C—H键直接芳基化制备共轭功能材料及其器件应用

doi:10.6023/cjoc201910042

摘要/Abstract

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

引用此文

刘慧, 张小凤, 程敬招, 叶东鼐, 陈龙, 温和瑞, 刘诗咏. C—H键直接芳基化制备共轭功能材料及其器件应用[J]. 有机化学, 2020, 40(4): 831-855.

Liu Hui, Zhang Xiaofeng, Cheng Jingzhao, Ye Dongnai, Chen Long, Wen Herui, Liu Shiyong. Direct C—H Arylation-Derived π-Conjugated Functional Materials for Device Applications[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 831-855.

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