公开(公告)号：US06927011B2

公开(公告)日：2005-08-09

申请号：US10332770

申请日：2001-02-09

申请人： Tadayuki Fujiwara ,  Yukiya Wakisaka ,  Toru Tokimitsu ,  Naoshi Murata ,  Yoshihiro Kamon ,  Hikaru Momose

发明人： Tadayuki Fujiwara ,  Yukiya Wakisaka ,  Toru Tokimitsu ,  Naoshi Murata ,  Yoshihiro Kamon ,  Hikaru Momose

IPC分类号： C08F20/28 ,  G03F7/039 ,  G03F7/038

CPC分类号： G03F7/0392 ,  C08F20/28 ,  Y10S430/106 ,  Y10S430/111

摘要： A resist resin containing a monomer unit selected from the group comprising a monomer unit represented by Formula (II): wherein a substituent R3 represents an alkyl group, or a functional group comprising an acid-deprotectable protecting group, m representing the number of R3 is 0 (non-substitution), 1, 2 or more, R3 may be different from each other, provided that m is 2 or more, and n represents an integer of 0 to 4, has no rough spots on the surface after etching and so has good dry etching resistance, and therefore the resist resin is preferably used as a photo resist for DUV.

摘要翻译： 含有选自由式（II）表示的单体单元的单体单元的抗蚀剂树脂：其中取代基R 3表示烷基，或包含酸可去保护的保护基的官能团 ，表示R 3的数目的m为0（非取代），1,2或更多个，R 3可以彼此不同，条件是m为2 以上，n表示0〜4的整数，蚀刻后的表面没有粗糙斑点，因此具有良好的耐干蚀刻性，因此抗蚀树脂优选用作DUV的光致抗蚀剂。

公开(公告)号：US20090198065A1

公开(公告)日：2009-08-06

申请号：US12411703

申请日：2009-03-26

申请人： Hikaru Momose ,  Atsushi Ootake ,  Tadashi Nakamura ,  Akifumi Ueda

发明人： Hikaru Momose ,  Atsushi Ootake ,  Tadashi Nakamura ,  Akifumi Ueda

IPC分类号： C07D211/00 ,  C07C69/608 ,  C07C69/74 ,  C07D307/02 ,  C07D309/02 ,  C07D311/78 ,  C07C323/00 ,  C07C69/96

CPC分类号： G03F7/0397 ,  C08F220/18 ,  C08F220/28 ,  C08F222/1006

摘要： To provide a resist polymer comprising, as a structural unit, an acid-decomposable unit having a structure represented by formula (1) or (2) which exhibits a small line edge roughness and produces little defects in DUV excimer laser lithography or the like. In formulas (1) and (2), n represents an integer of 2 to 24; J represents a single bond or a divalent hydrocarbon group which may have a substituent/heteroatom when n=2, or represents an n-valent hydrocarbon group which may have a substituent/heteroatom when n≧3; E represents a residue of a polymerization terminator, a chain transfer agent or a polymerization initiator; K1 and K2 each represent at least one selected from alkylene, cycloalkylene, oxyalkylene, arylene, a divalent thiazoline ring, a divalent oxazoline ring and a divalent imidazoline ring; L1 and L2 each represent at least one selected from —C(O)O—, —C(O)— and —OC(O)—; M1, M2 and M3 each represent at least one selected from alkylene, cycloalkylene, oxyalkylene and arylene; Y, Y1 and Y2 each represent an acid-decomposable linkage; k1, k2, l1, l2, m1, m2, and m3 each represent 0 or 1; and R1 represents H or a methyl group.

摘要翻译： 提供一种抗蚀剂聚合物，其包含作为结构单元的具有由式（1）或（2）表示的结构的酸可分解单元，其具有小的线边缘粗糙度，并且在DUV准分子激光光刻技术中几乎没有缺陷。 在式（1）和（2）中，n表示2〜24的整数， 当n = 2时，J表示单键或可以具有取代基/杂原子的二价烃基，或当n> = 3时，表示可以具有取代基/杂原子的n价烃基; E表示聚合终止剂，链转移剂或聚合引发剂的残基; K1和K2各自表示选自亚烷基，亚环烷基，氧化烯，亚芳基，二价噻唑啉环，二价恶唑啉环和二价咪唑啉环中的至少一种。 L1和L2各自表示选自-C（O）O - ， - C（O） - 和-OC（O） - 的至少一种; M1，M2和M3各自表示选自亚烷基，亚环烷基，氧化烯和亚芳基中的至少一种; Y，Y 1和Y 2各自表示酸分解键; k1，k2，l1，l2，m1，m2，m3各自表示0或1; R1表示H或甲基。

