公开(公告)号：US5902713A

公开(公告)日：1999-05-11

申请号：US762920

申请日：1996-12-10

申请人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano ,  Kiyoshi Ishikawa

发明人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano ,  Kiyoshi Ishikawa

IPC分类号： C09K3/00 ,  G03F7/004 ,  G03F7/033 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  G03C5/00

CPC分类号： G03F7/038 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/12 ,  Y10S430/122

摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.

公开(公告)号：US6022666A

公开(公告)日：2000-02-08

申请号：US236567

申请日：1999-01-26

申请人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano

发明人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano

IPC分类号： C09K3/00 ,  G03F7/004 ,  G03F7/033 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  G03C1/492

CPC分类号： G03F7/038 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/12 ,  Y10S430/122

摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.

摘要翻译： 公开了能够赋予高分辨率的高耐热图案化抗蚀剂层的新型高灵敏度正负工作化学增感光致抗蚀剂组合物，而不受驻波的影响，具有非常正交的横截面轮廓。 该组合物通过用光化射线照射作为酸产生剂含有特定的氰基取代的肟磺酸酯化合物，例如α-（甲基磺酰氧基亚氨基）-4-甲氧基苄基氰化物。 当成膜树脂成分具有使重均分子量与数均分子量的比例不超过3.5的分子量分布时，通过使用该特定酸产生剂获得的优点是显着的。

公开(公告)号：US5990338A

公开(公告)日：1999-11-23

申请号：US179817

申请日：1998-10-28

申请人： Hideo Hada ,  Yoshiki Sugeta ,  Hiroyuki Yamazaki ,  Hiroshi Komano

发明人： Hideo Hada ,  Yoshiki Sugeta ,  Hiroyuki Yamazaki ,  Hiroshi Komano

IPC分类号： C07C307/02 ,  C07C309/65 ,  C07C309/66 ,  C07C309/73 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  C07C255/00

CPC分类号： C07C309/66 ,  C07C309/65 ,  C07C309/73 ,  G03F7/0045

摘要： Disclosed is a novel positive-working or negative-working chemical-sensitization photoresist composition useful in the photolithographic patterning works for the manufacture of electronic devices. The photoresist composition is characterized by a unique acid-generating agent capable of releasing an acid by the pattern-wise exposure of the resist layer to actinic rays so as to increase or decrease the solubility of the resist layer in an aqueous alkaline developer solution. The acid-generating agent proposed is a novel cyano group-containing oxime sulfonate di- or triester compound represented by the general formulaA[C(CN).dbd.N--O--SO.sub.2 --R].sub.n,in which each R is, independently from the others, an unsubstituted or substituted monovalent hydrocarbon group such as alkyl groups, A is a divalent or tervalent organic group or, preferably, phenylene group and the subscript n is 2, when A is a divalent group, or 3, when A is a tervalent group or, preferably 2. Since more than one of sulfonic acid molecules are released from one molecule of the sulfonate compound by the exposure to actinic rays, the chemical-sensitization photoresist composition exhibits high photosensitivity.

摘要翻译： 公开了一种用于制造电子器件的光刻图案化工艺中的新型正性或负性化学增感光致抗蚀剂组合物。 光致抗蚀剂组合物的特征在于能够通过抗蚀剂层与光化射线的图案曝光而释放酸的独特的酸产生剂，从而增加或降低抗蚀剂层在碱性显影剂水溶液中的溶解度。 所提出的酸产生剂是由通式A [C（CN）= NO-SO 2 -R] n表示的新的含氰基的肟磺酸酯二酯或三酯化合物，其中每个R独立地为 未取代或取代的一价烃基如烷基，A是二价或三价有机基团，或优选亚苯基，下标n为2，当A为二价基团时，或3，当A为三价基团或 ，优选2.由于通过暴露于光化射线，一个以上的磺酸分子从一分子的磺酸酯化合物中释放出来，化学增感光致抗蚀剂组合物表现出高的光敏性。

公开(公告)号：US5973187A

公开(公告)日：1999-10-26

申请号：US179818

申请日：1998-10-28

申请人： Hideo Hada ,  Yoshiki Sugeta ,  Hiroyuki Yamazaki ,  Hiroshi Komano

发明人： Hideo Hada ,  Yoshiki Sugeta ,  Hiroyuki Yamazaki ,  Hiroshi Komano

IPC分类号： C07C307/02 ,  C07C309/65 ,  C07C309/66 ,  C07C309/73 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  C07C255/00

