WO2015087797A1 - 有機薄膜太陽電池の陽極バッファ層用組成物及び有機薄膜太陽電池 - Google Patents
有機薄膜太陽電池の陽極バッファ層用組成物及び有機薄膜太陽電池 Download PDFInfo
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- WO2015087797A1 WO2015087797A1 PCT/JP2014/082228 JP2014082228W WO2015087797A1 WO 2015087797 A1 WO2015087797 A1 WO 2015087797A1 JP 2014082228 W JP2014082228 W JP 2014082228W WO 2015087797 A1 WO2015087797 A1 WO 2015087797A1
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 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
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004544 sputter deposition 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
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 125000001424 substituent group 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- MLXDKRSDUJLNAB-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MLXDKRSDUJLNAB-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- FCIABWJRBPKYJO-UHFFFAOYSA-N triethoxy(furan-3-yl)silane Chemical compound CCO[Si](OCC)(OCC)C=1C=COC=1 FCIABWJRBPKYJO-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical compound CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-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
- ZRQAIBMAFLMIND-UHFFFAOYSA-N triethoxy(thiophen-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CS1 ZRQAIBMAFLMIND-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PBTDWUVVCOLMFE-UHFFFAOYSA-N triethoxy-[4-(trifluoromethyl)phenyl]silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C(F)(F)F)C=C1 PBTDWUVVCOLMFE-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
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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
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- 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 an anode buffer layer of an organic thin film solar cell and an organic thin film solar cell.
- An organic solar cell is a solar cell element using an organic substance as an active layer or a charge transporting material.
- Organic thin-film solar cells developed by Tan are well known (Non-Patent Documents 1 and 2). All are lightweight, thin film, flexible, roll-to-roll, and other features that are different from the current mainstream inorganic solar cells. Formation is expected.
- organic thin-film solar cells hereinafter abbreviated as OPV
- OPV organic thin-film solar cells
- PCE photoelectric conversion efficiency
- Non-Patent Document 3 In recent years, the use of renewable energy has been proposed and its development is being accelerated. In OPV, studies have been made in order to quickly put it into practical use as a device such as energy harvesting. After that, it is expected to spread to a wider range of applications.
- PEDOT / PSS which is often used as an anode buffer layer in OPV, is prepared as an aqueous dispersion, and it is very difficult to completely remove moisture and suppress re-absorption. There is a problem that it is easy.
- the PEDOT / PSS aqueous dispersion tends to agglomerate solids, there are problems such as coating film defects, clogging and corrosion of the coating apparatus, and problems remain in the mass production process. It had been.
- This invention is made
- the inventors of the present invention have a composition containing an aryldiamine derivative and an electron-accepting dopant substance that is completely dissolved in an organic solvent to form a uniform solution,
- the present inventors have found that an organic thin film solar cell having excellent photoelectric conversion characteristics can be obtained by using a thin film obtained from this uniform solution as an anode buffer layer of an organic thin film solar cell, thereby completing the present invention.
- a composition for an anode buffer layer of an organic thin film solar cell comprising a charge transporting material comprising an aryldiamine derivative represented by formula (1), an electron-accepting dopant material, and an organic solvent; ⁇ Wherein R 1 to R 4 each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, or a carbon number of 1 to 20 An alkoxy group, a thioalkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a bicycloalkyl group having 6 to 20 carbon atoms.
- An alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms; 5 to R 8 are each independently a hydrogen atom, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, furanyl group, pyrrolyl group, pyrazolyl group, imidazolyl.
- thienyl group (these groups are halogen atom, nitro group, cyano group, hydroxyl group, thiol group, phosphoric acid group, sulfonic acid group, carboxyl group, alkoxy group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, A thioalkoxy group, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a bicycloalkyl group having 6 to 20 carbon atoms, and an alkenyl group having 2 to 20 carbon atoms May be substituted with an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms or an acyl group having 1 to 20 carbon atoms), or a formula (2 (Wherein at least one of R 5 to flu
- An alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms; 13 and R 14 are each independently phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, a pyrazolyl group, Imi Zolyl group, thienyl group (these groups may be bonded to each other to form a ring, and also a halogen atom, nitro group, cyano group, hydroxyl group, thiol group, phosphoric acid group, sulfonic acid group, carboxyl group, An alk
- organic thin-film solar cells in which the active layer contains a polymer containing a thiophene skeleton in the main chain; 11.
- composition of the present invention can be produced not only by using a commercially available compound in the market, but also by using an organic thin film solar cell excellent in photoelectric conversion efficiency when a thin film obtained therefrom is used as an anode buffer layer. Obtainable.
- composition for an anode buffer layer of the organic thin film solar cell of the present invention comprises an aryldiamine derivative represented by the above formula (1), an electron-accepting dopant substance, and an organic solvent.
- R 1 to R 4 each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, an alkoxy group having 1 to 20 carbon atoms, carbon A thioalkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a bicycloalkyl group having 6 to 20 carbon atoms, and 2 carbon atoms Represents an alkenyl group having -20 carbon atoms, an alkynyl group having 2-20 carbon atoms, an aryl group having 6-20 carbon atoms, an aralkyl group having 7-20 carbon atoms, or an acyl group having 1-20 carbon atoms
- examples of the halogen atom include fluorine, chlorine, bromine and iodine atoms.
- Specific examples of the alkoxy group having 1 to 20 carbon atoms include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, c-propoxy group, n-butoxy group, i-butoxy group, 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-oct
- thioalkoxy (alkylthio) group having 1 to 20 carbon atoms include methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, s-butylthio group, 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-tetra
- alkyl group having 1 to 20 carbon atoms examples 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.
- haloalkyl group having 1 to 20 carbon atoms examples include those obtained by substituting at least one hydrogen atom of the alkyl group having 1 to 20 carbon atoms with a halogen atom. Among them, a fluoroalkyl group is preferable, and perfluoro An alkyl group is more preferred.
