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EP0220604A2 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0220604A2
EP0220604A2 EP86114250A EP86114250A EP0220604A2 EP 0220604 A2 EP0220604 A2 EP 0220604A2 EP 86114250 A EP86114250 A EP 86114250A EP 86114250 A EP86114250 A EP 86114250A EP 0220604 A2 EP0220604 A2 EP 0220604A2
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EP
European Patent Office
Prior art keywords
layer
recording material
charge
parts
compound
Prior art date
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Granted
Application number
EP86114250A
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German (de)
English (en)
Other versions
EP0220604B1 (fr
EP0220604A3 (en
Inventor
Wolfgang Dr. Wiedemann
Jürgen Fürderer
Michael Drexler
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Hoechst AG
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Hoechst AG
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Publication of EP0220604A3 publication Critical patent/EP0220604A3/de
Application granted granted Critical
Publication of EP0220604B1 publication Critical patent/EP0220604B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0605—Carbocyclic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0698—Compounds of unspecified structure characterised by a substituent only
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/07—Polymeric photoconductive materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
    • Y10S430/10—Donor-acceptor complex photoconductor

Definitions

  • the invention relates to an electrophotographic recording material, consisting of an electrically conductive layer support and a photoconductive system applied thereon, optionally consisting of an insulating intermediate layer and a layer with a charge carrier-producing compound and a layer with charge-transporting compound in a mixture with binders, sensitizers, acceptors and conventional additives.
  • sensitizers and acceptors in particular in a photoconductive double-layer arrangement, is known (DE-PS 11 27 218 corresponding to US Pat. No. 3,287,123, DE-AS 15 72 347 corresponding to US Pat. No. 3,484,237 or DE-PS 22 20 408 corresponding to US -PS 3,973,959).
  • DE-OS 33 31 592 corresponding to GB-PS 2,130,597, describes photoconductive layers which may contain sensitizers, such as methyl violet, rhodamine B, and acceptors, such as tetracyanoethylene or chloranil; they often form charge transfer complexes colored with the charge-transporting compounds, which can lead to undesired increased dark conductivity and unstable charging behavior.
  • sensitizers such as methyl violet, rhodamine B
  • acceptors such as tetracyanoethylene or chloranil
  • EP-OS 0 069 397 describes photoconductive double layers which contain certain dicyanovinyl compounds in the transport layer as acceptors.
  • EP-PS 0 058 084 describes a sensitizer of the nitrophthalic anhydride type which is suitable for activating monodisperse photoconductive layers with phthalocyanine derivatives and polyester resins.
  • the object of the present invention is to improve the residual discharge behavior and the cyclic behavior of photoconductive systems in a double-layer arrangement without the other good electrophotographic parameters, such as the pre-exposure insensitivity or the charge acceptance, being significantly influenced.
  • the compounds of the general formula according to the invention are preferably used in an amount of 0.5 to 6 percent by weight, based on the total coating.
  • the acceptor additives according to the invention bring about a reduction in the residual discharge and also an improved constancy of the cyclic parameters in the photoconductive system without the other good electrophotographic properties, such as photosensitivity, charge acceptance, dark decay, etc., being impaired.
  • the acceptor additives are preferably contained in the charge transport layer. However, it could also be demonstrated that, when added alone to the precoating in contact with the charge-generating layer, they also significantly improve the electrophotographic properties.
