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1. 发明授权

US5434031A Positive-working naphthoquinone diazide photoresist composition containing specific hydroxy compound additive 失效
标题翻译：含有特定羟基化合物添加剂的正性萘醌二叠氮光致抗蚀剂组合物
公开(公告)号：US5434031A
公开(公告)日：1995-07-18
申请号：US153100
申请日：1993-11-17
申请人： Taku Nakao , Remi Numata , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Taku Nakao , Remi Numata , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03C1/61 , G03F7/022 , G03F7/023
CPC分类号： G03F7/0226 , G03C1/61
摘要： Disclosed is a positive-working photoresist composition suitable for use in the photolithographic fine patterning work in the manufacture of electronic devices such as VLSIs. The composition comprises, in addition to an alkali-soluble novolac resin as a film-forming ingredient and an esterification product of naphthoquinone-1,2-diazide sulfonic acid as a photosensitive ingredient, a unique additive compound which is an alkyl or aralkyl ester of 2-hydroxy benzoic acid, such as benzyl salicylate, or a phenol compound substituted at least one alkyl group such as 2-tert-butyl-4-methyl phenol. By virtue of the addition of this unique additive, the inventive photoresist composition exhibits an excellent performance of suppressing the standing wave effect in addition to the excellent photosensitivity, resolving power and depth of focusing in the patterning exposure to light as well as good heat resistance of the patterned resist layer.
摘要翻译：公开了一种适用于制造诸如VLSI的电子设备的光刻精细图案化工作中的正性光致抗蚀剂组合物。除了作为成膜成分的碱溶性酚醛清漆树脂和萘醌-1,2-二叠氮磺酸作为感光成分的酯化产物之外，组合物还包含作为感光成分的独特的添加剂化合物，其为烷基或芳烷基酯 2-羟基苯甲酸，如水杨酸苄酯，或取代至少一个烷基的酚化合物如2-叔丁基-4-甲基苯酚。通过添加这种独特的添加剂，本发明的光致抗蚀剂组合物除了在图案曝光中具有优异的光敏性，分辨能力和聚焦深度以及良好的耐热性外，还表现出优异的抑制驻波效应的性能图案化的抗蚀剂层。

2. 发明授权

US5478692A Positive-working naphthoquinone diazide sulfonic acid ester photoresist composition containing 4,4'-bis(dialkylamino)benzophenone 失效
标题翻译：含有4,4'-双（二烷基氨基）二苯甲酮的正性萘醌二叠氮磺酸酯光致抗蚀剂组合物
公开(公告)号：US5478692A
公开(公告)日：1995-12-26
申请号：US350128
申请日：1994-11-29
申请人： Kousuke Doi , Taku Nakao , Remi Numata , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Kousuke Doi , Taku Nakao , Remi Numata , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/022 , G03F7/031 , H01L21/027 , G03F7/023
CPC分类号： G03F7/0226
摘要： Proposed is a novel positive-working photoresist composition suitable for use in the fine patterning works in the manufacture of electronic devices and capable of exhibiting excellent performance with high resolution, high sensitivity, wide range of focusing depth, large exposure dose latitude and other characteristics. The photoresist composition is formulated, in addition to the basic ingredients of an alkali-soluble novolac resin as a film-forming agent and photosensitive ingredient such as an ester of naphthoquinone-1,2-diazide sulfonic acid and a polyhydroxy compound, with a limited amount of 4,4'-bis(dialkylamino) benzophenone, e.g., 4,4'-bis(diethylamino) benzophenone, preferably, in combination with a polyhydroxy compound such as 4,6-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]-1,3-dihydroxy phenol.
摘要翻译：提出了一种新型正性光致抗蚀剂组合物，适用于电子器件制造中的精细图案化工作，能够以高分辨率，高灵敏度，宽范围的聚焦深度，较大的曝光剂量纬度等特性表现出优异的性能。光致抗蚀剂组合物除了作为成膜剂的碱溶性酚醛清漆树脂的基本成分和萘醌-1,2-二叠氮磺酸和多羟基化合物的酯等感光成分以外，配合有限制 4,4'-双（二烷基氨基）二苯甲酮的量，例如4,4'-双（二乙基氨基）二苯甲酮，优选与多羟基化合物如4,6-双[1-甲基-1-（4 - 羟基苯基）乙基] -1,3-二羟基苯酚。

