Design, Synthesis Of New Functionalized Tetraphenylporphyrin Derivatives

With various kinds, rich color, high color purity and good adjustability, organic optoelectronic materials have a broad prospect of applications in organic light-emiting diodes (OLEDs), organic laser diode, organic solar cells, chemical sensors, and so on. Among them, organic light emitting diodes satisfy the people's eagerness to high quality flat-panel display owing to self-luminous, high-brightness, wide viewing angle, high eontrast, thinness, low power consumption and fast response time. As one of saturated red luminescence materials, porphyrins greatly atrracted people's attentions recently. On the basis of a large amount of literatures investigation, we have designed and synthesised several new-type porphyrin derivatives. And the properties were also studied preliminarily which provided an experimental and theoretical referrence to application research of red luminescence materials. The main research contents are elaborated as follows:(1) We briefly described the structure characteristics of porphyrin, detailedly reviewed the applications of porphyrin in organic light-emitting materials, and discussed current research state of porphyrin as red light electroluminescent materials according to the literatures. Based on these, new concepts and design ideas for the dissertation hatched.(2) Through Adler condensation, Vilsmeier, Williamson substitution reaction Witting reaction, porphyrin derivatives G1, G2, G3 containing multi-carbazoles were obtained based TPPps. All the complexes were characterized by 1H-NMR and matrix assisted laser dissorption ironization time of flight mass spectrometry (MALDI-TOF MS). The UV-Vis, fluorescence, TGA, CV properties were investigated. The major absorption peaks of these compouds were at around 420 nm. And the absorbtion intensity present 1:2:3 with the increase of branch number. Their emission peaks were at around 660 nm, which demonstrates they were saturated red materials. They also have good thermal stability. Therefore, They have a potential of preparing electroluminescent device. The HOMO and LUMO energy levels, which can provide reference for OLEDs, were obtained from electrochemical and UV-Vis spectrum.(3) Cyclometalation organic ligands were synthesized by the solvent-free or an aqueous phase Aldol condensation and Michael addition. Through Knoevenagel reaction a series of compounds Y1,Y2,Y3,Y4,Y5,Y6,Y7,Y8,Y9 were obtained. And their structures were characterized using NMR and ESI-MS. Their optical properties were also investigated systematically. The absorptions of the compounds lie in 350-750 nm and the peaks of them are ca.410 nm. Their emission peaks were around 650nm. The absorption peaks have no apparent laws with the changes of polarity of the solvents as well as the emission peaks. The HOMO and LUMO energy levels were obtained from electrochemical and UV-Vis spectrum. Their thermal stabilities were also studied and the results showed they had good thermal stability.These results provid an experimental referrence to preparing of electroluminescent device..(4) Through Knoevenagel reaction a series of compounds with aggregation induced fluorescence enhancement effect (AIEE) were synthesized based on p-Phenylenediacetonitrile. And their structures were characterized preliminarily by NMR. The synthesis exploration to this kind of compounds provides reference for similar work.