KR20140120212A - Coating composition for forming fine pattern and method for forming fine pattern using the same - Google Patents

Coating composition for forming fine pattern and method for forming fine pattern using the same Download PDF

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KR20140120212A
KR20140120212A KR1020130036043A KR20130036043A KR20140120212A KR 20140120212 A KR20140120212 A KR 20140120212A KR 1020130036043 A KR1020130036043 A KR 1020130036043A KR 20130036043 A KR20130036043 A KR 20130036043A KR 20140120212 A KR20140120212 A KR 20140120212A
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formula
coating composition
fine pattern
acid
group
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KR1020130036043A
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Korean (ko)
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이정열
이형근
이재우
김재현
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주식회사 동진쎄미켐
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Priority to KR1020130036043A priority Critical patent/KR20140120212A/en
Priority to PCT/KR2014/002641 priority patent/WO2014163332A1/en
Priority to TW103112276A priority patent/TW201500852A/en
Publication of KR20140120212A publication Critical patent/KR20140120212A/en

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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
    • G03F7/26—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

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

Abstract

Disclosed are a coating composition for forming a fine pattern and a method for forming a fine pattern using the same, wherein the coating composition for forming a fine pattern forms a coating film on the surface of a photoresist pattern developed with a negative tone developer so as to reduce the line width or caliber of the pattern. The coating composition for forming a fine pattern includes a polymer compound represented by chemical formula 1 and an organic solvent. In chemical formula 1, R1 is a linear or branched hydrocarbon group of 1-20 carbon atoms with or without 1-3 oxygen atoms or a cyclic hydrocarbon group of 3-20 carbon atoms with or without 1-3 oxygen atoms; R2, R3 and R5 are respectively a hydrogen atom or a methyl group; X does not exist or is a hydrocarbon group of 1-3 carbons with or without 1-3 oxygen atoms; R4 is an end group of a polymer compound and is a hydrocarbon group of 1-10 carbon atoms with 1-5 nitrogen atoms; and a is a mole percent of a repetitive unit constituting a polymer, which is 100 mol% in chemical formula 1.

Description

[0001] The present invention relates to a coating composition for forming a fine pattern and a method for forming a fine pattern using the coating composition.

The present invention relates to a coating composition for forming a fine pattern, and more particularly, to a coating composition for forming a fine pattern capable of reducing a line width size or a diameter of a pattern by forming a coating film on the surface of a photoresist pattern formed using a negative tone developer Coating compositions and methods of forming fine patterns using the same.

As a method of forming a fine pattern, there is a need for development of an exposure apparatus or miniaturization of a pattern through introduction of an additional process (for example, pattern coating process) Reduction of the pattern space through) is most effective.

As a photoresist pattern forming method, there are a negative tone developing solution (NTD) and a positive tone developing solution (PTD, Positive Tone Development). The pattern forming method using the negative tone developing solution is to form a pattern by selectively dissolving and removing the non-exposed region with a negative tone developing solution. In the pattern forming method using the positive tone developing solution, by selectively dissolving and removing the exposed region with a positive tone developing solution To form a pattern. The method of forming a pattern using the negative tone developer can realize a reversed phase pattern even in a contact hole pattern or a trench pattern which is difficult to form due to insufficient exposure amount as compared with a pattern forming method using a positive tone developer, And an organic solvent is used as a developer for removing unexposed portions, so that a photoresist pattern can be formed more effectively.

As a method for refining the photoresist pattern through the introduction of the additional process, there is a pattern coating process for making the space portion of the formed photoresist pattern smaller, and a coating composition comprising a conventional commercialized water- To form a coating layer having a uniform thickness on the pattern, thereby forming a fine pattern. However, when the coating composition (conventional coating composition) containing the water-soluble polymer is coated on the developed photoresist pattern with a negative tone developer, the acidification ratio of the photoresist pattern (the deprotecting group of the photoresist pattern is the carboxyl group (-COOH) Is higher than that of the photoresist pattern developed with a conventional positive tone developer, the crosslinking reaction rate with the water-soluble polymer having a high polarity is increased, and the pattern is excessively fine. Therefore, in the case of a coating composition using a conventional water-soluble polymer, it is difficult to miniaturize the pattern and it is difficult to obtain a stable line width because the amount of change in the pattern line width (variation in the thickness of the coating film) The interface between the space portion and the pattern) is increased.

In addition, when the pH of the pattern coating composition using the conventional water-soluble polymer is more than 9, the photoresist pattern may be modified and melted by the basic material during the coating process of the coating composition, the etching resistance is low, and there is also a problem that CD (Critical Dimension, unit: nm) difference occurs in the trench pattern or the contact hole pattern space portion.

Accordingly, it is an object of the present invention to provide a method of forming a fine pattern using a coating film and a method of forming a pattern using the coating composition, And a method for forming a fine pattern using the coating composition.

