Efficient Green Light-Emitting Electrochemical Cells Based on Ionic Iridium Complexes with Sulfone-Containing Cyclometalating Ligands

A new approach to obtain green-emitting iridiumA complexes is described. The synthetic approach consists of introducing a methylsulfone electron-withdrawing substituent into a 4-phenylpyrazole cyclometalating ligand in order to stabilize the highest- occupied molecular orbital (HOMO). Six new complexes have been synthe- sized incorporating the conjugate base of 1-(4-(methylsulfonyl)phenyl)-1 H- pyrazole as the cyclometalating ligand. The complexes show green emission and very high photoluminescence quantum yields in both diluted and concentrated films. When used as the main active component in light-emit- ting electrochemical cells (LECs), green electroluminance is observed. High efficienci…

Host–guest blue light-emitting electrochemical cells

Carbazole, a commonly used hole-transporter for organic electronics, has been modified with an imidazolium cation and a hexafluorophosphate counter-anion to give an ionic hole-transporter. It has been applied as one of the hosts in a host–guest blue light-emitting electrochemical cell (LEC) with the neutral blue emitter FIrPic. We have obtained efficient and bright blue LECs with an electroluminescence maximum at 474 nm and efficacy of 5 cd A−1 at a luminance of 420 cd m−2, thereby demonstrating the potential of the ionic organic charge-transporters and of the host–guest architecture for LECs.

Thienylpyridine-based cyclometallated iridium(III) complexes and their use in solid state light-emitting electrochemical cells

The synthesis and characterization of four iridium(iii) complexes [Ir(thpy)2(N^N)][PF6] where Hthpy = 2-(2'-thienyl)pyridine and N^N are 6-phenyl-2,2'-bipyridine (1), 4,4'-di-(t)butyl-2,2'-bipyridine (2), 4,4'-di-(t)butyl-6-phenyl-2,2'-bipyridine (3) or 4,4'-dimethylthio-2,2'-bipyridine (4) are described. The single crystal structures of ligand 4 and the complexes containing the [Ir(thpy)2(1)](+) and [Ir(thpy)2(4)](+) cations have been determined. In [Ir(thpy)2(1)](+), the pendant phenyl ring engages in an intra-cation π-stacking interaction with one of the thienyl rings in the solid state, and undergoes hindered rotation on the NMR timescale in [Ir(thpy)2(1)](+) and [Ir(thpy)2(3)](+). The …

Solution, structural and photophysical aspects of substituent effects in the N^N ligand in [Ir(C^N)2(N^N)]+ complexes

The syntheses and properties of a series of eleven new [Ir(ppy)2(N^N)][PF6] complexes (Hppy = 2-phenylpyridine) are reported. The N^N ligands are based on 2,2-bipyridine (bpy), substituted in the 6- or 5-positions with groups that are structurally and electronically diverse. All but two of the N^N ligands incorporate an aromatic ring, designed to facilitate intra-cation face-to-face π-interactions between the N^N and one [ppy](-) ligand. Within the set of ligands, 6-(3-tolyl)-2,2'-bipyridine (5), 4,6-bis(4-nitrophenyl)-2,2'-bipyridine (9), and 4,6-bis(3,4,5-trimethoxyphenyl)-2,2'-bipyridine (10) are new and their characterization includes single crystal structures of 9, and two polymorphs o…

Bright and stable light-emitting electrochemical cells based on an intramolecularly π-stacked, 2-naphthyl-substituted iridium complex

The synthesis and characterization of a new cationic bis-cyclometallated iridium(III) complex and its use in solid-state light-emitting electrochemical cells (LECs) are described. The complex [Ir(ppy)2(Naphbpy)][PF6], where Hppy = 2-phenylpyridine and Naphbpy = 6-(2-naphthyl)-2,2′-bipyridine, incorporates a pendant 2-naphthyl unit that π-stacks face-to-face with the adjacent ppy− ligand and acts as a peripheral bulky group. The complex presents a structureless emission centred around 595–600 nm both in solution and in thin film with relatively low photoluminescence quantum yields compared with analogous systems. Density functional theory calculations support the charge transfer character of…

Highly Stable Red-Light-Emitting Electrochemical Cells

The synthesis and characterization of a series of new cyclometalated iridium(III) complexes [Ir(ppy) 2 (N ∧ N)][PF 6 ] in which Hppy = 2-phenylpyridine and N ∧ N is (pyridin-2-yl)benzo[ d ]thiazole ( L1 ), 2-(4-( tert -butyl)pyridin-2-yl)benzo[ d ]thiazole ( L2 ), 2-(6-phenylpyridin-2-yl)benzo[ d ]thiazole ( L3 ), 2-(4-( tert -butyl)-6-phenylpyridin-2-yl)benzo[ d ]thiazole ( L4 ), 2,6-bis(benzo[ d ]thiazol-2-yl)pyridine ( L5 ), 2-(pyridin-2-yl)benzo[ d ]oxazole ( L6 ), or 2,2′-dibenzo[ d ]thiazole ( L7 ) are reported. The single crystal structures of [Ir(ppy) 2 ( L1 )][PF 6 ]·1.5CH 2 Cl 2 , [Ir(ppy) 2 ( L6 )][PF 6 ]·CH 2 Cl 2 , and [Ir(ppy) 2 ( L7 )][PF 6 ] have been determined. The new com…

