CN104053651A - 新型化合物及担载有该新型化合物的担载体 - Google Patents
新型化合物及担载有该新型化合物的担载体 Download PDFInfo
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- CN104053651A CN104053651A CN201380005148.8A CN201380005148A CN104053651A CN 104053651 A CN104053651 A CN 104053651A CN 201380005148 A CN201380005148 A CN 201380005148A CN 104053651 A CN104053651 A CN 104053651A
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- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 230000001235 sensitizing effect Effects 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical group [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
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- 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
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- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- 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
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- 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
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- 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
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- 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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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
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Abstract
本发明涉及下述通式(1)所示的新型化合物、将该新型化合物担载于载体上而成的担载体及使用了该担载体的光电转换元件。式中,Z为C1~50的共轭性基团,R1表示被羧基、氰基、氨基、酰胺基或硝基取代了的C6~20的芳香族烃基、被脂肪族烃基取代了的C7~20的芳香族烃基或C1~20的脂肪族烃基,该脂肪族烃基可以被-O-等中断,R2表示氢原子或可被取代的C1~20的烃基,R30~R33、R40~R44表示氢原子或可被取代的烃基,它们可以连接形成环,R5表示氢原子或氰基,R11为表示下述部分结构式(11-1)或(11-2)所示的基团,式中的n、环A等的定义参见说明书。
Description
技术领域
本发明涉及新型化合物、将该新型化合物担载于载体而成的担载体及使用了该担载体的光电转换元件。
背景技术
一直以来,在多种多样的技术领域中广泛使用色素。举其一例时,在太阳能电池等光电转换元件的领域中,具有光增感作用的色素被用于色素增感型光电转换元件中。该色素增感型光电转换元件理论上可期待高效率,相比较于使用了以往的硅半导体的光电转换元件,认为能够以低成本进行制造。
色素增感型光电转换元件具有带有使用了色素的载体的氧化物半导体的电极。该色素增感型光电转换元件中,色素将入射到元件的光吸收而被激发,被激发的色素将电子注入到载体中,从而进行光电转换。
作为提高色素增感型光电转换元件的转换效率及耐久性的手法,探讨了提高载体和色素的担载性。即,通过提高物理和/或化学的吸附性,能够使色素的激发能量以高效率移动至载体,还可以抑制色素溶出至元件中(具体地说是溶出至电解液等中)。作为提高担载性的手法,公开了使色素分子具有羧酸基发生酰胺键合而成的结构的手法(专利文献1)、使色素分子具有2个羧基的手法(专利文献2)等。
就作为色素增感型光电转换元件的主要用途之一的太阳能电池而言,在其用途的特性方面要求高的耐久性,而公知的色素及使用了该色素的光电转换元件仍无法获得充分的特性。
现有技术文献
专利文献
专利文献1:日本特开2011-122088号公报
专利文献2:日本特开2000-299139号公报
发明内容
发明要解决的技术问题
因此,本发明的目的在于提供新型化合物、特别是作为对载体显示出高吸附性的色素的新型化合物、将该新型化合物担载于载体而成的担载体及高效率和高耐久性的光电转换元件。
用于解决技术问题的方法
本发明人们深入研究的结果发现了具有特定结构的新型化合物,该化合物可达成上述目的,从而完成了本发明。
即,本发明提供下述通式(1)所示的新型化合物、担载有该化合物的担载体及具备具有该担载体的电极的光电转换元件。
(式中,Z为不饱和脂肪族烃基、芳香族烃基、芳香族杂环基或这些基团中的1种或2种以上连接而成的碳原子数为1~50的共轭性基团,
