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WO2014163332A1 - Composition de revêtement pour former un micromotif, et procédé pour former un micromotif au moyen de celle-ci - Google Patents

Composition de revêtement pour former un micromotif, et procédé pour former un micromotif au moyen de celle-ci Download PDF

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Publication number
WO2014163332A1
WO2014163332A1 PCT/KR2014/002641 KR2014002641W WO2014163332A1 WO 2014163332 A1 WO2014163332 A1 WO 2014163332A1 KR 2014002641 W KR2014002641 W KR 2014002641W WO 2014163332 A1 WO2014163332 A1 WO 2014163332A1
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WO
WIPO (PCT)
Prior art keywords
formula
forming
coating composition
micropattern
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2014/002641
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English (en)
Korean (ko)
Inventor
이정열
이형근
이재우
김재현
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Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
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Publication of WO2014163332A1 publication Critical patent/WO2014163332A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • 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
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • 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
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/325—Non-aqueous compositions

Definitions

  • the present invention relates to a coating composition for forming a micropattern, and more particularly, to forming a coating film on the surface of a photoresist pattern formed using a negative tone developer, for forming a micropattern which can reduce the line width size or aperture of the pattern. It relates to a coating composition and a method for forming a micropattern using the same.
  • pattern miniaturization for example, a pattern coating process
  • developing exposure equipment for example, introducing an additional process. Reduction of pattern space
  • a photoresist pattern forming method there is used a negative tone developer (NTD, Negative Tone Development) and a positive tone developer (PTD, Positive Tone Development).
  • NTD Negative Tone Development
  • PTD Positive Tone Development
  • the pattern forming method using the negative tone developer is to form a pattern by selectively dissolving and removing the non-exposed areas with a negative tone developer
  • the pattern forming method using the positive tone developer is by selectively dissolving and removing the exposure area with a positive tone developer To form a pattern.
  • the pattern forming method using the negative tone developer is implemented in reverse pattern even in contact hole patterns or trench patterns, which are difficult to form due to insufficient exposure, compared to the pattern forming method using the positive tone developer. Is easily formed, and an organic solvent is used as a developer for removing the unexposed portions, whereby a photoresist pattern can be formed more effectively.
  • a pattern coating process for making the space portion of the formed photoresist pattern even smaller, coating a coating composition containing a conventional commercially available water-soluble polymer to the pattern By forming a coating layer (coating layer) of a constant thickness on the pattern, to form a fine pattern.
  • the acidification ratio of the photoresist pattern (the deprotection group of the photoresist pattern is a carboxyl group (-COOH) (Conversion ratio) is higher than that of a photoresist pattern developed with a conventional positive tone developer, so that the crosslinking reaction rate with a highly polar water-soluble polymer becomes high and the pattern becomes excessively fine.
  • the amount of change of the pattern line width (change amount of the coating film thickness) according to the temperature is large, so that it is difficult to obtain a stable line width, and after forming the coating film, There is a problem that the incidence rate of foreign matter (scum) is increased, such as the interface between the space portion and the pattern.
  • an object of the present invention defects that occur when using a coating composition containing a water-soluble polymer in a photoresist pattern developed with a negative tone developer when forming a fine pattern using a coating film (pattern melting phenomenon, pattern line width according to temperature
  • the present invention provides a coating composition for forming a micropattern and a method of forming a micropattern using the same.
  • the present invention is a polymer compound represented by the formula (1); And it provides a coating composition for forming a micropattern comprising an organic solvent.
  • R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms containing or without 1 to 3 oxygen atoms, or having 3 to 20 carbon atoms containing or without 1 to 3 oxygen atoms Is a cyclic hydrocarbon group
  • R 2 , R 3 and R 5 are each a hydrogen atom or a methyl group
  • X is a hydrocarbon group of 1 to 3 carbon atoms which does not exist or contains 1 to 3 oxygen atoms or does not contain R
  • 4 is a terminal of the high molecular compound
  • a is a mole percent of the repeating unit constituting the polymer, 100 mole% in the formula (1).
