多芳烃并咪唑类有机半导体材料的设计、合成及性质研究
发布时间：2018-08-11 12:45
【摘要】：近年来,有机半导体材料以其质量轻,品种繁多,成本低廉、环保等优点受到广泛关注,根据电荷传输方式不同,有机材料可分为空穴传输材料、电子传输材料和双极性传输材料,这些材料功能不同可以应用于不同的器件领域,如有机场效应晶体管,有机光伏电池等。多芳烃咪唑类化合物是一类新型有机半导体材料,它具有独特的π电子离域特性,平面性好,稳定性强,迁移率高,能够实现高度有序的分子π-π堆积,在有机电子领域备受关注,因此,开发一种新型的多环芳烃并咪唑有机半导体材料,研究其在有机电子学领域的应用显得尤为重要。基于以上研究背景,本论文设计并合成了多芳烃咪唑类有机半导体材料,研究了其光学,电化学及热稳定性能。主要包括三方面内容:(1)通过Still偶联反应,合成了多芳烃咪唑有机半导体材料A~E,咪唑环中引入烷基链调节其溶解性,结构中连接噻吩基团,通过硫-硫弱相互作用和π-π相互作用增强分子间作用力,提高器件性能。化合物A~E的分解温度均大于300度,稳定性好,器件制备时不会失活,HOMO能级分别为-5.76 eV,-5.46 eV,-5.80 eV,-5.61 eV,-5.48 eV,说明材料的空气稳定性好,能级和电极材料的功函数相接近,是合适的场效应晶体管(Organic Field Effect Transistors,OFETs)材料。(2)通过Still偶联反应,合成了多芳烃咪唑有机半导体材料F-1,F-2,F-3,G,结构中连接给体并吡咯二酮(DPP),选用D-A-D的分子结构作为太阳能电池的D-A材料,分解温度大于300度,热稳定性好,HOMO能级分别为-5.69 eV,-5.33 eV,-5.54 eV,-5.41 eV,空气稳定性好,能级和器件的电极材料功函数相接近,是合适的太阳能电池(Organic Photovoltaics,OPV)材料。(3)设计合成了一个多芳烃咪唑连吡啶有机小分子传感器H,通过对多种金属离子的选择性识别发现该化合物对Hg2+表现出高选择性和灵敏度,紫外可见(UV)吸收检测范围在5μM~55μM,荧光检测范围在1.5μM~10μM。本论文设计的有机功能材料在合成上选用Still偶联反应,原理简单,操作方便,产率相对Suzuki等偶联反应高,是偶联反应的最佳选择之一,同时该类材料平面性好,稳定性强,迁移率高,能够实现高度有序的分子π-π堆积,在有机电子学领域有很好的发展前景。
[Abstract]:In recent years, organic semiconductor materials have attracted wide attention due to their advantages of light weight, variety, low cost, environmental protection, etc. According to different charge transfer modes, organic materials can be divided into hole-transport materials. Electronic transport materials and bipolar transport materials can be used in different devices such as airfield effect transistors organic photovoltaic cells and so on. Polyaromatics imidazole compounds are a new kind of organic semiconductor materials, which have unique 蟺 electron delocalization properties, good planarity, strong stability, high mobility, and can achieve highly ordered 蟺-蟺 stacking. In the field of organic electronics, it is very important to develop a novel polycyclic aromatic hydrocarbons (PAHs) and imidazole organic semiconductors and to study their applications in the field of organic electronics. Based on the above research background, the optical, electrochemical and thermal stability of polyaromatics imidazole organic semiconductors were designed and synthesized. The main contents are as follows: (1) polyaromatic imidazole organic semiconductors were synthesized by Still coupling reaction. The alkyl chain was introduced into the imidazole ring to regulate its solubility and the thiophene group was connected to the structure. The intermolecular force is enhanced by the weak sulfur-sulfur interaction and 蟺-蟺 interaction, and the device performance is improved. The decomposition temperature of compound Agne is more than 300 degrees, and its stability is good. The Homo energy levels are -5.76 EV ~ (-1) -5.46 EV ~ (-1) -5.80 EV ~ (-1) -5.61 EV ~ (-1) -5.48 EV, respectively, indicating that the air stability of the material is good, and the energy level is close to the work function of the electrode material. It is a suitable material of (Organic Field Effect transistors (Organic Field Effect transistorsOFETs). (2) A polyaromatic imidazole organic semiconductor material, F-1F2F3OFETs, was synthesized by Still coupling reaction, in which the donor and pyrrolidone (DPP), were used as D-A materials for solar cells. The decomposition temperature is more than 300 degrees, and the Homo level is -5.69 EV ~ 5.33 EV ~ 5.33 EV ~ 5.54 EV ~ 5.54 EV ~ 5.41 EV, respectively. The energy level is close to the work function of the electrode material. It is a suitable material for Organic photovoltaic cells. (3) A polyaromatic imidazole and pyridine organic small molecule sensor H has been designed and synthesized. It is found that the compound has high selectivity and sensitivity to Hg2 by selective recognition of various metal ions. The detection range of UV-Vis (UV) was 55 渭 M and the fluorescence detection range was 1.5 渭 M ~ 10 渭 M. In this paper, Still coupling reaction is used in the synthesis of organic functional materials. The principle is simple, the operation is convenient, the yield is higher than that of Suzuki and so on, so it is one of the best choice for the coupling reaction. At the same time, this kind of material has good planarity and stability. Because of its high mobility and highly ordered molecular 蟺-蟺 stacking, it has a good prospect in the field of organic electronics.
