小分子有機光伏打電池供體材料四併環噻吩衍生物的開發

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姓名

鄭以農(Yi-Nung Cheng) 查詢紙本館藏

畢業系所

化學學系

論文名稱

小分子有機光伏打電池供體材料四併環噻吩衍生物的開發

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摘要(中)

本論文設計並合成三個小分子有機光伏打電池的供體材料 ( DCA-T-TTAR、DCA-TH-TTAR 和 DCA-bT-TTAR )，這些化合物為對稱性的受體-供體-受體結構，以十五烷基鏈取代的 TTAR 為中心供體，再接上不同個數的噻吩，最後末端受體為氰基乙酸辛酯。利用可見光紫外光吸收光譜儀、循環伏安法、熱重分析儀分析進行物性測試，藉由光學和電化學測定推算出能階，對這一系列化何物進行徹底的研究調查，得到明確地結構與性能之間的關係。其中，DCA-bT-TTAR 以簡單的溶液旋轉塗佈製程方式初步測得效率為 2.36 %，因此，以 TTAR 為核心確實能夠開發成新的有機光伏材料。

摘要(英)

Three new tailor-made molecules ( DCA-T-TTAR, DCA-TH-TTAR, and DCA-bT-TTAR ) were strategically designed and convergently synthesized as donor materials for small-molecule organic solar cells.
These compounds possess a acceptor−donor−acceptor molecular architecture, TTAR as the central building block with pentadecyl substituted alkyl chain and octyl cyanoacetate terminal units with different linkage of thiophene.
Physical properties such as absorption spectroscopy, cyclic voltammetry and thermal gravimetric analysis were examined. Also Photophysical and electrochemical properties as well as energy levels of this series of donor molecules were thoroughly investigated, affording clear structure−property relationships.
Among them, DCA-bT-TTAR shows power conversion efficiency 2.36 % has been achieved using the simple solution spin-coating fabrication process. The results demonstrate that structure fine turning could cause significant performance difference.Thus, TTAR-related compounds are promising for developing new organic solar cells materials.

關鍵字(中)

★ 光伏打電池
★ 供體材料
★ 四併環噻吩

關鍵字(英)

論文目次

摘要 v
Abstract vi
謝誌 vii
目錄 viii
圖目錄 xii
表目錄 xiv
Scheme xv
附圖目錄 xvii
第1章緒論 1
1-1 前言 2
1-2 有機太陽能電池工作原理 3
1-3 性能參數 6
1-3-1 等效電路 6
1-3-2 J-V曲線 7
1-4 有機光伏打電池結構 10
1-4-1 雙層式異質接面（Bilayer Architecture） 11
1-4-2 體異質接面（Bulk Heterojunction Architecture） 13
1-4-3 串聯結構（Tandem organic solar cell device architecture） 16
1-5 文獻探討 20
1-6 研究動機 25
第2章實驗部分 27
2-1 化合物名稱對照 28
2-2 實驗藥品 29
2-2-1 實驗所用之化學藥品 29
2-2-2 實驗所用之溶劑除水方式 31
2-3 實驗儀器 32
2-3-1 核磁共振光譜儀（Nuclear Magnetic Resonance, NMR）； Bruker AVANCE 200 / 300 / 500 MHz 32
2-3-2 高解析質譜儀 (High Resolution Mass Spectrometer, HRMS)；JMS-700 HRMS 33
2-3-3 紫外光 / 可見光吸收光譜（Ultraviolet / Visible Spectro -Photometer）；HITACHI U-3900 型 33
2-3-4 示差熱掃描卡計（Differential Scanning Calorimeter, DSC）；NETZSCH DSC 204 F1 33
2-3-5 熱重分析儀 (Thermal Gravimetric Analyer, TGA)； Perkin Elmer TGA 7 34
2-3-6 電化學裝置 (Electrochemical Analyzer / Work- station)；HCH Instrumentent Model 621C 34
2-4 合成步驟 35
2-4-1 perbromothieno[3,2-b]thiophene (5) 之合成 35
2-4-2 3,7-Dipentadecyltetrathienoacene (9) 之合成 39
2-4-3 Octyl 3-(5-bromothiophen-2-yl)-2-cyanoacrylate (13) 之合成 43
2-4-4 Octyl 3-(5’-bromo-[2,2’-bithiophen]-5-yl)-2-cyanoacrylate (18) 之合成 46
2-4-5 Octyl 3-(5-bromo-4-hexylthiophen-2-yl)-2-cyanoacrylate (22) 之合成 50
2-4-6 dioctyl 3,3’-(5,5’-(3,7-dipentadecylthieno[2’,3’:4,5]thieno[3,2 -b]thieno[2,3-d]thiophene-2,6-diyl)bis(thiophene-5,2-diyl))bis(2-cyanoacrylate) (23) 之合成 53
2-4-7 dioctyl 3,3’-(5’,5’’’-(3,7-dipentadecylthieno[2’,3’:4,5]thieno [3,2-b]thieno[2,3-d]thiophene-2,6-diyl)bis([2,2’-bithiophene]-5’,5-diyl))bis(2-cyanoacrylate) (24) 之合成 55
2-4-8 dioctyl 3,3’-(5,5’-(3,7-dipentadecylthieno[2’,3’:4,5]thieno [3,2-b]thieno[2,3-d]thiophene-2,6-diyl)bis(4-hexylthiophene-5,2-diyl))bis(2-cyanoacrylate) (25)之合成 57
第3章結果與討論 59
3-1 合成探討 60
3-1-1 反應機構探討 61
3-1-2 2,5-Di(1,1’-pentadecanone)-3,6-dibromothieno[3,2-b]thiophene (6) 之合成探討 64
3-1-3 DCA-T-TTAR (23) 合成探討 66
3-1-4 DCA-TH-TTAR (25) 合成探討 68
3-2 UV光學性質探討 75
3-3 CV與DPV電化學性質探討 78
3-4 穩定性探討 82
3-5 結論 83
參考文獻 84
附圖 90

