EP0001599A1 - Matériau électrophotographique et son application dans des procédés d'enregistrement - Google Patents
Matériau électrophotographique et son application dans des procédés d'enregistrement Download PDFInfo
- Publication number
- EP0001599A1 EP0001599A1 EP78101087A EP78101087A EP0001599A1 EP 0001599 A1 EP0001599 A1 EP 0001599A1 EP 78101087 A EP78101087 A EP 78101087A EP 78101087 A EP78101087 A EP 78101087A EP 0001599 A1 EP0001599 A1 EP 0001599A1
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- EP
- European Patent Office
- Prior art keywords
- recording material
- charge
- transport layer
- electrophotographic recording
- charge carrier
- 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.)
- Granted
Links
- 0 *Nc1ccccc1 Chemical compound *Nc1ccccc1 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N CN1CCOCC1 Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0616—Hydrazines; Hydrazones
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
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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
- G03G5/0624—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
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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
Definitions
- the invention relates to an electrophotographic recording material 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 3 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 solution. The discharged areas of the element show no affinity of this kind for the toner. The sc-formed toner image is then transferred to another surface, for example on paper, and is fixed on this by pressure- or heat-sensitive or similar additives that are added to the toner.
- a particularly advantageous electrophotographic element is obtained when a layer which generates charge carriers and which is sensitive to actinic radiation to form 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 charge carrier transport layer is not sensitive to actinic radiation under the conditions used, but it serves to remove positive charges from the charge carrier generating layer either . depending on the system used, to the surface of the negatively charged charge carrier transport layer on which the image is formed, or in a system with a positive charge to the conductive base.
- 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 of a type other than that of the present invention have already been used as a radiation-sensitive material in photoconductive layers.
- U.S. Patent No. 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 generation layer and a charge transport layer which has a charge transport layer containing a hydrazone bath, as characterized in the claims, and a polymer binder.
- p-diethylaminobezaldehyde (diphenylhydranzone).
- Other preferred carrier transport materials are o-ethoxy-p-diethyl-inobenzaldehyde (diphenylhydrazone), o-methyl-p-diethylami-topzaldehyde (diphenyhydrazone), o-methyl-p-dimethylaminobenzadehyde (diphenylhydrazone), p- dipropylaminobenzaldehyde (dipenylhydrazone), p-diethylaminobenzalde hyd- (benzylphenylhydrazone), p -dibutylaminobenzaldehyde- (diphenylhydrazone) and p-dimethylaminobenzaldehyde- (diphenylhydrazone).
- Multi-layer electrophotographic recording materials are generally known.
- the charge carrier-generating layer which can consist of an organic or inorganic material, is sensitive to actinic radiation which strikes the material to form electron-hole pairs.
- 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 sulfo selenide.
- Materials which generate organic charge carriers include cyanine compounds, which are described, for example, in German patent application P 22 15 040.9, disazo compounds, which are described, for example, in German patent applications P 22 15 968.1 and P 26 35 887.2, or phthalocyanine compounds. Useful results are also obtained with charge generating materials that Methine dye derivatives of squaric acid include. Materials of this type are discussed in German patent application P 24 01 220.2.
- 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 "- naphthanilide] 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 essentially 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. is 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 approximately 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.
- a particularly preferred charge carrier transport material is p-diethylaminobenzaldehyde (diphenylhydrazone):
- Trans p are o-ethoxy-p-diäthylaminobenzaldehyd- (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 from Rohm and Haas under the designation A-11.
- 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 g in Fi. 1 is generally identified by reference number 10.
- the recording material 10 comprises a charge generation layer 12 and a charge transport layer 14. As shown, a negative charge is on the surface of the charge transport layer 14. A positive charge is on the opposite side of the charge generation layer 12, ie 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 terms of the negative charge on it made of an insulating mate rial. 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.
- the recording material 10 in FIG. 1 can also be exposed to actinic radiation from the opposite side, ie through the layer support.
- a backing suitable for the present invention was made 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 poly ester 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 produced 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 material was tested by charging the surface to -870 volts in the dark, the charged electrophotographic material with light used in commercial electrophotographic equipment under various conditions of light intensity and by determining the light intensity required to discharge the recording material to a voltage of -150 volts within 454 ms under the specified conditions. It was found that 1.10 ⁇ J / 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 have been tested in commercial copiers and have given excellent results in terms of charge transport, resistance to toner filming, physical resistance to wear, long-term stability of electrical and physical properties and low temperature operation.
