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Synthesis, Electrochemical and Photophysical Properties, and Electroluminescent Performance of the Octa‐ and Deca(aryl)[60]fullerene Derivatives
Author(s) -
Matsuo Yutaka,
Sato Yoshiharu,
Hashiguchi Masahiko,
Matsuo Keiko,
Nakamura Eiichi
Publication year - 2009
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.200900021
Subject(s) - electroluminescence , materials science , fullerene , conjugated system , pyridine , photochemistry , fluorescence , quenching (fluorescence) , quantum yield , excited state , reagent , photoluminescence , oled , electrochemistry , polymer , chemistry , organic chemistry , nanotechnology , electrode , optoelectronics , physics , layer (electronics) , quantum mechanics , nuclear physics , composite material
Three multifunctionalized organo[60]fullerene derivatives, C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 5 Me 2 (cyclophenacene, 1 ), C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 5 Me 2 (fused corannulene, 2 ), and C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 3 Me 2 (phenylene‐bridged fused corannulene, 3 ) are synthesized by the reaction of C 60 Ph 5 Me with 4‐ tert ‐butylphenylcopper reagent in the presence of pyridine, followed by treatment with MeI. Compounds 1 – 3 undergo reduction in the range from −1.8 to −2.5 V versus Fc/Fc + and exhibit photoluminescence behavior with fluorescent quantum yields of 18.5%, 2.5%, and 3.2% with fluorescent lifetimes of 67, 1.1, and 27 ns ( 1 – 3 , respectively). Organic electroluminescent diode devices using 1 – 3 are fabricated with π‐conjugated polymers and show external electroluminescent efficiencies of 0.04%, 0.07%, and 0.03% emitting yellow, green, and red light, respectively. The device containing all three compounds emits white light. This result indicates that the bulky addends in 1 – 3 can effectively isolate the π‐conjugated systems of the molecules in the solid state and retard the intermolecular excited‐state quenching process.