參考文獻

Chapin, D. M.; Fuller, C. C.; Person, G. L. J. Appl. Phys. 1954, 25, 676.
N.S.Sariciftci Polymeric photovoltaic materials Current Opinion in Solid State and Materials Science 1999, 4, 373.
Coffin, R. C.; Peet, J.; Rogers J.; Bazan , G. C. Nat. Chem. 2009, 1, 657.
Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater. 2011, 11, 44.
McEvoy, A,; Markvart, T.; Castaner, L. Practical Handbook of Photovoltaics (Second Edition), Academic Press., Switzerland, 2011.
Thompson, B. C.; Frechet, J. M. Angew. Chem. Int. Ed. Engl. 2008, 47, 58.
Mazhari, B. Sol. Energ Mat. Sol. C. 2006, 90, 1021.
Boudreault, P.-L. T.; Najari, A.; Leclerc, M. Chem. Mater. 2011, 23, 456.
Brabec, C. J.; Cravino, A.; Meissner, D.; Sariciftci, N. S.; Fromherz, T.; Rispens, M. T.; Sanchez, L. Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 374.
Arkhipov, V. I.; Heremans, P.; Bässler, H. Appl. Phys. Lett. 2003, 82, 4605.
Kietzke, T. Adv. Opto. Elec. 2007, 2007, 1.
Sariciftci, N. S.; Braun, D.; Braun, C. Zhang,; Srdanov, V. I.; Heeger, A. J.; Stucky, G.; Wudl, F. Appl. Phys. Lett. 1993, 62, 585.
Liew, Y. F.; Aziz, H,; Hu, N. X,; Chan, H. S.; Xu, G.; Popovic, Z. Appl. Phys. Lett. 2000, 77, 2650.
Chou, D.-W.; Huang, C.-J.; Wang, T.-C.; Chen, W.-R.; Meen, T.-H. J. Non-Cryst. Solids 2010, 356, 2156.
Halls J. J. M,; Pichler, K.; Friend, R. H.; Moratti, S.C.; Moratti, A. B. Appl. Phys. Lett.1996, 68, 3120.
Shao, Y.; Yang, Y. Adv. Mater. 2005, 17, 2841.
Chen, W.-B.; Xiang, H.-F.; Xu, Z.-X.; Yan, B.-P.; Roy, V. A. L.; Che, C.-M.; Lai, P.-T. Appl. Phys. Lett. 2007, 91, 191109.
Chan, M. Y.; Lai, S. L.; Fung, M. K.; Lee, C. S.; Lee, S. T. Appl. Phys. Lett. 2007, 90, 023504.
Brabec, C. J.; Durrant, J. R. MRS Bulletin 2008, 33, 670.
Yu, G.; Gao, J.; J. Hummelen, C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
Yu, G.; Srdanov, G.; J. Wang, H.; Cao, Y.; Heeger, A. J. Proc. SPIE 2001, 4108, 48.
Granstrom, M.; Petritsch, K.; Arias, A. C,; Friend, R.H. Synthetic Met. 1999, 102,957.
Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119.
Schilinsky, P.; Waldauf, C.; Brabec, C. J. Appl. Phys. Lett. 2002, 81, 3885.
Svensson, M.; Zhang, F.; Veenstra, S.C.; Verhees, W.J.H.; Hummelen, J.C.; Kroon, J.M.; Inganäs, O.; Andersson, M.R. Adv. Mater. 2003, 15, 988.
Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J. Adv. Funct. Mater. 2005, 15, 1617.
Chen, H. Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang,Y.; Yu, L.; Wu, Y.; Li, G. Nat Photonics 2009, 3, 649.
Kyaw, A. K. K.; Wang, D. H.; Gupta, V.; Leong, W. L.; Ke, L.; Bazan, G. C.; Heeger, A. J. ACS Nano 2013, 7, 4569.
Kyaw, A. K. K.; Wang, D. H.; Wynands, G.; Zhang, J.; Nguyen, T-Q.; Bazan, G. C.; Heeger, A. J. Nano Lett. Article ASAP.
Nguyen Cong, H.; Dieng, M.; Sene, C.; Chartier, P. Sol. Energy Mat Sol. C. 2000, 63, 23.
Huynh, W. U.; Dittmer, J. J.; Alivisatos, A. P. Science 2002, 295 , 2425.
Ramos, A.M.; Rispens, M.T.; van Duren, J.K.J.; Hummelen, J.C.; Janssen, R.A.J. J. Am. Chem. Soc. 2001, 123, 6714.
Krebs, F. C.; Jørgensen, M. Polym. Bull. 2003, 50. 359.
Sun, S. S. Sol. Energy Mater. Sol. C. 2003, 79, 257.
Abdulrazzaq, O. A.; Saini, V.; Bourdo, S.; Dervishi, E.; Biris, A. S. Organic Solar Cells: A Review of Materials, Limitations,and Possibilities for Improvement, Informa Press, UK, 2013.
