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Blue Thermally Activated Delayed Fluorescence from a Biphenyl Difluoroboron ?-Diketonate.

ABSTRACT: Optical properties of biphenyl difluoroboron ?-diketonates were studied in poly(lactic acid) (PLA) blends. Increased conjugation lowered the emission energy, decreased the singlet-triplet energy gap and yielded blue thermally activated delayed fluorescence (TADF). The properties of these biphenyl dyes may inform organic light emitting diode (OLED) and bioimaging agent design.

SUBMITTER: Daly ML

PROVIDER: S-EPMC5487001 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Blue Thermally Activated Delayed Fluorescence from a Biphenyl Difluoroboron β-Diketonate.

Daly Margaret L ML DeRosa Christopher A CA Kerr Caroline C Morris William A WA Fraser Cassandra L CL

RSC advances 20160830 85

Optical properties of biphenyl difluoroboron β-diketonates were studied in poly(lactic acid) (PLA) blends. Increased conjugation lowered the emission energy, decreased the singlet-triplet energy gap and yielded blue thermally activated delayed fluorescence (TADF). The properties of these biphenyl dyes may inform organic light emitting diode (OLED) and bioimaging agent design. ...[more]

PMID: 28670446

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High-Efficiency Diphenylpyrimidine Derivatives Blue Thermally Activated Delayed Fluorescence Organic Light-Emitting Diodes.

Project description:Organic light-emitting diodes with thermally activated delayed fluorescence emitter have been developed with highly twisted donor-acceptor configurations and color-pure blue emitters. Synthesized 4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)-10H-spiro[acridine-9,9'-fluorene] (4,6-PhPMAF) doped device with spiroacridine as a donor unit and diphenylpyrimidine as acceptor exhibits the device characteristics such as the luminescence, external quantum efficiencies, current efficiencies, and power efficiencies corresponding to 213 cd/m2, 2.95%, 3.27 cd/A, and 2.94 lm/W with Commission International de l'Eclairage (CIE) coordinates of (0.15, 0.11) in 4,6-PhPMAF-doped DPEPO emitter. The reported 10-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-10H-spiro[acridine-9,9'-fluorene] (2,6-PhPMAF) doped device exhibit high device performance with 1,445 cd/m2, 12.38%, 19.6 cd/A, and 15.4 lm/W, which might be originated from increased internal quantum efficiency by up-converted triplet excitons to the singlet state with relatively smaller ?E ST of 0.17 eV and higher reverse intersystem crossing rate (k RISC) of 1.0 ×108/s in 2,6-PhPMAF than 0.27 eV and 3.9 ×107/s in 4,6-PhPMAF. Despite low performance of 4,6-PhPMAF doped device, synthesized 4,6-PhPMAF has better color purity as a deep-blue emission with y axis (0.11) than reported 2,6-PhPMAF with y axis (0.19) in CIE coordinate. The synthesized 4,6-PhPMAF has higher thermal stability of any transition up to 300°C and decomposition temperature with only 5% weight loss in 400°C than reported 2,6-PhPMAF. The maximum photoluminescence emission of 4,6-PhPMAF in various solvents appeared at 438 nm, which has blue shift about 20 nm than that of 2,6-PhPMAF, which contributes deep-blue emission in synthesized 4,6-PhPMAF.

| S-EPMC7240071 | biostudies-literature

Luminescent Difluoroboron β-Diketonate PLA-PEG Nanoparticle.

Project description:Luminescent difluoroboron β-diketonate poly(lactic acid) (BF2bdkPLA) materials serve as biological imaging agents. In this study, dye structures were modified to achieve emission colors that span the visible region with potential for multiplexing applications. Four dyes with varying π-conjugation (phenyl, naphthyl) and donor groups (-OMe, -NMe2) were coupled to PLLA-PEG block copolymers (∼11 kDa) by a postpolymerization Mitsunobu reaction. The resulting dye-polymer conjugates were fabricated as nanoparticles (∼55 nm diameter) to produce nanomaterials with a range of emission colors (420-640 nm). For increased stability, dye-PLLA-PEG conjugates were also blended with dye-free PDLA-PEG to form stereocomplex nanoparticles of smaller size (∼45 nm diameter). The decreased dye loading in the stereoblocks blue-shifted the emission, generating a broader range of fluorescence colors (410-620 nm). Tumor accumulation was confirmed in a murine model through biodistribution studies with a red emitting dimethyl amino-substituted dye-polymer analogue. The synthesis, optical properties, oxygen-sensing capabilities, and stability of these block copolymer nanoparticles are presented.

| S-EPMC6348463 | biostudies-literature

Teaching an Old Poly(arylene ether) New Tricks: Efficient Blue Thermally Activated Delayed Fluorescence.

