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雙苯炔衍生物的合成及其場效電晶體應用 = Synthesis of Bi...

吳昭霖

雙苯炔衍生物的合成及其場效電晶體應用 = Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application

紀錄類型:	書目-語言資料,印刷品 : 單行本
並列題名:	Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application
作者:	吳昭霖,
其他團體作者:	國立高雄大學
出版地:	[高雄市]
出版者:	撰者;
出版年:	民99[2010]
面頁冊數:	146面圖，表 : 30公分;
標題:	二苯炔
標題:	bisbenzyne
電子資源:	http://handle.ncl.edu.tw/11296/ndltd/72722854560748852849
摘要註:	有機分子一直給人的印象是絕緣的物質，但自從白川英樹教授發現共軛有機分子也可以導電後，有機半導體材料就一直被廣泛地研究。時至今日可撓式軟性元件電子書、電子紙張等可捲式數位顯示器的發展，更提供有機分子在半導體方面應用的可能性。在目前的半導體材料中五環素衍生物已可達非晶相無機矽半導體電性表現，然而五環素由於溶解度不佳、純化困難等因素限制其在元件製程上的應用。為了改善這些問題，本研究以萘及蒽為分子單體設計出一系列之二聚物衍生物，藉以改善溶解度、結晶性質、熱穩定性等分子特性，同時在主體末端導入芳香取代基，期望利用這些芳香取代基提高分子的結晶特性以達到好的電荷傳遞特性。在合成方法的設計中，本研究將利用Diels-Alder 反應簡化傳統合成多環芳香烴衍生物的反應步驟並提高材料的產率，此外也可將多環芳香烴分子之位置選擇性增加。從合成過程中本計畫試著合成不同的二苯炔結構的前驅物，前驅物將根據不同之取代基改變反應所需之溫度與試劑以達到合成出二苯炔分子，再利用具有雙烯相似物(diene)之取代基，進行Diels-Alder [2+4]反應合成出一系列有機電晶體。對於本研究所開發之多環芳香烴，在薄膜電晶體方面的應用評估本研究利用UV吸收及FL 放射光譜等瞭解分子的光學特性、利用TGA 及DSC 測量螢光分子的熱穩定性以及材料的形態穩定等特性，同時利用循環電位儀(CV)測量螢光分子的電化學性質以及HOMO/LUMO 能階。研究結果顯示這類電晶體其共振長度增加時，將產生明顯的紅位移現象。另外，在材料的熱性質方面，這些電晶體材料於350℃的範圍內並無明顯的型態變化，且其熱裂解溫度可達450℃左右(C1 及C2)，顯現這類導電分子具有良好的熱穩定性。而經由電化學性質，此系列電晶體材料具有電洞傳遞特性，配合UV光譜的能階計算可知這些材料的HOMO 能階座落在5.65~5.85 eV，而LUMO能階則座落在2.1~2.8 eV。除了材料的合成外，本研究也利用化學計算方式探討材料之HOMO/LUMO 能階時其電子雲分佈情形，由結果顯示當分子於HOMO 能階時，電子雲將集中分子中心，而當LUMO 能階時，則電子雲將移動至雙聚單體之中心萘結構上，顯示此類材料應用於電晶體時，其主要傳遞電荷將是以中心多環芳香烴為主要路徑，其外圍芳香環不參與電荷的傳遞。綜合以上結果此系列之有機分子在電晶體材料的應用應是深具潛力。 Organic molecules have been giving the impression that the insulation material, butsince Professor Hideki Shirakawa discovered conjugated organic molecules can also beconductive, the organic semiconductor materials have been widely studied. The organcicsemiconductor material of pentacene derivatives have excellent electrical performance.However, poor solubility and stability of pentacene limit its application on the fabricationprocess. In this study, naphthalene and anthracene monomer for the molecular design of aseries of ployacenes to improve solubility, crystalline properties, thermal stability, while inthe main terminal to import aryl that could improve the crystallization of molecules inorder to achieve good charge transfer characteristics. These organic transistors weresynthesized by means of