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    High molecular weight silicone compounds, resist compositions, and patterning method
    1.
    发明授权
    High molecular weight silicone compounds, resist compositions, and patterning method 有权
    高分子量硅氧烷化合物，抗蚀剂组合物和图案化方法

    公开(公告)号：US06730453B2

    公开(公告)日：2004-05-04

    申请号：US09887320

    申请日：2001-06-25

    申请人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

    发明人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

    IPC分类号： G03F7075

    CPC分类号： G03F7/0045 ,  C08G77/14 ,  C08G77/38 ,  C08G77/388 ,  C08G77/50 ,  G03F7/0392 ,  G03F7/0757

    摘要： The invention provides a high molecular weight silicone compound comprising recurring units of formula (1) and having a weight average molecular weight of 1,000-50,000. Some or all of the hydrogen atoms of carboxyl groups or carboxyl and hydroxyl groups in the silicone compound may be replaced by acid labile groups. Z is a di- to hexavalent, non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; Z is a di- to hexavalent, normal or branched hydrocarbon group or non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; x, y and z are integers of 1-5 corresponding to the valence of Z and Z′; R1 is —OCHR—R′—OH or —NHCHR—R′—OH; R2 is alkyl or alkenyl or a monovalent, non-aromatic, polycyclic hydrocarbon or bridged cyclic hydrocarbon group; p1, p2, p3 and p4 are 0 or positive numbers. A resist composition comprising the high molecular weight silicone compound as a base resin is sensitive to actinic radiation and has a high sensitivity and resolution so that it is suitable for microfabrication with electron beams or deep UV. Since the composition has low absorption at the exposure wavelength of an ArF or KrF excimer laser, a finely defined pattern having walls perpendicular to the substrate can be readily formed.

    摘要翻译： 本发明提供了包含式（1）的重复单元并且具有1,000-50,000重均分子量的高分子量硅氧烷化合物。 硅氧烷化合物中的羧基或羧基和羟基的一些或全部氢原子可被酸不稳定基团取代.Z为二价至六价，非芳香族，单环或多环烃或桥环状烃基; Z是二价至六价，正或支链烃基或非芳香族单环或多环烃或桥环状烃基; x，y和z是对应于Z和Z'的化合价的1-5的整数; R 1是-OCHR-R'-OH或-NHCHR-R'-OH; R 2是烷基或烯基或单价，非芳族，多环烃或桥连环烃基; p1，p2，p3和p4为0或正数。 包含作为基础树脂的高分子量硅氧烷化合物的抗蚀剂组合物对光化辐射敏感，并且具有高灵敏度和分辨率，使得它适合于用电子束或深紫外线的微细加工。 由于组成在ArF或KrF准分子激光器的曝光波长处具有低吸收，因此可以容易地形成具有垂直于衬底的壁的精细限定图案。

    High molecular weight silicone compounds resist compositions, and patterning method
    2.
    发明授权
    High molecular weight silicone compounds resist compositions, and patterning method 有权
    高分子量硅氧烷化合物抵抗组合物和图案化方法

