Synthesis And Properties Of Photoelectric Materials Based On Phenanthroimidazole Derivatives

Three series of16kinds novel bipolar phenanthroimidazole derivatives, containingcarbazole structure, phenothiazine structure and thiophene structure, were designed andsynthesized in this thesis. They were characterized by means of1H,13C NMR, FTIR andelemental analysis. The optical, electrochemical and thermal properties were alsoinvestigated.1．Bipolar blue materials containing carbazole structureUsing carbazole and phenanthrenequinone as raw materials, four novel phenanthroim-idazole derivatives wer synthesized:3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-ethyl-carbazole(CP1),3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-butyl-carbaz-ole(CP2),3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-hexyl-carbazole(CP3) and3,6-dis(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-ethyl-carbazole(CP4).All comp-ounds show strong purple fluorescent in dilute CH2Cl2solution, then show strong bluefluorescence in solid films; Their HOMO levels (-5.88~-5.99eV) are matched with ITO(-4.5~-5.0eV), LUMO levels (-2.64~-2.79eV) are closed to electronic transmissionmaterial PBD (-2.82eV); The results of TG curves show that their thermal decompositiontemperatures (Td) are394,324,304and487℃and they all have good thermal stability.Four compounds are expected to be as bipolar blue materials applied to OLEDs.2．Bipolar blue and green materials containing phenothiazine structureWith phenothiazine and phenanthrenequinone as raw materials, six novel phenanthr-oimidazole derivatives were synthesized:3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-ethyl-phenolthiazine(PBP1),3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-butyl-pheno-lthiazine (PBP2)3-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-hexyl-p-henothiazine(PBP3),3-(1-naphthyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-ethyl-phenol-thiazine(PNP1),3-(1-naphthyl-1H-phenanthnthro[9,10-d]imidazol-2-yl)-10-butyl-phenoth-iazine(PNP2) and3-(1-naphthyl-1H-phenanthro[9,10-d]imidazol-2-yl)-10-hexyl-phenothi-iazine(PNP3). Compounds PBP1~PBP3show strong blue fluorescence in dilute CH2Cl2solution and solid film, compound PNP1~PNP3have shown strong yellow-green or greenfluorescence in dilute CH2Cl2solution and solid film; Their HOMO levels (-5.61~-5.68eV) are matched with ITO (-4.5~-5.0eV), LUMO levels (-2.67~-2.83eV) are closed toelectronic transmission material PBD(-2.82eV); The results of TG curves show that theirthermal decomposition temperatures (Td) are respectively422,298,386,417,350and386 ℃, they all have good thermal stability. Six compounds are expected to be as bipolarblue and green materials applied to OLEDs.3．Bipolar green materials containing thiophenn structureWith phenothiazine,5-Formyl-2-thiophene boronic acid and phenanthrenequinoneas raw materials, six novel phenanthroimidazole derivatives wer synthesized:3-(5-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)thiophen-2-yl)-10-ethyl-phenothiazie(PBTP1),3-(5-(1-phenyl-1-H-phenanthro[9,10-d]imidazol-2-yl)thiophen-2-yl)-10-butyl-phenothiazine(PBTP2),3-(5-(1-phenyl-1Hphenanthro[9,10-d]imidazol-2-yl)thiophen-2-yl)-10-hexyl-phenothiazine(PBTP1),3-(5-(1-naphthyl-1H-phenanthro[9,10-d]imidazol-2-yl)thiophen-2-yl)-10-ethyl-phenothiazine(PNTP1),3-(5-(1-naphthyl-1H-phenanthro[9,10-d]imidazol-2-yl)thiophen-2-yl)-10-butyl-phenothiazine(PNTP2) and3-(5-(1-naphthyl-1H-phen-anthro[9,10-d] imidazol-2-yl)thiophen-2-yl)-10-hexyl-phenothiazine (PNTP3). The comp-ounds PBTP1~PBTP3and PNP1~PNP3all show strong green fluorescence in diluteCH2Cl2solution and solid film; Their HOMO levels (-5.57~-5.69eV) are matched withITO (-4.5~-5.0eV), LUMO levels (-2.83~-2.96eV) are closed to electronic transmissionmaterial Alq3(-3.1eV); The results of TG curves show that their thermal decompositiontemperatures (Td) are375,350,373,382,343and389℃respectively, they all have goodthermal stability. Six compounds are expected to be as bipolar green materials applied toOLEDs.