新型含噻吩基8-羟基喹啉锌配合物的合成及光电性能

Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group

设计合成了含噻吩基的新型配体(E)-2-[2-(3-噻吩基)乙烯基]-8-羟基喹啉(4)及相应的锌配合物5,产物结构经核磁共振、红外光谱和元素分析进行表征.利用X射线单晶衍射仪测定了中间体(E)-2-[2-(3-噻吩基)乙烯基]-8-乙酰氧基喹啉(3)和配体4的单晶结构,结果表明中间体3晶体分子间并无明显的氢键作用,分子间呈交错堆叠;配体4分子之间由硫氢氧键弱作用相互排列形成网状结构.通过核磁滴定及紫外和荧光滴定模拟了配体4在溶液中与金属锌的配位过程.固体荧光寿命研究结果表明,配合物5的荧光寿命为18.8 ms.通过电致发光器件研究发现,配合物5作为发光层具有良好的电致发光性能,同时具有较好的电子传输能力.

8-Hydroxyquinoline has long been employed as analytical and separating agents due to its universal chelating ability offered by the heterocychc N and phenolate O atoms and fluorescent property possessed by the conjugate system. In order to increase its fluorescence capability and conjugate system, 3-thiophene has been added. A novel 8-hydroxyquinoline derivative ligand containing thiophene group （E） -2-[ 2-（ 3-thiophenyl ） ethenyl]-8-hydroxyquinoline（4） and its corresponding zinc complex （5） were synthesized and identified via 1H NMR, FTIR, UV-Vis, X-ray structural analysis and elemental analyses. The crystal structures of interme- diate （E） -2- [ 2- （ 3-thiophenyl ） ethenyl ] -8-acetoxyquinoline （ 3 ） and ligand 4 were characterized by single- crystal X-ray diffraction. X-Ray structural analysis showed that there was no obvious hydrogen-bonding interac- tion between the molecules of compound 3. The crystal reticular structure of compound 4 was constructed as a result of intermolecular O--H＇--S hydrogen bonds. The aggregation behaviors of zinc salts and compound 4 in solutions were investigated with a variety of techniques, including I H NMR, UV-Vis and fluorescence. The fluorescence lifetime of complex S was determined in the solid state and its r value is 18.8 ms. Organic light- emitting diodes built using complex $ emitted yellow light, in which the 1,3,5-tris（ 1-phenyl-lH-benzimidazol- 2-yl） benzene（TPBi） acts as the electronic transmission layer, while N, N＇-bis-（1-naphthalenyl）-N, N＇-bis- phenyl- （ 1, l＇-biphenyl） -4,4＇-diamine （ NPB ） acts as hole transport material.