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Towards blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives.

ABSTRACT: Aiming to design blue fluorescent emitters with high photoluminescence quantum yields in solid-state, nitrogen-containing heteroaromatic 9,9-dimethylacridine was refined by tetraphenylethene and triphenylethene. Six tetra-/triphenylethene-substituted 9,9-dimethylacridines were synthesized by the Buchwald-Hartwig method with relatively high yields. Showing effects of substitution patterns, all emitters demonstrated high fluorescence quantum yields of 26-53% in non-doped films and 52-88% in doped films due to the aggregation induced/enhanced emission (AIE/AIEE) phenomena. In solid-state, the emitters emitted blue (451-481 nm) without doping and deep-blue (438-445 nm) with doping while greenish-yellow emission was detected for two compounds with additionally attached cyano-groups. The ionization potentials of the derivatives were found to be in the relatively wide range of 5.43-5.81 eV since cyano-groups were used in their design. Possible applications of the emitters were demonstrated in non-doped and doped organic light-emitting diodes with up to 2.3 % external quantum efficiencies for simple fluorescent devices. In the best case, deep-blue electroluminescence with chromaticity coordinates of (0.16, 0.10) was close to blue color standard (0.14, 0.08) of the National Television System Committee.

SUBMITTER: Cekaviciute M

PROVIDER: S-EPMC7037823 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Towards blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives.

Cekaviciute Monika M Petrauskaite Aina A Nasiri Sohrab S Simokaitiene Jurate J Volyniuk Dmytro D Sych Galyna G Budreckiene Ruta R Grazulevicius Juozas Vidas JV

Molecules (Basel, Switzerland) 20200121 3

Aiming to design blue fluorescent emitters with high photoluminescence quantum yields in solid-state, nitrogen-containing heteroaromatic 9,9-dimethylacridine was refined by tetraphenylethene and triphenylethene. Six tetra-/triphenylethene-substituted 9,9-dimethylacridines were synthesized by the Buchwald-Hartwig method with relatively high yields. Showing effects of substitution patterns, all emitters demonstrated high fluorescence quantum yields of 26-53% in non-doped films and 52-88% in doped ...[more]

PMID: 31973202

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Project description:IntroductionEvolution of organic light-emitting diodes (OLEDs) reached the point, which allows to obtain maximum internal quantum efficiency of 100% partly using heavy-metal-free emitters exhibiting thermally activated delayed fluorescence (TADF). Such emitters are also predictively perfect candidates for new generation of optical sensors since triplet harvesting can be sensitive to different analytes (at least to oxygen). Although many organic TADF emitters have been reported so far as OLED emitters, the investigation of materials suitable for both OLEDs and optical sensors remains extremely rare.ObjectivesAiming to achieve high photoluminescence quantum yields in solid-state and triplet harvesting abilities of organic semiconductors with efficient bipolar charge transport required for application in both blue OLEDs and optical sensors, symmetrical donor-acceptor-donor organic emitters containing pyrimidine-5-carbonitrile electron-withdrawing scaffold and carbazole, tert-butylcarbazole and methoxy carbazole donor moieties were designed, synthesized and investigated as the main objectives of this study.MethodsNew compounds were tested by many experimental methods including optical and photoelectron spectroscopy, time of flight technique, electrochemistry and thermal analyses.ResultsDemonstrating advantages of the molecular design, the synthesized emitters exhibited sky-blue efficient TADF with reverse intersystem crossing rates exceeding 106 s-1, aggregation-induced emission enhancement with photoluminescence quantum yields in solid state exceeding 50%, hole and electron transporting properties with charge mobilities exceeding 10-4 cm2/V·s, glass-forming properties with glass transition temperatures reaching 177 °C. Sky-blue OLEDs with non-doped light-emitting layers of the synthesized emitter showed maximum external efficiency of 12.8% while the doped device with the same emitter exhibited maximum external efficiency of 14%. The synthesized emitters were also used as oxygen probes for optical sensors with oxygen sensitivity estimated by the Stern-Volmer constant of 3.24·10-5 ppm-1.ConclusionThe developed bipolar TADF emitters with pyrimidine-5-carbonitrile and carbazole moieties showed effective applicability in both blue OLEDs and optical sensors.

Dataset Information

Towards blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives.

Publications

Towards blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives.

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