Electrophotographic photosensitive member, method for producing the same, process cartridge and electrophotographic apparatus

Patent metadata

Field	Value
Publication number	US-10042272-B2
Application number	US-201715483252-A
Country	US
Kind code	B2
Filing date	Apr 10, 2017
Priority date	Apr 14, 2016
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

To provide an electrophotographic photosensitive member being excellent in abrasion resistance and having good electrical characteristics. The surface layer of the electrophotographic photosensitive member contains a copolymerized product of a hole transporting compound having a specified structure and a compound having a specified structure.

First claim

What is claimed is:

1. An electrophotographic photosensitive member comprising:
a support; and
a photosensitive layer on the support, wherein
a surface layer of the electrophotographic photosensitive member comprises a copolymerized product of a hole transporting compound having an acryloyloxy group or a methacryloyloxy group and having a triphenylamine backbone, and a compound represented by formula (1) or formula (2):

where m 1 represents 2 and X 1 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 2 to 18 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 12 carbon atoms, and an arene having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 12 carbon atoms, provided that the number of carbon atoms in X 1 is 2 to 18; and

where m 2 represents 1, m 3 represents 1, and Y 1 represents an oxygen atom or a sulfur atom,
X 2 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and an arene having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and
X 3 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms, unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and an arene having 6 to 12 carbon atoms, unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms,
provided that the total number of carbon atoms in X 2 and X 3 is 2 to 16.

2. The electrophotographic photosensitive member according to claim 1 , wherein X 1 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 2 to 18 carbon atoms, and a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 12 carbon atoms,
X 2 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, and a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and
X 3 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, and a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms.

3. The electrophotographic photosensitive member according to claim 1 , wherein X 1 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 2 to 18 carbon atoms,
X 2 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 1 to 15 carbon atoms, and
X 3 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 1 to 15 carbon atoms.

4. The electrophotographic photosensitive member according to claim 1 , wherein X 1 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 2 6 carbon atoms,
X 2 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 1 to 3 carbon atoms, and
X 3 represents a 2-valent group obtained by removing 2 hydrogen atoms from a linear or branched alkane having 1 3 carbon atoms,
provided that the total number of carbon atoms in X 2 and X 3 is 2 to 4.

5. The electrophotographic photosensitive member according to claim 1 , wherein the hole transporting compound having a triphenylamine backbone is a compound represented by formula (3):
(P 1 a Z  (3)

where P 1 represents a group represented by formula (4) or formula (5); “a” represents an integer of 2 to 4, and P 1 s may be the same or different; Z represents a hole transporting group, and a hydrogenated product in which a binding moiety of Z and P 1 is replaced with a hydrogen atom is a compound represented by formula (6) or formula (7):

where R 4 , R 5 and R 6 represent a phenyl group which may have an alkyl group having 1 to 6 carbon atoms as a substituent; and R 4 , R 5 and R 6 may be each the same or different; and

where R 7 , R 8 , R 9 and R 10 represent a phenyl group which may have an alkyl group having 1 to 6 carbon atoms as a substituent; and R 7 , R 8 , R 9 and R 10 may be each the same or different.

6. The electrophotographic photosensitive member according to claim 1 , wherein 0.05≤Mb/(Ma+Mb)≤0.50 when content mass of the hole transporting compound contained in the surface layer is designated as Ma and content mass of the compound represented by formula (1) or formula (2) contained in the surface layer is designated as Mb.

7. A method for producing an electrophotographic photosensitive member comprising a support and a surface layer on the support, the method comprising:
preparing a coating liquid for a surface layer, the coating liquid comprising a hole transporting compound having an acryloyloxy group or a methacryloyloxy group and having a triphenylamine backbone, and a compound represented by formula (1) or formula (2), and
forming a coating film of the coating liquid for a surface layer, and curing the coating film to thereby form a surface layer:

where m 1 represents 2 and X 1 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 2 to 18 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 12 carbon atoms, and an arene having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 12 carbon atoms, provided that the number of carbon atoms in X 1 is 2 to 18; and

where m 2 represents 1, m 3 represents 1, and Y 1 represents an oxygen atom or a sulfur atom,
X 2 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and an arene having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and
X 3 represents a 2-valent group obtained by removing 2 hydrogen atoms from any of a linear or branched alkane having 1 to 15 carbon atoms, a cyclic or polycyclic alkane having 6 to 12 carbon atoms unsubstituted or having a linear or branched alkyl group having 1 to 9 carbon atoms, and an arene having 6 to 12 carbon atoms unsubstituted or having a linear or branched al

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G5/14717

  obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• G03G5/14795

  Macromolecular compounds characterised by their physical properties · CPC title

• G03G5/142

  Inert intermediate layers · CPC title

• G03G5/071 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds (G03G5/078 takes precedence) · CPC title

• G03G5/047

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