Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

Patent metadata

Field	Value
Publication number	US-2016131985-A1
Application number	US-201514928769-A
Country	US
Kind code	A1
Filing date	Oct 30, 2015
Priority date	Nov 11, 2014
Publication date	May 12, 2016
Grant date	—

Abstract

Provided is an electrophotographic photosensitive member, including in the following order: a support; a charge-generating layer; and a charge-transporting layer, in which: the charge-generating layer includes a gallium phthalocyanine crystal in which an organic compound is contained; the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone; a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4).

First claim

What is claimed is:

1 . An electrophotographic photosensitive member, comprising in the following order:
a support; a charge-generating layer; and a charge-transporting layer, wherein: the charge-generating layer comprises a gallium phthalocyanine crystal in which an organic compound is contained; the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone; a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4):

in the formula (1):
Ar 1 and Ar 2 each independently represent a substituted or unsubstituted phenyl group;
X represents a phenylene group;
Y 1 and Y 2 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, or a group represented by the following formula (A);
a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; and
a substituent of the substituted benzyl group is a methyl group or an ethyl group,

in the formula (A):
Ar 3 represents a substituted or unsubstituted phenyl group;
a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group;
R 1 represents a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; and
a substituent of the substituted alkyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group,

in the formula (2):
Ar 101 to Ar 104 each independently represent a substituted or unsubstituted aryl group,

in the formula (3):
Ar 105 to Ar 110 each independently represent a substituted or unsubstituted aryl group; and
Ar 111 represents a phenylene group or a 4,4′-biphenyldiyl group,

in the formula (4):
Ar 112 to Ar 117 each independently represent a substituted or unsubstituted aryl group;
Ar 118 and Ar 119 each independently represent a phenylene group or a 4,4′-biphenyldiyl group; and
R 101 and R 102 each independently represent an alkyl group or a phenyl group, or R 101 and R 102 represent groups necessary for forming a ring structure by being bonded to each other together with a carbon atom to which R 101 and R 102 are bonded.

2 . An electrophotographic photosensitive member according to claim 1 , wherein a content of the organic compound is 0.4% by mass or more and 1.4% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal.

3 . An electrophotographic photosensitive member according to claim 1 , wherein the organic compound is at least one compound selected from the group consisting of N-methylformamide, N-propylformamide, and N-vinylformamide.

4 . An electrophotographic photosensitive member according to claim 1 , wherein Y 1 in the formula (1) represents a 9,9-dimethyl-9H-fluoren-2-yl group.

5 . An electrophotographic photosensitive member according to claim 4 , wherein Y 1 and Y 2 in the formula (1) each represent a 9,9-dimethyl-9H-fluoren-2-yl group.

6 . An electrophotographic photosensitive member according to claim 1 , wherein Ar 1 and Ar 2 in the formula (1) each represent a tolyl group.

7 . An electrophotographic photosensitive member according to claim 1 , wherein at least one of Ar 101 to Ar 104 , at least one of Ar 105 to Ar 110 , and at least one of Ar 112 to Ar 117 in the formulae (2) to (4) each represent a 9,9-dimethyl-9H-fluoren-2-yl group.

8 . An electrophotographic photosensitive member according to claim 7 , wherein Ar 105 and Ar 106 in the formula (3) each represent a 9,9-dimethyl-9H-fluoren-2-yl group.

9 . An electrophotographic photosensitive member according to claim 7 , wherein Ar 112 and Ar 113 in the formula (4) each represent a 9,9-dimethyl-9H-fluoren-2-yl group and R 101 and R 102 in the formula (4) each represent a methyl group.

10 . An electrophotographic photosensitive member according to claim 1 , wherein the gallium phthalocyanine crystal is a hydroxygallium phthalocyanine crystal.

11 . An electrophotographic photosensitive member according to claim 1 , wherein the gallium phthalocyanine crystal is a chlorogallium phthalocyanine crystal.

12 . A process cartridge, which integrally supports an electrophotographic photosensitive member and at least one device selected from the group consisting of a charging device, a developing device, a transferring device and a cleaning device, and is detachably mountable to a main body of an electrophotographic apparatus, wherein:
the electrophotographic photosensitive member comprises in the following order:
a support;
a charge-generating layer; and
a charge-transporting layer,
the charge-generating layer comprises a gallium phthalocyanine crystal in which an organic compound is contained; the organic compound is at least one compound selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N-methylformamide, N-propylformamide, N-vinylformamide, and N-methylpyrrolidone; a content of the organic compound is 0.1% by mass or more and 1.5% by mass or less with respect to a mass of gallium phthalocyanine in the gallium phthalocyanine crystal; and the charge-transporting layer comprises at least one compound selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2), a compound represented by the formula (3), and a compound represented by the formula (4):

in the formula (1):
Ar 1 and Ar 2 each independently represent a substituted or unsubstituted phenyl group;
X represents a phenylene group;
Y 1 and Y 2 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, or a group represented by the following formula (A);
a substituent of the substituted phenyl group is an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, or a phenyl group; and
a substituent of the substituted benzyl group is a methyl group or an ethyl group,

in the formula (A):
Ar 3 represents a substituted or unsubstituted phenyl group;
a substituent of the substi

Assignees

• Canon Kk

Inventors

• Tanaka Masato
• Kawahara Masataka
• Nishida Tsutomu

Classifications

• G03G5/0436 Primary

  combining organic and inorganic layers · CPC title

• G03G5/0696

  Phthalocyanines · CPC title

• G03G5/0614

  Amines · CPC title

• G03G5/06147

  alkenylarylamine · CPC title

• G03G5/061443

  benzidine · CPC title