EP0001599B1 - Matériau électrophotographique et son application dans des procédés d'enregistrement - Google Patents

Matériau électrophotographique et son application dans des procédés d'enregistrement Download PDF

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Publication number
EP0001599B1
EP0001599B1 EP78101087A EP78101087A EP0001599B1 EP 0001599 B1 EP0001599 B1 EP 0001599B1 EP 78101087 A EP78101087 A EP 78101087A EP 78101087 A EP78101087 A EP 78101087A EP 0001599 B1 EP0001599 B1 EP 0001599B1
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EP
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Prior art keywords
recording material
electrophotographic recording
transport layer
diphenylhydrazone
charge
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EP78101087A
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German (de)
English (en)
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EP0001599A1 (fr
Inventor
Howard Warren Anderson
Michael Thomas Moore
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International Business Machines Corp
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International Business Machines Corp
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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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0616—Hydrazines; Hydrazones
    • 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
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • 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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0638—Heterocyclic compounds containing one hetero ring being six-membered containing two hetero atoms
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group

Definitions

  • the invention relates to an electrophotographic recording material comprising an electrically conductive layer support, a charge generation layer and a binder-containing charge transport layer and its use in a copying process.
  • Electrophotographic processes and materials are known. In these processes, a uniform electrostatic charge is applied to a normally insulating plate or element under so-called “dark" conditions. The element is then exposed imagewise, the areas of the element struck by the light becoming conductive and allowing the electrostatic charge to be dissipated from the surface of the element. This creates a latent image in the form of charged surface areas in the parts of the surface that have not been struck by light.
  • the electrostatic image on the surface of the element is then developed with an oppositely charged powder developer, a toner. This is held onto the charged areas of the element by its affinity for the opposite charge. The discharged areas of the element show no affinity of this kind for the toner.
  • the toner image thus formed is then transferred to another surface, for example on paper, and is fixed thereon by means of additives which are sensitive to pressure or heat or are admixed with the toner.
  • a particularly advantageous electrophotographic element is obtained when a layer which generates charge carriers and is sensitive to actinic radiation for forming electron-hole pairs is used in conjunction with a p-type charge carrier transport layer adjacent to it.
  • Numerous layers which generate charge carriers and are sensitive to certain wavelengths of actinic radiation are known.
  • the carrier transport layer is not sensitive to actinic radiation under the conditions used, but it serves to transfer positive charges from the carrier generation layer either to the surface of the negatively charged carrier transport layer on which the image is formed, or depending on the system used to be transported to the conductive base in a system with a positive charge.
  • US Pat. No. 3,837,851 describes an electrophotographic plate in which a tri-aryl-pyrazoline compound is used as the active material in the charge carrier transport layer.
  • Hydrazones have already been used as a radiation-sensitive material in photoconductive layers.
  • U.S. Patent 3,717,462 describes the corresponding use of a hydrazone compound. Similar uses of hydrazone compounds can be found, for example, in US Pat. No. 3,765,884.
  • an electrophotographic recording material comprising an electrically conductive layer support, a charge carrier-generating layer and a binder-containing charge carrier transport layer, which contains a charge carrier transport layer containing a hydrazone compound, as characterized in the claims.
  • p-diethylaminobenzaldehyde diphenylhydrazone
