WO2007036982A1 - イソシアヌル酸化合物と安息香酸化合物との反応生成物を含む反射防止膜形成組成物 - Google Patents
イソシアヌル酸化合物と安息香酸化合物との反応生成物を含む反射防止膜形成組成物 Download PDFInfo
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- WO2007036982A1 WO2007036982A1 PCT/JP2005/017735 JP2005017735W WO2007036982A1 WO 2007036982 A1 WO2007036982 A1 WO 2007036982A1 JP 2005017735 W JP2005017735 W JP 2005017735W WO 2007036982 A1 WO2007036982 A1 WO 2007036982A1
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
Definitions
- Antireflective film-forming composition comprising a reaction product of an isocyanuric acid compound and a benzoic acid compound
- the present invention relates to a composition for forming an antireflection film. Specifically, in a lithography process for manufacturing a semiconductor device, an antireflection film that reduces the reflection of exposure light on the photoresist layer applied on the semiconductor substrate from the semiconductor substrate, and a composition for forming the antireflection film About. More specifically, the present invention relates to an antireflection film used in a lithography process of semiconductor device manufacturing performed using exposure irradiation light having a wavelength of 248 nm, 193 nm, and 157 nm, and a composition for forming the antireflection film. Related. The present invention also relates to a method for forming a photoresist pattern using the antireflection film. Background art
- microfabrication by lithography using a photoresist composition has been performed in the manufacture of semiconductor devices.
- the microfabrication is obtained by forming a thin film of a photoresist composition on a silicon wafer, irradiating it with actinic rays such as ultraviolet rays through a mask pattern on which a semiconductor device pattern is drawn, and developing it.
- actinic rays such as ultraviolet rays
- This is a processing method in which a silicon wafer is etched using the resist pattern as a protective film.
- the antireflection film there are known an inorganic antireflection film such as titanium, titanium dioxide, titanium nitride, chromium oxide, carbon, a silicon, and an organic antireflection film composed of a light-absorbing substance and a polymer compound. It has been.
- the former requires equipment such as vacuum deposition equipment, CVD equipment, and sputtering equipment for film formation, while the latter is advantageous in that it does not require special equipment, and many studies have been conducted. For example, as described in US Pat.
- Acrylic-resin-type antireflection film having a hydroxyl group and a light-absorbing group in the same molecule as the cross-linking substituent described above, and a hydroxyl group and a light-absorbing group as described in US Pat. No. 5693691. Examples thereof include novolak-resin-type antireflection films in the same molecule.
- Physical properties desired as an organic antireflection film include a large absorbance to light and radiation, and no intermixing with a photoresist layer (insoluble in a photoresist solvent). Antireflective film material strength at the time of coating or heating and drying There is no low molecular diffusion in the top-coated photoresist, and there is a large dry etching rate compared to the photoresist.
- the antireflection film is required to be able to form a photoresist pattern having a good shape.
- it is required to be able to form a photoresist pattern that does not have a large footing. This is because if the photoresist pattern has a large skirt shape, it adversely affects the subsequent processing steps.
- an antireflection coating composition containing a rosin binder, a photoacid generator, and the like is known (see, for example, Patent Document 6).
- An antireflection film-forming composition containing a generated compound or the like is known (for example, see Patent Document 7).
- Patent Document 1 Japanese Patent Laid-Open No. 11-279523
- Patent Document 2 JP-A-10-204110
- Patent Document 3 Pamphlet of International Publication No. 02Z086624
- Patent Document 4 European Patent Application Publication No. 1298492 Specification
- Patent Document 5 European Patent Application Publication No. 1298493
- Patent Document 6 JP-A-11 133618
- Patent Document 7 Japanese Patent Laid-Open No. 11-38622
- the present invention relates to an antireflection film-forming composition for lithography for an antireflection film having strong absorption in light having a short wavelength, particularly light having a wavelength of 193 nm or 157 nm.
- an object of the present invention is to provide an antireflection film-forming composition that can be used in a lithography process for manufacturing a semiconductor device using irradiation light of an ArF excimer laser (wavelength 193 nm) or F2 excimer laser (wavelength 157 nm). Is to provide things.
- Another object of the present invention is to effectively absorb the reflected light from the substrate when the ArF excimer laser or F2 excimer laser irradiation light is used for microfabrication, and does not cause intermixing with the photoresist layer.
- Anti-reflection with higher dry etching rate than resist It is to provide a film and an antireflection film-forming composition therefor.
- a further object of the present invention is to provide an antireflective film that can form a photoresist pattern that does not have a large skirt shape at the bottom, and an antireflective film forming composition therefor.
- Another object of the present invention is to provide a method for forming an antireflection film for lithography and a method for forming a photoresist pattern using such an antireflection film forming composition.
- antireflection including a reaction product of an isocyanuric acid compound having two or three 2,3-epoxypropyl groups and a benzoic acid compound.
- the present inventors have found that an antireflection film having excellent performance can be formed from a film-forming composition in a process using light having a short wavelength, particularly ArF excimer laser and F2 excimer laser.
- R is an alkyl group having 1 to 6 carbon atoms, benzyl group, 2-probe group, 2, 3-
- An antireflective film-forming composition comprising either or both,
- the antireflection film-forming composition according to claim 1 comprising the reaction product, a crosslinkable compound, a solvent, and an acid compound,
- the antireflection film-forming composition according to claim 1, comprising, as a third aspect, the reaction product, a photoacid generator, a crosslinkable compound, and a solvent.
