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 or 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
  • G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom

Definitions

• the invention relates to an electrophotographic recording material consisting of an electrically conductive carrier material and a photoconductive double layer made of organic materials, as well as a method for producing these electrophotographic recording materials and their use for reprographic purposes.
• the surface of an electrophotographic element which contains a photo-semiconducting layer is first uniformly charged electrostatically for image formation.
• the photo semiconductor layer becomes electrically conductive on the irradiated surfaces, as a result of which the electrostatic surface charge flows off at these points if the electrically conductive carrier material is grounded.
• the unexposed areas retain their surface charge, so that a charge image corresponding to the original remains after the exposure.
• this charge image is treated with fine pigment pigment particles which have previously been charged in the opposite way to the surface charge of the electrophotographic element, these color pigment particles are deposited in the unexposed areas of the electrophotographic element and thus develop the invisible charge image into a visible image of the original.
• the image created in this way is then transferred to another surface, for example on paper, and fixed on it.
• the electrophotographic element can either be composed of a homogeneous layer of a photo semiconductor on an electrically conductive carrier material or of several layers arranged one above the other on the carrier.
• DE-OS 22 20 408 discloses materials of this type consisting of a conductive carrier, a first layer which contains charge carrier-producing compounds and a second layer with charge carrier transporting substances which is arranged in addition.
• Another group of charge-generating photoconductive organic materials is dispersed in the form of pigment particles in a matrix binder and applied to a support in a layer which contains the individual photoconductive particles.
• These are the electrophotographic elements described in the literature, which contain monoazo, disazo and squaric acid dye derivatives as coloring materials (e.g. US Pat. No. 3,775,105, US Pat. No. 3,824,099, US Pat. No. 3,898,084).
• the object of the invention was therefore to create extremely light-sensitive electrophotographic layers by means of organic photo semiconductors, which can be produced as simply as possible from a dye dispersion.
• the electrophotographic element should continue to be flexible, elastic and abrasion-resistant, the surface of which should be smooth and free of scoring, if possible without aftertreatment.
• the invention accordingly relates to dyes which are active in the first layer of the electrophotographic recording material as components which generate charge carriers.
• Dyes of the general formula I are suitable for this in which R 1 to R 4 are hydrogen, halogen, methyl and / or phenylthio, one or two of the radicals R 1 to R 4 are C 2 -C 6 -alkyl, cyclohexyl, phenyl, 2-naphthyl, hydroxy, C - to C 6 -alkoxy allyloxy, phenoxy, methylthio, benzylthio, C - to C 4 - alkylsulfonyl phenoxysulfonyl, trimethylsilyl, trifluoromethyl, cyano, nitro, amino, N, NC - to C 4 -dialkylamino, a radical of the formula a radical of the formula NH.CO.R 5 , where R 5 is C 1 to C 6 alkyl
• R 7 and R 8 which may be the same or different, are C 1 -C 4 -alkyl, cyclohexyl or phenyl or R and R together represent a tetramethylene group, an aromatic heterocyclic or heterocyclically saturated 5- or 6-ring and X , Y and Z have the meaning given above, and, compounds of the formulas III, IV and V in which X, Y and Z have the meaning given above.
• R 9 and R 10 which may be the same or different, cyano, nitro, 4-halophenyl, 4-cyanophenyl, 4-nitrophenyl, C 1 - to C 8 -alkoxycarbonyl, phenoxycarbonyl, a radical of the formula -CONH-R 11 , in which R 11 is hydrogen, C 1 - to C 9 -alkyl or a phenyl optionally substituted by phenoxy, cyano, nitro or CF 3 , up to three halogen, C 1 - to C 4 -alkyl or for the rest one.
• heterocyclic amine Sulfamoyl; Phenylsulfonyl with up to three halogens and / or C 1 - to C 4 -alkyl in the phenyl nucleus; a remainder of the formula in which A represents -0-, -S- or ⁇ NR, R represents hydrogen or C 1 - to C 4 -alkyl and R 12 and R 13 represents hydrogen or halogen, C 1 - to C 4 -alkyl or C 1 - are C 4 alkoxy; 1H-Naphth-2,3-d-imidazolyl, pyridyl, 4-thiazolyl, 2-methyl-4-thiazolyl, 2-phenyl-1,3,4-thiadiazolyl- (5), 2-quinolinyl, 3-indolyl or 3-benzothiazolyl.
• R 14 and R 15 which may be the same or different, cyano, methylcarbonyl, phenylcarbonyl, 4-nitrophenyl, 4-cyanophenyl, C 1 - to C6-alkoxycarbonyl, phenoxycarbonyl, phenylsulfonyl, a radical of the formula in which A , R 12 and R 13 have the meaning given above.
• R 16 and R 17 which may be the same or different, cyano, 4-nitrophenyl, 4-cyanophenyl, C 1 - to C 4 -alkoxycarbonyl, phenylsulfonyl, a radical of the formula in which R 12 and R 13 are hydrogen or halogen, C 1 - to C 4 -alkyl or C 1 - to C 4 -alkoxy and R 19 is hydrogen or C 1 - to C 4 -alkyl; 1H-Naphth-2,3-d-imidazolyl, pyridyl, 4-thiazolyl, 2-methyl-4-thiazolyl, 2-phenyl-1,3,4-thiadiazolyl- (5), 2-quinolinyl, 3-indolyl or 3-benzothiazolyl.
• R 9 has the meaning given above and R 6 'represents the residue of an aromatic or heterocyclic amine or hydrazine.
• R 14 has the meaning given above and R 18 phenyl, p- t olyl, 2- or 4-anisidyl, 2- or 4-chlorophenyl, 4-carbethoxyphenyl, 2-oxazolyl, 2-thiazolyl, 2- Imidazolyl, 2- (4-phenylthiazclyl), 2- (4-methyl-5-carboethoxythiazolyl), 2-benzthiazolyl.
• 2- (6-Ethoxybenzthiazolyl) 2-benzimidazolyl, 2- (1-methylbenzimidazolyl), 2- (5 - phenyl-1,3,4-thiadiazolyl) or 3-indazolyl.
• the first charge carrier-producing layer is applied to the electrically conductive layer carrier in the form of a dispersion.
• the dispersion for the first layer is produced by rolling together about 20 to 85 percent by weight of the solids content of the dispersion in one or more of the dyes suitable according to the invention and 80 to 15 percent by weight in a binder which is customary for this purpose and which may have barrier properties, in the form of a Solution in an organic, easily evaporable solvent.
• the first layer is cast in a thickness of approximately 0.005 to 5 / ⁇ m, preferably 0.05 to 2.0 / ⁇ m, which is to be understood as the solid layer thickness.
• An adhesive layer with a thickness of about 0.05 to 5 / ⁇ m, preferably 0.1 to 0.8 / ⁇ m, can be arranged between the carrier and the first layer.
• the transparent second layer is also arranged over the first layer by casting from a solution.
• the thickness of the second layer is preferably between 2 and 40 / um. It consists of 30 to 60 percent by weight, one or more charge carrier transporting compounds, 65 to 35 percent by weight of one or more binders customary for this, 0.1 to 4 percent by weight of additives that improve the mechanical properties and optionally up to 5 percent by weight of sensitizing or activating connections together.
• the casting process is carried out from a low-boiling solvent.
• a barrier layer of about 0.05 to 1.5 / ⁇ m, preferably 0.1 to 0.5 / ⁇ m is optionally arranged between the first and the second layer, while depending on the intended use of the electrophotographic recording material it may be appropriate to use a To apply the top and protective layer acting inactive layer on the charge transport layer.
• Aluminum foils, aluminum foils, nickel foils or plastic foils coated with aluminum, tin, lead, bismuth or similar metals, preferably polyester foils, are suitable as the electrically conductive carrier material. The selection is determined by the area of application of the electrophotographic element.
• the barrier layers between the conductive substrate and the first layer or between the same and the second layer usually consist of metal oxide layers, e.g. Alumina layers, polymers such as e.g. Polyamide, polyvinyl alcohol, polyacrylates, polystyrene or similar systems.
• the binder of the first layer can also serve as a barrier layer material at the same time.

Landscapes

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

Applications Claiming Priority (2)

Publications (2)

Family

ID=6127837

Family Applications (1)

Country Status (5)

Cited By (7)

Families Citing this family (3)

Citations (5)

Family Cites Families (12)

• 1981
  • 1981-03-20 DE DE19813110953 patent/DE3110953A1/de not_active Withdrawn
• 1982
  • 1982-03-12 EP EP82102008A patent/EP0061094B1/fr not_active Expired
  • 1982-03-12 DE DE8282102008T patent/DE3266612D1/de not_active Expired
  • 1982-03-19 JP JP57043024A patent/JPS57181552A/ja active Granted
  • 1982-03-19 DK DK123882A patent/DK162126C/da not_active IP Right Cessation
• 1983
  • 1983-11-22 US US06/554,435 patent/US4481272A/en not_active Expired - Lifetime

Patent Citations (6)

Also Published As

Similar Documents

Legal Events