臺灣博碩士論文加值系統

本篇論文利用吲哚苯並咪唑雙聚體(bis(indole-N-benzimidazole)) 及咔唑苯並咪唑雙聚體(bis(carbazole-N-benzimidazole)) 衍生物體為有機發光二極體中的主體材料，其中苯並咪唑具有促進電子傳遞及注入之特性，而咔唑本身則具有較高的三重態能階同時也具備良好的電洞傳導性質，因此選用此兩種分子做進一步的探討，而在之前的研究顯示，此兩種化合物利用碳氮鍵結相較於碳碳鍵結，碳氮鍵結可以使電子能有更佳分散效果，增加三重態能階，因此我們採用碳氮鍵結的方式來合成此系列化合物；另外，近年來吲哚在有機發光二極體之材料中也備受討論，因其同樣具有好的電洞傳遞能力以及高的三重態能階，因此本篇論文分為兩系列來討論，以這兩種傳電洞之材料在苯並咪唑(benzimidazole) 之不同位置做取代，討論位置對於整體材料之影響，同時增加化合物之分子量來提高熱穩定性。我們利用 X-ray 單晶繞射探討分子的排列及堆疊；以紫外-可見光光譜(UV-Vis)、螢光放射光譜(FL)、磷光放射光譜(Ph) 進行光物理性質探討；以循環伏安法(CV)、差式脈波伏安法(DPV) 進行電化學性質探討，並將所得之化合物作為主體發光材料摻混FIrpic 應用在藍色磷光有機發光二極體之元件製作上，而在元件的表現上，以化合物3dCBZB 為主體光材料的元件效率最佳，在電賀密度為20 mA/cm2 時的驅動電壓為6.70 V；於操作電壓為3.5V 時可達最大亮度16750 cd/m2、最大發光效率47.15 cd/A；於操作電壓為3V 時可達最大發光功率為46.57lm/W、最大外部量子效率達21.10 %。

In this thesis, we synthesized two series of compounds―
bis(indole-N-benzimidazole) and bis(carbazole-N-benzimidazole) as the host materials in OLED. In this bipolar system, carbazole and indole groups which have high triplet energy and good hole-transporting ability as the hole-transporting moiety, and benzimidazole as the electron-transporting moiety. Directly connect two moieties and compare the effect of different substituted position. In addition, we increase molecular weights to improve their thermal stability. We have been performed Ultraviolete-visible (UV-vis) spectral, photoluminescence (PL) spectral, cyclic voltammetry (CV), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) measurements to investigate the photophysical properties, thermal properties and electrochemical properties of these materials. The results show that all these host materials have excellent thermal stability and maintain high triplet energy.The blue PhOLED device used this thesis compound as the host material and the compound 3dCBZB existed the best performance than other compounds in the device dopant 18% FIrpic. It exhibited the turn-on voltage at 20 mA/cm2 was 6.70V, maximum luminance value (16750 cd/m2), the maximum current efficiency (47.15 cd/A), the maximum power efficiency (46.57 lm/W), and the maximum external quantum efficiency (20.01 %).

目錄
中文摘要................................................................................................................ IV
Abstract ...................................................................................................................V
化合物結構式與編號............................................................................................ VI
圖目錄..................................................................................................................VIII
表目錄.................................................................................................................... XI
流程目錄...............................................................................................................XII
第一章緒論 .......................................................................................................1
1.1 前言 .............................................................................................................. 1
1.2 有機發光二極體起源歷史.......................................................................... 2
1.3 有機發光二極體工作原理.......................................................................... 3
1.3.1 發光原理.......................................................................................... 3
1.3.2 元件架構.......................................................................................... 5
1.3.3 元件之工作原理.............................................................................. 6
1.4 主客摻混磷光發光系統.............................................................................. 7
1.4.1 電激磷光.......................................................................................... 7
1.4.2 主客摻混發光系統.......................................................................... 8
1.4.3 能量之淬熄...................................................................................... 9
1.5 有機發光二極體之材料............................................................................ 10
1.5.1 陽極材料........................................................................................ 10
1.5.2 陰極材料.........................................................................................11
1.5.3 電洞注入材料.................................................................................11
1.5.4 電洞傳輸材料................................................................................ 12
1.5.5 電子注入材料................................................................................ 13
1.5.6 電子傳導材料................................................................................ 14
1.5.7 主發光體材料................................................................................ 15
1.5.8 客體發光材料................................................................................ 16
1.6 近期藍色有機發光二極體發展................................................................ 17
第二章結果與討論.........................................................................................20
2.1 分子設計.................................................................................................... 20
2.2 合成策略與方法........................................................................................ 24
2.3 X-Ray 晶體結構分析................................................................................ 28
2.4 熱性質分析................................................................................................ 32
2.5 光物理性質分析........................................................................................ 35
2.6 電化學性質分析........................................................................................ 43
2.7 能量轉移.................................................................................................... 49
2.8 有機電激發光元件表現............................................................................ 53
第三章結論 ...........................................................................................................67
4.1 實驗儀器與試劑............................................................................................. 68
4.1.1 儀器部分.............................................................................................. 68
4.1.2 試劑與溶劑.......................................................................................... 69
4.2 合成步驟......................................................................................................... 70
參考文獻.................................................................................................................88
附錄一化合物 DSC 及TGA 圖..........................................................................95
附錄二化合物 X-ray 晶體參數表、鍵長與鍵角數據.......................................98
附錄三化合物之氫核磁共振光譜與碳核磁共振光譜.....................................137

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