有机化学 ›› 2020, Vol. 40 ›› Issue (4): 831-855.DOI: 10.6023/cjoc201910042 上一篇    下一篇

综述与进展

C—H键直接芳基化制备共轭功能材料及其器件应用

刘慧a, 张小凤a, 程敬招a, 叶东鼐a, 陈龙a,b, 温和瑞a, 刘诗咏a   

  1. a 江西理工大学材料冶金化学学部 江西赣州 341000;
    b 天津大学化学系 天津 300072
  • 收稿日期:2019-10-31 修回日期:2019-11-29 发布日期:2019-12-27
  • 通讯作者: 刘诗咏 E-mail:chelsy@zju.edu.cn
  • 基金资助:
    国家自然科学基金(No.21374075)资助项目.

Direct C—H Arylation-Derived π-Conjugated Functional Materials for Device Applications

Liu Huia, Zhang Xiaofenga, Cheng Jingzhaoa, Ye Dongnaia, Chen Longa,b, Wen Heruia, Liu Shiyonga   

  1. a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou Jiangxi 341000;
    b Department of Chemistry, Tianjin University, Tianjin 300072
  • Received:2019-10-31 Revised:2019-11-29 Published:2019-12-27
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21374075).

π-共轭光电聚合物及小分子,由于其成本低、质量轻、可溶液加工性以及结构与性能的丰富可调控性,已成为新一代光电功能器件重要的半导体材料.C—B/C—X及C—Sn/C—X键Suzuki及Stille偶联是有机半导体材料中sp2-C—C键最常用的构建策略.然而,传统的C—C键偶联需要对反应底物进行预官能团化,合成步骤繁琐,且伴随有毒副产物的生成.直接芳基化反应利用C—H/C—X键偶联构建sp2-C—C键,反应底物不涉及有机金属试剂,具有良好的原子及步骤经济性,在有机光电材料的高效合成及实际应用领域拥有巨大的潜力,因而成为人们关注的焦点.针对直接芳基化法制备有机共轭功能材料的器件应用研究进行了总结综述,分别就有机太阳能电池、场效应晶体管、染料敏化和钙钛矿电池、有机发光二极管及锂电池进行分类讨论,系统介绍了该领域的研究进展,并对今后发展进行了展望.

关键词: C—H键直接芳基化, 共轭功能材料, 原子及步骤经济性, 有机太阳能电池, 有机场效应晶体管, 有机光电器件

Organic π-conjugated polymers and small molecules, featured by low cost, light weight, solution processibility as well as finely adjustable structure and properties, have become kinds of fundamental semiconductor materials for next generation of optoelectric devices. The C——B/C——X Suzuki and C——Sn/C——X Stille couplings have become the most widely used strategy for the construction of sp2-C——C bonds involved in organic semiconductor materials. However, these traditional C——C coupling reactions usually involve prefunctionalization of subtrates and multipe synthetic steps, along with toxic by-products. In recent years, the direct C——H arylation reaction (C——H/C——X coupling) for the construction of sp2-C——C bonds and the synthesis of organic π-conjugated materials, featured by the simplicity without use of organometallic precursors, high atom- and step-econogy and low cost, has attracted extensive attention from researchers, due to its great potential for pratical applictions. The C——H/C——X direct arylation coupling has great potential in the efficient synthesis and practical application of organic optoelectric materials. Herein, an overview of recent developments in direct C——H arylation for the synthesis of organic conjugated functional materials used in device applications is provided, including organic photovoltaics (OPV), organic field effect transistor (OFET), dye-sensitized solar cell (DSSC), perovskite cells (PSC), organic light emitting diode (OLED) and lithium rattery, etc. The advantages, challenges as well as the future developments in the area of direct C——H arylation are also discussed and commented.

Key words: direct C—H arylation, π-conjugated functional materials, atom- and step-economic synthesis, organic solar cells, organic field effect transitors, organic optoelectric devices