公开(公告)号：US07534547B2

公开(公告)日：2009-05-19

申请号：US10296831

申请日：2002-03-29

申请人： Makoto Hanabata ,  Masahiro Sato ,  Junko Katayama ,  Satsuki Kitajima ,  Atsushi Niwa

发明人： Makoto Hanabata ,  Masahiro Sato ,  Junko Katayama ,  Satsuki Kitajima ,  Atsushi Niwa

IPC分类号： G03F7/00 ,  G03F7/004

CPC分类号： C07C317/22 ,  C07C43/303 ,  C07C43/313 ,  C07C43/315 ,  C07C69/92 ,  C07C69/96 ,  C07C271/58 ,  C07C2601/14 ,  C07C2603/18 ,  G03F7/0045 ,  G03F7/0392 ,  Y02P20/55 ,  Y10S430/114

摘要： A photoactive compound is used in combination with a photosensitizer, represented by the following formula (1): A-[(J)m-(X-Pro)]n  (1) wherein A represents a hydrophobic unit comprising at least one kind of hydrophobic groups selected from a hydrocarbon group and a heterocyclic group, J represents a connecting group, X-Pro represents a hydrophilic group protected by a protective group Pro which is removable by light exposure, m represents 0 or 1, and n represents an integer of not less than 1. The protective group Pro may be removable by light exposure in association with the photosensitizer (especially, a photo acid generator), or may be a hydrophobic protective group. The hydrophilic group may be a hydroxyl group or a carboxyl group. The photoactive compound has high sensitivity to a light source of short wavelength beams, for resist application, therefore, the photoactive compound is advantageously used for forming a pattern with high resolution.

摘要翻译： 光活性化合物与由下式（1）表示的光敏剂组合使用：<？in-line-formula description =“In-line Formulas”end =“lead”？> A - [（J）m- （X-Pro）] n（1）<？in-line-formula description =“In-line Formulas”end =“tail”？>其中A表示疏水单元，其包含至少一种选自烃 基团和杂环基团，J表示连接基团，X-Pro表示被保护基团Pro保护的亲水基团，其可通过曝光可除去，m表示0或1，n表示不小于1的整数。 保护基Pro可以通过与光敏剂（特别是光酸产生剂）相关联的曝光而被除去，或者可以是疏水性保护基。 亲水基团可以是羟基或羧基。 光敏化合物对于短波长光束的光源具有高灵敏度，为了抗蚀剂应用，因此光敏化合物有利地用于形成高分辨率的图案。

公开(公告)号：US06921623B2

公开(公告)日：2005-07-26

申请号：US10203032

申请日：2001-12-04

申请人： Makoto Hanabata ,  Masahiro Sato ,  Junko Katayama ,  Satsuki Kitajima

发明人： Makoto Hanabata ,  Masahiro Sato ,  Junko Katayama ,  Satsuki Kitajima

IPC分类号： G03F7/038 ,  G03F7/039 ,  G03F7/075 ,  G03F7/004

CPC分类号： G03F7/0757 ,  G03F7/0382 ,  G03F7/0392

摘要： A photosensitive resin composition for using in combination with a photosensitizer comprises an active component selected from an active metal alkoxide represented by the formula (1) or a polycondensate thereof and a particle represented by the formula (2), (X)m-n-Mm-[(U1)p—(U2-Z)t]n  (1) P—[(Y)s—{(U1)p—(U2-Z)t}]k  (2) wherein, X shows a hydrogen, a halogen, an alkoxy group or an alkoxycarbonyl group, M shows a metal atom whose valence m is not less than 2, U1 shows a first connecting unit, U2 shows a second connecting unit and Z shows a group causing a difference in solubility by light exposure, P shows a fine particle carrier, Y shows a coupling residue, n shows an integer of not less than 1 and m>n, p shows 0 or 1, t shows 1 or 2, k shows an integer of not less than 1, and s shows 0 or 1). The unit (U1)p—(U2-Z)t is represented by the following formula: f(R1)q-(B)r]p-({(R2),,-(Ar)v}-Zlt (wherein, R1 and R2 show an alkylene or alkenylene group; and B shows an ester bond, an amide bond, a urea bond, a urethane bond, an imino group, a sulfur atom or a nitrogen atom; Ar represents an arylene or cycloalkylene group; each of the factors, q, r, a and v, shows 0 or 1, and q+r+u+vzl; and Z, p and t have the same meanings defined above).

