Material design of negative-tone polyphenol resist for EUV and EB lithography

In order to enable design of a negative-tone polyphenol resist using polarity-change reaction, five resist compounds (3M6C-MBSA-BLs) with different number of functional group of gamma-hydroxycarboxyl acid were prepared and evaluated by EB lithography. The resist using mono-protected compound (3M6C-MBSA-BL1a) showed 40-nm hp resolution at an improved dose of 52 mu C/cm(2) probably due to removal of a non-protected polyphenol while the sensitivity of the resist using a compound of protected ratio of 1.1 on average with distribution of different protected ratio was 72 mu C/cm(2). For evaluation of the di-protected compound based resist, a di-protected polyphenol. was synthesized by a newly developed synthetic route of 3-steps reaction, which is well-suited for mass production. The resist using di-protected compound (3M6C-MBSA-BL2b) also showed 40-nm hp resolution at a dose of 40 mu C/cm(2), 14 which was faster than that of mono-protected resist. Fundamental EUV lithographic evaluation of the resist using 3M6C-MI3SA-BL2b by an EUV open frame exposure tool (EUVES-7000) gave its estimated optimum sensitivity of 7 14 mJ/cm(2) and a proof of fine development behavior without any swelling.