新型D-A结构有机光电材料的合成及性能研究

发布时间：2018-07-23 11:54

【摘要】：在目前报道的有机光电材料中,给体-受体(Donor-Acceptor)二元体系的构建所展现出来的优良的光电性能日益得到人们广泛的关注。D-A分子体系在有机光电材料中有许多优势,能够同时进行空穴和电子分离迁移;给体和受体之间能够发生光诱导电子转移和能量转移,且能够通过调控给体或受体部分的分子结构和性质以及连接方式来有效地调节光谱和能级;在氯仿等常规有机溶剂的溶解性较好等,以其为理念设计的有机光电材料,具有很好地发展应用前景。其中,三芳胺作为电子给体,具备高的摩尔消光系数,优异的空穴迁移性能和强的给电子能力,其衍生物近年来受到广泛关注。本文设计合成了一系列以三苯胺、咔唑和吲哚啉等芳胺衍生物作为电子给体,均三嗪环作为电子受体的D-A型光诱导电荷转移体系,系统研究了其光电性质。首先,利用Ullmann反应完成了C-N键的耦合,得到了芳胺类母体化合物,之后,利用Vilsmeier反应和Wittig反应引入苯乙烯基骨架,得到端位硝基取代的染料分子中间体3a、3b、3c、3d、3e和3f。之后,通过对硝基进行还原反应得到氨基,并进一步进行亲核取代反应引入了均三嗪环,得到了染料分子5a、5b、5c、5d、5e和5f,与此同时,通过1H NMR,13C NMR和HRMS等对获得的染料分子及其中间体进行了表征,确定了化合物结构。通过紫外-可见吸收光谱、稳态荧光发射光谱和循环伏安对目标化合物及其硝基中间体的光物理及电化学性质进行了研究。二者结果表明,具有平面刚性构型的9-苯基咔唑基团化合物相比于含螺旋桨构型三苯胺基团化合物,表现出较弱的ICT作用;同时在三苯胺基团上引入给电子官能团则有利于增强化合物的ICT作用;此外,含吲哚啉基团化合物则证明比三苯胺基团化合物表现出更强的ICT作用。
[Abstract]:Among the reported organic optoelectronic materials, the excellent optoelectronic properties of the donor-receptor (Donor-Acceptor) binary system have attracted more and more attention. The D-A molecular system has many advantages in the organic optoelectronic materials. The photo-induced electron transfer and energy transfer can occur between the donor and the acceptor. And it can regulate the spectrum and energy level effectively by regulating the molecular structure and properties of donor or receptor parts, and the organic optoelectronic materials designed with the idea of chloroform, such as good solubility of conventional organic solvents, etc. It has a good prospect of development and application. Among them, triarylamine, as an electron donor, has high molar extinction coefficient, excellent hole migration performance and strong electron delivery ability, and its derivatives have attracted wide attention in recent years. In this paper, a series of D-A photoinduced charge transfer systems with trianiline, carbazole and indoline derivatives as electron donors and triazine ring as electron receptors have been designed and synthesized, and their photoelectric properties have been systematically studied. First, the C-N bond was coupled by Ullmann reaction, and the aromatic amines were obtained. Then the styrene matrix was introduced by Vilsmeier reaction and Wittig reaction. After that, the amino group was obtained by the reduction reaction of nitrogen-4, and then the nucleophilic substitution reaction was carried out. The ring of m-triazine was introduced, and the dye molecules of 5aah5bn5ccn5dn5e and 5f. were obtained, at the same time, The obtained dye molecules and their intermediates were characterized by 1H-NMR-13C NMR and HRMS, and the structure of the compounds was determined. The photophysical and electrochemical properties of the target compounds and their nitro intermediates were studied by UV-Vis absorption spectra, steady-state fluorescence emission spectra and cyclic voltammetry. The results show that the 9- phenyl carbazole group compounds with plane rigid configuration have weaker ICT effect than those with propeller configuration trianiline group compounds. At the same time, the addition of electron functional groups to the trianiline group was beneficial to the enhancement of the ICT effect of the compounds, and the ICT effect of the compounds containing indoline groups was stronger than that of the trianiline group compounds.
【学位授予单位】：天津大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TB34

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