WO2021246351A1 - 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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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- ZQNWVCDSOIVSDI-UHFFFAOYSA-M lithium;8-hydroxyquinolin-2-olate Chemical compound [Li+].C1=C([O-])N=C2C(O)=CC=CC2=C1 ZQNWVCDSOIVSDI-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 125000001802 myricyl 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])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006606 n-butoxy 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
- 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 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
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 150000005087 tellurophenes Chemical class 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
- 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
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-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
- 238000001771 vacuum deposition 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/145—Side-chains containing sulfur
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
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- C—CHEMISTRY; METALLURGY
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- C08G2261/51—Charge transport
- C08G2261/516—Charge transport ion-conductive
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/79—Post-treatment doping
- C08G2261/794—Post-treatment doping with polymeric dopants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/94—Applications in sensors, e.g. biosensors
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/157—Hole transporting layers between the light-emitting layer and the cathode
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H—ELECTRICITY
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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 collecting layer of an organic photoelectric conversion element.
- An electronic element is a device that converts light energy into electrical 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 as an active layer or a charge transporting substance, and is an M.D.
- the organic thin-film solar cell developed by Tan is well known (Non-Patent Documents 1 and 2). Both are lightweight and thin films, can be made flexible, and can be produced roll-to-roll, which are different from the current mainstream inorganic solar cells, so they are new markets. The formation is expected.
- Non-Patent Document 3 organic thin-film solar cells have features such as electrolyte-free and heavy metal compound-free, and recently, a group of UCLA et al. Reported a photoelectric conversion efficiency (hereinafter abbreviated as PCE) of 10.6%. For this reason, it has received a great deal of attention (Non-Patent Document 3).
- organic thin-film solar cells show higher photoelectric conversion efficiency even in low light than existing photoelectric conversion elements using silicon-based materials, and the elements can be made thinner and the pixels can be miniaturized. Due to its features such as being able to combine the properties of a color filter, it is attracting attention not only for solar cell applications but also for optical sensor applications such as image sensors (Patent Documents 1 and 2 and Non-Patent Documents 4). ).
- organic solar cells die-sensitized solar cells and organic thin-film solar cells
- they are collectively referred to as organic photoelectric conversion elements (hereinafter, may be abbreviated as OPV) including applications such as optical sensors.
- the organic photoelectric conversion element is configured to include an active layer (photoelectric conversion layer), a charge (hole, electron) collecting layer, an electrode (anode, cathode) and the like.
- the active layer and the charge collection layer are generally formed by the vacuum vapor deposition method, but the vacuum vapor deposition method has problems in terms of complexity due to mass production process, high cost of equipment, efficiency of material utilization, and the like. There is.
- a water-dispersible polymer organic conductive material such as PEDOT / PSS may be used as a coating material for the hole collecting layer, but the PEDOT / PSS water dispersion liquid has a solid content.
- PEDOT / PSS water dispersion liquid has a solid content.
- the present invention has been made in view of the above circumstances, and provides a composition for a hole collecting layer of an organic photoelectric conversion element, which provides a hole collecting layer having excellent adhesion to an active layer.
- the purpose is to provide a composition for a hole collecting layer of an organic photoelectric conversion element, which provides a hole collecting layer having excellent adhesion to an active layer.
- the present inventors have already reported a composition containing a predetermined polythiophene as a charge-transporting substance as a composition for a hole collecting layer that can achieve the above object (see Patent Document 3).
- the metal oxide nanoparticles are indispensable as the adhesion-imparting component in this composition, it is good for the active layer even if the adhesion-imparting component is not contained or the content thereof is small. It is desired to develop a composition that exhibits a good adhesion.
- the present inventors refer to a composition that gives a thin film having excellent adhesion to the active layer without adding an adhesion-imparting component such as metal oxide nanoparticles as a polythiophene structure.
- the cyclic ethylenedioxy group has a structure in which a cyclic ethylenedioxy group is fused to the thiophene ring, and further binds to the cyclic ethylenedioxy group.
- Polythiophene derivatives having a predetermined side chain containing sulfonic acid or sulfonic acid base can form a uniform solution showing high solubility in protonic polar solvents such as alcohol and water, which are less corrosive to the active layer.
- the thin film prepared from this solution not only exhibits high hole transportability, but also when the thin film is used as an OPV hole collecting layer, it is an active layer without using other adhesion-imparting components.
- the present invention has been completed by finding that an OPV showing good PCE can be obtained by exhibiting good adhesion to the above.
- the present invention provides a composition for a hole collecting layer of the following organic photoelectric conversion element.
- 1. A composition for a hole collecting layer of an organic photoelectric conversion element containing a charge transporting substance composed of a polythiophene derivative containing a repeating unit represented by the formula (1) or the formula (1') and a solvent.
- R 1 represents an alkyl group having 1 to 6 carbon atoms or a fluorine atom.
- M is a hydrogen atom, Li, Na and K.
- R 2 may have hydrogen atoms or substituents independently of each other and may have 1 to 6 carbon atoms. Represents an alkyl group.) 2. 2. Further, a composition for a hole collecting layer of 1 organic photoelectric conversion element containing a surfactant. 3. 3. The composition for a hole collecting layer of the organic photoelectric conversion element 2 in which the above-mentioned surfactant is a fluorine-based surfactant. 4. Further, the hole collecting layer of any of the organic photoelectric conversion elements 1 to 3 containing an electron-accepting dopant substance different from the polythiophene derivative containing the repeating unit represented by the above formula (1) or the formula (1'). Composition for. 5.
- the electron-accepting dopant substance different from the polythiophene derivative containing the repeating unit represented by the above formula (1) or the formula (1') is for the hole collecting layer of the organic photoelectric conversion element 4 which is an aryl sulfonic acid compound.
- Composition. 6. A hole collecting layer obtained from the composition for a hole collecting layer of any of the organic photoelectric conversion elements 1 to 5. 7. An organic photoelectric conversion element including a hole collecting layer of 6.
- the composition for the hole collecting layer of the organic photoelectric conversion element of the present invention contains a predetermined polythiophene derivative, the hole collecting layer obtained from the composition has good adhesion to the active layer. As a result, an organic thin-film solar cell having excellent PCE can be obtained.
- composition for a hole collecting layer of the present invention contains a charge-transporting substance composed of a polythiophene derivative containing a repeating unit represented by the formula (1) or the formula (1'), and a solvent.
- R 1 represents an alkyl group having 1 to 6 carbon atoms or a fluorine atom.
- M represents an alkali metal selected from the group consisting of hydrogen atom, Li, Na and K, NH (R 2 ) 3 or HNC 5 H 5 .
- R 2 represents an alkyl group having 1 to 6 carbon atoms, which may have a hydrogen atom or a substituent independently of each other.
- the alkyl group having 1 to 6 carbon atoms may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, isobutyl and sec-. Examples thereof include butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, n-hexyl, 2-ethylbutyl, cyclohexyl, n-octyl group and the like.
- R 1 a linear or branched alkyl group having 1 to 3 carbon atoms is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is even more preferable.
- the alkyl group having 1 to 6 carbon atoms of R 2 the same one as that of R 1 can be exemplified.
- the substituent includes, for example, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 20 carbon atoms. Examples thereof include a hydroxy group, an amino group and a carboxy group.
- Examples of the alkyl group having 1 to 6 carbon atoms include the same groups as those exemplified in R 1 above, and examples of the alkoxy group having 1 to 6 carbon atoms include methoxy, ethoxy, n-propoxy, i-propoxy, and the like.