Flexible light-emitting electrochemical cells with single-walled carbon nanotube anodes

Abstract In this work, we demonstrate flexible solution processed light emitting electrochemical cells (LECs) which use single-walled carbon nanotubes (SWCNTs) films as the substrate. The SWCNTs were synthesized by an integrated aerosol method and dry-transferred on the plastic substrates at room temperature. The addition of a screen printed poly (3,4-ethylene dioxythiophene) doped with poly (styrene sulfonate) (PEDOT:PSS) film onto the nanostructured electrode further homogenizes the surface and enlarges the work function, enhancing the hole injection into the active layer. By using an efficient phosphorescent ionic transition metal complex (iTMC) as the active material, efficacies up to 9…

Luminescent osmium(II) bi-1,2,3-triazol-4-yl complexes: photophysical characterisation and application in light-emitting electrochemical cells

The series of osmium(II) complexes [Os(bpy)3-n(btz)n][PF6]2 (bpy = 2,2’-bipyridyl, btz = 1,1’-dibenzyl-4,4’-bi-1,2,3-triazolyl, 1 n = 0, 2 n = 1, 3 n = 2, 4 n = 3), have been prepared and characterised. The progressive replacement of bpy by btz leads to blue-shifted UV-visible electronic absorption spectra, indicative of btz perturbation of the successively destabilised bpy-centred LUMO. For 4, a dramatic blue-shift relative to the absorption profile for 3 is observed, indicative of the much higher energy LUMO of the btz ligand over that of bpy, mirroring previously reported data on analogous ruthenium(II) complexes. Unlike the previously reported ruthenium systems, heteroleptic complexes 2…

[Ir(C^N)2(N^N)]+ emitters containing a naphthalene unit within a linker between the two cyclometallating ligands

The synthesis of four cyclometallated [Ir(C^N) 2 (N^N)][PF 6 ] compounds in which N^N is a substituted 2,2’- -bipyridine (bpy) ligand and the naphthyl-centred ligand 2,7-bis(2-(2-(4-(pyridin-2-yl)phenoxy)ethoxy) ethoxy)naphthalene provides the two cyclometallating C^N units is reported. The iridium( III ) complexes have been characterized by 1 H and 13 C NMR spectroscopies, mass spectrometry and elemental analysis, and their electrochemical and photophysical properties are described. Comparisons are made with a model [Ir(ppy) 2 (N^N)][PF 6 ] compound (Hppy = 2-phenylpyridine). The complexes containing the naphthyl-unit exhibit similar absorption spectra and excitation at 280 nm leads to an …

Operating Modes of Sandwiched Light-Emitting Electrochemical Cells

Light-emitting electrochemical cells (LECs) are promising lighting devices in which the redistribution of ionic charges allows for double electronic carrier injection from air-stable electrodes. Uncertainties about the mode of operation are limiting the progress of these devices. Using fast (with respect to the current growth time) but resolutive electrical measurement techniques, the electronic transport mechanism in state-of-the-art sandwiched devices can be monitored as a function of the operation time. The results indicate the formation of doped transport layers adjacent to the electrodes that reduces the extent of the central neutral light-emitting layer where electronic transport is l…

Modulation of the solubility of luminescent semiconductor nanocrystals through facile surface functionalization

The solubility of luminescent quantum dots in solvents from hexane to water can be finely tuned by the choice of the countercations associated with carboxylate residues present on the nanocrystal surface. The resulting nanocrystals exhibit long term colloidal and chemical stability and maintain their photophysical properties.

Regioisomerism in cationic sulfonyl-substituted [Ir(C^N)2(N^N)]+ complexes: its influence on photophysical properties and LEC performance

A series of regioisomeric cationic iridium complexes of the type [Ir(C^N)2(bpy)][PF6] (bpy = 2,2'-bipyridine) is reported. The complexes contain 2-phenylpyridine-based cyclometallating ligands with a methylsulfonyl group in either the 3-, 4- or 5-position of the phenyl ring. All the complexes have been fully characterized, including their crystal structures. In acetonitrile solution, all the compounds are green emitters with emission maxima between 493 and 517 nm. Whereas substitution meta to the Ir-C bond leads to vibrationally structured emission profiles and photoluminescence quantum yields of 74 and 77%, placing a sulfone substituent in a para position results in a broad, featureless em…

Nontemplate Synthesis of CH3NH3PbBr3 Perovskite Nanoparticles

To date, there is no example in the literature of free, nanometer-sized, organolead halide CH3NH3PbBr3 perovskites. We report here the preparation of 6 nm-sized nanoparticles of this type by a simple and fast method based on the use of an ammonium bromide with a medium-sized chain that keeps the nanoparticles dispersed in a wide range of organic solvents. These nanoparticles can be maintained stable in the solid state as well as in concentrated solutions for more than three months, without requiring a mesoporous material. This makes it possible to prepare homogeneous thin films of these nanoparticles by spin-coating on a quartz substrate. Both the colloidal solution and the thin film emit l…

