Abstract
The fluorescent molecule N,N-bis(3',5'–bis(trifluoromethyl)-[1,1'–biphenyl]-4–yl)perylen-3-amine (TFPA) was designed and synthesized by introducing the strong electron-withdrawing trifluoromethyl group and the strong electron-donating diphenylamino group, with perylene as the core. The structure of the target product was identified by nuclear magnetic resonance, and its UV–vis absorption properties, fluorescence emission properties, quantum yield and lifetime were studied systematically. The results showed that the HOMO of TFPA was mainly localized in the perylene part with a small part localized in the triphenylamine structure. The LUMO was almost localized in the perylene part. Therefore, the ground-state absorption of TFPA is mainly attributed to the π–π* transition accompanied by with little the slight intramolecular charge transfer effect. The maximum emission peak (534 nm) of TFPA in the solid state was 18 nm redshifted compared to that of TFPA in solution (516 nm). TG results show that TFPA still does not decompose at 300 ℃, indicating good thermal stability. In addition, a yellow-light-emitting diode device based on the fluorescent molecule TFPA was constructed (CIE coordinates: 0.45, 0.54). The LED device showed good color purity (color purity: 97.8%). The results showed that TFPA was a luminescent material with excellent thermal stability and high color purity and had potential for use in fabricating yellow LEDs.
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References
Alvarez-Venicio V, Arcos-Ramos RO et al (2019) Preparation and characterization of a novel organic semiconductor indacenedithiophene derivative and the corresponding langmuir-blodgett thin films. J Nanosci Nanotechnol 19(11):7244–7250. https://doi.org/10.1166/jnn.2019.17129
Changmin K, David B, Emily A et al (2020) Organic light-emitting diodes based on a columnar liquid-crystalline perylene emitter. Adv Opt Mater 8:2000414. https://doi.org/10.1002/adom.202000414
Duan S, Gao X, Wang Y et al (2019) Scalable fabrication of highly crystalline organic semiconductor thin film by channel-restricted screen printing toward the low-cost fabrication of high-performance transistor arrays. Adv Mater 31(16):1807975. https://doi.org/10.1002/adma.201807975
Guijarro FG, Malhotra P, Gupta G et al (2020) The influence of the terminal acceptor and oligomer length on the photovoltaic properties of A-D–A small molecule donors. J Mater Chem C 8(14):4763–4770. https://doi.org/10.1039/d0tc00154f
Gupta RK, Sudhakar AA (2019) Perylene-based liquid crystals as materials for organic electronics applications. Langmuir 35:2455. https://doi.org/10.1021/acs.langmuir.8b01081
Gupta SK, Setia S, Sidiq S et al (2013) New perylene-based non-conventional discotic liquid crystals. RSC Adv 3:12060. https://doi.org/10.1039/c3ra41186a
Hasebe N, Suzuki K, Horiuchi H, Suzuki H et al (2015) Absolute phosphorescence quantum yields of singlet molecular oxygen in solution determined using an integrating sphere instrument. Anal Chem 87:2360–2366. https://doi.org/10.1021/ac5042268
Huang X, Guo H, Li B et al (2017) Eu3+-activated Na2Gd(PO4)(MoO4): a novel high-brightness red-emitting phosphor with high color purity and quantum efficiency for white light-emitting diodes. J Alloy Compd 720:29–38. https://doi.org/10.1016/j.jallcom.2017.05.251
Jiang Y, Li YF, Li YQ et al (2015) Realization of high-luminous-efficiency InGaN light-emitting diodes in the “green gap” range. Sci Rep 5(1):10883. https://doi.org/10.1038/srep10883
Jiang F, Zhang JL, Xu LQ et al (2019) Efficient InGaN-based yellow-light-emitting diodes. Photonics Res 7(2):144–148. https://doi.org/10.1364/PRJ.7.000144
Jose LM, Maximilienne B, Canek FH et al (2003) Effect of substitution on the hole mobility of bis(diarylamino)biphenyl derivatives doped in poly(styrene). Chem Mater 15:994–999. https://doi.org/10.1021/cm0207907
Khoury M, Li HJ, Li PP et al (2020) Polarized monolithic white semipolar (20–21) InGaN light-emitting diodes grown on high quality (20–21) GaN/sapphire templates and its application to visible light communication. Nano Energy 67:104236. https://doi.org/10.1016/j.nanoen.2019.104236
Koutsiaki C, Kaimakamis T, Zachariadis A et al (2019) Efficient combination of roll-to-roll compatible techniques towards the large area deposition of a polymer dielectric film and the solution-processing of an organic semiconductor for the field-effect transistors fabrication on plastic substrate. Org Electron 73:231–239. https://doi.org/10.1016/j.orgel.2019.06.010
