PHENOLIC COMPOUND, NOVEL RESOL RESIN, CURED PRODUCTS THEREOF, ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER CONTAINING THEM, AND PROCESS CARTRIDGE AND ELECTROPHOTOGRAPHIC APPARATUS WHICH HAVE THE ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER

• US 6,913,862 B2
• Filed: 12/18/2002
• Issued: 07/05/2005
• Est. Priority Date: 12/21/2001
• 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:
  US10/321,643
• Publication Number:
  US 20030175603A1
• Time in Patent Office: 930 Days
• Field of Search: 430/58.1, 430/58.7, 430/66, 399/262, 528/129
• US Class Current: 430/58.1
• CPC Class Codes: C08G 14/06 and monomers containing hydrogen attached to nitrogen
• CPC Class Codes: C08G 8/10 with phenol
• CPC Class Codes: C08G 8/12 with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
• CPC Class Codes: C08G 8/28 Chemically modified polycondensates
• CPC Class Codes: C08L 61/06 of aldehydes with phenols
• CPC Class Codes: C08L 61/14 Modified phenol-aldehyde condensates
• CPC Class Codes: G03G 5/06142 arylamine
• CPC Class Codes: G03G 5/061443 benzidine
• CPC Class Codes: G03G 5/06147 alkenylarylamine
• CPC Class Codes: G03G 5/0618 containing oxygen and nitrogen

Abstract

A phenolic compound having a plurality of substituted hydroxyphenyl groups and charge-transportable structure, the substituted hydroxyphenyl groups of which have a hydroxymethyl group; and a resol resin obtained by allowing a phenolic compound having hydroxyphenyl groups and charge-transportable structure, to react with formaldehyde in the presence of a basic catalyst, and having charge-transportable structure. Also disclosed are a cured product and an electrophotographic photosensitive member which make use of the above, 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 which contains a cured product of a phenolic compound;

said phenolic compound having a charge-transportable structure and

at least one substituted hydroxyphenyl group having a at least one hydroxymethyl group as a substituent.

2. The electrophotographic photosensitive member according to claim 1, wherein at least one of said at least one substituted hydroxyphenyl group is a substituted p-hydroxyphenyl group.

3. The electrophotographic photosensitive member according to claim 1, wherein at least one of said at least one hydroxymethyl group is linked at the position which is the o-position in respect to any of the hydroxyl groups of the at least one substituted hydroxyphenyl group having at least one hydroxymethyl group as a substituent.

4. The electrophotographic photosensitive member according to claim 1, wherein said charge-transportable structure is triarylamine structure.

5. The electrophotographic photosensitive member according to claim 1, wherein said phenolic compound has structure represented by any one of the following Formulas (1) to (5):

wherein R¹¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

R¹² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar¹¹ and Ar¹² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar¹³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group;

letter symbols m and n are each independently 0 or 1; and

X¹¹ to X¹⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X¹¹ to X¹⁴ is a hydroxymethyl group;

wherein R²¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar²¹ and Ar²² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R²¹;

a letter symbol p is 0 or 1; and

X²¹ and X²² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X²¹ and X²² is a hydroxymethyl group;

wherein R³¹ and R³² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar³¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R³¹ may combine to form a ring via R³¹;

the two benzene rings linked via R³² may combine to form a ring via R³²;

letter symbols q and r are each independently 0 or 1; and

X³¹ to X³⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X³¹ to X³⁴ is a hydroxymethyl group;

wherein R⁴¹ to R⁴³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁴¹ may combine to form a ring via R⁴¹;

the two benzene rings linked via R⁴² may combine to form a ring via R⁴²;

the two benzene rings linked via R⁴³ may combine to form a ring via R⁴³;

letter symbols s, t and u are each independently 0 or 1; and

X⁴¹ to X⁴⁶ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁴¹ to X⁴⁶ is a hydroxymethyl group; and

wherein R⁵² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z⁵¹ and Z⁵² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z⁵¹ and the benzene ring having Z⁵² may combine via Z⁵¹ or Z⁵² to form a ring;

a letter symbol v is 0 or 1;

a letter symbol w is an integer of 1 to 4; and

X⁵¹ and X⁵² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁵¹ and X⁵² is a hydroxymethyl group.

6. The electrophotographic photosensitive member according to claim 1, which has a protective layer on said photosensitive layer, and said surface layer of the electrophotographic photosensitive member is the protective layer.

