WO2018070327A1 - 感放射線性樹脂組成物及びレジストパターン形成方法 - Google Patents
感放射線性樹脂組成物及びレジストパターン形成方法 Download PDFInfo
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- WO2018070327A1 WO2018070327A1 PCT/JP2017/036196 JP2017036196W WO2018070327A1 WO 2018070327 A1 WO2018070327 A1 WO 2018070327A1 JP 2017036196 W JP2017036196 W JP 2017036196W WO 2018070327 A1 WO2018070327 A1 WO 2018070327A1
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Classifications
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Definitions
- the present invention relates to a radiation-sensitive resin composition and a resist pattern forming method.
- Such a radiation sensitive resin composition generates an acid in an exposed portion by irradiation with exposure light such as far ultraviolet rays, extreme ultraviolet rays (EUV), electron beams such as ArF excimer laser, and the exposed portion is exposed by the catalytic action of this acid. And a difference in dissolution rate of the unexposed portion with respect to the developer, and a resist pattern is formed on the substrate.
- exposure light such as far ultraviolet rays, extreme ultraviolet rays (EUV), electron beams such as ArF excimer laser
- Such a radiation sensitive resin composition has not only excellent resolution and rectangularity of the cross-sectional shape of the resist pattern, but also LWR (Line Width Roughness) performance in line and space pattern formation and CDU (Critical Dimension) in hole pattern formation. In addition to being excellent in uniformity, it is also required that a high-accuracy pattern can be obtained at a high yield with an excellent exposure margin.
- the present invention has been made based on the circumstances as described above, and its purpose is to provide a radiation-sensitive resin composition with excellent LWR performance, CDU performance, resolution, rectangular cross-sectional shape, and exposure margin. And a resist pattern forming method.
- the invention made in order to solve the above-mentioned problems includes a first structural unit (hereinafter also referred to as “structural unit (I)”) and a second structural unit (hereinafter referred to as “structural unit (II)” in the same or different polymers. ) ”And a third structural unit (hereinafter also referred to as“ structural unit (III) ”), a first radiation-sensitive acid, and a polymer component (hereinafter also referred to as“ [A] polymer component ”).
- a radiation-sensitive acid generator component hereinafter referred to as “[B1] acid generator”
- a second radiation-sensitive acid generator hereinafter also referred to as “[B2] acid generator”.
- [B] acid generator component wherein the structural unit (I) is a group represented by the following formula (1) (hereinafter referred to as “group ( I) "), a structural unit containing a hydroxyl group in which the structural unit (II) is bonded to an aromatic ring,
- the structural unit (III) is a structural unit containing an acid dissociable group, and the [B1] acid generator has a carbon atom adjacent to the sulfo group, and the carbon atom has a fluorine atom or monovalent fluorinated carbonization.
- a sulfonic acid to which a hydrogen group is bonded is generated, and the [B2] acid generator has a carbon atom adjacent to the sulfo group and a carbon atom adjacent to the carbon atom, and any of these carbon atoms is a fluorine atom.
- a sulfonic acid to which a monovalent fluorinated hydrocarbon group is not bonded, or a carboxylic acid having a carbon atom adjacent to a carboxy group and having a fluorine atom or a monovalent fluorinated hydrocarbon group bonded to the carbon atom is generated. It is a radiation sensitive resin composition.
- L is an (n + 1) -valent organic group having 3 to 20 carbon atoms and containing an alicyclic structure having 3 to 20 ring members.
- R 1 to R 6 are each independently hydrogen.
- 7 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, n is an integer of 1 to 3.
- n is 2 or more, a plurality of R 1 may be the same or different.
- the plurality of R 2 may be the same or different, the plurality of R 3 may be the same or different, the plurality of R 4 may be the same or different, and the plurality of R 5 may be the same or different. at best, a plurality of R 6 may be the same or different, a plurality of R 7 is either the same or different Which may be. * Indicates a site that binds to a portion other than the group represented by the above formula (1) in the first structural unit.)
- Another invention made to solve the above problems is a process of coating the radiation-sensitive resin composition on one surface of the substrate, a process of exposing a resist film obtained by the coating process, And a step of developing the exposed resist film.
- a resist pattern that exhibits excellent exposure margin, low LWR and CDU, high resolution, and excellent cross-sectional rectangularity is formed. can do. Therefore, these can be suitably used for manufacturing semiconductor devices that are expected to be further miniaturized in the future.
