WO2018186310A1 - 光架橋基を有するポリエーテル樹脂を含む段差基板被覆組成物 - Google Patents
光架橋基を有するポリエーテル樹脂を含む段差基板被覆組成物 Download PDFInfo
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- WO2018186310A1 WO2018186310A1 PCT/JP2018/013894 JP2018013894W WO2018186310A1 WO 2018186310 A1 WO2018186310 A1 WO 2018186310A1 JP 2018013894 W JP2018013894 W JP 2018013894W WO 2018186310 A1 WO2018186310 A1 WO 2018186310A1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4043—(I) or (II) containing oxygen other than as phenol or carbonyl group
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
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- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2012—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
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- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
Definitions
- the present invention relates to a stepped substrate coating composition for forming a planarized film on a substrate having a step by photocrosslinking, and a method for producing a planarized laminated substrate using the stepped substrate coating composition.
- Resist underlayer film-forming composition comprising a polymer having an epoxy group or oxetane group in the side chain and a photocationic polymerization initiator, or a resist comprising a polymer having an ethylenically unsaturated bond capable of radical polymerization and a photoradical polymerization initiator
- An underlayer film forming composition is disclosed (see Patent Document 1).
- a resist underlayer film forming composition comprising a silicon-based compound having a reactive group capable of cationic polymerization such as an epoxy group or a vinyl group, a cationic photopolymerization initiator, and a radical photopolymerization initiator (patent) Reference 2)
- a crosslinkable functional group for example, a hydroxyl group
- a pattern formed on a substrate for example, In order to fill the hole or trench structure, the crosslinking reaction proceeds during heating, resulting in an increase in viscosity, and the pattern filling property becomes a problem. And since thermal shrinkage occurs due to degassing, flatness becomes a problem.
- a resist underlayer film forming composition containing a polymer having a reactive group capable of cationic polymerization such as an epoxy group or a vinyl group and an acid generator light irradiation and heating are performed. At that time, thermal shrinkage due to degassing also occurs, and flatness becomes a problem.
- the photocurable stepped substrate coating composition of the present invention is a film having a flatness capable of forming a coating film by photocuring which has high pattern filling properties and does not cause degassing or thermal shrinkage, and is irradiated with light.
- a stepped substrate coating composition capable of later forming a highly heat-resistant coating on a substrate.
- the formula (1) [In the formula (1), A 1 , A 2 and A 3 each independently represent an aromatic ring having 6 to 100 carbon atoms which may contain a hetero atom or a hetero atom.
- R 1 represents an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, an alkynylene group having 1 to 10 carbon atoms, an arylene group having 6 to 40 carbon atoms
- the alkylene group, alkenylene group, alkynylene group and arylene group may be optionally substituted with one or more cyano groups and / or one or more hydroxyl groups), an oxygen atom, A carbonyl group, a sulfur atom, —C (O) —O—, —C (O) —NR a
- a photocurable stepped substrate coating composition comprising a polymer comprising a unit structure of
- a 1 represents formula (1-1) or formula (1-2): (However, in the formulas (1-1) and (1-2), each T 1 is independently a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or carbon.
- Arylalkyl group having 7 to 28 atoms, alkylcarbonyl group having 2 to 10 carbon atoms, alkylcarbonyloxy group having 2 to 10 carbon atoms, alkylcarbonylamino group having 2 to 10 carbon atoms, 7 to 7 carbon atoms 28 is an aryloxyalkyl group, an organic group consisting of an alkoxy group having 1 to 6 carbon atoms or a combination thereof, q is an integer of 2 to 6, and when q is 2, T 2 is a single bond, Or a divalent hydrocarbon group having 1 to 10 carbon atoms which may have a hydroxyl group, or an aryl having 7 to 28 carbon atoms which may have a hydroxyl group In the case where q is 3 to 6, T 2 may have a hydroxyl group, a tri to hexavalent hydrocarbon group having 1 to 10 carbon atoms, or a hydroxyl group.
- a trivalent to hexavalent arylalkyl group having 7 to 28 carbon atoms m is an integer of 1 to 7
- n is an integer of 0 ⁇ n ⁇ 7-m
- the formula (1-2 two T 2 in), taken together, may form a ring
- p is two hydroxyl groups among the m ⁇ q pieces of hydroxyl groups in the polynuclear phenol represented by an integer of 0 or 1.
- a bond that binds to two O atoms in A 1 and the remaining hydroxyl group of m ⁇ q hydroxyl groups in the polynuclear phenol and / or a hydrogen atom of T 2 binds to B 1 in A 1 becomes a hand, however, combined with the B 1 That the total number of bonds is to be the n1, photocurable stepped substrate coating composition according to the first aspect,
- a 1 is a group derived from tri (hydroxyphenyl) methane, a group derived from tetrakis (hydroxyphenyl) ethane, or a group derived from tetrakis (hydroxyphenyl) -p-xylene,
- a 2 and A 3 are groups derived from a benzene ring or a naphthalene ring,
- the photocurable stepped substrate coating composition according to any one of the first to third aspects, wherein X is a carbonyl group,
- the photocurable stepped substrate coating composition according to the first aspect wherein the unit structure of the formula (1) is a polymer including a unit structure in which n1 is 1 or 2, and n2 and n3 are 0,
- the polymer is further added to the unit structure of the formula (1) in the formula (3) (In Formula (3), A 4 and A 5 each represent an aromatic ring having 6 to 48 carbon atoms which may contain a hetero atom, or 6 to 48 carbon atoms which may contain a hetero atom.
- the photocurable stepped substrate coating according to any one of the first to seventh aspects, wherein the stepped substrate coating composition is a resist underlayer film forming composition used in a lithography process for manufacturing a semiconductor device.
- the stepped substrate coating composition is a resist underlayer film forming composition used in a lithography process for manufacturing a semiconductor device.
- a ninth aspect includes a step (i) of applying the photocurable stepped substrate coating composition according to any one of the first to eighth aspects to a stepped substrate, and an exposing step (ii). Manufacturing method of coated substrate,
- a tenth aspect is the ninth aspect in which the step (ia) is performed in which the photocurable stepped substrate coating composition in the step (i) is applied and then heated at a temperature of 70 to 400 ° C. for 10 seconds to 5 minutes.
