Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Phenoxazine-Dibenzothiophene Sulfoximine Emitters Featuring Both Thermally Activated Delayed Fluorescence and Aggregation Induced Emission.

ABSTRACT: In this work, we demonstrate dibenzothiophene sulfoximine derivatives as building blocks for constructing emitters featuring both thermally activated delayed fluorescent (TADF) and aggregation-induced emission (AIE) properties, with multiple advantages including high chemical and thermal stability, facile functionalization, as well as tunable electron-accepting ability. A series of phenoxazine-dibenzothiophene sulfoximine structured TADF emitters were successfully synthesized and their photophysical and electroluminescent properties were evaluated. The electroluminescence devices based on these emitters displayed diverse emissions from yellow to orange and reached external quantum efficiencies (EQEs) of 5.8% with 16.7% efficiency roll-off at a high brightness of 1000 cd·m-2.

SUBMITTER: Yang Y

PROVIDER: S-EPMC8434553 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Phenoxazine-Dibenzothiophene Sulfoximine Emitters Featuring Both Thermally Activated Delayed Fluorescence and Aggregation Induced Emission.

Yang Yiyu Y Xiao Ran R Cao Xiaosong X Chen Zhanxiang Z Lv Xialei X Zhang Youming Y Gong Shaolong S Zou Yang Y Yang Chuluo C

Molecules (Basel, Switzerland) 20210829 17

In this work, we demonstrate dibenzothiophene sulfoximine derivatives as building blocks for constructing emitters featuring both thermally activated delayed fluorescent (TADF) and aggregation-induced emission (AIE) properties, with multiple advantages including high chemical and thermal stability, facile functionalization, as well as tunable electron-accepting ability. A series of phenoxazine-dibenzothiophene sulfoximine structured TADF emitters were successfully synthesized and their photophys ...[more]

PMID: 34500677

Similar Datasets

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation.

Project description:Metal-free organic emitters with thermally activated delayed fluorescence (TADF) characteristics are emerging due to the potential applications in optoelectronic devices, time-resolved luminescence imaging, and solid-phase sensing. Herein, we synthesized two (4-bromobenzoyl)pyridine (BPy)-based donor-acceptor (D-A) compounds with varying donor size and strength: the emitter BPy-pTC with tert-butylcarbazole (TC) as the donor and BPy-p3C with bulky tricarbazole (3C) as the donor unit. Both BPy-pTC and BPy-p3C exhibited prominent emission with TADF properties in solution and in the solid phase. The stronger excited-state charge transfer was obtained for BPy-p3C due to the bulkier donor, leading to a more twisted D-A geometry than that of BPy-pTC. Hence, BPy-p3C exhibited aggregation-induced enhanced emission (AIEE) in a THF/water mixture. Interestingly, the singlet-triplet energy gap (ΔE ST) was reduced for both compounds in the aggregated state as compared to toluene solution. Consequently, a faster reverse intersystem crossing rate (k RISC) was obtained in the aggregated state, facilitating photon upconversion, leading to enhanced delayed fluorescence. Further, the lone-pair electrons of the pyridinyl nitrogen atom were found to be sensitive to acidic protons. Hence, the exposure to acid and base vapors using trifluoroacetic acid (TFA) and triethylamine (TEA) led to solid-phase fluorescence switching with fatigue resistance. The current study demonstrates the role of the donor strength and size in tuning ΔE ST in the aggregated state as well as the relevance for fluorescence-based acid-base sensing.

| S-EPMC9475190 | biostudies-literature

Rational Design of Highly Efficient Orange-Red/Red Thermally Activated Delayed Fluorescence Emitters with Submicrosecond Emission Lifetimes.

Project description:The development of orange-red/red thermally activated delayed fluorescence (TADF) materials with both high emission efficiencies and short lifetimes is highly desirable for electroluminescence (EL) applications, but remains a formidable challenge owing to the strict molecular design principles. Herein, two new orange-red/red TADF emitters, namely AC-PCNCF3 and TAC-PCNCF3, composed of pyridine-3,5-dicarbonitrile-derived electron-acceptor (PCNCF3) and acridine electron-donors (AC/TAC) are developed. These emitters in doped films exhibit excellent photophysical properties, including high photoluminescence quantum yields of up to 0.91, tiny singlet-triplet energy gaps of 0.01 eV, and ultrashort TADF lifetimes of less than 1 µs. The TADF-organic light-emitting diodes employing the AC-PCNCF3 as emitter achieve orange-red and red EL with high external quantum efficiencies of up to 25.0% and nearly 20% at doping concentrations of 5 and 40 wt%, respectively, both accompanied by well-suppressed efficiency roll-offs. This work provides an efficient molecular design strategy for developing high-performance red TADF materials.

| S-EPMC10427351 | biostudies-literature

Maximizing Chiral Perturbation on Thermally Activated Delayed Fluorescence Emitters and Elaboration of the First Top-Emission Circularly Polarized OLED.