  • Other preferred charge carrier transport materials are o-ethoxy-p-diethylaminobenzaldehyde (diphenylhydrazone), o-methyl-p-diethylaminobenzaldehyde (diphenylhydrazone), o-methyl-p-dimethylaminobenzaldehyde (diphenylhydrazone), p-dipropylaminobenzaldehyde (diphenyl) p-diethylaminobenzaldehyde (benzylphenylhydrazone), p-dibutylaminobenzaldehyde (diphenylhydrazone) and p-dimethylaminobenzaldehyde (diphenylhydrazone).
  • Multi-layer electrophotographic recording materials are generally known.
  • the charge-generating layer which can consist of an organic or inorganic material, is resistant to actinic radiation that strikes the material to form Electron-hole pairs sensitive.
  • the charge carrier generating layer can be self-supporting, but a flexible base, such as a polymer film with a metallized surface, is preferably used. Biaxially oriented polyethylene terephthalate is preferably used as the flexible base.
  • the carrier generation layer must be in electrical contact with a conductor in order to facilitate the selective discharge of the recording material.
  • the charge carrier generating layer is preferably formed on the base and in contact with the conductive layer.
  • the layer thickness of the layer generating charge carriers is not critical, but is generally between 0.05 and 0.20 ⁇ m.
  • Materials generating inorganic charge carriers include selenium, tellurium and compounds of groups II b and VI a of the periodic system, for example cadmium sulfoselenide.
  • Materials which generate organic charge carriers include cyanine compounds, which are described, for example, in German Offenlegungsschrift 22 15 040, disazo compounds, which are described, for example, in German Offenlegungsschriften 2215968 and 26 35 887, or phthalocyanine compounds. Useful results are also obtained with charge generating materials that include methine dye derivatives of squaric acid. Materials of this type are discussed in German Offenlegungsschrift 2401 220.
  • Chlorodian blue, methylsquarylium and hydroxysquarylium dyes are particularly suitable charge-generating materials.
  • preferred materials of this type are 3,3'-dichloro-4,4'-diphenyl-bis [1 "-azo-2" -hydroxy-3 "-naphtanilide] 2,4-bis (2-methyl-4-dimethylaminophenyl) cyclobutenediylium-1,3-diolate 2,4-bis (2-hydroxy-4-dimethylaminophenyl) cyclobutenediylium 1,3-diolate
  • these dyes are referred to below as chlorodian blue, methylsquarylium and hydroxysquarylium.
  • the charge carrier transport material in most embodiments of the invention must be substantially transparent to the actinic radiation which activates the charge carrier generating material, it is preferred that the charge carrier generating material is sensitive to actinic radiation in the visible and longer-wave spectral range, i.e. sensitive to light with a wavelength greater than 390 nm. This requirement is essential for the preferred exemplary embodiment of the invention, in which the charge carrier transport layer is arranged between the charge carrier generating layer and the radiation source, which is the case with a system with negative charging.
  • the carrier generation material is directly exposed to actinic radiation and the carrier transport material is disposed between the carrier generation material and the conductive carrier.
  • charge generating materials and radiation sources that operate at shorter wavelengths than visible light are suitable for use with the charge transport material of the present invention.
  • organic charge generating materials are used, these materials are applied in a known manner to a metallized base, for example by meniscus coating, by means of a doctor blade or in a dip coating process.
  • An adhesive layer is preferably applied to the base in order to improve the adhesion of the charge carrier-generating layer thereon. Polyester resins are preferred as adhesives.
  • the charge carrier transport layer according to the invention is preferably applied to the charge carrier generating layer and forms the uppermost or exposed layer of the recording material.
  • the charge carrier transport layer has a thickness between about 7 and 35 ⁇ m, but can also be thicker or thinner, for example less than 7 ⁇ m, i.e. 5 ⁇ m.
  • the charge carrier transport layer can also be arranged between the charge carrier generating layer and the base, as indicated in two figures and the associated explanations.
  • the active material of the p-type charge transport layer according to the present invention is a hydrazone of the general formula in which the leftovers mean.