  • the present invention also provides a method for forming a photoresist film on a semiconductor substrate on which an etched layer is formed; Developing the photoresist film with an exposure and negative tone developer to form a photoresist pattern; Applying the coating composition for forming the micropattern on the developed photoresist pattern; And heating and developing the photoresist pattern coated with the coating composition for forming a micropattern at 80 to 180 ° C., thereby forming a coating film.
  • the coating composition for forming a micropattern according to the present invention includes a fat-soluble high molecular compound and an organic solvent containing nitrogen, and occurs when a coating composition containing a water-soluble polymer is used in a photoresist pattern developed with a negative tone developer. It is possible to prevent defects (pattern melting, pattern line width change due to temperature, foreign matter generation, etc.).
  • the coating composition of the present invention can maximize the difference in the dissolution rate of the portion of the coating composition, the coating film formed and the remaining portion removed in the development process, compared to the conventional coating composition using a water-soluble polymer, It is effective for the implementation of patterns, and the variation of the pattern line width ( ⁇ CD (nm)) with temperature and time during the baking process to form a fine pattern is small, and thus more stable pattern line width can be realized in semiconductor production. .
  • the coating composition of the present invention uses an organic solvent (the same developer as the negative tone developer can be used) when developing after coating film formation, it is possible to use the developing equipment used in the pattern forming process without installing an additional developing unit. It is economical.
  • the coating composition of the present invention has superior etching resistance compared to negative tone photoresist or water-soluble polymer.
  • Coating composition for forming a micropattern according to the present invention is to form a coating film on the photoresist pattern formed using a negative tone developer, to reduce the pattern size (fine pattern formation), a polymer compound represented by the formula (1); And organic solvents.
  • R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, preferably 2 to 15 carbon atoms, or containing 1 to 3 oxygen atoms, or includes 1 to 3 oxygen atoms
  • a cyclic hydrocarbon group having 3 to 20 carbon atoms, preferably 4 to 15 carbon atoms, R 2 , R 3 and R 5 are each a hydrogen atom or a methyl group, and X is absent or 1 to 3 oxygen atoms Is a hydrocarbon group having 1 to 3 carbon atoms, or not containing
  • R 4 is a terminal of the polymer compound, a hydrocarbon group having 1 to 5 carbon atoms containing 1 to 5 nitrogen atoms, a is a repeating unit constituting the polymer As a mole percent of, in Formula 1 is 100 mol%.
  • R 1 is a linear or branched hydrocarbon having 1 to 20 carbon atoms
  • specific examples of R 1 may include a methyl group, a methanol group (-CH 2 OH), an ethyl group, an ethanol group (-C 2 H 4 OH), and a normal group.
  • Propyl group isopropyl group, normal butyl group, isobutyl group, tertiary butyl group, normal pentyl group, isopentyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2,3-dimethyl-2- Alkyl groups, such as a butyl group, normal heptane group, a normal octane group, and a normal decane group, can be illustrated.
  • R 1 is a cyclic hydrocarbon group having 3 to 20 carbon atoms
  • R 1 is a monocyclic or polycyclic alkyl group or alkene group having 3 to 20 carbon atoms, a cyclic ester group or cyclic ether group having 3 to 15 carbon atoms, It may be an aromatic group having 4 to 15 carbon atoms.
  • Specific examples of the C3-C20 monocyclic or polycyclic alkyl group or alken group include a cyclohexyl group, adamantane group, octahydro-4,7-methano-indene group, norbornene group, and dinorbornene group.
  • cyclic ester group or the cyclic ether group having 3 to 15 carbon atoms include a dihydro-furan-2-one group, a tetrahydro-pyran-2-one group, an oxetane-2-one group, and a 4-oxa-tricyclo [4.2.1.0 3,7 ] Nonan-5-warm, 4,8-dioxa-tricyclo [4.2.1.0 3,7 ] Nonan-5-warm, 5-oxa-tricyclo [5.2.1.0 3,8 ] Decane-4-one group, 5,9-dioxa-tricyclo [5.2.1.0 3,8 ] decane-4-one group, 7-oxa-bicyclo [2.2.1] heptane group, the carbon number 4 to 15
  • the aromatic group include a phenyl group, a naphthalene group, an anthracene group and the like.
  • R 1 may be substituted with a substituent such as a hydroxyl group (-OH) or may include an ether group (-O-).
  • X may include a carbonyl group (-CO-), an ester group (-COO-), an acetate group (-CH 2 COO-), and the like
  • R 4 may include a primary amine, Secondary amines, amides, amidines and the like, and are preferably amidines.
  • Representative examples of the polymer compound represented by Formula 1 may include a polymer compound represented by Formulas 1a to 1q.
  • a represents a mole percent of the repeating units constituting the polymer, and represents 100 mol%.
  • a and b represent mol% of the repeating units constituting each polymer.
  • a is 0 to 100 mol%, preferably 1 to 99 mol%, more preferably 50 to 95 mol%