  • Position 1 indicates the electrically conductive layer support
  • position 2 indicates the layer generating the charge carrier
  • position 3 indicates the layer carrying the charges
  • Position 4 represents the insulating intermediate layer which may be present
  • position 5 represents layers which form a charge carrier-generating layer as a pigment layer in dispersion, for example hint with a binder.
  • Aluminum foil optionally transparent, aluminum-vapor-coated, sputtered or aluminum-clad polyester foil, is preferably used as the electrically conductive layer support, however, any other support material made sufficiently conductive (for example by carbon black, metal powder, etc.) can also be used.
  • the photoconductive system can also be arranged on a drum, on flexible endless belts, for example made of nickel or steel, etc., or on plates (for example made of aluminum).
  • an insulating intermediate layer optionally also a thermally, anodically or chemically produced aluminum oxide intermediate layer (FIG. 2, position 4), has the aim of reducing the charge carrier injection from the metal into the photoconductor layer in the dark. On the other hand, it should not hinder the flow of charge during the exposure process.
  • the intermediate layer acts as a barrier layer; it may also serve to improve the adhesion between the substrate surface and the dye layer or photoconductor layer.
  • Synthetic resin binders are used, but preference is given to using materials which adhere well to a metal, in particular aluminum surface, and which are slightly dissolved when subsequent layers are applied. These include polyamide resins, polyvinyl alcohols, polyvinylphosphonic acid, polyurethanes, polyester resins, furthermore polycarbonates, phenoxy resins, cellulose nitrates, PVC-PVAc copolymers, also copolymers of styrene and butadiene, (meth) acrylic acid esters and maleic anhydride. Additions of the acceptor additives according to the invention to the precoating improve the electrophotographic behavior.
  • the thickness of organic intermediate layers can be up to 5 ⁇ m, that of an aluminum oxide intermediate layer is generally in the range of 0.01 to 1 ⁇ m.
  • Layer 2 or 5 according to the invention has the function of a layer generating charge carriers; the pigment used determines the spectral photosensitivity of the photoconductive system through its absorption behavior.
  • Pigments which are preferably used for this purpose are: perylimide derivatives, cis and trans perinones, phthalocyanines (metal-containing and free), thioindigo, dioxazine and quinacridone derivatives, and also perylene-3,4,9,10-tetracarboxylic acid bisbenzimidazole Derivatives, polynuclear quinones, e.g. 4,10-dibromoanthanthrone (C.I. 59 300), azo and bisazo dyes etc.
  • the application of a homogeneous, densely packed pigment layer is preferably obtained by evaporating the pigment onto the support in vacuo.
  • Can depending on the vacuum level, under the conditions of 1.33 10 '' to 10- 8 bar and 240 to 290 ° C heating temperature of the vapor-deposited dye without decomposition.
  • the temperature of the substrate is below 50 ° C.
  • An advantageous layer thickness range of the vapor-deposited pigment is between 0.005 and 3 ⁇ m.
  • a thickness range between 0.05 and 1.5 ⁇ m is particularly preferred since the adhesive strength and homogeneity of the vapor-deposited pigment are particularly favorable here.
  • a uniform pigment layer thickness can also be achieved by other coating techniques. This subheading includes mechanical rubbing of the finely powdered material into the electrically conductive substrate, electrolytic or electrochemical processes or electrostatic spray technology.
  • homogeneous, well covering pigment layers with thicknesses of the order of 0.05 to 3 ⁇ m can also be obtained by grinding the pigment with binder, in particular with cellulose nitrates and / or crosslinking binder systems, for example polyisocyanate-crosslinkable acrylic resins, Reactive resins, such as epoxies, DD lacquers, and by subsequently coating these dispersions according to position 5 in Figure 3 can be produced.
