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11. 发明授权

US06803168B1 Composition for anti-reflective coating or radiation absorbing coating and compounds used in the composition 有权
标题翻译：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。

12. 发明授权

US06737492B2 Radiation absorbing polymer, composition for radiation absorbing coating, radiation absorbing coating and application thereof as anti-reflective coating 有权
标题翻译：辐射吸收聚合物，用于辐射吸收涂层的组合物，辐射吸收涂层及其作为抗反射涂层的应用
公开(公告)号：US06737492B2
公开(公告)日：2004-05-18
申请号：US10229219
申请日：2002-08-27
申请人： Wen-Bing Kang , Munirathna Padmanaban , Hatsuyuki Tanaka , Ken Kimura , Takanori Kudo , Georg Pawlowski
发明人： Wen-Bing Kang , Munirathna Padmanaban , Hatsuyuki Tanaka , Ken Kimura , Takanori Kudo , Georg Pawlowski
IPC分类号： C08F11636
CPC分类号： C09D4/00 , C08F246/00 , G03F7/091 , C08F220/26 , C08F220/58 , C08F212/00
摘要： A radiation absorbing polymer having chemically bonded thereto a radiation absorbing dye, which has high absorption at a predetermined wavelength radiation, which shows good adhesion to a substrate and good thin film-forming, which has no dependence upon resists, which is soluble in a solvent for photoresists but becomes insoluble after being baked; a composition for radiation absorbing coating containing this polymer, and a radiation absorbing coating such as an anti-reflective coating formed from this composition are disclosed. The radiation absorbing polymer comprises a copolymer containing at least both a recurring unit composed of a monomer containing a keto group and a divalent group (preferably a methylene group) in its side chain and a recurring unit composed of a monomer containing an organic chromophore bonded directly or through a linkage group to the main chain. This radiation absorbing polymer is dissolved in a solvent such as alcohol, aromatic hydrocarbon, ketone, ester, etc., and the resulting solution is applied to a wafer and baked to form a radiation absorbing coating such as an anti-reflective coating. On this coating is coated, for example, a chemically amplified resist. This coated substrate is then exposed to deep UV rays and is developed to form a fine resist pattern excluding the influence of standing wave.
摘要翻译：一种辐射吸收聚合物，其化学键合有辐射吸收染料，该辐射吸收染料在预定波长辐射下具有高吸收性，其对基底具有良好的粘附性，并且与溶于溶剂的抗蚀剂无关的良好的薄膜形成用于光致抗蚀剂，但在烘烤后变得不溶; 公开了含有这种聚合物的辐射吸收涂层用组合物和由该组合物形成的抗反射涂层等吸收辐射涂层。辐射吸收聚合物包括共聚物，其至少包含由侧链中含有酮基和二价基团（优选亚甲基）的单体构成的重复单元，以及由含有直接键合的有机发色团的单体构成的重复单元或通过连接组到主链。将这种辐射吸收聚合物溶于醇，芳族烃，酮，酯等溶剂中，将所得溶液施加到晶片上并烘烤以形成抗辐射涂层等吸收辐射的涂层。在该涂层上涂覆例如化学放大抗蚀剂。然后将该涂覆的基材暴露于深紫外线，并显影以形成除了驻波的影响之外的精细抗蚀剂图案。

