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31. 发明授权

US08574817B2 Positive resist composition and patterning process 有权
标题翻译：正抗蚀剂组成和图案化工艺
公开(公告)号：US08574817B2
公开(公告)日：2013-11-05
申请号：US13613939
申请日：2012-09-13
申请人： Jun Hatakeyama , Koji Hasegawa
发明人： Jun Hatakeyama , Koji Hasegawa
IPC分类号： G03F7/039 , G03F7/20 , G03F7/30
CPC分类号： C08F220/30 , G03F7/0045 , G03F7/0046 , G03F7/0392
摘要： A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.
摘要翻译：包含具有由具有式（1），（2）或（3）的酸不稳定基取代的羧基的聚合物的正型抗蚀剂组合物在曝光前后表现出高对比度的碱溶解速率，高分辨率，降低的酸扩散并且形成具有良好外形，最小边缘粗糙度和耐蚀刻性的图案。在式（1）中，R 1，R 2，R 5，R 6，R 8和R 9为烷基，芳基或烯基，R 3，R 4，R 7，R 10和R 11为氢，烷基，烷氧基，酰氧基，卤素，，羟基或三氟甲基，M是亚甲基或亚乙基，R是单键或连接基团。

32. 发明申请

US20130084528A1 POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS 有权
标题翻译：积极的组合和绘图过程
公开(公告)号：US20130084528A1
公开(公告)日：2013-04-04
申请号：US13599398
申请日：2012-08-30
申请人： Jun Hatakeyama , Koji Hasegawa
发明人： Jun Hatakeyama , Koji Hasegawa
IPC分类号： C08F220/68 , G03F7/004 , C08F228/06 , C08F232/08 , C08F234/02 , C08F228/04 , G03F7/20
CPC分类号： C08F220/68 , C08F220/22 , C08F228/04 , C08F228/06 , C08F232/08 , C08F234/02 , G03F7/0045 , G03F7/0046 , G03F7/0392 , G03F7/0397 , Y10S430/111
摘要： A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1 is methylene or ethylene, R2 is alkyl, aryl, or alkenyl, which may contain oxygen or sulfur, R3 is fluorine or trifluoromethyl, and m is an integer of 1 to 4.
摘要翻译：包含具有由具有式（1）的酸不稳定基团取代的羧基的聚合物的正型抗蚀剂组合物在曝光前后显示出高的对比度的碱溶解速率，高分辨率，降低的酸扩散速率，并形成良好的图案轮廓，最小边缘粗糙度和耐蚀刻性。在式（1）中，R 1是亚甲基或亚乙基，R 2是可以含有氧或硫的烷基，芳基或烯基，R 3是氟或三氟甲基，m是1至4的整数。

33. 发明申请

US20120135349A1 POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS 有权
标题翻译：积极的组合和绘图过程
公开(公告)号：US20120135349A1
公开(公告)日：2012-05-31
申请号：US13300894
申请日：2011-11-21
申请人： Jun Hatakeyama , Koji Hasegawa
发明人： Jun Hatakeyama , Koji Hasegawa
IPC分类号： G03F7/20 , C08F26/06 , C08F28/06 , G03F7/039
CPC分类号： G03F7/0392 , C08F220/18 , C08F2220/283 , C08F2220/346 , C08F2220/382 , G03F7/0045 , G03F7/0046 , G03F7/0397 , G03F7/085
摘要： A polymer obtained from copolymerization of a recurring unit having a carboxyl group and/or phenolic hydroxyl group substituted with an acid labile group with a methacrylate having a phenolic hydroxyl-bearing pyridine is useful as a base resin in a positive resist composition. The resist composition comprising the polymer is improved in contrast of alkali dissolution rate before and after exposure, acid diffusion control, resolution, and profile and edge roughness of a pattern after exposure.
摘要翻译：由具有酸不稳定基取代的具有羧基和/或酚羟基的重复单元与具有含酚羟基的吡啶的甲基丙烯酸酯共聚得到的聚合物可用作正性抗蚀剂组合物中的基础树脂。包含聚合物的抗蚀剂组合物在曝光前后的碱溶解速率，酸扩散控制，分辨率以及曝光后图案的轮廓和边缘粗糙度的对比度方面得到改善。