Diels-Alder reaction.In the synthetic methods, this study will use the Diels-Alder reaction replace thetraditional synthesis of polycyclic aromatic derivatives. The reason is Diels-Alder reactioncould simplify reaction steps and improve the material yield, the addition that couldincrease reactive selectivity. In this work, according to different substituents an reactiveconduction to choice different bisbenzyne precursors to achieve the synthesis ofbisbenzyne, then using different dienophile substituents will be synthesized a series oforganic transistors.The OTFT application potential of the transistor molecules was assessed from thephotopysical properties, thermal stabilities and electrochemical behaviors. Photophysicalproperties of the fluorophors were characterized from UV-visible and Fluorescence spectra.Thermal properties of the pyrrole fluorophores were investigated by differential scanningcalorimetry (DSC) and thermogravimetric analysis (TGA). Cyclic voltammetry (CV) wasemployed to investigate the electrochemical behaviors of these transistors. The resultsshow that this type of transistor, the resonant length increases, the absorption and emissionwavelength will have obvious red shift. In addition, thermal properties, these transistors C1and C2 there were no obvious morphological change at 350 ℃, and the thermaldecomposition temperature were up to 450 ℃. These result exhibits these transistorspossess highly thermal stability. From the result of redox, these transistors have a holetransmission characteristics. HOMO levels of these transistors were estimated to be around5.65~5.85eV, and the LUMO level were estimated to be around 2.1~ 2.8 eV.In this work, relationship between the chemical architecture and their electroopticalproperties was also studied. In the HOMO level, the electron cloud will focus on molecularcenter, but when the LUMO level, then the electron cloud will distributed to the main partof binaphthalene or bianthracene, indicating that such material used in transistors, thecharge would move from one molecule’s center hopping to another’s molecule’s center, itsmain delivery centers charge will be based on polycyclic aromatic hydrocarbons as themain path, the outer ring is not aromatic participate in charge transfer.

