journal article·2021-08

Administration of the D-A structure and steric hindrance effect to construct efficient red emitters for high-performance OLEDs with low efficiency roll-off

Guan-Yu Ding, Chun-Xiu Zang, Han Zhang, Zhong-Min Su, Guang-Fu Li, Li-Li Wen, Xu Han, Wen-Fa Xie, Guo-Gang Shan

Dyes and Pigments· Volume 192
Publisher page

Abstract

Abstract Restricted by the energy-gap law and π-π stacking, developing highly efficient red emitting materials and corresponding organic light-emitting diodes (OLEDs) having the emission over 600 nm is a formidable challenge. Three red emitters, namely DPABz-TPA, 2DPABz-TPA, and 3DPABz-TPA, are developed bearing mono-, bis-, and tri-[2,1,3]benzothiadiazole (Bz) substituted triphenylamine (TPA) as the emissive core and bulky diphenylamine (DPA) as the steric protection units. All compounds display strong red emission with peaks at 645 nm and high efficiency up to 38%. Compared with reference molecule DPABz-TPA, both 2DPABz-TPA and 3DPABz-TPA exhibit higher radiative transition rate and thermal stability. The OLEDs based on 2DPABz-TPA and 3DPABz-TPA thus show superior EL efficiencies of the maximum current efficiency of 2.5 and 2.4 cd A−1, and external quantum efficiency of 2.9% and 3.2% compared with those of DPABz-TPA (1.9 cd A−1 and 2.1%). More importantly, the efficiency roll-off of OLED based on sterically protected 3DPABz-TPA obviously decreases owing to limited intermolecular packing. These results indicate that the strategy combined multiple donor-acceptor units and steric hindrance effect is favorable for constructing robust red emitters for efficient OLEDs.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Organic Light-Emitting Diodes Research · Organic Electronics and Photovoltaics · Conducting polymers and applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (49)

