JP2014170971A - 太陽電池用ポリチオフェン系活性層 - Google Patents
太陽電池用ポリチオフェン系活性層 Download PDFInfo
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- JP2014170971A JP2014170971A JP2014128099A JP2014128099A JP2014170971A JP 2014170971 A JP2014170971 A JP 2014170971A JP 2014128099 A JP2014128099 A JP 2014128099A JP 2014128099 A JP2014128099 A JP 2014128099A JP 2014170971 A JP2014170971 A JP 2014170971A
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- 229920000123 polythiophene Polymers 0.000 title description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 29
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims abstract description 4
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- 150000001875 compounds Chemical class 0.000 claims description 27
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
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- OPSFRLZQTAOAQT-UHFFFAOYSA-N [bromooxy(iodo)boranyl] hypochlorite Chemical compound ClOB(I)OBr OPSFRLZQTAOAQT-UHFFFAOYSA-N 0.000 claims description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- 125000005620 boronic acid group Chemical group 0.000 description 9
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
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- 239000007788 liquid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 239000004065 semiconductor Substances 0.000 description 6
- 238000000526 short-path distillation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 5
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 5
- 238000006619 Stille reaction Methods 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 5
- 229910003472 fullerene Inorganic materials 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003751 zinc Chemical class 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- NSYFIAVPXHGRSH-UHFFFAOYSA-N 2,5-dibromo-3-hexylthiophene Chemical compound CCCCCCC=1C=C(Br)SC=1Br NSYFIAVPXHGRSH-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000000944 Soxhlet extraction Methods 0.000 description 4
- 229910052776 Thorium Inorganic materials 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
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- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- JTGNPNLBCGBCMP-UHFFFAOYSA-N tetraoctylstannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTGNPNLBCGBCMP-UHFFFAOYSA-N 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- OIQCWAIEHVRCCG-UHFFFAOYSA-N tetrapropylstannane Chemical compound CCC[Sn](CCC)(CCC)CCC OIQCWAIEHVRCCG-UHFFFAOYSA-N 