EP0198488B1 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0198488B1
EP0198488B1 EP86105253A EP86105253A EP0198488B1 EP 0198488 B1 EP0198488 B1 EP 0198488B1 EP 86105253 A EP86105253 A EP 86105253A EP 86105253 A EP86105253 A EP 86105253A EP 0198488 B1 EP0198488 B1 EP 0198488B1
Authority
EP
European Patent Office
Prior art keywords
layer
electrophotographic
recording material
alkyl
ethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP86105253A
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German (de)
English (en)
Other versions
EP0198488A1 (fr
Inventor
Gerhard Dr. Hoffmann
Reinhold J. Dr. Leyrer
Peter Dr. Neumann
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BASF SE
Original Assignee
BASF SE
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Application filed by BASF SE filed Critical BASF SE
Publication of EP0198488A1 publication Critical patent/EP0198488A1/fr
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Classifications

    • 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 or 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
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/0648—Heterocyclic compounds containing two or more hetero rings in the same ring system containing two relevant rings
    • 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 or 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
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0633—Heterocyclic compounds containing one hetero ring being five-membered containing three hetero atoms

Definitions

  • a high proportion of charge transport compounds B2) is required for the correct functioning of these electrophotographic layers. Good results are only achieved if the concentration of B2) exceeds 35% by weight; often up to 50% by weight is necessary in order to be able to maintain sufficiently short exposure times, as are required today by the offset printer.
  • the present invention relates to an electrophotographic recording material which is composed of A) a conductive support and B) an electrophotographic layer of organic materials and which is characterized in that the electrophotographic layer (B) as charge transport compounds is a mixture of at least one compound of the formula and at least one compound of the formula
  • charge transport compounds are a mixture of (I) and (II), in which R 1 for ethyl, R 2 for phenyl, R 3 for 5-methoxy, R 4 for hydrogen and R 6 , R 7 , R 8 and R 9 represents ethyl.
  • the ratio of (1) to (11) is 9: 1 to 0.6: 1 parts by weight, preferably 3.5: 1 to 0.7: 1.
  • the mixture of the charge carrier transporting compounds (I) and (11) to be used according to the invention can advantageously be used both in single-layer and in multi-layered recording systems applied to aluminum sheet suitable for offset printing.
  • Suitable single-layer systems preferably have a layer (B) of (a) 65 to 35% by weight of a binder, (b) 30 to 60, in particular 38 to 46% by weight of the mixture according to the invention on a conductive carrier material (A) the charge carrier transporting compounds (I) and (11), (c) optionally up to 15% by weight of a further, essentially inactive binder and (d) 0.02 to 2.5% by weight of a charge carrier when actinically exposed producing compound, in particular a suitable dye.
  • the layers are advantageously applied to the cleaned conductive carrier material from an approximately 6% by weight solution in a suitable organic solvent in such a way that, after the solvent has been flashed off, a dry layer thickness of approximately 0.8 to 40 ⁇ m, depending on the intended use , in particular 0.8 to 6 ⁇ m in electrophotographic printing forms.
  • Suitable multilayer systems have on an electroconductive support material (A) z. B.
  • the first layer is advantageously applied to the support material in a thickness of 0.005 to 5 ⁇ m, in particular 0.1 to 0.9 ⁇ m, as a solution in a suitable solvent.
  • the second layer is applied in a thickness that results in a layer thickness of 5 to 25, in particular 7 to 15 ⁇ m, after drying the composite structure.
  • an electrically conductive carrier such. B. raw or pretreated, e.g. B. roughened and / or anodized aluminum sheets or aluminum foils with thicknesses of 0.08 to 0.6 mm into consideration.
  • suitable organic binders for the layers depends on the intended use of the recording materials.
  • their film-forming and electrical properties, their adhesive strength on the carrier material and their solubility properties play a special role.
  • Particularly suitable for recording materials for the production of electrophotographic printing plates and especially for those for offset printing are those which are soluble in basic, aqueous or alcoholic solvents.
  • binders especially those with high acid numbers, which are readily soluble in basic aqueous-alcoholic solvent systems and have an average molecular weight (weight average) of 800 to 80,000 and in particular 1,500 to 50,000.
  • binders with free carboxyl groups are known to undesirably increase the dark conductivity of the electrophotographic layers and thereby lead to poor stressing results, such binders can easily be adapted to the charge transport compounds used according to the invention. It has been shown that copolymers of styrene, maleic anhydride and acrylic or methacrylic acid, the proportion of copolymerized maleic anhydride from 5 to 50 wt .-% and a proportion of polymerized acrylic or methacrylic acid from 5 to 35, in particular 10 to 30 wt .-% have satisfactory electrophotographic layers with sufficient dark conductivity. They have excellent solubility in washing-out agents consisting of 75% by weight of water, 23% by weight of isobutanol and 2% by weight of soda, but are insoluble in offset-typical wiping water.
  • Suitable charge carrier-producing compounds or sensitizers are e.g. B. for single-layer systems, such as those used for the production of electrophotographic printing forms, dyes from the triarylmethane series, xanthene dyes and cyanine dyes. Very good results were obtained with the compounds of the formula I according to the invention and rhodamine B (CI 45170), rhodamine 6 G (CI 45160), malachite green (CI Basic Green 4; CI 42 000), methyl violet (CI 42535) or crystal violet (CI 42555) receive. In systems applied in multiple layers, the dye or pigment is present in a separate layer which generates charge carriers.
  • Azo dyes, phthalocyanines, isoindoline dyes and perylene tetracarboxylic acid derivatives are effective here. Particularly good results are achieved with perylene-3,4,9,10-tetracarboxylic acid diimide derivatives, as described in DE-OS-3 110 954 and 3 110 960.
  • the electrophotographic recording material according to the invention may contain conventional additives, e.g. B. leveling agents and plasticizers in the photoconductive layer or adhesion promoter between carrier and layer.
  • conventional additives e.g. B. leveling agents and plasticizers in the photoconductive layer or adhesion promoter between carrier and layer.
  • the materials according to the invention have clear advantages when used for the production of electrophotographic printing forms and meet high demands with regard to the resolution capacity and the print run.
  • the high sensitivity to light allows the exposure time during processing in the repro camera to be reduced by about half compared to commercially available materials.
  • a good resolution results from a very sharp image reproduction.
  • Thanks to a high charge contrast fine halftone dots can also be reproduced well in the clear tone word areas.
  • the exposure of the layers leads to very low residual stresses and the images obtained during the concreting are characterized by good basic freedom in the non-image areas. Since the spectral sensitivity of the layers drops sharply at 600 nm, the layers can be handled with red light without loss of image.
  • electrophotographic offset printing forms takes place, as usual, by electrostatically charging the electrophotographic recording material using a high-voltage corona, directly following image-wise exposure, developing the electrostatic latent charge image present using a dry or liquid toner, fixing the toner by means of a downstream melting process and the like Removal of the unstressed, photo-semiconducting layer using a suitable wash-out solvent.
  • the printing form thus obtained can be prepared in a known manner for offset printing, for. B. by hydrophilizing and gumming the water-bearing surface.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Claims (10)

