| 研究生: |
張宏德 Chang, Hung-Te |
|---|---|
| 論文名稱: |
含芳香環取代基的聚對位苯基乙烯系
衍生物之合成及其光電性質之研究 Studies on the Synthesis and Opto-Electronic Properties of Aryl-Substituted Poly(p-phenylenevinylene) Derivatives |
| 指導教授: |
葉茂榮
Yeh, Mou-Yung |
| 學位類別: |
博士 Doctor |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2007 |
| 畢業學年度: | 95 |
| 語文別: | 中文 |
| 論文頁數: | 106 |
| 中文關鍵詞: | 聚對位苯基乙烯系衍生物 |
| 外文關鍵詞: | PPV derivatives |
| 相關次數: | 點閱:99 下載:1 |
| 分享至: |
| 查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
本論文主要是以Gilch方法合成五種具有螢光性的PPV衍生物:Poly[2-decyloxy-1,4-phenylenevinyl- ene, DO-PPV] (P0)、Poly[2-decyloxy-5- (2'-(6'-dodecy loxy)naphthyl)-1,4-phenylenevinylene, DDN-PPV] (P1)、Poly- [2-decyloxy-5-(2',5'-bis(decyl- oxy)phenyl)-1,4-phenylenevinylene, DBDP- PPV] (P2)、Poly[2-decyloxy-5-(4’-ethoxyphenyl)-1,4-phen ylenevinylene, DEP-PPV] (P3)、Poly[2-decy- loxy-5-(4¢-tert-butylphenyl)-1,4-phenylene vinylene, DtBP-PPV] (P4)。除了P0不具有芳香環取代基外,在結構上P0~P4相似。利用質子核磁共振譜(1H NMR)、傅立葉轉換紅外線光譜 (FT-IR) 、紫外線與可見光吸收光譜(UV/Vis)、熱重量分析儀(TGA)、螢光放射光譜(PL)及電激發螢光放射光譜(EL)來探討所合成的聚合物(P0~P4)的結構、光的吸收及放射、熱及光電性質。
由於聚合物P0產生光氧化作用,使其在傅立葉轉換的紅外線光譜分析中,發現存有羰基(carbonyl group, -C=O)的結構;但P1~P4在傅立葉轉換的紅外線光譜分析中則沒有羰基吸收帶。在1H NMR分析中,顯現P0在結構上具有參鍵-雙-苄基(tolane-bis-benzyl,TBB)的缺陷,P1~P4則沒有TBB缺陷。由於P1~P4聚合物均具有共振性的芳香環取代基及不具有TBB缺陷,使得P1~P4在溶液狀態下的紫外線與可見光吸收波長(UV/Vis)及光激發的螢光放射波長(PL),與P0相較皆呈現紅位移現象。
以P0~P4為發光材料,分別組裝成電激發光元件,元件結構為ITO/PEDOT/PPVs/Ca/Ag。比較各元件電激發光特性,以P4為發光材料的元件顯現具有較低的驅動電壓(8.2 伏特)、較長的電激發光波長(546 nm) 、較高的亮度和發光效率。P4的元件在12伏特(v)時,其最大發光亮度和發光效率分別為57 cd/m2 和 0.112 cd/A。
Five fluorescent polymers, poly[2-decyloxy-1,4-phenylenevinylene, DO-PPV] (P0)、poly[2-
decyloxy-5-(2'-(6'-dodecyloxy)naphthayl)-1,4-phenyl- enevinylene, DDN-PPV] (P1)、poly[2-decyloxy-5-(2',5'-bis(decyloxy)phen- yl)-1,4-phenyleneviny- lene, DBDP-PPV] (P2)、poly[2-decyloxy-5-(4’-eth-oxy phenyl)-1,4-phenylene vinylene, DEP-PPV] (P3) and poly[2-decyloxy-5-(4¢-tert-butylphenyl)-1,4-phenylenevinylene, DtBP-PPV] (P4), are prepared by a method similar to the Gilch procedure in this stydy. The P0~P4 have a similar structure except that the P0 doesn’t have the conjugated aryl substituent. The structure and optical, fluorescent, thermal and opto-electronic properties of the poly(p-phenylenevinylene) derivatives (P0~P4) are characterized using proton nuclear magnetic resonance (1H NMR) spectrometry, fourier transform infrared (FT-IR) spectrum, ultraviolet and visible light (UV/Vis) absorption spectroscopy, thermogravimetric analysis (TGA), photoluminescence (PL), and electroluminescence (EL).
