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研究生： 吳信忠
Hsin_Chung - Wu
論文名稱： 含有Benzo[c]cinnoline結構單元之共軛高分子之合成及其光電性質探討
Synthesis and Optoelectronic Properties of Conjugated Polymers Containing Benzo[c]cinnoline Moieties
指導教授： 陳志堅
Jyh-Chien Chen
口試委員: 劉貴生
Guey-Sheng Liou
蕭勝輝
Sheng-Huei Hsiao
王立義
Lee-Yih Wang
王建隆
Chien-Lung Wang
學位類別： 博士
Doctor
系所名稱： 工程學院 - 材料科學與工程系
Department of Materials Science and Engineering
論文出版年： 2015
畢業學年度： 104
語文別： 英文
論文頁數： 195
中文關鍵詞： 共軛高分子 、含氮雜環 、電化學性質 、施體-受體 、有機場效電晶體 、光致發光 、多電解質
外文關鍵詞： polyoxadiazole, MEH-PPV, donor-acceptor, polyfluorene, heteroaromatic cation
相關次數： 點閱：335  下載：4 
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    • 本研究成功合成主鏈上具有含氮雜環benzo[c]cinnoline之共軛高分子，包含poly(1,3,4-oxadiazole)s (POXD (I) 與 (T))、 poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]s (MEH-PPVs) (P10、P25與P50)以及 polyfluorenes (BF10、BF25與BF50)，並進一步對此些高分子進行表徵。其中，透過對含氮雜環benzo[c]cinnoline之四級胺化，高分子BF50形成多電解質(polyelectrolyte) BF50Br。在poly(1,3,4-oxadiazole)s之研究中，透過循環伏安法(cyclic voltammetry)的量測，POXD (I) 與 (T)發現到兩段的還原峰型。將循環伏安法之結果搭配分子模擬，我們推論出第一段之還原應是oxadiazole單元接受了第一個電子，第二段還原則是benzo[c]cinnoline單元接受了第二個電子。此結果顯示出oxadiazole相對於benzo[c]cinnoline，具有較佳之電子親和力。而MEH-PPV之衍生物P10、P25與 P50被做為半導體層，導入構型為下閘極-上接觸(bottom-gate, top-contact)之有機場效電晶體(organic field-effect transistors, OFETs)，並在空氣環境中進行元件之量測。其中，高分子P10量測到p型材料之特性，即傳導電洞之性質。相對來說，P25與 P50則無法量測到電洞之傳導，但卻展現出n型材料傳導電子之特性。同時，將P50為半導體層之有機場效電晶體在空氣環境下進行30天的保存，其電子傳導率(electron mobility)並沒有顯著之下降，數值仍維持在同一個階乘，展現出良好之穩定性。據我們所知，此研究首先提出具有良好空氣穩定性以及n型材料特性之MEH-PPV衍生物，並證明透過benzo[c]cinnoline單元之導入，可將p型材料MEH-PPV轉換成n型之材料。具有benzo[c]cinnoline單元之polyfluorenes (BF10, BF25, and BF50)則被配置成稀薄溶液，並以352 nm之紫外光(UV)進行照射。照光後可觀察到溶液的光致發光(photoluminescence, PL)強度提升。此現象之原因應為照光後，高分子主鏈上的fluorene單元形成含有氧原子之基團，導致高分子之有效共軛鏈段變短，同時抑制了高分子之施體(donor)與受體(acceptor)間的交互作用力。如將照光後之溶液加入三氟醋酸(trifluoroacetic acid)，則可進一步抑制其溶液之光致發光。此研究最後，透過建立紫外光劑量(UV dose)與光致發光量子效率(PL quantum yields)之線性關係，顯示出此系列材料有應用於感測紫外光強度之潛力。新型之多電解質BF50Br在高極性溶劑DMSO、NMP、甲醇(methanol)與 乙醇(ethanol)中，展現出比BF50更好的溶解度，並在這些溶劑中發出藍光。其中，以NMP作為溶劑之BF50Br溶液，展現出比前驅物BF50更高的的光致發光量子效率以及更純的藍光。透過一系列對於含有benzo[c]cinnoline單元之共軛高分子之研究，顯示出具有benzo[c]cinnoline單元之共軛高分子，皆具有獨特之光電特性。