Kovalenko MV, Protesescu L, Bodnarchuk MI et al (2017) Properties and potential optoelectronic applications of lead halide perovskite nanocrystals. Science 358(6364):745–750. https://doi.org/10.1126/science.aam7093
Li ZF, Wu ZX, Fu W et al (2012) Versatile fluorinated derivatives of triphenylamine as hole transporters and blue-violet emitters in organic light-emitting devices. J Phys Chem C 116(38):20504–20512. https://doi.org/10.1021/jp3028929
Marcel G, David B, Huang LZ et al (2016) Organic semiconductors based on dyes and color pigments. Adv Mater 28:3615–3645. https://doi.org/10.1002/adma.20150544
Neumann A, Wierer J, Davis W et al (2011) Four-color laser white illuminant demonstrating high color-rendering quality. Opt Express 19(S4):A982–A990. https://doi.org/10.1364/OE.19.00A982
Pawel C, Christian S, Georg G (2011) Hole Transport in triphenylamine based OLED devices: from theoretical modeling to properties prediction. J Phys Chem A 115:14519–14525. https://doi.org/10.1021/jp207585j
Pimputkar S, Speck J, Denbaars S et al (2009) Prospects for LED lighting. Nat Photonics 3(4):180–182. https://doi.org/10.1038/nphoton.2009.32
Satyam KG, Shilpa S, Sumyra S et al (2013) New perylene-based non-conventional discotic liquid crystals. RSC Adv 3:12060–12065. https://doi.org/10.1039/C3RA41186A
Shi ZF, Xu TT, Wu D et al (2016) Semi-transparent all-oxide ultraviolet light-emitting diodes based on ZnO/NiO-core/shell nanowires. Nanoscale 8(19):9997–10003. https://doi.org/10.1039/c5nr07236k
Veldhuis SA, Boix PP, Yantara N et al (2016) Perovskite materials for light-emitting diodes and lasers. Adv Mater 28(32):6804–6834. https://doi.org/10.1002/adma.20160066
Wang J, Chu M, Fan JX et al (2019) Crystal engineering of biphenylene-containing acenes for high-mobility organic semiconductors. J Am Chem Soc 141(8):3589–3596. https://doi.org/10.1021/jacs.8b12671
Wei YX, Wang Y, Zhou QH et al (2020) Solvent effects on triplet–triplet annihilation upconversion kinetics of perylene with a Bodipy-phenyl-C60 photosensitizer. Phys Chem Chem Phys 22(45):26372–26382. https://doi.org/10.1039/d0cp04230g
Wright TH, Bower BJ, Chalker JM et al (2016) Posttranslational mutagenesis: a chemical strategy for exploring protein side-chain diversity. Science 354(6312):1465. https://doi.org/10.1126/science.aag1465
Wu DB, Gong WJ, Yao HM et al (2020) Highly efficient solid-state emission of diphenylfumaronitriles with full-color AIE, and application in explosive sensing, data storage and WLEDs. Dyes Pigm 172:107829. https://doi.org/10.1016/j.dyepig.2019.107829
Würthner F (2020) Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem Commun 4:1564. https://doi.org/10.1039/b401630k
Zhao D, Zhang Z, Li C et al (2020) Yellow-emitting hydrophobic carbon dots via solid-phase synthesis and their applications. ACS Omega 5(35):22587–22595. https://doi.org/10.1021/acsomega.0c03239
Zhu TH, He GK, Chang J et al (2012) The synthesis, photophysical and electrochemical properties of a series of novel 3, 8, 13-substituted triindole derivatives. Dyes Pigm 95:679–688. https://doi.org/10.1016/j.dyepig.2012.06.011
Zhu YL, Liang YJ, Liu SQ et al (2018) Design of hierarchical composite silicate for full-color and high thermal stability phosphors. Chem Eng J 345:327–336. https://doi.org/10.1016/j.cej.2018.03.182
Acknowledgements
The authors greatly acknowledge the Natural Science Foundation of Jiangsu Province (BK20170104), Jiangsu Planned Projects for Postdoctoral Research Funds, “Six Talent Peaks Project” of Jiangsu Province (XCL-037) Postgraduate Research & Practice Innovation Program of Jiangsu Province (KYCX21-1183, KYCX21-1185, KYCX21-1186) for financial support. The computational resources generously provided by the High Performance Computing Center of Nanjing Tech University are greatly appreciated.
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Shi, H., Meng, R., Zhu, S. et al. Diarylamino-substituted perylene compound: synthesis, fluorescence, and application in yellow LEDs. Chem. Pap. 75, 6455–6463 (2021). https://doi.org/10.1007/s11696-021-01806-5
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DOI: https://doi.org/10.1007/s11696-021-01806-5