EP0210521A1 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0210521A1
EP0210521A1 EP86109609A EP86109609A EP0210521A1 EP 0210521 A1 EP0210521 A1 EP 0210521A1 EP 86109609 A EP86109609 A EP 86109609A EP 86109609 A EP86109609 A EP 86109609A EP 0210521 A1 EP0210521 A1 EP 0210521A1
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Prior art keywords
layer
recording material
alkyl
perylene
tetracarboximide
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EP86109609A
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German (de)
English (en)
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EP0210521B1 (fr
Inventor
Wolfgang Dr. Wiedemann
Ernst Dr. Spietschka
Helmut Dr. Tröster
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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
    • G03G5/0659—Heterocyclic compounds containing two or more hetero rings in the same ring system containing more than seven 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, 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
    • G03G5/0657—Heterocyclic compounds containing two or more hetero rings in the same ring system containing seven 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 compound which produces a perylene-3,4,9,10-tetracarboximide derivative as charge carrier, photoconductor as charge transport compound, binder and conventional additives .
  • the invention relates in particular to a recording material comprising an electrically conductive layer support, optionally an insulating intermediate layer, a dye layer with a perylene-3,4,9,10-tetracarboximide derivative as the charge-generating compound and an organic photoconductor as the charge transport compound layer.
  • 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 perylene-3,4,9,10-tetracarboxylic acid derivatives have, as red colored dyes, photosensitivities which range approximately in the range from 620 to 650 nm. It was an object of the invention to find new perylene-3,4,9,10-tetracarboxylic acid derivatives which, if possible, also have good photosensitivity up to 700 nm.
  • an electrophotographic recording material of the type mentioned at the outset in that it contains an asymmetrically substituted perylene-3,4,9,10-tetracarboxylic acid imide in the photoconductive layer.
  • the perylene carboximide according to the invention has one of the following structures: in the R -hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, aryl or aralkyl and A -phenylene, naphthylene or a more condensed aromatic carbocyclic or heterocyclic radical, each of which can be substituted by halogen, alkyl, the cyano or nitro group, in which R and R 'are not the same and are hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aryl, aralkyl or heteroaryl, which can each be substituted by halogen, alkyl, the cyano or nitro group, or in the R -hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, aryl, aralkyl or heteroaryl, each of which can be substituted by halogen, alkyl, the cyano or nitro group.
  • carbocyclic or heterocyclic radicals examples include naphthylene-1,8 or pyridyl radicals. Cyclohexyl, for example, is suitable as the cycloalkyl.
  • the asymmetrical perylene-3,4,9,10-tetracarboximides according to the invention as charge-producing pigments with many organic pho toleitern, the charge transport compounds, and especially with binders good photosensitive recording materials, both in double and in monolayer arrangement with pigment dispersed therein.
  • the asymmetrical pigments according to the invention have high photosensitivity down to a range of almost 700 nm. This also permits their use in electrophotographic recording materials for He / Ne and LED laser light sources.
  • the substituent R can preferably be hydrogen, alkyl, such as methyl to butyl, hydroxyalkyl, such as 2-hydroxyethyl, alkoxyalkyl, such as 3-methoxypropyl and aralkyl, such as benzyl.
  • the derivatives of the perylene-3,4,9,10-tetracarboxylic acid monoanhydride monoimide (b) can also be used successfully as charge-generating compounds. Because of their good alkali solubility, they can preferably be used in alkali-strippable lithographic printing forms.
  • Position 1 indicates the electrically conductive layer support
  • position 2 indicates the charge layer producing dye layer
  • position 3 indicates the charge transport layer
  • Position 4 indicates the insulating intermediate layer
  • position 5 shows layers which represent a charge carrier-producing dye layer in dispersion.
  • Position 6 shows a photoconductive monolayer of photoconductor, peryien-3,4,9,10-tetracarboximide 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 capable of being stripped off water or alcoholic-alkaline for the production of printing forms.
  • 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, polyvinyl phosphonic 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 u, that of an aluminum oxide intermediate layer is generally in the range from 0.01 to 1 u.m.
  • 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 pigment onto the support in vacuo.
  • the dye can be evaporated without decomposition under the conditions of 1.33 x 10 -1 to 10 -2 bar and a heating temperature of 240 to 290 ° C.
  • 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 pigment 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 dye 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 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 then coating these dye dispersions according to position 5 in FIGS. 4 and 5.
  • 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 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 preference is given to pigment primers with a pigment content of over 50% and correspondingly high optical density.
  • FIG. 1 Another possibility is to produce a photoconductor layer according to FIG. 1, in which the charge generation centers (pigments) are finely dispersed in the transport layer medium.
  • This arrangement has the advantage of a simpler production method than that of a double layer, and is particularly suitable for the production of lithographic printing forms.
  • the pigment content in the photoconductor layer is preferably up to about 30%.
  • the layer thickness of such arrangements is preferably 2 to 10 ⁇ m.
  • the inverse arrangement of the charge carrier-generating layer 5 in FIG. 5 on the charge-transporting layer 3, when using a p-transport connection, provides photoconductor double layers which have a high photosensitivity when charged positively.
  • 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 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; unsymmetrical oxdiazoles, such as 5- [3- (9-ethyl) -carbazolyl] -1,3,4-oxdiazole derivatives (US Pat. No. 4,192,677), about 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-triphenytpyrazoiine 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 US-PS 3,112,197, GB-PS 1,016,520, US-PS 3,257,203).
  • 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 US-PS 3,112,197, GB-PS 1,016,520, US-PS 3,257,203).
  • Hydrazone derivatives of the following structures have also become a charge transport compound according to US-PS 4,150,987, DE-OS 29 41 509, DE-OS 29 19 791, DE-OS 29 39 483 (corresponding to US-PS 4,338,388, US-PS 4,278,747, GB-PS 2,034,493) proven.
