Highly efficient blue thermally activated delayed fluorescence emitters based on symmetrical and rigid oxygen-bridged boron acceptors

Materials that exhibit thermally activated delayed fluorescence are promising for the realization of efficient organic light-emitting diodes. However, finding suitable deep-blue thermally activated delayed fluorescence materials is still challenging. Here, we report two highly efficient deep-blue thermally activated delayed fluorescence emitters, TDBA–Ac and TDBA–DI, containing oxygen-bridged, symmetric and rigid boron acceptor moieties. Both emitters have been designed to have high photoluminescence quantum yield and narrow-band blue emission. TDBA–Ac and TDBA–DI exhibited deep-blue emission and a small singlet–triplet energy gap of 0.06 eV and 0.11 eV, respectively, in toluene. The 20wt%-doped films of TDBA–Ac and TDBA–DI in DBFPO host exhibited high photoluminescence quantum yields of 93% and 99%, respectively. The fabricated TDBA–DI device showed an extremely high external quantum efficiency of 38.15 ± 0.42% in the blue region with low roll-off characteristics of 25.2% at high luminance of up to 5,000 cd m–2. The TDBA–Ac-doped device exhibited a high external quantum efficiency of 21.50 ± 0.22% with deep-blue colour coordinates of (0.15, 0.06).The discovery of two deep-blue organic emitters of light could aid the development of next-generation organic light-emitting devices.

[1]  Yong Joo Cho,et al.  Molecular Design Strategy of Organic Thermally Activated Delayed Fluorescence Emitters , 2017 .

[2]  Effect of various host characteristics on blue thermally activated delayed fluorescent devices , 2018, Organic Electronics.

[3]  Lei Zhang,et al.  Thermally Activated Delayed Fluorescence Materials Towards the Breakthrough of Organoelectronics , 2014, Advanced materials.

[4]  C. Adachi,et al.  Controlling Synergistic Oxidation Processes for Efficient and Stable Blue Thermally Activated Delayed Fluorescence Devices , 2016, Advanced materials.

[5]  Young Hoon Son,et al.  Diphenanthroline Electron Transport Materials for the Efficient Charge Generation Unit in Tandem Organic Light-Emitting Diodes , 2017 .

[6]  K. Leo,et al.  Degradation Mechanisms and Reactions in Organic Light-Emitting Devices. , 2015, Chemical reviews.

[7]  C. Adachi,et al.  High efficiency pure blue thermally activated delayed fluorescence molecules having 10H-phenoxaborin and acridan units. , 2015, Chemical communications.

[8]  Young Hoon Son,et al.  High efficiency red top-emitting micro-cavity organic light emitting diodes. , 2014, Optics express.

[9]  Jang‐Joo Kim,et al.  High‐Efficiency Sky Blue to Ultradeep Blue Thermally Activated Delayed Fluorescent Diodes Based on Ortho‐Carbazole‐Appended Triarylboron Emitters: Above 32% External Quantum Efficiency in Blue Devices , 2018, Advanced Optical Materials.

[10]  G. Kim,et al.  An accurate measurement of the dipole orientation in various organic semiconductor films using photoluminescence exciton decay analysis. , 2019, Physical chemistry chemical physics : PCCP.

[11]  S. Nomura,et al.  One-Step Borylation of 1,3-Diaryloxybenzenes Towards Efficient Materials for Organic Light-Emitting Diodes. , 2015, Angewandte Chemie.

[12]  C. Adachi,et al.  A New Design Strategy for Efficient Thermally Activated Delayed Fluorescence Organic Emitters: From Twisted to Planar Structures , 2017, Advanced materials.

[13]  C. Adachi,et al.  Efficient blue organic light-emitting diodes employing thermally activated delayed fluorescence , 2014, Nature Photonics.

[14]  Yuanbin Kang,et al.  Lifetime enhancement of blue thermally activated delayed fluorescent devices by separated carrier channels using dibenzofuran-triazine type hosts , 2018, Journal of Industrial and Engineering Chemistry.