R1表示被羧基、氰基、氨基、酰胺基或硝基中的至少1个取代了的碳原子数为6~20的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~20的芳香族烃基或碳原子数为1~20的脂肪族烃基,该脂肪族烃基还可以被-O-、-COO-、-OCO-、-NR24-、-NR24COO-或-OCONR24-中断1~3次,当被中断2次以上时,中断的基团不相邻,R24表示被羧基、氰基、氨基、酰胺基或硝基取代的或未被取代的碳原子数为6~10的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~15的芳香族烃基或碳原子数为1~10的脂肪族烃基,
R2表示氢原子或可被取代的碳原子数为1~20的烃基,R30、R31、R32、R33、R40、R41、R42、R43及R44各自独立地表示氢原子或可被取代的烃基,R30与R31、R40与R41、R41与R42、R42与R43、R33与R44还可分别连接形成环,
R5表示氢原子或氰基,
R11为下述部分结构式(11-1)或(11-2)所示的基团。)
(式中,n表示1~4的整数,
环A表示苯环、萘环、环己烷环、环己烯环或环己二烯环,
式中的除羧基的氢原子以外的氢原子可被羧基、氰基、氨基、酰胺基、硝基或被这些基团取代了的碳原子数为1~4的脂肪族烃基或者碳原子数为1~4的无取代脂肪族烃基所取代。)
发明效果
本发明的新型化合物由于具有羧基及上述R1所示的基团,因此会提供吸附性优异、并且高效率、高耐久的担载体及电极,适于太阳能电池等光电转换元件。
附图说明
图1为表示本发明的光电转换元件之一例的截面构成的示意图。
图2为图1所示的本发明的光电转换元件的主要部分的放大图。
具体实施方式
以下根据优选的实施方式说明本发明的新型化合物、本发明的担载体及使用该担载体而成的光电转换元件。
首先,对本发明的新型化合物进行说明。
上述通式(1)中的Z所表示的共轭性基团只要是π共轭基团则无特别限定,也可以具有取代基。本发明中,π共轭基团是表示不饱和键相连而形成,Z所表示的π共轭基团中,从在后说明的光电转换元件的转换效率增高的方面出发,优选相连形成的不饱和键的碳原子数为4~60、更优选为4~40。
作为Z所表示的基团,优选是选自下述式(Z-1)~(Z-10)所示基团中的基团连接了1~7个而成的基团,其中更优选具有至少1个(Z-7)所示的基团、特别优选仅由(Z-7)构成。
(式中,X表示S、O、NR6或SiR6R7,式中的氢原子(但直接键合于氮原子的氢原子除外)可以被氟原子、氯原子、碘原子、氰基、硝基、-OR6基、-SR6基、-NR6R7基、-SiR6R7R8基或可被取代的脂肪族烃基取代,R6、R7及R8表示氢原子或可被取代的烃基。)
作为取代上述式(Z-1)~(Z-10)中的氢原子的脂肪族烃基,例如可举出甲基、乙基、丙基、异丙基、环丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、环戊基、己基、2-己基、3-己基、环己基、二环己基、1-甲基环己基、庚基、2-庚基、3-庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基、壬基、异壬基、癸基等烷基;甲基氧基、乙基氧基、丙基氧基、异丙基氧基、丁基氧基、仲丁基氧基、叔丁基氧基、异丁基氧基、戊基氧基、异戊基氧基、叔戊基氧基、己基氧基、环己基氧基、庚基氧基、异庚基氧基、叔庚基氧基、正辛基氧基、异辛基氧基、叔辛基氧基、2-乙基己基氧基、壬基氧基、癸基氧基等烷氧基;甲基硫基、乙基硫基、丙基硫基、异丙基硫基、丁基硫基、仲丁基硫基、叔丁基硫基、异丁基硫基、戊基硫基、异戊基硫基、叔戊基硫基、己基硫基、环己基硫基、庚基硫基、异庚基硫基、叔庚基硫基、正辛基硫基、异辛基硫基、叔辛基硫基、2-乙基己基硫基等烷基硫基;乙烯基、1-甲基乙烯基、2-甲基乙烯基、2-丙烯基、1-甲基-3-丙烯基、3-丁烯基、1-甲基-3-丁烯基、异丁烯基、3-戊烯基、4-己烯基、环己烯基、二环己烯基、庚烯基、辛烯基、癸烯基、十五碳烯基、二十碳烯基、二十三碳烯基等链烯基等,这些基团还可在氧原子和/或氮原子不相邻的条件下被-O-、-CO-、-COO-、-OCO-、-NHCO-、-NH-、NHCO-中断1~4次。该脂肪族烃基还可被氟原子、氯原子、碘原子、氰基、硝基、羟基、硫醇基或氨基进一步取代。
作为上述R6及R7所表示的可被取代的烃基,可举出脂肪族烃基、脂环式烃基、芳香族烃基及这些基团多个键合而成的基团,作为脂肪族烃基,可以举出作为取代(Z-1)~(Z-10)中的氢原子的脂肪族烃基而在上述中说明过的基团,作为脂环式烃基,可举出环丙基、环戊基、环己基、环庚基等,作为芳香族烃基,可举出苯基、萘基、苄基、芴基、茚基等。
作为上述R6及R7所表示的可被取代的烃基上的取代基,可举出氟原子、氯原子、碘原子、氰基、硝基、羟基、硫醇基或氨基。
对上述通式(1)中的R1进行说明。
作为碳原子数为6~20的芳香族烃基,可举出苯基、萘基、环己基苯基、联苯基、联三苯基、芴基、硫代苯基苯基、呋喃基苯基、2'-苯基-丙基苯基、苄基、萘基甲基等,这些基团被羧基、氰基、氨基、酰胺基、硝基取代至少1个,作为这种基团,可举出2-羧基苯基、3-羧基苯基、4-羧基苯基、2-氰基苯基、3-氰基苯基、4-氰基苯基、2-氨基苯基、3-氨基苯基、4-氨基苯基、苯基酰胺-4'-基、2-硝基酰胺、3-硝基酰胺、4-硝基酰胺、3-羧基萘、4-羧基萘、5-羧基萘、6-羧基萘、6-羧基萘-2-基、3-氰基萘、4-氰基萘、5-氰基萘、4-羧基苯基甲基、4-氰基苯基甲基等。
作为碳原子数为1~20的脂肪族烃基,可举出与作为取代(Z-1)~(Z-10)中的氢原子的脂肪族烃基而在上述中列举过的相同的基团,这些基团被羧基、氰基、氨基、酰胺基、硝基取代至少1个,作为这种基团,可举出氰基甲基、2-氰基乙基、2-氰基丙基、3-氰基丙基、羧基甲基、2-羧基乙基、2-羧基丙基、3-羧基丙基、甲基酰胺、乙基酰胺、硝基甲基、2-硝基乙基、3-硝基丙基等。
作为被脂肪族烃基取代了的碳原子数为7~20的芳香族烃基,可以举出上述所列举的芳香族烃基被上述脂肪族烃基取代了的基团,这些基团被羧基、氰基、氨基、酰胺基、硝基取代至少1个,作为这种基团,可举出2-羧基-5-甲基苯基、5-羧基-2-甲基苯基、4-羧基-2,5-二甲基苯基、4-氰基-2,5-二甲基苯基等。
