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    Acid labile dissolution inhibitors and positive- and negative-acting photosensitive composition based thereon
    1.
    发明授权
    Acid labile dissolution inhibitors and positive- and negative-acting photosensitive composition based thereon 失效
    酸性溶解抑制剂和基于其的阳性和阴性作用的感光性组合物

    公开(公告)号：US5210003A

    公开(公告)日：1993-05-11

    申请号：US756631

    申请日：1991-09-09

    申请人： Ulrich Schadeli

    发明人： Ulrich Schadeli

    IPC分类号： C07D309/10 ,  G03C1/73 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

    CPC分类号： C07D309/10 ,  G03F7/0045 ,  Y10S430/106

    摘要： Non-polymeric compounds which contain at least one aromatic ring system carrying one or more one or more tetrahydropyranyloxy substituents of formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl, cycloalkyl, aryl, alkoxy or aryloxy,R.sub.2 is hydrogen, alkyl, cycloalkyl or aryl,R.sub.3 is a saturated or unsaturated hydrocarbon radical,R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, alkyl, alkoxy or aryloxy, andX is a direct single bond or a methylene or ethylene bridge.These compounds are especially suitable for the preparation of photoresist compositions which can be used both for the production of positive as well as negative images. The photoresists are preferably used for deep-UV microlithography.

    摘要翻译： 含有至少一个带有一个或多个一个或多个式I的四氢吡喃氧基取代基的芳族环系的非聚合化合物其中R1是氢，卤素，烷基，环烷基，芳基，烷氧基或芳氧基，R2是氢 烷基，环烷基或芳基，R 3为饱和或不饱和烃基，R 4和R 5各自独立地为氢，卤素，烷基，烷氧基或芳氧基，X为直接单键或亚甲基或乙烯桥。 这些化合物特别适用于光刻胶组合物的制备，该组合物既可用于生产正面和负面图像。 光致抗蚀剂优选用于深UV微光刻。

    Acid labile solution inhibitors and positive- and negative-acting photosensitive composition based thereon
    2.
    发明授权
    Acid labile solution inhibitors and positive- and negative-acting photosensitive composition based thereon 失效
    酸不稳定溶液抑制剂和基于其的正性和负性感光性组合物

    公开(公告)号：US5380881A

    公开(公告)日：1995-01-10

    申请号：US7420

    申请日：1993-01-22

    申请人： Ulrich Schadeli

    发明人： Ulrich Schadeli

    IPC分类号： C07D309/10 ,  G03C1/73 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

    CPC分类号： C07D309/10 ,  G03F7/0045 ,  Y10S430/106

    摘要： Non-polymeric compounds which contain at least one aromatic ring system carrying one or more one or more tetrahydropyranyloxy substituents of formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl, cycloalkyl, aryl, alkoxy or aryloxy,R.sub.2 is hydrogen, alkyl, cycloalkyl or aryl,R.sub.3 is a saturated or unsaturated hydrocarbon radical,R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, alkyl, alkoxy or aryloxy, andX is a direct single bond or a methylene or ethylene bridge.These compounds are especially suitable for the preparation of photoresist compositions which can be used both for the production of positive as well as negative images. The photoresists are preferably used for deep-UV microlithography.

    摘要翻译： 含有至少一个带有一个或多个一个或多个式I的四氢吡喃氧基取代基的芳族环系的非聚合化合物其中R1是氢，卤素，烷基，环烷基，芳基，烷氧基或芳氧基，R2是氢 烷基，环烷基或芳基，R 3为饱和或不饱和烃基，R 4和R 5各自独立地为氢，卤素，烷基，烷氧基或芳氧基，X为直接单键或亚甲基或乙烯桥。 这些化合物特别适用于光刻胶组合物的制备，该组合物既可用于生产正面和负面图像。 光致抗蚀剂优选用于深UV微光刻。

    Positive photoresist having improved processing properties
    3.
    发明授权
    Positive photoresist having improved processing properties 失效
    正光致抗蚀剂具有改进的加工性能

