| 研究生: |
吳韋菁 Wei-Ching Wu |
|---|---|
| 論文名稱: |
非結晶性紅色螢光發射團分子之合成與其光電性質之探討 Synthesis and Electrical/Optical Characterization of Amorphorous Red Fluorophores |
| 指導教授: |
楊吉水
Jye-Shane Yang 陳錦地 ChIn-Ti Chen |
| 口試委員: | |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學學系 Department of Chemistry |
| 畢業學年度: | 91 |
| 語文別: | 中文 |
| 論文頁數: | 113 |
| 中文關鍵詞: | 有機電機發光材料 、紅色螢光 |
| 外文關鍵詞: | red oled, red fluorescent |
| 相關次數: | 點閱:9 下載:0 |
| 分享至: |
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I
非結晶性紅色螢光發射團分子之合成與其光電性質之探討
摘要
本論文以maleimide 和pyrazine 為主體(結構如下圖所示),設計
合成一系列具有推、拉電子結構的螢光放射團分子,希望藉此改變分
子之螢光波長,以達到飽和紅光。再配合鄰取代位置接上芳香環,使
化合物因芳香環所造成的立體障礙,而無法共平面。這樣在固體時,
將有助於抑制分子的結晶規律排列,因此,化合物有機會是非結晶性
的。
我們藉由紫外/可見光光譜儀和螢光儀,來測量化合物之吸收、
螢光光譜,藉此得知化合物之光色。使用循環電位儀來測量化合物之
氧化還原電位,並藉此估算化合物之HOMO 和LUMO 值。藉由熱重
量分析儀和微差熱掃瞄卡計,測量化合物之有關玻璃轉移溫度、結晶
溫度和熔化溫度之結晶性與熱穩定性。
II
Synthesis and electrical/optical characterization of Amorphorous
Red Fluorophores
Abstract
Maleimide and pyrazine-based fluorophore (structure shown in blow)
with donor-acceptor substituents were designed and synthesized for
tuning fluorescence wavelength into saturated red region. We utilized the
nonplanar conformation that was generated by ortho-substituted aromatic
ring structures for enhancing the amorphous property of the fluorophores.
The absorption and fluorescence of the fluorophores were studied by
UV/Visible and fluorescence spectroscopic methods. HOMO and LUMO
energy levels were derived from cyclic voltametry (CV) data. The glass
transtition temperature(Tg), crystal temperature(Tc) and melting point(Tm)
were determined by DSC (differential scanning calorimeter) and TGA
(thermogravinetric analyzer), respectively., to estimate the amorphous
property and thermal stability of the fluorophores.
1. a) Chen, C. H.; Tang, C. W.;Shi, J.; Klubek, K. P. Macromol.
Symp.1997, 125, 49. b) Chen, C. H.; Klubek, K. P.; Shi, J. US Patent
5 908 581, 1999.
2. Chen, C. H.; Tang, C. W.; Shi, J.; Klubek, K. P. Thin Solid Films
2000, 363, 327.
3. Drexhage, K. H. Progress in Optics, edited by E. Wolf (North-
Holland, Amsterdam, 1974), Vol. 12, p. 165.
4. Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65,
3610.
5. Chen, C. H.; Tang, C. W. in Proc. 2nd Int. Symp. On the Chemistry of
Functional Dyes 1992, p. 536
6. Moylan, C. R.; Ermer, S.; Lovejoy, M. L.; McComb, I. -H.; Leung, D.
S.; Wortmann, R.; Krdmer, P.; Twieg, R. J. J. Am. Chem. Soc. 1996,
118, 12950.
7. Jung, B. -J.; Yoon, C. -B.; Shim, H. -K.; Do, L. -M.; Zyung, T. Adv.
Funct. Mater. 2001, 11, 430.
8. Woods, L. L. J. Am. Chem. Soc. 1958, 80, 1440.
9. a) Oatai, S.; Israeli, Y. J. Am. Soc. 1960, 2020. b) Boucard, V.; Ades,
D.; Siove, A.; Romero, D.; Schaer, M.; Zuppiroli, L.
Macromolecules 1999, 32, 4729.
10. Burrows, P. E.; Forrest, S. R.; Sibley, S. P.; Thompson, M. E. Appl.
Phys. Lett. 1996, 69, 2959.
11. Kwong, R. C.; Sibley, S.; Dubovoy, T.; Baldo, M.; Forrest, S. R.;
Thompson, M. E. Chem. Mater. 1999, 11, 3709.
12. Kido, J.; Hayase, H.; Hongawa, K.; Nagai, K.; Okuyama, K. Appl.
Phys. Lett. 1994, 65, 2124.
13. Mitsuya, M.; Suzuki, T.; Koyama, T.; Shirai, H.; Taniguchi, Y. Appl.
Phys. Lett. 2000, 77, 3272.
14. Toguchi, S.; Morioka, Y.; Ishikawa, H.; Oda, A.; Hasegawa, E. Synth.
Met. 2000, 111-112, 57.
15. Seguy, I.; Jolinat, P.; Destruel, P.; Farenc, J.; Mamy, R.; Bock, H.; Ip,
J.; Nguyen, T. P. J. Appl. Phys. 2001, 89, 5442.
