WO2016198496A1 - Composition comprenant un composé luminescent - Google Patents

Composition comprenant un composé luminescent Download PDF

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Publication number
WO2016198496A1
WO2016198496A1 PCT/EP2016/063103 EP2016063103W WO2016198496A1 WO 2016198496 A1 WO2016198496 A1 WO 2016198496A1 EP 2016063103 W EP2016063103 W EP 2016063103W WO 2016198496 A1 WO2016198496 A1 WO 2016198496A1
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Prior art keywords
composition
recurring units
layer
collector
polymer
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PCT/EP2016/063103
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English (en)
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Elena Molena
Luciano Miozzo
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Solvay Specialty Polymers Italy S.P.A.
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Publication of WO2016198496A1 publication Critical patent/WO2016198496A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18—Homopolymers or copolymers or tetrafluoroethene
    • 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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C09D127/18—Homopolymers or copolymers of tetrafluoroethene
    • 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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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

Definitions

  • the present invention pertains to a composition comprising a semi-crystalline polymer and a luminescent compound, and to a solar concentrator including a collector that comprises such composition.
  • Luminescent solar concentrators operate on the principle of collecting radiation over a large area, converting it by luminescence (commonly using a fluorescent compound) and directing the generated radiation into a smaller area output target.
  • a luminescent solar concentrator typically comprises a luminescent material coupled to or embedded with a material acting as a waveguide to form a radiation collector and at least one photovoltaic cell coupled to said collector.
  • the collector is typically an optically transparent sheet made of a composition comprising a polymer and a luminescent compound. A substantial fraction of incident solar radiation is absorbed by the luminescent compound trapped in the collector and directed via internal reflection to at least one output surface of said collector.
  • the luminescent compound is responsible for conversion of at least a part of the incident solar light into a radiation with a longer wavelength which is advantageous for the silicon cell, which has maximum external quantum efficiency around 1100 nm.
  • the photovoltaic cells coupled to the output surfaces of the collector then convert the emitted electromagnetic radiation into electric current.
  • LSCs comprise parallel thin, flat layers of alternating luminescent and transparent materials, placed to gather incoming radiation on their (broader) faces and emit concentrated radiation around their (narrower) edges. More recently, other configurations were made available, such as doped or coated optical fibers, or contoured stacks of alternating layers.
  • Sheets or layers made from polymers such as polycarbonate and poly(methyl methacrylate) are typically used as waveguides, because of their high optical transparency and high refractive index.
  • US 2009/0126778 (SABIC INNOVATIVE PLASTICS IP B.V.) 5/21/2009 discloses a LSC comprising a primary waveguide and a photovoltaic cell, wherein the primary waveguide is made from a composition comprising a polymer, typically a polycarbonate or an acrylic ester polymer such as poly(methylmethacrylate), and a fluorescent colorant selected from the group consisting of a dye, a pigment and a quantum dot.
  • a polymer typically a polycarbonate or an acrylic ester polymer such as poly(methylmethacrylate)
  • a fluorescent colorant selected from the group consisting of a dye, a pigment and a quantum dot.
  • composition (C) comprising: - at least one semi-crystalline polymer (P) having a heat of fusion of at most 35 J/g and comprising recurring units derived from ethylene and at least one of chlorotrifluoroethylene (CTFE), and tetrafluoroethylene (TFE); - at least one luminescent compound (L), wherein the composition comprises at most 0.5% in weight, with respect to the total weight of the composition, of a polymer formed of recurring units deriving from acrylate monomers (polyacrylate A).
  • a collector for a luminescent solar concentrator comprising at least one portion exposed to radiations (portion (F)) comprising the composition (C) as defined above, and of a luminescent solar concentrator comprising said collector.
  • the present invention achieves these objectives by providing a process for the manufacture of a collector for a luminescent solar concentrator, said process comprising: (i) providing the composition (C) as defined above and (ii) processing into a layer the composition (C) provided in step (i).
  • Figure 1 optical efficiency vs concentration of luminescent compound (L) in the composition of the invention
  • compositions “comprises” one or more component(s) includes the compositions that consist up to 100% of such component(s).
  • a polymer “consists essentially of” one or more recurring unit(s) means that they form at least 95% of the total of the recurring units.
  • polyacrylate indicates a polymer comprising substantially, or consisting of, recurring units derived at least one monomer (H) comprising at least one carboxylic acid ester group of formula -COOM, wherein M is a C 1 -C 5 alkyl group.
  • the polyacrylate (A) is of formula (A-1): wherein M is a C 1 -C 5 alkyl group, R is H or -CH 3 and n is an integer such that the number average molecular weight of the polyacrylate (A) is of from 1000 to 1000000, typically of from 2000 to 100000, more typically of from 3000 to 60000.
