CN109553757A - 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用 - Google Patents

一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用 Download PDF

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CN109553757A
CN109553757A CN201811573149.3A CN201811573149A CN109553757A CN 109553757 A CN109553757 A CN 109553757A CN 201811573149 A CN201811573149 A CN 201811573149A CN 109553757 A CN109553757 A CN 109553757A
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邓平
朱笔李
蔡洋
姬敬敬
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Abstract

本发明公开了一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用。其先通过炔键偶联反应合成一种带炔键的单体M1，然后将其与带溴基的单体M2加热聚合，通过炔键与溴的作用制得所述二维结构的萘二酰亚胺类受体聚合物。该聚合物中含有多个炔键，使分子间的共平面性和相互作用力得到了提高。该二维结构的萘二酰亚胺类受体聚合物具有迁移率高、化学稳定性好等优点，将其溶解于氯仿、氯苯等卤代溶剂中，可以通过溶液旋涂成膜，用于有机太阳能电池的制备中。

Description

一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与 应用
技术领域
本发明涉及一种含有多羰基、π-π堆积作用及多炔键构成的二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用，属于有机太阳能电池受体材料领域。
背景技术
太阳能电池是一种直接有效的将清洁的太阳能转化成电能的有效方式。因为可作为清洁廉价的新能源代替目前广泛开采的石油、煤、天然气等而受到人们极大关注。和其他太阳能电池一样，有机太阳能电池的原理也是利用光生伏特现象，不同之处则在于，其利用聚合物吸收光子后产生的激子扩散到共轭聚合物/PCBM异质结界面处而发生电荷分离（参见文献: M C Scharber and N S Sariciftci. Efficiency of bulk-heterojunctionorganic solar cells[J]. Progress in Polymer Science,2013,38(12):1929.）。
有机太阳能电池的研究核心是PCE（光电转化效率），因此，提高光电转化效率是这一领域科学家共同追求的目标。有机太阳能电池一般由给体材料与受体材料组成，其性能取决于聚合物骨架的化学结构。一种良好的有机太阳能受体材料应该具有与太阳光地面辐射光谱匹配的光谱响应范围，以及载流子迁移率高、电极对其收集效率高等等特点（参见文献：M Kaltenbrunner, M S White, E D Głowacki, et al.Ultrathin and lightweightorganic solar cells with high flexibility[J].Nature communications,2011,3(1):85-100.）。
发明内容
本发明的目的在于提供一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用，其具有光电转化效率高、化学稳定性好、平面性优异等优点，在有机太阳能电池受体材料领域具有巨大的应用前景。
为实现上述目的，本发明采用如下技术方案：
本发明第一个目的是保护一种二维结构的萘二酰亚胺类受体聚合物，其结构式为：
，式中，R1为C6~C20的烷基链，R2为C20~C29，n≥1。
本发明第二个目的是保护所述二维结构的萘二酰亚胺类受体聚合物的制备方法，其是将单体M1、M2与催化剂Pd(PPh3)4、CuI溶于无水卤代有机溶剂中，在氮气下加热回流进行聚合后，经索氏提取进行提纯，高温真空干燥获得所述聚合物；
其中，单体M1的结构式为：
（R1为C6~C20的烷基链）；
单体M2的结构为：
（R2为C20~C29）；
所述卤代有机溶剂为氯苯、邻二氯苯等。
所述单体M1的制备方法如下：
（1）按摩尔比1:1.3将NDI化合物A（）与噻吩乙腈化合物B（）溶解于有机溶剂中，加入6%当量的PdCl2(PPh3)2与6%当量的CuI，80℃加热回流过夜后，经萃取、硅胶柱层析提纯、干燥，得到中间化合物C，其结构式为：
；
（2）按摩尔比1:0.75将步骤（1）所得的中间化合物C与2,5-二溴对苯二甲醛加入有机溶剂中，再加入5mol%的四丁基氢氧化铵，50℃反应6小时，通过过滤重结晶的方法得到红色粉末，即为单体M1的前置体D，其结构式为：
；
（3）将步骤（2）所得前置体D与过量三甲基硅基乙炔溶于有机溶剂，加入Pd(PPh3)4、CuI，加热回流后，经萃取、柱层析提纯、干燥得到带TMS保护的单体M1，再将其溶于二氯甲烷与甲醇的混合溶液中（1:1，v/v）中，加入5当量的碳酸钾进行去保护，脱掉TMS得到所述单体M1。
所述有机溶剂为三乙胺、甲醇、二氯甲烷、二异丙胺、叔丁醇等。
本发明第三个目的是保护所述二维结构的萘二酰亚胺类受体聚合物在制备有机太阳能电池上的应用。
本发明的显著优点:
（1）本发明所采用的原料相对廉价，合成路径不复杂；
（2）本发明所制得的聚合物具有高度平面性及化学稳定性好等优点；
（3）将本发明所得二维结构的萘二酰亚胺类受体聚合物易于旋涂成膜，具有较好吸光范围和良好的化学稳定性且其光伏器件性能较好。
附图说明
图1为实施例1中的异辛烷的NDI化合物A的核磁共振氢谱。