FT-IR spectra show the presence of carbonyl group in the P0 arised from the photooxidation, but no carbonyl group in P1~P4. 1H NMR spectra show the presence of tolane-bis-benzyl (TBB) structure defects in the P0, but no TBB defects in P1~P4. Owing to the presence of the conju- gated aromatic nucleus substituent and no TBB defects in the P1~P4, both UV/Vis absorp- tion peak and PL emission one of the P1~P4 solutions exhibit a red shift phenomenon as compared with those of the P0 solution.
With the P0~P4 acting as light-emitting polymers separately, the EL devices are fabricated with a sequential lamination of ITO/PEDOT/PPVs/Ca/Ag. The P4-based device shows a lower turn-on voltage (8.2 voltage), a longer EL emission wavelength (546 nm), and a higher brightness and luminescence efficiency as compared with the other PPVs-based device. The maximum brightness and luminescence efficiency of the P4-based device are 57 cd/m2 and 0.112 cd/A at an applied voltage of 12 V.
1. 張淑美;科學月刊,科學月刊雜誌社,台北,374期,P.106,2001年
2月號。
2. 劉佳明、翁文國、陳良吉;科學月刊,科學月刊雜誌社,台北,374
期,P.116,2001年2月號。
3. G. Destriau, J. Chem. Phys., 33, 587, 1936.
4. H. Ohnishi, Ann. Rev. Mater. Res., 19, 83, 1989.
5. S. Matsumoto, editor. Electronic display devices, Wiley, New York, Chapt
5, P.180, 1990.
6. M. Pope, H.P. Kallmann, P. Magnante, J. Chem. Phys., 38(8), 2042, 1963.
7. W. Helfrich, W.G. Schneider, Phys. Rev. Lett., 14(7), 229, 1965.
8. W. Helfrich, W.G. Schneider, J. Chem. Phys., 44(8), 2902, 1966.
9. P.S. Vincett, W.A. Barlow, R.A. Hann, G.G. Roberts, Thin Solid Films, 94,
476, 1982.
10. R.H. Partridge, Polymer, 24(6), 733, 1983.
11. C.W. Tang, S.A. Van Slyke, Appl. Phys. Lett., 51(12), 913, 1987.
12. C. Adachi, S. Tokito, T. Tsutsui, S. saito, Jpn. J. Appl. Phys., 27(2),
219, 1988.
13. C. Adachi, T. Tsutsui, S. Saito, Appl. Phys. Lett., 55(15), 1489, 1989.
14. J. Kido, M. Khodo, K. Okuyana, K. Nagai, Appl. Phys. Lett., 61(7),
761, 1992.
15. J. Kido, K. Hongavwa, M. Khoda, K. Nagai, K. Okuyama, Jpn, J. Appl.
Phys., 31(7B), 960, 1992.
16. D. Cleary, Polymer technology-after years in the dark, electric plastic
finally shines, 263(5139), 1700~1702, since 1994.
17. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K.Mackay,
R.H. Friend, P.L.burn, A.B. Holmes, Nature, 347, 539, 1990.
18. 徐玉娟;科學月刊,科學月刊雜誌社,台北,374期,P.126,2001年
2月號。
19. S.Wang, Y. Liu, H. Liu, G. Yu, Y. Xu, X. Zhan, F. Xi, D. Zhu, J. Phys.
Chem. B, 106, 10618, 2002.
20. D.M. Tohansson, G. Srdanov, G. Yu, M. Theander, O. Inganas, M.R.
Anderson, Macromolecules, 33, 2525, 2000.
21. D.C. Shin, Y.H. Kim, H. You, S.K. Kwon, Macromolecules, 36, 3222,
2003.
22. Y. Shirota, Y. Kuwabara, H. Inada, Appl. Phys., 65(7), 807, 1994.
23. R.H. Friend, R.W. Gymer, A.B. Holmes, J.H. Byrroughes, R.N. Marks, C.
Talianii, D.D.C. Bradley, D.A. DosSantos, J.L. Bredas, M. Loglund, W.R.
salaneck, Nature, 397, 121, 1999.
24. Y.Cao, G.M. Treacy, P. Smith, A.T. Heeger, Appl. Phys. Lett., 60(22),
2711, 1992.
25. J. Kido, K. Nagai, Y. Okamoto, T. Skotheim, Appl. Phys. Lett., 59, 2760,
1991.