雙苯炔衍生物的合成及其場效電晶體應用 = Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application
吳, 昭霖

雙苯炔衍生物的合成及其場效電晶體應用 = Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application / 吳昭霖撰 - [高雄市] : 撰者, 民99[2010]. - 146面 ; 圖，表 ; 30公分.
參考書目：面.
二苯炔bisbenzyne

雙苯炔衍生物的合成及其場效電晶體應用 = Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application
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330 $a 有機分子一直給人的印象是絕緣的物質，但自從白川英樹教授發現共軛有機分子也可以導電後，有機半導體材料就一直被廣泛地研究。時至今日可撓式軟性元件電子書、電子紙張等可捲式數位顯示器的發展，更提供有機分子在半導體方面應用的可能性。在目前的半導體材料中五環素衍生物已可達非晶相無機矽半導體電性表現，然而五環素由於溶解度不佳、純化困難等因素限制其在元件製程上的應用。為了改善這些問題，本研究以萘及蒽為分子單體設計出一系列之二聚物衍生物，藉以改善溶解度、結晶性質、熱穩定性等分子特性，同時在主體末端導入芳香取代基，期望利用這些芳香取代基提高分子的結晶特性以達到好的電荷傳遞特性。在合成方法的設計中，本研究將利用Diels-Alder 反應簡化傳統合成多環芳香烴衍生物的反應步驟並提高材料的產率，此外也可將多環芳香烴分子之位置選擇性增加。從合成過程中本計畫試著合成不同的二苯炔結構的前驅物，前驅物將根據不同之取代基改變反應所需之溫度與試劑以達到合成出二苯炔分子，再利用具有雙烯相似物(diene)之取代基，進行Diels-Alder [2+4]反應合成出一系列有機電晶體。對於本研究所開發之多環芳香烴，在薄膜電晶體方面的應用評估本研究利用UV吸收及FL 放射光譜等瞭解分子的光學特性、利用TGA 及DSC 測量螢光分子的熱穩定性以及材料的形態穩定等特性，同時利用循環電位儀(CV)測量螢光分子的電化學性質以及HOMO/LUMO 能階。研究結果顯示這類電晶體其共振長度增加時，將產生明顯的紅位移現象。另外，在材料的熱性質方面，這些電晶體材料於350℃的範圍內並無明顯的型態變化，且其熱裂解溫度可達450℃左右(C1 及C2)，顯現這類導電分子具有良好的熱穩定性。而經由電化學性質，此系列電晶體材料具有電洞傳遞特性，配合UV光譜的能階計算可知這些材料的HOMO 能階座落在5.65~5.85 eV，而LUMO能階則座落在2.1~2.8 eV。除了材料的合成外，本研究也利用化學計算方式探討材料之HOMO/LUMO 能階時其電子雲分佈情形，由結果顯示當分子於HOMO 能階時，電子雲將集中分子中心，而當LUMO 能階時，則電子雲將移動至雙聚單體之中心萘結構上，顯示此類材料應用於電晶體時，其主要傳遞電荷將是以中心多環芳香烴為主要路徑，其外圍芳香環不參與電荷的傳遞。綜合以上結果此系列之有機分子在電晶體材料的應用應是深具潛力。 Organic molecules have been giving the impression that the insulation material, butsince Professor Hideki Shirakawa discovered conjugated organic molecules can also beconductive, the organic semiconductor materials have been widely studied. The organcicsemiconductor material of pentacene derivatives have excellent electrical performance.However, poor solubility and stability of pentacene limit its application on the fabricationprocess. In this study, naphthalene and anthracene monomer for the molecular design of aseries of ployacenes to improve solubility, crystalline properties, thermal stability, while inthe main terminal to import aryl that could improve the crystallization of molecules inorder to achieve good charge transfer characteristics. These organic transistors weresynthesized by means of Diels-Alder reaction.In the synthetic methods, this study will use the Diels-Alder reaction replace thetraditional synthesis of polycyclic aromatic derivatives. The reason is Diels-Alder reactioncould simplify reaction steps and improve the material yield, the addition that couldincrease reactive selectivity. In this work, according to different substituents an reactiveconduction to choice different bisbenzyne precursors to achieve the synthesis ofbisbenzyne, then using different dienophile substituents will be synthesized a series oforganic transistors.The OTFT application potential of the transistor molecules was assessed from thephotopysical properties, thermal stabilities and electrochemical behaviors. Photophysicalproperties of the fluorophors were characterized from UV-visible and Fluorescence spectra.Thermal properties of the pyrrole fluorophores were investigated by differential scanningcalorimetry (DSC) and thermogravimetric analysis (TGA). Cyclic voltammetry (CV) wasemployed to investigate the electrochemical behaviors of these transistors. The resultsshow that this type of transistor, the resonant length increases, the absorption and emissionwavelength will have obvious red shift. In addition, thermal properties, these transistors C1and C2 there were no obvious morphological change at 350 ℃, and the thermaldecomposition temperature were up to 450 ℃. These result exhibits these transistorspossess highly thermal stability. From the result of redox, these transistors have a holetransmission characteristics. HOMO levels of these transistors were estimated to be around5.65~5.85eV, and the LUMO level were estimated to be around 2.1~ 2.8 eV.In this work, relationship between the chemical architecture and their electroopticalproperties was also studied. In the HOMO level, the electron cloud will focus on molecularcenter, but when the LUMO level, then the electron cloud will distributed to the main partof binaphthalene or bianthracene, indicating that such material used in transistors, thecharge would move from one molecule’s center hopping to another’s molecule’s center, itsmain delivery centers charge will be based on polycyclic aromatic hydrocarbons as themain path, the outer ring is not aromatic participate in charge transfer.
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