Characterization and Lithographic Application of Calix[4]resorcinarene Derivatives

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• 作者：Hiroshi Ito ; Tomonari Nakayama ; Mark Sherwood ; Dolores Miller ; Mitsuru Ueda
• 刊名：Chemistry of Materials
• 出版年：2008
• 出版时间：January 8, 2008
• 年：2008
• 卷：20
• 期：1
• 页码：341 - 356
• 全文大小：1441K
• 年卷期：v.20,no.1(January 8, 2008)
• ISSN：1520-5002

文摘

Calix[4]resorcinarenes were prepared by the condensation of resorcinol and aldehydes (acetaldehyde, benzaldehyde, and 4-isopropylbenzaldehyde), and two isomers, C_4v (ccc) and C_2v (ctt), were separated by fractional crystallization. The products were characterized by NMR and FTIR, and their dissolution rate in aqueous base was measured. The eight hydroxyl groups of the calix[4]resorcinarenes were protected with acid labile t-butoxycarbonyl and t-butoxycarbonylmethyl. The protected calixarenes were thoroughly characterized by differential scanning calorimetry, FTIR, and variable-temperature ¹H and ¹³C NMR. Their interaction with 4-isopropylphenol through hydrogen bonding was investigated by ¹³C NMR and correlated with their inhibition effect of dissolution of poly(4-hydroxystyrene-co-t-butyl acrylate) in an aqueous base, as studied by quartz crystal microbalance. Finally, the protected calixarenes were employed as a dissolution inhibitor of polyhydroxystyrene-based deep UV and electron beam chemical amplification resists to improve their contrast and performance.