WO2007148627A1 - 水酸基含有縮合系樹脂を含有するレジスト下層膜形成組成物 - Google Patents
水酸基含有縮合系樹脂を含有するレジスト下層膜形成組成物 Download PDFInfo
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- WO2007148627A1 WO2007148627A1 PCT/JP2007/062142 JP2007062142W WO2007148627A1 WO 2007148627 A1 WO2007148627 A1 WO 2007148627A1 JP 2007062142 W JP2007062142 W JP 2007062142W WO 2007148627 A1 WO2007148627 A1 WO 2007148627A1
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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
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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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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
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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
- G03F7/094—Multilayer resist systems, e.g. planarising layers
Definitions
- the present invention relates to a novel resist underlayer film forming composition for lithography, an underlayer film formed from the composition, and a method for forming a photoresist pattern using the underlayer film.
- the present invention also provides a lower antireflection film for reducing the reflection of exposure light from a substrate applied on a semiconductor substrate in a lithography process for manufacturing a semiconductor device, and a hole formed in the semiconductor substrate.
- Lithographic resist underlayer film that can be used as a flattening film for flattening uneven semiconductor substrates, and a film that prevents contamination of photoresist by substances generated from the semiconductor substrate during heating and baking.
- a resist underlayer film forming composition for forming the underlayer film. Background
- 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.
- an antireflection film-forming composition containing a polymer having a pyrimidinetrione structure, an imidazolidinedione structure, an imidazolidinetrione structure, or a triazinetrione structure has been proposed (see Patent Document 1).
- Patent Document 1 International Publication No. 05Z098542 Pamphlet
- Patent Document 2 JP-A-8-325481
- An object of the present invention is to provide a resist underlayer film forming composition that can be used in the manufacture of a semiconductor device. Then, a resist underlayer film for lithography and a resist underlayer for forming the underlayer film that do not cause intermixing with the photoresist applied and formed on the upper layer and have a higher dry etching rate than the photoresist. It is to provide a film-forming composition.
- Another object of the present invention is to provide a resist underlayer film forming composition for lithography for forming a resist underlayer film having excellent hole filling properties on a semiconductor substrate.
- Another object of the present invention is to provide a lower layer that reduces reflection of exposure light on a photoresist formed on a semiconductor substrate, particularly ArF excimer laser (wavelength: 193 nm) from the substrate in a lithography process for manufacturing a semiconductor device.
- Lithographic resist lower layer that can be used as an anti-reflective film, a flat film for flattening an uneven semiconductor substrate, a film that prevents contamination of the photoresist by substances generated from the semiconductor substrate during heating and baking, etc.
- a resist underlayer film forming composition for forming a film and the underlayer film is provided.
- Another object of the present invention is to provide a method for forming a resist underlayer film for lithography using the composition for forming a lower layer film and a method for forming a photoresist pattern.
- Y represents an alkylene group having 1 to C carbon atoms, or an aromatic ring having 6 to 14 carbon atoms, and the alkylene group and the aromatic ring each have one or more hydroxyl groups, and the alkylene group and Aroma It has less than the number that can be substituted with a hydrogen atom of the group ring.
- a resist underlayer film forming composition for lithography comprising a polymer having a structure of
- the polymer has the formula (2):
- n represents the number of repeating units of 1 to 10, and R and R are a hydroxyl group
- Elemental atom, alkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, nitro group, cyano group, and halogen group power is the selected functional group, and the total number of hydroxyl groups of R and R
- a resist underlayer film forming composition for lithography according to the first aspect which is a polymer having a structure of
- the polymer is represented by the formula (3):
- n is an integer from 0 to 2
- b is an integer from l to (2n + 4)
- R is a ring substituent
- a resist underlayer film forming composition for lithography according to the first aspect which is a polymer having a structure of
- the polymer has the formula (4): X
- n represents the number of repeating units of 1 to L0, and R and R are each a hydroxyl group.
- the cardinal number is 1 or more and 2n or less.
- m represents the number of repeating units of 3 to: L000,
- Q is the formula (5), formula (6), formula (7), formula (8), formula (9), or formula (10):
- R is a ring substituent, each having an alkyl group having 1 to 6 carbon atoms,
- An alkoxy group having 6 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a halogen group, a nitro group, a cyano group, a hydroxyl group, or an alkylthio group having 1 to 6 carbon atoms, T is an integer of 1 to 4; 1 ⁇
- T is an integer from 1 to 6
- T is an integer from 1 to 8
- k is an integer from 1 to 10.
- R to R are each a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 3 carbon atoms.
- Group force may be substituted with a selected group.
- R and R, and R and R are bonded to each other to form a carbon atom.
- R is a hydrogen source
- the phenyl group includes an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, a hydroxyl group, and an alkylthio group having 1 to 6 carbon atoms. Force may be substituted with a selected group. ).
