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1. 发明授权

US08043786B2 Acid generators, sulfonic acids, sulfonyl halides, and radiation sensitive resin compositions 有权
标题翻译：酸产生剂，磺酸，磺酰卤和辐射敏感性树脂组合物
公开(公告)号：US08043786B2
公开(公告)日：2011-10-25
申请号：US10547769
申请日：2004-02-20
申请人： Satoshi Ebata , Yong Wang , Isao Nishimura
发明人： Satoshi Ebata , Yong Wang , Isao Nishimura
IPC分类号： G03F7/039 , G03F7/038 , C07C317/04 , C07C309/80
CPC分类号： C07C309/19 , C07C309/17 , C07C309/23 , C07C381/12 , C07C2602/42 , C07C2603/86 , C07D207/46 , G03F7/0045 , G03F7/0382 , G03F7/0392 , G03F7/0397 , G03F7/0757 , Y10S430/106 , Y10S430/111 , Y10S430/115 , Y10S430/122 , Y10S430/126
摘要： The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl; R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5. Among the radiation-sensitive resin compositions, a positive one contains a resin having acid-dissociable groups in addition to the above acid generator, while a negative one contains an alkali-soluble resin and a crosslinking agent in addition to the acid generator.
摘要翻译：本发明提供了新颖的酸产生剂，其在人体内的可燃性和积聚中是无问题的，并且可以产生具有高酸度和高沸点的酸，并且在抗蚀剂涂膜中显示适当短的扩散长度，并且允许形成抗蚀剂图案，具有极好的平滑性依赖于掩模图案的致密度; 酸产生器产生的磺酸; 用于合成酸发生剂的原料的磺酰卤; 和含有酸发生剂的辐射敏感性树脂组合物。酸产生剂具有由通式（I）表示的结构，其中R 1是一价取代基，例如烷氧基羰基，烷基磺酰基或烷氧基磺酰基; R2至R4各自为氢或烷基; k为0以上的整数; 并且n为0〜5的整数。在这些辐射敏感性树脂组合物中，除了上述酸产生剂之外，阳性物质含有具有酸解离基团的树脂，而负极性物质含有碱溶性树脂和交联除酸产生剂外还可加入。

2. 发明申请

US20070054214A1 Acid generators, sulfonic acids, sulfonyl halides, and radiation sensitive resin compositions 有权
标题翻译：酸产生剂，磺酸，磺酰卤和辐射敏感性树脂组合物
公开(公告)号：US20070054214A1
公开(公告)日：2007-03-08
申请号：US10547769
申请日：2004-02-20
申请人： Satoshi Ebata , Yong Wang , Isao Nishimura
发明人： Satoshi Ebata , Yong Wang , Isao Nishimura
IPC分类号： G03C1/00
CPC分类号： C07C309/19 , C07C309/17 , C07C309/23 , C07C381/12 , C07C2602/42 , C07C2603/86 , C07D207/46 , G03F7/0045 , G03F7/0382 , G03F7/0392 , G03F7/0397 , G03F7/0757 , Y10S430/106 , Y10S430/111 , Y10S430/115 , Y10S430/122 , Y10S430/126
摘要： The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl, R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5. Among the radiation-sensitive resin compositions, a positive one contains a resin having acid-dissociable groups in addition to the above acid generator, while a negative one contains an alkali-soluble resin and a crosslinking agent in addition to the acid generator.
摘要翻译：本发明提供了新颖的酸产生剂，其在人体内的可燃性和积聚中是无问题的，并且可以产生具有高酸度和高沸点的酸，并且在抗蚀剂涂膜中显示适当短的扩散长度，并且允许形成抗蚀剂图案，具有极好的平滑性依赖于掩模图案的致密度; 酸产生器产生的磺酸; 用于合成酸发生剂的原料的磺酰卤; 和含有酸发生剂的辐射敏感性树脂组合物。酸产生剂具有由通式（I）表示的结构，其中R 1是一价取代基，例如烷氧基羰基，烷基磺酰基或烷氧基磺酰基，R 2至R“ > 4个各自为氢或烷基; k为0以上的整数; 并且n为0〜5的整数。在这些辐射敏感性树脂组合物中，除了上述酸产生剂之外，阳性物质含有具有酸解离基团的树脂，而负极性物质含有碱溶性树脂和交联除酸产生剂外还可加入。