公开(公告)号：US07339014B2

公开(公告)日：2008-03-04

申请号：US10974876

申请日：2004-10-28

申请人： Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Hikaru Momose ,  Atsushi Koizumi

发明人： Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Hikaru Momose ,  Atsushi Koizumi

IPC分类号： C08F24/00 ,  C08F34/02

CPC分类号： G03F7/0397 ,  C07D307/88 ,  C07D307/93 ,  C08F220/18 ,  C08F220/28

摘要： A (meth)acrylate represented by the following formula (1): wherein each of R1, R2, R3 and R4 represents a hydrogen atom, a methyl group or an ethyl group; either one of X1 or X2 represents a (meth)acryloyloxy group and the other represents a hydrogen atom; both A1 and A2 represent hydrogen atoms, or A1 and A2 form —O—, —CH2— or —CH2CH2—, which can be produced by first producing a lactone by reducing an addition product obtained by the Diels-Alder reaction between 1,3-diene and maleic anhydride, and then hydrating the lactone to produce an alcohol followed by (meth)acrylation of the alcohol; a polymer produced by (co)polymerizing a monomer composition comprising the (meth)acrylate of the present invention is excellent in transparency, dry etching resistance, and solubility in organic solvents, and so it is preferably used as a resin for a chemically amplified resist composition.

摘要翻译： 由下式（1）表示的（甲基）丙烯酸酯：其中R 1，R 2，R 3和R 0中的每一个 > 4表示氢原子，甲基或乙基; X 1或X 2中的任一个表示（甲基）丙烯酰氧基，另一个表示氢原子; A 1和A 2都代表氢原子，或者A 1和A 2 O 2 - ， - O - CH 2 - 或-CH 2 CH 2 - ，其可以通过首先通过还原由Diels获得的加成产物来生产内酯来制备 - 1,3-二烯和马来酸酐之间的反应，然后水合内酯以产生醇，然后进行醇的（甲基）丙烯酸酯化; 通过（共）聚合本发明的（甲基）丙烯酸酯的单体组合物而制造的聚合物的透明性，耐干蚀刻性和在有机溶剂中的溶解性优异，因此优选用作化学增幅抗蚀剂的树脂 组成。

公开(公告)号：US07041838B2

公开(公告)日：2006-05-09

申请号：US10433570

申请日：2001-12-05

申请人： Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Hikaru Momose ,  Atsushi Koizumi

发明人： Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Hikaru Momose ,  Atsushi Koizumi

IPC分类号： C07D407/00

CPC分类号： G03F7/0397 ,  C07D307/88 ,  C07D307/93 ,  C08F220/18 ,  C08F220/28

摘要： A (meth)acrylate represented by the following formula (1): wherein each of R1, R2, R3 and R4 represents a hydrogen atom, a methyl group or an ethyl group; either one of X1 or X2 represents a (meth)acryloyloxy group and the other represents a hydrogen atom; both A1 and A2 represent hydrogen atoms, or A1 and A2 form —O—, —CH2— or —CH2CH2—, which can be produced by first producing a lactone by reducing an addition product obtained by the Diels-Alder reaction between 1,3-diene and maleic anhydride, and then hydrating the lactone to produce an alcohol followed by (meth)acrylation of the alcohol; a polymer produced by (co)polymerizing a monomer composition comprising the (meth)acrylate of the present invention is excellent in transparency, dry etching resistance, and solubility in organic solvents, and so it is preferably used as a resin for a chemically amplified resist composition.

摘要翻译： 由下式（1）表示的（甲基）丙烯酸酯：其中R 1，R 2，R 3和R 0中的每一个 > 4表示氢原子，甲基或乙基; X 1或X 2中的任一个表示（甲基）丙烯酰氧基，另一个表示氢原子; A 1和A 2都代表氢原子，或者A 1和A 2 O 2 - ， - O - CH 2 - 或-CH 2 CH 2 - ，其可以通过首先通过还原由Diels获得的加成产物来生产内酯来制备 - 1,3-二烯与马来酸酐之间的反应，然后水合内酯以产生醇，然后进行醇的（甲基）丙烯酸酯化; 通过（共）聚合本发明的（甲基）丙烯酸酯的单体组合物而制造的聚合物的透明性，耐干蚀刻性和在有机溶剂中的溶解性优异，因此优选用作化学增幅抗蚀剂的树脂 组成。

