WO2017016177A1 - 异吡咯并吡咯二酮染料及其应用 - Google Patents
异吡咯并吡咯二酮染料及其应用 Download PDFInfo
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- WO2017016177A1 WO2017016177A1 PCT/CN2015/100048 CN2015100048W WO2017016177A1 WO 2017016177 A1 WO2017016177 A1 WO 2017016177A1 CN 2015100048 W CN2015100048 W CN 2015100048W WO 2017016177 A1 WO2017016177 A1 WO 2017016177A1
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- dye
- photoanode
- prepared
- tio
- deionized water
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- 239000000975 dye Substances 0.000 title abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000008367 deionised water Substances 0.000 claims description 27
- 229910021641 deionized water Inorganic materials 0.000 claims description 27
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 239000011521 glass Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
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- 239000000126 substance Substances 0.000 claims description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 206010070834 Sensitisation Diseases 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- -1 polytetrafluoroethylene Polymers 0.000 claims description 5
- 230000008313 sensitization Effects 0.000 claims description 5
- 230000001235 sensitizing effect Effects 0.000 claims description 5
- UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001856 Ethyl cellulose Substances 0.000 claims description 4
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 4
- 101150090068 PMII gene Proteins 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 239000004809 Teflon Substances 0.000 claims description 4
- 229920006362 Teflon® Polymers 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008151 electrolyte solution Substances 0.000 claims description 4
- 229920001249 ethyl cellulose Polymers 0.000 claims description 4
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 4
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 229940116411 terpineol Drugs 0.000 claims description 4
- 239000005416 organic matter Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000004506 ultrasonic cleaning Methods 0.000 claims description 3
- 238000002525 ultrasonication Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000003566 sealing material Substances 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract description 6
- 239000012528 membrane Substances 0.000 abstract description 5
- 238000004873 anchoring Methods 0.000 abstract description 2
- 238000003306 harvesting Methods 0.000 abstract description 2
- 238000005215 recombination Methods 0.000 abstract description 2
- 230000006798 recombination Effects 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000004065 semiconductor Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 238000011056 performance test Methods 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 229940126214 compound 3 Drugs 0.000 description 4
- 239000002159 nanocrystal Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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- 239000012074 organic phase Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 2
- IVCMUVGRRDWTDK-UHFFFAOYSA-M 1-methyl-3-propylimidazol-1-ium;iodide Chemical compound [I-].CCCN1C=C[N+](C)=C1 IVCMUVGRRDWTDK-UHFFFAOYSA-M 0.000 description 2
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 0 CCCCC(CC)CN(C(C(N(CC(CC)CCC)C1=O)=C2c3ccc[s]3)=C1c(cc1)ccc1-c(cc1)ccc1N(c1ccc(*)cc1)c1ccc(*)cc1)C2=O Chemical compound CCCCC(CC)CN(C(C(N(CC(CC)CCC)C1=O)=C2c3ccc[s]3)=C1c(cc1)ccc1-c(cc1)ccc1N(c1ccc(*)cc1)c1ccc(*)cc1)C2=O 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
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- BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2022—Light-sensitive devices characterized by he counter electrode
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/311—Purifying organic semiconductor materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
- H01G9/2013—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
-
- 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
- Y02E10/542—Dye sensitized solar cells
-
- 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
- Y02E10/549—Organic PV cells
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the invention relates to the technical field of organic dyes and dye-sensitized solar cells, in particular to isopyrrolopyrroledione dyes and applications.
- DSSCs dye-sensitized solar cells
- Sensitizing dyes are an important part of the battery, which directly affects the performance and practical application of the battery, and can be divided into two categories: pure organic dyes and metal complex dyes.
- metal complex dyes have the advantage of high photoelectric conversion efficiency
- pure organic dyes also have the advantages of large structural adjustability, easy synthesis and separation, and relatively low cost.
