CN114524918A - 一种导电聚合物及其合成方法与应用 - Google Patents
一种导电聚合物及其合成方法与应用 Download PDFInfo
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Abstract
本发明属于有机半导体材料技术领域,具体涉及一种导电聚合物及其合成方法与应用,本发明公开的导电聚合物的主链结构为以苯并二唑或苯并三唑为基本重复单元,与Ar重复单元聚合而成,由于苯并二唑或苯并三唑等重复单元化学稳定性及化学修饰性强,有利于取代基或者侧链的引入。此外,通过在与苯并二唑或苯并三唑等重复单元相连的噻吩上引入烷基链或乙二醇侧链,能够提升聚合物分子的溶解性,所得聚合物可溶于一般溶剂,如二氯甲烷、氯仿、甲苯等。本发明的导电聚合物具有结构确定,合成简单等特点,可作为通道活性材料应用于有机电化学晶体管的有机半导体层中,具有良好的性能。
Description
技术领域
本发明属于有机半导体材料技术领域,具体涉及一种导电聚合物及其合成方法与应用。
背景技术
生物有机电子学能够解决生物医学在诊疗上的许多问题,例如它可以对低浓度的生物分析物、微弱的生物电信号以及一些病原体展开检测,用途极广。其中,最具代表性的生物有机电化学材料当属有机电化学晶体管(OECTS)。OECTS灵敏度高,只需要很小的电压就能开展工作,制备工艺也十分简单,除此之外,它与生物有良好的兼容性、能快速响应。这些特点使得OECTS被广泛用于检测神经元的生物信号、检测多种分析物等方面,同时良好的生物相容性使其可被用来制造可穿戴设备。
OECT主要由源极、漏极、栅极、有机半导体层和衬底五个部分构成,其中最主要的部分是有机半导体,通常以导电聚合物作为OECTS通道的活性材料。早期的OECT通道材料有聚吡咯(PPy)和聚苯胺(PANI)。而PPy由于易被氧化不稳定性,且掺杂PPy的聚合物具有交联的倾向,会导致设备无法操作,因而限制了PPy作为活性层材料的应用。PANI则由于在电解质中具有优异的稳定性、易于合成且初始材料成本较低,被认为是OECT的合适材料,但它需要在低pH下运行,这也限制了其在生物相关传感中的进一步应用。之后,PPy和PANI逐渐被PEDOT:PSS(聚乙撑二氧噻吩-聚苯乙烯磺酸盐)所替代。PEDOT:PSS可以说是OECT中应用最成功的材料,与PPy和PANI相比,它有着更高的电荷传输、存储能力。然而,虽然PEDOT:PSS作为通道材料在器件的gm、开关速度和稳定性方面显著提高OECT的性能,但PEDOT:PSS仍然存在一些缺点,如结构复杂、PSS呈酸性、体积电容有限等等。为了解决PEDOT:PSS的这些不足,在过去的几年里开发出了接有乙二醇侧链的半导体聚合物,该聚合物以乙二醇为极性链,能很好的与水接触,通过极性链离子能够进入导电聚合物内,实现掺杂,从而极大的丰富了OECT通道材料的选择。但当前的OECT导电聚合物种类较为单一,有必要进一步加大开发力度,以丰富OECT通道材料。
发明内容
为了克服上述现有技术的不足,本发明的首要目的是提供一种导电聚合物。
本发明的第二个目的是提供上述导电聚合物的合成方法。
本发明的第三个目的是提供上述导电聚合物的应用。所述导电聚合物可作为通道活性材料应用于有机电化学晶体管的有机半导体层中,具有良好的性能。
本发明的上述第一个目的是通过以下技术方案来实现的:
一种导电聚合物,所述导电聚合物的结构式如下所示:
式中,n为自然数;X为O、S、Se、NR中的一种,R为烷烃;Y为H、F、R、PEG中的一种;a为1或2;Ar选自Ar1、Ar2、Ar3、Ar4中的任意一种,Ar1、Ar2、Ar3、Ar4中的m=1-6:
上述的导电聚合物由苯并二唑或苯并三唑等重复单元与Ar聚合而得,该类聚合物材料具有结构确定,合成简单等特点。
作为本发明的一个优选实施方式,当上述的导电聚合物中的X为S,Y为F,a取1,Ar2中m取3时,所述导电聚合物具有以下的结构式:
本发明的上述第二个目的是通过以下技术方案来实现的:
本发明还提供了上述导电聚合物(P1)的制备方法,具体为:在惰性气体保护环境下,以三(二亚苄基丙酮)二钯和三(邻甲基苯基)膦为催化剂,由化合物A和化合物B在有机溶剂中经Stille偶合反应后制备得到,化合物A和化合物B的结构式如下所示:
优选地,所述化合物A与化合物B的摩尔比为1:1。
优选地,所述三(二亚苄基丙酮)二钯与三(邻甲基苯基)膦的摩尔比为1:4。
优选地,所述三(二亚苄基丙酮)二钯与化合物A的摩尔比为(0.01~0.03):1。具体地,所述三(二亚苄基丙酮)二钯与化合物A的摩尔比为0.03:1。
优选地,反应的温度为110~130℃,时间为24~48h。具体地,反应的温度为120℃,时间为24h。
优选地,所述有机溶剂包括无水甲苯。
本发明的上述第三个目的是通过以下技术方案来实现的:
本发明还提供了上述导电聚合物在制备有机电化学晶体管中的应用。
经测试发现,上述导电聚合物(P1)可作为通道活性材料应用于有机电化学晶体管的有机半导体层中,具有良好的性能。
与现有技术相比,本发明的有益效果是:
本发明公开了一种导电聚合物,该聚合物的主链结构为以苯并二唑或苯并三唑为基本重复单元,与Ar重复单元聚合而成,由于苯并二唑或苯并三唑等重复单元化学稳定性及化学修饰性强,有利于取代基或者侧链的引入。此外,通过在与苯并二唑或苯并三唑等重复单元相连的噻吩上引入烷基链或乙二醇侧链,能够提升聚合物分子的溶解性,所得聚合物可溶于一般溶剂,如二氯甲烷、氯仿、甲苯等。总体而言,本发明的导电聚合物具有结构确定,合成简单等特点,可作为通道活性材料应用于有机电化学晶体管的有机半导体层中,具有良好的性能。
附图说明
图1为化合物A的1H NMR谱图;
图2为化合物B的1H NMR谱图;
图3为基于导电聚合物P1的OECT器件的输出曲线(VDS为栅源电压,IDS为栅源电压);
图4为基于导电聚合物P1的OECT器件的转移曲线(VGS为开启电压,IDS为栅源电压,gm为跨导);
图5为导电聚合物P1在溶液(Sol)中以及制成薄膜(Film)后的紫外吸收光谱。
具体实施方式
下面对本发明的具体实施方式作进一步说明。在此需要说明的是,对于这些实施方式的说明用于帮助理解本发明,但并不构成对本发明的限定。此外,下面所描述的本发明各个实施方式中所涉及的技术特征只要彼此之间未构成冲突就可以相互组合。
下述实施例中的实验方法,如无特殊说明,均为常规方法,下述实施例中所用的试验材料,如无特殊说明,均为可通过常规的商业途径购买得到。
以下具体实施方式采用瑞士Bruker公司生产的AVANCE III 400M型液体核磁共振谱仪来检测产物的1HNMR谱图,溶剂为氘代氯仿(CDCl3)。采用瑞士Bruker生产的solariX质量分析飞行质谱仪(MaldiTOF)来表征分子量。
实施例1一种基于苯并噻二唑的导电聚合物(P1)的制备方法
该基于苯并噻二唑的导电聚合物(P1)结构式如下:
P1的制备方法具体包括以下步骤:
(1)单体A的合成:单体A的合成根据下列反应方程式进行。
1)以100mL甲苯(Toluene)作为溶剂,以3-甲氧基噻吩(4.5674g,40mmol)与三乙二醇单甲醚(19.704g,120mmol)作为原料加入反应瓶中,再添加对甲苯磺酰胺(PTSA,0.689g,4mmol)作为催化剂,在100℃下反应20h。反应完成后通过减压蒸馏除去溶剂得到粗产物,粗产物痛过硅胶柱纯化得到目标产物A1,总计4.927g(产率50%);
2)在氮气状态下,往干燥的250mL圆底烧瓶中加入磁子和3.203g的A1(13mmol)以及100mL的干燥THF(四氢呋喃)。用低温反应器将圆底烧瓶冷却到-78℃后,再加入10.56mL1.6M的正丁基锂(16.9mmol),在-78℃反应1.5h,反应结束后用低温反应器中的乙醇将反应保持在-78℃下15min,并在次期间一次性加入1M的三甲基氯化锡19.5mL(19.5mmol),然后将温度逐渐回至室温,并继续搅拌12h。反应完后用饱和KF水溶液淬灭反应,所得反应液经分离后用水进行洗涤,并用二氯萃取水中的有机物,有机层用无水NaSO4干燥,减压蒸馏除去溶剂后得到粗产物A2(4.91g),无需纯化直接用于下一步;
3)将A2(4.91g),4,7-二溴-5,6-二氟-苯并噻二唑(1.466g,4.4mmol),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.122g,0.13mmol)以及三(邻甲基苯)磷配体(P(o-tol)3,0.162g,0.53mmol)加入圆底烧瓶中,抽充三次后再加入60mL干燥甲苯,在105℃下反应12h。反应完成后通过减压蒸馏除去溶剂得到粗产物,粗产物通过硅胶柱纯化得到化合物A3,总计1.454g(产率50%);
4)将化合物A3(1.388g,2.1mmol)加入到反应器中,然后加入20mL氯仿和乙酸的混合溶液(体积比为3:1),在冰水浴下,再缓慢加入NBS(N-溴代丁二酰亚胺,0.374g,2.1mmol),反应12h,所得反应液经分离后用水进行洗涤,并用二氯萃取水中的有机物,有机层用无水NaSO4干燥后用硅胶柱进行分离提纯得到1.547g单体A(产率90%)。图1为单体A的1HHMR图,证明了A的结构。
(3)单体B的合成:单体B的合成根据下列反应方程式进行。
1)以100mL甲苯(Toluene)作为溶剂,以3-甲氧基噻吩(4.5674g,40mmol)与二乙二醇单甲醚(14.418g,120mmol)作为原料加入反应瓶中,再添加对甲苯磺酰胺(PTSA,0.689g,4mmol)作为催化剂,在100℃下反应20h。反应完成后通过减压蒸馏除去溶剂得到粗产物,粗产物通过硅胶柱纯化得到化合物B1,总计4.045g(产率50%);
2)以B1(3.843g,19mmol)作为原料加入由冰块保温的反应瓶中,以THF(四氢呋喃)和正己烷作为溶剂(体积比9:1,其中四氢呋喃360mL,正己烷40mL)。加入溶剂后在冰水浴保温下再缓慢加入NBS(N-溴代琥珀酰亚胺,3.382g,19mmol),然后使反应瓶的温度回至室温搅拌12h。所得反应液经分离后用水进行洗涤,并用二氯萃取水中的有机物,有机层经无水NaSO4干燥并减压蒸馏后,用硅胶柱进行分离提纯,得到4.808g化合物B2(产率90%);
3)将化合物B2(4.78g,17mmol),双(1,5-环辛二烯)镍(Ni(COD)2,7.014g,25.5mmol),1,5-环辛二烯(COD,1.839g,17mmol)以及联吡啶(Bpy,3.514g,25.5mmol)加入圆底烧瓶中,抽充三次后再加入50mL无水THF(四氢呋喃),然后在66℃下回流6h。减压蒸馏除去溶剂后通过硅胶柱纯化得到3.421g液体B3(产率50%);