Iridium(III) Complexes with Phenyl-tetrazoles as Cyclometalating Ligands

Ir(II) cationic complexes with cyclometalating tetrazolate ligands were prepared for the first time, following a two-step strategy based on (i) a silver-assisted cyclometalation reaction of a tetrazole derivative with IrCl3 affording a bis-cyclometalated solvato-complex P ([Ir(ptrz)(2)(CH3CN)(2)](+), Hptrz = 2-methyl-5-phenyl-2H-tetrazole); (ii) a substitution reaction with five neutral ancillary ligands to get [Ir(ptrz)(2)L](+), with L = 2,2'-bypiridine (1), 4,4'-di-tert-butyl-2,2'-bipyridine (2), 1,10-phenanthroline (3), and 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine (4), and [Ir(ptrz)(2)L-2](+), with L = tertbutyl isocyanide (5). X-ray crystal structures of P, 2, and 3 were solved. Elect…

Colour tuning by the ring roundabout: [Ir(C^N)2(N^N)]+ emitters with sulfonyl-substituted cyclometallating ligands

A series of cationic bis-cyclometallated iridium(III) complexes [Ir(C^N)2(N^N)]+ is reported. Cyclometallating C^N ligands are based on 2-phenylpyridine with electron-withdrawing sulfone substituents in the phenyl ring: 2-(4-methylsulfonylphenyl)pyridine (H1) and 2-(3-methylsulfonylphenyl)pyridine (H2). 2-(1H-Pyrazol-1-yl)pyridine (pzpy) and 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine (dmpzpy) are used as electron-rich ancillary N^N ligands. The complexes have been fully characterized and the single crystal structure of [Ir(2)2(dmpzpy)][PF6]·MeCN has been determined. Depending on the position of the methylsulfonyl group, the complexes are green or blue emitters with vibrationally structured em…

Efficient orange light-emitting electrochemical cells

We report the first bis-cyclometalated cationic iridium(III) complex with N-aryl-substituted 1H-imidazo [4,5-f][1,10]phenanthroline. The complex emits yellow-orange phosphorescence with a maximum at 583 nm, a quantum yield of 43%, and an excited-state lifetime of 910 ns in argon-saturated dichloromethane. Optimized orange light-emitting electrochemical cells with the new Ir(III) complex exhibit fast turn-on, a peak luminance of 684 cd m(-2) and a peak efficacy of 6.5 cd A(-1); in 850 h of continuous operation their luminance and efficacy decrease only by 20%.

Dipole reorientation and local density of optical states influence the emission of light-emittingelectrochemical cells

Herein, we analyze the temporal evolution of the electroluminescence of light-emitting electrochemicalcells (LECs), a thin-film light-emitting device, in order to maximize the luminous power radiated bythese devices. A careful analysis of the spectral and angular distribution of the emission of LECsfabricated under the same experimental conditions allows describing the dynamics of the spatial regionfrom which LECs emit,i.e.the generation zone, as bias is applied. This effect is mediated by dipolereorientation within such an emissive region and its optical environment, since its spatial drift yields adifferent interplay between the intrinsic emission of the emitters and the local density of …

Shine bright or live long: substituent effects in [Cu(N^N)(P^P)]+-based light-emitting electrochemical cells where N^N is a 6-substituted 2,2'-bipyridine

We report [Cu(P^P)(N^N)][PF6] complexes with P^P = bis(2-(diphenylphosphino)phenyl)ether (POP) or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) and N^N = 6-methyl-2,2′-bipyridine (Mebpy), 6-ethyl-2,2′-bipyridine (Etbpy), 6,6′-dimethyl-2,2′-bipyridine (Me2bpy) or 6-phenyl-2,2′-bipyridine (Phbpy). The crystal structures of [Cu(POP)(Phbpy)][PF6]·Et2O, [Cu(POP)(Etbpy)][PF6]·Et2O, [Cu(xantphos)(Me2bpy)][PF6], [Cu(xantphos)(Mebpy)][PF6]·CH2Cl2·0.4Et2O, [Cu(xantphos)(Etbpy)][PF6]·CH2Cl2·1.5H2O and [Cu(xantphos)(Phbpy)][PF6] are described; each copper(I) centre is distorted tetrahedral. In the crystallographically determined structures, the N^N domain in [Cu(xantphos)(Phbpy)]+ and [Cu(…

p–n Metallophosphor based on cationic iridium(iii) complex for solid-state light-emitting electrochemical cells

An ionic transition-metal complex for improved charge transporting properties was designed, containing both n-type dimesitylboryl (BMes2) and p-type carbazole groups. The complex, [Ir(Bpq)2(CzbpyCz)]PF6 (1) (Bpq = 2-[4-(dimesitylboryl)phenyl] quinoline, CzbpyCz = 5,5′-bis(9-hexyl-9H-carbazol-3-yl)-2,2′-bipyridine) and its equivalent in which the BMes2 groups were substituted with carbazole moieties were evaluated on the photoluminescence and excited state properties in detail. According to the photophysical and electrochemical properties, we concluded that the BMes2 groups can increase the conjugation length of the cyclometalated C^N ligands and greatly enhance the phosphorescence efficienc…

Twisted hexaazatrianthrylene: synthesis, optoelectronic properties and near-infrared electroluminescent heterojunctions thereof

The synthesis, optoelectronic properties and near-infrared electroluminescent heterojunctions of a twisted and soluble 7,8,15,16,23,24-hexaazatrianthrylene derivative are reported.

