公开(公告)号：US07687222B2

公开(公告)日：2010-03-30

申请号：US11822444

申请日：2007-07-05

申请人： Takeru Watanabe ,  Takeshi Kinsho ,  Koji Hasegawa ,  Seiichiro Tachibana ,  Masaki Ohashi

发明人： Takeru Watanabe ,  Takeshi Kinsho ,  Koji Hasegawa ,  Seiichiro Tachibana ,  Masaki Ohashi

IPC分类号： G03F7/039 ,  G03F7/20 ,  G03F7/30 ,  G03F7/38 ,  C08F20/10

CPC分类号： G03F7/0397 ,  C07C67/11 ,  C07C69/54 ,  C07C2601/14 ,  C07C2602/42 ,  C07C2602/46 ,  C07C2603/68 ,  C07C2603/74 ,  C08F220/28 ,  C08F222/06 ,  G03F7/0046 ,  G03F7/0395

摘要： Novel polymerizable ester compounds having formulae (1) to (4) undergo no acid-induced decomposition by β-elimination wherein A1 is a polymerizable functional group having a carbon-carbon double bond, R1 is H or —C—(R5)3, R2 and R3 are alkyl, R4 is H or alkyl, R5 is a monovalent hydrocarbon group, X is alkylene, Y is methylene, ethylene or isopropylidene, Z is alkylene, and n=1 or 2. Resist compositions comprising polymers derived from the ester compounds have excellent sensitivity and resolution and lend themselves to micropatterning lithography.

摘要翻译： 具有式（1）〜（4）的新型聚合性酯化合物，其中A1是具有碳 - 碳双键的可聚合官能团，R1是H或-C-（R5）3），不会发生酸分解 ，R2和R3是烷基，R4是H或烷基，R5是一价烃基，X是亚烷基，Y是亚甲基，亚乙基或异亚丙基，Z是亚烷基，n = 1或2.抗蚀剂组合物包含衍生自 酯化合物具有优异的灵敏度和分辨率，并适用于微图案光刻。

公开(公告)号：US20090239179A1

公开(公告)日：2009-09-24

申请号：US12405670

申请日：2009-03-17

申请人： Takeshi Kinsho ,  Masaki Ohashi ,  Koji Hasegawa ,  Takeru Watanabe

发明人： Takeshi Kinsho ,  Masaki Ohashi ,  Koji Hasegawa ,  Takeru Watanabe

IPC分类号： G03F7/20 ,  C07C69/54 ,  C08F20/10

CPC分类号： G03F7/0392 ,  C07C69/54 ,  C07C2601/08 ,  C07C2602/42 ,  C07C2603/74 ,  C08F220/18 ,  G03F7/0397 ,  Y10S430/108 ,  Y10S430/111

摘要： A hydroxyl-containing monomer of formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are monovalent C1-C15 hydrocarbon groups, or R2 and R3 may form an aliphatic ring. The monomers are useful for the synthesis of polymers which have high transparency to radiation of up to 500 nm and the effect of controlling acid diffusion so that the polymers may be used as a base resin to formulate radiation-sensitive resist compositions having a high resolution.

摘要翻译： 提供式（1）的含羟基的单体，其中R 1是H，F，甲基或三氟甲基，R 2和R 3是一价C 1 -C 15烃基，或者R 2和R 3可以形成脂族环。 单体可用于合成对高达500nm的辐射具有高透明度的聚合物，以及控制酸扩散的效果，使得聚合物可用作基础树脂以配制具有高分辨率的辐射敏感性抗蚀剂组合物。

公开(公告)号：US20060093960A1

公开(公告)日：2006-05-04

申请号：US11258894

申请日：2005-10-27

申请人： Takeshi Kinsho ,  Takeru Watanabe ,  Masaki Ohashi ,  Koji Hasegawa ,  Seiichiro Tachibana

发明人： Takeshi Kinsho ,  Takeru Watanabe ,  Masaki Ohashi ,  Koji Hasegawa ,  Seiichiro Tachibana

IPC分类号： G03C1/76

CPC分类号： G03F7/0395 ,  C07D307/20 ,  C07D309/10 ,  C07D319/06 ,  C07D319/08 ,  C08F220/18 ,  C08F220/24 ,  G03F7/0046 ,  G03F7/0397

摘要： Cyclic structure-bearing fluorinated monomers having formula (1) wherein Z is a divalent organic group containing a polymerizable unsaturated group are useful to produce polymers for the manufacture of radiation-sensitive resist compositions which are fully transparent to radiation having a wavelength of up to 300 nm and have improved development properties.

