Yang Zhisheng1,2, Ke Weifang3, Wang Yanxiang2, Huang Liqun2, Zhu Hua4
1.Department of Physics and Electronics,Shangrao Normal University,Shangrao 334001; 2.Department of Materials Science and Engineering,Jingdezhen Ceramic Institute,Jingdezhen 333403; 3.Department of Ceramic Art,Jingdezhen Ceramic Institute,Jingdezhen 333403; 4.Department of Mechanical and Electrical Engineering,Jingdezhen Ceramic Institute,Jingdezhen 333403;
Abstract: Organic semiconductor materials are widely used in thin-film organic devices due to their advantages of low cost and flexible.There is an urgent need to support the development of organic semiconductor materials that have both high mobility and good solubility.However,the functionalization of molecules make it more rigid and solubility is limited.Two kinds of perylene imide derivatives,N,N′-diphenyl perylene tetracarboxylic diimide (DiPP) and N-dodecyl N′-phenyl perylene imide (DoPP) were synthesized to study the effect of long chain alkyl groups on the performance of perylene imide derivatives.The results showed that the introduction of long-chain alkyl greatly improved the solubility of perylene imide derivative,but its thermal stability and oxidation resistance in air decreased.
杨志胜, 柯蔚芳, 王艳香, 黄丽群, 朱华. 非对称苝酰亚胺衍生物的研究[J]. 化工新型材料, 2018, 46(12): 172-174.
Yang Zhisheng, Ke Weifang, Wang Yanxiang, Huang Liqun, Zhu Hua. Study on asymmetric perylene diimide derivative. New Chemical Materials, 2018, 46(12): 172-174.
[1] Bao Z,Rogers J A,Katz H E.Printable organic and polymeric semiconducting materials and devices[J].Journal of Materials Chemistry,1999,9(9):1895-190. [2] Cheng H,Huai J,Cao L,et al.Novel self-assembled phosphonic acids monolayers applied in N-channel perylene diimide (PDI) organic field effect transistors[J].Applied Surface Science,2016,378:545-551. [3] Lu Z H,Jiang B,Zhang X,et al.Perylene-diimide based non-fullerene solar cells with 4.34% efficiency through engineering surface D/A compositions[J].Chemistry of Materials,2014,26(9):2907-2914. [4] Zhang Z G,Qi B,Jin Z,et al.Perylene diimides:a thickness-insensitive cathode interlayer for high performance polymer solar cells[J].Energy & Environmental Science,2014,7(6):1966-1973. [5] Malenfant P R,Dimitrakopoulos C D,Gelorme J D,et al.N-type organic thin-film transistor with high field-effect mobility based on a N,N′-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative[J].Applied Physics Letters,2002,80(14):2517-2519. [6] Tatemichi S,Lchikawa M,Koyama T,et al.High mobility n-type thin-film transistors based on N,N′-ditridecyl perylene diimide with thermal treatments[J].Applied Physics Letters,2006,89(11):112108-112110. [7] Jones B A,Ahrens M J,Yoon M H,et al.High-mobility air-stable n-type semiconductors with processing versatility:dicyanoperylene-3,4:9,10-bis(dicarboximides)[J].Angewandte Chemie International Edition,2004,43(46):6363-6366. [8] Zhao H,Zhang Y Y,Xu H,et al.Synthesis and properties of perylene diimide dyes bearing unsymmetrical and symmetrical phenoxy substituents at bay positions[J].Tetrahedron,2015,71(40):7752-7757. [9] 杨新国.卟啉-苝酰亚胺分子阵列的合成及其电子结构与聚集态结构[D].杭州:浙江大学博士论文,2003. [10] Aguilar-Martinez M,Cuevas G,Jimenez-Estrada M,et al.An experimental and theoretical study of the substituent effects on the redox properties of 2-[(R-phenyl)amine]-1,4-naphthalenediones in acetonitrile[J].The Journal of Organic Chemistry,1999,64(10):3684-3694. [11] Newman C R,Frisbie C D,Ewbank P C,et al.Introduction to organic thin film transistors and design of n-channel organic semiconductors[J].Chemistry of Materials,2004,16(23):4436-4451.