US3533785A - Photoconductive compositions and elements - Google Patents

Photoconductive compositions and elements Download PDF

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US3533785A
US3533785A US630144A US3533785DA US3533785A US 3533785 A US3533785 A US 3533785A US 630144 A US630144 A US 630144A US 3533785D A US3533785D A US 3533785DA US 3533785 A US3533785 A US 3533785A
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phthalimide
photoconductive
mole
percent
compound
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Charles J Fox
Arthur L Johnson
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03G5/09—Sensitisors or activators, e.g. dyestuffs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/48—Isomerisation; Cyclisation
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority

Definitions

  • This invention relates to electrophotography.
  • it relates to organic photoconductor-containing compositions and elements having enhanced photosensitivity when electrically charged, and to a method of preparing organic compounds which are photoconductors.
  • 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 selected to be deposited on the exposed surface in accordance with either the charge pattern or the absence of charge pattern as desired.
  • the deposited marking material can 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 can similarly be fixed.
  • the electrostatic latent image can be transferred to a second element and developed there.
  • Q and Q are each substituted or unsubstituted phenyl radicals such as phenyl, aminophenyl, tolyl, halophenyl, etc., or when taken together comprise the atoms required to complete an imide ring system having 5 or 6 atoms in its nucleus which can optionally be fused to one or more substituted or unsubstituted carbocyclic ring sys tems or can be an integral part of an addition copolymer chain such as imide-styrene copolymers, imide-olefin copolymers, imide-vinyl chloride copolymers, imide-acrylonitrile copolymers, etc., and R is (1) A substituted or unsubstituted phenyl radical such as described above for Q and Q.
  • a heterocyclic radical having 5 or 6 atoms in its heteronucleus including such hetero atoms as oxygen, nitrogen, sulfur and selenium such as quinolyl, benzothi- 3 azolyl, phthalimido, morpholino, pyrimidyl, pyridinyl, pyrazinyl, etc.
  • n can be an integer from 12 preferably an integer from 0-3 and R and R are each a hydrogen atom, an alkyl radical typically having 1-20 carbon atoms such as methyl, ethyl, propyl, hexyl, octyl, nonyl, dodecyl, etc., an aryl radical such as phenyl, naphthyl, tolyl, aminophenyl, alkoxyphenyl, halophenyl, etc., or when taken together with the nitrogen atom of the R substituent comprise the atoms necessary to complete a heterocyclic ring system having or 6 atoms in its heteronucleus which can optionally be substituted or fused at the 2- and 3-positions to a benzenoid ring system,
  • n is an integer from 0-12, preferably an integer from 0-3 and Z and Z are each substituted or unsubstituted phenyl groups or when taken together with their adjacent groups can comprise the atoms required to complete an imide ring system having 5 or 6 atoms in its nucleus which can optionally be fused to one or more substituted or unsubstituted carbocyclic ring systems,
  • Suitable photoconductive imides of the invention within the foregoing class are included in Table I.
  • the compound number assigned is used herein in later examples to identify the named compounds. This list is exemplary only and is not presented as being limiting with respect to the scope of the invention.
  • a preferred class of compounds within the scope of Formula I which are useful in the practice of the present invention are the phthalimides; i.e., those compounds where in Formula I Q and Q form a phthalimide ring system with the adjacent groups.
  • phthalimides are those having the structural formula:
  • R is a lower alkyl radical such as those shown above for R and R and R and R are each hydrogen atoms or dialkylamino or diarylamino radicals.
  • the imides used in the practice of this invention can be prepared by Well-known methods. Typically, a suitable group containing a reactive nitrogen is converted into a primary amine, which is then condensed with an appropriate anhydride to form the corresponding imide. Representative examples illustrating this method of preparation are included in Examples 1 through 14 hereinafter.
  • the copolymer can be prepared by this same procedure. In such cases, a copolymer containing the appropriate anhydride is condensed with the desired primary amine to yield the corresponding imide as an integral portion of the copolymer. Examples 6 and 7 hereinafter further illustrate this method of preparation.
  • the imides corresponding to Formula I wherein R represents the radical are advantageously prepared by a novel procedure.
  • an alkali metal salt of the imide is condensed with an acetal to give the imidoacetal, which is hydrolyzed to the aldehyde.