- reaction product photoacid generator, crosslinkable compound, solvent, and acid
- composition for forming an antireflection film according to claim 1, comprising a compound,
- the anti-reflection film forming composition according to any one of the first to fourth aspects, wherein the benzoic acid compound is a hydroxybenzoic acid compound having a halogen substituent,
- the antireflection film-forming composition according to the sixth aspect wherein the halogen substituent is a bromo group or an iodine group,
- the hydroxybenzoic acid compound having a halogen substituent is 2,5-dichlorodihydroxy-3hydroxy-1-methoxybenzoic acid, 2,4,6 torodo-3 hydroxybenzoic acid, 4, 6 Tribromo-3 Hydroxybenzoic acid, 2 Bromo-4, 6 Dimethylo-3 Hydroxybenzoic acid, 2 Fluoro-5-hydroxybenzoic acid, 3, 5 Jib Mouth 4 Hydroxybenzoic acid, 2, 4 Dihydroxy mono-5-bromobenzoic acid , 3-Toro 4-hydroxybenzoic acid, 4-chlorobenzoic acid 2-hydroxybenzoic acid, 3, 5-Jordo 2 hydroxybenzoic acid, 4-amino-3, 5-Jordo 2 hydroxybenzoic acid, and 3,5 Jib mouth Anti-reflection film-forming composition according to the sixth aspect, which is a compound selected from the group power of Mo 2 hydroxybenzoic acid, etc.,
- the reaction product of the compound represented by the formula (1) and the benzoic acid compound includes the compound represented by the formula (1) and the benzoic acid compound, Compound represented by formula (1): As a benzoic acid compound, it is a reaction product obtained by reacting at a molar ratio of 1: 2 to 1: 3. Antireflection film forming composition as described,
- an antireflection film obtained by applying the composition for forming an antireflection film according to any one of the first to ninth aspects on a semiconductor substrate and baking the composition An antireflection film forming composition according to any one of the viewpoints to the ninth aspect is applied to a semiconductor substrate and baked to form an antireflection film, and a photoresist layer is formed on the antireflection film.
- a method of forming a photoresist pattern used for manufacturing a semiconductor device comprising: exposing a coated semiconductor substrate; and developing the photoresist layer after the exposure; as a twelfth aspect, according to the first aspect to the ninth aspect
- An antireflection film forming composition according to any one of the above, a step of applying the composition on a semiconductor substrate and baking to form an antireflection film, a step of forming a photoresist layer on the antireflection film, the antireflection film And a semiconductor substrate coated with the photoresist layer with a F2 excimer laser (wavelength: 157 nm) exposure step, and a photoresist pattern used for manufacturing a semiconductor device, the step of developing the photoresist layer after the exposure step Forming method.
- the present invention is a composition for forming an antireflection film exhibiting strong absorption with respect to short-wavelength light, particularly ArF excimer laser (wavelength 193 nm) and F2 excimer laser (wavelength 157 nm ).
- the obtained antireflection film efficiently absorbs the reflected light having the substrate strength.
- the reflected light is effectively absorbed by the power of the semiconductor substrate, and does not cause intermixing with the photoresist layer.
- a preventive film can be provided.
- an antireflection film capable of forming a photoresist pattern having almost no skirt shape at the bottom.
- a favorable photoresist pattern can be formed in a lithography process using an ArF excimer laser (wavelength 193 ⁇ m) or the like.
- the present invention comprises an antireflection film-forming composition comprising a reaction product of a compound represented by the formula (1) and a benzoic acid compound, a photoacid generator, a crosslinkable compound, and a solvent. Concerning things.
- the present invention also includes a reaction product of the compound represented by the formula (1) and a benzoic acid compound, a photoacid generator, a crosslinkable compound, a solvent, and an acid compound.
- the present invention relates to an antireflection film-forming composition.
- the present invention also relates to an antireflection film-forming composition comprising a reaction product of a compound represented by the formula (1) and a benzoic acid compound, a crosslinkable compound, a solvent, and an acid compound.
- the antireflection film-forming composition of the present invention has other components. Limer components, light-absorbing compounds, surfactants and the like can be included.
- the ratio of the solid content is not particularly limited as long as each component is uniformly dissolved in the solvent, but is, for example, 0.5 to 50% by mass. Or 1 to 30% by mass, or 10 to 25% by mass.
- the solid content is a value obtained by removing all components and solvent components of the composition for forming an antireflection film.
- the antireflection film-forming composition of the present invention contains a reaction product of the compound represented by the formula (1) and a benzoic oxide compound.
- R is an alkyl group having 1 to 6 carbon atoms.
- alkyl group examples include a methyl group, an ethyl group, an isopropyl group, a cyclohexyl group, and a normal pentyl group.
- the reaction of the compound represented by the formula (1) with a benzoic acid compound includes benzene, toluene, xylene, ethyl lactate, butyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, In addition, it is preferably carried out in a solution state dissolved in an organic solvent such as N-methylpyrrolidone.
- an organic solvent such as N-methylpyrrolidone.
- quaternary ammonium salts such as benzyltriethyl ammonium chloride, tetraptyl ammonium chloride, and tetraethyl ammonium bromide can be used as a catalyst.
- the reaction temperature and reaction time of this reaction depend on the compound used, concentration, etc.
