High-performance intrinsic low-k polymer via the synergistic effect of its three units: adamantyl, perfluorocyclobutylidene and benzocyclobutene

Abstract

Intrinsic highly cross-linked low-k benzocyclobutene polymer functionalized with adamantyl and perfluorocyclobutylidene.

Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

“…Over the past decades, many researchers around the world have been focused on the preparation of PFCB polymers [ 27 , 31 , 32 , 33 , 44 , 45 , 46 , 47 , 48 , 49 , 60 , 61 , 62 , 63 , 64 ]. Monomers containing TFVE moieties have been developed and used to obtain PFCB polymers [ 31 , 60 , 61 , 62 ]. PFCB precursors bearing organic-inorganic cores including siloxanes and polyhedral oligomeric silsesquioxanes (POSS) have also been reported [ 28 , 65 , 66 ].…”

“…PFCB polymers with low dielectric constants (D k ) and low dissipation factors (D f ) have attracted much attention because of their potential use in the manufacture of high-performance electronic devices [ 28 , 29 , 30 , 31 , 33 , 68 ]. Although there are different ways of lowering the D k and D f values of polymeric materials, two of the most common techniques are (1) introducing less polarizable groups (e.g., C−H, C−C, C−Si, C−O, and C−F bonds) into the polymer backbone and (2) decreasing the material density by increasing the porosity [ 30 , 31 , 32 ]. Luo et al [ 30 ] synthesized a new microporous PFCB aryl ether polymer from a tetrahedral structured monomer containing thermo-polymerizable TFVEs with −CF 2 H terminal groups ( Scheme 4 ).…”

“…Kong et al [ 31 ] also synthesized a crosslinked PFCB polymer (structure shown in Figure 1 a) from a monomer obtained by combining rigid adamantyl, PFCB, and benzocyclobutene groups. The introduction of PFCB can modify the polarizability and surface energy of the polymer, while the presence of rigid adamantyl groups can affect the free volume and density of the resulting material.…”

“…The versatility of the aryl ether linkages, presence of thermally stable aromatic rings, and improved processability due to the PFCB ring make the utility of PFCB polymers promising in many practical applications [ 9 , 11 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ]. This section summarizes several important uses of PFCBs, such as high-performance protective coatings, membrane layers, dielectrics, and optical materials.…”

“…They are generally prepared by free radical mediated [2 + 2] thermal cyclopolymerization of functional aryl trifluorovinyl ether (TFVE) monomers at temperatures above 150 °C without using any catalysts or initiators ( Scheme 1 a) [ 12 , 18 , 19 ]. The cycloaddition of the fluoroolefins produces fluorinated cyclobutane rings, giving an overall amorphous PFCB polyaryl ethers with good solubility and solution processability for an array of new applications [ 9 , 11 , 12 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ]. In the past decades, our group has been dedicated to the synthesis and applications of tailored PFCB polymers [ 12 , 20 , 44 , 45 , 46 , 47 , 48 , 49 ].…”