  • the imidoaldehyde then condenses readily with a secondary amine to give an unsaturated N-substituted imide which can be reduced to the corresponding fully saturated imide photoconductor.
  • This method of preparation is illustrated schematically in Equation 1.
  • R represents a lower alkyl group
  • M represents an alkali metal
  • X represents a halogen
  • y represents an integer from 0-11.
  • the imide is present as an alkali metal salt, preferably a potassium salt, and the acetal is present as a haloacetal, preferably a bromoacetal.
  • the reaction is performed in a solvent such as N,N-dimethylformarnide.
  • the temperature and pressure at which the reaction is carried out can vary over a wide range. The reaction will proceed satisfactorily at room temperature (20 C.) and atmospheric pressure. Elevated temperatures and reflux are preferred, however, since under such conditions the reaction proceeds more rapidly. The upper temperature is generally limited by the boiling point of the solvent; higher boiling solvents permitting higher temperatures of reaction.,Ternperatures of from 50 C. to 150 C. are typical of suitable elevated temperatures.
  • the reaction is normally performed at atmospheric pressure, either elevated or reduced pressures. can be employed if desired.
  • Hydrolysis of the imidoacetal to the imidoaldehyde is generally effected with formic acid in the presence of a mineral acid such as hydrochloric acid.
  • the reaction will proceed satisfactorily under ambient conditions (room temperature and atmospheric pressure). Elevated temperatures up to C. are preferred for this reaction.
  • Condensation of the imidoaldehyde with a secondary amine is performed in an organic solvent such as benzene, toluene, etc.
  • the temperature and pressure can vary over a wide range. As in the case of the condensation to the imidoacetal, this reaction will proceed at room temperature and atmospheric pressure. Elevated temperatures are preferred, the upper temperature limit being controlled generally by the boiling point of the solvent. Temperatures up to C. are typical of suitable temperatures for this reaction. Reduced or elevated pressures can be employed.
  • the unsaturated imide can be converted to the saturated N-substituted imide by standard hydrogenation procedures.
  • the unsaturated N-substituted imide can be contacted with hydrogen at elevated temperature and pressure in the presence of a catalyst such as carbonized platinum or finely divided platinum or nickel.
  • This novel method of preparing certain of the N-substituted imides of this invention yields a novel class of compounds which could not be easily obtained by prior art processes, These compounds are the unsaturated N- substituted imides generally represented by structural Formula IV in Equation I above. As compounds of this formula are photoconductors per so they can be incorporated in suitable coating compositions for use in the practice of this invention. The unsaturated imides also find use as intermediates in the preparation of the fully saturated imide photoconductors, being reduced to compounds of Formula V as indicated in Equation I.
  • n is an integer from 0 to 12, preferably an integer from 0 to 3
  • T is a substituted or unsubstituted phenylene or naphthylene radical
  • R is a lower alkyl radical as defined above
  • X is a hydrogen atom or a halogen atom, preferably a bromine atom
  • T is a substituted or unsubstituted phenylene or naphthylene radical
  • R is as defined above, and R is a dialkylamino radical, diarylamino radical, keto radical, alkoxy radical, alkyl radical, or halogen atom.
  • the photoconductive composition can be formulated and coated with or without a binder.
  • a binder employed, the compound is dissolved in a solution of binder and solvent and then, after thorough mixing, the composition is coated on an electrically conducting support in a well-known manner, such as swirling, spraying, doctor-blade coating, and the like.
  • Preferred binders for use in preparing the 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; styrenealkyd resins; silicone-alkyd resins; soya-alkyd resins; poly(vinyl chloride); poly(vinylidene chloride); vinylidene chloride acrylonitrile copolymers; poly(vinyl acetals) such as poly(vinyl butyral); polyacrylic and methacrylic esters, such as poly(methylmethacrylate), poly(n-butylmethacrylate), poly(isobutyl methacrylate), and the like; polystyrene; nitrated polystyrene; polymethylstyrene; isobutylene polymers; polyesters, such as poly- (alkylene terephthalates); phenol-formalde
  • styrene-alkyd resins can be prepared according to the method described in U.S. Pats. 2,361,019 and 2,258,423.
  • Suitable resins of the type contemplated for use in the preparation of photoconductive layers are sold under such trade names as Vitel PE-lOl, Cymac, Piccopale 100, Lexan and Saran F220.
