CN106905514B - 分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料、其制备方法与应用 - Google Patents

分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料、其制备方法与应用 Download PDF

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CN106905514B
CN106905514B CN201710208372.7A CN201710208372A CN106905514B CN 106905514 B CN106905514 B CN 106905514B CN 201710208372 A CN201710208372 A CN 201710208372A CN 106905514 B CN106905514 B CN 106905514B
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disulfoxide
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葛子义
刘志洋
彭瑞祥
蒋卫刚
李旺
雷涛
管倩
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Ningbo Institute of Material Technology and Engineering of CAS
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Abstract

本发明提供了一种分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料，具有强吸电子能力的亚砜基，与其他具有给电子特性的基团连接可以构成给体材料，具有优异的电荷传输性能，能够拓宽材料在可见光区的吸收。该材料制备方法简单易行，可用于有机太阳能电池的给体材料，以提高电池器件的效率。

Description

分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料、 其制备方法与应用
技术领域
本发明涉及分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料，能够用于有机太阳能电池技术领域。
背景技术
有机太阳能电池因其质轻、价廉和易柔性大面积制备等优点成为光伏领域的研究热点，其中光敏活性层材料是吸收太阳光转换为电能的主体材料，其特性直接决定了电池器件的性能。
但是，目前有机太阳能电池仍然存在吸收光谱窄、载流子迁移率低、效率较低和稳定性较差等问题，需要发展新的高性能给体材料。
发明内容
本发明提供了一种分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料，其化学结构式如下化学结构式(1)-(8)中的一种：
以上结构式(1)-(8)中，每个结构式彼此独立，每个结构式中的n代表聚合度，优选为1至30000中的自然数；
以上结构式(1)-(8)中，每个结构式中的R彼此独立，分别选自以下基团中的任意一种：
以上结构式(1)-(8)中，每个结构式中的R1彼此独立，分别选自以下基团中的任意一种：
本发明还提供了一种制备上述分子主链中包含苯并二亚砜基团的聚合物或小分子材料的方法，具体如下：
(1)苯并二亚砜吩基受体单元的合成
如下述合成路线，在化合物A和二氯甲烷中滴加双氧水和甲酸，室温搅拌，发生氧化反应，反应结束后去除甲酸，用二氯甲烷萃取出产物，干燥，过硅胶柱，得到苯并二亚砜吩基受体单元B；
作为优选，反应结束后采用饱和的碳酸氢钠溶液去除甲酸。
作为优选，采用硫酸镁干燥。
(2)将其他化合物与苯并二亚砜吩基受体单元B在氮气保护下，加入催化剂发生聚合反应，使苯并二亚砜吩基团连接在分子主链中，得到聚合物；或者，将化合物与苯并二亚砜吩基受体单元B在氮气以及催化剂存在条件下发生偶联反应，使苯并二亚砜吩基团连接在分子主链中，得到小分子材料。
作为优选，所述催化剂为三(二亚苄基丙酮)二钯，配体为三苯基膦。
本发明提供的聚合物或小分子材料中包含苯并二亚砜基团，具有强吸电子能力的砜基或亚砜基，与其他具有给电子特性的基团连接可以构成给体材料，具有优异的电荷传输性能，能够拓宽材料在可见光区的吸收。而这些性能正是作为有机太阳能电池的给体材料所需要的，因此作为有机太阳能电池的给体材料时具有高的电荷传输速率和宽的吸收光谱等优点，具有如下有益效果：
