DE2851513C3 - Light collection system - Google Patents
Light collection systemInfo
- Publication number
- DE2851513C3 DE2851513C3 DE2851513A DE2851513A DE2851513C3 DE 2851513 C3 DE2851513 C3 DE 2851513C3 DE 2851513 A DE2851513 A DE 2851513A DE 2851513 A DE2851513 A DE 2851513A DE 2851513 C3 DE2851513 C3 DE 2851513C3
- Authority
- DE
- Germany
- Prior art keywords
- light collection
- collection system
- dye
- formula
- denotes
- 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
- 239000000975 dye Substances 0.000 claims description 22
- 239000004033 plastic Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 230000005540 biological transmission Effects 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000007850 fluorescent dye Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- CBKYRRMIYDLSFF-UHFFFAOYSA-N C=12C3=CC=CC2=C(C(=O)OCCCC)C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)OCCCC Chemical compound C=12C3=CC=CC2=C(C(=O)OCCCC)C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)OCCCC CBKYRRMIYDLSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- STWCWAOCWOCVDY-UHFFFAOYSA-N CCOC(=O)C1=CC=C2C3=C4C(=CC=C3)C(=CC=C4C5=C2C1=CC=C5)C(=O)OCC Chemical class CCOC(=O)C1=CC=C2C3=C4C(=CC=C3)C(=CC=C4C5=C2C1=CC=C5)C(=O)OCC STWCWAOCWOCVDY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- JSQFXMIMWAKJQJ-UHFFFAOYSA-N [9-(2-carboxyphenyl)-6-(ethylamino)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(NCC)=CC=C2C=1C1=CC=CC=C1C(O)=O JSQFXMIMWAKJQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000006383 alkylpyridyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/054—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means
- H01L31/055—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means where light is absorbed and re-emitted at a different wavelength by the optical element directly associated or integrated with the PV cell, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
-
- 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
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Electromagnetism (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Lichtsammelsysteme (fluorescent collectors) können beispielsweise in Verbindung mit Solarzellen zur Umwandlung der Sonnenenergie in andere Energiearten dienen. Die ökonomische Verwendbarkeit eines Lichtsammelsystems wird in hohem Maße von der Brauchbarkeit des in ihm als Lichtwandler eingesetzten Farbstoffs bestimmt. An die optische Qualität dieses Farbstoffs werden extreme Anforderungen gestellt (Applied Physics 14, 123-139 [1977]). Lichtsammelsysteme sind aus den Literaturstellen J. Appl. Phys. 40, 3544-3547 (1969) und DE-OS 26 20 115 bekannt.Light collecting systems (fluorescent collectors) can be used, for example, in conjunction with solar cells for conversion serve solar energy in other types of energy. The economic usability of a light collection system is largely dependent on the usability of the dye used in it as a light converter certainly. Extreme demands are placed on the optical quality of this dye (Applied Physics 14, 123-139 [1977]). Light collection systems are from the literature J. Appl. Phys. 40, 3544-3547 (1969) and DE-OS 26 20 115 known.
Die vorliegende Erfindung betrifft neue Lichtsammelsysteme, bei denen das Verhältnis von Emissions- zu Absorptionsfläche 1 : 100 bis 1 : 1000 beträgt, und die einen fluoreszierenden Farbstoff in einem optisch verwendbaren Kunststoff enthalten, dadurch gekennzeichnet, daß es sich bei dem Farbstoff um einen Farbstoff der FormelThe present invention relates to new light collection systems in which the ratio of emission to Absorption area is 1: 100 to 1: 1000, and which is a fluorescent dye in an optically usable Contain plastic, characterized in that the dye is a dye of the formula
handelt, in der
R Wasserstoff oder einen gegebenenfalls substituieren Kohlenwasserstoff- oder heterocyclischen Rest,
Y Sauerstoff oder -NR, mit der vorstehend angegebenen Bedeutung von R und
R₁ Wasserstoff oder die Gruppeacts in the
R is hydrogen or an optionally substituted hydrocarbon or heterocyclic radical,
Y is oxygen or -NR, with the meaning of R and
R₁ is hydrogen or the group
in der Y und R die oben angegebene Bedeutung haben und n 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 oder 16 bezeichnen, wobei für den Fall, daß R₁in which Y and R have the meaning given above and n denotes 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16, in the event that R₁
bedeutet, die jeweils peri-ständigen Restemeans the respective peri-permanent residues
auch unter Ausbildung einer cyclischen Imidstruktur zusammentreten können, wobei weiterhin der Farbstoff der Formel (I) in einer 0,5-2 mM-Lösung bei einer Schichtdicke von 10 cm einen Anstieg der Transmission von 0 auf 100% aufweist, wenn die Wellenlänge um 25-200 nm verändert wird.can also come together to form a cyclic imide structure, wherein the dye of the formula (I) in a 0.5-2 mM solution with a layer thickness of 10 cm has an increase in transmission from 0 to 100% when the wavelength is around 25-200 nm is changed.
