TWI656124B - 苉衍生物、光電轉換材料及光電轉換元件 - Google Patents
苉衍生物、光電轉換材料及光電轉換元件 Download PDFInfo
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- TWI656124B TWI656124B TW104134243A TW104134243A TWI656124B TW I656124 B TWI656124 B TW I656124B TW 104134243 A TW104134243 A TW 104134243A TW 104134243 A TW104134243 A TW 104134243A TW I656124 B TWI656124 B TW I656124B
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- substituted
- photoelectric conversion
- hydrocarbon group
- unsubstituted hydrocarbon
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 92
- 239000000463 material Substances 0.000 title claims abstract description 61
- 239000004065 semiconductor Substances 0.000 claims abstract description 31
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims description 35
- -1 nitro, hydroxyl Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
- 239000010408 film Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 35
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- 150000002220 fluorenes Chemical class 0.000 description 24
- 238000000034 method Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 238000012546 transfer Methods 0.000 description 15
- CFRRRFIZJNHSLM-UHFFFAOYSA-N 8,15-dithiapentacyclo[11.7.0.02,10.05,9.014,18]icosa-1(13),2(10),3,5(9),6,11,14(18),16,19-nonaene Chemical compound S1C=CC2=C1C1=C(C=C2)C2=C(C=C1)C1=C(C=CS1)C=C2 CFRRRFIZJNHSLM-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 5
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 229910003472 fullerene Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexanol Substances CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
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- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical group CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical group C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical group CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
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- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- 238000000944 Soxhlet extraction Methods 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000231 atomic layer deposition Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
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- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
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- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical group CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
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- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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Abstract
本發明提供一種容易製造且於高分子骨架內具有高度平面性之p型有機半導體材料、及使用有此種p型有機半導體材料之具有高度光電轉換效率之光電轉換層、光電轉換元件及有機薄膜太陽電池,具體而言,提供一種具有至少1個下述通式(1)所表示之結構單元之苉衍生物、及含有作為(A)p型有機半導體材料之上述苉衍生物及(B)n型有機半導體材料而成之光電轉換材料。通式(1)之詳情如本說明書所記載。
Description
