Chiral thermally activated delayed fluorescence materials for circularly polarized organic light-emitting diodes

Chirality is an important natural characteristic of organic molecules,and chiral organic molecules have shown extensive application in areas such as pharmaceutical development and material science.Benefiting from the ability to achieve circularly polarized luminescence(CPL),chiral luminescent materials have shown potential applications in anti-glare display,optical communication and,3D display,etc.Due to the ability to harvest both singlet and triplet excitons by a fast reverse intersystem crossing process without involving noble metals,chiral thermally activated delayed fluorescence(TADF)materials with point chirality,axial chirality,planar chirality and helical chirality are regarded as the state-of-the-art materials for circularly polarized organic light-emitting diodes(CP-OLEDs).In recent years,the chiral TADF materials and CP-OLEDs have rapidly developed,but unfortunately,the dissymmetry factors(g)are far from the requirement of practical applications.The ideal emitters and devices should have both high efficiency and a g factor,or at least a balance between these two elements.This review gives an overview of recent progress in chiral TADF materials,with a particular focus on the chiral skeleton,CPL property and device performance.Furthermore,the molecular design concept,device structure and methods to improve the g factors of chiral materials and CP-OLEDs are also discussed.

Color-tunable circularly polarized electroluminescence from a helical chiral multiple resonance emitter with B–N bonds

Chiral B,N-doped polycyclic aromatic hydrocarbons with circularly polarized luminescence(CPL) and small full-width at halfmaxima(FWHM) are promising multiple resonance(MR) emitters for CP organic light-emitting diodes(CP-OLEDs).This work presents a pair of chiral MR enantiomers,P/M-o[B-N]_(2)N_(2),featuring B–N bonds incorporated within a[7]-helicene skeleton.These enantiomers exhibit narrow 0-0 and 0-1 electronic transition bands,whose relative intensity can be fine-tuned by increasing doping concentrations,resulting in redshifts of the emission peak from 542 to 592 nm.The enantiomers show mirrorsymmetric CPL spectra with an asymmetry factor(|g_(PL)|) of 1.0×10^(-3).The hyperfluorescent CP-OLEDs with double-sensitized emitting layers display a FWHM of 33 nm,an external quantum efficiency of 25.1%,and a|g_(EL)|factor of 7.7×10^(-4).Notably,the CP-OLEDs realize color-tunable CP electroluminescence peak from 553 to 613 nm by regulating the vibrational coupling.This work provides a novel concept for the design of helical CP-MR materials and CP-OLEDs,highlighting their potential for future applications in advanced optoelectronic devices.

Frontiers in circularly polarized luminescence:molecular design,self-assembly,nanomaterials,and applications

The research in circularly polarized luminescence has attracted wide interest in recent years.Efforts on one side are directed toward the development of chiral materials with both high luminescence efficiency and dissymmetry factors,and on the other side,are focused on the exploitations of these materials in optoelectronic applications.This review summarizes the recent frontiers(mostly within five years)in the research in circularly polarized luminescence,including the development of chiral emissive materials based on organic small molecules,compounds with aggregation-induced emissions,supramolecular assemblies,liquid crystals and liquids,polymers,metal-ligand coordination complexes and assemblies,metal clusters,inorganic nanomaterials,and photon upconversion systems.In addition,recent applications of related materials in organic light-emitting devices,circularly polarized light detectors,and organic lasers and displays are also discussed.

