JPH0411586B2 - - Google Patents
Info
- Publication number
- JPH0411586B2 JPH0411586B2 JP62024933A JP2493387A JPH0411586B2 JP H0411586 B2 JPH0411586 B2 JP H0411586B2 JP 62024933 A JP62024933 A JP 62024933A JP 2493387 A JP2493387 A JP 2493387A JP H0411586 B2 JPH0411586 B2 JP H0411586B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- atom
- perylene
- linear
- 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 - Lifetime
Links
- -1 perylene compound Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 description 10
- 239000000057 synthetic resin Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- MMEBGSBVCUXECA-UHFFFAOYSA-N 4,10-dibromo-9-(2-methylpropoxycarbonyl)perylene-3-carboxylic acid Chemical compound C=12C3=CC=C(Br)C2=C(C(O)=O)C=CC=1C1=CC=C(Br)C2=C1C3=CC=C2C(=O)OCC(C)C MMEBGSBVCUXECA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- GSQMKXFQZMJUSR-UHFFFAOYSA-N 4,10-dicyano-9-(2-methylpropoxycarbonyl)perylene-3-carboxylic acid Chemical compound C=12C3=CC=C(C#N)C2=C(C(O)=O)C=CC=1C1=CC=C(C#N)C2=C1C3=CC=C2C(=O)OCC(C)C GSQMKXFQZMJUSR-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SDPOODQJUWAHOW-UHFFFAOYSA-N perylene-3,9-dicarboxylic acid Chemical class C=12C3=CC=CC2=C(C(O)=O)C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)O SDPOODQJUWAHOW-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/14—Perylene derivatives
- C09B3/18—Preparation from starting materials already containing the perylene nucleus
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- H10F77/00—Constructional details of devices covered by this subclass
- H10F77/40—Optical elements or arrangements
- H10F77/42—Optical elements or arrangements directly associated or integrated with photovoltaic cells, e.g. light-reflecting means or light-concentrating means
- H10F77/45—Wavelength conversion means, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/52—PV systems with concentrators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843400991 DE3400991A1 (de) | 1984-01-13 | 1984-01-13 | Verfahren zum flaechenmaessigen konzentrieren von licht und neue farbstoffe |
| DE3400991.4 | 1984-01-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62201966A JPS62201966A (ja) | 1987-09-05 |
| JPH0411586B2 true JPH0411586B2 (https=) | 1992-02-28 |
Family
ID=6224882
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60003436A Granted JPS60203650A (ja) | 1984-01-13 | 1985-01-14 | 平面への集光方法 |
| JP62024933A Granted JPS62201966A (ja) | 1984-01-13 | 1987-02-06 | 平面集光用の新規色素 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60003436A Granted JPS60203650A (ja) | 1984-01-13 | 1985-01-14 | 平面への集光方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4618694A (https=) |
| EP (2) | EP0264543B1 (https=) |
| JP (2) | JPS60203650A (https=) |
| DE (3) | DE3400991A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774025A (en) * | 1985-06-25 | 1988-09-27 | Hoechst Celanese Corporation | Nonlinear optical medium of a naphthoquinodimethane compound |
| US4773743A (en) * | 1985-06-25 | 1988-09-27 | Hoechst Celanese Corporation | Electrooptic light modulator device |
| JPH0772368B2 (ja) * | 1986-12-26 | 1995-08-02 | 日本エステル株式会社 | 螢光性ポリエステル繊維 |
| JPH02167723A (ja) * | 1988-12-22 | 1990-06-28 | Chisso Corp | 平面集光着色圧延シート又はフィルム及びその製造方法 |
| DE3933903A1 (de) * | 1989-10-11 | 1991-04-18 | Basf Ag | Fluoreszenzpigmente |
| US5359887A (en) * | 1992-08-03 | 1994-11-01 | Mc Donnell Douglas Corp | Pressure sensitive paint formulations and methods |
