US 8,524,429 B2Granted

Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

AssigneeCanon Kabushiki Kaishi

InventorsKunihiko Sekido, Hideaki Nagasaka, Michiyo Sekiya, Shinji Takagi

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Abstract

The present invention relates to an electrophotographic photosensitive member obtained by providing an intermediate layer and a photosensitive layer on a conductive support in the stated order, the electrophotographic photosensitive member being characterized in that the intermediate layer contains a specific polyolefin resin and a specific organic electron-transporting substance, and a process cartridge and an electrophotographic apparatus each having the electrophotographic photosensitive member.

Claims5

Dependent claims

An electrophotographic photosensitive member, comprising:

a conductive support;
an intermediate layer;
and
a photosensitive layer,
the intermediate layer and the photosensitive layer being provided on the conductive support in the stated order,
wherein:
the intermediate layer contains a polyolefin resin and an organic electron- transporting substance;
the polyolefin resin comprises:
a repeating structural unit represented by the following formula (11);
a repeating structural unit represented by one of the following formulas (21) and (22);
and
a repeating structural unit represented by any one of the following formulas (31), (32), (33), and (34), and
the mass ratio (%) of the repeating structural unit represented by the formula (11) in the polyolefin resin is 75 mass % or more and 94 mass % or less;
and
the organic electron-transporting substance comprises a compound selected from the group consisting of an imide-based compound represented by the following formula (1), a benzimidazole-based compound represented by the following formula (2), a benzimidazole-based compound represented by the following formula (3), a benzimidazole-based compound represented by the following formula (4), a quinone-based compound represented by the following formula (5), a quinone-based compound represented by the following formula (6), a quinone-based compound represented by the following formula (7), a cyclopentadienylidene-based compound represented by the following formula (8), and derivatives of the compounds:
where R11 to R14 each independently represent a hydrogen atom or an alkyl group;
where R21 to R24 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or a monovalent group represented by —Y21COOH where Y21 represents a single bond, an alkylene group, or an arylene group, R25 and R26 each independently represent a hydrogen atom, an alkyl group, or a phenyl group, and X21 represents a divalent group represented by —Y22COOCOY23—where Y22 and Y23 each independently represent a single bond, an alkylene group, or an arylene group, provided that at least one of R21 to R24 represents a monovalent group represented by —Y21COOH;
where, in the formulas (31) to (34), R31 to R35 each independently represent a hydrogen atom or a methyl group, R41 to R43 each independently represent an alkyl group having 1 to 10 carbon atoms, and R51 to R53 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
where, in the formula (1), R1 and R2 each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and n represents 1;
where, in the formula (2), R3 to R6 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a halogen group, n represents 1;
where, in the formula (3), R7 to R10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a halogen group, n represents 1;
where, in the formula (4), R11 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a halogen group, or a nitro group, R13 represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and n represents 1;
where, in the formula (5), R14 to R21 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group, or two arbitrary adjacent groups of R's (R14 to R21) may be bonded to each other so as to be cyclic;
where, in the formula (6), R31 represents an oxygen atom or a dicyanomethylene group, R32 to R39 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a halogen group, or a nitro group, X2 represents a carbon atom or a nitrogen atom, and, when X2 represents a nitrogen atom, neither R35 nor R36 is present;
where, in the formula (7), R40 represents an oxygen atom or a dicyanomethylene group, R41 to R48 each independently represent a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen group, or a substituted or unsubstituted alkyl group, X3 represents a carbon atom or a nitrogen atom, and, when X3 represents a nitrogen atom, neither R43 nor R47 is present;
and
where, in the formula (8), R22 represents an oxygen atom, a dicyanomethylene group, or an anilidene group, the anilidene group may have an alkyl group, R23 to R30 each independently represent a hydrogen atom, an ester group, or a nitro group, X1 represents a carbon atom or a nitrogen atom, and, when X1 represents a nitrogen atom, neither R26 nor R27 is present.

24 more elements

Dependencies are inferred from the claim text.

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Abstract

An electrophotographic photosensitive member, comprising:

a conductive support;
an intermediate layer;
and
a photosensitive layer,
the intermediate layer and the photosensitive layer being provided on the conductive support in the stated order,
wherein:
the intermediate layer contains a polyolefin resin and an organic electron- transporting substance;
the polyolefin resin comprises:
a repeating structural unit represented by the following formula (11);
a repeating structural unit represented by one of the following formulas (21) and (22);
and
a repeating structural unit represented by any one of the following formulas (31), (32), (33), and (34), and
the mass ratio (%) of the repeating structural unit represented by the formula (11) in the polyolefin resin is 75 mass % or more and 94 mass % or less;
and
the organic electron-transporting substance comprises a compound selected from the group consisting of an imide-based compound represented by the following formula (1), a benzimidazole-based compound represented by the following formula (2), a benzimidazole-based compound represented by the following formula (3), a benzimidazole-based compound represented by the following formula (4), a quinone-based compound represented by the following formula (5), a quinone-based compound represented by the following formula (6), a quinone-based compound represented by the following formula (7), a cyclopentadienylidene-based compound represented by the following formula (8), and derivatives of the compounds:
where R11 to R14 each independently represent a hydrogen atom or an alkyl group;
where R21 to R24 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or a monovalent group represented by —Y21COOH where Y21 represents a single bond, an alkylene group, or an arylene group, R25 and R26 each independently represent a hydrogen atom, an alkyl group, or a phenyl group, and X21 represents a divalent group represented by —Y22COOCOY23—where Y22 and Y23 each independently represent a single bond, an alkylene group, or an arylene group, provided that at least one of R21 to R24 represents a monovalent group represented by —Y21COOH;
where, in the formulas (31) to (34), R31 to R35 each independently represent a hydrogen atom or a methyl group, R41 to R43 each independently represent an alkyl group having 1 to 10 carbon atoms, and R51 to R53 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
where, in the formula (1), R1 and R2 each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and n represents 1;
where, in the formula (2), R3 to R6 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a halogen group, n represents 1;
where, in the formula (3), R7 to R10 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a halogen group, n represents 1;
where, in the formula (4), R11 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a halogen group, or a nitro group, R13 represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and n represents 1;
where, in the formula (5), R14 to R21 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group, or two arbitrary adjacent groups of R's (R14 to R21) may be bonded to each other so as to be cyclic;
where, in the formula (6), R31 represents an oxygen atom or a dicyanomethylene group, R32 to R39 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a halogen group, or a nitro group, X2 represents a carbon atom or a nitrogen atom, and, when X2 represents a nitrogen atom, neither R35 nor R36 is present;
where, in the formula (7), R40 represents an oxygen atom or a dicyanomethylene group, R41 to R48 each independently represent a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen group, or a substituted or unsubstituted alkyl group, X3 represents a carbon atom or a nitrogen atom, and, when X3 represents a nitrogen atom, neither R43 nor R47 is present;
and
where, in the formula (8), R22 represents an oxygen atom, a dicyanomethylene group, or an anilidene group, the anilidene group may have an alkyl group, R23 to R30 each independently represent a hydrogen atom, an ester group, or a nitro group, X1 represents a carbon atom or a nitrogen atom, and, when X1 represents a nitrogen atom, neither R26 nor R27 is present.

24 more elements