CN1685031A - 导电有机聚合物/纳米微粒组合物及其应用方法 - Google Patents

导电有机聚合物/纳米微粒组合物及其应用方法 Download PDF

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CN1685031A
CN1685031A CNA038225239A CN03822523A CN1685031A CN 1685031 A CN1685031 A CN 1685031A CN A038225239 A CNA038225239 A CN A038225239A CN 03822523 A CN03822523 A CN 03822523A CN 1685031 A CN1685031 A CN 1685031A
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Abstract

提供了包含导电有机聚合物和许多纳米微粒组成的水分散体的组合物。用本发明组合物铸塑而成的膜可用作电致发光器件中的缓冲层，如有机发光二极管(OLED)和薄膜场效应晶体管的电极。含有纳米微粒的缓冲层的电导率比不含纳米微粒的缓冲层的电导率低得多。此外，本发明缓冲层嵌入电致发光(EL)器件后，它能提高EL器件的应力寿命。

Description

导电有机聚合物/纳米微粒组合物及其应用方法
发明领域
本发明涉及导电有机聚合物在像素化电致发光器件生产中的应用，所述器件如有机发光二极管和薄膜场效应晶体管电极。
发明背景
导电有机聚合物早在20多年前就引起研究者的注意。这些聚合物之所以比传统导电材料(例如金属、半导体金属氧化物)更能引起人的兴趣，主要是起因于这些因素，如重量轻、弹性、耐用性且容易加工。目前，商业上最为成功的导电有机聚合物是聚苯胺和聚噻吩，市场上有许多商品名。这些材料可在水溶性聚酸，如聚(苯乙烯磺酸)(PSS)存在下，通过苯胺或二氧噻吩单体在水溶液的聚合反应制备，如美国专利5300575“Polythiophene dispersions，theirproduction and their use”所述。用于发光显示器的电致发光(EL)器件和用作电极的薄膜场效应晶体管的最新进展催生了导电有机聚合物的新领域。EL器件，如含有导电有机聚合物的有机发光二极管(OLED)通常具有如下结构：
                  阳极/缓冲层/EL聚合物/阴极阳极通常是任何能够在半导电性EL聚合物充满的π键中注入空穴的材料，例如氧化铟/锡(ITO)。阳极可任选支撑在玻璃或塑料基材上。EL聚合物通常是共轭半导电性有机聚合物，如聚(对亚苯基亚乙烯基)或聚芴。阴极通常是任何能够在半导电性E聚合物的空π*键中注入电子的材料，如Ca或Ba。
缓冲层通常是导电有机聚合物，它能够可帮助空穴从阳极注入EL聚合物层。缓冲层也可称作空穴注射层、空穴输送层，也可以作为双层阳极的一部分。用作缓冲层的典型水分散性导电有机聚合物有聚苯胺(PAni)的翠绿亚胺盐或掺有聚磺酸的聚二氧亚烷基噻吩。
虽然为了帮助电荷转移，缓冲层必须具有一定的导电性，但由常见的聚苯胺或聚噻酚水分散体形成的缓冲层膜的最高电导率一般为10-3S/cm左右。所述电导率通常大约比需要的高3个数量级。实际上，为防止阳极线(或像素)之间串扰，缓冲层的电导率应当减小到大约10-6S/cm，但不能对含有这种缓冲层的器件的发光性质造成不良影响。例如，用市售聚(亚乙基二氧噻吩)水分散体(Baytron-P VP A1 4083，H.C.Starck，GmbH，Leverkusen，Germany生产)制备的膜，其电导率约为10-3S/cm。要防止像素之间串扰，这个值还太高。因此，需要可用于电致发光器件的高电阻缓冲层。
发明概述
提供了包含导电有机聚合物和许多纳米微粒的水分散体的组合物。本发明组合物能够提供连续光滑薄膜，作为电致发光器件的缓冲层，如有机发光二极管(OLED)或薄膜场效应晶体管的电极。可用于本发明的纳米微粒可以是无机或有机微粒。包含无机或有机纳米微粒的缓冲层比不含这种纳米微粒的缓冲层所具有的电导率低得多。装入电致发光(EL)器件后，本发明的缓冲层提供了高电阻，同时可提高EL器件的应力寿命。
本发明的另一种实施方式提供了包含用本发明水分散体铸塑的缓冲层的电致发光器件。
本发明的另一种实施方式提供了降低导电有机聚合物膜的电导率的方法，所述导电聚合物膜通过在基底上铸塑导电聚合物的水分散体形成，该方法包括在水分散体中加入许多纳米微粒。
本发明的另一种实施方式提供了制备厚度更大的缓冲层的方法，所述方法包括在导电有机聚合物的水分散体中加入许多纳米微粒，并将所述水分散体铸塑到基底上，形成缓冲层。
本发明的另一种实施方式提供了薄膜场效应晶体管电极，所述电极由本发明的水分散体铸塑而成。
本发明的另一种实施方式提供了提高薄膜场效应晶体管电极的电导率的方法，所述电极用本发明的水分散体在基底上铸塑而成。
附图简述
图1所示为含有本发明缓冲层的电子器件的截面图。
图2所示为含有本发明电极的薄膜场效应晶体管的截面图。
发明详述
提供了包含导电有机聚合物和许多纳米微粒的水分散体的组合物。这里所用术语“分散体”是指含有微粒悬浮物的连续介质。本发明中的“连续介质”通常是水性液体，例如水。本发明的纳米微粒可以是无机微粒或有机微粒。这里所用术语“无机微粒”是指基本上不含碳的纳米微粒，而“有机微粒”是指基本上由碳组成的纳米微粒。这里所用术语“纳米微粒”是指粒度小于1000纳米(nm)的微粒。
本发明的组合物通常包含连续水相，其中分散有导电有机聚合物。举例来说，可用于本发明的导电有机聚合物包括各种形式的聚苯胺(例如无色翠绿亚胺、翠绿亚胺、苯胺黑等)，它们能够形成酸/碱盐，提供聚合物导电性。众所周知，根据氧化程度不同，可以合成不同形式的聚苯胺聚合物。聚苯胺(PAni)一般可以说由含有下式I所示芳胺氮原子和/或下式II所示芳亚胺氮原子的单体单元组成：
其中，n是0-4之间的整数，
R独立选择，它在每个单元中可相同或不同，选自烷基、烯基、烷氧基、环烷基、环烯基、烷酰基、烷硫基、芳氧基、烷基硫代烷基、烷基芳基、芳烷基、氨基、烷氨基、二烷基氨基、芳基、烷基亚硫酰基、烷氧基烷基、烷基硫酰基、芳硫基、芳基亚硫酰基、烷氧基羰基、芳基硫酰基、羧酸、卤素、氰基，或含有一个或多个磺酸、羧酸、卤素、硝基、氰基或环氧取代基的烷基；或者任何两个R基可一起构成亚烷基或亚烯基链，该链围成3、4、5、6或7元芳环或脂环，该环可任选包含一个或多个二价氮、硫或氧原子。
尽管化学式I和II示出的单体单元是非质子化的，但众所周知，在酸(例如聚(2-丙烯酰氨基-2-甲基-1-丙烷磺酸)(PAAMPSA)、聚(苯乙烯磺酸)(PSS)等)存在下，碱性氮原子将通过质子化形成盐。亚胺氮原子与胺氮原子的相对比例以这样形式增加，具有化学式I的单体单元和具有化学式II的单体单元的比例是2∶1。在此实施方式中，胺氮原子与亚胺氮原子的比例是1∶1。
在另一种实施方式中，导电有机聚合物是聚(二氧噻吩)。用于本发明的聚(二氧噻吩)具有下式III：
其中：
R1和R1’各自独立选自氢和含有1-4个碳原子的烷基，
或者R1和R1’一起形成含有1-4个碳原子的亚烷基链，可任选为含有1-12个碳原子的烷基或芳基或1，2-环亚己基所取代，
n约大于9。
用于本发明组合物和方法的导电有机聚合物一般通过在含有聚酸(例如PAMMPSA、PSS等)水溶液中相应单体的氧化聚合反应制备。氧化聚合反应用过硫酸铵、过硫酸钠等氧化剂进行。因此，举例来说，当苯胺在PAAMPSA存在下发生氧化聚合时，形成导电的酸/碱盐PAni/PAAMPSA。当亚乙基二氧噻吩(EDT)在PSS存在下发生氧化聚合时，形成导电的酸/碱盐聚(亚乙基二氧噻吩)(PEDT)/PSS。
水溶液还可包含聚合反应催化剂，如硫酸铁、氯化铁等。聚合反应通常在低温下进行，例如在-10℃至30℃之间。聚合反应完成后，可任选用对所得聚合物的非溶剂，例如丙酮等将聚合物从水分散体中沉淀出来，由此分离聚合物。导电有机聚合物分离后，可对该材料进行精炼，得到粒度约小于1000nm的聚合物微粒。在一种实施方式中，聚合物微粒的粒度约小于500nm。在另一种实施方式中，聚合物微粒约小于50nm。接着，将分离出来的导电有机聚合物微粒要么直接与纳米微粒水分散体直接合并，要么先重新分散在水中，然后再与纳米微粒的水分散体合并。
在本发明方法的另一种实施方式中，氧化聚合反应在纳米微粒存在下进行，由此产生水分散体，而无需分离导电有机聚合物。例如，可在含苯胺单体的水溶液中加入纳米微粒，从而形成分散体。接着可加入氧化剂，使单体在纳米微粒存在下发生聚合。本发明的此实施方式从经济角度看非常有吸引力，因为它通过“单锅”合成形成了本发明的水分散体。用上述任意一种方法制备的本发明水分散体具有这样一个优点，它容易过滤(例如)通过Millex 0.45μm HV滤器。因此，本发明水分散体很容易形成连续光滑膜。
在发生氧化聚合反应之前，可任选在水溶液中加入有机添加剂，如位阻稳定剂。这些添加剂有助于形成含有纳米微粒的导电有机聚合物。举例来说，有机添加剂包括聚丙烯酰胺、聚乙烯醇、聚(2-乙烯基吡啶)、聚(乙酸乙烯酯)、聚(乙烯甲基醚)、聚(乙烯吡咯烷酮)、聚(乙烯丁缩醛)等。
用于本发明的纳米微粒可以是无机微粒或有机微粒。用于本发明的无机纳米微粒包括氧化铝、氧化硅、金属纳米微粒、半导性金属氧化物等。在一种实施方式中，半导电性金属氧化物可选自混合价金属氧化物，如锑酸锌等。在另一种实施方式中，金属纳米微粒是纳米钼。用于本发明的有机纳米微粒包括胶体磺酸(如全氟亚乙基磺酸酯等)、聚丙烯酸酯、聚磷酸酯、碳纳米管等。
用于本发明的纳米微粒可具有各种形状和尺寸。在一种实施方式中，纳米微粒基本上是球形的。在另一种实施方式中，纳米微粒基本上是长形的，如金属纳米线。用于本发明的纳米微粒的平均粒径通常约小于500nm。在另一种实施方式中，纳米微粒的平均粒径约小于100nm。在另一种实施方式中，纳米微粒的平均粒径约小于50nm。在另一种实施方式中，长形纳米微粒的长径比大于1-100。长径比定义为微粒宽度与微粒长度之比。对于长形微粒，“粒径”是指微粒宽度。在另一种实施方式中，纳米微粒具有不规则几何形状。对于形状不规则的微粒，“粒度”是指微粒能通过的最小网孔的尺寸。本发明的另一种实施方式提供了由含有导电有机聚合物和纳米微粒的水分散体铸塑而成的缓冲层。导电聚合物和纳米微粒均易分散于水中。因此，可通过铸塑含有导电聚合物和纳米微粒的水分散体来制备连续光滑膜。与组成相同但不含无机纳米微粒的缓冲层相比，本发明缓冲层的电导率下降了。电阻率与电导率成反比。因此，这里所用词汇“高电阻”与“低电导”用来描述缓冲层时，可以互换使用。这里所用词汇“高电阻”和“低电导”各自指电导率小于市售缓冲层的电导，即约小于1.0×10-3S/cm。在另一种实施方式中，电导率宜小于1.0×10-5S/cm。电阻率和电导率的值一般分别以欧姆-厘米(Ω-cm)和西门子/厘米(S/cm)报道。这里一般报告电导率值(以S/cm为单位)，而不报告电阻率值。
本发明的另一种实施方式提供了两个电接触层之间含有至少一个电致发光层(通常为半导体共轭聚合物)的电子器件，其中器件的至少一个层包含本发明的缓冲层。如图1所示，典型的器件包含阳极层110、缓冲层120、电致发光层130和阴极层150。靠近阴极层150的是任选电子注射/输送层140。在缓冲层120和阴极层150(或任选电子注射/输送层140)之间是电致发光层130。
