WO2015125587A1 - 光電変換素子及び太陽電池 - Google Patents
光電変換素子及び太陽電池 Download PDFInfo
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- WO2015125587A1 WO2015125587A1 PCT/JP2015/052684 JP2015052684W WO2015125587A1 WO 2015125587 A1 WO2015125587 A1 WO 2015125587A1 JP 2015052684 W JP2015052684 W JP 2015052684W WO 2015125587 A1 WO2015125587 A1 WO 2015125587A1
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- WO
- WIPO (PCT)
- Prior art keywords
- photoelectric conversion
- conversion element
- transport layer
- hole transport
- electrode
- Prior art date
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- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- GGYFMLJDMAMTAB-UHFFFAOYSA-N selanylidenelead Chemical compound [Pb]=[Se] GGYFMLJDMAMTAB-UHFFFAOYSA-N 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- ZRXVCYGHAUGABY-UHFFFAOYSA-O tris(4-bromophenyl)azanium Chemical compound C1=CC(Br)=CC=C1[NH+](C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 ZRXVCYGHAUGABY-UHFFFAOYSA-O 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- 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
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
- H01G9/2018—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte characterised by the ionic charge transport species, e.g. redox shuttles
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
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- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
- H01G9/209—Light trapping arrangements
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
- H10K30/151—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2 the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2
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- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
- H10K30/152—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2 the wide bandgap semiconductor comprising zinc oxide, e.g. ZnO
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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
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- 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
Definitions
- the present invention relates to a photoelectric conversion element and a method for manufacturing a solar cell.
- Patent Document 1 Non-Patent Documents 1 and 2.
- the solar cell has a structure in which a porous metal oxide semiconductor is provided on a transparent conductive glass substrate, a dye adsorbed on the surface thereof, an electrolyte having a redox pair, and a counter electrode.
- a metal oxide semiconductor electrode such as titanium oxide is made porous to increase the surface area, and a ruthenium complex is a single molecule as a dye. The photoelectric conversion efficiency is remarkably improved by the adsorption.
- the printing method can be applied to the method for manufacturing the photoelectric conversion element, it is expected that the manufacturing cost can be reduced because expensive manufacturing equipment is not required.
- the solar cell contains iodine and a volatile solvent, and there are problems such as reduction in power generation efficiency due to deterioration of the iodine redox system, volatilization and leakage of the electrolyte.
- Non-Patent Document 3 copper iodide is used as a constituent material of the p-type semiconductor layer. Although it has a relatively good photoelectric conversion efficiency immediately after the production, it is known that it will be halved in a few hours due to deterioration due to an increase in copper iodide crystal grains and the like. Therefore, in the solar cell described in Non-Patent Document 4, crystallization of copper iodide is suppressed by adding imidazolinium thiocyanate, but this is not sufficient.
- Non-Patent Document 5 A solid-type dye-sensitized solar cell using the organic hole transport material described in Non-Patent Document 5 has been reported by Hagen et al. And improved by Graetzel et al. (See Non-Patent Document 6).
- the charge transport layer is formed by vacuum deposition of the triphenylamine compound. Therefore, the triphenylamine compound cannot reach the internal pores of the porous semiconductor, and only low conversion efficiency is obtained.
- Non-Patent Document 6 a spiro-type hole transport material is dissolved in an organic solvent, and a composite of nanotitania particles and a hole transport material is obtained using spin coating.
- the optimum value of the nanotitania particle thickness in this solar cell is about 2 ⁇ m, which is very thin compared to 10 ⁇ m to 20 ⁇ m when using an iodine electrolyte. Therefore, the amount of the dye adsorbed on the titanium oxide is small, and it is difficult to perform sufficient light absorption and carrier generation, and the characteristics when using the electrolytic solution are not achieved.
- Non-Patent Document 7 As a solid-state solar cell of the type using the conductive polymer, Osaka University Yanagida et al. Have reported that using polypyrrole (see Non-Patent Document 7). Even in the solid-state solar cell, only low conversion efficiency is obtained.
- the solid dye-sensitized solar cell using the polythiophene derivative described in Patent Document 3 is provided with a charge transfer layer on the porous titanium oxide electrode adsorbing the dye using an electrolytic polymerization method. May be desorbed from titanium oxide, or the pigment may be decomposed. Furthermore, the polythiophene derivative is very problematic in durability.
- Non-Patent Document 8 a conventional electrolyte type dye-sensitized solar cell using iodine or the like has photoelectric conversion characteristics in room light that is weaker than that of an amorphous silicon solar cell.
- the electrolyte-type dye-sensitized solar cell contains iodine and a volatile solvent as described above, and has problems such as reduction in power generation efficiency due to deterioration of the iodine redox system, volatilization and leakage of the electrolyte.
- Non-Patent Document 9 When the internal resistance is increased, the short circuit current density is deteriorated and the photoelectric conversion characteristics are deteriorated. Further, when the internal resistance is lowered, the open circuit voltage is deteriorated and the photoelectric conversion characteristics are deteriorated. That is, it is very difficult to increase both the internal resistance and the good photoelectric conversion characteristics.
- the open voltage obtained by the photoelectric conversion element is lower in weak light such as the room light than in the case of simulated sunlight. For this reason, in order to obtain an output voltage necessary for driving an electronic circuit, it is necessary to obtain a high open circuit voltage.
- Non-Patent Document 10 A basic substance capable of obtaining a high open-circuit voltage has been conventionally reported (see Non-Patent Document 10). However, in an electrolyte-type dye-sensitized solar cell such as iodine, there is no basic material that can obtain a photoelectric conversion property superior to that of 4-tertiarybutylpyridine which has been conventionally used.
- An object of the present invention is to solve the above-mentioned problems and provide a solid-state photoelectric conversion element having superior photoelectric conversion properties as compared with the conventional one.
- the subject is a photoelectric conversion element having a first electrode, a hole blocking layer, an electron transport layer, a first hole transport layer, and a second electrode, Said 1st hole transport layer is solved by the photoelectric conversion element containing at least 1 among the basic compounds represented by the following general formula (1a) and general formula (1b).
- R 1 and R 2 represent a substituted or unsubstituted alkyl group or an aromatic hydrocarbon group, which may be the same or different, and R 1 and R 2 are And may be bonded to form a substituted or unsubstituted heterocyclic group containing a nitrogen atom.
- FIG. 1 is a schematic diagram illustrating an example of a cross section perpendicular to the stacking direction of the structure of the photoelectric conversion element according to the present invention.
- FIG. 1 is an example of a schematic diagram illustrating a cross section orthogonal to the stacking direction of the photoelectric conversion element and the solar cell.
- the first electrode 2 is provided on the substrate 1
- the photosensitizing material 5 is adsorbed on the hole blocking layer 3
- the electron transport layer 4 and the electron transport layer made of titanium oxide
- the hole transport layer 6 is sandwiched between the second electrode 7.
- the first electrode 2 is not particularly limited as long as it is a conductive substance that is transparent to visible light, and a known one used for a normal photoelectric conversion element, a liquid crystal panel, or the like can be used.
- Examples of the material of the first electrode 2 include indium tin oxide (hereinafter referred to as ITO), fluorine-doped tin oxide (hereinafter referred to as FTO), antimony-doped tin oxide (hereinafter referred to as ATO), and indium.
- ITO indium tin oxide
- FTO fluorine-doped tin oxide
- ATO antimony-doped tin oxide
- -Zinc oxide, niobium / titanium oxide, graphene, etc. are mentioned. These may be used alone or in a plurality of layers.
- the thickness of the first electrode 2 is preferably 5 nm to 100 ⁇ m, more preferably 50 nm to 10 ⁇ m.
- the first electrode 2 is preferably provided on the substrate 1 made of a material transparent to visible light in order to maintain a certain hardness.
- the substrate 1 for example, glass, a transparent plastic plate, a transparent plastic film, an inorganic transparent crystal, or the like is used.
- FTO-coated glass ITO-coated glass
- zinc oxide aluminum-coated glass
- FTO-coated transparent plastic film ITO-coated transparent
- a plastic film etc. are mentioned.
- metal lead wire examples include metals such as aluminum, copper, silver, gold, platinum, and nickel.
- the metal lead wire can be formed by a method of installing the ITO or the FTO on the substrate 1 by vapor deposition, sputtering, pressure bonding, or the like.
- the hole blocking layer 3 is not particularly limited as long as it is transparent to visible light and has an electron transporting material, but titanium oxide is particularly preferable.
- titanium oxide is particularly preferable.
- the titanium oxide film is formed by a sol-gel method or a hydrolyzing method from titanium tetrachloride to form a wet film, but the resistance is low.
- a sputtering method for forming a dry film is more preferable.
