基于蒽衍生高迁移率发光材料的研究进展

doi:10.7503/cjcu20190650

高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (6): 1179.doi: 10.7503/cjcu20190650

• 庆祝《高等学校化学学报》复刊40周年专栏 • 上一篇下一篇

基于蒽衍生高迁移率发光材料的研究进展

谢子仪^1,⁴,刘单^1,³,张逸寒^1,³,刘情情^1,³,董焕丽^1,^3,^*(),胡文平^1,²

^1. 中国科学院化学研究所, 有机固体院重点实验室, 北京分子科学国家研究中心, 北京 100190
^2. 天津大学理学院, 天津市分子光电科学重点实验室, 天津大学协同创新中心, 天津 300072
^3. 中国科学院大学, 北京 100049
^4. 湘潭大学化学学院, 湘潭 411105

收稿日期:2019-12-11 出版日期:2020-06-10 发布日期:2020-02-17
通讯作者: 董焕丽 E-mail:dhl522@iccas.ac.cn
基金资助:
国家重点研发计划“纳米科技”专项(2017YFA0204503);国家重点研发计划“战略性先进电子材料”专项(2016YFB0401100);国家自然科学基金(51725304);国家自然科学基金(51733004);国家自然科学基金(61890943);国家自然科学基金(91833306);北京分子科学国家研究中心项目(BNLMS-CXXM-202012);中国科学院青年创新促进会项目

Recent Advances on High Mobility Emissive Anthracene-derived Organic Semiconductors ^†

XIE Ziyi^1,⁴,LIU Dan^1,³,ZHANG Yihan^1,³,LIU Qingqing^1,³,DONG Huanli^1,^3,^*(),HU Wenping^1,²

^1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
^2. Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Collaborative Innovation Center of Chemical Science and Engineering, School of Sciences, Tianjin University Tianjin, 300072, China
^3. University of Chinese Academy of Sciences, Beijing 100049, China
^4. College of Chemistry, Xiangtan University, Xiangtan 411105, China

Received:2019-12-11 Online:2020-06-10 Published:2020-02-17
Contact: Huanli DONG E-mail:dhl522@iccas.ac.cn
Supported by:
† National Key Research and Development Project-Nanotechnology Funding, China(2017YFA0204503);National Key Research and Development Project-Strategic Advanced Electronic Materials Funding, China(2016YFB0401100);National Natural Science Foundation of China(51725304);National Natural Science Foundation of China(51733004);National Natural Science Foundation of China(61890943);National Natural Science Foundation of China(91833306);Beijing National Laboratory for Molecular Sciences, China(BNLMS-CXXM-202012);Youth Innovation Promotion Association of the Chinese Academy of Sciences

摘要/Abstract

摘要：

高迁移率发光有机半导体材料是实现有机发光场效应晶体管(OLETs)的重要材料, 但其设计合成面临巨大挑战. 本文综合评述了近年来高迁移率发光材料, 特别是基于蒽的高迁移率发光材料的研究进展, 重点介绍了目前报道的20余种基于蒽的高迁移率发光有机半导体材料, 包括分子的设计策略、相关的光电性能及其在OLETs器件方面的应用研究, 以便为进一步的相关研究提供有意义的指导和借鉴. 本文还对该领域未来发展的挑战、发展方向及机遇进行了简单评述.

关键词: 蒽衍生物, 高迁移率, 强发光, 有机发光场效应晶体管

Abstract:

High mobility emissive organic semiconductors are the important core materials for the realization of organic light-emitting transistors(OLETs). However, it remains a long-standing challenge for developing high mobility emissive organic semiconductors because of the different molecular design requirements as well as their molecular packing in solid state. Recently, significant advance has been achieved in the development of high mobility emissive organic semiconductors, especially for the anthracene-derived high mobility emissive materials, which would lead to the rapid development of this field. In this article, we first give a brief introduction for the significant progress in the whole field, and then focus on special development of high mobility emissive anthracene-derivatives(more than 20 types) along with their molecular structure design, molecular packing and optoelectronic properties as well as their applications in OLETs. Finally, the challenges, development directions and opportunities are discussed. Hopefully, this review would give a valuable guideline for the further research in this field.

Key words: Anthracene derivative, High mobility, Strong solid luminescence, Organic light-emitting transistor

中图分类号:

O625
O649

TrendMD:

谢子仪, 刘单, 张逸寒, 刘情情, 董焕丽, 胡文平. 基于蒽衍生高迁移率发光材料的研究进展. 高等学校化学学报, 2020, 41(6): 1179.

XIE Ziyi, LIU Dan, ZHANG Yihan, LIU Qingqing, DONG Huanli, HU Wenping. Recent Advances on High Mobility Emissive Anthracene-derived Organic Semiconductors ^†. Chem. J. Chinese Universities, 2020, 41(6): 1179.

图/表 10

Fig.1 Chemical structure of anthracene and its derived positions

Fig.2 Chemical structures of 2,6-substituted anthracene derivatives based on C=C bonds HPVAnt: ?PL=20%(TF), 70%(SC); μh=1.5 cm2·V-1·s-1(TF), 2.62 cm2·V-1·s-1(SC); μe=0.13 cm2·V-1·s-1(SC)2,6-DPSAnt: ?PL=14%(SC), μh=0.75 cm2·V-1·s-1(TF). DPEA: ?PL=29.6%(SC), μh=0.66 cm2·V-1·s-1(SC)TF: thin film; SC: single crystals.