所述器件包含靠近阳极层110或阴极层150的载体或基底(未示出)。载体多数情况下靠近阳极层110。载体可以是弹性的或刚性的，可以是有机的或无机的。一般，玻璃或弹性有机膜可以用作载体。阳极层110是比阴极层150更有效注射空穴的电极。阳极可以包含含有金属、混合金属、合金、金属氧化物或混合氧化物的材料。合适的材料包括第2族元素(即Be、Mg、Ca、Sr、Ba、Ra)、第11族元素、第4～6族元素和第8～10族过渡元素的混合氧化物。如果阳极层110需要发光，则可用第12～14族元素的混合氧化物，如氧化锡铟。这里所用词汇“混合氧化物”是指含有两种或多种不同阳离子的氧化物，所述阳离子选自第2族元素或第12、13或14族元素。用于阳极层110的材料的某些非限制性具体实例包括氧化锡铟(ITO)、氧化锡铝、金、银、铜和镍。阳极还可包含有机材料，如聚苯胺或聚噻吩。
阳极层110可通过化学或物理沉积工艺或旋铸工艺形成。化学气相沉积可以等离子体促进化学气相沉积(PECVD)或金属有机化学气相沉积(MOCVD)的形式进行。物理气相沉积包括所有形式的溅射(包括离子束溅射)以及电子束蒸镀和电阻蒸镀。物理气相沉积的具体形式包括RF磁电管溅射和感应—耦合等离子体物理气相沉积(IMP-PVD)。这些沉积技术在半导体制造领域是广为人知的。
阳极层110通常在平版印刷操作中成图。所成图案可根据需要变化。阳极层可以这样形成图案，例如，施加第一电接触层材料之前，在第一弹性复合屏蔽结构上放置成图掩模或蚀刻剂。或者，阳极层也可以用作整体层(亦称掩蔽沉积层)，然后用如成图蚀刻剂层和湿化学或干蚀刻技术等形成图案。也可以采用本领域熟知的其他成图工艺。如果电子器件排布成列，则阳极层110一般形成基本上平行的条，它们的长度向基本上相同的方向延伸。
缓冲层120通常用本领域技术人员熟悉的各种技术铸塑到基底上。举例来说，常用的铸塑技术包括溶液铸塑、滴铸、幕涂铸塑、旋涂、丝网印刷、喷墨打印等。或者，缓冲层可以用这些技术，如喷墨打印技术成图。
电致发光(EL)层130通常是共轭聚合物，如聚(对亚苯基亚乙烯基)或聚芴。具体材料可根据具体应用、运行时所用电压或其他因素进行选择。含有电致发光有机材料的EL层130可用任何常规技术，包括旋涂、铸塑和印刷技术从溶液中施涂。EL有机材料可用气相沉积工艺直接施用，具体取决于材料的性质。在另一种实施方式中，可施用EL聚合物前体，然后将其转化为聚合物，通常要用到热量或其他外部能源(例如可见光或UV辐射)。
任选层140同时具有两个作用，一个是帮助电子注射/输送，另一个是作为约束层，防止猝灭层界面上的反应。更具体地说，层140可促进电子迁移，减少层130和150直接接触时发生猝灭反应的可能。用于任选层140的材料的例子包括金属螯合的oxinoid化合物(例如Alq3等)；菲洛啉基化合物(例如2，9-二甲基-4，7-二苯基-1，10-菲洛啉)(DDPA)，4，7-二苯基-1，10-菲洛啉(DPA)等)；唑类化合物(例如2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(PBD等)，3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑(TAZ等))；其他类似化合物；或者它们中的任何一种或多种组合。或者，任选层140可以是无机层，包含BaO、LiF、Li2O等。
阴极层150是能够特别有效地注射电子或负电荷载体的电极。阴极层150可以是功函小于第一电接触层(在这里是阳极层110)的任何金属或非金属。这里所用术语“功函较小”是指该材料的功函不大于约4.4eV。这里所用“功函较高”是指该材料的功函至少约4.4eV。
用于阴极层的材料可选自第1族的碱金属(例如Li、Na、K、Rb、Cs)、第2族金属(例如Mg、Ca、Ba等)、第12族金属、镧系元素(例如Ce、Sm、Eu等)和锕系元素(例如Th、U等)。也可以用铝、铟、铱等材料，包括它们的组合。用于阴极层150的材料的具体但非限制性例子包括钡、锂、铈、铯、铕、铷、钇、镁和钐。
阴极层150通常用化学或物理气相沉积工艺形成。一般地，阴极层可按照上面讨论阳极层110时所用方法成图。如果电子器件排布成列，则阴极层150可形成基本上平行的条，它们的长度方向基本上朝向同一个方向，且基本上垂直于阳极层条的长度方向。称作像素的电子元件形成于交叉点(平视或俯视时，阳极层条与阴极层条交叉的位置)。
在其他实施方式中，有机电子器件中还可存在其他层。例如，缓冲层120和EL层130之间的层(未示出)可促进正电荷的输送、层间带隙匹配，作为保护层等。类似地，EL层130与阴极层150之间的其他层(未示出)可促进负电荷输送、层间带隙匹配，作为保护层等。可以采用本领域熟知的层。此外，任何上述层可由两个或多个层制备。或者，可对无机阳极层110、缓冲层120、EL层130和阴极层150中的某些或全部层进行表面处理，以提高电化载体的输送效率。每个组分层所用材料的选择可在均衡考虑所生产器件的效率、生产成本、生产工艺的复杂程度或其他可能因素之后决定。
根据电子器件的目标用途，EL层130可以是受信号激发的发光层(例如在发光二极管中)，或者响应辐射能并发出信号的材料层，可以施加电压或不施加电压(如检测器或伏打电池)。对辐射能有响应的电子器件的例子可选自光导电池、光电导管、光控开关、光电晶体管和光电管，以及光伏打电池。阅读本说明书后，有经验的技术人员将能够选择适合特定应用的材料。发光材料可分散在另一种材料的基体中，可以加入添加剂，也可不加添加剂，但宜单独形成层。EL层130的厚度通常约在50-500nm之间。
在有机发光二极管(OLED)中，分别从阴极层150和阳极层110注入到EL层130的电子和空穴，在聚合物中形成带负电和带正电的极化子。这些极化子在外加电场作用下发生迁移，形成带有相反电荷的极化激发子，然后进行辐射复合。对器件阳极和阴极之间施加足够的电势差，通常约小于12伏，在许多情况下不大于约5伏。实际电势差取决于器件在较大电子组件中的应用。在许多实施方式中，阳极层110在电子器件的操作中偏置到正电压，而阴极层150基本上为接地电势或0电势。电池或其他电源可电连接到电子器件上，作为电路的一部分，但在图1中没有示出。
本发明还提供了薄膜场效应晶体管电极。在薄膜场效应晶体管中，介电聚合物或介电氧化物薄膜在一面配有栅极，而另一面配有源极。在漏极和源极之间沉积有机半导体膜。有机半导电聚合物膜一般用芳香溶剂如甲苯，或氯化有机溶剂如氯仿从有机溶液中铸塑而成。为适合电极应用，导电聚合物和用来分散或溶解导电聚合物的液体必须与半导电聚合物和半导电聚合物用的溶剂相容，以避免导电聚合物或半导电聚合物的再溶解。用导电聚合物制备的薄膜场效应晶体管电极的电导率大于10S/cm。但是，只用聚合酸制备的导电聚合物的电导率约为～10-3S/cm或更低。为提高导电聚合物的电导率，同时又不会损害其可加工性(如铸塑、旋涂等)，需要强导电添加剂。因此，本发明的另一种实施方式提供了薄膜场效应晶体管电极。本发明电极从含有导电聚合物和纳米微粒的水分散体铸塑而成。在此实施方式中，纳米微粒通常是碳纳米管、金属纳米微粒或金属纳米线，所得电极的电导率约大于10S/cm。在另一种实施方式中，导电聚合物是聚苯胺/聚合酸，聚二氧亚烷基噻吩/聚合酸等。
本发明还提供了含有本发明电极的薄膜场效应晶体管。图2所示薄膜场效应晶体管通常按以下方法制备。介电聚合物或介电氧化物薄膜210的一面有栅极220，而另一面分别有漏极和源极230和240。漏极和源极之间沉积了有机半导电膜250。本发明含有纳米线或碳纳米管的水分散体在栅极、漏极和源极上可得到理想的应用，因为它们与溶液薄膜沉积中的有机介电聚合物和半导电聚合物相容。
本发明的另一种实施方式提供了降低从水分散体铸塑在基底上的导电有机聚合物膜电导率的方法，使电导率小于约1×10-5S/cm。举例来说，这种方法可通过在导电聚合物的水分散体中加入许多纳米微粒来进行。令人意外的发现是，即使在这里所述导电有机聚合物膜中加入半导电无机纳米微粒，也能降低聚合物膜的电导率。在一种实施方式中，导电有机聚合物膜可用作电致发光器件的缓冲层。在另一种实施方式中，导电聚合物膜是PAni/PAAMPSA。
本发明的另一种实施方式提供了制造更厚缓冲层的方法。举例来说，这种方法可这样进行，即在导电有机聚合物的水分散体中加入许多纳米微粒，然后将所述水分散体铸塑到基底上，形成缓冲层。在导电聚合物的水分散体中加入纳米微粒后，得到的水分散体的粘度提高。提高粘度后，可更好地控制由水溶液铸塑而成的层的厚度。控制缓冲层的厚度是有利的，因为功能正常的缓冲层的合适厚度在一定程度上取决于沉积缓冲层的金属导电层的表面粗糙度。
下面将结合以下非限制性实施例对本发明进行更详细的介绍。
实施例
比较例1
此比较例说明了PAni/PAAMPSA的制备，及其作为缓冲层的电导率和发光器件性质。
按以下方法合成。将苯胺(4.08g)溶解在150ml含有PAAMPSA(6.35g，购自Sigma-Aldrich Corp.，St.Louis，MO，USA的PAAMPSA)的水溶液中，形成15wt％水溶液；PAAMPSA的重均分子量是2,000,000。将含有苯胺和PAAMPSA的水溶液装入500ml四颈圆底烧瓶中，用冰/水浴冷却到约4℃。用磁力搅拌器连续搅拌溶液。在冷却的苯胺/PAAMPSA水溶液中，以恒定速率在1小时时间内加入100ml含有4.235g PAAMPSA和2.36g过硫酸铵的水溶液。聚合反应进行198分钟。
然后将反应混合物倒入两个离心瓶中，在15℃下以8000rpm的速度离心30分钟。离心之后，将上清液缓慢倒入丙酮，沉淀出聚合物产物。沉淀之后，用丙酮反复冲洗固体聚合物，过滤，在真空炉(约18Hg.，通N2，室温)中干燥过夜，产量为7.03g。
将上面制备的PAni/PAAMPSA(1.21g)分散在39.12g去离子水中，固体占水溶液的3.0wt％。测定分散体的电导率和发光性质。将商购的含100-150nm厚的ITO层的氧化锡铟(ITO)/玻璃板切成30mm×30mm的样品30。接着用氧等离子体蚀刻ITO层。将玻璃基底上用来测定电导率的ITO蚀刻成一系列平行ITO线，用作电极。将基底上要制成LED用于发光测定的ITO蚀刻成15mm×20mm的ITO层，作为阳极。然后以1200rpm的旋转速度将水分散体旋涂每块ITO/玻璃基底上。所得PAni/PAAMPSA层厚约137nm。
用于测定粘度的样品按如下方法制备：0.0989g PAni/PAAMPSA与9.9081g去离子水混合，PAni/PAAMPSA占分散体的0.99wt％。对混合物磁力搅拌过夜。应当指出，与本发明实施例4相比，尽管旋涂速度低(1200rpm对6000rpm)，本实施例的涂层厚度小于实施例4(137nm对300nm)。比较显示，所得分散体的粘度小于实施例4的分散体粘度。
涂有PAni/PAAMPSA的ITO/玻璃基底在90℃氮气中干燥30分钟，然后测定电导率。电导率是通过测定两个电极间的电阻来确定的，然后根据电阻、导电层厚度和用来测定电阻的两个电极间的距离计算得到3.6×10-5S/cm。电导率示于表1。
