• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    A photosensitive member having at least two electrically operative layers is disclosed. The first layer comprises a photoconductive layer which is capable of photogenerating holes and injecting photogenerated holes into a contiguous charge transport layer. The charge transport layer comprises a polycarbonate resin containing from about 10 to about 75 percent by weight of: wherein X is selected from the group consisting of (ortho) CH3, (meta) CH3, (para) CH3, (ortho) C1, (meta) C1 and (para) C1. The charge transport layer while substantially non-absorbing in the spectral region of intended use is "active" in that it allows injection of photogenerated holes from the photoconductive layer, and allows these holes to be transported through the charge transport layer. This structure may be imaged in the conventional xerographic mode which usually includes charging, exposure to light and development.
    公开号:SU1378794A3
    申请号:SU772517594
    申请日:1977-08-22
    公开日:1988-02-28
    发明作者:Столка Милан；М.Пэй Дамодар；Ф.Янус Джон
    申请人:Ксерокс Корпорейшн (Фирма)；
    IPC主号:
    专利说明:

    with
    00

    with
    four
    The invention relates to electrophotographic elements for imaging and can be used in xerography for obtaining visible images.
    The aim of the invention is to improve the quality of the element by preventing the accumulation of residual potential.
    Example 1, Preparation of N, N-Diphenyl-N, N-bis (3-Meth-L-phenyl) -1, -biphenyl-4,4-diamine.
    A vessel with a capacity of 5000 ml with a round bottom and three necks, equipped with a mechanical stirrer and placed in an argon atmosphere, is used to prepare this compound. 336 g (I mol) N, n-diphenylbenzidine, 550 g (2.5 mol) m-iodotoluene, 550 g (2 mol) potassium carbonate (anhydrous), 50 g copper-bronze catalyst and 1500 ml dimethyl sulfoxide are placed in this vessel. (anhydrous). The heterogeneous mixture is heated under reflux for 6 days. The dark sludge is then filtered, the filtrate is extracted four times. Extracted with water, dried with magnesium sulfate and filtered. The benzene is removed under reduced pressure. The black product is segmented by column chromatography using neutral alumina. Colorless crystals are obtained by recrystallization of pro-product from n-octane. M.p. 167-169 ° C, yield 369 g (65%).
    EXAMPLE 2: A photosensitive layered structure contains an aluminum substrate on which a layer of amorphous selenium 1 μm thick and a layer 22 μm thick of a charge transfer material containing 25 wt.% N, N-diphenyl-S, k-bis are deposited. - (3-methylphenyl) - l, l-biphenyl-4,4-diamine and 75 mas. bis-phenol-A-polycarbonate, and this layer is applied over the layer of amorphous selenium. The element is made according to the following technology.
    A layer thickness of 1 micron from STEKLOVID-
    Selenium is formed on an aluminum substrate using vacuum technology.
    The charge transfer layer was prepared by dissolving 3.34 g of N, N -difensh-NN-bis (3-methylphenyl) -l, l-biphenyl-4,4-diamine prepared according to Example 1 in 135 g of methylene chloride, and 10 g of bisphenol-A-polycarbonate. The resulting mixture is applied to a layer of vitreous selenium using a film applicator. The coating is dried for about 18 to form a dry layer 22 microns thick, KOTOpbrti serves as a charge transfer layer.
    The cell is heated to 125 ° C for 16 hours, which is sufficient to convert vitreous selenium into trigonal crystalline selenium.
    The plate is electrically tested by applying a negative charge to the plate until the field reaches a value of 60 V / µm and is discharged using a light wavelength of 4200 X and an intensity of
    a.9.
    2x10 photons / cm. with. The plate provides satisfactory discharge and is suitable for use to form visible images.
    EXAMPLE 3. A photosensitive layered structure similar to that obtained in Example 1, containing an aluminum substrate on which a layer of trigonal selenium 1 μm thick was applied and a charge transfer layer of crowds {another 22 μm containing 50 wt.% N, N -diphenyl-K, H -bis (Z-methylphenyl) -1,1 -biphenyl 1-4,4-diamine and 50 wt.% bisphenol-A-polycarbonate, which is deposited on a layer of trigonal selenium. The element is made using the following technology.
