US3864126A - Organic photoconductor with carboxy group containing fluorene or fluorore - Google Patents

Organic photoconductor with carboxy group containing fluorene or fluorore Download PDF

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Publication number
US3864126A
US3864126A US431730A US43173074A US3864126A US 3864126 A US3864126 A US 3864126A US 431730 A US431730 A US 431730A US 43173074 A US43173074 A US 43173074A US 3864126 A US3864126 A US 3864126A
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United States
Prior art keywords
fluorenone
carboxylic acid
compounds
mol
vinylcarbazole
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Expired - Lifetime
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US431730A
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English (en)
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Katsuhiko Nishide
Tsuyoshi Eida
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Canon Inc
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Canon Inc
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • 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
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • the above drawback may be avoided by adding to the organic photoconductive member electro acceptive compounds which are called rr acid or Lewis acid.
  • electro acceptive compounds which are called rr acid or Lewis acid.
  • the addition of less than lmol% of an electron acceptive compound to an organic photoconductive material provides particularly high photosensitivity for the range of ultraviolet rays.
  • a large amountof electron acceptive compound is added, i.e. 49 to 123 mol% of trinitro fluorenone as the electron acceptive compound is added to poly-9-vinylcarbazole of organic photoconductive material to provide high sensitivity for white light.
  • the electron acceptor compounds as used in such sensitizing methods have strong polar groups, they are generally insoluble in organic solvents or easily crystallized. Thus, the kinds of solvents which can be used, are disadvantageously limited and it is therefore difficult to select arbitarily in preparing a photosensitive layer a suitable solvent for the preparation conditions thereof.
  • the electron acceptor compounds crystallize markedly easily when their solvents vaporize at coating step, it is difficult to form an even photosensitive layer.
  • the electron acceptor compounds are slightly soluble, the amount of the electron acceptor compound to be added, is limited and it often follows that the sensitizing effect of the electron acceptor compound cannot be completely attained in practical usages.
  • the comparativity of the electron acceptor compound with the organic photoconductive material is low, the electron acceptor compound crystallizes on the surface of photosensitive layer after a relatively short storage period, and now they cannot be used.
  • An object of this invention is to provide novel electron acceptor compounds which can be used as a sensitizer in com hination with organic photoconductive matcrials.
  • Another object of this invention is to improve the solubility of electron acceptor compounds in organic solvents so as to increase the amount of the electron acceptor compound to be added and the kinds of solvents to be used.
  • R l COR 2 X i i wherein R R and R are nitro, cyano, halogen, trifluoromethyl, acyl, lower alkyl, lower alkoxy, aryl, aralkyl, or hydrogen; X is oxygen or malononitrile group connected by double bond; R is substituted or nonsubstituted, alkyloxy, alkylamino, aralkyloxy; aralkylamino, aryloxy or arylamino group containing 4 to 30 carbon atoms; and R R and R may be the same or different and furthermore the carbon number of the lower alkyl or lower alkoxy group is preferably 1 to 6 from the standpoint of easy production.
  • the additional advantage which is brought about by using the above compounds, is that there may be reduced or completely removed plasticizers which are added in the preparation of photosensitive layer and which are apt to reduce the sensitivity of the photosensitive layer.
  • the above compounds may be generally prepared from the corresponding 9-fluorenone carboxylic acids and 9-fluorenone carboxylic acid ester or amide derivatives may be prepared according to conventional methods of preparing ester or amide.
  • 9-dicyanomethylene fluorenone carboxylic acid ester and amide derivatives may be prepared by reacting the corresponding 9- fluorenone carboxylic acid with malononitrile and thereafter esterifying or forming amido, or by reacting 9-fluorenone carboxylic acid esteror amido derivatives with malononitrilef
  • the typical methods of preparing the above compounds are givenbelow.
  • fluorenone-4- Organic photoconductive materials as herein used are preferably such as to act as the electron donative member as the above compounds when combined with organic photoconductive materials can act as the electron acceptor member.
  • they include low molucular type organic photoconductive materials such as amyl hydrazone derivatives, oxadiazole derivatives, pyrazoline derivatives, imidazolone derivatives, imidazolinethione derivatives, benzimidazole derivatives, benzoxazole derivatives, and benthiazole deriva tives; polymer containing heterocylic ring such as carbazole ring or polynulclear aromatic rings such as naphthalene ring or anthrathene ring which are disclosed for example in Japanese Pat. Publication Nos. 10966/1959, 812/1961, 18674/1967. 25230/1967 and the like.
