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EP0218981B1 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0218981B1
EP0218981B1 EP86113419A EP86113419A EP0218981B1 EP 0218981 B1 EP0218981 B1 EP 0218981B1 EP 86113419 A EP86113419 A EP 86113419A EP 86113419 A EP86113419 A EP 86113419A EP 0218981 B1 EP0218981 B1 EP 0218981B1
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Prior art keywords
layer
charge
dye
recording material
group
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Application number
EP86113419A
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German (de)
English (en)
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EP0218981A2 (fr
EP0218981A3 (en
Inventor
Wolfgang Dr. Wiedemann
Hans M. Dr. Deger
Dieter Dr. Günther
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Hoechst AG
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Hoechst AG
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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
    • G03G5/0622—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
    • G03G5/0655—Heterocyclic compounds containing two or more hetero rings in the same ring system containing six relevant rings

Definitions

  • the invention relates to an electrophotographic recording material composed of an electrically conductive layer support, optionally an insulating intermediate layer and a photoconductive layer composed of at least one dye as a charge-generating compound, photoconductor as a charge transport compound, binders and a layer containing conventional additives.
  • the invention relates in particular to a recording material composed of an electrically conductive layer support, optionally an insulating intermediate layer, a dye layer with a dye as the charge carrier-producing compound and an organic photoconductor as the layer containing the charge transport compound.
  • the recording material according to the invention is advantageously suitable for a lithographic printing form or printed circuit which can be produced by electrophotographic means, consisting of a correspondingly suitable electrically conductive layer support and a photoconductive layer with binders which can be stripped of alkali.
  • the known dyes have good photosensitivities, which are approximately in the range from 420 to 650 nm.
  • the dyes of the invention as charge-generating compounds have excellent electrophotographic properties and, with many organic photoconductors, and especially with a wide variety of binders, give good photosensitive recording materials both in a double-layer and in a monolayer arrangement with the dye dispersed therein.
  • Position 1 indicates the electrically conductive layer support
  • position 2 indicates the dye layer generating charge carriers
  • position 3 indicates the charge transport layer
  • Position 4 specifies the insulating intermediate layer
  • position 5 shows layers which represent a charge carrier-producing dye layer in dispersion
  • Position 6 shows a photoconductive monolayer composed of disperse dye, photoconductor and binder.
  • Aluminum foil optionally transparent, aluminum-vapor-coated or aluminum-clad polyester foil, is preferably used as the electrically conductive layer support, however, any other support material made sufficiently conductive (e.g. by soot, etc.) can also be used as the layer support.
  • the arrangement of the photoconductor layer can also be on a drum, on flexible endless belts, e.g. made of nickel or steel etc. or on plates.
  • All materials known for this purpose can be used as carrier materials for the electrophotographic production of printing forms, e.g. Aluminum, zinc, magnesium, copper plates or multi-metal plates. Surface-coated aluminum foils have proven particularly useful.
  • the surface refinement consists of mechanical or electrochemical roughening and, if appropriate, subsequent anodizing and treatment with polyvinylphosphonic acid in accordance with DE-OS 16 21 478, corresponding to US Pat. No. 4,153,461.
  • the aim of introducing an insulating intermediate layer is to reduce 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 also serves, if appropriate, to improve the adhesion between the layer support surface and the dye layer or photoconductor layer and should be able to be stripped off water or alcoholic-alkaline for the production of printing forms.
  • Different natural or synthetic resin binders can be used for the intermediate layer, but preference is given to using materials which adhere well to a metal, in particular aluminum surface, and which are poorly dissolved when subsequent layers are applied.
  • These include polyamide resins, polyvinyl alcohols, polyvinylphosphonic acid, polyurethanes, polyester resins or specifically alkali-soluble binders, such as, for example, styrene-maleic anhydride copolymers.
  • the thickness of organic intermediate layers can be up to 5 ⁇ m, that of an aluminum oxide intermediate layer is generally in the range from 0.01 to 1 J.lm.
  • the dye layer 2 or 5 according to the invention has the function of a layer which generates charge carriers; the dye used determines the spectral photosensitivity of the photoconductive system through its absorption behavior.