本發明係關於一種具有特定構造之新穎p型有機半導體材料、光電轉換材料及使用其之光電轉換元件。
近年來,業界積極研究可持續利用,不缺乏資源,且環境污染較小之太陽電池(太陽光發電)。太陽電池大致分為Si系或非Si系之無機系太陽電池與色素增感型或有機薄膜型之有機系太陽電池。無機系太陽電池總體而言光電轉換效率較高,但需要高真空,或需要高溫熱處理,故而存在製造成本變高之缺點。另一方面,有機系太陽電池能夠利用塗佈法或印刷法等進行製膜,故而製造成本較低,能夠大面積製膜。又,亦可列舉與無機系太陽電池相比減輕元件之優點。尤其是有機薄膜型之太陽電池,其印刷法優異,亦容易製膜為膜等,故而亦容易製造軟性太陽電池。
然而,大多有機系太陽電池之光電轉換效率較低,故而高光電轉換效率化成為課題。
當前,作為獲得有機薄膜型之太陽電池之高度光電轉換效率之材料,可列舉包含p型有機半導體材料之P3HT[聚(3-己基噻吩)]與n型有機半導體材料之PCBM[[6,6]-苯基-C61-丁酸甲酯]之混合材料之塊材異質接合(參考非專利文獻1等)。又,作為p型有機半導體材料,亦存在使用稠五苯等低分子化合物之情形,一般認為高分子型材料適於利用塗佈製造元件,容易進行低成本化或大畫面化。
作為p型有機半導體材料所要求之特徵,可列舉材料中具有平面性較高之π共軛平面。其原因在於可期待較高之π-π相互作用或較高之載子傳輸效率,結果可提供較高之光電動勢。
專利文獻1~3中揭示有關於高分子型之p型有機半導體之內容。
專利文獻1:美國專利申請公開2008/0083455號公報
專利文獻2:日本專利特開2009-158921號公報
專利文獻3:日本專利特表2011-116962號公報
非專利文獻1:F. Padinger, et al., Adv. Funct. Mater., 13, 85 (2003)
因此,本發明之目的在於提供一種容易製造,且於高分子骨架內具有高度平面性之p型有機半導體材料。
又,本發明之目的在於提供一種使用上述p型有機半導體材料而具有高度光電轉換效率之光電轉換層、光電轉換元件及有機薄膜太陽電池。
本發明者等人反覆進行努力研究,結果發現,若將下述通式(1)所表示之苉衍生物用作p型有機半導體材料,則可容易地製造光電轉換層。進一步繼續研究之結果,發現具有該光電轉換層之光電轉換元件顯示較高之載子移動率,可解決上述問題。
本發明係基於上述見解而成者,提供一種具有至少1個下述通式(1)所表示之結構單元之新穎苉衍生物(以下亦稱為苉衍生物)。
(式中,A1及A2分別獨立表示單環,R1、R2、R3、R4、R5及R6分別獨立表示氫原子、鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-SiR7R8R9、-NR10R11基、或具有取代基或未經取代之烴基,R1、R2、R3、R4、R5及R6之至少一者不為氫原子,R7、R8、R9、R10或R11分別獨立表示氫原子或具有取代基或未經取代之烴基)
又,本發明提供一種含有作為(A)p型有機半導體材料之上述苉衍生物、及(B)n型有機半導體材料而成之光電轉換材料。
又,本發明提供一種包含(A)含有至少一種苉衍生物之p型有機半導體材料、及(B)n型有機半導體材料而成之光電轉換材料。
又,本發明提供一種將上述光電轉換材料進行製膜而獲得之光電轉換層。
又,本發明提供一種具有上述光電轉換層而成之光電轉換元件。
又,本發明提供一種具有上述光電轉換元件而成之有機薄膜太陽電池。
根據本發明,可提供一種作為有機半導體材料有用之新穎苉衍
生物。若使用含有該化合物之本發明之光電轉換材料,則可藉由較高之載子移動率實現元件之高性能化。
1‧‧‧支持體
2‧‧‧電極
3‧‧‧電荷轉移層
4‧‧‧光電轉換層
5‧‧‧電極
6‧‧‧電荷轉移層
圖1(a)係表示本發明之光電轉換元件之構成之一例之剖視圖,圖1(b)係表示本發明之光電轉換元件之構成之另一例之剖視圖,圖1(c)係表示本發明之光電轉換元件之構成之另一例之剖視圖。
以下,基於較佳之實施形態對本發明之苉衍生物、光電轉換材料、光電轉換層、光電轉換元件及有機薄膜太陽電池進行詳細說明。
苉衍生物為具有至少1個上述通式(1)所表示之結構單元之化合物。再者,上述通式(1)中之*意為該等式所表示之基於*部分與鄰接之基鍵結(以下相同)。
上述通式(1)中之A1及A2所表示之單環並無特別限定,較佳為芳香族性之單環,作為具體之例,可列舉苯環、呋喃環、噻吩環、硒吩環、碲吩環、噻唑環、異噻唑環、唑環、異唑環、吡啶環、吡環、嘧啶環、嗒環、吡咯環、咪唑環、吡唑環等。其中,包含硫原子、硒原子、碲原子之雜環可提高元件之特性故而較佳。
上述通式(1)中之R1、R2、R3、R4、R5或R6分別獨立表示氫原子、鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-SiR7R8R9、-NR10R11基、具有取代基或未經取代之烴基,R1、R2、R3、R4、R5及R6之至少一者不為氫原子。
R7、R8、R9、R10或R11分別獨立表示氫原子或具有取代基或未經取代之烴基。
上述通式(1)中,作為鹵素原子,可列舉氟、氯、溴、碘等,作為上述烴基,可列舉芳香族烴基、經脂肪族烴取代之芳香族
烴基、脂肪族烴基,碳原子數較佳為1~40,尤佳為4~22。
作為上述芳香族烴基,例如可列舉苯基、萘基、環己基苯基、聯苯基、聯三苯基、茀基、噻吩基苯基、呋喃基苯基、2'-苯基-丙基苯基、苄基、萘基甲基等,作為上述脂肪族烴基,例如可列舉甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、己基、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、壬基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基等直鏈、支鏈及環狀之烷基,該等脂肪族烴基亦可被-O-、-COO-、-OCO-、-CO-、-S-、-SO-、-SO2-、-NR15-、-HC=CH-或-C≡C-中斷(再者,該中斷亦可中斷脂肪族烴基進行鍵結之部分),R15表示具有取代基或未經取代之烴基,作為具有取代基或未經取代之烴基,可列舉與上述相同之基,其中較佳為全氟烷基。
作為上述經脂肪族烴取代之芳香族烴基,可列舉經上述脂肪族烴基取代之苯基、萘基、苄基等。
作為可對該等烴基進行取代之基,可列舉鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR'R"基等,R'及R"表示具有取代基或未經取代之烴基,作為具有取代基或未經取代之烴基,可列舉與上述相同之基。
苉衍生物之中,具有2個以上且100個以下之上述通式(1)所表示之結構單元者之製膜性優異故而較佳。又,苉衍生物亦可具有上述通式(1)所表示之結構單元以外之結構單元(以下,亦稱為其他結構單元)。於苉衍生物包含其他結構單元之情形時,上述通式(1)之結構單元較佳為5~100莫耳%,進而較佳為10~90莫耳%,尤佳為20~80莫耳%。