- the method for producing a coated substrate according to the eighth aspect or the tenth aspect wherein the exposure wavelength in the step (ii) is 150 nm to 248 nm,
- a method of manufacturing a coated substrate according to any one of the ninth aspect to eleventh aspect exposure amount is 10 mJ / cm 2 to 3000 mJ / cm 2 step (ii),
- the substrate has an open area (non-pattern area) and a pattern area of DENCE (dense) and ISO (coarse), and the aspect ratio of the pattern is 0.1 to 10,
- the method for manufacturing a coated substrate according to the thirteenth aspect in which a bias (application step) between the open area and the pattern area is 1 to 50 nm,
- a method of manufacturing a semiconductor device including a step of forming a resist pattern by electron beam irradiation and development, a step of etching the lower layer film with the resist pattern, and a step of processing a semiconductor substrate with the patterned lower layer film, and
- a step of forming a lower layer film on the substrate having a step with the photocurable stepped substrate coating composition according to any one of the first to eighth aspects, and a step of forming a hard mask thereon Further, a step of forming a resist film thereon, a step of forming a resist pattern by light and electron beam irradiation and development, a step of etching a hard mask with the resist pattern, and etching the lower layer film with a patterned hard mask
- a method of manufacturing a semiconductor device including a step of processing a semiconductor substrate with a patterned underlayer film.
- the present invention it is applied onto a substrate and optionally filled into a pattern by reflow by heating.
- a flat film is formed regardless of an open area (non-pattern area) or a pattern area of DENCE (dense) and ISO (coarse).
- species is formed by the light irradiation of the unsaturated bond of carbon and carbon.
- the stepped substrate coating composition of the present invention does not contain a crosslinking agent and an acid catalyst, and the stepped substrate coating film (planarized film) formed by applying the stepped substrate coating composition has an unsaturated bond between carbon and carbon. It can bridge
- the stepped substrate coating film (flattened film) by the stepped substrate coating composition of the present invention does not cause a crosslinking reaction by a crosslinking agent and an acid catalyst during thermal reflow, and the subsequent photocrosslinking is a photoreaction without degassing. Therefore, heat shrinkage does not occur. Thereby, the filling property to the pattern and the planarization property after the filling are satisfied at the same time, and an excellent planarization film can be formed.
- the photocurable stepped substrate coating composition of the present invention is a film having a flatness capable of forming a coating film by photocuring which has high pattern filling properties and does not cause degassing or thermal shrinkage, and is irradiated with light. It is a stepped substrate coating composition that can later form a highly heat-resistant coating on a substrate. Even when a high-temperature hard mask layer is formed on the photocurable stepped substrate coating film, it has sufficient heat resistance.
- the present invention is a photocurable stepped substrate coating composition containing a polymer containing the unit structure of formula (1).
- a 1 , A 2 and A 3 each independently represent an aromatic ring having 6 to 100 carbon atoms which may contain a hetero atom, or may contain a hetero atom.
- a hetero atom includes a nitrogen atom and an oxygen atom.
- the hydrocarbon group can be a hydrocarbon group derived from the following alkyl group.
- aromatic ring having 6 to 100 carbon atoms examples include benzene ring, biphenyl ring, terphenylene ring, fluorene ring, naphthalene ring, anthryl ring, pyrene ring, carbazole ring, and indole ring.
- R 1 represents an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, an alkynylene group having 1 to 10 carbon atoms, an arylene group having 6 to 40 carbon atoms (this The alkylene group, alkenylene group, alkynylene group and arylene group may be optionally substituted with one or more cyano groups and / or one or more hydroxyl groups), oxygen atom, carbonyl A group consisting of a group, a sulfur atom, —C (O) —O—, —C (O) —NR a —, —NR b — or a combination thereof, and R 2 represents a hydrogen atom or a carbon atom having 1 to 10 alkyl groups are shown, and a dotted line shows a bond with A 1 , A 2 , or A 3 .
- R 1 an oxygen atom, a carbonyl group, a sulfur atom, —C (O) —O—, —C (O) —NR a —, and —NR b — are not bonded to each other.
- a 1 can represent, for example, a group derived from a polynuclear phenol represented by formula (1-1) or formula (1-2).
- the polynuclear phenol has at least 3 hydroxyl groups, preferably 3 to 6, or 3 to 5, or 3 to 4 hydroxyl groups.
- the number of hydroxyl groups possessed by the polynuclear phenol is intended to be m ⁇ q.
- a 1 is a group obtained by removing two hydroxyl groups from m ⁇ q hydroxyl groups of the polynuclear phenol.
- the unit structure of the formula (1) is a polymer formed by dehydrohalogenation reaction of two hydroxyl groups of m ⁇ q hydroxyl groups of polynuclear phenol with a dihalogenated diaryl group containing an X moiety. It can be formed by introducing the functional group of formula (2) into the remaining hydroxyl groups.
- the hydroxyl group in the polymer can be subjected to an addition reaction with an unsaturated group-containing epoxy compound such as allyl glycidyl ether, glycidyl acrylate, or glycidyl methacrylate to form a polymer having a unit structure of formula (1).
- an unsaturated group-containing epoxy compound such as allyl glycidyl ether, glycidyl acrylate, or glycidyl methacrylate
- the hydroxyl group in the polymer can be reacted with an allyl halide (for example, allyl bromide, allyl chloride) to form a polymer having a unit structure of formula (1).
- an allyl halide for example, allyl bromide, allyl chloride
- the hydroxyl group in the polymer is epoxidized with an epoxy compound such as epichlorohydrin and then reacted with an unsaturated carboxylic acid corresponding to formula (2) (for example, acrylic acid or methacrylic acid) to form a unit structure of formula (1) Can be formed.
- an epoxy compound such as epichlorohydrin
- an unsaturated carboxylic acid corresponding to formula (2) for example, acrylic acid or methacrylic acid
- each T 1 independently represents a halogen group, an alkyl group having 1 to 10 carbon atoms, a carbon atom
- An organic group comprising a carbonylamino group, an aryloxyalkyl group having 7 to 28 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a combination thereof
- q represents an integer of 2 to 6, in some cases
- T 2 is a single bond, or a hydrocarbon group having 1 to 10 carbon atom divalent hydroxyl groups may have a or may have a hydroxyl group good Divalent an aryl alkyl group having
- Two hydroxyl groups among the m ⁇ q pieces of hydroxyl groups in the polynuclear phenol of the formula (1-1) or formula (1-2) becomes a bond that binds to two O atoms in A 1, the Of the mxq hydroxyl groups in the polynuclear phenol, the remaining hydroxyl group and / or the hydrogen atom of T 2 becomes a bond to B 1 in A 1 , provided that the number of bonds to bond to B 1 The total is n1.
- the polynuclear phenol can be exemplified as follows.
- the polymer of formula (1) is a group wherein A 1 is derived from tri (hydroxyphenyl) methane, a group derived from tetrakis (hydroxyphenyl) ethane, or a group derived from tetrakis (hydroxyphenyl) -p-xylene. And A 2 and A 3 preferably have a group derived from a benzene ring or a naphthalene ring, a group having a tri (hydroxyphenyl) methane structure, a group having a tetrakis (hydroxyphenyl) ethane structure, or a tetrakis Groups having the structure (hydroxyphenyl) -p-xylene are also preferred.
- X is a carbonyl group
- n1 in Formula (1) is 1 or 2
- the polymer whose n2 and n3 are 0 can be used.
- the stepped substrate coating composition may contain an additive such as a surfactant as necessary.
