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1. 发明授权

US06730453B2 High molecular weight silicone compounds, resist compositions, and patterning method 有权
标题翻译：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。

2. 发明授权

US06309796B1 High molecular weight silicone compounds resist compositions, and patterning method 有权
标题翻译：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。

3. 发明授权

US5849461A Chemically amplified positive resist composition 失效
标题翻译：化学放大正光刻胶组合物
公开(公告)号：US5849461A
公开(公告)日：1998-12-15
申请号：US684395
申请日：1996-07-19
申请人： Jun Hatakeyama , Shigehiro Nagura , Kiyoshi Motomi , Takeshi Nagata , Toshinobu Ishihara
发明人： Jun Hatakeyama , Shigehiro Nagura , Kiyoshi Motomi , Takeshi Nagata , Toshinobu Ishihara
IPC分类号： G03F7/004 , G03F7/039 , G03F7/038
CPC分类号： G03F7/039 , G03F7/0045
摘要： In a chemically amplified positive resist composition comprising an organic solvent, an acid labile group-protected resin and a photoacid generator, a compound having a weight average molecular weight of 100-1,000 and at least two phenolic hydroxyl groups in a molecule wherein the hydrogen atom of the phenolic hydroxyl group is partially replaced by an acid labile group in an overall average proportion of 10-80% is blended as a dissolution controller. The resist composition is highly sensitive to actinic radiation, has improved sensitivity and resolution, and is suitable for use in a fine patterning technique and commercially acceptable.
摘要翻译：在包含有机溶剂，酸不稳定基团保护的树脂和光致酸产生剂的化学放大型正性抗蚀剂组合物中，分子中具有重均分子量为100-1,000的化合物和至少两个酚羟基，其中氢原子的酚羟基被酸不稳定基团部分替代，总平均比例为10-80％混合作为溶解控制剂。抗蚀剂组合物对光化辐射高度敏感，具有改进的灵敏度和分辨率，并且适用于精细图案化技术和商业上可接受的。

4. 发明授权

US5750309A Chemically amplified positive resist composition 失效
标题翻译：化学放大正光刻胶组合物
公开(公告)号：US5750309A
公开(公告)日：1998-05-12
申请号：US684481
申请日：1996-07-19
申请人： Jun Hatakeyama , Shigehiro Nagura , Kiyoshi Motomi , Takeshi Nagata , Toshinobu Ishihara
发明人： Jun Hatakeyama , Shigehiro Nagura , Kiyoshi Motomi , Takeshi Nagata , Toshinobu Ishihara
IPC分类号： G03F7/004 , G03F7/039
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106 , Y10S430/111
摘要： In a chemical amplification positive resist composition comprising an organic solvent, a resin and a photoacid generator, at least two polymers having different molecular weights selected from polyhydroxystyrenes having some hydroxyl groups protected with acid labile groups are used. Among the polymers, a high molecular weight polymer has a molecular weight dispersity (Mw1/Mn1) of up to 1.5, and a low molecular weight polymer has a dispersity (Mw2/Mn2) of up to 5.0. The weight average molecular weight ratio Mw1/Mw2 is between 1.5/1 and 10.0/1. The resist composition is highly sensitive to actinic radiation, has improved sensitivity and resolution, and is suitable for use in a fine patterning technique and commercially acceptable.
摘要翻译：在包含有机溶剂，树脂和光致酸发生剂的化学放大正性抗蚀剂组合物中，使用至少两种具有不同分子量的聚合物，其选自具有用酸不稳定基保护的一些羟基的多羟基苯乙烯。在聚合物中，高分子量聚合物的分子量分散性（Mw1 / Mn1）高达1.5，低分子量聚合物的分散性（Mw2 / Mn2）高达5.0。重均分子量Mw1 / Mw2在1.5 / 1和10.0 / 1之间。抗蚀剂组合物对光化辐射高度敏感，具有改进的灵敏度和分辨率，并且适用于精细图案化技术和商业上可接受的。