上述通式(1)所表示之苉衍生物之中,下述通式(1-1)或(1-2)所表
示者容易製造故而較佳。
(式中,A3及A4表示上述A1及A2中例示內之作為6員環者,A5及A6表示上述A1及A2中例示內之作為5員環者,R1、R2、R3、R4、R5或R6與上述通式(1)相同,R1、R2、R3、R4、R5及R6之至少一者不為氫原子)
具有上述通式(1-1)及(1-2)所表示之構成之苉衍生物之中,上述通式(1-1)中之A3及A4為同一6員環者、或上述通式(1-2)中之A5及A6為同一5員環者因更容易製造故而較佳。
作為其他結構單元,只要為π共軛之基則並無特別限定,可列舉選自下述群Y或群Z之結構單元為例,就材料之耐久性、耐光性之方面而言,選自(Y-2)、(Y-3)、(Y-4)或群Z之結構單元較佳。
(式中,X1及X4表示S、O或NR12,k表示1~4之整數,R12表示經取代或未經取代之烴基,群Y所表示之結構單元中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR13R14基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R13及R14表示經取代或未經取代之烴基)
(式中,X2表示S或NR15,X3表示S、NR15、CR16R17或SiR16R17,
X5表示S、O或NR15,R15、R16及R17表示經取代或未經取代之烴基,群Z所表示之結構單元中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR18R19基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R18及R19表示經取代或未經取代之烴基)
作為可取代群Y或群Z所表示之結構單元中之氫原子之烴基,及群Y中之表示X1及X4之NR12、群Z中之表示R15、X2及X5之NR15、及表示X3之NR15、CR16R17、SiR16R17之R12、R15、R16及R17所表示之經取代或未經取代之烴基,可列舉與上述通式(1)中之經取代或未經取代之烴基相同之基。
於苉衍生物包含上述群Y或群Z之結構單元之情形時,苉衍生物表示為下述通式(1'),該通式(1')中之o、p或q個各結構單元之排列並無特別限定,均發揮本發明之效果。又,作為各結構單元之較佳比率,將式(1)之結構單元之o設為1時,群Y或群Z之結構單元之p或q為1~10。更佳之p之值就長波長區域之較高吸光效率之方面而言,為0~8,進而較佳為1~5。又,更佳之q之值就長波長區域之較高吸光效率之方面而言,為0~2,進而較佳為1~2,尤佳為1。
(式中之氫原子亦可與上述通式(1)同樣地被取代,Y表示選自上述群Y之基,Z表示選自上述群Z之基,
o表示1以上且1000以下,p及q表示0以上且1000以下)
又,作為苉衍生物之較佳例,可列舉下述通式(2)所表示之化合物,作為更佳例,可列舉下述通式(2-1)或(2-2)所表示之化合物。
(式中,A1、A2、R1、R2、R3、R4、R5及R6表示與上述式(1)相同之基,R1、R2、R3、R4、R5及R6之至少一者不為氫原子,Y1及Y2為單鍵或組合1~5個選自下述(Y-1)~(Y-8)之基連結而成之基,Z1表示單鍵或選自下述(Z-1)~(Z-21)之基,n表示1以上且1000以下之整數)
(式中,X1及X4表示S、O或NR12,k表示1~4之整數,R12表示經取代或未經取代之烴基,(Y-1)~(Y-4)及(Y-6)~(Y-8)所表示之基中之氫原子可被取代為鹵
素原子、氰基、硝基、羥基、羧基、硫醇基、-NR13R14基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R13及R14表示經取代或未經取代之烴基)
(式中,X2表示S或NR15,X3表示S、NR15、CR16R17或SiR16R17,X5表示S、O或NR15,R15、R16及R17表示經取代或未經取代之烴基,(Z-1)~(Z-21)所表示之基中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、
硫醇基、-NR18R19基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R18及R19表示經取代或未經取代之烴基)
(式中,A1、A2、R1、R2、R3、R4、R5及R6表示與上述式(1)相同之基,A3及A4與上述式(1-1)相同,A5及A6與上述式(1-2)相同,Y1、Y2、Z1及n與上述式(2)相同,R1、R2、R3、R4、R5及R6之至少一者不為氫原子)
上述通式(2)、(2-1)或(2-2)所表示之化合物中,Y1、Y2或Z1之至少一者不為單鍵之化合物因作為光電轉換元件之特性優異,故而較佳。
又,通式(2)、(2-1)或(2-2)所表示之化合物中,R1、R2、R3、R4、R5及R6之至少一者為氫原子以外之取代基,R1、R2、R3、R4、R5及R6之取代基之種類並無特別限定,均發揮本發明之效果,較佳為如下化合物:R1、R2、R3、R4、R5及R6之至少一者表示碳原子數1~30之未經取代之烷基、或碳原子數1~30之經取代之烷基,該未經取代之烷基及經取代之烷基中之亞甲基可表示-CH=CH-或-C≡C-,可對該烷基進行取代之取代基為烷氧基、烷硫基、芳基、芳氧基、芳硫基、
雜環基、醯基、醯氧基、胺基、磺醯基、羧基、氰基、磺基、羥基、巰基、亞胺基、鹵素原子;更佳為碳原子數1~30之未經取代之烷基、或碳原子數1~30之經取代之烷基;尤佳為碳原子數10~20之未經取代之烷基、或碳原子數10~20之經取代之烷基。
又,R1、R2、R3、R4、R5及R6中,氫原子以外之取代基之位置並無特別限定,均發揮本發明之效果,較佳為R1、R3、R4及R6,更佳為R1及R6。
作為苉衍生物之具體例,可列舉下述No.1~No.17,但不特別限定於該等。再者,下述式中之R1、R2、R3、R4、R5及R6為與上述通式(1)中相同之基,n表示與上述通式(2)中相同之數,Hex表示己基,2-EH表示2-乙基己基,2-HD表示2-己基癸基、2-OD表示2-辛基十二烷基。
本發明之苉衍生物之製造方法均無限制,可藉由利用周知一般反應之方法而獲得。作為上述通式(2)所表示之苉衍生物之製造方法
之一例,可藉由根據下述之反應式,使自苉衍生物(3)反應而得之雙三甲基錫體(4)與藉由已知之合成法而獲得之鹵化π共軛基(5)進行縮聚反應,而獲得本發明之苉衍生物(2)。
(式中,A1、A2、R1、R2、R3、R4、R5、R6、Y1、Y2、Z1、n表示與上述通式(2)所說明者相同之基)
