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WO2016136164A1 - Photosensibilisateur et élément de conversion photoélectrique - Google Patents

Photosensibilisateur et élément de conversion photoélectrique Download PDF

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Publication number
WO2016136164A1
WO2016136164A1 PCT/JP2016/000664 JP2016000664W WO2016136164A1 WO 2016136164 A1 WO2016136164 A1 WO 2016136164A1 JP 2016000664 W JP2016000664 W JP 2016000664W WO 2016136164 A1 WO2016136164 A1 WO 2016136164A1
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Prior art keywords
dye
group
photosensitizer
examples
photoelectric conversion
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Ceased
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PCT/JP2016/000664
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English (en)
Japanese (ja)
Inventor
由紀子 井上
伸治 東嶋
真吾 楮山
優太 鈴木
三浦　偉俊
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Chemicrea Inc
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Chemicrea Inc
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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
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • H10K85/652—Cyanine dyes
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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 photosensitizer and a photoelectric conversion element using the photosensitizer.
  • organic solar cells attracting attention as next-generation solar cells are roughly classified into organic thin film types and dye-sensitized types.
  • the organic thin film solar cell uses a pn junction made by combining organic materials, and the operation mechanism is exactly the same as that of the inorganic solar cell represented by silicon described above.
  • a dye-sensitized solar cell is characterized by using a modified electrode in which an organic dye is used as a photosensitizer and combined with an inorganic semiconductor such as titanium oxide or zinc oxide. Yes, it is a power generation system similar to photosynthesis.
  • DSC which should be called an inorganic / organic hybrid molecular device, has been put into practical use (Non-patent Document 1).
  • the working electrode of DSC has a simple structure in which a sensitizing dye is adsorbed on a conductive substrate obtained by sintering and laminating an inorganic semiconductor such as titanium oxide or zinc oxide.
  • the cell is completed by filling and sealing with an electrolytic solution or a cobalt-based electrolytic solution.
  • the DSC is easy to manufacture because of its simple structure. Special equipment such as a vacuum line is not required, and the cost can be reduced more easily than conventional solar cells.
  • the so-called Gretzell DSC is not only cheap in materials such as electrodes, but also does not require any special equipment investment, and is highly likely to realize a high cost reduction.
  • the electrode is made of porous titanium oxide with a high roughness factor made by high-temperature sintering of nanoparticles. By combining this with a ruthenium dye as a photosensitizer, it is now highly converted to over 12%. Efficiency has been achieved.
  • a general dye photosensitizer
  • a solvent for example, acetonitrile
  • a solvent with low solubility When a solvent with low solubility is used, a good adsorption state is not obtained on the semiconductor, and high conversion efficiency cannot be expected. For this reason, in order to achieve high conversion efficiency in various DSC preparations, it is strongly desired to develop dyes that are highly soluble in a wide range of solvents, particularly dyes that are highly versatile and inexpensive, such as hydrous alcohols. ing.
  • the present invention has been made in view of the above problems, has high solubility in solvents such as hydrous alcohol, has high adsorption power to electrodes such as titanium oxide or zinc oxide, has high conversion efficiency, and is durable
  • the object of the present invention is to provide a photosensitizer (novel organic dye) that is high in price and is inexpensive.
  • this invention aims at providing the photoelectric conversion element which has a light absorption layer containing this photosensitizer.
  • the dye represented by the following general formula (I) having an organic amine salt at the carboxyl group of the organic dye has high solubility in a solvent such as hydrous alcohol, and further, titanium oxide and oxidation. It has been found that the adsorption power to electrodes such as zinc is high and the conversion efficiency can be improved, and the invention has been completed.
  • the photosensitizer of the present invention is a salt of a dye represented by the following general formula (I), and more specifically has an amine salt at the carboxylic acid site of an organic dye.
  • n represents an integer of 1 or 2.
