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首页> 外文期刊>Chemistry: A European journal >Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes
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Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes

机译：可溶性黄酮类衍生物：合成，表征及其在有机发光二极管中的应用

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摘要

Simple modification of benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine-8,16-dione, an old and almost-forgotten vat dye, by reduction of its carbonyl groups and subsequent O-alkylation, yields solution-processable, electroactive, conjugated compounds of the periazaacene type, suitable for the use in organic electronics. Their electrochemically determined ionization potential and electron affinity of about 5.2 and -3.2 eV, respectively, are essentially independent of the length of the alkoxyl substituent and in good agreement with DFT calculations. The crystal structure of 8,16-dioctyloxybenzo[h]benz[5,6] cridino[2,1,9,8-klmna]acridine (FC-8), the most promising compound, was solved. It crystallizes in space group P (1) over bar and forms pi-stacked columns held together in the 3D structure by dispersion forces, mainly between interdigitated alkyl chains. Molecules of FC-8 have a strong tendency to self-organize in monolayers deposited on a highly oriented pyrolytic graphite surface, as observed by STM. 8,16-Dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines are highly luminescent, and all have photoluminescence quantum yields of about 80%. They show efficient electroluminescence, and can be used as guest molecules with a 4,4'-bis(N-carbazolyl)-1,1'-biphenyl host in guest/host-type organic light-emitting diodes. The best fabricated diodes showed a luminance of about 1900 cdm(-12), a luminance efficiency of about 3 cdA(-1), and external quantum efficiencies exceeding 0.9 %.
机译：通过还原其羰基及随后的修饰，简单改性苯并[h]苯[5,6] ac啶[2,1,9,8-klmna] ac啶-8,16-二酮（一种古老且几乎被遗忘的还原染料） O-烷基化产生适合于有机电子学使用的可进行水溶处理的环紫并苯类型的电活性共轭化合物。它们的电化学测定电离电势和电子亲和力分别约为5.2和-3.2 eV，基本上与烷氧基取代基的长度无关，并且与DFT计算非常吻合。解决了最有前途的化合物8,16-二辛氧基苯并[h]苯[5,6] 6 [2,1,9,8-8啶]（FC-8）的晶体结构。它在棒上的空间群P（1）中结晶，并通过弥散力（主要是在相互交叉的烷基链之间）形成在3D结构中保持在一起的pi堆积柱。 STM观察到，FC-8分子在沉积在高度定向的热解石墨表面上的单层膜中具有很强的自组织趋势。 8,16-二烷氧基苯并[h]苯并[5,6] ac啶[2,1,9,8-klmna] idine啶是高度发光的，并且全部具有约80％的光致发光量子产率。它们显示出有效的电致发光，并且可以与客体/主体型有机发光二极管中的4,4'-双（N-咔唑基）-1,1'-联苯主体一起用作客体分子。制作效果最好的二极管的亮度约为1900 cdm（-12），亮度效率约为3 cdA（-1），外部量子效率超过0.9％。

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