  • Representative materials used as an organic photoconductive material in the present invention are as follows:
  • A. Polymer having a carbazole ring such as poly-9- vinylcarbazole, 9-vinylcarbazole copolymer, 3-nitro-9-vinylcarbazole copolymer, 3- methylamino-9-vinylcarbazole copolymer, nitrated poly-9-vinylcarbazole, 3,6-dibromo-9- vinylcarbazole copolymer, poly-9-vinyl-3- aminocarbazole, chlorinated poly-9- vinylcarbazole, thiocyanated poly-9- vinylcarbazole, cyanated poly-9-vinylcarbazole, brominated poly-9-vinylcarbazole, 3-iodo-9- vinylcarbazole copolymer, poly-3,6-diiodo-9- vinylcarbazole, poly-3-benzylideneamino-9- vinylcarbazole, 3,6-dibromo-9-vinylcarbazolc copolymer,
  • Aromatic amino derivatives such as aminopolyphenyl, (allylidene) azines, N-N'-dialkyl-N, N-dibenzylphenylenediamine, N,N,N',N-tetrabenzyl-phenylenediamine, N,N-diphenyl-P- Phenylenediamine, N,N-dinaphtyl-pphenylenediamine, 4,4-dimethylaminophendiphenone.
  • Diphenylmethanes and triphenylmethanes such as diphenylmethane dye dye leuco base and triphenylmethane dye leuco base.
  • Heterocyclic compounds such as oxadiazole, 5- aminothiazole, 4,1,2-triazole, imidazolone, oxazole, imidazole, pyrazoline, imidazoline, polyphenylenethiazole, 1,6-methoxyphenezine, pyrazolinopyrazoline derivatives and the like.
  • Compounds having a condensed ring such as benzothiazole, benzimidazole, and benzoxazole, for example, -tetraphenylhexatriene, 2-(4- diaminophenyl-benzoxazole and 2-(4- dimethylaminophenyl) benzoxazole, aminoacridine, quinoxaline, diphenylenehydrazones, pyrrocoline derivatives, 9,10-dihydroanthraoene derivatives and the like.
  • benzothiazole benzimidazole
  • benzoxazole for example, -tetraphenylhexatriene, 2-(4- diaminophenyl-benzoxazole and 2-(4- dimethylaminophenyl) benzoxazole, aminoacridine, quinoxaline, diphenylenehydrazones, pyrrocoline derivatives, 9,10-dihydroanthraoene derivatives and
  • Condensation products such as condensation products of aldehydes and aromatic amines. reaction product of secondary aromatic amines and aromatic halides. polypyromethane-imidopoly-pphenylene-l ,3,4-oxadiazole and the like.
  • Vinyl polymers except polyvinylcarbazole such as a-alkylacrylic acid, amide polymers polyvinylacridine, poly-[ l ,5-diphenyl-3-(4-vinylphenyl)-2- pyrazoline], poly-(1,5-diphenylpyrazoline), polyacenaphthylene, neuclear substituted polyacenaphthylene, polyvinylanthracene, poly-2-vinyldibenzothiophene and the like.
  • Materials providing good results of sensitizing treatment of this invention among these organic photocon ductive materials are polymers having a carbazole ring and their derivatives, aromatic amino derivatives. diphenylmethane derivatives and triphenylmethane derivatives.
  • the organic photoconductive materials and the compounds of this invention are dissolved in proper solvents.
  • the compounds of this invention may be dissolved in numerous kinds of solvents and thus the most proper solvent may be selected from numerous solvents depending upon an organic photoconductive material to be used.
  • the amount of the compound of this invention varies depending upon the purpose thereof. For example, where it is coated on a substrate such as paper, film, and the like and used as an almost colorless or almost colorless, transparent photosensitive layer, it is added within the ratio of0.01 to 10 mol, preferably 0.1 to 5 mol per mol of organic photoconductive material (if the photoconductive material is a polymer, it is calculated based upon the molecular weight of unit monomer of the polymer). In this case, high photosensitivity for ultraviolet range is provided. If high sensitivity for visible light is also required, it may be achieved by adding dye sensitizers in such an amount not to color strongly thephotosensitive layer.
  • high sensitivity for white light color is needed as in a master photosensitive plate and if coloration of the photosensitive plate is negligible, high ratio of 10 to mol per 100 mol of organic photoconductive mate rial may be used to provide high sensitivity for visible light.
  • the solution containing the photoconductive material and the compounds of this invention may if necessary include binder resins and other additives, which are coated on a substrate or some special cases used in the form of self-substrate.
