US3837851A - Photoconductor overcoated with triarylpyrazoline charge transport layer - Google Patents

Photoconductor overcoated with triarylpyrazoline charge transport layer Download PDF

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Publication number
US3837851A
US3837851A US00323677A US32367773A US3837851A US 3837851 A US3837851 A US 3837851A US 00323677 A US00323677 A US 00323677A US 32367773 A US32367773 A US 32367773A US 3837851 A US3837851 A US 3837851A
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United States
Prior art keywords
charge
charge transport
transport layer
photoconductor
layer
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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
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US00323677A
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English (en)
Inventor
M Shattuck
W Weiche
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International Business Machines Corp
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International Business Machines Corp
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Publication date
Application filed by International Business Machines Corp filed Critical International Business Machines Corp
Priority to US00323677A priority Critical patent/US3837851A/en
Priority to IT41025/73A priority patent/IT1001106B/it
Priority to FR7345363A priority patent/FR2214139B1/fr
Priority to CH1750673A priority patent/CH579789A5/xx
Priority to CA188,761A priority patent/CA1005674A/en
Priority to GB49074A priority patent/GB1441996A/en
Priority to NL7400140A priority patent/NL7400140A/xx
Priority to JP49006089A priority patent/JPS592023B2/ja
Priority to DE2401219A priority patent/DE2401219C3/de
Priority to BE139772A priority patent/BE809704A/xx
Application granted granted Critical
Publication of US3837851A publication Critical patent/US3837851A/en
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
    • G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
    • G03G5/0436—Photoconductive layers characterised by having two or more layers or characterised by their composite structure combining organic and inorganic layers
    • 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
    • G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
    • G03G5/047—Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport layers
    • 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
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings

Definitions

  • ABSTRACT Electrophotographic plates having a charge generation layer and a separate charge transport layer comprising a tri-aryl pyrazoline compound having the formula:
  • n is Zero or one, and A, A and A are each aryl radicals.
  • the present invention is concerned with layered electrophotographic plates.
  • the charge transporting layer always comprises at least one tri-aryl pyrazoline compound having the formula:
  • n is zero or one, and A, A and A are each aryl radicals.
  • pyrazoline compounds useful in the present invention are known materials and their preparation has been described in the literature. The prior art teaches that such materials are known to be photoconductors. The photoconductive nature of pyrazolines is taught in U.S. Pat. Nos. 3,180,729 and 3,549,362.
  • pyrazoline compounds useful in the present invention are those having the formula wherein n is zero or one, and A, A and A are each aryl radicals.
  • n l in which case the materials may be classified chemically as styryl pyrazolines. It is also preferred that one or more of the aryl groups be substituted, most preferably with groups known in the art to be electron donating groups. The most preferred substituent groups are methoxy, ethoxy, dimethyl amino, diethyl amino an the like. It is not preferred to substitute the aryl groups with electron withdrawing groups such as nitro and cyano.
  • electrophotographic reproduction processes differ in the particular way in which they are carried out, particularly 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 charge transport layers of the present invention are useful in making electrophotographic plates useful in all such processes.
  • the charge transport layers may be used with any of a wide variety of separate charge generating layers.
  • the charge generating layer may be selenium or an alloy of selenium. It may be other inorganic materials such as compounds from groups II and VI of the periodic table, for example cadmium sulfo-selenide.
  • the charge generating material may be an organic material, for example a cyanine compound such as those shown in US. Pat. application Ser. No. 129,637, a disazo compound such as those shown in U.S. Pat. application Ser. No. 129,635, now abandoned, or a phthalocyanine compound. Particularly outstanding results have been obtained when the charge generating layer comprises a compound which is a methine dye derived from squaric acid. Materials of this type are discussed in U.S. Pat. application Ser. No. 323,678 filed on even date herewith.
  • the charge transport layers of the present invention 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.
  • the electrophotographic plate should be charged positively. The theoretical explanation for this is not known with certainty. It is theorized that the pyrazoline charge transport layers of the present invention operate by transporting holes, and this explanation would be consistent with those data.
  • Photoconductivity involves at least two steps: (1 the generation of charge, and (2) the transportation of charge.
  • the present invention utilizes the ability of the pyrazoline containing layer to transport the charge generated in the separate charge generating layer.
  • the pyrazoline containing materials have the unexpected ability not only to transport the charge, but also to accept injection of the charge, that is, to allow the charge to cross the interface between the separate charge generating layer and the charge transport layer. This is true with both organic and inorganic charge generation layers.
  • the pyrazoline compounds of the present invention have the additional advantage of being film forming. They may, therefore, be used by themselves to form the charge transport layer. For mechanical reasons, however, it is generally preferred to use them in conjunction with a binder. In most instances it is preferred to use roughly from about 1 part to about 3 parts by weight binder to one part by weight pyrazoline. Many types of binder materials such as resins are known to the prior art. Particularly good results have been obtained using polyester resins and polycarbonates. Polyvinylidene chloride and polystyrene may also be used, as may acrylic resins of low molecular weight.
  • EXAMPLE 1 A charge generating layer consisting of 68% Se, 30% Te, and 2% As (weight percent) evaporated on a conductive substrate which was dip coated with a barrier layer with a dry thickness of approximately 0.3 microns.
  • the barrier layer was coated with a solution of 3 parts polyester (Goodyear VPE 200) and 1 part lphenyl-3-[p-dimethylaminostyryl]-5-[p-dimethylaminophenyl]pyrazoline which had been dissolved in tetrahydrofuran. Method of coating was knife blade with a wet gap setting of 5 mils.
  • the composite layer was heated 16 hours at 55 C with a resulting dry thickness of 15 microns.
  • the photoconductor was corona charged in the dark to a negative voltage of approximately 700 volts.
  • the sample was then exposed to a light source of a photocopy green lamp.
  • the initial dark charge was reduced to 200 V with an exposure of 0.33 micro joules/cm?
  • EXAMPLE 2 A solution prepared from tetrahydrofuran and consisting of 3 parts of polyester and 1 part pyrazoline (as in Example No. 1) was knife blade coated at a wet thickness of 5 mils on a conductive substrate. The layer was dried for 2 hours at approximately 80C to remove excess solvent. Dry thickness was approximately 12 microns.
  • the photoconductor was charged on a rotating disc electrometer to a negative voltage of 600 volts.
  • Exposure to a tungsten source reduced the dark charge to 500 Volts (approximately 20 percent decay) after 4.0 seconds.
  • the layered photoconductor from Example No. l was dark charged on the rotating disc electrometer to a negative voltage of 880 V and exposed to the tungsten source plus a 1.47 neutral density filter plus opal glass.
  • the original dark charge of 880 was reduced 20 percent after 0.15 sec. (70X increase) and to a 200 volt level in 0.7 seconds.