CPC分类号： C07C309/66 ,  C07C309/65 ,  C07C309/73 ,  G03F7/0045

摘要： Disclosed is a novel positive-working or negative-working chemical-sensitization photoresist composition useful in the photolithographic patterning works for the manufacture of electronic devices. The photoresist composition is characterized by a unique acid-generating agent capable of releasing an acid by the pattern-wise exposure of the resist layer to actinic rays so as to increase or decrease the solubility of the resist layer in an aqueous alkaline developer solution. The acid-generating agent proposed is a novel cyano group-containing oxime sulfonate di- or triester compound represented by the general formulaA[C(CN).dbd.N--O--SO.sub.2 --R].sub.n,in which each R is, independently from the others, an unsubstituted or substituted monovalent hydrocarbon group such as alkyl groups, A is a divalent or tervalent organic group or, preferably, phenylene group and the subscript n is 2, when A is a divalent group, or 3, when A is a tervalent group or, preferably 2. Since more than one of sulfonic acid molecules are released from one molecule of the sulfonate compound by the exposure to actinic rays, the chemical-sensitization photoresist composition exhibits high photosensitivity.

摘要翻译： 公开了一种用于制造电子器件的光刻图案化工艺中的新型正性或负性化学增感光致抗蚀剂组合物。 光致抗蚀剂组合物的特征在于能够通过抗蚀剂层与光化射线的图案曝光而释放酸的独特的酸产生剂，从而增加或降低抗蚀剂层在碱性显影剂水溶液中的溶解度。 所提出的酸产生剂是由通式A [C（CN）= NO-SO 2 -R] n表示的新的含氰基的肟磺酸酯二酯或三酯化合物，其中每个R独立地为 未取代或取代的一价烃基如烷基，A是二价或三价有机基团，或优选亚苯基，下标n为2，当A为二价基团时，或3，当A为三价基团或 ，优选2.由于通过暴露于光化射线，一个以上的磺酸分子从一分子的磺酸酯化合物中释放出来，化学增感光致抗蚀剂组合物表现出高的光敏性。

公开(公告)号：US6063953A

公开(公告)日：2000-05-16

申请号：US236612

申请日：1999-01-26

申请人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano

发明人： Hideo Hada ,  Hiroyuki Yamazaki ,  Yoshiki Sugeta ,  Hiroshi Komano

IPC分类号： C09K3/00 ,  G03F7/004 ,  G03F7/033 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  C07C255/07

CPC分类号： G03F7/038 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/12 ,  Y10S430/122

摘要： Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.

公开(公告)号：US6077644A

公开(公告)日：2000-06-20

申请号：US207202

申请日：1998-12-08

申请人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano ,  Toshimasa Nakayama

发明人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano ,  Toshimasa Nakayama

IPC分类号： C07C69/013 ,  G03F7/004 ,  G03F7/039

CPC分类号： C07C69/013 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/115 ,  Y10S430/122

摘要： Proposed is a novel chemical-sensitization positive-working photoresist composition used in the photolithographic patterning process for the manufacture of fine electronic devices, which is capable of giving, with high photosensitivity to ArF excimer laser beams, a patterned resist layer having an excellently orthogonal cross sectional profile and high resistance against dry etching and exhibiting good adhesion to the substrate surface. While the composition comprises (A) a film-forming resinous ingredient which undergoes an increase of alkali solubility by interacting with an acid and (B) a radiation-sensitive acid-generating agent, the most characteristic feature of the invention consists in the use of a specific acrylic resin as the component (A), which comprises the monomeric units of a (meth)acrylic acid ester of hydroxy bicyclo[3.1.1]heptanone unsubstituted or substituted by an alkyl group such as hydroxypinanone (meth)acrylate, optionally, in combination with the monomeric units derived from (meth)acrylic acid and/or tert-butyl (meth)acrylate in a molar fraction of 3:7 to 7:3.

摘要翻译： 提出了用于制造精细电子器件的光刻图案化工艺中的新型化学增感正性光致抗蚀剂组合物，其能够赋予ArF准分子激光束具有高光敏性的具有良好正交交叉的图案化抗蚀剂层 截面轮廓和高抗干蚀刻性，并且对基材表面具有良好的粘合性。 虽然组合物包含（A）通过与酸相互作用而增加碱溶解度的成膜树脂成分和（B）辐射敏感的酸产生剂，但是本发明的最特征在于使用 作为组分（A）的特定丙烯酸树脂，其包含未被取代或被烷基如羟基酮（甲基）丙烯酸酯取代的羟基双环[3.1.1]庚酮的（甲基）丙烯酸酯的单体单元， 与来自（甲基）丙烯酸和/或（甲基）丙烯酸叔丁酯的单体单元组合，摩尔分数为3:7至7:3。

