Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

Patent metadata

Field	Value
Publication number	US-9594318-B2
Application number	US-201514832421-A
Country	US
Kind code	B2
Filing date	Aug 21, 2015
Priority date	Sep 4, 2014
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

Provided is an electrophotographic photosensitive member, including: a support; and a photosensitive layer formed on the support, in which a surface layer of the electrophotographic photosensitive member contains a polymerized product of a compound represented by the following structural formula (1).

First claim

What is claimed is:

1. An electrophotographic photosensitive member, comprising:
a support; and
a photosensitive layer formed on the support,
wherein a surface layer of the electrophotographic photosensitive member contains a polymerized product of a hole transportable compound represented by the following structural formula (1):

in the structural formula (1):
Ar represents a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group, and a substituent of the condensed polycyclic aromatic hydrocarbon group is a group selected from the group consisting of an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, and a halogen-substituted alkyl group;
Ph represents a substituted or unsubstituted group obtained by removing q+1 hydrogen atoms from benzene, and a substituent of the group obtained by removing q+1 hydrogen atoms from benzene is a group selected from the group consisting of an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, and a halogen-substituted alkyl group;
Ar and Ph are bonded to each other through an aromatic ring in Ar and Ph;
R represents a linear or branched alkylene group having 1 to 12 carbon atoms;
Fn represents a reactive functional group said reactive functional group being an acryloyloxy group or a methacryloyloxy group;
m and n each independently represent 0 or 1;
p represents an integer of 0 or more and 4 or less, and when p represents 2 or more, structures in p sets of parentheses may be identical to or different from each other, provided that when p represents 2 or more, a case where oxygen atoms (O) are continuous is excluded;
q represents an integer of 0 or more and 3 or less, and when q represents 2 or more, structures in q sets of parentheses may be identical to or different from each other;
r represents an integer of 1 or more and 6 or less, and when r represents 2 or more, structures in r sets of parentheses may be identical to or different from each other;
the structural formula (1) has at least one Fn;
a structure except Fn in the structural formula (1) has a conjugated structure containing 20 or more sp2 carbon atoms; and
the 20 or more sp2 carbon atoms in the conjugated structure are continuously bonded to each other.

2. An electrophotographic photosensitive member according to claim 1 , wherein a structure except Fn in the structural formula (1) has a conjugated structure containing 24 or more sp2 carbon atoms.

3. An electrophotographic photosensitive member according to claim 1 , wherein the condensed polycyclic aromatic hydrocarbon group is a group obtained by removing r hydrogen atoms from one of fluorene, anthracene, phenanthrene, fluoranthene, and pyrene.

4. An electrophotographic photosensitive member according to claim 1 , wherein the surface layer has an ionization potential of 5.5 eV or more and 6.4 eV or less.

5. An electrophotographic photosensitive member according to claim 4 , wherein the surface layer has an ionization potential of 5.8 eV or more and 6.2 eV or less.

6. An electrophotographic photosensitive member according to claim 1 , wherein:
the electrophotographic photosensitive member comprises a first hole transporting layer and a second hole transporting layer;
the second hole transporting layer is the surface layer; and
the first hole transporting layer has an ionization potential of 5.0 eV or more and 6.0 eV or less.

7. An electrophotographic photosensitive member according to claim 6 , wherein the first hole transporting layer has an ionization potential of 5.2 eV or more and 5.8 eV or less.

8. An electrophotographic photosensitive member according to claim 1 , wherein the compound represented by the structural formula (1) has a molecular weight of 300 or more and 1,000 or less.

9. A process cartridge, comprising:
a electrophotographic photosensitive member; and
at least one unit selected from the group consisting of a charging unit, a developing unit, a transferring unit, and a cleaning unit,
the electrophotographic photosensitive member and the at least one unit being integrally supported,
wherein the process cartridge is detachably mountable to a main body of an electrophotographic apparatus,
the electrophotographic photosensitive member comprising:
a support; and
a photosensitive layer formed on the support, wherein
a surface layer of the electrophotographic photosensitive member contains a polymerized product of a hole transportable compound represented by the following structural formula (1):

in the structural formula (1):
Ar represents a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group, and a substituent of the condensed polycyclic aromatic hydrocarbon group is a group selected from the group consisting of an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, and a halogen-substituted alkyl group;
Ph represents a substituted or unsubstituted group obtained by removing q+1 hydrogen atoms from benzene, and a substituent of the group obtained by removing q+1 hydrogen atoms from benzene is a group selected from the group consisting of an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, and a halogen-substituted alkyl group;
Ar and Ph are bonded to each other through an aromatic ring in Ar and Ph;
R represents a linear or branched alkylene group having 1 to 12 carbon atoms;
Fn represents a reactive functional group, said reactive functional group being an acryloyloxy group or a methacryloyloxy group;
m and n each independently represent 0 or 1;
p represents an integer of 0 or more and 4 or less, and when p represents 2 or more, structures in p sets of parentheses may be identical to or different from each other, provided that when p represents 2 or more, a case where oxygen atoms (O) are continuous is excluded;
q represents an integer of 0 or more and 3 or less, and when q represents 2 or more, structures in q sets of parentheses may be identical to or different from each other;
r represents an integer of 1 or more and 6 or less, and when r represents 2 or more, structures in r sets of parentheses may be identical to or different from each other;
the structural formula (1) has at least one Fn;
a structure except Fn in the structural formula (1) has a conjugated structure containing 20 or more sp2 carbon atoms; and
the 20 or more sp2 carbon atoms in the conjugated structure are continuously bonded to each other.

10. An electrophotographic apparatus, comprising:
a electrophotographic photosensitive member;
a charging unit;
an exposing unit;
a developing unit; and
a transferring unit,
the electrophotographic photosensitive member comprising:
a support; and
a photosensitive layer formed on the support, wherein
a surface layer of the electrophotographic photosensitive member contains a polymerized product of a hole transportable compound represented by the following structural formula (1):

in the structural formula (1):
Ar represents a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group, and a substituent of the condensed polycyclic aromatic hydrocarbon group is a group selected from the group consisting of an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, and a halogen-substituted alkyl group;
Ph represents a substituted or unsubstituted group obtained by removing q+1 hydrogen atoms from benzene, and a substituent of the

Assignees

• Canon Kk

Inventors

• Nakata Koichi
• Takagi Shinji
• Nonaka Masaki
• Tokimitsu Ryoichi
• Mori Haruki

Classifications

• G03G5/14786 Primary

  Macromolecular compounds characterised by specific side-chain substituents or end groups · CPC title

• G03G5/047

  characterised by the charge-generation layers or charge transport layers {(G03G5/0433 and G03G5/0436 take precedence)} · CPC title