Modification Of 6-Fluoro-8-hydroxyquinoline At The 4-position By Electro-donating/Withdrawing Groups & The Iridium And Aluminum Phosphorescent/Fluorescent Complexes

Organic light-emitting diodes(OLEDs)have been extensively studied due to their potential applications for low driving voltage,easy fabrication,cost-effective,which has great potential in the filed of in color displays and white lightingIn this paper,a series of electron-with drawing/electron-donating group modified 4-substituted-6-fluor-8-hydroxyquinoline derivatives were synthesized.The CH3,Cl,H CF3,arylamine were introduced to the 4-position of 6-fluoro-8-hydroxyquinoline and the ligands were used as auxiliary ligands to obtain red-emitting phosphorescent iridium(Ⅲ)complexes and florescent materials aluminum(Ⅲ)complexes.The structures of target products and the intermediates were characterized by 1HNMR,and elementary analysis.Details are as follows:1.The series of 4-substituted-6-fluoro-8-Hydroxyquinoline ligands were synthesized starting from 5-fluoro-2-nitrophenol and 2-Amino-5-fluoro-phenol by the reaction of skraup,protecting reaction of hydroxide group,reduction reaction,ring closed reaction,the hydrolysis,dropping of carboxyl reaction and dropping of the protecting group reaction and so on.The series of the iridium(Ⅲ)complexes based on 2-phenylpyridine and the 4-substituted-6-fluoro-8-hydroxyquinoline ligands.The UV-vis absorption,fluorescence at 77 K,electrochemical in dichloromethane solution and solid fluorescence were investigated.The quantum efficiency was also obtained by using integral sphere.The quantum efficiency of the compound(the substituent respecetively for-CH3,H,Cl)is respectively for 6.0%,5.04%,4.92%.2.The series of Aluminum(Ⅲ)complexes based on the 4-substituted-6-fluoro-8-hydroxyquinoline ligands.The structure of product was characterized by elementary analysis and 1HNMR spectra.3.A novel phosphorescent ligand,4’-(2-pyridyl)-4",4’"-di[4-(9H-carbazol)-1,3,5-triphenylbenzene,was synthesized by diazotization Ullmann reaction,boronicacidification reaction and Suzuki coupling reaction from carbazole,1,4-dibrombenzene,4-bromobenzenamine and 1,3,5-tribromobenzene.The structure of target compound was confined by 1HNMR and elementary analysis.The UV-Vis and fluorescence spectra of target compound in dichloromethane solution were studied.