CN102245711A - 含有三烷氧基甲硅烷基的新型有机染料及其制造方法 - Google Patents
含有三烷氧基甲硅烷基的新型有机染料及其制造方法 Download PDFInfo
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- CN102245711A CN102245711A CN2009801493573A CN200980149357A CN102245711A CN 102245711 A CN102245711 A CN 102245711A CN 2009801493573 A CN2009801493573 A CN 2009801493573A CN 200980149357 A CN200980149357 A CN 200980149357A CN 102245711 A CN102245711 A CN 102245711A
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- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
本发明涉及一种含有三烷氧基甲硅烷基的新型有机染料及其制造方法，本发明的染料化合物具有比以往的染料更高的光电池性能和优异的稳定性，从而用于染料敏化太阳能电池(dye-sensitized solar cell，DSSC)，能够大幅度提高电池的效率。
Description
技术领域
本发明涉及一种具有高的光电池性能和优异的稳定性而用于染料敏化太阳能电池(dye-sensitized solar cell，DSSC)、在结合团(anchoring group)含有三烷氧基甲硅烷基(trialkoxysilyl)的新型有机染料及其制造方法。
背景技术
1991年瑞士国立洛桑高等技术学院(EPFL)的迈克尔格莱才尔(MichaelGratzel)的研究小组开发了染料敏化纳米粒子氧化钛太阳能电池后，进行了很多关于该领域的研究。染料敏化太阳能电池相比于现有的硅系太阳能电池效率高，制造成本显著低，因此，具有能够代替现有的非晶质硅系太阳能电池的可能性，并且，与硅系太阳能电池不同，染料敏化太阳能电池是以能够通过吸收可见光而生成电子-空穴(hole)对的染料分子和传递所生成的电子的过渡金属氧化物作为主要组成材料的光电化学太阳能电池。
作为用于染料敏化太阳能电池的染料而广泛使用的是显示出10％以上的高光电转换效率的钌金属配位化合物，但是该钌金属配位化合物存在价格太贵并难以精制的缺点。
最近发现，在吸光效率、氧化还原反应稳定性和分子内电荷转移(charge-transfer，CT)系吸收的方面表现出优异物性的、不含有金属的有机染料可以作为能够代替昂贵的钌金属配位化合物的太阳能电池用染料来使用，所以对缺少金属的有机染料的研究正在集中进行。
有机染料一般具有通过π-键单元连接的电子给体(electron donor)-电子受体(electron acceptor)残基的结构。在大部分的有机染料中，胺衍生物起到电子给体的作用，2-氰基丙烯酸或绕丹宁残基起到电子受体的作用，这两个部位通过次甲基单元或噻吩链等π-键体系连接。
一般来说，作为电子给体的胺单元的结构变化会带来电子特性的变化，例如获得向蓝色侧位移(shift)的吸收光谱，可以通过改变π-键长度来调节吸收光谱和氧化还原电位(redox potential)。
但是，目前已知的大部分的有机染料在可见光蓝色区域具有陡而窄的吸收带，从而导致光捕获能力的减少，具有热稳定性和光稳定性比较低的缺点，因此，一直在努力开发具有高光电转换效率、且长期稳定性优异的有机染料。
发明内容
技术问题
因此，本发明的目的在于提供一种代替以往的发挥电子受体作用的2-氰基丙烯酸或绕丹宁残基、具有高光电池性能和优异的稳定性、从而能够大幅度提高太阳能电池的效率的有机染料及其制造方法。
另外，本发明的目的在于提供通过含有上述染料而表现出显著提高的光电转换效率、Jsc(短路光电流密度，short circuit photocurrent density)和摩尔吸光系数优异的染料增感光电转换元件、以及效率显著提高的太阳能电池。
