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公开(公告)号：US5800964A
公开(公告)日：1998-09-01
申请号：US717779
申请日：1996-09-24
申请人： Mitsuru Sato , Kazuyuki Nitta , Hideo Hada , Tatsuya Hashiguchi , Hiroshi Komano , Toshimasa Nakayama
发明人： Mitsuru Sato , Kazuyuki Nitta , Hideo Hada , Tatsuya Hashiguchi , Hiroshi Komano , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/038 , G03F7/039 , H01L21/027
CPC分类号： G03F7/0045 , Y10S430/12 , Y10S430/122
摘要： Disclosed is a novel and improved photoresist composition which comprises: (A) a film-forming resinous compound which is, in the presence of an acid, subject to a change in the solubility in an alkaline solution; and (B) an acid-generating agent capable of releasing an acid by the exposure to actinic rays which is an oxime sulfonate compound represented by the general formula NC--CR.sup.1 .dbd.N--O--SO.sub.2 --R.sup.2, in which R.sup.1 and R.sup.2 are, each independently from the other, an unsubstituted or halogen-substituted monovalent aliphatic hydrocarbon group, e.g., alkyl, cycloalkyl, alkenyl and cycloalkenyl groups. By virtue of the non-aromatic nature of the component (B) as well as good solubility thereof in organic solvents and high acid strength of the acid released therefrom, the composition is highly transparent to deep ultraviolet light even when the content of the component (B) is relatively large and the photosensitivity of the composition is very high so that the photoresist composition is capable of giving a patterned resist layer having excellent characteristics.
摘要翻译： 公开了一种新颖且改进的光致抗蚀剂组合物，其包含：（A）在酸存在下，在碱溶液中溶解度变化的成膜树脂化合物; 和（B）能够通过暴露于由通式NC-CR1 = NO-SO2-R2表示的肟磺酸盐化合物的光化射线释放酸的酸产生剂，其中R 1和R 2各自独立地为 另一个，未取代或卤素取代的一价脂族烃基，例如烷基，环烷基，烯基和环烯基。 由于组分（B）的非芳香性质以及其在有机溶剂中的良好溶解性和从其释放的酸的高酸强度，组合物对于深紫外光是高度透明的，即使组分（ B）相对较大并且组合物的光敏性非常高，使得光致抗蚀剂组合物能够提供具有优异特性的图案化抗蚀剂层。
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公开(公告)号：US5714625A
公开(公告)日：1998-02-03
申请号：US712884
申请日：1996-09-12
IPC分类号： G03F7/004 , C07C309/65 , C07C309/66 , C07C255/35
CPC分类号： C07C309/65 , C07C309/66 , C07C2101/10 , C07C2101/16
摘要： Disclosed is a class of novel cyanooxime sulfonate compounds represented by the general formula NC--CR.sup.1 .dbd.N--O--SO.sub.2 --R.sup.2, in which R.sup.1 and R.sup.2 are, each independently from the other, an unsubstituted or halogen-substituted monovalent aliphatic hydrocarbon group selected from the group consisting of alkyl, cycloalkyl, alkenyl and cycloalkenyl groups. The group R.sup.1 is preferably a cycloalkenyl group, e.g. 1-cyclopentenyl or 1-cyclohexenyl group, and R.sup.2 is preferably a lower alkyl group having 1 to 4 carbon atoms. The compound releases an acid by the irradiation with ultraviolet light and is useful as an acid generating agent in an acid-sensitive photoresist composition. By virtue of the high transparency of the compound to ultraviolet, high acid strength of the acid generated therefrom and good solubility of the compound in organic solvents, the photoresist composition compounded with the compound as an acid generating agent is imparted with high sensitivity to ultraviolet and capable of giving a patterned resist layer having excellent characteristics.
