Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Tin(IV) Complexes with 8-hydroxyquinoline Ligand Derivatives as Precursors for the Manufacture of Organic Light-Emitting Diodes

Document Type : Research Article

Authors
Ezzatollah Najafi 1
Mohammad Janghouri 2
Hamid Abedi 3
1 Faculty of Chemistry, Payam Noor University, Tehran, Iran
2 Faculty of Industrial Technologies, Urmia University of Technology, Urmia, Iran
3 Police Equipment and Technologies Research Institute, Police Science and Social Studies Research Institute, Tehran, Iran
Abstract
Five 8-hydroxyquinoline complexes of tin were prepared by reacting diphenyltin dichloride with 8-hydroxyquinoline and its derivatives for using as fluorescent materials in organic light-emitting diodes (OLEDs). The elemental analysis and IR, UV–vis, 1H and 119Sn NMR spectroscopes were used to characterize the prepared compounds. The details and features of the reaction were described and discussed. The prepared compounds were utilized as the green-yellow EL dopant materials to fabricate OLED devices with a general configuration of ITO/PEDOT:PSS(90 nm)/PVK:PBD:tin-complex(80 nm)/Al(200 nm). PVK (polyvinyl carbazole) and PBD (2-(4-Biphenylyl)-5-phenyl-1,3,4-oxadiazole) as hole-transporting and electron-transporting materials, respectively, were doped within tin compounds as the emissive layer. The results of the investigation of electroluminescent (EL) and photoluminescence (PL) properties of prepared complex showed that the electron donating or withdrawing substituent groups on 8-hydroxyquinoline have a significant effect on the tuning and changing of emission wavelengths.
Keywords
Diphenyltin(IV) Complex
Photoluminescence
Electroluminescence
OLED

Subjects

[1] Kim S., Lee J.I., Yang J., Shin I.-S., Earmme T., Kang M.S., A Guide for Realizing Efficient Polymer Light-Emitting Electrochemical Cells in a Single Active Layer Device Structure. Chem. Electro. Chem., 7(1): 260-265 (2020).
[2] Meier S.B., Tordera D., Pertegás A., Roldán-Carmona C., Ortí E., Bolink H.J., Light-Emitting Electrochemical Cells: Recent Progress and Future Prospects. Mater. Today,, 17(5): 217-223 (2014).
[3] Matsuki K., Pu J., Takenobu T., Recent Progress on Light-Emitting Electrochemical Cells with Nonpolymeric Materials. Adv. Funct. Mater., 30(33): 1908641 (2020).
[4] Kwon D.K., Myoung J.-M., Ion Gel-Based Flexible Electrochemiluminescence Full-Color Display with Improved Sky-Blue Emission Using a Mixed-Metal Chelate System. Chem. Eng. J., 379: 122347 (2020).
[5] Meng X., Wang P., Bai R., He L., Blue-Green-Emitting Cationic Iridium Complexes with Oxadiazole-Type Counter-Anions and Their use for Highly Efficient Solution-Processed Organic Light-Emitting Diodes. J. Mater. Chem. C, 8(18): 6236-6244 (2020).
[6] Chahkandi M., Theoretical Investigation of Non-Covalent Interactions and Spectroscopic Properties of a New Mixed-Ligand Co(II) Complex. J. Mol. Struct. 1111(5): 193–200 (2016).
 [7] Chahkandi M., 51V NMR, 17O NMR, and UV–Vis Computational Studies of New VBPO Functional Models: Bromide Oxidation Reaction. Polyhedron, 109(18): 92-98(2016).
 [8] Chahkandi M., Khoshbakht B. M., Mirzaei M., A Theoretical Study of Intramolecular H–Bonding and Metal–Ligandinteractions in Some Complexes with Bicyclic Guanidine Ligands. Comput. Theor. Chem. 1095: 36-43 (2016).
 [9] Chahkandi M., Mirzaei, Structural and Particle Size Evolution of Sol–Gel-Derived Nanocrystalline Hydroxyapatite. J. Iran. Chem. Soc. 14: 567-575 (2017).
 [10] Chahkandi M., Aliabad H.A.R., Evaluation of  Non-covalent Binding Energiesand Optoelectronic Properties of New CuBr2(C6H7N)2 Complex: DFT Approaches,Z. Anorg. Allg. Chem. 643(2): 180-191 (2017).
 [11] Yunus U., Ahmed S., Chahkandi M., Bhatti M. H., Nawaz Tahir M., Synthesis and Theoretical Studies of Non‒Covalent Interactions within a Newly Synthesized Chiral 1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazine.J. Mol. Struct. 1130(15): 688-698 (2017).
 [6] Singh D., Nishal V., Bhagwan S., Saini R. K., Singh I., Electroluminescent Materials: Metal Complexes of 8-Hydroxyquinoline - A review. Mater. Des., 156: 215-228 (2018).