公开(公告)号：US09733564B2

公开(公告)日：2017-08-15

申请号：US13879737

申请日：2011-10-14

申请人： Atsushi Yasuda ,  Tomoya Oshikiri ,  Hikaru Momose

发明人： Atsushi Yasuda ,  Tomoya Oshikiri ,  Hikaru Momose

IPC分类号： G03F7/004 ,  G03F7/20 ,  C08F2/00 ,  G01N24/08 ,  C08F120/28 ,  C08F220/28 ,  G03F7/038 ,  G03F7/039 ,  C08F220/18 ,  C08F220/20

CPC分类号： G03F7/004 ,  C08F2/00 ,  C08F120/28 ,  C08F220/18 ,  C08F220/20 ,  C08F220/28 ,  C08F2220/283 ,  C08F2400/02 ,  G01N24/085 ,  G03F7/0382 ,  G03F7/0392 ,  G03F7/0397 ,  G03F7/20

摘要： A target variable analysis unit (11) calculates the triad fractions of monomer units in the composition of a known polymer sample from the copolymerization reactivity ratios of the monomer units to obtain a target variable. A waveform processing unit (12) processes NMR measurements, signals, etc. An explanatory variable analysis unit (13) obtains explanatory variables from the amount of chemical shift and signal strength in the NMR measurements of the known sample. A model generation unit (14) determines the regression equation of the regression model of the target variable and the explanatory variables by partial least squares regression, and obtains regression model coefficients. A sample analysis unit (15) uses the regression model to calculate the triad fractions for an unknown copolymer sample from the amount of chemical shift and signal strength in the NMR measurements of the unknown copolymer sample. By using a copolymer for lithography in which the total of the triad fractions obtained in this way is not more than 20 mole % in the copolymer, a resist composition with excellent solubility and sensitivity can be manufactured.

公开(公告)号：US08476401B2

公开(公告)日：2013-07-02

申请号：US11574860

申请日：2005-09-06

申请人： Hikaru Momose ,  Akifumi Ueda

发明人： Hikaru Momose ,  Akifumi Ueda

IPC分类号： C08G63/08

CPC分类号： G03F7/004 ,  C08F220/28 ,  C08F222/20 ,  G03F7/0046 ,  G03F7/0397 ,  G03F7/2041 ,  G03F7/30

摘要： A resist polymer (Y′), which is used as a resist resin in DUV excimer laser lithography, electron beam lithography, and the like, contains a polymer (Y) comprising: a constituent unit (A) having a lactone skeleton; a constituent unit (B) having an acid-eliminable group; a constituent unit (C) having a hydrophilic group; and a constituent unit (E) having a structure represented by the following formula (1), wherein a content of the constituent unit (E) is 0.3 mol % or more based on the total number of the constituent units of the resist polymer (Y′): in the formula (1), L is a divalent linear, branched, or cyclic C1-20 hydrocarbon group which may have a substituent and/or a heteroatom; R11 is a g-valent linear, branched, or cyclic C1-20 hydrocarbon group which may have a substituent and/or a heteroatom; and g represents an integer of 1 to 24.

摘要翻译： 在DUV准分子激光光刻法，电子束光刻法等中用作抗蚀剂树脂的抗蚀剂聚合物（Y'）含有聚合物（Y），其包含：具有内酯骨架的构成单元（A） 具有酸可消除基团的构成单元（B） 具有亲水基团的构成单元（C） 和具有下述式（1）所示结构的构成单元（E），其中，构成单元（E）的含量相对于抗蚀剂聚合物（Y）的构成单位的总数为0.3摩尔％以上 '）：在式（1）中，L是可以具有取代基和/或杂原子的二价直链，支链或环状C 1-20烃基; R11是可以具有取代基和/或杂原子的g价直链，支链或环状C 1-20烃基; g表示1〜24的整数。

公开(公告)号：US07575846B2

公开(公告)日：2009-08-18

申请号：US10543914

申请日：2004-01-29

申请人： Hikaru Momose ,  Atsushi Ootake ,  Akifumi Ueda ,  Tadayuki Fujiwara ,  Masaru Takeshita ,  Ryotaro Hayashi ,  Takeshi Iwai

