CN108948329A - 一种超低能级的共轭聚合物半导体材料及其制备方法 - Google Patents

一种超低能级的共轭聚合物半导体材料及其制备方法 Download PDF

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CN108948329A
CN108948329A CN201810599930.1A CN201810599930A CN108948329A CN 108948329 A CN108948329 A CN 108948329A CN 201810599930 A CN201810599930 A CN 201810599930A CN 108948329 A CN108948329 A CN 108948329A
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张国兵
汪霏霏
戴艳荣
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Hefei Xiliu Photoelectric Technology Co ltd
Wuhu Xiliu Photoelectric Technology Co ltd
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Abstract

本发明公开了一种超低能级的共轭聚合物半导体材料及其制备方法，该共轭聚合物结构式为：其中，R为C12‑C30烷烃链。该聚合物可以采用直接芳基化反应和Stille反应制备。本发明是结合联噻唑的弱缺电子特性和双(7‑氮杂‑3‑亚乙基)‑苯并二呋喃二酮)的强缺电子特性以及平面大π共轭结构来制备超低能级共轭聚合物半导体材料。本发明的材料可溶液加工，具有超低的LUMO和HOMO能级，可作为电子传输材料，应用于有机薄膜晶体管，有机光伏以及其它有机电子领域。

Description

一种超低能级的共轭聚合物半导体材料及其制备方法
技术领域
本发明涉及有机聚合物半导体材料领域，具体是一种超低能级的共轭聚合物半导体材料及其制备方法。
背景技术
近年来，共轭聚合物在有机薄膜晶体管，有机光伏和有机发光二极管(OLED)中的应用研究越来越引起人们的重视，与传统无机材料相比，聚合物为基础的半导体材料具有重量轻，成本低，柔性以及可以溶液加工等优点，使得共轭聚合物在柔性显示，传感器，能源等领域具有广阔的应用前景。到目前为止，聚合物半导体材料的性能发展非常迅速，其迁移率等性能已经达到甚至超过了商用的非晶硅。但是目前聚合物半导体材料绝大多数为空穴传输材料，电子传输型材料却相对落后，目前发展的电子传输材料基本上是在真空环境中，或者在惰性气体保护中实现的，在空气中实现的电子传输型聚合物半导体材料都是通过介电层来封装实现的。因此，聚合物半导体层不经过任何封装而能在空气中达到电子传输特性的聚合物非常少。聚合物半导体材料实现电子传输与聚合物半导体材料本身的最低未占轨道能级(LUMO)和最高占有轨道能级(HOMO)有关，低的LUMO能级有利于电子的有效注入和稳定传输，同时还能有效抵御空气中水和氧气的氧化，低的HOMO能级有利于阻止空穴的注入，从而实现在空气中稳定传输。因此设计和合成低LUMO/HOMO能级的聚合物半导体材料是实现空气中电子传输的有效途径。
发明内容
本发明是利用联噻唑和双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)这两种单元的优点，提供一种超低能级的共轭聚合物半导体材料及其制备方法。本发明的聚合物具有刚性的主链结构，通过支链引入烷基促进溶解，是可溶液加工的共轭聚合物半导体材料。本发明结构设计合理，聚合物具有超低的LUMO和HOMO能级，有望实现空气中长期稳定的电子传输特性。
本发明是通过以下技术方案来实现的：
第一方面，本发明涉及一种可溶液处理的超低能级的共轭聚合物半导体材料，所述共轭聚合物是基于联噻唑和双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)的半导体共轭聚合物；所述共轭聚合物的结构式为：
其中，R为C12-C30烷烃链。
更进一步地，所述的烷烃链可选择C12-C60的支链烷烃。
另一方面，本发明提供了上述超低能级的共轭聚合物半导体材料的制备方法，可采用两种方式制备，第一，可以用联噻唑和双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在直接芳基化反应条件下共聚；第二，可以采用双锡化的联噻唑单体与双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在Stille反应条件下共聚，用甲醇沉淀，然后用索氏提取提纯共轭聚合物。
所述共轭聚合物制备所用的单体结构分别如下所示：
直接芳基化反应所用单体为：
其中，R为C12-C30烷烃链；
Stille反应所用单体为：
其中，R为C12-C30烷烃链。
本发明具有如下有益效果：本发明披露的新型聚合物半导体材料是基于联噻唑的弱的缺电子特性，双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)的强缺电子特性以及共平面的大π共轭体系优势，以及引入侧链为柔性促溶的烷基链，制备一种新型的共轭聚合物半导体材料，具有超低的LUMO和HOMO能级，本发明所制得的共轭聚合物可以溶液加工，可应用于有机薄膜晶体管，有机光伏以及其它有机电子领域。
附图说明
图1为基于联噻唑和双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)的共轭聚合物半导体的合成路径示意图；
图2为实施例1和实施例2中聚合物的合成路径示意图；
图3为可溶性共轭聚合物P1的紫外光谱；
图4为可溶性共轭聚合物的电化学曲线图。
具体实施方式
下面结合附图对本发明的实施例做详细说明：本实例在以本发明技术方案为前提下进行实施，给出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，本发明中的共轭聚合物可采用两种方式制备，第一，可以用联噻唑和双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在直接芳基化反应条件下共聚；第二，也可以采用双锡化的联噻唑单体与双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在Stille反应条件下共聚，用甲醇沉淀，然后用索氏提取提纯共轭聚合物。
本发明的可溶液处理的超低能级的共轭聚合物半导体材料具有如下结构：
其中，R为C12-C30烷烃链。
实施例1：直接芳基化反应制备共轭聚合物P1
聚合物P1采用直接芳基化反应的合成路线如图2所示，具体步骤为：在100mL反应瓶中加入联噻唑0.14mmol，双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)0.14mmol，加入无水甲苯(也可以为四氢呋喃和氯苯)20mL，除氧，再加入钯催化剂2％，配体8％，异戊醇0.14mmol，碳酸铯0.42mmol，于110℃反应48小时，将反应冷却至室温，加入100mL甲醇沉淀，过滤得到固体，依次用甲醇、正己烷和氯仿提取，收集氯仿组份，旋干后再用甲醇沉淀得到黑色聚合物。
实施例2：Stille反应制备共轭聚合物P1
聚合物P1采用Stille反应的合成路线如图2所示，具体步骤为：在100mL反应瓶中加入双锡化的联噻唑0.14mmol，双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)0.14mmol，加入无水甲苯(也可以为四氢呋喃和氯苯)20mL，除氧，再加入钯催化剂2％，配体8％，于110℃反应48小时，将反应冷却至室温，加入100mL甲醇沉淀，过滤得到固体，依次用甲醇、正己烷和氯仿提取，收集氯仿组份，旋干后再用甲醇沉淀得到黑色聚合物。
图3给出了聚合物P1的紫外吸收光谱，其最大吸收峰位于787nm，光学能带隙为1.78eV。
图4给出了聚合物P1的电化学测试结果，其LUMO能级为-4.28eV，HOMO能级为-6.06eV。

