臺灣博碩士論文加值系統

摘要 i
Abstract ii
誌謝 iii
目錄 iv
Figure索引 vi
Scheme索引 vii
Table索引 viii
第一章 緒論 1
1.1前言 1
1.1.1 IC半導體之應用 2
1.1.2 軟性印刷電路板之應用 2
1.1.3 液晶顯示器之應用 3
1.2聚醯亞胺的背景 4
1.3聚醯亞胺的合成 5
1.3.1一步法（one-step method） 7
1.3.2二步法（two-step method） 8
1.3.3以矽烷化二胺與二酸酐合成聚醯亞胺 9
1.4無色聚醯亞胺的合成(colerless polyimide,CPI) 11
1.4.1導入高電負度基團 12
1.4.2導入扭曲式結構或巨大側基 15
1.4.3導入脂環族(脂肪族)結構 17
1.5研究動機 24
第二章 實驗步驟 25
2.1實驗藥品 25
2.2實驗儀器 26
2.3單體合成 27
2.3.1 Tetramethyl bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylate (BHTE) 的合成 27
2.3.2 bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylic acid (BHTA)的合成 27
2.3.3 bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylic dianhydride (BHDA(xn),Exo, Endo)的合成 28
2.3.4 bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (BCDA)的合成 28
2.4高分子合成 29
2.5高分子薄膜製備 30
第三章 結果與討論 31
3.1單體合成與表徵 31
3.1.1 tetramethyl bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylate (BHTE)的合成與表徵 32
3.1.2 bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylic acid (BHTA)的合成與表徵 33
3.1.3 bicyclo[2,2,1]heptane-2,3,5,6-tetracarboxylic dianhydride (BHDA)的合成與表徵 35
3.1.4 bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (BCDA)的合成與表徵 37
3.2高分子合成與鑑定 41
3.3高分子分子量與溶解度 46
3.4高分子熱穩定性 48
3.5高分子機械性質 51
3.6高分子光學性質 52
3.7高分子介電性質 56
第四章 結論 57
Reference 58

1. Ni, H.-J.; Liu, J.-G.; Wang, Z.-H.; Yang, S.-Y., A review on colorless and optically transparent polyimide films: Chemistry, process and engineering applications. Journal of Industrial and Engineering Chemistry 2015, 28, 16-27.
2. Ando, S., Optical Properties of Fluorinated Polyimides and Their Applications to Optical Components and Waveguide Circuits. Journal of Photopolymer Science and Technology 2004, 17, 219-232.
3. Zhuang, Y.; Seong, J. G.; Lee, Y. M., Polyimides containing aliphatic/alicyclic segments in the main chains. Progress in Polymer Science 2019, 92, 35-88.
4. Park, C.-Y.; Kim, E.-H.; Kim, J. H.; Lee, Y. M.; Kim, J.-H., Novel semi-alicyclic polyimide membranes: Synthesis, characterization, and gas separation properties. Polymer 2018, 151, 325-333.
5. 金進興, 軟性電路板材料全書. 台灣電路板協會: 2007.
6. Li, F.; Harris, F. W.; Cheng, S. Z. D., Polyimide films as negative birefringent compensators for normally white twisted nematic liquid crystal displays. Polymer 1996, 37, 5321-5325.
7. Bogert, M. T.; Renshaw, R. R., 4-Amino-o-Phthalic Acid and Some of Its Derivatives.1. Journal of the American Chemical Society 1908, 30, 1135-1144.
8. Laszlo, E. A. Process for preparing polyimides by treating polyamide-acids with lower fatty monocarboxylic acid anhydrides. US3179630A, 1965.
9. Murray, E. W. Polyamide-acids, compositions thereof, and process for their preparation. US3179614, 1965.
10. Vinogradova, S. V. V., Ya S.; Korshak, V. V., Some features of the synthesis of polyimides by single-stage high-temperature polycyclization. Polymer Science U.S.S.R. 1970, 12, 2254-2262.
11. Suzuki, H.; Abe, T.; Takaishi, K.; Narita, M.; Hamada, F., New Polyimides Derived from Norbornanetetracarboxylic Dianhydride and Aromatic Diamine Showing Excellent Transparency and Heat-Resistance. International Journal of the Society of Materials Engineering for Resources 2000, 8, 9-14.
12. Harris, F. W.; Feld, W. A.; Lanier, L. H. In Structure-solubility relationships in aromatic polyimides, American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 1976; 353-358.