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical group O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XZARFGCHPAZJHI-UHFFFAOYSA-M tri(propan-2-yl)stannanylium;iodide Chemical compound CC(C)[Sn](I)(C(C)C)C(C)C XZARFGCHPAZJHI-UHFFFAOYSA-M 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- PZBSVWLAICUFBC-UHFFFAOYSA-N tribenzyl(phenyl)stannane Chemical compound C=1C=CC=CC=1C[Sn](C=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 PZBSVWLAICUFBC-UHFFFAOYSA-N 0.000 description 1
- JNZRDLWZFWFSBK-UHFFFAOYSA-N tribenzyltin Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)CC1=CC=CC=C1 JNZRDLWZFWFSBK-UHFFFAOYSA-N 0.000 description 1
- RKXOMPUBIQWTLT-UHFFFAOYSA-K tribromo(2-methylprop-1-enyl)stannane Chemical compound CC(C)=C[Sn](Br)(Br)Br RKXOMPUBIQWTLT-UHFFFAOYSA-K 0.000 description 1
- GOWIXKGLTIIPQR-UHFFFAOYSA-K tribromo(ethyl)stannane Chemical compound CC[Sn](Br)(Br)Br GOWIXKGLTIIPQR-UHFFFAOYSA-K 0.000 description 1
- SSGLIJVXYPSIEZ-UHFFFAOYSA-K tribromo(methyl)stannane Chemical compound C[Sn](Br)(Br)Br SSGLIJVXYPSIEZ-UHFFFAOYSA-K 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- HOXWDFOEIDECNS-UHFFFAOYSA-N tributyl(ethyl)stannane Chemical compound CCCC[Sn](CC)(CCCC)CCCC HOXWDFOEIDECNS-UHFFFAOYSA-N 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 0.000 description 1
- WKYICRPCZUOYHC-UHFFFAOYSA-K trichloro(4-ethenylhex-5-enyl)stannane Chemical compound Cl[Sn](Cl)(Cl)CCCC(C=C)C=C WKYICRPCZUOYHC-UHFFFAOYSA-K 0.000 description 1
- URNVMBADOXXKOA-UHFFFAOYSA-K trichloro(ethenyl)stannane Chemical compound Cl[Sn](Cl)(Cl)C=C URNVMBADOXXKOA-UHFFFAOYSA-K 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- XLOVMEQXRGQGAI-UHFFFAOYSA-K trichloro-(2-methylphenyl)stannane Chemical compound CC1=CC=CC=C1[Sn](Cl)(Cl)Cl XLOVMEQXRGQGAI-UHFFFAOYSA-K 0.000 description 1
- DAQURPCFGQVOHP-UHFFFAOYSA-K trichloro-(3-methylphenyl)stannane Chemical compound CC1=CC=CC([Sn](Cl)(Cl)Cl)=C1 DAQURPCFGQVOHP-UHFFFAOYSA-K 0.000 description 1
- LLMLKXBRBOGFFA-UHFFFAOYSA-K trichloro-(4-methylphenyl)stannane Chemical compound CC1=CC=C([Sn](Cl)(Cl)Cl)C=C1 LLMLKXBRBOGFFA-UHFFFAOYSA-K 0.000 description 1
- IRDOQVDUINOCMP-UHFFFAOYSA-N triethyl(2-methylpropyl)stannane Chemical compound CC[Sn](CC)(CC)CC(C)C IRDOQVDUINOCMP-UHFFFAOYSA-N 0.000 description 1
- CKGABOFCIIXWCH-UHFFFAOYSA-N triethyl(phenyl)stannane Chemical compound CC[Sn](CC)(CC)C1=CC=CC=C1 CKGABOFCIIXWCH-UHFFFAOYSA-N 0.000 description 1
- FEVOQONRVNLPJD-UHFFFAOYSA-N triethyl(propyl)stannane Chemical compound CCC[Sn](CC)(CC)CC FEVOQONRVNLPJD-UHFFFAOYSA-N 0.000 description 1
- KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
- PRFPAWZEYOPUKM-UHFFFAOYSA-M triethylstannanylium;iodide Chemical compound CC[Sn](I)(CC)CC PRFPAWZEYOPUKM-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 0.000 description 1
- YYPUUFWMUHDIRL-UHFFFAOYSA-M trimethylstannanylium;fluoride Chemical compound C[Sn](C)(C)F YYPUUFWMUHDIRL-UHFFFAOYSA-M 0.000 description 1
- XGRPNCOKLIMKBN-UHFFFAOYSA-M trimethylstannanylium;iodide Chemical compound C[Sn](C)(C)I XGRPNCOKLIMKBN-UHFFFAOYSA-M 0.000 description 1
- NDUYAGLANMHJHF-UHFFFAOYSA-N triphenyl(prop-2-enyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 NDUYAGLANMHJHF-UHFFFAOYSA-N 0.000 description 1
- CWUPWQLKYNCKBJ-UHFFFAOYSA-M tripropylstannanylium;fluoride Chemical compound CCC[Sn](F)(CCC)CCC CWUPWQLKYNCKBJ-UHFFFAOYSA-M 0.000 description 1
- MHTXEMSDIHFLFI-UHFFFAOYSA-M tripropylstannanylium;iodide Chemical compound CCC[Sn](I)(CCC)CCC MHTXEMSDIHFLFI-UHFFFAOYSA-M 0.000 description 1
- JXVWKXZIZHZZMI-UHFFFAOYSA-M tris(2-methylphenyl)stannanylium;bromide Chemical compound CC1=CC=CC=C1[Sn](Br)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C JXVWKXZIZHZZMI-UHFFFAOYSA-M 0.000 description 1
- FOWIIDZSHHTUAW-UHFFFAOYSA-M tris(2-methylphenyl)stannanylium;chloride Chemical compound CC1=CC=CC=C1[Sn](Cl)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C FOWIIDZSHHTUAW-UHFFFAOYSA-M 0.000 description 1
- FBZJTKXPWWYUSD-UHFFFAOYSA-M tris(2-methylphenyl)stannanylium;iodide Chemical compound CC1=CC=CC=C1[Sn](I)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C FBZJTKXPWWYUSD-UHFFFAOYSA-M 0.000 description 1
- YQQBSHJWYVTQTA-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;bromide Chemical compound CC(C)C[Sn](Br)(CC(C)C)CC(C)C YQQBSHJWYVTQTA-UHFFFAOYSA-M 0.000 description 1
- NHSGFFFVCFHOBS-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;chloride Chemical compound CC(C)C[Sn](Cl)(CC(C)C)CC(C)C NHSGFFFVCFHOBS-UHFFFAOYSA-M 0.000 description 1
- OUURAJKTQFMUFK-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;fluoride Chemical compound CC(C)C[Sn](F)(CC(C)C)CC(C)C OUURAJKTQFMUFK-UHFFFAOYSA-M 0.000 description 1
- WIBAFGKLTDOGDO-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;iodide Chemical compound CC(C)C[Sn](I)(CC(C)C)CC(C)C WIBAFGKLTDOGDO-UHFFFAOYSA-M 0.000 description 1
- CTBDSNCNMRAGPM-UHFFFAOYSA-M tris(3-methylphenyl)stannanylium;chloride Chemical compound CC1=CC=CC([Sn](Cl)(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 CTBDSNCNMRAGPM-UHFFFAOYSA-M 0.000 description 1
