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Preparation via a NHC dimer complex, photophysical properties, and device performance of heteroleptic bis(tridentate) iridium(III) emitters

AuthorsAdamovich, Vadim; Boudreault, Pierre-Luc T.; Esteruelas, Miguel A. ; Gómez-Bautista, Daniel ; López, Ana M. ; Oñate, Enrique ; Tsai, Jui-Yi
Issue Date2019
PublisherAmerican Chemical Society
CitationOrganometallics 38(14): 2738-2747 (2019)
AbstractThe preparation, photophysical properties, and applicability to the fabrication of organic light-emitting diodes (OLEDs) of new phosphorescent bis(tridentate) [5t + 4t′] iridium(III) molecules are described. Treatment of [Ir(μ-OMe)(η4-COD)]2 (1; COD = 1,5-cyclooctadiene) with 5-tert-butyl-1,3-bis(3-isopropylimidazolium)benzene diiodide ([iPrHImC6H3(5-tBu)HImiPr][I]2), in the presence of KI, leads to [IrI(μ-I){κ3-C,C,C-[iPrImC6H2(5-tBu)ImiPr]}]2 (2). This complex reacts with 2-(1H-imidazol-2-yl)-6-phenylpyridine (HNImpyC6H5) and 2-(1H-benzimidazol-2-yl)-6-phenylpyridine (HNBzimpyC6H5), in the presence of Na2CO3, to afford the bis(tridentate) derivatives Ir{κ3-C,C,C-[iPrImC6H2(5-tBu)ImiPr]}{κ3-N,N,C-[NImpyC6H4]} (4) and Ir{κ3-C,C,C-[iPrImC6H2(5-tBu)ImiPr]}{κ3-N,N,C-[NBzimpyC6H4]} (5). Complexes 4 and 5 are phosphorescent emitters (λem 482–590 nm), which display observed lifetimes in the range 1.2–11.7 μs. They show high quantum yields in both doped poly(methyl methacrylate) films and in 2-methyltetrahydrofuran at room temperature (ϕ = 0.73–0.49). Complex 5 has been demonstrated to be suitable for use as a reasonably efficient phosphorescent greenish yellow emitter for OLED devices with an electroluminescence λmax of 552 nm and a maximum external quantum efficiency (EQE) of 12%.
Publisher version (URL)https://doi.org/10.1021/acs.organomet.9b00265
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