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1. 发明授权

US06517992B1 N-sulfonyloxyimide compound and radiation-sensitive resin composition using the same 有权
标题翻译： N-磺酰氧基酰亚胺化合物和使用其的辐射敏感性树脂组合物
公开(公告)号：US06517992B1
公开(公告)日：2003-02-11
申请号：US09707939
申请日：2000-11-08
申请人： Yong Wang , Eiichi Kobayashi , Masaaki Miyaji , Jun Numata , Tsutomu Shimokawa
发明人： Yong Wang , Eiichi Kobayashi , Masaaki Miyaji , Jun Numata , Tsutomu Shimokawa
IPC分类号： G03F7004
CPC分类号： C07D207/46 , C07D209/76 , G03F7/0045 , G03F7/038 , G03F7/039 , Y10S430/121
摘要： An N-sulfonyloxyimide compound having the formula (1): wherein X represents a single bond or a double bond, Y and Z represent a hydrogen atom or others and may combine to form a cyclic structure; and R is a group having the formula (2): wherein X1 represents an organic group having an ester linkage, R1 represents an alkyl group or an alkoxyl group; and m is an integer of 1 to 11 and n is an integer of 0 to 10, satisfying m+n≦11; and chemically amplified positive and negative radiation-sensitive resin compositions using the compound are provided. The N-sulfonyloxyimide compound is a good radiation-sensitive acid-generating agent, has no problem of volatilization or side reaction, can keep dark reaction from taking place during the storage. The compound is useful as a component of radiation-sensitive chemically amplified resists.
摘要翻译：具有式（1）的N-磺酰氧基酰亚胺化合物：其中X表示单键或双键，Y和Z表示氢原子等，可以结合形成环状结构; 并且R是具有式（2）的基团：其中X1表示具有酯键的有机基团，R1表示烷基或烷氧基; m为1〜11的整数，n为0〜10的整数，满足m + n <11。并提供使用该化合物的化学放大的正和负辐射敏感性树脂组合物。 N-磺酰氧基酰亚胺化合物是良好的辐射敏感性产酸剂，不存在挥发或副反应的问题，能够保持保存期间的黑色反应。该化合物可用作辐射敏感的化学放大抗蚀剂的组分。

2. 发明授权

US07202016B2 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US07202016B2
公开(公告)日：2007-04-10
申请号：US11116269
申请日：2005-04-28
申请人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
发明人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
IPC分类号： G03F7/004
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/122
摘要： A chemically amplified radiation-sensitive resin composition comprising a specific copolymer and a photoacid generator, wherein the copolymer contains the following recurring unit (1) and/or the recurring unit (2), and the recurring unit (3-1), wherein R1 is a hydrogen or methyl, R2 is a C4-10 tertiary alkyl, R3 and R4 are a hydrogen, C1-12 alkyl, C6-15 aromatic, C1-12 alkoxyl, or R3 and R4 may form, in combination and together with the nitrogen atom with which the R3 and R4 groups bond, a C3-15 cyclic structure, provided that R3 and R4 are not a hydrogen atom at the same time. The composition effectively responds to various radiations, exhibits excellent resolution and pattern configuration and minimal iso-dense bias, and can form fine patterns at a high precision and in a stable manner.
摘要翻译：一种包含特定共聚物和光致酸发生剂的化学放大的辐射敏感性树脂组合物，其中共聚物含有以下重复单元（1）和/或重复单元（2）和重复单元（3-1），

