EP0397146B1 - Matériau photosensible pour électrophotographie du type laminé - Google Patents

Matériau photosensible pour électrophotographie du type laminé Download PDF

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Publication number
EP0397146B1
EP0397146B1 EP90108738A EP90108738A EP0397146B1 EP 0397146 B1 EP0397146 B1 EP 0397146B1 EP 90108738 A EP90108738 A EP 90108738A EP 90108738 A EP90108738 A EP 90108738A EP 0397146 B1 EP0397146 B1 EP 0397146B1
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EP
European Patent Office
Prior art keywords
charge
transporting
photosensitive material
electrophotography
weight
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
EP90108738A
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German (de)
English (en)
Other versions
EP0397146A3 (fr
EP0397146A2 (fr
Inventor
Hiroaki Iwasaki
Youichi Takesawa
Hiroshi Takemoto
Masashi Tanaka
Keizo Kimoto
Tadashi Sakuma
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.)
Kyocera Mita Industrial Co Ltd
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Mita Industrial Co Ltd
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Publication date
Priority claimed from JP1114308A external-priority patent/JPH02293853A/ja
Priority claimed from JP31364589A external-priority patent/JPH06103394B2/ja
Application filed by Mita Industrial Co Ltd filed Critical Mita Industrial Co Ltd
Publication of EP0397146A2 publication Critical patent/EP0397146A2/fr
Publication of EP0397146A3 publication Critical patent/EP0397146A3/fr
Application granted granted Critical
Publication of EP0397146B1 publication Critical patent/EP0397146B1/fr
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    • 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
    • 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

