Photopatterning of Low Dielectric Constant Cycloolefin Polymers Using Azides and Diazirines

Abstract

Polymers are widely used as insulators in electronic devices. Low dielectric constant polymers are desirable since this lowers the potential for unintentional crosstalk and inductive coupling between conductors. Attempts to photopattern a low dielectric constant polymer, poly(5-hexyl-2-norbornene) (poly(1)), with a bis(azide) were unsuccessful. Incorporation of butenyl pendent groups improved patterning, but the dielectric constant of the cross-linked film was relatively high (2.60). A difunctional bis(diazirine) (compound 4) was synthesized and characterized by NMR and MS. Compound 4 rendered unreactive, aliphatic cycloolefin polymers such as poly(1) photopatternable, yielding negative tone patterns with good resolution. The dielectric constant of films cross-linked with compound 4 was substantially lower than the films cross-linked with bis(azide) (2.09 for poly(1)).

Structure–function relationships in aryl diazirines reveal optimal design features to maximize C–H insertion

“…1,2 The ability to rapidly and controllably generate carbenes from stable and readily accessed precursor molecules allows one to label (or 'tag') binding partners, 3 isolate reaction products, 4 or crosslink polymer materials. [5][6][7] In recent years, diazirine motifs have enjoyed enormous popularity as carbene precursors, for applications ranging from biological target identification through to adhesion of commodity plastics (Fig. 1).…”

Photoresponsive Polymers with Aggregation-Induced Emission

“…Photopatterning is a process in which the pattern on the template is transferred to the materials through a photochemical reaction. It plays an irreplaceable role in optoelectronics and has attracted a lot of attention for its significant accuracy compared to molding and printing. − Photopatterning not only greatly improves the precision of material surface modification but also extends the application of polymer materials to highly precise field-effect transistors, high-resolved flexible display devices, and highly sensitive wearable detection devices.…”

Cure kinetics and properties of high-performance epoxy thermosets cured with active ester-terminated poly (aryl ether ketone)

“…Thus, lower D k and D f polymeric materials are found to dominate the high-frequency packaging section of electronics. Although the dielectric properties of epoxy resins are not as good as those of polyimides, 48 cycloolefin polymers, 49 liquid crystal polyester, 50 it is still one of the attractive polymeric materials due to its relatively low price. The dielectric properties of all these epoxy thermosets were listed in Table 4.…”