R1中必须含有的羧基、氰基、氨基、酰胺基、硝基为1~3个,优选为1或2个,特别优选为1个。羧基、氰基、氨基、酰胺基、硝基中,优选羧基、氰基,更优选羧基。
作为上述通式(1)中R2所表示的碳原子数为1~20的可被取代的烃基,可以举出在作为R6所表示的可被取代的烃基所列举的基团中碳原子数为1~20的基团。作为R30、R31、R32、R33、R40、R41、R42、R43及R44所表示的可被取代的烃基,可举出与作为R6所表示的可被取代的烃基所列举的基团相同的基团。
R30与R31、R40与R41、R41与R42、R42与R43、R33与R44可分别连接形成环,作为所形成的环的例子,可举出苯环、二噁烯环等。
上述通式(1)中,优选R5为氰基或者R11为上述部分结构式(11-1)所示的基团、n为1或2的化合物,更优选R5为氰基、R11为上述部分结构式(11-1)所示的基团、n为1或2的化合物。
另外,上述通式(1)所示的化合物还优选为下述通式(2)所示的化合物。
(式中,Z、R1、R11、R2、R30、R31、R32、R40、R41、R42、R43及R5与上述通式(1)中的含义相同。)
作为上述通式(1)所示的新型化合物的具体例子,可举出以下的No.1~42的化合物,但并非限定于这些。其中,式中Hex表示己基。
本发明的通式(1)所示的化合物可通过利用公知或周知的通常反应的方法获得,其合成方法并无特别限定。若举出代表性合成方法的一例,可以通过将具有羧酸基的共轭体的羧酸(10)转换成酰氯(11)之后与羧基得到了保护的仲胺化合物(12)反应,从而合成酰胺体(13),通过利用三氟乙酸进行脱保护,从而合成上述通式(1)所示的化合物(以下例中是R11为上述部分结构式(11-1)所示化合物的下述通式(1’)所示的化合物)。另外,反应中使用的试剂还可根据需要进行变更。
(式中,Z、R1、R2、R30、R31、R32、R33、R40、R41、R42、R43、R44、R5及n与上述通式(1)中的含义相同。)
本发明的新型化合物如在后说明的那样,可以使其担载于载体以担载体的形态优选地用于光电转换元件等用途。本发明的新型化合物除此之外还可用于光学记录材料、医药品、农药、香料、染料等合成中间体;各种功能性材料、各种聚合物原料;光电化学电池、非线形光学装置、电致色变显示器、全息图、有机半导体、有机EL;卤化银照片感光材料、光增感剂;印刷油墨、喷墨、电子照片彩色色调剂、化妆品、塑料等中使用的着色剂;蛋白质用染色剤、用于物质检测的发光染料;合成石英原料、涂料、合成催化剂、催化剂载体、表面涂覆薄膜材料、有机硅橡胶交联剂、粘合剂等用途中。
接着,对本发明的担载体进行说明。
作为本发明的担载体中使用的材料(载体),可举出丙烯酸树脂、含氟树脂等有机树脂,氧化钛、氧化锌、氧化铝等金属氧化物,氧化硅、沸石、活性炭等,优选表面为多孔质的材料。作为所担载的化合物,其特征在于,其为上述通式(1)所示的化合物。作为使该化合物担载于载体的方法,可以使用公知的气层吸附、液层吸附等方法,例如作为液层吸附的例子,可举出将本发明的化合物溶解在溶剂中、通过将上述载体浸渍在该溶液中来使其吸附的方法。
上述载体的形状并无特别限定,例如根据担载体的用途从膜状、粉状、粒状等形状中适当选择即可。另外,对于上述载体的大小及本发明担载体中的本发明化合物的担载量也并无特别限定,根据担载体的用途适当选择即可。
担载有本发明新型化合物的本发明的担载体除了优选地用于以下说明的光电转换元件之外,还可用于催化剂、色调剂等中。
接着,对本发明的光电转换元件进行说明。
本发明的光电转换元件是色素增感型光电转换元件,除了使用本发明的新型化合物作为色素的方面之外,可以与现有的色素增感型光电转换元件相同。以下参照图1及图2说明本发明的光电转换元件的代表性构成例。
图1为示意地表示本发明的光电转换元件之一例的截面构成的图,图2为将图1所示的光电转换元件的主要部分摘出后放大显示的图。图1及图2所示的光电转换元件是所谓的色素增感型太阳能电池的主要部分。该光电转换元件是将工作电极10与对置电极20隔着电解质含有层30相向配置而成的,工作电极10及对置电极20中的至少一者是具有透光性的电极。
工作电极10例如具有导电性基板11、设置于其一个面(对置电极20一侧的面)上的金属氧化物半导体层12和担载于金属氧化物半导体层12的色素13。本发明的光电转换元件中,色素13是上述通式(1)所示的本发明的新型化合物,作为色素的本发明的新型化合物与担载其的金属氧化物半导体层12的复合体即是本发明的担载体。
工作电极10针对外部电路作为负极发挥功能。导电性基板11例如在绝缘性基板11A的表面上设有导电层11B。
作为基板11A的材料,例如可举出玻璃、塑料等绝缘性材料。塑料例如以透明聚合物膜的形态使用,作为形成透明聚合物膜的塑料,例如可举出四乙酰纤维素(TAC)、聚对苯二甲酸乙二醇酯(PET)、聚萘二甲酸乙二醇酯(PEN)、间同立构聚苯乙烯(SPS)、聚苯硫醚(PPS)、聚碳酸酯(PC)、聚丙烯酸酯(PAR)、聚砜(PSF)、聚酯砜(PES)、聚醚酰亚胺(PEI)、环状聚烯烃或溴化苯氧树脂等。
作为导电层11B,例如可举出含有氧化铟、氧化锡、铟-锡复合氧化物(ITO)或在氧化锡中掺杂有氟的物质(FTO:F-SnO2)等的导电性金属氧化物薄膜或者含有金(Au)、银(Ag)或铂(Pt)等的金属薄膜及金属筛、用导电性高分子等形成的导电层等。
另外,导电性基板11例如可通过具有导电性的材料、按照变为单层结构的方式构成,此时作为导电性基板11的材料,例如可举出氧化铟、氧化锡、铟-锡复合氧化物或在氧化锡中掺杂有氟的物质等导电性金属氧化物或者金、银或铂等金属、导电性高分子等。
金属氧化物半导体层12是担载色素13的载体,例如如图2所示具有多孔质结构。金属氧化物半导体层12由致密层12A和多孔质层12B形成。致密层12A优选在与导电性基板11的界面处形成、是致密且空隙少的层,更优选为膜状。多孔质层12B优选在与电解质含有层30相接触的表面处形成、是空隙多且表面积大的结构,特别是更优选为附着有多孔质的微粒的结构。此外,金属氧化物半导体层12例如还可按照成为膜状的单层结构的方式来形成。本发明中,担载是指色素13与多孔质层12B发生化学的、物理的或电的结合或吸附的状态。