  • a typical example of such polyacrylate (A) is polymethylmethacrylate (PMMA).
  • the amount of polyacrylate can be determined via any of the methods known to the person skilled in the art, such as by MALDI MS/MS techniques (e.g. those reported in G. Montaudo et al. Prog. Polym. Sci. 2006 , 31 , 277–357, and references cited therein).
  • the term “luminescent compound [compound (L)]” is intended to denote either a fluorescent compound [compound (L-F)] or a phosphorescent compound [compound (L-P)].
  • the term “luminescent” indicates a compound capable of spontaneous emission of radiation when electronically or vibrationally excited and not in thermal equilibrium with its environment.
  • the compound (L) is able to re-emit an absorbed electromagnetic radiation when passing from an excited state to a ground state.
  • the wavelength of the re-emitted radiation is usually longer that the wavelength of the absorbed radiation.
  • compound (L) is a fluorescent compound, that is a compound that re-emits the radiation essentially only during the irradiation of a substance by an electromagnetic radiation.
  • the choice of the compound (L) is not particularly limited.
  • the compound (L) is typically selected from the group consisting of luminescent organic or inorganic compounds. Mixtures of one or more organic compounds (L) and one or more inorganic compounds may be used in the composition (C) of the invention. In alternative, an luminescent organic compound alone or mixtures of luminescent organic compounds may be separately used.
  • the composition of the invention comprises at least one luminescent compound (L) that is a fluorescent compound.
  • inorganic luminescent compounds (L) include quantum dots or nanoparticles, e.g.
  • CIS CuInS­ 2
  • CdSe/CdS or PbSe/PbS quantum dots BAM (barium magnesium aluminate doped with Europium or other elements), phosphors such as BAM:Ce 2+ ; YAG:Ce 3+ ; (Sr,Ba)SiO 4 :Eu 2+ ; LuAG:Ce 3+ .
  • Non-limiting examples of organic compounds (L) typically include polycyclic aromatic compounds, preferably those comprising a perylene dimiide core (also indicated as bis-diimide of peri-dinaphthalene, perilene or dibenz[ de,kl ]anthracene), linear conjugate systems such as polyparaphenylene/arylene, planar benzofused systems such as rubrene, coumarin dyes and metallorganic compounds containing Ir, B, Al or Pt (for example BODIPY, i.e. boron-dipyrromethene, Alq3, i.e. tris(8-hydroxyquinolinato)aluminium ).
  • a perylene dimiide core also indicated as bis-diimide of peri-dinaphthalene, perilene or dibenz[ de,kl ]anthracene
  • linear conjugate systems such as polyparaphenylene/arylene
  • planar benzofused systems such as rubrene
  • the organic compound (L) is preferably of formula (L-1): wherein: - G 1 is a linear or branched alkyl group or oxygen-containing alkyl group of formula C n H 2n+1 O m , wherein n is an integer of from 1 to 44 and m is lower than n/2, or a group (Y) as depicted above, wherein each of A, B, P, J and Q is independently a hydrogen atom, a fluorine atom, a methoxy group or a C n H 2n+1 alkyl group, wherein n is an integer from 1 to 16, - each of G 2 , G 3 , G 4 and G 5 is independently a hydrogen atom, a fluorine atom, a methoxy group, a C n H 2n+1 alkyl group, wherein n is an integer from 1 to 16, or a group (X) as depicted above, wherein each of D, E, I, L and M is independently a hydrogen atom, a
  • organic compounds (L) of formula (L-1) suitable for use in the composition (C) of the invention are those having the following CAS numbers: 112100-07-9 (1, 6, 7, 12-tetraphenoxyperylene-N, N'-Bis-(2, 6-diisopropylphenyl)-3, 4:9, 10-tetracarboxdiimide, Lumogen F Red® by BASF ); 848841-82-7 (Lumogen Violet 570® by BASF),
  • the luminescent compound (L) in composition (C) of the invention comprises, or consists of, 1, 6, 7, 12-tetraphenoxy perylene-N, N'-Bis-(2, 6-diisopropylphenyl)-3, 4:9, 10-tetracarboxdiimide (CAS number: 112100-07-9), corresponding to the structure wherein in formula (L-1) G 1 is a group (Y), each of G 2 , G 3 , G 4 and G 5 is a group (X), each of A and P is a isopropyl group and each of B, J, D, E, I, L and M is a hydrogen atom.
  • the amount of the at least one luminescent compound (L) in composition (C) is from 0.00005 to 5%, preferably 0.005 to 4%, more preferably from 0.025 to 3% or from 0.05 to 2% or from 0.1 to 1% in weight with respect to the total weight of the composition.