- Examples of the aryl group having 6 to 20 carbon atoms include phenyl, tolyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl and 2-phenanthryl. , 3-Phenyltril, 4-Phenyltril, 9-Phenyltril group and the like.
- the substituent is preferably a hydroxy group
- examples of the alkyl group having a hydroxy group include a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 2,3-dihydroxypropyl group and the like.
- R 2 a hydrogen atom and a linear or branched alkyl group having 1 to 3 carbon atoms are preferable, and a hydrogen atom and a methyl group are more preferable.
- polythiophene derivative containing the repeating unit represented by the above formula (1) as a preferred embodiment, for example, polythiophene containing the repeating unit represented by the following formula (1-1) can be mentioned.
- polythiophene derivative are at least one of the repeating units represented by the following formulas (1-1-A) to (1-1-B) and formulas (1'-A) to (1'-B).
- Polythiophene including.
- the polythiophene derivative may be a homopolymer or a copolymer (including statistical, random, gradient, and block copolymers).
- block copolymers include, for example, AB diblock copolymers, ABA triblock copolymers, and (AB) m -multiblock copolymers.
- the polythiophene derivative is derived from other types of monomers such as thienothiophene, selenophene, pyrrole, furan, tellurophenes, aniline, arylamine, and arylene (eg, phenylene, phenylenebinylene, and fluorene). May include repeating units.
- the content of the repeating unit represented by the formula (1) or the formula (1') in the polythiophene derivative is preferably more than 50 mol%, preferably 80 mol% or more, among all the repeating units contained in the polythiophene derivative. More preferably, 90 mol% or more is further preferable, 95 mol% or more is further preferable, and 100 mol% is most preferable.
- the polymer formed may contain repeating units derived from impurities.
- the term "homomopolymer” above means a polymer comprising repeating units derived from one type of monomer, but may also contain repeating units derived from impurities. ..
- the polythiophene derivative is preferably a homopolymer in which basically all the repeating units are the repeating units represented by the above formula (1), and the repeating units represented by the above formula (1-1). A certain homopolymer is more preferable, and a homopolymer which is any repeating unit represented by the above formulas (1-1-A) to (1-1-B) is even more preferable.
- a polythiophene derivative containing the repeating unit represented by the above formula (1) or the formula (1') used in the present invention a polythiophene derivative produced by a conventionally known method may be used, or a commercially available product may be used.
- known methods include the methods described in JP-A-2014-65598, which are polymerized in the presence of an oxidizing agent in water or an alcohol solvent using a thiophene monomer as shown below as a raw material. Can be manufactured.
- examples of commercially available products include SELFTRON S and SELFTRON H (both manufactured by Tosoh Corporation) of the SELFTRON (registered trademark) series.
- thiophene monomers examples include 3-[(2,3-dihydrothieno [3,4-b]-[1,4] dioxin-2-yl) methoxy] -1-methyl-1-sodium propanesulfonate.
- the weight average molecular weight of the polythiophene derivative containing the repeating unit represented by the formula (1) or the formula (1') is not particularly limited, but is usually about 1,000 to 1,000,000 in terms of polystyrene sulfonic acid. Is preferable, and about 1,000 to 200,000 is more preferable for the use of the water-soluble conductive polymer. When the weight average molecular weight is set to the lower limit or more, good conductivity is obtained, and when the weight average molecular weight is set to the upper limit or lower, the solubility in a solvent is improved.
- the weight average molecular weight is a polystyrene sulfonic acid conversion value obtained by gel permeation chromatography.
- the polythiophene derivative containing the repeating unit represented by the formula (1) or the formula (1') may be used alone or in combination of two or more compounds. ..
- 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 even 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 hole collecting layer obtained by using the composition.
- the electron-accepting dopant substance is not particularly limited as long as it is soluble in at least one solvent used.
- the electron-accepting dopant substance include inorganic strong acids such as hydrogen chloride, sulfuric acid, nitric acid, and phosphoric acid; aluminum chloride (III) (AlCl 3 ), titanium tetrachloride (IV) (TiCl 4 ), and boron tribromide.
- BBr 3 Borone Trifluorinated Ether Complex (BF 3 ⁇ OEt 2 ), Iron Chloride (III) (FeCl 3 ), Copper Chloride (II) (CuCl 2 ), Antimonium Prefide (V) (SbCl 5 ), Lewis acids such as arsenic pentoxide (V) (AsF 5 ), phosphorus pentoxide (PF 5 ), tris (4-bromophenyl) aluminum hexachloroantimonate (TBPAH); benzenesulfonic acid, tosylic acid, hydroxybenzenesulfon Acid, 5-sulfosalicylic acid, dodecylbenzene sulfonic acid, polystyrene sulfonic acid, 1,4-benzodioxane disulfonic acid compound described in International Publication No.
- Naphthalene sulfonic acid compounds aryl sulfonic acid compounds such as dinonylnaphthalene sulfonic acid and 1,3,6-naphthalentrisulfonic acid described in JP-A-2005-108828, and organic strong acids such as camphorsulfonic acid; polystyrene.
- Sulfonates such as sodium sulfonate; 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), iodine and the like
- TCNQ 7,7,8,8-tetracyanoquinodimethane
- DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
- iodine and the like examples thereof include organic oxidizing agents and inorganic oxidizing agents such as heteropolyacid compounds such as phosphomolybdic acid, phosphotungnic acid and lintangustomolydic acid described in International Publication No. 2010/0587777, and these may be used alone. Two or more kinds may be used in combination.
- Bronsted acid that donates H + is particularly preferable, aryl sulfonic acid compound is more preferable, and polystyrene sulfonic acid and aryl represented by the following formula (2) are particularly preferable. Sulfonic acid compounds are preferred.
- X represents O
- A represents a naphthalene ring or an anthracene ring
- B represents a 2- to tetravalent perfluorobiphenyl group
- l represents the number of sulfonic acid groups attached to A. It is an integer satisfying 1 ⁇ l ⁇ 4, and q indicates the number of bonds between B and X, and is an integer satisfying 2 to 4.
- aryl sulfonic acid compound examples include the following compounds (formula (2-1)).
- the composition of the present invention may contain a surfactant from the viewpoint of film forming property.
- the surfactant is not particularly limited, and a fluorine-based surfactant, a silicone-based surfactant, or the like can be used, but in the present invention, it is preferable to use a fluorine-based surfactant.
- the fluorine-based surfactant used in the present invention is available as a commercially available product.
- Such commercially available products include DuPont Capstone (Captone, registered trademark) FS-10, FS-22, FS-30, FS-31, FS-34, FS-35, FS-50, FS-51, etc.
- Examples thereof include Megafuck F-444, F-477, F-559 manufactured by Megafuck Co., Ltd., but the present invention is not limited thereto.
- Capstone FS-30, 31, 34, 35, 3100, Neugen FN-1287, and Megafuck F-559 which are nonionic surfactants, are suitable.
- the fluorine-based surfactant is not particularly limited as long as it contains a fluorine atom, and may be cationic, anionic, or nonionic, but a fluorine-based nonionic surfactant is preferable.
- a fluorine-based 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, a heteroaryl group having 2 to 20 carbon atoms and the like.
- the alkyl group having 1 to 40 carbon atoms may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and s-butyl.
- aralkyl group having 7 to 20 carbon atoms include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl and 2-propylphenyl.
