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    Process for preparing resists
    5.
    发明授权
    Process for preparing resists 有权
    抗蚀剂的制备方法

    公开(公告)号：US06686121B2

    公开(公告)日：2004-02-03

    申请号：US09824198

    申请日：2001-04-02

    申请人： Hiroshi Okazaki ,  Georg Pawlowski ,  Satoru Funato ,  Yoshiaki Kinoshita ,  Yuko Yamaguchi

    发明人： Hiroshi Okazaki ,  Georg Pawlowski ,  Satoru Funato ,  Yoshiaki Kinoshita ,  Yuko Yamaguchi

    IPC分类号： G03C173

    CPC分类号： G03F7/039 ,  C08F8/00 ,  C08F8/14 ,  C08F8/18 ,  C08F212/14 ,  C08F257/02 ,  C08F2800/20 ,  C08F2810/30 ,  C08L25/18 ,  C09D125/18 ,  G03F7/0045 ,  Y10S430/119 ,  C08F12/14 ,  C08F216/125 ,  C08F220/14 ,  C08F220/06 ,  C08F112/14

    摘要： A resist composition is prepared by reacting an alkali-soluble polymer having a phenolic hydroxyl or carboxyl groups with a vinyl ether compound in an aprotic solvent, such as propylene glycol monomethyl ether acetate, in the presence of an acid catalyst, suspending the reaction by the addition of a base, and directly adding a photoacid generator to the reaction solution. When a dialkyl dicarbonate is used in stead of the vinyl ether compound, a resist composition is prepared by carrying out the reaction in the presence of a basic catalyst and adding a photoacid generator directly to the reaction. Thus resist compositions can be prepared without isolating or purifying an alkali-soluble polymer which has been substituted by a catalytic reaction.

    摘要翻译： 抗蚀剂组合物通过使酸性催化剂存在下使非酚质子溶剂如丙二醇单甲醚乙酸酯中的具有酚羟基或羧基的碱溶性聚合物与乙烯基醚化合物反应来制备， 加入碱，并将光致酸产生剂直接加入到反应溶液中。 当使用二碳酸二烷基酯代替乙烯基醚化合物时，通过在碱性催化剂的存在下进行反应并直接向反应中加入光致酸产生剂制备抗蚀剂组合物。 因此，可以在不分离或纯化已经被催化反应取代的碱溶性聚合物的情况下制备抗蚀剂组合物。

    Positive-working radiation-sensitive mixture
    7.
    发明授权
    Positive-working radiation-sensitive mixture 失效
    正面工作的辐射敏感混合物

    公开(公告)号：US5843319A

    公开(公告)日：1998-12-01

    申请号：US902072

    申请日：1997-07-29

    申请人： Klaus Juergen Przybilla ,  Takanori Kudo ,  Seiya Masuda ,  Yoshiaki Kinoshita ,  Natsumi Suehiro ,  Munirathna Padmanaban ,  Hiroshi Okazaki ,  Hajime Endo ,  Ralph Dammel ,  Georg Pawlowski

    发明人： Klaus Juergen Przybilla ,  Takanori Kudo ,  Seiya Masuda ,  Yoshiaki Kinoshita ,  Natsumi Suehiro ,  Munirathna Padmanaban ,  Hiroshi Okazaki ,  Hajime Endo ,  Ralph Dammel ,  Georg Pawlowski

    IPC分类号： G03F7/004 ,  G03F7/039 ,  B01D15/00 ,  B01J39/00 ,  C02F1/42

    CPC分类号： G03F7/0045 ,  G03F7/039

    摘要： A process for producing a solution of a basic or non-basic sulfonium compound (A) of formulae II-V: ##STR1## wherein R.sup.5, R.sup.6 and R.sup.7 each independently represent a C.sub.1 -C.sub.18 alkyl, aryl or heteroaryl group or an aryl group mono-, di- or tri-substituted with an alkyl, an alkylaryl, an aryl, a halogen, an alkoxy, a phenoxy, a thiophenol, a phenylsulfonyl or a phenylsulphenyl; Y represents (CH.sub.2).sub.n (wherein n is 0 or 1), O or S; R.sup.8 and R.sup.9 represent a C.sub.1 -C.sub.4 alkyl, alkoxy or a halogen; R.sup.10 and R.sup.11 represent a C.sub.1 -C.sub.4 alkyl, alkoxy or a halogen; n is 5 or 6; and X.sub.2.sup.- represents a basic anion having a pK.sub.B value of -3 to +5; comprising the steps of: (a) dissolving a sulfonium salt (B) in a metal-ion free polar or non-polar solvent to form a solution, said sulfonium salt (B) being selected from said formulae II-V, wherein R.sup.5 to R.sup.11, Y and n of said sulfonium salt (B) have the sane meaning as above and X.sub.2.sup.- represents a non-nucleophilic anion; (b) contacting said solution for a sufficient amount of time with a basic ion-exchange resin having a quaternary ammonium group to replace the anion of (B) with a hydroxide ion and to form a sulfonium hydroxide solution; (c) separating said sulfonium hydroxide solution from the resin; and optionally (d) adding an active hydrogen containing compound or its base-labile precursor to said sulfonium hydroxide solution to yield a solution of the sulfonium compound (A) wherein X.sub.2.sup.- represents a basic anion other than a hydroxy ion.