- WUDNFUZLZCDJLG-UHFFFAOYSA-M tris(4-methylphenyl)stannanylium;bromide Chemical compound C1=CC(C)=CC=C1[Sn](Br)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WUDNFUZLZCDJLG-UHFFFAOYSA-M 0.000 description 1
- XZQXAXLXLVGYRH-UHFFFAOYSA-M tris(4-methylphenyl)stannanylium;chloride Chemical compound C1=CC(C)=CC=C1[Sn](Cl)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XZQXAXLXLVGYRH-UHFFFAOYSA-M 0.000 description 1
- SKLQBHROODDCHR-UHFFFAOYSA-N trityltin Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([Sn])C1=CC=CC=C1 SKLQBHROODDCHR-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- OBYIEPMKXIBQEV-UHFFFAOYSA-N undecyl hydrogen sulfate Chemical compound CCCCCCCCCCCOS(O)(=O)=O OBYIEPMKXIBQEV-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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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
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Abstract
【解決手段】(a)下記式:
〔式中、L’は、L−C(O)O−J、L−C(O)NR’−J、L−OCO−J’、L−NR’CO−J’、L−SCO−J’、L−O−J、L−S−J、L−Se−J、L−NR’−JおよびL−CN(式中、Lは、1〜10個の炭素原子を有する直鎖または分枝アルキレン基であり、Jは、水素原子または1〜4個の炭素原子を有する直鎖若しくは分枝アルキル基であり、J’は、フェニル構造を含む若しくはフェニル構造を含まない炭素数1〜10の飽和若しくは不飽和の、直鎖若しくは分枝の基であり、R’は、水素原子または1〜4個の炭素原子を有する直鎖または分枝アルキル基である〕
で示されるモノマー単位を含むポリマー、および、(b)フラーレン誘導体のような電子受容体を含む光起電装置において使用するためのブレンド。
【選択図】なし
Description
Lは、1〜10個の炭素原子を有する直鎖または分枝アルキレン基であり、
Jは、水素原子または1〜4個の炭素原子を有する直鎖または分枝アルキル基であり、かつ、
XおよびYは、互いに独立して、水素、クロロ、ブロモ、ヨード、ボロン酸、ボロン酸エステルおよび有機スズからなる群から選択される〕
で表される化合物に関する。
で示される少なくとも1つのモノマー単位を含むポリマーに関する。
このポリマーは、ホモポリマーであっても、コポリマーであってもよい。
X’−Ar−Y’ (V)
〔式中、X’およびY’は、互いに独立して、水素、クロロ、ブロモ、ヨード、ボロン酸、ボロン酸エステルおよび有機スズからなる群から選択される〕で示されるモノマーが挙げられる。
を含む構成単位を有するコポリマー(例えば、ランダムコポリマー)であってよい。
(a)
を含んでなるモノマー単位を有するポリマー、および、
(b)フラーレン誘導体のような電子受容体
を含む、光起電デバイスにおいて使用するためのブレンドに関する。
Lは、好ましくは直鎖アルキレン基である。Lは、好ましくは2〜8個の炭素原子を有する。
で示されるコポリマーであってよい。
・基板(好ましくは、ガラスなどの透明基板)
・第1導伝層(好ましくは、ITOなどの透明導伝層)
・場合により、1つ以上の正孔輸送層
・本発明の実施態様に従うブレンドなどの活性層
・場合により、1つ以上の電子輸送層
・場合により、金属電極のような第2導伝層。
本明細書において使用する用語「電子供与体」は、別段の定めがある場合を除いて、1個以上の電子を電子受容体に対して供与できる化合物を意味する。同様に、用語「電子受容体」は、電子供与体から1個以上の電子を受容できる化合物を意味する。周知の電子受容体物質は、フラーレンおよび/またはフラーレン誘導体である。しかしながら、他の物質、例えばシアノ置換共役ポリマー〔例えば、CN−MEH−PPV(ポリ−[2−メトキシ−5−(2’−エチルヘキシルオキシ)−1,4−(1−シアノビニレン)−フェニレン])〕、ベンゾチアジアゾール含有共役ポリマー〔例えば、F8TB(ポリ(9,9’−ジオクチルフルオレンコ−ベンゾチアジアゾール)〕またはペリレン系小分子(例えば、ペリレンジカルボキシイミド誘導体)も電子受容体として考える。一実施態様において、電子受容体は、例えば[6,6]−フェニル−C61−絡酸メチルエステルなどのフラーレン誘導体であってよい。
