Study on the Synthesis and Properties of Diphenoquinone Electronic Transporting Materials
|Keywords||Electron transport material Diphenoquinone Synthesis Optical Performance|
Diphenoquinone compounds are an important class of electron transport materials, electron transport with a stable performance, excellent sensitivity, low dark decay potential and good durability and reproducibility, but the poor solubility of existing varieties and with Resin poor compatibility shortcomings limit the practical application of the material, while the synthesis process is not yet mature product, the yield is low, you can not achieve large-scale production. Research and development of this thesis 3,5 - dimethyl-3 ', 5'-di-t-butyl-biphenyl-quinone and 3 - chloro-3', 5,5 '- tri-tert-butyl biphenyl two kinds of diphenoquinone quinone-type electron transport material synthesis process for 3,3 ', 5,5' - tetramethyl diphenoquinone amplify the synthesis process was studied, and the optical properties of materials were tested and compared. Studied the feeding method, the reaction time, reaction temperature, etc. of the material ratio of 2,6 - dimethyl phenol and 2,6 - di-tert-butylphenol oxidative coupling reaction of 3,5 - dimethyl-3 ', 5 '- di-tert-butyl biphenyl quinone, and identifies the optimum synthesis conditions: two materials mixed in chloroform was added dropwise time was 2h, the reaction temperature is 50 ℃, the reaction time was 4h, potassium permanganate the two reactants and the molar ratio of 8:1:1. Product HPLC purity 99.53%, 48.99% yield. Explore the 3,3 ', 5,5' - tetra-t-butyl-biphenyl-quinone reaction of the de tert-butyl chloride Preparation of 2 - chloro-2 ', 6,6' - tri-tert-biphenol, via oxidation Synthesis of 3 - chloro-3 ', 5,5' - tri-tert diphenoquinone process route, the system studied and de-tert-butyl chloride oxidation factors. De-t-butyl-chloro determined optimal reaction conditions were: the protection of nitrogen was passed through the HCl gas, an amount of carbon tetrachloride solvent, 25mL / g raw material, the aluminum trichloride catalyst molar ratio of the reactants is 0.77: 1, the reaction time was 10h, the reaction temperature is 15 ~ 20 ℃. Optimum conditions for the oxidation reaction: solvent chloroform dosage 50 mL / g raw material, lead dioxide oxidant and reactant molar ratio of 20:1, the reaction temperature is 50 ℃, reaction time was 3h. Two-step reaction product yields were 62.47% and 84.02%, HPLC purity products were 90.80% and 99.13%, by melting point, IR, MS and NMR analysis of the structure is correct. Of 2,6 - dimethyl phenol synthesis of 3,3 ', 5,5' - tetramethyl biphenyl quinone amplification process was studied in 1L reaction flask, 0.30mol material, 1.5mol high potassium, 0.45L chloroform as solvent, reaction temperature 55 ℃, reaction time 8h conditions, the yield of product was 90.78%, 99.42% purity, to achieve the size of each batch preparation of 32.68g. Of 3,5 - dimethyl-3 ', 5'-di-tert-butyl biphenyl quinone 3 - chloro-3', 5,5 '- tri-tert-butyl biphenyl hydroquinone, 3,3', 5, 5'-tetramethyl biphenyl quinone and 3,3 ', 5,5' - tetra-tert-butyl biphenyl quinone four materials optical properties were studied and compared. The results show that 3,5 - dimethyl-3 ', 5'-di-t-butyl-biphenyl-quinone and 3 - chloro-3', 5,5 '- tri-tert-butyl biphenyl compounds with resin has good compatibility, the charging potential is high, the residual potential is low, has good photosensitivity.