  • 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-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 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 10 12 12. It prevents the discharge of the 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, polyurethanes, 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, potashisocyanate-crosslinkable acrylate resins, melamine resins, unsaturated polyester resins etc. are successfully used.
  • 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 then high molecular weight substances which carry alkali-solubilizing groups.
  • alkali-solubilizing 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 of 10% styrofoam, 30% methacrylic acid and 60% methacrylic acid n-hexyl ester is particularly 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, due to the requirement for maximum photosensitivity, ie the largest possible proportion of charge transport compound and for crystallization to be avoided as well Increasing flexibility, ie the greatest possible proportion of binders, sets 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.
  • polymeric charge transport compounds such as bromopyrene resin, polyvinyl carbazole, binder proportions of around or below 30% are suitable.
  • layer thicknesses between approximately 2 and 25 ⁇ m are generally used. A thickness range from 3 to 15 ⁇ m 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 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. 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.
  • the layer support is completely covered.
  • the residual charge (U R ) after 0.1 sec., Determined from the above bright discharge curves, is a further measure of the discharge of a photoconductor layer.
  • the pigment layers with the asymmetrical perylimide dyes according to formula I, 1 and 2, are produced as described in Example 1. These vapor deposition layers are then coated with a solution of 65 parts by weight To 1920 and 35 parts by weight cellulose nitrate of the standard type 4E (DIN 53179) in THF. After drying, the layer thicknesses ranged from 7 to 8 and 12 to 13 ⁇ m.
  • the spectral photosensitivity of these photoconductor double layers is determined with filters connected upstream according to the method given in Example 1: In the case of negative charging (500 to 550 V), the half-life - (T 1/2 in msec) for the respective wavelength range is determined by exposure.
  • the spectral photosensitivity curve of a photoconductor layer is obtained by plotting the reciprocal half-value energy (1 / E 1/2 cm 2 / ⁇ J) against the wavelength ⁇ (nm).
  • the half-value energy E 1/2 / mJ / cm 2 means the light energy that has to be irradiated in order to discharge the photoconductor layer to half the initial voltage U o .
  • a pigment evaporation layer with pigment according to formula I, 1 is coated with a solution of equal parts by weight of 2-phenyl-4- (2'-chlorophenyl) -5 (4'-diethylaminophenyl) oxazole (Table: Layer 3 - 1) and a polyester resin ( Dynapol R L206) coated in THF.
  • 2- (4'-diethylaminophenyl) 4-chloro-5 (4'-methoxyphenyl) oxazole was used instead of this oxazole derivative (Table: Layer 3 - 2).
  • the two double layers with a layer thickness of 7 to 8 ⁇ gave the following photosensitivity:
  • a mixture of 65 parts by weight of pigment (formula 1, 2), 25 parts by weight of cellulose nitrate of standard type 4E (DIN 53179) and 10 parts by weight of epoxy resin (Epikote R 1001) are ground together intensively in THF for 2 to 3 hours in a ball mill.
  • the finely dispersed solution is then homogeneously applied to a conductive support in thicknesses of approximately 210 mg / m 2 and approximately 490 mg / m 2 and dried.
  • part of the pigment precoat was polished with cotton wool.
  • the pigment pre-coat (approx. 490 mg / m '), which is insoluble for the subsequent coating of the charge transport layer, is mixed with a solution of equal parts by weight To 1920 and a copolymer of styrene / butadiene (Pliolite R S5B) and coated with a solution of 98 parts by weight of polyvinyl carbazole (Luvican R M170, BASF) and 2 parts by weight of polyester resin (Adhesive R 49000) in THF. After drying, the double layer is 4 to 5 ⁇ m thick; their photosensitivity is determined according to Example 1:
  • An aluminum-vapor-coated polyester film is vacuum-coated with the pigments according to formula II, 1 and 2 in a thickness of approximately 200 mg / m 2 .
  • the homogeneous pigment layers are then coated with a solution of equal parts by weight of 2- (4-diethylaminophenyl) -4-chloro-5- (4-methoxyphenyl) oxazole and polycarbonate (Makrolon R 2405) in a thickness of about 8 ⁇ m after drying.
  • the photosensitivity is measured analogously to Example 1:
  • pigment according to formula I, 2 5 parts are added to a solution of 45 parts of To 1920 and 50 parts of copolymer of syrene and maleic anhydride (Scipset R 550). This dispersion is ground very finely in a ball mill for about 2 hours and then layered on wire-brushed aluminum foil (a) and anodized aluminum foil (b) in a thickness of 7 to 8 ⁇ m.
  • the dye After the dye has been prepared in accordance with formula III, 1 (DE-OS 30 17 .185), it is aluminum-vaporized in a vacuum vapor deposition system at 1.3 ⁇ 10 -7 to 10 -4 bar within 7 minutes at about 250 ° C. Evaporated polyester film. A homogeneous, red vapor deposition layer with a layer weight of 135 mg / m 2 is obtained.
  • a solution of 65 parts by weight of To 1920 and 35 parts by weight of cellulose nitrate of standard type 4E is thrown into THF. After drying, the thickness of the charge transport layer is approximately 10 ⁇ m.
  • Dye vapor deposition layers in a thickness range of 135 to 140 mg / m 2 are produced with the compounds III, 1 and II, 6, as described in Example 11. This is followed by a charge transport layer consisting of equal parts by weight To 1920 and a copolymer of styrene and maleic anhydride (Scipset R 550). The total layer thickness is approximately 10 ⁇ m.
  • the photosensitivity is measured analogously to Example 1:
  • a solution of 45 parts of To 1920 and 50 parts of copolymer of styrene and maleic anhydride (Scripset R 550) is mixed with 5 parts of dye according to formula III, 6 and very finely dispersed in a ball mill for about 2 hours. This dispersion is then layered on wire-brushed aluminum foil in a thickness of approx. 10 ⁇ m.
  • the photosensitivity with positive (+) and negative (-) charging gives the following values (halogen-tungsten lamp).
  • Evaporation layers with the perylenetetracarboxylic acid monoimides III, 2 and 3 are produced in 115 and 110 mg / m 2 thickness, as described in Example 1.
  • a solution of 66.7 parts To 1920 and 33.3 parts cellulose nitrate of standard type 4E (DIN 53179) in THF is layered on top. After drying, the layer thickness was 10 to 11 ⁇ m.
  • the homogeneous, strongly red colored dye layers are coated with a solution of 50 parts To 1920, 25 parts polyester resin (Dynapol R L206) and 25 parts polyvinyl chloride-polyvinyl acetate copolymer (Hostaflex R M131) in a thickness of 8 to 9 ⁇ m.
  • the photosensitivity according to Example 1, measured under halogen tungsten light, is:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP86109609A 1985-07-23 1986-07-14 Matériau d'enregistrement électrophotographique Expired - Lifetime EP0210521B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3526249 1985-07-23
DE19853526249 DE3526249A1 (de) 1985-07-23 1985-07-23 Elektrophotographisches aufzeichnungsmaterial