- the composition for forming a resist underlayer film for lithography according to the first aspect which is a polymer having the structure:
- n is an integer of 0 to 2
- b is an integer of 1 to (2n + 4)
- m is 3 to: the number of LOOO repeating units
- R is a ring substituent. Yes, each with hydroxyl groups and 1 to 6 carbon atoms
- a composition for forming a resist underlayer film for lithography described in the first aspect which is a polymer having a structure of
- the polymer is represented by the following formula (15):
- a resist underlayer film forming composition for lithography (Wherein m represents the number of repeating units of 3 to L000;), a resist underlayer film forming composition for lithography according to a first aspect,
- the polymer has the following formula (16):
- the resist underlayer film forming composition for lithography which is a polymer having a structure of:
- the resist underlayer film forming composition for lithography according to any one of the first to sixth aspects, further comprising a crosslinking agent,
- the resist underlayer film forming composition for lithography according to any one of the first aspect to the sixth aspect further including an acid compound and Z or an acid generator
- the tenth aspect A step of applying a resist underlayer film forming composition for lithography according to any one of the first aspect to the sixth aspect onto a semiconductor substrate and baking to form a resist underlayer film, a photoresist layer on the resist underlayer film
- a photoresist pattern used for manufacturing a semiconductor device comprising: a step of exposing a semiconductor substrate coated with the resist underlayer film and the photoresist layer; and a step of developing the photoresist layer after the exposure. This is a method for forming a film.
- the present invention is a composition for forming a resist underlayer film having absorption in short wavelength light, particularly ArF excimer laser (wavelength 193nm).
- the obtained resist underlayer film efficiently absorbs the reflected light from the substrate.
- the reflected light of a semiconductor substrate force is effectively absorbed, and no intermixing with the photoresist layer occurs.
- a resist underlayer film that can be easily removed by dry etching compared to a resist layer can be provided.
- a resist underlayer film suitable for combined use with a hard mask can be provided.
- a photoresist pattern having a good shape can be formed in one lithography process using light having a short wavelength.
- the resist underlayer film forming composition for lithography of the present invention comprises a polymer having a repeating unit structure represented by formula (1) and a solvent.
- the resist underlayer film forming composition for lithography of the present invention can further contain a crosslinkable compound, an acid compound, and an acid generator as optional components in the polymer and the solvent. Further, other components such as surfactants and rheology modifiers can be included.
- the polymer having the structure of formula (1) is an essential component.
- the proportion of the polymer having the structure of the formula (1) in the solid content of the resist underlayer film forming composition of the present invention is 50% by mass or more, preferably 60% by mass or more from the viewpoint of the antireflection effect.
- the ratio of the solid content in the resist underlayer film forming composition of the present invention is not particularly limited as long as each component is uniformly dissolved in the solvent.
- the force is 1 to 50% by mass, or 5 to 5%. 30% by mass or 10-25% by mass.
- the solid content is obtained by removing the solvent component from all the components of the resist underlayer film forming composition for lithography.
- Y represents an alkylene group having 1 to 10 carbon atoms or an aromatic ring having 6 to 14 carbon atoms.
- aromatic ring having 6 to 14 carbon atoms examples include benzene ring, naphthalene ring and anthracene ring.
- the number of hydroxyl groups is one or more, and can exist up to the maximum number that can be substituted with hydrogen atoms of the alkylene group and aromatic ring.
- polymer having the structure of the above formula (1) include a polymer having the structure of the formula (2).
- n represents the number of repeating units of 1 to 10
- R and R are each a hydroxy acid
- Group a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, a naphthyl group, a nitro group, a cyano group, and a halogen group.
- the total number of hydroxyl groups 1 and 2 is 1 or more and 2n or less.
- Specific examples of the alkyl group in R and R include
- Examples thereof include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, and a normal hexyl group.
- a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are used.
- 1 to 2 hydroxyl groups can exist
- 1 to 12 hydroxyl groups can exist.
- the portion of the repeating unit containing R and R as a group is an alkylene group
- Straight chain alkylene groups such as a methylene group, an ethylene group, a normal propylene group, a normal hexylene group, a normal pentylene group and a normal octylene group;
- An alkylene group having 1 to 4 carbon atoms is preferred, and an ethylene group having 2 carbon atoms is particularly preferred.
- the partial structure of the formula (2) containing these alkylene groups is derived from a linear aliphatic dicarboxylic acid, and the linear aliphatic dicarboxylic acid is, for example, [1 1] to [1-11]:
- a polymer having the structure of the formula (2) is obtained using the linear aliphatic dicarboxylic acid exemplified in [1-1 0] [] as a raw material.
- the number of repeating units n is 1 to 10.
- the force R and the total number of hydroxyl groups contained in R are Z
- the resist underlayer film comprising the polymer having the structure of formula (2) is close to the force saturation in which at least one of the resist underlayer films is indispensable for improving the etching rate in the lithography process.