公开(公告)号：US4863829A

公开(公告)日：1989-09-05

申请号：US175658

申请日：1988-03-29

申请人： Akihiro Furuta ,  Makoto Hanabata ,  Seimei Yasui ,  Osamu Hiroaki ,  Naoyoshi Jinno

发明人： Akihiro Furuta ,  Makoto Hanabata ,  Seimei Yasui ,  Osamu Hiroaki ,  Naoyoshi Jinno

IPC分类号： G03F7/023

CPC分类号： G03F7/0236

摘要： A positive type photoresist composition comprising a novolak resin and O-quinone diazide compound, the novolak resin being one which is obtained by the addition condensation reaction of a phenol and formaldehyde which is performed in one stage by using as a catalyst an organic acid salt of a divalent metal which is more electropositive than hydrogen, or in two stages by using an acid catalyst in the subsequent stage, the phenol being at least one compound represented by the formula ##STR1## wherein R is hydrogen or an alkyl group of carbon number 1 to 4, the compound being such that the average carbon number in the substituent per one phenol nucelus is 0.5 to 1.5 and the ones with the substituent at the ortho- or para-position with respect to the hydroxyl group account for less than 50 mol %, is disclosed. The positive type photoresist composition of the invention has an improved resolving power, i.e., .gamma.-value.

摘要翻译： 一种正型光致抗蚀剂组合物，其包含酚醛清漆树脂和O-醌二叠氮化合物，所述酚醛清漆树脂是通过苯酚和甲醛的加成缩合反应得到的酚醛清漆树脂，其通过使用作为催化剂在一个阶段中进行的一个阶段中进行的有机酸盐 二价金属，其比氢更正电，或者在后续阶段通过使用酸催化剂分两个阶段，所述酚是至少一种由下式表示的化合物：其中R是氢或碳数为1的烷基 至4，该化合物使得每一个酚醛树脂的取代基中的平均碳数为0.5至1.5，相对于羟基在邻位或对位取代基的平均碳数小于50mol％ ，被披露。 本发明的正型光致抗蚀剂组合物具有改进的分辨能力，即γ值。

公开(公告)号：US5861229A

公开(公告)日：1999-01-19

申请号：US948466

申请日：1992-09-22

申请人： Haruyoshi Osaki ,  Fumio Oi ,  Yasunori Uetani ,  Makoto Hanabata ,  Takeshi Hioki

发明人： Haruyoshi Osaki ,  Fumio Oi ,  Yasunori Uetani ,  Makoto Hanabata ,  Takeshi Hioki

IPC分类号： G03F7/022 ,  G03F7/023

CPC分类号： G03F7/0226 ,  G03F7/0236

摘要： A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:X--.alpha.--H (I)wherein x is a group of the formula: ##STR1## and .alpha. is a divalent group which comprises a repeating unit of the formula: ##STR2## in which n is a number of not less than 1; a, b, c, d, e and f are the same or different and a number of 0-3, provided that d+f is not less than 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or an aryl group, which resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.

摘要翻译： 一种正性抗蚀剂组合物，其包含1,2-醌二叠氮化合物和含有下列通式的多酚化合物（I）的碱溶性树脂：X-α-H（I），其中x是下式的基团： 并且α是包含下式的重复单元的二价基团：其中n是不小于1的数目：或 a，b，c，d，e和f相同或不同，数目为0-3，条件是d + f不小于1; R1，R2和R3相同或不同，C1-C18烷基，C1-C18烷氧基，羧基或卤原子; R4是氢原子，C1-C18烷基或芳基，其抗蚀剂组成对辐射敏感，并具有良好的灵敏度，分辨能力和耐热性的平衡。

公开(公告)号：US5456995A

公开(公告)日：1995-10-10

申请号：US224561

申请日：1994-04-07

申请人： Haruyoshi Ozaki ,  Fumio Oi ,  Yasunori Uetani ,  Makoto Hanabata ,  Takeshi Hioki

发明人： Haruyoshi Ozaki ,  Fumio Oi ,  Yasunori Uetani ,  Makoto Hanabata ,  Takeshi Hioki

IPC分类号： G03F7/022 ,  G03F7/023

CPC分类号： G03F7/0236 ,  G03F7/0226

摘要： A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer represented by the formula: ##STR1## wherein R is C.sub.1-18 or hydrogen, the composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.

