公开(公告)号：US5759740A

公开(公告)日：1998-06-02

申请号：US748298

申请日：1996-11-13

申请人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth ,  Stephan Ilg

发明人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth ,  Stephan Ilg

IPC分类号： C07D333/24 ,  C07C309/28 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0045 ,  Y10S430/11 ,  Y10S430/111 ,  Y10S430/12 ,  Y10S430/122 ,  Y10S430/123

摘要： The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituent; R.sub.0 is either a R.sub.1 -X group or R.sub.2 ; X is an oxygen or a sulfur atom; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, and R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or an acid-degradable substituent, as radiation-sensitive photoacid generator in a chemically amplified photoresist which is developable in alkaline medium and is sensitive to radiation of a wavelength in the range from 340-390 nm, and to corresponding positive-working and negative-working photoresists for the cited wavelength range.

摘要翻译： 本发明涉及式1的肟磺酸盐，其中R是萘基，Ar是未取代的芳基或芳基，其携带一个或多于一个选自以下的取代基： 硝基，氯，溴，羟基，C 1 -C 4烷基，C 1 -C 4全氟烷基，C 1 -C 4烷氧基和酸可降解取代基; R0是R1-X基团或R2; X是氧或硫原子; R 1是氢，C 1 -C 4烷基或未取代的苯基或被选自氯，溴，C 1 -C 4烷基和C 1 -C 4烷氧基的成员所取代的苯基，R 2是氢，C 1 -C 4烷基或酸可降解取代基 作为在碱性介质中可显影并对波长在340-390nm范围内的辐射敏感的化学放大光致抗蚀剂中的辐射敏感光致酸产生剂，以及用于所述波长的相应的正性和负性光致抗蚀剂 范围。

公开(公告)号：US5627011A

公开(公告)日：1997-05-06

申请号：US440388

申请日：1995-05-12

申请人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth ,  Stephan Ilg

发明人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth ,  Stephan Ilg

IPC分类号： C07D333/24 ,  C07C309/28 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0045 ,  Y10S430/11 ,  Y10S430/111 ,  Y10S430/12 ,  Y10S430/122 ,  Y10S430/123

摘要： The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituents;R.sub.0 is either a R.sub.1 --X group or R.sub.2 ;X is an oxygen or a sulfur atom;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, andR.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or an acid-degradable substituent, as radiation-sensitive photoacid generator in a chemically amplified photoresist which is developable in alkaline medium and is sensitive to radiation of a wavelength in the range from 340-390 nm, and to corresponding positive-working and negative-working photoresists for the cited wavelength range.

摘要翻译： 本发明涉及式1的肟磺酸盐，其中R是萘基，Ar是未取代的芳基或芳基，其携带一个或多于一个选自以下的取代基： 硝基，氯，溴，羟基，C 1 -C 4烷基，C 1 -C 4全氟烷基，C 1 -C 4烷氧基和酸可降解取代基; R0是R1-X基团或R2; X是氧或硫原子; R 1是氢，C 1 -C 4烷基或未取代的苯基或被选自氯，溴，C 1 -C 4烷基和C 1 -C 4烷氧基的成员所取代的苯基，R 2是氢，C 1 -C 4烷基或酸可降解取代基 作为在碱性介质中可显影并对波长在340-390nm范围内的辐射敏感的化学放大光致抗蚀剂中的辐射敏感光致酸产生剂，以及用于所述波长的相应的正性和负性光致抗蚀剂 范围。

公开(公告)号：US5650262A

公开(公告)日：1997-07-22

申请号：US417119

申请日：1995-04-05

申请人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth

发明人： Norbert Munzel ,  Reinhard Schulz ,  Heinz Holzwarth

IPC分类号： C07C39/04 ,  G03F7/004 ,  G03F7/038 ,  H01L21/027

CPC分类号： G03F7/038 ,  G03F7/0045 ,  G03F7/0382 ,  Y10S430/106 ,  Y10S430/122

摘要： The invention relates to a chemically amplified negative photoresist which can be developed in aqueous alkaline media, which contains a radiation-sensitive acid generator and a compound which reduces the solubility of the resist in aqueous alkaline solutions in the presence of acid, and a polyhydroxyl compound of the formula I ##STR1## in which n is an integer between 2 and 6,R is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl, andZ is an n-valent radical which is unsubstituted or substituted by one or more substituents from the group consisting of hydroxyl, halogen and C.sub.1 -C.sub.4 alkoxy, and is selected from the group consisting of:a) aliphatic radicals having 1 to 12 carbon atoms,b) cycloaliphatic radicals having 5 to 20 carbon atoms,c) aromatic radicals having 6 to 20 carbon atoms andd) radicals having 7 to 30 carbon atoms which comprise at least two different structural units selected from aliphatic, cycloaliphatic or aromatic groups. The resists described make it possible to reduce the demands made on the focusing accuracy during imagewise exposure.

