Skip to main content
SpringerLink
Log in

Norbornene end-capped polyimide for low CTE and low residual stress with changes in the diamine linkages

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

The effects of norbornene (NE) crosslinking and diamine bridge linkages (ether, sulfone, and trifluoromethyl) on polyimide films were investigated. The purpose of this study was to study the behavior of the NE endcapped polyimide with different diamine bridge linkage structure at elevated temperatures on residual stress and modulus change. 5-Norbornene-2,3-dicarboxylic acid was introduced as the end-capping agent in order to increase the ratio of crosslinking in the structure through reverse Diels-Alder reaction. Wide angle X-ray diffraction (WAXD) was measured to study the relation of d-spacing and structure change of the bridge linkage of polymers through NE crosslinking. Coefficient of thermal expansion (CTE) and residual stress were measured to confirm the loaded stress between the substrate and polymer film through a thin film stress analyzer (TFSA). Storage (ε′) and loss modulus (ε″) were studied at elevated temperatures to study the relation of bridge linkage mobility of the polyimide at elevated temperature.

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

Similar content being viewed by others

References

  1. W. Qu, T.-M. Ko, R. H. Vora, and T.-S. Chung, Polymer, 42, 6393 (2001).

    Article  CAS  Google Scholar 

  2. M. K. Kovalev, F. Kalinina, D. A. Androsov, and C. Cho, Polymer, 54, 127 (2013).

    Article  CAS  Google Scholar 

  3. S. Y. Xiao, L. F. Che, X. X. Li, and Y. L. Wang, Microelectron. Eng., 85, 452 (2008).

    Article  CAS  Google Scholar 

  4. M. Ree, S. Swanson, and W. Volksen, Polymer, 34, 1423, (1993).

    Article  CAS  Google Scholar 

  5. T. Miwa, Y. Okabe, and M. Ishida, Polymer, 38, 4945 (1997).

    Article  CAS  Google Scholar 

  6. T. Sasaki, H. Moriuchi, S. Yano, and R. Yokota, Polymer, 46, 6968 (2005).

    Article  CAS  Google Scholar 

  7. G. Song, X. Zhang, D. Wang, X. Zhao, H. Zhou, C. Chen, and G. Dang, Polymer, 55, 3242 (2014).

    Article  CAS  Google Scholar 

  8. G. Lee, Y. Kim, and D. Kwon, Microelectron. Eng., 87, 2288 (2010).

    Article  CAS  Google Scholar 

  9. S. Numata and T. Miwa, Polymer, 30, 1170 (1989).

    Article  CAS  Google Scholar 

  10. J. Ishii, A. Takata, Y. Oami, R. Yokota, L. Vladimirov, and M. Hasegawa, Euro. Polym. J., 46, 681 (2010).

    Article  CAS  Google Scholar 

  11. J. Seo and H. Han, Polym. Degrad. Stabil., 77, 477 (2002).

    Article  CAS  Google Scholar 

  12. J. Seo, K.-Y. Cho, and H. Han, Polym. Degrad. Stabil., 74, 133 (2001).

    Article  CAS  Google Scholar 

  13. K. Kim, T. Yoo, J. Kim, H. Ha, and H. Han, J. Appl. Polym. Sci., 132, 41412 (2015).

    Google Scholar 

  14. M. Ree, T. L. Nunes, G. Czornyj, and W. Volksen, Polymer, 33, 1228 (1992).

    Article  CAS  Google Scholar 

  15. W. Jang, J. Seo, C. Lee, S.-H. Paek, and H. Han, J. Appl. Polym. Sci., 113, 976 (2009).

    Article  CAS  Google Scholar 

  16. H. Chung, J. Lee, J. Hwang, and H. Han, Polymer, 42, 7893 (2001).

    Article  CAS  Google Scholar 

  17. J.-H. Jou, P.-T. Huang, H.-C. Chen, and C.-N. Liao, Polymer, 33, 967 (1992).

    Article  CAS  Google Scholar 

  18. M. Selladurai, P. R. Sundararajan, and M. Sarojadevi, Chem. Eng. J., 203, 333 (2012).

    Article  CAS  Google Scholar 

  19. G. Socrates, Infrared and Raman Characteristics Group Frequencies, Univ. of West London, John Wiley & Sons, Chichester, 2004.

