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

An electrophotographic apparatus comprising an electrophotographic photosensitive member and at least one unit selected from the group consisting of a charging unit, an exposing unit, a developing unit, a transfer unit and a cleaning unit, the electrophotographic photosensitive member comprising:

• a support;
• and
• a photosensitive layer on the support, wherein
• a surface layer of the electrophotographic photosensitive member contains a polymer of a hole transport compound having at least one monovalent polymerizable functional group, the hole transport compound being represented by Formula (1)
• where R1 and R2 independently represent a hydrogen atom, a fluorine atom, an alkyl group, a fluorine atom-substituted alkyl group, a phenyl group-substituted alkyl group, a phenyl group, an alkyl group-substituted phenyl group, an alkyl group having said monovalent polymerizable functional group as a substituent, a phenyl group-substituted alkyl group having said monovalent polymerizable functional group as a substituent, a phenyl group having said monovalent polymerizable functional group as a substituent, or an alkyl group-substituted phenyl group having said monovalent polymerizable functional group as a substituent, and at least one of R1 and R2 is a trifluoromethyl group,
• R3 and R4 independently represent a hydrogen atom, an alkyl group, an alkoxy group, a phenyl group, an alkyl group having said monovalent polymerizable functional group as a substituent, an alkoxy group having said monovalent polymerizable functional group as a substituent, or a phenyl group having said monovalent polymerizable functional group as a substituent,
• Ar1 and Ar2 independently represent a single bond, an arylene group, or an alkyl group-substituted arylene group,
• n represents an integer of 1 to 5,
• when n is 2 or more, structures in parentheses may be the same or different from each other,
• Z1 represents a monovalent group represented by Formula (2), and
• Z2 represents a hydrogen atom or the monovalent group represented by Formula (2), with the proviso that when Z2 is represented by Formula (2), Z1 and Z2 may be the same or different from each other,
• where * represents a bonding position at which Ar1 or Ar2 is bonded, and
• Ar11 and Ar12 independently represent an aryl group, an alkyl group-substituted aryl group, an alkoxy group-substituted aryl group, an aryl group having said monovalent polymerizable functional group as a substituent, an alkyl group-substituted aryl group having said monovalent polymerizable functional group as a substituent, or an alkoxy group-substituted aryl group having said monovalent polymerizable functional group as a substituent;
• and
• said monovalent polymerizable functional group is represented by Formula (3)
• where ** represents a bonding position at which R1 to R4, Ar11 and Ar12 are bonded,
• R11 represents a single bond or an alkylene group having 6 or less carbon atoms,
• R12 represents a hydrogen atom or a methyl group, and
• s is 0 or 1,
• with the proviso that when s is 1, R11 is not a single bond, and
• with the proviso that when the number of groups having a monovalent polymerizable functional group is 2 or more, their structures may be the same or different from each other.

A process cartridge comprising an electrophotographic photosensitive member and at least one unit that is integrally supported, the at least one unit being selected from the group consisting of a charging unit, a developing unit and a cleaning unit, the process cartridge being detachably attachable to an electrophotographic apparatus main body, the electrophotographic photosensitive member comprising:

• a support;
• and
• a photosensitive layer on the support, wherein
• a surface layer of the electrophotographic photosensitive member contains a polymer of a hole transport compound having at least one monovalent polymerizable functional group, the hole transport compound being represented by Formula (1)
• where R1 and R2 independently represent a hydrogen atom, a fluorine atom, an alkyl group, a fluorine atom-substituted alkyl group, a phenyl group-substituted alkyl group, a phenyl group, an alkyl group-substituted phenyl group, an alkyl group having said monovalent polymerizable functional group as a substituent, a phenyl group-substituted alkyl group having said monovalent polymerizable functional group as a substituent, a phenyl group having said monovalent polymerizable functional group as a substituent, or an alkyl group-substituted phenyl group having said monovalent polymerizable functional group as a substituent, and at least one of R1 and R2 is a trifluoromethyl group,
• R3 and R4 independently represent a hydrogen atom, an alkyl group, an alkoxy group, a phenyl group, an alkyl group having said monovalent polymerizable functional group as a substituent, an alkoxy group having said monovalent polymerizable functional group as a substituent, or a phenyl group having said monovalent polymerizable functional group as a substituent,
• Ar1 and Ar2 independently represent a single bond, an arylene group, or an alkyl group-substituted arylene group,
• n represents an integer of 1 to 5,
• when n is 2 or more, structures in parentheses may be the same or different from each other,
• Z1 represents a monovalent group represented by Formula (2), and
• Z2 represents a hydrogen atom or the monovalent group represented by Formula (2), with the proviso that when Z2 is represented by Formula (2), Z1 and Z2 may be the same or different from each other,
• where * represents a bonding position at which Ar1 or Ar2 is bonded, and
• Ar11 and Ar12 independently represent an aryl group, an alkyl group-substituted aryl group, an alkoxy group-substituted aryl group, an aryl group having said monovalent polymerizable functional group as a substituent, an alkyl group-substituted aryl group having said monovalent polymerizable functional group as a substituent, or an alkoxy group-substituted aryl group having said monovalent polymerizable functional group as a substituent;
• and
• said monovalent polymerizable functional group is represented by Formula (3)
• where ** represents a bonding position at which R1 to R4, Ar11 and Ar12 are bonded,
• R11 represents a single bond or an alkylene group having 6 or less carbon atoms,
• R12 represents a hydrogen atom or a methyl group, and
• s is 0 or 1,
• with the proviso that when s is 1, R11 is not a single bond, and
• with the proviso that when the number of groups having a monovalent polymerizable functional group is 2 or more, their structures may be the same or different from each other.