26. A. Zhang, H. Von Seggen, K. Pakbag, B. Kraable, K.H.V. Schmidt, A.T.
Heeger, Synth. Met., 62, 35, 1994.
27. A.R. Broun, D.D.C. Bradley, J.H. Burroughs, R.H. Friend, N.C.
Greenham, P.L. Burn, A. Kraft, Appl. Phys. Lett., 61(23), 2793, 1992.
28. H. Antomiadis, Br. Hsieh, Ma. Abkowitz, Sa. Jenekhe, M. Stolka, Synth.
Met., 62(3), 265, 1994.
29. J. Kido, K. Hongawa, K. Okuyama, K. Naga, Appl. Phys. Lett., 64(7),
815, 1994.
30. M. Strukelj, F. Papadimitrakopoulos, T.M. Miller, L.J. Rothberg,
Science, 267(5206), 1969, 1995.
31. J. Kido, C. Ohtali, K. Hongawa, K. Okuyama, K. Nagai, Jpn. J. Appl.
Phys., 32(7A), 917, 1993.
32. 劉佳明、翁文國、陳良吉;科學月刊,科學月刊雜誌社,台北,374
期,P.115,2001年2月號。
33. S.A. Chen, C.I. Chao, Synth. Met., 79, 93, 1996.
34. M. Ranger, D. Rondeau, M. Leclerc, Macromolecules, 30, 7686, 1999.
35. W.L. Yu, J. Pei, Y. Cao, W. Huang, A.T. Heeger, Chem. Comnun., 1837,
1999.
36. 周宣良、林金福、韓于凱、王鼎章;台大工程學刊,P.111,2003年
10月。
37. C.M. Bouche, P. Berdague, H. Facoetti, P. Robin, P. Lebarny, M. Schott,
Synth. Met., 81, 191, 1996.
38. G.G. Malliar, J.C. Scott, J. Appl. Phys., 83(10), 5399, 1998.
39. H. Bassler, Polym. Adv. Technol., 9(7), 402, 1998.
40. A.B. Holmes, D.D.C. Bradley, A.R. Brown, P.L. Burn, J.H. Burroughes,
R.H. Friend, N.C. Greenham, R.W. Gymer, D.H. Halliday, R.W. Jackson,
A. Kraft, J.H.F. Martens, K. Pichler, I.D.W. Samnel, Synth. Met.,55-57,
4031, 1993.
41. C. Kittle, Introduction to solid state physics, 6th, John Wiely and son,
Singapore, 1986.
42. 李雅明,固態電子學,全華圖書公司,台灣,1997。
43. 張敏忠、楊恆隆;科學月刊,科學月刊雜誌社,台北,374期,P.118,
2001年2月號。
44. J.K. Lee, D.H. Hwang, J. Hwang, H.K. Jung, T. Zyung, S.Y. Park, Synth.
Met., 111, 489, 2000.
45. M.R. Anderssona, A.J. Heegerab, Synth. Met., 85(1-3), 1275, 1997.
46. Z. Yang, B. Hu, F.E. Karasz, J. Macromol. Sci., Pure Appl. Chem.,
A35(2), 233, 1998.
47. R.A. Wessling, J. Polym. Sci., Polym. Symp., 72, 55, 1985.
48. R.A. Wessling, R.G. Zimmerman, US Patent 3,401,152, 1968.
49. L.F. Neef, J.P. Ferraris, Macromolecules, 33(7), 2311, 2000.
50. J.N. Wilking, B.Hsieh, G.A. Arbuckle-Keil, Synth. Met., 149, 63, 2005.
51. H.G. Gilch, W.L. Wheelright, J. Polym. Sci., Part A, 4, 1337, 1996.
52. M. Hay, F.L. Klavetter, J. Am. Chem. Soc., 117(27), 7112, 1995.
53. J. Ahn, M.S. Jang, H.K. Shim, D.H. Hwang, T. Zyung, Macromolecules,
32(10), 3279, 1999.
54. L. Hontis, V. Vrindts, L. Lutsen, D. Vanderzande, J. Gelan, Polymer, 42,
5793, 2001.
55. D.D.C. Bradley, J. Phys. D: Appl. Phys., 20(11), 1389, 1987.
56. W. carruthers﹐Some modern methods of organic synthesis, 2nd, 1977.
57. S.Doi, M. Kuwabara, T. Noguchi, T. Ohnishi, Synth. Met., 55-57,
4174, 1993.
