Electrophotographic photosensitive member, process for producing electrophotographic photosensitive member, and electrophotographic apparatus and process cartridge including electrophotographic photosensitive member
The present invention provides a satisfactory electrophotographic photosensitive member which satisfies wear resistance and electrical properties and further, with which image defects do not occur, a process for producing an electrophotographic photosensitive member, and an electrophotographic apparatus and a process cartridge each including the electrophotographic photosensitive member. The electrophotographic photosensitive member the surface layer of which contains a copolymer of a polymerizable functional group-containing charge transporting substance and a particular polymerizable compound.
1. An electrophotographic photosensitive member, comprising:
an electrically conductive support; and
a photosensitive layer on the support, wherein
a surface layer of the electrophotographic photosensitive member comprises a copolymer of a polymerizable functional group-containing charge transporting substance and a compound represented by formula (1):
where Ar is a substituted or unsubstituted aromatic hydrocarbon group and is an m-valent group obtained by eliminating m number of hydrogen atoms each bonded to a benzene ring of a compound represented by formula (2) other than from R 1 , R 2 and R 3 ;
Ln represents a divalent group represented by formula (3) or formula (4);
Fn represents a polymerizable functional group; and
m represents an integer of 1 to 4 and when m is equal to or larger than 2, m number of structures in parenthesis are the same or different:
where R 1 , R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted phenyl group; and
substituents on Ar, R 1 , R 2 and R 3 are each an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms:
where R 4 represents an alkylene group having 1 to 6 carbon atoms and p represents 0 or 1; and
R 5 represents an alkylene group having 1 to 6 carbon atoms and r represents an integer of 1 to 4.
2. The electrophotographic photosensitive member according to claim 1 , wherein the compound represented by the formula (1) is represented by formula (5):
where R 4 represents an alkylene group having 1 to 6 carbon atoms.
3. The electrophotographic photosensitive member according to claim 1 , wherein a number m of the polymerizable functional groups on Ar is 2 or 3.
4. The electrophotographic photosensitive member according to claim 1 , wherein Ar has a structure in which one polymerizable functional group on Ar is introduced to one benzene ring.
5. The electrophotographic photosensitive member according to claim 1 , wherein a ratio of a mass of the compound represented by formula (1) to a total mass of the polymerizable functional group-containing charge transporting substance and the compound represented by the formula (1) is 5 to 70% by mass.
6. The electrophotographic photosensitive member according to claim 1 , wherein the polymerizable functional group is a chain polymerizable functional group.
7. The electrophotographic photosensitive member according to claim 6 , wherein the chain polymerizable functional group is an acryloyloxy group or a methacryloyloxy group.
8. The electrophotographic photosensitive member according to claim 1 , wherein the compound represented by the formula (1) has a molecular weight of 400 to 700.
9. An electrophotographic photosensitive member, comprising:
an electrically conductive support; and
a photosensitive layer on the support, wherein
a surface layer of the electrophotographic photosensitive member comprises a copolymer of a polymerizable functional group-containing charge transporting substance and a compound represented by formula (1):
where Ar is a substituted or unsubstituted aromatic hydrocarbon group and is an m-valent group obtained by eliminating m number of hydrogen atoms each bonded to a benzene ring of a compound represented by structural formulae Ar-1 to Ar-6:
Ln represents a divalent group represented by formula (3) or formula (4);
Fn represents a polymerizable functional group; and
m represents an integer of 1 to 4 and when m is equal to or larger than 2, m number of structures in parenthesis are the same or different:
the benzene rings of formulae Ar-1 to Ar-6 are each independently optionally substituted with R 1 , where R 1 independently represents a hydrogen atom or a substituted or unsubstituted phenyl group; and
substituents on Ar and R 1 are independently each an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms:
where R 4 represents an alkylene group having 1 to 6 carbon atoms and p represents 0 or 1; and
R 5 represents an alkylene group having 1 to 6 carbon atoms and r represents an integer of 1 to 4.
10. The electrophotographic photosensitive member according to claim 9 , wherein the compound represented by the formula (1) has a molecular weight of 400 to 700.
11. The electrophotographic photosensitive member according to claim 9 , wherein the compound represented by the formula (1) is represented by formula (5):
where R 4 represents an alkylene group having 1 to 6 carbon atoms.