- the hole blocking layer 3 is also formed for the purpose of preventing electronic contact between the first electrode 2 and the hole transport layer 6.
- the thickness of the hole blocking layer 3 is not particularly limited, but is preferably 5 nm to 1 ⁇ m, more preferably 500 nm to 700 nm for wet film formation, and more preferably 10 nm to 30 nm for dry film formation.
- the photoelectric conversion element and the solar cell of the present invention form the porous electron transport layer 4 on the hole blocking layer 3, and may be a single layer or a multilayer.
- the multi-layer it is possible to apply multi-layer coatings of semiconductor fine particle dispersions having different particle diameters, or to apply multi-layer coatings of different types of semiconductors, resins, and additives. When the thickness is insufficient with a single application, the multilayer application is an effective means.
- the thickness of the electron transport layer 4 is preferably 100 nm to 100 ⁇ m.
- the semiconductor is not particularly limited, and a known semiconductor can be used. Specifically, a single semiconductor such as silicon or germanium, a compound semiconductor typified by a metal chalcogenide, a compound having a perovskite structure, or the like can be given.
- the metal chalcogenides include titanium, tin, zinc, iron, tungsten, zirconium, hafnium, strontium, indium, cerium, yttrium, lanthanum, vanadium, niobium, or tantalum oxide, cadmium, zinc, lead, Silver, antimony, bismuth sulfide, cadmium, lead selenide, cadmium telluride and the like.
- Examples of other compound semiconductors include phosphides such as zinc, gallium, indium, cadmium, gallium arsenide, copper-indium-selenide, copper-indium-sulfide, and the like.
- Examples of the compound having a perovskite structure include strontium titanate, calcium titanate, sodium titanate, barium titanate, and potassium niobate. These may be used alone or in combination of two or more.
- an oxide semiconductor is preferable, and titanium oxide, zinc oxide, tin oxide, and niobium oxide are particularly preferable.
- the crystal type of these semiconductors is not particularly limited, and may be single crystal, polycrystal, or amorphous.
- the size of the semiconductor fine particles is not particularly limited, but the average primary particle size is preferably 1 nm to 100 nm, more preferably 5 nm to 50 nm.
- the efficiency can be improved by mixing or laminating semiconductor particles having a larger average particle diameter to scatter incident light.
- the average particle diameter of the semiconductor particles is preferably 50 nm to 500 nm.
- the method for producing the electron transport layer 4 is not particularly limited, and examples thereof include a method of forming a thin film in a vacuum such as sputtering and a wet film forming method.
- the wet film forming method is preferable, and a method in which a paste in which the semiconductor fine particle powder or sol is dispersed is prepared and applied to the electron collecting electrode substrate is more preferable.
- the coating method is not particularly limited and can be performed according to a known method, for example, a dip method, a spray method, a wire bar method, a spin coating method, a roller coating method, Examples thereof include a blade coating method and a gravure coating method.
- various methods such as a letterpress, an offset, a gravure, an intaglio, a rubber plate, screen printing, can be used, for example.
- the semiconductor fine particle dispersion is prepared by mechanical pulverization or using a mill, it is formed by dispersing at least semiconductor fine particles alone or a mixture of semiconductor fine particles and a resin in water or an organic solvent.
- the resin examples include polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, acrylic acid ester, and methacrylic acid ester, silicon resin, phenoxy resin, polysulfone resin, polyvinyl butyral resin, polyvinyl formal resin, and polyester resin. , Cellulose ester resin, cellulose ether resin, urethane resin, phenol resin, epoxy resin, polycarbonate resin, polyarylate resin, polyamide resin, polyimide resin and the like.
- vinyl compounds such as styrene, vinyl acetate, acrylic acid ester, and methacrylic acid ester
- silicon resin phenoxy resin
- polysulfone resin polyvinyl butyral resin
- polyvinyl formal resin and polyester resin.
- Cellulose ester resin Cellulose ester resin, cellulose ether resin, urethane resin, phenol resin, epoxy resin, polycarbonate resin, polyarylate resin, polyamide resin, polyimide resin and the like.
- Examples of the solvent for dispersing the semiconductor fine particles include alcohol solvents such as water, methanol, ethanol, isopropyl alcohol, and ⁇ -terpineol, ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, ethyl formate, ethyl acetate, Or ester solvents such as n-butyl acetate, ether solvents such as diethyl ether, dimethoxyethane, tetrahydrofuran, dioxolane, or dioxane, N, N-dimethylformamide, N, N-dimethylacetamide, or N-methyl-2- Amide solvents such as pyrrolidone, dichloromethane, chloroform, bromoform, methyl iodide, dichloroethane, trichloroethane, trichloroethylene, chlorobenzene, o-dichloro
- the semiconductor fine particle paste obtained by the dispersion of the semiconductor fine particles or the sol-gel method may be an acid such as hydrochloric acid, nitric acid or acetic acid, polyoxyethylene (10) octylphenyl ether.
- a surfactant such as acetylacetone, a chelating agent such as 2-aminoethanol, and ethylenediamine can be added.
- thickener for the purpose of improving the film forming property.
- the thickener include polymers such as polyethylene glycol and polyvinyl alcohol, and thickeners such as ethyl cellulose.
- the semiconductor fine particles may be subjected to firing, microwave irradiation, electron beam irradiation, or laser beam irradiation in order to bring the particles into electronic contact with each other after coating and to improve film strength and adhesion to the substrate. preferable. These processes may be performed alone or in combination of two or more.
- the range of the firing temperature is not particularly limited, but if the temperature is raised excessively, the resistance of the substrate may be increased or the substrate may be melted, and therefore 30 ° C. to 700 ° C. is preferable, and 100 ° C. to 600 ° C. ° C is more preferred.
- the firing time is not particularly limited, but is preferably 10 minutes to 10 hours.
- the microwave irradiation may be performed from the electron transport layer 4 formation side or from the back side. Although there is no restriction
- Electrochemical plating using a titanium trichloride aqueous solution may be performed.
- a film in which the semiconductor fine particles having a diameter of several tens of nanometers are laminated by sintering or the like forms a porous state.
- This nanoporous structure has a very high surface area, which can be expressed using a roughness factor.
- the roughness factor is a numerical value representing the actual area inside the porous with respect to the area of the semiconductor fine particles applied to the substrate. Therefore, the roughness factor is preferably as large as possible, but it is also related to the film thickness of the electron transport layer 4 and is preferably 20 or more in the present invention.
- the photosensitizing material is adsorbed on the surface of the electron transporting semiconductor that is the electron transporting layer 4.
- the photosensitizing material those represented by the general formula (2) are preferable.
- R 3 represents a substituted or unsubstituted alkyl group.
- Dye1 R 3 CH 2 CH 3 (Japanese scientific material dictionary number: J2.477.478C, J3.081.465G)
- Dye2 R 3 (CH 2 ) 3 CH 3
- Dye3 R 3 C (CH 3 ) 3
- Dye4 R 3 (CH 2 ) 9 CH 3
- Dye5 R 3 (CH 2 ) 2 COOH
- Dye6 R 3 (CH 2 ) 4 COOH
- Dye7 (CH 2 ) 7 COOH
- Dye8 R 3 (CH 2 ) 10 COOH (Japanese scientific substance dictionary number: J3.113.583D)
- the compound represented by the general formula (2) can be synthesized by the method described in Dye and Pigments 91 (2011) 145-152.
- the photosensitizing material 5 is not limited to the above as long as it is a compound that is photoexcited by the excitation light used, and specific examples thereof include the following compounds.
- JP-A-11-86916 JP-A-11-214730, JP-A-2000-106224, JP-A-2001-76773, JP-A-2003-7359. Described in JP-A-11-214731, JP-A-11-238905, JP-A-2001-52766, JP-A-2001-76775, JP-A-2003-7360, etc.
- Merocyanine dyes 9-arylxanthene compounds described in JP-A-10-92477, JP-A-11-273754, JP-A-11-273755, JP-A-2003-3173, etc., JP-A-10-93118 Triarylmethane compounds described in Japanese Patent Laid-Open No.
- the metal complex compound, the coumarin compound, the polyene compound, the indoline compound, and the thiophene compound are preferable.
- a method for adsorbing the photosensitizing material 5 to the electron transporting layer 4 a method of immersing an electron current collecting electrode containing semiconductor fine particles in a photosensitizing material solution or dispersion, a solution or dispersion is used as an electron transporting layer. It is possible to use a method of applying to and adsorbing to the surface.
- a method for immersing the electron current collecting electrode containing semiconductor fine particles in the photosensitizing material solution or dispersion for example, a dipping method, a dipping method, a roller method, an air knife method or the like can be used.