  • binder in particular with cellulose nitrates and / or crosslinking binder systems, for example polyisocyanate-crosslinkable acrylic resins, Reactive resins, such as epoxies, DD lacquers, and by subsequently coating these dispersions according to position 5 in Figure 3 can be produced.
  • binders such as polystyrene, styrene-maleic anhydride copolymers, polymethacrylates, polyvinyl acetates, polyurethanes, polyvinyl butyrals, polycarbonates, polyesters, phenoxy resins etc. and mixtures thereof can be used.
  • the pigment / binder ratio can vary within wide limits, but preference is given to pigment primers with a pigment content of over 50% and correspondingly high optical density; the compounds according to the invention can also be added to the dispersions.
  • Organic materials which have an extensive ⁇ -electron system are particularly suitable as the charge transport material. These include both monomeric and polymeric aromatic or heterocyclic compounds.
  • the monomers used are in particular those which have at least one tertiary nitrogen atom and / or a dialkylamino group.
  • Heterocyclic compounds such as oxdiazole derivatives, which are mentioned in German patent 10 58 836 (corresponding to US Pat. No. 3,189,447), have proven particularly useful. These include, in particular, 2,5-bis (p-diethylaminophenyl) oxdiazole-1,3,4; unsymmetrical oxdiazoles, such as 5- [3- (9-ethyl) -carbazolyl] -1,3,4-oxdiazole derivatives (US Pat. No. 4,192,677), about 2- (4-diaikyiaminophenyi -) - 5- [3 - (9-ethy)) - carbazolyl] -1,3,4-oxdiazole can be used successfully.
  • Suitable monomeric compounds are arylamine derivatives (triphenylamine) and triarylmethane derivatives (DE-PS 12 37 900), e.g. Bis (4-diethylamino-2-methylphenyl) phenylmethane, more condensed aromatic compounds such as pyrene, benzo-condensed heterocycles (e.g. benzoxazole derivatives).
  • Pyrazolines are also suitable, e.g. 1,3,5-triphenylpyrazolines or imidazole derivatives (DE-PS 10 60 714 or 11 06 599, corresponding to US-PS 3,180,729, GB-PS 938,434).
  • This subheading also includes triazole, thiadiazole and especially oxazole derivatives, for example 2-phenyl-4- (2-chlorophenyl) -5 (4-diethylaminophenyl) oxazole, as described in German patents 10 60 260, 12 99 296, 11 20,875 (corresponding to U.S. Patent 3,112,197, UK Patent 1,016,520, U.S. Patent 3,257,203).
  • polyvinyl carbazole or copolymers with at least 50% vinyl carbazole content as transport polymers provide good photosensitivity.
  • the charge-transporting layer 3 has practically no photosensitivity in the visible range (420 to 750 nm). It preferably consists of a mixture of an electron donor compound (organic photoconductor) with a binding agent if negative charging is to be carried out. It is preferably transparent, but this is not necessary in the case of a transparent, conductive layer support.
  • Layer 3 has a high electrical resistance of greater than 10 Q. It prevents the discharge of the electrostatic charge in the dark; when exposed, it transports the charges generated in the dye layer.
  • the mixing ratio of the charge transporting compound to the binder can vary. However, the requirement for maximum photosensitivity, i.e. largest possible proportion of charge-transporting compound, and after crystallization to be avoided and increased flexibility, i.e. as large a proportion of binders as possible, relatively certain limits.
  • a mixing ratio of approximately 1: 1 parts by weight has generally proven to be preferred, but ratios between 4: 1 to 1: 4 are also suitable.
  • charge-transporting compounds such as polyvinyl carbazole
  • binder proportions of around or below 30% are suitable.
  • the charge transport layer compositions are about 40 to 70% photoconductor compound, 20 to 60% binder and up to 10% of the acceptor additive.
