雙噻吩併吡咯併噻吩衍生物之有機光電材料開發

以作者查詢圖書館館藏

、以作者查詢臺灣博碩士

、以作者查詢全國書目

、勘誤回報

、線上人數：31

、訪客IP：3.128.199.242

姓名

蔡宜均(I-Chun Tsai) 查詢紙本館藏

畢業系所

化學學系

論文名稱

雙噻吩併吡咯併噻吩衍生物之有機光電材料開發
(Development of Dithienopyrrolothiophene(DTPT) of Organic Optoelectronic Applications.)

相關論文

★ Cycloiptycene分子之合成與自組裝行為之研究	★ 含二噻吩蒽[3,2-b:2′,3′-d]噻吩單元之敏化染料太陽能電池
★ 以有機磷酸修飾電極表面功函數及對有機發光元件效率影響研究	★ 有機薄膜電晶體材料三併環及四併環噻吩衍生物之開發
★ 具交聯結構之磺酸化聚馬來醯亞胺高分子質子傳導膜之開發與製備	★ 有機薄膜電晶體材料苯三併環噻吩及苯四併環噻吩衍生物之開發
★ 有機薄膜電晶體高分子材料併環噻吩系列之開發	★ 有機薄膜電晶體材料及可溶性有機薄膜電晶體材料衍生物之開發
★ 有機薄膜電晶體材料三併環及四併環噻吩衍生物之開發	★ 具交聯結構之苯乙烯-馬來醯亞胺接枝型高分子質子傳導膜之開發與製備
★ 有機薄膜電晶體材料苯三併環噻吩及可溶性聯噻吩衍生物之開發	★ 可溶性有機薄膜電晶體材料三併環及四併環噻吩衍生物之開發
★ 含benzotriazole 之D-π-A 共軛形光敏染料及其染料太陽能電池	★ 有機薄膜電晶材料苯併環噻吩和可溶性硫醚噻吩衍生物之開發
★ 具咪唑鹽團聯高分子之陰離子傳導膜的開發與製備	★ 可溶性有機薄膜電晶體材料三併環及四併環噻吩衍生物之開發

檔案

[Endnote RIS 格式]

[Bibtex 格式]

[相關文章]

[文章引用]

[完整記錄]

[館藏目錄]

至系統瀏覽論文 (2028-6-28以後開放)

摘要(中)

本論文研究主要分為有機光伏打電池(Organic Photovoltaic, OPVs)和鈣鈦礦電池(Perovskites Solar Cells, HTLs)材料之開發。
本研究主要延續之前開發出的雙噻吩併吡咯併噻吩 (DTPT)核心，再接上碳鏈 b-C20H41 以增加溶解度，之後外接五種不同拉電子單元，開發出 INF-DTPT-20 (1)、INBr-DTPT-20 (2)、DCV-DTPT-20 (3) 三種有機光伏打電池材料。此外，以DTPT為核心，外接Triarylamine-Functionalized Imidazolyl-Capped group 作為推電子基團，開發出DTPT-Im4D-20 (4) 應用於鈣鈦礦太陽能電池電洞傳輸層材料。另外，INF-DTPT-20 與DCV-DTPT-20正進行熱電性能的測試，未來可望成為有機熱電材料(Organic thermoelectric materials , OTMs)。
這些新材料的電化學及光學性能 (HOMO/LUMO 與 Eg) 已藉由 DPV 及 UV-Vis 測定，材料之熱穩定性已透過 TGA 及 DSC 檢測，這些新開發的有機光電材料正進行其相關之元件測試。

摘要(英)

