photosensitive member according to claim 1 , wherein in the general formula (1), n represents 1 or 2.

6. The electrophotographic photosensitive member according to claim 1 , wherein
in the general formula (1),
R 1 , R 2 , R 3 , R 4 , and R 5 each represent, independently of one another, a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 6 and optionally having an aryl group having a carbon number of at least 6 and no greater than 14, or an aryl group having a carbon number of at least 6 and no greater than 14,
R 6 , R 7 , R 8 , R 9 , and R 10 each represent, independently of one another, a hydrogen atom or an alkoxy group having a carbon number of at least 1 and no greater than 6, and
n represents 0 or 1.

7. The electrophotographic photosensitive member according to claim 1 , wherein
the benzidine derivative represented by the general formula (1) is a benzidine derivative represented by chemical formula (HT-1), (HT-2), (HT-3), (HT-4), (HT-5), or (HT-6) shown below

Assignees

• Kyocera Document Solutions Inc

Inventors

• Okada Hideki

Classifications

• G03G5/0614 Primary

  Amines · CPC title

• G03G5/0672 Primary

  containing two or more methine or polymethine groups · CPC title

• G03G5/0696

  Phthalocyanines · CPC title

• C07C211/54

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

• G03G5/061443 Primary

  benzidine · CPC title