WO2019116977A1 - 有機光電変換素子の正孔捕集層用組成物 - Google Patents
有機光電変換素子の正孔捕集層用組成物 Download PDFInfo
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- WO2019116977A1 WO2019116977A1 PCT/JP2018/044663 JP2018044663W WO2019116977A1 WO 2019116977 A1 WO2019116977 A1 WO 2019116977A1 JP 2018044663 W JP2018044663 W JP 2018044663W WO 2019116977 A1 WO2019116977 A1 WO 2019116977A1
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- photoelectric conversion
- carbon atoms
- organic photoelectric
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- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- PAYSBLPSJQBEJR-UHFFFAOYSA-N naphtho[2,3-e][1]benzothiole Chemical compound C1=CC=C2C=C3C(C=CS4)=C4C=CC3=CC2=C1 PAYSBLPSJQBEJR-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- 238000007639 printing Methods 0.000 description 1
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- 239000012264 purified product Substances 0.000 description 1
- ZVJDFJRDKIADMB-UHFFFAOYSA-N quinolin-8-ol;sodium Chemical compound [Na].C1=CN=C2C(O)=CC=CC2=C1 ZVJDFJRDKIADMB-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/80—Constructional details
- H10K30/84—Layers having high charge carrier mobility
- H10K30/86—Layers having high hole mobility, e.g. hole-transporting layers or electron-blocking layers
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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 composition for a hole collection layer of an organic photoelectric conversion device.
- the organic photoelectric conversion element is a device that converts light energy into electric energy using an organic semiconductor, and examples thereof include an organic solar cell.
- the organic solar cell is a solar cell element using an organic substance in an active layer and a charge transport material, and is described in M.
- B. a dye-sensitized solar cell developed by Gretzel;
- W. Organic thin film solar cells developed by Tan are well known (Non-Patent Documents 1 and 2).
- the new market is characterized by the fact that it is different from the current mainstream inorganic solar cells, such as light weight, thin film, flexibility, and roll-to-roll production. Formation is expected.
- organic thin film solar cells have characteristics such as electrolyte free and heavy metal compound free, and recently reported that the group of UCLA et al. Has reported 10.6% of photoelectric conversion efficiency (hereinafter abbreviated as PCE). For reasons, it has attracted great attention (Non-Patent Document 3).
- organic thin-film solar cells show high photoelectric conversion efficiency even at low illuminance, and are capable of thinning elements and refining pixels, as compared with existing photoelectric conversion elements using silicon-based materials.
- solar cell applications not only solar cell applications but also light sensor applications such as image sensors are drawing attention because of the feature of being able to combine the properties of color filters etc. (patent documents 1, 2, non-patent document 4 ).
- an organic solar cell a dye-sensitized solar cell and an organic thin film solar cell
- applications such as an optical sensor
- OPV organic photoelectric conversion element
- the organic photoelectric conversion element is configured to include an active layer (photoelectric conversion layer), a charge (hole, electron) collection layer, an electrode (anode, cathode) and the like.
- the active layer and the charge collection layer are generally formed by a vacuum deposition method, but the vacuum deposition method has problems in terms of complexity due to mass production process, cost increase of equipment, utilization efficiency of material, etc. There is.
- a water-dispersible polymer organic conductive material such as PEDOT / PSS may be used as a coating material for the hole collection layer, but the PEDOT / PSS water dispersion has a solid content
- the heat resistance is insufficient and mass production There are various issues left to do.
- the present invention has been made in view of the above circumstances, and provides a thin film having excellent adhesion with an active layer, which is suitable as a hole collection layer of an organic photoelectric conversion device, and in particular, a reverse lamination type organic photoelectric conversion device It is an object of the present invention to provide a composition for a hole collection layer of an organic photoelectric conversion device suitable for the preparation of
- a polymer containing an anilinesulfonic acid substituted by a predetermined electron-donating substituent such as an alkoxy group as a repeating unit has high holes. While exhibiting transportability and low corrosiveness to the active layer, it exhibits high solubility in protic polar solvents such as alcohol and water to form a uniform solution, which is used to form a thin film in the coating process, OPV element
- protic polar solvents such as alcohol and water
- an organic photoelectric conversion device characterized in that it comprises a charge transportable material comprising a polyaniline derivative represented by the formula (1), a fluorine-based surfactant, metal oxide nanoparticles, and a solvent Layer composition,
- R 1 to R 6 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group having 1 to 20 carbon atoms, or a thioalkoxy group having 1 to 20 carbon atoms
- composition for the hole collection layer of the organic photoelectric conversion device according to any one of 1 to 10 wherein the solvent comprises one or more solvents selected from alcohol solvents and water.
- a hole collecting layer comprising the composition for a hole collecting layer of the organic photoelectric conversion device according to any one of 1 to 11, 14.
- a charge transport material comprising a polyaniline derivative represented by the formula (1), an electron accepting dopant material different from the polyaniline derivative represented by the formula (1), a fluorine-based surfactant, metal oxide nano Charge transport composition comprising particles and a solvent
- R 1 to R 6 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group having 1 to 20 carbon atoms, or a thioalkoxy group having 1 to 20 carbon atoms
- the electron accepting dopant substance is an arylsulfonic acid compound represented by the formula (2) (Wherein, X represents O, A represents a naphthalene ring or anthracene ring, B represents a divalent to tetravalent perfluorobiphenyl group, 1 represents the number of sulfonic acid groups bonded to A, It is an integer which satisfy
- the composition for the hole collection layer of the organic photoelectric conversion device of the present invention can be produced only using a charge transporting substance comprising a polyaniline derivative which can be obtained inexpensively in the market or can be easily synthesized by a known method.
- a thin film obtained therefrom is used as a hole collection layer, an organic thin film solar cell excellent in PCE can be obtained.
- a highly uniform thin film can be formed by using the composition for a hole collection layer of the present invention, current leakage is suppressed by using this highly uniform thin film as a hole collection layer, and a reverse bias dark state is obtained. The current can be kept low.
- the charge transportable substance comprising the polyaniline derivative used in the present invention is excellent in the solubility in a protic polar solvent such as alcohol and water, and the composition can be prepared using a solvent which hardly exerts an adverse effect on these active layers.
- the film can be easily formed on the active layer because it contains a fluorosurfactant, and is excellent in adhesion to the active layer because it contains metal oxide nanoparticles. It is also suitable for producing organic thin film solar cells.
- the addition of an electron accepting dopant substance consisting of a Bronsted acid can provide an OPV element exhibiting higher PCE and developing high durability.
- composition for a hole collection layer of the organic photoelectric conversion element of the present invention contains a charge transporting substance comprising a polyaniline derivative represented by the formula (1), a fluorine-based surfactant, and a solvent.
- R 1 to R 6 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group having 1 to 20 carbon atoms, or a thio having 1 to 20 carbon atoms.
- alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group and n-pentyl group
- a linear alkyl group having 1 to 20 carbon atoms such as n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group , Cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group
- alkenyl group having 2 to 20 carbon atoms include ethenyl group, n-1-propenyl group, n-2-propenyl group, 1-methylethenyl group, n-1-butenyl group, n-2-butenyl group, n-3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, n- 1-pentenyl group, n-1-decenyl group, n-1-eicosenyl group etc. are mentioned.
- alkynyl group having 2 to 20 carbon atoms include ethynyl group, n-1-propynyl group, n-2-propynyl group, n-1-butynyl group, n-2-butynyl group, n-3-butynyl group Group, 1-methyl-2-propynyl group, n-1-pentynyl group, n-2-pentynyl group, n-3-pentynyl group, n-4-pentynyl group, 1-methyl-n-butynyl group, 2- Methyl-n-butynyl group, 3-methyl-n-butynyl group, 1,1-dimethyl-n-propynyl group, n-1-hexynyl group, n-1-decynyl group, n-1-pentadecynyl group, n- 1-Eicosinyl group etc. are mentioned.
- alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a c-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, t-butoxy group, n-pentoxy group, n-hexoxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group, n-octadecyloxy group, n-nonadecyloxy group
- thioalkoxy group having 1 to 20 carbon atoms include groups in which the oxygen atom of the above alkoxy group is substituted with a sulfur atom.
- Specific examples of the thioalkoxy (alkylthio) group having 1 to 20 carbon atoms include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, an s-butylthio group and a t-butylthio group.
- n-pentylthio group n-hexylthio group, n-heptylthio group, n-octylthio group, n-nonylthio group, n-decylthio group, n-undecylthio group, n-dodecylthio group, n-tridecylthio group, n-tetradecyl group
- Examples include decylthio group, n-pentadecylthio group, n-hexadecylthio group, n-heptadecylthio group, n-octadecylthio group, n-nonadecylthio group, n-eicosanylthio group and the like.
- haloalkyl group having 1 to 20 carbon atoms examples include groups in which at least one of the hydrogen atoms in the above alkyl group is substituted with a halogen atom.
- the halogen atom may be any of chlorine, bromine, iodine and fluorine atom. Among them, a fluoroalkyl group is preferable, and a perfluoroalkyl group is more preferable.
- fluoromethyl group examples thereof include fluoromethyl group, difluoromethyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, heptafluoropropyl group, 2,2,3,3,3- Pentafluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, nonafluorobutyl group, 4,4,4-trifluoro Butyl group, undecafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, 2,2,3,3,4,4,5,5-octafluoro group Pentyl group, tridecafluorohexyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, 2,2,3,3,4,4,5 , 5, 6, 6-Decafuo Hexyl
- aryl group having 6 to 20 carbon atoms include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group And 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group and the like.