对于发光测定，当PAni/PAAMPSA层加入到发光二极管(LED)中时，其顶部涂有超黄发光聚(取代的亚苯基亚乙烯基)(PDY 131，购自Covion Company，Frankfurt，Germay)，作为活性电致发光(EL)层。EL层的厚度约为70nm。所有膜厚用TENCOR 500 Surface Profiler测定。对于阴极，在1.3×10-4Pa的压力下将Ba和Al层气相沉积到EL层上。Ba层的最终厚度为3nm；Ba层顶部的Al层厚度为300nm。LED器件的性能按如下方法测定。用Keithley InstrumentInc.(Cleveland，OH)生产的Keithley 236源—测量单元和带有校准硅光二极管的S370 Optometer(UDT Sensor，Inc.，Hawthorne，CA)测定电流—外加电压、发光亮度—外加电压和发光效率(坎德拉/安培-cd/A)。室温下给5个LED施加电流，电流密度为8.3mA/cm2。得到这种电流密度的平均电压为4.2伏，平均发光效率和发光亮度分别为8.3cd/A和115cd/m2，总结于表1。表1还列出了器件在80℃下，电流密度为3.3mA/cm2时的半寿期为12小时。
实施例1
本实施例说明了如何用氧化硅纳米微粒制备PAni/PAAMPSA水分散体，及其作为缓冲层的电导率和发光性质。
按比较例1所述方法制备的PAni/PAAMPSA(0.63g)与0.75gSnowtex-UP(0.75g，Nissan Chemical Industries，Ltd.，Tokyo，Japan)混合，Snowtex-UP含有0.152g氧化硅纳米微粒和24.07g去离子水。Snowtex-UP是pH为9.0-10.5的水分散体，氧化硅微粒宽约5-20nm，长约40-300nm。氧化硅∶PAni/PAAMPSA重量比为4.1∶1。
用和比较例1所述相同的方法测定分散体的电导率和发光性质。如表1所示结果，由实施例1的分散体铸塑而成的缓冲层的电导率比比较例1低(8.2×10-7S/cm对3.6×10-5S/cm)，半寿期比比较例1长(29小时对12小时)。此实施例表明纳米微粒在降低电导率和提高器件半寿期上的效应。
实施例2
本实施例说明了如何用胶体氧化硅制备PAni/PAAMPSA水分散体，及其作为缓冲层的电导率和发光性质。
按比较例1所述方法制备的PAni/PAAMPSA(0.61g)与Snowtex-O(0.75g，Nissan Chemical Industries，Ltd.，Tokyo，Japan)混合，Snowtex-O含有0.153g氧化硅纳米微粒和23.47g去离子水。Snowtex-O是pH为2-4的水分散体，氧化硅微粒粒度约为10-20nm。氧化硅∶PAni/PAAMPSA重量比为3.99∶1。
用和比较例1所述相同的方法测定分散体的电导率和发光性质。如表1所示结果，由实施例2的分散体铸塑而成的缓冲层的电导率比比较例1低(7.6×10-7S/cm对3.6×10-5S/cm)，半寿期比比较例1长(30小时对12小时)。此实施例表明纳米微粒在降低电导率和提高器件半寿期上的效应。
实施例3
此实施例说明了如何用半导电性氧化物制备PAni/PAAMPSA水分散体，及其作为缓冲层的电导率和发光性质。
按比较例1所述方法制备的PAni/PAAMPSA(0.90g)与CelnaxCX-Z300H(1.97g，Nissan Chemical Industries，Ltd.，Tokyo，Japan生产的锑酸锌)混合，Celnax CX-Z300H含有0.601g导电氧化物微粒和48.53g去离子水。Celnax CX-Z300H是pH为6.85的水分散体，氧化物纳米微粒约为20nm。在160Kg/cm2压力下在压制的干颗粒上测定氧化物粉的电导率为3.6S/cm。氧化物∶PAni/PAAMPSA重量比为1.50∶1。
用和比较例1所述相同的方法测定分散体的电导率和发光性质。如表1所示结果，由实施例3的分散体铸塑而成的缓冲层的电导率比比较例1低(8.3×10-8S/cm对3.6×10-5S/cm)，半寿期比比较例1长(61小时对12小时)。此实施例表明纳米微粒在降低电导率和提高器件半寿期上的效应。
实施例4
此实施例说明了在SiO2纳米微粒的存在下制备本发明的PAni/PAAMPSA水分散体，及其作为缓冲层的电导率和发光性质。
在SiO2纳米微粒存在下PAni/PAAMPSA的合成按如下方式进行。将PAAMPSA(36.32g 15wt％水溶液，购自Sigma-Aldrich Corp.，St.Louis，MO，USA)加入到250 Nalgene塑料瓶中。向PAni/PAAMPSA溶液中加入Snowtex-UP(34.33g，购自Nissan Chemical Industries，Ltd.，Tokyo，Japan)。Snowtex-UP是pH为9.0-10.5的水分散体，氧化硅微粒宽约5-20nm，长约40-300nm。将PAAMPSA/Snowtex-UP氧化硅混合物分散在去离子水(150ml)中。向此分散体中加入苯胺(4.08g)。将PAAMPSA/Snowtex-UP/苯胺的水性混合物装入500ml四颈圆底烧瓶中，用冰/水浴冷却到约4℃。用磁力搅拌器连续搅拌溶液。向冷却的PAAMPSA/Snowtex-UP/苯胺分散体中，在1小时时间内加入100ml含有4.493g PAAMPSA(同上)和2.33g过硫酸铵的水溶液。反应进行180分钟。
然后将反应混合物倒入两个离心瓶中，在15℃下以8000rpm的速度离心30分钟。离心之后，将上清液缓慢倒入丙酮，沉淀出聚合物产物。沉淀之后，用丙酮反复冲洗固体聚合物，过滤，在真空炉(约18Hg.，通N2，室温)中干燥过夜，产率为14.19g。应当指出，这里的产率几乎是比较例1的产率的2倍。产率的提高表明SiO2纳米微粒存在于PAni/PAAMPSA内部。
将PAni/PAAMPSA/SiO2(1.20g，上面制备的)分散在38.80g去离子水中，固体占水溶液的3.0wt％。如前面实施例所述，将缓冲层铸塑到ITO基底上。对于发光测定，在PAni/PAAMPSA/氧化硅层顶部上涂布超黄发光聚(取代的亚苯基亚乙烯基)(PDY 131，购自Covion Company，Frankfurt，Germay)，作为LED器件中的活性电致发光(EL)层。EL层的厚度约为70nm。所有膜厚利用TENCOR500 Surface Profiler测定。对于阴极，在1.3×10-4Pa的真空下将Ba和Al层气相沉积到EL层上。Ba层的最终厚度为3nm；Ba层顶部的Al层厚度为300nm。LED器件的性能按如下方法测定。用Keithley Instrument Inc.(Cleveland，OH)制造的Keithley 236源—测量单元和带有校准硅光二极管的S370 Optometer(UDTSensor，Inc.，Hawthorne，CA)测定电流—外加电压、发光亮度—外加电压和发光效率(坎德拉/安培-cd/A)。室温下给5个LED器件的每个器件施加电流，电流密度为8.3mA/cm2。得到这种电流密度的平均电压为4.3伏，平均发光效率和发光亮度分别为5.3cd/A和130cd/m2，总结于表1。表1还列出了器件在80℃下，电流密度为3.3mA/cm2时的半寿期为42小时。应当指出，与比较例1中不含氧化硅的PAni/PAAMPSA相比，尽管厚度是比较例1的2.2倍，本实施例的半寿期仍然提高了4倍，而且发光强度更高(130cd/m2对115cd/m2)。
                           表1
        在PAni/PAAMPSA中加入无机纳米微粒对玻璃基底上
                    OLED发光性质的影响
实施例   涂层厚度s(nm)   电导率(S/cm)   电压(伏)@8.3mA/cm2   发光效率(Cd/A)@8.3mA/cm2 亮度(Cd/m2)@3.3mA/cm280℃ 半寿期(hr)@3.3mA/cm280℃
比较例1   137@1200rpm   3.6×10-5     4.2     8.3     115     12
实施例1   114@1200rpm   8.2×10-7     4.8     8.1     135     29
实施例2   166@1200rpm   7.6×10-7     4.9     7.4     108     30
实施例3   113@1200rpm   8.3×10-8     4.1     8.0     148     61
实施例4   300@6000rpm   9.0×10-7     4.3     5.3     130     42
如表2所示，实施例4的水分散体在6000rpm的旋转速度下得到300nm的涂层厚度。该涂层厚度比比较例1的厚度高得多(300nm对137nm)，虽然其旋涂速度高(6000rpm对1200rpm)。比较显示，用氧化硅纳米微粒聚合的PAni/PAAMPSA比不用氧化硅纳米微粒聚合的PAni/PAAMPSA具有更高的粘度。如表2所示，粘度的增加导致了缓冲层厚度的增加。用于测定粘度的分散体用如下方法制备：0.0999g PAni/PAAMPSA/氧化硅与9.9164g去离子水混合，PAni/PAAMPSA/氧化硅在分散体中占1.00wt％。
                   表2
         PAni/PAAMPSA水分散体的粘度
              粘度(cps)
    样品     10s-1     100s-1     1000s-1
  比较例1     5.50     4.52     4.10
  实施例4     8.30     6.80     6.15
实施例5
本实施例说明了由市售PEDT水分散体在有机溶剂中制备的固体膜的整体性。
在此实施例中，在室温和氮气流下，在玻璃烧杯中将市售PEDT水分散体(Baytron-P VP Al 4083，购自H.C.Starck，GmbH，Leverkusen，Germany)干燥成固体膜，其中PEDT水分散体的电导率约为10-3S/cm。干燥膜与薄膜场效应晶体管的生产中用来溶解有机半导电聚合物的普通有机溶剂(如甲苯、氯仿、二氯甲烷等)混合。膜片既没有为有机液体所膨胀，也没有使液体褪色。这个结果清楚地表明，用Baytron-P制备的PEDT膜与半导电聚合物用有机溶剂相容，因而可以用作薄膜场效应晶体管。
实施例6
本实施例说明了由PAni/PAAMPSA水分散体在有机溶剂中的水分散体制备的固体膜的整体性。
在此实施例中，在室温和氮气流下，在玻璃烧杯中将比较例1制备的PAni/PAAMPSA水分散体干燥成固体膜。干燥膜与薄膜场效应晶体管的生产中用来溶解有机半导电聚合物的普通有机溶剂混合(如甲苯、氯仿、二氯甲烷等)混合。膜片既没有为有机液体所膨胀，也没有使液体脱色。这个结果清楚地表明，用PAni/PAAMPSA水分散体制备的PAni/PAAMPSA膜与半导电聚合物用有机溶剂相容，因而可以用作薄膜场效应晶体管。
实施例7
本实施例说明了含有聚苯胺/聚酸或聚(二氧亚乙基噻吩)/聚酸和强导电纳米微粒的水分散体的制备。
如比较例1所述，由PAni/PAAMPSA水分散体铸塑而成的PAni/PAAMPSA的电导率仅为3.6×10-5S/cm，它不足以用作薄膜场效应晶体管的栅极、漏极和源极。用PAni水分散体，例如Ormecon(Ammersbeck，Germany)或PEDT水分散体，例如Baytron-P曾经得到的最高电导率约为10-3S/cm，对于实际应用来说仍太低。但是，使用本发明含有纳米微粒，如金属纳米线或纳米微粒或纳米碳管的导电聚合物水分散体可极大提高用这些水分散体铸塑而成的电极的电导率。例如，直径为15nm、电导率为1.7×104S/cm的金属钼线可用来提高电导率。直径为8nm、长20μm、电导率为60S/cm的碳纳米管也可用来提高电导率。由于纳米微粒具有高电导率，且微粒在水中有很好的分散性，由导电聚合物和强导电纳米微粒组成的复合水分散体很容易用来制备连续光滑膜，用作薄膜场效应晶体管的漏极、源极或栅极。