13. 发明授权

US06468718B1 Radiation absorbing polymer, composition for radiation absorbing coating, radiation absorbing coating and application thereof as anti-reflective coating 有权
标题翻译：辐射吸收聚合物，用于辐射吸收涂层的组合物，辐射吸收涂层及其作为抗反射涂层的应用
公开(公告)号：US06468718B1
公开(公告)日：2002-10-22
申请号：US09244358
申请日：1999-02-04
申请人： Wen-Bing Kang , Munirathna Padmanaban , Hatsuyuki Tanaka , Ken Kimura , Takanori Kudo , Georg Pawlowski
发明人： Wen-Bing Kang , Munirathna Padmanaban , Hatsuyuki Tanaka , Ken Kimura , Takanori Kudo , Georg Pawlowski
IPC分类号： G03C173
CPC分类号： C09D4/00 , C08F246/00 , G03F7/091 , C08F220/26 , C08F220/58 , C08F212/00
摘要： A radiation absorbing polymer having chemically bonded thereto a radiation absorbing dye, which has high absorption at a predetermined wavelength radiation, which shows good adhesion to a substrate and good thin film-forming, which has no dependence upon resists, which is soluble in a solvent for photoresists but becomes insoluble after being baked; a composition for radiation absorbing coating containing this polymer, and a radiation absorbing coating such as an anti-reflective coating formed from this composition are disclosed. The radiation absorbing polymer comprises a copolymer containing at least both a recurring unit composed of a monomer containing a keto group and a divalent group (preferably a methylene group) in its side chain and a recurring unit composed of a monomer containing an organic chromophore bonded directly or through a linkage group to the main chain. This radiation absorbing polymer is dissolved in a solvent such as alcohol, aromatic hydrocarbon, ketone, ester, etc., and the resulting solution is applied to a wafer and baked to form a radiation absorbing coating such as an anti-reflective coating. On this coating is coated, for example, a chemically amplified resist. This coated substrate is then exposed to deep UV rays and is developed to form a fine resist pattern excluding the influence of standing wave.
摘要翻译：一种辐射吸收聚合物，其化学键合有辐射吸收染料，该辐射吸收染料在预定波长辐射下具有高吸收性，其对基底具有良好的粘附性，并且与溶于溶剂的抗蚀剂无关的良好的薄膜形成用于光致抗蚀剂，但在烘烤后变得不溶; 公开了含有这种聚合物的辐射吸收涂层用组合物和由该组合物形成的抗反射涂层等吸收辐射涂层。辐射吸收聚合物包括共聚物，其至少包含由侧链中含有酮基和二价基团（优选亚甲基）的单体构成的重复单元，以及由含有直接键合的有机发色团的单体构成的重复单元或通过连接组到主链。将这种辐射吸收聚合物溶于醇，芳族烃，酮，酯等溶剂中，将所得溶液施加到晶片上并烘烤以形成抗辐射涂层等吸收辐射的涂层。在该涂层上涂覆例如化学放大抗蚀剂。然后将该涂覆的基材暴露于深紫外线，并显影以形成除了驻波的影响之外的精细抗蚀剂图案。

14. 发明授权

US06329117B1 Antireflection or light-absorbing coating composition and polymer therefor 有权
标题翻译：防反射或光吸收涂料组合物及其聚合物
公开(公告)号：US06329117B1
公开(公告)日：2001-12-11
申请号：US09319129
申请日：1999-08-09
申请人： Munirathna Padmanaban , Wen-Bing Kang , Georg Pawlowski , Ken Kimura , Hatsuyuki Tanaka
发明人： Munirathna Padmanaban , Wen-Bing Kang , Georg Pawlowski , Ken Kimura , Hatsuyuki Tanaka
IPC分类号： G03C173
CPC分类号： G03F7/091 , Y10S430/106 , Y10S430/107 , Y10S430/108 , Y10S430/111
摘要： A composition for an anti-reflective coating or a light absorbing coating, which shows good light absorption for lights of 100-450 nm in wavelength, suffers neither footing nor intermixing, and has excellent storage stability and step coverage, and novel copolymers to be used therein. The novel polymers comprise acrylic or methacrylic copolymers or terpolymers, at least having both recurring units (1) wherein an amino group- or hydroxyl-group containing organic chromophore capable of absorbing lights of 100 to 450 nm in wavelength is chemically bound to the carbonyl group bound to a carbon atom in the main chain, directly or through —R1NHCXY— (wherein R1 represents an alkylene group, X represents O or S, Y represents O or NR6, R6 represents H, a substituted or non-substituted, straight chain or cyclic alkyl group or a phenylene group) and for example recurring units (2) wherein a double bond-or epoxy group-containing alkyl group is chemically bound to the carboxyl or oxygen group bound to a carbon atom in the main chain. The composition containing the copolymer is coated on a wafer to form a bottom anti-reflective coating and, after coating thereon a photoresist, deep UV exposure and development are conducted to form a resist image with high resolution.
摘要翻译：用于抗反射涂层或光吸收涂层的组合物对于波长为100-450nm的光显示出良好的光吸收，既不起脚也不混合，并且具有优异的储存稳定性和阶梯覆盖率，以及要使用的新型共聚物其中。该新型聚合物包含至少具有两个重复单元（1）的丙烯酸或甲基丙烯酸共聚物或三元共聚物，其中能够吸收波长为100至450nm的光的含氨基或羟基的有机发色团与羰基化学键合直接或通过-R1NHCXY-（其中R1表示亚烷基，X表示O或S，Y表示O或NR6，R6表示H，取代或未取代的直链或未取代的直链或环状烷基或亚苯基），例如其中双键或含环氧基的烷基与与主链中的碳原子结合的羧基或氧基化学键合的重复单元（2）。将包含共聚物的组合物涂覆在晶片上以形成底部抗反射涂层，并且在其上涂覆光致抗蚀剂之后，进行深紫外线曝光和显影以形成具有高分辨率的抗蚀剂图像。