  • Other types of binders which can be used in the photoconductive layers of the invention include such materials as parafiin, mineral waxes, and the like.
  • Solvents useful for preparing coating compositions with the compounds of the present invention can include a wide variety of organic solvents for the components of the coating composition.
  • organic solvents for the components of the coating composition.
  • benzene; toluene; acetone; 2-butanone; chlorinated hydrocarbons such as methylene chloride; ethylene chloride; and the like; ethers such as tetrahydrofuran and the like, or mixtures of such solvents can advantageously be employed in the practice of this invention.
  • the photoconductive 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 photoconductive material present can be widely varied in accordance with usual practice. In those cases where a binder is employed, it is normally required that the photoconductive material be present in an amount from about 1 weight percent of the coating composition to about 99 weight percent of the coating composition.
  • a preferrred weight range for the photoconductive material in the coating composition is from about 10 weight percent to about 60 weight percent.
  • Coating thicknesses of the photoconductive composition on a support can vary widely. Normally, a wet coating thickness in the range of about 0.001 inch to about 0.01 inch is useful in the practice of the invention. A preferred range of coating thickness is from about 0.002 inch to about 0.006 inch before drying although such thickness can vary widely depending on the particular application desired for the electrophotographic element.
  • Suitable supporting materials for coating the photoconductive layers of the present invention can include any of the 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 aluminum and the like.
  • An especially useful conducting support can be prepared by coating a support material such as poly (ethylene terephthalate) with a layer containing a semiconductor dispersed in a resin.
  • a suitably conducting coating can be prepared from the sodium salt of a carboxyester lactone of maleic anhydride and a vinyl acetate polymer.
  • the photoconductive layers of the invention can also be sensitized by the addition of effective amounts of sensitizing compounds to exhibit improved electrophotosensitivity.
  • Sensitizing compounds useful with the photoconductive compounds of the present invention can be selected from a wide variety of materials including such materials as pyrylium, thiapyrylium, and selenapyrylium dye salts disclosed in Van Allan et al. U.S. Pat.
  • fiuorenes such as 7,12-di0xo 13 dibenzo(a,h)fiuorene, 5,10-dioxo-4a,l1-diazabenzo(b)fluorene, 3,13-dioxo-7-ox adibenzo(b,g)fluorene, and the like; aromatic nitro compounds of the kinds described in U.S. Pat. 2,610,120; anthrones like those disclosed in U.S. Pat. 2,670,285; quinones, U.S. Pat. 2,670,286; benzophenones U.S. Pat. 2,670,287; thiazoles U.S. Pat. 2,732,301; mineral acids; carboxylic acids, such as maleic acid, dichloroacetic acid,
  • sensitizers preferred for use with the compounds of this invention are selected from pyrylium and thiapyrylium salts, fiuorenes, carboxylic acids and triphenylmethane dyes.
  • sensitizing compound is employed with the compounds of the invention to form a sensitized electrophotographic element
  • Other methods of incorporating the sensitizer or the effect of the sensitizer can, however, be employed consistent with the practice of this invention.
  • no sensitizing compound is required to give photoconductivity in the layers which contain the photoconducting substances of this invention, therefore, no sensitizer is required in a particular photoconductive layer.
  • relatively minor amounts of sensitizing compound give substantial improvement in speed in such layers, the sensitizer is preferred.
  • 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.
  • substantial 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.
  • a sensitizer is added to the coating composition in an amount by weight from about 0.005 to about 5.0 percent by weight of the total coating composition.
  • composition of the present invention can be employed in photoconductive elements useful in any of the well-known electrophotographic processes which require photoconductive layers.
  • One such process is the xerographic process.
  • an electrophotographic element held in the dark is given a blanket electrostatic charge by placing it under a corona discharge to give a uniform charge to the surface of the photoconductive layer. This charge is retained by the layer owing to the substantial dark 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 photoconductive layer is then selectively dissipated from the surface of the layer by imagewise exposure to light by means of a conventional exposure operation such as, for example, by a contact-printing technique, or by lens projection of an image, or reflex or birefiex techniques and the like, to thereby form a latent electrostatic image in the photoconductive layer.
  • Exposing the surface in this manner forms a pattern of electrostatic charge by virtue of the fact that light energy striking the photoconductor causes the electrostatic charge in the light struck areas to be conducted away from the surface in proportion to the intensity of the illumination in a particular area.