- examples thereof include methyl, 4-isopropylphenylmethyl, 4-isobutylphenylmethyl, ⁇ -naphthylmethyl group and the like.
- heteroaryl group examples include 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isooxazolyl, 4-isoxazolyl, 5-isooxazolyl, 2 -Thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl, 3-pyrazyl , 5-Pyradil, 6-Pyramidyl, 2-Pyrimidyl, 4-Pyrimidyl, 5-Pyrimidil, 6-Pyramidil, 3-Pyridadyl, 4-Pyridadil, 5-Pyridadil, 6-Pyridadil, 1,2,3-Tria
- 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.
- the perfluoroalkyl polyoxyethylene ester represented by (A2) below and the perfluoroalkyl polyoxyethylene ether or fluorine telomer alcohol represented by (B2) having a perfluoroalkyl group R f having 1 to 40 carbon atoms are shown below. At least one fluorine-based nonionic surfactant selected from the above is more preferable.
- n has the same meaning as above.
- perfluoroalkyl group having 1 to 40 carbon atoms include a group in which all the hydrogen atoms of the alkyl group having 1 to 40 carbon atoms are replaced with fluorine atoms.
- the content of the surfactant is not particularly limited, but the improvement of the film-forming property on the active layer, the adhesion to the active layer by addition, and the photoelectric conversion of the obtained element are performed. Considering the balance with the decrease in efficiency, about 0.005 to 0.08% by mass of the whole composition is preferable, 0.005 to 0.05% by mass is more preferable, and 0.005 to 0.04% by mass is more preferable. Even more preferably, 0.0075 to 0.03% by mass is further preferable, and 0.01 to 0.02% by mass is most preferable.
- composition of the present invention contains the polythiophene derivative represented by the above-mentioned formula (1), it provides a thin film that exhibits sufficient adhesion to the active layer even if it does not contain metal oxide nanoparticles.
- metal oxide nanoparticles may be contained. Nanoparticles mean fine particles having an average particle size on the order of nanometers (typically 500 nm or less) for primary particles.
- the metal oxide nanoparticles mean metal oxides formed into nanoparticles.
- the primary particle size of the metal oxide nanoparticles used in the present invention is not particularly limited as long as it is nano-sized, but 2 to 150 nm is preferable, and 3 to 150 nm is preferable 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.
- the particle size is a measured value using a nitrogen adsorption isotherm by the BET method.
- the metal constituting the metal oxide nanoparticles in the present invention includes not only metals in the usual sense but also metalloids.
- the metal in the usual sense 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 W (tungsten).
- Metalloids on the other hand, mean elements whose chemical and / or physical properties are between metal and non-metal.
- metalloids Although the universal definition of metalloids has not been established, in the present invention, a total of 6 of boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb) and tellurium (Te).
- B boron
- Si silicon
- Ge germanium
- As arsenic
- Sb antimony
- Te tellurium
- the element is a metalloid.
- These metalloids may be used alone, in combination of two or more, or in combination with a metal in the usual sense.
- the metal oxide nanoparticles used in the present invention include boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te), tin (Sn), and titanium (Ti). , Aluminum (Al), Zirconium (Zr), Zinc (Zn), Niobium (Nb), Tantalum (Ta) and W (Tungsten), preferably containing oxides of one or more metals.
- the metal oxide may be a mixture of individual metal oxides or a composite 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 , and Sb 2.
- Examples include O 5 , TeO 2 , SnO 2 , ZrO 2 , Al 2 O 3 , ZnO, etc., but 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, with SiO 2 being more preferred.
- the metal oxide nanoparticles may contain 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 content thereof is not particularly limited, but from the viewpoint of fully exerting the advantages of the present invention, 50 parts by mass of the charge transporting substance is used. Less than parts by mass is preferable, 30 parts by mass or less is more preferable, and 10 parts by mass or less is even more preferable.
- the charge-transporting substance is used as a solution or a dispersion, the amount of the metal oxide nanoparticles added is based on the solid content of the charge-transporting substance.
- the metal oxide nanoparticles it is preferable to use as the metal oxide nanoparticles a silica sol in which SiO 2 nanoparticles are dispersed in a dispersion medium.
- the silica sol is not particularly limited, and a known silica sol can be appropriately selected and used. Commercially available silica sol is usually in the form of a dispersion.
- SiO 2 nanoparticles are used in various solvents such as water, methanol, methyl ethyl ketone, methyl isobutyl ketone, N, N-dimethylacetamide, ethylene glycol, isopropanol, methanol, ethylene glycol monopropyl ether, cyclohexanone, and acetate.
- solvents such as water, methanol, methyl ethyl ketone, methyl isobutyl ketone, N, N-dimethylacetamide, ethylene glycol, isopropanol, methanol, ethylene glycol monopropyl ether, cyclohexanone, and acetate.
- solvents such as water, methanol, methyl ethyl ketone, methyl isobutyl ketone, N, N-dimethylacetamide, ethylene glycol, isopropanol, methanol, ethylene glycol monopropyl ether, cyclo
- 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 an alcohol solvent is more preferable.
- the alcohol solvent a water-soluble alcohol is preferable, and methanol, 2-propanol, and ethylene glycol are more preferable.
- silica sol examples include Snowtex (registered trademark) ST-O, ST-OS, ST-O-40, ST-OL manufactured by Nissan Chemical Industries, Ltd., and silica doll 20 manufactured by Nippon Chemical Industrial Co., Ltd. , 30, 40, etc.
- the solid content concentration of the silica sol is also not particularly limited, but is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and even more preferably 15 to 30% by mass.
- the content is preferably less than 50 parts by mass, more preferably 30 parts by mass or less, still more preferably 10 parts by mass or less, based on 100 parts by mass of the charge-transporting substance, as described above. preferable.
- the blending amount is also based on the solid content of the charge transporting substance as described above.
- the composition of the present invention may contain alkoxysilane.
- alkoxysilane By including alkoxysilane, the solvent resistance and water resistance of the obtained thin film can be improved, the electron blocking property can be improved, and the HOMO level and LUMO level can be set to optimum values for the active layer.
- the alkoxysilane may be a siloxane-based material.
- any one or more alkoxysilanes can be used from among tetraalkoxysilane, trialkoxysilane, and dialkoxysilane, and in particular, tetraethoxysilane, tetramethoxysilane, phenyltriethoxysilane, and phenyltri.
- siloxane-based material include polysiloxanes such as poly (tetraethoxysilane) and poly (phenylethoxysilane) obtained by a reaction such as hydrolysis with the above alkoxysilane.
- the amount of alkoxysilane added is not particularly limited as long as it exhibits the above effects, but is preferably 0.0001 to 100 times by mass ratio with respect to the polythiophene derivative used in the present invention, and is 0.01 to 50 times. Double is more preferable, and 0.05 to 10 times is even more preferable.
- composition for a hole collecting layer of the present invention may further contain a matrix polymer, if necessary.
- matrix polymer include a matrix polymer containing a repeating unit represented by the following formula (I) and a repeating unit represented by the following formula (II).
- R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independent of each other and have a hydrogen atom, a halogen atom, a fluoroalkyl group having 1 to 20 carbon atoms, or a carbon number of carbon atoms. It is a perfluoroalkyl group of 1 to 20, and Q is-[OC (R h R i ) -C (R j R k )] y- O- [CR l R m ] z -SO 3 H.
