Skip to main content
SpringerLink
Log in

Soluble Polyimides Containing Bulky Rigid Terphenyl Groups with Low Dielectric Constant and High Thermal Stability

  • Original Research Article
  • Published:
Journal of Electronic Materials Aims and scope Submit manuscript

Abstract

An aromatic diamine monomer containing an asymmetric pendant terphenyl group, 3,5-(diphenyl)phenyl-2,4-diaminobenzene, was synthesized based on a two-step reaction. The monomer was further reacted with three different commercial aromatic dianhydrides (3,3′,4,4′-biphenyltetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, 3,3′,4,4′-benzophenone tetracarboxylic dianhydride) in one-step high-temperature polycondensation to prepare a series of soluble polyimides: PI 3a–3c. The chemical structure of the obtained monomer and polymers was characterized carefully, and some selective properties were investigated in detail. These polyimides exhibit excellent thermal stability and low dielectric constant and water absorption. Their glass transition temperatures (Tg) and 10% weight loss temperatures (T10%) in N2 are up to 337°C and 596°C, respectively. Their dielectric constant and water absorption are 2.64 (at 1 MHz) and 0.73%, respectively. Moreover, the polyimides also have high optical transparency. Their values are in the range of 67–81% at a wavelength of 450 nm, and the cut-off wavelengths are in the range of 343–359 nm.

Graphic Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. W. Dong, Y. Guan, and D. Shang, RSC. Adv. 6, 21662 (2016).

    Article  CAS  Google Scholar 

  2. N. Alaslai, X. Ma, B. Ghanem, Y. Wang, F. Alghunaimi, and I. Pinnau, Macromol. Rapid Commun. 38, 1700303 (2017).

    Article  Google Scholar 

  3. C. Wang, C. Jiang, B. Yu, X. Zhao, Z. Cui, J. Li, and Q. Ren, Chin. J. Polym. Sci. 38, 759 (2020).

    Article  Google Scholar 

  4. X. Yin, Y. Feng, Q. Zhao, Y. Li, S. Li, H. Dong, W. Hu, and W. Feng, J. Mater. Chem. C 6, 6378 (2018).

    Article  CAS  Google Scholar 

  5. C. Wang, W. Chen, C. Xu, X. Zhao, and J. Li, Chin. J. Polym. Sci. 34, 1363 (2016).

    Article  CAS  Google Scholar 

  6. R. Bei, C. Qian, Y. Zhang, Z. Chi, S. Liu, X. Chen, J. Xu, and M. Aldred, J. Mater. Chem. C 5, 12807 (2017).

    Article  CAS  Google Scholar 

  7. R. Purushothaman, and H.S. Vaitinadin, J. Appl. Polym. Sci. 137, 49083 (2020).

    Article  CAS  Google Scholar 

  8. Y. Wang, J. Zhou, J. Hou, X. Chen, J. Sun, Q. Fang, and A.C.S. Appl, Polym. Mater. 1, 2099 (2019).

    CAS  Google Scholar 

  9. H. Chen, F. Dai, M. Wang, C. Chen, G. Qian, and Y. Yu, J. Polym. Sci. 59, 833 (2021).

    Article  CAS  Google Scholar 

  10. N. Mushtaq, G. Chen, L. Sidra, and X. Fang, RSC Adv. 6, 25302 (2016).

    Article  CAS  Google Scholar 

  11. L. Bai, L. Zhai, M. He, C. Wang, S. Mo, and L. Fan, React. Funct. Polym. 141, 155 (2019).

    Article  CAS  Google Scholar 

  12. Y. Liu, J. Huang, J. Tan, Y. Zeng, Q. Ding, X. Xiang, Y. Liu, and H. Zhang, J. Polym. Sci. Part A Polym. Chem. 55, 2373 (2017).

    Article  CAS  Google Scholar 

  13. C. Wang, C. Xu, Q. Li, W. Chen, and X. Zhao, Colloid. Polym. Sci. 293, 313 (2015).

    Article  CAS  Google Scholar 

  14. Y. Zhuang, R. Orita, E. Fujiwara, Y. Zhang, and S. Ando, Macromolecules 52, 3813 (2019).

    Article  CAS  Google Scholar 

  15. C. Wang, S. Cao, W. Chen, X. Zhao, J. Li, and Q. Ren, RSC Adv. 7, 26420 (2017).

    Article  CAS  Google Scholar 

  16. X. Wu, C. Shu, X. He, S. Wang, X. Fan, Z. Yu, D. Yan, and W. Huang, Macromol. Chem. Phys. 221, 1900506 (2020).

    Article  CAS  Google Scholar 

  17. A. Alghannam, G. Yahaya, A. Hayek, I. Mokhtari, Q. Saleem, D. Sewdan, and A. Bahamdan, J. Membr. Sci. 553, 32 (2018).

    Article  CAS  Google Scholar 

  18. S. Hsiao, W. Liao, and G. Liou, Polymers 9, 511 (2017).

    Article  Google Scholar 

  19. C. Terraza, L. Tagle, J. Santiago-García, R. Canto-Acosta, M. Aguilar-Vega, R. Hauyon, D. Coll, P. Ortiz, G. Perez, L. Herrán, B. Comesaña-Gándara, N. McKeown, and A. Tundidor-Camba, Polymer 137, 283 (2018).

