Development of thiophene-fused phthalocyanines with high crystallinity and application to organic thin-film devices

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In order to improve device performance of organic field-effect transistors (OFETs) and organic photovoltaics (OPVs) based on phthalocyanines (Pcs), I have investigated properties of new porphyrazines with aromatic5-membered fused-ring heterocycle and its π-extended compound, and applied to organic thin-film devices. In this project, I have designed thiophene-fused porphyrazine (Tc), benzothiophene-fused porphyrazine (BTc), and thiadiazole-fused porphrazine (TzPz) as new Pcs. Alkylated Tc- and BTc-based devices showed p-channel characteristics with mobility of ～0.3 cm2 V^<-1>s^<-1> for Tc and ～10^<-2>cm^V^<-1>s^<-1>for BTc. However, alkylated TzPz-based devices showed no field-effect response. Alkylated Tc/C60bilayer OPV showed the efficiency of 1.2%. Whereas other Pcs-based OPVs showed no photovoltaics response. These results indicate that simple modification of molecule by π-extension leads to no improvement of device performance.