1. Matériau d'enregistrement électrophotographique se composant A) d'un support conducteur et B) d'une couche électrophotographique faite de matières organiques, caractérisé en ce que la couche électrophotographique (B) contient, en tant que composés de transport de charge, un mélange d'au moins un composé de formule
Figure imgb0008
et d'au moins un composé de formule
Figure imgb0009
dans un rapport de 9 : 1 à 0,6 : 1 parties en poids, Rl et R2 dans les formules étant mis chacun, indépendamment l'un de l'autre, pour un radical alkyle en C1 à C6 allyle, phényl-C1- à -C4-alkyle ou pour un radical phényle éventuellement substitué par un groupe alkyle en C1 à C4, un groupe alcoxy en C1 à C4 et/ou un atome d'halogène, R3 et R4 étant mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène, d'halogène, un radical alkyle en C1 à C4 ou alcoxy en C1 à C4, et R6, R7, R8 et R9 étant mis chacun, indépendamment les uns des autres, pour un radical alkyle en C1 à C4, phényl-C1- ou C2-alkyle ou cyclohexyle.
2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que la couche (B) contient des composés de transport de charge de formules (1) et (II), R1 étant mis pour un radical méthyle, éthyle ou benzyle,
R2 pour un radical méthyle, éthyle ou phényle,
R3 pour un atome d'hydrogène, un radical 5-méthoxy ou 5-éthoxy,
R4 pour un atome d'hydrogène et
R6, R7, R8 et R9 étant mis chacun pour un radical méthyle, éthyle, propyle ou butyle.
3. Matériau d'enregistrement selon la revendication 2, caractérisé en ce que Rl est mis pour un radical éthyle, R2 pour un radical phényle, R3 pour un radical 5-méthoxy, R4 pour un atome d'hydrogène et R6, R7, R8 et R9 sont mis chacun pour un radical éthyle.
4. Matériau d'enregistrement selon l'une quelconque des revendications 1 à 3, caractérisé en ce que le rapport en poids des composés (1) et (II) se situe dans la gamme de 2,3 : 1 à 0,8 : 1.
5. Matériau d'enregistrement selon l'une quelconque des revendications 1 à 4, caractérisé en ce que la couche électrophotographique (B) contient 30 à 60, de préférence 38 à 46 % en poids de (1) et (II), sur la base de (B).
6. Matériau d'enregistrement selon l'une quelconque des revendications 1 à 5, caractérisé en ce que la couche électrophotographique (B) contient 0 à 5 % en poids, sur la base de (B), d'un ou de plusieurs activateurs.
7. Procédé pour la fabrication d'un matériau d'enregistrement électrophotographique se composant A) d' un support conducteur et B) d'une couche électrophotographique faite de matières organiques selon l'une quelconque des revendications 1 à 6, caractérisé en ce que la couche (B) est appliquée sur le support (A) sous forme d'une solution, au moyen d'une raclette ou d'un dispositif à rouleau.
8. Procédé selon la revendication 7, caractérisé en ce que la couche (B) est appliquée en une épaisseur de 0,8 à 40 µm, de préférence de 0,8 à 6 µm.
9. Procédé selon la revendication 7 ou 8, caractérisé en ce qu'on utilise, en tant que (A), un support en tôle convenant pour l'impression offset, de préférence un support en tôle d'aluminium rendu rugueux électriquement, oxydé anodiquement et traité par un enduit protecteur.
10. Utilisation des matériaux d'enregistrement selon l'une quelconque des revendications 1 à 6 pour l'impression offset électrophotographique.
EP86105253A 1985-04-19 1986-04-16 Matériau d'enregistrement électrophotographique Expired EP0198488B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3514182 1985-04-19
DE19853514182 DE3514182A1 (de) 1985-04-19 1985-04-19 Elektrophotographisches aufzeichnungsmaterial

