WO2022112459A1 - Particule de matériau polymère électroluminescent - Google Patents

Particule de matériau polymère électroluminescent Download PDF

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Publication number
WO2022112459A1
WO2022112459A1 PCT/EP2021/083076 EP2021083076W WO2022112459A1 WO 2022112459 A1 WO2022112459 A1 WO 2022112459A1 EP 2021083076 W EP2021083076 W EP 2021083076W WO 2022112459 A1 WO2022112459 A1 WO 2022112459A1
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Prior art keywords
polymer material
light
material particle
organic light
present
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PCT/EP2021/083076
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English (en)
Inventor
Hiroki Yoshizaki
Hiroshi Okura
Ryota YAMANASHI
Marco Greb
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Merck Patent Gmbh
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Publication of WO2022112459A1 publication Critical patent/WO2022112459A1/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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A01G13/02—Protective coverings for plants; Coverings for the ground; Devices for laying-out or removing coverings
    • A01G13/0231—Tunnels, i.e. protective full coverings for rows of plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A01G13/02—Protective coverings for plants; Coverings for the ground; Devices for laying-out or removing coverings
    • A01G13/0256—Ground coverings
    • A01G13/0268—Mats or sheets, e.g. nets or fabrics
    • A01G13/0275—Films
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G9/00—Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
    • A01G9/14—Greenhouses
    • A01G9/1407—Greenhouses of flexible synthetic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—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 an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • 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
    • C09D125/00—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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/04—Homopolymers or copolymers of styrene
    • C09D125/08—Copolymers of styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/132—Phenols containing keto groups, e.g. benzophenones
    • 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
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes

Definitions

  • the present invention relates to a polymer material particle comprising at least one organic light luminescent material and at least one UV absorbing agent, to a method for preparing said polymer material particle and to uses of said polymer material particle, especially in agriculture. Furthermore, the present invention relates to a composition, a formulation, an optical sheet, an agricultural film, an optical device, a greenhouse, a plant, a container and methods comprising said polymer material particle.
  • WO 2019/020602 A1 and WO 2019/020653 A1 discloses utilizing an inorganic phosphor in agriculture.
  • a polymer material particle with a light conversion and light reflection function that produces optimal blue, red and infrared light a polymer material particle with good light-extraction efficiency in an external/internal environment through controlling the refractive index and light dispersion of an organic light luminescent material or by using an organic light luminescent material; a polymer material particle with improved optical properties such as light scattering, absorbing, refraction and/or reflection ability of an organic light luminescent material; a polymer material particle with superior emission characteristics and high quantum efficiency (EQE) of an organic light luminescent material or by using an organic light luminescent material a polymer material particle which efficiently achieves a uniform and bright outgoing light by effectively absorbing the whole lights from a light source by using an organic light luminescent material a polymer material particle with improved long-term moisture durability, improved water resistance, and improved UV-stability and good light durability of an organic light luminescent material; improved
  • the present invention in one aspect provides for a polymer material particle comprising at least one organic light luminescent material and at least one UV absorbing agent.
  • the present invention in another aspect provides for a method for preparing a polymer material particle of the invention, which includes the steps: (a) preparing a suspension by mixing at least one organic light luminescent material, at least one UV absorbing agent and one or more polymer precursors in a liquid phase; and (b) polymerizing the resulting mixture by applying heat.
  • the present invention relates to a use of the polymer material particle of the present invention in agriculture, in an optical sheet, optical film, optical net, optical fiber, optical nonwoven fabric or optical plate, in a spraying, coating or painting agent, in a Light Emitting Diode, in a solar cell or in a plant cultivation pot.
  • the invention relates to a use of the optical sheet of the present invention, the agricultural film of the present invention, or the optical device of the present invention for agriculture, preferably for greenhouse or for controlling a condition of a living organism in agriculture.
