High-performance red electrophosphorescent devices based on all-solution-processed hydrogen-bonded supramolecular material

An oligoamide strand bearing a guest phosphorescent unit, named 4HB-Irpiq, was designed and synthesized. The guest hydrogen-bonded strand 4HB-Irpiq could self-assemble via hydrogen-bonding interactions with the host hydrogen-bonded strand 4HB-CzNI into a hydrogen-bonded supramolecule, named 4HB-Irpiq-CzNI. In comparison with physical blends of the guest counterpart Irpiq with host small molecule CzNI, 4HB-Irpiq-CzNI shows a more efficient energy transfer process between host and guest in both dilute solution and doped film state, which could be attributed to the shortened spatial distance between the host and guest units. Moreover, compared with Irpiq, 4HB-Irpiq-CzNI shows a higher photoluminescence quantum yield in the neat-film state, indicating that 4HB-Irpiq-CzNI could be better at alleviating concentration quenching. As a consequence, a phosphorescent organic light-emitting diode with 4HB-Irpiq-CzNI and Irpiq as the light-emitting dopant has been fabricated based on all-solution-processing. The results indicate that OLEDs with 4HB-Irpiq-CzNI show dramatically improved performance over the counterpart Irpiq: with a lower turn-on voltage (6.0 vs. 7.6 V), higher maximum luminance (6446 vs. 2543 cd m−2) and current efficiency (7.0 vs. 4.3 cd A−1) as well as a lower efficiency roll-off. The hydrogen-bonded supramolecular 4HB-Irpiq-CzNI material shows one of the best performances among all-solution-processed red PhOLEDs.

[1]  Y. Huang,et al.  A novel H-bonding self-assembly heteromeric molecular duplex bearing host and guest energy transfer units as high-performance electroluminescent material , 2018 .

[2]  Wenjun Yang,et al.  A pair of conjoined donor–acceptor butterflies as promising solution-processable aggregation-enhanced emission FR/NIR EL emitters , 2017 .

[3]  Qiang Zhao,et al.  Phosphorescent Ionic Iridium(III) Complexes Displaying Counterion‐Dependent Emission Colors for Flexible Electrochromic Luminescence Device , 2017 .

[4]  Qiang Zhao,et al.  Circularly Polarized Phosphorescent Electroluminescence from Chiral Cationic Iridium(III) Isocyanide Complexes , 2017 .

[5]  Wei Huang,et al.  Solution-processed diarylfluorene derivatives for violet-blue amplified spontaneous emission and electroluminescence , 2017 .

[6]  Xin Yang,et al.  Solution-processed small-molecular white organic light-emitting diodes based on a thermally activated delayed fluorescence dendrimer , 2017 .

[7]  Sung‐Ho Jin,et al.  Solution-processable highly efficient deep-red and orange organic light-emitting diodes based on multi-functional Ir(III) complexes , 2017 .

[8]  Qiang Zhao,et al.  Highly efficient blue phosphorescent iridium(III) complexes with various ancillary ligands for partially solution-processed organic light-emitting diodes , 2017 .

[9]  Shi-jian Su,et al.  Efficient near-infrared emitting tetradentate bis-cyclometalated platinum (IV) complexes for solution-processed polymer light-emitting diodes , 2017 .

[10]  Weihua Chen,et al.  Poly(9,9-dioctylfluorene) based hyperbranched copolymers with three balanced emission colors for solution-processable hybrid white polymer light-emitting devices , 2017 .

[11]  Junbiao Peng,et al.  High Tg small-molecule phenanthroline derivatives as a potential universal hole-blocking layer for high power-efficiency and stable organic light-emitting diodes , 2017 .

[12]  Z. Cui,et al.  0.7% Roll-off for Solution-Processed Blue Phosphorescent OLEDs with a Novel Electron Transport Material , 2017 .

[13]  Li Wang,et al.  Exploring the influence of different ancillary ligands of heteroleptic Ir(III) complexes on the phosphorescent properties: Emissive rule and photodeactivation dynamics , 2017 .

[14]  X. Jing,et al.  Single molecular tuning of the charge balance in blue-emitting iridium dendrimers for efficient nondoped solution-processed phosphorescent OLEDs. , 2016, Chemical communications.

[15]  K. Y. Zhang,et al.  Utilization of Electrochromically Luminescent Transition‐Metal Complexes for Erasable Information Recording and Temperature‐Related Information Protection , 2016, Advanced materials.