    公开(公告)号：US06309796B1

    公开(公告)日：2001-10-30

    申请号：US09129950

    申请日：1998-08-06

    申请人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

    发明人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

    IPC分类号： G03F7075

    CPC分类号： G03F7/0045 ,  C08G77/14 ,  C08G77/38 ,  C08G77/388 ,  C08G77/50 ,  G03F7/0392 ,  G03F7/0757

    摘要： The invention provides a high molecular weight silicone compound comprising recurring units of formula (1) and having a weight average molecular weight of 1,000-50,000. Some or all of the hydrogen atoms of carboxyl groups or carboxyl and hydroxyl groups in the silicone compound may be replaced by acid labile groups. Z is di- to hexavalent, non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; Z′ is a di- to hexavalent, normal or branched hydrocarbon group or non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; x, y and z are integers of 1-5 corresponding to the valence of Z and Z′; R1 is —OCHR—R′ —OH or —NHCHR—R′ —OH; R2 is alkyl or alkenyl or a monovalent, non-aromatic, polycyclic hydrocarbon or bridged cyclic hydrocarbon group; p1, p2, p3 and p4 are 0 or positive numbers. A resist composition comprising the high molecular weight silicone compound as a base resin is sensitive to actinic radiation and has a high sensitivity and resolution so that it is suitable for microfabrication with electron beams or deep UV. Since the composition has low absorption at the exposure wavelength of an ArF or KrF excimer laser, a finely defined pattern having walls perpendicular to the substrate can be readily formed.

    摘要翻译： 本发明提供了包含式（1）的重复单元并且具有1,000-50,000重均分子量的高分子量硅氧烷化合物。 硅烷化合物中的羧基或羧基和羟基的一部分或全部氢原子可被酸不稳定基团取代.Z为二价至六价，非芳香族，单环或多环烃基或桥环状烃基; Z'是二价至六价，正或支链烃基或非芳香族单环或多环烃或桥连环烃基; x，y和z是对应于Z和Z'的化合价的1-5的整数; R 1是-OCHR-R'-OH或-NHCHR-R'-OH; R2是烷基或链烯基或单价，非芳族，多环烃或桥连环烃基; p1，p2，p3和p4为0或正数。 包含作为基础树脂的高分子量硅氧烷化合物的抗蚀剂组合物对光化辐射敏感，并且具有高灵敏度和分辨率，使得它适合于用电子束或深紫外线的微细加工。 由于组成在ArF或KrF准分子激光器的曝光波长处具有低吸收，因此可以容易地形成具有垂直于衬底的壁的精细限定图案。

    High molecular weight silicone compounds, chemically amplified positive resist compositions, and patterning method
    5.
    发明授权
    High molecular weight silicone compounds, chemically amplified positive resist compositions, and patterning method 失效
    高分子量硅氧烷化合物，化学放大正性抗蚀剂组合物和图案化方法

    公开(公告)号：US6066433A

    公开(公告)日：2000-05-23

    申请号：US37023

    申请日：1998-03-09

    申请人： Katsuya Takemura ,  Junji Tsuchiya ,  Ichiro Kaneko ,  Toshinobu Ishihara

    发明人： Katsuya Takemura ,  Junji Tsuchiya ,  Ichiro Kaneko ,  Toshinobu Ishihara

    IPC分类号： C08G77/14 ,  G03F7/004 ,  G03F7/075

    CPC分类号： C08G77/14 ,  G03F7/0045 ,  G03F7/0757 ,  Y10S430/106

    摘要： In a silicone polymer having phenolic hydroxyl groups, the hydrogen atoms of some of the phenolic hydroxyl groups are replaced by acid labile groups of at least one type. The silicone polymer is crosslinked at some of the remaining phenolic hydroxyl groups with crosslinking groups having C--O--C linkages within a molecule and/or between molecules. The silicone polymer has a Mw of 5,000 to 50,000. A chemically amplified positive resist composition comprising the silicone polymer as a base resin has a high sensitivity and resolution so that it is suitable for fine patterning with electron beams or deep UV. Because of improved oxygen plasma etching resistance, the composition is suitable for use in the two-layer resist technique.

    摘要翻译： 在具有酚羟基的硅氧烷聚合物中，一些酚羟基的氢原子被至少一种类型的酸不稳定基团取代。 硅氧烷聚合物在一些剩余的酚羟基上与在分子内和/或分子之间具有C-O-C键的交联基团交联。 有机硅聚合物的Mw为5,000至50,000。 包含作为基础树脂的硅氧烷聚合物的化学放大型正性抗蚀剂组合物具有高灵敏度和分辨率，使其适用于用电子束或深紫外线精细构图。 由于氧等离子体抗蚀刻性能的改善，组合物适用于双层抗蚀剂技术。

