WO2010010928A1 - コーティング組成物及びパターン形成方法 - Google Patents
コーティング組成物及びパターン形成方法 Download PDFInfo
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- WO2010010928A1 WO2010010928A1 PCT/JP2009/063202 JP2009063202W WO2010010928A1 WO 2010010928 A1 WO2010010928 A1 WO 2010010928A1 JP 2009063202 W JP2009063202 W JP 2009063202W WO 2010010928 A1 WO2010010928 A1 WO 2010010928A1
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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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
- G03F7/405—Treatment with inorganic or organometallic reagents after imagewise removal
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02211—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound being a silane, e.g. disilane, methylsilane or chlorosilane
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0334—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane
- H01L21/0337—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane characterised by the process involved to create the mask, e.g. lift-off masks, sidewalls, or to modify the mask, e.g. pre-treatment, post-treatment
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
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- H—ELECTRICITY
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
- H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
Definitions
- the present invention relates to a coating composition that is used in a lithography process in the process of manufacturing a semiconductor device and can form a film covering a resist pattern. Moreover, it is related with the usage method of the said coating composition.
- a short-wavelength light such as an ArF excimer laser (wavelength of about 193 nm) is employed as a light source for exposure to form a resist pattern.
- a resist pattern formed from a resist having a small film thickness may disappear when the film to be processed is dry-etched using the resist pattern as a mask.
- Patterning methods are known that do not require consideration of the problem of dry etching resistance of the resist pattern as described above (see, for example, Patent Documents 1 to 5). That is, a resist pattern having a shape obtained by inverting a desired pattern is formed, a film covering (filling) the resist pattern is formed by a coating method, and then a process of exposing the upper surface of the resist pattern is performed. The resist pattern is removed. Thereafter, the material to be processed is etched using the reverse pattern formed in this way (a pattern having a shape obtained by inverting the resist pattern) as a mask. In this specification, this series of patterning methods is referred to as “reversal patterning”.
- the resist pattern and the film covering the resist pattern are formed via a lower layer resist, a film to be processed, or an underlayer.
- a pattern having a shape obtained by inverting the resist pattern is transferred to the lower layer resist, the film to be processed, or the base layer.
- a silicon-containing polymer is used as a material for the film covering the resist pattern.
- a silicon-containing polymer is known (see, for example, Patent Document 6).
- Patent Document 6 describes a polysilane that has excellent solubility in a solvent (toluene, propylene glycol monomethyl ether acetate) and can be suitably used as a coating solution (coating agent).
- Patent Documents 7 and 8 disclose a so-called sidewall method. That is, a sidewall having a predetermined width is formed on the side surface of the photoresist pattern, and then the photoresist pattern is removed. As a result, a fine pattern formed by the sidewall is obtained.
- the sidewall is coated with a photoresist pattern to form a silicon-containing polymer layer, and then exposed and baked to form a cross-linking layer at the interface between the photoresist pattern and the silicon-containing polymer layer, etc. It is formed through a process.
- this silicon-containing polymer those having an epoxy group as a crosslinkable functional group have been proposed, and further, those having a polysiloxane compound or a polysilsesquioxane compound have been proposed.
- JP 7-135140 A Japanese Patent No. 3848070 Japanese Patent No. 3697426 US Pat. No. 6,567,761 US Patent Application Publication No. 2007/0037410 JP 2007-77198 A JP 2008-72101A JP 2008-72097 A
- the present invention is applied to “reversal patterning” and an object thereof is to obtain a coating composition suitable for forming a film covering a resist pattern.
- a coating composition suitable for forming a film covering a resist pattern.
- the resist pattern is filled and that it is easy to apply uniformly on the substrate and that the mixing with the resist pattern is small.
- the coating film to be formed is used as a mask, it is desired that the etching rate is lower than that of the material to be processed, but it is not always necessary to have antireflection ability.
- Patent Document 6 cannot be said to describe whether or not a coating solution using polysilane is suitable for “reversal patterning”, in particular, whether the coating performance on a resist pattern is good or bad.
- the silicon-containing polymer layers described in Patent Document 7 and Patent Document 8 may be suitable for forming a cross-linked layer in the above-described sidewall method, but are not necessarily suitable for “reversal patterning”. It could not be said that it was a material.
- the first aspect of the present invention is an organopolysiloxane, the following formula (1a), formula (1b) or formula (1c): [Wherein, A 1 represents a hydrogen atom, a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms, or an acetyl group, A 2 represents a hydrogen atom, a methyl group or an acetyl group, A 3 represents a linear or branched divalent hydrocarbon group having 2 to 4 carbon atoms, A 4 represents a linear, branched or cyclic hydrocarbon group having 3 to 6 carbon atoms, A 5 represents a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms, and n represents 1 or 2. ] A lithographic coating composition for forming a film covering a resist pattern, comprising a solvent comprising an organic solvent as a main component and a quaternary ammonium salt or quaternary phosphonium salt.
- the second aspect of the present invention is polysilane, the following formula (1a), formula (1b) or formula (1c): [Wherein, A 1 represents a hydrogen atom, a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms, or an acetyl group, A 2 represents a hydrogen atom, a methyl group or an acetyl group, A 3 represents a linear or branched divalent hydrocarbon group having 2 to 4 carbon atoms, A 4 represents a linear, branched or cyclic hydrocarbon group having 3 to 6 carbon atoms, A 5 represents a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms, and n represents 1 or 2.
- a third aspect of the present invention is a method of forming a first resist pattern using an organic resist on a semiconductor substrate on which a layer to be processed is formed, and covering the first resist pattern according to the present invention.
