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1. 发明授权

US5929271A Compounds for use in a positive-working resist composition 失效
标题翻译：用于正性抗蚀剂组合物的化合物
公开(公告)号：US5929271A
公开(公告)日：1999-07-27
申请号：US912123
申请日：1997-08-15
申请人： Hideo Hada , Kazufumi Sato , Hiroshi Komano , Toshimasa Nakayama
发明人： Hideo Hada , Kazufumi Sato , Hiroshi Komano , Toshimasa Nakayama
IPC分类号： C07C69/013 , G03F7/004 , G03F7/039 , C07C69/74
CPC分类号： C07C69/013 , G03F7/0045 , G03F7/039 , Y10S430/115 , Y10S430/122
摘要： Proposed is novel compounds for use in a chemical-sensitization positive-working photoresist composition used in the photolithographic patterning process for the manufacture of fine electronic devices, which is capable of giving, with high photosensitivity to ArF excimer laser beams, a patterned resist layer having an excellently orthogonal cross sectional profile and high resistance against dry etching and exhibiting good adhesion to the substrate surface. While the composition comprises (A) a film-forming resinous ingredient which causes an increase of alkali solubility by interacting with an acid and (B) a radiation-sensitive acid-generating agent, the most characteristic feature of the invention consists in the use of a specific acrylic resin as the component (A), which comprises the monomeric units of a (meth)acrylic acid ester of hydroxy bicyclo�3.1.1!heptanone unsubstituted or substituted by an alkyl group such as hydroxypinanone (meth)acrylate, optionally, in combination with the monomeric units derived from (meth)acrylic acid and/or tert-butyl (meth)acrylate in a molar fraction of 3:7 to 7:3.
摘要翻译：提出了用于制造精细电子器件的光刻图案化方法中使用的化学增感正性光致抗蚀剂组合物中的新化合物，其能够赋予ArF准分子激光束具有高光敏性的图案化抗蚀剂层，其具有具有优异的正交横截面轮廓和高耐干腐蚀性，并且对基材表面表现出良好的粘合性。虽然组合物包含（A）通过与酸相互作用引起碱溶解度增加的成膜树脂成分和（B）辐射敏感的酸产生剂，但是本发明的最特征在于使用作为组分（A）的特定丙烯酸树脂，其包含未被取代或被烷基如羟基酮（甲基）丙烯酸酯取代的羟基双环[3.1.1]庚酮的（甲基）丙烯酸酯的单体单元，与来自（甲基）丙烯酸和/或（甲基）丙烯酸叔丁酯的单体单元组合，摩尔分数为3:7至7:3。

2. 发明授权

US6077644A Positive-working resist composition 失效
标题翻译：正面抗蚀剂组成
公开(公告)号：US6077644A
公开(公告)日：2000-06-20
申请号：US207202
申请日：1998-12-08
申请人： Hideo Hada , Kazufumi Sato , Hiroshi Komano , Toshimasa Nakayama
发明人： Hideo Hada , Kazufumi Sato , Hiroshi Komano , Toshimasa Nakayama
IPC分类号： C07C69/013 , G03F7/004 , G03F7/039
CPC分类号： C07C69/013 , G03F7/0045 , G03F7/039 , Y10S430/115 , Y10S430/122
摘要： Proposed is a novel chemical-sensitization positive-working photoresist composition used in the photolithographic patterning process for the manufacture of fine electronic devices, which is capable of giving, with high photosensitivity to ArF excimer laser beams, a patterned resist layer having an excellently orthogonal cross sectional profile and high resistance against dry etching and exhibiting good adhesion to the substrate surface. While the composition comprises (A) a film-forming resinous ingredient which undergoes an increase of alkali solubility by interacting with an acid and (B) a radiation-sensitive acid-generating agent, the most characteristic feature of the invention consists in the use of a specific acrylic resin as the component (A), which comprises the monomeric units of a (meth)acrylic acid ester of hydroxy bicyclo[3.1.1]heptanone unsubstituted or substituted by an alkyl group such as hydroxypinanone (meth)acrylate, optionally, in combination with the monomeric units derived from (meth)acrylic acid and/or tert-butyl (meth)acrylate in a molar fraction of 3:7 to 7:3.
摘要翻译：提出了用于制造精细电子器件的光刻图案化工艺中的新型化学增感正性光致抗蚀剂组合物，其能够赋予ArF准分子激光束具有高光敏性的具有良好正交交叉的图案化抗蚀剂层截面轮廓和高抗干蚀刻性，并且对基材表面具有良好的粘合性。虽然组合物包含（A）通过与酸相互作用而增加碱溶解度的成膜树脂成分和（B）辐射敏感的酸产生剂，但是本发明的最特征在于使用作为组分（A）的特定丙烯酸树脂，其包含未被取代或被烷基如羟基酮（甲基）丙烯酸酯取代的羟基双环[3.1.1]庚酮的（甲基）丙烯酸酯的单体单元，与来自（甲基）丙烯酸和/或（甲基）丙烯酸叔丁酯的单体单元组合，摩尔分数为3:7至7:3。