- DPP pyrrolopyrroledione
- isoDPP isopyrrolopyrroledione
- the invention designs and synthesizes a pure organic dye which uses 4,4'-dihexyloxytriphenylamine as an electron donor, isopyrrolopyrroledione as a ⁇ bridge, and cyanoacetic acid as an electron acceptor and anchoring group.
- the dye has the advantages of simple structure, easy synthesis, good photoelectric conversion performance and the like.
- the invention discloses a dye based on isopyrrolopyrroledione as a ⁇ bridge and its application in dye-sensitized solar cells.
- the invention synthesizes a novel class of metal-free pure organic photosensitive dyes, such dyes are 4,4'-dihexyloxytriphenylamine as electron donor, isopyrrolopyrroledione is ⁇ bridge, and cyanoacetic acid is A pure organic dye of an electron acceptor and an anchor group, and an alkyl chain is introduced on the isopyrrolopyrroledione group.
- These dyes have good application properties on dye-sensitized solar cells. Its structural formula is as follows:
- R 1 and R 2 are a C 1 -C 20 linear alkyl group, a C 1 -C 20 branched alkyl group or a C 1 -C 20 alkoxy group, and R 1 and R 2 may be the same or different;
- a 1 and A 2 are thiophene, benzene ring, furan, 3,4-dioxyethylenethiophene or pyrrole, and A 1 and A 2 may be the same or different.
- the method for synthesizing a dye based on isopyrrolopyrroledione as a ⁇ bridge is simple, and the raw material is cheap and easy to obtain, for example
- the synthesis steps are as follows:
- the use of the isopyrrolopyrroledione dye synthesized by the invention in dye-sensitized solar cells including dye-sensitized sun Battery composition and construction, preparation steps and battery performance test:
- Composition and structure of dye-sensitized solar cells divided into conductive glass substrates (usually fluorine-doped SnO 2 transparent conductive glass, ie FTO), photoanodes, sensitizers, electrolytes and counter electrodes (generally platinized) Conductive glass) five components; wherein the photo-anode substrate working area is provided with a nanoporous TiO 2 film in the middle of the conductive glass, which can be used to adsorb the dye; the counter electrode is also called the photocathode, and a catalyst is arranged in the middle of the conductive glass on the working area of the substrate.
- conductive glass substrates usually fluorine-doped SnO 2 transparent conductive glass, ie FTO
- photoanodes sensitizers
- electrolytes electrolytes
- counter electrodes generally platinized Conductive glass
- the catalyst is mostly Pt; the photoanode and the photocathode are relatively spaced apart, and the periphery of the nanoporous TiO 2 film is sealed with a sealing material to form a closed cavity filled with an electrolyte and a sensitizer (ie, isopyrrolopyrrole II) Ketone dye).
- a sensitizer ie, isopyrrolopyrrole II
- FTO conductive glass
- the nanocrystalline TiO 2 prepared particles were added to ethanol, acetic acid, terpineol, ethyl cellulose, the The mixture is sufficiently ground to obtain a slurry-like substance, and the desired white viscous TiO 2 nanocrystalline slurry is obtained by ultrasonication;
- the conductive surface of the treated conductive glass is faced upward, the screen plate is placed above the glass, the mesh distance of 0.5 to 3 cm is controlled, and the prepared TiO 2 nanocrystalline slurry is placed on the screen for printing.
- the thickness of the TiO 2 film is controlled as needed, and is about 8 to 20 ⁇ m (area of 2 to 4 ⁇ 2 to 4 mm).
- the prepared photoanode is placed in an oven and dried at 100 to 150 ° C, and then placed in a muffle. The furnace is sequentially treated at different temperatures (baked at 300-350 ° C for 3-10 min, baked at 300-400 ° C for 3-10 min, baked at 400-500 ° C for 10-20 min, baked at 450-550 ° C for 10-20 min) to fully remove.
