公开(公告)号：US09040221B2

公开(公告)日：2015-05-26

申请号：US13699007

申请日：2011-05-19

申请人： Hitoshi Osaki ,  Yusuke Asano ,  Mitsuo Sato ,  Tomoki Nagai

发明人： Hitoshi Osaki ,  Yusuke Asano ,  Mitsuo Sato ,  Tomoki Nagai

IPC分类号： G03F7/004 ,  C08F22/18 ,  C08F220/26 ,  G03F7/038 ,  G03F7/039 ,  G03F7/20 ,  C07C69/653 ,  C07C69/753 ,  C07D307/93 ,  C08F24/00 ,  C08F220/24

CPC分类号： G03F7/004 ,  C07C69/653 ,  C07C69/753 ,  C07D307/93 ,  C08F22/18 ,  C08F24/00 ,  C08F220/24 ,  C08F220/26 ,  G03F7/0046 ,  G03F7/0382 ,  G03F7/0392 ,  G03F7/2041

摘要： A radiation-sensitive resin composition that provides a resist coating film in a liquid immersion lithography process is provided, the radiation-sensitive resin composition being capable of exhibiting a great dynamic contact angle during exposure, whereby the surface of the resist coating film can exhibit a superior water draining property, and the radiation-sensitive resin composition being capable of leading to a significant decrease in the dynamic contact angle during development, whereby generation of development defects can be inhibited, and further shortening of a time period required for change in a dynamic contact angle is enabled. A radiation-sensitive resin composition including (A) a fluorine-containing polymer having a structural unit (I) that includes a group represented by the following formula (1), and (B) a radiation-sensitive acid generator.

摘要翻译： 提供了一种在液浸光刻工艺中提供抗蚀剂涂膜的辐射敏感性树脂组合物，该曝光敏感性树脂组合物能够在曝光期间表现出很大的动态接触角，由此抗蚀剂涂膜的表面可呈现出 排水性优异，并且能够导致显影期间动态接触角显着降低的放射线敏感性树脂组合物，从而可以抑制显影缺陷的产生，并且进一步缩短动态变化所需的时间段 接触角启用。 一种辐射敏感性树脂组合物，其包含（A）具有由下式（1）表示的基团的结构单元（I）的含氟聚合物和（B）辐射敏感性酸发生剂。

公开(公告)号：US20130122426A1

公开(公告)日：2013-05-16

申请号：US13699007

申请日：2011-05-19

申请人： Hitoshi Osaki ,  Yusuke Asano ,  Mitsuo Sato ,  Tomoki Nagai

发明人： Hitoshi Osaki ,  Yusuke Asano ,  Mitsuo Sato ,  Tomoki Nagai

IPC分类号： G03F7/004 ,  C08F22/18 ,  G03F7/20 ,  C07C69/753 ,  C08F24/00 ,  C07C69/653 ,  C07D307/93

CPC分类号： G03F7/004 ,  C07C69/653 ,  C07C69/753 ,  C07D307/93 ,  C08F22/18 ,  C08F24/00 ,  C08F220/24 ,  C08F220/26 ,  G03F7/0046 ,  G03F7/0382 ,  G03F7/0392 ,  G03F7/2041

摘要： A radiation-sensitive resin composition that provides a resist coating film in a liquid immersion lithography process is provided, the radiation-sensitive resin composition being capable of exhibiting a great dynamic contact angle during exposure, whereby the surface of the resist coating film can exhibit a superior water draining property, and the radiation-sensitive resin composition being capable of leading to a significant decrease in the dynamic contact angle during development, whereby generation of development defects can be inhibited, and further shortening of a time period required for change in a dynamic contact angle is enabled. A radiation-sensitive resin composition including (A) a fluorine-containing polymer having a structural unit (I) that includes a group represented by the following formula (1), and (B) a radiation-sensitive acid generator.