| DE4424817A1 (de) * | 1994-07-14 | 1996-01-18 | Basf Ag | Vernetzte Polymerteilchen mit Fluoreszenzfarbstoff |
| DE69904879T2 (de) * | 1998-06-15 | 2003-08-07 | Toyo Ink Mfg Co | Verbindung für organische Elektrolumineszensvorrichtung und organische Elektrolumineszensvorrichtung |
| DE19949382A1 (de) | 1999-10-13 | 2001-04-19 | Basf Ag | Verwendung feinteiliger, farbstoffhaltiger Polymerisate PF als farbgebenden Bestandteil in kosmetischen Mitteln |
| US6903505B2 (en) | 2001-12-17 | 2005-06-07 | General Electric Company | Light-emitting device with organic electroluminescent material and photoluminescent materials |
| US6893147B2 (en) | 2002-04-05 | 2005-05-17 | General Electric Company | Lamp lens or bezel with visual effect |
| US7718238B2 (en) | 2002-05-13 | 2010-05-18 | Sabic Innovative Plastics Ip B.V. | Plastics articles such as bottles with visual effect |
| US20060107993A1 (en) * | 2004-11-19 | 2006-05-25 | General Electric Company | Building element including solar energy converter |
| US20090032083A1 (en) * | 2005-09-15 | 2009-02-05 | Torrance Jerry B | Solar Collection Device |
| US20070137696A1 (en) * | 2005-12-21 | 2007-06-21 | Hans-Joachim Krokoszinski | Solar panels, methods of manufacture thereof and articles comprising the same |
| EP2262863B1 (de) | 2008-03-03 | 2013-09-04 | Basf Se | Mikrokapseln, ihre herstellung und verwendung |
| US8304647B2 (en) * | 2008-08-19 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8299354B2 (en) * | 2008-08-19 | 2012-10-30 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8314325B2 (en) * | 2008-08-19 | 2012-11-20 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8304645B2 (en) * | 2008-08-19 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| WO2012094409A2 (en) | 2011-01-05 | 2012-07-12 | Nitto Denko Corporation | Wavelength conversion perylene diester chromophores and luminescent films |
| JP5468119B2 (ja) | 2011-09-26 | 2014-04-09 | 日東電工株式会社 | 増強された太陽光集光効率のための高蛍光性かつ光安定性の発色団 |
| TW201317327A (zh) | 2011-10-05 | 2013-05-01 | Nitto Denko Corp | 波長轉換膜、其形成方法以及其使用方法 |
| WO2013067288A1 (en) * | 2011-11-04 | 2013-05-10 | Nitto Denko Corporation | Microstructured wavelength conversion films for enhanced solar harvesting efficiency |
| US9399730B2 (en) | 2011-12-06 | 2016-07-26 | Nitto Denko Corporation | Wavelength conversion material as encapsulate for solar module systems to enhance solar harvesting efficiency |
| CN104428390A (zh) * | 2012-02-01 | 2015-03-18 | 日东电工株式会社 | 用于增强太阳能收集效率的压敏粘合剂型波长转换带 |
| US20150041052A1 (en) * | 2012-02-01 | 2015-02-12 | Nitto Denko Corporation | Wavelength conversion layer on a glass plate to enhance solar harvesting efficiency |
| CN104583161B (zh) * | 2012-08-30 | 2016-12-14 | 巴斯夫欧洲公司 | 作为有机电子材料和染料的结构单元的方便制备的萘和苝衍生物 |
| KR20150135346A (ko) * | 2013-03-26 | 2015-12-02 | 닛토덴코 가부시키가이샤 | 다중 광안정성 유기 발색단을 갖는 파장 변환 필름 |
| CN103626678B (zh) * | 2013-12-09 | 2015-04-15 | 南京信息工程大学 | 3,4,9,10-四氰基苝的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB254310A (https=) * | 1900-01-01 | |||
| US3557218A (en) * | 1965-10-20 | 1971-01-19 | Geigy Chem Corp | Polysubstituted dihydropyrenes |
| DE2512516C2 (de) * | 1975-03-21 | 1985-01-03 | Basf Ag, 6700 Ludwigshafen | Perylen-3,4,9,10-tetracarbonsäureester |
| AT351615B (de) * | 1975-12-03 | 1979-08-10 | Siemens Ag | Anordnung zur passiven helligkeitsverstaerkung von ein- oder mehrfarbigen anzeigevor- richtungen |
