Organic triplet-state light-emitting materials (organic phosphorophores) have been one of the most important recent developments in the field of organic light-emitting diodes (OLEDs).[1±4] Organic electrophosphorescent materials provided one of the major breakthroughs in electroluminescence efficiency, which is usually limited to an external quantum efficiency (EQE) of around 5 % for devices based on singletstate fluorescent materials. Owing to its thin-film, lightweight, fast-response, wide-viewing-angle, high-contrast, and low-power attributes, OLEDs promise to be one of the major flat- [16±20]However, the development of highly efficient blue-light-emitting phosphorescent emitters in OLEDs, indispensable for the realization of RGB full-color displays and WOLEDs, is still in its infancy, and blue-light-emitting phosphorescent EL performance lags far behind that of the green-or red-light emitters.One of the best known triplet-state blue-light emitters is iridium(III) bis(4,6-difluorophenylpyridinato)picolate (FIrpic, Scheme 1).[21±23] Although a reasonably good EQE of about 10 % (or 10 lm W ±1 ) has been reported, its blue-light emission was far from saturated, with 1931 Commission Internationale de L'Eclairage x,y coordinates (CIE x,y ) of (0.17, 0.34) [23] thatwere best characterized as cyan in color. The most recent, and probably only the second phosphorescent blue emitter of practical use, was iridium(III) bis(4¢,6¢-difluorophenylpyridinato)tetrakis(1-pyrazolyl) borate) (FIr6), [24] whose blue OLED showed EQEs of 9±10 % (or 11±14 lm W ±1 ), and whose bluecolor chromaticity had been considerably improved to CIE x,y = 0.16, 0.26. There are a couple of limitations in the usage of phosphorescence-based materials for OLEDs. Compared with the short emission lifetime (scale of nanoseconds) of fluorescent materials, the relatively long phosphorescence lifetimes (microseconds scale) of the iridium complexes may lead to dominant triplet±triplet (T 1 ±T 1 ) annihilation at high currents. Long emission lifetimes also cause a long range of exciton diffusion (> 100 nm) that could get quenched in the adjacent layers of materials in the OLED. Consequently, organic phosphorescent materials are often adopted as dopants dispersed in a suitable host material, usually of high bandgap energies and good carrier transport properties. Arylamino-containing organic substances are usually the host materials of choice to alleviate this situation. This has worked reasonably well for phosphorescent green-or red-light-emitting materials. However, it has been demonstrated that the energy differences in the triplet energies of host and guest materials are very important for the confinement of electro-generated triplet excitons on the dopant molecules.[22±28] In cases of triplet-state bluelight emitters, common arylamino-containing substances, such as 4,4¢-bis(9-carbazolyl)-2,2¢-biphenyl (CBP) simply do not have sufficient triplet-state energy for effective T 1 ±T 1 energy transfer; later, a structurally modified host molecule, 1,3-bis(9-carba...
The excited-state intramolecular proton transfer (ESIPT) reaction in five-membered N-H...N hydrogen-bonding systems has been explored through design and syntheses of a series of 5-(2-pyridyl) 1-H-pyrazoles 1a-d. The ESIPT mechanism was confirmed through spectroscopy, relaxation dynamics, and corresponding methylated analogues. The results demonstrate for the first time a unique system among ESIPT molecules, in which ESIPT incorporates an appreciably large energy barrier fine-tuned by the skeletal reorganization. This makes 1a-d systems ideal models for probing the reaction potential energy surface.
Ir(III) metal complexes with formula [(nazo)2Ir(Fppz)] (1), [(nazo)2Ir(Bppz)] (2), and [(nazo)2Ir(Fptz)] (3) [(nazo)H = 4‐phenyl quinazoline, (Fppz)H = 3‐trifluoromethyl‐5‐(2‐pyridyl) pyrazole, (Bppz)H = 3‐t‐butyl‐5‐(2‐pyridyl) pyrazole, and (Fptz)H = 3‐trifluoromethyl‐5‐(2‐pyridyl) triazole] were synthesized, among which the exact configuration of 1 was confirmed using single‐crystal X‐ray diffraction analysis. These complexes exhibited bright red phosphorescence with relatively short lifetimes of 0.4–1.05 μs in both solution and the solid‐state at room temperature. Non‐doped organic light‐emitting diodes (OLEDs) were fabricated using complexes 1 and 2 in the absence of a host matrix. Saturated red electroluminescence was observed at λmax = 626 nm (host‐emitter complex 1) and 652 nm (host‐emitter complex 2), which corresponds to coordinates (0.66,0.34) and (0.69,0.31), respectively, on the 1931 Commission Internationale de l'Eclairage (CIE) chromaticity diagram. The non‐doped devices employing complex 1 showed electroluminance as high as 5780 cd m–2, an external quantum efficiency of 5.5 % at 8 V, and a current density of 20 mA cm–2. The short phosphorescence lifetime of 1 in the solid state, coupled with its modest π–π stacking interactions, appear to be the determining factors for its unusual success as a non‐doped host‐emitter.
A total of three distinctive main group and transition metal complexes containing the 2-pyridyl pyrazolate (pypz) ligand were prepared, namely, [B(C 6 F 5 ) 2 (pypz)] (1), [Ru(CO) 2 -(pypz) 2 ] (2), and [Os(CO) 2 (pypz) 2 ] (3), where (pypz)H ) 3-trifluoromethyl-5-(2-pyridyl)pyrazole. Single-crystal X-ray diffraction studies were carried out on complexes 2 and 3, revealing octahedral coordination geometry with two CO ligands located at cis dispositions. While the pypz ligand arrangement for complex 2 is in cis-(N py ,N py ) and trans-(N pz ,N pz ), complex 3 reveals a different configuration, cis-(N pz ,N pz ) and trans-(N py ,N py ) (N py for pyridine-N and N pz for pyrazolate donor sites). Similar to that of the in-situ-prepared pypz anion, the boron complex [B(C 6 F 5 ) 2 (pypz)] (1) exhibits a strong emission centered at 380 nm, which is unambiguously assigned to fluorescence derived from the S 1 (ππ*) f S 0 transition. In contrast to the nonluminescent behavior for Ru complex 2, the Os complex 3 displays unique, strong room-temperature phosphorescence, showing vibronic progressions at 430, 457, and 480 nm. The remarkable differences in photophysical properties were rationalized by a combination of π-electron accepting CO ligand, relative pypz orientation, and heavy-atom-enhanced spinorbit coupling effects.
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