  • a particularly preferred charge carrier transport material is p-diethylaminobenzaldehyde (diphenylhydrazone);
  • charge carrier transport materials are o-ethoxy-p-diethylamino-benzaldehyde (diphenylhydrazone) o-methyl-p-diethylaminobenzaldehyde- (diphenylhydrazone) o-methyl p-dimethylaminobenzaldehyde- (diphenylhydrazone) p-dipropylaminobenzaldehyde (diphenylhydrazone) p-diethylaminobenzaldehyde (benzylphenylhydrazone) p-dibutylaminobenzaldehyde (diphenylhydrazone) p-dimethylaminobenzaldehyde (diphenylhydrazone)
  • the hydrazone material is mixed with a binder in an organic solvent, applied to the charge-generating layer and dried in a forced air oven.
  • binders are polycarbonate resins, for example a resin which is available under the name M-60 from Mobay Chemical Company, polyester resins, for example a resin which is available under the name PE-200 from Goodyear and Acrylic resins, for example a resin available under the designation A-1 from Rohm and Haas.
  • Various other resins are also suitable, as shown below.
  • the resins, which can be used individually or in mixtures, are mixed with one or more organic solvents, preferably with tetrahydrofuran and toluene, although other suitable solvents can also be used.
  • a silicone oil available under the trademark DC-200 from Dow Corning, is incorporated into the solution of the charge carrier transport material.
  • a multilayer electrophotographic recording material in Fig. 1 is generally designated by the reference numeral 10.
  • the recording material 10 comprises a charge generation layer 12 and a charge transport layer 14. As shown, there is a negative charge on the surface of the charge transport layer 14. A positive charge is on the opposite side of the charge generation layer 12, i.e. in a conductive layer, which is not shown. Actinic radiation 16 passes through the charge carrier transport layer 14 in the region 18, penetrates into the charge carrier generating layer 12 and generates electron-hole pairs. The hole is attracted to the negative charge on the surface of the carrier transport layer 14 and, as shown in Fig. 2, is injected into the carrier transport layer and migrates through the layer 14 to discharge the region 18.
  • the carrier transport layer 14 is essentially in view of that negative charge on it made of an insulating material. In this way, a localized discharge is obtained in the area 18. The electron is attracted to the positive charge in the conductive pad (not shown).
  • FIGS. 3 and 4 A similar result is shown in FIGS. 3 and 4.
  • the charge carrier-generating layer 12 is charged positively and irradiated directly with actinic radiation 16.
  • the charge carrier transport layer 14 is arranged between the charge carrier generating layer 12 and a negative charge, which is located in the conductive base, not shown.
  • Actinic radiation in turn creates 16 electron-hole pairs.
  • the area 18 of the charge carrier generating layer 12 is discharged by electrons, while the corresponding holes migrate through the charge carrier transport layer 14 and are attracted to the negative charges.
  • the recording material 10 ' has the advantage that actinic radiation 16 does not have to penetrate the charge carrier transport layer 14, on the other hand the charge carrier generating layer 12 is not protected.
  • Other exemplary embodiments are also possible, which are not shown.
  • the recording material 10 in Fig. 1 can also be viewed from the opposite side, e.g. through the support, exposed to actinic radiation.
  • a backing suitable for the present invention was prepared by coating an aluminized polyethylene terephthalate support with a solution of a polyester resin which was mixed in a tetrahydrofuran: toluene solvent mixture in a ratio of 9: 1 (0.7% to 1.4% solids content, weight : Weight) was solved.
  • the polyester coating was applied using a meniscus coating process and dried in a forced air oven.
  • chlorodian blue (0.73 g% solids content) was dissolved in a mixture of ethylene diamine, n-butylamine and tetrahydrofuran in a weight ratio of 1.2: 1.0: 2.2. Silicone oil was then added in an amount of 2.3% by weight based on the chlorordian blue.
  • the resulting solution was applied to the polyester-coated support by a meniscus coating method and the resulting coated base was dried in a forced air oven.
  • the production of the layer producing chlorine dian blue on a conventional polyester base is known per se.
