可溶液加工p-n多臂结构共轭分子的设计合成与应用

doi:10.6023/cjoc201405016

有机化学 ›› 2014, Vol. 34 ›› Issue (10): 2027-2034.DOI: 10.6023/cjoc201405016 上一篇下一篇

研究论文

可溶液加工p-n多臂结构共轭分子的设计合成与应用

范晓春, 王芳, 李祥春, 陈垚, 赖文勇, 黄维

南京邮电大学信息材料与纳米技术研究院有机电子与信息显示国家重点实验室培育基地南京 210023

收稿日期:2014-05-10 修回日期:2014-06-01 发布日期:2014-06-16
通讯作者: 赖文勇, 黄维 E-mail:iamwylai@njupt.edu.cn;iamwhuang@njupt.edu.cn
基金资助:
国家重点基础研究发展计划（973计划，No. 2014CB648300）、国家自然科学基金（Nos. 20904024，51173081，61136003，61106036）、江苏省自然科学基金（No. BK20130037，BK2011760）、教育部新世纪优秀人才（No. NCET-13-0872）、教育部博士点基金博导类（No. 20133223110008）、教育部创新团队（No. IRT1148）、江苏高校优势学科建设工程（PAPD）、江苏省六大人才高峰（No. 2012XCL035）和江苏省“青蓝工程”资助项目.

Solution-Processable Star-Shaped Conjugated Molecules with Multiple p-n Branches：Synthesis and Photovoltaic Properties

Fan Xiaochun, Wang Fang, Li Xiangchun, Chen Yao, Lai Wenyong, Huang Wei

Key Laboratory for Organic Electronics & Information Displays KLOEID and Institute of Advanced Materials IAM, Nanjing University of Posts & Telecommunications, Nanjing 210023

Received:2014-05-10 Revised:2014-06-01 Published:2014-06-16
Supported by:
Project supported by the National Key Basic Research Program of China (973 Program, No. 2014CB648300), the National Natural Science Foundation of China (Nos. 20904024, 51173081, 61136003, 61106036), the Natural Science Foundation of Jiangsu Province (Nos. BK20130037, BK2011760), the Ministry of Education of China (Nos. NCET-13-0872, 20133223110008, IRT1148), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the Six Talent Plan (No. 2012XCL035), the Qing Lan Project of Jiangsu Province.

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1. 可溶液加工p-n多臂结构共轭分子的设计合成与应用.PDF(2669KB)

摘要/Abstract

设计合成了两种以p型苯基咔唑为核，n型苯并噻二唑衍生物为臂的p-n多臂结构共轭分子S1和S2. 通过¹H NMR，¹³C NMR，GC-MS/MALDI-TOF等表征了其化学结构，研究了其光物理性质、热力学性质、电化学性质及其电子结构等，并作为活性材料应用于制备有机太阳能电池器件. 实验结果表明所得的p-n多臂结构共轭分子表现出良好的溶液加工性、较宽的光谱吸收、较窄的能隙和较高的开路电压等特性.

关键词: p-n共轭分子, 多臂结构分子, 可溶液加工, 光电转换

Well-defined π conjugated star-shaped molecules have attracted much research interest in the field of organic electronics, due to their good monodispersity, high purity, excellent reproducibility, facile functionalization, interesting two/three-dimensional architecture and potential intriguing isotropic optoelectronic properties. Here two new p-n type star-shaped conjugated molecules, S1 and S2, with phenylcarbazole as core and benzothiodiazole derivatives as arms, were designed and synthesized. They are readily soluble in common organic solvents. The structures of the intermediates and resulting molecules were adequately confirmed by ¹H NMR, ¹³C NMR, MALDI-TOF, and elemental analysis. S1 and S2 exhibited good thermal stability according to thermal gravimetric analysis; cyclic voltammetry revealed low-lying HOMO and LUMO energy levels as well as narrow band gaps. The HOMO/LUMO energy levels and band gaps could be facilely modulated by varying the content and sequence of p and/or n type moieties. With incorporating 3-hexylthiophene π bridge unit, S2 film shows a broad absorption band from 300 nm to 650 nm in films with absorption edge red-shifted by ca. 38 nm in comparison with that of S1. Additionally, S2 possessed amorphous properties, while S1 exhibited crystalline properties in powder. Density functional theory (DFT) calculation was also conducted to further understand the electronic properties. Solution-processed organic solar cells based on a blend of S1 and PC₇₀BM (1:3, w/w) exhibited power conversion efficiency (PCE) of 0.34% with a short circuit current density (J_sc) of 1.5 mA/cm² and an open circuit voltage (V_oc) of 0.83 V under the illumination of AM1.5, 100 mW/cm². Improved performance was achieved for S2 with PCE of 0.5%, J_sc of 1.85 mA/cm², and a high V_oc of 1.0 V under identical conditions.

Key words: p-n type conjugated molecule, star-shaped molecule, solution processable, organic photovoltaic

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范晓春, 王芳, 李祥春, 陈垚, 赖文勇, 黄维. 可溶液加工p-n多臂结构共轭分子的设计合成与应用[J]. 有机化学, 2014, 34(10): 2027-2034.

Fan Xiaochun, Wang Fang, Li Xiangchun, Chen Yao, Lai Wenyong, Huang Wei. Solution-Processable Star-Shaped Conjugated Molecules with Multiple p-n Branches：Synthesis and Photovoltaic Properties[J]. Chin. J. Org. Chem., 2014, 34(10): 2027-2034.

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可溶液加工p-n多臂结构共轭分子的设计合成与应用

Solution-Processable Star-Shaped Conjugated Molecules with Multiple p-n Branches：Synthesis and Photovoltaic Properties

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