WO2001073512A1 - Composition de resist positif du type a amplification chimique - Google Patents
Composition de resist positif du type a amplification chimique Download PDFInfo
- Publication number
- WO2001073512A1 WO2001073512A1 PCT/JP2001/002246 JP0102246W WO0173512A1 WO 2001073512 A1 WO2001073512 A1 WO 2001073512A1 JP 0102246 W JP0102246 W JP 0102246W WO 0173512 A1 WO0173512 A1 WO 0173512A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- adamantyl
- acrylate
- resin
- hydroxystyrene
- Prior art date
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Definitions
- the present invention relates to a resist composition suitable for lithography and the like, which is acted on by high-energy radiation such as deep ultraviolet rays (including excimer lasers), electron beams, X-rays, or emitted light.
- high-energy radiation such as deep ultraviolet rays (including excimer lasers), electron beams, X-rays, or emitted light.
- a chemically amplified positive resist is a poly (hydroxystyrene) -based resin, and some of its phenolic hydroxyl groups are cleaved by the action of acid.
- a resin protected with an acid generator is used in combination with an acid generator.
- a group that is cleaved by the action of such an acid a group that forms an acetal-type bond with an oxygen atom derived from a phenolic hydroxyl group from the viewpoint of resolution, sensitivity, and the like, for example, tetrahydro-2-pyrael
- An object of the present invention is to provide a chemically amplified positive electrode having excellent performances such as sensitivity, resolution, heat resistance, remaining film ratio, coating properties, exposure allowance, and drying resistance, and in particular, further improved resolution and exposure allowance. It is an object of the present invention to provide a mold resist composition.
- the inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, as a resin component of a chemically amplified poly-type resist, 3-hydroxy-11-adamantyl acrylate and 3,5- (meth) acrylic acid 3,5-
- the present inventors have found that excellent performance can be obtained by using at least one type of Z-hydroxystyrene-based copolymer selected from dihydroxy-1-adamantyl, and completed the present invention. Disclosure of the invention
- the present invention relates to a polymerization unit of at least one selected from a polymerization unit of 3-hydroxy-1-adamantyl acrylate and a polymerization unit of 3,5-dihydroxy-11-adamantyl (meth) acrylate, a polymerization unit of hydroxystyrene, and an acid. It has a polymerized unit with an unstable group, and is itself insoluble or hardly soluble in alkali.However, after the acid-labile group is cleaved by the action of acid, An object of the present invention is to provide a chemically amplified positive resist composition characterized by containing a resin to be dissolved and an acid generator.
- the resin component that is the main component in the resist composition of the present invention is insoluble or hardly soluble in alkali metal by itself, but undergoes a chemical change by the action of an acid to become alkali-soluble, It has at least two kinds of polymerized units of hydroxystyrene, polymerized units of 3-hydroxy-1-adamantyl acrylate and at least one polymerized unit selected from polymerized units of 3,5-dihydroxy-1-adamantyl (meth) acrylate. .
- Each of these polymerized units is styrene Is formed by opening the double bond of the moieties and the double bond of the (meth) acrylic acid moiety. Specifically, they can be represented by the following formulas (I) and (Ila) to (lie), respectively. it can be represented by the following formulas (I) and (Ila) to (lie), respectively. it can be represented by the following formulas (I) and (Ila) to (lie), respectively. it can be represented by the following formulas (
- the positional relationship between the hydroxyl group and the vinyl group is not particularly limited, but is generally ⁇ ⁇ ⁇ ⁇ ⁇ -hydroxystyrene. It is insoluble or hardly soluble in water, but has a polymerized unit having an acid-labile group because it undergoes a chemical change by the action of an acid to become alkali-soluble, and the acid-labile group is usually a hydroxyl group
- the acid-labile group for protecting the alkali-soluble group is introduced into the resin in a form that protects the alkali-soluble group such as thiol-oxyl group and the like.
- Tert-butyl, tert-butoxycarbonyl the following formula (III) R 1
- R 1 represents alkyl having 1 to 4 carbons
- R 2 represents alkyl having 1 to 6 carbons or cycloalkyl having 5 to 7 carbons
- R 1 and R 2 are taken together.
- R 3 represents alkyl having 1 to 4 carbons
- Suitable as the acetal group represented by the formula (III) include tetrahydro-2-furyl, tetrahydro-2-pyranyl, 1-ethoxyxyl, 1-isopropoxyl, 1-isobutoxethyl, 1-ethoxypropyl, and 1-ethoxypropyl.
