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研究生: 黃玉廷
Huang, Yu-Ting
論文名稱: 苯環-異喹碄金屬與1-吡啶-萘環銥金屬錯合物於有機發光元件的應用
Application of Phenyl-Isoquinoline And Naphthalen-1-yl-Pyridine Iridium Complexes In The Organic Light Emitting Diodes
指導教授: 孫亦文
Sun, I-Wen
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: 2006
畢業學年度: 94
語文別: 中文
論文頁數: 115
中文關鍵詞: 有機發光元件銥金屬錯合物
外文關鍵詞: Iridium Complexes, Organic Light-Emitting Diodes
相關次數: 點閱:101下載:1
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  • 本論文的目的在於研究合成兩大系列的銥錯合物:一,苯基-異喹琳銥金屬乙醯丙酮。二,吡碇-萘環銥金屬-乙醯丙酮錯合物。且了解其在有機電激發光體材料上的應用。延伸本實驗室之前的紅光材料結構,第一個工作,我們首先在苯基-異喹碄配位基上,將單取代換成雙取代的甲基或甲氧基,去觀察其在合成上及光電性質的變化。而第二個工作,我們將主體換成1-吡啶-萘環配位基,在吡啶環上做不同位置的甲基或甲氧基取代。我們將此些材料當作OLED的摻雜物,分別放出紅光與黃橘光。其中,具有立體障礙的結構通常在合成上遭遇困難,而有趣的是;6a1雖預期有立體障礙,卻可成功的被合成,且順利得到單晶;從X-ray數據證明在異喹碄上C-3上確具有較大的立體障礙。另外第二系列的(6-monp)2Ir(acac)成功地由雙體的單晶證明了其立體障礙的存在。在電化學方面顯示,此二系列銥錯合物各自具有相似的能障,但其在氧化半電位的表現則有明顯的不同,說明了取代基位置的改變仍會影響氧化性質。在第一系列的元件性質中,其CIE為(x=0.67,y=0.33),而在高電流密度63.69mA/cm2下,展現最佳亮度9299.36 cd/m2;在0.28 mA/cm2下得到最好的發光效率21.96 cd/A,證明了這些錯合物具有被應用於有機發光二極體發光材料的可能性。

    We studies the synthesis and photophysical properties of a series of bi-substituted
    Phenyl-isoquinoline iridium (III) complexes and Naphthalen-1-yl-pyridine iridium complexes. Extending the research of red phosphorescent materials in our lab,the first work focus on the bi-substituted effect in the phenyl-isoquinoline iridium complexes. The second work focus on changing the substituted situation of the methyl or methoxy group on the pyridine ring. And we also report the synthesis and OLED devices of red electrophosphorescent dopant materials. In synthesis, usually it’s hard to smoothly synthesis the complex which have the steric hindrance. Interestingly, the bis[3-methyl-1-p-toly lisoquinolinato-N,C2’] iridium (III) (acetylacetonate)(6a1) could be prepared even though the single crystal X-ray crystallography data showed that there was a steric hindrance due to the methyl group on the C-3 position to isoquinoli -ne. On the other hand, the complex (6-monp)2Ir(acac) of the second work couldn’t be prepared and also we can get the X-ray crystallography data of the dimmer single crystal showed that there was a steric hindrance due to the methoxy group on the C-6 position to pyridine. Noticeably, the cyclic voltammetric (CV) measurements indicated that although these iridium (III) complexes have similar energy gaps, their E1/2(ox) are different. These illustrate that the major influence of oxidation potential for iridium (III) complexes is the substituted isoquinoline ring and the pyridine ring. While all these complexes in the first series emitted in the red region, the bis[5-Methyl-1-p-tolylisoquinolinato-N,C2’] iridium (III) (acetylacetonate) (6c1) showed a higher brightness of 9299.36 cd/m2 at a higher current density of J = 63.69 mA/cm2 and a better luminance efficiency of 21.96 cd/A at a current density of J = 0.28 mA/cm2. The corresponding CIE coordinate is x = 0.67, y = 0.33. This proves that iridium (III) complexes are excellent dopants for OLEDs.

    目錄.................................................... IV 表目錄..................................................VII 圖目錄................................................ VIII 名詞縮寫..................................................X 第一章 緒論 1-1 前言...............................................1 1-2 有機材料在發光二極體的發展.........................4 1-3 有激電激發光元件結構...............................5 1-4 吸收與放射-螢光與磷光..............................9 1-5 主體發光材料與摻雜發光材料........................13 1-6 磷光紅光摻雜材料在有機二極體(OLED)的發展........17 第二章 實驗部份.........................................21 2-1 使用藥品..........................................21 2-2 實驗相關儀器操作..................................22 2-3 苯環-異喹碄系列銥金屬錯合物.......................24 2-3-1 合成..............................................24 2-4 萘環-吡啶系列銥金屬錯合物.........................31 2-4-1 配位基的合成......................................31 2-4-2 銥金屬錯合物的合成................................34 第三章 結果與討論........................................37 3-1 第一系列-苯環-異喹琳系列銥金屬錯合物.............37 3-1-1 合成..............................................37 3-1-2 X光單晶繞射.......................................38 3-1-3 UV-Vis吸收光譜....................................45 3-1-4 Photoluminescence (PL) 放光光譜.................47 3-1-5 量子產率的測量....................................49 3-1-6 循環伏安法........................................51 3-1-7 OLEDs的製備.......................................59 3-2 第二系列1-吡啶-萘環系列銥金屬錯合物合成............67 3-2-1 合成 3-2-2 X光單晶繞射......................................68 3-2-3 UV-Vis吸收光譜...................................73 3-2-4 Photoluminescence (PL)放光光譜.................75 3-2-5 循環伏安法.......................................76 第四章 結論.............................................79 第五章 參考文獻.........................................82 第六章 附錄.............................................86

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