公开(公告)号：US08431323B2

公开(公告)日：2013-04-30

申请号：US12608556

申请日：2009-10-29

申请人： Takeru Watanabe ,  Satoshi Shinachi ,  Takeshi Kinsho ,  Koji Hasegawa ,  Yuji Harada ,  Jun Hatakeyama ,  Kazunori Maeda ,  Tomohiro Kobayashi

发明人： Takeru Watanabe ,  Satoshi Shinachi ,  Takeshi Kinsho ,  Koji Hasegawa ,  Yuji Harada ,  Jun Hatakeyama ,  Kazunori Maeda ,  Tomohiro Kobayashi

IPC分类号： G03F7/039 ,  G03F7/11 ,  G03F7/20 ,  G03F7/30 ,  G03F7/38

CPC分类号： G03F7/11 ,  C07D307/04 ,  C07D307/77 ,  C07D315/00 ,  C07D319/06 ,  C08F14/18 ,  G03F7/0045 ,  G03F7/0046 ,  G03F7/0397 ,  G03F7/2041 ,  C08F2/00

摘要： A fluorinated monomer of cyclic acetal structure has formula (1) wherein R is a C1-C20 alkyl group which may be substituted with halogen or separated by oxygen or carbonyl, and Z is a divalent organic group which forms a ring with alkylenoxy and contains a polymerizable unsaturated group. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water sliding property, lipophilicity, acid lability and hydrolyzability and is useful in formulating a protective coating composition and a resist composition.

公开(公告)号：US20090081588A1

公开(公告)日：2009-03-26

申请号：US12236359

申请日：2008-09-23

申请人： Jun Hatakeyama ,  Koji Hasegawa ,  Takeru Watanabe ,  Yuji Harada

发明人： Jun Hatakeyama ,  Koji Hasegawa ,  Takeru Watanabe ,  Yuji Harada

IPC分类号： G03F7/027 ,  G03F7/20

CPC分类号： G03F7/0382 ,  G03F7/0046 ,  G03F7/0392 ,  G03F7/0395 ,  G03F7/0397 ,  G03F7/2041 ,  Y10S430/108 ,  Y10S430/111 ,  Y10S430/143

摘要： A resist composition comprises a base polymer which changes its alkali solubility under the action of an acid, and an additive copolymer comprising recurring units (a) and (b). R1 is F or CF3, R2 and R3 are H or alkyl or form a ring, R4 is H or an acid labile group, R5 to R6 are H, F, or alkyl, or two of R5 to R8 may together form a ring, m=0 or 1, 0.2≦a≦0.8, and 0.1≦b 0.6. A resist film of the composition has good barrier property against water so that leaching of the resist film with water is controlled, minimizing a change of pattern profile due to leach-out.

摘要翻译： 抗蚀剂组合物包含在酸的作用下改变其碱溶解性的基础聚合物和包含重复单元（a）和（b）的添加剂共聚物。 R1是F或CF3，R2和R3是H或烷基或形成环，R4是H或酸不稳定基团，R5至R6是H，F或烷基，或R5至R8中的两个可以一起形成环， m = 0或1，0.2 <= a <= 0.8，0.1 <= b 0.6。 该组合物的抗蚀剂膜对水具有良好的阻隔性，从而控制抗蚀剂膜与水的浸出，从而最小化由于浸出而导致的图案轮廓的变化。

公开(公告)号：US07622242B2

公开(公告)日：2009-11-24

申请号：US12236359

申请日：2008-09-23

申请人： Jun Hatakeyama ,  Koji Hasegawa ,  Takeru Watanabe ,  Yuji Harada

发明人： Jun Hatakeyama ,  Koji Hasegawa ,  Takeru Watanabe ,  Yuji Harada

IPC分类号： G03F7/039 ,  G03F7/038 ,  G03F7/20 ,  G03F7/30 ,  G03F7/38

CPC分类号： G03F7/0382 ,  G03F7/0046 ,  G03F7/0392 ,  G03F7/0395 ,  G03F7/0397 ,  G03F7/2041 ,  Y10S430/108 ,  Y10S430/111 ,  Y10S430/143

摘要： A resist composition comprises a base polymer which changes its alkali solubility under the action of an acid, and an additive copolymer comprising recurring units (a) and (b). R1 is F or CF3, R2 and R3 are H or alkyl or form a ring, R4 is H or an acid labile group, R5 to R6 are H, F, or alkyl, or two of R5 to R8 may together form a ring, m=0 or 1, 0.2≦a≦0.8, and 0.1≦b≦0.6. A resist film of the composition has good barrier property against water so that leaching of the resist film with water is controlled, minimizing a change of pattern profile due to leach-out.