技术方案
为了达到上述目的，本发明提供一种含有由下述化学式1表示的三烷氧基甲硅烷基的染料：
上述式中，
R为被C1-50的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基、芳基、烷氧基或杂芳基；
A为含有被卤素、酰胺基、氰基、羟基、硝基、酰基、C1-30的烷基、C1-30的烷氧基、C1-30的烷基羰基或C6-20的芳基取代的或者非取代的C1-50的芳基或杂芳基的2价的有机基团；
R1各自独立地为被C1-30的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基。
另外，本发明提供由上述化学式1表示的染料的制造方法，包括：(1)在有机溶剂中使下述化学式2的化合物与I2反应来制造化学式3的化合物，(2)使化学式3的化合物与由下述化学式4表示的化合物反应，
[化学式2]
R-A
[化学式3]
R-A-I
[化学式4]
SiH(OR1)3
在上述化学式2至4中，R、A、R1与化学式1中的定义相同。
另外，本发明提供一种染料增感光电转换元件，其特征在于，含有担载有由上述化学式1表示的化合物的氧化物半导体微粒。
另外，本发明提供一种染料敏化太阳能电池，其特征在于，含有上述染料增感光电转换元件。
有益效果
本发明的新型含有三烷氧基甲硅烷基的染料代替以往的发挥电子受体作用的2-氰基丙烯酸或绕丹宁残基，显示了更高的光电池性能、即更高的摩尔吸光系数、Jsc(短路光电流密度)和光电转换效率，并具有优异的稳定性，能够大幅度提高太阳能电池的效率。
附图说明
图1是对实施例1和2中制造的化学式1-1和化学式1-2的染料在各自的四氢呋喃(THF)中测定的吸光和发光光谱；
图2是使用化学式1-1和化学式1-2的染料制造的DSSC的光电池性能(单色入射光子-对-电流转换效率(IPCEs)的谱图)及光电流密度-电压(J-V)曲线(虚线：化学式1-1，实线：化学式1-2)；
图3是使用了化学式1-1和化学式1-2的染料的DSSC(为了进行比较，制造含有以往的染料N719的染料敏化太阳能电池来进行比较)的电子放出系数(a)和寿命(b)测定结果。
具体实施方式
本发明的发明人确认，将结合团(anchoring group)含有三烷氧基甲硅烷基(trialkoxysilyl)的新型染料化合物担载于氧化物半导体微粒来制造染料敏化太阳能电池时，光电转换效率、Jsc(短路光电流密度)和摩尔吸光系数高且稳定性优异，显示出高的染料敏化太阳能电池效率，从而完成了本发明。
本发明的有机染料的特征在于由下述化学式1表示。
上述式中，
R为被C1-50的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基、芳基、烷氧基或杂芳基；
A为含有被卤素、酰胺基、氰基、羟基、硝基、酰基、C1-30的烷基、C1-30的烷氧基、C1-30的烷基羰基或C6-20的芳基取代的或者非取代的C1-50的芳基或杂芳基的2价的有机基团；
R1各自独立地为被C1-30的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基。
优选地，A选自下述A-1至A-4。
上述A-1至A-4中R2和R3各自独立地为氢、卤素、酰胺基、氰基、羟基、硝基、酰基、C1-30的烷基、C1-30的烷氧基或C1-30的烷基羰基，n为1至5的整数。
优选地，R选自下述R-1至R-9。
[R-1]
(*或-部分为结合部分)
本发明的由化学式1表示的化合物更优选为由下述化学式1-1或化学式1-2表示的化合物：
另外本发明提供由上述化学式1表示的染料的制造方法，由化学式1表示的染料可以通过如下方法来制造：(1)在有机溶剂中使下述化学式2的化合物与I2反应来制造化学式3的化合物，(2)使化学式3的化合物与由下述化学式4表示的化合物反应。
[化学式2]
R-A
[化学式3]
R-A-I
[化学式4]
SiH(OR1)3
在上述化学式2至4中，R、A、R1与化学式1中的定义相同。
作为具体的一个例子，上述化学式1-1和1-2的染料可以通过如下的反应式来制造。
