| 研究生: |
李盈儒 Li, Ing-Ju |
|---|---|
| 論文名稱: |
9-取代-3-(5-芳香基-[1,3,4] oxadiazole -2-基)-9氫-carbazole之合成及發光性質研究 Studies on the Synthesis and Light-Emitting Properties of 9-Substituted-3-(5-aryl-[1,3,4]oxadiazol-2-yl)-9H-carbazole |
| 指導教授: |
葉茂榮
Yeh, Mou-Yung |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2003 |
| 畢業學年度: | 91 |
| 語文別: | 中文 |
| 論文頁數: | 110 |
| 中文關鍵詞: | �Q二�t環 、�w�t |
| 外文關鍵詞: | oxadiazole, carbazole |
| 相關次數: | 點閱:158 下載:2 |
| 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 |
本論文係利用�w�t(carbazole)為原料,以KMnO4當環化試劑製備發光小分子材料,並經由NMR、EA、IR、DSC、TGA、UV-VIS、CV、PL光譜數據及EL測試,以探討含�w�t系列以及�w�t含�G�H化合物之結構、物性及光電性質影響。
在熱穩定性質方面,所合成化合物均具有良好的的熱裂解溫度(Td>306℃)。在玻璃轉化溫度(glass transition temperature,Tg)方面,化合物有Tg點,而且Tg點低,屬於不理想的。
由PL結果中,發現取代基的改變,歸納�`�t化合物氮上取代基為長碳鏈有影響,而氮上取代基為�`基沒有影響放光的波長。
元件製作方面,以真空蒸鍍的方式成膜而製成元件。測試時,由於發光時間過短,無法得到EL圖譜為本論文之遺憾。歸納原因,由於電洞傳輸速度比電子傳輸速度快太多。因此加入一材質使電洞傳輸速度降低,或著改變元件設計。
In this thesis the luminescent organic material was synthesized using carbazole as a starting material and KMnO4 as a cyclization reagent. The structure, physical and electroluminiecent properties for the obtained products including carbazole series and their indole derivatives were studied by the analysis of NMR elemental analysis IR, DSC,TGA,UV-VIS,CV,PL spectrum and EL test.
For the thermal stability , all synthesized compounds had good thermal decomposition temperatures ,but low glass transition temperatures.
The result for PL spectrum analysis indicated that substituted groups for the compounds with a long chain on N position effect the PL spectrum but with benzyl group on N position not.
The EL device was fabricated by depositing as a film in vacumn and tested to emit too instantly to gain the EL spectrum . This was attributed to the larger velocity for hole-transport than electron-transport.
This can be modified by adding the material which can lower the velocity of hole-transport or enhancing the thickness of the deposited film for emitting layer.
1. M. Pope , H. P. Kallman and P. Mangnante, J. Chem. Phys. 1963, 38; 2042.
2. C. W. Tang and S. A. VanSlyke, Appl. Phys. Lett. 1987, 51; 913.
3. C. W. Tang, S. A. VanSlyke and C. H. Chen, J. Appl. Phys. 1989, 65; 3610.
4. C. Adachi, S. Tokito, T. Tsutsui and S. Saito, Japan. J. Appl. Phys. 1988, 27; L713.
5. M. Era, C. Adachi, T. Tsutsui and S. Saito, Chem. Phys. Lett. 1991, 178; 488.
6. J. Kido, M. Kohda, K. Okuyama and K. Nadai, Appl. Phys. Lett. 1992, 61; 761.
7. J. Kido, M. Kimura, K. Nagai, Science, 1995, 267; 1332.
8. K. –W. Klupfel, O. Sus, H. Behmenburg and W. Neugebauer, Us 3, 1965, 180; 730.
9. T. B. Brantly, L. E. Contois and C. J. Fox, Us 3, 1971, 567; 450.
10. T. B. Brantly, L. E. Contois and C. J. Fox, Us 3, 1972, 658; 520.
11. Y. Hamada, C. Adachi, T.Tsutsui and S. Sanito, Jpn. J. Appl. Phys. 1992, 31; 1812.
12. J. Kido, Jpn. J. Appl. Phys. 1993, part2, 32(7A); L917.
13. C. Hosokawa, Us 5, 1992, 142; 343.
14. T. Shibata, Jp 6,122,874 , 1994.
15. M. Tashiro, S. Mataga, K. Takahashi, S. Saito, T. Tsutsui, C. Adachi, Y. Sato, S. Maeda, US 5,059,863 1991
16. T. Kudo, Ep 499,011 1991
17. J. H. Burroughs, D. D. C. Bradley, A. R. Brown, R. N. Markes, K. Markay, R. H. Friend, P. L. Burns and A. B. Holmes, Nature, 1990, 347; 539.