图2为实施例2所得间化合物C的核磁共振氢谱。
图3为实施例3所得单体M1前置体D的核磁共振氢谱。
图4为实施例4所得单体M1的核磁共振氢谱。
图5为实施例6所得聚合物在溶液状态及薄膜状态下的紫外光谱图。
图6为实施例6所得聚合物的CV曲线图。
图7为实施例6所得聚合物的器件性能。
具体实施方式
为了使本发明所述的内容更加便于理解，下面结合具体实施方式对本发明所述的技术方案做进一步的说明，但是本发明不仅限于此。
实施例1 含有异辛烷的NDI化合物A制备
按文献《Caitlin S. Sample, Eisuke Goto, Modular synthesis of asymmetricrylene derivatives, Journal of Materials Chemistry C., 2017, 5,1052-1056》制备含有异辛烷的NDI化合物A，其结构式为：
。
实施例2 中间化合物C的制备
将1.79 g（4.62 mmol）实施例1制得的含有异辛烷的NDI，与0.85g（5.76mmol）噻吩乙腈化合物B（）溶于20 mL三乙胺中，加入202.4mg（0.28mmol）PdCl2(PPh3)2与54.9mg（0.28mmol）CuI，在氮气氛围下80℃反应过夜，反应结束后旋干三乙胺，使用二氯甲烷萃取，经硅胶柱提纯（洗脱剂为石油醚:二氯甲烷=2:1，v/v），得到中间化合物C（），产率为52.31%。1H NMR (500 MHz, Chloroform-d) δ 8.67 (ddd, J =8.4, 4.7, 1.2 Hz, 2H), 8.58 (d, J = 7.6 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H),7.88 (dd, J = 8.3, 7.3 Hz, 1H), 7.37 (d, J = 3.7 Hz, 1H), 7.10 (dt,J = 3.6,1.1 Hz, 1H), 5.37 (s, 1H), 4.15 (qd, J = 12.9, 7.3 Hz, 2H), 3.99 (d, J = 1.0Hz, 2H), 2.28 – 2.21 (m, 1H), 2.11 – 2.01 (m, 1H), 2.01 – 1.94 (m, 1H), 1.70– 1.63 (m, 1H), 1.46 – 1.31 (m, 5H), 1.29 (d, J = 6.8 Hz, 3H), 0.93 (dt, J =27.6, 7.2 Hz, 7H)。
实施例3 前置体D的制备
将200mg（0.44 mmol）实施例2制得的中间化合物C，与60.54mg（0.33mmol）2,5-二溴对苯二甲醛溶于20 ml叔丁醇中，然后加入0.2mL、1mol/L的四丁基氢氧化铵，在氮气氛围下50℃搅拌反应6小时，反应结束后冷却至室温，甲醇过滤除去红色固体，使用氯仿与丙酮重结晶，得到单体M1的前置体D，产率为15.6%。1H NMR (400 MHz, Chloroform-d) δ 8.66 (s,4H), 8.58 (d, J = 8.0 Hz, 2H), 8.41 (s, 2H), 7.97 (d, J = 7.7 Hz, 2H), 7.88(s, 1H), 7.65 (s, 1H), 7.47 (d, J = 13.0 Hz, 4H), 4.13 (s, 4H), 1.95 (s, 2H),1.54 (s, 14H), 1.35 (d, J = 32.9 Hz, 20H), 0.91 (d, J = 22.7 Hz, 14H)。
实施例4 单体M1的制备
将400mg（0.34 mmol）实施例3制得的前置体D与过量三甲基硅基乙炔溶于有机溶剂，加入18.9 mg（0.016mmol）Pd(PPh3)4、3.13 mg（0.016 mmol）CuI，加热回流后，经萃取、快速粗糙二氯甲烷柱层析提纯、干燥，得到带TMS保护的单体M1，再将其溶于二氯甲烷与甲醇的混合溶液中（1:1，v/v）中，加入5当量的碳酸钾进行去保护，脱掉TMS经过二氯甲烷快速过柱得到所述单体M1（）。1HNMR (500 MHz, Chloroform-d) δ 8.72 – 8.64 (m, 4H), 8.63 – 8.54 (m, 4H), 8.02– 7.84 (m, 4H), 7.54 – 7.42 (m, 4H), 5.32 (s, 8H), 4.17 – 4.10 (m, 2H), 2.02(s, 2H), 1.28 (s, 2H), 1.25 (s, 26H), 1.24 (s, 4H), 0.93 – 0.84 (m, 6H)。
实施例5 单体M2的制备
按文献《Pahlavanlu, P.;Tilley, A. J.;McAllister, B. T.; Seferos, D. S.,Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Moleculesand Polymers. J Org Chem 2017, 82 (23), 12337-12345.》制备单体M2，其结构式为：
。
实施例6 二维结构的萘二酰亚胺类受体聚合物的制备
将75 mg（0.069mmol）实施例4制得的单体M1与79.5 mg（0.069 mmol）与实施例5所得单体M2，7.9 mg（0.069mmol）Pd(PPh3)4、0.92 mg（0.6 mmol）CuI一同溶于5 mL氯苯与二异丙胺的混合溶液（1:1，v/v）中，在氮气气氛下80℃反应72小时，倒入甲醇中过滤，经过索氏提取得到聚合物，产率90%。
实施例7 二维结构的萘二酰亚胺类受体聚合物应用于有机太阳能电池器件中
将5-15mg的受体聚合物和给体材料PTB7-Th溶于氯苯中制成薄膜，夹在电池嵌在玻璃的阴极和阳极之间，制得有机太阳能器件的电极结构。其中聚合物与给体材料的质量比为1:1时，测得光电转换效率达到2.6%。填充因子达到66%。
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。

