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WO2009020098A1 - Sensitizing dye for dye-sensitized solar cell having extended π-electron conjugated system - Google Patents

Sensitizing dye for dye-sensitized solar cell having extended π-electron conjugated system Download PDF

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Publication number
WO2009020098A1
WO2009020098A1 PCT/JP2008/063968 JP2008063968W WO2009020098A1 WO 2009020098 A1 WO2009020098 A1 WO 2009020098A1 JP 2008063968 W JP2008063968 W JP 2008063968W WO 2009020098 A1 WO2009020098 A1 WO 2009020098A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
formula
optionally substituted
hydrogen atom
aliphatic hydrocarbon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2008/063968
Other languages
French (fr)
Japanese (ja)
Inventor
Shozo Yanagida
Kazuharu Suzuki
Ke-Jian Jiang
Teruhisa Inoue
Koichiro Shigaki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
University of Osaka NUC
Original Assignee
Nippon Kayaku Co Ltd
Osaka University NUC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd, Osaka University NUC filed Critical Nippon Kayaku Co Ltd
Priority to JP2009526451A priority Critical patent/JP5466943B2/en
Publication of WO2009020098A1 publication Critical patent/WO2009020098A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • 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
    • 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
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Hybrid Cells (AREA)

Abstract

Disclosed is a low-cost photoelectric converter having high conversion efficiency, which uses dye-sensitized semiconductor fine particles. Also disclosed is a solar cell using such a photoelectric converter. Specifically disclosed is a photoelectric converter wherein a thin film of oxide semiconductor fine particles, which is formed on a substrate, is loaded with a metal complex dye represented by the formula (1) below or a salt thereof. (In the formula (1), rings a, b, c and d may respectively have 1-3 substituents; m represents an integer of 1 or 2; and Z is represented by the following formula (2) or (3).) (In the formula (2), A1 and A2 each represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon residue or an alkoxyl group; and A3 represents a hydrogen atom or an optionally substituted aliphatic hydrocarbon residue. In the formula (3), A4 and A5 each represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon residue or an alkoxyl group; and A6 represents a hydrogen atom or an optionally substituted aliphatic hydrocarbon residue.)
PCT/JP2008/063968 2007-08-08 2008-08-04 Sensitizing dye for dye-sensitized solar cell having extended π-electron conjugated system Ceased WO2009020098A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009526451A JP5466943B2 (en) 2007-08-08 2008-08-04 Sensitizing dye for dye-sensitized solar cell with expanded pi-electron conjugate system

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007207286 2007-08-08
JP2007-207286 2007-08-08

Publications (1)

Publication Number Publication Date
WO2009020098A1 true WO2009020098A1 (en) 2009-02-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/063968 Ceased WO2009020098A1 (en) 2007-08-08 2008-08-04 Sensitizing dye for dye-sensitized solar cell having extended π-electron conjugated system

Country Status (2)

Country Link
JP (1) JP5466943B2 (en)
WO (1) WO2009020098A1 (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009215539A (en) * 2008-02-19 2009-09-24 National Central Univ Photosensitizer dye
WO2009133806A1 (en) * 2008-05-02 2009-11-05 ペクセル・テクノロジーズ株式会社 Dye-sensitized photoelectric conversion element
WO2010021378A1 (en) * 2008-08-22 2010-02-25 日本化薬株式会社 Dye-sensitized photovoltaic device
WO2009107100A3 (en) * 2008-02-27 2010-04-22 Ecole Polytechnique Federale De Lausanne (Epfl) High molecular extinction coefficient metal dyes
JP2011037788A (en) * 2009-08-13 2011-02-24 Shimane Prefecture Transition metal complex, photosensitizer dye, and oxide semiconductor electrode and dye-sensitized solar cell containing the dye
GB2474956A (en) * 2009-10-30 2011-05-04 Everlight Usa Inc Electrolyte composition
JP2011157449A (en) * 2010-01-29 2011-08-18 Shimane Prefecture Transition metal complex and compound useful as ligand thereof, as well as oxide semiconductor electrode containing the same and dye-sensitized solar cell
WO2011118581A1 (en) * 2010-03-24 2011-09-29 富士フイルム株式会社 Method for manufacturing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
WO2011118715A1 (en) * 2010-03-26 2011-09-29 日産化学工業株式会社 Dye for dye-sensitized solar cell, and dye-sensitized solar cell
WO2011118580A1 (en) * 2010-03-24 2011-09-29 富士フイルム株式会社 Photoelectric conversion element and photoelectrochemical cell
WO2011145551A1 (en) 2010-05-17 2011-11-24 日本化薬株式会社 Photoelectric conversion element using thermosetting sealing agent for photoelectric conversion element
JP2011243379A (en) * 2010-05-17 2011-12-01 Fujifilm Corp Photoelectric conversion element, photoelectrochemical cell and dye solution for photoelectric conversion element
JP2012053984A (en) * 2010-08-03 2012-03-15 Fujifilm Corp Photoelectric converter, photoelectrochemical cell, and manufacturing methods of photoelectric converter and photoelectrochemical cell
JP2012053985A (en) * 2010-08-03 2012-03-15 Fujifilm Corp Photoelectric conversion element, and photoelectrochemical battery using the same
US8143399B2 (en) 2008-02-19 2012-03-27 National Central University Photosensitizer dye
JP2012508227A (en) * 2008-11-11 2012-04-05 エコール ポリテクニーク フェデラル ドゥ ローザンヌ（エーペーエフエル） A novel anchoring ligand for sensitizers in dye-sensitized photovoltaic devices
EP2372734A3 (en) * 2010-04-05 2012-12-26 Samsung SDI Co., Ltd. Ruthenium complex and dye-sensitized fuel cell using the same
EP2578644A4 (en) * 2010-06-02 2013-11-13 Fujifilm Corp METAL COMPLEX DYE, PHOTOELECTRIC CONVERSION ELEMENT, AND SOLAR COLOR CELL
WO2014084296A1 (en) 2012-11-30 2014-06-05 日本化薬株式会社 Dye-sensitized solar cell
CN109273602A (en) * 2018-09-10 2019-01-25 天津师范大学 Application of 2,2'-bipyridyl ligand metal organic hybrid materials in the field of optoelectronics