5. 发明授权

US6030746A Di- and triphenyl monoterpene hydrocarbon derivatives, dissolution inhibitors, and chemically amplified positive resist compositions 失效
标题翻译：二苯基和三苯基单萜烃衍生物，溶解抑制剂和化学增强正性抗蚀剂组合物
公开(公告)号：US6030746A
公开(公告)日：2000-02-29
申请号：US831749
申请日：1997-04-01
申请人： Takeshi Nagata , Satoshi Watanabe , Tsunehiro Nishi , Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
发明人： Takeshi Nagata , Satoshi Watanabe , Tsunehiro Nishi , Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
IPC分类号： C07C43/205 , C07C43/30 , C07C43/303 , C07C43/315 , C07C43/32 , C07C69/28 , C07C69/30 , C07C69/712 , C07C69/96 , C07F7/06 , C07F7/08 , C07F7/18 , G03F7/004 , G03F7/039 , H01L21/027
CPC分类号： C07C43/303 , C07C69/96 , G03F7/0045 , C07C2101/14 , G03F7/039 , Y10S430/118
摘要： Di- or triphenyl monoterpene hydrocarbon derivatives of formula (1) are novel. ##STR1## X is a di- or trivalent monoterpene hydrocarbon group, R.sup.1 to R.sup.3 are hydrogen or an alkyl, alkoxy, alkoxyalkyl, alkenyl or aryl group, R.sup.4 is hydrogen or an acid labile group, at least one R.sup.4 being an acid labile group, letter n is an integer of 1-5, j, k and m are integers of 0-4, n+j+k+m=5, and p is 2 or 3. When used as a dissolution rate regulator, the compound of formula (1) exerts remarkably enhanced dissolution inhibitory effect and minimized light absorption in the deep-UV region. A chemically amplified positive resist composition having the compound of formula (1) blended therein is highly sensitive to actinic radiation such as deep-UV radiation, electron beam and X-ray, especially KrF excimer laser light, and has improved sensitivity, resolution and plasma etching resistance.
摘要翻译：式（1）的二 - 或三苯基单萜烃衍生物是新颖的。 X是二价或三价单萜烃基，R 1至R 3是氢或烷基，烷氧基，烷氧基烷基，烯基或芳基，R 4是氢或酸不稳定基团，至少一个R 4是酸不稳定基团，字母n 是1-5的整数，j，k和m是0-4，n + j + k + m = 5的整数，p是2或3.当用作溶出速率调节剂时，式 1）在深紫外区域发挥显着增强的溶解抑制作用和最小化的光吸收。具有其中混合的式（1）化合物的化学放大正性抗蚀剂组合物对光化辐射如深UV辐射，电子束和X射线，特别是KrF准分子激光具有高度敏感性，并且具有改善的灵敏度，分辨率和等离子体耐腐蚀性。

6. 发明授权

US6048661A Polymeric compounds, chemically amplified positive type resist materials and process for pattern formation 失效
标题翻译：聚合化合物，化学放大正型抗蚀剂材料和图案形成工艺
公开(公告)号：US6048661A
公开(公告)日：2000-04-11
申请号：US33147
申请日：1998-03-02
申请人： Tsunehiro Nishi , Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
发明人： Tsunehiro Nishi , Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
IPC分类号： G03F7/004 , G03F7/039
CPC分类号： G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/11 , Y10S430/111
摘要： Provided are polymeric compounds which, when used as base resins in resist materials, can yield chemical resist materials having high sensitivity, high resolution, a high exposure latitude, and good process adaptability, exhibiting excellent resistance to plasma etching, and giving resist patterns having high thermal resistance, as well as chemically amplified positive type resist materials using such polymeric compounds as base resins. These chemically amplified positive type resist materials use a base resin comprising a polymeric compound having a weight-average molecular weight of 1,000 to 500,000 and having one or more hydroxyl and/or carboxyl groups in the molecule, part or all of the hydrogen atoms of the hydroxyl and/or carboxyl groups being replaced by groups of the following general formula ##STR1## and additionally contain an acid generator, a dissolution inhibitor, a basic compound, and an aromatic compound having a group of the formula .tbd.C--COOH.
摘要翻译：提供了当作为抗蚀剂材料中的基础树脂使用时，可以产生具有高灵敏度，高分辨率，高曝光宽容度和良好的工艺适应性的化学抗蚀剂材料，表现出优异的等离子体蚀刻性，并且具有高抗蚀剂图案的抗蚀剂图案耐热性以及使用这种聚合物作为基础树脂的化学放大正型抗蚀剂材料。这些化学放大正型抗蚀剂材料使用包含重均分子量为1,000至500,000并且在分子中具有一个或多个羟基和/或羧基的聚合化合物的基础树脂，部分或全部氢原子羟基和/或羧基被下列通式的基团取代，另外含有酸产生剂，溶解抑制剂，碱性化合物和具有式3BOND C-COOH基团的芳族化合物。