- the number is present, the polarity of the obtained polymer becomes high and the solubility in the solvent decreases. Therefore, l ⁇ Z ⁇ n, n is preferably 1 ⁇ 4.
- a polymer having a structure of the formula (2) using a dicarboxylic acid derived from tartaric acid is preferable.
- a polymer having the structure of the formula (3) can be given.
- n 0 2
- R is the water present in the ring
- Substituents substituted by elemental atoms which include hydroxyl groups, hydrogen atoms, alkyl groups having 16 carbon atoms, phenol groups, naphthyl groups, nitro groups, cyan groups, and halogen groups.
- the total number of hydroxyl groups in R is 1 or more and (2n + 4) or less
- alkyl group in R include a methyl group, an ethyl group, and isopropyl.
- the partial structure of formula (3) is derived from an aromatic dicarboxylic acid, and examples of the aromatic dicarboxylic acid include [2-1] [2-6]:
- the number of repeating units n is 0 2. Since the number of substituents of R is l to (2n + 4), R The number of hydroxyl groups based on is from 1 to (2n + 4).
- a polymer having a structure of the formula (3) using a dicarboxylic acid derived from hydroxyphthalic acid is preferable.
- polymer of the formula (1) examples include a polymer of the formula (4).
- n represents the number of repeating units of 1 to 10
- R and R are a hydroxyl group and water, respectively.
- the group examples include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, and a normal hexyl group.
- a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is used.
- Q is a divalent organic group, and examples thereof include Formula (5), Formula (6), Formula (7), Formula (8), Formula (9), and Formula (10).
- R is a ring substituent, each having 1 to 6 carbon atoms.
- an alkoxy group having 1 to 6 carbon atoms an alkenyl group having 3 to 6 carbon atoms, a halogen group, a nitro group, a cyano group, a hydroxyl group, or an alkylthio group having 1 to 6 carbon atoms.
- alkyl group examples include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, and a cyclohexyl group.
- alkoxy group examples include a methoxy group, an ethoxy group, a normal pentyloxy group, an isopropoxy group, and a cyclohexyloxy group.
- alkylthio group examples include a methylthio group, an ethylthio group, a normal pentylthio group, an isopropylthio group, and a cyclohexylthio group.
- the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- T, T, T and T are the number of substituents substituted on the ring, and T is Is an integer from 1 to 4, T is an integer from 1 to 10, ⁇ is an integer from 1 to 6, and ⁇ is from 1 to 8
- alkylene groups are alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, halogen groups, nitro groups, cyano groups, hydroxyl groups, or carbon atoms 1 It may be substituted with ⁇ 6 alkylthio groups.
- XI includes the formula (11), the formula (12), or the formula (13).
- R to R are each a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 3 to 6 carbon atoms.
- the group force may be substituted with a selected group.
- R and R, and R and R are bonded to each other to form a carbon atom.
- R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, carbon
- the phenol group is an alkyl group having 1 to 6 carbon atoms, a halogen atom, or a carbon atom having 1 to
- a group force consisting of 6 alkoxy groups, nitro groups, cyan groups, hydroxyl groups, and alkylthio groups having 1 to 6 carbon atoms may also be substituted with a selected group.
- Specific examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, a normal butyl group, and a cyclohexyl group.
- alkoxy group examples include a methoxy group, an ethoxy group, a normal pentyloxy group, an isopropoxy group, and a cyclohexyloxy group.
- alkylthio group examples include a methylthio group, an ethylthio group, a normal pentylthio group, an isopropylthio group, and a cyclohexylthio group.
- the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- Alkenyl groups are [3-1] to [3-3]:
- a specific example of the polymer of the formula (1) used in the present invention is the formula (4), and the polymer of the formula (4) is obtained by reacting a diepoxy compound with a dicarboxylic acid.
- the dicarboxylic acid forms a partial structure of the formula (2) and the formula (3), and a linear aliphatic dicarboxylic acid is exemplified above as a specific example.
- Diepoxy compounds are for example [4 1] to [4 16]:
- Examples of the polymer of the formula (4) obtained by reacting a dicarboxylic acid and a diepoxy compound are, for example, [5-1] to [5-25]:
- the polymer of the formula (4) has a repeating unit m of 3 to: L000, preferably 3 to 250, preferably 10 to 100, and a weight average molecular weight of 1000 to 1000000, preferably ⁇ 1000 to 100000.
- the preferred ⁇ is 2000-50000.
- Both ends of the polymer of formula (4) are a hydroxyl group or a carboxyl group, the carboxyl group side is a carboxylic acid force, and the epoxy side is a hydroxyl group.
- the polymer of the formula (4) the polymer of the formula (15) and the polymer of the formula (16) can be preferably used as more specific polymers, and the polymer of the formula (15) is particularly preferable! /.
