Citation: Bao, F.; Liu, Y.; Shi, L.; Cui,
J.; Ji, M.; Liu, H.; Yu, J.; Zhu, C.; Xu, J.
Non-Coplanar Diphenyl Fluorene
and Weakly Polarized Cyclohexyl
Can Effectively Improve the
Solubility and Reduce the Dielectric
Constant of Poly (Aryl Ether Ketone)
Resin. Polymers 2023, 15, 962.
https://doi.org/10.3390/
polym15040962
Academic Editors: Zhikang Yuan,
Sichen Qin and Geng Chen
Received: 29 December 2022
Revised: 7 February 2023
Accepted: 9 February 2023
Published: 15 February 2023
Copyright: © 2023 by the authors.
Licensee MDPI, Basel, Switzerland.
This article is an open access article
distributed under the terms and
conditions of the Creative Commons
Attribution (CC BY) license (https://
creativecommons.org/licenses/by/
4.0/).
polymers
Article
Non-Coplanar Diphenyl Fluorene and Weakly Polarized
Cyclohexyl Can Effectively Improve the Solubility and Reduce
the Dielectric Constant of Poly (Aryl Ether Ketone) Resin
Feng Bao
1,
*
,†
, Yanxing Liu
1,†
, Ludi Shi
2
, Jinze Cui
1
, Muwei Ji
3
, Huichao Liu
1
, Jiali Yu
1
, Caizhen Zhu
1,
*
and Jian Xu
1
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
Department of Chemistry, College of Science, Shantou University, Shantou 515063, China
* Correspondence: bfisvip@163.com (F.B.); czzhu@szu.edu.cn (C.Z.)
† These authors contributed equally to this work.
Abstract: With the rapid development of high-frequency communication and large-scale integrated
circuits, insulating dielectric materials require a low dielectric constant and dielectric loss. Poly (aryl
ether ketone) resins (PAEK) have garnered considerable attention as an intriguing class of engineering
thermoplastics possessing excellent chemical and thermal properties. However, the high permittivity
of PAEK becomes an obstacle to its application in the field of high-frequency communication and
large-scale integrated circuits. Therefore, reducing the dielectric constant and dielectric loss of PAEK
while maintaining its excellent performance is critical to expanding the PAEK applications mentioned
above. This study synthesized a series of poly (aryl ether ketone) resins that are low dielectric,
highly thermally resistant, and soluble, containing cyclohexyl and diphenyl fluorene. The effects
of cyclohexyl contents on the properties of a PAEK resin were studied systematically. The results
showed that weakly-polarized cyclohexyl could reduce the molecular polarization of PAEK, resulting
in low permittivity and high transmittance. The permittivity of PAEK is 2.95–3.06@10GHz, and
the transmittance is 65–85%. In addition, the resin has excellent solubility and can be dissolved in
NMP, DMF, DMAc, and other solvents at room temperature. Furthermore, cyclohexyl provided
PAEK with excellent thermal properties, including a glass transition temperature of 239–245
◦
C and
a 5% thermogravimetric temperature, under a nitrogen atmosphere of 469–534
◦
C. This makes it a
promising candidate for use in high-frequency communications and large-scale integrated circuits.
Keywords: poly (aryl ether ketone); permittivity; solubility; cyclohexyl; diphenyl fluorene
1. Introduction
The rapid development of high-frequency communication and large-scale integrated
circuits has raised new requirements for interlayer insulating dielectric materials [1–3].
Insulating dielectric materials are required to have a low dielectric constant and low
dielectric loss under high frequency, as well as excellent thermal and mechanical properties,
processability, dimensional stability, and low water absorption [4–6].
Traditional general polymeric materials, such as polyethylene (PE), polypropylene
(PP), etc., have low permittivity and dielectric loss but fail to meet requirements due
to application–temperature mismatch. Numerous special engineering plastics, such as
traditional polyimide (PI) and liquid crystal polymer (LCP), were expected to meet re-
quirements due to their superior thermal and mechanical performance and dielectric
properties [7,8]. However, the dielectric constant (D
k
) of 3.0–3.5 is insufficient for appli-
cation in high-frequency communication and large-scale integrated circuits. Based on
the Clausius–Mossotti equation, low-dielectric materials can be prepared by reducing
Polymers 2023, 15, 962. https://doi.org/10.3390/polym15040962 https://www.mdpi.com/journal/polymers