- aralkyl group having 7 to 20 carbon atoms include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl and p-ethylphenylmethyl.
- acyl group having 1 to 20 carbon atoms include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group and benzoyl group.
- one of R 1 to R 4 is a sulfonic acid group, and one or more of R 1 to R 4 remaining, preferably Any one of R 1 to R 4 is an electron donating group, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or the like
- Alkoxy group of 1 to 20, a thioalkoxy group of 1 to 20 carbon atoms, and an alkyl group of 1 to 20 carbon atoms are preferable, an alkoxy group of 1 to 20 carbon atoms is more preferable, and an alkoxy group of 1 to 20 carbon atoms
- R 1 is preferably a sulfonic acid group
- R 4 is preferably an alkoxy group having 1 to 20 carbon atoms.
- R 2 , R 3 , R 5 and R 6 are preferably all hydrogen atoms.
- the weight average molecular weight of the polyaniline derivative represented by the formula (1) is not particularly limited, but in view of the conductivity, the lower limit is usually 200 or more, preferably 1,000 or more as a lower limit. In view of solubility improvement, the upper limit is usually 5,000,000 or less, preferably 500,000 or less. In addition, a weight average molecular weight is a polystyrene conversion value by gel permeation chromatography.
- the polyaniline derivative represented by the formula (1) may be used alone, or two or more compounds may be used in combination.
- the polyaniline derivative represented by Formula (1) may use a commercial item, you may use what was superposed
- the ionization potential of the hole collecting layer is preferably a value close to the ionization potential of the p-type semiconductor material in the active layer.
- the absolute value of the difference is preferably 0 to 1 eV, more preferably 0 to 0.5 eV, and still more preferably 0 to 0.2 eV. Therefore, the composition for a hole collecting layer of the present invention may contain an electron accepting dopant substance for the purpose of adjusting the ionization potential of the charge transporting thin film obtained by using the composition.
- the electron accepting dopant substance is not particularly limited as long as it dissolves in at least one solvent used.
- the electron accepting dopant material include strong inorganic acids such as hydrogen chloride, sulfuric acid, nitric acid and phosphoric acid; aluminum (III) chloride (AlCl 3 ), titanium tetrachloride (IV) (TiCl 4 ), boron tribromide (BBr 3 ), boron trifluoride etherate complex (BF 3 ⁇ OEt 2 ), iron (III) chloride (FeCl 3 ), copper (II) chloride (CuCl 2 ), antimony pentachloride (V) (SbCl 5 ), Lewis acids such as arsenic pentafluoride (V) (AsF 5 ), phosphorus pentafluoride (PF 5 ), tris (4-bromophenyl) aluminum hexachloroantimonate (TBPAH); benzenesulfonic acid, tosyl acid, camphorsulfonic acid , Hydroxybenzenesulfonic acid, 5-sulf, 5-
- a Bronsted acid which donates H + is particularly preferable, an arylsulfonic acid compound is more preferable, and an arylsulfonic acid compound represented by the formula (2) is particularly preferable. It is.
- X represents O
- A represents a naphthalene ring or anthracene ring
- B represents a divalent to tetravalent perfluorobiphenyl group
- 1 represents the number of sulfonic acid groups bonded to A, It is an integer which satisfy
- q shows the number of coupling
- composition of the present invention contains a fluorosurfactant.
- the fluorine-based surfactant is not particularly limited as long as it contains a fluorine atom, and any of cationic, anionic and nonionic surfactants may be used, but a fluorine-based nonionic surfactant is suitable, In particular, at least one fluorinated nonionic surfactant selected from the following formulas (A1) and (B1) is preferable.
- R represents a monovalent organic group containing a fluorine atom
- n represents an integer of 1 to 20.
- the organic group include an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and a heteroaryl group having 2 to 20 carbon atoms.
- heteroaryl group examples include 2-thienyl group, 3-thienyl group, 2-furanyl group, 3-furanyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4 -Isoxazolyl group, 5-isoxazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-imidazolyl group, 4-imidazolyl group, 2 -Pyridyl group, 3-Pyridyl group, 4-Pyridyl group, 2-Pyrazyl group, 3-Pyrazyl group, 5-Pyrazyl group, 6-Pyrazyl group, 2-Pyrimidyl group, 4-Pyrimidyl group, 5-Pyrimidyl group, 6 -Pyrimidyl group, 3-pyr
- alkyl group examples include the same ones as described above.
- n is not particularly limited as long as it is an integer of 1 to 20, but an integer of 1 to 10 is more preferable.
- perfluoroalkylpolyoxyethylene esters represented by the following (A2) having a perfluoroalkyl group R f having 1 to 40 carbon atoms, and perfluoroalkylpolyoxyethylene ethers or fluorotelomer alcohols represented by (B2) More preferred is at least one fluorinated nonionic surfactant selected from
- n represents the same meaning as described above
- the fluorosurfactant used in the present invention can be obtained as a commercial product.
- Neugen FN-1287 etc. Examples include, but are not limited to. In particular, Capstone FS-30, 31, 34, 35, 3100, Neugen FN-1287, which are nonionic surfactants, are preferred.
- the content of the fluorine-based surfactant is not particularly limited, but in consideration of the balance between the improvement of the film formability on the active layer and the decrease of the photoelectric conversion efficiency due to the addition.
- 0.05 to 10% by mass is preferable, 0.05 to 5.0% by mass is more preferable, 0.07 to 2.0% by mass is further more preferable, and 0.10 to 1. 0 mass% is more preferable.
- compositions of the present invention comprise one or more metal oxide nanoparticles.
- Nanoparticles mean microparticles whose average particle size for primary particles is on the order of nanometers (typically less than 500 nm).
- metal oxide nanoparticles are meant metal oxides formed into nanoparticles.
- the primary particle diameter of the metal oxide nanoparticles used in the present invention is not particularly limited as long as it is nanosize, but is preferably 2 to 150 nm in consideration of further enhancing the adhesion to the active layer. 100 nm is more preferable, and 5 to 50 nm is even more preferable.
- a particle diameter is a measured value using the nitrogen adsorption isotherm by BET method.
- the metals constituting the metal oxide nanoparticles in the present invention include semimetals in addition to metals in the usual sense.
- the metal in the ordinary meaning is not particularly limited, but tin (Sn), titanium (Ti), aluminum (Al), zirconium (Zr), zinc (Zn), niobium (Nb), tantalum It is preferable to use one or more selected from the group consisting of Ta) and tungsten (W).
- the term "metalloid” means an element whose chemical and / or physical property is intermediate between metal and nonmetal.
- the element is a semimetal. These semimetals may be used alone or in combination of two or more, or may be used in combination with metals in a usual sense.
- the metal oxide nanoparticles used in the present invention are boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te), tin (Sn), titanium (Ti) It is preferable to contain an oxide of one or more metals selected from aluminum (Al), zirconium (Zr), zinc (Zn), niobium (Nb), tantalum (Ta) and tungsten (W).
- the metal oxide may be a mixture of individual single metal oxides, or a complex oxide containing a plurality of metals.
- the metal oxide examples include B 2 O 3 , B 2 O, SiO 2 , SiO, GeO 2 , GeO, As 2 O 4 , As 2 O 3 , As 2 O 5 , Sb 2 O 3 , Sb 2 Although O 5 , TeO 2 , SnO 2 , ZrO 2 , Al 2 O 3 , ZnO and the like can be mentioned, B 2 O 3 , B 2 O, SiO 2 , SiO, GeO 2 , GeO, As 2 O 4 , As 2 O 3 , As 2 O 5 , SnO 2 , SnO, Sb 2 O 3 , TeO 2 , and mixtures thereof are preferred, and SiO 2 is more preferred.
- the metal oxide nanoparticles may include one or more organic capping groups.
- the organic capping group may be reactive or non-reactive. Examples of reactive organic capping groups include organic capping groups that can be crosslinked by ultraviolet light or radical initiators.
- the compounding amount of the metal oxide nanoparticles is not particularly limited, but considering that the adhesion to the active layer is sufficiently exhibited, 1 to 15 parts of the charge transporting substance can be used. 50% by mass is preferable, and 3 to 40% by mass is more preferable.
- the addition amount of a metal oxide nanoparticle is based on solid content of a charge transportable substance.
- a silica sol in which SiO 2 nanoparticles are dispersed in a dispersion medium is preferable to use, as the metal oxide nanoparticles.
- the silica sol is not particularly limited, and can be appropriately selected from known silica sols and used. Commercially available silica sols are usually in the form of dispersions.
- SiO 2 nanoparticles can be used in various solvents such as water, methanol, methyl ethyl ketone, methyl isobutyl ketone, N, N-dimethyl acetamide, ethylene glycol, isopropanol, methanol, ethylene glycol monopropyl ether, cyclohexanone, acetic acid Those dispersed in ethyl, toluene, propylene glycol monomethyl ether acetate and the like can be mentioned.
- a silica sol in which the dispersion medium is an alcohol solvent or water is preferable, and a silica sol in which the dispersion medium is water is more preferable.
- the alcohol solvent is preferably a water-soluble alcohol, more preferably methanol, 2-propanol or ethylene glycol.
- silica sol Snowtex (registered trademark) ST-O, ST-OS, ST-O-40, ST-OL manufactured by Nissan Chemical Industries, Ltd., Silica Doll 20 manufactured by Nippon Chemical Industrial Co., Ltd. 30, 40, etc.