- It is a pattern formation method including the process of exposing the upper part (part) of a pattern, and forming the pattern of the said coating film by removing a part or all of said 1st resist pattern.
- the layer to be processed is dry etched using the pattern of the coating film as a mask. Lines, contact holes, or trenches can be formed by this pattern forming method.
- an organic resist is used on the coating film.
- a step of forming a second resist pattern and a step of etching the coating film using the second resist pattern as a mask may be added.
- This pattern forming method corresponds to a double exposure process and is suitable for forming a fine pattern.
- the coating composition which concerns on the 1st aspect of this invention is excellent in the applicability
- the coating composition according to the first aspect of the present invention was fixed in a non-flowable state, that is, in a certain shape by baking at a relatively low temperature (80 ° C. to 150 ° C.) after coating with a resist pattern. Therefore, the film can be easily formed.
- the coating film thus obtained exhibits resistance to resist solvents such as propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether. Furthermore, the coating composition according to the first aspect of the present invention does not require a crosslinking agent, and the organopolysiloxane contained in the coating composition is not necessarily limited to those having an epoxy group.
- the coating composition according to the first aspect of the present invention includes an organopolysiloxane, a solvent containing a predetermined organic solvent as a main component, a quaternary ammonium salt or a quaternary phosphonium salt, and components added as necessary. (Organic acid, surfactant, etc.) are united to obtain characteristics suitable for application to the third aspect of the present invention.
- the coating composition which concerns on the 2nd aspect of this invention is excellent in the applicability
- the coating film thus obtained has improved resistance to resist solvents such as propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether. Even when a quaternary ammonium salt, a quaternary phosphonium salt, or a sulfonic acid compound is used instead of the crosslinking agent, the same effect as that when the crosslinking agent is included is exhibited. However, it should be noted that a composition containing an excess of a compound such as a quaternary ammonium salt, a quaternary phosphonium salt or a sulfonic acid may deteriorate the storage stability.
- the coating composition according to the second aspect of the present invention includes polysilane having no oxygen atom in the main chain, it is possible to increase the silicon content as compared with the case where polysiloxane is included. It can be expected to have high dry etching resistance against oxygen gas.
- the coating composition according to the second aspect of the present invention includes a terminal having a silanol group or a polysilane having a silanol group and a hydrogen atom, a solvent mainly containing a predetermined organic solvent, a crosslinking agent, a quaternary ammonium salt, At least one additive selected from the group consisting of a quaternary phosphonium salt and a sulfonic acid compound, and further components (organic acid, surfactant, etc.) added as necessary are integrated into the third aspect of the present invention.
- (A) is a figure which shows typically the cross section of the sample in which the resist pattern was formed in Example 11, and (B) is the image which image
- (A) is a figure which shows typically the cross section of the sample which formed the coating film in Example 11, and (B) is the image which image
- (A) is a figure which shows typically the cross section of the sample which exposed the upper part of the resist pattern by dry-etching a coating film in Example 11, and (B) diagonally upwards the cross section of this sample. It is the image image
- (A) is a figure which shows typically the cross section of the sample which removed the resist pattern and a part of resist underlayer film by dry etching in Example 11, and (B) is SEM from the diagonally upper direction of the cross section of this sample. It is an image taken with.
- (A) is a figure which shows typically the cross section of the sample in which the coating film was formed in Example 12
- (B) is the image which image
- (C ) Is an image of the sample taken by SEM from directly above the coating film.
- (A) is a figure which shows typically the cross section of the sample which exposed the upper part of the resist pattern by dry-etching a coating film in Example 12, (B) is the cross section of this sample from diagonally upward.
- (A) is a figure which shows typically the cross section of the sample which removed the resist pattern by dry etching in Example 12
- (B) is the image which image
- (C) is an image of the sample taken by SEM from directly above the resist pattern forming surface.
- the organopolysiloxane contained in the coating composition according to the first aspect of the present invention is, for example, the following formula (2): [Wherein, X represents a methyl group, an ethyl group, an alkenyl group having 2 to 3 carbon atoms, or a phenyl group, R 2 represents a methyl group or an ethyl group, and m represents 0 or 1. ]
- an acid such as hydrochloric acid, nitric acid, maleic acid or acetic acid can be used during the hydrolysis and / or during the condensation reaction.
- the product that is, the organopolysiloxane has a silanol group at its terminal.
- the silanol group may further have a methoxy group or an ethoxy group.
- the presence of silanol groups can be estimated by analyzing the coating composition according to the present invention using an FT-NIR (Fourier transform near infrared) spectrometer.
- Organopolysiloxane is a generic term for polymers having a main chain composed of siloxane bonds (structures in which Si and O are alternately connected) and having a hydrocarbon group in the side chain.
- formula (3) [Wherein, X is as defined in the above formula (2). ]
- the polymer or oligomer which has a unit structure represented by this is contained in organopolysiloxane.
- the main chain of the organopolysiloxane may be a cage type, a ladder type, a linear type, or a branched type.
- X in formula (3) is preferably a methyl group or an ethyl group.
- the polysilane contained in the coating composition according to the second aspect of the present invention is, for example, the following formula (4a) and / or the following formula (4b): [Wherein, each R 2 represents a methyl group, an ethyl group, an alkenyl group having 2 to 3 carbon atoms, or a phenyl group, and R 1 represents a hydrogen atom, a methyl group, or an ethyl group. ] It has at least 1 type of unit structure represented by these.