3. 发明授权

US06933094B2 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06933094B2
公开(公告)日：2005-08-23
申请号：US09953941
申请日：2001-09-18
申请人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
发明人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
IPC分类号： G03F7/004 , G03F7/038 , G03F7/039
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/122
摘要： A chemically amplified radiation-sensitive resin composition comprising a specific copolymer and a photoacid generator, wherein the copolymer contains the following recurring unit (1) and/or the recurring unit (2), and the recurring unit (3-1), wherein R1 is a hydrogen or methyl, R2 is a C4-10 tertiary alkyl, R3and R4 are a hydrogen, C1-12 alkyl, C6-15 aromatic, C1-12 alkoxyl, or R3 and R4 may form, in combination and together with the nitrogen atom with which the R3 and R4 groups bond, a C3-15 cyclic structure, provided that R3 and R4 are not a hydrogen atom at the same time. The composition effectively responds to various radiations, exhibits excellent resolution and pattern configuration and minimal iso-dense bias, and can form fine patterns at a high precision and in a stable manner.
摘要翻译：包含特定共聚物和光酸产生剂的化学放大的辐射敏感性树脂组合物，其中所述共聚物包含以下重复单元（1）和/或重复单元（2）和重复单元（3-1），其中R 1是氢或甲基，R 2是C 4-10叔烷基，R 3和R 3 H 4是氢，C 1-12烷基，C 6-15芳族，C 1-12烷氧基，，或R 3和R 4可以与R 3和R 4的氮原子组合形成，基团键合，C 3-15-15环状结构，条件是R 3和R 4不是氢原子同时。该组合物有效响应各种辐射，显示出优异的分辨率和图案配置以及最小的等密度偏差，并能以高精度和稳定的方式形成精细图案。

4. 发明申请

US20050214680A1 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US20050214680A1
公开(公告)日：2005-09-29
申请号：US11116269
申请日：2005-04-28
申请人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
发明人： Masaaki Miyaji , Tomoki Nagai , Yuji Yada , Jun Numata , Yukio Nishimura , Masafumi Yamamoto , Hiroyuki Ishii , Toru Kajita , Tsutomu Shimokawa
IPC分类号： G03F7/004 , G03F7/038 , G03F7/039 , G03C1/76
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/122
摘要： A chemically amplified radiation-sensitive resin composition comprising a specific copolymer and a photoacid generator, wherein the copolymer contains the following recurring unit (1) and/or the recurring unit (2), and the recurring unit (3-1), wherein R1 is a hydrogen or methyl, R2 is a C4-10 tertiary alkyl, R3 and R4 are a hydrogen, C1-12 alkyl, C6-15 aromatic, C1-12 alkoxyl, or R3 and R4 may form, in combination and together with the nitrogen atom with which the R3 and R4 groups bond, a C3-15 cyclic structure, provided that R3 and R4 are not a hydrogen atom at the same time. The composition effectively responds to various radiations, exhibits excellent resolution and pattern configuration and minimal iso-dense bias, and can form fine patterns at a high precision and in a stable manner.
摘要翻译：包含特定共聚物和光酸产生剂的化学放大的辐射敏感性树脂组合物，其中所述共聚物包含以下重复单元（1）和/或重复单元（2）和重复单元（3-1），其中R 1是氢或甲基，R 2是C 4-10叔烷基，R 3和R 3 H 4是氢，C 1-12烷基，C 6-15芳族，C 1-12烷氧基，，或R 3和R 4可以与R 3和R 4的氮原子组合形成，基团键合，C 3-15-15环状结构，条件是R 3和R 4不是氢原子同时。该组合物有效响应各种辐射，显示出优异的分辨率和图案配置以及最小的等密度偏差，并能以高精度和稳定的方式形成精细图案。

