簡易檢索 / 詳目顯示

研究生: 鄭詠蓁
Cheng, Yung-Chen
論文名稱: 硼錯合物熱活化型延遲螢光材料合成及OLEDs元件的應用
Thermally Activated Delayed Fluorescence of Pyridyl Pyrrolide Boron(III) Complexes and Fabrication of OLEDs
指導教授: 季昀
Chi, Yun
口試委員: 蔡易州
周必泰
吳忠幟
季昀
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: 2015
畢業學年度: 103
語文別: 中文
論文頁數: 76
中文關鍵詞: 熱活化型延遲螢光有機發光二極體
相關次數: 點閱:2下載:0
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
  • 第三代利用熱活化型延遲螢光 (thermally activated delayed fluorescence, TADF) 材料的 OLED,使用低成本的有機化合物即可有高放光效率,同時突破第一代螢光材料 OLED 效率的限制及第二代磷光材料 OLED 使用貴金屬而導致高成本的問題,在近年來備受矚目。
    本論文以硼為中心原子,搭配 pyridyl pyrrolide 雙牙配位基為 electron acceptor 及兩個具有立體障礙的 carbazole 或 triphenylamine 當作 electron donor 配位基,希望利用四配位硼錯合物的四面體結構,將 HOMO 與 LUMO 形成正交狀態,降低 ΔEST 而具有 TADF 效應。利用光物理量測、電化學量測及理論計算等相關研究,探討這一系列硼錯合物的關係,並進行元件製作,得到最大外部量子效率達 13.5% 的元件結果。


    A series of novel boron complexes with electron deficient pyridyl pyrrolide and electron donating triphenylamine or phenylcarbazolyl fragment were synthesized. In this thesis, we strategically design the titled ligands such that the electron donor (HOMO) and acceptor (LUMO) moieties are spatially separated with orthogonal orientation. The slim orbital overlap between HOMO and LUMO leads to the close lying S1 and T1 states and thereby the generation of thermally activated delayed fluorescence (TADF). OLEDs using complex 2a processed by spin coating achieved an external quantum efficiency of 13.5%, demonstrating high performance boron-core based OLEDs via harvesting TADF.

    目錄 第一章、序論 1 第一節、OLED 的發展 1 第二節、OLED 元件發光原理 4 第三節、螢光、磷光與延遲螢光發光原理 9 第四節、TADF 材料發展 13 第五節、研究動機 18 第二章、實驗部分 21 第一節、藥品與分析儀器 21 藥品 21 分析儀器 21 第二節、實驗步驟 25 Acceptor ligand 合成 25 Donor Ligand 合成 26 Boron Complexes 合成 31 第三章、結果與討論 37 第一節、錯合物合成探討 37 第二節、光物理性質探討 40 第三節、電化學性質探討 48 第四節、理論計算結果與討論 51 第五節、元件製備與探討 54 第四章、結論 59 第五章、參考文獻 60 附錄 63 錯合物 2c 光物理資料 63 Boron Complexes NMR 光譜圖 64