  • the application of a homogeneous, densely packed dye layer is preferably obtained by evaporating the dye onto the support in vacuo.
  • Can depending on the vacuum level, under the conditions of 1.33 x 10- 6 to 10- 8 bar and 240 to 270 ° 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 dye 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 dye are particularly favorable here.
  • a uniform dye 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 dye layers with thicknesses of the order of 0.05 to 3 ⁇ m can also be obtained by grinding the dye with binders, in particular with cellulose nitrates and / or crosslinking binder systems, for example polyisocyanate-crosslinkable acrylic resins, Reactive resins, such as epoxies, DD lacquers, and then coating these dye dispersions according to position 5 in FIGS. 4 and 5.
  • binders in particular with cellulose nitrates and / or crosslinking binder systems, for example polyisocyanate-crosslinkable acrylic resins, Reactive resins, such as epoxies, DD lacquers, and then coating these dye dispersions according to position 5 in FIGS. 4 and 5.
  • binders such as polystyrene, styrene-maleic anhydride copolymers, polymethacrylates, polyvinyl acetates, polyurethanes, polyvinyl butyrals, polycarbonates, polyesters etc. and mixtures thereof can be used.
  • the ratio of dye / binder can vary within wide limits, but preferred are dye primers with a dye content of over 50% and correspondingly high optical density.
  • Another possibility is to produce a photoconductor layer according to FIG. 1, in which the charge generation centers (dyes) are finely dispersed in the charge transport layer medium.
  • This arrangement has the advantage of a simpler production method than that of a double layer. It is particularly suitable for the production of lithographic printing forms.
  • the proportion of dye in the photoconductor layer is preferably up to about 30%.
  • the layer thickness of such arrangements is preferably 2 to 10 J.lm.
  • the inverse arrangement of the charge carrier-generating layer 5 in FIG. 5 on the charge-transporting layer 3 provides photoconductor double layers when using a p-transport connection have high photosensitivity when charged positively.
  • Organic materials which have an extensive x-electron system are particularly suitable as the material used for charge transport. These include both monomeric and polymeric aromatic or heterocyclic compounds.
  • the monomers used are in particular those which have at least one tertiary amino group and / or one 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; Further, unbalanced oxadiazoles, such as 5- [3- (9-ethyl) -carbazolyl] - 1,3,4-oxadiazole derivatives (U.S. Patent 4,192,677), such as 2- (4-dialkylaminophenyl -) - 5- [3 - (9-ethyl) -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- (o-chlorophenyl) -5 (p-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).
  • oxazole derivatives for example 2-phenyl-4- (o-chlorophenyl) -5 (p-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).
  • Formaldehyde condensation products with various aromatics such as, for example, condensates of formaldehyde and 3-bromopyrene, have proven to be suitable as polymers (DE-OS 21 37 288 corresponding to US Pat. No. 3,842,038).
  • polyvinyl carbazole or copolymers with at least 50% vinyl carbazole content as transport polymers provide good photosensitivity (FIGS. 2 to 4).
  • the charge transport 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 binder 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 1012 ⁇ . It prevents the discharge of electrostatic charge in the dark; when exposed, it transports the charges generated in the dye layer.
  • 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.
  • Polyester resins polyvinyl chloride / polyvinyl acetate copolymers, alkyd resins, polyvinyl acetates, polycarbonates, silicone resins, polyurethane, epoxy resins, poly (meth) acrylates and copolymers, polyvinyl acetals, polystyrenes and styrene copolymers, cellulose derivatives, such as cellulose acetate etc., are used as binders.
  • thermally post-crosslinking binder systems such as reactive resins, which are composed of an equivalent mixture of hydroxyl-containing polyesters or polyethers and polyfunctional isocyanates, polyisocyanate-crosslinkable acrylate resins, melamine resins, unsaturated polyester resins, etc., have been used successfully.
  • solubility properties play a particularly important role in the selection of binders.
  • binders which are soluble in aqueous or alcoholic solvent systems, optionally with the addition of acid or alkali are particularly suitable for practical purposes.
  • suitable binders are high-molecular substances which carry groups which render alkali soluble. Such groups are, for example, acid anhydride, carboxyl, phenol, sulfonic acid, sulfonamide or sulfonimide groups.
  • Copolymers with anhydride groups can be used with particularly good results.
  • Copolymers of ethylene or styrene and maleic anhydride or maleic acid semiesters are very particularly suitable.
  • Phenolic resins have also proven their worth.
  • Copolymers of styrene, methacrylic acid and methacrylic acid esters can also be used as alkali-soluble binders (DE-OS 27 55 851).
