Synthesis Of Diphenoquinone Derivatives And Study On Its Photoconductor Property

Diphenoquinone derivatives have been synthesized by corresponding 2,6-alkyl phenol with potassium hypermanganate in chloroform.The purifying method and its photoconductive property have been also studied in this paper. Using 2,6-di-tert-butyl phenol as raw material, the suitable reaction condition of 3,3′,5,5′-tetratert-butyl-4,4′-diphenoquinone is that reactant concentration is 12.5%, the mole ratio of KMnO4 and reactant is 5:1, reaction temperature is 46 ℃ and the yield is 96.23%. Using 2,6-di-tert-butyl phenol and 2,6-dimethyl phenol as raw material, the suitable reaction condition of 3,5-dimethyl-3′,5′-di-tert-butyl-4,4′-di -phenoquinone (DMDB-1) is that reaction time is 3h, reaction temperature is 52 ℃, the size of KMnO4 is more than 120 items and the yield is 90.01%. Using 2-methyl-6--tert-butyl phenol as raw material, the suitable reaction condition of 3,3′-dimethyl-5,5′-di-tert-butyl-4,4′-diphenoquinone(DMDB-2) is that reaction time is 3.25h, reaction temperature is 51℃, the size of KMnO4 is more than 120 items and the yield is 89.91%. All the compound structure was confirmed by melting point, UV, IR, MS and element analysis. Using the synthesized compound as electron transport material, the positive and bipolar photoconductive property were studied and gotten the following conclusions. The symmetrical diphenoquinone was not suitable for preparing photoconductor. When DMDB-1 and DMDB-2 respectively mixxed with 3,3′,5,5′-tetra-tert-butyl -4,4′-diphenoquinone, the latter mass content was not over 50%, respectively got its photoconductive date as following: V_max=260V,△V=40V,Vr=25V,E_1/2=1.0lx·s; Vmax=524V,△V=20V,Vr=10V,E_1/2=1.0lx·s. The property of photoconductor prepared by non-symmetrical diphenoquinone was also studied. When the ratio of DMDB-1 or DMDB-2 to resin was between 0.4 and 0.6, respectively got its photoconductive date as following: Vmax=340V,?V=20V,Vr=80V,E_1/2=1.6lx·s; Vmax=840V,?V=40V,Vr=180V,E_1/2=2.67lx·s. When using as electron transport material, the photoconductor property of DMDB-2 is superior to DMDB-1. The negative property of photoconductor prepared by non-symmetrical diphenoquinone and m-TPD was excellent with Vmax=650V,△V=50V,Vr=40V,E_1/2=0.8lx·s. But the positive property was worse, Vmax=480V,?V=60V,Vr=130V,E_1/2=13.2lx·s. For bipolar photoconductor, there was no influence of DMDB-1 and DMDB-2 on the hole transport property of m-TPD, While on the other hand, there was negative influence of m-TPD on the electron transport property of DMDB-1 and DMDB-2.