Synthesis and property of noria (water-wheel like macrocycle) derivatives with pendant alkoxyl and adamantyl ester groups, and their application for extreme ultraviolet resist

被引:22
作者
Niina, Nobumitsu [1 ]
Kudo, Hiroto [2 ]
Oizumi, Hiroaki [3 ]
Itani, Toshiro [3 ]
Nishikubo, Tadatomi [4 ]
机构
[1] Kanagawa Univ, Grad Sch Engn, Dept Appl Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan
[2] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Suita, Osaka 5648680, Japan
[3] Selete Semicond Leading Edge Technol Inc, Res Dept 3, Tsukuba, Ibaraki 3058569, Japan
[4] Kanagawa Univ, Fac Engn, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan
关键词
Synthesis; Cyclic oligomer; Resist; Noria; Extreme ultraviolet; Dynamic covalent chemistry; Photo-acid generator; CALIXARENE NEGATIVE RESIST; MOLECULAR GLASS RESISTS; ELECTRON-BEAM RESIST; HIGH-RESOLUTION; LITHOGRAPHY;
D O I
10.1016/j.tsf.2013.02.016
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Noria derivatives with pendant methoxy and adamantyl ester moieties (noria(MP)-AD(n)) were synthesized by the substitution reaction of noria analogues with 12 methoxy groups (noria(MP)) and 2-bromoacetyloxy-2-methyladamantane (BMA), and their degrees of introduction of adamantyl ester moieties (DI) could be controlled by the feed ratios of noria(MP) and BMA. The physical properties such as solubility, film-forming ability, and thermal stability of noriaMP-AD(n) were also examined to assess the suitability for application as extreme ultraviolet (EUV)-resist materials. The patterning property of noria(MP)-AD(18) (DI= 18) and noria(MP)-AD(54) (DI= 54) was investigated in an EUV-resist system, and noria(MP)-AD(18) yielded higher resolution than noriaMP-AD54, providing a clear line and space pattern with a resolution of 32 nm and a line-width roughness of 10.5 nm by exposure dose of 9.0 mJ/cm(2). (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:459 / 464
页数:6
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