WO2012057325A1 - 光電変換素子用電解質ならびにその電解質を用いた光電変換素子および色素増感太陽電池 - Google Patents
光電変換素子用電解質ならびにその電解質を用いた光電変換素子および色素増感太陽電池 Download PDFInfo
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- WO2012057325A1 WO2012057325A1 PCT/JP2011/074949 JP2011074949W WO2012057325A1 WO 2012057325 A1 WO2012057325 A1 WO 2012057325A1 JP 2011074949 W JP2011074949 W JP 2011074949W WO 2012057325 A1 WO2012057325 A1 WO 2012057325A1
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- photoelectric conversion
- electrolyte
- conversion element
- dye
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- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- NZINNJYWGLAHPB-UHFFFAOYSA-N tributyl(methoxy)silane Chemical compound CCCC[Si](CCCC)(CCCC)OC NZINNJYWGLAHPB-UHFFFAOYSA-N 0.000 description 1
- ZCVOUFBEEYGNOL-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl ZCVOUFBEEYGNOL-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RQPWVAXZWDTDPH-UHFFFAOYSA-N tridodecyl(methyl)azanium Chemical compound CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC RQPWVAXZWDTDPH-UHFFFAOYSA-N 0.000 description 1
- FZXOVEZAKDRQJC-UHFFFAOYSA-N triethoxy(nonyl)silane Chemical compound CCCCCCCCC[Si](OCC)(OCC)OCC FZXOVEZAKDRQJC-UHFFFAOYSA-N 0.000 description 1
- ZJLGWINGXOQWDC-UHFFFAOYSA-N triethoxy(pentadecyl)silane Chemical compound CCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC ZJLGWINGXOQWDC-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- IMAMKGXMSYGEGR-UHFFFAOYSA-N triethoxy(tridecyl)silane Chemical compound CCCCCCCCCCCCC[Si](OCC)(OCC)OCC IMAMKGXMSYGEGR-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- CUIGTYKJLRVARY-UHFFFAOYSA-N triethyl(hexyl)phosphanium Chemical compound CCCCCC[P+](CC)(CC)CC CUIGTYKJLRVARY-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- DWFJNCCEVKAUSF-UHFFFAOYSA-N triheptyl(methoxy)silane Chemical compound CCCCCCC[Si](CCCCCCC)(CCCCCCC)OC DWFJNCCEVKAUSF-UHFFFAOYSA-N 0.000 description 1
- KGYMEAMMTCVOSR-UHFFFAOYSA-N trihexyl(methoxy)silane Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)OC KGYMEAMMTCVOSR-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/035—Liquid electrolytes, e.g. impregnating materials
-
- 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
- H01G9/2009—Solid electrolytes
-
- 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
-
- 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
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
-
- 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
Definitions
- the present invention relates to an electrolyte for a photoelectric conversion element, a photoelectric conversion element using the electrolyte, and a dye-sensitized solar cell.
- dye-sensitized solar cells developed by Grezel, etc. of Switzerland have high photoelectric conversion efficiency among solar cells using organic materials, and are less expensive to manufacture than silicon-based solar cells. It is also attracting attention as a new type of solar cell due to its advantages such as low price.
- dye-sensitized solar cells are electrochemical cells, organic electrolytes or ionic liquids are used as electrolytes. When organic electrolytes are used, they may volatilize or be depleted during long-term use. However, when using ionic liquids, volatilization and depletion during long-term use can be prevented, but there are durability problems such as structural deterioration due to liquid leakage. It was. In view of this, studies have been made to change the electrolyte from liquid to gel or solid for the purpose of preventing volatilization and leakage of the electrolyte and ensuring long-term stability and durability of the solar cell.
- Patent Document 1 describes "(i) Layered clay mineral and / or organically modified layered clay mineral and (ii) an electrolyte for a photoelectric conversion element comprising an ionic liquid.” 1]).
- an object of the present invention is to provide an electrolyte for a photoelectric conversion element that can achieve excellent moisture resistance, a photoelectric conversion element using the electrolyte, and a dye-sensitized solar cell.
- the present invention provides the following (a) to (g).
- An electrolyte for a photoelectric conversion element comprising an organic solvent (A) and a layered clay mineral (B),
- the electrolyte for photoelectric conversion elements whose boiling point of the said organic solvent (A) is 150 degreeC or more, and whose dielectric constant is 20 or more.
- R 1 represents a hydrocarbon group that may contain a heteroatom having 1 to 20 carbon atoms, and has a substituent that may contain a heteroatom having 1 to 20 carbon atoms. May be.
- R 2 and R 3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and may contain a hetero atom. However, when the nitrogen atom contains a double bond, R 3 does not exist.
- Q represents a nitrogen atom, an oxygen atom, a phosphorus atom or a sulfur atom
- R 4 , R 5 , R 6 and R 7 are each independently a hydrogen atom or a hydrocarbon having 1 to 8 carbon atoms. Represents a group and may contain a heteroatom. However, when Q is an oxygen atom or a sulfur atom, R 7 does not exist, and when Q is a sulfur atom, R 4 and R 5 may be linked.
- an electrolyte for a photoelectric conversion element that can achieve excellent moisture resistance, a photoelectric conversion element using the electrolyte, and a dye-sensitized solar cell.
- a photoelectric conversion element using the electrolyte and a dye-sensitized solar cell.
- the dye-sensitized solar cell of the present invention is excellent in moisture resistance, it can be applied, for example, in a use environment where it is exposed to outside air in which humidity varies greatly, and is very useful.
- FIG. 1 is a schematic cross-sectional view showing an example of the basic configuration of the photoelectric conversion element of the present invention.
- FIG. 2 is a drawing showing the basic configuration of the dye-sensitized solar cell of the present invention used in Examples and the like.
- the electrolyte for photoelectric conversion elements of the present invention (hereinafter also simply referred to as “the electrolyte of the present invention”) is an electrolyte for photoelectric conversion elements containing an organic solvent (A) and a layered clay mineral (B), It is an electrolyte for a photoelectric conversion element having a boiling point of the solvent (A) of 150 ° C. or higher and a relative dielectric constant of 20 or higher. Moreover, it is preferable that the electrolyte of this invention contains the organic salt compound (C) which has a tertiary or quaternary cation from a viewpoint of suppressing volatilization and improving the stability of a photoelectrode.
- the organic salt compound (C) which has a tertiary or quaternary cation from a viewpoint of suppressing volatilization and improving the stability of a photoelectrode.
- the organic solvent (A) used for the electrolyte of the present invention is not particularly limited as long as the organic solvent has a boiling point of 150 ° C. or higher and a relative dielectric constant of 20 or higher.
- the boiling point refers to the boiling point at 1 atm
- the relative dielectric constant is measured using a liquid dielectric constant meter (liquid dielectric constant meter M-870, manufactured by Nippon Lucas Co., Ltd.) to which 25 ° C. and 10 kHz are applied. Value.
- organic solvent (A) examples include methoxypropionitrile (boiling point: 166 ° C., relative dielectric constant: 25), ethoxypropionitrile (boiling point: 171 ° C., relative dielectric constant: 22), Butoxypropionitrile (boiling point: 206 ° C., relative dielectric constant: 20), dimethoxypropionitrile (boiling point: 195 ° C., relative dielectric constant: 28), glutaronitrile (boiling point: 286 ° C., relative dielectric constant: 20), Ethylene glycol bis (propionitrile) ether (boiling point: 330 ° C., relative dielectric constant: 20), propylene carbonate (boiling point: 240 ° C., relative dielectric constant: 65), diethyl carbonate (boiling point: 240 ° C., relative dielectric constant: 65) ), Ethyl methyl carbonate (boiling point: 166
- cyclic carbonates which are high dielectric constant solvents such as ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, ethyl-n-butyl carbonate
- chain carbonates which are low viscosity solvents such as methyl-t-butyl carbonate, di-i-propyl carbonate, t-butyl-i-propyl carbonate and the like may be mixed appropriately as long as the object of the present invention is not impaired. .
- methoxypropionitrile and ethoxypropionitrile are preferred because the photoelectric conversion efficiency of the photoelectric conversion element using the electrolyte of the present invention (hereinafter also referred to as “the photoelectric conversion element of the present invention”) is improved.
- Butoxypropionitrile is preferably used, and propylene carbonate, diethyl carbonate, ethyl methyl carbonate, and ⁇ -butyrolactone are preferable because they are easily available and inexpensive. Generation of cracked gas is preferable.
- ethyl isopropyl sulfone, sulfolane, and methyl sulfolane are preferred.
- the photoelectric conversion element which has the outstanding moisture resistance can be formed by containing such an organic solvent (A).
- the organic solvent (A) is less hygroscopic than the ionic liquid, is less volatile during long-term use, and is highly soluble in other electrolyte components. This is probably because of this.
- the layered clay mineral (B) described later is dispersed in the organic solvent (A), it is possible to suppress the intrusion of water vapor in the atmosphere, and further to the electrolyte layer of the photoelectric conversion element of the present invention.
- the content of the organic solvent (A) is preferably 50 to 95% by mass and more preferably 55 to 90% by mass with respect to the total mass of the electrolyte of the present invention. . When the content is within this range, the photoelectric conversion efficiency of the photoelectric conversion element of the present invention becomes better.