4)在氮气状态下,往干燥的250mL圆底烧瓶中加入磁子和3.220g的B3(8mmol)以及100mL的干燥THF(四氢呋喃)。用低温反应器将圆底烧瓶冷却到-78℃,再加入11.5mL 1.6M的正丁基锂(18.4mmol),并在-78℃反应1.5h,反应后用低温反应器中的乙醇将反应保持在-78℃下15min,此期间再一次性加入1M的三甲基氯化锡20mL(20mmol),然后逐渐将温度回至室温继续搅拌12h。反应完后用饱和KF水溶液淬灭反应,所得反应液经分离后用水进行洗涤,并用二氯萃取水中的有机物,有机层用无水NaSO4干燥,减压蒸馏除去溶剂得到粗产物,粗产物经凝胶渗透色谱法(GPC)纯化后得到2.913g的固体产物单体B(产率50%)。图2为单体B的1H HMR图,证明了其结构。
(3)P1的制备:单体A和B通过stille交叉偶联反应聚合形成P1,该反应是一种有机亲电试剂与有机锡试剂(锡则在后续的萃取步骤中被洗掉)之间的交叉偶联反应,具体制备过程如下:
在真空手套箱内分别称取所制备的单体A(32.117mg,0.05mmol)和单体B(32.001mg,0.05mmol)于微波反应管内,并在反应管内取0.5mL无水甲苯作为溶剂,取三(邻甲基苯基)膦(1.826mg,0.006mmol)作为配体、取三(二亚苄基丙酮)二钯(1.374mg,0.0015mmol)作为催化剂。将反应器密封后转移至常压环境中,设置反应温度为120℃,反应24小时。反应结束冷却至室温后,聚合物在甲醇中沉降出来,然后通过滤纸筒对聚合物进行过滤,再用索氏提取器进行萃取,萃取所用溶剂依次为甲醇、丙酮、正己烷、二氯甲烷、氯仿。最后对氯仿溶液进行浓缩后聚合物在甲醇中沉降出来,之后经过滤和干燥即可得到聚合物P1。所得聚合物P1可溶于一般溶剂,如二氯甲烷、氯仿、甲苯等。
将所得导电聚合物P1制作成OECT器件,OECT的制作过程包括金电极的图案化和有机半导体材料在沟道中的沉积。首先在丙酮、水、异丙醇和浓硫酸与过氧化氢的混合溶液中依次清洗玻璃基底,然后用氮气干燥。使用光刻和真空蒸发镀膜技术在基底上沉积金电极,器件的沟道宽度(W)为100μm,长度(L)为10μm。配制5mg/mL的半导体(聚合物P1)溶液,通过旋涂法在沟道中沉积半导体层,分别以0.1M NaCl水溶液和Ag/AgCl电极作为电解液和栅极,最后使用半导体参数分析仪在环境条件下对器件进行测试表征。
图3、图4为该导电聚合物P1的输出和转移曲线,从图中可以得出聚合物制备的有机电化学晶体管其跨导为120uS。图5为该导电聚合物的紫外可见吸收光谱(UV-vis),由该聚合物在无水氯仿溶液中的吸收光谱可知,其响应范围在300-700nm之间,最大吸收峰在590nm处。将该聚合物溶于无水氯仿溶液并采用旋涂法制备成薄膜,由该薄膜的吸收光谱可知,其响应范围在300-800nm之间,最大吸收峰在670nm处。可见,导电聚合物P1可作为通道活性材料应用于有机电化学晶体管的有机半导体层中,具有良好的性能。
以上对本发明的实施方式作了详细说明,但本发明不限于所描述的实施方式。对于本领域的技术人员而言,在不脱离本发明原理和精神的情况下,对这些实施方式进行多种变化、修改、替换和变型,仍落入本发明的保护范围内。
Claims (9)
4.根据权利要求3所述的导电聚合物的制备方法,其特征在于,所述化合物A与化合物B的摩尔比为1:1。
5.根据权利要求3所述的导电聚合物的制备方法,其特征在于,所述三(二亚苄基丙酮)二钯与三(邻甲基苯基)膦的摩尔比为1:4。
6.根据权利要求3所述的导电聚合物的制备方法,其特征在于,所述三(二亚苄基丙酮)二钯与化合物A的摩尔比为(0.01~0.03):1。
7.根据权利要求3所述的导电聚合物的制备方法,其特征在于,反应的温度为110~130℃,时间为24~48h。
8.根据权利要求3所述的导电聚合物的制备方法,其特征在于,所述有机溶剂包括无水甲苯。
9.权利要求1或2所述的导电聚合物在制备有机电化学晶体管中的应用。
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