虽然已经结合特定的优选实施方式对本发明进行了详细介绍，但应当理解，各种改进和变化形式包括在在所叙述及权利所要求的主旨和范围之内。

Claims (8)

1.一种包含导电有机聚合物和许多纳米微粒的水分散体的组合物。
2.权利要求1所述组合物，其特征在于，所述导电有机聚合物选自以聚(2-丙烯酰氨基-2-甲基-1-丙烷磺酸)为反离子的聚苯胺(PAni/PAAMPSA)和以聚(苯乙烯磺酸)为反离子的聚(亚乙基二氧噻吩)(PEDT/PSS)。
3.权利要求1所述组合物，其特征在于所述纳米微粒是无机纳米微粒、有机纳米微粒或它们的混合物。
4.权利要求3所述组合物，其特征在于所述无机纳米微粒选自氧化硅、氧化铝、导电金属氧化物及其混合物，有机纳米微粒选自聚丙烯酸酯、碳纳米管和全氟亚乙基磺酸酯和它们的混合物。
5.一种将薄膜场效应晶体管电极的电导率提高到大于约10-3S/cm的方法，所述电极用水分散体在基底上铸塑而成，所述方法包括在所述导电有机聚合物的水分散体中加入许多纳米微粒。
6.有机电子器件，它至少具有一层用以下方法制备的层：在导电有机聚合物的水分散体中加入许多纳米微粒，将所述水分散体铸塑在基底上形成所述层。
7.权利要求6所述器件，其特征在于，该器件是光传感器、光开关、光致抗蚀剂、光电阻、光电晶体管、光电管、IR检测器、光伏打电池、太阳能电池、发光二极管、生物传感器、发光二极管显示器或二极管激光器。
8.高电阻缓冲层，它包含导电聚合物和许多分散在其中的纳米微粒，其中所述导电聚合物包含至少一种选自下列的导电聚合物：以聚(2-丙烯酰氨基-2-甲基-1-丙烷磺酸)为反离子的聚苯胺(PAni/PAAMPSA)和以聚(苯乙烯磺酸)为反离子的聚(亚乙基二氧噻吩)(PEDT/PSS)，所述有机纳米微粒选自聚丙烯酸酯、碳纳米管和全氟亚乙基磺酸酯及其混合物。
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102187747A (zh) * 2008-11-12 2011-09-14 柯达公司 聚合物导电供体和转移方法
CN102378773A (zh) * 2009-01-30 2012-03-14 惠普开发有限公司 聚合物和聚合物-纳米粒子组合物
CN102395627A (zh) * 2009-04-24 2012-03-28 E.I.内穆尔杜邦公司 导电聚合物组合物和由其制得的膜
CN101568617B (zh) * 2006-11-01 2013-05-01 维克森林大学 固态照明组合物和系统
CN103633244A (zh) * 2012-08-21 2014-03-12 索尼公司 半导体器件及其制造方法以及电子装置

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101148285B1 (ko) * 2002-09-24 2012-05-21 이 아이 듀폰 디 네모아 앤드 캄파니 전기적 응용을 위한 중합체성 산 콜로이드로 제조된수분산성 폴리아닐린
JP4464277B2 (ja) * 2002-09-24 2010-05-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法
DE60322923D1 (de) * 2002-09-24 2008-09-25 Du Pont Wasserdispergierbare polythiophene hergestellt untäuren
US7317047B2 (en) 2002-09-24 2008-01-08 E.I. Du Pont De Nemours And Company Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
JP3913208B2 (ja) * 2002-11-01 2007-05-09 三菱レイヨン株式会社 カーボンナノチューブ含有組成物、これからなる塗膜を有する複合体、及びそれらの製造方法
KR100720628B1 (ko) * 2002-11-01 2007-05-21 미츠비시 레이온 가부시키가이샤 탄소 나노튜브 함유 조성물, 이를 포함하는 도막을 갖는복합체, 및 이들의 제조 방법
JP4394890B2 (ja) * 2003-03-10 2010-01-06 株式会社Ｋｒｉ 導電性組成物、導電膜、樹脂複合材料
JP4851323B2 (ja) * 2003-04-22 2012-01-11 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 高分子酸コロイドにより製造された水分散性ポリチオフェン
US7390438B2 (en) 2003-04-22 2008-06-24 E.I. Du Pont De Nemours And Company Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids
DE10325102B3 (de) * 2003-06-03 2004-05-27 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Dispersionen steifkettiger, konjugierter Polymere, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung elektronischer Bauelemente
US7351358B2 (en) 2004-03-17 2008-04-01 E.I. Du Pont De Nemours And Company Water dispersible polypyrroles made with polymeric acid colloids for electronics applications
US8147962B2 (en) * 2004-04-13 2012-04-03 E. I. Du Pont De Nemours And Company Conductive polymer composites
KR100632632B1 (ko) 2004-05-28 2006-10-12 삼성전자주식회사 나노 결정의 다층 박막 제조 방법 및 이를 이용한유·무기 하이브리드 전기 발광 소자
KR100736521B1 (ko) 2004-06-09 2007-07-06 삼성전자주식회사 나노 결정 전기발광 소자 및 그의 제조방법
KR20060004158A (ko) * 2004-07-08 2006-01-12 박철용 피티씨 특성을 갖는 수성 도전성 중합체 조성물 및 그제조방법
JP4534674B2 (ja) * 2004-08-31 2010-09-01 日産自動車株式会社 機能性薄膜素子、機能性薄膜素子の製造方法及び機能性薄膜素子を用いた物品
JP4534673B2 (ja) * 2004-08-31 2010-09-01 日産自動車株式会社 機能性薄膜素子、機能性薄膜素子の製造方法及び機能性薄膜素子を用いた物品
JP4824971B2 (ja) * 2004-09-09 2011-11-30 三菱レイヨン株式会社 ナノ物質含有組成物、その製造方法及びそれを用いた複合体
KR101195714B1 (ko) 2004-09-09 2012-10-29 미츠비시 레이온 가부시키가이샤 나노물질 함유 조성물, 그의 제조방법 및 그를 이용한복합체
EP1653529B1 (en) * 2004-10-11 2007-11-21 Samsung SDI Co., Ltd. Organic electroluminescent device and method of manufacturing the same
KR20060064987A (ko) * 2004-12-09 2006-06-14 한국전자통신연구원 전도성 잉크와 이를 이용한 유기 반도체 트랜지스터 및 그제작 방법
US20060291142A1 (en) * 2004-12-13 2006-12-28 Ohio State University Research Foundation Composite material containing nanotubes and an electrically conductive polymer
DE102005010162B4 (de) 2005-03-02 2007-06-14 Ormecon Gmbh Leitfähige Polymere aus Teilchen mit anisotroper Morphologie
KR101290099B1 (ko) 2005-03-23 2013-07-26 가부시키가이샤 한도오따이 에네루기 켄큐쇼 복합재료, 발광소자용 재료, 발광소자, 발광장치 및전자기기
JP2006286664A (ja) 2005-03-31 2006-10-19 Toshiba Corp 有機エレクトロルミネッセンス素子
US7593004B2 (en) 2005-06-02 2009-09-22 Eastman Kodak Company Touchscreen with conductive layer comprising carbon nanotubes
US7535462B2 (en) 2005-06-02 2009-05-19 Eastman Kodak Company Touchscreen with one carbon nanotube conductive layer
US7645497B2 (en) 2005-06-02 2010-01-12 Eastman Kodak Company Multi-layer conductor with carbon nanotubes
JP4856900B2 (ja) * 2005-06-13 2012-01-18 パナソニック株式会社 電界効果トランジスタの製造方法
WO2007002740A2 (en) * 2005-06-28 2007-01-04 E. I. Du Pont De Nemours And Company Buffer compositions
CN101208369B (zh) * 2005-06-28 2013-03-27 E.I.内穆尔杜邦公司 高功函数透明导体
JP5753338B2 (ja) * 2005-07-01 2015-07-22 ナショナル ユニヴァーシティー オブ シンガポール 導電性複合材料
EP1962348B1 (en) * 2005-08-12 2013-03-06 Cambrios Technologies Corporation Nanowires-based transparent conductors
DE102005039608A1 (de) * 2005-08-19 2007-03-01 Ormecon Gmbh Zusammensetzung mit intrinsisch leitfähigem Polymer