- R h , R i , R j , R k , R l and R m are independent of each other, a hydrogen atom, a halogen atom, a fluoroalkyl group having 1 to 20 carbon atoms, or a perfluoroalkyl group having 1 to 20 carbon atoms. It is an atom, y is 0 to 10, and z is 1 to 5.
- fluoroalkyl group having 1 to 20 carbon atoms and the perfluoroalkyl group having 1 to 20 carbon atoms include the same as above.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- R 3 , R 4 , R 5 and R 6 are fluorine atoms or chlorine atoms, R 3 , R 5 and R 6 are fluorine atoms, and R 4 is a chlorine atom. Is more preferable, and it is even more preferable that R 3 , R 4 , R 5 and R 6 are all fluorine atoms.
- R 7 , R 8 and R 9 are all fluorine atoms.
- R h , R i , R j , R k , R l and R m are a fluorine atom, a fluoroalkyl group having 1 to 8 carbon atoms, or a perfluoroalkyl group having 1 to 8 carbon atoms.
- R l and R m are fluorine atoms. Further, y is preferably 0, and z is preferably 2.
- R 3 , R 5 , and R 6 above are fluorine atoms
- R 4 is a chlorine atom
- R l and R m are fluorine atoms
- y is 0
- And z is preferably 2.
- each R 3 , R 4 , R 5 , and R 6 is a fluorine atom; and each R l and R m is a fluorine atom; y is 0; And z is preferably 2.
- the ratio (s: t ratio) between the number "s" of the repeating units represented by the formula (I) and the number "t” of the repeating units represented by the formula (II) is not particularly limited.
- the s: t ratio is preferably 9: 1 to 1: 9, more preferably 8: 2 to 2: 8.
- the matrix polymer that can be suitably used in the present invention, one synthesized by a known method or a commercially available product may be used.
- the polymer containing the repeating unit represented by the above formula (I) and the repeating unit represented by the above formula (II) is represented by the monomer represented by the following formula (Ia) and the following formula (IIa). It can be produced by copolymerizing with a monomer by a known polymerization method and then converting it into a sulfonic acid group by hydrolysis of a sulfonylfluoride group.
- Q 1 is ⁇ [OC (R h R i ) ⁇ C (R j R k )] y ⁇ O ⁇ [CR l R m ] z ⁇ SO 2 F, and is R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R h , R i , R j , R k , R l , R m , y and z have the same meanings as above.
- TFE tetrafluoroethylene
- CTFE chlorotrifluoroethylene
- F 2 C CF-O -CF 2 -CF 2 - SO 2 F
- F 2 C CF- [O-CF 2 -CR 12 F-O] y -CF 2 -CF 2 -SO 2 F ( where
- the equivalent of the matrix polymer means the mass (g / mol) of the matrix polymer per mol of the acid group present in the matrix polymer.
- the equivalent of the matrix polymer is preferably about 400 to about 15,000 g / mol, more preferably about 500 to about 10,000 g / mol, even more preferably about 500 to about 8,000 g / mol, still more preferably about. It is 500 to about 2,000 g / mol, most preferably about 600 to about 1,700 g / mol.
- Such matrix polymers are available as commercial products.
- Examples of commercially available products include Nafion (NAFION, registered trademark) manufactured by DuPont, AQUIVION (AQUIVION, registered trademark) manufactured by Solvay Specialty Polymers, and Flemion (FLEMION, registered trademark) manufactured by Asahi Glass Co., Ltd.
- the matrix polymer is preferably a polyether sulfone containing one or more repeating units containing at least one sulfonic acid residue (-SO 3 H).
- additives may be added to the composition of the present invention as long as the object of the present invention can be achieved.
- type of additive a known one can be appropriately selected and used according to a desired effect.
- the solvent used for preparing the composition for the hole collecting layer a polythiophene derivative and, if necessary, a highly soluble solvent capable of satisfactorily dissolving the electron-accepting dopant substance used can be used.
- the highly soluble solvent can be used alone or in combination of two or more, and the amount used may be 5 to 100% by mass based on the total amount of the solvent used in the composition.
- Examples of such a highly soluble solvent include water; an alcohol solvent such as ethanol, 2-propanol, 1-butanol, 2-butanol, s-butanol, t-butanol, 1-methoxy-2-propanol, and N.
- an alcohol solvent such as ethanol, 2-propanol, 1-butanol, 2-butanol, s-butanol, t-butanol, 1-methoxy-2-propanol, and N.
- organic solvents such as solvents. Among these, 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 more kinds of solvents selected from alcohol-based solvents and water, which does not adversely affect the active layer, is used. It is preferable to use it.
- the charge-transporting substance and the electron-accepting dopant substance used as needed are preferably completely dissolved in the above solvent or uniformly dispersed, and are organic with high conversion efficiency. Considering that the hole collecting layer that gives the thin film solar cell can be obtained with good reproducibility, it is more preferable that these substances are completely dissolved in the above solvent.
- the composition for a hole collecting 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 the film forming property and the ejection property from the coating apparatus.
- At least one kind of high-viscosity organic solvent having a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure may be contained.
- the high-viscosity organic solvent is not particularly limited, and is, for example, cyclohexanol, ethylene glycol, 1,3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, 1,3-butane. Examples thereof include diol, 2,3-butanediol, 1,4-butanediol, propylene glycol, hexylene glycol and the like.
- the addition ratio of the high-viscosity organic solvent to the entire solvent used in the composition of the present invention is preferably within 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. It is preferable to have.
- the composition for the purpose of improving the wettability with respect to the coated surface, adjusting the surface tension of the solvent, adjusting the polarity, adjusting the boiling point, etc., another solvent that can impart the flatness of the film during heat treatment is used in the composition. It is also possible to mix in a ratio of 1 to 90% by mass, preferably 1 to 50% by mass with respect to the whole.
- Examples of such a solvent include 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, and ethyl carbitol.
- Examples thereof include diacetone alcohol, ⁇ -butylolactone, ethyl lactate, n-hexyl acetate and the like.
- 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, and the like, but is usually 0.1 to 10.0 mass. It is about%, preferably 0.5 to 5.0% by mass, and more preferably 1.0 to 3.0% by mass. Further, the mass ratio of the charge-transporting substance and the electron-accepting dopant substance is also appropriately set in consideration of the types of the charge-transporting substance, the 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, and more preferably 0.2 to 2.0.
- the viscosity of the composition for the hole collecting layer used in the present invention is appropriately adjusted according to the coating method in consideration of the thickness of the thin film to be produced and the solid content concentration, but is usually at 25 ° C. It is about 0.1 to 50 mPa ⁇ s.
- the composition for the hole collecting layer of the present invention when preparing the composition for the hole collecting layer of the present invention, as long as the solid content is uniformly dissolved or dispersed in the solvent, the charge transporting substance and the solvent, and the fluorine-based surfactant and the metal used as necessary are necessary.
- the oxide nanoparticles, the electron-accepting dopant substance, and the like can be mixed in any order.
- a method of dissolving a polythiophene derivative in a solvent and then dissolving an electron-accepting dopant substance in the solution a method of dissolving an electron-accepting dopant substance in a solvent and then dissolving the polythiophene derivative in the solution
- Any method of mixing a polythiophene derivative and an electron-accepting dopant substance and then adding the mixture to a solvent to dissolve the mixture can be adopted as long as the solid content is uniformly dissolved or dispersed in the solvent.
