可溶性具硫醚鏈醌型聯噻吩與多併環噻吩衍生物有機薄膜電晶體材料之開發;Development of Solution Processable Thioalkylated Oligothiophenes and Fused Thiophenes for Organic Thin Film Transistors

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/73945

Title:	可溶性具硫醚鏈醌型聯噻吩與多併環噻吩衍生物有機薄膜電晶體材料之開發;Development of Solution Processable Thioalkylated Oligothiophenes and Fused Thiophenes for Organic Thin Film Transistors
Authors:	連偉傑;Lien, Wei-Chieh
Contributors:	化學學系
Keywords:	有機薄膜電晶體;多併環噻吩;可溶性具硫醚鏈;醌型聯噻吩;Solution Processable;Thioalkylated Oligothiophenes;Fused Thiophenes;Organic Thin Film Transistors
Date:	2017-07-05
Issue Date:	2017-10-27 12:55:32 (UTC+8)
Publisher:	國立中央大學
Abstract:	延續實驗室之前開發具硫醚鏈噻吩的研究，開發出五大系列核心主體 TTAR 系列、DTDSTQ 系列、DDTT-DTDST 系列、DT-TSBTQ 系列與 DDTT-TSBT 系列。第一系列 TTAR 裏延續實驗室已開發的 TTAR 核心，末端以n三併環噻吩封端 (DDTT-TTAR)，在 p-type 電性表現已達到 0.80 cm2V-1s-1，故藉由改變末端共軛單元來增加 π 電子傳遞，開發出 DbT-TTAR (1) 與 DTVT-TTAR (2) 使共軛長度增加，HOMO 能階上升，並有效降低分子能階，來提高電性表現。第二系列 DTDSTQ 裏延續實驗室已開發的 DTDST 核心，DTDSTQ-14 與 DTDSTQ-6 在 n-type 電性表現已達到 0.408 和 0.045 cm2V-1s-1，藉由改變硫醚碳鏈長度來改善此系列分子的溶解度與分子排列性，開發出 DTDSTQ-10 (3) 進而研究 chain effect 所帶來的影響，在這其中也得到 DTDSTQ 與 DTDRTQ 核心之單晶結構，近而證明透過硫原子的引入，能有效幫助分子排列。第三系列 DDTT-DTDST 裏，比較實驗室已開發的三併環噻吩，分別帶兩條長直硫醚碳鏈與帶長直碳鏈，末端皆以三併環噻吩封端的 DDTT-DSDTT-10 與 DDTT-DTTR2，在 p-type 電性表現已達到 2.2 和 0.01 cm2V-1s-1 延續實驗室已開發的 DTDST 核心，藉由改變核心共軛長度，增加未定域化面積來降低分子能階，末端也以三併環噻吩封端 DDTT-DTDST-14 (4)，預期能比目前全台灣 p-type 小分子材料 DDTT-DSDTT-10 之電性 2.2 cm2V-1s-1，有更好的表現。第四系列 DDTT-TSBT 裏延續實驗室已開發之四條硫醚鏈 TSBTQ 目前再 n- type 小分子材料已有不錯的表現，在這其中也得到 TSBTQ 核心之單晶結構，證明其核心具有良好的排列性，合成以 TSBT 為核心，末端以三併環噻吩封端封端的 DDTT-TSBT-6 與 DDTT-TSBT-10，預期在 p-type 小分子材料也有不錯的電性表現。第五系列 DT-TSBTQ 裏延續實驗室已開發之四條硫醚鏈 TSBTQ 目前再 n-type 小分子材料已有不錯的表現，希望藉由增加核心共軛長度，合成高平面性且低能階的 n-type 小分子材料，使電性能有更好的表現。 ;Seven small molecular organic semiconductors, DbT-TTAR (1), DTVT-TTAR (2), DTDSTQ-10 (3), DDTT-DTDST-14 (4), DDTT-TSBT-10 (5), DT-TSBTQ-6 (6), and DT-TSBTQ-10 (7) have been synthesized for organic thin film transistors (OTFTs). For the first series, DDTT-TTAR exhibited a high p-channel mobilities of up to 0.8 cm2V-1s-1. To further elaborate this study, we have synthesized two new p-type derivatives, DbT-TTAR (1) and DTVT-TTAR (2) for comparison. For the second series, DTDSTQ with different alkyl chains exhibited mobility of 0.045 (DTDSTQ-6) to 0.408 cm2V-1s-1 (DTDSTQ-14) via solution shearing. To complete this study, DTDSTQ-10 (3) was synthesized for comparison. In addition, DTDSTQ-14 and DTDRTQ-14 molecular structures were determined by single crystal X-ray diffraction, which shows that the molecular arrangement of the quinoidal structures were significantly changed with the introduction of thioalkyl chains compared to the normal alkyl chains. For the third series, DDTT-DSDTT-10 exhibited very high p-channel mobility of 2.2 cm2V-1s-1. With the dithioalkyl terthiophene (DTDST) in hand, the dithienothiophenyl end-capped DDTT-DTDST-14 (4) are prepared for comparison. For the fourth series, tetra thioalkylated bithiophene-based unit (TSBT) was served as the central core and are ends capped with dithienothiophene to give the potential p-type DDTT-TSBT-10 (5). Finally, TSBT-based quinoids, TSBTQ-6 and TSBTQ-14 were developed and exhibit a n-channel mobility of 0.09 cm2V-1s-1 via solution shearing. Therefore, more conjugated DT-TSBTQ-6 (6) and DT-TSBTQ-10 (7) are developed for OTFT.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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