Pyrene-fused bisphenazinothiadiazoles with red to NIR electroluminescence

The synthesis and characterisation of two pyrene-fused phenazinothiadiazole derivatives with different substituents is described. Light-emitting diodes incorporating such derivatives display red to near-infrared electroluminescence with emission peaks at wavelengths as long as 721 nm, illustrating that pyrene-fused bisphenazinothiadiazoles can serve as deep red and NIR emitters.

Improving the Turn-On Time of Light-Emitting Electrochemical Cells without Sacrificing their Stability

The luminance, efficiency, and turn-on time of ionic iridium complex-based light-emitting electrochemical cells can be improved by inserting an ionic liquid with high intrinsic conductivity. This results in a device in which the decrease in turn-on time is achieved while maintaining the stability.

Efficient photovoltaic and electroluminescent perovskite devices.

Planar diode structures employing hybrid organic–inorganic methylammonium lead iodide perovskites lead to multifunctional devices exhibiting both a high photovoltaic efficiency and good electroluminescence. The electroluminescence strongly improves at higher current density applied using a pulsed driving method.

Light-emitting electrochemical cells: recent progress and future prospects

We provide a short review on light-emitting electrochemical cells (LECs), one of the simplest kinds of electroluminescent devices. In their simplest form, they consist of just one active layer containing an emitter and a salt. They operate with low voltages, which allows for high power efficiencies, and air-stable electrodes, which simplifies the encapsulation requirements. The aim of this review is to highlight the recent advances and the main remaining challenges. We describe the current understanding of their peculiar operation mechanism and focus on the major concepts used to improve their performance.

Red emitting [Ir(C^N)2(N^N)]+ complexes employing bidentate 2,2':6,2''-terpyridine ligands for light-emitting electrochemical cells

2,2':6',2''-Terpyridine (tpy), 4'-(4-HOC6H4)-2,2':6',2''-terpyridine (1), 4'-(4-MeOC6H4)-2,2':6',2''-terpyridine (2), 4'-(4-MeSC6H4)-2,2':6',2''-terpyridine (3), 4'-(4-H2NC6H4)-2,2':6',2''-terpyridine (4) and 4'-(4-pyridyl)-2,2':6',2''-terpyridine (4) act as N^N chelates in complexes of the type [Ir(C^N)2(N^N)][PF6] in which the cyclometallating ligand, C^N, is derived from 2-phenylpyridine (Hppy) or 3,5-dimethyl-1-phenyl-1H-pyrazole (Hdmppz). The single crystal structures of eight complexes have been determined, and in each iridium(III) complex cation, the non-coordinated pyridine ring of the tpy unit is involved in a face-to-face π-stacking interaction with the cyclometallated ring of an …

Low Current Density Driving Leads to Efficient, Bright and Stable Green Electroluminescence

Electroluminescent devices have the potential to reshape lighting and display technologies by providing low-energy consuming solutions with great aesthetic features, such as flexibility and transparency. In particular, light-emitting electrochemical cells (LECs) are among the simplest electro-luminescent devices. The device operates with air-stable materials and the active layer can be resumed to an ionic phosphorescent emitter. As a consequence, LECs can be assembled using solution-process technologies, which could allow for low-cost and large-area lighting applications in the future. High efficiencies have been reported at rather low luminances (<50 cd m(-2)) and at very low current densi…

Exploring the effect of the cyclometallating ligand in 2-(pyridine-2-yl)benzo[d]thiazole-containing iridium(III) complexes for stable light-emitting electrochemical cells

The preparation and characterization of a series of iridium(III) ionic transition-metal complexes for application in light-emitting electrochemical cells (LECs) are reported. The complexes are of the type [Ir(C^N)2(N^N)][PF6] in which C^N is one of the cyclometallating ligands 2-(3-(tert-butyl)phenyl)pyridine (tppy), 2-phenylbenzo[d]thiazole (pbtz), 1-phenyl-1H-pyrazole (ppz) and 1-phenylisoquninoline (piq), and N^N is 2-(pyridine-2-yl)benzo[d]thiazole (btzpy). The variation in the C^N ligands allows the HOMO energy level to be tuned, leading to HOMO–LUMO gaps in the range 2.76–3.01 eV and values of Eox1/2 of 0.81–1.11 V. In solution, the complexes are orange to deep-red emitters (λmax in t…

Peripheral halo-functionalization in [Cu(N^N)(P^P)]+ emitters: influence on the performances of light-emitting electrochemical cells

A series of heteroleptic [Cu(N^N)(P^P)][PF6] complexes is described in which P^P = bis(2-(diphenylphosphino)phenyl)ether (POP) or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) and N^N = 4,4′-diphenyl-6,6′-dimethyl-2,2′-bipyridine substituted in the 4-position of the phenyl groups with atom X (N^N = 1 has X = F, 2 has X = Cl, 3 has X = Br, 4 has X = I; the benchmark N^N ligand with X = H is 5). These complexes have been characterized by multinuclear NMR spectroscopy, mass spectrometry, elemental analyses and cyclic voltammetry; representative single crystal structures are also reported. The solution absorption spectra are characterized by high energy bands (arising from ligand-c…