- the organic substance on the membrane is then immersed in the prepared 0.1-0.3M TiCl 4 aqueous solution for 30 min to 1.5 h, and the treatment is finished with deionized water and ethanol, and placed in a muffle furnace to raise the temperature to 450-550 ° C again. Bake for 25 to 40 minutes, cool to 60 to 80 ° C and set aside;
- preparation steps of the dye-sensitized solar cell include the following specific steps:
- FTO conductive glass
- the treated conductive glass was placed with the conductive surface facing up, the screen plate was placed above the glass, the mesh distance of 1 cm was controlled, and the prepared TiO 2 nanocrystal slurry was placed on the screen for printing.
- the thickness of the TiO 2 film is controlled as needed, and is about 17 ⁇ m (area of 4 ⁇ 4 mm) used in this chapter.
- the prepared photoanodes were placed in an oven and dried at 125 °C. It was placed in a muffle furnace and then treated at different temperatures (bake at 325 ° C for 5 min, 375 ° C for 5 min, 450 ° C for 15 min, and 500 ° C for 15 min) to remove the organic matter on the membrane.
- Battery performance test The lead wire is taken out from the photoanode and the photocathode of the battery respectively, and connected to the battery performance test device.
- the working area of the battery is 0.16 cm 2 , and the sunlight is simulated by a solar simulator to adjust the light intensity to 100 mW.
- the /cm 2 test is based on the JV curve of the dye-sensitized battery.
- the present invention has the following advantages and technical effects:
- isopyrrolopyrroledione groups in the ⁇ bridge can expand the spectral response, effectively inhibit dye aggregation and electron recombination, prolong the electron lifetime, and improve the photoelectric conversion efficiency of the sensitized solar cell.
- Example 1 The dye obtained in Example 1 was subjected to ultraviolet-visible absorption spectroscopy, and its ultraviolet-visible absorption spectrum is shown in Fig. 1.
- the dye-sensitized solar cell of the present invention is produced as follows:
- the treated conductive glass was placed with the conductive surface facing up, the screen plate was placed above the glass, the mesh distance of 1 cm was controlled, and the prepared TiO 2 nanocrystal slurry was placed on the screen for printing.
- the thickness of the TiO 2 film is controlled as needed, and is about 17 ⁇ m (area of 4 ⁇ 4 mm) used in this chapter.
- the prepared photoanodes were placed in an oven and dried at 125 °C. It was placed in a muffle furnace and then treated at different temperatures (bake at 325 ° C for 5 min, 375 ° C for 5 min, 450 ° C for 15 min, and 500 ° C for 15 min) to remove the organic matter on the membrane.
- the tape is made into a suitable inner hole plastic by a puncher, and the insulating film is placed on the sensitized photoanode so that the photoanode is just in the inner hole of the insulating film.
- 1 to 2 drops of the electrolyte prepared in (4) were added dropwise, and the platinum counter electrode prepared by capping on the photoanode was fixed with clips on both sides to form an open sensitizing dye solar cell to be tested.
- Battery performance test The lead wire is taken out from the photoanode and the photocathode of the battery, and connected to the battery performance test device.
- the working area of the battery is 0.16 cm 2 , and the sunlight is simulated by a solar simulator to adjust the light intensity to 100 mW.
- the /cm 2 test is based on the JV curve of the dye-sensitized battery.
- the dyes synthesized in the first embodiment were assembled into batteries, and the wires were taken out from the photoanode and the photocathode respectively, and connected to the battery performance test device.
- the solar simulator simulates sunlight, and the light intensity is adjusted to 100 mW/cm 2 to test the JV curve of the battery based on the dye sensitization, respectively.
- the dye isoDPP exhibits high photoelectric conversion efficiency with good short-circuit current and open circuit voltage. This is mainly due to the dye's ability to capture light and to inhibit aggregation.
