公开(公告)号：US5429905A

公开(公告)日：1995-07-04

申请号：US227011

申请日：1994-04-13

申请人： Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

发明人： Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

IPC分类号： G03F7/022 ,  H01L21/027 ,  G03F7/023

CPC分类号： G03F7/022

摘要： The present invention relates to a positive-working photoresist composition comprising at least one of the 1,2-naphthoquinonediazido-5- sulfonic acid ester of a polyhydroxy compound represented by formula (1) and the 1,2-naphthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound represented by formula (1): ##STR1## wherein R represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, or an alkenyl group; and R.sub.1 to R.sub.15, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a substituted or unsubstituted cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.15 is a substituted or unsubstituted cycloalkyl group.

摘要翻译： 本发明涉及一种正性光致抗蚀剂组合物，其包含由式（1）表示的多羟基化合物的1,2-萘醌二叠氮基-5-磺酸酯和1,2-萘醌二叠氮基-4-磺酸中的至少一种 由式（1）表示的多羟基化合物的酯：其中R表示氢原子，羟基，卤素原子，硝基，具有1至6个碳原子的烷基，芳基 基团或烯基; R 1〜R 15可以相同或不同，表示氢原子，羟基，卤素原子，碳原子数1〜6的烷基，烷氧基或取代或未取代的环烷基， 条件是R 1至R 15中的至少一个是取代或未取代的环烷基。

公开(公告)号：US5494773A

公开(公告)日：1996-02-27

申请号：US399046

申请日：1995-03-06

申请人： Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

发明人： Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

IPC分类号： G03F7/022 ,  G03F7/023 ,  H01L21/027

CPC分类号： G03F7/0236

摘要： A positive photoresist composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound is described, wherein the alkali-soluble novolak resin contains a novolak resin to be obtained by condensing a mixture of (a) at least one phenol represented by the following formula (1) and at least one compound represented by the following formula (2) and (b) at least one aldehyde: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group or an arylcarbonyl group; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryl group or an aralkyl group; and n represents an integer of from 4 to 7.

摘要翻译： 描述了包含碱溶性酚醛清漆树脂和1,2-醌二叠氮化合物的正型光致抗蚀剂组合物，其中碱溶性酚醛清漆树脂含有酚醛清漆树脂，其通过将（a）至少一种由 （1）和至少一种由下式（2）和（b）表示的化合物至少一种醛：其中R 1，R 2和R 3相同或不同， 各自表示氢原子，羟基，卤素原子，烷基，烷氧基，烯基，芳基，芳烷基，烷氧基羰基或芳基羰基; R4，R5，R6和R7相同或不同，各自表示氢原子，羟基，卤素原子，烷基，环烷基，烷氧基，烯基，芳基或芳烷基 ; n表示4〜7的整数。

公开(公告)号：US5324618A

公开(公告)日：1994-06-28

申请号：US985259

申请日：1992-12-03

申请人： Yasumasa Kawabe ,  Shiro Tan ,  Tadayoshi Kokubo

发明人： Yasumasa Kawabe ,  Shiro Tan ,  Tadayoshi Kokubo

IPC分类号： G03F7/022 ,  H01L21/027 ,  G03F7/023 ,  G03C1/61

CPC分类号： G03F7/0226

摘要： Disclosed is a positive type photoresist composition comprising an alkali-soluble resin, a quinone diazide compound and a compound represented by the following general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and in which four groups for each group may be different from each other at the same time, each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, a nitro group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, an aryloxy group or an aralkoxy group; a, b, d and e each represents 0 or an integer 1 to 3; and c represents 0 or 1, with the proviso that a, b, c, d and e satisfy the relationship (a+b+c+d+e.gtoreq.2), at least one of a and d is 1 or more and at least one of b and e is 1 or more.

摘要翻译： 公开了一种正型光致抗蚀剂组合物，其包含碱溶性树脂，醌二叠氮化合物和由以下通式（I）表示的化合物：其中R 1，R 2，R 3和R 4可以相同 或者不同，并且每个基团的四个基团可以同时彼此不同，各自表示氢原子，羟基，卤素原子，烷基，烷氧基，硝基，烯基 芳基，芳烷基，烷氧基羰基，芳基羰基，酰氧基，酰基，芳氧基或芳烷氧基; a，b，d和e各自表示0或整数1〜3; 并且c表示0或1，条件是a，b，c，d和e满足关系式（a + b + c + d + e> / = 2），a和d中的至少一个为1或更大 b和e中的至少一个为1以上。

