CN101821815A - 通过喷墨印刷制备导电涂层的方法 - Google Patents
通过喷墨印刷制备导电涂层的方法 Download PDFInfo
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- CN101821815A CN101821815A CN200880104637A CN200880104637A CN101821815A CN 101821815 A CN101821815 A CN 101821815A CN 200880104637 A CN200880104637 A CN 200880104637A CN 200880104637 A CN200880104637 A CN 200880104637A CN 101821815 A CN101821815 A CN 101821815A
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明涉及一种通过喷墨印刷制备包含分散体或溶液的导电涂层的新方法,该分散体或溶液包含至少一种任选取代的聚噻吩、至少一种聚阴离子、水、至少一种溶剂和至少一种碱性添加剂,此方法的特征在于利用至少一种碱性添加剂将含水的分散体或溶液的pH值调整到2-10的范围内;本发明还涉及导电涂层及其应用。
Description
本发明涉及通过喷墨印刷制备导电涂层的新方法、导电涂层及其用途。
利用包含聚亚烷基二氧噻吩(polyalkylenedioxythiophenes)、尤其是聚3,4-亚乙基二氧噻吩的分散体或溶液制备导电和/或防静电涂层是公知的方法,例如EP0440957。
EP1112673公开了一种利用喷墨印刷由包含聚亚烷基二氧噻吩的分散体制备导体线路的方法。
但是,实践中已经发现包含聚噻吩、尤其是聚亚烷基二氧噻吩的分散体或溶液,即使经过预先过滤,也容易堵塞喷墨印刷机的印刷头,因而不能长时间印刷。
因此需要有一种制备导电涂层的喷墨印刷方法,其能避免被所使用的分散体或溶液堵塞印刷头。
因此本发明的一个目的就是提供这样一种方法。
我们惊奇的发现在印刷之前对分散体或溶液进行中和可以防止堵塞喷墨印刷机的印刷头。
因此本发明提供一种通过喷墨印刷制备包含分散体或溶液的导电涂层的方法,该分散体或溶液包含至少一种任选取代的聚噻吩、至少一种聚阴离子、水、至少一种溶剂和至少一种碱性添加剂,所述方法的特征在于利用至少一种碱性添加剂将含水的分散体或溶液的pH值调整到2-10的范围内。
在本发明中,任选取代的聚噻吩可以优选是包含通式(I)重复单元的任选取代的聚噻吩,
其中
A是任选取代的C1-C5亚烷基,优选为任选取代的亚乙基或亚丙基,
R是直链或支化的任选取代的C1-C18烷基,优选为直链或支化的任选取代的C1-C14烷基,任选取代的C5-C12环烷基,任选取代的C6-C14芳基,任选取代的C7-C18芳烷基,任选取代的C1-C4羟基烷基或羟基,
x是0-8的整数,优选为0、1或2,更优选0或1,和
在多个R与A键接的情况下,这些R基团可以相同或不同。
通式(I)应该理解为取代基R可以与亚烷基A键接x次。
在本发明中,含水的分散体或溶液也可以包含两种或更多种的含有通式(I)重复单元的不同聚噻吩的混合物。
在优选实施方案中,含有通式(I)重复单元的聚噻吩是包含通式(Ia)重复单元的聚噻吩,
其中,R和x的定义如前所述。
在另一个优选实施方案中,含有通式(I)重复单元的聚噻吩是包含通式(Iaa)重复单元的聚噻吩。
在本发明中,前缀“聚”的意思是在聚噻吩中存在多于一个的相同或不同的重复单元。聚噻吩包含总共n个通式(I)的重复单元,其中n可以为2-2000范围内的整数,优选为2-100。通式(I)的重复单元可以各自在聚噻吩中是相同或不同的。优选在每种情况下包含通式(I)的相同重复单元的聚噻吩。
在端基上,聚噻吩优选为各自带有氢。
在一个特别优的选实施方案中,含有通式(I)重复单元的聚噻吩是聚(3,4-亚乙基二氧噻吩),即从式(Iaa)的重复单元形成的均聚噻吩。
在本发明中,C1-C5亚烷基A为亚甲基、亚乙基、亚正丙基、亚正丁基或亚正戊基。在本发明中,C1-C18烷基代表直链或支化的C1-C18烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基、正己基、正庚基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十六烷基或正十八烷基,C5-C12环烷基代表C5-C12环烷基,例如环戊基、环己基、环庚基、环辛基、环壬基或环癸基,C5-C14芳基代表C5-C14芳基例如苯基或萘基,C7-C18芳烷基代表C7-C18芳烷基例如苄基、邻苯基、间甲苯基、对甲苯基、2,3-、2,4-、2,5-、2,6-、3,4-、3,5-二甲苯基或均三甲苯基。上面所述内容用来举例阐述本发明,而不应认为仅限于此。
有用的C1-C5亚烷基A的任选其它取代基包括各种有机基团,例如烷基、环烷基、芳基、卤素、醚、硫醚、二硫化物、亚砜、砜、磺酸盐、氨基、醛、酮基、羧酸酯、羧酸、碳酸盐、羧酸盐、氰基、烷基硅烷和烷氧基硅烷基团以及碳酰胺基团。
上面所述的分散体或溶液,优选包含聚3,4-亚烷基二氧噻吩,例如,可以通过与EP440957中所述方法类似的方法来制得。有用的氧化剂和溶剂也同样包括EP440957中所列举的那些。例如,粒子的直径分布可以通过高压均化确定。溶胀状态的粒径优选为小于1μm,更优选为小于100nm。
用于生产通式(I)聚噻吩和其衍生物的单体前体的制备方法是本领域技术人员所公知的,例如在L.Groenendaal,F.Jonas,D.Freitag,H.Pielartzik和J.R.Reynolds等人2000年发表在Adv.Mater.第12卷第481-494页的文章及其引用文献中已经公开。
导电聚噻吩可以是不带电荷或是阳离子性的。在优选实施方案中,它们是阳离子性的,这里的“阳离子性”仅指的是停留在聚合物或聚噻吩主链上的电荷。根据R基团上的取代基,聚合物或聚噻吩可以在结构单元中携带正电荷和负电荷,在这种情况下正电荷存在于聚合物或聚噻吩的主链上,而负电荷可以存在于被磺酸盐基或羧酸盐基取代的R基团上。这种情况下,聚合物或聚噻吩主链上的正电荷可以部分或全部被可存在于R基团上的阴离子基团饱和。总体来看,这些情况下的聚噻吩可以是阳离子性、不带电荷或甚至阴离子性的。但是在本发明内容中,因为在聚合物或聚噻吩主链上的正电荷是至关重要的,这里的聚噻吩都被认为是阳离子性聚噻吩。
由于正电荷的准确数目和位置无法明确说明,所以在通式中并没有显示出正电荷。但是正电荷的数目至少为1,最多为n,其中n是聚噻吩中所有重复单元(相同或不同)的总数。在下面的内容中,阳离子性聚噻吩也被称作聚阳离子。
为了补偿正电荷,这种补偿没有被磺酸盐基或羧酸盐基任选取代并进而带负电荷的R基团实现,阳离子性聚合物或聚噻吩需要阴离子作为抗衡离子。
有用的抗衡离子优选包括聚合物阴离子,在下面的内容中也被称作聚阴离子。
合适的聚阴离子包括例如聚羧酸如聚丙烯酸、聚甲基丙烯酸或聚马来酸的阴离子,或聚磺酸如聚苯乙烯磺酸和聚乙烯基磺酸的阴离子。这些聚羧酸和聚磺酸也可以是乙烯基羧酸和乙烯基磺酸与其它可聚合单体(如丙烯酸酯和苯乙烯)的共聚物。
一种特别优选的聚阴离子是聚苯乙烯磺酸(PPS)的阴离子。
用来作为聚阴离子的聚酸的分子量优选为1000-2,000,000,更优选为2000-500,000。聚酸或它们的碱金属盐在商业上是可以获得的,例如聚苯乙烯磺酸和聚丙烯酸,或可以通过公知方法制备(例如参见Houben Weyl,Methoden der organischen Chemie的《有机化学方法》,卷E20。Makromolekulare Stoffe的《大分子物质》,第二部分第1141页起,1987)。
包含阴离子作为抗衡离子以提供电荷补偿的阳离子性聚噻吩在本技术领域也被称为聚噻吩/(聚)阴离子复合物。
在含水的分散体或溶液中,任选取代的聚噻吩的固含量、尤其具有通式(I)重复单元的任选取代的聚噻吩的固含量为0.05-3.0重量%,优选为0.1-1.0重量%。
在本发明的另一个优选实施方案中,含水的分散体或溶液包含3,4-聚(亚乙基二氧噻吩)和聚苯乙烯磺酸盐。
本发明中合适的溶剂为至少部分能与水混溶的溶剂,例如醇,例如甲醇、乙醇、正丙醇、异丙醇、丁醇或辛醇;二醇或二醇醚,例如乙二醇、二甘醇、丙烷-1,2-二醇、丙烷-1,3-二醇或双丙甘醇二甲醚;或酮,例如丙酮或甲基乙基酮。
溶剂的含量为0-90重量%,优选5-60重量%。在本发明内容中,优先考虑使用在标准压力下沸点低于100℃的溶剂与沸点高于100℃的溶剂的混合物。
分散体或溶液可以另外包含至少一种聚合物粘合剂。
合适的粘合剂是聚合物有机粘合剂,例如聚乙烯醇、聚乙烯基吡咯烷酮、聚氯乙烯、聚乙酸乙烯酯、聚丁酸乙烯酯、聚丙烯酸酯、聚丙烯酰胺、聚甲基丙烯酸酯、聚甲基丙烯酰胺、聚丙烯腈、苯乙烯/丙烯酸酯共聚物、乙酸乙烯酯/丙烯酸酯共聚物、乙烯/乙酸乙烯酯共聚物、聚丁二烯、聚异戊二烯、聚苯乙烯、聚醚、聚酯、聚碳酸酯、聚氨酯、聚酰胺、聚酰亚胺、聚砜、三聚氰胺甲醛树脂、环氧树脂、硅树脂或纤维素。
聚合物粘合剂的固含量为0-3重量%,优选为0-1重量%。