| CH612541A5 (https=) * | 1976-05-06 | 1979-07-31 | Fraunhofer Ges Forschung | |
| DE2620115C2 (de) * | 1976-05-06 | 1983-08-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 8000 München | Vorrichtung zur Umwandlung von Lichtenergie in elektrische Energie |
| DE2851513C3 (de) * | 1978-11-29 | 1993-11-18 | Bayer Ag | Lichtsammelsystem |
| US4379934A (en) * | 1980-01-19 | 1983-04-12 | Basf Aktiengesellschaft | Process for two-dimensionally concentrating light, and novel perylene-3,4,9,10-tetracarboxylic acid diimides |
| DE3149620A1 (de) * | 1981-12-15 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Lichtsammelsysteme unter verwendung von halogenierten perylenderivaten als lichtwandler |
-
1984
- 1984-01-13 DE DE19843400991 patent/DE3400991A1/de not_active Withdrawn
- 1984-12-20 DE DE8787108848T patent/DE3484397D1/de not_active Expired - Lifetime
- 1984-12-20 DE DE8484115970T patent/DE3472864D1/de not_active Expired
- 1984-12-20 EP EP87108848A patent/EP0264543B1/de not_active Expired - Lifetime
- 1984-12-20 EP EP84115970A patent/EP0156997B1/de not_active Expired
-
1985
- 1985-01-11 US US06/690,524 patent/US4618694A/en not_active Expired - Lifetime
- 1985-01-14 JP JP60003436A patent/JPS60203650A/ja active Granted
-
1987
- 1987-02-06 JP JP62024933A patent/JPS62201966A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0156997A1 (de) | 1985-10-09 |
| JPS62201966A (ja) | 1987-09-05 |
| EP0156997B1 (de) | 1988-07-20 |
| DE3400991A1 (de) | 1985-07-18 |
| US4618694A (en) | 1986-10-21 |
| DE3472864D1 (en) | 1988-08-25 |
| EP0264543A3 (en) | 1988-08-24 |
| EP0264543A2 (de) | 1988-04-27 |
| JPS60203650A (ja) | 1985-10-15 |
| EP0264543B1 (de) | 1991-04-03 |
| DE3484397D1 (de) | 1991-05-08 |
| JPH0238135B2 (https=) | 1990-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0411586B2 (https=) | ||
| JP6871898B2 (ja) | 波長変換のための高蛍光性光安定性発色団 | |
| JP5976675B2 (ja) | 波長変換ペリレンジエステル発色団および発光膜 | |
| KR20150135346A (ko) | 다중 광안정성 유기 발색단을 갖는 파장 변환 필름 | |
| US6300502B1 (en) | Multi-armed chromophores with very large two-photon absorption cross-sections | |
| EP3197890B1 (en) | Disubstituted diaryloxybenzoheterodiazole compounds | |
| JPS5989302A (ja) | 集光体の製造法 | |
| EP0426717A1 (de) | Optische datenspeicher. | |
| WO2015023574A1 (en) | Luminescent solar concentrator utilizing organic photostable chromophore compounds | |
| JP2014185286A (ja) | ベンゾトリアゾール構造を有する発色団およびそれを用いた波長変換発光媒体 | |
| CN109762000B (zh) | 基于1,8-萘酰亚胺单元的螺噁嗪类氢离子荧光探针化合物及其合成方法和应用 | |
| CA2119840A1 (en) | Optical sensor for the determination of cations | |
| WO2014010305A1 (ja) | 化合物、太陽電池モジュール及び太陽光発電装置 | |
| JPH0424397B2 (https=) | ||
| JP2013103911A (ja) | 赤外吸収フタロシアニン | |
| JPS62148571A (ja) | 蛍光性のアリ−ルオキシ置換ペリレン−３，４，９，１０−テトラカルボン酸ジイミド | |
| US9403825B2 (en) | Compound, solar cell module, and photovoltaic power generation device | |
| US4492648A (en) | Light-collecting systems using halogenated perylene derivatives as light converters | |
| ITUB20155558A1 (it) | Composti diarilossibenzoeterodiazolici disostituiti | |
| JP2014240371A (ja) | 化合物、太陽電池モジュール及び太陽光発電装置 | |
| KR20050103943A (ko) | 수용성 형광 페릴렌테트라카르복스디이미드 | |
| EP0046164A2 (de) | Verwendung von Perylenderivaten für Fluoreszenzzwecke und neue Perylenderivate | |
| JPS6342943B2 (https=) | ||
| JPS6354753B2 (https=) | ||
| AU717688B2 (en) | Donor-substituted oxindigo derivatives and their use as colourants |