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  • 學位論文

喹喔啉衍生物的有機發光二極體材料之合成與性質研究

Quinoxaline Derivatives of Organic Light-Emitting Devices Materials:Synthesis and Properties

指導教授 : 段葉芳
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摘要


本研究利用Diketone及Diamine脫水縮合反應製備十二種Quinoxaline衍生物,並以NMR及IR鑑定其結構,再以UV-Vis及PL測其光學性質、TGA及DSC測其熱性質,探討改變材料的化學結構及導入不同的官能基對於光學性質及熱性質的影響。   利用UV-Vis及PL測量化合物的光物理性質,發現化合物導入溴原子與甲 基後,皆有些許的紅位移;導入苯環,增加化合物的非定域性分子軌域,則會產生較大的紅位移現象。尤其是在不同位置導入二個苯環,增加平面分子的剛性並形成多環結構,共振延伸的效應,使得化合物π*軌域的能量降低,產生極明顯的紅位移,最具代表性的化合物為Tribenzo[a,c,i]phenazine (Q2),其最大吸收峰發生在312nm處,其餘十一種quinoxaline衍生物的最大吸收峰則分佈在242 nm∼278nm間。   此外,喹喔啉(Quinoxaline)衍生物在相同濃度溶於不同溶劑中以UV光致發光,各組以2號系列化合物發光顏色最為明顯,發光顏色明顯紅位移至綠色。   以TGA及DSC測量化合物的熔點及5%裂解溫度,發現化合物的熔點及裂解溫度皆會隨著導入的不同官能基而增加,其中以具有多環芳香環的化合物熱性質最為良好。實驗結果顯示,改變quinoxaline衍生物的化學結構,確實可增強其傳導電子能力,使熱性質更穩定,適合用來當作電子傳輸層材料及發光材料,更可用來當作綠光的摻雜物,是個非常實用的化合物。

並列摘要


The purpose of this study is to synthesize twelve kinds of quinoxaline derivatives by the dehydration condensation reaction using diketone and diamine materials,their structures were identified by NMR and IR, optical properties were measured by UV-Vis and PL, thermal properties were measured by TGA and DSC, to investigate the effects of changing the chemical structure and different functional groups on the optical properties and thermal properties .The results are divided into three parts as follows: (1) The optical properties of compounds were measureed by UV-Vis and PL, there are a slight red shift when compounds is imported into bromine and methyl. When the compound's nonlocality molecular orbitals increases, a greater red shift will appear . The most representative of these compounds is tribenzo[a,c,i]phenazine(Q2),the maximum absorption peak appears at 312nm,while other eleven derivatives appear the maximum absorption peak between 242 nm∼278nm. (2) The measurements by TGA and DSC, the melting point and 5% degradation temperature of the compound both increase as different functional groups added into compound, especially when the number of derivatives benzene rings increase, the compound has the most good thermal properties. (3) Experimental results indicate that changing the chemical structure of quinoxaline derivatives indeedly enhance the electron transporting ability,make a more stable thermal properties, be suitable for the electron transport layer material and as a light emitting material, even can be used as a green dopant , this quinoxaline derivatives are very useful compounds.

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