| 研究生: |
周佳興 Chou, Chia-Hsing |
|---|---|
| 論文名稱: |
含1,2,3-三唑和1,3,4-(口咢)二唑衍生物之合成及其發光性質之研究 Studies on the Synthesis and Light-Emitting Properties of the Derivatives including 1,2,3-Triazole and 1,3,4-Oxadiazole |
| 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: | 2004 |
| 畢業學年度: | 92 |
| 語文別: | 中文 |
| 論文頁數: | 132 |
| 中文關鍵詞: | (口咢)二唑 、三唑 、有機發光二極體 |
| 外文關鍵詞: | oxadiazole, triazole, OLED |
| 相關次數: | 點閱:51 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 |
本論文之研究,主要分為兩大部分,其一為小分子的有機發光體之合成,第二部分則為光電性質的探討:
第一部分是利用雪梨酮衍生物-1,2,3,-三唑環化合物為原料,合成含1,2,3,-三唑和1,3,4-二唑為主體的小分子發光材料,並利用 MNR、EA、IR、MS…等鑑定所合成之化合物
第二部分則利用 UV-Vis、PL 及 CV 等進行光電性質之測試,在UV-Vis方面,我們合成的分子,其吸收波長在 340 nm~360 nm 左右,而其光學能量價帶在 3.05 ev~3.20 ev。在PL方面,我們發現適當的改變 R1 取代基,可以使放光波長紅移和藍移,就本論文而言,當R1為推電子基時,可使分子的放光波長紅移,反之,則藍移。改變R2之取代基,則對 UV-Vis 和 PL 影響不大,但若以吡啶取代R2之苯環,則有明顯紅移。而從CV和UV得到各分子之HOMO介於-5.80 eV ~ -5.47 eV之間而LUMO則介於-2.61 eV ~ -2.34 eV。
The thesis contents are divided into two parts; the one describes the synthesis of luminescent materials and the other is to discuss the luminescent and electric properties.
First, we synthesize the luminescent molecules containing 1, 2, 3-triazole and 1, 3, 4-oxidiazole, which are derived from sydones. Then, we identify these compounds by means of MNR、EA、IR、MS etc.
Secondly, we test the luminescent and electric properties of these compounds by UV-Vis、PL and CV. From UV/Vis spectrum, these compounds have maximum absorption wavelength in 340 nm~360 nm, and their optical band gap is in the region of 3.05 ev~3.20 ev. From PL spectrum, if we change the R1, we can make the maximum emission wavelength red shift or blue shift. When R1 is an electron-donating group,the maximum emission wavelength become red shift. On the other hand, it will be blue shift. We also find that changing the R2, only causing a little difference. However there will be apparent shift, if we replace the benzene with pyridine in R2. Finally, we utilize the UV/Vis and CV spectra to obtain the HOMO and LUMO. HOMO for these compounds are in -5.80 eV ~ -5.47 eV range and LUMO are in -2.61 eV ~ -2.34 eV range.
1.陳文章;光訊,第66 期,P.16,民86 年6 月.
2.W. Helfrich, W. G. Schneidere, Phys. Rev. Lett. 1965, 14, 229.
3.C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913.
4.林美姿;工業材料,第133 期,P.75,民87 年1 月.
5.J. H. Burrououghes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K.MacKay, R. H. Friend, P. L. Burn, A. B. Holmes, Nature, 1990, 347, 539.
6.陳金鑫, 石建民, 鄧青雲Chemistry (The Chinese Chem. Soc., Taipei) 1996, 54, 125.
7.Seizo Miyata, Hari Singh Nalwa, OrganicElectroluminescenct
Materials and Device, 1997.
8.莊坤儒;工業材料147 期,P.138,民88 年3 月.
9.M. Pope, H. P. Kalimann, P. Magnante, J. Chem. Phys. 1963, 38 , 2042.
10.M. Berggren, O. Inganas, G. Gustafsson, J. Ramusson, M. R.I. Andersson, T. Hjertberg, O. Wennerstrom, Nature, 1994, 372 , p.444
11.顏溪成, 旋轉塗佈製程研究, 行政院國家科學委員會, 1995
12.C. Adachi, T. Tsutsui, S. Saito, Appl. Phys. Lett. 1989, 55, 1489.
13.J. Kido, M. Mimoru, K. Nagai, Science, 1995, 267, 1332.
14.Y. Hamada, C. Adachi, T.Tsutsui, S. Sanito, Jpn. J. Appl. Phys. 1992, 31, 1812.
15.C. Hosokawa, Us 5, 1992, 142, 343.
16.T. Shibata, Jp 6,122,874 , 1994.
17.P. M. Borsenberger, W. Mey, A. Chowdry, Appl. Phys. 1978, 49, 273.
18.K. Natio, A. Miura, J. Phys. Chem. 1993, 97, 6240.
19.Y. Shirota, Y. Kuwabara, H. Inada, Appl. Phys. 1994, 65(7), 807.