- Water-dispersed silica sol; methanol silica sol manufactured by Nissan Chemical Industries, Ltd., MA-ST-M, MA-ST-L, IPA-ST, IPA-ST-L, IPA-ST-ZL, EG- Examples include organosilica sols such as ST, but are not limited thereto.
- the solid content concentration of the silica sol is not particularly limited, but is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and still more preferably 15 to 30% by mass.
- the compounding amount of the silica sol is not particularly limited, but it is 5 to 30% by mass with respect to the charge transporting substance in consideration of sufficiently exhibiting the adhesion to the active layer. Preferably, 6 to 25% by mass is more preferable. This compounding amount is also based on the solid content of the charge transporting substance in the same manner as described above.
- the composition of the present invention may also contain an alkoxysilane.
- an alkoxysilane By including an alkoxysilane, the solvent resistance and water resistance of the obtained thin film can be improved, the electron block property can be improved, and the HOMO level and the LUMO level can be made optimum values for the active layer.
- the alkoxysilane may be a siloxane-based material.
- any one or more alkoxysilanes selected from tetraalkoxysilanes, trialkoxysilanes and dialkoxysilanes can be used, and tetraethoxysilane, tetramethoxysilane, phenyltriethoxysilane, phenyltriethoxysilane, and the like.
- Methoxysilane, methyltriethoxysilane, methyltrimethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, dimethyldiethoxysilane, and dimethyldimethoxysilane are preferable, and tetraethoxysilane is more preferable.
- siloxane-based material examples include polysiloxanes such as poly (tetraethoxysilane) and poly (phenylethoxysilane) which are obtained by a reaction such as hydrolysis on the above alkoxysilane.
- the addition amount of the alkoxysilane is not particularly limited as long as the above effects can be exhibited, but it is preferably 0.0001 to 100 times by mass ratio with respect to the polyaniline derivative used in the present invention, 0.01 to 50 Is more preferable and 0.05 to 10 times is even more preferable.
- additives may be blended as long as the object of the present invention can be achieved.
- a kind of additive it can select suitably from well-known things and can be used according to a desired effect.
- the high solubility solvent which can melt
- the high solubility solvents can be used singly or in combination of two or more, and the amount thereof used can be 5 to 100% by mass with respect to the entire solvent used for the composition.
- Examples of such highly soluble solvents include water; alcohol solvents such as ethanol, 2-propanol, 1-butanol, 2-butanol, s-butanol, t-butanol, 1-methoxy-2-propanol and the like; Amide systems such as -methylformamide, N, N-dimethylformamide, N, N-diethylformamide, N-methylacetamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like
- Organic solvents, such as a solvent are mentioned.
- at least one selected from water and alcohol solvents is preferable, and water, ethanol and 2-propanol are more preferable.
- a solvent consisting of only one or two or more solvents selected from alcohol solvents and water that does not adversely affect the active layer is used. It is preferred to use.
- the charge transporting substance and the electron accepting dopant substance are preferably both completely dissolved or uniformly dispersed in the above-mentioned solvent, and it is preferable to provide an organic thin film solar cell with high conversion efficiency. It is more preferable that these substances be completely dissolved in the above solvent, in consideration of obtaining the pore collection layer reproducibly.
- the composition for a hole collection layer of the present invention has a viscosity of 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., in order to improve film formability and dischargeability from a coating apparatus.
- At least one high-viscosity organic solvent having a boiling point of 50 to 300 ° C., preferably 150 to 250 ° C., at normal pressure may be contained.
- the high viscosity organic solvent is not particularly limited, and examples thereof include cyclohexanol, ethylene glycol, 1,3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, and 1,3-butane. Diol, 2,3-butanediol, 1,4-butanediol, propylene glycol, hexylene glycol and the like can be mentioned.
- the addition ratio of the high-viscosity organic solvent to the whole solvent used in the composition of the present invention is preferably in the range in which the solid does not precipitate, and the addition ratio is 5 to 80% by mass as long as the solid does not precipitate. Is preferred.
- a solvent using in the composition another solvent capable of imparting film flatness during heat treatment. It is also possible to mix in a proportion of 1 to 90% by mass, preferably 1 to 50% by mass, based on the whole.
- solvent for example, butyl cellosolve, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl carbitol, Diacetone alcohol, ⁇ -butyrolactone, ethyl lactate, n-hexyl acetate and the like can be mentioned.
- the solid content concentration of the composition of the present invention is appropriately set in consideration of the viscosity and surface tension of the composition, the thickness of the thin film to be produced, etc., but it is usually 0.1 to 10.0 mass. %, Preferably 0.5 to 5.0% by mass, more preferably 1.0 to 3.0% by mass. Also, the mass ratio of the charge transporting substance to the electron accepting dopant substance is appropriately set in consideration of the types of charge transporting property, charge transporting substance and the like to be expressed, but usually the charge transporting substance 1 On the other hand, the electron accepting dopant substance is 0 to 10, preferably 0.1 to 3.0, more preferably 0.2 to 2.0.
- the viscosity of the composition for a hole collecting layer used in the present invention is appropriately adjusted in accordance with the coating method in consideration of the thickness of the thin film to be produced and the solid content concentration, but it is usually 25.degree. It is about 0.1 mPa ⁇ s to 50 mPa ⁇ s.
- the charge transporting substance, the electron accepting dopant substance, the solvent and the like can be mixed in any order as long as the solid content is uniformly dissolved or dispersed in the solvent. That is, for example, a method of dissolving a polyaniline derivative in a solvent and then dissolving the electron accepting dopant substance in the solution, a method of dissolving the electron accepting dopant substance in a solvent and then dissolving the polyaniline derivative in the solution, After mixing the polyaniline derivative and the electron accepting dopant substance, any method of introducing and dissolving the mixture in a solvent can be employed as long as the solid content is uniformly dissolved or dispersed in the solvent.
- the order of addition of a fluorine-based surfactant, metal oxide nanoparticles and the like is also arbitrary.
- preparation of the composition is carried out under an inert gas atmosphere at normal temperature and pressure, but unless the compounds in the composition are decomposed or the composition is greatly changed Below) or while heating.
- the hole collection of the present invention is performed by applying the composition described above on the anode in the case of a sequentially stacked organic thin film solar cell, and on the active layer in the case of a reversed stacked organic thin film solar cell Can form a layer.
- the thickness of the desired thin film, etc. drop casting, spin coating, blade coating, dip coating, roll coating, bar coating, die coating, Among various wet process methods such as an inkjet method and a printing method (a letterpress, intaglio, lithography, screen printing, etc.), an optimum one may be adopted.
- coating is carried out under an inert gas atmosphere at normal temperature and pressure, but in the atmosphere (in the presence of oxygen) unless the compounds in the composition are decomposed or the composition changes significantly. You may carry out and you may carry out with heating.
- the film thickness is not particularly limited, but in any case, it is preferably about 0.1 to 500 nm, and more preferably about 1 to 100 nm.
- a method of changing the film thickness there are methods such as changing the solid content concentration in the composition or changing the amount of solution at the time of application.
- Ordered stacked organic thin film solar cell Step of forming a layer of anode material on the surface of a transparent substrate to manufacture a transparent electrode
- an anode material indium tin oxide (ITO), indium Inorganic oxides such as zinc oxide (IZO), metals such as gold, silver and aluminum, and high charge transporting organic compounds such as polythiophene derivatives and polyaniline derivatives can be used.
- ITO indium tin oxide
- IZO indium Inorganic oxides
- metals such as gold, silver and aluminum
- high charge transporting organic compounds such as polythiophene derivatives and polyaniline derivatives
- the transparent substrate a substrate made of glass or transparent resin can be used.
- the formation method of the layer (anode layer) of anode material is suitably selected according to the property of anode material.
- dry processes such as vacuum deposition and sputtering are selected in the case of poorly soluble or poorly dispersible sublimable materials, and in the case of solution materials or dispersion materials, the viscosity and surface tension of the composition are desired.
- An optimum one of the various wet process methods described above is adopted in consideration of the thickness of the thin film and the like.
- a commercially available transparent anode substrate can also be used, and in this case, it is preferable to use a substrate which has been subjected to a smoothing treatment from the viewpoint of improving the yield of the device.
- the method for producing an organic thin film solar cell of the present invention does not include the step of forming an anode layer.
- a transparent anode substrate using inorganic oxides, such as ITO, as an anode material it is preferable to wash
- a surface treatment such as UV ozone treatment or oxygen-plasma treatment immediately before use.
- the anode material contains an organic substance as a main component, the surface treatment may not be performed.
- the active layer is an n layer which is a thin film made of an n-type semiconductor material and a p which is a thin film made of a p-type semiconductor material. It may be a laminate of layers or a non-laminate thin film composed of a mixture of these materials.
- n-type semiconductor materials include fullerene, [6,6] -phenyl-C 61 -butyric acid methyl ester (PC 61 BM), [6,6] -phenyl-C 71 -butyric acid methyl ester (PC 71 BM), etc.
- regioregular poly (3-hexylthiophene) P3HT
- PTB7 regioregular poly (3-hexylthiophene)
- JP-A 2009-158921 and WO 2010/008672 polymers containing a thiophene skeleton in the main chain, phthalocyanines such as CuPC and ZnPC, and porphyrins such as tetrabenzoporphyrin.
- PC 61 BM and PC 71 BM are preferable as the n-type material, and polymers having a thiophene skeleton in the main chain such as PTB 7 are preferable as the p-type material.