Claims (4)

1.一种二维结构的萘二酰亚胺类受体聚合物，其特征在于，其结构式为：
，式中，R1为C6~C20的烷基链，R2为C20~C29，n≥1。
2.一种如权利要求1所述的二维结构的萘二酰亚胺类受体聚合物的制备方法，其特征在于，将单体M1、M2与催化剂Pd(PPh3)4、CuI溶于无水卤代有机溶剂中，在氮气下加热回流进行聚合后，经提纯、高温真空干燥获得所述聚合物；
其中，单体M1的结构式为：
；
单体M2的结构为：
。
3.根据权利要求2所述的二维结构的萘二酰亚胺类受体聚合物的制备方法，其特征在于，单体M1的制备方法如下：
（1）将NDI化合物A与噻吩乙腈化合物B溶解于有机溶剂中，加入PdCl2(PPh3)2、CuI，加热回流后，经萃取、提纯、干燥，得到中间化合物C，其结构式为：
；
其中，所述NDI化合物A的结构式为：
；
所述噻吩乙腈化合物B的结构式为：
；
（2）将步骤（1）所得的中间化合物C与2,5-二溴对苯二甲醛在有机溶剂中反应，得到前置体D，其结构式为：
；
（3）将步骤（2）所得前置体D与三甲基硅基乙炔溶于有机溶剂，加入Pd(PPh3)4、CuI，加热回流后，经萃取、柱层析提纯、干燥得到带TMS保护的单体M1，再将其溶于有机溶剂中，加入5当量的碳酸钾进行去保护，得到所述单体M1。
4.一种如权利要求1所述的二维结构的萘二酰亚胺类受体聚合物在制备有机太阳能电池上的应用。
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