In den erfindungsgemäßen Lichtsammelsystemen sind Farbstoffe der FormelIn the light collection systems according to the invention, dyes are of the formula
in der R′ einen gegebenenfalls substituierten Kohlenwasserstoff oder heterocyclischen Rest bezeichnet, wobei die genannten Reste durch in der Farbstoffchemie übliche wasserlöslichmachende Gruppen oder Atome substituiert sein können, gut geeignet.in which R 'denotes an optionally substituted hydrocarbon or heterocyclic radical, where the residues mentioned by water-solubilizing groups or atoms customary in dye chemistry can be substituted, well suited.
R′ steht bevorzugt für C₁-C₅-Alkyl wie Methyl, n- und i-Propyl, t-Butyl; besonders bevorzugt steht R′ für Ethyl und i-Butyl.R 'is preferably C₁-C₅-alkyl such as methyl, n- and i-propyl, t-butyl; R 'particularly preferably stands for Ethyl and i-butyl.
Weiterhin sind für die erfindungsgemäßen Lichtsammelsysteme Farbstoffe der Formel Furthermore, dyes of the formula are for the light collection systems according to the invention
in der R und n die oben angegebene Bedeutung haben und das Farbstoffmolekül 0 bis 16 Chloratome aufweist, gut geeignet.in which R and n have the meaning given above and the dye molecule has 0 to 16 chlorine atoms, well suited.
In Formel III steht R bevorzugt für gegebenenfalls durch Halogen, Trifluormethyl, Alkyl, Halogenalkyl, Alkoxy substituiertes Phenyl, Alkylpyridyl, Alkyl, Alkoxyalkyl, Alkoxyamino, Arylamino, Aryloxy, wobei unter Alkyl insbesondere C₁-C₆-Alkyl, unter Halogen Chlor, Brom, Fluor, unter Alkoxy C₁-C₆-Alkoxy, unter Aryl Phenyl und Naphthyl zu verstehen sind.In formula III, R preferably represents optionally halogen, trifluoromethyl, alkyl, haloalkyl, Alkoxy substituted phenyl, alkyl pyridyl, alkyl, alkoxyalkyl, alkoxyamino, arylamino, aryloxy, where under alkyl in particular C₁-C₆-alkyl, under halogen chlorine, bromine, fluorine, under alkoxy C₁-C₆-alkoxy, under Aryl phenyl and naphthyl are to be understood.
Die in die neuen Lichtsammelsyseme einsetzbaren Verbindungen sind bekannt (s. z. B. Ullmann, 3. Aufl., 3. Band, S. 722 ff; DE-OS 24 51 781; DE-OS 24 51 782; DE-OS 21 39 688).The compounds that can be used in the new light collection systems are known (see, for example, Ullmann, 3rd ed., 3rd volume, p. 722 ff; DE-OS 24 51 781; DE-OS 24 51 782; DE-OS 21 39 688).