Definitions

  • the present invention relates to a laminate type photosensitive material for the electrophotography, which comprises a charge-generating layer and a charge-transporting layer, which are formed on an electroconductive substrate.
  • a laminate type photosensitive material having the above-mentioned structure has been publicly known as the so-called function-separated photosensitive material.
  • a substance having a higher ionization potential than that of the charge-transporting substance is used as the charge-generating substance.
  • the charge-generating material and the charge-transporting material are used in the above-mentioned combination, when the photosensitive material is used repeatedly, the stability of the surface potential is bad.
  • Another object of the present invention is to provide a laminate type photosensitive material for the electrophotography, in which the stability at the repeated use is improved by preventing the deterioration by light or heat.
  • a laminate type photosensitive material for the electrophotography which comprises a charge-generating layer and a charge-transporting layer, which are formed on an electroconductive substrate, wherein the charge-transporting layer comprises a first charge-transporting material having an ionization potential smaller than that of a charge-generating material used for the charge-generating layer and a second charge-transporting material having an ionization potential larger than that of the charge-generating material.
  • the present invention is prominently characterized in that a charge-transporting material having an ionization potential smaller than that of an charge-generating material used for the charge-generating layer and a charge-transporting material having an ionization potential larger than that of the charge-generating material are used in combination as the charge-transporting material constituting the charge-transporting layer.
  • Fig. 1 is a graph illustrating the relations of the ratio of the combined charge-transporting materials to the quantity of reduction of the surface potential and the residual potential.
  • Fig. 2 is a diagram illustrating an apparatus for use in the electrophotographic characteristics of a photosensitive material.
  • the laminate type photosensitive material of the present invention comprises an electroconductive substrate, a charge-generating layer formed on the substrate and a charge-transporting layer formed on the charge-generating layer.
  • a sheet or drum formed of a foil or sheet of a metal such as aluminum, copper or tin or a tin plate is used as the electroconductive substrate.
  • a substrate formed by depositing a metal as mentioned above on a film substrate such as a biaxially drawn polyester film or a glass substrate by vacuum deposition, sputtering or electroless plating can be used.
  • a film substrate such as a biaxially drawn polyester film or a glass substrate by vacuum deposition, sputtering or electroless plating
  • an electroconductively treated paper sheet can be used.
  • the charge-generating layer formed on the above-mentioned electroconductive substrate is formed of a dispersion of a charge-generating material in an electrically insulating binder resin.
  • Known electrically insulating materials can be used.
  • a polyester resin an acrylic resin, a styrene resin, an epoxy resin, a silicone resin, an alkyd resin and a vinyl chloride/vinyl acetate copolymer resin can be used.
  • any of materials capable of generating carriers on receipt of light known in the field of the electrophotography, can be used as the charge-generating material.
  • a phthalocyanine pigment for example, there can be mentioned a phthalocyanine pigment, a perylene pigment, a quinacridone pigment, a pyranthrone pigment, a disazo pigment and a trisazo pigment.
  • the charge-generating material is finely dispersed in the form of particles having a particle size smaller than 5 ⁇ m in the binder resin, and the charge-generating material is used in an amount of 5 to 100 parts by weight, especially 10 to 50 parts by weight, per 100 parts by weight of the binder resin.
  • the charge-generating layer is formed in a thickness of 0.05 to 3 ⁇ m, especially 0.3 to 1 ⁇ m.
  • the charge-transporting layer formed on the charge-generating layer is formed of a dispersion of a charge-transporting material in a binder resin as described above with respect to the charge-generating layer.
  • a first charge-transporting material having an ionization potential smaller than that of the used charge-generating material and a second charge-generating material having an ionization potential larger than that of the used charge-generating material are used in combination as the charge-transporting material.
  • charge-transporting materials can be used in the present invention, and two kinds of charge-generating materials satisfying the above requirement are used in combination.
  • each of the ionization potentials of the first and second charge-transporting materials from that of the charge-generating material be within ⁇ 0.2 eV.
  • the ionization potential of the first charge-transporting material is too small, the reduction of the surface potential is too large, and if the ionization potential (abbreviated to "Ip" hereinafter) of the second charge-transporting material is too large, the injection of holes becomes difficult and the accumulation of residual charges tends to increase.
  • first charge-transporting material and second charge-transportion material be used in such amounts that the weight ratio of the first charge-transporting material to the second charge-transporting material be from 10/90 to 90/10, especially from 30/70 to 70/30.
  • the charge-transporting materials are used in a total amount of 50 to 300 parts by weight, especially 70 to 100 parts by weight, per 100 parts by weight of the binder resin.
  • phenol type antioxidant that can be used in the present invention, there can be mentioned 2,6-t-butyl-p-cresol, triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)] propionate, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonate and 4,4′-thiobis(3-methyl-6-t-butylphenol).
  • phenol type antioxidants can be used singly or in the form of mixtures of two or more of them.
  • octadecyl-3-(3,5-di-t-butyl-4-hydroxydiphenyl) propionate and bis(1,2,2,6,6-pentamethyl-4-piperidyl) 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butyl-malonate are preferably used.
  • the phenol type antioxidant is used in an amount of 5 to 50 parts by weight per 100 parts by weight of the binder resin. If the amount used of the phenol type antioxidant exceeds 50 parts by weight, the sensitivity is reduced and the residual potential rises at the repeated use. If the amount of the phenol type antioxidant is smaller than 5 parts by weight, a sufficient stability of the surface potential cannot be obtained at the repeated use.
  • the charge-transporting layer is formed in a thickness of 10 to 30 ⁇ m, especially 15 to 20 ⁇ m.
  • a ball mill was charged with 100 parts by weight polyvinyl butyral (S-Lec BL1 supplied by Sekisui Kagaku) as the binder, 200 parts by weight of metal-free phthalocyanine as the charge-generating material and a predetermined amount of tetrahydrofuran, and the mixture was stirred for 24 hours to form a charge-generating layer-forming coating liquid.
  • the obtained coating liquid was coated on an aluminum drum by the dipping method and dried with hot air at 110°C for 30 minutes to effect curing and form a charge-generating layer having a thickness of 0.5 ⁇ m.
  • a homomixer 100 parts by weight of a polycarbonate resin (Upiron supplied by Mitsubishi Gas Kagaku) as the binder, 70 parts by weight of N,N′-bis(o,p-dimethylphenyl)-N,N′-(diphenyl)benzidine (hereinafter referred to as "4Me-TPD") and 30 parts by weight of 1,1-bis(p-diethylaminophenyl)-4,4-diphenyl-1,3-butadiene (hereinafter referred to as "T-405") as the charge-transporting material, and a predetermined amount of toluene were mixed and stirred to form a charge-transporting layer-forming coating liquid.
  • a polycarbonate resin Upiron supplied by Mitsubishi Gas Kagaku
  • the coating liquid was coated on the surface of the charge-generating layer by the dipping method and dried with hot air at 110°C for 30 minutes to form a charge-transporting layer having a thickness of about 20 ⁇ m.
  • a photosensitive material for the electrophotography was prepared.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting material was changed to 60 parts by weight of 4Me-TPD and 40 parts by weight of T-405.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting layer was changed to 50 parts by weight of 4Me-TPD and 50 parts by weight of T-405.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting layer was changed to 40 parts by weight of 4Me-TPD and 60 parts by weight of T-405.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting layer was changed to 30 parts by weight of 4Me-TPD and 70 parts by weight of T-405.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that 70 parts by weight of 4Me-TPD and 30 parts by weight of 4-(N,N-diethylamino)benzaldehyde-N,N-diphenylhydrazone instead of T-405 were used as the charge-transporting material for the formation of the charge-transporting layer.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting layer was changed to 100 parts by weight of 4Me-TPD.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that the charge-transporting material used for the formation of the charge-transporting layer was changed to 100 parts by weight of T-405.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 1 except that 5 parts by weight of 2,6-di-t-butyl-p-cresol (BHT supplied by Kawaguchi Kagaku) was added as the phenol type antioxidant.
  • BHT 2,6-di-t-butyl-p-cresol
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 25 parts by weight of 2,6-di-t-butyl-p-cresol (BHT supplied by Kawaguchi Kagaku) was used as the phenol type antioxidant.
  • BHT 2,6-di-t-butyl-p-cresol
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 50 parts by weight of 2,6-di-t-butyl-p-cresol (BHT supplied by Kawaguchi Kagaku) was used as the phenol type antioxidant.
  • BHT 2,6-di-t-butyl-p-cresol
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 5 parts by weight of triethylene glycol bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate] (Irganox 245 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 25 parts by weight of triethylene glycol bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate] (Irganox 245 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 50 parts by weight of triethylene glycol bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate] (Irganox 245 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 5 parts by weight of octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate (Irganox 1076 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 25 parts by weight of octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate (Irganox 1076 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 50 parts by weight of octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate (Irganox 1076 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 5 parts by weight of bis(1,2,2,6,6-pentamethyl-4-piperidyl 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonate (Tinuvin 144 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 25 parts by weight of bis(1,2,2,6,6-pentamethyl-4-piperidyl 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butyl-malonate (Tinuvin 144 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 50 parts by weight of bis(1,2,2,6,6-pentamethyl-4-piperidyl 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonate (Tinuvin 144 supplied by Ciba-Geigy) was used as the phenol type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 10 parts by weight of 4,4′-isopropylidene-diphenol alkyl (C12 to C15) phosphite (Mark 1500 supplied by Adeca-Argus) was used as the phosphorus type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 10 parts by weight of diisodecyl pentaerythritol diphosphite (Himo supplied by Sanko Kagaku) was used as the phosphorus type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 10 parts by weight of 1,3-bis(dimethylaminopropyl-2-thiourea (Nolax NS10 supplied by Ouchi Shinko Kagaku) was used as the amine type antioxidant.
  • a photosensitive material for the electrophotography was prepared in the same manner as described in Example 7 except that 10 parts by weight of bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate (Sanol 770 supplied by Sankyo Kagaku) was used as the amine type antioxidant. (Evaluation of Photosensitive Materials for Electrophotography).
  • Photographic characteristics such as the charging capacity and residual potential were measured by using an apparatus as shown in Fig. 2.
  • a photosensitive material 5 obtained in each example was negatively charged by carrying out corona discharge under -6 kV by using Corontron 1 while rotating the photosensitive material 5, and the surface potential V SP (V) was measured by a surface potentiometer arranged at a position 7.
  • the surface potential V 100SP (V) was measured after 100 cycles of the above-mentioned electrophotographic process and the difference ⁇ V SP (V) between this surface potential and the initial surface potential V SP (V) of the photosensitive material was calculated.
  • the photosensitive material of Comparative Example 1 had a high residual potential, though the stability of the surface potential at the repeated use was good.
  • the photosensitive material of Comparative Example 2 had no stability of the surface potential at the repeated use, though the residual potential was low.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Claims (4)

