Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

• US 20030232263A1
• Filed: 04/25/2003
• Published: 12/18/2003
• Est. Priority Date: 04/26/2002
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Ishiduka, Yuka, Ogaki, Harunobu, Yoshida, Akira, Takaya, Itaru, Tanaka, Takakazu
• Granted Patent: US 6,991,881 B2
• Time in Patent Office: Days
• US Class Current: 430/58.7
• CPC Class Codes: C08J 2479/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: G03G 5/075 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds G03G5/078 takes precedence
• CPC Class Codes: G03G 5/0763 comprising arylamine moiety
• CPC Class Codes: G03G 5/0764 triarylamine

Abstract

The present invention relates to an electrophotographic photosensitive member having a support and provided thereon a photosensitive layer. The photosensitive layer contains a high-molecular weight charge-transporting material having a specific repeating structural unit. The high-molecular weight charge-transporting material has a weight-average molecular weight Mw of 1,500 or more and an energy level of highest occupied molecular orbital, E_HOMO, of from −8.3 eV or more to −8.0 eV or less as found by semiempirical molecular-orbital calculation. The present invention also relates to a process cartridge and an electrophotographic apparatus which have such an electrophotographic photosensitive member.

Claims

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

said photosensitive layer contains a high-molecular weight charge-transporting material having a repeating structural unit represented by the following formula (1); and

the high-molecular weight charge-transporting material has;

a weight-average molecular weight Mw of 1,500 or more; and

an energy level of highest occupied molecular orbital, E_HOMO, of from −

8.3 eV or more to −

8.0 eV or less as found by semiempirical molecular-orbital calculation;

 

wherein Ar¹¹ represents a substituted or unsubstituted monovalent aromatic ring group or a substituted or unsubstituted monovalent heterocyclic ring group; and

Ar¹² represents a divalent group having a structure selected from the group consisting of structures represented by the following formulas (2), (2)′ and

(2)″

;

 

wherein;

in the formula (2), Ar²¹ and Ar²² each independently represent a substituted or unsubstituted trivalent aromatic ring group or a substituted or unsubstituted trivalent heterocyclic ring group;

A²¹ and A²² each independently represent a single bond, or a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c represents 0 or 1 and, when c is 0, it represents that Ar²¹ and Ar²² stand combined directly;

in the formula (2)′

, Ar^21′

and Ar^22′

each independently represent a substituted or unsubstituted divalent aromatic ring group or a substituted or unsubstituted divalent heterocyclic ring group;

A^21′

represents a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c′

represents 0 or 1 and, when c′

is 0, it represents that Ar^21′

and Ar^22′

stand combined directly; and

in the formula (2)″

, Ar^21″

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

letter symbol c″

represents an integer of 1 or more, provided that, when c″

is two or more, the two or more Ar^21″

'"'"'s may be the same or different.

2. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has an electron-attracting group.

3. The electrophotographic photosensitive member according to claim 2, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (11):

4. The electrophotographic photosensitive member according to claim 3, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (12):

5. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (21):

6. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (22):

7. The electrophotographic photosensitive member according to claim 5, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (23):

8. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (31):

9. The electrophotographic photosensitive member according to claim 8, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (32):

10. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (41):

11. The electrophotographic photosensitive member according to claim 10, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (42):

12. The electrophotographic photosensitive member according to claim 1, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (51):

13. The electrophotographic photosensitive member according to claim 12, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (52):

14. The electrophotographic photosensitive member according to claim 12, wherein said high-molecular weight charge-transporting material has a repeating structural unit represented by the following formula (53):

15. The electrophotographic photosensitive member according to claim 1, wherein said photosensitive layer is a surface layer of the electrophotographic photosensitive member.

16. The electrophotographic photosensitive member according to claim 15, wherein said photosensitive layer contains a polycarbonate.

17. The electrophotographic photosensitive member according to claim 15, wherein said photosensitive layer contains a polyarylate.

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

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

said photosensitive layer contains a high-molecular weight charge-transporting material having a repeating structural unit represented by the following formula (1); and

the high-molecular weight charge-transporting material has;

a weight-average molecular weight Mw of 1,500 or more; and

an energy level of highest occupied molecular orbital, E_HOMO, of from −

8.3 eV or more to −

8.0 eV or less as found by semiempirical molecular-orbital calculation;

 

wherein Ar¹¹ represents a substituted or unsubstituted monovalent aromatic ring group or a substituted or unsubstituted monovalent heterocyclic ring group; and

Ar¹² represents a divalent group having a structure selected from the group consisting of structures represented by the following formulas (2), (2)′ and

(2)″

;

 

wherein;

in the formula (2), Ar²¹ and Ar²² each independently represent a substituted or unsubstituted trivalent aromatic ring group or a substituted or unsubstituted trivalent heterocyclic ring group;

A²¹ and A²² each independently represent a single bond, or a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c represents 0 or 1 and, when c is 0, it represents that Ar²¹ and Ar²² stand combined directly;

in the formula (2)′

, Ar^21′

and Ar^22′

each independently represent a substituted or unsubstituted divalent aromatic ring group or a substituted or unsubstituted divalent heterocyclic ring group;

A^21′

represents a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c′

represents 0 or 1 and, when c′

is 0, it represents that Ar^21′

and Ar^22′

stand combined directly; and

in the formula (2)″

, Ar^21″

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

letter symbol c″

represents an integer of 1 or more, provided that, when c″

is two or more, the two or more Ar^21″

'"'"'s may be the same or different.

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

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

said photosensitive layer contains a high-molecular weight charge-transporting material having a repeating structural unit represented by the following formula (1); and

the high-molecular weight charge-transporting material has;

a weight-average molecular weight Mw of 1,500 or more; and

an energy level of highest occupied molecular orbital, E_HOMO, of from −

8.3 eV or more to −

8.0 eV or less as found by semiempirical molecular-orbital calculation;

 

wherein Ar¹¹ represents a substituted or unsubstituted monovalent aromatic ring group or a substituted or unsubstituted monovalent heterocyclic ring group; and

Ar¹² represents a divalent group having a structure selected from the group consisting of structures represented by the following formulas (2), (2)′ and

(2)″

;

 

wherein;

in the formula (2), Ar²¹ and Ar²² each independently represent a substituted or unsubstituted trivalent aromatic ring group or a substituted or unsubstituted trivalent heterocyclic ring group;

A²¹ and A²² each independently represent a single bond, or a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c represents 0 or 1 and, when c is 0, it represents that Ar²¹ and Ar²² stand combined directly;

in the formula (2)′

, Ar^21′

and Ar^22′

each independently represent a substituted or unsubstituted divalent aromatic ring group or a substituted or unsubstituted divalent heterocyclic ring group;

A^21′

represents a Group 14 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group or an electron-attracting group, or a Group 15 element having a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an electron-attracting group, or a Group 16 element; and

letter symbol c′

represents 0 or 1 and, when c′

is 0, it represents that Ar<sup>21′ and

Ar22′</sup>

stand combined directly; and

in the formula (2)″

, Ar^21″

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

letter symbol c″

represents an integer of 1 or more, provided that, when c″

is two or more, the two or more Ar^21″

'"'"'s may be the same or different.