US3503740A - Photoconductive elements containing organic photoconductors and sensitizers - Google Patents

Photoconductive elements containing organic photoconductors and sensitizers Download PDF

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US3503740A
US3503740A US654092A US3503740DA US3503740A US 3503740 A US3503740 A US 3503740A US 654092 A US654092 A US 654092A US 3503740D A US3503740D A US 3503740DA US 3503740 A US3503740 A US 3503740A
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photoconductive
tropylium
photoconductor
bis
sensitizers
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Roy C De Selms
Charles V Wilson
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • 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
    • G03G5/0605—Carbocyclic compounds
    • G03G5/0607—Carbocyclic compounds containing at least one non-six-membered 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing 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
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0629—Heterocyclic compounds containing one hetero ring being five-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
    • G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom

Definitions

  • This invention relates to electrophotography, and in particular to novel sensitized photoconductive compositions and elements having coated thereon such compositions.
  • the process of xerography employs an electrophotographic element comprising a support material bearing a coating of a normally insulating material whose electrical resistance varies with the amount of incident actinic radiation it receives during an imagewise exposure.
  • the element commonly termed a photoconductive element, is first given a uniform surface charge, generally in the dark after a suitable period of dark adaptation. It is then exposed to a pattern of actinic radiation which has the effect of differentially reducing the potential of the surface charge in accordance with the relative energy contained in various parts of the radiation pattern. The differential surface charge or electrostatic latent image remaining on the electrophotographic element is then made visible by contacting the surface with a suitable electroscopic marking material.
  • marking material or toner whether contained in an insulating liquid or on a dry carrier, can be deposited on the exposed surface in accordance with either the charge pattern or in the absence of charge pattern as desired.
  • the deposited marking material may then be either permanently fixed to the surface of the sensitive element by known means such as heat, pressure, solvent vapor, or the like, or transferred to a second element to which it may similarly be fixed.
  • the electrostatic latent image can be transferred to a second element and a developed there.
  • Various photoconductive insulating materials have been employed in the manufacture of electrophotographic elements. For example, vapors of selenium and vapors of selenium alloys deposited on a suitable support and particles of photoconductive zinc oxide held in a resinous, film-forming binder have found wide application in present-day document copying applications.
  • the organic photoconductors comprising the materials described are inherently light sensitive, their degree of sensitivity is usually low and in the short wave length portion of the spectrum so that it is common practice to add materials to increase the speed and to shift the sensitivity toward the longer wave length portion of the visible spectrum.
  • Increasing the speed and shifting the sensitivity of such systems into the visible regions of the spectrum has several advantages: it makes available inexpensive and convenient light sources such as incandescent lamps; it reduces exposure time; it makes possible the recording of a wide range of colors in proper tonal relationship, and allows projection printing through various optical systems.
  • sensitizers By increasing the speed through the use of sensitizers, photoconductors which would otherwise have been unsatisfactory are useful in processes where high speeds are required such as document copying.
  • some of the sensitizers have appreciably increased the speed of a photoconductive system, they have been unstable when exposed to moisture for a period of time.
  • an object of this invention to provide a novel class of sensitizers for use in combination with certain photoconductors so that improved electrophotographic speeds are obtained.
  • Another object of this invention is to provide novel sensitized photoconductive elements.
  • photoconductive compositions containing a photoconductor and a sensitizer which is a salt of a cycloheptenyl compound.
  • a sensitizer which is a salt of a cycloheptenyl compound.
  • cycloheptenyl compound is meant to include derivatives of cycloheptane, cycloheptene, cycloheptadiene and cycloheptatriene.
  • cycloheptenyl salts of this invention can be sub stituted in the nucleus, if desired, with a wide variety of substituents such as:
  • An aryl radical including substituted and unsubstituted aryl radicals such as phenyl and naphthyl, and particularly phenyl radicals containing amino groups such as alkylamino groups, as well as aryl radicals containing a fused heterocyclic ring,
  • the salt is preferably a perchlorate or fiuoroborate but any anion capable of forming a salt with the cycloheptenyl radical is suitable, e.g., sulfate, chloride, bromide, iodide,
  • the preferred cycloheptenyl salt sensitizers of this irivention are represented by the following structures:
  • E, G and D can be either (a) A phenyl radical
  • X is an anion such as a perchlorate, fluoroborate, sulfate, chloride, bromide or iodide.