Die neuen Lichtsammelsysteme sind geeignet, einfallende diffuse elektromagnetische Strahlung zu absorbieren und in einem gegenüber der Umgebung optisch dichteren Medium nahezu verlustlos zu emittieren, wobei der Hauptteil des Emissionslichtes total reflektiert im Medium verbleibt.The new light collection systems are suitable for absorbing incident diffuse electromagnetic radiation and emit almost losslessly in a medium that is optically denser than the surroundings, the main part of the emission light remains totally reflected in the medium.
Nur der Anteil des emittierten Lichtes, dessen Emissionsbande weitgehend frei von Absorption ist, ist für den erfindungsgemäßen Zweck aufweist.Only the proportion of the emitted light whose emission band is largely free of absorption is for the has purpose according to the invention.
Deshalb ist es zweckmäßig, die Farbstoffe der Formel (I) vor Einsatz in die Lichtsammelsysteme besonders zu reinigen. Die Erfindung betrifft demnach bevorzugt Lichtsammelsysteme, die dadurch gekennzeichnet sind, daß sie einen Farbstoff der Formel I bzw. II oder III enthalten, der in einer Lösung die 0,5-2 mM der erfindungsgemäß einsetzbaren Farbstoffe im Liter enthält, bei einer Schichtdicke von 10 cm einen Anstieg der Transmission von 0 auf 100% aufweist, wenn die Wellenlänge um 25-200 nm, vorzugsweise 35-100 nm, verändert wird.It is therefore advisable to use the dyes of the formula (I) in particular before they are used in the light collection systems to clean. The invention accordingly preferably relates to light collection systems which are characterized in that are that they contain a dye of formula I or II or III, which in a solution the 0.5-2 mM contains dyes which can be used according to the invention in liters, with a layer thickness of 10 cm, an increase has the transmission from 0 to 100% if the wavelength is around 25-200 nm, preferably 35-100 nm, is changed.
Die Reinigung der Farbstoffe kann in günstigen Fällen durch mehrfache sorgfältige Kristallisation erfolgen. Zumeist ist eine säulenchromatographische Trennung an festen Trägern wie Al₂O₃ oder SiO₂ erforderlich. Besonders schonend erhält man hohe Reinheitsgrade verteilungschromatographisch, z. B. durch Steady-State- (O′Keefe)- oder Gegenstromverteilung nach Craig.In favorable cases, the dyes can be cleaned by repeated careful crystallization. Usually, column chromatography separation on solid supports such as Al₂O₃ or SiO₂ is required. Especially gently you get high purity distribution chromatography, z. B. by steady state (O′Keefe) - or countercurrent distribution according to Craig.
Die neuen Lichtsammelsysteme können z. B. in Verbindung mit Solarzellen zur Nutzbarmachung der Sonnenenergie und in Szintillatoren bekannter Art [s. z. B. J. B. Birks: The Theory and Practice of Scintillation Counting Pergamon Press, London 1964); J. Opt. Am. 39, 912 (1949); J. Appl. Phys. 40, 3544 (1969); Nuclear Instruments a. Methods 89, 111-123 (1970)] Verwendung finden. Darüber hinaus eignen sie sich in Verbindung mit elektronischen Steuerungen als Anzeigevorrichtungen mit sehr geringem Energieverbrauch. Darüber hinaus eignen sie sich ohne elektronische Bauteile für vielerlei Anzeige-, Hinweis- und Markierungszwecke, z. B. in passiven Anzeigeelementen, Hinweis- und Verkehrszeichen wie Ampeln.The new light collection systems can e.g. B. in connection with solar cells to harness the Solar energy and in scintillators of a known type [s. e.g. B. J. B. Birks: The Theory and Practice of Scintillation Counting Pergamon Press, London 1964); J. Opt. Am. 39, 912 (1949); J. Appl. Phys. 40: 3544 (1969); Nuclear Instruments a. Methods 89, 111-123 (1970)] find use. They are also suitable in combination with electronic controls as display devices with very low energy consumption. Furthermore They are suitable for electronic display, information and marking purposes, e.g. for electronic components. B. in passive display elements, signs and traffic signs such as traffic lights.