    Google Scholar 

  20. B. Laguitton, P. Mison, B. Sillion, and J. Brisson, Macromolecules, 31, 7203 (1998).

    Article  CAS  Google Scholar 

  21. M. G. Dhara and S. Banerjee, Prog. Polym. Sci., 35, 1022 (2010).

    Article  CAS  Google Scholar 

  22. X.-L. Liu, D. Wu, R. Sun, L.-M. Yu, J.-W. Jiang, and S.-R. Sheng, J. Fluor. Chem., 154, 16 (2013).

    Article  CAS  Google Scholar 

  23. V. L Rao and P. V Prabhakaran, Eur. Polym. J., 28, 363 (1992).

    Article  CAS  Google Scholar 

  24. J. Y. Do, S. K. Park, J. J. Ju, and S. Park, Opt. Mater., 26, 223 (2004).

    Article  CAS  Google Scholar 

  25. A. Nagai, A. Takahashi, M. Suzuki, and A. Mukoh, J. Appl. Polym. Sci., 44, 159 (1992).

    Article  CAS  Google Scholar 

  26. E. Khosravi, F. Iqbal, and O. M. Musa, Polymer, 52, 243 (2011).

    Article  CAS  Google Scholar 

  27. S. G. Falkovich, S. V. Lyulin, V. M. Nazarychev, S. V. Larin, A. A. Gurtovenko, N. V. Lukasheva, and A. V. Lyulin, J. Polym. Sci., Part B: Polym. Phys., 52, 640 (2014).

    Article  CAS  Google Scholar 

  28. M. Hasegawa, Y. Sakamoto, Y. Tanaka, and Y. Kobayashi, Eur. Polym. J., 46, 1510 (2010).

    Article  CAS  Google Scholar 

  29. S. Numata, K. Fujisaki, and N. Kinjo, Polymer, 28, 2282 (1987).

    Article  CAS  Google Scholar 

  30. H. Wu and L. T. Drzal, Mater. Chem. Phys., 146, 26 (2014).

    Article  CAS  Google Scholar 

  31. S. I. Kim, S. M. Pyo, and M. Ree, Macromolecules, 30, 7890 (1997).

    Article  CAS  Google Scholar 

  32. V. Carlier, J. Devaux, R. Legras, and P. T. McGrail, Macromolecules, 25, 6646 (1992).

    Article  CAS  Google Scholar 

  33. K. P. Menard, Dynamic Mechanical Analysis a Practical Introduction, CRC Press, Boca Raton, 2008.

    Book  Google Scholar 

  34. P. Lee-Sullivan and D. Dykeman, Polym. Test., 19, 155 (2000).

    Article  CAS  Google Scholar 

  35. R. Faria, J. C. Duncan, and R. G. Brereton, Polym. Test., 26, 402 (2007).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical and Biomolecular Engineering, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul, 120-749, Korea

    Taewon Yoo, Kwangin Kim & Haksoo Han

  2. Department of Chemical Engineering, School of Engineering and Applied Science, Yale University, New Haven, Connecticut, 06511, USA

    Patrick Han

  3. Department of R&D, LG Display, Gyeonggi, 413-811, Korea

    Wonbong Jang

Authors
  1. Taewon Yoo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kwangin Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Patrick Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wonbong Jang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Haksoo Han
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Haksoo Han.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yoo, T., Kim, K., Han, P. et al. Norbornene end-capped polyimide for low CTE and low residual stress with changes in the diamine linkages. Macromol. Res. 23, 776–786 (2015). https://doi.org/10.1007/s13233-015-3104-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-015-3104-3

Keywords

Search

Navigation