EP0002238B1 - Elektrophotographische Elemente und Verfahren zu ihrer Herstellung - Google Patents

Elektrophotographische Elemente und Verfahren zu ihrer Herstellung Download PDF

Info

Publication number
EP0002238B1
EP0002238B1 EP19780101449 EP78101449A EP0002238B1 EP 0002238 B1 EP0002238 B1 EP 0002238B1 EP 19780101449 EP19780101449 EP 19780101449 EP 78101449 A EP78101449 A EP 78101449A EP 0002238 B1 EP0002238 B1 EP 0002238B1
Authority
EP
European Patent Office
Prior art keywords
dye
layer
electrophotographic
photoconductive
layers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP19780101449
Other languages
English (en)
French (fr)
Other versions
EP0002238A1 (de
Inventor
Jerome Howard Perlstein
George Arthur Reynolds
James Albert Vanallan
Suzanne Patricia Clark
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0002238A1 publication Critical patent/EP0002238A1/de
Application granted granted Critical
Publication of EP0002238B1 publication Critical patent/EP0002238B1/de
Expired legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, 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
    • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
    • 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

Definitions

  • This invention relates to electrophotography and particularly to an electrophotographic element and a method of enhancing the spectral sensitivity and image resolution of an electrophotographic element.
  • One type of electrophotographic element particularly useful in electrophotography employs a layer containing a photoconductive material and an electrically insulating, film-forming, resinous binder.
  • an electrophotographic element In many uses, it is desirable for an electrophotographic element to exhibit high speed (as measured by an electrophotographic speed or characteristic curve), a low residual potential after exposure, and resistance to electrical fatigue. Sometimes it is also desirable that the electrophotographic element be capable of accepting a high surface potential and have a low rate of dark decay.
  • High speed electrophotographic elements which exhibit many of the desirable qualities mentioned above have been developed. Such high speed elements are referred to as “aggregate” or “heterogeneous” elements, and are described in U.S. Patent 3,615,414 issued October 26, 1971 to Light, and U.S. Patent 3,732,180 issued May 8, 1973 to Gramza et al.
  • the "aggregate” electrophotographic elements of these patents comprise one or more photoconductive layers which contain a continuous polymer phase having dispersed therein co-crystalline particles of a pyrylium or thiapyrylium salt and a polymer.
  • a dope consisting of a photoconductor and a sensitizer initially dissolved in dichloromethane as well as a binder is used.
  • the dope is then coated on a support and dried.
  • the coated product is suitable for use in a standard xerographic process.
  • the present invention provides an electrophotographic element and method for enhancing both spectral sensitivity and image resolution.
  • the electrophotographic element comprises, on a conductive support, a layer containing an electrically insulating binder, an organic photoconductor and a dye wherein said dye is in the form of a dye-dye complex, said dye having the formula: wherein
  • die-dye complex is used herein to refer to the condition of the dye in the electrophotographic element prepared according to the method of the invention. Although the nature of the combination of the dye molecules with each other is not certain, the observed facts indicate that the dye molecules are present in a close molecular relationship with each other which differs distinctly from co-crystalline dye-polymer "aggregate" of the prior art. Hence the name “dye-dye complex” is used herein to identify the condition of the dye in our novel element.
  • electrophotographic elements which contain one or more of the dyes described herein surprisingly exhibit enhanced speed, as compared to an element which is otherwise identical, but which has not been treated to produce the "dye-dye complex" condition.
  • the electrophotographic elements of this invention also exhibit a better relationship of speed and image resolution (referred to herein as "speed-resolution product"), as compared with many electrophotographic elements of the prior art.
  • speed-resolution product Such improved properties of the dye in our electrophotographic elements are believed due to its molecular relationship and not to the particular method by which such relationship is achieved.
  • the drawing shows the absorption spectrum of a photoconductive layer containing a binder and one of the dyes which we have discovered can be transformed to the "dye-dye complex" condition.
  • transformed photoconductive layer is intended to mean a photoconductive layer of an electrophotographic element prepared according to the method of this invention which contains dye in the "dye-dye complex” conditions as described herein.
  • the electrophotographic elements prepared according to the method of this invention are readily distinguishable from the so-called "aggregate” photoconductive elements of the prior art.
  • the photoconductive layers of the electrophotographic elements prepared according to this invention have dye in the "dye-dye complex” condition, whereas "aggregate” photoconductive layers contain dye in a "dye-polymer interaction” condition.