US8216680B2 (en) 2006-02-03 2012-07-10 E I Du Pont De Nemours And Company Transparent composite conductors having high work function
AU2007248170B2 (en) 2006-05-01 2012-08-16 Arrowhead Center, Inc. Fiber photovoltaic devices and applications thereof
SI2022108T1 (sl) * 2006-05-01 2009-10-31 Univ Wake Forest Organske optoelektronske naprave in uporabe le-teh
US8679630B2 (en) * 2006-05-17 2014-03-25 Purdue Research Foundation Vertical carbon nanotube device in nanoporous templates
US7625637B2 (en) * 2006-05-31 2009-12-01 Cabot Corporation Production of metal nanoparticles from precursors having low reduction potentials
KR101386216B1 (ko) * 2006-06-07 2014-04-18 삼성디스플레이 주식회사 유기 발광 소자
US7796123B1 (en) 2006-06-20 2010-09-14 Eastman Kodak Company Touchscreen with carbon nanotube conductive layers
US20080149178A1 (en) * 2006-06-27 2008-06-26 Marisol Reyes-Reyes Composite organic materials and applications thereof
JP4301260B2 (ja) * 2006-07-06 2009-07-22 セイコーエプソン株式会社 有機ｅｌ装置の製造方法及び電子機器
EP2378581B1 (en) 2006-08-07 2013-07-31 Wake Forest University Photovoltaic Cell
JP5161446B2 (ja) * 2006-08-22 2013-03-13 帝人デュポンフィルム株式会社 導電性フィルムおよび当該フィルムを用いたタッチパネル
WO2008033388A2 (en) * 2006-09-12 2008-03-20 Qd Vision, Inc. A composite including nanoparticles, methods, and products including a composite
ATE546032T1 (de) * 2006-09-13 2012-03-15 Enthone Artikel mit beschichtung aus elektrisch leitendem polymer und edel-/halbedelmetal sowie herstellungsverfahren dafür
JP5186757B2 (ja) * 2006-11-27 2013-04-24 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子の製造方法、有機エレクトロルミネッセンス素子、表示装置及び照明装置
US8153029B2 (en) 2006-12-28 2012-04-10 E.I. Du Pont De Nemours And Company Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof
US8062553B2 (en) 2006-12-28 2011-11-22 E. I. Du Pont De Nemours And Company Compositions of polyaniline made with perfuoropolymeric acid which are heat-enhanced and electronic devices made therewith
US20080191172A1 (en) 2006-12-29 2008-08-14 Che-Hsiung Hsu High work-function and high conductivity compositions of electrically conducting polymers
US7785496B1 (en) 2007-01-26 2010-08-31 Clemson University Research Foundation Electrochromic inks including conducting polymer colloidal nanocomposites, devices including the electrochromic inks and methods of forming same
US9487877B2 (en) * 2007-02-01 2016-11-08 Purdue Research Foundation Contact metallization of carbon nanotubes
US20080251768A1 (en) 2007-04-13 2008-10-16 Che-Hsiung Hsu Electrically conductive polymer compositions
DE102007018540A1 (de) * 2007-04-19 2008-10-30 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Elektrisch leitfähige und transparente Zusammensetzung
JP2008277648A (ja) * 2007-05-02 2008-11-13 Seiko Epson Corp 有機ｅｌ素子及び有機ｅｌ素子の製造方法
US8241526B2 (en) * 2007-05-18 2012-08-14 E I Du Pont De Nemours And Company Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives
JP5618458B2 (ja) * 2007-08-10 2014-11-05 住友化学株式会社 有機エレクトロルミネッセンス素子、製造方法及び塗布液
US7994105B2 (en) * 2007-08-11 2011-08-09 Jagdish Narayan Lubricant having nanoparticles and microparticles to enhance fuel efficiency, and a laser synthesis method to create dispersed nanoparticles
US7947202B2 (en) * 2007-08-20 2011-05-24 Board Of Regents, The University Of Texas System Polymer-nanoparticle compositions and methods of making and using same
JP4936069B2 (ja) * 2007-10-31 2012-05-23 株式会社デンソー モータ制御装置
US20100307580A1 (en) * 2007-11-01 2010-12-09 David Loren Carroll Lateral Organic Optoelectronic Devices And Applications Thereof
JP5096885B2 (ja) * 2007-11-19 2012-12-12 公立大学法人大阪府立大学 有機化合物およびシリカナノ粒子からなる組成物。
CN101911332B (zh) * 2007-12-28 2012-06-13 夏普株式会社 有机电致发光元件
KR20090092051A (ko) 2008-02-26 2009-08-31 삼성모바일디스플레이주식회사 유기전계발광소자 및 그의 제조방법
KR100891489B1 (ko) * 2008-02-28 2009-04-06 경북대학교 산학협력단 나노다공성 실리카-폴리아닐린 혼성 물질
EP2268736A1 (en) * 2008-03-19 2011-01-05 E. I. du Pont de Nemours and Company Electrically conductive polymer compositions and films made therefrom
KR20110044240A (ko) * 2008-07-22 2011-04-28 이 아이 듀폰 디 네모아 앤드 캄파니 무기 나노입자를 포함하는 전기전도성 중합체의 수성 분산액
WO2010027955A2 (en) 2008-09-02 2010-03-11 Natrix Separations Inc. Chromatography membranes, devices containing them, and methods of use thereof
JP5243181B2 (ja) 2008-10-20 2013-07-24 スリーエム イノベイティブ プロパティズ カンパニー 導電性高分子複合体及び導電性高分子材料を用いた熱電素子
TWI422088B (zh) * 2008-10-23 2014-01-01 Nat Univ Tsing Hua 具有奈米點之有機發光二極體及其製造方法
US8461758B2 (en) * 2008-12-19 2013-06-11 E I Du Pont De Nemours And Company Buffer bilayers for electronic devices
US8715981B2 (en) 2009-01-27 2014-05-06 Purdue Research Foundation Electrochemical biosensor
US8785004B2 (en) 2009-01-30 2014-07-22 Hewlett-Packard Development Company, L.P. UV light-emissive fluorene-based copolymers
WO2010087841A1 (en) 2009-01-30 2010-08-05 Hewlett-Packard Development Company Block copolymers and block copolymer nanoparticle compositions
TW201100480A (en) 2009-03-12 2011-01-01 Du Pont Electrically conductive polymer compositions for coating applications
