Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus

• US 7,022,446 B2
• Filed: 07/11/2003
• Issued: 04/04/2006
• Est. Priority Date: 07/15/2002
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Yoshimura, Kimihiro, Tanaka, Daisuke, Ikezue, Tatsuya, Morikawa, Yosuke, Nakata, Kouichi
• Primary Examiner(s): Goodrow, John L
• Application Number:
  US10/616,944
• Publication Number:
  US 20040023139A1
• Time in Patent Office: 998 Days
• Field of Search: 430/59.6, 430/96, 430/66
• US Class Current: 430/59.6
• CPC Class Codes: G03G 5/0564 Polycarbonates
• CPC Class Codes: G03G 5/0567 Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
• CPC Class Codes: G03G 5/0575 Other polycondensates comprising nitrogen atoms with or without oxygen atoms in the main chain
• CPC Class Codes: G03G 5/0592 Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
• CPC Class Codes: G03G 5/14747 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03G 5/14791 Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity

Abstract

An electrophotographic photosensitive member having a surface layer containing at least one of a charge-transporting material and conductive particles and a polymer obtained by polymerizing at least one selected from the group consisting of a polyhydroxymethylbisphenol monomer having a specific structure, a polyhydroxymethylbisphenol oligomer having a specific structure, a polyhydroxymethyltrisphenol monomer having a specific structure and a polyhydroxymethyltrisphenol oligomer having a specific structure; and a process cartridge and an electrophotographic apparatus which have the electrophotographic photosensitive member.

Claims

1. An electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.

2. An electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing a polyhydroxymethylbisphenol monomer having a structure represented by the following Formula (1);

 

wherein X¹¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R¹¹ to R¹⁴ each independently represent a hydroxymethyl group, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms other than the hydroxymethyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms, provided that at least two of the R¹¹ to R¹⁴ are each a hydroxymethyl group.

3. The electrophotographic photosensitive member according to claim 2, wherein the X¹¹ in Formula (1) is a divalent group having 3 or more carbon atoms.

4. The electrophotographic photosensitive member according to claim 3, wherein the X¹¹ in Formula (1) is a divalent group having 5 or more carbon atoms and having a cyclic structure.

5. The electrophotographic photosensitive member according to claim 2, wherein the X¹¹ in Formula (1) is a divalent group having a benzene ring.

6. The electrophotographic photosensitive member according to claim 2, wherein the X¹¹ in Formula (1) is an ether group, a thioether group or a di(trifluoromethyl)methylene group.

7. An electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing a polyhydroxymethylbisphenol oligomer having a structure in which a bisphenol monomer having a structure represented by the following Formula (2) has been condensed through a methylene group;

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.

8. The electrophotographic photosensitive member according to claim 7, wherein the X²¹ in Formula (2) is a divalent group having 3 or more carbon atoms.

9. The electrophotographic photosensitive member according to claim 8, wherein the X²¹ in Formula (2) is a divalent group having 5 or more carbon atoms and having a cyclic structure.

10. The electrophotographic photosensitive member according to claim 7, wherein the X²¹ in Formula (2) is a divalent group having a benzene ring.

11. The electrophotographic photosensitive member according to claim 7, wherein the X²¹ in Formula (2) is an ether group, a thioether group or a di(trifluoromethyl) methylene group.

12. A process cartridge comprising an electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means, a transfer means and a cleaning means which are integrally supported, and being detachably mountable to the main body of an electrophotographic apparatus;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing

(i) a polyhydroxymethylbisphenol monomer having a structure represented by the following Formula (1);

 

wherein X¹¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R¹¹ to R¹⁴ each independently represent a hydroxymethyl group, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms other than the hydroxymethyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms, provided that at least two of the R¹¹ to R¹⁴ are each a hydroxymethyl group or (ii) a polyhydroxymethylbisphenol oligomer having a structure in which a bisphenol monomer having a structure represented by the following Formula (2) has been condensed through a methylene group;

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.

13. An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging means, an exposure means, a developing means and a transfer means;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing

(i) a polyhydroxymethylbisphenol monomer having a structure represented by the following Formula (1);

 

wherein X¹¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R¹¹ to R¹⁴ each independently represent a hydroxymethyl group, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms other than the hydroxymethyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms, provided that at least two of the R¹¹ to R¹⁴ are each a hydroxymethyl group or

(ii) a polyhydroxymethylbisphenol oligomer having a structure in which a bisphenol monomer having a structure represented by the following Formula (2) has been condensed through a methylene group;

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.

14. A process cartridge comprising an electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means, a transfer means and a cleaning means which are integrally supported, and being detachably mountable to the main body of an electrophotographic apparatus;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing a polyhydroxymethylbisphenol monomer having a structure represented by the following Formula (1);

 

wherein X¹¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided hat a case in which both the R⁰¹ and R⁰² are substituted or, unsubstituted phenyl groups is excluded; and

R¹¹ to R¹⁴ each independently represent a hydroxymethyl group, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms other than the hydroxymethyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms, provided that at least two of the R¹¹ to R¹⁴ are each a hydroxymethyl group.

15. An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging means, an exposure means, a developing means and a transfer means;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing a polyhydroxymethylbisphenol monomer having a structure represented by the following Formula (1);

 

wherein X¹¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R¹¹ to R¹⁴ each independently represent a hydroxymethyl group, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms other than the hydroxymethyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms, provided that at least two of the R¹¹ to R¹⁴ are each a hydroxymethyl group.

16. A process cartridge comprising an electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means, a transfer means and a cleaning means which are integrally supported, and being detachably mountable to the main body of an electrophotographic apparatus;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing polyhydroxymethylbisphenol oligomer having a structure in which a bisphenol monomer having a structure represented by the following Formula (2) has been condensed through a methylene group;

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.

17. An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging means, an exposure means, a developing means and a transfer means;

the electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer, wherein;

said electrophotographic photosensitive member has a surface layer containing;

at least one of a charge-transporting material and conductive particles; and

a polymer obtained by polymerizing a polyhydroxymethylbisphenol oligomer having a structure in which a bisphenol monomer having a structure represented by the following Formula (2) has been condensed through a methylene group;

 

wherein X²¹ represents a single bond, a carbonyl group, an ether group, a thioether group or a —

CR⁰¹R⁰²-group, where R⁰¹ and R⁰² each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group, or represent a substituted or unsubstituted cycloalkylidene group having 3 to 6 carbon atoms which is formed by combination of R⁰¹ with R⁰², provided that a case in which both the R⁰¹ and R⁰² are substituted or unsubstituted phenyl groups is excluded; and

R²¹ to R²⁴ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted alkoxyl group having 1 to 4 carbon atoms.