  • the new charge carrier transport layer according to the invention was prepared by mixing a polycarbonate resin binder in an amount of 7.65 g, a polyester resin in an amount of 3.60 g and an acrylic resin in an amount of 2.25 g in 86.5 tetrahydrofuran and Toluene, the solvents being in a weight ratio of about 9: 1.
  • a polycarbonate resin binder in an amount of 7.65 g
  • a polyester resin in an amount of 3.60 g
  • an acrylic resin in an amount of 2.25 g in 86.5 tetrahydrofuran and Toluene
  • the solvents being in a weight ratio of about 9: 1.
  • p-diethylaminobenzaldehyde (diphenylhydrazone) is added in an amount of 9.0 g together with 0.02 g of silicone oil.
  • Further tetrahydrofuran can be added to adjust the viscosity, which is suitable for the chosen coating method.
  • the resulting solution was applied to the previously produced carrier generation layer and the entire film was again dried in a forced air oven to obtain a multilayer electrophotographic recording material.
  • the electrophotographic recording material was tested by charging the surface to -870 volts in the dark, exposing the charged electrophotographic recording material to light used in commercial electrophotographic equipment under various conditions of light intensity and by the light intensity required to achieve this Discharge of recording material to a voltage of - 150 volts within 454 ms under the specified conditions was determined. It was found that 1.10 pt / cm 2 was required to discharge the recording material of the present example. This value indicates excellent hole transport. Electrophotographic recording materials identical to those of the present examples were tested in commercial copying machines and gave excellent results in terms of charge transport, resistance to toner film formation, physical resistance to wear, long-term stability of electrical and physical properties and working at low temperature.
  • Multilayer electrophotographic recording materials similar to that made in Example 1 were made with different resins in different amounts in the charge transport layer.
  • a multilayer electrophotographic recording material similar to that in Example 1 was prepared except that the solution for preparing the charge carrier transport layer contained 14.5 g of acrylic resin as the sole binder and 14.5 g of p-diethylamino-benzaldehyde (diphenylhydrazone).
  • the recording material was tested as in Example 1, it was found that 3.0 ⁇ / cm2 of light energy was required to discharge the recording material from a voltage in the dark from -870 V to 150 V with a response time to exposure of 454 ms.
  • a multilayer electrophotographic recording material similar to that prepared in Example 1 was made except that a different acrylic resin was used. When tested as in Example 1, it was found that 1.16 ⁇ / cm 2 of light energy was required to discharge the recording material from a voltage in the dark from -870 V to -150 V with a response time to exposure of 454 ms ' .
  • Multilayer electrophotographic recording materials similar to that of Example 2 were prepared except that the following polyester resins were used in place of the polyester resin specified therein. Results similar to those of Example 2e were obtained in each case.
  • Multilayer electrophotographic recording materials similar to that in Example 1 were made, except that the adhesive layers applied first were made with resins other than the polyester specified there, but in similar amounts.
  • Each recording material was charged to -870 V and discharged to -150 V in 146 ms.
  • the exposure energies given below in ⁇ / cm 2 were required.
  • Multilayer electrophotographic recordings similar to that prepared in Example 2e were made except that 5.78 g of p-diethylamino-benzaldehyde (diphenylhydrazone) was used in the charge carrier sport layer solution in Example 7a and 7.27 g in Example 7b were.
  • p-diethylamino-benzaldehyde diphenylhydrazone
  • a multilayer electrophotographic recording medium similar to that of Example 2a was prepared except that 13.5 g of p-diethylaminobenzaldehyde (diphenylhydrazone) was used in the solution of the charge transport layer.
  • p-diethylaminobenzaldehyde diphenylhydrazone
  • 1.37 ⁇ / cm 2 of light energy was required to discharge the recording material from a dark voltage of -870 V to -150 V with a response time to exposure of 146 ms.
  • a multilayer electrophotographic recording medium similar to that in Example 2a was prepared except that 20.25 g of p-diethylaminobenzaldehyde (diphenylhydrazone) was used in the solution of the charge transport layer.
