Year

2019

Type(s)

Journal Article

Author(s)

Chapran, M. and Lytvyn, R. and Begel, C. and Wiosna-Salyga, G. and Ulanski, J. and Vasylieva, M. and Volyniuk, D. and Data, P. and Grazulevicius, J.V.

Source

Dyes and Pigments, 162: 872—882, 2019

Url

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85056639707&doi=10.1016%2fj.dyepig.2018.11.022&partnerID=40&md5=97388046496c6c359d9e5807675ea1c9

BibTeX

BibTeX

BibTeX

@ARTICLE{Chapran2019872, author={Chapran, M. and Lytvyn, R. and Begel, C. and Wiosna-Salyga, G. and Ulanski, J. and Vasylieva, M. and Volyniuk, D. and Data, P. and Grazulevicius, J.V.}, title={High-triplet-level phthalimide based acceptors for exciplexes with multicolor emission}, journal={Dyes and Pigments}, year={2019}, volume={162}, pages={872-882}, doi={10.1016/j.dyepig.2018.11.022}, note={cited By 7}, url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-85056639707&doi=10.1016%2fj.dyepig.2018.11.022&partnerID=40&md5=97388046496c6c359d9e5807675ea1c9}, affiliation={Lodz University of Technology, Department of Molecular Physics, Zeromskiego 116, Lodz, 90-924, Poland; Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu Plentas 19, Kaunas, LT-50254, Lithuania; Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv, 79005, Ukraine; Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, Gliwice, 44-100, Poland; Department of Physics, Durham University, South Road, Durham, DH1 3LE, United Kingdom}, abstract={To provide high exciton utilization in organic light emitting diodes, phthalimide derivatives were designed and synthesized as exciplex-forming materials. Due to high triplet levels (2.92–3.11 eV) and ionization potentials (7.18–7.29 eV), the developed phthalimide derivatives were found to be not only appropriate accepting materials for the formation of different color exciplexes but also as bifunctional materials with a satisfactory hole and exciton-blocking abilities. Solid-state blends of the synthesized phthalimides as acceptors and a carbazole containing donors showed exciplex emission. Bimolecular blends exhibited multicolor exciplex emission which covered a visible spectrum from sky-blue to red colors, depending on the donor used. However, the photoluminescence quantum efficiencies of the studied exciplex-forming systems were found to be sensitive to the molecular design of the phthalimides. Acceptor with para-substituted phthalimide showed better exciplex-forming properties in comparison to other compounds. Exciplex-forming blend of (2-(4-benzoylphenyl)isoindoline-1,3-dione) as an acceptor and 1,3-di(9H-carbazol-9-yl)benzene (mCP) as a donor showed the most efficient sky-blue emission with small singlet-triplet splitting (0.06 ± 0.03eV). Such exciplex-forming molecular mixture was implemented as the light-emitting material in the sky-blue organic light emitting diodes which showed the brightness of 2500 cd m−2 and maximum external quantum efficiency of 2.9% due to the employment of both singlet and triplet excitons. © 2018}, author_keywords={Acceptors; Exciplex; Organic light emitting diode (OLED); Phthalimide; Thermally activated delayed fluorescence (TADF)}, keywords={Efficiency; Electronic equipment; Excitons; Fluorescence; Ionization potential; Luminance; Organic light emitting diodes (OLED); Organic polymers, Acceptors; Blue organic light emitting diodes; Exciplexes; External quantum efficiency; Photoluminescence quantum efficiency; Phthalimide; Singlet and triplet excitons; Thermally activated delayed fluorescences, Quantum efficiency, Diodes; Efficiency; Electronic Equipment; Emission; Fluorescence; Forming; Light; Materials}, funding_details={Lietuvos Mokslo TarybaLietuvos Mokslo Taryba, S-MIP-17-101}, funding_details={Horizon 2020 Framework ProgrammeHorizon 2020 Framework Programme, H2020, 674990}, funding_text 1={The authors would like to acknowledge the EXCILIGHT project funded by the European Union’s Horizon 2020 Research and Innovation Programme under grant agreement No. 674990 . This work was also supported by Research Council of Lithuania (Project “OWEX” No S-MIP-17-101 ). Special acknowledgement to prof. Tadeusz Biela for mass spectrometry analysis.