- Suitable 2-alkyl-2-adamantyl represented by the formula (IV) include 2-methyl-2-adamantyl, 2-ethyl-2-adamantyl and the like.
- tert-butoxycarbonyl is usually substituted with a hydroxyl group
- 2-alkyl-12-adamantyl represented by the formula (IV) is usually substituted with a carboxyl group.
- Other tert-butyl and acetal-based groups represented by the formula (III) can be substituted with any of a hydroxyl group and a carbonyl group.
- the acid-stable group is generally in the form of protecting the hydroxyl group of the hydroxystyrene unit.
- a unit in which an acid labile group is bonded to the hydroxyl group of the hydroxystyrene unit can be represented by the following formula (V).
- Q represents an acid-labile group.
- Specific examples of Q in this formula include tert-butyl, tert-butoxycarbonyl, and acetal-based groups represented by the above formula ( ⁇ ), and among them, Q is preferably represented by the above formula (III).
- This preferred embodiment can be represented by the following formula (VI) as a polymerized unit.
- R ′ and R 2 are as defined above in formula (III).
- R 1 in the formula (II I) or (VI) is alkyl having 1 to 4 carbons
- R 2 is alkyl having 1 to 6 carbons or 5 to 7 carbons.
- cycloalkyl is alkyl having 1 to 6 carbons or 5 to 7 carbons.
- the resin having a polymerized unit having an acid-labile group can be produced, for example, as follows.
- the acid-labile group is tert-butyl, which replaces the hydroxyl group of hydroxystyrene, tert-butoxystyrene and acrylate 3-hydroxy-1-adamantyl and (meth) acrylate 3, It can be produced by copolymerizing at least one selected from 5-dihydroxy-1-adamantyl by a conventional method, and then appropriately hydrolyzing to partially convert a tert-butoxy group to a hydroxyl group.
- the acid-labile group is tert-butoxycarbonyl, which substitutes for the hydroxyl group of hydroxystyrene, hydroxystyrene and acrylic acid 3-hydroxy-1-adamantyl and (meth) acrylic acid 3,5-
- the copolymer with at least one selected from dihydroxy_1-adamantyl is di-carbonate di-tert- It can be produced by reacting butyl.
- R 5 -C CH-0-R 2 (Ma)
- R 2 is as defined above, and R 4 and each independently represent hydrogen or alkyl, and the total carbon number of both is 0 to 3, or R 5 is hydrogen. And R 2 and R 4 together form a trimethylene or tetramethylene chain)
- acid-labile groups include tert-butyl, acetal-based groups represented by the formula (III), 2-alkyl-2-adamantyl represented by the formula (IV), and the like.
- the unsaturated compound forming a carboxylic acid ester with these groups is usually replaced with hydroxystyrene and 3-hydroxy-1-adamantyl acrylate and 3,5-dihydroxy-1-adamanacrylate (meth) acrylate. It can be produced by copolymerizing with at least one selected from chill.
- Unsaturated compounds which form carboxylic esters with acid-labile groups include unsaturated aliphatic esters such as acrylates and methacrylates, norbornene carboxylate, and tricyclodecene carboxylate. And unsaturated cycloaliphatic esters such as acid esters and tetracyclodecene sulfonic acid esters.
- Hydroxystyrene or ter-butoxystyrene and at least one selected from 3-hydroxy-11-adamantyl acrylate and 3,5-dihydroxy-1-adamantyl (meth) acrylate, and optionally, an acid-labile group Copolymerization using a monomer having and or other monomers can be carried out according to a conventional method. For example, a raw material monomer is dissolved in an appropriate solvent, and a polymerization initiator is added thereto. In addition, a method in which polymerization is started and the reaction is continued under heating or heat removal can be adopted.
- reaction solvent examples include alcohols such as methanol, ethanol, 2-propanol and tert-ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, tetrahydrofuran, and 1,4-dioxane.
- alcohols such as methanol, ethanol, 2-propanol and tert-ethanol
- aromatic hydrocarbons such as benzene, toluene and xylene, tetrahydrofuran, and 1,4-dioxane.
- One tellers can be used.
- polymerization initiator examples include azo compounds such as 2,2′-azobis (isobutyronitrile) and dimethyl 2,2′-azobis (2-methylpropionate), benzoyl peroxide, and tert-butyl peroxide.