  • Dyes useful in "aggregate” photoconductive layers react with a polymer in the layer, and are polymer-dependent (i.e. only certain polymers can be used to produce the "dye-polymer interaction" product).
  • the photoconductive layers of this invention contain dyes which are not dependent upon a particular type of poymer for their valuable electrophotographic properties, and are therefore "polymer-independent".
  • the absorption spectra of the pyrylium dye salts used to form the aforementioned "aggregate" photoconductive layers also change when a binderless coating of such dye salts is treated with solvent vapors.
  • the absorption spectra of vapor-treated layers comprising an electrically insulating binder polymer and the aforementioned pyrylium dyes are different from that of a vapor-treated binderless coating of the pyrylium dye.
  • Useful dyes within the scope of general Formula I include the dyes shown in Table I.
  • the photoconductive layers of the electrophotographic elements as prepared according to the method of the present invention are transformed photoconductive layers comprising a dye as previously described and an electrically insulating binder.
  • the transformation is the result of solvent action on the dye.
  • the transformation can be carried out as follows: A solution containing the selected dye, the electrically insulating polymer and an organic photoconductor is coated onto a suitable support. The solvent is then evaporated. Transformation of the dye is then achieved by contact of the resulting layer with the vapors of solvent until a color change in the layer occurs. Similarly, coating such a layer from a solvent mixture which also contains solvent which persists in the coating during drying results in the desired transformation.
  • the photoconductive layers of the examples have been prepared by mixing together separate solutions of the selected dye and the electrically insulating polymer and then adding an organic photoconductor.
  • the resulting coating solution is then coated on a conductive support, such as a nickel-coated poly(ethylene terephthalate) film support, and dried in air or under vacuum at about 60°C for about one hour.
  • the coated layer is then treated with a solvent vapor for a few minutes and then redried under vacuum for about one hour at about 60°C.
  • the organic solvents useful for preparing coating solution can be selected from a variety of solvents.
  • Useful solvents include organic hydrocarbon solvents, with preferred solvents being halogenated hydrocarbon solvents.
  • the requisite properties of the solvent are that it be capable of dissolving the selected dye and be capable of dissolving or at least highly swelling or solubilizing the polymer in the layer.
  • the solvent is volatile, preferably having a boiling point of less than 200°C.
  • Particularly useful solvents include halogenated lower alkanes having from 1 to 3 carbon atoms.
  • the solvents useful in achieving the desired transformation of dye include, among others, dichloromethane, toluene, tetrahydrofuran, p-dioxane, chloroform and 1,1,1-trichloroethane. Such solvents may be used alone or in combination with other volatile organic liquids.
  • the desired transformation is indicated by a change in the absorption spectrum of the photoconductive layer.
  • the amount of the selected dye incorporated into photoconductive layers and elements of the present invention can be varied over a relatively wide range.
  • the dye may be present in an amount of 0.01 to 50.0 percent by weight of the coated layer on a dry basis.
  • the photoconductive layer includes an organic photoconductor, useful results are obtained by using the dye in amounts of 0.1 to 30 percent by weight of the photoconductive layer.
  • the upper limit of the amount of dye is a matter of choice and the amount of any dye used will vary widely depending on the particular dye selected, the electrophotographic response desired, the proposed structure of the photoconductive element and the mechanical properties desired in the element.
  • Conventional electrically insulating film-forming polymers are useful in the present invention.
  • Such polymers include polystyrene, polyvinylethers, polyolefins, polythiocarbonates, polycarbonates, and phenolic resins such as those disclosed in U.S. Patent 3,615,414. Mixtures of such polymers are also useful.
  • Particularly useful polymers have recurring units as shown in Table II.
  • Useful organic photoconductors are generally electron acceptors or electron donors for the dyes. They include the organic photoconductors described in the patent literature such as those disclosed in U.S. Patent 3,615,414; U.S. Patent 3,873,311; U.S. Patent 3,873,312 and Research Disclosure 10938, Volume 109, May 1973. Aromatic amines such as tri-p-tolylamine and (di-p-tolylamino- phenyl)cyclohexane are particularly useful.
  • organic photoconductors when used, are present in our photoconductive layers in an amount equal to at least 1 weight percent of the combined dry weight of dye, binder, and organic photoconductor in the layer(s).
  • the organic photoconductor can be present in the layer up to the limit of its solubility in the polymeric binder.
  • a polymeric organic photoconductor may also be employed either as the binder or with another polymeric binder.
  • a preferred weight range for the organic photoconductor in the photoconductive layer is from 10 to 40 weight percent.