- Power reaction time 0.1 to: LOO time or 1 to 50 hours, reaction temperature 20 ° C to 200 ° C or 50
- the range force between ° C and 180 ° C is selected as appropriate.
- a catalyst it can be used in the range of 0.001 to 30% by mass relative to the total mass of the compound used.
- the ratio of the compound represented by the formula (1) and the benzoic acid compound used in the reaction is a molar ratio of the compound represented by the formula (1): the benzoic acid compound.
- the reaction product contained in the antireflection film-forming composition of the present invention can be obtained, for example, as follows.
- the compound represented by the formula (1) and the benzoic acid compound are dissolved in a suitable organic solvent so that the molar ratio is 1: 2 to 1: 3 and the concentration is 15 to 35% by mass.
- quaternary ammonium salts such as benzyltriethyl ammonium chloride are removed from the organic solvent. It is added at a ratio of 0.5 to 3% by mass relative to the total mass of the compound used.
- a reaction product can be obtained by reacting at a reaction temperature of 100 ° C. to 150 ° C. and a reaction time of 10 to 30 hours.
- the compound represented by the formula (1) and the benzoic acid compound are mixed in a suitable organic solvent so that the molar ratio is 1: 2 to 1: 3 and the concentration force is 0 to 60% by mass. Dissolve. Thereafter, a reaction product can be obtained by reacting at a reaction temperature of 100 ° C. to 150 ° C. and a reaction time of 10 to 30 hours without adding a quaternary ammonium salt.
- reaction of the compound of the formula (1) and the benzoic acid compound is dependent on the ratio of those compounds used in the reaction, but the reaction product may be the above formula.
- One of the 2,3-epoxypropyl groups in (1) is a compound converted to the group of the above formula (2), and two 2,3-epoxypropyl groups are in the above formula (2).
- R is 2,3-epoxypropyl group
- reaction product of the compound represented by the formula (1) and the benzoic acid compound may be a kind of compound or a mixture of two or more kinds of compounds.
- the reaction product of the compound represented by the formula (1) and the benzoic acid compound contained in the antireflection film-forming composition of the present invention is a kind of chemical compound. It may be a compound or a mixture of two or more compounds.
- the benzoic acid compound used for the reaction with the compound represented by the formula (1) is a hydroxybenzoic acid compound or a compound having two carboxyl groups, such as a phthalic acid compound.
- a hydroxybenzoic acid compound or a compound having two carboxyl groups such as a phthalic acid compound.
- both the carboxyl group and hydroxyl group of the compound or two carboxyl groups are considered to cause an epoxy ring-opening reaction with the 2,3-epoxypropyl group of the above formula (1). .
- reaction product having the structure of Formula (4) when reacting with the remaining carboxyl group or hydroxyl group power of Formula (3) and another 2,3-epoxypropyl group of Formula (1), a reaction product having the structure of Formula (4) below: It is possible to produce a thing. Furthermore, it is conceivable that the structure of the formula (4) is continuous, that is, an oligomer (or polymer) reaction product is produced.
- the reaction product is one kind of compound, or two or more kinds of compounds. (Or a polymer), or a mixture thereof.
- the reaction product contained in the composition for forming an antireflective film of the present invention may be!
- the compound represented by the formula (1) used for the reaction product contained in the composition for forming an antireflective film of the present invention includes 2-probeludiglycidyl isocyanuric acid, phenol. And diruglycidyl isocyanuric acid and tris (2,3 epoxypropyl) isocyanuric acid.
- the benzoic acid compound used for the reaction product contained in the antireflection film-forming composition of the present invention is not particularly limited.
- benzoic acid can be used.
- alkyl groups such as methyl, ethyl and isopropyl groups, alkoxy groups such as methoxy, ethoxy and butoxy groups, alkoxycarbonyl groups such as methoxycarbol and propoxycarbol groups, fluorine atoms, Halogen substituents such as bromine and iodine atoms, benzyl, furyl, phenoxy, hydroxyl, nitro, cyano, carboxyl, methylthio and amino groups Benzoic acid compounds can be used.
- benzoic acid compounds include benzoic acid, isophthalic acid monoethyl ester, 2,4 dibromobenzoic acid, 4-methylbenzoic acid, 2-methoxybenzoic acid, 2, 3, 5 triiodide.
- benzoic acid examples include a hydroxybenzoic acid compound, and a hydroxybenzoic acid compound having a halogen substituent is preferable.
- the halogen substituent is preferably a bromo group (one Br) or an odo group (one I) from the viewpoint of absorption with respect to F2 excimer laser.
- Hydroxybenzoic acid compounds include, for example, 4-hydroxybenzoic acid, 3-hydroxybenzoic acid, 3,5 dihydroxybenzoic acid, 2 amino-3 hydroxybenzoic acid, 2,5 dichloro-3-hydroxy-6 —Methoxybenzoic acid, 2, 4, 6 torodo 3 hydroxybenzoic acid, 2, 4, 6 Trib Mouth 3 hydroxybenzoic acid, 2 bromo-4,6 dimethyl-3 hydroxybenzoic acid, 2 fluoro-5 hydroxybenzoic acid, 3— Methoxy-4-hydroxydroxybenzoic acid, 3,5 dib-mouthed 4-hydroxybenzoic acid, 2,4 dihydroxy-5 bromobenzoic acid, 3 iodine 5-hydroxybenzoic acid, 2-hydroxybenzoic acid, 4-chloro-2-hydroxybenzoic acid Acid, 3, 5 Jordan 2 Hydroxybenzoic acid, 3-Methoxy-2-hydroxybenzoic acid, 2-Hydroxy-1-6-Isopropyl-3 — Mention may be made of methylbenzoic acid and 4-amin
- benzoic acid compounds In the reaction with the compound represented by the formula (1), only one kind of these benzoic acid compounds can be used. Also, two or more kinds of benzoic acid compounds can be used in appropriate combination. For example, 4-trobenzoic acid and 3,5 Jordan 2 hydroxybenzoic acid can be used in combination. Also, for example, 4-hydroxybenzoic acid and 4-cyanobenzoic acid can be used in combination. In addition, for example, 4-hydroxybenzoic acid and 2,3,5 triodobenzoic acid can be used in combination.