作为金属氧化物半导体层12中含有的材料(金属氧化物半导体材料),例如可举出氧化钛、氧化锌、氧化锡、氧化铌、氧化铟、氧化锆、氧化钽、氧化钒、氧化钇、氧化铝或氧化镁等。其中,作为金属氧化物半导体材料,为了获得高的转换效率,优选氧化钛及氧化锌。另外,这些金属氧化物半导体材料可单独使用任意1种,还可使2种以上复合(混合、混晶、固溶体、表面被覆等)来使用,例如还可以以氧化钛及氧化锌等的组合来使用。
作为具有多孔质结构的金属氧化物半导体层12的形成方法,例如可举出电解析出法、涂布法或烧成法等。利用电解析出法形成金属氧化物半导体层12时,在含有金属氧化物半导体材料的微粒的电解浴液中,使该微粒附着在导电性基板11的导电层11B上,同时使金属氧化物半导体材料析出。利用涂布法形成金属氧化物半导体层12时,将分散有金属氧化物半导体材料的微粒的分散液(金属氧化物浆料)涂布在导电性基板11上之后,使其干燥以将分散液中的分散介质除去。利用烧结法形成金属氧化物半导体层12时,与涂布法同样地将金属氧化物浆料涂布在导电性基板11上并进行干燥后进行烧成。此外,如果利用电解析出法或涂布法形成金属氧化物半导体层12,则可以使用耐热性低的塑料材料或聚合物膜材料作为基板11A,因此可以制作挠性高的电极。
另外,金属氧化物半导体层12还可使用有机碱、尿素衍生物、环状糖链进行处理。作为有机碱,可举出二芳基胺、三芳基胺、吡啶、4-叔丁基吡啶、聚乙烯基吡啶、喹啉、哌啶、脒等有机碱。该处理可以是在吸附下述说明的色素13之前、也可以是在吸附下述说明的色素13之后来进行。作为处理方法,可举出浸渍处理,处理剂为固体时,在溶解于有机溶剂后进行浸渍处理即可。
色素13含有例如对金属氧化物半导体层12发生吸附、通过吸收光而被激发、从而将电子注入到金属氧化物半导体层12中的1种或2种以上的色素(增感色素)。本发明的光电转换元件中,上述通式(1)所示的本发明的新型化合物相当于色素13。使用本发明的新型化合物作为色素13时,作为色素13整体,相对于所照射的光量的向金属氧化物半导体层12中的电子注入量的比例增高,因此转换效率提高。
色素13含有至少1种的上述通式(1)所示的本发明的新型化合物即可,还可含有其他的色素。作为其他的色素,可举出有机色素(以下称作其他的有机色素)及有机金属配位化合物,优选具有能够吸附于金属氧化物半导体层12(载体)的基团的色素。
作为其他的有机色素,可举出曙红Y、二溴荧光素、荧光素、若丹明B、焦棓酚、二氯荧光素、赤藓红B(赤藓红为注册商标)、荧光生、红汞、花青系色素、部花青双偶氮系色素、三唑系色素、蒽醌系色素、多环醌系色素、靛蓝系色素、二苯基甲烷系色素、三甲基甲烷系色素、喹啉系色素、二苯甲酮系色素、萘醌系色素、二萘嵌苯系色素、芴酮系色素、方酸菁系色素、薁鎓系色素、紫环酮系色素、喹吖酮系色素、无金属酞菁系色素、无金属卟啉系色素或无金属氮杂卟啉系色素等。
作为有机金属配位化合物,可举出具有由位于芳香族杂环内的氮阴离子与金属阳离子形成的离子性配位键和在氮原子或硫属原子与金属阳离子之间形成的非离子性配位键这两者的有机金属配位化合物、具有由氧阴离子或硫阴离子与金属阳离子形成的离子性配位键和在氮原子或硫属原子与金属阳离子之间形成的非离子性配位键这两者的有机金属配位化合物等。具体地可举出铜酞菁、氧钛酞菁、钴酞菁、镍酞菁、铁酞菁等金属酞菁系色素、金属萘酞菁系色素、金属卟啉系色素、金属氮杂卟啉系色素以及使用了钌、铁、锇的联吡啶金属配位体、三吡啶金属配位体、菲绕啉金属配位体、二喹啉甲酸金属配位体、偶氮金属配位体或喹啉酚金属配位体等的钌配位体等。
另外,色素13除了上述色素之外,还可含有1种或2种以上的添加剂。作为该添加剂,例如可举出抑制色素中的化合物的缔合的缔合抑制剂,具体地为化学式(14)所示的胆酸系化合物等。它们可单独使用,也可混合多种使用。
(式中,R91为具有酸性基团或烷氧基甲硅烷基的烷基。R92表示与构成化学式中的甾类化合物骨架的碳原子的任一个键合的基团,是羟基、卤基、烷基、烷氧基、芳基、杂环基、酰基、酰氧基、氧基羰基、氧基、酸性基团或烷氧基甲硅烷基或者它们的衍生物,它们可相同也可不同。t为1以上5以下的整数。构成化学式中的甾类化合物骨架的碳原子与碳原子之间的键可以是单键、也可以是双键。)
对置电极20例如在导电性基板21上设有导电层22,针对外部电路作为正极发挥功能。作为导电性基板21的材料,例如可以举出与工作电极10的导电性基板11的基板11A的材料相同的材料。导电层22含有1种或2种以上的导电材料和根据需要的粘合材料而构成。作为导电层22中使用的导电材料,例如可举出铂、金、银、铜(Cu)、铑(Rh)、钌(Ru)、铝(Al)、镁(Mg)或铟(In)等金属、碳(C)或导电性高分子等。另外,作为导电层22中使用的粘合材料,可举出丙烯酸树脂、聚酯树脂、酚醛树脂、环氧树脂、纤维素、蜜胺树脂、氟弹性体或聚酰亚胺树脂等。此外,对置电极20例如也可以是导电层22的单层结构。
电解质含有层30例如含有具有氧化还原对的氧化还原电解质而构成。作为氧化还原电解质,例如可举出I-/I3 -系、Br-/Br3 -系、醌/氢醌系、Co配位体系或硝酰自由基化合物系等。具体地说为组合了碘化物盐与碘单质的电解质、或组合了溴化物盐与溴单质的电解质等组合了卤化物盐和卤素单质的电解质等。作为该卤化物盐,可举出卤化铯、卤化烷基季铵盐类、卤化咪唑鎓类、卤化噻唑鎓类、卤化噁唑鎓类、卤化喹啉鎓类或卤化吡啶鎓类等。具体地说,作为碘化物盐,例如可举出碘化铯、四乙基碘化铵、四丙基碘化铵、四丁基碘化铵、四戊基碘化铵、四己基碘化铵、四庚基碘化铵或三甲基苯基碘化铵等烷基季铵盐碘化物类、或者3-甲基咪唑碘或1-丙基-2,3-二甲基咪唑碘等咪唑碘类,3-乙基-2-甲基-2-噻唑碘、3-乙基-5-(2-羟基乙基)-4-甲基噻唑碘或3-乙基-2-甲基苯并噻唑碘等噻唑碘类,3-乙基-2-甲基-苯并噁唑碘等噁唑碘类,1-乙基-2-甲基喹啉碘等喹啉碘类,吡啶碘类等。另外,作为溴化物盐,例如可举出烷基季铵盐溴化物等。在组合了卤化物盐与卤素单质的电解质中,优选上述碘化物盐中的至少1种与碘单质的组合。
