Synthesis and light-emitting properties of 2-(N-phenyl-α-naphthylamino) and 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene  

作　　者：ZHANG WenGuan HE ZhiQun HUI GuanBao MU LinPing WANG YongSheng ZHAO ShengMin JING XiPing 

机构地区：[1]Key Laboratory of Luminescence and Optical Information,Ministry of Education,Institute of Optoelectronic Technology,Beijing Jiaotong University,Beijing 100044,China [2]Laboratory of Printing and Packaging Material and Technology and Beijing Area Major Laboratory,Beijing Institute of Graphic Communication,Beijing 102600,China [3]College of Chemistry and Molecular Engineering,Peking University,Beijing 100871,China

出　　处：《Science China Chemistry》2009年第7期952-960,共9页中国科学（化学英文版）

基　　金：Supported by the National Natural Science Foundation of China (Grant Nos. 20674004, 60776039, 60825407 & 10434030);Beijing Commission of Education (Grant No. KM200710015009);Beijing Sustentation Fund for Elitist (Grant No. 20041D0500410);Laboratory of Printing and Packaging Material and Technology and Beijing Area Major Laboratory Project (Grant No. KF200811);BJTU Fund (Grant No. 2006XM043)

摘　　要：A fluorescent organic triarylamine with a symmetric structure, 2,7-bis(N-α-naphthyl-phenylamino)-9,9- diethylfluorene (NPAEF) was synthesized using two methods, modified Ullmann coupling and modified palladium-catalyzed amination. An activated copper and a combination of Pd(OAc)2/P(t-Bu)3 and Pd(dba)2/P(t-Bu)3 were selected as catalysts to improve yields of reactions. These synthetic procedures were also successfully applied to an asymmetric 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene (BNPEF). Photoluminescent emission peaks in solid film and in diluted solution of NPAEF were both observed at 461 nm, while the main emission peaks of BNPEF appeared at 422 nm in hexane, and at 480 nm in methanol. The double emission peaks of BNPEF in hexane reflected fine structure in the vibrational state. With an increasing polarity of solvent, the main PL emission peaks were red-shifted and vibrational fine structure disappeared. Additionally, energy levels of NPAEF were investigated and an electroluminescence (EL) device of ITO/PVK:NPAEF/Al was fabricated, which showed a turn-on voltage of 9 V and peaked at 462 nm. The EL spectrum was in good agreement with PL spectrum, which indicated that they were from the same emitting center in the device.A fluorescent organic triarylamine with a symmetric structure, 2,7-bis(N-α-naphthyl-phenylamino)-9,9-diethylfluorene (NPAEF) was synthesized using two methods, modified Ullmann coupling and modified palladium-catalyzed amination. An activated copper and a combination of Pd(OAc)2/P(t-Bu)3 and Pd(dba)2/P(t-Bu)3 were selected as catalysts to improve yields of reactions. These synthetic procedures were also successfully applied to an asymmetric 2-dimesitylboron-7-(N-phenyl-α-naphthylamino)-9,9-diethylfluorene (BNPEF). Photoluminescent emission peaks in solid film and in diluted solution of NPAEF were both observed at 461 nm, while the main emission peaks of BNPEF appeared at 422 nm in hexane, and at 480 nm in methanol. The double emission peaks of BNPEF in hexane reflected fine structure in the vibrational state. With an increasing polarity of solvent, the main PL emission peaks were red-shifted and vibrational fine structure disappeared. Additionally, energy levels of NPAEF were investigated and an electroluminescence (EL) device of ITO/PVK:NPAEF/Al was fabricated, which showed a turn-on voltage of 9 V and peaked at 462 nm. The EL spectrum was in good agreement with PL spectrum, which indicated that they were from the same emitting center in the device.

关 键 词：CATALYSIS FLUORENE dimesitylboron TRIARYLAMINE LIGHT-EMITTING 

分 类 号：O625.1[理学—有机化学]