- the content of the reaction product of the compound represented by the formula (1) and the benzoic acid compound contained in the antireflection film-forming composition of the present invention is, for example, 50 to 99% by mass in the solid content. Or 60 to 95% by mass, or 65 to 90% by mass.
- the antireflection film-forming composition of the present invention can contain a photoacid generator. Since the photoacid generator generates an acid when the photoresist is exposed, the acidity of the antireflection film can be adjusted. This is a method for adjusting the acidity of the antireflection film to the acidity of the upper photoresist. In addition, by adjusting the acidity of the anti-reflective film, formed in the upper layer The pattern shape of the photoresist to be adjusted can be adjusted.
- the photoacid generator include form salt compounds, sulfonimide compounds, and disulfonyl diazomethane compounds.
- salt salts include diphenyl-hexahexafluorophosphate, disulfide-muodo-umtrifnoroleoromethane sulphonate, diphloe-denomnonaf, rononoremanolebutans.
- sulfonimide compound examples include N— (trifluoromethanesulfo-loxy) succinimide, N— (nonafluoronormalbutanesulfo-loxy) succinimide, N— (camphorsulfo-loxy) succinimide and N— (Trifluoromethanesulfoxy) naphthalimide and the like.
- Examples of the disulfo-diazomethane compound include bis (trifluoromethylsulfo) diazomethane, bis (cyclohexylsulfo) diazomethane, bis (phenylsulfo) diazomethane, and bis (p-toluenesulfo).
- photoacid generators include benzoin tosylate, pyrogallol methanesulfonic acid triester and -trobenzyl-9,10-jetoxyanthracene-2-sulfonate and phenol-bis (trichloromethyl) — S-triazine and the like.
- photoacid generators can be used alone or in combination of two or more.
- the content of the photoacid generator in the antireflection film-forming composition of the present invention includes a solid content. Among them, for example, 0.01 to 10% by mass, or 0.1 to 5% by mass, or 0.5 to 3% by mass.
- the antireflection film-forming composition of the present invention may contain a crosslinkable compound.
- a crosslinkable compound is not particularly limited, but a crosslinkable compound having at least two crosslinkable substituents is preferably used.
- examples thereof include nitrogen-containing compounds having two or more nitrogen atoms substituted with a hydroxymethyl group or an alkoxymethyl group. This is, for example, a nitrogen-containing compound having two or more nitrogen atoms substituted with a group such as a hydroxymethyl group, a methoxymethyl group, an ethoxymethyl group, a butoxymethyl group, and a hexyloxymethyl group.
- nitrogen-containing compounds examples include melamine compounds, benzoguanamine compounds and substituted urea compounds having a methylol group, a methoxymethyl group, and a crosslink forming substituent.
- compounds such as methoxymethyl isopropyl glycoluril, methoxymethyl benzobenzoamine and methoxymethylated melamine can be mentioned.
- the crosslinkable compound may be a hydroxymethyl group or alkoxymethyl group such as N-hydroxymethylacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylacrylamide, N-butoxymethylmethacrylamide.
- Polymers produced using substituted acrylamide compounds or methacrylamide compounds can be used. Examples of such a polymer include poly (N-butoxymethylacrylamide), a copolymer of N-butoxymethylacrylamide and styrene, a copolymer of N-hydroxymethylmethacrylamide and methylmetatalate, and N-ethoxy.
- crosslinkable compounds can cause a crosslinking reaction by self-condensation. Further, it can cause a crosslinking reaction with a hydroxyl group in the reaction product of the compound represented by the formula (1) and the benzoic acid compound. And the antireflection film formed by such a crosslinking reaction becomes strong. And it becomes an antireflection film having low solubility in an organic solvent.
- the crosslinkable compound only one kind may be used, or two or more kinds may be used in combination.
- the content of the crosslinkable compound in the antireflection film-forming composition of the present invention is, for example, 0.1 to 40% by mass, 0.1 to 35% by mass, or 5 in the solid content. ⁇ 30% by weight.
- the antireflection film-forming composition of the present invention may contain an acid compound.
- Acid compounds include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, sulfosalicylic acid, citrate, benzoic acid, and hydroxybenzoic acid. ⁇ composites.
- An aromatic sulfonic acid compound can also be used as the acid compound.
- aromatic sulfonic acid compounds include p-toluenesulfonic acid, pyridinium-p-toluenesulfonate, sulfosalicylic acid, 4-chlorobenzene sulfonic acid, 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1 naphthalene sulfonic acid, pyridinium 1 naphthalene sulfonic acid and the like. These acid compounds can be used alone or in combination of two or more.
