公开(公告)号：US06376152B2

公开(公告)日：2002-04-23

申请号：US09775620

申请日：2001-02-05

申请人： Yasumasa Kawabe ,  Shinichi Kanna ,  Fumiyuki Nishiyama

发明人： Yasumasa Kawabe ,  Shinichi Kanna ,  Fumiyuki Nishiyama

IPC分类号： G03F7004

CPC分类号： G03F7/0045 ,  G03F7/039 ,  Y10S430/106 ,  Y10S430/12

摘要： A positive photoresist composition comprises (A) a compound which generates an acid upon irradiation with an actinic ray or radiation, (B) a resin which is insoluble or sparingly soluble in alkali but becomes soluble in alkali by the action of an acid, and (C) a nitrogen-containing compound containing at least one partial structure represented by formula (I) shown below in its molecule: The positive photoresist composition of the present invention is suitable for exposure to a far ultraviolet ray, particularly a KrF excimer laser beam, improved in line edge roughness and also excellent in sensitivity, resolution, depth of focus and resist profile.

摘要翻译： 正型光致抗蚀剂组合物包含（A）在用光化学射线或辐射照射时产生酸的化合物，（B）不溶于或微溶于碱但通过酸作用而溶于碱的树脂和（ C）在其分子中含有至少一种由式（I）表示的部分结构的含氮化合物：本发明的正性光致抗蚀剂组合物适用于暴露于远紫外线，特别是KrF准分子激光束， 线边缘粗糙度提高，灵敏度，分辨率，聚焦深度和抗蚀剂轮廓优异。

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：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。

公开(公告)号：US5360692A

公开(公告)日：1994-11-01

申请号：US70795

申请日：1993-06-03

申请人： Yasumasa Kawabe ,  Kazuya Uenishi ,  Tadayoshi Kokubo

发明人： Yasumasa Kawabe ,  Kazuya Uenishi ,  Tadayoshi Kokubo

IPC分类号： G03F7/004 ,  C07D249/20 ,  C07D403/10 ,  G03F7/022 ,  G03F7/023 ,  G03F7/09 ,  H01L21/027 ,  H01L21/30 ,  G03C1/61

CPC分类号： C07D403/10 ,  C07D249/20 ,  G03F7/0226 ,  G03F7/091

摘要： There is disclosed a positive type photoresist composition comprising an alkali-soluble resin, a compound having a 1,2-naphthoquinonediazido group, and at least one light absorbing agent selected from the group consisting of the compounds represented by the following formulae [I] and [II], the content of said light absorbing agent being in the range of 0.1 to 10% by weight based on the total solid content of the composition: ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkoxy group, an acyl group, or an aryl group; Y represents a single bond, an alkylene group, --O--, --S--, --SO.sub.2 --or ##STR2## R represents a hydrogen atom, an alkyl group, or an aralkyl group; m represents an integer from 1 to 3; and n represents an integer from 1 to 4. The content of light absorbing agent in said composition is in the range of from 0.3% by weight to 5% by weight, based on the total solid content of the composition.

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，具有1,2-萘醌二叠氮基的化合物和至少一种选自由下式[I]和 [II]中，所述光吸收剂的含量相对于组合物的总固体成分为0.1〜10重量％的范围：其中，X表示氢原子 卤素原子，烷基，芳烷基，烷氧基，酰基或芳基; Y表示单键，亚烷基，-O - ， - S - ， - SO 2 - 或R 2表示氢原子，烷基或芳烷基。 m表示1〜3的整数， n表示1〜4的整数。所述组合物中的光吸收剂含量为组合物总固体成分的0.3〜5重量％。