Fig.3 Chemical structures of 2,6-substituted anthracene derivatives based on C—C bonds BPTA: ?PL=31%(SC), μh=0.14 cm2·V-1·s-1(SC), μe=0.19 cm2·V-1·s-1(SC); DPA: ?PL=41.2%(SC), 48.4%(Powder), μh=14.8 cm2·V-1·s-1(TF), μh=34 cm2·V-1·s-1(SC); dNaAnt: ?PL=29.2%(SC), μh=12.3 cm2·V-1·s-1(SC); DPy2A: ?PL=50.2%(SC), μh=0.05 cm2·V-1·s-1(TF); DPy3A: ?PL=17.5%(SC), μh=10-5 cm2·V-1·s-1(TF); BEPAnt: ?PL=43%(Solution), μh=3.72 cm2·V-1·s-1(TF); BOPAnt: ?PL=42%(Solution), μh=2.96 cm2·V-1·s-1(TF); BSPAnt: ?PL=52%(Solution), μh=0.12 cm2·V-1·s-1(TF); BDBFAnt: ?PL=49%(TF), μh=3.0 cm2·V-1·s-1(TF); NaAnt: ?PL=40.3%(Powder), μh=1.10 cm2·V-1·s-1(TF); FLAnt: ?PL=15.7%(TF), μh=0.22 cm2·V-1·s-1(TF); 2A: ?PL=13.9%(TF), μh=3.19 cm2·V-1·s-1(TF); Ant-ThPh: ?PL=33.32%(SC), μh=4.7 cm2·V-1·s-1(SC); Ant-Th-Ph: ?PL=36.52%(SC), μh=1.1 cm2·V-1·s-1(SC)

Fig.4 Chemical structures of 9,10-substituted and other anthracene derivatives BPEA: ?PL=29%(SC, α), 32%(SC, β), μh,α=0.73 cm2·V-1·s-1(SC), μe,β<0.01 cm2·V-1·s-1(SC); BDPVA: ?PL=60%(SC), 38%(Film), μh=0.08 cm2·V-1·s-1(SC), μh=0.06 cm2·V-1·s-1(SC); TES-PDA: ?PL=77.3%(SC), μh=1.47 cm2·V-1·s-1(SC); DP-BPEA: ?PL=32%(SC), μh=1.37 cm2·V-1·s-1(SC); DABD: ?PL=3.4%(SC,β), μh=0.25-5 cm2·V-1·s-1(SC, β); 1,5-DPSAnt: ?PL=4%—9%(Solid), μh=0.15 cm2·V-1·s-1(TF)

Fig.5 A histogram summary of optoelectronic property and structure torsion angles of some anthracene-based high mobility emissive organic semiconductors discussed in this article Here the torsion angle data marked by red rhombuses are measured based on their. cif data, while others are directly extracted from the references. a. HPVAnt; b. 2,6-DPSAnt; c. DPEA; d. BPTA; e. DPA; f. dNaAnt; g. BEPAnt; h. BOPAnt; i. BSPAnt; j. DPy2A; k. DPy3A; l. BDBFAnt; m. NaAnt; n. FIAnt; o. 2A; p. Ant-ThPh; q. Ant-Th-Ph; r. BPEA; s. BDPVA; t. TES-DPA; u. DP-BPEA; v. DABD; w. 1,5-DPSAnt.

Fig.6 CIE 1931 coordinates of these reported anthracene-based high mobility emissive organic semiconductors

Fig.7 HOMO and LUMO energy levels of anthracene derivatives discussed in this article Blue: HOMO level; red: LUMO level.

Fig.8 Top-contact OLETs fabricated with HPVAnt[69] (A) Schematic of the biased device; (B) optical image and EL of the biased device; (C) transfer characteristics of the biased device. VDS=-75 V; (D) output characteristics of the biased device. Vg=-75 V(blue), -60 V(teal), -45 V(pink), -30 V(black), -15 V(red)' μ=1.33 cm2·V-1·s-1; on/off ratio=3×107; VT=-24 V. IDS is drain-source current.Copyright 2012, Wiley-VCH.

Fig.9 Electroluminescence performances of DPA-and dNaAnt-based OLETs devices[34] (A) A series of color-coded images for a dNaAnt-OLET extracted from light emission captured by CCD operating under forwards and backwards. The channel length: 28 μm. (B) Output characteristic of light emission position and intensity of the device in(A) versus gate bias sweeping. (C, D) A series of color-coded images of DPA-OLET(C) and dNaAnt-OLET(D) under p- and n-channel operation, respectively. The blue area in(A, C, D) represents the darkest part of a CCD image and the red area is the brightest. The channel length for device(C) and device(D) is 73 and 69 μm, respectively. (E, F) Electroluminescence spectra of DPA OLET(E) and dNaAnt OLET(F).Copyright 2019, Wiley-VCH.

Fig.10 Electroluminescence performances of DPA- and dNaAnt-based OLET devices[34] (A—D) Output characteristic and corresponding light-emitting outputs(A, C), EQE versus Vg(B, D) for DPA-OLETs(A, B) and dNaAnt-OLETs(C, D) within both p- and n-channel regions. (E) A summary map of single-component OLETs reported so far in the literature based on common substrate without additional half-sphere mounted for light collection. Copyright 2019, Wiley-VCH.

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基于蒽衍生高迁移率发光材料的研究进展

Recent Advances on High Mobility Emissive Anthracene-derived Organic Semiconductors ^†

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基于蒽衍生高迁移率发光材料的研究进展

Recent Advances on High Mobility Emissive Anthracene-derived Organic Semiconductors †

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Recent Advances on High Mobility Emissive Anthracene-derived Organic Semiconductors ^†