  • p-diethylaminobenzaldehyde diphenylhydrazone
  • Multilayer electrophotographic recordings similar to that in Example 1 were made except that the charge transport layer solution contained 6.75 g polyester resin, 6.75 g polycarbonate resin and 13.5 g of the hydrazone compounds shown below:
  • hydroxysquarylium in an amount of 1 g is dissolved in a mixed solvent of 1 ml of ethylenediamine, 5 ml of propylamine and 24 ml of tetrahydrofuran and applied to an aluminized polyester base by a meniscus coating method and dried to obtain a layer generating charge carriers.
  • a charge carrier transport layer according to the present invention was produced by meniscus coating the support-coated layer with a solution of 8.12 g of a polycarbonate resin and 8.12 g of p-diethylaminobenzaldehyde (diphenylhydrazone) in a 9: 1 mixture of tetrahydrofuran and toluene and drying to form a multilayer electrophotographic recording material.
  • a solution of 8.12 g of a polycarbonate resin and 8.12 g of p-diethylaminobenzaldehyde (diphenylhydrazone) in a 9: 1 mixture of tetrahydrofuran and toluene and drying to form a multilayer electrophotographic recording material.
  • 1.40 ⁇ / cm 2 of light energy was required to discharge the recording material from a voltage in the dark from -870 V to -150 V with a response time to exposure of 146 ms.
  • a multilayer electrophotographic recording material similar to that in Example 13 was made except that o-ethoxy-p-diethylaminobenzaldehyde (diphenylhydrazone) was used in the charge transport layer solution.
  • o-ethoxy-p-diethylaminobenzaldehyde diphenylhydrazone
  • a multilayer electrophotographic recording material similar to that in Example 13 was prepared except that the carrier generation layer solution contained 0.85 g of hydroxysquarylium and 0.15 g of methylsquarylium. When tested as in Example 1, it was found that 0.86 ⁇ / cm 2 of light energy was required to discharge the recording material from a voltage in the dark from -870 V to -150 V with a response time to exposure of 146 ms.
  • a multilayer electrophotographic recording material similar to that in Example 13 was prepared except that the solution of the carrier generation layer was 0.85 g of hydroxysquarylium and 0.15 g of methylsquarylium and the solution of the carrier transport layer was 8.12 g of polycarbonate resin and 5 , 42 g of p-diethylaminobenzaldehyde (diphenylhydrazone) contained.
  • the solution of the carrier generation layer was 0.85 g of hydroxysquarylium and 0.15 g of methylsquarylium and the solution of the carrier transport layer was 8.12 g of polycarbonate resin and 5 , 42 g of p-diethylaminobenzaldehyde (diphenylhydrazone) contained.
  • the solution of the carrier generation layer was 0.85 g of hydroxysquarylium and 0.15 g of methylsquarylium
  • the solution of the carrier transport layer was 8.12 g of polycarbonate resin and 5 , 42 g of p-diethylamin
  • a multilayer electrophotographic recording material was prepared by adding a charge transport layer composed of a solution of 6.75 g polyester resin, 6.75 g polycarbonate resin and 13.5 g p-diethylaminobenzaldehyde to a charge-generating layer which had been produced by vacuum deposition of selenium and tellurium - (Diphenylhydrazone) was applied.
  • a charge transport layer composed of a solution of 6.75 g polyester resin, 6.75 g polycarbonate resin and 13.5 g p-diethylaminobenzaldehyde
  • the p-type charge transport layer according to the present invention can be made with various types of resin binders as well as a variety of hydrazone compounds of the specified type.
  • Both organic and inorganic charge generation layers can be used with the charge transport layer according to the present invention, and various combinations of solvents, polymeric binders and the like known per se can be used.
  • Certain hydrazone compounds show when in relatively high concentrations a tendency to crystallize, thereby decreasing their charge transport function. However, if smaller amounts are used, useful results will be obtained. A selection in this direction can be made by a person skilled in the art.
  • the electrophotographic recording materials with the charge carrier transport layer according to the invention show an excellent ratio of sensitivity, in particular at low temperatures, adhesion to adjacent layers and resistance to mechanical wear, again at different temperatures.
  • the recording materials also show in terms of. Aging excellent properties and have considerable resistance to toner film formation.