  • R 1 , R 2 and R 3 may be the same or different, and each represents a hydrogen atom, an alkyl group having 2 to 8 carbon atoms, or an aralkyl group.
  • R 1 , R 2 , and R 3 have at most one hydrogen atom, R 1 to R 3 may combine with each other to form a cyclic structure, and Dye does not contain a rare transition metal. Organic dye.
  • the photoelectric conversion element of the present invention is characterized by having a light absorption layer containing a photosensitizer represented by the above general formula (I).
  • the photosensitizer of the present invention has higher solubility in a wide range of solvents than conventional dyes, and can improve the conversion efficiency and improve the adsorption stability of the dye.
  • the mechanism of its action is not always clear, but a highly lipophilic organic amine forms a salt of appropriate strength at the carboxylic acid site that is the anchor. It is considered that it exhibits advantageous characteristics.
  • a conventional organic dye having a free carboxylic acid as an anchor is generally very crystalline, and it is necessary to use a solvent having a high dissolving power in the adsorption step.
  • organic amine salt of the carboxyl group of the dye of the present invention hereinafter also simply referred to as organic amine salt dye
  • the solubility in various solvents is significantly increased due to the highly lipophilic substituent of the amine as the counter anion. Therefore, it is considered that the solubility in a wide range of solvents such as hydrous alcohols is increased.
  • the salt of the dye represented by the general formula (I) is a metastable and moderately unstable salt, the chemical potential in the adsorption process is lowered, and it is more stable in the adsorption state on the electrode. It is thought that it becomes. For this reason, it is considered that the adsorptive power of the dye is improved, the coverage of the electrode surface is increased, and the adsorption orientation is also improved due to the influence of the highly lipophilic substituent, resulting in improved durability.
  • R 1 , R 2 and R 3 represent a hydrogen atom, an alkyl group having 2 to 8 carbon atoms, and an aralkyl group.
  • the alkyl group include an ethyl group
  • examples include linear alkyl groups such as propyl groups, branched alkyl groups such as isopropyl groups and isobutyl groups, and cyclic alkyl groups such as cyclopentyl groups and cyclohexyl groups.
  • These alkyl groups are further substituted with the substituents described below.
  • the aralkyl group include a benzyl group, a methoxybenzyl group, and a naphthylmethyl group, and these may be further substituted with a substituent described later.
  • Substituents include cyano group, isocyano group, thiocyanato group, isothiocyanato group, nitro group, nitrosyl group, sulfonyl group, halogen atom, hydroxyl group, phosphate ester group, substituted or unsubstituted mercapto group, substituted or unsubstituted amino group
  • a substituted or unsubstituted amide group, an alkoxy group, an alkoxyalkyl group, an alkoxycarbonyl group, an alkyl group, an aryl group, an aralkyl group, an acyl group, a heterocyclic residue, and the like are listed as examples, but are not particularly limited.
  • the halogen atom includes atoms such as chlorine, bromine and iodine
  • the phosphate ester group includes, for example, an alkyl phosphate (having 1 to 4 carbon atoms) ester group.
  • the substituted mercapto group include alkylthio groups such as methylthio and ethylthio.
  • substituted amino groups include mono- or dialkylamino groups, mono- or diarylamino groups, mono- or dimethylamino groups, mono- or diethylamino groups, mono- or dipropylamino groups, monophenylamino groups, or benzylamino groups.
  • the substituted amide group include an alkylamide group and an aromatic amide group.
  • alkoxy group examples include an alkoxy group (having 1 to 10 carbon atoms).
  • alkoxyalkyl group examples include a (carbon number 1 to 10) alkoxy (carbon number 1 to 4) alkyl group such as an ethoxyethyl group.
  • alkoxycarbonyl group examples include alkoxy (C1 to C10) carbonyl groups such as ethoxycarbonyl group. Examples of the alkyl group are the same as those described above.