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Abstract
Description
Claims (3)
- 权利要求1所述在π桥中引入异吡咯并吡咯二酮基团的纯有机染料在染料敏化太阳电池中的应用,其特征在于:所述染料敏化太阳电池主要由导电玻璃基质、光阳极、敏化剂、电解质和对电极组成;其中光阳极基板工作区域一侧导电玻璃中间设有纳米多孔TiO2薄膜,可用以吸附染料;对电极也称光阴极,其基板工作区域一侧导电玻璃中间设有催化剂层,其中催化剂为Pt;光阳极和光阴极相对间隔设置,所述纳米多孔TiO2薄膜周边用密封材料密封形成密闭的腔体,腔体内填充有电解质和敏化剂即异吡咯并吡咯二酮染料。
- 根据权利要求2所述的在π桥中引入异吡咯并吡咯二酮染料在染料敏化太阳电池中的应用,其特征在于,制备步骤如下:(1)导电玻璃(FTO)的预处理:将裁好的FTO超声清洗,并用去离子水冲洗3~6次,再置于KOH的饱和乙醇溶液中浸泡16~36h,再依次用去离子水、丙酮、去离子水和乙醇超声清洗,干燥后保存待用;(2)光阳极的制备:室温下,将10~25mLTi(OBu)2和15~30mLEtOH的混合液剧烈搅拌下加入35~80mL乙酸和去离子水并继续搅拌30min~2h,将此混合液移入内衬特氟隆(聚四氟乙烯)的高压釜中,于200~280℃处理8~20h后自然冷却至室温,将所得的悬浊液过滤,依次用去离子水和乙醇洗涤3~6次,于烘箱中40~60℃下烘4~8h至干后得到TiO2纳晶颗粒,向制备好的TiO2纳晶颗粒中分别加入乙醇、乙酸、松油醇、乙基纤维素后,将该混合物充分研磨得到泥浆状物质,经超声得到所需的白色粘性TiO2纳晶浆料;将处理好的导电玻璃导电面朝上,将丝网板置于玻璃上方,控制0.5~3cm的网距,将制备好的TiO2纳晶浆料置于丝网上进行印刷;将制备好的光阳极放入烘箱中于100~150℃干燥,再放于马弗炉中依次在不同的温度下处理:300~350℃烘焙3~10min,300~400℃烘焙3~10min,400~500℃烘焙10~20min,450~550℃烘焙10~20min,以充分除去膜上的有机物质,然后浸于制备的0.1~0.3M的TiCl4水溶液中处理30min~1.5h,处理结束用去离子水和乙醇冲洗干净,置于马弗炉中升温到450~550℃再次烘焙25~40min,冷却至60~80℃后备用;(3)染料溶液的配制:将所述的异吡咯并吡咯二酮染料溶于氯仿/甲醇的混合溶剂中, 配制成1×10-4~3×10-4mol·L-1染料溶液,氯仿/甲醇的体积比为4/1~1/4;(4)电解质溶液的配制:0.5M~0.71-甲基-3-丙基碘化咪唑鎓(PMII),0.03~0.07M硫氰酸胍,0.03~0.07M LiI,0.01~0.04M I2和0.15~0.40M叔丁基吡啶(TBP)溶于乙腈,并混合均匀得到澄清的溶液;(5)光阳极的敏化:将步骤(2)制备的光阳极浸泡于步骤(3)配制的染料溶液中,在阴暗避光环境中染浴10~20小时后,取出并用氯仿/甲醇的混合溶剂冲洗除去表面的残留或膜表面的染料,吹干后保存干燥避光环境以待封装,备用;氯仿/甲醇的体积比为4/1~1/4;(6)用打孔器将胶带制成合适的内孔塑料,将此绝缘薄膜置于已敏化的光阳极,使光阳极恰好处于绝缘薄膜内孔里,向TiO2膜表面滴加1~2滴步骤(5)制备的电解液,并在光阳极上盖制备的铂对电极,两边用夹子固定即形成待测的开放性敏化染料太阳电池。
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