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1. 发明授权

US5132376A Process for selective removal of dimeric species from phenolic polymers 失效
标题翻译：从酚类聚合物中选择性去除二聚物质的方法
公开(公告)号：US5132376A
公开(公告)日：1992-07-21
申请号：US630673
申请日：1990-12-20
申请人： Thomas R. Sarubbi
发明人： Thomas R. Sarubbi
IPC分类号： C08G8/08 , C08G8/28 , G03F7/023
CPC分类号： C08G8/08 , C08G8/28 , G03F7/023 , G03F7/0236
摘要： Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.
摘要翻译：用于生产无二聚体酚醛聚合物，特别是由甲酚混合物制备的酚醛清漆聚合物的方法，以及含有这种无二聚体的酚醛清漆聚合物的光致抗蚀剂组合物。该方法包括使含有酚二聚体的酚醛聚合物与封端剂如甲硅烷基化试剂反应以封闭所有酚羟基。这降低了封端二聚体的蒸馏温度，并使封端聚合物在这样的蒸馏温度下稳定。将封端的二聚体蒸馏出去，最后酚类聚合物不起泡。无二聚体酚醛清漆产生无浮渣的显影光刻胶图像。

2. 发明授权

US5494785A High ortho-ortho bonded novolak binder resins and their use in a process for forming positive resist patterns 失效
标题翻译：高正离子键合酚醛清漆粘合剂树脂及其在形成正性抗蚀剂图案的方法中的用途
公开(公告)号：US5494785A
公开(公告)日：1996-02-27
申请号：US373685
申请日：1995-01-17
申请人： Joseph J. Sizensky , Thomas R. Sarubbi , Medhat A. Toukhy
发明人： Joseph J. Sizensky , Thomas R. Sarubbi , Medhat A. Toukhy
IPC分类号： C08G8/10 , C08G8/00 , C08G8/04 , C08L61/04 , C08L61/06 , G03F7/023 , G03F7/021 , C08F283/00
CPC分类号： C08G8/04 , G03F7/0236
摘要： A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C. to form a phenolic novolak having a weight average molecular weight of 3,000 to 40,000, having ortho-ortho bonding of between 50% and 70% of the methylene bonds between the phenolic moieties, and having a time to clear of at least 20 seconds per micron; wherein the mole ratio of said second aldehyde source to said total phenolic moieties is less than about 0.8:1.0.
摘要翻译：通过包括以下步骤的方法制备的酚醛清漆组合物：（1）在不存在催化剂的情况下，在大约100℃的反应温度下将包含至少一种三官能酚单体的主要部分的第一酚单体与第一醛源反应约200℃，反应压力为约2至约15个大气压，以形成重均分子量为约500至约2,000的酚低聚物，其邻位键合为约55％至约酚部分之间的75％的亚甲基键; 并有时间清除小于125秒每微米; 其中所述第一醛源与所述第一酚单体的摩尔比为约0.3:1.0至约0.55:1.0; 然后在约80℃至约150℃的温度下使所述低聚物与任选的第二酚源和第二醛源反应，形成重均分子量为3,000至40,000的酚醛清漆，具有在酚部分之间的50％和70％之间的亚甲基键的邻位键合，并且具有每微孔清除至少20秒的时间; 其中所述第二醛源与所述总酚部分的摩尔比小于约0.8:1.0。