- the polysilane contained in the coating composition according to the second aspect of the present invention has a silanol group or a silanol group and a hydrogen atom at the terminal.
- the presence of a silanol group can be estimated by analyzing the composition using an FT-NIR (Fourier transform near infrared) spectrometer.
- Polysilane is a polymer having a main chain composed of Si—Si bonds.
- Specific examples of the unit structure represented by the formula (4a) and specific examples of the unit structure represented by the formula (4b) are shown below. However, the present invention is not limited to the specific examples shown in Formula (5) to Formula (16).
- R 2 in formula (4a) or formula (4b) is preferably a methyl group or an ethyl group
- R 1 in formula (4a) is preferably a hydrogen atom, a methyl group or an ethyl group.
- the main chain of the polysilane may be either linear or branched.
- the organic solvent represented by the formula (1a), formula (1b) or formula (1c) contained in the coating composition according to the first and second aspects of the present invention is the organic solvent. At a ratio of more than 50% by mass, preferably 60% by mass or more and 100% by mass or less.
- organic solvents include 4-methyl-2-pentanol, 1-butanol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, propylene glycol phenyl ether, dipropylene glycol n-propyl ether, and dipropylene glycol.
- Examples include n-butyl ether, dipropylene glycol dimethyl ether, tripropylene glycol methyl ether, propylene glycol diacetate, cyclohexanol acetate, and cyclohexanol. From these, an optimal organic solvent may be selected according to the type of organic resist used to form the resist pattern.
- Other solvent components include, for example, dipropylene glycol methyl ether, tripropylene glycol n-butyl ether, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, methyl acetate, ethyl acetate, isopropyl acetate, and n-propyl alcohol.
- the solvent needs to have little mixing with the resist pattern and good applicability to the substrate on which the resist pattern is formed.
- An organic solvent having a boiling point of 100 ° C. or less at 1 atm (101.3 kPa) is likely to volatilize at the time of application, and water has a high surface tension and is difficult to apply uniformly. The properties are not good. However, it is allowed to contain one or both of an organic solvent having a boiling point of 100 ° C. or less and water as a subcomponent of the solvent.
- the quaternary ammonium salt contained in the coating composition according to the first aspect of the present invention includes, for example, benzyltriethylammonium chloride, benzyltrimethylammonium chloride, benzyltributylammonium chloride, tetramethylammonium chloride, tetraethylammonium bromide, tetraethylammonium chloride, Examples include tetrapropylammonium bromide, tetrabutylammonium bromide, tributylmethylammonium chloride, trioctylmethylammonium chloride, and phenyltrimethylammonium chloride.
- the quaternary phosphonium salt contained in the coating composition according to the first aspect of the present invention includes, for example, ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, benzyltriphenylphosphonium chloride, butyltriphenylphosphonium bromide, tetrabutylphosphonium. Bromide. Since the quaternary ammonium salt and the quaternary phosphonium salt can promote the condensation of silanol groups present at the terminal of the organopolysiloxane, the curability of the coating composition according to the first aspect of the present invention is improved. I think that.
- examples of the quaternary ammonium salt include benzyltriethylammonium chloride, benzyltributylammonium chloride, benzyltributylammonium chloride, tetramethylammonium chloride, Examples include tetraethylammonium bromide, tetraethylammonium chloride, tetrapropylammonium bromide, tetrabutylammonium bromide, tributylmethylammonium chloride, trioctylmethylammonium chloride, and phenyltrimethylammonium chloride.
- the coating composition according to the second aspect of the present invention contains a quaternary phosphonium salt
- examples of the quaternary phosphonium salt include ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, benzyltriphenylphosphonium chloride, butyl.
- examples thereof include triphenylphosphonium bromide and tetrabutylphosphonium bromide. Since the quaternary ammonium salt and the quaternary phosphonium salt can promote the condensation of silanol groups present at the terminal of the polysilane, the curability of the coating composition according to the second aspect of the present invention is further improved. Conceivable. However, coexistence of a quaternary ammonium salt or a quaternary phosphonium salt and a sulfonic acid compound described later is not preferable for the coating composition according to the second aspect of the present invention.
- the crosslinking agent is a nitrogen-containing compound having 2 to 4 nitrogen atoms to which a methylol group or an alkoxymethyl group is bonded.
- a crosslinking agent include hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl) glycoluril, 1,3,4,6-tetrakis (hydroxymethyl) glycoluril, 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea and 1,1,3,3- Tetrakis (methoxymethyl) urea is mentioned.
- the coating composition according to the second aspect of the present invention contains a compound that promotes a crosslinking reaction (crosslinking catalyst)
- the crosslinking catalyst include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonic acid.
- sulfonic acid compounds such as camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid and pyridinium-1-naphthalenesulfonic acid.
- organic acid may be further added to the coating composition according to the first and second aspects of the present invention.
- organic acids include maleic acid, cis-5-norbornene-endo-2,3-dicarboxylic acid, cis-5-norbornene-exo-2,3-dicarboxylic acid, cis-1,2-cyclohexanedicarboxylic acid And cis-type dicarboxylic acids such as
- water may be added to the coating composition according to the first aspect of the present invention together with or in place of the organic acid.
- a surfactant may be further added to the coating composition according to the first and second aspects of the present invention.
- the surfactant can further improve the applicability of the coating composition to the substrate.
- a nonionic surfactant or a fluorosurfactant is used.
- the ratio of solid content with respect to the said composition is 1 to 30 mass%, for example.
