CN108192084A - 一种有机半导体共轭聚合物及其合成方法 - Google Patents

一种有机半导体共轭聚合物及其合成方法 Download PDF

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CN108192084A
CN108192084A CN201810042734.4A CN201810042734A CN108192084A CN 108192084 A CN108192084 A CN 108192084A CN 201810042734 A CN201810042734 A CN 201810042734A CN 108192084 A CN108192084 A CN 108192084A
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organic semiconductor
thienyl
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邱龙臻
黄凯强
丁亚飞
杜玉昌
张强
赵耀
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Hefei University of Technology
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Abstract

本发明公开了一种有机半导体共轭聚合物及其合成方法，具体是一类基于（噻吩基）吡咯并吡咯‑二酮‑异靛蓝‑（噻吩基）吡咯并吡咯‑二酮和双（2‑三甲基锡基）并噻吩的有机半导体共轭聚合物及其制备方法。本发明涉及合成的新型有机半导体共轭聚合物具有宽的吸收峰，覆盖可见光并且延伸至近红外区域，同时具有低的LUMO能级，可作为光伏材料应用于有机光伏领域，及作为给体‑受体（D‑A）共轭聚合物材料应用于有机薄膜场效应晶体管领域。同时，引入烷基侧链作为助溶基团。本发明所制得的有机共轭半导体聚合物溶液加工性好，在有机光伏及有机薄膜场效应晶体管领域有一定的应用前景。

Description

一种有机半导体共轭聚合物及其合成方法
技术领域
本发明涉及有机共轭聚合物领域，具体是一种有机半导体共轭聚合物及其合成方法。
背景技术
有机半导体共轭聚合物由于具有成本低廉、柔韧好性和可大规模溶液加工等优点，因此在有机薄膜场效应晶体管领域中有着广泛的应用前景。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，这是由于在D-A共轭聚合物中给体和受体分别具有给电子和吸电子的推拉相互作用，增强了分子内和分子间的作用力，极大的提高了体系内电荷的有效传输。目前高效吸电子受体的缺乏制约着相关D-A共轭聚合物器件的性能表现。主要原因在于D-A共轭聚合物最低未占轨道(LUMO)能级水平不够低(低于-4.0eV)，不利于电子的注入和电荷的稳定传输。根据之前的文献报道，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，从而能在共轭聚合物中实现高效的电子传输。因此，如果在D-A共轭聚合物中将一个吸电子单元A换成三个吸电子单元A1、A2和A3，并且将三个吸电子单元通过π单元(这里指噻吩环)连接形成A1-π-A2-π-A1的大共轭受体，之后再与给电子基团聚合(这里主要指噻吩类)能有效降低聚合物的LOMO能级，极大的增加电子的有效传输。
二吡咯并[3，4-c]吡咯-1，4-二酮(DPP)单元含有两个内酰胺基团使得整个DPP单元高度的缺电子，因此使其具有高的电子亲和势。噻吩取代的DPP单晶结构证实：DPP核上羰基氧原子与邻位噻吩上的氢原子之间存在一种类似于氢键的弱相互作用,使得噻吩取代DPP具有良好的共平面性,为分子骨架堆积提供了强的驱动力。异靛蓝(IID)为古老的染料靛蓝的同分异构体，以其强的吸电子能力，合成简单以及良好的化学可调性等特点，被广泛地应用于有机半导体聚合物材料中。
发明内容
本发明的目的是提供一种有机半导体共轭聚合物及其合成方法，在有机薄膜晶体管及其他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：
一种有机半导体共轭聚合物，其特征在于：该有机半导体共轭聚合物是基于(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮和双(2-三甲基锡基)并噻吩的半导体共轭聚合物，其结构式为：
其中，R1为C8-C24烷烃链，R2为C8-C20烷烃链，A2为异靛蓝类吸电子基团，D为噻吩类给电子基团，n≥1。
一种有机半导体共轭聚合物的合成方法，其特征在于：以(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴、双(2-三甲基锡基)并噻吩单体为原料，以三(二亚苄基丙酮)二钯为催化剂，以三苯基膦为配体，以氯苯为溶剂的体系下，采用Stille偶联反应得到所述的有机半导体共轭聚合物。
所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的偶联反应温度为120-130℃。
所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的偶联反应时间为10-12小时。
所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴单体、双(2-三甲基锡基)并噻吩单体、三(二亚苄基丙酮)二钯、三苯基膦的用量摩尔比为1：1：0.06：0.24。
本发明的优点是：
本发明涉及合成的新型有机半导体共轭聚合物具有宽的吸收峰，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DPP和IID的π-A1-π-A2-π-A1-π-D型共轭聚合物，在有机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，从而实现有机共轭聚合物的电子传输，使得聚合物具有低的最低未占轨道能级，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与有机光伏领域。
附图说明
图1为基于(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮和双(2-三甲基锡基)并噻吩的有机半导体共轭聚合物的合成路径示意图。
图2为(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴单体和双(2-三甲基锡基)并噻吩单体各自的合成路径示意图。
图3为实施例1中聚合物P1的合成路径示意图。
图4为可溶液加工的有机半导体共轭聚合物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(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴和双(2-三甲基锡基)并噻吩单体在Stille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C8-C24烷烃链，R2为C8-C20烷烃链，A2为异靛蓝类吸电子基团，D为并噻吩或者联噻吩类给电子基团，n≥1。
上述烷烃可选择直链或者支链，其中，R1优选C8-C14直链或C8-C24支链烷烃，R2优选C8-C12直链或C8-C20支链烷烃。
对各单体的制备方法进行说明，如下：
制备(噻吩基)吡咯并吡咯-二酮双溴单体
(噻吩基)吡咯并吡咯-二酮双溴单体的合成路径示意图如图2所示。双(2-三甲基锡基)并噻吩单体
双(2-三甲基锡基)并噻吩单体的合成路径如图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50mL反应管中加入0.036g双锡单体和0.2g双溴单体(R1和R2如表1所示)，再加入6mL氯苯，使用双排管做10min氮气置换后，将反应管放入液氮中。待体系完全固化后，配合双排管用油泵抽10min，再通入氮气平衡压力关闭油泵，然后将反应管放入乙醇中解冻。将以上步骤重复三次。最后向反应管中加入0.0045g的三(二亚苄基丙酮)二钯、和0.006g的三苯基膦，重复抽冻三次，于130℃反应12小时，将反应冷却至室温，加入200mL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2-3
具体步骤同实施例1：其具体结构如表1所示。
表1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有刚性的共平面结构，聚合物具有低的LUMO能级，可作为电子传输材料应用与有机薄膜晶体管中；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应用与有机光伏领域。

