Electrophotographic photosensitive member

Claim 2

An electrophotographic photosensitive member having a conductive substrate, a charge generation layer, and a charge transport layer, characterized in that the charge transport layer comprises a binder and at least one hydrazone compound represented by the following general formula (1) or (2): ##STR11## wherein R 11 and R 12 independently of each other represent alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, phenyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 11 and R 12 form a 5- or 6-membered ring residue conjointly with the nitrogen atom to which they are bonded; R 13 and R 14 independently of each other represent alkyl or alkoxy; R 15 and R 16 independently of each other represent alkyl, aralkyl, aryl, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, or aryl substituted by alkyl, alkoxy, halogen or dialkylamino; and n represents an integer of 0 or 1, and ##STR12## wherein R 21 and R 22 independently of each other represent alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, phenyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 21 and R 22 form a 5- or 6-member ring residue conjointly with the nitrogen atom to which they are bonded; R 23 and R 24 independently of each other represent alkyl, aralkyl, aryl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino; and Ar 1 and Ar 2 independently of each other represent arylene or arylene substituted by alkyl, alkoxy or halogen.

Claim 3

The electrophotographic photosensitive member according to claim 1, wherein the charge transport layer is laid on the upper side of the charge generation layer.

Claim 4

The electrophotographic photosensitive member according to claim 1, wherein the binder in the charge transport layer is at least one resin selected from the group consisting of polyarylate, polysulfone, polyamide, polystyrene, acrylic resin, methacrylic resin, polyacrylonitrile resin, polyvinyl chloride resin, polyvinyl acetate resin, phenolic resin, epoxy resin, polyester resin, alkyd resin, polycarbonate, polyurethane, a copolymer of monomers constituting said resins, a copolymer of butadiene and a monomer constituting said resins, cellulose ester resin, and cellulose ether resin.

Claim 5

The electrophotographic photosensitive member according to claim 1, wherein the charge transport layer contains a photoconductive polymer.

Claim 6

The electrophotographic photosensitive member according to claim 1, wherein the charge transport layer contains 10-500 parts by weight of said hydrazone compound for each 100 parts by weight of the binder.

Claim 7

The electrophotographic photosensitive member according to claim 1, wherein the charge transport layer has a thickness of 5-30μ.

Claim 8

The electrophotographic photosensitive member according to claim 6, wherein the charge transport layer has a thickness of 8-20μ.

Claim 9

The electrophotographic photosensitive member according to claim 1, wherein the charge generation layer contains at least one charge-generating material selected from the group consisting of selenium, selenium-tellurium, pyrylium dyes or co-crystalline complexes thereof, thiapyrylium dyes or co-crystalline complexes thereof, phthalocyanine pigments, anthanthrone pigments, dibenzpyrenequinone pigments, pyranthrone pigments, trisazo pigments, disazo pigments, monoazo pigments, quinacridone pigments, asymmetric or symmetric quinocyanine pigments, squaric acid methine dyes, indigo dyes, thioindigo dyes, cadmium sulfide, and amorphous silicon.

Claim 10

The electrophotographic photosensitive member according to claim 8, wherein the charge generation layer contains a disazo pigment and a binder.

Claim 11

The electrophotographic photosensitive member according to claim 8, wherein the charge generation layer contains copper phthalocyanine and a binder.

Claim 12

The electrophotographic photosensitive member according to claim 8 wherein the charge generation layer is an amorphous silicon film.

Claim 13

The electrophotographic photosensitive member according to claim 1, wherein n in the general formula (1) is zero.

Claim 14

The electrophotographic photosensitive member according to claim 1, wherein both R 11 and R 12 in the general formula (1) are alkyl groups of 1-4 carbon atoms.

Claim 15

The electrophotographic photosensitive member according to claim 13, wherein said alkyl groups are each methyl or ethyl.

Claim 16

The electrophotographic photosensitive member according to claim 1, wherein both R 11 and R 12 in the general formula (1) are phenyl groups.

Claim 17

The electrophotographic photosensitive member according to claim 1, wherein both R 13 and R 14 in the general formula (1) are alkyl groups of 1-4 carbon atoms.

Claim 18

The electrophotographic photosensitive member according to claim 16, wherein said alkyl groups are each methyl or ethyl.

Claim 19

The electrophotographic photosensitive member according to claim 1, wherein both R 13 and R 14 in the general formula (1) are alkoxy groups of 1-4 carbon atoms.

Claim 20

The electrophotographic photosensitive member according to claim 18, wherein said alkoxy groups are each methoxy or ethoxy.

Claim 21

The electrophotographic photosensitive member according to claim 1, wherein both R 15 and R 16 in the general formula (1) are aryl or aryl substituted by alkyl, alkoxy, halogen or dialkylamino groups.

Claim 22

The electrophotographic photosensitive member according to claim 1, wherein both R 21 and R 22 in the general formula (2) are alkyl groups of 1-4 carbon atoms.

Claim 23

The electrophotographic photosensitive member according to claim 21, wherein said alkyl groups are each methyl or ethyl.

Claim 24

The electrophotographic photosensitive member according to claim 1, wherein both R 21 and R 22 in the general formula (2) are phenyl groups.

Claim 25

The electrophotographic photosensitive member according to claim 1, wherein Ar 1 in the general formula (2) is phenylene or phenylene substituted by alkyl, alkoxy or halogen.

Claim 26

The electrophotographic photosensitive member according to claim 1, wherein Ar 2 in the general formula (2) is phenylene or phenylene substituted by alkyl, alkoxy or halogen.