In order to achieve the above object, the present invention provides a polymer compound represented by the following formula (1): And a coating composition for forming a fine pattern comprising an organic solvent.

[Chemical Formula 1]

Figure pat00001

In Formula 1, R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, which may or may not contain 1 to 3 oxygen atoms, or may be a linear or branched hydrocarbon group having 3 to 20 carbon atoms Each of R 2 , R 3 and R 5 is a hydrogen atom or a methyl group, X is a hydrocarbon group having 1 to 3 carbon atoms which does not contain or contains 1 to 3 oxygen atoms, R 4 is a hydrocarbon group having 1 to 10 carbon atoms containing 1 to 5 nitrogen atoms as a terminal of the polymer compound and a is a mole percentage of a repeating unit constituting the polymer and is 100 mol% in the above formula (1).

The present invention also provides a method of manufacturing a semiconductor device, comprising: forming a photoresist film on a semiconductor substrate on which an etching layer is formed; Exposing the photoresist film to light and developing it with a negative tone developer to form a photoresist pattern; Applying the coating composition for forming a fine pattern on the developed photoresist pattern; And heating and developing the photoresist pattern coated with the coating composition for fine pattern formation at 80 to 180 ° C to form a coating film.

The coating composition for forming a fine pattern according to the present invention comprises a liposoluble polymer compound containing nitrogen and an organic solvent and is produced 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 the defects (the phenomenon of melting of the pattern, the change of the pattern line width according to the temperature, the generation of foreign matter, and the like). In addition, since the coating composition of the present invention can maximize the difference in dissolution rate between the portion where the coating film is formed and the remaining portion which is removed in the developing process, compared with a conventional coating composition using a water-soluble polymer, (B), the pattern line width is varied in accordance with the temperature and the time in the bake process for forming a fine pattern, so that a more stable pattern line width can be realized in semiconductor production . Further, since the coating composition of the present invention uses an organic solvent (which can use the same developer as the negative tone developer) at the time of development after the formation of the coating film, the development equipment used in the pattern formation process is used without the need of installing an additional developing unit It is economical. In addition, the coating composition of the present invention has superior etching resistance as compared with the negative tone photoresist or the water-soluble polymer.

Hereinafter, the present invention will be described in detail.

The coating composition for forming a fine pattern according to the present invention is a polymer compound represented by the following formula (1) for reducing a pattern size (forming a fine pattern) by forming a coating film on a photoresist pattern formed using a negative tone developer. And organic solvents.

[Chemical Formula 1]

Figure pat00002

Wherein R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, preferably 2 to 15 carbon atoms, which may or may not contain 1 to 3 oxygen atoms, or may contain 1 to 3 oxygen atoms And R 2 , R 3 and R 5 are each a hydrogen atom or a methyl group, X is absent, or an oxygen atom having 1 to 3 carbon atoms And R 4 is a hydrocarbon group having 1 to 10 carbon atoms containing 1 to 5 nitrogen atoms as a terminal of the polymer compound and a is a repeating unit constituting the polymer In the above formula (1) is 100 mol%.

When R 1 is a linear or branched hydrocarbon having 1 to 20 carbon atoms, specific examples of R 1 include a methyl group, a methanol group (-CH 2 OH), an ethyl group, an ethanol group (-C 2 H 4 OH) Isopropyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tertiary butyl group, n-pentyl group, isopentyl group, Butyl group, normal heptane group, n-octane group, n-decane group and the like. When R 1 is a cyclic hydrocarbon group having 3 to 20 carbon atoms, R 1 is a monocyclic or polycyclic alkyl or alkenyl group having 3 to 20 carbon atoms, a cyclic ester group or a cyclic ether group having 3 to 15 carbon atoms, An aromatic group having 4 to 15 carbon atoms, and the like. Specific examples of the monocyclic or polycyclic alkyl or alkenyl group having 3 to 20 carbon atoms include a cyclohexyl group, an adamantane group, an octahydro-4,7-methano-indene group, a norbornene group and a dinobenzene group, Specific examples of the cyclic ester group or the cyclic ether group having 3 to 15 carbon atoms include dihydro-furan-2-one, tetrahydro-pyran-2-one, oxetane- [4.2.1.0 3,7] nonan-5-warmth, 4,8-dioxa-tricyclo [4.2.1.0 3,7] nonan-5-warmth, oxa-tricyclo [5.2.1.0 3,8 ] Decane-4-one, 5,9-dioxa-tricyclo [5.2.1.0 3,8 ] decane-4-one and 7-oxa-bicyclo [2.2.1] heptane group, Specific examples of the aromatic group include a phenyl group, a naphthalene group, and an anthracene group. As in the above example, R 1 may be substituted with a substituent such as a hydroxyl group (-OH), or may include an ether group (-O-). Specific examples of X include a carbonyl group (-CO-), an ester group (-COO-), an acetate group (-CH 2 COO-), and specific examples of R 4 include primary amines, Secondary amine, amide, amidine and the like, preferably amidine.