  • Typical cycloheptenyl compounds which belong to the herein'described general class of compounds include the following:
  • Electrophotographic elements of the invention can be prepared with any photoconductive compound and the sensitizers of this invention in the usual manner, i.e., by blending a dispersion or solution of the photoconductive compound together with a binder, when necessary or desirable, and coating or forming a self-supporting layer with the photoconductive composition.
  • a suitable amount of the sensitizing compound is mixed with the photoconductive coating composition so that, after thorough mixing, the sensitizing compound is uniformly distributed throughout the desired layer of the coated element.
  • the amount of sensitizer that can be added to a photoconductor-incorporating layer to give effective increases in speed can vary widely. The optimum concentration in any given case will vary with the specific photoconductor and sensitizing compound used.
  • sub stantial speed gains can be obtained where an appropriate sensitizer is added in a concentration range from about 0.0001 to about 30 percent by weight based on the weight of the film-forming coating composition. Normally, a sensitizer is added to the coating composition in an amount from about 0.005 to about 5.0 percentby weight of the total coating composition.
  • the sensitizers of this invention are effective for enhancing the electrophotosensitivity of a wide variety of photoconductors.
  • the preferred photoconductors are those organic compounds which exhibit an electrophotosensitivity to light and are capable of forming transparent elements.
  • An especially useful class of organic photoconductors is referred to herein as organicamine photoconductors.
  • Such organic photoconductors have as a common structural feature at least one amino group.
  • Useful organic photoconductors which can be spectrally sensitized in accordance with this invention include, therefore, arylamine compounds comprising (1) diarylamines such as diphenylamine, dinaphthylamine, N ,N'-diphenylbenzidine,
  • N phenyl 1 naphthylamine N phenyl 2 naphthylamine; N,N diphenyl p phenylenediamine; 2 carboxy 5 chloro 4' methoxydiphenylamine; p anilinophenol; N,N' di 2 naphthyl p phenylenediamine;
  • triarylamines including (a) nonpolymeric triarylamines, such as triphenylamine, N,N,N',N' tetraphenyl m phenylenediamine; 4 acetyltriphenylamine, 4 hexanoyltriphenylamine; 4- lauroyltriphenylamine; 4 hexyltriphenylamine, 4 dodecyltriphenylamine, 4,4 bis(diphenylamino)benzyl, 4,4- bis(diphenylamino)benzophenone, and the like, and (b) polymeric triarylamines such as poly[N,4"-(-N,N',N-triphenylbenzidinefl; polyadipyltriphenylamine, polysebacyltriphenyl
  • A represents a mononuclear or polynuclear divalent aromatic radical, either fused or linear (e.g., phenyl, naphthyl, biphenyl, binaphthyl, etc.), or a substituted divalent aromatic radical of these typeswherein said substituent can comprise a member such as an acyl group having from 1 to about 6 carbon atoms (e.g., acetyl, propionyl, butyryl, etc.), an alkyl group having from 1 to about 6 carbon atoms (e.g., methyl, ethyl, propyl, butyl, etc.), an alkoxy group having from 1 to about 6 carbon atoms (e.g., methoxy, ethoxy, propoxy, pentoxy, etc.), or a nitro group;
  • A represents a mononuclear or polynuclear monovalent aromatic radical, either fused or linear (e.g., phenyl, naphthyl, bi
  • Polyarylalkane photoconductors are particularly useful in producing the present invention. Such photoconductors are described in US. Patent 3,274,000; French Patent 1,383,461 and in copending application of Seus and Goldman titled Photoconductive Elements Containing Organic Photoconductors, filed Apr. 3, 1967. These photoconductors include leuco bases of diaryl or triaryl methane dye salts, 1,1,1-triarylalkanes wherein the alkane moiety has at least two carbon atoms and tetraarylmethanes, there being substituted an amine group on at least one of the aryl groups attached to the alkane and methane moieties of the latter two classes of photoconductors which are non-leuco base materials.
  • Preferred polyaryl alkane photoconductors can be rep resented by the formula:
  • each of D, E and G is an aryl group and I is a hydrogen atom, an alkyl group, or an aryl group, at least one of D, E and G containing an amino substituent.