Increasing the efficiency of light-emitting electrochemical cells by limiting the exciton quenching

ABSTRACTLight-emitting electrochemical cells (LECs) are one of the simplest electroluminescent devices. The possibility to be processed from solution and to operate with air-stable materials makes them an attractive alternative to organic light emitting diodes (OLEDs). Still their efficiencies are below those obtained in OLEDs. Additionally the best efficiencies were reported at low luminances and sustained for a short period of time. Here we show that for a LEC employing an orange-emitting charged iridium complex that is driven using a pulsed driving scheme high efficiencies of up to 20.5 cd A-1 can be obtained at high luminance and sustained over the device lifetime. It is also shown that…

Molecular Engineering of Iridium Blue Emitters Using Aryl N‐Heterocyclic Carbene Ligands

The synthesis of a new series of neutral bis[2-(2,4-difluorophen-2-yl)pyridine][1-(2-aryl)-3-methylimidazol-2-ylidene]iridium(III) complexes is reported. Each complex has been characterized by NMR spectroscopy, UV/Vis spectrophotometry, and cyclic voltammetry, and the photophysical properties examined in depth. Furthermore, two of the complexes have been characterized by single-crystal X-ray diffraction analysis. By systematically modifying the cyclometalating aryl group on the N-heterocyclic carbene (NHC) ligand from 2,4-dimethoxyphenyl to 6-methoxy-2-methyl-3-pyridyl, the energy levels of the Ir complexes were modified to produce new blue emitters with increased HOMO and triplet-state ene…

Anionic Cyclometalated Iridium(III) Complexes with a Bis-Tetrazolate Ancillary Ligand for Light-Emitting Electrochemical Cells

none 10 si A series of monoanionic Ir(III) complexes (2-4) of general formula [Ir(C^N)2(b-trz)](TBA) are presented, where C^N indicates three different cyclometallating ligands (Hppy = 2-phenylpyridine; Hdfppy = 2-(2,4-difluoro-phenyl)pyridine; Hpqu = 2-methyl-3-phenylquinoxaline), b-trz is a bis-tetrazolate anionic N^N chelator (H2b-trz = di(1H-tetrazol-5-yl)methane), and TBA = tetrabutylammonium. 2-4 are prepared in good yields by means of the reaction of the suitable b-trz bidentate ligand with the desired iridium(III) precursor. The chelating nature of the ancillary ligand, thanks to an optimized structure and geometry, improves the stability of the complexes, which have been fully char…

Phosphane tuning in heteroleptic [Cu(N^N)(P^P)]+ complexes for light-emitting electrochemical cells

The synthesis and characterization of five [Cu(P^P)(N^N)][PF 6 ] complexes in which P^P = 2,7-bis( tert -butyl)-4,5-bis(diphenylphosphino)-9,9-dimethylxanthene ( t Bu 2 xantphos) or the chiral 4,5-bis(mesitylphenylphosphino)-9,9-dimethylxanthene (xantphosMes 2 ) and N^N = 2,2'-bipyridine (bpy), 6-methyl-2,2'-bipyridine (6-Mebpy) or 6,6'-dimethyl-2,2'-bipyridine (6,6'-Me 2 bpy) are reported. Single crystal structures of four of the compounds confirm that the copper(I) centre is in a distorted tetrahedral environment. In [Cu(xantphosMes 2 )(6-Mebpy)][PF 6 ], the 6-Mebpy unit is disordered over two equally populated orientations and this disorder parallels a combination of two dynamic processe…

Fine‐Tuning of Photophysical and Electronic Properties of Materials for Photonic Devices Through Remote Functionalization

We report four new iridium(III) complexes of the type [Ir(ppy)2(N?N)][PF6] in which N?N is a 4,6-diphenyl-2,2`-bipyridine and the 4-phenyl ring is substituted at either the para or meta positions [4-Me, N?N = 1; 4-Br, N?N = 2; 3,5-Br2, N?N = 3; 3,5-(C6H4-4-NPh2)2, N?N = 4]. The complexes have been fully characterized, and single-crystal diffraction analyses of [Ir(ppy)2(N?N)][PF6] (N?N = 13) confirmed that each [Ir(ppy)2(N?N)]+ cation exhibits face-to-face p-stacking between the pendant phenyl substituent of the N?N ligand and the cyclometallated phenyl ring of an adjacent [ppy] ligand. In solution, the complexes are short-lived emitters; the emission maxima for [Ir(ppy)2(1)][PF6], [Ir(ppy)…

Stable and Efficient Solid-State Light-Emitting Electrochemical Cells Based on a Series of Hydrophobic Iridium Complexes

Light-emitting electrochemical cells (LECs) based on ionic transition-metal complexes (iTMCs) exhibiting high efficiency, short turn-on time, and long stability have recently been presented. Furthermore, LECs emitting in the full range of the visible spectrum including white light have been reported. However, all these achievements were obtained individually, not simultaneously, using in each case a different iTMC. In this work, device stability is maintained by employing intrinsically stable ionic iridium complexes, while increasing the complex and the device quantum yields for exciton-to-photon conversion. This is done by sequentially modifying the archetype ionic iridium complex [Ir(ppy)…

Light-Emitting Electrochemical Cells Using Cyanine Dyes as the Active Components

Light-emitting electrochemical cells (LECs) based on cyanine molecules were prepared. High photoluminescence quantum yields were obtained for host-guest films using two cyanine dyes, reaching 27%. Sandwiching these films in between two electrodes allows for very stable near-infrared emission with a maximum radiant flux of 1.7 W m(-2) at an external quantum efficiency of 0.44%.