Representative examples of the polymeric compound represented by the formula (1) include the polymeric compounds represented by the following formulas (1a) to (1q).

[Formula 1a]

Figure pat00003

[Chemical Formula 1b]

Figure pat00004

[Chemical Formula 1c]

Figure pat00005

≪ RTI ID = 0.0 &

Figure pat00006

[Formula 1e]

Figure pat00007

(1f)

Figure pat00008

[Formula 1g]

Figure pat00009

[Chemical Formula 1h]

Figure pat00010

[Formula 1i]

Figure pat00011

[Chemical Formula 1j]

Figure pat00012

[Chemical Formula 1k]

Figure pat00013

≪ EMI ID =

Figure pat00014

[Formula 1m]

Figure pat00015

[Formula 1n]

Figure pat00016

≪ EMI ID =

Figure pat00017

[Chemical Formula 1p]

Figure pat00018

In the general formulas (1a) to (11), a represents a mole percentage of the repeating unit constituting the polymer, and represents 100 mol%. In the general formulas (1m) to (1p), a and b represent mole% , a is 0 to 100 mol%, preferably 1 to 99 mol%, more preferably 50 to 95 mol%, and b is 0 to 100 mol%, preferably 1 to 99 mol%, and preferably 5 To 50 mol%.

The weight average molecular weight of the polymer compound represented by Formula 1 is 2,000 to 100,000, preferably 3,000 to 50,000, and 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 coating performance (coating film formation becomes difficult) during coating, and if it exceeds 100,000, the solubility in an organic solvent may drop sharply. The pH of the polymer may be 7.0 to 8.5.

The polymer compound represented by Formula 1 is a brush-type oil-soluble polymer compound, which contains at least one nitrogen atom in the molecule and is heated to a high temperature (80 to 180 ° C) and developed with a negative tone developer A coating film can be formed on the surface of the pattern by crosslinking reaction with the photosensitive polymer on the pattern surface by the acid base reaction with the deprotected functional group on the surface of the photoresist pattern. That is, when a pattern reducing material (coating composition) composed of a polymer having nitrogen is applied to a photoresist pattern, a photoresist pattern and an upper coating film are crosslinked to form a mono layer in the photoresist pattern, A fine pattern with a reduced spacing of patterns is formed.

In the coating composition for forming a fine pattern according to the present invention, as the organic solvent, an organic solvent which does not deform the photoresist pattern developed with a negative tone developing solution when a coating film is formed using the coating composition may be used without limitation. As the organic solvent, a hydrocarbon compound having 2 to 12 carbon atoms containing 1 to 4 oxygen atoms can be used, and for example, a compound having 2 to 8 carbon atoms, preferably 4 to 8 carbon atoms, more preferably 6 to 8 carbon atoms, An ether compound having 2 to 12 carbon atoms, preferably 4 to 12 carbon atoms, more preferably 6 to 10 carbon atoms, an alcohol compound having 3 to 12 carbon atoms, preferably 4 to 12 carbon atoms, more preferably 6 to 12 carbon atoms, (For example, n-butyl acetate as a negative tone developer), and the like can be used. Specific examples of 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, di Isopentyl ether and the like, and specific examples of the ketone compound having 3 to 12 carbon atoms include methyl isobutyl ketone and the like. The above organic solvents may be used alone or in combination.

In the coating composition for forming a fine pattern according to the present invention, the content of the polymer compound represented by Formula 1 is 0.5 to 15% by weight, preferably 3 to 10% by weight, More preferably 3 to 8% by weight. If the content of the polymer compound is less than 0.5% by weight, the coating film may be difficult to form. If the content is more than 15% by weight, the uniformity of the coating film may be poor. The content of the organic solvent is the balance other than the polymer compound represented by the formula (1).

In the coating composition for forming a fine pattern according to the present invention, an acid catalyst, a surfactant, a basic compound and the like may be added. The acid catalyst used in the present invention is one capable of improving the degree of crosslinking or crosslinking of the film in the formation of a coating film and includes, for example, hydrochloric acid, sulfuric acid, phosphoric acid, methylsulfonic acid, ethylsulfonic acid, propylsulfonic acid, Examples of the organic acid include sulfonic acid, 2,4-dimethylbenzenesulfonic acid, ptoluenesulfonic acid (PTSA), camphorsulfonic acid, naphthylsulfonic acid, cyclohexylsulfonic acid, acetic acid, ethyl acetic acid, propyl acetic acid, isopropyl acetic acid, Can be used. When the acid catalyst is used, the content is 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the coating composition for forming fine patterns. When the amount is less than 0.1 parts by weight, There is a possibility that the effect of improving the rate may not be obtained. When the amount exceeds 5 parts by weight, there is a fear that the amount of crosslinking increases sharply due to excessive catalytic action due to excessive acid at the time of forming the coating film.