  • b is 0 to 100 mol%, preferably 1 to 99 mol%, preferably 5 To 50 mol%.
  • the weight average molecular weight of the polymer compound represented by Chemical Formula 1 is 2,000 to 100,000, preferably 3,000 to 50,000, more preferably 5,000 to 15,000. If the weight average molecular weight of the polymer compound is less than 2,000, there is a fear that the coating performance during coating (the coating film is difficult to form), and if it exceeds 100,000, there is a fear that the solubility in the organic solvent is sharply dropped.
  • the acidity (pH) of the polymer may be 7.0 to 8.5.
  • the polymer compound represented by Chemical Formula 1 is a brush type fat-soluble polymer compound, which contains one or more nitrogen atoms in a molecule and is developed with a negative tone developer when heated to a high temperature (80 to 180 ° C.).
  • a deprotected functional group on the surface of the photoresist pattern and an acid base reaction the photoresist may be crosslinked with the photosensitive polymer to form a coating film on the surface of the pattern. That is, when a pattern reduction material (coating composition) made of a polymer having nitrogen is applied to the photoresist pattern, the photoresist pattern and the upper coating layer are crosslinked, and a mono layer is formed on the photoresist pattern, thereby forming a conventional photoresist. Fine patterns with reduced pattern spacing are formed.
  • an organic solvent which does not deform the photoresist pattern developed with a negative tone developer when forming a coating film using the coating composition may be used without limitation.
  • a hydrocarbon compound having 2 to 12 carbon atoms containing 1 to 4 oxygen atoms can be used, for example, 2 to 8 carbon atoms, preferably 4 to 8 carbon atoms, and more preferably 6 to 6 carbon atoms.
  • the alcohol compound having 2 to 8 carbon atoms include n-hexanol and n-heptanol
  • specific examples of the ether compound having 2 to 12 carbon atoms include diisopropyl ether, diisobutyl ether, and di Isopentyl ether, and the like
  • specific examples of the ketone compound having 3 to 12 carbon atoms include methyl isobutyl ketone and the like.
  • the compounds may be used alone or in combination.
  • the content of the polymer compound represented by Formula 1 is 0.5 to 15 wt%, preferably 3 to 10 wt%, based on the total micropattern forming coating composition, More preferably, it is 3-8 weight%. If the content of the high molecular compound is less than 0.5% by weight, there is a risk that the coating film formation is difficult, when the content of more than 15% by weight, there is a fear that the uniformity of the coating film. In addition, the content of the organic solvent, except the polymer compound represented by the formula (1).
  • an acid catalyst, a surfactant, a basic compound, or the like may be added.
  • the acid catalyst used in the present invention can improve the degree of crosslinking or crosslinking rate of the film during formation of the coating film, for example, hydrochloric acid, sulfuric acid, phosphoric acid, methyl sulfonic acid, ethyl sulfonic acid, propyl sulfonic acid, butyl sulfonic acid, benzene Sulfonic acid, 2,4-dimethylbenzene sulfonic acid, p-toluenesulfonic acid (PTSA), camphor sulfonic acid, naphthyl sulfonic acid, cyclohexyl sulfonic acid, acetic acid, ethyl acetate, propyl acetate, isopropyl acetic acid, mixtures thereof, and the like.
  • the content of the acid catalyst when used is 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, and less than 0.1 part by weight, based on 100 parts by weight of the coating composition for forming the entire micropattern. There is a fear that the effect of improving the rate may not be obtained, and if it exceeds 5 parts by weight, the amount of crosslinking may increase rapidly due to excessive catalysis caused by an excess of acid when forming the coating film.
  • Surfactant used in the present invention is to increase the coating property, such as the uniform coating surface of the coating composition, can be used a conventional surfactant, for example, depending on the size and thickness of the pattern, anion Surfactants, cationic surfactants or amphoteric surfactants may be used alone or in combination of two or more thereof. More specific examples of the surfactant may include alkylbenzene sulfonate-based surfactants, higher amine halides, quaternary ammonium salt-based surfactants, alkylpyridinium salt-based surfactants, amino acid-based surfactants, sulfonimide-based surfactants, and the like. have.
  • the content is 0.01 to 5 parts by weight, preferably 0.1 to 1 part by weight, and less than 0.01 part by weight, based on 100 parts by weight of the total micropattern-forming coating composition. If the content is more than 5 parts by weight, the coating film quality becomes poor due to the foam generated by the surfactant when forming the coating film, or the loss of the photoresist pattern by the excess surfactant in the process of developing the coating film. This may occur.
  • amine compounds for example, triethanolamine (TEOA), 2-aminoethanol, 2 2-aminoethoxyethanol (2- (2-aminoethoxy) ethanol) and the like can be used.
  • TEOA triethanolamine
  • 2-aminoethanol 2-aminoethoxyethanol
  • 2- (2-aminoethoxy) ethanol 2-aminoethoxyethanol