  • the invention relates to a use of the polymer material particle of the present invention, the composition of the present invention, the formulation of the present invention, the optical sheet of the present invention, the agricultural film of the present invention, the optical device of the present invention, or the greenhouse of the present invention for the cultivation of algae, bacteria, and/or plankton, preferably it is photo planktons, preferably for improvement of controlling property of a phytoplankton condition, photosynthetic bacteria and/or alga, preferably acceleration of growth of phytoplankton, photosynthetic bacteria and/or alga; improvement of controlling property of plant condition, preferably controlling of a plant height; controlling of color of fruits; promotion and inhibition of germination; controlling of synthesis of chlorophyll and carotenoids, preferably by blue light; plant growth promotion; adjustment and / or acceleration of flowering time of plants; controlling of production of plant components, such as increasing production amount, controlling of polyphenols content, sugar content, vitamin content of plants; controlling of secondary metabolites, preferably controlling of
  • the invention relates to a plant obtained or obtainable by the method of the present invention, or plankton obtained or obtainable by the method of the present invention, or a bacterium obtained or obtainable by the method of the present invention.
  • the term ’’plant means a multicellular organism in the kingdom Plantae that use photosynthesis to make their own food. Then according to the present invention, the plant can be flowers, vegetables, fruits, grasses, trees and horticultural crops
  • Embodiments of vegetables are stem vegetables, leaves vegetables, flowers vegetables, stalk vegetables, bulb vegetables, seed vegetables (preferably beans), roots vegetables, tubers vegetables, and fruits vegetables.
  • One embodiment of the plant can be Gaillardia, Lettuce, Rucola, Komatsuna (Japanese mustard spinach) or Radish (preferably Gaillardia, Lettuce, or Rucola).
  • light modulating material is a material which can change at least one of physical properties of light.
  • it is selected from pigments, dyes and light luminescent materials including organic and inorganic light luminescent materials.
  • pigments stands for materials that are insoluble in an aqueous solution and changes the color of reflected or transmitted light as the result of wavelength-selective absorption and/or reflection, e.g. Inorganic pigments, organic pigments and inorganic-organic hybrid pigments.
  • dye means colored substances that are soluble in an aqueous solution and changes the color as the result of wavelength-selective absorption of irradiation.
  • luminescent means spontaneous emission of light by a substance not resulting from heat. It is intended to include both, phosphorescent light emission as well as fluorescent light emission.
  • the term “light luminescent material” is a material which can emit either fluorescent light or phosphorescent light.
  • phosphorescent light emission or “phosphorescence” is defined as being a spin prohibition light emission from a triplet state or higher spin state (e.g. quintet) of spin multiplicity (2S+1) > 3, wherein S is the total spin angular momentum (sum of all the electron spins).
  • photon down-conversion is a process which leads to the emission of light at longer wavelength than the excitation wavelength, e.g. by the absorption of one photon leads to the emission of light at longer wavelength.
  • photon up-conversion is a process that leads to the emission of light at shorter wavelength than the excitation wavelength, e.g. by the two- photon absorption (TPA) or Triplet-triplet annihilation (TTA), wherein the mechanisms for photon up-conversion are well known in the art.
  • TPA two- photon absorption
  • TTA Triplet-triplet annihilation
  • organometallic compounds stands for chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, transition metals, lanthanides, actinides, and semimetals.
  • the inorganic light luminescent materials include phosphors as well as semiconductor nanoparticles.
  • a “Phosphor” within the meaning of the present application is a materials which absorbs electromagnetic radiation of a specific wavelength range, preferably blue and/or ultraviolet (UV) electromagnetic radiation and converts the absorbed electromagnetic radiation into electromagnetic radiation having a different wavelength range, preferably visible (VIS) light such as violet, blue, green, yellow, orange, or red light, or the near infrared light (NIR).
  • VIS visible
  • NIR near infrared light
  • UV electromagnetic radiation with a wavelength from 100 nm to 389nm, shorter than that of visible light but longer than X-rays.
