JPS5833548B2 - 光導電性組成物及び電子写真複写エレメント - Google Patents
光導電性組成物及び電子写真複写エレメントInfo
- Publication number
- JPS5833548B2 JPS5833548B2 JP48104489A JP10448973A JPS5833548B2 JP S5833548 B2 JPS5833548 B2 JP S5833548B2 JP 48104489 A JP48104489 A JP 48104489A JP 10448973 A JP10448973 A JP 10448973A JP S5833548 B2 JPS5833548 B2 JP S5833548B2
- Authority
- JP
- Japan
- Prior art keywords
- electron
- acceptor
- photoconductive
- donor
- compound
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 239000011247 coating layer Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 239000000370 acceptor Substances 0.000 description 34
- 239000010410 layer Substances 0.000 description 25
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 14
- 206010034972 Photosensitivity reaction Diseases 0.000 description 9
- 230000036211 photosensitivity Effects 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 7
- 230000001235 sensitizing effect Effects 0.000 description 7
- -1 9-dicyanomethylene fluorene compound Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 230000009918 complex formation Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000011888 foil Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- PMBBBTMBKMPOQF-UHFFFAOYSA-N 1,3,7-trinitrodibenzothiophene 5,5-dioxide Chemical compound O=S1(=O)C2=CC([N+](=O)[O-])=CC=C2C2=C1C=C([N+]([O-])=O)C=C2[N+]([O-])=O PMBBBTMBKMPOQF-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NGDPCAMPVQYGCW-UHFFFAOYSA-N dibenzothiophene 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3C2=C1 NGDPCAMPVQYGCW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VDFKURANQKCOAI-UHFFFAOYSA-N 1-nitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VDFKURANQKCOAI-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- ORMIJZCMQBMNFA-UHFFFAOYSA-N 3,6-dibromo-9-ethenylcarbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3N(C=C)C2=C1 ORMIJZCMQBMNFA-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- YPRJLDUOGDQQAK-UHFFFAOYSA-N 3-nitrodibenzothiophene 5,5-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 YPRJLDUOGDQQAK-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- FNALUOMDZYDJLK-UHFFFAOYSA-N 9-ethenyl-3-nitrocarbazole Chemical compound C1=CC=C2C3=CC([N+](=O)[O-])=CC=C3N(C=C)C2=C1 FNALUOMDZYDJLK-UHFFFAOYSA-N 0.000 description 1
- OGOYZCQQQFAGRI-UHFFFAOYSA-N 9-ethenylanthracene Chemical compound C1=CC=C2C(C=C)=C(C=CC=C3)C3=CC2=C1 OGOYZCQQQFAGRI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
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, 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
- Y10S430/10—Donor-acceptor complex photoconductor
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7212511A NL168059C (nl) | 1972-09-15 | 1972-09-15 | Elektrofotografisch donor-acceptor complex bevattend reproduktie-element, en werkwijze ter bereiding van een fotogeleidend preparaat. |
| NL7212511 | 1972-09-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4994337A JPS4994337A (enrdf_load_stackoverflow) | 1974-09-07 |
| JPS5833548B2 true JPS5833548B2 (ja) | 1983-07-20 |
Family
ID=19816942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48104489A Expired JPS5833548B2 (ja) | 1972-09-15 | 1973-09-14 | 光導電性組成物及び電子写真複写エレメント |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3905814A (enrdf_load_stackoverflow) |
| JP (1) | JPS5833548B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2346536A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2200553B1 (enrdf_load_stackoverflow) |
| GB (2) | GB1443450A (enrdf_load_stackoverflow) |
| NL (1) | NL168059C (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4066454A (en) * | 1973-11-19 | 1978-01-03 | Kabushiki Kaisha Ricoh | Electrophotographic light-sensitive material containing indenothiophenone or its derivative and process of preparing indenothiophenone and its derivative |
| JPS5184257A (ja) * | 1975-01-21 | 1976-07-23 | Fuji Xerox Co Ltd | Denshishashinyokododenzairyo |
| JPS5184256A (ja) * | 1975-01-21 | 1976-07-23 | Fuji Xerox Co Ltd | Denshishashinyokododenzairyo |
| US4514481A (en) * | 1984-03-09 | 1985-04-30 | Eastman Kodak Company | 4H-Thiopyran-1,1-dioxide and electrophotographic layers and elements comprising same |
| US4546059A (en) * | 1984-11-08 | 1985-10-08 | Xerox Corporation | Layered photoresponsive imaging members with sulfur incorporated dicyanomethylenefluorene carboxylate compositions |
| CN102807554B (zh) * | 2011-05-31 | 2014-07-09 | 海洋王照明科技股份有限公司 | 含萘、蒽、二苯并噻吩砜单元的有机半导体材料及其制备方法和应用 |
| CN102807556B (zh) * | 2011-05-31 | 2014-05-07 | 海洋王照明科技股份有限公司 | 含萘、蒽、二苯并噻吩砜单元的有机半导体材料及其制备方法和应用 |
| CN102807555B (zh) * | 2011-05-31 | 2014-05-28 | 海洋王照明科技股份有限公司 | 萘基蒽取代的二苯并噻吩砜有机半导体材料及其制备方法和应用 |
| CN102838585B (zh) * | 2011-06-22 | 2014-11-26 | 海洋王照明科技股份有限公司 | 含二苯并噻吩砜有机半导体材料的制备方法 |
| CN102850320B (zh) * | 2011-06-28 | 2015-01-21 | 海洋王照明科技股份有限公司 | 含二苯并噻吩砜化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU38469A1 (enrdf_load_stackoverflow) * | 1959-04-08 | |||
| US3287114A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| US3421891A (en) * | 1964-06-18 | 1969-01-14 | Matsushita Electric Industrial Co Ltd | Electrophotographic materials comprising brominated poly-n-vinyl carbazoles |
| US3545969A (en) * | 1965-07-26 | 1970-12-08 | Ibm | Method of inducing an electrostatic charge pattern on an insulating surface |
| US3547627A (en) * | 1966-05-02 | 1970-12-15 | Xerox Corp | Lithographic printing master and method employing a crystalline photoconductive imaging layer |
| GB1258244A (enrdf_load_stackoverflow) * | 1968-06-10 | 1971-12-22 | ||
| US3615384A (en) * | 1970-06-29 | 1971-10-26 | Ibm | Electrophotographic process employing vinyl bithiophene polymeric photoconductors |
| US3655378A (en) * | 1971-03-01 | 1972-04-11 | Eastman Kodak Co | Charge-transfer complexes of dibenzofuran-formaldehyde or dibenzothiophene-formaldehyde resins as photoconductive materials |
-
1972
- 1972-09-15 NL NL7212511A patent/NL168059C/xx not_active IP Right Cessation
-
1973
- 1973-09-05 US US394458A patent/US3905814A/en not_active Expired - Lifetime
- 1973-09-14 GB GB2891874A patent/GB1443450A/en not_active Expired
- 1973-09-14 JP JP48104489A patent/JPS5833548B2/ja not_active Expired
- 1973-09-14 GB GB4335373A patent/GB1443449A/en not_active Expired
- 1973-09-14 FR FR7333068A patent/FR2200553B1/fr not_active Expired
- 1973-09-15 DE DE19732346536 patent/DE2346536A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE2346536A1 (de) | 1974-03-28 |
| JPS4994337A (enrdf_load_stackoverflow) | 1974-09-07 |
| NL7212511A (enrdf_load_stackoverflow) | 1974-03-19 |
| NL168059B (nl) | 1981-09-16 |
| US3905814A (en) | 1975-09-16 |
| GB1443450A (en) | 1976-07-21 |
| NL168059C (nl) | 1982-02-16 |
| FR2200553B1 (enrdf_load_stackoverflow) | 1978-11-10 |
| GB1443449A (en) | 1976-07-21 |
| FR2200553A1 (enrdf_load_stackoverflow) | 1974-04-19 |
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