Electrophotographic photosensitive member, process cartridge, electrophotographic apparatus and phthalocyanine crystal

Patent metadata

Field	Value
Publication number	US-9442399-B2
Application number	US-201314101289-A
Country	US
Kind code	B2
Filing date	Dec 9, 2013
Priority date	Dec 14, 2012
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

The photosensitive layer of an electrophotographic photosensitive member contains a phthalocyanine crystal in which a compound represented by the following formula ( 1 ) is contained:

First claim

What is claimed is:

1. An electrophotographic photosensitive member comprising
a support; and
a photosensitive layer formed on the support;
wherein the photosensitive layer comprises:
a phthalocyanine crystal in which a compound represented by the following formula (1) is contained:

wherein
the content of the compound represented by the formula (1) in the phthalocyanine crystal is 0.1% by mass or more and 3.0% by mass or less;
R 1 to R 4 each independently represent a hydrogen atom, a formyl group, an acetyl group, an alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and at least one of R 1 to R 4 is the substituted or unsubstituted aryl group, or the substituted or unsubstituted heterocyclic group;
the substituent of the substituted alkyl group is an alkoxy group, a morpholinoalkoxy group, a dialkylamino group, an alkoxycarbonyl group, a substituted or unsubstituted aryl group, an aryloxy group, a heterocyclic group, a halogen atom, a cyano group or a morpholino group;
the substituent of the substituted aryl group is a substituted or unsubstituted alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group; and
the substituent of the substituted heterocyclic group is an alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group,
provided that both of the R 1 and R 2 are not a hydrogen atom at the same time, and
provided that the substituent of the substituted aryl group is not an acetyl group or a benzoyl group.

2. The electrophotographic photosensitive member according to claim 1 , wherein the R 3 and R 4 are each a hydrogen atom.

3. The electrophotographic photosensitive member according to claim 1 , wherein the substituted or unsubstituted aryl group is a substituted or unsubstituted phenyl group, and
the substituent of the substituted phenyl group is a substituted or unsubstituted alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group.

4. The electrophotographic photosensitive member according to claim 3 , wherein the substituent of the substituted phenyl group is a halogen atom, a hydroxy group, a cyano group, a nitro group, a formyl group, an alkyl group or an alkoxy group.

5. The electrophotographic photosensitive member according to claim 1 , wherein the substituted or unsubstituted heterocyclic group is a substituted or unsubstituted pyridyl group, and
the substituent of the substituted pyridyl group is an alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group.

6. The electrophotographic photosensitive member according to claim 5 , wherein the substituent of the substituted or unsubstituted pyridyl group is a halogen atom, a hydroxy group, a cyano group, a nitro group, a formyl group, an alkyl group or an alkoxy group.

7. The electrophotographic photosensitive member according to claim 1 , wherein at least one of R 1 and R 2 is the substituted or unsubstituted alkyl group.

8. The electrophotographic photosensitive member according to claim 7 , wherein the substituent of the substituted alkyl group is a halogen atom, a dialkylamino group or a phenyl group.

9. The electrophotographic photosensitive member according to claim 7 , wherein the R 1 and R 2 are each independently a methyl group or an ethyl group.

10. A process cartridge detachably attachable to a main body of an electrophotographic apparatus, wherein the process cartridge integrally supports: an electrophotographic photosensitive member; and at least one device selected from the group consisting of a charging device, a developing device, a transfer device and a cleaning device,
wherein the electrophotographic photosensitive member comprises:
a support; and
a photosensitive layer formed on the support;
wherein the photosensitive layer comprises:
a phthalocyanine crystal in which a compound represented by the following formula (1) is contained

wherein
R 1 to R 4 each independently represent a hydrogen atom, a formyl group, an acetyl group, an alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and at least one of R 1 to R 4 is the substituted or unsubstituted aryl group, or the substituted or unsubstituted heterocyclic group;
the substituent of the substituted alkyl group is an alkoxy group, a morpholinoalkoxy group, a dialkylamino group, an alkoxycarbonyl group, a substituted or unsubstituted aryl group, an aryloxy group, a heterocyclic group, a halogen atom, a cyano group or a morpholino group;
the substituent of the substituted aryl group is a substituted or unsubstituted alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group; and
the substituent of the substituted heterocyclic group is an alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl group, a halogen atom, a hydroxy group, a nitro group, a cyano group, a formyl group or a morpholino group,
provided that both of the R 1 and R 2 are not a hydrogen atom at the same time, and
provided that the substituent of the substituted aryl group is not an acetyl group or a benzoyl group.

11. The process cartridge according to claim 10 , wherein the content of the compound represented by the formula (1) in the phthalocyanine crystal is 0.1% by mass or more and 3.0% by mass or less.

12. An electrophotographic apparatus comprising:
an electrophotographic photosensitive member with
a charging device, an image exposing device, a developing device and a transfer device,
wherein the electrophotographic photosensitive member comprises:
a support; and
a photosensitive layer formed on the support;
wherein the photosensitive layer comprises:
a phthalocyanine crystal in which a compound represented by the following formula (1is contained

wherein
R 1 to R 4 each independently represent a hydrogen atom, a formyl group, an acetyl group, an alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and wherein at least one of R 1 to R4 is the substituted or unsubstituted aryl group, or the substituted or unsubstituted heterocyclic group;
the substituent of the substituted alkyl group is an alkoxy group, a morpholinoalkoxy group, a dialkylamino group, an alkoxycarbonyl group, a substituted or unsubstituted aryl group, an aryloxy group, a heterocyclic group, a halogen atom, a cyano group or a morpholino group;
the sub stituent of the substituted aryl group is a substituted or unsubstituted alkyl group, an alkoxy group, a dialkylamino group, an alkoxycarbonyl grou

Assignees

• Canon Kk

Inventors

• Tanaka Masato

Classifications

• G03G5/0638 Primary

  containing two hetero atoms · CPC title

• G03G5/0614

  Amines · CPC title

• C09B47/04

  Phthalocyanines {abbreviation: Pc} · CPC title

• G03G5/047 Primary

  characterised by the charge-generation layers or charge transport layers {(G03G5/0433 and G03G5/0436 take precedence)} · CPC title

• G03G5/0696

  Phthalocyanines · CPC title