CN118184646A - Pyrazoline derivative light conversion material for photovoltaic adhesive film, and preparation method and application thereof - Google Patents
Pyrazoline derivative light conversion material for photovoltaic adhesive film, and preparation method and application thereof Download PDFInfo
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- CN118184646A CN118184646A CN202410593694.8A CN202410593694A CN118184646A CN 118184646 A CN118184646 A CN 118184646A CN 202410593694 A CN202410593694 A CN 202410593694A CN 118184646 A CN118184646 A CN 118184646A
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- China
- Prior art keywords
- light conversion
- photovoltaic
- conversion material
- preparation
- pyrazoline derivative
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 73
- 239000000463 material Substances 0.000 title claims abstract description 64
- 150000003219 pyrazolines Chemical class 0.000 title claims abstract description 35
- 239000002313 adhesive film Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 14
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 239000012043 crude product Substances 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- JYSUYJCLUODSLN-UHFFFAOYSA-N 1,3-benzothiazol-2-ylhydrazine Chemical compound C1=CC=C2SC(NN)=NC2=C1 JYSUYJCLUODSLN-UHFFFAOYSA-N 0.000 claims abstract description 7
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims abstract description 7
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011259 mixed solution Substances 0.000 claims abstract description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 32
- 239000012752 auxiliary agent Substances 0.000 claims description 15
- 239000007822 coupling agent Substances 0.000 claims description 14
- 230000003712 anti-aging effect Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000005266 casting Methods 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002978 peroxides Chemical group 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000012528 membrane Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 12
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 pyrazoline compound Chemical class 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000010345 tape casting Methods 0.000 description 4
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 3
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000005282 brightening Methods 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/08—Copolymers of ethene
- C09J123/0807—Copolymers of ethene with unsaturated hydrocarbons only containing more than three carbon atoms
- C09J123/0815—Copolymers of ethene with aliphatic 1-olefins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/08—Copolymers of ethene
- C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C09J123/0853—Vinylacetate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- 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
-
- 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
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
-
- 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/322—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of solar panels
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Electromagnetism (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
Abstract
The invention provides a pyrazoline derivative light conversion material for a photovoltaic adhesive film, and a preparation method and application thereof, and belongs to the technical field of light conversion materials. The preparation method comprises the following steps: (1) Adding a mixed solution of anhydrous potassium carbonate and DMF into a mixture of 5-bromosalicylaldehyde and 1-bromoalkyl, reacting overnight under the protection of nitrogen, filtering after the reaction is finished, evaporating DMF, and purifying a crude product to obtain an intermediate 1; (2) Adding a mixed solution of ethanol and sodium hydroxide into a mixture of 4-bromoacetophenone and the intermediate 1, and reacting at normal temperature to obtain an intermediate 2; (3) And mixing the intermediate 2, 2-hydrazino benzothiazole and ethylene glycol monoethyl ether, and heating and refluxing under the protection of nitrogen to obtain the pyrazoline derivative light conversion material. The light conversion material can be applied to a photovoltaic adhesive film, and the preparation method can be used for obtaining the light conversion material with higher quantum efficiency and improving the light conversion efficiency of a solar cell.
Description
Technical Field
The invention belongs to the technical field of light conversion materials, and particularly relates to a pyrazoline derivative light conversion material for a photovoltaic adhesive film, and a preparation method and application thereof.
Background
Solar light available for solar cells has a wavelength range of 300nm to 1100nm, however, ultraviolet rays (220-400 nm) are harmful to the solar cells, can accelerate the aging of the solar cells, reduce the conversion efficiency of the solar cells, and have higher destructiveness especially for new generation heterojunction and perovskite cells, thereby greatly limiting the application and popularization of the heterojunction and perovskite cells. Therefore, recently, when the solar cell is packaged, the light conversion agent is introduced into the adhesive film, so that the ultraviolet light with the wavelength of 220-400nm can be absorbed, the ultraviolet light can be blocked, and the ultraviolet light can be converted into visible light such as red, green and blue, thereby ensuring that the service life of the solar cell panel can reach more than 20 years, and simultaneously solving the problem that the light conversion efficiency is reduced because the ultraviolet light is blocked.
