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    Compounds with acid-labile protective groups useful in positive-working radiation-sensitive mixtures
    32.
    发明授权
    Compounds with acid-labile protective groups useful in positive-working radiation-sensitive mixtures 失效
    具有酸性不稳定保护基的化合物可用于正性辐射敏感混合物

    公开(公告)号：US5356752A

    公开(公告)日：1994-10-18

    申请号：US920848

    申请日：1992-07-28

    申请人： Ivan Cabrera ,  Walter Spiess ,  Georg Pawlowski

    发明人： Ivan Cabrera ,  Walter Spiess ,  Georg Pawlowski

    IPC分类号： B01J27/055 ,  B01J31/08 ,  B01J31/24 ,  C07B61/00 ,  C07C68/06 ,  C07C69/96 ,  C07C205/43 ,  C07C233/69 ,  C07C255/54 ,  C07C309/73 ,  C07C311/24 ,  C09K9/02 ,  G03F7/004 ,  G03C1/492

    CPC分类号： G03F7/0045 ,  C07C69/96 ,  Y02P20/55

    摘要： Disclosed are compounds of the formula I ##STR1## in which X is a phenyl, [1]naphthyl or [2]naphthyl radical each substituted by at least one tert.-butoxycarbonyloxy group and, if appropriate, having one or more than one additional substituent,R.sup.1 is a hydrogen atom, a (C.sub.1 -C.sub.6)-alkyl radical, a (C.sub.6 -C.sub.10)-aryl radical or one of the radicals X andR.sup.2 and R.sup.3 are identical or different and are a (C.sub.1 -C.sub.12)-alkyl radical in which, if appropriate, up to three methylene groups are replaced by bridge members having at least one hetero atom, such as --O--, --S--, --NR.sup.4 --, --CO--, --CO--O--, --CO--NH--, --O--CO--NH--, --NH--CO--NH--, --CO--NH--CO--, --SO.sub.2 --, --SO.sub.2 --O-- or --SO.sub.2 --NH--, a (C.sub.3 -C.sub.12)-alkenyl, (C.sub.3 -C.sub.12)-alkynyl, (C.sub.4 -C.sub.12)-cycloalkyl, (C.sub.4 -C.sub.12)-cycloalkenyl or (C.sub.8 -C.sub.16)-aralkyl radical in which, if appropriate, up to three methylene groups of the aliphatic moiety are replaced by bridge members of the abovementioned type and which can be substituted in the aromatic moiety by fluorine, chlorine or bromine atoms or by (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, nitro, cyano or tert.-butoxycarbonyloxy groups,R.sup.4 being an acyl radical, especially a (C.sub.1 -C.sub.6)-alkanoyl radical.

    摘要翻译： 公开了式I的化合物，其中X是苯基，[1]萘基或[2]萘基，其各自被至少一个叔丁氧羰基氧基取代，并且如果合适，具有一个或多于一个另外的 取代基，R 1是氢原子，（C 1 -C 6） - 烷基，（C 6 -C 10） - 芳基或基团X和R 2和R 3中的一个相同或不同，并且是（C 1 -C 12） - 烷基，其中如果合适，最多三个亚甲基被具有至少一个杂原子的桥连构件替代，例如-O - ， - S - ， - NR 4 - ， - CO - ， - CO-O-， - CO-NH-，-O-CO-NH-，-NH-CO-NH-，-CO-NH-CO-，-SO2-，-SO2-O-或-SO2-NH-，（C3-C12 ） - 烯基，（C 3 -C 12） - 炔基，（C 4 -C 12） - 环烷基，（C 4 -C 12） - 环烯基或（C 8 -C 16） - 芳烷基，其中如果合适，最多三个亚烷基 部分被上述类型的桥连体取代，并且可以在芳族部分被氟，氯或溴原子取代，或被（C 1 -C 4） - 烷基 1，（C 1 -C 4） - 烷氧基，硝基，氰基或叔丁氧基羰基氧基，R 4是酰基，特别是（C 1 -C 6） - 烷酰基。

    Process for preparing resists
    35.
    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。

    Radiation sensitive composition
    37.
    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）。

