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研究生: 許勝杰
Shen-Chieh Hsu
論文名稱: 利用銅觸媒進行具成本效益之并三噻吩合成研究及其在鈣鈦礦太陽能電池的應用
Dithienothiophenes (DTT) : Cost-Effective Synthesis and Application for Perovskite Solar Cells through Copper-Catalysis
指導教授: 劉青原
口試委員:
學位類別: 碩士
Master
系所名稱: 工學院 - 化學工程與材料工程學系
Department of Chemical & Materials Engineering
論文出版年: 2019
畢業學年度: 107
語文別: 中文
論文頁數: 115
中文關鍵詞: 并三噻吩鈣鈦礦太陽能電池銅觸媒
相關次數: 點閱:10下載:0
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  • 隨著關於能源的議題越來越受到重視,近年來太陽能電池的研究熱度也跟著水漲船高,其中,有機化合物分子更是占有舉足輕重的地位。
    并三噻吩(dithieno[3,2-b:2’,3’-d]thiophene, DTT)作為高度平面性的有機小分子,在有機太陽能電池(organic photovoltaic, OPV)、有機場效電晶體(organic field-effect transistor, OFET)、有機發光二極體(organic light-emitting diode, OLED)及染料敏化太陽能電池 (dye-sensitized solar cell, DSSC)等領域之應用不勝枚舉,同時亦具有相當不錯的光電性質表現,長久以來一直受到科學家們的青睞。
    然而,隨著新型態太陽能電池的推陳出新,鈣鈦礦太陽能電池(Perovskite Solar Cell, PSC)儼然成為新的趨勢,而截至目前為止,將并三噻吩應用於此領域之研究尚且不多,因此在本次研究中,我們開發出以并三噻吩為中心結構之分子,並將其應用於鈣鈦礦太陽能電池中。
    而在另一方面,并三噻吩合成成本極高,這對於太陽能電池之應用極為不利,因此本研究提出一種新的合成方式,以降低其成本。


    As importance of the energy issue, recently the research of the solar cell became more and more attracted, and the organic molecule which can be applied in it played an impotant role.
    Dithieno[3,2-b:2’,3’-d]thiophene (DTT) as a high planar molecule was widely used in many kinds of solar cells such as organic photovoltaic (OPV), organic field-effect transistor (OFET), organic light-emitting diode (OLED) and dye-sensitized solar cell (DSSC), which has attracted our attention for a long time.
    However, among the development of the new type solar cell, Perovskite Solar Cells (PSC) became a new trend. In addition, there was only few application of DTT in perovskite solar cells. So in this research we designed a new DTT-core structure as a hole-transporting material (HTM) and applied in PSC device.
    On the other hand, the traditional synthetic route of DTT was complex, difficult to purify, and needed both high-cost and toxic reagents, so we developed a new method which is step-economical, environmental-friendly and low-cost.

    摘要 i 英文摘要 ii 謝誌 iii 圖目錄 vi 表目錄 viii 表目錄II x 化合物對照表 xi 一、緒論 - 1 - 1-1緣起 - 1 - 1-2并三噻吩分子特性與其應用 - 3 - 1-3鈣鈦礦太陽能電池之開端以及發展歷史 - 10 - 1-4鈣鈦礦太陽能電池之工作原理 - 15 - 二、研究動機 - 20 - 三、結果與討論 - 25 - 3-1以銅催化反應改良并三噻吩之合成方法 - 25 - 3-1-1并三噻吩合成條件最適化 - 28 - 3-2藉由銅催化劑及直接碳氫鍵芳香環化反應來製備以并三噻吩為核心結構之D-π-A型電洞傳輸材料 - 37 - 3-2-1 D-π-A型電洞傳輸材料之合成 - 39 - 3-2-2反應機制探討 - 44 - 3-3并三噻吩核心之小分子電洞傳輸材料之性質探討 - 47 - 3-3-1光學性質探討 - 47 - 3-3-2電化學性質量測及能階計算 - 50 - 3-3-3熱性質量測及分析 - 54 - 3-3-4鈣鈦礦太陽能電池之元件表現 - 59 - 四、結論與展望 - 70 - 五、實驗部分 - 71 - 5-1藥品溶劑與儀器設備 - 71 - 5-2鈣鈦礦太陽能電池元件製程 - 74 - 5-3并三噻吩系列及電洞傳輸材料SCH-A, SCH-A01, SCH-B, SCH-B01之合成與鑑定 - 76 - 六、核磁共振圖譜 - 85 - 七、參考文獻 - 90 -

    [1] Fang, X.-S.; Bando, Y.; Gautam, U. K.; Ye, C.-H.; Golberg, D. J. Mater. Chem. 2008, 18, 509-522.
    [2] Kim, D.; Lee, N.; Park, Y. I.; Hyeon, T. Bioconjugate Chem.2017, 28, 115-123.
    [3] Gao, N.; Fang, X.-S. Chem. Rev. 2015, 115, 8294-8343.
    [4] Huang, L.; Hu, X.; Chi, L. Langmuir 2015, 31, 9748-9761.
    [5] Melville, O. A.; Lessard, B. H.; Bender, T. P. ACS Appl. Mater. Interfaces 2015, 7, 13105-13118.
    [6] Wang, C.-L.; Dong H.-L.; Jiang, L.; Hu, W.-P. Chem. Soc. Rev. 2018, 47, 422-500.
    [7] Fujimoto, R.; Yamashita, Y.; Kumagai, S.; Tsurumi, J.; Hinderhofer, A.; Broch, K.; Schreiber, F.; Watanabe, S.; Takeya, J. J. Mater. Chem. 2017, 5, 12023-12030.
    [8] Warczak, M.; Gryszel, M.; Jakešová, M.; Đerek, V.; Głowacki, E. D. Chem. Commun., 2018, 54, 1960-1963.
    [9] Jung, J.-W.; Liu, F.; Russell, T. P.; Jo, W.-H. Energy Environ. Sci., 2012, 5, 6857-6861.
    [10] Li, Z.; Malenfant, P.; Tao, Y.; Ding, J.-F. Macromol. Chem. Phys. 2012, 214, 447-452.
    [11] Guan, L.; Yin, X.; Zhao, D.; Wang, C.; An, Q.; Yu, J.; Shrestha, N.; Grice, C. R.; Awni, R. A.; Yu, Y.; Song, Z.; Zhou, J.; Meng, W.; Zhang, F.; Ellingson, R. J.; Wang, J.; Tang, W.; Yan, Y. J. Mater. Chem. A 2017, 5, 23319-23327.
    [12] Shahid, M.; Ashraf, R. S.; Huang, Z.-G.; Kronemeijer, A. J.; McCarthy-Ward, T.; McCulloch, I.; Durrant, J. R.; Sirringhaus, H.; Heeney, M. J. Mater. Chem., 2012, 22, 12817-12823.
    [13] Park, J. K.; Walker, B.; Seo, J.-H. ACS Appl. Mater. Interfaces 2013, 5, 4575-4580.
    [14] Mazzeo, M.; Vitale, V.; Sala, F. D.; Anni, M.; Barbarella, G.; Favaretto, L.; Sotgiu, G.; Cingolani, R.; Gigli, G. Adv. Mater. 2005, 17, 34-39.
    [15] Osken, I.; Gundogan, A. S.; Tekin, E.; Eroglu, M. S.; Ozturk, T. Macromolecules 2013, 46, 9202-9210.
    [16] Tian, H.; Yang, X.; Chen, R.-K.; Zhang, R.; Hagfeldt, A.; Sun, L.-C. J. Phys. Chem. C 2008, 112, 11023-11033.
    [17] Kwon, T.-H.; Armel, V.; Nattestad, A.; MacFarlane, D. R.; Bach, U.; Lind, S. J.; Gordon, K. C.; Tang, W.-H.; Jones, D. J.; Holmes, A. B. J. Org. Chem .2011, 76, 4088-4093.
    [18] Liu, X.-P.; Kong, F.-T.; Guo, F.-L.; Cheng, T.; Chen, W.-C.; Yu, T.; Chen, J.; Tan, Z.; Dai, S.-Y. Dyes and Pigments 2017, 139, 129-135.
    [19] O'Regan, B.; Grӓtzel, M. Nature 1991, 353, 737-740.
    [20] Bach, U.; Lupo, D.; Comte, P.; Moser, J. E.; Weissörtel, F.; Salbeck, J.; Spreitzer, H.; Grӓtzel, M. Nature 1998, 395, 583-585.
    [21] Kim, H.-S.; Lee, C.-R.; Im, J.-H.; Lee, K.-B.; Moehl, T.; Marchioro, A.; Moon, S.-J.; Humphry-Baker, R.; Yum, J.-H.; Moser, J. E.; Grӓtzel, M.; Park, N.-G. Sci. Rep. 2012, 2, 591-597.
    [22] Salbeck, J.; Yu, N.; Bauer, J.; Weissörtel, F.; Bestgen, H. Synth. Met. 1997, 91, 209-215.
    [23] Poplavskyy, D.; Nelson, J. J. Appl. Phys. 2003, 93, 341-346.
