Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

The design of highly emissive and stable blue emitters for organic light emitting diodes (OLEDs) is still a challenge, justifying the intense research activity of the scientific community in this field. Recently, a great deal of interest has been devoted to the elaboration of emitters exhibiting a thermally activated delayed fluorescence (TADF). By a specific molecular design consisting into a minimal overlap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) due to a spatial separation of the electron-donating and the electron-releasing parts, luminescent materials exhibiting small S1–T1 energy splitting could be obtained, enabling to thermally upconvert the electrons from the triplet to the singlet excited states by reverse intersystem crossing (RISC). By harvesting both singlet and triplet excitons for light emission, OLEDs competing and sometimes overcoming the performance of phosphorescence-based OLEDs could be fabricated, justifying the interest for this new family of materials massively popularized by Chihaya Adachi since 2012. In this review, we proposed to focus on the recent advances in the molecular design of blue TADF emitters for OLEDs during the last few years.

[1]  Chuncheng Chen,et al.  Mechanism of TiO2-assisted photocatalytic degradation of dyes under visible irradiation: photoelectrocatalytic study by TiO2-film electrodes. , 2005, The journal of physical chemistry. B.

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

[3]  F. Dumur Zinc complexes in OLEDs: An overview , 2014 .

[4]  Chihaya Adachi,et al.  Oxadiazole- and triazole-based highly-efficient thermally activated delayed fluorescence emitters for organic light-emitting diodes , 2013 .

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

[6]  Chien-Hong Cheng,et al.  A Highly Efficient Universal Bipolar Host for Blue, Green, and Red Phosphorescent OLEDs , 2010, Advanced materials.

[7]  P. Chou,et al.  Feeling blue? Blue phosphors for OLEDs , 2011 .

[8]  Qisheng Zhang,et al.  High-efficiency deep-blue organic light-emitting diodes based on a thermally activated delayed fluorescence emitter , 2014 .

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

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

[11]  In Seob Park,et al.  High-performance blue organic light-emitting diodes with 20% external electroluminescence quantum efficiency based on pyrimidine-containing thermally activated delayed fluorescence emitters , 2016 .

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

[13]  Hao-Wu Lin,et al.  Thermally activated delayed fluorescence emitters with a m,m-di-tert-butyl-carbazolyl benzoylpyridine core achieving extremely high blue electroluminescence efficiencies , 2017 .

[14]  C. Tang,et al.  Organic Electroluminescent Diodes , 1987 .

[15]  Chien‐Hong Cheng,et al.  A high triplet energy, high thermal stability oxadiazole derivative as the electron transporter for highly efficient red, green and blue phosphorescent OLEDs , 2015 .

[16]  C. Adachi,et al.  Highly efficient organic light-emitting diodes by delayed fluorescence , 2013 .

[17]  Yao Liu,et al.  Thermally cross-linkable thermally activated delayed fluorescent materials for efficient blue solution-processed organic light-emitting diodes , 2016 .

[18]  Yuan-Cheng Cao,et al.  Recent advancements of high efficient donor–acceptor type blue small molecule applied for OLEDs , 2017 .

[19]  Understanding the Fluorescence of TADF Light-Emitting Dyes. , 2016, The journal of physical chemistry. A.

[20]  Chun‐Sing Lee,et al.  Blue-emitting organic electrofluorescence materials: progress and prospective , 2015 .

[21]  Seok-Ho Hwang,et al.  Carbazole-carboline core as a backbone structure of high triplet energy host materials , 2015 .

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

[23]  Zongliang Xie,et al.  Recent advances in organic thermally activated delayed fluorescence materials. , 2017, Chemical Society reviews.

[24]  Xiu-li Wang,et al.  Phosphorus-containing copolyesters: The effect of ionic group and its analogous phosphorus heterocycles on their flame-retardant and anti-dripping performances , 2015 .

[25]  Yuping Dong,et al.  Novel Carbazol-Pyridine-Carbonitrile Derivative as Excellent Blue Thermally Activated Delayed Fluorescence Emitter for Highly Efficient Organic Light-Emitting Devices. , 2015, ACS applied materials & interfaces.