- the solids content of this composition is 0.1 to 70% by weight, or 0.1 to 60% by weight, or 0.2 to 30% by weight, or 0.3 to 15% by weight. Solid content is the content rate of all the components remove
- the polymer used in the present invention has an average molecular weight of 600 to 1000000, or 600 to 200000, or 1500 to 15000.
- the polymer can form a crosslinked structure by photoreaction of an unsaturated bond between carbon and carbon between molecules or within the molecule, but this unsaturated bond between carbon atoms, that is, an unsaturated double bond between carbon atoms.
- This unsaturated bond between carbon atoms that is, an unsaturated double bond between carbon atoms.
- alkyl group examples include alkyl groups having 1 to 10 carbon atoms, such as methyl group, ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl, t-butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl Group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n- Propyl group, cyclopentyl group, 1-methyl-cyclobutyl group, 2-methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,2-
- Examples of the alkylcarbonyl group having 2 to 10 carbon atoms include groups in which each of the alkyl groups having 1 to 9 carbon atoms listed above is bonded to the carbonyl group, and alkylcarbonyloxy having 2 to 10 carbon atoms.
- Examples of the group include a group in which each of the alkyl groups having 1 to 9 carbon atoms listed above is bonded to a carbonyloxy group, and examples of the alkylcarbonylamino group having 2 to 10 carbon atoms include the above-described carbonylamino group.
- an alkoxy group having 1 to 6 carbon atoms bonded to each other, and the alkoxy group having 1 to 6 carbon atoms may be an oxygen atom having 1 to 6 carbon atoms listed above. Examples include a group to which an alkyl group is bonded.
- aryl group examples include aryl groups having 6 to 40 carbon atoms, such as phenyl group, biphenyl group, terphenylene group, fluorene group, naphthyl group, anthryl group, pyrene group, and carbazole group.
- 6 to 18 aryl groups include phenyl, biphenyl, terphenylene, fluorene, naphthyl, anthryl, pyrene, and carbazole groups.
- the arylalkyl group having 7 to 28 carbon atoms among the groups in which the above alkyl group having 1 to 10 carbon atoms is substituted with the above aryl group having 6 to 18 carbon atoms, the number of carbon atoms is Examples of the aryloxyalkyl group having 7 to 28 carbon atoms include the above alkyl group having 1 to 10 carbon atoms and the above aryl group having 6 to 18 carbon atoms. Among the groups in which the group is substituted through an oxygen atom, those having 7 to 28 carbon atoms can be mentioned.
- alkenyl group examples include alkenyl groups having 1 to 10 carbon atoms, such as ethenyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-ethenyl group, 1-butenyl group, 2-butenyl group.
- alkynyl group examples include alkynyl groups having 1 to 10 carbon atoms, such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1- Methyl-2-propynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 2-methyl-3 -Butynyl group, 3-methyl-1-butynyl group, 1,1-dimethyl-2-propynyl group, 2-ethyl-2-propynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4- Examples include a hexynyl group, a 5-hexynyl group, a 1-
- the above alkylene group is exemplified by a divalent organic group derived from the above alkyl group.
- Examples of the arylene group include divalent organic groups derived from the aryl group.
- Examples of the alkenylene group include divalent organic groups derived from the alkenyl group.
- Examples of the alkynylene group include divalent organic groups derived from the alkynyl group.
- the polymer may further contain a unit structure of the formula (3) in the unit structure of the formula (1).
- Equation (3) in, A 4 and A 5 each may carbon atoms 6 to 48 which may contain a hetero atom of the aromatic ring or aromatic ring comprise having 6 to carbon atoms which may be 48 heteroatoms
- a hetero atom includes a nitrogen atom and an oxygen atom.
- aromatic ring having 6 to 48 carbon atoms examples include benzene ring, biphenyl ring, terphenylene ring, fluorene ring, naphthalene ring, anthryl ring, pyrene ring, carbazole ring, and indole ring.
- the hydrocarbon group can be a hydrocarbon group derived from the alkyl group.
- the unit structure of the formula (1) has a molar ratio of 1: 0.1 to 1: 10 or 1: 0.5 to 1: 5 or 1: 1.
- the polymer used for this invention can be illustrated below.
- the stepped substrate coating composition of the present invention can contain a surfactant.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as rubitan monopalmitate, polyoxyethylene sorbitan monostearate, poly
- One kind selected from these surfactants may be added, or two or more kinds may be added in combination.
- the content of the surfactant is, for example, 0.01% by mass to 5% by mass with respect to the solid content obtained by removing the solvent described later from the stepped substrate coating composition of the present invention.
- ethylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, methyl cellosolve acetate, Ethyl cellosolve acetate, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monoethyl ether acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monobutyl Ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol propyl ether acetate, di
- a substrate used for manufacturing a precision integrated circuit element for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate.
- the coating is formed by baking (heating) and exposing. That is, a coated substrate is manufactured including a step (i) of applying a stepped substrate coating composition to a substrate having a step and an exposing step (ii).
- the substrate has an open area (non-pattern area) and a pattern area of DENCE (dense) and ISO (coarse), and a pattern aspect ratio of 0.1 to 10 can be used.
- the non-pattern area indicates a portion without a pattern (for example, a hole or a trench structure) on the substrate
- the DENCE (dense) indicates a portion where the pattern is densely arranged on the substrate
- the ISO (rough) indicates a pattern on the substrate.
- the pattern aspect ratio is the ratio of the pattern depth to the pattern width.
- the pattern depth is usually several hundred nm (for example, about 100 to 300 nm)
- DENCE (dense) is a place where patterns having a pattern of about several tens of nm (for example, 30 to 80 nm) are concentrated at intervals of about 100 nm.
- ISO (coarse) is a place where patterns having a pattern of several hundred nm (for example, about 200 to 1000 nm) are scattered.
- the thickness of the stepped substrate coating film (planarization film) is preferably 0.01 to 3.0 ⁇ m.
- heating can be performed after coating, and the conditions are 70 to 400 ° C., or 100 to 250 ° C. for 10 seconds to 5 minutes, or 30 seconds to 2 minutes. By this heating, the stepped substrate coating composition is reflowed to form a flat stepped substrate coating film (planarized film).
- a crosslinking agent and a crosslinking catalyst can be added when heating after coating.
- This heating is thermosetting and assists photocrosslinking, and functions effectively when the bottom of the stepped substrate coating composition cannot be sufficiently photocured, but it can be flattened due to degassing due to thermosetting.
- Thermosetting can be used in combination as long as it does not affect the decrease.
- cross-linking agent examples include melamine type, substituted urea type, and polymer type thereof.
- a cross-linking agent having at least two cross-linking substituents, methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzogwanamine, butoxymethylated benzogwanamine, Compounds such as methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or methoxymethylated thiourea.
- the condensate of these compounds can also be used.