  • the aryl groups attached to the central carbon atom are preferably phenyl groups, although naphthyl groups can also be used. Such aryl groups can contain such substituents as alkyl and alkoxy typically having 1 to 8 carbon atoms, hydroxy, halogen, etc., in the ortho, meta or para positions, ortho-substituted phenyl being preferred.
  • the aryl groups can also be joined together or cyclized to form a fluorene moiety, for example.
  • each L can be an alkyl group typically having 1 to 8 carbon atoms, a hydrogen atom, an aryl group, or to gether the necessary atoms to form a heterocyclic amino group typically having 5 to 6 atoms in the ring such as morpholino, pyridyl, pyrryl, etc.
  • At least one of D, E, and G is preferably p-dialkylaminophenyl group.
  • I is an alkyl group, such an alkyl group more generally has 1 to 7 carbon atoms.
  • Representative useful polyarylalkane photoconductors include the compounds listed below:
  • Preferred binders for use in preparing the present photoconductive layers comprise polymers having fairly high dielectric strength which are good electrically insulating film-forming vehicles.
  • Materials of this type comprise styrene-butadiene copolymers; silicone resins; styrene-alkyd resins; silicone-alkyd resins; soya-alkyd resins; "poly(vinyl chloride); poly(vinylidene chloride); vinylidene chloride.
  • L acrylonitrile copolymers poly(vinyl acetate); vinyl acetate vinyl chloride copolymers; poly(vinyl acetals), such as poly(vinyl butyral); polyacrylic and methacrylic esters, such as poly(methylmethacrylate), poly(n butylmethacrylate), poly(isobutyl methacrylate),
  • polystyrene nitrated polystyrene
  • polymethylstyrene nitrated polystyrene
  • isobutylene polymers such as poly(ethylenealkaryloxyalkylene terephthalate); phenol formaldehyde resins; ketone resins; polyamide; polycarbonates; polythiocarbonates; poly (ethyleneglycolco bishydroxyethoxyphenyl propane terephthalate); etc.
  • Methods of making resins of this type have been described in the prior art, for example, styrene-alkyd resins can be prepared according to the method described in US. Patents 2,361,019 and 2,258,423.
  • Suitable resins of the type contemplated for use in the photoconductive layers of the invention are sold under such trade names as Vitel PE-101, Cymac, Piccopale 100, Saran F-220 and Lexan 105.
  • Other types of binders which can be used in the photoconductive layers of the invention include such materials as paraffin, mineral Waxes, etc.
  • Solvents of choice for preparing coating compositions of the present invention can include a number of solvents such as benzene, toluene, acetone, Z-butanone, chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, etc., ethers, e.g., tetrahydrofuran, or mixtures of these solvents, etc.
  • solvents such as benzene, toluene, acetone, Z-butanone, chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, etc., ethers, e.g., tetrahydrofuran, or mixtures of these solvents, etc.
  • the photoconductor substance is present in an amount equal to at least about 1 weight percent of the coating composition.
  • the upper limit in the amount of photoconductor substance present can be widely varied in accordance with usual practice. In those cases where a binder is employed, it is normally required that the photoconductor substance be present in an amount from about 1 weight percent of the coating composition to about 99 weight percent of the coating composition.
  • a preferred weight range for the photoconductor substance in the coating composition is from about 10 weight percent to about 60 weight percent.
  • Coating thickness of the photoconductive composition on a support can vary widely. Normally, a coating in the range of about 0.001 inch to about 0.01 inch before drying is useful for the practice of this invention. The preferred range of coating thickness was found to be in the range from about 0.002 inch to about 0.006 inch before drying although useful results can be obtained outside of this range.
  • Suitable supporting materials for coating the photoconductive layers of the present invention can include any of a wide variety of electrically conducting supports, 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 or aluminum and the like.
  • An especially useful conducting support can be prepared by coating a support material such as polyethylene terephthalate with a layer containing a semiconductor dispersed in a resin. Such conducting layers both with and without insulating barrier layers are described in US. Patent 3,245,833.
  • a suitable conducting coating can be prepared from the sodium salt of a carboXyester lactone of maleic anhydride and a vinyl acetate polymer.