本發明之苉衍生物除適宜作為有機半導體材料外,亦可用於抗氧化劑等用途。
本發明之光電轉換材料係包含(A)含有至少一種苉衍生物之p型有機半導體材料、及(B)n型有機半導體材料者。
作為(A)p型有機半導體材料,含有至少一種上述本發明之苉衍生物即可,可併用其他公知材料。關於本發明之苉衍生物,可適宜地應用上述內容。作為公知材料,例如可列舉酞菁系顏料、靛藍或硫靛藍系顏料、喹吖酮系顏料、三芳基甲烷衍生物、三芳基胺衍生物、唑衍生物、腙衍生物、茋衍生物、吡唑啉衍生物、聚矽烷衍生物、聚苯乙炔及其衍生物(例如,聚[2-甲氧基-5-(2-乙基己氧基)-1,4-苯乙炔]:MEH-PPV、聚[2-甲氧基-5-(3',7'-二甲基辛氧基)-1,4-苯乙炔])、聚噻吩及其衍生物(例如,聚(3-十二烷基噻吩)、聚(3-己基噻吩):P3HT、
聚(3-辛基噻吩))、聚-N-乙烯咔唑衍生物等。
於使用其他公知材料作為(A)p型有機半導體材料之情形時,苉衍生物之含量於(A)p型有機半導體材料中較佳為1~99質量%,更佳為1~80質量%。
作為(B)n型有機半導體材料,可使用苝系顏料、芘系顏料、多環醌系顏料、偶氮系顏料、C60富勒烯或C70富勒烯及其衍生物等,又,亦可使用有機金屬錯合物[例如,三(8-羥基喹啉)鋁、雙(10-苯并[h]羥基喹啉)鈹、5-羥基黃酮之鈹鹽、5-羥基黃酮之鋁鹽]、二唑衍生物[例如,1,3-雙[5'-(對第三丁基苯基)-1,3,4-二唑-2'-基]苯]、三唑衍生物[例如,3-(4'-第三丁基苯基)-4-苯基-5-(4"-聯苯)-1,2,4-三唑]、啡啉衍生物[例如,2,9-二甲基-4,7-聯苯基-1,10-啡啉(BCP,bathocuproin)]、三衍生物、喹啉衍生物、喹啉衍生物、二苯基苯醌衍生物、硝基取代茀酮衍生物、二氧化噻喃衍生物等。(B)n型有機半導體材料中,就作為n型材料,具有較高之載子移動率、及/或電荷分離效率較高之方面而言,較佳為C60富勒烯或C70富勒烯及其衍生物。再者,例中作為n型有機半導體材料所列舉之化合物可單獨使用,或亦可併用複數種。
作為上述C60富勒烯或C70富勒烯及其衍生物,列舉以下C1~C6之化合物為例,其中,就電子能階之整合性優異,容易獲得之方面而言,較佳為使用C1之PCBM(苯基-C61-丁酸甲酯)。
[化13]
本發明之光電轉換材料中,(A)成分與(B)成分之重量比率(前者:後者)為10:90~90:10,較佳為10:90~70:30,進而較佳為20:80~50:50。
又,本發明之光電轉換材料視需要亦可含有一種或兩種以上之溶劑。
作為上述溶劑,只要為能夠溶解或分散(A)成分及(B)成分者,則並無特別限定,例如可列舉水、醇系溶劑、二醇系溶劑、酮系溶劑、酯系溶劑、醚系溶劑、脂肪族或酯環族烴系溶劑、芳香族烴系溶劑、具有氰基之烴溶劑、鹵化烴系溶劑、其他溶劑等。使用溶劑之光電轉換材料可作為塗佈液使用。
作為上述醇系溶劑,例如可列舉甲醇、乙醇、丙醇、異丙醇、1-丁醇、異丁醇、2-丁醇、第三丁醇、戊醇、異戊醇、2-戊醇、新戊醇、第三戊醇、己醇、2-己醇、庚醇、2-庚醇、辛醇、2-乙基己醇、2-辛醇、環戊醇、環己醇、環庚醇、甲基環戊醇、甲基環己醇、甲基環庚醇、苄醇、乙二醇單甲醚、乙二醇單乙醚、丙二醇單甲醚、丙二
醇單乙醚、二乙二醇單甲醚、二乙二醇單乙醚、三乙二醇單甲醚、三乙二醇單乙醚、2-(N,N-二甲胺基)乙醇、3(N,N-二甲胺基)丙醇等。
作為上述二醇系溶劑,例如可列舉乙二醇、丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、新戊二醇、異戊二醇(3-甲基-1,3-丁二醇)、1,2-己二醇、1,6-己二醇、3-甲基-1,5-戊二醇、1,2-辛二醇、辛二醇(2-乙基-1,3-己二醇)、2-丁基-2-乙基-1,3-丙二醇、2,5-二甲基-2,5-己二醇、1,2-環己二醇、1,4-環己二醇、1,4-環己烷二甲醇等。
作為上述酮系溶劑,例如可列舉丙酮、甲基乙基酮、甲基異丙基酮、甲基丁基酮、甲基異丁基酮、甲基戊基酮、甲基己基酮、乙基丁基酮、二乙酮、二丙酮、二異丁酮、甲基戊基酮、環己酮、甲基環己酮等。
作為上述酯系溶劑,例如可列舉甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯、乙酸異丙酯、乙酸丁酯、乙酸異丁酯、乙酸第二丁酯、乙酸第三丁酯、乙酸戊酯、乙酸異戊酯、乙酸第三戊酯、乙酸苯酯、丙酸甲酯、丙酸乙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丙酸第二丁酯、丙酸第三丁酯、丙酸戊酯、丙酸異戊酯、丙酸第三戊酯、丙酸苯酯、2-乙基己酸甲酯、2-乙基己酸乙酯、2-乙基己酸丙酯、2-乙基己酸異丙酯、2-乙基己酸丁酯、乳酸甲酯、乳酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸乙酯、乙二醇單甲醚乙酸酯、二乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單異丙醚乙酸酯、乙二醇單丁醚乙酸酯、乙二醇單第二丁醚乙酸酯、乙二醇單異丁醚乙酸酯、乙二醇單第三丁醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單異丙醚乙酸酯、丙二醇單丁醚乙酸酯、丙二醇單第二丁醚乙酸酯、丙二醇單異丁醚乙酸酯、丙二醇單第三丁
醚乙酸酯、丁二醇單甲醚乙酸酯、丁二醇單乙醚乙酸酯、丁二醇單丙醚乙酸酯、丁二醇單異丙醚乙酸酯、丁二醇單丁醚乙酸酯、丁二醇單第二丁醚乙酸酯、丁二醇單異丁醚乙酸酯、丁二醇單第三丁醚乙酸酯、乙醯乙酸甲酯、乙醯乙酸乙酯、側氧丁酸甲酯、側氧丁酸乙酯、γ-內酯、丙二酸二甲酯、丁二酸二甲酯、丙二醇二乙酸酯、δ-內酯等。
作為上述醚系溶劑,例如可列舉四氫呋喃、四氫吡喃、啉、乙二醇二甲醚、二乙二醇二甲醚、二丙二醇二甲醚、三乙二醇二甲醚、二丁醚、二乙醚、二烷等。
作為上述脂肪族或酯環族烴系溶劑,例如可列舉戊烷、己烷、環己烷、甲基環己烷、二甲基環己烷、乙基環己烷、庚烷、辛烷、十氫萘、溶劑石腦油、松節油、D-檸檬烯、蒎烯、礦油精、Swazol # 310(COSMO MATSUYAMA OIL(股)、Solvesso # 100(Exxon Chemical(股))等。
作為上述芳香族烴系溶劑,例如可列舉苯、甲苯、乙基苯、二甲苯、均三甲苯、二乙基苯、異丙苯、異丁基苯、異丙基甲苯、四氫萘等。
作為上述具有氰基之烴溶劑,例如可列舉乙腈、1-氰基丙烷、1-氰基丁烷、1-氰基己烷、氰基環己烷、氰基苯、1,3-二氰基丙烷、1,4-二氰基丁烷、1,6-二氰基己烷、1,4-二氰基環己烷、1,4-二氰基苯等。
作為上述鹵化烴系溶劑,例如可列舉四氯化碳、氯仿、二氯甲烷、三氯乙烯、氯苯、二氯苯、三氯苯等。