- thiophene backbone in the main chain refers to a divalent aromatic ring consisting of only thiophene, or thienothiophene, benzothiophene, dibenzothiophene, benzodithiophene, naphthothiophene, naphthodithiophene, anthrathiophene, anthradi It represents a divalent fused aromatic ring containing one or more thiophenes such as thiophene and the like, which may be substituted by the substituents shown by the above R 1 to R 6 .
- the various dry processes described above are selected when the active layer material is a poorly soluble sublimation material as described above, and in the case of a solution material or a dispersion material, the viscosity and surface of the composition
- An optimum one of the various wet process methods described above is adopted in consideration of the tension, the desired thickness of the thin film, and the like.
- Electron Collecting Layer Step of Forming Electron Collecting Layer on Active Layer Formed Between the active layer and the cathode layer for the purpose of, for example, efficient transfer of charges, if necessary. You may form an electron collection layer.
- lithium oxide Li 2 O
- magnesium oxide MgO
- alumina Al 2 O 3
- lithium fluoride LiF
- sodium fluoride NaF
- magnesium fluoride MgF 2
- strontium fluoride SrF 2
- cesium carbonate Cs 2 CO 3
- 8-quinolinol lithium salt Liq
- 8-quinolinol sodium salt Naq
- vasocuproin BCP
- 4,7-diphenyl And -1,10-phenanthroline BPhen
- PEI polyethylene imine
- PEIE ethoxylated polyethylene imine
- the electron collection material is a sparingly soluble sublimable material as described above, and in the case of a solution material or a dispersion liquid material, Among the various wet process methods described above, the most suitable one is adopted in consideration of viscosity, surface tension, desired thin film thickness and the like.
- Step of Forming a Cathode Layer on the Formed Electron Collection Layer As a cathode material, aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium, calcium, Metals such as barium, silver and gold, inorganic oxides such as indium tin oxide (ITO) and indium zinc oxide (IZO), and high charge transporting organic compounds such as polythiophene derivatives and polyaniline derivatives
- ITO indium tin oxide
- IZO indium zinc oxide
- high charge transporting organic compounds such as polythiophene derivatives and polyaniline derivatives
- the cathode materials of the above can be laminated or mixed and used.
- the various dry processes described above are selected when the cathode layer material is poorly soluble or poorly dispersible sublimable material as described above, and in the case of solution material or dispersion material, the composition Among the various wet process methods described above, the most suitable one is adopted in consideration of the viscosity, surface tension, desired thin film thickness and the like.
- a carrier block layer may be provided between arbitrary layers for the purpose of controlling the rectifying property of the photocurrent or the like.
- an electron block layer is inserted between the active layer and the hole collection layer or the anode
- a hole block layer is inserted between the active layer and the electron collection layer or the cathode.
- materials for forming the hole blocking layer include titanium oxide, zinc oxide, tin oxide, vasocuproin (BCP), 4,7-diphenyl 1, 10-phenanthroline (BPhen) and the like.
- Materials forming the electron blocking layer include triarylamines such as N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (.alpha.-NPD) and poly (triarylamine) (PTAA) Materials etc. may be mentioned.
- the various dry processes described above are selected in the case where the carrier block layer material is poorly soluble or poorly dispersible sublimable material as described above, and in the case of solution material or dispersion liquid material Among the various wet process methods described above, the most suitable one is adopted in consideration of the viscosity and surface tension of the composition, the desired thickness of the thin film, and the like.
- Step of forming a layer of cathode material on the surface of a transparent substrate to manufacture a transparent cathode substrate In addition to the exemplified ones, fluorine-doped tin oxide (FTO) can be mentioned, and as the transparent substrate, ones exemplified for the above-mentioned order laminated type anode material can be mentioned.
- FTO fluorine-doped tin oxide
- the method of forming the layer of the cathode material is also the above-mentioned dry process in the case of a poorly soluble or poorly dispersible sublimable material, and in the case of a solution material or a dispersion material, the viscosity of the composition and Among the various wet process methods described above, the most suitable one is adopted in consideration of surface tension, desired thin film thickness and the like. Also in this case, a commercially available transparent cathode substrate can be suitably used, and from the viewpoint of improving the yield of the device, it is preferable to use a substrate which has been subjected to a smoothing treatment.
- the method for producing an organic thin film solar cell of the present invention does not include the step of forming a cathode layer.
- an inorganic oxide is used as a cathode material to form a transparent cathode substrate, the same cleaning treatment or surface treatment as the sequentially layered anode material may be applied.
- Electron Collection Layer Step of Forming an Electron Collection Layer on the Formed Cathode If necessary, an electron between the active layer and the cathode layer for the purpose of efficient transfer of charge, etc. You may form a collection layer.
- the material for forming the electron collection layer include zinc oxide (ZnO), titanium oxide (TiO), tin oxide (SnO), and the like, in addition to those exemplified for the above-described materials of the regular stack type.
- the method of forming the electron collection layer is also selected from the above-mentioned dry process in the case of a poorly soluble or poorly dispersible sublimable material, and in the case of a solution material or dispersion material, the viscosity and surface tension of the composition, Among the various wet process methods described above, the most suitable one is adopted in consideration of the thickness of the thin film to be formed.
- a precursor layer of an inorganic oxide may be formed on the cathode by a wet process (in particular, spin coating or slit coating) and fired to form an inorganic oxide layer.
- the active layer is an n layer which is a thin film made of an n-type semiconductor material and a p layer which is a thin film made of a p-type semiconductor material And a non-laminated thin film made of a mixture of these materials.
- the n-type and p-type semiconductor materials include the same ones as exemplified for the above-mentioned stacked semiconductor materials.
- the n-type materials PC 61 BM and PC 71 BM can be used as the p-type material.
- polymers containing a thiophene skeleton in the main chain such as PTB7 are preferred.
- the method of forming the active layer is also the same as the method described for the above-described sequentially stacked active layer.
- Step of Forming Anode Layer on Formed Hole Collection Layer As the anode material, the same materials as the above-mentioned orderly laminated type anode material may be mentioned, and as a method of forming the anode layer Is also similar to the sequentially laminated cathode layer.
- a carrier block layer may be provided between arbitrary layers for the purpose of controlling the rectifying property of the photocurrent or the like, as required, as in the case of the forward stacked element.
- Examples of the material for forming the hole blocking layer and the material for forming the electron blocking layer include the same as described above, and the method for forming the carrier blocking layer is also the same as described above.
- the OPV device manufactured by the method exemplified above is introduced again into the glove box and sealed in an inert gas atmosphere such as nitrogen to prevent the device deterioration due to the atmosphere, and the device is sealed A function as a solar cell can be exhibited, and measurement of solar cell characteristics can be performed.
- a sealing method a method of allowing a concave glass substrate having a UV curing resin attached to the end portion to adhere to the film forming surface side of an organic thin film solar cell element in an inert gas atmosphere and curing the resin by UV irradiation And film-sealing type sealing by a method such as sputtering under a vacuum.
- Example 1-1 47.5 mg of arylsulfonic acid compound A represented by the above formula (2-1) synthesized based on the description of WO 2006/025342 (the same applies hereinafter) is dissolved in 3.16 g of distilled water, aquaPASS-01X ( Add 1.86 g of Mitsubishi Chemical Co., Ltd., 5.1% by mass aqueous solution, 36.8 mg of Snowtex ST-O (Nissan Chemical Co., Ltd., 20.4% by mass aqueous dispersion) and 4.90 g of ethanol Thus, a brown solution with a concentration of 1.5% by mass was prepared.
- a fluorinated nonionic surfactant (FN-1287, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) is added to the obtained brown solution at 0.7% by mass with respect to the entire brown solution, and a syringe with a pore diameter of 0.45 ⁇ m It filtered by the filter and obtained composition B1 for positive hole collection layers.
- Embodiment 1-2 45.0 mg of arylsulfonic acid compound A represented by the above formula (2-1) is dissolved in 3.25 g of distilled water, and aquaPASS-01X (manufactured by Mitsubishi Chemical Corporation, 5.1% by mass aqueous solution) 1.77 g, Snow 73.5 mg of Tex ST-O (manufactured by Nissan Chemical Industries, Ltd., 20.4% by mass aqueous dispersion) and 4.87 g of ethanol were added to prepare a brownish brown solution having a concentration of 1.5% by mass.
- aquaPASS-01X manufactured by Mitsubishi Chemical Corporation, 5.1% by mass aqueous solution
- Snow 73.5 mg of Tex ST-O manufactured by Nissan Chemical Industries, Ltd., 20.4% by mass aqueous dispersion
- 4.87 g of ethanol were added to prepare a brownish brown solution having a concentration of 1.5% by mass.
- a fluorinated nonionic surfactant (FN-1287, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) is added to the obtained brown solution at 0.7% by mass with respect to the entire brown solution, and a syringe with a pore diameter of 0.45 ⁇ m It filtered by the filter and obtained composition B2 for positive hole collection layers.
- Embodiment 1-3 40.0 mg of arylsulfonic acid compound A represented by the above formula (2-1) is dissolved in 3.44 g of distilled water, and aquaPASS-01X (manufactured by Mitsubishi Chemical Corporation, 5.1% by mass aqueous solution) 1.57 g, Snow 147 mg of Tex ST-O (manufactured by Nissan Chemical Industries, Ltd., 20.4% by mass aqueous dispersion) and 4.81 g of ethanol were added to prepare a brownish brown solution having a concentration of 1.5% by mass.
- aquaPASS-01X manufactured by Mitsubishi Chemical Corporation, 5.1% by mass aqueous solution
- Snow 147 mg of Tex ST-O manufactured by Nissan Chemical Industries, Ltd., 20.4% by mass aqueous dispersion
- 4.81 g of ethanol were added to prepare a brownish brown solution having a concentration of 1.5% by mass.