  • VIS electromagnetic radiation with a wavelength from 390 nm to 700 nm.
  • NIR electromagnetic radiation with a wavelength from 701 nm to 1,000 nm.
  • the emission of CdSe nanocrystals can be tuned from 660 nm for particles of diameter of around 6.5 nm, to 500 nm for particles of diameter of around 2 nm. Similar behavior can be achieved for other semiconductors when prepared as nanocrystals allowing for broad spectral coverage from the UV (using ZnSe, CdS for example) throughout the visible (using CdSe, InP for example) to the near-IR (using InAs for example).
  • Semiconductor nanoparticles may have an organic ligand on the outermost surface of the nanoparticles.
  • the present invention relates to a polymer material particle which comprises at least one organic light luminescent material and at least one UV absorbing agent.
  • the particle comprises or is comprised of polymerized units of one or more appropriate polymerizable monomeric molecules which form a polymer sphere containing the at least one organic light luminescent material and the at least one UV absorbing agent.
  • Suitable polymerizable monomers for forming a polymer material of the polymer material particle can be selected from various kinds of generally known and/or commercially available polymerizable substances. Especially suitable are polymerizable monomeric molecules which form a transparent polymer.
  • Suitable commercially available organic light luminescent material are Lumogen® F Orange 240; Lumogen® Red 300; Lumogen® Red 305; Lumogen® Violet 570; “MK-2” (2-Cyano-3-[5’”-(9-ethyl-9H-carbazol-3-yl)- 3’,3”,3”’,4-tetra-n-hexyl-[2,2’,5’,2”,5”,2”’]-quarterthiophen-5-yl]acrylic acid); “D102” (5-[[4-[4-(2,2-diphenylethenyl)phenyl]-1 , 2, 3, 3a, 4,8b- hexahydrocyclopent[b]indol-7-yl]methylene]-4-oxo-2-thioxo-3- thiazolidineacetic acid); “D205” (5-[[4-[4-(2,2-diphenylethenyl)phenyl]-
  • said polymer material of the particle is selected from one or more member of the group consisting of polyurethanes, poly(meth)acrylates, poly(butylmethacrylate), ethylene-acrylate copolymer, acrylonitrile- butadiene-styrene copolymer, polyesters, polyacrylonitriles, polyacrylurethanes, polyacrylurethanesilicones, polyfluoroacrylurethanes, polyfluoroacrylates, polyvinylchloride, polystyreneacrylates, polybutyrals, polychlorovinylidenes, melamine resins, phenol resins, epoxy resins, urea resins, unsaturated polyester resins, polycarbonates, polysulfones, polyethers, polyamides, polystyrenes including poly(styrene-co- divinylbenzenes, polyisobutylenes, polyethylene, polyethylene terephthalate, polypropylenes, poly(sty
  • the polymerizable monomer for forming the polymer material has intramoleculary integrated at least one chromophore moiety and at least one polymerizable group or moiety.
  • the particle comprises or is comprised of polymerized units of a polymerizable monomeric organic light luminescent material, which can be derived from the organic light luminescent material described herein and contains at least one polymerizable group or moiety and at least one chromophore moiety.
  • the polymer material of the particle comprises or is comprised of polymerized units of a polymerizable monomeric organic light luminescent material having intramoleculary integrated at least one chromophore moiety and at least one polymerizable group or moiety.
  • This embodiment allows for extending the variety of emitting polymer range.