Pyrazoline is a traditional Chinese medicine five-membered heterocyclic compound with wide application, and the biological activity of some pyrazoline is discovered at present, such as antibiosis, antivirus, fungicidal, immunity inhibition, mollusc killing and the like. The 1,3, 5-triaryl-2-pyrazoline has good fluorescence yield and blue light luminescence characteristic, and can be used as fluorescent brightening agent, dye, fluorescent probe, electroluminescent device and photo-activated herbicide active agent for textiles.
There are also reports of pyrazoline derivatives as fluorescent probe molecules. Such as: the compound I realizes the logic on or off of Hg 2+ by utilizing the coordination action of three nitrogen atoms on pyridine and pyrazole rings; kazuyuki Kasuga the synthesized compound II provides a bidentate ligand with two nitrogen atoms on pyrazole and pyridine, acts with Zn 2+ at 2:1, selectively fluorescence enhanced and red shifted.
However, there are few reports on the use of pyrazoline derivatives as light conversion materials in photovoltaic films, and patent publication No. CN 106470988A discloses a novel pyrazoline compound, a photoelectric conversion element and a solar cell using the same, wherein the photoelectric conversion element and the solar cell using the pyrazoline compound have the characteristics of high conversion efficiency and low cost.
However, the existing pyrazoline compounds cannot well absorb ultraviolet light to protect the solar cell, emit light with a wavelength greater than 400nm for the solar cell, and have poor light conversion efficiency, so that it is necessary to provide a light conversion material with high quantum efficiency, which can absorb ultraviolet light to protect the solar cell, emit light with a wavelength greater than 400nm for the solar cell, and can improve the light conversion efficiency of the solar cell.
Disclosure of Invention
Based on the problems existing in the prior art, the invention aims to provide a pyrazoline derivative light conversion material for a photovoltaic adhesive film, and a preparation method and application thereof. The light conversion material can be applied to a photovoltaic adhesive film, and the preparation method can be used for obtaining the light conversion material with higher quantum efficiency and improving the light conversion efficiency of a solar cell.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
in one aspect, the invention provides a preparation method of a pyrazoline derivative light conversion material for a photovoltaic adhesive film, which comprises the following steps:
The first step: adding a mixed solution of anhydrous potassium carbonate and DMF into a mixture of 5-bromosalicylaldehyde and 1-bromoalkyl, reacting overnight under the protection of nitrogen, filtering after the reaction is finished, evaporating DMF, and purifying a crude product to obtain an intermediate 1;
And a second step of: adding a mixed solution of ethanol and sodium hydroxide into a mixture of 4-bromoacetophenone and the intermediate 1, reacting at normal temperature, filtering after the reaction is finished, washing, and recrystallizing a crude product to obtain an intermediate 2;
And a third step of: and mixing the intermediate 2, 2-hydrazino benzothiazole and ethylene glycol monoethyl ether, heating and refluxing under the protection of nitrogen, filtering after the reaction is finished, and recrystallizing a crude product to obtain the pyrazoline derivative light conversion material.
Wherein,
The 1-bromoalkyl group in the first step is a 1-bromoC 1-12 alkyl group, preferably 1-bromohexane or 1-bromododecane.
The mol ratio of the 5-bromosalicylaldehyde to the 1-bromoalkyl in the first step is 1:1;
The volume ratio of the anhydrous potassium carbonate to the DMF in the first step is 1:6-10;
the reaction temperature in the first step is 70-150 ℃;
the purification in the first step is purification by column chromatography.
