Skip to main content
Log in

Imidazo[1,2-a]pyridine based deep-blue emitter: effect of donor on the optoelectronic properties

  • Published:
Journal of Materials Science: Materials in Electronics Aims and scope Submit manuscript

Abstract

Isomeric materials featuring triphenylamine and carbazole as a donor and 2-phenylimidazo[1,2-a]pyridine electron deficient unit as the core moiety were designed, synthesized, and studied as blue-emitting materials. As expected, their optical and electrochemical properties are prominently dependent on the nature of chromophore loading and their linking topology to the 2-phenylimidazo[1,2-a]pyridine unit. C2 substituted dyes exhibit red-shifted absorption and emission compared to their positional analogues containing donors in the C6-position of imidazopyridine. Interestingly, positive solvatochromism is exhibited by triphenylamine containing dyes, which suggests the intramolecular charge transfer from triphenylamine donor to imidazopyridine acceptor in the excited state. All the compounds revealed excellent thermal stability surpassing 355 °C. The dye possessing triphenylamine on both C2 and C6 positions of imidazopyridine showed the comparatively better electroluminescence performance in the series and achieved blue colour with CIE coordinate (0.18, 0.11).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. L. Duan, L. Hou, T.W. Lee, J. Qiao, D. Zhang, G. Dong, L. Wang, Y. Qiu, Solution processable small molecules for organic light-emitting diodes. J. Mater. Chem. 20, 6392–6407 (2010)

    Article  CAS  Google Scholar 

  2. C.W. Tang, S.A. VanSlyke, C.H. Chen, Electroluminescence of doped organic thin films. Appl. Phys. Lett. 65, 3610–3616 (1989)

    CAS  Google Scholar 

  3. J.H. Burroughes, D.D.C. Bradly, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, A.B. Holmes, Light-emitting diodes based on conjugated polymers. Nature 347, 539–541 (1990)

    Article  CAS  Google Scholar 

  4. C.W. Tang, S.A. VanSlyke, Organic electroluminescent diodes. Appl. Phys. Lett. 51, 913–915 (1987)

    Article  CAS  Google Scholar 

  5. B. Zhang, G. Tan, C.-S. Lam, B. Yao, C.-L. Ho, L. Liu, Z. Xie, W.-Y. Wong, J. Ding, L. Wang, High-efficiency single emissive layer white organic light-emitting diodes based on solution-processed dendritic host and new orange-emitting iridium complex. Adv. Mater. 24, 1873–1877 (2012)

    Article  CAS  Google Scholar 

  6. H. Liang, X. Wang, X. Zhang, Z. Ge, X. Ouyang, S. Wang, Efficient tuning of electroluminescence from sky-blue to deep-blue by changing the constitution of spirobenzofluorene derivatives. Dyes Pigments 108, 57–63 (2014)

    Article  CAS  Google Scholar 

  7. W.C. Chen, C.S. Lee, Q.X. Tong, Blue-emitting organic electro fluorescence materials: progress and prospective. J. Mater. Chem. C 3, 10957–10963 (2015)

    Article  CAS  Google Scholar 

  8. H. Ulla, M. Raveendra Kiran, B. Garudachari, M.N. Satyanarayan, G. Umesh, A.M. Isloor, Blue emitting halogen–phenoxy substituted 1,8-naphthalimides for potential organic light emitting diode applications. Opt. Mater. 37, 311–321 (2014)

    Article  CAS  Google Scholar 

  9. R. Misra, T. Jadhav, S.M. Mobin, Aryl pyrazaboles: a new class of tunable and highly fluorescent materials. Dalt. Trans. 42, 16614–16620 (2013)

    Article  CAS  Google Scholar 

  10. J. Tagare, V. Sivakumar, Recent development of phenanthroimidazole based fluorophores for blue organic light-emitting diodes (OLEDs): an overview. J. Mater. Chem. C 6, 10138–10173 (2018)

    Article  CAS  Google Scholar 

  11. M. Zhu, C. Yang, Blue fluorescent emitters: design tactics and applications in organic light-emitting diodes. Chem. Soc. Rev. 42, 4963–4976 (2013)

