CN107501527A - 一类基于1,8‑萘酰亚胺的高迁移率半导体聚合物及合成方法 - Google Patents

一类基于1,8‑萘酰亚胺的高迁移率半导体聚合物及合成方法 Download PDF

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CN107501527A
CN107501527A CN201710644393.3A CN201710644393A CN107501527A CN 107501527 A CN107501527 A CN 107501527A CN 201710644393 A CN201710644393 A CN 201710644393A CN 107501527 A CN107501527 A CN 107501527A
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袁忠义
朱国民
廉小翠
胡昱
张有地
陈义旺
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Nanchang University
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Abstract

一类基于1,8‑萘酰亚胺的高迁移率半导体聚合物及合成方法，结构式：步骤：(1)3,6‑二溴‑1,8‑萘酰亚胺合成；(2)将含电子给体单元Ar的双锡试剂单体与3,6‑二溴‑1,8‑萘酰亚胺在金属催化剂下反应，摩尔比为1﹕1；按溶剂与原料摩尔比300～400﹕1的量、催化剂与原料摩尔比0.02～0.1﹕1的量，加入溶剂和催化剂，无水无氧，反应温度100℃到溶剂回流温度。本发明聚合物对太阳光有较好的吸收，具有较好的光伏性能，成膜性好，迁移率高。

Description

一类基于1,8-萘酰亚胺的高迁移率半导体聚合物及合成方法
技术领域
本发明涉及聚合物的合成及聚合物应用于光电子材料与器件领域，特别涉及一类基于1,8-萘酰亚胺的高迁移率半导体聚合物及合成方法。
背景技术
随着社会的进步和科技的发展，能源危机备受关注，开发一种新的可再生能源成为广大科学工作者的追求，太阳能是一种绿色可再生资源，有机太阳能电池作为一种运用太阳能的手段，其核心活性层材料具有种类繁多、易于修饰、制备提纯简单和可制备大面积柔性器件的优势，具有商业化大面积生产应用的潜力。但是目前有机太阳能电池的光电转换的效率还不高，共轭分子材料种类开发不足，从活性层的角度来说，需要对光具有高的吸收效率以及高的载流子迁移率，因此，需要制备更多的新型聚合物材料。
由于有机半导体在有机发光显示器(OLED)，可印刷电子电路和有机太阳能电池中的各种应用，在过去几十年中一直是研究的热点。聚合半导体(共轭聚合物)与小分子半导体相比引起了特别的关注，因为它们具有良好的成膜性能，低成本的溶液加工工艺和高的载流子迁移率。受体材料(n型半导体，电子传输材料)与其供体材料(p型半导体，空穴传输材料)对应物相比更少，并且它们在电子电路中是必需的。作为明星受体分子PCBM，它们具有成本高，难变形，可见光吸收弱的缺点，因此，迫切需要开发高效的受体材料。具有刚性共轭体系的1,4,5,8-萘二酰亚胺(NDI)，高稳定性和强电子接受能力是一类优良的受体材料(中国专利CN106045998A)。以NDI作为母体的聚合受体已经在有机薄膜晶体管(OTFT)和有机太阳能电池中展现出各种应用(中国专利CN106459748A)。酰亚胺类被广泛用于构建高性能受体，例如，基于邻苯二甲酰亚胺有机半导体的小分子和聚合物已广泛用于OTFT和有机太阳能电池。1,8-萘酰亚胺(NMI)具有与NDI类似的结构和能级，其小分子半导体在荧光探针(中国专利CN106867521A)，OTFT和有机太阳能电池中已经被广泛应用。然而，由于合成和纯化困难的原因，基于NMI的共轭聚合物从未报道。
发明内容
本发明的目的在于提供一类基于1,8-萘酰亚胺的高迁移率半导体聚合物及合成方法。
本发明通过以下技术方案实现的。
本发明所述的一类基于1,8-萘酰亚胺的高迁移率半导体聚合物，其结构式如下：
其中R1为1-30个碳原子的直链、支链或者环状烷基链的烷烃，Ar为电子给体单元，n为1-1000的自然数，其中所述Ar为如下结构的一种或两种以上：
其中R2，R3为氢原子或烷基链，或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、硝基、苯基或噻吩取代基，或其中一个或多个氢原子被卤素原子取代。
本发明所述的一类基于1,8-萘酰亚胺的高迁移率半导体聚合物的合成方法，按如下步骤：
(1)3,6-二溴-1,8-萘酰亚胺母体合成(依据中国专利CN106749017A)。
(2)金属催化偶联反应：将含电子给体单元Ar的双锡试剂单体与3,6-二溴-1,8-萘酰亚胺在金属催化剂下反应，摩尔比为1﹕1。按溶剂与原料摩尔比300～400﹕1的量、催化剂与原料摩尔比0.02～0.1﹕1的量，加入溶剂和催化剂，无水无氧，反应温度100℃到溶剂的回流温度条件下，进行金属催化偶联反应，得到基于1,8-萘酰亚胺的高迁移率半导体聚合物。
本发明所述的溶剂为N,N-二甲基甲酰胺和甲苯的混合溶剂，其体积混合比例为1:1-20。
本发明所述的金属催化剂为Pd2(dba)3/P(o-tol)3、Pd(PPh3)2Cl2或Pd(PPh3)4等。
本发明所制备的共轭聚合物对太阳光有较好的吸收，具有较好的光伏性能，此类聚合物具有成膜性好，迁移率高的特点。
附图说明
图1为聚合物D4的空间电荷限制电流法测试的电子迁移率的J-V曲线。
图2为聚合物D5的空间电荷限制电流法测试的电子迁移率的J-V曲线。
具体实施方式
本发明将通过以下实施例作进一步说明。
实施例1。聚合物D1合成。
氩气保护下，在50mL反应瓶内，加入反应物DBNMI(191.4mg，0.3mmol)，反应物A(271.0mg，0.3mmol)，四(三苯基膦)钯(10mg)、甲苯(10mL)和N，N-二甲基甲酰胺(1mL)，回流反应24h，待反应降至室温后将反应液沉析在甲醇中，先后用甲醇、丙酮、正己烷进行索氏抽提，干燥，得到暗红色固体(379.2mg)，产率:82％。数均分子量：59150，分散指数：1.31(1,2,4-三氯苯为流动相，聚苯乙烯为标准)。
1HNMR(300MHz,CDCl3)δH:8.35-6.34(m)，δH:1.46-0.86(m)。
实施例2。聚合物D2合成。
氩气保护下，在50mL反应瓶内，加入反应物DBNMI(201.1mg，0.32mmol)，反应物B(158.1mg，0.34mmol)，四(三苯基膦)钯(10mg)、甲苯(10mL)和N，N-二甲基甲酰胺(1mL)，待反应降至室温后将反应液沉析在甲醇中，先后用甲醇、丙酮、正己烷进行索氏抽提，干燥，得到暗红色固体(312.5mg)，产率:87％。数均分子量：17150，分散指数：1.43(1,2,4-三氯苯为流动相，聚苯乙烯为标准)。
1HNMR(300MHz,CDCl3)δH:8.42-6.12(m)，δH:1.44-0.84(m)。
实施例3。聚合物D3合成。
氩气保护下，在50mL反应瓶内，加入反应物DBNMI(200.5mg，0.32mmol)，反应物C(134.4mg，0.33mmol)，四(三苯基膦)钯(10mg)、甲苯(10mL)和N，N-二甲基甲酰胺(1mL)，待反应降至室温后将反应液沉析在甲醇中，先后用甲醇、丙酮、正己烷进行索氏抽提，干燥，得到黄色固体(281.3mg)，产率:84％。数均分子量：19130，分散指数：1.38(1,2,4-三氯苯为流动相，聚苯乙烯为标准)。
1HNMR(300MHz,CDCl3)δH:8.45-6.07(m)，δH:1.45-0.85(m)。
实施例4。聚合物D4合成。
氩气保护下，在50mL反应瓶内，加入反应物DBNMI(299.3mg，0.471mmol)，反应物D(232.2mg，0.472mmol)，四(三苯基膦)钯(10mg)、甲苯(10mL)和N，N-二甲基甲酰胺(1mL)，回流反应24h，待反应降至室温后将反应液沉析在甲醇中，先后用甲醇、丙酮、正己烷进行索氏抽提，干燥，得到暗红色固体(446.5mg)，产率:84％.数均分子量：28450，分散指数：1.24(1,2,4-三氯苯为流动相，聚苯乙烯为标准)。
1HNMR(300MHz,CDCl3)δH:8.44-6.08(m)，δH:1.46-0.86(m)。
实施例5。聚合物D5合成。
氩气保护下，在50mL反应瓶内，加入反应物DBNMI(298.7mg，0.470mmol)，反应物E(270.9mg，0.472mmol)，四(三苯基膦)钯(10mg)、甲苯(10mL)和N，N-二甲基甲酰胺(1mL)，待反应降至室温后将反应液沉析在甲醇中，先后用甲醇、丙酮、正己烷进行索氏抽提，干燥，得到暗红色固体(484.2mg)，产率:85％。数均分子量：32150，分散指数：1.26(1,2,4-三氯苯为流动相，聚苯乙烯为标准)。
1HNMR(300MHz,CDCl3)δH:8.53-6.02(m)，δH:1.46-0.86(m)。