- the order of adding the matrix polymer and the alkoxysilane is also arbitrary.
- the composition is prepared in an inert gas atmosphere at room temperature and normal pressure, but unless the compound in the composition is decomposed or the composition is significantly changed, the composition is prepared in an atmospheric atmosphere (oxygen presence). It may be carried out in (below), or it may be carried out while heating.
- the composition described above is applied on an anode in the case of a forward-laminated organic thin-film solar cell and on an active layer in the case of a reverse-laminated organic thin-film solar cell and fired to collect holes of the present invention.
- Layers can be formed.
- the drop casting method, spin coating method, blade coating method, dip coating method, roll coating method, bar coating method, die coating method, etc. are taken into consideration in consideration of the viscosity and surface tension of the composition, the desired thin film thickness, etc.
- the most suitable wet process method may be adopted from various wet process methods such as an inkjet method, a printing method (letter plate, concave plate, lithographic plate, screen printing, etc.).
- the coating is usually carried out in an inert gas atmosphere at normal temperature and pressure, but in an air atmosphere (in the presence of oxygen) unless the compound in the composition is decomposed or the composition is significantly changed. You may go or you may go while 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 a method of changing the solid content concentration in the composition, a method of changing the amount of the solution at the time of coating, and the like.
- Forward-laminated organic thin-film solar cell A process of forming a layer of an anode material on the surface of a transparent substrate to manufacture a transparent electrode.
- the anode material include indium tin oxide (ITO) and 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. Of these, ITO is the most preferable.
- the transparent substrate a substrate made of glass or a transparent resin can be used.
- the method for forming the layer of the anode material is appropriately selected depending on the properties of the anode material.
- a dry process such as a vacuum deposition method or a sputtering method is selected in the case of a poorly soluble or poorly dispersible sublimable material, and in the case of a solution material or a dispersion liquid material, the viscosity and surface tension of the composition are desired.
- the thickness of the thin film and the like the most suitable one is adopted from the various wet process methods described above.
- a commercially available transparent anode substrate can also be used. In this case, from the viewpoint of improving the yield of the device, it is preferable to use a substrate that has been smoothed.
- the method for manufacturing an organic thin-film solar cell of the present invention does not include a step of forming an anode layer.
- a transparent anode substrate is formed by using an inorganic oxide such as ITO as an anode material, it is preferable to wash the transparent anode substrate with a detergent, alcohol, pure water or the like before laminating the upper layer. Further, it is preferable to perform surface treatment such as UV ozone treatment and oxygen-plasma treatment immediately before use.
- the anode material contains an organic substance as a main component, it is not necessary to perform surface treatment.
- Step of forming a hole collecting layer on the formed layer of the anode material Step of forming a hole collecting layer on the formed layer of the anode material
- the composition of the present invention is used to capture holes on the layer of the anode material. Form a layer.
- the active layer is a thin film made of an n-type semiconductor material and a thin film made of a p-type semiconductor material. It may be a laminated thin film or a non-laminated thin film made of a mixture of these materials.
- n-type semiconductor material examples include fullerene, [6,6] -phenyl-C 61- methyl butyrate (PC 61 BM), [6,6] -phenyl-C 71- methyl butyrate (PC 71 BM), and the like. Can be mentioned.
- examples of the p-type semiconductor material are described in Regular Poly (3-hexylthiophene) (P3HT), PTB7 represented by the following formula (3), JP-A-2009-158921, and International Publication No. 2010/008672.
- Examples thereof include polymers containing a thiophene skeleton in the main chain, phthalocyanines such as CuPC and ZnPC, and porphyrins such as tetrabenzoporphyrin, such as polymers containing thienothiophene units.
- n-type material PC 61 BM and PC 71 BM are preferable
- p-type material polymers having a thiophene skeleton in the main chain such as PTB7 are preferable.
- the "thiophene skeleton in the main chain" here is a divalent aromatic ring consisting of only thiophene, or thienothiophene, benzothiophene, dibenzothiophene, benzodithiophene, naphthophene, naphthodithiophene, anthrathiophene, anthrazi.
- thiophenes such as thiophene, which are a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms.
- Thioalkoxy group alkyl group with 1 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, alkynyl group with 2 to 20 carbon atoms, haloalkyl group with 1 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, carbon It may be substituted with an aralkyl group having a number of 7 to 20 or an acyl group having 1 to 20 carbon atoms.
- halogen atom examples include the same as those exemplified above.
- the alkoxy group having 1 to 20 carbon atoms may be linear, branched or cyclic in that of the alkyl group, and may be methoxy, ethoxy, n-propoxy, i-propoxy, c-propoxy or n-butoxy.
- I-butoxy, s-butoxy, t-butoxy, n-pentoxy, n-hexoxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy examples thereof include n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-nonadecyloxy, n-eicosanyloxy group and the like. ..
- thioalkoxy group having 1 to 20 carbon atoms include a group in which the oxygen atom of the alkoxy group is replaced with a sulfur atom.
- examples of the thioalkoxy (alkylthio) group having 1 to 20 carbon atoms include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, t-butylthio, n-pentylthio, n-hexylthio and n.
- alkenyl group having 2 to 20 carbon atoms examples include ethenyl, n-1-propenyl, n-2-propenyl, 1-methylethenyl, n-1-butenyl, n-2-butenyl, n-3-butenyl and 2-methyl.
- -1-propenyl, 2-methyl-2-propenyl, 1-ethylethenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, n-1-pentenyl, n-1-decenyl, n-1-eicosenyl Group etc. can be mentioned.
- alkynyl group having 2 to 20 carbon atoms examples include ethynyl, n-1-propynyl, n-2-propynyl, n-1-butynyl, n-2-butynyl, n-3-butynyl and 1-methyl-2-propynyl.
- haloalkyl group having 1 to 20 carbon atoms examples include a group in which at least one of the hydrogen atoms in the alkyl group is replaced with a halogen atom.
- the halogen atom may be any of chlorine, bromine, iodine and fluorine atoms. Of these, a fluoroalkyl group is preferable, and a perfluoroalkyl group is more preferable.
- acyl group having 1 to 20 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, benzoyl group and the like.
- the method for forming the active layer similarly to the above, when the active layer material is a sparingly soluble sublimation material, the above-mentioned various dry processes are selected, and when the active layer material is a solution material or a dispersion liquid material, the viscosity and surface of the composition are selected. Considering the tension, the desired thickness of the thin film, etc., the most suitable one is adopted from the various wet process methods described above.
- Step of forming an electron collecting layer on the formed active layer If necessary, for the purpose of improving the efficiency of charge transfer, etc., between the active layer and the cathode layer.
- An electron collecting layer may be formed.
- Materials for forming the electron collection layer include lithium oxide (Li 2 O), magnesium oxide (MgO), alumina (Al 2 O 3 ), lithium fluoride (LiF), sodium fluoride (NaF), and magnesium fluoride.
- the method for forming the electron collecting layer similarly to the above, when the electron collecting material is a sparingly soluble sublimation material, the above-mentioned various dry processes are selected, and when the electron collecting material is a solution material or a dispersion liquid material, the composition. Considering the viscosity, surface tension, desired thin film thickness, etc., the most suitable wet process method described above is adopted.
- Step of forming a cathode layer on the formed electron collection layer examples include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium, and calcium. Examples thereof include 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. Can be used by laminating or mixing the cathode materials of.
