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公开(公告)号：US5629128A
公开(公告)日：1997-05-13
申请号：US531081
申请日：1995-09-20
IPC分类号： G03F7/022 , H01L21/027 , G03F7/023
CPC分类号： G03F7/022
摘要： A positive photoresist composition is described, which comprises an alkali-soluble resin and 1,2-naphthoquinone-diazido-5-(and/or -4-)sulfonate of a polyhydroxy compound represented by the following formula (I): ##STR1## wherein R.sub.1 to R.sub.11 are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxyl group, an acyl group or a cycloalkyl group, provided that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group; A represents -CH(R.sub.12)-, in which R.sub.12 represents a hydrogen atom or an alkyl group; and m represents 2 or 3.
摘要翻译： 描述了一种正型光致抗蚀剂组合物，其包含由下式（I）表示的多羟基化合物的碱溶性树脂和1,2-萘醌 - 二叠氮基-5-（和/或-4-）磺酸盐：
（I）其中R 1至R 11相同或不同，并且各自表示氢原子，卤素原子，烷基，芳基，烷氧基，酰基或环烷基，条件是R 1至R 11中的至少一个 R11为环烷基; A表示-CH（R 12） - ，其中R 12表示氢原子或烷基; m表示2或3。 -
公开(公告)号：US06596458B1
公开(公告)日：2003-07-22
申请号：US09563436
申请日：2000-05-03
IPC分类号： G03F7039
CPC分类号： G03F7/0397 , G03F7/0045 , Y10S430/111
摘要： Disclosed is a positive-working photoresist composition having reduced development defects, and excellent in resist pattern profiles and in the resolving power of contact holes, which comprises (i) a compound generating an acid by irradiation of active light or radiation, and (ii) a resin containing repeating units of at least one kind selected from the group consisting of (a) repeating units having alkali-soluble groups each protected with at least one group selected from the group consisting of groups containing alicyclic hydrocarbon structures represented by specific general formulas (pI) to (pVI), (b) repeating units represented by specific general formula (II) and (c) repeating units represented by specific general formulas (III-a) to (III-d), and decomposed by the action of an acid to increase the solubility of the resin into an alkali.
摘要翻译： 公开了具有减少的显影缺陷，抗蚀剂图案轮廓和接触孔分辨能力优异的正性光致抗蚀剂组合物，其包括（i）通过活性光或辐射的照射产生酸的化合物，和（ii） 含有重复单元的树脂，所述重复单元选自（a）具有碱溶性基团的重复单元，各自被至少一个选自由特定通式表示的脂环族烃结构的基团所选择的基团保护的基团 pI）至（pVI），（b）由特定通式（II）表示的重复单元和（c）由特定通式（III-a）至（III-d）表示的重复单元，并通过 酸以增加树脂在碱中的溶解度。
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公开(公告)号：US06699635B1
公开(公告)日：2004-03-02
申请号：US09471007
申请日：1999-12-23
IPC分类号： G03F7004
CPC分类号： G03F7/0048 , G03F7/0397 , Y10S430/106
摘要： A positive photosensitive composition suitable for resist pattern formation under exposure to far ultraviolet light of wavelengths of 250 nm or shorter, particularly 220 nm or shorther, comprising: (A) a resin comprising constitutional repeating units wherein particular ring structures are present and having groups capable of decomposing under the action of an acid to cause an increase of the solubility in an alkali developer, (B) a photo-acid generator capable of generating an acid upon irradiation with actinic rays or radiation, and (C) a fluorine-containing surfactant, a silicon-containing surfactant or a mixture thereof.
