US4338388A
Expired / Lapsed
US
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Electrophotographic element with a phenyhydrazone charge transport layer
Assignee: Ricoh Co Ltd
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Filing: 1979-10-10
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Granted: 1982-07-06
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Expires: 1999-10-10
Abstract
Abstract An electrophotographic element is prepared by forming a photoconductive layer containing a hydrazone compound therein on an electroconductive support member. The hydrazone compounds represented by the following general formula, are useful as photoconductive materials and as charge transport materials for use in electrophotography: ##STR1## wherein Ar represents a substituted or unsubstituted condensed polycyclic group or heterocyclic group, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group. The condensed polycyclic group includes a naphthalene ring, and an anthracene ring. The heterocyclic ring includes nitrogen, oxygen and sulfur.
Inventors
- 👤 Kiyoshi Sakai
- 👤 Mitsuru Hashimoto
- 👤 Tomiko Kawakami
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:43
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0622; G03G5/0624; G03G5/0635; G03G5/0637; G03G5/0601; G03G5/0612; G03G5/0616
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
66 words
An electrophotographic element comprising: an electroconductive support member, a charge carrier producing layer, a charge transport layer adjacent the charge carrier producing layer, the charge transport layer comprising a hydrazone of the formula; ##STR49## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a binder agent.
Claim 2
Dependent Claim
66 words
An electrophotographic element comprising: an electroconductive support member, a charge carrier producing layer, a charge transport layer adjacent the charge carrier producing layer, the charge transport layer comprising a hydrazone of the formula; ##STR49## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a binder agent.
Claim 3
Dependent Claim
47 words
An electrophotographic element as claimed in claim 1, wherein said charge transport layer comprises a hydrazone selected from the group consisting of: 1-naphthalenecarbaldehyde 1-methyl-1-phenylhydrazone; 1-naphthalenecarbaldehyde 1,1-diphenylhydrazone; 4-methoxynaphthalene-1-carbaldehyde 1-methyl-1-phenylhydrazone; 4-methoxynaphthalene-1-carbaldehyde 1,1-diphenylhydrazone; 2-methoxynaphthalene-1-carbaldehyde 1,1-diphenylhydrazone; 2-methoxynaphthalene-1-carbaldehyde 1-methyl-1-phenylhydrazone; 2-methoxynaphthalene-1-carbaldehyde 1-methyl-1-phenylhydrazone; 2-methoxynaphthalene-1-carbaldehyde 1-benzyl-1-phenylhydrazone; 2-naphthalenecarbaldehyde 1-methyl-1-phenylhydrazone; 2-naphthalenecarbaldehyde 1-ethyl-1-phenylhydrazone; 9-anthracenecarbaldehyde 1-methyl-1-phenylhydrazone; and 9-anthracenecarbaldehyde 1-ethyl-1-phenylhydrazone.
Claim 4
Dependent Claim
16 words
An electrophotographic element as claimed in claim 1, wherein said charge transport layer includes 4-methoxynaphthalene-1-carbaldehyde 1-methyl-1-phenylhydrazone.
Claim 5
Dependent Claim
39 words
An electrophotographic element as claimed in claim 1, wherein said charge carrier producing layer is positioned between said electroconductive support member and said charge transport layer, with said charge transport layer forming an exposed surface of said electrophotographic element.
Claim 6
Dependent Claim
39 words
An electrophotographic element as claimed in claim 1, wherein said charge carrier producing layer is of a thickness between 0.04 μm to 5 μm, and said charge transport layer is of a thickness between 3 μm to 50 μm.
Claim 7
Dependent Claim
34 words
An electrophotographic element as claimed in claim 1 in which said charge carrier producing layer includes a photoconductive material selected from the group consisting of selenium and its alloys, azo pigment, and perylene pigment.
Claim 8
Dependent Claim
36 words
An electrophotographic element as claimed in claim 1 in which said binder agent is selected from the group consisting of polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate, polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, polyacrylamide, polyacrylate and mixtures thereof.
Claim 9
Dependent Claim
21 words
An electrophotographic element as claimed in claim 5, wherein said charge transport layer is between 5 μm to 20 μm thick.
Claim 10
Dependent Claim
77 words
An electrophotographic element as claimed in claim 6 in which said photoconductive material is a material selected from the group consisting of azo pigments having a carbazole group, azo pigments having a styrylstilbene group, azo pigments having a triphenylamine group, azo pigments having a dibenzothiophene group, azo pigments having an oxadiazole group, azo pigments having a fluorenone group, azo pigments having a bis-stilbene group, azo pigments having a distyryl-phenyloxadiazole group and azo pigments having a distyrylcarbazole group.
Claim 11
Dependent Claim
27 words
An electrophotograhic element as claimed in claim 8, wherein said photoconductive material is a material selected from the group consisting of azo pigments having a styrylstilbene group.
Claim 12
Dependent Claim
14 words
An electrophotographic element as claimed in claim 8, wherein said photoconductive material is 1,4-bis[4-{2-hydroxy-3-(2,4-dimethylphenyl)carbamoylnaphthyl-1{azostyryl-1]benzene.
Claim 13
Dependent Claim
124 words
An electrophotographic element comprising: an electroconductive support member; a charge carrier producing layer, which includes a photoconductive material selected from the group consisting of azo pigments having a carbazole group, azo pigments having a styrylstilbene group, azo pigments having a triphenylamine group, azo pigments having a dibenzothiophene group, azo pigments having an oxadiazole group, azo pigments having a fluorenone group, azo pigments having a bis-stilbene group, azo pigments having a distyryl-phenyloxadiazole group and azo pigments having a distyrylcarbazole group; and a charge transport layer, which comprises a hydrazone of the formula; ##STR50## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a binder agent.