18. D. Braun, A. J. Heeger, Appl. Phys. Lett., 1991, 58;1982.
19. F. Cacialli, X.C. Li, R. H. Friend, S. C. Moratti, A. B. Holmes, Synth. Met., 1995, 75; 161.
20. S.A., Chen, Y.Z., Lee, International Conference on Organic Electrolumincescent Materials, 1996, Sep.;14-17.
21. S.J. Chung, K.Y. Kwon, S.W. Lee, J. I. Jin, C. H. Lee, Y. Park, Adv. Mater., 1998, 10; 1112.
22. Z. Bao, J. A. Roger, A. Dodabalapur, A. J. Lovinger, H. E. Katz, V. R. Raju, Z. Peng, M. E. Galvin, Opt. Mater., 1999, 12; 177.
23. H. Meng, W.L. Yu, W. Huang, Macromolecules, 1999, 32; 8841.
24. M. Tashiro, S. Mataga, K. Takahashi, S. Saito, T. Tsutsui, C. Adachi, Y. Sato, S. Maeda, US 5,059,863 1991
25. T. Kudo, Ep 499,011 1991
第五章、參考文獻
1. C. Zhang , H. von Seggern , K. Pakbaz , B. Kraabel , H.W.Schmidt , and A. Heeger , J. Synth. Met. , 1994 ,62 , 35
2. B.Hu , Z. Yang and F. E.Karasz , J. Appl. Phys. , 1994 ,76 , 2419
3. Z. Zhu ; J. S. Moore. J. Org. Chem. , 2000 , 65 , 116
4. J. A. Joule , Heterocycl. Chem. , 1984 , 35 , 83
5. 柯畢嘉, 林建村 , 化學, 2002. , 60 , 1 , 85
6. C. Adachi, T. Tsutsui and S. Saito, Appl. Phys. Lett. 1989, 55, 1489
7. Y. Hamada, C. Adachi, T. Tsusui and S. Saito, Jpn. J. Appl.Phys. 1991, 1540.
8. Y. Hamada, C. Adachi, T. Tsusui and S. Saito, Jpn. J.Appl. Phys. 1992, 31, 1812.
9. D. O’Bradley and T. Tsutsui, J. Appl. Phys. 1997, 82, 2662.
10. K. Kawate, K. –I. Ohkura, M. Yamazaki, M. Kuroda and O. Nabeta, Proc.SPIE Int. Soc. Opt. Eng. 1994, 2174, 200.
11. H. Ueda, T. Kitahora, K. Furukawa and Y. Terasaka, Synth. Met. 1997, 91,257.
12. J. Bettenhausen, P. Strohriegl, W. Brutting, H. Tokuhisa and T. Tsutsui,J. Appl. Phys. 1997, 82, 4957.
13. Y. Shirota, Y. Kuwabara, D. Okuda, R. Okuda, H. Ogawa, H. Inada, T. Wakimoto, H. Nakada, Y. Yonemoto, S. Kawami and K. Imai, J. Luminesc. 1997, 72-74, 985.
14. S. Tokito, H. Tanaka, K. Noda, A. Okada and Y. Taga, Macromol. Symp. 1997,125, 181.
15. O. A. Salman and H. G. Drickamer , J.Chem. Phys. , 1982 , 77 , 3329
16. K. D. Ashby , K. Das and J. W. Petrich , Anal. Chem. , 1997 , 69 , 1925
17. P. R. Callis , J. Chem. Phys. , 1991 , 95 , 6 , 4230
18. L. S. Andres and B. O. Roos , J. Am. Chem. Soc. , 1996 , 118 , 185
19. R. N. Goyal , N. Kumar and N. K. Singhal , Bioelectro. and
Bioenerg. , 1998 , 45 , 47
20. M. Y. Yeh, J. H. Tien , Y. L. Haung , H. M. Chen , J. Chin. Chem. Soc., 1983 , 30, 29
21. P. S. N. Reddy , P. P. Reddy , Indian J. Chem. Sect. B , 1987 , 26B , 890