  • luminescent compound (L) in composition (C) is 1, 6, 7, 12-tetraphenoxyperylene-N, N'-Bis-(2, 6-diisopropylphenyl)-3, 4:9, 10-tetracarboxdiimide (CAS number 112100-07-9) in amount from 0.0005 to 3%, preferably 0.005 to 1%, more preferably from 0.025 to 0.75% or from 0.05 to 0.5% in weight with respect to the total weight of the composition.
  • luminescent compound (L) in composition (C) is the perylene compound having CAS number 848841-82-7 (Lumogen Violet 570®) in amount from 0.0005 to 3%, preferably 0.001 to 1%, more preferably from 0.025 to 0.75% or from 0.05 to 0.5% in weight with respect to the total weight of the composition.
  • composition (C) may further comprise one or more additives selected from the group consisting of UV blockers, fillers, lubricating agents, heat stabilizers, anti-static agents, acid scavengers, flame-retardants, smoke-suppressing agents, IR-reflectors, thermal conductive fillers and the like.
  • additives selected from the group consisting of UV blockers, fillers, lubricating agents, heat stabilizers, anti-static agents, acid scavengers, flame-retardants, smoke-suppressing agents, IR-reflectors, thermal conductive fillers and the like.
  • composition (C) may preferably further comprise at least one metal or semi-metal compound in the form of nanoparticles.
  • UV blockers are not particularly limited; both organic and inorganic compounds may be used.
  • Preferred UV blockers are notably based on CeO 2 , ZnO and/or TiO 2 .
  • composition (C) typically comprises: - from 90% to 99.99% by weight over the total weight of (C) of at least one thermoplastic polymer (P), - from 0.01% to 10% by weight over the total weight of (C) of at least one compound (L).
  • the composition (C) preferably comprises: - from 95% to 99.975% by weight, over the total weight of (C), at least one thermoplastic polymer (P), - from 0.025% to 5% by weight, over the total weight of (C), of at least one compound (L), more preferably from 97 to 99.95 of (P) and 3 to 0.05 of (L) in weight over the total weight of (C).
  • the polymer (P) comprises: (a) from 30 to 48%, preferably from 35 to 45 % by moles of recurring units derived from ethylene (E); (b) from 52 to 70%, preferably from 55 to 65%, by moles of recurring units derived from chlorotrifluoroethylene (CTFE) or tetrafluoroethylene (TFE) or mixture thereof; and (c) from 0 to 5%, preferably from 0.5 to 2.5 % by moles of recurring units derived from one or more fluorinated and/or hydrogenated comonomer(s), different from E, CTFE and TFE, wherein all the percentages are with respect to the total number of moles of recurring units in (P).
  • E ethylene
  • CTFE chlorotrifluoroethylene
  • TFE tetrafluoroethylene
  • the polymer (P) is an ECTFE copolymer, said ECTFE copolymer being copolymer of ethylene and CTFE and optionally said third monomer.
  • the polymer (P) may further comprise from 0.1% to 5% by moles, based on the total amount of monomers (a’) and (b’), of recurring units deriving from at least one other monomer selected from the group consisting of fluorinated monomers (F) and hydrogenated monomers (H).
  • Non-limiting examples of monomers (F) suitable for polymers (P) include, notably, monomers (F) selected from the group consisting of perfluoroalkylvinylethers, perfluoroalkylethylenes such as perfluorobutylethylene, perfluorodioxoles and vinylidene fluoride.
  • monomers (F) selected from the group consisting of perfluoroalkylvinylethers, perfluoroalkylethylenes such as perfluorobutylethylene, perfluorodioxoles and vinylidene fluoride.
  • R 2 optionally contains one or more functional groups, preferably selected from the group consisting of OH, COOH, epoxide, ester and ether groups. R 2 may optionally contain double bonds.
  • R 2 is preferably an alkyl group having from 1 to 10 carbon atoms containing hydroxyl functional groups and n is an integer in the range of from 0 to 5.
  • Most preferred monomers (H) suitable for polymers (F-2) are selected from the group consisting of the acrylic monomers of formula (H-2) as defined above.
  • ECTFE polymers free from other monomers are most preferred.
  • the polymer (P) is an ECTFE copolymer and has a melting temperature not exceeding 210°C, preferably not exceeding 200°C, more preferably not exceeding 198°C, more preferably not exceeding 195°C, more preferably not exceeding 193°C, even more preferably not exceeding 190°C, even more preferably not exceeding 180°C.