- Peroxides, ferrous hydrogen peroxide ferrous salts, redox initiators such as benzoyl peroxide / dimethylaniline, and metal alky
- the copolymer When tert-butoxystyrene is used as the raw material monomer, the copolymer is dissolved in a hydrophilic solvent and heated under acidic conditions to hydrolyze the tert-butoxy group in the copolymer to hydroxyl groups.
- it may be a copolymer of at least one system selected from hydroxystyrene / 3-hydroxy-1-adamantyl acrylate and 3,5-dihydroxy-1-adamantyl (meth) acrylate.
- at least one copolymer selected from hydroxystyrene Z 3-hydroxy-11-adamantyl acrylate and 3,5-dihydroxy-11-adamantyl (meth) acrylate has an acid-labile group.
- an operation according to a usual protective group introduction reaction may be performed.
- an acetal group represented by the formula (III) is introduced, the raw material copolymer is dissolved in a solvent, and the unsaturated ether represented by the formula (Ilia) is dissolved in the presence of an acidic catalyst.
- an acidic catalyst By reacting the compound, a part of the hydroxyl group in the copolymer can be changed to an acetal group represented by the above formula (I11).
- the acidic catalyst used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as p-toluenesulfonic acid and hydrogensulfonic acid.
- the resin components constituting the positive resist composition of the present invention include polymerized units of hydroxystyrene, polymerized units of 3-hydroxy-1-adamantyl acrylate, and 3,5-dihydroxy (meth) acrylate. At least one polymer unit selected from polymer units of 1-adamantyl and a polymer having an acid-labile group. It is essential to have a combined unit, but it may contain other polymerized units such as styrene, acrylonitrile, methyl methacrylate, and methyl acrylate.
- hydrogenation may be partially carried out, or an alkyl group or an alkoxy group may be introduced into the phenol nucleus as long as it is soluble in an alkali.
- at least one polymerization unit selected from a polymerization unit of hydroxystyrene, a polymerization unit of 3-hydroxy-1-adamantyl acrylate, and a polymerization unit of 3,5-dihydroxy-11-adamantyl acrylate. It is advantageous to account for at least 50 mol% of the total resin.
- the ratio of both polymerized units is the mole of at least one polymerized unit selected from hydroxystyrene units: polymerized units of 3-hydroxy-1-adamantyl acrylate and polymerized units of 3,5-dihydroxy-1-adamantyl (meth) acrylate.
- the ratio is usually in the range of 99: 1 to 80:20, preferably in the range of 95: 5 to 85:15.
- the amount of the polymerized unit having an acid-labile group is usually 50 mol% or less, preferably 10 mol% or more, and 45 mol% or less.
- a copolymer for introducing an acid labile group into a copolymer of at least one selected from hydroxystyrene / 3-hydroxy-1-adamantyl acrylate and 3,5-dihydroxy-1-adamantyl acrylate When a compound, for example, di-tert-butyl dicarbonate or an unsaturated ether compound represented by the above formula (Ilia) is reacted, 3-hydroxy D xy 1-adamantyl acrylate and (meth) ) A protective group can also be introduced into at least one hydroxyl group selected from 3,5-dihydroxy-1-adamantyl acrylate.
- the acid generator which is another component of the positive resist composition, acts on the substance itself or the resist composition containing the substance by applying radiation such as light or electron beam to the substance.
- the substance is decomposed to generate an acid.
- the acid generated from the acid generator acts on the resin to cleave the acid-labile groups present in the resin. Will be done.
- Such acid generators include, for example, ionic salt compounds, s-triazine-based organic halogen compounds, sulfone compounds, sulfonate compounds and the like. Specifically, the following compounds can be mentioned.
- N- (10-camphorsulfonyloxy) naphthalimide N- (10-camphorsulfonyloxy) naphthalimide and the like.
- an organic base compound as a quencher
- an organic base compound it is preferable to mix a nitrogen-containing basic organic compound as a quencher.
- a nitrogen-containing basic organic compound include amines represented by the following formulas.
- RH, Ri 2 , R 13 , R 14 and R 15 independently represent hydrogen, alkyl, cycloalkyl, aryl or alkoxy which may be substituted by a hydroxyl group, and A is alkylene , Carbonyl or imino.