- 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 Pentyl group, tridecafluorohexyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, 2,2,3,3,4,4,4 5,5,6,6-Decafluo Hexyl group
- cycloalkyl group having 3 to 20 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a cyclononyl group.
- the bicycloalkyl group having 6 to 20 carbon atoms include a bicyclopropyl group, a bicyclobutyl group, a bicyclopentyl group, a bicyclohexyl group, a bicycloheptyl group, a bicyclooctyl group, and a bicyclononyl group.
- alkenyl group having 2 to 20 carbon atoms include vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-2-propenyl group, 2-butenyl group, 3-butenyl group, and 2-pentenyl group.
- 3-pentenyl group 4-pentenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 3,7-dimethyl-6-octenyl Group, 8-nonenyl group, 9-decenyl group, 10-undecenyl group, 11-dodecenyl group, 12-tridecenyl group, 13-tetradecenyl group, 14-pentadecenyl group, 15-hexadecenyl group, 16-heptadecenyl group, 17-octadecenyl group Group, 18-nonadecenyl group, 19-eicocenyl group and the like.
- alkynyl group having 2 to 20 carbon atoms include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 2-butynyl group, 3-butynyl group and 2-pentynyl group.
- 3-pentynyl group 4-pentynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 6-heptynyl group, 7-octynyl group, 3,7-dimethyl-6-octynyl Group, 8-nonynyl group, 9-decynyl group, 10-undecynyl group, 11-dodecynyl group, 12-tridecynyl group, 13-tetradecynyl group, 14-pentadecynyl group, 15-hexadecynyl group, 16-heptadecynyl group, 17-octadecynyl group Group, 18-nonadecynyl group, 19-eicosinyl group and the like.
- aryl group having 6 to 20 carbon atoms include phenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, anthryl group, phenanthrenyl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group and the like. It is done.
- aralkyl group having 7 to 20 carbon atoms include benzyl group, phenylethyl group, phenylpropyl group, naphthylmethyl group, naphthylethyl group, naphthylpropyl group and the like.
- acyl group having 1 to 20 carbon atoms include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, benzoyl group and the like.
- R 1 to R 4 are each a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms.
- a perfluoroalkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms are preferable, and all hydrogen atoms are optimal.
- R 5 to R 8 are each independently a hydrogen atom, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, furanyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thienyl group (these The group includes a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, and 1 carbon atom.
- Others represents a group represented by the above formula (2), at least one of R 5 ⁇ R 8 is a hydrogen atom.
- R 9 to R 12 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, a carboxyl group, or a carbon number of 1 -20 alkoxy group, thioalkoxy group having 1-20 carbon atoms, alkyl group having 1-20 carbon atoms, haloalkyl group having 1-20 carbon atoms, cycloalkyl group having 3-20 carbon atoms, 6-20 carbon atoms A bicycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms.
- R 13 and R 14 are each independently phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a furanyl group, a pyrrolyl group, Pila A ryl group, an imidazolyl group, a thienyl group (these groups may be bonded to each other to form a ring, and a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a phosphoric acid group, a sulfonic acid group, A carboxyl 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, a haloalkyl group having 1 to 20 carbon atoms,
- a halogen atom 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, a haloalkyl group having 1 to 20 carbon atoms, carbon A cycloalkyl group having 3 to 20 carbon atoms, a bicycloalkyl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 7 carbon atoms
- Specific examples of the 20 aralkyl group and the acyl group having 1 to 20 carbon atoms are the same as described above.
- R 5 and R 7 are both hydrogen atoms
- R 6 and R 8 are both Most preferably it is a phenyl group.
- the aryldiamine derivative represented by the formula (1) may be a commercially available product or a benzidine or diaminoterphenyl as a starting material and may be prepared by a known method. Before preparing the buffer layer composition, it is preferable to use one purified by recrystallization or vapor deposition. By using the purified one, the characteristics of the OPV element including the thin film obtained from the composition can be further improved. In the case of purification by recrystallization, for example, 1,4-dioxane, tetrahydrofuran or the like can be used as the solvent.
- the molecular weight of the aryldiamine derivative represented by the formula (1) is not particularly limited, but considering the conductivity, the lower limit is usually 200 or more, preferably 300 or more, and the solubility in a solvent is improved. In view of the above, the upper limit is usually 5000 or less, preferably 2000 or less.
- the aryldiamine derivative represented by the formula (1) is one compound selected from the aryldiamine derivatives represented by the formula (1) (that is, dispersion of molecular weight distribution).
- the degree 1) may be used alone, or two or more compounds may be used in combination.
- the electron-accepting dopant substance that is the other component contained in the anode buffer layer composition of the present invention is not particularly limited as long as it is soluble in at least one solvent used in the anode buffer layer composition.
- the electron-accepting dopant material 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 ), boron tribromide (BBr 3 ), boron trifluoride ether complex (BF 3 ⁇ OEt 2 ), iron chloride (III) (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, tosylic acid, camphorsulfonic acid Hydroxybenzenesulfonic acid, 5-sulfo
- inorganic oxidizing agents such as phosphomolybdic acid, phosphotungstic acid, and phosphotungstomolybdic acid such as phosphotungstomolybdic acid described in International Publication No. 2010/058777. These may be used in combination.
- arylsulfonic acid compounds are preferable, and arylsulfonic acid compounds represented by the formula (3) are particularly preferable.
- X represents O
- A represents a naphthalene ring or an anthracene ring
- B represents a divalent to tetravalent perfluorobiphenyl group
- l represents the number of sulfonic acid groups bonded to A.
- organic solvent used for the preparation of the anode buffer layer composition a highly soluble solvent that can dissolve the aryldiamine derivative and the electron-accepting dopant substance satisfactorily can be used.
- Highly soluble solvents can be used singly or in combination of two or more, and the amount used can be 5 to 100% by mass with respect to the total solvent used in the composition.