作為上述其他有機溶劑,例如可列舉N-甲基-2-吡咯啶酮、二甲基亞碸、二甲基甲醯胺、苯胺、三乙胺、吡啶、二硫化碳等。
該等之中,作為較佳之溶劑,可列舉氯仿、二氯甲烷、甲苯、
二甲苯、氯苯、二氯苯、三氯苯等。
於使本發明之光電轉換材料含有上述溶劑之情形時,其含量只要不阻礙使用該光電轉換材料之光電轉換層之形成則並無特別限定,較理想為例如將溶劑設為100重量份時,(A)成分及(B)成分之總量較佳為自0.1~20重量份之範圍適宜地選擇,進而較佳為1~10重量份,尤佳為自3~7重量份之範圍選擇。
其次,對本發明之光電轉換層進行說明。本發明之光電轉換層係將本發明之光電轉換材料進行製膜而獲得。關於製膜方法並無特別限定,例如,可列舉如下方法:藉由蒸鍍法、物理氣相沈積法(PVD)、化學氣相沈積法(CVD)、原子層沈積法(ALD)、原子層磊晶法(ALE)、分子束磊晶法(MBE)、氣相磊晶法(VPE)、濺鍍法、電漿聚合法等乾式製程;浸漬塗佈法、澆鑄法、氣刀塗佈法、淋幕式塗佈法、輥式塗佈法、線棒塗佈法、凹版塗佈法、旋轉塗佈法、LB(Langmuir-Blodgett,朗繆爾-布洛傑特)法、平版印刷法、網版印刷法、軟版印刷法、分注器印刷法、噴墨法、擠壓塗佈法等濕式製程,於支持體上形成塗膜。
上述光電轉換層之膜厚並無特別限定,一般較佳為設定為5nm~5μm左右,亦可進行退火等加熱處理。
上述光電轉換層可用於混合存在p型與n型之有機半導體材料之元件,除作為較佳之實施形態之有機塊材異質接合元件外,亦用於超階層奈米構造接合元件、混合異質接合型、p-i-n接合型元件之i層等。
本發明之光電轉換元件除具有至少一層本發明之光電轉換層以外,與先前公知之光電轉換元件係同樣地構成。例如,若將圖1(a)示
為一例,則具有支持體1、電極2、電荷轉移層3、光電轉換層4、及電極5依序積層之構造。又,亦可為如圖1(b)所示除去電荷轉移層3之構造,亦可為如圖1(c)所示進而具有電荷轉移層6之構造。
本發明之光電轉換元件中,需要使光自支持體1到達光電轉換層4。為使照射光自支持體1、電極2及電荷轉移層3到達光電轉換層4,較佳為利用透光性之材料形成支持體1、電極2及電荷轉移層3,以透光率成為70%以上之方式設定。
只要支持體1能夠將電極2穩定保持於表面上,則材質或厚度並無限定,但需要具有透明性。因此,支持體之形狀可為板狀亦可為膜狀。透明性係指使光電轉換元件中所使用之特定波長區域、例如可見光區域之光高效率透過之性質。支持體1可使用例如玻璃、透明聚合物膜(聚對苯二甲酸乙二酯(PET)、四乙醯纖維素(TAC)、聚碳酸酯、聚萘二甲酸乙二酯、聚苯硫醚、聚酯碸、間規聚苯乙烯)等。再者,本發明之光電轉換元件較佳為形成於支持體1之表面上,但於電極2本身具有一定程度之硬度,具有獨立性之情形時,亦可設為電極2兼作支持體1之構造,該情形時亦可省略支持體1。
本發明中,將對向配置之一對電極(電極2及電極5)之功函數設為相互相對具有大小關係(即相互之功函數不同)者即可。因此,電極2之功函數相對大於電極5即可。該情形時,較佳為兩電極間之功函數之差為0.5V以上。再者,於各電極與半導體層之間設置有緩衝層,電極上之緩衝層之化合物與電極進行化學鍵結之情形時,有該等制約得到緩和之情況。
作為電極2及電極5,例如可適宜地使用金、鉑、銀等貴金屬類、氧化鋅、氧化銦、氧化錫(NESA)、摻錫氧化銦(ITO)、摻氟氧化錫(FTO)等金屬氧化物、鋰、鋰-銦合金、鈉、鈉-鉀合金、鈣、鎂、鎂-銀合金、鎂-銦合金、銦、釕、鈦、錳、釔、鋁、鋁-鋰合金、鋁-
鈣合金、鋁-鎂合金、鉻、石墨薄膜、此外PEDOT-PSS(Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate),聚(3,4-乙二氧基噻吩)-聚苯乙烯磺酸鹽)等有機導電性化合物等。該等電極物質可單獨使用,或亦可併用複數種。因電極2需要具有透明性,故而使用氧化鋅、NESA、ITO、FTO及PEDOT-PSS等具有透明性之材料。電極2及電極5可使用該等電極物質,與上述光電轉換層4同樣地藉由乾式製程或濕式製程之方法而形成。又,亦可藉由溶膠凝膠法等煅燒而形成。又,電極之厚度亦取決於所使用之電極物質之材料,電極2及電極5一般皆設定為5~1000nm左右,進而較佳為設定為10~500nm左右。
電荷轉移層3及6具有防止電極材料侵入至光電轉換層並反應,或防止於光電轉換層分離之電荷再鍵結而有效率地使電荷向電極2及5移動等作用。作為材料,可列舉PEDOT:PSS、PEO(polyethylene oxide,聚環氧乙烷)、V2O5、氧化鋅、氟化鋰、TiOx、萘四羧酸酐等電荷轉移物質。電荷轉移層3需要具有透明性。於光電轉換層4為P3HT:PCBM之本體異質型之情形時,電荷轉移層3常使用PEDOT:PSS,電荷轉移層6常使用LiF。電荷轉移層3及6可使用該等電荷轉移物質,與上述光電轉換層4同樣地藉由乾式製程或濕式製程之方法而形成。又,電荷轉移層3及6之厚度一般設定為0.01~100nm,進而較佳為設定為0.1~50nm左右。
本發明之光電轉換元件除本發明之有機薄膜太陽電池外,亦可用於光電二極體、光檢測器等。
以下,基於實施例及比較例對本發明進而詳細地進行說明。但本發明不受以下之實施例等之任何限定。
[實施例1]化合物No.11(R1及R6=C12H25、R2、R3、R4及R5=H)之合成
(步驟1)2,9-雙(三異丙基矽基)菲并[1,2-b:8,7-b']二噻吩(7a)之合成
於氬氣氣氛下,向50mL舒倫克管中添加菲并[1,2-b:8,7-b']二噻吩(PDT)(6a)(809mg,2.8mmol,1當量),脫水THF(Tetrahydrofuran,四氫呋喃)(50mL),冷卻至-78℃。其後,滴加正丁基鋰(1.6M於己烷中)(3.85mL,6.2mmol,2.2當量)後,放置冷卻至室溫,並攪拌1小時。攪拌後,冷卻至-78℃,滴加TIPSCI(triisopropylsilyl chloride三異丙基氯矽烷,1.44mL,6.7mmol,2.4當量)後,回流24小時。藉由添加水及1N鹽酸使反應停止,利用氯仿進行萃取。利用飽和氯化鈉水溶液洗淨有機層後,利用無水硫酸鎂進行乾燥,過濾該混合溶液後,使用旋轉蒸發器蒸餾去除溶劑。其後,利用矽膠管柱層析法進行精製,以白色固體之形式以69%(1.17g,1.9mmol)之產率獲得作為目標化合物之7a。將矽膠管柱層析法之條件及化合物7a之分析結果示於以下。
矽膠管柱層析法(Rf=0.38,己烷)。
m.p.:98-100℃
FT-IR(KBr,cm-1):2941(w),2989(m),2864(w),1564(s),1460(m),1284(m),1072(m),949(w),883(m),842(m),686(m),592(m).