- the addition amount of the crosslinking agent is 0.001 to 80% by mass, preferably 0.01 to 50% by mass, and more preferably 0.05 to 40% by mass with respect to the total solid content.
- An acid and / or an acid generator can be added as a catalyst for promoting the crosslinking reaction.
- p-toluenesulfonic acid trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, 5-sulfosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalene Acidic compounds such as sulfonic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, and / or 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, etc.
- a thermal acid generator such as an organic sulfonic acid alkyl ester can be blended.
- the blending amount is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, and more preferably 0.01 to 3% by mass with respect to the total solid content.
- the exposure light in step (ii) is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light), Light having a wavelength such as 172 nm (xenon excimer light) and 157 nm (F 2 laser light) is used.
- EUV extreme ultraviolet
- 248 nm KrF laser light
- 193 nm ArF laser light
- Light having a wavelength such as 172 nm (xenon excimer light) and 157 nm (F 2 laser light) is used.
- As the exposure wavelength ultraviolet light of 150 nm to 248 nm can be used, and a wavelength of 172 nm can be preferably used.
- Exposure step (ii) can be 10 mJ / cm 2 to 3000 mJ / cm 2. A photoreaction occurs at an exposure amount in this range, a crosslink is formed, and solvent resistance is produced.
- the stepped substrate coating film (planarization film) formed in this way preferably has zero bias (application step) between the open area and the pattern area, but has a range of 1 to 50 nm or 1 to 25 nm. Can be flattened.
- the bias of the open area and the DENCE area is about 15 to 20 nm, and the bias of the open area and the ISO area is about 1 to 10 nm.
- the stepped substrate coating film (planarization film) obtained by the present invention is coated with a resist film, and the resist film is exposed and developed by lithography to form a resist pattern, and the substrate is processed according to the resist pattern. It can be carried out.
- the step substrate covering film (planarization film) is a resist underlayer film, and the step substrate covering composition is also a resist underlayer film forming composition.
- a good resist pattern can be obtained by applying a resist on the resist underlayer film, irradiating with light or electron beam through a predetermined mask, developing, rinsing and drying. If necessary, heating after irradiation with light or an electron beam (PEB: Post Exposure Bake) can also be performed. Then, the resist underlayer film where the resist has been developed and removed by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- PEB Post Exposure Bake
- the exposure light of the photoresist is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light), 157 nm.
- Light having a wavelength such as (F 2 laser light) is used.
- the light irradiation can be used without particular limitation as long as it is a method capable of generating an acid from a photoacid generator in the resist, and the exposure amount is 1 to 3000 mJ / cm 2 or 10 to 3000 mJ / cm 2. Or 10 to 1000 mJ / cm 2 .
- the electron beam irradiation of an electron beam resist can be performed using an electron beam irradiation apparatus, for example.
- a resist developer having a resist underlayer film formed by using a resist underlayer film material for lithography in the present invention sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, etc.
- Inorganic alkalis primary amines such as ethylamine and n-propylamine, secondary amines such as diethylamine and di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, dimethylethanolamine and triethanolamine
- Alcohol aqueous solutions such as alcohol amines, quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, and cyclic amines such as pyrrole and piperidine can be used.
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- an organic solvent can be used as the developer.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition a step of forming a resist film thereon, a step of forming a resist pattern by light or electron beam irradiation and development, a resist pattern
- a semiconductor device can be manufactured through a step of etching the resist underlayer film and a step of processing the semiconductor substrate with the patterned resist underlayer film.
- the resist underlayer film for lithography which has a selection ratio of dry etching rates close to that of resist, is selected as a resist underlayer film for such processes, and a lower dry etching rate than resist.
- resist underlayer film for lithography having a higher ratio and a resist underlayer film for lithography having a lower dry etching rate selection ratio than a semiconductor substrate.
- a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- a process of making the resist pattern and the resist underlayer film narrower than the pattern width at the time of developing the resist at the time of the resist underlayer film dry etching has begun to be used.
- a resist underlayer film having a selectivity of a dry etching rate close to that of the resist has been required as a resist underlayer film for such a process.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- the substrate after forming the resist underlayer film of the present invention on the substrate, directly or on the resist underlayer film as needed, after forming one to several layers of coating material on the resist underlayer film, A resist can be applied. As a result, the pattern width of the resist becomes narrow, and even when the resist is thinly coated to prevent pattern collapse, the substrate can be processed by selecting an appropriate etching gas.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition and forming a hard mask by a coating material containing a silicon component or the like or a hard mask (for example, silicon nitride oxide) on the semiconductor substrate.
- a semiconductor device can be manufactured through a step of etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas and a step of processing a semiconductor substrate with a halogen-based gas with the patterned resist underlayer film.
- the resist underlayer film forming composition for lithography in the present invention has a light absorption site incorporated in the skeleton, so there is no diffused material in the photoresist during heating and drying. Moreover, since the light absorption site has a sufficiently large light absorption performance, the effect of preventing reflected light is high.
- the thermal stability is high, contamination of the upper layer film by decomposition products during baking can be prevented, and a temperature margin in the baking process can be provided. is there.
- the resist underlayer film material for lithography has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist or is used for the material or photoresist used in the photoresist.
- the film can be used as a film having a function of preventing an adverse effect on a substrate of a substance generated during exposure.
- the reaction mixture was diluted with 180.8 g of N-methylpyrrolidone, and potassium carbonate was removed by filtration.
- the obtained filtrate was neutralized by adding 1N HCl, and then stirred for a while.
- the obtained precipitate was suction filtered, and the filtrate was dried under reduced pressure at 60 ° C. overnight. And 54.8g of resin 1 was obtained.
- the obtained polymer corresponded to the formula (2-1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 2,900.
- the obtained polymer corresponded to the formula (2-2).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 2,900.
- the obtained polymer corresponded to Formula (2-3).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 3,400.
- the obtained precipitate was suction filtered, and the filtrate was dried under reduced pressure at 60 ° C. overnight. And 3.37g of resin 2 was obtained.
- the obtained polymer corresponded to the formula (1-4-1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 3,700.
- the obtained precipitate was suction filtered, and the filtrate was dried under reduced pressure at 60 ° C. overnight. And 4.85g of resin 3 was obtained.
- the obtained polymer corresponded to the formula (1-4-2).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 3,900.
- the solution was diluted with 40.0 g of N-methylpyrrolidone and dropped into a methanol solution to cause reprecipitation.
- the obtained precipitate was suction filtered, and the filtrate was dried under reduced pressure at 60 ° C. overnight. And 15.02g of resin 5 was obtained.
- the obtained polymer corresponded to the formula (1-4-11).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 7,400.
- the reaction mixture was diluted with 37.6 g of N-methylpyrrolidone and dropped into a methanol solution to cause reprecipitation.