[7] Wang T.T., Zeng G.-C., Zeng H.P., Liu P.Y., Wang R.X., Zhang Z.J., Xiong Y.L., Synthesis of Light-Emmting Materials Bis-[2′-2″-(9H-Fluoren-2-yl)-Vinyl-8-Hydroxyquinoline] Zinc(II) and Bis-[2′-4″-(4,5-Diphenyl-1H-Imidazol-2-yl)Styryl-8-Hydroxyquinoline] Zinc(II). Tetrahedron, 65(32): 6325-6329 (2009).
[8] Yang X., Xu X., Zhou G., Recent Advances of the Emitters for High Performance Deep-Blue Organic Light-Emitting Diodes. J. Mater. Chem. C, 3(5): 913-944 (2015).
[9] Miao Y., Tao P., Wang K., Li H., Zhao B., Gao L., Wang H., Xu B., Zhao Q., Highly Efficient Red and White Organic Light-Emitting Diodes with External Quantum Efficiency Beyond 20% by Employing Pyridylimidazole-Based Metallophosphors. ACS Appl. Mater. Interfaces, 9(43): 37873-37882 (2017).
[10] Shen Z., Burrows P.E., Bulović V., Forrest S.R., Thompson M.E., Three-Color, Tunable, Organic Light-Emitting Devices. Science, 276(5321): 2009-2011 (1997).
[11] D'Andrade B. W., Forrest S.R., White Organic Light-Emitting Devices for Solid-State Lighting. Adv. Mater., 16(18): 1585-1595 (2004).
[12] Bai R., Meng X., Wang X., He L., Blue-Emitting Iridium(III) Complexes for Light-Emitting Electrochemical Cells: Advances, Challenges, and Future Prospects. Adv. Funct. Mater., 30(33): 1907169 (2020).
[13] Frohleiks J., Wepfer S., Bacher G., Nannen E., Realization of Red Iridium-Based Ionic Transition Metal Complex Light-Emitting Electrochemical Cells (iTMC-LECs) by Interface-Induced Color Shift. ACS Appl. Mater.Interfaces, 11(25): 22612-22620 (2019).
[14] Lee S., Han W.-S., Cyclometalated Ir (III) Complexes Towards Blue-Emissive Dopant for Organic Light-Emitting Diodes: Fundamentals of Photophysics and Designing Strategies. Inorg. Chem. Front., 7(12): 2396-2422 (2020).
[15] Allendorf M.D., Bauer C.A., Bhakta R.K., Houk R.J.T., Luminescent Metal–Organic Frameworks. Chem. Soc. Rev., 38(5): 1330-1352 (2009).
[16] امیدیان ر.، عظیمی غ.، عباسی م.، مطالعه نظری ساختار هندسی و الکترونی مشتق­ های 1,4 ـ بیس(دیفنیل‌آمینو)بنزن) و بررسی کارآمدی این ترکیب­ ها به عنوان ماده انتقال حفره در دیودهای نورگسیل آلی (OLED). نشریه شیمی و مهندسی شیمی ایران, 39(1): 73-90 (1399)
[17] Bünzli J.C.G., Eliseeva S.V., Basics of Lanthanide Photophysics. In P. Hänninen,  H. Härmä (Eds.), Lanthanide Luminescence: Photophysical, Analytical and Biological Aspects, Berlin, Heidelberg: Springer Berlin Heidelberg 1-45 (2011).
[18]Chahkandi M., Bhatti M.H., Yunus U., Shaheen S., Nadeem M., Tahir M. N., Synthesis and Comprehensive Structural Studies of a Novel Amide Based Carboxylic Acid Derivative: Non–Covalent Interactions. J. Mol. Struct. 1133: 499-509 (2017).
[19] Rahnamaye Aliabad H.A., Chahkandi M., Comprehensive SPHYB and B3LYP-DFT Studies of Two Types of Ferrocene. Z. Anorg. Allg. Chem. 643(6): 420-431 (2017).
[20] Rahnamaye Aliabad H.A., Chahkandi M., Optoelectronic and Structural Studies of a Ni(II) Complex Including Bicyclic Guanidine Ligands: DFT Calculations. Comput. Theor. Chem. 1122: 53-61 (2017).
 [21] Chahkandi M., Bhatti M. H., Yunus U., Rehman N., Nadeem M., Tahir M. N., Zakria M., Novel Cocrystal of N-Phthaloyl-b-Alanine with 2,2ebipyridyl: Synthesis, Computational and Free Radical Scavenging Activity Studies, J. Mol. Struct. 1152: 1-10 (2018).
