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研究生: 溫雅蘭
Wen, Ya-Lan
論文名稱: 電子材料中芳香烯酮聚合物的合成與性質之探討
Studies on the Synthesis and Properties of Arylidenone Polymer in Electronic Material
指導教授: 申永輝
Shen, Yun-Hwei
溫紹炳
Wen, Shaw-Bing
學位類別: 博士
Doctor
系所名稱: 工學院 - 資源工程學系
Department of Resources Engineering
論文出版年: 2012
畢業學年度: 100
語文別: 中文
論文頁數: 99
中文關鍵詞: 聚酯醯亞胺芳香醯酮聚合物發光旋環雙芴
外文關鍵詞: poly(ester-imide), luminescent, spirobifluorene
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  • 聚醯亞胺(PI)在顯示器上的貢獻,倍受學界及產業界的注目,然此種電子材料仍有一些溶解度的問題需要克服。聚酯醯亞胺不僅改善了聚醯亞胺溶解度及加工性不佳的缺點,並且保有聚醯亞胺的熱穩定性佳等優點,是著名的高性能高分子材料。本論文使用直接聚縮合法及低溫溶液聚合法,將含有醯亞胺的單體及雙胺或雙醇合成聚酯醯亞胺,並將孤立發光團1,3,4-二唑及芴基導入,使溶解度有所提升。
    芳香醯酮聚合物的結構由NMR及IR光譜分析,還有光學性質、溶解度、熱分析和X-ray分析其不同性質與討論結果。帶有發光旋環雙芴的聚酯醯亞胺衍生物具有相當高的玻璃轉換溫度和極佳的熱穩定度,兩種衍生聚合物以螢光放射光譜(PL)測定均放出藍綠光,放射出的最大值約400-600nm。含芴聚合物的電子親和力約2.75-2.84eV;氧化還原電位分析顯示具有可逆氧化及不可逆還原,也就是n-type光電材料。
    使用介面聚合反應製備芳香醯酮類的液向型液晶聚合體,所有聚合物性質以NMR及IR光譜分析,還有光學性質、溶解度、熱分析和X-ray分析其不同性質與討論結果。由熱分析結果顯示這些共聚物具有良好的熱穩定性,熱重損失10%的溫度大約在348-370℃之間。

    Polyimides (PI) have recently attracted attention of their potential use in display technology, and then intrigued interests in both academic and industrial circles. However, electronic materials have some solubility need further improvement. Poly (ester-imide)s are well known as high performance polymeric materials Those modified polyimides not only improve processability and solubility, but also exhibit excellent thermal stability. In this study, poly(ester-imide)s have preparated by direct polycondensation at low temperature in polymerization from imide-containing monomers and diol or diamine, and 1,3,4-oxadiazole and fluorene moieties by introducing into targeted molecules to promote solubility.
    The structure of arylidenone polymer was confirmed by NMR and IR spectral analyses. The various characteristics of the resulting polymers including optical properties, solubility, thermal analysis, and X-ray diffraction analysis were determined and discussed. The luminescent poly(ester-imide)s derivatives based on spirobifluorene rings in the main chain showed relatively high glass-transition temperatures (about 160 °C) and good satisfactory thermal stability. Two polymers emitted blue-greenish light with photoluminescence (PL) emission maxima around 400–600 nm and the electron affinity of new polymers was estimated as 2.75–2.84 eV. Cyclic voltammetry displayed polymers had reversible oxidation and irreversible reduction, making them n-type electroluminescent materials.