[26]  L. Liao,et al.  Bipolar host materials for high efficiency phosphorescent organic light emitting diodes: tuning the HOMO/LUMO levels without reducing the triplet energy in a linear system , 2013 .

[27]  M. Cho,et al.  Thermally activated delayed fluorescence blue dopants and hosts: from the design strategy to organic light-emitting diode applications , 2016 .

[28]  X. Jing,et al.  Blue Thermally Activated Delayed Fluorescence Polymers with Nonconjugated Backbone and Through-Space Charge Transfer Effect. , 2017, Journal of the American Chemical Society.

[29]  Zhongbin Wu,et al.  High‐Performance Hybrid White Organic Light‐Emitting Diodes with Superior Efficiency/Color Rendering Index/Color Stability and Low Efficiency Roll‐Off Based on a Blue Thermally Activated Delayed Fluorescent Emitter , 2016 .

[30]  B. H. Koh,et al.  Synthesis and characterization of diphenylamine derivative containing malononitrile for thermally activated delayed fluorescent emitter , 2017 .

[31]  Chunmiao Han,et al.  Multi-dipolar Chromophores Featuring Phosphine Oxide as Joint Acceptor: A New Strategy toward High-Efficiency Blue Thermally Activated Delayed Fluorescence Dyes , 2016 .

[32]  Pengfei Wang,et al.  Synthesis of Multiaryl‐Substituted Pyridine Derivatives and Applications in Non‐doped Deep‐Blue OLEDs as Electron‐Transporting Layer with High Hole‐Blocking Ability , 2010, Advanced materials.

[33]  Soon-Ki Kwon,et al.  Azasiline-based thermally activated delayed fluorescence emitters for blue organic light emitting diodes , 2017 .

[34]  T. Ozturk,et al.  Triarylborane-Based Materials for OLED Applications , 2017, Molecules.

[35]  Jang‐Joo Kim,et al.  Crystal Organic Light‐Emitting Diodes with Perfectly Oriented Non‐Doped Pt‐Based Emitting Layer , 2016, Advanced materials.

[36]  Junji Kido,et al.  3,3′‐Bicarbazole‐Based Host Materials for High‐Efficiency Blue Phosphorescent OLEDs with Extremely Low Driving Voltage , 2012, Advanced materials.

[37]  Chihaya Adachi,et al.  High‐Efficiency Blue Organic Light‐Emitting Diodes Based on Thermally Activated Delayed Fluorescence from Phenoxaphosphine and Phenoxathiin Derivatives , 2016, Advanced materials.

[38]  C. R. Mayer,et al.  Random Copolymers with Pendant Cationic Mixed‐Ligand Terpyridine‐Based Iridium (III) Complexes: Synthesis and Application in Light‐Emitting Devices , 2011 .

[39]  A. Weller,et al.  Solvent influence on the magnetic field effect of polymethylene-linked photogenerated radical ion pairs , 1989 .

[40]  S. Yoo,et al.  Rigidity-Induced Delayed Fluorescence by Ortho Donor-Appended Triarylboron Compounds: Record-High Efficiency in Pure Blue Fluorescent Organic Light-Emitting Diodes. , 2017, ACS applied materials & interfaces.

[41]  A. Monkman,et al.  Regio- and conformational isomerization critical to design of efficient thermally-activated delayed fluorescence emitters , 2017, Nature Communications.

[42]  Tetsuo Tsutsui,et al.  Organic electroluminescent device having a hole conductor as an emitting layer , 1989 .

[43]  Effect of increasing electron donor units for high-efficiency blue thermally activated delayed fluorescence , 2017 .

[44]  Ken-Tsung Wong,et al.  Efficient and Tunable Thermally Activated Delayed Fluorescence Emitters Having Orientation‐Adjustable CN‐Substituted Pyridine and Pyrimidine Acceptor Units , 2016 .

[45]  D. Gaspar,et al.  OLED fundamentals : materials, devices, and processing of organic light-emitting diodes , 2015 .