  1. Matériau photosensible de type stratifié pour l'électrophotographie, qui comprend une couche engendrant des charges et une couche de transport de charges, qui sont formées sur un substrat électroconducteur, caractérisé en ce que la couche de transport de charges comprend un premier matériau de transport de charges ayant un potentiel d'ionisation plus faible que celui d'un matériau engendrant des charges utilisé pour la couche engendrant des charges et un second matériau de transport de charges ayant un potentiel d'ionisation plus élevé que celui du matériau engendrant des charges.
  2. Matériau photosensible pour l'électrophotographie selon la revendication 1, caractérisé en ce que les différences des potentiels d'ionisation des premiers et seconds matériaux de transport de charges à partir du potentiel d'ionisation du matériau engendrant des charges sont dans la gamme de ± 0,2 eV.
  3. Matériau photosensible pour l'électrophotographie selon la revendication 1 ou 2, caractérisé en ce que les premiers et seconds matériaux de transport de charges sont utilisés en des quantités telles que le rapport pondéral entre le premier matériau de transport de charges et le deuxième matériau de transport de charges vaut de 10:90 à 90:10.
  4. Matériau photosensible pour l'électrophotographie selon l'une quelconque des revendications 1 à 3, caractérisé en ce que la couche de transport de charges comprend les premiers et seconds matériaux de transport de charges et un antioxydant de type phénol.
EP90108738A 1989-05-09 1990-05-09 Matériau photosensible pour électrophotographie du type laminé Expired - Lifetime EP0397146B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP114308/89 1989-05-09
JP1114308A JPH02293853A (ja) 1989-05-09 1989-05-09 積層型電子写真用感光体
JP31364589A JPH06103394B2 (ja) 1989-11-30 1989-11-30 積層型電子写真用感光体
JP313645/89 1989-11-30

