CN111205307A - 一种噻吩并苯并噻二唑二酮有机化合物、其制备方法与应用 - Google Patents
一种噻吩并苯并噻二唑二酮有机化合物、其制备方法与应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于有机化合物技术领域,具体涉及一种噻吩并苯并噻二唑二酮有机化合物、其制备方法与应用。
背景技术
有机太阳能电池由于其在低成本、易于大面积、柔性器件制备等上的巨大潜力,近几十年来备受关注。经过二十多年的发展,目前单层本体异质结的有机太阳能电池的效率已经达到16%以上,在未来将有更广大的前景。
发明内容
本发明提供一种噻吩并苯并噻二唑二酮有机化合物,具有带隙窄、平面性好,以及刚性强等特点,通过聚合反应可作为有机光电活性给体材料。
该有机化合物的结构式如下:
其中,R1为C1-C20烷基以及C1-C20的烷氧基中的一种;Ar为以下基团之一:
噻吩基团、噻吩衍生物基团、并二噻吩基团、并二噻吩衍生物基团、并三噻吩基、并三噻吩衍生物基团、苯并二噻吩基团、苯并二噻吩衍生物基团、吡咯并二噻吩基团、吡咯并二噻吩衍生物基团、戊烷并二噻吩基团、戊烷并二噻吩衍生物基团。
上述衍生物基团包括但不限于如下结构式(虚线为连接位置):
上述各结构式中,R2为C1-C20的烷基,C1-C20的烷氧基、羰基、酯基、苯基、取代苯基、噻吩基、或取代噻吩基(C1-C20中含有羰基、酯基、苯基、取代苯基、噻吩基、取代噻吩基)。
本发明还提供一种制备上述苯并噻二唑二酮聚合物的方法,包括如下步骤:
(1)采用2,1,3-苯并噻二唑-4,7-二硼酸频那醇酯A和化合物B通过Suzuki偶联反应,得到中间体C,反应路线如下所示:
(2)中间体C与NBS反应,得到如下化合物D:
(3)化合物D和化合物E通过Stille偶联反应得到化合物F,反应路线如下所示:
(4)化合物F先进行水解反应,提纯后再和NBS(N-溴代丁二酰亚胺)反应得到如下化合物G:
(5)化合物G通过Friedel-Crafts反应得到如下所示的噻吩并苯并噻二唑二酮聚合物:
本发明在聚合物中引入醌式共轭结构单元,具有如下有益效果:
(1)该有机化合物具有良好的溶解性,易于加工成膜,经提纯后具有高的化学纯度;
(2)该有机化合物中引入二酮,增加了有机化合物分子的刚性和平面性;
(3)该有机化合物可与含锡单体化合物,例如PDBT、PDBT-2F、PDBT-2Cl等发生锡溴偶联聚合反应得到聚合物,该聚合物可作为有机光电活性给体材料,通过增长给体单元的π-π共轭长度使π-电子更有利于沿整个聚合物骨架分布,有利于载流子的迁移,与常用受体材料,例如IDIC、ITIC、Y6等有较好的能级匹配。
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。
下述实施例中的所述试验方法,若无特殊说明,均为常规方法;所述材料和试剂,若无特殊说明,均可从商业途径获得。
实施例1:
本实施例中,噻吩并苯并噻二唑二酮SM1的化学结构如下:
该噻吩并苯并噻二唑二酮SM1的制备方法包括如下步骤:
(1)采用2,1,3-苯并噻二唑-4,7-二硼酸频那醇酯A和化合物B通过Suzuki偶联反应,得到中间体C,反应路线如下所示:
具体过程是:在三口瓶中加入化合物A和化合物B,然后加入中和剂碳酸钾、少量水和催化剂,催化剂为四三苯基膦钯,催化剂的加入量为化合物A的摩尔量的5%,化合物A和化合物B的摩尔比为1:2.3;再置换三次氮气,最后加入甲苯,在回流下反应18小时;反应结束后用旋蒸仪抽走溶剂,然后用三氯甲烷和水萃取,萃取后用无水硫酸钠干燥;旋干后,用石油醚过硅胶柱得到黄色油状物化合物C。
(2)中间体C与NBS反应,得到如下化合物D:
具体过程是:先将化合物C和N-溴代丁二酰亚胺在冰浴下反应15小时,再用三氯甲烷和水萃取,萃取后用无水硫酸钠干燥,最后用石油醚过柱得到黄色固体化合物D。
(3)化合物D和化合物E通过Stille偶联反应得到化合物F,反应路线如下所示:
具体过程是:先在三口瓶中加入化合物D和化合物E,再加入四三苯基膦钯作为催化剂,然后抽真空换氮气三次,最后加入甲苯,在回流下反应18小时;反应结束后用旋蒸仪抽走溶剂,然后用三氯甲烷和水萃取,萃取后用无水硫酸钠干燥;旋干后用石油醚过硅胶柱得到化合物F。
(4)化合物F先水解提纯后再和NBS得到如下化合物G:
具体过程是:先将化合物F和氢氧化钠按照摩尔比为1:10加入三口烧瓶中,然后加入少量乙醇,在70℃下反应15小时;反应结束后用三氯甲烷和水萃取,萃取后用无水硫酸钠干燥;旋干后后再投入到三口烧瓶中加入NBS冰浴反应12小时得到化合物G。
(5)通过Friedel-Crafts反应得到噻吩并苯并噻二唑二酮SM1:将化合物G和二氯亚砜溶剂(摩尔比为1:5)加入三口烧瓶中,在80℃反应12小时;反应结束后旋干溶剂,再准备一个将三口烧瓶和恒压滴液漏斗烘干,然后将旋干溶剂的化合物用超干二氯溶解倒入到三口烧瓶中,然后把恒压滴液漏斗组装在三口烧瓶上加入FeCl3,使整个装置抽真空换氮气三次,在三口烧瓶和恒压滴液漏斗中加入少许超干二氯溶剂,然后打开恒压滴液漏斗逐渐滴加到三口烧瓶中,在冰浴下反应15小时;反应结束后用三氯甲烷和水萃取,萃取后用无水硫酸钠干燥;旋干后过硅胶柱,用石油醚过柱,既得到噻吩并苯并噻二唑二酮的单体SM1。
将上述制得的单体SM1与含锡单体PDBT-2F发生锡溴偶联聚合反应得到聚合物,反应路线如下:
具体过程是:在25mL的两口瓶中,单体SM1和采用商业化材料PDBT-2F单体按照摩尔比1:1溶解在超干燥的氯苯(10mL)中,在氦气氛围循环抽放气除氧后,加入四三苯基磷钯并将混合物在120℃下避光搅拌12小时,反应结束后冷却至室温,加入到色谱纯甲醇中析出絮状物,收集固体在索氏提取器中。随后依次用甲醇,正己烷,氯仿抽提至无色。通过旋转蒸发仪旋干大部分溶剂后,再用色谱纯甲醇沉降,收集固体后真空干燥得到黑色聚合物SM2,产率85%。
将该聚合物SM2应用于太阳能电池。采用商业化的IDIC受体材料,按照ITO/PEDOT:PSS/SM2:IDIC/PDINO/Al制作太阳能电池。其中,活性层材料为SM2与IDIC,按照质量比SM2:IDIC为1:0.7混合在溶剂中,溶剂可以选用甲苯、氯苯、二氯苯和氯仿等,再加入添加剂,添加剂可以选用氯萘、1,8-二碘辛烷等,制得活性层溶液。使用匀胶机在ITO表面旋涂界面修饰层(PEDOT:PSS),然后将活性层溶液旋涂在界面修饰层表面,旋涂需要在无水无氧的手套箱中,通过控制旋涂的转速调节活性层的厚度,厚度对于器件的性能有很大影响,一般控制活性层厚度为100nm左右。在活性层表面涂覆PDINO之后放在加热台上,以一定的温度加热,然后进行蒸镀电极Al,最后取出做好的电池。
其中IDIC结构如下所示:
实施例2:
本实施例中,噻吩并苯并噻二唑二酮SM1的化学结构与实施例1相同,制备方法与实施例相同。
本实施例中,将SM1通过聚合反应得到SM2,SM2的制备过程与实施例1相同。
本实施例中,将该聚合物SM2应用于太阳能电池。太阳能电池的结构和制备方法与实施例1基本相同,所不同的是活性层材料为PM6、Y6与SM2,按照质量比PM6:Y6:SM2为1:1:0.7混合在溶剂中。
对实施例1与实施例2中的太阳能电池的性能参数进行测试,测试结果如下:
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 (7)
4.一种聚合物,其特征是:如权利要求1或2所述的有机化合物与含锡单体发生锡溴偶联聚合反应得到。
5.如权利要求4所述的聚合物,其特征是:所述含锡单体包括PDBT、PDBT-2F、PDBT-2Cl。
6.如权利要求4所述的聚合物作为有机光电活性给体材料的应用。
7.一种太阳能电池,包括活性层,所述活性层由活性给体材料与活性受体材料,所述活性给体材料是权利要求4所述的聚合物。
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