Synthesis and Characterization of a Multicomponent Rhenium(<scp>I</scp>) Complex for Application as an OLED Dopant

Lundin, Natasha J.; Blackman, Allan G.; Gordon, Keith C.; Officer, David L.

doi:10.1002/anie.200504532

Cited by 144 publications

(76 citation statements)

References 24 publications

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“…The SQUEEZE function identifies a 40-electron hole, consistent with this. The {Re(CO) 3 . This is partly due to the size of the rhenium ion which forces it to sit out of the plane of the bpy or phen ligands.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…1 [Re(CO) 3 py(OX)]PF 6 . A 0.15 g amount of [Re(CO) 3 Cl(OX)] (0.2 mmol) and 0.051 g of AgPF 6 (0.2 mmol) were refluxed in 50 mL of acetonitrile under N 2 in the dark for 18 h. The resulting yellow solution was filtered through Celite to remove the AgCl precipitate. A 10 mL amount of saturated aqueous NH 4 PF 6 was added to the filtrate.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The solid, assumed to be [Re(CO) 3 (CH 3 CN)OX]PF 6 , was reacted to form the pyridine adduct without characterization. A 0.16 g amount of [Re-(CO) 3 (CH 3 CN)OX]PF 6 (0.18 mmol) and 0.445 g of pyridine (5.63 mmol) were refluxed in 50 mL of methanol for 4 h. The resulting solution was reduced in volume to 25 mL under reduced pressure and refrigerated overnight. The resulting yellow solid was filtered and recrystallized from methanol.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Consequently, the ground and excited-state electronic structures, dipoles, and associated vibrational modes of [Re(CO) 3 Cl(bpy)], [Cu(PPh 3 ) 2 (bpy)] + , and related compounds are relatively well studied and known. 1,9−12 By appropriate functionalization, these complexes can be used to effect charge separation by photolysis or act as emissive centers under application of a potential.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Correct understanding of the photophysical properties that these substituents may induce is crucial in designing useful functional materials. While the {Re(CO) 3 Cl} moiety has been shown to be electron withdrawing, 21 in [Cu(PPh 3 ) 2 (bpy)] + and related compounds, the level of communication between the copper(I) and the ligand is relatively low. For MLCT transitions, the radical anion of the ligand can in theory be observed with little interference from the metal.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Photophysics of Oxadiazole- and Diphenylaniline-Substituted Re(I) and Cu(I) Complexes

et al. 2013

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Transition-metal complexes of the types [Re(CO)3Cl(NN)], [Re(CO)3py(NN)]+, and [Cu(PPh3)2(NN)]+, where NN = 4,4′-bis(5-phenyl-1,3,4-oxadiazol-2-yl)-2,2′-bipyridine (OX) and 4, 4′-bis(N,N-diphenyl-4-[ethen-1-yl]-aniline)-2,2′-bipyridine (DPA), have been synthesized and characterized. Crystal structures for [Re(CO)3Cl(DPA)] and [Cu(PPh3)2(OX)]BF4 are presented. The crystal structure of the rhenium complex shows a trans arrangement of the ethylene groups, in agreement with density functional theory calculations. The structure of the copper complex displays the planar aromatic nature of the bpy-oxadiazole ligand. Density functional theory modeling of the complexes was supported by comparison of calculated and experimental normalized Raman spectra; the mean absolute deviations of the complexes were <10 >cm-1. The Franck-Condon state was investigated using UV-vis and resonance Raman spectroscopic as well as density functional theory computational techniques. It was shown that the lowest energy absorption peaks are metal to ligand charge transfer and ligand-centered charge transfer for the oxadiazole-and diphenylaniline-substituted bipyridine ligands, respectively. The lowest energy excited states were characterized using transient emission and absorption spectroscopic techniques in conjunction with density functional theory calculations. These showed that the DPA complexes had ligand-centered nonemissive "dark" states with lifetimes ranging from 300 to 2000 ns. The crystal structure of the rhenium complex shows a trans arrangement of the ethylene groups, in agreement with density functional theory calculations. The structure of the copper complex displays the planar aromatic nature of the bpy−oxadiazole ligand. Density functional theory modeling of the complexes was supported by comparison of calculated and experimental normalized Raman spectra; the mean absolute deviations of the complexes were <10 cm −1 . The Franck−Condon state was investigated using UV−vis and resonance Raman spectroscopic as well as density functional theory computational techniques. It was shown that the lowest energy absorption peaks are metal to ligand charge transfer and ligand-centered charge transfer for the oxadiazole-and diphenylaniline-substituted bipyridine ligands, respectively. The lowest energy excited states were characterized using transient emission and absorption spectroscopic techniques in conjunction with density functional theory calculations. These showed that the DPA complexes had ligand-centered nonemissive "dark" states with lifetimes ranging from 300 to 2000 ns.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Photophysics of Oxadiazole- and Diphenylaniline-Substituted Re(I) and Cu(I) Complexes

et al. 2013

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Solution‐Processible Multi‐component Cyclometalated Iridium Phosphors for High‐Efficiency Orange‐Emitting OLEDs and Their Potential Use as White Light Sources