Claims (5)

1.一种有机半导体共轭聚合物，其特征在于：该有机半导体共轭聚合物是基于(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮和双(2-三甲基锡基)并噻吩的半导体共轭聚合物，其结构式为：
其中，R1为C8-C24烷烃链，R2为C8-C20烷烃链，A2为异靛蓝类吸电子基团，D为噻吩类给电子基团，n≥1。
2.一种有机半导体共轭聚合物的合成方法，其特征在于：以(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴、双(2-三甲基锡基)并噻吩单体为原料，以三(二亚苄基丙酮)二钯为催化剂，以三苯基膦为配体，以氯苯为溶剂的体系下，采用Stille偶联反应得到所述的有机半导体共轭聚合物。
3.根据权利要求2所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的偶联反应温度为120-130℃。
4.根据权利要求2所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的偶联反应时间为10-12小时。
5.根据权利要求2所述的一种有机半导体共轭聚合物的合成方法，其特征在于：所述的(噻吩基)吡咯并吡咯-二酮-异靛蓝-(噻吩基)吡咯并吡咯-二酮双溴单体、双(2-三甲基锡基)并噻吩单体、三(二亚苄基丙酮)二钯、三苯基膦的用量摩尔比为1：1：0.06：0.24。
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Cited By (3)

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CN109134477A (zh) * 2018-06-25 2019-01-04 中山大学 一种吡咯单酮的氮杂并四苯相似物及其制备方法和应用
CN114522727A (zh) * 2022-03-09 2022-05-24 太原理工大学 卤代芳香类线性共轭聚合物光催化材料及制备方法和应用
CN114773580A (zh) * 2022-04-29 2022-07-22 太原理工大学 非规整三元共轭聚合物光催化材料及其制备方法和应用

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