7. 发明授权

US5985512A Chemically amplified positive resist compositions 失效
标题翻译：化学扩增的正性抗蚀剂组合物
公开(公告)号：US5985512A
公开(公告)日：1999-11-16
申请号：US831750
申请日：1997-04-01
申请人： Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
发明人： Jun Hatakeyama , Shigehiro Nagura , Toshinobu Ishihara
IPC分类号： G03F7/004 , G03F7/039 , H01L21/027
CPC分类号： G03F7/0045 , G03F7/039 , Y10S430/106
摘要： A chemically amplified positive resist composition is prepared by blending (A) an organic solvent, (B) a base resin, and (C) a photoacid generator with a mixture of (1) a nitrogenous organic compound having pKa.gtoreq.7 and a vapor pressure of less than 2 Torr at 100.degree. C. and (2) a nitrogenous organic compound having pKa.gtoreq.7 and a vapor pressure of 2-100 Torr at 100.degree. C. The resist composition has high sensitivity to actinic radiation and high resolution, is developable with aqueous base to form a pattern without a T-top profile by PED and footing on the substrate surface, and is suitable for fine processing.
摘要翻译：通过将（A）有机溶剂，（B）基础树脂和（C）光酸产生剂与（1）具有pKa = 7的含氮有机化合物和在100℃下蒸气压小于2乇，（2）在100℃下pKa> = 7，蒸汽压为2-100乇的含氮有机化合物。抗蚀剂组合物对光化辐射具有高敏感性，高分辨率，可用水性基底显影，通过PED形成图案，并且在基材表面上形成基底，并适用于精细加工。

8. 发明授权

US5972560A High molecular weight silicone compound, chemically amplified positive resist composition and patterning method 失效
标题翻译：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：US5972560A
公开(公告)日：1999-10-26
申请号：US16448
申请日：1998-01-30
申请人： Ichiro Kaneko , Mutsuo Nakashima , Toshinobu Ishihara , Junji Tsuchiya , Jun Hatakeyama , Shigehiro Nagura
发明人： Ichiro Kaneko , Mutsuo Nakashima , Toshinobu Ishihara , Junji Tsuchiya , Jun Hatakeyama , Shigehiro Nagura
IPC分类号： C08G77/50 , C08L83/14 , G03F7/004 , G03F7/075 , C08G77/04
CPC分类号： G03F7/0045 , C08G77/50 , C08L83/14 , G03F7/0757
摘要： The invention provides a high molecular weight silicone compound comprising recurring units of the general formula (1) and having a weight average molecular weight of 1,000-50,000. ##STR1## Z is a di- to hexavalent, monocyclic or polycyclic hydrocarbon group or bridged cyclic hydrocarbon group of 5-12 carbon atoms, R.sup.1 is a substituted or unsubstituted alkyl or alkenyl group of 1-8 carbon atoms, R.sup.2 is an acid labile group, m is 0 or an integer, n is an integer, satisfying m+n.ltoreq.5, x is an integer, p1 and p2 are positive numbers, q is 0 or a positive number, satisfying 0
摘要翻译：本发明提供了包含通式（1）的重复单元并具有1,000-50,000的重均分子量的高分子量硅氧烷化合物。 Z是5至12个碳原子的二至六价单环或多环烃基或桥环状烃基，R1是取代或未取代的1-8个碳原子的烷基或链烯基，R2是酸不稳定基团，m 是0或整数，n是整数，满足m + n <5，x是整数，p1和p2是正数，q是0或正数，满足0

