Studies On Synthesis And Properties Of Naphthalimide-based Organic Semiconductor Materials

With the development of science and technology, organic semiconductor materials related to inorganic semiconductors have showed many advantages, such as character in variety, the feature easy to modification in molecular structures and low costs. And they can be made into large thin, flexible devices. So they have become the focus of many researches in the aspect of electronic devices. Although the n type (electronic transfer) are less developed than the p type (hole-transporting) organic semiconductor materials because of their poor stability, low mobility. Their unique electrochemical properties of n type organic semiconductors are indispensable, so they have been widely studied in recent years.Naphthylimides as one kind of important n-type organic semiconductors have received extensive attention of scientists in recent years. Herein, we designed and synthesized a series of n type organic semiconductors based on two different structures of naphthylimide. The detailed contents are depicted as follows:1. We used 1,8-naphthylimide and 2,3-naphthylimide as skeletons, introduced fluorine atom into the former structure and the cyano group into the latter, and changed the alkyl chain of nitrogen unit. Then we synthesized six kinds of different naphthylimide compounds. These compounds all were confirmed by H NMR, C NMR and EI-MS.2-5 b,2-5 c and 2-10 a were also confirmed by X-ray diffraction. Their optoelectronic properties were investigated by UV-vis, PL and CV. The frontier orbital energy level distributions were also analyzed by DFT calculation. At the same time, we investigated the influence of electron-withdrawing groups on their optoelectronic properties and the effects of different alkyls on the packing model of molecules.2. By introducing three naphthalene imide groups into the 1,3,5 sites of the benzene ring, we got two different alkyls substituted star-shape molecular target compounds confirmed by 1H NMR,13C NMR and MALDI-TOF. The frontier orbital energy level distributions were also analyzed by DFT calculation. We investigated the influence of multiple naphthylimide groups on their optoelectronic properties.