【学位授予单位】：南京邮电大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TN304.5;O626.23
[Abstract]:In recent years, organic semiconductor materials have attracted wide attention due to their advantages of light weight, variety, low cost, environmental protection, etc. According to different charge transfer modes, organic materials can be divided into hole-transport materials. Electronic transport materials and bipolar transport materials can be used in different devices such as airfield effect transistors organic photovoltaic cells and so on. Polyaromatics imidazole compounds are a new kind of organic semiconductor materials, which have unique 蟺 electron delocalization properties, good planarity, strong stability, high mobility, and can achieve highly ordered 蟺-蟺 stacking. In the field of organic electronics, it is very important to develop a novel polycyclic aromatic hydrocarbons (PAHs) and imidazole organic semiconductors and to study their applications in the field of organic electronics. Based on the above research background, the optical, electrochemical and thermal stability of polyaromatics imidazole organic semiconductors were designed and synthesized. The main contents are as follows: (1) polyaromatic imidazole organic semiconductors were synthesized by Still coupling reaction. The alkyl chain was introduced into the imidazole ring to regulate its solubility and the thiophene group was connected to the structure. The intermolecular force is enhanced by the weak sulfur-sulfur interaction and 蟺-蟺 interaction, and the device performance is improved. The decomposition temperature of compound Agne is more than 300 degrees, and its stability is good. The Homo energy levels are -5.76 EV ~ (-1) -5.46 EV ~ (-1) -5.80 EV ~ (-1) -5.61 EV ~ (-1) -5.48 EV, respectively, indicating that the air stability of the material is good, and the energy level is close to the work function of the electrode material. It is a suitable material of (Organic Field Effect transistors (Organic Field Effect transistorsOFETs). (2) A polyaromatic imidazole organic semiconductor material, F-1F2F3OFETs, was synthesized by Still coupling reaction, in which the donor and pyrrolidone (DPP), were used as D-A materials for solar cells. The decomposition temperature is more than 300 degrees, and the Homo level is -5.69 EV ~ 5.33 EV ~ 5.33 EV ~ 5.54 EV ~ 5.54 EV ~ 5.41 EV, respectively. The energy level is close to the work function of the electrode material. It is a suitable material for Organic photovoltaic cells. (3) A polyaromatic imidazole and pyridine organic small molecule sensor H has been designed and synthesized. It is found that the compound has high selectivity and sensitivity to Hg2 by selective recognition of various metal ions. The detection range of UV-Vis (UV) was 55 渭 M and the fluorescence detection range was 1.5 渭 M ~ 10 渭 M. In this paper, Still coupling reaction is used in the synthesis of organic functional materials. The principle is simple, the operation is convenient, the yield is higher than that of Suzuki and so on, so it is one of the best choice for the coupling reaction. At the same time, this kind of material has good planarity and stability. Because of its high mobility and highly ordered molecular 蟺-蟺 stacking, it has a good prospect in the field of organic electronics.
【学位授予单位】：南京邮电大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TN304.5;O626.23
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