journal article·2022-05

NIR-OLED structures based on lanthanide coordination compounds: synthesis and luminescent properties

Artem Barkanov, Anna Zakharova, Tatjana Vlasova, Ekaterina Barkanova, Andrew Khomyakov, Igor Avetissov, Ilya Taydakov, Nikolay Datskevich, Victoria Goncharenko, Roman Avetisov

Journal of Materials Science· Volume 57· Issue 18
Publisher page

Abstract

Electroluminescence complexes based on ytterbium and 5-methyl-2-phenyl-4-(2,2,2-trifluoroacetyl)-2,4-dihydro-3H-pyrazol-3-one (HL) ligand and various diimine-type ancillary ligands (2,2-bipyridine, bathophenanthroline, 1,10-phenanthroline) have been synthesized, and corresponding crystals were investigated. [Yb(L)3(bipy)] and [Yb(L)3(bath)] complexes have triclinic structure (P-1), while [Yb(L)3(phen)] complex has orthorhombic structure (P212121). The crystallography parameters were determined. The photoluminescence of the complexes demonstrated only bands resulted from $$2 F5/2^{{}} o2 F7/2^{{}}$$ transition and corresponding three Stark subcomponents generated due to the crystal field action. NIR-OLED structures with emitting layers based on the [Yb(L)3(bipy)], [Yb(L)3(bath)], and [Yb(L)3(phen)] complexes have been fabricated, and their electroluminescence demonstrated maxima intensities at 978 and 1005 nm. Comparison of NIR-OLEDs power density showed that the maximal power densities of 2.17 (978 nm) and 1.92 (1005 nm) μW × cm−2 were determined for the NIR-OLED based on [Yb(L)3(bath)] complex.
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Research context

OpenAlex topics: Lanthanide and Transition Metal Complexes · Magnetism in coordination complexes · Organic Light-Emitting Diodes Research

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

References (48)