 [22] Rahmati Z., Mirzaei M.,  Chahkandi M., Mague J.T., Accurate DFT Studies on Crystalline Network Formation of a New Co(II) Complex Bearing 8-Aminoquinoline. Inorg. Chim. Acta. 473: 152-159 (2018).
[23] Chahkandi M., Rahnamaye Aliabad H.A., Role of Hydrogen Bonding in Establishment of a Crystalline .Network of Cu (II) Complex with Hydrazon-Derived Ligand: Optoelectronic Studies. Chem. Pap. 72: 1287-97 (2018).
[24] Rahnamaye Aliabad H.A., Chahkandi M., Theoretical Study of Crystalline Network and Optoelectronic Properties of Erlotinib Hydrochloride Molecule: Non-Covalent Interactions Consideration. Chem. Pap. 73: 737-46 (2019).
[25] Chahkandi M., Bhatti M.H., Yunus U., Nadeem M., Rehman N., Nawaz Tahir M., Crystalline Network Study of New N-Phthaloyl-b-ALANINE with Benzimidazole, Cocrystal: Computational Consideration & Free Radicalscavenging Activity. J. Mol. Struct. 1191: 225-236 (2019).
[26] Chahkandi M., Keivanloo Shahrestanaki A., Mirzaei M., Tahir M.N., Mague J.T., Crystal and Molecular Structure of [Ni(2-H2NC(=O)C5H4N)2(H2O)2][Ni(2,6-(O2C)2C5H3N)2]×4.67H2O; DFT Studies on Hydrogen Bonding Energies in the Crystal, Acta Crystallogr., Sect. B. B76: 591-603 (2020).
[27] Oh C.S., Lee J.Y., High Triplet Energy Al Complex as a Host Material for Blue Phosphorescent Organic Light-Emitting Diodes. Org. Electron., 15(5): 1071-1075 (2014).
[28] Solanki J.D., Siddiqui I., Gautam P., Gupta V. K., Jou J.-H., Surati K.R., Blue Fluorescent Zinc(II) Complexes Bearing Schiff Base Ligand for Solution-Processed Organic Light-Emitting Diodes with CIEy ≤ 0.09.Opt. Mater.,, 134: 113222 (2022).
[29] Najafpour J., Modulating Band Gap and HOCO/LUCO Energy of Boron-Nitride Nanotubes under a Uniform External Electric Field. Iran. J. Chem. Chem. Eng., 36(6): 93-106 (2017).
[30] Najafi E., Amini M.M., Janghouri M., Mohajerani E., Ng S.W., Effects of the π-Conjugation Length of Bipyridyl Ligand on the Photophysical Properties of Binuclear Organotin(IV) Complexes: Synthesis and Characterization of Dimethyltin(IV) Complexes with Bipyridyl. Inorganica Chim. Acta, 415: 52-60 (2014).
[31] Hodaie M., Sadjadi M.S., Amini M.M., Najafi E., Ng S.W., Sonochemical Synthesis of a Nanocrystalline Tin(IV) Complex based on a Bulky Anthracene Carboxylate Ligand: Spectroscopic and Photophysical Properties. J. Inorg. Organomet. Polym. Mater., 26(3): 500-511 (2016).
[32] Behzad S.K., Najafi E., Amini M.M., Janghouri M., Mohajerani E., Ng S.W., Yellow-Green Electroluminescence of Samarium Complexes of 8-Hydroxyquinoline. J. Lumin..,156: 219-228 (2014).
[33] Rezaei S.J.T., Norouzi K., Hesami A., Malekzadeh A.M., Ramazani A., Amani V., Ahmadi R., Au(III) Complexes Loaded pH-Responsive Magnetic Nanogels for Cancer Therapy.Appl. Organomet. Chem. 32(4): 1-10 (2018).
[34] Ahmadi R., Kalateh K., Amani, V., Catena-Poly[[(5,5′-Dimethyl-2,2′-bi-Pyridine- κ2 N,N′)Cadmium(II)]-di-μ-Iodido]. Acta Crystallogr., Sect. E: Struct. Rep. Online. 66: m562-m562 (2010).
[35] Amani V.,  Ahmadi R., Naseh M., Ebadi A., Synthesis, Spectroscopic Characterization, Crystal Structure and Thermal Analyses of Two zinc(II) Complexes with Methanolysis of 2-Pyridinecarbonitrile as a Chelating Ligand. J. Iran. Chem. Soc. 14: 635-642 (2017).
[36] Rezaei T., Khorramabadi S.J., Hesami H., Ramazani A., Amani V., Ahmadi R., Chemoselective Reduction of Nitro and Nitrile Compounds with Magnetic Carbon Nanotubes-Supported Pt(II) Catalyst under Mild Conditions. Ind. Eng. Chem. Res. 56(43): 12256-12266 (2017).