    A 1 µm layer of amorphous selenium is vacuum evaporated onto an aluminum substrate (0.0762 mm) using conventional vacuum deposition technology. Prior to evaporation of amorphous selenium on a substrate, a barrier layer of epoxy phenolic resin with a thickness of 0.5 µm is formed on it by dip coating. Vacuum deposition is carried out at a vacuum of 1 ° Torr at a substrate temperature of 50 ° C. A layer thickness of 22 µm from charge transfer material containing 50% by weight N, n-diphenyl-S, (3-methylphenyl), 1-biphenyl-4 , 4 - diamine and 50 wt.% Poly (4,4-isopropylenediphenylene carbonate) with a molar mass of 40,000, is applied on a layer of amorphous selenium.
    权利要求:
    Claims (4)
    [1]
    I ...
    The charge transfer layer is made by dissolving in 135 g of methylene chloride 10 g N, N-diphenyl-N, N 10
     31378794
    bis (3-methylphenyl) -O-bnphenyl-4,4-diamine and 10 g of poly (4,4-isopropylidene diphenylene carbonate) mol. weighing about 40,000. The mixture is applied to an amorphous selenium layer using a film applicator. The coating is then dried for 18 hours to form a dry layer 22 microns thick of the charge transfer material. The layer of amorphous selenium is then transformed into a crystalline trigonal form by heating the entire device to 125 ° C and maintaining this temperature for about 16 hours. After 16 h, the device is cooled to room temperature. The plate is tested electrically using a negative charge to a field of 60 V / µm and a discharge with a length of 4200 A and intensity
    The charge transfer layer is made by dissolving in 135 g of chloromethylene 3.34 g of N, N-diphenyl-N, (3-methylphenyl) -, 1 -biphenyl j-4, diamine prepared according to example 1, and 10 g of bisphenyl -A-polycarbonate. A layer of the above mixture is formed on the glassy selenium-mouse-iodine layer. The coating is then dried under vacuum at 80 ° C for 18 hours to form a layer of charge transfer material with a thickness of 30 µm.
    15
    20
    light waves of 2x10 photons / cm C. The plate is discharged satisfactorily and can
    The plate is electrically tested using a negative charge to a value of 60 V / µm and a discharge
    its using the wavelength of light7
    that 4200 A at an intensity of 2x10 photons / cm - s. The plate is satisfactorily discharged and can be used to form visible images.
    P RIM e p 5. Preparation of N, N B flask with a capacity of 500 ml with three necks and a round bottom, supplied with 35
    40
    be used to obtain 25 diphenyl-N, N -bis (4-methylphenyl) -11, - high quality images. biphenyl-4,4-diamine.
    PRI me R 4. A photosensitive layered structure contains an aluminum substrate on which a layer 0.2 µm thick from amorphous selenium is deposited, a 30 "Wo magnetic stirrer and blown argon, 20 gp, p -diodobifile (0, 05 mol), 18.3 g of p-tolylphenylamine 0.1 mol), 20.7 g of potassium carbonate (anhydride) (O, 15 mol) 3, O g of powdered copper and 50 ml of sulpholane (tetrahydrothiophen-1 , 1-dioxide) The mixture is heated to 220-225 ° C for 24 hours, allowed to cool to approximately 150 ° C and 300 ml of deionized water are added. The heterogeneous mixture is heated under reflux with vigorous stirring. A light brown i oily precipitate forms in the flask. Water is decanted. 300 ml of water are then added and the water layer is decanted again. 300 ml of methanol is added and the mixture is heated under reflux to dissolve unreacted starting materials. The solid phase is filtered off, mixed with 300 ml of n-octane and heated under reflux to 125 C. The solution is filtered twice through 100 g of neutral alumina to obtain a pale yellow and then a colorless filtrate and allowed to cool. Colorless crystals of the desired compound are obtained.
    and a mouse, also containing halogen, and a layer 30 microns thick, from a material for transferring charges, containing 25% by weight of N, N-diphenyl-N, N-bccz-methylphenyl) -biphenylJ-4,4-diamine and 75 wt,% bisphenol-A-polycarbonate, which is deposited on a layer of amorphous selenium and halogen. The element is manufactured as follows.
    A mixture containing about 35.5% by weight of meat and 64.5% by weight. selenium and about 850 hours per million iodine, sealed in an ampoule and carried out the reaction at a temperature of about 525 ° C for 3 hours in a rotary kiln. The mixture is then cooled to room temperature, removed from the ampoule and placed in a quartz crucible in a glass bell at. The glass bell is then vacuumed to a pressure of about 5x10 Torr, and the quartz crucible is heated to f. To evaporate the mixture onto an aluminum plate. The crucible is maintained at an evaporation temperature for approximately 30 minutes. At the end of this time, the crucible is cooled and the resulting plate is removed from the cap.
    45
    55
    mp.163-164 S.