The surfactant used in the present invention is to increase the coating property such as the uniformly coated surface of the coating composition. Any conventional surfactant may be used. For example, depending on the size and thickness of the pattern, A surfactant, a cationic surfactant or an amphoteric surfactant may be used singly or in combination of two or more. More specific examples of the surfactant include alkylbenzenesulfonic acid salt surfactants, higher amine halides, quaternary ammonium salt surfactants, alkylpyridinium salt surfactants, amino acid surfactants and sulfonimide surfactants. have. The content of the surfactant when used is 0.01 to 5 parts by weight, preferably 0.1 to 1 part by weight, relative to 100 parts by weight of the coating composition for forming fine patterns. When the amount is less than 0.01 parts by weight, If the amount of the surfactant exceeds 5 parts by weight, the coating film quality may be deteriorated due to the foam generated by the surfactant during the formation of the coating film, or the loss of the photoresist pattern due to the excessive amount of the surfactant during the development of the coating film May occur.

The basic compound used in the present invention acts as a cross-linking agent and a stabilizer, and conventional amine compounds can be used. For example, triethanolamine (TEOA), 2-aminoethanol, 2 2- (2-aminoethoxy) ethanol, etc. may be used. The content of the basic compound is 0.01 to 2 parts by weight, preferably 0.05 to 1 part by weight, more preferably 0.1 to 0.5 parts by weight, relative to 100 parts by weight of the coating composition for forming fine patterns, If the amount is less than 2 parts by weight, there is a fear that the effect of the use of the basic compound may not be obtained. If the amount is more than 2 parts by weight, the basicity of the coating composition increases, and there is a possibility that the surface of the photoresist pattern is denatured during the formation of the coating film.

A method for forming a fine pattern of a semiconductor device using a coating composition according to the present invention includes the steps of: (a) forming a photoresist film on a semiconductor substrate on which a semiconductor layer is formed; (b) exposing the photoresist film to light using a predetermined exposure mask and an exposing device, and developing the photoresist film with a conventional negative tone developer such as n-butyl acetate to form a photoresist pattern; (c) applying the coating composition for forming a fine pattern on the developed photoresist pattern; (d) heating and developing the photoresist pattern coated with the coating composition for fine pattern formation at 80 to 180 DEG C to form a coating film.

The heating process in the step (d) is a step of forming a coating film by crosslinking the photosensitive polymer on the surface of the coated coating composition and the photoresist pattern. The heating temperature in the heating process is 80 to 180 ° C, preferably 110 to 150 ° C ° C., and the heating time is 5 to 300 seconds, preferably 50 to 90 seconds. If the heating temperature in the heating process is less than 80 ° C or the heating time is less than 5 seconds, a coating film (protective film) may not be formed on the photoresist pattern. If the heating temperature exceeds 180 ° C or the heating time is 300 seconds , There is a fear that the photoresist pattern is melted.

The method for forming a fine pattern of a semiconductor device includes applying a conventional coating film forming step using a coating composition according to the present invention to a photoresist pattern formed of a conventional negative tone developer, Unlike the case of using the apparatus, there is no need to install an additional developing unit, and the utilization rate of the apparatus can be increased.

Hereinafter, the present invention will be described in more detail with reference to specific examples. The following examples illustrate the present invention and are not intended to limit the scope of the present invention.

[Preparation Example 1] Preparation of polymeric compound represented by formula (1a)

(0.5 mol) of vinylbenzene (styrene), 11.7 g (0.05 mol) of 2,4-diphenyl-4-methyl-1-pentene as chain transfer agent and 2,2'- 0.5 g of azobis [2- (2-imidazolin-2-yl) propane] (VA-061, manufacturer: wako) was added and the reaction product was polymerized at 80 DEG C for 24 hours. , And the reaction product was washed three times with 150 mL of deionized water. The reaction product was slowly added dropwise to methanol and precipitated, and then dried in a dry oven to obtain 29.1 g of the oil-soluble polymer represented by Formula 1a (yield: 65% The weight average molecular weight (Mw) and polydispersity (PD) of the polymer synthesized by gel permeation chromatography (GPC) were analyzed (Mw = 9,250, PD = 1.45).

[Preparation Example 2] Preparation of polymeric compound represented by formula (1b)

(0.5 mol) of vinylbenzene, 11.7 g (0.05 mol) of 2,4-diphenyl-4-methyl-1-pentene as a chain transfer agent, and 2, 2-amidinopropane ) Dihydrochloride was added and the reaction product was polymerized for 24 hours at 80 DEG C. After completion of the polymerization reaction, the reaction was washed three times with 150 mL of deionized water. The reaction product was slowly added dropwise to methanol, (Yield: 58%). The weight average molecular weight (Mw) and the polydispersity (Mw) of the polymer synthesized by GPC (Gel Permeation Chromatography) (PD: Polydispersity) was analyzed (Mw = 7,500, PD = 1.37).

