JP2007084792A - 有機色素組成物及び光電池への使用 - Google Patents
有機色素組成物及び光電池への使用 Download PDFInfo
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- ZKZBPNGNEQAJSX-UHFFFAOYSA-N selenocysteine Natural products [SeH]CC(N)C(O)=O ZKZBPNGNEQAJSX-UHFFFAOYSA-N 0.000 description 1
- 235000016491 selenocysteine Nutrition 0.000 description 1
- 229940055619 selenocysteine Drugs 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/652—Cyanine dyes
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y02E10/542—Dye sensitized solar cells
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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
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Abstract
【解決手段】1種以上のクロコニン誘導体を含有する組成物を提供する。この組成物を半導体層上に配置し、さらに半導体層を導電性表面上に配置して色素増感電極を構成することができる。色素増感電極を対電極及びレドックス電解質と合わせて、光電池を組み立てることができる。光電池は単一セルで使用しても、他のセルとタンデムで使用してもよい。
【選択図】なし
Description
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、ブチル基、メトキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iは構造式IIのクロコニン誘導体を含まないことも条件とする。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、ブチル基、メトキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iが次の構造式IIのクロコニン誘導体を含まないことも条件とする。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、C1−C5アルキル基、C1−C5アルコキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに構造式Iは以下の構造式IIのクロコニン誘導体を含まないことも条件とする。
クロコン酸の合成
5gのロジゾン酸ナトリウムを250mLの水に溶解した溶液に、21gの炭酸カリウム及び14gの二酸化マグネシウムを添加した。混合物を攪拌しながら1時間還流した後、直ちに濾過した。得られた濾液をHCl水溶液で酸性にし、pH6〜7とし、次いで塩化バリウム(BaCl2)の水溶液を添加した。沈殿を回収し、真空下で乾燥し、7.42gの金色のクロコン酸バリウムを得た。
13C−NMR(D2O)δ: 191.7,181.2,160.6,149.0
実施例2
2,3,3−トリメチル−5−カルボキシル−インドレニンの合成
0.1モルの4−カルボキシフェニルヒドラジン及び8.6g(10.7mL、0.1モル)のイソプロピルメチルケトンを一緒に70℃に4時間加熱した。室温まで冷却した後、11mL(0.1モル)の60%H2SO4を添加し、混合物を90℃に3時間加熱し、その後室温にて重炭酸ナトリウムで中和した。有機層をエチルエーテルで抽出し、硫酸ナトリウム(Na2SO4)で乾燥した。溶剤の除去後、残留物をシリカゲルでのフラッシュクロマトグラフィーで精製し、2,3,3−トリメチル−5−カルボキシル−インドレニンを収率59%で得た。
1H NMR(400MHz,CDCl3): δ8.16(d,J=8.19Hz,1H),8.07(s,1H),7.65(d,J=8.18Hz,1H),2.38(s,3H),1.38(s,6H)
実施例3
構造式VIIIのクロコニン誘導体の合成
実施例2で合成した2,3,3−トリメチル−5−カルボキシル−インドレニン(4ミリモル)及び実施例1で合成したクロコン酸(290mg、2ミリモル)をn−ブタノール/トルエン(1:1v/v)の混合溶剤(20mL)に溶解し、110℃に加熱した。ディーンスタークトラップを用いて、水を共沸除去した。TLCにより反応をモニターした。反応終了後、得られた溶液を蒸発させて粗生成物を得た。クロコニン誘導体粗生成物をシリカゲルでのフラッシュクロマトグラフィー、次いでメタノールからの再結晶によって精製し、クロコニン誘導体VIIIを得た。収率67%。
