Bis[3,5-difluoro-2-(2-pyrid­yl)phen­yl](picolinato)iridium(III)

Mao-Liang Xu; Guang-Bo Che; Xiu-Ying Li; Qi Xiao

doi:10.1107/S160053680804083X

. 2008 Dec 10;65(Pt 1):m28. doi: 10.1107/S160053680804083X

Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III)

Mao-Liang Xu ^a, Guang-Bo Che ^b,^*, Xiu-Ying Li ^b, Qi Xiao ^a

PMCID: PMC2967875 PMID: 21581501

Abstract

The Ir centre in the title complex, [Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)], is six-coordinated in a slightly distorted octahedral IrC₂N₃O fashion.

Related literature

For background to organic light-emitting diodes (OLEDs), see: Cai et al. (2008 ▶); Chen et al. (2007 ▶); Park et al. (2006 ▶). For the synthesis, see: Lamansky et al. (2001 ▶);

Experimental

Crystal data

[Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)]
M _r = 694.64
Orthorhombic,
a = 16.469 (3) Å
b = 14.677 (3) Å
c = 19.612 (4) Å
V = 4740.3 (16) Å³
Z = 8
Mo Kα radiation
μ = 5.70 mm⁻¹
T = 292 (2) K
0.30 × 0.26 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.203, T _max = 0.284
43036 measured reflections
5410 independent reflections
4239 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.066
S = 1.06
5410 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 2.31 e Å⁻³
Δρ_min = −1.47 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804083X/bt2823sup1.cif

e-65-00m28-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804083X/bt2823Isup2.hkl

e-65-00m28-Isup2.hkl^{(259.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

C11—Ir	1.997 (5)
C22—Ir	1.993 (4)
N1—Ir	2.041 (4)
N2—Ir	2.045 (4)
N3—Ir	2.138 (4)
Ir—O1	2.152 (3)

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C22—Ir—C11	88.95 (18)
C11—Ir—N1	81.53 (19)
N1—Ir—N2	175.14 (16)
N1—Ir—N3	93.78 (16)
C11—Ir—O1	95.02 (16)
N2—Ir—O1	93.88 (14)

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Acknowledgments

The authors thank the Key Programs Foundation for Science and Technology Development of Shanxi Province and the Foundation of Jilin Normal University.

supplementary crystallographic information

Comment

In recent decades, the long-lived excited-state and highly efficient solid-state emissions of d⁶ and d⁸ metal complexes have made them of interest as potential components in organic light-emitting diodes (OLEDs) (Chen et al., 2007). Particularly, phosphorescent materials like Ir³⁺ complexes can significantly improve electroluminescent performance because both singlet and triplet excitons can be harvested for light emission, and usually are used as very promising phosphor dyes in OLEDs (Park et al., 2006). Recently, blue organic phosphor such as F₂Irpic (F = 4,6-difluorophenylpyridinato-N,C-2' and pic = picolinate) (I) as a successful cyclometalated Ir³⁺ complex which has been typically doped into host matrices such as tetra-aryl silanes and short conjugation length carbazole derivatives in OLEDs, showing a good quantum efficiency (Cai et al., 2008). In this contribution, we synthesized and investigated crystal structure of F₂Irpic.

As shown in Fig. 1, each Ir³⁺ cation is in a distorted octahedral coordination geometry, consisting of two chelating cyclometalated F ligands with cis-C—C and trans-N—N dispositions and one pic ligand. The Ir—O distance being 2.152 Å and Ir—C and Ir—N lengths are in the range of 1.993–1.997 Å and 2.041–2.138 Å, respectively.

Experimental

The title complex was obtained in two steps using a standard method (Lamansky et al., 2001) (71% yield based on Ir).