Wong

Zhou

et al. 2007

Adv Funct Materials

162

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The synthesis and photophysical studies of several multifunctional phosphorescent iridium(III) cyclometalated complexes consisting of the hole‐transporting carbazole and fluorene‐based 2‐phenylpyridine moieties are reported. All of them are isolated as thermally and morphological stable amorphous solids. Extension of the π‐conjugation through incorporation of electron‐pushing carbazole units to the fluorene fragment leads to bathochromic shifts in the emission profile, increases the highest occupied molecular orbital levels and improves the charge balance in the resulting complexes because of the propensity of the carbazole unit to facilitate hole transport. These iridium‐based triplet emitters give a strong orange phosphorescence light at room temperature with relatively short lifetimes in the solution phase. The photo‐ and electroluminescence properties of these phosphorescent carbazolylfluorene‐functionalized metalated complexes have been studied in terms of the coordinating position of carbazole to the fluorene unit. Organic light‐emitting diodes (OLEDs) using these complexes as the solution‐processed emissive layers have been fabricated which show very high efficiencies even without the need for the typical hole‐transporting layer. These orange‐emitting devices can produce a maximum current efficiency of ∼ 30 cd A–1 corresponding to an external quantum efficiency of ∼ 10 % ph/el (photons per electron) and a power efficiency of ∼ 14 lm W–1. The homoleptic iridium phosphors generally outperform the heteroleptic counterparts in device performance. The potential of exploiting these orange phosphor dyes in the realization of white OLEDs is also discussed.

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Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

Hayakawa

Ando

et al. 2008

Adv Funct Materials

257

130

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A new series of star‐shaped bipolar host molecules, tris(4′‐(1‐phenyl‐1H‐benzimidazol‐2‐yl)biphen‐yl‐4‐yl) amine (TIBN), tris(2′‐methyl‐4′‐(1‐phenyl‐1H‐benzimida zol‐2‐yl)biphenyl‐4‐yl)amine (Me‐TIBN), and tris(2,2′‐dimethyl‐4′‐(1‐phenyl‐1H‐benzimidazol‐2‐yl)biphenyl‐4‐yl)amine (DM‐TIBN), that contain hole‐transporting triphenylamine and electron‐transporting benzimidazole moieties are designed based on calculations using density functional theory and successfully prepared. The theoretical calculation of energy levels of TIBN derivatives affords helpful ideas to design molecules with a favorable localization of highest occupied/lowest unoccupied molecular orbital (HOMO/LUMO) levels and a predefined enhancement of the triplet energy gap. The TIBN derivatives are employed as hosts to fabricate phosphorescent organic light‐emitting diodes (OLEDs) by the two methods of spin‐coating and vacuum deposition. Notably, the spin‐coated Me‐TIBN and DM‐TIBN devices exhibit a much better performance than the vacuum‐deposited ones, in which the spin‐coated DM‐TIBN device (47 500 cd m−2, 27.3 cd A−1, 7.3 lm W−1) is outstanding with respect to other seminal work for solution‐processed OLEDs. More importantly, the new concept of localizing HOMO and LUMO levels for bipolar molecules is illustrated, and a facile strategy to tailor the energy levels by breaking the conjugation of hole‐ and electron‐transporting moieties is demonstrated.

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Synthesis and Characterization of a Multicomponent Rhenium(I) Complex for Application as an OLED Dopant

Cited by 144 publications

References 24 publications

Synthesis, Characterization, and Photophysics of Oxadiazole- and Diphenylaniline-Substituted Re(I) and Cu(I) Complexes

Synthesis, Characterization, and Photophysics of Oxadiazole- and Diphenylaniline-Substituted Re(I) and Cu(I) Complexes

Solution‐Processible Multi‐component Cyclometalated Iridium Phosphors for High‐Efficiency Orange‐Emitting OLEDs and Their Potential Use as White Light Sources

Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

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