13. Liaw, D.-J.; Liaw, B.-Y., Synthesis and Properties of Polyimides Derived from 1,4-Bis(4-aminophenoxy)-2-tert-butylbenzene. Polymer Journal 1996, 28, 970-975.
14. Hsiao, S.-H.; Yang, C.-P.; Chen, S.-H., Synthesis and properties ofortho-linked aromatic polyimides based on 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene. Journal of Polymer Science Part A: Polymer Chemistry 2000, 38, 1551-1559.
15. Malinge, J.; Garapon, J.; Sillion, B., New developments in polybenzhydrolimide resins: Application in the field of heat resistant coatings, adhesives and laminates. British Polymer Journal 1988, 20, 431-439.
16. Liaw, D.-J.; Liaw, B.-Y.; Yu, C.-W., Synthesis and characterization of new organosoluble polyimides based on flexible diamine. Polymer 2001, 42, 5175-5179.
17. Hergenrother, P. M.; Havens, S. J., Polyimides Containing Quinoxaline and Benzimidazole Units. Macromolecules 1994, 27, 4659-4664.
18. Butt, M. S.; Akhtar, Z.; Zafar-uz-Zaman, M.; Munir, A., Synthesis and characterization of some novel aromatic polyimides. European Polymer Journal 2005, 41, 1638-1646.
19. Cho, Y. J.; Park, H. B., High Performance Polyimide with High Internal Free Volume Elements. Macromolecular Rapid Communications 2011, 32, 579-586.
20. Liaw, D.-J.; Wang, K.-L.; Huang, Y.-C.; Lee, K.-R.; Lai, J.-Y.; Ha, C.-S., Advanced polyimide materials: Syntheses, physical properties and applications. Progress in Polymer Science 2012, 37, 907-974.
21. Hasegawa, M., Development of Solution-Processable, Optically Transparent Polyimides with Ultra-Low Linear Coefficients of Thermal Expansion. Polymers (Basel) 2017, 9.
22. Guo, Y.-Z.; Shen, D.-X.; Ni, H.-J.; Liu, J.-G.; Yang, S.-Y., Organosoluble semi-alicyclic polyimides derived from 3,4-dicarboxy-1,2,3,4-tetrahydro-6-tert-butyl-1-naphthalene succinic dianhydride and aromatic diamines: Synthesis, characterization and thermal degradation investigation. Progress in Organic Coatings 2013, 76, 768-777.
23. Kreuz, J. A., Hydrolyses of polyamic-acid solutions. Journal of Polymer Science Part A: Polymer Chemistry 1990, 28, 3787-3793.
24. Watanabe, Y.; Sakai, Y.; Shibasaki, Y.; Ando, S.; Ueda, M.; Oishi, Y.; Mori, K., Synthesis of Wholly Alicyclic Polyimides from N-Silylated Alicyclic Diamines and Alicyclic Dianhydrides. Macromolecules 2002, 35, 2277-2281.
25. 丁孟賢, 聚醯亞胺-化學、結構與性能的關係及材料. 科學出版社: 2012.
26. Elliott, R. F. Polyamide-acids and polyimides from hexafluoropropylidine bridged diamine. US3356648, 1967.
27. Hougham, G.; Tesoro, G.; Shaw, J., Synthesis and Properties of Highly Fluorinated Polyimides. Macromolecules 1994, 27, 3642-3649.
28. Harris, F. W.; Hsu, L.-C.; Tso, C. C., Synthesis and characterization of polyimides based on 2, 2′-bis (trifluoromethyl)-4, 4′-diaminobiphenyl. In American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 1990; Vol. 31, pp 342-343.
29. Matsuura, T.; Hasuda, Y.; Nishi, S.; Yamada, N., Polyimide derived from 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl. 1. Synthesis and characterization of polyimides prepared with 2,2'-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride or pyromellitic dianhydride. Macromolecules 1991, 24, 5001-5005.
30. Hsiao, S.-H.; Wang, H.-M.; Chen, W.-J.; Lee, T.-M.; Leu, C.-M., Synthesis and properties of novel triptycene-based polyimides. Journal of Polymer Science Part A: Polymer Chemistry 2011, 49, 3109-3120.
31. Liu, J.; Chen, G.; Mushtaq, N.; Fang, X., Synthesis of organosoluble and light-colored cardo polyimides via aromatic nucleophilic substitution polymerization. Polymers for Advanced Technologies 2015, 26, 1519-1527.
