CN111187398A - 一种吲哚二酮类似物聚合物、制备方法及其应用 - Google Patents
一种吲哚二酮类似物聚合物、制备方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种吲哚二酮类似物聚合物、制备方法及其应用，所述聚合物的Ⅰ型和Ⅱ型如下所表示：
Description
技术领域
本发明涉及有机半导体合成技术领域，具体设计吲哚二酮类似物新型共轭稠环材料的制备方法及性能。
背景技术
吲哚二酮衍生物是一类非常重要有机半导体材料。在有机半导体方向有着十分重要的应用前景，包括有机发光二极管(OLED)、有机场效应晶体管(OFET)等应用。
发明内容
本发明的目的在于提供一种新型的、稳定的、溶解性好，合成方法简单的共轭稠环的吲哚二酮类似物聚合物。
为了实现上述目的，本发明采用如下技术方案：
一种吲哚二酮类似物聚合物，所述聚合物的Ⅰ型和Ⅱ型如下所表示：
Ⅰ型：
Ⅱ型：
其中，Ⅰ型和Ⅱ型中的
可为
R为支链或者直链烷烃。
优选地，所述化学结构通式如下所示：
其中，R为支链或者直链烷烃。
本发明还提供一种吲哚二酮类似物聚合物的制备方法，所述方法包括如下步骤：
S1将1当量稠环二醛与1当量的3,8-双(2-R烷基链)-1,3,6,8-四氢吲哚[7,6g]吲哚-2,7-二酮加入到微波管中；
S2然后加入对甲苯磺酸、甲苯，加热至回流，反应2h-24h；
S3将得到的溶液先沉降，再通过索式提取提纯之后即可得到聚合物。
需要说明的是，其反应方程式为：
其中，AR处为噻吩类稠环化合物，R为直链、支链烷基链的一种。
本发明或获得聚合物的最大吸收波长在可见光领域，在有机场效应晶体管、有机太阳能电池的都具有应用前景。
本发明有益效果在于：
1、本发明的吲哚二酮类似物聚合物合成方法简单，具有良好的溶解性和稳定性。
2、相比于其他的吲哚二酮类似物聚合物，本发明的合成方法具有较高的产率。
3、最大吸收波长在可见光领域，在有机场效应晶体管(OFET)、有机太阳能电池(OPV)领域具有潜在的应用前景。
附图说明
图1为实施例1中化合物A的CV图。
图2为实施例2中化合物B的CV图。
图3为实施例3中化合物C的CV图。
图4为实施例4中化合物D的CV图。
图5为实施例5中化合物E的CV图。
图6为实施例6中化合物F的CV图。
图7为实施例1中的化合物A，实施例2中的化合物B，实施例3中的化合物C，实施例4中的化合物D，实施例5中的化合物E的紫外吸收图。
图8为实施例6中的化合物F的紫外吸收图。
具体实施方式
以下将结合附图对本发明作进一步的描述，需要说明的是，以下实施例以本技术方案为前提，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并不限于本实施例。
需要说明的是，本发明所用试剂和材料均为市购。进一步的，本发明采用了瑞士Bruker公司生产的AVANCE III 400M型液体核磁共振谱仪来检测产物的1H NMR，溶剂为氘代氯仿(CDCl3)，四甲基硅烷(TMS)为内标。利用Shimadzu公司的UV-3600型紫外可见分光光度计来测定产物的紫外吸收光谱，采用1×1cm的石英比色皿作为样品池,采用上海辰华仪器有限公司的CHI620E电化学分析仪。
实施例1
将17.78mg化合物Ⅰ，23.85mg化合物Ⅲ加入微波管，加入1.17mgPTSA，通过抽充氮气半个小时，加入0.7ml甲苯，反应20h，通过索氏提取装置得到化合物A，图1为实施例1中化合物A的CV图，图7为实施例1中的化合物A紫外吸收图，空穴迁移率为9.33E-03μ(cm2v-1s-1)。
其中化合物Ⅰ通过现有文献记载的方法制得，具体是以下文献：
1、N.M.Randell,P.C.Boutin,T.L.Kelly,J.Mater.Chem.A.2016.4,6940-6945。
2、Y.Jiang,Y.Gao,H.Tian,J.Ding,D.Yan,Y.Geng,F.Wang,Macromolecules,2016,49,2135-2144。
实施例2