Project description:Molecular designs merging circularly polarized luminescence (CPL) and thermally activated delayed fluorescence (CP-TADF) using the concept of chiral perturbation appeared recently as a cornerstone for the development of efficient CP-organic light emitting diodes (CP-OLED). Such devices could strongly increase the energy efficiency and performances of conventional OLED displays, in which 50% of the emitted light is often lost due to the use of antiglare filters. In this context, herein, ten couples of enantiomers derived from novel chiral emitter designs are reported, exhibiting CPL, TADF, and aggregation induced enhancement emission properties (AIEE). Representing the first structure properties relationship investigation for CP-TADF materials, this thorough experimental and theoretical work highlights crucial findings on the key structural and electronic parameters (isomerism, nature of the carbazole substituents) governing the synergy between CPL and TADF properties. To conclude this study, the first top emission CP-OLED is elaborated as a new approach of generating CP light in comparison with classical bottom-emission CP-OLED architecture. Indeed, the top-emission configuration represents the only relevant device architecture for future microdisplay applications. Thereby, in addition to offer molecular guidelines to combine efficiently TADF and CPL properties, this study opens new avenues toward practical applications for CP-OLEDs.

| S-EPMC8459798 | biostudies-literature

Persistent Dimer Emission in Thermally Activated Delayed Fluorescence Materials.

Project description:We expose significant changes in the emission color of carbazole-based thermally activated delayed fluorescence (TADF) emitters that arise from the presence of persistent dimer states in thin films and organic light-emitting diodes (OLEDs). Direct photoexcitation of this dimer state in 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) reveals the significant influence of dimer species on the color purity of its photoluminescence and electroluminescence. The dimer species is sensitive to the sample preparation method, and its enduring presence contributes to the widely reported concentration-mediated red shift in the photoluminescence and electroluminescence of evaporated thin films. This discovery has implications on the usability of these, and similar, molecules for OLEDs and explains disparate electroluminescence spectra presented in the literature for these compounds. The dimerization-controlled changes observed in the TADF process and photoluminescence efficiency mean that careful consideration of dimer states is imperative in the design of future TADF emitters and the interpretation of previously reported studies of carbazole-based TADF materials.

| S-EPMC6501699 | biostudies-literature

Dielectric control of reverse intersystem crossing in thermally activated delayed fluorescence emitters.

Project description:Thermally activated delayed fluorescence enables organic semiconductors with charge transfer-type excitons to convert dark triplet states into bright singlets via reverse intersystem crossing. However, thus far, the contribution from the dielectric environment has received insufficient attention. Here we study the role of the dielectric environment in a range of thermally activated delayed fluorescence materials with varying changes in dipole moment upon optical excitation. In dipolar emitters, we observe how environmental reorganization after excitation triggers the full charge transfer exciton formation, minimizing the singlet-triplet energy gap, with the emergence of two (reactant-inactive) modes acting as a vibrational fingerprint of the charge transfer product. In contrast, the dielectric environment plays a smaller role in less dipolar materials. The analysis of energy-time trajectories and their free-energy functions reveals that the dielectric environment substantially reduces the activation energy for reverse intersystem crossing in dipolar thermally activated delayed fluorescence emitters, increasing the reverse intersystem crossing rate by three orders of magnitude versus the isolated molecule.

| S-EPMC7613666 | biostudies-literature

Acceptor plane expansion enhances horizontal orientation of thermally activated delayed fluorescence emitters.

Project description:Manipulating orientation of organic emitters remains a formidable challenge in organic light-emitting diodes (OLEDs). Here, expansion of the acceptor plane of thermally activated delayed fluorescence (TADF) emitters was demonstrated to selectively modulate emitting dipole orientation. Two proof-of-the-concept molecules, PXZPyPM and PXZTAZPM, were prepared by introducing a planar 2-phenylpyridine or 2,4,6-triphenyl-1,3,5-triazine substituent into a prototypical molecule (PXZPM) bearing a pyrimidine core and two phenoxazine donors. This design approach suppressed the influence of substituents on electronic structures and associated optoelectronic properties. Accordingly, PXZPyPM and PXZTAZPM preserved almost the same excited states and similar emission characteristics as PXZPM. The expanded acceptor plane of PXZPyPM and PXZTAZPM resulted in a 15 to 18% increase in horizontal ratios of emitting dipole orientation. PXZPyPM supported its green device exhibiting an external quantum efficiency of 33.9% and a power efficiency of 118.9 lumen per watt, competitive with the most efficient green TADF OLEDs reported so far.

| S-EPMC7546701 | biostudies-literature

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells.

