公开(公告)号：US07135269B2

公开(公告)日：2006-11-14

申请号：US10765919

申请日：2004-01-29

申请人： Jun Hatakeyama ,  Takanobu Takeda ,  Osamu Watanabe

发明人： Jun Hatakeyama ,  Takanobu Takeda ,  Osamu Watanabe

IPC分类号： G03C1/73 ,  G03F7/039 ,  G03F7/30 ,  G03F7/36 ,  C08F30/08 ,  C08F24/00

CPC分类号： G03F7/0395 ,  C08F220/28 ,  C08F222/20 ,  C08F230/08 ,  C08F232/08 ,  G03F7/0397 ,  G03F7/0758

摘要： A polymer comprising recurring units containing silicon and recurring units having a substituent group of formula (1) is novel wherein A1 is a divalent group selected from furandiyl, tetrahydrofurandiyl and oxanorbornanediyl, R1 and R2 are selected from monovalent C1–C10 hydrocarbon groups, or R1 and R2 taken together may form an aliphatic hydrocarbon ring with the carbon atom, and R3 is hydrogen or a monovalent C1–C10 hydrocarbon group which may contain a hetero atom. The polymer is useful as a base resin to formulate a resist composition which is sensitive to high-energy radiation, and has excellent sensitivity and resolution at a wavelength of less than 300 nm as well as satisfactory oxygen plasma etching resistance.

摘要翻译： 含有硅的重复单元和具有式（1）的取代基的重复单元的聚合物是新颖的，其中A 1是选自呋喃二基，四氢呋喃基和氧杂甘露二烷基的二价基团，R 1， SUP>和R 2选自单价C 1 -C 10烃基或R 1和R 2 一起可以与碳原子一起形成脂族烃环，R 3是氢或一价C 1 -C 1 - 10个可以含有杂原子的烃基。 聚合物可用作基础树脂以配制对高能辐射敏感的抗蚀剂组合物，并且在小于300nm的波长下具有优异的灵敏度和分辨率以及满意的氧等离子体耐蚀刻性。

公开(公告)号：US06692893B2

公开(公告)日：2004-02-17

申请号：US09983155

申请日：2001-10-23

申请人： Youichi Ohsawa ,  Jun Watanabe ,  Takeshi Nagata ,  Jun Hatakeyama

发明人： Youichi Ohsawa ,  Jun Watanabe ,  Takeshi Nagata ,  Jun Hatakeyama

IPC分类号： G03C173

CPC分类号： G03F7/0045 ,  G03F7/0382 ,  G03F7/0392 ,  G03F7/0397 ,  Y10S430/115 ,  Y10S430/12 ,  Y10S430/122 ,  Y10S430/126

摘要： Onium salts of arylsulfonyloxynaphthalenesulfonate anions with iodonium or sulfonium cations are novel. A chemically amplified resist composition comprising the onium salt as a photoacid generator is suited for microfabrication, especially by deep UV lithography because of many advantages including improved resolution, improved focal latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris after coating, development and peeling, and improved pattern profile after development.

摘要翻译： 芳基磺酰氧基萘磺酸盐与碘鎓或锍阳离子的鎓盐是新颖的。 包含作为光致酸发生剂的鎓盐的化学放大抗蚀剂组合物特别适用于微细加工，特别是通过深紫外光刻技术，因为许多优点，包括改进的分辨率，改善的焦点纬度，最小化的线宽变化或甚至在长期PED下的形状退化 涂层，显影和剥离后的碎屑，以及显影后改进的图案轮廓。

公开(公告)号：US06746817B2

公开(公告)日：2004-06-08

申请号：US09984726

申请日：2001-10-31

申请人： Takanobu Takeda ,  Jun Hatakeyama ,  Osamu Watanabe ,  Hiroshi Kubota

发明人： Takanobu Takeda ,  Jun Hatakeyama ,  Osamu Watanabe ,  Hiroshi Kubota

IPC分类号： G03C173

CPC分类号： C08K5/13 ,  C08F232/08 ,  C08K5/36 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/106 ,  Y10S430/108 ,  Y10S430/111 ,  Y10S430/115

摘要： A polymer comprises recurring units of formula (1) and recurring units having acid labile groups which units increase alkali solubility as a result of the acid labile groups being decomposed under the action of acid, and has a Mw of 1,000-500,000. R1 and R2 each are hydrogen, hydroxyl, hydroxyalkyl, alkyl, alkoxy or halogen, and n is 0, 1, 2, 3 or 4. The polymer is useful as a base resin to form a chemically amplified, positive resist composition which has advantages including a significantly enhanced contrast of alkali dissolution rate before and after exposure, high sensitivity, high resolution, and high etching resistance and is best suited as a micropatterning material for use in VLSI manufacture.