    公开(公告)号：US5369200A

    公开(公告)日：1994-11-29

    申请号：US160818

    申请日：1993-12-03

    申请人： Ulrich Schadeli ,  Norbert Munzel

    发明人： Ulrich Schadeli ,  Norbert Munzel

    IPC分类号： C08F12/22 ,  C08F12/00 ,  C08F22/36 ,  C08F22/40 ,  C08F222/40 ,  C08K5/20 ,  C08L25/00 ,  C08L25/18 ,  C08L33/04 ,  C08L33/24 ,  C08L35/00 ,  G03F7/004 ,  G03F7/039

    CPC分类号： G03F7/039 ,  C08F222/40

    摘要： Polymers having a molecular weight (weight average) M.sub.w from 10.sup.3 to 10.sup.6, comprising recurring structural units of the formulae (I), (IIa) and (IIb) ##STR1## in which R.sub.1 is hydrogen or methyl, Y is a direct bond or a divalent radical of the formula (III) ##STR2## in which Z is a C.sub.1 -C.sub.6 alkylene group bound to the phenyl nucleus,OR.sub.2 is an acid-cleavable radical,in which R.sub.2 is C.sub.4 -C.sub.10 tert-alkyl, allyl, cyclohex-2-enyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms, trialkylsilyl or a group of the formulae (IV)-(VII) ##STR3## in which R.sub.8 is C.sub.1 -C.sub.6 alkyl, or C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms,R.sub.3 and R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms,R.sub.5 and R.sub.6 independently of one another are hydrogen or methyl,X is C.sub.1 -C.sub.6 alkylene and R.sub.7 is C.sub.1 -C.sub.6 alkyl, or C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms, or is --CO--R.sub.8 in which R.sub.8 is as defined in formula (IV), are suitable for use in DUV positive photoresists which show greatly reduced delay time effects and are distinguished by a high thermal stability and high resolution capacity.

    摘要翻译： 具有式（I），（IIa）和（IIb）的重复结构单元的分子量（重均分子量）Mw为103〜106的聚合物（IIa）（IIb）（IIb） ）其中R 1是氢或甲基，Y是直接键或式（III）的二价基团其中Z是与苯基结合的C 1 -C 6亚烷基，OR 2是酸 - C 1 -C 6烷基，C 1 -C 6烷氧基或卤素取代的未取代或单取代或多取代的C 1 -C 10烷基，烯丙基，环己-2-烯基，C 6 -C 14芳基或C 7 -C 16芳烷基 （VI）其中R 8为C 1 -C 6烷基或C 6 -C 6烷基的化合物（Ⅶ）（Ⅶ） C1-C6烷基，C1-C6烷氧基或卤素原子未取代或单取代或多取代的-C14芳基或C7-C16芳烷基，R3和R4彼此独立地是氢，C1-C6烷基，C1-C6烷氧基或 卤素原子，R5和R6独立地表示 另一个是氢或甲基，X是C1-C6亚烷基，R7是C1-C6烷基或C6-C14芳基或C7-C16芳烷基，它们是未取代的或被C1-C6烷基，C1-C6烷氧基或卤素单取代或多取代 或者是其中R8如式（IV）中所定义的-CO-R8，适用于DUV正性光致抗蚀剂，其显示出大大降低的延迟时间效应，并被高热稳定性和高分辨能力区分。

    Wet-chemical, developable, etch-stable photoresist for UV radiation with a wavelength below 200 nm
    6.
    发明授权
    Wet-chemical, developable, etch-stable photoresist for UV radiation with a wavelength below 200 nm 失效
    湿化学，可显影，蚀刻稳定的光致抗蚀剂，其波长低于200nm

    公开(公告)号：US6063549A

    公开(公告)日：2000-05-16

    申请号：US86006

    申请日：1998-05-27

    申请人： Ulrich Schadeli ,  Manfred Hofmann ,  Norbert Muenzel ,  Arnold Grubenmann

    发明人： Ulrich Schadeli ,  Manfred Hofmann ,  Norbert Muenzel ,  Arnold Grubenmann

    IPC分类号： G03F7/004 ,  G03F7/023 ,  G03F7/029 ,  G03F7/033 ,  G03F7/038 ,  G03F7/039 ,  G03F7/40 ,  H01L21/027

    CPC分类号： G03F7/039 ,  G03F7/0045 ,  G03F7/40

    摘要： Photoresist compositions are described, which are sufficiently transparent in the solvent-free state for radiation of a wavelength of approximately 193 nm, and which contain nonaromatic chemical groups, which can be converted into groups with aromatic structural elements (latent aromatic groups) under process conditions, for which an image structure comprised of the resist material is not disrupted. A preferred component with latent aromatic groups is bicyclo[3.2.2]nona-6,8-dien-3-one. Resist coatings, which are produced with these compositions, show a stability in plasma etching, which is comparable with the stability of conventional resists based on phenolic resins.

