Synthesis of Hyperbranched Polyacetals containing C-(4-t-butylbenz)calix[4]resorcinarene; Resist Properties for Extreme Ultraviolet (EUV) Lithography

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We synthesized the various hyperbranched polyacetals poly(t-BCRA[4]-co-BVOC), poly(t-BCRA[4]-co-BVOP), poly(t-BCRA[4]-co-BVOXP), poly(t-BCRA[4]-co-BVBC), and poly(t-BCRA[4]-co-TVCH) by polyaddition of C-(4-t-butylbenz)calix[4]resorcinarene (t-BCRA[4]) with 1,4-bis(4-vinyloxy)cyclohexane (BVOC), 1,3-bis(vinyloxy)propane (BVOP), 1,5-bis(vinyloxy)-3-oxapentane (BVOXP), 4,4'-bis(vinyloxy)-1,1'-bicyclohexane (BVBC), and 1,3,5-tris(vinyloxy)cyclohexane (TVCH), respectively. The resist sensitivity of the synthesized polymers using EUV exposure tool was consistent with their structures, and is in the order poly(t-BCRA[4]-co-BVOC) > poly(t-BCRA[4]-co-BVOXP) > poly(t-BCRA[4]-co-TVCH) > poly(t-BCRA[4]-co-BVOP) >> poly(t-BCRA[4]-co-BVBC). Furthermore, poly(t-BCRA[4]-co-BVOC) showed good resist properties such as out-gassing property using EUV exposure tool, film-thickness loss property, and etching durability. Overall, our results indicate that hyperbranched polyacetal poly(t-BCRA[4]-co-BVOC) has high potential as next-generation resist material for EUV photolithography.

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