[37] Kalateh K., Ahmadi R., Amani V. (4,4′-Dimethyl-2,2′-Bipyridineκ2 N,N′)(Dimethyl sulfoxideκO) Diiodidocadmium(II). Acta Crystallogr., Sect. E: Struct. Rep. Online. E66: m512-520 (2010).  
 [38] Janghouri M., Mohajerani E., Amini M.M., Najafi E., Green–white Electroluminescence and Green Photoluminescence of Zinc Complexes. J. Lumin.,, 154: 465-474 (2014).
[39] Tang C.W., Slyke S.A.V., Organic Electroluminescent Diodes. Appl. Phys. Lett.,51: 913-915 (1987).
[40]Adachi C., Tsutsui T., Saito S., Blue Light-Emitting Organic Electroluminescent Devices. Appl. Phys. Lett. 57: 799-801 (1990).
[41] Hamada Y., in Organic Electroluminescent Materials and Devices, Editedby S. Miyata and H. S. Nalwa-Gordon and Breach, Amsterdam, 311-334 (1997).
[42] Burrows P. E., Sapochak L.S., Mccarty D.M., Forrest S.R., Thompson M.E., Metal ion Dependent Luminescence Effects in Metal Tris‐Quinolate Organic Heterojunction Light Emitting Devices.Appl. Phys. Lett. 64: 2718-2720 (1994).
[43] Tao X.T., Suzuki H., Wada T., Miyata S., Sasabe H., Lithium Tetra-(8-Hydroxy-Quinolinato) Boron for Blue Electroluminescent Applications.Appl. Phys. Lett. 75: 1655-1657 (1999).
[44]  Tao X.T.,  Shimomura M.,  Suzuki H., Miyata S., Sasabe H., Tetravalent tin Complex with High Electron Affinity for Electroluminescent Applications. Appl. Phys. Lett. 76: 3522-3524 (2000).
[45] Armanego W.L.F., Purification of Laboratory Chemicals, Eighth Edition., Butterworth-Heinemann. New York (2017).
 [46] Najafi E.,   Kheirkhahi M.,   Amini M.M., Ng S.W., Preparation of SnO2 Nanoparticles from a New Tin(IV) Complex: Spectroscopic and Photoluminescence Studies.J Inorg Organomet Polym. 23:1015-1022(2013).
[47]  Amini M.M.,  Najafi E., Saeidian H.,  Mohammadi E.,  Shahabi S.M.,  Ng S.W., Effect of Pseudohalogen Groups on the Optical Properties and the Structures of Diorganotin Coordination Compounds Based on the Flexible Ligand 1,2,3,4-Tetra-(4-Pyridyl)-Butane, Appl Organometal Chem. 31: e3884-3892(2017).
 [48] Najafi E., Amini M.M., Ng S.W., (2-Methylquinolin-8-Olato-[Kappa]2N,O)Diphenyl (Thiocyanato-[Kappa]N)Tin(IV). Acta Crystallogr. E, 66(2): m164 (2010).
[49] Linden A., Basu Baul T.S., Mizar A., cis-Bis(8-Hydroxyquinolinato-[Kappa]2N,O) Diphenyltin(IV). Acta Crystallogr. E, 61(1): m27-m29 (2005).
[50] Wang J.J., Liu C.S., Hu T.L., Chang Z., Li C.Y., Yan L.F., Chen P.Q., Bu X.H., Wu Q., Zhao L.J., Wang Z., Zhang X.Z., Zinc(II) Coordination Architectures with Two Bulky Anthracene-Based Carboxylic Ligands: Crystal Structures and Luminescent Properties. Cryst. Eng. Comm., 10(6): 681-692 (2008).
[51]  Eaton D.F., Reference Materials for Fluorescence Measurement. Pure Appl. Chem., 60: 11 07-1 114 (1988).
[52] Ma B., Kim B.J., Deng L., Poulsen D. A., Thompson M.E., Fréchet J.M.J., Bipolar Copolymers as Host for Electroluminescent Devices:  Effects of Molecular Structure on Film Morphology and Device Performance. Macromolecules, 40(23): 8156-8161 (2007).
[53] Yang J., Gordon K.C., Electroluminescence of Ruthenium(II)(4,7-Diphenyl-1,10-Phenanthroline)3 from Charge Trapping by Doping in Carrier-Transporting Blend Films. Chem. Phys. Lett., 385(5): 481-485 (2004).
[54] Chang S.M., Fan C.H., Lai C.C., Chao Y.C., Hu S.C., Red Electroluminescence from RUTHENIUM Complexes. Surf. Coat. Technol., 200(10): 3289-3296 (2006).
[55] Galanin M.D., Luminescence of Molecules and Crystals. Cambridge: Cambridge International Science Publishing, 69-80 (1996).