Project description:We designed and synthesized two new ionic thermally activated delayed fluorescent (TADF) emitters that are charged analogues of a known multiresonant TADF (MR-TADF) compound, DiKTa. The emission of the charged derivatives is red-shifted compared to the parent compound. For instance, DiKTa-OBuIm emits in the green (λPL = 499 nm, 1 wt % in mCP) while DiKTa-DPA-OBuIm emits in the red (λPL = 577 nm, 1 wt % in mCP). In 1 wt % mCP films, both emitters showed good photoluminescence quantum yields of 71% and 61%, and delayed lifetimes of 316.6 μs and 241.7 μs, respectively, for DiKTa-OBuIm and DiKTa-DPA-OBuIm, leading to reverse intersystem crossing rates of 2.85 × 103 s-1 and 3.04 × 103 s-1. Light-emitting electrochemical cells were prepared using both DiKTa-OBuIm and DiKTa-DPA-OBuIm as active emitters showing green (λmax = 534 nm) and red (λmax = 656 nm) emission, respectively.

| S-EPMC9520854 | biostudies-literature

Excited-State Modulation in Donor-Substituted Multiresonant Thermally Activated Delayed Fluorescence Emitters.

Project description:Strategies to tune the emission of multiresonant thermally activated delayed fluorescence (MR-TADF) emitters remain rare. Here, we explore the effect of donor substitution about a MR-TADF core on the emission energy and the nature of the excited state. We decorate different numbers and types of electron-donors about a central MR-TADF core, DiKTa. Depending on the identity and number of donor groups, the excited state either remains short-range charge transfer (SRCT) and thus characteristic of an MR-TADF emitter or becomes a long-range charge transfer (LRCT) that is typically observed in donor-acceptor TADF emitters. The impact is that in three examples that emit from a SRCT state, Cz-DiKTa, Cz-Ph-DiKTa, and 3Cz-DiKTa, the emission remains narrow, while in four examples that emit via a LRCT state, TMCz-DiKTa, DMAC-DiKTa, 3TMCz-DiKTa, and 3DMAC-DiKTa, the emission broadens significantly. Through this strategy, the organic light-emitting diodes fabricated with the three MR-TADF emitters show maximum electroluminescence emission wavelengths, λEL, of 511, 492, and 547 nm with moderate full width at half-maxima (fwhm) of 62, 61, and 54 nm, respectively. Importantly, each of these devices show high maximum external quantum efficiencies (EQEmax) of 24.4, 23.0, and 24.4%, which are among the highest reported with ketone-based MR-TADF emitters. OLEDs with D-A type emitters, DMAC-DiKTa and TMCz-DiKTa, also show high efficiencies, with EQEmax of 23.8 and 20.2%, but accompanied by broad emission at λEL of 549 and 527 nm, respectively. Notably, the DMAC-DiKTa-based OLED shows very small efficiency roll-off, and its EQE remains 18.5% at 1000 cd m-2. Therefore, this work demonstrates that manipulating the nature and numbers of donor groups decorating a central MR-TADF core is a promising strategy for both red-shifting the emission and improving the performance of the OLEDs.

| S-EPMC9121343 | biostudies-literature

Design and Synthesis of New Circularly Polarized Thermally Activated Delayed Fluorescence Emitters.

Project description:This work describes the first thermally activated delayed fluorescence material enabling circularly polarized light emission through chiral perturbation. These new molecular architectures obtained through a scalable one-pot sequential synthetic procedure at room temperature (83% yield) display high quantum yield (up to 74%) and circularly polarized luminescence with an absolute luminescence dissymmetry factor, |glum|, of 1.3 × 10(-3). These chiral molecules have been used as an emissive dopant in an organic light emitting diode exhibiting external quantum efficiency as high as 9.1%.

| S-EPMC5376272 | biostudies-literature

Asymmetric Thermally Activated Delayed Fluorescence Materials With Aggregation-Induced Emission for High-Efficiency Organic Light-Emitting Diodes.

Project description:The exploitation of thermally activated delayed fluorescence (TADF) emitters with aggregation-induced emission is highly prerequisite for the construction of highly efficient electroluminescent devices in materials science. Herein, two asymmetric TADF emitters of SFCOCz and SFCODPAC with charming aggregation-induced emission are expediently designed and prepared based on highly twisted strong electron-withdrawing acceptor (A) of sulfurafluorene (SF)-modified ketone (CO) and arylamine donor (D) in D1-A-D2 architecture by simple synthetic procedure in high yields. High photoluminescence quantum yields up to 73% and small singlet-triplet splitting of 0.03 eV; short exciton lifetimes are obtained in the resultant molecules. Strikingly, efficient non-doped and doped TADF organic light-emitting diodes (OLEDs) facilitated by these emitters show high luminance of 5,598 and 11,595 cd m-2, current efficiencies (CEs) of 16.8 and 35.6 cd/A, power efficiencies (PEs) of 9.1 and 29.8 lm/W, and external quantum efficiencies (EQEs) of 7.5 and 15.9%, respectively. This work furnishes a concrete instance in exploring efficient TADF emitter, which is highly conducive and encouraging in stimulating the development of TADF OLEDs with high brightness and excellent efficiencies simultaneously.

| S-EPMC7054483 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data