摘要翻译： 提供了一种在液浸光刻工艺中提供抗蚀剂涂膜的辐射敏感性树脂组合物，该曝光敏感性树脂组合物能够在曝光期间表现出很大的动态接触角，由此抗蚀剂涂膜的表面可呈现出 排水性优异，并且能够导致显影期间动态接触角显着降低的放射线敏感性树脂组合物，从而可以抑制显影缺陷的产生，并且进一步缩短动态变化所需的时间段 接触角启用。 一种辐射敏感性树脂组合物，其包含（A）具有由下式（1）表示的基团的结构单元（I）的含氟聚合物和（B）辐射敏感性酸发生剂。

公开(公告)号：US20090318652A1

公开(公告)日：2009-12-24

申请号：US12097414

申请日：2006-12-13

申请人： Tomoki Nagai ,  Takuma Ebata ,  Nobuji Matsumura

发明人： Tomoki Nagai ,  Takuma Ebata ,  Nobuji Matsumura

IPC分类号： C08F28/02 ,  C07C69/533

CPC分类号： G03F7/0045 ,  C07C309/06 ,  C07C309/19 ,  C07C381/12 ,  C07C2602/42 ,  C08F220/38 ,  G03F7/0397

摘要： A radiation-sensitive resin composition which has high transparency to radiation, excelling in basic properties as a resist such as sensitivity, resolution, and pattern shape, and, in particular, exhibiting high resolution performance, excellent DOF and LER, and high resistance to a liquid medium used in liquid immersion lithography is provided. Also provided are a polymer which can be used in the composition, a novel compound useful for synthesizing the polymer, and a method of producing the composition. A radiation-sensitive resin composition having an excellent resistance to a liquid medium can be obtained by using the novel compound shown by the following formula (1), wherein R1 represents a methyl group or a hydrogen atom, R2, R3 and R4 individually represent a substituted or unsubstituted monovalent organic group having 1 to 10 carbon atoms, n is an integer from 0 to 3, A represents a methylene group, a linear or branched alkylene group having 2 to 10 carbon atoms, or an arylene group, and X− represents a counter ion of S+.

摘要翻译： 对辐射具有高透明度的辐射敏感性树脂组合物，作为抗敏剂如感光度，分辨率和图案形状的基本性能优异，特别是表现出高分辨率性能，优异的DOF和LER，以及对 提供了用于液浸光刻的液体介质。 还提供了可用于组合物中的聚合物，可用于合成聚合物的新化合物，以及该组合物的制备方法。 通过使用由下式（1）表示的新化合物，其中R 1表示甲基或氢原子，可以得到对液体介质具有优异抗性的辐射敏感性树脂组合物，R2，R3和R4分别表示 取代或未取代的碳原子数1〜10的一价有机基团，n表示0〜3的整数，A表示亚甲基，碳原子数2〜10的直链或支链亚烷基或亚芳基，X表示 S +的反离子。

公开(公告)号：US07258962B2

公开(公告)日：2007-08-21

申请号：US11117344

申请日：2005-04-29

申请人： Tomoki Nagai ,  Takayuki Tsuji

发明人： Tomoki Nagai ,  Takayuki Tsuji

IPC分类号： G03F7/004 ,  G03F7/30

CPC分类号： G03F7/0045 ,  G03F7/0392 ,  Y10S430/106 ,  Y10S430/115 ,  Y10S430/121 ,  Y10S430/127

摘要： A positive-tone radiation-sensitive resin composition comprising: (A) a carbazole derivative shown by the following formula (1), (B) a photoacid generator containing a sulfonimide compound and an iodonium salt compound as essential components, and (C) an acid-dissociable group-containing resin which is insoluble or scarcely soluble in alkali, but becomes soluble in alkali when the acid-dissociable group dissociates is disclosed. wherein R1 and R2 are individually halogen atom, methyl, cyano, or nitro group, X is a C1-20 organic group, and h and i are 0-4. The resin composition is useful as a chemically amplified positive-tone resist excelling in focal depth allowance, sensitivity, resolution, pattern profile, and PED stability.

摘要翻译： 1.一种正色射线敏感性树脂组合物，其含有：（A）下述式（1）表示的咔唑衍生物，（B）含有磺酰亚胺化合物和碘鎓盐化合物作为必要成分的光酸产生剂，（C） 公开了酸解离基团的树脂，其不溶于或几乎不溶于碱，但在酸解离基解离时变得可溶于碱。 其中R 1和R 2各自为卤素原子，甲基，氰基或硝基，X为C 1-20官能团， 而h和i为0-4。 该树脂组合物可用作具有优异的焦深度余量，灵敏度，分辨率，图案分布和PED稳定性的化学放大正色调抗蚀剂。