A series of new organic optoelectronic materials were synthesized and characterized for applications in organic photovoltaic cells (OPVs), and perovskite solar cells (PSCs).
This study involves the development of a previously designed fused five-ring dithienopyrrolothiophene (DTPT) core and utilizing the longer alkyl chains (b-C20H41) to increase the solution processability. Wherein, the DTPT core was end-capped with various electron-withdrawing groups, such as dicyanomethylene indanone (IN), and its chloro- (INCl), bromo- (INBr), fluoro- (INF) derivatives and dicyanovinyl (DCV), via Knoevenagel condensation, yielding three new compounds, namely INF-DTPT-20 (1), INBr-DTPT-20 (2), and DCV-DTPT-20 (3) for OPVs or PSCs. In addition, DTPT was used as the core to develop DTPT-Im-4D (4) by attaching a Triarylamine-Functionalized Imidazolyl-Capped group as an electron-donating unit, which can be applied as a hole-transporting material for the PSCs. Furthermore, compounds 1 and 3 are under thermal conductivity testing and are expected to become organic thermoelectric materials (OTMs) in the future.
The optical and electrochemical properties of these newly developed compounds were characterized by UV-vis spectroscopy and DPV. Chemical structures were characterized by 1H NMR, 13C NMR, and mass spectrometry. Thermal properties were investigated by DSC and TGA. At present, optoelectronic devices based on these new organic semiconductors and non-fullerene acceptors are under optimization.

關鍵字(中)

★ 雙噻吩併吡咯併噻吩

關鍵字(英)

★ Dithienopyrrolothiophene (DTPT)

論文目次

摘要 IV
ABSTRACT V
謝誌 VII
目錄 VIII
LIST OF FIGURES XII

LIST OF SCHEMES XIV
LIST OF TABLES XVI
附錄目錄 XVII
第一章緒論 1
1-1 有機太陽能電池之前言 2
1-2 有機太陽能電池的發展 3
1-2-1 矽晶太陽能電池 6
1-2-2 無機化合物半導體太陽能電池 6
1-2-3 有機太陽能電池 7
1-3 有機光伏打電池之元件結構 8
1-3-1 雙層式異質接面 (Bilayer heterojunction) 9
1-3-2 總體異質接面 (Bulk heterojunction, BHJ) 9
1-3-3 串聯結構 10
1-4 有機光伏打電池之運作原理 10
1-4-1 光激發 (Optical absorption) 12
1-4-2 激子擴散與分離 (Exciton diffusion and dissociation) 12
1-4-3 電荷傳輸 (Charge transfer) 12