摘要翻译： 一种正性抗蚀剂组合物，其包含光敏1,2-醌二叠氮化合物，碱溶性树脂以结合成分和多酚化合物以控制由下式表示的显影剂中的溶解速率：位置对辐射敏感， 具有良好的灵敏度平衡，分辨能力和耐热性。

公开(公告)号：US4414365A

公开(公告)日：1983-11-08

申请号：US356241

申请日：1982-03-08

申请人： Hiroaki Sugimoto ,  Makoto Hanabata

发明人： Hiroaki Sugimoto ,  Makoto Hanabata

IPC分类号： C08G63/60 ,  C08L67/00

CPC分类号： C08G63/605 ,  C08L67/00

摘要： A process for producing an aromatic polyester composition, which is characterized in that in producing an aromatic polyester represented by the general formula A, ##STR1## (wherein X is an alkylene group having 1 to 4 carbon atoms, --O--, --SO.sub.2 --, --S--, or --CO--; m and n are each 0 or 1; the ratio of d to e is in the range of from 1:1 to 10:1; the ratio of e to f is in the range of from 9:10 to 10:9; and the substituents attached to the benzene ring are in para or meta position to one another), the polymerization is carried out by the method of bulk polymerization, using substantially no solvent, and in the presence of at least one polymer selected from the group consisting of polyalkylene terephthalates, polyphenylene sulfides, aromatic polysulfones, and aromatic polyesters represented by the general formula B, ##STR2## wherein (p+q) is in the range of from 10 to 100 and p/(p+q).gtoreq.0.8.

摘要翻译： 一种芳族聚酯组合物的制备方法，其特征在于在制备由通式A表示的芳族聚酯，其中X为具有1至4个碳原子的亚烷基，-O-，-SO 2 - ， - S-或-CO-; m和n各自为0或1; d与e的比例在1：1至10：1的范围内; e与f的比例在 为9:10至10:9;并且与苯环相连的取代基彼此处于对位或间位），聚合通过本体聚合法，基本上不使用溶剂进行，并且在存在下 的至少一种选自聚对苯二甲酸亚烷基酯，聚苯硫醚，芳族聚砜和由通式B表示的芳族聚酯的聚合物，其中（p + q）在10至100的范围内，和 p /（p + q）> / = 0.8。

公开(公告)号：US06183935B2

公开(公告)日：2001-02-06

申请号：US09380641

申请日：1999-09-07

申请人： Makoto Hanabata ,  Tokugen Yasuda

发明人： Makoto Hanabata ,  Tokugen Yasuda

IPC分类号： G03C1492

CPC分类号： G03F7/0042 ,  G03F7/002 ,  G03F7/0047 ,  G03F7/0755

摘要： An inorganic pattern is formed by coating an inorganic substance-containing photosensitive composition comprising a photosensitive polymer (A), a condensable organic metal compound or a condensate thereof (B) and an inorganic filler having a functional group (C) on a base, exposing the coated layer, and developing the exposed layer to form a pattern, baking the pattern give an inorganic pattern. The photosensitive polymer (A) may be constituted of an oligomer or polymer, and a photosensitizer, and the condensable organic metal compound (B) may have a photosensitive group. The inorganic filler may be a monodispersed colloidal silica having a mean particle size of 2 to 100 nm. The proportions of the components (B) and (C) relative to 1 part by weight of the component (A) on a solid basis are about 1 to 25 parts by weight and about 1 to 20 parts by weight, respectively. Even when the content of an inorganic component is high, an inorganic pattern of high resolution can be formed with the use of the above resin composition.

摘要翻译： 通过将含有感光性聚合物（A），可冷凝有机金属化合物或其缩合物（B）的无机物质感光性组合物和具有官能团（C）的无机填充剂涂布在基材上而形成无机图案，曝光 涂覆层，并且显影曝光层以形成图案，烘烤图案得到无机图案。 光敏聚合物（A）可以由低聚物或聚合物和光敏剂构成，并且可冷凝有机金属化合物（B）可以具有感光性基团。 无机填料可以是平均粒径为2〜100nm的单分散的胶体二氧化硅。 组分（B）和（C）相对于基于固体的组分（A）的1重量份的比例分别为约1至25重量份和约1至20重量份。 即使无机成分的含量高，也可以使用上述树脂组合物形成高分辨率的无机图案。

公开(公告)号：US5290656A

公开(公告)日：1994-03-01

申请号：US5429

申请日：1993-01-19

申请人： Yasunori Uetani ,  Makoto Hanabata ,  Hirotoshi Nakanishi ,  Koji Kuwana ,  Yukio Hanamoto ,  Fumio Oi ,  Jun Tomioka

发明人： Yasunori Uetani ,  Makoto Hanabata ,  Hirotoshi Nakanishi ,  Koji Kuwana ,  Yukio Hanamoto ,  Fumio Oi ,  Jun Tomioka

IPC分类号： G03F7/022 ,  G03C1/52 ,  C07C309/76

CPC分类号： G03F7/022

摘要： A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I): ##STR1## wherein Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are the same or different and each a hydrogen atom, an alkyl group, a halogen atom or a hydroxyl group, provided that at least one of Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 is a hydroxyl group; Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 are the same or different and each a hydrogen atom, an alkyl, an aryl group, a halogen atom or a hydroxyl group, provided that at least one of Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 is a hydroxyl group; X is ##STR2## in which R.sub.1 and R.sub.2 are the same or different and each a hydrogen atom, an alkyl group, an alkenyl group, a cyclo-alkyl group, an alkoxy group or an aryl group, provided that when at least one of R.sub.1 and R.sub.2 is a hydrogen atom, an alkyl or aryl group is present at the ortho position to a hydroxyl group which is present at the ortho position to X provides a positive resist composition which has a high .gamma.-value.

