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US 10,310,395 B2Granted
Electrophotographic photosensitive member, electrophotographic apparatus, and process cartridge
AssigneeCanon Kabushiki Kaisha
InventorsKoichi Nakata, Haruki Mori, Shinji Takagi, Masaki Nonaka, Ryoichi Tokimitsu
Life of this patent
Estimating the term…
Abstract
Provided are an electrophotographic photosensitive member capable of satisfying abrasion resistance and electrical properties and suppressing image deletion, and an electrophotographic apparatus and a process cartridge having the electrophotographic photosensitive member. A surface layer of the electrophotographic photosensitive member contains a polymer of a hole transport material having a polymerizable functional group, wherein the hole transport material has a specific structure.
Claims17
An electrophotographic photosensitive member, comprising a support member bearing a photosensitive layer, said electrophotographic photosensitive member having a surface layer comprising a polymerization product of a hole transporting compound represented by Formula (1)
- where Ar1 is a substituted or unsubstituted aryl group;
- Ar2 and Ar3 are 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 selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, 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 Formula (2) or a monovalent group represented by Formula (3);
- Z2 is a hydrogen atom, a monovalent group represented by Formula (2), or a monovalent group represented by Formula (3);
- and when Z1 and Z2 are the monovalent groups represented by Formula (2), or when Z1 and Z2 are the monovalent groups represented by Formula (3), Z1 and Z2 may be the same or different from each other),
- where * is a bonding position of the substituent bonded to Ar2 or Ar3;
- R21 and R22 are independently a hydrogen atom or C1-4 alkyl;
- p is 0 or 1;
- q is an integer of 1 to 4;
- r is 0 or 1;
- p, q, and r satisfy 2≤p+q+r≤4;
- R21 may be the same or different and R22 may be the same or different when q is 2 or more;
- Ar21 is an (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 having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
- s is the number of R23s directly bonded to Ar21 and is an integer of 1 to 5;
- and R23s may be the same or different when s is 2 or more,
- where ** is a bonding position of the substituent bonded to Ar2 or Ar3;
- R31 and R32 are independently a hydrogen atom or C1-4 alkyl;
- t is an integer of 1 to 3;
- R31 may be the same or different and R32 may be the same or different when t is 2 or more;
- Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
- R33 is a fluorine atom, C1-4 alkyl having a fluorine atom as a substituent, or C1-3 alkoxy having a fluorine atom as a substituent;
- u is the number of R33s directly bonded to Ar31 and is an integer of 1 to 5;
- and R33s may be the same or different when u is 2 or more.
23 more elements
An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging unit, an exposure unit, a developing unit and a transfer unit, the electrophotographic photosensitive member comprising a support member bearing a photosensitive layer, said electrophotographic photosensitive member having a surface layer comprising a polymerization product of a hole transporting compound represented by Formula (1)
- where Ar1 is a substituted or unsubstituted aryl group;
- Ar2 and Ar3 are 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 selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, 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 Formula (2) or a monovalent group represented by Formula (3);
- Z2 is a hydrogen atom, a monovalent group represented by Formula (2), or a monovalent group represented by Formula (3);
- and when Z1 and Z2 are the monovalent groups represented by Formula (2)or when Z1 and Z2 are the monovalent groups represented by Formula (3), Z1 and Z2 may be the same or different from each other,
- where * is a bonding position of the substituent bonded to Ar2 or Ar3;
- R21 and R22 are independently a hydrogen atom or C1-4 alkyl;
- p is 0 or 1;
- q is an integer of 1 to 4;
- r is 0 or 1;
- p, q, and r satisfy 2≤p+q+r≤4;
- R21 may be the same or different and R22 may be the same or different when q is 2 or more;
- Ar21 is an (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 having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
- s is the number of R23s directly bonded to Ar21 and is an integer of 1 to 5;
- and R23s may be the same or different when s is 2 or more,
- where ** is a bonding position of the substituent bonded to Ar2 or Ar3;
- R31 and R32 are independently a hydrogen atom or C1-4 alkyl;
- t is an integer of 1 to 3;
- R31 may be the same or different and R32 may be the same or different when t is 2 or more;
- Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
- R33 is a fluorine atom, C1-4 alkyl having a fluorine atom as a substituent, or C1-3 alkoxy having a fluorine atom as a substituent;
- u is the number of R33s directly bonded to Ar31 and is an integer of 1 to 5;
- and R33s may be the same or different when u is 2 or more.