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

said electrophotographic photosensitive member has a surface layer which contains a cured product of a resol resin obtained by allowing a phenolic compound, to react with formaldehyde in the presence of a basic catalyst;

said phenolic compound having a charge-transportable structure and at least one hydroxyphenyl group; and

said resol resin having charge-transportable structure.

8. The electrophotographic photosensitive member according to claim 7, wherein at least one of said at least one hydroxyphenyl group is a p-hydroxyphenyl group.

9. The electrophotographic photosensitive member according to claim 7, wherein said charge-transportable structure is triarylamine structure.

10. The electrophotographic photosensitive member according to claim 7, wherein said phenolic compound having at least one hydroxyphenyl group and charge-transportable structure has structure represented by any one of the following Formulas (6) to (10):

wherein R⁶¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched, R⁶² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar⁶¹ and Ar⁶² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar⁶³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group; and

letter symbols m′ and

n′

are each independently 0 or 1;

wherein R⁷¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁷¹ and Ar⁷² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R⁷¹; and

a letter symbol p′

is 0 or 1;

wherein R⁸¹ and R⁸² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁸¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R⁸¹ may combine to form a ring via R⁸¹;

the two benzene rings linked via R⁸² may combine to form a ring via R⁸²; and

letter symbols q′ and

r′

are each independently 0 or 1;

wherein R⁹¹ to R⁹³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁹¹ may combine to form a ring via R⁹¹;

the two benzene rings linked via R⁹² may combine to form a ring via R⁹²;

the two benzene rings linked via R⁹³ may combine to form a ring via R⁹³;

letter symbols s′

, t′ and

u′

are each independently 0 or 1; and

wherein R¹⁰² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z¹⁰¹ and Z¹⁰² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z¹⁰¹ and the benzene ring having Z¹⁰² may combine via Z¹⁰¹ or Z¹⁰² to form a ring;

a letter symbol v′

is 0 or 1; and

a letter symbol w′

is an integer of 1 to 4.

11. The electrophotographic photosensitive member according to claim 7, wherein said basic catalyst is an amine catalyst.

12. The electrophotographic photosensitive member according to claim 11, wherein said amine catalyst is a tertiary alkylamine.

13. The electrophotographic photosensitive member according to claim 7, wherein said basic catalyst is a catalyst containing an alkali metal or a catalyst containing an alkaline earth metal.

14. The electrophotographic photosensitive member according to claim 7, which has a protective layer on said photosensitive layer, and said surface layer of the electrophotographic photosensitive member is the protective layer.

15. A process cartridge comprising an electrophotographic photosensitive member and a 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, wherein;

said electrophotographic photosensitive member is an electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer;

said electrophotographic photosensitive member having a surface layer which contains a cured product of a phenolic compound;

said phenolic compound having a charge-transportable structure and at least one substituted hydroxyphenyl group having at least one hydroxymethyl group as a substituent.

16. The process cartridge according to claim 15 wherein at least one of said at least one substituted hydroxyphenyl group is a substituted p-hydroxyphenyl group.

17. The process cartridge according to claim 15 wherein at least one of said at least one hydroxymethyl group is linked at the position which is the o-position in respect to any of the hydroxyl groups of the at least one substituted hydroxyphenyl group having at least one hydroxymethyl group as a substituent.

18. The process cartridge according to claim 15 wherein said charge-transportable structure is triarylamine structure.

19. The process cartridge according to claim 15, wherein said phenolic compound has structure represented by any one of the following Formulas (1) to (5):

wherein R¹¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

R¹² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar¹¹ and Ar¹² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar¹³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group;

letter symbols m and n are each independently 0 or 1; and

X¹¹ to X¹⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X¹¹ to X¹⁴ is a hydroxymethyl group;

wherein R²¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar²¹ and Ar²² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R²¹;

a letter symbol p is 0 or 1; and

X²¹ and X²² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X²¹ and X²² is a hydroxymethyl group;

wherein R³¹ and R³² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar³¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R³¹ may combine to form a ring via R³¹;

the two benzene rings linked via R³² may combine to form a ring via R³²;

letter symbols q and r are each independently 0 or 1; and

X³¹ to X³⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X³¹ to X³⁴ is a hydroxymethyl group;

wherein R⁴¹ to R⁴³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁴¹ may combine to form a ring via R⁴¹;

the two benzene rings linked via R⁴² may combine to form a ring via R⁴²;

the two benzene rings linked via R⁴³ may combine to form a ring via R⁴³;

letter symbols s, t and u are each independently 0 or 1; and

X⁴¹ to X⁴⁶ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁴¹ to X⁴⁶ is a hydroxymethyl group; and

wherein R⁵² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z⁵¹ and Z⁵² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z⁵¹ and the benzene ring having Z⁵² may combine via Z⁵¹ or Z⁵² to form a ring;

a letter symbol v is 0 or 1;

a letter symbol w is an integer of 1 to 4; and

X⁵¹ and X⁵² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁵¹ and X⁵² is a hydroxymethyl group.

