JP5784443B2 - 光電変換素子及び光電気化学電池、並びにこれに用いられる金属錯体色素 - Google Patents
光電変換素子及び光電気化学電池、並びにこれに用いられる金属錯体色素 Download PDFInfo
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- JP5784443B2 JP5784443B2 JP2011214662A JP2011214662A JP5784443B2 JP 5784443 B2 JP5784443 B2 JP 5784443B2 JP 2011214662 A JP2011214662 A JP 2011214662A JP 2011214662 A JP2011214662 A JP 2011214662A JP 5784443 B2 JP5784443 B2 JP 5784443B2
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- 238000006243 chemical reaction Methods 0.000 title claims description 76
- 239000000434 metal complex dye Substances 0.000 title claims description 24
- 239000000975 dye Substances 0.000 claims description 145
- -1 phosphoryl group Chemical group 0.000 claims description 73
- 239000004065 semiconductor Substances 0.000 claims description 71
- 239000003446 ligand Substances 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 239000010419 fine particle Substances 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 150000002500 ions Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 21
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- 238000010521 absorption reaction Methods 0.000 claims description 18
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- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000005619 boric acid group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000005499 phosphonyl group Chemical group 0.000 claims description 14
- 108091008695 photoreceptors Proteins 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
- YXBZNMSPFZDRFZ-UHFFFAOYSA-M methanol;tetrabutylazanium;hydroxide Chemical compound [OH-].OC.CCCC[N+](CCCC)(CCCC)CCCC YXBZNMSPFZDRFZ-UHFFFAOYSA-M 0.000 claims description 12
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 6
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- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
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- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 4
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical group O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 4
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
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- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 3
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
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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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
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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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/141—Bis styryl dyes containing two radicals C6H5-CH=CH-
-
- 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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JP2011214662A JP5784443B2 (ja) | 2011-09-29 | 2011-09-29 | 光電変換素子及び光電気化学電池、並びにこれに用いられる金属錯体色素 |
PCT/JP2012/074275 WO2013047384A1 (ja) | 2011-09-29 | 2012-09-21 | 光電変換素子及び光電気化学電池、並びにこれに用いられる金属錯体色素 |
KR1020147011304A KR101890008B1 (ko) | 2011-09-29 | 2012-09-21 | 광전 변환 소자 및 광전기 화학 전지, 그리고 이것에 사용되는 금속 착물 색소 |
CN201280047437.XA CN103843093B (zh) | 2011-09-29 | 2012-09-21 | 光电转换元件及光电化学电池、以及其中所用的金属络合物色素 |
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JP6017491B2 (ja) * | 2013-04-12 | 2016-11-02 | 富士フイルム株式会社 | 光電変換素子、色素増感太陽電池、金属錯体色素、色素溶液、色素吸着電極および色素増感太陽電池の製造方法 |
WO2017047410A1 (ja) | 2015-09-17 | 2017-03-23 | 富士フイルム株式会社 | 光電変換素子、色素増感太陽電池、色素組成物および酸化物半導体電極 |
EP3439002A4 (en) * | 2016-03-30 | 2019-04-10 | Fujifilm Corporation | COLORING SOLUTION FOR PHOTOELECTRIC CONVERSION ELEMENT, COLORING SOLUTION PREPARATION, AND METHOD FOR MANUFACTURING PHOTOELECTRIC CONVERSION ELEMENT |
KR20190055138A (ko) | 2016-09-29 | 2019-05-22 | 후지필름 가부시키가이샤 | 광전 변환 소자, 색소 증감 태양 전지, 금속 착체 색소, 색소 용액 및 산화물 반도체 전극 |
JP2020127007A (ja) * | 2019-02-01 | 2020-08-20 | 株式会社リコー | 光電変換素子、太陽電池モジュール、電源モジュール、及び電子機器 |
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TWI379836B (en) | 2009-04-10 | 2012-12-21 | Nat Univ Tsing Hua | Panceromatic photosensitizers and dye-sensitized solar cell using the same |
JP5776099B2 (ja) | 2009-08-13 | 2015-09-09 | 島根県 | 遷移金属錯体、光増感色素及び該色素を含む酸化物半導体電極及び色素増感太陽電池 |
JP2012084250A (ja) * | 2010-10-07 | 2012-04-26 | Konica Minolta Business Technologies Inc | 光電変換素子及び太陽電池 |
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