(1)本发明提供的聚合物或小分子材料中包含苯并二亚砜基团可作为有机太阳能电池的给体材料，该有机太阳能电池的结构如图1所示，包括基底阳极1、位于基底表面的阳极修饰层2、位于阳极修饰层表面的给体材料与受体材料的混合活性层3，位于混合活性层表面的阴极修饰层4，以及阴极5。其中给体材料用于吸光，将太阳光转换为电能，其材料选用本发明的分子主链中包含苯并二亚砜基团的聚合物或小分子材料。受体材料用于传输电子，可以是富勒烯衍生物受体材料或非富勒烯有机小分子材料等。阳极用于传输空穴，主要为氧化铟锡导电玻璃。阴极用于传输电子，主要为铝电极。阳极修饰层用于传输空穴，减少传输的能量损失和提高界面欧姆接触，主要为PEDOT:PSS。阴极修饰层用于传输电子，减少传输的能量损失和提高界面欧姆接触，主要为钙或镁等。
(2)本发明中可以选择不同的侧链基团和主链单元，以提高分子的共平面性，增强给体材料的摩尔吸收系数，增加材料的载流子迁移率，从而提高电池器件的效率。
(3)本发明提供的制备方法简单易行，操作温和，原料廉价，易于纯化，利于大规模制备。
附图说明
图1是太阳能电池的结构示意图，其中本发明提供的包含苯并二砜吩基团的聚合物或小分子材料作为给体材料；
图2是本发明实施例1中制得的苯并二亚砜吩基受体单元的质谱。
具体实施方式
下面结合实施例对本发明作进一步详细描述，需要指出的是，以下所述实施例旨在便于对本发明的理解，而对其不起任何限定作用。
图1中的附图标记为：1-基底阳极，2-阳极修饰层，3-给体材料与受体材料的混合活性层，4-阴极修饰层，5-阴极。
实施例1：
本实施例中，聚合物结构式如下：
该聚合物的制备包括如下步骤：
(1)苯并二亚砜吩基受体单元的制备
在圆口烧瓶中加入0.3g化合物1和20mL二氯甲烷，将烧瓶放在低温浴中冷却到5摄氏度，滴加浓度为30％的10mL双氧水和15mL甲酸，搅拌反应12小时。反应结束后，滴加饱和的碳酸氢钠溶液去除甲酸，用二氯甲烷萃取出产物后，用硫酸镁干燥。旋干后过硅胶柱得到淡黄色产物2，质量为0.16g，产率为51％。1H-NMR(400MHz,CDCl3):δ7.39(d,2H),6.71(d,2H),4.41(t,4H),2.0-1.81(m,4H),1.55-1.45(m,4H),1.39-1.33(m,8H),0.89(t,6H)。计算的分子量为C26H36Br2O4S2,634.04，实际质谱如下
(2)聚合物给体材料的制备
在三颈瓶中加入0.1g化合物4、0.070g化合物2和10mL甲苯，置换三次氮气，加入4mg催化剂三(二亚苄基丙酮)二钯和4.63mg三苯基膦，再置换三次氮气，在回流下反应24小时。反应结束后出产物进行索氏提取，分别使用甲醇、丙酮和正己烷作溶剂，最后用甲苯得到66mg聚合产物6，产率36％。
1H-NMR(400MHz,CDCl3):δ7.56(d,2H),7.1(d,2H),6.6(d,2H),6.5(d,2H),4.1-3.7(m,4H),2.5-2.3(m,4H),1.9-1.8(m,4H),1.33-1.25(m,32H),1-0.95(m,24H).
上述制得的聚合物可用于有机太阳能电池中作为给体材料。该有机太阳能电池的结构如图1所示，其中阳极采用氧化铟锡导电玻璃，在上面旋涂一层阳极修饰层PEDOT:PSS聚合物导电膜，120度处理20分钟后，受体材料为富勒烯衍生物，旋涂给体材料和受体材料的混合溶液作为活性层，干燥30分钟后，在热蒸镀仪里真空度为10-6mbar以下蒸镀20nm金属钙与100nm阴极修饰层和铝阴极，通过掩膜版控制蒸镀金属阴极的面积。
实施例2：
本实施例中，聚合物结构式如下：
该聚合物的制备包括如下步骤：
在三颈瓶中加入0.1g化合物2、0.064g 2,5-三甲基锡噻吩和10mL甲苯，置换三次氮气，加入4mg催化剂三(二亚苄基丙酮)二钯和4.63mg三苯基膦，再置换三次氮气，在回流下反应24小时。反应结束后出产物进行索氏提取，分别使用甲醇、丙酮和正己烷作溶剂，最后用甲苯得到聚合产物50mg，产率57％。
1H-NMR(400MHz,CDCl3):δ7.3-7.2(m,2H),7.0-6.8(m,2H),4.0-3.78(m,4H),2.0-1.9(m,2H),1.3-1.2(m,16H),1-0.9(m,12H)。
上述制得的聚合物可用于有机太阳能电池中作为给体材料。该有机太阳能电池的结构如图1所示，其中阳极采用氧化铟锡导电玻璃，在上面旋涂一层阳极修饰层PEDOT:PSS聚合物导电膜，120度处理20分钟后，受体材料为富勒烯衍生物，旋涂给体材料和受体材料的混合溶液作为活性层，干燥30分钟后，在热蒸镀仪里真空度为10-6mbar以下蒸镀20nm金属钙与100nm阴极修饰层和铝阴极，通过掩膜版控制蒸镀金属阴极的面积。
以上所述的实施例对本发明的技术方案进行了详细说明，应理解的是以上所述仅为本发明的具体实施例，并不用于限制本发明，凡在本发明的原则范围内所做的任何修改、补充或类似方式替代等，均应包含在本发明的保护范围之内。