在本发明内容中,分散体或溶液还可以另外包含至少一种染料和/或至少一种表面活性剂。染料的含量可以是0-5重量%,优选为0-0.5重量%。有用的染料包括例如偶氮染料、吖嗪染料、蒽醌染料、吖啶染料、花青染料、靛蓝染料、硝基染料、噁嗪染料、酞菁染料、邻苯二甲酸染料、聚甲炔染料、噻嗪染料或三芳基甲烷染料。表面活性剂的含量为0-5重量%,优选为0.01-0.5重量%。表面活性剂可以是阴离子性的、阳离子性的、非离子性的或两性的表面活性剂,聚电解质或嵌段共聚物。
分散体或溶液还可以另外包含助粘剂,例如有机官能硅烷或其水解物,例如3-缩水甘油基氧丙基三烷氧基硅烷、3-氨基丙基三乙氧基硅烷、3-巯基丙基三甲氧基硅烷、3-甲基丙烯酰基丙氧基三甲氧基硅烷、乙烯基三甲氧基硅烷或辛基三乙氧基硅烷。
考虑到上述其他成分,分散体或溶液中的水含量通过下式计算:
水含量(重量%)=100-其他成分之和(重量%)。
在发明内容中,使用的碱性添加剂可以是碱金属氢氧化物如氢氧化锂、氢氧化钠、氢氧化钾,碱金属碳酸盐或碱金属碳酸氢盐例如碳酸锂、碳酸钠、碳酸钾或碳酸铯,碱土金属氢氧化物例如氢氧化镁、氢氧化钙、氢氧化钡或氢氧化锶,碱土金属碳酸盐例如碳酸镁、碳酸钙或碳酸钡,氨,脂族烷基胺例如带有任选取代的C1-C20烷基的单-、二-或三-烷基胺,例如甲胺、二甲胺、三甲胺、乙胺、二乙胺、三乙胺、乙醇胺、二甲基乙醇胺或三乙醇胺。
碱性添加剂优选以溶液的形式使用,例如在水和/或醇中,用来中和分散体或溶液。合适的醇是例如甲醇、乙醇、正丙醇、异丙醇、丁醇或辛醇,二醇或二醇醚,例如乙二醇、二甘醇、丙烷-1,2-二醇或丙烷-1,3-二醇。
在本发明的方法中,将碱性添加剂加入到分散体或溶液中并同时用pH计监测分散体或溶液的pH值,优选在添加过程中进行搅拌。在添加完碱性添加剂后,分散体或溶液的pH值应该在2-10的范围内,优选为4-9,更优选为6-8。
碱性添加剂的用量根据中和之前分散体或溶液中的酸含量自动调整。按每摩尔要中和的酸计,需要添加0.05-1.0摩尔、优选为0.1-1摩尔的碱性添加剂。
在添加完碱性添加剂之后,在印刷前过滤分散体或溶液。合适的过滤器是例如聚丙烯过滤器,其孔径小于1μm,优选为小于0.5μm,更优选为小于0.2μm。过滤可以在标准压力或最高到10巴的高压下进行。
优选将溶液多次通过过滤器,例如通过泵输送使其循环通过过滤器。
这样得到的分散体或溶液的粘度为2-2000mPas,优选为5-100mPas,更优选为7-25mPas。
碱性添加剂除了能够提高分散体或溶液的稳定性之外,还具有减小分散体或溶液的腐蚀性的积极作用。因此能够避免或至少减缓腐蚀,尤其是对喷墨印刷机的印刷头的腐蚀。
添加碱性添加剂的另一个积极作用在于使得分散体所施用的基质不被腐蚀。特别地,导电透明无机层(“透明导电氧化物”,简称TCO),例如氧化铟锡(ITO)或掺氟的氧化锌(AZO)层,在与酸性溶液接触时容易分解。这导致这些层的上部被金属离子污染,这对整体结构的功能是不利的。对于由硅组成的活性矩阵基质也是如此,这些结构用于显示器中的电子放大电路中。通过提高pH值降低了基质被蚀刻的概率。
分散体或溶液可以用商用的喷墨印刷机印刷,例如Dimatix公司的印刷机。例如,在期刊ChipHeft(8,104-112页,1994)中公开了合适的喷墨通过按需滴墨的方法与压电印刷头一起工作,或者通过气泡喷墨方法进行。也可以使用通过连续喷墨方法工作的喷墨印刷机。
本发明进一步提供平坦的或结构化的导电涂层,这些导电涂层是由本发明方法制备的。
根据本发明制备的导电涂层特别适合在聚合物例如聚酯薄膜上制备印刷电路,用来制备基于有机半导体的晶体管、场效应管或集成电路。例如,在文章“具有百纳米基以下分辨率的无石印的、自排列的喷墨印刷(Lithography-Free,self-alighed Inkjet Printing withSub-Hundred-Nanometer Resolution)”(C.W.Sele等,Adv.Mater.2005,17,997-1001)中详细叙述了通过喷墨方法制备有机场效应晶体管的方法。
此外,根据本发明方法制备的导电涂层可以用于制备透明电极或电洞注入层,后者用于无机或有机场致发光灯或显示器。例如,通过喷墨方法制备由聚合物发光二极管构成的显示器的方法在文章“聚合物发光显示器的精确喷墨印刷(Precision ink jet printing of polymer light emittingdisplays)”(J.F.Dijksman等,J.Mater.Chem.2007,17,511-522)中有详细叙述。
实施例
对比例1