}, references={Hatakeyama, T., Shiren, K., Nakajima, K., Nomura, S., Nakatsuka, S., Kinoshita, K., Ni, J., Ikuta, T., Ultrapure blue thermally activated delayed fluorescence molecules: efficient HOMO-LUMO separation by the multiple resonance effect (2016) Adv Mater, 28, pp. 2777-2781; Reineke, S., Lindner, F., Schwartz, G., Seidler, N., Walzer, K., Lüssem, B., Leo, K., White organic light-emitting diodes with fluorescent tube efficiency (2009) Nature, 459, pp. 234-238; Uoyama, H., Goushi, K., Shizu, K., Nomura, H., Adachi, C., Highly efficient organic light-emitting diodes from delayed fluorescence (2012) Nature, 492, pp. 234-238; Wong, M.Y., Zysman-Colman, E., Purely organic thermally activated delayed fluorescence materials for organic light-emitting diodes (2017) Adv Mater, 29, p. 1605444; Wu, T.-L., Huang, M.-J., Lin, C.-C., Huang, P.-Y., Chou, T.-Y., Chen-Cheng, R.-W., Lin, H.-W., Cheng, C.-H., Diboron compound-based organic light-emitting diodes with high efficiency and reduced efficiency roll-off (2018) Nat Photon, 12, pp. 235-240; Goushi, K., Yoshida, K., Sato, K., Adachi, C., Organic light-emitting diodes employing efficient reverse intersystem crossing for triplet-to-singlet state conversion (2012) Nat Photon, 6, pp. 253-258; Sarma, M., Wong, K.-T., Exciplex: an intermolecular charge-transfer approach for TADF (2018) ACS Appl Mater Interfaces, 10, pp. 19279-19304; Cocchi, M., Virgili, D., Sabatini, C., Kalinowski, J., Organic electroluminescence from singlet and triplet exciplexes: exciplex electrophosphorescent diode (2006) Chem Phys Lett, 421, pp. 351-355; Graves, D., Jankus, V., Dias, F.B., Monkman, A., Photophysical investigation of the thermally activated delayed emission from films of m-MTDATA:PBD exciplex (2014) Adv Funct Mater, 24, pp. 2343-2351; Hung, W.-Y., Fang, G.-C., Lin, S.-W., Cheng, S.-H., Wong, K.-T., Kuo, T.-Y., Chou, P.-T., The first tandem, all-exciplex-based WOLED (2015) Sci Rep, 4, p. 5161; Chapran, M., Angioni, E., Findlay, N.J., Breig, B., Cherpak, V., Stakhira, P., Tuttle, T., Skabara, P.J., An ambipolar BODIPY derivative for a white exciplex OLED and cholesteric liquid crystal laser toward multifunctional devices (2017) ACS Appl Mater Interfaces, 9, pp. 4750-4757; Cherpak, V., Stakhira, P., Minaev, B., Baryshnikov, G., Stromylo, E., Helzhynskyy, I., Chapran, M., Grazulevicius, J.V., Efficient “Warm-White” OLEDs Based on the Phosphorescent bis-Cyclometalated iridium(III) Complex (2014) J Phys Chem C, 118, pp. 11271-11278; Liu, X.-K., Chen, Z., Qing, J., Zhang, W.-J., Wu, B., Tam, H.L., Zhu, F., Lee, C.-S., Remanagement of singlet and triplet excitons in single-emissive-layer hybrid white organic light-emitting devices using thermally activated delayed fluorescent blue exciplex (2015) Adv Mater, 27, pp. 7079-7085; Lee, J.-H., Shin, H., Kim, J.-M., Kim, K.-H., Kim, J.