Geeignete Kunststoffe, wie sie z. B. zum Sammeln von Licht in Verbindung mit Solarzellen und in passiven Anzeigeelementen eingesetzt werden, sind z. B. Homo- und Copolymerisate der Acrylsäure(derivate) oder Polycarbonate.Suitable plastics, such as. B. for collecting light in connection with solar cells and in passive Display elements are used, for. B. homo- and copolymers of acrylic acid (derivatives) or Polycarbonates.
Die erfindungsgemäßen Lichtsammelsysteme sind im hohen Maße vorteilhaft, da sie neben einer guten Quantenausbeute und einem hohen Verstärkungsfaktor ausgezeichnete Lichtechtheit aufweisen und damit eine ökonomische Verwendbarkeit gewährleisten.The light collection systems according to the invention are highly advantageous because, in addition to a good one Quantum yield and a high gain factor have excellent light fastness and thus a Ensure economic usability.
Es muß als überraschend bezeichnet werden, daß die Farbstoffe der Formel (I) sich zur vorteilhaften Verwendung in Lichtsammelsysteme eignen, da zahlreiche hervorragende fluoreszierende Farbstoffe wie z. B. Rhodamin G nicht brauchbar sind. Ebenso sind die schon sehr weitgehenden Forderungen, die an die optische Qualität von Laserfarbstoffen gestellt werden, in vielen Fällen nicht ausreichend, um die Verwendung dieser Farbstoffe in Lichtsammelsystemen zu empfehlen.It must be described as surprising that the dyes of the formula (I) are for advantageous use in light collection systems because numerous excellent fluorescent dyes such. B. Rhodamine G cannot be used. Likewise, the already very extensive demands on the optical Quality of laser dyes are, in many cases, insufficient to use of these dyes in light collection systems.
Zur Reinigung werden 2 g 3,9-Perylendicarbonsäure-di-i-butylester coloristisch geeigneter Qualität in Chloroform gelöst. Diese Lösung wird auf eine Säule (8 cm ⌀) augebracht, die 1 kg Kieselgel (Herst. Merck) enthält. Man eluiert mit Chloroform : Methanol = 5 : 2. Die ersten schmutzig blauvioletten Farbstoffanteile werden verworfen. Die Hauptfraktion des Eluats wird eingedampft und aus Chloroform umkristallisiert. Man erhält leuchtend orangerote Kristalle vom Fp. 198°C.For cleaning, 2 g of 3,9-perylenedicarboxylic acid di-i-butyl ester of coloristically suitable quality in Chloroform dissolved. This solution is applied to a column (8 cm ⌀) containing 1 kg of silica gel (manufacturer Merck) contains. It is eluted with chloroform: methanol = 5: 2. The first dirty blue-violet dye components are discarded. The main fraction of the eluate is evaporated and recrystallized from chloroform. Man receives bright orange-red crystals of mp. 198 ° C.
Das so erhaltene Produkt wird zu 0,05% in handelsübliches Polymethacrylat eingearbeitet und das Gemisch zu Platten vergossen. Das System ergibt bei einer Anregungswellenlänge von 430 nm eine Quantenausbeute von 82%. Die Transmission beträgt 0% bei 525 nm und 100% bei 535 nm.0.05% of the product thus obtained is incorporated into commercially available polymethacrylate and the mixture cast into plates. The system produces a quantum yield at an excitation wavelength of 430 nm of 82%. The transmission is 0% at 525 nm and 100% at 535 nm.
Gute Lichtsammelsysteme erhält man auch, wenn nach obigen Angaben 3,9-Perylendicarbonsäure-diethyl- ester und -dinonylester an Stelle des Di-i-butylesters eingesetzt werden.Good light collection systems are also obtained if, according to the above information, 3,9-perylenedicarboxylic acid diethyl esters and dinonyl esters are used in place of the di-i-butyl ester.
Effektive Lichtsammelsysteme erhält man auch unter Verwendung der nachfolgend aufgeführten Farbstoffe anstelle von 3,9-Perylendicarbonsäure-di-i-butylester gemäß Beispiel 1. Effective light collection systems can also be obtained using the dyes listed below instead of 3,9-perylenedicarboxylic acid di-i-butyl ester according to Example 1.
