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Synthesis, crystal structure, photoluminescence, and electroluminescence properties of a new compound containing diphenylmethylene, carbazole, and malononitrile units

Published online by Cambridge University Press:  10 June 2019

Zhaofeng Shi ,
Dayong Zhang ,
Jinnan Huo ,
Hongbo Wang ,
Junsheng Yu ,
Heping Shi  and
Ben Zhong Tang
Zhaofeng Shi*
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Dayong Zhang
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Jinnan Huo
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Hongbo Wang
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Junsheng Yu*
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Heping Shi*
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Ben Zhong Tang*
Affiliation:
Department of Chemistry, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology, Kowloon, Hong Kong 999077, China
*
a)Address all correspondence to these authors. e-mail: [email protected]
b)e-mail: [email protected]
c)e-mail: [email protected]
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Abstract

In this work, a new phenylethylene derivative, named 2-((3,5-di(9H-carbazol-9-yl)phenyl)(p-tolyl)methylene)malononitrile (DCPTMM), is synthesized and characterized by 1H NMR, 13C NMR spectroscopies, mass spectrum, and X-ray crystallography. Its photophysical properties are systematically studied and the result illustrates that DCPTMM shows aggregation-induced emission (AIE). The X-ray single crystal diffraction shows that the individual structure of crystals is monoclinic system with space group symbol P21/c and presents a twisted propeller-type structure as well as the packing structure of crystals has multiple types of hydrogen bonds (C–H⋯π and C–H⋯N) formed between adjacent molecules, and there is no π–π interaction between the aromatic rings, which is the main reason for the formation of AIE. Nondoped OLED fabricated with DCPTMM as light emitting layer emits greenish yellow light with a maximum emission peak of 554 nm and has relatively good performance with a maximum current efficiency of 5.53 cd/A and a maximum brightness of 6936 cd/m2.

Keywords

chemical synthesiscrystallographic structureoptical properties
Type
Article
Information
Journal of Materials Research , Volume 34 , Issue 17: Focus Issue: Building Advanced Materials via Particle Aggregation and Molecular Self-Assembly , 16 September 2019 , pp. 3000 - 3010
Copyright
Copyright © Materials Research Society 2019 