  • Suitable benzophenones are commercially available and include, but are not limited to: Uvinul ® 3049 (commercially available also under the trading names Benzophenone 6, Cyasorb ® UV 12, NSC 40149, Seesorb 107, UV 49, Uvinul ® 3049, Uvinul ® D 49); Uvinul ® 3050 (commercially available also under the trading names BP 2, Benzophenone 2, Dainsorb P 6, Eversorb ® 51, NSC 38556, SUV 1 , Seesorb 106, Sumisorb 150, T 0118, Uvinul ® D 50); ADEKASTAB 1413 (commercially available also under the trading names ARO 8, Aduvex 248, Advastab ® 46, Anti-UV P, Asahi 1413, BP 12, Benzon OO, Benzophenone 12, C 81, Carstab ® 700, Chemisorb 81, Chimassorb ® 81 , Cyasorb ® 531 , Cyasorb ® UV 531 , Cyasorb
  • the amount of the UV absorbing agent is preferably in the range from 0.1- 10.0 wt.%, related to the total weight of the particle.
  • the polymer material particle further comprises at least one stabilizing agent.
  • the stabilizing agent further improves the photoprotection effect described above.
  • ADKSTAB LA-57 (commercially available also under the trading names ADKSTAB LA-57MP, DN 44, LA 57, Mark LA 57); ADKSTAB LA-63P; ADKSTAB LA-68; ADKSTAB LA-72 (commercially available also under the trading names Antioxidant 292, BASF 292, Chiguard ® 353, Chisorb ® 292, HALPS 292, HALS 4, HS 508, JCK-W-US, LA 72, LA 77ME, LS 292, LS 508, LS 765, Light Stabilizer 292, Light, Stabilizer 765, Lowilite 76, Sanol 292, Sanol LS 292, Sanol LS 508, Sanol LS 765, Songlight 2920LQ, TIN 292, TN 765, Tinuvin ® 292, Tinuvin ® 765, Tinuvin ® 766, UV 55-07051 , UV 765); 770DF (commercially available also under the trading names ADK
  • the polymer material particle of the invention has an average particle size in the range of 1 to 1000 pm, more preferably in the range of 10 to 800 pm, as measureing the longest length of 100 particles each independently by scanning electron microscopy.
  • the particle has an external quantum efficiency (EQE) of 10% or more, preferably it is from 10% to 90%, more preferably from 20% to 80%, further more preferably from 30% to 80%, the most preferably it is from 40% to 80%.
  • EQE external quantum efficiency
  • said suspension in step (a) and (a’) further comprises at least one stabilizing agent, which is more preferably selected from hindered amine light stabilizers.
  • the heat acid-generator is, for example, a salt or ester capable of generating an organic acid.
  • examples thereof include: various aliphatic sulfonic acids and salts thereof; various aliphatic carboxylic acids, such as, citric acid, acetic acid and maleic acid, and salts thereof; various aromatic carboxylic acids, such as, benzoic acid and phthalic acid, and salts thereof; aromatic sulfonic acids and ammonium salts thereof; various amine salts; aromatic diazonium salts; and phosphonic acid and salts thereof.
  • Examples of the preferred heat acid-generators containing sulfonate ions include p-toluenesulfonates, benzenesulfonates, p- dodecylbenzenesulfonates, 1 ,4-naphthalenedisulfonates, and methanesulf
  • Examples of the above heat base-generator include: imidazole derivatives, such as, N-(2-nitrobenzyloxycarbonyl)imidazole, N-(3-nitrobenzyloxy- carbonyl)imidazole, N-(4-nitrobenzyloxycarbonyl)imidazole, N-(5-methyl-2- nitrobenzyloxycarbonyl)imidazole, and N-(4-chloro-2-nitro- benzyloxycarbonyl)imidazole; 1 ,8-diazabicyclo(5,4,0)undecene-7, tertiary amines, quaternary ammonium
  • 2,2' azobis(2- methylvaleronitrile), 2,2‘-azobis(dimethylvaleronitrile), azobisisobutyronitrile or a combination of any of these can be used preferably.
