Synthesis Of Novel Holetransport Materials Containing Triarylamine And Its Properties

Hole-transporting material is one of the most important components forphotoelectric devices. The ideal HTM with excellent hole injection efficient and holemobility, good emission fluorescence spectrum, high thermal stability, which havebeen focused on the organic opto-electronic materials for nearly two decades. Threehole-transport materials containing triphenylamine unit have been designed andsynthesized in this paper, which using ethylenic bond, benzene, triarylamine unit asthe bridge to connect two molecule of triphenylamine, respectively.Hole-transport material (Z)-4,4’-(ethene-1,2-diyl)bis(N,N-dip-tolylbenzenamine)(HTM1) have been synthesized through Mcmurry reaction using4-(di-p-tolylamino)benzaldehyde; Moreover, N,N’-(4,4’-(1E,1’E)-2,2’-(1,4-phenylene)bis(ethene--2,1-diyl)bis(4,1-phenylene))bis(4-methyl-N-p-tolylbenzenamine)(HTM2) and4-((E)--4-(dip-tolylamino)styryl)-N-(4-((E)-4-(dip-tolylamino)styryl)phenyl)-N-p-tolylbenz-enamine (HTM3) have been synthesized by the wittig reaction of4-(di-p-tolylamino)benzaldehyde and terephthalaldehyde or4,4’-(p-tolylazanediyl)dibenzaldehyde,respectively. The structures of compounds have been characterized by theIR, MS and1H NMR.The fluorescence spectrum, thermo-stabilization and electrochemical properties ofthree HTM were studied. The results show that fluorescence emission of compoundexpanding theπ-πconjugate is more red-shift than that of expanding thep-πconjugate. The emission fluorescence spectrum of target compounds are HTM1(415nm)<HTM3(448nm)<HTM2(487nm); The glass transition temperature ofHTM has closely relationship with their molecular weight, followed by HTM1(81.59℃)<HTM2(95.80℃)<HTM3(114.68℃); The values of HOMO energy levelof the compounds are followed by HTM1(-5.53eV)<HTM2(-5.49eV)<HTM3(-5.43eV), all of them will be satisfy the requirement of application.In addition, the optimistic structure and the single point energies were calculated onGaussian03by DFT theory. From the calculation, the geometry, Mulliken charge,dipole, the frontier molecular orbital moment have been obtained.