Synthesis and Application of Dimeric 1,3,5-Triazine Ethers as Hole-Blocking Materials in Electroluminescent Devices

A series of low molecular weight dimeric 1,3,5-triazine ethers with high glass transition temperatures is synthesized from 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine and various bisphenols. The thermal and electrochemical properties of these materials are examined using differential scanning calorimetry and cyclic voltammetry, respectively. The glass transition temperatures (Tg) are in the range of 106−144 °C, and all of them have similar thermal stability and show no weight loss up to 380 °C in thermogravimetric measurements. Some of these dimers form stable glasses which do not recrystallize on annealing at or above the Tg. Cyclic voltammetry studies reveal that these compounds undergo reversible reduction between −2.09 and −2.27 V vs ferrocene/ferrocenium as internal standard which correspond to LUMO values between −2.5 and −2.7 eV, respectively. The application of one of these dimeric ethers as a hole-blocking/electron-transport material in organic light-emitting devices is demonstrated.