公开(公告)号：US4174222A

公开(公告)日：1979-11-13

申请号：US881260

申请日：1978-02-27

申请人： Takashi Komine ,  Akira Yokota ,  Hisashi Nakane ,  Shingo Asaumi ,  Noboru Okazaki

发明人： Takashi Komine ,  Akira Yokota ,  Hisashi Nakane ,  Shingo Asaumi ,  Noboru Okazaki

IPC分类号： G03F7/022 ,  G03C1/54

CPC分类号： G03F7/022

摘要： A gallic acid alkyl ester or a gallic acid aryl ester is reacted in an inert solvent with 3 equivalents of naphthoquinone-(1,2)-diazido-(2)-sulfonyl chloride in the presence of an alkali to effect sulfonylation of 3 hydroxyl groups in the gallic acid moiety whereby a photodecomposable naphthoquinone-(1,2)-diazido-(2)-sulfonic acid ester is obtained. The new naphthoquinonediazido derivative thus obtained is mixed with an alkali-soluble phenol resin such as m-cresol novolac resin or phenol novolac resin to prepare a positive-type photoresist composition having high sensitivity and high resolving power as well as excellent dimensional accuracy and etching-resistance. In addition, this composition forms a good photosensitive film and can be a good ink receptor.

摘要翻译： 没食子酸烷基酯或没食子酸芳基酯在惰性溶剂中与3当量萘醌 - （1,2） - 叠氮基 - （2） - 磺酰氯在碱存在下反应，以实现3个羟基的磺酰化 在没食子酸部分中得到可光分解的萘醌 - （1,2） - 二叠氮基 - （2） - 磺酸酯。 将由此获得的新的萘醌二叠氮基衍生物与间甲酚酚醛清漆树脂或苯酚酚醛清漆树脂等碱溶性酚树脂混合，制备具有高灵敏度和高分辨能力的正型光致抗蚀剂组合物，以及优异的尺寸精度和蚀刻 - 抵抗性。 此外，该组合物形成良好的感光膜，并且可以是良好的油墨受体。

公开(公告)号：US4738915A

公开(公告)日：1988-04-19

申请号：US32952

申请日：1987-03-31

申请人： Takashi Komine ,  Shingo Asaumi ,  Akira Yokota ,  Hisashi Nakane

发明人： Takashi Komine ,  Shingo Asaumi ,  Akira Yokota ,  Hisashi Nakane

IPC分类号： G03C1/72 ,  G03F7/022 ,  H01L21/027 ,  G03C1/60

CPC分类号： G03F7/022

摘要： The invention provides an improvement over the conventional positive-working photoresist compositions comprising a novolac resin and an ester compound between 2,3,4-trihydroxybenzophenone and naphthoquinone-1,2-diazido-5-sulfonic acid in respect of scum formation in development and resistance of the patterned photoresist layer against heat and dry etching. The inventive composition comprises, in addition to the novolac resin and the ester compounds, 2,3,4-trihydroxybenzophenone in a specified amount relative to the ester compounds as a part of the photosensitive component which may be a reaction product obtained by the esterification reaction for the synthesis of the ester compounds containing unesterified 2,3,4-trihydroxybenzophenone.

摘要翻译： 本发明相对于在开发中的浮渣形成方面，相对于包含酚醛清漆树脂和2,3,4-三羟基二苯甲酮与萘醌-1,2-二叠氮基-5-磺酸之间的酯化合物的常规正性光致抗蚀剂组合物的改进， 图案化的光致抗蚀剂层对热和干蚀刻的电阻。 除酚醛清漆树脂和酯化合物之外，本发明组合物还包含相对于作为感光组分的一部分的酯化合物的特定量的2,3,4-三羟基二苯甲酮，其可以是通过酯化反应获得的反应产物 用于合成含有未酯化的2,3,4-三羟基二苯甲酮的酯化合物。