- Examples of such highly soluble solvents include N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, N-methylacetamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1, Examples include 3-dimethyl-2-imidazolidinone.
- N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, N-methylacetamide, and N, N-dimethylacetamide are preferred, and N, N-dimethylacetamide is more preferred. preferable.
- both the charge transporting substance and the electron-accepting dopant substance are completely dissolved or uniformly dispersed in the organic solvent to give an organic thin film solar cell with high conversion efficiency.
- these substances are completely dissolved in the organic solvent.
- the composition for the anode buffer layer of the present invention has a viscosity of 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., and a high viscosity organic material having a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure. It is preferable to contain at least one solvent.
- the high-viscosity organic solvent is not particularly limited.
- cyclohexanol ethylene glycol, 1,3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, 1,3-butanediol 2,3-butanediol, 1,4-butanediol, propylene glycol, hexylene glycol and the like.
- the addition ratio of the high-viscosity organic solvent with respect to the total solvent used in the composition of the present invention is preferably within a range in which no solid precipitates.
- the addition ratio is 5 to 80% by mass as long as no solid precipitates. Preferably there is.
- solvents that can provide film flatness during heat treatment for the purpose of improving the wettability to the coated surface, adjusting the surface tension of the solvent, adjusting the polarity, adjusting the boiling point, etc., are used in the composition. It is also possible to mix at 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, ethyl carbitol, Examples include, but are not limited to, diacetone alcohol, ⁇ -butyrolactone, ethyl lactate, and n-hexyl acetate.
- the composition for the anode buffer layer of the present invention desirably contains an organosilane compound from the viewpoint of improving the conversion efficiency of the obtained solar cell.
- organosilane compound include trialkoxysilane, dialkoxysilane, and the like.
- aryltrialkoxysilane, aryldialkoxysilane, fluorine atom-containing trialkoxysilane, and fluorine atom-containing dialkoxysilane compound are preferable.
- the silane compound represented by S1) or (S2) is more preferable.
- R represents a fluoroalkyl group having 1 to 6 carbon atoms.
- fluoroalkyl group having 1 to 6 carbon atoms include trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 3,3, 3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 4,4,4-trifluorobutyl Group, 3,3,4,4,4-pentafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,1,2,2,3,3,4, Examples include 4,4-nonafluorobutyl group.
- dialkoxysilane compounds include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, methylpropyldimethoxysilane, methylpropyldiethoxysilane, diisopropyldimethoxysilane, and phenylmethyl.
- Dimethoxysilane vinylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- (3,4-epoxycyclohexyl) ethylmethyldimethoxysilane, 3-methacryloxy Propylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-mercaptopropylmethyldimethoxysilane, ⁇ -aminopropi Methyl diethoxy silane, N- (2- aminoethyl) aminopropyl methyl dimethoxy silane, such as 3,3,3-trifluoropropyl methyl dimethoxy silane.
- trialkoxysilane compounds include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, Pentyltrimethoxysilane, pentyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxy Silane, octadecyltrimethoxysilane, o
- the content of the organosilane compound is usually about 0.1% by mass to 200% by mass with respect to the charge transporting material and the electron accepting dopant material of the composition of the present invention, preferably, It is 1% by mass to 50% by mass, more preferably 5% by mass to 20% by mass.
- 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 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.
- solid content means components other than the organic solvent which comprise the composition for anode buffer layers.
- the substance amount (mol) ratio between the charge transporting substance and the electron-accepting dopant substance is also appropriately set in consideration of the type of charge transporting property, charge transporting substance, etc. that are expressed. With respect to the transporting substance 1, the electron-accepting dopant substance is 0.1 to 10, preferably 0.5 to 5.0, and more preferably 0.5 to 3.0.
- the viscosity of the composition for the anode buffer 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. It is about 1 mPa ⁇ s to 50 mPa ⁇ s.
- the charge transporting substance, the electron accepting dopant substance, and the organic solvent can be mixed in any order as long as the solid content is uniformly dissolved or dispersed in the solvent. That is, for example, after dissolving an aryldiamine derivative in an organic solvent, a method of dissolving the electron-accepting dopant substance in the solution, and after dissolving the electron-accepting dopant substance in the organic solvent, the aryldiamine derivative is added to the solution. Any of the methods of dissolving, mixing the aryldiamine derivative and the electron-accepting dopant substance, and then adding the mixture to the organic solvent to dissolve will be adopted as long as the solid content is uniformly dissolved or dispersed in the organic solvent. can do.
- the composition is usually prepared 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 changes greatly. ) Or may be performed while heating.
- the anode buffer layer of the present invention can be formed by applying the composition for an anode buffer layer described above to the anode of an organic thin film solar cell and baking it.
- drop casting method, spin coating method, blade coating method, dip coating method, roll coating method, bar coating method, die coating method What is necessary is just to employ
- the coating is performed in an inert gas atmosphere at normal temperature and pressure, but it is performed in an air atmosphere (in the presence of oxygen) unless the compound in the composition is decomposed or the composition is largely changed. It may be performed while heating.
- the film thickness is usually preferably about 5 to 200 nm, and methods for changing the film thickness include methods such as changing the solid content concentration in the composition or changing the amount of solution during coating.
- anode layer A step of forming a layer of anode material on the surface of the transparent substrate to produce a transparent electrode.
- anode material metal oxide such as indium tin oxide (ITO) and indium zinc oxide (IZO) is used.
- high charge transporting organic compounds such as polythiophene derivatives and polyaniline derivatives can be used.
- transparent substrate a substrate made of glass or transparent resin can be used.
- the method for forming the anode material layer is appropriately selected according to the properties of the anode material, and is usually a dry process using a sublimation compound (evaporation method) or a wet process using a varnish containing a charge transporting compound. Either process (especially spin coating or slit coating) is employed.