5. 发明授权

US06821705B2 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06821705B2
公开(公告)日：2004-11-23
申请号：US10132249
申请日：2002-04-26
申请人： Tomoki Nagai , Jun Numata , Eiichi Kobayashi , Tsutomu Shimokawa
发明人： Tomoki Nagai , Jun Numata , Eiichi Kobayashi , Tsutomu Shimokawa
IPC分类号： G03F7039
CPC分类号： G03F7/0392 , G03F7/0045 , Y10S430/121
摘要： A radiation-sensitive resin composition comprising (A) a compound of the following formula (1), (R1, R2, and R3 is hydrogen, hydroxyl group, or monovalent organic group and R4 is monovalent acid-dissociable group), (B) an alkali insoluble or scarcely soluble resin comprising a recurring unit of the following formula (2), (R5 is hydrogen or monovalent organic group, R′ hydrogen or methyl, n 1-3, m 0-3) and a recurring unit containing acid-dissociable group, and (C) a photoacid generator. The resin composition is useful as a chemically amplified resist, exhibits high sensitivity, resolution, radiation transmittance, and surface smoothness, and is free from the problem of partial insolublization during overexposure.
摘要翻译：一种辐射敏感性树脂组合物，其包含（A）下式（1）的化合物，（R 1，R 2和R 3）是氢，羟基或一价有机基团，R 4 （B）一种碱不溶性或几乎不溶的树脂，其包含下式（2）的重复单元，（R 5是氢或一价有机基团，R'氢或甲基，n 1-3，m 0-3）和含有酸解离基团的重复单元，和（C）光酸产生剂。树脂组合物可用作化学放大抗蚀剂，显示出高灵敏度，分辨率，辐射透射率和表面光滑度，并且在过度曝光期间不存在部分不溶性的问题。

6. 发明授权

US06623907B2 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06623907B2
公开(公告)日：2003-09-23
申请号：US09774714
申请日：2001-02-01
申请人： Jun Numata , Aki Suzuki , Hiromichi Hara , Norihiro Natsume , Kiyoshi Murata , Masafumi Yamamoto , Akimasa Soyano , Toru Kajita , Tsutomu Shimokawa
发明人： Jun Numata , Aki Suzuki , Hiromichi Hara , Norihiro Natsume , Kiyoshi Murata , Masafumi Yamamoto , Akimasa Soyano , Toru Kajita , Tsutomu Shimokawa
IPC分类号： G03F7004
CPC分类号： G03F7/0045 , G03F7/038 , G03F7/039 , Y10S430/111 , Y10S430/128
摘要： A positive-tone radiation-sensitive resin composition comprising: (A) a low molecular weight compound having at least one amino group in which the nitrogen atom has at least one hydrogen atom bonded thereto and at least one of the hydrogen atoms is replaced by a t-butoxycarbonyl group, (B) a photoacid generator, and (C-1) a resin insoluble or scarcely soluble in alkali which is protected by an acid-dissociable group and becomes soluble in alkali when the acid-dissociable group dissociates or (C-2) an alkali-soluble resin and an alkali solubility control agent is disclosed. Also disclosed is a negative-tone radiation-sensitive resin composition comprising the low molecular weight compound (A), the photoacid generator (B), an alkali-soluble resin (D), and a compound capable of crosslinking with the alkali-soluble resin in the presence of an acid(E). The composition are useful as a chemically amplified resist which effectively responds to various radiations, exhibits superior sensitivity and resolution, forms fine patterns at a high precision and in a stable manner even if the patterns are isolated line patterns.
摘要翻译：一种正色辐射敏感性树脂组合物，其包含：（A）具有至少一个氨基的低分子量化合物，其中所述氮原子具有与其键合的至少一个氢原子，并且至少一个氢原子被叔丁氧基羰基，（B）光酸产生剂和（C-1）不溶于或几乎不溶于碱的树脂，其被酸解离基团保护并且当酸解离基解离时变得可溶于碱，或（C -2）碱溶性树脂和碱溶性控制剂。还公开了包含低分子量化合物（A），光酸产生剂（B），碱溶性树脂（D）和能够与碱溶性树脂交联的化合物的负色辐射敏感性树脂组合物在酸（E）的存在下。该组合物可用作化学放大抗蚀剂，其有效地响应各种辐射，表现出优异的灵敏度和分辨率，即使图案是隔离线图案，也以高精度和稳定的方式形成精细图案。

