Negative-Working Photosensitive Poly(phenylene ether) Based on Poly(2,6-dimethyl-1,4-phenylene ether), a Cross-Linker, and a Photoacid Generator

Abstract

A novel benzyl cation type cross-linker, hex-1,6-ylenebis[oxy(2,4,6-tris(acetyloxymethyl)-3,5-dimethylbenzene)] (HOAD), that suppresses acid-catalyzed self-polycondensation has been developed. Furthermore, a negative-working, photosensitive poly(phenylene ether) (PSPPE) based on poly(2,6-dimethyl-1,4-phenylene ether) (PPE), HOAD, and diphenylidonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS) as a photoacid generator (PAG) has been developed. This resist system does not contain a high thermal curing process. The resist consisting of PPE (83 wt %), HOAD (10 wt %), and DIAS (7 wt %) showed excellent sensitivity (D 0.5) of 43 mJ/cm2 and high contrast (γ0.5) of 11 when it was exposed to 365 nm wavelength UV light (i-line), postexposure baked (PEB) at 190 °C for 5 min, and developed by dipping in toluene at 25 °C. A fine negative-type pattern having 6 μm resolution on 2.4 μm thick film on a silicon wafer was obtained by exposure to 300 mJ/cm2 of the i-line by using a contact-printed mode. The resulting PSPPE film, cured at 220 °C for 1 h under nitrogen, had a low dielectric constant (ε: 2.61), good thermal stability, and low water absorption.

Synthesis and properties of oxetane‐based polysiloxanes used for cationic UV curing coatings

“…The UV curing technology has been widely used in various industrial fields due to its crucial advantages including rapid cure, reduced pollution, low energy consumption, easy finishing, and superior product quality 1–5. Although this technology has been well‐accepted for several decades, the developments of novel monomers and oligomers with special performance are still active to meet the demands from markets and applications 6–10. One of the most important and attractive subjects is UV curable siloxane‐containing monomers and oligomers, due to the excellent properties such as flexibility, hydrophobicity, weatherability, chemical resistance, release performance, and thermal stability 11–14.…”

Synthesis and characterization of polymer electrolytes based on cross‐linked phenoxy‐containing polyphosphazenes

“…In this work, we prepared cross‐linked polyphosphazene in two steps: first, the synthesis of phenoxy‐containing polyphosphazene (MEEPP) by the reaction of poly(dichlorophosphazene) with diethylene glycol monomethyl ether and 2‐phenoxyethanol; and the second, reaction of the resulting phenoxy‐containing polyphosphazene with 2,4,6‐tris[bis(methoxymethyl)amino]‐1,3,5‐triazine (CYMEL) as a cross‐linking agent. CYMEL is widely used with epoxy, polyester, acrylic and alkyl resins and provides the desired balance of flexibility, exterior durability, chemical resistance and film toughness . This method provides a simple and efficient way to produce an electrolyte thin film by solution casting.…”

“…CYMEL is widely used with epoxy, polyester, acrylic and alkyl resins and provides the desired balance of flexibility, exterior durability, chemical resistance and film toughness. [25][26][27][28] This method provides a simple and efficient way to produce an electrolyte thin film by solution casting. Accordingly, we investigated the conductivity and electrochemical behavior of polymer electrolyte membranes by varying cross-linking extent of phenoxy-containing polyphosphazenes.…”