    Article  CAS  Google Scholar 

  12. C. Liu, Q. Fu, Y. Zou, C. Yang, D. Ma, J. Qin, Low turn-on voltage, high power efficiency, solution-processed deep-blue organic light-emitting diodes based on starburst oligofluorenes with diphenylamine end-capper to enhance the HOMO level. Chem. Mater. 26, 3074–3083 (2014)

    Article  CAS  Google Scholar 

  13. C.-J. Zheng, W.-M. Zhao, Z.-Q. Wang, D. Huang, J. Ye, X.-M. Ou, Highly efficient non-doped deep-blue organic light-emitting diodes based on anthracene derivatives. J. Mater. Chem. 20, 1560–1566 (2010)

    Article  CAS  Google Scholar 

  14. E.V. Verbitskiy, Y.A. Kvashnin, P.I. Bogdanov, M.V. Medvedeva, T.S. Svalova, A.N. Kozitsina, L.G. Samsonova, K.M. Degtyarenko, D.V. Grigoryev, A.E. Kurtcevich et al., The effect of molecular structure on the efficiency of 1,4-diazine-based D–(π)–A push-pull systems for non-doped OLED applications. Dye Pigment. 187, 109124 (2021)

    Article  CAS  Google Scholar 

  15. J. Ye, Z. Chen, M.-K. Fung, C. Zheng, X. Ou, X. Zhang, Carbazole/sulfone hybrid D-π-A-structured bipolar fluorophores for high-efficiency blue-violet electroluminescence. Chem. Mater. 25, 2630–2637 (2013)

    Article  CAS  Google Scholar 

  16. F. Khan, A. Ekbote, S.M. Mobin, R. Misra, Mechanochromism and aggregation-induced emission in phenanthroimidazole derivatives: role of positional change of different donors in a multichromophoric assembly. J. Org. Chem. 86, 1560–1574 (2021)

    Article  CAS  Google Scholar 

  17. A. Sharma, R. Balasaravanan, K.R.J. Thomas, M. Ram, D.K. DubeY, R.A.K Yadav, J.H. Jou, Tuning photophysical and electroluminescent properties of phenanthroimidazole decorated carbazoles with donor and acceptor units: beneficial role of cyano substitution. Dye Pigments 184, 108830–108842 (2021)

    Article  CAS  Google Scholar 

  18. S. Gong, Y. Chen, J. Luo, C. Yang, C. Zhong, J. Qin Bipolar tetraarylsilanes as universal hosts for blue, green, orange, and white electrophosphorescence with high efficiency and low efficiency roll-off. Adv. Funct. Mater. 21, 1168–1178 (2011)

    Article  CAS  Google Scholar 

  19. J. Huang, J.-H. Su, X. Li, M.-K. Lam, K.-M. Fung, H.-H. Fan, Bipolar anthracene derivatives containing hole- and electron-transporting moieties for highly efficient blue electroluminescence devices. J. Mater. Chem. 21, 2957–2964 (2011)

    Article  CAS  Google Scholar 

  20. W.C. Chen, Y. Yuan, S.F. Ni, Z.L. Zhu, J. Zhang, Z.Q. Jiang, L.S. Liao, F.L. Wong, C.S. Lee, Highly efficient deep-blue electroluminescence from a charge-transfer emitter with stable donor skeleton. ACS Appl. Mater. Interfaces 9, 7331–7338 (2017)

    Article  CAS  Google Scholar 

  21. L. Duan, J. Qiao, Y. Sun, Y. Qiu, Strategies to design bipolar small molecules for OLEDs: donor-acceptor structure and non-donor-acceptor structure. Adv. Mater. 23, 1137–1144 (2011)

    Article  CAS  Google Scholar 

  22. T. Youtian, W. Qiang, Y. Chuluo, Z. Cheng, Q. Jingui, M. Dongge, Multifunctional triphenylamine/oxadiazole hybrid as host and exciton-blocking material: high efficiency green phosphorescent OLEDs using easily available and common materials. Adv. Funct. Mater. 20, 2923–2929 (2010)

    Article  CAS  Google Scholar 

  23. S. Kumar, C.-C. An, S. Sahoo, R. Griniene, D. Volyniuk, J.V. Grazulevicius, S. Grigalevicius, J.-H. Jou, Solution-processable naphthalene and phenyl substituted carbazole core based hole transporting materials for efficient organic light-emitting diodes. J. Mater. Chem. C 5, 9854–9864 (2017)

    Article  CAS  Google Scholar 

  24. W. Liu, C.-J. Zheng, K. Wang, Z. Chen, D.-Y. Chen, F. Li, X.-M. Ou, Y.-P. Dong, X.-H. Zhang, Novel carbazol-pyridine-carbonitrile derivative as excellent blue thermally activated delayed fluorescence emitter for highly efficient organic light-emitting devices. ACS Appl. Mater. Interfaces 7, 18930–18936 (2015)

    Article  CAS  Google Scholar 

  25. U. Tsiko, O. Bezvikonnyi, G. Sych, R. Keruckiene, D. Volyniuk, J. Simokaitiene, I. Danyliv, Y. Danyliv, A. Bucinskas, X. Tan et al., Multifunctional Derivatives of Pyrimidine-5-Carbonitrile and Differently Substituted Carbazoles for Doping-Free Sky-Blue OLEDs and Luminescent Sensors of Oxygen. J. Adv. Res. (2021). https://doi.org/10.1016/j.dyepig.2020.109124 </bvertical-align:super;&gt

    Article  Google Scholar 

  26. Z-L. Zhu, S-F. Ni, W.-C. Chen, M. Chen, J-J. Zhu, Y. Yuan, Q-X. Tong, F-L. Wonga, C-S. Lee, Tuning electrical properties of phenanthroimidazole derivatives to construct multifunctional deep-blue electroluminescent materials. J. Mater. Chem. C 6, 3584–3591 (2018)

    Article  CAS  Google Scholar 

  27. W. Song, Y. Chen, Q. Xu, H. Mu, J. Cao, J. Huang, J. Su [1,2,4]Triazolo[1,5–a]pyridine-based host materials for green phosphorescent and delayed-fluorescence OLEDs with low efficiency roll-off. ACS Appl. Mater. Interfaces 10, 24689–24698 (2018)

  28. L-S. Cui, J. U. Kim, H. Nomura, H. Nakanotani, C. Adachi, Benzimidazobenzothiazole-based bipolar hosts to harvest nearly all of the excitons from blue delayed fluorescence and phosphorescent organic light-emitting diodes. Angew. Chem. Int. Ed. 55, 6864–6868 (2016)

    Article  CAS  Google Scholar 

  29. G.H. Lee, Y.S. Kim, Pyridine-, pyrimidine-, and triazine-based thermally activated delayed fluorescence emitters. J. Nanosci. Nanotechnol. 18, 7211–7215 (2018)

    Article  CAS  Google Scholar 

  30. S. Kothavale, K.H. Lee, J.Y. Lee, 3-Cyano imidazopyridine acceptor-based bipolar and n-type host materials for phosphorescent organic light-emitting diodes. Asian J. Org. Chem. 7, 2218–2231 (2018)

    Article  CAS  Google Scholar 

  31. Y. Yuan, J. Qiao, Y. Cao, J. Tang, M. Wang, G. Ke, Y. Lu, X. Liu, A. Lei, Exogenous-oxidant-free electrochemical oxidative C-H phosphonylation with hydrogen evolution. Chem. Commun. 55, 4230–4233 (2019).

    Article  CAS  Google Scholar 

  32. S. Jin, B. Xie, S. Lin, C. Min, R. Deng, Z. Yan, Metal-free site-specific hydroxyalkylation of imidazo[1,2-a]pyridines with alcohols through radical reaction. Org. Lett. 21, 3436–3441 (2019)

    Article  CAS  Google Scholar 

  33. A. Richaud, N. Barba-Behrens, F. Méndez, Chemical reactivity of the imidazole: a semblance of pyridine and pyrrole. Org. Lett. 13, 972–975 (2011)

    Article  CAS  Google Scholar 

  34. E.V. Verbitskiy, E.B. Gorbunov, A.A. Baranova, K. Lugovik, K.O. I, E.M. Khokhlov, G.A. Cheprakova, G.L. Kim, O.N. Rusinov, V.N. Chupakhin, Charushin, New 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives. Tetrahedron 72, 4954–4961 (2016)