公开(公告)号：US5318875A

公开(公告)日：1994-06-07

申请号：US15921

申请日：1993-02-10

申请人： Yasumasa Kawabe ,  Toshiaki Aoai ,  Tadayoshi Kokubo ,  Shiro Tan

发明人： Yasumasa Kawabe ,  Toshiaki Aoai ,  Tadayoshi Kokubo ,  Shiro Tan

IPC分类号： C07C45/46 ,  G03F7/022 ,  G03F7/023 ,  G03C1/61

CPC分类号： G03F7/0226 ,  C07C45/46 ,  G03F7/022

摘要： A positive photoresist composition includes an alkali-soluble resin, a quinonediazide compound and a compound selected from the group consisting of compounds represented by formulae (I), (II) and (III): ##STR1## wherein R.sub.1 to R.sub.27, which may be the same or different, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group, nitro group, alkenyl group, aryl group, aralkyl group, alkoxycarbonyl group, arylcarbonyl group, acyloxy group, acyl group, aryloxy group or aralkoxy group; ##STR2## wherein R.sub.31 represents an organic group, single bond, ##STR3## R.sub.32 represents a hydrogen atom, monovalent organic group or ##STR4## R.sub.33 to R.sub.37, which may be the same or different, and in which not all four groups for each of R.sub.33 to R.sub.37 may be the same at the same time, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group or alkenyl group, with the proviso that at least one of R.sub.33 to R.sub.35 is a hydroxyl group; X represents a divalent organic group; and m represents an integer 0 or 1; ##STR5## wherein R.sub.41 to R.sub.44, which may be the same or different and in which not all four groups for each of R.sub.41 to R.sub.44 may be the same at the same time, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group or alkenyl group; R.sub.45 and R.sub.46 each represents a hydrogen atom, alkyl group or ##STR6## a and c each represents an integer 0 or 1; and b represents an integer from 1 to 4.

摘要翻译： 正型光致抗蚀剂组合物包括碱溶性树脂，醌二叠氮化合物和选自由式（I），（II）和（III）表示的化合物的化合物：其中R 1至R 27， 可以相同或不同，分别表示氢原子，羟基，卤素原子，烷基，烷氧基，硝基，烯基，芳基，芳烷基，烷氧基羰基，芳基羰基，酰氧基，酰基， 芳氧基或芳烷氧基; （II）其中R31表示有机基团，单键，R32表示氢原子，一价有机基团或R33至R37，其可以相同或不同，并且其中并不全部为四 R 33〜R 37各自可以相同，各自表示氢原子，羟基，卤素原子，烷基，烷氧基或烯基，条件是R 33〜R 35中的至少一个为 羟基; X表示二价有机基团; m表示0或1的整数; （III）其中R41〜R44可以相同或不同，并且其中R41至R44中的每一个不是全部四个基团可以同时相同，各自表示氢原子，羟基，卤素 原子，烷基，烷氧基或烯基; R 45和R 46各自表示氢原子，烷基或者a和c各自表示0或1的整数; b表示1〜4的整数。

公开(公告)号：US5576139A

公开(公告)日：1996-11-19

申请号：US783346

申请日：1991-10-28

申请人： Kazuya Uenishi ,  Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

发明人： Kazuya Uenishi ,  Shiro Tan ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

IPC分类号： C08G8/08 ,  C08L61/04 ,  C08L61/06 ,  G03F7/022 ,  G03F7/023 ,  H01L21/027

CPC分类号： C08G8/08 ,  G03F7/022 ,  G03F7/0236

摘要： A novel positive type photoresist composition is provided, comprising an alkali-soluble novolak resin obtained by the condensation of substituted or unsubstituted phenols and aldehydes in the presence of a silica-magnesia solid catalyst and a light-sensitive material containing 1,2-naphthoquinone-diazido-5-(and/or -4-) sulfonate as main component.

摘要翻译： 提供了一种新型的正型光致抗蚀剂组合物，其包含通过在二氧化硅 - 氧化镁固体催化剂和含有1,2-萘醌的固体催化剂存在下缩合取代或未取代的酚和醛而获得的碱溶性酚醛清漆树脂， 重氮基-5-（和/或-4-）磺酸盐为主要成分。

公开(公告)号：US5674657A

公开(公告)日：1997-10-07

申请号：US743592

申请日：1996-11-04

申请人： Shiro Tan ,  Yasumasa Kawabe ,  Kenji Honda

发明人： Shiro Tan ,  Yasumasa Kawabe ,  Kenji Honda

IPC分类号： C08L61/06 ,  G03F7/022 ,  G03F7/023 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0236 ,  G03F7/022

摘要： The invention is directed to an alkali-soluble novolak binder resin composition made by addition condensation reaction of a phenolic mixture with at least one aldehyde source, the feedstock of said phenolic mixture for the reaction comprising about 33 to about 83 mole percent of meta-cresol; about 1 to about 4 mole percent of para-cresol; about 10 to about 60 mole percent of a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol and mixtures thereof; and about 5 to about 55 mole percent of a methoxy phenol monomer, the amount of aldehyde source being from about 40 to about 200 percent of the stoichiometric amount needed to react with all of the phenolic moieties in said phenolic mixture, and the alkali-soluble novolak binder resin having a weight average molecular weight (M.sub.w) of about 3,000 to about 20,000 with a molecular weight polydispersity (M.sub.w /M.sub.n) of 1.5-4.0. The invention is also directed to a positive working photoresist made from the composition.