在上述反应式1-1和1-2中作为起始物质使用的化合物可以采用通常的方法来制造。
另外，本发明提供一种染料增感光电转换元件，所述染料增感光电转换元件的特征在于，在氧化物半导体微粒上担载有由化学式1表示的染料。本发明的染料增感光电转换元件除了使用由上述化学式1表示的染料以外，当然可以适用利用以往染料制造太阳能电池用染料增感光电转换元件的方法，优选地，本发明的染料增感光电转换元件适合利用氧化物半导体微粒在基板上制造氧化物半导体的薄膜，接着，在上述薄膜上担载本发明的染料。
在本发明中，作为设置氧化物半导体的薄膜的基板，优选其表面具有导电性的基板，还可以使用市场上销售的基板。作为具体的一个例子，可以利用在玻璃的表面、或者聚对苯二甲酸乙二醇酯或聚醚砜等具有透明性的高分子材料的表面形成涂布有铟、氟、锑的氧化锡等导电性金属氧化物或钢、银、金等金属薄膜的基板。此时，导电性一般优选为1000Ω以下，特别优选为100Ω以下。
另外，作为氧化物半导体的微粒优选金属氧化物。作为具体的例子，可以使用钛、锡、锌、钨、锆、镓、铟、钇、铌、钽、钒等的氧化物。其中，优选钛、锡、锌、铌、铟等的氧化物，其中，更优选氧化钛、氧化锌、氧化锡，最优选氧化钛。上述氧化物半导体可以单独使用，也可以混合或涂布在半导体的表面而使用。
另外，上述氧化物半导体的微粒的粒径优选以平均粒径计为1-500nm，更优选为1-100nm。另外，该氧化物半导体的微粒还可以将大粒径的和小粒径的混合，或者形成多层来利用。
上述氧化物半导体薄膜可以通过将氧化物半导体微粒用喷雾等直接在基板上形成薄膜的方法，将基板作为电极以电析出半导体微粒薄膜的方法，将半导体微粒的淤浆或含有能够通过水解半导体醇盐等半导体微粒的前体而得到的微粒的糊剂涂布在基板上后，通过干燥、固化或烧成的方法等来制造，优选将糊剂涂布在基板上的方法。在该方法的情况下，淤浆可以通过采用通常的方法将2次凝集的氧化物半导体微粒进行分散而使其在分散介质中的平均1次粒径为1-200nm来得到。
作为分散淤浆的分散介质，只要是能够分散半导体微粒的分散介质就可以没有特别的限制地使用，可以利用水、乙醇等醇、丙酮、乙酰丙酮等酮或己烷等烃，也可以将它们混合使用，其中，从减少淤浆的粘度变化的方面考虑，优选利用水。另外，以稳定氧化物半导体微粒的分散状态为目的，可以使用分散稳定剂。可以使用的分散稳定剂的具体例子可以举出醋酸、盐酸、硝酸等酸，或者乙酰丙酮、丙烯酸、聚乙二醇、聚乙烯醇等。
涂布有淤浆的基板可以进行烧成，其烧成温度为100℃以上，优选为200℃以上，另外上限大致为基材的熔点(软化点)以下，通常上限为900℃，优选为600℃以下。在本发明中，烧成时间没有特别的限定，但是优选大致为4小时以内。
在本发明中，基板上的薄膜的厚度为1-200μm比较合适，优选为1-50μm。进行烧成的情况下，虽然氧化物半导体微粒的薄层有一部分熔接，但是这样的熔接对本发明没有特别的影响。
另外，还可以对上述氧化物半导体薄膜实施2次处理。作为一个例子，还可以在与半导体相同的金属的醇盐、氯化物、氮化物、硫化物等的溶液中直接按照不同的基板沉积薄膜，并干燥或再烧成，从而提高半导体薄膜的性能。作为金属醇盐可以举出乙醇钛盐、异丙醇钛盐、叔丁醇钛盐、正二丁基二乙酰基锡等，可以利用它们的醇溶液。作为氯化物可以举出例如四氯化钛、四氯化锡、氯化锌等，可以利用其水溶液。这样获得的氧化物半导体薄膜由氧化物半导体微粒组成。
另外，在本发明中，在形成薄膜状的氧化物半导体微粒上担载染料的方法没有特别的限定，作为具体的例子可以举出以下方法：在将由上述化学式1表示的染料用能够溶解其的溶剂进行溶解而得到的溶液或将染料进行分散而得到的分散液中浸渍设置有上述氧化物半导体薄膜的基板。溶液或分散液中的浓度可以根据染料适当地决定。沉积时间大致为从常温至溶剂的沸点，另外，沉积时间是1分钟至48小时左右。作为能够用于溶解染料的溶剂的具体例子可以举出甲醇、乙醇、乙腈、二甲基亚砜、二甲基甲酰胺、丙酮、叔丁醇等。溶液的染料浓度一般为1×10-6M～1M比较合适，优选为1×10-5M～1×10-1M。这样能够得到具有被染料增感的薄膜状的氧化物半导体微粒的本发明的光电转换元件。