23 more elements
A process cartridge integrally supporting an electrophotographic photosensitive member and at least one of charging unit, a developing unit and a cleaning unit, and being attachable to and detachable from a main body of an electrophotographic apparatus, the electrophotographic photosensitive member comprising a support member bearing a photosensitive layer, said electrophotographic photosensitive member having a surface layer comprising a polymerization product of a hole transporting compound represented by Formula (1)
- where Ar1 is a substituted or unsubstituted aryl group;
- Ar2 and Ar3 are 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 selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, 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 Formula (2) or a monovalent group represented by Formula (3);
- Z2 is a hydrogen atom, a monovalent group represented by Formula (2), or a monovalent group represented by Formula (3);
- and when Z1 and Z2 are the monovalent groups represented by Formula (2)or when Z1 and Z2 are the monovalent groups represented by Formula (3), Z1 and Z2 may be the same or different from each other,
- where * is a bonding position of the substituent bonded to Ar2 or Ar3;
- R21 and R22 are independently a hydrogen atom or C1-4 alkyl;
- p is 0 or 1;
- q is an integer of 1 to 4;
- r is 0 or 1;
- p, q, and r satisfy 2≤p+q+r≤4;
- R21 may be the same or different and R22 may be the same or different when q is 2 or more;
- Ar21 is an (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 having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
- s is the number of R23s directly bonded to Ar21 and is an integer of 1 to 5;
- and R23s may be the same or different when s is 2 or more,
- where ** is a bonding position of the substituent bonded to Ar2 or Ar3;
- R31 and R32 are independently a hydrogen atom or C1-4 alkyl;
- t is an integer of 1 to 3;
- R31 may be the same or different and R32 may be the same or different when t is 2 or more;
- Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
- R33 is a fluorine atom, C1-4 alkyl having a fluorine atom as a substituent, or C1-3 alkoxy having a fluorine atom as a substituent;
- u is the number of R33s directly bonded to Ar31 and is an integer of 1 to 5;
- and R33s may be the same or different when u is 2 or more.
23 more elements
A manufacturing method of an electrophotographic photosensitive member having a support member bearing a photosensitive layer, said electrophotographic photosensitive member having a surface layer comprising a polymerization product of a hole transporting compound, the manufacturing method comprising the steps of:
- providing said support member bearing said photosensitive layer;
- forming thereon a coating film of a surface layer coating solution comprising a hole transporting compound represented by Formula (1);
- and
- forming said surface layer by polymerizing the hole transporting compound represented by Formula (1) in the coating film
- where Ar1 is a substituted or unsubstituted aryl group;
- Ar2 and Ar3 are 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 selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, 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 Formula (2) or a monovalent group represented by Formula (3);
- Z2 is a hydrogen atom, a monovalent group represented by Formula (2), or a monovalent group represented by Formula (3);
- and when Z1 and Z2 are the monovalent groups represented by Formula (2)or when Z1 and Z2 are the monovalent groups represented by Formula (3), Z1 and Z2 may be the same or different from each other,
- where * is a bonding position of the substituent bonded to Ar2 or Ar3;
- R21 and R22 are independently a hydrogen atom or C1-4 alkyl;
- p is 0 or 1;
- q is an integer of 1 to 4;
- r is 0 or 1;
- p, q, and r satisfy 2≤p+q+r≤4;
- R21 may be the same or different and R22 may be the same or different when q is 2 or more;
- Ar21 is an (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 having a fluorine atom as a substituent, or a methoxy group having a fluorine atom as a substituent;
- s is the number of R23s directly bonded to Ar21 and is an integer of 1 to 5;
- and R23s may be the same or different when s is 2 or more,
- where ** is a bonding position of the substituent bonded to Ar2 or Ar3;
- R31 R32 are independently a hydrogen atom or C1-4 alkyl;
- t is an integer of 1 to 3;
- R31 may be the same or different and R32 may be the same or different when t is 2 or more;
- Ar31 is a (u+1) valent group derived by removing (u+1) hydrogen atoms from substituted or unsubstituted arene;
- R33 is a fluorine atom, C1-4 alkyl having a fluorine atom as a substituent, or C1-3 alkoxy having a fluorine atom as a substituent;
- u is the number of R33s directly bonded to Ar31 and is an integer of 1 to 5;
- and R33s may be the same or different when u is 2 or more.
27 more elements
Dependencies are inferred from the claim text.