- the above-mentioned various dry processes are selected when the cathode layer material is a poorly soluble or poorly dispersible sublimable material, and when the cathode layer material is a solution material or a dispersion liquid material, a composition is selected.
- the optimum one is adopted from the various wet process methods described above in consideration of the viscosity and surface tension of the above-mentioned material, the desired thickness of the thin film, and the like.
- a carrier block layer may be provided between arbitrary layers for the purpose of controlling the rectification property of the photocurrent.
- 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 hole collection layer or the cathode. In many cases, this is not the case.
- the material forming the hole block layer include titanium oxide, zinc oxide, tin oxide, bathocuproine (BCP), 4,7-diphenyl 1,10-phenanthroline (BPhen) and the like.
- Materials for forming the electron block layer include triarylamines such as N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine ( ⁇ -NPD) and poly (triarylamine) (PTAA). Materials and the like can be mentioned.
- the carrier block layer material is a poorly soluble or poorly dispersible sublimable material
- the above-mentioned various dry processes are selected
- the carrier block layer material is a solution material or a dispersion liquid material
- the above-mentioned various dry processes are selected.
- the viscosity and surface tension of the composition, the desired thickness of the thin film, and the like the optimum one is adopted from the various wet process methods described above.
- Reverse-laminated organic thin-film solar cell A process of forming a layer of cathode material on the surface of a transparent substrate to manufacture a transparent cathode substrate.
- the cathode material is the above-mentioned forward-laminated anode material.
- FTO fluorine-doped tin oxide
- examples of the transparent substrate include those exemplified by the above-mentioned forward-laminated anode material.
- the above-mentioned dry process is selected in the case of a sparingly soluble and poorly dispersible sublimable material, and in the case of a solution material or a dispersion liquid material, the viscosity of the composition is used. Considering the surface tension, the desired thickness of the thin film, etc., the most suitable one is adopted from the various wet process methods described above. Further, in this case as well, a commercially available transparent cathode substrate can be preferably used, and from the viewpoint of improving the yield of the device, it is preferable to use a substrate that has been smoothed.
- the method for manufacturing an organic thin-film solar cell of the present invention does not include a step of forming a cathode layer.
- a transparent cathode substrate is formed by using an inorganic oxide as a cathode material, the same cleaning treatment or surface treatment as that of the forward-laminated anode material may be performed.
- Step of forming an electron collecting layer on the formed cathode For the purpose of improving the efficiency of charge transfer, if necessary, electrons are formed between the active layer and the cathode layer.
- a collection layer may be formed.
- the material for forming the electron collecting layer include zinc oxide (ZnO), titanium oxide (TIO), tin oxide (SnO), and the like, in addition to those exemplified in the above-mentioned forward laminated material.
- the above-mentioned dry process is selected in the case of a poorly soluble or poorly dispersible sublimable material, and in the case of a solution material or a dispersion liquid material, the viscosity and surface tension of the composition are desired.
- the optimum one is adopted from the various wet process methods described above. It is also possible to adopt a method in which a precursor layer of an inorganic oxide is formed on a cathode by a wet process (particularly a spin coating method or a slit coating method) and then 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. It may be a laminated thin film or a non-laminated thin film made of a mixture of these materials.
- the n-type and p-type semiconductor materials include the same as those exemplified in the above-mentioned forward-laminated semiconductor materials, but the n-type materials include PC 61 BM and PC 71 BM, and the p-type materials include PC 61 BM. , PTB7 and other polymers containing a thiophene skeleton in the main chain are preferred.
- the method for forming the active layer is also the same as the method described for the above-mentioned forward-laminated active layer.
- Step of forming a hole collecting layer on the formed layer of the active layer material According to the above method, the composition of the present invention is used on the layer of the active layer material. Form a hole collection layer.
- Step of forming an anode layer on the formed hole collecting layer Examples of the anode material include the same as the above-mentioned forward-laminated type anode material, and as a method for forming the anode layer. Is the same as that of the forward-laminated cathode layer.
- a carrier block layer may be provided between arbitrary layers for the purpose of controlling the rectification property of the photocurrent, if necessary.
- Examples of the material for forming the hole block layer and the material for forming the electron block layer include the same materials as described above, and the method for forming the carrier block layer is also the same as described above.
- the OPV produced by the method exemplified above is introduced into the glove box again in order to prevent element deterioration due to the atmosphere, and the sealing operation is performed in an atmosphere of an inert gas such as nitrogen, and the sun is sealed in a sealed state. It can function as a battery and measure the characteristics of solar cells.
- a sealing method a concave glass substrate having a UV curable resin attached to the end thereof is attached to the film formation surface side of the organic thin film solar cell element in an inert gas atmosphere, and the resin is cured by UV irradiation.
- composition for hole collecting layer [Example 1-1] 2.53 g of a polythiophene derivative (SELFTRON S, manufactured by Tosoh Corporation, 2.0% by mass aqueous solution) was diluted with 2.48 g of distilled water to prepare a dark blue solution having a solid content concentration of 1.0% by mass. The obtained dark blue solution was filtered through a syringe filter having a pore size of 0.45 ⁇ m to obtain a hole collecting layer composition B1.
- SELFTRON S manufactured by Tosoh Corporation, 2.0% by mass aqueous solution
- Example 1-2 2.53 g of a polythiophene derivative (SELFTRON S, manufactured by Toso Co., Ltd., 2.0% by mass aqueous solution) was diluted with 2.48 g of isopropanol, and a fluorine-based nonionic surfactant (FN-1287, Dai-ichi Kogyo Seiyaku Co., Ltd.) (Manufactured by) 0.5 mg was added to prepare a dark blue solution having a solid content concentration of 1.0% by mass. The obtained dark blue solution was filtered through a syringe filter having a pore size of 0.45 ⁇ m to obtain a hole collecting layer composition B2.
- SELFTRON S manufactured by Toso Co., Ltd., 2.0% by mass aqueous solution
- PEDOT / PSS (AI4083, manufactured by Heleus) was filtered through a syringe filter having a pore size of 0.45 ⁇ m to obtain a hole collecting layer composition C1.
- PEDOT / PSS (Clevios HTL Solar, manufactured by Heleus) was filtered through a syringe filter having a pore size of 0.45 ⁇ m to obtain a hole collecting layer composition C2.
- PEDOT A fluorine-based nonionic surfactant (FS-31) was added to a dark blue solution obtained by diluting 15 g of a PSS aqueous solution (Clevios P, manufactured by Heleus, 1.3 mass% aqueous dispersion) with 15 g of distilled water. (Manufactured by DuPont) was added in an amount of 0.25% by mass based on the whole dark blue solution and filtered through a syringe filter having a pore size of 0.45 ⁇ m to obtain a composition for collecting holes C3.
- FS-31 fluorine-based nonionic surfactant
- Example 2-1 Fabrication of Organic Thin-Film Solar Cell
- the composition B1 was applied by a spin coating method. This glass substrate was heated at 100 ° C. for 5 minutes using a hot plate to form a hole collecting layer.
- the film thickness of the hole collecting layer was about 30 nm.
- the solution A1 obtained in Preparation Example 1 was dropped onto the formed hole collecting layer to form a film by a spin coating method, and the active layer having a film thickness of 100 nm was formed. Formed.
- the substrate on which the organic semiconductor layer is formed and the mask for the negative electrode are installed in the vacuum vapor deposition apparatus, and the vacuum in the apparatus is exhausted until the degree of vacuum becomes 1 ⁇ 10 -3 Pa or less.