- the polymer of the formula (14) can be used as the polymer of the formula (1).
- the polymer of formula (14) it is possible to use the same Q as Q in formula (4).
- n is an integer of 0-2.
- R can be the same as R in formula (3), b is
- the repeating unit m of the polymer of formula (14) is 3 to 1000, preferably 3 to 250, preferably 10 to 100, and the weight average molecular weight is 1000 to 1000000, good Better ⁇ is 1000 ⁇ 100,000, preferably ⁇ is 2000 ⁇ 50000.
- Both ends of the polymer of formula (14) are a hydroxyl group or a carboxyl group, the carboxyl group side is a carboxylic acid, and the epoxy side is a hydroxyl group.
- the polymers of formula (14) are [6-1] to [6-3]:
- the diepoxy compound and the dicarboxylic acid have a polymer chain that extends in two dimensions by a condensation reaction. These are preferably a bifunctional epoxy compound and a carboxylic acid. When trifunctional compounds are used, gelling may occur.
- the dicarboxylic acid is an aliphatic dicarboxylic acid
- the dicarboxylic acid is an aromatic dicarboxylic acid in the reaction of a diepoxy compound with a dicarboxylic acid, use either a quaternary phosphor salt or a quaternary ammonium salt. Can do.
- Quaternary phosphor used as a catalyst in the reaction of diepoxy compound with dicarboxylic acid The salt is of formula (17):
- R, R 1, R 2, and R are each an alkyl group having 1 to 10 carbon atoms or
- P represents a phosphorus atom, ⁇ or anion
- R
- R 1, R 2, and R 3 are each bonded to the phosphorus atom by a C—P bond.
- R 1, R 2, R 3 and R 4 are alkyl groups having 1 to 18 carbon atoms or aryl
- the other organic group is preferably an alkyl group having 1 to 10 carbon atoms.
- the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, and an octyl group
- the aryl group is preferably a full group or a substituted full group, for example.
- An example is a tolyl group.
- the remaining one organic group is preferably an alkyl group having 1 to 18 carbon atoms.
- Anions (Y—) can also be halogen ions such as chlorine ions (C1), bromine ions (Br—), iodine ions ( ⁇ ), carboxylates (1 C OO—), sulfonates (—SO—), An acid group such as alcoholate (—O—) can be mentioned.
- the compound of the formula (16) can be obtained as a commercial product.
- halogenated tetraalkyl phosphines such as halogenated tetra- n -butyl phosphate and halogenated tetra- n -propyl phosphorous.
- halogenated trialkyl monobenzil phosphors such as halogenated triethyl monobenzil phosphorous, etc.
- halogenated triphenyl monomethyl phosphate halogenated triphenyl monophenyl phosphorous, etc.
- Halogenated triphenyl monoalkyl phosphate halogenated triphenyl monobenzyl phosphate, halogenated tetraphenyl phosphate, halogenated tritolyl monoaryl phosphate, or halogenated tritolyl monoalkyl Phospho-um (norogen atom is chlorine atom or bromine atom).
- halogenated triphenyl monoalkyl phosphors such as halogenated triphenyl monomethyl phosphate, halogenated triphenyl monoethyl phosphor, etc., halogenated triphenyl monobenzyl phosphor, etc.
- Halogenated tritolyl monoaryl phosphorous such as halogenated triphenyl monoaryl phosphorous and halogenated tritolyl monoaryl phosphorous
- a halogenated tolyl monoalkyl phosphorous such as litryl monomethyl phosphorous (halogen atom is a chlorine atom or a bromine atom) is preferred.
- Reactivity of halogenated triphenyl monoalkyl phosphor is higher than that of halogenated tetraalkyl phosphor.
- triphenyl monoethyl phosphate bromide is preferred.
- the quaternary ammonium salt used as a catalyst for the reaction between the diepoxy compound and the dicarboxylic acid is represented by the formula (18):
- R, R, R and R are carbon atoms of 1
- the three organic groups are preferably alkyl groups having 1 to LO carbon atoms, and the remaining one organic group is preferably an aryl group having 6 to 14 carbon atoms.
- the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, and an octyl group.
- the aryl group is preferably, for example, a phenyl group or a substituted phenyl group.
- An example is a tolyl group.
- Anions (Y—) can be chlorine ions (C1—), bromine ions (Br—), halogen ions such as iodine ions ( ⁇ ), carboxylates (one COO—), sulfonates (one SO—), alcoholates ( I O-)
- quaternary ammonium salts are, for example, halogenated tetraalkyl ammonium, halogenated tetraethyl ammonium, halogenated tetrabutyl ammonium, halogenated trioctyl monomethyl ammonium, and the like, Halogenated trialkyl monoaryl ammonia, halogenated triethyl monobenzene ammonium, halogenated tributylbenzyl ammonium, halogenated trimethylbenzyl ammonium, etc. Examples thereof include halogenated triphenyl monoalkyl ammonium such as halogenated triphenyl ammonium and halogenated trityl monomethyl ammonium.