    Article  CAS  Google Scholar 

  20. C. Zhang, P. Li, and B. Cao, J. Membr. Sci. 530, 176 (2017).

    Article  CAS  Google Scholar 

  21. C. Wang, X. Zhao, and G. Li, Chin. J. Chem. 30, 2466 (2012).

    Article  CAS  Google Scholar 

  22. H. Lao, N. Mushtaq, G. Chen, H. Jiang, Y. Jiao, A. Zhang, and X. Fang, Polymer 206, 122889 (2020).

    Article  CAS  Google Scholar 

  23. L. Li, Y. Xu, J. Che, and Z. Ye, Polym. Adv. Technol. 30, 120 (2019).

    Article  CAS  Google Scholar 

  24. L. Yi, W. Huang, and D. Yan, J. Polym. Sci. Part A Polym. Chem. 55, 533 (2017).

    Article  CAS  Google Scholar 

  25. Y. Liu, L. Tang, L. Qu, S. Liu, Z. Chi, Y. Zhang, and J. Xu, Chin. J. Polym. Sci. 37, 416 (2019).

    Article  CAS  Google Scholar 

  26. Y. Zhuang, J. Seong, Y. Do, W. Lee, M. Lee, M. Guiver, and Y. Lee, J. Membr. Sci. 504, 55 (2016).

    Article  CAS  Google Scholar 

  27. C. Jiang, C. Wang, B. Yu, X. Zhao, J. Li, and Q. Ren, J. Macromol. Sci. Part A 58, 44 (2020).

    Article  Google Scholar 

  28. T. Li, H. Huang, L. Wang, and Y. Chen, RSC Adv. 7, 40996 (2017).

    Article  CAS  Google Scholar 

  29. M. Hasegawa, Polymers 9, 520 (2017).

    Article  Google Scholar 

  30. P. Wen, R. He, X. Li, and M. Lee, Polymer 117, 76 (2017).

    Article  CAS  Google Scholar 

  31. C. Yi, W. Li, S. Shi, K. He, P. Ma, M. Chen, and C. Yang, Sol. Energy 195, 340 (2020).

    Article  CAS  Google Scholar 

  32. S. Bong, H. Yeo, B. Ku, M. Goh, and N. You, Macromol. Res. 26, 85 (2018).

    Article  CAS  Google Scholar 

  33. S. Hsiao, and Y. Chou, Macromol. Chem. Phys. 215, 958 (2014).

    Article  CAS  Google Scholar 

  34. N. Belov, R. Chatterjee, R. Nikiforov, V. Ryzhikh, S. Bisoi, A. Kumar, S. Banerjee, and Y. Yampolskii, Sep. Purif. Technol. 217, 183 (2019).

    Article  CAS  Google Scholar 

  35. C. Wang, W. Chen, Y. Chen, X. Zhao, J. Li, and Q. Ren, Mater. Chem. Phys. 143, 773 (2014).

    Article  CAS  Google Scholar 

  36. A. Tamboli, and N. Maldar, J. Polym. Res. 26, 139 (2019).

    Article  Google Scholar 

  37. S. Hsiao, and C. Wu, Polym. Int. 66, 916 (2017).

    Article  CAS  Google Scholar 

  38. C. Wang, W. Chen, Y. Chen, X. Zhao, J. Li, and Q. Ren, Mater. Chem. Phys. 144, 553 (2014).

    Article  CAS  Google Scholar 

  39. C. Wang, B. Yu, C. Jiang, X. Zhao, J. Li, and Q. Ren, Polym. Bull. 77, 6509 (2020).

    Article  CAS  Google Scholar 

  40. S. Banerjee, M. Madhra, and V. Kute, J. Appl. Polym. Sci. 93, 821 (2004).

    Article  CAS  Google Scholar 

  41. B. Deng, S. Zhang, C. Liu, W. Li, X. Zhang, H. Wei, and C. Gong, RSC Adv. 8, 194 (2018).

    Article  CAS  Google Scholar 

  42. Q. Wu, X. Ma, F. Zheng, X. Lu, and Q. Lu, Eur. Polym. J. 120, 109235 (2019).

    Article  CAS  Google Scholar 

  43. S. Huang, X. Liu, M. Wei, Z. Huang, and S. Sheng, High Perform. Polym. 30, 500 (2017).

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the Key Research Project of Jiangsu Province (BE2017645), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and the Postgraduate Research & Practice Innovation Program of Jiangsu Province (SJCX21_1184).

Author information

Authors and Affiliations

  1. Jiangsu Key Laboratory of Environmentally Friendly Polymeric Materials, School of Materials Science and Engineering, Changzhou University, Changzhou, 213164, China

    Hui Zheng, Chenyi Wang, Zhengwang Tao, Cairong Jiang, Xiaoyan Zhao, Jian Li & Qiang Ren

Authors
  1. Hui Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chenyi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhengwang Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Cairong Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiaoyan Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jian Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Qiang Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chenyi Wang.

Ethics declarations

Conflict of interest

The authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zheng, H., Wang, C., Tao, Z. et al. Soluble Polyimides Containing Bulky Rigid Terphenyl Groups with Low Dielectric Constant and High Thermal Stability. J. Electron. Mater. 50, 6981–6990 (2021). https://doi.org/10.1007/s11664-021-09192-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11664-021-09192-0

Keywords

Search

Navigation