3. 发明授权

US06388101B1 Chemical-sensitization photoresist composition 有权
标题翻译：化学增感光刻胶组合物
公开(公告)号：US06388101B1
公开(公告)日：2002-05-14
申请号：US09562458
申请日：2000-05-02
申请人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
发明人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
IPC分类号： C07D30512
CPC分类号： C07D307/33 , G03F7/0392 , Y02P20/55
摘要： Proposed is a chemical-sensitization positive-working photoresist composition for photolithographic patterning in the manufacture of semiconductor devices having high transparency even to ultraviolet light of very short wavelength such as ArF excimer laser beams of 193 nm wavelength to exhibit high photosensitivity and capable of giving a patterned resist layer with high pattern resolution. The composition comprises (A) a resinous ingredient which is subject to an increase of the solubility in an aqueous alkaline developer solution in the presence of an acid and (B) a radiation-sensitive acid-generating compound. Characteristically, the resinous ingredient as the component (A) is a (meth)acrylic copolymer of which from 20% to 80% by moles of the monomeric units are derived from a (meth)acrylic acid ester of which the ester-forming group has a specific oxygen-containing heterocyclic ring structure.
摘要翻译：提出了一种用于制造半导体器件的化学增感正性光致抗蚀剂组合物，即使对于非常短波长的紫外光也具有高透明度，例如193nm波长的ArF准分子激光束，以显示高光敏性，并且能够给出具有高图案分辨率的图案化抗蚀剂层。组合物包含（A）在酸的存在下在碱性显影剂水溶液中溶解度增加的树脂成分和（B）辐射敏感的产酸化合物。特征在于，作为（A）成分的树脂成分是（甲基）丙烯酸系共聚物，20〜80摩尔％的单体单元衍生自成酯基的（甲基）丙烯酸酯特定的含氧杂环结构。

