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公开(公告)号：US5973187A
公开(公告)日：1999-10-26
申请号：US179818
申请日：1998-10-28
申请人： Hideo Hada , Yoshiki Sugeta , Hiroyuki Yamazaki , Hiroshi Komano
发明人： Hideo Hada , Yoshiki Sugeta , Hiroyuki Yamazaki , Hiroshi Komano
IPC分类号： C07C307/02 , C07C309/65 , C07C309/66 , C07C309/73 , G03F7/004 , G03F7/038 , G03F7/039 , H01L21/027 , C07C255/00
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：US6063953A
公开(公告)日：2000-05-16
申请号：US236612
申请日：1999-01-26
申请人： Hideo Hada , Hiroyuki Yamazaki , Yoshiki Sugeta , Hiroshi Komano
发明人： Hideo Hada , Hiroyuki Yamazaki , Yoshiki Sugeta , Hiroshi Komano
IPC分类号： C09K3/00 , G03F7/004 , G03F7/033 , G03F7/038 , G03F7/039 , H01L21/027 , C07C255/07
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/12 , Y10S430/122
摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.
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公开(公告)号：US6022666A
公开(公告)日：2000-02-08
申请号：US236567
申请日：1999-01-26
申请人： Hideo Hada , Hiroyuki Yamazaki , Yoshiki Sugeta , Hiroshi Komano
发明人： Hideo Hada , Hiroyuki Yamazaki , Yoshiki Sugeta , Hiroshi Komano
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/12 , Y10S430/122
摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.
摘要翻译： 公开了能够赋予高分辨率的高耐热图案化抗蚀剂层的新型高灵敏度正负工作化学增感光致抗蚀剂组合物，而不受驻波的影响，具有非常正交的横截面轮廓。 该组合物通过用光化射线照射作为酸产生剂含有特定的氰基取代的肟磺酸酯化合物，例如α-（甲基磺酰氧基亚氨基）-4-甲氧基苄基氰化物。 当成膜树脂成分具有使重均分子量与数均分子量的比例不超过3.5的分子量分布时，通过使用该特定酸产生剂获得的优点是显着的。
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公开(公告)号：US5990338A
公开(公告)日：1999-11-23
申请号：US179817
申请日：1998-10-28
申请人： Hideo Hada , Yoshiki Sugeta , Hiroyuki Yamazaki , Hiroshi Komano
发明人： Hideo Hada , Yoshiki Sugeta , Hiroyuki Yamazaki , Hiroshi Komano
IPC分类号： C07C307/02 , C07C309/65 , C07C309/66 , C07C309/73 , G03F7/004 , G03F7/038 , G03F7/039 , H01L21/027 , C07C255/00
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：US5902713A
公开(公告)日：1999-05-11
申请号：US762920
申请日：1996-12-10
CPC分类号： G03F7/038 , G03F7/0045 , G03F7/039 , Y10S430/12 , Y10S430/122
摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.
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6.发明授权Negative-working chemical-sensitization photoresist composition comprising oxime sulfonate compounds 失效包含肟磺酸盐化合物的负性化学增感光致抗蚀剂组合物
公开(公告)号：US5928837A
公开(公告)日：1999-07-27
申请号：US987023
申请日：1997-12-09
申请人： Mitsuru Sato , Kiyoshi Ishikawa , Yoshiki Sugeta , Hiroyuki Yamazaki , Toshikazu Tachikawa , Hiroshi Komano
发明人： Mitsuru Sato , Kiyoshi Ishikawa , Yoshiki Sugeta , Hiroyuki Yamazaki , Toshikazu Tachikawa , Hiroshi Komano
IPC分类号： G03F7/004 , G03F7/038 , H01L21/027 , G03C1/492
CPC分类号： G03F7/038 , G03F7/0045 , Y10S430/12 , Y10S430/122
摘要： Proposed is a novel negative-working chemical-sensitization photoresist composition used in the photolithographic patterning work for the manufacture of semiconductor devices and the like and capable of giving a patterned resist layer with high sensitivity and pattern resolution as well as excellent heat resistance and excellently orthogonal cross sectional profile of the patterned resist layer. The composition comprises, as a uniform solution:(A) 100 parts by weight of an alkali-soluble resin which is a polyhydroxystyrene-based resin having a weight-average molecular weight of at least 2000;(B) from 3 to 70 parts by weight of an acid-crosslinkable compound which is an amino resin having hydroxyalkyl and/or alkoxyalkyl groups;(C) from 0.5 to 30 parts by weight of a radiation-sensitive acid-generating compound selected from several types of specific oximesulfonate compounds; and(D) from 0.5 to 10 parts by weight of a phenolic compound, such as benzophenone compounds, having at least four hydroxyl groups in a molecule and a molecular weight smaller than 2000.
