EP0450599A1 - Elektrophotographisches lichtempfindliches Material - Google Patents

Elektrophotographisches lichtempfindliches Material Download PDF

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Publication number
EP0450599A1
EP0450599A1 EP91105260A EP91105260A EP0450599A1 EP 0450599 A1 EP0450599 A1 EP 0450599A1 EP 91105260 A EP91105260 A EP 91105260A EP 91105260 A EP91105260 A EP 91105260A EP 0450599 A1 EP0450599 A1 EP 0450599A1
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EP
European Patent Office
Prior art keywords
phthalocyanine
photosensitive material
electrophotographic photosensitive
metallo
metal
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.)
Withdrawn
Application number
EP91105260A
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English (en)
French (fr)
Inventor
Tomohisa Gotoh
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.)
NEC Corp
Original Assignee
NEC Corp
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Filing date
Publication date
Application filed by NEC Corp filed Critical NEC Corp
Publication of EP0450599A1 publication Critical patent/EP0450599A1/de
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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
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/142—Inert intermediate layers

Definitions

  • the present invention relates to an electrophotographic photosensitive material, and more particularly to an electrophotographic photosensitive material which is improved in electric chargeability and sensitivity by using a specific compound as an undercoat layer of an electrophotographic photosensitive material layer.
  • an inorganic material such as selenium (Se), cadmium sulfide (CdS), zinc oxide (ZnO), amorphous silicon (a-Si) or the like is used. While those inorganic photo sensitive materials have many advantages, simultaneouly they have also various disadvantages, for example, they are harmful, expensive and so on. Therefore many organic photosensitive materials using organic substances without such disadvantages have recently been proposed and put to practical use.
  • a multilayer structure having a function separation type photosensitive material which includes, as separate layers, a material generating electric charge carriers (hereinafter called a charge generation material) and a material which receives the generated electric charge carriers and transports them (hereinafter called a charge transport material); and a single layer structure having a single layer type photosensitive material which executes generation of electric charge carriers and transportation of electric charge by means of the same material.
  • the multilayer structures are adopted more than the single layer structures because the formers have the larger range of selection of materials and have higher sensitivity than the latter.
  • an undercoat layer between an electrophotographic photosensitive material layer and a conductive substrate so that the retention factor of the charged potential of the electrophotographic photosensitive material layer can be increased.
  • the present invention is made in consideration of the foregoing conventional circumstances.
  • the object of the present invention is to provide an electrophotographic photosensitive material using an undercoating material which is excellent in the retention factor of the surface potential of the electrophotographic photosensitive material layer and in which the carrier injection is properly caused upon exposure.
  • the present invention provides an electrophotographic photosensitive material comprising an undercoat layer and an electrophotographic photosensitive material layer which are successively laminated on a surface of a conductive substrate, wherein said undercoat layer contains a high molecular substance which is represented by the general formula (1): (wherein m/n represents a real number equal to or larger than 0.1 and n is not zero).
  • a charge generation material which is contained in the electrophotographic photosensitive material layer, preferably includes, as the effective components, a composition crystal, which contains a total of not more than 50 parts by weight of one or more kinds from among metal-free aza-phthalocyanine porphyrin derivatives, metallo-aza-phthalocyanine porphyrin derivatives, metal-free phthalocyanine, metallo-phthalocyanine, metal-free naphthalocyanine or metallo-naphthalocyanine (wherein metal-free aza-phthalocyanine porphyrin derivatives, metallo-aza-phthalocyanine porphyrin derivatives, metal-free phthalocyanine and metallo-phthalocyanine may have a substitutional group in the benzene nucleous, and metal-free naphthalocyanine and metallo-naphthalocyanine may have a substitutional group in the naphtyl nucleous) and 100 parts by weight of titanyl phthalocyanine, and the above-
  • a partial N-methoxymethylated amide resin which is used for the undercoat layer according to the present invention, can be synthesized by reacting nylon-6 with formaldehyde and methanol.
  • the molecular weight of this resin is preferably 1,000 to 500,000.
  • crystallinity drops, and the melting point and the softening temperature also fall, in the amide resin.
  • the degree of substitution of methoxymethyl is about 30 %, the softening temperature becomes about 150 to 160 °C.
  • the resin in which the degree of substitution of methoxymethyl is of about 18 % to 60 % is preferred.
  • the partial N-methoxymethylated amide resin is soluble in aliphatic lower alcohol such as methyl alcohol, ethyl alcohol, N-propyl alcohol, isopropyl alcohol or the like, and aromatic alcohol such as phenol, cresol or the like. It is desirable to dissolve the resin in solvent by stirring for about one hour while heating.
  • the coating can be applied by the use of a coating method such as dip coating, spray coating, wire bar coating, blade coating, roller coating or the like. It is desired for the thickness of the undercoat layer to be about 0.1 to 2.0 ⁇ m.
  • the structure of the photosensitive material according to the present invention there is a structure in which an electrophotographic photosensitive material layer is functionally separated into a charge generation layer 3 and a charge transport layer 4, as shown in Fig. 1. And, as shown in Fig. 2, there may be also used a structure in which a charge generation material and a charge transport material are dispersed in a electrophotographic photosensitive material layer 5.
  • Each of such electrophotographic photosensitive material layers can be formed on a conductive substrate 1 through an undercoat layer 2.