    摘要翻译： 描述了光致抗蚀剂组合物，其在无溶剂状态下对于约193nm的波长的辐射是足够透明的，并且其含有非芳族化学基团，其可以在加工条件下转化成具有芳族结构元素（潜芳族基团）的基团 由抗蚀剂材料构成的图像结构不被破坏。 具有潜芳族基团的优选组分是双环[3.2.2]壬-6,8-二烯-3-酮。 用这些组合物生产的抗蚀涂层表现出等离子体蚀刻中的稳定性，其与基于酚醛树脂的常规抗蚀剂的稳定性相当。

    Copolymers crosslinkable by acid catalysis
    8.
    发明授权
    Copolymers crosslinkable by acid catalysis 失效
    通过酸催化可交联的共聚物

    公开(公告)号：US5274060A

    公开(公告)日：1993-12-28

    申请号：US843798

    申请日：1992-02-27

    申请人： Ulrich Schadeli

    发明人： Ulrich Schadeli

    IPC分类号： C08F8/00 ,  C08F12/00 ,  C08F20/52 ,  C08F22/40 ,  C08F212/14 ,  G03F7/038 ,  H01L21/027 ,  H05K3/06 ,  C08F224/00 ,  C08F216/38

    CPC分类号： G03F7/038 ,  C08F212/14

    摘要： Copolymers having a molecular weight (Mw) of from 10.sup.3 to 10.sup.6, measured by gel-permeation chromatography, that are crosslinkable by acid catalysis and that consist ofa) 100-80 mol. % of structural repeating units of formulae I and II ##STR1## in a ratio of from 1:1 to 1:9 and b) 0-20 mol. % of structural repeating units of formula III ##STR2## wherein X and X' each independently of the other are ##STR3## R is hydrogen or a protecting group that can be removed by the action of acids, the radicals R.sub.1 each independently of the other are C.sub.1 -C.sub.5 alkyl, phenyl or naphthyl or together are 1,2-phenylene or --[C(R.sub.3)(R.sub.4)].sub.x -- wherein R.sub.3 and/or R.sub.4 =hydrogen or methyl and x is from 2 to 5, the radicals R.sub.2 each independently of the other are hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, R.sub.5 and R.sub.7 are each hydrogen, R.sub.6 is hydrogen, halogen or methyl and R.sub.8 is hydrogen, halogen, methyl, --CH.sub.2 halogen, --CH.sub.2 CN, --CN, --COOH, --CONH.sub.2, --O--C.sub.1 -C.sub.5 alkyl, --O--CO--C.sub.1 -C.sub.5 alkyl, --COO--C.sub.1 -C.sub.5 alkyl, --COO-phenyl or phenyl, or R.sub.5 and R.sub.6 are each hydrogen and R.sub.7 and R.sub.8 together are --CO--O--CO-- or each independently of the other are --COOH or --COO--C.sub.1 -C.sub.5 alkyl, are described.The said copolymers are suitable, together with compounds that form an acid under actinic radiation, for the production of negative resist systems.

    摘要翻译： 通过凝胶渗透色谱法测定的分子量（Mw）为103至106的共聚物，其可通过酸催化交联并且由以下组成：a）100-80mol。 式I和II的结构重复单元的比例为1：1至1：9，b）为0-20摩尔。 式III的结构重复单元的％（III）其中X和X'各自独立地是氢或可以通过酸的作用除去的保护基，基团R1各自独立地 的另一个是C 1 -C 5烷基，苯基或萘基或一起是1,2-亚苯基或 - [C（R 3）（R 4）] x - ，其中R 3和/或R 4 =氢或甲基，x为2至5， 基团R 2各自独立地为氢，C 1 -C 5烷基或C 1 -C 5烷氧基，R 5和R 7各自为氢，R 6为氢，卤素或甲基，R 8为氢，卤素，甲基，-CH 2卤素，-CH 2 CN，-CN ，-COOH，-CONH 2，-O-C 1 -C 5烷基，-O-CO-C 1 -C 5烷基，-COO-C 1 -C 5烷基，-COO-苯基或苯基，或R 5和R 6各自为氢，并且R 7和R 8一起为 -CO-O-CO-或各自独立地为-COOH或-COO-C 1 -C 5烷基。 所述共聚物与在光化辐射下形成酸的化合物一起适用于制备负性抗蚀剂体系。