摘要翻译： 通式（I）的酚化合物的醌二叠氮磺酸酯：其中Y 1，Y 2，Y 3和Y 4相同或不同，各自为氢原子，烷基，卤素原子 或羟基，条件是Y 1，Y 2，Y 3和Y 4中的至少一个为羟基; Z 1，Z 2，Z 3，Z 4，Z 5和Z 6相同或不同，各自为氢原子，烷基，芳基，卤素原子或羟基，条件是Z1，Z2，Z3，Z4中的至少一个 Z5和Z6是羟基; X为，其中R 1和R 2相同或不同，并且各自为氢原子，烷基，烯基，环烷基，烷氧基或芳基，条件是当至少一个 R1和R2是氢原子，烷基或芳基存在于与X的邻位存在的羟基的邻位，提供具有高γ值的正性抗蚀剂组合物。

公开(公告)号：US5124228A

公开(公告)日：1992-06-23

申请号：US381298

申请日：1989-07-18

申请人： Yasunori Uetani ,  Makoto Hanabata ,  Hirotoshi Nakanishi ,  Koji Kuwana ,  Fumio Oi

发明人： Yasunori Uetani ,  Makoto Hanabata ,  Hirotoshi Nakanishi ,  Koji Kuwana ,  Fumio Oi

IPC分类号： G03F7/022

CPC分类号： G03F7/0226

摘要： A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I) or (II): ##STR1## wherein a, c and d are the same or different and a number of 0 to 3, provided that when a is 0 or 3, b is a number of 0 to 3 or when a is 1 or 2, b is 0, 1 or 2, and a+b and c+d are not less than 2; R and R' are the same or different and an alkyl group or an aryl group provides a positive resist composition having a high .gamma.-value.

公开(公告)号：US4812551A

公开(公告)日：1989-03-14

申请号：US118041

申请日：1987-11-09

申请人： Fumio Oi ,  Haruyoshi Osaki ,  Akihiro Furuta ,  Yukikazu Uemura ,  Takao Ninomiya ,  Yasunori Uetani ,  Makoto Hanabata

发明人： Fumio Oi ,  Haruyoshi Osaki ,  Akihiro Furuta ,  Yukikazu Uemura ,  Takao Ninomiya ,  Yasunori Uetani ,  Makoto Hanabata

IPC分类号： G03C1/72 ,  C08G8/00 ,  C08G8/08 ,  G03F7/023 ,  C08G8/04

CPC分类号： C08G8/00 ,  C08G8/08 ,  G03F7/0236

摘要： A novolak resin for a positive photoresist is provided herein, which resin is produced by the addition condensation reaction of a phenol with formaldehyde. This novolak resin has improved heat resistant and sensitivity properties and the thickness retention of the novolak resins are very high. The novolak resins are characterized in that the area ratio of the gel permeation chromatographic pattern (GPC) as measured by the use of a UV(254 nm) detector, is as follows: a range wherein the molecular weight, calculated as polystyrene, is from 150 to less than 500, not including a phenol and the unreacted monomer, is from 8 to 35%, hereinafter referred to as an A region, the range wherein the molecular weight calculated as polystyrene is from 500 to less than 5000 is from 0 to 30%, hereinafter referred to as a B region, and the range wherein the molecular weight calculated as polystyrene exceeds 5000 is from 35 to 92%, hereinafter referred to as the C region, and wherein the ratio of the B region to the A region is 2.50 or less.

摘要翻译： 本文提供了一种用于正性光致抗蚀剂的酚醛清漆树脂，该树脂通过苯酚与甲醛的加成缩合反应制备。 该酚醛清漆树脂具有改善的耐热性和灵敏度性能，并且酚醛清漆树脂的厚度保持率非常高。 酚醛清漆树脂的特征在于通过使用UV（254nm）检测器测量的凝胶渗透色谱图（GPC）的面积比如下：其中以聚苯乙烯计算的分子量来自 150〜小于500，不包括苯酚和未反应单体，为8〜35％，以下称为A区，其中以聚苯乙烯计算的分子量为500〜5000以下的范围为0〜 30％，以下称为B区，其中以聚苯乙烯计算的分子量超过5000的范围为35〜92％，以下称为C区，其中B区与A区的比例 是2.50以下。