Claims (10)

1.分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料，其化学结构式如下化学结构式(1)‐(8)中的一种：
以上结构式(1)‐(8)中，每个结构式彼此独立，每个结构式中的n代表聚合度；
以上结构式(1)‐(8)中，每个结构式中的R彼此独立，分别选自以下基团中的任意一种：
-O-C6H13；-O-C12H25；-C6H13；-C12H25；
以上结构式(1)‐(8)中，每个结构式中的R1彼此独立，分别选自
以下基团中的任意一种：
2.如权利要求1所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料，其特征是：聚合度n是1至30000中的自然数。
3.如权利要求1或2所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料的制备方法，其特征是：包括如下步骤：
(1)苯并二亚砜吩基受体单元的合成
如下述合成路线，在化合物A和二氯甲烷中滴加双氧水和甲酸，室温搅拌，发生氧化反应，反应结束后去除甲酸，用二氯甲烷萃取出产物，干燥，过硅胶柱，得到苯并二亚砜吩基受体单元B；
(2)将其他化合物与苯并二亚砜吩基受体单元B在氮气保护下，加入催化剂发生聚合反应，使苯并二亚砜吩基团连接在分子主链中，得到聚合物；或者，将化合物与苯并二亚砜吩基受体单元B在氮气以及催化剂存在条件下发生偶联反应，使苯并二亚砜吩基团连接在分子主链中，得到小分子材料。
4.如权利要求3所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料的制备方法，其特征是：所述的步骤(1)中，反应结束后采用饱和的碳酸氢钠溶液去除甲酸。
5.如权利要求3所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料的制备方法，其特征是：所述的步骤(1)中，采用硫酸镁干燥。
6.如权利要求3所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料的制备方法，其特征是：所述的步骤(2)中，催化剂为三(二亚苄基丙酮)二钯，配体为三苯基膦。
7.如权利要求1或2所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料作为有机太阳能电池的给体材料的应用。
8.如权利要求7所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料作为有机太阳能电池的给体材料的应用，受体材料是富勒烯衍生物受体材料或非富勒烯有机小分子材料。
9.如权利要求7所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料作为有机太阳能电池的给体材料的应用，阳极修饰层为PEDOT:PSS，阴极修饰层为钙或镁。
10.如权利要求7所述的分子主链中包含苯并二亚砜吩基团的聚合物或小分子材料作为有机太阳能电池的给体材料的应用，阳极为氧化铟锡导电玻璃；阴极为铝电极。
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