    摘要翻译： 制备式II-V的碱性或非碱性锍化合物（A）的溶液的方法：[SR5R6R7] + X2-Ⅱ其中R5，R6和R7各自独立地 独立地表示C1-C18烷基，芳基或杂芳基或被烷基，烷基芳基，芳基，卤素，烷氧基，苯氧基，苯硫酚，苯基磺酰基或苯基磺酰基单 - ，二 - 或三 - 取代的芳基 苯基磺酰基; Y表示（CH 2）n（其中n为0或1），O或S; R8和R9代表C1-C4烷基，烷氧基或卤素; R10和R11表示C1-C4烷基，烷氧基或卤素; n为5或6; X2-表示pKB值为-3〜+5的碱性阴离子; 包括以下步骤：（a）将锍盐（B）溶解在无金属离子的极性或非极性溶剂中以形成溶液，所述锍盐（B）选自所述式II-V，其中R5至 所述锍盐（B）的R 11，Y和n具有如上所述的正义，X2-表示非亲核阴离子; （b）用具有季铵基团的碱性离子交换树脂将所述溶液接触足够的时间以用氢氧根离子代替（B）的阴离子并形成氢氧化锍溶液; （c）从树脂中分离出氢氧化锍溶液; 和任选地（d）在所述氢氧化锍溶液中加入含活性氢的化合物或其碱不稳定的前体，得到其中X2代表羟基离子以外的碱性阴离子的锍化合物（A）的溶液。

    Radiation sensitive composition
    8.
    发明授权
    Radiation sensitive composition 失效
    辐射敏感组合物

    公开(公告)号：US5738972A

    公开(公告)日：1998-04-14

    申请号：US864375

    申请日：1997-05-28

    申请人： Munirathna Padmanaban ,  Natsumi Suehiro ,  Yoshiaki Kinoshita ,  Satoru Funato ,  Seiya Masuda ,  Hiroshi Okazaki ,  Georg Pawlowski

    发明人： Munirathna Padmanaban ,  Natsumi Suehiro ,  Yoshiaki Kinoshita ,  Satoru Funato ,  Seiya Masuda ,  Hiroshi Okazaki ,  Georg Pawlowski

    IPC分类号： G03F7/00 ,  G03F7/004 ,  G03F7/033 ,  G03F7/039 ,  G03F7/085 ,  H01L21/027 ,  G03F7/38

    CPC分类号： G03F7/0045 ,  Y10S430/106

    摘要： A chemically amplified resist material comprising: a) a homopolymer or a copolymer of hydroxystyrene or hydroxystyrene partly protected by a group sensitive to an acid such as a tetrahydropyranyl or t-butoxycarbonyl group, b) a dissolution inhibitor such as poly(N,O-acetal) or phenol or bisphenol protected by a group cleavable with an acid, c) a photosensitive compound capable of generating an acid upon exposure, d) a base capable of degrading upon radiation to regulate the line width in a period between the exposure step and the processing steps after exposure, e) a low-molecular weight phenolic or polyphenolic compound having a structure represented by the following general formula or a mixture of the phenolic or polyphenolic compounds: ##STR1## where n is an integer of 1 to 5, m is an integer of 0 to 4, n+m.ltoreq.5, and p is an integer of 1 to 10, each R is a C.sub.1 -C.sub.12 alkyl group or an unsubstituted or substituted cycloalkyl group or a C.sub.1 -C.sub.5 hydroxyalkyl group, provided that hydrogen atoms may be substituted with a halogen atom and, when m is not less than 2, each R may be the same or different; A represents a hydrocarbon atomic grouping, having a valence of p, including an unsubstituted or substituted C.sub.1 -C.sub.100 alicyclic, chain aliphatic, or aromatic hydrocarbon or a combination thereof with the carbon atoms being optionally substituted with an oxygen atom, provided that when p is 1, A may represent a hydrogen atom and, when p is 2, A may represent --S--, --SO--, --SO.sub.2 --, --O--, --CO--, or a direct bond, and f) a solvent for dissolving the components a) to e).

