二苯乙烯二胺分子與Pentiptycene-乙炔寡聚物的合成與物理性質之研究; The Synthesis and Physical Properties of Diaminostilbenes and Pentiptycene-ethynylene Oligomers

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题名:	二苯乙烯二胺分子與Pentiptycene-乙炔寡聚物的合成與物理性質之研究;The Synthesis and Physical Properties of Diaminostilbenes and Pentiptycene-ethynylene Oligomers
作者:	顏巨倫;Chu-Lun Yen
贡献者:	化學研究所
关键词:	二苯乙烯二胺;電致發光;光激發光;化學感應器;quantum yields;Pentiptycene;OLED
日期:	2004-07-08
上传时间:	2009-09-22 10:11:58 (UTC+8)
出版者:	國立中央大學圖書館
摘要:	中文摘要本論文主要以合成非平面性共軛分子以作為有機發光材料之應用。我們首先合成系列一化合物1-A、1-B與1-C，以確定此類二苯乙烯二胺分子在有機溶劑中具有高螢光量產率(如在THF中為0.55~0.76)，於是透過結構上的修飾引入立體性大的triptycene基團，而設計出系列二化合物。系列二化合物在二氯甲烷中的發光範圍為429~441 nm，熱裂解溫度介於325~375℃，玻璃轉移溫度介於80~120℃，HOMO能階介於5.00~5.17，LUMO能階介於1.98~2.22。其中以化合物2-C(441 nm)的光色最接近藍光且熱穩定性最佳，此外，化合物2-C的能階最能搭配陽極(ITO)與電子傳輸層(TPBI)，推測合適的元件結構為ITO/ NPB/ 2-C/ TPBI/ Mg:Ag。另外，我們亦藉由乙炔基將pentiptycene串聯起來而設計出系列三化合物，同樣利用其非平面性以期在固態中仍具高螢光量子產率。在合成系列三化合物中，由於pentiptycene本身立體因素的影響，故合成條件控制較嚴苛，包括正丁基鋰的當量數、反應時間和溫度、還原劑的選擇皆會影響產率，目前已合成3-A與3-B，未來將找尋最佳條件合成3-C與3-D。 Abstract This thesis reports the synthesis of a few nonplanar conjugated molecules as organic light-emitting materials. We first synthesized diaminostilbenes 1-A, 1-B, and 1-C to ensure that these fluorophores would have high fluorescence quantum yields in organic solvents. We then introduce the bulky triptycene group to these diaminostilbenes to form the compound series II (2-A, 2-B, and 2-C). The fluorescence maxima in dichloromethane, decomposition temperatures, glass transition temperatures, the HOMO energies, and the LUMO energies of compounds 2 are in the range of 429-441 nm, 325-375 oC, 80-120 oC, 5.00-5.17 eV, and 1.98-2.22 eV, respectively. Among the three compounds, 2-C has the best physical properties as a blue emitter, and a reasonable OLED device structure for such a purpose would be ITO/NPB/2-C/TPBI/Mg:Ag, where NPB and TPBI are hole and electron transporting materials, respectively. We also have designed a series of pentiptycene-ethynylene oligomers (compound series III) on the basis of the known feature that the nonplanar pentiptycene-incorporated poly(phenylene ethynylene)s can maintain a high fluorescence quantum yields in the solid state. However, the bulky pentiptycene group complicates the synthesis, which requires a subtle control of the reaction conditions, including the amount of butyl lithium, reaction time and temperature, and the choice of reducing reagents. We have currently synthesized 3-A and 3-B, and will find the optimum conditions to prepare oligomers 3-C and 3-D.
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