发明人： Hikaru Momose ,  Atsushi Ootake ,  Akifumi Ueda ,  Tadayuki Fujiwara ,  Masaru Takeshita ,  Ryotaro Hayashi ,  Takeshi Iwai

IPC分类号： G03C1/73 ,  G03F7/039 ,  C08F120/70 ,  C08F24/00

CPC分类号： C08F220/28 ,  G03F7/0397 ,  Y10S430/111

摘要： The resist polymer of the present invention comprises a specific constitutional unit having a cyano group, a constitutional unit having an acid-dissociable group, and a specific constitutional unit having a lactone skeleton. When the above polymer is used as a resist resin in DUV excimer laser lithography or electron beam lithography, it exhibits high sensitivity and high resolution, and provides a good resist pattern shape, having a small degree of occurrence of line edge roughness or generation of microgels.

摘要翻译： 本发明的抗蚀剂聚合物包含具有氰基的特定结构单元，具有酸解离基的结构单元和具有内酯骨架的特定结构单元。 当在DUV准分子激光光刻或电子束光刻中使用上述聚合物作为抗蚀剂树脂时，其表现出高灵敏度和高分辨率，并且提供良好的抗蚀剂图案形状，线边缘粗糙度的发生程度小或微凝胶的产生 。

公开(公告)号：US20080032241A1

公开(公告)日：2008-02-07

申请号：US11574860

申请日：2005-09-06

申请人： Hikaru Momose ,  Akifumi Ueda

发明人： Hikaru Momose ,  Akifumi Ueda

IPC分类号： C08G63/08 ,  G03C1/73

CPC分类号： G03F7/004 ,  C08F220/28 ,  C08F222/20 ,  G03F7/0046 ,  G03F7/0397 ,  G03F7/2041 ,  G03F7/30

摘要： A resist polymer (Y′), which is used as a resist resin in DUV excimer laser lithography, electron beam lithography, and the like, contains a polymer (Y) comprising: a constituent unit (A) having a lactone skeleton; a constituent unit (B) having an acid-eliminable group; a constituent unit (C) having a hydrophilic group; and a constituent unit (E) having a structure represented by the following formula (1), wherein a content of the constituent unit (E) is 0.3 mol % or more based on the total number of the constituent units of the resist polymer (Y′): [Chemical formula 1]in the formula (1), L is a divalent linear, branched, or cyclic C1-20 hydrocarbon group which may have a substituent and/or a heteroatom; R11 is a g-valent linear, branched, or cyclic C 120 hydrocarbon group which may have a substituent and/or a heteroatom; and g represents an integer of 1 to 24.

摘要翻译： 在DUV准分子激光光刻法，电子束光刻法等中用作抗蚀剂树脂的抗蚀剂聚合物（Y'）含有聚合物（Y），其包含：具有内酯骨架的构成单元（A） 具有酸可消除基团的构成单元（B） 具有亲水基团的构成单元（C） 和具有由下式（1）表示的结构的构成单元（E），其中，构成单元（E）的含量相对于抗蚀剂聚合物（Y）的构成单位的总数为0.3摩尔％以上 '）：式（1）中的[化学式1]，L是可以具有取代基和/或杂原子的二价直链，支链或环状C 1-20烃基; R 11是可以具有取代基和/或杂原子的g价线性，支链或环状C 120烃基; g表示1〜24的整数。

公开(公告)号：US07316884B2

公开(公告)日：2008-01-08

申请号：US10492207

申请日：2002-10-22

申请人： Ryuichi Ansai ,  Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Atsushi Ootake ,  Hikaru Momose

发明人： Ryuichi Ansai ,  Yoshihiro Kamon ,  Tadayuki Fujiwara ,  Hideaki Kuwano ,  Atsushi Ootake ,  Hikaru Momose

IPC分类号： G03C1/73 ,  G03F7/20 ,  G03F7/30 ,  C08F220/10 ,  C08F224/00 ,  C07D317/34 ,  C07D317/72

CPC分类号： C07D317/72 ,  C07D317/18 ,  C07D317/34 ,  C07D317/42 ,  C08F20/30 ,  C08F24/00 ,  G03F7/0392 ,  G03F7/0397 ,  Y10S430/106 ,  Y10S430/111 ,  Y10S430/143