在本发明中担载的由上述化学式表示的染料可以为1种，也可以将数种混合。另外，在进行混合的情况下，本发明的染料可以同时与其他染料或金属配位化合物染料进行混合。能够进行混合的金属配位化合物染料的例子没有特别的限定，但是优选钌配位化合物或其季盐、酞菁、卟啉等，作为混合利用的有机染料可以举出无金属的酞菁、卟啉，或者花青苷，部花青，氧杂菁，三苯代甲烷系，WO2002/011213号公开的丙烯酸系染料等的次甲基系染料，或者呫吨系、偶氮系、蒽醌系、苝系等的染料(参照文献[M.K.Nazeeruddin，A.Kay，I.Rodicio，R.Humphry-Baker，E.Muller，P.Liska，N.Vlachopoulos，M.Gratzel，J.Am.Chem.Soc.，第115卷，6382侧(1993年)])。使用2种以上的染料的情况下，可以将染料依次吸附在半导体薄膜上，也可以混合溶解后吸附。
另外，在本发明中，在氧化物半导体微粒的薄膜上担载染料时，为了防止染料之间的结合，优选在包合物的存在下担载染料。作为上述包合物可以使用脱氧胆酸、脱氢脱氧胆酸、鹅脱氧胆酸、胆酸甲酯、胆酸钠等胆酸类，聚环氧乙烷、胆酸等类固醇系化合物，冠醚，环糊精、杯芳烃、聚环氧乙烷等。
另外，担载染料后，可以用4-叔丁基吡啶等胺化合物或醋酸、丙酸等具有酸性基团的化合物等处理半导体电极表面。处理方法可以使用例如在胺的乙醇溶液中浸泡设置有担载了染料的半导体微粒薄膜的基板的方法等。
另外，本发明提供以包括上述染料敏化光电转换元件为特征的染料敏化太阳能电池，除了使用利用了担载有由上述化学式1表示的染料的氧化物半导体微粒的染料增感光电转换元件以外，理所当然地可以适用使用以往的光电转换元件制造太阳能电池的通常的方法，作为具体的例子，可以由在上述氧化物半导体微粒上担载了由化学式1表示的染料的光电转换元件电极(阴极)、对电极(阳极)、氧化还原电解质、空穴输送材料或p型半导体等构成。
优选地，作为本发明的染料敏化太阳能电池的具体的制造方法的一个例子，可以通过以下步骤制造：在导电性透明基板上涂布氧化钛糊剂的步骤；烧成涂布有糊剂的基板而形成氧化钛薄膜的步骤；将形成有氧化钛薄膜的基板浸渍在溶解有由上述化学式1表示的染料的混合溶液中，形成吸附有染料的氧化钛膜电极的步骤；在其上部设置形成有对电极的第2玻璃基板的步骤；形成贯通第2玻璃基板和对电极的孔(hole)的步骤；在上述对电极和上述吸附有染料的氧化钛膜电极之间设置热塑性高分子膜，并实施热压工序，从而使上述对电极和氧化钛膜电极接合的步骤；通过上述孔向对电极和氧化钛膜电极之间的热塑性高分子膜注入电解质的步骤；以及用上述热塑性高分子进行密封的步骤。
氧化还原电解质、空穴输送材料、p型半导体等的形态可以是液体、凝固体(凝胶及凝胶状)、固体等。液体状的可以分别举出将氧化还原电解质、熔融盐、空穴输送材料、p型半导体等分别溶于溶剂中的或者常温熔融盐等，凝固体(凝胶及凝胶状)的情况可以分别举出使它们含在聚合物基质或低分子胶凝剂等中的等。固体的可以使用氧化还原电解质、熔融盐、空穴输送材料、p型半导体等。
作为空穴输送材料可以使用利用了胺衍生物或聚乙炔、聚苯胺、聚噻吩等导电性高分子，三亚苯系化合物等的盘状液晶相的产品。另外，作为p型半导体可以使用CuI、CuSCN等。作为对电极优选使用具有导电性、对氧化还原电解质的还原反应起到催化作用的对电极。例如，可以使用在玻璃或者高分子膜上蒸镀了铂、碳、铑、钌等，或者涂布有导电性微粒的对电极。
作为用于本发明的太阳能电池的氧化还原电解质可以使用将卤素离子作为抗衡离子的卤素化合物和卤素分子所组成的卤素氧化还原系电解质，氰亚铁酸盐-氰亚铁酸盐或二茂铁-二茂铁离子、钴配位化合物等金属配位化合物等的金属氧化还原系电解质、烷基硫醇-烷基二硫化物、紫罗碱染料、氢醌-醌等有机氧化还原系电解质等，优选卤素氧化还原系电解质。作为由卤素化合物-卤素分子组成的卤素氧化还原系电解质中的卤素分子优选碘分子。另外，作为将卤素离子作为抗衡离子的卤素化合物可以使用LiI、NaI、KI、CaI2、MgI2、CuI等卤化金属盐，或者四烷基碘化铵、咪唑
碘、吡啶碘等卤素的有机铵盐，或者I2。