摘要翻译： 提出了用于制造半导体器件等的光刻图案化工作中的新颖的负极化学增感光致抗蚀剂组合物，并且能够提供具有高灵敏度和图案分辨率的图案化抗蚀剂层以及优异的耐热性和良好的正交 图案化抗蚀剂层的横截面轮廓。 该组合物包含作为均匀溶液：（A）100重量份作为重均分子量为至少2000的聚羟基苯乙烯类树脂的碱溶性树脂; （B）3〜70重量份作为具有羟烷基和/或烷氧基烷基的氨基树脂的酸交联性化合物; （C）0.5〜30重量份选自几种特定肟磺酸酯化合物的辐射敏感产酸化合物; 和（D）0.5〜10重量份在分子中具有至少四个羟基并且分子量小于2000的酚类化合物，例如二苯甲酮化合物。
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7.发明授权Chemical-amplification-type negative resist composition and method for forming negative resist pattern 失效化学放大型负型抗蚀剂组合物及其形成负型抗蚀剂图案的方法
公开(公告)号：US5955241A
公开(公告)日：1999-09-21
申请号：US956792
申请日：1997-10-23
CPC分类号： G03F7/038 , G03F7/0045 , Y10S430/12 , Y10S430/122
摘要： The present invention provides a chemical-amplification-type negative resist composition and a method for forming a negative resist pattern using the same. The chemical-amplification-type negative resist composition comprises (A) an alkali-soluble resin, (B) an acid-generating agent, and (C) a compound capable of causing crosslinking reaction in the presence of an acid, wherein the ingredient (A) is a mixture comprising (i) a copolymer which comprises constitutional repeating units of a hydroxystyrene type, has a weight average molecular weight of 2,000 to 4,000, and has a ratio of the weight average molecular weight to the number average molecular weight falling within 1.0 to 2.0; and (ii) a hydroxystyrene homopolymer, and wherein the dissolution rate of the ingredient (A) at 23.degree. C. in a 2.38% by weight tetramethylammonium hydroxide aqueous solution falls within 80 to 300 nm/s.
摘要翻译： 本发明提供化学放大型负光刻胶组合物和使用其形成负光刻胶图案的方法。 化学增幅型负性抗蚀剂组合物包含（A）碱溶性树脂，（B）酸产生剂和（C）在酸存在下能够引起交联反应的化合物，其中成分（ A）是包含（i）包含羟基苯乙烯型结构重复单元的共聚物，其重均分子量为2,000至4,000的共聚物，并且其重均分子量与数均分子量的比率 1.0〜2.0; 和（ii）羟基苯乙烯均聚物，并且其中成分（A）在23℃在2.38重量％四甲基氢氧化铵水溶液中的溶解速率为80-300nm / s。
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公开(公告)号：US20080145539A1
公开(公告)日：2008-06-19
申请号：US12068710
申请日：2008-02-11
IPC分类号： B05D3/02
CPC分类号： G03F7/40 , H01L21/0273
摘要： It is disclosed a method of forming fine patterns comprising: subjecting a substrate having photoresist patterns to a hydrophilic treatment, covering the substrate having photoresist patterns with an over-coating agent for forming fine patterns, applying heat treatment to cause thermal shrinkage of the over-coating agent so that the spacing between adjacent photoresist patterns is lessened by the resulting thermal shrinking action, and removing the over-coating agent substantially completely.
摘要翻译： 公开了一种形成精细图案的方法，包括：对具有光致抗蚀剂图案的基板进行亲水处理，用用于形成精细图案的过涂层覆盖具有光致抗蚀剂图案的基板，进行热处理以引起过热， 使得相邻的光致抗蚀剂图案之间的间隔由于所得的热收缩作用而减轻，并且基本上完全除去覆盖剂。
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9.发明授权Agent for forming coating for narrowing patterns and method for forming fine pattern using the same 有权用于形成缩小图案的涂层剂和使用其形成精细图案的方法公开(公告)号：US07235345B2
公开(公告)日：2007-06-26
申请号：US10471772
申请日：2002-11-05
IPC分类号： G03C5/00
CPC分类号： G03F7/40
摘要： It is disclosed an over-coating agent for forming fine patterns which is applied to cover a substrate having photoresist patterns thereon and allowed to shrink under heat so that the spacing between the adjacent photoresist patterns is lessened, further characterized by containing a water-soluble polymer and a surfactant. Also disclosed is a method of forming fine-line patterns using the over-coating agent. According to the invention, one can obtain fine-line patterns which exhibit good profiles while satisfying the characteristics required of semiconductor devices, being excellent in controlling the dimension of patterns.
摘要翻译： 公开了一种用于形成精细图案的过涂层剂，其用于覆盖其上具有光刻胶图案的基材并在加热下使其收缩，使得相邻的光致抗蚀剂图案之间的间隔减小，其特征还在于含有水溶性聚合物 和表面活性剂。 还公开了使用过涂层剂形成细线图案的方法。 根据本发明，可以获得在满足半导体器件所要求的特性的情况下具有良好外形的精细线图形，并且控制图案的尺寸是优异的。
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10.发明申请公开(公告)号：US20060258809A1
公开(公告)日：2006-11-16
申请号：US11487330
申请日：2006-07-17
CPC分类号： G03F7/40 , G03F7/0035
摘要： It is disclosed an over-coating agent for forming fine-line patterns which is applied to cover a substrate having thereon photoresist patterns and allowed to shrink under heat so that the spacing between adjacent photoresist patterns is lessened, with the applied film of the over-coating agent being removed substantially completely to form or define fine trace patterns, further characterized by containing a copolymer or a mixture of polyvinyl alcohol with a water-soluble polymer other than polyvinyl alcohol. Also disclosed is a method of forming fine-line patterns using the over-coating agent. According to the invention, one can effectively increase the shrinkage amount (the amount of heat shrinking) of the agent, thereby achieving a remarkably improved effect of forming or defining fine-line patterns and which also present satisfactory profiles and meet the characteristics required of today's semiconductor devices.
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