7. 发明授权

US06465150B1 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06465150B1
公开(公告)日：2002-10-15
申请号：US09686930
申请日：2000-10-12
申请人： Jun Numata , Shirou Kusumoto , Eiichi Kobayashi
发明人： Jun Numata , Shirou Kusumoto , Eiichi Kobayashi
IPC分类号： G03F7004
CPC分类号： G03F7/0045 , G03F7/0392 , Y10S430/115 , Y10S430/122
摘要： A radiation-sensitive resin composition exhibiting high sensitivity to various types of radiation and capable of forming a minute pattern with sufficient resolution and depth of field and small surface roughness in various types of patterns such as a dense line pattern, isolated line pattern, or contact holes, particularly in line-type patterns. The resin composition comprises (A) an aromatic sulfonic acid onium salt compound consisting of a 2,4-difluorobenzenesulfonic acid anion, 4-trifluoromethylbenzenesulfonic acid anion, or 2-trifluoromethylbenzenesulfonic acid anion, and an onium cation of sulfur or iodonium, and (B) a copolymer represented by a 4-hydroxystyrene/4-t-butoxystyrene copolymer and a 4-hydroxystyrene/4-(1′-ethoxyethoxy)styrene copolymer.
摘要翻译：对各种类型的辐射具有高灵敏度并且能够形成具有足够的分辨率和景深以及诸如密集线图案，隔离线图案或接触的各种图案中的小表面粗糙度的微小图案的辐射敏感性树脂组合物孔，特别是线型图案。树脂组合物包含（A）由2,4-二氟苯磺酸阴离子，4-三氟甲基苯磺酸阴离子或2-三氟甲基苯磺酸阴离子和硫或碘鎓的鎓阳离子组成的芳族磺酸鎓盐化合物和（B ）由4-羟基苯乙烯/ 4-叔丁氧基苯乙烯共聚物和4-羟基苯乙烯/ 4-（1'-乙氧基乙氧基）苯乙烯共聚物表示的共聚物。

8. 发明授权

US06846607B2 Carbazole derivative and chemically amplified radiation-sensitive resin composition 有权
标题翻译：咔唑衍生物和化学放大敏感树脂组合物
公开(公告)号：US06846607B2
公开(公告)日：2005-01-25
申请号：US10087735
申请日：2002-03-05
申请人： Tomoki Nagai , Jun Numata , Shirou Kusumoto , Eiichi Kobayashi
发明人： Tomoki Nagai , Jun Numata , Shirou Kusumoto , Eiichi Kobayashi
IPC分类号： C07D209/86 , C08F8/30 , G03F7/004 , G03F7/039 , H01L21/027 , G03F7/30
CPC分类号： C08F8/30 , C07D209/86 , G03F7/0045 , G03F7/0392 , Y10S430/106 , Y10S430/111
摘要： A carbazole derivative of the following formula (1), wherein R1 and R2 individually represent a hydrogen atom or a monovalent organic group, or R1 and R2 form, together with the carbon atom to which R1 and R2 bond, a divalent organic group having a 3-8 member carbocyclic structure or a 3-8 member heterocyclic structure, and R3 represents a hydrogen atom or a monovalent organic group. The carbazole derivative is suitable as an additive for increasing sensitivity of a chemically amplified resist. A chemically amplified radiation-sensitive resin composition, useful as a chemically amplified resist, comprising the carbazole derivative is also disclosed.
摘要翻译：下式（1）的咔唑衍生物，其中R 1和R 2分别代表氢原子或一价有机基团，或R 1和R 2与碳原子一起形成 R 1和R 2键，具有3-8个碳环结构或3-8元杂环结构的二价有机基团，R 3表示氢原子或一价有机基团。咔唑衍生物适合作为增加化学增幅抗蚀剂敏感性的添加剂。还公开了包含咔唑衍生物的化学增幅辐射敏感性树脂组合物，其可用作化学增幅抗蚀剂。