1H NMR(400MHz,d−DMSO) δ: 8.12(s,2H),7.99(d,J=8.09Hz,2H),7.65−7.55(m,2H),6.06(s,2H),1.54(s,12H)
FTIR(KBr,cm−1): 1713(s),1682(m),1626(w),1534(s),1495(s),1343(s),1313(s),1182(s),961(m)
実施例4
1−カルボキシエチル−2,3,3−トリメチル−4,5−ベンゾインドレニニウムブロミドの合成
5.81g(27.8ミリモル)の2,3,3−トリメチル−4,5−ベンゾインドレニン及び4.23g(27.7ミリモル)の3−ブロモピロピオン酸を80mLの1,2−ジクロロベンゼンに溶解した。混合物を100℃で20時間攪拌して、針状結晶を得た。生成物を濾過によって回収し、固形物をエーテルで洗浄し、真空下乾燥して、9.0g(90%)の1−カルボキシエチル−2,3,3−トリメチル−4,5−ベンゾインドレニニウムブロミドを得た。
1H NMR(DMSO,400 MHz): δ 8.38(d,J=8.3Hz,1H),8.29(d,J=8.9Hz,1H),8.22(d,J=8.0Hz,1H),8.18(d,J=8.9Hz,1H),7.79(t,J=7.0Hz,1H),7.73(t,J=7.0Hz,1H),4.78(t,J=6.9Hz,2H),3.05(t,J=6.9Hz,2H),2.97(s,3H),1.76(s,6H)
FTIR(KBr,cm−1) 1591(m),1513(m),1478(m),1426(s),1360(m),1313(w),1139(m),1095(s),1008(m),930(m),665(m)
実施例5
構造式XIIのクロコニン誘導体の合成
実施例4で合成した1−カルボキシエチル−2,3,3−トリメチル−4,5−ベンゾインドレニニウムブロミド(4ミリモル)、実施例1で合成したクロコン酸(290mg、2ミリモル)及びピリジン(2ミリモル)をn−ブタノール/トルエン(1:1v/v)の混合溶剤(20mL)に溶解した。得られた混合液を110℃に加熱し、生成した水をディーンスタークトラップを用いて、共沸除去した。TLCにより反応をモニターした。反応終了後、得られた溶液を蒸発させて粗生成物を得た。クロコニン誘導体粗生成物をブタノールでエステル化し、シリカゲルでのフラッシュクロマトグラフィー、次いでメタノールからの再結晶によって精製し、クロコニン誘導体XIIを得た。
1H NMR(400MHz,CDCl3): δ 8.11(d,J=8.3Hz,2H),7.97−7.90(m,4H),7.61(t,J=7.3Hz,2H),7.54−7.44(m,4H),6.40(s,2H),4.68(t,J=6.8Hz,4H),3.97(t,J=6.7Hz,4H),2.80(t,J=6.8Hz,4H),1.90(s,12H),1.53−1.42(m,4H),1.34−1.18(m,4H),0.82(t,J=7.3Hz,6H)
FTIR(KBr,cm−1): 1739(m),1565(m),1495(s),1452(s),1334(s),1313(m),1265(m),1026(m),952(m)
ESI−MS: C49H52N2O7(100%)の実測値781.335; C49H52N2O7 の計算値780.910
実施例6
公知色素N3(比較例1)に対するクロコニン誘導体VIII及びXIIのUV特性の測定
クロコニン誘導体VIII及びXIIで例示される本発明のクロコニン色素を、色素増感太陽電池への使用に適当か否か評価した。クロコニン誘導体VIII及びXIIの光吸収特性を比較例1の公知の色素N3(N3=Ru(bpy(COOH)2)2(NCS)2、Solaronix社製)と比較した。VIII、XII及びN3それぞれのUV−可視スペクトルを紫外可視近赤外分光光度計UV−3150(島津製作所)で測定した。データを表1にまとめる。データから、本発明のクロコニン誘導体の最大吸収が790nm付近に観察されることが分かる。その分子吸収係数は104程度であり、公知の色素N3に観察される値のほぼ5倍であった。
クロコニン誘導体VIIIの光電池性能
クロコニン誘導体VIIIを色素増感太陽電池で試験した。すなわち、ナノ結晶性TiO2層を50℃で、VIIIのDMSO/DMF混合物への濃縮液(DMSO/DMF混合物(DMSO約12容量%)中に約2mM)の少量(25〜50μL)で処理した。15〜20分の処理後、TiO2層をDMF及びエタノールでリンスした。10μmのTiO2フィルムから通常の方法で色素増感太陽電池(セル)を作製した。普通の電解液(0.5M Pr4NI,0.1M LiI,0.45M tBuPyr,0.05 M I2)を使用して試験セルを組み立て、これらを1太陽照射条件で試験した。
Claims (10)