摘要翻译： 本发明涉及通过酚类混合物与至少一种醛源的加成缩合反应制备的碱溶性酚醛清漆粘合剂树脂组合物，所述用于反应的酚类混合物的原料包含约33-约83摩尔％的间甲酚 ; 约1至约4摩尔％的对 - 甲酚; 约10至约60摩尔％的选自2,3-二甲苯酚，3,4-二甲苯酚，3,5-二甲苯酚及其混合物的酚单体; 和约5至约55摩尔％的甲氧基酚单体，醛源的量为所述酚类混合物中所有酚部分反应所需化学计量的约40至约200％，碱溶性 酚醛清漆粘合剂树脂，重均分子量（Mw）约为3,000至约20,000，分子量多分散性（Mw / Mn）为1.5-4.0。 本发明还涉及由该组合物制成的正性工作光致抗蚀剂。

公开(公告)号：US5380618A

公开(公告)日：1995-01-10

申请号：US230020

申请日：1994-04-19

申请人： Tadayoshi Kokubo ,  Kazuya Uenishi ,  Shiro Tan ,  Wataru Ishii

发明人： Tadayoshi Kokubo ,  Kazuya Uenishi ,  Shiro Tan ,  Wataru Ishii

IPC分类号： C08K5/42 ,  C09D161/06 ,  G03F7/022 ,  G03F7/023 ,  H01L21/027 ,  H01L21/30 ,  G03F7/30

CPC分类号： G03F7/0236 ,  C08K5/42 ,  C09D161/06 ,  G03F7/022

摘要： A micropattern-forming, light sensitive resin composition is disclosed. The composition comprises (a) a novolak resin comprising a condensate between formaldehyde and a mixture of m-cresol and p-cresol with a m-cresol to p-cresol charging weight ratio of from 45/55 to 60/40, wherein the novolak resin has the following characteristics: (i) a dissolving rate of 20 to 800 .ANG./sec in an aqueous solution of tetramethylammonium hydroxide (TMAH) and an alkali activity of 0.131N, (ii) a weight average molecular weight of 1000 to 6000 calculated as polystyrene equivalent, and (iii) a non-exposed dissolving rate of equal to or more than 100 .ANG./sec in an aqueous solution of TMAH with an alkali activity of 0.262N; (b) a light-sensitive substance of 1,2-naphthoquinonediazide-4-sulfonyl ester, and (c) a solvent capable of dissolving the novolak resin and the light-sensitive substance; wherein the novolak resin, the light-sensitive substance, and the solvent are present in such amounts that a 1.0 micron thick resist formed of the material has an optical density at 382 nm of 0.1 to 0.4 .mu.m.sup.-1. Also described is a micropattern-forming process having the steps of: (1) spin coating a substrate with the light-sensitive resin composition; (2) drying the light-sensitive composition; (3) exposing the dried light-sensitive composition using deep UV having a wavelength not longer than about 320 nm; and (4) developing the exposed light-sensitive composition.

摘要翻译： 公开了一种形成微图案的光敏树脂组合物。 所述组合物包含（a）包含甲醛与间甲酚与对甲酚的混合物之间的缩合物的酚醛清漆树脂，间甲酚与对甲酚的重量比为45/55至60/40，其中酚醛清漆 树脂具有以下特征：（i）在四甲基氢氧化铵（TMAH）的水溶液中的溶解速率为20-800μG/ s，碱性活性为0.131N，（ii）重均分子量为1000〜6000的计算值 作为聚苯乙烯当量，和（iii）在碱性活性为0.262N的TMAH的水溶液中等于或大于100安培/秒的未暴露的溶解速率; （b）1,2-萘醌二叠氮化物-4-磺酰基酯的光敏物质，和（c）可溶解酚醛清漆树脂和光敏物质的溶剂; 其中酚醛清漆树脂，感光物质和溶剂的存在量使得由该材料形成的1.0微米厚的抗蚀剂的光密度在382nm为0.1至0.4μm-1。 还描述了一种微图案形成方法，其具有以下步骤：（1）用感光树脂组合物旋涂基材; （2）干燥感光组合物; （3）使用波长不大于约320nm的深UV曝光干燥的感光组合物; 和（4）显影曝光的感光组合物。