- a fluorinated nonionic surfactant (FN-1287, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) is added to the obtained brown solution at 0.7% by mass with respect to the entire brown solution, and a syringe with a pore diameter of 0.45 ⁇ m It filtered by the filter and obtained composition B3 for positive hole collection layers.
- Comparative Example 1-1 100 mg of arylsulfonic acid compound A represented by the above formula (2-1) is dissolved in 6.13 g of distilled water, and aquaPASS-01X (manufactured by Mitsubishi Chemical Corporation, 5.1% by mass aqueous solution) 3.92 g and ethanol9. 85 g was added to prepare a dark blue solution having a concentration of 1.5% by mass.
- a fluorinated nonionic surfactant (FN-1287, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) is added to the obtained brown solution at 0.7% by mass with respect to the entire brown solution, and a syringe with a pore diameter of 0.45 ⁇ m The mixture was filtered with a filter to obtain a composition C1 for a hole collection layer.
- composition B1 for a hole collection layer prepared in Example 1-1 is applied on the active layer by a spin coating method, and then using a hot plate at 60 ° C. for 30 minutes, and further at 80 ° C. for 10 minutes
- the hole collection layer was formed by annealing treatment.
- the film thickness of the hole collection layer was about 50 nm.
- Embodiment 2-2 A laminate for an adhesion test was produced in the same manner as in Example 2-1 except that the composition B2 for hole collection layer was used instead of the composition B1 for hole collection layer.
- Example 2-3 A laminate for an adhesion test was produced in the same manner as in Example 2-1 except that the composition B3 for hole collection layer was used instead of the composition B1 for hole collection layer.
- Comparative Example 2-1 A laminate for an adhesion test was produced in the same manner as in Example 2-1 except that the composition C1 for hole collection layer was used instead of the composition B1 for hole collection layer.
- Adhesion Test A peeling test was conducted on the laminates produced in the above Examples 2-1 to 2-3 and Comparative Example 2-1. The peeling test was performed according to JIS K 5600-5-6. After making six cuts in a 2 mm sense in the film to be evaluated longitudinally and laterally, a cellophane tape having a width of 18 mm and an adhesion strength of 4 N / cm was attached to the film surface, and peeling was performed in the direction of about 60 °. The degree of adhesion between the substrate surface and the cellophane tape surface after peeling was visually observed to evaluate adhesion. The results are shown in Table 1.
- the composition B1 for a hole collection layer prepared in Example 1-1 was applied on the active layer by a spin coating method, and then dried at room temperature to form a hole collection layer.
- the film thickness of the hole collection layer was about 50 nm.
- the laminated substrate is placed in a vacuum evaporation apparatus, the vacuum in the apparatus is reduced to 1 ⁇ 10 -3 Pa or less, and the silver layer to be an anode is 80 nm thick by resistance heating.
- annealing was performed by heating at 60 ° C. for 30 minutes using a hot plate.
- Examples 3-2 to 3-3 A reverse laminated OPV element was produced in the same manner as in Example 3-1 except that the composition B2 to B3 for hole collection layer was used instead of the composition B1 for hole collection layer.
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Abstract
Description
有機太陽電池は、活性層や電荷輸送物質に有機物を使用した太陽電池素子であり、M.グレッツェルによって開発された色素増感太陽電池と、C.W.タンによって開発された有機薄膜太陽電池とがよく知られている(非特許文献1,2)。
いずれも軽量・薄膜で、フレキシブル化可能である点、ロール・トゥ・ロールでの生産が可能である点など、現在主流の無機系太陽電池とは異なる特長を持っていることから、新たな市場形成が期待されている。
中でも、有機薄膜太陽電池は、電解質フリー、重金属化合物フリー等の特長を持つうえに、最近、UCLAらのグループによって光電変換効率(以下PCEと略す)10.6%の報告がなされたことなどの理由から、大きな注目を集めている(非特許文献3)。
有機光電変換素子は、活性層(光電変換層)、電荷(正孔、電子)捕集層、および電極(陽極、陰極)等を備えて構成される。
これらの中でも活性層および電荷捕集層は、一般に真空蒸着法によって形成されているが、真空蒸着法には、量産プロセスによる複雑性、装置の高コスト化、材料の利用効率等の点で問題がある。
1. 式(1)で表されるポリアニリン誘導体からなる電荷輸送性物質と、フッ素系界面活性剤と、金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする有機光電変換素子の正孔捕集層用組成物、
mおよびnは、それぞれ、0≦m≦1、0≦n≦1、かつ、m+n=1を満たす数である。}
2. 前記金属酸化物ナノ粒子が、SiO2である1の有機光電変換素子の正孔捕集層用組成物、
3. 前記SiO2が、シリカゾルである2の有機光電変換素子の正孔捕集層用組成物、
4. 前記シリカゾルの分散媒が水である3の有機光電変換素子の正孔捕集層用組成物、
5. 前記フッ素系界面活性剤が、フッ素系ノニオン性界面活性剤である1~4のいずれかの有機光電変換素子の正孔捕集層用組成物、
6. 前記フッ素系ノニオン性界面活性剤が、下記式(A2)および(B2)から選ばれる少なくとも1種である5の有機光電変換素子の正孔捕集層用組成物、
7. 前記R1が、スルホン酸基であり、前記R4が、炭素数1~20のアルコキシ基である1~6のいずれかの有機光電変換素子の正孔捕集層用組成物、
8. 前記式(1)で表されるポリアニリン誘導体とは異なる電子受容性ドーパント物質を含む1~7のいずれかの有機光電変換素子の正孔捕集層用組成物、
9. 前記電子受容性ドーパント物質が、ブレンステッド酸である8の有機光電変換素子の正孔捕集層用組成物、
10. 前記電子受容性ドーパント物質が、式(2)で表されるアリールスルホン酸化合物である9の有機光電変換素子の正孔捕集層用組成物、