摘要翻译： 公开了一类由通式NC-CR1 = NO-SO2-R2表示的新型氰基肟磺酸盐化合物，其中R 1和R 2各自独立地为未取代或卤素取代的一价脂族烃基，其选自 由烷基，环烷基，烯基和环烯基组成的组。 基团R1优选为环烯基，例如 1-环戊烯基或1-环己烯基，R2优选为具有1〜4个碳原子的低级烷基。 该化合物通过紫外线照射而释放酸，并且可用作酸敏感光刻胶组合物中的酸产生剂。 由于化合物对紫外线的高透明度，由其产生的酸的高酸强度和化合物在有机溶剂中的良好溶解性，与作为酸产生剂的化合物混合的光致抗蚀剂组合物赋予对紫外线的高灵敏度， 能够赋予具有优异特性的图案化抗蚀剂层。
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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。
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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。
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公开(公告)号：US5892095A
公开(公告)日：1999-04-06
申请号：US791814
申请日：1997-01-30
申请人： Hideo Hada , Hiroshi Komano , Toshimasa Nakayama
发明人： Hideo Hada , Hiroshi Komano , Toshimasa Nakayama
IPC分类号： C07C307/02 , C07C309/65 , C07C309/66 , C07C309/73 , G03F7/004 , G03F7/038 , G03F7/039 , H01L21/027 , C07C255/00 , G03F5/16 , G03F7/022
CPC分类号： C07C309/66 , C07C309/65 , C07C309/73 , G03F7/0045
摘要： Disclosed is a novel positive-working or negative-working chemical-sensitization photoresist composition useful in the photolithographic patterning works for the manufacture of electronic devices. The photoresist composition is characterized by a unique acid-generating agent capable of releasing an acid by the pattern-wise exposure of the resist layer to actinic rays so as to increase or decrease the solubility of the resist layer in an aqueous alkaline developer solution. The acid-generating agent proposed is a novel cyano group-containing oxime sulfonate di- or triester compound represented by the general formulaA�C(CN).dbd.N--O--SO.sub.2 --R!.sub.n,in which each R is, independently from the others, an unsubstituted or substituted monovalent hydrocarbon group such as alkyl groups, A is a divalent or tervalent organic group or, preferably, phenylene group and the subscript n is 2, when A is a divalent group, or 3, when A is a tervalent group or, preferably 2. Since more than one of sulfonic acid molecules are released from one molecule of the sulfonate compound by the exposure to actinic rays, the chemical-sensitization photoresist composition exhibits high photosensitivity.
摘要翻译： 公开了一种用于制造电子器件的光刻图案化工艺中的新型正性或负性化学增感光致抗蚀剂组合物。 光致抗蚀剂组合物的特征在于能够通过抗蚀剂层与光化射线的图案曝光而释放酸的独特的酸产生剂，从而增加或降低抗蚀剂层在碱性显影剂水溶液中的溶解度。 所提出的酸产生剂是由通式A [C（CN）= NO-SO 2 -R] n表示的新的含氰基的肟磺酸酯二酯或三酯化合物，其中每个R独立地为 未取代或取代的一价烃基如烷基，A是二价或三价有机基团，或优选亚苯基，下标n为2，当A为二价基团时，或3，当A为三价基团或 ，优选2.由于通过暴露于光化射线，一个以上的磺酸分子从一分子的磺酸酯化合物中释放出来，化学增感光致抗蚀剂组合物表现出高的光敏性。
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公开(公告)号：US06329126B1
公开(公告)日：2001-12-11
申请号：US08339340
申请日：1994-11-14
IPC分类号： G03F732
CPC分类号： G03F7/322
摘要： Disclosed is a novel aqueous developer solution used in the development treatment of an actinic ray-sensitive resist for the manufacture of, for example, semiconductor devices, which is capable of giving a patterned resist layer free from the troubles of film residue or scum deposition in any finest patterning. The developer solution contains, in addition to a nitrogen-containing organic basic compound, e.g., tetramethyl ammonium hydroxide, dissolved in an aqueous medium as the solvent, an anionic surface active agent which is a diphenyl ether compound having at least one ammonium sulfonate group, such as an ammonium alkyl diphenylether sulfonate, in a concentration of 0.05 to 5% by weight.
摘要翻译： 公开了一种用于显影处理用于制造例如半导体器件的光化抗敏抗蚀剂的新型水性显影剂溶液，其能够提供没有膜残留物或浮渣沉积问题的图案化抗蚀剂层 任何最好的图案。 除了溶解在作为溶剂的水性介质中的含氮有机碱性化合物例如四甲基氢氧化铵之外，显影剂溶液还含有具有至少一个磺酸铵基团的二苯基醚化合物的阴离子表面活性剂， 例如烷基二苯基醚磺酸铵，其浓度为0.05-5重量％。
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公开(公告)号：US5543268A
公开(公告)日：1996-08-06
申请号：US231877
申请日：1994-04-22
IPC分类号： G03F7/32
CPC分类号： G03F7/322
摘要： Disclosed is a novel aqueous developer solution used in the development treatment of an actinic ray-sensitive resist for the manufacture of, for example, semiconductor devices, which is capable of giving a patterned resist layer free from the troubles of film residue or scum deposition in any finest patterning. The developer solution contains, in addition to a nitrogen-containing organic basic compound, e.g., tetramethyl ammonium hydroxide, dissolved in an aqueous medium as the solvent, an anionic surface active agent which is a diphenyl ether compound having at least one ammonium sulfonate group, such as an ammonium alkyl diphenylether sulfonate, in a concentration of 0.05 to 5% by weight.