3. 发明授权

US5501936A Positive-working quinonediazide photoresist composition containing a cyclohexyl-substituted triphenylmethane compound 失效
标题翻译：含有环己基取代的三苯基甲烷化合物的正性醌二叠氮化物光致抗蚀剂组合物
公开(公告)号：US5501936A
公开(公告)日：1996-03-26
申请号：US362857
申请日：1994-12-23
申请人： Hiroshi Hosoda , Remi Numata , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Hiroshi Hosoda , Remi Numata , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/004 , G03F7/022 , G03F7/039 , H01L21/027 , G03F7/023
CPC分类号： G03F7/0226
摘要： An improved positive-working photoresist composition useful in the fine patterning work of a resist layer is proposed which is capable of giving a patterned resist layer having excellent resolution, heat resistance and orthogonality of the cross sectional profile of a line pattern with a high sensitivity to actinic rays and a wide range of the focusing depth. The photoresist composition comprises, as a uniform mixture in the form of a solution, (a) an alkali-soluble novolac resin, (b) a naphthoquinone-1,2-diazido group-containing compound as a photosensitizing ingredient and (c) a specific phenolic triphenyl methane compound substituted by cyclohexyl groups on two of the phenyl groups, such as bis(3-cyclohexyl-4-hydroxy-6-methylphenyl)-3,4-dihydroxyphenyl methane or bis(3-cyclohexyl-6-hydroxy-4-methylphenyl)-3,4-dihydroxyphenyl methane, in a specified amount.
摘要翻译：提出了可用于抗蚀剂层的精细图案化工作的改进的正性光致抗蚀剂组合物，其能够提供具有高灵敏度的线图案的横截面轮廓的优异分辨率，耐热性和正交性的图案化抗蚀剂层光化射线和广泛的聚焦深度。光致抗蚀剂组合物包含作为溶液形式的均匀混合物，（a）碱溶性酚醛清漆树脂，（b）含萘醌-1,2-二叠氮基化合物作为光敏成分，（c）在两个苯基上的环己基取代的特异性酚类三苯基甲烷化合物，例如双（3-环己基-4-羟基-6-甲基苯基）-3,4-二羟基苯基甲烷或双（3-环己基-6-羟基 - 4-甲基苯基）-3,4-二羟基苯基甲烷。

4. 发明授权

US5601961A High-sensitivity positive-working photoresist composition 失效
标题翻译：高灵敏度正性光刻胶组合物
公开(公告)号：US5601961A
公开(公告)日：1997-02-11
申请号：US412889
申请日：1995-03-29
申请人： Kazuhiko Nakayama , Taku Nakao , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Kazuhiko Nakayama , Taku Nakao , Kousuke Doi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/022 , C08G8/08 , G03F7/023 , H01L21/027
CPC分类号： C08G8/08 , G03F7/0236
摘要： Disclosed is an improved positive-working photoresist composition comprising an alkali-soluble resin as a film-forming agent and a quinone diazide group-containing compound as a photosensitive agent. The most characteristic feature of the inventive composition consists in the unique formulation of the alkali-soluble resin which is a combination of two or three kinds of novolac resins selected from novolac resins (a), (b1) or (b2) and (c1) or (c2), each of which is characterized by the unique formulation of the phenolic compounds as a mixture to be subjected to a condensation reaction with an aldehyde compound to form the novolac resin. Namely, the phenolic mixture for the novolac (a) consists of m- and p-cresols, the phenolic mixture for the novolac (b1) consists of m-cresol and a xylenol, the phenolic mixture for the novolac (b2) consists of m- and p-cresols and a xylenol, the phenolic mixture for the novolac (c1) consists of m-cresol and a trimethyl phenol and the phenolic mixture for the novolac (c2) consists of m- and p-cresols and a trimethyl phenol each in a specified molar proportion of the constituent phenolic compounds.
摘要翻译：公开了一种改进的正性光致抗蚀剂组合物，其包含作为成膜剂的碱溶性树脂和含醌二叠氮基的化合物作为感光剂。本发明组合物最具特色的特征在于碱溶性树脂的独特配方，其是选自酚醛清漆树脂（a），（b1）或（b2）和（c1）中的两种或三种酚醛清漆树脂的组合，或（c2），其各自的特征在于酚类化合物作为与醛化合物进行缩合反应以形成酚醛清漆树脂的混合物的独特配方。即，酚醛清漆（a）的酚类混合物由间甲酚和对甲酚组成，酚醛清漆（b1）的酚类混合物由间甲酚和二甲苯酚组成，酚醛清漆（b2）的酚类混合物由 - 酚甲酚和二甲苯酚，酚醛清漆（c1）的酚类混合物由间甲酚和三甲酚组成，酚醛清漆（c2）的酚类混合物由间甲苯酚和对甲酚和三甲酚组成以规定摩尔比例的组成酚类化合物。