- a method for applying the solution or dispersion liquid to the electron transport layer and adsorbing it for example, a wire bar method, a slide hopper method, an extrusion method, a curtain method, a spin method, a spray method, or the like can be used. Further, it may be adsorbed in a supercritical fluid using carbon dioxide or the like.
- a condensing agent When adsorbing the photosensitizing material 5, a condensing agent may be used in combination.
- the condensing agent has a catalytic action that seems to physically or chemically bond the photosensitizing material and the electron transport compound to the inorganic surface, or acts stoichiometrically to move the chemical equilibrium advantageously. Any of those to be made may be used. Furthermore, you may add a thiol and a hydroxy compound as said condensation adjuvant.
- Examples of the solvent for dissolving or dispersing the photosensitizing material 5 include, for example, alcohol solvents such as water, methanol, ethanol, and isopropyl alcohol, ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, ethyl formate, Ester solvents such as ethyl acetate or n-butyl acetate, ether solvents such as diethyl ether, dimethoxyethane, tetrahydrofuran, dioxolane, or dioxane, N, N-dimethylformamide, N, N-dimethylacetamide, or N-methyl Amide solvents such as -2-pyrrolidone, dichloromethane, chloroform, bromoform, methyl iodide, dichloroethane, trichloroethane, trichloroethylene, chlorobenzene, o-dich
- an aggregating and dissociating agent may be used in combination.
- the aggregating / dissociating agent is preferably a steroid compound such as cholic acid or chenodeoxycholic acid, a long-chain alkyl carboxylic acid or a long-chain alkyl phosphonic acid, and is appropriately selected according to the dye used.
- the addition amount of the aggregating and dissociating agent is preferably 0.01 to 500 parts by mass, more preferably 0.1 to 100 parts by mass with respect to 1 part by mass of the dye.
- the temperature at which the photosensitizing material is adsorbed alone or the temperature at which the photosensitizing material and the aggregating / dissociating agent are adsorbed is preferably ⁇ 50 ° C. or more and 200 ° C. or less. Moreover, this adsorption may be carried out while standing or stirring.
- the stirring method is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include a stirrer, a ball mill, a paint conditioner, a sand mill, an attritor, a disperser, and ultrasonic dispersion.
- the time required for the adsorption is preferably 5 seconds or more and 1000 hours or less, more preferably 10 seconds or more and 500 hours or less, and further preferably 1 minute or more and 150 hours.
- the adsorption is preferably performed in a dark place.
- the hole transport material 6 is not particularly limited as long as it contains at least one of an organic hole transport material and a basic compound represented by the general formula (1a) or the general formula (1b). It can be appropriately selected depending on the case.
- a general hole transport layer an electrolyte solution in which a redox couple is dissolved in an organic solvent, a gel electrolyte in which a liquid in which a redox couple is dissolved in an organic solvent is impregnated in a polymer matrix, and a molten salt containing the redox couple Solid electrolytes, inorganic hole transport materials, organic hole transport materials, and the like are used.
- Organic hole transport material can be used for either a single layered hole transporting layer 6 made of a single material or a stacked hole transporting layer 6 made of a plurality of compounds.
- the organic hole transport material used in the single layer structure made of the single material a known organic hole transport compound is used. Specific examples thereof include oxadiazole compounds disclosed in JP-B No. 34-5466, triphenylmethane compounds disclosed in JP-B No. 45-555, JP-B No. 52-4188, and the like. Pyrazoline compounds shown, hydrazone compounds shown in JP-B-55-42380, etc., oxadiazole compounds shown in JP-A-56-123544, etc., JP-A-54-58445 Tetraarylbenzidine compounds shown in JP-A-58-65440 or JP-A-60-98437, Adv. Mater. , 813, vol. 17, spirobifluorene compounds such as spiro-OMeTAD described in (2005).
- the hole transport material called spiro-OMeTAD is preferable in that it exhibits excellent photoelectric conversion characteristics.
- a known hole transport polymer material is used as the polymer material used for the hole transport layer 6 close to the second electrode 7 used in the laminated structure.
- a known hole transport polymer material includes poly (3-n-hexylthiophene), poly (3-n-octyloxythiophene), poly (9,9′-dioctyl-fluorene-co-bithiophene), poly (3,3 ′′ '-Didodecyl-quarterthiophene), poly (3,6-dioctylthieno [3,2-b] thiophene), poly (2,5-bis (3-decylthiophen-2-yl) thieno [3,2-b Thiophene), poly (3,4-didecylthiophene-co-thieno [3,2-b] thiophene), poly (3,6-dioctylthieno [3,2-b] thiophene-co-thieno [3, 2-b]
- additives may be added to the organic hole transport material.
- the additive include iodine, lithium iodide, sodium iodide, potassium iodide, cesium iodide, calcium iodide, copper iodide, iron iodide, silver iodide and other metal iodides, Quaternary ammonium salts such as tetraalkylammonium iodide, pyridinium iodide, metal bromides such as lithium bromide, sodium bromide, potassium bromide, cesium bromide, calcium bromide, Bromine salts of quaternary ammonium compounds such as tetraalkylammonium bromide and pyridinium bromide, Metal chlorides such as copper chloride and silver chloride, metal acetates such as copper acetate, silver acetate and palladium acetate, Metal sulfates such as copper sulfate and zinc sulf
- a particularly high open-circuit voltage can be obtained by adding a basic compound represented by the following general formula (1a) or general formula (1b) to the organic hole transport material. Further, the internal resistance of the photoelectric conversion element is increased, and the loss current in weak light such as room light can be reduced. Therefore, an open circuit voltage higher than that of a conventional basic compound can be obtained.
- R 1, R 2 represents a substituted or unsubstituted alkyl group or an aromatic hydrocarbon group, may be the same or different. Also, R 1, R 2 are each And may form a substituted or unsubstituted heterocyclic group containing a nitrogen atom, and examples of the substituent include an alkyl group, an aromatic hydrocarbon group, and a substituted or unsubstituted alkoxy group.
- the hole transport layer 6 uses the organic hole transport material and is different from the hole transport model using the iodine electrolyte solution or the like. Therefore, the amount of decrease in the short-circuit current density is small, and a high open circuit voltage can be obtained, whereby excellent photoelectric conversion characteristics can be obtained. Furthermore, when photoelectric conversion was performed in weak light such as room light, which is rarely reported, it was verified that a particularly significant advantage appears.
- the addition amount of the basic compound represented by the general formula (1a) or the general formula (1b) in the hole transport layer 6 is 1 part by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the organic hole transport material. It is preferable that it is 5 mass parts or more and 15 mass parts or less.
- R 1 and R 2 represent a substituted or unsubstituted alkyl group or an aromatic hydrocarbon group, and may be the same or different. In addition, R 1 and R 2 may be mutually different. And a substituted or unsubstituted heterocyclic group containing a nitrogen atom may be formed, and X represents a halogen element.
- the oxidizing agent for making a part of said organic hole transport material into a radical cation for the purpose of improving electroconductivity.
- the oxidizing agent include tris (4-bromophenyl) aminium hexachloroantimonate, silver hexafluoroantimonate, nitrosonium tetrafluorate, silver nitrate, and cobalt complex compounds.
- the added oxidizing agent may or may not be taken out of the system after the addition.
- the hole transport layer 6 is formed directly on the electron transport layer 4 carrying the photosensitizing material.
- the method of forming a thin film in vacuum, such as vacuum deposition, and the wet film forming method are mentioned. In consideration of production cost and the like, the wet film forming method is particularly preferable, and a method of coating on the electron transport layer 4 is preferable.
- the application method is not particularly limited and can be performed according to a known method, for example, a dip method, a spray method, a wire bar method, a spin coating method, a roller coating method, Examples thereof include a blade coating method and a gravure coating method.
- a wet printing method various methods, such as a letterpress, an offset, a gravure, an intaglio, a rubber plate, screen printing, can be used, for example.
- the film may be formed in a supercritical fluid or a subcritical fluid having a temperature and pressure lower than the critical point.
- the supercritical fluid exists as a non-aggregating high-density fluid in a temperature / pressure region that exceeds the limit (critical point) at which gas and liquid can coexist, and does not aggregate even when compressed.
- the fluid is not particularly limited as long as it is in the above state, and can be appropriately selected according to the purpose. However, a fluid having a low critical temperature is preferable.
- the supercritical fluid examples include carbon monoxide, carbon dioxide, ammonia, nitrogen, water, ercol solvents such as methanol, ethanol, n-butanol, ethane, propane, 2,3-dimethylbutane, benzene, toluene, and the like.
- ercol solvents such as methanol, ethanol, n-butanol, ethane, propane, 2,3-dimethylbutane, benzene, toluene, and the like.
- hydrocarbon solvents halogen solvents such as methylene chloride and chlorotrifluoromethane
- ether solvents such as dimethyl ether.