1H NMR(600MHz,CDCl3,rt):1.20(d,J=7.2Hz,36H),1.55(sept,J=7.2Hz,6H)7.68(s,2H),8.04(d,J=8.4Hz,2H),8.26(s,2H),8.65(d,J=9Hz,2H).
13C[1H]NMR(150MHz,CDCl3,rt):11.9,18.7,120.2,122.2,123.8,126.8,127.4,133.5,135.8,138.9,142.9.
29Si[1H]NMR(119MHz,CDCl3,rt):2.16.
C36H50S2Si2分析計算值:C,71.70;H,8.36%.實測值:C,71.72;H,8.36%.
(步驟2)4,7-雙(4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷-2-基)-2,9-雙(三異丙基矽基)菲并[1,2-b:8,7-b]二噻吩(8a)之合成
於氬氣氣氛下,向50mL舒倫克管中添加[Ir(OMe)(cod)]2((1,5-環辛二烯)(甲氧基)銥(I)二聚物,50mg,0.075mmol,5mol%)、dtbpy(4,4-di-tert-butyl bipyridine,4,4-二第三丁基聯吡啶,40mg,0.15mmol,10mol%)、B2pin2(雙(頻那醇合)二硼,762mg,3mmol,2當量)、脫水環己烷(30mL),於室溫下攪拌10分鐘。其後,添加7a(905mg,1.5mmol,1當量),於遮光、80℃下攪拌10小時。藉由添加水使反應停止,利用氯仿進行萃取。利用飽和氯化鈉水溶液洗淨有機層後,利用無水硫酸鎂進行乾燥,過濾該混合溶液後,使用旋轉蒸發器蒸餾去除溶劑。其後,利用矽膠管柱層析法進行精製,以白色固體之形式以84%(1.07g,1.26mmol)之產率獲得作為目標化合物之8a。將矽膠管柱層析法之條件及化合物8a之分析結果示於以下。
矽膠管柱層析法(Rf=0.54,己烷/乙酸乙酯=5/1)。
m.p.:174-175℃
FT-IR(KBr,cm-1):2943(w),2891(m),2866(w),1587(m),1463(m),1317(w),1303(w),1143(w),1099(m),974(w),846(m),
680(m),605(s).
1H NMR(600MHz,CDCl3,rt):1.25(d,J=7.8Hz,36H),1.48-1.53(m,30H),8.33(s,2H),8.48(s,2H),9.32(s,2H).
13C[1H]NMR(150MHz,CDCl3,rt):12.0,18.7,25.1,83.9,125.1,126.9,128.6,129.2,135.1,136.1,142.5,142.7.與B相鄰之碳訊號因強度較低故而未觀測到。
11B[1H]NMR(192MHz,CDCl3,rt):31.6.
29Si[1H]NMR(119MHz,CDCl3,rt):1.96.
C48H72B2O4S2Si2分析計算值:C,67.43;H,8.49%.實測值:C,67.14;H,8.52%.
(步驟3)4,7-二溴-2,9-雙(三異丙基矽基)菲并[1,2-b:8,7-b']二噻吩(9a)之合成
向50mL舒倫克管中添加8a(1.07g,1.25mmol,1當量)、CuBr2(1.68g,7.5mmol,6當量)、NMP(N-methyl pyrrolidone,N-甲基吡咯啶酮)/MeOH/H2O(15mL/6mL/3mL),回流15小時。藉由添加1N鹽酸使反應停止,過濾沈澱物後,利用己烷洗淨、乾燥,藉此以白色固體之形式以88%(833mg,1.1mmol)之產率獲得作為目標化合物之9a。將化合物9a之分析結果示於以下。
m.p.:184-185℃
FT-IR(KBr,cm-1):2943(w),2889(m),2864(w),1548(s),1460(m),1087(m),954(w),881(m),648(m),599(m).
1H NMR(600MHz,CDCl3,rt):1.22(d,J=7.2Hz,36H),1.51
(sept,J=7.2Hz,6H)7.79(s,2H),8.09(s,2H),8.66(s,2H).
13C[1H]NMR(150MHz,CDCl3,rt):11.9,18.6,116.8,123.0,123.6,125.9,127.3,133.6,137.3,138.7,143.3.
29Si[1H]NMR(119MHz,CDCl3,rt):2.55.
C36H48Br2S2Si2分析計算值:C,56.83;H,6.36%.實測值:C,56.83;H,6.30%.
(步驟4)4,7-雙十二烷基-2,9-雙(三異丙基矽基)菲并[1,2-b:8,7-b']二噻吩(10a)之合成
於氬氣氣氛下,向50mL舒倫克管中添加1-十二烯(412μL,1.86mmol,3當量)、9-BBN(9-borabicyclo[3.3.1]nonane,9-硼雙環[3.3.1]壬烷)二聚物(232mg,0.95mmol,1.53當量)、脫水THF(12mL),於60℃下攪拌1小時。放置冷卻至室溫後,添加9a(472mg,0.62mmol,1當量)、Pd(dba)2(36mg,0.03mmol,10mol%)、[HPtBu3]BF4(36mg,0.06mmol,20mol%)、氫氧化鉀(209mg,3.72mmol,6當量),回流7小時。藉由添加水使反應停止,利用氯仿進行萃取。利用飽和氯化鈉水溶液洗淨有機層後,利用無水硫酸鎂進行乾燥,過濾該混合溶液後,利用旋轉蒸發器蒸餾去除溶劑。其後,利用矽膠管柱層析法進行精製,以無色液體之形式以87%(506mg,0.54mmol)之產率獲得作為目標化合物之10a。將矽膠管柱層析法之條件及化合物10a之分析結果示於以下。
矽膠管柱層析法(Rf=0.69,己烷)。
FT-IR(KBr,cm-1):2924(w),2854(w),1573(s),1454(w),1382
(s),999(m),883(m),650(m),500(s).
1H NMR(600MHz,CDCl3,rt):0.92(t,J=7.2Hz,6H),1.26(d,J=7.8Hz,36H),1.30-1.37(m,28H),1.45(quin,J=7.8Hz,4H),1.51-1.57(m,10H),1.93(quin,J=7.8Hz,4H),3.22(t,J=7.8Hz,4H),7.77(s,2H),8.17(s,2H),8.42(s,2H).
13C[1H]NMR(150MHz,CDCl3,rt):11.9,14.1,18.7,22.7,29.4,29.6,29.66,29.69,29.73,29.75,29.8,31.1,31.9,35.0,119.1,122.8,125.5,127.5,131.5,134.8,136.2,138.6,143.2.