5. 发明授权

US5401605A Positive working photosensitive resin composition containing 1,2-naphthoquinone diazide esterification product of triphenylmethane compound 失效
标题翻译：含有三苯甲烷化合物的1,2-萘醌二叠氮化物酯化产物的正性感光性树脂组合物
公开(公告)号：US5401605A
公开(公告)日：1995-03-28
申请号：US282772
申请日：1994-07-29
申请人： Kousuke Doi , Hiroshi Hosoda , Kouichi Takahashi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Kousuke Doi , Hiroshi Hosoda , Kouichi Takahashi , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/022 , G03F7/023
CPC分类号： G03F7/022
摘要： Proposed is a positive-working photosensitive resin composition suitable as a photoresist in the photolithographic patterning work for the manufacture of, for example, semiconductor devices having excellent storage stability and capable of giving a patterned resist layer having excellent contrast of the images, orthogonality of the cross sectional profile of line patterns and heat resistance along with a satisfactorily high photosensitivity and large focusing latitude. The composition comprises, in admixture with an alkali-soluble novolac resin as a film-forming agent, a photosensitizing agent which is an esterification product of a specific tris(hydroxyphenyl) methane compound of which two of the hydroxyphenyl groups each have a cyclohexyl group bonded thereto at a specified position with at least one naphthoquinone-1,2-diazide sulfonyl group as the esterifying group.
摘要翻译：提出了在光刻图案工作中适合作为光致抗蚀剂的正性感光性树脂组合物，用于制造例如具有优异的储存稳定性的半导体器件，并且能够给出具有优异的图像对比度的图案化抗蚀剂层，线图形的横截面轮廓和耐热性以及令人满意的高光敏性和大的聚焦纬度。该组合物与作为成膜剂的碱溶性酚醛清漆树脂的混合物包含作为其中两个羟基苯基各自具有环己基基团的特定三（羟基苯基）甲烷化合物的酯化产物的光敏剂在指定位置与至少一个萘醌-1,2-二叠氮基磺酰基作为酯化基。

6. 发明授权

US5384228A Alkali-developable positive-working photosensitive resin composition 失效
标题翻译：碱显影正性感光树脂组合物
公开(公告)号：US5384228A
公开(公告)日：1995-01-24
申请号：US134287
申请日：1993-10-08
申请人： Kousuke Doi , Satoshi Niikura , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Kousuke Doi , Satoshi Niikura , Nobuo Tokutake , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： C07C309/76 , G03F7/022 , G03F7/023 , G03F7/30
CPC分类号： G03F7/022 , C07C309/76
摘要： A novel alkali-developable photosensitive resin composition, which is suitable for use as a photoresist composition for fine patterning in the manufacture of various electronic devices, is proposed. The photosensitive resin composition comprises, as the essential ingredients, (a) an alkali-soluble novolac resin as the film-forming ingredient and (b) a very specific compound which is a 1,2-quinone diazide sulfonic acid ester of a condensation product having a weight-average molecular weight of 400 to 2000 obtained by the condensation reaction between phenol and a hydroxybenzaldehyde in the presence of an acidic catalyst as the photosensitizing agent. By virtue of the formulation with this specific photosensitizer, the resist layer formed from the inventive composition has a greatly increased focusing latitude in addition to the excellent sensitivity, resolution and heat resistance.
摘要翻译：提出了一种新型的碱显影性感光性树脂组合物，其适合用作各种电子器件的制造中的精细图案化的光致抗蚀剂组合物。感光性树脂组合物含有（a）作为成膜成分的碱溶性酚醛清漆树脂和（b）作为缩合产物的1,2-醌二叠氮基磺酸酯的非常特殊的化合物，作为必要成分在酸性催化剂作为感光剂的存在下，通过苯酚与羟基苯甲醛之间的缩合反应得到的重均分子量为400〜2000。由于使用该特定光敏剂的配方，除了优异的灵敏度，分辨率和耐热性之外，由本发明组合物形成的抗蚀剂层具有大大提高的聚焦纬度。

7. 发明授权

US06939926B2 Phenol novolak resin, production process thereof, and positive photoresist composition using the same 有权
标题翻译：苯酚酚醛清漆树脂，其制备方法和使用其的正性光致抗蚀剂组合物
公开(公告)号：US06939926B2
公开(公告)日：2005-09-06
申请号：US10773294
申请日：2004-02-09
申请人： Ken Miyagi , Yasuhide Ohuchi , Atsuko Hirata , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Ken Miyagi , Yasuhide Ohuchi , Atsuko Hirata , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： C08G8/10 , C08G14/04 , G03F7/023 , C08G8/28
CPC分类号： G03F7/0236 , C08G14/04
摘要： A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 μm and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.
摘要翻译：苯酚酚醛清漆树脂在每个分子量分数基本上不变的树脂结构中具有邻 - 邻键（oo）/邻 - 对键（op）/对 - 对位键（pp）的峰强度比，并具有重均分子量分子量（Mw）为聚苯乙烯换算为3000〜20000，通过13 C-NMR分析检测出峰强度比。苯酚酚醛清漆树脂可以形成具有不大于0.35μm的精细抗蚀剂图案的良好形状的致密图案和隔离图案，并且具有令人满意的灵敏度，定义和焦深范围性质，并且具有均匀的树脂组合物每个分子量分数。还提供了一种制备苯酚酚醛清漆树脂的方法和使用该树脂的正性光致抗蚀剂组合物。