另外,氧化还原电解质例如还可以是组合了离子性液体与卤素单质的电解质。此时,还可进一步含有上述卤化物盐等。作为离子性液体,可举出在电池或太阳能电池等中可以使用的离子性液体,例如可举出在“Inorg.Chem”1996,35,p1168~1178、《Electrochemistry》2002,2,p130~136、US5728487A或US5683832A等中公开的离子性液体。其中,作为离子性液体,优选是具有低于室温(25℃)的熔点的盐、或者即便具有高于室温的熔点但通过与其他的熔融盐等相熔解而在室温下发生了液化的盐。作为该离子性液体的具体例子,可举出以下所示的阴离子及阳离子等。
作为离子性液体的阳离子,例如可举出铵、咪唑鎓、噁唑鎓、噻唑鎓、噁二唑鎓、三唑鎓、吡咯烷鎓、吡啶鎓、哌啶鎓、吡唑鎓、嘧啶鎓、吡嗪鎓、三嗪鎓、鏻、锍、咔唑鎓、吲哚鎓或它们的衍生物。它们可单独使用,也可混合多种使用。具体地可举出1-甲基-3-丙基咪唑鎓、1-丁基-3-甲基咪唑鎓、1,2-二甲基-3-丙基咪唑鎓或1-乙基-3-甲基咪唑鎓等。
作为离子性液体的阴离子,可举出AlCl4 -或Al2Cl7 -等金属氯化物、或者PF6 -、BF4 -、CF3SO3 -、N(CF3SO2)2 -、F(HF)n -或CF3COO-等含氟物离子、或者NO3 -、CH3COO-、C6H11COO-、CH3OSO3 -、CH3OSO2 -、CH3SO3 -、CH3SO2 -、(CH3O)2PO2 -、N(CN)2 -或SCN-等非氟化合物离子、或者碘化物离子或溴化物离子等卤化物离子。它们可单独使用、也可混合多种使用。其中,作为该离子性液体的阴离子,优选碘化物离子。
电解质含有层30中可以使用在溶剂中溶解有上述氧化还原电解质的液状的电解质(电解液),也可使用在高分子物质中保持了电解液的固体高分子电解质。另外,还可使用混合含有电解液和炭黑等粒子状碳材料而成的准固体状(糊状)的电解质。其中,在含有碳材料的准固体状的电解质中,由于碳材料具有对氧化还原反应进行催化的功能,因此在电解质中也可不含卤素单质。这种氧化还原电解质还可以含有溶解上述的卤化物盐或离子性液体等的有机溶剂中的任1种或2种以上。作为该有机溶剂,可举出电化学上惰性的溶剂,例如可举出乙腈、四氢呋喃、丙腈、丁腈、甲氧基乙腈、3-甲氧基丙腈、戊腈、碳酸二甲酯、碳酸甲乙酯、碳酸亚乙酯、碳酸亚丙酯、N-甲基吡咯烷酮、戊醇、喹啉、N,N-二甲基甲酰胺、γ-丁内酯、二甲基亚砜或1,4-二噁烷等。
另外,电解质含有层30中还可以从提高光电转换元件的发电效率、提高耐久性等目的出发来添加非圆环状糖类(日本特开2005-093313号公报)、吡啶系化合物(日本特开2003-331936号公报)、尿素衍生物(日本特开2003-168493号公报)、层状粘土矿物(US2007/0275546A1)、二苄叉-D-山梨糖醇、胆固醇衍生物、氨基酸衍生物、反式-(1R,2R)-1,2-环己烷二胺的烷基酰胺衍生物、烷基尿素衍生物、N-辛基-D-葡糖酰胺苯甲酸酯、双头型氨基酸衍生物、季铵衍生物等。
该光电转换元件中,当对担载于工作电极10的色素13照射光(太阳光或与太阳光等同的紫外光、可见光或近红外光)时,吸收该光而激发的色素13将电子注入到金属氧化物半导体层12中。该电子移动至相邻的导电层11B中之后,经由外部电路到达对置电极20。另一方面,在电解质含有层30中,按照随着电子的移动被氧化的色素13返回至基底状态(进行还原)的方式将电解质氧化。该被氧化的电解质通过接收到达上述对置电极20的电子而被还原。如此,反复进行工作电极10及对置电极20之间的电子移动和伴随其的电解质含有层30中的氧化还原反应。由此,发生连续的电子移动,稳定地进行光电转换。
本发明的光电转换元件例如可如下制造。
首先,制作工作电极10。先利用电解析出法或烧成法在导电性基板11的形成有导电层11B的面上形成具有多孔质结构的金属氧化物半导体层12。利用电解析出法形成时,例如一边利用氧气或空气进行鼓泡一边使含有成为金属氧化物半导体材料的金属盐的电解浴达到规定的温度,在其中浸渍导电性基板11,在与对电极之间施加一定的电压。由此,按照具有多孔质结构的方式使金属氧化物半导体材料析出至导电层11B上。此时,还可以使对电极在电解浴中适当地运动。另外,利用烧成法形成时,例如将通过使金属氧化物半导体材料的粉末分散于分散介质中而制备的金属氧化物浆料涂布在导电性基板11上,将其干燥后进行烧成,从而使其具有多孔质结构。接着,制备在有机溶剂中溶解有包含上述通式(1)所示的本发明新型化合物的色素13的色素溶液。通过在该色素溶液中浸渍形成了金属氧化物半导体层12的导电性基板11,使色素13担载于金属氧化物半导体层12上。
上述色素溶液中的本发明的新型化合物的浓度优选为1.0×10-5~1.0×10-3mol/dm3、更优选为5.0×10-5~5.0×10-4mol/dm3。上述色素溶液中使用的有机溶剂只要是能够溶解本发明的新型化合物则无特别限定,作为具体例,可举出甲苯、苯、二甲苯等烃类;甲醇、乙醇、叔丁醇等醇类;甲基溶纤剂、乙基溶纤剂、丁基溶纤剂、二乙二醇丁醚等醚醇类;丙酮、甲乙酮、甲基异丁基酮、环己酮、双丙酮醇等酮类;乙酸乙酯、乙酸丁酯、乙酸甲氧基乙酯等酯类;丙烯酸乙酯、丙烯酸丁酯等丙烯酸酯类;2,2,3,3-四氟丙醇等氟化醇类;二氯甲烷、二氯乙烷、氯仿等氯化烃类;乙腈、四氢呋喃等,还可任意地混合这些有机溶剂。优选为甲苯、乙腈、醇类,更优选为乙腈、醇类。
接着,通过在导电性基板21的单面上形成导电层22,制作对置电极20。导电层22例如通过将导电材料进行溅射来形成。
最后,按照工作电极10的担载有色素13的面与对置电极20的形成有导电层22的面保持规定的间隔并相向的方式、介由密封剂等间隔物(未图示)进行贴合,例如将除了电解质的注入口以外的整体密封。接着,在工作电极10与对置电极20之间注入电解质之后,将注入口密封,从而形成电解质含有层30。由此,完成图1及图2所示的光电转换元件。
