| 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. |