4. 发明授权

US06225476B1 Positive-working photoresist composition 有权
标题翻译：正光刻胶组合物
公开(公告)号：US06225476B1
公开(公告)日：2001-05-01
申请号：US09542952
申请日：2000-04-04
申请人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
发明人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
IPC分类号： C07D30733
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106 , Y10S430/111
摘要： Provided by the invention is a chemical-amplification positive-working photoresist composition used in the fine photolithographic patterning in the manufacturing process of semiconductor devices, which is suitable for the patterning light exposure with ArF excimer laser beams of very short wavelength by virtue of absence of aromatic structure in the ingredients of the composition. The composition comprises, as the film-forming resinous ingredient, an acrylic resin having unique monomeric units represented by the general formula &Brketopenst;CH2—CR1(—CO—O—CR2R3R4)&Brketclosest;, in which R1 is a hydrogen atom or a methyl group, R2 and R3 are each, independently from the other, an alkyl group having 1 to 4 carbon atoms and R4 is an alkoxycarbonyl group or a group derived from a molecule of a lactone compound or ketone compound by removing a hydrogen atom bonded to the carbon atom.
摘要翻译：本发明提供的是在半导体器件的制造过程中用于精细光刻图案化的化学放大正性光致抗蚀剂组合物，其适用于通过不存在非常短的波长的ArF准分子激光束来图案化曝光芳香结构在组成成分中。该组合物包含作为成膜树脂成分的丙烯酸树脂，其具有由通式为R 1为氢原子或甲基的单体单元表示的独特单体单元，R 2和R 3各自独立地为具有通过除去与碳原子键合的氢原子，R4是烷氧基羰基或衍生自内酯化合物或酮化合物的分子的基团。

5. 发明授权

US06087063A Positive-working photoresist composition 失效
标题翻译：正光刻胶组合物
公开(公告)号：US06087063A
公开(公告)日：2000-07-11
申请号：US102622
申请日：1998-06-23
申请人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
发明人： Hideo Hada , Kazufumi Sato , Hiroshi Komano
IPC分类号： G03F7/004 , G03F7/033 , G03F7/039 , H01L21/027
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106 , Y10S430/111
摘要： Provided by the invention is a chemical-amplification positive-working photoresist composition used in the fine photolithographic patterning in the manufacturing process of semiconductor devices, which is suitable for the patterning light exposure with ArF excimer laser beams of very short wavelength by virtue of absence of aromatic structure in the ingredients of the composition. The composition comprises, as the film-forming resinous ingredient, an acrylic resin having unique monomeric units represented by the general formula.brket open-st.CH.sub.2 --CR.sup.1 (--CO--O--CR.sup.2 R.sup.3 R.sup.4).brket close-st.,in which R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 and R.sup.3 are each, independently from the other, an alkyl group having 1 to 4 carbon atoms and R.sup.4 is an alkoxycarbonyl group or a group derived from a molecule of a lactone compound or ketone compound by removing a hydrogen atom bonded to the carbon atom.
摘要翻译：本发明提供的是在半导体器件的制造过程中用于精细光刻图案化的化学放大正性光致抗蚀剂组合物，其适用于通过不存在非常短的波长的ArF准分子激光束来图案化曝光芳香结构在组成成分中。该组合物包含作为成膜树脂成分的具有由通式+ 547 CH2-CR1（-CO-O-CR2R3R4）+548表示的独特单体单元的丙烯酸树脂，其中R 1是氢原子或甲基基团，R 2和R 3各自独立地为具有1至4个碳原子的烷基，R 4为烷氧基羰基或衍生自内酯化合物或酮化合物的分子的基团，通过除去与碳原子。

6. 发明授权

US06245930B1 Chemical-sensitization resist composition 有权
标题翻译：化学增感抗蚀剂组合物
公开(公告)号：US06245930B1
公开(公告)日：2001-06-12
申请号：US09317208
申请日：1999-05-24
申请人： Katsumi Oomori , Hideo Hada , Fumitake Kaneko , Mitsuru Sato , Kazufumi Sato , Toshimasa Nakayama
发明人： Katsumi Oomori , Hideo Hada , Fumitake Kaneko , Mitsuru Sato , Kazufumi Sato , Toshimasa Nakayama
IPC分类号： C07C25500
CPC分类号： G03F7/0045 , Y10S430/12 , Y10S430/122
摘要： Proposed is a novel chemical-sensitization resist composition capable of giving a positively or negatively patterned resist layer of excellent pattern resolution and cross sectional profile of the patterned resist layer with high sensitivity. Characteristically, the resist composition is formulated, as combined with a resinous ingredient which is subject to changes in the solubility behavior in an alkaline developer solution by interaction with an acid, with a specific oximesulfonate compound as the radiation-sensitive acid-generating agent represented by the general formula R1—C(CN)═N—O—SO2—R2, in which R1 is an inert organic group and R2 is an unsubstituted or substituted polycyclic monovalent hydrocarbon group selected from the group consisting of polycyclic aromatic hydrocarbon groups such as naphthyl and polycyclic non-aromatic hydrocarbon groups such as a terpene or camphor residue.
摘要翻译：提出了一种能够以高灵敏度赋予图案化抗蚀剂层优异图案分辨率和截面轮廓的正或负图案化抗蚀剂层的新型化学增感抗蚀剂组合物。特别地，将抗蚀剂组合物配制成与通过与酸相互作用而在碱性显影剂溶液中溶解度行为发生变化的树脂成分与特定的肟磺酸酯化合物作为辐射敏感性产酸剂， R 1为惰性有机基团，R2为未取代或取代的选自多环芳烃基如萘基和多环非芳族烃基如萜烯或樟脑残基的多环一价烃基。

