US3658520A - Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups - Google Patents

Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups Download PDF

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Publication number
US3658520A
US3658520A US706780A US3658520DA US3658520A US 3658520 A US3658520 A US 3658520A US 706780 A US706780 A US 706780A US 3658520D A US3658520D A US 3658520DA US 3658520 A US3658520 A US 3658520A
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Prior art keywords
photoconductive
percent
composition
weight based
film
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US706780A
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Thomas B Brantly
Lawrence E Contois
Charles J Fox
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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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen

Definitions

  • ABSTRACT Triarylamines having at least one of the aryl radicals substituted by an active hydrogen-containing group are good organic photoconductors in electrophotographic systems.
  • 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 bycontacting 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 the discharge 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, ortransferred to a second element to which it can be similarly be fixed.
  • the electrostatic latent image can be transferred to a second element and 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.
  • electrophotographic elements having coated thereon organic photoconductive compositions containing a tiarylamine photoconductor wherein at least one of the aryl radicals is substituted by an active hydrogen-containing group and a sensitizer for the photoconductor.
  • Groups which contain active hydrogen are well known in the art, the definitionof this term being set forth in several textbooks such as Advanced Organic Chemistry, R. C. Fuson, pp. 154-157, John Wiley & Sons, 1950.
  • active hydrogen-containing group as used herein includes those compounds encompassed by the discussion in the textbook cited above and in addition include those compounds which contain groups which are hydrolyzable to active hydrogen-containing groups.
  • Typical active hydrogen-containing groups which are sub stituted on an aryl radical of the triarylamine according to this invention include:
  • ester radicals e.g. i10 R wherein R is an alkyl oran aryl group
  • R is an alkyl oran aryl group
  • lower alkylene hydroxy radicals e.g., having one to eight carbon atoms
  • lower alkylene carboxy radicals e.g., having two to eight carbon atoms
  • R is a hydrogen atom, an alkyl group or an aryl group
  • R is a hydrogen atom, an alkyl group or an aryl group
  • D and E are phenyl or lower alkyl radicals.
  • the preferred photoconductors of this invention are represented by the following structure:
  • the organic photoconductors of this invention exhibit substantial improvements in speed over comparable photoconductors which do not have an active hydrogen-containing group (including groups hydrolyzable to active hydrogen-containing groups).
  • those compounds in which Ar and Ar in the above formula are phenyl radicals generally have improved photoconducting properties over those which are substituted by one or two alkyl radicals.
  • p-diphenylaminobenzoic acid generally displays higher electrical speeds than p-diethylaminobenzoic acid of p-N-methyl-N- phenylaminobenzoic acid.
  • Some typical photoconductors of this invention are:
  • Electrophotographic elements of the invention can be prepared with these photoconducting compounds in the usual manner, i.e., by blending a dispersion or solution of a photoconductive compound together with a binder, when necessary or desirable, and coating or forming a self-supporting layer with the photoconductor-containing material. Mixtures of the photoconductors described herein can be employed. Likewise, other photoconductors known in the art can be combined with the present photoconductors. In addition, supplemental materials useful for changing the spectral sensitivity or electrophotosensitivity of the element can be added to the composition of the element when it is desirable to produce the characteristic effect of such materials.
  • the photoconducting compounds of this invention are not sensitive to light unless a sensitizing compound is present. While a wide variety of such substances impart spectral sensitivity to the photoconductors of this invention, it has been found that pyrylium salts, that is the pyrylium, thiapyrylium and selenapyrylium salts of U.S. Pat. No. 3,250,615, are particularly useful for sensitizing these compounds to the extent that they exhibit relatively high electrical speeds compared to those compounds which do not have an active hydrogen-containing group.
  • Other sensitizing compounds useful with the photoconductors of the invention include tluorenes, such as 7.
  • the sensitizing compounds In preparing the photoconducting layers disclosed herein, it is conventional practice to mix a suitable amount of the sensitizing compounds with the 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. In general, 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. Generally, 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.
  • Preferred binders for use in preparing the present photoconductive layers are film-forming polymeric binders 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-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), etc.; polystyrene; nitrated polystyrene; polymethylstyrene;
  • styrene-alkyd resins can be prepared according to the method described in U.S. Pat. Nos. 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-lO l 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, 2-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, 2-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 ofthe 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 ofthe 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 thicknesses 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 thicknesses 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, nickel, or aluminum and the like.
  • Metal (e.g., nickel, etc.) conducting layers deposited by high vacuum deposition techniques can be coated at low coverages so as to be substantially transparent to facilitate image exposure through the support.
  • 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.
  • Suitable conducting layers both with and without insulating barrier layers are described in U.S. Pat. No. 3,245,833.
  • Other suitable conducting layers are described in U.S. Pat. No. 3,120,028.
  • 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. Pat. Nos. 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 uniformchargeto 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 photoconducting layer is then selectively dissipated from the surface of the layer by exposure to light through an 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 charge 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.
  • the developing electrostatically attractable particles can be in the form of a dust, e.g., powder, 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 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, and the expo sure 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 different 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.
  • compositions are handcoated at a wet thickness of 0.004 inch on a conducting layer comprising the sodium salt ofa carboxyester lactone, such as described in U.S. Pat. No. 3,120,028 which in turn is coated on a cellulose acetate film base.
  • the coating blocks are maintained at a temperature of F.
  • These electrophotographic elements are charged under a positive or negative corona source until the surface potentials, as measured by an electrometer probe, reach between about 500 and 600 volts. They are then subjected to exposure from behind a stepped density gray scale to a 3,000 K. tungsten source.
  • the exposure causes reduction of the surface potentials of the elements under each step of the gray scale from their initial potential V,,, to some lower potential V, whose exact value depends on the actual amount of exposure in metencandle-seconds received by the areas.
  • the results of the measurements are plotted on a graph of surface potential V vs. log exposure for each step.
  • the speed is the numerical expression of 10* multiplied by the reciprocal of the exposure in meter-candle-seconds required to reduce the 500 to 600 volt charged surface potentials to l00 volts above 0 volts.
  • Example 3 In order to show the ineffectiveness of sensitizing compounds other than the pyrylium, thiapyrylium and selenapyrylium salts, Example 1 is repeated using the following composition:
  • An electrophotographic element comprising an electrically conductive support having coated thereon a photoconductive composition comprising an electrically insulating polymeric binder, a photoconductor and a sensitizing amount of a pyrylium salt, said photoconductor having the structure:
  • Ar, and Ar are phenyl radicals;
  • Ar is an arylene radical selected from the group consisting of: l. a phenylene radical and 2. a naphthylene radical; and
  • X is an active hydrogen-containing group selected from the group consisting of:
  • An electrophotographic element comprising a conducting support having coated thereon a photoconductive composition comprising a sensitizer which is a pyrylium salt, a polymeric binder and a photoconductor selected from the group consisting of:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • a photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:
  • the photoconductive element of claim 7 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).
  • the photoconductive element of claim 8 wherein the film-forming polymeric binder is poly( vinyl metabromobenzoate-co-vinyl acetate).
  • the photoconductive element of claim 9 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).
  • the photoconductive element of claim 10 wherein the film-forming polymeric binder is poly(vinyl metaboromobenzoate-co-vinyl acetate).
  • the photoconductive element of claim 11 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).
  • the photoconductive element of claim 12 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).

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US706780A 1968-02-20 1968-02-20 Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups Expired - Lifetime US3658520A (en)

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Cited By (222)

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