- the layered clay mineral (B) used in the electrolyte of the present invention is not particularly limited, but is preferably a phyllosilicate in which a silicate tetrahedron is bound in a two-dimensional sheet, and specific examples thereof include montmorillonite, bentonite, and saponite. , Smectite clay minerals such as beidellite, nontronite, hectorite, and stevensite; vermiculite clay minerals such as vermiculite; mica clay minerals such as muskite, flocovite, mica, etc. You may use independently and may use 2 or more types together. Moreover, the layered clay mineral (B) used for the electrolyte of the present invention may be a natural product or a synthetic product.
- the cation exchange capacity of the layered clay mineral is preferably 10 to 300 meq / 100 g.
- the layered clay mineral (B) such as natural montmorillonite (trade name: Kunipia F, average particle size: 0.1 to 1 ⁇ m, manufactured by Kunimine Kogyo Co., Ltd.), synthetic smectite (product) Name: Smecton SA, average particle size: 20 nm, manufactured by Kunimine Kogyo Co., Ltd., synthetic swelling mica (trade name: Somasif ME-100, average particle size: 1-3 ⁇ m, manufactured by Coop Chemical Co.), synthetic smectite (product name: Lucentite SWN, average particle size: 0.02 ⁇ m, manufactured by Corp Chemical Co.) and synthetic smectite (trade name: Lucentite SWF, average particle size: 0.02 ⁇ m, manufactured by Corp Chemical Co.) are preferably used.
- natural montmorillonite trade name: Kunipia F, average particle size: 0.1 to 1 ⁇ m, manufactured by Kunimine Kogyo Co., Ltd.
- an organic layered clay mineral can be used as the layered clay mineral (B).
- Organized layered clay mineral can be obtained by performing cation exchange between common layers, for example, by adding organic onium ions to the aqueous slurry of layered clay mineral described above, and stirring and reacting. be able to.
- the organic onium ion is a compound containing an element having a lone pair such as oxygen, sulfur, nitrogen, etc., and a proton or other cationic reagent is coordinated to these lone pairs. Is an ion generated from the organic onium compound generated.
- the conditions for organicizing with organic onium ions are not particularly limited, but it is preferable to react the organic onium ions in an amount of 0.3 to 2.0 times the cation exchange capacity of the layered clay mineral.
- the reaction is more preferably performed in an amount of 0.5 to 1.5 times, and the reaction is preferably performed at a temperature of 10 to 95 ° C.
- organic onium ions examples include ammonium ions, phosphonium ions, oxonium ions, sulfonium ions, and the like.
- ammonium ions are the most common, and specifically include aliphatic ammonium ions, pyridinium ions, quinolinium ions, imidazolium ions, pyrrolidinium ions, piperidinium ions, betaines, lecithin, and cationic dyes. (Pigment) etc. are mentioned.
- an aliphatic ammonium ion represented by the following formula (I) or (II) is preferable, and specifically, for example, hydroxypolyoxyethylene trialkylammonium, hydroxypolyoxypropylene trialkylammonium, di (hydroxypolyoxyethylene) Dialkylammonium, di (hydroxypolyoxypropylene) dialkylammonium, dimethyldioctylammonium, dimethyldidodecylammonium, methylethyldioctylammonium, methylethyldioctylammonium, methyltrioctylammonium, methyltridodecylammonium, benzylmethyldioctylammonium, benzylmethyldi Dodecyl ammonium, benzyl ethyl dioctyl ammonium, benzyl ethyl dioctyl ammonium Um, benzyl
- R 1 represents a hydrocarbon group having 1 to 30 carbon atoms
- R 2 and R 3 are each independently a polyoxyethylene group (— (CH 2 CH 2 O) n —H)
- polyoxy represents a propylene group (— (CH 2 CH (CH 3 ) O) n —H, — (CH 2 CH 2 CH 2 O) n —H) or a hydrocarbon group having 1 to 10 carbon atoms
- R 4 represents polyoxy Ethylene group (— (CH 2 CH 2 O) n —H) or polyoxypropylene group (— (CH 2 CH (CH 3 ) O) n —H, — (CH 2 CH 2 CH 2 O) n —H) Represents.
- n 1 to 50 is represented.
- R 1 represents a methyl group or a benzyl group
- R 2 represents a hydrocarbon group having 1 to 3 carbon atoms or a hydrocarbon group having 6 to 15 carbon atoms
- R 3 and R 4 are each independently Represents a hydrocarbon group having 6 to 15 carbon atoms.
- an organized layered clay mineral commercially available products can be used, and specifically, for example, Esbene NX, Esbene WX, Organite, Organite D manufactured by Hojun Co., Ltd. Tight SEN, Lucentite SPN, Lucentite SAN, Lucentite STN, Somasif MAE, Somasif MEE, Somasif MPE, Somasif MTE, etc. can be used.
- the layered clay mineral (B) preferably has an alkylsilyl group because the moisture resistance of the photoelectric conversion element of the present invention becomes better.
- the layered clay mineral (B) having an alkylsilyl group for example, the layered clay mineral exemplified above (hereinafter also referred to as “layered clay mineral (b1)”) and an organosilane compound (b2) described later are reacted. What was made to use, the commercial item mentioned later, etc. can be used.
- Organosilane compound (b2) As the organosilane compound (b2) used for the preparation of the layered clay mineral (B), for example, a compound represented by the following formula (III) can be used.
- R 8 represents a monovalent hydrocarbon group having 1 to 25 carbon atoms which may be branched, and may contain a hetero atom.
- R 9 represents a hydrolyzable group, and n represents an integer of 1 to 3.
- a plurality of R 8 s when n is 2 or 3 may be the same or different, and a plurality of R 9 s when n is 1 or 2 may be the same or different.
- the monovalent hydrocarbon group optionally having 1 to 25 carbon atoms represented by R 8 is, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1,2-dimethylpropyl Group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, hexadecyl group, octadecyl group, cyclohexyl group, vinyl group, allyl group, phenyl group, tolyl group, styryl group, ⁇
- Specific examples of the compound represented by the above formula (III) include, for example, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, and n-propyl.
- organosilane compound (b2) a condensate of the compound represented by the above formula (III) can be used, and specific examples thereof include dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane. And organopolysiloxanes such as siloxane. Furthermore, as the organosilane compound (b2), organodisilazane such as hexamethyldisilazane and divinyltetramethyldisilazane can be used.
- the reaction between the layered clay mineral (b1) and the organosilane compound (b2) is not particularly limited.
- they are stirred in an organic solvent such as methanol at a temperature of about 0 to 250 ° C.
- the hydroxyl group of the layered clay mineral (b1) reacts with the hydrolyzable group of the organosilane compound (b2), whereby the layered clay mineral (B) having an alkylsilyl group can be prepared.
- the hydroxyl group possessed by the layered clay mineral (b1) refers to a hydroxyl group usually possessed by a crystal layer (mainly an end face) of a known layered clay mineral such as montmorillonite or smectite.
- a commercially available product can be used as the layered clay mineral (B) having an alkylsilyl group.
- a silane-treated montmorillonite treated with an alkyltrialkoxysilane Benger SH, manufactured by Hojun Co., Ltd.
- 4 Silane-treated organic bentonite manufactured by Hojun Co.
- quaternary ammonium and alkyltrialkoxysilane is preferably used.
- a photoelectric conversion element having superior moisture resistance By containing such a layered clay mineral (B) having an alkylsilyl group, a photoelectric conversion element having superior moisture resistance can be formed.
- the layered clay mineral (B) having an alkylsilyl group is made more hydrophobic than the conventionally known layered clay mineral, thereby preventing intrusion of water vapor in the atmosphere. This is probably because of this.
- the content of the layered clay mineral (B) is preferably 0.1 to 250 parts by mass in terms of inorganic matter, with respect to 100 parts by mass of the organic solvent (A), preferably 0.5 to More preferably, it is 150 parts by mass.
- the inorganic substance conversion is based on the content of the clay mineral on the organic layer, and when the clay mineral on the organic layer is used, the cation between layers, that is, the mass excluding the above-mentioned organic onium ion is excluded.
- the layered clay mineral which is not organized is an inorganic substance including cations between layers (for example, Na + , K + , Li +, etc.), the inorganic substance conversion and the total amount conversion have the same value.
- Organic salt compound (C) optionally contained in the electrolyte of the present invention is an organic salt compound having a tertiary or quaternary cation and an anion which is a counter ion thereof, and is solid and liquid (so-called ionic liquid) at room temperature. ).
- the tertiary cation refers to a cation in which a positively charged periodic table group 16 element (for example, an oxygen atom, a sulfur atom, etc.) does not have a hydrogen atom
- the quaternary cation is A cation in which a Group 15 element (for example, a nitrogen atom or a phosphorus atom) having a positive charge does not have a hydrogen atom.
- R 1 represents a hydrocarbon group that may contain a heteroatom having 1 to 20 carbon atoms, and has a substituent that may contain a heteroatom having 1 to 20 carbon atoms. May be.
- R 2 and R 3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and may contain a hetero atom. However, when the nitrogen atom contains a double bond, R 3 does not exist.