Claims (12)

1. Matériau d'enregistrement électrophotographique composé d'un support de couche électriquement conducteur, d'une couche générant des porteurs de charge, et d'une couche de transport de porteurs de charge contenant un liant, caractérisé en ce que la couche de transport de porteurs de charge contient comme composé transportant des charges une hydrazone de formule générale:
Figure imgb0025
avec les résidus
Figure imgb0026
2. Matériau d'enregistrement électrophotographique selon la revendication 1, caractérise en ce que la couche de transport de porteurs de charge contient une hydrazone choisie dans le groupe comprenant; p-diethylaminobenzaldehyde (diphenylhydrazone), o-ethoxy-p-diethylaminobenzaldehyde-(diphenylhydrazone), o-methyl-p-diethylaminobenzaldehyde-(diphenylhydrazone), o-methyl-p-di- methylaminobenzafdehyde-(diphenylhydrazone), p-dipropylaminobenzaldehyde-(diphenylhydrazone), p-diethylaminobenzaldehyde-(benzylphenylhydrazone), p-dibutylaminobenzaldehyde-(diphenylhydrazone), p-dimethylaminobenzaldehyde-(diphenylhydrazone).
3. Matériau d'enregistrement électrophotographique selon la revendication 1, caractérisé en ce que la couche de transport de porteurs de charge contient comme liant polymère une résine polycarbonate, und résine polyester, ou un résine acrylique, ou un mélange de celles-ci.
4. Matériau d'enregistrement électrophotographique selon les revendications 1, 2 et 3, caractérisé en ce que la couche de transport de porteurs de charge contient de la p-diethylaminobenzaldehyde-(diphenylhydrazone), et une résine polycarbonate, une résine polyester, ou une résine acrylique, ou des mélanges de celles-ci.
5. Matériau d'enregistrement électrophotographique selon les revendications 1 et 4, caractérisé en ce que la couche de transport de porteurs de charge a une épaisseur comprise entre 7 et 35 ,um.
6. Matériau d'enregistrement électrophotographique selon les revendications 1 à 5, caractérisé en ce que la couche de transport de porteurs de charge est du type p.
7. Matériau d'enregistrement électrophotographique selon la revendication 1, caractérisé en ce que la couche de transport de porteurs de charge est disposée sur la couche générant les porteurs de charge.
8. Matériau d'enregistrement éiectrophotographique selon la revendication 1, caractérisé en ce que la couche générant les porteurs de charge comporte un photoconducteur choisi dans le groupe comprenant le sélénium, le tellure ou des alliages de ceux-ci; des composés d'éléments du groupe Ilb avec ceux du groupe Via de la classification périodique; les cyanines, les diazoïques, les phthalocyanines, et les colorants de méthine dérivés de l'acide squarique.
9. Matériau d'enregistrement électrophotographique selon la revendication 8, caractérisé en ce que la couche générant les porteurs de charge contient du bleu chlorodiane, du méthyl squarylium et/ou de l'hydroxy squarylium.
10. Matériau d'enregistrement électrophotographique selon l'une ou plusieurs des revendications 1 à 9, caractérisé en ce que le couche générant les porteurs de charge a une épaisseur comprise entre 0,05 et 0,2 µm et que la couche de transport de porteurs de charge a une épaisseur d'au moins 5 um.
11. Matériau d'enregistrement électrophotographique selon les revendications 1 et 8, caractérisé en ce que la couche générant les porteurs de charge est sensible à une radiation actinique ayant une longueur d'onde supérieure à 390nm et en ce que la couche de transport de porteurs de charge est transparente à cette radiation.
12. Utilisation du matériau d'enregistrement électrophotographique selon l'une quelconque des revendications 1 à 11 dans un procédé de reproduction électrophotographique.
EP78101087A 1977-10-17 1978-10-06 Matériau électrophotographique et son application dans des procédés d'enregistrement Expired EP0001599B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/842,431 US4150987A (en) 1977-10-17 1977-10-17 Hydrazone containing charge transport element and photoconductive process of using same
US842431 1992-03-04

Publications (2)

Publication Number Publication Date
EP0001599A1 EP0001599A1 (fr) 1979-05-02
EP0001599B1 true EP0001599B1 (fr) 1981-10-21

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US (1) US4150987A (fr)
EP (1) EP0001599B1 (fr)
JP (1) JPS5459143A (fr)
AR (1) AR222158A1 (fr)
AU (1) AU520312B2 (fr)
CA (1) CA1108914A (fr)
DE (1) DE2861209D1 (fr)

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US4150987A (en) 1979-04-24
AR222158A1 (es) 1981-04-30
AU3719478A (en) 1979-12-20
AU520312B2 (en) 1982-01-28
CA1108914A (fr) 1981-09-15
JPS5459143A (en) 1979-05-12

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