Claims (9)
R Wasserstoff oder einen gegebenenfalls substituierten Kohlenwasserstoff- oder heterocylischen Rest,
Y Sauerstoff oder -NR, mit der vorstehend angegebenen Bedeutung von R und
R₁ Wasserstoff oder die Gruppe in der Y und R die oben angegebene Bedeutung haben und
n 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 oder 16 bezeichnen,
wobei für den Fall, daß R₁ bedeutet, die jeweils peri-ständigen Reste auch unter Ausbildung einer cyclischen Imidstruktur zusammentreten können, wobei weiterhin der Farbstoff der Formel (I) in einer 0,5- 2 mM-Lösung bei einer Schichtdicke von 10 cm einen Anstieg der Transmission von 0 auf 100% aufweist, wenn die Wellenlänge um 25-200 nm verändert wird. 1. Light collection system in which the ratio of emission to absorption area is 1: 100 to 1: 1000, and which contains a fluorescent dye in an optically usable plastic, characterized in that the dye is a dye of the formula acts in the
R is hydrogen or an optionally substituted hydrocarbon or heterocyclic radical,
Y is oxygen or -NR, with the meaning of R and
R₁ is hydrogen or the group in which Y and R have the meaning given above and
n denotes 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16,
in the event that R₁ means the respective peri-permanent residues can also come together to form a cyclic imide structure, the dye of the formula (I) furthermore having an increase in transmission from 0 to 100% in a 0.5-2 mM solution at a layer thickness of 10 cm when the wavelength is around 25 -200 nm is changed.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2851513A DE2851513C3 (en) | 1978-11-29 | 1978-11-29 | Light collection system |
JP15306879A JPS5575480A (en) | 1978-11-29 | 1979-11-28 | Fluorescent collector |
JP63206503A JPS6485282A (en) | 1978-11-29 | 1988-08-22 | Fluorescent collector |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2851513A DE2851513C3 (en) | 1978-11-29 | 1978-11-29 | Light collection system |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2851513A1 DE2851513A1 (en) | 1980-06-12 |
DE2851513C2 DE2851513C2 (en) | 1986-10-30 |
DE2851513C3 true DE2851513C3 (en) | 1993-11-18 |
Family
ID=6055762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2851513A Expired - Lifetime DE2851513C3 (en) | 1978-11-29 | 1978-11-29 | Light collection system |
Country Status (2)
Country | Link |
---|---|
JP (2) | JPS5575480A (en) |
DE (1) | DE2851513C3 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9382424B2 (en) | 2011-09-26 | 2016-07-05 | Nitto Denko Corporation | Highly-fluorescent and photo-stable chromophores for enhanced solar harvesting efficiency |
US9394479B2 (en) | 2011-10-05 | 2016-07-19 | Nitto Denko Corporation | Wavelength conversion film having pressure sensitive adhesive layer to enhance solar harvesting efficiency |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE3017185A1 (en) * | 1980-05-05 | 1981-11-19 | Hoechst Ag, 6000 Frankfurt | PERYLENE-3,4,9,10-TETRACARBONIC ACID MONOANHYDRIDE MONOIMIDES, METHOD FOR PRODUCING SUCH A COMPOUND AND THEIR USE |
DE3032546A1 (en) * | 1980-08-29 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | METHOD FOR CONCENTRATED LIGHTING |
JPS5763377A (en) * | 1980-10-03 | 1982-04-16 | Mitsui Toatsu Chem Inc | Liquid crystal composition for color display |
US4378302A (en) * | 1980-12-16 | 1983-03-29 | General Electric Company | Red perylene dichroic dye containing liquid crystal formulations |
JPS581775A (en) * | 1981-06-26 | 1983-01-07 | Mitsubishi Chem Ind Ltd | Liquid crystal composition |
