WO2007046452A1 - Colorant et pile solaire sensible aux colorants - Google Patents

Colorant et pile solaire sensible aux colorants Download PDF

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Publication number
WO2007046452A1
WO2007046452A1 PCT/JP2006/320809 JP2006320809W WO2007046452A1 WO 2007046452 A1 WO2007046452 A1 WO 2007046452A1 JP 2006320809 W JP2006320809 W JP 2006320809W WO 2007046452 A1 WO2007046452 A1 WO 2007046452A1
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group
dye
general formula
substituted
hydrogen atom
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PCT/JP2006/320809
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English (en)
Japanese (ja)
Inventor
Yong Wang
Kinji Yamada
Tetsuya Satou
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Jsr Corporation
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Publication of WO2007046452A1 publication Critical patent/WO2007046452A1/fr

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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
    • 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
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M14/00—Electrochemical current or voltage generators not provided for in groups H01M6/00 - H01M12/00; Manufacture thereof
    • H01M14/005—Photoelectrochemical storage 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
    • Y02E10/542—Dye sensitized solar cells

Definitions

  • the present invention relates to a dye and a dye-sensitized solar cell using the same.
  • dyes used in the above dye-sensitized solar cells include, for example, a dye called ⁇ 719] represented by the following formula (4), and a formula (5) There are dyes called “black dyes”, and these dyes are often used in dye-sensitized solar cells (for example, see Non-Patent Documents 1 and 2).
  • Patent Document 1 US Pat. No. 4,927,721
  • Patent Document 2 Pamphlet of International Publication No. 98Z50393
  • Non-Patent Document 1 Am. Chem. Soc., 115, 6382-6390 (1993)
  • Non-Patent Document 2 Am. Chem. Soc., 123, 1613-1624 (2001) Disclosure of the Invention
  • the power generation efficiency of the dye-sensitized solar cell is largely dependent on the dye, and the dye-sensitized solar cell using the dye still has sufficient power generation efficiency. Absent. Therefore, development of a dye-sensitized solar cell having sufficient power generation efficiency is required. That is, there is a demand for development of a dye for obtaining a dye-sensitized solar cell capable of obtaining sufficient power generation efficiency.
  • the present inventors have found that the dye represented by the following general formula (1) is high. It is extremely useful as a compound that can exhibit power generation efficiency. Dye-sensitized solar cells using this dye are
  • the inventors have found that the present invention has higher power generation efficiency than conventional dye-sensitized solar cells, and have made the present invention.
  • the present invention provides the following dye and a dye-sensitized solar cell using the dye.
  • M is an element of Group 8 to L0 on the long periodic table
  • L 1 is a bidentate ligand represented by the following general formula (2)
  • L 2 is It is a bidentate ligand represented by the following general formula (2) or the following general formula (3)
  • X 1 and X 2 are monovalent atomic groups or monodentate ligands
  • a 1 is a hydrogen atom, a carboxy group, a sulfonic acid group, a phosphoric acid group, or a salt thereof
  • R 1 and R 2 are a hydrogen atom or a monovalent organic group.
  • R 3 is a monovalent organic group or a hydrogen atom
  • one of R 4 and R 5 is a monovalent organic group
  • the other is a monovalent organic group or a hydrogen atom.
  • Each is an integer from 1 to 3)
  • R 6 and R 7 are a hydrogen atom or a monovalent organic group
  • m3 and m4 Are each independently an integer from 0 to 3
  • R 4 and R 5 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted group.
  • the pigment according to 2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted group.
  • a dye capable of producing a dye-sensitized solar cell having high power generation efficiency, and a dye-sensitized solar cell using the dye can be provided.
  • One embodiment of the dye of the present invention is represented by the following general formula (1). The details will be described below.
  • M is an element of Group 8 to L0 on the long periodic table
  • L 1 is a bidentate ligand represented by the following general formula (2)
  • L 2 is It is a bidentate ligand represented by the following general formula (2) or the following general formula (3)
  • X 1 and X 2 are monovalent atomic groups or monodentate ligands