7. 发明授权

US5976760A Chemical-sensitization resist composition 失效
标题翻译：化学增感抗蚀剂组合物
公开(公告)号：US5976760A
公开(公告)日：1999-11-02
申请号：US898105
申请日：1997-07-22
申请人： Katsumi Oomori , Hideo Hada , Fumitake Kaneko , Mitsuru Sato , Kazufumi Sato , Toshimasa Nakayama
发明人： Katsumi Oomori , Hideo Hada , Fumitake Kaneko , Mitsuru Sato , Kazufumi Sato , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/038 , G03F7/039 , H01L21/027 , G03C1/492
CPC分类号： G03F7/0045 , Y10S430/12 , Y10S430/122
摘要： Proposed is a novel chemical-sensitization resist composition capable of giving a positively or negatively patterned resist layer of excellent pattern resolution and cross sectional profile of the patterned resist layer with high sensitivity. Characteristically, the resist composition is formulated, as combined with a resinous ingredient which is subject to changes in the solubility behavior in an alkaline developer solution by interaction with an acid, with a specific oximesulfonate compound as the radiation-sensitive acid-generating agent represented by the general formulaR.sup.1 --C(CN).dbd.N--O--SO.sub.2 --R.sup.2,in which R.sup.1 is an inert organic group and R.sup.2 is an unsubstituted or substituted polycyclic monovalent hydrocarbon group selected from the group consisting of polycyclic aromatic hydrocarbon groups such as naphthyl and polycyclic non-aromatic hydrocarbon groups such as a terpene or camphor residue.
摘要翻译：提出了一种能够以高灵敏度赋予图案化抗蚀剂层优异图案分辨率和截面轮廓的正或负图案化抗蚀剂层的新型化学增感抗蚀剂组合物。特别地，将抗蚀剂组合物配制成与通过与酸相互作用而在碱性显影剂溶液中溶解度行为发生变化的树脂成分与特定的肟磺酸酯化合物作为辐射敏感性产酸剂，通式为R1-C（CN）= NO-SO2-R2，其中R1为惰性有机基团，R2为未取代或取代的多环一价烃基，选自多环芳烃基如萘基和多环非芳族烃基如萜烯或樟脑残基。