- Q represents a nitrogen atom, an oxygen atom, a phosphorus atom or a sulfur atom
- R 4 , R 5 , R 6 and R 7 are each independently a hydrogen atom or a hydrocarbon having 1 to 8 carbon atoms. Represents a group and may contain a heteroatom. However, when Q is an oxygen atom or a sulfur atom, R 7 does not exist, and when Q is a sulfur atom, R 4 and R 5 may be linked.
- the hydrocarbon group which may contain a hetero atom having 1 to 20 carbon atoms of R 1 in the above formula (1) includes a ring structure together with a nitrogen atom (ammonium ion) in the above formula (1). It is preferable to take it.
- the substituent which may have a hetero atom having 1 to 20 carbon atoms which R 1 in the above formula (1) may have is an alkyl group having 1 to 20 carbon atoms (for example, methyl Group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, ethylhexyl group, nonyl group, decyl group, dodecyl group, undecyl group, hexadecyl group, octadecyl group, cyclopropylmethyl group, tripropyl group Fluoroethyl group, etc.), alkenyl group having 2 to 20 carbon atoms (for example, vinyl group, allyl group, etc.), aryl group having 6 to 20 carbon atoms (for example, phenyl group, tolyl group, naphthyl group, etc.), carbon number 7 -20 aralkyl
- an alkyl group having 1 to 20 carbon atoms for example, , Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, ethylhexyl group, nonyl group, decyl group, dodecyl group, undecyl group, hexadecyl group, octadecyl group, cyclopropylmethyl group , Trifluoroethyl group, etc.), C 2-20 alkenyl group (eg, vinyl group, allyl group, etc.), C 6-20 aryl group (eg, phenyl group, tolyl group, naphthyl group, etc.), carbon 7 to 20 aralkyl groups (for example, Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group,
- the hydrocarbon group which may contain a hetero atom having 1 to 8 carbon atoms of R 4 , R 5 , R 6 and R 7 is specifically 1 to 1 carbon atom.
- 8 alkyl groups for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc.
- alkoxy groups having 1 to 8 carbon atoms for example, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, tert-butoxy group, sec-butoxy group, n-pentoxy group, n-hexoxy group, 1,2-dimethylbutoxy group, etc.
- C 2-8 Alkyl alkoxy groups for example, methylene methoxy group (—CH 2 OCH 3 ), ethylene methoxy group (—CH 2 CH 2 OCH 3 ), n-propylene-is
- Examples of the cation represented by the above formula (1) include imidazolium ion, pyridinium ion, pyrrolidinium ion, piperidinium ion, and the like.
- a cation represented by any of the following formulas (3) to (6) is preferably exemplified.
- a cation represented by the following formulas (3) and (5) is preferable because the photoelectric conversion efficiency of the photoelectric conversion element of the present invention tends to be better.
- R each independently represents a hydrocarbon group that may contain a heteroatom having 1 to 20 carbon atoms. More specifically, the following cations are mentioned.
- Examples of the cation represented by the above formula (2) include organic cations such as ammonium ion, sulfonium ion, phosphonium ion, and oxonium ion. Specifically, the following cations are preferably exemplified. Among these, aliphatic quaternary ammonium ions and sulfonium ions (particularly thiophenium ions) are preferable because the photoelectric conversion efficiency of the photoelectric conversion element of the present invention tends to be better.
- anions of the organic salt compound (C) include I ⁇ , Br ⁇ , AlCl 4 ⁇ , Al 2 Cl 7 ⁇ , NO 3 ⁇ , BF 4 ⁇ , PF 6 ⁇ and CH 3.
- bromine ions (Br ⁇ ) and iodine ions (I ⁇ ) are preferable because the photoelectric conversion efficiency of the photoelectric conversion element of the present invention tends to be better, and iodine ions (I ⁇ ). More preferably.
- a thiocyanate anion (SCN ⁇ ) is preferable because the heat resistance of the photoelectric conversion element of the present invention is improved.
- the metal complex is heated by heating. Even if the coordination of the thiocyanate anion is off, the thiocyanate anion of the organic salt compound (C) can be re-coordinated, and functions as a dye, that is, a function of absorbing light and releasing electrons. It is thought that it was possible to maintain.
- a metal complex coordinated with a thiocyanate anion for example, a ruthenium complex dye described later
- organic salt compound (C) the organic salt compound etc. which consist of a combination of the cation and anion which were illustrated above are mentioned, for example.
- an organic salt compound having an imidazolium ion as a cation and an iodine ion as an anion is preferable because the photoelectric conversion efficiency of the photoelectric conversion element of the present invention becomes better, and the heat resistance of the photoelectric conversion element of the present invention is preferred.
- the organic salt compound having a thiocyanate anion is preferable, and the organic salt compound having an imidazolium ion and an iodine ion and the organic salt compound having a thiocyanate anion are more preferably used in combination.
- the method for synthesizing the organic salt compound (C) is not particularly limited, and various organic salt compounds composed of combinations of cations and anions exemplified above can be synthesized by a conventionally known method.
- Examples of the organic salt compound (C) include 1-methyl-3-methylimidazolium iodide, 1-ethyl-3-methylimidazolium iodide, 1-methyl-3-pentylimidazolium iodide, 1-methyl- 3-hexylimidazolium iodide, 1-((2-methoxyethoxy) ethyl) -3-((2-methoxyethoxy) ethyl) imidazolium iodide, 1-methyl-1-butylpyrrolidinium thiocyanate, 1- In addition to synthetic products such as methyl-1-ethylpyrrolidinium thiocyanate, commercially available products can be used.
- 1-methyl-3-propylimidazolium iodide manufactured by Tokyo Chemical Industry Co., Ltd.
- 1-methyl-3-butylimidazolium iodide manufactured by Tokyo Chemical Industry Co., Ltd.
- 1-methyl-1-methyl -Pyrrolidinium iodide Aldrich
- tetrapropylammonium iodide Tokyo Kasei
- tetrabutylammonium iodide Tokyo Chemical
- 1-ethyl-3-methylimidazolium tetracyanoborate Merck
- 1) -ethyl-3-methylimidazolium thiocyanate Merck
- 1-methyl-3-butylimidazolium thiocyanate BASF
- tetrapropylammonium thiocyanate Merck
- 1-ethyl- 3-methylimidazolium bis trifluoromethylsulfony
- the organic salt compound (C) in the present invention includes the tautomer.
- “1-methyl-3-pentylimidazolium iodide” includes “1-pentyl-3-methylimidazolium iodide” which is a tautomer thereof, and includes “1-methyl- “3-Hexylimidazolium iodide” is intended to include “1-hexyl-3-methylimidazolium iodide” which is a tautomer thereof.
- the content when the organic salt compound (C) is contained, the content is preferably 5 to 70 parts by mass with respect to 100 parts by mass of the organic solvent (A), and 10 to 60 parts by mass. It is more preferable that Moreover, when it contains the said organic salt compound (C), the ratio (A / C) of the said organic solvent (A) and the said organic salt compound (C) shows the outstanding moisture resistance of the photoelectric conversion element of this invention. From the viewpoint of holding and suppressing elution of the photosensitizing dye (especially organic dye) in the dye-sensitized solar cell of the present invention, it is preferably 59/41 to 95/5, and 63/37 to 90 / 10 is more preferable.
- the electrolyte of the present invention can be added with a redox pair (redox pair).
- redox pair any one generally used or usable in a dye-sensitized solar cell can be used as long as the object of the present invention is not impaired.
- iodine / iodide ions, bromine / bromide ions, and the like can be used.
- metal iodides of iodine and LiI, NaI, KI, etc. iodide salts of iodine and quaternary imidazolium compounds, iodide salts of iodine and quaternary pyridinium compounds, iodine and tetraalkylammonium compounds
- Iodide / iodide ion pairs such as iodide salts with; bromide and metal bromides with LiBr, NaBr, KBr, etc., bromide salts with bromine and quaternary imidazolium compounds, bromide salts with bromine and quaternary pyridinium compounds, Bromine / bromide ions such as bromide salts of bromine and tetraalkylammonium compounds; metal complexes such as ferrocyanate-ferricyanate, ferrocene-ferricinium salts, cobalt complexes; sulfur compounds
- the electrolyte of this invention can add inorganic salt and / or organic salt from a viewpoint of improving the short circuit current of the photoelectric conversion element of this invention.
- inorganic salts and organic salts include alkali metal, alkaline earth metal salts, and the like.
- lithium iodide sodium iodide, potassium iodide, magnesium iodide, calcium iodide
- examples include lithium trifluoroacetate, sodium trifluoroacetate, lithium thiocyanate, lithium tetrafluoroborate, lithium hexafluorophosphate, lithium perchlorate, lithium trifluoromethanesulfonate, and lithium bis (trifluoromethanesulfonyl) imide. These may be used alone or in combination of two or more.
- the amount of the inorganic salt or organic salt added is not particularly limited, and can be the same as before as long as the object of the present invention is not impaired.
- pyridines and benzimidazoles can be added to the electrolyte of this invention from a viewpoint of improving the open circuit voltage of the photoelectric conversion element of this invention.
- alkyl pyridines such as methyl pyridine, ethyl pyridine, propyl pyridine and butyl pyridine
- alkyl imidazoles such as methyl imidazole, ethyl imidazole and propyl imidazole
- alkylbenzimidazoles such as imidazole, and the like. These may be used alone or in combination of two or more.