Project description:Polymer light-emitting diodes are attractive for optoelectronic applications owing to their brightness and ease of processing. However, often metals have to be inserted to increase the luminescence efficiency, and producing blue emitters is a challenge. Here we present a strategy to make blue thermally activated delayed fluorescence (TADF) polymers by directly embedding a small molecular blue TADF emitter into a poly(aryl ether) (PAE) backbone. Thanks to the oxygen-induced negligible electronic communication between neighboring TADF fragments, its corresponding blue delayed fluorescence can be inherited by the developed polymers. These polymers are free from metal catalyst contamination and show improved thermal stability. Through device optimization, a current efficiency of 29.7 cd/A (21.2 lm/W, 13.2%) is realized together with Commission Internationale de L'Eclairage coordinates of (0.18, 0.32). The value is competitive with blue phosphorescent polymers, highlighting the importance of the PAE backbone in achieving high-performance blue delayed fluorescence at a macromolecular level.

| S-EPMC6502736 | biostudies-literature

Pyrazine-Based Blue Thermally Activated Delayed Fluorescence Materials: Combine Small Singlet-Triplet Splitting With Large Fluorescence Rate.

Project description:Metal-free thermally activated delayed fluorescence (TADF) emitters have emerged as promising candidate materials for highly efficient and low-cost organic light-emitting diodes (OLEDs). Here, a novel acceptor 2-cyanopyrazine is selected for the construction of blue TADF molecules via computer-assisted molecular design. Both theoretical prediction and experimental photophysical data indicate a small S1-T1 energy gap (ΔE ST) and a relative large fluorescence rate (k F) in an o-phenylene-bridged 2-cyanopyrazine/3,6-di-tert-butylcarbazole compound (TCzPZCN). The k F value of 3.7 × 107 s-1 observed in a TCzPZCN doped film is among the highest in the TADF emitters with a ΔE ST smaller than 0.1 eV. Blue TADF emission is observed in a TCzPZCN doped film with a short TADF lifetime of 1.9 μs. The OLEDs using TCzPZCN as emitter exhibit a maximum external quantum efficiency (EQE) of 7.6% with low-efficiency roll-off. A sky-blue device containing a derivative of TCzPZCN achieves an improved EQE maximum of 12.2% by suppressing the non-radiative decay at T1.

| S-EPMC6536661 | biostudies-literature

Benzoate-based thermally activated delayed fluorescence materials.

Project description:Compounds PTZ-MBZ (methyl 3-(10H-phenothiazin-10-yl)benzoate) and DMAC-MBZ (methyl 3-(9,9-dimethylacridin-10(9H)-yl)benzoate) were conveniently synthesized, and they exhibited TADF properties with lifetimes of 0.80 and 2.17 μs, respectively. The spatially separated highest occupied molecular orbital and lowest unoccupied molecular orbital resulted in a very small singlet-triplet energy gap of 0.0152 eV and 0.0640 eV, respectively. Thermally activated delayed fluorescence materials with short lifetime could be used as promising luminescent materials for organic light-emitting diodes.

| S-EPMC10346356 | biostudies-literature

Optimizing the Intralayer and Interlayer Compatibility for High-Efficiency Blue Thermally Activated Delayed Fluorescence Diodes.

Project description:A series of phosphine oxide hosts, 4,6-bis(diphenylphosphoryl) dibenzothiophene (DBTDPO) and 4- diphenylphosphoryldibenzothiophene (DBTSPO), and electron transporting materials (ETM), 2-(diphenylphosphoryl)dibenzothiophene sulfone (2DBSOSPO), 3-(diphenylphosphoryl)dibenzothiophene sulfone (3DBSOSPO) and 4-(diphenylphosphoryl)dibenzothiophene sulfone (4DBSOSPO) were developed to support blue thermally activated delayed fluorescence (TADF) devices with high performance through optimizing intralayer and interlayer compatibility of emissive layers. On the basis of the triplet energy of ~3.0?eV for the hosts and ETMs, excitons can be effectively confined on DMAC-DPS. Compared to DBTSPO, DBTDPO can support the excellent distribution uniformity to blue TADF dye bis[4-(9,9-dimethyl-9,10-dihydroacridine) phenyl] sulfone (DMAC-DPS), owing to their configuration similarity; while 3DBSOSPO and 4DBSOSPO are superior in compatibility with the hosts due to the similar molecular polarity or configuration. Through adjusting the molecular configuration, the electrical performance of ETMs can be feasibly tuned, including the excellent electron mobility (?e) by the order of 10(-3)?cm(2)?V(-1)?s(-1). As the result, DBTDPO and 4DBSOSPO endowed their four-layer blue TADF devices with the maximum current efficiency of 33.5?cd A(-1) and the maximum external quantum efficiency more than 17%, which are impressive among the best blue TADF devices. It is showed that intralayer compatibility determines the maximum efficiencies, while interlayer compatibility influences efficiency stability.

| S-EPMC4731786 | biostudies-literature

Imidazole Acceptor for Both Vacuum-Processable and Solution-Processable Efficient Blue Thermally Activated Delayed Fluorescence.