摘要翻译： 聚合物包含式（1）的重复单元和具有酸不稳定基团的重复单元，该单元由于酸不稳定基团在酸的作用下分解而增加碱溶解度，并且具有1,000-500,000的Mw .R <1 >和R 2各自为氢，羟基，羟基烷基，烷基，烷氧基或卤素，n为0,1,2,3或4.该聚合物可用作基础树脂以形成化学增强正性抗蚀剂组合物 其具有显着增强曝光前后碱溶解速度对比度，高灵敏度，高分辨率和高耐腐蚀性的优点，并且最适用于用于VLSI制造的微图案材料。

公开(公告)号：US20050260521A1

公开(公告)日：2005-11-24

申请号：US10765919

申请日：2004-01-29

申请人： Jun Hatakeyama ,  Takanobu Takeda ,  Osamu Watanabe

发明人： Jun Hatakeyama ,  Takanobu Takeda ,  Osamu Watanabe

IPC分类号： G03C1/492 ,  G03F7/039 ,  G03F7/075

CPC分类号： G03F7/0395 ,  C08F220/28 ,  C08F222/20 ,  C08F230/08 ,  C08F232/08 ,  G03F7/0397 ,  G03F7/0758

摘要： A polymer comprising recurring units containing silicon and recurring units having a substituent group of formula (1) is novel wherein A1 is a divalent group selected from furandiyl, tetrahydrofurandiyl and oxanorbornanediyl, R1 and R2 are selected from monovalent C1-C10 hydrocarbon groups, or R1 and R2 taken together may form an aliphatic hydrocarbon ring with the carbon atom, and R3 is hydrogen or a monovalent C1-C10 hydrocarbon group which may contain a hetero atom. The polymer is useful as a base resin to formulate a resist composition which is sensitive to high-energy radiation, and has excellent sensitivity and resolution at a wavelength of less than 300 nm as well as satisfactory oxygen plasma etching resistance.

摘要翻译： 含有硅的重复单元和具有式（1）的取代基的重复单元的聚合物是新颖的，其中A 1是选自呋喃二基，四氢呋喃基和氧杂甘露二烷基的二价基团，R 1， SO 2和R 2选自单价C 1 -C 10烃基或R 1和R 2 一起可以与碳原子一起形成脂族烃环，R 3是氢或一价C 1 -C 1 - 10个可以含有杂原子的烃基。 聚合物可用作基础树脂以配制对高能辐射敏感的抗蚀剂组合物，并且在小于300nm的波长下具有优异的灵敏度和分辨率以及满意的氧等离子体耐蚀刻性。

公开(公告)号：US06312867B1

公开(公告)日：2001-11-06

申请号：US09431139

申请日：1999-11-01

申请人： Takeshi Kinsho ,  Tsunehiro Nishi ,  Hideshi Kurihara ,  Koji Hasegawa ,  Takeru Watanabe ,  Osamu Watanabe ,  Mutsuo Nakashima ,  Takanobu Takeda ,  Jun Hatakeyama

发明人： Takeshi Kinsho ,  Tsunehiro Nishi ,  Hideshi Kurihara ,  Koji Hasegawa ,  Takeru Watanabe ,  Osamu Watanabe ,  Mutsuo Nakashima ,  Takanobu Takeda ,  Jun Hatakeyama

IPC分类号： G03F7004

CPC分类号： C07C69/56 ,  C07C69/013 ,  C07C69/533 ,  C07C69/54 ,  C07C69/593 ,  C07C69/60 ,  C07C2602/42 ,  C07C2603/68 ,  C07C2603/86 ,  C08F20/18 ,  G03F7/0045 ,  G03F7/039 ,  Y02P20/55

摘要： A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl 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.

公开(公告)号：US06730453B2

公开(公告)日：2004-05-04

申请号：US09887320

申请日：2001-06-25

申请人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

发明人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

IPC分类号： G03F7075

CPC分类号： G03F7/0045 ,  C08G77/14 ,  C08G77/38 ,  C08G77/388 ,  C08G77/50 ,  G03F7/0392 ,  G03F7/0757

摘要： The invention provides a high molecular weight silicone compound comprising recurring units of formula (1) and having a weight average molecular weight of 1,000-50,000. Some or all of the hydrogen atoms of carboxyl groups or carboxyl and hydroxyl groups in the silicone compound may be replaced by acid labile groups. Z is a di- to hexavalent, non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; Z is a di- to hexavalent, normal or branched hydrocarbon group or non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; x, y and z are integers of 1-5 corresponding to the valence of Z and Z′; R1 is —OCHR—R′—OH or —NHCHR—R′—OH; R2 is alkyl or alkenyl or a monovalent, non-aromatic, polycyclic hydrocarbon or bridged cyclic hydrocarbon group; p1, p2, p3 and p4 are 0 or positive numbers. A resist composition comprising the high molecular weight silicone compound as a base resin is sensitive to actinic radiation and has a high sensitivity and resolution so that it is suitable for microfabrication with electron beams or deep UV. Since the composition has low absorption at the exposure wavelength of an ArF or KrF excimer laser, a finely defined pattern having walls perpendicular to the substrate can be readily formed.