- the addition amount of pyridines and benzimidazoles is not particularly limited, and can be conventional as long as the object of the present invention is not impaired.
- the electrolyte of the present invention may contain an organic solvent other than the organic solvent (A).
- organic solvent other than the organic solvent (A).
- Specific examples thereof include carbonates such as ethylene carbonate and propylene carbonate; ethylene glycol dialkyl ether, propylene glycol dialkyl ether and the like.
- Ethers such as ethylene glycol monoalkyl ether and propylene glycol monoalkyl ether; polyhydric alcohols such as ethylene glycol and propylene glycol; acetonitrile, propionitrile, methoxypropionitrile, cyanoethyl ether, glutaronitrile, Nitriles such as valeronitrile; Lactones such as ⁇ -butyrolactone; Amides such as dimethylformamide and N-methylpyrrolidone; Non-prote such as dimethylsulfoxide and sulfolane Emissions polar solvents; and the like, may be used those either alone, or in combination of two or more.
- the content of the organic solvent is not particularly limited, and can be conventional as long as the object of the present invention is not impaired.
- the method for producing the electrolyte of the present invention is not particularly limited.
- the organic solvent (A) and the layered clay mineral (B) described above and the organic salt compound (C) which may be optionally contained are mixed, a ball mill, Thoroughly mix evenly at room temperature or under heating (eg 40 to 150 ° C) using a sand mill, pigment disperser, pulverizer, ultrasonic disperser, homogenizer, planetary mixer, Hobart mixer, roll, kneader, etc. It can be produced by dispersing (kneading).
- an organic solvent for example, toluene or the like
- the organic solvent may be distilled off after mixing.
- FIG. 1 is a schematic cross-sectional view showing an example of the basic configuration of the photoelectric conversion element of the present invention.
- the photoelectric conversion element of the present invention includes a photoelectrode having a transparent conductive film and a metal oxide semiconductor porous film, a counter electrode disposed to face the photoelectrode, and the photoelectrode and the counter electrode. It is a photoelectric conversion element which has an electrolyte layer arranged.
- the photoelectrode includes a transparent substrate 1, a transparent conductive film 2, and an oxide semiconductor porous film 3.
- the transparent substrate 1 preferably has good light transmittance.
- Specific examples thereof include a glass substrate, polystyrene, polyethylene, polypropylene, polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyphenylene sulfide, and cyclic olefin polymer.
- resin substrates (films) such as polyethersulfone, polysulfone, polyetherimide, polyarylate, triacetylcellulose, and polymethylmethacrylate.
- the transparent conductive film 2 specifically, for example, conductive metal oxides such as tin oxide doped with antimony or fluorine, zinc oxide doped with aluminum or gallium, indium oxide doped with tin, etc. Is mentioned.
- the thickness of the transparent conductive film 2 is preferably about 0.01 to 1.0 ⁇ m.
- the method for providing the transparent conductive film 2 is not particularly limited, and examples thereof include a coating method, a sputtering method, a vacuum deposition method, a spray pyrolysis method, a chemical vapor deposition method (CVD), and a sol-gel method.
- the oxide semiconductor porous film 3 is obtained by applying a dispersion of oxide semiconductor fine particles on the transparent conductive film 2.
- oxide semiconductor fine particles include titanium oxide, tin oxide, zinc oxide, tungsten oxide, zirconium oxide, hafnium oxide, strontium oxide, vanadium oxide, niobium oxide, and the like. You may use independently and may use 2 or more types together.
- the dispersion is obtained by mixing the oxide semiconductor fine particles and the dispersion medium with a dispersing machine such as a sand mill, a bead mill, a ball mill, a three roll mill, a colloid mill, an ultrasonic homogenizer, a Henschel mixer, or a jet mill.
- the dispersion is preferably obtained by mixing with a disperser and then subjected to ultrasonic treatment using an ultrasonic homogenizer or the like immediately before use (coating). By performing ultrasonic treatment immediately before use, the photoelectric conversion efficiency of the photoelectric conversion element of the present invention becomes better.
- the oxide semiconductor porous film formed using a dispersion liquid subjected to ultrasonic treatment immediately before use is easily filled with the electrolyte of the present invention or the adsorption ability of the dye is increased.
- acetylacetone, hydrochloric acid, nitric acid, a surfactant, a chelating agent, or the like may be added to the dispersion. Therefore, a polymer such as polyethylene oxide and polyvinyl alcohol, a cellulose-based thickener, or the like may be added.
- dispersion examples include titanium oxide pastes SP100 and SP200 (both manufactured by Showa Denko KK), titanium oxide fine particles Ti-Nanoxide® T (manufactured by Solaronics), Ti-Nanoxide® D (manufactured by Solaronics), Ti-Nanoxide®T / SP (manufactured by Solaronics), Ti-Nanoxide® D / SP (manufactured by Solaronics), titania coating paste PECC01 (manufactured by Pexel Technologies), titania particle paste PST-18NR, PST-400C It is also possible to use commercially available products such as those manufactured by the same company.
- a known wet film forming method can be used as a method for applying the dispersion on the transparent conductive film.
- a known wet film forming method can be used.
- Specific examples of the wet film forming method include a screen printing method, an ink jet printing method, a roll coating method, a doctor blade method, a spin coating method, and a spray coating method.
- heat treatment for the purpose of improving electronic contact between the fine particles, improving adhesion with the transparent conductive film, and improving film strength, heat treatment, chemical treatment, plasma, It is preferable to perform ozone treatment or the like.
- the temperature of the heat treatment is preferably 40 ° C. to 700 ° C., and preferably 40 ° C. to 650 ° C.
- the heat treatment time is not particularly limited, but is usually about 10 seconds to 24 hours.
- Specific examples of the chemical treatment include chemical plating treatment using a titanium tetrachloride aqueous solution, chemical adsorption treatment using a carboxylic acid derivative, and electrochemical plating treatment using a titanium trichloride aqueous solution.
- the counter electrode is an electrode 5 disposed to face the photoelectrode 4.
- a metal substrate a glass substrate having a conductive film on the surface, a resin substrate, or the like can be used.
- metal substrate metals such as platinum, gold, silver, copper, aluminum, indium, and titanium can be used.
- resin substrate in addition to the substrate (film) exemplified as the transparent substrate 1 constituting the photoelectrode 4, a general resin substrate which is opaque or inferior in transparency can also be used.
- metals such as platinum, gold, silver, copper, aluminum, indium and titanium; carbon; tin oxide; tin oxide doped with antimony and fluorine; zinc oxide; doped with aluminum and gallium Zinc oxide; indium oxide doped with tin; conductive metal oxides such as;
- the thickness and formation method of the conductive film can be the same as those of the transparent conductive film 2 constituting the photoelectrode 4.
- the counter electrode 5 may be an electrode in which a conductive polymer film is formed on a substrate or a conductive polymer film electrode.
- the conductive polymer include polythiophene, polypyrrole, polyaniline, and the like.
- a method for forming a conductive polymer film on a substrate a conductive polymer film is formed on a substrate from a polymer dispersion using a dipping method, a spin coating method, or the like that is usually known as a wet film formation method. be able to.
- Examples of the conductive polymer dispersion include the polyaniline dispersion disclosed in JP-A-2006-169291, a commercially available polythiophene derivative aqueous dispersion (Vitron P, manufactured by Bayer), Mitsubishi Rayon Co., Ltd. (Aqua Save, polyaniline). Derivative aqueous solution) and the like can be used.
- a conductive polymer film can be formed on the substrate by an electrolytic polymerization method in addition to the above method.
- Conductive polymer film electrode is a casting that is usually known as a wet film-forming method from a self-supporting film or a conductive polymer dispersion obtained by peeling off a conductive polymer film formed on an electrode by electrolytic polymerization. It is also possible to use a self-supporting film formed using a method or a spin coating method.
- the conductive polymer dispersion referred to here is a conductive polymer dispersion in which conductive polymer fine particles are dispersed in a solvent and a conductive polymer is dissolved in a solvent. A functional polymer dispersion.
- the electrolyte layer is an electrolyte layer 6 provided between the photoelectrode 4 and the counter electrode 5, and the above-described electrolyte of the present invention is used in the photoelectric conversion element of the present invention.
- the photoelectric conversion element of the present invention uses the above-described electrolyte of the present invention, excellent moisture resistance can be achieved.
- the dye-sensitized solar cell of the present invention is one type of photoelectric conversion element in which a photosensitizing dye is supported on the photoelectrode that constitutes the above-described photoelectric conversion element of the present invention.
- the photosensitizing dye is not particularly limited as long as it is a dye having absorption in the visible light region and / or the infrared light region, and a metal complex, an organic dye, or the like can be used.
- the metal complex examples include a ruthenium complex dye (see the following formula) coordinated with a ligand such as a bipyridine structure or a terpyridine structure, an iron complex dye, an osmium complex dye, a platinum complex dye, or an iridium complex.
- a dye, metal phthalocyanine, metal porphyrin, or the like can be used.
- organic dye specifically, for example, porphyrin dye, phthalocyanine dye, cyanine dye, merocyanine dye, xanthene dye, coumarin dye, indole dye, fluorene dye, triphenylamine System dyes can be used.
