Electrophotographic photosensitive member, method for producing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

Patent metadata

Field	Value
Publication number	US-9316932-B2
Application number	US-201314082642-A
Country	US
Kind code	B2
Filing date	Nov 18, 2013
Priority date	Nov 19, 2012
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

An electrophotographic photosensitive member includes a support and a photosensitive layer formed on the support. A surface layer of the electrophotographic photosensitive member contains a polymerized product of a composition that contains a charge transporting compound having a particular group (chain polymerizable functional group).

First claim

What is claimed is:

1. An electrophotographic photosensitive member comprising:
a support, and
a photosensitive layer formed on the support,
wherein a surface layer of the electrophotographic photosensitive member comprises a polymerized product of a composition comprising a charge transporting compound with a polymerizable functional group represented by formula (1) below,

where,
R 1 and R 2 each independently represent a hydrogen atom or a straight alkyl group, and
at least one of R 1 and R 2 is the straight alkyl group, and
wherein the charge transporting compound is a compound represented by formula (3) or (4) below,

where,
Ar 1 , Ar 2 , and Ar 4 each independently represent a monovalent group represented by formula (M1) below or a substituted or unsubstituted aryl group;
Ar 3 represents a divalent group represented by formula (M2) below or a substituted or unsubstituted arylene group; at least one of Ar 1 to Ar 4 represents a monovalent group represented by formula (M1) below or a divalent group represented by formula (M2) below; r is 0 or 1; and when none of Ar 1 , Ar 2 , and Ar 4 is a monovalent group represented by formula (M1) below, r is 1 and Ar 3 is a divalent group represented by formula (M2) below;

where,
A 5 , Ar 6 , Ar 9 , and Ar 10 each independently represent a monovalent group represented by formula (M1) below or a substituted or unsubstituted aryl group; Ar 7 and Ar 8 each independently represent a divalent group represented by formula (M2) below or a substituted or unsubstituted arylene group; at least one of A 5 to Ar 8 is a monovalent group represented by formula (M1) below or a divalent group represented by formula (M2) below; P 1 represents an oxygen atom, a cycloalkylidene group, a divalent group having two phenylene groups bonded through an oxygen atom, or an ethylene group; s and t each independently represent 0 or 1; and when none of A 5 , Ar 6 , Ar 9 , and Ar 10 is a monovalent group represented by formula (M1) below and Ar 7 is not a divalent group represented by formula (M2) below, t is 1 and Ar 8 is a divalent group represented by formula (M2) below;

where,
R 1 and R 2 are the same as R 1 and R 2 in formula (1), Ar 11 represents a substituted or unsubstituted arylene group, and m represents an integer of 1 or more:

where,
R 1 and R 2 are the same as R 1 and R 2 in formula (1), Ar 12 represents a substituted or unsubstituted trivalent aromatic hydrocarbon group, and n represents an integer of 1 or more.

2. The electrophotographic photosensitive member according to claim 1 , wherein the charge transporting compound is a charge transporting compound with a polymerizable functional group represented by formula (2) below,

where,
R 1 and R 2 are the same as R 1 and R 2 in formula (1).

3. The electrophotographic photosensitive member according to claim 2 , wherein R 1 and R 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, or a n-propyl group, and at least one of R 1 and R 2 is the methyl group, the ethyl group, or the n-propyl group.

4. The electrophotographic photosensitive member according to claim 3 , wherein R 1 is a hydrogen atom and R 2 is a methyl group, an ethyl group, or a n-propyl group.

5. The electrophotographic photosensitive member according to claim 4 , wherein R 1 is a hydrogen atom and R 2 is a methyl group.

6. The electrophotographic photosensitive member according to claim 1 , wherein the charge transporting compound is a compound represented by formula (3) and at least two of Ar 1 to Ar 4 are each a monovalent group represented by formula (M1) or a divalent group represented by formula (M2).

7. The electrophotographic photosensitive member according to claim 1 , wherein the charge transporting compound is a compound represented by formula (4) and at least two of Ar 5 to Ar 10 are each a monovalent group represented by formula (M1) or a divalent group represented by formula (M2).

8. The electrophotographic photosensitive member according to claim 1 , wherein the composition further comprises at least one compound selected from the group consisting of a compound represented by formula (B) below and a compound represented by formula (C) below,

where,
X 1 and X 2 each independently represent a methyl group, an ethyl group, a n-propyl group, a methoxymethyl group, a trifluoromethyl group, a trichloromethyl group, a methoxy group, an ethoxy group, a propoxy group, a methoxymethoxy group, a trifluoromethoxy group, a trichloromethoxy group, a dimethylamino group, or a fluorine atom; Y 1 and Y 2 each independently represent an alkylene group; Z 1 to Z 4 each independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a monovalent group represented by formula (5) below, or a monovalent group represented by formula (6) below; at least one of Z 1 to Z 4 represents an acryloyloxy group, a methacryloyloxy group, a monovalent group represented by formula (5) below, or a monovalent group represented by formula (6) below; a and b each independently represent an integer of 0 or more and 5 or less; and c and d each independently represent 0 or 1,

where,
X 11 to X 13 each independently represent a methyl group, an ethyl group, a n-propyl group, a methoxymethyl group, a trifluoromethyl group, a trichloromethyl group, a methoxy group, an ethoxy group, a propoxy group, a methoxymethoxy group, a trifluoromethoxy group, a trichloromethoxy group, a dimethylamino group, or a fluorine atom; Y 11 to Y 16 each independently represent an alkylene group; Z 11 to Z 16 each independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a monovalent group represented by formula (5) below, or a monovalent group represented by formula (6) below; at least one of Z 11 to Z 16 is an acryloyloxy group, a methacryloyloxy group, a monovalent group represented by formula (5) below, or a monovalent group represented by formula (6) below; g and h each independently represent an integer of 0 or more and 5 or less; i represents an integer of 0 or more and 4 or less; and j and k each independently represent 0 or 1;

9. A method for producing the electrophotographic photosensitive member according to claim 1 , the method comprising:
forming a coat by using a surface layer-forming coating solution comprising a composition comprising the charge transporting compound; and
forming a surface layer by polymerizing the composition contained in the coat.

10. The method according to claim 9 , wherein the composition is polymerized by irradiating the coat with an electron beam.

11. A process cartridge detachably attachable to a main body of an electrophotographic apparatus, wherei

Assignees

• Canon Kk

Inventors

• Nonaka Masaki
• Nagasaka Hideaki
• Tanaka Masato

Classifications

• G03G5/0668

  containing only one methine or polymethine group · CPC title

• G03G5/076

  having a photoconductive moiety in the polymer backbone · CPC title

• G03G5/0666

  containing a methine or polymethine group · CPC title

• G03G5/0618 Primary

  containing oxygen and nitrogen · CPC title

• G03G5/0672

  containing two or more methine or polymethine groups · CPC title