  • the charge pattern produced by exposure is then developed or transferred to another surface and developed there, i.e., either the charged or uncharged areas rendered visible, by treatment with a medium comprising electrostatically responsive particles having optical density.
  • the developing electrostatically responsive particles can be in the form of a dust or powder and generally comprise a pigment in a resinous carrier called a toner.
  • a preferred method of applying such a toner to a latent electrostatic image for solid area development is by the use of a mag netic brush. Methods of forming and using a magnetic brush toner applicator are described in the following U.S. Pats: 2,786,439; 2,786,440; 2,786,441; 2,811,465; 2,874,- 063; 2,984,163; 3,040,704; 3,117,884; and Reissue 25,-
  • Liquid development of thelatent electrostatic image can also be used.
  • the developing particles are carried to the image-bearing surface in an electrically insulating liquid carrier.
  • Methods of development of this type are widely known and have been described in the patent literature, for example, US. Pat. 2,296,691 and in Australian Pat. 212,315.
  • dry developing processes the most widely used method of obtaining a permanent record is achieved by selecting a developing particle which has as one of its components a low-melting resin. Heating the powder image then causes the resin to melt or fuse into or on the element. The powder is, therefore, caused to adhere permanently to the surface of the photoconductive layer.
  • a transfer of the charge image or powder image formed on the photoconductive layer can be made to'a second support such as paper which would then become the final print after developing and fusing or fusing respectively.
  • Techniques of the types indicated are well known in the art and have been described in a number of US. and foreign patents, such as US. Pats. 2,297,691 and 2,551,582 and in RCA Review, vol. 15 (1954) pages 469-484.
  • the compositions of the present invention can be used in electrophotographic elements having many structural variations.
  • the photoconductive composition can be coated in the form of single layers or multiple layers on a suitable opaque or transparent conducting support.
  • the layers can be contiguous or spaced having layers of insulating material or other photoconducting material between layers or overcoated or interposed between the photoconducting layer or sensitizing layer and the conducting layer. It is also possible to adjust the position of the support and the conducting layer placing a photoconductor layer over a support and coating the exposed face of the support or the exposed or overcoated face of the photoconductor with a conducting layer. Configurations differing from those contained in the examples can be useful or even preferred for the same or different applications for the electrophotographic element.
  • EXAMPLE 7 Preparation of a copolymer of ethylene and N-[2-(1,2,3,4- tetrahydro-Z-methyl- 1 -quinolyl) ethyl] maleimide (Compound 3 1)
  • the title compound was prepared by the procedure described in the preceding example from a 1:1 ethylene: maleic anhydride copolymer (DX 840-11 sold by Monsanto Chemical Co.) and N-(2-aminoethyl)-l,2,3,4-tetrahydroquinaldine. Yield: 8.3 g.
  • N-(p-diphenylaminophenyl)phthalimide (Compound 34) A mixture of 35.1 g. (0.2 mole) of diphenylamine, 49.8 g. (0.2 mole) of 1-iodo-4-nitrobenzene, 27.6 g. (0.2 mole) of anhydrous potassium carbonate, 1 g. of copper powder, and 200 ml. of nitrobenzene was heated under reflux for 24 hours. The nitrobenzene was then removed by steam distillation and the residue was washed with water, dissolved in 400 ml. of benzene, and filtered. Removal of the benzene afforded a dark residue which was distilled at 170 210 C./ 101.4. There was obtained 17.2 g. of yellow-orange pnitrotriphenylarnine following recrystallization from absolute alcohol. M.P. 144.5- 146 C.
  • EXAMPLE 17 The following compounds were prepared in the manner of Example 15 from phthalimidoacetaldehyde and the appropriate secondary amine:
  • EXAMPLE 18 Solutions each containing one of the photoconducting imides designated Compounds 1 thru 49, 53, and 54 were made for coating on a support material by mixing 0. 15 part of the imide with 0.002 part of Sensitizer A and dissolving these together with 0.5 part by weight of a resinous polyester binder with suitable stirring in dichloromethane The resultant mixtures were then each handcoated on an aluminum-laminated paper support.
  • the polyester used is a copolymer of terephthalic acid and a glycol mixture comprising a 9:1 wt. ratio of 2,2-bis[4- ('fl-hydroxyethoxy)phenyl]propane and ethylene glycol.
  • the wet coating thickness on the support was 0.004 inch.