  • X- is preferably a counter ion represented by any of the following formulas:
  • Y is a halogen atom
  • the counter ion examples include: BF 4 _ , (C6Fs) 4 B ⁇ , ((CF 3 ) 2 C 6 H 3 ) 4 B-, PFe-, (CF 3 CF 2 ) 3 PF 3 -, SbFe , (C 6 F 5 ) 4 Ga-, ((CF 3 ) 2 C 6 H 3 ) 4 Ga-, SCN , (CF 3 S02)3C-, (CF 3 S02)2N-, formate ion, acetate ion, trifluoromethanesulfonate ion, nonafluorobutanesulfonate ion, methane- sulfonate ion, butanesulfonate ion, benzenesulfonate ion, p- toluenesulfonate ion, and sulfonate ion.
  • those generating sulfonic acids or boric acids are particularly preferred.
  • examples thereof include tricumyliodonium teterakis(pentafluorophenyl)- borate (PFIOTOINITIATOR2074 [trademark], manufactured by Rhodorsil), diphenyliodonium tetra(perfluorophenyl)borate, and a compound having sulfonium ion and pentafluoroborate ion as the cation and anion moieties, respectively.
  • examples of the photo acid-generators also include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium camphor- sulfonate, triphenylsulfonium tetra(perfluorophenyl)borate, 4- acetoxyphenyldimethylsulfonium hexafluoroarsenate, 1-(4-n- butoxynaphthalene-1-yl)tetrahydrothiophenium trifluoromethanesulfonate,
  • each A is independently a substituent group selected from the group consisting of an alkyl group of 1 to 20 carbon atoms, an alkoxy group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an alkylcarbonyl group of 1 to 20 carbon atoms, an arylcarbonyl group of 6 to 20 carbon atoms, hydroxyl group, and amino group; each p 2 is independently an integer of 0 to 5; and B is a fluorinated alkylsulfonate group, a fluorinated arylsulfonate group, a fluorinated alkylborate group, an alkylsulfonate group or an arylsulfonate group.
  • photo acid-generators in which the cations and anions in the above formulas have exchanged each other or combined with various other cations and anions described above.
  • any one of the sulfonium ions represented by the above formulas can be combined with tetra(perfluorophenyl)borate ion, and also any one of the iodonium ions represented by the above formulas can be combined with tetra(perfluorophenyl)borate ion.
  • Those can be still also employed as the photo acid-generators.
  • photo radical-generator examples include azo compounds, peroxides, acyl phosphine oxides, alkyl phenons, oxime esters, and titanocenes.
  • Examples of the photo base-generator include multi-substituted amide compounds having amide groups, lactams, imide compounds, and compounds having those structures.
  • the present invention also relates to a use of the polymer material particle of the present invention in agriculture.
  • the present invention also relates to a use of the polymer material particle of the present invention in an optical sheet, an optical film, an optical net, an optical fiber, an optical nonwoven fabric or an optical plate.
  • the present invention also relates to a use of the polymer material particle of the present invention in a spraying agent, a coating agent or a painting agent.
  • the present invention relates to a use of the polymer material particle of the present invention in a Light Emitting Diode, in a solar cell or in a plant cultivation pot.
  • the present invention also relates to a composition
  • a composition comprising, essentially consisting of, or consisting of, at least one polymer material particle of the present invention and a further material.
  • the further material is a matrix material and said composition can optionally comprises one or more additives selected from one or more members of the group consisting of light modulating materials such as dyes, for example blue or red dyes, pigments, light luminescent materials including organic and inorganic light luminescent materials, for example another organic light luminescent material or inorganic phosphors; photo initiators; co-polymerizable monomers; cross linkable monomers; bromine-containing monomers; sulfur-containing monomers; adjuvants; adhesives; insecticides; insect attractants; metal oxides; Al, Ag, Au nanoparticles; dispersants; surfactants; fungicides and antimicrobial agents.
  • light modulating materials such as dyes, for example blue or red dyes, pigments, light luminescent materials including organic and inorganic light luminescent materials, for example another organic light luminescent material or inorganic phosphors
  • photo initiators co-polymerizable monomers; cross linkable monomers; bromine-containing monomers; sulfur-
  • the matrix material has a weight average molecular weight in the range from 5,000 to 50,000 preferably, more preferably from 10,000 to 30,000.