公开(公告)号：US20050244747A1

公开(公告)日：2005-11-03

申请号：US11117344

申请日：2005-04-29

申请人： Tomoki Nagai ,  Takayuki Tsuji

发明人： Tomoki Nagai ,  Takayuki Tsuji

IPC分类号： G03F7/004 ,  G03C1/492 ,  G03F7/039 ,  G03F7/20 ,  H01L21/027

CPC分类号： G03F7/0045 ,  G03F7/0392 ,  Y10S430/106 ,  Y10S430/115 ,  Y10S430/121 ,  Y10S430/127

摘要： A positive-tone radiation-sensitive resin composition comprising: (A) a carbazole derivative shown by the following formula (1), (B) a photoacid generator containing a sulfonimide compound and an iodonium salt compound as essential components, and (C) an acid-dissociable group-containing resin which is insoluble or scarcely soluble in alkali, but becomes soluble in alkali when the acid-dissociable group dissociates is disclosed. wherein R1 and R2 are individually halogen atom, methyl, cyano, or nitro group, X is a C1-20 organic group, and h and i are 0-4. The resin composition is useful as a chemically amplified positive-tone resist excelling in focal depth allowance, sensitivity, resolution, pattern profile, and PED stability.

摘要翻译： 1.一种正色射线敏感性树脂组合物，其含有：（A）下述式（1）表示的咔唑衍生物，（B）含有磺酰亚胺化合物和碘鎓盐化合物作为必要成分的光酸产生剂，（C） 公开了酸解离基团的树脂，其不溶于或几乎不溶于碱，但在酸解离基解离时变得可溶于碱。 其中R 1和R 2各自为卤素原子，甲基，氰基或硝基，X为C 1-20官能团， 而h和i为0-4。 该树脂组合物可用作具有优异的焦深度余量，灵敏度，分辨率，图案分布和PED稳定性的化学放大正色调抗蚀剂。

公开(公告)号：US08808446B2

公开(公告)日：2014-08-19

申请号：US11816642

申请日：2006-02-24

申请人： Keiji Konno ,  Masato Tanaka ,  Momoko Ishii ,  Junichi Takahashi ,  Tomoki Nagai

发明人： Keiji Konno ,  Masato Tanaka ,  Momoko Ishii ,  Junichi Takahashi ,  Tomoki Nagai

IPC分类号： C09D4/00 ,  G03F7/075 ,  C07F7/08 ,  H01L21/027 ,  G03F7/11 ,  H01L21/033

CPC分类号： G03F7/0752 ,  G03F7/0751 ,  G03F7/11 ,  H01L21/0274 ,  H01L21/0332 ,  Y10S430/106 ,  Y10S430/115 ,  Y10T428/31515 ,  Y10T428/31612 ,  Y10T428/31663

摘要： A composition for a resist underlayer film is provided. The composition has excellent storage stability and can form a resist underlayer film which has excellent adhesion to a resist film, can improve reproducibility of a resist pattern and is resistant to an alkaline liquid used in development and to oxygen ashing during the removal of a resist. The composition comprises a hydrolyzate and/or a condensate of a silane compound of the following formula (A), R1bR2cSi(OR3)4-a  (A) wherein R1 is a monovalent organic group having at least one unsaturated bond, R2 individually represents a hydrogen atom, a halogen atom or a monovalent organic group, R3 individually represents a monovalent organic group, R1 is a group other than OR3, a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 0 to 2, provided that a=b+c.

摘要翻译： 提供了抗蚀剂下层膜用组合物。 该组合物具有优异的储存稳定性，并且可以形成对抗蚀剂膜具有优异粘附性的抗蚀剂下层膜，可以提高抗蚀剂图案的再现性，并且耐除去抗蚀剂期间用于显影的碱性液体和氧气灰化。 该组合物包含下式（A）的硅烷化合物的水解产物和/或缩合物，其中R1是具有至少一个不饱和键的一价有机基团的R 1 b R 2 c Si（OR 3）4-a（A），R 2各自表示 氢原子，卤原子或一价有机基团，R 3分别表示一价有机基团，R 1为除OR 3以外的基团，a为1〜3的整数，b为1〜3的整数，c为 0〜2的整数，条件是a = b + c。