    [24] Kron, G.; Egerter, T.; Werner, J. H.; Rau, U. J. Phys. Chem. B 2003, 107, 3556-3564.
    [25] (a) Saragi, T. P. I.; Spehr, T.; Siebert, A.; Fuhrmann-Lieker, T.; Salbeck, J. Chem. Rev. 2007, 107, 1011-1065; (b) Jeon, N. J.; Lee, H. G.; Kim, Y. C.; Seo, J.; Noh, J. H.; Lee, J.; Seok, S. I. J. Am. Chem. Soc. 2014, 136, 7837-7840.
    [26] https://www.nrel.gov/pv/assets/images/thumb-best-research-cell-efficiencies-190416.png
    [27] 國立中央大學化材所,2018年蔣佳樺之碩士論文
    [28] 國立中央大學化材所,2018年林伯翰之博士論文
    [29] Bi, D.; Mishra, A.; Gao, P.; Franckevicius, M.; Steck, C.; Zakeeruddin, S. M.; Nazeeruddin, M. K.; Bauerle, P.; Gratzel, M.; Hagfeldt, A. ChemSusChem 2016, 9, 433-438.
    [30] Leriche, P.; Raimundo, J.-M.; Turbiez, M.; Monroche, V.; Allain, M.; Sauvage, F.-X.; Roncali, J.; Frère, P.; Skabara, P. J. J. Mater. Chem. 2003, 13, 1324-1332.
    [31] Lim, H. C.; Kim, J.-J.; Jang, J.; Hong, J.-I. New J. Chem. 2018, 42, 11458-11464.
    [32] Oechsle, P.; Paradies, J. Org. Lett.2014, 16, 4086-4089
    [33] Song, Y.‐T.; Lin, P.‐H.; Liu, C.‐Y. Adv. Synth. Catal. 2014, 356, 3761-3768.
    [34] Harschneck, T. H.; Zhou, N.-J.; Manley, E. F.; Lou, S. J.; Yu, X.-G.; Butler M. R.; Timalsina, A.; Turrisi, R.; Ratner, M. A.; Chen, L. X.; Chang, R. P. H.; Facchetti, A.; and Marks, T. J. Chem. Commun. 2014, 50, 4099-4101.
    [35] Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185-15192.
    [36] Chang, S.-Y.; Lin, P.-H.; Liu, C.-Y. RSC Adv. 2014, 4, 35868-35878.
    [37] Zhao, P.; Yin, H.; Gao, H.-X.; Xi, C.-J. J. Org. Chem. 2013, 78, 5001-5006
    [38] Heredia, A. A.; Soria-Castro, S. M.; Bouchet, L. M.; Oksdath-Mansilla, G.; Barrionuevo, C. A.; Caminos, D. A.; Bisogno, F. R.; Argüelloa, J. E.; Peñéñory, A. B. Org. Biomol. Chem 2014, 12, 6516-6526
    [39] Zhao, D.-B.; Wang, W.-H.; Yang, F.; Lan, J.-B.; Yang, L.; Gao, G.; You, J.-S. Angew. Chem. Int. Ed. 2009, 48, 3296-3300.
    [40] 國立中央大學化材所,2017年黃泂淮之碩士論文
    [41] Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074-1086.
    [42] Xie, Z.-Y.; Zhu, X.-J.; Guan, Y.-F.; Zhu, D.-R.; Hu, H.-W.; Lin, C.; Pan, Y.; Jiang, J.-L.; Wang, L.-Y. Org. Biomol. Chem. 2013, 11, 1390-1398
    [43] Zimmermann, I.; Urieta‐Mora, J.; Gratia, P.; Aragó, J.; Grancini, G.; Molina‐Ontoria, A.; Ortí, E.; Martín, N.; Nazeeruddin, M. K. Adv. Energy Mater. 2017, 7, 1601674-1601681.
    [44] Schölin, R.; Karlsson, M. H.; Eriksson, S. K.; Siegbahn, H.; Johansson, E. M. J.; Rensmo, H. J. Phys. Chem. C 2012, 116, 26300-26305.
    [45] Juarez-Perez, E. J.; Leyden, M. R.; Wang, S.; Ono, L. K.; Hawash, Z.; Qi, Y. Chem. Mater. 2016, 28, 5702-5709.
    [46] Malzkuhn, S.; Guo, X.-W.; Häussinger, D.; Wenger, O. S. J. Phys. Chem. A 2019, 123, 96-102
    [47] Sasada, T.; Anryu, M.; Saito, T.; Okamura, R. (Sumitomo Co., JP). Light emitting element and composition used in said light emitting element. WO Patent 2,016,170,671, October 27, 2016.

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