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

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, wherein the process cartridge integrally supports: the electrophotographic photosensitive member according to claim 1 , and at least one unit selected from the group consisting of a charging unit, a development unit, a transfer unit, and a cleaning unit.

12. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to claim 1 , a charging unit, an exposure unit, a development unit, and a transfer unit.