CN105899547A - 包含聚(3,4-亚乙基二氧噻吩)和具有有限酸性的阴离子稳定剂的稳定成分 - Google Patents

包含聚(3,4-亚乙基二氧噻吩)和具有有限酸性的阴离子稳定剂的稳定成分 Download PDF

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CN105899547A
CN105899547A CN201480059304.3A CN201480059304A CN105899547A CN 105899547 A CN105899547 A CN 105899547A CN 201480059304 A CN201480059304 A CN 201480059304A CN 105899547 A CN105899547 A CN 105899547A
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pedot
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CN105899547B (zh
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C.纳瓦罗
W.斯马尔
M.蒙塔斯
E.克劳泰特
C.布罗乔恩
G.哈齐约安努
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Bordeaux, University of
Institute Of Technology Of Bordeaux
Centre National de la Recherche Scientifique CNRS
Arkema France SA
Universite de Bordeaux
Institut Polytechnique de Bordeaux
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Arkema France SA
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Abstract

本发明涉及聚(3,4‑亚乙基二氧噻吩)‑稳定的具有有限酸度的阴离子稳定剂的成分。

Description

包含聚(3,4-亚乙基二氧噻吩)和具有有限酸性的阴离子稳定剂的稳定成 分
技术领域
本发明涉及聚(3,4-亚乙基二氧噻吩)-具有有限酸度的离子稳定剂的稳定成分(合成物，组合物)。
背景技术
以缩写PEDOT已知的聚(3,4-亚乙基二氧噻吩)是20世纪80年代末在与AGFA集团合作的德国的Bayer AG的实验室中发现的聚合物。考虑到其良好的导电性和特别地考虑到其对氧化的稳定性及其透明度，其特别地用于有机电子应用中，尤其地用于光伏电池中，但是更通常地用于光电子应用中。
PEDOT是在常见溶剂中不可溶的聚合物。其通常与聚(苯乙烯-共聚-苯乙烯磺酸)(PSS)共聚物组合，这使得可将其分散在水中。PSS充当填料掺杂剂，形成由如下组成的胶体颗粒：连接至PEDOT的PSS链的缠结，其中富含PEDOT的核被富含PSS的冠覆盖。这些颗粒可以不同程度的导电性商购得到。PEDOT:PSS可经由常用方法例如旋转流延或通过喷墨印刷容易地以薄膜形式沉积。在许多光电子器件中，PEDOT:PSS层布置在由氧化铟锡(ITO)构成的电极层和活性有机材料的层之间。PEDOT:PSS提供电极的更好的机能，使粗糙的ITO表面光滑并因此限制短路，并且其保护活性有机层免于游离的铟和氧，赋予体系以延长的寿命。
遗憾地，PEDOT:PSS成分的根本性质有缺点。特别地，PEDOT:PSS的胶体分散体是高度酸性的并且是邻近层的劣化的潜在原因。为解决该问题，必需用另外的聚电解质替代非常酸性的PSS，而同时保持PEDOT:PSS的优点、特别地分散体的稳定性。
在多次测试后，申请人已经发现一类用作电荷掺杂剂的聚阴离子(Pan)稳定剂，其容许具有PEDOT的胶体分散体的非常良好的稳定性，而同时限制这些胶体分散体的酸性。所得到的膜易于制造并且同时具有良好的导电性和良好的机械性质。
发明内容
