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1. 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。

2. 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。

3. 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。

4. 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。

5. 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。

6. 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。

7. 发明授权

US5332647A Positive-working quinone diazide composition containing N,N',N"-substituted isocyanurate compound and associated article 失效
标题翻译：含N，N'，N“ - 取代的异氰脲酸酯化合物和相关制品的正性醌醌二叠氮化合物组合物
公开(公告)号：US5332647A
公开(公告)日：1994-07-26
申请号：US111179
申请日：1993-08-24
申请人： Hayato Ohno , Nobuo Tokutake , Satoshi Niikura , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Hayato Ohno , Nobuo Tokutake , Satoshi Niikura , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/022 , G03F7/09 , G03C1/61 , G03F7/023
CPC分类号： G03F7/0226
摘要： A positive-working photosensitive resin composition useful as a photoresist material in the fine patterning work for the manufacture of semiconductor devices is proposed. The composition is excellent in the storage stability and capable of giving a patterned resist layer having good film thickness retention, cross sectional profile of line patterns, resolution and heat resistance. The composition comprises, in addition to a conventional alkali-soluble novolac resin as a film-forming agent and a quinone diazide group containing compound as a photosensitizing agent, a specific isocyanurate compound substituted at each nitrogen atom with a hydroxy- and ter-butyl-substituted benzyl group.
摘要翻译：提出了用于制造半导体器件的精细图案化工作中用作光致抗蚀剂材料的正性感光性树脂组合物。该组合物的保存稳定性优异，能够得到具有良好的膜厚保持性，线图案的横截面轮廓，分辨率和耐热性的图案化抗蚀剂层。该组合物除了常规的作为成膜剂的碱溶性酚醛清漆树脂和含有醌二叠氮基的化合物作为感光剂之外，还包括在每个氮原子处被羟基和叔丁基取代的异氰脲酸酯化合物，取代的苄基。

8. 发明授权

US4985333A Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin 失效
标题翻译：具有三个不同的1,2-萘醌二叠氮磺酸酯的正性感光组合物，包括姜黄素的酯
公开(公告)号：US4985333A
公开(公告)日：1991-01-15
申请号：US385820
申请日：1989-07-27
申请人： Nobuo Tokutake , Koichi Takahashi , Yoshiyuki Satoh , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Nobuo Tokutake , Koichi Takahashi , Yoshiyuki Satoh , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： C08L61/08 , G03F7/022
CPC分类号： G03F7/022
摘要： The positive-working photosensitive composition useful as a material of photoresist comprises, in addition to a film-forming resin, such as a cresol novolak resin, and a photosensitive compound, such as an ester of a polyhydroxy benzophenone and 1,2-naphthoquinonediazido-5-sulfonic acid, an esterification product of curcumin with 1,2-naphthoquinone diazide sulfonic acid in a limited amount. The photosensitive composition is outstandingly insusceptible to the adverse influence of halation even when the photoresist layer is formed on a highly reflective aluminum-deposited surface of a substrate without decreasing the photosensitivity of the composition to actinic rays in the photolithographic process for the manufacture of semiconductor devices.
摘要翻译：可用作光致抗蚀剂材料的正性感光性组合物除了成膜树脂以外，例如甲酚酚醛清漆树脂和光敏化合物，例如多羟基二苯甲酮的酯和1,2-萘醌二叠氮基 - 5-磺酸，姜黄素与1,2-萘醌二叠氮磺酸的酯化产物有限。即使当光致抗蚀剂层形成在基板的高反射性铝沉积表面上时，光敏组合物对于不利影响也是显着的，而不会在用于制造半导体器件的光刻工艺中降低组合物对光化射线的光敏性。