- a commercial item can also be used suitably as a transparent electrode, and it is preferable to use the base
- the manufacturing method of the organic thin-film solar cell of this invention does not include the process of forming an anode layer.
- the transparent electrode to be used is preferably used after being washed with a detergent, alcohol, pure water or the like.
- the anode substrate is preferably subjected to a surface treatment such as UV ozone treatment or oxygen-plasma treatment immediately before use (when the anode material is mainly composed of an organic substance, the surface treatment may not be performed).
- Step of forming an anode buffer layer on the formed anode material layer Step of forming an anode buffer layer on the formed anode material layer According to the above method, a buffer layer is formed on the anode material layer using the composition of the present invention.
- the active layer includes 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. Or a non-laminated thin film made 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), and the like. Can be mentioned.
- regioregular poly (3-hexylthiophene) P3HT
- PTB7 formula (4)
- PDTP-DFBT formula (5)
- JP 2009-158921 A JP 2009-158921 A
- international publication Examples include polymers containing a thiophene skeleton in the main chain such as thienothiophene unit-containing polymers as described in No. 2010/008672, phthalocyanines such as CuPC and ZnPC, and porphyrins such as tetrabenzoporphyrin. .
- n-type material PC 61 BM and PC 71 BM are preferable
- p-type material polymers including a thiophene skeleton in the main chain such as PTB7 are preferable.
- thiophene skeleton in the main chain refers to a divalent aromatic ring composed solely of thiophene, or thienothiophene, benzothiophene, dibenzothiophene, benzodithiophene, naphthothiophene, naphthodithiophene, anthrathiophene, anthracodi.
- the formation method of the active layer is appropriately selected according to the properties of the n-type semiconductor or the p-type semiconductor material, and is usually a dry process using a sublimation compound (particularly vapor deposition method) or a wet process using a varnish containing a material ( In particular, either a spin coat method or a slit coat method is employed.
- Step of forming a cathode buffer layer on the formed active layer A cathode buffer between the active layer and the cathode layer for the purpose of improving the efficiency of charge transfer, if necessary.
- a layer may be formed.
- Materials for forming the cathode buffer layer include lithium oxide (Li 2 O), magnesium oxide (MgO), alumina (Al 2 O 3 ), lithium fluoride (LiF), magnesium fluoride (MgF 2 ), and strontium fluoride. (SrF 2 ) and the like.
- the method for forming the cathode buffer layer is appropriately selected according to the properties of the material, and is usually a dry process using a sublimation compound (especially vapor deposition) or a wet process using a varnish containing a material (especially spin coating).
- a dry process using a sublimation compound especially vapor deposition
- a wet process using a varnish containing a material especially spin coating.
- One of the slit coating methods is employed.
- Step of forming a cathode layer on the formed cathode buffer layer As cathode materials, aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium, calcium, barium Silver, gold, and the like, and a plurality of cathode materials can be laminated or mixed for use.
- the method for forming the cathode buffer layer is appropriately selected according to the properties of the material, but usually a dry process (especially vapor deposition) is employed.
- a carrier block layer may be provided between arbitrary layers for the purpose of controlling photocurrent rectification.
- the material for forming the carrier block layer include titanium oxide and zinc oxide.
- the method for forming the carrier block layer is appropriately selected according to the properties of the material. Usually, the vapor deposition method is used when a sublimation compound is used, and the spin coating method or the slit coating method is used when a varnish in which the material is dissolved is used. Either one is adopted.
- the OPV device manufactured by the method exemplified above is again introduced into the glove box and sealed in an inert gas atmosphere such as nitrogen in order to prevent device deterioration due to the atmosphere.
- the function as a solar cell can be exhibited, or the solar cell characteristics can be measured.
- a sealing method a concave glass substrate with a UV curable resin attached to the end is attached to the film forming surface side of the organic thin film solar cell element in an inert gas atmosphere, and the resin is cured by UV irradiation. Examples of the method include performing a film sealing type sealing by a technique such as sputtering under vacuum.
- composition for active layer [Preparation Example 1] Sample bottle containing 40 mg of regioregular poly (3-hexylthiophene) (Merck, product name: lisicon (registered trademark) SP-001) and 32 mg of PC 61 BM (manufactured by Frontier Carbon, product name: nanom spectra E100) Then, 2.0 mL of chlorobenzene was added and stirred on a hot plate at 80 ° C. for 15 hours to obtain a solution A1 (composition for active layer).
- regioregular poly (3-hexylthiophene) Merck, product name: lisicon (registered trademark) SP-001
- PC 61 BM manufactured by Frontier Carbon, product name: nanom spectra E100
- anode buffer layer composition B1 5.0 g of cyclohexanol was added thereto and stirred to obtain a pale yellow solution.
- the obtained pale yellow solution was filtered with a syringe filter having a pore size of 0.2 ⁇ m to obtain an anode buffer layer composition B1.
- PEDOT / PSS (Clevios P VP CH8000 manufactured by Heraeus) was filtered through a syringe filter having a pore diameter of 0.45 ⁇ m to obtain an anode buffer layer composition C1.
- the substrate on which the organic semiconductor layer is formed and the negative electrode mask are placed in a vacuum deposition apparatus, and the vacuum in the apparatus is exhausted to 1 ⁇ 10 ⁇ 3 Pa or less, and the negative electrode is formed by resistance heating.
- An aluminum layer was deposited to a thickness of 80 nm.
- an OPV element having an area where the stripe-shaped ITO layer intersects with the aluminum layer was 2 mm ⁇ 2 mm was produced.
- Example 2 An OPV element was produced in the same manner as in Example 1 except that the anode buffer layer composition B2 was used instead of the anode buffer layer composition B1.