公开(公告)号：US4844832A

公开(公告)日：1989-07-04

申请号：US149971

申请日：1988-02-03

申请人： Masakazu Kobayashi ,  Shingo Asaumi ,  Akira Yokota ,  Hisashi Nakane

发明人： Masakazu Kobayashi ,  Shingo Asaumi ,  Akira Yokota ,  Hisashi Nakane

IPC分类号： G03C11/00 ,  C09D9/00 ,  G03F7/42 ,  H01L21/027 ,  H01L21/30

CPC分类号： G03F7/426 ,  C09D9/005

摘要： The remover solution for photoresist layers comprises: (a) from 30 to 70% by weight of an aromatic hydrocarbon compound or a combination of aromatic hydrocarbon compounds having a flash point of 70.degree. C. or higher containing at least a half amount of a naphthalenic compound selected from the group consisting of naphthalene, methyl naphthalenes and dimethyl naphthalenes; (b) from 5 to 40% by weight of a phenolic compound; and (c) from 10 to 50% by weight of an arylsulfonic acid. The remover solution is effective for a variety of photoresist compositions with less problems in respect to the workers' health and danger of fire and explosion than conventional remover solutions.

摘要翻译： 光致抗蚀剂层的去除剂溶液包括：（a）30至70重量％的芳族烃化合物或闪点为70℃或更高的含至少一半的萘的芳族烃化合物的组合 选自萘，甲基萘和二甲基萘的化合物; （b）5〜40重量％的酚类化合物; 和（c）10至50重量％的芳基磺酸。 去除剂溶液对于各种光刻胶组合物是有效的，与常规去除剂溶液相比，相对于工人的健康和火灾和爆炸危险的问题较少。

公开(公告)号：US4833067A

公开(公告)日：1989-05-23

申请号：US246930

申请日：1988-09-19

申请人： Hatsuyuki Tanaka ,  Hidekatsu Kohara ,  Yoshiyuki Sato ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

发明人： Hatsuyuki Tanaka ,  Hidekatsu Kohara ,  Yoshiyuki Sato ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

IPC分类号： G03C1/72 ,  G03C5/18 ,  G03F7/30 ,  G03F7/32 ,  H01L21/027 ,  H01L21/30

CPC分类号： G03F7/322 ,  G03C5/18

摘要： The aqueous developing solution of the invention for positive-working photoresist compositions contains, in addition to an organic basic compound free from metallic ions, such as tetramethyl ammonium hydroxide and choline, as the principal ingredient, from 50 to 5000 ppm of an acetylene alcohol. In comparison with conventional developing solutions, the inventive developing solution is advantageous in the uniformity of the patterned photoresist layer, higher sensitivity and smaller temperature dependency of development and less drawbacks due to foaming of the solution.

摘要翻译： 本发明的正性光致抗蚀剂组合物的水性显影液除了含有金属离子的有机碱性化合物外，还含有氢氧化四甲基铵和胆碱作为主要成分，为50-5000ppm的乙炔醇。 与传统的显影液相比，本发明的显影溶液在图案化光刻胶层的均匀性方面是有利的，更高的灵敏度和更小的显影温度依赖性以及由于溶液的发泡而引起的缺点。

公开(公告)号：US4385086A

公开(公告)日：1983-05-24

申请号：US100930

申请日：1979-12-06

申请人： Muneo Nakayama ,  Hisashi Nakane ,  Akira Yokota ,  Shingo Asaumi

发明人： Muneo Nakayama ,  Hisashi Nakane ,  Akira Yokota ,  Shingo Asaumi

IPC分类号： C09D4/00 ,  C09D5/00 ,  B05D3/02

CPC分类号： C09D5/00 ,  C03C17/004 ,  C03C17/23 ,  C09D4/00 ,  C23C18/1216 ,  C23C18/1241 ,  C23C18/1245 ,  C23C18/1283 ,  C03C2217/213 ,  C03C2217/78 ,  C03C2218/11

摘要： An efficient method is proposed for preventing leaching of contaminants from the surface of a solid, such as sodium ions from the surface of soda glass or nickel, chromium or iron from the surface of stainless steel in order to minimize detrimental contamination of highly pure substances in contact with the solid surface.The effect is basically obtained by providing a coating film of oxidized silicon on to the solid surface and the coating film is formed by applying a coating solution containing a hydroxysilane compound to the surface followed by baking of the coating layer at a temperature not lower than 150.degree. C., the coating solution being prepared by the equilibration reaction of an alkoxysilane with a carboxylic acid and an alcohol, of an acyloxysilane with an alcohol, or of an alkoxysilane with water in an alcohol where the molar ratios of the individual reactants are in the specified ranges.