11. 前記溶媒が、アルコール系溶媒および水から選ばれる1種または2種以上の溶媒を含む1~10のいずれかの有機光電変換素子の正孔捕集層用組成物、
12. 前記有機光電変換素子が、有機薄膜太陽電池、色素増感太陽電池または光センサーである1~11のいずれかの有機光電変換素子の正孔捕集層用組成物、
13. 1~11のいずれかの有機光電変換素子の正孔捕集層用組成物を用いてなる正孔捕集層、
14. 13の正孔捕集層を有する有機光電変換素子、
15. 13の正孔捕集層と、それに接するように設けられた活性層とを有する有機光電変換素子、
16. 前記活性層が、フラーレン誘導体を含む14または15の有機光電変換素子、
17. 前記活性層が、主鎖にチオフェン骨格を含むポリマーを含む14または15の有機光電変換素子、
18. 前記活性層が、フラーレン誘導体および主鎖にチオフェン骨格を含むポリマーを含む14または15の有機光電変換素子、
19. 逆積層型である14~18のいずれかの有機光電変換素子、
20. 前記有機光電変換素子が、有機薄膜太陽電池、色素増感太陽電池または光センサーである14~19のいずれかの有機光電変換素子、
21. トップ陽極構造を有する20の有機光電変換素子、
22. 式(1)で表されるポリアニリン誘導体からなる電荷輸送性物質と、この式(1)で表されるポリアニリン誘導体とは異なる電子受容性ドーパント物質と、フッ素系界面活性剤と、金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする電荷輸送性組成物、
23. 前記電子受容性ドーパント物質が、式(2)で表されるアリールスルホン酸化合物である22の電荷輸送性組成物
を提供する。
また、本発明で用いるポリアニリン誘導体からなる電荷輸送性物質は、アルコールや水等のプロトン性極性溶媒に対する溶解性に優れ、これらの活性層に悪影響を与えにくい溶媒を用いて組成物を調製でき、しかも、フッ素系界面活性剤を含んでいるため活性層上に容易に成膜できるとともに、金属酸化物ナノ粒子を含んでいるため活性層との密着性にも優れていることから、逆積層型有機薄膜太陽電池の作製にも適している。
さらに、ブレンステッド酸からなる電子受容性ドーパント物質を添加することで、より高いPCEを示し、高耐久性を発現するOPV素子が得られる。
本発明の有機光電変換素子の正孔捕集層用組成物は、式(1)で表されるポリアニリン誘導体からなる電荷輸送性物質と、フッ素系界面活性剤と、溶媒とを含む。
炭素数1~20のアルキル基の具体例としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、n-ノニル基、n-デシル基等の炭素数1~20の鎖状アルキル基;シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデシル基、ビシクロブチル基、ビシクロペンチル基、ビシクロヘキシル基、ビシクロヘプチル基、ビシクロオクチル基、ビシクロノニル基、ビシクロデシル基等の炭素数3~20の環状アルキル基等が挙げられる。
炭素数1~20のチオアルコキシ(アルキルチオ)基の具体例としては、メチルチオ基、エチルチオ基、n-プロピルチオ基、イソプロピルチオ基、n-ブチルチオ基、イソブチルチオ基、s-ブチルチオ基、t-ブチルチオ基、n-ペンチルチオ基、n-ヘキシルチオ基、n-ヘプチルチオ基、n-オクチルチオ基、n-ノニルチオ基、n-デシルチオ基、n-ウンデシルチオ基、n-ドデシルチオ基、n-トリデシルチオ基、n-テトラデシルチオ基、n-ペンタデシルチオ基、n-ヘキサデシルチオ基、n-ヘプタデシルチオ基、n-オクタデシルチオ基、n-ノナデシルチオ基、n-エイコサニルチオ基等が挙げられる。
その具体例としては、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、2,2,2-トリフルオロエチル基、ヘプタフルオロプロピル基、2,2,3,3,3-ペンタフルオロプロピル基、2,2,3,3-テトラフルオロプロピル基、2,2,2-トリフルオロ-1-(トリフルオロメチル)エチル基、ノナフルオロブチル基、4,4,4-トリフルオロブチル基、ウンデカフルオロペンチル基、2,2,3,3,4,4,5,5,5-ノナフルオロペンチル基、2,2,3,3,4,4,5,5-オクタフルオロペンチル基、トリデカフルオロヘキシル基、2,2,3,3,4,4,5,5,6,6,6-ウンデカフルオロヘキシル基、2,2,3,3,4,4,5,5,6,6-デカフルオロヘキシル基、3,3,4,4,5,5,6,6,6-ノナフルオロヘキシル基等が挙げられる。
炭素数1~20のアシル基の具体例としては、ホルミル基、アセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基、ベンゾイル基等が挙げられる。
置換位置は特に限定されるものではないが、本発明では、R1がスルホン酸基であることが好ましく、また、R4が炭素数1~20のアルコキシ基であることが好ましい。
さらに、R2、R3、R5およびR6は、いずれも水素原子であることが好ましい。
また、式(1)で表されるポリアニリン誘導体は、市販品を用いても、アニリン誘導体などを出発原料とした公知の方法によって重合したものを用いてもよいが、いずれの場合も再沈殿やイオン交換等の方法により精製されたものを用いることが好ましい。精製したものを用いることで、当該化合物を含む組成物から得られた薄膜を備えたOPV素子の特性をより高めることができる。
したがって、本発明の正孔捕集層用組成物には、これを用いて得られる電荷輸送性薄膜のイオン化ポテンシャルを調節することを目的として、電子受容性ドーパント物質を含んでいてもよい。
電子受容性ドーパント物質としては、使用する少なくとも1種の溶媒に溶解するものであれば、特に限定されない。
フッ素系界面活性剤としては、フッ素原子を含有している限り特に限定されるものではなく、カチオン性、アニオン性、ノニオン性のいずれでもよいが、フッ素系ノニオン性界面活性剤が好適であり、特に、下記式(A1)および(B1)から選ばれる少なくとも1種のフッ素系ノニオン性界面活性剤が好ましい。
有機基の具体例としては、炭素数1~40のアルキル基、炭素数6~20のアリール基、炭素数7~20のアラルキル基、炭素数2~20のヘテロアリール基等が挙げられる。
ヘテロアリール基の具体例としては、2-チエニル基、3-チエニル基、2-フラニル基、3-フラニル基、2-オキサゾリル基、4-オキサゾリル基、5-オキサゾリル基、3-イソオキサゾリル基、4-イソオキサゾリル基、5-イソオキサゾリル基、2-チアゾリル基、4-チアゾリル基、5-チアゾリル基、3-イソチアゾリル基、4-イソチアゾリル基、5-イソチアゾリル基、2-イミダゾリル基、4-イミダゾリル基、2-ピリジル基、3-ピリジル基、4-ピリジル基、2-ピラジル基、3-ピラジル基、5-ピラジル基、6-ピラジル基、2-ピリミジル基、4-ピリミジル基、5-ピリミジル基、6-ピリミジル基、3-ピリダジル基、4-ピリダジル基、5-ピリダジル基、6-ピリダジル基、1,2,3-トリアジン-4-イル基、1,2,3-トリアジン-5-イル基、1,2,4-トリアジン-3-イル基、1,2,4-トリアジン-5-イル基、1,2,4-トリアジン-6-イル基、1,3,5-トリアジン-2-イル基等が挙げられる。
その他、アルキル基、アリール基、アラルキル基の具体例としては、上記と同様のものが挙げられる。
上記nは、1~20の整数であれば、特に限定されるものではないが、1~10の整数がより好ましい。
そのような市販品としては、デュポン製キャップストーン(Capstone,登録商標)FS-10、FS-22、FS-30、FS-31、FS-34、FS-35、FS-50、FS-51、FS-60、FS-61、FS-63、FS-64、FS-65、FS-66、FS-81、FS-83、FS-3100;第一工業製薬(株)製ノイゲンFN-1287等が挙げられるが、これらに限定されるものではない。
特に、ノニオン性界面活性剤である、キャップストーンFS-30、31、34、35、3100、ノイゲンFN-1287が好適である。
本発明で用いる金属酸化物ナノ粒子の一次粒子径は、ナノサイズであれば特に限定されるものではないが、活性層に対する密着性をより高めることを考慮すると、2~150nmが好ましく、3~100nmがより好ましく、5~50nmがより一層好ましい。なお、粒子径は、BET法による窒素吸着等温線を用いた測定値である。
通常の意味での金属としては、特に限定されるものではないが、スズ(Sn)、チタン(Ti)、アルミニウム(Al)、ジルコニウム(Zr)、亜鉛(Zn)、ニオブ(Nb)、タンタル(Ta)およびタングステン(W)からなる群より選択される1種または2種以上を用いることが好ましい。
一方、半金属とは、化学的および/または物理的性質が金属と非金属の中間である元素を意味する。半金属の普遍的な定義は確立されていないが、本発明では、ホウ素(B)、ケイ素(Si)、ゲルマニウム(Ge)、ヒ素(As)、アンチモン(Sb)およびテルル(Te)の計6元素を半金属とする。これらの半金属は、単独で用いても、2種以上を組み合わせて用いてもよく、また通常の意味での金属と組み合わせて用いてもよい。
なお、電荷輸送性物質を溶液や分散液として用いる場合、金属酸化物ナノ粒子の添加量は、電荷輸送性物質の固形分量を基準とする。
シリカゾルとしては、特に限定されるものではなく、公知のシリカゾルから適宜選択して用いることができる。
市販のシリカゾルは通常、分散液の形態にある。市販のシリカゾルとしては、SiO2ナノ粒子が種々の溶媒、例えば、水、メタノール、メチルエチルケトン、メチルイソブチルケトン、N,N-ジメチルアセトアミド、エチレングリコール、イソプロパノール、メタノール、エチレングリコールモノプロピルエーテル、シクロヘキサノン、酢酸エチル、トルエン、プロピレングリコールモノメチルエーテルアセタート等に分散したものが挙げられる。
特に、本発明においては、分散媒がアルコール溶媒または水であるシリカゾルが好ましく、分散媒が水であるシリカゾルがより好ましい。アルコール溶媒としては、水溶性のアルコールが好ましく、メタノール、2-プロパノール、エチレングリコールがより好ましい。
また、シリカゾルの固形分濃度も特に限定されるものではないが、5~60質量%が好ましく、10~50質量%がより好ましく、15~30質量%がより一層好ましい。
なお、この配合量も、上記と同様に電荷輸送性物質の固形分量を基準とする。
アルコキシシランとしては、テトラアルコキシシラン、トリアルコキシシラン、ジアルコキシシランの中から任意の1種以上のアルコキシシランを用いることができるが、特にテトラエトキシシラン、テトラメトキシシラン、フェニルトリエトキシシラン、フェニルトリメトキシシラン、メチルトリエトキシシラン、メチルトリメトキシシラン、3,3,3-トリフルオロプロピルトリメトキシシラン、ジメチルジエトキシシラン、ジメチルジメトキシシランが好ましく、テトラエトキシシランがより好ましい。