- Example 3 After a 20 mm ⁇ 20 mm glass substrate obtained by patterning an ITO transparent conductive layer serving as a positive electrode in a 2 mm ⁇ 20 mm stripe pattern for 15 minutes by UV / ozone treatment, the anode buffer layer composition B1 prepared on the substrate was spin-coated. Applied. This glass substrate was heated at 50 ° C. for 5 minutes and further at 230 ° C. for 20 minutes using a hot plate to form a buffer layer having a thickness of 30 nm. Thereafter, in a glove box substituted with an inert gas, the solution A2 was dropped on the formed buffer layer, and a film was formed by spin coating.
- the substrate on which the organic semiconductor layer is formed and the negative electrode mask are placed in a vacuum deposition apparatus, and the vacuum in the apparatus is exhausted to 1 ⁇ 10 ⁇ 3 Pa or less, and the negative electrode is formed by resistance heating.
- An aluminum layer was deposited to a thickness of 80 nm.
- an OPV element having an area of 2 mm ⁇ 2 mm where the stripe-like ITO layer intersects with the aluminum layer was produced by heating at 90 ° C. for 10 minutes with a hot plate.
- Example 4 An OPV element was produced in the same manner as in Example 3 except that the anode buffer layer composition B2 was used instead of the anode buffer layer composition B1.
- Example 5 An OPV device was produced in the same manner as in Example 3 except that the active layer composition A3 was used instead of the active layer composition A2.
- Example 6 The same method as in Example 3 except that the active layer composition A3 was used instead of the active layer composition A2, and the anode buffer layer composition B3 was used instead of the anode buffer layer composition B1.
- An OPV device was manufactured.
- Example 7 An OPV element was produced in the same manner as in Example 3 except that the anode buffer layer composition B3 was used instead of the anode buffer layer composition B1.
- Example 8 An OPV element was produced in the same manner as in Example 3 except that the anode buffer layer composition B4 was used instead of the anode buffer layer composition B1.
- Example 9 An OPV element was produced in the same manner as in Example 3 except that the anode buffer layer composition B5 was used instead of the anode buffer layer composition B1.
- Example 1 instead of the anode buffer layer composition B1, the anode buffer layer composition C1 was used in the same manner as in Example 1 except that the anode buffer layer composition C1 was heated at 150 ° C. for 20 minutes instead of being heated at 230 ° C. for 20 minutes. An OPV element was produced.
- Example 2 instead of the anode buffer layer composition B1, the anode buffer layer composition C1 was used in the same manner as in Example 3 except that the anode buffer layer composition C1 was heated at 150 ° C. for 20 minutes instead of being heated at 230 ° C. for 20 minutes. An OPV element was produced.
- composition A3 for active layer instead of composition A2 for active layer, using composition C1 for anode buffer layer instead of composition B1 for anode buffer layer, and heating at 230 ° C. for 20 minutes, An OPV element was fabricated in the same manner as in Example 3 except that heating was performed at 150 ° C. for 20 minutes.
- Table 4 shows the evaluation results when the composition of the anode buffer layer composition was changed (Examples 4, 7, 8, and 9).
- an OPV device including a thin film obtained from the composition for an anode buffer layer of the present invention as an anode buffer layer is generally used for PEDOT.
- an OPV device provided with a thin film obtained from / PSS as an anode buffer layer high photoelectric conversion efficiency (PCE) was exhibited.
- PCE photoelectric conversion efficiency
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Abstract
Description
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。
