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NCN‐Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics
Author(s) -
Zych Dawid,
Kurpanik Aneta,
Slodek Aneta,
Maroń Anna,
Pająk Michał,
SzafraniecGorol Grażyna,
Matussek Marek,
Krompiec Stanisław,
SchabBalcerzak Ewa,
Kotowicz Sonia,
Siwy Mariola,
Smolarek Karolina,
Maćkowski Sebastian,
Danikiewicz Witold
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703324
Subject(s) - electroluminescence , thermal stability , oled , pyrene , biphenyl , photochemistry , oxadiazole , pyridine , chemistry , cycloaddition , photoluminescence , chemical stability , naphthalene , materials science , catalysis , organic chemistry , optoelectronics , layer (electronics)
Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4‐(2,2‐dimethylpropyloxy)pyridine ( P1 ), 4‐decyloxypyridine ( P2 ), 4‐pentylpyridine ( P3 ), 1‐decyl‐1,2,3‐triazole ( P4 ), and 1‐benzyl‐1,2,3‐triazole ( P5 ), are obtained through a Suzuki–Miyaura cross‐coupling reaction or Cu I ‐catalyzed 1,3‐dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1 – P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid‐state photo‐ and electroluminescence characteristics of selected compounds as organic light‐emitting diodes are tested. In the guest–host configuration, two matrixes, that is, poly( N ‐vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2‐tert‐butylphenyl‐5‐biphenyl‐1,3,4‐oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD‐DFT) provide a deeper understanding of the experimental results.