- the carbon dioxide since the carbon dioxide has a critical pressure of 7.3 MPa and a critical temperature of 31 ° C., it is particularly preferable because it can easily create a supercritical state and is nonflammable and easy to handle.
- these fluids may be one kind alone or a mixture of two or more kinds.
- the subcritical fluid is not particularly limited as long as it exists as a high pressure liquid in a temperature and pressure region near the critical point, and can be appropriately selected according to the purpose.
- the compounds mentioned as the supercritical fluid can also be suitably used as the subcritical fluid.
- the critical temperature and critical pressure of the supercritical fluid are not particularly limited and may be appropriately selected depending on the intended purpose.
- the critical temperature is preferably ⁇ 273 ° C. or higher and 300 ° C. or lower, preferably 0 ° C. or higher and 200 ° C. or lower. Is particularly preferred.
- an organic solvent or an entrainer can be used in combination. By adding the organic solvent and the entrainer, the solubility in the supercritical fluid can be easily adjusted.
- the organic solvent is not particularly limited and may be appropriately selected depending on the intended purpose.
- examples thereof include ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and esters such as ethyl formate, ethyl acetate, and n-butyl acetate.
- Solvents such as diisopropyl ether, dimethoxyethane, tetrahydrofuran, dioxolane, dioxane, amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dichloromethane, chloroform Halogenated hydrocarbons such as bromoform, methyl iodide, dichloroethane, trichloroethane, trichloroethylene, chlorobenzene, o-dichlorobenzene, fluorobenzene, bromobenzene, iodobenzene, 1-chloronaphthalene Carbonization of medium, n-pentane, n-hexane, n-octane, 1,5-hexadiene, cyclohexane, methylcyclohexane, cyclohexadiene, benzene
- the press treatment step may be performed after the organic hole transport material is provided on the first electrode 2 provided with the electron transport material coated with the photosensitizing material.
- the press processing method is not particularly limited, and examples thereof include a press molding method using a flat plate represented by an IR tablet shaper, and a roll press method using a roller.
- the pressure in the press treatment is preferably 10 kgf / cm 2 or more, more preferably 30 kgf / cm 2 or more. Although there is no restriction
- a release material may be sandwiched between the press and the electrode.
- the release material include polytetrafluoroethylene, polychlorotrifluoride ethylene, tetrafluoroethylene hexafluoropropylene copolymer, perfluoroalkoxy fluoride resin, polyvinylidene fluoride, and ethylene tetrafluoride ethylene copolymer.
- fluororesins such as ethylene chlorotrifluoride ethylene copolymer and polyvinyl fluoride.
- a metal oxide may be provided between the organic hole transport material and the second electrode 7.
- the metal oxide include molybdenum oxide, tungsten oxide, vanadium oxide, nickel oxide, and the like. Among these, the molybdenum oxide is particularly preferable.
- the hole transport layer 6 may have a single layer structure made of a single material or a laminated structure made of a plurality of compounds.
- the laminated structure it is preferable to use a polymer material for the organic hole transport material layer close to the second electrode 7.
- the surface of the porous electron transport layer 4 can be further smoothed and the photoelectric conversion characteristics can be improved by using the polymer material having excellent film forming properties. Moreover, since it is difficult for the polymer material to penetrate into the porous electron transport layer 4, it is excellent in covering the surface of the porous electron transport layer 4. Therefore, higher performance can be obtained.
- the method for providing the metal oxide on the organic hole transport material is not particularly limited, and examples thereof include a method of forming a thin film in a vacuum such as sputtering or vacuum deposition, a wet film forming method, and the like.
- the wet film forming method is preferably a method in which a paste in which the metal oxide powder or sol is dispersed is prepared and applied onto the hole transport layer 6.
- the coating method is not particularly limited and can be performed according to a known method, for example, a dipping method, a spray method, a wire bar method, a spin coating method, a roller coating method, a blade coating method. Method, gravure coating method and the like. Various methods such as letterpress, offset, gravure, intaglio, rubber plate, and screen printing can be used as the wet printing method.
- the thickness of the second electrode is preferably 0.1 nm to 50 nm, and more preferably 1 nm to 10 nm.
- the second electrode 7 is newly applied after the hole transport layer 6 is formed or on the metal oxide.
- the second electrode 7 can be usually the same as the first electrode 2 described above, and a support is not necessarily required in a configuration in which strength and sealability are sufficiently maintained.
- Examples of the material of the second electrode 7 include metals such as platinum, gold, silver, copper, and aluminum, carbon compounds such as graphite, fullerene, carbon nanotube, and graphene, and conductive metal oxides such as ITO, FTO, and ATO. And conductive polymers such as polythiophene and polyaniline.
- the first electrode 2 and the second electrode 7 In order to operate as a dye-sensitized solar cell, at least one of the first electrode 2 and the second electrode 7 must be substantially transparent.
- a method in which the first electrode 2 side is transparent and sunlight is incident from the first electrode 2 side is preferable.
- a material that reflects light is preferably used on the second electrode 7 side, and a metal, glass, plastic, or metal thin film on which a conductive oxide is deposited is preferable. It is also effective to provide an antireflection layer on the sunlight incident side.
- the dye-sensitized solar cell of the present invention can be applied to a power supply device using a solar cell.
- any device can be used as long as it has conventionally used a solar cell or a power supply device using the solar cell.
- examples of utilizing the characteristics of the photoelectric conversion element of the present invention include a power supply device provided in a mobile phone, an electronic notebook, electronic paper, and the like. It can also be used as an auxiliary power source for extending the continuous use time of a rechargeable or dry battery type electric appliance.
- Example 1 (Production of titanium oxide semiconductor electrode) Mixing 2 ml of titanium tetra-n-propoxide, 4 ml of acetic acid, 1 ml of ion-exchanged water, and 40 ml of 2-propanol, spin-coating on an FTO glass substrate, drying at room temperature, baking in air at 450 ° C. for 30 minutes, A titanium oxide semiconductor electrode was produced. Using the same solution again, it was applied by spin coating on the obtained electrode so as to have a film thickness of 100 nm, and baked in air at 450 ° C. for 30 minutes to form a hole blocking layer.
- the titanium oxide semiconductor electrode is immersed in the Dye8 (0.5 mM, acetonitrile / t-butanol (volume ratio 1: 1) solution) as a sensitizing dye, and left to stand in a dark place for 1 hour to obtain a photosensitizing material. Adsorbed.
- Dye8 0.5 mM, acetonitrile / t-butanol (volume ratio 1: 1) solution
- an organic hole transport material (Merck Co., Ltd., brand: 2,2 ′, 7,7′-tetrakis (N, N-di-p-methoxyphenylamino) -9,9 '-Spirobifluorene, product number: SHT-263) dissolved in chlorobenzene (solid content: 14% by mass), lithium bis (trifluoromethanesulfonyl) imide (solid content: 1% by mass) manufactured by Kanto Chemical Co., Ltd., and exemplified basic compound No .
- a hole transport layer was formed by spin coating of a solution obtained by adding 1 (solid content of 1.4% by mass) on a semiconductor electrode carrying a photosensitizer. On this, silver was vacuum-deposited to a thickness of 100 nm to prepare a dye-sensitized solar cell.
- Example 2 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 3. The results are shown in Tables 2 and 3.
- Example 3 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion element was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 5 (basic compound). The results are shown in Tables 2 and 3.
- Example 4 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 8. The results are shown in Tables 2 and 3.
- Example 5 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 10. The results are shown in Tables 2 and 3.
- Example 6 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 12. The results are shown in Tables 2 and 3.
- Example 7 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 13. The results are shown in Tables 2 and 3.
- Example 8 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 15 basic compounds. The results are shown in Tables 2 and 3.
- Example 9 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 16 basic compounds. The results are shown in Tables 2 and 3.
- Example 10 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 18. The results are shown in Tables 2 and 3.
- Example 11 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion element was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 20 basic compounds. The results are shown in Tables 2 and 3.
- Example 12 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 13. The results are shown in Tables 2 and 3.
- Example 13 The dye in Example 1 is the dye of Dye8, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 13. The results are shown in Tables 2 and 3.
- Example 14 In the same manner as in Example 1, except that lithium bis (trifluoromethanesulfonyl) imide in Example 1 was changed to 1-n-hexyl-3-methylimidazolinium bis (trifluoromethylsulfonyl) imide. Sensitive solar cells were prepared and evaluated. The results are shown in Tables 2 and 3.
- Example 15 A dye-sensitized solar cell was prepared and evaluated in the same manner as in Example 1 except that the following hole transport layer was inserted between the hole transport layer and the silver electrode in Example 1. The results are shown in Tables 2 and 3.