  • a 1 is a hydrogen atom, a carboxy group, a sulfonic acid group, a phosphoric acid group, or a salt thereof
  • R 1 and R 2 are a hydrogen atom or a monovalent organic group.
  • R 3 is a monovalent organic group or a hydrogen atom
  • one of R 4 and R 5 is a monovalent organic group
  • the other is a monovalent organic group or a hydrogen atom.
  • Each is an integer from 1 to 3) [0024] [Chemical 8]
  • a 2 and A 3 are a carboxy group, a sulfonic acid group, a phosphoric acid group or a salt thereof, R 6 and R 7 are a hydrogen atom or a monovalent organic group, m 3 And m4 are each independently an integer of 0 to 3)
  • L 1 in the general formula (1) is a bidentate ligand represented by the general formula (2).
  • a 1 is a hydrogen atom, a carboxy group, a sulfonic acid group, a phosphoric acid group, or a salt thereof.
  • a hydrogen atom, a carboxy group, or a salt thereof is preferable. More preferably, it is a hydrogen atom.
  • a 1 is a salt
  • specific examples of counter force thione include ammonia ion, dimethylammonium ion, jetylammonium ion, tetramethylammonium ion, tetraethylammonium ion, tetrapropylammonium ion, Examples thereof include tetrabutyl ammonium ion, sodium ion, potassium ion, and the like.
  • R 1 in the general formula (2) is a hydrogen atom or a monovalent organic group.
  • the monovalent organic group include an alkyl group having 1 to 4 carbon atoms or an alkoxy group. Among these, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom or a methyl group is more preferable.
  • Ml represents an integer of 1 to 3.
  • R 2 is a hydrogen atom or a monovalent organic group.
  • the monovalent organic group include an alkyl group having 1 to 40 carbon atoms or an alkoxy group. Among these, an alkyl group having 1 to 24 carbon atoms is preferable.
  • M2 is an integer from 1 to 3 Represents.
  • R 2 is not particularly limited as long as it is a monovalent organic group, but when A 1 is a hydrogen atom, it is a monovalent organic group other than a carboxyl group, a sulfonic acid group, and a phosphoric acid group. It is preferable.
  • R 3 in the general formula (2) is a monovalent organic group or a hydrogen atom. Of these, an alkyl group or a hydrogen atom is preferred, and a methyl group, an ethyl group, or a hydrogen atom is particularly preferred.
  • One of R 4 and R 5 in the general formula (2) is a monovalent organic group, and the other is a hydrogen atom or a monovalent organic group.
  • R 4 and R 5 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, substituted or unsubstituted An unsubstituted alkylamino group and a substituted or unsubstituted arylyl group, an aryl group or a heteroaromatic group substituted with at least one selected group.
  • Particularly preferred are, for example, organic groups represented by the following general formulas (6-1) and (6-2).
  • Ar is a divalent aromatic hydrocarbon group or heteroaromatic group
  • X is a sulfur atom, oxygen atom or single bond
  • R 8 is a substituted or unsubstituted alkyl group, Or substituted or unsubstituted aryl group, wherein Ar is a divalent aromatic hydrocarbon group or heteroaromatic group, and one of R 9 and R 1C> is substituted or unsubstituted.
  • Ar in the general formulas (6-1) and (6-2) is a divalent aromatic hydrocarbon group or a heteroaromatic group.
  • the aromatic ring in the divalent aromatic hydrocarbon group or heteroaromatic group include a benzene ring, a naphthalene ring, an indene ring, and a furan ring. Of these, a group represented by the following formula (6-3) is particularly preferred.
  • R 8 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • an alkyl group, a phenyl group, a naphthyl group, or an alkoxyalkyl group is preferable.
  • the carbon number of R 8 is preferably 1 to 50, particularly preferably 1 to 12.
  • X in the general formula (6-1) is a sulfur atom, an oxygen atom or a single bond.
  • R 9 and R 1C> are one of a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and the other is a hydrogen atom, a substituted or unsubstituted alkyl group. Or a substituted or unsubstituted aryl group.
  • one is preferably an alkyl group or a phenyl group, and the other is preferably a hydrogen atom, an alkyl group, or a phenyl group.
  • R 4 and R 5 are a group represented by the general formula (6-1), the other is a hydrogen atom, and the general formula (6— It is particularly preferred that X in 1) is an oxygen atom or an R 8 cation group.
  • the dye of the present invention is first characterized by having a bidentate ligand represented by the general formula (2).
  • the bidentate ligand represented by the general formula (2) is characterized in that it has a substituted vinyl group in one pyridine ring of the biviridine skeleton.
  • the substituted vinyl group in the general formula (2) can be introduced into the biviridine skeleton using, for example, the Wittig reaction.