29Si[1H]NMR(119MHz,CDCl3,rt):2.16.
C60H98S2Si2分析計算值:C,76.69;H,10.51%.實測值:C,76.72;H,10.69%.
(步驟5)4,7-雙十二烷基菲并[1,2-b:8,7-b']二噻吩(3a)之合成
於氬氣氣氛下,向50mL舒倫克管中添加10a(613mg,0.65mmol,1當量)、TBAF(Tetrabutylammonium fluoride,四丁基氟化銨)(1M於THF中)(6.5mL,6.5mmol,10當量)、脫水THF(26mL)、於室溫下攪拌15小時。藉由添加水使反應停止,利用氯仿進行萃取。利用飽和氯化鈉水溶液洗淨有機層後,利用無水硫酸鎂進行乾燥,過濾該混合溶液後,使用旋轉蒸發器蒸餾去除溶劑。其後,利用矽膠管柱層析法進行精製,以白色固體之形式以89%(363mg,0.58mmol)之產率獲得作為目標化合物之3a。將矽膠管柱層析法之條件及化合物3a之分析結果示於以下。
矽膠管柱層析法(Rf=0.52,己烷)
m.p.:84-86℃
FT-IR(KBr,cm-1):3039(m),3072(s),3043(s),2954(w),2914(w),2848(w),1577(s),1469(w),1344(s),1153(m),854(w),802(w),694(w).
1H NMR(600MHz,CDCl3,rt):0.89(t,J=7.8Hz,6H),1.22-1.35(m,28H),1.41(quin,J=7.8Hz,4H),1.51(quin,J=7.8Hz,4H),1.87(quin,J=7.8Hz,4H),3.17(t,J=7.8Hz,4H),7.56(d,J=5.4Hz,2H),7.60(d,J=5.4Hz,2H),8.11(s,2H),8.43(s,2H).
13C[1H]NMR(150MHz,CDCl3,rt):14.1,22.7,29.4,29.6,29.65,29.69,29.71,29.8,31.1,31.9,35.0,119.2,122.6,123.0,125.1,125.7,127.7,136.6,137.3,139.0.
C42H58S2分析計算值:C,80.45;H,9.32%.實測值:C,80.51;H,9.17%.
(步驟6)4,7-雙十二烷基-2,9-雙(三甲基甲錫烷基)菲并[1,2-b:8,7-b']二噻吩(4a)之合成
於氬氣氣氛下,向20ml舒倫克管中添加3a(188mg,0.3mmol,1當量)、脫水THF(12mL),冷卻至0℃。其後,滴加正丁基鋰(1.6M於己烷中)(0.56mL,0.9mmol,3當量)後,回流2小時。攪拌後冷卻至0℃,滴加Me3SnCl(239mg,1.2mmol,4當量)後,於室溫下攪拌12小時。藉由添加水使反應停止,利用二氯甲烷進行萃取。利用飽和氯化鈉水溶液洗淨有機層後,利用無水硫酸鎂進行乾燥,過濾該混合溶液後,使用旋轉蒸發器蒸餾去除溶劑。其後,使用兩次高效液相層
析法進行精製,以淺黃色液體之形式以56%(159mg,0.17mmol)之產率獲得作為目標化合物之4a。將化合物4a之分析結果示於以下。
FT-IR(KBr,cm-1):2924(w),2852(w),1571(s),1465(s),1377(s),950(s),771(m),532(m).
1H NMR(600MHz,CDCl3,rt):0.46(t,J=28.8Hz,18H),0.88(t,J=7.2Hz,6H),1.22-1.36(m,28H),1.43(quin,J=7.8Hz,4H),1.53(quin,J=7.8Hz,4H),1.90(quin,J=7.8Hz,4H),3.20(t,J=7.8Hz,4H),7.65(s,2H),8.15(s,2H),8.40(s,2H).
13C[1H]NMR(150MHz,CDCl3,rt):8.16(t,JC-Sn=177Hz),14.1,22.7,29.4,29.6,29.67,29.69,29.72,29.8,31.0,31.9,35.0,119.1,122.8,125.4,127.2,130.8,136.0,138.6,138.8,143.9.
C48H74S2Sn2分析計算值:C,60.52;H,7.83%.實測值:C,60.74;H,7.96%.
(步驟7)化合物No.11(R1及R6=C12H25,R2、R3、R4及R5=H)之合成
向5mL之小玻璃瓶管中添加4a(62.7mg,0.066mmol,1當量)、BTz-2T-HD(5a,59.7mg,0.066mmol,1當量)、Pd(PPh3)4(1.5mg,1.32μmol,2mol%)後,充入氬氣,塞上塞子密閉。其後,添加脫水甲苯(3.3mL),使用微波照射裝置,於微波照射、180℃下攪拌40分
鐘。其後,添加甲醇/鹽酸(100mL/5mL),於室溫下攪拌3小時。於過濾器中濾取沈澱物,使用索氏萃取器,利用甲醇、己烷、氯仿分別萃取3小時。使用旋轉蒸發器蒸餾去除溶劑,將氯仿成分進行減壓乾燥,藉此以黑紫色固體之形式以77%(69.7mg,0.051mmol)之產率獲得作為目標化合物之化合物No.11。將化合物No.11之分析結果示於以下。
C88H128N2S5分析計算值:C,76.91;H,9.39;N,2.04%.實測值:C,76.54;H,9.26;N,1.99%.
Mw/Mn=31443/21602(測定條件:140℃、o-DCB(Ortho Dichlorobenzene,鄰二氯苯))
[實施例2]化合物No.16(R1及R6=C12H25,R2、R3、R4及R5=H)之合成
首先,利用與實施例1之步驟1~步驟6相同之方法合成化合物4b。向5ml之反應容器中添加4b(56.1mg,0.059mmol)、5b(55.5mg,0.059mmol)及Pd(PPh3)4(1.4mg,1.2μmol)後,充入氬氣,密閉反應容器。其後,將甲苯(2.5mL)添加至反應容器中,利用微波反應裝置於180℃下攪拌40分鐘。將反應混合物冷卻至室溫後,添加至甲醇(100mL)與濃鹽酸(5mL)之混合溶液中,於室溫下攪拌3小時。過濾沈澱物後,按照甲醇、己烷、氯仿、氯苯之順序進行索氏萃取。分別濃縮利用氯仿及氯苯萃取之溶液,使用甲醇進行再沈澱後,於過濾及減壓下進行乾燥,藉此以具有金屬光澤之紫色固體之形式獲得37.9mg(46%)可溶於氯仿之作為目標化合物之化合物No.16。
將化合物No.16之分析結果示於以下。
GPC(o-DCB,140℃):Mn=30.6kDa,PDI=2.05(CHCl3),Mn=42.3kDa,PDI=1.82(PhCl).