[46]  M. Gong,et al.  Design of ortho-linkage carbazole-triazine structure for high-efficiency blue thermally activated delayed fluorescent emitters , 2016 .

[47]  N. Turro,et al.  Principles of Molecular Photochemistry: An Introduction , 2008 .

[48]  Yun Chi,et al.  Functional Pyrimidine-Based Thermally Activated Delay Fluorescence Emitters: Photophysics, Mechanochromism, and Fabrication of Organic Light-Emitting Diodes. , 2017, Chemistry.

[49]  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.

[50]  Hao-Wu Lin,et al.  A Method for Reducing the Singlet-Triplet Energy Gaps of TADF Materials for Improving the Blue OLED Efficiency. , 2016, ACS applied materials & interfaces.

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

[52]  J. Kido,et al.  1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices , 1993 .

[53]  M. Berberan-Santos,et al.  Unusually Strong Delayed Fluorescence of C70 , 1996 .

[54]  Ken-Tsung Wong,et al.  Enhanced electroluminescence based on thermally activated delayed fluorescence from a carbazole-triazine derivative. , 2013, Physical chemistry chemical physics : PCCP.

[55]  C. Adachi,et al.  Thermally Activated Delayed Fluorescence from Pentacarbazorylbenzonitrile , 2016 .

[56]  D. Gigmes,et al.  Iridium (III) complexes as promising emitters for solid–state Light–Emitting Electrochemical Cells (LECs) , 2012 .

[57]  H. Kita,et al.  A Novel Family of Boron‐Containing Hole‐Blocking Amorphous Molecular Materials for Blue‐ and Blue–Violet‐Emitting Organic Electroluminescent Devices , 2002 .

[58]  Andrew P. Monkman,et al.  The Importance of Vibronic Coupling for Efficient Reverse Intersystem Crossing in Thermally Activated Delayed Fluorescence Molecules , 2016, Chemphyschem : a European journal of chemical physics and physical chemistry.

[59]  Jean-Luc Brédas,et al.  Up-Conversion Intersystem Crossing Rates in Organic Emitters for Thermally Activated Delayed Fluorescence: Impact of the Nature of Singlet vs Triplet Excited States. , 2017, Journal of the American Chemical Society.

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

[61]  Arunandan Kumar,et al.  Phosphine oxide functionalized pyrenes as efficient blue light emitting multifunctional materials for organic light emitting diodes , 2015 .

[62]  J. Kido,et al.  High Power Efficiency Blue-to-Green Organic Light-Emitting Diodes Using Isonicotinonitrile-Based Fluorescent Emitters. , 2017, Chemistry, an Asian journal.

[63]  Chuluo Yang,et al.  Blue fluorescent emitters: design tactics and applications in organic light-emitting diodes. , 2013, Chemical Society reviews.

[64]  Soon-Ki Kwon,et al.  Thermally Activated Delayed Fluorescence from Azasiline Based Intramolecular Charge-Transfer Emitter (DTPDDA) and a Highly Efficient Blue Light Emitting Diode , 2015 .

[65]  E. Zysman‐Colman,et al.  Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light‐Emitting Diodes , 2017, Advanced materials.

[66]  A. Monkman,et al.  An optical and electrical study of full thermally activated delayed fluorescent white organic light-emitting diodes , 2017, Scientific Reports.

[67]  Pei-Yun Huang,et al.  New Molecular Design Concurrently Providing Superior Pure Blue, Thermally Activated Delayed Fluorescence and Optical Out-Coupling Efficiencies. , 2017, Journal of the American Chemical Society.

[68]  Abhishek P. Kulkarni,et al.  Electron Transport Materials for Organic Light-Emitting Diodes , 2004 .

[69]  S. Forrest,et al.  Highly efficient phosphorescent emission from organic electroluminescent devices , 1998, Nature.

[70]  W. Brütting,et al.  High-efficiency fluorescent organic light-emitting diodes enabled by triplet-triplet annihilation and horizontal emitter orientation , 2014 .

[71]  Hideo Taka,et al.  Luminescent alternating boron quinolate–fluorene copolymers exhibiting high electron mobility , 2010 .