  • Comparison Example 1 To the solutions prepared by dissolving 2.0g of poly9- vinylcarbazole in 30ml of the following solvents were added 2,4,7-trinitro fluorenone (TNF) of 10 mol% and 100 mol% based of poly-9-vinylcarbazole. The solubility of TNF in the solvents were measured and indicated in Table below. wherein reference symbol 0 means that TNF is soluble and X means that TNF is insoluble.
  • the photosensitive layer was charged, exposed to light, and developed as in Example 1 and there was thus obtained an excellent image.
  • the proper exposure amount was 550 Lux sec.
  • EXAMPLE 3 A solution prepared by dissolving 2g of poly-3- methyl-9-vinylcarbazole and 38mg of 2,7,-dinitro-9- fluoroenone-4-carboxylic acid hexyl ester compound (13) in 35ml of chlorobenzene and a solution prepared by dissolving 11.6mg. of 9,9-diethyl-3,3- dicarbazolyl phenylmethyliodide (sensitizing dye) in 5ml of methylene chloride were mixed to prepare a photosensitive solution.
  • the photosensitive solution was coated on a transparent polyester film on which aluminum was thinly deposited, and dried to form a transparent photosensitive film having a 6p. thick photosensitive layer.
  • the photosensitive layer so prepared was charged, exposed to light and developed as in Example 1 and there was then obtained an excellent copied image. The proper exposure amount was 150 Lux sec.
  • EXAMPLE 4 A solution composed of 2g of poly-9-vinylcarbazole, 4.9g of 4,5,7-trinitro-9 fluorenone-2-carboxylic acid octyl ester compound (10) and 30ml of chlorobenzene was coated on an aluminum plate to form a 10p. thick dry layer.
  • the photosensitive plate so prepared was applied to a rotation type electrometer and after charging negatively at -6KV, exposed to a tungusten lamp (effective illumination intensity, 14.4 Lux Ex- Diameter PVK TNF 4,5,7-trinitro- (mm) (not added) 9-fluorenone-2- carboxylic acid octyl ester 10 mol% 100 mol% 10 mol% 100 mol% 6 O O O O O 5 0 o X o 0 4 X X X 0 0 3 X X X X 0 EXAMPLE 1 posure amount required for decaying the initial poten- A solution composed of 2g of l,3,5- tial 950V to thereof (half-decay exposure) was 4.4
  • triphenylpyrazoline 2g of polyvinyl butyral resin, 70.4mg. of 7-cyano-9-fluroenone-l-carboxylic acid 4- chlorobutyl ester [compound (8)] and 50 ml ofethanol Lux sec.
  • half-decay exposure was 4.0 Lux sec. and where poly- 3,6-chloro-9 -vinylcarbazole was used, the half-decay exposure was 3.6 Lux sec.
  • ratio of said compound to said organic photoconductive material being 001 120 mols to 100 mols.
  • Photosensitive material for electrophotography according to claim 1 in which the compound represented by the formula of claim 1 is added in a ratio of 0.01 to 10 mol per 100 mol of the organicphotoconductive material.
  • Photosensitive plate for electrophotography comprising one or more organic photoconductive materials
  • Photosensitive material for electrophotography comprising one or more organic photoconductive materials and one or more compounds of the formula:
  • R R and R are, the same or different, nitro, cyano, halogen, trifluoromethyl, acyl, lower alkyl, lower alkoxy, aryl, aralkyl, or hydrogen;
  • X is oxygen or malononitrile; and
  • R is, substituted or non-substituted, alkyloxy, alkylamino, aralkyloxy, aralkylamino, aryloxy, or arylamino, containing 4 to 30 carbon atoms, the
  • R R and R are, the same or different, nitro, cyano, halogen, trifluoromethyl, acyl, lower alkyl,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
US431730A 1973-01-10 1974-01-08 Organic photoconductor with carboxy group containing fluorene or fluorore Expired - Lifetime US3864126A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046564A (en) * 1975-07-16 1977-09-06 Xerox Corporation Electrophotographic imaging members with photoconductive layer containing electron acceptor monomers or polymers
US4050934A (en) * 1975-09-22 1977-09-27 Xerox Corporation Electron acceptor monomers and polymers
US4056391A (en) * 1975-09-22 1977-11-01 Xerox Corporation Method for enhancing solid solution stability of electron acceptor molecules and electrophotographic compositions
US4063947A (en) * 1975-10-29 1977-12-20 Xerox Corporation Photoconductive insulating films comprising fluorenone-substituted oligomers
US4105446A (en) * 1975-01-21 1978-08-08 Fuji Xerox Co., Ltd. Organic photoconductive coating compositions containing tricyanovinyl compounds for electrophotography
US4225692A (en) * 1975-09-22 1980-09-30 Xerox Corporation Electron acceptor monomers and polymers
US4584253A (en) * 1984-12-24 1986-04-22 Xerox Corporation Electrophotographic imaging system