本发明的光电转换元件中,由于色素13包含上述通式(1)所示的本发明化合物,因此与使用了不同于本发明化合物的化合物的情况相比,可以抑制色素13从担载有色素13的载体(金属氧化物半导体层12)向电解质含有层30中溶出。这样,由于担载于金属氧化物半导体层12的色素13的量不会降低,因此从色素13向金属氧化物半导体层12的电子注入量不会降低。通过这种效果,可以提高本发明的光电转换元件的耐久性。
另外,对上述光电转换元件中在工作电极10与对置电极20之间设有电解质含有层30的情况进行了说明,但也可代替电解质含有层30而设置固体电荷移动层。此时,固体电荷移动层例如具有固体中的载流子移动影响导电的材料。作为该材料,优选电子传输材料或空穴传输材料等。
作为空穴传输材料,优选芳香族胺类或三邻亚苯衍生物类等,例如可举出低聚噻吩化合物、聚吡咯、聚乙炔或其衍生物、聚(对亚苯)或其衍生物、聚(对亚苯亚乙烯)或其衍生物、聚亚噻吩亚乙烯或其衍生物、聚噻吩或其衍生物、聚苯胺或其衍生物、聚甲苯胺或其衍生物等有机导电性高分子等。
另外,作为空穴传输材料,例如还可使用p型无机化合物半导体。该p型无机化合物半导体优选带隙为2eV以上、更优选为2.5eV以上。另外,p型无机化合物半导体的离子化电势由于是能够将色素的空穴还原的条件,因此有必要使其小于工作电极10的离子化电势。根据所使用的色素不同,p型无机化合物半导体的离子化电势的优选范围有所不同,但该离子化电势优选为4.5eV以上5.5eV以下的范围内、更优选为4.7eV以上5.3eV以下的范围内。
作为p型无机化合物半导体,例如可举出含有1价铜的化合物半导体等。作为含有1价铜的化合物半导体之一例,有CuI、CuSCN、CuInSe2、Cu(In,Ga)Se2、CuGaSe2、Cu2O、CuS、CuGaS2、CuInS2、CuAlSe2等。作为其他的p型无机化合物半导体,例如可举出GaP、NiO、CoO、FeO、Bi2O3、MoO2或Cr2O3等。
作为这种固体电荷移动层的形成方法,例如有在工作电极10上直接形成固体电荷移动层的方法,然后还可形成赋予对置电极20。
含有有机导电性高分子的空穴传输材料例如可通过真空蒸镀法、流延法、涂布法、旋涂法、浸渍法、电解聚合法或光电解聚合法等手法导入到电极内部。为无机固体化合物时,例如可通过流延法、涂布法、旋涂法、浸渍法或电镀法等手法导入到电极内部中。优选如此形成的固体电解移动层(特别是具有空穴传输材料者)的一部分为部分地渗透至金属氧化物半导体层12的多孔质结构的空隙中而发生直接接触的形态。
本发明的化合物在代替电解质含有层30而设有固体电荷移动层的光电转换元件中,与设置电解质含有层30的情况同样,也可以提高转换效率。
本发明的光电转换元件的使用用途并非限定于上述太阳能电池的用途,也可以是其他用途。作为其他的用途,例如可举出光传感器等。
实施例
以下举出本发明的新型化合物的合成例、使用了合成例中所合成的化合物的担载体(工作电极)的实施例及比较例来详细地说明本发明,但本发明并非限定于这些。
通过以下的合成例,合成上述化合物No.1~No.4、No.22、No.33~No.42。其中,作为前体的羧酸体及胺化合物为购入品或者是利用公知的方法合成的。
(合成例1)化合物No.1的合成
将MK-2Dye(Sigma-Aldrich制、0.11mmol、100mg)、二甲基甲酰胺(0.1ml)、氯仿(2ml)装入到烧瓶中,添加草酰氯(0.12mmol、15mg)搅拌1小时,之后,在0℃下添加亚氨基二乙酸二叔丁酯(0.12mmol、28mg)、二异丙基乙基胺(0.31mmol、41mg),搅拌1小时。向反应液中添加水(10ml)和氯仿(10ml)进行油水分液。利用硅胶柱色谱法(流动相;氯仿)对所得有机层进行精制,从而获得紫色固体30mg(收率为24%)。将该固体溶解在二氯甲烷(10ml)中,冷却至0℃后,添加三氟乙酸(0.08mmol、9mg)搅拌1小时。之后升温至室温,再搅拌14小时。将溶剂蒸馏除去后,利用硅胶柱色谱法(流动相为氯仿:甲醇=5:1)进行精制,从而获得红色固体14mg(收率为52%)。使用UV-VIS(λmax)、1H-NMR、IR、TOF-MS确认了所得固体为化合物No.1。将数据示于[表1]~[表4]。
(合成例2~15)化合物No.2~No.4、No.22、No.33~No.42的合成
除了使用对应于目标化合物的具有羧酸的化合物及胺化合物之外,利用与合成例1相同的手法合成了化合物No.2~No.4、No.22、No.33~No.42。将所得化合物的外观及收率示于〔表1〕。与合成例1同样地确认了所合成的化合物是目标化合物。将数据示于[表1]~[表4]。
[表1]
化合物 | 外观 | 收率% | λmax/nm | |
合成例1 | No.1 | 红色固体 | 52 | 487(CHCl3) |
合成例2 | No.2 | 红色固体 | 29 | 490(CHCl3) |
合成例3 | No.3 | 红色固体 | 40 | 495(CHCl3) |
合成例4 | No.4 | 黄色固体 | 3 | 424(CHCl3) |
合成例5 | No.22 | 紫红色固体 | 78 | 489(CHCl3) |
合成例6 | No.33 | 红褐色固体 | 58 | 476(CHCl3) |
合成例7 | No.34 | 橙色固体 | 84 | 449(CHCl3) |
合成例8 | No.35 | 紫红色固体 | 77 | 489(CHCl3) |
合成例9 | No.36 | 紫红色固体 | 99 | 500(CHCl3) |
合成例10 | No.37 | 紫红色固体 | 57 | 499(CHCl3) |
合成例11 | No.38 | 紫红色固体 | 93 | 483(CHCl3) |
合成例12 | No.39 | 紫红色固体 | 20 | 514(CHCl3) |
合成例13 | No.40 | 紫红色固体 | 63 | 512(CHCl3) |
合成例14 | No.41 | 橙色固体 | 30 | 467(CHCl3) |
合成例15 | No.42 | 橙色固体 | 32 | 427(CHCl3) |
[表2]
[表3]
[表4]
实施例 | 理论值 | m/z |
No.1 | 1069.5 | 1069.5(M+) |
