多芳基取代环戊二烯衍生物的合成及其光电性质的研究

发布时间：2018-02-16 21:38

  本文关键词： 有机电致发光 环戊二烯衍生物 聚集诱导发光增强 分子内电荷转移化合物 有机微纳米材料 晶体结构　出处：《大连理工大学》2015年硕士论文　论文类型：学位论文

【摘要】：有机发光二极管因其结构简单、视角宽、能耗低、亮度高等优点在平板显示领域展现了广阔应用前景,吸引了学术界和工业界的极大兴趣。5见有的蓝光材料的发光效率、寿命和成膜性等尚不如人意,制约了全色显示的有机发光器件的发展。本论文通过改变取代基结构来调控分子能级和发光性质,设计合成了系列具有聚集诱导发光增强(AIEE)和分子内电荷转移(ICT)性质的蓝光多芳基取代环戊二稀衍生物,对其结构、光致发光性质、电化学性质和有机电致发光性质进行了研究,通过晶体结构、紫外吸收光谱、焚光光谱和量子化学计算研究了其发光机理;并对部分化合物的纳米聚集体组装行为和发光性质进行了研究。论文主要研究内容包括以下部分:1.具有AIEE性质的多芳基取代环戊二烯衍生物的合成与性质研究。引入噻盼基团和二苯并噻盼基团设计合成了三种蓝色焚光多芳基取代环戊二稀衍生物DPCP 1-3,通过iHNMR、i3CNMR、HRMS和X-射线单晶衍射表征了化合物的结构;研究了其热稳定性质、光物理性质、电化学性质;紫外和突光光谱研究表明化合物DPCP 1和DPCP3具有AIEE性质;利用X-射线单晶结构分析、光谱分析和量子化学计算研究了AIEE性质机理;以化合物DPCP 3为发光层制备了简单的蓝光器件,开启电压为3.2V,最大亮度为2277cd/m2,电流效率为0.42cd/A。2.具有ICT性质的多芳基取代环戊二稀衍生物的合成与性质研究。引入三苯胺基团、蒽和芘环设计合成了三种多芳基取代环戊二稀衍生物0?〔?4-6,通过1只\1411、NMR、HRMS和X-射线单晶衍射对化合物结构进行了表征;紫外光谱和荧光光谱研究表明化合物具有分子内电荷转移性质;在二氯甲烧溶液中的的荧光量子效率相对于引入的单体基团而言提高了近1倍;化合物展现了良好的热稳定性;分别以DPCP 5和DPCP 6为发光层制备了简单的三层器件结构,器件显示了良好的电致发光性能,开启电压分别为3.6V和3.5V,最大亮度分别为1195 cd/m2和2895 cd/m2,电流效率分别为1.2 cd/A和1.1 cd/A。3.多芳基取代环戊二稀衍生物的微纳米结构调控和发光性质研究。分别懫用了溶剂挥发法和再沉淀法制备了三种化合物微纳米颗粒,研究了溶剂对其聚集态结构形貌的可控影响。通过组装条件的改变,纳米晶粒形貌从球形向棒形转变。通过晶体的堆积模式和纳米颗粒生长过程推测了其生长机理,并通过突光光谱测试、突光寿命测试研究了颗粒形貌与发光性质之间的联系。
[Abstract]:Because of its simple structure, wide viewing angle, low energy consumption and high brightness, organic light-emitting diodes (OLEDs) have shown a broad application prospect in flat panel display, and attracted great interest from academia and industry. The development of panchromatic organic luminescent devices is restricted by the unsatisfying lifetime and film-forming properties. In this paper, the molecular energy levels and luminescence properties are regulated by changing the substituent structure. A series of blue light polyaryl substituted cyclopentadiene derivatives with aggregation induced luminescence enhancement (AIEE) and intramolecular charge transfer (ICTI) were designed and synthesized. Their structures, photoluminescence properties, electrochemical properties and organic electroluminescence properties were studied. The luminescence mechanism was studied by crystal structure, UV absorption spectrum, immolation spectrum and quantum chemistry. The synthesis and properties of polyaryl substituted cyclopentadiene derivatives with AIEE properties were studied. Three blue light-immolated polyaryl substituted cyclopentadiene derivatives DPCP 1-3 were designed and synthesized by introducing thiopan group and dibenzo-thiopan group. The structures of the compounds were characterized by iHNMR-i3CNMR-HRMS and X-ray single crystal diffraction. The thermal stability, photophysical properties and electrochemical properties of the compounds were studied. UV and light bursting spectra showed that the compounds DPCP 1 and DPCP3 had AIEE properties. Spectroscopic analysis and quantum chemical calculation were used to study the mechanism of AIEE properties. A simple blue light device was prepared by using compound DPCP _ 3 as the luminescent layer. The opening voltage is 3.2V, the maximum brightness is 2277cd / m2, and the current efficiency is 0.42cd / A.2.The synthesis and properties of polyaryl substituted cyclopentadiene derivatives with ICT properties are studied. Three polyarylsubstituted cyclopentadiene derivatives have been designed and synthesized by introducing trianiline groups, anthracene and pyrene rings. What? 4-6, the structure of the compound was characterized by single crystal X-ray diffraction and HRMS, UV and fluorescence spectra showed that the compounds had intramolecular charge transfer properties. The fluorescence quantum efficiency in dichloromethylene-fired solution was nearly doubled compared with the monomer group introduced, the compounds exhibited good thermal stability, and simple three-layer device structures were fabricated using DPCP _ 5 and DPCP _ 6 as luminescent layers, respectively. The device shows good electroluminescence performance. The threshold voltage is 3.6V and 3.5V, the maximum brightness is 1195 cd/m2 and 2895 CD / m ~ 2, and the current efficiency is 1.2 cd/A and 1.1 CD / A. 3.The structure regulation and luminescence properties of polyaryl substituted cyclopentadiene derivatives are studied. Three kinds of compound microparticles were prepared by hair method and reprecipitation method. The controllable effect of solvent on the morphology of the aggregation state was studied. The morphology of nanocrystalline changed from sphere to bar by changing the assembly conditions. The growth mechanism was deduced by the stacking mode of crystal and the growth process of nanoparticles. The relationship between particle morphology and luminescent properties was studied by means of luminous spectrum and lifetime measurement.
【学位授予单位】：大连理工大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TN383.1;TQ231.22
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本文编号：1516488