Polymorph acceptor-based triads with photoinduced TADF for UV sensing
Abstract In contrast to many donor–acceptor type organic luminophores exhibiting thermally activated delayed fluorescence (TADF), two deep blue TADF emitters designed in this work contain only typical electron accepting moieties with different electron accepting abilities. Derivatives of benzophenone and diphenylsulfone substituted with phenothiazine-5,5-dioxide donor moieties were synthesized and studied. In addition to the TADF, green to blue emission color switching and strong fluorescence intensity enhancement by more than 60 times was detected for THF solution of the derivative of phenothiazine-5,5-dioxide and benzophenone under increase of UV excitation dose. We proved by a variety of…
Structure–property relationship of isomeric diphenylethenyl-disubstituted dimethoxycarbazoles
Isomeric 3,6-dimethoxy- and 2,7-dimethoxycarbazoles containing diphenylethenyl moieties were synthesized by condensation of the appropriate dimethoxycarbazoles with diphenylacetaldehyde. The solid-state structures and the molecular order of the compounds were proven by X-ray crystallography. Both compounds were found to be capable of glass formation with comparable glass transition temperatures (70–71 °C). They exhibited high thermal stabilities, with the 5% weight loss temperatures exceeding 375 °C. The isomer having diphenylethenyl groups at C-3 and C-6 positions and methoxy groups at C-2 and C-7 positions (3a) exhibited aggregation-induced emission (AIE), while its counterpart having dip…
All-organic fast intersystem crossing assisted exciplexes exhibiting sub-microsecond thermally activated delayed fluorescence
A novel strategy is presented towards acquisition of exciplex systems exhibiting thermally activated delayed fluorescence (TADF) with a high reverse intersystem crossing (RISC) rate (exceeding 107 s−1). This approach involves constructing exciplex donor–acceptor molecular pairs, where the acceptor molecule possesses the ability to undergo fast and efficient intersystem crossing (ISC). With the use of 6-cyano-9-phenylpurine (PCP) acceptor and carbazole-based donor molecules, exciplexes were obtained, where the excitation is contained on PCP and undergoes fast ISC to form a local excited triplet state (3LEA). The controlled excitation transfer to the 3LEA level provides an optimal reverse int…
Bis(N-naphthyl-N-phenylamino)benzophenones as exciton-modulating materials for white TADF OLEDs with separated charge and exciton recombination zones
Abstract Organic semiconductors were employed as exciton modulators, blue emitters, hole-transporting materials and hosts with resonant-appropriate singlet and triplet energies for efficient and stable white organic light emitting diodes (OLEDs). Two 4,4'-bis(N-naphthyl-N-phenylamino)benzophenones were synthesized using isomeric N-naphthyl-N-phenylamines as the donors and benzophenone as the acceptor moiety. Molecular design of new compounds allowed to obtain required combination of properties, i.e. blue prompt fluorescence in solid state with singlet energies close to those of the selected blue emitter exhibiting thermally activated delayed fluorescence (TADF), low triplet energies of 2.32…
Pyrenyl substituted 1,8-naphthalimide as a new material for weak efficiency-roll-off red OLEDs: a theoretical and experimental study
Based on the theoretical calculations of excited states and semiconducting properties, a new 1,8-naphthalimide derivative having an electron-donating 1-pyrenyl group at the C-4 position was designed and synthesized. This derivative exhibited an excellent thermal stability and bipolar charge carrier transport ability. It was successfully utilized as a host in red phosphorescent organic light-emitting diodes showing an efficient energy transfer from the host to the phosphorescent emitter. The derivative may be a single material electroplex-forming host for PhOLEDs. The best fabricated red emitting device demonstrated maximum current, power, and external quantum efficiencies of 10.8 cd A−1, 7 …
Derivatives of indandione and differently substituted triphenylamine with charge-transporting and NLO properties
Abstract Derivatives containing electron-donaiting triphenylamino groups and electron-withdrawing indandione moieties were synthesized and their thermal, electrochemical, photoelectrical and nonlinear optical properties were studied. The synthesized compounds form glasses with the glass transition temperatures ranging from 69 to 118 °C. The ionization potentials of the solid samples of the synthesized materials were found to be in the range of 5.48–5.69 eV. Hole-drift mobilities estimated by xerographic time of flight technique in the amorphous layers of 2-({4-[(4-{[(2E)-1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene]methyl}phenyl)(4-methoxyphenyl)amino]phenyl}methylidene)-2,3-dihydro-1H-indene-1…