なかでも、有機薄膜太陽電池(以下OPVと略す)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)。
近年、再生可能エネルギーの利用が提唱され、その開発が加速されつつある。OPVにおいてはエネルギーハーベスティング等のデバイスとして早期に実用化するために検討がなされている。そして、その後さらに広範囲の用途に普及することが見込まれている。
しかし、OPVにおいて陽極バッファ層としてよく用いられているPEDOT/PSSは水分散液として調製されており、水分の完全な除去や再吸収の抑制が非常に難しいために、OPV素子の劣化を加速させやすいという問題がある。また、PEDOT/PSS水分散液は固形分が凝集しやすいために、塗布膜の欠陥が生じやすい、塗布装置の目詰まりや腐食を発生させやすい等の問題があり、量産工程においても課題が残されていた。
1. 式(1)で表されるアリールジアミン誘導体からなる電荷輸送性物質と、電子受容性ドーパント物質と、有機溶媒とを含むことを特徴とする有機薄膜太陽電池の陽極バッファ層用組成物、
2. 前記R5及びR7が、水素原子であり、前記R6及びR8が、フェニル基である1の有機薄膜太陽電池の陽極バッファ層用組成物、
3. 前記nが、2または3である1または2の有機薄膜太陽電池の陽極バッファ層用組成物
4. 前記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を含む1~3のいずれかの有機薄膜太陽電池の陽極バッファ層用組成物、
5. 前記アリールスルホン酸化合物が、式(3)で表される4の有機薄膜太陽電池の陽極バッファ層用組成物、
6. 前記Xが、Oを表し、前記Aが、ナフタレン環またはアントラセン環を表す5の有機薄膜太陽電池の陽極バッファ層用組成物、
7. 有機シラン化合物を含む1~6のいずれかの有機薄膜太陽電池の陽極バッファ層用組成物、
8. 1~7のいずれかの有機薄膜太陽電池の陽極バッファ層用組成物から作製された陽極バッファ層と、それに接するように設けられた活性層とを有する有機薄膜太陽電池、
9. 前記活性層が、フラーレン誘導体を含む8の有機薄膜太陽電池、
10. 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8の有機薄膜太陽電池、
11. 前記活性層が、フラーレン誘導体及び主鎖にチオフェン骨格を含むポリマーを含む8の有機薄膜太陽電池
を提供する。
本発明の有機薄膜太陽電池の陽極バッファ層用組成物は、上記式(1)で表されるアリールジアミン誘導体と、電子受容性ドーパント物質と、有機溶媒とを含むものである。
炭素数1~20のアルコキシ基の具体例としては、メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、c-プロポキシ基、n-ブトキシ基、i-ブトキシ基、s-ブトキシ基、t-ブトキシ基、n-ペントキシ基、n-ヘキソキシ基、n-ヘプチルオキシ基、n-オクチルオキシ基、n-ノニルオキシ基、n-デシルオキシ基、n-ウンデシルオキシ基、n-ドデシルオキシ基、n-トリデシルオキシ基、n-テトラデシルオキシ基、n-ペンタデシルオキシ基、n-ヘキサデシルオキシ基、n-ヘプタデシルオキシ基、n-オクタデシルオキシ基、n-ノナデシルオキシ基、n-エイコサニルオキシ基などが挙げられる。
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-ウンデカフロオロヘキシル基、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などが挙げられる。
炭素数6~20のビシクロアルキル基の具体例としては、ビシクロプロピル基、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、ビシクロノニル基などが挙げられる。
炭素数7~20のアラルキル基の具体例としては、ベンジル基、フェニルエチル基、フェニルプロピル基、ナフチルメチル基、ナフチルエチル基、ナフチルプロピル基などが挙げられる。
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、ベンゾイル基などが挙げられる。
本発明の陽極バッファ層用組成物において、式(1)で表されるアリールジアミン誘導体としては、式(1)で表されるアリールジアミン誘導体から選ばれる1種の化合物(すなわち、分子量分布の分散度が1)を単独で用いてもよく、2以上の化合物を組み合わせて用いてもよい。
有機シラン化合物としては、トリアルコキシシラン、ジアルコキシシランなどが挙げられるが、とりわけ、アリールトリアルコキシシラン、アリールジアルコキシシラン、フッ素原子含有トリアルコキシシラン、フッ素原子含有ジアルコキシシラン化合物が好ましく、式(S1)または(S2)で表されるシラン化合物がより好ましい。
なお、固形分とは、陽極バッファ層用組成物を構成する、有機溶媒以外の成分を意味する。
また、電荷輸送性物質と電子受容性ドーパント物質の物質量(mol)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0.1~10、好ましくは0.5~5.0、より好ましくは0.5~3.0である。
そして、本発明において用いる陽極バッファ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。
塗布の際、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)など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。
膜厚は、通常5~200nm程度が好ましく、膜厚を変化させる方法としては、組成物中の固形分濃度を変化させたり、塗布時の溶液量を変化させたりするなどの方法がある。
[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)等の金属酸化物や、ポリチオフェン誘導体、ポリアニリン誘導体などの高電荷輸送性有機化合物を用いることができる。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、通常、昇華性化合物を用いたドライプロセス(蒸着法)か電荷輸送性化合物を含むワニスを用いたウェットプロセス(特にスピンコート法かスリットコート法)のいずれかが採用される。
また、透明電極として市販品も好適に用いることができ、この場合、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盤を用いることが好ましい。市販品を用いる場合、本発明の有機薄膜太陽電池の製造方法は、陽極層を形成する工程を含まない。
使用する透明電極は、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。例えば、陽極基板では、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バッファ層を形成する。
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。
n型半導体材料としては、フラーレン、[6,6]-フェニル-C61-酪酸メチルエステル(PC61BM)、[6,6]-フェニル-C71-酪酸メチルエステル(PC71BM)等が挙げられる。一方、p型半導体材料としては、レジオレギュラーポリ(3-ヘキシルチオフェン)(P3HT)、PTB7(式(4))、PDTP-DFBT(式(5))、特開2009-158921号公報及び国際公開第2010/008672号に記載されているようなチエノチオフェンユニット含有ポリマー類等の、主鎖にチオフェン骨格を含むポリマー、CuPC,ZnPC等のフタロシアニン類、テトラベンゾポルフィリン等のポルフィリン類、などが挙げられる。
これらの中でも、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。
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などのような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~R8で示される置換基で置換されていてもよい。
活性層の形成方法は、n型半導体あるいはp型半導体材料の性質に応じて適宜選択され、通常、昇華性化合物を用いたドライプロセス(特に蒸着法)か材料を含むワニスを用いたウェットプロセス(特にスピンコート法かスリットコート法)のいずれかが採用される。
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陰極バッファ層を形成してもよい。
陰極バッファ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)、フッ化マグネシウム(MgF2)、フッ化ストロンチウム(SrF2)などが挙げられる。