摘要翻译： 抗蚀剂组合物包含在酸的作用下改变其碱溶解性的基础聚合物和包含重复单元（a）和（b）的添加剂共聚物。 R1是F或CF3，R2和R3是H或烷基或形成环，R4是H或酸不稳定基团，R5至R6是H，F或烷基，或R5至R8中的两个可以一起形成环， m = 0或1，0.2 <= a <= 0.8，0.1 <= b <= 0.6。 该组合物的抗蚀剂膜对水具有良好的阻隔性，从而控制抗蚀剂膜与水的浸出，从而最小化由于浸出而导致的图案轮廓的变化。

公开(公告)号：US06531627B2

公开(公告)日：2003-03-11

申请号：US09842007

申请日：2001-04-26

申请人： Tsunehiro Nishi ,  Koji Hasegawa ,  Takeru Watanabe ,  Takeshi Kinsho ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Jun Hatakeyama

发明人： Tsunehiro Nishi ,  Koji Hasegawa ,  Takeru Watanabe ,  Takeshi Kinsho ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Jun Hatakeyama

IPC分类号： C07C6974

CPC分类号： G03F7/039 ,  C07C69/716 ,  C08G61/08 ,  G03F7/0045

摘要： An ester compound of the following formula (1) is provided. R1 is H, methyl or CH2CO2R3, R2 is H, methyl or CO2R3, R3 is C1-C15 alkyl, R4 is branched or cyclic, tertiary C5-C20 alkyl group, Z is a divalent C1-C10 hydrocarbon group, and k is 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, and etching resistance, and is suited for micropatterning using electron beams or deep-UV.

摘要翻译： 提供下式（1）的酯化合物：R 1是H，甲基或CH 2 CO 2 R 3，R 2是H，甲基或CO 2 R 3，R 3是C 1 -C 15烷基，R 4是支链或环状的，叔C5-C20烷基，Z 是二价C1-C10烃基，k为0或1.含有由酯化合物得到的聚合物作为基础树脂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，以及 适用于使用电子束或深紫外线的微图案。

公开(公告)号：US06524765B1

公开(公告)日：2003-02-25

申请号：US09711311

申请日：2000-11-14

申请人： Tsunehiro Nishi ,  Takeru Watanabe ,  Jun Hatakeyama ,  Takeshi Kinsho ,  Koji Hasegawa ,  Seiichiro Tachibana

发明人： Tsunehiro Nishi ,  Takeru Watanabe ,  Jun Hatakeyama ,  Takeshi Kinsho ,  Koji Hasegawa ,  Seiichiro Tachibana

IPC分类号： G03F720

CPC分类号： G03F7/0045 ,  G03F7/0395 ,  Y10S430/106 ,  Y10S430/111

摘要： A polymer comprising units of formula (1-1) or (1-2) and having a weight average molecular weight of 1,000 to 500,000 is provided. R1 is an acid labile group, R2 is H or straight or branched C1-4 alkyl, Z is a tetravalent C2-10 hydrocarbon group, and k=0 or 1. A resist composition comprising the polymer as a base resin has significantly improved sensitivity, resolution and etching resistance and is very useful in microfabrication.

摘要翻译： 提供了包含式（1-1）或（1-2）单元并且具有1,000至500,000重均分子量的聚合物.R1是酸不稳定基团，R 2是H或直链或支链C 1-4烷基， Z是四价C2-10烃基，k = 0或1.包含聚合物作为基础树脂的抗蚀剂组合物具有显着提高的灵敏度，分辨率和耐蚀刻性，并且在微细加工中非常有用。

公开(公告)号：US06444396B1

公开(公告)日：2002-09-03

申请号：US09630810

申请日：2000-08-02

申请人： Takeru Watanabe ,  Takeshi Kinsho ,  Tsunehiro Nishi ,  Mutsuo Nakashima ,  Koji Hasegawa ,  Jun Hatakeyama

发明人： Takeru Watanabe ,  Takeshi Kinsho ,  Tsunehiro Nishi ,  Mutsuo Nakashima ,  Koji Hasegawa ,  Jun Hatakeyama

IPC分类号： G03F7039

CPC分类号： G03F7/039 ,  C07C69/753 ,  C07C2601/08 ,  C07C2601/10 ,  C07C2601/14 ,  C07C2601/16 ,  C07C2602/42 ,  C07C2603/86 ,  C08F32/08 ,  G03F7/0045 ,  Y02P20/55 ,  Y10S430/106

摘要： A novel ester compound having an alkylcycloalkyl or alkylcycloalkenyl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.