    Method for preparing partially tert-butoxylated poly(p-hydroxystyrene)
    7.
    发明授权
    Method for preparing partially tert-butoxylated poly(p-hydroxystyrene) 失效
    部分叔丁氧基化聚（对羟基苯乙烯）

    公开(公告)号：US5580936A

    公开(公告)日：1996-12-03

    申请号：US536119

    申请日：1995-09-29

    申请人： Junji Tsuchiya ,  Katsuya Takemura ,  Osamu Watanabe ,  Yoshihumi Takeda ,  Toshinobu Ishihara

    发明人： Junji Tsuchiya ,  Katsuya Takemura ,  Osamu Watanabe ,  Yoshihumi Takeda ,  Toshinobu Ishihara

    IPC分类号： C08F8/00 ,  C08F8/14 ,  C08F12/00 ,  C08F212/14 ,  G03F7/027

    CPC分类号： C08F8/12 ,  C08F2800/20

    摘要： A partially tert-butoxylated poly(p-hydroxystyrene) is prepared by subjecting poly(p-tert-butoxystyrene) to reaction of eliminating some of the tert-butoxy groups in an organic solvent at a temperature of 30.degree.-100.degree. C. in the presence of an acid catalyst at a molar ratio of acid catalyst/t-BuO group of from 0.050 to 2.0. During the elimination reaction, a change of solubility of the resulting partially tert-butoxylated poly(p-hydroxystyrene) is determined to calculate a degree of elimination of tert-butoxy groups. The reaction is terminated when a desired degree of elimination is reached. Through a simple process, partially tert-butoxylated poly(p-hydroxystyrene) having a well controlled t-BuO content is produced in high yields.

    摘要翻译： 通过使聚（对叔丁氧基苯乙烯）在有机溶剂中在30℃-100℃的温度下除去一些叔丁氧基进行反应来制备部分叔丁氧基化的聚（对羟基苯乙烯） 酸催化剂/ t-BuO基团的摩尔比为0.050至2.0的酸催化剂的存在。 在消除反应期间，测定所得部分叔丁氧基化聚（对羟基苯乙烯）的溶解度的变化，以计算叔丁氧基的消除程度。 当达到所需的消除程度时，终止反应。 通过简单的方法，产生具有良好控制的t-BuO含量的部分叔丁氧基化聚（对羟基苯乙烯），产率高。

    Positive resist composition
    8.
    发明授权
    Positive resist composition 失效
    正抗蚀剂组成

    公开(公告)号：US5612170A

    公开(公告)日：1997-03-18

    申请号：US569659

    申请日：1995-12-08

    申请人： Katsuya Takemura ,  Junji Tsuchiya ,  Toshinobu Ishihara ,  Akinobu Tanaka ,  Yoshio Kawai ,  Jiro Nakamura

    发明人： Katsuya Takemura ,  Junji Tsuchiya ,  Toshinobu Ishihara ,  Akinobu Tanaka ,  Yoshio Kawai ,  Jiro Nakamura

    IPC分类号： G03F7/004 ,  G03F7/075 ,  G03C1/73

    CPC分类号： G03F7/0045 ,  G03F7/0755 ,  G03F7/0757 ,  Y10S430/115 ,  Y10S430/122

    摘要： A positive resist composition based on a silicone polymer contains a photo acid generator which will decompose to generate an acid upon exposure to radiation. The silicone polymer includes hydroxybenzyl units wherein some OH groups are replaced by t-butoxycarbonyl, t-butoxycarbonylmethyl, trimethylsilyl or tetrahydropyranyl groups. In a first form, the photo acid generator is a specific onium salt having at least one phenyl group with a t-alkoxy, t-butoxycarbonyloxy or t-butoxycarbonylmethoxy substituent. In a second form, the composition further contains a nitrogenous compound. In a third form, the composition further contains a dissolution inhibitor in the form of a specific silicone compound. The composition is sensitive to high energy radiation and has high sensitivity and resolution.