- triethylmonochloroammonium chloride, triethylmonochloroammonium bromide, and the like which are preferably trialkylmonochloroammonium halides, are exemplified.
- a diepoxy compound and a dicarboxylic acid Force at which the reaction is carried out This reaction is carried out in a solvent containing a quaternary phosphoric acid salt or a quaternary ammonium salt at a temperature of 50 to 200 ° C. in a nitrogen stream for 0.5 to 48 hours. This reaction is performed.
- the starting diepoxy compound and dicarboxylic acid in the solvent are used in a total mass of 5 to 80% by mass.
- solvent used in this reaction examples include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, benzene, toluene, xylene, ethyl lactate, butyl lactate, N-methylpyrrolidone, cyclohexane, and ⁇ -butyllatatatone. These can be used alone or as a mixed solvent of two or more.
- the reaction solvent containing the produced polymer contains a halogenated quaternary phosphorous salt or a halogenated quaternary ammonium salt used as a catalyst.
- a halogenated quaternary phosphor salts and halogenated quaternary ammonium salts are produced from the reaction product by alternately contacting the reaction solvent with a cation exchange resin and an anion exchange resin. Halogenated quaternary phosphorous salts and halogenated quaternary ammonium salts can be removed.
- Examples of the cation exchange resin used here include a trade name Amberlite 15JWE Koji (manufactured by Organo Co., Ltd.) and a trade name HCR (manufactured by Muromachi Chemical Co., Ltd.).
- the product name is 550 ⁇ (Muromachi Chemical Co., Ltd.) and the product name is 650C (Muromachi Chemical Co., Ltd.).
- the resist underlayer 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 melamine compounds and substituted urea compounds having a cross-linking substituent such as methylol group and methoxymethyl group.
- it is a compound such as methoxymethyl isopropyl glycoluril, or methoxymethylated melamine, for example, tetramethoxymethyldarlicururyl, tetrabutoxymethyl glycoluril, or hexamethoxymethylmelamine.
- crosslinkable compounds such as tetramethoxymethylurea and tetrabutoxymethylurea.
- These crosslinkable compounds can cause a crosslinking reaction by self-condensation. Further, it can cause a crosslinking reaction with a hydroxyl group in the polymer used in the present invention. And by such a crosslinking reaction The resist underlayer film to be formed becomes strong. And it becomes a resist underlayer film with low solubility in an organic solvent. Only one kind of the crosslinkable compound may be used, or two or more kinds may be used in combination.
- the content thereof is, for example, 1 to 50% by mass or 10 to 40% by mass in the solid content.
- the resist underlayer film forming composition of the present invention may contain an acid compound, an acid generator, or a combination thereof.
- the acid compound include sulfonic acid compounds such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, and pyridinium-p-toluenesulfonate, salicylic acid, sulfosalicylic acid, citrate, benzoic acid, and hydroxy Examples thereof include carboxylic acid compounds such as benzoic acid.
- the acid generator include 2
- odonium salt acid generators such as diphenyl rhodium hexafluorophosphate, diphenyl rhodium trifluoromethanesulfonate, and bis (4 tert butylphenol) rhodium trifluoromethanesulfonate
- sulfo-sulfate-based acid generators such as trisulfo-sulfahexafluoroantimonate and triphenylsulfo-mu-trifluoromethanesulfonate.
- a sulfonic acid compound is preferably used, and as the acid generator, a iodine salt acid generator or a sulfo salt acid generator is preferably used.
- the acid compound and the acid generator may be used alone or in combination of two or more.
- the content of the acid compound is, for example, 0.001 to 5% by mass in the solid content, or 0.005 to 1 % By mass.
- the acid generator in the solid content is, for example, 0.001 to 5% by mass, or 0.001 to 1% by mass.
- the resist underlayer film forming composition of the present invention can contain optional components such as other polymers, light-absorbing compounds, rheology modifiers, and surfactants, if necessary.
- the other polymer include polymers produced from addition polymerizable compounds. Addition polymerizable compounds such as acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, methacrylamide compounds, vinyl compounds, styrene compounds, maleimide compounds, maleic anhydride, and acrylonitrile Addition polymerization polymer produced from the product. Other examples include polyester, polyamide, polyimide, polyamic acid, polycarbonate, polyether, phenol novolak, cresol novolak, and naphthol novolak. When other polymers are used, the amount used is, for example, 0.1 to 40% by mass in the solid content.
- the light-absorbing compound is not particularly limited as long as it has high absorptivity with respect to light in the photosensitive characteristic wavelength region of the photosensitive component in the photoresist layer provided on the resist underlayer film. can do.
