4-苯乙炔-1,8-萘酰亚胺荧光化合物的合成及电致发光性能  

The Studies of Synthesis and Electroluminescence of 4-Phenylethynyl-1,8-Naphthalimides

作　　者：杨建新[1] 文金霞[1] 徐龙鹤[2] 

机构地区：[1]海南大学理工学院海南省精细化工重点实验室,海南海口570228 [2]沈阳化工研究院,辽宁沈阳110021

出　　处：《发光学报》2007年第4期498-504,共7页Chinese Journal of Luminescence

基　　金：海南省自然科学基金(80604);海南省教育厅高校科研基金(Hjkj200702)资助项目

摘　　要：采用Pd(PPh3)2Cl2-CuI为催化剂,Ph3P为配体,4-溴-1,8-萘二酸酐为原料,在乙醇溶液中高收率地合成了4-苯乙炔-1,8-萘酰亚胺和4-对甲基苯乙炔-1,8-萘酰亚胺荧光新化合物。光谱研究表明,它们的最大紫外吸收波长(λUV,max)分别为374,380 nm,最大荧光发射波长(λFL,m ax)分别为446,462 nm,且有较高的荧光量子效率。电致发光性能测试表明,器件的最大发光亮度达到2250 cd/m2,是一类有潜在应用价值的小分子发光材料。1,8-Naphthalimide derivatives are luminophore compounds that are widely used in various fields of science and technology and exhibit all the necessary optical characteristics for polymer materials. And they are readily available from a synthetic point of view. They have been used as fluorescent brightening agents and fluorescent dyes. Furthermore, in recent years many organic luminophores with highly p-conjugated systems on phenylacetylene-based moieties have been developed quickly. The elongated electronic pathways along p-extended conjugations in these molecules often present a bathochromic shift in the absorption and fluorescence spectra. Because of their intriguing electro-conductive, magnetic and optical properties, these compounds can be used as electrical conductors in LED displays, fluorescence sensors, lasers etc. Here, two new 4-phenylethynyl-1,8-Naphthalimide fluorescent compounds which phenylethynyl moietie is conjugated at the 4-position of the naphthalene ring are prepared through Pd（ PPh3 ）2Cl2-catalyzed Sonogashira reaction from 4-bromo-1,8-naphthalimide in ethanol with CuI as co-catalyzer and Ph3P as ligand, and their UV/vis absorption and fluorescence emission spectral properties were studied using prepared solutions in DMF. The respective quantum yields were determined using quinine sulphate as the emission standard. Their electroluminescent characteristics were also determined as a dopped device. Reactions were carried out using 5% bis-[ triphenylphosphine] palladium dichloride as catalyst and 5% CuI as co-catalyst in ethanol at reflux temperature with triethylamine as base. N-alkyl-4-bromo-1,8-naphthalimides were conveniently prepared by the condensation of 4-bromo-1,8- naphthalimides and primary alkylamine in ethanol with good yields. Their structures are characterized using IR, NMR and EA. The absorptionemission spectra and fluorescence quantum yields are determined and the relationships between molecular structure and fluorescence properties are studied. It is shown from the absor

关 键 词：1 8-萘酰亚胺 苯乙炔 电致发光 

分 类 号：TQ628.2[化学工程—精细化工]