[Preparation Example 3] Preparation of polymeric compound represented by formula (1c)

(0.5 mol) of vinylbenzene and 11.7 g (0.05 mol) of 2,4-diphenyl-4-methyl-1-pentene as a chain transfer agent and 2,2'-azobis [N- 2-carboxyethyl) -2-methylpropionate] was added, and the reaction product was polymerized for 24 hours at 80 ° C. After the reaction was completed, the temperature of the reactor was lowered to 0 ° C., and 1.0 g And the reaction product was washed three times with 150 mL of deionized water. The reaction product was slowly added dropwise to methanol while being precipitated, and then dried in a dry oven to obtain the lipid- The weight average molecular weight (Mw) and polydispersity (PD) of the polymer synthesized by gel permeation chromatography (GPC) were analyzed (Mw = 6,230, PD = 1.44).

[Preparation Example 4] Preparation of a polymer compound represented by the formula (1d)

1d was obtained in the same manner as in Preparation Example 1, except that 103.0 g (0.5 mol) of adamantan-1-yl acrylate was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 1 (Yield: 77%, Mw = 10,640, PD = 1.51).

[Preparation Example 5] Preparation of polymeric compound represented by formula (1e)

Except that 103.0 g (0.5 mol) of adamantan-1-yl acrylate was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 2, (Yield: 62%, Mw = 9,410, PD = 1.45).

[Preparation Example 6] Preparation of a polymer compound represented by the formula (1f)

Except that 103.0 g (0.5 mol) of adamantan-1-yl acrylate was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 3, (Yield: 54%, Mw = 6,650, PD = 1.50).

[Preparation Example 7] Preparation of polymeric compound represented by formula (1g)

Except that 110.2 g (0.5 mol) of methacrylic acid tricyclo [5.2.1.02,6] decane-8-neil was used instead of 44.8 g (0.5 mol) of vinylbenzene in Production Example 1, (Yield: 68%, Mw = 9,950, PD = 1.44) was obtained in the same manner as in the synthesis of the oil-soluble polymer compound represented by Formula 1g.

[Preparation Example 8] Preparation of a polymer represented by the formula (1h)

Except that 110.2 g (0.5 mol) of methacrylic acid tricyclo [5.2.1.02,6] decane-8-neil was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 2, (Yield: 59%, Mw = 9,630, PD = 1.35) was obtained in the same manner as in the preparation of the oil-soluble polymer compound of Formula 1h.

[Preparation Example 9] Preparation of polymeric compound represented by formula ( 1)

Except that 110.2 g (0.5 mol) of methacrylic acid tricyclo [5.2.1.02,6] decane-8-neil was used instead of 44.8 g (0.5 mol) of vinylbenzene in Production Example 3, (Yield: 61%, Mw = 8,020, PD = 1.41) was obtained in the same manner as in the synthesis of the oil-soluble polymer represented by the formula (1i).

[Preparation Example 10] Preparation of a polymeric compound represented by the formula (1j)

Except that 110.0 g (0.5 mol) of adamantan-1-yl methacrylate was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 1, 57.2 g (yield: 52%, Mw = 8,910, PD = 1.49) of a fat-soluble polymer represented by 1j was obtained.

[Preparation Example 11] Preparation of polymeric compound represented by formula (1k)

(0.5 mol) of adamantyl methacrylate-1-yl ether was used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 2, (Yield: 55%, Mw = 7,840, PD = 1.48).

[Preparation Example 12] Preparation of polymeric compound represented by formula (11)

The same procedure as in Production Example 3 was conducted except that 110.0 g (0.5 mol) of adamantan-1-yl methacrylate was used instead of 44.8 g (0.5 mol) of vinylbenzene in Production Example 3, (Yield: 49%, Mw = 7,250, PD = 1.45).

[Preparation Example 13] Preparation of polymeric compound represented by formula (1m)

Except that 22.4 g (0.25 mol) of vinylbenzene and 55.0 g (0.25 mol) of adamantan-1-yl methacrylate were used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 1, (Yield: 52%, Mw = 9,110, PD = 1.44) was obtained in the same manner as in Production Example 1, with the proviso that the oil-soluble polymer represented by Formula 1m (a and b each independently 50 mol%) was obtained.

[Preparation Example 14] Preparation of polymeric compound represented by formula (1n)

Except that 22.4 g (0.25 mol) of vinylbenzene and 55.0 g (0.25 mol) of adamantan-1-yl methacrylate were used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 2, 37.1 g (yield: 48%, Mw = 8,590, PD = 1.46) of the oil-soluble polymer represented by the formula 1n (each independently a and b each having 50 mol%) were obtained in the same manner as in Production Example 2.

[Preparation Example 15] Preparation of polymeric compound represented by formula ( 10)

Except that 22.4 g (0.25 mol) of vinylbenzene and 55.0 g (0.25 mol) of adamantan-1-yl methacrylate were used in place of 44.8 g (0.5 mol) of vinylbenzene in Production Example 3, (Yield: 42%, Mw = 9,040, PD = 1.51) was obtained in the same manner as in Production Example 3, with the proviso that the oil-soluble polymeric compound represented by Formula 1o (a and b each independently 50 mol%) was obtained.

