Non-chemically Amplified Negative Molecular Resist Materials using Polarity Change by EUV Exposure

Abstract

We examined the synthesis, physical properties, and resist property of the molecular non-chemically amplified resist materials. By the condensation reaction of tri(4-hydroxyphenyl)methane (HPM) and various bisphenols (BisA, BisAF, HPE, and TDP) with 4-bromoethoxyphenyl methyl sulfide (BEPMS), the compounds (HPM-BEPMS, BisA-BEPMS, BisAF-BEPMS, HPE-BEPMS, and TDP-BEPMS) containing sulfide moieties were synthesized. These were reacted with silver trifluoromethanesulfonate and iodomethane, yielding corresponding compounds HPM-BEPMS_ion, BisA-BEPMS_ion, BisAF-BEPMS_ion, HPE-BEPMS_ion, and TDP-BEPMS_ion, respectively. They have good physical properties (solubility, film-forming ability, and thermal stability) and high nega-type resist sensitivity in an extreme ultraviolet (EUV) exposure tool, indicating these were good candidate to offer higher resolution resist pattern.