- the method for supporting the photosensitizing dye is not particularly limited.
- the dye is dissolved in water, an alcohol solvent, a nitrile solvent, and the oxide semiconductor porous film 3 is immersed in the dye solution or the dye solution. Is supported on the oxide semiconductor porous film 3 by coating.
- the produced photoelectrode was converted into a ruthenium complex dye (cis- (diisothiocyanate) -N, N′-bis (2,2′-bipyridyl-4,4′-dicarboxyl acid) ruthenium (II) complex) (Ruthenium). It was immersed in a butyl alcohol / acetonitrile solution (volume ratio: 1/1, concentration 3 ⁇ 10 ⁇ 4 mol / L) of 535-bisTBA (manufactured by Solaronix) for 4 hours.
- a dye-sensitized solar cell (photosensitizing dye: photosensitizing dye :) is prepared by interposing a heat-sealing film between the photoelectrode and the platinum counter electrode and heat-sealing at 150 ° C.
- a ruthenium complex dye 1) was obtained.
- a dye-sensitized solar cell (photosensitized) was prepared in the same manner as the dye-sensitized solar cell (photosensitized dye: ruthenium complex dye) except that an indoline dye (D149, manufactured by Mitsubishi Paper Industries) was used instead of the ruthenium complex dye.
- Sensitive dye: organic dye was prepared.
- the obtained two types of dye-sensitized solar cells were measured and evaluated for photoelectric conversion efficiency, heat resistance, moisture resistance, and moist heat resistance by the following methods. The results are shown in Table 1 and the like.
- ⁇ Photoelectric conversion efficiency> As shown in FIG. 2, a solar simulator is used as a light source, and AM1.5 simulated sunlight is irradiated from the photoelectrode side with a light intensity of 100 mW / cm 2 , and a current-voltage measuring device (Digital Source Meter 2400 manufactured by Keithley Instruments Co., Ltd.). ) To determine the conversion efficiency.
- ⁇ Moisture resistance (maintenance rate)> The dye-sensitized solar cell whose photoelectric conversion efficiency was measured was allowed to stand for 1000 hours under conditions of 40 ° C. and 85% RH, and thereafter the photoelectric conversion efficiency was measured by the same method as described above, and the maintenance rate (photoelectricity after humidification) Conversion efficiency / photoelectric conversion efficiency before humidification) was calculated. As a result, if the maintenance ratio of photoelectric conversion efficiency is 0.80 or more, it can be evaluated that the moisture resistance is excellent.
- Organic solvent A1 methoxypropionitrile (boiling point: 166 ° C., relative dielectric constant: 25)
- Organic solvent A2 butoxypropionitrile (boiling point: 206 ° C., relative dielectric constant: 20)
- Organic solvent A3 propylene carbonate (boiling point: 240 ° C., relative dielectric constant: 65)
- Organic solvent A4 ethyl isopropyl sulfone (boiling point: 250 ° C., relative dielectric constant: 32)
- Organic solvent X acetonitrile (boiling point: 82 ° C., relative dielectric constant: 21)
- Organic solvent Y quinoline (boiling point: 237 ° C., relative dielectric constant: 9)
- Layered clay mineral B1 Synthetic smectite (trade name: Lucentite SPN (Organized layered clay mineral obtained by organizing Lucentite S)
- the electrolytes of Comparative Examples 1, 7, 11 and 17 prepared without containing the layered clay mineral (B) have a photoelectric conversion efficiency after heating and after humidification. It was found that the maintenance rate was small and the heat resistance, moisture resistance, and heat and humidity resistance were poor.
- the electrolytes of Comparative Examples 2 to 6, 8 to 10, 12 to 16, and 18 to 20 prepared without containing the organic solvent (A) have a small maintenance rate of photoelectric conversion efficiency after heating and after humidification, It turned out that it is inferior to heat resistance, moisture resistance, and heat-and-moisture resistance.
- the electrolytes of Examples 1 to 41 prepared using the organic solvent (A) and the layered clay mineral (B) all have a high retention rate of photoelectric conversion efficiency after humidification and excellent moisture resistance. I understood. Moreover, it turned out that the electrolyte prepared using the layered clay mineral B2 which has an alkylsilyl group as a layered clay mineral (B) tends to be further excellent in moisture resistance. Further, for the dye-sensitized solar cell using the ruthenium complex dye 1 or 2 as the photosensitizing dye, the organic salt compounds C4 and C5 having a thiocyanate anion as the organic chloride compound (C) were blended.