本发明涉及PEDOT:聚阴离子成分，其中所述聚阴离子包括对应于下式I的单体：
I：
A＝H、CH3
或芳基
R＝烷基或芳基
R1＝CF3、CH3、F
R'＝芳基
具体实施方式
通过在任选的离子或非离子共聚单体的存在下单体I的受控的自由基聚合或自由基聚合获得本发明的成分中使用的PAn。
任选地与I共聚的单体选自：乙烯基类、亚乙烯基类、二烯类、烯烃类、烯丙基类和(甲基)丙烯酸类单体。这些单体更特别地选自：乙烯基芳族单体，例如苯乙烯或取代的苯乙烯、特别地α-甲基苯乙烯，丙烯酸类单体，例如丙烯酸或其盐，丙烯酸烷基酯、丙烯酸环烷基酯或丙烯酸芳基酯，例如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸乙基己基酯或丙烯酸苯基酯，丙烯酸羟烷基酯例如丙烯酸2-羟基乙基酯，丙烯酸烷基醚酯例如丙烯酸2-甲氧基乙基酯，丙烯酸烷氧基聚亚烷基二醇酯或丙烯酸芳氧基聚亚烷基二醇酯，如丙烯酸甲氧基聚乙二醇酯、丙烯酸乙氧基聚乙二醇酯、丙烯酸甲氧基聚丙二醇酯、丙烯酸甲氧基聚乙二醇-聚丙二醇酯或它们的混合物，丙烯酸氨基烷基酯，如丙烯酸2-(二甲基氨基)乙基酯(DAMEA)，氟化丙烯酸酯，丙烯酸甲硅烷基酯，含磷的丙烯酸酯例如亚烷基二醇磷酸酯丙烯酸酯，丙烯酸缩水甘油酯或丙烯酸二环戊烯基氧乙基酯，甲基丙烯酸类单体例如甲基丙烯酸或其盐，甲基丙烯酸烷基酯、甲基丙烯酸环烷基酯、甲基丙烯酸烯基酯或甲基丙烯酸芳基酯，如甲基丙烯酸甲酯(MMA)、甲基丙烯酸月桂基酯、甲基丙烯酸环己基酯、甲基丙烯酸烯丙基酯、甲基丙烯酸苯基酯或甲基丙烯酸萘基酯，甲基丙烯酸羟烷基酯例如甲基丙烯酸2-羟基乙基酯或甲基丙烯酸2-羟基丙基酯，甲基丙烯酸烷基醚酯例如甲基丙烯酸2-乙氧基乙基酯，甲基丙烯酸烷氧基聚亚烷基二醇酯或甲基丙烯酸芳氧基聚亚烷基二醇酯例如甲基丙烯酸甲氧基聚乙二醇酯、甲基丙烯酸乙氧基聚乙二醇酯、甲基丙烯酸甲氧基聚丙二醇酯、甲基丙烯酸甲氧基聚乙二醇-聚丙二醇酯或它们的混合物，甲基丙烯酸氨基烷基酯例如甲基丙烯酸2-(二甲基氨基)乙基酯(DAMEMA)，氟化甲基丙烯酸酯例如甲基丙烯酸2,2,2-三氟乙基酯，甲基丙烯酸甲硅烷基酯例如3-甲基丙烯酰基丙基三甲基硅烷，含磷的甲基丙烯酸酯例如亚烷基二醇磷酸酯甲基丙烯酸酯，甲基丙烯酸羟乙基咪唑啉酮酯，甲基丙烯酸羟乙基亚乙基脲酯，甲基丙烯酸2-(2-氧代-咪唑烷基)乙基酯，丙烯腈，丙烯酰胺或取代的丙烯酰胺，4-丙烯酰基吗啉，N-羟甲基丙烯酰胺，甲基丙烯酰胺或取代的甲基丙烯酰胺，N-羟甲基甲基丙烯酰胺，甲基丙烯酰氨基丙基三甲基氯化铵(MAPTAC)，甲基丙烯酸缩水甘油酯或甲基丙烯酸二环戊烯基氧乙基酯，衣康酸、马来酸或其盐，马来酸酐，马来酸或半马来酸烷基或烷氧基-聚亚烷基二醇或芳氧基-聚亚烷基二醇酯，乙烯基吡啶，乙烯基吡咯烷酮，(烷氧基)聚(亚烷基二醇)乙烯基醚或二乙烯基醚，例如甲氧基聚(乙二醇)乙烯基醚，聚(乙二醇)二乙烯基醚，烯烃类单体，其中可提及乙烯、丁烯、己烯和1-辛烯，二烯类单体，包括丁二烯，异戊二烯，和氟烯烃单体，以及亚乙烯基类单体(其中可提到偏二氟乙烯)，或这些单体的组合。
PAn的聚合优选地通过受控的自由基聚合进行，无论是经由氮氧自由基(氮氧化物)、RAFT(可逆加成和断裂转移)或ATRP(原子转移自由基聚合)。
根据本发明的第一方面，以得自稳定自由基(1)的烷氧基胺为起始进行受控的自由基聚合。
其中基团RL具有大于15.0342g/mol的摩尔质量。基团RL可为卤素原子例如氯、溴或碘，线性的、支化的或环状的、饱和的或不饱和的基于烃的基团例如烷基或苯基基团，或酯基团-COOR或烷氧基-OR，或磷酸酯基团-PO(OR)2，条件是其具有大于15.0342的摩尔质量。认为单价基团RL在相对于氮氧化物自由基的氮原子的β位上。式(1)中的碳原子和氮原子的剩余化合价位置可连接于多种基团例如氢原子；基于烃的基团例如烷基、芳基或芳基烷基基团，其包括1-10个碳原子。式(1)中的碳原子和氮原子不排除经由二价基团连接在一起，以形成环。然而，优选地，式(1)的碳原子和氮原子的剩余化合价位置连接至单价基团。优选地，基团RL具有大于30g/mol的摩尔质量。基团RL可具有例如40-450g/mol的摩尔质量。举例来说，基团RL可为包括磷酰基的基团，所述基团RL可由下式表示：