  • the added binder influences both the mechanical behavior, such as abrasion, flexibility, film formation, adhesion, etc., and to a certain extent the electrophotographic behavior, such as photosensitivity, residual charge and cyclic behavior under normal conditions, as well as under higher conditions Temperature (20 to 50 ° C) and humidity (greater than 80% relative humidity).
  • the pre-exposure sensitivity can be increased by certain binders, such as cellulose nitrate, in certain photoconductors, such as oxdiazole derivatives.
  • polyvinyl chloride copolymers of vinyl chloride and vinyl acetate, polyvinylidene chlorides, polyacrylonitriles and cellulose nitrates can in particular also be blended with the above binders; a proportion of up to about 10 percent by weight, based on the solids content of the charge transport layer, has proven to be advantageous without the pre-exposure sensitivity increasing significantly.
  • an activating additive to the charge transport layer mixtures of polymeric and monomeric acceptor additives, e.g. Cellulose nitrate and 9,10-dibromoanthracene are present, their optical transparency should not be significantly affected.
  • the layer thickness is also important for the optimal photosensitivity of the charge transport layer: layer thicknesses between about 2 and 25 m are generally used. A thickness range of 5 to 18 3 nm has proven to be advantageous. However, if the mechanical requirements and the electrophotographic parameters (charging and development station) of a copying machine permit, the specified limits can be extended upwards or downwards in certain cases.
  • Leveling agents such as silicone oils, wetting agents, in particular nonionic substances, plasticizers of different compositions, such as, for example, those based on chlorinated hydrocarbons or those based on phthalic acid esters are considered to be customary additives.
  • An aluminum vapor-coated polyester film as a layer support is vacuum (1.33 x 10 -7 to 10 -8 bar) with the pigments N, N'-dimethylperylimide (formula 1 of the attached formula table) and N, N'-di (3-methoxipropyl ) gently vaporized perylimide (formula 2) in the temperature range from 270 to 290 ° C; the layer thicknesses of the homogeneous pigment layers are approximately 120 and 190 mg / m 2 .
  • a solution of equal parts by weight of 2,5-bis (4-dialkylaminophenyl) -oxdiazole-1,3,4 (To 1920) and polyester resin (Dynapol L L 206) in tetrahydrofuran is applied and dried to a thickness of 9 to 10 ⁇ m .
  • a coating solution is prepared as above, in which 10 percent by weight of the polyester resin is replaced by low-viscosity cellulose nitrate (standard type HP 10) (CN), and is spun onto the pigment vapor deposition layers in a thickness of 9 to 10 ⁇ m (dry).
  • the sample is moved through a charging device to the exposure station, where it is continuously exposed to a tungsten halogen lamp (150 W).
  • a heat absorption glass and a neutral filter are installed upstream of the lamp.
  • the light intensity in the measuring plane is in the range from 3 to 10 ⁇ W / cm 2 ; it is measured in parallel with the measuring process with an optometer.
  • the charge level and the photo-induced light decay curve are recorded by an electrometer using a transparent probe.
  • the photoconductor layer is characterized by the charge level (U o ) and the time (T) required to reach half, a quarter and an eighth of the original charge (U o ).
  • the residual charge U E measured primarily after 1 or 3 s, is also a measure of the residual discharge behavior.
  • a solution of 50 parts of To 1920, 40 parts of polycarbonate (Makrolon R 2405) and 10 parts of polyester resin (Dynapol L 206) in tetrahydrofuran is spun onto a thin pigment vapor deposition layer of N, N'-dimethylperylimide according to Example 1 and spun to about 10 ⁇ m Thickness dried (O layer).
  • coating solutions are prepared that contain 48 parts of To 1920, the same proportions of binder as above and 2 parts of acceptor compounds (see table); they are also layered onto the pigment layer in a comparable thickness and dried.
  • the photosensitivity of the O layer and the activated charge transport layers is shown in Table 1:
  • Thin N, N'-dimethylperylimide vapor deposition layers are coated with tetrahydrofuran solutions which contain different amounts of 9,10-dibromoanthracene (DBA).
  • DBA 9,10-dibromoanthracene
  • the first solution of this DBA concentration series consists of 50 parts To 1920, 39 parts polycarbonate (Makrolon 2405), 10 parts polyester resin (Dynapol L 206) and 1 part DBA, the other solutions contain 2.5, 5.0 and 10 Parts of DBA instead of polycarbonate. After drying for 5 minutes at 95 to 100 ° C, the layer thickness is about 8 microns.
  • a thin polycarbonate precoating (less than 0.1 ⁇ m) is applied to an aluminum-vapor-coated polyester film and trans-Perinon (Hostapermorange GR, formula 3 according to the formula table) is evaporated thereon homogeneously in vacuo under similar conditions as described in Example 1.
  • the layer weight of the pigment is in the range of 120 mg / m 2 .
  • a charge transport layer consisting of 60 parts of To 1920 and 40 parts of phenoxy resin is layered on it in a thickness of approx. 10 ⁇ m. Furthermore, differently activated charge transport layers are produced, in which phenoxy resin is partly replaced by 1, 2, 3 or 5 parts of cellulose nitrate (CN) of standard type H 27 with approx. 18% dioctyl phthalate.
  • N, N'-dimethylperylimide vapor deposition layer which was produced on an aluminum vapor-coated polyester film precoated with polycarbonate (less than 0.1 ⁇ m), is coated with a charge transport layer composed of 60 parts To 1920 and 40 parts phenoxy resin in a thickness of approximately 10 ⁇ m.
  • a composition of 60 parts of To 1920, 37 parts of phenoxy resin and 3 parts of acceptor compound was chosen to investigate further activating substances.
  • the photosensitivity of the differently activated layers is as follows:
  • a pigment vapor deposition layer according to Example 1 is coated with a tetrahydrofuran solution composed of equal parts by weight To 1920 and polycarbonate (Makrolon 3200) in a dry (approx. 9 to 10 .mu.m) thick (O layer). Additional layers are produced in which the charge transport layer is activated with small amounts of phthalic anhydride (PA) instead of polycarbonate. Composition and photosensitivity are shown in Table 4 (light intensity 4.1 ⁇ W / cm 2 ):
  • Aluminum-coated polyester film is coated with a thin adhesion-promoting layer made of polycarbonate in a thickness of ⁇ 0.1 ⁇ m (dry).
  • the pigments cis-perinone (Novopermrot TG 02, according to formula 4), perylene-3,4,9,10-tetracarboxylic acid diimidebisbenzimidazole (formula 5) and 4,10-dibromoanthanthrone (Hostapermscharlach GO, formula 6) are then vacuumed (1, 33 ⁇ 10 -7 to 10- 8 bar) gently evaporated.
  • the layer thicknesses of the homogeneous pigment vapor deposition layers are in the range from 100 to 140 mg / m '.
  • coating solutions are layered homogeneously on a pigment vapor deposition layer according to Example 1 (formula 1) by flow application in a coating machine and dried.
  • An aluminum-coated polyester film which was coated with a thin pre-coating of polycarbonate (less than 100 mg / m 2 ) (dry) and then vapor-coated homogeneously with N, N'-dimethylperylimide (approx. 130 mg / m 2 ), was used with a Solution of 98 parts of polyvinyl carbazole (Luvican R M 170) and 2 parts of polyester resin (Adhesive R 49000) coated in a thickness of approx. 6 ⁇ m after drying. By adding 1 part and 3 parts of 9,10-dibromoanthracene, the charge transport layer was activated at a layer thickness of approximately 6 ⁇ m.
  • charge carrier generation systems are uniformly coated with a tetrahydrofuran solution composed of 52 parts of To 1920 and 48 parts of phenoxy resin and a layer weight of 13.5 g / m * each.
  • the photosensitivity according to Example 1 is as follows:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP86114250A 1985-10-25 1986-10-15 Matériau d'enregistrement électrophotographique Expired - Lifetime EP0220604B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853537979 DE3537979A1 (de) 1985-10-25 1985-10-25 Elektrophotographisches aufzeichnungsmaterial
DE3537979 1985-10-25