陰極バッファ層の形成方法は、その材料の性質に応じて適宜選択され、通常、昇華性化合物を用いたドライプロセス(特に蒸着法)か材料を含むワニスを用いたウェットプロセス(特にスピンコート法かスリットコート法)のいずれかが採用される。
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、金などが挙げられ、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。
陰極バッファ層の形成方法は、その材料の性質に応じて適宜選択されるが、通常、ドライプロセス(特に蒸着法)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形成する材料としては、酸化チタン、酸化亜鉛などが挙げられる。
キャリアブロック層の形成方法は、その材料の性質に応じて適宜選択され、通常、昇華性化合物を用いる場合は蒸着法が、材料が溶解したワニスを用いる場合はスピンコート法か、スリットコート法のいずれかが採用される。
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]使用した装置
(1)NMR
装置:日本電子(株)製 ECX-300
測定溶媒:純正化学(株)製 ジメチルスルホキシド-d6
(2)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
(3)蒸着装置:アオヤマエンジニアリング(株)製、真空蒸着装置
(4)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
(5)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
[調製例1]
レジオレギュラーポリ(3-ヘキシルチオフェン)(メルク社製、製品名:lisicon(登録商標)SP-001)40mg及びPC61BM(フロンティアカーボン社製、製品名:nanom spectra E100)32mg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時間撹拌して溶液A1(活性層用組成物)を得た。
PTB7(1-Material社製)20mg及び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、撹拌することによって溶液A2(活性層用組成物)を得た。
PDTP-DFBT(1-Material社製)20mg及び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、撹拌することによって溶液A3(活性層用組成物)を得た。
[調製例4]
N,N’-ジフェニルベンジジン(東京化成工業(株)製、以下同様)132.1mg(0.393mmol)と、国際公開第2006/025342号記載の方法に従って合成した上記式(3-1)式で表されるアリールスルホン酸化合物177.2mg(0.196mmol)との混合物に、N,N-ジメチルアセトアミド5.0gを加えて、室温で超音波を照射しながら撹拌して溶解させた。更にそこへ、シクロヘキサノール5.0gを加えて撹拌し、淡黄色溶液を得た。得られた淡黄色溶液を、孔径0.2μmのシリンジフィルターでろ過して、陽極バッファ層用組成物B1を得た。
N,N-ジメチルアセトアミド10.0gにフェニルトリメトキシシラン(信越化学工業(株)製)0.717mg(3.61mmol)と、3,3,3-トリフルオロプロピルトリメトキシシラン(信越化学工業(株)製)0.394mg(1.81mmol)とを加えて室温で撹拌し、シラン化合物溶液S1を得た。
1,3-ジメチル-2-イミダゾリジノン10.0gにフェニルトリメトキシシラン(信越化学工業(株)製)0.717mg(3.61mmol)と、3,3,3-トリフルオロプロピルトリメトキシシラン(信越化学工業(株)製)0.394mg(1.81mmol)とを加えて室温で撹拌し、シラン化合物溶液S2を得た。
N,N’-ジフェニルベンジジン92.5mg(0.275mmol)と、国際公開第2006/025342号記載の方法に従って合成した上記式(3-1)式で表されるアリールスルホン酸化合物186.1mg(0.206mmol)との混合物に、N,N-ジメチルアセトアミド4.72gを加え、室温で超音波を照射しながら撹拌して溶解させた。更にそこへ、シクロヘキサノール5.0gを加えて撹拌後、シラン化合物溶液S1 0.31gを加え、淡黄色溶液を得た。
得られた淡黄色溶液を、孔径0.2μmのシリンジフィルターでろ過して、陽極バッファ層用組成物B2を得た。
N,N’-ジフェニルベンジジン61.0mg(0.181mmol)と、国際公開第2006/025342号記載の方法に従って合成した上記式(3-1)式で表されるアリールスルホン酸化合物122.8mg(0.136mmol)との混合物に、N,N-ジメチルアセトアミド4.82gを加えて、室温で超音波を照射しながら撹拌して溶解させた。更にそこへ、シクロヘキサノール5.0gを加えて撹拌後、シラン化合物溶液S1 0.21gを加え、淡黄色溶液を得た。
得られた淡黄色溶液を、孔径0.2μmのシリンジフィルターでろ過して、陽極バッファ層用組成物B3を得た。
N,N’-ジフェニルベンジジン61.0mg(0.181mmol)と、国際公開第2006/025342号記載の方法に従って合成した上記式(3-1)式で表されるアリールスルホン酸化合物122.8mg(0.136mmol)との混合物に、N,N-ジメチルアセトアミド3.15gと2,3-ブタンジオール1.67gとを加えて、室温で超音波を照射しながら撹拌して溶解させた。更にそこへ、シクロヘキサノール5.0gを加えて撹拌後、シラン化合物溶液S1 0.21gを加え、淡褐色溶液を得た。
得られた淡褐色溶液を、孔径0.2μmのシリンジフィルターでろ過して、陽極バッファ層用組成物B4を得た。
N,N’-ジフェニルベンジジン61.0mg(0.181mmol)と、国際公開第2006/025342号記載の方法に従って合成した上記式(3-1)式で表されるアリールスルホン酸化合物122.8mg(0.136mmol)との混合物に、1,3-ジメチル-2-イミダゾリジノン3.15gとプロピレングリコール1.67gとを加え、室温で超音波を照射しながら撹拌して溶解させた。更にそこへ、シクロヘキサノール5.0gを加えて撹拌後、シラン化合物溶液S2 0.21gを加えて、淡褐色溶液を得た。
得られた淡褐色溶液を、孔径0.2μmのシリンジフィルターでろ過して、陽極バッファ層用組成物B5を得た。
PEDOT/PSS(Heraeus製Clevios P VP CH8000)を孔径0.45μmのシリンジフィルターでろ過して、陽極バッファ層用組成物C1を得た。
[実施例1]
正極となる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/オゾン処理した後に、陽極バッファ層用組成物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、50℃で5分間、さらに230℃で20分間加熱することで膜厚30nmのバッファ層を形成した。
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、形成したバッファ層上に溶液A1を滴下し、スピンコート法により成膜した後、ホットプレートで80℃,30分間加熱することにより膜厚90nm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、負極となるアルミニウム層を80nmの厚さに蒸着した。
最後に、ホットプレートで135℃,10分間加熱することで、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2mm×2mmであるOPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B2を用いた以外は実施例1と同様の方法で、OPV素子を作製した。
正極となる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/オゾン処理した後に、基板上に調製した陽極バッファ層用組成物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、50℃で5分間、さらに230℃で20分間加熱することで膜厚30nmのバッファ層を形成した。
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、形成したバッファ層上に溶液A2を滴下し、スピンコート法により成膜した。
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、負極となるアルミニウム層を80nmの厚さに蒸着した。
