Research Progress in n-type Organic Semiconducting Materials Based on Amides or Imides

doi:10.6023/A22080380

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (12): 1600-1617.DOI: 10.6023/A22080380 Previous Articles Next Articles

Review

酰胺与酰亚胺类n型有机半导体材料的研究进展

李善武^a, 朱陈宇杰^a, 罗尹豪^a, 张亚茹^a, 滕汉明^a, 王宗瑞^a^,^b, 甄永刚^a^,^c^,^*()

^a北京化工大学有机无机复合材料国家重点实验室北京 100029
^b华中科技大学武汉光电国家研究中心武汉 430074
^c华南理工大学发光材料与器件国家重点实验室广州 510640

投稿日期:2022-08-30 发布日期:2022-10-31
通讯作者: 甄永刚

作者简介:

李善武, 北京化工大学材料科学与工程学院2020级本科生, 专业方向为高分子材料.

朱陈宇杰, 北京化工大学材料科学与工程学院2020级本科生, 专业方向为高分子材料.

罗尹豪, 北京化工大学材料科学与工程学院2020级本科生, 专业方向为高分子材料.

张亚茹, 北京化工大学材料科学与工程学院2020级本科生, 专业方向为功能材料.

滕汉明, 北京化工大学材料科学与工程学院2020级本科生, 专业方向为材料科学与工程.

王宗瑞, 北京化工大学材料科学与工程学院副教授/硕士生导师. 于中国科学院化学研究所获得博士学位, 之后在新加坡南洋理工大学进行博士后研究, 2021年加入北京化工大学. 主要研究方向为有机共晶多功能材料的组装及器件、分子功能器件、柔性器件及智能仿生应用研究.

甄永刚, 北京化工大学材料科学与工程学院教授/博导. 于中国科学院化学研究所获得博士学位, 之后在日本东京大学进行博士后研究, 2013年回到中科院化学所工作, 2021年加入北京化工大学. 主要致力于有机/高分子光电功能材料的设计合成、晶体工程、柔性电子及其智能仿生应用研究. 2018年获得国家自然科学基金优秀青年科学基金项目资助, 目前担任Chinese Chemical Letters编委.

基金资助:
中央高校基本科研业务费(buctrc202103); 中央高校基本科研业务费(buctrc202128); 国家自然科学基金(21975263); 国家自然科学基金(22171019); 武汉光电国家研究中心开放基金(2021WNLOKF005); 华南理工大学发光材料与器件国家重点实验室(2022-skllmd-14); 吉林大学超分子结构与材料国家重点实验室(SKLSSM2022036)

Research Progress in n-type Organic Semiconducting Materials Based on Amides or Imides

Shanwu Li^a, Chenyujie Zhu^a, Yinhao Luo^a, Yaru Zhang^a, Hanming Teng^a, Zongrui Wang^a^,^b, Yonggang Zhen^a^,^c()

^aState Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029
^bWuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074
^cState Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640

Received:2022-08-30 Published:2022-10-31
Contact: Yonggang Zhen
About author:
†These authors contributed equally to this work.
Supported by:
Fundamental Research Funds for the Central Universities(buctrc202103); Fundamental Research Funds for the Central Universities(buctrc202128); National Natural Science Foundation of China(21975263); National Natural Science Foundation of China(22171019); Open Project Program of Wuhan National Laboratory for Optoelectronics(2021WNLOKF005); State Key Laboratory of Luminescent Materials and Devices(2022-skllmd-14); State Key Laboratory of Supramolecular Structure and Materials(SKLSSM2022036)

The organic semiconducting materials feature various sources, tailorable chemical structures, low-temperature device fabrication and good compatibility with plastic substrates, largely expanding the functions and applications of electronic devices. However, electron-transporting (n-type) organic semiconductors lag far behind their hole-transporting (p-type) counterpart in terms of molecular diversity, carrier mobility as well as air stability, preventing the development in the ambipolar transistors, p-n junctions and organic complementary circuits. Amidation and imidization of aromatic systems can enhance electron affinity values significantly, thus opening up the possibility to achieve high-performance n-type organic semiconductors. The recent research progress in n-type organic small-molecule and polymeric semiconducting materials including naphthalene diimides, perylene diimides, diketopyrrolopyrroles, isoindigos and other amide/imide derivatives is summarized in this review. From the viewpoint of molecular design, we deeply discuss how the molecular structures alter molecular frontier orbital levels, intermolecular forces, aggregation structures, device stability and electrical characteristics. Finally, we address several key points for further exploration in this field.

Key words: n-type organic semiconductors, amides, imides, molecular design, organic field-effect transistors

Cite this article

Shanwu Li, Chenyujie Zhu, Yinhao Luo, Yaru Zhang, Hanming Teng, Zongrui Wang, Yonggang Zhen. Research Progress in n-type Organic Semiconducting Materials Based on Amides or Imides[J]. Acta Chimica Sinica, 2022, 80(12): 1600-1617.

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Fig. & Tab. 10

Figure 1. Four chemical modifications commonly used in molecular design: lateral modification, longitudinal modification, diagonal modification and heteroatomic substitution

Figure 2. NDI-based n-type small organic semiconductors

Figure 3. PDI-based n-type small organic semiconductors

Figure 4. DPP-based n-type small organic semiconductors

Figure 5. Other amide/imide n-type small organic semiconductors

Figure 6. Several methods for developing n-type polymer semiconductors: (a) design and synthesis of novel acceptor units; (b) replacement by electron-withdrawing groups; (c) backbone engineering[82]. Copyright 2019 Acta Polymerica Sinica

Figure 7. NDI-based n-type polymer organic semiconductors

Figure 8. PDI-based n-type polymer organic semiconductors

Figure 10. IID-based n-type polymer organic semiconductors

Figure 11. Other amide/imide n-type polymer organic semiconductors

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酰胺与酰亚胺类n型有机半导体材料的研究进展

Research Progress in n-type Organic Semiconducting Materials Based on Amides or Imides

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