  • the content at the time of using the basic compound is 0.01 to 2 parts by weight, preferably 0.05 to 1 parts by weight, more preferably 0.1 to 0.5 parts by weight, and 0.01 parts by weight based on 100 parts by weight of the coating composition for forming the entire micropattern.
  • Method for forming a fine pattern of a semiconductor device using the coating composition according to the invention for example, (a) forming a photoresist film on a semiconductor substrate on which an etched layer is formed; (b) exposing the photoresist film using a predetermined exposure mask and an exposure machine, and developing with a conventional negative tone developer such as n-butyl acetate to form a photoresist pattern; (c) applying the coating composition for forming the micropattern on the developed photoresist pattern; (d) heating and developing the photoresist pattern coated with the coating composition for forming a micropattern at 80 to 180 ° C., thereby forming a coating film.
  • the heating process of step (d) is a step of forming a coating film by crosslinking the coated coating composition and the photosensitive polymer on the surface of the photoresist pattern, the heating temperature of the heating process is 80 to 180 °C, preferably 110 to 150 And heating time is 5 to 300 seconds, preferably 50 to 90 seconds. If the heating temperature of the heating process is less than 80 °C or the heating time is less than 5 seconds, there is a fear that a coating film (protective film) may not be formed on the photoresist pattern, the heating temperature exceeds 180 °C or the heating time is 300 seconds If it exceeds, there is a fear that the photoresist pattern is melted.
  • the method for forming a micropattern of the semiconductor device is to apply a conventional coating film forming step using the coating composition according to the present invention to a photoresist pattern formed of a conventional negative tone developer, a coating composition comprising a conventional water-soluble polymer Unlike in the case of using, there is no need to install additional developing units, etc., thereby increasing the utilization rate of the equipment.
  • the reaction mixture was slowly added dropwise and reacted for 1 hour, followed by washing the reaction product three times with 150 mL of deionized water.
  • the reactant was slowly added dropwise to methanol, followed by precipitation with a dry oven to dry the fat-soluble compound represented by Chemical Formula 1c. 21.5 g of a polymer compound was obtained (yield: 43%)
  • the fat-soluble high-molecular compound of Preparation Examples 1 to 18 or the water-soluble high-molecular compound of Formula 2 (a and b are 70 mol% and 30 mol%, respectively)
  • FC4430 of 3M is a fat-soluble and water-soluble surfactant This was completely dissolved in a solvent (lipophilic polymer compound is n-butyl acetate (nBA), water-soluble polymer compound is deionized water), and then filtered through a 0.2 ⁇ m disk filter to prepare a coating composition for forming a micropattern.
  • ArF organic anti-reflective coating composition DARC-A125 manufactured by Dongjin Semichem Co., Ltd.
  • the negative photoresist composition DHA-HV100 ArF photo A resist, a manufacturer: Dongjin Semichem Co., Ltd.
  • the wafer on which the photoresist film was formed was exposed using an ArF exposure machine (device name: ASML 1200B, manufacturer: ASML) having a numerical aperture of 0.85, and then heated at 110 ° C.
  • the coating composition for forming a micropattern of the present invention can be effectively applied on the photoresist pattern using a conventional negative tone developer, and thereby effectively reduce the diameter of the hole pattern by performing a heating (baking) and developing process. It can be seen that, compared with the water-soluble polymer coating composition (Comparative Example 1), it can be seen that the diameter change rate of the hole pattern with temperature is stable. In particular, the change amount of the X-axis and the Y-axis is constant even in a long contact hole pattern that is not circular.
  • the coating compositions prepared in Examples 1-1 to 1-19 and Comparative Example 1 were coated on a silicon wafer at a thickness of 200 nm and heated at 110 ° C. for 60 seconds.
  • the negative photoresist composition DHA-HV100 ArF photoresist, manufactured by Dongjin Semichem Co., Ltd.
  • Examples 2-1 to 2-19 and Comparative Example 2 was coated on a silicon wafer. And heated at 95 ° C. for 60 seconds (soft bake) to form a photoresist film.
  • the photoresist film formed wafer was exposed using an ArF exposure machine having a numerical aperture of 0.85 (device name: ASML 1200B, manufacturer: ASML), and then heated at 110 ° C. for 60 seconds to amplify the acid generated during exposure to deprotection. A negative tone resist of 200 nm in thickness was obtained.
  • the composition of the present invention also improved the resistance in dry etching conditions, which was a problem in the pattern reduction material or negative tone resist. Therefore, when the coating composition for forming a micropattern of the present invention is applied to a semiconductor production process requiring the formation of a micropattern, variation in the diameter (line width (CD)) of the pattern with temperature can be reduced, and high etching resistance is also achieved. .