- the content of the acid compound in the antireflective film-forming composition of the present invention is, for example, 0.01 to 10% by mass, 0.1 to 5% by mass, or 0. 5-3% by mass.
- the antireflection film-forming composition of the present invention may further contain a polymer component, a light-absorbing compound, a surface active agent, and the like.
- the polymer component is not particularly limited, but a polymer having at least one cross-linking substituent selected from a hydroxyl group, a carboxyl group, an amino group, and a thiol group is preferable.
- a polymer having at least one cross-linking substituent selected from a hydroxyl group, a carboxyl group, an amino group, and a thiol group is preferable.
- Such polymers include 2-hydroxyethyl talylate, 2-hydride Listed are polymers containing one of the structural units such as loxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, butyl alcohol, 2-hydroxyethyl butyl ether, acrylic acid, and methacrylic acid. be able to.
- the weight average molecular weight (in terms of standard polystyrene) of such a polymer is preferably 500 to 1,000,000, ⁇ 500 to 500,000, and 1000 to 100,000.
- the content thereof is 0.1 to 20% by mass or 0.1 to 10% by mass in the solid content.
- Such polymers include, for example, poly 2 hydroxyethinoremethacrylate, polyvinyl alcohol, polyacrylic acid, a copolymer of 2-hydroxypropyl acrylate and methyl methacrylate, 2-hydroxypropyl acrylate and anthryl.
- Examples of the polymer include phenol novolak, cresol novolak, and naphthol novolak.
- the light-absorbing compound is not particularly limited as long as it has high absorptivity for light in the photosensitive characteristic wavelength region of the photosensitive component in the photoresist layer provided on the antireflection film. can do.
- Examples of the light-absorbing compound include a benzophenone compound, a benzotriazole compound, an azo compound, a naphthalene compound, an anthracene compound, an anthraquinone compound, a triazine compound, a triazine trione compound, and a quinoline compound. Such Can be used.
- naphthalene carboxylic acid 2-naphthalene carboxylic acid, 1-naphthol, 2-naphthol, naphthyl acetic acid, 1-hydroxy 1-2 naphthalene carboxylic acid, 3 hydroxy 1-2 naphthalene carboxylic acid, 3, 7 Dihydroxy 2 Naphthalenecarboxylic acid, 6 Bromo-2 hydroxynaphthalene, 2, 6 Naphthalene dicarboxylic acid, 9 Anthracene carboxylic acid, 10 Bromo 9 Anthracene carboxylic acid, Anthracene 9, 10 Dicarboxylic acid, 1 Anthracene carboxylic acid, 1-Hydroxy Anthracene, 1, 2, 3 Anthracentriol, 9 Hydroxymethylanthracene, 2, 7, 9 Anthracentriol, Benzoic acid, 4-Hydroxybenzoic acid, 4 Bromobenzoic acid, 3 Yoodobenzoic acid, 2, 4, 6 Trihydroxy 2 Naphthal
- surfactant examples include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene vinyl ether, polyoxyethylene octyl phenol ether, polyoxy Polyoxyethylene alkylaryl ethers such as ethylene nonylphenol ether, polyoxyethylene polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, resonatebitan monostearate, sorbitan monooleate, sorbitan trioleate Sorbitan fatty acid esters such as sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as lensorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, Product name F-top EF301,
- surfactants may be used alone or in combination of two or more.
- the content thereof is from 0.0001 to 5 mass% or from 0.001 to 2 mass% in the solid content.
- the surfactant is effective in suppressing the occurrence of pinholes, strains and the like during application of the antireflection film-forming composition.
- a rheology modifier, an adhesion aid, and the like can be added to the antireflection film-forming composition of the present invention as necessary.
- the rheology modifier improves the fluidity of the antireflection film-forming composition, and is effective in increasing the filling property of the antireflection film-forming composition into the hole, particularly in the firing step.
- Adhesion aids improve the adhesion between the semiconductor substrate or photoresist and the antireflection film, and are particularly effective in suppressing the peeling of the photoresist during development.
- rheology modifier examples include dimethyl phthalate, jetyl phthalate, diisobutyl phthalate, dihexyl phthalate, butyl isodecyl phthalate, dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decenorea diphosphate , Dinoremanolebutinoremalate, jetinoremalate, dinoninoremalate, methylolate, butyrate, tetrahydrofurfurolate, normal butyl stearate, glyceryl stearate and the like.
- adhesion assistant examples include trimethylchlorosilane, dimethylvinylchlorosilane, dimethinoregetoxysilane, methinoresinmethoxysilane, dimethylenovininoleethoxysilane, diphenyldimethoxysilane, phenyltriethoxy.
- Silane hexamethyldisilazane, N, N, -bis (trimethylsilyl) urea, dimethyltrimethylsilylamine, trimethylsilylimidazole, butyltrichlorosilane, ⁇ - clopropylpropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ - Silanes such as glycidoxypropyltrimethoxysilane, benzotriazole, benzimidazole, indazole, imidazole, 2-mercaptobenzimidazole, 2-mercaptobenzothiothiazole, 2-mercaptobe Zookisazo And urazole, thiouracil, mercaptoimidazole, mercaptopyrimidine, 1,1-dimethylurea, 1,3 dimethylurea, and thiourea compounds.
- the solvent used in the antireflection film-forming composition of the present invention can be used without particular limitation as long as it is a solvent that can dissolve the solid content.
- solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cetyl sorb acetate, cetyl solv acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monoole, propylene.
- Glycolemonomonomethylenoateolate Propyleneglycololemonomethinoate ether acetate, Propylene glycol propyl ether acetate, Toluene, Xylene, Methyl ethyl ketone, Cyclopentanone, Cyclohexanone, 2-Hydroxypropionate, 2 —Hydroxy 2-methylpropionate, ethoxy acetate, hydroxyethyl acetate, 2-hydroxy-3 methylbutanoate, 3-methoxypropyl Examples include methyl pionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethylpropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butylacetate, ethyl lactate, and butyl lactate. be able to.
- These solvents are used alone or in combination of
- a semiconductor substrate for example, a silicon Z-dioxide-silicon-coated substrate, a silicon nitride substrate, a silicon wafer substrate, a glass substrate, an ITO substrate, etc.
- an appropriate coating method such as a spinner or a coater.
- the antireflection film-forming composition of the present invention is applied, and then fired to form an antireflection film.
- the conditions for firing are appropriately selected from firing temperatures of 80 ° C. to 250 ° C. and firing times of 0.3 to 60 minutes.
- the firing temperature is 130 ° C to 250 ° C
- the firing time is 0.5 to 5 minutes.
- the thickness of the antireflection film to be formed is 0.01 to 3.
- a layer of photoresist is formed on the antireflection film. Formation of the photoresist layer can be performed by a well-known method, that is, by applying and baking a photoresist composition solution on the antireflection film.
- the photoresist applied and formed on the antireflection film of the present invention is not particularly limited as long as it is sensitive to exposure light.
- Either negative photoresist or positive photoresist can be used.
- a positive photoresist composed of novolac resin and 1,2-naphthoquinonediazide sulfonate, a binder having a group that decomposes with an acid to increase the alkali dissolution rate, and a chemically amplified photo with the ability to generate a photoacid generator Resist, chemically decomposed photoresist composed of low molecular weight compound that decomposes with acid to increase alkali dissolution rate of photoresist, Al force re-soluble binder and photoacid generator, and acid decomposes to increase alkali dissolution rate And a chemically amplified photoresist comprising a low-molecular compound and a photoacid generator that decomposes with a binder having an acid group and an
- a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), an F2 excimer laser (wavelength 157 nm), or the like can be used.
- post-exposure bake can be performed as necessary.
- the post-exposure heating is appropriately selected from a heating temperature of 70 ° C to 150 ° C and a heating time of 0.3 to 10 minutes.
- development is performed with a developer.
- a developer for example, when a positive photoresist is used, the exposed portion of the photoresist is removed, and a photoresist pattern is formed.
- Developers include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, hydroxide tetramethyl ammonium, and hydroxide tetraethyl ammonium.
- alkaline aqueous solutions such as aqueous solutions of quaternary ammonium hydroxides such as -um and choline, and aqueous amine solutions such as ethanolamine, propylamine and ethylenediamine.
- aqueous amine solutions such as ethanolamine, propylamine and ethylenediamine.
- a surfactant or the like can be added to these developers.
- a temperature of 5 to 50 ° C and a time of 10 to 300 seconds are also selected as appropriate.
- the anti-reflection film is removed and the semiconductor substrate is processed using the photoresist pattern thus formed as a protective film. Removal of the anti-reflective coating can be accomplished using tetrafluoromethane, perfluorocyclobutane (C F), perfluoropropane (C F), trifluoro
- gases such as fluoromethane, carbon monoxide, argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, nitrogen trifluoride and chlorine trifluoride.
- a planarization film or a gap fill material layer may be formed before the antireflection film of the present invention is formed.
- a planarizing film or a gap fill material layer be formed before the antireflection film of the present invention is formed.
- the semiconductor substrate to which the composition for forming an antireflective film of the present invention is applied may have an inorganic antireflective film formed on its surface by a CVD method or the like.
- the antireflection film of the present invention can also be formed.
- the antireflection film of the present invention has an adverse effect on the substrate of a layer for preventing the interaction between the substrate and the photoresist, a material used for the photoresist, or a substance generated upon exposure to the photoresist.
- a layer that has a function to prevent diffusion a layer that has a function to prevent diffusion of a substance generated from the substrate during heating and baking into the upper photoresist, and a NORIA for reducing the voiding effect of the photoresist layer by the semiconductor substrate dielectric layer It is pretty easy to use as a layer.
- the antireflection film formed from the antireflection film forming composition is applied to a substrate on which a via hole used in a dual damascene process is formed, and is used as a filling material capable of filling the via hole without a gap. Can be used. Further, it can also be used as a flattening material for flattening the surface of a semiconductor substrate with unevenness.
- Tris (2,3-epoxypropyl) isocyanuric acid (trade name TE PIC, manufactured by Nissan Chemical Industries, Ltd.) 175g, 3,5-Jodo 2-hydroxybenzoic acid 628g, and benzyltriethyl ammonium chloride 9.2g was dissolved in 3250 g of propylene glycol monomethyl ether and then reacted at 130 ° C. for 24 hours to obtain a solution containing the reaction product.
- the reaction product is considered to include an isocyanuric oxide in which a 2,3-epoxypropyl group is converted to a group of formula (5) and an oligomer (or polymer) having the structure of formula (6).