  • aryl group examples include a phenyl group, a naphthyl group, an anthranyl group, a phenanthrenyl group, a pyrenyl group, an indenyl group, an azulenyl group, and a fluorenyl group, which may be further substituted with the above-described substituents.
  • acyl group for example, an alkylcarbonyl group having 1 to 10 carbon atoms and an arylcarbonyl group are preferable.
  • Examples of the aralkyl group are the same as those described above.
  • a heterocyclic residue means a group obtained by removing one hydrogen atom from a heterocyclic compound, such as pyridyl, pyrazyl, piperidyl, pyrazolyl, morpholyl, indolinyl, thiophenyl, furyl, oxazolyl, thiazolyl, indolyl, benzothiazolyl, benzo Examples thereof include oxazolyl, quinolyl, rhodanyl and the like, which may further have a substituent.
  • R 1 to R 3 may combine with each other to form a heterocyclic ring, and examples of the cyclic structure formed at that time include pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, quinuclidine, and the like. It may have a substituent and may further have a cyclic structure as a substituent.
  • Dye is an organic dye that does not contain a rare transition metal
  • the rare transition metal means a metal such as ruthenium, osmium, rhodium, iridium or rhenium, and zinc, magnesium, iron, cobalt, nickel or the like which is not a rare transition metal may be contained as a chelate metal.
  • R a in the following formula (II) represents an alkyl group, an aryl group, or an aralkyl group.
  • the alkyl group include a linear alkyl group such as a methyl group and an ethyl group, the aforementioned branched alkyl group, and a cyclic alkyl group, and these alkyl groups may be further substituted with the aforementioned substituents.
  • R b in the following formula (III) represents an alkyl group, an aryl group, or an aralkyl group, and examples thereof are the same as those described above.
  • the skeletons represented by the following formulas (II) and (III) may have substituents in other portions.
  • the substituent include an alkyl group, an aralkyl group, and a halogen atom, which may be combined with two substituents to form an aromatic ring.
  • Examples of the cyclic structure formed at that time include, for example, benzene, naphthalene, etc. These may further have a substituent, and may further have a cyclic structure as a substituent.
  • Examples of the alkyl group, aralkyl group and halogen atom are the same as those described above.
  • FIG. 1 is a schematic diagram showing one embodiment of a photoelectric conversion element of the present invention.
  • the photoelectric conversion element 1 includes a semiconductor layer 3 and an electrolyte layer 4 each having a light absorption layer formed by adsorbing a dye (photosensitizer of the present invention) to an oxide semiconductor layer on a substrate 2 having conductivity on the surface.
  • the counter electrode 5 is laminated
  • a support having a conductive property such as metal, or glass or plastic can be used as the support when the surface has conductivity.
  • a conductive layer tin-doped indium oxide (ITO), fluorine-doped tin oxide (FTO), gold, platinum, or a combination of these can be used, and this can be applied to a substrate by vacuum evaporation, A conductive layer is formed on the surface by directly forming the film by sputtering deposition, ion plating, chemical vapor deposition (CVD), or by attaching a film on which the film is formed to a substrate.
  • a conductive substrate can be formed.
  • oxide semiconductor examples include oxides such as titanium, tin, zinc, tungsten, zirconium, gallium, indium, yttrium, niobium, tantalum, and vanadium. Of these, oxides such as titanium, tin, zinc, niobium, and tungsten are preferable. Among these, (1) low cost, (2) easy formation of a porous body, and (3) conductivity as an electrode. From the viewpoints of properties, durability, stability and safety, and (4) compatibility of energy levels with the photosensitizer synthesized in the present invention, titanium and zinc oxides are preferable. These oxide semiconductors may be used alone or in combination of two or more.
  • An oxide semiconductor can be formed porous on a substrate by applying fine particles of the oxide semiconductor on the substrate and then heat-treating or electrodeposition with an electric furnace or microwave.