- Multilayered electrophotographic Aufzeichnun g smateria- lien which are prepared in Example 1 similar to that made with different resins in different amounts in the charge carrier 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 E-diethylaminobenzaldehyde (diphenylhydrazone).
- the recording material was tested as in Example 1, it was found that 3.0 ⁇ J / 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 .
- 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 ⁇ J / 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.
- 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 ⁇ J / cm 2 were required.
- Multilayer electrophotographic recordings similar to that prepared in Example 2e were made except that 5.78 g of p-diethylaminobenzaldehyde (diphenylhydrazone) was used in the charge transport layer solution in Example 7a and 7.27 g in Example 7b.
- p-diethylaminobenzaldehyde diphenylhydrazone
- a multilayer electrophotographic recording medium similar to that of Example 2a was made except that 13.5 g of p-diethylaminobenzaldehyde (diphenylhydrazone) was dissolved in the solution of the Laduna carrier trans port layer were used.
- p-diethylaminobenzaldehyde diphenylhydrazone
- 1.37 ⁇ J / 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 material 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
- a multilayered electrophotographic recording materials which were similar to that given in Example 2 were prepared with the exception that 13.5 g of the following hydrazones in the solution of the charge carrier-p were used ort harsh:
- Multilayer electrophotographic recording materials similar to that in Example 1 were prepared with the exception that the solution of the charge carrier transport layer contained 6.75 g of polyester resin, 6.75 g of polycarbonate resin and 13.5 g of the hydrazone compounds given 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 in accordance with the present invention was prepared by meniscus coating the carrier-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 ⁇ J / 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 multi-layer electrophotographic recording material similar to that in Example 13 was prepared except that the charge generation 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 ⁇ J / cm 2 of light energy was required to discharge the recording material from a voltage in the dark from -870 to -150 V with a response time to exposure of 116 ms.
- a multilayered electrophotographic recording material similar to that in Example 13 was prepared except that the carrier generation layer solution was 0.15 g of hydroxysquarylium and 0.15 g Methylsquarylium and the solution of the charge carrier transport layer contained 8.12 g of polycarbonate resin and 5.42 g of p-diethylaminobenzaldehyde (diphenylhydrazone).
- the carrier generation layer solution was 0.15 g of hydroxysquarylium and 0.15 g Methylsquarylium
- the solution of the charge carrier transport layer contained 8.12 g of polycarbonate resin and 5.42 g of p-diethylaminobenzaldehyde (diphenylhydrazone).
- 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-diethylaminobeazalde to a charge-generating layer which was produced by vacuum deposition of selenium and tellurium - hyd (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-diethylaminobeazalde
- the p-type charge carrier transport layer according to the present invention can be produced with various types of scavengers as well as a large number 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 when used in relatively high concentrations, tend to crystallize, thereby reducing their charge carriers transport function decreases. 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, especially at low temperatures, to adhesive. to neighboring layers and resistance to mechanical wear at different temperatures.
- the recording materials also show excellent properties with regard to aging and have a considerable resistance to toner formation.