[Preparation Example 16] Preparation of polymeric compound represented by formula (1a)

Was prepared in the same manner as in Production Example 1, except that 0.25 g of the same material was used instead of 0.5 g of the 2,2'-azobis [2- (2-imidazolin-2-yl) propane] (Yield: 82%, Mw = 14,750, PD = 1.61).

[Preparation Example 17] Preparation of polymeric compound represented by formula (1a)

The same procedure as in Production Example 1 was carried out except that 1.0 g of the same material was used instead of 0.5 g of the 2,2'-azobis [2- (2-imidazolin-2-yl) propane] (Yield: 56%, Mw = 6,120, PD = 1.35). The yield of the oil-soluble polymer represented by Formula 1a was 25.1 g.

[Preparation Example 18] Preparation of a polymer represented by the formula (1p)

22.4 g (0.25 mol) of vinylbenzene and 55.0 g (0.25 mol) of methacrylic acid tricyclo [5.2.1.02,6] decane-8-neil were used in place of 44.8 g (0.5 mol) (Yield: 48%, Mw = 9,430, PD = 1.48 (m / z)) was obtained in the same manner as in Production Example 2, ).

[Examples 1-1 to 1-19 and Comparative Example 1] Preparation of coating composition for fine pattern formation

Soluble polymeric compounds of Production Examples 1 to 18 or water-soluble polymeric compounds of Formula 2 (a and b are 70 mol% and 30 mol%, respectively), oil-soluble and water-soluble surfactants, FC4430 Was completely dissolved in a solvent (n-butyl acetate (nBA) as the oil-soluble polymer compound and deionized water as the water-soluble polymer compound), followed by filtration through a 0.2 mu m disk filter to prepare a coating composition for forming a fine pattern.

(2)

Figure pat00019


 Polymer resin Surfactants menstruum Manufacturing example usage compound usage nba 2-heptanol Example 1-1 One 6.0g 94g - Examples 1-2 2 6.0g 94g - Example 1-3 3 6.0g 94g - Examples 1-4 4 6.0g 94g - Examples 1-5 5 6.0g 94g - Examples 1-6 6 6.0g 94g - Examples 1-7 7 6.0g 94g - Examples 1-8 8 6.0g 94g - Examples 1-9 9 6.0g 94g - Example 1-10 10 6.0g 94g - Example 1-11 11 6.0g 94g - Examples 1-12 12 6.0g 94g - Examples 1-13 13 6.0g 94g - Examples 1-14 14 6.0g 94g - Examples 1-15 15 6.0g 94g - Examples 1-16 16 6.0g 94g - Examples 1-17 17 6.0g 94g - Example 1-18 18 6.0g 94g - Example 1-19 7 6.0g 70g 24g Comparative Example 1 (2) 6.0g FC 4430 0.1 g Deionized water 91 g

[Examples 2-1 to 2-19 and Comparative Example 2] Fine pattern formation and evaluation

ArF organic anti-reflective coating composition DARC-A125 (manufacturer: Dongjin Semichem Co., Ltd.) was coated on a silicon wafer to a thickness of 33 nm and heated at 240 캜 for 60 seconds. Then, a negative photoresist composition DHA-HV100 Resist, manufacturer: Dongjin Semichem Co., Ltd.) was coated and heated at 95 캜 for 60 seconds (soft bake) to form a photoresist film. The wafer on which the photoresist film was formed was exposed using an ArF exposure apparatus (apparatus name: ASML 1200B, manufactured by ASML Corporation) having a numerical aperture of 0.85 and then heated at 110 ° C for 60 seconds to amplify the acid generated during exposure, (N-butyl acetate) for 15 seconds to form an elongated contact hole pattern having a line width of 74 nm and a Y-axis of 370 nm. Three pieces of each of the coating compositions prepared in Examples 1-1 to 1-19 and Comparative Example 1 were coated on the wafer having the contact hole pattern formed thereon and heated at 110 ° C, 130 ° C, and 150 ° C for 60 seconds, respectively And a negative tone developing solution (n-butyl acetate) for 15 seconds to develop a fine pattern in which the size (diameter) of the hole was shrunk (forming a coating film on the pattern). In the case of Comparative Example 2, it was immersed in deionized water (DI) for 60 seconds to be developed.
Composition for pattern coating Pattern before coating film formation
Diameter (nm) After the formation of the coating film, the pattern diameter (nm) Amount of change in pattern diameter at 150 占 폚 (nm) 110 ° C / 60s 130 ° C / 60s 150 ° C / 60s X axis Y axis X axis Y axis X axis Y axis X axis Y axis X axis Y axis Example 2-1 Example 1-1 74 370 62 356 61 353 59 353 15 17 Example 2-2 Examples 1-2 74 365 65 355 63 355 61 348 13 17 Example 2-3 Example 1-3 75 368 69 358 65 351 61 355 14 13 Examples 2-4 Examples 1-4 74 365 62 352 63 356 59 346 15 19 Example 2-5 Examples 1-5 74 365 62 356 63 355 61 350 13 15 Examples 2-6 Examples 1-6 76 364 68 352 63 353 63 342 13 22 Examples 2-7 Examples 1-7 74 369 63 355 64 350 62 356 12 13 Examples 2-8 Examples 1-8 72 368 64 359 65 354 62 352 10 16 Examples 2-9 Examples 1-9 75 368 65 352 68 350 66 355 9 13 Examples 2-10 Example 1-10 74 369 63 355 62 350 62 357 12 12 Examples 2-11 Example 1-11 76 368 64 357 63 352 63 354 13 14 Examples 2-12 Examples 1-12 74 365 62 359 66 359 61 350 13 15 Examples 2-13 Examples 1-13 74 365 63 354 64 358 62 351 12 14 Examples 2-14 Examples 1-14 75 365 66 351 62 352 63 349 12 16 Examples 2-15 Examples 1-15 78 364 66 352 65 355 65 345 13 19 Examples 2-16 Examples 1-16 74 358 64 343 66 343 61 344 13 14 Examples 2-17 Examples 1-17 75 371 58 356 56 353 56 345 19 26 Examples 2-18 Example 1-18 72 367 68 358 66 358 65 356 7 11 Example 2-19 Example 1-19 74 368 64 355 81 358 64 352 10 16 Comparative Example 2 Comparative Example 1 74 369 69 331 48 280 28 184 46 185

