CN108285527A - 一种a-d-a型半导体共轭聚合物及其合成方法 - Google Patents

一种a-d-a型半导体共轭聚合物及其合成方法 Download PDF

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CN108285527A
CN108285527A CN201810042754.1A CN201810042754A CN108285527A CN 108285527 A CN108285527 A CN 108285527A CN 201810042754 A CN201810042754 A CN 201810042754A CN 108285527 A CN108285527 A CN 108285527A
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邱龙臻
丁亚飞
黄凯强
杜玉昌
赵耀
张强
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Hefei University of Technology
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Abstract

本发明公开了一种A‑D‑A型半导体共轭聚合物及其合成方法，具体的是一种基于异靛蓝衍生物单元和（噻吩基）吡咯并吡咯‑二酮单元的半导体共轭聚合物及其制备。本发明涉及合成的新型半导体共轭聚合物由于带隙窄而具有宽的吸收峰，覆盖可见光甚至延伸至近红外区域，同时能有效调控聚合物的LUMO能级，增加材料的电子传输性能，可代替PCBM作为光伏受体材料应用于有机光伏领域。以引入的侧链为助溶烷基链，本发明所制得的共轭半导体聚合物可溶液加工处理，在有机薄膜晶体管和有机光伏领域有一定的应用前景。

Description

一种A-D-A型半导体共轭聚合物及其合成方法
技术领域
本发明涉及共轭聚合物领域，具体是一种A-D-A型半导体共轭聚合物及其合成方法。
背景技术
共轭聚合物由于具有质量轻、成本低和柔韧性等优点而有望在有机薄膜晶体管中获得广泛的应用。目前，共轭聚合物中研究最多的是给体-受体(D-A)共轭聚合物，这是由于D-A共轭聚合物的给体和受体存在的的推拉相互作用增强了分子內和分子间的作用力，大大提高了电荷的传输性能。根据以前的文献报道，在共轭聚合物中引入强吸电子取代基能有效的降低聚合物的LUMO能级，从而实现共轭聚合物的电子传输性能。因此，如果在D-A共轭聚合物中再引入一个吸电子单元A，将两个吸电子单元A与一个给电子单元D连接形成A-D-A型的共轭聚合物，能有效调控聚合物的LUMO能级，增加材料的电子传输性能，甚至能实现双极性电荷传输。
二吡咯并[3，4-c]吡咯-1，4-二酮(DPP)作为一种经典的高性能的红色颜料，已经在涂料、墨水、电子荧光器件和晶体管等方面有广泛的应用。DPP单元有好的共轭结构而具有强列的π-π相互作用，内酰胺基团使得整个DPP单元高度的缺电子，但是，对于噻吩取代的DPP而言，由于噻吩是强的给电子基团，整体显示的是一种给电子特性。异靛蓝(IID)是一个中心对称分子,它由2个对称的吲哚连接而成,同时在氮原子的邻位上引入强吸电子羰基,使得IID具有很强的吸电子作用，因此异靛蓝具有高的电子亲和势。这些优点使得(噻吩基)DPP和IID分别作为给体受体单元在合成共轭聚合物材料以及在有机薄膜晶体管的应用上引起了广泛的关注。
发明内容
本发明的目的是提供一种A-D-A型半导体共轭聚合物及其合成方法，该半导体共轭聚合物在有机薄膜晶体管及其它有机光电器件中有一定的应用。
为了达到上述目的，本发明所采用的技术方案为：
一种A-D-A型半导体共轭聚合物，其特征在于：该半导体共轭聚合物是基于异靛蓝衍生物和(噻吩基)吡咯并吡咯-二酮的半导体共轭聚合物，该半导体共轭聚合物的结构式为：
其中，R1为C10-C12烷烃链，R2为C2-C4烷烃链，n≥1。
所述的一种A-D-A型半导体共轭聚合物，其特征在于：在(噻吩基)吡咯并吡咯-二酮中引入两个异靛蓝衍生物作为电子受体单元，可以显著降低聚合物LUMO能级，提高电子传输性能，甚至可以实现双极性电荷传输。
一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：以异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体和联噻吩双锡单体为原料，以三(二亚苄基丙酮)二钯为催化剂，三(邻甲基苯基)磷为配体的体系下，采用Stile交叉偶联反应得到所述的A-D-A型半导体共轭聚合物。
所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的交叉偶联反应温度为90-130℃。
所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的交叉偶联反应时间为6-72小时。
所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体、联噻吩双锡单体、三(二亚苄基丙酮)二钯、三(邻甲基苯基)磷的用量摩尔比为1：1：0.02：0.08。
本发明的优点是：
本发明涉及合成的新型半导体共轭聚合物由于带隙窄而具有宽的吸收峰，覆盖可见光并延伸至近红外领域，发明的半导体聚合物是基于异靛蓝衍生物和(噻吩基)吡咯并吡咯二酮的A-D-A型共轭聚合物，在共轭聚合物中引入强吸电子取代基能有效的降低聚合物的LUMO能级，从而实现共轭聚合物的电子传输，甚至可以实现双极性电荷传输，可以作为电子传输材料应用于有机薄膜晶体管中，同时也可作为受体材料代替富勒烯应用于有机光伏领域。
附图说明
图1为基于异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝和联噻吩的半导体共轭聚合物的合成路径示意图。
图2为异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体和联噻吩双锡单体的合成路径示意图。
图3为实施例1中聚合物P1的合成路径示意图。
图4为可溶液加工的半导体共轭聚合物P1的紫外光谱图。
具体实施方式
下面结合附图对本发明的实施例作详细说明：本实施例在以本发明技术方案为前提下进行实施，结合了详细的实施方式和具体的操作过程，但本发明的保护范围不限于下述的实施例。
如图1所示，本发明以异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体和联噻吩双锡单体在Stile反应条件下共聚，用甲醇沉淀，然后索氏提取，得到目标聚合物。
本发明的可溶液加工的半导体共轭聚合物具有如下结构
其中，R1为C10-C12烷烃链，R2为C2-C4烷烃链，n≥1。
对各单体的制备方法进行说明，如下：
制备异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体
异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体的合成路径示意图如图2所示。
制备联噻吩双锡单体
联噻吩双锡单体的合成路径示意图如图2所示。
实施例1，合成聚合物P1
聚合物P1的合成路径如图3所示，具体步骤为：在100mL反应瓶中加入0.5mmol双锡单体和0.5mmol双溴单体，再加入10mL氯苯，用氮气置换40分钟，再加入2％催化剂三(二亚苄基丙酮)二钯，以8％三(邻甲基苯基)磷为配体，于130℃反应48小时，将反应冷却至室温，加入100mL甲醇沉淀，过滤固体，分别用甲醇和正己烷索氏提取24小时，再用二氯甲烷或者氯仿索氏提取24小时，最后旋蒸液体，甲醇沉淀得黑色聚合物。
实施例2-6
具体步骤同实施例1：在100mL反应瓶中加入0.5mmol双锡单体和0.5mmol双溴单体，加入氯苯10mL，氮气置换40分钟，再加入2％催化剂三(二亚苄基丙酮)二钯，以8％三(邻甲基苯基)磷为配体，于130℃反应48小时，冷却至室温，加入100mL甲醇沉淀，固体分别用甲醇和正己烷索氏提取24小时，再用氯仿索氏提取24小时，最后旋蒸液体，甲醇沉淀得黑色聚合物P2P3P4P5P6P7P8P9，其具体结构如表1所示。
表1为黑色聚合物结构表
图4给出了聚合物P1的吸收光谱，吸收峰覆盖可见光，并延伸至近红外区域。
综上所述，本发明涉及的新型半导体共轭聚合物具低的LUMO能级，同时LUMO能级可以调控，可作为电子传输材料或双极性电荷传输彩料应用于有机薄膜晶体管中；在可见光及近红外区域能有效吸收太阳光子能量，本发明的半导体共轭聚合物可代替PCBM应用于有机光伏领域。