シロキサン系材料としては、上記アルコキシシランに対して加水分解等の反応により得られる、ポリ(テトラエトキシシラン)、ポリ(フェニルエトキシシラン)等のポリシロキサンが挙げられる。
アルコキシシランの添加量としては、上記の効果が発揮される量であれば特に限定されないが、本発明で用いるポリアニリン誘導体に対し、質量比で0.0001~100倍が好ましく、0.01~50倍がより好ましく、0.05~10倍がより一層好ましい。
添加剤の種類としては、所望の効果に応じて公知のものから適宜選択して用いることができる。
これらの中でも、水およびアルコール系溶媒から選ばれる少なくとも1種が好ましく、水、エタノール、2-プロパノールがより好ましい。
特に、逆積層型のOPVの正孔捕集層の形成に用いる場合には、活性層に悪影響を与えない、アルコール系溶媒および水から選ばれる1種または2種以上の溶媒のみからなる溶媒を用いることが好ましい。
高粘度有機溶媒としては、特に限定されるものではなく、例えば、シクロヘキサノール、エチレングリコール、1,3-オクチレングリコール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール、1,3-ブタンジオール、2,3-ブタンジオール、1,4-ブタンジオール、プロピレングリコール、へキシレングリコール等が挙げられる。
このような溶媒としては、例えば、ブチルセロソルブ、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、エチルカルビトール、ジアセトンアルコール、γ-ブチロラクトン、エチルラクテート、n-ヘキシルアセテート等が挙げられる。
また、電荷輸送性物質と電子受容性ドーパント物質の質量比も、発現する電荷輸送性、電荷輸送性物質等の種類を考慮して適宜設定されるものではあるが、通常、電荷輸送性物質1に対し、電子受容性ドーパント物質0~10、好ましくは0.1~3.0、より好ましくは0.2~2.0である。
そして、本発明において用いる正孔捕集層用組成物の粘度は、作製する薄膜の厚み等や固形分濃度を考慮し、塗布方法に応じて適宜調節されるものではあるが、通常25℃で0.1mPa・s~50mPa・s程度である。
なお、フッ素系界面活性剤、金属酸化物ナノ粒子等の添加順序も任意である。
塗布にあたっては、組成物の粘度と表面張力、所望する薄膜の厚さ等を考慮し、ドロップキャスト法、スピンコート法、ブレードコート法、ディップコート法、ロールコート法、バーコート法、ダイコート法、インクジェット法、印刷法(凸版、凹版、平版、スクリーン印刷等)等といった各種ウェットプロセス法の中から最適なものを採用すればよい。
また、通常、塗布は、常温、常圧の不活性ガス雰囲気下で行われるが、組成物中の化合物が分解したり、組成が大きく変化したりしない限り、大気雰囲気下(酸素存在下)で行ってもよく、加熱しながら行ってもよい。
(1)順積層型有機薄膜太陽電池
[陽極層の形成]:透明基板の表面に陽極材料の層を形成し、透明電極を製造する工程
陽極材料としては、インジウム錫酸化物(ITO)、インジウム亜鉛酸化物(IZO)等の無機酸化物や、金、銀、アルミニウム等の金属、ポリチオフェン誘導体、ポリアニリン誘導体等の高電荷輸送性有機化合物を用いることができる。これらの中ではITOが最も好ましい。また、透明基板としては、ガラスあるいは透明樹脂からなる基板を用いることができる。
陽極材料の層(陽極層)の形成方法は、陽極材料の性質に応じて適宜選択される。通常、難溶性、難分散性昇華性材料の場合には真空蒸着法やスパッタ法等のドライプロセスが選択され、溶液材料あるいは分散液材料の場合には、組成物の粘度と表面張力、所望する薄膜の厚さ等を考慮し、上述した各種ウェットプロセス法の中から最適なものが採用される。
ITO等の無機酸化物を陽極材料として用いて透明陽極基板を形成する場合、上層を積層する前に、洗剤、アルコール、純水等で洗浄してから使用することが好ましい。さらに、使用直前にUVオゾン処理、酸素-プラズマ処理等の表面処理を施すことが好ましい。陽極材料が有機物を主成分とする場合、表面処理を行わなくともよい。
上記方法に従い、陽極材料の層上に、本発明の組成物を用いて正孔捕集層を形成する。
活性層は、n型半導体材料からなる薄膜であるn層と、p型半導体材料からなる薄膜であるp層とを積層したものであっても、これら材料の混合物からなる非積層薄膜であってもよい。
なお、ここでいう「主鎖にチオフェン骨格」とはチオフェンのみからなる2価の芳香環、またはチエノチオフェン、ベンゾチオフェン、ジベンゾチオフェン、ベンゾジチオフェン、ナフトチオフェン、ナフトジチオフェン、アントラチオフェン、アントラジチオフェン等のような1以上のチオフェンを含む2価の縮合芳香環を表し、これらは上記R1~R6で示される置換基で置換されていてもよい。
必要に応じて、電荷の移動を効率化すること等を目的として、活性層と陰極層の間に電子捕集層を形成してもよい。
電子捕集層を形成する材料としては、酸化リチウム(Li2O)、酸化マグネシウム(MgO)、アルミナ(Al2O3)、フッ化リチウム(LiF)、フッ化ナトリウム(NaF)、フッ化マグネシウム(MgF2)、フッ化ストロンチウム(SrF2)、炭酸セシウム(Cs2CO3)、8-キノリノールリチウム塩(Liq)、8-キノリノールナトリウム塩(Naq)、バソクプロイン(BCP)、4,7-ジフェニル-1,10-フェナントロリン(BPhen)、ポリエチレンイミン(PEI)、エトキシ化ポリエチレンイミン(PEIE)等が挙げられる。
陰極材料としては、アルミニウム、マグネシウム-銀合金、アルミニウム-リチウム合金、リチウム、ナトリウム、カリウム、セシウム、カルシウム、バリウム、銀、金等の金属や、インジウム錫酸化物(ITO)、インジウム亜鉛酸化物(IZO)等の無機酸化物や、ポリチオフェン誘導体、ポリアニリン誘導体等の高電荷輸送性有機化合物が挙げられ、複数の陰極材料を積層したり、混合したりして使用することができる。
陰極層の形成方法も、上記と同様、陰極層材料が難溶性、難分散性昇華性材料の場合には上述した各種ドライプロセスが選択され、溶液材料あるいは分散液材料の場合には、組成物の粘度と表面張力、所望する薄膜の厚さ等を考慮し、上述した各種ウェットプロセス法の中から最適なものが採用される。
必要に応じて、光電流の整流性をコントロールすること等を目的として、任意の層間にキャリアブロック層を設けてもよい。キャリアブロック層を設ける場合、通常、活性層と、正孔捕集層または陽極との間に電子ブロック層を、活性層と、電子捕集層または陰極との間に正孔ブロック層を挿入する場合が多いが、この限りではない。
正孔ブロック層を形成する材料としては、酸化チタン、酸化亜鉛、酸化スズ、バソクプロイン(BCP)、4,7-ジフェニル1,10-フェナントロリン(BPhen)等が挙げられる。
電子ブロック層を形成する材料としては、N,N′-ジ(1-ナフチル)-N,N′-ジフェニルベンジジン(α-NPD)、ポリ(トリアリールアミン)(PTAA)等のトリアリールアミン系材料等が挙げられる。
[陰極層の形成]:透明基板の表面に陰極材料の層を形成し、透明陰極基板を製造する工程
陰極材料としては、上記順積層型の陽極材料で例示したものに加え、フッ素ドープ酸化錫(FTO)が挙げられ、透明基板としては、上記順積層型の陽極材料で例示したものが挙げられる。
陰極材料の層(陰極層)の形成方法も、難溶性、難分散性昇華性材料の場合には上述したドライプロセスが選択され、溶液材料あるいは分散液材料の場合には、組成物の粘度と表面張力、所望する薄膜の厚さ等を考慮し、上述した各種ウェットプロセス法の中から最適なものが採用される。
また、この場合も市販の透明陰極基板を好適に用いることができ、素子の歩留を向上させる観点からは、平滑化処理がされている基板を用いることが好ましい。市販の透明陰極基板を用いる場合、本発明の有機薄膜太陽電池の製造方法は、陰極層を形成する工程を含まない。
無機酸化物を陰極材料として使用して透明陰極基板を形成する場合、順積層型の陽極材料と同様の洗浄処理や、表面処理を施してもよい。
必要に応じて、電荷の移動を効率化すること等を目的として、活性層と陰極層の間に電子捕集層を形成してもよい。
電子捕集層を形成する材料としては、上記順積層型の材料で例示したものに加え、酸化亜鉛(ZnO)、酸化チタン(TiO)、酸化スズ(SnO)等が挙げられる。
電子捕集層の形成方法も、難溶性、難分散性昇華性材料の場合には上述したドライプロセスが選択され、溶液材料あるいは分散液材料の場合には、組成物の粘度と表面張力、所望する薄膜の厚さ等を考慮し、上述した各種ウェットプロセス法の中から最適なものが採用される。また、無機酸化物の前駆体層をウェットプロセス(特にスピンコート法かスリットコート法)を用いて陰極上に形成し、焼成して無機酸化物の層を形成する方法を採用することもできる。
活性層は、n型半導体材料からなる薄膜であるn層と、p型半導体材料からなる薄膜であるp層とを積層したものであっても、これら材料の混合物からなる非積層薄膜であってもよい。
n型およびp型半導体材料としては、上記順積層型の半導体材料で例示したものと同様のものが挙げられるが、n型材料としては、PC61BM、PC71BMが、p型材料としては、PTB7等の主鎖にチオフェン骨格を含むポリマー類が好ましい。
活性層の形成方法も、上記順積層型の活性層で説明した方法と同様である。
上記方法に従い、活性層材料の層上に、本発明の組成物を用いて正孔捕集層を形成する。
陽極材料としては、上記順積層型の陽極材料と同様のものが挙げられ、陽極層の形成方法としても、順積層型の陰極層と同様である。
順積層型の素子と同様、必要に応じて、光電流の整流性をコントロールすること等を目的として、任意の層間にキャリアブロック層を設けてもよい。
正孔ブロック層を形成する材料および電子ブロック層を形成する材料としては、上記と同様のものが挙げられ、キャリアブロック層の形成方法も上記と同様である。
封止法としては、端部にUV硬化樹脂を付着させた凹型ガラス基板を、不活性ガス雰囲気下、有機薄膜太陽電池素子の成膜面側に付着させ、UV照射によって樹脂を硬化させる方法や、真空下、スパッタリング等の手法によって膜封止タイプの封止を行う方法などが挙げられる。
(1)グローブボックス:山八物産(株)製、VACグローブボックスシステム
(2)蒸着装置:アオヤマエンジニアリング(株)製、真空蒸着装置
(3)ソーラーシミュレータ:分光計器(株)製、OTENTOSUN-III、AM1.5Gフィルター、放射強度:100mW/cm2