58. J. Gordon, T.J. Sheldon, D.D.C. Bradley, P.L. Burn, J. Mater. Chem.,
6(8), 1253, 1996.
59. B. Xu, J. Zhang, Y. Pan, Z. Peng, Synth. Met., 107, 47, 1999.
60. S. Wang, Y. Liu, H. Liu, G. Yu, Y. Xu, X. Zhan, F. Xi, D. Zhu, J. Phys.
Chem. B, 106, 10618, 2002.
61. H. Fang, S. Wang, S. Xiao, Y. Li, Y. Liu, L. Fan, Z. Shi, C. Du, D. Zhu,
Synth. Met., 128, 253, 2002.
62. I.N. Kang, G.J. Lee, D.H. Kim, H.K. Shim, Polymer Bulletin, 33, 89,
1994.
63. R. Tang, Z. Tang, C. Cheng, Y. Li, F. Xi, Polymer, 46, 5341, 2005.
64. R.K. McCoy, F.E. Karasz, A. Sarker, P.M. Lahti, Chem. Mater., 3,
941, 1991.
65. SJ. Chung, K.Y. Kwon, S.W. Lee, J.I. Jin, C.H. Lee, C.E. Lee, Y. Park,
Adv. Mater., 10(14), 1112, 1998.
66. N.T. Harrison, D.R. Baigent, I.D.W. Samnel, R.H. Friend, A.C.
Grimsdale, S.C. Moratti, A.B. Holmes, Physical Review B, 53(23), 15815
, 1996.
67. T. Ohnishi, S. Doi, Y. Tsuchida, T. Noguchi, IEEE, 44(8), 1253, 1997.
68. H.K. Shim, C.B. Yoon, T. Ahn, D.H. Hwang, T. Zyung, Synth. Met., 101
, 134, 1999.
69. Y.H. Kim, D.C. Shin, S.K. Keon, Polymer, 46, 4647, 2005.
70. H. Trad, A. Ltaiet, M. Majdoub, A. Bouazizi, J. Davenas, Materials
Science and Engineering C, 26, 340, 2006.
71. F. Cacialli, X.C. Li, R.H. Friend, S.C. Moratti, A.B. Holmes, Synth. Met.,
75, 161, 1995.
72. J.I. Lee, D.H. Heang, H.K. Shim, Mol. Cryst. Liq.Cryst., 247, 121, 1994.
73. B.R. Hsieh, H. Antoniadis, D.C. Bland, W.A. Feld, Adv. Mater., 7(1), 36
, 1995.
74. S.C. Lo, A.K. Sheridan, I.D.W. Samnel, P.L. Burn, J. Mater. Chem., 9,
2165, 1999.
75. H. Becker, H. Spreitzer, W. Kreuder, E. Kluge, H. Schenk, I. Parker, Y.
Cao, Adv. Mater., 12(1), 42, 2000.
76. H. Becker, H. Spreitzer, K. Ibrom, W. Kreuder, Macromolecules, 32,
4925, 1999.
77. J.P. Ruiz, J.R. Dharia, J.R. Reynolds, L.J. Buckley, Macromolecules,
, 25, 849, 1992.
78. D.M. Johansson, G. Srdanov, G. Yu, M. Theander, O. Inganas, M.R.
Anderson, Macromolecules, 33, 2525, 2000.
79. H.Y. Low, Thin Solid Film, 413, 160, 2002.
80. F. Papadimitrakopoulos, M. Yan, L.J. Rothberg, H.E. Katz, E.A.
Chandross, M.E. Galvin, Mol. Cryst. Liq. Cryst., 252, 663, 1994.
81. D.D.C. Bradley, Appl. Phys., 20, 1389, 1987.
82. D.G.J. Sutherland, J.A. Carlisle, P. ElliKer, G. Fox, T.W. Hagler, I.
Jimenez, H.W. lee, K. Pakbaz, L.J. Terminello, S.C. Williams,
F.J. Himpsel, D.K. Schuh, W.M. Tong, J.J. Jia, T.A. Callcott, D.L.
Ederev, Appl. Phys. Lett., 68, 2046, 1996.
83. A. Suzuki, J. Organomet. Chem., 576, 147, 1999.
84. S.A. Chen, H.T. Lee, Macromolecules, 26, 3254, 1993.
85. H.L. Cheng, K.F. Lin, J. Polym.Res., 6, 123, 1999.