9. 发明授权

US6117621A Patterning method 失效
标题翻译：图案化方法
公开(公告)号：US6117621A
公开(公告)日：2000-09-12
申请号：US48022
申请日：1998-03-26
申请人： Jun Hatakeyama , Shigehiro Nagura
发明人： Jun Hatakeyama , Shigehiro Nagura
IPC分类号： G03F7/004 , G03F7/039 , G03F7/30
CPC分类号： G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/111
摘要： A method for patterning a chemically amplified positive resist material comprising a base polymer having acid labile groups which are eliminated by acid, a photoacid generator and an organic solvent, in which the resist material is applied onto a substrate to a uniform thickness so as to form a resist film that is subsequently exposed, baked, then developed with a developer to form a positive pattern is characterized by using as the base polymer a mixture of at least two base polymers having mutually differing acid labile groups or a base polymer having at least two mutually differing acid labile groups on the same molecule and adjusting the types of the mutually differing acid labile groups and their contents within the base polymer such that, when the chemically amplified positive resist material is applied onto a substrate to a uniform thickness so as to form a resist film that is subsequently exposed, baked, then dissolved with a developer, the exposure E1 which results in an average dissolution rate of 100 .ANG./s for 500 .ANG. from the surface of the resist film toward the substrate and the exposure E2 which results in an average dissolution rate of 100 .ANG./s for 1000 .ANG. from the surface of the substrate toward the resist film surface satisfy the relationship: -0.2
摘要翻译：一种用于图案化化学放大正型抗蚀剂材料的方法，其包括具有酸不稳定基团的基础聚合物，其被酸，光致酸产生剂和有机溶剂除去，其中将抗蚀剂材料施加到基底上以形成均匀的厚度，以形成随后用显影剂曝光，烘烤，然后显影以形成阳性图案的抗蚀剂膜的特征在于使用至少两种具有相互不同的酸不稳定基团的基础聚合物或具有至少两个在相同分子上相互不同的酸不稳定基团并调节相互不同的酸不稳定基团的类型及其在基础聚合物内的含量，使得当将化学放大的正性抗蚀剂材料施加到基底上以均匀的厚度形成随后暴露，烘烤，然后用显影剂溶解的抗蚀剂膜，曝光E1导致平均从抗蚀剂膜的表面向衬底的500 ANGSTROM的100安培/秒的Ge溶解速率和曝光E2，其导致从基板表面到抗蚀剂膜的1000安培姆的平均溶解速率为100安培表面满足关系：-0.2 <（E2-E1）/ E2 <0.2。

10. 发明授权

US06274286B1 Resist compositions 失效
标题翻译：抗蚀剂组合物
公开(公告)号：US06274286B1
公开(公告)日：2001-08-14
申请号：US09105003
申请日：1998-06-26
申请人： Jun Hatakeyama , Tsunehiro Nishi , Takeshi Nagata , Shigehiro Nagura
发明人： Jun Hatakeyama , Tsunehiro Nishi , Takeshi Nagata , Shigehiro Nagura
IPC分类号： G03F7004
CPC分类号： G03F7/0045 , Y10S430/106
摘要： A chemically amplified positive resist composition comprising at least one basic compound of the following general formula (1) or (2): wherein R1, R2, R3, R7, and R8 are independently normal, branched or cyclic alkylene groups having 1 to 20 carbon atoms, R4, R5, R6, R9, and R10 are independently hydrogen, alkyl groups having 1 to 20 carbon atoms or amino groups, R4 and R5, R5 and R6, R4 and R6, or R8, R5 and R5, and R9 and R10, taken together, may form a ring, letters k, m and n are integers of 0 to 20, with the proviso that hydrogen is excluded from R4, R5, R6, R9 and R10 when k, m or n is equal to 0. The resist compositions of the present invention are effective for preventing resist films from thinning and for increasing the focus margin of an isolated pattern.
摘要翻译：一种化学放大正型抗蚀剂组合物，其包含至少一种下列通式（1）或（2）的碱性化合物：其中R 1，R 2，R 3，R 7和R 8独立地为具有1至20个碳的正，支链或环状亚烷基原子，R 4，R 5，R 6，R 9和R 10独立地是氢，具有1至20个碳原子的烷基或氨基，R 4和R 5，R 5和R 6，R 4和R 6，或R 8，R 5和R 5， R 10一起可以形成环，字母k，m和n是0至20的整数，条件是当k，m或n等于0时，从R4，R5，R6，R9和R10排除氢。本发明的抗蚀剂组合物对于防止抗蚀剂膜变薄和增加隔离图案的聚焦边缘是有效的。

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