摘要翻译： 本发明涉及一种可在含水碱性介质中显影的化学放大型负性光致抗蚀剂，其含有辐射敏感性酸产生剂和在酸存在下降低抗蚀剂在碱性水溶液中的溶解度的化合物，以及多羟基化合物 其中n是2和6之间的整数，R是氢，卤素，C 1 -C 4烷氧基或C 1 -C 4烷基，Z是未被取代或被一个取代的n价基团的式I 或更多的选自羟基，卤素和C 1 -C 4烷氧基的取代基，并且选自：a）具有1至12个碳原子的脂族基团，b）具有5至20个碳原子的脂环族基团，c）芳族 具有6至20个碳原子的基团和d）具有7至30个碳原子的基团，其包含至少两个选自脂肪族，脂环族或芳族基团的不同结构单元。 所描述的抗蚀剂使得可以降低在成像曝光期间对聚焦精度的要求。

公开(公告)号：US5436098A

公开(公告)日：1995-07-25

申请号：US180180

申请日：1994-01-11

申请人： Reinhard Schulz ,  Norbert Munzel ,  Martin Roth ,  Wilhelm Knobloch

发明人： Reinhard Schulz ,  Norbert Munzel ,  Martin Roth ,  Wilhelm Knobloch

IPC分类号： G03F7/004 ,  C07C39/15 ,  C07C309/71 ,  C07C309/76 ,  C08K5/42 ,  C08L101/00 ,  G03F7/022 ,  H01L21/027 ,  H05K3/00 ,  G03F7/023

CPC分类号： C07C309/76 ,  C07C39/15 ,  G03F7/0226

摘要： Positive photoresist compositions comprising, in an organic solvent, at leasta) one alkali-soluble resin,b) one photosensitive quinone diazide,c) one aromatic hydroxy compound of formula I ##STR1## wherein each R is --H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --OCH.sub.2 C.sub.6 H.sub.5, --OC.sub.6 H.sub.5 or --COOC.sub.1 -C.sub.4 alkyl, and R.sub.1 and R.sub.2 are each independently of the other H, C.sub.1 -C.sub.4 alkyl, --C.sub.6 H.sub.5 or a cycloaliphatic 5- or 6-membered ring, a is an integer from 0 to 4, and m and n are each independently of the other 0, 1 or 2, which compound enhances the photosensitivity and/or the rate of development, and optionallyd) additional customary modifiers, are eminently suitable for making relief structures.

摘要翻译： 正性光致抗蚀剂组合物，其在有机溶剂中包含至少一种碱溶性树脂，b）一种光敏醌二叠氮化物，c）一种式I的芳族羟基化合物，其中每个R是-H，C1 C 1-4烷基，C 1 -C 4烷氧基，-OCH 2 C 6 H 5，-OC 6 H 5或-COOC 1 -C 4烷基，R 1和R 2各自独立地为H，C 1 -C 4烷基，-C 6 H 5或脂环族五元或六元环，a为 0至4的整数，m和n各自独立地为0,1或2，该化合物增强了光敏性和/或显影速率，并且任选地d）另外的常规改性剂特别适用于制备浮雕结构 。

公开(公告)号：US5296330A

公开(公告)日：1994-03-22

申请号：US932128

申请日：1992-08-15

申请人： Reinhard Schulz ,  Norbert Munzel ,  Martin Roth ,  Wilhelm Knobloch

发明人： Reinhard Schulz ,  Norbert Munzel ,  Martin Roth ,  Wilhelm Knobloch

IPC分类号： G03F7/004 ,  C07C39/15 ,  C07C309/71 ,  C07C309/76 ,  C08K5/42 ,  C08L101/00 ,  G03F7/022 ,  H01L21/027 ,  H05K3/00 ,  G03F7/023 ,  G03C1/61

CPC分类号： C07C309/76 ,  C07C39/15 ,  G03F7/0226

摘要： Positive photoresist compositions comprising, in an organic solvent, at leasta) one alkali-soluble resin,b) one photosensitive quinone diazide,c) one aromatic hydroxy compound of formula I ##STR1## wherein each R is --H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --OCH.sub.2 C.sub.6 H.sub.5, --OC.sub.6 H.sub.5 or --COOC.sub.1 -C.sub.4 alkyl, and R.sub.1 and R.sub.2 are each independently of the other H, C.sub.1 -C.sub.4 alkyl, --C.sub.6 H.sub.5 or a cycloaliphatic 5- or 6-membered ring, a is an integer from 0 to 4, and m and n are each independently of the other 0, 1 or 2, which compound enhances the photosensitivity and/or the rate of development, and optionallyd) additional customary modifiers,are eminently suitable for making relief structures.

摘要翻译： 正性光致抗蚀剂组合物，其在有机溶剂中包含至少一种碱溶性树脂，b）一种光敏醌二叠氮化物，c）一种式I的芳族羟基化合物（*化学结构*）（I），其中每个R是 - H，C 1 -C 4烷基，C 1 -C 4烷氧基，-OCH 2 C 6 H 5，-OC 6 H 5或-COOC 1 -C 4烷基，R 1和R 2各自独立地为H，C 1 -C 4烷基，-C 6 H 5或脂环族五元或六元环， a是0至4的整数，m和n各自独立地为0,1或2，该化合物增强光敏性和/或显影速率，以及任选地d）另外的常规改性剂，特别适用于 做救济结构。

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。

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。