Ultrapure blue-fluorescent molecules based on thermally activated delayed fluorescence are developed. Organic light-emitting diode (OLED) devices employing the new emitters exhibit a deep blue emission at 467 nm with full-width half-maximum of 28 nm, CIE coordinates (0.12, 0.13), and an internal quantum efficiency ≈100%, which represent record-setting performance for OLED devices.

The development of a one-step borylation 1,3-diaryloxybenzenes, yielding novel boron-containing polycyclic aromatic compounds, is reported. resulting compounds possess high singlet-triplet excitation energies as result localized frontier molecular orbitals induced by boron and oxygen. Using these host material, we successfully prepared phosphorescent organic light-emitting diodes exhibiting efficiency adequate lifetimes. Moreover, using the present borylation, succeeded in synthesis an...

An expanded heterohelicene consisting of three BN2-embedded [4]helicene subunits (V-DABNA-Mes) has been synthesized by one-shot triple borylation. The key to success is the excessive use boron tribromide in an autoclave. Based on multiple resonance effect and six nitrogen atoms, V-DABNA-Mes exhibited a narrowband sky-blue thermally activated delayed fluorescence with full width at half-maximum 16 nm. resonating π-extension minimized singlet-triplet energy gap enabled rapid reverse...

Novel boron-fused double [5]helicenes were synthesized from hexabromobenzene in two steps via Hart reaction and demethylative cyclization. The parent helicene shows excellent ambipolar conductivity, which can be explained by unique 3D π-stacking with a brickwork arrangement. Moreover, the introduction of four tert-butyl groups suppresses racemization, enabling optical resolution. enantiomerically pure deep blue fluorescence Commission Internationale de l'Eclairage coordinates (0.15, 0.08)...

High-resolution atomic force microscopy can resolve the difference among B, C, and N atoms.

Abstract The increasing attention devoted to triangulenes and their heteroatom derivatives inspired us explore a divergent synthesis of heteroatom‐centered 4,8,12‐triazatriangulenes, which involved the preparation nitrogen‐containing macrocyclic precursor subsequent central introduction by electrophilic C−Li C−H substitution. boron‐centered triangulene has planar structure unlike bowl‐shaped phosphorus‐ silicon‐centered triangulenes. described synthetic procedure can be used fabricate broad...

In this work, we achieved the triplet-energy control of polycyclic aromatic hydrocarbons (PAHs) by replacing Carbon−Carbon (CC) unit with a Boron−Nitrogen (BN) unit. Time-dependent density functional theory calculations suggested that insertion BN may cause localization singly occupied molecular orbitals 1 and 2 (SOMO1/SOMO2) in triplet state, which turn can reduce exchange interaction dramatically increase high singlet–triplet excitation energy (ET). The PAH containing unit,...

A corannulene possessing two B-N units on the spoke, 10b1,18b1-diaza-10b,18b-diboratetrabenzo [ a, g, j, m]corannulene, was synthesized a multigram scale in four steps from commercially available compounds. Its shallow bowl-shaped structure confirmed by X-ray crystallography. The B2N2-embedded showed strong blue fluorescence and employed as an efficient emitter for organic light-emitting diode.

Abstract A P‐fused double helicene consisting of a highly distorted benzene ring, with bending angle 23°, has been synthesized by tandem intramolecular phospha‐Friedel–Crafts reaction. Despite the distortion and reduced aromaticity, shows thermal chemical stability. These are important features that make these compounds attractive for applications as new C 2 ‐symmetric bisphosphine ligand. The simple strategy proposed in this work can be used to prepare diverse range molecules.

Tandem intramolecular electrophilic arene borylation was developed to facilitate access B-doped polycyclic aromatic hydrocarbons (PAHs). DFT calculations revealed that occurred via a four-membered ring transition state, in which C–B and H–Br bonds formed concerted manner. An organic light-emitting diode employing the PAH as an emitter PAH-based field-effect transistor were successfully fabricated, demonstrating potential of PAHs materials science.

Abstract A demethylative direct borylation is reported, which was applied to the synthesis of benzo[ fg ]tetracenes containing boronate ester, amide, and thioester substructures. Depending on heteroatom adjacent boron, molecules showed characteristic photophysical properties, molecular arrangements, chemical stabilities. The key successful appropriate choice boron source Brønsted base. versatility demonstrated by a boronate‐based hi ]hexacene.

Abstract The development of a one‐step borylation 1,3‐diaryloxybenzenes, yielding novel boron‐containing polycyclic aromatic compounds, is reported. resulting compounds possess high singlet‐triplet excitation energies as result localized frontier molecular orbitals induced by boron and oxygen. Using these host material, we successfully prepared phosphorescent organic light‐emitting diodes exhibiting efficiency adequate lifetimes. Moreover, using the present borylation, succeeded in synthesis...

Boraphenalenes, compounds in which one carbon atom the phenalenyl skeleton is replaced with a boron atom, have attracted attention for their solid-state and electronic structures; however, construction of boraphenalene skeletons remains challenging because lack suitable methods. Through this study, we showed that tandem borylative cyclization C3-symmetric dehydrobenzo[12]annulenes produces new class fully fused boron-atom-embedded polycyclic hydrocarbons possessing 9b-boraphenalene skeleton....