8. 发明授权

US5736296A Positive resist composition comprising a mixture of two polyhydroxystyrenes having different acid cleavable groups and an acid generating compound 失效
标题翻译：包含两种具有不同的酸可分解基团的聚羟基苯乙烯和产酸化合物的混合物的正性抗蚀剂组合物
公开(公告)号：US5736296A
公开(公告)日：1998-04-07
申请号：US625931
申请日：1996-04-01
申请人： Mitsuru Sato , Kazuyuki Nitta , Akiyoshi Yamazaki , Etsuko Iguchi , Yoshika Sakai , Kazufumi Sato , Toshimasa Nakayama
发明人： Mitsuru Sato , Kazuyuki Nitta , Akiyoshi Yamazaki , Etsuko Iguchi , Yoshika Sakai , Kazufumi Sato , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/039
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106
摘要： Disclosed is an improved, chemically-amplifying positive resist composition for radiations, especially UV rays, deep-UV rays, excimer laser beams, X-rays, electron beams. The composition comprises (A) a resin component whose solubility in an alkaline aqueous solution is increased by the action of acids, (B) a compound which generates an acid when exposed to radiations, and (A) a resin component, (B) an acid-generating agent and (C) an organic carboxylic acid compound, in which said resin component (A) is a mixture comprising (a) a polyhydroxystyrene where from 10 to 60 mol % of the hydroxyl groups have been substituted by residues of a general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group, R.sup.2 represents a methyl group or an ethyl group, and R.sup.3 represents a lower alkyl group having 1 to 4 carbon atoms; and (b) a polyhydroxystyrene where from 10 to 60 mol % of the hydroxyl groups have been substituted by tert-butoxycarbonyloxy groups. The composition has a high sensitivity, a high resolution, high heat resistance, good width characteristic in focus depth and good post-exposure storage stability, has good storage stability as a resist solution, and gives resist patterns with good profiles, without depending on the substrate to which it is applied. The composition is useful for forming fine patterns in producing ultra-LSIs.
摘要翻译：公开了用于辐射，特别是紫外线，深紫外线，准分子激光束，X射线，电子束的改进的化学增幅正性抗蚀剂组合物。该组合物包含（A）通过酸的作用在碱性水溶液中的溶解度增加的树脂成分，（B）暴露于辐射时产生酸的化合物，（A）树脂成分，（B）酸性发生剂和（C）有机羧酸化合物，其中所述树脂组分（A）是包含（a）多羟基苯乙烯的混合物，其中10至60mol％的羟基已被一般的残基取代式（I）：其中R 1表示氢原子或甲基，R 2表示甲基或乙基，R 3表示碳原子数1〜4的低级烷基。和（b）聚羟基苯乙烯，其中10至60摩尔％的羟基已被叔丁氧羰基氧基取代。该组合物具有高灵敏度，高分辨率，高耐热性，聚焦深度的良好宽度特性和良好的曝光后储存稳定性，作为抗蚀剂溶液具有良好的储存稳定性，并且具有良好外形的抗蚀剂图案，而不依赖于底物。该组合物可用于在制造超LSI时形成精细图案。