    Photosensitive diazo and photopolymerizable recording material with a photosensitive diazo intermediate layer
    38.
    发明授权
    Photosensitive diazo and photopolymerizable recording material with a photosensitive diazo intermediate layer 失效
    光敏重氮和光聚合记录材料与感光重氮中间层

    公开(公告)号：US4956261A

    公开(公告)日：1990-09-11

    申请号：US403007

    申请日：1989-09-06

    申请人： Georg Pawlowski ,  Peter Lehmann

    发明人： Georg Pawlowski ,  Peter Lehmann

    IPC分类号： G03F7/095

    CPC分类号： G03F7/0955

    摘要： A photosensitive recording material with a layer base and a photosensitive layer, which essentially contains a diazonium salt polycondensation product, a polymeric binder which is insoluble in water and soluble in organic solvents and soluble or at least swellable in aqueous alkaline solutions, a polymerization initiator which forms free radicals when exposed to actinic radiation and a polymerizable ethylenically unsaturated compound containing at least one unsaturated group and having a boiling point at normal pressure of over 100.degree. C., wherein the recording material contains, between the photosensitive layer and the layer base, a photosensitive intermediate layer which essentially contains a diazonium salt polycondensation product and a polymeric binder which is insoluble in water and soluble in organic solvents and soluble or at least swellable in aqueous alkaline solutions.

    摘要翻译： 具有基层和感光层的光敏记录材料，其基本上含有重氮盐缩聚产物，不溶于水并且可溶于有机溶剂并且可溶或至少可溶于碱性水溶液的聚合物粘合剂，聚合引发剂 当暴露于光化辐射时形成自由基和含有至少一个不饱和基团并且在常压下沸点超过100℃的可聚合的烯属不饱和化合物，其中记录材料在感光层和层底之间包含， 感光中间层，其基本上含有重氮盐缩聚产物和聚合物粘合剂，其不溶于水并且可溶于有机溶剂，并且在碱性水溶液中可溶或至少可溶胀。

    Photosensitive mixture and photosensitive recording material produced therefrom with polymeric binder which is reaction product of (thio) phosphinic acidiso (thio) cyanate and active hydrogen containing polymer
    39.
    发明授权
    Photosensitive mixture and photosensitive recording material produced therefrom with polymeric binder which is reaction product of (thio) phosphinic acidiso (thio) cyanate and active hydrogen containing polymer 失效
    由（硫代）次膦酸异（硫代）氰酸酯和含活性氢聚合物的反应产物的聚合物粘合剂制备的感光混合物和感光记录材料

    公开(公告)号：US4839254A

    公开(公告)日：1989-06-13

    申请号：US47103

    申请日：1987-05-08

    申请人： Georg Pawlowski ,  Hans-Jerg Kleiner

    发明人： Georg Pawlowski ,  Hans-Jerg Kleiner

    IPC分类号： C08F2/48 ,  G03C1/72 ,  G03F7/021 ,  G03F7/035 ,  G03F7/038

    CPC分类号： G03F7/021 ,  G03F7/0388 ,  Y10S430/107 ,  Y10S430/109 ,  Y10S430/11

    摘要： A photosensitive mixture contains a photosensitive compound and a polymeric binder which s a reaction product of a compound represented by the formula ##STR1## wherein X and Y are the same or different, and each denotes oxygen or sulfur,R.sub.1 and R.sub.2 are the same or different, and each denotes an unsubstituted or substituted alkyl, cycloalkyl or alkoxy radical containing from 1 to 6 carbon atoms; an unsubstituted or substituted aryl or aryloxy radical containing from 6 to 10 carbon atoms; or, together with the phosphorus atom, a 5- or 6-membered heterocyclic ring which is unsubstituted or substituted or which carries a fused benzene ring,with a polymer containing active hydrogen. The novel binders used in the mixture can be easily prepared and yield photosensitive layers of good developability and developer resistance.