在一个10升烧杯中先加入固含量为1.6%的2560g的PH 510(H.C Starck GmbH公司)。在用框式搅拌器搅拌的同时,依次加入下述物质:
100g的二甲基亚砜
8.0g的Dynol 604(来自Air Products公司)
400g的二甘醇
2180g的水
1000g的乙醇
2.0g的正辛醇,和
2.0g的Triton X 100(来自Aldrich公司)。
随后搅拌分散体30分钟,然后用L&Z公司的孔径0.2μm的滤芯以14升/小时的处理量过滤6小时。
实施例1:
按照对比例1中的方法制备分散体,区别在于在过滤前,通过在搅拌下加入50%的二甲基乙醇胺水溶液使得分散体的pH值调整到7。在调整好pH值后,按照对比例1中的方法过滤分散体。
实施例2:
将根据对比例1和实施例1两种情况下得到的分散体各1.5ml分别加入到Dimatix DMP 2831喷墨印刷机的墨盒中。将墨盒放置在印刷机中,印刷出2×2cm2的区域。重复进行这种印刷,直到此区域不再被完全填充或强度损失明显减小。印刷在175μm厚的聚酯膜或在纸上进行。
表1
实施例 | 全面积印刷的数目 |
对比例 | 5 |
实施例1 | 20 |
如表1中所示的结果,与使用对比例的分散体相比,使用实施例1制备的分散体能得到更好的印刷结果。
Claims (10)
1.一种通过喷墨印刷制备包含分散体或溶液的导电涂层的方法,该分散体或溶液包含至少一种任选取代的聚噻吩、至少一种聚阴离子、水、至少一种溶剂和至少一种碱性添加剂,此方法的特征在于利用至少一种碱性添加剂将含水的分散体或溶液的pH值调整到2-10的范围内。
4.如权利要求1-3中至少一个权利要求所述的方法,其特征在于含水的分散体或溶液包含3,4-聚(亚乙基二氧噻吩)和聚苯乙烯磺酸盐。
5.如权利要求1-4中至少一个权利要求所述的方法,其特征在于至少一种碱性添加剂选自碱金属氢氧化物、碱金属碳酸盐、碱土金属氢氧化物、碱土金属碳酸盐、氨或脂族烷基胺。
6.如权利要求1-5中至少一个权利要求所述的方法,其特征在于含水的分散体或溶液的pH值通过至少一种碱性添加剂调整到6-8的范围内。
7.如权利要求1-6中至少一个权利要求所述的方法,其特征在于含水的分散体或溶液另外包含至少一种聚合物粘合剂。
8.如权利要求1-7中至少一个权利要求所述的方法,其特征在于含水的分散体或溶液另外包含至少一种表面活性剂和/或至少一种染料。
9.通过权利要求1-8中至少一个权利要求所述的方法制备的导电涂层。
10.如权利要求9中的导电涂层在晶体管、场效应晶体管、集成电路、透明电极或者无机或有机场致发光阵列中的用途。
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PCT/EP2008/059875 WO2009027164A1 (en) | 2007-08-29 | 2008-07-28 | Production of conductive coatings by means of inkjet printing |
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CN105074947A (zh) * | 2013-03-29 | 2015-11-18 | 贺利氏德国有限两合公司 | 作为pedot/pss分散体中的增粘剂添加剂的非极性溶剂 |
CN106459639A (zh) * | 2014-06-13 | 2017-02-22 | 株式会社Lg化学 | 导电聚合墨水组合物 |
CN106459638A (zh) * | 2014-05-27 | 2017-02-22 | 株式会社Lg化学 | 导电聚合物油墨组合物 |
CN106796377A (zh) * | 2014-10-27 | 2017-05-31 | 株式会社Lg化学 | 包括经中和的导电聚合物透明电极的聚合物分散液晶元件及其生产方法 |
CN108140441A (zh) * | 2015-10-20 | 2018-06-08 | 索尔维公司 | 用于形成透明导体的组合物以及由其制成的透明导体 |
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FR2951402B1 (fr) * | 2009-10-19 | 2011-12-09 | Polypore | Procede d'impression par jet d'encre pour encre fonctionnelle sur tout support |
JP5640654B2 (ja) * | 2010-10-29 | 2014-12-17 | 岩崎通信機株式会社 | 導電膜用塗料の製造方法および透明導電性フィルム |
