公开(公告)号：US06255405B1

公开(公告)日：2001-07-03

申请号：US09424128

申请日：2000-03-23

申请人： Wen-Bing Kang ,  Yoshinori Nishiwaki ,  Ken Kimura ,  Syoko Matsuo ,  Hatsuyuki Tanaka

发明人： Wen-Bing Kang ,  Yoshinori Nishiwaki ,  Ken Kimura ,  Syoko Matsuo ,  Hatsuyuki Tanaka

IPC分类号： C08F12008

CPC分类号： G03F7/091 ,  C08F8/14 ,  C08F8/30 ,  C09D5/32 ,  C08F220/00

摘要： A high-performance anti-reflective coating which highly absorbs a given light, e.g., deep ultraviolet rays, tenaciously adheres to substrates upon coating formation, is satisfactory in covering, and eliminates the influence of standing waves in the production of integrated circuits; novel light-absorbing polymers for forming the anti-reflective coating; and a process for producing the polymers. One of the polymers is produced by esterifying a copolymer comprising carboxylic anhydride groups and/or dicarboxylic acid groups such as maleic acid as basic recurring units with a hydroxylated aromatic chromophore. The unreacted carboxylic acid groups or acid anhydride groups remaining in the esterified light-absorbing polymer may be amidated and/or imidized with an aminated aromatic compound. Each of these polymers is dissolved in an organic solvent comprising an alcohol, aromatic hydrocarbon, ketone, ester, or combination of these, and the solution is applied to a substrate and then baked to form an anti-reflective coating.

摘要翻译： 在涂层形成时，高度吸收给定光（例如深紫外线）强力粘附于基材的高性能抗反射涂层在覆盖时是令人满意的，并且消除驻波在集成电路生产中的影响; 用于形成抗反射涂层的新型光吸收聚合物; 和聚合物的制造方法。 其中一种聚合物是通过将包含羧酸酐基团和/或二羧酸基团如马来酸的共聚物作为碱性重复单元与羟基化芳族发色团酯化而制备的。 残留在酯化光吸收聚合物中的未反应的羧酸基团或酸酐基团可以用胺化芳族化合物酰胺化和/或酰亚胺化。 将这些聚合物中的每一种溶解在包含醇，芳族烃，酮，酯或它们的组合的有机溶剂中，并将溶液施加到基材上，然后烘焙以形成抗反射涂层。

公开(公告)号：US06939661B2

公开(公告)日：2005-09-06

申请号：US10232081

申请日：2002-08-30

申请人： Wen-Bing Kang ,  Ken Kimura ,  Shoko Matsuo ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

发明人： Wen-Bing Kang ,  Ken Kimura ,  Shoko Matsuo ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

IPC分类号： C08G18/80 ,  C09D175/04 ,  G03F7/09 ,  G03F7/004

CPC分类号： C08G18/80 ,  C09D175/04 ,  G02B1/111 ,  G03F7/091 ,  Y10S430/106 ,  Y10S430/107 ,  Y10S430/108 ,  Y10S430/115 ,  Y10S430/151

摘要： A composition for forming a radiation absorbing coating which comprises an organic solvent, a radiation absorbing polymer or a radiation absorbing material dissolved therein and a crosslinking agent having blocked isocyanate groups. Since the isocyanate groups of the crosslinking agent have been blocked, the composition containing the crosslinking agent has excellent storage stability. When the composition applied to a substrate and then baked, crosslinking proceeds to give an antireflective coating, which does not intermix with a resist layer to be formed thereon by coating and is free from diffusion of a photo-generated acid thereinto from the resist layer. As a result, a resist image free from footing or scum can be formed.

摘要翻译： 一种用于形成辐射吸收涂层的组合物，其包含溶解在其中的有机溶剂，辐射吸收聚合物或辐射吸收材料以及具有封闭的异氰酸酯基团的交联剂。 由于交联剂的异氰酸酯基团已经被阻断，所以含有交联剂的组合物具有优异的储存稳定性。 当将组合物施加到基底上然后烘烤时，进行交联以得到抗反射涂层，其不与通过涂覆在其上形成的抗蚀剂层混合，并且其中没有光抗蚀剂层中的光产生的酸的扩散。 结果，可以形成没有基脚或浮渣的抗蚀剂图像。

公开(公告)号：US06465148B1

公开(公告)日：2002-10-15

申请号：US09486843

申请日：2000-05-23

申请人： Wen-Bing Kang ,  Ken Kimura ,  Shoko Matsuo ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

发明人： Wen-Bing Kang ,  Ken Kimura ,  Shoko Matsuo ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

IPC分类号： G03C173

CPC分类号： C08G18/80 ,  C09D175/04 ,  G02B1/111 ,  G03F7/091 ,  Y10S430/106 ,  Y10S430/107 ,  Y10S430/108 ,  Y10S430/115 ,  Y10S430/151

摘要： A composition for forming a radiation absorbing coating which comprises an organic solvent, a radiation absorbing polymer or a radiation absorbing material dissolved therein and a crosslinking agent having blocked isocyanate groups. Since the isocyanate groups of the crosslinking agent have been blocked, the composition containing the crosslinking agent has excellent storage stability. When the composition applied to a substrate and then baked, crosslinking proceeds to give an antireflective coating, which does not intermix with a resist layer to be formed thereon by coating and is free from diffusion of a photo-generated acid thereinto from the resist layer. As a result, a resist image free from footing or scum can be formed.

