我們成功利用2-hydroxybenzaldehyde, 4-aminotriphenylamine 和paraformaldehyde合成出一新穎含三苯胺官能基之氧代氮代苯并環己烷單體(TPA-Ba)，並利用1H NMR，元素分析 (EA) 和 Fourier Transform Infrared (FTIR) 光譜鑑定其結構。氧代氮代苯并環己烷為一加熱後會行開環反應的官能基，在微掃描卡計(DSC)中，在144 oC 有一吸熱峰為該單體的熔點，在240 oC 有一放熱峰為氧代氮代苯并環己烷之開環反應的溫度。我們亦加熱使TPA-Ba行開環聚合反應得到polybenzoxazine (PTPA-Ba)，利用GPC測得分子量(Mw)為8347，TPA-Ba開環聚合反應係根據mechanism B，而PTPA-Ba為一phenolic type polybenzoxazine。我們使用循環伏特計(CV)探討其電化學行為，我們發現三苯胺會行dimerization並行成tetraphenylbenzidine，我們亦測量其HOMO 和 LUMO能階以探討其應用於電洞傳遞材料(hole transporting material)的潛力。

A novel benzoxazine containing triphenylamine moiety: 3-triphenylamine-3,4-dihydro-2H-1,3-benzoxazine (TPA-Ba) have been synthesized from 2-hydroxybenzaldehyde, 4-aminotriphenylamine and paraformaldehyde. The monomer was characterized by 1H NMR, Elemental Analysis (EA) and Fourier Transform Infrared (FTIR). DSC analysis of the monomer shows two peaks, one is an endothermic peak at 144 °C which corresponds to the melting point of the monomer and an exothermal peak at 240 °C which corresponds to the ring opening process of the benzoxazine ring. The monomer underwent thermal polymerization in order to form polybenzoxazine (PTPA-Ba). The obtained polybenzoxazine have molecular weights of 8347, as measured by GPC. The polymer was characterized by FTIR and 1H NMR. The polymer shows good solubility in common organic solvent and good thermal stability. The ring opening polymerization of benzoxazine ring was investigated and found to be following mechanism B, which resulting the phenolic type polybenzoxazine. Electrochemical study was performed on PTPA-Ba. Electrochemical study of PTPA-Ba shows that electropolymerization can occur on PTPA-Ba. As a result of electropolymerization, thin film will be formed on top of ITO glass surface. The HOMO and LUMO energy levels of PTPA-Ba was measured in order to investigate the potential of PTPA-Ba as hole transporting material.

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