- a lithium 8-hydroxyquinolinolate layer to be a collection layer was deposited to a thickness of 1 nm.
- a forward laminated OPV having an area where the striped ITO layer and the aluminum layer intersect is 10 mm ⁇ 10 mm. Made.
- Example 2-1 A forward-stacked OPV was produced in the same manner as in Example 2-1 except that the hole-collecting layer composition C1 was used instead of the hole-collecting layer composition B1.
- Example 3-1 A 25 mm ⁇ 25 mm glass substrate in which an ITO transparent conductive layer to be a negative electrode was patterned in a stripe shape of 10 mm ⁇ 25 mm was subjected to UV / ozone treatment for 15 minutes.
- a solution of zinc oxide (manufactured by Genes' Inc.) as an electron collecting layer was dropped onto this substrate, and a film was formed by a spin coating method.
- the film thickness of the electron collecting layer was about 20 nm.
- the solution A1 obtained in Preparation Example 1 was dropped onto the formed electron collecting layer and formed into a film by a spin coating method to form an active layer.
- the hole collecting layer composition B2 prepared in Example 1-2 was applied onto this active layer by the doctor blade method, and then dried at room temperature to form a hole collecting layer.
- the film thickness of the hole collecting layer was about 300 nm.
- the laminated substrate is installed in a vacuum vapor deposition apparatus, exhausted until the degree of vacuum in the apparatus becomes 1 ⁇ 10 -3 Pa or less, and the silver layer serving as a positive electrode has a thickness of 200 nm by a resistance heating method.
- a reverse laminated OPV having an area of 3 mm ⁇ 8 mm at the intersection of the striped ITO layer and the silver layer was produced by thin-film deposition.
- Example 3-1 A reverse laminated OPV was produced by the same method as in Example 3-1 except that the hole collecting layer composition C2 was used instead of the hole collecting layer composition B2.
- PEDOT / PSS is a practical HTL by using the composition for the hole collecting layer of each example containing the polythiophene derivative containing the repeating unit represented by the formula (1). It can be seen that an OPV showing the same HTL characteristics as the above can be obtained.
- Example 4-2 After applying the hole collecting layer composition B2 by the doctor blade method, the adhesion test was carried out by the same method as in Example 4-1 except that the hole was annealed at 100 ° C. for 5 minutes using a hot plate. The laminated body of was produced.
- Example 4-1 A laminate for adhesion test was prepared by the same method as in Example 4-1 except that the hole collecting layer composition C2 was used instead of the hole collecting layer composition B2.
- Example 4-2 A laminate for adhesion test was prepared by the same method as in Example 4-2 except that the hole collecting layer composition C2 was used instead of the hole collecting layer composition B2.
- Example 4-3 A laminate for adhesion test was prepared by the same method as in Example 4-1 except that the hole collecting layer composition C3 was used instead of the hole collecting layer composition B2.
- Example 4-4 A laminate for adhesion test was prepared by the same method as in Example 4-2 except that the hole collecting layer composition C3 was used instead of the hole collecting layer composition B2.
- composition for the hole collecting layer of the present invention using the polymer represented by the formula (1), better film forming property could be obtained as compared with using other self-doped polymers.
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Abstract
Description
有機太陽電池は、活性層や電荷輸送性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。
しかし、この組成物では、密着性付与成分として金属酸化物ナノ粒子が必須であることから、このような密着性付与成分を含まない、あるいはその含有量が少なくても、活性層に対して良好な密着性を発揮する組成物の開発が望まれている。
この点に鑑み、本発明者らは、金属酸化物ナノ粒子等の密着性付与成分を添加しなくても活性層に対して優れた密着性を有する薄膜を与える組成物について、ポリチオフェンの構造という点から鋭意検討を重ねた結果、上記特許文献3のポリチオフェンに包含される化合物の中でも、環状エチレンジオキシ基がチオフェン環に縮環した構造を有し、さらにこの環状エチレンジオキシ基に結合する、スルホン酸またはスルホン酸塩基を含む所定の側鎖を有するポリチオフェン誘導体が、活性層に対する腐食性の低い、アルコールや水等のプロトン性極性溶媒に対して高溶解性を示して均一溶液を形成できるとともに、この溶液から作製した薄膜が、高い正孔輸送性を示すだけでなく、当該薄膜を、OPVの正孔捕集層とした場合に、その他の密着性付与成分を使用しなくとも活性層との良好な密着性を発揮し、良好なPCEを示すOPVが得られることを見出し、本発明を完成した。
1. 式(1)または式(1’)で表される繰り返し単位を含むポリチオフェン誘導体からなる電荷輸送性物質と、溶媒とを含む有機光電変換素子の正孔捕集層用組成物。
2. さらに、界面活性剤を含む1の有機光電変換素子の正孔捕集層用組成物。
3. 上記界面活性剤が、フッ素系界面活性剤である2の有機光電変換素子の正孔捕集層用組成物。
4. さらに、上記式(1)または式(1’)で表される繰り返し単位を含むポリチオフェン誘導体とは異なる電子受容性ドーパント物質を含む1~3のいずれかの有機光電変換素子の正孔捕集層用組成物。
5. 上記式(1)または式(1’)で表される繰り返し単位を含むポリチオフェン誘導体とは異なる電子受容性ドーパント物質が、アリールスルホン酸化合物である4の有機光電変換素子の正孔捕集層用組成物。
6. 1~5のいずれかの有機光電変換素子の正孔捕集層用組成物から得られる正孔捕集層。
7. 6の正孔捕集層を備える有機光電変換素子。
本発明の正孔捕集層用組成物は、式(1)または式(1’)で表される繰り返し単位を含むポリチオフェン誘導体からなる電荷輸送性物質と、溶媒とを含む。
これらの中でも、R1としては、炭素数1~3の直鎖状または分岐鎖状のアルキル基が好ましく、メチル基、エチル基がより好ましく、メチル基がより一層好ましい。
また、R2が置換基を有するアルキル基である場合の当該置換基としては、例えば、炭素数1~6のアルキル基、炭素数1~6のアルコキシ基、炭素数6~20のアリール基、ヒドロキシ基、アミノ基、カルボキシ基等が挙げられる。
上記炭素数1~6のアルキル基としては、上記R1で例示した基と同様のものが挙げられ、炭素数1~6のアルコキシ基としては、メトキシ、エトキシ、n-プロポキシ、i-プロポキシ、n-ブトキシ等が挙げられ、炭素数6~20のアリール基としては、フェニル、トリル、1-ナフチル、2-ナフチル、1-アントリル、2-アントリル、9-アントリル、1-フェナントリル、2-フェナントリル、3-フェナントリル、4-フェナントリル、9-フェナントリル基等が挙げられる。
特に、置換基としてはヒドロキシ基が好ましく、ヒドロキシ基を有するアルキル基としては、2-ヒドロキシエチル基、3-ヒドロキシプロピル基、2-ヒドロキシプロピル基、2,3-ジヒドロキシプロピル基等が挙げられる。
これらの中でも、R2としては、水素原子、炭素数1~3の直鎖状または分岐鎖状のアルキル基が好ましく、水素原子、メチル基がより好ましい。
公知の方法としては、例えば、特開2014-65898号公報等に記載された方法が挙げられ、下記に示されるようなチオフェンモノマーを原料とし、水またはアルコール溶媒中、酸化剤の存在下に重合させて製造することができる。