- Examples of the light-absorbing compound include benzophenone compounds, benzotriazole compounds, azo compounds, naphthalene compounds, anthracene compounds, anthraquinone compounds, triazine compounds, triazine trione compounds, quinoline compounds. Things can be used. Naphthalene compounds, anthracene compounds, triazine compounds, and triazine trione compounds are used.
- Specific examples include, for example, 1-naphthalene carboxylic acid, 2-naphthalene carboxylic acid, 1 naphthol, 2-naphthol, naphthyl acetic acid, 1 hydroxy 2 naphthalene strength norebonic acid, 3 hydroxy 2 naphthalene strength nolevonic acid, 3, 7 dihydro Xy 2 naphthalene carboxylic acid, 6 bromo-2 hydroxy naphthalene, 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-hydroxyanthracene 1, 2, 3 Anthracentriol, 9-Hydroxymethylanthracene, 2, 7, 9 Anthracentriol, Benzoic acid, 4 Hydroxybenzoic acid, 4 Bromobenzoic acid, 3 Eodobenz
- Examples of the rheology modifier include dimethyl phthalate, jetyl phthalate, and diisophthalate.
- Phthalic compounds such as butyl phthalate, dihexyl phthalate, butyl isodecyl phthalate, adipic acid compounds such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate, dinormal butylmer
- Mention may be made of maleic acid compounds such as acrylate, jetyl malate and dino-malarate, oleic acid compounds such as methyl oleate, butyrate and tetrahydrofurfurolate, and stearic acid compounds such as normal butyl stearate and glyceryl stearate. it can.
- the amount used thereof is, for example, 0.001 to 10% by mass in the solid content.
- 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, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate Sorbitan fatty acid esters such as sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Non-ionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, Product names F-top EF301
- the solvent used in the resist underlayer film forming composition of the present invention can be used without any particular limitation as long as it is a solvent capable of dissolving the above-mentioned solid content.
- solvents include, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cetyl sorb acetate, cetyl solv acetate, diethylene glycol monomethinoatenoate, diethyleneglycolenomethenoatenoatere.
- the resist underlayer film of the present invention is applied to a semiconductor substrate (for example, silicon Z dioxide-silicon coated substrate, silicon nitride substrate, glass substrate, ITO substrate, etc.) by an appropriate coating method such as a spinner or a coater.
- the resist composition is applied and then fired to form a resist underlayer film.
- medium strength of firing temperature of 80 ° C to 250 ° C and firing time of 0.3 to 60 minutes is appropriately selected.
- the firing temperature is 130 ° C to 250 ° C
- the firing time is 0.5 to 5 minutes.
- the film thickness of the resist underlayer film to be formed is, for example, 0.01 to 3. O / zm, preferably, for example, 0.03 to: L, or 0.03 to 0. Yes, or from 0.05 to 0.
- a photoresist layer is formed on the resist underlayer film of the present invention.
- the 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 resist underlayer film.
- the photoresist applied and formed on the resist underlayer 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.
- Proc. SPIE Vol. 3999, 330—334 (2000)
- Proc. SPIE Vol. 3999, 357—364 (2000)
- Proc. SPIE Vol. 3999, 36 5-374 (2000)
- fluorine-containing atomic polymer photoresists as described in (1).
- 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 heating (PEB) may 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 tetramethyl ammonium.
- alkaline aqueous solutions such as aqueous solutions of quaternary ammonium hydroxide such as choline and amine aqueous solutions such as ethanolamine, propylamine, and ethylenediamine.
- a surfactant or the like can be added to these developers.
- the temperature is 5 to 50 ° C
- the time is 10 to 300 seconds.
- a resist using the photoresist pattern thus formed as a protective film, a resist
- the lower layer film is removed and the semiconductor substrate is processed.
- the resist underlayer film can be removed by using tetrafluoromethane, perfluorocyclobutane (CF 3), perfluoropropane (CF 3),
- gases such as rifluoromethane, carbon monoxide, argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, nitrogen trifluoride and chlorine trifluoride.
- a flat film or a gap fill material layer may be formed before the resist underlayer film of the present invention is formed on the semiconductor substrate.
- a flat film or a gap fill material layer is formed.
- the semiconductor substrate to which the resist underlayer film forming composition of the present invention is applied may have an inorganic resist underlayer film formed on its surface by a CVD method or the like.
- a resist underlayer film can also be formed.
- the resist underlayer film of the present invention has a detrimental effect on the substrate of the layer for preventing the interaction between the substrate and the photoresist, the material used for the photoresist or the material generated upon exposure to the photoresist.
- a layer having a function of preventing, a layer having a function of preventing the diffusion of the material generated from the substrate during heating and baking into the upper layer photoresist, and a noria layer for reducing the voiding effect of the photoresist layer by the semiconductor substrate dielectric layer It is also possible to use as such.
- the resist underlayer film formed from the resist underlayer film forming composition is applied to a substrate on which via holes used in the dual damascene process are formed, and can be used as a filling material that can fill the holes without any gaps. It can also be used as a planarizing material (gap fill material) for planarizing the surface of an uneven semiconductor substrate.