No.2 | 1050.5 | 1050.6(M+) |
No.3 | 1131.5 | 1131.5(M+) |
No.4 | 571.2 | 571.2(M+) |
No.22 | 1257.6 | 1257.6(M+) |
No.33 | 737.3 | 737.4(M+) |
No.34 | 697.2 | 697.2(M+) |
No.35 | 1187.5 | 1187.4(M+) |
No.36 | 1302.6 | 1302.7(M+) |
No.37 | 1279.6 | 1279.6(M+) |
No.38 | 1185.5 | 1185.4(M+) |
No.39 | 1081.5 | 1081.4(M+) |
No.40 | 1097.4 | 1097.4(M+) |
No.41 | 621.2 | 621.4(M+) |
No.42 | 697.4 | 697.5(M+) |
使用上述合成的化合物,按照以下顺序制作本发明的担载体。
(实施例1)使用了化合物No.1的担载体(工作电极)
首先,准备由长2.0cm×宽1.5cm×厚1.1mm的导电性玻璃基板(F-SnO2)构成的导电性基板11。接着,按照围成长0.5cm×宽0.5cm的四边形的方式在导电性基板11上粘贴厚度为70μm的遮蔽胶带,在该四边形的部分上按照达到一样的厚度的方式涂布金属氧化物浆料3cm3,并将其干燥。作为金属氧化物浆料,使用按照达到10重量%的方式将氧化钛粉末(TiO2、Solaronix公司制Ti-NanoxideD)混悬于水中而成的浆料。接着,将导电性基板11上的遮蔽胶带剥离,利用电炉在450℃下对该基板进行烧成,形成厚度为约5μm的金属氧化物半导体层12。接着,将化合物No.1按照达到3×10-4mol/dm3的浓度的方式溶解在甲苯中,制备色素溶液。接着,将形成有金属氧化物半导体层12的导电性基板11浸渍于上述色素溶液中,制作了担载有色素13的工作电极10。
在以下的条件1及条件2下将所制作的工作电极10浸渍于剥离液中。
将以剥离液浸渍前的色素担载量(色素的λmax下的Abs.)为100时的剥离液浸渍后的色素担载量的比例作为耐剥离性,示于[表5]及[表6]。上述的剥离后的色素担载量的比例越接近100,则可以说耐剥离性越高。这里,色素的λmax下的Abs.如下求得:利用UV光谱仪(日立High-Technologies公司制U3010、狭缝宽度1nm)测定工作电极10的金属氧化物半导体层12的表面的吸收光谱(测定波长为300nm~800nm的范围),从而求得。
<条件1>剥离液:乙腈、浸渍条件:85℃、6小时
<条件2>剥离液:0.5M4-叔丁基吡啶乙腈:水=9:1(容量比)、浸渍条件:25℃、8小时
(实施例2~9及比较例1~2)
除了将化合物No.1替换成[表5]及[表6]的化合物以外,通过与实施例1同样的操作,制作了担载有各化合物的工作电极10,并求得色素的耐剥离性。将结果示于[表5]及[表6]。
[表5]
<条件1>
化合物 | 耐剥离性 | |
实施例1 | No.1 | 88 |
实施例2 | No.2 | 77 |
实施例3 | No.22 | 96 |
实施例4 | No.33 | 99 |
实施例5 | No.34 | 86 |
实施例6 | No.35 | 90 |
实施例7 | No.36 | 92 |
实施例8 | No.39 | 87 |
实施例9 | No.41 | 91 |
比较例1 | 比较化合物1 | 44 |
比较例2 | 比较化合物2 | 61 |
[表6]
<条件2>
化合物 | 耐剥离性 | |
实施例1 | No.1 | 93 |
实施例2 | No.2 | 80 |
实施例3 | No.22 | 99 |
实施例6 | No.35 | 81 |
实施例7 | No.36 | 91 |
实施例8 | No.39 | 79 |
比较例1 | 比较化合物1 | 52 |
比较例2 | 比较化合物2 | 60 |
如[表5]及[表6]的耐剥离性结果所示,上述通式(1)所示的本发明化合物的吸附耐久性较高。
接着,示出本发明的光电转换元件的实施例及光电转换元件的转换效率评价。
(实施例10~25及比较例3和4)
如图1所示,隔着隔离物(63μm)使使用了与上述实施例1同样制作的担载体(工作电极)的工作电极10与在作为导电性基板21的ITO电极(西野田电工株式会社制)上涂覆石墨微粒(导电层22)而制作的对置电极20相向,在它们之间配置电解质含有层30,用夹具将它们固定,使电解液〔相对于乙腈按照分别达到规定浓度的方式混合4-叔丁基吡啶(0.5mol/dm3)、碘化锂(0.5mol/dm3)、碘(0.05mol/dm3)而成的溶液〕渗透至电解质含有层30中,制作了光电转换元件。用开口部为1cm2的掩模覆盖单元电池上部,将工作电极10和对置电极20与稳压器的作用极侧及对电极侧接线,利用分光计器公司制Hyper-Monolight System SM-250进行测定,获得短路电流密度(Jsc、单位:mm/cm2)及开路电压(Voc、单位:V)。由所得的短路电流密度及开路电压的值求得光电转换元件的转换效率(%)。
将结果示于[表7]。在实施例21~25及比较例4中,作为工作电极10,使用的是代替氧化钛粉末而将氧化锌粉末(平均粒径为20nm、堺化学工业公司制FINEX-50)制成金属浆料后制作的ZnO电极。
[表7]
化合物 | 金属浆料 | 转换效率 | |
实施例10 | No.1 | TiO2 | 3.3 |
实施例11 | No.3 | TiO2 | 1.8 |
实施例12 | No.4 | TiO2 | 1.9 |
实施例13 | No.22 | TiO2 | 4.6 |
实施例14 | No.34 | TiO2 | 2.3 |
实施例15 | No.35 | TiO2 | 4.3 |
实施例16 | No.36 | TiO2 | 3.0 |
实施例17 | No.38 | TiO2 | 1.2 |
实施例18 | No.39 | TiO2 | 3.5 |
实施例19 | No.40 | TiO2 | 1.1 |