摘要翻译： 一种用于形成辐射吸收涂层的组合物，其包含溶解在其中的有机溶剂，辐射吸收聚合物或辐射吸收材料以及具有封闭的异氰酸酯基团的交联剂。 由于交联剂的异氰酸酯基团已经被阻断，所以含有交联剂的组合物具有优异的储存稳定性。 当将组合物施加到基底上然后烘烤时，进行交联以得到抗反射涂层，其不与通过涂覆在其上形成的抗蚀剂层混合，并且其中没有光抗蚀剂层中的光产生的酸的扩散。 结果，可以形成没有基脚或浮渣的抗蚀剂图像。

公开(公告)号：US06465161B1

公开(公告)日：2002-10-15

申请号：US09600612

申请日：2000-07-17

申请人： Wen-Bing Kang ,  Shoko Matsuo ,  Ken Kimura ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

发明人： Wen-Bing Kang ,  Shoko Matsuo ,  Ken Kimura ,  Yoshinori Nishiwaki ,  Hatsuyuki Tanaka

IPC分类号： G03F700

CPC分类号： G03F7/16 ,  G03F7/0045 ,  G03F7/091

摘要： In a process for manufacturing integrated circuit elements or the like by photolithography, a method for reducing detrimental influence on resist shape due to properties of a substrate or acidity of substrate surface in case where a chemically amplified resist or the like is used as a photoresist, and a substrate-treating agent composition to be used for this method are described. The substrate-treating agent composition comprises a solution containing a salt between at least one basic compound selected from among primary, secondary and tertiary amines and nitrogen-containing heterocyclic compounds and an organic acid such as a sulfonic acid or a carboxylic acid. This composition is coated on a substrate surface having thereon a bottom anti-reflective coating such as SiON layer, baked and, if necessary washed, then a chemically amplified resist is coated on the thus-treated substrate, exposed and developed to form a resist pattern on the substrate.

摘要翻译： 在通过光刻制造集成电路元件等的方法中，使用化学放大型抗蚀剂等作为光致抗蚀剂的情况下，由于基板性质或基板表面的酸度降低对抗蚀剂形状的有害影响的方法， 并描述用于该方法的底物处理剂组合物。 底物处理剂组合物包含含有至少一种选自伯胺，仲胺和叔胺的碱性化合物和含氮杂环化合物之间的盐和有机酸如磺酸或羧酸的溶液。 将该组合物涂布在其上具有诸如SiON层的底部抗反射涂层的基底表面上，烘烤并且如果需要洗涤，然后将化学放大的抗蚀剂涂覆在如此处理的基底上，暴露并显影以形成抗蚀剂图案 在基板上。

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。

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。

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。

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。

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。

公开(公告)号：US06184305B2

公开(公告)日：2001-02-06

申请号：US09079565

申请日：1998-05-15

申请人： Wen-Bing Kan ,  Akihiko Tokida ,  Kayo Aramaki ,  Hatsuyuki Tanaka ,  Ken Kimura

发明人： Wen-Bing Kan ,  Akihiko Tokida ,  Kayo Aramaki ,  Hatsuyuki Tanaka ,  Ken Kimura

IPC分类号： C08F2008

CPC分类号： C08F8/34 ,  C08F8/30 ,  C09D5/32 ,  G03F7/091

摘要： A radiation absorbing polymer is characterized by having a main chain copolymer containing recurring units of dicarboxylic acid or carboxylic anhydride group with an organic chromophore bonded to the carboxyl group through methylene or alkylene linkage group, where the organic chromophore is bonded to the carboxyl group by esterification reaction. Residual carboxyl groups of the radiation absorbing polymer can optionally be amidized and/or imidized with an aromatic compounds having a reactive amino group. When the photoresist is applied on the antireflective coating and is exposed by radiation such as deep ultraviolet radiation, a resist pattern with high resolving power is formed, which is not affected by standing wave upon manufacturing integrated circuit elements.

摘要翻译： 辐射吸收聚合物的特征在于具有含有二羧酸或羧酸酐基团的重复单元的主链共聚物和通过亚甲基或亚烷基连接基与羧基键合的有机发色团，其中有机发色团通过酯化键合到羧基上 反应。 辐射吸收聚合物的残余羧基可以任选地被具有反应性氨基的芳族化合物酰胺化和/或酰亚胺化。 当光致抗蚀剂被施加在抗反射涂层上并且通过诸如深紫外线辐射的辐射曝光时，形成具有高分辨能力的抗蚀剂图案，其在制造集成电路元件时不受驻波的影响。