Abstract The increasing attention devoted to triangulenes and their heteroatom derivatives inspired us explore a divergent synthesis of heteroatom‐centered 4,8,12‐triazatriangulenes, which involved the preparation nitrogen‐containing macrocyclic precursor subsequent central introduction by electrophilic C−Li C−H substitution. boron‐centered triangulene has planar structure unlike bowl‐shaped phosphorus‐ silicon‐centered triangulenes. described synthetic procedure can be used fabricate broad...

Abstract A triphosphaazatriangulene (H 3 L) was synthesized through an intramolecular triple phospha‐Friedel–Crafts reaction. The H L triangulene contains three phosphinate groups and extended π‐conjugated framework, which enables the stimuli‐responsive reversible transformation of [Cu(HL)(DMSO)⋅(MeOH)] n , a 3D‐MOF that exhibits sorption characteristics, into L⋅0.5 [Cu 2 (OH) 4 ⋅6 O] ⋅4 O), 1D‐columnar assembled proton‐conducting material. hydrophilic nature latter resulted in proton...

Abstract Cationic BN‐embedded polycyclic aromatic hydrocarbons (BN‐PAH + s) were synthesized from a nitrogen‐containing macrocycle via pyridine‐directed tandem C−H borylation. Incorporating BN into PAH resulted in remarkable hypsochromic shift due to an increase the LUMO energy and symmetry changes of HOMO LUMO. Electrophilic substitution or anion exchange BN‐PAH possessing tetrabromoborate as counter ( [BBr 4 − ] ) afforded air‐stable BN‐PAH/PAH s. Of these, [TfO allowed reversible...

Abstract A P‐fused double helicene consisting of a highly distorted benzene ring, with bending angle 23°, has been synthesized by tandem intramolecular phospha‐Friedel–Crafts reaction. Despite the distortion and reduced aromaticity, shows thermal chemical stability. These are important features that make these compounds attractive for applications as new C 2 ‐symmetric bisphosphine ligand. The simple strategy proposed in this work can be used to prepare diverse range molecules.

Abstract Organic light‐emitting diodes (OLEDs) receive considerable attention because of their commercial use in flat panel displays. Herein, highly efficient spiroborate‐based host materials are reported for blue OLEDs. Our designed spiroborates ( SBOX ) were simple to synthesize and exhibited high triplet excitation energies, narrow S‐T gaps, balanced charge carrier mobilities. A OLED containing one the spiroborates, SBON , as a external quantum efficiency (27.6 %) low turn‐on voltage (3.7...

Abstract Cationic BN‐embedded polycyclic aromatic hydrocarbons (BN‐PAH + s) were synthesized from a nitrogen‐containing macrocycle via pyridine‐directed tandem C−H borylation. Incorporating BN into PAH resulted in remarkable hypsochromic shift due to an increase the LUMO energy and symmetry changes of HOMO LUMO. Electrophilic substitution or anion exchange BN‐PAH possessing tetrabromoborate as counter ( [BBr 4 − ] ) afforded air‐stable BN‐PAH/PAH s. Of these, [TfO allowed reversible...

We report a short synthesis of phosphorus-fused triarylphosphine oxides, 5,9-dioxa-13b-oxophosphanaphtho[3,2,1-de]anthracenes (DOPNAs), based on tandem phospha-Friedel–Crafts reaction. Phosphorescence, UV–visible absorption, and photoelectron yield spectroscopy vacuum-deposited thin films revealed that the triplet energies, optical band gaps, ionization potentials these materials were sufficiently large for them to be utilized in organic light-emitting diodes (OLEDs). Therefore, we...

Phosphorus-centered 4,8,12-triazatriangulene was identified as an efficient exciton blocking material for phosphorescent organic light-emitting diodes (PHOLEDs). The external quantum efficiency values of Ir(ppy)3-based green PHOLEDs were greatly improved to 20% at 1000 cd m−2.

Abstract Organic light‐emitting diodes (OLEDs) receive considerable attention because of their commercial use in flat panel displays. Herein, highly efficient spiroborate‐based host materials are reported for blue OLEDs. Our designed spiroborates ( SBOX ) were simple to synthesize and exhibited high triplet excitation energies, narrow S‐T gaps, balanced charge carrier mobilities. A OLED containing one the spiroborates, SBON , as a external quantum efficiency (27.6 %) low turn‐on voltage (3.7...

Abstract A triphosphaazatriangulene (H 3 L) was synthesized through an intramolecular triple phospha‐Friedel–Crafts reaction. The H L triangulene contains three phosphinate groups and extended π‐conjugated framework, which enables the stimuli‐responsive reversible transformation of [Cu(HL)(DMSO)⋅(MeOH)] n , a 3D‐MOF that exhibits sorption characteristics, into L⋅0.5 [Cu 2 (OH) 4 ⋅6 O] ⋅4 O), 1D‐columnar assembled proton‐conducting material. hydrophilic nature latter resulted in proton...

Designing the reactant molecule of an initial reaction, based on quantum chemical pathway exploration, enabled us to access a new i.e., tetraborylation reaction