Electrophotographic photosensitive member, electrophotographic apparatus, and process cartridge

An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging unit, an exposure unit, a developing unit, and a transfer unit,

• wherein the electrophotographic photosensitive member comprises a support member and a photosensitive layer on the support member,
• wherein a surface layer of the electrophotographic photosensitive member contains a polymer of a hole transporting compound represented by the following Formula (1),
• (where in Formula (1), Ar1 is a substituted or unsubstituted aryl group;
• Ar2 and Ar3 are each independently a substituted or unsubstituted arylene group;
• Ar1 to Ar3 do not have a fluorine atom;
• substituents of the aryl group or arylene groups of Ar1 to Ar3 are groups selected from the group consisting of a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a monovalent group having a polymerizable functional group, and at least one of the aryl group or arylene groups of Ar1 to Ar3 has the monovalent group having the polymerizable functional group;
• Z1 is a monovalent group represented by the following Formula (2) or a monovalent group represented by the following Formula (3);
• Z2 is a hydrogen atom, a monovalent group represented by the following Formula (2), or a monovalent group represented by the following Formula (3);
• when Z1 and Z2 are the monovalent groups represented by the following Formula (2), or Z1 and Z2 are the monovalent groups represented by the following Formula (3), structures of Z1 and Z2 are equal to or different from each other),
• (in Formula (2), * is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R21 and R22 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• p is 0 or 1;
• q is an integer of 1 or more and 4 or less;
• r is 0 or 1;
• p, q, and r satisfy 2≤p+q+r≤4;
• when q is 2 or more, (R21)s are groups equal to or different from each other, and (R22)s are groups equal to or different from each other;
• Ar21 is a (s+1) valent group derived by removing (s+1) hydrogen atoms from substituted or unsubstituted arene;
• R23 is a fluorine atom, a C1 or C2 alkyl group having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
• s is the number of (R23)s directly bonded to Ar21, and is an integer of 1 or more and 5 or less;
• when s is 2 or more, (R23)s are groups equal to or different from each other),
• (in Formula (3), ** is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R31 and R32 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• t is an integer of 1 or more and 3 or less;
• when t is 2 or more, (R31)s are groups equal to or different from each other, and (R32)s are groups equal to or different from each other;
• Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
• R33 is a fluorine atom, a (C1-C4) alkyl group having a fluorine atom as a substituent, or a (C1-C3) alkoxy group having a fluorine atom as a substituent;
• u is the number of (R33)s directly bonded to Ar31, and is an integer of 1 or more and 5 or less;
• and when u is 2 or more, (R33)s are groups equal to or different from each other).

A process cartridge integrally supporting an electrophotographic photosensitive member and at least one unit selected from a charging unit, a developing unit, and a cleaning unit, and being attachable to and detachable from a main body of an electrophotographic apparatus,

• wherein the electrophotographic photosensitive member comprises a support member and a photosensitive layer on the support member,
• wherein a surface layer of the electrophotographic photosensitive member contains a polymer of a hole transporting compound represented by the following Formula (1),
• (where in Formula (1), Ar1 is a substituted or unsubstituted aryl group;
• Ar2 and Ar3 are each independently a substituted or unsubstituted arylene group;
• Ar1 to Ar3 do not have a fluorine atom;
• substituents of the aryl group or arylene groups of Ar1 to Ar3 are groups selected from the group consisting of a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a monovalent group having a polymerizable functional group, and at least one of the aryl group or arylene groups of Ar1 to Ar3 has the monovalent group having the polymerizable functional group;
• Z1 is a monovalent group represented by the following Formula (2) or a monovalent group represented by the following Formula (3);
• Z2 is a hydrogen atom, a monovalent group represented by the following Formula (2), or a monovalent group represented by the following Formula (3);
• when Z1 and Z2 are the monovalent groups represented by the following Formula (2), or Z1 and Z2 are the monovalent groups represented by the following Formula (3), structures of Z1 and Z2 are equal to or different from each other),
• (in Formula (2), * is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R21 and R22 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• p is 0 or 1;
• q is an integer of 1 or more and 4 or less;
• r is 0 or 1;
• p, q, and r satisfy 2≤p+q+r≤4;
• when q is 2 or more, (R21)s are groups equal to or different from each other, and (R22)s are groups equal to or different from each other;
• Ar21 is a (s+1) valent group derived by removing (s+1) hydrogen atoms from substituted or unsubstituted arene;
• R23 is a fluorine atom, a C1 or C2 alkyl group having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
• s is the number of (R23)s directly bonded to Ar21, and is an integer of 1 or more and 5 or less;
• when s is 2 or more, (R23)s are groups equal to or different from each other),
• (in Formula (3), ** is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R31 and R32 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• t is an integer of 1 or more and 3 or less;
• when t is 2 or more, (R31)s are groups equal to or different from each other, and (R32)s are groups equal to or different from each other;
• Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
• R33 is a fluorine atom, a (C1-C4) alkyl group having a fluorine atom as a substituent, or a (C1-C3) alkoxy group having a fluorine atom as a substituent;
• u is the number of (R33)s directly bonded to Ar31, and is an integer of 1 or more and 5 or less;
• and when u is 2 or more, (R33)s are groups equal to or different from each other).