- a solution obtained by adding 1-n-hexyl-3-methylimidazolinium trifluorosulfonyldiimide (27 mM) to chlorobenzene (solid content 2 mass%) in which poly (3-n-hexylthiophene) manufactured by Aldrich is dissolved was spray-coated on the hole transport layer to form a film of about 100 nm.
- Example 16 The dye in Example 1 is the dye of Dye8, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 21. The results are shown in Tables 2 and 3.
- Example 17 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 23. The results are shown in Tables 2 and 3.
- Example 18 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 24. The results are shown in Tables 2 and 3.
- Example 19 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 26. The results are shown in Tables 2 and 3.
- Example 20 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 28. The results are shown in Tables 2 and 3.
- Example 21 The basic compound in Example 1 was exemplified by Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 29. The results are shown in Tables 2 and 3.
- Example 22 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 26. The results are shown in Tables 2 and 3.
- Example 23 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 30. The results are shown in Tables 2 and 3.
- Example 24 The dye in Example 1 is the dye of Dye1, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 31. The results are shown in Tables 2 and 3.
- Example 25 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion element was produced and evaluated in the same manner as in Example 1 except that the basic compound was changed to 21. The results are shown in Tables 2 and 3.
- Example 26 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 26. The results are shown in Tables 2 and 3.
- Example 27 The dye in Example 1 is the dye of Dye4, the basic compound is Exemplified Compound No. A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound was changed to 28. The results are shown in Tables 2 and 3.
- Example 28 In the same manner as in Example 1, except that lithium bis (trifluoromethanesulfonyl) imide in Example 1 was changed to 1-n-hexyl-3-methylimidazolinium bis (trifluoromethylsulfonyl) imide. Sensitive solar cells were prepared and evaluated. The results are shown in Tables 2 and 3.
- Example 29 A dye-sensitized solar cell was prepared and evaluated in the same manner as in Example 16 except that the following hole transport layer was inserted between the hole transport layer and the silver electrode in Example 16. The results are shown in Tables 2 and 3.
- a solution obtained by adding 1-n-hexyl-3-methylimidazolinium trifluorosulfonyldiimide (27 mM) to chlorobenzene (solid content 2 mass%) in which poly (3-n-hexylthiophene) manufactured by Aldrich is dissolved was spray-coated on the hole transport layer to form a film of about 100 nm.
- Example 1 A photoelectric conversion device was prepared and evaluated in the same manner as in Example 1 except that the basic compound in Example 1 was changed to tarbutyl pyridine manufactured by Aldrich. The results are shown in Tables 2 and 3.
- the dye-sensitized solar cell of the present invention exhibits excellent photoelectric conversion characteristics.
- a photoelectric conversion element having a first electrode, a hole blocking layer, an electron transport layer, a first hole transport layer, and a second electrode Said 1st hole transport layer is a photoelectric conversion element characterized by including at least 1 among the basic compounds represented by the following general formula (1a) and general formula (1b).
- R 1 and R 2 represent a substituted or unsubstituted alkyl group or an aromatic hydrocarbon group, which may be the same or different, and R 1 and R 2 are And may be bonded to form a substituted or unsubstituted heterocyclic group containing a nitrogen atom.
- the electron transporting layer includes an electron transporting material photosensitized with a photosensitizing material represented by the following general formula (2).
- R 3 represents a substituted or unsubstituted alkyl group.
- the electron transporting material is at least one selected from titanium oxide, zinc oxide, tin oxide, and niobium oxide.
- the hole blocking layer includes titanium oxide.
- the first hole transport layer includes an ionic liquid.
- the ionic liquid includes an imidazolium compound.
- ⁇ 7> Any one of ⁇ 1> to ⁇ 6>, further including a second hole transport layer including a hole transporting polymer material between the first hole transport layer and the second electrode. It is a photoelectric conversion element as described in an item.
- a solar cell comprising the photoelectric conversion element according to any one of ⁇ 1> to ⁇ 7>.
- the first electrode, a hole blocking layer, an electron transport layer, a first hole transport layer, and a second electrode are provided.