  • EXAMPLE 3 Approximately 1 gram of a cyanine dye, 3-ethyl-2[5- '(3-ethyl-2-benzothiazolinylidene )-l ,S-pentadienyl] benzothiazolium iodide was placed in a McCrone micronizing mill (a vibro-energy laboratory mill available from McCrone Research Associates, London, England) and was ground as a dry powder for 60 minutes. Approximately grams of tetrahydrofuran and 0. 15 g of a polyvinylbutyral resin Vinylite XYHL (available from Union Carbide and Carbon Company) was added to the powder and was ground for an additional 30 minutes.
  • a McCrone micronizing mill a vibro-energy laboratory mill available from McCrone Research Associates, London, England
  • the resultant slurry was reduced in concentration by additional tetrahydrofuran and was applied to an volts.
  • the sample was exposed to a tungsten light source filtered with wavelength filters to give maximum intensity at approximately 5.500 angstroms.
  • the initial dark voltage of 700 volts was reduced to 200 volts by an exposure of approximately 07 micro joules/cm".
  • EXAMPLE 4 A selenium alloy charge generating layer was prepared in the same manner as Example No. I The layer was dip coated with a solution of one part polyester and one part l-phenyl-3-[p-methoxystyryl]-5-[p'methoxy phenyll-pyrazoline dissolved in tetrahydrofuran. The coating was dried for 40 hours at C to remove excess solvent with a resulting dry thickness of 16 to 18 microns.
  • a selenium alloy charge generating layer was prepared in the same manner as Example No. l. The layer was dip coated with a solution of two parts polyester and one part l-phenyl-3-[p-diethylaminostyryl]-5-[pdiethylaminophenyl]-pyrazoline dissolved in tetrahydrofuran. The coating was dried for 72 hours at C to remove excess solvent with a resulting dry thickness of 15 microns.
  • the photoconductor was corona charged in the dark to a negative charge of 700 volts and then was exposed to a photo-copy green lamp. The initial dark charge was reduced to 200 volts with an exposure of 0.24 micro joules/cm?
  • EXAMPLE 6 A charge generating layer consisting of a Se alloy was evaporated directly onto a conductive substrate. A charge transport layer was formulated and coated in the same manner as Example No. 5.
  • a charge generating layer consisting of Cd S Se approximately 0.3 microns thick was coated on a conductive substrate by a chemical vapor deposition technique.
  • a charge transport layer consisting of 3 parts polyester and one part l-phenyl-3-[ pdimethylaminostyry] ]-5 -[p-dimethylamino phenyl]- pyrazoline was knife coated to a dry thickness of approximately six microns.
  • the photoconductor was dark charged on a rotating disc electrometer to a negative charge of 390 volts.
  • the sample was exposed to a tungsten source with the initial dark charge being reduced to 200 volts in 0.15 sec.
  • EXAMPLE 8 A charge transport layer consisting of two parts polyester and one part l-phenyl-3[p-diethylaminostyryl1- S-[p-diethylamino phenyH-pyrazoline was dissolved in a suitable solvent. The solution was dip coated in a conductive substrate and dried to an approximate thickness of microns. A charge generating layer consisting of 2-p-dimethylaminostyrylquinoline ethiodide dye was rubbed onto the surface of the transport layer (thickness, less than 2 microns).
  • the photoconductor was then positively charged on a rotating disk electrometer to a dark charge of 720 volts.
  • the initial dark charge was decayed with a tungsten lamp to 200 volts in 0.80 seconds.
  • EXAMPLE 9 A second charge transport layer prepared in the same manner as in Example No. 7 was coated with a thin dye layer of pyrazlone red.
  • the photoconductor was positively charged to a dark voltage of 920 volts on the rotating disc electrometer.
  • the initial dark voltage was then reduced with a tungsten exposure source to 200 volts in 0.70 seconds.
  • An electrophotographic process comprising the steps of negatively charging and image-wise exposing to light an electrophotographic plate comprising a conductive substrate, a layer comprising a photoconductor selected from the group consisting of selenium and its alloys, compounds of an element from Group II and an element from Group VI of the periodic table, cyanine compounds, disazo compounds, and phthalocyanine compounds, and, overcoating said layer of photoconductor, a separate layer from 10 to 30 microns thick comprising a compound having the formula:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Photoreceptors In Electrophotography (AREA)
US00323677A 1973-01-15 1973-01-15 Photoconductor overcoated with triarylpyrazoline charge transport layer Expired - Lifetime US3837851A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US00323677A US3837851A (en) 1973-01-15 1973-01-15 Photoconductor overcoated with triarylpyrazoline charge transport layer
IT41025/73A IT1001106B (it) 1973-01-15 1973-11-28 Piastre elettrofotografiche strati ficate
FR7345363A FR2214139B1 (it) 1973-01-15 1973-12-11
CH1750673A CH579789A5 (it) 1973-01-15 1973-12-14
CA188,761A CA1005674A (en) 1973-01-15 1973-12-21 Layered electrophotographic plates
GB49074A GB1441996A (en) 1973-01-15 1974-01-04 Layered electrophotographic elements
NL7400140A NL7400140A (it) 1973-01-15 1974-01-07
JP49006089A JPS592023B2 (ja) 1973-01-15 1974-01-11 電子写真板
DE2401219A DE2401219C3 (de) 1973-01-15 1974-01-11 Elektrophotographisches Aufzeichnungsmaterial
BE139772A BE809704A (fr) 1973-01-15 1974-01-14 Plaque electrophotographique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00323677A US3837851A (en) 1973-01-15 1973-01-15 Photoconductor overcoated with triarylpyrazoline charge transport layer

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US (1) US3837851A (it)
JP (1) JPS592023B2 (it)
BE (1) BE809704A (it)
CA (1) CA1005674A (it)
CH (1) CH579789A5 (it)
DE (1) DE2401219C3 (it)
FR (1) FR2214139B1 (it)
IT (1) IT1001106B (it)
NL (1) NL7400140A (it)

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Also Published As

Publication number Publication date
DE2401219A1 (de) 1974-07-25
DE2401219B2 (de) 1975-03-27
FR2214139A1 (it) 1974-08-09
CA1005674A (en) 1977-02-22
FR2214139B1 (it) 1977-06-10
IT1001106B (it) 1976-04-20
BE809704A (fr) 1974-05-02
CH579789A5 (it) 1976-09-15
JPS592023B2 (ja) 1984-01-17
JPS49105537A (it) 1974-10-05
DE2401219C3 (de) 1975-11-27
NL7400140A (it) 1974-07-17

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