本研究合成出6個以tribenzo[b,d,f]oxepine為主架構之化合物，並分別在含氧原子的苯環對位(para-position)連接推電子基團9H-carbazole (或 9,9-dimethylacridane)及拉電子基團CN，使有機材料同時具有寬能隙和雙極性的特性，並可放出波長介於397-434 nm之藍紫色螢光。我們分別利用了UV-Vis吸收光譜、螢光分光光譜來量測化合物的光物理性質，以及光電子能譜儀量測HOMO能階亦使用了TGA、DSC來證實化合物具有高的熱裂解溫度(323−386 oC)。經由理論計算，發現這些分子的HOMO與LUMO軌域之電子雲分布趨於定域化，並與實際測得的結果具有高的HOMO、LUMO能差相符。

Six oxepine derivatives incorporsating electron excessive 9H-carbazole (or 9,9-dimethylacridane) and electron deficient cyano groups entities at the position para to oxygen of the phenyl rings containing oxygen atom have been developed successfully. The new compounds are bipolar transporting and have large HOMO/LUMO gap with purple to blue emission in the range of 397-434 nm. The photophysical property of the compounds were investigated by UV-Vis and fluorescent spectroscopic measurements, and the HOMOs were determined by photoelectron spectroscopic measurements. High thermal stability of the compounds were confirmed by TGA and DSC measurements, and the thermal decomposition temperatures are in the range of 323−386 oC. Theoretical computations indicate that the compounds have relatively localized HOMO and LUMO orbitals, which is consistent with the high HOMO/LUMO gap of the compounds.

1. 陳金鑫, 黃孝文, OLED-夢幻顯示器 Materials and Devices-OLED 材料與元件, 五南圖書, 2009.
2. 簡金雄, 陳金鑫, 二十一世紀的明星產業-有機發光二極體平面顯示器技術, 光電科技, 24, 78 (2001).
3. AN OIDA TECHNOLOGY ROADMAP, Organic Light Emitting Diodes (OLEDs) for General Illumination Update 2002.
4. 鄭榮安, 陳金鑫, 前瞻性OLED的展望──可撓曲式有機發光二極體之開發現況, 電子與材料, 11, 37(2001).
5. 郭妍希，領先業界！南韓開發出石墨烯OLED面板，可撓又不易碎。 MoneyDJ 新聞 。2017-04-11取自 http://blog.moneydj.com/news/
6. M. Pope, H. P. Kallmann, P. J. Magnante, J. Chem. Phys., 1962, 37, 2042.
7. C. W. Tang, S. A. Van Slyke, Appl. Phys. Lett., 1987, 51, 913.
8. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burns, A. B. Holme, Nature, 1990, 347, 539.
9. T. H. Huang, J. T. Lin, L. Y. Chen, Y. T. Lin, C. C. Wu, Adv. Mater., 2006, 18, 602.
10. 科普-OLED設備製造廠商及常用材料, 顯示世界。2016-05-13 選自 https://kknews.cc/zh-tw/news/rm628x.html
11. J. Salbeck, N. Yu, J. Bauer, F. WeissGrtel, H. Bestgen, Synth. Met., 1997, 91, 209.
12. Y. Shirota, K. Okumoto, H. Inada, Synth. Met., 2000, 111, 387.
13. K. R. J. Thomas, J. T. Lin, Y. T. Tao, C. W. Ko, J. Am. Chem. Soc., 2001, 123, 9404.
14. T. H. Huang, J. T. Lin, L. Y. Chen, Y. T. Lin, C. C. Wu, Adv. Mater., 2006, 18, 602.
15. Y. Tao, K. Yuan, T. Chen, P. Xu, H. Li, R. Chen, C. Zheng, L. Zhang, W. Huang, Adv. Mater., 2014, 26, 7931.
16. (a) K. Shizu, H. Tanaka, M. Uejima, T. Sato, K. Tanaka, H. Kaji, C. Adachi, J. Phys. Chem. C, 2015, 119, 1291. (b) H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature, 2012, 492, 234.
17. Principles of Molecular Photochemistry: An Introduction, University Science Books, N. J. Turro, V. Ramamurthy, J. C. Scaiano Eds., 2009.
18. Y. Kitamoto, T. Namikawa, D. Ikemizu, Y. Miyata, T. Suzuki, H.i Kita, T. Sato and S. Oi , J. Mater. Chem. C, 2015, 3, 9122.
19. (a) M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature, 1998, 395, 151. (b) D. F. O’Brien, M. A. Baldo, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett., 1999, 74, 442. (c) M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett., 1999, 75, 4. (d) C. Adachi, M. A. Baldo, S. R. Forrest, S. Lamansky, M. E. Thompson, R. C. Kwong, Appl. Phys. Lett., 2001, 78, 1622.
20. W. Liu, C. J. Zheng, K. Wang, Z. Chen, D. Y. Chen, F. Li, X. M. Ou, Y. P. Dong, X. H.Zhang, ACS Appl. Mater. Interfaces, 2015, 7, 18930.
21. T, Körzdörfer, J. L. Bredas, Acc. Chem. Res., 2014, 47, 3284
22. A. M . Brouwer, Pure Appl. Chem., 2011, 83, 2213.
23. J. Russ. Gen. Chem., 2012, 82, 206.
24. J. R. Malpass, D. A. Hemmings, A. L. Wallis, S. R. Fletcher and S. Patel, J. Chem. Soc., Perkin Trans.1, 2001, 9, 1044.
25. E. Dimitrijević, M. Cusimano, M. S. Taylor .Org. Biomol. Chem., 2014, 12, 1391.
26. (a) A. Kiyomori, J. F. Marcoux, S. L. Buchwald, Tetrahedron Lett., 1999, 40, 2657. (b) A. Klapars, J. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727. (c) M. Wolter, A. Klapars, S. L. Buchwald, Org. Lett., 2001, 3, 803. (d) D.Giang, J. F. Hartwig, J. Am. Chem. Soc., 2009, 131, 11049
27. X. Yang, H. Liu, R. Qiao, Y. Jiang, Y. Zhao, Synlett., 2010, 101.
28. I. W. Davies, J. Wu, J. F. Marcoux, M. Taylor, D. Hughes, P. J. Reider, R. J. Deeth, Tetrahedron, 2001, 57, 5061
29. (a) N. Miyaua, A. Suzuki, Chem. Commun., 1979, 19, 866; (b) A. Suzuki, J. Organomet. Chem., 1999, 576, 147. (c) D. D. Winkle and K. M. Schaab, Org. Process Res. Dev., 2001, 5, 450.
30. (a)Jones II, G., W. R. Jackson, C. Choi and W. R. Bergmark, J. Phys. Chem., 1985, 89, 294. (b) Photonic Research Systems: http://www.prsbio.com/index.html (last accessed on 15 February 2011).
31. J. B. Birks, Photophysics of Aromatic Molecules, Wiley, London, 1970.
32. G. Jones II, W. R. Jackson, C. Choi, W. R. Bergmark, J. Phys. Chem., 1985, 89, 294.
33. Herzberg, Gerhard (1971). The spectra and structures of simple free radicals. New York: Dover. ISBN 0-486-65821-X.