摘要翻译： 提出了一种有效的方法，用于防止污染物从不锈钢表面的钠玻璃或镍，铬或铁表面的固体表面浸出，以最大限度地减少高纯度物质的有害污染 与固体表面接触。 通过在固体表面上设置氧化硅的涂膜，基本上得到效果，通过在表面涂布含有羟基硅烷化合物的涂布溶液，然后在不低于150℃的温度下进行涂布，形成涂膜 ℃，通过烷基硅烷与羧酸和醇与丙烯氧基硅烷与醇或烷氧基硅烷与醇在醇中的平衡反应制备的涂料溶液，其中各个反应物的摩尔比为 指定范围。

公开(公告)号：US5281508A

公开(公告)日：1994-01-25

申请号：US935131

申请日：1992-08-21

申请人： Hidekatsu Kohara ,  Hatsuyuki Tanaka ,  Masanori Miyabe ,  Yoshiaki Arai ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

发明人： Hidekatsu Kohara ,  Hatsuyuki Tanaka ,  Masanori Miyabe ,  Yoshiaki Arai ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

IPC分类号： C08G8/08 ,  C08K5/42 ,  G03F7/032 ,  G03F7/023

CPC分类号： G03F7/032 ,  C08G8/08 ,  C08K5/42

摘要： A positive-working photoresist composition suitable for fine patterning in the manufacture of semiconductor devices, e.g., VLSIs, with high fidelity is proposed. The composition comprises 100 parts by weight of a cresol novolac resin and 25-60 parts by weight of a naphthoquinone diazide sulfonic acid ester as the photosensitive component while the cresol novolac resin component is prepared from a mixture of cresol isomers composed of 35-43% of m-cresol and 65-57% of p-cresol with substantial absence of o-cresol or composed of 35-43% of m-cresol, 65-57% of p-cresol and 1% or less of o-cresol.

摘要翻译： 提出了适用于制造高保真度的半导体器件（例如VLSI）中的精细图案化的正性光致抗蚀剂组合物。 该组合物包含100重量份的甲酚酚醛清漆树脂和25-60重量份的萘醌二叠氮化物磺酸酯作为感光组分，而甲酚酚醛清漆树脂组分由由35-43％ 的间甲酚和65-57％的对甲酚，基本上没有邻甲酚或由35-43％的间甲酚，65-57％的对甲酚和1％或更少的邻甲酚组成。

公开(公告)号：US4784937A

公开(公告)日：1988-11-15

申请号：US892646

申请日：1986-08-04

申请人： Hatsuyuki Tanaka ,  Hidekatsu Kohara ,  Yoshiyuki Sato ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

发明人： Hatsuyuki Tanaka ,  Hidekatsu Kohara ,  Yoshiyuki Sato ,  Shingo Asaumi ,  Toshimasa Nakayama ,  Akira Yokota ,  Hisashi Nakane

IPC分类号： G03F7/32

CPC分类号： G03F7/322

摘要： The aqueous developing solution of the invention for positive-working photoresist compositions contains, in addition to an organic basic compound free from metal ions, such as tetramethyl ammonium hydroxide and choline, as the principal ingredient, from 50 to 5000 ppm of an anionic or non-ionic fluorine-containing surface active agent of specific types. In comparison with conventional developing solutions without such a surface active agent, the inventive developing solution is advantageous in the uniformity of the patterned photoresist layer and higher sensitivity and smaller temperature dependency of development.

摘要翻译： 本发明的正性光致抗蚀剂组合物的含水显影液除了含有金属离子的有机碱性化合物外，还含有氢氧化四甲基铵和胆碱作为主要成分，含有50-5000ppm阴离子或非离子表面活性剂 非离子型含氟表面活性剂。 与没有这种表面活性剂的常规显影溶液相比，本发明的显影溶液在图案化光致抗蚀剂层的均匀性方面是有利的，并且具有较高的灵敏度和较小的显影温度依赖性。