公开(公告)号：US07998657B2

公开(公告)日：2011-08-16

申请号：US12912161

申请日：2010-10-26

申请人： Masaki Ohashi ,  Takeshi Kinsho ,  Takeru Watanabe

发明人： Masaki Ohashi ,  Takeshi Kinsho ,  Takeru Watanabe

IPC分类号： G03F7/004 ,  G03F7/30 ,  C08F124/00 ,  C08F224/00

CPC分类号： G03F7/0395 ,  C07D307/20 ,  C07D307/77 ,  C07D309/10 ,  C08F20/26 ,  C08F20/28 ,  C08F222/06 ,  C08F232/04 ,  G03F7/0046 ,  G03F7/0397 ,  Y10S430/111

摘要： Novel ester compounds having formulae (1) to (4) wherein A1 is a polymerizable functional group having a carbon-carbon double bond, A2 is oxygen, methylene or ethylene, R1 is a monovalent hydrocarbon group, R2 is H or a monovalent hydrocarbon group, any pair of R1 and/or R2 may form an aliphatic hydrocarbon ring, R3 is a monovalent hydrocarbon group, and n is 0 to 6 are polymerizable into polymers. Resist compositions comprising the polymers as a base resin are thermally stable and sensitive to high-energy radiation, have excellent sensitivity and resolution, and lend themselves to micropatterning with electron beam or deep-UV.

公开(公告)号：US07902385B2

公开(公告)日：2011-03-08

申请号：US11822441

申请日：2007-07-05

申请人： Masaki Ohashi ,  Takeshi Kinsho ,  Takeru Watanabe

发明人： Masaki Ohashi ,  Takeshi Kinsho ,  Takeru Watanabe

IPC分类号： C07D307/02

CPC分类号： G03F7/0395 ,  C07D307/20 ,  C07D307/77 ,  C07D309/10 ,  C08F20/26 ,  C08F20/28 ,  C08F222/06 ,  C08F232/04 ,  G03F7/0046 ,  G03F7/0397 ,  Y10S430/111

摘要： Novel ester compounds having formulae (1) to (4) wherein A1 is a polymerizable functional group having a carbon-carbon double bond, A2 is oxygen, methylene or ethylene, R1 is a monovalent hydrocarbon group, R2 is H or a monovalent hydrocarbon group, any pair of R1 and/or R2 may form an aliphatic hydrocarbon ring, R3 is a monovalent hydrocarbon group, and n is 0 to 6 are polymerizable into polymers. Resist compositions comprising the polymers as a base resin are thermally stable and sensitive to high-energy radiation, have excellent sensitivity and resolution, and lend themselves to micropatterning with electron beam or deep-UV.

摘要翻译： 具有式（1）至（4）的新型酯化合物，其中A1是具有碳 - 碳双键的可聚合官能团，A2是氧，亚甲基或亚乙基，R1是一价烃基，R2是H或一价烃基 任何一个R 1和/或R 2可以形成脂族烃环，R 3是一价烃基，n是0-6，可聚合成聚合物。 包含作为基础树脂的聚合物的抗蚀剂组合物是热稳定的并且对高能量辐射敏感，具有优异的灵敏度和分辨率，并且借助于电子束或深紫外线来进行微图案化。

公开(公告)号：US20110039204A1

公开(公告)日：2011-02-17

申请号：US12912161

申请日：2010-10-26

申请人： Masaki OHASHI ,  Takeshi Kinsho ,  Takeru Watanabe

发明人： Masaki OHASHI ,  Takeshi Kinsho ,  Takeru Watanabe

IPC分类号： G03F7/004 ,  C08G63/66 ,  G03F7/20

CPC分类号： G03F7/0395 ,  C07D307/20 ,  C07D307/77 ,  C07D309/10 ,  C08F20/26 ,  C08F20/28 ,  C08F222/06 ,  C08F232/04 ,  G03F7/0046 ,  G03F7/0397 ,  Y10S430/111

摘要： Novel ester compounds having formulae (1) to (4) wherein A1 is a polymerizable functional group having a carbon-carbon double bond, A2 is oxygen, methylene or ethylene, R1 is a monovalent hydrocarbon group, R2 is H or a monovalent hydrocarbon group, any pair of R1 and/or R2 may form an aliphatic hydrocarbon ring, R3 is a monovalent hydrocarbon group, and n is 0 to 6 are polymerizable into polymers. Resist compositions comprising the polymers as a base resin are thermally stable and sensitive to high-energy radiation, have excellent sensitivity and resolution, and lend themselves to micropatterning with electron beam or deep-UV.

摘要翻译： 具有式（1）至（4）的新型酯化合物，其中A1是具有碳 - 碳双键的可聚合官能团，A2是氧，亚甲基或亚乙基，R1是一价烃基，R2是H或一价烃基 任何一个R 1和/或R 2可以形成脂族烃环，R 3是一价烃基，n是0-6，可聚合成聚合物。 包含作为基础树脂的聚合物的抗蚀剂组合物是热稳定的并且对高能量辐射敏感，具有优异的灵敏度和分辨率，并且借助于电子束或深紫外线来进行微图案化。

公开(公告)号：US07531289B2

公开(公告)日：2009-05-12

申请号：US11258894

申请日：2005-10-27

申请人： Takeshi Kinsho ,  Takeru Watanabe ,  Masaki Ohashi ,  Koji Hasegawa ,  Seiichiro Tachibana

发明人： Takeshi Kinsho ,  Takeru Watanabe ,  Masaki Ohashi ,  Koji Hasegawa ,  Seiichiro Tachibana

IPC分类号： G03F7/039 ,  C08F18/20 ,  C07D315/00

CPC分类号： G03F7/0395 ,  C07D307/20 ,  C07D309/10 ,  C07D319/06 ,  C07D319/08 ,  C08F220/18 ,  C08F220/24 ,  G03F7/0046 ,  G03F7/0397

摘要： Cyclic structure-bearing fluorinated monomers having formula (1) wherein Z is a divalent organic group containing a polymerizable unsaturated group are useful to produce polymers for the manufacture of radiation-sensitive resist compositions which are fully transparent to radiation having a wavelength of up to 300 nm and have improved development properties.