WO1983001103A1 (en) * | 1981-09-17 | 1983-03-31 | Frederick Brian Mckee | Improvement in or relating to windows |
US4561221A (en) * | 1981-09-17 | 1985-12-31 | Mckee Frederick B | Windows |
DE3149620A1 (en) * | 1981-12-15 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | LIGHT COLLECTION SYSTEMS USING HALOGENED PERYLENE DERIVATIVES AS A LIGHT CONVERTER |
DE3236241A1 (en) * | 1982-09-30 | 1984-04-05 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING LIGHT COLLECTORS |
DE3400991A1 (en) * | 1984-01-13 | 1985-07-18 | Basf Ag, 6700 Ludwigshafen | METHOD FOR CONCENTRATING LIGHT AREA AND NEW DYES |
US4597891A (en) * | 1984-06-04 | 1986-07-01 | Polaroid Corporation | Liquid crystal compositions and devices and novel compounds |
JP5976675B2 (en) | 2011-01-05 | 2016-08-24 | 日東電工株式会社 | Wavelength-converting perylene diester chromophore and luminescent film |
US20140311566A1 (en) * | 2011-11-04 | 2014-10-23 | Nitto Denko Corporation | Microstructured wavelength conversion films for enhanced solar harvesting efficiency |
KR101844881B1 (en) | 2011-12-06 | 2018-04-03 | 닛토덴코 가부시키가이샤 | Wavelength conversion material as encapsulate for solar module systems to enhance solar harvesting efficiency |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2139688A1 (en) * | 1971-08-07 | 1973-02-15 | Basf Ag | DYES FOR COLORING PLASTICS |
DE2139690A1 (en) * | 1971-08-07 | 1973-02-15 | Basf Ag | Polychlorperylene-3:4:9:10-tetracarboxylic acid diimides - - prepn by chlorinating corresponding perylene-3:4:9:10-tetracarboxyl |
DE2147024A1 (en) * | 1971-09-21 | 1973-03-29 | Basf Ag | DYES OF THE PERYLENE TETRACARBON ACEUREDIIMIDE SERIES |
DE2210170A1 (en) * | 1972-03-03 | 1973-09-06 | Basf Ag | Fluorescent pigment dye - of the perylene tetracarboxylic acid diimide series,for use in plastics |
DE2451781C2 (en) * | 1974-10-31 | 1976-08-19 | Basf Ag, 6700 Ludwigshafen | Perylene SASMO tetracarboxylic acid bisimide dye |
DE2451784A1 (en) * | 1974-10-31 | 1976-05-13 | Basf Ag | Perylene 3,4,9, 10-tetracarboxylic acid diimide dyes - contg. ether gps., for use in paints, resins, printed inks, plastics etc. |
DE2620115C2 (en) * | 1976-05-06 | 1983-08-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 8000 München | Device for converting light energy into electrical energy |
-
1978
- 1978-11-29 DE DE2851513A patent/DE2851513C3/en not_active Expired - Lifetime
-
1979
- 1979-11-28 JP JP15306879A patent/JPS5575480A/en active Granted
-
1988
- 1988-08-22 JP JP63206503A patent/JPS6485282A/en active Granted
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9382424B2 (en) | 2011-09-26 | 2016-07-05 | Nitto Denko Corporation | Highly-fluorescent and photo-stable chromophores for enhanced solar harvesting efficiency |
US9394479B2 (en) | 2011-10-05 | 2016-07-19 | Nitto Denko Corporation | Wavelength conversion film having pressure sensitive adhesive layer to enhance solar harvesting efficiency |
Also Published As
Publication number | Publication date |
---|---|
JPH0113512B2 (en) | 1989-03-07 |
DE2851513A1 (en) | 1980-06-12 |
JPS5575480A (en) | 1980-06-06 |
DE2851513C2 (en) | 1986-10-30 |
JPH0424397B2 (en) | 1992-04-24 |
JPS6485282A (en) | 1989-03-30 |
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8126 | Change of the secondary classification |
Ipc: G02F 2/00 |
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D2 | Grant after examination | ||
8363 | Opposition against the patent | ||
8380 | Miscellaneous part iii |
Free format text: ES ERFOLGT EIN ERGAENZUNGSDRUCK MIT DEN RICHTIGEN FORMELN I UND III |
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