具有三氟甲基或甲基取代之三苯胺成分的新型芳香族聚醯胺及聚醯亞胺之合成與光電性質研究

Synthesis and Optoelectronic Properties of Novel Aromatic Polyamides and Polyimides Bearing Trifluoromethyl- or Methyl-Substituted Triphenylamine Moieties

林楷翰(Kai-Han Lin)

指導教授 ： 蕭勝輝

大同大學/工程學院/化學工程學系所/碩士(2005年)

摘要

兩種含三苯胺結構的二胺單體4,4’-diamino-4”-trifluoromethyltriphenylamine和 4,4’-diamino-4”-methylltriphenylamine是由1-fluoro-4-nitrobenzene 和 4-trifluoromethylaniline 或 p-toluidine進行CsF-芳香親核置換反應，生成二硝化合物後，再以聯胺和Pd/C催化還原反應而得到。具有三氟甲基或甲基取代的三苯胺基團的芳香族聚醯胺及聚醯亞胺係由這二種二胺單體與芳香族二羧酸及二酐聚縮合而得。藉由X-ray繞射測定，所有的高分子均屬非晶型的材質。大部分的高分子在許多有機溶劑中顯示好的溶解性，並可由它們的溶液鑄成透明及強韌的薄膜，他們亦具有高的玻璃轉換溫度和軟化溫度，好的熱穩定性及適當的HOMO能階值。此外電洞傳輸及電致變色的特性也由電化學及光譜電化學的方法來探討。

關鍵字

聚醯亞胺 ； 聚醯胺 ； 三苯胺

並列摘要

Two triphenylamine-containing diamine monomers, 4,4’-diamino-4”-trifluoromethyltriphenylamine and 4,4’-diamino-4”-methyltriphenylamine were synthesized via the cesium fluoride-mediated N-arylation reactions of 4-trifluoromethylaniline and p-toluidine, respectively, with 1-fluoro-4-nitrobenzene, followed by palladium-catalyzed hydrazine reduction of the resulting dinitro triphenylamines. Novel aromatic polyamides and polyimides with trifluoromethyl- or methyl-substituted triphenylamine units were prepared by polycondensation reaction of these two diamine monomers with commercially available aromatic dicarboxylic acids and dianhydrides. All the polymers were amorphous in nature, as evidenced by X-ray diffractograms. Most of them were quite soluble in a variety of organic solvents and could be solution-cast into transparent, tough, and flexible films with good mechanical properties. They also showed high Tg or Ts values, good thermal stability, mechanical properties, and proper HOMO energy levels. Besides, the hole-transporting and electrochromic properties were also examined by electrochemical and spectroelectrochemical methods.

並列關鍵字

polyamide ； polyimide ； triphenylamine

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