公开(公告)号：US20120244478A1

公开(公告)日：2012-09-27

申请号：US13489683

申请日：2012-06-06

申请人： Atsushi Nakamura ,  Tomoki Nagai ,  Takayoshi Abe ,  Tomohiro Kakizawa

发明人： Atsushi Nakamura ,  Tomoki Nagai ,  Takayoshi Abe ,  Tomohiro Kakizawa

IPC分类号： G03F7/20

CPC分类号： G03F7/70466 ,  G03F7/0035 ,  G03F7/0392 ,  G03F7/40 ,  H01L21/0274

摘要： A resist pattern formation method includes providing a first positive-tone radiation-sensitive resin composition on a substrate to form a first resist layer. The first resist layer is selectively exposed and developed to form a first resist pattern. The first resist pattern is coated with a resist pattern insolubilizing resin composition which comprises a resin and an alcohol solvent, the resin having a hydroxyl group. The resist pattern insolubilizing resin composition is baked or cured with UV to insolubilize the first resist pattern in a developer and in a second positive-tone radiation-sensitive resin composition. The resist pattern insolubilizing resin composition is developed to form an insolubilized resist pattern. The second positive-tone radiation-sensitive resin composition is provided on the insolubilized resist pattern to form a second resist layer. The second resist layer is selectively exposed and developed to form a second resist pattern.

摘要翻译： 抗蚀剂图案形成方法包括在基板上提供第一正色散辐射敏感树脂组合物以形成第一抗蚀剂层。 第一抗蚀剂层被选择性地曝光和显影以形成第一抗蚀剂图案。 第一抗蚀剂图案涂覆有抗蚀剂图案不溶化树脂组合物，其包含树脂和醇溶剂，该树脂具有羟基。 抗蚀剂图案不溶化树脂组合物用UV烘烤或固化，以使显影剂中的第一抗蚀图案和第二正色辐射敏感树脂组合物不溶化。 抗蚀剂图案不溶化树脂组合物被显影以形成不溶的抗蚀剂图案。 在不溶解的抗蚀剂图案上设置第二正色辐射敏感性树脂组合物以形成第二抗蚀剂层。 第二抗蚀剂层被选择性地曝光和显影以形成第二抗蚀剂图案。

公开(公告)号：US07335457B2

公开(公告)日：2008-02-26

申请号：US11235101

申请日：2005-09-27

申请人： Daisuke Shimizu ,  Tomoki Nagai ,  Yuuji Yada ,  Kentarou Gotou

发明人： Daisuke Shimizu ,  Tomoki Nagai ,  Yuuji Yada ,  Kentarou Gotou

IPC分类号： G03F7/004

CPC分类号： G03F7/0045 ,  G03F7/0392 ,  G03F7/091 ,  Y10S430/106 ,  Y10S430/111 ,  Y10S430/127

摘要： A positive-tone radiation-sensitive resin composition containing an anthracene-based carboxylic acid component with low sublimation properties and excellent compatibility with other components is provided. The composition exhibits optimum controllability of radiation transmittance as a chemically amplified positive-tone resist effectively responding to active radiation, particularly to deep ultraviolet rays, effectively controlling line width variation in resist patterns due to fluctuation in the resist film thickness on a highly refractive substrate, and exhibiting excellent focal depth allowance.The composition comprises (A) an anthracene derivative of the following formula (1), (B) a photoacid generator comprising a sulfonimide compound, and, (C) a resin containing an acid-dissociable group, wherein R1 is a hydrogen atom or a monovalent organic group, R2 is a monovalent organic group, e is an integer of 0-3, and f is an integer of 0-8. The metal impurity content in the component (A), in terms of the total ion content, is preferably 5,000 ppb or less.

摘要翻译： 提供了含有具有低升华性和与其它成分的良好相容性的蒽类羧酸成分的正色散辐射敏感性树脂组合物。 该组合物作为化学扩增的正色调抗蚀剂具有最佳的辐射透射性可控性，其有效地响应于有源辐射，特别是对深紫外线，有效地控制由于高折射性基底上的抗蚀剂膜厚度的波动导致的抗蚀剂图案的线宽度变化， 并表现出优异的焦深度补偿。 该组合物包含（A）下式（1）的蒽衍生物，（B）包含磺酰亚胺化合物的光酸产生剂，和（C）含有酸解离基团的树脂，其中R 1， SUP>是氢原子或一价有机基团，R 2是一价有机基团，e是0-3的整数，f是0-8的整数。 组分（A）中的金属杂质含量相对于总离子含量优选为5,000ppb以下。