Correlating the Lifetime and Fluorine Content of Iridium(III) Emitters in Green Light-Emitting Electrochemical Cells

In light-emitting electrochemical cells, the lifetime of the device is intrinsically linked to the stability of the phosphorescent emitter. In this study, we present a series of ionic iridium(III) emitters based on cyclometalating phenylpyridine ligands whose fluorine substituents are varied in terms of position and number. Importantly, despite these structural modifications, the emitters exhibit virtually identical electrochemical and spectroscopic properties, which allows for proper comparison in functional devices. Quantum chemical calculations support the properties measured in solution and suggest great similarities regarding the electronic structures of the emitters. In electrolumines…

Pulsed-current versus constant-voltage light-emitting electrochemical cells with trifluoromethyl-substituted cationic iridium(iii) complexes

We report on five cationic iridium(III) complexes with cyclometalating 2-(3′-trifluoromethylphenyl)pyridine and a diimine, [(C⁁N)2Ir(N⁁N)](PF6), N⁁N = 4,4′-R2-2,2′-dipyridyl or 4,7-R2-1,10-phenanthroline (R = H, Me, tert-Bu, Ph), and characterize three of them by crystal structure analysis. The complexes undergo oxidation of the Ir–aryl fragment at 1.13–1.16 V (against ferrocene couple) and reduction of the N⁁N ligand at −1.66 V to −1.86 V, and have a redox gap of 2.84–2.99 V. The complexes exhibit bluish-green to green-yellow phosphorescence in an argon-saturated dichloromethane solution at room temperature with a maximum at 486–520 nm, quantum yield of 61–67%, and an excited-state lifetim…

Light-emitting electrochemical cells and solution-processed organic light-emitting diodes using small molecule organic thermally activated delayed fluorescence emitters

EZ-C thanks the University of St Andrews for support. The authors are grateful to the EPSRC for financial support (grants EP/J01771X and EP/J00916). IDWS is a Royal Society Wolfson Research Merit Award Holder. Two novel charged organic thermally activated delayed fluorescence (TADF) emitters, 1 and 2, have been synthesized. Their TADF behavior is well-supported by the multiexponential decay of their emission (nanosecond and microsecond components) and the oxygen dependence of the photoluminescence quantum yields. Spin-coated electroluminescent devices have been fabricated to make light-emitting electrochemical cells (LEECs) and organic light-emitting diodes (OLEDs). The first example of a n…

CF3 Substitution of [Cu(P^P)(bpy)][PF6 ] Complexes: Effects on Photophysical Properties and Light-Emitting Electrochemical Cell Performance

Herein, [Cu(P^P)(N^N)][PF6 ] complexes (P^P=bis[2-(diphenylphosphino)phenyl]ether (POP) or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos); N^N=CF3 -substituted 2,2'-bipyridines (6,6'-(CF3 )2 bpy, 6-CF3 bpy, 5,5'-(CF3 )2 bpy, 4,4'-(CF3 )2 bpy, 6,6'-Me2 -4,4'-(CF3 )2 bpy)) are reported. The effects of CF3 substitution on their structure as well as their electrochemical and photophysical properties are also presented. The HOMO-LUMO gap was tuned by the N^N ligand; the largest redshift in the metal-to-ligand charge transfer (MLCT) band was for [Cu(P^P){5,5'-(CF3 )2 bpy}][PF6 ]. In solution, the compounds are weak yellow to red emitters. The emission properties depend on the substitu…

Chloride ion impact on materials for light-emitting electrochemical cells

Small quantities of Cl(-) ions result in dramatic reductions in the performance of ionic transition metal complexes in light-emitting electrochemical cells. Strong ion-pairing between aromatic protons and chloride has been established in both the solid state and solution. X-ray structural determination of 2{[Ir(ppy)2(bpy)][Cl]}·2CH2Cl2·[H3O]·Cl reveals the unusual nature of an impurity encountered in the preparation of [Ir(ppy)2(bpy)][PF6].

Exceptionally long-lived light-emitting electrochemical cells: multiple intra-cation π-stacking interactions in [Ir(C^N)2(N^N)][PF6] emitters

A series of cyclometalated iridium(iii) complexes [Ir(C^N)2(N^N)][PF6] (N^N = 2,2′-bipyridine (1), 6-phenyl-2,2′-bipyridine (2), 4,4′-di-tert-butyl-2,2′-bipyridine (3), 4,4′-di-tert-butyl-6-phenyl-2,2′-bipyridine (4); HC^N = 2-(3-phenyl)phenylpyridine (HPhppy) or 2-(3,5-diphenyl)phenylpyridine (HPh2ppy)) are reported. They have been synthesized using solvento precursors so as to avoid the use of chlorido-dimer intermediates, chloride ion contaminant being detrimental to the performance of [Ir(C^N)2(N^N)][PF6] emitters in light-electrochemical cell (LEC) devices. Single crystal structure determinations and variable temperature solution 1H NMR spectroscopic data confirm that the pendant pheny…

[Cu(bpy)(P^P)]+ containing light-emitting electrochemical cells: improving performance through simple substitution

Light-emitting electrochemical cells (LECs) containing [Cu(POP)(N^N)][PF6] (POP = bis(2-diphenylphosphinophenyl)ether, N^N = 6-methyl- or 6,6′-dimethyl-2,2′-bipyridine) exhibit luminance and efficiency surpassing previous copper(i)-containing LECs.