另外，氧化还原电解质由包含它的溶液的形态存在时，该溶剂可以使用电化学上具有惰性的溶剂。作为具体例子可以举出乙腈、碳酸亚丙酯、碳酸亚乙酯、3-甲氧基丙腈、甲氧基乙腈、乙二醇、丙二醇、一缩二乙二醇、二缩三乙二醇、丁内酯、二甲氧基乙烷、碳酸二甲酯、1，3-二氧戊环、甲酸甲酯、2-甲基四氢呋喃、3-甲氧基-唑烷-2-酮、环丁砜、四氢呋喃、水等，特别优选乙腈、碳酸亚丙酯、碳酸亚乙酯、3-甲氧基丙腈、乙二醇、3-甲氧基-
唑烷-2-酮、丁内酯等。上述溶剂可以使用1种或者混合使用。
在凝胶状的阳电解质的情况下，可以使用在低聚物、聚合物等的基质中含有电解质或电解质溶液的阳电解质，或者在低分子胶凝剂等中同样含有电解质或电解质溶液的阳电解质。氧化还原电解质的浓度优选为0.01-99重量％，更优选0.1-30重量％。
本发明的太阳能电池可以通过以下方法得到：在基板上的氧化物半导体微粒上担载有染料的光电转换元件(阴极)上，与其对置地配置对电极(阳极)，并在它们之间填充含有氧化还原电解质的溶液。
以下，为了助于理解本发明，提供优选实施例，但下述实施例仅例示本发明，本发明的范围并不限定于下述实施例。
实施例
实施例1化合物1-1的合成
根据反应式1-1的记载制造了化合物1-1。
实施例2化合物1-2的合成
根据反应式1-2的记载制造了化合物1-1。
实施例3染料敏化太阳能电池的制造
为了评价根据本发明的染料化合物的电流-电压特性，利用10+4μm TiO2双层制造太阳能电池。将TiO2糊剂(Solaronix，Ti-Nanoxide T/SP)在掺氟二氧化锡(FTO)玻璃基板上进行丝网印刷，制造10μm厚度的第一TiO2透明层，为了光散射，另外用糊剂(CCIC，PST-400C)制造4μm厚度的第二TiO2散射层。将该TiO2电极在70℃下用40mM TiCl4溶液处理30分钟，在500℃下烧结30分钟。
接着，将该TiO2电极分别浸渍到上述实施例1和2中制造的本发明的染料化合物1-1溶液和化合物1-2溶液(四氢呋喃中含有0.3mM染料)中后，在常温下放置24小时。在吸附有染料的TiO2电极和铂-对电极之间放置作为隔片的高温熔融膜(Surlyn)，以80℃进行加热，从而装配了密封的夹层结构电池。作为电解质溶液，使用了在3-甲氧基丙腈(MPN)中溶解有1，2-二甲基-正丙基碘化咪唑
(DMPImI)(0.6M)、I2(0.1M)、NMBI(0.5M)和聚偏氟乙烯-六氟丙烯共聚物(PVDF-HFP)(5重量％)的溶液。
试验例实施例中制造的染料以及包含该染料的染料敏化太阳能电池的物性测定
测定上述实施例1和2中制造的有机染料的物性并表示在图1中，测定含有上述有机染料的染料敏化太阳能电池的物性并表示在图2至3中，并将其结果整理在下表1来表示。
表1
将实施例1和2中制造的化学式1-1和1-2的染料在四氢呋喃(THF)中测定的吸光和发光光谱表示在图1中。(灰色：化学式1-1，黑色：化学式1-2)化学式1-1的吸光光谱在374nm和402nm中显示2个最大吸光峰，化学式1-2的情况是在373nm和419nm显示最大吸光峰。像这样，与化学式1-1的染料相比，化学式1-2的染料能够将光的吸收带更向长波长移动。
另外，将上述化学式1-1和1-2的染料的光电池性能(单色入射光子-对-电流转换效率(IPCEs)的谱图)及光电流密度-电压(J-V)曲线表示在图2中。(虚线：化学式1-1，实线：化学式1-2)
另外，测定担载化学式1-1和1-2而制造的DSSC(为了进行比较，制造含有以往的染料N719的染料敏化太阳能电池来进行比较)的电子放出系数(a)和寿命(b)，表示在图3中。(白点：化学式1-1，黑点：化学式1-2)
由上述图1至3和表1中记载的多种结果可知，本发明的新型染料显示出了优异的摩尔吸光系数、Jsc(短路光电流密度)、光电转换效率和稳定性，从而可作为染料敏化太阳能电池的染料来良好地使用。
产业上的利用可能性
本发明的新型含有三烷氧基甲硅烷基的染料代替以往的发挥电子受体作用的2-氰基丙烯酸或绕丹宁残基，显示了更高的光电池性能、即更高的摩尔吸光系数、Jsc(短路光电流密度)和光电转换效率，并具有优异的稳定性，能够大幅度提高太阳能电池的效率。
Claims (9)