  • Such kinds of conducting layers and methods for their optimum preparation and use are disclosed in U.S. 3,007,901 and 3,267,807.
  • 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 aforementioned xerographic process.
  • the electrophotographic element is given a blanket electrostatic charge by placing the same under a corona discharge which serves to give a uniform charge to the surface of the photoconductive layer. This charge is retained by the layer owing to the substantial insulating property of the layer, i.e., the low conductivity of the layer in the dark.
  • the electrostatic charge formed on the surface of the photo-conducting layer is then selectively dissipated from the surface of the layer by exposure to light through an 7 image-bearing transparency by a conventional exposure operation such as, for example, by contact-printing technique, or by lens projection of an image, etc., to form a latent image in the photoconducting layer.
  • a charged pattern is created by virtue of the fact that light causes the charge to be conducted away in proportion to the intensity of the illumination in a particular area.
  • the charge pattern remaining after exposure is then developed, i.e., rendered visible, by treatment with a medium comprising electrostatically attractable particles having optical density.
  • developing electrostatically attractable particles can be in the form of a dust, e.g., powder, a pigment in a resinous carrier, i.e., toner, or a liquid developer may be used in which the developing particles are carried in an electrically insulating liquid carrier.
  • a dust e.g., powder
  • a pigment in a resinous carrier i.e., toner
  • a liquid developer may be used in which the developing particles are carried in an electrically insulating liquid carrier.
  • the present invention is not limited to any particular mode of use of the new electrophotographic materials,
  • the exposure technique, the charging method, the transfer (if any), the developing method, and the fixing method as well as the materials used in these methods can be selected and adapted to the requirements of any particular technique.
  • Electrophotographic materials according to the present invention can be applied to reproduction techniques wherein difierent kinds of radiations, i.e., electromagnetic radiations as well as nuclear radiations, can be used. For this reason, it is pointed out herein that although materials according to the invention are mainly intended for use in connection with methods comprising an exposure, the term electrophotography wherever appearing in the description and the claims, is to be interpreted broadly and understood to comprise both xerography and xeroradiography.
  • EXAMPLE 1 Preparation of tropylium perchlorate To a solution of 6.86 g. (0.02 m.) of triphenylmethyl perchlorate in about 150 ml. of acetonitrile is added 1.84 g. 0.02 m.) of cycloheptatriene. The solvent is removed and the residue triturated with ether. The solid is collected on a filter and recrystallized from acetonitrileethylacetate. The yield is 92% (3.5 g.) and the melting point is greater than 280 C.
  • EXAMPLE 5 Preparation of 5-(Z-methyl-4-diethylaminophenyl)- SH-dibenzo [a,d]tropylium fluoroborate The procedure of Example 3 is followed, using as the starting material 0.1 mole of 3-methyl-N,N-(diethylaniline in place of the N,N-dimethylaniline. The product is obtained in 14 percent yield and has a melting point of 233-235 C. after recrystallization from acetonitrileethyl acetate mixture.
  • compositions are then separately coated on a wet thickness of 0.004 inch on an aluminum surface maintained at 100 F. to provide the coatings described in Table 1 below.
  • the surface of each of the photoconductive layers so prepared is either positively or negatively charged to a potential of about 600 volts under a corona charger.
  • the charged layer is exposed through a stepped density gray scale to the radiation from a 60-watt incandescent lamp at a distance of 100 cm. which provides an illumination-intensity of about 75 meter-candles.
  • the exposure causes reduction of the surface potential of the element under each step of the gray scale from its initial potential, V to some lower potential, V, whose exact value depends upon the actual amount of exposure received by the area.
  • the element is exposed through each step ofthe scale and the resultant surface potential measured.
  • the results of these measurements are plotted on a graph of surface potential V versus log of the exposure for each step.
  • the actual speed of each element is expressed in terms of the reciprocal of the exposure required to reduce the surface potential to any fixed arbitrarily assigned value.
  • the results of these measurements are set forth in the following Table 1.
  • the speed is the quotient of 10 divided by the exposure in meter-candle-seconds required to reduce the potential by 100 volts.
  • the polymeric binder used in the coating compositions is a polyester of terephthalic acid and a mixture of ethylene glycol (1 part by weight) and 2,2-bis(4- hydroxy-ethoxyphenyl) propane (9 parts by weight).
