本研究以單體4,4’’’’-Difluore-3,3’’’’-bis(trifluoromethyl)-2’’,3’’,5’’,6’’-triphenyl (M4)經由親核性取代反應與雙酚單體A1、A2、B1、B2產生新穎聚芳香醚高分子，所生成聚合物我們命名為P-A1、P-A2、P-B1、P-B2。使用Mass、GPC鑑定其分子量；NMR、FT-IR對其分子結構鑑定分析，證明所生成之聚合物為本研究所指的聚芳香醚高分子。此一系列的聚芳香醚高分子具有較高的轉化率和高分子量(Mn：2.2×10^4 ~ 2.2×10^5 g/mol)。從聚芳香醚高分子的熱穩定性測量中可知，其裂解溫度(Td5%)在450°C ~ 548°C，而玻璃轉移溫度(Tg)為303°C ~ 324°C，顯示聚芳香醚高分子擁有很好的熱穩定性；此外這些高分子並無明顯的結晶點(Tc)，所以可推斷本研究之聚芳香醚高分子不易結晶。由此可知本研究之聚芳香醚高分子不僅耐熱性佳且熱穩定性高，因此更能接受較高溫度的製程。在薄膜光學特性方面，高分子薄膜的吸收波長232nm ~ 300nm，而放光波長為362nm ~ 368nm；且高分子P-A1、P-A2的可見光穿透率在91%以上，高分子P-B1、P-B2的可見光穿透率在83%以上。而高分子薄膜的折射率(n)介在1.33 ~ 1.49之間。在疏水性量測中發現高分子薄膜與水的接觸角都大於109.8°，所以此系列高分子薄膜的疏水性佳。綜合以上諸點的實驗結果，可知此系列聚芳香醚高分子在具有良好的熱穩定性、高可見光穿透度且疏水性佳。由於這些良好的材料特性，使得此系列聚芳香醚高分子未來適合用來做為光電元件軟性基板的材料。

Monomer 4,4’’’’-Difluore-3,3’’’’-bis(trifluoromethyl)-2’’,3’’,5’’,6’’-triphenyl (M4) were converted to novel poly(arylene ether)s by nucleophilic displacement reaction with several bisphenols in this study, then we called them : P-A1, P-A2, P-B1, P-B2. These polymers exhibit weightaverage molecular weight (Mw) between 2.2×10^4 to 2.2×10^5 g/mol. The molecular weight were investigated and confirmed by Mass and GPC. The molecular structures were investigated and confirmed by NMR and FT-IR.Thermal analysis physics studies with these polymers confirmed by Thermogravimetric analyzer (TGA) and differential scanning calorimetry (DSC). It is indicated that Td 5% of these polymers were 450°C ~ 548°C in TGA and Tg of these polymers were 303°C ~ 324°C in DSC.Besides, these polymers not were observed apparent crystallizing point, so we consider that they are not easy crystallized. Therefore, they could make manufacture in higher temperature and have higher thermal stability.In photophysical property of polymeric thin films, we obtained absorption wavelength that was 232nm ~ 300nm in UV-Vis absorption spectra and excitation wavelength that was 362nm ~ 368nm in PL spectra. Furthermore, the transmission spectra of polymeric thin films showed that visible light transparency were up to 83%. Besides, we used Ellipsometer to measure refractive index(n) that is 1.33 ~ 1.49.In drop shape analysis system, contact angles of the polymeric thin films are more than 109.8°. They show that the polymer thin films have low polarity and good hydrophobicity. By above material properties of these polymers, they have high thermal stabilities, high optical transparency, low polarity and good hydrophobicity. These good material properties are doing as a plastic substrate of devices or panel display.

致謝 I
摘要 III
Abstract V
目錄 VI
圖目錄 IX
表目錄 XIII
第一章 緒論 1
1-1 前言 1
1-2 文獻回顧 3
1-3 研究動機 5
第二章 實驗儀器與藥品 7
2-1藥品 7
2-2 儀器 7
2-2-1 傅利葉轉換式質譜儀(Fourier-transfer mass spectrometry，FT-MS spectrometry) 7
2-2-2 凝膠滲透層析儀(Gel Permeation Chromatography，GPC) 9
2-2-3 高磁場液態核磁共振儀(Nuclear magnetic resonance，NMR) 11
2-3-4 傅立葉轉換式紅外光譜儀(Fourier transform infrared spectrometer，FT-IR spectrometer) 12
2-2-5 熱重分析儀(Thermogravimetric analyzer，TGA) 14
2-2-6 熱示差掃描卡量計(Differential scanning calorimetry, DSC) 16
2-2-7 紫外與可見光光譜儀(Ultraviolet and visible spectrometer ，UV-Vis spectrometer) 18
2-2-8 螢光光譜儀(Fluorescence spectrometer) 20
2-2-9 旋轉塗佈機(Spin coater) 22
2-2-10 表面輪廓分析儀(Surface profiler) 23
2-2-11 橢圓偏振光測量儀(Ellipsometry) 25
2-2-12 液滴形狀分析系統(Drop shape analysis system) 26
第三章 材料製備與鑑定 28
3-1 中間體、單體之合成與鑑定 31
3-1-1 1,3-Bis(4-bromophenyl)propan-2-one之合成(反應A)與鑑定 31
3-1-2 2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopenta-2,4-dienon之合成(反應B)與鑑定 37
3-1-3 4,4”-Dibromo-2’,3’,5’,6’- tetraphenyl[1,1’;4’,1”]terpheny之合成(反應C)與鑑定 41
3-1-4 4-fluoro-3-trifluoromethyl phenyl boronic acid之合成(反應D)與鑑定 46
3-1-5 4,4’’’’-Difluore-3,3’’’’-bis(trifluoromethyl)- 2’’,3’’,5’’,6’’ -triphenylru之合成(反應E)與鑑定 52
3-2 高分子聚合物之合成與鑑定 57
3-2-1 高分子P-A1之合成(反應F)與鑑定 57
3-2-2 高分子P-A2之合成(反應G)與鑑定 64
3-2-3 高分子P-B1之合成(反應H)與鑑定 71
3-2-4 高分子P-B2之合成(反應I)與鑑定 78
第四章 材料特性分析與討論 86
4-1材料熱穩定性分析 86
4-2材料光學特性分析 94
4-2-1吸收、放光與穿透光譜分析 94
4-2-2材料光學折射分析 107
4-3材料疏水性分析 110
4-4材料溶解特性 114
第五章 結論 117
5-1結論 117
5-2未來工作 118
參考文獻 119

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