- the obtained precipitate was suction filtered, and the filtrate was dried under reduced pressure at 60 ° C. overnight. And 13.12g of resin 6 was obtained.
- the obtained polymer corresponded to the formula (1-4-12).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC was 5,200.
- Epoxy group-containing benzene condensed cyclic compound (trade name: EPICLON HP-4700, epoxy value: 165 g / eq., Manufactured by DIC Corporation) 10.00 g, acrylic acid 4.37 g, ethyltriphenylphosphonium bromide 0.56 g, 34.91 g of propylene glycol monomethyl ether was added to 0.03 g of hydroquinone, and the mixture was heated and stirred at 100 ° C. for 21 hours in a nitrogen atmosphere.
- EPICLON HP-4700 epoxy value: 165 g / eq., Manufactured by DIC Corporation
- Cation exchange resin product name: Dowex [registered trademark] 550A, Muromachi Technos Co., Ltd. 15 g
- anion exchange resin trade name: Amberlite [registered trademark] 15 JWET, Organo Co., Ltd. 15 g
- ion exchange treatment was performed at room temperature for 4 hours.
- a compound solution was obtained.
- the obtained compound corresponded to Formula (2-2), and the weight average molecular weight Mw measured by GPC in polystyrene conversion was 1,400.
- Example 1 The resin obtained in Synthesis Example 1 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content 20.60% by mass). To 2.50 g of this resin solution, 0.05 g of propylene glycol monomethyl ether acetate containing 1. 1% by weight surfactant (manufactured by DIC Corporation, trade name Megafac R-40) and 2.60 g of propylene glycol monomethyl ether acetate were added. The solution was filtered through a polytetrafluoroethylene microfilter having a diameter of 0.1 ⁇ m to prepare a resist underlayer film forming composition solution.
- surfactant manufactured by DIC Corporation, trade name Megafac R-40
- Example 2 The resin obtained in Synthesis Example 2 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content: 18.67% by mass). To 2.80 g of this resin solution was added 0.05 g of propylene glycol monomethyl ether acetate containing 1. 1% by weight surfactant (manufactured by DIC Corporation, trade name Megafac R-40) and 2.38 g of propylene glycol monomethyl ether acetate. The solution was filtered through a polytetrafluoroethylene microfilter having a diameter of 0.1 ⁇ m to prepare a resist underlayer film forming composition solution.
- surfactant manufactured by DIC Corporation, trade name Megafac R-40
- Example 3 The resin obtained in Synthesis Example 3 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content: 20.00% by mass). To this resin solution 2.00 g, 1% by weight surfactant (manufactured by DIC Corporation, trade name Megafac R-40) -containing propylene glycol monomethyl ether acetate 0.04 g, propylene glycol monomethyl ether acetate 1.97 g, The solution was filtered through a polytetrafluoroethylene microfilter having a diameter of 0.1 ⁇ m to prepare a resist underlayer film forming composition solution.
- surfactant manufactured by DIC Corporation, trade name Megafac R-40
- Example 4 The resin obtained in Synthesis Example 4 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content: 13.65% by mass). To 5.85 g of this resin solution, 0.16 g of propylene glycol monomethyl ether acetate containing 1. 1% by weight surfactant (manufactured by DIC Corporation, trade name Megafac R-40) and 3.99 g of propylene glycol monomethyl ether acetate were added. The solution was filtered through a 0.1 ⁇ m polytetrafluoroethylene microfilter to prepare a resist underlayer film forming composition solution.
- surfactant manufactured by DIC Corporation, trade name Megafac R-40
- Example 5 The resin obtained in Synthesis Example 5 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content: 18.53% by mass). To 4.31 g of this resin solution, 0.16 g of propylene glycol monomethyl ether acetate containing 0.1% by mass surfactant (manufactured by DIC Corporation, trade name Megafac R-40) and 5.53 g of propylene glycol monomethyl ether acetate were added. The solution was filtered through a 0.1 ⁇ m polytetrafluoroethylene microfilter to prepare a resist underlayer film forming composition solution.
- Comparative Example 1 The resin obtained in Comparative Synthesis Example 1 was dissolved in propylene glycol monomethyl ether acetate and then subjected to ion exchange to obtain a resin solution (solid content: 16.94% by mass). To 3.00 g of this resin solution, 0.06 g of propylene glycol monomethyl ether acetate containing 1% by weight surfactant (manufactured by DIC Corporation, trade name Megafac R-40) and 2.04 g of propylene glycol monomethyl ether acetate were added, The solution was filtered through a polytetrafluoroethylene microfilter having a diameter of 0.1 ⁇ m to prepare a resist underlayer film forming composition solution.
- surfactant manufactured by DIC Corporation, trade name Megafac R-40
- Comparative Example 2 4.19 g of the resin solution (solid content is 25.02% by mass) obtained in Comparative Synthesis Example 2, 0.001 g of a surfactant (manufactured by DIC Corporation, trade name Megafac R-40), propylene glycol monomethyl ether 6 .62 g and 4.19 g of propylene glycol monomethyl ether acetate were added to prepare a resist underlayer film forming composition solution.
- a surfactant manufactured by DIC Corporation, trade name Megafac R-40
- the resist underlayer film forming compositions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were each applied (spin coated) onto a silicon wafer using a spinner.
- the film was heated on a hot plate at 215 ° C. for 1 minute to form a film (resist underlayer film) having a thickness of about 200 nm.
- the resist underlayer coating film is irradiated with UV light of 500 mJ / cm 2 by an UV irradiation device using a UV irradiation unit (wavelength 172 nm) manufactured by Ushio Electric Co., Ltd., and the solvent is removed by light irradiation (ultraviolet irradiation). The sex was confirmed.
- the solvent peelability was measured by immersing a 7: 3 mixed solvent of propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate for 1 minute in the coating film after ultraviolet irradiation, baking at 100 ° C. for 1 minute after spin drying, and measuring the film thickness. . Moreover, the film shrinkage ratio before and after irradiation with light was also calculated (results in Table 1).
- resist underlayer film forming composition solutions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were each applied onto a silicon wafer using a spin coater. Baking was performed on a hot plate at 215 ° C. for 1 minute to form a resist underlayer film (film thickness 0.05 ⁇ m). These resist underlayer films were measured for refractive index (n value) and optical absorption coefficient (also referred to as k value and attenuation coefficient) at wavelengths of 193 nm and 248 nm using a spectroscopic ellipsometer (results in Table 2).
- this resist underlayer coating film was irradiated with ultraviolet rays of 500 mJ / cm 2 by an ultraviolet irradiation device using a UV irradiation unit (wavelength 172 nm) manufactured by Ushio Electric Co., Ltd., and the wavelength after light irradiation (ultraviolet irradiation)
- the refractive index and optical extinction coefficient at 193 nm and 248 nm were measured (results in Table 3).