34. 发明申请

US20120009527A1 PATTERNING PROCESS 有权
标题翻译：绘图过程
公开(公告)号：US20120009527A1
公开(公告)日：2012-01-12
申请号：US13177297
申请日：2011-07-06
申请人： Jun Hatakeyama , Kazuhiro Katayama , Koji Hasegawa
发明人： Jun Hatakeyama , Kazuhiro Katayama , Koji Hasegawa
IPC分类号： G03F7/20
CPC分类号： G03F7/0397 , G03F7/2041
摘要： A pattern is formed by coating a resist composition comprising a polymer comprising recurring units having an acid labile group-substituted hydroxyl group and recurring units having an acid labile group-substituted carboxyl group, an acid generator, and an organic solvent onto a substrate, prebaking to form a resist film, exposing the resist film to high-energy radiation, PEB, and developing the exposed film two times with an organic solvent and an alkaline aqueous solution. Due to the two developments, one line is divided into two lines, achieving a resolution doubling the mask pattern.
摘要翻译：通过将包含含有酸不稳定基取代的羟基的重复单元的聚合物和具有酸不稳定基取代的羧基的重复单元，酸产生剂和有机溶剂的抗蚀剂组合物涂布在基材上，预烘烤形成抗蚀剂膜，将抗蚀剂膜暴露于高能量辐射，PEB，并用有机溶剂和碱性水溶液将曝光的膜显影两次。由于两个发展，一条线分为两条线，实现了掩模图案加倍的分辨率。

35. 发明申请

US20110294070A1 MONOMER, POLYMER, CHEMICALLY AMPLIFIED POSITIVE RESIST COMPOSITION, AND PATTERNING PROCESS 有权
标题翻译：单体，聚合物，化学反应活性组分和方法
公开(公告)号：US20110294070A1
公开(公告)日：2011-12-01
申请号：US13150698
申请日：2011-06-01
申请人： Jun Hatakeyama , Seiichiro Tachibana , Koji Hasegawa
发明人： Jun Hatakeyama , Seiichiro Tachibana , Koji Hasegawa
IPC分类号： G03F7/004 , C08F214/18 , C07C69/54 , C08F220/68 , C08F224/00 , G03F7/20
CPC分类号： C08F214/18 , C07C69/54 , C07C69/96 , C07C2601/08 , C07C2601/14 , C07C2603/74 , C08F20/26 , G03F7/0045 , G03F7/0392 , G03F7/0395 , G03F7/0397 , Y10S430/111
摘要： A polymer is obtained from a hydroxyphenyl methacrylate monomer having an acid labile group substituted thereon. A positive resist composition comprising the polymer as a base resin has a very high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good profile and minimal line edge roughness of a pattern after exposure, a retarded acid diffusion rate, and good etching resistance.
摘要翻译：从其上取代酸不稳定基团的羟基苯基甲基丙烯酸酯单体获得聚合物。包含聚合物作为基础树脂的正型抗蚀剂组合物在曝光前后具有非常高的对比度的碱溶解速率，高分辨率，良好的轮廓和曝光后图案的最小线边缘粗糙度，延迟的酸扩散速率和耐腐蚀性好。

36. 发明授权

US07378548B2 Tertiary amine compounds having an ester structure and processes for preparing the same 有权
标题翻译：具有酯结构的叔胺化合物及其制备方法
公开(公告)号：US07378548B2
公开(公告)日：2008-05-27
申请号：US11423524
申请日：2006-06-12
申请人： Takeru Watanabe , Koji Hasegawa , Takeshi Kinsho , Jun Hatakeyama
发明人： Takeru Watanabe , Koji Hasegawa , Takeshi Kinsho , Jun Hatakeyama
IPC分类号： C07C205/00
CPC分类号： C07D307/33 , C07C229/12 , C07C229/16 , C07C2601/14 , C07D307/12 , C07D309/12 , C07D317/24 , G03F7/0045 , G03F7/0388 , G03F7/0392 , G03F7/0397
摘要： The present invention provides ester group-containing tertiary amine compounds of the formula (R1OCH2CH2)nN(CH2CH2CO2R2)3-n which, when used as additives in chemical amplification photolithography, can yield photoresists having a high resolution and an excellent focus margin. The present invention also provides a process comprising the step of subjecting a primary or secondary amine compound to Michael addition to an acrylic ester compound; a process comprising the steps of subjecting monoethanolamine or diethanolamine to Michael addition to an acrylic ester compound so as to form an ester group-containing amine compound and introducing a R1 group to the resultant ester group-containing amine compound; and a process comprising the step of effecting the ester exchange reaction of an ester group-containing tertiary amine with R2OH.
摘要翻译：本发明提供了式（R 1）2 OCH 2 CH 2 N酯的含酯基的叔胺化合物 > N（CH 2 CH 2）2 CO 2 N 2 - （CH 2）3 - n - 当用作化学放大光刻中的添加剂时，可以产生具有高分辨率和优异聚焦余量的光致抗蚀剂。本发明还提供了一种方法，其包括使伯胺或仲胺化合物与丙烯酸酯化合物进行迈克尔加成步骤; 一种方法包括以下步骤：将一乙醇胺或二乙醇胺加入到丙烯酸酯化合物中以形成含酯基的胺化合物并将R 1 O 2基团引入所得的含酯基胺复合; 以及包括使含酯基的叔胺与R 2 OH进行酯交换反应的步骤的方法。