最後に、ホットプレートで90℃,10分間加熱することで、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2mm×2mmであるOPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B2を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
活性層用組成物A2の代わりに、活性層用組成物A3を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
活性層用組成物A2の代わりに、活性層用組成物A3を用い、陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B3を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B3を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B4を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物B5を用いた以外は実施例3と同様の方法で、OPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物C1を用い、230℃で20分間加熱する代わりに、150℃で20分間加熱した以外は、実施例1と同様の方法で、OPV素子を作製した。
陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物C1を用い、230℃で20分間加熱する代わりに、150℃で20分間加熱した以外は、実施例3と同様の方法で、OPV素子を作製した。
活性層用組成物A2の代わりに、活性層用組成物A3を用い、陽極バッファ層用組成物B1の代わりに、陽極バッファ層用組成物C1を用い、230℃で20分間加熱する代わりに、150℃で20分間加熱した以外は、実施例3と同様の方法で、OPV素子を作製した。
作製したOPV素子の短絡電流密度(Jsc〔mA/cm2〕)、開放電圧(Voc〔V〕)、曲線因子(FF)、及び光電変換効率(PCE〔%〕)の評価を行った。活性層用組成物に溶液A1を用いた場合(実施例1,2及び比較例1)の評価結果を表1に、溶液A2を用いた場合(実施例3,4及び比較例2)の評価結果を表2に、溶液A3を用いた場合(実施例5,6及び比較例3)の評価結果を表3に示す。また、陽極バッファ層用組成物の組成を変更した場合(実施例4,7,8及び9)の評価結果を表4に示す。
なお、光電変換効率は、光電変換効率=短絡電流密度×開放電圧×曲線因子/入射光強度という式により算出した。
このように、本発明の陽極バッファ層用組成物を用いることで、優れた光電変換特性のOPV素子を製造できることが分かる。
Claims (11)
- 式(1)で表されるアリールジアミン誘導体からなる電荷輸送性物質と、電子受容性ドーパント物質と、有機溶媒とを含むことを特徴とする有機薄膜太陽電池の陽極バッファ層用組成物。
R5~R8は、それぞれ独立して、水素原子、フェニル基、ナフチル基、ピリジル基、ピリミジニル基、ピリダジニル基、ピラジニル基、フラニル基、ピロリル基、ピラゾリル基、イミダゾリル基、チエニル基(これらの基は、ハロゲン原子、ニトロ基、シアノ基、水酸基、チオール基、リン酸基、スルホン酸基、カルボキシル基、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1~20のハロアルキル基、炭素数3~20のシクロアルキル基、炭素数6~20のビシクロアルキル基、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。)、または式(2)で表される基を表し(ただし、R5~R8の少なくとも1つは水素原子である。)、
R13及びR14は、それぞれ独立して、フェニル基、ナフチル基、アントリル基、ピリジル基、ピリミジニル基、ピリダジニル基、ピラジニル基、フラニル基、ピロリル基、ピラゾリル基、イミダゾリル基、チエニル基(これらの基は、互いに結合して環を形成してもよく、また、ハロゲン原子、ニトロ基、シアノ基、水酸基、チオール基、リン酸基、スルホン酸基、カルボキシル基、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1~20のハロアルキル基、炭素数3~20のシクロアルキル基、炭素数6~20のビシクロアルキル基、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。)〕
nは、2~5の整数を表す。} - 前記R5及びR7が、水素原子であり、
前記R6及びR8が、フェニル基である請求項1記載の有機薄膜太陽電池の陽極バッファ層用組成物。 - 前記nが、2または3である請求項1または2記載の有機薄膜太陽電池の陽極バッファ層用組成物。
- 前記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を含む請求項1~3のいずれか1項記載の有機薄膜太陽電池の陽極バッファ層用組成物。
- 前記Xが、Oを表し、前記Aが、ナフタレン環またはアントラセン環を表す請求項5記載の有機薄膜太陽電池の陽極バッファ層用組成物。
- 有機シラン化合物を含む請求項1~6のいずれか1項記載の有機薄膜太陽電池の陽極バッファ層用組成物。
- 請求項1~7のいずれか1項記載の有機薄膜太陽電池の陽極バッファ層用組成物から作製された陽極バッファ層と、それに接するように設けられた活性層とを有する有機薄膜太陽電池。
- 前記活性層が、フラーレン誘導体を含む請求項8記載の有機薄膜太陽電池。
- 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請求項8記載の有機薄膜太陽電池。
- 前記活性層が、フラーレン誘導体及び主鎖にチオフェン骨格を含むポリマーを含む請求項8記載の有機薄膜太陽電池。
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CN110073509A (zh) * | 2016-12-16 | 2019-07-30 | 日产化学株式会社 | 有机光电转换元件的空穴捕集层用组合物 |
JPWO2018110317A1 (ja) * | 2016-12-16 | 2019-10-24 | 日産化学株式会社 | 有機光電変換素子の正孔捕集層用組成物 |
JP7180379B2 (ja) | 2016-12-16 | 2022-11-30 | 日産化学株式会社 | 有機光電変換素子の正孔捕集層用組成物 |
US11563176B2 (en) | 2016-12-16 | 2023-01-24 | Nissan Chemical Corporation | Composition for hole collecting layer of organic photoelectric conversion element |
WO2018216507A1 (ja) * | 2017-05-25 | 2018-11-29 | 日産化学株式会社 | 電荷輸送性薄膜の製造方法 |
JPWO2018216507A1 (ja) * | 2017-05-25 | 2020-03-26 | 日産化学株式会社 | 電荷輸送性薄膜の製造方法 |
US20220278281A1 (en) * | 2017-05-25 | 2022-09-01 | Nissan Chemical Corporation | Method for producing charge transporting thin film |
Also Published As
Publication number | Publication date |
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US10020449B2 (en) | 2018-07-10 |
EP3082171A4 (en) | 2017-08-09 |
US20160315266A1 (en) | 2016-10-27 |
TWI623513B (zh) | 2018-05-11 |
CN105934836A (zh) | 2016-09-07 |
KR20160096637A (ko) | 2016-08-16 |
JP6520718B2 (ja) | 2019-05-29 |
EP3082171B1 (en) | 2022-04-27 |
KR102252204B1 (ko) | 2021-05-14 |
TW201538459A (zh) | 2015-10-16 |
EP3082171A1 (en) | 2016-10-19 |
JPWO2015087797A1 (ja) | 2017-03-16 |
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