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

过渡金属配合物催化含氮多芳基化合物的新合成及其在有机EL器件中的应用

基本信息

批准号：
13555250
负责人：
INOUE Yoshio
金额：
$ 8.58万
依托单位：
Tohoku University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
2001
资助国家：
日本
起止时间：
2001 至 2004
项目状态：
已结题

项目摘要

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.

1.在钌络合物催化剂和碱的存在下，2-苯基吡啶与卤代芳烃反应，发现2-苯基吡啶苯环邻位发生直接芳基化反应。经过深入的研究，确定了该反应的最佳反应条件：钌配合物催化剂配位叔膦，其中[η^6-C_6H_6RuCl_2]_2-4PPh_3催化剂的活性最好。结果表明，以碳酸钾为碱，N-甲基吡咯烷为溶剂，反应温度为120℃，反应时间为20-40 h是反应的最佳条件。2.吡啶基是反应中不可避免的导向基团，通过与钌中心配位，促进了邻位导向反应。然而吡啶基很难转化为另一个官能团。开发易于转化的导向基团似乎是必要的。我们利用亚氨基和恶唑基作为芳环直接邻位芳基化的导向基团。这些基团可以很容易地转化为其他官能团：亚胺基可以转化为酮、醛、醇、胺，恶唑基可以转化为羧酸、酯和酰胺。3.利用上述反应方法制备了几种含氮多芳基化合物，并研究了它们作为有机电致发光器件的应用。它们是一种良好的电子传输材料，也是铱、铂配合物的良好配体，具有高效的磷光发光。