From Table 2, it can be seen that the coating composition for forming a fine pattern of the present invention is applied onto a photoresist pattern using a conventional negative tone developer, and is heated (baked) and developed to effectively reduce the diameter of the hole pattern And it can be seen that the rate of change of the diameter of the hole pattern according to the temperature is stable as compared with the water-soluble polymer coating composition (Comparative Example 1). Particularly, even in a contact hole pattern of a long shape rather than a circular shape, the amount of change in the X axis and the Y axis is constant.

[Examples 3-1 to 3-19 and Comparative Examples 3-1 and 3-2] Etching resistance of the coating composition for forming fine patterns

The coating compositions prepared in Examples 1-1 to 1-19 and Comparative Example 1 were coated on a silicon wafer to a thickness of 200 nm and heated at 110 DEG C for 60 seconds. The negative photoresist composition DHA-HV100 (ArF photoresist, manufacturer: Dongjin Semichem Co., Ltd.) used in Examples 2-1 to 2-19 and Comparative Example 2 was coated on a silicon wafer for comparison of etch resistance and reference setting And heated at 95 DEG C for 60 seconds (soft bake) to form a photoresist film. The wafer on which the photoresist film was formed was exposed using an ArF exposure machine (apparatus name: ASML 1200B, manufactured by ASML Co., Ltd.) having a numerical aperture of 0.85 and then heated at 110 ° C for 60 seconds to amplify the acid generated during exposure, A negative tone resist having a thickness of 200 nm was obtained. The wafer was dry-etched for 60 seconds under a condition of a gas ratio of O 2 : Cl 2 : Ar = 1: 4: 20 by using a dry etching equipment TCP-9600PTX (manufacturer: LAM) The ratio of the measured thickness is shown in Table 3 (the amount of change in etching of the photoresist was set to 1).

Fine pattern
Composition Initial thickness
(nm) Thickness after etching
(nm) Etching variation
(nm) Comparative Example 3-2 Preparation
Relative Etching Ratio Example 3-1 Example 1-1 200 174 26 0.23 Example 3-2 Examples 1-2 201 172 29 0.25 Example 3-3 Example 1-3 200 173 27 0.23 Example 3-4 Examples 1-4 203 168 35 0.30 Example 3-5 Examples 1-5 201 164 37 0.32 Examples 3-6 Examples 1-6 200 165 35 0.30 Examples 3-7 Examples 1-7 202 165 37 0.32 Examples 3-8 Examples 1-8 205 167 38 0.33 Examples 3-9 Examples 1-9 201 163 38 0.33 Examples 3-10 Example 1-10 201 167 34 0.30 Examples 3-11 Example 1-11 200 166 34 0.30 Examples 3-12 Examples 1-12 203 164 39 0.34 Examples 3-13 Examples 1-13 200 163 37 0.32 Examples 3-14 Examples 1-14 202 166 36 0.31 Examples 3-15 Examples 1-15 200 166 34 0.30 Examples 3-16 Examples 1-16 201 164 37 0.32 Examples 3-17 Examples 1-17 203 181 22 0.19 Examples 3-18 Example 1-18 202 173 29 0.25 Examples 3-19 Example 1-19 205 164 41 0.36 Comparative Example 3-1 Comparative Example 1 204 62 142 1.23 Comparative Example 3-2 Photoresist 201 86 115 1.00

From Table 3 above, it can be seen that the composition of the present invention also improved resistivity under dry etching conditions that were problematic in pattern shrinking materials and negative tone resists. Accordingly, when the coating composition for forming a fine pattern of the present invention is applied to a semiconductor production process requiring formation of a fine pattern, it is possible to reduce a diameter (line width (CD)) variation of a pattern according to temperature and also to have high etching resistance .

