Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus

Patent metadata

Field	Value
Publication number	US-9500966-B2
Application number	US-201414480623-A
Country	US
Kind code	B2
Filing date	Sep 8, 2014
Priority date	Sep 30, 2013
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

An electrophotographic photosensitive member, comprising a support, a charge generating layer on the support and a charge transporting layer on the charge generating layer, wherein the charge generating layer comprises a gallium phthalocyanine crystal, a nitrogen-containing heterocyclic compound and a compound represented by Formula (1), wherein a nitrogen atom in a heterocyclic ring of the nitrogen-containing heterocyclic compound has a substituent.

First claim

What is claimed is:

1. An electrophotographic photosensitive member, comprising:
a support;
a charge generating layer on the support; and
a charge transporting layer on the charge generating layer,
wherein the charge generating layer comprises:
a gallium phthalocyanine crystal;
a nitrogen-containing heterocyclic compound; and
a resin having a structural unit represented by Formula (1):

wherein,
X 1 represents a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, or a substituted or unsubstituted butylene group;
R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, a saturated hydrocarbon group or a methoxy group; and
Ar 1 and Ar 2 each independently represent a phenyl group having one or more electron-donating substituents, and
wherein a nitrogen atom in a heterocyclic ring of the nitrogen-containing heterocyclic compound has a substituent, wherein the substituent is a substituted or unsubstituted acyl group, —(C═O)—O—R 1 , a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
wherein a substituent of the substituted acyl group is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
a substituent of the substituted alkyl group, a substituent of the substituted alkenyl group, a substituent of the substituted aryl group and a substituent of the substituted heterocyclic group are a halogen atom, a cyano group, a nitro group, a hydroxy group, a formyl group, an alkyl group, an alkenyl group, an alkoxy group or an aryl group.

2. The electrophotographic photosensitive member according to claim 1 , wherein the nitrogen-containing heterocyclic compound is pyrrole, pyrrolidine, morpholine, piperazine, piperidine, 4-piperidone, indole, phenothiazine, phenoxazine or carbazole.

3. The electrophotographic photosensitive member according to claim 1 , wherein the substituent bonding to an atom other than the nitrogen atom that forms the ring of the nitrogen-containing heterocyclic compound is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a halogen atom, a hydroxy group, a formyl group, an alkenyl group, an alkoxy group or an alkyloxycarbonyl group,
wherein a substituent of the substituted alkyl group, a substituent of the substituted aryl group and a substituent of the substituted heterocyclic group are a halogen atom, a hydroxy group or a formyl group.

4. The electrophotographic photosensitive member according to claim 1 , wherein the nitrogen-containing heterocyclic compound is a compound represented by Formula (2):

wherein R 13 represents a substituted or unsubstituted acyl group, —(C═O)—O—R 11 , a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; a substituent of the substituted acyl group is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; R 11 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
wherein a substituent of the substituted alkyl group, a substituent of the substituted alkenyl group, a substituent of the substituted aryl group and a substituent of the substituted heterocyclic group are a halogen atom, a cyano group, a nitro group, a hydroxy group, a formyl group, an alkyl group, an alkenyl group, an alkoxy group or an aryl group.

5. The electrophotographic photosensitive member according to claim 4 , wherein R 13 in Formula (2) is a methyl group, an ethyl group or a phenyl group.

6. The electrophotographic photosensitive member according to claim 1 , wherein the nitrogen-containing heterocyclic compound is a compound represented by Formula (3):

wherein R 23 and R 24 each independently represent a substituted or unsubstituted acyl group, —(C═O)—O—R 21 , a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; a substituent of the substituted acyl group is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 21 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
wherein a substituent of the substituted alkyl group, a substituent of the substituted alkenyl group, a substituent of the substituted aryl group and a substituent of the substituted heterocyclic group are a halogen atom, a cyano group, a nitro group, a hydroxy group, a formyl group, an alkyl group, an alkenyl group, an alkoxy group or an aryl group.

7. The electrophotographic photosensitive member according to claim 6 , wherein R 23 and R 24 in Formula (3) are each independently a methyl group, an ethyl group or a phenyl group.

8. The electrophotographic photosensitive member according to claim 1 , wherein the nitrogen-containing heterocyclic compound is a compound represented by Formula (4):

wherein R 33 represents a substituted or unsubstituted acyl group, —(C═O)—O—R 31 , a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; a substituent of the substituted acyl group is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 31 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
wherein a substituent of the substituted alkyl group, a substituent of the substituted alkenyl group, a substituent of the substituted aryl group and a substituent of the substituted heterocyclic group are a halogen atom, a cyano group, a nitro group, a hydroxy group, a formyl group, an alkyl group, an alkenyl group, an alkoxy group or an aryl group.

9. The electrophotographic photosensitive member according to claim 8 , wherein R 33 in Formula (4) is a methyl group, an ethyl group or a phenyl group.

10. The electrophotographic photosensitive member according to claim 1 , wherein the nitrogen-containing h

Assignees

• Canon Kk

Inventors

• Watariguchi Kaname
• Tanaka Masato

Classifications

• G03G5/0521

  comprising one or more heterocyclic groups · CPC title

• G03G5/0589

  Macromolecular compounds characterised by specific side-chain substituents or end groups · CPC title

• G03G5/0696 Primary

  Phthalocyanines · CPC title

• G03G5/0542

  Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines · CPC title

• G03G5/0612

  containing nitrogen · CPC title