[72]  Jang Hyuk Kwon,et al.  Controlling the exciton lifetime of blue thermally activated delayed fluorescence emitters using a heteroatom-containing pyridoindole donor moiety , 2017 .

[73]  J. Gražulevičius,et al.  Carbazole- and phenylindole-based new host materials for phosphorescent organic light emitting diodes , 2013 .

[74]  J. Kido,et al.  Significant Enhancement of Blue OLED Performances through Molecular Engineering of Pyrimidine‐Based Emitter , 2017 .

[75]  Jingui Qin,et al.  Organic host materials for phosphorescent organic light-emitting diodes. , 2011, Chemical Society reviews.

[76]  Shi-jian Su,et al.  Design Strategy of Blue and Yellow Thermally Activated Delayed Fluorescence Emitters and Their All‐Fluorescence White OLEDs with External Quantum Efficiency beyond 20% , 2016 .

[77]  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 .

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

[79]  F. Dumur Recent advances in organic light-emitting devices comprising copper complexes: A realistic approach for low-cost and highly emissive devices? , 2015 .

[80]  T. Nabeshima,et al.  Phosphorus-containing chiral molecule for fullerene recognition based on concave/convex interaction. , 2014, Journal of the American Chemical Society.

[81]  Hao‐Wu Lin,et al.  A thermally activated delayed blue fluorescent emitter with reversible externally tunable emission , 2016 .

[82]  T. Nabeshima,et al.  Tuning the depth of bowl-shaped phosphine hosts: capsule and pseudo-cage architectures in host-guest complexes with C60 fullerene. , 2015, Chemical communications.

[83]  T. Hasegawa,et al.  Synthesis of Phosphorus-Centered and Chalcogen-Bridged Concave Molecules: Modulation of Bowl Geometries and Packing Structures by Changing Bridging Atoms. , 2016, Organic letters.

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

[85]  Stephan Winter,et al.  Photoluminescence degradation of blue OLED emitters , 2008, SPIE Photonics Europe.

[86]  Blue Thermally Activated Delayed Fluorescence Molecule Having Acridane and Cyanobenzene Units , 2016 .

[87]  M. Gather,et al.  Get it white: color-tunable AC/DC OLEDs , 2015, Light: Science & Applications.

[88]  A. Monkman,et al.  Using Guest-Host Interactions To Optimize the Efficiency of TADF OLEDs. , 2016, The journal of physical chemistry letters.

[89]  Stephen R. Forrest,et al.  EXCITONIC SINGLET-TRIPLET RATIO IN A SEMICONDUCTING ORGANIC THIN FILM , 1999 .

[90]  F. Dumur,et al.  Triphenylamines and 1,3,4-oxadiazoles: a versatile combination for controlling the charge balance in organic electronics , 2014 .

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

[92]  Atsushi Kawada,et al.  Efficient up-conversion of triplet excitons into a singlet state and its application for organic light emitting diodes , 2011 .

[93]  Ji Han Kim,et al.  Recent Progress in High‐Efficiency Blue‐Light‐Emitting Materials for Organic Light‐Emitting Diodes , 2017 .

[94]  James I. Fells,et al.  Discovery of fused tricyclic core containing HCV NS5A inhibitors with pan-genotype activity. , 2016, Bioorganic & medicinal chemistry letters.

[95]  Pei-Yun Huang,et al.  A New Molecular Design Based on Thermally Activated Delayed Fluorescence for Highly Efficient Organic Light Emitting Diodes. , 2016, Journal of the American Chemical Society.

[96]  Chun-Sing Lee,et al.  Bipolar cyano-substituted pyridine derivatives for applications in organic light-emitting devices , 2012 .

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

[98]  Seok-Ho Hwang,et al.  Stable Blue Thermally Activated Delayed Fluorescent Organic Light‐Emitting Diodes with Three Times Longer Lifetime than Phosphorescent Organic Light‐Emitting Diodes , 2015, Advanced materials.

[99]  Qisheng Zhang,et al.  Nearly 100% Internal Quantum Efficiency in Undoped Electroluminescent Devices Employing Pure Organic Emitters , 2015, Advanced materials.