- 次の構造式Iの1種以上のクロコニン誘導体を含有する組成物。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、ブチル基、メトキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iは次の構造式IIのクロコニン誘導体を含まないことも条件とする。
- クロコニン誘導体が次の構造式VIIで表される、請求項1記載の組成物。
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であるが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)である場合には、R1は水素原子、ブチル基、メトキシ基、ニトロ基又はアセトアミド基ではないことを条件とする。 - クロコニン誘導体が次の構造式XIで表される、請求項1記載の組成物。
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であるが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)である場合には、R3及びR4は水素原子ではないことを条件とする。 - 次の構造式Iの1種以上のクロコニン誘導体を含有する組成物。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、C1−C5アルキル基、C1−C5アルコキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iは次の構造式IIのクロコニン誘導体を含まないことも条件とする。
- (a)導電性表面を有する基板、
(b)前記導電性表面上に配置された電子輸送層、及び
(c)前記導電性表面上に配置された1種以上のクロコニン誘導体を含有する組成物
を備える色素増感電極。 - 前記組成物が次の構造式Iの1種以上のクロコニン誘導体を含有する、請求項5記載の色素増感電極。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、ブチルC1−C5アルキル基、C1−C5アルコキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iは次の構造式IIのクロコニン誘導体を含まないことも条件とする。
- (a)導電性表面を有する基板、前記導電性表面上に配置された電子輸送層、及び前記電子輸送層上に配置された1種以上のクロコニン誘導体を含有する組成物を含む色素増感電極、
(c)対電極、及び
(d)前記色素増感電極及び対電極に接触した正孔輸送層
を備える光電池。 - 前記組成物が次の構造式Iの1種以上のクロコニン誘導体を含有する、請求項7記載の光電池。
a及びbは各々独立に0〜4の整数であり、
R3及びR4は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基、C3−C30芳香族基、−(CH2)nCOOA基又は−(CH2)nSO3A基であり、nは1〜50の整数で、Aは水素原子、金属カチオン、ペプチド基又は炭水化物基であり、
X及びYは各々独立に、酸素原子、硫黄原子、セレン原子、N−R5基又はC−R6R7基であり、R5、R6及びR7は各々独立に、水素原子、C1−C30脂肪族基、C3−C30脂環式基又はC3−C30芳香族基であり、
さらに、R1と隣接R2基が互いに環構造を形成してもよいし、及び/又は2つの隣接R2基が互いに環構造を形成してもよいが、
ただし、X及びYがともにイソプロピリデン(C(CH3)2)であり、a及びbがともに0であり、R3及びR4がともに水素原子である場合には、R1は水素原子、ブチルC1−C5アルキル基、C1−C5アルコキシ基、ニトロ基又はアセトアミド基ではないことを条件とし、さらに、構造式Iは次の構造式IIのクロコニン誘導体を含まないことも条件とする。
- 前記光電池が単一セルとして又は他の光電池とタンデムで光起電力型電源である、請求項7記載の光電池。
- 複数の前記光電池がタンデムに配列されて光起電力型電源として作用する、請求項7記載の光電池。
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Also Published As
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AU2006203352A1 (en) | 2007-02-22 |
US20070028961A1 (en) | 2007-02-08 |
EP1752497A3 (en) | 2008-02-27 |
CN1908072A (zh) | 2007-02-07 |
EP1752497A2 (en) | 2007-02-14 |
MXPA06008823A (es) | 2007-02-16 |
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