噻吩並吡咯酮二聚體與雙噻吩並吡咯之有機光電材料開發;Development of Thienoisoindigo (TII) and Dithienopyrrole (DTP)  Derivatives of Organic Optoelectronic Applications

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/89155

Title:	噻吩並吡咯酮二聚體與雙噻吩並吡咯之有機光電材料開發;Development of Thienoisoindigo (TII) and Dithienopyrrole (DTP) Derivatives of Organic Optoelectronic Applications
Authors:	劉欣宜;Liu, Hsin-Yi
Contributors:	化學學系
Keywords:	有機光伏打電池;非富勒烯受體;有機薄膜電晶體;有機場效電晶體;有機半導體;Organic photovoltaic solar cell;Non-fullerene acceptor;Organic thin film transistor;Organic field effect transistor;Organic semiconductor
Date:	2022-07-28
Issue Date:	2022-10-04 10:59:47 (UTC+8)
Publisher:	國立中央大學
Abstract:	本論文研究主要分為有機光伏打電池 (Organic Photovoltaic, OPV) 與有機薄膜電晶體 (Organic Thin Film Transistor, OTFT) 的材料開發。有機光伏打電池 (OPV) 的部分，本研究成功開發出兩個系列之非富勒烯 (Nonfullerene acceptor, NFA) 材料，第一個系列以噻吩並吡咯酮二聚體 (Thienoisoindigo, TII) 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，開發出 IN-CDT-TII (1)、INCl-CDT-TII (2)、INBr-CDT-TII (3)、DCV-CDT-TII (4) 等四個有機分子。第二個系列則是以雙噻吩並吡咯 (Dithienopyrrole, DTP) 為核心，接上 CDT 後，再外接四種不同拉電子單元，製備出 IN-CDT-DTP (5)、INCl-CDT-DTP (6)、INBr-CDT-DTP (7)、DCV-CDT-DTP (8) 等四個材料。經由末端茚酮引入氯、溴等鹵素進行前置軌域能階之調控。此八種新開發之 NFA 材料未來將應用於 OPV，也會測試其作為添加劑應用於鈣鈦礦太陽能電池 (Perovskite solar cell, PSC)。 ii 本研究亦同時以具苯基烷氧鏈之 DTPP 為核心，開發可進行溶液製程之醌型 DTPPQ-16 (9) 與 DCV-DTPP-16 (10) 有機薄膜電晶體材料，目前正進行其作為 n-type OTFT 元件之測試。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。;Two series of new small molecules were synthesized and characterized for the applications in organic thin-film transistors (OTFTs), organic photovoltaic cells (OPVs), and perovskite solar cells (PSCs). N-substituted highly planar thienoisoindigo (TII) and dithienopyrrole (DTP) building blocks were used as central units and coupled with cyclopentadithiophene (CDT) to develop new conjugated cores CDT-TII and CDT-DTP, respectively. Further, these conjugated cores were 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 target compounds, IN-CDT-TII (1), INCl-CDT-TII (2), INBr-CDT-TII (3), DCV-CDT-TII (4), IN-CDT-DTP (5), INCl-CDT-DTP (6), INBr-CDT-DTP (7), and DCV-CDT-DTP (8), 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. For the OTFT materials development, DTPP-based quinoidal DTPPQ-16 (9) and DCV end-capped DCV-DTPP-16 (10) were synthesized for comparative study. 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.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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