15. 发明授权

US06277750B1 Composition for bottom reflection preventive film and novel polymeric dye for use in the same 失效
标题翻译：用于底部防反射膜的组合物和用于其的新型聚合物染料
公开(公告)号：US06277750B1
公开(公告)日：2001-08-21
申请号：US09508624
申请日：2000-06-27
申请人： Georg Pawlowski , Munirathna Padmanaban , Wen-Bing Kang , Hatsuyuki Tanaka , Ken Kimura , Yoshinori Nishiwaki
发明人： Georg Pawlowski , Munirathna Padmanaban , Wen-Bing Kang , Hatsuyuki Tanaka , Ken Kimura , Yoshinori Nishiwaki
IPC分类号： H01L2100
CPC分类号： G03F7/091 , C08F8/28 , C08F2800/10 , G03F7/0382 , G03F7/0392 , C08F8/48 , C08F16/06
摘要： As a bottom anti-reflective coating material for use in photolithography, polymer dyes represented by following general formula are used. The polymer dyes are able to form a bottom anti-reflective coating having good film formation properties, good absorption properties at exposure wavelength, good step coverage, non-intermixing with photoresist and high etch rate. wherein R represents H or a substituted or non-substituted alkyl, cycloalkyl, or aryl group, R1 represents a substituted or non-substituted alkyl or aryl, or a —COOR3 group in which R3 represents an alkyl group, R2 represents a substituted or non-substituted alkyl, cycloalkyl, or aryl group, D is an organic chromophore which absorbs at the exposure wavelength (150-450 nm) and represents a substituted or non-substituted aryl, condensed aryl, or heteroaryl group, m and o are any integer above zero, and n, p and q are any integer including zero.
摘要翻译：作为用于光刻的底部抗反射涂层材料，使用由以下通式表示的聚合物染料。聚合物染料能够形成底部抗反射涂层，其具有良好的成膜性能，在曝光波长下具有良好的吸收性能，良好的步骤覆盖率，与光致抗蚀剂的非混合和高蚀刻速率。其中R表示H或取代或未取代的烷基，环烷基或芳基，R 1表示取代或未取代的烷基或芳基或其中R 3表示烷基的-COOR 3基团，R 2表示取代或未取代的烷基，环烷基或芳基，D 是在曝光波长（150-450nm）下吸收并表示取代或未取代的芳基，缩合芳基或杂芳基的有机发色团，m和o是大于零的任何整数，n，p和q是任何整数包括零。

16. 发明授权

US09298094B2 Composition for forming fine pattern and method for forming fined pattern using same 有权
标题翻译：用于形成精细图案的组合物和使用其形成精细图案的方法
公开(公告)号：US09298094B2
公开(公告)日：2016-03-29
申请号：US14127331
申请日：2012-07-13
申请人： Toshira Okamura , Georg Pawlowski , Masahiro Ishii
发明人： Toshira Okamura , Georg Pawlowski , Masahiro Ishii
IPC分类号： C08F226/02 , G03F7/32 , H01L21/027 , G03F7/40 , C09D139/00 , C08F226/04 , C08F8/28 , C08F8/30 , C08F8/34
CPC分类号： G03F7/32 , C08F8/28 , C08F8/30 , C08F8/34 , C08F226/02 , C08F226/04 , C08F2800/10 , C08F2810/30 , C08F2810/50 , C09D139/00 , G03F7/405 , H01L21/0273 , Y10T428/24802 , C08F126/02 , C08F8/12
摘要： The present invention provides a resist pattern-forming composition capable of forming a resist pattern excellent in etching resistance. The invention also provides a resist pattern formation method using that composition. The composition comprises pure water and a water-soluble resin having aromatic group-containing substituents in its side chain. The composition also contains a free acid or an acid group combined with the water-soluble resin.
摘要翻译：本发明提供能够形成抗蚀刻性优异的抗蚀剂图案的抗蚀剂图案形成组合物。本发明还提供了使用该组合物的抗蚀剂图案形成方法。该组合物包含纯水和其侧链中具有含芳基的取代基的水溶性树脂。该组合物还含有与水溶性树脂组合的游离酸或酸基。