    Article  CAS  Google Scholar 

  35. R. Pashazadeha, G. Sycha, S. Nasiria, K. Leitonasa, A. Lazauskasb, D. Volyniuka, P.J. Skabarac, J.V. Grazuleviciusa, Multifunctional asymmetric D-A-D’ compounds: mechanochromic luminescence, thermally activated delayed fluorescence and aggregation enhanced emission. Chem. Engine. J 401, 125962 (2020)

    Article  CAS  Google Scholar 

  36. C. Cao, W.C. Chen, S. Tian, J.-X. Chen, Z.-Y. Wang, X.-H Zheng, et al., A novel D–π–A blue fluorophore based on[1,2,4]triazolo[1,5-a]pyridine as an electron acceptor and its application in organic light-emitting diodes. Mater. Chem. Front. 3, 1071–1079 (2019)

    Article  CAS  Google Scholar 

  37. J. Zhao, B. Liu, Z. Wang, Q. Tong, X. Du, C. Zheng, H. Lin, S. Tao, X. Zhang, EQE climbing over 6% at high brightness of 14350 cd/m2 in deep-blue OLEDs based on hybridized local and charge-transfer fluorescence. ACS Appl. Mater. Interfaces 10, 9629–9640 (2018)

    Article  CAS  Google Scholar 

  38. F. Wang, J. Hu, X. Cao, T. Yang, Y. Tao, L. Mei, X. Zhang, W. Huang, A low-cost phenylbenzoimidazole containing electron transport material for efficient green phosphorescent and thermally activated delayed fluorescent OLEDs. J. Mater. Chem. C 3, 5533–5541 (2015)

    Article  CAS  Google Scholar 

  39. X. Zeng, T. Zhou, J. Liu, K. Wu, S. Li, X. Xiao, Y. Zhang, S. Gong, G. Xie, C. Yang, Incorporating thermally activated delayed fluorescence into mechanochromic luminescent emitters: high-performance solution-processed yellow organic light emitting diodes. Adv. Opt. Mater. 9, 1801071 (2018)

    Article  CAS  Google Scholar 

  40. L. Yu, Z. Wu, G. Xie, C. Zhong, Z. Zhu, H. Cong, D. Ma, C. Yang, Achieving a balance between small singlet–triplet energy splitting and high fluorescence radiative rate in a quinoxaline-based orange-red thermally activated delayed fluorescence emitter Chem. Commun. 52, 11012–11015 (2016)

    CAS  Google Scholar 

  41. D. Karthik, K.R.J. Thomas, J.H. Jou, Y.L. Chen, Synthesis, characterization and electroluminescence of carbazole-benzimidazole hybrids with thiophene/phenyl linker. Dyes Pigments 133, 132–142 (2016)

    Article  CAS  Google Scholar 

  42. S. Jeong, M.-K. Kim, S.H. Kim, J.-I. Hong, Efficient deep-blue emitters based on triphenylamine-linked benzimidazole derivatives for nondoped fluorescent organic light-emitting diodes. Org. Electron. 14, 2497–2504 (2013)

    Article  CAS  Google Scholar 

  43. W.Y. Hung, L.-C. Chi, W.-J. Chen, Y.M. Chen, S.H. Chou, K.T. Wong, A new benzimidazole/carbazole hybrid bipolar material for highly efficient deep-blue electrofluorescence, yellow–green electrophosphorescence, and two-color-based white OLEDs. J. Mater. Chem. 20, 10113–10119 (2010)

    Article  CAS  Google Scholar 

  44. S.-Y. Takizawa, J-I. Nishida, T. Tsuzuki, S. Tokito, Y. Yamashita, Phosphorescent iridium complexes based on 2-phenylimidazo[1,2-a]pyridine ligands: tuning of emission color toward the blue region and application to polymer light-emitting devices. Inorg. Chem. 46, 4308–4319 (2007)

    Article  CAS  Google Scholar 

  45. J.C. Rodríguez, R.A. Maldonado, G. Ramírez-García, E.D. Cervantes, F.N. Cruz, Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives. J. Heterocycl. Chem. 57, 2279–2287 (2020)

