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1. 发明授权

US5290656A Resist composition, novel phenol compound and quinone diazide sulfonic acid ester of novel phenol compound 失效
标题翻译：抗酚组合物，新型苯酚化合物和醌二叠氮磺酸酯新型酚类化合物
公开(公告)号：US5290656A
公开(公告)日：1994-03-01
申请号：US5429
申请日：1993-01-19
申请人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Yukio Hanamoto , Fumio Oi , Jun Tomioka
发明人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Yukio Hanamoto , Fumio Oi , Jun Tomioka
IPC分类号： G03F7/022 , G03C1/52 , C07C309/76
CPC分类号： G03F7/022
摘要： A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I): ##STR1## wherein Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are the same or different and each a hydrogen atom, an alkyl group, a halogen atom or a hydroxyl group, provided that at least one of Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 is a hydroxyl group; Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 are the same or different and each a hydrogen atom, an alkyl, an aryl group, a halogen atom or a hydroxyl group, provided that at least one of Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 is a hydroxyl group; X is ##STR2## in which R.sub.1 and R.sub.2 are the same or different and each a hydrogen atom, an alkyl group, an alkenyl group, a cyclo-alkyl group, an alkoxy group or an aryl group, provided that when at least one of R.sub.1 and R.sub.2 is a hydrogen atom, an alkyl or aryl group is present at the ortho position to a hydroxyl group which is present at the ortho position to X provides a positive resist composition which has a high .gamma.-value.
摘要翻译：通式（I）的酚化合物的醌二叠氮磺酸酯：其中Y 1，Y 2，Y 3和Y 4相同或不同，各自为氢原子，烷基，卤素原子或羟基，条件是Y 1，Y 2，Y 3和Y 4中的至少一个为羟基; Z 1，Z 2，Z 3，Z 4，Z 5和Z 6相同或不同，各自为氢原子，烷基，芳基，卤素原子或羟基，条件是Z1，Z2，Z3，Z4中的至少一个 Z5和Z6是羟基; X为，其中R 1和R 2相同或不同，并且各自为氢原子，烷基，烯基，环烷基，烷氧基或芳基，条件是当至少一个 R1和R2是氢原子，烷基或芳基存在于与X的邻位存在的羟基的邻位，提供具有高γ值的正性抗蚀剂组合物。

2. 发明授权

US5059507A Positive resist composition containing quinone diazide sulfonic acid ester of a phenol compound and an alkali soluble resin 失效
标题翻译：酚醛化合物和碱性可溶性树脂的喹啉二异氰酸酯的积极抗性组合物
公开(公告)号：US5059507A
公开(公告)日：1991-10-22
申请号：US364123
申请日：1989-06-12
申请人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Yukio Hanamoto , Fumio Oi
发明人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Yukio Hanamoto , Fumio Oi
IPC分类号： G03F7/022 , H01L21/027
CPC分类号： G03F7/022
摘要： A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I): ##STR1## wherein Y.sub.1 and Y.sub.2 are each a hydrogen atom, an alkyl group or a hydroxyl group, provided that at least one of Y.sub.1 and Y.sub.2 is a hydroxyl group; Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are the same or different and each a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, an aryl group or halogen atom, provided that at least two of Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are hydroxyl groups; R.sub.1, R.sub.2 and R.sub.3 are the same or different and each a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group provides a positive resist composition having a high .gamma.-value.

3. 发明授权

US5124228A Positive photoresist composition containing alkali-soluble resin and o-quinone diazide sulfonic acid ester 失效
标题翻译：含有碱性可溶性树脂和O-喹啉二酸硫酸酯的阳性光电组合物
公开(公告)号：US5124228A
公开(公告)日：1992-06-23
申请号：US381298
申请日：1989-07-18
申请人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Fumio Oi
发明人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Fumio Oi
IPC分类号： G03F7/022
CPC分类号： G03F7/0226
摘要： A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I) or (II): ##STR1## wherein a, c and d are the same or different and a number of 0 to 3, provided that when a is 0 or 3, b is a number of 0 to 3 or when a is 1 or 2, b is 0, 1 or 2, and a+b and c+d are not less than 2; R and R' are the same or different and an alkyl group or an aryl group provides a positive resist composition having a high .gamma.-value.

