JP5911059B2 - 光増感色素ならびに該色素を含む金属酸化物半導体電極および色素増感太陽電池 - Google Patents
光増感色素ならびに該色素を含む金属酸化物半導体電極および色素増感太陽電池 Download PDFInfo
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- JP5911059B2 JP5911059B2 JP2012027274A JP2012027274A JP5911059B2 JP 5911059 B2 JP5911059 B2 JP 5911059B2 JP 2012027274 A JP2012027274 A JP 2012027274A JP 2012027274 A JP2012027274 A JP 2012027274A JP 5911059 B2 JP5911059 B2 JP 5911059B2
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- 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
- C09B47/00—Porphines; Azaporphines
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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
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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
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-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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- 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
- Y02E10/542—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
- Y02E10/549—Organic PV cells
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Description
本発明の光増感色素は、下記式(1)の構造を有する。
本発明は、さらに該光増感色素を用いた金属酸化物半導体電極に関する。本発明の金属酸化物半導体電極は、上述した本発明の光増感色素を金属酸化物半導体の電極の表面に吸着させたものである。この金属酸化物半導体電極は、好ましくは多孔質電極とする。これによって、前記電極の実質的な表面積を増大させることができ、前記電極への光増感色素の吸着量を増大させて、前記金属酸化物半導体電極を含む太陽電池の光電変換効率を増大させることができるようになる。
本発明はさらに、透明電極1、上記金属酸化物半導体電極2、電解質3、および対電極4を含む色素増感太陽電池に関する(図1参照)。
2‐ホルミル‐5‐ヘキシルチオフェンの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)0.98(t,9H),1.45(m,12H),1.61(quin,6H),1.96(quin,6H),3.14(t,6H),7.17(d,3H),7.71(d,3H),8.35(d,2H),8.53(d,2H),8.89(d,2H),9.23(d,2H),9.24(s,4H)
2‐(4‐ヘキシルフェニル)‐4,4,5,5‐テトラメチル‐1,3,2‐ジオキサボロランの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)0.92(t,9H),1.30‐1.42(m,18H),1.69(quin,6H),2.69(t,6H),7.31(d,6H),7.67(d,3H),7.79(d,6H),7.87(d,3H),8.36(d,2H),8.52(d,2H),8.91‐9.34(m,8H)
9‐(2‐チオフェン)‐3,6‐ジ‐t‐ブチルカルバゾールの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)1.53(s,54H),7.63(dd,3H),7.67(t,6H),7.88(t,6H),8.01(dd,3H),8.22(s,6H),8.41(d,2H),8.59(d,2H),9.02(d,2H),9.42(d,2H),9.48(s,4H)
5‐ホルミルチオフェン‐2‐カルボン酸メチルエステルの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)0.98(t,9H),1.41‐1.47(m,12H),1.60(quin,6H),1.96(quin,6H),3.14(t,6H),7.17(d,3H),7.70(d,3H),7.94(d,2H),8.26(d,2H),9.12(d,2H),9.23(s,4H),9.26(d,2H)
5,10,15‐トリ(5‐メチルチオフェン‐2‐イル)‐20‐(4‐メトキシカルボニルフェニル)ポルフィリンの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)2.83(s,9H),7.17(d,3H),7.68(d,3H),8.35(d,2H),8.52(d,2H),8.88‐9.26(m,8H)
5‐ブロモ‐5'‐ホルミル‐2,2'‐ビチオフェンの合成
1H‐NMR(δH/ppm,THF,400MHz)0.92(t,9H),1.30‐1.40(m,18H),1.67(quin,6H),2.65(t,6H),7.25(d,6H),7.41(t,3H),7.45(t,3H),7.64(d,6H),7.70(t,3H),7.86(t,3H),8.31(d,2H),8.45(d,2H),8.86(d,2H),9.25(d,2H),9.27(s,4H)
比較例として、以下の化合物を合成した。
5,10,15‐トリ(5‐ヘキシルチオフェン‐2‐イル)‐20‐(4‐メトキシカルボニルフェニル)ポルフィリンの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)0.98(t,9H),1.40‐1.50(m,12H),1.60(quin,6H),1.96(quin,6H),3.14(t,6H),7.17(d,3H),7.71(d,3H),8.35(d,2H),8.54(d,2H),8.78‐9.14(m,8H)
5,10,15‐トリ(5‐ヘキシルチオフェン‐2‐イル)‐20‐(4‐メトキシカルボニルフェニル)ポルフィリン銅(II)錯体の合成
5,10,15‐トリ(5‐ヘキシルチオフェン‐2‐イル)‐20‐(4‐メトキシカルボニルフェニル)ポルフィリンコバルト(II)錯体の合成
5,10,15‐トリ(5‐ヘキシルチオフェン‐2‐イル)‐20‐(4‐(4'‐メトキシカルボニル)ビフェニル)ポルフィリンの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)0.96‐1.00(m,9H),1.44‐1.46(m,12H),1.60(quin,6H),1.96(quin,6H),3.14(t,6H),7.17(d,3H),7.70(d,3H),8.04(d,4H),8.33(d,4H),8.98‐9.25(m,8H)
5,10,15‐トリメシチル‐20‐(4‐メトキシカルボニルフェニル)ポルフィリンの合成
1H‐NMR(δH/ppm,CDCl3,400MHz)1.85(s,18H),2.64(s,9H),7.29(s,6H),8.37(s,2H),8.51(s,2H),8.78‐8.83(m,8H)
(1)以下の手順により、上記合成例により調製した各種色素A〜Fおよび比較例1〜5を用いた色素増感太陽電池を作製した。
上記のようにして得られた色素増感太陽電池につきその性能を評価した。
光電変換効率(%)=
100×[(短絡電流密度×開放電圧×曲線因子)/(照射太陽光エネルギー)
2 金属酸化物半導体電極
3 電解質
4 対電極
Claims (6)
- 下記式(1)を有する太陽電池用光増感色素。
- 前記Aは、分岐を含んでもよいC1〜20のアルキル、C1〜20のアルコキシ、ハロゲンからなる群から選択される置換基で置換されたアリールまたはヘテロアリールであることを特徴とする請求項1に記載の光増感色素。
- 前記Bは、チオフェン環、ピロール環、フラン環、イミダゾール環、ピラゾール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、1,2,3−トリアジン環、キノリン環、イソキノリン環、キナゾリン環、フタラジン環、プテリジン環、クマリン環、クロモン環、1,4−ベンゾジアゼピン環、インドール環、ベンズイミダゾール環、ベンゾフラン環、プリン環、アクリジン環、フェノキサジン環、フェノチアジン環からなる群から選択される無置換または置換基を有するヘテロアリールであることを特徴とする請求項1または2に記載の光増感色素。
- 前記Bは、分岐を含んでもよいC1〜20のアルキル、C1〜20のシクロアルキル、アリール、ヘテロアリール、アルキルアリール、アルキルヘテロアリール、アリールアリール、アリールヘテロアリール、ヘテロアリールアリール、ヘテロアリールヘテロアリール、アルキルアリールアリール、アルキルアリールヘテロアリール、アルキルヘテロアリールアリール、アルキルヘテロアリールヘテロアリール、C1〜20のアルコキシ、およびハロゲンからなる群から選択される置換基により置換されたヘテロアリールであることを特徴とする請求項1〜3のいずれか一項に記載の光増感色素。
- 請求項1〜4のいずれか一項に記載の光増感色素を酸化物半導体上に吸着させたことを特徴とする酸化物半導体電極。
- 請求項5の酸化物半導体電極、透明電極、電解質および対電極を含む色素増感太陽電池。
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