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Abstract
Description
しかしながら、色素増感太陽電池は、電気化学電池のため電解質として有機電解液やイオン性液体等が使用されており、有機電解液を用いる場合には、長期使用時に揮発したり枯渇したりすることにより発電効率が低下してしまうという問題があり、また、イオン性液体を用いる場合には、長期使用時の揮発や枯渇は防止できるものの液漏れすることによる構造劣化等の耐久性の問題があった。
そこで、電解液の揮発、液漏れを防ぎ、太陽電池の長期安定性、耐久性確保を目的として、電解質を液状からゲル状、固体状にする研究が行われている。
これは、光電変換素子内に侵入した水分や湿気が、電解質や増感色素を変質させるためであると考えられる。
即ち、本発明は、下記(a)~(g)を提供する。
上記有機溶媒(A)の沸点が150℃以上であり、比誘電率が20以上である光電変換素子用電解質。
上記光電極に対向して配置される対向電極と、
上記光電極と上記対向電極との間に配された電解質層とを有し、
上記電解質層が、上記(a)~(e)のいずれかに記載の光電変換素子用電解質である光電変換素子。
また、本発明の色素増感太陽電池は、耐湿性に優れるため、例えば、湿度が大きく変動する外気に暴露される使用環境下においても適用することができ、非常に有用である。
本発明の光電変換素子用電解質(以下、単に「本発明の電解質」ともいう。)は、有機溶媒(A)および層状粘土鉱物(B)を含有する光電変換素子用電解質であって、上記有機溶媒(A)の沸点が150℃以上であり、比誘電率が20以上である光電変換素子用の電解質である。
また、本発明の電解質は、揮発を抑制し、光電極の安定性を高める観点から、第3級または第4級カチオンを有する有機塩化合物(C)を含有するのが好ましい。
次に、本発明の電解質の各成分について詳述する。
本発明の電解質に用いる有機溶媒(A)は、沸点が150℃以上であり、比誘電率が20以上である有機溶媒であれば特に限定されない。
ここで、沸点とは、1気圧における沸点をいい、比誘電率とは、25℃および10kHzを印加させる液体用誘電率計(液体誘電率計M-870、日本ルフト社製)を用いて測定した値をいう。
これらのうち、本発明の電解質を用いた光電変換素子(以下、「本発明の光電変換素子」ともいう。)の光電変換効率がより良好となる理由から、メトキシプロピオニトリル、エトキシプロピオニトリル、ブトキシプロピオニトリルを用いるのが好ましく、入手が容易でコストが安い理由から、プロピレンカーボネート、ジエチルカーボネート、エチルメチルカーボネート、γ-ブチロラクトンが好ましく、電気化学的に安定であり、分解ガスの発生が少ない理由から、エチルイソプロピルスルホン、スルホラン、メチルスルホランが好ましい。
これは、詳細には明らかではないが、有機溶媒(A)がイオン性液体よりも吸湿性が低く、また、長期使用時においても揮発が少なく、かつ、他の電解質の成分に対する溶解性も高いためと考えられる。また、有機溶媒(A)中で後述する層状粘土鉱物(B)が分散していることにより、大気中の水蒸気の侵入を抑制することができ、更に、本発明の光電変換素子の電解質層に侵入した水分が、層状粘土鉱物(B)の層間にトラップされ、電解質層や光電極に担持させる光増感色素の変性、脱離等が抑制されるためと考えられる。
本発明の電解質に用いる層状粘土鉱物(B)は特に限定されないが、ケイ酸四面体が2次元シート状に結合したフィロケイ酸塩であるのが好ましく、その具体例としては、モンモリロナイト、ベントナイト、サポナイト、バイデライト、ノントロナイト、ヘクトライト、スティブンサイトなどのスメクタイト系粘土鉱物;バーミキュライトなどのバーミキュライト系粘土鉱物;ムスコバイト、フロコバイト、マイカなどの雲母系粘土鉱物;等が挙げられ、これらを1種単独で用いてもよく、2種以上を併用してもよい。
また、本発明の電解質に用いる層状粘土鉱物(B)は、天然物であっても、合成品であってもよい。
ここで、層状粘土鉱物の陽イオン交換容量は、10~300ミリ当量/100gであるのが好ましい。
有機化層状粘土鉱物は、一般的な層間の陽イオン交換を行なうことで得ることができ、例えば、上述した層状粘土鉱物の水系スラリーに有機オニウムイオンを添加し、撹拌させて反応させることにより得ることができる。
ここで、有機オニウムイオンとは、酸素、硫黄、窒素等のような孤立電子対を有する元素を含む化合物において、これらの孤立電子対にプロトンまたは他の陽イオン型の試薬等が配位結合して生じた有機オニウム化合物から発生したイオンである。
また、有機オニウムイオンで有機化するための条件は特に限定されないが、層状粘土鉱物の陽イオン交換容量に対して、有機オニウムイオンを0.3~2.0倍量で反応させるのが好ましく、0.5~1.5倍量で反応させるのがより好ましく、また、10~95℃の温度で反応させるのが好ましい。
これらのうち、アンモニウムイオンが最も一般的であり、具体的には、脂肪族アンモニウムイオン、ピリジニウムイオン、キノリニウムイオン、イミダゾリウムイオン、ピロリジニウムイオン、ピペリジニウムイオン、ベタイン類、レシチン、カチオン染料(色素)等が挙げられる。
また、下記式(I)または(II)に示す脂肪族アンモニウムイオンが好ましく、具体的には、例えば、ヒドロキシポリオキシエチレントリアルキルアンモニウム、ヒドロキシポリオキシプロピレントリアルキルアンモニウム、ジ(ヒドロキシポリオキシエチレン)ジアルキルアンモニウム、ジ(ヒドロキシポリオキシプロピレン)ジアルキルアンモニウム、ジメチルジオクチルアンモニウム、ジメチルジドデシルアンモニウム、メチルエチルジオクチルアンモニウム、メチルエチルジオクチルアンモニウム、メチルトリオクチルアンモニウム、メチルトリドデシルアンモニウム、ベンジルメチルジオクチルアンモニウム、ベンジルメチルジドデシルアンモニウム、ベンジルエチルジオクチルアンモニウム、ベンジルエチルジオクチルアンモニウム、ベンジルトリオクチルアンモニウム、ベンジルトリドデシルアンモニウム等が挙げられる。
アルキルシリル基を有する層状粘土鉱物(B)としては、例えば、上記で例示した層状粘土鉱物(以下、「層状粘土鉱物(b1)」ともいう。)と後述するオルガノシラン化合物(b2)とを反応させたものや、後述する市販品等を用いることができる。
上記層状粘土鉱物(B)の調製に用いるオルガノシラン化合物(b2)としては、例えば、下記式(III)で表される化合物等を用いることができる。
また、上記式(III)中、R9の加水分解性基としては、具体的には、例えば、アルコキシ基、アシル基、ハロゲン基等が挙げられる。
更に、上記オルガノシラン化合物(b2)としては、ヘキサメチルジシラザン、ジビニルテトラメチルジシラザン等のオルガノジシラザンを用いることができる。
ここで、層状粘土鉱物(b1)が有する水酸基とは、モンモリロナイトやスメクタイト等の公知の層状粘土鉱物の結晶層(主に端面)が通常有している水酸基をいうが、上記反応においては、層状粘土鉱物(b1)が有する全ての水酸基がアルキルシリル基で置換されている必要はない。
なお、上記反応においては、層状粘土鉱物(b1)とオルガノシラン化合物(b2)との反応後またはこれらの反応と同時に、オルガノシラン化合物(b2)由来の加水分解性基(層状粘土鉱物(b1)と未反応であった官能基)が加水分解し、縮合していてもよい。
これは、詳細には明らかではないが、アルキルシリル基を有する層状粘土鉱物(B)が従来公知の層状粘土鉱物よりも疎水化されていることにより、大気中の水蒸気の侵入を防ぐことができるためと考えられる。
また、無機物換算とは、有機化層上粘土鉱物の含有量を考慮したものであり、有機化層上粘土鉱物を使用する場合には層間の陽イオン、すなわち上述した有機オニウムイオンを除外した質量をいう。なお、有機化されていない層状粘土鉱物については、層間の陽イオン(例えば、Na+、K+、Li+等)も含めて無機物であるため、無機物換算と全体量換算は同じ値となる。
本発明の電解質が所望により含有する有機塩化合物(C)は、第3級または第4級カチオンならびにその対イオンであるアニオンを有する有機塩化合物であり、常温で固体および液体(いわゆるイオン性液体)のいずれであってもよい。
ここで、第3級カチオンとは、正電荷を有する周期律表第16族元素(例えば、酸素原子、硫黄原子等)が水素原子を有していないカチオンをいい、第4級カチオンとは、正電荷を有する周期律表第15族元素(例えば、窒素原子、リン原子等)が水素原子を有していないカチオンをいう。
式(2)中、Qは、窒素原子、酸素原子、リン原子または硫黄原子を表し、R4、R5、R6およびR7は、それぞれ独立に水素原子または炭素数1~8の炭化水素基を表し、ヘテロ原子を含んでいてもよい。ただし、Qが酸素原子または硫黄原子の場合、R7は存在せず、Qが硫黄原子の場合、R4およびR5は連結していてもよい。
次いで、上記式(1)中のR1が有していてもよい、炭素数1~20のヘテロ原子を含んでいてもよい置換基としては、炭素数1~20のアルキル基(例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、エチルヘキシル基、ノニル基、デシル基、ドデシル基、ウンデシル基、ヘキサデシル基、オクタデシル基、シクロプロピルメチル基、トリフルオロエチル基等)、炭素数2~20のアルケニル基(例えば、ビニル基、アリル基等)、炭素数6~20のアリール基(例えば、フェニル基、トリル基、ナフチル基等)、炭素数7~20のアラルキル基(例えば、ベンジル基、フェニルエチル基、フェニルプロピル基等)、炭素数1~20のアルコキシ基(例えば、メトキシ基、エトキシ基、n-プロポキシ基、イソ-プロポキシ基、n-ブトキシ基、tert-ブトキシ基、sec-ブトキシ基、n-ペントキシ基、n-ヘキソキシ基、1,2-ジメチルブトキシ基、ヘプトキシ基、オクトキシ基、ノニノキシ基、デシロキシ基、フェノキシ基、メチルフェノキシ基、エチルフェノキシ基等)、炭素数2~20のアルキルアルコキシ基(例えば、メチレンメトキシ基(-CH2OCH3)、エチレンメトキシ基(-CH2CH2OCH3)、n-プロピレン-イソ-プロポキシ基(-CH2CH2CH2OCH(CH3)2)、メチレン-t-ブトキシ基(-CH2-O-C(CH3)3、ブチレンメトキシ基、ペンチレンメトキシ基、へキシレンメトキシ基、ヘプチレンメトキシ基、オクチレンメトキシ基、ノニレンメトキシ基、デシレンメトキシ基、メチレンエトキシ基、エチレンエトキシ基、プロピレンエトキシ基、ブチレンエトキシ基、ペンチレンエトキシ基、へキシレンエトキシ基、エチレンエトキシメトキシ基、シクロプロピルメトキシ基、シクロヘキシルメトキシ基、メチルフェノキシ基、メトキシフェノキシ基、エトキシフェノキシ基、フェノキシフェノキシ基等)であるのが好ましい。また、上記式(1)中のR1は、この置換基を2以上有していてもよい。