Hiramoto, M.; Suezaki, M.; Yokoyama, M. Chem Lett., 1990, 19, 327.
Peumans, P.; Yakimov, A. Appl. Phys. Rev. 2003, 93, 3693.
Sista, S.; Park, M.-H.; Hong, Z.; Wu, Y.; Hou, J.; Kwan, W. L.; Li, G.; Yang, Y. Adv. Mater. 2010, 22, 380.
Kumar, A.; Sista, S.; Yang, Y. J Appl.Phys. 2009, 105, 094512.
Glatthaar, M.; Riede, M.; Keegan, N.; Sylvester-Hvid, K.; Zimmermann, B.; Niggemann, M.; Hinsch, A.; Gombert, A. Sol.EnergyMater.Sol.Cells 2007, 91, 390.
Yang, J.; Zhu, R.; Hong, Z.; He, Y.J.; Kumar, A.; Li, Y. F.; Yang, Y. Adv. Mater. 2011, 23, 3465.
You, J.; Dou, L.; Yoshimura, K.; Kato, T.; Ohya, K.; Moriaty, T.; Emery, K.; Chen, C.-C; Li, G.; Yang, Y. Nat. Commun. 2013, 4, 1446.
Zhang, F.; Wu, D.; Xu Y.; Feng, X. J. Mater. Chem. 2011,21, 17590.
Sakai, J.; Taima, T.; Yamanari, T.; Saito, K. Sol. Energy Mater. Sol. C. 2009, 93, 1149.
Schulze, K.; Riede, M.; Brier, E.; Reinold, E.; Bäuerle, P.; Leo, K. J. Appl. Phys. 2008, 104, 074511.
Schulze, K.; Uhrich, C.; Schüppel, R.; Leo, K.; Pfeiffer, M.; Brier, E.; Reinold, E.; Bäuerle, P. Adv. Mater. 2006, 18, 2872.
Haid, S.; Mishra, A.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Chem. Mater. 2011, 23, 4435.
Fitzner, R.; Reinold, E.; Mishra, A.; Mena-Osteritz, E.; Ziehlke, H.; Körner, C.; Leo, K.; Riede, M.; Weil, M.; Tsaryova, O.; Weiß, A.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Adv. Funct. Mater. 2011, 21, 897.
Liu, Y.; Wan, X.; Yin, B.; Zhou, J.; Long, G.; Yin, S.; Chen, Y. J. Mater. Chem. 2010, 20, 2464.
Liu, Y.; Wan, X.; Wang, F.; Zhou, J.; Long, G.; Tian, J.; You, J.; Yang, Y.; Chen, Y. Adv. Energy Mater. 2011, 1, 771.
Liu, Y.; Wan, X.; Wang, F.; Zhou, J.; Long, G.; Tian, J.; Chen, Y. Adv. Mater. 2011, 23, 5387.
Zhou, J.; Wan, X.; Liu, Y.; Long, G.; Wang, F.; Li, Z.; Zuo, Y.; Li, C.; Chen, Y. Chem. Mater. 2011, 23, 4666.
Li, Z.; He, G.; Wan, X.; Liu, Y.; Zhou, J.; Long, G.; Zuo, Y.; Zhang M.; Chen, Y. Adv. Energy Mater. 2012, 2, 74.
Jones, G.; Stanforth, S. P. Org. React. 2000, 56, 355.
Huang, H. ; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem., 2009, 74, 5599.
Slagt, V. F.; de Vries, A. H. M.; de Vries, J. G.; Kellogg, R. M. Org. Proc. Res. Develop. 2010, 14, 30.
Wang,Z. Stille Coupling. Comprehensive Organic Name Reactions and Reagents, John Wiley & Sons, Inc. 2010.
Liu, N.; Wang, Z. X. J. Org. Chem., 2011, 76, 10031.
Liu, Y.; Wan, X.; Wang, F.; Zhou, J.; Long, G.; Tian, J.; Chen, Y. Adv. Mater. 2011, 23, 5387.
Lee, M.-J.; Kang, M. S.; Shin, M.-K.; Park, J.-W.; Chung, D. S.; Park, C. E.; Kwon, S.-K.; Kim, Y.-H. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3942.
Guo, X.; Quinn, J.; Chen, Z.; Usta, H.; Zheng, Y.; Xia, Y.; Hennek, J. W.; Ortiz, R. P.; Marks, T. J.; Facchetti, A. J. Am. Chem. Soc. 2013, 135, 1986.
Wan, M.; Wu, W.; Sang, G.; Zou, Y.; Liu, Y.; Li, Y. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 4028.
Turtle, E. D.; Flippin, L. A.; Arend, M. P.; Cheng, H. U.S. Pat. Appl. Publ., 20060199836, 07 Sep 2006.
Lin, Y.; Zhan, X. Organic Solar Cells Based on Small Molecules, in Organic Optoelectronics, Wiley-VCH Verlag, Germany, 2013.

指導教授

陳銘洲(Ming-Chou Chen)

審核日期

2013-7-22

推文