  • the photoconductors referred to in the table are as follows:
  • An electrophotographic element comprising a support having coated thereon a photoconductive composition comprising an organic photoconductor dispersed in a resin binder and a sensitizer having a formula selected from the group consisting of:
  • X is an anion
  • sensitizer is a perchlorate salt of the cycloheptenyl compound.
  • sensitizer is a fluoroborate salt of the cycloheptenyl compound.
  • a photoconductive composition comprising an organic photoconductor dispersed in a resin binder and a sensitizer selected from the group consisting of tropylium perchlorate, (4-dimethy1aminophenyl)-tropyliurn fluoro- 0 borate, 5-(4-dimethylaminophenyl) 5H dibenzo[a,d]
  • tropylium fluoroborate 5-(2-methyl 4 diethylaminophenyD-SH-dibenzo [a,d]tropylium fiuoroborate, 5- (4-dimethylamino1-naphthyl) 5H dibenzo[a,d]tropylium fluoroborate and 5-(9-julolidyl) 5H dibenzo[a,d]tropylium fluoroborate.
  • An electrophotographic element comprising a support having coated thereon the photoconductive composition of claim 4.
  • the electrophotographic element of claim 5 wherein the photoconductor is selected from the group consisting of triphenylamine, 1,3,5-triphenyl 2 pyrazoline, bis(4- diethylamino)-l,l,1-triphenylethane, 4,4 bis(diethy1- amino)-2,2'-dimethyltriphenylmethane, bis(4 diethylamino)tetraphenylmethane, 2,3,4,5 tetraphenylpyrrole and 4,4'-bis(diethylamino)-benzophenone.
  • the photoconductor is selected from the group consisting of triphenylamine, 1,3,5-triphenyl 2 pyrazoline, bis(4- diethylamino)-l,l,1-triphenylethane, 4,4 bis(diethy1- amino)-2,2'-dimethyltriphenylmethane, bis(4 diethylamino)tetraphenylmethane
  • a photoconductive element for use in electrophotography comprising a support having coated thereon a photoconductive Composition comprising:
  • a photoconductive element for use in electrophotography comprising a support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a support having coated thereon a photoconductive composition comprising:
  • 'A photoconductive element for use ine'lectrophotogfra'phy comprising a support having coated thereon a ph'oto'conductive' composition
  • a ph'oto'conductive' composition comprising: I (a) about 10 to 60% by weight based on'said photoconductive composition of an organic photocon- 'd'ucto'r, (b) a film-forming polymeric binder for the said photoconductor, and 1 12 (c) 0.005 to'5% of' tropylium' perchlorate 'as 'asensi tizer for the said photoconductor.

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  • Photoreceptors In Electrophotography (AREA)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3647432A (en) * 1969-10-22 1972-03-07 Colin Holstead Carbazolylmethane dye salts as sensitizers for photoconductor compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5764596A (en) * 1980-10-06 1982-04-19 Fuji Photo Film Co Ltd Heat mode recording material
FR2603713B1 (fr) * 1986-09-10 1992-07-24 Canon Kk Derive nouveau de 5h-dibenzo(a,d)cycloheptane-(ene)ylidene, son procede de production et support electrophotographique photosensible le contenant
JP2858167B2 (ja) * 1989-11-16 1999-02-17 コニカ株式会社 電子写真感光体

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3141770A (en) * 1961-10-23 1964-07-21 Eastman Kodak Co Electrophotographic layers and sensitizers for same
US3143544A (en) * 1958-10-24 1964-08-04 Gevaert Photo Prod Nv Triarylphosphonium cyclopentadienylide methine dyes and photographic emulsions sensitized therewith

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3143544A (en) * 1958-10-24 1964-08-04 Gevaert Photo Prod Nv Triarylphosphonium cyclopentadienylide methine dyes and photographic emulsions sensitized therewith
US3141770A (en) * 1961-10-23 1964-07-21 Eastman Kodak Co Electrophotographic layers and sensitizers for same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3647432A (en) * 1969-10-22 1972-03-07 Colin Holstead Carbazolylmethane dye salts as sensitizers for photoconductor compositions

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BE708638A (ru) 1968-06-28
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