- the resist underlayer coating film was irradiated with ultraviolet rays of 500 mJ / cm 2 by an ultraviolet irradiation device using a UV irradiation unit (wavelength 172 nm) manufactured by Ushio Electric Co., Ltd., and Examples 1 to 3 and Comparative Example A comparison was made between 1 and 2 and the dry etching rate of the resist underlayer film.
- the results are shown in Table 4.
- the dry etching rate ratio is the dry etching rate ratio of (resist underlayer film) / (KrF photoresist) (result of Table 4).
- the step coverage of this substrate was observed using a scanning electron microscope (S-4800) manufactured by Hitachi High-Technologies Corporation, and the film thickness between the dense area (patterned portion) and the open area (unpatterned portion) of the stepped substrate.
- the flatness was evaluated by measuring the difference (application step between dense area and open area, called bias).
- bias application step between dense area and open area
- the flattening property means that a coated portion existing on the upper part of a portion where the pattern exists (dense area (pattern portion)) and a portion where the pattern does not exist (open area (non-pattern portion)). This means that the film thickness difference (Iso-dense bias) of the object is small (result of Table 6).
- the photocurable stepped substrate coating composition of the present invention is a film having a flatness capable of forming a coating film by photocuring which has high pattern filling properties and does not cause degassing or thermal shrinkage, and is irradiated with light.
- a stepped substrate coating composition capable of later forming a highly heat-resistant coating on a substrate.
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Abstract
Description
ところが、露光波長の短波長化に伴って焦点深度が低下するために、基板上に形成された被膜の平坦化性を向上させることが必要になる。微細なデザインルールを持つ半導体装置を製造するためには、基板上の平坦化技術が重要になってきている。
平坦化膜、例えばレジストの下に形成されるレジスト下層膜を光硬化により形成する方法が開示されている。
但し、R1において、酸素原子、カルボニル基、イオウ原子、-C(O)-O-、-C(O)-NRa-及び-NRb-は、それら同士で結合しない。
ここで、多核フェノールが有するヒドロキシル基の数とは、m×qを意図する。
式(1)中でXはカルボニル基である場合を好ましく用いることができる。
また、式(1)中のn1は1又は2であり、n2とn3が0であるポリマーを用いることができる。
上記段差基板被覆組成物は必要に応じて界面活性剤等の添加剤を含むことができる。
本発明に用いられる上記ポリマーは、平均分子量が600乃至1000000、又は600乃至200000、又は1500乃至15000である。
上記ポリマーは、分子間又は分子内で炭素と炭素の不飽和結合の光反応で架橋構造を形成することができるが、この炭素原子間の不飽和結合、即ち炭素原子間の不飽和二重結合を分子内に少なくとも1個有することができ、また分子内に複数個(例えば1乃至1000個)有することもできる。
式(3)中、A4及びA5はそれぞれヘテロ原子を含んでいてもよい炭素原子数6乃至48の芳香族環又はヘテロ原子を含んでいてもよい炭素原子数6乃至48の芳香族環を含む炭化水素基を示し、B4及びB5は上記式(2)と同一であり、n4は1≦n4≦4、n5は0≦n5≦4の整数であり、n4+n5=1乃至8の整数である。ヘテロ原子として、窒素原子、酸素原子があげられる。炭素原子数6乃至48の芳香族環は例えば、ベンゼン環、ビフェニル環、ターフェニレン環、フルオレン環、ナフタレン環、アントリル環、ピレン環、カルバゾール環、インドール環があげられる。
ポリマーが式(1)の単位構造と式(3)の単位構造を含む場合に、式(1)の単位構造:式(3)の単位構造はモル比で、1:0.1乃至1:10、又は1:0.5乃至1:5、又は1:1の割合で含有することができる。
上記基板はオープンエリア(非パターンエリア)と、DENCE(密)及びISO(粗)のパターンエリアを有し、パターンのアスペクト比が0.1乃至10を用いることができる。
本発明でリソグラフィー用レジスト下層膜材料を使用して形成したレジスト下層膜を有するレジストの現像液としては、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、ケイ酸ナトリウム、メタケイ酸ナトリウム、アンモニア水等の無機アルカリ類、エチルアミン、n-プロピルアミン等の第一アミン類、ジエチルアミン、ジーn-ブチルアミン等の第二アミン類、トリエチルアミン、メチルジエチルアミン等の第三アミン類、ジメチルエタノールアミン、トリエタノールアミン等のアルコールアミン類、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、コリン等の第4級アンモニウム塩、ピロール、ピペリジン等の環状アミン類、等のアルカリ類の水溶液を使用することができる。さらに、上記アルカリ類の水溶液にイソプロピルアルコール等のアルコール類、ノニオン系等の界面活性剤を適当量添加して使用することもできる。これらの中で好ましい現像液は第四級アンモニウム塩、さらに好ましくはテトラメチルアンモニウムヒドロキシド及びコリンである。
三口フラスコに1,1,1-トリス(4-ヒドロキシフェニル)エタン(東京化成工業株式会社製)50.0g、4,4-ジフルオロベンゾフェノン(東京化成工業株式会社製製)35.6g、炭酸カリウム(和光純薬工業株式会社製)31.37g、N-メチルピロリドン(関東化学株式会社製)272.9gを入れた。その後150℃まで加熱し、約2.5時間撹拌した。反応終了後、N-メチルピロリドン180.8gで希釈し、濾過により炭酸カリウムを取り除いた。得られたろ液に対して1N-HClを加えて中性とした後、しばらく撹拌した。この希釈溶液をメタノール/水=90/10(vol/vol)溶液中に滴下し、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂1を54.8g得た。得られたポリマーは式(2-1)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは2,900であった。
三口フラスコにTEP-DF(旭有機材株式会社製)30.0g、4,4-ジフルオロベンゾフェノン(東京化成工業株式会社製製)16.43g、炭酸カリウム(和光純薬工業株式会社製)14.47g、N-メチルピロリドン(関東化学株式会社製)142.1gを入れた。その後150℃まで加熱し、約4時間撹拌した。反応終了後、N-メチルピロリドン261.1gで希釈し、濾過により炭酸カリウムを取り除いた。得られたろ液に対して1N-HClを加えて中性とした後、しばらく撹拌した。この希釈溶液をメタノール/水=90/10(vol/vol)溶液中に滴下し、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂2を29.1g得た。得られたポリマーは式(2-2)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは2,900であった。