3. 发明申请

US20060141383A1 Sulfonium salts, radiation- sensitive acid generators, and positive radiator-sensitive resin compositions 有权
标题翻译：锍盐，辐射敏感酸产生剂和阳离子敏感树脂组合物
公开(公告)号：US20060141383A1
公开(公告)日：2006-06-29
申请号：US10543092
申请日：2004-01-09
申请人： Takashi Miyamatsu , Hirokazu Niwata , Satoshi Ebata , Yong Wang
发明人： Takashi Miyamatsu , Hirokazu Niwata , Satoshi Ebata , Yong Wang
IPC分类号： G03C1/76
CPC分类号： C07D333/72 , C07D333/46 , C07D333/78 , G03F7/0045 , G03F7/0392 , G03F7/0397 , Y10S430/106 , Y10S430/111 , Y10S430/123
摘要： A sulfonium salt compound excelling in transparency to deep ultraviolet rays at a wavelength of 220 nm or less, exhibiting well-balanced excellent performance such as sensitivity, resolution, pattern form, LER, and storage stability when used as a photoacid generator, a photoacid generator comprising the sulfonium salt compound, and a positive-tone radiation-sensitive resin composition containing the photoacid generator. The sulfonium salt compound is shown by the following formula (I), wherein R1 represents a halogen atom, an alkyl group, a monovalent alicyclic hydrocarbon group, an alkoxyl group, or —OR3 group, wherein R3 is a monovalent alicyclic hydrocarbon group, R2 represents a (substituted)-alkyl group or two or more R2 groups form a cyclic structure, p is 0-7, q is 0-6, n is 0-3, and X− indicates a sulfonic acid anion. The positive-tone radiation-sensitive resin composition comprises (A) a photoacid generator of the sulfonium-salt compound and (B) an acid-dissociable group-containing resin.
摘要翻译：对于220nm以下的波长的紫外线的透明性优异的锍盐化合物，当用作光致酸产生剂，光致酸发生剂时，具有良好的平衡性，例如灵敏度，分辨率，图案形式，LER和储存稳定性包含锍盐化合物和含有光酸产生剂的正色散辐射敏感性树脂组合物。锍盐化合物由下式（I）表示，其中R 1表示卤素原子，烷基，一价脂环族烃基，烷氧基或-OR 3 其中R 3是一价脂环族烃基，R 2表示（取代的） - 烷基或两个或更多个R 2， / SUP>基团形成环状结构，p为0-7，q为0-6，n为0-3，X为 - 表示磺酸阴离子。正色辐射敏感性树脂组合物包含（A）锍盐化合物的光酸产生剂和（B）含酸解离基团的树脂。

4. 发明授权

US06908722B2 Acid generator, sulfonic acid, sulfonic acid derivatives and radiation-sensitive resin composition 有权
标题翻译：酸产生剂，磺酸，磺酸衍生物和辐射敏感树脂组合物
公开(公告)号：US06908722B2
公开(公告)日：2005-06-21
申请号：US10183441
申请日：2002-06-28
申请人： Satoshi Ebata , Eiji Yoneda , Tomoki Nagai , Tatsuya Toneri , Yong Wang , Haruo Iwasawa , Yukio Nishimura
发明人： Satoshi Ebata , Eiji Yoneda , Tomoki Nagai , Tatsuya Toneri , Yong Wang , Haruo Iwasawa , Yukio Nishimura
IPC分类号： C07C309/17 , C07C309/19 , C07C309/23 , C07C381/12 , C07D333/46 , C07D333/78 , C07D335/02 , C07D347/00 , G03F7/004 , G03F7/039 , G03F7/075 , G03F7/00
CPC分类号： C07C309/23 , C07C309/17 , C07C309/19 , C07C381/12 , C07C2602/42 , C07C2603/86 , C07D333/46 , C07D333/78 , C07D335/02 , C07D347/00 , G03F7/0045 , G03F7/0392 , G03F7/0757 , Y10S430/114 , Y10S430/115
摘要： A novel photoacid generator containing a structure of the following formula (I), wherein R is a monovalent organic group with a fluorine content of 50 wt % or less, a nitro group, a cyano group, or a hydrogen atom, and Z1 and Z2 are individually a fluorine atom or a linear or branched perfluoroalkyl group having 1-10 carbon atoms, is provided. When used in a chemically amplified radiation-sensitive resin composition, the photoacid generator exhibits high transparency, comparatively high combustibility, and no bioaccumulation, and produces an acid exhibiting high acidity, high boiling point, moderately short diffusion length in the resist coating, and low dependency to mask pattern density.
摘要翻译：一种含有下式（I）的结构的新型光酸产生剂，其中R为氟含量为50重量％以下的一价有机基团，硝基，氰基或氢原子，Z ^{1和Z 2各自独立地为氟原子或具有1-10个碳原子的直链或支链全氟烷基。当用于化学增强的辐射敏感性树脂组合物中时，光致酸产生剂显示出高透明度，较高的可燃性，并且没有生物累积性，并且产生在抗蚀涂层中表现出高酸度，高沸点，适度短扩散长度的酸，以及低对掩模图案密度的依赖。}