  • each electrophotographic element was employed in a standard xerographic process which included charging under a positive corona and exposure from behind a positive-appearing line transparency to a 3000 K. tungsten source of ZO-foot-candle illuminance at the exposure surface.
  • the coated surface of the element was dusted with an electrostatically attractable powder having optical density according to the method and materials described in US. Pat. 2,297,691. Images were obtained in every case.
  • EXAMPLE 19 Elements prepared according to Example 18 containing photoconductors as tabulated herein and containing Sensitizer A and a control element containing photoconductor and binder alone were tested by the following procedure. Each element was charged under positive corona source until the surface potential, as measured by an electrometer probe, reached 600 volts. The elements were then individually exposed to a light source in the manner of Example 18, with the exception that the positive transparency was replaced by a stepped density gray scale. The actual positive electrical H and D speeds of each element was determined in the following manner. Each element was electrostatically charged under a corona source until the surface potential, as measured by an electrometer probe, reached about 600 volts. The charged element was then exposed to a light source through a transparent stepped density gray scale.
  • the exposure caused 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 depended on the actual amount of exposure in meter-candle-seconds received by the area.
  • V initial potential
  • V some lower potential
  • the results of these measurements were then plotted on a graph of surface potential V vs. log exposure for each step.
  • the actual positive speed of the element can then be expressed in terms of the reciprocal of the exposure required to reduce the surface potential to any arbitrarily selected value. In Table 2, the actual positive speed is the numerical expression of 10 divided by the exposure in metercandle-seconds required to reduce the 600-volt charged surface potential by 100 volts.
  • Example 25 The procedure and sensitizer of Example 25 were used, with the exception that the polarity of initial charging was negative. The results are presented in Table 9.
  • a photoconductive composition for use in electrophotographic image-forming processes comprising a sensitizing compound and a photoconductor which is an N- substituted imide having the structural formula:
  • Q and Q are each selected from the group consisting of phenyl radicals and, when taken together with the adjacent groups, the atoms necessary to complete an imide ring system having to 6 atoms in its nucleus, and,
  • R is selected from the group consisting of (1) phenyl radicals, (2) heterocyclic radicals, (3) radicals having the structural formula:
  • R and R are each selected from the group consisting of hydrogen atoms, alkyl radicals, aryl radicals, and, when taken together with the nitrogen atom of said R radical, the atoms necessary to complete a heterocyclic ring system having 5 to 6 atoms in its nucleus, (4) radicals having the structural formula:
  • n is an integer from 0 through 12
  • Z and Z are each selected from the group consisting of phenyl radicals and, when taken together with the adjacent groups, the atoms necessary to complete an imide ring system having 5 to 6 atoms in its nucleus
  • a photoconductive composition comprising a sensitizing compound and a photoconductor which is an N- substituted imide having the structural formula:
  • R1 at N Re (I where R is a lower alkyl radical, and R and R are each selected from the group consisting of hydrogen atoms and dialkylamino and diarylamino radicals.
  • the photoconductive composition as defined in claim 1 wherein the sensitizing compound is selected from the group consisting of pyrylium and thiapyrylium sensitizing compounds.
  • the photoconductive composition as defined in claim 1 wherein the sensitizing compound is selected from the group consisting of 2,6-bis(ethylphenyl)-4-(4-n-amyloxyphenyl) thiapyrylium perchlorate, 2,4-bis(4-ethoxyphenyl)-6-(4-n-amyloxystyryl) pyrylium fluoroborate, 2,4- bis(4 ethylphenyl)-6-(4-styrylstyry1)pyrylium perchlorate, 2,4,7-trinitrofluorenone, Crystal Violet, and Rhodamine B.