将33.02mg化合物Ⅰ，5.51mg化合物Ⅳ加入微波管，加入1.57mgPTSA，通过抽充氮气半个小时，加入0.5ml甲苯，反应24h，通过索氏提取装置得到化合B，图2为实施例2中化合物B的CV图，图7为实施例2中的化合物B紫外吸收图，空穴迁移率为4.55E-05μ(cm2v-1s-1)。
其中化合物Ⅰ获得途径与实施例1相同。
实施例3
将30mg化合物Ⅰ，8.32mg化合物Ⅴ加入微波管，加入1.42mg PTSA，通过抽充氮气半个小时，加入0.7ml甲苯，反应4h，通过索氏提取装置得到化合物C，图3为实施例3中化合物C的CV图，图7为实施例3中的化合物C的紫外吸收图，空穴迁移率为2.51E-02μ(cm2v-1s-1)。
其中化合物Ⅰ获得途径与实施例1相同。
实施例4
将30mg化合物Ⅰ，9.31mg化合物VI加入微波管，加入1.42mgPTSA，通过抽充氮气半个小时，加入0.7ml甲苯，反应16h，通过索氏提取装置得到化合D，图4为实施例4中化合物D的CV图，图7为实施例4中的化合物D的紫外吸收图，空穴迁移率为1.2E-03μ(cm2v-1s-1)。
其中化合物Ⅰ获得途径与实施例1相同。
实施例5
将30mg化合物Ⅰ，7.365mg化合物VII加入微波管，加入1.44mgPTSA，通过抽充氮气半个小时，加入0.8ml甲苯，反应2h，通过索氏提取装置得到化合E，图5为实施例5中化合物E的CV图，空穴迁移率为9.51E-02μ(cm2v-1s-1)，图7为实例5中的化合物E紫外吸收图。
其中化合物Ⅰ获得途径与实施例1相同。
实施例6
将35mg化合物Ⅱ，8.62mg化合物Ⅲ加入微波管，加入1.62mg PTSA，通过抽充氮气半个小时，加入0.8ml甲苯，反应12h，通过索氏提取装置得到化合物F，图6为实施例6中化合物F的CV图，图8为实施例6中的化合物F的紫外吸收图。
其中化合物Ⅰ通过现有的文献制得，具体是以下文献：
P Singla,N.V.Steerteghem,N.Kaur,A.Z.Ashar,P.Kaur,K Clays,K.S.Narayancand K Singh.J.Mater.Chem.C,2017,5,697-708
对于本领域的技术人员来说，可以根据以上的技术方案和构思，给出各种相应的改变和变形，而所有的这些改变和变形，都应该包括在本发明权利要求的保护范围之内。
Claims (5)
1.一种吲哚二酮类似物聚合物，其特征在于，所述聚合物的Ⅰ型和Ⅱ型如下所表示：
Ⅰ型：
Ⅱ型：
其中，Ⅰ型和Ⅱ型中的
可为
R为支链或者直链烷烃。
2.根据权利要求1所述的吲哚二酮类似物聚合物，其特征在于，所述化学结构通式如下所示：
其中，R为支链或者直链烷烃。
3.一种根据权利要求1所述的吲哚二酮类似物聚合物的制备方法，其特征在于，所述方法包括如下步骤：
S1将1当量稠环二醛与1当量的3,8-双(2-R烷基链)-1,3,6,8-四氢吲哚[7,6g]吲哚-2,7-二酮加入到微波管中；
S2然后加入对甲苯磺酸、甲苯，加热至回流，反应2h-24h；
S3将得到的溶液先沉降，再通过索式提取提纯之后即可得到聚合物。
4.根据权利要求3所述的吲哚二酮类似物聚合物的制备方法，其特征在于，反应方程式为：
其中，AR处为噻吩类稠环化合物，R为直链、支链烷基链的一种。
5.一种根据权利要求3所制备获得的吲哚二酮类似物聚合物，其特征在于，所述聚合物的最大吸收波长在可见光领域，在有机场效应晶体管、有机太阳能电池的应用。
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| CN104193971A (zh) * | 2014-07-24 | 2014-12-10 | 合肥工业大学 | 一种新型半导体共轭聚合物及其合成方法 |
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| CN104812795A (zh) * | 2012-11-09 | 2015-07-29 | 李玉宁 | 含有稠环的单体、低聚和聚合半导体以及它们的器件 |
| CN104193971A (zh) * | 2014-07-24 | 2014-12-10 | 合肥工业大学 | 一种新型半导体共轭聚合物及其合成方法 |
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