可溶性具硫鏈環戊烷二?吩衍生物 有機光電材料之開發

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/85725

Title:	可溶性具硫鏈環戊烷二?吩衍生物有機光電材料之開發
Authors:	黃品瑜;Huang, Ping-Yu
Contributors:	化學學系
Keywords:	有機薄膜電晶體;有機光伏打電池;電洞傳輸層;OTFT;OPV;HTL
Date:	2021-07-28
Issue Date:	2021-12-07 11:19:32 (UTC+8)
Publisher:	國立中央大學
Abstract:	本論文主要可以分為有機薄膜電晶體 (OTFTs)、有機光伏打電池 (OPVs) 和電洞傳輸層 (HTLs) 的材料開發。　　有機薄膜電晶體 (OTFTs) 的部分，本研究成功以具硫鏈之環戊烷二?吩衍生物 (CDTS) 為核心，開發出三種不同碳鏈之?型結構，包含 CDTSQ-8 (1)、CDTSQ-10 (2) 和 CDTSQ-12 (3)。同時，將拉電子基團 INCl 接上核心CDTS，開發出另一種 OTFTs 材料 INClCDTS-10 (4)。其中 CDTSQ-10 (2) 及 CDTSQ-12 (3) 已取得晶體確定分子結構，發現分子間存在硫···氮作用力，使得分子間堆疊緊密。目前 CDTSQ-10 (2) 之載子移動率達 0.1 cm2V-1s-1，其餘分子仍在進行元件測試中。　　有機光伏打電池 (OPVs) 的部分，本研究利用所發現合成不同位向之 5-CHO-TSRBr (30) 及 4-CHO-TSRBr (31) 的反應條件，將 CDT 及 CDTS 進一步擴環，使 TCDT 及 TCDTS 核心接上不同位置的醛基，再分別於末端接上拉電子基團 IN 與 INCl，共開發出八種可溶性有機光伏打電池材料。TCDT 核心包括 IN-TCDT (5)、INCl-TCDT (6)、4-IN-TCDT (7) 及 4-INCl-TCDT (8)，而 TCDTS核心包括 IN-TCDTS (9)、INCl-TCDTS (10)、4-IN-TCDTS (11) 及 4-INCl-TCDTS (12)，目前正進行其 OPV 元件之測試。　　最後，在電洞傳輸層 (HTLs) 的部分，本研究將 CDTS 核心以 D-A-D 設計為基礎，兩側外掛 TPA推電子基團，開發出一種新型電洞傳輸層材料 CDTS-2D (14)，同時合成出 CDT-2D (13) 進行比較。經測量發現 CDTS-2D (14) 的energy gap比 CDT-2D (13) 縮小許多。CDTS-2D (14) 作為添加劑應用於 Pb-based 的鈣鈦礦太陽能電池目前初步測試具有 14.04 % 之光電轉換效率。　　這些新材料經由 UV-vis 及 DPV 測量其光學及電化學性質(HOMO、LUMO 能階)，且經 DSC 及 TGA 測量其熱穩定性，而使用這些新開發的小分子材料所應用之光電元件正在優化中。 ;A series of new organic optoelectronic materials were synthesized and characterized for organic thin film transistors (OTFTs), organic photovoltaic cells (OPVs), and hole transporting layers (HTLs). For the OTFTs, CDTS-based quinoidals with three different alkyl chains, CDTSQ-8 (1), CDTSQ-10 (2) and CDTSQ-12 (3) were synthesized. At the same time, the electron withdrawing group INCl was connected to the core (CDTS) to give INClCDTS-10 (4). Single-crystal X-ray diffraction of CDTSQ-10 (2) and CDTSQ-12 (3) have obtained and reveal intermolecular interaction between S and N, which promote a tight molecular stacking. Currently, via solution shearing, CDTSQ-10 (2) exhibits the best n-channel transport with the highest mobility up to 0.1 cm2V-1s-1. Optoelectronic devices based on these new developed small molecules are under examination and optimization. For the organic photovoltaics, 2-bromo-3-thioalkylthiophene were formylated to give isomeric 4- and 5-CHO-TSRBr in two different reaction conditions. Further, both new units were coupled with CDT and CDTS to give four new cores, TCDT and TCDTS. Lastly, the above four cores were end-capped with two electron withdrawing groups, IN and INCl, to give IN-TCDT (5), INCl-TCDT (6), 4-IN-TCDT (7) and 4-INCl-TCDT (8) for the TCDT series and IN-TCDTS (9), INCl-TCDTS (10), 4-IN-TCDTS (11) and 4-INCl-TCDTS (12) for the TCDTS series. Finally, one new CDTS-based hole transporting molecule was developed, where the CDTS core was end-capped with triphenylamino (TPA) unit. For comparison, CDT-based hole transporting molecule CDT-2D (13) was synthesized. It is found that the energy gap of CDTS-2D (14) is much smaller than CDT-2D (13). Currently, CDTS-2D (14) as additive exhibits power conversion efficiency of 14.04% in Pb-based PSC. The optical and electrochemical properties (HOMO and LUMO) of these new materials were characterized by UV-vis and DPV. Thermal properties were investigated by DSC and TGA. Optoelectronic devices used these new developed small molecules are under optimization.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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