EP0567395A2 - Elément photosensible électrophotographique, ainsi qu'un appareil électrophotographique et une unité de dispositif l'utilisant - Google Patents

Elément photosensible électrophotographique, ainsi qu'un appareil électrophotographique et une unité de dispositif l'utilisant Download PDF

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Publication number
EP0567395A2
EP0567395A2 EP93401029A EP93401029A EP0567395A2 EP 0567395 A2 EP0567395 A2 EP 0567395A2 EP 93401029 A EP93401029 A EP 93401029A EP 93401029 A EP93401029 A EP 93401029A EP 0567395 A2 EP0567395 A2 EP 0567395A2
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EP
European Patent Office
Prior art keywords
photosensitive member
charge
electrophotographic photosensitive
electrophotographic
layer
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Withdrawn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
EP93401029A
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German (de)
English (en)
Other versions
EP0567395A3 (fr
Inventor
Akihiro C/O Canon Kabushiki Kaisha Senoo
Toshihiro C/O Canon Kabushiki Kaisha Kikuchi
Tetsuro C/O Canon Kabushiki Kaisha Kanemaru
Takazaku Tanaka
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Canon Inc
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Canon Inc
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Filing date
Publication date
Application filed by Canon Inc filed Critical Canon Inc
Publication of EP0567395A2 publication Critical patent/EP0567395A2/fr
Publication of EP0567395A3 publication Critical patent/EP0567395A3/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
    • 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
    • G03G5/0675—Azo dyes
    • G03G5/0679—Disazo dyes
    • 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine

Definitions

  • the present invention relates to an electrophotographic photosensitive member. More particularly, the present invention relates to an electrophotographic photosensitive member comprising a photosensitive layer containing a triphenylamine of a specified structure. The present invention further relates to an electrophotographic apparatus and a device unit employing the above electrophotographic photosensitive member.
  • photosensitive members having an inorganic photosensitive layer mainly composed of zinc oxide, cadmium etc.
  • Such conventional photosensitive members satisfy the requirement for properties to some extent, but have disadvantages such as poor film-forming ability, insufficient plasticity, and high production cost.
  • the inorganic photoconductive materials are generally highly toxic, restricting the production process and handling of the materials.
  • organic photosensitive members having a photosensitive layer mainly composed of an organic photoconductive compound have many advantages over the inorganic photosensitive material, and are attracting attentions in recent years. Many organic photosensitive members have been proposed, and some are practically used.
  • organic photosensitive members there proposed those containing a photoconductive polymer such as poly-N-vinylcarbazole and a charge transfer complex formed from a Lewis acid such as 2,4,7-trinitro-9-fluorenone as main components.
  • a photoconductive polymer such as poly-N-vinylcarbazole
  • a charge transfer complex formed from a Lewis acid such as 2,4,7-trinitro-9-fluorenone
  • Known charge-generating substances include azo pigments, polycyclic quinone pigments, cyanine dyes, squaric acid dyes, and pyrylium dyes.
  • azo pigments of various structures are disclosed because of their high light-fastness and high charge-generating ability, and relatively easy synthesis.
  • charge-transporting substances include pyrazolines disclosed in Japanese Patent Publication No. 52-4188; hydrazones disclosed in Japanese Patent Publication No. 55-42380 and Japanese Laid-Open Patent No. 55-52063; triphenylamines disclosed in Japanese Patent Publication No. 58-32372 and Japanese Laid-Open Patent No. 61-132955; stilbenes disclosed in Japanese Laid-Open Patent Nos. 54-151955 and 58-198043, and the like.
  • the characteristics required for charge-transporting substance (1) stability to light and heat, (2) stability to ozone, NOx, and nitric acid generated by corona discharge, (3) high charge-transporting performance, (4) high compatibility with organic solvents and binders, and (5) easy production and low cost.
  • the present invention intends to provides an electrophotographic photosensitive member having a photosensitive layer containing a charge-transporting substance having a novel structure.
  • the present invention also intends to provide an electrophotographic photosensitive member having high sensitivity and stable potential characteristics even when repeatedly used.
  • the present invention further intends to provide an electrophotographic apparatus and an apparatus unit having the above electrophotographic photosensitive member.
  • the electrophotographic photosensitive member according to the present invention comprises an electroconductive support and a photosensitive layer formed thereon, the photosensitive layer containing a triphenylamine represented by the formula (1) below: wherein R , R 2 , and R 3 independently represent a hydrogen atom or an alkyl group of 1 to 3 carbons, and at least one of R 1 , R 2 , and R 3 is ethyl or propyl.
  • the electrophotographic apparatus and the device unit according to the present invention have the aforementioned electrophotographic photosensitive member.
  • the electrophotographic photosensitive member of the present invention has a photosensitive layer containing a triphenylamine represented by the formula (1) below: wherein R , R 2 , and R 3 independently represent a hydrogen atom or an alkyl group of 1 to 3 carbons, and at least one of R 1 , R 2 , and R 3 is ethyl or propyl.
  • R , R 2 , and R 3 independently represent a hydrogen atom or an alkyl group of 1 to 3 carbons, and at least one of R 1 , R 2 , and R 3 is ethyl or propyl.
  • the photosensitive layer of the present invention may have such construction as:
  • the compound of the present invention represented by Formula (1) has high transporting ability for positive holes, and is useful as a charge-transporting substance in the photosensitive layer of the above construction.
  • the primary charging polarity is preferably negative in the construction (1), preferably positive in the construction (2), and either positive or negative in the construction (3) of the photosensitive layer.
  • the electrophotographic photosensitive member of the present invention may have a protection layer on the surface of the photosensitive layer, or a subbing layer between the photosensitive layer and the electroconductive support in order to improve durability or adhesiveness, or to control charge injection.
  • the construction of the photosensitive member is not limited to those mentioned above.
  • the construction (1) is particularly preferred in the present invention. It is explained in more detail.
  • the electroconductive support in the present invention includes those shown below:
  • the charge-generating substance which may be used in the present invention includes substances shown below. Such charge-generating substances may be used singly or in combination of two or more thereof.
  • the layer containing a charge-generating substance namely a charge-generating layer is formed by dispersing a charge-generating substance as above in a suitable binder and applying the resulting dispersion on an electroconductive support, or otherwise by forming a thin film of a charge-generating substance on an electroconductive support by a dry process such as vapor deposition, sputtering, or CVD.
  • the aforementioned binder may be selected from a variety of binding resins such as polycarbonate resins, polyester resins, polyarylate resins, butyral resins, polystyrene resins, polyvinylacetal resins, diallyl phthalate resins, acrylic resins, methacrylic resins, vinyl acetate resins, phenol resins, silicone resins, polysulfone resins, styrene-butadiene copolymer resins, alkid resins, epoxy resins, urea resins, and vinyl chloride-vinyl acetate copolymer resins, but is not limited thereto.
  • the above resins may be used singly or in combination of two or more thereof.
  • the binder resin in the charge-generating layer is in an amount of preferably not more than 80 %, more preferably not more than 40 % by weight based on the total weight of the charge-generating layer.
  • the thickness of the charge-generating layer is preferably not more than 5 f..lm, more preferably from 0.01 f..lm to 2 ⁇ m.
  • a sensitizing agent may be added to the charge-generating layer.
  • the layer containing a charge-transporting substance may be formed from combination of at least one triphenylamine represented by Formula (1) and a suitable binder resin.
  • the binder resin employed for the charge-transporting layer includes those mentioned above for the charge-generating layer and additionally photoconductive polymers such as polyvinylcarbazoles and polyvinylanthra- cenes.
  • the binder resin and the triphenylamine of the present invention are blended in a ratio of from 10 to 500 parts by weight to 100 parts by weight of the binder resin.
  • the charge-transporting layer is connected electrically to the charge-generating layer, and has function of receiving the charge carriers generated in the charge-generating layer and transporting the charge carriers to the surface of the photosensitive member. Since the ability of the charge-transporting layer in transporting the charge carriers has limitation, the layer should not be unnecessarily thick, and is preferably in the range of from 5 ⁇ m to 40 ⁇ m, more preferably from 10 ⁇ m to 30 ⁇ m.
  • the charge-transporting layer may further contain an antioxidant, a UV-absorber, a plasticizer, or a known charge-transporting substance.
  • the above-described layers may be formed by a coating process such as dip coating, spray coating, spinner coating, roller coating, Meyer bar coating or blade coating using a suitable organic solvent.
  • the electrophotographic photosensitive member of the present invention is useful not only for electrophotographic copying machines, but also for a variety of electrophotography application fields, such as laser beam printers, CRT printers, LED printers, facsimile machines, and electrophotographic engraving systems.
  • Fig. 1 illustrates schematically an example of the constitution of a transfer type electrophotographic apparatus employing an electrophotographic photosensitive member of the present invention.
  • a drum type photosensitive member 1 as an image holding member is driven to rotate around the axis 1a in the arrow direction at a prescribed peripheral speed.
  • the photosensitive member 1 is uniformly charged positively or negatively at the peripheral face by an electrostatic charging means 2 during rotation, and then exposed to image-exposure light L (e.g., slit exposure, laser beam-scanning exposure, etc.) at the exposure part 3 with an image-exposure means (not shown in the drawing), whereby an electrostatic latent image is sequentially formed on the peripheral surface in accordance with the exposed image.
  • image-exposure light L e.g., slit exposure, laser beam-scanning exposure, etc.
  • the electrostatic latent image is developed with a toner by a developing means 4.
  • the developed toner image is successively transferred by a transfer means 5 onto a surface of a transfer-receiving material P which is fed from a transfer-receiving material feeder not shown in the drawing, between the photosensitive member 1 and the transfer means 5 synchronistically with the rotation of the photosensitive member 1.
  • the transfer-receiving material P which has received the transferred image is separated from the photosensitive member surface, and introduced to an image fixing means 8 for fixation of the image and sent out from the copying machine as a duplicate copy.
  • the surface of the photosensitive member 1, after the image transfer, is cleaned with a cleaning means 6 to remove any remaining un-transferred toner, and is treated for charge elimination with a pre-exposure means 7 for repeated use for image formation.
  • the generally employed charging means 2 for uniformly charging the photosensitive member 1 is a corona charging apparatus.
  • the generally employed transfer means 5 is also a corona charging means.
  • two or more of the constitutional elements, the above described photosensitive member, the developing means, the cleaning means, etc. may be integrated into one device unit, which may be made removable from the main body of the apparatus.
  • at least one of the charging means, the developing means, and the cleaning means is combined with the photosensitive member 1 into one device unit which is removable from the main body of the apparatus by aid of a guiding means such as rails of the main body of the apparatus.
  • the image exposure light L projected onto the photosensitive member may be reflected light or transmitted light from an original copy, or otherwise the information is read out by a sensor from an original and signalized, and the exposure light is projected onto a photosensitive member, by scanning with a laser beam, driving an LED array, or driving a liquid crystal shutter array according to the signal.
  • Fig. 2 is a block diagram of an example of this case.
  • a controller 11 controls the image-reading part 10 and a printer 19. The entire of the controller 11 is controlled by a CPU 17. Readout data from the image reading part 10 are transmitted through a transmitting circuit 13 to the other communication station. Data received from the other communication station are transmitted through a receiving circuit 12 to a printer 19. The image data are stored in an image memory 16. A printer controller 18 controls a printer 19. The numeral 14 denotes a telephone set.
  • the images are recorded in such a manner that the CPU 17 reads out one page of the image information, and sends out the one page of the decoded information to the printer controller 18, which controls the printer 19 on receiving the one page of the information from CPU 17 to record the image information.
  • the CPU 17 receives the subsequent page of information.
  • a coating liquid for a charge-generating layer was prepared by dispersing 1.0 g of the azo pigment represented by the formula below in a solution of 0.5 g of a butyral resin (butyralation degree of 80 mol%) in 60 ml of tetrahydrofuran by means of a sand mill for 48 hours.
  • This coating liquid was applied on an aluminum sheet with a Meyer bar to obtain a charge-generating layer of 0.2 ⁇ m in dry thickness.
  • the resulting electrophotographic photosensitive member was tested for charging characteristics by subjecting it to static corona charging with an electrostatic copying paper tester (Model-SP-428 made by Kawagichi Denki K.K.) at -5 KV, keeping it in the dark for one second, and exposing it to the light of 20 lux.
  • an electrostatic copying paper tester Model-SP-428 made by Kawagichi Denki K.K.
  • the measured charging characteristics were the surface potential (V o ) immediately after the charging, the surface potential (V i ) after the one-second dark decay, and the E 1/5 exposure light which decreases the surface potential from V 1 to (1/5)V , corresponding to sensitivity.
  • Electrophotographic photosensitive members were prepared and evaluated in the same manner as in Example 1 except that Exemplified Compound No. 1 as the charge-transporting substance was replaced respectively with Exemplified Compounds Nos. 2, 3, 4, 5, 7, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 22, 23, and 24. The results are shown in Table 2.
  • Electrophotographic photosensitive members were prepared and evaluated in the same manner as in Example 1 except that Exemplified Compound No. 1 as the charge-transporting substance was replaced respectively with Comparative Compounds Nos. 1 to 4. The results are shown in Table 3.
  • electrophotographic photosensitive members of the present invention are superior to those using the Comparative Compound in the sensitivity and the potential stability on repeated use.
  • oxytitanium phthalocyanine 1.0 Gram of oxytitanium phthalocyanine was dispersed in a solution of 0.4 g of a phenoxy resin in 100 g of cyclohexanone by means of a ball mill for 40 hours. The resulting dispersion was applied on an aluminum sheet with a Meyer bar and was dried at 80°C for 0.5 hour to obtain a charge-generating layer of 0.15 ⁇ m thick.
  • the obtained electrophotographic photosensitive member was subjected to corona discharge of -5 KV.
  • the measured charging characteristics were the surface potential (V o ) immediately after the charging, the surface potential (V i ) after the dark decay for one second, and the E 1/6 exposure light, namely the sensitivity, which decreases the surface potential from V 1 to (1/6)V .
  • the light source was a gallium/alumi- num/arsine ternary semiconductor laser (power: 5 mW, wavelength: 780 nm). The results are as shown below. V 0 : -710 (V), V 1 : -705 (V) E 1/6 : 0.25 ( ⁇ J/cm2)
  • An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 21 except that Exemplified Compound No. 13 was used as the charge-transporting substance in place of the Exemplified Compound No. 1.
  • the charging characteristics were excellent as below, and the printed images of excellent quality were obtained from the beginning of the test to 3000th sheet of printing.
  • V o -720 (V), V 1 : -715 (V)
  • E 1/6 0. 25 ( ⁇ J/cm 2 )
  • a 2% solution of alcohol-soluble nylon (6-66-610-12 quaternary nylon copolymer) in methanol was applied on an aluminum sheet to form a subbing layer of 0.5 ⁇ m in dry thickness.
  • 0.5 g of the azo pigment represented by the formula below was dispersed in 10 ml of tetrahydrofuran by means of a sand mill.
  • the resulting dispersion was applied on the subbing layer prepared above with a Meyer bar so as to obtain a dry thickness of 18 ⁇ m.
  • An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 23 except that Exemplified Compound No. 13 was used as the charge-transporting substance in place of the Exemplified Compound No. 1. The results were as below. V 0 : -700 (V), V 1 : -690 (V) E 1/6 : 0.64 ( ⁇ J/cm 2 )
  • the electrophotographic photosensitive member having a photosensitive layer containing the triphenylamine of the present invention has high sensitivity, causing less change of light-area potential and dark-area potential in continuous image formation, and having excellent durability.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP9393401029A 1992-04-23 1993-04-21 Elément photosensible électrophotographique, ainsi qu'un appareil électrophotographique et une unité de dispositif l'utilisant. Withdrawn EP0567395A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP12942492 1992-04-23
JP129424/92 1992-04-23

Publications (2)

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EP0567395A2 true EP0567395A2 (fr) 1993-10-27
EP0567395A3 EP0567395A3 (fr) 1994-10-19

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EP9393401029A Withdrawn EP0567395A3 (fr) 1992-04-23 1993-04-21 Elément photosensible électrophotographique, ainsi qu'un appareil électrophotographique et une unité de dispositif l'utilisant.

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101770185A (zh) * 2010-02-05 2010-07-07 上海宏力半导体制造有限公司 一种可减少缺陷的显影方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63155053A (ja) * 1986-12-18 1988-06-28 Alps Electric Co Ltd 電子写真用有機光導電材料
EP0409737A1 (fr) * 1989-07-21 1991-01-23 Canon Kabushiki Kaisha Phtalocyanine d'oxytitane, son procédé de fabrication et élément électrophotoconducteur l'utilisant
US4999268A (en) * 1988-02-10 1991-03-12 Fuji Xerox Co., Ltd. Function separated electrophotographic photoreceptor containing selenium

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63155053A (ja) * 1986-12-18 1988-06-28 Alps Electric Co Ltd 電子写真用有機光導電材料
US4999268A (en) * 1988-02-10 1991-03-12 Fuji Xerox Co., Ltd. Function separated electrophotographic photoreceptor containing selenium
EP0409737A1 (fr) * 1989-07-21 1991-01-23 Canon Kabushiki Kaisha Phtalocyanine d'oxytitane, son procédé de fabrication et élément électrophotoconducteur l'utilisant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 12, no. 417 (P-782) (3264) 7 November 1988 & JP-A-63 155 053 (ALPS ELECTRIC CO., LTD.) 28 June 1988 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101770185A (zh) * 2010-02-05 2010-07-07 上海宏力半导体制造有限公司 一种可减少缺陷的显影方法

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EP0567395A3 (fr) 1994-10-19

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