  • a copolymer of 1 to 35% styrene, 10 to 40% methacrylic acid and 35 to 83% methacrylic acid n-hexyl ester is used.
  • a terpolymer made from 10% styrene, 30% methacrylic acid and 60% methacrylic acid n-hexyl ester is extremely suitable.
  • Polyvinyl acetates (PVAc) in particular copolymers of PVAc and crotonic acid, can also be used.
  • the binders used can be used alone or in combination.
  • the mixing ratio of the charge transporting compound to the binder can vary. However, the requirement for maximum photosensitivity, i.e. as large a proportion of charge transport compound as possible, 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 about 1: 1 parts by weight has generally proven to be preferred, but ratios between 4 1 to 1: 4 are also suitable.
  • polymeric charge transport compounds such as bromopyrene resin, polyvinyl carbazole, binder proportions of around or below 30% are suitable.
  • the respective requirements of a copying machine for the electrophotographic and mechanical properties of the recording material can be met within a wide range by setting the layers differently, for example the viscosity of the binder, the proportion of the charge-transporting compound.
  • layer thicknesses between approximately 2 and 25 ⁇ m are generally used. A thickness range of 3 to 15 J.1m has proven to be particularly 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 individual cases.
  • Leveling agents such as silicone oils, wetting agents, in particular nonionic substances, plasticizers of different compositions, such as, for example, those based on phthalic acid esters, are considered to be conventional additives. If necessary, conventional sensitizers and / or acceptors can also be added to the charge-transporting layer, but only to the extent that their optical transparency is not significantly impaired.
  • An aluminum vapor-coated polyester film as the carrier material is gently vaporized at 1.33 x 10-7 - 10-8 bar with the dyes (formulas 1 to 4 of the attached dye table; the layer thicknesses of the homogeneous, yellow-orange colored dye layers are in the range of 125 - 150 mg / m 2 .
  • the test sample moves on a rotating plate through a charging device to the exposure station, where it is continuously exposed to an XBO 150 xenon lamp or, if applicable, a halogen-tungsten lamp (150 W).
  • a heat absorption glass and a neutral filter are installed upstream of the lamp.
  • the light intensity in the measurement plane is in the range from 30 to 50 ⁇ W / cm 2 or from 5 to 10 ⁇ W / cm 2 . It becomes immediately after or in parallel measured with an optometer to determine the light decay curve.
  • 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 (Uo) and the time (T 1/2 ) after which half the charge (U o / 2) is reached.
  • the product of T 112 (s) and the measured light intensity I ( ⁇ W / cm 2 ) is the half-value energy E 1/2 (pJ / cm 2 ).
  • the spectral photosensitivity of the double layers produced is determined with the use of filters using the method given in Example 1: In the case of negative charging (500-500 V), the half-life (T 1/2 in msec) for the respective wavelength range is determined by exposure. By plotting the reciprocal half-power 1 / E 1/2 (cm 2 / microjoules) ⁇ versus wavelength. (nm) the spectral photosensitivity curve is obtained. Dabie means the half-value energy E 1/2 ( ⁇ J / cm 2 ) that light energy that must be irradiated in order to discharge the layer to half the initial voltage U o .
  • curve 1 shows the spectral photosensitivity of the double layer a), which was determined with a charge of approximately -570 V and under xenon exposure.
  • a vapor deposition layer of dye according to formula 3 with a layer thickness of 285 mg / m 2 is coated with a solution of 65 parts To 1920 and 35 parts cellulose nitrate of standard type E 4 in tetrahydrofuran in a thickness of about 7 ⁇ m after drying.
  • the photosensitivity is determined as described in Example 1:
  • the spectral photosensitivity is determined with a negative charge of approx. 600 V using Xenon XBO lighting (FIG. 6, curve 2).
  • the mixing ratio of photoconductor compound and binder is 1: 1.
  • a vapor deposition layer according to Example 4 with a layer thickness of 50 mg / m 2 is coated with a solution of 90 parts of polyvinyl carbazole (Luvican R M170, BASF) and 10 parts of polyester resin (Adhesive 49,000 from du Pont) in tetrahydrofuran in a thickness of 4 to 5 1 1 m.
  • the photosensitivity E 1/2 is 3.06 ⁇ J / cm 2 at (-) 320 V.
  • the photosensitivity, measured according to Example 1, is:
  • the spectral photosensitivity of layer d) was measured in accordance with Example 2 in the negative charging range from 720 to 760 V (FIG. 7).
  • the measurement of the photosensitivity according to Example 1 gives positive and negative charging (400 V) half-value energies of 11.5 and 11.9 ⁇ J / cm 2 (tungsten halogen lamp 1-6.5 ⁇ W / cm 2 ).
  • a mixture of 2 parts of dye according to formula 3 and 1 part of cellulose nitrate of the standard type 4E (DIN 53 179) are ground together intensively in tetrahydrofuran for about 3 hours in a ball mill.
  • the finely dispersed solution is then homogeneously applied to an aluminum-vapor-coated polyester film in a thickness of approximately 150 mg / m 2 and dried.