Show source-provided references
1. ISO 20473 (2007) Optics and photonics — Spectral bands
2. Minotto A, Haigh PA, Łukasiewicz ŁG, Lunedei E, Gryko DT, Darwazeh I, Cacialli F (2020) Visible light communication with efficient far-red/near-infrared polymer light-emitting diodes. Light Sci Appl 9(1):1–11. https://doi.org/10.1038/s41377-020-0314-z10.1038/s41377-020-0314-z ↗
3. Lochner CM (2018) Printed organic light emitting diodes for biomedical applications. Doctoral dissertation, UC Berkeley
4. Smith AM, Mancini MC, Nie S (2009) Second window for in vivo imaging. Nat Nanotechnol 4(11):710–711. https://doi.org/10.1038/nnano.2009.32610.1038/nnano.2009.326 ↗
5. Cao M, Wang X, Zhang M et al (2019) Electromagnetic response and energy conversion for functions and devices in low-dimensional materials. Adv Funct Mater 29:1807398. https://doi.org/10.1002/adfm.20180739810.1002/adfm.201807398 ↗
6. Yao L-H, Cao W-Q, Shu J-C et al (2021) Tailoring adsorption for tunable lithium ion storage and devices. Chem Eng J 413:127428. https://doi.org/10.1016/j.cej.2020.12742810.1016/j.cej.2020.127428 ↗
7. Zhang Y, Qiao J (2021) Near-infrared emitting iridium complexes: molecular design, photophysical properties, and related applications. iScience 24:102858. https://doi.org/10.1016/j.isci.2021.10285810.1016/j.isci.2021.102858 ↗
8. Zysman-Colman E (ed) (2017) Iridium (III) in optoelectronic and photonics applications. John Wiley & Sons, Hoboken
9. Ly KT, Chen-Cheng RW, Lin HW, Shiau YJ, Liu SH, Chou PT, Tsao C-S, Huang Y-C, Chi Y (2017) Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance. Nat Photonics 11(1):63–68. https://doi.org/10.1038/nphoton.2016.23010.1038/nphoton.2016.230 ↗
10. Pushkarev AP, Bochkarev MN (2016) Organic electroluminescent materials and devices emitting in UV and NIR regions. Russ Chem Rev 85:1338–1368. https://doi.org/10.1070/RCR466510.1070/RCR4665 ↗
11. Fu G, Guan J, Li B et al (2018) An efficient and weak efficiency-roll-off near-infrared (NIR) polymer light-emitting diode (PLED) based on a PVK-supported Zn 2+ –Yb 3+ -containing metallopolymer. J Mater Chem C 6:4114–4121. https://doi.org/10.1039/C7TC05400A10.1039/C7TC05400A ↗
12. Bünzli J-CG (2015) On the design of highly luminescent lanthanide complexes. Coord Chem Rev 293–294:19–47. https://doi.org/10.1016/j.ccr.2014.10.01310.1016/j.ccr.2014.10.013 ↗
13. Santos HP, Gomes ES, dos Santos MV et al (2019) Synthesis, structures and spectroscopy of three new lanthanide β-diketonate complexes with 4,4′-dimethyl-2,2′-bipyridine. Near-infrared electroluminescence of ytterbium(III) complex in OLED. Inorganica Chim Acta 484:60–68. https://doi.org/10.1016/j.ica.2018.09.03010.1016/j.ica.2018.09.030 ↗
14. Taydakov IV, Zaitsev BE, Krasnoselskiy SS, Starikova ZA (2011) Synthesis, X-ray structure and luminescent properties of Sm3+ ternary complex with novel heterocyclic β-diketone and 1,10-phenanthroline (Phen). J Rare Earths 29:719–722. https://doi.org/10.1016/S1002-0721(10)60529-710.1016/S1002-0721(10)60529-7 ↗
15. Metlin MT, Ambrozevich SA, Metlina DA et al (2017) Luminescence of pyrazolic 1,3-diketone Pr3+ complex with 1,10-phenanthroline. J Lumin 188:365–370. https://doi.org/10.1016/J.JLUMIN.2017.04.05810.1016/J.JLUMIN.2017.04.058 ↗
16. Taidakov IV, Zaitsev BE, Lobanov AN et al (2013) Synthesis and luminescent properties of neutral Eu(III) and Gd(III) complexes with 1-(1,5-dimethyl-1h-pyrazol-4-yl)-4,4,4-trifluoro-1,3-butanedione and 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)-1,3-hexanedione. Russ J Inorg Chem 58:411–415. https://doi.org/10.1134/S003602361304019010.1134/S0036023613040190 ↗
17. Metlina DA, Metlin MT, Ambrozevich SA et al (2018) Luminescence and electronic structure of Nd3+ complex with pyrazole-substituted 1,3-diketone and 1,10-phenanthroline. J Lumin 203:546–553. https://doi.org/10.1016/J.JLUMIN.2018.07.00510.1016/J.JLUMIN.2018.07.005 ↗