    0
    The charge transfer layer is made by dissolving in 135 g of chloromethylene 3.34 g of N, N-diphenyl-N, (3-methylphenyl) -, 1 -biphenyl j-4, diamine prepared according to example 1, and 10 g of bisphenyl -A-polycarbonate. A layer of the above mixture is formed on the glassy selenium-mouse-iodine layer. The coating is then dried under vacuum at 80 ° C for 18 hours to form a layer of charge transfer material with a thickness of 30 µm.
    The plate is electrically tested using a negative charge to a value of 60 V / µm and a discharge
    its using the wavelength of light7
    that 4200 A at an intensity of 2x10 photons / cm - s. The plate is satisfactorily discharged and can be used to form visible images.
    P RIM e p. 5. Preparation of N, N of diphenyl-N, N -bis (4-methylphenyl) -11, - biphenyl-4,4-diamine.
    B 500 ml flask with three necks and a round bottom, equipped with “Wo magnetic stirrer and purged-ap
    35
    g
    40
    g
    g
    45
    g
    55
    mp.163-164 S.
    PRI me R 6. N, N -Diphenyl-S, Y-bis (2-methylphenyl) - | I, l-biphenyl-1-A, 4-diamine.
    In a three-neck flask with a capacity of 250 ml with a round bottom, having a mechanical stirrer, a thermometer with a temperature regulator and a source of argon, is placed 8.4 g N, to diphenyl-1, 1-biphenyl 1-4,4-diamine (0.025 mol), 16.3 g of 2-iodotoluene (0.075 mol), 7.5 g of copper bronze and 24 ml of a mixture of C 5 aliphatic hydrocarbons, the contents of the flask are heated to I90 C with stirring for 18 h. An excess of 2-iodotoluene was removed by vacuum distillation using a water aspirator. The product is isolated by adding 200 ml of p-octane and hot filtration to remove the inorganic solid. Then a dark orange filtrate is column chromatographed using neutral alumina with cyclohexane benzene in the ratio 3: 2 as solvent for elution. The resulting oil was recrystallized from n-octane to give colorless crystals of the desired soybean, g of dinenium with mp. 148-150 S.,
    Example. N, N -Diphenyl-N, N-bis (3-chlorophenyl-1,1-biphenyl-4,4 - diamine.
    In a three-necked flask with a capacity of 150 ml with a round bottom, having a mechanical stirrer, a thermometer with a temperature regulator and a source of gaseous argon, 3.4 g of S are added, diphenyl-O 5 -biphenyl-4,4-diamine (0.01 mol , 5.6 g of potassium carbonate / 0.04 mol), 9.6 g of 3-chloroiodobenzene (0.04 mol) and 0.5 g of powdered copper. The contents of the flask are heated with stirring for 24 hours. Excess 3-chloroiodobenzene is removed by vacuum distillation using a water aspirator. The product is isolated by adding 200 ml of p-octane and filtering the inorganic phase. Column chromatography of the dark orange filtrate is carried out using neutral alumina with cyclohexane and benzene (as solvent for elution in 3: 2 ratio). The resulting oil is recrystallized from n-octane to obtain colorless crystals of the desired product with so pl. 130-1 32 s.
    50
    five
    0 5 Q g
    Example 8.N, N-biphenyl-K, N - bis (4-chlorophenyl), 1 -biphenyl-4, 4-diamine.
    In a three-necked flask with a capacity of 250 ml with a round bottom, having a fur. 3.4 g of N, N-diphenyl-1, l-biphenyl-4,4-di- are placed in a thermometer with a temperature regulator and a source of non-oxidizing gas. amine {o, 01 mol) and 0.5 g of copper. The contents of the flask are heated with stirring. over a 24 hour period. Using an aqueous aspirator, remove the excess of 4-chloroplastic by vacuum distillation. The product is isolated by the addition of 200 ml of p-octane and hot filtration to remove the inorganic solid. Column chromatography of the dark orange filtrate is carried out using neutral alumina with cyclohexane and benzene as eluent (3: 2). The resulting oil is recrystallized from n-octane to give colorless crystals of the desired product having mp 147-1 49 C.
    Example 9: Preparing an electrophotographic cell using the charge transfer compounds of the compounds prepared in Examples 5-8. Four solutions were prepared, each containing 1 g of polycarbonate dissolved in 13.5 g of methylene chloride. In each solution 1 g of the compounds prepared in examples 5-8 are dissolved. to obtain a 30% w / w solution of the solid phase of the compound in the polycarbonate after removal of methylene chloride.