一方、市販品としては、例えば、SELFTRON(登録商標)シリーズのSELFTRON S、SELFTRON H(いずれも東ソー(株)製)等が挙げられる。
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正孔捕集層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。
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;DIC(株)製メガファックF-444、F-477、F-559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、メガファックF-559が好適である。
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。
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。
ナノ粒子とは、一次粒子についての平均粒子径がナノメートルのオーダー(典型的には500nm以下)である微粒子を意味する。金属酸化物ナノ粒子とは、ナノ粒子に成形された金属酸化物を意味する。
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W(タングステン)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、分散媒がアルコール溶媒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チオフェン誘導体に対し、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。
上記マトリックス高分子の具体例としては、下記式(I)で表される繰り返し単位および下記式(II)で表される繰り返し単位を含むマトリックス高分子を挙げることができる。
市販品としては、例えば、デュポン製のナフィオン(NAFION,登録商標)、Solvay Specialty Polymers製のアクイヴィオン(AQUIVION,登録商標)、および旭硝子(株)製のフレミオン(FLEMION,登録商標)等が挙げられる。
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0.1~50mPa・s程度である。
なお、マトリックス高分子、アルコキシシラン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。更に、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、これらはハロゲン原子、ニトロ基、シアノ基、スルホン酸基、炭素数1~20のアルコキシ基、炭素数1~20のチオアルコキシ基、炭素数1~20のアルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数1~20のハロアルキル基、炭素数6~20のアリール基、炭素数7~20のアラルキル基、または炭素数1~20のアシル基で置換されていてもよい。
炭素数1~20のチオアルコキシ(アルキルチオ)基としては、メチルチオ、エチルチオ、n-プロピルチオ、イソプロピルチオ、n-ブチルチオ、イソブチルチオ、s-ブチルチオ、t-ブチルチオ、n-ペンチルチオ、n-ヘキシルチオ、n-ヘプチルチオ、n-オクチルチオ、n-ノニルチオ、n-デシルチオ、n-ウンデシルチオ、n-ドデシルチオ、n-トリデシルチオ、n-テトラデシルチオ、n-ペンタデシルチオ、n-ヘキサデシルチオ、n-ヘプタデシルチオ、n-オクタデシルチ基、n-ノナデシルチオ、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、ジフルオロメチル、トリフルオロメチル、ペンタフルオロエチル、2,2,2-トリフルオロエチル、ヘプタフルオロプロピル、2,2,3,3,3-ペンタフルオロプロピル、2,2,3,3-テトラフルオロプロピル、2,2,2-トリフルオロ-1-(トリフルオロメチル)エチル、ノナフルオロブチル、4,4,4-トリフルオロブチル、ウンデカフルオロペンチル、2,2,3,3,4,4,5,5,5-ノナフルオロペンチル、2,2,3,3,4,4,5,5-オクタフルオロペンチル、トリデカフルオロヘキシル、2,2,3,3,4,4,5,5,6,6,6-ウンデカフルオロヘキシル、2,2,3,3,4,4,5,5,6,6-デカフルオロヘキシル、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。
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
(6)剥離試験装置:協和界面(株)製、VERSATILE PEEL ANALYZER VPA-3
[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]
ポリチオフェン誘導体(SELFTRON S、東ソー(株)製、2.0質量%水溶液)2.53gを蒸留水2.48gで希釈し、固形分濃度1.0質量%の濃青色溶液を調製した。得られた濃青色溶液を、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。
ポリチオフェン誘導体(SELFTRON S、東ソー(株)製、2.0質量%水溶液)2.53gをイソプロパノール2.48gで希釈し、フッ素系ノニオン性界面活性剤(FN-1287、第一工業製薬(株)製)0.5mgを加えて、固形分濃度1.0質量%の濃青色溶液を調製した。得られた濃青色溶液を、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。
PEDOT/PSS(AI4083、へレウス社製)を、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。
PEDOT/PSS(Clevios HTL Solar、へレウス社製)を、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C2を得た。
PEDOT:PSS水溶液(Clevios P、へレウス社製、1.3質量%水分散液)15gを蒸留水15gで希釈して得られた濃青色溶液に、フッ素系ノニオン性界面活性剤(FS-31、デュポン社製)を、濃青色溶液全体に対して0.25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C3を得た。
[実施例2-1]
正極となるITO透明導電層を10mm×25mmのストライプ状にパターニングした25mm×25mmのガラス基板を15分間UV/オゾン処理した後に、基板上に実施例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。このガラス基板を、ホットプレートを用いて、100℃5分間加熱して正孔捕集層を形成した。正孔捕集層の膜厚は約30nm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、形成した正孔捕集層上に調製例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、膜厚100nmの活性層を形成した。
次に、有機半導体層が形成された基板と負極用マスク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、電子捕集層となるリチウム8-ヒドロキシキノリノラート層を1nmの厚さに蒸着した。
最後に、抵抗加熱法によって、負極となるアルミニウム層を80nmの厚さに蒸着することで、ストライプ状のITO層とアルミニウム層とが交差する部分の面積が10mm×10mmである順積層型OPV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、順積層型OPVを作製した。
負極となるITO透明導電層を10mm×25mmのストライプ状にパターニングした25mm×25mm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社製)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1-2で調製した正孔捕集層用組成物B2をドクターブレード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300nm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、正極となる銀層を200nm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3mm×8mmである逆積層型OPVを作製した。
正孔捕集層用組成物B2の代わりに、正孔捕集層用組成物C2を用いた以外は、実施例3-1と同様の方法で、逆積層型OPVを作製した。
上記実施例2-1、3-1および比較例2-1、3-1で作製した各OPV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
[実施例4-1]
25mm×25mm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30nm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1-2で調製した正孔捕集層用組成物B2をドクターブレード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300~400nmであった。
正孔捕集層用組成物B2をドクターブレード法により塗布した後、ホットプレートを用いて100℃5分のアニール処理をした以外は、実施例4-1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B2の代わりに正孔捕集層用組成物C2を用いた以外は、実施例4-1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B2の代わりに正孔捕集層用組成物C2を用いた以外は、実施例4-2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B2の代わりに正孔捕集層用組成物C3を用いた以外は、実施例4-1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B2の代わりに正孔捕集層用組成物C3を用いた以外は、実施例4-2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4-1~4-2および比較例4-1~4-4で作製した積層体について、下記手法により、剥離試験を行った。
評価する膜に、18mm幅、付着強さ4N/cmのセロハンテープを膜面側の基板全面に対して貼り付け、約90°の方向に引張速度2mm/minで剥離を行い、密着力の評価を行った。結果を表2に示す。なお、密着力は測定範囲における最大値を示す。
Claims (7)
- さらに、界面活性剤を含む請求項1記載の有機光電変換素子の正孔捕集層用組成物。
- 上記界面活性剤が、フッ素系界面活性剤である請求項2記載の有機光電変換素子の正孔捕集層用組成物。
- さらに、上記式(1)または式(1’)で表される繰り返し単位を含むポリチオフェ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1~3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。
- 上記式(1)または式(1’)で表される繰り返し単位を含むポリチオフェン誘導体とは異なる電子受容性ドーパント物質が、アリールスルホン酸化合物である請求項4記載の有機光電変換素子の正孔捕集層用組成物。
- 請求項1~5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から得られる正孔捕集層。
- 請求項6記載の正孔捕集層を備える有機光電変換素子。
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