Acridone and quinacridone derivatives with carbazole or phenoxazine substituents: synthesis, electrochemistry, photophysics and application as TADF electroluminophores

Six acridone (quinacridone) derivatives containing either carbazole or phenoxazine substituents were designed and synthesized with the aim of elucidating the effect of the donor (D) and acceptor (A) linking pattern (D-A, D-A-D or D-π-A-π-D) on their photophysical and electrochemical properties. Thes...

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Bibliographic Details
Published in:Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2022-09, Vol.1 (34), p.12377-12391
Main Authors: Kulszewicz-Bajer, Irena, Guzauskas, Matas, Makowska-Janusik, Ma gorzata, Zagórska, Ma gorzata, Mahmoudi, Malek, Grazulevicius, Juozas V, Pro, Adam, Volyniuk, Dmytro
Format: Article
Language:English
Subjects:
Agglomeration
Carbazoles
Electric fields
Electrochemical analysis
Electrochemical oxidation
Electrochemistry
Fluorescence
Hole mobility
Ionization potentials
Mathematical analysis
Molecular structure
Optical properties
Optoelectronics
Photoluminescence
Spectral emittance
Toluene
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Summary:Six acridone (quinacridone) derivatives containing either carbazole or phenoxazine substituents were designed and synthesized with the aim of elucidating the effect of the donor (D) and acceptor (A) linking pattern (D-A, D-A-D or D-π-A-π-D) on their photophysical and electrochemical properties. These new electroactive compounds combine reversible electrochemical oxidation with excellent luminescent properties. Their electrochemically determined ionization potentials (IPs) are in the range from 5.09 eV to 5.45 eV, higher for derivatives with carbazole donors as compared to phenoxazine ones. The measured electron affinities (EAs) are in the range from −2.53 eV to −2.64 eV with the exception of the quinacridone derivative showing EA of −3.03 eV. Their vacuum-deposited films emit radiation in a wide spectral range from sky-blue to red. Compounds with carbazole moieties (compounds 1 , 2 and 6 in the subsequent text) showed prompt fluorescence and aggregation-caused quenching. Photoluminescent quantum yields (PLQYs) of their toluene solutions reached values up to 69%. Compounds containing phenoxazine moieties (compounds marked as 3-5 ) demonstrated thermally activated delayed fluorescence (TADF) and aggregation-induced emission enhancement (AIEE). Their neat films showed PLQYs of 35%. Quinacridone disubstituted with carbazole (compound 6 ) showed the highest hole mobility reaching 2.53 × 10 −3 cm 2 V −1 s −1 at electric field of 3.6 × 10 5 V cm −1 . Carbazolyl disubstituted acridone (compound 2 ) and phenoxazinyl monosubstituted acridone (compound 3 ) turned out to be ambipolar compounds showing reasonably balanced electron and hole mobilities. The appropriate combination of redox, transport and luminescent properties makes the studied compounds suitable candidates for optoelectronic applications. Test OLEDs fabricated from 3 exhibited maximum external quantum efficiencies reaching 16.7%. Finally, an excellent agreement between the experimental results and those obtained by DFT calculations should be stressed. The basics for selection according to the user needs of either D-A, D-A-D or D-π-A-π-D types of molecular structures of TADF/AIEE luminophores are provided in this study. Six acridone (quinacridone) derivatives containing either carbazole or phenoxazine substituents were synthesized aiming to elucidate the effect of the donor and acceptor linking pattern on their photophysical and electrochemical properties.
ISSN:2050-7526
2050-7534
DOI:10.1039/d2tc02270b