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Highly Heat-Resistant Materials for Microelectronics: Hydrodynamic, Optical, and Conformational Properties of Fluorine Containing Poly(Amido-ortho-Hydroxy Amide)

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Abstract

The polycondensation of the mixture of diamines 5,5-methylene bis(2-aminophenol) and 4,4-(hexafluoroisopropylidene)dianiline (molar ratio 0.8:0.2) with isophthaloyl dichloride was used to synthesize poly(amido-o-hydroxy amide) (POA-F) - new heat resistant binder of the composites for microelectronics. The copolymer was fractionated, its hydrodynamic, optical, and conformational properties were researched, and molecular masses (ММ) of the fractions were defined. The polydispersity index was estimated. Based on experimental data, calculation of the size of a segment of Kuhn characterizing degree of an intramolecular orientation order and value of coefficients of the equation of Mark-Kuhn-Hauvink for viscometric and diffusion data were performed. It was demonstrated that introducing 20 mol % of the monomer with -CF3-groups does not lead to any changes in conformational properties of the macromolecules and does not change the degree of intramolecular orientational order (the Kuhn segment length). Optical characteristics of POA-F solutions are virtually similar to the corresponding values for POA prepared with the use of single amine-containing component-5,5-methylene bis(2-aminophenol). The received MM distribution for POA-F (prepolymer) provided the solubility of its films in alkaline solutions. The heat resistance (τ5 and τ10-temperatures corresponding to 5% and of 10% PBO-F mass loss of a polymer) of the powders and the films of PBO, PBO-F were determined. The electrophysical parameters-dielectric permittivity (ε) and dielectric loss tangent (tan δ) of the PBO-F films decreased down to 3.30 and 0.017, in comparison 3.40 and 0.025 for PBO respectively.

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References

  1. Hsiao Sh-H, Dai L-R. Synthesis and Properties of Novel Aromatic poly(o-hydroxyamide)s and Polybenzoxazoles Based on the Bis(Either benzoyl Chloride)s from Hydroquinone and Its Methyl-, Tert-butyl-, and Phenyl-substituted Derivatives [J]. J. Polymer Sci. Part A Polymer Chem., 1999, 37: 2 129–2 136

    Article  CAS  Google Scholar 

  2. Cuadrado BD, Fernández AM, José G, et al. A Thermally Rearranged Polybenzoxazoles Made from Poly (ortho -hydroxyamide)s. Character-Ization and Evaluation as Gas Separation Membranes [J]. Reactive and Functional Polymers, 2018, 127: 38–47

    Article  Google Scholar 

  3. Mukhin N, Afanasjev V, Sokolova I, et al. Heat-resistant Ferroelectric- polymer Nanocomposite with High Dielectric Constant [J]. Materials, 2018, 11: 1 439–1 447. https://doi.org/10.3390/ma11081439

    Article  Google Scholar 

  4. Lebedeva GK, Bazhenova AS, Rudaya LI, et al. Highly Heat-resistant poly(o-hydroxy amides) Binders of Polyfunctional Composites for Microelectronics [J]. Rus. J. of Appl. Chemistry, 2016, 89: 1 647–1 654

    Article  CAS  Google Scholar 

  5. Rudaja L, Shamanin V, Lebedeva C, et al. The Method of Producing of Heatresistant Positive Photoresists [P]v. Russian Federation Patent 2379731, 2010-01-20

    Google Scholar 

  6. Rudaya L, Shamanin V, Nasledov D, et al. Heat-resistant Photoresists [P]. Russian Federation Patent 2549532, 2015-04-27

    Google Scholar 

  7. Andreeva LN, Strelina IA, Okatova OV, et al. Hydrodynamic and Conformational Characteristics Poly(ortho-Hydroxy Amide) [J]. Rus. Izv. Sankt-Petersburg Gos. Tekhnol. Institute (Tekh. Univ,), 2013, 22: 33–36

    Google Scholar 

  8. Rudaya LI, Strelina IA, Okatova OV, et al. Highly Thermally Stable Polyfunctional Materials for Microelectronics: Hydrodynamic, Optical, and Conformational Properties of Si-containing Poly(ortho-Hydroxy Amide) [J]. Rus. J. Appl. Chem., 2017, 90: 1 771–1 777

    Article  CAS  Google Scholar 

  9. Tao L, Yang H, Liu J, et al. Synthesis of Fluorinated Polybenzoxazoles with Low Dielectric Constants [J]. J. Pol. Sci. Part A Polymer Chemistry, 2010, 48: 4 668–4 680

    Article  CAS  Google Scholar 

  10. Banerjee S. Handbook of Specialty Fluorinated Polymers Preparation, Properties, and Applications [M]. Oxford: Elsevier, 2015

    Google Scholar 

  11. Tsvetkov NV. Rigid Chain Polymers [M]. New York: Plenum Press, 1989

    Google Scholar 

  12. Tsvetkov VN, Andreeva LN. Flow and Electric Birefringence in Rigid- Chain Polymer Solutions [J]. Adv. Pol. Sci., 1981, 39: 95–207

    Article  CAS  Google Scholar 

  13. Tsvetkov NV, Pogodina NV, Startchenko LI, et al. Flow Birefringence and Equilibrium Rigidity of Molecules of Para- and Meta- aromatic Polyamides Copolymers [J]. Pol. Sci. of USSR, 1981, 23A6(12): 2 681–2 690

    Google Scholar 

  14. Tsvetkov VN, Andreeva LN, Tsvetkov NV. Anisotropy of Segments and Monomer Units of Polymer Molecules. In: Brandup J, Immergut EH, Grulke EA (eds) Polymer Handbook 4th edn [M]. New York: Willey and Sons, 1999

    Google Scholar 

  15. Vereschagin AN. Polarizability of Molecules [M]. Moscow: Nauka, 1980

    Google Scholar 

Download references

Acknowledgments

The authors are grateful to senior researcher Dr. L.N. Andreeva for assistance in experimental work, interpretation of the results, valuable comments and discussion during the preparation of the manuscript.

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Correspondence to Stanislav M Ramsh.

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Funded by the Ministry of Education and Science of the Russian Federation (No.10.7608.2017/8.9)

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Strelina, I.A., Rudaya, L.I., Okatova, O.V. et al. Highly Heat-Resistant Materials for Microelectronics: Hydrodynamic, Optical, and Conformational Properties of Fluorine Containing Poly(Amido-ortho-Hydroxy Amide). J. Wuhan Univ. Technol.-Mat. Sci. Edit. 35, 223–230 (2020). https://doi.org/10.1007/s11595-020-2247-z

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  • DOI: https://doi.org/10.1007/s11595-020-2247-z

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