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研究生: 張恩銓
Chang, En-Chiuan
論文名稱: 合成含有1,3,4-口咢二唑環及咔唑環之吡唑類衍生物及其在有機電致激發光元件之應用
Synthesis of the Pyrazole Derivatives Containing Carbazole and 1,3,4-Oxadiazole Rings and Applied to Organic Electro-Luminescence Devices
指導教授: 葉茂榮
Yeh, Mou-Yung
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2007
畢業學年度: 95
語文別: 中文
論文頁數: 100
中文關鍵詞: 1,3,4-口咢二唑環有機發光二極體雪梨酮
外文關鍵詞: 1,3,4-Oxadiazole, parazole, OLED
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  • 本論文主要以研究吡唑類之衍生物於光電材料上之應用。而吡唑類衍生物之合成係以雪梨酮為起始物進行1,3雙偶極環化加成反應而得到含吡唑環之化合物,進一步合成各類吡唑類衍生物,再將之應用於發光材料之領域。
    本論文為研究小分子有機發光二極體之材料,材料之合成以雪梨酮為起始物進行衍生,合成出含有吡唑環與1,3,4-口咢二唑環之化合物,再進一步衍生出含有不同官能基之有機發光二極體材料。利用此類之設計合成出多種光電材料,並對其物理性質、化學性質、光電性質做深入之探討。
    近來之期刊報導常見吡唑環與口咢二唑環之化合物被應用於光電材料上,因此,本研究除了採用上述兩種雜環官能基當做分子骨架,另外導入咔唑類之具有高熱穩定性之官能基,以提升分子結構之剛性,而高熱穩定性分子之小分子發光材料其優點在於真空熱蒸鍍時不易發生燒結之現象,且組成元件後之使用壽命也會有相對之提升。

    In this study, I had synthesized a series of pyrazole derivatives, and applied in organic electro-luminescence devices. The series of pyrazole derivatives were all synthesized from sydnone via 1,3-dipolar cycloaddition.
    Organic light-emitting diode (OLED) is a novel technology. The large size display can be made via this technology. Because of some organic materials have high fluorescence efficiency and semiconducting properties, they often applicable to
    electro-luminescence (EL) devices. The other hand, the emission colors can be determine via modify organic compounds. Hence, the organic material plays a decisive role in OLED technology.
    Compounds derived from 1,3,4-oxadiazoles had been reported having good electron-transporting properties and the pyrazole moiety is an electron-rich heterocycle. So we introduced 1,3,4-oxadiazoles into pyrazole derivatives. In order to improve thermostabilities and electro-luminescence properties, we introduced carcazole and phenyl into 1,3,4-oxadiazole-based pyrazole derivatives.
    The physical 、 chemical and electro-luminescence properties were studied by DSC 、 UV-Vis 、 CV and PL spectra. The OLED device was constructed by vapor deposition of the materials under vacuum onto the ITO-coated glass substrate. The I-V curves and EL spectra had proven that our new synthetic compounds were new efficient blue electroluminescent materials.

    目錄……………………………………………………………………….. 表目錄……………………………………………………………………... 圖目錄……………………………………………………………………... 英文摘要…………………………………………………………………. 中文摘要…………………………………………………………………. 第一章 雪梨酮化合物之簡介………………….……………………….1 1-1 前言……………………………………………………………1 1-2 雪梨酮化合物之合成…………………………………………4 1-3 雪梨酮的反應性………………………………………………6 1-4 雪梨酮化合物的藥理活性…………………………………..15 第二章 有機發光二極體簡介…………………………………………16 2-1 前言…………………………………………………………..16 2-2 有機發光二極體的元件架構及發光原理…………………..18 2-3 小分子與高分子發光材料之比較…………………………...25 2-4 發光原理……………………………………………………...26 2-5 真空熱蒸鍍……………………………………………………27 第三章 含口咢二唑環之有機發光材料的合成…………………………..30 3-1 合成具有口咢二唑官能基之雜環化合物………………………33 3-2 合成具有咔唑官能基之雜環化合物…………………………42 3-3 實驗部份………………………………………………………49 3-4 實驗藥品………………………………………………………71 第四章 光電性質測試………………………………………………….73 4-1 前言……………………………………………………………73 4-2 測試儀器………………………………………………………74 4-3 紫外光-可見光吸收光譜……………………………………..75 4-4 螢光放射光譜…………………………………………………81 4-5 循環伏安法……………………………………………………85 第五章 元件組裝………………………………………………………..92 5-1 前言…………………………………………………………....92 5-2 發光二極體的電流-電壓分析………………………………..94 5-3 電致光測試…………………………………………………….95 第六章 結論……………………………………………………...………96 參考文獻………………………………………………………………….98

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