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| 研究生： |
呂玲慧 Ling-Hui Lu |
|---|---|
| 論文名稱： |
四噻吩并蒽為主架構之有機電洞傳輸材料：開發以鈀催化之碳氫鍵活化/芳香環化反應為關鍵步驟之新合成途徑 New Access to Tetrathienoanthracene-Based Hole-Transporting Materials Using Pd-Catalyzed Direct C-H Arylation as Key-Steps |
| 指導教授： |
劉青原
Ching-Yuan Liu |
| 口試委員: | |
| 學位類別： |
碩士 Master |
| 系所名稱： |
工學院 - 化學工程與材料工程學系 Department of Chemical & Materials Engineering |
| 論文出版年： | 2019 |
| 畢業學年度： | 107 |
| 語文別： | 中文 |
| 論文頁數： | 98 |
| 中文關鍵詞： | 四噻吩并蒽 、直接碳氫鍵活化/芳香環化反應 、平面性 |
| 外文關鍵詞： | tetrathienoanthracene (TTA), C-H/C-Br cross-coupling, π-π stacking |
| 相關次數： | 點閱：6 下載：0 |
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廣為人知的spiro-OMeTAD為電洞傳輸材料中的先驅者，具有良好的光電性質，但其合成步驟複雜及製備元件成本高，加上不佳的電洞遷移率，大大限制了它的發展，因此許多學者致力於改善其缺點，並發展出多樣化的有機小分子材料以替代spiro-OMeTAD。
在過去，四噻吩并蒽 (Tetrathienoanthracene, TTA)常應用於有機半導體材料中，已有不錯的發展，而近年將其應用於新興產業的鈣鈦礦太陽能電池中，也得到不錯的光電轉換率，但是在合成四噻吩并蒽衍生物的過程中，多採用高毒性的錫及硼試劑，因此本文捨棄這些對人體及環境有害的金屬試劑，改以鈀金屬催化劑來進行直接碳氫鍵活化/芳香環化反應，此方法改善過去較為繁瑣的合成步驟，接者再以三苯胺衍生物(triphenyl amine, TPA)作為末端基，中間嵌入炔鍵來幫助提升整體的平面性，利用鈀金屬輔以銅金屬催化的Sonogashira反應製備出新型電洞傳輸材料，但由於其具有極高的平面性，雖然可以增加分子間的作用力及堆疊性，並有效提升電荷遷移率，但對有機溶劑會有溶解度不佳的問題，影響元件的光電轉換效率。
本文提供研究者們新的方向，雖然最終結果不盡人意，但卻利用具有步驟經濟與綠色化學的合成方式改良四噻吩并蒽的合成途徑，為合成方法學鋪路。
The perovskite solar cells, the reformative solar cells, become more and more popular. The hole-transporting materials (HTMs) are the most important element influencing on the power conversion efficiency. One of the widely known HTMs was the spiro-OMeTAD, which had great photoelectric properties. But its complicated synthetic procedure, high cost and lower hole mobility inhibited the growth. As the result, the researchers had a study in improving the drawbacks, and developed other small organic molecular materials to substituted for the spiro-OMeTAD. In the past, the tetrathienoanthracene (TTA) became mature in the semiconductors. In the recent years, the TTA used as HTMs applied in the perovskite solar cells, and it had great power conversion efficiencies. However, they synthesized the TTA by the toxic tin reagent and expensive boron reagent. Due to the condition, we dedicated to modifying the synthesis. We synthesized the new TTA-based HTMs by the C-H/C-Br cross-coupling and Sonogashira reaction in perovskite solar cells. It had the alkynyl bond as π-linker, and the triphenylamine derivatives as the donors. Although it had highly planar core conformation enhanced the π-π stacking in film, it had poor solubility resulting in the worst morphology. Thus, the result is disappointing. But it is worth mentioning that it has the less synthetic steps to become more economical by the synthetic methodology I worked.
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