    The lyotropic LCPs of arylidenone polymer were prepared by interfacial polycondensation reaction. All these polyesters were confirmed by NMR and IR spectral analyses. The various characteristics of the resulting polymers including optical properties, solubility, thermal analysis, and X-ray diffraction analysis were determined and discussed. Thermogravimetric studies revealed that these polyesters have fairly good thermal stability, thermal degradation reactions were found 10% weight loss in the temperature range of 348-370℃。

    中文摘要……………………………………………………………………I 英文摘要……………………………………………………………………II 誌謝…………………………………………………………………………IV 目錄…………………………………………………………………………V 表目錄………………………………………………………………………VII 圖目錄………………………………………………………………………VIII 第一章 緒論…………………………………………………………………1 1-1 前言……………………………………………………………………1 1-2 聚醯亞胺之介紹………………………………………………………5 1-3 聚醯亞胺作為軟性材料基板之介紹…………………………………11 1-4 有機發光二極體OLED及PLED材料之介紹…………………………13 1-5 芳香烯酮類之介紹……………………………………………………20 1-6 高分子液晶之介紹……………………………………………………21 1-7 研究動機與目的………………………………………………………24 第二章 含芳香烯酮之聚酯醯亞胺的合成…………………………………25 2-1 含芳香醯酮之聚酯醯亞胺合成方法簡介……………………………25 2-2 實驗方法與步驟………………………………………………………27 2-2-1 使用儀器介紹………………………………………………………28 2-2-2 醯酮原料製備………………………………………………………31 2-2-3 二醯亞胺二羧酸單體的合成………………………………………32 2-2-4 聚酯醯亞胺的合成…………………………………………………37 2-3 結果與討論……………………………………………………………42 2-3-1 NMR及FT-IR ………………………………………………………42 2-3-2 X-ray分析…………………………………………………………49 2-3-3 高分子熱性質分析…………………………………………………53 2-3-4 溶解度測試…………………………………………………………66 2-4 光電性質研究…………………………………………………………69 2-4-1 UV/Vis吸收光譜分析……………………………………………69 2-4-2 溶液態光激發螢光放射光譜分析…………………………………72 2-4-3 電化學性質探討……………………………………………………74 第三章 含芳香烯酮之高分子液晶的合成………………………………81 3-1 含芳香烯酮之高分子液晶的合成方法簡介…………………………81 3-2 實驗方法與步驟………………………………………………………82 3-3 結果與討論……………………………………………………………85 3-3-1 NMR及FT-IR ……………………………………………………85 3-3-2 X-ray分析…………………………………………………………87 3-3-3 高分子熱性質分析…………………………………………………88 3-3-4 溶解度測試…………………………………………………………92 第四章 結論…………………………………………………………………93 第五章 參考文獻……………………………………………………………96

    1. W. M. Edwards; I. M. Robinson; 1955, British Pat. 570858; U. S. Pat. 2710853
    2. K. Faghihi; M. Hajibeygi ; J. Appl. Polym. Sci., 2004, 92, 3447
    3. C. P. Yang; R. S. Chen; M. F. Hsu; J. Appl. Polym. Sci., 2003, 88, 669
    4. K. Faghihi; H. Naghavi1; J. Appl. Polym. Sci., 2005, 96, 1776
    5. D. J. Liaw; C. L. Fan; C. C. Lin; K. L. Wang; J. Appl. Polym. Sci., 2004, 92, 2486
    6. C. P. Yang; Y. P. Chen; E. M. Woo; J. Polym. Sci. Part A: Polym. Chem., 2004, 42, 3116
    7. Z. Chi; D. Cheng; X. Pan; Y. Zhang; J. Xu; H. Bu; Polymer, 2005, 46, 5840
    8. 劉挺中, ”主鏈含噻吩及馬來醯西亞胺衍生物高分子的合成與光學性質”,國立成功大學化學工程研究所碩士論文,民國94年.