BRPI0901577B1 (pt) * 2009-04-01 2020-02-18 Universidade Federal De Pernambuco Dispositivo semicondutor nanoestruturado do tipo varistor constituído de polímero condutor e óxido de zinco e metais
US8872154B2 (en) 2009-04-06 2014-10-28 Purdue Research Foundation Field effect transistor fabrication from carbon nanotubes
US9536633B2 (en) 2009-04-10 2017-01-03 Sumitomo Chemical Company, Limited Metallic composite and composition thereof
WO2010117075A1 (ja) * 2009-04-10 2010-10-14 住友化学株式会社 金属複合体及びその組成物
US8845933B2 (en) 2009-04-21 2014-09-30 E I Du Pont De Nemours And Company Electrically conductive polymer compositions and films made therefrom
JP5740830B2 (ja) * 2010-04-05 2015-07-01 住友化学株式会社 金属複合体及びそれに有用な化合物
EP3427815B1 (en) 2011-05-17 2023-12-06 Merck Millipore Ltd. Device with layered tubular membranes for chromatography
KR101302786B1 (ko) * 2011-05-27 2013-09-03 포항공과대학교 산학협력단 높은 일함수를 가지는 고분자 전극을 채용한 단순화된 유기 전자 소자
ES2648364T3 (es) 2011-12-19 2018-01-02 Inoviscoat Gmbh Elementos luminosos con una disposición electroluminiscente así como procedimiento para la producción de un elemento luminoso
WO2015077792A1 (en) * 2013-11-25 2015-05-28 Georgetown University Electronic devices with organic nanoparticles
CN103840074A (zh) * 2014-02-12 2014-06-04 中国科学院化学研究所 一种聚吡咯包覆碳纳米管的复合热电材料的制备方法
EP3886194A3 (en) 2014-11-18 2021-10-20 Heraeus Deutschland GmbH & Co KG Fluorinated aromatic small molecules as functional additives for dispersion of conductive polymers
CN105118934B (zh) * 2015-09-17 2017-03-15 京东方科技集团股份有限公司 不平坦粒子层制备方法、有机电致发光器件和显示装置
US11111586B2 (en) 2016-02-23 2021-09-07 South Dakota Board Of Regents Self-organized and electrically conducting PEDOT polymer matrix for applications in sensors and energy generation and storage
KR20180096248A (ko) 2017-02-21 2018-08-29 영남대학교 산학협력단 유기박막 트랜지스터 소스-드레인 전극 형성용 조성물
JP7099458B2 (ja) * 2017-06-20 2022-07-12 日産化学株式会社 非水系インク組成物
KR20190081698A (ko) 2017-12-29 2019-07-09 박성민 2d-pani 분산법을 적용한 도전성 코팅액
US11339246B2 (en) 2020-03-03 2022-05-24 Lg Energy Solution, Ltd. Preparation method of polymer
US11773212B2 (en) 2020-03-03 2023-10-03 Lg Energy Solution, Ltd. Preparation method of polymer
KR102481440B1 (ko) * 2020-11-13 2022-12-26 부경대학교 산학협력단 전도성 고분자의 합성 방법 및 전도성 고분자 박막의 제조방법

Family Cites Families (167)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282875A (en) * 1964-07-22 1966-11-01 Du Pont Fluorocarbon vinyl ether polymers
US4358545A (en) 1980-06-11 1982-11-09 The Dow Chemical Company Sulfonic acid electrolytic cell having flourinated polymer membrane with hydration product less than 22,000
US4433082A (en) * 1981-05-01 1984-02-21 E. I. Du Pont De Nemours And Company Process for making liquid composition of perfluorinated ion exchange polymer, and product thereof
US5378402A (en) 1982-08-02 1995-01-03 Raychem Limited Polymer compositions
US4552927A (en) 1983-09-09 1985-11-12 Rockwell International Corporation Conducting organic polymer based on polypyrrole
US4731408A (en) * 1985-12-20 1988-03-15 Polaroid Corporation Processable conductive polymers
US4940525A (en) * 1987-05-08 1990-07-10 The Dow Chemical Company Low equivalent weight sulfonic fluoropolymers
US4795543A (en) * 1987-05-26 1989-01-03 Transducer Research, Inc. Spin coating of electrolytes
US5069820A (en) 1987-08-07 1991-12-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
US5160457A (en) 1987-08-07 1992-11-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
JPH01132052A (ja) * 1987-08-10 1989-05-24 Nitto Denko Corp 導電性有機重合体電池
DE3843412A1 (de) 1988-04-22 1990-06-28 Bayer Ag Neue polythiophene, verfahren zu ihrer herstellung und ihre verwendung
FR2632979B1 (fr) 1988-06-16 1990-09-21 Commissariat Energie Atomique Procede de preparation d'un polymere conducteur mixte ionique et electronique et polymeres obtenus par ce procede
US4973391A (en) * 1988-08-30 1990-11-27 Osaka Gas Company, Ltd. Composite polymers of polyaniline with metal phthalocyanine and polyaniline with organic sulfonic acid and nafion
GB8909011D0 (en) 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
EP0440957B1 (de) 1990-02-08 1996-03-27 Bayer Ag Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung
DE69110922T2 (de) 1990-02-23 1995-12-07 Sumitomo Chemical Co Organisch elektrolumineszente Vorrichtung.
US5185100A (en) * 1990-03-29 1993-02-09 Allied-Signal Inc Conductive polymers formed from conjugated backbone polymers doped with non-oxidizing protonic acids
BE1008036A3 (fr) 1990-08-30 1996-01-03 Solvay Melanges de polymeres polaires et de polymeres conducteurs dedopes, procedes d'obtention de ces melanges et utilisation de ces melanges pour fabriquer des dispositifs electroniques optoelectriques, electrotechniques et electromecaniques.
FR2666443A1 (fr) * 1990-08-31 1992-03-06 Commissariat Energie Atomique Materiau a base de polymere conducteur electronique comprenant des particules magnetiques et son procede de fabrication.