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。

公开(公告)号：US4824762A

公开(公告)日：1989-04-25

申请号：US67313

申请日：1987-06-26

申请人： Masakazu Kobayashi ,  Shingo Asaumi ,  Hatsuyuki Tanaka

发明人： Masakazu Kobayashi ,  Shingo Asaumi ,  Hatsuyuki Tanaka

IPC分类号： H01L21/30 ,  G03C11/00 ,  G03F7/00 ,  G03F7/26 ,  G03F7/42 ,  H01L21/027 ,  H01L21/461 ,  G03C11/12 ,  G03C5/00

CPC分类号： G03F7/425

摘要： The improvement of the invention consists in the use of a specific ether compound, e.g., diethyleneglycol monomethyl, monoethyl and monobutyl ethers, dipropyleneglycol monomethyl and monoethyl ethers, triethyleneglycol monomethyl and monoethyl ethers and tripropyleneglycol monomethyl ether, as a rinse solvent for a substrate from which the pattern photoresist layer has been removed with a remover solution in the photolithographic processing of semiconductor devices. The rinse solvent is free from the problems in the toxicity to human body and environment pollution relative to waste disposal as well as the danger of fire. The rinse solvent is versatile to be applicable to both of the negative- and positive-working photoresist compositions. Further advantages are obtained by adding an aliphatic amine compound to the rinse solvent.

摘要翻译： 本发明的改进在于使用特定的醚化合物，例如二甘醇单甲基，单乙基和单丁基醚，二丙二醇单甲基和单乙基醚，三乙二醇单甲基和单乙基醚和三丙二醇单甲醚作为底物的漂洗溶剂， 在半导体器件的光刻处理中，用去除剂溶液除去图案光致抗蚀剂层。 冲洗溶剂没有相对于废物处理对人体的毒性和环境污染的问题以及火灾的危险。 漂洗溶剂是通用的，适用于负性和正性光致抗蚀剂组合物。 通过向漂洗溶剂中加入脂族胺化合物可获得进一步的优点。

公开(公告)号：US4804612A

公开(公告)日：1989-02-14

申请号：US62954

申请日：1987-06-16

申请人： Shingo Asaumi ,  Hidekatsu Kohara ,  Hatsuyuki Tanaka ,  Toshimasa Nakayama

发明人： Shingo Asaumi ,  Hidekatsu Kohara ,  Hatsuyuki Tanaka ,  Toshimasa Nakayama

IPC分类号： G03C1/72 ,  C08G8/08 ,  G03C1/10 ,  G03F7/023 ,  G03F7/22 ,  H01L21/027 ,  G03C1/60 ,  G03C1/495

CPC分类号： C08G8/08 ,  G03F7/0236

摘要： Although the positive-working photoresist composition comprises a phenolic novolac resin as the film-forming component and a known photosensitizing compound as in conventional compositions, the novolac resin is prepared from a specific mixture of two classes of phenolic compounds including, one, phenol, cresols and/or resorcinol and, the other, one or more of the phenolic compounds having a nucleus-substituting group selected from allyloxy, allyloxymethyl, allyl dimethyl silyl, 2-(allyl dimethyl silyl) ethoxy, cinnamoyl, acryloyl and methacryloyl groups. By virtue of this unique combination to give the phenolic moiety in the novolac resin, the photoresist composition has markedly improved heat resistance as well as stability against plasma in dry etching so that the composition can give a patterned photoresist layer with extreme fineness having high fidelity to the mask pattern.

摘要翻译： 尽管正性光致抗蚀剂组合物包含作为成膜组分的酚醛酚醛树脂和常规组合物中已知的光敏化合物，但酚醛清漆树脂由两类酚类化合物的特定混合物制备，包括一种酚类，甲酚 和/或间苯二酚，另一种，一种或多种具有选自烯丙氧基，烯丙氧基甲基，烯丙基二甲基甲硅烷基，2-（烯丙基二甲基甲硅烷基）乙氧基，肉桂酰基，丙烯酰基和甲基丙烯酰基的取代基的酚类化合物。 由于这种独特的组合使得酚醛部分在酚醛清漆树脂中，光致抗蚀剂组合物在干蚀刻中具有显着改善的耐热性以及抗等离子体的稳定性，使得组合物可以给出具有高保真度的极细度的图案化光致抗蚀剂层 掩模图案。