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials For Photolithography (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Ceramic Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

La présente invention concerne : une composition de refroidissement pour former un micromotif capable de réduire la longueur de ligne ou le diamètre d'un motif par formation d'un film de revêtement sur la surface d'un motif de résine photosensible, qui est developpé par un révélateur de teinte négative ; et un procédé pour former un micromotif utilisant celle-ci. La composition de revêtement pour former un micromotif comprend : un composé polymère représenté par la formule chimique 1 dans la spécification ; et un solvant organique. Dans la formule chimique 1 dans la spécification, R1 est un groupe hydrocarboné linéaire ou ramifié en C1-20 contenant ou ne contenant pas 1 à 3 atomes d'oxygène ou un groupe hydrocarboné cyclique en C3-20 contenant ou ne contenant pas 1 à 3 atomes d'oxygène, R2, R3 et R5 sont chacun un atome d'hydrogène ou un groupe méthyle, X n'existe pas ou est un groupe hydrocarboné en C1-3 contenant ou ne contenant pas 1 à 3 atomes d'oxygène, R4, en tant que terminaison d'un composé polymère, est un groupe hydrocarboné en C1-10 contenant 1 à 5 atomes d'azote, et a, en tant que pourcentage en moles d'un motif de répétition constituant un polymère, est de 100 % en moles dans la formule chimique 1 dans la spécification.
PCT/KR2014/002641 2013-04-02 2014-03-28 Composition de revêtement pour former un micromotif, et procédé pour former un micromotif au moyen de celle-ci Ceased WO2014163332A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130036043A KR20140120212A (ko) 2013-04-02 2013-04-02 미세패턴 형성용 코팅 조성물 및 이를 이용한 미세패턴 형성방법
KR10-2013-0036043 2013-04-02

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WO2014163332A1 true WO2014163332A1 (fr) 2014-10-09