Claim 27

An electrophotographic photosensitive member having a conductive substrate and a photosensitive layer, characterized in that the photosensitive layer comprises a binder, a charge-generating material, and at least one hydrazone compound represented by the following general formula (1) or (2): ##STR13## wherein R 11 and R 12 independently of each other represent alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, phenyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 11 and R 12 form a 5- or 6-membered ring residue conjointly with the nitrogen atom to which they are bonded; R 13 and R 14 independently of each other represent alkyl or alkoxy; R 15 and R 16 independently of each other represent alkyl, aralkyl, aryl, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, or aryl substituted by alkyl, alkoxy, halogen or dialkylamino; and n represents an integer of 0 l or 1, and ##STR14## wherein R 21 and R 22 independently of each other represents alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 21 and R 22 form a 5- or 6-member ring residue conjointly with the nitrogen atom to which they are bonded; R 23 and R 24 independently of each other represent alkyl, aralkyl, aryl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino or aryl substituted by alkyl, aralkyl, halogen or dialkylamino; and Ar 1 and Ar 2 independently of each other represent arylene or arylene substituted by alkyl, alkoxy or halogen.

Claim 28

An electrophotographic photosensitive member having a conductive substrate and a photosensitive layer, characterized in that the photosensitive layer comprises a binder, a charge-generating material, and at least one hydrazone compound represented by the following general formula (1) or (2): ##STR13## wherein R 11 and R 12 independently of each other represent alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, phenyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 11 and R 12 form a 5- or 6-membered ring residue conjointly with the nitrogen atom to which they are bonded; R 13 and R 14 independently of each other represent alkyl or alkoxy; R 15 and R 16 independently of each other represent alkyl, aralkyl, aryl, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, or aryl substituted by alkyl, alkoxy, halogen or dialkylamino; and n represents an integer of 0 l or 1, and ##STR14## wherein R 21 and R 22 independently of each other represents alkyl, aralkyl, phenyl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino, or R 21 and R 22 form a 5- or 6-member ring residue conjointly with the nitrogen atom to which they are bonded; R 23 and R 24 independently of each other represent alkyl, aralkyl, aryl, alkyl substituted by alkoxy, halogen or dialkylamino, aralkyl substituted by alkyl, alkoxy, halogen or dialkylamino or aryl substituted by alkyl, aralkyl, halogen or dialkylamino; and Ar 1 and Ar 2 independently of each other represent arylene or arylene substituted by alkyl, alkoxy or halogen.

Claim 29

The electrophotographic photosensitive member according to claim 26, wherein the photosensitive layer contains a photoconductive polymer.

Claim 30

The electrophotographic photosensitive member according to claim 26, wherein the charge-generating material is at least one compound selected from the group consisting of pyrylium dyes or co-crystalline complexes thereof, thiapyrylium dyes or co-crystalline complexes thereof, phthalocyanine pigments, anthonthrone pigments, dibenzpyrenequinone pigments, pyranthrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo pigments, quinacridone pigments, asymmetric or symmetric quinocyanine, cadmium sulfide, and squaric acid methine dyes.

Claim 31

The electrophotographic photosensitive member according to claim 28, wherein the charge-generating material is a disazo pigment.

Claim 32

The electrophotographic photosensitive member according to claim 26, wherein the binder is at least one resin selected from the group consisting of polyarylate, polysulfone, polyamide, polystyrene, acrylic resin, methacrylic resin, polyacrylonitrile resin, polyvinyl chloride resin, polyvinyl acetate resin, phenolic resin, epoxy resin, polyester resin, alkyd resin, polycarbonate, polyurethane, a copolymer of monomers constituting said resins, a copolymer of butadiene and a monomer constituting said resins, cellulose ester resin, and cellulose ether resin.

Claim 33

The electrophotographic photosensitive member according to claim 26, wherein n in the general formula (1) is zero.

Claim 34

The electrophotographic photosensitive member according to claim 26, wherein both R 11 and R 12 in the general formula (1) are alkyl groups of 1-4 carbon atoms.

Claim 35

The electrophotographic photosensitive member according to claim 32, wherein said alkyl groups are each methyl or ethyl.

Claim 36

The electrophotographic photosensitive member according to claim 26, wherein both R 11 and R 12 in the general formula (1) are phenyl groups.

Claim 37

The electrophotographic photosensitive member according to claim 26, wherein both R 13 and R 14 in the general formula (1) are alkyl groups of 1-4 carbon atoms.

Claim 38

The electrophotographic photosensitive member according to claim 35, wherein said alkyl groups are each methyl or ethyl.

Claim 39

The electrophotographic photosensitive member according to claim 26, wherein both R 13 and R 14 in the general formula (1) are alkoxy groups of 1-4 carbon atoms.

Claim 40

The electrophotographic photosensitive member according to claim 37, wherein said alkoxy groups are each methoxy or ethoxy.

Claim 41

The electrophotographic photosensitive member according to claim 26, wherein both R 15 and R 16 in the general formula (1) are aryl or aryl substituted by alkyl, alkoxy, halogen or dialkylamino groups.

Claim 42

The electrophotographic photosensitive member according to claim 26, wherein both R 21 and R 22 in the general formula (2) are alkyl groups of 1-4 carbon atoms.

Claim 43

The electrophotographic photosensitive member according to claim 40, wherein said alkyl groups are each methyl or ethyl.

Claim 44

The electrophotographic photosensitive member according to claim 26, wherein both R 21 and R 22 in the general formula (2) are phenyl groups.

Claim 45

The electrophotographic photosensitive member according to claim 26, wherein Ar 1 in the general formula (2) is phenylene or phenylene substituted by alkyl, alkoxy or halogen.

Claim 46

The electrophotographic photosensitive member according to claim 26, wherein Ar 2 in the general formula (2) is phenylene or phenylene substituted by alkyl, alkoxy or halogen.