Studies On Synthesis And Properties Of N-type Organic Semiconducting Materials Based On 2,3-naphthylimide Block

According to the type of charge carrier,organic semiconducting materials can be classified into electron transporting(n-type)and hole transporters(p-type)materials,both have been explored in device applications in various fields due to potentially lower costs,simpler packaging and compatibility with flexible substrates.For example,n-type organic semiconducting materials,not only as a good candidate for electroluminescent acceptor material,heterojunction transistor material,photovoltaic cells,sensing material but also have a widly promising applications in p-n junction diodes,rectifier,integration loop circuit and so on.Especially,organic complementary circuits,comprising both p-and n-channel organic thin film transistors,fully favors various organic digital circuits and also is the basics of application of organic electronic devices owing to its low power dissipation,high operating speed,and good noise margin.Therefor,organic semiconductors have become the focus in materials science recently.The work bases on 2,3-naphthylene carboximides due to its strong intermolecular?-? stacking,which favors the orbital overlap and is crucial for obtaining high electron mobility.So,we begin with a series of research from both the perspectives of investigating substituent effect and expanding the core of 2,3-naphthylene carboximides,the main study appears as follows:1.Further functionalizations of 2,3-naphthylene carboximides was introduced with the Br-groups and CN-groups at 6,7 sites.So,6,7-dibromo 2,3-naphthylene carboximides and 6,7-dicyano 2,3-naphthylene carboximides were synthesized and confirmed by 1H NMR,13C NMR and mass spectra.In addition,the electro-optical properties were investigated using UV-vis absorption,fluorescence spectrometry and cyclic voltammetry(CV).An contrast has been made with 2,3-naphthylene carboximides to investigate substituent effect of Br-groups and CN-groups,moreover,density functional theory(DFT)has been used to optimize their structures and orbital energy.2.For big ?-delocalized functional molecules,triptycene and porphyrazine bearing naphthylene carboximides were synthesized by introduced 2,3-naphthylene carboximides into the rigid skeletons including triptycene and porphyrazine,and the effect on ?conjugated system also had been investigated.