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EP0210521A1 true EP0210521A1 (fr) 1987-02-04
EP0210521B1 EP0210521B1 (fr) 1990-05-23

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US (1) US4714666A (fr)
EP (1) EP0210521B1 (fr)
JP (1) JPS6254267A (fr)
DE (2) DE3526249A1 (fr)

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EP0409160A2 (fr) * 1989-07-21 1991-01-23 Eastman Kodak Company Eléments d'enregistrement électrophotographique contenant une combinaison de matériaux perylène photoconducteurs
EP0409160A3 (en) * 1989-07-21 1991-05-29 Eastman Kodak Company Electrophotographic recording elements containing a combination of photoconductive perylene materials
EP0447826A1 (fr) * 1990-02-23 1991-09-25 Eastman Kodak Company Eléments d'enregistrement électrophotographiques contenant des pigments de pérylène photoconducteurs
EP0695972A1 (fr) * 1994-07-20 1996-02-07 Konica Corporation Photorécepteur électrophotographique
US5589309A (en) * 1994-07-20 1996-12-31 Konica Corporation Electrophotographic photoreceptor containing perylenes

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DE3671549D1 (de) 1990-06-28
JPS6254267A (ja) 1987-03-09
EP0210521B1 (fr) 1990-05-23
DE3526249A1 (de) 1987-01-29
US4714666A (en) 1987-12-22

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