- the ratio of the quaternary ammonium salt or the quaternary phosphonium salt to the solid content can be, for example, 0.001% by mass to 5% by mass.
- the ratio of the crosslinking agent to the solid content can be, for example, 0.1% by mass or more and 25% by mass or less, and the ratio of the crosslinking catalyst to the solid content can be, for example, 0.01% by mass or more and 5% by mass or less.
- the ratio of the organic acid with respect to solid content can be 0.1 mass% or more and 10 mass% or less, for example.
- the ratio of water with respect to solid content can be 5 mass% or less, or 3 mass% or less, for example.
- the coating composition according to the present invention is applied so as to cover a resist pattern formed on a semiconductor substrate, and the resist pattern is formed using an organic resist.
- This organic resist is either a positive resist or a negative resist, and a KrF excimer laser, an ArF excimer laser, EUV (extreme ultraviolet), or a chemically amplified resist that is sensitive to an electron beam can be used.
- organic resist is defined as not including a silicon-containing resist having a base polymer such as polysiloxane or polysilane.
- the resist pattern is preferably formed on the semiconductor substrate via a resist underlayer film in which one layer or two or more layers are laminated.
- the semiconductor substrate is typically a silicon wafer, but an SOI (Silicon on Insulator) substrate or a compound semiconductor wafer such as gallium arsenide (GaAs), indium phosphide (InP), or gallium phosphide (GaP) is used. May be.
- An insulating film such as a silicon oxide film, a nitrogen-containing silicon oxide film (SiON film), a carbon-containing silicon oxide film (SiOC film), or a fluorine-containing silicon oxide film (SiOF film) or a low-k film (low dielectric constant film)
- SiON film nitrogen-containing silicon oxide film
- SiOC film carbon-containing silicon oxide film
- SiOF film fluorine-containing silicon oxide film
- low-k film low dielectric constant film
- the average molecular weight of the polymer shown in the following synthesis examples of the present specification is a measurement result by gel permeation chromatography (hereinafter abbreviated as GPC).
- GPC device HLC-8220GPC (manufactured by Tosoh Corporation)
- GPC column Shodex [registered trademark] KF803L, KF802, KF801 (manufactured by Showa Denko KK) Column temperature: 40 ° C
- Solvent tetrahydrofuran (THF)
- Flow rate 1.0 ml / min Standard sample: Polystyrene (manufactured by Showa Denko KK)
- the average molecular weight of the obtained polymer by GPC was Mw 5500 in terms of standard polystyrene. In the present specification, “Mw” represents a weight average molecular weight.
- Example 1 To 25 g of the solution obtained in Synthesis Example 1, 0.01 g of benzyltriethylammonium chloride, 0.10 g of maleic acid, and 0.02 g of a surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) are added. Further, 4-methyl-2-pentanol is added to make a 4.0 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- a surfactant manufactured by DIC Corporation, trade name: Megafac R-30
- Example 2 To 25 g of the solution obtained in Synthesis Example 1, 0.02 g of benzyltriethylammonium chloride, 0.20 g of maleic acid, and 0.02 g of a surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) are added. Further, 4-methyl-2-pentanol was added to make a 4.0 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- a surfactant manufactured by DIC Corporation, trade name: Megafac R-30
- Example 3 To 25 g of the solution obtained in Synthesis Example 3, 0.01 g of benzyltriethylammonium chloride, 0.10 g of maleic acid, and 0.02 g of a surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) are added. Further, 4-methyl-2-pentanol was added to make a 4.0 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- a surfactant manufactured by DIC Corporation, trade name: Megafac R-30
- Example 4 To 25 g of the solution obtained in Synthesis Example 4, 0.01 g of benzyltriethylammonium chloride, 0.10 g of maleic acid, and 0.02 g of a surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) are added. Further, 4-methyl-2-pentanol was added to make a 4.0 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- a surfactant manufactured by DIC Corporation, trade name: Megafac R-30
- Example 5 Polysilane compound represented by the above formula (17) (produced by Osaka Gas Chemical Co., Ltd., weight average molecular weight 5900, number average molecular weight 1800, unit structure A and unit structure B are contained in proportions of 33 mol% and 64 mol%, respectively. And at least a silanol group at the end).
- Each R in the formula (17) independently represents a hydrogen atom, a methyl group, an ethyl group, an OH group or a phenyl group, and each X represents an OH group or an OH group and a hydrogen atom.
- Example 6 A polysilane compound used in Example 5 above was prepared and added to 165.0 g of a 4-methyl-2-pentanol solution containing the polysilane compound at a concentration of 20% by mass with a crosslinking agent (Nippon Cytec Industries, Ltd., trade name: POWDERLINK [ 1174) 4.16 g, surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) 0.21 g and p-toluenesulfonic acid 0.42 g were added, and 4-methyl-2- Pentanol is added to make a 4.0 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- a crosslinking agent Nippon Cytec Industries, Ltd., trade name: POWDERLINK [ 1174) 4.16 g, surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) 0.21 g and p-toluen
- Example 7 Polysilane compound represented by the formula (17) (Osaka Gas Chemical Co., Ltd., weight average molecular weight 5600, number average molecular weight 1900, unit structure A and unit structure B are contained in proportions of 10 mol% and 90 mol%, respectively. And at least a silanol group at the end).
- Each R independently represents a hydrogen atom, a methyl group, an ethyl group, an OH group or a phenyl group.
- each X of Formula (17) represents an OH group or an OH group and a hydrogen atom.
