Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 157-169.DOI: 10.6023/cjoc201808034 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞 有机氟化学合辑



梁龙a,b, 刘丽娜b, 陈学强b, 项宣b, 凌君c, 鲁郑全a, 李靖靖a, 李维实a,b   

  1. a 郑州工程技术学院 郑州高性能有机材料工程研究中心 郑州 450044;
    b 中国科学院上海有机化学研究所 有机功能分子合成与组装重点实验室 上海 200032;
    c 浙江大学高分子科学与工程学系 杭州 320027
  • 收稿日期:2018-08-28 修回日期:2018-10-25 发布日期:2018-11-12
  • 通讯作者: 李维实
  • 基金资助:


Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

Liang Longa,b, Liu Li-Nab, Chen Xue-Qiangb, Xiang Xuanb, Ling Junc, Lu Zheng-Quana, Li Jing-Jinga, Li Wei-Shia,b   

  1. a Zhengzhou Engineering Research Center for High Performance Organic Functional Materials, Zhengzhou Institute of Technology, Zhengzhou 450044;
    b Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 320027
  • Received:2018-08-28 Revised:2018-10-25 Published:2018-11-12
  • Contact: 10.6023/cjoc201808034
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21474129, 21674125, 51761145043), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), the Science and Technology Open Cooperation Projects of Henan Province (Nos. 162106000018, 172106000067) and the Zhengzhou Institute of Technology.

Fluorination on conjugated components is one of popular strategies to modify organic optoelectronic materials. Following the research of a benzodithiophene/benzothiadiazole ADA-type optoelectronic molecule, two benzothiadiazole (BT) units were fluorinated with different numbers and positions, and the change in basic properties and performances for field-effect transistors and organic solar cells was investigated. It was found that when the F-substitution number increases, the molecule enhances thermal stability, decreases solubility, lowers HOMO and LUMO energy levels, but almost does not alter light absorption range. Furthermore, investigations on organic field-effect transistors found the molecular hole mobility reduces with only one F-substituent at outer position of BT units, while increases up to 0.27 cm2·V-1·s-1 with two F substituents on BT units. However, when these materials are applied in organic solar cells, the fluorinated ones enhance open-circuit voltage, but deteriorate active layer morphology, finally leading to decrease in short-circuit current and device efficiency.

Key words: organic optoelectronic materials, fluorination effect, organic field-effect transistors, organic solar cells