5. 发明授权

US07371503B2 Sulfonium salt compound, photoacid generator, and positive-tone radiation-sensitive resin composition 有权
标题翻译：锍盐化合物，光酸产生剂和正色散辐射敏感树脂组合物
公开(公告)号：US07371503B2
公开(公告)日：2008-05-13
申请号：US10543092
申请日：2004-01-09
申请人： Takashi Miyamatsu , Hirokazu Niwata , Satoshi Ebata , Yong Wang
发明人： Takashi Miyamatsu , Hirokazu Niwata , Satoshi Ebata , Yong Wang
IPC分类号： G03F7/004 , C07D331/04 , C07D333/46 , C07D335/04
CPC分类号： C07D333/72 , C07D333/46 , C07D333/78 , G03F7/0045 , G03F7/0392 , G03F7/0397 , Y10S430/106 , Y10S430/111 , Y10S430/123
摘要： A sulfonium salt compound excelling in transparency to deep ultraviolet rays at a wavelength of 220 nm or less, exhibiting well-balanced excellent performance such as sensitivity, resolution, pattern form, LER, and storage stability when used as a photoacid generator, a photoacid generator comprising the sulfonium salt compound, and a positive-tone radiation-sensitive resin composition containing the photoacid generator.The sulfonium salt compound is shown by the following formula (I), wherein R1 represents a halogen atom, an alkyl group, a monovalent alicyclic hydrocarbon group, an alkoxyl group, or —OR3 group, wherein R3 is a monovalent alicyclic hydrocarbon group, R2 represents a (substituted)-alkyl group or two or more R2 groups form a cyclic structure, p is 0-7, q is 0-6, n is 0-3, and X− indicates a sulfonic acid anion. The positive-tone radiation-sensitive resin composition comprises (A) a photoacid generator of the sulfonium-salt compound and (B) an acid-dissociable group-containing resin.
摘要翻译：对于220nm以下的波长的紫外线的透明性优异的锍盐化合物，当用作光致酸产生剂，光致酸产生剂，具有良好平衡的优异性能，例如灵敏度，分辨率，图案形式，LER和储存稳定性包含锍盐化合物和含有光酸产生剂的正色散辐射敏感性树脂组合物。锍盐化合物由下式（I）表示，其中R 1表示卤素原子，烷基，一价脂环族烃基，烷氧基或-OR 3 其中R 3是一价脂环族烃基，R 2表示（取代的） - 烷基或两个或更多个R 2， / SUP>基团形成环状结构，p为0-7，q为0-6，n为0-3，X为 - 表示磺酸阴离子。正色辐射敏感性树脂组合物包含（A）锍盐化合物的光酸产生剂和（B）含酸解离基团的树脂。