摘要： A 5-methylene-1,3-dioxolan-4-one derivative and a monomer and copolymer thereof and a resist composition containing the polymer or copolymer where the 5-methylene-1,3 -dioxolan-4-one derivative is of formula (1): wherein R1 represents a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms, or a linear or branched alkyl group containing 1 to 6 carbon atoms which has a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms as a substituent; R2 represents a hydrogen atom, or a linear or branched alkyl group containing 1 to 6 carbon atoms; or R1 and R2 represent a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms together with the carbon atom to which they are bound, provided that the alkyl group and the bridged cyclic hydrocarbon group may have at least one substituent selected from a group consisting of a linear or branched alkyl group containing 1 to 6 carbon atoms which may be optionally substituted, a hydroxy group, a carboxy group, an acyl group containing 2 to 6 carbon atoms, an alkoxy group containing 1 to 6 carbon atoms, and a carboxy group esterified with an alcohol containing 1 to 6 carbon atoms.

摘要翻译： 5-亚甲基-1,3-二氧戊环-4-酮衍生物及其单体和共聚物以及含有聚合物或共聚物的抗蚀剂组合物，其中5-亚甲基-1,3-二氧戊环-4-酮衍生物具有式（ 1）表示：其中R 1表示含有4至16个碳原子的桥连环烃基，或含有1至6个碳原子的直链或支链烷基，其具有含有4至16个 碳原子作为取代基; R 2表示氢原子或含有1至6个碳原子的直链或支链烷基; 或R 1和R 2代表含有4至16个碳原子的桥连环烃基以及它们所连接的碳原子，条件是烷基和 桥连环状烃基可以具有至少一个选自含有1-6个碳原子的直链或支链烷基的取代基，其可任选被取代，羟基，羧基，含有2-6个碳原子的酰基 原子，含有1至6个碳原子的烷氧基，以及与含有1至6个碳原子的醇酯化的羧基。

公开(公告)号：US20070190449A1

公开(公告)日：2007-08-16

申请号：US10592057

申请日：2005-03-08

申请人： Hikaru Momose ,  Atsushi Ootake ,  Tadashi Nakamura ,  Akifumi Ueda

发明人： Hikaru Momose ,  Atsushi Ootake ,  Tadashi Nakamura ,  Akifumi Ueda

IPC分类号： G03C1/00

CPC分类号： G03F7/0397 ,  C08F220/18 ,  C08F220/28 ,  C08F222/1006

摘要： To provide a resist polymer comprising, as a structural unit, an acid-decomposable unit having a structure represented by formula (1) or (2) which exhibits a small line edge roughness and produces little defects in DUV excimer laser lithography or the like. In formulas (1) and (2), n represents an integer of 2 to 24; J represents a single bond or a divalent hydrocarbon group which may have a substituent/heteroatom when n=2, or represents an n-valent hydrocarbon group which may have a substituent/heteroatom when n≧3; E represents a residue of a polymerization terminator, a chain transfer agent or a polymerization initiator; K1 and K2 each represent at least one selected from alkylene, cycloalkylene, oxyalkylene, arylene, a divalent thiazoline ring, a divalent oxazoline ring and a divalent imidazoline ring; L1 and L2 each represent at least one selected from —C(O)O—, —C(O)— and —OC(O)—; M1, M2 and M3 each represent at least one selected from alkylene, cycloalkylene, oxyalkylene and arylene; Y, Y1 and Y2 each represent an acid-decomposable linkage; k1, k2, l1, l2, m1, m2, m3 and n1 each represent 0 or 1; and R1 represents H or a methyl group.

摘要翻译： 提供一种抗蚀剂聚合物，其包含作为结构单元的具有由式（1）或（2）表示的结构的酸可分解单元，其具有小的线边缘粗糙度，并且在DUV准分子激光光刻技术中几乎没有缺陷。 在式（1）和（2）中，n表示2〜24的整数， 当n = 2时，J表示单键或可以具有取代基/杂原子的二价烃基，或当n> = 3时，表示可以具有取代基/杂原子的n价烃基; E表示聚合终止剂，链转移剂或聚合引发剂的残基; K 1和K 2各自表示选自亚烷基，亚环烷基，氧化烯，亚芳基，二价噻唑啉环，二价恶唑啉环和二价咪唑啉环中的至少一种。 L 1和L 2各自表示选自-C（O）O - ， - C（O） - 和-OC（O） - 的至少一种。 M 1，M 2和M 3各自表示选自亚烷基，亚环烷基，氧化烯和亚芳基中的至少一种; Y，Y 1和Y 2各自表示酸可分解键; k1，k2，l1，l2，m1，m2，m3和n1各自表示0或1; R 1表示H或甲基。