1-4-4 電荷收集 (Charge collection) 13
1-5 有機光伏打電池參數介紹 13
1-5-1 J-V 曲線 14
1-5-2 短路電流 (Short circuit current, JSC) 15
1-5-3 開路電壓 (Open circuit voltage, VOC) 15
1-5-4 外部量子效率 (Eternal quantum efficiency, EQE) 16
1-5-5 填充因子 (Fill factor, FF) 16
1-5-6 能量轉換效率 (Power conversion efficiency, PCE) 17
1-6 富勒烯與非富勒烯受體 17
1-6-1非富勒烯稠環電子受體 19
1-7 有機光伏打電池材料 20
1-7-1 P-type 有機光伏打材料 20
1-7-2 N-type 有機光伏打材料 23
1-8 有機薄膜的製備方式 30
1-8-1 氣相沉積 30
1-8-2 液相沉積 31
1-9 鈣鈦礦太陽能電池簡介 34
1-9-1 基本構造 35
1-9-2 工作原理 37
1-9-3 添加劑 (Additives) 37
1-9-4 電洞傳輸材料 HTM (Hole Transporting Material) 40
1-10 研究動機與目的 43
1-10-1 有機光伏打電池材料 43
1-10-2 鈣鈦礦電池電動傳輸層材料 46
第二章實驗部份 48
2-1 化合物名稱對照表 49
2-2 實驗藥品 50
2-2-1 實驗所用之化學藥品 50
2-2-2 實驗所用之溶劑除水方式 53
2-3 實驗儀器 53
2-3-1 核磁共振光譜儀 (Nuclear Magnetic Resonance, NMR)；Bruker AVANCE 300 / 500 MHz 53
2-3-2 高解析質譜儀 (High Resolution Mass Spectrometer, HRMS)；ATS-00670, Bruker, New ultrafleXtremeTM, Bremen, D.E. 54
2-3-3 紫外光 / 可見光吸收光譜 (Ultraviolet / Visible Spectro -Photometer)；HITACHI U-3900 、U-4100型 55
2-3-4 示差熱掃描卡計 (Differential Scanning Calorimeter, DSC)；METTLER TOLEDO DSC 1 / DSC 3 55
2-3-5 熱重分析儀 (Thermal Gravimetric Analyer, TGA)； TGA 55 55
2-3-6 電化學裝置 (Electrochemical Analyzer / Work- station)；HCH Instrumentent Model 621C 56
2-4 合成步驟 56
2-4-1 2-Octyldodecan-1-amine (7) 之合成 56
2-4-2 2-(5,6-Dibromo-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (10, INBr) 之合成 58
2-4-3 2-(5,6-Difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (15, INF) 之合成 60
2-4-4 3,3′,3′′,4′-Tetrabromo-2,2′:5′,2′′-terthiophene (16) 之合成 64
2-4-5 diCHO-DTPT-b20 (18) 之合成 65
2-4-6 INF-DTPT-b20 (1) 之合成 67
2-4-7 INBr-DTPT-b20 (2) 之合成 68
2-4-8 DCV-DTPT-b20 (3) 之合成 69
2-4-9 1,2-bis(4′-(bis(4-methoxyphenyl)amino)-[1,1′-biphenyl]-4-yl)ethane-1,2-dione 之合成 (21) 之合成 70
2-4-8 DTPT-Im4D-b20 (4) 之合成 74
第三章結果與討論 75
3-1 有機半導體材料之光學性質探討 76
3-1-1 有機光伏打電池電池材料 (OPV) 76
3-1-2 鈣鈦礦電池電動傳輸層材料 (PSCs HTM) 78
3-2 有機半導體材料之電化學性質探討 79
3-2-1 有機光伏打電池電池材料 (OPV) 80
3-2-2 鈣鈦礦電池電動傳輸層材料 (PSCs HTM) 81
3-3 有機半導體材料之熱穩定性分析 83
3-3-1 有機光伏打電池電池材料 (OPV) 83
3-3-2 鈣鈦礦電池電動傳輸層材料 (PSCs HTM) 84
第四章結論 86
參考資料 89
附錄 97

參考文獻

Green, M. A.; Emery, K.; King, D. L.; Hishikawa, Y.; Warta, W. Prog. Photovoltaics, 2006, 14, 5, 455.
A, D. V.; Journal of Physics D: Applied Physics, 1980, 13, 5, 83.
Grätzel, M. Inorg. Chem., 2005, 44, 6841.
Ghosh, A. K.; Feng, T. Journal of Applied Physics, 1978, 49, 12, 5982.
Tang, C. W. Applied Physics Letters, 1986, 48, 183.
Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science, 1995, 270 (5243), 1789.
https://www.nrel.gov/pv/cell-efficiency.html (2023)
(a) NPG Asia Materials, 2010, 2, 96.;
(b) https://product.statnano.com/product/11739/amorphous-silicon-solar-cells (2022)
https://www.solarfeeds.com/mag/wiki/copper-indium-gallium-selenide/ (2022)
(a) https://www.pv-magazine.com/2020/12/11/semi-transparent-dye-sensitized-solar-module-with-8-7-efficiency/ (2022);
(b) https://www.pv-magazine.com/2020/03/24/an-organic-solar-cell-with-25-efficiency/ (2022);
(c) https://911electronic.com/de/perovskite-cells-efficient-and-cheaper/ (2022)
McEvoy, A.; Markvart, T.; Castañer, L. Practical Handbook of Photovoltaics (Second Edition), Academic Press., Switzerland, 2013.
Arkhipov, V. I.; Heremans, P.; Bässler, H. Appl. Phys. Lett., 2003, 82, 4605.
Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Chem. Rev., 2009, 109, 11, 5868.
Mazhari, B. Sol. Energy 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.
McEvoy, A.; Markvart, T.; Castañer, L. Practical Handbook of Photovoltaics (Second Edition), Academic Press., Switzerland, 2013.
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.
Haid, S.; Mishra, A.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Chem. Mater., 2011, 23, 4435.
Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater., 2011, 11, 44.
Chen, H. Y.; Hou, J. H.; Zhang, S. Q.; Liang, Y. Y.; Yang, G. W.; Yang, Y.; Yu, L. P.; Wu, Y.; Li, G. Nat. photonics, 2009, 3, 649.
He, Z. C.; Zhong, C. M.; Su, S. J.; Xu, M.; Wu, H. B.; Cao, Y. Nat. photonics, 2012, 6, 591.
Qin, Y. P.; Ye, L.; Zhang, S. Q.; Zhu, J.; Yang, B.; Ade, H.; Hou, J. H. J. Mater. Chem. A, 2018, 6, 4324.
Yun, J. H.; Park, S. M.; Heo, J. H.; Lee, H. S.; Yoon, S. W.; Kang, J. B.; Im, S. H.; Kim, H. J.; Lee, W. M.; Kim, B. S.; Ko, M. J.; Chung, D. S.; Son, H. J. Chem. Sci., 2016, 7, 6649.
Kan, B.; Li, M. M.; Zhang, Q.; Liu, F.; Wan, X. J.; Wang, Y. C.; Ni, W.; Long, G. K.; Yang, X.; Feng, H. R.; Zuo, Y.; Zhang, M. T.; Huang, F.; Cao, Y.; Russell, T. P.; Chen, Y. S. J. Am. Chem. Soc., 2015, 137, 3886.
Kroto, H. W.; Heath, J. R.; O’brien, S. C.; Curl, R. F.; Smalley, R. E. Nature, 1985, 318, 162.
Pfuetzner, S.; Meiss, J.; Petrich, A.; Riede, M.; Leo, K. Appl. Phys. Lett., 2009, 94, 223307.
(a) Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F. J. Org. Chem., 1995, 60, 532.;
(b) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science, 1995, 270, 1789.
He, Y.; Chen, H. Y.; Hou, J.; Li, Y. J. Am. Chem. Soc., 2010, 132, 1377.
Zhao, G. J.; He, Y. J.; Li, Y. F. Adv. Mater., 2010, 22, 4355.
Li, C.; Wonneberger, H. Adv. Mater., 2012, 24, 613.
Ye, L.; Sun, K.; Jiang, W.; Zhang, S. Q.; Zhao, W. C.; Yao, H. F.; Wang, Z. H.; Hou, J. H. ACS Appl. Mater. Interfaces, 2015, 7, 9274.
Sun, D.; Meng, D.; Cai, Y. H.; Fan, B. B.; Li, Y.; Jiang, W.; Huo, L. J.; Sun, Y. M.; Wang, Z. H. J. Am. Chem. Soc., 2015, 137, 11156.
Zhong, Y.; Kumar, B.; Oh, S. J.; Trinh, M. T.; Wu, Y.; Elbert, K.; Li, P. P.; Zhu, X. Y.; Xiao, S. X.; Ng, F.; Steigerwald, M. L.; Nuckolls, C. J. Am. Chem. Soc., 2014, 136, 8122.
Zhang, G.; Zhao, J.; Chow, P. C.; Jiang, K.; Zhang, J.; Zhu, Z.; Zhang, J.; Huang, F.; Yan, H. Chem. Rev., 2018, 118, 3447.
Holliday, S.; Ashraf, R. S.; Nielsen, C. B.; Kirkus, M.; Röhr, J. A.; Tan, C. H.; Collado-Fregoso, E.; Knall, A. C.; Durrant, J. R.; Nelson, J.; McCulloch, I. J. Am. Chem. Soc., 2015, 137, 898.
Holliday, S.; Ashraf, R. S.; Wadsworth, A.; Baran, D.; Yousaf, S. A.; Nielsen, C. B.; Tan, C. H.; Dimitrov, S. D.; Shang, Z. R. ; Gasparini, N.; Alamoudi, M.; Laquai, F.; Brabec, C. J.; Salleo, A.; Durrant, J. R.; McCulloch, I. Nat. Commun., 2016, 7, 11585.
Yuan, J.; Zhang, Y. Q.; Zhou, L. Y.; Zhang, G. C.; Yip, H. L.; Lau, T. K.; Lu, X. H.; Zhu, C.; Peng, H. J.; Johnson, P. A.; Leclerc, M.; Cao, Y.; Ulanski, J.; Li, Y. F.; Zou, Y. P. Joule, 2019, 3, 1140-1151.
Liu, Q. S.; Jiang, Y. F.; Jin, K.; Qin, J. Q.; Xu, J. G.; Li, W. T.; Xiong, J.; Liu, J. F.; Xiao, Z.; Sun, K.; Yang, S. F.; Zhang, X. T.; Ding, L. M. Science Bulletin., 2020, 65(4), 272.
Cui, Y., Xu, Y., Yao, H., Bi, P., Hong, L., Zhang, J., Zu, Y., Zhang, T., Qin, J., Ren, J., Chen, Z., He, C., Hao, X., Wei, Z., Hou, J., Adv. Mater., 2021, 33, 2102420.
Zhu, L.; Zhang, M.; Xu, J.; Li, C.; Yan, J.; Zhou, G.; Zhong, W.; Hao, T.; Song, J.; Xue, X.; Zhou, Z.; Zeng, R.; Zhu, H.; Chen, C. C.; MacKenzie, R. C. I.; Zou, Y.; Nelson, J.; Zhang, Y.; Sun, Y.; Liu, F. Nat. Mater., 2022, 21, 656–663.
43 https://www.nidek-intl.com/product/coating_technical/coating_technique_1.html (2022)
Sykes, M. E. Circumventing the Tradeoff between Optical Absorption and Exciton Diffusion in Organic Photovoltaics, 2015.
Voo, R.; Mariatti, M.; Sim, L. Journal of Plastic Film and Sheeting, 2011, 27(4), 331.
Kwon, Y. J.; Park, Y. D.; Lee, W. H. Materials, 2016, 9(8), 650.
Giri, G.; Verploegen, E.; Mannsfeld, S. C. B.; Atahan-Evrenk, S.; Kim, D. H.; Lee, S. Y.; Becerril, H. A.; Aspuru-Guzik, A.; Toney, M. F.; Bao, Z. N. Nature, 2011, 480, 504.
Gsänger, M.; Kirchner, E.; Stolte, M.; Burschka, C.; Stepaneko, V.; Pflaum, J.; Würthner, F. J. Am. Chem. Soc., 2014, 136, 6, 2351.
Calió, L., Kazim, S., Grätzel, M., & Ahmad, S. Angew. Chem. Int. Ed., 2016, 55, 14522.
Kojima, A.; Teshima, K.; Shirai, Y.; Miyasaka, T. J. Am. Chem. Soc., 2009, 131, 17, 6050.
OPTICS & PHOTONICS NEWS NOVEMBER 2020.
Marinova, N.; Valero, S.; Delgado, J. L. Journal of Colloid and Interface Science, 2017, 488, 373.
Hussain, I.; Tran, H. P.; Jaksik, J.; Moore, J.; Islam, N.; Uddin, M. J.; Emergent Materials, 2018, 1, 133.
Chen, C.; Liu, D. L.; Wu, Y. J.; Bi, W. B.; Sun, X. K.; Chen, X.; Liu, W.; Xu, L.; Song, H. W.; Dai, Q. L. Nano Energy, 2018, 53, 849.
Choi, H.; Liu, X. Y.; Kim, H. L.; Kim, D.; Park, T. Adv. Energy Mater., 2021, 11, 2003829.
Qin, M. C.; Cao, J.; Zhang, T. K.; Mai, J. Q.; Lau, T. K.; Zhou, S.; Zhou, Y.; Wang, J. Y.; Hsu, Y. J.; Zhao, N.; Xu, J. B.; Zhan, X. W.; Lu, X. H. Adv. Energy Mater., 2018, 1703399.
Song, C. J.; Li, X. D.; Wang, Y. M.; Fu, S.; Wan, L.; Liu, S. Y.; Zhang, W. J.; Song, W. J.; Fang, J. F. J. Mater. Chem. A, 2019, 7, 19881.
Afraj, S. N.; Velusamy, A.; Chen, C. Y.; Ni, J. S.; Ezhumalai, Y.; Pan, C. H.; Chen, K. Y.; Yau, S. L.; Liu, C. L.; Chiang, C. H.; Wu, C. G.; Chen, M. C. J. Mater. Chem. A, 2022, 10, 11254.
Kim, H. S.; Lee, C. R.; Im, J. H.; Lee, K. B.; Moehl, T.; Marchioro, A.; Moon, S. J.; Robin H. B.; Yum, J. H.; Moser, J. E.; Grätzel M.; Park N. G. Sci Rep., 2012, 2, 591.
Chen, Y, C.; Huang, S, K.; Li, S, S.; Tsai, Y, Y.; Chen, C, P.; Chen, C, W.; Chang, Y, J.; ChemSusChem, 2018, 11, 3225-3233
Deng, Z.; He, M.; Zhang, Y.; Ullah, F.; Ding, K.; Liang, J.; Zhang, Z.; Xu, H.; Qiu, Y.; Xie, Z.; Shan, T.; Chen, Z.; Zhong, H.; Chen, C, C. Chem. Mater., 2021, 33, 285.
Cho, I.; Jeon, N.; Kwon, O.; Kim, D.; Jung, E.; Noh, J.; Seo,
J.; Seok, S.; Park, S. Chem. Sci., 2017, 8, 734.
Wang, Y, K.; Ma, H.; Chen, Q.; Sun, Q.; Liu, Z.; Sun, Z.; Jia, X.; Zhu, Y.; Zhang, S.; Zhang, J.; Yuan, N.; Ding, J.; Zhou, Y.; Song, Bo.; Li, Y.; ACS Appl. Mater. Interfaces, 2021, 13, 7705–7713.
Zhang, F.; Yao, Z.; Guo, Y.; Li, Y.; Bergstrand, J.; Brett, C. J.; Cai, B.; Hajian, A.; Guo, Y.; Yang, X.; Gardner, J. M.; Widengren, J.; Roth, S. V.; Kloo, L.; Sun, L. J. Am. Chem. Soc., 2019, 141, 19700.
Sun, X.; Li, Z.; Yu, X.; Wu, X.; Zhong, C.; Liu, D.; Lei, D.; Jen, A. K. Y.; Li, Z.; Zhu, Z. Angew. Chem. Int. Ed., 2021, 60, 7227 – 7233
Huang, C. Y.; Liao, X. F.; Gao, K.; Zuo, L. J.; Lin, F.; Shi, X. L.; Li, C. Z.; Liu, H. B.; Li, X. S.; Liu, F.; Chen, Y. W.; Chen, H. Z.; Jen, A. K. Y. Chem. Mater., 2018, 30(15), 5429.
Zhao, W.; Li, S.; Yao, H.; Zhang, S.; Zhang, Y.; Yang, B.; Hou, J. J. Am. Chem. Soc., 2017, 139, 7148-7151.
Joseph, V.; Xia, J. X.; Sutanto, A. A.; Jankauskas, V.; Momblona, C.; Ding, B.; Rakstys, K.; Balasaravanan, R.; Pan, C. H.; Ni, J. S.; Yau, S. L.; Sohail, M.; Chen, M. C.; Dyson, P. J.; Nazeeruddin, M. K. ACS Appl. Mater. Interfaces., 2022, 14 (19), 22053-22060.
Xia, J. X.; Joseph, V.; Sutanto, A. A.; Balasaravanan, R.; Ezhumalai, Y.; Zhang, Z. X.; Ni, J. S.; Tingare, Y. S.; Yau, S.L.; Shao, G.; Qiu, Z. L.; Asiri, A. M.; Chen, M. C.; Nazeeruddin, M. K. Cell Reports Physical Science, 2023, 4, 101312.

指導教授

陳銘洲(Ming-Chou Chen)

審核日期

2023-6-28

推文