US3867140A - Organic photoconductor-(mononitro-2-aza-fluorenylidene)malononitrile charge transfer complex - Google Patents
Organic photoconductor-(mononitro-2-aza-fluorenylidene)malononitrile charge transfer complex Download PDFInfo
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- US3867140A US3867140A US326563A US32656373A US3867140A US 3867140 A US3867140 A US 3867140A US 326563 A US326563 A US 326563A US 32656373 A US32656373 A US 32656373A US 3867140 A US3867140 A US 3867140A
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- United States
- Prior art keywords
- malononitrile
- aza
- fluorenylidene
- mononitro
- charge transfer
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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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
Definitions
- ABSTRACT Photosensitive material for use in electrophotography which is a charge transfer complex comprising (mononitro-2-aza-9-fluoreny1idene) malononitrile and an organic photoconductor.
- the present invention relates to novel compositions suitable for use in electrophotography.
- Electrophotography is an art which usefully combines photoconductivity with electrostatic phenomena.
- a wide variety of inorganic substances as selenium, zinc oride, and the like have heretofore been employed as photoconductors.
- organic photoconductive substances such as poly-N-vinyl carbazole and others have attracted wide attention. They are of particular interest because of their advantageous properties with respect to cost of production, transparency of product film, ease of film forming, etc.
- their wide adoption has been impeded because they are generally inferior to inorganic substances in sensitivity and exhibit only marginal sensitivities in the visible region of the spectra. This problem has been somewhat alleviated by the use of various sensitizing substances.
- Another problem which has retarded the adoption of organic photoconductors is that it is difficult to preserve them.
- One object of the present invention is to provide organic photoconductive compositions which manifest useful sensitivity in the visible region of the spectrum.
- Another object of the present invention is to provide organic photoconductive compositions which are superior in film transparency, film formability, preservability, etc.
- a principal feature of the invention is the provision of a charge transfer complex comprising a novel (mononitro-Z-aza- 9-fluorenylidene) malononitrile electron acceptor and any known organic photoconductive electron donor.
- the above mentioned charge transfer complex comprising (mononitro-Z-aza-9-fluorenylidene) malononitrile as the acceptor and various organic, photoconductive donors comprise the photoconductive compositions of the present invention.
- the compositions display panchromatic sensitivity and are useful with actinic light in the visible region of the spectrum. Their utility can be enhanced however by the addition of known sensitizers such as Rhodamine B, Rose Bengal, fluorescein and the like.
- Preparation of electrophotographic compositions of the present invention can be easily effected by: mixing (mononitro-2-aza-9-fluorenylidene) malononitrile, the acceptor, with the selected donor in the weight ratio of from 1:100 to 1501100; adding such additives as may be desired such as binders, additional sensitizers and other conventional additives to the resulting mixture; dissolving the mixture in an appropriate inert, organic solvent such as dioxane, tetrahydrofuran, etc.; subsequently coating the thus obtained solution on an appropriate substrate.
- Suitable binders include, for example, novolak, acrylic resins and others of the type conventionally employed.
- Suitable substrates include, for example, aluminum plates, polyester films with a vacuum deposited aluminum layer, paper treated for conductivity, etc. The final product is dried.
- a composition of the invention may contain added binder in the range of about 5 to 50 parts by weight relative to the total weight of the mixture, and additional sensitizers such as fluorescein in the weight range of about 0.001 to 0.0] parts by weight based on the weight of the donor.
- additional sensitizers such as fluorescein in the weight range of about 0.001 to 0.0] parts by weight based on the weight of the donor.
- Typical donors which may be employed in this invention include condensation polycyclic compounds such as pyrene, perylene, anthracene, etc., phenothiazine,
- the (mononitro-2aza-9-fluorenylidene) malononitrile for use in the present invention can be synthesized by the following procedure:
- the photosensitive compositions of this invention comprising a charge transfer complex containing (mononitro-2-aza-9-fluorenylidene) malononitrile and an organic photoconductive donor as the principal components are sensitive in the visible region of the spectrum, have satisfactory preservability and reproducibility, and. are further applicable to the transfer process. When deposited on an electrically conductive substrate they form excellent electrophotographic plates.