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000106223A (en) * 1998-09-29 2000-04-11 Fuji Photo Film Co Ltd Photoelectric conversion element
JP2001291534A (en) * 2000-01-31 2001-10-19 Fuji Photo Film Co Ltd Photoelectric conversion element and photocell and metal complex pigment
JP2004296170A (en) * 2003-03-26 2004-10-21 Mitsui Chemicals Inc Material for photoelectric transfer element, photoelectric transfer element, and ruthenium complex compound
JP2005135656A (en) * 2003-10-28 2005-05-26 Shozo Yanagida Photoelectric conversion element
JP2007112987A (en) * 2005-09-22 2007-05-10 Sumitomo Chemical Co Ltd Compound, photoelectric conversion element and photoelectrochemical cell
WO2007072970A1 (en) * 2005-12-21 2007-06-28 Sumitomo Chemical Company, Limited Compound, photoelectric converter and photoelectrochemical cell
WO2007091525A1 (en) * 2006-02-08 2007-08-16 Shimane Prefectural Government Photosensitizer dye

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000106223A (en) * 1998-09-29 2000-04-11 Fuji Photo Film Co Ltd Photoelectric conversion element
JP2001291534A (en) * 2000-01-31 2001-10-19 Fuji Photo Film Co Ltd Photoelectric conversion element and photocell and metal complex pigment
JP2004296170A (en) * 2003-03-26 2004-10-21 Mitsui Chemicals Inc Material for photoelectric transfer element, photoelectric transfer element, and ruthenium complex compound
JP2005135656A (en) * 2003-10-28 2005-05-26 Shozo Yanagida Photoelectric conversion element
JP2007112987A (en) * 2005-09-22 2007-05-10 Sumitomo Chemical Co Ltd Compound, photoelectric conversion element and photoelectrochemical cell
WO2007072970A1 (en) * 2005-12-21 2007-06-28 Sumitomo Chemical Company, Limited Compound, photoelectric converter and photoelectrochemical cell
WO2007091525A1 (en) * 2006-02-08 2007-08-16 Shimane Prefectural Government Photosensitizer dye

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEN C.-Y. ET AL., ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 45, no. 35, 4 September 2006 (2006-09-04), pages 5822 - 5825 *
JIANG K.-J. ET AL.: "A novel ruthenium sensitizer with a hydrophobic 2-thiophen-2-yl-vinyl-conjugated bipyridyl ligand for effective dye sensitized TiO2 solar cells", CHEMICAL COMMUNICATIONS, no. 23, 21 June 2006 (2006-06-21), pages 2460 - 2462 *
MOZER A.J. ET AL.: "Efficient dye-sensitized solar cells based on a 2'-thiophen-2-yl-vinyl-conjugated ruthenium photosensitizer and a conjugated polymer hole conductor", APPLIED PHYSICS LETTERS, vol. 89, no. 4, 24 June 2006 (2006-06-24), pages 043509-1 - 043509-3, XP012088191 *