  • thermosetting polymer publicly known transparent thermosetting polymer can be used preferably.
  • OE6550 (trade mark) series Dow Corning
  • thermoplastic polymers may be copolymerized if necessary.
  • the phosphor is a fluorescent or a phosphorescent inorganic material which contains one or more light emitting centers (i.e. , a so called “inorganic phosphor”).
  • the light emitting centers are formed by activator elements such as e.g. atoms or ions of rare earth metal elements, for example La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er,
  • Tm, Yb and Lu and/or atoms or ions of transition metal elements, for example Cr, Mn, Fe, Co, Ni, Cu, Ag, Au and Zn, and/or atoms or ions of main group metal elements, for example Na, Tl, Sn, Pb, Sb and Bi.
  • suitable phosphors include phosphors based on garnet, silicate, orthosilicate, thiogallate, sulfide, nitride, silicon-based oxynitride, nitridosilicate, nitridoaluminumsilicate, oxonitridosilicate, oxonitridoaluminumsilicate and rare earth doped SiAION.
  • the inorganic phosphor is selected from the group consisting of AI 2 0 3 :Cr 3+ , Y 3 AI 5 0i2:Cr 3+ , MgO:Cr 3+ , ZnGa 2 0 4 :Cr 3+ , MgAI 2 0 4 :Cr 3+ , Gd 3 Ga 5 0i 2 :Cr 3+ , LiAI 5 0 8 :Cr 3+ , MgSr 3 Si 2 0 8 :Eu 2+ ,Mn 2+ , Sr 3 MgSi 2 0s:Mn 4+ , Sr 2 MgSi 2 07:Mn 4+ , SrMgSi 2 06:Mn 4+ , BaMg6Ti60i9:Mn 4+ , Cai 4 AhoZn60 35 :Mn 4+ , Mg 8 Ge 2 0nF 2 :Mn 4+ , Mg 2 Ti0 4 :Mn 4+ ,
  • any type of publicly known materials for example as described in the second chapter of Phosphor handbook (Yen, Shinoya, Yamamoto), can be used if desired.
  • the blue light especially around 450 nm wavelength light may lead to better plant growth, if it is combined with emission light from the organic light luminescent material having the peak wavelength of light emitted from the organic light luminescent material in the range from 600 nm to 820 nm, especially the combination of the blue light around 450 nm wavelength and emission light from the organic light luminescent material having the peak wavelength of light emitted from the organic light luminescent material in the range from 690 nm to 790 nm is preferable for better plant growth.
  • the crosslinkable monomer is selected from the group consisting of tri-methylol-propane tri (meth)acrylate, di-pentaerythritol tetra-(meth)acrylate, di-pentaerythritol hexa-(meth)acrylate, bisphenol-A polyoxyethylene dimethacrylate and a combination thereof.
  • the vinyl monomers and the crosslinkable monomers described above can be used alone or in combination.
  • the invention relates to use of the polymer material particle of the present invention, or the composition of the present invention, or the formulation of the present invention, in a method for preparing an optical sheet or in agriculture, preferably for preparing an agricultural sheet or for controlling a condition of a living organism.
  • Fabrication method for coating of optical sheet by the light reflecting material is not particularly limited. Publicly known methods such as vacuum deposition, sputtering, chemical vapor deposition, printing can be used.
  • the concentration of the polymer material particle of the present invention in the sheet varies from a high concentration on one side of the sheet to a low concentration of the opposite side of the sheet, preferably it is varying from a high concentration on one side of the sheet to a low concentration of the opposite side of the sheet in-plane direction.