-J., Exciplex-forming Co-Host-Based red phosphorescent organic light-emitting diodes with long operational stability and high efficiency (2017) ACS Appl Mater Interfaces, 9, pp. 3277-3281; Etherington, M.K., Franchello, F., Gibson, J., Northey, T., Santos, J., Ward, J.S., Higginbotham, H.F., Monkman, A.P., Regio- and conformational isomerization critical to design of efficient thermally-activated delayed fluorescence emitters (2017) Nat Commun, 8, p. 14987; Jankus, V., Data, P., Graves, D., McGuinness, C., Santos, J., Bryce, M.R., Dias, F.B., Monkman, A.P., Highly efficient TADF OLEDs: how the emitter-host interaction controls both the excited state species and electrical properties of the devices to achieve near 100% triplet harvesting and high efficiency (2014) Adv Funct Mater, 24, pp. 6178-6186; Dias, F.B., Santos, J., Graves, D.R., Data, P., Nobuyasu, R.S., Fox, M.A., Batsanov, A.S., Monkman, A.P., The role of local triplet excited states and D-A relative orientation in thermally activated delayed fluorescence: photophysics and devices (2016) Adv Sci, 3, p. 1600080; Yang, X., Xu, X., Zhou, G., Recent advances of the emitters for high performance deep-blue organic light-emitting diodes (2015) J Mater Chem C, 3, pp. 913-944; Tao, Y., Yang, C., Qin, J., Organic host materials for phosphorescent organic light-emitting diodes (2011) Chem Soc Rev, 40, p. 2943; Yu, J., Yang, J., Zhou, X., Yu, S., Tang, Y., Wang, H., Chen, J., Guo, X., Phthalimide-based wide bandgap donor polymers for efficient non-fullerene solar cells (2017) Macromolecules, 50, pp. 8928-8937; Xin, H., Guo, X., Kim, F.S., Ren, G., Watson, M.D., Jenekhe, S.A., Efficient solar cells based on a new phthalimide-based donor–acceptor copolymer semiconductor: morphology, charge-transport, and photovoltaic properties (2009) J Mater Chem, 19, p. 5303; Zhang, G., Guo, J., Zhang, J., Li, P., Ma, J., Wang, X., Lu, H., Qiu, L., A phthalimide- and diketopyrrolopyrrole-based A 1 –π–A 2 conjugated polymer for high-performance organic thin-film transistors (2015) Polym Chem, 6, pp. 418-425; Lee, S.-H., Khim, D., Xu, Y., Kim, J., Park, W.-T., Kim, D.-Y., Noh, Y.-Y., Simultaneous improvement of hole and electron injection in organic field-effect transistors by conjugated polymer-wrapped carbon nanotube interlayers (2015) Sci Rep, 5, p. 10407; Dumur, F., Ibrahim-Ouali, M., Gigmes, D., Organic light-emitting diodes based on phthalimide derivatives: improvement of the electroluminescence properties (2018) Appl Sci, 8, p. 539; Jang, M.E., Yasuda, T., Lee, J., Lee, S.Y., Adachi, C., Organic light-emitting diodes based on donor-substituted phthalimide and maleimide fluorophores (2015) Chem Lett, 44, pp. 1248-1250; Srinivas, S., Caputo, F.E., Graham, M., Gardner, S., Davis, R.M., McGrath, J.E., Wilkes, G.L., Semicrystalline polyimides based on controlled molecular weight phthalimide end-capped 1,3-Bis(4-aminophenoxy)benzene and 3,3‘,4,4‘-biphenyltetracarboxylic dianhydride: synthesis, crystallization, melting, and thermal stability (1997) Macromolecules, 30, pp. 1012-1022; Li, M., Li, S.-H., Zhang, D., Cai, M., Duan, L., Fung, M.-K., Chen, C.-F., Stable enantiomers displaying thermally activated delayed fluorescence: efficient OLEDs with circularly polarized electroluminescence (2018) Angew Chem Int Ed, 57, pp. 2889-2893; Venkatramaiah, N., Kumar, G.D., Chandrasekaran, Y., Ganduri, R., Patil, S., Efficient blue and yellow organic light-emitting diodes enabled by aggregation-induced emission (2018) ACS Appl Mater Interfaces, 10, pp. 3838-3847; Li, M., Liu, Y., Duan, R., Wei, X., Yi, Y., Wang, Y., Chen, C.-F., Aromatic-imide-based thermally activated delayed fluorescence materials for highly efficient organic light-emitting diodes (2017) Angew Chem Int Ed, 56, pp. 8818-8822; Chapman, J.M., Voorstad, P.J., Cocolas, G.H., Hall, I.H., Hypolipidemic activity of phthalimide derivatives. 