    Positive photoresist having improved processing properties
    10.
    发明授权
    Positive photoresist having improved processing properties 失效
    正光致抗蚀剂具有改进的加工性能

    公开(公告)号：US5397680A

    公开(公告)日：1995-03-14

    申请号：US249972

    申请日：1994-05-27

    申请人： Ulrich Schadeli ,  Norbert Munzel

    发明人： Ulrich Schadeli ,  Norbert Munzel

    IPC分类号： C08F12/22 ,  C08F12/00 ,  C08F22/36 ,  C08F22/40 ,  C08F222/40 ,  C08K5/20 ,  C08L25/00 ,  C08L25/18 ,  C08L33/04 ,  C08L33/24 ,  C08L35/00 ,  G03F7/004 ,  G03F7/039 ,  G03C1/73

    CPC分类号： G03F7/039 ,  C08F222/40

    摘要： Polymers having a molecular weight (weight average) M.sub.w from 10.sup.3 to 10.sup.6, comprising recurring structural units of the formulae (I), (IIa) and (IIb) ##STR1## in which R.sub.1 is hydrogen or methyl, Y is a direct bond or a divalent radical of the formula (III) ##STR2## in which Z is a C.sub.1 -C.sub.6 alkylene group bound to the phenyl nucleus,OR.sub.2 is an acid-cleavable radical,in which R.sub.2 is C.sub.4 -C.sub.10 tert-alkyl, allyl, cyclohex-2-enyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms, trialkylsilyl or a group of the formulae (IV)-(VII) ##STR3## in which R.sub.8 is C.sub.1 -C.sub.6 alkyl, or C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms,R.sub.3 and R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms,R.sub.5 and R.sub.6 independently of one another are hydrogen or methyl,X is C.sub.1 -C.sub.6 alkylene and R.sub.7 is C.sub.1 -C.sub.6 alkyl, or C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.16 aralkyl which are unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms, or is --CO--R.sub.8 in which R.sub.8 is as defined in formula (IV),are suitable for use in DUV positive photoresists which show greatly reduced delay time effects and are distinguished by a high thermal stability and high resolution capacity.

    摘要翻译： 具有式（I），（IIa）和（IIb）的重复结构单元的分子量（重均分子量）Mw为103〜106的聚合物（IIa）（IIb）（IIb） ）其中R 1是氢或甲基，Y是直接键或式（III）的二价基团其中Z是与苯基结合的C 1 -C 6亚烷基，OR 2是酸 - C 1 -C 6烷基，C 1 -C 6烷氧基或卤素取代的未取代或单取代或多取代的C 1 -C 10烷基，烯丙基，环己-2-烯基，C 6 -C 14芳基或C 7 -C 16芳烷基 （VI）其中R 8为C 1 -C 6烷基或C 6 -C 6烷基的化合物（Ⅶ）（Ⅶ） C1-C6烷基，C1-C6烷氧基或卤素原子未取代或单取代或多取代的-C14芳基或C7-C16芳烷基，R3和R4彼此独立地是氢，C1-C6烷基，C1-C6烷氧基或 卤素原子，R5和R6独立地表示 另一个是氢或甲基，X是C1-C6亚烷基，R7是C1-C6烷基或C6-C14芳基或C7-C16芳烷基，它们是未取代的或被C1-C6烷基，C1-C6烷氧基或卤素单取代或多取代 或者是其中R8如式（IV）中所定义的-CO-R8，适用于DUV正性光致抗蚀剂，其显示出大大降低的延迟时间效应，并被高热稳定性和高分辨能力区分。