  • the polymer (P) is an ECTFE copolymer and possesses a melting temperature of advantageously at least 120°C, preferably of at least 130°C, still preferably of at least 140°C, more preferably of at least 145°C, even more preferably of at least 150°C.
  • the melting temperature can be determined, for example, by Differential Scanning Calorimetry (DSC) at a heating rate of 10°C/min, according to ASTM D 3418.
  • the heat of fusion of polymer (P) can be determined by Differential Scanning Calorimetry (DSC) using a method known to the person skilled in the art, e.g. at a heating rate of 10°C/min according to ASTM D 3418.
  • DSC Differential Scanning Calorimetry
  • Polymer (P) possesses a heat of fusion of at most 35 J/g, preferably of at most 30 J/g, more preferably of at most 25 J/g, even more preferably below 20 J/g.
  • polymer (P) is essential for polymer (P) of being a semi-crystalline polymer, i.e. a polymer having a detectable melting point when determined according to ASTM D 3418. Without lower limit for heat of fusion being critical, it is nevertheless understood that polymer (P) will generally possess a heat of fusion of at least 1 J/g, preferably of at least 2 J/g, more preferably of at least 5 J/g, determined according To the aforementioned method.
  • the heat of fusion of polymer (P) in the composition according to the invention is from 30 to 1 J/g, more preferably from 2 to 25 J/g, even more preferably from 5 J/g to 20 J/g (e.g. determined according to ASTM D3418 at a heating rate of 10°C/min).
  • the polymer (P) is an ECTFE copolymer and consists essentially (i.e. by more than 99.9 mole % with respect to the total number of moles of recurring units) of: (a) from 30 to 48%, more preferably 35 to 47%, even more preferably from 38 to 41% by moles, with respect to the total number of moles of recurring units, of recurring units derived from ethylene (E); (b) from 70 to 52%, more preferably 53 to 65%, even more preferably from 62 to 59 by moles, with respect to the total number of moles of recurring units, of recurring units derived from chlorotrifluoroethylene (CTFE).
  • CTFE chlorotrifluoroethylene
  • the amount of polyacrylate polymers in the composition (C) according to the invention is lower than 0.05%, preferably lower than 0.01%, even more preferably lower that 0.001% in weight with respect to the total weight of the composition, i.e. no polyacrylate polymer is detectable in composition (C) .
  • Such amount can be determined by any suitable analytical method known to the person skilled in the art.
  • the substantial absence of polyacrylate in the composition according to the present invention is advantageous, as polyacrylates are subject to radical degradation, particularly upon exposure to solar light and electromagnetic radiations in general, which results in shorter service life of the articles comprising polyacrylates.
  • the amount of semi-crystalline polymer (P) in the composition (C) is at least 95%, preferably 97.5%, more preferably at least 99% in weight with respect to the total weight of the composition.
  • composition according to the present invention is particularly suitable for manufacturing protective films, including films for protecting photovoltaic (PV) modules, in particular for front-sheets or back-sheets of PV cells, but also architectural membranes and films for agricultural purposes.
  • PV photovoltaic
  • thermoplastic fluoropolymer composition (C) as above described, said process comprising mixing : - the polymer (P), as above detailed; and - the luminescent compound (L).
  • said process comprises advantageously mixing by dry blending and/or melt compounding the polymer (P) and the compound (L), as above detailed.
  • the process comprises a first step wherein the polymer (P) is provided under the form of powder and is dry-blended with said compound (L) in the form of particles, optionally under the form of a dispersion of particles in a liquid medium so as to obtain a powder/paste mixture and a second step wherein said powder/paste mixture is melt compounded.
  • polymer (A) and the luminescent compound particles (L) can be directly mixed by melt compounding.
  • the polymer (A) and the luminescent compound (L) particles are melt-compounded in continuous or batch devices. Such devices are well-known to those skilled in the art.
  • thermoplastic fluoropolymer composition of the invention examples include screw extruders.
  • polymer (A) and the luminescent compound (L) particles, and optionally other ingredients are advantageously fed in an extruder and the thermoplastic fluoropolymer composition of the invention is extruded.
  • This operating method can be applied either with a view to manufacturing finished product such as, for instance, hollow bodies, pipes, laminates, calendared articles, or with a view to having available granules containing the desired composition, optionally additives and fillers, in suitable proportions in the form of pellets, which facilitates a subsequent conversion into finished articles.
  • the thermoplastic fluoropolymer composition of the invention is advantageously extruded into strands and the strands are chopped into pellets.
  • the polymer (A) and the luminescent compound particles are melt compounded in single-screw or twin-screw extruder.
  • suitable extruders well-adapted to the process of the invention are those available from Leistritz, Maris America Corp., Werner and Pfleiderer and from Farrel.