6. 发明授权

US07399806B2 Synthesis of photoresist polymers 失效
标题翻译：光致抗蚀剂聚合物的合成
公开(公告)号：US07399806B2
公开(公告)日：2008-07-15
申请号：US11734474
申请日：2007-04-12
申请人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
发明人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
IPC分类号： C08F2/38 , C08F4/04
CPC分类号： C08F220/30 , C08F2/38 , C08F20/30 , C08F220/18 , C08F293/005 , G03F7/0046 , G03F7/0397
摘要： The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.
摘要翻译：本发明涉及通过活性自由基聚合技术制备光致抗蚀剂聚合物。用作单体体积大的酯单体作为聚合组分。链转移剂的使用包括在聚合工艺条件中。描述了包含杂原子的聚合物末端基团的切割。

7. 发明授权

US07517634B2 Photoresist polymers 有权
标题翻译：光致抗蚀剂聚合物
公开(公告)号：US07517634B2
公开(公告)日：2009-04-14
申请号：US11300658
申请日：2005-12-12
申请人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
发明人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
IPC分类号： G03F7/00 , G03F7/004
CPC分类号： C08F220/28 , C08F20/18 , G03F7/0397
摘要： The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.
摘要翻译：本发明涉及通过活性自由基聚合技术制备光致抗蚀剂聚合物。用作单体体积大的酯单体作为聚合组分。链转移剂的使用包括在聚合工艺条件中。描述了包含杂原子的聚合物末端基团的切割。

8. 发明申请

US20060257781A1 Photoresist polymer compositions 有权
公开(公告)号：US20060257781A1
公开(公告)日：2006-11-16
申请号：US11300657
申请日：2005-12-12
申请人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Isao Nishimura , Akimasa Soyano , Kenji Okamoto , Yong Wang
发明人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Isao Nishimura , Akimasa Soyano , Kenji Okamoto , Yong Wang
IPC分类号： G03C1/00
CPC分类号： C08F220/18 , C08F20/18 , C08F220/28 , G03F7/0397
摘要： The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.

9. 发明申请

US20060234154A1 Radiation-sensitive resin composition 有权
标题翻译：辐射敏感树脂组合物
公开(公告)号：US20060234154A1
公开(公告)日：2006-10-19
申请号：US10541032
申请日：2003-12-24
申请人： Isao Nishimura , Kouichi Fujiwara , Eiichi Kobayashi , Tsutomu Shimokawa , Atsushi Nakamura , Eiji Yoneda , Yong Wang
发明人： Isao Nishimura , Kouichi Fujiwara , Eiichi Kobayashi , Tsutomu Shimokawa , Atsushi Nakamura , Eiji Yoneda , Yong Wang
IPC分类号： G03C1/00
CPC分类号： G03F7/039 , G03F7/0046 , G03F7/0397 , G03F7/2006
摘要： A radiation-sensitive resin composition comprising an acid-labile group-containing resin obtained by living radical polymerization having a specific structure which is insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid, and a photoacid generator, wherein the ratio of weight average molecular weight to number average molecular weight (weight average molecular weight/number average molecular weight) of the acid-labile group-containing resin is smaller than 1.5.
摘要翻译：一种辐射敏感性树脂组合物，其包含通过活性自由基聚合而获得的含酸不稳定基团的树脂，其具有不溶于或几乎不溶于碱，但通过酸的作用而变得碱溶性的特定结构和光酸产生剂，其中重均分子量与含酸不稳定基团树脂的数均分子量（重均分子量/数均分子量）的比例小于1.5。

10. 发明申请

US20060122346A9 Synthesis of photoresist polymers 失效
标题翻译：光致抗蚀剂聚合物的合成
公开(公告)号：US20060122346A9
公开(公告)日：2006-06-08
申请号：US10877110
申请日：2004-06-25
申请人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
发明人： Didier Benoit , Adam Safir , Han-Ting Chang , Dominique Charmot , Kenji Okamoto , Isao Nishimura , Yong Wang
IPC分类号： C08F2/00
CPC分类号： C08F220/30 , C08F2/38 , C08F20/30 , C08F220/18 , C08F293/005 , G03F7/0046 , G03F7/0397
摘要： The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.
摘要翻译：本发明涉及通过活性自由基聚合技术制备光致抗蚀剂聚合物。用作单体体积大的酯单体作为聚合组分。链转移剂的使用包括在聚合工艺条件中。描述了包含杂原子的聚合物末端基团的切割。

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