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- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
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 true EP0001599A1 (fr) | 1979-05-02 |
EP0001599B1 EP0001599B1 (fr) | 1981-10-21 |
Family
ID=25287276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78101087A Expired EP0001599B1 (fr) | 1977-10-17 | 1978-10-06 | Matériau électrophotographique et son application dans des procédés d'enregistrement |
Country Status (7)
Country | Link |
---|---|
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) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2426281A1 (fr) * | 1978-05-17 | 1979-12-14 | Mitsubishi Chem Ind | Plaque electrophotographique |
DE3020108A1 (de) * | 1979-05-28 | 1980-12-11 | Ricoh Kk | Elektrophotographisches element |
FR2471625A1 (fr) * | 1979-12-08 | 1981-06-19 | Ricoh Kk | Element electrophotographique constitue d'un substrat conducteur et d'une couche photosensible contenant un derive d'hydrazone |
DE3150068A1 (de) * | 1980-12-17 | 1982-07-22 | Canon K.K., Tokyo | Lichtempfindliches element fuer elektrophotografische zwecke |
DE3124396A1 (de) * | 1980-06-24 | 1982-07-22 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Elektrophotographischer photorezeptor |
DE3150265A1 (de) * | 1980-12-19 | 1982-08-26 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Elektrophotographisch empfindliche materialien |
DE3245637A1 (de) * | 1981-12-09 | 1983-06-16 | Canon K.K., Tokyo | Lichtempfindliches element fuer elektrofotografische zwecke |
EP0084147A2 (fr) * | 1982-01-16 | 1983-07-27 | BASF Aktiengesellschaft | Phénylhydrazones et leur utilisation |
US4410615A (en) * | 1980-10-23 | 1983-10-18 | Konishiroku Photo Industry Co., Ltd. | Layered electrophotographic photosensitive element having hydrazone charge transport layer |
US4415640A (en) * | 1981-02-19 | 1983-11-15 | Konishiroku Photo Industry Co., Ltd. | Electrophotographic element with fluorenylidene hydrazone compounds |
EP0069397B1 (fr) * | 1981-07-07 | 1985-02-20 | Mitsubishi Kasei Corporation | Plaque électrophotographique |
EP0366308A2 (fr) * | 1988-10-28 | 1990-05-02 | Lexmark International, Inc. | Photoconducteurs organiques ayant une fatigue diminuée |
FR2647563A1 (fr) * | 1989-05-27 | 1990-11-30 | Japat Ltd | Photorecepteur electrophotographique, et composes et composition le constituant |
US8268457B2 (en) | 2006-06-05 | 2012-09-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device and material for organic electroluminescent device |
Families Citing this family (270)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5546760A (en) * | 1978-09-29 | 1980-04-02 | Ricoh Co Ltd | Electrophotographic photoreceptor |
JPS5552063A (en) * | 1978-10-13 | 1980-04-16 | Ricoh Co Ltd | Electrophotographic receptor |
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FR2471625A1 (fr) * | 1979-12-08 | 1981-06-19 | Ricoh Kk | Element electrophotographique constitue d'un substrat conducteur et d'une couche photosensible contenant un derive d'hydrazone |
DE3046240A1 (de) * | 1979-12-08 | 1981-09-17 | Ricoh Co., Ltd., Tokyo | Elektrophotographisches element |
DE3124396A1 (de) * | 1980-06-24 | 1982-07-22 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Elektrophotographischer photorezeptor |
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DE3150068A1 (de) * | 1980-12-17 | 1982-07-22 | Canon K.K., Tokyo | Lichtempfindliches element fuer elektrophotografische zwecke |
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DE3245637C2 (fr) * | 1981-12-09 | 1990-02-01 | Canon K.K., Tokio/Tokyo, Jp | |
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EP0084147A2 (fr) * | 1982-01-16 | 1983-07-27 | BASF Aktiengesellschaft | Phénylhydrazones et leur utilisation |
EP0084147A3 (en) * | 1982-01-16 | 1984-09-05 | Basf Aktiengesellschaft | Phenyl hydrazones and their use |
EP0366308A2 (fr) * | 1988-10-28 | 1990-05-02 | Lexmark International, Inc. | Photoconducteurs organiques ayant une fatigue diminuée |
EP0366308A3 (fr) * | 1988-10-28 | 1991-04-03 | Lexmark International, Inc. | Photoconducteurs organiques ayant une fatigue diminuée |
FR2647563A1 (fr) * | 1989-05-27 | 1990-11-30 | Japat Ltd | Photorecepteur electrophotographique, et composes et composition le constituant |
US8268457B2 (en) | 2006-06-05 | 2012-09-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device and material for organic electroluminescent device |
Also Published As
Publication number | Publication date |
---|---|
DE2861209D1 (en) | 1981-12-24 |
AU3719478A (en) | 1979-12-20 |
AU520312B2 (en) | 1982-01-28 |
JPS5542380B2 (fr) | 1980-10-30 |
AR222158A1 (es) | 1981-04-30 |
EP0001599B1 (fr) | 1981-10-21 |
US4150987A (en) | 1979-04-24 |
JPS5459143A (en) | 1979-05-12 |
CA1108914A (fr) | 1981-09-15 |
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