    [1] M. Pope, P. Magnante, H. P. Kallmann, J. Chem. Phys., 1963, 38, 2042.
    [2] C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett., 1987, 51, 913-915.
    [3] 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, 1990, 347, 539-541.
    [4] S. Reineke, F. Lindner, G. Schwartz, N. Seidler, K. Walzer, B. Lussem, K. Leo, Nature, 2009, 459, 234-238.
    [5] H. Yersin, Topics in Current Chemistry. Springer, 2004, 241, 1-26.
    [6] J. B. Birks, Chem. Phys. Lett., 1970, 7, 293-295.
    [7] L. J. Rothberg, A. J. Lovinger, J. Mater. Res., 1996, 11, 3174-3187.
    [8] A. Endo, M. Ogasawara, A. Takahashi, D. Yokoyama, Y. Kato, C. Adachi, Adv. Mater., 2009, 21, 4802-4806.
    [9] (a) B. Valeur, Molecular Fluorescence:Principles and Applications, Wiley-VCH, 2002; (b) B. Wardle, Principles and Applications of Photochemistry, Wiley, 2010.
    [10] C. A. Parker, C. G. Hatchard, Trans. Faraday Soc, 1963, 59, 284.
    [11] C. A. Parker, C. G. Hatchard, Trans. Faraday Soc., 1961, 57, 1894.
    [12] (a) C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys., 2001, 90, 5048-5051; (b) M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature, 1998, 395, 151-154.
    [13] (a) T. Sajoto, P. I. Djurovich, A. B. Tamayo, J. Oxgaard, W. A. Goddard, 3rd, M. E. Thompson, J. Am. Chem. Soc., 2009, 131, 9813-9822; (b) T. Sajoto, P. I. Djurovich, A. Tamayo, M. Yousufuddin, R. Bau, M. E. Thompson, R. J. Holmes, S. R. Forrest, Inorg. Chem., 2005, 44, 7992-8003.
    [14] K. S. Yook, J. Y. Lee, Adv. Mater., 2012, 24, 3169-3190.
    [15] (a) D. Y. Kondakov, T. D. Pawlik, T. K. Hatwar, J. P. Spindler, J. Appl. Phys., 2009, 106; (b) A. Endo, M. Ogasawara, A. Takahashi, D. Yokoyama, Y. Kato, C. Adachi, Adv. Mater., 2009, 21, 4802-4806.
    [16] Y. Tao, K. Yuan, T. Chen, P. Xu, H. H. Li, R. F. Chen, C. Zheng, L. Zhang, W. Huang, Adv. Mater., 2014, 26, 7931-7958.
    [17] D. Y. Kondakov, T. D. Pawlik, T. K. Hatwar, J. P. Spindler, J. Appl. Phy., 2009, 106.
    [18] M. N. BerberanSantos, J. M. M. Garcia, J. Am. Chem. Soc., 1996, 118, 9391-9394.
    [19] (a) J. C. Deaton, S. C. Switalski, D. Y. Kondakov, R. H. Young, T. D. Pawlik, D. J. Giesen, S. B. Harkins, A. J. M. Miller, S. F. Mickenberg, J. C. Peters, J. Am. Chem. Soc., 2010, 132, 9499-9508; (b) R. Czerwieniec, J. B. Yu, H. Yersin, Inorg. Chem., 2011, 50, 8293-8301.
    [20] A. Endo, K. Sato, K. Yoshimura, T. Kai, A. Kawada, H. Miyazaki, C. Adachi, Appl. Phys. Lett., 2011, 98.
    [21] H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature, 2012, 492, 234-238.
    [22] S. P. Huang, Q. S. Zhang, Y. Shiota, T. Nakagawa, K. Kuwabara, K. Yoshizawa, C. Adachi, J. Chem. Theory Comput., 2013, 9, 3872-3877.
    [23] Q. Zhang, B. Li, S. Huang, H. Nomura, H. Tanaka, C. Adachi, Nat. Photonics, 2014, 8, 326-332.
    [24] (a) Q. G. Wu, M. Esteghamatian, N. X. Hu, Z. Popovic, G. Enright, Y. Tao, M. D'Iorio, S. N. Wang, Chem. Mater., 2000, 12, 79-83; (b) Y. Q. Li, Y. Liu, W. M. Bu, J. H. Guo, Y. Wang, Chem. Commun., 2000, 1551-1552; (c) Y. Liu, J. H. Guo, H. D. Zhang, Y. Wang, Angew. Chem. Int. Ed., 2002, 41, 182-184.
    [25] C. C. Cheng, W. S. Yu, P. T. Chou, S. M. Peng, G. H. Lee, P. C. Wu, Y. H. Song, Y. Chi, Chem. Commun., 2003, 2628-2629.
    [26] H. Y. Chen, Y. Chi, C. S. Liu, J. K. Yu, Y. M. Cheng, K. S. Chen, P. T. Chou, S. M. Peng, G. H. Lee, A. J. Carty, S. J. Yeh, C. T. Chen, Adv. Funct. Mater., 2005, 15, 567-574.
    [27] 趙雋恬, 硼錯合物的合成及熱活化型延遲螢光之探討, 國立清華大學碩士論文, 2014。
    [28] J. J. Klappa, A. E. Rich, K. McNeill, Org. Lett., 2002, 4, 435-437.
    [29] H. P. Shi, D. H. Xin, X. Q. Dong, J. X. Dai, X. H. Wu, Y. Q. Miao, L. Fang, H. Wang, M. M. F. Choi, J. Mater. Chem. C, 2014, 2, 2160-2168.
    [30] Y. D. Lin, C. T. Chien, S. Y. Lin, H. H. Chang, C. Y. Liu, T. J. Chow, J. Photochem. Photobio. A, 2011, 222, 192-202.
    [31] A. Bigot, D. Breuninger, B. Breit, Org. Lett., 2008, 10, 5321-5324.
    [32] Q. S. Zhang, J. Li, K. Shizu, S. P. Huang, S. Hirata, H. Miyazaki, C. Adachi, J. Am. Chem. Soc., 2012, 134, 14706-14709.
    [33] T. Nakagawa, S. Y. Ku, K. T. Wong, C. Adachi, Chem. Commun., 2012, 48, 9580-9582.
    [34] R. Ishimatsu, S. Matsunami, K. Shizu, C. Adachi, K. Nakano, T. Imato, J. Phys. Chem. A, 2013, 117, 5607-5612.
    [35] (a) S. J. Su, E. Gonmori, H. Sasabe, J. Kido, Adv. Mater., 2008, 20, 4189; (b) Y. Y. Lyu, J. Kwak, W. S. Jeon, Y. Byun, H. S. Lee, D. Kim, C. Lee, K. Char, Adv. Funct. Mater., 2009, 19, 420-427.
    [36] (a) Q. S. Zhang, J. Li, K. Shizu, S. P. Huang, S. Hirata, H. Miyazaki, C. Adachi, J. Am. Chem. Soc., 2012, 134, 14706-14709; (b) J. Lee, K. Shizu, H. Tanaka, H. Nomura, T. Yasuda, C. Adachi, J. Mater. Chem. C, 2013, 1, 4599-4604.
    [37] C. C. Wu, Y. T. Lin, K. T. Wong, R. T. Chen, Y. Y. Chien, Adv. Mater., 2004, 16, 61-65.

    無法下載圖示 全文公開日期 本全文未授權公開 (校內網路)
    全文公開日期 本全文未授權公開 (校外網路)

    QR CODE