公开(公告)号：US4894311A

公开(公告)日：1990-01-16

申请号：US113951

申请日：1987-10-29

申请人： Kazuya Uenishi ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

发明人： Kazuya Uenishi ,  Yasumasa Kawabe ,  Tadayoshi Kokubo

IPC分类号： G03C1/72 ,  G03F7/022 ,  H01L21/027 ,  H01L21/30

CPC分类号： G03F7/022

摘要： A positive-working photoresist composition containing an alkali-soluble novolak resin and a photosensitive compound represented by the formula ##STR1## wherein D.sub.1 and D.sub.2, which may be the same or different, each represents a 1,2-naphthoquinonediazido-5-sulfonyl group or a 1,2-naphthoquinonediazido-4-sulfonyl group; R.sub.1 and R.sub.2, which may be the same or different, each represents an alkoxy group, or an alkyl ester group; and a, b, c, and d each is 0 or an integer from 1 to 5, provided that (a+b).gtoreq.1 and (c+d).gtoreq.1.The photoresist composition is excellent in sensitivity and resolving power and forms a resist pattern having good sectional shape and high heat resistance on, for example, a semiconductor. The photoresist composition is also applicable for forming a resist pattern having a line width of less than 1 .mu.m.

摘要翻译： 含有碱溶性酚醛清漆树脂和式（I）表示的光敏化合物的正性光致抗蚀剂组合物，其中D1和D2可以相同或不同，表示1,2-萘醌二叠氮基-5 磺酰基或1,2-萘醌二叠氮基-4-磺酰基; R 1和R 2可以相同或不同，各自表示烷氧基或烷基酯基; 并且a，b，c和d各自为0或1至5的整数，条件是（a + b）> / = 1和（c + d）> / = 1。 光致抗蚀剂组合物的灵敏度和分辨能力优异，并且在例如半导体上形成具有良好截面形状和高耐热性的抗蚀剂图案。 光致抗蚀剂组合物也可用于形成线宽小于1μm的抗蚀剂图案。

公开(公告)号：US4863828A

公开(公告)日：1989-09-05

申请号：US145862

申请日：1988-01-20

申请人： Yasumasa Kawabe ,  Kazuya Uenishi ,  Tadayoshi Kokubo

发明人： Yasumasa Kawabe ,  Kazuya Uenishi ,  Tadayoshi Kokubo

IPC分类号： G03C1/72 ,  G03F7/022

CPC分类号： G03F7/0226

摘要： A positive-working photoresist composition is disclosed, which comprises a light-sensitive substance of 1,2-naphthoquinonediazide-4- and/or -5-sulfonate of 2,3,4,3',4',5'-hexahydroxybenzophenone and an alkali-soluble novolak resin dissolved in ethyl lactate or methyl lactate.

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。

公开(公告)号：US5948587A

公开(公告)日：1999-09-07

申请号：US713997

申请日：1996-09-19

申请人： Yasumasa Kawabe ,  Shiro Tan

发明人： Yasumasa Kawabe ,  Shiro Tan

IPC分类号： G03F7/023 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0236

摘要： Provided is a positive working photoresist composition comprising (A) an alkali-soluble novolak resin obtained by condensation reaction of a mixture of phenols, which are constituted of specified proportions of m-cresol and two kinds of specific phenols, with an aldehyde and having a Mw/Mn ratio of from 1.5 to 4.0 (wherein Mw stands for a weight-average molecular weight, and Mn stands for a number-average molecular weight); (B) a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic acid ester as a photosensitive material; and (C) a low molecular weight compound having from 12 to 50 carbon atoms per molecule and from 2 to 8 phenolic hydroxy groups per molecule.

摘要翻译： 提供一种正性光致抗蚀剂组合物，其包含（A）通过由特定比例的间甲酚和两种特定酚构成的酚的混合物与醛缩合反应得到的碱溶性酚醛清漆树脂，并且具有 Mw / Mn比为1.5〜4.0（Mw表示重均分子量，Mn表示数均分子量）。 （B）作为感光材料的1,2-萘醌二叠氮化物-5-（和/或-4-）磺酸酯; 和（C）每分子具有12至50个碳原子且每分子具有2至8个酚羟基的低分子量化合物。

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。

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。