Show source-provided references
1. Organic electroluminescent diodes10.1063/1.98799 ↗
2. Organic light emitting diodes: energy saving lighting technology—a review10.1016/j.rser.2012.02.021 ↗
3. Liquid crystal display and organic light-emitting diode display: present status and future perspectives10.1038/lsa.2017.168 ↗
4. Three-color, tunable, organic light-emitting devices10.1126/science.276.5321.2009 ↗
5. White organic light-emitting diodes with fluorescent tube efficiency10.1038/nature08003 ↗
6. Highly efficient organic light-emitting diodes from delayed fluorescence10.1038/nature11687 ↗
7. Efficient radical-based light-emitting diodes with doublet emission10.1038/s41586-018-0695-9 ↗
8. Yellow/orange emissive heavy-metal complexes as phosphors in monochromatic and white organic light-emitting devices10.1039/C4CS00110A ↗
9. Functionalization of phosphorescent emitters and their host materials by main-group elements for phosphorescent organic light-emitting devices10.1039/C5CS00424A ↗
10. Application of the energy gap law to the decay of charge-transfer excited states10.1021/ja00366a051 ↗
11. The energy gap law for triplet states in Pt-containing conjugated polymers and monomers10.1021/ja010986s ↗
12. Tuning the excited-state properties of platinum(II) diimine dithiolate complexes10.1021/ja951345y ↗
13. 1,4-Bis(diarylamino)-2,5-bis(4-cyanophenylethenyl)benzenes: fluorophores exhibiting efficient red and near-infrared emissions in solid state10.1002/anie.201108943 ↗
14. Rapid room temperature synthesis of red iridium(iii) complexes containing a four-membered Ir-S-C-S chelating ring for highly efficient OLEDs with EQE over 30%10.1039/C8SC05605F ↗
15. Triphenylamine-dendronized pure red iridium phosphors with superior OLED efficiency/color purity trade-offs10.1002/anie.200604094 ↗
16. Rational design and characterization of heteroleptic phosphorescent complexes for highly efficient deep-red organic light-emitting devices10.1021/acsami.7b00348 ↗
17. Highly efficient deep-red organic light-emitting devices based on asymmetric iridium(III) complexes with the thianthrene 5,5,10,10-tetraoxide moiety10.1021/acsami.9b06749 ↗
18. Improving the efficiency of red thermally activated delayed fluorescence organic light‐emitting diode by rational isomer engineering10.1002/adfm.202002681 ↗
19. Molecular design to regulate the photophysical properties of multifunctional TADF emitters towards high-performance TADF-based OLEDs with EQEs up to 22.4% and small efficiency roll-offs10.1039/C7SC04669C ↗
20. Realizing 22.5% external quantum efficiency for solution-processed thermally activated delayed-fluorescence OLEDs with red emission at 622 nm via a synergistic strategy of molecular engineering and host selection10.1002/adma.201901404 ↗
21. Red organic light-emitting diode with external quantum efficiency beyond 20% based on a novel thermally activated delayed fluorescence emitter10.1002/advs.201800436 ↗
22. Dibenzo[a,j]phenazine-cored donor–acceptor–donor compounds as green-to-red/NIR thermally activated delayed fluorescence organic light emitters10.1002/anie.201600113 ↗
23. Synthesis and characterization of efficient luminescent materials based on 2,1,3-benzothiadiazole with carbazole moieties10.1016/j.synthmet.2011.01.020 ↗
24. Towards highly efficient red thermally activated delayed fluorescence materials by the control of intra-molecularπ–πstacking interactions
25. In situ generation of red-emissive AIEgens from commercial sources for nondoped OLEDs10.1021/acsomega.8b02372 ↗
26. Twist angle and rotation freedom effects on luminescent donor-acceptor materials: crystal structures, photophysical properties, and OLED application10.1002/adom.201600608 ↗
27. Donor–Acceptor–Donor-based π-conjugated oligomers for nonlinear Optics and near-IR emission10.1021/cm201424a ↗
28. Doubly ortho-linked quinoxaline/diphenylfluorene hybrids as bipolar, fluorescent chameleons for optoelectronic applications10.1021/ja062660v ↗
29. Unconventional three-armed luminogens exhibiting both aggregation-induced emission and thermally activated delayed fluorescence resulting in high-performing solution-processed organic light-emitting diodes10.1021/acsami.7b19681 ↗
30. Self-host blue-emitting iridium dendrimer with carbazole dendrons: nondoped phosphorescent organic light-emitting diodes10.1002/anie.201307311 ↗
31. Twisted intramolecular charge transfer state for long-wavelength thermally activated delayed fluorescence10.1021/cm402428a ↗
32. Star-shaped thermally activated delayed fluorescence emitters with a tri-armed arylsulfonic acceptor for efficient solution processed organic light emitting diodes10.1039/C9TC07049D ↗
33. Highly efficient near-infrared organic light-emitting diode based on a butterfly-shaped donor–acceptor chromophore with strong solid-state fluorescence and a large proportion of radiative excitons10.1002/anie.201308486 ↗
34. Benzothiadiazole derivatives as fluorescence imaging probes: beyond classical scaffolds10.1021/ar500468p ↗
35. Teaching an old acceptor new tricks: rationally employing 2,1,3-benzothiadiazole as input to design a highly efficient red thermally activated delayed fluorescence emitter10.1039/C7TC00025A ↗
36. Facile access to deep red/near-infrared emissive AIEgens for efficient non-doped OLEDs10.1039/C8SC01377B ↗
37. Multi-triphenylamine-substituted bis(thiophenyl)benzothiadiazoles as highly efficient solution-processed non-doped red light-emitters for OLEDs10.1039/C4TC02618G ↗
38. Highly efficient solid-state near-infrared emitting material based on triphenylamine and diphenylfumaronitrile with an EQE of 2.58% in nondoped organic light-emitting diode10.1002/adfm.201503344 ↗
39. Frisch GWT · 2009
40. The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors10.1016/j.jphotochem.2020.112936 ↗
41. Palladium-catalyzed decarbonylative borylation of carboxylic acids: tuning reaction selectivity by computation10.1002/anie.201810145 ↗
42. Photo-irradiated E/Z isomerization reaction of star-shaped isomers containing two cyanostilbene arms with charge transfer excited states10.1039/C8CP05581E ↗
43. Diketopyrrolopyrrole-based donor–acceptor conjugated microporous polymers for visible-light-driven photocatalytic hydrogen production from water10.1021/acs.macromol.9b02488 ↗
44. High-efficiency organic electroluminescent materials based on the D–A–D type with sterically hindered methyl groups10.1039/D0TC00596G ↗
45. Efficient red fluorescent OLEDs based on aggregation-induced emission combined with hybridized local and charge transfer state
46. Employing ~100% excitons in OLEDs by utilizing a fluorescent molecule with hybridized local and charge-transfer excited state10.1002/adfm.201301750 ↗
47. Achieving high-performance solution-processed deep-red/near-infrared organic light-emitting diodes with a phenanthroline-based and wedge-shaped fluorophore10.1002/aelm.201800677 ↗
48. Rational design of aggregation-induced emission luminogen with weak electron donor-acceptor interaction to achieve highly efficient undoped bilayer OLEDs10.1021/am505036a ↗
49. Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications10.1002/adma.201004554 ↗