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

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 polymer of a composition comprising:

a compound represented by the following formula (1);

a compound represented by the following formula (2); and

a compound represented by the following formula (5), and

a crosslinking agent having a group capable of being bonded to one of a hydroxy group or a carboxyl group:

in the formulae (1), (2), and (5), R 1 and R 2 are not identical to each other, and are each represented by the following formula (10), and

in the formulae (1), (2), and (5), each X is identical, and each X represents a tetravalent structures represented by the following formula (X1):

in the formula (10), R a represents a branched or linear alkylene group having 1 or more and 10 or less carbon atoms that optionally has a substituent, or a phenylene group that optionally has a substituent,

in the formula (10), R b represents —O—, —S—, or a group represented by the following formula (11):

in the formula (11), R d represents a hydrogen atom, or a branched or linear alkyl group having 1 or more and 4 or less carbon atoms, and

in the formula (10), R c represents a hydrogen atom, a branched or linear alkyl group having 1 or more and 10 or less carbon atoms that optionally has a substituent, an aryl group having 6 or more and 14 or less carbon atoms that optionally has a substituent, or a branched or linear arylalkyl group having 7 or more and 18 or less carbon atoms that optionally has a substituent,

in a case that the alkylene group or the alkyl group has a substituent, the substituent is a hydroxy group, a carboxyl group, an amino group, a thiol group, an alkoxy group having 1 or more and 3 or less carbon atoms, or an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms,

in a case that the phenylene group, the aryl group, or the arylalkyl group has a substituent, the substituent is an alkyl group having 1 or more and 3 or less carbon atoms, a hydroxy group, a hydroxyalkyl group having 1 or more and 3 or less carbon atoms, a carboxyl group, an amino group, a thiol group, an alkoxy group having 1 or more and 3 or less carbon atoms, an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms, a halogen atom, a cyano group, or a nitro group,

m represents 0 or 1, and n represents 0 or l, and

R 1 contains a hydroxy group or a carboxyl group, and

R 2 contains a hydroxy group or a carboxyl group:

in the formula (X1), R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, or a nitro group.

2 . The electrophotographic photosensitive member according to claim 1 , wherein in each of the formulae (1), (2), and (5), at least one selected from the group consisting of R 1 and R 2 represents a group represented by the following formula (7):

in the formula (7), R 5 and R 6 each independently represent a group selected from the group consisting of: a branched or linear alkyl group having 1 or more and 7 or less carbon atoms that optionally has a substituent; a benzyl group; an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms; and a phenyl group, and in a case that the alkyl group has a substituent, the substituent is a group selected from the group consisting of: an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms; a phenyl group; a phenol group; a hydroxy group; a thiol group; an amino group; and a carboxyl group.

3 . The electrophotographic photosensitive member according to claim 1 , wherein in the composition, a mass ratio of the compound represented by the formula (1) to the compound represented by the formula (2) is 0.25 or more and 4 or less.

4 . A process cartridge comprising:

the electrophotographic photosensitive member of claim 1 ; and

at least one unit selected from the group consisting of:

a charging unit;

a developing unit; and

a cleaning unit,

the process cartridge integrally supporting the electrophotographic photosensitive member and the at least one unit, and being detachably attachable to a main body of an electrophotographic apparatus.

5 . An electrophotographic apparatus comprising:

the electrophotographic photosensitive member of claim 1 ;

a charging unit;

an exposing unit;

a developing unit; and

a transferring unit.

6 . A method of producing an electrophotographic photosensitive member comprising:

a support,

an undercoat layer formed on the support, and

a photosensitive layer formed on the undercoat layer, the method comprising:

forming a coating film of a coating liquid for an undercoat layer comprising:

a compound represented by the formula (1),

a compound represented by the formula (2), and

a crosslinking agent having a group capable of being bonded to one of a hydroxy group or a carboxyl group; and

polymerizing the coating film to form the undercoat layer:

in the formulae (1), (2), and (5), R 1 and R 2 are not identical to each other, and are each represented by the following formula (10), and

in the formulae (1), (2), and (5), each X is identical, and each X represents a tetravalent structures represented by the following formula (X1):

in the formula (10), R a represents a branched or linear alkylene group having 1 or more and 10 or less carbon atoms that optionally has a substituent, or a phenylene group that optionally has a substituent,

in the formula (10), R b represents —O—, —S—, or a group represented by the following formula (11):

in the formula (11), R d represents a hydrogen atom, or a branched or linear alkyl group having 1 or more and 4 or less carbon atoms, and

in the formula (10), R c represents a hydrogen atom, a branched or linear alkyl group having 1 or more and 10 or less carbon atoms that may have a substituent, an aryl group having 6 or more and 14 or less carbon atoms that optionally has a substituent, or a branched or linear arylalkyl group having 7 or more and 18 or less carbon atoms that optionally has a substituent,

in a case that the alkylene group or the alkyl group has a substituent, the substituent is a hydroxy group, a carboxyl group, an amino group, a thiol group, an alkoxy group having 1 or more and 3 or less carbon atoms, or an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms,

in a case that the phenylene group, the aryl group, or the arylalkyl group has a substituent, the substituent is an alkyl group having 1 or more and 3 or less carbon atoms, a hydroxy group, a hydroxyalkyl group having 1 or more and 3 or less carbon atoms, a carboxyl group, an amino group, a thiol group, an alkoxy group having 1 or more and 3 or less carbon atoms, an alkoxycarbonyl group having 2 or more and 4 or less carbon atoms, a halogen atom, a cyano group, or a nitro group,

m represents 0 or 1, and n represents 0 or l, and

R 1 contains a hydroxy group or a carboxyl group, and

R 2 contains a hydroxy group or a carboxyl group:

in the formulae (X1), R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, or a nitro group.