Electrophotographic photosensitive member, and electrophotographic apparatus and process cartridge which make use of the same

• US 20050181292A1
• Filed: 11/05/2004
• Published: 08/18/2005
• Est. Priority Date: 11/26/2003
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Tanaka, Masato, Fujii, Atsushi
• Granted Patent: US 7,276,318 B2
• Time in Patent Office: Days
• US Class Current: 430/72
• CPC Class Codes: G03G 5/0679 Disazo dyes
• CPC Class Codes: G03G 5/0681 containing hetero rings in the part of the molecule between the azo-groups
• CPC Class Codes: G03G 5/0683 containing polymethine or anthraquinone groups

Abstract

This invention relates to an electrophotographic photosensitive member having a support and a photosensitive layer.
In the electrophotographic photosensitive member having a support and a photosensitive layer, which electrophotographic photosensitive member makes use of, as writing light, a semiconductor laser light ray having a wavelength of from 380 to 500 nm, the photosensitive layer contains a bisazo pigment represented by the following Formula (1):
wherein A₁, A₂ and A₃ may be the same or different, and each independently represent a saturated or unsaturated aliphatic hydrocarbon group which may have a substituent, an aromatic hydrocarbon ring group which may have a substituent, a heterocyclic ring group which may have a substituent, or a carbonyl group; R₁ and R₂ may be the same or different, and each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a halogen atom; R₃, R₄, R₅ and R₆ may be the same or different, and each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a heterocyclic ring group which may have a substituent, or an aralkyl group which may have a substituent, provided that R₃ and R₄, and R₅ and R₆, may each form a cyclic amino group via the nitrogen atom in the formula; Z₁ and Z₂ each independently represent an oxygen atom or a sulfur atom; m₁ and m₂ each represent an integer of 0 to 4; and n₁, n₂ and n₃ each independently represent 0 or 1.

Claims

1. An electrophotographic photosensitive member comprising a support and a photosensitive layer, and making use of, as writing light, a semiconductor laser light having a wavelength of from 380 to 500 nm, wherein

said photosensitive layer comprises a bisazo pigment represented by the following Formula (1):

wherein A₁, A₂ and A₃ each independently represent a saturated or unsaturated aliphatic hydrocarbon group which may have a substituent, an aromatic hydrocarbon ring group which may have a substituent, a heterocyclic ring group which may have a substituent, or a carbonyl group;

R₁ and R₂ each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a halogen atom;

R₃, R₄, R₅ and R₆ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a heterocyclic ring group which may have a substituent, or an aralkyl group which may have a substituent, provided that R₃ and R₄, and R₅ and R₆, may each form a cyclic amino group via the nitrogen atom in the formula;

Z₁ and Z₂ each independently represent an oxygen atom or a sulfur atom;

m₁ and m₂ each represent an integer of 0 to 4; and

n₁, n₂ and n₃ each independently represent 0 or 1.

2. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), R₃ and R₅ are each a hydrogen atom and Z₁ and Z₂ are each an oxygen atom.

3. The electrophotographic photosensitive member according to claim 2, wherein, in said Formula (1), R₄ and R₆ are each independently an aryl group which may have a substituent.

4. The electrophotographic photosensitive member according to claim 3, wherein, in said Formula (1), R₄ and R₆ are each independently a phenyl group which may have a substituent.

5. The electrophotographic photosensitive member according to claim 4, wherein, in said Formula (1), R₄ and R₆ are each independently a phenyl group substituted with at least one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an iodine atom, a nitro group, a trifluoromethyl group, a trifluoromethoxyl group, an acetyl group and a cyano group.

6. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), A₁, A₂ and A₃ are each independently a group selected from the group consisting of groups represented by formulas in the following Formula (2):

7. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), n₁, n₂ and n₃ are 0.