- One hole transport layer uses at least one of the basic materials represented by the general formula (1a) or the general formula (1b), thereby increasing the internal resistance and the open circuit voltage. It is possible to obtain a solar cell with good characteristics in room light.
Abstract
Description
前記特許文献1及び前記非特許文献1及び2の前記色素増感型太陽電池は、酸化チタン等の金属酸化物半導体電極を多孔質化して表面積を大きくしたこと、並びに色素としてルテニウム錯体を単分子吸着させたことにより光電変換効率が著しく向上している。
1)無機半導体を用いたもの(例えば、非特許文献3、4参照)
2)低分子有機ホール輸送材料を用いたもの(例えば、特許文献2、非特許文献5、6参照)
3)導電性高分子を用いたもの(例えば、特許文献3、非特許文献7参照)
そこで、前記非特許文献4に記載の太陽電池においては、イミダゾリニウムチオシアナートを加えることによってヨウ化銅の結晶化を抑制しているが、十分ではない。
そのため、多孔質半導体の内部空孔へ前記トリフェニルアミン化合物が到達できず、低い変換効率しか得られていない。
しかしながら、この太陽電池におけるナノチタニア粒子膜厚の最適値は2μm程度とされており、ヨウ素電解液を使用する場合の10μm~20μmと比較して非常に薄い。そのため、酸化チタンに吸着した色素量も少なく、十分な光吸収やキャリア発生を行うことが困難であり、電解液を用いた場合の特性は及ばない。
また、従来のヨウ素等を用いた電解液型色素増感太陽電池は、アモルファスシリコン太陽電池以上に微弱な室内光における光電変換特性を有することが報告されている(非特許文献8参照)。
しかしながら、前記電解液型色素増感太陽電池は、上述したヨウ素と揮発性溶剤を含んでおり、ヨウ素レドックス系の劣化による発電効率の低下、電解液の揮発や漏れといった問題がある。
前記内部抵抗を高くすると短絡電流密度が悪くなり、光電変換特性悪化する。また、前記内部抵抗を低くすると開放電圧が悪くなり、光電変換特性が悪化する。すなわち、前記内部抵抗を高くすることと、良好な前記光電変換特性の両立は、非常に困難である。
すなわち、前記課題は、第一の電極と、ホールブロッキング層と、電子輸送層と、第一のホール輸送層と、第二の電極と、を有する光電変換素子であって、
前記第一のホール輸送層は、下記一般式(1a)及び一般式(1b)で表される塩基性化合物のうち少なくとも1つを含む光電変換素子により解決される。
なお、図1は光電変換素子及び太陽電池の積層方向に直交する断面を表す概略図の一例である。
図1に示す態様においては、基板1上に第一の電極2が設けられ、酸化チタンからなるホールブロッキング層3、電子輸送層4、電子輸送層上に光増感材料5が吸着し、第二の電極7との間にホール輸送層6を挟み込んだ構成をとっている。
第一の電極2としては、可視光に対して透明な導電性物質であれば特に限定されるものではなく、通常の光電変換素子、あるいは液晶パネル等に用いられる公知のものを使用できる。
第一の電極2は一定の硬性を維持するため、可視光に透明な材質からなる基板1上に設けることが好ましい。基板1としては、例えば、ガラス、透明プラスチック板、透明プラスチック膜、無機物透明結晶体などが用いられる。
これらは1種単独あるいは2種以上の混合、または積層したものでも構わない。また抵抗を下げる目的で、金属リード線等を併用してもよい。
ホールブロッキング層3としては、可視光に対して透明であり、かつ電子輸送性材料であれば特に限定されるものではないが、特に酸化チタンが好ましい。室内光等の弱い光でも使用可能にするために損失電流を抑制するには、高い内部抵抗を有することが必要であり、ホールブロッキング層3を形成する酸化チタンの製膜方法も重要である。
前記酸化チタンの製膜は一般的には、湿式製膜となるゾルゲル法や四塩化チタンからの加水分解法が挙げられるが、抵抗が低めである。乾式製膜となるスパッタリング法がより好ましい。
本発明の光電変換素子及び太陽電池は、ホールブロッキング層3上に多孔質状の電子輸送層4を形成するものであり、単層であっても多層であってもよい。
前記多層の場合、粒径の異なる半導体微粒子の分散液を多層塗布することも、種類の異なる半導体や、樹脂、添加剤の組成が異なる塗布層を多層塗布することもできる。
一度の塗布で厚みが不足する場合には、前記多層塗布は有効な手段である。
したがって、電子輸送層4の厚みは100nm~100μmが好ましい。
具体的には、シリコン、ゲルマニウムのような単体半導体、あるいは金属のカルコゲニドに代表される化合物半導体、またはペロブスカイト構造を有する化合物等を挙げることができる。
前記金属の前記カルコゲニドとしては、例えば、チタン、スズ、亜鉛、鉄、タングステン、ジルコニウム、ハフニウム、ストロンチウム、インジウム、セリウム、イットリウム、ランタン、バナジウム、ニオブ、あるいはタンタルの酸化物、カドミウム、亜鉛、鉛、銀、アンチモン、ビスマスの硫化物、カドミウム、鉛のセレン化物、カドミウムのテルル化物等が挙げられる。
他の化合物半導体としては、例えば、亜鉛、ガリウム、インジウム、カドミウム、等のリン化物、ガリウム砒素、銅-インジウム-セレン化物、銅-インジウム-硫化物等が挙げられる。
前記ペロブスカイト構造を有する化合物としては、例えば、チタン酸ストロンチウム、チタン酸カルシウム、チタン酸ナトリウム、チタン酸バリウム、ニオブ酸カリウム等が挙げられる。これらは、1種単独、あるいは2種以上の混合で使用しても構わない。
これらの中でも、酸化物半導体が好ましく、酸化チタン、酸化亜鉛、酸化スズ、酸化ニオブが特に好ましい。これらの半導体の結晶型は特に限定されるものではなく、単結晶でも多結晶でも、あるいは非晶質でも構わない。
また、より大きい平均粒径の半導体粒子を混合あるいは積層して入射光を散乱させる効果により、効率を向上させることも可能である。この場合の前記半導体粒子の平均粒径は50nm~500nmが好ましい。
前記湿式製膜法を用いた場合、塗布方法については、特に制限はなく、公知の方法にしたがって行うことができ、例えば、ディップ法、スプレー法、ワイヤーバー法、スピンコート法、ローラーコート法、ブレードコート法、グラビアコート法などが挙げられる。また、湿式印刷方法としては、例えば、凸版、オフセット、グラビア、凹版、ゴム版、スクリーン印刷等の様々な方法を用いることができる。
前記増粘剤としては、例えば、ポリエチレングリコール、ポリビニルアルコール等の高分子、エチルセルロース等の増粘剤等が挙げられる。
照射時間には特に制限がないが、1時間以内で行うことが好ましい。
本発明では変換効率のさらなる向上のため、光増感材料を電子輸送層4である電子輸送性半導体の表面に吸着させる。前記光増感材料としては一般式(2)に示すものが好ましい。
Dye1 R3=CH2CH3(日本科学物質辞書番号:J2.477.478C、J3.081.465G)
Dye2 R3=(CH2)3CH3
Dye3 R3=C(CH3)3
Dye4 R3=(CH2)9CH3
Dye5 R3=(CH2)2COOH
Dye6 R3=(CH2)4COOH
Dye7 R3=(CH2)7COOH
Dye8 R3=(CH2)10COOH(日本科学物質辞書番号:J3.113.583D)
特表平7-500630号公報、特開平10-233238号公報、特開2000-26487号公報、特開2000-323191号公報、特開2001-59062号公報等に記載の金属錯体化合物、特開平10-93118号公報、特開2002-164089号公報、特開2004-95450号公報、J.Phys.Chem.C,7224,Vol.111(2007)等に記載のクマリン化合物、特開2004-95450号公報、Chem.Commun.,4887(2007)等に記載のポリエン化合物、特開2003-264010号公報、特開2004-63274号公報、特開2004-115636号公報、特開2004-200068号公報、特開2004-235052号公報、J.Am.Chem.Soc.,12218,Vol.126(2004)、Chem.Commun.,3036(2003)、Angew.Chem.Int.Ed.,1923,Vol.47(2008)等に記載のインドリン化合物、J.Am.Chem.Soc.,16701,Vol.128(2006)、J.Am.Chem.Soc.,14256,Vol.128(2006)等に記載のチオフェン化合物、特開平11-86916号公報、特開平11-214730号公報、特開2000-106224号公報、特開2001-76773号公報、特開2003-7359号公報等に記載のシアニン色素、特開平11-214731号公報、特開平11-238905号公報、特開2001-52766号公報、特開2001-76775号公報、特開2003-7360号公報等に記載のメロシアニン色素、特開平10-92477号公報、特開平11-273754号公報、特開平11-273755号公報、特開2003-31273号公報等に記載の9-アリールキサンテン化合物、特開平10-93118号公報、特開2003-31273号公報等に記載のトリアリールメタン化合物、特開平9-199744号公報、特開平10-233238号公報、特開平11-204821号公報、特開平11-265738号公報、J.Phys.Chem.,2342,Vol.91(1987)、J.Phys.Chem.B,6272,Vol.97(1993)、Electroanal.Chem.,31,Vol.537(2002)、特開2006-032260号公報、J.Porphyrins Phthalocyanines,230,Vol.3(1999)、Angew.Chem.Int.Ed.,373,Vol.46(2007)、Langmuir,5436,Vol.24(2008)等に記載のフタロシアニン化合物、ポルフィリン化合物等を挙げることができる。
これらの中でも、前記金属錯体化合物、前記クマリン化合物、前記ポリエン化合物、前記インドリン化合物、前記チオフェン化合物が好ましい。
前記溶液あるいは分散液を電子輸送層に塗布して吸着させる方法としては、例えば、ワイヤーバー法、スライドホッパー法、エクストルージョン法、カーテン法、スピン法、スプレー法等を用いることができる。
また、二酸化炭素などを用いた超臨界流体中で吸着させても構わない。
前記縮合剤としては、無機物表面に物理的あるいは化学的に光増感材料と電子輸送化合物を結合すると思われる触媒的作用をするもの、または化学量論的に作用し、化学平衡を有利に移動させるものの何れであってもよい。
さらに、前記縮合助剤としてチオールやヒドロキシ化合物を添加してもよい。
前記凝集解離剤の添加量は、色素1質量部に対して0.01質量部~500質量部が好ましく、0.1質量部~100質量部がより好ましい。
また、この吸着は静置しても攪拌しながら行なっても構わない。