  • Still another object of the invention is the use of the thermoplastic fluoropolymer composition as defined above for the manufacturing of films.
  • composition of the invention will be preferably processed under the form of a film by cast extrusion or hot blown extrusion techniques, optionally with mono- or bi-axial orientation.
  • a technique particularly suitable for the manufacture of films of the composition of the invention involves extruding the molten composition through a die having elongated shape so as to obtain an extruded tape and casting/calendering said extruded tape so as to obtain a film.
  • Tape can be calendered into a film by passing through appropriate rolls, which can be maintained at appropriate temperatures, and whose speed can be adjusted so as to achieve the required thickness.
  • Films and layers obtained from the composition of the invention are preferably transparent films and layers, i.e. films and layers having a total transmittance (and/or haze) of more than 80%, preferably more than 85%, even more preferably more than 92 % when determined on films having a thickness of about 50 ⁇ m, when measured according to ASTM D 1003 standard in air.
  • Total transmittance and haze can also be determined according to ASTM D1003 standard in water, e.g. by placing the film in a quartz cuvette filled with deionized water.
  • total transmittance of films and layers obtained from the inventive composition is generally of more than 85%, more preferably of more than 90%, even more preferably of more than 94%.
  • films and layers obtained from the composition of the invention are preferably such that in transmission, the scattering of light, responsible for the reduction of contrast of images viewed through it, is limited.
  • films and layers obtained from the composition of the invention have values of haze of less than 15%, preferably of less than 10%, even more preferably of less than 7%, when determined on films and layers having a thickness of about 50 ⁇ m, when measured according to ASTM D 1003 standard in air.
  • the films and layers obtained from the inventive compositions when haze is measured in water, as above detailed for total transmittance, it is generally preferred for the films and layers obtained from the inventive compositions to possess a haze of less than 12%, more preferably of less than 8%, even more preferably of less than 5%.
  • the film of the invention can be advantageously assembled in a multilayer structure.
  • Multilayer structures comprising the film of the invention are also objects of the present invention.
  • Assemblies which have been found particularly useful to the purposes of the invention are those wherein the film of the invention is assembled with a film made from a composition comprising at least one semi-crystalline polymer comprising recurring units derived from ethylene and at least one of chlorotrifluoroethylene (CTFE) and tetrafluoroethylene (TFE).
  • CTFE chlorotrifluoroethylene
  • TFE tetrafluoroethylene
  • the film as above detailed is assembled with at least one layer made from a composition comprising at least one semi-crystalline polymer comprising recurring units derived from ethylene and at least one of chlorotrifluoroethylene (CTFE) and tetrafluoroethylene (TFE), said polymer having a heat of fusion of more than 35 J/g [polymer (B)].
  • CTFE chlorotrifluoroethylene
  • TFE tetrafluoroethylene
  • the present invention provides a sheet or layer comprising composition (C) as described above, that is suitable to be used as a collector in a luminescent solar concentrator.
  • the present invention provides a luminescent solar concentrator comprising at least one collector comprising composition (C) as described above and at least one photovoltaic cell.
  • composition (C) significantly contributes to increasing the optical efficiency of the luminescent solar concentrator of the invention with respect to an analogue composition comprising a semi-crystalline polymer having a heat of fusion higher than 35 J/g for high geometric gains (A collector / A photovoltaic cell).
  • composition (C) significantly contributes to improving durability and weatherability properties of the collector in the luminescent solar concentrator of the invention with respect to the previously available collectors.
  • the collector of the present invention advantageously shows outstanding optical transparency and haze properties, while successfully exhibiting reduced waveguide losses and thus enhanced optical efficiency for high geometric gains. Also, the collector of the present invention advantageously shows excellent interlayer adhesion properties and mechanical properties and can be suitably used in a luminescent solar concentrator.
  • the composition (C) is typically comprised in the outer layer of the collector that is directly exposed to the incident electromagnetic radiation.
  • the collector may further comprise at least one back layer (layer (B)).
  • back layer layer (layer (B)) is intended to denote the inner layer of the collector, which is not directly exposed to the incident radiation.
  • the collector comprises at least one layer (B)
  • said at least one layer (B) is typically adhered to at least one layer (F) that comprises or consists of composition (C) according to the present invention.
  • the layer (B) is preferably made of either glass or of a composition comprising at least one thermoplastic polymer.
  • the thermoplastic polymer may be the thermoplastic polymer (P) or a different polymer with suitable characteristics.
  • the collector further comprises at least one layer (B)
  • it may also further comprise at least one adhesive layer [layer (Ad1)] between at least one layer (F) and at least one layer (B).