实施例20 | No.42 | TiO2 | 2.0 |
比较例3 | 比较化合物3 | TiO2 | 0.1 |
实施例21 | No.1 | ZnO | 0.9 |
实施例22 | No.2 | ZnO | 0.7 |
实施例23 | No.3 | ZnO | 0.9 |
实施例24 | No.33 | ZnO | 0.9 |
实施例25 | No.41 | ZnO | 0.8 |
比较例4 | 比较化合物1 | ZnO | 0.4 |
由上述的光电转换元件的转换效率测定结果可知,在将使用了二羧酸化合物的实施例11~21与比较例3进行比较时,通过使用本发明的具有特定结构的新型化合物,获得了高的转换效率。另外,在将实施例21~25与比较例4进行比较时可知,本发明的新型化合物显示出较高的转换效率。
由以上的结果可知,本发明的担载体的耐剥离性及耐光性优异,进而在制成光电转换元件进行使用时,显示出较高的转换效率,因此是有用的。
Claims (9)
1.一种下述通式(1)所示的新型化合物,
式中,Z为不饱和脂肪族烃基、芳香族烃基、芳香族杂环基或这些基团中的1种或2种以上连接而成的碳原子数为1~50的共轭性基团,
R1表示被羧基、氰基、氨基、酰胺基或硝基中的至少1个取代了的碳原子数为6~20的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~20的芳香族烃基或碳原子数为1~20的脂肪族烃基,该脂肪族烃基可以被-O-、-COO-、-OCO-、-NR24-、-NR24COO-或-OCONR24-中断1~3次,在中断2次以上的情况下,中断的基团不相邻;R24表示被羧基、氰基、氨基、酰胺基或硝基取代了的或未被取代的碳原子数为6~10的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~15的芳香族烃基或碳原子数为1~10的脂肪族烃基,
R2表示氢原子或可被取代的碳原子数为1~20的烃基,R30、R31、R32、R33、R40、R41、R42、R43及R44各自独立地表示氢原子或可被取代的烃基,R30与R31、R40与R41、R41与R42、R42与R43、R33与R44可分别连接形成环,
R5表示氢原子或氰基,
R11为下述部分结构式(11-1)或(11-2)所示的基团,
式中,n表示1~4的整数,
环A表示苯环、萘环、环己烷环、环己烯环或环己二烯环,
式中的除羧基的氢原子以外的氢原子可被羧基、氰基、氨基、酰胺基、硝基或者被这些基团取代了的碳原子数为1~4的脂肪族烃基或者碳原子数为1~4的无取代脂肪族烃基所取代。
2.根据权利要求1所述的新型化合物,其用下述通式(2)表示,
式中,Z、R1、R11、R2、R30、R31、R32、R40、R41、R42、R43及R5与所述通式(1)中的含义相同。
3.根据权利要求1或2所述的新型化合物,其中,Z所表示的共轭性基团为选自下述式(Z-1)~(Z-10)所示基团中的基团连接1~7个而成的基团,
式中,X表示S、O、NR6或SiR6R7,式中的除了直接键合于氮原子的氢原子之外的氢原子可以被氟原子、氯原子、碘原子、氰基、硝基、-OR6基、-SR6基、-NR6R7基、-SiR6R7R8基或可被取代的脂肪族烃基所取代,R6、R7及R8表示氢原子或可被取代的烃基。
4.根据权利要求1~3中任一项所述的新型化合物,其中,Z所表示的共轭性基团具有至少1个所述式(Z-7)所示的基团。
5.一种担载体,其担载有下述通式(1)所示的化合物,
式中,Z为不饱和脂肪族烃基、芳香族烃基、芳香族杂环基或这些基团中的1种或2种以上连接而成的碳原子数为1~50的共轭性基团,
R1表示被羧基、氰基、氨基、酰胺基或硝基中的至少1个取代了的碳原子数为6~20的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~20的芳香族烃基或碳原子数为1~20的脂肪族烃基,该脂肪族烃基可以被-O-、-COO-、-OCO-、-NR24-、-NR24COO-或-OCONR24-中断1~3次,在中断2次以上的情况下,中断的基团不相邻;R24表示被羧基、氰基、氨基、酰胺基或硝基取代了的或未被取代的碳原子数为6~10的芳香族烃基、被脂肪族烃基取代了的碳原子数为7~15的芳香族烃基或碳原子数为1~10的脂肪族烃基,
R2表示氢原子或可被取代的碳原子数为1~20的烃基,R30、R31、R32、R33、R40、R41、R42、R43及R44各自独立地表示氢原子或可被取代的烃基,R30与R31、R40与R41、R41与R42、R42与R43、R33与R44可分别连接形成环,
R5表示氢原子或氰基,
R11为下述部分结构式(11-1)或(11-2)所示的基团,
式中,n表示1~4的整数,
环A表示苯环、萘环、环己烷环、环己烯环或环己二烯环,
式中的除羧基的氢原子以外的氢原子可被羧基、氰基、氨基、酰胺基、硝基或者被这些基团取代了的碳原子数为1~4的脂肪族烃基或者碳原子数为1~4的无取代脂肪族烃基所取代。
6.根据权利要求5所述的担载体,其中,担载有下述通式(2)所示的化合物作为所述通式(1)所示的化合物,
式中,Z、R1、R11、R2、R30、R31、R32、R40、R41、R42、R43及R5与所述通式(1)中的含义相同。
7.根据权利要求5或6所述的担载体,其中,所述通式(1)中,Z所表示的共轭性基团为选自下述式(Z-1)~(Z-10)所示基团中的基团连接1~7个而成的基团,
式中,X表示S、O、NR6或SiR6R7,式中的除了直接键合于氮原子的氢原子之外的氢原子可以被氟原子、氯原子、碘原子、氰基、硝基、-OR6基、-SR6基、-NR6R7基、-SiR6R7R8基或可被取代的脂肪族烃基所取代,R6、R7及R8表示氢原子或可被取代的烃基。
8.根据权利要求5~7中任一项所述的担载体,其中,所述通式(1)中,Z所表示的共轭性基团具有至少1个所述式(Z-7)所示的基团。
9.一种光电转换元件,其具备具有权利要求5~8中任一项所述的担载体的电极。
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