Design and Synthesis of Low Dielectric Poly(aryl ether ketone) from Incorporation Bulky Fluorene Groups and Regular Hydroquinone Structure

Ludi Shi; Feng Bao; Yanxing Liu; Hong Li; Tang Zhu; Huichao Liu; Jiali Yu; Yongna Qiao; Caizhen Zhu; Jian Xu

doi:10.1021/acs.langmuir.3c01307

Design and Synthesis of Low Dielectric Poly(aryl ether ketone) from Incorporation Bulky Fluorene Groups and Regular Hydroquinone Structure

Langmuir. 2023 Aug 15;39(32):11439-11447. doi: 10.1021/acs.langmuir.3c01307. Epub 2023 Jul 31.

Authors

Ludi Shi^{1

2

3}, Feng Bao¹, Yanxing Liu¹, Hong Li¹, Tang Zhu¹, Huichao Liu¹, Jiali Yu¹, Yongna Qiao¹, Caizhen Zhu¹, Jian Xu¹

Affiliations

¹ Institute of Low-Dimensional Materials Genome Initiative, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen, 518060, China.
² Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
³ University of Chinese Academy of Sciences, Beijing, 100049, China.

PMID: 37524048
DOI: 10.1021/acs.langmuir.3c01307

Abstract

To decrease the dipole polarization rate and reduce the dielectric constant of poly(aryl ether ketone) (PAEK) resin, 1,4-di(4-fluorobenzoyl) cyclohexane (DFBCH), a weakly polarizing cyclohexane-based monomer, was designed and synthesized as the primary reactant. The bulky fluorene group was incorporated to increase the free volume of the resin, further reducing the dielectric constant. Additionally, hydroquinone with a symmetric and regular structure was utilized to enhance the molecular chain's regularity and reduce dipole relaxation, further lowering the resin's dielectric constant and dielectric loss. The PFQEKs series resins exhibited excellent thermal stability with glass transition temperature (T_g) ranging from 222 to 239 °C and 5% weight loss (T_d5%) ranging from 458 to 463 °C, with different monomer ratios. As the hydroquinone content increased, the dielectric constant (D_k) and dielectric loss (D_f) of the resin decreased significantly, with D_k ranging from 2.92 to 2.77 and D_f ranging from 0.011 to 0.008 at 10 GHz.