  • a method for adsorbing the dye to the oxide semiconductor layer a method such as immersing the substrate on which the oxide semiconductor layer is formed in a dye solution or a dye dispersion can be used. Can be formed.
  • the concentration of the solution can be appropriately determined depending on the dye, and specific examples of the solvent that can be used to dissolve the dye include, for example, methanol, ethanol, hydrous alcohol such as hydrous methanol and hydrous ethanol, ethyl acetate, methyl acetate, Preferred examples include tetrahydrofuran (THF), chloroform, acetonitrile, dimethyl sulfoxide, dimethylformamide (DMF), acetone, t-butanol and the like.
  • THF tetrahydrofuran
  • chloroform chloroform
  • acetonitrile dimethyl sulfoxide
  • DMF dimethylformamide
  • acetone t-butanol and the like.
  • a co-adsorbent may be added to the dye solution when adsorbing the dye on the thin film of oxide semiconductor fine particles.
  • the co-adsorbent include steroidal compounds such as cholic acid, crown ether, cyclodextrin, calixarene, polyethylene oxide, etc., but deoxycholic acid, dehydrocholic acid, cholic acid methyl ester, sodium cholate and the like are more preferable. preferable.
  • the electrolyte layer is a mixed liquid of acetonitrile and ethylene carbonate, a liquid electrolyte in which an electrolyte made of iodide such as metal iodine or lithium iodide is added using methoxypropionitrile as a solvent, a polymer gel electrolyte, etc. It can be formed using a solid electrolyte such as a solidified electrolyte, a p-type semiconductor, and a hole transport agent.
  • the counter electrode may be prepared in the same manner as the conductive substrate when transparency is required, or it may be prepared using carbon, a conductive polymer, a general metal, etc. when transparency is not required. be able to.
  • the organic amine salt dye of the present invention can be obtained by a method of isolating and purifying a salt using an excess organic base in the condensation reaction at the final stage of synthesis, or by allowing a suitable base to act once the dye is synthesized and isolated. It can be easily obtained by a method of forming a salt.
  • the photosensitizer of the present invention can also be used as a light absorption layer of an organic thin film solar cell.
  • the present invention will be described in more detail with reference to examples.
  • each dye shown in Examples 1 to 8 and Comparative Examples 1 to 3 was added, and the mixture was stirred at room temperature in a sealed state. When the dye was completely dissolved, additional dye was added. The saturation concentration was determined from the following formula from the amount of dye added when solids remained after 10 minutes from the addition of the dye. It was assumed that the change in the total volume due to the addition of the dye was negligibly small. The results are shown in Table 1.
  • the saturated concentrations in Table 1 were evaluated according to the following criteria. ⁇ : Saturation concentration 5000 ( ⁇ M) or more ⁇ : Saturation concentration 500 or more and less than 5000 ⁇ : Saturation concentration 50 or more and less than 500 ⁇ : Saturation concentration 50 or less
  • the organic amine salt dye of the present invention when using the organic amine salt dye of the present invention as compared with the existing organic dye having a free carboxylic acid as an anchor, not only a highly soluble solvent such as chloroform but also water content Improved solubility in low-solubility solvents such as alcohol. Although the mechanism of action is not necessarily clear, it is considered to be an effect of a substituent having a high fat solubility of the amine as a counter anion.
  • the concentration of the dye solution is also at a level that can be used as an adsorbing solvent during DSC preparation, and the organic amine salt dye of the present invention is very useful.
  • Tris- (2,2′-bipyridine) cobalt (II) di (tetracyanoborate) is 200 mM and tris- (2,2′-bipyridine) cobalt (III) tri (tetracyanoborate) is 40 mM with respect to acetonitrile.
  • An electrolyte solution was prepared by adding lithium tetrafluoroborate to 20 mM and N-butylbenzimidazole to 150 mM and dissolving them. This electrolyte solution was disposed between the counter substrate using the same FTO glass as the electrode base material and the above-described photoelectrode layer, thereby forming an electrolyte layer.