別段の定めがある場合を除いて、全ての化学物質は商業的供給源から得られるものを使用した。ナトリウムワイヤーとベンゾフェノンによる乾燥後、THFおよびジエチルエーテルを青色になるまで蒸留した。3−ブロモチオフェンを短経路蒸留を用いて精製した。NMRスペクトルは、Varian Inova 300分光計で記録した(1Hについては300MHz、13C NMRについては75MHz、5mmプローブを使用)。重水素化CHCl3は、Cambridge Isotope Laboratories社から入手した。1Hおよび13C化学シフトは、δ=7.24ppmで、内部標準として残存CHCl3のピークを用いて、テトラメチルシラン(TMS)から低磁場側に示した。UV−Visスペクトルは、石英基板上のCHCl3溶液のドロップキャスト膜を用いて、Varian CARY 500 UV−Vis−NIR分光計(200〜800nm、600nm/分)で記録した。フーリエ変換正規外分光(FT−IR)は、公称解像度4cm−1のPerkin Elmer Spectrum One FT−IR分光計で行った。FT−IRのためのサンプルは、KBr(臭化カリウム)のペレットまたはCHCl3溶液のドロップキャスト膜であった。ガスクロマトグラフィー/質量分析(GC−MS)は、TSQ−70およびVoyager質量分析計で行った。サイズ排除クロマトグラフィー(SEC)は、0.45μm孔PTFEシリンジフィルターにより濾過した1重量%のポリマー溶液で行った。2個の混合−Bカラム(10μm、2×30cm、Polymer Labs)および屈折率検出器(Shodex)を備えたSpectraシリーズP100(Spectra Physics)ポンプ(40℃、THF中、流量1.0ml/分)を使用した。分子量分布は、ポリスチレン標準に対して測定した。トルエンを流量マーカーとして使用した。
1.3当量(18.93g、0.185モル)の無水酢酸と140mlのピリジンによる還流下、5時間、「2」(1当量、36.2g、0.143モル)を攪拌した後、「M2」を得た。塩酸を添加することにより混合物を中和し、3×100mlのジエチルエーテルにより抽出し、3×100mlの水で洗浄した。抽出物をMgSO4で乾燥させ、濾過し、蒸発させた。混合物を短経路蒸留により精製して、36.2g(113ミリモル、78%)の「M2」を得た(圧力=1.10−3mbar、温度95℃)。
M1を得るために使用した方法と類似する方法を使用して、6−ブロモメチルヘキサノエートおよび3−ブロモチオフェンからM3を得た。
6−ブロモヘキサン酸エチルエステル(20g、89ミリモル)を活性亜鉛に加えて、アルゴン雰囲気下、室温で2時間攪拌した。この亜鉛粒子を一晩落ち着かせてもよい。上澄み有機亜鉛化合物を、16.81gの3−ブロモチオフェン(103ミリモル)と0.05当量のNi(dppp)Cl2/THFの溶液に滴下した。室温で48時間、反応物を攪拌し、飽和NH4Cl溶液でクエンチした。エタノール(3×200mL)で抽出した後、有機相をMgSO4で乾燥させて、濾過した。短経路蒸留により、8.6gの6−(2,5−ジブロモ−チオフェン−3−イル)ヘキサン酸エチルエステル(38ミリモル、42%)が得られた(温度=72℃、圧力=1.10−3mbar)。
13C−NMR(75MHz、CDCl3):δ 173.4、142.4、127.8、124.8、119.6、59.8、33.9、29.8、29.6、28.4、24.4、13.8;
GC/MS 純度95%、m/z 226[M]+、181[M−OCH2CH3]+、153[M−C(O)OCH2CH3]+、139[M−CH2C(O)OCH2CH3]+、125[M−(CH2)2C(O)OCH2CH3]+、111[M−(CH2)3C(O)OCH2CH3]+、97[M−(CH2)4C(O)OCH2CH3]+;
FT−IR(NaCl, cm-1): 3104、2980、2934、2858、1733(vs)、1537、1463、1372、1299、1252、1181、1130、1096、1032、859、833、773
ポリ(3−ヘキシル−チオフェン)(P3HT)(比較例)の合成
太陽電池において比較系として使用するためのP3HTは、高立体規則性のポリ(3−アルキルチオフェン)の製造にRieke法を用いて合成した。M1溶液(1当量、10.04g、0.031モル)/80mlTHFを、−78℃で活性亜鉛に加えた。形成された有機亜鉛溶液を、0.002当量(0.035g、6.4 10−5モル)Ni(dppp)Cl2/40mlTHFの溶液に加え、不活性雰囲気下、60℃で18時間攪拌した。粗ポリマーをメタノール/2M塩酸(2/1、v/v)混合物中に沈殿させ、メタノールとヘキサンで固相抽出により精製した。濾過および乾燥前に、精製したポリマーをクロロホルムにより抽出し、メタノール中に沈降させ、3.63g(67%)の共役ポリマーを得た。
−1H NMR(300MHz、CDCl3):δ=7.00(1Harom,AcET, s)、6.96ppm(1Harom,3HT, s)、4.35ppm(2Hb,AcET, t)、3.14ppm(2Ha,AcET, t)、2.79ppm(2Ha,3HT, t),、2.05ppm (3Hc,AcET, s)、1.70ppm(2Hb,3HT, t)、1.45ppm(2Hc,3HT, m)、1.40ppm(2Hd,3HT, m)、1.35ppm(2He,3HT, m)、および0.90ppm(3Hf,3HT, t)
−UV/Vis:λmax 555nm:ショルダー 600nm;
−赤外線スペクトル:下記表1参照
−立体規則性:93%。
−収率:3.0g、52%
−UV−Vis(膜、λmax、nm)547、595sh;
−FT−IR(KBr, ν, cm−1): 2953、2925および2855(C−H)、1743(C=O)、1509および1456(C=C)、1376(CH3)、1363、1234、1037、821(C−H)