- Tris (2,3-epoxypropyl) isocyanuric acid (trade name TE PIC, manufactured by Nissan Chemical Industries, Ltd.) 457g, 4-hydroxybenzoic acid 407g, 4-cianobenzoic acid 136g After dissolving in recall monomethyl ether lOOOOg, reaction was performed at 130 ° C for 24 hours to obtain a solution containing the reaction product.
- the reaction product is considered to include an isocyanuric acid compound in which a 2,3-epoxypropyl group is converted to a group of formula (7) or formula (8).
- the solution was filtered using a polyethylene microfilter having a pore size of 0.10 m, and then filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a solution of an antireflection film-forming composition.
- An antireflection film was prepared in the same manner as in Example 1 except that the following compounds were used in place of the triphenylsulfo-hexafluoroantimonate used in Example 1 as a photoacid generator. A solution of the forming composition was prepared.
- Trifluorosulfo-trifluoromethanesulfonate (Example 2), Trifluorosulfonium nonafluoronormalbutanesulfonate (Example 3), N- (trifluoromethane sulfo-loxy) succinimide (Example 4), diphenyl-trifluoromethanesulfonate (Example 5), bis (phenylsulfo) diazomethane (Example 6), phenol Rubis (trichloromethyl) s triazine (Example 7), N- (trifluoromethanesulfo-loxy) naphthalimide (Example 8), and bis (4-tert butylphenol) iodine trifluoromethanesulfonate (implemented) Example 9).
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 m, and then filtered using a polyethylene microfilter having a pore size of 0.05 m to prepare a solution for forming an antireflection film. did.
- the solution was filtered using a polyethylene microfilter having a pore diameter of 0.10 m, and then filtered using a polyethylene microfilter having a pore diameter of 0.05 m to prepare a solution of the antireflection film-forming composition.
- Each of the antireflection film-forming composition solutions prepared in Examples 1 to 11 was applied onto a semiconductor substrate (silicon wafer) using a spinner. It was baked on a hot plate at 205 ° C for 1 minute to form an antireflection film (film thickness 0.08 m). These antireflection films were immersed in ethyl acetate and propylene glycol monomethyl ether, which are solvents used for the photoresist, and confirmed to be insoluble in these solvents.
- Each of the antireflective film-forming composition solutions prepared in Examples 1 to 11 was applied onto a silicon wafer with a spinner. Baked on a hot plate at 205 ° C for 1 minute to prevent reflection A stop film (thickness 0.08 m) was formed. A commercially available photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR710) is applied onto these antireflection films with a spinner and heated at 90 ° C for 1 minute on the hot plate. Layers were formed. 90 after exposure of photoresist and post exposure bake. C for 1.5 minutes. After developing the photoresist, the thickness of the antireflection film was measured, and it was confirmed that intermixing between the antireflection film and the photoresist layer occurred.
- PAR710 commercially available photoresist solution
- Each of the antireflective film-forming composition solutions prepared in Examples 1 to 11 was applied onto a silicon wafer with a spinner. It was baked on a hot plate at 205 ° C for 1 minute to form an antireflection film (film thickness 0.06 m). Then, using these spectroscopic ellipsometers (manufactured by J.A. Woollam, VUV-VASE VU-302), the refractive index (n value) and attenuation coefficient (k value) at wavelengths of 193 nm and 157 nm were measured.
- the antireflection films from Examples 1 to 10 had a refractive index (n value) of 1.81 at a wavelength of 193 nm and an attenuation coefficient (k value) of 0.44.
- the antireflection films from Examples 1 to 10 had a refractive index (n value) of 1.60 at a wavelength of 157 nm and an attenuation coefficient (k value) of 0.44.
- the antireflection film of Example 11 has a refractive index (n value) of 1.69 at a wavelength of 193 nm and an attenuation coefficient (k value) of 0.47.
- Each of the antireflective film-forming composition solutions prepared in Examples 1 to 11 was applied onto a silicon wafer with a spinner. It was baked on a hot plate at 205 ° C for 1 minute to form an antireflection film (film thickness 0.08 m).
- a commercially available photoresist solution (trade name TARF-P6111 manufactured by Tokyo Ohka Kogyo Co., Ltd.) is applied to the upper layer of these antireflection films with a spinner and heated on a hot plate at 90 ° C for 1 minute.
- a photoresist layer (thickness 0.33 ⁇ m) was formed.
- the cross section of the resulting photoresist pattern was observed with a scanning electron microscope (SEM).
- SEM scanning electron microscope
- a slight skirt shape was observed below the photoresist.
- the skirting shape was inferior at the bottom of the photoresist.