- R / C and alkoxy represented by R 11 to 15 may have about 1 to 6 carbon atoms
- cycloalkyl may have about 5 to 10 carbon atoms.
- the aryl may have about 6 to 10 carbon atoms.
- the alkylene represented by A may have about 1 to 6 carbon atoms, and may be linear or branched.
- a hindered amine compound having a hindered piperidine skeleton disclosed in Japanese Patent Application No. 9-208864 can also be used as a quencher.
- the resist composition of the present invention contains 80 to 99.8% by weight of a resin component and 0.1 to 20% by weight of an acid generator based on the total solid content therein. preferable.
- a nitrogen-containing basic organic compound as a quencher is contained, it is preferably used in a range of 10% by weight or less based on the total solid content in the resist composition.
- the composition may also contain small amounts of various additives such as sensitizers, dissolution inhibitors, other resins, surfactants, stabilizers, and dyes, if necessary.
- This resist composition is usually made into a resist solution in a state where the above-mentioned components are dissolved in a solvent, and applied to a substrate such as a silicon wafer by a conventional method such as spin coating.
- the solvent used here may be any one that dissolves each component, has an appropriate drying rate, and gives a uniform and smooth coating film after the solvent has evaporated, and is commonly used in this field. be able to.
- glycol ether esters such as ethyl acetate solv acetate, methyl acetate solv acetate and propylene glycol monomethyl ether acetate
- esters such as ethyl ethyl lactate, butyl acetate, amyl acetate and ethyl ethyl pyruvate, acetone, methyl butylolactone
- cyclic alcohols such as 3-methoxy-11-butanol.
- the resist film applied on the substrate and dried is subjected to an exposure treatment for patterning, followed by a heat treatment (PEB) to promote the deprotection group reaction, and then developed with an alkaline developer.
- PEB heat treatment
- alkaline developer used here can be any of various alkaline aqueous solutions used in this field, but generally, tetramethylammonium hydroxide or (2-hydroxyethyl) trimethylammonium hydroxide (commonly known as choline) is used. Aqueous solutions are often used.
- the weight average molecular weight (Mw) and the polydispersity (Mw Mn) are values measured by gel permeation and mouth chromatography using polystyrene as a standard.
- Synthetic Example 1 Production of hydroxystyrene / acrylic acid 3-hydroxy-1-adamantyl copolymer part 1 monoethoxylated product
- the obtained resin layer was dissolved in 634.7 g of methyl isobutyl ketone, 211.6 g of ion-exchanged water was added, stirred, and allowed to stand. Then, an organic layer portion was taken out. Further, stirring and liquid separation by adding 211.6 g of ion-exchanged water were repeated four times. This organic layer was distilled under reduced pressure at a temperature of 60 ° C. and a pressure of 80 Torr or less until the solution amount after distillation became 230.8 g, and was azeotropically dehydrated. A solution of 1-adamantyl copolymer in methyl isobutyl ketone was obtained.
- this resin is a resin in which hydroxyl groups in a copolymer of 4-hydroxystyrene and 3-hydroxy-1-adamantyl acrylate are partially converted into 11-ethoxyethyl esters.
- This resin is referred to as resin A.
- Synthesis Example 2 Another part of hydroxystyrene Z-acrylic acid 3-hydroxy-1-adamantyl copolymer 1 Production of monoethoxylated product
- Styrene (trade name "VP-15000") 40 g (333 mmol as p-hydroxystyrene unit) and p-toluenesulfonic acid monohydrate 47 mg (0.25 mmol) Dissolved in 720 g of propylene glycol monomethyl ether acetate. This solution was distilled under reduced pressure at a temperature of 60 ° C. and a pressure of 1 O Torr or less, and azeotropically dehydrated. The solution after distillation was 337 g.
- Example 1 resin ⁇ was used.
- Example 2 resin ⁇ and resin ⁇ were mixed in a 1: 1 ratio in terms of solid content.
- Comparative Example resin C was used.
- Each of these resins was mixed with an acid generator, quencher and a solvent in the following composition and dissolved, and then filtered through a fluororesin filter having a pore diameter of 0.2 m to prepare a resist solution.
- Solvent amount includes the amount brought in from the resin solution.
- PEB was performed on a hot plate under the conditions of 100 and 60 seconds, and paddle development was performed with a 2.38% aqueous solution of tetramethylammonium hydroxide. Observation, sensitivity, exposure latitude and resolution were examined as follows, and the results are shown in Table 1.
