c-HBC衍生物及其低聚物的合成与表征

发布时间：2018-04-28 00:25

本文选题：有机太阳能电池 + 有机光电材料　；参考：《上海师范大学》2017年硕士论文

【摘要】：有机光电材料以其易加工、光电响应快、存储密度高等优点被广泛应用于发光二极管、有机晶体管、有机太阳能电池、有机存储器等有机电子领域。这些应用领域之间可以说既有共性又有差异;共性是都是利用这些材料的半导体的光电性质来达到相应的性能,而差异则体现在不同的功能要求有不同的化学结构来实现。由此可见,有机光电材料的性能和结构之间有着密切的关系。对它们的深入研究有助于为设计和优化出新型的材料、探索新颖的器件和广泛的应用起到指导性的作用。稠环芳烃作为有机光电材料中的明星材料,主要是由于其在光电子器件中表现出优异的性能。稠环芳烃根据形态可分为平面型与非平面型两种;与平面型稠环芳烃相比,首先,扭曲的结构使得材料的内在物理特性发生了很大的改变;其次,这种非平面的性质导致其在晶体薄膜以及多晶薄膜中分子之间的接触呈现出多样化,进而提升了以有机材料为基础的器件的电荷传输性能;此外,这类芳烃的非平面结构可以为富勒烯等具有凸形结构的物质产生很好的吻合,为富勒烯的分离提纯提供了途径,而且在有机光伏器件中通过有序的p-n结提高了其的自组装性能;最后,这些材料在有机溶剂中具有较好的溶解性并且在溶剂中进行自发聚合的可能性也不大,所以可以通过溶液处理的方法来制备此类材料。本论文主要是基于非平面的六苯并蔻(c-HBC)进行了一系列的研究工作,从以下三个大的方面进行论述:(一)我们设计并合成出了三种具有取代基的c-HBC例如含有十二烷氧基、溴取代基以及三甲基硅取代基。在HBC分子中引入十二烷氧基主要是为了提高其在常规有机溶剂中的溶解性;引入溴取代基主要是由于溴原子既是一个易离去基团又是一个反应活性点可以进行各种偶联反应;而引入三甲基硅这样一个取代基主要是由于其的易离去性,可以在四取代HBC上进行预期的反应得到想要的材料。(二)通过在溴取代的HBC上进行上丙炔基反应,得到含有丙炔基取代的HBC;然后进行炔烃复分解反应将单个的HBC分子通过碳碳三键连接起来,形成一个大的派电子离域体系。(三)四溴取代的HBC分子通过Yamamoto偶联反应生成纳米球状的低聚物,对该材料的热稳定性、光吸收性质以及空间构型进行了一系列的研究。
[Abstract]:Organic optoelectronic materials are widely used in the fields of light emitting diodes, organic transistors, organic solar cells, organic memory and other organic electronics due to their advantages of easy processing, fast photoelectric response and high storage density. These applications can be said to have both generality and difference. The commonality is to use the photoelectric properties of the semiconductors of these materials to achieve the corresponding performance, and the difference is reflected in the different functional requirements of different chemical structures to achieve. It can be seen that there is a close relationship between the properties and structure of organic optoelectronic materials. Their in-depth study is helpful for the design and optimization of new materials, the exploration of novel devices and wide applications. As a star material in organic optoelectronic materials, polycyclic aromatic hydrocarbons (PAHs) are mainly due to their excellent performance in optoelectronic devices. Polycyclic aromatic hydrocarbons can be divided into plane type and non-plane type according to their morphology. Firstly, the distorted structure changes the physical properties of the material greatly. This nonplanar property leads to a variety of contacts between molecules in both crystalline and polycrystalline films, which in turn improves the charge transport performance of organic material-based devices. The nonplanar structure of this kind of aromatics can produce a good agreement for fullerenes and other substances with convex structure, which provides a way for the separation and purification of fullerenes, and improves their self-assembly performance in organic photovoltaic devices through ordered p-n junctions. Finally, these materials have good solubility in organic solvents and the possibility of spontaneous polymerization in solvents is not great, so they can be prepared by solution treatment. In this paper, a series of research work is conducted based on the nonplanar hexabenzocorbium c-HBC. We discuss the following three aspects: (1) We have designed and synthesized three kinds of c-HBC with substituents, such as dodecoxy groups. Bromine substituents and trimethyl silicon substituents. The main purpose of introducing dodecoxy into HBC is to improve its solubility in conventional organic solvents, and the bromine substituent is mainly due to the fact that the bromine atom is both an easily departed group and a reactive active point for various coupling reactions. The introduction of trimethyl silicon as a substituent is mainly due to its easy to leave, so the desired material can be obtained by the expected reaction on tetrasubstituted HBC. (2) HBCs containing propargyl substituents were obtained by the reaction of propargyl groups on brominated HBC, and then the individual HBC molecules were connected by carbon-carbon triple bonds to form a large para-electron delocalization system. (3) the tetrabromo-substituted HBC molecules were synthesized into spherical oligomers by Yamamoto coupling reaction. The thermal stability, optical absorption properties and spatial configuration of the materials were studied.
【学位授予单位】：上海师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：TB34;O625

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