Claims (10)

A polymer compound represented by the following formula (1); And an organic solvent.
[Chemical Formula 1]
Figure pat00020

In Formula 1, R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, which may or may not contain 1 to 3 oxygen atoms, or may be a linear or branched hydrocarbon group having 3 to 20 carbon atoms Each of R 2 , R 3 and R 5 is a hydrogen atom or a methyl group, X is a hydrocarbon group having 1 to 3 carbon atoms which does not contain or contains 1 to 3 oxygen atoms, R 4 is a hydrocarbon group having 1 to 10 carbon atoms containing 1 to 5 nitrogen atoms as a terminal of the polymer compound and a is a mole percentage of a repeating unit constituting the polymer and is 100 mol% in the above formula (1). The coating composition for fine pattern formation according to claim 1, wherein the polymer compound represented by Formula 1 is selected from the group consisting of compounds represented by the following Formulas 1a to 1p.
[Formula 1a]
Figure pat00021

[Chemical Formula 1b]
Figure pat00022

[Chemical Formula 1c]
Figure pat00023

≪ RTI ID = 0.0 &
Figure pat00024

[Formula 1e]
Figure pat00025

(1f)
Figure pat00026

[Formula 1g]
Figure pat00027

[Chemical Formula 1h]
Figure pat00028

[Formula 1i]
Figure pat00029

[Chemical Formula 1j]
Figure pat00030

[Chemical Formula 1k]
Figure pat00031

≪ EMI ID =
Figure pat00032

[Formula 1m]
Figure pat00033

[Formula 1n]
Figure pat00034

≪ EMI ID =
Figure pat00035

[Chemical Formula 1p]
Figure pat00036

In the general formulas (1a) to (11), a represents a mole percentage of the repeating unit constituting the polymer, and represents 100 mol%. In the general formulas (1m) to (1p), a and b represent mole% , a is 0 to 100 mol%, and b is 0 to 100 mol%. The coating composition for fine pattern formation according to claim 1, wherein the polymer compound represented by Formula 1 has a weight average molecular weight of 2,000 to 100,000. The coating composition for fine pattern formation according to claim 1, wherein the organic solvent is a hydrocarbon compound having 2 to 12 carbon atoms containing 1 to 4 oxygen atoms. The organic solvent according to claim 4, wherein the organic solvent is selected from the group consisting of an alcohol compound having 2 to 8 carbon atoms, an ether compound having 2 to 12 carbon atoms, a ketone compound having 3 to 12 carbon atoms, an ester compound having 3 to 12 carbon atoms, ≪ / RTI > 5. The process of claim 4, wherein the organic solvent is selected from the group consisting of n-butyl acetate, n-hexanol, n-heptanol, diisopropyl ether, diisobutyl ether, diisopentyl ether, methyl isobutyl ketone, ≪ / RTI > [2] The coating composition for fine pattern formation according to claim 1, wherein the content of the polymer compound represented by Formula 1 is 0.5 to 15% by weight based on the coating composition for forming an entire fine pattern, and the remainder is an organic solvent. The method according to claim 1, wherein the coating composition for fine pattern formation comprises an additive selected from the group consisting of an acid catalyst, a surfactant, a basic compound, and a mixture thereof, 0.1 to 5 parts by weight based on 100 parts by weight of the coating composition and the content of the surfactant is 0.01 to 5 parts by weight based on 100 parts by weight of the entire coating composition for fine pattern formation, Is 0.01 to 2 parts by weight based on 100 parts by weight of the coating composition for forming a fine pattern. [Claim 9] The method according to claim 8, wherein the acid catalyst is at least one selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, methylsulfonic acid, ethylsulfonic acid, propylsulfonic acid, butylsulfonic acid, benzenesulfonic acid, 2,4-dimethylbenzenesulfonic acid, para- toluenesulfonic acid, camphorsulfonic acid, Is selected from the group consisting of cyclohexylsulfonic acid, acetic acid, ethyl acetic acid, propyl acetic acid, isopropyl acetic acid, and mixtures thereof. Forming a photoresist film on the semiconductor substrate on which the etching layer is formed;
Exposing the photoresist film to light and developing it with a negative tone developer to form a photoresist pattern;
Applying a coating composition for forming a fine pattern according to any one of claims 1 to 9 on the developed photoresist pattern; And
And heating and developing the photoresist pattern coated with the coating composition for fine pattern formation at 80 to 180 캜 to form a coating film.
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