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Journal ArticleDOI

Over 10% EQE Near-Infrared Electroluminescence Based on a Thermally Activated Delayed Fluorescence Emitter

01 Jul 2017-Advanced Functional Materials (John Wiley & Sons, Ltd)-Vol. 27, Iss: 26, pp 1700986
TL;DR: In this article, a wedge-shaped Dπ-A-π-D emitter with thermally activated delayed fluorescence property and a small single-triplet splitting (ΔEst) of 0.14 eV is presented.
Abstract: Significant effort has been made to develop novel material systems to improve the efficiency of near-infrared organic light-emitting diodes (NIR OLEDs). Of those, fluorescent chromophores are mostly studied because of their advantages in cost and tunability. However, it is still rare for fluorescent NIR emitters to present good color purities in the NIR range and to have high external quantum efficiency (EQE). Here, a wedge-shaped D-π-A-π-D emitter APDC-DTPA with thermally activated delayed fluorescence property and a small single-triplet splitting (ΔEst) of 0.14 eV is presented. The non-doped NIR device exhibits excellent performance with a maximum EQE of 2.19% and a peak wavelength of 777 nm. Remarkably, when 10 wt% of APDC-DTPA is doped in 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene host, an extremely high EQE of 10.19% with an emission peak of 693 nm is achieved. All these values represent the best result for NIR OLEDs based on a pure organic fluorescent emitter with similar device structure and color gamut.
Citations
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Journal ArticleDOI
TL;DR: In this paper, the authors reported thermally activated delayed fluorescent organic light-emitting diodes that operate at near-infrared wavelengths with a maximum external quantum efficiency of nearly 10% using a boron difluoride curcuminoid derivative.
Abstract: Near-infrared organic light-emitting diodes and semiconductor lasers could benefit a variety of applications including night-vision displays, sensors and information-secured displays. Organic dyes can generate electroluminescence efficiently at visible wavelengths, but organic light-emitting diodes are still underperforming in the near-infrared region. Here, we report thermally activated delayed fluorescent organic light-emitting diodes that operate at near-infrared wavelengths with a maximum external quantum efficiency of nearly 10% using a boron difluoride curcuminoid derivative. As well as an effective upconversion from triplet to singlet excited states due to the non-adiabatic coupling effect, this donor–acceptor–donor compound also exhibits efficient amplified spontaneous emission. By controlling the polarity of the active medium, the maximum emission wavelength of the electroluminescence spectrum can be tuned from 700 to 780 nm. This study represents an important advance in near-infrared organic light-emitting diodes and the design of alternative molecular architectures for photonic applications based on thermally activated delayed fluorescence. Near-infrared organic light-emitting diodes that operate in the 700 nm region with an external quantum efficiency of almost 10% are reported.

363 citations

Journal ArticleDOI
TL;DR: The useful principles and emerging structure–property relationships for precise molecular design toward AIEgens with desirable properties using concrete examples are revealed and their excellent performance in enabling new research directions in biomedical theranostics, optoelectronic devices, stimuli‐responsive smart materials, and visualization of physical processes are highlighted.
Abstract: Precise design of fluorescent molecules with desired properties has enabled the rapid development of many research fields. Among the different types of optically active materials, luminogens with aggregation-induced emission (AIEgens) have attracted significant interest over the past two decades. The negligible luminescence of AIEgens as a molecular species and high brightness in aggregate states distinguish them from conventional fluorescent dyes, which has galvanized efforts to bring AIEgens to a wide array of multidisciplinary applications. Herein, the useful principles and emerging structure-property relationships for precise molecular design toward AIEgens with desirable properties using concrete examples are revealed. The cutting-edge applications of AIEgens and their excellent performance in enabling new research directions in biomedical theranostics, optoelectronic devices, stimuli-responsive smart materials, and visualization of physical processes are also highlighted.

270 citations

Journal ArticleDOI
TL;DR: A strategy was developed to construct TADF organic solid films with strong DR or NIR emission feature and the high doped concentration and neat films exhibited efficient DR and NIR emissions, respectively.
Abstract: The design and synthesis of highly efficient deep red (DR) and near-infrared (NIR) organic emitting materials with characteristic of thermally activated delayed fluorescence (TADF) still remains a great challenge. A strategy was developed to construct TADF organic solid films with strong DR or NIR emission feature. The triphenylamine (TPA) and quinoxaline-6,7-dicarbonitrile (QCN) were employed as electron donor (D) and acceptor (A), respectively, to synthesize a TADF compound, TPA-QCN. The TPA-QCN molecule with orange-red emission in solution was employed as a dopant to prepare DR and NIR luminescent solid thin films. The high doped concentration and neat films exhibited efficient DR and NIR emissions, respectively. The highly efficient DR and NIR organic light-emitting devices (OLEDs) were fabricated by regulating TPA-QCN dopant concentration in the emitting layers.