公开(公告)号：US5892095A

公开(公告)日：1999-04-06

申请号：US791814

申请日：1997-01-30

申请人： Hideo Hada ,  Hiroshi Komano ,  Toshimasa Nakayama

发明人： Hideo Hada ,  Hiroshi Komano ,  Toshimasa Nakayama

IPC分类号： C07C307/02 ,  C07C309/65 ,  C07C309/66 ,  C07C309/73 ,  G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027 ,  C07C255/00 ,  G03F5/16 ,  G03F7/022

CPC分类号： C07C309/66 ,  C07C309/65 ,  C07C309/73 ,  G03F7/0045

摘要： Disclosed is a novel positive-working or negative-working chemical-sensitization photoresist composition useful in the photolithographic patterning works for the manufacture of electronic devices. The photoresist composition is characterized by a unique acid-generating agent capable of releasing an acid by the pattern-wise exposure of the resist layer to actinic rays so as to increase or decrease the solubility of the resist layer in an aqueous alkaline developer solution. The acid-generating agent proposed is a novel cyano group-containing oxime sulfonate di- or triester compound represented by the general formulaA�C(CN).dbd.N--O--SO.sub.2 --R!.sub.n,in which each R is, independently from the others, an unsubstituted or substituted monovalent hydrocarbon group such as alkyl groups, A is a divalent or tervalent organic group or, preferably, phenylene group and the subscript n is 2, when A is a divalent group, or 3, when A is a tervalent group or, preferably 2. Since more than one of sulfonic acid molecules are released from one molecule of the sulfonate compound by the exposure to actinic rays, the chemical-sensitization photoresist composition exhibits high photosensitivity.

摘要翻译： 公开了一种用于制造电子器件的光刻图案化工艺中的新型正性或负性化学增感光致抗蚀剂组合物。 光致抗蚀剂组合物的特征在于能够通过抗蚀剂层与光化射线的图案曝光而释放酸的独特的酸产生剂，从而增加或降低抗蚀剂层在碱性显影剂水溶液中的溶解度。 所提出的酸产生剂是由通式A [C（CN）= NO-SO 2 -R] n表示的新的含氰基的肟磺酸酯二酯或三酯化合物，其中每个R独立地为 未取代或取代的一价烃基如烷基，A是二价或三价有机基团，或优选亚苯基，下标n为2，当A为二价基团时，或3，当A为三价基团或 ，优选2.由于通过暴露于光化射线，一个以上的磺酸分子从一分子的磺酸酯化合物中释放出来，化学增感光致抗蚀剂组合物表现出高的光敏性。

公开(公告)号：US06388101B1

公开(公告)日：2002-05-14

申请号：US09562458

申请日：2000-05-02

申请人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano

发明人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano

IPC分类号： C07D30512

CPC分类号： C07D307/33 ,  G03F7/0392 ,  Y02P20/55

摘要： Proposed is a chemical-sensitization positive-working photoresist composition for photolithographic patterning in the manufacture of semiconductor devices having high transparency even to ultraviolet light of very short wavelength such as ArF excimer laser beams of 193 nm wavelength to exhibit high photosensitivity and capable of giving a patterned resist layer with high pattern resolution. The composition comprises (A) a resinous ingredient which is subject to an increase of the solubility in an aqueous alkaline developer solution in the presence of an acid and (B) a radiation-sensitive acid-generating compound. Characteristically, the resinous ingredient as the component (A) is a (meth)acrylic copolymer of which from 20% to 80% by moles of the monomeric units are derived from a (meth)acrylic acid ester of which the ester-forming group has a specific oxygen-containing heterocyclic ring structure.

摘要翻译： 提出了一种用于制造半导体器件的化学增感正性光致抗蚀剂组合物，即使对于非常短波长的紫外光也具有高透明度，例如193nm波长的ArF准分子激光束，以显示高光敏性，并且能够给出 具有高图案分辨率的图案化抗蚀剂层。 组合物包含（A）在酸的存在下在碱性显影剂水溶液中溶解度增加的树脂成分和（B）辐射敏感的产酸化合物。 特征在于，作为（A）成分的树脂成分是（甲基）丙烯酸系共聚物，20〜80摩尔％的单体单元衍生自成酯基的（甲基）丙烯酸酯 特定的含氧杂环结构。

公开(公告)号：US5929271A

公开(公告)日：1999-07-27

申请号：US912123

申请日：1997-08-15

申请人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano ,  Toshimasa Nakayama