其中可相同或不同的R3和R4可选自烷基、环烷基、烷氧基、芳氧基、芳基、芳烷氧基、全氟烷基和芳烷基基团，并且可包含1-20个碳原子。R3和/或R4还可为卤素原子例如氯或溴或氟或碘原子。基团RL还可包含至少一个芳环，如对于苯基基团或萘基基团，后者可为取代的，例如被包括1-4个碳原子的烷基基团取代的。
更特别地，得自下列稳定的自由基的烷氧基胺是优选的：
-N-叔丁基-1-苯基-2-甲基丙基氮氧自由基，
-N-叔丁基-1-(2-萘基)-2-甲基丙基氮氧自由基，
-N-叔丁基-1-二乙基膦酰基-2,2-二甲基丙基氮氧自由基，
-N-叔丁基-1-二苄基膦酰基-2,2-二甲基丙基氮氧自由基，
-N-苯基-1-二乙基膦酰基-2,2-二甲基丙基氮氧自由基，
-N-苯基-1-二乙基膦酰基-1-甲基乙基氮氧自由基，
-N-(1-苯基-2-甲基丙基)-1-二乙基膦酰基-1-甲基乙基氮氧自由基，
-4-氧代-2,2,6,6-四甲基-1-哌啶基氧，
-2,4,6-三-叔丁基苯氧基。
用于受控的自由基聚合中的烷氧基胺必须容许单体序列的良好控制。因此，它们不是全部容许某些单体的良好控制。例如，得自TEMPO的烷氧基胺使得可控制仅有限数量的单体，并且对于得自2,2,5-三甲基-4-苯基-3-氮杂己烷3-氮氧自由基(TIPNO)的烷氧基胺也是这种情况。另一方面，得自对应于式(1)的氮氧自由基的其它烷氧基胺，特别地得自对应于式(2)的氮氧自由基的那些和甚至更特别地得自N-叔丁基-1-二乙基膦酰基-2,2-二甲基丙基氮氧自由基的那些，使得可将这些单体的受控自由基聚合拓宽至大量的单体。
另外，烷氧基胺的打开温度也对经济因素具有影响。优选使用低温以最小化工业困难。相比于得自TEMPO或2,2,5-三甲基-4-苯基-3-氮杂己烷3-氮氧自由基(TIPNO)的烷氧基胺，得自对应于式(1)的氮氧自由基的烷氧基胺、特别地得自对应于式(2)的氮氧自由基的那些和甚至更特别地得自N-叔丁基-1-二乙基膦酰基-2,2-二甲基丙基氮氧自由基的那些将因此是优选的。
根据本发明的第二个形式，经由RAFT进行所述受控的自由基聚合，并且更特别地使用对应于下式II的RAFT试剂：
II：
其中R表示包括1-22个碳原子、优选地10-18个碳原子和更优选地12个碳原子的烷基。
作为本发明主题的PEDOT:PAn成分可用于分散纳米填料例如碳纳米管(无论其为单壁或多壁的)、石墨烯或银纳米纱。用这些成分获得的膜具有良好的透明度和良好的导电性。本发明的成分可还包含添加剂、特别地乙二醇。
实施例1：
使用2-(十二烷基-硫烷基-硫代羰基-硫烷基)-2-甲基丙酸(2-(dodecyl-sulfanyl-thiocarbonyl-sulfanyl)-2-methylpropionic acid)经由RAFT的钾4-苯乙烯磺酰基(三氟甲磺酰基)酰亚胺的聚合：
称为STFSIK的单体钾4-苯乙烯磺酰基(三氟甲磺酰基)酰亚胺的合成根据文献进行并且描述于文章R.Meziane等,Electrochimica Acta,2011,57,14-19中。
RAFT试剂(2-(十二烷基-硫烷基-硫代羰基-硫烷基)-2-甲基丙酸)根据文献合成并且描述于文章J.T.Lai等，Macromolecules，2002，35，6754-6756中。
将2g(5.66mmol)的钾4-苯乙烯磺酰基(三氟甲磺酰基)酰亚胺、36.4mg(0.1mmol)的2-(十二烷基-硫烷基-硫代羰基-硫烷基)-2-甲基丙酸、3.28mg(0.02mmol)的AIBN(偶氮二异丁腈)和4ml的二甲基甲酰胺(DMF)放置在干燥的Schlenk管中。然后使所述Schlenk管惰性并且放置在65℃下的油浴中。在总的转化(24小时)之后，将Schlenk管浸在液氮中。通过用醚沉淀、然后过滤，将聚合物PSTFSIK(钾聚(4-苯乙烯磺酰基(三氟甲磺酰基)酰亚胺)洗涤两次。然后在60℃下将所述聚合物在真空下在烘箱中干燥。通过质子NMR(图1)和19-氟NMR(图2)证实所述聚合物的结构。
采用聚苯乙烯标准物通过SEC测量的数均分子量为20 000g/mol，并且多分散指数为1.1。
实施例2：在PSTFSIK存在下EDOT的聚合：