また、前記吸着は暗所で行なうことが好ましい。
ホール輸送材料6としては、有機ホール輸送材料、及び一般式(1a)又は一般式(1b)で表される塩基性化合物のうち少なくとも1つを含有していれば、特に制限はなく、目的に応じて適宜選択することができる。
なお、一般的なホール輸送層としては、酸化還元対を有機溶媒に溶解した電解液、酸化還元対を有機溶媒に溶解した液体をポリマーマトリックスに含浸したゲル電解質、酸化還元対を含有する溶融塩、固体電解質、無機ホール輸送材料、有機ホール輸送材料等が用いられる。
前記有機ホール輸送材料としては、単一材料からなる単層構造のホール輸送層6、又は複数の化合物からなる積層構造のホール輸送層6のいずれにも用いることができる。
その具体例としては特公昭34-5466号公報等に示されているオキサジアゾール化合物、特公昭45-555号公報等に示されているトリフェニルメタン化合物、特公昭52-4188号公報等に示されているピラゾリン化合物、特公昭55-42380号公報等に示されているヒドラゾン化合物、特開昭56-123544号公報等に示されているオキサジアゾール化合物、特開昭54-58445号公報に示されているテトラアリールベンジジン化合物、特開昭58-65440号公報あるいは特開昭60-98437号公報に示されているスチルベン化合物、Adv.Mater.,813,vol.17,(2005)記載のspiro-OMeTADなどのスピロビフルオレン系化合物等を挙げることができる。
これらの中でも、前記spiro-OMeTADと称されるホール輸送材料が優れた光電変換特性を示す点で好ましい。
その具体例としては、ポリ(3-n-ヘキシルチオフェン)、ポリ(3-n-オクチルオキシチオフェン)、ポリ(9,9’-ジオクチル-フルオレン-コ-ビチオフェン)、ポリ(3,3’’’-ジドデシル-クォーターチオフェン)、ポリ(3,6-ジオクチルチエノ[3,2-b]チオフェン)、ポリ(2,5-ビス(3-デシルチオフェン-2-イル)チエノ[3,2-b]チオフェン)、ポリ(3,4-ジデシルチオフェン-コ-チエノ[3,2-b]チオフェン)、ポリ(3,6-ジオクチルチエノ[3,2-b]チオフェン-コ-チエノ[3,2-b]チオフェン)、ポリ(3,6-ジオクチルチエノ[3,2-b]チオフェン-コ-チオフェン)、ポリ(3.6-ジオクチルチエノ[3,2-b]チオフェン-コ-ビチオフェン)等のポリチオフェン化合物、
ポリ[2-メトキシー5-(2-エチルヘキシルオキシ)-1,4-フェニレンビニレン]、ポリ[2-メトキシー5-(3,7-ジメチルオクチルオキシ)-1,4-フェニレンビニレン]、ポリ[(2-メトキシ-5-(2-エチルフェキシルオキシ)-1,4-フェニレンビニレン)-コ-(4,4’-ビフェニレンービニレン)]等のポリフェニレンビニレン化合物、
ポリ(9,9’-ジドデシルフルオレニル-2,7-ジイル)、ポリ[(9,9-ジオクチル-2,7-ジビニレンフルオレン)-alt-コ-(9,10-アントラセン)]、ポリ[(9,9-ジオクチル-2,7-ジビニレンフルオレン)-alt-コ-(4,4’-ビフェニレン)]、ポリ[(9,9-ジオクチル-2,7-ジビニレンフルオレン)-alt-コ-(2-メトキシ-5-(2-エチルヘキシルオキシ)-1,4-フェニレン)]、ポリ[(9,9-ジオクチル-2,7-ジイル)-コ-(1,4-(2,5-ジヘキシルオキシ)ベンゼン)]等のポリフルオレン化合物、
ポリ[2,5-ジオクチルオキシ-1,4-フェニレン]、ポリ[2,5-ジ(2-エチルヘキシルオキシー1,4-フェニレン]等のポリフェニレン化合物、
ポリ[(9,9-ジオクチルフルオレニル-2,7-ジイル)-alt-コ-(N,N’-ジフェニル)-N,N’-ジ(p-ヘキシルフェニル)-1,4-ジアミノベンゼン]、ポリ[(9,9-ジオクチルフルオレニル-2,7-ジイル)-alt-コ-(N,N’-ビス(4-オクチルオキシフェニル)ベンジジン-N,N’-(1,4-ジフェニレン)]、ポリ[(N,N’-ビス(4-オクチルオキシフェニル)ベンジジン-N,N’-(1,4-ジフェニレン)]、ポリ[(N,N’-ビス(4-(2-エチルヘキシルオキシ)フェニル)ベンジジン-N,N’-(1,4-ジフェニレン)]、ポリ[フェニルイミノ-1,4-フェニレンビニレン-2,5-ジオクチルオキシ-1,4-フェニレンビニレン-1,4-フェニレン]、ポリ[p-トリルイミノ-1,4-フェニレンビニレン-2,5-ジ(2-エチルヘキシルオキシ)-1,4-フェニレンビニレン-1,4-フェニレン]、ポリ[4-(2-エチルヘキシルオキシ)フェニルイミノ-1,4-ビフェニレン]等のポリアリールアミン化合物、
ポリ[(9,9-ジオクチルフルオレニル-2,7-ジイル)-alt-コ-(1,4-ベンゾ(2,1’,3)チアジアゾール]、ポリ(3,4-ジデシルチオフェン-コ-(1,4-ベンゾ(2,1’,3)チアジアゾール)等のポリチアジアゾール化合物を挙げることができる。
これらの中でも、キャリア移動度やイオン化ポテンシャルを考慮すると前記ポリチオフェン化合物と前記ポリアリールアミン化合物が特に好ましい。
前記添加剤としては、例えば、ヨウ素、ヨウ化リチウム、ヨウ化ナトリウム、ヨウ化カリウム、ヨウ化セシウム、ヨウ化カルシウム、ヨウ化銅、ヨウ化鉄、ヨウ化銀等の金属ヨウ化物、
ヨウ化テトラアルキルアンモニウム、ヨウ化ピリジニウム等の4級アンモニウム塩、臭化リチウム、臭化ナトリウム、臭化カリウム、臭化セシウム、臭化カルシウム等の金属臭化物、
臭化テトラアルキルアンモニウム、臭化ピリジニウム等の4級アンモニウム化合物の臭素塩、
塩化銅、塩化銀等の金属塩化物、酢酸銅、酢酸銀、酢酸パラジウム等の酢酸金属塩、
硫酸銅、硫酸亜鉛等の金属硫酸塩、フェロシアン酸塩-フェリシアン酸塩、フェロセン-フェリシニウムイオン等の金属錯体、
ポリ硫化ナトリウム、アルキルチオール-アルキルジスルフィド等のイオウ化合物、
ビオロゲン色素、ヒドロキノン等、ヨウ化1,2-ジメチル-3-n-プロピルイミダゾイニウム塩、ヨウ化1-メチル-3-n-ヘキシルイミダゾリニウム塩、1,2-ジメチル-3-エチルイミダゾリウムトリフロオロメタンスルホン酸塩、1-メチル-3-ブチルイミダゾリウムノナフルオロブチルスルホン酸塩、1-メチル-3-エチルイミダゾリウムビス(トリフルオロメチル)スルホニルイミド等のInorg.Chem.35(1996)1168に記載のイオン液体、ピリジン、4-t-ブチルピリジン、ベンズイミダゾール等の塩基性化合物、
リチウムトリフルオロメタンスルホニルイミド、リチウムジイソプロピルイミド等のリチウム化合物などが挙げられる。
本発明においては、前記有機ホール輸送材料に下記一般式(1a)又は一般式(1b)で表される塩基性化合物を添加することで、特に高い開放電圧を得ることができる。
また、光電変換素子における内部抵抗が高まり、室内光等の微弱光における損失電流を低減することができる。よって、従来の塩基性化合物より高い開放電圧を得られる。
したがって、短絡電流密度の低下量が少なく、高い開放電圧が得られることで、優れた光電変換特性を得ることができる。さらに、報告例が少ない室内光等の微弱光における光電変換する際に、特に際立って優位性が現れることを検証することができた。
報告例(J.Org.Chem., 67 (2002) 3029)同様に下記ルートから容易に合成することができる。
前記酸化剤としては、例えば、ヘキサクロロアンチモン酸トリス(4-ブロモフェニル)アミニウム、ヘキサフルオロアンチモネート銀、ニトロソニウムテトラフルオボラート、硝酸銀、コバルト錯体系化合物等が挙げられる。
前記超臨界流体は、気体と液体が共存できる限界(臨界点)を超えた温度・圧力領域において非凝集性高密度流体として存在し、圧縮しても凝集せず、臨界温度以上、かつ臨界圧力以上の状態にある流体である限り特に制限はなく、目的に応じて適宜選択することができるが、臨界温度が低いものが好ましい。
また、これらの流体は、1種単独であっても二種以上の混合であっても構わない。
前記超臨界流体として挙げられる化合物は、前記亜臨界流体としても好適に使用することができる。
前記有機溶媒及び前記エントレーナーの添加により、前記超臨界流体中での溶解度の調整をより容易に行うことができる。
前記プレス処理方法としては、特に制限はないが、例えば、IR錠剤整形器に代表されるような平板を用いたプレス成型法、ローラなどを用いたロールプレス法などが挙げられる。
また、前記プレス処理時に熱を加えても構わない。
前記離型材としては、例えば、ポリ四フッ化エチレン、ポリクロロ三フッ化エチレン、四フッ化エチレン六フッ化プロピレン共重合体、ペルフルオロアルコキシフッ化樹脂、ポリフッ化ビニリデン、エチレン四フッ化エチレン共重合体、エチレンクロロ三フッ化エチレン共重合体、ポリフッ化ビニルなどのフッ素樹脂などが挙げられる。
また、前記高分子材料は多孔質状の電子輸送層4内部へ浸透することが困難であるため、逆に多孔質状の電子輸送層4表面の被覆にも優れ、電極を設ける際の短絡防止にも効果を発揮するため、より高い性能を得ることが可能となる。
前記金属酸化物を前記有機ホール輸送材料上に設ける方法としては、特に制限はなく、スパッタリングや真空蒸着等の真空中で薄膜を形成する方法や湿式成膜法などが挙げられる。
前記湿式成膜法を用いた場合、塗布方法は特に制限はなく、公知の方法にしたがって行なうことができ、例えば、ディップ法、スプレー法、ワイヤーバー法、スピンコート法、ローラーコート法、ブレードコート法、グラビアコート法などが挙げられる。また、湿式印刷方法として、凸版、オフセット、グラビア、凹版、ゴム版、スクリーン印刷等様々な方法を用いることができる。前記第二の電極の厚みとしては、0.1nm~50nmが好ましく、1nm~10nmがより好ましい。
第二の電極7は、通常前述の第一の電極2と同様のものを用いることができ、強度や密封性が充分に保たれるような構成では支持体は必ずしも必要ではない。
第二の電極7の塗設については、用いられる材料の種類やホール輸送層6の種類により、適宜ホール輸送層6上に塗布、ラミネート、蒸着、CVD、貼り合わせ等の手法により形成可能である。
本発明の色素増感型太陽電池においては、第一の電極2側が透明であり、太陽光を第一の電極2側から入射させる方法が好ましい。この場合、第二の電極7側には光を反射させる材料を使用することが好ましく、金属、導電性酸化物を蒸着したガラス、プラスチック、あるいは金属薄膜が好ましい。
また、太陽光の入射側に反射防止層を設けることも有効な手段である。
本発明の色素増感型太陽電池は、太陽電池を用いた電源装置に応用できる。
応用例としては、従来から太陽電池やそれを用いた電源装置を利用している機器類であれば、いずれのものでも可能である。
(酸化チタン半導体電極の作製)
チタニウムテトラ-n-プロポキシド2ml、酢酸4ml、イオン交換水1ml、及び2-プロパノール40mlを混合し、FTOガラス基板上にスピンコートし、室温で乾燥後、空気中450℃で30分間焼成し、酸化チタン半導体電極を作製した。
再度同一溶液を用いて、得た電極上に膜厚100nmになるようにスピンコートで塗布し、空気中450℃で30分間焼成してホールブロッキング層を形成した。