8. The electrophotographic photosensitive member according to claim 7, wherein, in said Formula (1), R₃ and R₅ are each a hydrogen atom, R₄ and R₆ are each independently a phenyl group substituted with at least one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an iodine atom, a nitro group, a trifluoromethyl group, a trifluoromethoxyl group, an acetyl group and a cyano group, and Z₁ and Z₂ are each an oxygen atom.

9. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), n₁ is 1 and n₂ and n₃ are each 0, and A₁ is a group selected from the group consisting of groups represented by formulas in the following Formula (2):

10. The electrophotographic photosensitive member according to claim 9, wherein, in said Formula (1), A₁ is a group represented by the following Formula (3):

11. The electrophotographic photosensitive member according to claim 9, wherein, in said Formula (1), A₁ is a group represented by the following Formula (4):

12. The electrophotographic photosensitive member according to claim 9, wherein, in said Formula (1), A₁ is a group represented by the following Formula (5):

13. The electrophotographic photosensitive member according to claim 9, wherein, in said Formula (1), R₃ and R₅ are each a hydrogen atom, R₄ and R₆ are each independently a phenyl group substituted with at least one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an iodine atom, a nitro group, a trifluoromethyl group, a trifluoromethoxyl group, an acetyl group and a cyano group, and Z₁ and Z₂ are each an oxygen atom.

14. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), n₁ and n₂ are each 1 and n₃ is 0, and A₁ and A₂ are each independently a group selected from the group consisting of groups represented by formulas in the following Formula (2):

15. The electrophotographic photosensitive member according to claim 14, wherein, in said Formula (1), A₁ is a group represented by the following Formula (3) and A₂ is a group represented by the following Formula (4):

16. The electrophotographic photosensitive member according to claim 14, wherein, in said Formula (1), A₁ is a group represented by the following Formula (6) and A₂ is a group represented by the following Formula (4):

17. The electrophotographic photosensitive member according to claim 14, wherein, in said Formula (1), R₃ and R₅ are each a hydrogen atom, R₄ and R₆ are each independently a phenyl group susbstituted with at least one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an iodine atom, a nitro group, a trifluoromethyl group, a trifluoromethoxyl group, an acetyl group and a cyano group, and Z₁ and Z₂ are each an oxygen atom.

18. The electrophotographic photosensitive member according to claim 1, wherein, in said Formula (1), n₁, n₂ and n₃ are each 1, A₁, A₂ and A₃ are each independently a group selected from the group consisting of groups represented by formulas in the following Formula (2):

19. The electrophotographic photosensitive member according to claim 18, wherein, in said Formula (1), A₁ and A₂ are each a group represented by the following Formula (3), and A₃ is a group represented by the following Formula (4):

20. The electrophotographic photosensitive member according to claim 18, wherein, in said Formula (1), R₃ and R₅ are each a hydrogen atom, R₄ and R₆ are each independently a phenyl group substituted with at least one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an iodine atom, a nitro group, a trifluoromethyl group, a trifluoromethoxyl group, an acetyl group and a cyano group, and Z₁ and Z₂ are each an oxygen atom.

21. The electrophotographic photosensitive member according to claim 1, wherein said bisazo pigment represented by said Formula (1) is at least one selected from the group consisting of bisazo pigments represented by the following Formulas (7) to (33):

Formula (7)

24. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to any one of claims 1 to 23, a charging means, an exposure means comprising a semiconductor laser having a wavelength of from 380 to 500 nm, a developing means and a transfer means.

25. A process cartridge comprising at least one means selected from the group consisting of the electrophotographic photosensitive member according to any one of claims 1 to 23, a charging means, a developing means and a cleaning means which are integrally supported, and is detachably mountable to the main body of an electrophotographic apparatus.

22. An electrophotographic photosensitive member comprising a support and a photosensitive layer, wherein

said photosensitive layer comprises at least one selected from the group consisting of bisazo pigments represented by the following Formulas (7) and (8):

23. An electrophotographic photosensitive member comprising a support and a photosensitive layer, wherein

said photosensitive layer comprises at least one selected from the group consisting of bisazo pigments represented by the following Formulas (11) to (21):