  • a phosphonium chloride derivative is synthesized by a reaction represented by the formula (8).
  • a bidentate ligand represented by the general formula (2) is obtained by reacting the synthesized phosphomuchloride derivative with a bipyridine compound having a carbonyl group or an aldehyde group. Can be synthesized.
  • a 1 in the general formula (2) is a carboxy group, a sulfonic acid group, a phosphoric acid group or a salt thereof, and A 1 in the formula (9) is the same, but a carboxy group, a sulfonic acid group, or a phosphoric acid It is also preferred that the group is a group protected with a protecting group. Alternatively, a group that easily becomes a carboxy group, a sulfonic acid group, or a phosphoric acid group by oxidation or the like, or a group that protects these groups is preferably A 1 in Formula (9). These groups can be converted into a carboxy group, a sulfonic acid group or a phosphoric acid group by deprotection and acid after completion of the reaction represented by the formula (9).
  • the bidentate ligand represented by the general formula (2) may be represented by the following formula (7) when A 1 is a hydrogen atom (hereinafter sometimes referred to as "second embodiment"). — 23) to (7- 43) The compound which has is mentioned.
  • the dye of the present invention may include a trans isomer, a cis isomer, and both of them. Of these, many are in the trans form.
  • the bidentate ligand represented by the general formula (2) has a substituted bur group in one pyridin ring in the biviridine skeleton, and a carboxy group, a sulfonic acid group, and a phosphorus group in the other pyridine ring.
  • a structure having an organic group other than an acid group is preferable.
  • the other pyridine ring has an organic group other than a carboxy group, a sulfonic acid group, and a phosphoric acid group, electron leakage to the electrolyte solution is prevented, so that there is an advantage that higher power generation efficiency can be obtained. is there.
  • the bidentate ligand represented by the general formula (2) is a substituted bull group in the general formula (2) using, for example, a dehydration reaction of alcohol. It can be synthesized by introducing it into the biviridine skeleton. For example, first, a biviridine derivative alcohol is synthesized. Next, the synthesized biviridine derivative alcohol is dehydrated using a salt by a reaction as shown in formula (10) to form olefin. In this way, the bidentate ligand represented by the general formula (2) can be synthesized. Even if A 1 is other than a hydrogen atom, as shown in Synthesis Example 3 to be described later, this method can be used to synthesize by first introducing a substituted vinyl group and then introducing the substituent A 1. Can do.
  • R ⁇ R 5 , ml and m2 are each in the general formula (2)! ⁇ 1 ⁇ ! ⁇ 5 , ml and m2 are supported.
  • L 2 in the general formula (1) is a bidentate ligand represented by the general formula (2) or the general formula (3).
  • General formula (2) has the above-described configuration.
  • a 2 and A 3 in the general formula (3) are each independently a carboxy group, a sulfonic acid group, a phosphoric acid group, or a salt thereof. Among these, a carboxy group or a salt thereof is preferable.
  • a 2 and A 3 are salts, the same ions as those mentioned as specific examples of the counter counter force thione of A 1 described above can be preferably used as the force counter cation.
  • R 6 and R 7 are a hydrogen atom or a monovalent organic group.
  • the organic acid include an alkyl group having 1 to 4 carbon atoms or an alkoxy group. Among these, a hydrogen atom or a methyl group is preferable.
  • M3 and m4 in the general formula (3) are each independently an integer of 1 to 3.
  • L 1 and L 2 are bidentate ligands in which L 1 is represented by the general formula (2), and L 2 is the general formula (2) or the general formula (3). As long as it is a bidentate ligand represented, there is no particular limitation!
  • the case where both of the forces L 1 and L 2 are represented by the above general formula (2) is also a preferred embodiment.
  • M in the general formula (1) is an element of group 8 to 10 on the long periodic table.
  • this element include iron, cobalt, nickel, ruthenium, osmium, iridium, platinum and the like. Among these, ruthenium is preferable.
  • X 1 and X 2 in the general formula (1) are a monovalent atomic group or a monodentate ligand.
  • Examples of the monovalent atomic group or monodentate ligand include atomic groups or ligands represented by the following formulas (11) to (17).
  • R 11 in the general formula (12) is preferably an alkyl group having 1 to 6 carbon atoms.