Effect of donor substituents on thermally activated delayed fluorescence of diphenylsulfone derivatives
This research was funded by the European Social Fund according to the activity ‘Improvement of researchers’ qualification by implementing world-class R&D projects’ of Measure No. 09.3.3-LMT-K-712. DG acknowledges to the ERDF PostDoc project No. 1.1.1.2/VIAA/1/16/177;
Donor and acceptor substituted triphenylamines exhibiting bipolar charge-transporting and NLO properties
Donor-acceptor type triphenylamine-based malonodinitriles were synthesized and their thermal, optical, photophysical, electrochemical and nonlinear optical properties were studied. The synthesized compounds formed glasses with the glass transition temperatures ranging from 38 to 107 °C. The ionization potentials of the samples of the compounds established by cyclic voltammetry were found to be in the range of 5.50–5.57 eV, while those estimated by photoelectron emission spectrometry ranged from 5.36 to 5.74 eV. The electron affinity values of the compounds were found to be in the range of −3.41–−3.05 eV. The ambipolar charge-transporting properties were observed for the layers of triphenyla…
HAPPY Dyes as Light Amplification Media in Thin Films
A series of 1Hamorphous tri-phenyl pyridine (HAPPY) dyes have been synthesized from luminescent triphenyl-group-containing 2-methyl-6-styryl-substituted-4H-pyran-4-ylidene derivatives in reactions with benzylamine and investigated for suitability as solution-processable light-emitting medium components in thin films for amplified spontaneous emission (ASE). Conversion of a 4H-pyrane ring into a 1H-pyridine fragment enables aggregation-induced emission enhancement (AIEE) behavior in the target products and slightly increases thermal stability, glass transition temperatures, and ASE efficiency with PLQY up to 15% and ASE thresholds as low as 46 μJ/cm2 in neat spin-cast films, although thermal…
Differently substituted benzonitriles for non-doped OLEDs
DG acknowledges to the ERDF PostDoc grant No. 1.1.1.2/VIAA/1/16/177 . This research was funded by the European Regional Development Fund according to the supported activity ‘Research Projects Implemented by World-class Researcher Groups’ under Measure No. 01.2.2-LMT-K-718 .
Diphenylsulfone-based hosts for electroluminescent devices: Effect of donor substituents
DG acknowledges to the ERDF PostDoc project No. 1.1.1.2/VIAA/1/16/177. This work was supported by the project of scientific co-operation program between Latvia, Lithuania and Taiwan ?Polymeric Emitters with Controllable Thermally Activated Delayed Fluorescence for Solution-processable OLEDs? (grant No. S-LLT-19-4). Support of the Lithuanian Academy of Sciences is gratefully acknowledged; Institute of Solid State Physics, University of Latvia as the Center of Excellence has received funding from the European Union’s Horizon 2020 Framework Programme H2020-WIDESPREAD-01-2016-2017-TeamingPhase2 under grant agreement No. 739508, project CAMART²
Flexible diphenylsulfone versus rigid dibenzothiophene-dioxide as acceptor moieties in donor-acceptor-donor TADF emitters for highly efficient OLEDs
DG acknowledges funding from the ERDF PostDoc project No. 1.1.1.2/VIAA/1/16/177 . This research is/was funded by the European Regional Development Fund according to the supported activity ‘ Research Projects Implemented by World-class Researcher Groups ’ under Measure No. 01.2.2-LMT-K-718 . Ministry of Science and Technology (MOST), Taiwan , Grant No. MOST 106-2923-E-155-002-MY3 . This work was also supported by the Ministry of Education and Science of Ukraine (projects no. 0117U003908 and 0118U003862 ), and by the Olle Engkvist Byggmästare foundation (contract No. 189-0223 ). The quantum-chemical calculations were performed with computational resources provided by the High Performance Comp…
Methoxycarbazolyl-disubstituted dibenzofuranes as holes- and electrons-transporting hosts for phosphorescent and TADF-based OLEDs
This research was funded by European Social Fund (Project No 09.3.3-LMT-K-712-02-0105). DG acknowledges to the ERDF PostDoc grant No. 1.1.1.2/VIAA/1/16/177.
Multifunctional derivatives of dimethoxy-substituted triphenylamine containing different acceptor moieties
This project has received funding from the Research Council of Lithuania (LMTLT), Agreement No. [S-LZ-19-2]. This research was funded by the Région Centre, the Tunisian ministry of research, University of Monastir and the French ministry of Higher Education and Research. J. Bouclé would like to thank the Sigma-Lim LabEx environment for financial supports, and the PLATINOM facility at XLIM laboratory regarding device fabrication and characterizations. DG acknowledges the Lithuanian Academy of Sciences for the financial support.
CCDC 1830576: Experimental Crystal Structure Determination
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CCDC 1988182: Experimental Crystal Structure Determination
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