- Comparative Example 1 To 25 g of the solution obtained in Synthesis Example 1, 0.10 g of maleic acid and 0.02 g of a surfactant (manufactured by DIC Corporation, trade name: Megafac R-30) were added, and 4-methyl-2- Add pentanol to make a 4.0 wt% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.02 micrometer, and prepared the coating composition (solution).
- This comparative example differs from Example 1 in that neither a quaternary ammonium salt nor a quaternary phosphonium salt is used.
- Example 2 The polysilane compound used in Example 5 and Example 6 was prepared, and 4-methyl-2-pentanol was added thereto to form a 4.0 mass% solution, and then a polyethylene microfilter having a pore size of 0.02 ⁇ m was used. And filtered to prepare a coating composition (solution).
- This comparative example is different from Example 5 and Example 6 in that a crosslinking agent, a sulfonic acid compound and a surfactant are not used.
- Example 8 ⁇ Dry etching rate> A coating film formed using the coating compositions prepared in Examples 1 to 7 and Comparative Example 1, and an organic photoresist (trade name: PAR855, manufactured by Sumitomo Chemical Co., Ltd.) are used.
- the photoresist film was dry etched using CF 4 and O 2 as etching gases, and the dry etching rate was measured.
- the apparatus used for dry etching is RIE-10NR (manufactured by Samco Corp.). Table 1 shows the results of determining the ratio of the dry etching rate of the coating film to the dry etching rate of the photoresist film (coating film / photoresist film).
- Example 9 Solvent resistance> A sample in which a coating film was formed on a silicon wafer by spin-coating the coating composition prepared in Example 1 on a silicon wafer and then baking the silicon wafer at 150 ° C. or 205 ° C. for 60 seconds. was made.
- samples were prepared by the same method.
- Propylene glycol monomethyl ether acetate (hereinafter abbreviated as PGMEA) or propylene glycol monomethyl ether (hereinafter abbreviated as PGMEA) as a solvent was dropped on the coating film formed on each of the prepared samples and held for 60 seconds. . Thereafter, spin drying was performed for 30 seconds, followed by baking at 100 ° C. for 30 seconds to remove the solvent from the sample. The change in the thickness of the coating film on the silicon wafer was measured between before dropping the solvent and after removing the dropped solvent. The results are shown in Table 2.
- the coating composition prepared in Example 5 was spin-coated on a silicon wafer, and then the silicon wafer was baked at 150 ° C. for 60 seconds to prepare a sample in which a coating film was formed on the silicon wafer. .
- samples were prepared by the same method.
- PGMEA which is a solvent, was dropped on the coating film formed on each prepared sample and held for 60 seconds. Thereafter, spin drying was performed for 30 seconds, followed by baking at 100 ° C. for 30 seconds to remove the solvent from the sample. The change in the thickness of the coating film on the silicon wafer was measured between before dropping the solvent and after removing the dropped solvent. The results are shown in Table 3.
- Example 9 the coating film formed by baking at a relatively low temperature (150 ° C.) using the coating composition prepared in Examples 1 to 4 was prepared in Comparative Example 1. It can be seen that the film has a resistance to at least PGMEA and PGME as compared with a coating film formed by baking at the same temperature using the coating composition. In addition, the coating film formed by baking at a relatively low temperature (150 ° C.) using the coating composition prepared in Example 5 to Example 7 is the coating composition prepared in Comparative Example 2. It can be seen that the film is more resistant to PGMEA than the coating film formed by baking at the same temperature used.
- Example 10 ⁇ Step coverage and flatness>
- the coating film to be formed has high step coverage and flatness.
- coating test of the coating composition which concerns on this invention was done using the level
- the step substrate used was obtained from Advantech Co., Ltd., and the height of the step was 80 nm, the thickness of the coating film was 110 nm, the baking temperature and time were 110 ° C., and 60 seconds.
- FIGS. 1A, 1B, 1C, and 1D show images obtained by photographing the cross section of the stepped substrate before forming the coating film with a scanning electron microscope (hereinafter abbreviated as SEM). And the image which image
- SEM scanning electron microscope
- Example 11 ⁇ Application to “Reversal Patterning”>
- the resist underlayer film 102 is formed using a composition containing a crosslinking agent (trade name: POWDERLINK [registered trademark] 1174 manufactured by Nippon Cytec Industries, Ltd.) and pyridinium-p-toluenesulfonic acid.
- a crosslinking agent trade name: POWDERLINK [registered trademark] 1174 manufactured by Nippon Cytec Industries, Ltd.
- a resist pattern 103 was formed using an organic photoresist (trade name: PAR855, manufactured by Sumitomo Chemical Co., Ltd.) as shown in FIG.
- the coating composition prepared in Example 1 was spin-coated so as to cover the resist pattern 103, and baked at 110 ° C. for 60 seconds, thereby forming the coating film 104 as shown in FIG. Formed. Thereafter, dry etching using CF 4 as an etching gas was performed to expose the upper portion of the resist pattern 103 as shown in FIG. In FIG. 4A, the upper surface of the resist pattern 103 and the upper surface of the coating film 104 are drawn on the same plane. However, depending on dry etching conditions, the upper surface of the resist pattern 103 may be etched, resulting in a shape in which the upper surface of the resist pattern is slightly recessed from the upper surface of the coating film 104.
- FIG. 5A shows a case where at least a part of the resist underlayer film 102 is etched together with the resist pattern 103.
- FIG. 2B shows an image obtained by photographing the cross section of the sample corresponding to FIG.
- FIG. 3B shows an image obtained by photographing the cross section of the sample corresponding to FIG.
