Synthesis of Anthracene Derivatives with Azaacene‐Containing Iptycene Wings and the Utilization as a Dopant for Solution‐Processed Organic Light‐Emitting Diodes

Abstract

Substituted acene derivatives are regarded as promising materials for organic electronic devices such as organicl ight-emitting diodes (OLEDs). In particular, anthracene derivatives are known to exhibit good fluorescence property,w ith the air stabilitya nd solubility in common organic solvents expectedt og ive advantages for solution-processed device fabrication.I nt his study,aseries of bistriisopropylsilyl(TIPS)ethynyla nthracened erivatives with azaacene-containing iptycene wings have been synthesized by using condensation reactions. Effects of size of azaacenes on opticalp roperties and packing structures were investigated.UV/Vis absorption and fluorescence spectra indicatet hat the p-elongation of iptycene units has small effects on the overall p-system,w hich is also supported by electrochemical measurements. Secondly,s ingle-crystal X-ray analysisi mplies that the molecules likely have interactions with the iptycene units of adjacent molecules,w hile the iptycene wings and TIPSethynyl groups can prevent the central anthracene unit from undesirable non-radiative energyl oss. Finally,t he most emissive derivative was used as ad opant for solution-pro-cessedO LEDs, showingo bvious electroluminescence with a luminance of over 920 cd m À2 .Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

Rational Molecular Design of Azaacene-Based Narrowband Green-Emitting Fluorophores: Modulation of Spectral Bandwidth and Vibronic Transitions

“…In this study, three distinct green-emitting fluorophores based on a fused azaacene moiety, 5s,16s-dihydro-5,16-[1,2]­benzenobenzo­[ b ]­naphtho­[2,3- i ]­phenazine (DBBNP), 5s,16s-dihydro-5,16-[1,2]­benzenobenzo­[ b ]­naphtho­[2,3- i ]­phenazine-7,14-dicarbonitrile (DBBNP2CN1), and 5s,16s-dihydro-5,16-[1,2]­benzenobenzo­[ b ]­naphtho­[2,3- i ]­phenazine-8,13-dicarbonitrile (DBBNP2CN2), were designed and synthesized by fine-modulating ICT interactions along the molecular backbone with variation in nitrile substitution positions. The structural rigidity based on the fully fused azaacene was considered to minimize the vibronic contribution (i.e., torsional rotation). − The terminal propeller type of the dibenzobarrelene moiety was expected to reduce intermolecular aggregation to minimize aggregation-caused quenching and excimer (or exciplex) formation . Furthermore, the detailed molecular structure–optical property relationships were investigated based on spectroscopic experimental results and theoretical calculations.…”

Polyazaacene and Cyclazaacene Precursors Synthesized by Dehydration Condensation from a Versatile Bis‐α‐diketone Unit Having an Anthracene Skeleton

“…[34,61] Since compound 1 possesses a versatile bis-α-diketone reaction site that facilitates numerous reactions, reactions with di/tetraamine derivatives generally produce high yields. [56] Compound 1 contains a mixture of two diastereomers (anti and syn) that differ in the orientation of BCOD units. Considering that only the syn-conformer contributes to the macrocyclic reaction, isolating the diastereomers of 1 is preferable.…”

“…Macrocyclic cyclazaacene compounds have rarely been reported to date [34,61] . Since compound 1 possesses a versatile bis‐ α ‐diketone reaction site that facilitates numerous reactions, reactions with di/tetraamine derivatives generally produce high yields [56] . Compound 1 contains a mixture of two diastereomers ( anti and syn ) that differ in the orientation of BCOD units.…”

Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

“…An increase of IP of azaacenes as compared to acenes leads to a significant improvement in their resistance against oxidative degradation, making the formation of carbonyl groups and/or degradative dimerization more difficult [ 30 ]. Azaacenes find their application as organic semiconductors not only in electronics but also in optoelectronics as electroluminophores in organic light emitting diodes (OLEDs) [ 31 , 32 , 33 , 34 ] and in photovoltaics as acceptors in non-fullerene organic photovoltaic cells [ 35 , 36 , 37 ].…”