    摘要翻译： 感光性混合物含有感光性化合物和聚合物粘合剂，其为由式（I）表示的化合物与X和Y相同或不同的化合物的反应产物，各自表示氧或硫，R 1和R 2为 各自表示含有1至6个碳原子的未取代或取代的烷基，环烷基或烷氧基; 含有6至10个碳原子的未取代或取代的芳基或芳氧基; 或者与磷原子一起形成未被取代或取代或带有稠合苯环的5-或6-元杂环与含有活性氢的聚合物。 可以容易地制备混合物中使用的新型粘合剂，并产生良好的显影性和显影剂抗性的感光层。

    Composition for anti-reflective coating or radiation absorbing coating and compounds used in the composition
    40.
    发明授权
    Composition for anti-reflective coating or radiation absorbing coating and compounds used in the composition 有权
    用于组合物中的抗反射涂层或辐射吸收涂层和化合物的组合物

    公开(公告)号：US06803168B1

    公开(公告)日：2004-10-12

    申请号：US09237125

    申请日：1999-01-26

    申请人： Munirathna Padmanaban ,  Wen-Bing Kang ,  Hatsuyuki Tanaka ,  Ken Kimura ,  Georg Pawlowski

    发明人： Munirathna Padmanaban ,  Wen-Bing Kang ,  Hatsuyuki Tanaka ,  Ken Kimura ,  Georg Pawlowski

    IPC分类号： G03F7004

    CPC分类号： G03F7/091 ,  C08F220/34 ,  C08G18/2825 ,  C08G18/2865 ,  C08G18/728 ,  C08G18/8116 ,  C09D4/00 ,  C09D5/32 ,  G03F7/0045

    摘要： A composition for an anti-reflective coating or a radiation absorbing coating which can form an anti-reflective coating or a radiation absorbing coating having high absorption to exposed radiation in the range of 100 to 450 nm, no diffusion of photo-generated acid to anti-reflective coating and so on, no intermixing of resist and anti-reflective coating layer, good shelf-life stability, and good step coverage and novel compounds and polymers being preferably used in the composition are disclosed. The composition contains an acrylic or methacrylic compound or polymer with an isocyanate or thioisocyanate group bonded through an alkylene group to a side chain thereof or with an amino or hydroxyl group-containing organic chromophore which absorbs radiation in the range of 100 to 450 nm wavelength and is bonded, for example, through an alkylene group to the isocyanate or thioisocyanate group. Resist patters with high resolution are formed on a substrate. A composition for an anti-reflective coating or a radiation absorbing coating are applied on the substrate and baked to form an anti-reflective coating or a radiation absorbing coating layer. Then, a chemically amplified resist is coated thereon and after patternwize exposure, developed. During baking of the anti-reflective coating or radiation absorbing coating, hardening or curing of the coating takes place by the presence of the isocyanate or thioisocyanate group. On the other hand, the exposed radiation having wavelength in the range of 100 to 450 nm is absorbed by organic chromophore.

    摘要翻译： 用于抗反射涂层或辐射吸收涂层的组合物，其可以形成对100至450nm范围内的暴露辐射具有高吸收的抗反射涂层或辐射吸收涂层，而不会将光产生的酸扩散到抗 反射涂层等，公开了抗蚀剂和抗反射涂层的互相混合，良好的保质期稳定性和良好的阶梯覆盖率，并且组合物中优选使用的新型化合物和聚合物。 该组合物含有丙烯酸或甲基丙烯酸类化合物或具有通过亚烷基键合到其侧链上的异氰酸酯或硫代异氰酸酯基团或与吸收在波长为100至450nm范围内的辐射的含氨基或羟基的有机发色团的聚合物，以及 例如通过亚烷基键合到异氰酸酯或硫代异氰酸酯基团。 在基板上形成具有高分辨率的抗蚀剂图案。 将用于抗反射涂层或辐射吸收涂层的组合物施加在基材上并烘烤以形成抗反射涂层或辐射吸收涂层。 然后，将化学放大抗蚀剂涂覆在其上，并经过图案化曝光后显影。 在防反射涂层或辐射吸收涂层的烘烤期间，涂层的硬化或固化通过异氰酸酯或硫代异氰酸酯基团的存在进行。 另一方面，波长在100〜450nm的曝光的辐射被有机发色团吸收。