  • step (B’) fixing the matrix material by evaporating a solvent of the formulation and/or by polymerizing the composition by applying heat or by exposing the composition under ray of light to thereby form the agricultural film on the surface of the agricultural material
  • the composition or the formulation in step (A’) is provided by immersion coating, gravure coating, roll coating, bar coating, brush coating, spray coating, doctor coating, flow coating, spin coating, slit coating, or by painting.
  • composition comprising at least one polymer material particle according to any one of embodiments 1 to 17 and a further material, preferably selected from one or more members of the group consisting of matrix materials; light modulating materials such as dyes, for example blue or red dyes, pigments, light luminescent materials including organic and inorganic light luminescent materials, for example another organic light luminescent material or an inorganic phosphor; photo initiators; co- polymerizable monomers; cross linkable monomers; bromine-containing monomers; sulfur-containing monomers; adjuvants; adhesives; insecticides; insect attractants; metal oxides; Al, Ag, Au nanoparticles; dispersants; surfactants; fungicides and antimicrobial agents. 21.
  • light modulating materials such as dyes, for example blue or red dyes, pigments, light luminescent materials including organic and inorganic light luminescent materials, for example another organic light luminescent material or an inorganic phosphor
  • photo initiators co- polymerizable monomers; cross linkable mono
  • composition according to embodiment 20, wherein the total amount of the polymer material particle of the composition is in the range from 0.01 wt.% to 10 wt.% based on the total amount of the composition, preferably it is from 0.05 wt.% to 5 wt.%, more preferably from 0.05 wt.% to 3 wt.%, furthermore preferably it is from 0.1 wt.% to 1 wt.%. 22.
  • Optical device comprising at least one optical sheet according to embodiment 25, preferably said optical device is a lighting device, more preferably it is a Light Emitting Diode.
  • optical sheet according to embodiment 25 Use of the optical sheet according to embodiment 25, the agricultural film according to embodiment 28, or the optical device of embodiment 30 for agriculture, preferably for greenhouse or for controlling a condition of a living organism in agriculture.
  • a greenhouse comprising the optical sheet according to embodiment 25, the agricultural film according to embodiment 28, or the optical device of embodiment 30.
  • Method for modulating a condition of a plant, plankton, and/or a bacterium comprising at least following step of providing the optical sheet according to embodiment 25 or the agricultural film according to embodiment 28 between a light source and a plant, between a light source and plankton, preferably said plankton is phytoplankton, between a light source and a bacterium, preferably said bacterium is a photosynthetic bacterium, and/or providing the optical sheet according to embodiment 25 or the agricultural film according to embodiment 28 over a ridge in a field or over a surface of planter, preferably said planter is a nutrient film technique hydroponics system or a deep flow technique hydroponics system to control plant growth.
  • a container comprising at least one plant, plankton, and/or a bacterium according to embodiment 38
  • Technical effects
  • a polymer material particle with a light conversion and light reflection function that produces optimal blue, red and infrared light a polymer material particle with good light-extraction efficiency in an external/internal environment through controlling the refractive index and light dispersion of an organic light luminescent material or by using an organic light luminescent material; a polymer material particle with improved optical properties such as light scattering, absorbing, refraction and/or reflection ability of an organic light luminescent material; a polymer material particle with superior emission characteristics and high quantum efficiency (EQE) of an organic light luminescent material or by using an organic light luminescent material a polymer material particle which efficiently achieves a uniform and bright outgoing light by effectively absorbing the whole lights from a light source by using an organic light luminescent material a polymer material particle with improved long-term moisture durability, improved water resistance, and improved UV-stability and good light durability of an organic light luminescent material; improved dispersibility of polymer material particles and organic light luminescent material in a formulation, composition and/or in
  • microparticles are formed, which are collected from the suspension by aspirator filtration, then are washed with 500 mL of distilled water, 500 mL of ethanol (Sigma-Aldrich) and diethylether (Sigma-Aldrich) in this order. Then, the washed particles are dried in an oven at 50 °C under vacuum for 2 h. 9.46 g of polymer material particles are obtained as illustrated in Figs. 1a and 1b (average diameter: 40 pm; determined by scanning electron microscopy (SEM; Hitachi S- 5200)). Workinq Example 2: Preparation of particle dispersed film
  • 1 g of polymer material particles obtained from working example 1 are dispersed in 10 g of silicone agents mixture (5g of KE-109E-A and 5g of KE-109E-B; Shin-Etsu Chemical) with revolving/rotating mixer (stirring at 2000 rpm for 1 min. and deforming at 2200 rpm for 30 sec.).