摘要翻译： 提供了具有烷基环烷基或烷基环烯基作为保护基的新型酯化合物以及包含酯化合物单元的聚合物。 聚合物用作基础树脂以配制具有比常规抗蚀剂组合物更高的灵敏度，分辨率和耐蚀刻性的抗蚀剂组合物。

公开(公告)号：US06962767B2

公开(公告)日：2005-11-08

申请号：US10315069

申请日：2002-12-10

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： G03F7/039 ,  C07D317/12 ,  C07D317/20 ,  C07D317/24 ,  C07D319/06 ,  C08F32/00 ,  C08F220/10 ,  C08F222/06 ,  C08F222/10 ,  C08G61/02 ,  C08G61/08 ,  G03C5/00

CPC分类号： C08G61/08 ,  C08G61/02 ,  Y10S430/106 ,  Y10S430/111

摘要： Acetal compounds in which a 5- or 6-membered ring acetal structure is connected to a norbornene structure through a linker represented by —(CH2)m— in which one hydrogen atom may be substituted with a hydroxyl or acetoxy group, and m is from 1 to 8 are novel. Using the acetal compounds as a monomer, polymers are obtained. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation and has excellent sensitivity, resolution, and etching resistance.

摘要翻译： 其中5或6元环缩醛结构通过 - （CH 2 CH 2）m - 表示的连接体与降冰片烯结构连接的缩醛化合物，其中一个氢 原子可以被羟基或乙酰氧基取代，m为1至8的是新的。 使用缩醛化合物作为单体，得到聚合物。 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，并且具有优异的灵敏度，分辨率和耐蚀刻性。

公开(公告)号：US06780563B2

公开(公告)日：2004-08-24

申请号：US09963465

申请日：2001-09-27

申请人： Koji Hasegawa ,  Takeshi Kinsho ,  Takeru Watanabe ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Tsunehiro Nishi ,  Jun Hatakeyama

发明人： Koji Hasegawa ,  Takeshi Kinsho ,  Takeru Watanabe ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Tsunehiro Nishi ,  Jun Hatakeyama

IPC分类号： G03F7039

CPC分类号： G03F7/0758 ,  G03F7/0045

摘要： A polymer bearing specific silicon-containing groups is novel. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation and has excellent sensitivity and resolution at a wavelength of less than 300 nm, and high resistance to oxygen plasma etching. The resist composition lends itself to micropatterning for the fabrication of VLSIs.

摘要翻译： 具有特定含硅基团的聚合物是新颖的。 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，并且在小于300nm的波长下具有优异的灵敏度和分辨率，以及高耐氧等离子体蚀刻性。 抗蚀剂组合物本身可用于制造VLSI的微图案。

公开(公告)号：US06670498B2

公开(公告)日：2003-12-30

申请号：US10288514

申请日：2002-11-06

申请人： Tsunehiro Nishi ,  Koji Hasegawa ,  Takeru Watanabe ,  Takeshi Kinsho ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Jun Hatakeyama

发明人： Tsunehiro Nishi ,  Koji Hasegawa ,  Takeru Watanabe ,  Takeshi Kinsho ,  Mutsuo Nakashima ,  Seiichiro Tachibana ,  Jun Hatakeyama

IPC分类号： C07C6974

CPC分类号： G03F7/039 ,  C07C69/716 ,  C08G61/08 ,  G03F7/0045

摘要： An ester compound of the following formula (1) is provided. R1 is H, methyl or CH2CO2R3, R2 is H, methyl or CO2R3, R3 is C1-C15 alkyl, R4 is branched or cyclic, tertiary C5-C20 alkyl group, Z is a divalent C1-C10 hydrocarbon group, and k is 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, and etching resistance, and is suited for micropatterning using electron beams or deep-UV.

摘要翻译： 提供下式（1）的酯化合物：R 1是H，甲基或CH 2 CO 2 R 3，R 2是H，甲基或CO 2 R 3，R 3是C 1 -C 15烷基 R 4是支链或环状的，叔C5-C20烷基，Z是二价C1-C10烃基，k是0或1.含有由酯化合物得到的聚合物作为基础树脂的抗蚀剂组合物是 对高能辐射敏感，具有优异的灵敏度，分辨率和耐蚀刻性，适用于使用电子束或深UV的微图案。

公开(公告)号：US06660448B2

公开(公告)日：2003-12-09

申请号：US09986274

申请日：2001-11-08

申请人： Seiichiro Tachibana ,  Mutsuo Nakashima ,  Tsunehiro Nishi ,  Takeshi Kinsho ,  Koji Hasegawa ,  Takeru Watanabe ,  Jun Hatakeyama

发明人： Seiichiro Tachibana ,  Mutsuo Nakashima ,  Tsunehiro Nishi ,  Takeshi Kinsho ,  Koji Hasegawa ,  Takeru Watanabe ,  Jun Hatakeyama

IPC分类号： C08F2400

CPC分类号： C08F222/06 ,  C08F232/08 ,  G03F7/0395 ,  G03F7/0397 ,  Y10S430/106 ,  Y10S430/111

摘要： The invention provides a polymer comprising recurring units containing bridged aliphatic rings in the backbone and having a hydroxyl, acyloxy or alkoxylcarbonyloxy group as well as a lactone structure bonded through a spacer, the polymer having a weight average molecular weight of 1,000-500,000. 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.