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

Claims (5)

1. Matériau de reproduction électrophotographique composé d'un support de couche conducteur de l'électricité, éventuellement d'une couche intermédiaire isolante, et d'une couche photoconductrice constituée d'au moins une couche contenant un colorant en tant que composé producteur de porteurs de charges, un photoconducteur en tant de composé transporteur de charges, un liant et des additifs usuels, caractérisé en ce que dans la couche photoconductrice il contient en tant que colorant un dérivé benzo-benzimidazo[1,2-a]quinoléine.
2. Matériau de reproduction selon la revendication 1, caractérisé en ce que le colorant représente un composé de formule générale
Figure imgb0021
dans laquelle Ri représente un atome d'hydrogène ou un radical alkyle en C1-C4 qui peut être substitué par des atomes d'halogène et/ou par des groupes alcoxy en C1-C4, un radical cycloalkyle ou phényle éventuellement substitués,
R2 représente un atome d'hydrogène, le groupe hydroxy, un groupe alcoxy en C1-C4, le groupe cyano ou un groupe -COOR dans lequel R est H ou un radical alkyle en C1-C4;
R3 représente un groupe sulfophényle, cyano, acétyle, -COOR dans lequel R a la signification donnée ci-dessus, un groupe benzoxazolyle, benzimidazolyle ou benzothiazolyle;
R4 représente un atome d'hydrogène ou d'halogène; et
Rs représente un atome d'hydrogène, le groupe cyano ou un groupe -COOR dans lequel R est tel que défini ci-dessus.
3. Matériau de reproduction selon la revendication 2, caractérisé en ce que du chlore ou du brome est présente en tant qu'halogène.
4. Matériau de reproduction selon la revendication 1 ou 2, caractérisé en ce que le colorant est de formule
Figure imgb0022
5. Matériau de reproduction selon les revendications 1 à 4, caractérisé en ce que la couche photoconductrice est constituée d'une couche de colorant producteur de porteurs de charge et d'une couche de transport de charges.
EP86113419A 1985-10-08 1986-09-30 Matériau d'enregistrement électrophotographique Expired - Lifetime EP0218981B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853535838 DE3535838A1 (de) 1985-10-08 1985-10-08 Elektrophotographisches aufzeichnungsmaterial
DE3535838 1985-10-08

Publications (3)

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EP0218981A2 EP0218981A2 (fr) 1987-04-22
EP0218981A3 EP0218981A3 (en) 1987-06-16
EP0218981B1 true EP0218981B1 (fr) 1990-03-28

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EP86113419A Expired - Lifetime EP0218981B1 (fr) 1985-10-08 1986-09-30 Matériau d'enregistrement électrophotographique

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US (1) US4725520A (fr)
EP (1) EP0218981B1 (fr)
JP (1) JPS62125362A (fr)
DE (2) DE3535838A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5116709A (en) * 1989-06-13 1992-05-26 Industrial Technology Research Institute Electrophotoreceptor using styrene-maleic anhydride copolymer as the polymeric binder
US5139909A (en) * 1990-07-31 1992-08-18 Xerox Corporation Perinone photoconductive imaging members

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879200A (en) * 1970-12-01 1975-04-22 Xerox Corp Novel xerographic plate containing photoinjecting bis-benzimidazole pigments
FR2182125A1 (en) * 1972-04-26 1973-12-07 Kalle Ag Electrophotographic registration material - highly light sensitive, good abrasion resistance, etc
NL180460C (nl) * 1972-04-26 1987-02-16 Hoechst Ag Elektrofotografisch registratiemateriaal.
DE2353639C2 (de) * 1973-10-26 1983-08-04 Hoechst Ag, 6230 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
DE3110960A1 (de) * 1981-03-20 1982-09-30 Basf Ag, 6700 Ludwigshafen Elektrophotographisches aufzeichnungsmaterial
DE3339540A1 (de) * 1983-11-02 1985-05-09 Basf Ag, 6700 Ludwigshafen Elektrofotografisches aufzeichnungsmaterial
DE3502689A1 (de) * 1985-01-26 1986-07-31 Hoechst Ag, 6230 Frankfurt Elektrophotographisches aufzeichnungsmaterial
DE3502681A1 (de) * 1985-01-26 1986-07-31 Hoechst Ag, 6230 Frankfurt Elektrophotographisches aufzeichnungsmaterial

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Publication number Publication date
DE3535838A1 (de) 1987-04-09
EP0218981A2 (fr) 1987-04-22
US4725520A (en) 1988-02-16
DE3669934D1 (de) 1990-05-03
EP0218981A3 (en) 1987-06-16
JPS62125362A (ja) 1987-06-06

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