4. 发明授权

US5378586A Resist composition comprising a quinone diazide sulfonic diester and a quinone diazide sulfonic complete ester 失效
标题翻译：抗蚀剂组合物，其包含醌二叠氮磺酸二酯和醌二叠氮磺酸酯
公开(公告)号：US5378586A
公开(公告)日：1995-01-03
申请号：US152891
申请日：1993-11-16
申请人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Fumio Oi
发明人： Yasunori Uetani , Makoto Hanabata , Hirotoshi Nakanishi , Koji Kuwana , Fumio Oi
IPC分类号： G03F7/022 , H01L21/027 , G03F7/023 , G03F7/30
CPC分类号： G03F7/0226
摘要： A positive resist composition which comprises in admixture an alkali-soluble resin and, as a sensitizer, first and second quinone diazide sulfonic acid esters of a phenol compound, wherein(a) the first ester is a quinone diazide sulfonic acid diester of a phenol compound having not less than three hydroxyl groups which exhibits a pattern area that is not less than 40% of all pattern areas corresponding to the sensitizer in a high pressure liquid chromatography (HPLC) pattern measured with a primary detector using UV light having a wavelength of 254 nm, and(b) the second ester is a quinone diazide sulfonic acid ester that is a complete ester of a phenol compound having not less than two hydroxyl groups which exhibits a pattern area corresponding to not less than 5% and is less than 60% of all pattern areas corresponding to the sensitizer in the HPLC pattern.
摘要翻译：一种正性抗蚀剂组合物，其包含碱溶性树脂和作为敏化剂的酚化合物的第一和第二醌二叠氮磺酸酯，其中（a）第一酯是苯酚化合物的醌二叠氮磺酸二酯在使用波长为254的紫外光的主要检测器测量的高压液相色谱（HPLC）图案中，具有不小于3个羟基的图案面积不小于对应于敏化剂的所有图案区域的40％ nm，和（b）第二酯是醌二叠氮基磺酸酯，其是具有不少于2个羟基的酚化合物的完全酯，其显示对应于不小于5％且小于60％的图案面积，在HPLC图案中对应于敏化剂的所有图案区域。

5. 发明授权

US5080997A Process for preparing a positive resist composition by mixing the condensation product of a quinone diazide sulfonyl halogenide and a phenol with a resin solution without isolating the condensation product from the crude mixture 失效
标题翻译：通过混合二氢化亚油酸酯和酚醛树脂溶液的凝聚产物，不会从凝乳混合物分离凝结产物来制备阳性组合物的方法
公开(公告)号：US5080997A
公开(公告)日：1992-01-14
申请号：US446153
申请日：1989-12-05
申请人： Takeshi Hioki , Koji Kuwana , Jun Tomioka , Hirotoshi Nakanishi , Yasunori Uetani , Yukio Hanamoto , Fumio Oi
发明人： Takeshi Hioki , Koji Kuwana , Jun Tomioka , Hirotoshi Nakanishi , Yasunori Uetani , Yukio Hanamoto , Fumio Oi
IPC分类号： C08L61/04 , C08L61/06 , G03F7/022 , G03F7/023
CPC分类号： G03F7/023
摘要： A process for preparing a positive resist composition, which process includes the steps of condensation reacting a quinone diazide sulfonyl halogenide with a phenol compound, mixing a condensation reaction mixture with a solution of an alkali-soluble resin in a resist solvent and removing impurities from the mixture, whereby the overall processing time can be shortened.