摘要翻译： 适合于在暴露于波长为250nm或更短，特别是220nm或更短的远紫外光下的抗蚀剂图案形成的正性感光性组合物，其包含：（A）包含结构重复单元的树脂，其中存在特定的环结构并具有基团 在酸的作用下分解，导致碱显影剂溶解度的增加，（B）能够在用光化学射线或辐射照射时产生酸的光酸发生剂，（C）含氟表面活性剂 ，含硅表面活性剂或其混合物。
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公开(公告)号：US5609982A
公开(公告)日：1997-03-11
申请号：US357748
申请日：1994-12-16
CPC分类号： G03F7/022
摘要： The present invention provides a positive-working photoresist composition comprising an alkali-soluble resin and a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic ester of a specific water-insoluble alkali-soluble low molecular compound, wherein the high-performance liquid chromatography of the ester with an ultraviolet ray at 254 nm shows that the patterns corresponding to the diester components and complete ester component of the ester each fall within the specific range and a positive-working photoresist composition comprising a water-insoluble alkali-soluble resin, a water-insoluble alkali-soluble low molecular compound, and an ionization-sensitive radioactive compound which comprises a mixture of a naphthoquinone-diazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having three phenolic hydroxyl groups as an ionization-sensitive radioactive compound (A) and a naphthoquinonediazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having four phenolic hydroxyl groups as an ionization-sensitive radioactive compound (B) in an amount of 30% or more by weight based on the total amount of the ionization-sensitive radioactive compound.
摘要翻译： 本发明提供一种正性光致抗蚀剂组合物，其包含碱溶性树脂和特定的水不溶性碱溶性低分子化合物的1,2-萘醌二叠氮化物-5-（和/或-4-）磺酸酯，其中 使用254nm紫外线的酯的高效液相色谱显示对应于酯的二酯组分和完全酯组分的图案分别落在特定范围内，并且包含非水溶性的正性光致抗蚀剂组合物 碱溶性树脂，水不溶性碱溶性低分子化合物和电离敏感性放射性化合物，其包含具有三个酚羟基的水不溶性碱溶性低分子化合物的萘醌二叠氮烷磺酸二酯的混合物作为 电离敏感的放射性化合物（A）和不溶于水的碱溶性低分子化合物的萘醌二叠氮化物二酯 具有基于电离敏感性放射性化合物的总量为30重量％以上的量的四个酚羟基作为电离敏感性放射性化合物（B）的量。
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公开(公告)号：US07214465B2
公开(公告)日：2007-05-08
申请号：US10338737
申请日：2003-01-09
申请人： Hajime Nakao , Yasumasa Kawabe , Toru Fujimori , Kunihiko Kodama
发明人： Hajime Nakao , Yasumasa Kawabe , Toru Fujimori , Kunihiko Kodama
IPC分类号： G03F7/004
CPC分类号： G03F7/0045 , G03F7/0395 , G03F7/0397 , Y10S430/106 , Y10S430/111 , Y10S430/122 , Y10S430/123
摘要： A positive photosensitive composition comprising (A1) a compound that generates an aromatic sulfonic acid substituted with at least one fluorine atom and/or a group having at least one fluorine atom upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a compound that has at least three hydroxy or substituted hydroxy groups and at least one cyclic structure or (A2) an onium salt of an alkanesulfonic acid in which the α-position of the sulfonic acid is not substituted with a fluorine atom and/or an onium salt of a carboxylic acid.
摘要翻译： 一种正型感光性组合物，其包含（A1）在光化射线或辐射照射时产生被至少一个氟原子取代的芳香族磺酸和/或具有至少一个氟原子的基团的化合物，（B）具有 单环或多环脂环族烃结构，并通过酸的作用分解以提高在碱性显影液中的溶解度，（C）具有至少三个羟基或取代羟基和至少一个环状结构的化合物或（A2 ）其中磺酸的α-位没有被氟原子和/或羧酸的鎓盐取代的烷基磺酸的鎓盐。
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公开(公告)号：US5652081A
公开(公告)日：1997-07-29
申请号：US708676
申请日：1996-09-05
申请人： Shiro Tan , Shinji Sakaguchi , Yasumasa Kawabe
发明人： Shiro Tan , Shinji Sakaguchi , 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 an alkali-soluble resin and a 1,2-quinonediazide compound, with the resin being a novolak resin obtained by the condensation reaction of monomers comprising specified phenol compounds with formaldehyde.