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References

Tang, C.W. and VanSlyke, S.A.: Organic electroluminescent diodes. Appl. Phys. Lett. 51, 913–915 (1987).CrossRefGoogle Scholar
Adachi, C., Tokito, S., Tsutsui, T., and Saito, S.: Electroluminescence in organic films with three-layer structure. J. Appl. Phys. 27, L269–L271 (1988).CrossRefGoogle Scholar
Burroughes, J.H., Bradley, D.D.C., Brown, A.R., Marks, R.N., Mackay, K., Friend, R.H., Burns, P.L., and Holmes, A.B.: Light-emitting diodes based on conjugated polymers. Nature 347, 539–541 (1990).CrossRefGoogle Scholar
Tao, X.T., Suzuki, H., Wada, T., Suzuki, H., and Miyata, S.: Lithium tetra-(8-hydroxy-quinolinato) boron for blue electroluminescent application. Appl. Phys. Lett. 75, 1655–1657 (1999).CrossRefGoogle Scholar
Xiao, L.X., Chen, Z.J., Brown, A.R., Bo, Q., Luo, J.X., Kong, S., Gong, Q.H., and Kiod, J.J.: Recent progresses on materials for electrophosphorescent organic light-emitting devices. Adv. Mater. 23, 926–952 (2011).CrossRefGoogle ScholarPubMed
Li, J., Ma, C., Tang, J., Lee, C.S., and Lee, S.: Novel starburst molecule as a hole injecting and transporting material for organic light-emitting devices. Chem. Mater. 17, 615–619 (2005).CrossRefGoogle Scholar
Li, J., Liu, D., Li, Y., Lee, C.S., Kwong, H., and Lee, S.: A high Tg carbazole-based hole-transporting material for organic light-emitting devices. Chem. Mater. 17, 1208–1212 (2005).CrossRefGoogle Scholar
Bernius, M.T., Inbasekaran, M., O’Brien, J.J., and Wu, W.: Progress with light-emitting polymers. Adv. Mater. 12, 1737–1749 (2000).3.0.CO;2-N>CrossRefGoogle Scholar
Thomas, S.W. III, Joly, G.D., and Swager, T.M.: Chemical sensors based on amplifying fluorescent conjugated polymers. Chem. Rev. 107, 1339–1386 (2007).CrossRefGoogle ScholarPubMed
Chiang, C-L., Tseng, S-M., Chen, C-T., Hsu, C-P., and Shu, C-F.: Influence of molecular dipoles on the photoluminescence and electr-luminescence of dipolar spirobifluorenes. Adv. Funct. Mater. 18, 248–257 (2008).CrossRefGoogle Scholar
Wang, J., Zhao, Y., Dou, C., Sun, H., Xu, P., Ye, K., Zhang, J., Jiang, S., Li, F., and Wang, Y.: Alkyl and dendron substituted quinacridones: Synthesis, structures, and luminescent properties. J. Phys. Chem. B 111, 5082–5089 (2007).CrossRefGoogle ScholarPubMed
Grimsdale, A.C., Chan, K.L., Martin, R.E., Jokisz, P.G., and Holmes, A.B.: Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chem. Rev. 109, 897–1091 (2009).CrossRefGoogle ScholarPubMed
Liu, J.Z., Lam, J.W.Y., and Tang, B.Z.: Acetylenic polymers: Syntheses, structures, and functions. Chem. Rev. 109, 5799–5867 (2009).CrossRefGoogle ScholarPubMed
Luo, J.D., Xie, Z.L., Lam, J.W.Y., Cheng, L., Chen, H.Y., Qiu, C.F., Kwok, H.S., Zhan, X.W., Liu, Y.Q., Zhu, D.B., and Tang, B.Z.: Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun. 18, 1740–1741 (2001).CrossRefGoogle Scholar
Chen, J., Xu, B., Ouyang, X.Y., Tang, B.Z., and Cao, Y.: Aggregation-induced emission of cis,cis-1,2,3,4-tetraphenylbutadiene from restricted intramolecular rotation. J. Phys. Chem. A 108, 7522–7526 (2004).CrossRefGoogle Scholar
Leung, N.L.C., Xie, N., Yuan, W., Liu, Y., Wu, Q., Peng, Q., Miao, Q., Lam, J.W.Y., and Tang, B.Z.: Restriction of intramolecular motions: The general mechanism behind aggregation-induced emission. Chem.–Eur. J. 20, 15349–15353 (2014).CrossRefGoogle ScholarPubMed
Hong, Y., Lam, J.W.Y., and Tang, B.Z.: Aggregation-induced emission. Chem. Soc. Rev. 40, 5361e5388 (2011).CrossRefGoogle ScholarPubMed
Mei, J., Hong, Y., Lam, J.W.Y., Qin, A., and Tang, B.Z.: Aggregation-induced emission: The whole is more brilliant than the parts. Adv. Mater. 26, 5429–5459 (2014).CrossRefGoogle Scholar