257 citations

Journal ArticleDOI
TL;DR: A novel design strategy is reported for realizing highly efficient thermally activated delayed fluorescence materials via J-aggregates with strong intermolecular charge transfer (CT), which significantly decreases the energy gap between the lowest singlet and triplet excited states to induce high-efficiency TADF even in the NIR region.
Abstract: The development of high-efficiency and low-cost organic emissive materials and devices is intrinsically limited by the energy-gap law and spin statistics, especially in the near-infrared (NIR) region. A novel design strategy is reported for realizing highly efficient thermally activated delayed fluorescence (TADF) materials via J-aggregates with strong intermolecular charge transfer (CT). Two organic donor-acceptor molecules with strong and planar acceptor are designed and synthesized, which can readily form J-aggregates with strong intermolecular CT in solid states and exhibit wide-tuning emissions from yellow to NIR. Experimental and theoretical investigations expose that the formation of such J-aggregates mixes Frenkel excitons and CT excitons, which not only contributes to a fast radiative decay rate and a slow nonradiative decay rate for achieving nearly unity photoluminescence efficiency in solid films, but significantly decreases the energy gap between the lowest singlet and triplet excited states (≈0.3 eV) to induce high-efficiency TADF even in the NIR region. These organic light-emitting diodes exhibit external quantum efficiencies of 15.8% for red emission and 14.1% for NIR emission, which represent the best result for NIR organic light-emitting diodes (OLEDs) based on TADF materials. These findings open a new avenue for the development of high-efficiency organic emissive materials and devices based on molecular aggregates.

235 citations

References
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Journal ArticleDOI
13 Dec 2012-Nature
TL;DR: A class of metal-free organic electroluminescent molecules in which the energy gap between the singlet and triplet excited states is minimized by design, thereby promoting highly efficient spin up-conversion from non-radiative triplet states to radiative singlet states while maintaining high radiative decay rates.
Abstract: The inherent flexibility afforded by molecular design has accelerated the development of a wide variety of organic semiconductors over the past two decades. In particular, great advances have been made in the development of materials for organic light-emitting diodes (OLEDs), from early devices based on fluorescent molecules to those using phosphorescent molecules. In OLEDs, electrically injected charge carriers recombine to form singlet and triplet excitons in a 1:3 ratio; the use of phosphorescent metal-organic complexes exploits the normally non-radiative triplet excitons and so enhances the overall electroluminescence efficiency. Here we report a class of metal-free organic electroluminescent molecules in which the energy gap between the singlet and triplet excited states is minimized by design, thereby promoting highly efficient spin up-conversion from non-radiative triplet states to radiative singlet states while maintaining high radiative decay rates, of more than 10(6) decays per second. In other words, these molecules harness both singlet and triplet excitons for light emission through fluorescence decay channels, leading to an intrinsic fluorescence efficiency in excess of 90 per cent and a very high external electroluminescence efficiency, of more than 19 per cent, which is comparable to that achieved in high-efficiency phosphorescence-based OLEDs.

5,297 citations

Journal ArticleDOI
TL;DR: It is shown that a large delocalization of the highest occupied molecular orbital and lowest unoccupied molecular orbital in these charge-transfer compounds enhances the rate of radiative decay considerably by inducing a large oscillator strength even when there is a small overlap between the two wavefunctions.
Abstract: Organic compounds that exhibit highly efficient, stable blue emission are required to realize inexpensive organic light-emitting diodes for future displays and lighting applications. Here, we define the design rules for increasing the electroluminescence efficiency of blue-emitting organic molecules that exhibit thermally activated delayed fluorescence. We show that a large delocalization of the highest occupied molecular orbital and lowest unoccupied molecular orbital in these charge-transfer compounds enhances the rate of radiative decay considerably by inducing a large oscillator strength even when there is a small overlap between the two wavefunctions. A compound based on our design principles exhibited a high rate of fluorescence decay and efficient up-conversion of triplet excitons into singlet excited states, leading to both photoluminescence and internal electroluminescence quantum yields of nearly 100%.

1,007 citations

Journal ArticleDOI
TL;DR: Extremely efficient sky-blue organic electroluminescence with external quantum efficiency of ≈37% is achieved in a conventional planar device structure using a highly efficient thermally activated delayed fluorescence emitter based on the spiroacridine-triazine hybrid.
Abstract: Extremely efficient sky-blue organic electroluminescence with external quantum efficiency of ≈37% is achieved in a conventional planar device structure, using a highly efficient thermally activated delayed fluorescence emitter based on the spiroacridine-triazine hybrid and simultaneously possessing nearly unitary (100%) photoluminescence quantum yield, excellent thermal stability, and strongly horizontally oriented emitting dipoles (with a horizontal dipole ratio of 83%).

831 citations

Journal ArticleDOI
TL;DR: It is demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔE(ST) and large k(F), which is in good agreement with those predicted by corrected time-dependent density functional theory.
Abstract: Red fluorescent molecules suffer from large, non-radiative internal conversion rates (kIC) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (kF) as well as a small energy difference between the lowest singlet and triplet excited states (ΔEST) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔEST and large kF. Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The kF and ΔEST values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected tim...

750 citations

Journal ArticleDOI
TL;DR: This Focus Review describes the emerging class of near-infrared (NIR) organic compounds containing the conjugated polyene, polymethine, and donor-acceptor chromophores and exploration of their NIR-absorbing, Nir-fluorescence, and N IR-photosensitizing properties for potential applications in heat absorbers, solar cells, andNIR light-emitting diodes.
Abstract: This Focus Review describes the emerging class of near-infrared (NIR) organic compounds containing the conjugated polyene, polymethine, and donor-acceptor chromophores and exploration of their NIR-absorbing, NIR-fluorescence, and NIR-photosensitizing properties for potential applications in heat absorbers, solar cells, and NIR light-emitting diodes Examples of NIR organic compounds are reviewed with emphasis on the molecular design, NIR absorption, and fluorescence and particular emerging applications The donor-acceptor type of NIR chromophores are particularly introduced owing to some unique features, including the designer-made energy gaps, facile synthesis, good processability, and controllable morphology and properties in the solid state Future directions in research and development of NIR organic materials and applications are then offered from a personal perspective

637 citations

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