6. 发明授权

US5861229A Radiation-sensitive positive resist composition comprising a 1,2-quinone diazide compound, an alkali-soluble resin and a polyphenol compound 失效
标题翻译：包含1,2-醌二叠氮化合物，碱溶性树脂和多酚化合物的辐射敏感性正性抗蚀剂组合物
公开(公告)号：US5861229A
公开(公告)日：1999-01-19
申请号：US948466
申请日：1992-09-22
申请人： Haruyoshi Osaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
发明人： Haruyoshi Osaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
IPC分类号： G03F7/022 , G03F7/023
CPC分类号： G03F7/0226 , G03F7/0236
摘要： A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:X--.alpha.--H (I)wherein x is a group of the formula: ##STR1## and .alpha. is a divalent group which comprises a repeating unit of the formula: ##STR2## in which n is a number of not less than 1; a, b, c, d, e and f are the same or different and a number of 0-3, provided that d+f is not less than 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or an aryl group, which resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.
摘要翻译：一种正性抗蚀剂组合物，其包含1,2-醌二叠氮化合物和含有下列通式的多酚化合物（I）的碱溶性树脂：X-α-H（I），其中x是下式的基团：并且α是包含下式的重复单元的二价基团：其中n是不小于1的数目：或 a，b，c，d，e和f相同或不同，数目为0-3，条件是d + f不小于1; R1，R2和R3相同或不同，C1-C18烷基，C1-C18烷氧基，羧基或卤原子; R4是氢原子，C1-C18烷基或芳基，其抗蚀剂组成对辐射敏感，并具有良好的灵敏度，分辨能力和耐热性的平衡。

7. 发明授权

US5456995A Radiation-sensitive positive resist composition 失效
标题翻译：辐射敏感正光刻胶组合物
公开(公告)号：US5456995A
公开(公告)日：1995-10-10
申请号：US224561
申请日：1994-04-07
申请人： Haruyoshi Ozaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
发明人： Haruyoshi Ozaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
IPC分类号： G03F7/022 , G03F7/023
CPC分类号： G03F7/0236 , G03F7/0226
摘要： A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer represented by the formula: ##STR1## wherein R is C.sub.1-18 or hydrogen, the composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.
摘要翻译：一种正性抗蚀剂组合物，其包含光敏1,2-醌二叠氮化合物，碱溶性树脂以结合成分和多酚化合物以控制由下式表示的显影剂中的溶解速率：位置对辐射敏感，具有良好的灵敏度平衡，分辨能力和耐热性。

8. 发明授权

US4812551A Novolak resin for positive photoresist 失效
标题翻译：用于正性光致抗蚀剂的酚醛清漆树脂
公开(公告)号：US4812551A
公开(公告)日：1989-03-14
申请号：US118041
申请日：1987-11-09
申请人： Fumio Oi , Haruyoshi Osaki , Akihiro Furuta , Yukikazu Uemura , Takao Ninomiya , Yasunori Uetani , Makoto Hanabata
发明人： Fumio Oi , Haruyoshi Osaki , Akihiro Furuta , Yukikazu Uemura , Takao Ninomiya , Yasunori Uetani , Makoto Hanabata
IPC分类号： G03C1/72 , C08G8/00 , C08G8/08 , G03F7/023 , C08G8/04
CPC分类号： C08G8/00 , C08G8/08 , G03F7/0236
摘要： A novolak resin for a positive photoresist is provided herein, which resin is produced by the addition condensation reaction of a phenol with formaldehyde. This novolak resin has improved heat resistant and sensitivity properties and the thickness retention of the novolak resins are very high. The novolak resins are characterized in that the area ratio of the gel permeation chromatographic pattern (GPC) as measured by the use of a UV(254 nm) detector, is as follows: a range wherein the molecular weight, calculated as polystyrene, is from 150 to less than 500, not including a phenol and the unreacted monomer, is from 8 to 35%, hereinafter referred to as an A region, the range wherein the molecular weight calculated as polystyrene is from 500 to less than 5000 is from 0 to 30%, hereinafter referred to as a B region, and the range wherein the molecular weight calculated as polystyrene exceeds 5000 is from 35 to 92%, hereinafter referred to as the C region, and wherein the ratio of the B region to the A region is 2.50 or less.
摘要翻译：本文提供了一种用于正性光致抗蚀剂的酚醛清漆树脂，该树脂通过苯酚与甲醛的加成缩合反应制备。该酚醛清漆树脂具有改善的耐热性和灵敏度性能，并且酚醛清漆树脂的厚度保持率非常高。酚醛清漆树脂的特征在于通过使用UV（254nm）检测器测量的凝胶渗透色谱图（GPC）的面积比如下：其中以聚苯乙烯计算的分子量来自 150〜小于500，不包括苯酚和未反应单体，为8〜35％，以下称为A区，其中以聚苯乙烯计算的分子量为500〜5000以下的范围为0〜 30％，以下称为B区，其中以聚苯乙烯计算的分子量超过5000的范围为35〜92％，以下称为C区，其中B区与A区的比例是2.50以下。

