Synthesis And Properties Of Polyaryltriphenylamines

Organic small molecule fluorescent materials have become a hot research topic of optoelectronic materials due to their unique hole-transport properties,electron transport properties and bipolar transport properties.Triphenylamine derivatives as the organic small molecule compounds exhibited good application prospect in optoelectronic materials because of their effective hole-transport properties.In this paper,four kinds of multi aryl compounds with triphenylamine motifs were designed by quantum chemistry calculation and synthesized.The properties of these compounds were tested and studied.Three kinds of multi aryl compounds with a highly symmetrical bistriphenylamine group by using benzene,naphthalene and anthracene as the bridging groups were designed and synthesized.Firstly,1,4-dibromobenzene,1,4-dibromonaphthalene and 9,10-dibromoanthracene were respectively used as the starting materials to react with triphenylamine boronic acid by the Suzuki reaction to get intermediates with symmetrical bistriphenylaniline structure.Then the intermediates were brominated by using NBS to obtain tetrabromo intermediates.Finally,the multi aryl compounds with symmetrical bistriphenylaniline structure were obtained by Suzuki coupling reaction with different aryl boronic acids.Wherein,the three kinds of target products were obtained with five compounds,respectively.The structures of target products were confirmed by IR,NMR and HRSM.The thermal properties,photophysical properties and electrochemical properties of the target compounds were tested by TGA,UV,PL and CV.The experimental results indicated that these target products exhibited good solubility,high thermal stability and good hole transport capacity.These compounds showed the potential to be used as hole transport materials.In addition,the products with naphthalene as the bridging group also showed a stable blue light emission and could be used as good fluorescent materials.For the products with anthracene as the bridging group,the HOMO-LUMO energy gaps are about 4 eV,and such wide energy gaps are in favour of the sub-carrier injection and transport.Another kind of multi aryl compOounds by using indolo[3,2-b]indole as the bridging grOoup was designed and synthesized.The N-butylation of indolo[3,2-b]indole was achieved by the alkylation reaction to improve the solubility of the products.The intermediates were prepared by bromination.Multi aryl indoIo[3,2-b]indole derivatives were obtained through the Suzuki coupling reaction with different aryl boronic acid.The structures of these compounds were confirmed by IR,NMR and HRSM.The properties of the target compounds were tested by using TGA,UV,PL and CV.The results indicated that these compounds exhibited high Td values and efficiency hole transport capacity.These compounds could also be used as good photoelectric materials.