Claim 14
Dependent Claim
124 words
An electrophotographic element comprising: an electroconductive support member; a charge carrier producing layer, which includes a photoconductive material selected from the group consisting of azo pigments having a carbazole group, azo pigments having a styrylstilbene group, azo pigments having a triphenylamine group, azo pigments having a dibenzothiophene group, azo pigments having an oxadiazole group, azo pigments having a fluorenone group, azo pigments having a bis-stilbene group, azo pigments having a distyryl-phenyloxadiazole group and azo pigments having a distyrylcarbazole group; and a charge transport layer, which comprises a hydrazone of the formula; ##STR50## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a binder agent.
Claim 15
Dependent Claim
113 words
In an electrophotographic element comprising a photoconductive layer and an electroconductive support member for supporting said photoconductive layer thereon, the improvement wherein said photoconductive layer contains a binder agent and at least a compound selected from the group consisting of hydrazone compounds represented by the general formula ##STR51## where Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group and the thickness of said photoconductive layer is in the range of 3 μm to 50 μm and the content of said hydrazone compound is in the range of 30 to 70 wt% in said photoconductive layer.
Claim 16
Dependent Claim
113 words
In an electrophotographic element comprising a photoconductive layer and an electroconductive support member for supporting said photoconductive layer thereon, the improvement wherein said photoconductive layer contains a binder agent and at least a compound selected from the group consisting of hydrazone compounds represented by the general formula ##STR51## where Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group and the thickness of said photoconductive layer is in the range of 3 μm to 50 μm and the content of said hydrazone compound is in the range of 30 to 70 wt% in said photoconductive layer.
Claim 17
Dependent Claim
73 words
An electrophotographic element as claimed in claim 13, wherein said photoconductive layer further comprises a sensitizer pigment capable of providing said photoconductive layer with a photosensitivity in the visible light range, and the content of said sensitizer pigment is in the range of 0.1 to 5 weight percent in said photoconductive layer and said sensitizer is a compound selected from the group consisting of triarylmethane dye, xanthene dye, cyanine dye, and pyrylium dye.
Claim 18
Dependent Claim
25 words
An electrophotographic element as claimed in claim 13, further comprising an adhesive layer or a barrier layer between said electroconductive layer and said photoconductive layer.
Claim 19
Dependent Claim
33 words
An electrophotographic element as claimed in claim 13, wherein said photoconductive layer further comprises a plasticizer containing a material selected from the group consisting of halogenated paraffin, polybiphenyl chloride, dimethylnaphthalene and dibutyl phthalate.
Claim 20
Dependent Claim
152 words
In an electrophotographic element comprising a photoconductive layer and an electroconductive support member for supporting said photoconductive layer thereon, the improvement wherein said photoconductive layer comprises: a charge transport medium comprising a binder agent and a compound selected from the group consisting of hydrazone compounds represented by the general formula ##STR52## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a charge carrier producing material dispersed in said charge transport medium, and the thickness of said photoconductive layer is in the range of 3 μm to 50 μm and the content of said hydrazone compound is in the range of 10 to 95 weight percent in said photoconductive layer, and the content of said charge carrier producing material is in the range of 0.1 to 50 weight percent in said photoconductive layer.
Claim 21
Dependent Claim
152 words
In an electrophotographic element comprising a photoconductive layer and an electroconductive support member for supporting said photoconductive layer thereon, the improvement wherein said photoconductive layer comprises: a charge transport medium comprising a binder agent and a compound selected from the group consisting of hydrazone compounds represented by the general formula ##STR52## wherein Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon ring system, and R represents a methyl group, an ethyl group, a benzyl group or a phenyl group; and a charge carrier producing material dispersed in said charge transport medium, and the thickness of said photoconductive layer is in the range of 3 μm to 50 μm and the content of said hydrazone compound is in the range of 10 to 95 weight percent in said photoconductive layer, and the content of said charge carrier producing material is in the range of 0.1 to 50 weight percent in said photoconductive layer.
Claim 22
Dependent Claim
21 words
An electrophotographic element as claimed in claim 1 in which Ar is selected from the group consisting of naphthalene, methoxynaphthalene anthracene.
Claim 23
Dependent Claim
33 words
An electrophotographic element as claimed in claim 5 in which said charge transport layer is free of sensitizer for said hydrazone so that said hydrazone scarcely absorbs light in the visible light range.
Claim 24
Dependent Claim
22 words
An electrophotographic element as claimed in claim 12 in which Ar is selected from the group consisting of naphthalene, methoxynaphthalene and anthracene.
Claim 25
Dependent Claim
22 words
An electrophotographic element as claimed in claim 13 in which Ar is selected from the group consisting of naphthalene, methoxynaphthalene and anthracene.
Claim 26
Dependent Claim
22 words
An electrophotograhic element as claimed in claim 17 in which Ar is selected from the group consisting of naphthalene, methoxynaphthalene and anthracene.
Claim 27
Dependent Claim
33 words
An electrophotographic element as claimed in claim 17 in which said charge transport layer is free of sensitizer for said hydrazone so that said hydrazone scarcely absorbs light in the visible light range.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-07-05 | 1986-01-04 | 1986-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-05 | 1990-01-04 | 1990-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-05 | 1994-01-04 | 1994-07-06 | $7700.00 | Window Closed / Lapsed |