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有机化学 ›› 2008, Vol. 28 ›› Issue (08): 1393-1397. 上一篇    下一篇

研究论文

苯并[de]蒽-7-酮类叔芳胺的合成及其发光性能的研究

余明新*,a,b ; 康君辉a ; 郑建鸿b   

  1. (a浙江大学化学系 杭州 310027)
    (b台湾清华大学化学系 新竹 30043)
  • 收稿日期:2007-10-13 修回日期:2008-01-03 发布日期:2008-08-18
  • 通讯作者: 余明新

Synthesis of Diarylamino-benzo[de]anthracen-7-ones and Their Light Emitting Property

YU, Ming-Xin*,a,b ; KANG, Jun-Hui a ; CHENG, Chien-Hong b   

  1. (a Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (b Department of Chemistry, Tsinghua University, Hsinchu 30043)
  • Received:2007-10-13 Revised:2008-01-03 Published:2008-08-18
  • Contact: YU, Ming-Xin

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芳基伯胺与芳基溴在Pd(dba)2/P(t-Bu)3催化下于80 ℃甲苯溶液中反应生成芳基仲胺, 芳基仲胺再与3-溴苯并[de]蒽-7-酮在Pd(OAc)2/P(t-Bu)3催化下于120 ℃邻二甲苯溶液中反应生成苯并[de]蒽-7-酮类叔芳胺有机电致发光材料; 3-二苯基氨基苯并[de]蒽-7-酮与丙二腈反应生成2-(3-二苯基氨基)苯并[de]蒽-7-基亚基丙二腈. 产物的结构经1H NMR, 13C NMR, 13C (DEPT), HRMS光谱所证实. 用UV-Vis, PL, DSC测定了化合物的发光性能.

关键词: 苯并[de]蒽-7-酮, 发光性能, 2-(3-二苯基氨基)苯并[de]蒽-7-基亚基丙二腈, 钯催化, 叔芳胺

The primary arylamines reacted with aryl halides to give the secondary arylamines by the catalysis of Pd(dba)2/P(t-Bu)3 at 80 ℃ in toluene. The secondary arylamines reacted with 3-bromo-benzo[de]- anthrax-cen-7-one to afford the organic light-emitting device (OLED) material of diarylamino- benzo[de]anthracen-7-ones type by the catalysis of Pd(OAc)2/P(t-Bu)3 at 120 ℃ in o-xylene. Reaction of 3-diphenylamino-benzo[de]anthracen-7-one with malononitrile gives 2-(3-diphenylamino-benzo[de]- anthracen-7-ylidene)-malononitrile. The product structures were demonstrated by 1H NMR, 13C NMR, 13C (DEPT), HRMS spectra. Light emitting properties were examined by UV-vis, PL and DSC spectra.

Key words: benzo[de]anthracen-7-one, tertiary arylamine, palladium catalyst, light emitting property, 2-(3-diphenylamino-benzo[de]anthracen-7-ylidene)-malononitrile