9. 发明授权

US6159652A Positive resist composition 失效
标题翻译：正抗蚀剂组成
公开(公告)号：US6159652A
公开(公告)日：2000-12-12
申请号：US20408
申请日：1998-02-09
申请人： Mitsuru Sato , Kazuyuki Nitta , Akiyoshi Yamazaki , Etsuko Iguchi , Yoshika Sakai , Kazufumi Sato , Toshimasa Nakayama
发明人： Mitsuru Sato , Kazuyuki Nitta , Akiyoshi Yamazaki , Etsuko Iguchi , Yoshika Sakai , Kazufumi Sato , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/039
CPC分类号： G03F7/039 , G03F7/0045 , Y10S430/106
摘要： Disclosed is an improved, chemically-amplifying positive resist composition for radiations, especially UV rays, deep-UV rays, excimer laser beams, X-rays, electron beams. The composition comprises (A) a resin component whose solubility in an alkaline aqueous solution is increased by the action of acids, (B) a compound which generates an acid when exposed to radiations, and (A) a resin component, (B) an acid-generating agent and (C) an organic carboxylic acid compound, in which said resin component (A) is a mixture comprising (a) a polyhydroxystyrene where from 10 to 60 mol % of the hydroxyl groups have been substituted by residues of a general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group, R.sup.2 represents a methyl group or an ethyl group, and R.sup.3 represents a lower alkyl group having 1 to 4 carbon atoms;and (b) a polyhydroxystyrene where from 10 to 60 mol % of the hydroxyl groups have been substituted by tert-butoxy-carbonyloxy groups. The composition has a high sensitivity, a high resolution, high heat resistance, good width characteristic in focus depth and good post-exposure storage stability, has good storage stability as a resist solution, and gives resist patterns with good profiles, without depending on the substrate to which it is applied. The composition is useful for forming fine patterns in producing ultra-LSIs.
摘要翻译：公开了用于辐射，特别是紫外线，深紫外线，准分子激光束，X射线，电子束的改进的化学增幅正性抗蚀剂组合物。该组合物包含（A）通过酸的作用在碱性水溶液中的溶解度增加的树脂成分，（B）暴露于辐射时产生酸的化合物，（A）树脂成分，（B）酸性发生剂和（C）有机羧酸化合物，其中所述树脂组分（A）是包含（a）多羟基苯乙烯的混合物，其中10至60mol％的羟基已被一般的残基取代式（I）：其中R1表示氢原子或甲基，R2表示甲基或乙基，R3表示碳原子数1〜4的低级烷基。和（b）聚羟基苯乙烯，其中10至60摩尔％的羟基已被叔丁氧基 - 羰基氧基取代。该组合物具有高灵敏度，高分辨率，高耐热性，聚焦深度的良好宽度特性和良好的曝光后储存稳定性，作为抗蚀剂溶液具有良好的储存稳定性，并且具有良好外形的抗蚀剂图案，而不依赖于底物。该组合物可用于在制造超LSI时形成精细图案。

10. 发明授权

US5908730A Chemical-sensitization photoresist composition 失效
标题翻译：化学增感光刻胶组合物
公开(公告)号：US5908730A
公开(公告)日：1999-06-01
申请号：US898320
申请日：1997-07-22
申请人： Kazuyuki Nitta , Kazufumi Sato , Akiyoshi Yamazaki , Yoshika Sakai , Toshimasa Nakayama
发明人： Kazuyuki Nitta , Kazufumi Sato , Akiyoshi Yamazaki , Yoshika Sakai , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/038 , G03F7/039
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039
摘要： Proposed is a positive- or negative-working chemical-sensitization photoresist composition having advantages in respect of the contrast and resolution of patterning, photosensitivity and cross sectional profile of the patterned resist layer as well as in respect of stability of the latent image formed by pattern-wise exposure to light before post-exposure baking treatment. The composition comprises: (A) 100 parts by weight of a film-forming resinous ingredient which causes a change, i.e. increase or decrease, of solubility in an aqueous alkaline solution by the interaction with an acid; and (B) from 0.5 to 20 parts by weight of a radiation-sensitive acid-generating agent which is a diazomethane compound represented by the general formulaR.sup.1 --SO.sub.2 --C(.dbd.N.sub.2)--SO.sub.2 --R.sup.2,in which R.sup.1 and R.sup.2 are each, independently from the other, a monovalent cyclic group substituted on the cyclic nucleus by an acid-dissociable group such as a tert-butoxycarbonyl and acetal groups.
摘要翻译：提出了一种正性或负性的化学增感光致抗蚀剂组合物，其在图案化抗蚀剂层的图案的对比度和分辨率，光敏性和横截面轮廓方面以及关于通过图案形成的潜像的稳定性方面具有优势在曝光前烘烤处理下曝光。该组合物包含：（A）100重量份成膜树脂成分，其通过与酸的相互作用而引起在碱性水溶液中的溶解度的改变，即增加或减少; 和（B）0.5〜20重量份的辐射敏感性酸产生剂，其为通式R 1 -SO 2 -C（= N 2）-SO 2 -R 2表示的重氮甲烷化合物，其中R 1和R 2为各自独立地是通过酸解离基团如叔丁氧基羰基和缩醛基在环状核上取代的一价环状基团。

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