| 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 |
| 分享至: |
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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.
[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.