18. Gontcharenko VE, Kiskin MA, Dolzhenko VD et al (2021) Mono- and Mixed Metal Complexes of Eu3+, Gd3+, and Tb3+ with a Diketone, Bearing Pyrazole Moiety and CHF2-Group: structure, color tuning, and kinetics of energy transfer between lanthanide ions. Molecules 26:2655. https://doi.org/10.3390/molecules2609265510.3390/molecules26092655 ↗
19. Taydakov IV, Belousov YA, Lyssenko KA et al (2020) Synthesis, phosphorescence and luminescence properties of novel europium and gadolinium tris-acylpyrazolonate complexes. Inorganica Chim Acta 502:119279. https://doi.org/10.1016/j.ica.2019.11927910.1016/j.ica.2019.119279 ↗
20. George TM, Varughese S, Reddy MLP (2016) Near-infrared luminescence of Nd 3+ and Yb 3+ complexes using a polyfluorinated pyrene-based β-diketonate ligand. RSC Adv 6:69509–69520. https://doi.org/10.1039/C6RA12220E10.1039/C6RA12220E ↗
21. Reid BL, Stagni S, Malicka JM et al (2014) Lanthanoid β-triketonates: a new class of highly efficient NIR emitters for bright NIR-OLEDs. Chem Commun 50:11580–11582. https://doi.org/10.1039/C4CC04961F10.1039/C4CC04961F ↗
22. Zhang Z, Yu C, Liu L et al (2016) Efficient near-infrared (NIR) luminescent PMMA-supported hybrid materials doped with tris-β-diketonate Ln3+ complex (Ln=Nd or Yb). J Photochem Photobiol A Chem 314:104–113. https://doi.org/10.1016/j.jphotochem.2015.08.02210.1016/j.jphotochem.2015.08.022 ↗
23. Marchetti F, Pettinari C, Pettinari R et al (2002) A new family of ionic dinuclear strontium (imH2)2[Sr2(Q)6] compounds (imH = imidazole; QH = 1-phenyl-3-methyl-4-acylpyrazol-5-one). J Chem Soc Dalt Trans. https://doi.org/10.1039/b200189f10.1039/b200189f ↗
24. Zhang X, Liu L, Yu C et al (2016) Highly efficient near-infrared (NIR) luminescent tris- β -diketonate Yb 3+ complex in solution and in PMMA. Inorg Chem Commun 70:153–156. https://doi.org/10.1016/j.inoche.2016.06.00610.1016/j.inoche.2016.06.006 ↗
25. Cecchini MM, De Angelis F, Iacobucci C et al (2016) Mild catalytic oxidations of unsaturated fatty acid methyl esters (FAMEs) by oxovanadium complexes. Appl Catal A Gen 517:120–128. https://doi.org/10.1016/j.apcata.2016.01.04510.1016/j.apcata.2016.01.045 ↗
26. Marchetti F, Pettinari C, Pettinari R et al (2000) Influence of sterically demanding groups on the structure and stability in the solid and solution state of (acylpyrazolonate)bis(phosphine)copper(I) derivatives. Inorganica Chim Acta 299:65–79. https://doi.org/10.1016/S0020-1693(99)00463-610.1016/S0020-1693(99)00463-6 ↗
27. Golubev AS, Tyutin VY, Chkanikov ND et al (1992) Reactions of highly electrophilic polyfluoro unsaturated compounds with pyrazole derivatives. Bull Russ Acad Sci Div Chem Sci 41:2068–2073. https://doi.org/10.1007/BF0086337510.1007/BF00863375 ↗
28. Marchetti F, Pettinari C, Cingolani A et al (1999) Tin(IV) and organotin(IV) derivatives of novel β-diketones. J Organomet Chem 580:344–353. https://doi.org/10.1016/S0022-328X(98)01173-510.1016/S0022-328X(98)01173-5 ↗
29. Bovio B, Cingolani A, Marchetti F, Pettinari C (1993) Tin(IV) and organotin(IV) complexes containing the anion of some substituted-3-methyl-4-acyl-5-pyrazolones. Crystal structure of dimethylbis(1-phenyl-3-methyl-4-benzoyl pyrazolon-5-ato)tin(IV). J Organomet Chem 458:39–48. https://doi.org/10.1016/0022-328X(93)80455-K10.1016/0022-328X(93)80455-K ↗
30. Okafor EC (1981) The metal complexes of heterocyclic β-diketones and their derivatives, part viii synthesis, structure, proton nmr and infrared spectral studies of the complexes of Al(III), Fe(III), Co(III), Rh(III), In(III), and Zr(IV) with l-phenyl-3-methyl-4-trifluoroa. Zeitschrift für Naturforsch B 36:213–217. https://doi.org/10.1515/znb-1981-021710.1515/znb-1981-0217 ↗
