US3824099A - Sensitive electrophotographic plates - Google Patents

Sensitive electrophotographic plates Download PDF

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Publication number
US3824099A
US3824099A US00323678A US32367873A US3824099A US 3824099 A US3824099 A US 3824099A US 00323678 A US00323678 A US 00323678A US 32367873 A US32367873 A US 32367873A US 3824099 A US3824099 A US 3824099A
Authority
US
United States
Prior art keywords
charge
layer
transport layer
squaric acid
electrophotographic plates
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
US00323678A
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English (en)
Inventor
R Champ
M Shattuck
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.)
IBM Information Products Corp
Original Assignee
International Business Machines Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by International Business Machines Corp filed Critical International Business Machines Corp
Priority to US00323678A priority Critical patent/US3824099A/en
Priority to FR7345362A priority patent/FR2214138B1/fr
Priority to GB49074A priority patent/GB1441996A/en
Priority to DE2401220A priority patent/DE2401220A1/de
Priority to JP49006088A priority patent/JPS524188B2/ja
Application granted granted Critical
Publication of US3824099A publication Critical patent/US3824099A/en
Assigned to IBM INFORMATION PRODUCTS CORPORATION, 55 RAILROAD AVENUE, GREENWICH, CT 06830 A CORP OF DE reassignment IBM INFORMATION PRODUCTS CORPORATION, 55 RAILROAD AVENUE, GREENWICH, CT 06830 A CORP OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: INTERNATIONAL BUSINESS MACHINES CORPORATION
Assigned to MORGAN BANK reassignment MORGAN BANK SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IBM INFORMATION PRODUCTS CORPORATION
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • G03G5/0611—Squaric acid
    • 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
    • G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms

Definitions

  • Very sensitive electrophotographic plates having a charge generating layer comprising a squaric acid methine dye and a charge transport layer comprising a tri-aryl pyrazoline compound.
  • the present invention is concerned with electrophotographic plates.
  • it is concerned with layered plates having a charge generation layer and a separate charge transport layer.
  • the charge generation layer comprises a squaric acid methine dye and the charge transport layer comprises a tri-aryl pyrazoline compound. Electrophotographic plates containing these layers have been found to be extremely sensitive to light.
  • Squaric Acid methine dyes are known compounds which have been described in the literature. 1,3- and 1,2-squaric acid methine dyes, both of which are useful in the present invention, have been described, for example, in US. Pat. 3,617,270 where methods for their synthesis are also described. That patent discloses the use of squaric acid methine dyes for the optical sensitization of zinc oxide, in which use the squaric acid methine dye is used at a concentration of about 0.1 to 20 milligrams per square meter of finished photoconductive layer.
  • the electrophotographic plates of the present invention comprise, in addition to a conductive substrate, a charge generating layer containing a squaric acid methine dye and a separate charge transport layer containing a tri-aryl pyrazoline compound.
  • Electrophotographic plates having the structure recited above have been found to be extremely fast in their response to light. They are panchromatic out to about 7000 Angstrom units. They are also responsive to light having wave lengths up to 9000 Angstroms. A particularly suitable field for their use is with lasers having wave lengths of from about 8000 to about 9000 Angstrorns.
  • the electrophotographic plates contain both squaric acid charge generating material and tri-aryl pyrazoline charge transporting material. Both are essential elements of the present invention. This result was totally unexpected and the theoretical explanation for it is not known.
  • electrophotographic reproduction processes there are several well known electrophotographic reproduction processes in current use. They differ in the particular way in which they are carried out, particularly United States Patent 0 ice in the sequence in which electric charging (usually with a corona) and illumination are carried out. All electrophotographic reproduction processes, however, involve the process step of selectively rendering portions of a photoconductor electrically conductive by selective exposure to light. The electrophotographic plates of the present invention are useful in all such processes.
  • the charge transport layer may be used either on top of the charge generating layer, or beneath the charge generating layer. For mechanical reasons, it is generally preferred that the charge transport layer be on top.
  • the charge transport layer may vary considerably in thickness, in general being from about 10 to about 30 microns thick, preferably from about 15 to about 25.
  • the electrophotographic plate should be charged negatively. In those instances where the charge transport layer is beneath the charge generating layer, that is, when the charge transport layer is between the charge generating layer and the conductive substrate, the electrophotographic plate should be charged positively.
  • the squaric acid methine dye maybe used alone, but it is preferred to use a squaric acid methine dye in conjunction with a binder when the layer is formed by coating from a slurry.
  • the optimum ratio of dye to binder is generally from about 0.1 to about 0.9.
  • Binderless layers may be formed by vacuum evaporation. Many types of binder materials, such as resins, are known to the prior art. Many polyesters are suitable materials. Sucrose benzoate may also be employed in many mixtures of the various, binders. Particularly outstanding results have been obtained using polyvinyl butyral.
  • the charge generating layer be from about 0.1 to about 2 microns thick, most preferably about 0.5 microns. It is also preferred that the charge generating layer contain from approximately 50 to about 100 milligrams of the squaric acid methine dye per square meter of plate area.
  • the following squarylium pigments were all ground to a fine particle size in tetrahydrofuran and applied by a knife blade coater on aluminized Mylar substrate.
  • Mylar is a trade name for polyethyleneterephthalate film from Dupont.
  • the coating percent solids is 3% and the wet gap setting is one mil.
  • a transport layer of 2 parts Merlon 60 and 1 part DEASP by weight Coating thickness is 13-15 microns thick.
  • Merlon 60 is a trade name for a polycarbonate resin marketed by Mobay Chemicals.
  • DEASP is a shortened abbreviation for 1-Phenyl-3-[pdiethylaminostyryH-S [p-diethylamino phenyl]-pyrazoline.
  • the coated films are then heated for 30 minutes electrometer.
  • the illumination was from a tungsten halogen lamp, watts, 28 volts at a distance of approximately .5 cm.
  • HO- OH l CH3 HI E- A is the amount of energy required to decay the photoconductor by exposure to light to one-half its charge acceptance.
  • the percent solids is 15.5 and the coating speed is 8 f.p.m.
  • the fihn is treated for 15 minutes at 115 C.
  • EXAMPLE 12 When the formulation of Example 9 is coated on aluminized Mylar which has been subbed with a coating of 0.3;]. of an acrylic resin (A-11 from Roehm and Haas) the following sensitometric data are noted:
  • EXAMPLE 13 The charge generating layer was prepared by evaporating the compound in Example 11 on an aluminized Mylar substrate to an optical density to green light of 0.4.
  • An electrophotographic plate comprising a conductive substrate, a layer comprising a squaric acid methine dye and a separate layer comprising a tri-aryl pyrazoline compound.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Photoreceptors In Electrophotography (AREA)
US00323678A 1973-01-15 1973-01-15 Sensitive electrophotographic plates Expired - Lifetime US3824099A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US00323678A US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates
FR7345362A FR2214138B1 (fr) 1973-01-15 1973-12-11
GB49074A GB1441996A (en) 1973-01-15 1974-01-04 Layered electrophotographic elements
DE2401220A DE2401220A1 (de) 1973-01-15 1974-01-11 Elektrophotographische platte
JP49006088A JPS524188B2 (fr) 1973-01-15 1974-01-11

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00323678A US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates

Publications (1)

Publication Number Publication Date
US3824099A true US3824099A (en) 1974-07-16

Family

ID=23260256

Family Applications (1)

Application Number Title Priority Date Filing Date
US00323678A Expired - Lifetime US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates

Country Status (4)

Country Link
US (1) US3824099A (fr)
JP (1) JPS524188B2 (fr)
DE (1) DE2401220A1 (fr)
FR (1) FR2214138B1 (fr)