摘要翻译： 提供了一种正性光致抗蚀剂组合物，其包含碱溶性树脂和1,2-醌二叠氮化合物，该树脂是通过使特定的酚化合物与甲醛的单体的缩合反应获得的酚醛清漆树脂。
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公开(公告)号：US5523396A
公开(公告)日：1996-06-04
申请号：US531861
申请日：1995-09-21
申请人： Kenichiro Sato , Yasumasa Kawabe , Toshiaki Aoai
发明人： Kenichiro Sato , Yasumasa Kawabe , Toshiaki Aoai
IPC分类号： B01J31/02 , C07C303/28 , C07C309/47 , C07C309/69 , C07C309/71 , C07C309/76 , G03F7/022 , H01L21/027 , G03F7/023
CPC分类号： C07C303/28 , G03F7/022 , C07C2101/14
摘要： A process for synthesizing a quinonediazide ester is disclosed in which the esterification reaction of a polyhydroxy compound with 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonyl chloride is carried out in the presence of a base catalyst comprising a basic compound represented by formula (I) or (II): ##STR1## wherein R.sub.1 to R.sub.15 are defined in the disclosure. A positive working photoresist containing the ester is also disclosed. The process is capable of highly selectively yielding the desired photosensitive material containing specific unreacted hydroxyl group(s). The photoresist has high resolving power with reduced film thickness dependence of the resolving power, is less apt to leave a development residue, and has excellent storage stability for prolonged period of time.
摘要翻译： 公开了一种用于合成醌二叠氮化物酯的方法，其中多羟基化合物与1,2-萘醌二叠氮化物-5-（和/或-4-）磺酰氯的酯化反应在含有碱 式（I）或（II）表示的化合物：其中R 1至R 15在本公开内容中定义。 还公开了含有酯的正性工作光致抗蚀剂。 该方法能够高选择性地产生含有特定未反应羟基的所需光敏材料。 光致抗蚀剂具有高的分辨能力，降低膜分离能力的依赖性，更不容易留下显影残留物，并且在长时间内具有优异的储存稳定性。
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公开(公告)号：US6159656A
公开(公告)日：2000-12-12
申请号：US344141
申请日：1999-06-24
申请人： Yasumasa Kawabe , Kenichiro Sato , Toshiaki Aoai
发明人： Yasumasa Kawabe , Kenichiro Sato , Toshiaki Aoai
CPC分类号： G03F7/0045 , G03F7/0048 , G03F7/039 , Y10S430/106
摘要： The present invention provides a positive photosensitive resin composition which, when exposed to far ultraviolet rays, in particular, ArF excimer laser light, shows excellent performances especially with respect to the residual film ratio, resist profile, resolution, and dry-etching resistance and does not pose the problem of development defects. The positive photosensitive resin composition comprising:(A) a compound which generates an acid upon irradiation with actinic rays,(B) a polymer having specific structures represented by formula (Ia), (Ib), (Ic) or (Id) defined in the specification,(C) a nitrogen-containing basic compound, and(D) at least one of a fluorine type surfactant and a silicone type surfactant.
摘要翻译： 本发明提供一种正型感光性树脂组合物，特别是在远紫外线照射ArF准分子激光时，表现出优异的性能，特别是在残留膜比，抗蚀剂轮廓，分辨率和耐干蚀刻性方面，特别是 不构成发展缺陷的问题。 正型感光性树脂组合物，其包含：（A）在光化射线照射时产生酸的化合物，（B）具有由式（Ia），（Ib），（Ic）或（Id）表示的特定结构的聚合物， （C）含氮碱性化合物和（D）氟型表面活性剂和硅氧烷型表面活性剂中的至少一种。
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公开(公告)号：US5534382A
公开(公告)日：1996-07-09
申请号：US411209
申请日：1995-03-27
申请人： Yasumasa Kawabe , Kenichiro Sato
发明人： Yasumasa Kawabe , Kenichiro Sato
IPC分类号： G03F7/022 , H01L21/027 , G03F7/021 , G03F7/30
CPC分类号： G03F7/022
摘要： Disclosed is a positive photoresist composition comprising an alkali-soluble resin and the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonate acid ester of a polyhydroxy compound represented by formula (I): ##STR1## wherein R.sub.1 to R.sub.3 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, or an alkoxy group; and m, n and o each represent an integer of from 1 to 3. The photoresist composition has a high resolving power and a less layer thickness reliance of the resolving power, and a wide development latitude, is reluctant to form a development residue, and further has a very excellent storage stability, and does not deposit the photosensitive material and does not form microgels, i.e., shows no increase in the particles, with the passage of time.
