USRE29554E - Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers - Google Patents

Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers Download PDF

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Publication number
USRE29554E
USRE29554E US05/672,702 US67270276A USRE29554E US RE29554 E USRE29554 E US RE29554E US 67270276 A US67270276 A US 67270276A US RE29554 E USRE29554 E US RE29554E
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US
United States
Prior art keywords
dicyanomethylene
sensitizer
moles
photoelectrostatic member
photoelectrostatic
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 - Lifetime
Application number
US05/672,702
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English (en)
Inventor
Evan S. Baltazzi
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.)
AB Dick Co
Original Assignee
Multigraphics Inc
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Filing date
Publication date
Application filed by Multigraphics Inc filed Critical Multigraphics Inc
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Publication of USRE29554E publication Critical patent/USRE29554E/en
Anticipated expiration legal-status Critical
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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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0603—Acyclic or carbocyclic compounds containing halogens
    • 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

Definitions

  • This invention relates generally to organic photoconductive members of the donor-acceptor type, and in particular, relates to the addition of ⁇ -acid-type acceptors for the purpose of increasing the sensitivity range to electromagnetic radiation in the visible portion of the spectrum.
  • Suitable donor materials may be organic photoconductive polymers containing aromatic or heterocyclic nuclei.
  • Typical of such systems in the prior art is the photoconductive material formed by applying polymerized N-vinylcarbazole (P.V.K.) onto a suitable substrate.
  • Organic photoconductors in general, and the polyvinylcarbazole polymer in particular, have a rather slow response to electromagnetic radiation in the visible range being more sensitive to radiation in the ultraviolet region of the spectrum.
  • the broadening of the spectral response of the organic photoconductive donor to include the visible range of the spectrum may be accomplished by the addition of certain additives known as ⁇ -acids.
  • polyvinylcarbazole as the typical photoconductive donor, however, it is to be understood that the acceptors or sensitizers may be used with other polymeric organic photoconductive donors such as: polystyrenes, polyvinylxylenes, poly-vinylnaphthalene, poly-2-vinylnaphthalene, poly-4-vinylbiphenyl, poly-9-vinylanthracene, poly-3-vinylpyrene, poly-2-vinylquinoline, and polyacenapthalene.
  • polystyrenes polystyrenes, polyvinylxylenes, poly-vinylnaphthalene, poly-2-vinylnaphthalene, poly-4-vinylbiphenyl, poly-9-vinylanthracene, poly-3-vinylpyrene, poly-2-vinylquinoline, and polyacenapthalene.
  • Photoconductive monomeric materials may be used such as: aromatic hydrocarbons: naphthalene, anthracene, benzanthrene, chrysene, p-diphenylbenzene, diphenyl anthracene, triphenylene, p-quaterphenyl, sexiphenyl; heterocycles such as N-alkyl carbazole, thiodiphenylamine, oxadiazoles, e.g.
  • 2,5-bis-(p-aminophenyl)-1,3,4-oxadiazole triazoles such as 2,5-bis-(p-aminophenyl)-1,3,4-triazole
  • N-aryl-pyrazolines such as 1,3,5-triphenyl-pyrazoline
  • hydro imidazoles such as 1,3-diphenyltetrahydroimidazole
  • oxazole derivatives such as 2,5-diphenyloxazole-2 -p-dimethylamino-4,5-diphenyloxazole
  • thiazole derivatives such as 2-p-dialkylaminophenyl-methyl-benzothiazole.
  • the polymeric material such as poly-N-vinylcarbazole is dissolved in a suitable solvent such as chlorobenzene.
  • a suitable solvent such as chlorobenzene.
  • the polymer is available under the tradename Luvican sold by Badische Anilin- und Sodafabrik A.G., Ludwigshafen, Germany.
  • the molecular weight of the polymer can vary over a wide range, such as from 20,000-5,000,000.
  • the preferred molecular weight range for the poly-N-vinylcarbazole is from 200,000 to 2,000,000.
  • a sensitizing material coming within the above general formula in an amount which is expressed in moles of sensitizer per 100 moles of the organic polymer.
  • the molecular weight is taken on the basis of the molecular weight of the vinylcarbazole monomer.
  • the range is from 0.1 mole to about 100 moles of sensitizer per 100 moles of organic polymer based on the molecular weight of the monomer.
  • the preferred range is from 1 mole to about 35 moles of sensitizer per 100 moles of organic photoconductor. It will be understood that the mole relationship when using an organic photoconductive polymer is based on the weight of the monomer as for example P.V.K. is considered to have a molecular weight of the vinylcarbazole monomer or 193.1. Further, it will be appreciated that the sensitizers of the instant invention can be used with both organic polymeric materials or monomeric organic photoconductive materials.
  • the fluorenylidene malonodinitrile or the fluorenylidene derivatives of substituted malonodintriles when combined with the photoconductive material forms a donor-acceptor complex.
  • the improved photoresponse of the system depends on the solubility of the complex in the solvent system that is employed. A wide range of solvents and solvent blends may be used depending on the particular polymer or monomeric material with which the sensitizer combines.
  • solvents are presented below as exemplary of suitable materials but it is not intended to limit the invention to this group; acetone, acetyl acetone, acetyl chloride, amyl acetate, amyl formate, benzaldehyde, butyl acetate, butyl bromide, butyl methacrylate, butyl Cellosolve, butyl stearate, butyrolactone, Cellosolve, cyclohexanone, diacetone alcohol, butyl ether, diethyl ether, dimethylether, dioxane-1,4, ethylbenzoate, ethyl chloride, ethylene oxide, furan, hexanediol, methyl Cellosolve, propyl acetate, propyl benzone, tetrahydrofuran.
  • the preferred solvents are tetrahydrofuran, dioxane-1,4 and cyclohexanone.
  • the dicyanomethylene fluorenes or dicyanomethylene substituted fluorenes is dissolved in a solvent such as tetrahydrofuran, dioxane-1,4 or cyclohexanone. It may be desirable to combine two or three solvents in the circumstance that is is desired to control the evaporation rate after the solution is cast on the base support during the drying process the manner of combining the ingredients into the solvent or solvent blend is not critical. To the solvent may be added both the sensitizer and the photoconductor or they may be dissolved separately in split mixtures and then combined.
  • Suitable resin materials generally used for this purpose are well known.
  • binders one may use chorinated rubbers, styrene-butadiene, silicone resins and polyvinylformal.
  • the preferred sensitizers are the nitro-substituted dicyanomethylene fluorenes but the other substituents yield derivatives which are excellent sensitizers.
  • polyvinylcarbazole and the sensitizer there may be added additional chlorobenzene in order to adjust the viscosity of the coating solution to the proper viscosity level.
  • the viscosity level will depend on the type of coating equipment used.
  • a thin film of the coating solution is uniformly applied to the conductive substrate.
  • the solvent is then evaporated by forced air drying.
  • the coating solution is applied at a rate such that the dry sheet has a photoconductive layer in the range of 0.15-0.50 mil, the preferred thickness being in the range of 0.2-0.3 mil thickness.
  • the photoelectrostatic member of Example I when exposed to electromagnetic radiation in the visible range, such as a Sylvania filament lamp in a quartz envelope, produced a measured rate voltage drop of 55.5 volts per foot-candle-second from a saturation voltage level of about 800 volts to a voltage level of 300 volts.
  • the voltage drop in volts per foot-candle-second from a saturation voltage of 800 volts was 0.13 volt per foot-candle-second down to the same level of 300 volts.
  • the photoelectrostatic members prepared using the other sensitizers gave similar increased photoresponse when added to the polyvinylcarbazole material.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US05/672,702 1969-06-05 1976-04-01 Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers Expired - Lifetime USRE29554E (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83087969A 1969-06-05 1969-06-05
NL7013324A NL7013324A (en, 2012) 1969-06-05 1970-09-09