- the radiation-sensitive resin composition contains a [A] polymer component and a [B] acid generator component.
- the radiation-sensitive resin composition has, as a preferred component, a polymer having a mass content of fluorine atoms larger than that of the [C] acid diffusion controller, [D] solvent, and [A] polymer component (hereinafter referred to as “[E ] May also contain other optional components as long as the effects of the present invention are not impaired.
- the radiation-sensitive resin composition contains an [A] polymer component and an [B] acid generator component, so that it has excellent LWR performance, CDU performance, resolution, cross-sectional rectangularity and exposure margin. Degree (hereinafter collectively referred to as “LWR performance etc.”).
- LWR performance etc. degree
- the reason why the radiation-sensitive resin composition has the above-described configuration provides the above-mentioned effect is not necessarily clear, but can be inferred as follows, for example. That is, in the radiation sensitive resin composition, in addition to the acid dissociable group, the polymer component [A] has a relatively bulky alicyclic structure and a group (I) containing a fluorine atom and a hydroxyl group.
- the diffusion length of the generated acid can be shortened more appropriately, and the [B] acid generator component contains both the [B1] generator and the [B2] acid generator.
- a relatively strong acid and a weak acid can be generated.
- each component will be described.
- the polymer component is a polymer component having the structural unit (I), the structural unit (II) and the structural unit (III) in the same or different polymers.
- [A] As an aspect of the polymer component, for example, (i) a polymer having structural unit (I), structural unit (II) and structural unit (III) in the same polymer, (ii) structural unit ( (Iii) a polymer having the structural unit (I), a polymer having the structural unit (I), a polymer having the structural unit (II), and a polymer having the structural unit (III). (Iv) a polymer having the structural unit (I) and the structural unit (III), and a polymer having the structural unit (II).
- the polymer component may contain one or more of the above polymers. Of these, (i), (ii) and (vi) are preferred.
- the polymer component is composed of the structural unit (IV) containing the lactone structure, the cyclic carbonate structure, the sultone structure, or a combination thereof in the same or different polymer having the structural units (I) to (III) and the alcoholic component. It may have a structural unit (V) containing a hydroxyl group, and may have other structural units other than the structural units (I) to (V).
- the polymer component may have one or more of each structural unit. Hereinafter, each structural unit will be described.
- the structural unit (I) is a structural unit containing a group represented by the following formula (1).
- L is an (n + 1) -valent organic group having 3 to 20 carbon atoms and containing an alicyclic structure having 3 to 20 ring members.
- R 1 to R 6 are each independently a hydrogen atom, a halogen atom or a monovalent organic group having 1 to 20 carbon atoms. However, at least one of R 1 to R 6 is a fluorine atom or an organic group containing at least one fluorine atom.
- R 7 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- n is an integer of 1 to 3.
- the plurality of R 1 may be the same or different
- the plurality of R 2 may be the same or different
- the plurality of R 3 may be the same or different
- the plurality of R 4 May be the same or different
- the plurality of R 5 may be the same or different
- the plurality of R 6 may be the same or different
- the plurality of R 7 may be the same or different.
- Examples of the alicyclic structure having 3 to 20 ring members contained in the (n + 1) -valent organic group having 3 to 20 carbon atoms represented by L include, for example, a cyclopropane structure, a cyclobutane structure, a cyclopentane structure, a cyclohexane structure, and a cycloheptane structure.
- Monocyclic saturated alicyclic structures such as cyclooctane structures; Polycyclic saturated alicyclic structures such as norbornane structure, adamantane structure, tricyclodecane structure and tetracyclododecane structure; Monocyclic unsaturated alicyclic structures such as cyclopropene structure, cyclobutene structure, cyclopentene structure, cyclohexene structure, cycloheptene structure, cyclooctene structure; Examples thereof include polycyclic unsaturated alicyclic structures such as a norbornene structure, a tricyclodecene structure, and a tetracyclododecene structure. Among these, a monocyclic saturated alicyclic structure and a polycyclic saturated alicyclic structure are preferable.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 1 to R 6 include a monovalent hydrocarbon group having 1 to 20 carbon atoms and a divalent hydrocarbon between carbon-carbon of the hydrocarbon group.