JP5789479B2 (ja) * | 2011-10-26 | 2015-10-07 | 信越ポリマー株式会社 | 有機エレクトロルミネッセンス素子 |
JP6182884B2 (ja) * | 2013-02-05 | 2017-08-23 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2015190727A1 (ko) * | 2014-06-13 | 2015-12-17 | 주식회사 엘지화학 | 전도성 고분자 잉크 조성물 |
FR3083236B1 (fr) * | 2018-06-29 | 2020-12-04 | Dracula Tech | Composition de polymere conducteur et son procede de fabrication |
KR102103860B1 (ko) * | 2019-10-18 | 2020-04-24 | 에스케이씨하이테크앤마케팅(주) | 전도성 코팅액 조성물 및 이로부터 제조된 전도층을 포함하는 플렉서블 디스플레이용 투명 전도성 필름 |
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DE59010247D1 (de) * | 1990-02-08 | 1996-05-02 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
DE19841804A1 (de) | 1998-09-12 | 2000-03-16 | Bayer Ag | Leiterbahnen aus Polyalkylendioxythiophen |
US6340496B1 (en) * | 1999-05-20 | 2002-01-22 | Agfa-Gevaert | Method for patterning a layer of conductive polymers |
US6955772B2 (en) * | 2001-03-29 | 2005-10-18 | Agfa-Gevaert | Aqueous composition containing a polymer or copolymer of a 3,4-dialkoxythiophene and a non-newtonian binder |
DE10111790A1 (de) * | 2001-03-12 | 2002-09-26 | Bayer Ag | Neue Polythiophen-Dispersionen |
JP3855167B2 (ja) * | 2001-03-29 | 2006-12-06 | アグフア−ゲヴエルト,ナームローゼ・フエンノートシヤツプ | 3,4−ジアルコキシチオフェンのポリマーもしくはコポリマー及び非−ニュートニアン結合剤を含有する水性組成物。 |
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- 2007-08-29 DE DE102007041039A patent/DE102007041039A1/de not_active Withdrawn
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- 2008-07-28 KR KR1020137004765A patent/KR20130038398A/ko not_active Application Discontinuation
- 2008-07-28 JP JP2010522285A patent/JP2010537019A/ja active Pending
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TW200929264A (en) | 2009-07-01 |
CA2697472A1 (en) | 2009-03-05 |
KR20130038398A (ko) | 2013-04-17 |
DE102007041039A1 (de) | 2009-03-05 |
US20110117329A1 (en) | 2011-05-19 |
KR20100115730A (ko) | 2010-10-28 |
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