9. 发明授权

US5498514A Lithographic double-coated patterning plate with undercoat levelling layer 失效
标题翻译：平版印刷双层涂层图案板，底层平整层
公开(公告)号：US5498514A
公开(公告)日：1996-03-12
申请号：US287895
申请日：1994-08-09
申请人： Taku Nakao , Hiroyuki Yamazaki , Nobuo Tokutake , Masato Saito , Hidekatsu Kohara , Toshimasa Nakayama
发明人： Taku Nakao , Hiroyuki Yamazaki , Nobuo Tokutake , Masato Saito , Hidekatsu Kohara , Toshimasa Nakayama
IPC分类号： G03F7/09 , G03C1/815
CPC分类号： G03F7/094
摘要： An improvement is proposed in a double-coated patterning plate, which consists of a substrate, an undercoat levelling layer and a photoresist layer thereon, as well as in the patterning method therewith. Different from conventional double-coated patterning plate in which the undercoat levelling layer is formed from poly(methyl methacrylate) resin, the layer in the invention is formed from a copolymeric resin of methyl methacrylate and glycidyl methacrylate in a specified copolymerization ratio and the resin is admixed with 2,2',4,4'-tetrahydroxybenzophenone. By virtue of the use of this unique resin composition for the undercoat levelling layer, the troubles due to intermixing between the undercoat levelling layer and the photoresist layer thereon can be avoided to impart the patterned resist layer with excellent properties.
摘要翻译：在其中由基底，底涂层流平层和光致抗蚀剂层组成的双面图案化板以及其图案化方法中提出了一种改进。与由聚（甲基丙烯酸甲酯）树脂形成底层平整层的常规双面图案化板不同，本发明的层由特定共聚比例的甲基丙烯酸甲酯和甲基丙烯酸缩水甘油酯的共聚树脂形成，树脂为与2,2'，4,4'-四羟基二苯甲酮混合。由于使用这种独特的树脂组合物作为底层调平层，所以可以避免由于底层平整层和其上的光致抗蚀剂层之间的混合所引起的问题，以赋予图案化抗蚀剂层优异的性能。

10. 发明授权

US4882260A Positive-working photosensitive quinone diazide composition with alkali insoluble dye and alkali soluble dye 失效
标题翻译：正色光敏醌二叠氮化合物与碱不溶性染料和碱溶性染料
公开(公告)号：US4882260A
公开(公告)日：1989-11-21
申请号：US059556
申请日：1987-06-05
申请人： Hidekatsu Kohara , Nobuo Tokutake , Masanori Miyabe , Toshimasa Nakayama , Shingo Asaumi , Hatsuyuki Tanaka , Yoshiaki Arai
发明人： Hidekatsu Kohara , Nobuo Tokutake , Masanori Miyabe , Toshimasa Nakayama , Shingo Asaumi , Hatsuyuki Tanaka , Yoshiaki Arai
IPC分类号： G03C1/00 , C09D161/08 , G03C1/72 , G03F7/004 , G03F7/022 , G03F7/025 , G03F7/04 , G03F7/09 , H01L21/027 , H01L21/30
CPC分类号： G03F7/091
摘要： The photosensitive composition, which is suitable as a photoresist material in fine patterning works for the manufacture of semiconductor devices, contains, as a photoextinctive agent, a combination of an alkali-insoluble dye and an alkali-soluble dye each having absorptivity of light in the wavelength region from 230 to 500 nm in a specified amount and in a specified ratio between them. By virtue of the formulation of combined dyes, the undesirable phenomenon of halation by the underlying aluminum coating layer on the substrate surface is greatly decreased so that patterned resist layer obtained with the composition is a high-fidelity reproduction of the original pattern even in a submicron range of fineness with good rectangularity of the cross sectional form of the patterned lines.
摘要翻译：在制造半导体器件的精细图案化中适合作为光致抗蚀剂材料的光敏组合物包含作为光敏剂的碱不溶性染料和碱溶性染料的组合，其中每种具有光吸收性的染料波长范围为230〜500nm，以规定的量和它们之间的规定比例。由于组合染料的配制，基板表面上的下面的铝涂层的不期望的卤化现象大大降低，使得用该组合物获得的图案化抗蚀剂层即使在亚微米中也是原始图案的高保真再现图案线的横截面形状的良好矩形度的细度范围。

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