    Article  CAS  Google Scholar 

  46. Y. Li, J. Ding, M. Day, Y. Tao, J. Lu, M. D’iorio, Synthesis and properties of random and alternating fluorene/carbazole copolymers for use in blue light emitting devices. Chem. Mater. 16, 2165–2173 (2004)

    Article  CAS  Google Scholar 

  47. K.R.J. Thomas, J.T. Lin, Y.T. Tao, C.W. Ko, Light-emitting carbazole derivatives: potential electroluminescent materials. J. Am. Chem. Soc. 123, 9404–9411 (2001)

    Article  CAS  Google Scholar 

  48. R.K. Konidena, K.R.J. Thomas, S. Sahoo, D.K. Dubey, J.H. Jou, Multi-substituted deep-blue emitting carbazoles: comparative study on photophysical and electroluminescence characteristics. J. Mater. Chem. C 5, 709–726 (2017)

    Article  CAS  Google Scholar 

  49. G. Haberhauer, Planarized and twisted intramolecular charge transfer: a concept for fluorophores showing two independent rotations in excited state. Chem. Eur. J. 23, 9288–9296 (2017)

    Article  CAS  Google Scholar 

  50. G.A. Sherwood, R. Cheng, T.M. Smith, J.H. Werner, A.P. Shreve, L.A. Peteanu, Aggregation effects on the emission spectra and dynamics of model oligomers of MEH-PPV. J. Phys. Chem. C 113, 18851–18862 (2009)

    Article  CAS  Google Scholar 

  51. V. Joseph, K.R.J. Thomas, S. Sahoo, M. Singh, J.H. Jou, Cyano-functionalized carbazole substituted pyrene derivatives for promising organic light-emitting diodes. Dyes Pigments 158, 295–305 (2018)

    Article  CAS  Google Scholar 

  52. J. Sung, P. Kim, Y.O. Lee, J.S. Kim, D. Kim, Characterization of ultrafast intramolecular charge transfer dynamics in pyrenyl derivatives: systematic change of the number of peripheral N,N-dimethyaniline substituents. J. Phys. Chem. Lett. 2, 818–823 (2011)

    Article  CAS  Google Scholar 

  53. K. Karon, M. Lapkowski, Carbazole electrochemistry: a short review. J. Solid State Electrochem. 19, 2601–2610 (2015)

    Article  CAS  Google Scholar 

  54. A. Sharma, D. Saklani, K.R.J. Thomas Shahnawaz, S.S. Swayamprabha, J.H. Jou, Synthesis and characterization of multi-substituted carbazole derivatives exhibiting aggregation-induced emission for OLED applications. Org. Electron. 86, 105864–108842 (2020)

    Article  CAS  Google Scholar 

  55. P. Kochapradist, N. Prachumrak, R. Tarsang, T. Keawin, S. Jungsuttiwong, T. Sudyoadsuk, V. Promarak, Multi-triphenylamine-substituted carbazoles: synthesis, characterization, properties, and applications as hole-transporting materials. Tetrahedron Lett. 54, 3683–3687 (2013)

    Article  CAS  Google Scholar 

  56. I.-W. Wu, Y.-H. Chen, P.-S. Wang, C.-G. Wang, S.-H. Hsu, C.-I. Wu, Correlation of energy band alignment and turn-on voltage in organic light emitting diodes. Appl. Phys. Lett. 96, 013301 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

KRJT is thankful to SERB, New Delhi (CRG/2018/003729) and Council of Scientific and Industrial Research (CSIR), New Delhi (02(0371)/19/EMR-II) for financial support. Anupriya is grateful from Council of Scientific Industrial Research Grant Commission (CSIR), Government of India for research fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. R. Justin Thomas.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3678.6 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Anupriya, Thomas, K.R.J., Nagar, M.R. et al. Imidazo[1,2-a]pyridine based deep-blue emitter: effect of donor on the optoelectronic properties. J Mater Sci: Mater Electron 32, 26838–26850 (2021). https://doi.org/10.1007/s10854-021-07060-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10854-021-07060-5

Navigation