Efficient circularly polarized photoluminescence and electroluminescence of chiral spiro-skeleton-based thermally activated delayed fluorescence molecules

Chiral thermally activated delayed fluorescence(TADF) molecules showing circularly polarized luminescence(CPL) have great potential in 3D displays. However, the relationships among CPL property, device performance and molecule structure are still not clear. In this article, we develop a strategy to promote dissymmetry factors without sacrifice in device performance and study the impact of molecule structures towards CPL property. Three novel TADF enantiomers are synthesized and studied.(R/S)-SCN with diminutive cyano group as an acceptor shows dissymmetry factor |gPL| ≈ 1.4×10^(-3) and noticeable organic light-emitting diode(OLED) performances with a maximum external quantum efficiency(EQEmax) of 23.0%. For(R/S)-SPHCN, the prolonged electron withdrawing group benzonitrile enhances |gPL| up to 3.6×10^(-3) with decreased device EQEmaxof 15.4%. By further replacing benzonitrile with(trifluoromethyl)pyridine, the enantiomers of(R/S)-SCFPY show similar |gPL| factors of 3.5×10^(-3) and device EQE_(max)up to 23.3%, which represents the highest efficiency among sprio-type TADF materials based OLEDs. Furthermore, the OLEDs also show obvious circularly polarized electroluminescence with gELfactors of-1.4/1.8×10^(-3),-3.6/3.6×10^(-3) and-3.7/3.6×10^(-3), respectively. These results indecate by delicate functional group engineering, high g factor can be achieved while maintaining decent device performances. Besides,(R/S)-SCFPY represents an impressive TADF emitter, which shows promoted g factor and recorded high device EQE_(max)among similar molecules.

Molecular self-induced configuration for improving dissymmetry factors in tetradentate platinum(Ⅱ) enantiomers cycloaddition

Two pairs of Pt(Ⅱ) enantiomers((RR)/(SS)-Py Pt,((RR)/(SS)-Py: N,N’-(1,2-diphenylethane-1,2-diyl)dipicolinamide;(RR)-P/M-QPt,((RR)/(SS)-Q: N,N’-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(quinoline-2-carboxamide)) were synthesized, respectively, with good circularly polarized luminescence(CPL) and tunable dissymmetry factors(g) by molecular self-induction with(RR)/(SS)-1,2-diphenylethane-1,2-diamine as carbon chiral sources. In the(RR)-P-QPt and(SS)-M-QPt, specific P-and M-configurations were effectively induced from intrinsic chiral carbon centres(R or S), ingeniously avoiding the racemic mixture formation and chiral separation. Furthermore, the chirality originating from both chiral carbon centres and helicene-like structure improves the g factor significantly, which provides a new molecular design strategy for chiral Pt(II) enantiomers with good CPL properties.

Cyclometallated iridium phosphors with amino acid ancillary ligand for intracellular imaging

Two new iridium complexes, （dfppy）2Ir（L-alanine） （dfppy-2-（2,4-difluorophenyl）pyridine） and （piq）21r（L-alanine） （piq - 1-phenylisoquinoline） were prepared with L-alanine as ancillary ligand. The two complexes show bright greenish-blue and red emission respectively. Theoretic study demonstrated that the emission nature of these complexes is mainly determined by the main ligand. And their improved aqueous solubility and the retained quantum yield favor their application in cell imaging. Intracellular imaging suggested that these two complexes have fine cell membrane permeability and is mainly distributed in cytoplasm. This study displayed a new strategy to design aqueous soluble phosphorescent cyclometallated if（Ⅲ） complex via introducing amino acid as ancillary ligand.

Recent Progress of Circularly Polarized Luminescence Materials from Chinese Perspectives

The research on circularly polarized luminescence(CPL)has garnered significant attention in recent years due to its many potential applications.One aspect of this research involves the pursuit of chiral materials that posess both high luminescence efficiency and dissymmetry factors.The investigation of CPL behavior is of paramount importance because the structural information of chiral luminescent systems in the excited state can be uncovered.The objective of this review is to offer a comprehensive overview of the latest advancements in the CPL research field,with a particular focus on the development of chiral emissive materials,including organic,inorganic,and hybrid substances.Furthermore,this review outlines the recent applications of these materials in areas such as displays,photoelectric devices,anticounterfeiting measures,and sensors.Finally,we highlight the primary challenges and potential prospects of CPL materials.Our aspiration is that this endeavor will contribute new perspectives and insights that further advancements in related research fields.