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：US4731319A

公开(公告)日：1988-03-15

申请号：US886839

申请日：1986-07-18

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

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

IPC分类号： G03C1/72 ,  G03F7/022 ,  G03F7/023 ,  H01L21/027 ,  G03C1/54 ,  G03C1/60

CPC分类号： G03F7/0236

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 a cresol novolac resin and a naphthoquinone diazide sulfonic acid ester as the photosensitive component while the cresol novolac resin component is characteristically a combination of two different cresol novolac resins differentiated in respects of the weight-average molecular weight, one large and the other small, and the weight proportion of the m- and p-isomers of cresol, one rich in the m-isomer and the other rich in the p-isomer, used in the preparation of the novolac and the overall weight ratio of the m-cresol and p-cresol moieties in the thus combined cresol novolac resins also should be in a specified range.

摘要翻译： 适用于制造半导体器件的精细图案化的正性光致抗蚀剂组合物，例如， 提出了高保真的VLSI。 该组合物包含甲酚酚醛清漆树脂和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特征是两种不同甲酚酚醛清漆树脂的组合，其重均分子量分别为大，一 小的，并且用于制备酚醛清漆的甲酚和m-异构体的m-和p-异构体的重量比例，其中一个富含m-异构体和另一个富含p-异构体的重量比例， 这样组合的甲酚酚醛清漆树脂中的甲酚和对甲酚部分也应在特定的范围内。

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：US4906549A

公开(公告)日：1990-03-06

申请号：US182848

申请日：1988-04-18

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

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

IPC分类号： G03C1/72 ,  C08G8/12 ,  C08G8/24 ,  C08K5/43 ,  C08L61/08 ,  G03F7/023 ,  G03F7/025 ,  G03F7/22 ,  H01L21/027

CPC分类号： G03F7/0236 ,  C08G8/12 ,  C08G8/24 ,  C08K5/43

摘要： A positive-working photoresist composition suitable for fine patterning in the manufacturing of semiconductor devices such as VLSIs with high fidelity is proposed. The composition comprises: (A) 100 parts by weight of a phenolic novolac resin prepared by the condensation reaction of a specific ternary mixture of three kinds of phenolic compounds and formaldehyde; and (B) 20-60 parts by weight of a photosensitizer which is preferably an ester of naphthoquinone diazidesulfonic acid and a hydroxylated benzophenone compound. The phenolic mixture is composed of 10-45% by weight of m-cresol, 35-88% by weight of p-cresol and 2-30% by weight of a substituted phenol represented by the general formula R.C.sub.6 H.sub.4.OH, in which R is a monovalent aliphatic hydrocarbon group having 2-6 carbon atoms selected from alkyl and alkenyl groups.

摘要翻译： 提出了适用于制造半导体器件（例如具有高保真度的VLSI）的精细图案化的正性光致抗蚀剂组合物。 该组合物包括：（A）100重量份通过三种酚类化合物和甲醛的特定三元混合物的缩合反应制备的酚醛清漆树脂; 和（B）20-60重量份的优选萘醌二叠氮磺酸和羟基化二苯甲酮化合物的酯的光敏剂。 酚类混合物由10-45重量％的间甲酚，35-88重量％的对甲酚和2-30重量％的由通式R.C 6 H 4.OH表示的取代的苯酚组成，在 其中R为选自烷基和烯基的2-6个碳原子的一价脂族烃基。

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：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。

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：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。

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。

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。