2. N-Phenylphthalimide and derivatives (1983) J Med Chem, 26, pp. 237-243; Cardona, C.M., Li, W., Kaifer, A.E., Stockdale, D., Bazan, G.C., Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications (2011) Adv Mater, 23, pp. 2367-2371; Data, P., Pander, P., Lapkowski, M., Swist, A., Soloducho, J., Reghu, R.R., Grazulevicius, J.V., Unusual properties of electropolymerized 2,7- and 3,6- carbazole derivatives (2014) Electrochim Acta, 128, pp. 430-438; Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., Gaussian 09, revision A.02 Wallingford, CT (2009); Gawronski, J., Kazmierczak, F., Gawronska, K., Rychlewska, U., Nordén, B., Holmén, A., Excited states of the phthalimide chromophore and their exciton couplings: a tool for stereochemical assignments (1998) J Am Chem Soc, 120, pp. 12083-12091; Lakowicz, J.R., (2006) Principles of fluorescence spectroscopy, , Springer US Boston, MA; Pander, P.H., Gogoc, S., Colella, M., Data, P., Dias, F.B., Thermally-activated delayed fluorescence in polymer-small molecule exciplex blends for solution-processed organic light-emitting diodes (2018) ACS Appl Mater Interfaces, 10, pp. 28796-28802; Liu, W., Chen, J.-X., Zheng, C.-J., Wang, K., Chen, D.-Y., Li, F., Dong, Y.-P., Zhang, X.-H., Novel strategy to develop exciplex emitters for high-performance OLEDs by employing thermally activated delayed fluorescence materials (2016) Adv Funct Mater, 26, pp. 2002-2008; Kim, K.-H., Yoo, S.-J., Kim, J.-J., Boosting triplet harvest by reducing nonradiative transition of exciplex toward fluorescent organic light-emitting diodes with 100% internal quantum efficiency (2016) Chem Mater, 28, pp. 1936-1941; Tsierkezos, N.G., Investigation of the electrochemical reduction of benzophenone in aprotic solvents using the method of cyclic voltammetry (2007) J Solut Chem, 36, pp. 1301-1310; Zamani, H.A., PVC-membrane potentiometric electrochemical sensor based on 2-(4-Oxopentan-2-ylideneamino)isoindoline-1,3-dione for selective determination of holmium(III) (2011) E-Journal Chem., 8, pp. S97-S104; Kalinowski, J., Cocchi, M., Virgili, D., Fattori, V., Williams, J.A.G., Mixing of excimer and exciplex emission: a new way to improve white light emitting organic electrophosphorescent diodes (2007) Adv Mater, 19, pp. 4000-4005; Gordon, M., Ware, W.R., (1975) The exciplex, , Academic Press; Kalinowski, J., Excimers and exciplexes in organic electroluminescence (2009) Mater Sci, 27, pp. 735-756; Pander, P., Kudelko, A., Brzeczek, A., Wroblowska, M., Walczak, K., Data, P., Analysis of exciplex emitters (2017) Disp Imaging, 2, pp. 265-277; Dias, F.B., Kinetics of thermal-assisted delayed fluorescence in blue organic emitters with large singlet-triplet energy gap (2015) Philos Trans R Soc A Math Phys Eng Sci, 373. , 20140447–20140447; dos Santos, P.L., Dias, F.B., Monkman, A.P., Investigation of the mechanisms giving rise to TADF in exciplex states (2016) J Phys Chem C, 120, pp. 18259-18267; Seino, Y., Inomata, S., Sasabe, H., Pu, Y.-J., Kido, J., High-performance green OLEDs using thermally activated delayed fluorescence with a power efficiency of over 100 lm W −1 (2016) Adv Mater, 28, pp. 2638-2643; Hung, W., Wang, T., Chiang, P., Peng, B., Wong, K., Remote steric effect as a facile strategy for improving the efficiency of exciplex-based OLEDs (2017) ACS Appl Mater Interfaces, 9, pp. 7355-7361; Su, S.-J., Chiba, T., Takeda, T., Kido, J., Pyridine-containing triphenylbenzene derivatives with high electron mobility for highly efficient phosphorescent OLEDs (2008) Adv Mater, 20, pp. 2125-2130; Tsutsui, T., Progress in electroluminescent devices using molecular thin films (1997) MRS Bull, 22, pp. 39-45}, correspondence_address1={Grazulevicius, J.V.; Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu Plentas 19, Lithuania; email: juozas.grazulevicius@ktu.lt}, publisher={Elsevier Ltd}, issn={01437208}, coden={DYPID}, language={English}, abbrev_source_title={Dyes Pigm.}, document_type={Article}, source={Scopus},