Enhancing the photoluminescence quantum yields of blue-emitting cationic iridium(iii) complexes bearing bisphosphine ligands

EZ-C acknowledges the University of St Andrews for financial support. We thank Johnson Matthey and Umicore AG for the gift of materials and Cihang Yu for the preparation of isopropxantphos. We thank Dr. Nail Shaveleev for the synthesis of NMS25. IDWS and AKB acknowledge support from EPSRC (EP/J01771X). This work has been supported by the Spanish Ministry of Economy and Competitiveness (MINECO) MAT2014-55200. Herein we present a structure-property relationship study of thirteen cationic iridium (III) complexes of the form of [Ir(C^N)2(P^P)]PF6 in both solution and the solid state through systematic evaluation of six bisphosphine (P^P) ligands (xantphos, dpephos, dppe, Dppe, nixantphos and is…

Front Cover: CF3 Substitution of [Cu(P^P)(bpy)][PF6 ] Complexes: Effects on Photophysical Properties and Light-Emitting Electrochemical Cell Performance (ChemPlusChem 4/2018)

Deep-blue thermally activated delayed fluorescence (TADF) emitters for light-emitting electrochemical cells (LEECs)

The authors acknowledge the University of St Andrews for financial support. The authors also acknowledge financial support from the European Union H2020 project INFORM (grant 675867), the Spanish Ministry of Economy and Competitiveness (MINECO) via the Unidad de Excelencia María de Maeztu MDM-2015-0538, MAT2014-55200 and the Generalitat Valenciana (Prometeo/2016/135). MLP acknowledges support from a Grisolia grant (GRISOLIA/2015/A/146). Two deep blue thermally activated delayed fluorescence (TADF) emitters ( imCzDPS and imDPADPS ) that contain charged imidazolium groups tethered to the central luminophore were designed and synthesized as small molecule organic emitters for light-emitting e…

Highly luminescent perovskite–aluminum oxide composites

In this communication we report on the preparation of CH3NH3PbBr3 perovskite/Al2O3 nanoparticle composites in a thin film configuration and demonstrate their high photoluminescence quantum yield. The composite material is solution-processed at low temperature, using stable alumina nanoparticle dispersions. There is a large influence of the alumina nanoparticle concentration on the perovskite morphology and on its photoluminescence.

Efficient light-emitting electrochemical cells using small molecular weight, ionic, host-guest systems

This work has been supported by the Spanish Ministry of Economy and Competitiveness (MAT2014-55200). Light-emitting electrochemical cells (LECs) based on fluorescent host-guest small molecules system are reported. The LECs show electroluminescence coming solely from the guest, with an external quantum efficiency (EQE) of 2.0%, which is very close to the theoretical maximum EQE (2.2%) for this particular system. This work demonstrates the possibility to obtain high efficiency devices employing low-cost materials, making host-guest systems a real alternative to more traditional semiconducting polymer or transition metal compounds. Postprint Peer reviewed

Highly Stable and Efficient Light-Emitting Electrochemical Cells Based on Cationic Iridium Complexes Bearing Arylazole Ancillary Ligands.

A series of bis-cyclometalated iridium(III) complexes of general formula [Ir(ppy)2(N∧N)][PF6] (ppy− = 2-phenylpyridinate; N∧N = 2-(1H-imidazol-2-yl)pyridine (1), 2-(2-pyridyl)benzimidazole (2), 1-methyl-2-pyridin-2-yl- 1H-benzimidazole (3), 2-(4′-thiazolyl)benzimidazole (4), 1- methyl-2-(4′-thiazolyl)benzimidazole (5)) is reported, and their use as electroluminescent materials in light-emitting electrochemical cell (LEC) devices is investigated. [2][PF6] and [3][PF6] are orange emitters with intense unstructured emission around 590 nm in acetonitrile solution. [1][PF6], [4][PF6], and [5][PF6] are green weak emitters with structured emission bands peaking around 500 nm. The different photoph…

CCDC 1490702: Experimental Crystal Structure Determination

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CCDC 1423252: Experimental Crystal Structure Determination

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CCDC 987700: Experimental Crystal Structure Determination

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CCDC 1546695: Experimental Crystal Structure Determination

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CCDC 1422375: Experimental Crystal Structure Determination

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Enhancing the photoluminescence quantum yields of blue-emitting cationic iridium(III) complexes bearing bisphosphine ligands (dataset)

CCDC 1490703: Experimental Crystal Structure Determination

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CCDC 1423251: Experimental Crystal Structure Determination

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CCDC 974016: Experimental Crystal Structure Determination