JP3056522B2 (ja) * 1990-11-30 2000-06-26 三菱レイヨン株式会社 金属―導電性高分子複合微粒子及びその製造方法
US5463005A (en) * 1992-01-03 1995-10-31 Gas Research Institute Copolymers of tetrafluoroethylene and perfluorinated sulfonyl monomers and membranes made therefrom
DE4334390C2 (de) 1993-10-08 1999-01-21 Nat Science Council Verfahren zur Herstellung eines verarbeitbaren, leitfähigen, kolloidalen Polymeren
US5537000A (en) * 1994-04-29 1996-07-16 The Regents, University Of California Electroluminescent devices formed using semiconductor nanocrystals as an electron transport media and method of making such electroluminescent devices
JP2001506393A (ja) 1994-09-06 2001-05-15 フィリップス エレクトロニクス ネムローゼ フェンノートシャップ 導電性ポリマー製の透明な構造を付与した電極層を有するエレクトロルミネセント装置
US5567356A (en) * 1994-11-07 1996-10-22 Monsanto Company Emulsion-polymerization process and electrically-conductive polyaniline salts
JP3798484B2 (ja) * 1995-11-15 2006-07-19 インターナショナル・ビジネス・マシーンズ・コーポレーション 架橋導電性ポリマー及びその前駆物質
DE19543205A1 (de) * 1995-11-20 1997-05-22 Bayer Ag Zwischenschicht in elektrolumineszierenden Anordnungen enthaltend feinteilige anorganische Partikel
US5798170A (en) * 1996-02-29 1998-08-25 Uniax Corporation Long operating life for polymer light-emitting diodes
DE69705854T2 (de) * 1996-10-15 2002-04-11 Du Pont Hochfluorierte ionenaustauscher-polymerteilchen enthaltende zusammensetzungen
JP2000505249A (ja) * 1996-11-12 2000-04-25 インターナシヨナル・ビジネス・マシーンズ・コーポレーシヨン 導電性ポリマーのパターンおよび電極または電気接点としてのその応用
US6171522B1 (en) 1996-12-30 2001-01-09 Hydro-Qu{acute over (e)}bec Heterocyclic aromatic anion salts, and their uses as ionic conducting materials
AU5826498A (en) 1997-01-22 1998-08-07 E.I. Du Pont De Nemours And Company Grafting of polymers with fluorocarbon compounds
EP1026152B1 (en) 1997-03-31 2006-07-26 Daikin Industries, Limited Process for producing perfluorovinyl ethersulfonic acid derivatives
US6599631B2 (en) 2001-01-26 2003-07-29 Nanogram Corporation Polymer-inorganic particle composites
US6303238B1 (en) * 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
WO1999023672A1 (en) 1997-11-05 1999-05-14 Koninklijke Philips Electronics N.V. Conjugated polymer in an oxidized state
DE19757542A1 (de) * 1997-12-23 1999-06-24 Bayer Ag Siebdruckpaste zur Herstellung elektrisch leitfähiger Beschichtungen
EP1055260A1 (en) * 1998-02-02 2000-11-29 Uniax Corporation Organic diodes with switchable photosensitivity
US6866946B2 (en) * 1998-02-02 2005-03-15 Dupont Displays, Inc. High resistance polyaniline useful in high efficiency pixellated polymer electronic displays
US6100324A (en) 1998-04-16 2000-08-08 E. I. Du Pont De Nemours And Company Ionomers and ionically conductive compositions
JP3937113B2 (ja) * 1998-06-05 2007-06-27 日産化学工業株式会社 有機−無機複合導電性ゾル及びその製造法
US6210790B1 (en) * 1998-07-15 2001-04-03 Rensselaer Polytechnic Institute Glass-like composites comprising a surface-modified colloidal silica and method of making thereof
US6097147A (en) * 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
US6830828B2 (en) 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6187522B1 (en) * 1999-03-25 2001-02-13 Eastman Kodak Company Scratch resistant antistatic layer for imaging elements
US20040217877A1 (en) 1999-05-04 2004-11-04 William Kokonaski Flexible electronic display and wireless communication system
CN100407448C (zh) 1999-05-13 2008-07-30 普林斯顿大学理事会 基于电致磷光的极高效有机发光器件
US20020099119A1 (en) * 1999-05-27 2002-07-25 Bradley D. Craig Water-borne ceramer compositions and antistatic abrasion resistant ceramers made therefrom
KR100302326B1 (ko) * 1999-06-09 2001-09-22 윤덕용 폴리비닐알콜-실란커플링제를 이용한 무-유기 공중합체 및 그의제조방법
JP2001006878A (ja) 1999-06-22 2001-01-12 Matsushita Electric Ind Co Ltd 薄膜ｅｌ素子およびその駆動方法
US6324091B1 (en) 2000-01-14 2001-11-27 The Regents Of The University Of California Tightly coupled porphyrin macrocycles for molecular memory storage
US6620494B2 (en) * 1999-07-03 2003-09-16 Ten Cate Enbi B.V. Conductive roller
US6593690B1 (en) 1999-09-03 2003-07-15 3M Innovative Properties Company Large area organic electronic devices having conducting polymer buffer layers and methods of making same
AU1662601A (en) * 1999-11-24 2001-06-04 Tda Research, Inc. Combustion synthesis of single walled nanotubes
JP3656244B2 (ja) 1999-11-29 2005-06-08 株式会社豊田中央研究所 高耐久性固体高分子電解質及びその高耐久性固体高分子電解質を用いた電極−電解質接合体並びにその電極−電解質接合体を用いた電気化学デバイス
KR100794975B1 (ko) 1999-12-01 2008-01-16 더 트러스티즈 오브 프린스턴 유니버시티 유기 ｌｅｄ용 인광성 도펀트로서 ｌ2ｍｘ 형태의 착물
KR20020069199A (ko) 1999-12-02 2002-08-29 듀폰 디스플레이즈, 인크. 고효율 픽셀화 중합체 전자 디스플레이에 유용한 고저항의폴리아닐린
US6821645B2 (en) * 1999-12-27 2004-11-23 Fuji Photo Film Co., Ltd. Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex
JP2001270999A (ja) * 2000-01-19 2001-10-02 Mitsubishi Rayon Co Ltd 架橋性導電性組成物、耐水性導電体及びその形成方法
KR20010095437A (ko) * 2000-03-30 2001-11-07 윤덕용 발광물질/점토 나노복합소재를 이용한 유기 전기 발광 소자
US6706963B2 (en) * 2002-01-25 2004-03-16 Konarka Technologies, Inc. Photovoltaic cell interconnection
JP2001325831A (ja) * 2000-05-12 2001-11-22 Bando Chem Ind Ltd 金属コロイド液、導電性インク、導電性被膜及び導電性被膜形成用基底塗膜
US20020036291A1 (en) 2000-06-20 2002-03-28 Parker Ian D. Multilayer structures as stable hole-injecting electrodes for use in high efficiency organic electronic devices
CA2410535A1 (en) 2000-06-20 2001-12-27 Dupont Displays, Inc. High resistance conductive polymers for use in high efficiency pixellated organic electronic devices
US20020038999A1 (en) * 2000-06-20 2002-04-04 Yong Cao High resistance conductive polymers for use in high efficiency pixellated organic electronic devices
US6632472B2 (en) * 2000-06-26 2003-10-14 Agfa-Gevaert Redispersable latex comprising a polythiophene
EP1780233B1 (en) 2000-06-26 2009-06-17 Agfa-Gevaert Redispersible latex comprising a polythiophene
US6670645B2 (en) 2000-06-30 2003-12-30 E. I. Du Pont De Nemours And Company Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
KR100884039B1 (ko) 2000-08-11 2009-02-19 더 트러스티즈 오브 프린스턴 유니버시티 유기 금속 화합물 및 방사-이동 유기 전기인광
JP2002082082A (ja) * 2000-09-07 2002-03-22 Matsushita Refrig Co Ltd 臭気センサー及びその製造方法
JP4154139B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 発光素子
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 金属配位化合物
US7579112B2 (en) * 2001-07-27 2009-08-25 A123 Systems, Inc. Battery structures, self-organizing structures and related methods
US6515314B1 (en) * 2000-11-16 2003-02-04 General Electric Company Light-emitting device with organic layer doped with photoluminescent material
EP1231251A1 (en) * 2001-02-07 2002-08-14 Agfa-Gevaert Thin film inorganic light emitting diode
JP4300028B2 (ja) * 2001-02-08 2009-07-22 旭化成株式会社 有機ドメイン／無機ドメイン複合材料及びその用途
US6756474B2 (en) 2001-02-09 2004-06-29 E. I. Du Pont De Nemours And Company Aqueous conductive dispersions of polyaniline having enhanced viscosity
JP2002293888A (ja) 2001-03-29 2002-10-09 Fuji Photo Film Co Ltd 新規重合体、それを利用した発光素子用材料および発光素子
DE10126860C2 (de) 2001-06-01 2003-05-28 Siemens Ag Organischer Feldeffekt-Transistor, Verfahren zu seiner Herstellung und Verwendung zum Aufbau integrierter Schaltungen
US6784016B2 (en) * 2001-06-21 2004-08-31 The Trustees Of Princeton University Organic light-emitting devices with blocking and transport layers
US6875523B2 (en) * 2001-07-05 2005-04-05 E. I. Du Pont De Nemours And Company Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine N-oxides, and phosphine oxide-pyridine N-oxides, and devices made with such complexes
US6777515B2 (en) 2001-07-13 2004-08-17 I. Du Pont De Nemours And Company Functional fluorine-containing polymers and ionomers derived therefrom
EP1451245B1 (en) 2001-07-13 2006-08-30 E.I. Du Pont De Nemours And Company Process for dissolution of highly fluorinated ion-exchange polymers
CN1533395A (zh) 2001-07-18 2004-09-29 E.I.���¶��Ű˾ 含亚胺配体的发光镧系配合物和用这种配合物制备的器件
US6627333B2 (en) 2001-08-15 2003-09-30 Eastman Kodak Company White organic light-emitting devices with improved efficiency
US7112368B2 (en) * 2001-11-06 2006-09-26 E. I. Du Pont De Nemours And Company Poly(dioxythiophene)/poly(acrylamidoalkyslufonic acid) complexes
US7166368B2 (en) * 2001-11-07 2007-01-23 E. I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
AU2002356479A1 (en) 2001-11-30 2003-06-10 Acreo Ab Electrochemical sensor
EP1326260A1 (en) * 2001-12-11 2003-07-09 Agfa-Gevaert Material for making a conductive pattern
JP2003187983A (ja) 2001-12-17 2003-07-04 Ricoh Co Ltd 有機ｅｌトランジスタ
JP4299144B2 (ja) 2001-12-26 2009-07-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー フッ素化フェニルピリジン、フェニルピリミジン、およびフェニルキノリンを含むエレクトロルミネッセンスイリジウム化合物ならびにこのような化合物を用いて製造されるデバイス
JP2003217862A (ja) 2002-01-18 2003-07-31 Honda Motor Co Ltd 有機エレクトロルミネッセンス素子
JP4363050B2 (ja) 2002-01-31 2009-11-11 住友化学株式会社 有機エレクトロルミネッセンス素子
US6955773B2 (en) 2002-02-28 2005-10-18 E.I. Du Pont De Nemours And Company Polymer buffer layers and their use in light-emitting diodes
CN1639246A (zh) * 2002-03-01 2005-07-13 纳幕尔杜邦公司 包含添加剂的有机导电聚合物的印刷
JP2003264083A (ja) 2002-03-08 2003-09-19 Sharp Corp 有機ｌｅｄ素子とその製造方法
US6923881B2 (en) * 2002-05-27 2005-08-02 Fuji Photo Film Co., Ltd. Method for producing organic electroluminescent device and transfer material used therein
JP4288895B2 (ja) 2002-06-04 2009-07-01 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンスの製造方法
US20040004433A1 (en) * 2002-06-26 2004-01-08 3M Innovative Properties Company Buffer layers for organic electroluminescent devices and methods of manufacture and use
JP3606855B2 (ja) * 2002-06-28 2005-01-05 ドン ウン インターナショナル カンパニー リミテッド 炭素ナノ粒子の製造方法