    摘要翻译： 一种化学放大抗蚀剂材料，包括：a）部分由对酸如四氢吡喃基或叔丁氧基羰基敏感的基团部分保护的羟基苯乙烯或羟基苯乙烯的均聚物或共聚物，b）溶解抑制剂如聚（N， 乙缩醛）或苯酚或双酚被被一个酸可裂解的基团保护，c）一种能够在暴露时产生酸的感光性化合物，d）能够在辐射下降解以在曝光步骤和 曝光后的处理步骤，e）具有由以下通式表示的结构的低分子量酚或多酚化合物或酚类或多酚化合物的混合物：n为0〜4的整数，n + m = 5 ，p为1〜10的整数，R为C1-C12烷基或未取代或取代的环烷基或C1-C5羟烷基，条件是氢原子可被卤素原子取代， en不小于2，每个R可以相同或不同; A表示具有p价的烃原子团，包括未取代或取代的C1-C100脂环族，链脂族或芳族烃或其任选被氧原子取代的碳原子的组合，条件是当p为 1中，A可以表示氢原子，当p为2时，A可以表示-S-，-SO-，-SO2-，-O-，-CO-或直接键，f）溶解溶剂 组件a）至e）。

    Radiation-sensitive sulfonic acid esters and their use
    9.
    发明授权
    Radiation-sensitive sulfonic acid esters and their use 失效
    辐射敏感磺酸酯及其用途

    公开(公告)号：US5442061A

    公开(公告)日：1995-08-15

    申请号：US139017

    申请日：1993-10-21

    申请人： Georg Pawlowski ,  Horst Roeschert ,  Walter Spiess ,  Klaus-Juergen Przybilla

    发明人： Georg Pawlowski ,  Horst Roeschert ,  Walter Spiess ,  Klaus-Juergen Przybilla

    IPC分类号： G03F7/004 ,  C07D251/24 ,  C08L61/06 ,  C08L61/28 ,  C09D161/06 ,  G03F7/00 ,  G03F7/029 ,  G03F7/038 ,  H01L21/027

    CPC分类号： G03F7/038 ,  C07D251/24 ,  C09D161/06 ,  C08L61/06 ,  C08L61/28 ,  Y10S430/111 ,  Y10S430/12 ,  Y10S430/123

    摘要： Sulfonic acid esters of 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine are disclosed. Also disclosed is a negative-working radiation-sensitive mixture containing such a compound in combination with a compound containing at least two acid-crosslinkable groups, and a water-insoluble polymeric binder which is soluble or at least swellable in aqueous alkaline solutions. The esters are esters of a sulfonic acid or sulfonic acids of the formula R--SO.sub.3 H or R'(--SO.sub.3 H).sub.2 with 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine of the formulae I and/or II ##STR1## where R is an optionally further substituted (C.sub.1 -C.sub.10)alkyl, (C.sub.5 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl-(C.sub.1 -C.sub.10)alkyl or (C.sub.3 -C.sub.9)heteroaryl radical, R' is an optionally substituted (C.sub.1 -C.sub.10)alkylene, (C.sub.6 -C.sub.10)arylene or (C.sub.3 -C.sub.9)heteroarylene radical, and n may be 1 or 2. The radiation-sensitive mixture according to the invention is remarkable for a high resolution and a high sensitivity over a wide spectral range and can be used to produce a radiation-sensitive recording material suitable for producing photoresists, electronic components, or printing plates, or for chemical milling.

    摘要翻译： 公开了2,4-双三氯甲基-6-（单 - 或二羟基苯基）-1,3,5-三嗪的磺酸酯。 还公开了含有这种化合物与含有至少两个酸可交联基团的化合物的负性辐射敏感性混合物，以及在碱性水溶液中可溶或至少可溶胀的水不溶性聚合物粘合剂。 酯是式R-SO 3 H或R'（-SO 3 H）2的磺酸或磺酸与2,4-二三氯甲基-6-（单或二羟苯基）-1,3,5-三嗪的酯 （C 1 -C 10）烷基，（C 5 -C 10）环烷基，（C 6 -C 10）芳基，（C 6 -C 10）芳基 - （C 1 -C 10）烷基或（C 1 -C 10） C3-C9）杂芳基，R'是任选取代的（C 1 -C 10）亚烷基，（C 6 -C 10）亚芳基或（C 3 -C 9）亚杂芳基，n可以是1或2.根据 本发明对于在宽光谱范围内的高分辨率和高灵敏度是显着的，并且可用于生产适用于生产光刻胶，电子部件或印刷版或用于化学研磨的辐射敏感记录材料。