The molar ratio of the 4-bromoacetophenone to the intermediate 1 in the second step is 1:1;
The volume ratio of the sodium hydroxide to the ethanol in the second step is 1:8-10;
The concentration of sodium hydroxide in the second step is 30%;
the reaction time in the second step is 1-4h;
the recrystallization in the second step is recrystallization using ethanol.
The mol ratio of the intermediate 2, the 2-hydrazino benzothiazole and the ethylene glycol monoethyl ether in the third step is 1:1:32;
the reflux time in the third step is 1-4h;
the recrystallization in the third step is recrystallization using absolute ethanol.
On the other hand, the invention also provides a pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the method.
In still another aspect, the invention further provides an application of the pyrazoline derivative light conversion material for the photovoltaic film, which is prepared by the method, in a photovoltaic device or a solar cell.
In still another aspect, the invention also provides a photovoltaic adhesive film, which comprises 0.05-0.2 part of pyrazoline derivative light conversion material, 100 parts of resin, 0.4-1 part of main cross-linking agent, 0.3-1 part of auxiliary cross-linking agent, 0.1-0.5 part of coupling agent and 0.05-0.4 part of anti-aging auxiliary agent, wherein the pyrazoline derivative light conversion material is prepared by the preparation method.
The resin is selected from EVA and/or POE;
the main crosslinking agent is a peroxide crosslinking agent;
The peroxide cross-linking agent is at least one selected from tert-butyl peroxy 2-ethylhexyl carbonate, tert-amyl peroxy (2-ethylhexyl) carbonate, dicumyl peroxide, 1-bis (tert-butylperoxy) -3, 5-trimethylcyclohexane and polyether poly-tert-butyl peroxycarbonate.
The auxiliary crosslinking agent is an allyl crosslinking agent;
The allyl cross-linking agent is at least one selected from triallyl isocyanurate, trimethylallyl isocyanate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate and propoxylated trimethylolpropane triacrylate.
The coupling agent is a silane coupling agent,
The coupling agent is at least one selected from vinyl silane coupling agent, amino silane coupling agent, isocyanate group silane coupling agent, sulfur-containing silane coupling agent, epoxy silane coupling agent and phthalate ester coupling agent.
The anti-aging auxiliary agent is one or more selected from an antioxidant, a stabilizer, an ultraviolet cut-off agent, a hydrolysis resistance auxiliary agent and a metal ion capturing agent.
In still another aspect, the present invention also provides a method for preparing a photovoltaic film comprising a pyrazoline derivative light conversion material, comprising the steps of:
(1) Uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method, with an auxiliary agent to obtain a mixture 1;
(2) Spraying the mixture 1 obtained in the step (1) onto resin particles, and fully stirring to obtain a mixture 2;
(3) And (3) casting the mixture 2 into a film by a casting machine to obtain the photovoltaic adhesive film.
The stirring temperature in the step (2) is 30-50 ℃ and the stirring time is 2-6h.
The temperature of the cast film in the step (3) is 60-100 DEG C
Compared with the prior art, the invention has the beneficial effects that:
The pyrazoline compound provided by the invention can well absorb ultraviolet light to protect the solar cell, and simultaneously emit light with the wavelength of more than 400nm for the solar cell, and the light conversion efficiency of the solar cell is high.
Drawings
FIG. 1 is a graph of the ultraviolet and fluorescence properties of material A;
FIG. 2 is a graph of the ultraviolet and fluorescence properties of material B;
FIG. 3 is a graph of the ultraviolet and fluorescence properties of material C;
FIG. 4 is a graph of the ultraviolet and fluorescence properties of material D;
FIG. 5 is a graph of the ultraviolet and fluorescence properties of material E;
FIG. 6 is a hydrogen spectrum of material A prepared in example 1;
FIG. 7 is a hydrogen spectrum of material B prepared in example 1.