    9. D. C. Shin; J. H. Ahn; Y. H. Kim; S. K. Kwon, J. Polym. Sci. Part A: Polym. Chem., 2000, 38, 3086
    10. S. Liu; X. Jiang; H. Ma; M. S. Liu; A. K. Y. Jen; Macromolecules, 2000, 33, 3514
    11. J. Li; D. Liu; Y. Li; C. S. Lee; H. L. Kwong; S. Lee; Chem. Mater., 2005, 17, 1208
    12. M. Grell; D. D. C. Bradley; G. Ungar; J. Hill; K. S. Whitehead; Macromolecules, 1999, 32, 5810
    13. M. T. Rogert, R. R. Renshaw, J. Am. Chem. Soc. 1980, 30, 1135
    14. W. N. Edwards, U.S. Patent 3, 1965, 179, 614
    15. A. E. Endry, U.S. Patent 3, 1965, 179, 630
    16. C. E. Sroog; Macromolecular Reviews, 1976, 11, 172
    17. D. F. Loncrini, J. Polym. Sci. 1966, 4, 1531
    18. J. G. Malvaney, J. Polym. Sci. Part A: Polym. Chem. 1986, 24, 613
    19. C. P. Yang, G. S. Liou, R. S. Chen, C. Y. Yang, J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 1090
    20. S. K. Dolui, D. Pal, S. Maiti, J. Appl. Polym. Sci. 1985, 30, 3867
    21. S. Maiti, S. Das, J. Appl. Polym. Sci. 1981, 26, 957
    22. S. Maiti, S. Das, Angew Makromol. Chem. 1980, 86, 181
    23. W. M. Edwards; I. M. Robinson; 1955, British Pat. 570858; U. S. Pat.
    2710853
    24. S. Yasuda; G. C. Wu; H. Tanakn; K. Sanui; N. Ogata; J. Polymer Sci.: Polymer Chem. Ed., 1983, 21, 2609
    25. G. C. Wu; H. Tanaka; K. Sanui; S. Yasuda; Polym. J., 1981, 13, 989
    26. F. Higashi; A. Kobayashi; H. Shimazaki; J. Polym. Sci. Part A: Polym. Chem., 1993, 31, 1301
    27. T. C. Hung; T. C. Chang; J. Polym. Sci. Part A: Polym. Chem., 1996, 34, 2455
    28. 洪金賢, 工業材料雜誌, 2007, 243, 159
    29. 蘇水祥, 橫山明聰, 朱健慈, 江俊德, 科學發展, 2001, 349, 38
    30. M. Pope, H. P. Kallman, P. Mangnante, J. Chem. Phys. 1963, 38; 2042
    31. P. S. Vincett, W. A. Barlow, R. A. Hann, G. G. Roberts, Thin Solid Films, 1982, 171, 94
    32. C. W. Tang, S. A. Vanslyke, Appl. Phys. Lett. 1987, 51, 913
    33. R. H. Partridge, Polymer, 1983, 24, 733
    34. H. Burroughes, D. D. C. Bradley, A. R. Brown, N. Marks, K. Mackay, R.H. Friend, P. L. Burns, A. B. Holmes, Nature, 1990, 347, 539
    35. Y. Ohmori, M. Uchida, K. Muro., K. Yoshino, Jan. J. Appl. Phys. 1991, 30, L1941
    36. G. Grem, G. Leditzky, B. Ullrich, G. Leising, Adv. Mater. 1992, 4, 36
    37. D. Braun, A. J. Heeger, Appl. Phys. Lett. 1991, 58, 1982
    38. S. Doi, M. Kuwabara, T. Noguchi, T. Ohnishi, Synth. Met. 1993, 57, 4174
    39. Z. Yang, I. Sokolik, F. E. Karasz, Macromolecules, 1993, 26, 1188
    40. S. H. Lee, T. Nakamura, T. Tsutsui, Org. Lett. 2001, 3, 2005
    41. K. Faghihi; M. Hajibeygi ; J. Appl. Polym. Sci., 2004, 92, 3447
    42. 侯豪情, 李悅生, 丁孟賢, 全國高分子論文學術報告(大陸合肥), 1997
    43. P. Sakthivel; P. Kannan; J. Polym. Sci Part A: polym. Chem., 2004, 42, 5215
    44. M. Murali; A. B. Samui; J. Polym. Sci Part A: polym. Chem., 2006, 44, 53
    45. P. P. Manish; J. Polym. Mater., 1999, 16, 6
    46. K. A. Aly; A. S. Hammam; Eur. Polym. J., 2000, 36, 1933
    47. 陳俊元, “含萘液晶之合成及性質研究”國立成功大學化學工程研究所碩士論文, 民國91年
    48. 松本正一, 角田市良; 液晶之基礎與應用, 民國85年

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