- Monoallyl diglycidyl isocyanuric acid 10 Og and 5.4 g of tartaric acid, 0.7 g of triphenyl monoethyl phosphomubromide as a catalyst was dissolved in 37.5 g of propylene glycol monomethyl ether, and the reaction solution was heated to 120 ° C. And stirred for 24 hours under a nitrogen atmosphere. When the GPC analysis of the obtained reaction product was conducted, the weight average molecular weight was 6900 in terms of standard polystyrene.
- Monoallyl diglycidyl isocyanuric acid 10 Og and 4.8 g of malic acid, 0.7 g of triphenyl monoethyl phosphomum bromide as a catalyst were dissolved in 36 lg of propylene glycol monomethyl ether, and then the reaction solution was stirred at 120 ° C. Warm to C and stir under nitrogen for 24 hours. When the GPC analysis of the obtained reaction product was conducted, the weight average molecular weight was 4000 in terms of standard polystyrene.
- Monoallyl diglycidyl isocyanuric acid 10 Og and 6.6 g of hydroxyisophthalic acid and 0.4 g of monobenzyltriethyl ammonium chloride as catalyst were dissolved in 39.6 g of propylene glycol monomethyl ether, The reaction was warmed to 120 ° C and stirred for 24 hours under a nitrogen atmosphere. When the GPC analysis of the obtained reaction product was conducted, the weight average molecular weight was 13700 by standard polystyrene conversion.
- Monoallyl diglycidyl isocyanuric acid 5 Og and 3.0 g of phthalic acid, and 0.2 g of monophenyltriethylammonium chloride as a catalyst were dissolved in propylene glycol monomethyl ether 1 9. lg. The mixture was heated to ° C and stirred for 24 hours under a nitrogen atmosphere. When the GPC analysis of the obtained reaction product was conducted, the weight average molecular weight was 1800 in standard polystyrene conversion.
- Example 5 The same procedure as in Example 1 was performed except that the polymer obtained in Synthesis Example 5 was used instead of the polymer obtained in Synthesis Example 1.
- the solutions of the resist underlayer film forming compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 2 were each applied onto a semiconductor substrate (silicon wafer) with a spinner. On the hot plate, it was baked at 205 ° C for 1 minute to form a resist underlayer film (thickness: 0.10 m). This resist underlayer film was immersed in a solvent (ethyl acetate and propylene glycol monomethyl ether acetate) used for a photoresist, and it was confirmed that it was insoluble in the solvent.
- a solvent ethyl acetate and propylene glycol monomethyl ether acetate
- the resist underlayer film forming composition solutions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were applied onto a silicon wafer by a spinner. Baking was performed at 205 ° C for 1 minute on a hot plate to form a resist underlayer film (film thickness 0.06 m). These resist underlayer films were measured for refractive index (n value) and attenuation coefficient (k value) at a wavelength of 193 nm using a spectroscopic ellipsometer (manufactured by JA Woollam, VUV-VASE VU-302). The evaluation results are shown in Table 1.
- the resist underlayer film forming composition solutions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were applied onto a silicon wafer using a spinner. Bake on a hot plate at 205 ° C for 1 minute, A resist underlayer film was formed. And using Nihon Scientific RIE system ES401, dry etching rate (unit: CF) as the dry etching gas.
- the amount of decrease in film thickness per hour was measured.
- a photoresist solution (product name: PAR710, manufactured by Sumitomo Chemical Co., Ltd.) is applied onto a silicon wafer using a spinner and heated on a hot plate at 90 ° C for 1 minute to form a photoresist layer. did. And using Nihon Scientific RIE system ES401, dry etching rate was measured under the condition of using CF as dry etching gas.
- the resist underlayer film obtained from the resist underlayer film forming composition of the present invention has a sufficiently effective refractive index and attenuation with respect to 193 nm light. The fact that it has a coefficient contributed. It was also found that it has a large dry etching rate selectivity relative to the photoresist. Therefore, the time required for removing the resist underlayer film by dry etching is shortened. It is possible to reduce the thickness of the photoresist layer accompanying the removal of the resist underlayer film by dry etching, and it is preferable to suppress the phenomenon.
- a commercially available photoresist solution CFSR (trade name: AR1221J) is applied with a spinner and heated on a hot plate at 130 ° C for 90 seconds to form a photoresist film (film thickness). 0.25 m) was formed.
- the photoresist line width and the width between the lines after development was 0.09 m, ie 0.08 mLZS (dense line), and exposure was performed through a mask set to form nine such lines. Thereafter, the film was heated after exposure for 90 seconds at 130 ° C. on a hot plate. After cooling, the film was developed with a 0.26N aqueous solution of tetramethylammonium hydroxide as a developing solution in an industrial standard 60 second single paddle process.