8. 发明授权

US06417317B1 Novolak resin precursor, novolak resin and positive photoresist composition containing the novolak resin 失效
标题翻译：酚醛清漆树脂前体，酚醛清漆树脂和含有酚醛清漆树脂的正性光致抗蚀剂组合物
公开(公告)号：US06417317B1
公开(公告)日：2002-07-09
申请号：US09459606
申请日：1999-12-13
申请人： Ken Miyagi , Kousuke Doi , Ryuusaku Takahashi , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Ken Miyagi , Kousuke Doi , Ryuusaku Takahashi , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： C08G1404
CPC分类号： G03F7/0236
摘要： A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho-ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.
摘要翻译：酚醛清漆树脂前体由键合的酚部分组成，相对于每个酚部分的羟基的邻位或对位中的氢原子之一被具有1至3个碳原子的烷基或烯基取代，并且其他两个氢原子通过亚甲基键键合。邻位键合的含量相对于总亚甲基的数量为30〜70％，前体的重均分子量为300〜10000。从该前体获得酚醛清漆树脂，正性光致抗蚀剂组合物包含该酚醛清漆树脂。本发明提供一种正光致抗蚀剂组合物，其包含较少的双核化合物，抑制浮渣形成，在定义和涂布性能方面优异，并提供具有令人满意的耐热性的抗蚀剂图案。

9. 发明授权

US06312863B1 Positive photoresist composition 失效
标题翻译：正光致抗蚀剂组合物
公开(公告)号：US06312863B1
公开(公告)日：2001-11-06
申请号：US09618723
申请日：2000-07-18
申请人： Shinichi Hidesaka , Atsushi Sawano , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Shinichi Hidesaka , Atsushi Sawano , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7023
CPC分类号： G03F7/022
摘要： A positive photoresist composition includes (A) an alkali-soluble resin, and (B) a photosensitizer including an ester of a 1,2-naphthoquinonediazidesulfonyl compound with a compound of the following formula (I). This positive photoresist composition has satisfactory sensitivity, definition, and depth of focus properties, can form both dense patterns and isolation patterns with good shapes in the formation of mixed resist patterns, and can minimize inverted taper shape formation of isolation resist patterns induced by shifts of focal depth to the minus side.
摘要翻译：正型光致抗蚀剂组合物包括（A）碱溶性树脂和（B）包含1,2-萘醌二叠氮化物化合物的酯与下式（I）的化合物的光敏剂。这种正性光致抗蚀剂组合物具有令人满意的灵敏度，定义和深度聚焦性能，可以在形成混合抗蚀剂图案时形成具有良好形状的致密图案和隔离图案，并且可以最小化反转锥形形成由隔离焦点深度为负侧。

10. 发明授权

US06296992B1 Positive photoresist composition and process for forming contact hole 有权
标题翻译：正光致抗蚀剂组合物和形成接触孔的方法
公开(公告)号：US06296992B1
公开(公告)日：2001-10-02
申请号：US09540539
申请日：2000-03-31
申请人： Masaki Kurihara , Satoshi Niikura , Miki Kobayashi , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Masaki Kurihara , Satoshi Niikura , Miki Kobayashi , Kousuke Doi , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F730
CPC分类号： G03F7/022 , G03F7/0226
摘要： A positive photoresist composition for forming a contact hole which comprises (A) an alkali-soluble resin; (B) a naphthoquinonediazide group-containing compound; and (C) a solvent, wherein the ingredient (B) comprises: at least one naphthoquinonediazidesulfonic ester of a polyphenol compound, where said polyphenol compound is composed of from 4 to 6 benzene rings each bonding via a methylene chain, each of the methylene chains is in a meta position to other methylene chains, and each of the benzene rings has a hydroxyl group is provided. According to tie present invention, a positive photoresist composition and a process for forming a contact hole can be provided each of which gives a contact hole pattern image in exact accordance with a mask pattern without dimple formation, in the contact hole forming technologies using the phaseshift method.
摘要翻译：一种用于形成接触孔的正性光致抗蚀剂组合物，其包含（A）碱溶性树脂; （B）含萘醌二叠氮化物基团的化合物; 和（C）溶剂，其中成分（B）包括：至少一种多酚化合物的萘醌二叠氮化物，其中所述多酚化合物由4-6个苯环组成，各自通过亚甲基键键合，每个亚甲基链位于其他亚甲基链的间位，并且提供每个苯环具有羟基。根据本发明，可以提供正性光致抗蚀剂组合物和用于形成接触孔的方法，其中每一种都在使用相移的接触孔形成技术中精确地根据没有凹坑形成的掩模图案给出接触孔图案图像方法。

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