    A layer of amorphous selenium 0.5 μm thick is evaporated on four aluminum square substrates from the side of the 50.8 mm square. Polycarbonate solutions of the compound of examples 5-8 are precipitated over selenium and dried under vacuum for 24 hours to obtain a layer with a thickness of 25 microns.
    Electrical tests of plates carried out analogously to examples 2-4 showed that charge transfer in these structures is comparable to the photosensitive structures of examples 3-A. In addition, each plate gives excellent xerographic copies.
    PRI me R 10. Preparation of known photoreceptor devices.
    Two separate combinations of N, N, N, N -tetraphenylvating radiation are prepared for approximately 30 of an electrically conductive substrate and
    35
    40
    but 2 ISS using light sources with a wavelength of 4330 A and an energy of 15 erg / cm.
    The cell discharges at the following rate: after 0.25 s, to approximately 900 V, after 0.50 s, to approximately 600 V, after 0.75 s, to approximately 500 V, after 1.00 s, to approximately 400 B, after 1.25 s - up to about 360 V, after 1.50 s - up to about 290 V, after 1.75 s - up to about 280.B, after 2.00 s - up to about 260 V, after 4 s Approximately 160 V.
    The nature of this element excludes its use in a real high-speed cyclic xerographic device.
    An element containing 20% by weight of a known compound is negatively charged to about -1425 V. The discharge rate in the dark is about 150 V over a time of 1.0 second. The charmed element is illuminated with a flash of an activating radiation ov of a source of 55 NICs with a wavelength of 4300 A and an energy of 15 erg / cm for about
    2 ISS. The element is discharged at the following speed: after 0.25 s, the fusible conductive layer with photogeneration and injection of holes, and the charge transfer layer adjacent to it, containing an electrically inactive organic resin based on polycarbonate and dispersed in it, diamnn fenilovogo ryda, distinguished with the fact that, in order to improve the quality of the element by preventing the accumulation of residual potential, it contains a compound of 45 forms as a diamine of a phenylnyl series ly
    50
    where X is C.-alkyl or chlorine, taken in an amount of 25-75% by weight.
    [2]
    2. Element by ri. 1, this is due to the fact that the photoconductor layer is made of amorphous or trigonal selenium or from an alloy of selenium with mice and iodine.
    a photoconductive layer deposited on it consistently with the photogeneration and injection properties of holes, and the charge transfer layer adjacent to it, containing an electrically inactive organic resin based on polycarbonate and dispersed in it a diam. so that, in order to improve the quality of the element by preventing the accumulation of residual potential, it contains, as a diamine of the phenyl series,
    55
    50
    where X is C.-alkyl or chlorine, taken in an amount of 25-75% by weight.
    2. Element by ri. 1, that is, with the fact that the photoconductor layer is made of amorphous or trigonal selenium or of selenium with mouse and iodine.
    91378794. ten
    [3]
    3. The element according to claims 1 and 2, about tl and -X is C 1 -C 6 alkyl or chlorine, taken up in that the layer is transferred in an amount of 25-75% by weight, the charge that is made contains g .Screen photoconductor layer of amorphous inactive organic resin on an axial or trigonal selenium or newer polycarbonate mol% 20,000 - of selenium alloy with mum lump and iodine, 120,000. Implementation of charge transfer layer from
    [4]
    4. Element pop.Z, I can distinguish electrically inactive resin on the basis of the fact that as a poly-nov polycarbonate mol. 20000- carbonate resin charge transfer layer - 120000.
    yes it contains poly (4, A-isopropylidene-. 04.05.77 (p.4) - use in
    diphenylene carbonate with mol.m. 35,000 - quality polycarbonate resin in
    40,000 or 40000-45000. Charge transfer layer of poly- (D, 4 -iso-Priority based on: propylidenediphenylene carbonate) with
    08.23.76 (p.1,2,3) - use-mol.m. from 35,000 to 40,000 or from
    the diamine of the phenyl series, where 40000 to 45000.
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    同族专利:
    公开号 | 公开日
    CA1104866A|1981-07-14|
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    MX148708A|1983-06-06|
    DE2734990A1|1978-03-09|
    FR2363134B1|1982-06-04|
    GB1577237A|1980-10-22|
    BR7705593A|1978-06-06|
    DE2734990C2|1986-12-11|
    NL7709279A|1978-02-27|
    MX171443B|1993-10-26|
    JPS5327033A|1978-03-13|
    FR2363134A1|1978-03-24|
    JPS599049B2|1984-02-29|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US71640376A| true| 1976-08-23|1976-08-23|
    US79381977A| true| 1977-05-04|1977-05-04|
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