32. Matsumoto, T., Aliphatic Polyimides Derived from Polyalicyclic Monomers. High Performance Polymers 2001, 13, S85-S92.
33. Walter, M., Edwards; Robinson, I., Maxwell Polyimides of pyromellitic acid. US2710853, 1953.
34. William F Gresham, J. M. A. N. Polyimide intermediates. US2712543, 1954.
35. William, F., Gresham,Jr Marcus, A, Naylor Novel polyimides. US2731447, 1954.
36. Tabushi, I.; Tanitpura, N.; Oda, R., Polyimides from Some Alicyclic Tetracarboxylic Acids Obtained by Addition-Cyclizations. The Journal of the Society of Chemical Industry, Japan 1964, 67, 1084-1086.
37. Uchida, A.; Hasegawa, M.; Manami, H., Cis,cis,cis-1,2,4,5-cyclohexanetetracarboxylic acid and its dianhydride. Acta Crystallogr C 2003, 59, o435-8.
38. Hasegawa, M.; Hirano, D.; Fujii, M.; Haga, M.; Takezawa, E.; Yamaguchi, S.; Ishikawa, A.; Kagayama, T., Solution-processable colorless polyimides derived from hydrogenated pyromellitic dianhydride with controlled steric structure. Journal of Polymer Science Part A: Polymer Chemistry 2013, 51, 575-592.
39. Hasegawa, M.; Fujii, M.; Ishii, J.; Yamaguchi, S.; Takezawa, E.; Kagayama, T.; Ishikawa, A., Colorless polyimides derived from 1S,2S,4R,5R-cyclohexanetetracarboxylic dianhydride, self-orientation behavior during solution casting, and their optoelectronic applications. Polymer 2014, 55, 4693-4708.
40. Itamura, S.; Yamada, M.; Tamura, S.; Matsumoto, T.; Kurosaki, T., Soluble polyimides with polyalicyclic structure. 1. Polyimides from bicyclo[2.2.2]oct-7-ene-2-exo,3-exo,5-exo,6-exo-tetracarboxylic 2,3:5,6-dianhydrides. Macromolecules 1993, 26, 3490-3493.
41. Chun, B.-W., Preparation and characterization of organic-soluble optically transparent polyimides from alicyclic dianhydride, bicyclo[2.2.2]-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride. Polymer 1994, 35, 4203-4208.
42. Matsumoto, T.; Kurosaki, T., Soluble and Colorless Polyimides from Bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic 2,3:5,6-Dianhydrides. Macromolecules 1997, 30, 993-1000.
43. Chow Sui-Wu, J.; Whelan, J. M. Method for producing polyimides from diamines and di-acd di-ester derivatives of danhydrides. US3037966, 1962.
44. Matsumoto, T.; Kawabata, S.; Takahashi, R., Alicyclic Polyimides based on bicyclo[2.2.1]heptane- 2,3,5,6-tetracarboxylic 2,3-5,6-dianhydrides. High Performance Polymers 2006, 18, 719-726.
45. Kusama, M.; Matsumoto, T.; Kurosaki, T., Soluble Polyimides with Polyalicyclic Structure.3. Polyimides from (4arH,8acH)-Decahydro-1t,4t:5c,8c-dimethanonaphthalene- 2t,3t,6c,7c-tetracarboxylic 2,3:6,7-Dianhydride. Macromolecules 1994, 27, 1117-1123.
46. Matsumoto, T., Nonaromatic Polyimides Derived from Cycloaliphatic Monomers1. Macromolecules 1999, 32, 4933-4939.
47. 徐寧霜. 脂環族二酸酐與聚醯亞胺之合成與表徵. 碩士論文, 國立台灣科技大學, 2019.
48. James, D. E.; Stille, J. K., The palladium(II) catalyzed olefin carbonylation reaction. Mechanisms and synthetic utility. Journal of the American Chemical Society 1976, 98, 1810-1823.
49. Yamada, M.; Kusama, M.; Matsumoto, T.; Kurosaki, T., Synthesis of bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic 2,3:5,6-dianhydrides. The Journal of Organic Chemistry 1992, 57, 6075-6077.
50. DeCamp, M. R.; Landon, B. J., On the dehydration of trans-1,2-dihydrophthalic acid. Tetrahedron Letters 1980, 21, 3231-3234.
51. 王建淳. 脂環族二酸酐與其聚醯亞胺之合成技術開發. 碩士論文, 國立台灣科技大學, 2017.