- FIG. 4B shows an image obtained by photographing the cross section of the sample corresponding to FIG.
- FIG. 5B shows an image obtained by photographing the cross section of the sample corresponding to FIG.
- FIG. 5B shows that a pattern having a shape obtained by inverting the resist pattern is formed.
- Example 12 the coating composition prepared in Example 5 was spin-coated so as to cover the resist pattern 103, and baked at 110 ° C. for 60 seconds, thereby forming the coating film 204 as shown in FIG. Formed. Thereafter, dry etching using CF 4 as an etching gas was performed to expose the upper portion of the resist pattern 103 as shown in FIG. Finally, dry etching using O 2 as an etching gas was performed, and the resist pattern 103 was removed as shown in FIG.
- 6B and 6C show images obtained by photographing the cross section and the upper surface of the sample corresponding to FIG. 6A, respectively, with an SEM.
- 7B and 7C show images obtained by photographing the cross section and the upper surface of the sample corresponding to FIG. 7A with an SEM, respectively.
- 8B and 8C show images obtained by photographing the cross section and the upper surface of the sample corresponding to FIG. 8A with an SEM, respectively.
- 8B and 8C show that a pattern having a shape obtained by inverting the resist pattern is formed.
Abstract
Description
で表される有機溶媒を主成分とする溶剤、及び第4級アンモニウム塩又は第4級ホスホニウム塩を含む、レジストパターンを被覆する膜を形成するための、リソグラフィー用コーティング組成物である。
で表される有機溶媒を主成分とする溶剤、及び架橋剤、第4級アンモニウム塩、第4級ホスホニウム塩及びスルホン酸化合物からなる群から選択される少なくとも1種を含み、前記ポリシランはその末端にシラノール基又は該シラノール基と水素原子を有する、レジストパターンを被覆する膜を形成するための、リソグラフィー用コーティング組成物である。
で表される1種又は2種以上の化合物の加水分解及び縮合反応により得られる生成物である。式(2)において、mが0の場合、テトラメトキシシラン又はテトラエトキシシランを示す。オルガノポリシロキサンを得るための原料化合物として、式(2)で表される化合物を2種以上用いることが好ましい。加水分解の際及び/又は縮合反応の際、塩酸、硝酸、マレイン酸又は酢酸などの酸を用いることができる。
で表される少なくとも1種の単位構造を有する。
GPC装置:HLC-8220GPC(東ソー(株)製)
GPCカラム:Shodex〔登録商標〕KF803L,KF802,KF801(昭和電工(株)製)
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:1.0ml/min
標準試料:ポリスチレン(昭和電工(株)製)
テトラエトキシシラン20.31g、フェニルトリメトキシシラン1.49g、メチルトリエトキシシラン8.02g及びエタノール33.34gを100mlのフラスコに入れて溶解させ、得られた混合溶液をマグネチックスターラーにて撹拌しながら加温し、還流させた。次にイオン交換水9.83gに塩酸0.03gを溶解させた水溶液を前記混合溶液に添加した。2時間反応させた後、得られた反応溶液を室温まで冷却した。その後、反応溶液に4-メチル-2-ペンタノール100gを加え、反応副生物であるメタノール及びエタノール、並びに水、塩酸を減圧留去し、加水分解縮合物溶液を得た。得られたポリマーのGPCによる平均分子量は、標準ポリスチレン換算でMw5500であった。なお、本明細書において“Mw”は重量平均分子量を表す。
テトラエトキシシラン76.76g、フェニルトリメトキシシラン8.12g及び4-メチル-2-ペンタノール84.88gを300mlのフラスコに入れて溶解させ、得られた混合溶液をマグネチックスターラーにて撹拌しながら加温し、100℃で反応させた。次にイオン交換水28.75gにマレイン酸1.49gを溶解させた水溶液を前記混合溶液に添加した。1時間反応させた後、得られた反応溶液を室温まで冷却した。その後、反応溶液にプロピレングリコールモノメチルエーテルアセテート200gを加え、反応副生物であるメタノール及びエタノール、並びに水を減圧留去し、加水分解縮合物溶液を得た。得られたポリマーのGPCによる平均分子量は、標準ポリスチレン換算でMw4500であった。
テトラエトキシシラン24.99g、メチルトリエトキシシラン9.16g及びエタノール35.86gをフラスコに入れて溶解させ、得られた混合溶液をマグネチックスターラーにて撹拌しながら加温し、還流させた。次に0.01M塩酸水溶液12.04gを前記混合溶液に添加した。なお、本明細書において、“M”はmol/Lを表す。2時間反応させた後、得られた反応溶液を室温まで冷却した。その後、反応溶液に4-メチル-2-ペンタノール100gを加え、反応副生物であるメタノール及びエタノール、並びに水、塩酸を減圧留去し、加水分解縮合物溶液を得た。得られたポリマーのGPCによる平均分子量は、標準ポリスチレン換算でMw4800であった。