9. 发明授权

US06506537B2 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06506537B2
公开(公告)日：2003-01-14
申请号：US09878274
申请日：2001-06-12
申请人： Eiichi Kobayashi , Jun Numata , Mikio Yamachika , Masafumi Yamamoto
发明人： Eiichi Kobayashi , Jun Numata , Mikio Yamachika , Masafumi Yamamoto
IPC分类号： G03F7004
CPC分类号： G03F7/0758 , G03F7/0045 , G03F7/039 , Y10S430/106 , Y10S430/111
摘要： A positive-type radiation-sensitive resin composition is provided. The composition includes: (A) a low-molecular compound comprising a compound having at least one amino group having one or two hydrogen atom(s) bonded to the nitrogen atom; at least one hydrogen atom the amino group has having been substituted with a t-butoxycarbonyl group; (B) a radiation-sensitive acid generator; and (C) a silicon-atom-containing resin comprising an alkali-insoluble or alkali-slightly-soluble resin having been protected with an acid-cleavable group; the resin being capable of turning soluble in alkali upon cleavage of the acid-cleavable group. This radiation-sensitive resin composition is effectively responsive to radiations of various types, has superior sensitivity and resolution and also a superior long-term storage stability, and is useful as a positive-type chemically amplified resist.
摘要翻译：提供正型辐射敏感性树脂组合物。该组合物包括：（A）包含具有至少一个具有与氮原子键合的一个或两个氢原子的氨基的化合物的低分子化合物; 至少一个氢原子已经被叔丁氧基羰基取代;（B）辐射敏感性酸产生剂; 和（C）含有硅原子的树脂，其包含用酸可裂解基团保护的碱不溶性或碱 - 微溶性树脂; 该树脂在切割酸可分解基团时能够转变为碱溶性。该辐射敏感性树脂组合物对各种辐射有效响应，具有优异的灵敏度和分辨率，并且还具有优异的长期储存稳定性，并且可用作正型化学放大抗蚀剂。

10. 发明授权

US06280900B1 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US06280900B1
公开(公告)日：2001-08-28
申请号：US09558068
申请日：2000-04-26
申请人： Takashi Chiba , Jun Numata
发明人： Takashi Chiba , Jun Numata
IPC分类号： G03F7039
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106 , Y10S430/111
摘要： A radiation-sensitive resin composition comprising (a) a resin represented by a copolymer of p-hydroxystyrene and t-butyl (meth)acrylate and a copolymer of p-hydroxystyrene and p-t-butoxystyrene, (b) a photoacid generator, and (c) a quaternary ammonium salt compound represented by tetramethylammonium adamantanecarboxylate, tetramethylammonium oxalate, tetraethylammonium pyruvate. The radiation-sensitive resin composition is capable of producing a rectangular resist pattern while preventing the top edge of the pattern from rounding, which is a big problem in microprocessing of design dimensions of about 0.20 &mgr;m with a thin film. The radiation-sensitive resin composition is highly sensitive to deep ultraviolet radiation, X-rays, and charged particle rays and exhibits excellent sensitivity, resolution, and the like.
摘要翻译：一种辐射敏感性树脂组合物，其包含（a）由对羟基苯乙烯和（甲基）丙烯酸叔丁酯的共聚物表示的树脂和对羟基苯乙烯和对 - 丁氧基苯乙烯的共聚物，（b）光酸产生剂和（c ）由四甲基金刚烷羧酸甲酯，草酸四甲基铵，丙酮酸四乙基铵表示的季铵盐化合物。辐射敏感性树脂组合物能够制造矩形抗蚀剂图案，同时防止图案的顶部边缘变圆，这是用薄膜设计尺寸为约0.20μm的微加工的大问题。辐射敏感性树脂组合物对深紫外线辐射，X射线和带电粒子射线高度敏感，并且具有优异的灵敏度，分辨率等。

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