具体的には、下記式(3)~(6)のいずれかで表されるカチオンが好適に例示される。
このうち、下記式(3)および(5)で表されるカチオンであるのが、本発明の光電変換素子の光電変換効率がより良好となる傾向がある理由から好ましい。
より具体的には、以下に示すカチオンが挙げられる。
具体的には、以下に示すカチオンが好適に例示される。
このうち、脂肪族4級アンモニウムイオン、スルホニウムイオン(特に、チオフェニウムイオン)であるのが、本発明の光電変換素子の光電変換効率がより良好となる傾向がある理由から好ましい。
また、本発明の光電変換素子の耐熱性が良好になるという理由から、チオシアネートアニオン(SCN-)(連結異性体であるイソチオシアネートアニオンを含む。以下同様。)が好ましい。これは、後述する実施例に示すように、チオシアネートアニオンが配位した金属錯体(例えば、後述するルテニウム錯体色素)を用いた場合に発現される効果であることを考慮すると、加熱により金属錯体からチオシアネートアニオンの配位が外れた場合であっても、有機塩化合物(C)が有するチオシアネートアニオンが再配位することが可能となり、色素としての機能、すなわち光を吸収し、電子を放出する機能を維持することができたためと考えられる。
中でも、本発明の光電変換素子の光電変換効率がより良好になるという理由から、カチオンとしてイミダゾリウムイオンを有し、アニオンとしてヨウ素イオンを有する有機塩化合物が好ましく、本発明の光電変換素子の耐熱性が良好になるという理由から、チオシアネートアニオンを有する有機塩化合物が好ましく、イミダゾリウムイオンおよびヨウ素イオンを有する有機塩化合物と、チオシアネートアニオンを有する有機塩化合物とを併用することがより好ましい。
具体的には、例えば、「1-メチル-3-ペンチルイミダゾリウムアイオダイド」は、その互変異性体である「1-ペンチル-3-メチルイミダゾリウムアイオダイド」を含み、「1-メチル-3-ヘキシルイミダゾリウムアイオダイド」は、その互変異性体である「1-ヘキシル-3-メチルイミダゾリウムアイオダイド」を含むものとする。
また、上記有機塩化合物(C)を含有する場合、上記有機溶媒(A)と上記有機塩化合物(C)との比率(A/C)は、本発明の光電変換素子の優れた耐湿性を保持し、かつ、本発明の色素増感太陽電池における光増感色素(特に有機色素)の溶出を抑制する観点から、59/41~95/5であるのが好ましく、63/37~90/10であるのがより好ましい。
本発明の電解質は、本発明の光電変換素子の光電変換効率をより向上させる観点から、酸化還元対(レドックス対)を添加することができる。
酸化還元対としては、色素増感太陽電池において一般的に使用されているまたは使用することができる任意のものを本発明の目的を損なわない範囲で用いることができる。
例えば、ヨウ素/ヨウ化物イオン、臭素/臭化物イオン等を用いることができる。具体的には、ヨウ素とLiI、NaI、KI等との金属ヨウ化物、ヨウ素と4級イミダゾリウム化合物とのヨウ化物塩、ヨウ素と4級ピリジニウム化合物とのヨウ化物塩、ヨウ素とテトラアルキルアンモニウム化合物とのヨウ化物塩等のヨウ素/ヨウ化物イオン対;臭素とLiBr、NaBr、KBr等との金属臭化物、臭素と4級イミダゾリウム化合物との臭化物塩、臭素と4級ピリジニウム化合物との臭化物塩、臭素とテトラアルキルアンモニウム化合物との臭化物塩等の臭素/臭化物イオン;フェロシアン酸塩-フェリシアン酸塩、フェロセン-フェリシニウム塩、コバルト錯体等の金属錯体;ジスルフィド化合物とメルカプト化合物との硫黄化合物;ハイドロキノン-キノン;ビオロゲン色素;等が挙げられ、これらを1種単独で用いてもよく、2種以上を併用してもよい。
これらのうち、ヨウ素/ヨウ化物イオン、臭素/臭素化物イオンが好ましい。
無機塩、有機塩としては、例えば、アルカリ金属、アルカリ土類金属塩等を挙げることができ、具体的には、ヨウ化リチウム、ヨウ化ナトリウム、ヨウ化カリウム、ヨウ化マグネシウム、ヨウ化カルシウム、トリフルオロ酢酸リチウム、トリフルオロ酢酸ナトリウム、チオシアン酸リチウム、四フッ化ホウ酸リチウム、六フッ化りん酸リチウム、過塩素酸リチウム、トリフルオロメタンスルホン酸リチウム、リチウムビス(トリフルオロメタンスルホニル)イミド等が挙げられ、これらを1種単独で用いてもよく、2種以上を併用してもよい。
無機塩、有機塩の添加量は、特に限定されず、本発明の目的を損なわない限り、従来通りとすることができる。
具体的には、メチルピリジン、エチルピリジン、プロピルピリジン、ブチルピリジン等のアルキルピリジン類;メチルイミダゾール、エチルイミダゾール、プロピルイミダゾール等のアルキルイミダゾール類;メチルベンズイミダゾール、エチルベンズイミダゾール、ブチルベンズイミダゾール、プロピルベンズイミダゾール等のアルキルベンズイミダゾール類;等が挙げられ、これらを1種単独で用いてもよく、2種以上を併用してもよい。
ピリジン類、ベンズイミダゾール類の添加量は、特に限定されず、本発明の目的を損わない限り、従来通りとすることができる。
有機溶媒の含有量は、特に限定されず、本発明の目的を損わない限り、従来通りとすることができる。
ここで、上記混合には、必要に応じて有機溶剤(例えば、トルエン等)を併用し、混合後に有機溶剤を真空留去する方法を用いてもよい。
次に、本発明の光電変換素子および色素増感太陽電池について、図1を用いて詳述する。図1は、本発明の光電変換素子の基本構成の一例を示す模式断面図である。
上記光電極は、例えば、図1に示すように、透明基板1と透明導電膜2と酸化物半導体多孔質膜3により構成されている。
ここで、透明基板1は、光透過性が良好なものが好ましく、その具体例としては、ガラス基板の他、ポリスチレン、ポリエチレン、ポリプロピレン、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリカーボネート、ポリフェニレンスルフィド、環状オレフィンポリマー、ポリエーテルサルフォン、ポリスルフォン、ポリエーテルイミド、ポリアリレート、トリアセチルセルロース、ポリメタクリル酸メチル等の樹脂基板(フィルム)が挙げられる。
また、透明導電膜2の厚さは、0.01~1.0μm程度であるのが好ましい。
更に、透明導電膜2を設けるための方法は特に限定されず、例えば、塗布法、スパッタリング法、真空蒸着法、スプレーパイロリシス法、化学気相成長法(CVD)、ゾルゲル法等が挙げられる。
上記酸化物半導体微粒子としては、具体的には、例えば、酸化チタン、酸化スズ、酸化亜鉛、酸化タングステン、酸化ジルコニウム、酸化ハフニウム、酸化ストロンチウム、酸化バナジウム、酸化ニオブ等が挙げられ、これらを1種単独で用いてもよく、2種以上を併用してもよい。
また、上記分散液は、分散機で混合して得た後、使用(塗布)直前に、超音波ホモジナイザー等を用いて超音波処理を施すのが好ましい。使用直前に超音波処理を施すことにより、本発明の光電変換素子の光電変換効率がより良好となる。これは、使用直前に超音波処理を施した分散液を用いて形成した酸化物半導体多孔質膜に対して本発明の電解質が充填されやすくなったり、色素の吸着能が高まったりしたためと考えられる。
更に、上記分散液には、分散液中の上記酸化物半導体微粒子の再凝集を防ぐために、アセチルアセトン、塩酸、硝酸、界面活性剤、キレート剤等を添加してもよく、分散液の増粘のために、ポリエチレンオキシド、ポリビニルアルコール等の高分子やセルロース系の増粘剤等を添加してもよい。
湿式成膜法としては、具体的には、例えば、スクリーンプリント法、インクジェットプリント法、ロールコート法、ドクターブレード法、スピンコート法、スプレー塗布法等が挙げられる。
加熱処理の温度としては、40℃~700℃であるのが好ましく、40℃~650℃であるのが好ましい。また、加熱処理の時間としては、特に制限はないが、通常は10秒~24時間程度である。
化学処理としては、具体的には、例えば、四塩化チタン水溶液を用いた化学メッキ処理、カルボン酸誘導体を用いた化学吸着処理、三塩化チタン水溶液を用いた電気化学的メッキ処理等が挙げられる。
上記対向電極とは、図1に示すように、光電極4に対向して配置される電極5であり、例えば、金属基板、表面に導電膜を有するガラス基板や樹脂基板等を用いることができる。
金属基板としては、白金、金、銀、銅、アルミニウム、インジウム、チタン等の金属を用いることができる。樹脂基板としては、光電極4を構成する透明基板1で例示した基板(フィルム)に加えて、不透明あるいは透明性に劣る一般的な樹脂基板も用いることができる。
また、表面に設ける導電膜としては、白金、金、銀、銅、アルミニウム、インジウム、チタン等の金属;炭素;酸化スズ;アンチモンやフッ素がドープされた酸化スズ;酸化亜鉛;アルミニウムやガリウムがドープされた酸化亜鉛;スズがドープされた酸化インジウム;等の導電性金属酸化物;等が挙げられる。導電膜の厚さや形成方法は、光電極4を構成する透明導電膜2と同様のものを挙げることができる。
導電性高分子としては、具体的には、例えば、ポリチオフェン、ポリピロール、ポリアニリン等が挙げられる。
基板上に導電性高分子膜を形成させる方法は、通常湿式成膜法として知られているディッピング法やスピンコーティング法等を用いて、高分子分散液から基板上に導電高分子膜を形成することができる。
導電性高分子分散液としては、特開2006-169291号公報で開示したポリアニリン分散液や市販品であるポリチオフェン誘導体水分散液(バイトロンP、バイエル社製)、三菱レイヨン社製(アクアセーブ、ポリアニリン誘導体水溶液)等を用いることができる。