Wang, H., Zhao, E., Lam, J.W.Y., and Tang, B.Z.: AIE luminogens: Emission brightened by aggregation. Mater. Today 7, 365–377 (2015).CrossRefGoogle Scholar
Zhao, Z.J., He, B.R., and Tang, B.Z.: Aggregation-induced emission of siloles. Chem. Mater. 6, 5347–5365 (2015).Google ScholarPubMed
Liang, J., Liu, B., and Tang, B.Z.: Specific light-up bioprobes based on AIEgen conjugates. Chem. Soc. Rev. 44, 2798–2811 (2015).CrossRefGoogle ScholarPubMed
Kwok, T.K., Leung, C.W.T., Chris, W.T., Lam, J.W.Y., and Tang, B.Z.: Biosensing by luminogens with aggregation-induced emission characteristics. Chem. Soc. Rev. 44, 4228–4238 (2015).CrossRefGoogle ScholarPubMed
Mei, J., Hong, Y.N., Lam, J.W.Y., Qin, A.J., Tang, Y.H., and Tang, B.Z.: Aggregation-induced emission: The whole is more brilliant than the parts. Adv. Mater. 26, 5429–5479 (2014).CrossRefGoogle Scholar
Hu, G.R., Lelson, N.L.C., and Tang, B.Z.: AIE macromolecules: Syntheses, structures and functionalities. Chem. Soc. Rev. 43, 4494–4562 (2014).CrossRefGoogle ScholarPubMed
Dong, Y.Q., Li, C.Y., Zhao, W.J., Dong, Y.P., and Tang, B.Z.: Stimulus responsive luminescent materials: Crystallization-induced emission enhancement. J. Mol. Eng. Mater. 1, 1340010/1–1340010/13 (2013).CrossRefGoogle Scholar
Ding, D., Li, K., Liu, B., and Tang, B.Z.: Bioprobes based on AIE fluorogens. Acc. Chem. Res. 46, 2441–2453 (2013).CrossRefGoogle ScholarPubMed
Zhao, Z.J., Lam, J.W.Y., and Tang, B.Z.: Self-assembly of organic luminophores with gelation-enhanced emission characteristics. Soft Matter 9, 4564–4579 (2013).CrossRefGoogle Scholar
Zhao, Z.J., Lam, J.W.Y., and Tang, B.Z.: Tetraphenylethene: A versatile AIE building block for the construction of efficient luminescent materials for organic light-emitting diodes. J. Mater. Chem. 22, 23726–23740 (2012).CrossRefGoogle Scholar
Qin, A.J., Lam, J.W.Y., and Tang, B.Z.: Luminogenic polymers with aggregation-induced emission characteristics. Prog. Polym. Sci. 37, 182–209 (2012).CrossRefGoogle Scholar
Hong, Y.N., Lam, J.W.Y., and Tang, B.Z.: Aggregation-induced emission. Chem. Soc. Rev. 40, 5361–5388 (2011).CrossRefGoogle ScholarPubMed
Hong, Y.N., Lam, J.W.Y., and Tang, B.Z.: Aggregation-induced emission: Phenomenon, mechanism and applications. Chem. Commun. 29, 4332–4353 (2009).CrossRefGoogle Scholar
Huang, J., Sun, N., Chen, P.Y., Tang, R.L., Li, Q.Q., Ma, D.G., and Li, Z.: Largely blue-shifted emission through minor structural modifications: Molecular design, synthesis, aggregation-induced emission and deep-blue OLED application. Chem. Commun. 50, 2136–2138 (2014).CrossRefGoogle ScholarPubMed
Huang, J., Sun, N., Yang, J., Tang, R.L., Li, Q.Q., Ma, D.G., and Li, Z.: Blue aggregation-induced emission luminogens: High external quantum efficiencies up to 3.99% in LED device, and restriction of the conjugation length through rational molecular design. Adv. Funct. Mater. 24, 7645–7654 (2014).CrossRefGoogle Scholar
Yang, J., Sun, N., Huang, J., Li, Q.Q., Peng, Q., Tang, X., Dong, Y.Q., Ma, D.G., and Li, Z.: New AIEgens containing tetraphenylethene and silole moieties: Tunable intramolecular conjugation, aggregation-induced emission characteristics and good device performance. J. Mater. Chem. C 3, 2624–2634 (2015).CrossRefGoogle Scholar
Yang, Z.Y., Chi, Z.G., Yu, T., Zhang, X.Q., Chen, M.N., Xu, B.J., Liu, S.W., Zhang, Y., and Xu, J.R.: Triphenylethylene carbazole derivatives as a new class of AIE materials with strong blue light emission and high glass transition temperature. J. Mater. Chem. 19, 5541–5546 (2009).CrossRefGoogle Scholar