Detailed Description
The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described are some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1a method for preparing pyrazoline derivative light conversion material for photovoltaic film:
The method comprises the following steps:
synthesis of intermediate 1 in the first step: 5-bromine salicylaldehyde and 1-bromohexane are added according to a volume ratio of 1:1: 7, under the protection of nitrogen, heating to 80-130 ℃ for reaction for 12 hours, filtering after the reaction is finished, removing the solvent DMF by rotary evaporation, and purifying the crude product by column chromatography to obtain an intermediate 1 with the yield of 75%.
Synthesis of intermediate 2 in the second step: feeding 4-bromoacetophenone and an intermediate 1 according to a volume ratio of 1:1, wherein the volume ratio is 1:10 in 30% sodium hydroxide solution and ethanol, stirring at room temperature for 1 to 4 hours, and filtering. After washing the filter cake with water and methanol in this order, the crude product was recrystallized from ethanol and filtered to give intermediate 2 in 80% yield.
And thirdly, synthesizing a material A: adding intermediate 2 and 2-hydrazinobenzothiazole and ethylene glycol monoethyl ether according to the mol ratio of 1:1:32, heating and refluxing for 1 to 4 hours under the protection of nitrogen, filtering, recrystallizing a filter cake by absolute ethyl alcohol, and filtering to obtain a material A with the yield of 71 percent.
The structural formula of the material A is as follows:
Example 2a method for preparing pyrazoline derivative light conversion material for photovoltaic film:
The method comprises the following steps:
Synthesis of intermediate 1 in the first step: 5-bromosalicylaldehyde and 1-bromododecane are added according to a ratio of 1:1, and the product ratio is 1:7, heating the mixed solution of anhydrous potassium carbonate and solvent DMF under the protection of nitrogen to the temperature ranging from 80 ℃ to 130 ℃ for reaction for 12 hours, filtering after the reaction is finished, removing the solvent DMF by rotary evaporation, and purifying the crude product by column chromatography to obtain the intermediate 1 with the yield of 78%.
Synthesis of intermediate 2 in the second step: 4-bromoacetophenone and an intermediate 1 are added according to the volume ratio of 1:1: 10 in 30% sodium hydroxide solution and ethanol, vigorously stirred at room temperature for 1 to 4 hours, and filtered. The filter cake was washed with water and methanol in this order, and the crude product was recrystallized from ethanol and filtered to give intermediate 2 in 83% yield.
And thirdly, synthesizing a material B: intermediate 2, 2-hydrazino benzothiazole and ethylene glycol monoethyl ether are fed according to a molar ratio of 1:1:32, heated and refluxed for 1 to 4 hours under the protection of nitrogen, filtered, and the filter cake is recrystallized by absolute ethyl alcohol, and filtered to obtain material B, wherein the yield is 85%.
The structural formula of the material B is as follows:
as can be seen from fig. 1 and 2:
The absorption of the material A and the material B is better in the wavelength of 400nm, and simultaneously, under the excitation light of ultraviolet wavelength, the two materials have better fluorescence and luminescence phenomena beyond the wavelength of 400 nm.
Comparative example 1
The difference from example 1 is that: in the first step: the molar ratio of 5-bromosalicylaldehyde to 1-bromohexane was 1:2, and the other steps and operations were the same as in example 1, to finally obtain material C.
Comparative example 2
The difference from example 1 is that: in the first step: the reaction temperature was 160℃and the other steps and operations were the same as in example 1, to finally obtain material D.
Comparative example 3
The difference from example 1 is that: in the first step: the volume ratio of anhydrous potassium carbonate to DMF was 1:5, and the other steps and operations were the same as in example 1, finally obtaining material E.
Application example 1a method for preparing photovoltaic film comprising pyrazoline derivative light conversion material:
comprises the following components: 0.1 part of pyrazoline derivative light conversion material, 100 parts of resin, 0.4 part of main cross-linking agent, 0.3 part of auxiliary cross-linking agent, 0.1 part of coupling agent and 0.05 part of anti-aging auxiliary agent.
