Design,Synthesis And Optoelectronic Characterization Of Novel Anthracene Derivatives

Since the first organic field-effect transistor（OFET）was reported in 1987,researches on organic semiconductor materials have attracted extensive attention.Thousands of organic semiconductors have been reported.Compared with inorganic semiconductors,organic semiconductors take advantages of solution processability,intrinsic flexibility,and the ability for large-area printing.Meanwhile,they can be chemically modified to adjust the performance of devices and meet the needs of different functions.Among various organic semiconductors,polyacenes have been found to have good charge transport characteristics due to their large conjugated systems and demonstrate good field-effect performance.In this thesis,several novel anthracene derivatives have been designed and synthesized,and their optoelectronic property are investigated by OFET.The main contents are as follows:1.4-HDPA was designed and synthesized by introducing an asymmetric ethyl chain to 2,6-diphenylanthracene（DPA）in order to improve its molecular packing and solubility.Field-effect transistors based on its thin film and single crystal were prepared by thermal evaporation and physical vapor transport methods.The highest mobility of the two types of devices was 3.59 cm²V^-1s^-1 and 5.12 cm²V^-1s^-1,respectively.Compared with symmetrical molecular structures,the properties of the novel anthracene derivatives were improved obviously.2.Two new semiconductor materials of 1,5-di（anthracen-2-yl）naphthalene（1,5-DAN）and 2,5-di（anthracen-2-yl）thieno[3,2-b]thiophene（2,5-DATT）were synthesized by introducing anthracene units with high solid-state fluorescence quantum yield on naphthalene and dithiophene cores.Hole mobility of single crystals of 1,5-DAN and 2,5-DATT can be up to 8 cm²V^-1s^-1 and 1.2 cm²V^-1s^-1,respectively.At the same time,the solid fluorescence quantum yields of these two compounds are20.54%and 46.08%respectively.It is shown that 1,5-DAN possess high conjugation and dense molecular packing resulting in higher charge transfer performance.However,densely molecular packing quenches its solid state fluorescence to some extent.An ultraviolet phototransistor was prepared based on 2,5-DATT,which exhibited high responsivity of 1.5×10⁴ AW^-1,high sensitivity of 9×10⁶ and detectivity of 3×10¹⁵ Jones.