Publications (2)

Publication Number Publication Date
EP0198488A1 EP0198488A1 (fr) 1986-10-22
EP0198488B1 true EP0198488B1 (fr) 1988-07-20

Family

ID=6268596

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EP86105253A Expired EP0198488B1 (fr) 1985-04-19 1986-04-16 Matériau d'enregistrement électrophotographique

Country Status (4)

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US (1) US4743521A (fr)
EP (1) EP0198488B1 (fr)
JP (1) JPH0629973B2 (fr)
DE (2) DE3514182A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3740421A1 (de) * 1987-11-28 1989-06-08 Basf Ag Mehrschichtiges, elektrophotographisches aufzeichnungsmaterial
JP2630327B2 (ja) * 1988-09-28 1997-07-16 コスモ石油株式会社 ビスカスカップリング用流体組成物
US4874682A (en) * 1988-10-28 1989-10-17 International Business Machines Corporation Organic photoconductors with reduced fatigue
US5059503A (en) * 1989-03-30 1991-10-22 Mita Industrial Co., Ltd. Electrophotosensitive material with combination of charge transfer materials
US5192633A (en) * 1989-05-09 1993-03-09 Mita Industrial Co., Ltd. Laminate type photosensitive material for electrophotography
US5261118A (en) * 1991-10-04 1993-11-09 Motorola, Inc. Simulcast synchronization and equalization system and method therefor
US5257404A (en) * 1991-10-04 1993-10-26 Motorola, Inc. Simulcast synchronization and equalization system and method therefor
US5324606A (en) * 1991-11-26 1994-06-28 Fuji Xerox Co., Ltd. Electrophotographic photoreceptor
MY151199A (en) * 2001-11-02 2014-04-30 Rigel Pharmaceuticals Inc Substituted diphenyl heterocycles useful for treating hcv infection
WO2004099164A1 (fr) * 2003-05-02 2004-11-18 Rigel Pharmaceuticals, Inc. Diphenyl isoxazoles, pyrazoles et oxadiazoles substitues, destines au traitement d'une infection par le vhc
US7326790B2 (en) * 2003-05-02 2008-02-05 Rigel Pharmaceuticals, Inc. Diphenylisoxazole compounds and hydro isomers thereof
US7220745B2 (en) * 2003-05-15 2007-05-22 Rigel Pharmaceuticals Heterocyclic compounds useful to treat HCV
US7410979B2 (en) * 2003-11-19 2008-08-12 Rigel Pharmaceuticals, Inc. Synergistically effective combinations of dihaloacetamide compounds and interferon or ribavirin against HCV infections
US7514434B2 (en) 2004-02-23 2009-04-07 Rigel Pharmaceuticals, Inc. Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof
WO2005097760A1 (fr) * 2004-03-26 2005-10-20 Rigel Pharmaceuticals, Inc. Composes antiviraux heterocycliques comportant des groupes fonctionnels metabolisables et leurs utilisations
CA2606106A1 (fr) * 2005-05-02 2007-03-08 Rigel Pharmaceuticals, Inc. Composes heterocycliques antiviraux comprenant des groupes metabolisables et leurs utilisations

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3140174A (en) * 1955-01-19 1964-07-07 Xerox Corp Process for overcoating a xerographic plate
AT204396B (de) * 1956-06-04 1959-07-10 Kalle & Co Ag Material für elektrophotographische Reproduktion
DE2949826A1 (de) * 1979-12-12 1981-06-19 Hoechst Ag, 6230 Frankfurt Material fuer elektrophotographische reproduktion
JPS5882252A (ja) * 1981-11-11 1983-05-17 Fuji Xerox Co Ltd 電子写真感光体
DE3215968A1 (de) * 1982-04-29 1983-11-03 Basf Ag, 6700 Ludwigshafen Elektrographische aufzeichnungsmaterialien mit speziellen ladungstraeger transportierenden verbindungen
DE3215967A1 (de) * 1982-04-29 1983-11-03 Basf Ag, 6700 Ludwigshafen Elektrographische aufzeichnungsmaterialien mit speziellen ladungstraeger transportierenden verbindungen

Also Published As

Publication number Publication date
JPS61243457A (ja) 1986-10-29
DE3660409D1 (en) 1988-08-25
DE3514182A1 (de) 1986-10-23
EP0198488A1 (fr) 1986-10-22
US4743521A (en) 1988-05-10
JPH0629973B2 (ja) 1994-04-20

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