9. 发明授权

US5456996A Radiation-sensitive positive resist composition 失效
标题翻译：辐射敏感正光刻胶组合物
公开(公告)号：US5456996A
公开(公告)日：1995-10-10
申请号：US224563
申请日：1994-04-07
申请人： Haruyoshi Ozaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
发明人： Haruyoshi Ozaki , Fumio Oi , Yasunori Uetani , Makoto Hanabata , Takeshi Hioki
IPC分类号： G03F7/022 , G03F7/023
CPC分类号： G03F7/0236 , G03F7/0226
摘要： A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer having a molecular weight of not more than 550 and represented by the general formula: ##STR1## wherein a, b, c, d, e, and f are the same or different and a number of 0-3, provided that d+f is not less than 1, and provided that if b, d and f are 1, then at least one of a, c, and e is not 0; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or aryl group, wherein an amount of said 1,2-quinone diazide compound is from 5 to 100% by weight and an amount of said polyphenol compound is from 4 to 40% by weight based on the total weight of said alkali-soluble resin, wherein the resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.
摘要翻译：一种正性抗蚀剂组合物，其包含光敏1,2-醌二叠氮化合物，碱溶性树脂以结合成分和多酚化合物以控制分子量不大于550的显影剂中的溶解速率，并表示为其通式如下：其中a，b，c，d，e和f相同或不同，数为0-3，条件是d + f不小于1，条件是如果b ，d和f为1，则a，c和e中的至少一个不为0; R1，R2和R3相同或不同，C1-C18烷基，C1-C18烷氧基，羧基或卤原子; R4是氢原子，C1-C18烷基或芳基，其中所述1,2-醌二叠氮化合物的量为5〜100重量％，所述多酚化合物的量为4〜40体积％基于所述碱溶性树脂的总重量，其中抗蚀剂组合物对辐射敏感，并且具有良好的灵敏度平衡，分辨能力和耐热性。

10. 发明授权

US5413895A Positive resist composition comprising a quinone diazide sulfonic acid ester, a novolak resin and a polyphenol compound. 失效
标题翻译：包含醌二叠层磺酸酯，酚醛清漆树脂和多酚化合物的正型抗蚀剂组合物。
公开(公告)号：US5413895A
公开(公告)日：1995-05-09
申请号：US931316
申请日：1992-08-18
申请人： Jun Tomioka , Koji Kuwana , Hirotoshi Nakanishi , Yasunori Uetani , Ayako Ida
发明人： Jun Tomioka , Koji Kuwana , Hirotoshi Nakanishi , Yasunori Uetani , Ayako Ida
IPC分类号： G03F7/022 , H01L21/027 , G03F7/023 , G03F7/30
CPC分类号： G03F7/0226
摘要： A positive resist composition comprising an alkali-soluble resin containing a novolak resin which is obtained by a condensation reaction of a phenol compound and a carbonyl compound and has an area in a GPC pattern of a range in that a molecular weight as converted to polystyrene is not larger than 900 not exceeding 20% of a whole pattern area excluding the unreacted phenol compound, a quinonediazide compound and a polyphenol compound of the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a group: --OCOR.sub.3 in which R.sub.3 is an alkyl group or a phenyl group, x and y are independently an integer of 1 to 3, and m is an integer of 0 to 4, wherein a weight ratio of said polyphenol compound (I) to said alkali-soluble resin is from 3:10 to 5:10, which is excellent in heat resistance, sensitivity, resolution and a depth of focus and leaves no scum after development.
摘要翻译：含有通过酚化合物与羰基化合物的缩合反应得到的酚醛清漆树脂的碱溶性树脂的正型抗蚀剂组合物，其GPC图案的面积为转化为聚苯乙烯的分子量的范围为不大于900不超过除了未反应的酚化合物之外的整个图案区域的20％，醌二叠氮化合物和下式的多酚化合物：其中R 1和R 2独立地为氢原子，卤素原子，烷基，烷氧基或基团：其中R 3为烷基或苯基的-OCOR 3，x和y独立地为1〜3的整数，m为0〜4的整数，其中，所述多酚化合物（I）与所述碱溶性树脂的重量比为3:10〜5:10，耐热性，灵敏度，分辨率和焦深均优异，显影后无浮渣。

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