  • a wide variety of electrically conducting supports can be used in the practice of this invention, for example, paper (at a relative humidity above 20 percent); aluminum-paper laminates; metal foils such as aluminum foil, zinc foil, etc.; metal plates such as aluminum, copper, zinc, brass and galvanized plates; vapor-deposited metal layers such as silver, chromium, nickel, aluminum, cermet materials and the like coated on paper.
  • Conventional photographic film bases such as cellulose acetate, poly(ethyleneterephthalate) or polystyrene can also be used.
  • Conducting materials such as nickel can be vacuum deposited on transparent film supports in sufficiently thin layers to allow electrophotographic elements prepared therewith to be exposed from either side of such elements.
  • An especially useful conducting support can be prepared by coating a film of poly(ethylene terephthalate) with a conducting layer containing a semiconductor dispersed in a resin.
  • the photoconductive layers can be coated, if desired, directly on a conducting substrate.
  • Such subbing layers typically have a dry thickness in the range of 0.1 to 5 micrometers.
  • Optional overcoat layers may be used in the present invention.
  • the surface layer of the element of the invention may be coated with one or more electrically insulating, organic polymer coatings or electrically insulating, inorganic coatings.
  • electrically insulating, organic polymer coatings or electrically insulating, inorganic coatings are well known in the art.
  • Typical useful overcoats are disclosed, for example, in Research Disclosure "Electrophotographic Elements, Materials, and Processes", Volume 109, page 63, Paragraph V, May, 1973.
  • Coating thickness of the phtoconductive layer on the support can vary widely. Normally, a coating in the range of about 0.5 ⁇ m to about 300 ⁇ m before drying is useful for the practice of this invention. The preferred range of coating thickness is found to be in the range from about 1.0 ⁇ m to about 150 ⁇ m before drying, although useful results can be obtained outside of this range. The resultant dry thickness of the coating is preferably between 2 pm and 50 pm, although useful results can be obtained with a dry coating thickness between 1 and 200 ⁇ m.
  • the symbol @ stands for registered Trade Mark.
  • the elements of the present invention can be employed in any of the well-known electrophotographic processes which require photoconductive layers.
  • One such process is the xerographic process.
  • the following examples are included for a further understanding of the invention.
  • the untreated film appeared blue-green by transmitted light. Upon solvent treatment for one minute with the vapors of methylene chloride, the film turned blue.
  • the optical absorption spectrum for this film before and after vapor treatment is shown in the drawing.
  • the absorption spectrum was determined in a conventional manner using a Cary 14 spectrophotometer.
  • the absorption spectrum 1 for the untreated film had a peak at about 650 nm and a shoulder at 600 nm.
  • the spectrum 2 for the methylene chloride treated film is shifted with narrow peaks at 635 nm and 560 nm.
  • the untreated film did not have a peak at 560 nm.
  • the photosensitivity of each sample was determined as follows: the surface of the layer away from the support was electrostatically charged negatively under a corona source until the surface potential as measured by a capacitively-coupled probe attached to an electrometer attained an initial dark value, V o of -500 volts. The rear surface of the charged element was then exposed to monochromatic visible radiation at a wavelength of 650 nm. The exposure caused reduction of the surface potential of the element from -500 volts to -100 volts.
  • the photosensitivity of the element can be considered equivalent to the exposure in ergs/cm 2 necessary to discharge the element from -500 to -100 volts, after correction for light absorption and reflection by the film support.
  • a photoconductive layer containing dye 2 (Table I) was tested as in Example I. Upon vapor treatment the layer changed from blue-green to blue and exhibited the same absorption and speed characteristics as dye 1 (Table I).
  • Element A contained a homogenous photoconductive layer of the type described in U.S. Patent 3,542,547.
  • Element B contained an "aggregate" photoconductive layer of the type described in U.S. Patent 3,873,311.
  • Elements C and D are of this invention and contain dye 1 in their photoconductive layers (Table I). These layers contained the following materials.
  • Each coating solution was made 24 hours prior to the coating step by dissolving the components in the order listed and allowing sufficient time between additions for complete solvation.
  • Each solution was coated on a transparent nickel or cuprous iodide conductive support.
  • Layer A was made at a coverage of 7.5 gms/m2.
  • Layer B was made at a coverage of 11.3 gms/m 2 .
  • Layers C and D were made at a coverage of 7.5 gms/m2. (Coverages are in terms of dry basis.) The coatings were then dried.
  • Photosensitivity and resolution data are presented in Table III. Photosensitivity was determined as in Example I for negative charging at a wavelength where the optical density of the film equals 1.0. Discharge was from -600V to -1 OOV. The data in this table shows that electrophotographic elements of the present invention have a higher speed-resolution product than the photoconductive elements of A and B which are representative of the prior art.