20. The process cartridge according to claim 15, wherein said surface layer of the electrophotographic photosensitive member is a protective layer.

21. 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, wherein;

said electrophotographic photosensitive member is an electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer;

said electrophotographic photosensitive member having a surface layer which contains a cured product of a resol resin obtained by allowing a phenolic compound having, to react with formaldehyde in the presence of a basic catalyst;

said phenolic compound having a charge-transportable structure and at least one hydroxyphenyl group; and

said resol resin having charge-transportable structure.

22. The process cartridge according to claim 21, wherein at least one of said at least one hydroxyphenyl group is a p-hydroxyphenyl group.

23. The process cartridge according to claim 21, wherein said charge-transportable structure is triarylamine structure.

24. The process cartridge according to claim 21, wherein said phenolic compound having at least one hydroxyphenyl group and charge-transportable structure has structure represented by any one of the following Formulas (6) to (10):

wherein R⁶¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched, R⁶² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar⁶¹ and Ar⁶² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar⁶³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group; and

letter symbols m′ and

n′

are each independently 0 or 1;

wherein R⁷¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁷¹ and Ar⁷² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R⁷¹; and

a letter symbol p′

is 0 or 1;

wherein R⁸¹ and R⁸² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁸¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R⁸¹ may combine to form a ring via R⁸¹;

the two benzene rings linked via R⁸² may combine to form a ring via R⁸²; and

letter symbols q′ and

r′

are each independently 0 or 1;

wherein R⁹¹ to R⁹³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁹¹ may combine to form a ring via R⁹²;

the two benzene rings linked via R⁹² may combine to form a ring via R⁹²;

the two benzene rings linked via R⁹³ may combine to form a ring via R⁹³;

letter symbols s′

, t′ and

u′

are each independently 0 or 1; and

wherein R¹⁰² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z¹⁰¹ and Z¹⁰² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z¹⁰¹ and the benzene ring having Z¹⁰² may combine via Z¹⁰¹ or Z¹⁰² to form a ring;

a letter symbol v′

is 0 or 1; and

a letter symbol w′

is an integer of 1 to 4.

25. The process cartridge according to claim 21, wherein said basic catalyst is an amine catalyst.

26. The process cartridge according to claim 25, wherein said amine catalyst is a tertiary alkylamine.

27. The process cartridge according to claim 21, wherein said basic catalyst is a catalyst containing an alkali metal or a catalyst containing an alkaline earth metal.

28. The process cartridge according to claim 21, wherein said electrophotographic photosensitive member has a protective layer on said photosensitive layer, and said surface layer of the electrophotographic photosensitive member is the protective layer.

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

said electrophotographic photosensitive member is an electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer;

said electrophotographic photosensitive member having a surface layer which contains a cured product of a phenolic compound;

said phenolic compound having a charge-transportable structure and at least one substituted hydroxyphenyl group having at least one hydroxymethyl group as a substituent.

30. The electrophotographic apparatus according to claim 29, wherein at least one of said at least one substituted hydroxyphenyl group is a substituted p-hydroxyphenyl group.

31. The electrophotographic apparatus according to claim 29, wherein at least one of said at least one hydroxymethyl group is linked at the position which is the o-position in respect to any of the hydroxyl groups of the at least one substituted hydroxyphenyl group having at least one hydroxymethyl group as a substituent.

32. The electrophotographic apparatus according to claim 29, wherein said charge-transportable structure is triarylamine structure.