Publications (3)

Publication Number Publication Date
EP0397146A2 EP0397146A2 (fr) 1990-11-14
EP0397146A3 EP0397146A3 (fr) 1991-04-24
EP0397146B1 true EP0397146B1 (fr) 1994-08-03

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP90108738A Expired - Lifetime EP0397146B1 (fr) 1989-05-09 1990-05-09 Matériau photosensible pour électrophotographie du type laminé

Country Status (4)

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EP (1) EP0397146B1 (fr)
KR (1) KR960010180B1 (fr)
CA (1) CA2016257C (fr)
DE (1) DE69011185T2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994013A (en) * 1998-04-24 1999-11-30 Lexmark International, Inc. Dual layer photoconductors with charge generation layer containing charge transport compound

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5767934A (en) * 1980-10-16 1982-04-24 Konishiroku Photo Ind Co Ltd Electrophotographic receptor
JPS58105234A (ja) * 1981-12-18 1983-06-23 Konishiroku Photo Ind Co Ltd 電子写真感光体
JPS58123546A (ja) * 1982-01-19 1983-07-22 Ricoh Co Ltd 電子写真用複合感光体
JPS58125044A (ja) * 1982-01-21 1983-07-25 Ricoh Co Ltd 電子写真用複合感光体
JPS60254044A (ja) * 1984-05-30 1985-12-14 Toshiba Corp 電子写真感光体
JPS63205659A (ja) * 1987-02-20 1988-08-25 Hitachi Chem Co Ltd 電子写真感光体

Also Published As

Publication number Publication date
DE69011185D1 (de) 1994-09-08
KR900018749A (ko) 1990-12-22
EP0397146A3 (fr) 1991-04-24
KR960010180B1 (ko) 1996-07-26
EP0397146A2 (fr) 1990-11-14
CA2016257A1 (fr) 1990-11-09
CA2016257C (fr) 1995-09-05
DE69011185T2 (de) 1994-12-08

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