3. 发明授权

US5473045A High ortho-ortho bonded novolak binder resins and their use in radiation-sensitive compositions 失效
标题翻译：高邻苯基酚醛清漆粘合剂树脂及其在辐射敏感组合物中的应用
公开(公告)号：US5473045A
公开(公告)日：1995-12-05
申请号：US373705
申请日：1995-01-17
申请人： Joseph J. Sizensky , Thomas R. Sarubbi , Medhat A. Toukhy
发明人： Joseph J. Sizensky , Thomas R. Sarubbi , Medhat A. Toukhy
IPC分类号： C08G8/10 , C08G8/00 , C08G8/04 , C08L61/04 , C08L61/06 , G03F7/023 , C08G14/04
CPC分类号： C08G8/04 , G03F7/0236
摘要： A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho--ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C. to form a phenolic novolak having a weight average molecular weight of 3,000 to 40,000, having ortho--ortho bonding of between 50% and 70% of the methylene bonds between the phenolic moieties, and having a time to clear of at least 20 seconds per micron; wherein the mole ratio of said second aldehyde source to said total phenolic moieties is less than about 0.8:1.0.
摘要翻译：通过包括以下步骤的方法制备的酚醛清漆组合物：（1）在不存在催化剂的情况下，在大约100℃的反应温度下将包含至少一种三官能酚单体的主要部分的第一酚单体与第一醛源反应约200℃，反应压力为约2至约15个大气压，以形成重均分子量为约500至约2,000的酚低聚物，其邻位键合为约55％至约酚部分之间的75％的亚甲基键; 并有时间清除小于125秒每微米; 其中所述第一醛源与所述第一酚单体的摩尔比为约0.3:1.0至约0.55:1.0; 然后在约80℃至约150℃的温度下使所述低聚物与任选的第二酚源和第二醛源反应，形成重均分子量为3,000至40,000的酚醛清漆，具有在酚部分之间的50％和70％之间的亚甲基键的邻位键合，并且具有每微孔清除至少20秒的时间; 其中所述第二醛源与所述总酚部分的摩尔比小于约0.8:1.0。

4. 发明授权

US5338652A Selected structurally defined novolak binder resins and their use in photoresist pattern formation 失效
标题翻译：选择结构定义的酚醛清漆粘合剂树脂及其在光致抗蚀剂图案形成中的用途
公开(公告)号：US5338652A
公开(公告)日：1994-08-16
申请号：US194293
申请日：1994-02-09
申请人： Thomas R. Sarubbi , Joseph J. Sizensky
发明人： Thomas R. Sarubbi , Joseph J. Sizensky
IPC分类号： C08G8/08 , G03F7/023 , G03F7/30
CPC分类号： G03F7/0236 , C08G8/08
摘要： A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms; whereinR.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; and whereinX is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S; with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; and whereinR.sub.4 is selected from H and CH.sub.3.
摘要翻译：一种酚醛清漆树脂组合物，其包含至少一个具有式（A）的对位，对位键合双酚的反应产物单元：其中R1 =氢，具有1-4个碳原子的低级烷基，卤素，或具有1-4个碳原子的低级烷氧基; 其中R2 =氢或具有1-4个碳原子的低级烷基; 并且其中X选自：CH 2，CH（CH 3），C（CH 3）2，O和S; 与选自式（B）的双官能邻位，邻苯二酚双羟甲基的双羟甲基单体，由式（C）表示的双官能邻位，对 - 酚双羟甲基：由CH3，CH2CH3，Cl和Br取代; 并且其中R 4选自H和CH 3。

5. 发明授权

US4837121A Thermally stable light-sensitive compositions with o-quinone diazide and phenolic resin 失效
标题翻译：具有邻醌二叠氮和酚醛树脂的热稳定的光敏组合物
公开(公告)号：US4837121A
公开(公告)日：1989-06-06
申请号：US124227
申请日：1987-11-23
申请人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
发明人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
IPC分类号： C08G8/00 , C08G8/14 , C08G8/20 , C08G8/22 , C08G8/24 , C08G65/38 , C08L61/04 , C08L61/14 , C09D161/04 , C09D161/14 , G03F7/023 , H01L21/027 , H01L21/30
CPC分类号： G03F7/0236 , C08G8/24
摘要： A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers ) to prepare a light-sensitive composition useful as a positive-working photoresist.
摘要翻译：一种包含式（I）单元的酚醛树脂组合物：其中R1是卤素，R2是具有1-4个碳原子的低级烷基，并且所述式（I）单元是通过将相应的式（A）的卤素取代的间苯二酚：其中R 1如上定义，与式（B）的相应的对位低级烷基取代的2,6-双（羟甲基） - 苯酚：（B）其中R2定义如上，其中A：B的摩尔比为约0.5:1至1.7:1。该酚醛树脂可以与光活性化合物（例如1,2-萘醌二叠氮化物增感剂）混合，以制备用作正性光致抗蚀剂的感光组合物。

