Electrophotographic photosensitive member, process cartridge, electrophotographic apparatus, and imide compound

Patent metadata

Field	Value
Publication number	US-9442401-B2
Application number	US-201414564969-A
Country	US
Kind code	B2
Filing date	Dec 9, 2014
Priority date	Dec 26, 2013
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

An electrophotographic photosensitive member including: a support; an undercoat layer formed on the support; and a photosensitive layer formed on the undercoat layer. The undercoat layer contains a polymerized product of a composition containing a compound represented by formula (1).

First claim

What is claimed is:

1. An electrophotographic photosensitive member comprising:
a support;
an undercoat layer formed on the support; and
a photosensitive layer formed on the undercoat layer;
wherein the undercoat layer comprises a polymerized product of a composition comprising an imide compound represented by the following formula (1),

wherein
R 1 to R 4 each independently represent a hydrogen atom, a cyano group, a nitro group, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
R 5 to R 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, or a substituted or unsubstituted alkyl group,
A 1 represents a hydroxy group, a thiol group, an amino group, or a carboxy group,
R 9 represents an unsubstituted or substituted alkylene group where the distance to A 1 is 2 to 6 atoms, a group where the distance to A 1 is 2 to 6 atoms, which is derived from substitution of CONH for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, or a group where the distance to A 1 is 2 to 6 atoms, which is derived from substitution of NR 11 for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a substituent of the substituted alkylene group is an alkyl group having 1 to 4 carbon atoms,
R 11 represents an alkyl group,
R 10 represents a group represented by —R 12 -A 2 ,
A 2 represents a hydroxy group, a thiol group, an amino group, or a carboxy group,
R 12 represents an unsubstituted or substituted alkylene group where the distance to A 2 is 2 to 12 atoms, a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of an oxygen atom for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of a sulfur atom for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, or a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of NR 13 for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a substituent of the substituted alkylene group is an alkyl group having 1 to 6 carbon atoms, a phenyl group, a benzyl group, or an alkoxycarbonyl group, and
R 13 represents a hydrogen atom, or an alkyl group.

2. The electrophotographic photosensitive member according to claim 1 , wherein R 9 of the formula (1) represents an ethylene group, a propylene group or a butylene group.

3. The electrophotographic photosensitive member according to claim 1 , wherein R 12 of the formula (1) represents a substituted alkylene group where the distance to A 2 is 2 to 12 atoms.

4. The electrophotographic photosensitive member according to claim 1 , wherein A 1 and A 2 represent hydroxy groups.

5. The electrophotographic photosensitive member according to claim 1 , wherein the composition comprising the compound represented by the formula (1) further comprises a crosslinking agent.

6. The electrophotographic photosensitive member according to claim 5 , wherein the composition further comprises a resin having a polymerizable functional group.

7. The electrophotographic photosensitive member according to claim 6 , wherein the polymerizable functional group of the resin is a hydroxy group, a thiol group, an amino group, a carboxy group or a methoxy group.

8. The electrophotographic photosensitive member according to claim 5 , wherein the crosslinking agent is:
an isocyanate compound having an isocyanate group or a blocked isocyanate group; or
an amine compound having an N-methylol group or an alkyl-etherified N-methylol group.

9. The electrophotographic photosensitive member according to claim 5 , wherein the mass ratio of the crosslinking agent to the compound represented by the formula (1) is in the range of 100:50 to 100:250.

10. A process cartridge detachably attachable to a main body of an electrophotographic apparatus, wherein the process cartridge integrally supports: the electrophotographic photosensitive member according to claim 1 ; and at least one device selected from the group consisting of a charging device, a developing device and a cleaning device.

11. An electrophotographic apparatus having the electrophotographic photosensitive member according to claim 1 , a charging device, an image exposure device, a developing device and a transfer device.

12. An imide compound represented by formula (1),

wherein
R 1 to R 4 each independently represent a hydrogen atom, a cyano group, a nitro group, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
R 5 to R 8 each independently represent a hydrogen atom, a halogen atom, a nitro group, or a substituted or unsubstituted alkyl group,
A 1 represents a hydroxy group, a thiol group, an amino group, or a carboxy group,
R 9 represents an unsubstituted or substituted alkylene group where the distance to A 1 is 2 to 6 atoms, a group where the distance to A 1 is 2 to 6 atoms, which is derived from substitution of CONH for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, or a group where the distance to A 1 is 2 to 6 atoms, which is derived from substitution of NR 11 for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a substituent of the substituted alkylene group is an alkyl group having 1 to 4 carbon atoms,
R 11 represents an alkyl group,
R 10 represents a group represented by —R 12 -A 2 ,
A 2 represents a hydroxy group, a thiol group, an amino group, or a carboxy group,
R 12 represents an unsubstituted or substituted alkylene group where the distance to A 2 is 2 to 12 atoms, a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of an oxygen atom for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of a sulfur atom for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, or a group where the distance to A 2 is 2 to 12 atoms, which is derived from substitution of NR 13 for one of the CH 2 's in the main chain of an unsubstituted or substituted alkylene group, a substituent of the substituted alkylene group is an alkyl group having 1 to 6 carbon atoms, a phenyl group, a benzyl group, or an alkoxycarbonyl group, and
R 13 represents a hydrogen atom, or an alkyl group.

Assignees

• Canon Kk

Inventors

• Sekido Kunihiko
• Nishi Masashi
• Tagami Kei

Classifications

• G03G5/14 Primary

  Inert intermediate or cover layers for charge-receiving layers (for photoconductive, charge-generation or charge-transporting layers G03G5/04) · CPC title

• G03G5/0651

  containing four relevant rings · CPC title

• G03G5/142

  Inert intermediate layers · CPC title