New synthesis of nitrogen-containing polyaryl compounds catalyzed by transitionmetal complexes and application to organic EL devices

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1.We observed that direct arylation of the ortho position in the benzene ring of 2-phenylpyridine took place when 2-phenylpyridine and aryl halides were reacted in the presence of a ruthenium complex catalyst and base. After intensive works, the best conditions were established for this important reaction as follows : Ruthenium complex catalysts coordinating tertiary phosphine, above all, [η^6-C_6H_6RuCl_2]_2-4PPh_3 showed the best performance in activity. The employment of potassium carbonate as base, N-methyl pyrrolidine as solvent, 120℃ as reaction temperature, 20-40 h as reaction time were found to be the best reaction conditions.2.Pyridyl group is inevitable for the reaction to occur as the directing group which facilitates the ortho directing reaction by coordinating the ruthenium center. However pyridyl group is hard to be converted into another functional group. Development of easily convertible directing group seems essential. We exploited imino and oxazoyl group as the directing group for the direct ortho arylation of the aromatic ring. These groups can easily be converted into other functional groups : Imino group can be converted into ketone, aldehyde, alcohol, amine, and oxazole group can be converted into carboxylic acid, ester, and amide.3.Then we prepared several nitrogen-containing polyaryl compounds utilizing above reaction method, and investigated the utility of these compounds as organic EL device. They were found to be good electron transporting material and also good ligand for iridium and platinum complexes with efficient phosphorescence luminescence.