将溶解于150ml去离子水中的1.65g(Mn 20 000g/mol)的PSFTSIK、0.3ml(2.81mmol)的EDOT(Sigma-Aldrich)在搅拌下置于单颈圆底烧瓶中。然后引入过硫酸铵(640mg，2.81mmol)和氯化铁(136mg，0.84mmol)的混合物。在25℃下在氮气气氛下剧烈搅拌反应混合物48小时。这得到深蓝色的分散体。通过如下洗涤所得的PEDOT和PSTFSIK的分散体：在去离子水存在下使用再生纤维素微孔膜NMWL:100 000(分子量截止值)超滤，以除去未连接至PEDOT的PSTFSIK和源自氧化剂的盐。最后的固体产率为85％。通过旋涂用该分散体制备膜，并且使其经历AFM成像。图3显示范围为40-50nm的粒度。
将实施例1中制备的PEDOT-聚苯乙烯-共聚-聚苯乙烯磺酸盐乳胶与商业乳胶(PEDOT-聚苯乙烯-共聚-聚苯乙烯磺酸盐)比较。
将这些产物分散在去离子水(1质量％)中并且使用IKA T18Ultra-turrax共混机以多种速率(15 500、20 000、24 000rpm)经受剪切，对于各速率经受剪切5分钟。
在这些条件下，无论对于商业乳胶或作为本发明主题的乳胶，不可能观察到丝毫的(最轻微的)团聚体，显示这两种乳胶的非常良好的稳定性。
实施例3：单壁碳纳米管在实施例2的分散体中的分散：
借助实施例2的分散体用强力超声激发若干分钟，将来自Arkema公司的多壁碳纳米管分散在水中。通过超速离心除去残余聚集体。在包含0.26重量％的PEDOT:PSTFSIK对的水溶液中，对于至多0.15重量％的碳纳米管浓度，观察到稳定的分散体。
实施例4：本体PEDOT:PSTFSIK对的导电性
经由“4-探针”方法对1mm厚和13mm直径的盘形式的压制的PEDOT:PSTFSIK样品测量PEDOT:PSTFSIK的样品的电导率。使用10吨液压机获得所述盘。在多种合成实验条件下制备的这些盘的质量电导率报告于表1中。
IPA：异丙醇
EG：乙二醇
APS：过硫酸铵
Fe(OTs)3：甲苯磺酸铁
当EDOT和STFSIK的摩尔比为0.6:1时，使用以1:0.3比率的APS/FeCl3氧化对得到最好的电导率。当在水/异丙醇混合物中或在水/乙二醇混合物中进行合成时，没有观察到电导率(导电性)。
实施例5：PEDOT:PSTFSIK对的导电性和碳纳米管在PEDOT:PSTFSIK分散体中的分散体的导电性
通过将具有10质量％的乙二醇的PEDOT:PSTFSIK分散体喷涂在放置于加热至100℃的热板上的玻璃板上，制备PEDOT:PSTFSIK的薄膜。经由4探针技术测量电阻并且使用Shimadzu UV-Vis-NIR UV-3600分光光度计在550nm处测量透射率。
以相同的方式，由如实施例3中制备的包含碳纳米管的分散体制造薄膜并且测量导电性和透射率。
在图4中得到曲线图。
特别地注意到，相较于来自Clevios公司的PEDOT:PSS PH1000(记作PEDOT:PSS)，包含碳纳米管(CNT)的配制物的令人满意的行为。

Claims (11)

1.PEDOT：聚阴离子成分，其中所述聚阴离子包含对应于下式I的单体：
I：
A＝H、CH3
或芳基
R＝烷基或芳基
R1＝CF3、CH3、F
R'＝芳基。
2.如权利要求1所述的成分，其中所述聚阴离子是通过采用氮氧自由基的受控的自由基聚合而聚合的。
3.如权利要求2所述的成分，其中所述氮氧自由基是N-叔丁基-1-二乙基膦酰基-2,2-二甲基丙基氮氧自由基。
4.如权利要求1所述的成分，其中所述聚阴离子是通过RAFT类型的受控的自由基聚合而聚合的。
5.如权利要求4所述的成分，其中RAFT试剂对应于下式II：
II：
其中R表示包含1-22个碳原子的烷基。
6.如权利要求1所述的成分，其还包含添加剂。
7.如权利要求6所述的成分，其中所述添加剂为乙二醇。
8.导电透明膜，其由如权利要求1-7之一所述的成分获得。
9.如权利要求1-7之一所述的成分用于分散纳米填料的用途。
10.如权利要求9所述的用途，其中所述纳米填料由碳纳米管组成。
11.导电透明膜，其由如权利要求1-7之一所述的成分和碳纳米管获得。
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