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US3964904A (en) * 1974-08-22 1976-06-22 Xerox Corporation Manifold imaging member and process employing a dark charge injecting layer
US4030923A (en) * 1975-12-11 1977-06-21 International Business Machines Corporation Mixture of binder materials for use in connection with a charge transport layer in a photoconductor
US4052209A (en) * 1975-03-07 1977-10-04 Minnesota Mining And Manufacturing Company Semiconductive and sensitized photoconductive compositions
US4090782A (en) * 1977-05-31 1978-05-23 International Business Machines Corporation Electrochromic display devices comprising thienylidene pyrazoline compounds
US4093358A (en) * 1976-12-27 1978-06-06 International Business Machines Corporation High efficiency electrochromic display device
US4123270A (en) * 1975-09-15 1978-10-31 International Business Machines Corporation Method of making electrophotographic imaging element
US4142783A (en) * 1977-05-31 1979-03-06 International Business Machines Corporation Reversible electrochromic display device having memory
US4175956A (en) * 1978-02-10 1979-11-27 Eastman Kodak Company Electrophotosensitive materials for migration imaging processes
US4307167A (en) * 1980-03-03 1981-12-22 International Business Machines Corporation Layered electrophotographic plate having tetramethyl benzidene based disazo dye
US4314016A (en) * 1979-06-20 1982-02-02 Ricoh Co., Ltd. Electrophotographic element having a bisazo photoconductor
US4363859A (en) * 1977-10-22 1982-12-14 Ricoh Company, Ltd. Electrophotographic photoconductor
US4381337A (en) * 1981-11-23 1983-04-26 Pitney Bowes Inc. Polyester adhesive layer for photosensitive elements
US4389475A (en) * 1981-03-20 1983-06-21 Basf Aktiengesellschaft Multilayered electrophotographic recording medium
US4413045A (en) * 1981-05-26 1983-11-01 Canon Kabushiki Kaisha Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer
US4418133A (en) * 1981-03-27 1983-11-29 Canon Kabushiki Kaisha Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer
US4423129A (en) * 1980-12-17 1983-12-27 Canon Kabushiki Kaisha Electrophotographic member having layer containing methylidenyl hydrazone compound
US4446217A (en) * 1981-02-03 1984-05-01 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a hydrazone containing layer
US4456671A (en) * 1981-12-23 1984-06-26 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound
US4471041A (en) * 1983-05-09 1984-09-11 Xerox Corporation Photoconductive devices containing novel squaraine compositions
US4481272A (en) * 1981-03-20 1984-11-06 Basf Aktiengesellschaft Layered electrophotographic recording medium comprising heterocyclic nitrogen containing organic dye compounds
US4481270A (en) * 1983-04-28 1984-11-06 Ricoh Systems, Inc. Photoreceptor containing squaric acid methine dyes
US4486520A (en) * 1983-12-05 1984-12-04 Xerox Corporation Photoconductive devices containing novel squaraine compositions
US4487824A (en) * 1982-05-17 1984-12-11 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a halogen substituted hydrazone
US4500621A (en) * 1983-04-11 1985-02-19 Ricoh Systems, Inc. Sensitive electrophotographic plates containing squaric acid methine dyes suspended in a binder
US4507480A (en) * 1983-05-09 1985-03-26 Xerox Corporation Squaraines
US4508811A (en) * 1983-01-17 1985-04-02 U.S. Philips Corporation Recording element having a pyrylium or thiopyrylium-squarylium dye layer and new pyrylium or thiopyrylium-squarylium compounds
US4508803A (en) * 1983-12-05 1985-04-02 Xerox Corporation Photoconductive devices containing novel benzyl fluorinated squaraine compositions
US4523035A (en) * 1983-12-05 1985-06-11 Xerox Corporation Process for synthesizing squaraine compositions
US4524218A (en) * 1984-01-11 1985-06-18 Xerox Corporation Processes for the preparation of squaraine compositions
EP0146301A1 (fr) * 1983-12-05 1985-06-26 Xerox Corporation Procédé de synthèse de compositions de squaraine
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US20060210895A1 (en) * 2003-06-03 2006-09-21 Takatsugu Obata Photosensitive material for electrophotography and image forming device having the same
US20060215805A1 (en) * 2003-08-13 2006-09-28 Louis Aerts Sealing device for the outer surface of a nuclear fuel cladding
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US20070281229A1 (en) * 2006-06-02 2007-12-06 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus
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US20120248419A1 (en) * 2011-02-09 2012-10-04 Mark Thompson Organic photosensitive devices comprising aryl squaraines and methods of making the same
US8465890B2 (en) 2010-08-30 2013-06-18 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus including the same, and coating solution for undercoat layer formation in electrophotographic photoconductor
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Also Published As

Publication number Publication date
JPS524188B2 (fr) 1977-02-02
DE2401220A1 (de) 1974-07-25
JPS49105536A (fr) 1974-10-05
FR2214138A1 (fr) 1974-08-09
FR2214138B1 (fr) 1977-06-10

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