  • the nature of the material constituting the layer (Ad1) is not particularly limited, provided that said layer (Ad1) ensures suitable adhesion between the layer (F) and the layer (B) of the collector.
  • the layer (Ad1) is typically made of at least one polymer such as a thermoplastic polymer.
  • the collector preferably consists of: - at least one layer (F), - optionally, at least one layer (B), and - optionally, between said at least one layer (F) and said at least one layer (B), at least one layer (Ad1).
  • the layer (F) of the collector of the invention typically has a thickness of from 0.01 mm to 1 mm, preferably of from 0.01 mm to 0.5 mm.
  • the layer (F) of the collector of the invention typically has a thickness of from 0.01 mm to 100 mm, preferably of from 0.01 mm to 10 mm.
  • the collector of the invention is typically optically transparent.
  • the term “optically transparent” indicates that the incident electromagnetic radiation is allowed to pass through a material without being scattered or absorbed.
  • the collector of the invention is advantageously optically transparent to incident electromagnetic radiation having a wavelength of from about 250 nm to about 2500 nm, preferably of from about 400 nm to about 800 nm.
  • the collector of the invention preferably has a total transmittance of more than 80%, preferably of more than 85%, more preferably of more than 90%, as measured on a collector having a thickness of about 50 ⁇ m according to ASTM D1003 in air.
  • the collector of the invention preferably has values of Haze of less than 15%, preferably of less than 10%, more preferably of less than 7%, as measured on a collector having a thickness of about 50 ⁇ m according to ASTM D1003 in air.
  • the layer (F) typically has a refractive index n 1 comprised between 1 and 2.
  • the layer (Ad1) when present, typically has a refractive index n 3 comprised between 1 and 2.
  • the collector according to the present invention typically has a refractive index n 4 comprised between 1 and 2.
  • the refractive index can be measured according to any suitable method.
  • the present invention pertains to a luminescent solar concentrator comprising at least one collector including composition (C) as defined above and at least one photovoltaic cell.
  • At least one photovoltaic cell of the luminescent solar concentrator of the invention is typically adhered to at least a portion of the collector.
  • the photovoltaic cell is preferably adhered to at least a portion of the collector by means of at least one adhesive layer [layer (Ad2)].
  • the layer (Ad2) typically has a refractive index n 5 comprised between 1 and 2 and has a refractive index n 5 substantially equal to the refractive index n 4 of the collector.
  • the layer (Ad2) is typically made of at least one polymer such as a thermoplastic polymer.
  • the layer (Ad2) is usually made of a polyurethane polymer (particularly for devices wherein the photovoltaic cells are on the edges of the LSC) or of a EVA (ethyl vinyl acetate) polymer.
  • the photovoltaic cell typically has an absorption surface receiving electromagnetic radiation emitted by the collector.
  • the plane of the absorption surface of at least one photovoltaic cell of the luminescent solar concentrator is substantially parallel to the plane of the layer (F) of at least one collector.
  • the collector of this first embodiment of the invention typically has a thickness of from 0.01 mm to 1 mm, preferably of from 0.05 mm to 0.5 mm.
  • the plane of the absorption surface of at least one photovoltaic cell of the luminescent solar concentrator is substantially perpendicular to the plane of the layer (F) of at least one collector.
  • the photovoltaic cell is placed on the edge of the collector surface.
  • the collector of this second embodiment of the invention typically has a thickness of from 0.01 mm to 100 mm, preferably of from 0.05 mm to 10 mm.
  • the photovoltaic cell of the invention typically comprises at least one semiconductor photoactive layer.
  • semiconductor photoactive layer is intended to indicate a layer endowed with photoelectric conversion property and able to perform photovoltaic conversion.
  • the specific materials used for forming such semiconductor photoactive layer include single crystal silicon semiconductor, non-single crystal silicon semiconductor (e.g.
  • a-Si amorphous silicon
  • a-Si amorphous silicon
  • compound semiconductors and junctions such as CuInSe 2 , CuInS 2 , GaAs, CdS/Cu 2 S, CdS/CdTe, CdS/InP, and CdTe/Cu 2 Te
  • organic semiconductors such as polymers and small ⁇ molecule compounds like polyphenylene vinylene, copper phthalocyanine (a blue or green organic pigment) and carbon fullerenes.
  • the semiconductor photoactive layer formed of either of the above semiconductor is typically either a “pn junction” or a “pin junction” or a Schottky junction.
  • the photovoltaic cell may further comprise at least one optically transparent electroconductive layer.
  • the term “electroconductive layer” is intended to denote an upper-side electrode (i.e. an electrode having a light receiving surface).