また、基板が上記導電基板である場合、上記手法に加えて電解重合法によっても基板上に導電性高分子膜を形成させることができる。導電性高分子フィルム電極は、電解重合法によって電極上に形成された導電性高分子フィルムを電極から剥離した自立性フィルムまたは導電性高分子分散液から通常湿式成膜法として知られているキャスティング法やスピンコーティング法等を用いて形成された自立性フィルム等を用いることもできる。ここで言う導電性高分子分散液は、導電性高分子微粒子が溶媒中に分散している状態と導電性高分子が溶媒中に溶解している状態とが混在しているものを、便宜上導電性高分子分散液としている。
上記電解質層は、図1に示すように、光電極4および対向電極5の間に設けられる電解質層6であり、本発明の光電変換素子においては、上述した本発明の電解質を用いる。
ここで、光増感色素としては、可視光領域および/または赤外光領域に吸収を持つ色素であれば特に限定されなく、金属錯体または有機色素等を用いることができる。
<電解質の調製>
混合容器中で、下記第1表~下記第4表(以下、「第1表等」という。)に示す有機溶媒、層状粘土鉱物等を第1表等に示す組成比で、撹拌し、混合することにより電解質を調製した。
具体的には、第1表等に示す有機溶媒に対して、第1表等に示す組成比で層状粘土鉱物を撹拌しながら添加し、予め層状粘土鉱物を膨潤させ分散させたゲル状物質を得た。
得られたゲル状物質に、第1表等に示す有機塩化合物、ヨウ素、コバルト錯体およびN-メチルベンズイミダゾールを第1表等に示す組成比で、撹拌し、混合した。
透明導電性ガラス(FTOガラス、表面抵抗15Ω/□、日本板硝子社製)上に、酸化チタンペーストTi-Nanoxide D(Solaronix社製)を塗布し、室温下で乾燥させた後、450℃の温度で30分間焼結することにより、透明導電性ガラス上に酸化チタン多孔質膜が形成された光電極を作製した。
作製した光電極を、ルテニウム錯体色素(シス-(ジイソチオシアネート)-N,N′-ビス(2,2′-ビピリジル-4,4′-ジカルボキシリックアシッド)ルテニウム(II)錯体)(Ruthenium 535-bisTBA、Solaronix社製)のブチルアルコール/アセトニトリル溶液(体積比:1/1、濃度3×10-4mol/L)に4時間浸漬させた。
その後、アセトニトリルで洗浄し、暗所において窒素気流下で乾燥することにより光電極の酸化チタン電極に増感色素を担持させたものを光電極として用いた。
光増感色素を担持させた光電極上に調製した上記電解質を塗りつけ、これと、透明導電性ガラス基板(導電面にスズがドープされた酸化インジウム、シート抵抗:8Ω/□、日本板硝子社製)表面にスパッタリング法で厚さ約100nmの白金薄膜を形成させた白金対向電極とを張り合わせた。貼り合せる際、光電極と白金対向電極の間に熱融着フィルムを介在させ、150℃で熱融着させて電極間の封止を行うことにより、色素増感太陽電池(光増感色素:ルテニウム錯体色素1)を得た。
ルテニウム錯体色素として、シス-(ジイソチオシアネート)-(2,2′-ビピリジル-4,4′-ジカルボキシリックアシッド)-(2,2′-ビピリジル-4,4′-ジノニル)ルテニウム(II)錯体(Ruthenium 520-DN、Solaronix社製)を用いた以外は、上記色素増感太陽電池(光増感色素:ルテニウム錯体色素1)と同様の方法で、色素増感太陽電池(光増感色素:ルテニウム錯体色素2)を得た。
ルテニウム錯体色素に代えてインドリン系色素(D149、三菱製紙社製)を用いた以外は色素増感太陽電池(光増感色素:ルテニウム錯体色素)と同様の方法で色素増感太陽電池(光増感色素:有機色素)を作製した。
図2に示すように、光源としてソーラーシミュレーターを用い、AM1.5の擬似太陽光を100mW/cm2の光強度で光電極側から照射し、電流電圧測定装置(ケースレーインスツルメンツ社製デジタルソースメーター2400)を用いて変換効率を求めた。
光電変換効率を測定した色素増感太陽電池を85℃の温度下で、1000時間放置し、その後に上記と同様の方法により光電変換効率を測定し、その維持率(加熱後の光電変換効率/加熱前の光電変換効率)を算出した。
この結果、光電変換効率の維持率が0.80以上であれば、耐熱性に優れていると評価できる。
光電変換効率を測定した色素増感太陽電池を40℃および85%RHの条件下に1000時間放置し、その後に上記と同様の方法により光電変換効率を測定し、その維持率(加湿後の光電変換効率/加湿前の光電変換効率)を算出した。
この結果、光電変換効率の維持率が0.80以上であれば、耐湿性に優れていると評価できる。
光電変換効率を測定した色素増感太陽電池を85℃および85%RHの条件下に1000時間放置し、その後に上記と同様の方法により光電変換効率を測定し、その維持率(加熱・加湿後の光電変換効率/加熱・加湿前の光電変換効率)を算出した。
この結果、光電変換効率の維持率が0.80以上であれば、耐湿熱性に優れていると評価できる。
・有機溶媒A1:メトキシプロピオニトリル(沸点:166℃、比誘電率:25)
・有機溶媒A2:ブトキシプロピオニトリル(沸点:206℃、比誘電率:20)
・有機溶媒A3:プロピレンカーボネート(沸点:240℃、比誘電率:65)
・有機溶媒A4:エチルイソプロピルスルホン(沸点:250℃、比誘電率:32)
・有機溶媒X:アセトニトリル(沸点:82℃、比誘電率:21)
・有機溶媒Y:キノリン(沸点:237℃、比誘電率:9)
・層状粘土鉱物B1:合成スメクタイト(商品名:ルーセンタイトSPN(ルーセンタイトSWN(平均粒径:0.02μm、コープケミカル社製)を有機化処理した有機化層状粘土鉱物)、コープケミカル社製)
・層状粘土鉱物B2:4級アンモニウムおよびアルキルトリアルコキシシランで処理したシラン処理有機ベントナイト(ホージュン社製)
・層状粘土鉱物B3:合成雲母(商品名:ソマシフMPE(ソマシフME(平均粒径:5~7μm、コープケミカル社製)を有機化処理した有機化層状粘土鉱物)、コープケミカル社製)
・有機塩化合物C1:テトラプロピルアンモニウムアイオダイド(東京化成社製)
・有機塩化合物C2:メチルプロピルイミダゾリウムアイオダイド(東京化成社製)
・有機塩化合物C3:ジメチルプロピルイミダゾリウムアイオダイド(東京化成社製)
・有機塩化合物C4:テトラプロピルアンモニウムチオシアネート(Merck社製)
・有機塩化合物C5:グアニジンチオシアネート(アルドリッチ社製)
・有機塩化合物C6:トリヘキシルテトラデシルホスホニウムビス(トリフルオロメチルスルホニル)アミド(アルドリッチ社製)
・コバルト錯体:トリス(2,2′―ビピリジン)コバルトヘキサフルオロホスフェート(アルドリッチ社製)
また、有機溶媒(A)を含有せずに調製した比較例2~6、8~10、12~16および18~20の電解質は、加熱後および加湿後の光電変換効率の維持率が小さく、耐熱性、耐湿性、耐湿熱性に劣ることが分かった。
また、層状粘土鉱物(B)としてアルキルシリル基を有する層状粘土鉱物B2を用いて調製した電解質の方が、耐湿性が更に優れる傾向があることが分かった。
更に、光増感色素としてルテニウム錯体色素1または2を用いた色素増感太陽電池については、有機塩化化合物(C)としてチオシアネートアニオンを有する有機塩化合物C4、C5を配合した実施例4~22の電解質を用いると、耐熱性および耐湿熱性の改善効果があることが分かった。なお、光増感色素として有機色素を用いた色素増感太陽電池については、有機塩化合物C4、C5の有無を問わず、耐熱性および耐湿熱性に優れていることが分かった。
更に、光増感色素としてルテニウム錯体色素2を用いた色素増感太陽電池については、酸化還元対として、ヨウ素の代わりにコバルト錯体を用いた場合であっても、加湿後の光電変換効率の維持率が高く、耐湿性に優れることが分かった(実施例20~22)。
同様に、光増感色素として有機色素を用いた色素増感太陽電池については、ヨウ素の代わりにコバルト錯体を用いた場合であっても、加湿後の光電変換効率の維持率が高く、耐湿性に優れることが分かった(実施例39~41)。
2:透明導電膜
3:酸化物半導体多孔質膜
4:光電極
5:対向電極
6:電解質層
11:透明基板
12:透明導電膜(ITO、FTO)
13:金属酸化物
14:電解質
15:白金薄膜
16:透明導電膜(ITO、FTO)
17:基板
18:対向電極
Claims (7)
- 有機溶媒(A)および層状粘土鉱物(B)を含有する光電変換素子用電解質であって、
前記有機溶媒(A)の沸点が150℃以上であり、比誘電率が20以上である光電変換素子用電解質。 - 前記層状粘土鉱物(B)が、アルキルシリル基を有する請求項1に記載の光電変換素子用電解質。
- 更に、第3級または第4級カチオンを有する有機塩化合物(C)を含有する請求項1または2に記載の光電変換素子用電解質。
- 前記有機塩化合物(C)が、チオシアネートアニオンを有する請求項3に記載の光電変換素子用電解質。
- 前記有機塩化合物(C)が、下記式(1)または(2)で表されるカチオンを有する請求項3または4に記載の光電変換素子用電解質。
(式(1)中、R1は、炭素数1~20のヘテロ原子を含んでいてもよい炭化水素基を表し、炭素数1~20のヘテロ原子を含んでいてもよい置換基を有していてもよい。R2およびR3は、それぞれ独立に水素原子または炭素数1~20の炭化水素基を表し、ヘテロ原子を含んでいてもよい。ただし、窒素原子が二重結合を含む場合、R3は存在しない。式(2)中、Qは、窒素原子、酸素原子、リン原子または硫黄原子を表し、R4、R5、R6およびR7は、それぞれ独立に水素原子または炭素数1~8の炭化水素基を表し、ヘテロ原子を含んでいてもよい。ただし、Qが酸素原子または硫黄原子の場合、R7は存在せず、Qが硫黄原子の場合、R4およびR5は連結していてもよい。) - 透明導電膜および金属酸化物半導体多孔質膜を有する光電極と、
前記光電極に対向して配置される対向電極と、
前記光電極と前記対向電極との間に配された電解質層とを有し、
前記電解質層が、請求項1~5のいずれかに記載の光電変換素子用電解質である光電変換素子。 - 請求項6に記載の光電極に光増感色素を担持させてなる色素増感太陽電池。
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