公开(公告)号：US07105269B2

公开(公告)日：2006-09-12

申请号：US10321518

申请日：2002-12-18

申请人： Tomoki Nagai ,  Daisuke Shimizu ,  Tsutomu Shimokawa ,  Fumihisa Miyajima ,  Masaaki Miyaji

发明人： Tomoki Nagai ,  Daisuke Shimizu ,  Tsutomu Shimokawa ,  Fumihisa Miyajima ,  Masaaki Miyaji

IPC分类号： C03F7/004 ,  C08L29/00 ,  C08F232/00

CPC分类号： C08F212/14 ,  C08F220/18 ,  G03F7/0397 ,  Y10S430/106 ,  Y10S430/111

摘要： 1. A copolymer having recurring units of the following formulas (1), (2), and (3), wherein R1, R4, R5, and R6 are a hydrogen atom or a methyl group, R2, R3, and R7 represent a monovalent organic group, k is 1 or 2, 1 is 0–4, n is 1–3, m is 0–3, R8 is a substituted methyl group, 1-substituted ethyl group, 1-branched alkyl group, triorganosilyl group, triorganogermyl group, alkoxycarbonyl group, acyl group, or cyclic acid-dissociable group, with two or more R8 groups being the same or different, q is 1–3, and p is 0–3, the copolymer having a GPC average molecular weight of 3,000–100,000. The composition is useful as a polymer component for a radiation-sensitive resin composition suitable as a chemically-amplified resist.

摘要翻译： 1.具有下式（1），（2）和（3）的重复单元的共聚物，其中R 1，R 4，R 5 R 6和R 6是氢原子或甲基，R 2，R 3和R 7 表示一价有机基团，k为1或2，1为0-4，n为1-3，m为0-3，R 8为取代甲基，1 取代乙基，1-支链烷基，三有机甲硅烷基，三有机甲基，烷氧基羰基，酰基或环状酸解离基，其中两个或多个R 8基团相同或不同， q为1-3，p为0-3，GPC的平均分子量为3,000〜100,000。 该组合物可用作适合作为化学增幅抗蚀剂的辐射敏感性树脂组合物的聚合物组分。

公开(公告)号：US20050095527A1

公开(公告)日：2005-05-05

申请号：US10679367

申请日：2003-10-07

申请人： Kenichi Yokoyama ,  Fumihisa Miyajima ,  Tomoki Nagai ,  Eiji Yoneda

发明人： Kenichi Yokoyama ,  Fumihisa Miyajima ,  Tomoki Nagai ,  Eiji Yoneda

IPC分类号： G03F7/004 ,  G03C1/76 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0382 ,  G03F7/0392 ,  Y10S430/106 ,  Y10S430/111 ,  Y10S430/115 ,  Y10S430/12 ,  Y10S430/122

摘要： A positive tone radiation-sensitive resin composition comprising (A) a 1-substituted imidazole, (B) a photoacid generator, and (C-a) a resin protected by an acid-dissociable group, insoluble or scarcely soluble in alkali, but becoming soluble in alkali when the acid-dissociable group dissociates or (C-b) an alkali-soluble resin and an alkali solubility controller, and a negative tone radiation-sensitive resin composition comprising (A), (B), (D) an alkali-soluble resin, and (E) a compound that can crosslink the alkali-soluble resin in the presence of an acid. The radiation-sensitive resin composition of the present invention is a chemically amplified resist exhibiting high resolution and high storage stability as a composition, and suitable for microfabrication sensible to active radiations, for example, ultraviolet rays such as g-lines and i-lines, deep ultraviolet rays represented by a KrF excimer laser, ArF excimer laser, F2 excimer laser, and EUV excimer laser, and electron beams.

摘要翻译： 一种正色散辐射敏感性树脂组合物，其包含（A）1-取代咪唑，（B）光酸产生剂和（Ca）由酸解离基团保护的树脂，其不溶或几乎不溶于碱，但可溶于 （Cb）碱溶性树脂和碱溶性控制剂，以及包含（A），（B），（D）碱溶性树脂的负色调辐射敏感性树脂组合物， 和（E）可在酸存在下使碱溶性树脂交联的化合物。 本发明的放射线敏感性树脂组合物是作为组合物具有高分辨率和高储存稳定性的化学放大型抗蚀剂，适用于对活性辐射敏感的微细加工，例如，γ-线和i线等紫外线， 由KrF准分子激光器，ArF准分子激光器，F 2激子和EUV准分子激光器表示的深紫外线以及电子束。