(4)ソースメジャーユニット:ケースレーインスツルメンツ(株)製、2612A
(5)膜厚測定装置:(株)小坂研究所製、サーフコーダ ET-4000
[調製例1]
PTB7(1-Material社製)20mgおよびPC61BM(フロンティアカーボン社製、製品名:nanom spectra E100)30mgが入ったサンプル瓶の中にクロロベンゼン2.0mLを加え、80℃のホットプレート上で15時間撹拌した。この溶液を室温まで放冷した後、1,8-ジヨードオクタン(東京化成工業(株)製)60μLを加えて撹拌し、溶液A1(活性層組成物)を得た。
[実施例1-1]
国際公開第2006/025342号の記載に基づいて合成した(以下、同様)上記式(2-1)で示されるアリールスルホン酸化合物A47.5mgを蒸留水3.16gに溶解し、aquaPASS-01X(三菱ケミカル(株)製,5.1質量%水溶液)1.86g、スノーテックスST-O(日産化学(株)製,20.4質量%水分散液)36.8mg、エタノール4.90gを加えて、濃度1.5質量%の茶褐色溶液を調製した。得られた茶褐色溶液に、フッ素系ノニオン性界面活性剤(FN-1287,第一工業製薬(株)製)を、茶褐色溶液全体に対して0.7質量%添加し、孔径0.45μmのシリンジフィルターでろ過して、正孔捕集層用組成物B1を得た。
上記式(2-1)で示されるアリールスルホン酸化合物A45.0mgを蒸留水3.25gに溶解し、aquaPASS-01X(三菱ケミカル(株)製,5.1質量%水溶液)1.77g、スノーテックスST-O(日産化学(株)製,20.4質量%水分散液)73.5mg、エタノール4.87gを加えて、濃度1.5質量%の茶褐色溶液を調製した。得られた茶褐色溶液に、フッ素系ノニオン性界面活性剤(FN-1287,第一工業製薬(株)製)を、茶褐色溶液全体に対して0.7質量%添加し、孔径0.45μmのシリンジフィルターでろ過して、正孔捕集層用組成物B2を得た。
上記式(2-1)で示されるアリールスルホン酸化合物A40.0mgを蒸留水3.44gに溶解し、aquaPASS-01X(三菱ケミカル(株)製,5.1質量%水溶液)1.57g、スノーテックスST-O(日産化学(株)製,20.4質量%水分散液)147mg、エタノール4.81gを加えて、濃度1.5質量%の茶褐色溶液を調製した。得られた茶褐色溶液に、フッ素系ノニオン性界面活性剤(FN-1287,第一工業製薬(株)製)を、茶褐色溶液全体に対して0.7質量%添加し、孔径0.45μmのシリンジフィルターでろ過して、正孔捕集層用組成物B3を得た。
上記式(2-1)で示されるアリールスルホン酸化合物A100mgを蒸留水6.13gに溶解し、aquaPASS-01X(三菱ケミカル(株)製,5.1質量%水溶液)3.92gとエタノール9.85gを加えて、濃度1.5質量%の濃青色溶液を調製した。得られた茶褐色溶液に、フッ素系ノニオン性界面活性剤(FN-1287,第一工業製薬(株)製)を、茶褐色溶液全体に対して0.7質量%添加し、孔径0.45μmのシリンジフィルターでろ過して、正孔捕集層用組成物C1を得た。
[実施例2-1]
20mm×20mmのITO透明導電層付ガラス基板を15分間UV/オゾン処理した。この基板に、電子捕集層となる酸化亜鉛の溶液(Genes’ Ink製)を滴下し、スピンコート法により成膜した。電子捕集層の膜厚は約20nmであった。その後、不活性ガスにより置換されたグローブボックス中で、形成した電子捕集層上に調製例1で得られた溶液A1を滴下してスピンコート法により成膜し、活性層を形成した。
次に、この活性層上に実施例1-1で調製した正孔捕集層用組成物B1をスピンコート法により塗布した後、ホットプレートを用いて60℃30分、さらに80℃10分のアニール処理することで正孔捕集層を形成した。正孔捕集層の膜厚は約50nmであった。
正孔捕集層用組成物B1の代わりに正孔捕集層用組成物B2を用いた以外は、実施例2-1と同様の方法で、密着性試験用の積層体を作製した。
正孔捕集層用組成物B1の代わりに正孔捕集層用組成物B3を用いた以外は、実施例2-1と同様の方法で、密着性試験用の積層体を作製した。
正孔捕集層用組成物B1の代わりに正孔捕集層用組成物C1を用いた以外は、実施例2-1と同様の方法で、密着性試験用の積層体を作製した。
上記実施例2-1~2-3および比較例2-1で作製した積層体について、剥離試験を行った。剥離試験はJIS K 5600-5-6に従って実施した。評価する膜に2mm感覚で6本の切込みを縦横に入れた後、18mm幅、付着強さ4N/cmのセロハンテープを膜面に貼り付け、約60°の方向に剥離を行った。剥離後の基板面とセロハンテープ面の付着度合いを目視で観察し、密着性の評価を行った。結果を表1に示す。
[実施例3-1]
陰極となるITO透明導電層を2mm×20mmのストライプ状にパターニングした20mm×20mmのガラス基板を15分間UV/オゾン処理した。この基板に、電子捕集層となる酸化亜鉛の溶液(Genes’ Ink製)を滴下し、スピンコート法により成膜した。電子捕集層の膜厚は約20nmであった。その後、不活性ガスにより置換されたグローブボックス中で、形成した電子捕集層上に調製例1で得られた溶液A1を滴下してスピンコート法により成膜し、活性層を形成した。
次に、この活性層上に実施例1-1で調製した正孔捕集層用組成物B1をスピンコート法により塗布した後、室温で乾燥させることで正孔捕集層を形成した。正孔捕集層の膜厚は約50nmであった。
最後に、積層した基板を真空蒸着装置内に設置して、装置内の真空度が1×10-3Pa以下になるまで排気し、抵抗加熱法によって、陽極となる銀層を80nmの厚さに蒸着することで、ストライプ状のITO層と銀層とが交差する部分の面積が2mm×2mmである逆積層型OPV素子を作製した。さらに、ホットプレートを用いて、60℃で30分間加熱してアニール処理を行った。
正孔捕集層用組成物B1の代わりに、正孔捕集層用組成物B2~B3を用いた以外は、実施例3-1と同様の方法で、逆積層型OPV素子を作製した。
上記実施例3-1~3-3で作製した各OPV素子について、短絡電流密度(Jsc〔mA/cm2〕)、開放電圧(Voc〔V〕)、曲線因子(FF)、およびPCE〔%〕の評価を行った。結果を表1に示す。
なおPCE〔%〕は、下式により算出した。
PCE〔%〕=Jsc〔mA/cm2〕×Voc〔V〕×FF÷入射光強度(100〔mW/cm2〕)×100
Claims (23)
- 式(1)で表されるポリアニリン誘導体からなる電荷輸送性物質と、フッ素系界面活性剤と、金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする有機光電変換素子の正孔捕集層用組成物。
mおよびnは、それぞれ、0≦m≦1、0≦n≦1、かつ、m+n=1を満たす数である。} - 前記金属酸化物ナノ粒子が、SiO2である請求項1記載の有機光電変換素子の正孔捕集層用組成物。
- 前記SiO2が、シリカゾルである請求項2記載の有機光電変換素子の正孔捕集層用組成物。
- 前記シリカゾルの分散媒が水である請求項3記載の有機光電変換素子の正孔捕集層用組成物。
- 前記フッ素系界面活性剤が、フッ素系ノニオン性界面活性剤である請求項1~4のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物。
- 前記R1が、スルホン酸基であり、前記R4が、炭素数1~20のアルコキシ基である請求項1~6のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物。
- 前記式(1)で表されるポリアニリン誘導体とは異なる電子受容性ドーパント物質を含む請求項1~7のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物。
- 前記電子受容性ドーパント物質が、ブレンステッド酸である請求項8記載の有機光電変換素子の正孔捕集層用組成物。
- 前記溶媒が、アルコール系溶媒および水から選ばれる1種または2種以上の溶媒を含む請求項1~10のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物。
- 前記有機光電変換素子が、有機薄膜太陽電池、色素増感太陽電池または光センサーである請求項1~11のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物。
- 請求項1~11のいずれか1項記載の有機光電変換素子の正孔捕集層用組成物を用いてなる正孔捕集層。
- 請求項13の正孔捕集層を有する有機光電変換素子。
- 請求項13の正孔捕集層と、それに接するように設けられた活性層とを有する有機光電変換素子。
- 前記活性層が、フラーレン誘導体を含む請求項14または15記載の有機光電変換素子。
- 前記活性層が、主鎖にチオフェンを含むポリマーを含む請求項14または15記載の有機光電変換素子。
- 前記活性層が、フラーレン誘導体および主鎖にチオフェン骨格を含むポリマーを含む請求項14または15記載の有機光電変換素子。
- 逆積層型である請求項14~18のいずれか1項記載の有機光電変換素子。
- 前記有機光電変換素子が、有機薄膜太陽電池、色素増感太陽電池または光センサーである請求項14~19のいずれか1項記載の有機光電変換素子。
- トップ陽極構造を有する請求項20記載の有機光電変換素子。
- 式(1)で表されるポリアニリン誘導体からなる電荷輸送性物質と、この式(1)で表されるポリアニリン誘導体とは異なる電子受容性ドーパント物質と、フッ素系界面活性剤と、金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする電荷輸送性組成物。
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JP7243636B2 (ja) | 2023-03-22 |
EP3726596A4 (en) | 2021-09-29 |
TWI791711B (zh) | 2023-02-11 |
EP3726596A1 (en) | 2020-10-21 |
CN111466038A (zh) | 2020-07-28 |
US11527719B2 (en) | 2022-12-13 |
US20200388762A1 (en) | 2020-12-10 |
JPWO2019116977A1 (ja) | 2020-12-17 |
BR112020011922A2 (pt) | 2020-11-24 |
KR20200100110A (ko) | 2020-08-25 |
TW201938684A (zh) | 2019-10-01 |
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