- Examples include a group ( ⁇ ) containing a heteroatom-containing group, a group obtained by substituting a part or all of the hydrogen atoms of the hydrocarbon group and group ( ⁇ ) with a monovalent heteroatom-containing group.
- Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include a divalent chain hydrocarbon group having 1 to 20 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and 6 carbon atoms. And 20 divalent aromatic hydrocarbon groups.
- Examples of the monovalent chain hydrocarbon group having 1 to 20 carbon atoms include alkyl groups such as methyl, ethyl, propyl, and butyl groups; An alkenyl group of ethenyl group, propenyl group, butenyl group; Examples thereof include alkynyl groups such as ethynyl group, propynyl group and butynyl group.
- Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic alicyclic saturated hydrocarbon groups such as a cyclopentyl group and a cyclohexyl group; Monocyclic alicyclic unsaturated hydrocarbon groups such as cyclopentenyl group and cyclohexenyl group; Polycyclic alicyclic saturated hydrocarbon groups such as norbornyl group, adamantyl group and tricyclodecyl group; Examples thereof include polycyclic alicyclic unsaturated hydrocarbon groups such as norbornenyl group and tricyclodecenyl.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include aryl groups such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group; Examples thereof include aralkyl groups such as benzyl group, phenethyl group, and naphthylmethyl group.
- hetero atom constituting the monovalent and divalent heteroatom-containing group examples include an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, and a halogen atom.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- divalent heteroatom-containing group examples include —O—, —CO—, —S—, —CS—, —NR′—, a group in which two or more of these are combined, and the like.
- R ' is a hydrogen atom or a monovalent hydrocarbon group. Of these, —O— is preferable.
- Examples of the monovalent heteroatom-containing group include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom, hydroxy group, carboxy group, cyano group, amino group and sulfanyl group. Among these, a halogen atom is preferable, and a fluorine atom is more preferable.
- R 1 to R 6 are preferably a fluorine atom and a fluorinated alkyl group, more preferably a fluorine atom and a perfluoroalkyl group, and still more preferably a fluorine atom.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 7 include the same groups as those exemplified as the organic group for R 1 to R 6 above.
- R 7 is preferably a hydrogen atom.
- N is preferably 1 or 2, and more preferably 1.
- group (I) examples include groups represented by the following formulas (1-1) to (1-12) (hereinafter also referred to as “groups (I-1) to (I-12)”). .
- * represents a site bonded to a moiety other than the group (I) in the structural unit (I).
- structural unit (I) examples include a structural unit represented by the following formula (i-1) (hereinafter also referred to as “structural unit (I-1)”), and a structure represented by the following formula (i-2).
- a unit hereinafter also referred to as “structural unit (I-2)”).
- X is the group (I).
- R 8 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- R 9 is a single bond, —O— or a divalent organic group having 1 to 20 carbon atoms.
- R 10 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- R 8 is preferably a hydrogen atom or a methyl group, more preferably a methyl group, from the viewpoint of copolymerization of the monomer that provides the structural unit (I-1).
- R 9 is preferably —O—.
- R 10 is preferably a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms, and 9 to 9 carbon atoms. Twenty aralkyl groups are more preferred.
- the content rate of structural unit (I) 1 mol% is preferable with respect to all the structural units which comprise a [A] polymer component, 5 mol% is more preferable, 8 mol% is further more preferable, 12 Mole% is particularly preferred and 15 mole% is even more particularly preferred.
- 80 mol% is preferable, 50 mol% is more preferable, 40 mol% is further more preferable, 30 mol% is especially preferable, 25 mol% is further especially preferable.
- the structural unit (II) is a structural unit containing a hydroxyl group bonded to an aromatic ring.
- the aromatic ring examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a tetracene ring, and a pentacene ring.
- a benzene ring and an aphthalene ring are preferable, and a benzene ring is more preferable.
- group (II) examples include groups represented by the following formulas.
- structural unit (II) examples include a structural unit represented by the following formula (ii-1) (hereinafter also referred to as “structural unit (II-1)”).
- R 11 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- E is a single bond, —O—, —CO—, —COO— or —CONH—.
- Y is the group (II).
- R 11 is preferably a hydrogen atom or a methyl group from the viewpoint of copolymerization of the monomer that gives the structural unit (II-1).
- E is preferably a single bond or —COO—.