Project description:The members of the imidazole family have been widely used for electron transporting, host, conventional fluorescent, and phosphorescent materials. Although the imidazole core also has great potential as an acceptor segment of deep-blue thermally activated delayed fluorescence (TADF) owing to its high triplet energy, the emission color of imidazole-based TADF organic light-emitting diodes (OLEDs) has so far been limited to blue to green. In this work, four acridan-imidazole systems are theoretically designed aiming for deep- or pure-blue emitters. All four emitters exhibit deep-blue to blue emission owing to the high energy levels of the lowest excited singlet states, exhibiting y coordinates of Commission Internationale de l'Eclairage coordinates between 0.06 and 0.26. The molecule composed of a trifluoromethyl-substituted benzimidazole acceptor in combination with a tetramethyl-9,10-dihydroacridine donor (named MAc-FBI) achieves a high maximum external quantum efficiency (EQEMAX) of 13.7% in its application to vacuum-processed OLEDs. The emitter has high solubility even in ecofriendly nonhalogenated solvents, which motivates us to fabricate solution-processed MAc-FBI-based OLEDs, resulting in an even higher EQEMAX of 16.1%.

| S-EPMC9118399 | biostudies-literature

High-performance blue OLED using multiresonance thermally activated delayed fluorescence host materials containing silicon atoms.

Project description:We report three highly efficient multiresonance thermally activated delayed fluorescence blue-emitter host materials that include 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene (DOBNA) and tetraphenylsilyl groups. The host materials doped with the conventional N7,N7,N13,N13,5,9,11,15-octaphenyl-5,9,11,15-tetrahydro-5,9,11,15-tetraaza-19b,20b-diboradinaphtho[3,2,1-de:1',2',3'-jk]pentacene-7,13-diamine (ν-DABNA) blue emitter exhibit a high photoluminescence quantum yield greater than 0.82, a high horizontal orientation greater than 88%, and a short photoluminescence decay time of 0.96-1.93 μs. Among devices fabricated using six synthesized compounds, the device with (4-(2,12-di-tert-butyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracen-7-yl)phenyl)triphenylsilane (TDBA-Si) shows high external quantum efficiency values of 36.2/35.0/31.3% at maximum luminance/500 cd m-2/1,000 cd m-2. This high performance is attributed to fast energy transfer from the host to the dopant. Other factors possibly contributing to the high performance are a T1 excited-state contribution, inhibition of aggregation by the bulky tetraphenylsilyl groups, high horizontal orientation, and high thermal stability. We achieve a high efficiency greater than 30% and a small roll-off value of 4.9% at 1,000 cd m-2 using the TDBA-Si host material.

| S-EPMC10495399 | biostudies-literature

Narrowband Deep-Blue Multi-Resonance Induced Thermally Activated Delayed Fluorescence: Insights from the Theoretical Molecular Design.

Project description:Multi-resonance thermal activated delayed fluorescence (MR-TADF) has been promising with large oscillator strength and narrow full width at half maxima of luminescence, overcoming the compromise of emission intensity and energy criteria of traditional charge transfer TADF frameworks. However, there are still limited theoretical investigations on the excitation mechanism and systematic molecular manipulation of MR-TADF structures. We systematically study the highly localized excitation (LE) characteristics based on typical blue boron-nitrogen (BN) MR-TADF emitters and prove the potential triangular core with theoretical approaches. A design strategy by extending the planar π-conjugate core structure is proposed to enhance the multiple resonance effects. Moreover, several substituted groups are introduced to the designed core, achieving color-tunable functions with relatively small energy split and strong oscillator strength simultaneously. This work provides a theoretical direction for molecular design strategy and a series of potential candidates for highly efficient BN MR-TADF emitters.

| S-EPMC8780697 | biostudies-literature

Highly efficient multi-resonance thermally activated delayed fluorescence material toward a BT.2020 deep-blue emitter.

Project description:An ultrapure deep-blue multi-resonance-induced thermally activated delayed fluorescence material (DOB2-DABNA-A) is designed and synthesized. Benefiting from a fully resonating extended helical π-conjugated system, this compound has a small ΔEST value of 3.6 meV and sufficient spin-orbit coupling to exhibit a high-rate constant for reverse intersystem crossing (kRISC = 1.1 × 106 s-1). Furthermore, an organic light-emitting diode employing DOB2-DABNA-A as an emitter is fabricated; it exhibits ultrapure deep-blue emission at 452 nm with a small full width at half maximum of 24 nm, corresponding to Commission Internationale de l'Éclairage (CIE) coordinates of (0.145, 0.049). The high kRISC value reduces the efficiency roll-off, resulting in a high external quantum efficiency (EQE) of 21.6% at 1000 cd m-2.

| S-EPMC10987657 | biostudies-literature

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