1.一种含有三烷氧基甲硅烷基的染料，其特征在于，所述三烷氧基甲硅烷基由下述化学式1表示，
所述式中，
R为被C1-50的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基、芳基、烷氧基或杂芳基；
A为含有被卤素、酰胺基、氰基、羟基、硝基、酰基、C1-30的烷基、C1-30的烷氧基、C1-30的烷基羰基或C6-20的芳基取代的或者非取代的C1-50的芳基或杂芳基的2价的有机基团；
R1各自独立地为被C1-30的烷基、烷氧基、卤素、酰胺基、氰基、羟基、硝基、酰基、芳基或杂芳基取代的或者非取代的C1-50的烷基。
2.根据权利要求1所述的含有三烷氧基甲硅烷基的染料，其中，所述A选自由下述A-1至A-4组成的组，
所述A-1至A-4中R2和R3各自独立地为氢、卤素、酰胺基、氰基、羟基、硝基、酰基、C1-30的烷基、C1-30的烷氧基或C1-30的烷基羰基，n为1至5的整数。
3.根据权利要求1所述的含有三烷氧基甲硅烷基的染料，其中，所述R选自由R-1至R-9组成的组，
R-1
*或-部分为结合部分。
4.根据权利要求1所述的含有三烷氧基甲硅烷基的染料，其中，所述染料是由下述化学式1-1或化学式1-2表示的化合物：
5.一种含有由化学式1表示的三烷氧基甲硅烷基的染料的制造方法，其特征在于，包括：(1)在有机溶剂中使下述化学式2的化合物与I2反应来制造化学式3的化合物，(2)使化学式3的化合物与由下述化学式4表示的化合物反应，
化学式2
R-A
化学式3
R-A-I
化学式4
SiH(OR1)3
在所述化学式2至4中，R、A、R1与所述权利要求1的化学式1中的定义相同。
6.根据权利要求5所述的含有由化学式1表示的三烷氧基甲硅烷基的染料的制造方法，其中，所述染料的制造方法根据下述反应式1-1或1-2进行，
7.一种染料增感光电转换元件，其特征在于，含有担载有权利要求1所述的含有三烷氧基甲硅烷基的染料的氧化物半导体微粒。
8.一种染料敏化太阳能电池，其特征在于，含有权利要求7所述的染料增感光电转换元件作为电极。
9.根据权利要求8所述的染料敏化太阳能电池，其中，所述染料敏化太阳能电池通过以下步骤制造：在导电性透明基板上涂布氧化钛糊剂的步骤；将涂布有糊剂的基板进行烧成而形成氧化钛薄膜的步骤；将形成有氧化钛薄膜的基板浸渍在溶解有由化学式1表示的染料的混合溶液中，形成吸附有染料的氧化钛膜电极的步骤；在其上部设置形成有对电极的第2玻璃基板的步骤；形成贯通第2玻璃基板和对电极的孔的步骤；在所述对电极和所述吸附有染料的氧化钛膜电极之间设置热塑性高分子膜，并实施热压工序，从而使所述对电极和氧化钛膜电极接合的步骤；通过所述孔向对电极和氧化钛膜电极之间的热塑性高分子膜注入电解质的步骤；以及用所述热塑性高分子进行密封的步骤。
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| KR10-2008-0124833 | 2008-12-09 | ||
| PCT/KR2009/007267 WO2010067996A2 (ko) | 2008-12-09 | 2009-12-07 | 트리알콕시실릴기 함유 신규 유기염료 및 이의 제조방법 |
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| CN103415527B (zh) | 2011-04-05 | 2016-06-29 | 株式会社艾迪科 | 化合物以及光电转换元件 |
| EP2873662A1 (en) | 2013-11-15 | 2015-05-20 | Heraeus Precious Metals GmbH & Co. KG | Star-shaped compounds for dye-sensitized solar cells |