  • the conductive substrate which is used in the present invention, there are used a plastic film provided with a metallic plate, a metallic drum or a metallic foil, which is respectively made of aluminum, nickel, chromium or the like; a plastic film provided with a thin layer made of tin oxide, indium oxide, chromium or the like; a sheet of paper or a plastic film to which a conductive material is coated or impregnated; or the like.
  • an inorganic material such as Se, CdS or the like which is a well-known photoconductive material, a phthalocyanine containing a metal atom such as Cu, Al, In, Ti, Pb, V or the like, or an organic material such as azo-pigment, his-azo pigment cyanine pigment or the like can be used either singularly or in combination thereof.
  • High sensitivity can be obtained, particularly when titanyl phthalocyanine composition crystal, which is shown in European Patent Application No. 90 11 0693.0, is used among them. The European Patent Application was filed on June 5, 1990 and was published on under No. .
  • the resin can be selected from among various kinds of insulation resins and can also be selected from organic photoconductive polymer such as poly-N-vinyl carbazole, polyvinyl anthracene, polyvinyl pyrene or the like.
  • organic photoconductive polymer such as poly-N-vinyl carbazole, polyvinyl anthracene, polyvinyl pyrene or the like.
  • phenol resin, urea resin, melamine resin, epoxy resin, silicon resin, vinyl chloride-vinyl acetate copolymer, butylal resin, xylene resin, urethane resin, acrylic resin, polycarbonate resin, polyacrylate resin, saturated polyester resin, phenoxy-resin or the like may be mentioned.
  • Solvents which dissolves those resins are different according to the kinds of the resins. It is desirable to select among the solvents mentioned later which do not dissolve the charge transport layer or the undercoat layer.
  • a ketone such as acetone, methyl ethyl keton, cyclohexane or the like; an amide such as N,N-dimethyl-formamide, N,N-dimethylacetoamide or the like; an ether such as tetrahydrofuran, dioxane, ethylene glycol monomethyl ether or the like; an ester such as methyl acetate, ethyl acetate or the like; an aliphatic hydrocarbon halogenide such as chloroform, methylene chrolide, dichloroethylene, carbon tetrachloride, trichlorethylene or the like; or an aromatic compound such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene or
  • the charge transport layer may be formed either by singularly using a charge transport material or by dissolving and dispersing a charge transport material in a binding resin.
  • a charge transport material any known charge transport agent of a hole transport type can be used.
  • the hole transport material pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N-phenylhydrazino-3-methlidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N,N-diphenylhydrazino-3-methylidene-10-ethylphenoxazine, a hydazone such as P-diethylaminobenzaldehyde-N,N-diphenylhydrazone, p-diethylaminobenzaldehyde-N-naphtyl-N-phenylhydrazone, 2-methyl-4-dibenzylaminobenzaldehyde-1'-ethyl-1'
  • the above mentioned charge transport material may be used either singularly or in combination of two or more kinds.
  • an insulating resin such as silicon resin, ketone resin, polymethyl methracrylate, polyvinyl chloride, acrylic resin, polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butylal, polyvinyl formal, polysulfone polyacrylamide, polyamide, chlorinated rubber of the like; poly-N-vinyl anthracene, polyvinyl pyrene or the like may be mentioned.
  • the coating may be applied by means of a method similar to that in the above-mentioned charge generation layer so that a film having a thickness of 5-50 ⁇ m preferably 10-20 ⁇ m may be formed after drying.
  • the electrophotographic photosensitive material according to the present invention can be applied not only to a laser beam printer, but also to other various optical memories using light sources in which the wavelength of the light emitted from semiconductor lasers, etc. is 750 to 850 nm.
  • Fig. 1 and Fig. 2 are partial sectional views of an embodiment of an electrophotographic photosensitive material according to the present invention, respectively.
  • an electrophotographic photosensitive material having a laminated type photosensitive layer has been obtained.
  • This photosensitive material was measured using an electrostatic copying paper testing apparatus (EPA-8100 manufactured by Kawaguchi Denki Seisakusho, Japan). Namely, the sample was electrified at a dark place by a corona discharge of -5.0 kV to be let alone, and the retention factor of the potential for 5 seconds (v5/v0) was measured (V0 is the initial surface potential and V5 is the surface potential after 5 seconds). Then, the sample was exposed to a white light of illuminance 5 lux., and the exposure quantity required for attenuating the surface potential to one half (E 1/2 lux ⁇ sec.) was determined. The results of the determination were indicated in Table 1.
  • An electrophotographic photosensitive material was obtained in a manner similar to that of Example 1 except that metal-free phthalocyanine was used as the charge generation substance, and the potential characteristics were examined. The results were indicated in Table 1.
  • An electrophotographic photosensitive material was manufactured in a manner similar to that of Example 1 except that triarylamine was used as the charge transport substance, and the potential characteristics were examined. The results were indicated in Table 1.
  • An electrophotographic photosensitive material was manufactured in a manner similar to that of Example 1 except that no undercoat layer was used, and the potential characteristics were examined. The results were indicated in Table 1.
  • An electrophotographic photosensitive material was manufactured in a manner similar to that of Example 1 except that a polycarbonate resin (Z-200 manufactured by Mitsubishi Gas Chemical Co. Japan) was used as the undercoat layer, and the potential characteristics were examined. The results were indicated in Table 1.
  • an electrophotographic photosensitive material which is excellent in the electric chargeability and has high sensitivity, is obtained by using a partial N-methoxymethylation polyamide resin as the undercoat layer of the electrophotographic photosensitive material layer.
  • an electrophotographic photosensitive material which is very superior in industrial fields, and used in optical printers such as laser beam printers, etc., is obtained.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP91105260A 1990-04-04 1991-04-03 Elektrophotographisches lichtempfindliches Material Withdrawn EP0450599A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP88294/90 1990-04-04
JP8829490A JPH03288157A (ja) 1990-04-04 1990-04-04 電子写真感光体

Publications (1)

Publication Number Publication Date
EP0450599A1 true EP0450599A1 (de) 1991-10-09

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EP91105260A Withdrawn EP0450599A1 (de) 1990-04-04 1991-04-03 Elektrophotographisches lichtempfindliches Material

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EP (1) EP0450599A1 (de)
JP (1) JPH03288157A (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3055351B2 (ja) * 1993-04-02 2000-06-26 富士電機株式会社 電子写真感光体
JPH08209023A (ja) * 1994-11-24 1996-08-13 Fuji Electric Co Ltd チタニルオキシフタロシアニン結晶とその製法及び電子写真感光体
US5874570A (en) * 1995-11-10 1999-02-23 Fuji Electric Co., Ltd. Titanyloxyphthalocyanine crystals, and method of preparing the same
JP2006078614A (ja) 2004-09-08 2006-03-23 Ricoh Co Ltd 電子写真感光体中間層用塗工液、それを用いた電子写真感光体、画像形成装置及び画像形成装置用プロセスカートリッジ
JP4541177B2 (ja) * 2005-02-16 2010-09-08 株式会社リコー 画像形成装置
JP4530874B2 (ja) * 2005-02-21 2010-08-25 株式会社リコー 画像形成装置
JP4541932B2 (ja) * 2005-03-08 2010-09-08 株式会社リコー 画像形成方法、画像形成装置及びプロセスカートリッジ
JP4541195B2 (ja) * 2005-03-14 2010-09-08 株式会社リコー 画像形成装置
JP4554408B2 (ja) * 2005-03-17 2010-09-29 株式会社リコー 画像形成装置
JP4549208B2 (ja) * 2005-03-17 2010-09-22 株式会社リコー 画像形成装置
JP4554409B2 (ja) * 2005-03-17 2010-09-29 株式会社リコー 画像形成装置
TWI453552B (zh) 2008-12-16 2014-09-21 Fuji Electric Co Ltd An electrophotographic photoreceptor, a manufacturing method thereof, and an electrophotographic apparatus

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4495263A (en) * 1983-06-30 1985-01-22 Eastman Kodak Company Electrophotographic elements containing polyamide interlayers
DE3716975A1 (de) * 1986-05-20 1987-11-26 Ricoh Kk Elektrophotographischer photoleiter
EP0378153A2 (de) * 1989-01-09 1990-07-18 Konica Corporation Elektrophotographischer Photorezeptor
FR2642189A1 (fr) * 1989-01-21 1990-07-27 Canon Kk Support electrophotographique photosensible

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4495263A (en) * 1983-06-30 1985-01-22 Eastman Kodak Company Electrophotographic elements containing polyamide interlayers
DE3716975A1 (de) * 1986-05-20 1987-11-26 Ricoh Kk Elektrophotographischer photoleiter
EP0378153A2 (de) * 1989-01-09 1990-07-18 Konica Corporation Elektrophotographischer Photorezeptor
FR2642189A1 (fr) * 1989-01-21 1990-07-27 Canon Kk Support electrophotographique photosensible

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPIL, no. 83-709070, Derwent; & JP-A-58 095 744 (CANON K.K.) 07 June 1983, whole abstract *
DATABASE WPIL, no. 91-121970, Derwent; & JP-A-03 062 041 (CANON K.K.) 18 March 1991, whole abstract. *
PATENT ABSTRACTS OF JAPAN, vol. 7, no. 196 (P-219)[1341] 26 August 1983; & JP-A-58 095 351 (CANON K.K.) 06 June 1983. *

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JPH03288157A (ja) 1991-12-18

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