Landscapes

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

Claims (5)

1. Verfahren zur Steigerung der spektralen Empfindlichkeit und des Bildauflösungsvermögens eines elektrophotographischen Elements mit einem leitfähigen Träger und einer hierauf befindlichen Schicht, die ein elektrisch isolierendes Bindemittel, einen organischen Photoleiter und einen Farbstoff enthält, der in Form eines Farbstoff-Farbstoff-Komplexes vorliegt und folgender Formel entspricht:
Figure imgb0013
in der Xe ein Anion darstellt, bei dem man (1) die Schicht auf den Träger aus einer organischen Lösungsmittel-Mischung aufträgt, die ein Lösungsmittel für den Farbstoff enthält, das während der Trocknung in der Beschichtung bleibt oder bei dem man (2) das Element der Einwirkung der Dämpfe eines organischen Lösungsmittels für den Farbstoff aussetzt, bis eine Farbveränderung auftritt, worauf man das Element trocknet.
2. Verfahren nach Anspruch 1, bei dem die organische Lösungsmittel-Mischung Kohlenwasserstoffe, halogenierte Kohlenwasserstoffe, p-Dioxan und halogenierte aliphatische Alkohole enthält.
3. Verfahren nach Anspruch 2, bei dem in der Lösungsmittel-Mischung enthaltene Lösungsmittel Siedepunkte von weniger als 200°C aufweisen.
4. Verfahren nach Anspruch 1, bei dem der Farbstoff besteht aus: 4 - [2,6 - Diphenyl - 4H - thiapyran - 4 - yliden) - methyl] - 2,6 - diphenylthiapyryliumperchlorat oder 4 - [2,6 - diphenyl - 4H - thiapyran - 4 - yliden)methyl] - 2,6 - diphenylthiapyryliumfluoroborat.
5. Elektrophotographisches Element mit einem leitfähigen Träger, einer Schicht mit einem elektrisch isolierenden Bindemittel, einem organischen Photoleiter und einem Farbstoff, wobei der Farbstoff in Form eines Farbstoff-Farbstoff-Komplexes vorliegt und der Farbstoff der folgenden Formel entspricht:
Figure imgb0014
in der Xe für ein Anion steht.
EP19780101449 1977-11-28 1978-11-24 Elektrophotographische Elemente und Verfahren zu ihrer Herstellung Expired EP0002238B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US85514177A 1977-11-28 1977-11-28
US87497178A 1978-02-03 1978-02-03
US874971 1986-06-16
US855141 2004-05-27