[實施例3]化合物No.17(R1及R6=C12H25,R2、R3、R4及R5=H)之合成
首先,利用與實施例1之步驟1~步驟6相同之方法合成化合物4b。向5mL之反應容器中添加4b(60.0mg、0.063mmol)、5c(72.1mg、0.063mmol)及Pd(PPh3)4(1.5mg、1.2μmol)後,充入氬氣,密閉反應容器。其後,將甲苯(2.9mL)添加至反應容器中,利用微波反應裝置於180℃下攪拌40分鐘。將反應混合物冷卻至室溫後,注入至甲醇(100mL)與濃鹽酸(5mL)之混合溶液中,於室溫下攪拌3小時。過濾沈澱物後,按照甲醇、己烷、氯仿之順序進行索氏萃取。分別濃縮利用氯仿萃取之溶液,使用甲醇進行再沈澱後,過濾並於減壓下進行乾燥,藉此以具有金屬光澤之紫色固體之形式獲得90.7mg(89%)之可溶於氯仿之作為目標化合物之化合物No.17。
將化合物No.17之分析結果示於以下。
GPC(o-DCB,140℃):Mn=22.8kDa,PDI=1.39.
[實施例4及5及比較例1]有機薄膜太陽電池元件之製作及評價
使用中性洗劑、離子交換水、丙酮及異丙醇分別對ITO基板(GEOMATEC公司,膜厚:150nm,電阻率:<12Ω/□,透過率:(λ=550nm)≧85%)進行超音波洗淨10分鐘。其後,煮沸放入有基板之
異丙醇10分鐘,乾燥後,進行20分鐘之UV(ultraviolet,紫外線)-臭氧洗淨。於洗淨之基板上通過0.45μm之PVDF(Poly(vinylidene fluoride),聚偏二氟乙烯)製之注射過濾器滴加聚(3,4-乙二氧基噻吩):聚(苯乙烯磺酸鹽)(PEDOT:PSS、CleviousPVPAI4083)之水溶液,以5000rpm旋轉塗佈30秒製成陽極緩衝層。以120℃於加熱板上乾燥10分鐘後,立即搬入至手套箱內。向濃度10g/L之化合物No.16(實施例2中合成)之無水氯苯溶液中以重量比((A)/(B))=1:1~1:2之方式添加可溶性富勒烯衍生物(PC61BM),使其保持於100℃而直接以400rpm旋轉塗佈30秒,繼而以1000rpm旋轉塗佈5秒,藉此於塗佈有(PEDOT:PSS)之基板上製作活性層。於室溫下乾燥後,移至真空蒸鍍裝置,於3×105Pa左右之減壓下通過遮光板真空蒸鍍10nm之鈣作為陰極緩衝層,繼而真空蒸鍍80nm之鋁作為陰極,藉此製作活性區域0.16cm2之塊材異質接合型太陽電池元件,並測定光電轉換效率。光電轉換效率係藉由對於所獲得之塊材異質接合型太陽電池元件自ITO電極側照射大氣質量為1.5G、100mW/cm2之模擬太陽光而測定。
又,作為比較例,除使用化合物A代替化合物No.16以外係利用與實施例4及5相同之方法製作太陽電池元件,並測定光電轉換效率。將該等之結果示於表1。
於將藉由上述實施例所獲得之本發明之苉衍生物用作p型有機半導體之情形時,可確認其顯示較高之光電轉換效率。
Claims (6)
- 一種苉衍生物,其具有至少1個下述通式(1)所表示之結構單元與至少1個選自下述群Y或群Z之結構單元,(式中,A1及A2分別獨立表示單環,R1、R2、R3、R4、R5及R6分別獨立表示氫原子、鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-SiR7R8R9、-NR10R11基、或具有取代基或未經取代之烴基,R1、R2、R3、R4、R5及R6之至少一者不為氫原子,R7、R8、R9、R10或R11分別獨立表示氫原子或具有取代基或未經取代之烴基);(式中,X1及X4表示S、O或NR12,k表示1~4之整數,R12表示經取代或未經取代之烴基,群Y所表示之結構單元中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR13R14基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R13及R14表示經取代或未經取代之烴基);(式中,X2表示S或NR15,X3表示S、NR15、CR16R17或SiR16R17,X5表示S、O或NR15,R15、R16及R17表示經取代或未經取代之烴基,群Z所表示之結構單元中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR18R19基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R18及R19表示經取代或未經取代之烴基)。
- 如請求項1之苉衍生物,其具有至少一個下述通式(2)所表示之結構單元,(式中,A1、A2、R1、R2、R3、R4、R5及R6表示與上述式(1)相同之基,R1、R2、R3、R4、R5及R6之至少一者不為氫原子,Y1及Y2為單鍵或組合1~5個選自下述(Y-1)~(Y-8)之基連結而成之基,Z1表示單鍵或選自下述(Z-1)~(Z-21)之基,n表示1以上且1000以下之整數);(式中,X1及X4表示S、O或NR12,k表示1~4之整數,R12表示經取代或未經取代之烴基,(Y-1)~(Y-4)及(Y-6)~(Y-8)所表示之基中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR13R14基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R13及R14表示經取代或未經取代之烴基); (式中,X2表示S或NR15,X3表示S、NR15、CR16R17或SiR16R17,X5表示S、O或NR15,R15、R16及R17表示經取代或未經取代之烴基,(Z-1)~(Z-21)所表示之基中之氫原子可被取代為鹵素原子、氰基、硝基、羥基、羧基、硫醇基、-NR18R19基、經取代或未經取代之烴基或經取代或未經取代之雜環基,R18及R19表示經取代或未經取代之烴基)。
- 一種光電轉換材料,其係含有作為(A)p型有機半導體材料之如請求項1或2之苉衍生物、及(B)n型有機半導體材料而成。
- 一種光電轉換層,其係將如請求項3之光電轉換材料進行製膜而獲得。
- 一種光電轉換元件,其係具有如請求項4之光電轉換層而成。
- 一種有機薄膜太陽電池,其係具有如請求項5之光電轉換元件而成。
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