得られた分散液にポリエチレングリコール(#20,000)1.2gを加えてペーストを作製した。
このペーストを、上記ホールブロッキング層上に厚み1.5μmになるように塗布し、室温で乾燥後、空気中500℃で30分間焼成し、多孔質状の電子輸送層を形成した。
上記酸化チタン半導体電極を、増感色素として前記Dye8(0.5mM、アセトニトリル/t-ブタノール(体積比1:1)溶液)に浸漬し、1時間暗所にて静置し光増感材料を吸着させた。
光増感剤を担持した半導体電極上に、有機ホール輸送材料(メルク株式会社製、銘柄:2,2’,7,7’-tetrakis(N,N-di-p-methoxyphenylamino)-9,9’-spirobifluorene、品番:SHT-263)を溶解したクロロベンゼン(固形分14質量%)溶液に、関東化学社製リチウムビス(トリフルオロメタンスルホニル)イミド(固形分1質量%)、及び例示塩基性化合物No.1(固形分1.4質量%)を加えて得た溶液を、光増感剤を担持した半導体電極上にスピンコートにてホール輸送層を成膜した。この上に銀を厚み100nmに真空蒸着して色素増感型太陽電池を作製した。
得られた色素増感型太陽電池の白色LED照射下(0.05mW/cm2)における光電変換効率を測定した。白色LEDはコスモテクノ社製デスクランプCDS-90α(スタディーモード)、評価機器はNF回路設計ブロック社製太陽電池評価システムAs-510-PV03にて測定した。その結果、開放電圧=0.82V、短絡電流密度8.20μA/cm2、形状因子=0.78、変換効率=10.48%という優れた特性を示した。
実施例1における塩基性化合物を例示化合物No.3の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.5の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.8の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.10の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.12の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.13の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.15の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.16の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.18の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.20の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.13の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye8の色素に、塩基性化合物を例示化合物No.13の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における、リチウムビス(トリフルオロメタンスルホニル)イミドを1-n-ヘキシル-3-メチルイミダゾリニウムビス(トリフルオロメチルスルホニル)イミドに変更した以外は、実施例1と同様にして、色素増感型太陽電池を作製し、評価した。結果を表2及び表3に示した。
実施例1における、ホール輸送層と銀電極の間に、下記ホール輸送層を挿入した以外は、実施例1と同様にして、色素増感型太陽電池を作製し、評価した。結果を表2及び表3に示した。
アルドリッチ社製ポリ(3-n-ヘキシルチオフェン)を溶解したクロロベンゼン(固形分2質量%)に、1-n-ヘキシル-3-メチルイミダゾリニウムトリフルオロスルホニルジイミド(27mM)を加えて得た溶液をホール輸送層上にスプレー塗布して約100nm製膜した。
実施例1における色素をDye8の色素に、塩基性化合物を例示化合物No.21の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.23の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.24の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.26の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.28の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における塩基性化合物を例示化合物No.29の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.26の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.30の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye1の色素に、塩基性化合物を例示化合物No.31の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.21の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.26の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における色素をDye4の色素に、塩基性化合物を例示化合物No.28の塩基性化合物に変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
実施例1における、リチウムビス(トリフルオロメタンスルホニル)イミドを1-n-ヘキシル-3-メチルイミダゾリニウムビス(トリフルオロメチルスルホニル)イミドに変更した以外は、実施例1と同様にして、色素増感型太陽電池を作製し、評価した。結果を表2及び表3に示した。
実施例16における、ホール輸送層と銀電極の間に、下記ホール輸送層を挿入した以外は、実施例16と同様にして、色素増感型太陽電池を作製し、評価した。結果を表2及び表3に示した。
アルドリッチ社製ポリ(3-n-ヘキシルチオフェン)を溶解したクロロベンゼン(固形分2質量%)に、1-n-ヘキシル-3-メチルイミダゾリニウムトリフルオロスルホニルジイミド(27mM)を加えて得た溶液をホール輸送層上にスプレー塗布して約100nm製膜した。
実施例1における塩基性化合物を、アルドリッチ社製ターシャルブチルピリジンに変更した以外は、実施例1と同様にして、光電変換素子を作製し、評価した。結果を表2及び表3に示した。
<1> 第一の電極と、ホールブロッキング層と、電子輸送層と、第一のホール輸送層と、第二の電極と、を有する光電変換素子であって、
前記第一のホール輸送層は、下記一般式(1a)及び一般式(1b)で表される塩基性化合物のうち少なくとも1つを含むことを特徴とする光電変換素子である。
<2> 前記電子輸送層は、下記一般式(2)で表される光増感材料で光増感された電子輸送性材料を含む前記<1>に記載の光電変換素子である。
<3> 前記電子輸送性材料が、酸化チタン、酸化亜鉛、酸化スズ、及び酸化ニオブから選択される少なくとも1種である前記<2>に記載の光電変換素子である。
<4> 前記ホールブロッキング層は、酸化チタンを含むことを特徴とする前記<1>乃至<3>のいずれか一項に記載の光電変換素子である。
<5> 前記第一のホール輸送層は、イオン液体を含む前記<1>乃至<4>のいずれか一項に記載の光電変換素子である。
<6> 前記イオン液体は、イミダゾリウム化合物を含む前記<5>に記載の光電変換素子である。
<7> 前記第一のホール輸送層と前記第二の電極との間に、ホール輸送性の高分子材料を含む第二のホール輸送層を有する前記<1>乃至<6>のいずれか一項に記載の光電変換素子である。
<8> 前記<1>乃至<7>のいずれか一項に記載の光電変換素子を具備することを特徴とする太陽電池である。
前記<8>記載の「太陽電池」によれば、第一の電極と、ホールブロッキング層と、電子輸送層と、第一のホール輸送層と、第二の電極と、を有し、前記第一のホール輸送層は、前記一般式(1a)又は一般式(1b)で表される塩基性材料のうち少なくとも1を用いたものであることにより、内部抵抗及び開放電圧が高くなることで、室内光における良好な特性の太陽電池を得ることが可能である。
2 第一の電極定着装置
3 ホールブロッキング層
4 電子輸送層
5 光増感化合物
6 ホール輸送層
7 第二の電極
8 リードライン
9 リードライン
Claims (8)
- 前記電子輸送性材料が、酸化チタン、酸化亜鉛、酸化スズ、及び酸化ニオブから選択される少なくとも1種である請求項2に記載の光電変換素子。
- 前記ホールブロッキング層は、酸化チタンを含む請求項1乃至3のいずれか一項に記載の光電変換素子。
- 前記第一のホール輸送層は、イオン液体を含む請求項1乃至4のいずれか一項に記載の光電変換素子。
- 前記イオン液体は、イミダゾリウム化合物を含む請求項5に記載の光電変換素子。
- 前記第一のホール輸送層と前記第二の電極との間に、ホール輸送性の高分子材料を含む第二のホール輸送層を有する請求項1乃至6のいずれか一項に記載の光電変換素子。
- 請求項1乃至7のいずれか一項に記載の光電変換素子を具備することを特徴とする太陽電池。
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KR102112330B1 (ko) | 2020-05-19 |
US20200273630A1 (en) | 2020-08-27 |
JP2019083324A (ja) | 2019-05-30 |
KR20160124186A (ko) | 2016-10-26 |
JP2021005723A (ja) | 2021-01-14 |
JPWO2015125587A1 (ja) | 2017-03-30 |
CN110690350A (zh) | 2020-01-14 |
EP3113240A4 (en) | 2017-03-15 |
EP3113240A1 (en) | 2017-01-04 |
KR20200056470A (ko) | 2020-05-22 |
US10636579B2 (en) | 2020-04-28 |
EP3113240B1 (en) | 2024-04-03 |
CN106062985A (zh) | 2016-10-26 |
US20170069431A1 (en) | 2017-03-09 |
US11101080B2 (en) | 2021-08-24 |
JP6520914B2 (ja) | 2019-05-29 |
KR20210073610A (ko) | 2021-06-18 |
KR102330122B1 (ko) | 2021-11-24 |
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