摘要翻译： 公开了一种正型光致抗蚀剂组合物，其包含碱溶性树脂和由式（I）表示的多羟基化合物的1,2-萘醌二叠氮基-5-（和/或-4-）磺酸酯： 其中R 1至R 3可以相同或不同，并且各自表示氢原子，卤素原子，羟基，烷基或烷氧基; m，n和o各自表示1〜3的整数。光致抗蚀剂组合物具有高的分辨能力和更小的层厚依赖分辨能力，并且广泛的开发范围不愿形成显影残渣， 进一步具有非常优异的储存稳定性，并且不沉积感光材料并且不形成微凝胶，即随着时间的推移，不显示颗粒的增加。
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公开(公告)号：US5529881A
公开(公告)日：1996-06-25
申请号：US404985
申请日：1995-03-16
申请人： Yasumasa Kawabe , Kenichiro Sato , Toshiaki Aoai , Kazuya Uenishi
发明人： Yasumasa Kawabe , Kenichiro Sato , Toshiaki Aoai , Kazuya Uenishi
IPC分类号： G03F7/022 , G03F7/039 , H01L21/027 , G03F7/023 , G03F7/30
CPC分类号： G03F7/022
摘要： A positive photoresist composition for super fine working is disclosed, which comprises (a) an alkali-soluble resin and (b) as a photosensitive compound the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid ester of a polyhydroxy compound represented by formula (I) or (II), wherein in a high-speed liquid chromatography measured using a ultraviolet ray of 254 nm, the pattern of the diester component and the pattern of the complete ester component of said 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid of the polyhydroxy compound shown by formula (I) or (II) are at least 50% and less than 40%, respectively, of the whole pattern areas; ##STR1## wherein R.sub.1 to R.sub.11, which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group, and R.sub.12 to R.sub.22, which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a cycloalkyl group, with the proviso that at least one of R.sub.12 to R.sub.22 is a cycloalkyl group. The photoresist composition has a high resolving power and a less layer thickness reliance of the resolving power, and a wide development latitude, is reluctant to form a development residue, and further has a very excellent storage stability, and does not deposit the photosensitive material and does not form microgels with the passage of time.
摘要翻译： 公开了一种用于超细加工的正性光致抗蚀剂组合物，其包含（a）碱溶性树脂和（b）作为光敏化合物的1,2-萘醌二叠氮基-5-（和/或-4-）磺酸酯 由式（I）或（II）表示的多羟基化合物，其中在使用254nm的紫外线测量的高速液相色谱中，所述二酯组分的图案和所述1,2的完全酯组分的图案 式（I）或（II）所示的多羟基化合物的萘醌二叠氮基-5-（和/或-4-）磺酸分别为整个图案区域的至少50％且小于40％; 1， 其可以相同或不同，各自表示氢原子，卤素原子，烷基，烷氧基或环烷基，条件是R 1至R 11中的至少一个为环烷基，R 12至 R 22可以相同或不同，各自表示氢原子，卤素原子，烷基，烷氧基，o 环烷基，条件是R12至R22中的至少一个为环烷基。 光致抗蚀剂组合物具有高的分辨能力和较小的层厚度的分辨能力依赖性，并且广泛的开发范围不愿形成显影残留物，并且还具有非常优异的储存稳定性，并且不沉积感光材料和 随着时间的推移不会形成微凝胶。
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