摘要翻译： 公开了一种用于显影处理用于制造例如半导体器件的光化抗敏抗蚀剂的新型水性显影剂溶液，其能够提供没有膜残留物或浮渣沉积问题的图案化抗蚀剂层 任何最好的图案。 除了溶解在作为溶剂的水性介质中的含氮有机碱性化合物例如四甲基氢氧化铵之外，显影剂溶液还含有具有至少一个磺酸铵基团的二苯基醚化合物的阴离子表面活性剂， 例如烷基二苯基醚磺酸铵，其浓度为0.05-5重量％。
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8.发明授权Composition for forming antireflective coating film and method for forming resist pattern using same 失效用于形成抗反射涂膜的组合物和使用其形成抗蚀剂图案的方法公开(公告)号：US06268108B1
公开(公告)日：2001-07-31
申请号：US09116460
申请日：1998-07-16
IPC分类号： G03F7004
CPC分类号： G03F7/091
摘要： The present invention provides a composition for forming an antireflective coating film which is not liable to intermixing between the resist composition layer and the antireflective coating layer and a method for forming a resist pattern having an excellent dimensional accuracy and section shape. The composition consists of (A) a compound which produces an acid upon irradiation with actinic rays, (B) a compound which undergoes crosslinking reaction in the presence of an acid, (C) a dye and (D) an organic solvent. The method for forming a resist pattern comprises applying the composition for forming an antireflective coating film to a semiconductor substrate, drying the composition coated, irradiating the entire surface of the coated material with actinic rays so that it undergoes crosslinking reaction to form an antireflective coating film thereon, applying a resist composition to the antireflective coating film, drying the coated material, and then subjecting the coated material to lithographic processing to form a resist pattern thereon.
摘要翻译： 本发明提供了一种用于形成不易于在抗蚀剂组合物层和抗反射涂层之间混合的抗反射涂膜的组合物和形成具有优异的尺寸精度和截面形状的抗蚀剂图案的方法。 组合物由（A）在光化射线照射时产生酸的化合物，（B）在酸存在下进行交联反应的化合物，（C）染料和（D）有机溶剂。 形成抗蚀剂图案的方法包括将用于形成抗反射涂膜的组合物施加到半导体衬底上，干燥涂覆的组合物，用光化射线照射涂覆材料的整个表面，使其经历交联反应以形成抗反射涂膜 在其上涂布抗蚀剂组合物到抗反射涂膜上，干燥涂覆的材料，然后对涂覆材料进行光刻处理以在其上形成抗蚀剂图案。
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9.发明授权Liquid coating composition for use in forming antireflective film and photoresist material using said antireflective film 有权用于使用所述抗反射膜形成抗反射膜和光致抗蚀剂材料的液体涂料组合物
公开(公告)号：US06136505A
公开(公告)日：2000-10-24
申请号：US330001
申请日：1999-06-11
IPC分类号： G03F7/004 , G03F7/09 , G03F7/11 , H01L21/027
CPC分类号： G03F7/091
摘要： Disclosed herein is a liquid coating composition for use in forming an antireflective film comprising a mixture of a cyclic perfluoroalkyl polyether and a chain perfluoroalkyl polyether in a ratio of from 3:10 to 10:1 by weight, and a fluorocarbon organic solvent. Disclosed also herein is a photoresist material consisting of a photoresist layer and said antireflective film formed thereon using said liquid coating composition. The antireflective film remarkably reduces the standing-wave effect especially in the case where the photoresist layer of chemically amplified type is used. The antireflective film also has good film quality and film removability.
摘要翻译： 本文公开了一种用于形成抗反射膜的液体涂料组合物，其包含按重量比计为3:10至10:1的环状全氟烷基聚醚和链全氟烷基聚醚的混合物，以及氟碳有机溶剂。 此处还公开了由光致抗蚀剂层和在其上使用所述液体涂料组合物形成的所述抗反射膜组成的光致抗蚀剂材料。 抗反射膜特别是在使用化学放大型光致抗蚀剂层的情况下，显着地降低了驻波效应。 抗反射膜也具有良好的膜质量和膜去除性。
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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。
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