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CCDC 974019: Experimental Crystal Structure Determination

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CCDC 1515402: Experimental Crystal Structure Determination

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CCDC 1490707: Experimental Crystal Structure Determination

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CCDC 1486906: Experimental Crystal Structure Determination

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CCDC 1422372: Experimental Crystal Structure Determination

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CCDC 1546696: Experimental Crystal Structure Determination

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CCDC 1486907: Experimental Crystal Structure Determination

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CCDC 1486908: Experimental Crystal Structure Determination

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CCDC 1844060: Experimental Crystal Structure Determination

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CCDC 1555727: Experimental Crystal Structure Determination

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CCDC 972526: Experimental Crystal Structure Determination

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CCDC 1423253: Experimental Crystal Structure Determination

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CCDC 1019228: Experimental Crystal Structure Determination

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CCDC 1581155: Experimental Crystal Structure Determination

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CCDC 1844063: Experimental Crystal Structure Determination

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Blue-Emitting Cationic Iridium(III) Complexes Featuring Pyridylpyrimidine Cyclometalating Ligands and their Use in Sky-Blue and Blue-Green Light-Emitting Electrochemical Cells (LEECs) and Organic Light-Emitting Diodes (OLEDs) (dataset)

CCDC 974020: Experimental Crystal Structure Determination

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CCDC 949190: Experimental Crystal Structure Determination

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CCDC 910854: Experimental Crystal Structure Determination

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CCDC 1423259: Experimental Crystal Structure Determination

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CCDC 1519073: Experimental Crystal Structure Determination

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CCDC 1490708: Experimental Crystal Structure Determination

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CCDC 1490705: Experimental Crystal Structure Determination

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CCDC 1429456: Experimental Crystal Structure Determination

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CCDC 1519074: Experimental Crystal Structure Determination

Related Article: Marta Martínez-Alonso, Jesús Cerdá, Cristina Momblona, Antonio Pertegás, José M. Junquera-Hernández, Aránzazu Heras, Ana M. Rodríguez, Gustavo Espino, Henk Bolink, and Enrique Ortí|2017|Inorg.Chem.|56|10298|doi:10.1021/acs.inorgchem.7b01167

CCDC 1546698: Experimental Crystal Structure Determination

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CCDC 1486911: Experimental Crystal Structure Determination

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CCDC 1019229: Experimental Crystal Structure Determination

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CCDC 1423255: Experimental Crystal Structure Determination

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CCDC 1515401: Experimental Crystal Structure Determination

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CCDC 1581154: Experimental Crystal Structure Determination

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CCDC 1538393: Experimental Crystal Structure Determination

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CCDC 1422374: Experimental Crystal Structure Determination

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CCDC 1538394: Experimental Crystal Structure Determination

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CCDC 1421913: Experimental Crystal Structure Determination

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CCDC 1581156: Experimental Crystal Structure Determination

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CCDC 1421914: Experimental Crystal Structure Determination

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CCDC 949192: Experimental Crystal Structure Determination

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CCDC 1019226: Experimental Crystal Structure Determination

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CCDC 1423254: Experimental Crystal Structure Determination

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CCDC 1581157: Experimental Crystal Structure Determination

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CCDC 974017: Experimental Crystal Structure Determination

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CCDC 974022: Experimental Crystal Structure Determination

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CCDC 974021: Experimental Crystal Structure Determination

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CCDC 1009455: Experimental Crystal Structure Determination

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CCDC 1055780: Experimental Crystal Structure Determination

Related Article: Cathrin D. Ertl, Jesús Cerdá, José M. Junquera-Hernández, Antonio Pertegás, Henk J. Bolink, Edwin C. Constable, Markus Neuburger, Enrique Ortí, Catherine E. Housecroft|2015|RSC Advances|5|42815|doi:10.1039/C5RA07940C

CCDC 1844062: Experimental Crystal Structure Determination

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Data underpinning - Chiral Iridium(III) Complexes in Light-Emitting Electrochemical Cells: Exploring The Impact of Stereochemistry on The Photophysical Properties and Device Performances

CCDC 974023: Experimental Crystal Structure Determination

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CCDC 1486909: Experimental Crystal Structure Determination

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CCDC 1421915: Experimental Crystal Structure Determination

Related Article: Cathrin D. Ertl, Lidón Gil-Escrig, Jesús Cerdá, Antonio Pertegás, Henk J. Bolink, José M. Junquera-Hernández, Alessandro Prescimone, Markus Neuburger, Edwin C. Constable, Enrique Ortí, Catherine E. Housecroft|2016|Dalton Trans.|45|11668|doi:10.1039/C6DT01325B

CCDC 949191: Experimental Crystal Structure Determination

Related Article: Andreas M. Bünzli, Henk J. Bolink, Edwin C. Constable, Catherine E. Housecroft, José M. Junquera-Hernández, Markus Neuburger, Enrique Ortí, Antonio Pertegás, Juan J. Serrano-Pérez, Daniel Tordera, Jennifer A. Zampese|2014|Dalton Trans.|43|738|doi:10.1039/C3DT52622D

CCDC 914725: Experimental Crystal Structure Determination

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CCDC 987698: Experimental Crystal Structure Determination

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