37. 发明申请

US20060217570A1 Novel Tertiary Amine Compounds Having An Ester Structure And Processes For Preparing The Same 有权
标题翻译：具有酯结构的新型三元胺化合物及其制备方法
公开(公告)号：US20060217570A1
公开(公告)日：2006-09-28
申请号：US11423524
申请日：2006-06-12
申请人： Takeru Watanabe , Koji Hasegawa , Takeshi Kinsho , Jun Hatakeyama
发明人： Takeru Watanabe , Koji Hasegawa , Takeshi Kinsho , Jun Hatakeyama
IPC分类号： C07C229/22
CPC分类号： C07D307/33 , C07C229/12 , C07C229/16 , C07C2601/14 , C07D307/12 , C07D309/12 , C07D317/24 , G03F7/0045 , G03F7/0388 , G03F7/0392 , G03F7/0397
摘要： The present invention provides ester group-containing tertiary amine compounds of the formula (R1OCH2CH2)nN(CH2CH2CO2R2)3-n which, when used as additives in chemical amplification photolithography, can yield photoresists having a high resolution and an excellent focus margin. The present invention also provides a process comprising the step of subjecting a primary or secondary amine compound to Michael addition to an acrylic ester compound; a process comprising the steps of subjecting monoethanolamine or diethanolamine to Michael addition to an acrylic ester compound so as to form an ester group-containing amine compound and introducing a R1 group to the resultant ester group-containing amine compound; and a process comprising the step of effecting the ester exchange reaction of an ester group-containing tertiary amine with R2OH.
摘要翻译：本发明提供了式（R 1）2 OCH 2 CH 2 N酯的含酯基的叔胺化合物 > N（CH 2 CH 2）2 CO 2 N 2 - （CH 2）3 - n - 当用作化学放大光刻中的添加剂时，可以产生具有高分辨率和优异聚焦余量的光致抗蚀剂。本发明还提供了一种方法，其包括使伯胺或仲胺化合物与丙烯酸酯化合物进行迈克尔加成步骤; 一种方法包括以下步骤：将一乙醇胺或二乙醇胺加入到丙烯酸酯化合物中以形成含酯基的胺化合物并将R 1 O 2基团引入所得的含酯基胺复合; 以及包括使含酯基的叔胺与R 2 OH进行酯交换反应的步骤的方法。

38. 发明授权

US06667145B1 Resist composition and patterning process 有权
标题翻译：抗蚀剂组成和图案化工艺
公开(公告)号：US06667145B1
公开(公告)日：2003-12-23
申请号：US09694369
申请日：2000-10-24
申请人： Tsunehiro Nishi , Takeru Watanabe , Takeshi Kinsho , Koji Hasegawa , Tomohiro Kobayashi , Jun Hatakeyama
发明人： Tsunehiro Nishi , Takeru Watanabe , Takeshi Kinsho , Koji Hasegawa , Tomohiro Kobayashi , Jun Hatakeyama
IPC分类号： G03C173
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106
摘要： A resist composition contains as a base resin a polymer represented by the following formula and having a Mw of 1,000-500,000. R1 is H, methyl or CO2R2, R2 is alkyl, R3 is H, methyl or CH2CO2R2, at least one of R4 to R7 is a carboxyl or hydroxyl-containing monovalent hydrocarbon group, and the reminders are independently H or alkyl, at least one of R8 to R11 is a monovalent hydrocarbon group of 2 to 15 carbon atoms containing a —CO2— partial structure, and the reminders are independently H or alkyl, R12 is a polycyclic hydrocarbon group or an alkyl group containing such a polycyclic hydrocarbon group, R13 is an acid labile group, Z is a divalent group of atoms to construct a 5- or 6-membered ring which contains a carboxylate, carbonate or acid anhydride therein, k is 0 or 1, x is a number from more than 0 to 1, “a” to “d” are from 0 to less than 1, x+a+b+c+d=1. The resist composition has significantly improved resolution, substrate adhesiveness, and etching resistance and is very useful in precise microfabrication.
摘要翻译：抗蚀剂组合物包含作为基础树脂的由下式表示的聚合物，其Mw为1,000-500,000.R 1是H，甲基或CO 2 R 2，R 2是烷基，R 3是 H，甲基或CH 2 CO 2 R 2，R 4至R 7中的至少一个是含羧基或羟基的一价烃基，并且提醒独立地为H或烷基，R 8， R 11是含有-CO 2 - 部分结构的2至15个碳原子的一价烃基，并且提醒独立地是H或烷基，R 12是多环烃基或含有这种多环的烷基烃基，R 13是酸不稳定基团，Z是构成其中含有羧酸酯，碳酸酯或酸酐的5-或6-元环的二价原子基团，k是0或1，x是数字从0到1，“a”到“d”从0到小于1，x + a + b + c + d = 1。抗蚀剂组合物具有显着提高的分辨率，基底粘附性和耐蚀刻性，并且在精确微细加工中非常有用。