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8143399B2 (en) 2008-02-19 2012-03-27 National Central University Photosensitizer dye
JP2009215539A (en) * 2008-02-19 2009-09-24 National Central Univ Photosensitizer dye
AU2009200356B2 (en) * 2008-02-19 2011-03-10 National Central University Photosensitizer Dye
JP2011513530A (en) * 2008-02-27 2011-04-28 エコール ポリテクニーク フェデラル ドゥ ローザンヌ（エーペーエフエル） Polymer extinction coefficient metal dye
US9716240B2 (en) 2008-02-27 2017-07-25 Ecole Polytechnique Federale De Lausanne (Epfl) High molecular extinction coefficient metal dyes
WO2009107100A3 (en) * 2008-02-27 2010-04-22 Ecole Polytechnique Federale De Lausanne (Epfl) High molecular extinction coefficient metal dyes
JP5479327B2 (en) * 2008-05-02 2014-04-23 ペクセル・テクノロジーズ株式会社 Dye-sensitized photoelectric conversion element
WO2009133806A1 (en) * 2008-05-02 2009-11-05 ペクセル・テクノロジーズ株式会社 Dye-sensitized photoelectric conversion element
WO2010021378A1 (en) * 2008-08-22 2010-02-25 日本化薬株式会社 Dye-sensitized photovoltaic device
KR101561324B1 (en) 2008-08-22 2015-10-16 니폰 가야꾸 가부시끼가이샤 Dye-sensitized photovoltaic device
AU2009283460B2 (en) * 2008-08-22 2014-12-04 Nippon Kayaku Kabushiki Kaisha Dye-sensitized photovoltaic device
US8513520B2 (en) 2008-08-22 2013-08-20 Nippon Kayaku Kabushiki Kaisha Dye-sensitized photovoltaic device comprising a ruthenium metal complex
JP2012508227A (en) * 2008-11-11 2012-04-05 エコール ポリテクニーク フェデラル ドゥ ローザンヌ（エーペーエフエル） A novel anchoring ligand for sensitizers in dye-sensitized photovoltaic devices
JP2011037788A (en) * 2009-08-13 2011-02-24 Shimane Prefecture Transition metal complex, photosensitizer dye, and oxide semiconductor electrode and dye-sensitized solar cell containing the dye
GB2474956A (en) * 2009-10-30 2011-05-04 Everlight Usa Inc Electrolyte composition
AU2010237860B2 (en) * 2009-10-30 2011-12-01 Everlight Usa, Inc. Electrolyte composition and dye-sensitized solar cell using the same
JP2011157449A (en) * 2010-01-29 2011-08-18 Shimane Prefecture Transition metal complex and compound useful as ligand thereof, as well as oxide semiconductor electrode containing the same and dye-sensitized solar cell
WO2011118580A1 (en) * 2010-03-24 2011-09-29 富士フイルム株式会社 Photoelectric conversion element and photoelectrochemical cell
WO2011118581A1 (en) * 2010-03-24 2011-09-29 富士フイルム株式会社 Method for manufacturing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
CN102792516A (en) * 2010-03-24 2012-11-21 富士胶片株式会社 Method for preparing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
US20120305905A1 (en) * 2010-03-24 2012-12-06 Fujifilm Corporation Method of producing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
US9419318B2 (en) 2010-03-24 2016-08-16 Fujifilm Corporation Method of producing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
CN102792516B (en) * 2010-03-24 2015-11-18 富士胶片株式会社 Method for preparing photoelectric conversion element, photoelectric conversion element and photoelectrochemical cell
WO2011118715A1 (en) * 2010-03-26 2011-09-29 日産化学工業株式会社 Dye for dye-sensitized solar cell, and dye-sensitized solar cell
JP5713005B2 (en) * 2010-03-26 2015-05-07 浩司 瀬川 Dye for dye-sensitized solar cell and dye-sensitized solar cell
EP2372734A3 (en) * 2010-04-05 2012-12-26 Samsung SDI Co., Ltd. Ruthenium complex and dye-sensitized fuel cell using the same
WO2011145551A1 (en) 2010-05-17 2011-11-24 日本化薬株式会社 Photoelectric conversion element using thermosetting sealing agent for photoelectric conversion element
JP2011243379A (en) * 2010-05-17 2011-12-01 Fujifilm Corp Photoelectric conversion element, photoelectrochemical cell and dye solution for photoelectric conversion element
EP2578644A4 (en) * 2010-06-02 2013-11-13 Fujifilm Corp METAL COMPLEX DYE, PHOTOELECTRIC CONVERSION ELEMENT, AND SOLAR COLOR CELL
JP2012053985A (en) * 2010-08-03 2012-03-15 Fujifilm Corp Photoelectric conversion element, and photoelectrochemical battery using the same
JP2012053984A (en) * 2010-08-03 2012-03-15 Fujifilm Corp Photoelectric converter, photoelectrochemical cell, and manufacturing methods of photoelectric converter and photoelectrochemical cell
WO2014084296A1 (en) 2012-11-30 2014-06-05 日本化薬株式会社 Dye-sensitized solar cell
CN109273602A (en) * 2018-09-10 2019-01-25 天津师范大学 Application of 2,2'-bipyridyl ligand metal organic hybrid materials in the field of optoelectronics

Also Published As

Publication number Publication date
JP5466943B2 (en) 2014-04-09
JPWO2009020098A1 (en) 2010-11-04

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