テトラエトキシシラン24.96g、メチルトリエトキシシラン6.11g、ビニルトリエトキシシラン2.54g及びエタノール33.65gをフラスコに入れて溶解させ、得られた混合溶液をマグネチックスターラーにて撹拌しながら加温し、還流させた。次に0.01M塩酸水溶液12.04gを前記混合溶液に添加した。2時間反応させた後、得られた反応溶液を室温まで冷却した。その後、反応溶液に4-メチル-2-ペンタノール100gを加え、反応副生物であるメタノール及びエタノール、並びに水、塩酸を減圧留去し、加水分解縮合物溶液を得た。得られたポリマーのGPCによる平均分子量は、標準ポリスチレン換算でMw4200であった。
合成例1にて得られた溶液25gに、ベンジルトリエチルアンモニウムクロリド0.01g、マレイン酸0.10g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.02gを加え、さらに4-メチル-2-ペンタノールを加え4.0質量%溶液とする。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
合成例1にて得られた溶液25gに、ベンジルトリエチルアンモニウムクロリド0.02g、マレイン酸0.20g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.02gを加え、さらに4-メチル-2-ペンタノールを加え4.0質量%溶液とした。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
合成例3にて得られた溶液25gに、ベンジルトリエチルアンモニウムクロリド0.01g、マレイン酸0.10g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.02gを加え、さらに4-メチル-2-ペンタノールを加え4.0質量%溶液とした。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
合成例4にて得られた溶液25gに、ベンジルトリエチルアンモニウムクロリド0.01g、マレイン酸0.10g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.02gを加え、さらに4-メチル-2-ペンタノールを加え4.0質量%溶液とした。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
上記実施例5で用いたポリシラン化合物を用意し、これを濃度20質量%で含む4-メチル-2-ペンタノール溶液165.0gに、架橋剤(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)4.16g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.21g及びp-トルエンスルホン酸0.42gを加え、さらに4-メチル-2-ペンタノールを加えて4.0質量%溶液とする。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
前記式(17)で表されるポリシラン化合物(大阪ガスケミカル(株)製、重量平均分子量5600、数平均分子量1900、単位構造A及び単位構造Bをそれぞれ10モル%、90モル%の割合で含有し、末端に少なくともシラノール基を有する。)を用意する。各Rはそれぞれ独立に水素原子、メチル基、エチル基、OH基又はフェニル基を表す。そして、式(17)の各Xは、OH基又はOH基と水素原子を表す。このポリシラン化合物を濃度20質量%で含む4-メチル-2-ペンタノール溶液165.0gに、架橋剤(日本サイテックインダストリーズ(株)、商品名:CYMEL〔登録商標〕303)4.16g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.21g及びp-トルエンスルホン酸0.42gを加え、4.0質量%溶液とした。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。
合成例1にて得られた溶液25gに、マレイン酸0.10g、界面活性剤(DIC(株)製、商品名:メガファックR-30)0.02gを加え、さらに4-メチル-2-ペンタノールを加え4.0質量%溶液とする。そして、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。本比較例は、第4級アンモニウム塩、第4級ホスホニウム塩のいずれも用いない点で、前記実施例1と異なる。
前記実施例5及び実施例6で用いたポリシラン化合物を用意し、これに4-メチル-2-ペンタノールを加え4.0質量%溶液とした後、孔径0.02μmのポリエチレン製ミクロフィルターを用いてろ過し、コーティング組成物(溶液)を調製した。本比較例は、架橋剤、スルホン酸化合物及び界面活性剤を用いない点で、前記実施例5及び実施例6と異なる。
<ドライエッチング速度>
実施例1乃至実施例7及び比較例1で調製されたコーティング組成物を用いて形成された被覆膜、及び有機フォトレジスト(住友化学(株)製、商品名:PAR855)を用いて形成されたフォトレジスト膜に対し、エッチングガスとしてCF4及びO2を使用してドライエッチングを行い、ドライエッチング速度を測定した。ドライエッチングに用いた装置はRIE-10NR(サムコ(株)製)である。そして、上記フォトレジスト膜のドライエッチング速度に対する上記被覆膜のドライエッチング速度の比(被覆膜/フォトレジスト膜)を求めた結果を表1に示す。
<溶剤耐性>
シリコンウエハー上に、実施例1で調製されたコーティング組成物をスピンコートし、次いでそのシリコンウエハーを150℃又は205℃で60秒間ベークすることにより、被覆膜がシリコンウエハー上に形成された試料を作製した。実施例2、実施例3、実施例4及び比較例1で調製されたコーティング組成物についても、同様の方法により試料を作製した。作製された各試料に形成されている被覆膜に、溶剤であるプロピレングリコールモノメチルエーテルアセテート(以下、PGMEAと略称)又はプロピレングリコールモノメチルエーテル(以下、PGMEと略称)を滴下し、60秒間保持した。その後、30秒間スピンドライを行い、さらに100℃で30秒間ベークし、試料から溶剤を除去した。溶剤を滴下する前と、滴下した溶剤を除去した後との間で、シリコンウエハー上の被覆膜の膜厚の変化を測定した。その結果を表2に示す。
<段差被覆性及び平坦性>