Publications (2)

Publication Number Publication Date
EP0002238A1 EP0002238A1 (de) 1979-06-13
EP0002238B1 true EP0002238B1 (de) 1984-06-13

Family

ID=27127279

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19780101449 Expired EP0002238B1 (de) 1977-11-28 1978-11-24 Elektrophotographische Elemente und Verfahren zu ihrer Herstellung

Country Status (4)

Country Link
EP (1) EP0002238B1 (de)
JP (1) JPS5483837A (de)
CA (1) CA1129426A (de)
DE (1) DE2862416D1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8273509B2 (en) 2006-01-06 2012-09-25 Mitsubishi Chemical Corporation Electrophotographic photoreceptor, and image forming device and electrophotographic photoreceptor cartridge using the same member cartridge

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4327169A (en) * 1981-01-19 1982-04-27 Eastman Kodak Company Infrared sensitive photoconductive composition, elements and imaging method using trimethine thiopyrylium dye
JPS6377933A (ja) * 1986-09-22 1988-04-08 Daicel Chem Ind Ltd ポリカ−ボネ−ト樹脂光学成型品
EP2154575B1 (de) * 2004-07-16 2014-12-24 Mitsubishi Chemical Corporation Elektrofotografischer Fotoempfänger
JP4847245B2 (ja) * 2005-08-15 2011-12-28 キヤノン株式会社 電子写真感光体、プロセスカートリッジおよび電子写真装置
JP4847305B2 (ja) * 2005-12-20 2011-12-28 キヤノン株式会社 電子写真感光体、プロセスカートリッジおよび電子写真装置
JP4862662B2 (ja) * 2006-01-13 2012-01-25 三菱化学株式会社 電子写真感光体並びにそれを用いた画像形成装置及び電子写真カートリッジ
JP5040319B2 (ja) * 2006-01-13 2012-10-03 三菱化学株式会社 正帯電型電子写真感光体、画像形成装置、画像形成方法及び電子写真感光体カートリッジ
JP2007213050A (ja) * 2006-01-13 2007-08-23 Mitsubishi Chemicals Corp 画像形成装置
JP5040318B2 (ja) * 2006-01-13 2012-10-03 三菱化学株式会社 感光層形成用塗布液、電子写真感光体、電子写真感光体カートリッジ及び画像形成装置
JP4862661B2 (ja) * 2006-01-13 2012-01-25 三菱化学株式会社 感光層形成用塗布液、電子写真感光体、電子写真感光体カートリッジ及び画像形成装置
JP4862660B2 (ja) * 2006-01-16 2012-01-25 三菱化学株式会社 電子写真感光体
JP4847251B2 (ja) * 2006-03-10 2011-12-28 キヤノン株式会社 電子写真感光体、プロセスカートリッジおよび電子写真装置
JP2007298952A (ja) * 2006-04-06 2007-11-15 Canon Inc 電子写真感光体、電子写真感光体の製造方法、プロセスカートリッジ及び電子写真装置
JP4847247B2 (ja) * 2006-07-31 2011-12-28 キヤノン株式会社 電子写真感光体の製造方法
JP4878237B2 (ja) * 2006-07-31 2012-02-15 キヤノン株式会社 電子写真感光体の製造方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UST904032I4 (en) * 1972-11-21 Defensive publication
BE613738A (de) * 1961-04-07
USRE28698E (en) * 1970-03-13 1976-01-27 Matsushita Electric Industrial Co., Ltd. Electrophotographic material containing sensitizers
FR2105830A5 (en) * 1970-08-03 1972-04-28 Eastman Kodak Co Electrophotographic sensitisers - bispyrylium salts for org photo conductors increased sensitivity
JPS512376B1 (de) * 1971-04-30 1976-01-26
US3938994A (en) * 1972-03-17 1976-02-17 Eastman Kodak Company Pyrylium dyes for electrophotographic composition and element

