Design and Synthesis of New Circularly Polarized Thermally Activated Delayed Fluorescence Emitters

Abstract

This work describes the first thermally activated delayed fluorescence material enabling circularly polarized light emission through chiral perturbation. These new molecular architectures obtained through a scalable one-pot sequential synthetic procedure at room temperature (83% yield) display high quantum yield (up to 74%) and circularly polarized luminescence with an absolute luminescence dissymmetry factor, |glum|, of 1.3 × 10−3. These chiral molecules have been used as an emissive dopant in an organic light emitting diode exhibiting external quantum efficiency as high as 9.1%.

Recent Advancements in and the Future of Organic Emitters: TADF‐ and RTP‐Active Multifunctional Organic Materials

“…Pieters and co-workers reported aD -A compound with an axially chiral tether, (R)-12 (Figure 37 a), which was readily synthesized from tetrafluoro dicyanobenzene, (R)-BINOL (1,1'-bi-2naphthol), andc arbazole in high yield as as ingle enantiomer. [114] In toluene, the compound exhibited at ypical CT absorptionb and and CT emission bands from l em = 486-573 nm, depending on the polarity of the solvent (Figure 37 c, e). The chiroptical spectra of the R and S enantiomers were clearly mirror images of each other (Figure 37 b,d), thusc onfirming that the installation of ac hiral orthogonal tether unit into the D-A system allowed for CPL.…”

Stimuli‐Responsive Circularly Polarized Organic Ultralong Room Temperature Phosphorescence

“…Circularly polarized luminescence (CPL) from organic fluorophores,phosphors,orsupramolecular systems has been af ocus of burgeoning research in recent years. [1][2][3][4][5][6] Exponential attention has been paid to the design and fabrication of novel CPL-featured organic optoelectronic materials including fluorescence organic luminophores, [7][8][9] thermally activated delayed fluorescence molecules, [10,11] and metal-organic phosphorescent complexes. [12] Ther ecent development of room temperature phosphorescence (RTP) of purely organic materials,e specially organic ultralong RTP( OURTP) with lifetimes over 100 ms [13][14][15][16][17][18] has significantly shaped the understanding of organic optoelectronics.…”

Computational simulation of vibrationally resolved spectra for spin‐forbidden transitions

“…Phosphorescent materials, particularly those containing transition metal complexes, have found application in several fields and have been the object of extensive studies in recent years, thanks in part to their applicability in electroluminescent devices such as organic light‐emitting diodes, sensors, and probes . In particular, chiral emitting systems are especially appealing because of their possible application in data storage, directional backlight 3D displays, and liquid crystal displays, as spin sources in optical spintronics and information carriers in quantum computing . Phosphorescence spectroscopy is the method of choice for the study of phosphorescent materials; however, the characterization of chiral systems would require a chiral spectroscopy, an example of which is circularly polarized luminescence, probing the differential emission of left and right circularly polarized light.…”

“…[1][2][3][4] In particular, chiral emitting systems are especially appealing because of their possible application in data storage, directional backlight 3D displays, and liquid crystal displays, as spin sources in optical spintronics and information carriers in quantum computing. [5][6][7][8][9][10][11][12] Phosphorescence spectroscopy is the method of choice for the study of phosphorescent materials; however, the characterization of chiral systems would require a chiral spectroscopy, an example of which is circularly polarized luminescence, probing the differential emission of left and right circularly polarized light. When associated to triplet-singlet transitions, this technique is also known as circularly polarized phosphorescence (CPP).…”