- EXAMPLE 1 A solution obtained by dissolving 64 mg of poly-N- vinyl carbazole, 91 mg of (7-nitro-2-aza-9- fluorenylidene) malononitrile and 100mg of diphenyl chloride in 10 g of tetrahydrofuran is coated by means ofa doctor blade having wet gaps of 200p, on an aluminum coated Mylar film and dried to produce an electrophotographic plate having a photosensitive film layer about 10 microns thick.
- the thus prepared plate is charged by means of corona discharge (-6KV), exposed to light by means of an apparatus equipped with a tungsten lamp capable of producing an intensity ofillumination on the sensitive surface of the plate of 3 luxes and measured for its surface potential, whereby the time required for decreasing said potential to half (hereinafter referred to as exposure time required for half decay) is measured. It was found that the exposure time required for half decay is about 4 seconds.
- EXAMPLE 2 A solution is prepared by dissolving 900 mg of poly- N-viny1-3-bromocarbazole, 91 mg of (7-nitro-2-aza-9- fluorenylidene) malononitrile and mg of diphenyl chloride in 15 g of tetrahydrofuran. When this composition is treated in the same manner as the compositions of Example 1 it is found that the exposure time required for half decay is about 3.5 seconds.
- EXAMPLE 3 A sensitive material is prepared in the same way as in Example 1 except for increasing the amount of (7- nitro-2-aza-9-fluorenylidene) malononitrile to 910 mg from 91 mg as employed in Example 1. The exposure time required for half decay of this sensitive material is about 1.5 seconds.
- EXAMPLE 4 A sensitive material is prepared in the same way as in Example 2 except for increasing the amount of (7- nitro-2-aza-9-fluorenylidene) malononitrile to 910 mg from 91 mg as employed in Example l. The exposure time required for half decay of this sensitive material is about 1.4 seconds.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Photosensitive material for use in electrophotography which is a charge transfer complex comprising (mononitro-2-aza-9fluorenylidene) malononitrile and an organic photoconductor.
Description
ite J Hashimoto 1 Feb. 18, 1975 [54] ORGANIIC 3,484,237 12/1969 Shattuck e461 96/15 PHOTOCONDUCT0R (M0N0NITR0 2 3,485,625 12/1969 Fox..... 96/15 3,556,785 1/1971 Baltazz|.'...,..,.. 96/15 x 3,583,869 6/1971 T b k 1 1. 96 1.5
FLUORENYLIDENE)MALONONITRILE 3,595,648 7/1971 96/15 x CHARGE TRANSFER COMPLEX 3,674,473 7 1972 BlaflCl'lEItfi 96/15 3,677,752 7 1972 L k -1. 96 1.5 x
[75] Inventor Hashlmmo Tokyo Japan 3,752,668 8/1973 96/15 [73] Assignee: Kabushiki Kaisha Ricoh, Tokyo,
Japan [22] Filed: Jan. 24, 1973 [21] Appl. N0.: 326,563
[30] Foreign Application Priority Data Jan. 24, I972 Japan 479293 [52] US. Cl 96/l.5, 96/].6, 260/294.9, 260/297 R, 260/297 T, 252/501 [51] lint. Cl G03g 5/00 [58] Field Of Search 96/15, 1.6; 252/501 [56] References Cited UNITED STATES PATENTS 2,980,535 4/1961 Schroeter 96/1.5 X 3,244,516 4/1966 Neugebauer et a1 96/1.5 3,252,794 5/1966 Schaum et a1. 96/1.5 3,301,676 I/l967 Tomanek v 1 1 96/15 3,307,940 3/1967 Haegl et a1 1. 96/l.5'
3,796,572 3/1974 Hashimoto 96/15 OTHER PUBLICATIONS Wagner et al., A Study of the Relation of Electron Affinity to the Photoconductivity of Doped Poly-N- Vinylcarbazale Films: A New Method of Analyzing the Photoresponse, Photographic Science and Engineering, Vol. 14, No. 3, MayJune, 1970, pp. 205209.
Primary Examiner-Morman G. Torchin Assistant ExaminerJohn R. Miller Attorney, Agent, or FirmCooper, Dunham, Clark, Griffin & Moran [57] ABSTRACT Photosensitive material for use in electrophotography which is a charge transfer complex comprising (mononitro-2-aza-9-fluoreny1idene) malononitrile and an organic photoconductor.
1 Claim, 1 Drawing Figure 5, g H ETHEIZ CH3 Hun -11,90 11/ BACKGROUND OF THE INVENTION A. Field of the Invention The present invention relates to novel compositions suitable for use in electrophotography.
B. Description of the Prior Art Electrophotography is an art which usefully combines photoconductivity with electrostatic phenomena. A wide variety of inorganic substances as selenium, zinc oride, and the like have heretofore been employed as photoconductors. Recently, however, organic photoconductive substances such as poly-N-vinyl carbazole and others have attracted wide attention. They are of particular interest because of their advantageous properties with respect to cost of production, transparency of product film, ease of film forming, etc. Despite these advantages, their wide adoption has been impeded because they are generally inferior to inorganic substances in sensitivity and exhibit only marginal sensitivities in the visible region of the spectra. This problem has been somewhat alleviated by the use of various sensitizing substances. Another problem which has retarded the adoption of organic photoconductors is that it is difficult to preserve them.
SUMMARY OF THE INVENTION One object of the present invention is to provide organic photoconductive compositions which manifest useful sensitivity in the visible region of the spectrum.
Another object of the present invention is to provide organic photoconductive compositions which are superior in film transparency, film formability, preservability, etc. A principal feature of the invention is the provision of a charge transfer complex comprising a novel (mononitro-Z-aza- 9-fluorenylidene) malononitrile electron acceptor and any known organic photoconductive electron donor. 1
DETAILED DESCRIPTION OF THE INVENTION The above mentioned charge transfer complex comprising (mononitro-Z-aza-9-fluorenylidene) malononitrile as the acceptor and various organic, photoconductive donors comprise the photoconductive compositions of the present invention. The compositions display panchromatic sensitivity and are useful with actinic light in the visible region of the spectrum. Their utility can be enhanced however by the addition of known sensitizers such as Rhodamine B, Rose Bengal, fluorescein and the like.
Preparation of electrophotographic compositions of the present invention can be easily effected by: mixing (mononitro-2-aza-9-fluorenylidene) malononitrile, the acceptor, with the selected donor in the weight ratio of from 1:100 to 1501100; adding such additives as may be desired such as binders, additional sensitizers and other conventional additives to the resulting mixture; dissolving the mixture in an appropriate inert, organic solvent such as dioxane, tetrahydrofuran, etc.; subsequently coating the thus obtained solution on an appropriate substrate. Suitable binders include, for example, novolak, acrylic resins and others of the type conventionally employed. Suitable substrates include, for example, aluminum plates, polyester films with a vacuum deposited aluminum layer, paper treated for conductivity, etc. The final product is dried.
Typically, a composition of the invention may contain added binder in the range of about 5 to 50 parts by weight relative to the total weight of the mixture, and additional sensitizers such as fluorescein in the weight range of about 0.001 to 0.0] parts by weight based on the weight of the donor.
Typical donors which may be employed in this invention include condensation polycyclic compounds such as pyrene, perylene, anthracene, etc., phenothiazine,
phenoxazine, thionine, 9,9-diphenyl-9,10- dihydroanthracene, 2,3-diphenyl pyrrocoline, a,w-bis( N-carbazolyl )-propane, N ,N,N,N -tetrabenzyl-P-phenylene diamine, 1,6-dimethoxyphenazine, 1,8-bis(dimethylamino)-naphthalene, 1,1,5- triphenylbrom-1-en-4-in-3-ol,N-ethyl carbazole, N- propyl carbazole, 3,6-dibrom-N-ethyl carbazole, 2- phenyl-3-P-dimethylaminophenyl quinoxaline, acridine, p,p-bis-dimethylamino biphenyl, p,p'- bisdiphenylamino biphenyl, 2,3,4,5-tetrakis (p-dimethylaminophenyl )-pyrrole, 2-p-diimethylaminophenyl- 3,4-diphenyl imidazole, 2,5-lbis(p-dimethylaminophenyl)-l,3,4-oxadiazole, 4-phenyl-5-pdimethylaminophenyl-3H-2-imidazolone, etc., and, as high-molecular compounds, there may be poly-N-vinyl carbazole, poly-3-vinyl-N-ethyl carbazole, polyphenylene pyrazole, poly-l-allyl-4,5-diphenyl imidazole, polyvinyl pyrene, polyvinyl phertanthrene, polyacenaphthylene, poly-N-vinyl-3,6-dibromocarbazole, polyvinyl dibenzothiophene, poly-9-vinyl acridine, poly-N- allyl phenothiazine, poly-P-imidazolyl-(Z)-styrene, polyvinyl anthracene, poly-P-phenylene-l,3,-oxadiazole, anthracene-formalin condensation resin, polypylomeritimide, vinyl anthracene-N-vinyl carbazole copolymer, l,2dihydroacenaphthene-indene copolymer, pyrene-formalin condensate, polyvinyl Malachite Green, polyvinyl dibenzofuran, poly-Z-vinyl quinoline, poly-Z-vinyl furan, poly-3-benzofuran, poly-2-vinyl-4-(4'-dimethyl aminophenyl)-3-phenyl oxazole, as well as reaction products between polyvinyl amine and anthracene-9-aldehyde, naphthaleneformalin resins, N-ethyl carbazole-formalin resins, etc.
The (mononitro-2aza-9-fluorenylidene) malononitrile for use in the present invention can be synthesized by the following procedure:
First, by effecting Friedel Krafts reaction between hydrochloride nicotinic acid chloride and mesitylene in accordance with Reynold C. Fuson and John J. Millers method [cf.J.Am.Chem. Soc. 79.3477 (1957)],3- mesitol pyridine (yield: 63 percent, b.p.:l57.5158 C/4mml-Ig) is obtained.
Next, by phenylizing this reaction product through Grignard's reaction, 3-mesitol-4-phenyldihydropyridine (yield: 76 percent, m.p.:l83l85.5 C; light yellow powder) is obtained. Further, by oxidizing this product with chloranil in benzene, 3mesitol-4- phenyl pyridine is obtained.
When the thus obtained compound is subjected to ring formation by utilizing polyphosphoric acid, there is obtained 2-aza-9-fluorenone to serve as the material. Then by reacting this material with mixed sulfuric and nitric acids in an acetic acid solvent at a temperature of about C for lhour, mononitro-2-aza-9- fluorenone which is principally the 7-nitrated product is obtained.
Subsequently, by making this mononitro-Z-aza- 9fluorenone react with malononitrile in methanol in the presence of piperidine as catalyst, the intended (mononitro-2-aza-9-fluoreny1idene) malononitrile is obtained. The reactions are shown in FIG. 1.
The photosensitive compositions of this invention comprising a charge transfer complex containing (mononitro-2-aza-9-fluorenylidene) malononitrile and an organic photoconductive donor as the principal components are sensitive in the visible region of the spectrum, have satisfactory preservability and reproducibility, and. are further applicable to the transfer process. When deposited on an electrically conductive substrate they form excellent electrophotographic plates.
The following non-limiting examples are given by way of illustration only:
EXAMPLE 1 A solution obtained by dissolving 64 mg of poly-N- vinyl carbazole, 91 mg of (7-nitro-2-aza-9- fluorenylidene) malononitrile and 100mg of diphenyl chloride in 10 g of tetrahydrofuran is coated by means ofa doctor blade having wet gaps of 200p, on an aluminum coated Mylar film and dried to produce an electrophotographic plate having a photosensitive film layer about 10 microns thick.
Subsequently, the thus prepared plate is charged by means of corona discharge (-6KV), exposed to light by means of an apparatus equipped with a tungsten lamp capable of producing an intensity ofillumination on the sensitive surface of the plate of 3 luxes and measured for its surface potential, whereby the time required for decreasing said potential to half (hereinafter referred to as exposure time required for half decay) is measured. It was found that the exposure time required for half decay is about 4 seconds.
Similar results are obtained with poly-N-vinyl-3,6- dibromocarbazole and poly-N-vinyl-3 chlorocarbazole.
EXAMPLE 2 A solution is prepared by dissolving 900 mg of poly- N-viny1-3-bromocarbazole, 91 mg of (7-nitro-2-aza-9- fluorenylidene) malononitrile and mg of diphenyl chloride in 15 g of tetrahydrofuran. When this composition is treated in the same manner as the compositions of Example 1 it is found that the exposure time required for half decay is about 3.5 seconds.
EXAMPLE 3 A sensitive material is prepared in the same way as in Example 1 except for increasing the amount of (7- nitro-2-aza-9-fluorenylidene) malononitrile to 910 mg from 91 mg as employed in Example 1. The exposure time required for half decay of this sensitive material is about 1.5 seconds.
EXAMPLE 4 A sensitive material is prepared in the same way as in Example 2 except for increasing the amount of (7- nitro-2-aza-9-fluorenylidene) malononitrile to 910 mg from 91 mg as employed in Example l.The exposure time required for half decay of this sensitive material is about 1.4 seconds.
EXAMPLE 5 fluorenylidene) malononitrile.
Claims (1)
1. A PHOTOSENSITIVE MATERIAL FOR USE IN ELECTROPHOTOGRAPHY WHICH IS A CHARGE TRANSFER COMPLEX COMPRISING 100 PARTS BY WEIGHT OF AN ORGANIC PHOTOCONDUCTOR AND 1 TO 150 PARTS BY WEIGHT OF (MONONITRO-2-AZA-9-FLUORENYLIDENE) MALONONITRILE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/537,405 US3974167A (en) | 1972-01-24 | 1974-12-30 | (7-Nitro-2-aza-9-fluorenylidene) malononitrile |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP47009293A JPS4949506B2 (en) | 1972-01-24 | 1972-01-24 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/537,405 Division US3974167A (en) | 1972-01-24 | 1974-12-30 | (7-Nitro-2-aza-9-fluorenylidene) malononitrile |
Publications (1)
Publication Number | Publication Date |
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US3867140A true US3867140A (en) | 1975-02-18 |
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ID=11716414
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Application Number | Title | Priority Date | Filing Date |
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US326563A Expired - Lifetime US3867140A (en) | 1972-01-24 | 1973-01-24 | Organic photoconductor-(mononitro-2-aza-fluorenylidene)malononitrile charge transfer complex |
Country Status (5)
Country | Link |
---|---|
US (1) | US3867140A (en) |
JP (1) | JPS4949506B2 (en) |
DE (1) | DE2302625C3 (en) |
FR (1) | FR2169211B1 (en) |
GB (1) | GB1416232A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3974167A (en) * | 1972-01-24 | 1976-08-10 | Ricoh Co., Ltd. | (7-Nitro-2-aza-9-fluorenylidene) malononitrile |
US4056391A (en) * | 1975-09-22 | 1977-11-01 | Xerox Corporation | Method for enhancing solid solution stability of electron acceptor molecules and electrophotographic compositions |
US4063947A (en) * | 1975-10-29 | 1977-12-20 | Xerox Corporation | Photoconductive insulating films comprising fluorenone-substituted oligomers |
US4474865A (en) * | 1983-08-08 | 1984-10-02 | Xerox Corporation | Layered photoresponsive devices |
KR100457523B1 (en) * | 2002-06-07 | 2004-11-17 | 삼성전자주식회사 | Single layered electrophotographic photoreceptor |
CN104035294A (en) * | 2013-03-07 | 2014-09-10 | 佳能株式会社 | Electrophotographic photoreceptor, electrophotographic devoce, PROCESS CARTRIDGE, and fused polycyclic aromatic compounds |
US20140255836A1 (en) * | 2013-03-07 | 2014-09-11 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, and electrophotographic apparatus and process cartridge each including the electrophotographic photosensitive member |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2964000B1 (en) * | 2002-12-19 | 2022-10-05 | Signify Holding B.V. | Led driver |
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US2980535A (en) * | 1954-01-05 | 1961-04-18 | Feldmuhle Papier Und Zellstoff | Light sensitive layers of synthetic materials |
US3244516A (en) * | 1959-04-09 | 1966-04-05 | Azoplate Corp | Electrophotographic mateiral and process |
US3252794A (en) * | 1956-11-14 | 1966-05-24 | Agfa Ag | Photoconductive layers and process for electrophotography |
US3301676A (en) * | 1963-10-12 | 1967-01-31 | Azoplate Corp | Process and material for the production of electrophotographic images |
US3307940A (en) * | 1959-05-30 | 1967-03-07 | Azoplate Corp | Electrophotographic process employing photoconductive polymers |
US3484237A (en) * | 1966-06-13 | 1969-12-16 | Ibm | Organic photoconductive compositions and their use in electrophotographic processes |
US3485625A (en) * | 1966-06-09 | 1969-12-23 | Eastman Kodak Co | Photoconductive elements containing 2,3,4,5-tetraaryl pyrrole |
US3556785A (en) * | 1968-02-23 | 1971-01-19 | Addressograph Multigraph | Sensitizers for organic photoconductor comprising orazolone and butenolide derivatives of of fluorenone |
US3583869A (en) * | 1967-03-24 | 1971-06-08 | Ricoh Kk | Electrophotographic copying paper containing poly-n-vinyl-3-azo carbazole |
US3595648A (en) * | 1967-03-23 | 1971-07-27 | Ricoh Kk | Poly-n-vinyl-3-nitro carbazole photoconductive material |
US3674473A (en) * | 1970-10-06 | 1972-07-04 | Addressograph Multigraph | Cumulene containing photoconductive binder elements for use in electrophotography |
US3677752A (en) * | 1969-09-02 | 1972-07-18 | Eastman Kodak Co | Bis(dialkylaminoaryl)ethylene photoconductors |
US3752668A (en) * | 1967-10-30 | 1973-08-14 | Addressograph Multigraph | Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers |
US3796572A (en) * | 1971-12-27 | 1974-03-12 | Ricoh Kk | Electrophotographic light-sensitive material |
-
1972
- 1972-01-24 JP JP47009293A patent/JPS4949506B2/ja not_active Expired
-
1973
- 1973-01-15 GB GB200773A patent/GB1416232A/en not_active Expired
- 1973-01-19 DE DE2302625A patent/DE2302625C3/en not_active Expired
- 1973-01-24 FR FR7302510A patent/FR2169211B1/fr not_active Expired
- 1973-01-24 US US326563A patent/US3867140A/en not_active Expired - Lifetime
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
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US2980535A (en) * | 1954-01-05 | 1961-04-18 | Feldmuhle Papier Und Zellstoff | Light sensitive layers of synthetic materials |
US3252794A (en) * | 1956-11-14 | 1966-05-24 | Agfa Ag | Photoconductive layers and process for electrophotography |
US3244516A (en) * | 1959-04-09 | 1966-04-05 | Azoplate Corp | Electrophotographic mateiral and process |
US3307940A (en) * | 1959-05-30 | 1967-03-07 | Azoplate Corp | Electrophotographic process employing photoconductive polymers |
US3301676A (en) * | 1963-10-12 | 1967-01-31 | Azoplate Corp | Process and material for the production of electrophotographic images |
US3485625A (en) * | 1966-06-09 | 1969-12-23 | Eastman Kodak Co | Photoconductive elements containing 2,3,4,5-tetraaryl pyrrole |
US3484237A (en) * | 1966-06-13 | 1969-12-16 | Ibm | Organic photoconductive compositions and their use in electrophotographic processes |
US3595648A (en) * | 1967-03-23 | 1971-07-27 | Ricoh Kk | Poly-n-vinyl-3-nitro carbazole photoconductive material |
US3583869A (en) * | 1967-03-24 | 1971-06-08 | Ricoh Kk | Electrophotographic copying paper containing poly-n-vinyl-3-azo carbazole |
US3752668A (en) * | 1967-10-30 | 1973-08-14 | Addressograph Multigraph | Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers |
US3556785A (en) * | 1968-02-23 | 1971-01-19 | Addressograph Multigraph | Sensitizers for organic photoconductor comprising orazolone and butenolide derivatives of of fluorenone |
US3677752A (en) * | 1969-09-02 | 1972-07-18 | Eastman Kodak Co | Bis(dialkylaminoaryl)ethylene photoconductors |
US3674473A (en) * | 1970-10-06 | 1972-07-04 | Addressograph Multigraph | Cumulene containing photoconductive binder elements for use in electrophotography |
US3796572A (en) * | 1971-12-27 | 1974-03-12 | Ricoh Kk | Electrophotographic light-sensitive material |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3974167A (en) * | 1972-01-24 | 1976-08-10 | Ricoh Co., Ltd. | (7-Nitro-2-aza-9-fluorenylidene) malononitrile |
US4056391A (en) * | 1975-09-22 | 1977-11-01 | Xerox Corporation | Method for enhancing solid solution stability of electron acceptor molecules and electrophotographic compositions |
US4063947A (en) * | 1975-10-29 | 1977-12-20 | Xerox Corporation | Photoconductive insulating films comprising fluorenone-substituted oligomers |
US4474865A (en) * | 1983-08-08 | 1984-10-02 | Xerox Corporation | Layered photoresponsive devices |
KR100457523B1 (en) * | 2002-06-07 | 2004-11-17 | 삼성전자주식회사 | Single layered electrophotographic photoreceptor |
CN104035294A (en) * | 2013-03-07 | 2014-09-10 | 佳能株式会社 | Electrophotographic photoreceptor, electrophotographic devoce, PROCESS CARTRIDGE, and fused polycyclic aromatic compounds |
US20140255836A1 (en) * | 2013-03-07 | 2014-09-11 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, and electrophotographic apparatus and process cartridge each including the electrophotographic photosensitive member |
US9316931B2 (en) * | 2013-03-07 | 2016-04-19 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, electrophotographic apparatus, process cartridge, and condensed polycyclic aromatic compound |
CN104035294B (en) * | 2013-03-07 | 2017-09-22 | 佳能株式会社 | Electrophotographic photosensitive element, electronic photographing device, handle box and condensed polycyclc aromatic compound |
Also Published As
Publication number | Publication date |
---|---|
JPS4878935A (en) | 1973-10-23 |
FR2169211B1 (en) | 1979-01-12 |
GB1416232A (en) | 1975-12-03 |
FR2169211A1 (en) | 1973-09-07 |
DE2302625A1 (en) | 1973-07-26 |
DE2302625B2 (en) | 1975-04-17 |
JPS4949506B2 (en) | 1974-12-27 |
DE2302625C3 (en) | 1975-11-27 |
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