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8273509B2 (en) 2006-01-06 2012-09-25 Mitsubishi Chemical Corporation Electrophotographic photoreceptor, and image forming device and electrophotographic photoreceptor cartridge using the same member cartridge

Also Published As

Publication number Publication date
EP0002238A1 (de) 1979-06-13
JPS5483837A (en) 1979-07-04
DE2862416D1 (en) 1984-07-19
JPS6248214B2 (de) 1987-10-13
CA1129426A (en) 1982-08-10

Similar Documents

Publication Publication Date Title
US4327169A (en) Infrared sensitive photoconductive composition, elements and imaging method using trimethine thiopyrylium dye
EP0002238B1 (de) Elektrophotographische Elemente und Verfahren zu ihrer Herstellung
US5830614A (en) Multilayer organic photoreceptor employing a dual layer of charge transporting polymers
EP0289216B1 (de) Elektrophotographisches Element
EP0104092B1 (de) Elektrostatographisches Bildelement
US5017449A (en) Electrophotographic photosensitive member with substituted nylon interlayer
US5190817A (en) Photoconductive recording element
US4106934A (en) Photoconductive compositions and elements with charge transfer complexes
US5372904A (en) Photoreceptor with improved charge blocking layer
EP0473448B1 (de) Elektrofotografisches Aufzeichnungselement
US4105447A (en) Photoconductive insulating compositions including polyaryl hydrocarbon photoconductors
US5316880A (en) Photoreceptor containing similar charge transporting small molecule and charge transporting polymer
EP0759579A1 (de) Elektrophotographische Elemente, die Ladungstransportschichten bestehend aus Polyesterharzen mit hoher Ladungsträgerbeweglichkeit enthalten
EP0572726B1 (de) Photoleitfähiges Aufzeichnungsmaterial mit vernetztem Bindemittel in der Ladungen erzeugenden Schicht
US5310613A (en) High sensitivity visible and infrared photoreceptor
EP0643846B1 (de) Photoleitfähiges aufzeichnungsmaterial mit vernetztem bindemittelsystem
US4066455A (en) Selenium containing multi-active photoconductive element
CA1098360A (en) Multilayer photoconductive element
US5288573A (en) Photoconductive elements which are sensitive to near-infrared radiation
US5698359A (en) Method of making a high sensitivity visible and infrared photoreceptor
US4927726A (en) Photoreceptor with polynuclear bisoxazole or bisthizole
US20090297968A1 (en) Zirconocene containing photoconductors
US4108657A (en) Multi-active photoconductive element with an aggregate and inorganic photoconductor
US4769304A (en) Photoconductive composition and electro-photographic light-sensitive material using said composition
US6022656A (en) Bipolar electrophotographic elements

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE DE FR GB

17P Request for examination filed
DET De: translation of patent claims
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE DE FR GB

REF Corresponds to:

Ref document number: 2862416

Country of ref document: DE

Date of ref document: 19840719

ET Fr: translation filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19841108

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19841127

Year of fee payment: 7

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19890110

Year of fee payment: 11

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19891124

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19891130

BERE Be: lapsed

Owner name: EASTMAN KODAK CY

Effective date: 19891130

GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19900731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19900801

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST