DE3854534T2 - Elektrophotographische Platten, die ein metallisiertes Derivat des Naphthalocyanins enthalten. - Google Patents
Elektrophotographische Platten, die ein metallisiertes Derivat des Naphthalocyanins enthalten.Info
- Publication number
- DE3854534T2 DE3854534T2 DE3854534T DE3854534T DE3854534T2 DE 3854534 T2 DE3854534 T2 DE 3854534T2 DE 3854534 T DE3854534 T DE 3854534T DE 3854534 T DE3854534 T DE 3854534T DE 3854534 T2 DE3854534 T2 DE 3854534T2
- Authority
- DE
- Germany
- Prior art keywords
- naphthalocyanine
- electrophotographic plate
- plate according
- layer
- group
- 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 - Fee Related
Links
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 title claims description 69
- 229910052751 metal Inorganic materials 0.000 claims description 56
- 239000002184 metal Substances 0.000 claims description 56
- -1 bis(tripropylsiloxy)germanium Chemical compound 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 31
- 229910052732 germanium Inorganic materials 0.000 claims description 23
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000012860 organic pigment Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052718 tin Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- CXUCBMXRZGCJIZ-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-2-[4-(dipropylamino)phenyl]-1,3-oxazol-4-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(CCC)CCC)=CC=C1C1=NC(C=2C=CC(=CC=2)N(C)C)=C(C=2C(=CC=CC=2)Cl)O1 CXUCBMXRZGCJIZ-UHFFFAOYSA-N 0.000 claims description 2
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- 238000010438 heat treatment Methods 0.000 description 3
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- 150000003384 small molecules Chemical class 0.000 description 3
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- 239000010409 thin film Substances 0.000 description 3
- FBGKGORFGWHADY-UHFFFAOYSA-L tin(2+);dihydroxide Chemical compound O[Sn]O FBGKGORFGWHADY-UHFFFAOYSA-L 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GSKKDUBVUYUVPN-UHFFFAOYSA-N n,n-diethyl-4-(2-phenyl-1,3-dihydropyrazol-5-yl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=CCN(C=2C=CC=CC=2)N1 GSKKDUBVUYUVPN-UHFFFAOYSA-N 0.000 description 1
- ZNPWYAMBOPRTHW-UHFFFAOYSA-N naphthalene-1,2-dicarbonitrile Chemical compound C1=CC=CC2=C(C#N)C(C#N)=CC=C21 ZNPWYAMBOPRTHW-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 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
- 230000001699 photocatalysis Effects 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000008096 xylene Substances 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
- G03G5/0664—Dyes
- G03G5/0696—Phthalocyanines
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62019155A JPS63186251A (ja) | 1987-01-29 | 1987-01-29 | 金属ナフタロシアニン誘導体膜及び電子写真感光体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3854534D1 DE3854534D1 (de) | 1995-11-09 |
| DE3854534T2 true DE3854534T2 (de) | 1996-04-18 |
Family
ID=11991525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3854534T Expired - Fee Related DE3854534T2 (de) | 1987-01-29 | 1988-01-29 | Elektrophotographische Platten, die ein metallisiertes Derivat des Naphthalocyanins enthalten. |
Country Status (4)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0752300B2 (ja) * | 1987-03-19 | 1995-06-05 | 三菱油化株式会社 | 電子写真感光体 |
| DE69028681T2 (de) * | 1989-11-13 | 1997-02-20 | Canon Kk | Lichtempfindliches Element, elektrophotographischer Apparat und ihn benutzendes Bildherstellungsverfahren |
| DE69116933T2 (de) * | 1990-06-04 | 1996-07-11 | Canon Kk | Lichtempfindliches Element zur Elektrophotographie |
| US5260435A (en) * | 1990-07-23 | 1993-11-09 | Nippon Oil And Fats Co., Ltd. | Derivative of naphthalocyanine containing perfluoroalkyl group, process for preparing the same and optical recording medium |
| JP3072689B2 (ja) * | 1993-04-02 | 2000-07-31 | 富士ゼロックス株式会社 | メトキシガリウムフタロシアニン化合物およびそれを用いた電子写真感光体 |
| DE69524044T2 (de) * | 1994-12-22 | 2002-07-04 | Ciba Speciality Chemicals Holding Inc., Basel | Elektrophotographischer Photorezeptor |
| US7245851B2 (en) * | 2003-11-26 | 2007-07-17 | Canon Kabushiki Kaisha | Electrophotographic apparatus |
| JP4333510B2 (ja) * | 2004-07-22 | 2009-09-16 | 富士ゼロックス株式会社 | 赤外線吸収剤、電子写真用トナーとそれを用いた画像形成装置 |
| US8848047B2 (en) | 2006-09-28 | 2014-09-30 | Fujifilm Corporation | Imaging device and endoscopic apparatus |
| JP4951303B2 (ja) * | 2006-09-28 | 2012-06-13 | 富士フイルム株式会社 | 内視鏡用撮像素子 |
| EP2750191A1 (en) | 2007-03-12 | 2014-07-02 | Fujifilm Corporation | Photoelectric conversion element and solid-state imaging device |
| JP5270114B2 (ja) | 2007-06-15 | 2013-08-21 | 富士フイルム株式会社 | 固体撮像素子 |
| JP5216279B2 (ja) * | 2007-08-23 | 2013-06-19 | 富士フイルム株式会社 | 有機半導体材料、該材料を含む膜、有機電子デバイス及び赤外色素組成物 |
| JP5499990B2 (ja) | 2010-08-19 | 2014-05-21 | コニカミノルタ株式会社 | 静電荷像現像用シアントナー |
| WO2022064984A1 (ja) | 2020-09-25 | 2022-03-31 | 三菱瓦斯化学株式会社 | シアニン化合物及び光電変換素子 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094535A (en) * | 1961-01-03 | 1963-06-18 | Malcolm E Kenney | Germanium phthalocyanines |
| US4131609A (en) * | 1978-02-23 | 1978-12-26 | The United States Of America As Represented By The Secretary Of The Navy | Silicon-phthalocyanine-siloxy monomers |
| US4132842A (en) * | 1978-02-23 | 1979-01-02 | The United States Of America As Represented By The Secretary Of The Navy | Silicon-phthalocyanine-siloxane polymers |
| JPS58158649A (ja) * | 1982-03-15 | 1983-09-20 | Nippon Telegr & Teleph Corp <Ntt> | 積層型電子写真感光体 |
| US4492750A (en) * | 1983-10-13 | 1985-01-08 | Xerox Corporation | Ablative infrared sensitive devices containing soluble naphthalocyanine dyes |
| US4557989A (en) * | 1984-09-13 | 1985-12-10 | Xerox Corporation | Photoresponsive imaging members with dihydroxy metal phthalocyanine compositions |
| JPS61177287A (ja) * | 1985-02-04 | 1986-08-08 | ヘキスト・セラニーズ・コーポレーション | 発色団を含有する情報記録媒体 |
| JPH0717092B2 (ja) * | 1985-02-04 | 1995-03-01 | ヘキスト・セラニ−ズ・コ−ポレ−ション | 有機大環状発色団を含有する光情報記憶媒体 |
| US4725525A (en) * | 1985-02-04 | 1988-02-16 | Hoebbst Celanese Corporation | Recording information media comprising chromophores |
| JPS6290291A (ja) * | 1985-05-31 | 1987-04-24 | Mitsui Toatsu Chem Inc | 光記録媒体 |
| JPS6253809A (ja) * | 1985-09-02 | 1987-03-09 | Matsushita Electric Ind Co Ltd | 反応性液状樹脂成形用のゴム型の製造方法 |
| US4749637A (en) * | 1986-04-24 | 1988-06-07 | Hitachi Chemical Co., Ltd. | Electrophotographic plate with silicon naphthalocyanine |
| US4927735A (en) * | 1987-01-07 | 1990-05-22 | Hitachi Chemical Company, Ltd. | Novel naphthalocyanine dye, method for preparing the same, and optical information recording medium employing the same |
| JPH0749411B2 (ja) * | 1987-03-23 | 1995-05-31 | 日立化成工業株式会社 | ５−又は６−アルコキシカルボニル−２，３−ジシアノナフタレンおよびその製造法 |
-
1987
- 1987-01-29 JP JP62019155A patent/JPS63186251A/ja active Granted
-
1988
- 1988-01-25 US US07/147,694 patent/US4886721A/en not_active Expired - Fee Related
- 1988-01-29 DE DE3854534T patent/DE3854534T2/de not_active Expired - Fee Related
- 1988-01-29 EP EP88300797A patent/EP0277039B1/en not_active Expired - Lifetime
-
1989
- 1989-10-06 US US07/418,087 patent/US5021563A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0277039B1 (en) | 1995-10-04 |
| EP0277039A3 (en) | 1989-11-23 |
| JPS63186251A (ja) | 1988-08-01 |
| EP0277039A2 (en) | 1988-08-03 |
| JPH0435754B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-06-12 |
| US5021563A (en) | 1991-06-04 |
| US4886721A (en) | 1989-12-12 |
| DE3854534D1 (de) | 1995-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |