環戊烷二噻吩與雙噻吩醯亞胺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：20

、訪客IP：18.117.183.175

姓名

林意慈(Yi-Ci Lin) 查詢紙本館藏

畢業系所

化學學系

論文名稱

環戊烷二噻吩與雙噻吩醯亞胺衍生物之有機光電材料開發
(Development of Cyclopentadithiophene (CDT) and Bithiophene-imide (BTI) Derivatives for 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 (2027-7-20以後開放)

摘要(中)

本論文主要為有機光伏電池 (OPVs) 的材料開發。本研究成功開發出一系列之非富勒烯受體 (non fullerene acceptor, NFA) 材料，以雙噻吩醯亞胺 (bithiophene-imide, BTI) 為核心，先接上環戊烷二噻吩(cyclopentadithiophene, CDT) 作為 -spacer，再外接四種不同拉電子單元：茚酮 (indanone, IN)、二氯茚酮 (dichlorodicyanomethylene indanone, INCl)、二溴茚酮 (dibromodicyanomethylene indanone, INBr) 與二氰乙烯基 (dicyanovinyl, DCV)，製備出 IN-CDT-BTI-b20 (1)、INCl-CDT-BTI-b20 (2)、INBr-CDT-BTI-b20 (3) 與 DCV-CDT-BTI-b20 (4)等四個化合物。
BTI 為具有強拉電子基團醯亞胺的缺電子受體單元，且有較高的分子平面性和良好的溶解度，預期此核心與多併環噻吩搭配而成之九環結構有助於電荷傳遞。之後於此核心接上具氯、溴等鹵素之末端基團，對材料之能階及UV-vis吸收進行調控。
材料已藉由 DPV 及 UV-Vis 測定其電化學及光學性能 (HOMO/LUMO 與Eg)，並透過 TGA 及 DSC 檢測其熱穩定性，新開發之四種 NFA 材料將會應用於有機光伏電池 (OPV) 及鈣鈦礦太陽能電池 (PSC)。

摘要(英)

A new series of bithiophene-imide (BTI) -based organic photoelectronic materials were synthesized and characterized for the applications in organic photovoltaic cells (OPVs).
With high molecular planarity and solubility, BTI were used as central units and coupled with cyclopentadithiophene (CDT) to develop new conjugated cores CDT-BTI. Then, the new nine-ring system was end-capped with various electron-withdrawing groups, such as dicyanomethylene indanone (IN), dichlorodicyanomethylene indanone (INCl), dibromodicyanomethylene indanone (INBr) and dicyanovinyl (DCV), via Knoevenagel condensation, yielding four new compounds, IN-CDT-BTI-b20 (1), INCl-CDT-BTI-b20 (2), INBr-CDT-BTI-b20 (3), and DCV-CDT-BTI-b20 (4), respectively. In addition to the application in OPV, these newly developed non-fullerene acceptors could also be used as passivating agents in PSCs based on our recent studies.
The optical and electrochemical properties (HOMO and LUMO) of these newly synthesized compounds were characterized by UV-vis and DPV. Thermal properties were investigated by DSC and TGA. Currently, optoelectronic devices based on these newly developed organic photoelectronic materials are under examination and optimization.

關鍵字(中)

★ 非富勒烯受體
★ 有機光伏打太陽能電池
★ 鈣鈦礦太陽能電池

關鍵字(英)

★ non fullerene acceptor
★ Organic Photovoltaics solar cell
★ perovskite solar cells

論文目次

摘要 ......................................................................................................... i
Abstract .................................................................................................... vii
謝誌 ..................................................................................................... viii
目錄 ....................................................................................................... ix
List of Figures ......................................................................................... xiii
List of Schemes ....................................................................................... xiv
List of Tables ............................................................................................ xv
附錄目錄 ................................................................................................. xvi
第一章緒論 ............................................................................................... 1
1-1 前言 .................................................................................................. 2
1-2 有機太陽能電池之概論 .................................................................. 3
1-2-1 矽晶太陽能電池 ...................................................................... 4
1-2-2 無機化合物半導體太陽能電池 ............................................. 5
1-2-3 有機太陽能電池 ...................................................................... 6
1-3 有機光伏打電池之基本元件組成 .................................................. 7
1-4 有機光伏打電池之運作原理 .......................................................... 8
1-4-1 光子吸收 (Optical absorption) ............................................... 9
1-4-2 激子擴散與分離 (Exction diffusion and dissociation) .......... 9
1-4-3 電荷傳輸 (Charge transfer) .................................................. 10
x
1-4-4 電荷收集 (Charge collection)............................................... 10
1-5 有機光伏打電池之元件演變 ........................................................ 10
1-5-1 雙層式異質接面 (Bilayer heterojunction, PHJ) .................. 11
1-5-2 體異質接面 (Bulk heterojunction, BHJ) ............................ 11
1-5-3 串聯結構 ................................................................................ 12
1-6 有機光伏打電池參數介紹 ............................................................ 12
1-6-1 J-V 曲線 ................................................................................. 14
1-6-2 短路電流 (Short circuit current, JSC) .................................... 14
1-6-3 開環電壓 (Open circuit voltage, VOC) .................................. 15
1-6-4 外部量子效率 (Eternal quantum efficiency, EQE) ............. 15
1-6-5 填充因子 (Fill factor, FF)..................................................... 16
1-6-6 能量轉換效率 (Power conversion efficiency, η, PCE) ....... 16
1-7 有機光伏打電池材料 .................................................................... 16
1-7-1 P-type 有機光伏打材料 (Donor) ......................................... 16
1-7-2 N-type 有機光伏打材料 (Acceptor) .................................... 20
1-8 鈣鈦礦太陽能電池簡介 ................................................................ 28
1-8-1 基本構造 ................................................................................ 30
1-8-2 工作原理 ................................................................................ 32
1-8-3 電洞傳輸層 ............................................................................ 32
1-9 有機薄膜的製備方式 .................................................................... 35
1-9-1 氣相沉積 ................................................................................ 35
1-9-2 液相沉積 ................................................................................ 36
xi
1-10 研究動機與目的 .......................................................................... 38
第二章實驗部份 ..................................................................................... 41
2-1 化合物名稱對照 ............................................................................ 42
2-2 實驗藥品 ........................................................................................ 44
2-3 實驗儀器 ........................................................................................ 46
2-4 合成步驟 ........................................................................................ 50
3,3′-dibromo-2,2′-bithiophene (5) 之合成 ....................................... 50
dithieno[3,2-c:2′,3′-e]oxepine-4,6-dione (7) 之合成 ....................... 51
2-octyldodecan-1-amine (10) 之合成 ............................................. 52
5-(2-octyldodecyl)-4H-dithieno[3,2-c:2′,3′-e]azepine-4,6(5H)-dione (12, BTI-b20) 之合成 ...................................................................... 54
2,8-dibromo-5-(2-octyldodecyl)-4H-dithieno[3,2-c:2′,3′-e]azepine-4,6(5H)-dione (13, diBr-BTI-b20) 之合成 ..................................... 56
3-bromo-2,2′-bithiophene (16, 3-BrBT)之合成 ............................... 57
bis(4-((2-ethylhexyl)oxy)phenyl)methanone (17, BP-Ob8) 之合成........................................................................................................... 59
4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (19, CDT-b8) 之合成 .............................................. 60
(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-2-yl)trimethylstannane (20, CDT-b8-Me3Sn) 之合成........................................................................................................... 61
xii
2,8-bis(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-2-yl)-5-(2-octyldodecyl)-4H-dithieno[3,2-c:2′,3′-e]azepine-4,6(5H)-dione (21, CDT-BTI-b20) 之合成 .................... 62
6,6′-(5-(2-octyldodecyl)-4,6-dioxo-5,6-dihydro-4H-dithieno[3,2-c:2′,3′-e]azepine-2,8-diyl)bis(4,4-bis(4-((2-ethylhexyl)oxy)phenyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde) ............... 64
2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (23, IN) 之合成 .................................................................................................. 65
2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (25, INCl) 之合成 ......................................... 66
2-(5,6-dibromo-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (29, INBr) 之合成 ......................................... 67
IN-CDT-BTI-b20 (1) 之合成 .......................................................... 71
INCl-CDT-BTI-b20 (2) 之合成 ....................................................... 72
INBr-CDT-BTI-b20 (3) 之合成 ....................................................... 73
DCV-CDT-BTI-b20 (4) 之合成 ...................................................... 74
第三章結果與討論 ................................................................................. 76
3-1 有機光電材料之光學性質探討 .................................................... 77
3-2 有機光電材料之電化學性質探討 ................................................ 81
3-3 有機光電材料之熱穩定性分析 .................................................... 84
第四章結論 ............................................................................................. 87
附錄 ........................................................................................................... 97

參考文獻

Grätzel, M. Inorg. Chem. 2005, 44, 6841-6851.
Chapin, D. M.; Fuller, C. C.; Person, G. L. J. Appl. Phys. 1954, 25, 676-677.
Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater. 2011, 11, 44-48.
https://www.nrel.gov/pv/cell-efficiency.htmL
Marinova, N.; Valero, S.; Delgado, J. L. J. Colloid Interface Sci. 2017, 488, 373-389.
McEvoy, A.; Markvart, T.; Castaner, L. Practical Handbook of Photovoltaics (Second Edition), Academic Press., Switzerland, 2011.
Arkhipov, V. I.; Heremans, P.; Bässler, H. Appl. Phys. Lett. 2003, 82, 4605.
Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science, 1992, 258, 1474-1476.
Mazhari, B. Sol. Energ Mat. Sol. C. 2006, 90, 1021-1033.
Boudreault, P. L. T.; Najari, A.; Leclerc, M. Chem. Mater. 2011, 23, 456-469.
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, 374-380.
Schulze, K.; Riede, M.; Brier, E.; Reinold, E.; Bäuerle, P.; Leo, K. J. Appl. Phys. 2008, 104, 074511.
Sakai, J.; Taima, T.; Yamanari, T.; Saito, K. Sol. Energy Mater. Sol. C. 2009, 93, 1149.
Zhou, J.; Wan, X.; Liu, Y.; Long, G.; Wang, F.; Li, Z.; Zuo, L.; Li C.; Chen, Y. Chem. Mater. 2011, 23, 4666-4668.
Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater. 2011, 11, 44-48.
Chen, H. Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. photonics, 2009, 3, 649-653.
He, Z.; Zhong, C.; Su, S.; Xu, M.; Wu, H.; Cao, Y. Nat. photonics, 2012, 6, 591-595.
Qin, Y.; Ye, L.; Zhang, S.; Zhu, J.; Yang, B.; Ade, H.; Hou, J. J. Mater. Chem. A, 2018, 6, 4324-4330.
Arai, R.; Furukawa, S.; Hidaka, Y.; Komiyama, H.; Yasuda, T. ACS Appl. Mater. Interfaces, 2019, 11, 9259-9264.
Arai, R.; Furukawa, S.; Sato, N.; Yasuda, T. J. Mater. Chem. A, 2019, 7, 20187-20192.
Kroto, H. W.; Heath, J. R.; Obrien, S. C.; Curl, R. F.; Smalley, R. E. Nature, 1985, 318, 162-163.
Pfuetzner, S.; Meiss, J.; Petrich, A.; Riede, M.; Leo, K. Appl. Phys. Lett. 2009, 94, 223307.
Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F.; Yao, J.; Wilkins, C. L. J. Org. Chem. 1995, 60, 532-538.
He, Y.; Chen, H. Y.; Hou, J.; Li, Y. J. Am. Chem. Soc. 2010, 132, 1377-1382.
Zhao, G.; He, Y.; Li, Y. Adv. Mater. 2010, 22, 4355-4358.
Dittmer, J. J.; Petritsch, K.; Marseglia, E. A.; Friend, R. H.; Rost, H.; Holmes, A. B. Synth.Met. 1999, 102, 879-880.
Sharenko, A.; Proctor, C. M.; van der Poll, T. S.; Henson, Z. B.; Nguyen, T. Q.; Bazan, G. C. Adv. Mater. 2013, 25, 4403-4406.
Singh, R.; Aluicio-Sarduy, E.; Kan, Z.; Ye, T.; MacKenzie, R. C. I.; Keivanidis, P. E. J. Mater. Chem. A 2014, 2, 14348-14353.
Cai, Y.; Huo, L.; Sun, X.; Wei, D.; Tang, M.; Sun, Y. Adv. Energy Mater. 2015, 5, 1500032.
Jiang, W.; Ye, L.; Li, X.; Xiao, C.; Tan, F.; Zhao, W.; Hou, J.; Wang, Z. Chem. Commun. 2014, 50, 1024-1026.
Sun, D.; Meng, D.; Cai, Y.; Fan, B.; Li, Y.; Jiang, W.; Hou, L.; Sun, Y.; Wang, Z. J. Am. Chem. Soc. 2015, 137, 11156-11162.
Meng, D.; Sun, D.; Zhong, C.; Liu, T.; Fan, B.; Huo, L.; Li, Y.; Jiang, W., Choi, H.; Kim, T.; Kim, J. Y.; Sun, Y.; Wang, Z. H.; Heeger, A. J. J. Am. Chem. Soc. 2016, 138, 375-380.
Zhang, G.; Zhao, J.; Chow, P. C.; Jiang, K.; Zhang, J.; Zhu, Z.; Zhang, J.; Huang, F.; Yan, H. Chem. Rev. 2018, 118, 3447-3507.
Winzenberg, K. N.; Kemppinen, P.; Scholes, F. H.; Collis, G. E.; Shu, Y.; Singh, T. B.; Bilic, A.; Forsyth, C. M.; Watkins, S. E. Chem. Commun. 2013, 49, 6307-6309.
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, 898-904.
Zhang, H.; Liu, Y.; Sun, Y.; Li, M.; Ni, W.; Zhang, Q.; Wan, X.; Chen, Y. Sci. China Chem. 2017, 60, 366-369.
Lin, Y.; Wang, J.; Zhang, Z. G.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. Adv. Mater. 2015, 27, 1170-1174.
Yang, Y.; Zhang, Z. G.; Bin, H.; Chen, S.; Gao, L.; Xue, L.; Yang, C.; Li, Y. F. J. Am. Chem. Soc. 2016, 138, 15011-15018.
Zhao, W.; Li, S.; Yao, H.; Zhang, S.; Zhang, Y.; Yang, B.; Hou, J. J. Am. Chem. Soc. 2017, 139, 7148-7151.
Wan, J.; Zhang, L.; He, Q.; Liu, S.; Huang, B.; Hu, L.; Zhou, W.; Chen, Y. Adv. Funct. Mater. 2020, 30, 1909760.
Li, S.; Li, C. Z.; Shi, M.; Chen, H. ACS Energy Letters, 2020, 5, 1554- 1567.
Liu, Q.; Jiang, Y.; Jin, K.; Qin, J.; Xu, J.; Li, W.; Xiong, J.; Liu, J.; Xiao, Z.; Sun, K.; Yang, S.; Zhang, X.; Ding, L. Sci. Bull. 2020, 65, 272-275.
Chen, Y.; Zhang, L.; Zhang, Y.; Gao, H.; Yan, H. RSC Adv. 2018, 8, 10489-10508.
Kojima, A.; Teshima, K.; Shirai, Y.; Miyasaka, T. J. Am. Chem. Soc. 2009, 131, 6050-6051.
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.; Grätzel, M.; Park, N. G. Sci. Rep. 2012, 2, 1-7.
Jiang, Q.; Chu, Z.; Wang, P.; Yang, X.; Liu, H.; Wang, Y.; Yin, Z.; Wu, J.; Zhang, X.; You, J. Adv. Mater. 2017, 29(46), 1703852.
Tian, X.; Stranks, S. D.; You, F. Sci. Adv. 2020, 6(31), eabb0055.
https://www.pv-magazine.com/2021/04/06/unist-epfl-claim-25-6-efficiency-world-record-for-perovskite-solar-cell/
Song, Z.; Watthage, S. C.; Phillips, A. B.; Heben, M. J. J. Photonics Energy, 2016, 6, 022001.
Wu, Y.; Yang, X.; Chen, W.; Yue, Y.; Cai, M.; Xie, F.; Han, L. Nature Energy, 2016, 1, 1-7.
陳彥均, 不同膜厚之電子傳輸及電洞注入層對有機發光二極體之性質影響分析. 聖約翰科技大學自動化及機電整合研究所碩士學位論文, 2011.
Wang, J.; Wang, S.; Li, X.; Zhu, L.; Meng, Q.; Xiao, Y.; Li, D. Chem. Commun. 2014, 50, 5829-5832.
Kang, M. S.; Sung, S. D.; Choi, I. T.; Kim, H.; Hong, M.; Kim, J.; Lee, W. I.; Kim, H. K. ACS Appl. Mater. Interfaces, 2015, 7, 22213-22217.
Feng, J. Y.; Lai, K. W.; Shiue, Y. S.; Singh, A.; Kumar, C. P.; Li, C. T.; Wu, W. T.; Lin, J. T.; Chu, C. W.; Chang, C. C.; Su, C. C. J. Mater. Chem. A, 2019, 7, 14209-14221.
Wang, Y.; Chen, W.; Wang, L.; Tu, B.; Chen, T.; Liu, B.; Yang, K.; Chang, W. K.; Zhang, X.; Sun, H. L.; Chen, G. C.; Feng, X.; Woo, H. Y.; Djurišic´, A. B.; He, Z.; Guo, X. Adv. Mater. 2019, 1902781.
Sun, X.; Deng, X.; Li, Z.; Xiong, B.; Zhong, C.; Zhu, Z.; Li, Z.; Jen, K. Y. ACS Appl. Mater. Interfaces, 2020, 12, 32712-32718.
Liang, Y.; Chen, Z.; Jing, Y.; Rong, Y.; Facchetti, A.; Yao, Y. J. Am. Chem. Soc. 2015, 137, 4956-4959.
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. Nature, 2011, 480, 504-508.
Shi, Y. Q.;Chen, W.; Wu Z.; Wang, Y.; Sun, W. P.; Yang, K.; Tang, Y. M.; Woo, H. Y.; Zhou, M.; Djurišić, A. B.; He, Z. B.; Guo, X. G. J. Mater. Chem. A, 2020, 8, 13754-13762.
Luo, D.; Li, L. Q.; Shi, Y. Q.; Zhang, J. Q.; Wang, K.; Guo, X. G.; Aung Ko Ko Kyaw. J. Mater. Chem. A, 2021, 9, 14948-14957.

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, 11254-11267.

指導教授

陳銘洲(Ming-Chou Chen)

審核日期

2022-7-29

推文