摘要翻译： 本发明提供了包含式（1）的重复单元并且具有1,000-50,000重均分子量的高分子量硅氧烷化合物。 硅氧烷化合物中的羧基或羧基和羟基的一些或全部氢原子可被酸不稳定基团取代.Z为二价至六价，非芳香族，单环或多环烃或桥环状烃基; Z是二价至六价，正或支链烃基或非芳香族单环或多环烃或桥环状烃基; x，y和z是对应于Z和Z'的化合价的1-5的整数; R 1是-OCHR-R'-OH或-NHCHR-R'-OH; R 2是烷基或烯基或单价，非芳族，多环烃或桥连环烃基; p1，p2，p3和p4为0或正数。 包含作为基础树脂的高分子量硅氧烷化合物的抗蚀剂组合物对光化辐射敏感，并且具有高灵敏度和分辨率，使得它适合于用电子束或深紫外线的微细加工。 由于组成在ArF或KrF准分子激光器的曝光波长处具有低吸收，因此可以容易地形成具有垂直于衬底的壁的精细限定图案。

公开(公告)号：US06309796B1

公开(公告)日：2001-10-30

申请号：US09129950

申请日：1998-08-06

申请人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

发明人： Mutsuo Nakashima ,  Ichiro Kaneko ,  Toshinobu Ishihara ,  Junji Tsuchiya ,  Jun Hatakeyama ,  Shigehiro Nagura

IPC分类号： G03F7075

CPC分类号： G03F7/0045 ,  C08G77/14 ,  C08G77/38 ,  C08G77/388 ,  C08G77/50 ,  G03F7/0392 ,  G03F7/0757

摘要： The invention provides a high molecular weight silicone compound comprising recurring units of formula (1) and having a weight average molecular weight of 1,000-50,000. Some or all of the hydrogen atoms of carboxyl groups or carboxyl and hydroxyl groups in the silicone compound may be replaced by acid labile groups. Z is di- to hexavalent, non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; Z′ is a di- to hexavalent, normal or branched hydrocarbon group or non-aromatic, monocyclic or polycyclic hydrocarbon or bridged cyclic hydrocarbon group; x, y and z are integers of 1-5 corresponding to the valence of Z and Z′; R1 is —OCHR—R′ —OH or —NHCHR—R′ —OH; R2 is alkyl or alkenyl or a monovalent, non-aromatic, polycyclic hydrocarbon or bridged cyclic hydrocarbon group; p1, p2, p3 and p4 are 0 or positive numbers. A resist composition comprising the high molecular weight silicone compound as a base resin is sensitive to actinic radiation and has a high sensitivity and resolution so that it is suitable for microfabrication with electron beams or deep UV. Since the composition has low absorption at the exposure wavelength of an ArF or KrF excimer laser, a finely defined pattern having walls perpendicular to the substrate can be readily formed.

摘要翻译： 本发明提供了包含式（1）的重复单元并且具有1,000-50,000重均分子量的高分子量硅氧烷化合物。 硅烷化合物中的羧基或羧基和羟基的一部分或全部氢原子可被酸不稳定基团取代.Z为二价至六价，非芳香族，单环或多环烃基或桥环状烃基; Z'是二价至六价，正或支链烃基或非芳香族单环或多环烃或桥连环烃基; x，y和z是对应于Z和Z'的化合价的1-5的整数; R 1是-OCHR-R'-OH或-NHCHR-R'-OH; R2是烷基或链烯基或单价，非芳族，多环烃或桥连环烃基; p1，p2，p3和p4为0或正数。 包含作为基础树脂的高分子量硅氧烷化合物的抗蚀剂组合物对光化辐射敏感，并且具有高灵敏度和分辨率，使得它适合于用电子束或深紫外线的微细加工。 由于组成在ArF或KrF准分子激光器的曝光波长处具有低吸收，因此可以容易地形成具有垂直于衬底的壁的精细限定图案。

公开(公告)号：US08507175B2

公开(公告)日：2013-08-13

申请号：US12905426

申请日：2010-10-15

申请人： Jun Hatakeyama ,  Masaki Ohashi ,  Youichi Ohsawa ,  Kazuhiro Katayama

发明人： Jun Hatakeyama ,  Masaki Ohashi ,  Youichi Ohsawa ,  Kazuhiro Katayama

IPC分类号： G03F7/00 ,  G03F7/004 ,  G03F7/20 ,  G03F7/028

CPC分类号： G03F7/0045 ,  G03F7/0397 ,  G03F7/095

摘要： The process forms a pattern by applying a resist composition onto a substrate to form a resist film, baking, exposure, post-exposure baking, and development. The resist composition comprises a polymer comprising recurring units having an acid labile group and substantially insoluble in alkaline developer, a PAG, a PBG capable of generating an amino group, a quencher for neutralizing the acid from PAG for inactivation, and an organic solvent. A total amount of amino groups from the quencher and PBG is greater than an amount of acid from PAG. An unexposed region and an over-exposed region are not dissolved in developer whereas only an intermediate exposure dose region is dissolved in developer. Resolution is doubled by splitting a single line into two through single exposure and development.