    The conjugated polymers, including poly(1,3,4-oxadiazole)s (POXD (I) and (T)), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]s (MEH-PPVs) (P10, P25, and P50), and polyfluorenes (BF10, BF25, and BF50) containing benzo[c]cinnoline moieties, were synthesized and characterized. The polyfluorene containing benzo[c]cinnoline moieties, BF50, was further quaternized to obtain the polyelectrolyte, BF50Br. Two reduction peaks were observed for POXD (I) and (T) during cyclic voltammetry (CV) cathodic scan. From CV characterization combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. The bottom-gate, top-contact organic field-effect transistors (OFETs) based on P10, P25, and P50 were performed under ambient conditions. The OFET based on P10 only exhibited p-channel characteristic. In contrast, we could not determine the hole mobilities of P25 and P50. The OFETs of these two polymers only exhibited n-channel characteristics. No significant variation in electron mobility can be observed after P50-based OFET was stored under ambient conditions up to 30 days. To the best of our knowledge, this is the first time that air-stable n-channel MEH-PPV derivatives have ever been reported. It indicated that p-type MEH-PPV can be transformed into n-type materials upon incorporation of benzo[c]cinnoline moieties. By UV irradiation (352 nm), the PL (photoluminescence) intensity of dilute polymer solutions of BF10, BF25, and BF50 was enhanced. The PL emission enhancement was attributed to the shorter conjugated length and the reduced donor-acceptor interaction caused by oxygen-containing groups that were formed on fluorene moieties by UV irradiation. The enhanced emission could be quenched further by the addition of proton donors such as trifluoroacetic acid. The completely alternating polymer BF50 consisting of fluorene and benzo[c]cinnoline moieties in dilute THF solution showed linear relationship between UV doses and PL quantum yields after UV irradiation. It exhibited good potential for UV-sensing applications. The solubility of the polyelectrolyte, BF50Br, in polar solvents including DMSO, NMP, methanol, and ethanol was improved obviously after modification. BF50Br exhibited blue-light emitting at 437 nm in NMP, accompanied with higher quantum yield and narrower FWHM (full width at half maximum) than its precursor polymer. The blue-light emission of BF50Br was also observed in DMSO, methanol, and ethanol. The unique optoelectronic properties have been investigated in a series of researches of various polymers containing benzo[c]cinnoline moieties.

    摘要 I Abstract III Acknowledge V Contents VIII List of Tables XII List of Schemes XIII List of Figures XIV Preface 1 Chapter A: Introduction and Motivation 2 Introduction 3 Organic Conjugated Polymers 3 Electron-Donors 7 Electron-Acceptors 12 Donor-Acceptor Copolymers Containing Dual Acceptors 18 2-Dimensional Donor-Acceptor Copolymers 20 High-Performance Donor-Acceptor Copolymers 23 Benzo[c]cinnoline 26 Motivation 28 Chapter B: Experimental 29 Materials 30 Measurements 31 Synthesis of monomers and polymers 33 4,4’-Dibromo-2,2’-dinitrobiphenyl (1) 33 3,8-Dibromobenzo[c]cinnoline (2) 34 3,8-Dicyanobenzo[c]cinnoline (3) 34 3,8-Benzo[c]cinnolinedicarboxylic acid (4) 35 3,8-Benzo[c]cinnolinedicarbaldehyde (5) 36 Polyhydrazide and Polyoxadiazole Derivatives Containing Benzo[c]cinnoline Moieties (PHA (I), PHA (T), POXD (I), and POXD (T)) 37 MEH-PPV Derivatives Containing Benzo[c]cinnoline Moieties (P10, P25, and P50) 39 Polyfluorene Derivatives Containing Benzo[c]cinnoline Moieties (PFO, BF10, BF25, and BF50) and Model Compound (FBF) 41 Polyelectrolyte Containing Benzo[c]cinnoline Derivative, 2,3-Dihydrobenzo[c]pyrazolo[1,2-a]cinnolium Cation Moieties (BF50Br) 44 Fabrication of devices 45 Electron-Only Devices 45 Organic Field-Effect Transistors 45 Simulation methods 47 PHA (T) and POXD (T) 47 MEH-PPV and P50 47 Chapter C: Investigations on the Electrochemical Properties of New Conjugated Polymers Containing Benzo[c]cinnoline and Oxadiazole Moieties 49 Abstract 50 Introduction 51 RESULTS AND DISCUSSION 54 Physical Properties of PHA (I), PHA (T), POXD (I), and POXD (T) 54 Electrochemical Properties 56 Conclusions 64 Chapter D: Synthesis and Properties of Air-Stable n-Channel Semiconductors Based on MEH-PPV Derivatives Containing Benzo[c]cinnoline Moieties 65 Abstract 66 Introduction 67 Results and Discussion 71 Synthesis of Monomer 71 Synthesis of Polymers 73 Optical Properties 78 Electrochemical Properties 89 Organic Field-Effect Transistor Performance 94 Conclusions 99 Chapter E: UV-Irradiation-Enhanced Photoluminescence Emission of Polyfluorenes Containing Heterocyclic Benzo[c]cinnoline Moieties 100 Abstract 101 Introduction 102 Results and Discussion 105 Synthesis and Characterization 105 Electrochemical Properties 111 Optical Properties 114 UV-Irradiation-Enhanced PL Emission 118 Conclusions 136 Chapter F: Novel Polyelectrolyte Containing Benzo[c]cinnoline Derivative, 2,3-Dihydrobenzo[c]pyrazolo[1,2-a]cinnolium Cation Moieties 137 Abstract 138 Introduction 139 Results and Discussion 142 Synthesis and Characterization 142 Electrochemical Properties 147 Optical Properties 149 Conclusions 156 Chapter G: Conclusions 157 Conclusions 158 Chapter H: References 160 References 161

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