本発明に係るコーティング組成物を用いて、良好なコンタクトホールを得るためには、形成される被覆膜が、段差被覆性及び平坦性が高いことが必要となる。そこで、シリコン基板上に段差が形成された段差基板を用いて、本発明に係るコーティング組成物の塗布試験を行った。使用した段差基板は、(株)アドバンテックから入手したもので、段差の高さは80nm、被覆膜の厚さは110nm、ベーク温度及び時間は110℃,60秒である。孤立ラインのみを有する段差基板及びL/S(ラインアンドスペース)の異なる3種類の段差基板の合計4種類の段差基板を用い、実施例5で調製されたコーティング組成物をスピンコートし、上記の条件でベークして被覆膜を形成した。被覆膜を形成する前の段差基板の断面を走査型電子顕微鏡(以下、SEMと略称する)で撮影した像を図1(A)、(B)、(C)及び(D)に示し、並びに、被覆膜を形成した試料の断面をSEMで撮影した像を図1(a)、(b)、(c)及び(d)に示す。いずれの試料においても、段差基板の段差を十分に被覆できている。
<“リバーサルパターニング”への適用>
シリコンウエハー101上に、下記式(18a)、(18b)及び(18c):
で表される3種の単位構造を有する共重合体(重量平均分子量30000、単位構造(18a)、単位構造(18b)及び単位構造(18c)をそれぞれ34質量%、33質量%及び33質量%の比で含有する。)、架橋剤(日本サイテックインダストリーズ(株)製、商品名:POWDERLINK〔登録商標〕1174)及びピリジニウム-p-トルエンスルホン酸を含む組成物を用いてレジスト下層膜102を形成し、その上に、有機フォトレジスト(住友化学(株)製、商品名:PAR855)を用いて、図2(A)に示すようにレジストパターン103を形成した。ターゲットCD(Critical Dimension)は80nm、L/S(ラインアンドスペース)=80/100である。
次に、実施例5で調製されたコーティング組成物を、レジストパターン103を被覆するようにスピンコートし、110℃で60秒間ベークすることによって、図6(A)に示すように被覆膜204を形成した。その後、エッチングガスとしてCF4を用いたドライエッチングを行い、図7(A)に示すようにレジストパターン103の上部を露出させた。最後に、エッチングガスとしてO2を用いたドライエッチングを行い、図8(A)に示すようにレジストパターン103を除去した。
102 レジスト下層膜
103 レジストパターン
104 実施例1で調製されたコーティング組成物により形成された被覆膜
204 実施例5で調製されたコーティング組成物により形成された被覆膜
Claims (12)
- オルガノポリシロキサン、
下記式(1a)、式(1b)又は式(1c):
で表される有機溶媒を主成分とする溶剤、及び
第4級アンモニウム塩又は第4級ホスホニウム塩を含む、
レジストパターンを被覆する膜を形成するためのリソグラフィー用コーティング組成物。 - 請求項1において、前記オルガノポリシロキサンはかご型、ラダー型、直鎖型又は分岐型の主鎖を有するリソグラフィー用コーティング組成物。
- ポリシラン、
下記式(1a)、式(1b)又は式(1c):
で表される有機溶媒を主成分とする溶剤、及び
架橋剤、第4級アンモニウム塩、第4級ホスホニウム塩及びスルホン酸化合物からなる群から選択される少なくとも1種を含み、
前記ポリシランはその末端にシラノール基又は該シラノール基と水素原子を有し、
レジストパターンを被覆して塗布されるものである、リソグラフィー用コーティング組成物。 - 請求項4において、前記ポリシランは直鎖型又は分岐型の主鎖を有するリソグラフィー用コーティング組成物。
- 請求項4乃至請求項6のいずれか一項において、前記架橋剤は、メチロール基又はアルコキシメチル基が結合した窒素原子を2つ乃至4つ有する含窒素化合物である、リソグラフィー用コーティング組成物。
- 請求項1乃至請求項7のいずれか一項において、前記有機溶媒は4-メチル-2-ペンタノール、プロピレングリコールn-プロピルエーテル、プロピレングリコールn-ブチルエーテル、プロピレングリコールフェニルエーテル、ジプロピレングリコールn-プロピルエーテル、ジプロピレングリコールn-ブチルエーテル、ジプロピレングリコールジメチルエーテル、トリプロピレングリコールメチルエーテル、プロピレングリコールジアセテート、シクロヘキサノールアセテート又はシクロヘキサノールであるリソグラフィー用コーティング組成物。
- 請求項1乃至請求項8のいずれか一項において、前記コーティング組成物はさらに有機酸を含む、リソグラフィー用コーティング組成物。
- 請求項1乃至請求項9のいずれか一項において、前記コーティング組成物はさらに界面活性剤を含む、リソグラフィー用コーティング組成物。
- 被加工層が形成された半導体基板上に有機レジストを用いて第1のレジストパターンを形成する工程、前記第1のレジストパターンを被覆するように請求項1乃至請求項10のいずれか一項に記載のコーティング組成物を塗布する工程、前記コーティング組成物をベークして被覆膜を形成する工程、前記被覆膜をエッチングして前記第1のレジストパターンの上部を露出させる工程、及び前記第1のレジストパターンの一部又は全部を除去することにより前記被覆膜のパターンを形成する工程を含む、パターン形成方法。
- 請求項11において、前記被覆膜を形成する工程の後であって前記第1のレジストパターンの上部を露出させる工程の前に、有機レジストを用いて前記被覆膜上に第2のレジストパターンを形成する工程、及び前記第2のレジストパターンをマスクとして前記被覆膜をエッチングする工程をさらに含む、パターン形成方法。
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JP6999408B2 (ja) | 2016-12-28 | 2022-02-04 | 東京応化工業株式会社 | 樹脂組成物、樹脂組成物の製造方法、膜形成方法及び硬化物 |
US11718717B2 (en) | 2016-12-28 | 2023-08-08 | Tokyo Ohka Kogyo Co., Ltd. | Resin composition, method for producing resin composition, film formation method, and cured product |
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TWI481970B (zh) | 2015-04-21 |
TW201022862A (en) | 2010-06-16 |
KR101541439B1 (ko) | 2015-08-03 |
US20110117746A1 (en) | 2011-05-19 |
CN102084301A (zh) | 2011-06-01 |
KR20110034024A (ko) | 2011-04-04 |
JP5397636B2 (ja) | 2014-01-22 |
JPWO2010010928A1 (ja) | 2012-01-05 |
CN102084301B (zh) | 2013-08-28 |
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