Abstract :

The present computational work deals with the Quinacridone green dopant theoretical organic light emitting diode molecule has been carried out with density functional theory by using Gaussian09 package. All the quantum chemical calculations have been performed with HF, B3LYP and B3PW91 functional methods. The structural parameter, bond topological analysis and the corresponding electrostatic and transport properties of the OLED molecule has been calculated. The laplacian of electron density and bond ellipticity of molecule have been studied for various optimized methods. The atomic charges of the molecule for different optimized methods has been analysed with AIM, MPA and NPA charges. The HLG of the molecule are calculated from different optimized basis sets. The HF method value is 8.49 eV. The B3LYP and B3PW91 methods energy values are 3.13 eV and 3.12 eV respectively. These values are most equal to the energy gap obtained from density of states (DOS) spectrum. Hence, the ESP shows that expend of O-atoms and the charge accumulated through Quinacridone OLED molecule. The grateful Quinacridone green dopant derivative molecule is high quantum efficiency, longer lifetime and very useful to industrial organic pigment of these molecules.

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Keywords :

AIM, DFT, ESP, HLG, OLED.

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References :

1. Squires R, A.D. Lewis Adam A. Zaczek J and Timothy Korter M, (2017), Distinguishing Quinacridone Pigments via Terahertz Spectroscopy: Absorption Experiments and Solid-State Density Functional Theory Simulations, Journal of Physical Chemistry A, 121 (18): 3423-3429.
2. Struve WS. (1958), US Patent 2. 844.485.
3. Studies in Quinacridone Chemistry. DuPont Innovation, 2: 14-17. Editorial office: DuPont Building, Wilmington, Delaware 19898, USA. (1970).
4. Labana SS, Labana LL, (1967), Quinacridone. Chemical Reviews, 67 (1), 1-18.
5. Weiping Chen, Kui Tian, Xiaoxian Song, Zuolun Zhang,  Kaiqi Ye, Gui Yu and Yue Wang, (2015), Large π‑Conjugated Quinacridone Derivatives: Syntheses, Characterizations, Emission, and Charge Transport Properties, Organic Letters, 17 (24), 6146–6149.
6. Koezuka, H.; Tsumura, A.; Ando, T. (1987), “Field-effect transistor with polythiophene thin film”. Synthetic Metals. 18 (1-3), 699–704.
7. Kafafi Z. H, Murata H, Picciolo L.C, Mattoussi H, Merritt C.D, Iizumi Y, Kido J, (1999), Electroluminescent properties of functional Π-electron molecular systems, Pure Applied Chemistry, 71 (11), 2085-2094.
8. Shaheen S.E, Kippelen B, Peyghambarian N, Wang J.F, Anderson J.D, Mash E.A, Lee P.A, Armstrong N.R, Kawabe Y., (1999), Energy and charge transfer in organic light-emitting diodes: A soluble quinacridone study, Journal of Applied Physics. 85 (11), 7939-7945.
9. Tang C.W, VanSlyke S.A, Chen C.H, (1989), Electroluminescence of doped organic thin films, Journal of Applied Physics, 65 (9), 3610-3616.
10. Shi J, Tang C.W, (1997), Doped organic electroluminescent devices with improved stability, Applied Physics Letter, 70 (13), 1665-1667.
11. Kundu S, Fujihara K, Okada T, Matsumura M, (2000), Excitation Migration from Photoexcited Tris(8-hydroxyquinolino)aluminium to Quinacridone in Codeposited Thin Films, Japanese Journal of Applied Physics, 39, 5297.
12. Hung L.S, Chen C.H, (2002), Recent progress of molecular organic electroluminescent materials and devices, Materials Science. Engineering, R: Reports, 39 (5-6), 143-222.
13. Hamada Y, Sano T, Shibata K, Kuroko K, (1995), Influence of the Emission Site on the Running Durability of Organic Electroluminescent Devices, Japanese Journal of Applied Physics, 34 L824 – L826.
14. Berggren M, Dodabalapur A, Slusher R.E, (1997), Applied Physics Letter, 71 (16), 2230-2232.
15. Tsujimura T. OLED Display Fundamentals and Applications (Wiley Series in Display Technology). Wiley-VCH. (2012).
16. Paulus E. F, Leusen F. J. J, and Schmidt M. U, (2007), “Crystal structures of quinacridone”, Crystal Engineering Communications, 9, (2), 131–143.
17. Lincke G, (2000), “A review of thirty years of research on quinacridone. X-ray crystallography and crystal engineering”, Dyes and Pigments, 44, (2), 101–122.
18. Mateusz Barczewski, Danuta Matykiewicz, and Bart Bomiej Hoffmann, (2017), ‘Effect of Quinacridone Pigments on Properties and Morphology of Injection Molded Isotactic Polypropylene’ International Journal of Polymer Science, 2017, 1-8,
19. Duan L, Hou L, Lee T.W, Qiao J, Zhang D, Dong G, Wang L, Qiu Y, (2010), Solution processable small molecules for organic light-emitting diodes, Journal of Material Chemistry, 20 (31), 6392-6407.
20. Puschnig P, Reinisch E.M, Ules T, Koller G, Soubatch S, Ostler M, Romaner L, Tautz F. S, Ambrosch-Draxl C, and Ramsey M. G, (2011), ‘Orbital tomography: Deconvoluting photoemission spectra of organic molecules’ Physical Review, B 84, 235427.
21. Seminario J.M, Politzer P, (1995), Moleculer Density Functional theory: A tool for Chemistry, Elsevier, New York.
22. Wadt W.R, Hay P.J, (1985), Journal of Chemical Physics, 284:
23. J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K.Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al- Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. 47 Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople, Gaussian Inc, P. A. Pittsburgh, (2003).
24. Schlegel B, (1982), Journal of Computational Chemistry, 3, 214.
25. AIMAll (Version 10.03.25) Todd A. Keith (aim.tkgristmill.com), (2010).
26. Tsirelson S.V, WinXPRO, (2002), A program for calculating crystal and molecular properties using multipole parameters of the electron density, Journal of Applied Crystallography, 35, 371–373.
27. Frish A, Lecn E, Nielson A.B, Holder A, Roy Dennigton A.J, Keith T.A, Gaussian Incorporated, Pittsburgh PA, (2003).