三口フラスコにTEP-TPA(旭有機材株式会社製)30.0g、4,4-ジフルオロベンゾフェノン(東京化成工業株式会社製製)13.81g、炭酸カリウム(和光純薬工業株式会社製)12.16g、N-メチルピロリドン(関東化学株式会社製)130.61gを入れた。その後150℃まで加熱し、約4時間撹拌した。反応終了後、N-メチルピロリドン252.3gで希釈し、濾過により炭酸カリウムを取り除いた。得られたろ液に対して1N-HClを加えて中性とした後、しばらく撹拌した。この希釈溶液をメタノール/水=90/10(vol/vol)溶液中に滴下し、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂3を18.6g得た。得られたポリマーは式(2-3)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは3,400であった。
ナスフラスコに樹脂1を5.00g、アリルグリシジルエーテル(東京化成工業株式会社製)3.54g、ヒドロキノン(東京化成工業株式会社製)0.02g、エチルトリフェニルホスホニウムブロマイド(北興化学工業株式会社製)0.58g、N-メチルピロリドン(関東化学株式会社製)9.17g、プロピレングリコールモノメチルエーテルアセテート 21.4gを入れた。その後100℃まで加熱し、約24時間撹拌した。
反応終了後、N-メチルピロリドン5.96gで希釈し、メタノール/水=90/10(vol/vol)溶液中に滴下することで、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして樹脂2を3.37g得た。得られたポリマーは式(1-4-1)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは3,700であった。
ナスフラスコに樹脂1を5.00g、メタクリル酸グリシジル(東京化成工業株式会社製)7.34g、ヒドロキノン(東京化成工業株式会社製)0.03g、エチルトリフェニルホスホニウムブロマイド(北興化学工業株式会社製)0.96g、N-メチルピロリドン(関東化学株式会社製)9.33g、プロピレングリコールモノメチルエーテルアセテート 21.8gを入れた。その後100℃まで加熱し、約18時間撹拌した。
反応終了後、N-メチルピロリドン22.2gで希釈し、メタノール/水=90/10(vol/vol)溶液中に滴下することで、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂3を4.85g得た。得られたポリマーは式(1-4-2)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは3,900であった。
ナスフラスコに樹脂1を5.00g、アリルブロミド(東京化成工業株式会社製)5.00g、炭酸カリウム(和光純薬工業株式会社製)3.97g、N-メチルピロリドン(関東化学株式会社製)20.59gを入れた。その後100℃まで加熱し、約24時間撹拌した。
反応終了後、N-メチルピロリドン15.1gで希釈し、濾過により炭酸カリウムを取り除いた。得られたろ液に対して1N-HClを加えて中性とした後、しばらく撹拌した。この希釈溶液をメタノール/水=90/10(vol/vol)溶液中に滴下し、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂4を4.00g得た。得られたポリマーは式(1-4-3)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは3,100であった。
ナスフラスコに樹脂2を10.00g、メタクリル酸グリシジル(東京化成工業株式会社製)12.68g、ヒドロキノン(東京化成工業株式会社製)0.05g、エチルトリフェニルホスホニウムブロマイド(北興化学工業株式会社製)1.16g、N-メチルピロリドン(関東化学株式会社製)17.07g、プロピレングリコールモノメチルエーテルアセテート 39.84gを入れた。その後100℃まで加熱し、約12時間撹拌した。
反応終了後、N-メチルピロリドン40.0gで希釈し、メタノール溶液中に滴下することで、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂5を15.02g得た。得られたポリマーは式(1-4-11)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは7,400であった。
ナスフラスコに樹脂3を10.00g、メタクリル酸グリシジル(東京化成工業株式会社製)11.24g、ヒドロキノン(東京化成工業株式会社製)0.04g、エチルトリフェニルホスホニウムブロマイド(北興化学工業株式会社製)1.47g、N-メチルピロリドン(関東化学株式会社製)15.93g、プロピレングリコールモノメチルエーテルアセテート 37.16gを入れた。その後100℃まで加熱し、約12時間撹拌した。
反応終了後、N-メチルピロリドン37.6gで希釈し、メタノール溶液中に滴下することで、再沈殿させた。得られた沈殿物を吸引ろ過後、ろ物を60℃で一晩減圧乾燥した。そして、樹脂6を13.12g得た。得られたポリマーは式(1-4-12)に相当した。GPCによりポリスチレン換算で測定される重量平均分子量Mwは5,200であった。
上記樹脂1を比較合成例1の樹脂として準備した。
エポキシ基含有ベンゼン縮合環式化合物(商品名:EPICLON HP-4700、エポキシ価:165g/eq.、DIC(株)製)10.00g、アクリル酸4.37g、エチルトリフェニルホスホニウムブロマイド0.56g、ヒドロキノン0.03gにプロピレングリコールモノメチルエーテル34.91gを加え、窒素雰囲気下、100℃で21時間加熱撹拌した。得られた溶液に陽イオン交換樹脂(製品名:ダウエックス〔登録商標〕550A、ムロマチテクノス(株))15g、陰イオン交換樹脂(商品名:アンバーライト〔登録商標〕15JWET、オルガノ(株))15gを加えて、室温で4時間イオン交換処理した。イオン交換樹脂を分離後、化合物溶液が得られた。得られた化合物は式(2-2)に相当し、GPCによりポリスチレン換算で測定される重量平均分子量Mwは1,400であった。
合成例1で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は20.60質量%)を得た。この樹脂溶液2.50gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.05g、プロピレングリコールモノメチルエーテルアセテート2.60g、を加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
合成例2で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は18.67質量%)を得た。この樹脂溶液2.80gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.05g、プロピレングリコールモノメチルエーテルアセテート2.38g、を加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
合成例3で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は20.00質量%)を得た。この樹脂溶液2.00gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.04g、プロピレングリコールモノメチルエーテルアセテート1.97g、を加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
合成例4で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は13.65質量%)を得た。この樹脂溶液5.85gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.16g、プロピレングリコールモノメチルエーテルアセテート3.99gを加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
合成例5で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は18.53質量%)を得た。この樹脂溶液4.31gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.16g、プロピレングリコールモノメチルエーテルアセテート5.53gを加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