17. 发明申请

US20060177774A1 Process of imaging a photoresist with multiple antireflective coatings 失效
标题翻译：用多个抗反射涂层成像光致抗蚀剂的工艺
公开(公告)号：US20060177774A1
公开(公告)日：2006-08-10
申请号：US11338462
申请日：2006-01-24
申请人： David Abdallah , Mark Neisser , Ralph Dammel , Georg Pawlowski , John Biafore , Andrew Romano , WooKyu Kim
发明人： David Abdallah , Mark Neisser , Ralph Dammel , Georg Pawlowski , John Biafore , Andrew Romano , WooKyu Kim
IPC分类号： G03C5/00
CPC分类号： G03F7/091 , Y10S430/151
摘要： A process for imaging a photoresist comprising the steps of, a) forming a stack of multiple layers of organic antireflective coatings on a substrate; b) forming a coating of a photoresist over the upper layer of the stack of multiple layers of organic antireflective coatings; c) imagewise exposing the photoresist with an exposure equipment; and, d) developing the coating with a developer.
摘要翻译：一种用于对光致抗蚀剂进行成像的方法，包括以下步骤：a）在衬底上形成多层有机抗反射涂层的叠层; b）在多层有机抗反射涂层的堆叠的上层上形成光致抗蚀剂的涂层; c）用曝光设备成像曝光光致抗蚀剂; 和d）用显影剂显影涂层。

18. 发明授权

US5442061A Radiation-sensitive sulfonic acid esters and their use 失效
标题翻译：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。

19. 发明授权

US5326826A Radiation-sensitive polymers containing diazocarbonyl groups and a process for their preparation 失效
标题翻译：含有重氮羰基的辐射敏感聚合物及其制备方法
公开(公告)号：US5326826A
公开(公告)日：1994-07-05
申请号：US841532
申请日：1992-02-26
申请人： Horst Roeschert , Hans-Joachim Merrem , Georg Pawlowski , Juergen Fuchs , Ralph Dammel
发明人： Horst Roeschert , Hans-Joachim Merrem , Georg Pawlowski , Juergen Fuchs , Ralph Dammel
IPC分类号： C08F8/30 , C08F12/00 , C08F12/14 , C08F212/14 , C08F220/20 , G03F7/039 , C03F7/023 , C08F30/08
CPC分类号： G03F7/039 , C08F8/30
摘要： Radiation-sensitive polymers, a mixture containing these radiation-sensitive polymers as binder, and a process for the preparation of the radiation-sensitive polymer binders are disclosed. A positive radiation-sensitive recording material containing the radiation-sensitive polymer is also disclosed.
摘要翻译：公开了辐射敏感聚合物，含有这些辐射敏感聚合物作为粘合剂的混合物，以及制备辐射敏感性聚合物粘合剂的方法。还公开了含有辐射敏感性聚合物的正性辐射敏感记录材料。

20. 发明授权

US5229254A Positive-working radiation-sensitive mixtures, and radiation-sensitive recording materials produced with these mixtures 失效
标题翻译：积极工作的辐射敏感性混合物，以及用这些混合物生产的辐射敏感记录材料
公开(公告)号：US5229254A
公开(公告)日：1993-07-20
申请号：US871027
申请日：1992-04-20
申请人： Gerhard Lohaus , Walter Spiess , Georg Pawlowski
发明人： Gerhard Lohaus , Walter Spiess , Georg Pawlowski
IPC分类号： G03F7/00 , G03F7/004 , G03F7/028 , G03F7/039 , H01L21/027
CPC分类号： G03F7/0045
摘要： A positive-working radiation-sensitive mixture containinga) a compound which generates a strong acid under the action of actinic radiation,b) a compound having at least one C-O-C or C-O-Si bond cleavable by acid andc) a polymeric binder which is insoluble in water and soluble or at least swellable in aqueous alkaline solutions,wherein the compound a) is a 1-sulfonyloxy-2-pyridone, is useful in the preparation of positive-working recording materials.
摘要翻译：一种正性辐射敏感性混合物，其包含a）在光化辐射的作用下产生强酸的化合物，b）具有至少一个可被酸切割的COC或CO-Si键的化合物，和c）聚合物粘合剂，不溶于水，并且在碱性水溶液中可溶或至少可溶胀，其中化合物a）为1-磺酰氧基-2-吡啶酮，可用于制备正性记录材料。

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