Publications (3)

Publication Number Publication Date
EP0220604A2 true EP0220604A2 (fr) 1987-05-06
EP0220604A3 EP0220604A3 (en) 1990-02-07
EP0220604B1 EP0220604B1 (fr) 1994-03-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP86114250A Expired - Lifetime EP0220604B1 (fr) 1985-10-25 1986-10-15 Matériau d'enregistrement électrophotographique

Country Status (4)

Country Link
US (1) US4818653A (fr)
EP (1) EP0220604B1 (fr)
JP (1) JPS62100759A (fr)
DE (2) DE3537979A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5085960A (en) * 1988-05-16 1992-02-04 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
US5153085A (en) * 1988-10-05 1992-10-06 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
JPH02176665A (ja) * 1988-12-28 1990-07-09 Canon Inc 電子写真感光体
US5128226A (en) * 1989-11-13 1992-07-07 Eastman Kodak Company Electrophotographic element containing barrier layer
JPH06118668A (ja) * 1992-10-07 1994-04-28 Minolta Camera Co Ltd 感光体

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FR2117342A5 (fr) * 1970-12-03 1972-07-21 Kalle Ag
DE2108984A1 (de) * 1971-02-24 1972-08-31 Xerox Corp Elektrophotographische Platte sowie deren Verwendung
US4082550A (en) * 1977-05-25 1978-04-04 Eastman Kodak Company Hexachlorocyclopentene chemical sensitizers for heterogeneous organic photoconductive compositions
EP0058084A1 (fr) * 1981-02-09 1982-08-18 Mita Industrial Co. Ltd. Composition photosensible pour l'électrophotographie sensibilisée à la lumière
JPS59157651A (ja) * 1983-02-28 1984-09-07 Mita Ind Co Ltd 電子写真感光剤組成物

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US3121006A (en) * 1957-06-26 1964-02-11 Xerox Corp Photo-active member for xerography
US3640708A (en) * 1970-09-09 1972-02-08 Eastman Kodak Co Barrier layers for electrophotographic elements containing a blend of cellulose nitrate with a tetrapolymer having vinylidene chloride as the major constituent
US3928034A (en) * 1970-12-01 1975-12-23 Xerox Corp Electron transport layer over an inorganic photoconductive layer
DE2242595C2 (de) * 1972-08-30 1982-06-09 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
US4052205A (en) * 1975-09-24 1977-10-04 Xerox Corporation Photoconductive imaging member with substituted anthracene plasticizer
US4106934A (en) * 1976-06-14 1978-08-15 Eastman Kodak Company Photoconductive compositions and elements with charge transfer complexes
DE2737516C3 (de) * 1976-08-23 1981-09-17 Ricoh Co., Ltd., Tokyo Elektrophotographisches Aufzeichnungsmaterial
US4047948A (en) * 1976-11-01 1977-09-13 Xerox Corporation Composite layered imaging member for electrophotography
JPS5410738A (en) * 1977-06-27 1979-01-26 Ricoh Co Ltd Laminated type zerographic photosensitive material
DE2734288C2 (de) * 1977-07-29 1982-06-03 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
JPS5614240A (en) * 1979-07-16 1981-02-12 Konishiroku Photo Ind Co Ltd Electrophotographic receptor
JPS5984247A (ja) * 1982-11-05 1984-05-15 Fuji Photo Film Co Ltd 電子写真用感光材料

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2117342A5 (fr) * 1970-12-03 1972-07-21 Kalle Ag
DE2108984A1 (de) * 1971-02-24 1972-08-31 Xerox Corp Elektrophotographische Platte sowie deren Verwendung
US4082550A (en) * 1977-05-25 1978-04-04 Eastman Kodak Company Hexachlorocyclopentene chemical sensitizers for heterogeneous organic photoconductive compositions
EP0058084A1 (fr) * 1981-02-09 1982-08-18 Mita Industrial Co. Ltd. Composition photosensible pour l'électrophotographie sensibilisée à la lumière
JPS59157651A (ja) * 1983-02-28 1984-09-07 Mita Ind Co Ltd 電子写真感光剤組成物

Non-Patent Citations (1)

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Title
PATENT ABSTRACTS OF JAPAN, Band 9, Nr. 9 (P-327)[1732], 16. Januar 1985; & JP-A-59 157 651 (MITA KOGYO K.K.) 07-09-1984 *

Also Published As

Publication number Publication date
US4818653A (en) 1989-04-04
EP0220604B1 (fr) 1994-03-30
DE3689750D1 (de) 1994-05-05
EP0220604A3 (en) 1990-02-07
DE3537979A1 (de) 1987-04-30
JPS62100759A (ja) 1987-05-11

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