− 1H NMR(300MHz、CDCl3、δ):7.05、7.0および6.96(1H, m, Th)、4.35(2H M2, br s, β−CH2)、3.10(2H M2, br s, α−CH2)、2.78(2H, t, H−T α−CH2)、2.54(2H, br s, H−H α−CH2)、2.06(3H M2, s, CH3)、1.69−1.23(8H, m, β, γ, δおよびε−CH2)、0.89(3H, s, CH3)
−収率:2.98g、51%
−UV−Vis λmax(膜)/nm 547、595sh;
−FT−IR(KBr, ν, cm−1):3431(br, H2O)、2956、2923および2853(C−H)、1733(C=O)、1632、1455(s, C=C)、1376(CH3)、1259、1123、1002、867
− 1H NMR(300MHz、CDCl3、δ):7.11、7.06、7.01および6.96(1H, m, Th)、4.35(2H M2, br s, β−CH2)、3.10(2H M2, br s, α−CH2)、2.79(2H, t, H−T α−CH2)、2.56(2H, br s, H−H α−CH2)、2.06(3H M2, s, CH3)、1.70−1.23(8H, m, β, γ, δおよびε−CH2)、0.89(3H, m, CH3)
−1H NMR(300MHz、CDCl3):δ=7.03(1Harom,ET, s)、6.96ppm(1Harom,3HT, s)、3.94ppm(2Hb,ET, t)、3.09ppm(2Ha,ET, t)、2.79ppm(2 Ha,3HT, t)、1.70ppm(2Hb,3HT, t)、1.45ppm(2Hc,3HT, m)、1.40ppm(2Hd,3HT, m)、1.25ppm(2He,3HT, m)、および0.90ppm(3Hf,3HT, t);
−UV/Vis(膜):λmax 555nm:ショルダー 600nm;
−FT−IR(KBr, cm−1):2953および2853(C−H)、1640、1508および1455(C=C)、1376(CH3)、1292−1046および821cm−1(C−H)、723(CH3)。下記表1参照。
−立体規則性:93%
−FT−IR(KBr, cm−1):2951および2923および2853(C−H)、1639、1509および1455(C=C)、1376(CH3)、1290、1132、1042および821cm−1(C−H)、722(CH3)
−1H NMR(300MHz、CDCl3、δ):7.05、7.02および6.96(1H, m, Th)、3.96(2H, t, CH2−OH)、3.10(2H, t, α−CH2CH2−OH)、2.78(2H, t, H−T α−CH2)、2.56(2H,br s, H−H α−CH2)、1.69−1.23(8H, m, β, γ, δ, ε-CH2)、0.90(3H, t, CH3)
−立体規則性:93%
−FT−IR(KBr, cm−1):2920および2850(C−H)、1639、1508および1455(C=C)、1376(CH3)、1298、1230、1142、1038および823cm−1(C−H);
−1H NMR(300MHz、CDCl3、δ):7.02および6.96(1H, m, Th)、3.96(2H, t, CH2−OH)、3.09(2H, t, α−CH2CH2−OH)、2.78(2H, t, H−T α−CH2)、1.68−1.23(8H, m, β, γ, δ, ε-CH2)、0.90(3H, t, CH3)
−立体規則性:93%
−1H NMR(300MHz、CDCl3):δ=7.67ppm(1Hd,cin, d)、7.47ppm(2He,cin, m)、7.32ppm(2Hf,cin, m)、7.05ppm(1Hg,cin, m)、6.96ppm(1Harom,3HT and cin, s)、6.42ppm(1Hc,cin, d)、4.49ppm(2Hb,cin, t)、3.23ppm(2Ha,cin, t)、2.79ppm(2Ha,3HT, t)、1.70ppm(2Hb,3HT, m)、1.40ppm(2Hc,3HT, m)、1.35ppm(2Hd,3HT, m)、1.25ppm(2He,3HT, m)、および0.90ppm(3Hf,3HT, t);M2モノマー単位に由来する積分値は、M1モノマー単位に由来する比較積分値の約10%の相当しており、10個のモノマー単位につき1個が官能性側鎖を有していることが示された。δ=2.05ppmでP1側鎖のアセチルエーテルにおけるメチル基の消失が確認され、加水分解が完了した。完全な官能化は、異なるエステルのためP3におけるCH2−プロトンシグナルの化学シフトにおける変化によっても説明される。官能化ポリマーにおける二重結合と芳香族プロトンシグナルの出現が、側鎖におけるシンナモイルエステルの存在を裏付けている。
−UV/Vis:λmax 275nmおよび551nm:ショルダー 600nm。クロロホルム溶液からのドロップキャストポリマーフィルムの275nmにおけるλmaxは、コポリマー側鎖における桂皮酸エステルの存在に起因する。共役ポリマーの吸収領域において、600nmでのショルダーはより高い強度を有したが、鋭さははっきりとしなかった。
−赤外線スペクトル:FT−IR(KBr、cm−1):2956、2923、2853、1711、1635、1505、1449、1375、1306、1259、1158、1075、818;下記表1を参照。
−立体規則性:94%
−UV/Vis(λmax、膜)549nm:ショルダー 599nm;
−GPC(THF):Mn=25,300;Mw=47,500;D=1.9;