- Film loss sensitivity The minimum exposure required for the film to pass through the open field at one angle is displayed. This is Eth.
- Effective sensitivity Displayed at an exposure amount where a 0.25 m line and space pattern becomes 1: 1. This is Eo.
- Exposure margin Shown by the value of Eo / Eth. The larger this value is, the larger the range from the exposure amount at which the resist comes out of the film to the standard exposure amount is, and it is difficult for the resist to come off poorly. Therefore, it means that the exposure margin is excellent.
- a resist composition using a poly (hydroxystyrene Z at least one selected from 3-hydroxy-1-adamantyl acrylate and 3,5-dihydroxy-1-adamantyl acrylate) -based resin Exposure margin and resolution are improved.
- various performances such as sensitivity, heat resistance, remaining film ratio, coating property, and dry etching resistance can be maintained well. Therefore, by using this composition, a fine resist pattern can be accurately formed.
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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KR1020027012717A KR100750077B1 (ko) | 2000-03-28 | 2001-03-21 | 화학 증폭형 포지티브형 내식막 조성물 |
US10/239,896 US6846609B2 (en) | 2000-03-28 | 2001-03-21 | Chemical amplification type positive resist composition |
AU42740/01A AU4274001A (en) | 2000-03-28 | 2001-03-21 | Chemical amplification type positive resist composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2000/0088788 | 2000-03-28 | ||
JP2000088788A JP4329214B2 (ja) | 2000-03-28 | 2000-03-28 | 化学増幅型ポジ型レジスト組成物 |
Publications (1)
Publication Number | Publication Date |
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WO2001073512A1 true WO2001073512A1 (fr) | 2001-10-04 |
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ID=18604616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2001/002246 WO2001073512A1 (fr) | 2000-03-28 | 2001-03-21 | Composition de resist positif du type a amplification chimique |
Country Status (6)
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US (1) | US6846609B2 (ja) |
JP (1) | JP4329214B2 (ja) |
KR (1) | KR100750077B1 (ja) |
AU (1) | AU4274001A (ja) |
TW (1) | TWI243286B (ja) |
WO (1) | WO2001073512A1 (ja) |
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WO2004059392A1 (ja) * | 2002-12-26 | 2004-07-15 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型レジスト組成物およびレジストパターン形成方法 |
WO2004097526A1 (ja) * | 2003-04-30 | 2004-11-11 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型ホトレジスト組成物およびレジストパターン形成方法 |
US6846609B2 (en) | 2000-03-28 | 2005-01-25 | Sumitomo Chemical Company, Limited | Chemical amplification type positive resist composition |
WO2005026842A1 (ja) * | 2003-09-18 | 2005-03-24 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型レジスト組成物およびレジストパターンの形成方法 |
US7364831B2 (en) | 2004-05-12 | 2008-04-29 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and resist pattern formation method |
US7402372B2 (en) | 2003-06-13 | 2008-07-22 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method of forming resist pattern |
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JP4595275B2 (ja) * | 2001-09-28 | 2010-12-08 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
JP3895224B2 (ja) * | 2001-12-03 | 2007-03-22 | 東京応化工業株式会社 | ポジ型レジスト組成物及びそれを用いたレジストパターン形成方法 |
JP2005031233A (ja) * | 2003-07-09 | 2005-02-03 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、積層体、及びレジストパターン形成方法 |
KR100758870B1 (ko) * | 2003-09-25 | 2007-09-14 | 도오꾜오까고오교 가부시끼가이샤 | 저가속 전자선용 포지티브형 레지스트 조성물, 레지스트적층체 및 패턴 형성 방법 |
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JP2005350609A (ja) * | 2004-06-11 | 2005-12-22 | Daicel Chem Ind Ltd | 側鎖にアセタール構造を有する高分子化合物及びその製造法 |
JP4184352B2 (ja) * | 2005-03-04 | 2008-11-19 | 東京応化工業株式会社 | ポジ型レジスト組成物及びレジストパターン形成方法 |
