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Iridium(III) Emitters Based on 1,4-disubstituted-1H-1,2,3-triazoles as Cyclometalating Ligand: Synthesis, Characterization, and Electroluminescent Devices

Iridium(III) Emitters Based on 1,4-disubstituted-1H-1,2,3-triazoles as Cyclometalating Ligand: Synthesis, Characterization, and Electroluminescent Devices

Jesús M Fernández-Hernández, Juan I Beltrán, Vincent Lemaur, Maria-Dolores Gálvez-López, Chen-Han Chien, Federico Polo, Enrico Orselli, Roland Fröhlich, Jérôme Cornil, Luisa De Cola

Inorg Chem. 2013 Feb 18;52(4):1812-24.

PMID: 23383706

Abstract:

A series of blue and blue-green emitters based on neutral bis- and tris-cyclometalated Ir(III) complexes with 1-benzyl-4-(2,6-difluorophenyl)-1H-1,2,3-triazole (dfptrBn) as cyclometalating ligand is reported. The bis-cyclometalated complexes of the type [Ir(dfptrBn)(2)(L(^)X)] with different ancillary ligands, L(^)X = picolinate (pic) (2) or 2-(5-(perfluorophenyl)-2H-1,2,4-triazol-3-yl)pyridine (pytrF(5)) (3), are described and their photophysical properties compared with the analogous complexes containing the archetypal 2-(2,4-difluorophenyl)pyridinato (dfppy) as cyclometaled ligand (C(^)N). Complex 2 exhibits a marked solvatochromic behavior, from 475 nm in toluene to 534 nm in formamide, due to the strong MLCT character of its emissive excited state. Complex 3 displays a true-blue emission, narrower in the visible part than FIrpic. In addition, the homoleptic complex [Ir(dfprBn)(3)] (4) and the heteroleptic compounds with mixed arylpyridine/aryltriazole ligands, [Ir(dfptrBn)(2)(C(^)N)] (C(^)N = 2-phenylpyridinato (ppy) (5) or dfppy (6)), have been synthesized and fully characterized. The facial (fac) complex fac-4 is emissive at 77 K showing a deep-blue emission, but it is not luminescent in solution at room temperature similarly to their phenylpyrazole counterparts. However, the fac isomers, fac-5 and fac-6, are highly emissive in solution and thin films, reaching emission quantum yields of 76%, with emission colors in the blue to blue-green region. The photophysical properties for all complexes have been rationalized by means of quantum-chemical calculations. In addition, we constructed electroluminescent devices, organic light-emitting diodes (OLEDs) by sublimation of fac-6, and by solution processed polymer-based devices (PLEDs) using complexes fac-5 or fac-6 as dopants.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP23195622	2-(1H-1,2,4-Triazol-3-yl)pyridine		23195-62-2	Price
AP387859703	Tris[2-(4,6-difluorophenyl)pyridinato-C2,N]iridium(III)		387859-70-3	Price

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