  • Ar in the general formulas (13) and (17) is an aryl group having 6 to 12 carbon atoms.
  • X 1 and X 2 in the general formula (1) are preferably those represented by the above general formula (2) (isothiocyanate) among the above atomic groups or ligands!
  • the dye of the present invention can be synthesized by synthesizing a ligand according to the formula (8) and the formula (9) or the formula (10), and then “Nat. Mater. 2, 402-407 (2003) ”.
  • the dye-sensitized solar cell of the present invention can suitably use the dye of the present invention.
  • the dye-sensitized solar cell of the present invention may have at least a cathode, an anode facing the cathode, and an electrolyte held between the cathode and the anode.
  • the cathode may have an oxide thin film electrode in which the above-described dye is chemically adsorbed on a transparent conductive glass.
  • the transparent conductive glass include tin oxide and indium-tin oxide ( ⁇ ).
  • Examples of the material constituting the oxide thin film electrode include titanium oxide, niobium oxide, zinc oxide, tin oxide, tungsten oxide, and indium oxide. Of these, titanium oxide, niobium oxide, and tin oxide are preferred, and titanium oxide is particularly preferred.
  • the method of forming the oxide thin film electrode For example, oxide fine particles to be an oxide thin film electrode are formed, suspended in an appropriate solvent, and applied onto transparent conductive glass. A method of heating after removing the solvent can be employed.
  • a transparent conductive film having an oxide thin film electrode on the surface obtained as described above can be used. It can be carried out by immersing the glass in a solution containing the pigment of the present invention.
  • the solvent that can be used here include jetyl ether, acetonitrile, ethanol, and the like.
  • the concentration of the dye solution is preferably 0.1 to: LOmmolZL.
  • As the soaking time 0.5 to: LOO time is preferred 2 to 50 hours is more preferred.
  • the temperature during the immersion is preferably 0 to 100 ° C, more preferably 10 to 50 ° C.
  • the anode is not particularly limited as long as it has electrical conductivity.
  • a material obtained by adhering a small amount of platinum or conductive carbon on transparent conductive glass can be suitably used.
  • the electrolyte for example, a solution containing a redox system, a solid, or an ionic liquid can be used. Specific examples thereof include, for example, a system using the following reaction of iodine (shown by Formula 18) as a redox system, and an electrolyte solution containing, for example, acetonitrile or propio-tolyl as a solvent. .
  • 4, 4- 1-dimethyl 1, 2, 2, 1-biviridine l lg was dissolved in 300 ml of tetrahydrofuran. Separately, 35 ml of lithium diisopropylamide solution (concentration 1.8 M, mixed solvent of tetrahydrofuran Z heptane Z ethylbenzene) and 3 ml of tetrahydrofuran were mixed and kept at ⁇ 78 ° C. To this solution, a tetrahydrofuran solution of 4,4′dimethyl-2,2′biviridine was added dropwise over 75 minutes while stirring at 78 ° C. under a nitrogen atmosphere. After completion of dropping, the mixture was further stirred for 15 minutes.
  • the temperature was raised to 0 ° C over 15 minutes with stirring, and then maintained at 0 ° C for 60 minutes.
  • the mixture was stirred while maintaining a temperature of 0 ° C under a nitrogen atmosphere, and 88 ml of tetrahydrofuran solution containing 7.5 ml of p-methoxybenzaldehyde was added dropwise over 60 minutes. Thereafter, the mixture was stirred for 120 minutes. Next, while stirring under a nitrogen atmosphere, the temperature was raised to room temperature over 90 minutes, and further stirred at room temperature for 12 hours.
  • Tetrahydrofuran was distilled off under reduced pressure at room temperature, 300 ml of dichloromethane and 500 ml of ion-exchanged water were added and stirred, and then the aqueous layer and the organic layer were separated.
  • the aqueous layer was extracted twice with 300 ml of dichloromethane, the extract and the organic layer were mixed, washed twice with 300 ml of ion-exchanged water, and dried by adding 22 g of magnesium sulfate. After drying, magnesium sulfate was filtered off, dichloromethane was distilled off under reduced pressure at room temperature, and further dried under reduced pressure at room temperature to obtain 2 lg of a yellow solid.
  • This solid was purified using a silica gel column under the conditions described later to obtain 9.8 g of product.
  • This product was analyzed by 1 H-NMR and found to be 4- [2- (4-methoxyphenyl) 2 -hydroxyethyl] -4'-methyl-2,2'-biviridine. — The result of NMR is shown below.
  • Silica gel lOOg was packed into a 200 ml column and the column was filled with black mouth form.