20.C. W. Tang, S. A. VanSlyke, C. H. Chen, J. Appl. Phys. 1989, 65, 3610.
21.C. Adachi, S. Tokito, T. Tsutsui and S. Saito, Japan. J. Appl. Phys. 1988, 27, 713.
22.M. Era, C. Adachi, T. Tsutsui and S. Saito, Chem. Phys. Lett. 1991,178, 488.
23.J. Kido, M. Kohda, K. Okuyama and K. Nadai, Appl. Phys. Lett. 1992, 61, 761.
24.Y. Hamada, C. Adachi, T. Tsutsui, S. Saito, J. Chem. Soc. Jpn. 1991, 1540.
25.Y. Hamada, C. Adachi, T. Tsutsui, S. Saito, Jpn. J. Appl. Phys. 1992, 31, 1812.
26.D. O’Bradley and T. Tsutsui, J. Appl. Phys., 1997, 82, 2662.
27.K. Kawate, K.I. Ohkura, M. Yamazaki, M. Kuroda and O. Nabeta, Proc. SPIE Int. Soc. Opt. Eng., 1994, 2174, 200.
28.H. ueda, T. Kitahora, K. Furukawa and Y. Terasaka, Synth Met. 1997, 91, 257.
29.Hann , R. M. ; Hundson , C. S. J. Am. Chem. Soc. 1944, 66, 735.
30.F. R. Benson, W. L. Savell, Chem. Rev. 1950, 46, 1.
31.E. Hardegger, H. Khadem, Helv. Chim. Acta. 1947, 30, 1478
32.J. L. Riebsomer, J. Org. Chem. 1948, 13, 815.
33.C. Bennard, L.Ghosez, J. Chem. Soc. Chem. Commun. 1980, 940.
34.H. Gotthardt, L. Reiter, Chem. Ber. 1979, 112, 1635.
35.C. Wittig, F. Bangert, H. Kleiner, Ber. 1928, 61B, 1140.
36.L. A. Summers, P. F. H. Freeman, D. J. Shields, J. Chem. Soc. 1965, 3312.
37.M. Ruccia, N. Vivona, D. Spinelli, Adv. Hetercycl. Chem. 1981, 29, 141.
38.N. Vivona, G. Macaluso, C. Cusmano, V. Frenna, J. Chem. Soc. Perkin Trans 1. 1982, 165.
39.V. Frenna, N. Vivona, A. Caronia, G. Consiglio, D. Spinelli, J. Chem. Soc. Perkin Trans 1. 1984, 785.
40.V. Frenna, N. Vivona, G. Consiglio, D. Spinelli, J. Chem. Soc. Perkin Trans 2. 1984, 541.
41.M. Marky, H. Meier, A. Wunderli, H. Heimgartner, H. Schmid, H. Hansen, J. Helv. Chim. Acta. 1978, 61, 1477.
42.W. F. Kuo, I. T. Lin, S. W. Sun, M. Y. Yeh, J. Chin Chem Soc. 2001, 48, 769
43.J. Bettenhausen, P. Strohriegl, W. Brutting, H. Tokuhisa and T. Tsutsui,J. Appl. Phys. 1997, 82, 4957.
44.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.
45.S. Tokito, H. Tanaka, K. Noda, A. Okada and Y. Taga, Macromol. Symp. 1997, 125, 181.
46.C. Zhang , H. von Seggern , K. Pakbaz , B. Kraabel , H.W.Schmidt , and A. Heeger , J. Synth. Met. 1994, 62, 35
47.B.Hu , Z. Yang and F. E.Karasz , J. Appl. Phys. 1994,76, 2419
48.Z. Zhu, J. S. Moore, J. Org. Chem. 2000, 65, 116
49.J. A. Joule, Heterocycl. Chem. 1984, 35, 83
50.柯畢嘉, 林建村 , 化學. 2002, 60, 1, 85
51. M. Y.Yeh, H. J.Tien, L. Y. Huang, M. H. Chen, J. Chin. Chem. Soc. 1983, 30, 29
52. A. Eade, J. C. Earl, J. Chem. Soc. 1946, 591
53. C. J. Thoman, D. J. Voaden, I. M. Hunsberger, J. Org. Chem. 1964, 29, 2044.
54 R. E. Trifonov et al., Spectrpchimica Acta Part A. 1996, 52, 1875
55. D. C. Harris, Quantitative Chemical Analysis, W. H. Freemanand Company New York, 1995.
56. Y. Q. Liu, H. Ma, S. Liu, X. C. Li, A. K.-Y. Jen, Polymer Preprint, 1998 , 39(2) ,1089 .
57. J. L. Bredas, R. Silbey, D. S. Boudreaux, R. R. Chance, J. Am. Chem.Soc. 1983, 105, 6555.
58. D. D. C. Bradley, Synth. Met. 1993, 54, 401.