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KR (1) KR20140120212A (fr)
TW (1) TW201500852A (fr)
WO (1) WO2014163332A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9448483B2 (en) 2014-07-31 2016-09-20 Dow Global Technologies Llc Pattern shrink methods
US9665005B2 (en) 2015-06-03 2017-05-30 Dow Global Technologies Llc Pattern treatment methods
US9671697B2 (en) 2015-06-03 2017-06-06 Dow Global Technologies Llc Pattern treatment methods
US9684241B2 (en) 2015-06-03 2017-06-20 Dow Global Technologies Llc Compositions and methods for pattern treatment
US9703203B2 (en) 2015-06-03 2017-07-11 Dow Global Technologies Llc Compositions and methods for pattern treatment
US10162265B2 (en) 2015-12-09 2018-12-25 Rohm And Haas Electronic Materials Llc Pattern treatment methods

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6726449B2 (ja) * 2015-08-28 2020-07-22 東京応化工業株式会社 レジストパターン形成方法、シュリンク剤組成物及びシュリンク剤組成物の製造方法
US9696625B2 (en) * 2014-10-17 2017-07-04 Tokyo Ohka Kogyo Co., Ltd. Method of forming resist pattern
JP2016180842A (ja) * 2015-03-24 2016-10-13 東京応化工業株式会社 レジストパターン形成方法及びシュリンク剤組成物
JP6503206B2 (ja) 2015-03-19 2019-04-17 東京応化工業株式会社 レジストパターン修復方法
JP6877932B2 (ja) * 2015-09-28 2021-05-26 東京応化工業株式会社 レジストパターン形成方法及びシュリンク剤組成物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100354871B1 (ko) * 1997-12-31 2003-03-10 주식회사 하이닉스반도체 공중합체수지와그제조방법및이수지를이용한포토레지스트
KR20080037535A (ko) * 2006-10-25 2008-04-30 신에쓰 가가꾸 고교 가부시끼가이샤 질소 함유 유기 화합물, 레지스트 재료 및 패턴 형성 방법
KR20090024246A (ko) * 2006-06-27 2009-03-06 제이에스알 가부시끼가이샤 패턴 형성 방법 및 그것에 이용하는 유기 박막 형성용 조성물
US20090075002A1 (en) * 2007-09-14 2009-03-19 Korea Advanced Institute Of Science And Technology Block copolymer nanostructure formed on surface pattern with shape different from nanostructure of the block copolymer and method for preparation thereof
US20090092924A1 (en) * 2005-07-22 2009-04-09 Tokyo Ohka Kogyo Co., Ltd. Method of producing positive resist composition, positive resist composition, and method of forming resist pattern

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100354871B1 (ko) * 1997-12-31 2003-03-10 주식회사 하이닉스반도체 공중합체수지와그제조방법및이수지를이용한포토레지스트
US20090092924A1 (en) * 2005-07-22 2009-04-09 Tokyo Ohka Kogyo Co., Ltd. Method of producing positive resist composition, positive resist composition, and method of forming resist pattern
KR20090024246A (ko) * 2006-06-27 2009-03-06 제이에스알 가부시끼가이샤 패턴 형성 방법 및 그것에 이용하는 유기 박막 형성용 조성물
KR20080037535A (ko) * 2006-10-25 2008-04-30 신에쓰 가가꾸 고교 가부시끼가이샤 질소 함유 유기 화합물, 레지스트 재료 및 패턴 형성 방법
US20090075002A1 (en) * 2007-09-14 2009-03-19 Korea Advanced Institute Of Science And Technology Block copolymer nanostructure formed on surface pattern with shape different from nanostructure of the block copolymer and method for preparation thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9448483B2 (en) 2014-07-31 2016-09-20 Dow Global Technologies Llc Pattern shrink methods
US9665005B2 (en) 2015-06-03 2017-05-30 Dow Global Technologies Llc Pattern treatment methods
US9671697B2 (en) 2015-06-03 2017-06-06 Dow Global Technologies Llc Pattern treatment methods
US9684241B2 (en) 2015-06-03 2017-06-20 Dow Global Technologies Llc Compositions and methods for pattern treatment
US9703203B2 (en) 2015-06-03 2017-07-11 Dow Global Technologies Llc Compositions and methods for pattern treatment
US10162265B2 (en) 2015-12-09 2018-12-25 Rohm And Haas Electronic Materials Llc Pattern treatment methods

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