  • the above yellow solid was dissolved in 50 ml of black mouth form and applied to the above column. After developing with black mouth form, the volume was developed with 90.5 / 7.5 black mouth form Z methanol solvent and fractionated.
  • [0084] 4 was synthesized by the above (5, 5-dimethyl-1, 3 Jiokisa 2 cyclohexyl) one 4, one (4-methoxy-styryl) one 2, 2, - Bibirijin the mixture 814mg containing p- Torue Nsuruhon acid pyrid -15 mg of acetone, 160 ml of acetone and 40 ml of water were added and refluxed at 100 ° C for 12 hours. After the reaction, the mixture was concentrated with an evaporator and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated by an evaporator to obtain 440 mg of a mixture containing 2,2′bibilidine- 4 , ( 4 -methoxystyryl) -4 carboxaldehyde.
  • the powder was reprecipitated with dichloromethane-hexane solution and purified to obtain 6.7 g of the product.
  • the product was analyzed by 1 H-NMR and found to be 4- (N, N, 1 dimethylaminovinyl) 4, 1 (4-methoxystyryl) -2, 2, 1 biviridine. I understood. The results of H-NMR are shown below.
  • the formed precipitate was filtered off, and tetrahydrofuran was distilled off under reduced pressure at room temperature. After adding 10 Oml of dichloromethane and stirring, the aqueous layer and the organic layer were separated. The aqueous layer was extracted twice with 100 ml of dichloromethane, the extract and the organic layer were mixed, washed twice with 100 ml of saturated brine, and dried by adding lg of magnesium sulfate. After drying, magnesium sulfate was filtered off, dichloromethane was distilled off under reduced pressure at room temperature, and further dried under reduced pressure at room temperature to obtain 5.5 g of a yellow solid. The product was analyzed by 1 H-NMR and found to be 4 carbaldehyde -4 ′-(4-methoxystyryl) 2,2′-biviridine. The results of NMR are shown below.
  • Ethanol was distilled off under reduced pressure at room temperature, 1000 ml of a 6% dimethylformamide aqueous solution was added and stirred, and then the pH was adjusted to 3 with hydrochloric acid (concentration 1M). The resulting precipitate was collected by filtration and further dried under reduced pressure at room temperature to obtain 5.6 g of a black solid. This solid was purified using a silica gel column under the following conditions, and further purified by reprecipitation with a dimethylformamide-toluene solution to obtain 1.4 g of a product.
  • the conductive glass substrate for a cathode was pulled up and naturally dried for 2 hours to make this conductive glass substrate a cathode.
  • an anode conductive glass substrate is prepared, and platinum is deposited on this glass substrate. The anode was used.
  • an electrolyte solution containing 0.1 ImolZL iodine and 0.5 molZL lithium iodide in acetonitrile was prepared.
  • the surface of the cathode having the titanium oxide thin film and the surface of the anode on which platinum is deposited face inward, face each other at a distance of 0.1 mm, and sandwich the electrolyte solution therebetween (dye-sensitized solar cell) Battery cell).
  • a dye-sensitized solar cell (dye-sensitized solar cell) was produced in the same manner as in Example 5 except that the dye “T1” obtained in Example 2 was used, and the power generation efficiency was evaluated. It was confirmed that the dye-sensitized solar cell of this example had a power generation efficiency of 8.1%.
  • a dye-sensitized solar cell (dye-sensitized solar cell) was produced in the same manner as in Example 5 except that the dye “Tla” obtained in Example 3 was used, and the power generation efficiency was evaluated. It was confirmed that the power generation efficiency of the dye-sensitized solar cell of this example was 8.6%. [Example 8]:
  • a dye-sensitized solar cell (dye-sensitized solar cell) was produced in the same manner as in Example 5 except that the dye “T3” obtained in Example 4 was used, and the power generation efficiency was evaluated.
  • the dye-sensitized solar cell of this example was confirmed to have a power generation efficiency of 8.4%.
  • Dye sensitization was performed in the same manner as in Example 5 except that a commercially available dye “ ⁇ 719” (manufactured by Solaronix) was used as the dye having the structure represented by the above formula (4) instead of the dye “ ⁇ 2”.
  • a solar cell was produced and evaluated in the same manner as in “Evaluation of dye-sensitized solar cell” in Example 5. As a result, it was confirmed that the power generation efficiency was 6.1%.
  • the dye of the present invention and the dye-sensitized solar cell using this dye are excellent in power generation efficiency, they can be applied to various fields as a dye for solar cells and a solar cell.

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  • Power Engineering (AREA)
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Abstract

La présente invention concerne un colorant qui est représenté par la formule générale (1) ci-dessous et peut montrer une efficacité de génération de puissance élevée. ML1L2X1X2 (1) (Dans la formule générale (1), M représente un élément des groupes 8 à 10 du tableau périodique de forme longue ; L1 représente un ligand bidenté représenté par une certaine formule ; L2 représente un ligand bidenté représenté par la certaine formule mentionnée précédemment ou une formule différente de la certaine formule mentionnée précédemment ; et X1 et X2 représentent respectivement un groupe atomique monovalent ou un ligand monodenté).
PCT/JP2006/320809 2005-10-19 2006-10-19 Colorant et pile solaire sensible aux colorants WO2007046452A1 (fr)

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Cited By (3)

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US20120253043A1 (en) * 2009-09-29 2012-10-04 Ecole Polytechnique Federale De Lausanne (Epfl) Novel ligands for sensitizing dyes of dye-sensitized solar cells
CN101538416B (zh) * 2009-04-03 2013-09-18 新奥科技发展有限公司 金属有机染料、染料敏化电极、太阳能电池和反应器
CN106795377A (zh) * 2014-08-28 2017-05-31 株式会社东进世美肯 新型钌系染料及其制造方法

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CN102532005A (zh) * 2011-12-08 2012-07-04 河南省商业科学研究所有限责任公司 2,2’-联吡啶-4,4’-二甲醛的一步合成法

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EP1622178A1 (fr) * 2004-07-29 2006-02-01 Ecole Polytechnique Federale De Lausanne (Epfl) Ligands 2,2 -bipyridine, colorant sensibilisateur et pile solaire sensibilisee par un colorant

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EP1622178A1 (fr) * 2004-07-29 2006-02-01 Ecole Polytechnique Federale De Lausanne (Epfl) Ligands 2,2 -bipyridine, colorant sensibilisateur et pile solaire sensibilisee par un colorant

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CN101538416B (zh) * 2009-04-03 2013-09-18 新奥科技发展有限公司 金属有机染料、染料敏化电极、太阳能电池和反应器
US20120253043A1 (en) * 2009-09-29 2012-10-04 Ecole Polytechnique Federale De Lausanne (Epfl) Novel ligands for sensitizing dyes of dye-sensitized solar cells
US9359334B2 (en) * 2009-09-29 2016-06-07 Ecole Polytechnique Federale De Lausanne (Epfl) Ligands for sensitizing dyes of dye-sensitized solar cells
CN106795377A (zh) * 2014-08-28 2017-05-31 株式会社东进世美肯 新型钌系染料及其制造方法
CN106795377B (zh) * 2014-08-28 2019-07-19 株式会社东进世美肯 新型钌系染料及其制造方法

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