[15]  A. Wakamiya,et al.  Highly emissive organic solids containing 2,5-diboryl-1,4-phenylene unit. , 2006, Journal of the American Chemical Society.

[16]  Ken-Tsung Wong,et al.  Sky‐Blue Organic Light Emitting Diode with 37% External Quantum Efficiency Using Thermally Activated Delayed Fluorescence from Spiroacridine‐Triazine Hybrid , 2016, Advanced materials.

[17]  H. Kita,et al.  Dimesitylarylborane-based luminescent emitters exhibiting highly-efficient thermally activated delayed fluorescence for organic light-emitting diodes , 2016 .

[18]  Hironori Kaji,et al.  A light-emitting mechanism for organic light-emitting diodes: molecular design for inverted singlet–triplet structure and symmetry-controlled thermally activated delayed fluorescence , 2015 .

[19]  G. Hernández-Sosa,et al.  Sulfone-Based Deep Blue Thermally Activated Delayed Fluorescence Emitters: Solution-Processed Organic Light-Emitting Diodes with High Efficiency and Brightness , 2017 .

[20]  C. Adachi,et al.  Highly efficient blue electroluminescence based on thermally activated delayed fluorescence. , 2015, Nature materials.

[21]  H. Kita,et al.  Light blue and green thermally activated delayed fluorescence from 10H-phenoxaborin-derivatives and their application to organic light-emitting diodes , 2015 .

[22]  Tobias D. Schmidt,et al.  Efficiency Enhancement of Organic Light‐Emitting Diodes Incorporating a Highly Oriented Thermally Activated Delayed Fluorescence Emitter , 2014 .

[23]  Lian Duan,et al.  Sterically shielded blue thermally activated delayed fluorescence emitters with improved efficiency and stability , 2016 .

[24]  Alán Aspuru-Guzik,et al.  An Alternative Host Material for Long‐Lifespan Blue Organic Light‐Emitting Diodes Using Thermally Activated Delayed Fluorescence , 2017, Advanced science.

[25]  I. Osaka,et al.  On-top π-stacking of quasiplanar molecules in hole-transporting materials: inducing anisotropic carrier mobility in amorphous films. , 2014, Angewandte Chemie.

[26]  C. Adachi,et al.  Design of efficient thermally activated delayed fluorescence materials for pure blue organic light emitting diodes. , 2012, Journal of the American Chemical Society.

[27]  C. Adachi,et al.  Triarylboron-Based Fluorescent Organic Light-Emitting Diodes with External Quantum Efficiencies Exceeding 20 . , 2015, Angewandte Chemie.

[28]  Motoyuki Uejima,et al.  Highly Efficient Blue Electroluminescence Using Delayed-Fluorescence Emitters with Large Overlap Density between Luminescent and Ground States , 2015 .

[29]  C. Adachi,et al.  Controlling Singlet-Triplet Energy Splitting for Deep-Blue Thermally Activated Delayed Fluorescence Emitters. , 2017, Angewandte Chemie.

[30]  C. Adachi,et al.  Excited state engineering for efficient reverse intersystem crossing , 2018, Science Advances.

[31]  Shintaro Nomura,et al.  Ultrapure Blue Thermally Activated Delayed Fluorescence Molecules: Efficient HOMO–LUMO Separation by the Multiple Resonance Effect , 2016, Advanced materials.

[32]  D. Yokoyama Molecular orientation in small-molecule organic light-emitting diodes , 2011 .

[33]  Arvi Rauk,et al.  On the calculation of multiplet energies by the hartree-fock-slater method , 1977 .

[34]  Stefanie Griesbeck,et al.  Recent developments in and perspectives on three-coordinate boron materials: a bright future , 2016, Chemical science.

[35]  H. Kaji,et al.  π-Extended planarized triphenylboranes with thiophene spacers. , 2013, Organic letters.