比較合成例1で得た樹脂をプロピレングリコールモノメチルエーテルアセテートに溶解後、イオン交換を経て樹脂溶液(固形分は16.94質量%)を得た。この樹脂溶液3.00gに1質量%界面活性剤(DIC(株)製、商品名メガファックR-40)含有プロピレングリコールモノメチルエーテルアセテート0.06g、プロピレングリコールモノメチルエーテルアセテート2.04g、を加え、口径0.1μmのポリテトラフルオロエチレン製マイクロフィルターにて濾過して、レジスト下層膜形成組成物の溶液を調製した。
比較合成例2で得た樹脂溶液(固形分は25.02質量%)4.19gに界面活性剤(DIC(株)製、商品名メガファックR-40)0.001g、プロピレングリコールモノメチルエーテル6.62g、プロピレングリコールモノメチルエーテルアセテート4.19gを加え、レジスト下層膜形成組成物の溶液を調製した。
実施例1乃至5及び比較例1乃至2で調製されたレジスト下層膜形成組成物を、それぞれスピナーを用いてシリコンウェハー上に塗布(スピンコート)した。ホットプレート上で215℃、1分間加熱し、膜厚約200nmの被膜(レジスト下層膜)を形成した。このレジスト下層膜被覆膜をウシオ電機(株)製、UV照射ユニット(波長172nm)を用いた紫外線照射装置により、500mJ/cm2の紫外線照射を行い、光照射(紫外線照射)での溶剤剥離性を確認した。溶剤剥離性は紫外線照射後の塗布膜にプロピレングリコールモノメチルエーテルとプロピレングリコールモノメチルエーテルアセテートの7対3の混合溶剤を1分間浸漬し、スピンドライ後に100℃で1分間ベークし、膜厚を測定した。また、光照照射前後の膜収縮率も算出した(表1の結果)。
実施例1乃至5及び比較例1乃至2で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で215℃1分間焼成し、レジスト下層膜(膜厚0.05μm)を形成した。これらのレジスト下層膜を、分光エリプソメーターを用いて波長193nm及び248nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した(表2の結果)。また、このレジスト下層膜被覆膜をウシオ電機(株)製、UV照射ユニット(波長172nm)を用いた紫外線照射装置により、500mJ/cm2の紫外線照射を行い、光照射(紫外線照射)後の波長193nm及び248nmでの屈折率及び光学吸光係数を測定した(表3の結果)。
ドライエッチング速度の測定に用いたエッチャー及びエッチングガスは以下のものを用いた。
RIE-10NR(サムコ製):CF4
実施例1乃至5及び比較例1乃至2で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で215℃1分間焼成してレジスト下層膜(膜厚0.20μm)を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定し、実施例1乃至3及び比較例1乃至2とレジスト下層膜のドライエッチング速度との比較を行った。また、このレジスト下層膜被覆膜をウシオ電機(株)製、UV照射ユニット(波長172nm)を用いた紫外線照射装置により、500mJ/cm2の紫外線照射を行い、実施例1乃至3及び比較例1乃至2とレジスト下層膜のドライエッチング速度との比較を行った。結果を表4に示した。ドライエッチング速度比は(レジスト下層膜)/(KrFフォトレジスト)のドライエッチング速度比である(表4の結果)。
実施例1乃至5及び比較例1乃至2で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で215℃60秒間焼成して、レジスト下層膜(膜厚0.20μm)を形成した。また、このレジスト下層膜被覆膜をウシオ電機(株)製、UV照射ユニット(波長172nm)を用いた紫外線照射装置により、500mJ/cm2の紫外線照射を行った。得られた膜を室温(約20℃)から一分間に10℃ずつの割合で昇温加熱して大気中で熱重量分析を行い、重量減少の経時変化を追跡した。結果を表5に示す。
段差被覆性の評価として、200nm膜厚のSiO2基板で、トレンチ幅50nm、ピッチ100nmのデンスパターンエリア(DENSE)とパターンが形成されていないオープンエリア(OPEN)の被覆膜厚の比較を行った。実施例1乃至3及び比較例1乃至2のレジスト下層膜形成組成物を上記基板上に塗布後、215℃で60秒間焼成してレジスト下層膜を形成した。レジスト下層膜形成組成物は、ベタ基板上での膜厚が150nmになるように調製した。この基板の段差被覆性を日立ハイテクノロジーズ(株)製走査型電子顕微鏡(S-4800)を用いて観察し、段差基板のデンスエリア(パターン部)とオープンエリア(パターンなし部)との膜厚差(デンスエリアとオープンエリアとの塗布段差でありバイアスと呼ぶ)を測定することで平坦化性を評価した。ここで、平坦化性とは、パターンが存在する部分(デンスエリア(パターン部))と、パターンが存在しない部分(オープンエリア(パターンなし部))とで、その上部に存在する塗布された被覆物の膜厚差(Iso-denseバイアス)が小さいことを意味する(表6の結果)。
Claims (16)
- 式(1):
- A1は、式(1-1)又は式(1-2):
- A1がトリ(ヒドロキシフェニル)メタンから誘導される基、テトラキス(ヒドロキシフェニル)エタンから誘導される基、又はテトラキス(ヒドロキシフェニル)-p-キシレンから誘導される基であり、A2及びA3がベンゼン環、又はナフタレン環から誘導される基である請求項1に記載の光硬化性段差基板被覆組成物。
- Xがカルボニル基である請求項1乃至請求項3のいずれか1項に記載の光硬化性段差基板被覆組成物。
- 式(1)の単位構造がn1は1又は2であり、n2及びn3が0となる単位構造を含むポリマーである請求項1に記載の光硬化性段差基板被覆組成物。
- ポリマーが式(1)の単位構造、又は式(1)と式(3)の単位構造に更に式(1)においてn1=0、n2=0、及びn3=0となる式(1’)の単位構造を含む請求項1乃至請求項6のいずれか1項に記載の光硬化性段差基板被覆組成物。
- 段差基板被覆組成物が、半導体装置製造のリソグラフィー工程に用いられるレジスト下層膜形成組成物である請求項1乃至請求項7のいずれか1項に記載の光硬化性段差基板被覆組成物。
- 段差を有する基板に請求項1乃至請求項8のいずれか1項に記載の光硬化性段差基板被覆組成物を塗布する工程(i)、及び露光する工程(ii)を含む被覆基板の製造方法。
- 工程(i)の光硬化性段差基板被覆組成物を塗布した後に70乃至400℃の温度で、10秒乃至5分間の加熱を行う(ia)工程を加える請求項9に記載の被覆基板の製造方法。
- 工程(ii)の露光波長が150nm乃至248nmである請求項9又は請求項10に記載の被覆基板の製造方法。
- 工程(ii)の露光量が10mJ/cm2乃至3000mJ/cm2である請求項9乃至請求項11のいずれか1項に記載の被覆基板の製造方法。
- 基板がオープンエリア(非パターンエリア)と、DENCE(密)及びISO(粗)のパターンエリアを有し、パターンのアスペクト比が0.1乃至10である請求項9乃至請求項12のいずれか1項に記載の被覆基板の製造方法。
- オープンエリアとパターンエリアとのBias(塗布段差)が1乃至50nmである請求項13に記載の被覆基板の製造方法。
- 段差を有する基板上に請求項1乃至請求項8のいずれか1項に記載の段差基板被覆組成物により下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、レジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 段差を有する基板に請求項1乃至請求項8のいずれか1項に記載の光硬化性段差基板被覆組成物により下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、レジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
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JPWO2018186310A1 (ja) | 2020-02-13 |
CN110462520B (zh) | 2023-03-03 |
TW201900726A (zh) | 2019-01-01 |
JP2023100639A (ja) | 2023-07-19 |
KR102455502B1 (ko) | 2022-10-17 |
TWI768024B (zh) | 2022-06-21 |
KR20190131543A (ko) | 2019-11-26 |
JP7303495B2 (ja) | 2023-07-05 |
US20200301278A1 (en) | 2020-09-24 |
CN110462520A (zh) | 2019-11-15 |
US10871712B2 (en) | 2020-12-22 |
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