  • silicone agents mixture 5g of KE-109E-A and 5g of KE-109E-B; Shin-Etsu Chemical
  • the resulting mixture is applied on a glass plate, and the silicone mixture is cured at room temperature overnight. After curing, the cured silicone film is peeled off.
  • Working Example 3 Film durability check (1) The silicone film prepared as described in working example 2 is irradiated with sunlight for 1 week. After irradiation of sunlight, the film is checked for the change of transmitted light by a solar simulator.

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Abstract

La présente invention concerne une particule de matériau polymère comprenant au moins un matériau électroluminescent organique et au moins un agent absorbant les UV.
PCT/EP2021/083076 2020-11-30 2021-11-26 Particule de matériau polymère électroluminescent WO2022112459A1 (fr)

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EP20210756 2020-11-30

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01103658A (ja) 1987-07-16 1989-04-20 Takeda Chem Ind Ltd ポリカーボネート樹脂組成物
EP2135737A1 (fr) * 2007-04-06 2009-12-23 Asahi Glass Company, Limited Film de conversion de longueur d'onde, film pour usage agricole, structure et composition de formation de film de revêtement
WO2010023115A1 (fr) * 2008-08-28 2010-03-04 Basf Se Stabilisants pour matières organiques inertes
WO2016112200A1 (fr) * 2015-01-07 2016-07-14 Nitto Denko Corporation Films de conversion de longueur d'onde pour régulation thermique incorporant des matériaux à changement de phase
DE102015014526A1 (de) * 2015-11-11 2017-05-11 Giesecke & Devrient Gmbh Sicherheitspigment, lumineszierendes Polymerharz und Verfahren zum Herstellen desselben
JP2017195825A (ja) 2016-04-27 2017-11-02 Jsr株式会社 波長変換フィルム及び農作物の栽培方法
WO2019020653A1 (fr) 2017-07-26 2019-01-31 Merck Patent Gmbh Composition
WO2019020602A2 (fr) 2017-07-26 2019-01-31 Merck Patent Gmbh Luminophore et composition

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01103658A (ja) 1987-07-16 1989-04-20 Takeda Chem Ind Ltd ポリカーボネート樹脂組成物
EP2135737A1 (fr) * 2007-04-06 2009-12-23 Asahi Glass Company, Limited Film de conversion de longueur d'onde, film pour usage agricole, structure et composition de formation de film de revêtement
WO2010023115A1 (fr) * 2008-08-28 2010-03-04 Basf Se Stabilisants pour matières organiques inertes
WO2016112200A1 (fr) * 2015-01-07 2016-07-14 Nitto Denko Corporation Films de conversion de longueur d'onde pour régulation thermique incorporant des matériaux à changement de phase
DE102015014526A1 (de) * 2015-11-11 2017-05-11 Giesecke & Devrient Gmbh Sicherheitspigment, lumineszierendes Polymerharz und Verfahren zum Herstellen desselben
JP2017195825A (ja) 2016-04-27 2017-11-02 Jsr株式会社 波長変換フィルム及び農作物の栽培方法
WO2019020653A1 (fr) 2017-07-26 2019-01-31 Merck Patent Gmbh Composition
WO2019020602A2 (fr) 2017-07-26 2019-01-31 Merck Patent Gmbh Luminophore et composition

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