−FT−IR(KBr, cm−1):2956、2924、2853、1712、1635、1510、1449、1377、1307、1262、1201、1161、1090、1021、804;
−1H NMR(300MHz、CDCl3、δ):7.70および7.64(d, 1H, C=CH−pH)、7.46(m, 2H, CHPh)、7.33(m, 2H, CHPh)、7.12−6.96(m, HThおよびHph)、6.44および6.39(d, 1H, COCH=C)、4.48(t, 2H, CH2O)、3.21(t, 2H, α−CH2)、2.77(t, 2H, H−T α−CH2 3−HT)および2.56(α−CH2 3−HT)、1.67−1.31(m, 6H, γ, δ, ε−CH2 3−HT)、0.88(t, 3H, CH3)
−立体規則性:93%
−UV/Vis(λmax、膜)521nm;
−GPC(THF):Mn=19,800;Mw=40,300;D=2.0;
−FT−IR(KBr, cm−1):3060、2954、2926、2855、1714、1637、1511、1495、1450、1378、1327、1309、1282、1202、1162、1071、978、862、823、766;
−1H NMR(300MHz、CDCl3、δ):7.68および7.63(d, 1H, C=CH−pH)、7.46(m, 2H, CHPh)、7.32(m, 2H, CHPh)、7.12−6.96(m, HThおよびHph)、6.43および6.38(d,1H, COCH=C)、4.47(t, 2H, CH2O)、3.21(t, 2H, α−CH2)、2.76(t, 2H, H−T α−CH2 3−HT)および2.56(α−CH2 3−HT)、1.67−1.23(m, 2H, β−CH2 3−HT)、1.30−1.23(m, 6H, γ, δ, ε−CH2 3−HT)、0.88(t, 3H, CH3)
合成は、下記式に従って進み、式(IX)〔式中、L’はL−NR’CO−J’であり、Lはエチレンであり、R’はHであり、J’はシンナモイルである〕で示されるモノマー由来の繰り返し単位を有するコポリマーを提供する。
合成は、下記式に従って進み、式(IX)〔式中、L’はL−SCO−J’であり、Lはエチレンであり、J’はシンナモイルである〕で示されるモノマー由来の繰り返し単位を有するコポリマーを提供する。
−収率:3.77g、74%
−UV−Vis λmax(膜)/nm 555nm、602sh;
−FT−IR(膜, ν, cm−1):3053、2953、2928および2854(C−H)、1738(C=O)、1563、1509および1455(C=C)、1376(CH3)、1260(w)、1179および820(C−H)、726(CH3)
−1H NMR(300MHz、CDCl3、δ):6.96(1H, s, Th)、4.10(2H M3, q, OCH2)、2.79(2H, t, H−T α−CH2)、2.56(2H, s, H−H α−CH2)、2.31(2H M3, t, CH2COOEt)、1.69(2H, br s, β−CH2およびM3)、1.48−1.20(10H, m, γ, δ, ε−CH2およびγ, δ CH2 M3)、0.90(6H, t, CH3 M1およびM3)
−GPC(THF):Mw=56,700;D=1.9;
−立体規則性:93%
−収率:4.51g、61.5%
−UV−Vis λmax(膜)/nm 550nm、600sh;
−FT−IR(膜, ν, cm−1):2926および2855(C−H)、1736(C=O)、1508および1458(C=C)、1375(CH3)、1227、1178および824(C−H)、760(CH3);
−1H NMR(300MHz、CDCl3、δ):6.96(1H, s, Th)、4.10(2H M3, q, OCH2)、2.79(2H, br s, H−T α−CH2)、2.56(2H, s, H−H α−CH2)、2.31(2H M3, t, CH2COOEt)、1.69(4H, m, β−CH2 M1およびM3)、1.54−1.20(10H, m, γ, δ, ε−CH2およびγ, δ−CH2 M3)、0.89(6H, t, CH3 M1およびM3)
−GPC(THF):Mw=90,500;D=2.3;
−立体規則性:90%
−収率:4.14g、53%
−UV−Vis λmax(膜)/nm 550nm、604sh;
−FT−IR(膜, ν, cm−1):3432(br, COOH)、2956(C−H)、1733(C=O)、1631および1454(C=C)、1259、1129、1002および867cm−1(C−H)
−1H NMR(300MHz、CDCl3、δ):6.96(1H, s, Ar H)、4.10(2H M3, q, OCH2)、2.79(2H, t, H−T α−CH2)、2.54(2H, H−H α−CH2)、2.31(2H M3, t, CH2COOEt)、1.69(4H, m, β−CH2 M1およびM3)、1.50−1.20(10H, m, γ, δ, ε−CH2 M1およびγ, δ−CH2 M3)、0.87(6H, t, CH3 M1およびM3)
−GPC(THF):Mw=119,500;D=2.7;
−立体規則性:89%
全てのポリマー:PCBMのブレンドは、1/1の比率(w/w)で製造した。PCBMは、下記化学式を有する:
本発明の好ましい態様は、以下を包含する。
[1]構造式(I):
Lは、1〜10個の炭素原子を有する直鎖または分枝アルキレン基であり、
Jは、水素原子または1〜4個の炭素原子を有する直鎖または分枝アルキル基であり、かつ、
XおよびYは、互いに独立して、水素、クロロ、ブロモ、ヨード、ボロン酸、ボロン酸エステルおよび有機スズからなる群から選択される〕
で表される化合物。