公开(公告)号：US5340686A

公开(公告)日：1994-08-23

申请号：US173924

申请日：1993-12-28

申请人： Shinji Sakaguchi ,  Shiro Tan ,  Tadayoshi Kokubo

发明人： Shinji Sakaguchi ,  Shiro Tan ,  Tadayoshi Kokubo

IPC分类号： G03F7/004 ,  G03F7/022 ,  G03F7/023 ,  H01L21/027 ,  H01L21/30 ,  G03F7/30

CPC分类号： G03F7/0226 ,  G03F7/0236

摘要： A positive-type photoresist composition is described as including:(1) an alkali-soluble phenol novolak having a degree of dispersion of from 1.5 to 4.0;(2) a 1,2-quinone diazide compound; and(3) from 2 to 30% by weight, based on the above-mentioned novolak, of a low molecular weight compound having a total of from 12 to 50 carbon atoms per molecule and 2 to 8 phenolic hydroxyl groups per molecule. The degree of dispersion is determined from a weight-average molecular weight of the novolak and a number-average molecular weight of the novolak, both the weight-average and number-average molecular weights being obtained by gel penetration chromatography (GPC) defined by using standard polystyrene as a reference, such that the degree of dispersion is a ratio of the weight-average molecular weight to the number average molecular weight.The positive-type photoresist composition of the present invention is excellent in development latitude and has a high sensitivity and a high resolving power. Thus, it is suitable for use in, for example, the production of semiconductors such as integrated circuits, the production of circuit substrates for thermal heads, and photofabrication processes.

摘要翻译： 正型光致抗蚀剂组合物包括：（1）分散度为1.5〜4.0的碱溶性酚醛清漆; （2）1,2-醌二叠氮化合物; 和（3）基于上述酚醛清漆的2至30重量％的每分子具有总共12至50个碳原子的低分子量化合物和每分子2至8个酚羟基。 分散度由酚醛清漆的重均分子量和酚醛清漆的数均分子量确定，通过使用通过凝胶渗透色谱法（GPC）得到的重均分子量和数均分子量均为 标准聚苯乙烯作为参考，使得分散度是重均分子量与数均分子量的比率。 本发明的正型光致抗蚀剂组合物的显影宽度优良，灵敏度高，分辨率高。 因此，适用于例如集成电路等半导体的制造，热敏头的电路基板的制造以及光制造工序。

公开(公告)号：US5709977A

公开(公告)日：1998-01-20

申请号：US677143

申请日：1996-07-09

申请人： Shiro Tan ,  Yasumasa Kawabe

发明人： Shiro Tan ,  Yasumasa Kawabe

IPC分类号： G03F7/023

CPC分类号： G03F7/0236

摘要： Provided is a positive working photoresist composition which comprises a 1,2-quinonediazide compound and an alkali-soluble resin obtained by condensing a specified phenol compound, formaldehyde and a specified aromatic aldehyde having at least one alkoxy substituent and at least one hydroxy substituent.

摘要翻译： 提供一种正性光致抗蚀剂组合物，其包含1,2-醌二叠氮化合物和通过使特定的酚化合物，甲醛和具有至少一个烷氧基取代基的特定芳香醛和至少一个羟基取代基缩合而获得的碱溶性树脂。

公开(公告)号：US5620828A

公开(公告)日：1997-04-15

申请号：US579410

申请日：1995-12-27

申请人： Shiro Tan ,  Yasumasa Kawabe

发明人： Shiro Tan ,  Yasumasa Kawabe

IPC分类号： G03F7/004 ,  G03F7/023 ,  H01L21/027

CPC分类号： G03F7/0236

摘要： A positive photoresist composition is disclosed, which comprises prescribed amounts of an alkali-soluble novolak resin which is obtained from prescribed amounts of m- and p-cresols and at least one xylenol selected from 2,3-, 3,4- and 3,5-xylenols and an aldehyde, a 1,2-quinonediazide compound which is an esterified product of a polyhydroxy compound having from 3 to 7 phenolic hydroxyl groups in the molecule with 1,2-naphthoquinonediazido-5(and/or 4)-sulfonyl chloride(s) and an alkali dissolution accelerator which is a polyhydroxy compound having a molecular weight of 1,000 or less and from 2 to 7 phenolic hydroxyl groups in the molecule.

摘要翻译： 公开了一种正型光致抗蚀剂组合物，其包含规定量的由规定量的间甲酚和对甲酚获得的碱溶性酚醛清漆树脂和至少一种选自2,3-，3,4-和3的二甲苯酚， 5-二甲苯酚和醛，1,2-醌二叠氮化合物，其是分子中具有3-7个酚羟基的多羟基化合物与1,2-萘醌二叠氮基-5（和/或4） - 磺酰基的酯化产物 氯化物和碱溶解促进剂，其为分子中分子量为1,000以下且为2〜7个酚羟基的多羟基化合物。