Claims (4)

1.一种超低能级的共轭聚合物半导体材料，其特征在于：所述共轭聚合物是基于联噻唑和双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)的半导体共轭聚合物；所述共轭聚合物的结构式为：
其中，R为C12-C30烷烃链。
2.根据权利要求1所述的一种超低能级的共轭聚合物半导体材料，其特征在于：所述的烷烃链可选择C12-C60的支链烷烃。
3.一种如权利要求1所述的超低能级的共轭聚合物半导体材料的制备方法，其特征在于：所述共轭聚合物可采用两种方式制备，第一，可以用联噻唑和双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在直接芳基化反应条件下共聚；第二，可以采用双锡化的联噻唑单体与双溴化的双(7-氮杂-3-亚乙基)-苯并二呋喃二酮)在Stille反应条件下共聚，用甲醇沉淀，然后用索氏提取提纯共轭聚合物。
4.根据权利要求3所述的超低能级的共轭聚合物半导体材料的制备方法，其特征在于：所述共轭聚合物制备所用的单体结构分别如下所示：
直接芳基化反应所用单体为：
其中，R为C12-C30烷烃链；
Stille反应所用单体为：
其中，R为C12-C30烷烃链。
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CN111518121A (zh) * 2020-05-14 2020-08-11 陕西理工大学 一种氨基苯并二呋喃二酮基低聚物及其制备方法和应用、有机场效应晶体管
CN113136024A (zh) * 2020-01-19 2021-07-20 中国科学院化学研究所 一种聚合物及其制备方法和应用以及有机场效应晶体管
CN113881019A (zh) * 2021-10-18 2022-01-04 福州大学 一种基于2-吲哚酮的聚合物给体材料及其制备方法

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