- 學位論文
異丙醇衍生物的合成與半導體性能測試
Synthetic and Semiconductor Performance of Isopropanol derivatives
摘要
與傳統的無機半導體材料相比，有機半導體材料具有加工、成本低、柔性、重量輕和便攜性等優點，因此具有廣闊的應用前景。目前，基於芳香胺類化合物的有機半導體材料已經被廣泛研究和應用於有機光電子領域。在這些芳香胺類有機半導體材料中，異丙醇類衍生物引起了人們廣泛的關注。異丙醇類衍生物大的平面剛性結構使得這類化合物具有良好的熱穩定性。此外，異丙醇類衍生物具有一個非常顯著的優點，就是它能夠非常容易進行功能化，即可以通過化學修飾的方法在異丙醇類衍生物上引入一些功能性的基團，從而得到一系列新的有機半導體材料。在本文中，我們以異丙醇爲母體，設計、合成了一系列新的有機半導體材料，研究了這些材料的熱學、光學、電學等物理化學性質，通過對化合物晶體結構的分析闡述了分子結構與載流子傳輸性能之間的關系，並制作了有機電致發光元件和有機薄膜場效應元件來表征這些材料的載流子傳輸性能。論文的主要內容如下： (1)得到了7個異丙醇衍生物的單晶，並採用質譜法和核磁共振方法測定了它們的晶體結構，並對它們的分子結構和排列堆積特點進行了詳細的分析。異丙醇類衍生物的晶體結構數據表明:異丙醇類衍生物具有優良的平面性，端基的取代基與異丙醇之間都存在不同程度的扭轉角。在異丙醇類化合物的晶體中，分子存在兩種排列堆積方式:Herringhone型堆積和: π-π堆積。這兩種排列堆積方式都有利於載流子的傳輸，這說明異丙醇類衍生物可以成爲壹類優良的有機半導體材料。 (2)以異丙醇衍生物作爲空穴傳輸層， Alq3作爲電子傳輸層和發光層制作了有機電致發光元件。所有的元件都發出綠光，說明載流子的複合區域在Alq3。這表明異丙醇衍生物可以作爲空穴傳輸材料，具有良好的空穴傳輸性能。 研究了異丙醇衍生物生産中産生的異丙醇-環氧氯丙烷廢液的回收利用方法。先以水爲萃取劑,對異丙醇-環氧氯丙烷混合物進行萃取分離,得到粗環己烷和異丙醇水溶液,粗環己烷經精餾提純,得到純度爲99. 80%環氧氯丙烷産品;異丙醇水溶液經恒沸精餾得純度爲99. 55%異丙醇。
並列摘要
Organic semiconductors offer potential advantages over conventional inorganic semiconduxtor due to their easy processing, lower cost, and flexibility. Organic semiconductors based on arylamine have been extensively studied and applied as hole-transporting materials for optoelectronic applications. Among arylamine semiconductors, Isopropanol derivatives are an appealing system for studies because it has a relatively large and planar molecular structure to enable facile establishment of higher structural order for charge transport, and is therefore expected to be environmentally far more stable. The main contribution of this thesis is exploring the new organic semiconductors based on isopropanol derivatives. Crystal structures of the Isopropanol derivatives semiconductors were determined and studied carefully. The electrical, optical and other properties and potential applications of these materials and devices in organic electronics were discussed in detail. The primary results are as follows: (1) Seven single crystals of isopropanol derivatives organic semiconductors were obtained and their crystal structures were determined by mass and NMR analyses to study the substituent effect on molecular conformation, packing characteristics, and the conrelations between the crystal structure and the electrical characteristics. NMR structure analysis of the single crystals reveals that the inner isopropanol derivatives plane displays a quasi-planar structure with very small dihedral angles between each rings of isopropanol derivatives. There exists two kinds of packing patterns in the packing diagrams of isopropanol derivatives: herringbone packing and π-π packing. This packing character will facilitate charge transport. (2) Organic light-emitting diodes (OLEDs) using isopropanol-based organic semiconductors as hole-transporting materials were fabricated. Alq3 was used as electron-transporting and emitting layer. All the devices emitted green light. The devices using the triphenylamine-substituted or fluorene-substituted isopropanol derivatives as hole-transporting materials showed good EL performance, while that using carbazole-substituted derivatives showed poor El performance. This results indicated that isopropanol-based organic semiconductors can be served excellent hole-transporting materials for OLEDs and the substituents have great effects on the hole-transporting performance of isopropanol -based hole-transporting materials. A physical extraction and distillation method was applied to the separation of an isopropanol-cyclohexanemixture to obtain pure cyclohexane and pure isopropanol liquids. Firstly, with water as an extraction agen,t an extraction process would be carried out in the isopropanol-cyclohexane mixture to obtain raw cyclohexane liquid and isopropanolliquid. Through general distillation for purities, a 99.80% cyclohexane liquid was obtained. And through azeotropic distillation, a 99.55% isopropanol coboiling substance liquid was obtained.