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Polymerization of N-(tert-butyldimethylsilyloxy)maleimide and applications of the polymers as resist materials

✍ Scribed by Sang-Tae Kim; Jin-Baek Kim; Chan-Moon Chung; Kwang-Duk Ahn


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
203 KB
Volume
66
Category
Article
ISSN
0021-8995

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✦ Synopsis


A new silicon-containing maleimide monomer, N-(tert-butyldimethylsilyloxy)maleimide (SiOMI) has been synthesized. SiOMI was radically copolymerized with styrene derivatives (XSt) to obtain alternating copolymers, P(SiOMI/XSt), in high conversions. The copolymers have high glass transition temperatures above 190ЊC, and the tert-butyldimethylsilyloxy groups are thermally stable up to 300ЊC. The SiOMI units in the copolymers were converted into N-hydroxymaleimide (HOMI) units by acidolytic deprotection of the tert-butyldimethylsilyloxy protecting groups. The facile deprotection of the side-chain tert-butyldimethylsilyloxy groups from the protected copolymers provided a significant change in solubility of the polymers due to the large polarity change. Submicron positive-tone images were obtained from the copolymers containing an onium salt as a photoacid generator by irradiation with electron beam and development with alkaline solutions. The polymer films also showed very high oxygen plasma etch resistance compared with novolac resins. The silicon-containing maleimide polymers were found to have required properties, such as good alkaline solubility after deprotection, superior adhesion, low optical density, high thermal stability with high T g , and high plasma etch resistance for applications as deep ultraviolet and electron beam resist materials.


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## Abstract __N__‐Hydroxyethylacrylamide (HEAA) was polymerized using the atom transfer radical polymerization (ATRP) with ethyl 2‐chloropropionate (ECP), copper(I) chloride (CuCl), and tris[2‐(dimethylamino)ethyl]amine (Me~6~TREN) in ethanol/water, producing poly(__N__‐hydroxyethylacrylamide) (PHE