journal article·2020-10

Asymmetrically 2,7-difunctionalized carbazole-based donor-acceptor hybrids for deep blue electroluminescence applications

Vellaichamy Joseph, K.R. Justin Thomas, Snehasis Sahoo, Meenu Singh, Jwo-Huei Jou

Optical Materials· Volume 108
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Abstract

Abstract Asymmetrically 2,7-difunctionalized carbazoles decorated with cyano group and different conjugated chromophores have been synthesized by following Suzuki coupling reactions. Direct C–C coupling between cyanocarbazole and peripheral chromophores lead to twist structure of the molecules. As a result, it restricts the electronic communication between the chromophores and thereby confines absorption and emission maxima in shorter wavelength region. The positive solvatochromic emission spectrum of carbazole and triphenylamine substituted compounds is ascribed to synergistic effect of large structural reorganization and intramolecular charge transfer at excited state. Density functional theory (DFT) studies reveal the involvement of ICT from donor carbazole/triphenylamine to cyanocarbazole acceptor. OLED device containing a pyrene substituted dye (5 wt% in CBP host) displayed deep blue electroluminescence with the EQE of 3.0% and CIE of (0.16, 0.06). The superior device performance can be attributed to favorable energy level alignment of this dye with CBP host and complete energy transfer from the host to guest.
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Research context

OpenAlex topics: Organic Light-Emitting Diodes Research · Luminescence and Fluorescent Materials · Organic Electronics and Photovoltaics

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

References (37)

Show source-provided references
1. Organic electroluminescent diodes10.1063/1.98799 ↗
2. Recent advances of the emitters for high performance deep-blue organic light-emitting diodes10.1039/C4TC02474E ↗
3. Efficient tuning of electroluminescence from sky-blue to deep-blue by changing the constitution of spirobenzofluorene derivatives10.1016/j.dyepig.2014.04.019 ↗
4. Rational design of push-pull fluorene dyes: synthesis and structure-photophysics relationship10.1002/chem.201600581 ↗
5. Conformationally restricted bicarbazoles with phenylene bridges displaying deep-blue emission and high triplet energies: systematic structure-property relationships10.1039/C8CP01636D ↗
6. Bromine substituted triphenylamine derivatives with improved hole-mobility for highly efficient green phosphorescent OLEDs with a low operating voltage10.1039/C6TC03020C ↗
7. Synthesis, characterization and photophysical study of ethynyl pyrene derivatives as promising materials for organic optoelectronics10.1016/j.jlumin.2014.12.036 ↗
8. Efficient nondoped blue fluorescent organic light-emitting diodes (OLEDs) with a high external quantum efficiency of 9.4% @1000 cd/m2 based on phenanthroimidazole-anthracene derivative10.1002/adfm.201705813 ↗
9. Highly efficient emitters of ultra-deep-blue light made from chrysene chromophores10.1039/C5TC03749B ↗
10. Diphenylamino-substituted bicarbazole derivative: hole transporting material with high glass transition temperature, good electron and triplet excitons blocking capabilities and efficient hole injection10.1016/j.cplett.2016.12.027 ↗
11. Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes10.1016/j.dyepig.2016.09.062 ↗
12. Solution processable naphthalene and phenyl substituted carbazole core based hole transporting materials for efficient organic light-emitting diodes10.1039/C7TC03049E ↗
13. High-triplet-energy carbazole and fluorene tetrads10.1016/j.jlumin.2015.08.019 ↗
14. Bis-anthracene based donor-acceptor-type light-emitting dopants: highly efficient deep-blue emission in organic light-emitting devices10.1002/adfm.201302907 ↗
15. Highly efficient organic light-emitting diodes from delayed fluorescence10.1038/nature11687 ↗
16. 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 ↗
17. Highly efficient deep-blue electroluminescence from a charge-transfer emitter with stable donor skeleton10.1021/acsami.6b14638 ↗
18. Asymmetric triaryldiamines as thermally stable hole transporting layers for organic light-emitting devices10.1021/cm980186p ↗
19. Manipulating donor-acceptor interactions in carbazole-based emitters by chromophore choice to achieve near-UV emission10.1002/ejoc.201701285 ↗
20. Palladium-catalyzed cross-coupling reactions of organoboron compounds10.1021/cr00039a007 ↗
21. Bicarbazoles: systematic structure-property investigations on a series of conjugated carbazole dimers10.1021/jo3016538 ↗
22. Synthesis of asymmetric biphenyl derivatives for optoelectronic applications10.1016/j.optmat.2013.05.027 ↗
23. Pyrene-functionalized fluorene and carbazole derivatives as blue light emitters10.1021/jp300161k ↗
24. BODIPY-bridged push-pull chromophores for nonlinear optical applications10.1002/cphc.201402123 ↗
25. Synthesis and spectroscopic study of phenylenee(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems10.1016/j.tet.2010.05.016 ↗
26. Dipolemoment und elektronenstruktur von angeregten molekülen10.1515/zna-1955-0707 ↗
27. The solvent effect on fluorescence spectrum. Change of solvent-solute interaction during the life time of excited solution molecule10.1246/bcsj.28.690 ↗
28. Aggregation effects on the emission spectra and dynamics of model oligomers of MEH-PPV10.1021/jp904308h ↗
29. Carbazole electrochemistry: a short review10.1007/s10008-015-2973-x ↗
30. Cyanocarbazole derivatives for high-performance electroluminescent devices10.1002/adfm.200305144 ↗
31. Carbazole oligomers revisited: new additions at the 1- and 8-positions10.1039/c2ra21657d ↗
32. Simple carbazole based deep-blue emitters: the effect of spacer, linkage and end-capping cyano group on the photophysical and electroluminescent properties10.1016/j.dyepig.2017.12.061 ↗
33. Mind the gap10.1039/C3MH00098B ↗
34. Density functional thermochemistry (III). The role of exact exchange10.1063/1.464913 ↗
35. Development of the Colle-Salvette correlation-energy formula into a functional of the electron density10.1103/PhysRevB.37.785 ↗
36. Solvent effects on the optical spectra and excited state decay of triphenylamine-thiadiazole with hybridized local excitation and intramolecular charge transfer10.1021/jp5099409 ↗
37. Synthesis, characterization, physical properties and OLED application of single BN-fused perylene diimide10.1021/jo502296z ↗