12. The electrophotographic photosensitive member according to claim 9 , wherein a number m of the polymerizable functional groups on Ar is 2 or 3.
13. The electrophotographic photosensitive member according to claim 9 , wherein Ar has a structure in which one polymerizable functional group on Ar is introduced to one benzene ring.
14. The electrophotographic photosensitive member according to claim 9 , wherein a ratio of a mass of the compound represented by formula (1) to a total mass of the polymerizable functional group-containing charge transporting substance and the compound represented by the formula (1) is 5 to 70% by mass.
15. The electrophotographic photosensitive member according to claim 9 , wherein the polymerizable functional group is a chain polymerizable functional group.
16. The electrophotographic photosensitive member according to claim 15 , wherein the chain polymerizable functional group is an acryloyloxy group or a methacryloyloxy group.
17. A process cartridge integrally supporting: an electrophotographic photosensitive member comprising an electrically conductive support and a photosensitive layer on the support; and at least one unit selected from the group consisting of a charging unit, a developing unit and a cleaning unit, the process cartridge detachably attachable to an electrophotographic apparatus main body, wherein
a surface layer of the electrophotographic photosensitive member comprises a copolymer of a polymerizable functional group-containing charge transporting substance and a compound represented by formula (1):
where Ar is a substituted or unsubstituted aromatic hydrocarbon group and is an m-valent group obtained by eliminating m number of hydrogen atoms each bonded to a benzene ring of a compound represented by formula (2) other than from R 1 , R 2 and R 3 ;
Ln represents a divalent group represented by formula (3) or formula (4);
Fn represents a polymerizable functional group; and
m represents an integer of 1 to 4 and when m is equal to or larger than 2, m number of structures in parenthesis are the same or different:
where R 1 , R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted phenyl group; and
substituents on Ar, R 1 , R 2 and R 3 are each an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms:
where R 4 represents an alkylene group having 1 to 6 carbon atoms and p represents 0 or 1; and
R 5 represents an alkylene group having 1 to 6 carbon atoms and r represents an integer of 1 to 4.
18. An electrophotographic apparatus, comprising:
an electrophotographic photosensitive member comprising an electrically conductive support and a photosensitive layer on the support;
a charging unit;
an exposing unit;
a developing unit; and
a transfer unit, wherein
a surface layer of the electrophotographic photosensitive member comprises a copolymer of a polymerizable functional group-containing charge transporting substance and a compound represented by formula (1):
where Ar is a substituted or unsubstituted aromatic hydrocarbon group and is an m-valent group obtained by eliminating m number of hydrogen atoms each bonded to a benzene ring of a compound represented by formula (2) other than from R 1 , R 2 and R 3 ;
Ln represents a divalent group represented by formula (3) or formula (4);
Fn represents a polymerizable functional group; and
m represents an integer of 1 to 4 and when m is equal to or larger than 2, m number of structures in parenthesis are the same or different:
where R 1 , R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted phenyl group; and
substituents on Ar, R 1 , R 2 and R 3 are each an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms:
where R 4 represents an alkylene group having 1 to 6 carbon atoms and p represents 0 or 1; and
R 5 represents an alkylene group having 1 to 6 carbon atoms and r represents an integer of 1 to 4.
19. A process for producing an electrophotographic photosensitive member comprising: an electrically conductive support; and a photosensitive layer on the support, the process comprising polymerizing a coating film of a coating liquid prepared by mixing a polymerizable functional group-containing charge transporting substance and a compound represented by formula (1), thereby forming a surface layer of the electrophotographic photosensitive member:
where Ar is a substituted or unsubstituted aromatic hydrocarbon group and is an m-valent group obtained by eliminating m number of hydrogen atoms each bonded to a benzene ring of a structure represented by formula (2) other than from R 1 , R 2 and R 3 ;
Ln represents a divalent group represented by formula (3) or formula (4);
Fn represents a polymerizable functional group; and
m represents an integer of 1 to 4 and when m is equal to or larger than 2, m number of structures in parenthesis are the same or different:
where R 1 , R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted phenyl group; and
substituents on Ar, R 1 , R 2 and R 3 are each an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms:
where R 4 represents an alkylene group having 1 to 6 carbon atoms and p represents 0 or 1; and
R 5 represents an alkylene group having 1 to 6 carbon atoms and r represents an integer of 1 to 4.