16. Zhang, X. H.; Chen, B. J.; Lin, X. Q.; Wong, O. Y.; Lee, C. S.;
Kwong, H. L.; Lee, S. T.; Wu, S. K. Chem. Mater. 2001, 13, 1565.
17. Yu, J.; Shirota, Y. Chem. Lett. 2002, 984.
18. Tao, X. T.; Miyata, S.; Sasabe, H.; Zhang, G. J.; Wada, T.; Jiang, M. H.
Appl. Phys. Lett. 2001, 78, 279.
19. Picciolo, L. C.; Murata, H.; Kafafi, Z. H. Appl. Phys. Lett. 2001, 78,
2378.
20. Mi, B. X.; Gao, Z. Q.; Liu, M. W.; Chan, K.Y.; Kwong, H. L.; Wong,
N. B.; Lee, C. S.; Hung, L. S.; Lee, S. T. J. Mater. Chem. 2002, 12,
1307.
21. Kim, D. K.; Paik, S. H.; Kim, S. -H.; Tsutsui, T. Synth. Met. 2001, 123,
43.
22. Li, J.; Liu, D.; Hong, Z.; Wang, P.; Ma, C.; Lengyel, O.; Lee, C. -S.;
Kwong, H. -L.; Lee, S. Chem. Mater. 2003, 15, 1486.
23. Thomas, K. R.; Lin, J. T.; Tao, Y. -T.; Chuen, C. -H. Adv. Mater. 2002,
14, 822.
24. Wu, W. -C.; Yeh, H. -C.; Chan, L. -H.; Chen, C. -T. Adv. Mater. 2002,
14, 1072.
25. Lamansky, S.; Djurovich, P.; Murphy, D.; Feras, A. -R.; Lee, H. -E.;
Adachi, C.; Burrows, P. E.; Forrest, S. R.; Thompson, M. E. J. Am.
Chem. Soc. 2001, 123, 4304.
26. Duan, J. -P.; Sun, P. -P.; Cheng, C. -H. Adv. Mater. 2003, 15, 224.
27. Kijima, Y.; Asai, N.; Kishii, N.; Tamura, S. -I. IEEE Trans. Electron
Device 1997, 44, 1222.
28. Bulovic, V.; Shoustikov, A.; Baldo, M. A.; Bose, E.; Kozlov, V. G.;
Thompson, M. E.; Forrest, S. R. Chem. Phys. Lett. 1998, 287, 455.
29. Pope, M.; Kallmann, H. P.; Magnante, P. J. Chem. Phys. 1963, 38,
2042.
30. Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
31. Adachi, C.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Phys. Lett. 1991,
178, 488.
32. Klupfel, K. -W.; Sus, O.; Behmenburg, H.; Neugebauer, W. US
Patent3 180 730, 1965.
33. Brantly, T. B.; Contois, L. E.; Fox, C. J. US Patent 3 567 450, 1971.
34. Brantly, T. B.; Contois, L. E.; Fox, C. J. US Patent 3 658 521, 1972.
35. Kwong, R. C.; Nugent, M. R.; Michalski, L.; Ngo, T.; Rajan, K.; Tung,
Y. -J.; Weaver, M. S.; Zhou, T. X.; Hack, M.; Thompson, M. E.;
Forrest, S. R.; Brown, J. J. Appl. Phys. Lett. 2002, 81, 162.
36. Shirota, Y. J. Mater. Chem. 2000, 10, 1.
37. Yeh, H. -C.; Wu, W. -C.; Chen, C. -T. Chem. Commun. 2003, 404.
38. Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron. Lett. 1998, 39,
2367.
39. a) Saito, K.; Kambe, S.; Nakano, Y. Commun. Synth. 1983, 210. b)
Tamoto, N.; Adachi, C.; Nagai, K. Chem. Mater. 1997, 9, 1077. c)
Chen, J. J.; Hinkley, J. M.; Wise, D. S.; Townsend, L. B. Synth.
Commun. 1996, 26, 617.
40. Sarkar, N.; Das, K.; Neth, D. N.; Bhattacharyya, K. Langmuir 1994,
10, 326.
41. Stevens, B.; Algar, B. E. J. Phys. Chem. 1968, 72, 2582.
42. Jones Ⅱ, G.; Jackson, W. R.; Choi, C. -Y. J. Phys. Chem. 1985, 89,
294.
43. a) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi,
S. J. Am. Chem. Soc. 1996, 118, 11974. b)Yamaguchi, S.; Endo, T.
67
Uchida, M.; Izumizawa, T.; Furukawa, K.; Tamao, K. Chem.-Eur. J.
2000, 6, 1683. c) Uchida, M.; Izumizawa, T.; Nakano, T.; Yamaguchi,
S.; Tamao, K.; Furukawa, K.; Tamao, K. Chem. Mater. 2001, 13, 2680.
d) Murata, H.; Malliaras, G. G.; Uchida, M.; Shen, Y.; Kafafi, Z. H.
Chem. Phys. Lett. 2001, 339, 161.