A manufacturing method of an electrophotographic photosensitive member having a support member and a photosensitive layer on the support member, wherein

• the manufacturing method comprising a process of forming a coating film of a surface layer coating solution containing a hole transporting compound represented by the following Formula (1), a process of polymerizing the hole transporting compound represented by the following Formula (1) in the coating film of the surface layer coating solution, and a process of forming a surface layer of the electrophotographic photosensitive member,
• (where in Formula (1), Ar1 is a substituted or unsubstituted aryl group;
• Ar2 and Ar3 are each independently a substituted or unsubstituted arylene group;
• Ar1 to Ar3 do not have a fluorine atom;
• substituents of the aryl group or arylene groups of Ar1 to Ar3 are groups selected from the group consisting of a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a monovalent group having a polymerizable functional group, and at least one of the aryl group or arylene groups of Ar1 to Ar3 has the monovalent group having the polymerizable functional group;
• Z1 is a monovalent group represented by the following Formula (2) or a monovalent group represented by the following Formula (3);
• Z2 is a hydrogen atom, a monovalent group represented by the following Formula (2), or a monovalent group represented by the following Formula (3);
• when Z1 and Z2 are the monovalent groups represented by the following Formula (2), or Z1 and Z2 are the monovalent groups represented by the following Formula (3), structures of Z1 and Z2 are equal to or different from each other),
• (in Formula (2), * is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R21 and R22 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• p is 0 or 1;
• q is an integer of 1 or more and 4 or less;
• r is 0 or 1;
• p, q, and r satisfy 2≤p+q+r≤4;
• when q is 2 or more, (R21)s are groups equal to or different from each other, and (R22)s are groups equal to or different from each other;
• Ar21 is a (s+1) valent group derived by removing (s+1) hydrogen atoms from substituted or unsubstituted arene;
• R23 is a fluorine atom, a C1 or C2 alkyl group having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
• s is the number of (R23)s directly bonded to Ar21, and is an integer of 1 or more and 5 or less;
• when s is 2 or more, (R23)S are groups equal to or different from each other),
• (in Formula (3), ** is a bonding position of the substituent bonded to Ar2 or Ar3 in Formula (1);
• R31 and R32 are each independently a hydrogen atom or a (C1-C4) alkyl group;
• t is an integer of 1 or more and 3 or less;
• when t is 2 or more, (R31)s are groups equal to or different from each other, and (R32)s are groups equal to or different from each other;
• Ar31 is a (u+1) valent arene derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
• R33 is a fluorine atom, a (C1-C4) alkyl group having a fluorine atom as a substituent, or a (C1-C3) alkoxy group having a fluorine atom as a substituent;
• u is the number of (R33)s directly bonded to Ar31, and is an integer of 1 or more and 5 or less;
• and when u is 2 or more, (R33)S are groups equal to or different from each other).