31. Marchetti F, Pettinari C, Pettinari R et al (2007) Areneruthenium(II) 4-Acyl-5-pyrazolonate derivatives: coordination chemistry, redox properties, and reactivity. Inorg Chem 46:8245–8257. https://doi.org/10.1021/ic700394r10.1021/ic700394r ↗
32. Nagar MS, Ruikar PB, Subramanian MS (1988) Complexes of tetravalent plutonium, uranium and thorium with acylpyrazolones. Inorganica Chim Acta 141:309–312. https://doi.org/10.1016/S0020-1693(00)83925-010.1016/S0020-1693(00)83925-0 ↗
33. Deruiter J, Carter DA, Arledge WS, Sullivan PJ (1987) Synthesis and reactions of 4-isopropylidene-1-aryl-3-methyl-2-pyrazolin-5-ones. J Heterocycl Chem 24:149–153. https://doi.org/10.1002/jhet.557024012810.1002/jhet.5570240128 ↗
34. Sheldrick GM (2015) SHELXT—Integrated space-group and crystal-structure determination. Acta Crystallogr Sect A Found Adv 71:3–8. https://doi.org/10.1107/S205327331402637010.1107/S2053273314026370 ↗
35. Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Crystallogr Sect C Struct Chem 71:3–8. https://doi.org/10.1107/S205322961402421810.1107/S2053229614024218 ↗
36. Dolomanov OV, Bourhis LJ, Gildea RJ et al (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr 42:339–341. https://doi.org/10.1107/S002188980804272610.1107/S0021889808042726 ↗
37. Jensen BS, Meier H, Lundquist K, Refn S (1959) The Synthesis of 1-Phenyl-3-methyl-4-acyl-pyrazolones-5. Acta Chem Scand 13:1668–1670. https://doi.org/10.3891/acta.chem.scand.13-166810.3891/acta.chem.scand.13-1668 ↗
38. Buckley A (2013) Organic light-emitting diodes (OLEDs): materials, devices and applications, 1st edn. Woodhead Publishing, Sawston10.1533/9780857098948 ↗
39. So F (2010) Organic electronics: materials, processing devices and applications. CRC Press, Francis and Taylor, Boca Raton
40. Bünzli J-CG, Eliseeva SV (2010) Basics of lanthanide photophysics. In: Hänninen P, Härmä H (eds) Lanthanide luminescence. Springe, Berlin, pp 1–45
41. Carnall WT, Fields PR, Rajnak K (1968) Electronic energy levels of the trivalent lanthanide Aquo Ions. II. Gd 3+. J Chem Phys 49:4443–4446. https://doi.org/10.1063/1.166989410.1063/1.1669894 ↗
42. Faustino WM, Malta OL, Teotonio EES et al (2006) Photoluminescence of europium(iii) dithiocarbamate complexes: electronic structure, charge transfer and energy transfer. J Phys Chem A 110:2510–2516. https://doi.org/10.1021/jp056180m10.1021/jp056180m ↗
43. Korshunov VM, Ambrozevich SA, Taydakov IV et al (2019) Novel β-diketonate complexes of Eu3+ bearing pyrazole moiety for bright photo- and electroluminescence. Dye Pigment 163:291–299. https://doi.org/10.1016/j.dyepig.2018.12.00610.1016/j.dyepig.2018.12.006 ↗
44. Metlin MT, Goryachii DO, Aminev DF et al (2021) Bright Yb3+ complexes for efficient pure near-infrared OLEDs. Dye Pigment 195:109701. https://doi.org/10.1016/j.dyepig.2021.10970110.1016/j.dyepig.2021.109701 ↗
45. Rogozhin AF, Silantyeva LI, Yablonskiy AN et al (2021) Near infrared luminescence of Nd, Er and Yb complexes with perfluorinated 2-mercaptobenzothiazolate and phosphine oxide ligands. Opt Mater (Amst) 118:111241. https://doi.org/10.1016/j.optmat.2021.11124110.1016/j.optmat.2021.111241 ↗
46. Taydakov IV, Akkuzina AA, Avetisov RI et al (2016) Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety. J Lumin 177:31–39. https://doi.org/10.1016/j.jlumin.2016.04.01710.1016/j.jlumin.2016.04.017 ↗
47. Li Z, Zhang H, Yu J (2012) Near-infrared electroluminescence from double-emission-layers devices based on Ytterbium (III) complexes. Thin Solid Films 520(9):3663–3667. https://doi.org/10.1016/j.tsf.2011.12.05210.1016/j.tsf.2011.12.052 ↗
48. Yersin H (2007) Highly efficient OLEDs with phosphorescent materials. Wiley-VCH Verlag GmbH & Co KGaA, Weinheim10.1002/9783527621309 ↗