  • Specific examples of materials suitable for use in the optically transparent electroconductive layer include In 2 O 3 , SnO 2 , In 2 O 3 -SnO 2 (ITO), ZnO, TiO 2 , Cd 2 SnO 4 , crystalline semiconductor layers doped with a high concentration of an impurity, like notably fluorine-doped tin oxide (SnO 2 :F, or “FTO”), doped zinc oxide (e.g. : ZnO:Al) and flexible organic conductors, like, e.g. carbon nanotube networks embedded in a transparent polymer matrix.
  • the layer may be formed by resistance-heating vapor deposition, sputtering, spraying, chemical vapour deposition (CVD), impurity diffusion, and like methods.
  • CVD chemical vapour deposition
  • impurity diffusion and like methods.
  • typical polymer processing technologies are also available, including laminating, casting, extrusion and the like.
  • a grid-type collecting electrode may be provided on the optically transparent electroconductive layer in order to efficiently collect the generated current.
  • materials suitable for use in the collecting electrode include Ti, Cr, Mo, W, Al, Ag, Ni, Cu, Sn, and alloys thereof, and an electroconductive paste such as a silver paste.
  • the collecting electrode may be formed by sputtering, resistance heating, and CVD employing a mask pattern; metal film deposition and subsequent etching for patterning; direct grid electrode pattern formation by photo-assisted CVD; formation of a negative pattern mask of the grid electrode and subsequent metal plating; printing with electroconductive paste, bonding of metal wires, and like methods.
  • the electroconductive paste generally includes a dispersion of powder of silver, gold, copper, nickel, carbon or the like in a polymeric binder.
  • the polymeric binder includes polyester resins, epoxy resins, acrylic resins, alkyd resins, polyvinyl acetate resins, rubbers, urethane resins, and phenol resins. Otherwise, a wire made of a metal such as Cu may be provided on the transparent conductive layer.
  • the photovoltaic cell may also further comprise at least one electroconductive substrate.
  • the term “electroconductive substrate” is intended to denote a base member for the photovoltaic cell as well as a lower-side electrode.
  • materials thereof include silicon, tantalum, molybdenum, tungsten, stainless steel, aluminium, copper, titanium, carbon sheet, lead-plated steel, and resin films, and ceramics and glass having an electroconductive layer formed thereon.
  • a backside reflection layer may be formed from a metal layer, a metal oxide layer, or a lamination thereof.
  • the metal layer can be formed from Ti, Cr, Mo, W, Al, Ag, Ni, Cu, and the like.
  • the metal oxide layer can be formed from ZnO, TiO 2 , SnO 2 , In 2 O 3 -SnO 2 (ITO), and the like.
  • the metal layer and the metal oxide layer may be formed by resistance heating vapor deposition, electron beam vapor deposition, sputtering, or a similar method.
  • the luminescent solar concentrator is generally equipped with output terminals for extracting photovoltaic current.
  • the output terminals are typically in electric connection with the electroconductive substrate and the collecting electrode, respectively.
  • a metal piece such as a copper tab can be used as output terminal at the electroconductive substrate side, connected to the electroconductive substrate by spot welding or soldering.
  • a metal may be electrically connected to the collecting electrode by means of conductive paste or solder.
  • the present invention provides a process for the manufacture of a collector for a luminescent solar concentrator, said process comprising: (i) providing the composition (C) as described above and (ii) processing into a layer the composition (C) provided in step (i).
  • composition (C) provided in step (i) further comprises at least one organic solvent.
  • the composition (C) is processed into a layer in liquid phase, preferably wherein the composition (C) provided in step (i) is free from organic solvents.
  • the composition (C) is processed into a layer in molten phase.
  • ECTFE-c (comparative polymer) is a commercially available ethylene/chlorotrifluoroethylene (E/CTFE, molar ratio 1:1) copolymer having a melting point (T m2 ) of 242°C and a heat of fusion ( ⁇ H 2f ) of 42 J/g and a MFI of 18 g/10min (275°C/2.16 kg).
  • E/CTFE ethylene/chlorotrifluoroethylene
  • ECTFE 1 (polymer (P) according to the present invention): is a 41/59 mole% E/CTFE copolymer having a melting point (T m2 ) of 180°C, a heat of fusion ( ⁇ H 2f ) of about 18 J/g and a MFI of 1.4 g/10min (230°C/2.16 kg).
  • Luminescent compound (L) is Lumogen F 305 Red ® by BASF.
