Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

A method of producing an electrophotographic photosensitive member comprising a support, an electron-transporting layer, a charge-generating layer, and a hole-transporting layer in the stated order, the method comprising a step of forming a coating film of a coating liquid for an electron-transporting layer, followed by drying and/or curing of the coating film to form the electron-transporting layer,

• wherein the coating liquid for an electron-transporting layer comprises a polymer having a structural unit represented by the following formula (1), the following formula (2), or the following formula (3), and
• wherein the polymer has a glass transition temperature Tg of −10 to 50° C.:
• in the formula (1),
• R11, R12, R13, R14, R15, R16, R17, and R18 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R61 represents a hydrogen atom, or a substituted or unsubstituted alkyl group, and
• m1 represents an integer of 2 to 16;
• in the formula (2),
• R22, R23, R24, R26, R27, and R28 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R62 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R41 and R42 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m2 represents an integer of 2 to 16;
• and
• in the formula (3),
• R31, R33, R34, R35, R37, and R38 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R63 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R51 and R52 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m3 represents an integer of 2 to 16.

A process cartridge comprising:

• an electrophotographic photosensitive member;
• 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,
• the electrophotographic photosensitive member comprising in this order:
• a support;
• an electron-transporting layer;
• a charge-generating layer;
• and
• a hole-transporting layer,
• wherein the electron-transporting layer comprises a polymer having a structural unit represented by the following formula (1), the following formula (2), or the following formula (3), and
• wherein the polymer has a glass transition temperature Tg of −10 to 50° C.:
• in the formula (1),
• R11, R12, R13, R14, R15, R16, R17, and R18 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R61 represents a hydrogen atom, or a substituted or unsubstituted alkyl group, and
• m1 represents an integer of 2 to 16;
• in the formula (2),
• R22, R23, R24, R26, R27, and R28 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R62 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R41 and R42 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m2 represents an integer of 2 to 16;
• and
• in the formula (3),
• R31, R33, R34, R35, R37, and R38 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R63 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R51 and R52 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m3 represents an integer of 2 to 16.

An electrophotographic apparatus comprising:

• an electrophotographic photosensitive member;
• a charging unit;
• an exposing unit;
• a developing unit;
• and
• a transfer unit,
• the electrophotographic photosensitive member comprising in this order:
• a support;
• an electron-transporting layer;
• a charge-generating layer;
• and
• a hole-transporting layer,
• wherein the electron-transporting layer comprises a polymer having a structural unit represented by the following formula (1), the following formula (2), or the following formula (3), and
• wherein the polymer has a glass transition temperature Tg of −10 to 50° C.:
• in the formula (1),
• R11, R12, R13, R14, R15, R16, R17, and R18 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R61 represents a hydrogen atom, or a substituted or unsubstituted alkyl group, and
• m1 represents an integer of 2 to 16;
• in the formula (2),
• R22, R23, R24, R26, R27, and R28 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R62 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R41 and R42 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m2 represents an integer of 2 to 16;
• and
• in the formula (3),
• R31, R33, R34, R35, R37, and R38 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted aryl group,
• R63 represents a hydrogen atom, or a substituted or unsubstituted alkyl group,
• R1 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
• m3 represents an integer of 2 to 16.