Claims (4)

1.一类基于1,8-萘酰亚胺的高迁移率半导体聚合物，其特征是结构式如下：
其中R1为1-30个碳原子的直链、支链或者环状烷基链的烷烃，Ar为电子给体单元，n为1-1000的自然数，其中所述Ar为如下结构的一种或两种以上：
其中R2，R3为氢原子或烷基链，或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、硝基、苯基或噻吩取代基，或其中一个或多个氢原子被卤素原子取代。
2.权利要求1所述的一类基于1,8-萘酰亚胺的高迁移率半导体聚合物的合成方法，其特征是按如下步骤：
(1)3,6-二溴-1,8-萘酰亚胺的合成；
(2)将含电子给体单元Ar的双锡试剂单体与3,6-二溴-1,8-萘酰亚胺在金属催化剂下反应，摩尔比为1﹕1；按溶剂与原料摩尔比300～400﹕1的量、催化剂与原料摩尔比0.02～0.1﹕1的量，加入溶剂和催化剂，无水无氧，反应温度100℃到溶剂的回流温度条件下，进行金属催化偶联反应，得到基于1,8-萘酰亚胺的高迁移率半导体聚合物。
3.根据权利要求2所述的一类基于1,8-萘酰亚胺的高迁移率半导体聚合物的合成方法，其特征是所述的溶剂为N,N-二甲基甲酰胺和甲苯的混合溶剂，其体积混合比例为1:1-20。
4.根据权利要求2所述的一类基于1,8-萘酰亚胺的高迁移率半导体聚合物的合成方法，其特征是所述的金属催化剂为Pd2(dba)3/P(o-tol)3、Pd(PPh3)2Cl2或Pd(PPh3)4。
CN201710644393.3A 2017-08-01 2017-08-01 一类基于1,8‑萘酰亚胺的高迁移率半导体聚合物及合成方法 Pending CN107501527A (zh)

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