JP4979915B2 (ja) * | 2005-09-09 | 2012-07-18 | 東京応化工業株式会社 | 高分子化合物、ネガ型レジスト組成物およびレジストパターン形成方法 |
JP5230400B2 (ja) * | 2008-12-19 | 2013-07-10 | 東京応化工業株式会社 | 樹脂の製造方法 |
KR101400131B1 (ko) * | 2013-02-22 | 2014-05-27 | 금호석유화학주식회사 | 레지스트용 중합체 및 이를 포함하는 레지스트 조성물 |
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WO2000046640A1 (fr) * | 1999-02-05 | 2000-08-10 | Sumitomo Chemical Company, Limited | Composition de resist positif de type a amplification chimique |
JP2001066778A (ja) * | 1999-08-27 | 2001-03-16 | Fujitsu Ltd | レジスト組成物及びレジストパターンの形成方法 |
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CN1190706C (zh) * | 1998-08-26 | 2005-02-23 | 住友化学工业株式会社 | 一种化学增强型正光刻胶组合物 |
JP4366766B2 (ja) * | 1999-04-30 | 2009-11-18 | 住友化学株式会社 | O−置換ビニルフェノール単位を有する重合体及びそれのレジストへの使用 |
JP4453138B2 (ja) * | 1999-12-22 | 2010-04-21 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
TW573225B (en) * | 2000-02-28 | 2004-01-21 | Sumitomo Chemical Co | Chemically amplified positive resist composition |
JP4329214B2 (ja) | 2000-03-28 | 2009-09-09 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
-
2000
- 2000-03-28 JP JP2000088788A patent/JP4329214B2/ja not_active Expired - Lifetime
-
2001
- 2001-03-21 US US10/239,896 patent/US6846609B2/en not_active Expired - Lifetime
- 2001-03-21 AU AU42740/01A patent/AU4274001A/en not_active Abandoned
- 2001-03-21 KR KR1020027012717A patent/KR100750077B1/ko active IP Right Grant
- 2001-03-21 WO PCT/JP2001/002246 patent/WO2001073512A1/ja active Application Filing
- 2001-03-23 TW TW090106941A patent/TWI243286B/zh not_active IP Right Cessation
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EP0789279A1 (en) * | 1996-02-09 | 1997-08-13 | Wako Pure Chemical Industries Ltd | Polymer and resist material |
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WO2000046640A1 (fr) * | 1999-02-05 | 2000-08-10 | Sumitomo Chemical Company, Limited | Composition de resist positif de type a amplification chimique |
JP2001066778A (ja) * | 1999-08-27 | 2001-03-16 | Fujitsu Ltd | レジスト組成物及びレジストパターンの形成方法 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6846609B2 (en) | 2000-03-28 | 2005-01-25 | Sumitomo Chemical Company, Limited | Chemical amplification type positive resist composition |
WO2004059392A1 (ja) * | 2002-12-26 | 2004-07-15 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型レジスト組成物およびレジストパターン形成方法 |
US7666569B2 (en) | 2002-12-26 | 2010-02-23 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method for forming resist pattern |
WO2004097526A1 (ja) * | 2003-04-30 | 2004-11-11 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型ホトレジスト組成物およびレジストパターン形成方法 |
KR100820499B1 (ko) * | 2003-04-30 | 2008-04-10 | 도쿄 오카 고교 가부시키가이샤 | 포지티브형 포토레지스트 조성물 및 레지스트 패턴 형성방법 |
US7449276B2 (en) | 2003-04-30 | 2008-11-11 | Tokyo Ohka Kogyo Co., Ltd. | Positive photoresist composition and method for forming resist pattern |
US7402372B2 (en) | 2003-06-13 | 2008-07-22 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method of forming resist pattern |
WO2005026842A1 (ja) * | 2003-09-18 | 2005-03-24 | Tokyo Ohka Kogyo Co., Ltd. | ポジ型レジスト組成物およびレジストパターンの形成方法 |
US7364831B2 (en) | 2004-05-12 | 2008-04-29 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and resist pattern formation method |
WO2015055891A1 (en) | 2013-10-16 | 2015-04-23 | Wärtsilä Finland Oy | Method for operating an internal combustion engine |
Also Published As
Publication number | Publication date |
---|---|
KR20030051418A (ko) | 2003-06-25 |
JP4329214B2 (ja) | 2009-09-09 |
US20030113661A1 (en) | 2003-06-19 |
US6846609B2 (en) | 2005-01-25 |
KR100750077B1 (ko) | 2007-08-21 |
JP2001272782A (ja) | 2001-10-05 |
AU4274001A (en) | 2001-10-08 |
TWI243286B (en) | 2005-11-11 |
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