The resin is selected from EVA;
the main cross-linking agent is tert-butyl peroxy-2-ethylhexyl carbonate.
The co-crosslinking agent triallyl isocyanurate.
The coupling agent is vinyl silane coupling agent.
The anti-aging auxiliary agent is an antioxidant.
The preparation method comprises the following steps:
(1) Uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of the embodiment 1, a main crosslinking agent, an auxiliary crosslinking agent, a coupling agent and an anti-aging auxiliary agent to obtain a mixture 1;
(2) Spraying the mixture 1 obtained in the step (1) onto EVA particles, and fully stirring for 6 hours at the temperature of 30 ℃ to obtain a mixture 2;
(3) And (3) carrying out tape casting on the mixture 2 by a tape casting machine at the temperature of 60 ℃ to form a film, thus obtaining the photovoltaic adhesive film.
Application example 2a method for preparing photovoltaic film comprising pyrazoline derivative light conversion material:
comprises the following components: 0.1 part of pyrazoline derivative light conversion material, 100 parts of resin, 1 part of main cross-linking agent, 1 part of auxiliary cross-linking agent, 0.5 part of coupling agent and 0.4 part of anti-aging auxiliary agent.
The resin is POE;
the main cross-linking agent is tert-butyl peroxy-2-ethylhexyl carbonate.
The co-crosslinking agent triallyl isocyanurate.
The coupling agent is vinyl silane coupling agent.
The anti-aging auxiliary agent is an antioxidant.
The preparation method comprises the following steps:
(1) Uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of the embodiment 2, a main cross-linking agent, an auxiliary cross-linking agent, a coupling agent and an anti-aging auxiliary agent to obtain a mixture 1;
(2) Spraying the mixture 1 obtained in the step (1) onto POE particles, and fully stirring for 3 hours at 50 ℃ to obtain a mixture 2;
(3) And (3) carrying out tape casting on the mixture 2 by a tape casting machine at the temperature of 100 ℃ to form a film, thus obtaining the photovoltaic adhesive film.
Comparative example 1 was used
The difference from application example 1 is that: uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of the comparative example 1, a main crosslinking agent, an auxiliary crosslinking agent, a coupling agent and an anti-aging auxiliary agent to obtain a mixture 1; other steps and operations were the same as those of application example 1.
Comparative example 2 was used
The difference from application example 1 is that: uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of the comparative example 2, a main cross-linking agent, an auxiliary cross-linking agent, a coupling agent and an anti-aging auxiliary agent to obtain a mixture 1; other steps and operations were the same as those of application example 1.
Comparative example 3 was used
The difference from application example 1 is that: uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of the comparative example 3, a main crosslinking agent, an auxiliary crosslinking agent, a coupling agent and an anti-aging auxiliary agent to obtain a mixture 1; other steps and operations were the same as those of application example 1.
Effect experiment:
1. quantum efficiency:
quantum efficiency data of the pyrazoline derivative light conversion materials prepared in examples 1 to 2 and comparative examples 1 to 3 are shown in table 1 below.
TABLE 1
From the test data in table 1, it is clear that the light conversion materials obtained in examples 1-2 of the present invention have higher quantum efficiency, while the ratio of raw materials or reaction temperature in the preparation process of the light conversion materials is changed in comparative examples 1-3, and the quantum efficiency of the obtained light conversion materials is significantly reduced.
2. Component power:
The experimental method comprises the following steps: detection is according to the method in IEC 61215.
Specific detection data are shown in Table 2 below.