摘要翻译： 该方法通过将抗蚀剂组合物施加到基底上以形成抗蚀剂膜，烘烤，曝光，曝光后烘烤和显影来形成图案。 抗蚀剂组合物包含聚合物，其包含具有酸不稳定基团并且基本上不溶于碱性显影剂的重复单元，PAG，能够产生氨基的PBG，用于中和PAG酸失活的猝灭剂和有机溶剂。 来自猝灭剂和PBG的氨基的总量大于来自PAG的酸的量。 未曝光区域和过度曝光区域不溶解在显影剂中，而只有中间曝光剂量区域溶解在显影剂中。 通过单次曝光和开发将单线分成两组，分辨率翻了一番。

公开(公告)号：US08105748B2

公开(公告)日：2012-01-31

申请号：US12580953

申请日：2009-10-16

申请人： Masaki Ohashi ,  Youichi Ohsawa ,  Takeshi Kinsho ,  Jun Hatakeyama ,  Seiichiro Tachibana

发明人： Masaki Ohashi ,  Youichi Ohsawa ,  Takeshi Kinsho ,  Jun Hatakeyama ,  Seiichiro Tachibana

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

CPC分类号： C07D307/77 ,  C07C309/12 ,  C07C381/12 ,  C08F2220/303 ,  C08F2220/382 ,  G03F7/0045 ,  G03F7/0397 ,  G03F7/2041 ,  Y10S430/108 ,  Y10S430/111 ,  Y10S430/143

摘要： A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C2-C20 hydrocarbon group having cyclic structure, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.

摘要翻译： 提供了具有式（1）的可聚合阴离子的锍盐，其中R 1是H，F，甲基或三氟甲基，R 2，R 3和R 4是C 1 -C 10烷基，烯基或氧代烷基或C 6 -C 18芳基，芳烷基或芳氧基烷基，或 R 2，R 3和R 4中的两个可以键合在一起形成具有S的环，A是具有环状结构的C 2 -C 20烃基，n是0或1.锍盐在暴露于高温下时产生非常强的磺酸， 能量辐射。 还提供了包含衍生自锍盐的聚合物的抗蚀剂组合物。

公开(公告)号：US08048610B2

公开(公告)日：2011-11-01

申请号：US12428933

申请日：2009-04-23

申请人： Youichi Ohsawa ,  Jun Hatakeyama ,  Seiichiro Tachibana ,  Takeshi Kinsho

发明人： Youichi Ohsawa ,  Jun Hatakeyama ,  Seiichiro Tachibana ,  Takeshi Kinsho

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

CPC分类号： G03F7/0045 ,  C08F220/18 ,  C08F220/28 ,  C08F220/30 ,  C08F220/38 ,  G03F7/0392 ,  G03F7/0397 ,  G03F7/2041 ,  Y10S430/143 ,  Y10S430/167

摘要： A polymer comprising recurring units having formulae (1), (2) and (3) is provided as well as a chemically amplified resist composition comprising the same. R1 is H, F, CH3 or CF3, Rf is H, F, CF3 or C2F5, A is an optionally fluorine or oxygen-substituted divalent organic group, R2, R3 and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or may form a ring with the sulfur atom, N=0-2, R8 is H or alkyl, B is a single bond or optionally oxygen-substituted divalent organic group, a=0-3, b=1-3, and X is an acid labile group. The polymer generates a strong sulfonic acid which provides for effective cleavage of acid labile groups in a chemically amplified resist composition.

摘要翻译： 提供了包含具有式（1），（2）和（3）的重复单元的聚合物以及包含其的化学放大抗蚀剂组合物。 R 1是H，F，CH 3或CF 3，R f是H，F，CF 3或C 2 F 5，A是任选氟或氧取代的二价有机基团，R 2，R 3和R 4是烷基，烯基，氧代烷基，芳基，芳烷基或芳氧基烷基 或者可以与硫原子形成环，N = O-2，R 8是H或烷基，B是单键或任选的氧取代的二价有机基团，a = 0-3，b = 1-3，和 X是酸不稳定组。 该聚合物产生强的磺酸，其提供化学增强抗蚀剂组合物中酸不稳定基团的有效切割。