6. 发明授权

US5350827A Selected structurally defined novolak binder resins and their use in radiation-sensitive compositions 失效
标题翻译：选定的结构定义的酚醛清漆粘合剂树脂及其在辐射敏感组合物中的用途
公开(公告)号：US5350827A
公开(公告)日：1994-09-27
申请号：US194292
申请日：1994-02-09
申请人： Thomas R. Sarubbi , Joseph J. Sizensky
发明人： Thomas R. Sarubbi , Joseph J. Sizensky
IPC分类号： C08G8/08 , G03F7/023 , C08G8/04 , C08G8/10
CPC分类号： G03F7/0236 , C08G8/08
摘要： A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms;wherein R.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; andwherein X is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S;with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; andwherein R.sub.4 is selected from H and CH.sub.3.
摘要翻译：一种酚醛清漆树脂组合物，其包含至少一个具有式（A）的对位，对位键合双酚的反应产物单元：其中R1 =氢，具有1-4个碳原子的低级烷基，卤素，或具有1-4个碳原子的低级烷氧基; 其中R2 =氢或具有1-4个碳原子的低级烷基; 并且其中X选自：CH 2，CH（CH 3），C（CH 3）2，O和S; 具有选自式（B）的双官能邻位，酚羟基羟乙基的双羟甲基单体，式（C）的双官能邻 - 对 - 酚双羟甲基：由CH 3，CH 2 CH 3，Cl和Br取代; 并且其中R 4选自H和CH 3。

7. 发明授权

US5151339A Photoresist composition containing diazoquinone photosensitizer and novalak resin characterized by the complete and selective removal of dimeric species from the novolak resin 失效
标题翻译：含有重氮醌光敏剂和诺瓦克树脂的光致抗蚀剂组合物，其特征在于从酚醛清漆树脂中完全和选择性地除去二聚物质
公开(公告)号：US5151339A
公开(公告)日：1992-09-29
申请号：US702155
申请日：1991-05-15
申请人： Thomas R. Sarubbi
发明人： Thomas R. Sarubbi
IPC分类号： C08G8/08 , C08G8/28 , G03F7/023
CPC分类号： G03F7/0236 , C08G8/08 , C08G8/28 , G03F7/023
摘要： Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.
摘要翻译：用于生产无二聚体酚醛聚合物，特别是由甲酚混合物制备的酚醛清漆聚合物的方法，以及含有这种无二聚体的酚醛清漆聚合物的光致抗蚀剂组合物。该方法包括使含有酚二聚体的酚醛聚合物与封端剂如甲硅烷基化试剂反应以封闭所有酚羟基。这降低了封端二聚体的蒸馏温度，并使封端聚合物在这样的蒸馏温度下稳定。将封端的二聚体蒸馏出去，最后酚类聚合物不起泡。无二聚体酚醛清漆产生无浮渣的显影光刻胶图像。

8. 发明授权

US4970287A Thermally stable phenolic resin compositions with ortho, ortho methylene linkage 失效
标题翻译：具有邻位，邻亚甲基键的热稳定性酚醛树脂组合物
公开(公告)号：US4970287A
公开(公告)日：1990-11-13
申请号：US325399
申请日：1989-03-20
申请人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
发明人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
IPC分类号： C08G8/24 , G03F7/023
CPC分类号： C08G8/24 , G03F7/0236
摘要： A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms, and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers) to prepare a light-sensitive composition useful as a positive-working photoresist.
摘要翻译：一种包含式（I）单元的酚醛树脂组合物：其中R 1是卤素，R 2是具有1至4个碳原子的低级烷基，式（I）的单元是通过将相应的式（A）的卤素取代的间苯二酚：其中R 1如上定义，与式（B）的相应的对位低级烷基取代的2,6-双（羟甲基） - 苯酚：（B）其中R2定义如上，其中A:B的摩尔比为约0.5:1至1.7:1。该酚醛树脂可以与光活性化合物（例如1,2-萘醌二叠氮化物增感剂）混合，以制备用作正性光致抗蚀剂的感光组合物。