  • the organic amine salt dye of the present invention is used as the photosensitizer.
  • the photoelectric conversion efficiency was improved by about 2 to 7% as compared with the existing dye.
  • the organic amine salt dye of the present invention is used as a photosensitizer, compared with an existing dye having a corresponding free carboxylic acid. A further significant improvement in photoelectric conversion efficiency was observed at about 26%.
  • the organic amine salt dye of the present invention has high solubility in a solvent such as hydrous alcohol, and when used as a photosensitizer, improves the photoelectric conversion efficiency and adsorbs the dye. Stability can be improved. Further, the organic amine salt dye of the present invention can be taken out without purification by column chromatography, and can be said to be very useful from the viewpoint of synthesis. Furthermore, the amine used in the synthesis this time is very general and inexpensive, and is very useful in terms of cost.

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  • Engineering & Computer Science (AREA)
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Abstract

[Problème] Fournir un photosensibilisateur qui présente une solubilité élevée dans un solvant tel qu'un alcool hydraté, tout en ayant une efficacité de conversion et une durabilité excellentes. [Solution] Un photosensibilisateur qui est un sel d'un colorant représenté par la formule générale (I). (Dans la formule (I), n représente un nombre entier de 1 ou 2 ; R1, R2 et R3 peuvent être identiques ou différents l'un de l'autre, et chacun représente un atome d'hydrogène, un groupe alkyle ayant 2 à 8 atomes de carbone ou un groupe aralkyle, une fraction parmi les fractions R1, R2 et R3 étant un atome d'hydrogène au maximum ; les fractions 1, R2 et R3 pouvant se combiner ensemble pour former une structure cyclique ; et le colorant représente un colorant organique ne contenant pas de métal de transition rare. )
PCT/JP2016/000664 2015-02-27 2016-02-09 Photosensibilisateur et élément de conversion photoélectrique Ceased WO2016136164A1 (fr)

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JP2015039110A JP2016160321A (ja) 2015-02-27 2015-02-27 光増感剤および光電変換素子
JP2015-039110 2015-02-27

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Publication number Priority date Publication date Assignee Title
JP7341946B2 (ja) * 2019-12-11 2023-09-11 三菱製紙株式会社 蛍光変換媒体

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006028087A1 (fr) * 2004-09-08 2006-03-16 Nippon Kayaku Kabushiki Kaisha Dispositifs de conversion photoélectriques sensibilisés par teinture
WO2007100033A1 (fr) * 2006-03-02 2007-09-07 Nippon Kayaku Kabushiki Kaisha Dispositif de conversion photoelectrique sensible aux colorants
JP2010031204A (ja) * 2008-07-31 2010-02-12 Kemikurea:Kk 光増感剤および光電変換素子
JP2012114035A (ja) * 2010-11-26 2012-06-14 Mitsubishi Paper Mills Ltd 光電変換材料、半導体電極およびそれを用いた光電変換素子
JP2013035936A (ja) * 2011-08-08 2013-02-21 Kemikurea:Kk 光増感剤および光電変換素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006028087A1 (fr) * 2004-09-08 2006-03-16 Nippon Kayaku Kabushiki Kaisha Dispositifs de conversion photoélectriques sensibilisés par teinture
WO2007100033A1 (fr) * 2006-03-02 2007-09-07 Nippon Kayaku Kabushiki Kaisha Dispositif de conversion photoelectrique sensible aux colorants
JP2010031204A (ja) * 2008-07-31 2010-02-12 Kemikurea:Kk 光増感剤および光電変換素子
JP2012114035A (ja) * 2010-11-26 2012-06-14 Mitsubishi Paper Mills Ltd 光電変換材料、半導体電極およびそれを用いた光電変換素子
JP2013035936A (ja) * 2011-08-08 2013-02-21 Kemikurea:Kk 光増感剤および光電変換素子

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