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- Physics & Mathematics (AREA)
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- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05788391A EP1939688A4 (en) | 2005-09-27 | 2005-09-27 | COMPOSITION FOR THE FORMATION OF ANTIREFLECTIVE FILM, COMPRISING A PRODUCT OF THE REACTION BETWEEN AN ISOCYANURIC ACID COMPOUND AND A BENZOIC ACID COMPOUND |
US11/992,595 US11372330B2 (en) | 2005-09-27 | 2005-09-27 | Anti-reflective coating forming composition containing reaction product of isocyanuric acid compound with benzoic acid compound |
CNA2005800516391A CN101268419A (zh) | 2005-09-27 | 2005-09-27 | 含有异氰脲酸化合物与苯甲酸化合物的反应生成物的形成防反射膜的组合物 |
KR1020087009352A KR101226050B1 (ko) | 2005-09-27 | 2005-09-27 | 이소시아눌산 화합물과 안식향산 화합물의 반응 생성물을 포함하는 반사방지막 형성 조성물 |
PCT/JP2005/017735 WO2007036982A1 (ja) | 2005-09-27 | 2005-09-27 | イソシアヌル酸化合物と安息香酸化合物との反応生成物を含む反射防止膜形成組成物 |
Applications Claiming Priority (1)
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PCT/JP2005/017735 WO2007036982A1 (ja) | 2005-09-27 | 2005-09-27 | イソシアヌル酸化合物と安息香酸化合物との反応生成物を含む反射防止膜形成組成物 |
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WO2007036982A1 true WO2007036982A1 (ja) | 2007-04-05 |
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PCT/JP2005/017735 WO2007036982A1 (ja) | 2005-09-27 | 2005-09-27 | イソシアヌル酸化合物と安息香酸化合物との反応生成物を含む反射防止膜形成組成物 |
Country Status (5)
Country | Link |
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US (1) | US11372330B2 (ja) |
EP (1) | EP1939688A4 (ja) |
KR (1) | KR101226050B1 (ja) |
CN (1) | CN101268419A (ja) |
WO (1) | WO2007036982A1 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2011527461A (ja) * | 2008-07-08 | 2011-10-27 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
JP5168517B2 (ja) * | 2007-10-31 | 2013-03-21 | 日産化学工業株式会社 | レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
JP2014513312A (ja) * | 2011-02-08 | 2014-05-29 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 下層コーティング組成物および微細電子デバイスを製造するための方法 |
US10437150B2 (en) * | 2008-11-27 | 2019-10-08 | Nissan Chemical Industries, Ltd. | Composition for forming resist underlayer film with reduced outgassing |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US8221965B2 (en) | 2008-07-08 | 2012-07-17 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
US20100092894A1 (en) * | 2008-10-14 | 2010-04-15 | Weihong Liu | Bottom Antireflective Coating Compositions |
US8507192B2 (en) * | 2010-02-18 | 2013-08-13 | Az Electronic Materials Usa Corp. | Antireflective compositions and methods of using same |
JP6196194B2 (ja) * | 2014-08-19 | 2017-09-13 | 信越化学工業株式会社 | 紫外線吸収剤、レジスト下層膜形成用組成物、及びパターン形成方法 |
US11977333B2 (en) | 2019-07-31 | 2024-05-07 | Taiwan Semiconductor Manufacturing Company, Ltd. | Semiconductor devices and methods of manufacturing |
US20230042522A1 (en) * | 2021-07-23 | 2023-02-09 | Hewlett-Packard Development Company, L.P. | Inkjet composition |
CN116082914B (zh) * | 2022-11-24 | 2024-04-30 | 厦门恒坤新材料科技股份有限公司 | 一种有机抗反射涂层组合物及其制备方法和图案形成方法 |
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WO2002086624A1 (fr) * | 2001-04-10 | 2002-10-31 | Nissan Chemical Industries, Ltd. | Composition servant a former un film antireflet pour procede lithographique |
WO2004034148A1 (ja) | 2002-10-09 | 2004-04-22 | Nissan Chemical Industries, Ltd. | リソグラフィー用反射防止膜形成組成物 |
WO2004034435A2 (en) | 2002-10-08 | 2004-04-22 | Brewer Science, Inc. | Bottom anti-reflective coatings derived from small core molecules with multiple epoxy moieties |
JP2005062591A (ja) | 2003-08-18 | 2005-03-10 | Nissan Chem Ind Ltd | フォトレジストパターンの形成方法 |
WO2005098542A1 (ja) * | 2004-04-09 | 2005-10-20 | Nissan Chemical Industries, Ltd. | 縮合系ポリマーを有する半導体用反射防止膜 |
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2005
- 2005-09-27 KR KR1020087009352A patent/KR101226050B1/ko active IP Right Grant
- 2005-09-27 WO PCT/JP2005/017735 patent/WO2007036982A1/ja active Application Filing
- 2005-09-27 EP EP05788391A patent/EP1939688A4/en not_active Withdrawn
- 2005-09-27 US US11/992,595 patent/US11372330B2/en active Active
- 2005-09-27 CN CNA2005800516391A patent/CN101268419A/zh active Pending
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EP1560070A1 (en) | 2002-10-09 | 2005-08-03 | Nissan Chemical Industries, Ltd. | Composition for forming antireflection film for lithography |
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JP5168517B2 (ja) * | 2007-10-31 | 2013-03-21 | 日産化学工業株式会社 | レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
JP2011527461A (ja) * | 2008-07-08 | 2011-10-27 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
US10437150B2 (en) * | 2008-11-27 | 2019-10-08 | Nissan Chemical Industries, Ltd. | Composition for forming resist underlayer film with reduced outgassing |
JP2014513312A (ja) * | 2011-02-08 | 2014-05-29 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 下層コーティング組成物および微細電子デバイスを製造するための方法 |
Also Published As
Publication number | Publication date |
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US11372330B2 (en) | 2022-06-28 |
KR101226050B1 (ko) | 2013-01-24 |
US20090117493A1 (en) | 2009-05-07 |
EP1939688A1 (en) | 2008-07-02 |
CN101268419A (zh) | 2008-09-17 |
KR20080052670A (ko) | 2008-06-11 |
EP1939688A4 (en) | 2010-06-02 |
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