[2]式(IV):
Lは、1〜10個の炭素原子を有する直鎖または分枝アルキレン基であり、
Jは、水素原子または1〜4個の炭素原子を有する直鎖若しくは分枝アルキル基である〕
で示されるモノマー単位を含むポリマー。
[3]式(IV)のモノマー単位と少なくとも1つのコモノマーを含んでなるランダムコポリマー、交互コポリマーまたはブロックコポリマーである[2]に記載のポリマー。
[4]前記少なくとも1つのコモノマーが単素環芳香族基または複素環芳香族基である[3]に記載のコポリマー。
[5]前記コモノマーが、下記式:
で示される[4]に記載のコポリマー。
[6]前記コポリマーが、3:2〜1:49、好ましくは3:2〜1:19、より好ましくは1:4〜1:19の比率で、式(IV)で表されるモノマー単位とコモノマーを含む[3]〜[5]のいずれかに記載のコポリマー。
[7][3]に記載のポリマーの製造方法であって、
[1]に記載の化合物、および場合により式:
で示されるコモノマーを還元カップリングにより重合することを含む方法。
[8](a)
を含んでなるモノマー単位を有するポリマー、および、
(b)フラーレン誘導体のような電子受容体
を含む、光起電デバイスにおいて使用するためのブレンド。
[9]前記ポリマーが、式(IV)のモノマー単位と少なくとも1つのコモノマーを含んでなるランダムコポリマー、交互コポリマーまたはブロックコポリマーである、[8]に記載のブレンド。
[10]前記少なくとも1つのコモノマーが単素環芳香族基または複素環芳香族基である[9]に記載のブレンド。
[11]前記コモノマーが、下記式:
で示される、[10]に記載のブレンド。
[12]前記コポリマーが、3:2〜1:49、好ましくは3:2〜1:19、より好ましくは1:4〜1:19の比率で、式(IV)で表されるモノマー単位とコモノマーを含む[9]〜[11]のいずれかに記載のブレンド。
[13]前記ポリマーが[2]〜[6]のいずれかに記載のポリマーである、[8]に記載のブレンド。
[14][8]〜[13]のいずれかに記載のブレンドを含んでなる光電子デバイス。
[15]陽極、陰極および[7]〜[11]のいずれかに記載のブレンドを含んでなり、陽極または陰極の少なくとも一方が、少なくとも一部の太陽スペクトルに対して透過的な光起電デバイスである、[14]に記載の光電子デバイス。
[16]
を含んでなるモノマー単位を有するポリマーの、バルクヘテロ接合太陽電池の形態安定化のための使用。
Claims (16)
- 式(IV)のモノマー単位と少なくとも1つのコモノマーを含んでなるランダムコポリマー、交互コポリマーまたはブロックコポリマーである請求項2に記載のポリマー。
- 前記少なくとも1つのコモノマーが単素環芳香族基または複素環芳香族基である請求項3に記載のコポリマー。
- 前記コポリマーが、3:2〜1:49、好ましくは3:2〜1:19、より好ましくは1:4〜1:19の比率で、式(IV)で表されるモノマー単位とコモノマーを含む請求項3〜5のいずれかに記載のコポリマー。
- (a)
を含んでなるモノマー単位を有するポリマー、および、
(b)フラーレン誘導体のような電子受容体
を含む、光起電デバイスにおいて使用するためのブレンド。 - 前記ポリマーが、式(IV)のモノマー単位と少なくとも1つのコモノマーを含んでなるランダムコポリマー、交互コポリマーまたはブロックコポリマーである、請求項8に記載のブレンド。
- 前記少なくとも1つのコモノマーが単素環芳香族基または複素環芳香族基である請求項9に記載のブレンド。
- 前記コポリマーが、3:2〜1:49、好ましくは3:2〜1:19、より好ましくは1:4〜1:19の比率で、式(IV)で表されるモノマー単位とコモノマーを含む請求項9〜11のいずれかに記載のブレンド。
- 前記ポリマーが請求項2〜6のいずれかに記載のポリマーである、請求項8に記載のブレンド。
- 請求項8〜13のいずれかに記載のブレンドを含んでなる光電子デバイス。
- 陽極、陰極および請求項7〜11のいずれかに記載のブレンドを含んでなり、陽極または陰極の少なくとも一方が、少なくとも一部の太陽スペクトルに対して透過的な光起電デバイスである、請求項14に記載の光電子デバイス。
-
を含んでなるモノマー単位を有するポリマーの、バルクヘテロ接合太陽電池の形態安定化のための使用。
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JP2008515195A (ja) * | 2004-09-24 | 2008-05-08 | プレックストロニクス インコーポレーティッド | 光電池におけるヘテロ原子位置規則性ポリ(3−置換チオフェン) |
WO2009056496A1 (en) * | 2007-10-31 | 2009-05-07 | Basf Se | Process for preparation of regioregular conducting block copolymers |
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JP2008515195A (ja) * | 2004-09-24 | 2008-05-08 | プレックストロニクス インコーポレーティッド | 光電池におけるヘテロ原子位置規則性ポリ(3−置換チオフェン) |
WO2009056496A1 (en) * | 2007-10-31 | 2009-05-07 | Basf Se | Process for preparation of regioregular conducting block copolymers |
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