33. The electrophotographic apparatus according to claim 29, wherein said phenolic compound has structure represented by any one of the following Formulas (1) to (5):

wherein R¹¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

R¹² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar¹¹ and Ar¹² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar¹³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group;

letter symbols m and n are each independently 0 or 1; and

X¹¹ to X¹⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X¹¹ to X¹⁴ is a hydroxymethyl group;

wherein R²¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar²¹ and Ar²² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R²¹;

a letter symbol p is 0 or 1; and

X²¹ and X²² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X²¹ and X²² is a hydroxymethyl group;

wherein R³¹ and R³² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar³¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R³¹ may combine to form a ring via R³¹;

the two benzene rings linked via R³² may combine to form a ring via R³²;

letter symbols q and r are each independently 0 or 1; and

X³¹ to X³⁴ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X³¹ to X³⁴ is a hydroxymethyl group;

wherein R⁴¹ to R⁴³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁴¹ may combine to form a ring via R⁴¹;

the two benzene rings linked via R⁴² may combine to form a ring via R⁴²;

the two benzene rings linked via R⁴³ may combine to form a ring via R⁴³;

letter symbols s, t and u are each independently 0 or 1; and

X⁴¹ to X⁴⁶ each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁴¹ to X⁴⁶ is a hydroxymethyl group; and

wherein R⁵² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z⁵¹ and Z⁵² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z⁵¹ and the benzene ring having Z⁵² may combine via Z⁵¹ or Z⁵² to form a ring;

a letter symbol v is 0 or 1;

a letter symbol w is an integer of 1 to 4; and

X⁵¹ and X⁵² each independently represent a hydrogen atom or a hydroxymethyl group, provided that at least one of X⁵¹ and X⁵² is a hydroxymethyl group.

34. The electrophotographic apparatus according to claim 29, wherein said electrophotographic photosensitive member has a protective layer on said photosensitive layer, and said surface layer of the electrophotographic photosensitive member is the protective layer.

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

said electrophotographic photosensitive member is an electrophotographic photosensitive member comprising a support and provided thereon a photosensitive layer;

said electrophotographic photosensitive member having a surface layer which contains a cured product of a resol resin obtained by allowing a phenolic compound, to react with formaldehyde in the presence of a basic catalyst;

said phenolic compound having a charge-transportable structure and at least one hydroxyphenyl group; and

said resol resin having charge-transportable structure.

36. The electrophotographic apparatus according to claim 35, wherein at least one of said at least one hydroxyphenyl group is a p-hydroxyphenyl group.

37. The electrophotographic apparatus according to claim 35, wherein said charge-transportable structure is triarylamine structure.

38. The electrophotographic apparatus according to claim 35, wherein said phenolic compound having at least one hydroxyphenyl group and charge-transportable structure has structure represented by any one of the following Formulas (6) to (10):

wherein R⁶¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched, R⁶² represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted phenyl group;

Ar⁶¹ and Ar⁶² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

Ar⁶³ represents a substituted or unsubstituted divalent aromatic hydrocarbon ring group or a substituted or unsubstituted divalent aromatic heterocyclic group; and

letter symbols m′ and

n′

are each independently 0 or 1;

wherein R⁷¹ represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁷¹ and Ar⁷² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings may combine to form a ring via R⁷¹; and

a letter symbol p′

is 0 or 1;

wherein R⁸¹ and Ar⁸² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Ar⁸¹ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the two benzene rings linked via R⁸¹ may combine to form a ring via R⁸¹;

the two benzene rings linked via R⁸² may combine to form a ring via R⁸²; and

letter symbols q′ and

r′

are each independently 0 or 1;

wherein R⁹¹ to R⁹³ each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

the two benzene rings linked via R⁹¹ may combine to form a ring via R⁹¹;

the two benzene rings linked via R⁹² may combine to form a ring via R⁹²;

the two benzene rings linked via R⁹³ may combine to form a ring via R⁹³;

letter symbols s′

, t′ and

u′

are each independently 0 or 1; and

wherein R¹⁰² represents a divalent hydrocarbon group having 1 to 8 carbon atoms and which may be branched;

Z¹⁰¹ and Z¹⁰² each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group or a substituted or unsubstituted monovalent aromatic heterocyclic group;

the benzene ring having Z¹⁰¹ and the benzene ring having Z¹⁰² may combine via Z¹⁰¹ or Z¹⁰² to form a ring;

a letter symbol v′

is 0 or 1; and

a letter symbol w′

is an integer of 1 to 4.

39. The electrophotographic apparatus according to claim 35, wherein said basic catalyst is an amine catalyst.

40. The electrophotographic apparatus according to claim 39, wherein said amine catalyst is a tertiary alkylamine.

41. The electrophotographic apparatus according to claim 35, wherein said basic catalyst is a catalyst containing an alkali metal or a catalyst containing an alkaline earth metal.

42. The electrophotographic apparatus according to claim 35, wherein said electrophotographic photosensitive member has a protective layer on said photosensitive layer, and said surface layer of the electrophotographic photosensitive member is the protective layer.