| WO2023190987A1 (ja) * | 2022-03-31 | 2023-10-05 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0140620A1 (en) * | 1983-10-11 | 1985-05-08 | Montedison S.p.A. | Silane anthraquinone dyes, composite pigments obtainable therefrom, and processes for preparing the same |
| CN1989142A (zh) * | 2004-07-21 | 2007-06-27 | 夏普株式会社 | π电子共轭的有机硅烷化合物及其合成方法 |
| WO2008147070A2 (en) * | 2007-05-28 | 2008-12-04 | Dongjin Semichem Co., Ltd. | Novel organic dye and method of preparing the same |
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| CA2417502C (en) | 2000-07-27 | 2012-01-10 | Nippon Kayaku Kabushiki Kaisha | Dye-sensitized photoelectric conversion device |
| US20090005557A1 (en) * | 2004-07-21 | 2009-01-01 | Masatoshi Nakagawa | Electron-Conjugated Organic Silane Compound and Production Method Thereof |
| KR20070017058A (ko) * | 2005-08-04 | 2007-02-08 | 제너럴 일렉트릭 캄파니 | 유기 염료 조성물 및 광기전력 전지에서의 이의 용도 |
| CN101283052A (zh) * | 2005-10-12 | 2008-10-08 | 西巴特殊化学品控股有限公司 | 封装的发光颜料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0140620A1 (en) * | 1983-10-11 | 1985-05-08 | Montedison S.p.A. | Silane anthraquinone dyes, composite pigments obtainable therefrom, and processes for preparing the same |
| CN1989142A (zh) * | 2004-07-21 | 2007-06-27 | 夏普株式会社 | π电子共轭的有机硅烷化合物及其合成方法 |
| WO2008147070A2 (en) * | 2007-05-28 | 2008-12-04 | Dongjin Semichem Co., Ltd. | Novel organic dye and method of preparing the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103918050A (zh) * | 2011-12-28 | 2014-07-09 | 株式会社艾迪科 | 色素敏化太阳能电池 |
| CN103918050B (zh) * | 2011-12-28 | 2016-12-07 | 株式会社艾迪科 | 色素敏化太阳能电池 |
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| KR20100066158A (ko) | 2010-06-17 |
| WO2010067996A2 (ko) | 2010-06-17 |
| TW201030102A (en) | 2010-08-16 |
| WO2010067996A3 (ko) | 2010-09-30 |
| EP2386607A4 (en) | 2012-08-08 |
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