Thermally Activated Delayed Fluorescence from Azasiline Based Intramolecular Charge-Transfer Emitter (DTPDDA) and a Highly Efficient Blue Light Emitting Diode

For electroluminescence with delayed fluorescence, the azasiline unit has been introduced for the first time as a donor in a thermally activated delayed fluorescence (TADF) material. The TADF material (DTPDDA) shows strong intramolecular charge transfer (CT) character with large spatial separation with the acceptor of triazine leading to narrow splitting of singlet and triplet excited states for the efficient reverse intersystem crossing (RISC). A blue organic light emitting diode (OLED) based on DTPDDA not only displays deep blue in the Commission Internationale de L’Eclairage (CIE) coordinates of (0.149, 0.197) but also exhibits a high external quantum efficiency (EQE) of 22.3% which is the highest value ever reported for a blue fluorescent OLED. Theoretical prediction based on transient photoluminescence (PL) and optical simulation result agrees well with the achieved EQE indicating the successful conversion of triplet excitons to singlet in the blue fluorescent OLED by using DTPDDA.

[1]  H. Gilman,et al.  The Reaction of Some Silicon Hydrides with Sulfur-containing Heterocycles and Related Compounds1 , 1958 .

[2]  Kwon-Hyeon Kim,et al.  Phosphorescent dye-based supramolecules for high-efficiency organic light-emitting diodes , 2014, Nature Communications.

[3]  Haitao Sun,et al.  Reliable Prediction with Tuned Range-Separated Functionals of the Singlet-Triplet Gap in Organic Emitters for Thermally Activated Delayed Fluorescence. , 2015, Journal of chemical theory and computation.

[4]  Kwon-Hyeon Kim,et al.  Highly Efficient Organic Light‐Emitting Diodes with Phosphorescent Emitters Having High Quantum Yield and Horizontal Orientation of Transition Dipole Moments , 2014, Advanced materials.

[5]  Dong-Seok Leem,et al.  Effectiveness of p-dopants in an organic hole transporting material , 2009 .

[6]  S. Farid,et al.  Transition from Charge‐Transfer to Largely Locally Excited Exciplexes, from Structureless to Vibrationally Structured Emissions , 2015, Photochemistry and photobiology.

[7]  Kristiaan Neyts,et al.  Determining emissive dipole orientation in organic light emitting devices by decay time measurement , 2012 .

[8]  William J. Potscavage,et al.  Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence. , 2014, Journal of the American Chemical Society.

[9]  Dong-Seok Leem,et al.  Low driving voltage and high stability organic light-emitting diodes with rhenium oxide-doped hole transporting layer , 2007 .

[10]  J. Ohshita Conjugated Oligomers and Polymers Containing Dithienosilole Units , 2009 .

[11]  Jun Yeob Lee,et al.  Above 30% External Quantum Efficiency in Blue Phosphorescent Organic Light‐Emitting Diodes Using Pyrido[2,3‐b]indole Derivatives as Host Materials , 2013, Advanced materials.

[12]  Yun‐Hi Kim,et al.  High‐Purity‐Blue and High‐Efficiency Electroluminescent Devices Based on Anthracene , 2005 .

[13]  Chih-I Wu,et al.  A high performance inverted organic light emitting diode using an electron transporting material with low energy barrier for electron injection , 2011 .

[14]  Kazunari Yoshizawa,et al.  Computational Prediction for Singlet- and Triplet-Transition Energies of Charge-Transfer Compounds. , 2013, Journal of chemical theory and computation.

[15]  Mei-Hsin Chen,et al.  Rubidium-Carbonate-Doped 4,7-Diphenyl-1,10-phenanthroline Electron Transporting Layer for High-Efficiency p-i-n Organic Light Emitting Diodes , 2009 .

[16]  Jang‐Joo Kim,et al.  Efficient triplet harvesting by fluorescent molecules through exciplexes for high efficiency organic light-emitting diodes , 2013 .

[17]  Bo Seong Kim,et al.  Engineering of Mixed Host for High External Quantum Efficiency above 25% in Green Thermally Activated Delayed Fluorescence Device , 2014 .

[18]  Stephen R. Forrest,et al.  Transient analysis of organic electrophosphorescence. II. Transient analysis of triplet-triplet annihilation , 2000 .

[19]  Kwon-Hyeon Kim,et al.  Langevin and Trap‐Assisted Recombination in Phosphorescent Organic Light Emitting Diodes , 2014 .

[20]  S. Buchwald,et al.  A multiligand based Pd catalyst for C-N cross-coupling reactions. , 2010, Journal of the American Chemical Society.

[21]  Kwon-Hyeon Kim,et al.  Blue Phosphorescent Organic Light‐Emitting Diodes Using an Exciplex Forming Co‐host with the External Quantum Efficiency of Theoretical Limit , 2014, Advanced materials.

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

[23]  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.

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

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

[26]  Caroline Murawski,et al.  Comparing the emissive dipole orientation of two similar phosphorescent green emitter molecules in highly efficient organic light-emitting diodes , 2012 .

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

[28]  Xumu Zhang,et al.  Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chlorides. , 2006, The Journal of organic chemistry.

[29]  Christian Mayr,et al.  Organic Light‐Emitting Diodes with 30% External Quantum Efficiency Based on a Horizontally Oriented Emitter , 2013 .

[30]  K. Tamao,et al.  Silole-containing σ- and π-conjugated compounds , 1998 .

[31]  Kwon-Hyeon Kim,et al.  Exciplex‐Forming Co‐host for Organic Light‐Emitting Diodes with Ultimate Efficiency , 2013 .

[32]  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.

[33]  Yu-Hung Chen,et al.  Electronic and chemical properties of cathode structures using 4,7-diphenyl-1,10-phenanthroline doped with rubidium carbonate as electron injection layers , 2009 .

[34]  Chihaya Adachi,et al.  Efficient green thermally activated delayed fluorescence (TADF) from a phenoxazine-triphenyltriazine (PXZ-TRZ) derivative. , 2012, Chemical communications.

[35]  Caroline Murawski,et al.  Efficiency Roll‐Off in Organic Light‐Emitting Diodes , 2013, Advanced materials.

[36]  Dong-Seok Leem,et al.  Effect of host organic semiconductors on electrical doping , 2010 .

[37]  Sei‐Yong Kim,et al.  Thickness dependence of PL efficiency of organic thin films , 2009 .

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

[39]  Kwon-Hyeon Kim,et al.  A Fluorescent Organic Light‐Emitting Diode with 30% External Quantum Efficiency , 2014, Advanced materials.

[40]  J. Kido,et al.  High‐Performance Blue Phosphorescent OLEDs Using Energy Transfer from Exciplex , 2014, Advanced materials.

[41]  Wolfgang Brütting,et al.  Determination of molecular dipole orientation in doped fluorescent organic thin films by photoluminescence measurements , 2010 .