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研究生:張進傳
研究生(外文):Chin-Chuan Chang
論文名稱:三苯胺化合物之合成、性質探討與有機發光元件上應用
論文名稱(外文):Synthesis and Characterization of Triphenylamine Derivatives, and Their Applications on Organic Light Emitting Diode
指導教授:梁文傑梁文傑引用關係
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:英文
論文頁數:208
中文關鍵詞:三苯胺紅光染料電洞傳導有機發光元件
外文關鍵詞:triphenylaminered dyehole transportorganic light emitting device
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由於三苯胺同時具有電化學活性和電洞傳導特性, 我們希望引入三苯胺基團來合成紅光材料與電洞傳導材料 , 並提高有機發光元件的效率及應用範圍.

在第二章中, 我們以三苯胺作為取代基團合成紅光染料1, 並從電化學及Förster能量轉移的角度來討論染料在之有機發光元件的表現, 且獲得一具有62000/m2的高亮度元件, 其最高效率可達2.9cd/A. 且已發表在Organic Lett. 2006, 8, 2623-2626.

第三章中, 我們以三苯胺做為取代基團合成具有光阻活性的高分子Polymer 1 和Polymer 2. 由於三苯胺具有兩項主要功能 (1) 電化學聚合交聯光阻高分子 (2) 電洞傳導功能. 利用電化學聚合, 高分子會沉積在導電玻璃ITO上; 再利用紫外線曝光顯影, 交聯的高分子能夠被選擇性的分解, 並用來製作具有特定放光區域的有機發光元件. 並發表在Chemistry of Materials. 2008, 20, 5816-5821.

最後, 我們藉由表面自組裝的方式將三苯胺聚合在導電玻璃ITO上, 利用電化學聚合, 能將三苯胺轉換成雙三苯胺分子來提高表面的電洞傳導活性. 並觀察表面高分子梳的電化學(electrochemistry), 紫外線-可見光吸收光譜(UV-Vis absorption), 水接觸角(Water Contact Angle)及掃描式電子顯微鏡(SEM)分析. 將高分子梳運用在發光元件上, 可以獲得一具有16200 cd/m2 和 20.9 cd/A的發光元件. 最後, 利用光化學氧化的方式將三苯胺氧化, 可以獲得具有圖樣(patterned)的有機發光元件.
Tirphenylamine is good a hole transport material with electrochemistry activity. We hope to use this moiety to synthesis triphenylamine derivatives to improve the performance of OLED, including red light emitting materials, hole transport materials.

In chapter 2, the physical of red light emitting PCF dye 1 was discussed with electrochemistry, Förster energy transfer, and OLED devices. The dye-doped organic light-emitting diode shows red electroluminescence with the efficiency of 2.9 cd/A at 100 cd/m2 and maximum brightness of 62000 cd/m2. This chapter had published in Organic Lett. 2006, 8, 2623-2626

In chapter 3, we had synthesized a photo-labile organic semi-conducting polymer 1 and polymer 2 with triphenylamine moiety with photo resistance type property. The triphenylamine group served as two functions: (1) cross-linking the polymer through electro-polymerization (2) hole transport material. After UV illumination, the polymer can be selectivity dissolution; we also demonstrated an image with PLED device. This chapter had published in Chemistry of Materials. 2008, 20, 5816-5821.

Finally, We use nitroxide SAM to serve as surface initiator, then growth triphenylamine polymer brush on ITO . After electro-polymerization, triarylamine polymer brushes can be dimerized and cross-link for hole transport enhancement. Surface analysis of cyclic voltammetry, UV-Vis absorption, water contact angle, and SEM had been studied in this chapter. The PLED device was optimized to 16200cd/m2 and 20.9cd/A. Through photo oxidation, polymer brushes can be selectively degradation to prepare a patterned PLED emitting device.
Contents
Chapter 1 Introduction…………………………………………………………… .….1
1-1 Introduction……………………………………………………………………..…1
1-1 Thesis introduction……………………………………………………………...…1
1-1-1 DCM red light materials………………………………………………….......3
1-1-2 Electro-polymerization of triphenylamine materials…………………………7
1-1-3 Surface modification of triphenylamine polymer……………………...…..11
1-2 Basic properties of triphenylamine-based materials…………..…………….….13
1-2-1 Morphology of triphenylamine-based material………………………..….14
1-2-2 Hole transport property of triphenylamine-based materials……………...17
1-2-3 Electro Chemical property of triphenylamine-based materials……………..21
1-2-4 Application of triphenylamine-based materials……………………………..26
1-2-4-1 OPVs……………………………………………………………..…….26
1-2-4-2 OFETs……………………………………………………………….…28
1-2-4-3 Photochromic……………………………………………………….….29
1-2-4-4 OLEDs…………………………………………………………….……30
1-2-4-4-1 Triphenylamine-based hole-transporting materials……………….31
1-2-4-4-2 Triphenylamine-based emitting materials………………………...32
1-3 Thesis themes………………………………………………………….…………34

Chapter 2 Triphenylamime substitute OLED Red Dye Material……………..……...35
2-1 Introduction………………………………………………………………………37
2-2 Result and Discussion……………………………………………………………42
2-2-1 Synthesis……………………………………….……………………………42
2-2-2 Electro-chemistry and UV-Vis absorption Analysis………………………..44
2-2-3 OLED devices fabrication and discussion……………………………….….48

Chapter 3 Synthesis of Photo-Resistance type Triphenylamime Hole Transport Polymers………………………………...……………...…………….…59
3-1 Introduction…………………………………………………………………...….59
3-2 Result and discussion……………………………………………………………63
3-2-1 Synthesis……………………………………………………………….……64
3-2-2 Electro-chemistry and UV-Vis absorption Analysis……….……………….66
3-2-3 PLED devices fabrication and discussion……………………………...……74
3-2-4 SEM image and Photo-Lithography application………………………...….77

Chapter 4 Surface Modification of Triphenylamine Polymer Brush, and their Application on PLED Devices…………………………..…………….......81
4-1 Introduction…………………………………………………………………...….81
4-2 Result and discussion……………………………………………………………89
4-2-1 Synthesis……………………………………………………………….……89
4-2-2 Water contact angle………………………………………………………….93
4-2-3 Electroc-hemistry and UV-Vis absorption Analysis………….…………….94
4-2-4 SEM Image of Polymer Brush………………………………………………98
4-2-5 PLED devices fabrication and discussion……………………………...…100
4-2-6 Application of Polymer Brush on Photo Imaged PLED devices…………104

Chapter 5 Conclusion………………………………...…………………………..…109

Chapter 6 References……………………………………...………………………...111
Chapter 7 Experimental Section………………………………………………….....123
7-1 Experimental Instruments and Chemical………………………………….123
7-2 Synthesis procedure…………………………………………………………..126
7-3 OLED and PLED Devices Data……………….…………………………...…...144
7-4 NMR data……………………………………………………………………….165
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