US4604295A (en) * 1983-12-22 1986-08-05 Loctite Corporation Visible light absorbing peroxy-esters
US5153085A (en) * 1988-10-05 1992-10-06 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
US6558851B1 (en) * 1999-10-28 2003-05-06 Holo Tech A.S. Optical medium for registration of holographic interferograms
WO2014142844A1 (en) * 2013-03-13 2014-09-18 Hewlett-Packard Development Company, L.P. Organic photoconductors
US9125829B2 (en) 2012-08-17 2015-09-08 Hallstar Innovations Corp. Method of photostabilizing UV absorbers, particularly dibenzyolmethane derivatives, e.g., Avobenzone, with cyano-containing fused tricyclic compounds
US9145383B2 (en) 2012-08-10 2015-09-29 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US9867800B2 (en) 2012-08-10 2018-01-16 Hallstar Innovations Corp. Method of quenching singlet and triplet excited states of pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds have electron withdrawing groups, to reduce generation of reactive oxygen species, particularly singlet oxygen

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287114A (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
US3556785A (en) * 1968-02-23 1971-01-19 Addressograph Multigraph Sensitizers for organic photoconductor comprising orazolone and butenolide derivatives of of fluorenone
US3752668A (en) * 1967-10-30 1973-08-14 Addressograph Multigraph Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287114A (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
US3752668A (en) * 1967-10-30 1973-08-14 Addressograph Multigraph Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers
US3556785A (en) * 1968-02-23 1971-01-19 Addressograph Multigraph Sensitizers for organic photoconductor comprising orazolone and butenolide derivatives of of fluorenone

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4105446A (en) * 1975-01-21 1978-08-08 Fuji Xerox Co., Ltd. Organic photoconductive coating compositions containing tricyanovinyl compounds for electrophotography
US4046564A (en) * 1975-07-16 1977-09-06 Xerox Corporation Electrophotographic imaging members with photoconductive layer containing electron acceptor monomers or polymers
US4050934A (en) * 1975-09-22 1977-09-27 Xerox Corporation Electron acceptor monomers and polymers
US4056391A (en) * 1975-09-22 1977-11-01 Xerox Corporation Method for enhancing solid solution stability of electron acceptor molecules and electrophotographic compositions
US4225692A (en) * 1975-09-22 1980-09-30 Xerox Corporation Electron acceptor monomers and polymers
US4063947A (en) * 1975-10-29 1977-12-20 Xerox Corporation Photoconductive insulating films comprising fluorenone-substituted oligomers
US4604295A (en) * 1983-12-22 1986-08-05 Loctite Corporation Visible light absorbing peroxy-esters
US4584253A (en) * 1984-12-24 1986-04-22 Xerox Corporation Electrophotographic imaging system
US5153085A (en) * 1988-10-05 1992-10-06 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
US6558851B1 (en) * 1999-10-28 2003-05-06 Holo Tech A.S. Optical medium for registration of holographic interferograms
US9145383B2 (en) 2012-08-10 2015-09-29 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US9611246B2 (en) 2012-08-10 2017-04-04 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US9765051B2 (en) 2012-08-10 2017-09-19 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US9867800B2 (en) 2012-08-10 2018-01-16 Hallstar Innovations Corp. Method of quenching singlet and triplet excited states of pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds have electron withdrawing groups, to reduce generation of reactive oxygen species, particularly singlet oxygen
US9926289B2 (en) 2012-08-10 2018-03-27 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
US10632096B2 (en) 2012-08-10 2020-04-28 HallStar Beauty and Personal Care Innovations Company Method of quenching singlet and triplet excited states of photodegradable pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds having electron withdrawing groups, to reduce generation of singlet oxygen
US9125829B2 (en) 2012-08-17 2015-09-08 Hallstar Innovations Corp. Method of photostabilizing UV absorbers, particularly dibenzyolmethane derivatives, e.g., Avobenzone, with cyano-containing fused tricyclic compounds
WO2014142844A1 (en) * 2013-03-13 2014-09-18 Hewlett-Packard Development Company, L.P. Organic photoconductors

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DE2401115A1 (de) 1974-07-18
JPS4994336A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1974-09-07

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