发明人： Hideo Hada ,  Kazufumi Sato ,  Hiroshi Komano ,  Toshimasa Nakayama

IPC分类号： C07C69/013 ,  G03F7/004 ,  G03F7/039 ,  C07C69/74

CPC分类号： C07C69/013 ,  G03F7/0045 ,  G03F7/039 ,  Y10S430/115 ,  Y10S430/122

摘要： Proposed is novel compounds for use in a chemical-sensitization positive-working photoresist composition used in the photolithographic patterning process for the manufacture of fine electronic devices, which is capable of giving, with high photosensitivity to ArF excimer laser beams, a patterned resist layer having an excellently orthogonal cross sectional profile and high resistance against dry etching and exhibiting good adhesion to the substrate surface. While the composition comprises (A) a film-forming resinous ingredient which causes an increase of alkali solubility by interacting with an acid and (B) a radiation-sensitive acid-generating agent, the most characteristic feature of the invention consists in the use of a specific acrylic resin as the component (A), which comprises the monomeric units of a (meth)acrylic acid ester of hydroxy bicyclo�3.1.1!heptanone unsubstituted or substituted by an alkyl group such as hydroxypinanone (meth)acrylate, optionally, in combination with the monomeric units derived from (meth)acrylic acid and/or tert-butyl (meth)acrylate in a molar fraction of 3:7 to 7:3.

摘要翻译： 提出了用于制造精细电子器件的光刻图案化方法中使用的化学增感正性光致抗蚀剂组合物中的新化合物，其能够赋予ArF准分子激光束具有高光敏性的图案化抗蚀剂层，其具有 具有优异的正交横截面轮廓和高耐干腐蚀性，并且对基材表面表现出良好的粘合性。 虽然组合物包含（A）通过与酸相互作用引起碱溶解度增加的成膜树脂成分和（B）辐射敏感的酸产生剂，但是本发明的最特征在于使用 作为组分（A）的特定丙烯酸树脂，其包含未被取代或被烷基如羟基酮（甲基）丙烯酸酯取代的羟基双环[3.1.1]庚酮的（甲基）丙烯酸酯的单体单元， 与来自（甲基）丙烯酸和/或（甲基）丙烯酸叔丁酯的单体单元组合，摩尔分数为3:7至7:3。

公开(公告)号：US5800964A

公开(公告)日：1998-09-01

申请号：US717779

申请日：1996-09-24

申请人： Mitsuru Sato ,  Kazuyuki Nitta ,  Hideo Hada ,  Tatsuya Hashiguchi ,  Hiroshi Komano ,  Toshimasa Nakayama

发明人： Mitsuru Sato ,  Kazuyuki Nitta ,  Hideo Hada ,  Tatsuya Hashiguchi ,  Hiroshi Komano ,  Toshimasa Nakayama

IPC分类号： G03F7/004 ,  G03F7/038 ,  G03F7/039 ,  H01L21/027

CPC分类号： G03F7/0045 ,  Y10S430/12 ,  Y10S430/122

摘要： Disclosed is a novel and improved photoresist composition which comprises: (A) a film-forming resinous compound which is, in the presence of an acid, subject to a change in the solubility in an alkaline solution; and (B) an acid-generating agent capable of releasing an acid by the exposure to actinic rays which is an oxime sulfonate compound represented by the general formula NC--CR.sup.1 .dbd.N--O--SO.sub.2 --R.sup.2, in which R.sup.1 and R.sup.2 are, each independently from the other, an unsubstituted or halogen-substituted monovalent aliphatic hydrocarbon group, e.g., alkyl, cycloalkyl, alkenyl and cycloalkenyl groups. By virtue of the non-aromatic nature of the component (B) as well as good solubility thereof in organic solvents and high acid strength of the acid released therefrom, the composition is highly transparent to deep ultraviolet light even when the content of the component (B) is relatively large and the photosensitivity of the composition is very high so that the photoresist composition is capable of giving a patterned resist layer having excellent characteristics.

摘要翻译： 公开了一种新颖且改进的光致抗蚀剂组合物，其包含：（A）在酸存在下，在碱溶液中溶解度变化的成膜树脂化合物; 和（B）能够通过暴露于由通式NC-CR1 = NO-SO2-R2表示的肟磺酸盐化合物的光化射线释放酸的酸产生剂，其中R 1和R 2各自独立地为 另一个，未取代或卤素取代的一价脂族烃基，例如烷基，环烷基，烯基和环烯基。 由于组分（B）的非芳香性质以及其在有机溶剂中的良好溶解性和从其释放的酸的高酸强度，组合物对于深紫外光是高度透明的，即使组分（ B）相对较大并且组合物的光敏性非常高，使得光致抗蚀剂组合物能够提供具有优异特性的图案化抗蚀剂层。