39. 发明授权

US06500971B2 Ester compounds having alicyclic and oxirane structures and method for preparing the same 有权
标题翻译：具有脂环和环氧乙烷结构的酯化合物及其制备方法
公开(公告)号：US06500971B2
公开(公告)日：2002-12-31
申请号：US09873193
申请日：2001-06-05
申请人： Takeru Watanabe , Takeshi Kinsho , Koji Hasegawa , Tsunehiro Nishi , Mutsuo Nakashima , Seiichiro Tachibana , Jun Hatakeyama
发明人： Takeru Watanabe , Takeshi Kinsho , Koji Hasegawa , Tsunehiro Nishi , Mutsuo Nakashima , Seiichiro Tachibana , Jun Hatakeyama
IPC分类号： C07D30316
CPC分类号： C08G65/22 , C07D303/48 , G03F7/0395
摘要： An ester compound of formula (1) is provided. R1 is H or methyl, R2 is tertiary C4-20 alkyl, and k=0 or 1. A resist composition comprising as the base resin a polymer resulting from the ester compound is sensitive to high-energy radiation, has excellent sensitivity, resolution, etching resistance and substrate adhesion, and is suited for micropatterning using electron beams or deep-UV.
摘要翻译：提供式（1）的酯化合物.R1是H或甲基，R2是叔C4-20烷基，k = 0或1.包含作为基础树脂的抗蚀剂组合物由酯化合物产生的聚合物敏感高能量辐射，具有优异的灵敏度，分辨率，耐蚀刻性和基板粘合性，适用于使用电子束或深紫外线的微图案。

40. 发明授权

US06492090B2 Polymers, resist compositions and patterning process 有权
标题翻译：聚合物，抗蚀剂组合物和图案化工艺
公开(公告)号：US06492090B2
公开(公告)日：2002-12-10
申请号：US09842113
申请日：2001-04-26
申请人： Tsunehiro Nishi , Seiichiro Tachibana , Mutsuo Nakashima , Takeshi Kinsho , Takeru Watanabe , Koji Hasegawa , Jun Hatakeyama
发明人： Tsunehiro Nishi , Seiichiro Tachibana , Mutsuo Nakashima , Takeshi Kinsho , Takeru Watanabe , Koji Hasegawa , Jun Hatakeyama
IPC分类号： G03F7038
CPC分类号： G03F7/039 , C08F222/06 , C08F222/40 , C08F232/08 , G03F7/0045 , C08F2220/1866 , C08F232/04 , C08F234/04 , C08F232/00
摘要： A polymer comprising units of formulas (1) and (2) and having a Mw of 1,000-500,000 is provided. R1 is H, CH3 or CH2CO2R3, R2 is H, CH3 or CO2R3, R3 is alkyl, R4 is H, alkyl, alkoxyalkyl or acyl, R5 is alkyl or aryl, Y is a divalent hydrocarbon group which may contain a hetero atom and which forms a ring with the carbon atom, Z is a trivalent hydrocarbon group, k is 0 or 1, and W is —O— or —(NR)— wherein R is H or alkyl. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation, has excellent sensitivity, resolution, and etching resistance, and lends itself to micropatterning with electron beams or deep-UV rays.
摘要翻译：提供了包含式（1）和（2）单元并且Mw为1,000-500,000的聚合物。 R1是H，CH3或CH2CO2R3，R2是H，CH3或CO2R3，R3是烷基，R4是H，烷基，烷氧基烷基或酰基，R5是烷基或芳基，Y是可以含有杂原子的二价烃基，与碳原子形成环，Z为三价烃基，k为0或1，W为-O-或 - （NR） - ，其中R为H或烷基。包含作为基础树脂的聚合物的抗蚀剂组合物对高能辐射敏感，具有优异的灵敏度，分辨率和耐蚀刻性，并且适用于电子束或深紫外线的微图案化。

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