  • An electrophotographic element comprising a conducting support and a photoconductive layer of a composition comprising an N-substituted imide having the structural formula:
  • Q and Q are each selected from the group consisting of phenyl radicals and, when taken together with the adjacent groups, the atoms necessary to complete an imide ring system having 5 to 6 atoms in its nucleus, and
  • R is selected from the group consisting of (l) phenyl radicals, (2) heterocyclic radicals, (3) radicals having the structural formula:
  • R and R are each selected from the group consisting of hydrogen atoms, alkyl radicals, aryl radicals, and, when taken together with the nitrogen atom of said R radical, the atoms necessary to complete a heterocyclic ring system having to 6 atoms in its nucleus, (4) radicals having the structural formula:
  • n is an integer from 0 through 12
  • Z and Z are each selected from the group consisting of phenyl radicals and, when taken together with the adjacent groups, the atoms necessary to complete an imide ring system having 5 to 6 members in its nucleus,
  • An electrophotographic element comprising a conducting support having coated thereon a layer of a photoconductive composition comprising a sensitizing compound and an N-substituted imide selected from the group consisting of compounds having the structural formula:
  • R and R are each selected from the group consisting of hydrogen atoms and lower alkyl radicals, and compounds having the structural formula:
  • R is a lower alkyl radical
  • R and R are each selected from the group consisting of hydrogen atoms and dialkylamino and diarylamino radicals.
  • a photoconductive element as defined in claim 10 wherein the sensitizing compound is selected from the group consisting of pyrylium and thiapyrylium sensitizing compounds.
  • a photoconductive element as defined in claim 10 wherein the sensitizing compound is selected from the group consisting of 2,6bis(ethylphenyl)-4-(4-n-arnyloxyphenyl)thiapyryliurn perchlorate, 2,4 bis(4 ethoxyphenyl)-6- (4-n-amyloxystyryl)pyrylium fiuoroborate, 2,4- bis(4-ethylphenyl)-6-(4-styrylstyryl) pyrylium perchlorate, 2,4,7-trinitrofluorenone, Crystal Violet, and Rhodamine B.
  • a photoconductive element comprising a conductive support having coated thereon a layer of a photoconductive composition comprising N-[2-l,2,3,4-tetrahydro 2-methyl 1 quinolyl)ethyl]phthalimide as a photoconductor sensitized with 2,4-bis(4-ethylphenyl)-6-(4-styrylstyry1)pyrylium perchlorate.

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787207A (en) * 1971-12-16 1974-01-22 Matsushita Electric Ind Co Ltd Electrophotographic photosensitive plate having a polyimide intermediate layer
US4124593A (en) * 1975-11-13 1978-11-07 Ciba-Geigy Corporation Aromatic dicarboximides
US4355089A (en) * 1977-08-09 1982-10-19 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Ten Behoeve Van Nijverheid, Handel En Verkeer Process for producing a photoconductive polyimide coating upon a substrate
US5139909A (en) * 1990-07-31 1992-08-18 Xerox Corporation Perinone photoconductive imaging members

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69022724T2 (de) * 1990-06-19 1996-05-02 Agfa Gevaert Nv Elektrophotographisches Aufzeichnungsmaterial.
JP4423433B2 (ja) * 1999-10-07 2010-03-03 富士電機システムズ株式会社 電子写真用感光体材料を製造する方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2729673A (en) * 1951-11-30 1956-01-03 Du Pont Carboxylation of aromatic compounds
US3250615A (en) * 1961-10-23 1966-05-10 Eastman Kodak Co Light-sensitive layers containing pyrylium and thiapyrylium salts
US3316087A (en) * 1959-10-31 1967-04-25 Azoplate Corp Photoconductor coatings for electrophotography

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2729673A (en) * 1951-11-30 1956-01-03 Du Pont Carboxylation of aromatic compounds
US3316087A (en) * 1959-10-31 1967-04-25 Azoplate Corp Photoconductor coatings for electrophotography
US3250615A (en) * 1961-10-23 1966-05-10 Eastman Kodak Co Light-sensitive layers containing pyrylium and thiapyrylium salts

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787207A (en) * 1971-12-16 1974-01-22 Matsushita Electric Ind Co Ltd Electrophotographic photosensitive plate having a polyimide intermediate layer
US4124593A (en) * 1975-11-13 1978-11-07 Ciba-Geigy Corporation Aromatic dicarboximides
US4355089A (en) * 1977-08-09 1982-10-19 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Ten Behoeve Van Nijverheid, Handel En Verkeer Process for producing a photoconductive polyimide coating upon a substrate
US4363860A (en) * 1977-08-09 1982-12-14 Nederlandsch Organisatie Voor Toegepast-Natuurvetenschappelijk Onderzoek Ten Behoeve Van Nyserheid, Handel En Verkeer Photoconductive polyimide coating upon a substrate
US5139909A (en) * 1990-07-31 1992-08-18 Xerox Corporation Perinone photoconductive imaging members

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