    摘要翻译： 基于有机硅聚合物的正型抗蚀剂组合物含有光致酸产生剂，其将在暴露于辐射时分解产生酸。 有机硅聚合物包括其中一些OH基被叔丁氧基羰基，叔丁氧基羰基甲基，三甲基甲硅烷基或四氢吡喃基代替的羟基苄基单元。 在第一种形式中，光酸产生剂是具有至少一个具有叔烷氧基，叔丁氧基羰基氧基或叔丁氧基羰基甲氧基取代基的苯基的特定鎓盐。 在第二种形式中，组合物还含有含氮化合物。 在第三种形式中，组合物还含有特定硅氧烷化合物形式的溶解抑制剂。 该成分对高能辐射敏感，灵敏度高，分辨率高。

    Polymers and chemically amplified positive resist compositions
    9.
    发明授权
    Polymers and chemically amplified positive resist compositions 失效
    聚合物和化学增幅阳性抗蚀剂组合物

    公开(公告)号：US06022665A

    公开(公告)日：2000-02-08

    申请号：US109084

    申请日：1998-07-02

    申请人： Osamu Watanabe ,  Yoshihumi Takeda ,  Junji Tsuchiya ,  Toshinobu Ishihara

    发明人： Osamu Watanabe ,  Yoshihumi Takeda ,  Junji Tsuchiya ,  Toshinobu Ishihara

    IPC分类号： C08F212/14 ,  G03C1/492

    CPC分类号： C08F212/14 ,  Y10S430/115

    摘要： The invention provides a novel polymer comprising a recurring unit of formula (1) wherein R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or acid labile group, at least one R.sup.2 being hydrogen and at least one R.sup.2 being an acid labile group, and n=2 or 3. The polymer's Mw is 3,000-300,000. Blending the polymer as a base resin with an organic solvent and a photoacid generator yields a chemically amplified positive resist composition. ##STR1##

    摘要翻译： 本发明提供一种包含式（1）的重复单元的新型聚合物，其中R 1是氢或甲基，R 2是氢或酸不稳定基团，至少一个R 2是氢，至少一个R 2是酸不稳定基团，n = 聚合物的Mw为3,000-300,000。 将聚合物作为基础树脂与有机溶剂和光酸发生剂混合产生化学放大的正性抗蚀剂组合物。

    Polymers and chemically amplified positive resist compositions
    10.
    发明授权
    Polymers and chemically amplified positive resist compositions 失效
    聚合物和化学增幅阳性抗蚀剂组合物

    公开(公告)号：US5844057A

    公开(公告)日：1998-12-01

    申请号：US630633

    申请日：1996-04-11

    申请人： Osamu Watanabe ,  Yoshihumi Takeda ,  Junji Tsuchiya ,  Toshinobu Ishihara

    发明人： Osamu Watanabe ,  Yoshihumi Takeda ,  Junji Tsuchiya ,  Toshinobu Ishihara

    IPC分类号： C08F212/14 ,  G03C1/492 ,  C08F12/24

    CPC分类号： C08F212/14 ,  Y10S430/115

    摘要： The invention provides a novel polymer comprising a recurring unit of formula. (1) wherein R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or acid labile group, at least one R.sup.2 being hydrogen and at least one R.sup.2 being an acid labile group, and n=2 or 3. The polymer's Mw is 3,000-300,000. Blending the polymer as a base resin with an organic solvent and a photoacid generator yields a chemically amplified positive resist composition. ##STR1##

    摘要翻译： 本发明提供一种包含式的重复单元的新型聚合物。 （1）其中R1是氢或甲基，R2是氢或酸不稳定基团，至少一个R2是氢，至少一个R2是酸不稳定基团，n = 2或3.聚合物的Mw为3,000-300,000。 将聚合物作为基础树脂与有机溶剂和光酸发生剂混合产生化学放大的正性抗蚀剂组合物。 （1）