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研究生:黃婉婷
研究生(外文):Wan-Ting Huang
論文名稱:α與β氰基PPV衍生物之合成與光學性質
論文名稱(外文):Synthesis and Optical properties of α- and β- cyano Poly(p-phenylenevinylene) Derivatives
指導教授:林木獅
指導教授(外文):Mu-Shin Lin
學位類別:碩士
校院名稱:國立交通大學
系所名稱:應用化學系
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:2002
畢業學年度:90
語文別:英文
論文頁數:70
中文關鍵詞:高分子有機發光二極體
外文關鍵詞:PLEDs
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我們合成以 thiophene-benzene-thiophene 為主體結構的共軛性分子,在苯環上加入長碳鏈,除了可以避免分子的堆疊外,也希望能增加分子的溶解度。並且分別在雙鍵的α與β位置導入拉電子 cyano 基團,期望能增加分子的電子傳輸能力。我們將討論,由於 cyano 基團在雙鍵上的位置不同,所造成不同程度的立體障礙,在光學性質上的影響。
我們選擇 PMMA 及 PVK 為host matrix材料。PMMA 與 PVK 具有光學及電化學不反應性,具有好的成膜能力及熱穩定性。PVK 同時扮演電洞傳輸材料及發光材料的角色。我們將討論將 α-TPT 與 β-TPT 分別 doping 在這兩種材料所造成的光學性質。並且改變 dopant 的濃度,觀察其變化。
雖然 α-TPT 與 β-TPT 具有相同的主鏈結構,但因為 cyano 基團所在的位置不同,而使這兩種材料的光學性質有極大的差異。β-TPT 的發光波長比 α-TPT 紅位移,而螢光強度也比 α-TPT 大。這是因為當cyano 基團位於α位置時,較靠近苯環及長碳鏈,所造成的立體障礙比較大,而扭轉角度大,造成共軛長度變短,分子共軛性被破壞,所以觀察到上述的實驗結果。
在摻混的實驗中,當 1wt% β-TPT 摻混在 PVK,可以得到最強的螢光強度。而所合成的 polymer ( P1與P2 ),因為 concentration effect 與 aggregation現象,使 polymer film相較於小分子而言,發光波長紅位移,並且螢光強度降低許多。

Two light-emitting molecules with the variation of cyano position and the corresponding polymers were synthesized, i.e., 2,5-Bis( 2-thienyl-1-cyanovinyl )-1-
( 2’-ethylhexyloxy ) -4-methoxybenzene (α-TPT ), 2,5-Bis( 2-thienyl-2-cyanovinyl )
-1-( 2’-ethylhexyloxy )-4-methoxybenzene (β-TPT ), poly[ 2,5-Bis( 2-thienyl-1-
cyanovinyl )-1- ( 2’-ethylhexyloxy )-4-methoxybenzene ] ( P1 ) and poly[2,5-Bis( 2-
thienyl-2-cyanovinyl )-1-( 2’-ethylhexyloxy )-4-methoxybenzene ] ( P2 ).
α-TPT and β-TPT, respectively, were blended into different host polymers, PMMA and PVK, to study the optical properties of the dopants in different host matrix. Althoughα-TPT and β-TPT have the same backbone structure, their optical properties are quite different with the variation of cyano position. The PL emission maximum (λmax ) of α-TPT was found blue-shifted, compared with that of β-TPT. The PL intensity of β-TPT was stronger than that of α-TPT. Concentration effect in the optical properties was found that 1 wt% of β-TPT in PVK had the maximum fluorescence emission.
The PL maximum peak wavelength for polymer films (P1 and P2 ) was red-shifted when compared with the polymer blends. The PL intensities for polymer film ( P1 and P2 ) were weaker than the polymer blends.

Abstract in Chinese............................................i
Abstract......................................................ii
Acknowledgments..............................................iii
Table of contents.............................................iv
List of Tables and Schemes....................................vi
List of Figures..............................................vii
CHAPTER 1 INTRODUCTION
1.1 Historical Evolution of OLEDs.............................1
1.2 Mechanism of Photoluminescence and Electroluminescence....4
1.3 Statement of The Problems.................................6
CHAPTER 2 EXPERIMENTAL
2.1. Materials................................................9
2.2. Instruments.............................................10
2.3. Synthestic Scheme of Model Compounds and Polymers.......11
2.4. Synthesis of 1-methoxy-4-( 2’-ethylhexyloxy )benzene
(1) ...................................................12
2.5. Synthesis of 1,4-Bis( bromomethyl )-2-( 2’-
ethylhexyloxy )-5- methoxybenzene ( 2 ).................12
2.6. Synthesis of 1,4-Bis( cyanomethyl )-2-( 2’-
ethylhexyloxy )-5- methoxybenzene ( 3 ).................13
2.7. Synthesis of 1,4-dicarboxyaldehyde-2-( 2’-
ethylhexyloxy )-5- methoxybenzene ( 4 ).................13
2.8. Synthesis of 2,5-Bis(2-thienyl-1-cyanovinyl)-1- (2’-
ethylhexyloxy)-4-methoxybenzene ( α-TPT )..............14
2.9. Synthesis of 2,5-Bis(2-thienyl-2-cyanovinyl)-1- (2’-
ethylhexyloxy)-4-methoxybenzene ( β-TPT )..............15
2.10. Synthesis of poly[ 2,5-Bis(2-thienyl-1-cyanovinyl)-1-
(2’-ethylhexyloxy)-4-methoxybenzene ] ( P1 )...........16
2.11. Synthesis of poly[2,5-Bis(2-thienyl-2-cyanovinyl)-1-
(2’-ethylhexyloxy)-4-methoxybenzene ] ( P2 )...........16
2.12. Preparation of Polymer Films............................17
CHAPTER 3 RESULTS AND DISCUSSION
3.1. 1H-NMR Characterization of Materials....................18
3.2. Mechanism...............................................19
3.2.1 The Synthesis of Compound ( 2 )........................19
3.2.2 The Synthesis of Compound ( 4 )........................20
3.2.3 The Synthesis of Compound α-TPT.......................20
3.2.4 The Mechanism of Polymerization........................21
3.3. Thermal Analysis of Model Molecules and Polymers........23
3.4. Molecular Weight of Polymers............................24
3.5. Polymerization by FeCl3.................................25
3.6. The Effect of Cyano Group...............................26
3.7. Optical Properties......................................27
3.7.1 In Solution............................................27
3.7.2 In Polymer Blends......................................31
3.7.3 Polymer Films..........................................36
CHAPTER 4 CONCLUSIONS........................................40
REFERENCE.....................................................41

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