TABLE 2
In summary, the light conversion materials with two structures obtained in embodiments 1-2 of the present invention can absorb ultraviolet light to protect the solar cell, and emit light with a wavelength greater than 400nm for the solar cell, so that the light conversion efficiency of the solar cell can be improved to a certain extent. The quantum efficiency of the light conversion material is changed in comparative examples 1-3, and the light conversion efficiency of the solar cell is affected after the quantum efficiency is applied to the photovoltaic adhesive film.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (13)
1. A preparation method of a pyrazoline derivative light conversion material for a photovoltaic adhesive film is characterized by comprising the following steps of: the method comprises the following steps:
The first step: adding a mixed solution of anhydrous potassium carbonate and DMF into a mixture of 5-bromosalicylaldehyde and 1-bromoalkyl, reacting overnight under the protection of nitrogen, filtering after the reaction is finished, evaporating DMF, and purifying a crude product to obtain an intermediate 1; the alkyl is a C 1-12 alkyl;
And a second step of: adding a mixed solution of ethanol and sodium hydroxide into a mixture of 4-bromoacetophenone and the intermediate 1, reacting at normal temperature, filtering after the reaction is finished, washing, and recrystallizing a crude product to obtain an intermediate 2;
and a third step of: mixing the intermediate 2, 2-hydrazino benzothiazole and ethylene glycol monoethyl ether, heating and refluxing under the protection of nitrogen, filtering after the reaction is finished, and recrystallizing a crude product to obtain a pyrazoline derivative light conversion material;
the mol ratio of the 5-bromosalicylaldehyde to the 1-bromoalkyl in the first step is 1:1;
The volume ratio of the anhydrous potassium carbonate to the DMF in the first step is 1:6-10;
the reaction temperature in the first step is 70-150 ℃.
2. The method of manufacturing according to claim 1, characterized in that: the molar ratio of 4-bromoacetophenone to intermediate 1 in the second step was 1:1.
3. The method of manufacturing according to claim 1, characterized in that: in the second step, the volume ratio of the sodium hydroxide to the ethanol is 1:8-10.
4. The method of manufacturing according to claim 1, characterized in that: the concentration of sodium hydroxide in the second step was 30%.
5. The method of manufacturing according to claim 1, characterized in that: the reaction time in the second step is 1-4h.
6. The method of manufacturing according to claim 1, characterized in that: the molar ratio of the intermediate 2, the 2-hydrazino benzothiazole and the ethylene glycol monoethyl ether in the third step is 1:1:32.
7. The method of manufacturing according to claim 1, characterized in that: the reflux time in the third step is 1-4h.
8. A pyrazoline derivative light conversion material for a photovoltaic film, which is prepared by the preparation method of any one of claims 1 to 7.
9. The use of the pyrazoline derivative light conversion material for photovoltaic adhesive films, which is prepared by the preparation method of any one of claims 1 to 7, in photovoltaic devices or solar cells.
10. The utility model provides a photovoltaic glued membrane which characterized in that: comprises 0.05-0.2 part of pyrazoline derivative light conversion material prepared by the preparation method of any one of claims 1-7, 100 parts of resin, 0.4-1 part of main cross-linking agent, 0.3-1 part of auxiliary cross-linking agent, 0.1-0.5 part of coupling agent and 0.05-0.4 part of anti-aging auxiliary agent.
11. The photovoltaic film of claim 10, wherein: the resin is selected from EVA and/or POE; the main crosslinking agent is a peroxide crosslinking agent; the auxiliary crosslinking agent is an allyl crosslinking agent.
12. The photovoltaic film according to claim 10, wherein the method for preparing the photovoltaic film comprises the following steps:
(1) Uniformly mixing the pyrazoline derivative light conversion material for the photovoltaic adhesive film, which is prepared by the preparation method of any one of claims 1-10, with an auxiliary agent to obtain a mixture 1;
(2) Spraying the mixture 1 obtained in the step (1) onto resin particles, and fully stirring to obtain a mixture 2;
(3) And (3) casting the mixture 2 into a film by a casting machine to obtain the photovoltaic adhesive film.
13. The photovoltaic film according to claim 12, wherein the stirring temperature in step (2) is 30-50 ℃ and the stirring time is 2-6 hours; the temperature of the casting film in the step (3) is 60-100 ℃.
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