摘要翻译： 具有式（1）的带有结构式的氟化单体，其中Z是含有可聚合不饱和基团的二价有机基团，可用于制备用于制造辐射敏感性抗蚀剂组合物的聚合物，其对波长高达300nm的辐射是完全透明的 nm，具有改善的显影性能。

公开(公告)号：US20070179309A1

公开(公告)日：2007-08-02

申请号：US11699390

申请日：2007-01-30

申请人： Koji Hasegawa ,  Takeshi Kinsho ,  Tsunehiro Nishi ,  Masaki Ohashi ,  Takeru Watanabe

发明人： Koji Hasegawa ,  Takeshi Kinsho ,  Tsunehiro Nishi ,  Masaki Ohashi ,  Takeru Watanabe

IPC分类号： C07C69/63 ,  C07C31/34

CPC分类号： G03F7/0395 ,  C07C29/147 ,  C07C69/54 ,  C07C69/653 ,  C07C69/753 ,  C07C2601/08 ,  C07C2601/14 ,  C07C2602/42 ,  C08F220/24 ,  C08F220/28 ,  C08F232/08 ,  G03F7/0046 ,  G03F7/0397 ,  C07C31/44 ,  C07C31/42 ,  C07C35/48

摘要： Fluoroalcohol compounds of formula (4) are prepared by reacting a fluorine compound of formula (1) with reducing agents or organometallic reagents of formulas (2) and (3) wherein R1 is H or a monovalent C1-C20 hydrocarbon group in which any —CH2— moiety may be replaced by —O— or —C(═O)—, R2 is H or a monovalent C1-C6 hydrocarbon group, R3 and R4 are H or a monovalent C1-C8 hydrocarbon group, and M1 is Li, Na, K, Mg, Zn, Al, B, or Si. From the fluoroalcohol compounds, fluorinated monomers can be produced in a simple and economic way, which are useful in producing polymers for the formulation of radiation-sensitive resist compositions.

摘要翻译： 通式（1）的氟化合物与式（2）和（3）的还原剂或式（2）和（3）的有机金属试剂反应制备式（4）的氟化醇，其中R 1是H或单价C 其中任何-CH 2 - 部分可被-O-或-C（ - ） - 取代的 - ， - R 2是H或一价C 1 -C 6烃基，R 3和R 4 > 4是H或一价C 1 -C 8烃基，M 1是Li，Na，K， Mg，Zn，Al，B或Si。 从氟代醇化合物可以以简单且经济的方式制备氟化单体，其可用于制备用于制备辐射敏感抗蚀剂组合物的聚合物。

公开(公告)号：US08808964B2

公开(公告)日：2014-08-19

申请号：US13217319

申请日：2011-08-25

申请人： Masayoshi Sagehashi ,  Takeru Watanabe ,  Tomohiro Kobayashi

发明人： Masayoshi Sagehashi ,  Takeru Watanabe ,  Tomohiro Kobayashi

IPC分类号： G03F7/004

CPC分类号： C07D235/08 ,  C07D233/60 ,  G03F7/0045 ,  G03F7/0397

摘要： An aralkylcarbamate of imidazole base is effective as the quencher. In a chemically amplified positive resist composition comprising the carbamate, deprotection reaction of carbamate takes place by reacting with the acid generated upon exposure to high-energy radiation, whereby the composition changes its basicity before and after exposure, resulting in a pattern profile with advantages including high resolution, rectangular shape, and minimized dark-bright difference.

摘要翻译： 咪唑碱的芳烷基氨基甲酸酯作为猝灭剂是有效的。 在包含氨基甲酸酯的化学放大型正性抗蚀剂组合物中，氨基甲酸酯的脱保护反应通过与暴露于高能量辐射时产生的酸反应而发生，由此组合物在暴露之前和之后改变其碱度，得到具有以下优点的图案图案，包括 高分辨率，矩形形状和最小暗亮差异。

公开(公告)号：US08778591B2

公开(公告)日：2014-07-15

申请号：US13217319

申请日：2011-08-25

申请人： Masayoshi Sagehashi ,  Takeru Watanabe ,  Tomohiro Kobayashi

发明人： Masayoshi Sagehashi ,  Takeru Watanabe ,  Tomohiro Kobayashi

IPC分类号： G03F7/004

摘要： An aralkylcarbamate of imidazole base is effective as the quencher. In a chemically amplified positive resist composition comprising the carbamate, deprotection reaction of carbamate takes place by reacting with the acid generated upon exposure to high-energy radiation, whereby the composition changes its basicity before and after exposure, resulting in a pattern profile with advantages including high resolution, rectangular shape, and minimized dark-bright difference.