【摘要】：近年來,有機半導體材料以其質(zhì)量輕,品種繁多,成本低廉、環(huán)保等優(yōu)點受到廣泛關(guān)注,根據(jù)電荷傳輸方式不同,有機材料可分為空穴傳輸材料、電子傳輸材料和雙極性傳輸材料,這些材料功能不同可以應用于不同的器件領(lǐng)域,如有機場效應晶體管,有機光伏電池等。多芳烴咪唑類化合物是一類新型有機半導體材料,它具有獨特的π電子離域特性,平面性好,穩(wěn)定性強,遷移率高,能夠?qū)崿F(xiàn)高度有序的分子π-π堆積,在有機電子領(lǐng)域備受關(guān)注,因此,開發(fā)一種新型的多環(huán)芳烴并咪唑有機半導體材料,研究其在有機電子學領(lǐng)域的應用顯得尤為重要�；谝陨涎芯勘尘�,本論文設計并合成了多芳烴咪唑類有機半導體材料,研究了其光學,電化學及熱穩(wěn)定性能。主要包括三方面內(nèi)容:(1)通過Still偶聯(lián)反應,合成了多芳烴咪唑有機半導體材料A~E,咪唑環(huán)中引入烷基鏈調(diào)節(jié)其溶解性,結(jié)構(gòu)中連接噻吩基團,通過硫-硫弱相互作用和π-π相互作用增強分子間作用力,提高器件性能。化合物A~E的分解溫度均大于300度,穩(wěn)定性好,器件制備時不會失活,HOMO能級分別為-5.76 eV,-5.46 eV,-5.80 eV,-5.61 eV,-5.48 eV,說明材料的空氣穩(wěn)定性好,能級和電極材料的功函數(shù)相接近,是合適的場效應晶體管(Organic Field Effect Transistors,OFETs)材料。(2)通過Still偶聯(lián)反應,合成了多芳烴咪唑有機半導體材料F-1,F-2,F-3,G,結(jié)構(gòu)中連接給體并吡咯二酮(DPP),選用D-A-D的分子結(jié)構(gòu)作為太陽能電池的D-A材料,分解溫度大于300度,熱穩(wěn)定性好,HOMO能級分別為-5.69 eV,-5.33 eV,-5.54 eV,-5.41 eV,空氣穩(wěn)定性好,能級和器件的電極材料功函數(shù)相接近,是合適的太陽能電池(Organic Photovoltaics,OPV)材料。(3)設計合成了一個多芳烴咪唑連吡啶有機小分子傳感器H,通過對多種金屬離子的選擇性識別發(fā)現(xiàn)該化合物對Hg2+表現(xiàn)出高選擇性和靈敏度,紫外可見(UV)吸收檢測范圍在5μM~55μM,熒光檢測范圍在1.5μM~10μM。本論文設計的有機功能材料在合成上選用Still偶聯(lián)反應,原理簡單,操作方便,產(chǎn)率相對Suzuki等偶聯(lián)反應高,是偶聯(lián)反應的最佳選擇之一,同時該類材料平面性好,穩(wěn)定性強,遷移率高,能夠?qū)崿F(xiàn)高度有序的分子π-π堆積,在有機電子學領(lǐng)域有很好的發(fā)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.
【學位授予單位】：南京郵電大學
【學位級別】：碩士
【學位授予年份】：2015
【分類號】：TN304.5;O626.23

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