US6963005B2 (en) 2002-08-15 2005-11-08 E. I. Du Pont De Nemours And Company Compounds comprising phosphorus-containing metal complexes
US7118836B2 (en) * 2002-08-22 2006-10-10 Agfa Gevaert Process for preparing a substantially transparent conductive layer configuration
US20040092700A1 (en) * 2002-08-23 2004-05-13 Che-Hsiung Hsu Methods for directly producing stable aqueous dispersions of electrically conducting polyanilines
US6977390B2 (en) * 2002-08-23 2005-12-20 Agfa Gevaert Layer configuration comprising an electron-blocking element
US7307276B2 (en) 2002-08-23 2007-12-11 Agfa-Gevaert Layer configuration comprising an electron-blocking element
JP2004082395A (ja) 2002-08-23 2004-03-18 Eamex Co 積層体形成方法及び積層体
US7033646B2 (en) 2002-08-29 2006-04-25 E. I. Du Pont De Nemours And Company High resistance polyaniline blend for use in high efficiency pixellated polymer electroluminescent devices
WO2004020444A1 (en) 2002-09-02 2004-03-11 Agfa-Gevaert New 3,4-alkylenedioxythiophenedioxide compounds and polymers comprising monomeric units thereof
JP4464277B2 (ja) 2002-09-24 2010-05-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法
US7317047B2 (en) * 2002-09-24 2008-01-08 E.I. Du Pont De Nemours And Company Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
DE60322923D1 (de) 2002-09-24 2008-09-25 Du Pont Wasserdispergierbare polythiophene hergestellt untäuren
KR101148285B1 (ko) 2002-09-24 2012-05-21 이 아이 듀폰 디 네모아 앤드 캄파니 전기적 응용을 위한 중합체성 산 콜로이드로 제조된수분산성 폴리아닐린
US7371336B2 (en) 2002-09-24 2008-05-13 E.I. Du Pont Nemours And Company Water dispersible polyanilines made with polymeric acid colloids for electronics applications
WO2004031192A1 (en) 2002-10-07 2004-04-15 Agfa-Gevaert 3,4-alkylenedioxythiophene compounds and polymers thereof
US6717358B1 (en) 2002-10-09 2004-04-06 Eastman Kodak Company Cascaded organic electroluminescent devices with improved voltage stability
US6793197B2 (en) * 2003-01-30 2004-09-21 Fisher Controls International, Inc. Butterfly valve
JP4851323B2 (ja) 2003-04-22 2012-01-11 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 高分子酸コロイドにより製造された水分散性ポリチオフェン
US7390438B2 (en) * 2003-04-22 2008-06-24 E.I. Du Pont De Nemours And Company Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids
WO2004105150A1 (en) 2003-05-19 2004-12-02 E.I. Dupont De Nemours And Company Hole transport composition
US20060135715A1 (en) 2003-06-27 2006-06-22 Zhen-Yu Yang Trifluorostyrene containing compounds, and their use in polymer electrolyte membranes
EP1507298A1 (en) 2003-08-14 2005-02-16 Sony International (Europe) GmbH Carbon nanotubes based solar cells
US8040042B2 (en) * 2003-09-08 2011-10-18 Sumitomo Metal Mining Co., Ltd. Transparent electroconductive layered structure, organic electroluminescent device using the same layered structure, method for producing the same layered structure, and method for producing the same device
US7618704B2 (en) * 2003-09-29 2009-11-17 E.I. Du Pont De Nemours And Company Spin-printing of electronic and display components
US20050069726A1 (en) 2003-09-30 2005-03-31 Douglas Elliot Paul Light emitting composite material and devices thereof
US7105237B2 (en) * 2003-10-01 2006-09-12 The University Of Connecticut Substituted thieno[3,4-B]thiophene polymers, method of making, and use thereof
JP4600284B2 (ja) 2003-10-28 2010-12-15 住友金属鉱山株式会社 透明導電積層体とその製造方法及び透明導電積層体を用いたデバイス
JP4402937B2 (ja) 2003-11-10 2010-01-20 株式会社日立製作所 ナノ粒子分散材料、ナノ粒子分散シート、及び、ナノ粒子分散積層シート
TW201219350A (en) * 2003-11-17 2012-05-16 Sumitomo Chemical Co Crosslinkable arylamine compounds
US20050209392A1 (en) * 2003-12-17 2005-09-22 Jiazhong Luo Polymer binders for flexible and transparent conductive coatings containing carbon nanotubes
US7960587B2 (en) 2004-02-19 2011-06-14 E.I. Du Pont De Nemours And Company Compositions comprising novel compounds and electronic devices made with such compositions
US7365230B2 (en) * 2004-02-20 2008-04-29 E.I. Du Pont De Nemours And Company Cross-linkable polymers and electronic devices made with such polymers
US7112369B2 (en) * 2004-03-02 2006-09-26 Bridgestone Corporation Nano-sized polymer-metal composites
US7338620B2 (en) * 2004-03-17 2008-03-04 E.I. Du Pont De Nemours And Company Water dispersible polydioxythiophenes with polymeric acid colloids and a water-miscible organic liquid
US7250461B2 (en) * 2004-03-17 2007-07-31 E. I. Du Pont De Nemours And Company Organic formulations of conductive polymers made with polymeric acid colloids for electronics applications, and methods for making such formulations
US7351358B2 (en) * 2004-03-17 2008-04-01 E.I. Du Pont De Nemours And Company Water dispersible polypyrroles made with polymeric acid colloids for electronics applications
WO2005090446A1 (en) * 2004-03-18 2005-09-29 Ormecon Gmbh A composition comprising a conductive polymer in colloidal form and carbon
US7455793B2 (en) * 2004-03-31 2008-11-25 E.I. Du Pont De Nemours And Company Non-aqueous dispersions comprising electrically doped conductive polymers and colloid-forming polymeric acids
US20050222333A1 (en) * 2004-03-31 2005-10-06 Che-Hsiung Hsu Aqueous electrically doped conductive polymers and polymeric acid colloids
US7354532B2 (en) * 2004-04-13 2008-04-08 E.I. Du Pont De Nemours And Company Compositions of electrically conductive polymers and non-polymeric fluorinated organic acids
US7378040B2 (en) * 2004-08-11 2008-05-27 Eikos, Inc. Method of forming fluoropolymer binders for carbon nanotube-based transparent conductive coatings
US20060051401A1 (en) 2004-09-07 2006-03-09 Board Of Regents, The University Of Texas System Controlled nanofiber seeding
KR20070102661A (ko) * 2004-09-24 2007-10-19 플렉스트로닉스, 인크 광기전 전지에서의 헤테로 원자를 갖는 위치 규칙적폴리(3-치환 티오펜)
US7211824B2 (en) * 2004-09-27 2007-05-01 Nitto Denko Corporation Organic semiconductor diode
US7388235B2 (en) * 2004-09-30 2008-06-17 The United States Of America As Represented By The Secretary Of The Navy High electron mobility transistors with Sb-based channels
KR100882503B1 (ko) 2004-10-06 2009-02-06 한국과학기술연구원 염료감응 태양전지용 고효율 대향전극 및 그 제조방법
US7569158B2 (en) * 2004-10-13 2009-08-04 Air Products And Chemicals, Inc. Aqueous dispersions of polythienothiophenes with fluorinated ion exchange polymers as dopants
EP1841773B1 (en) * 2004-12-30 2012-06-27 E.I. Du Pont De Nemours And Company Derivatized 3,4-alkylenedioxythiophene monomers, methods of making them, and use thereof
US7985490B2 (en) * 2005-02-14 2011-07-26 Samsung Mobile Display Co., Ltd. Composition of conducting polymer and organic opto-electronic device employing the same
US7645497B2 (en) 2005-06-02 2010-01-12 Eastman Kodak Company Multi-layer conductor with carbon nanotubes
US7593004B2 (en) * 2005-06-02 2009-09-22 Eastman Kodak Company Touchscreen with conductive layer comprising carbon nanotubes
US7727421B2 (en) * 2005-06-27 2010-06-01 E. I. Du Pont De Nemours And Company Dupont Displays Inc Electrically conductive polymer compositions
WO2007002682A2 (en) 2005-06-27 2007-01-04 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
WO2007002683A2 (en) * 2005-06-27 2007-01-04 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
WO2007002681A2 (en) 2005-06-27 2007-01-04 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
CN101208369B (zh) 2005-06-28 2013-03-27 E.I.内穆尔杜邦公司 高功函数透明导体
WO2007002740A2 (en) 2005-06-28 2007-01-04 E. I. Du Pont De Nemours And Company Buffer compositions
CN101616799A (zh) 2005-06-28 2009-12-30 E.I.内穆尔杜邦公司 双层阳极
US8088499B1 (en) 2005-10-28 2012-01-03 Agiltron, Inc. Optoelectronic device with nanoparticle embedded hole injection/transport layer
US8216680B2 (en) 2006-02-03 2012-07-10 E I Du Pont De Nemours And Company Transparent composite conductors having high work function
JP2009534831A (ja) 2006-04-18 2009-09-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 高エネルギーポテンシャル二重層組成物
US8153029B2 (en) * 2006-12-28 2012-04-10 E.I. Du Pont De Nemours And Company Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof
US20080251768A1 (en) * 2007-04-13 2008-10-16 Che-Hsiung Hsu Electrically conductive polymer compositions
US8241526B2 (en) * 2007-05-18 2012-08-14 E I Du Pont De Nemours And Company Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives
US20080283800A1 (en) 2007-05-18 2008-11-20 Che Hsiung Hsu Electrically conductive polymer compositions and films made therefrom
EP2173811A1 (en) 2007-07-27 2010-04-14 E. I. du Pont de Nemours and Company Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles

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CN102187747A (zh) * 2008-11-12 2011-09-14 柯达公司 聚合物导电供体和转移方法
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CN102395627A (zh) * 2009-04-24 2012-03-28 E.I.内穆尔杜邦公司 导电聚合物组合物和由其制得的膜
US8945427B2 (en) 2009-04-24 2015-02-03 E I Du Pont De Nemours And Company Electrically conductive polymer compositions and films made therefrom
CN102395627B (zh) * 2009-04-24 2015-04-01 E.I.内穆尔杜邦公司 导电聚合物组合物和由其制得的膜
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CA2500304A1 (en) 2004-04-08
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US20040124504A1 (en) 2004-07-01
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US20050070654A1 (en) 2005-03-31
TW200417592A (en) 2004-09-16
AU2003279011A1 (en) 2004-04-19
KR20050084574A (ko) 2005-08-26
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US8455865B2 (en) 2013-06-04
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WO2004029176A9 (en) 2007-10-11

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