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
US67924667A Continuation-In-Part 1967-10-30 1967-10-30
US83087969A Reissue 1967-10-30 1969-06-05

Publications (1)

Publication Number Publication Date
USRE29554E true USRE29554E (en) 1978-02-28

Family

ID=26644576

Family Applications (1)

Application Number Title Priority Date Filing Date
US05/672,702 Expired - Lifetime USRE29554E (en) 1969-06-05 1976-04-01 Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers

Country Status (4)

Country Link
US (1) USRE29554E (en, 2012)
DE (1) DE1954252B2 (en, 2012)
GB (1) GB1301295A (en, 2012)
NL (1) NL7013324A (en, 2012)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5153085A (en) * 1988-10-05 1992-10-06 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD114874A1 (en, 2012) * 1974-05-16 1975-08-20
EP0615165A3 (en) * 1993-03-12 1995-08-02 Konishiroku Photo Ind Electrophotographic photoreceptor.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159483A (en) * 1959-07-14 1964-12-01 Azoplate Corp Process for the preparation of electrophotographic reversed images
US3232755A (en) * 1959-07-01 1966-02-01 Azoplate Corp Photoconductive layers for electrophotographic purposes
US3257207A (en) * 1963-08-30 1966-06-21 Polaroid Corp Photographic products, processes and compositions
US3287119A (en) * 1961-07-24 1966-11-22 Azoplate Corp Process for the sensitization of photoconductors
US3408190A (en) * 1966-03-15 1968-10-29 Xerox Corp Electrophotographic plate and process employing photoconductive charge transfer complexes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232755A (en) * 1959-07-01 1966-02-01 Azoplate Corp Photoconductive layers for electrophotographic purposes
US3159483A (en) * 1959-07-14 1964-12-01 Azoplate Corp Process for the preparation of electrophotographic reversed images
US3287119A (en) * 1961-07-24 1966-11-22 Azoplate Corp Process for the sensitization of photoconductors
US3257207A (en) * 1963-08-30 1966-06-21 Polaroid Corp Photographic products, processes and compositions
US3408190A (en) * 1966-03-15 1968-10-29 Xerox Corp Electrophotographic plate and process employing photoconductive charge transfer complexes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5153085A (en) * 1988-10-05 1992-10-06 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process

Also Published As

Publication number Publication date
NL7013324A (en, 2012) 1972-03-13
DE1954252A1 (de) 1970-12-10
DE1954252B2 (de) 1979-08-23
GB1301295A (en, 2012) 1972-12-29

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