Li, H.Y., Chi, Z.G., Xu, B.J., Zhang, X.Q., Yang, Z.Y., Li, X.F., Liu, S.W., Zhang, Y., and Xu, J.R.: New aggregation-induced emission enhancement materials combined triarylamine and dicarbazolyl triphenylethylene moieties. J. Mater. Chem. 20, 6103–6110 (2010).CrossRefGoogle Scholar
Li, H.Y., Chi, Z.G., Zhang, X.Q., Xu, B.J., Liu, S.W., Zhang, Y., and Xu, J.R.: New thermally stable aggregation-induced emission enhancement compounds for non-doped red organic light-emitting diodes. Chem. Commun. 47, 11254–11273 (2011).CrossRefGoogle ScholarPubMed
Tang, X.Y., Yao, L., Liu, H., Shen, F.Z., Zhang, S.T., Zhang, H.H., Lu, P., and Ma, Y.G.: An efficient AIE-active blue-emitting molecule by incorporating multifunctional groups into tetraphenylsilane. Chem 20, 7589–7592 (2014).CrossRefGoogle ScholarPubMed
Shi, H.P., Xin, D.H., Gu, X.G., Zhang, P.F., Peng, H.R., Chen, S.M., Lin, G.W., Zha, Z.J., and Tang, B.Z.: The synthesis of novel AIE emitters with the triphenylethene-carbazole skeleton and para-/meta-substituted arylboron groups and their application in efficient non-doped OLEDs. J. Mater. Chem. C 4, 1228–1237 (2016).CrossRefGoogle Scholar
Dong, X.Q., Li, M., Shi, H.P., Cheng, F.Q., Roose, J., and Tang, B.Z.: Synthesis, aggregation-induced emission, and electroluminescence of a new compound based on tetraphenylethene, carbazole, and dimesitylboron moieties. Tetrahedron 72, 2213–2218 (2016).CrossRefGoogle Scholar
Shi, H.P., Zhang, X.L., Gui, C., Wang, S.J., Fang, L., Zhao, Z.J., Chen, S.M., and Tang, B.Z.: Synthesis, aggregation-induced emission and electroluminescence properties of three new phenylethylene derivatives comprising carbazole and (dimesitylboranyl)phenyl groups. J. Mater. Chem. C 5, 11741–11750 (2017).CrossRefGoogle Scholar
Dong, X.Q., Wang, S.J., Gui, C., Shi, H.P., Cheng, F.Q., and Tang, B.Z.: Synthesis, aggregation-induced emission and thermally activated delayed fluorescence properties of two new compounds based on phenylethene, carbazole and 9,9′,10,10′-tetraoxidethianthrene. Tetrahedron 74, 497–505 (2018).CrossRefGoogle Scholar
Shi, H.P., Wang, S.J., Qin, L.Y., Gui, C., Zhang, X.L., Fang, L., Chen, S.M., and Tang, B.Z.: Construction of two AIE luminogens comprised of a tetra-/tri-phenylethene core and carbazole units for non-doped organic light-emitting diodes. Dyes Pigm. 149, 323–330 (2018).CrossRefGoogle Scholar
Chen, L., Lin, G.W., Peng, H.R., Nie, H., Zhuang, Z.Y., Shen, P.C., Ding, S.Y., Huang, D.J., Hu, R.R., Chen, S.M., Huang, F., Qin, A.J., Zhao, Z.J., and Tang, B.Z.: Dimesitylboryl-functionalized tetraphenylethene derivatives: Efficient solid-state luminescent materials with enhanced electron-transporting ability for nondoped OLEDs. J. Mater. Chem. C 4, 5241–5247 (2016).CrossRefGoogle Scholar
Li, Y.H., Zhuang, Z.Y., Lin, G.W., Wang, Z.M., Shen, P.C., Xiong, Y., Wang, B.H., Chen, S.M., Zhao, Z.J., and Tang, B.Z.: A new blue AIEgen based on tetraphenylethene with multiple potential applications in fluorine ion sensors, mechanochromism, and organic light-emitting diodes. New J. Chem. 42, 4089–4094 (2018).CrossRefGoogle Scholar
Shi, H.P., Li, M., Xin, D.H., Fang, L., Roose, J., Peng, H.R., Chen, S.M., and Tang, B.Z.: Two novel phenylethene-carbazole derivatives containing dimesitylboron groups: Aggregation-induced emission and electroluminescence properties. Dyes Pigm. 128, 304–313 (2016).CrossRefGoogle Scholar
Zhang, G-F., Chen, Z-Q., Aldred, M.P., Hu, Z., Chen, T., Huang, Z., Meng, X., Zhu, M-Q.: Direct validation of the restriction of intramolecular rotation hypothesis via the synthesis of novel ortho-methyl substituted tetraphenylethenes and their application in cell imaging. Chem. Commun. 50, 12058–12060 (2014).CrossRefGoogle ScholarPubMed
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