9. 发明授权

US5024921A Thermally stable light-sensitive compositions with o-quinone diazide and phenolic resin used in a method of forming a positive photoresist image 失效
标题翻译：在形成正性光致抗蚀剂图像的方法中使用的具有邻醌二叠氮化物和酚醛树脂的热稳定的光敏组合物
公开(公告)号：US5024921A
公开(公告)日：1991-06-18
申请号：US552394
申请日：1990-09-21
申请人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
发明人： Andrew J. Blakeney , Alfred T. Jeffries, III , Thomas R. Sarubbi
IPC分类号： C08G8/24 , G03F7/023
CPC分类号： G03F7/0236 , C08G8/24
摘要： A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-napthoquinone diazide sensitizers) to prepare a light-sensitive composition useful in a method for forming a positive photoresist image.
摘要翻译：一种包含式（I）单元的酚醛树脂组合物：其中R1是卤素，R2是具有1-4个碳原子的低级烷基，式（I）的单元是通过将相应的式（A）的卤素取代的间苯二酚：其中R 1如上定义，与式（B）的相应的对位低级烷基取代的2,6-双（羟甲基） - 苯酚：（B）其中R2定义如上，其中A：B的摩尔比为约0.5:1至1.7:1。该酚醛树脂可以与光活性化合物（例如1,2-萘醌二叠氮化物增感剂）混合，以制备用于形成正性光致抗蚀剂图像的方法中的感光组合物。

10. 发明申请

US20080199814A1 Device manufacturing process utilizing a double patterning process 审中-公开
标题翻译：利用双重图案化工艺的器件制造工艺
公开(公告)号：US20080199814A1
公开(公告)日：2008-08-21
申请号：US11999104
申请日：2007-12-04
申请人： Dave Brzozowy , Thomas R. Sarubbi , Sanjay Malik , Gregory Spaziano
发明人： Dave Brzozowy , Thomas R. Sarubbi , Sanjay Malik , Gregory Spaziano
IPC分类号： H01L21/00
CPC分类号： G03F7/0035 , G03F7/095
摘要： Manufacturing semiconductor device by steps of: a) providing substrate with antireflective coating or underlayer, b) applying first photosensitive composition over substrate, c) exposing first composition to radiation to produce first pattern, d) developing exposed first composition to produce an imaged bilayer stack, e) rinsing the stack, f) applying fixer to the stack, g) applying optional bake, h) rinsing the stack, i) applying second optional bake, j) applying second photosensitive composition onto the stack to produce multilayer stack, k) exposing second composition to produce second pattern offset from first pattern, l) developing exposed second composition to produce multilayer stack, and m) rinsing multilayer stack; the photosensitive compositions have photoacid generator and substantially aqueous base insoluble polymer whose solubility increases upon treatment with acid and further comprises an anchor group, and the fixer is a polyfunctional compound reactive with anchor group, but does not contain silicon and the substrate stays within a lithographic cell from at least first coating step until at least after final exposure.
摘要翻译：通过以下步骤制造半导体器件：a）向衬底提供抗反射涂层或底层，b）在衬底上施加第一感光组合物，c）将第一组合物暴露于辐射以产生第一图案，d）显影暴露的第一组合物以产生成像双层叠层 e）冲洗堆叠，f）将定影剂施加到堆叠，g）施加任选的烘烤，h）冲洗该堆叠，i）施加第二可选烘烤，j）将第二光敏组合物施加到堆叠上以产生多层堆叠，k）暴露第二组合物以产生从第一图案偏移的第二图案，l）显影暴露的第二组合物以产生多层堆叠，以及m）漂洗多层堆叠; 光敏组合物具有光酸产生剂和基本上不溶于碱的水溶性聚合物，其在用酸处理时溶解度增加，并且还包含锚定基团，并且定影剂是与锚定基团反应但不含硅的多官能化合物，并且底物保留在光刻至少在第一次涂覆步骤至少在最终曝光后。

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