28. Boyle N.O, GaussSum, Revision 2.1, http://GaussSum.sf.net.
29. Joseph, S. Comins, D. L. (2002), Current Opinion in Drug Discovery and Development, 5, 870.
30. Schmidt R, (1965), Chemische Berichte, 98,334.
31. Fisyuk A.S, Vorontsova M.A, and Ivanov S.A, (1994), Novel Synthesis of 5,6-dihydropyridin-4(3H)-one, Chemistry of Heterocyclic compounds, 30, (6)
32. David Stephen A., Srinivasan P., Kumaradhas P., (2011), Bond Charge Depletion, Bond Strength and the Impact Sensitivity of High Energetic 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB) Molecule: A Theoretical Charge Density Analysis, Comput. Theo. Chem., 967, 250-256.
33. F.W. Bader, (1990), Atoms in Molecule; A Quantum theory, Clarendon Press, Oxford, UK.
34. Popelier P.L.A, (1999), Atom in Molecules an Introduction, Pearson Edition, Harlow, UK.
35. Seminario J. M and Politzer P, (1995), Molecular Density Functional Theory: A Tool for Chemistry, Elesvier, New York.
36. Arputharaj David Stephen, Reji Thomas, Ponnusamy Srinivasan, Vijayan Narayayanasamy, Poomani Kumaradhas, (2011), Exploring the bond topological and electrostatic properties of benzimidazole molecule via experimental and theoretical charge density study Journal of Molecular Structure, 989, 122–130.
37. Dudek A.Z, Arodz T, Galvez J, (2006), Computational methods in developing quantitative structure-activity relationships (QSAR): a review. Comb Chem High Throughput Screen (3):213–228.
38. Beck H.P, (2015), A DFT study on the correlation between topology and Bader charges: part I, effects of compression and expansion of As2O5, Solid State Sci. 41, 1-7.
39. Beck H.P, (2015), A DFT study on the correlation between topology and Bader charges: part II, effects of compression and expansion of V2O5, Solid State Sci. 43, 1-8.
40. Beck H.P, (2015), A study on AB2O6 compounds, part V: a DFT study on charge balance as driving force for structural organization, Z. Krist. 7, 449 – 458.
41. Reed, E., R.B. Weinstock, and F. Weinhold, (1985), Natural population analysis, The Journal of Chemical Physics, 83(2), 735-746.
42. Slattery D. K, Linkous C. A, Gruhn N. E, and Baum J, (2001), Dyes Pigments, 49, 21.
43. Daniel Luftner, Sivan Refaely-Abramson, Michael Pachler, Roland Resel, Michael G. Ramsey, Leeor Kronik, and Peter Puschnig, (2014), Experimental and theoretical electronic structure of quinacridone, PHYSICAL REVIEW B 90, 075204-1-10.
44. Prasad M.V.S, Chaitanya K, UdayaSri N, Veeraiah V, (2013), Experimental and theoretical (HOMO, LUMO, NBO analysis and NLO properties) study of 7-hydroxy-4-phenylcoumarin and 5,7-dihydroxy-4-phenylcoumarinJournal of Molecular Structure 1047, 216–228.
45. Subramanian Palanisamy, Ponnusamy Srinivasan, Aruputharaj David Stephen and Karuppannan Selvaraju, (2018), Charge Density and Electrical Characteristics of 1,2-di([1,1′-biphenyl]-4-yl)ethyne (DBPE) Molecular Nanowire by Quantum Chemical Study, Journal of Computational Theoretical Nanoscience, Vol. 15, No. 5, 1516–1527.