[16]  K. Y. Zhang,et al.  Luminescent ion pairs with tunable emission colors for light-emitting devices and electrochromic switches† †Electronic supplementary information (ESI) available: Details of NMR and MS spectra. See DOI: 10.1039/c6sc02837c Click here for additional data file. , 2016, Chemical science.

[17]  R. Lu,et al.  Recent progress in the mechanochromism of phosphorescent organic molecules and metal complexes , 2016 .

[18]  W. Wong,et al.  Power-efficient solution-processed red organic light-emitting diodes based on an exciplex host and a novel phosphorescent iridium complex , 2016 .

[19]  Wenyong Lai,et al.  Distinct phosphorescence enhancement of red-emitting iridium(III) complexes with formyl-functionalized phenylpyridine ligands , 2016 .

[20]  Y. Qiu,et al.  New Insights into Tunable Volatility of Ionic Materials through Counter‐Ion Control , 2016 .

[21]  Wai-Yeung Wong,et al.  Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices. , 2015, Chemical Society reviews.

[22]  F. D’Souza,et al.  Modulation of Energy Transfer into Sequential Electron Transfer upon Axial Coordination of Tetrathiafulvalene in an Aluminum(III) Porphyrin-Free-Base Porphyrin Dyad. , 2015, Inorganic chemistry.

[23]  Ji-hoon Kim,et al.  Progress and perspective of iridium-containing phosphorescent polymers for light-emitting diodes , 2015 .

[24]  F. D’Souza,et al.  Multistep energy and electron transfer in a "V-configured" supramolecular BODIPY-azaBODIPY-fullerene triad: mimicry of photosynthetic antenna reaction-center events. , 2015, Chemistry.

[25]  S. Horng,et al.  Interface and thickness tuning for blade coated small-molecule organic light-emitting diodes with high power efficiency , 2013 .

[26]  Amitava Das,et al.  First demonstration of two-step FRET in a synthetic supramolecular assembly , 2013 .

[27]  Burkhard König,et al.  Chemical Degradation in Organic Light‐Emitting Devices: Mechanisms and Implications for the Design of New Materials , 2013, Advanced materials.

[28]  Jingbo Lan,et al.  Facile access to extremely efficient energy-transfer pairs via an unexpected reaction of squaraines with ketones. , 2012, Journal of the American Chemical Society.

[29]  Y. Y. Li,et al.  Synthesis and luminescent properties of blue sextuple-hydrogen-bond self-assembly molecular duplexes bearing 4-phenoxy-1,8-naphthalimide moieties , 2012 .

[30]  S. Perrier,et al.  Hyperbranched polymers by thiol-yne chemistry: from small molecules to functional polymers. , 2009, Journal of the American Chemical Society.

[31]  Junbiao Peng,et al.  A sextuple hydrogen bonding molecular duplex bearing 1,8-naphthalimide moieties and polymer light-emitting diode based on it , 2009 .

[32]  Chung-Wen Wu,et al.  H-Bonded Effects on Novel Supramolecular Dendrimers Containing Electron-Transporting Donor Dendrons and Single/Double H-Bonded Acceptor Emitters , 2006 .

[33]  J. S. Ferguson,et al.  Sequence-specific association in aqueous media by integrating hydrogen bonding and dynamic covalent interactions. , 2006, Journal of the American Chemical Society.

[34]  Yong Cao,et al.  New iridium complex as high-efficiency red phosphorescent emitter in polymer light-emitting devices , 2006 .

[35]  Richard D Smith,et al.  An extremely stable, self-complementary hydrogen-bonded duplex. , 2003, Chemical communications.

[36]  E. W. Meijer,et al.  Stability and Lifetime of Quadruply Hydrogen Bonded 2-Ureido-4[1H]-pyrimidinone Dimers , 2000 .

[37]  B. Gong,et al.  A Highly Stable, Six-Hydrogen-Bonded Molecular Duplex , 2000 .

[38]  B. Gong,et al.  A NEW APPROACH FOR THE DESIGN OF SUPRAMOLECULAR RECOGNITION UNITS : HYDROGEN-BONDED MOLECULAR DUPLEXES , 1999 .

[39]  J. Hedrick,et al.  Dendrimer-like Star Polymers , 1998 .

[40]  Zhaoxin Wu,et al.  Novel red phosphorescent polymers bearing both ambipolar and functionalized Ir(III) phosphorescent moieties for highly efficient organic light-emitting diodes. , 2015, Macromolecular rapid communications.

[41]  Jie Zhou,et al.  An efficient guest/host fluorescent energy transfer pair based on the naphthalimide skeleton, and its application in heavily-doped red organic light-emitting diodes , 2014 .