- the focus depth margin was determined as follows. That is, the exposure was performed while shifting the focus position up and down by 0.1 m with respect to the optimum focus position, and a resist pattern was formed by subsequent development processing. Of the nine photoresist lines to be formed, 5 or more lines were formed, and the case where the number of remaining lines was 4 or less was rejected.
- the focus depth margin was defined as the width above and below the shift in focus position at which a pass result could be obtained. As a result, when the resist underlayer film forming compositions obtained in Examples 1 to 5 were used, the force depth margin was 0.7 or more.
- Example 6 To 1 Og of the solution containing 2 g of the polymer obtained in Synthesis Example 1, 38 g of propylene dallicol monomethyl ether was added to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 m, and further filtered using a polyethylene microfilter having a pore size of 0.05 m, so that the resist underlayer film forming composition containing only the polymer is obtained. A solution was prepared.
- a resist underlayer film forming composition was obtained in the same manner as in Example 6 except that the polymer obtained in Synthesis Example 3 was used instead of the polymer obtained in Synthesis Example 1.
- a resist underlayer film forming composition was obtained in the same manner as in Example 6 except that the polymer obtained in Synthesis Example 4 was used instead of the polymer obtained in Synthesis Example 1.
- a resist underlayer film forming composition was obtained in the same manner as in Example 6 except that the polymer obtained in Synthesis Example 5 was used instead of the polymer obtained in Synthesis Example 1.
- a resist underlayer film forming composition was obtained in the same manner as in Comparative Example 3 except that the polymer obtained in Synthesis Example 7 was used instead of the polymer obtained in Synthesis Example 6.
- the resist underlayer film formed only from the polymer obtained from the resist underlayer film forming composition of the present invention has an effect of preventing mixing with the resist solvent even if it does not contain a crosslinking agent.
- the polymer of Example 6 it became apparent that a resist underlayer film without mixing with the resist was obtained even if it did not contain any crosslinking agent. Therefore, it is not necessary to contain a crosslinkable compound and an acid compound or an acid generator for crosslinking the crosslinkable compound and the polymer.
- the crosslinkable compound, the acid compound and the acid generator are low molecular weight compounds, and the resist underlayer film forming composition containing them is formed by applying the resist underlayer film forming composition to a substrate and forming a resist underlayer film by heat curing. A part of the material is scattered as a sublimation product and adheres to the inside of the chamber. When it cools, it falls onto the substrate, and the fallen product becomes a foreign substance on the substrate and may cause a problem.
- the resist underlayer film that does not cause mixing with the overcoated photoresist solution even if it does not contain a crosslinkable compound, an acid compound, and an acid generator as described above has a problem caused by the above foreign matter. Can be solved.
- the photoresist formed on the semiconductor substrate especially ArF excimer laser (wavelength 193nm) from the substrate
- Lithographic resist that can be used as an underlayer anti-reflection film that reduces reflection of light, a flattening film for flattening an uneven semiconductor substrate, a film that prevents contamination of photoresist by substances generated from the semiconductor substrate during heating and baking, etc.
- the present invention can be used for an underlayer film and a resist underlayer film forming composition for forming the underlayer film.
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Abstract
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EP07745397A EP2042927B1 (en) | 2006-06-19 | 2007-06-15 | Composition containing hydroxylated condensation resin for forming film under resist |
KR1020087028294A KR101423056B1 (ko) | 2006-06-19 | 2007-06-15 | 수산기 함유 축합계 수지를 함유하는 레지스트 하층막 형성조성물 |
CN200780022550.1A CN101473270B (zh) | 2006-06-19 | 2007-06-15 | 含有具有羟基的缩合系树脂的形成抗蚀剂下层膜的组合物 |
JP2008522432A JP5041175B2 (ja) | 2006-06-19 | 2007-06-15 | 水酸基含有縮合系樹脂を含有するレジスト下層膜形成組成物 |
US12/308,566 US8445175B2 (en) | 2006-06-19 | 2007-06-15 | Composition containing hydroxylated condensation resin for forming resist underlayer film |
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Also Published As
Publication number | Publication date |
---|---|
EP2042927A4 (en) | 2010-01-06 |
EP2042927B1 (en) | 2012-03-07 |
TWI490654B (zh) | 2015-07-01 |
US20090317740A1 (en) | 2009-12-24 |
EP2042927A1 (en) | 2009-04-01 |
TW200815925A (en) | 2008-04-01 |
US8445175B2 (en) | 2013-05-21 |
JP5041175B2 (ja) | 2012-10-03 |
KR101423056B1 (ko) | 2014-07-25 |
CN101473270B (zh) | 2014-08-06 |
KR20090023353A (ko) | 2009-03-04 |
JPWO2007148627A1 (ja) | 2009-11-19 |
CN101473270A (zh) | 2009-07-01 |
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