Claims (6)

1.一种A-D-A型半导体共轭聚合物，其特征在于：该半导体共轭聚合物是基于异靛蓝衍生物和(噻吩基)吡咯并吡咯-二酮的半导体共轭聚合物，该半导体共轭聚合物的结构式为：
其中，R1为C10-C12烷烃链，R2为C2-C4烷烃链，n≥1。
2.根据权利要求1所述的一种A-D-A型半导体共轭聚合物，其特征在于：在(噻吩基)吡咯并吡咯-二酮中引入两个异靛蓝衍生物作为电子受体单元，可以显著降低聚合物LUMO能级，提高电子传输性能，甚至可以实现双极性电荷传输。
3.一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：以异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体和联噻吩双锡单体为原料，以三(二亚苄基丙酮)二钯为催化剂，三(邻甲基苯基)磷为配体的体系下，采用Stile交叉偶联反应得到所述的A-D-A型半导体共轭聚合物。
4.根据权利要求3所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的交叉偶联反应温度为90-130℃。
5.根据权利要求3所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的交叉偶联反应时间为6-72小时。
6.根据权利要求3所述的一种A-D-A型半导体共轭聚合物的合成方法，其特征在于：所述的异靛蓝-(噻吩基)吡咯并吡咯二酮-异靛蓝双溴单体、联噻吩双锡单体、三(二亚苄基丙酮)二钯、三(邻甲基苯基)磷的用量摩尔比为1：1：0.02：0.08。
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CN109280155A (zh) * 2018-09-18 2019-01-29 深圳大学 主链含有炔键或者烯键的聚合物及制备方法与晶体管
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Application publication date: 20180717