  • compositions of the invention The polymer, under the form of powder, and the organic luminescent particles were pre-mixed in a rapid mixer equipped with a three-stage paddles mixer so as to obtain a homogeneous powder mixture having required weight ratio between mentioned ingredients. Powder mixture was then processed by extrusion in a double screw conical extruder (Brabender), equipped with 4 temperature zones and a 3 mm 2 holes die. Processing set points were set as follows, for ECTFE-c (Table 1) and ECTFE-1 (Table 2), respectively:
  • Table 1 - ECTFE-c processing conditions Table 0001 T1 (head) T2 T3 T4 230 240 260 270
  • Table 2 - ECTFE-1 processing conditions Table 0002 T1(head) T2 T3 T4 210 220 230 240
  • All LSC devices have been fabricated using bulk plates, made with a (fluoro)polymer, as waveguide.
  • Waveguides were prepared from slabs of (fluoro)polymers, prepared by molding from pellets. Pellets were prepared by extrusion, starting from a powder obtained by mixing the polymer and the luminescent dye. The luminescent dye was used in different concentrations (0.0005 – 0.5 wt. %).
  • the standard dimensions of the plate used for the waveguide were 25x25 mm 2 , 2 mm thick.
  • Each plate was then coupled to one or more mc-Si PV cells so that one or more edges of the waveguide were connected to the photoactive area of one or more PV cells. Bonding was performed by means of a hotmelt thermosoftening polyurethane adhesive (but also other index-matching optically clear bonding media can be used) that was placed on the active face of the PV cell after positioning the PV cell face-up on a 140°C hot-plate. Once softening of the polyurethane film was achieved (approximately 2 min at 140°C), each edge of the LSC glass substrate was pressed onto the adhesive film for about 30 s to ensure a good optical contact with the PV cell. The LSC system was then allowed to cool down to room temperature so that hardening of the polyurethane could be achieved.
  • a hotmelt thermosoftening polyurethane adhesive but also other index-matching optically clear bonding media can be used
  • I-V current-voltage
  • ⁇ LSC (FF ⁇ (I SC /A LSC ) ⁇ V OC )/P IN
  • FF (-) is the fill factor
  • I SC (mA) is the short circuit current
  • V OC (V) is the open circuit voltage extracted from the PV cells attached to the LSC waveguide
  • a LSC (cm 2 ) is the area of the LSC top surface
  • P IN (mW cm -2 ) is the incident solar power density.
  • LSC devices have been subjected to weathering tests with a QUVB apparatus according to the international standard ISO 4892-3 (Light source: type 2 (UVB-313); exposure cycle: Method C (8 h dry, 0.48 W/nm*m 2 at 310 nm, 70°C, 4 h condensation, light off, 50°C))
  • LSC devices were periodically taken out of the weather-o-meter chamber for PV characterization, as described in the next section.
  • Haze values were measured on films of comparable thickness. Thickness values were averaged on 9 different points while Haze values were averaged on three points on the same film.
  • the addition of Lumogen Red to a ECTFE-c film leads to a significant increase (29 x) in haze while only a slight increase (2.85) was measured on ECTFE-1 according to the invention. Since Haze is the property that should be most affected by a bad dispersion of Lumogen, it can be inferred that a suitable dispersion of Lumogen Red is obtained in ECTFE-1 and not in ECTFE-c, having a heat of fusion above 35 J/g. Notably, the suitable dispersion is obtained in the substantial absence of PMMA.
  • the optical efficiency was measured at increasing distance from the cell, i.e. from the photovoltaic cell (PC). As known to the person skilled in the art, apparently small variations in the optical efficiency (e.g. 0.5 % or higher) in this type of measurements actually result in significantly higher overall performance of the luminescent solar concentrator.
  • the optical efficiency of the composition according to the invention (comprising ECTFE-1) at a distance between 3 and 6 cm from the PC is higher than that of the comparative composition (comprising ECTFE-c), which indicates that superior performances in terms of electric current are obtainable using a luminescent solar concentrator according to the invention.

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Abstract

La présente invention concerne une composition comprenant un polymère semicristallin et un composé luminescent, ainsi qu'un concentrateur solaire comportant un collecteur qui comprend une telle composition.
PCT/EP2016/063103 2015-06-09 2016-06-09 Composition comprenant un composé luminescent WO2016198496A1 (fr)

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JP2017214555A (ja) * 2016-05-30 2017-12-07 日本バルカー工業株式会社 パーフルオロエラストマー組成物及びシール材

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EP2578075A1 (fr) * 2010-05-28 2013-04-10 Asahi Glass Company, Limited Film de conversion de longueur d'onde
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Publication number Priority date Publication date Assignee Title
JP2017214555A (ja) * 2016-05-30 2017-12-07 日本バルカー工業株式会社 パーフルオロエラストマー組成物及びシール材
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