- the content rate of structural unit (II) 10 mol% is preferable with respect to all the structural units which comprise a [A] polymer component, 20 mol% is more preferable, 30 mol% is further more preferable, 35 Mole% is particularly preferred.
- 80 mol% is preferable, 70 mol% is more preferable, 60 mol% is further more preferable, 55 mol% is especially preferable.
- the structural unit (III) is a structural unit containing an acid dissociable group.
- the “acid-dissociable group” refers to a group that replaces a hydrogen atom such as a carboxy group or a hydroxy group and dissociates by the action of an acid.
- the [A] polymer component has the structural unit (III), whereby sensitivity is further increased, and as a result, LWR performance and the like can be further improved.
- structural unit (III) examples include a structural unit represented by the following formula (iii-1) (hereinafter, also referred to as “structural unit (III-1)”), and a structure represented by the following formula (iii-2).
- a unit hereinafter also referred to as “structural unit (III-2)”).
- R 14 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- R 15 is a monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 16 and R 17 are each independently a monovalent hydrocarbon group having 1 to 20 carbon atoms, or 3 to 20 carbon atoms composed of these groups together with the carbon atom to which they are bonded. Represents an alicyclic structure.
- R 18 represents a hydrogen atom or a methyl group.
- L 1 is a single bond, —CCOO— or —CONH—.
- R 19 , R 20 and R 21 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent oxyhydrocarbon group having 1 to 20 carbon atoms.
- R 14 is preferably a hydrogen atom or a methyl group, and more preferably a methyl group, from the viewpoint of the copolymerizability of the monomer that provides the structural unit (III-1).
- R 18 is preferably a hydrogen atom from the viewpoint of the copolymerizability of the monomer giving the structural unit (III-2).
- Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 15 to R 17 and R 19 to R 21 include, for example, a monovalent chain hydrocarbon group having 1 to 20 carbon atoms, 20 monovalent alicyclic hydrocarbon groups, monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms, and the like.
- Examples of the monovalent chain hydrocarbon group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t -Alkyl groups such as butyl and pentyl; Alkenyl groups such as ethenyl group, propenyl group, butenyl group, pentenyl group; Examples include alkynyl groups such as ethynyl group, propynyl group, butynyl group, and pentynyl group.
- Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic alicyclic saturated hydrocarbon groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; A polycyclic alicyclic saturated hydrocarbon group such as a norbornyl group, an adamantyl group, a tricyclodecyl group, a tetracyclododecyl group; Monocyclic alicyclic unsaturated hydrocarbon groups such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group; Examples thereof include polycyclic alicyclic saturated hydrocarbon groups such as norbornenyl group and tricyclodecenyl group.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include aryl groups such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group; Examples include aralkyl groups such as benzyl group, phenethyl group, naphthylmethyl group, and anthrylmethyl group.
- Examples of the alicyclic structure having 3 to 20 carbon atoms constituted by R 16 and R 17 together with the carbon atom to which they are bonded include a cyclopropane structure, a cyclobutane structure, a cyclopentane structure, a cyclohexane structure, a cycloheptane structure, Monocyclic alicyclic structures such as cyclooctane structures; Examples thereof include polycyclic alicyclic structures such as a norbornane structure, an adamantane structure, a tricyclodecane structure, and a tetracyclododecane structure.
- Examples of the monovalent oxyhydrocarbon group having 1 to 20 carbon atoms represented by R 19 , R 20 and R 21 include monovalent valences of 1 to 20 carbon atoms of the above R 15 to R 17 and R 19 to R 21.
- Examples of the hydrocarbon group include those containing an oxygen atom at the terminal on the bond side.
- R 19 , R 20 and R 21 are preferably a chain hydrocarbon group and a cycloalkyloxy group.
- structural unit (III-1) structural units represented by the following formulas (iii-1-1) to (iii-1-7) (hereinafter referred to as “structural units (III-1-1) to (III-1) ⁇ 5) ”) is preferred.
- the structural unit (III-2) is preferably a structural unit represented by the following formula (iii-2-1) (hereinafter also referred to as “structural unit (III-2-1)”).
- R 14 to R 17 have the same meanings as the above formula (iii-1).
- i, j and k are each independently an integer of 1 to 4.
- a part or all of the hydrogen atoms on the cycloalkane ring in the above formula (iii-1-3) may be substituted with an alkyl group having 1 to 10 carbon atoms.
- R 18 to R 21 have the same meaning as in the above formula (iii-2).
- structural units (III-1) structural units (III-1-1) to (III-1-3) and (III-1-5) to (III-1-7) are preferable.
- structural unit (III-2) the structural unit (III-2-1) is preferable.
- Examples of the structural unit (III-1) include a structural unit represented by the following formula.
- R 14 has the same meaning as in the above formula (iii-1).
- the structural unit (III-1) includes a structural unit derived from t-alkyl (meth) acrylate, a structural unit derived from 2-alkyl-2-adamantyl (meth) acrylate, and 1-alkyl-1-cyclopentyl (meth).
- Structural units derived from acrylate structural units derived from 2- (4-methylcyclohexane-1-yl) propan-1-yl (meth) acrylate, 2-alkyl-2-tetracyclododecan-yl (meth) acrylate
- Examples of the structural unit (III-2) include a structural unit represented by the following formula.
- R 18 has the same meaning as in the above formula (iii-2).
- the structural unit (III-2) is preferably a structural unit derived from p- (1-ethoxyethoxy) styrene.
- the content rate of structural unit (III) As a minimum of the content rate of structural unit (III), 20 mol% is preferred, 30 mol% is more preferred, 35 mol% is still more preferred, and 40 mol% is especially preferred. As an upper limit of the said content rate, 80 mol% is preferable, 70 mol% is more preferable, 65 mol% is further more preferable, 60 mol% is especially preferable. By making the content rate of structural unit (III) into the said range, the said radiation sensitive resin composition can improve LWR performance etc. more.
- the structural unit (IV) is a structural unit including a lactone structure, a cyclic carbonate structure, a sultone structure, or a combination thereof.
- the polymer component can further adjust the solubility in the developer, and as a result, the LWR performance and the like of the radiation sensitive resin composition can be further improved. Can be made. Moreover, the adhesiveness of the resist pattern formed from the said radiation sensitive resin composition and a board
- Examples of the structural unit (IV) include a structural unit represented by the following formula.
- R L1 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- the structural unit (IV) is preferably a structural unit containing a lactone structure, more preferably a structural unit containing a norbornane lactone structure or a structural unit containing a ⁇ -butyrolactone structure.
- the lower limit of the content ratio of the structural unit (IV) is preferably 1 mol% with respect to all the structural units constituting the [A] polymer component. 3 mol% is more preferable and 5 mol% is further more preferable.
- As an upper limit of the said content rate 70 mol% is preferable, 30 mol% is more preferable, and 15 mol% is further more preferable.
- the structural unit (V) is a structural unit containing an alcoholic hydroxyl group.
- the polymer component can further adjust the solubility in the developer, and as a result, the LWR performance and the like of the radiation sensitive resin composition can be further improved. Can be made. Moreover, the adhesiveness of the resist pattern formed from the said radiation sensitive resin composition and a board
- Examples of the structural unit (V) include a structural unit represented by the following formula.
- R L2 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
- the structural unit (V) is preferably a structural unit derived from 3-hydroxyadamantan-1-yl (meth) acrylate.
- the lower limit of the content ratio of the structural unit (V) is preferably 1 mol% with respect to all the structural units constituting the [A] polymer component. 3 mol is more preferable.
- As an upper limit of the said content rate 30 mol% is preferable and 10 mol% is more preferable.
- the polymer component may have other structural units other than the structural units (I) to (V) in the same or different polymers.
- other structural units include structural units containing a cyano group, a nitro group, or a sulfonamide group such as structural units derived from 2-cyanomethyladamantan-2-yl (meth) acrylate, and 2,2,2-trifluoroethyl Structural units containing fluorine atoms, such as structural units derived from (meth) acrylates, structural units derived from 1,1,1,3,3,3-hexafluoropropan-2-yl (meth) acrylates, derived from styrene
- a structural unit containing a non-acid-dissociable hydrocarbon group such as a structural unit derived from vinyl naphthalene, a structural unit derived from n-pentyl (meth) acrylate, or the like.
- the lower limit of the content ratio of the other structural units is preferably 1 mol%, and more preferably 3 mol%.
- As an upper limit of the said content rate 30 mol% is preferable and 10 mol% is more preferable.
- the lower limit of the content of the polymer component is preferably 50% by mass, more preferably 70% by mass, and still more preferably 80% by mass in terms of solid content. As a maximum of the above-mentioned content, 99 mass% is preferred, 98 mass% is more preferred, and 95 mass% is still more preferred.
- Solid content conversion means the ratio with respect to the total solid in a radiation sensitive resin composition, and the total solid in a radiation sensitive resin composition means the sum total of components other than [D] solvent.
- the polymer constituting the polymer component can be synthesized, for example, by polymerizing a monomer giving each structural unit in a suitable solvent using a radical polymerization initiator or the like.
- radical polymerization initiator examples include azobisisobutyronitrile (AIBN), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2-cyclopropylpropylene). Pionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), azo radical initiators such as dimethyl 2,2′-azobisisobutyrate; benzoyl peroxide, t-butyl hydroperoxide, And peroxide radical initiators such as cumene hydroperoxide. Of these, AIBN and dimethyl 2,2'-azobisisobutyrate are preferred, and AIBN is more preferred. These radical polymerization initiators can be used alone or in combination of two or more.
- Examples of the solvent used for the polymerization include alkanes such as n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Cycloalkanes such as cyclohexane, cycloheptane, cyclooctane, decalin, norbornane; Aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene; Halogenated hydrocarbons such as chlorobutanes, bromohexanes, dichloroethanes, hexamethylene dibromide, chlorobenzene; Saturated carboxylic acid esters such as ethyl acetate, n-butyl acetate, i-butyl acetate and methyl propionate; Ketones such as acetone, butanone, 4-methyl-2-p
- the lower limit of the reaction temperature in the polymerization is preferably 40 ° C, more preferably 50 ° C.
- 150 degreeC is preferable and 120 degreeC is more preferable.
- 1 hour is preferable and 2 hours is more preferable.
- the upper limit of the reaction time is preferably 48 hours, more preferably 24 hours.
- the lower limit of polystyrene-equivalent weight average molecular weight (Mw) by gel permeation chromatography (GPC) of the polymer component is preferably 1,000, more preferably 2,000, still more preferably 3,000, 5 Is particularly preferred.
- the upper limit of Mw is preferably 50,000, more preferably 30,000, still more preferably 20,000, and particularly preferably 10,000.
- the upper limit of the ratio (Mw / Mn) of Mw to the number average molecular weight (Mn) in terms of polystyrene by GPC of the polymer component is preferably 5, more preferably 3, still more preferably 2, and particularly 1.7 preferable.
- the lower limit of the ratio is usually 1 and is preferably 1.3.
- Mw and Mn of the polymer in this specification are values measured using GPC under the following conditions.
- GPC column 2 "G2000HXL” from Tosoh Corporation, 1 "G3000HXL” and 1 "G4000HXL” Column temperature: 40 ° C
- Elution solvent Tetrahydrofuran (Wako Pure Chemical Industries)
- Flow rate 1.0 mL / min
- Sample concentration 1.0% by mass
- Sample injection volume 100 ⁇ L
- Detector Differential refractometer Standard material: Monodisperse polystyrene
- the acid generator component includes [B1] acid generator and [B2] acid generator.
- the acid generator component may contain an acid generator other than [B1] acid generator and [B2] acid generator.
- the acid generator component is a substance that generates an acid upon exposure. Since the acid-dissociable group of the [A] polymer component or the like is dissociated by the generated acid to generate a carboxy group, a hydroxy group, or the like, and the solubility of the [A] polymer component or the like in the developer changes.
- a resist pattern can be formed from the radiation-sensitive resin composition.
- the acid generator is a sulfonic acid having a carbon atom adjacent to the sulfo group and having a fluorine atom or a monovalent fluorinated hydrocarbon group bonded to the carbon atom (hereinafter also referred to as “sulfonic acid (I)”). ).
- the sulfonic acid (I) is a sulfonic acid having a group represented by the following formula (A), for example.
- R G and R H are each independently a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms.
- Examples of the fluorinated hydrocarbon group having 1 to 20 carbon atoms represented by R G and R H include a part or all of hydrogen atoms of the hydrocarbon groups exemplified as the above R 1 to R 7 substituted with fluorine atoms And the like.
- R G and R H are preferably a fluorine atom and a perfluoroalkyl group, more preferably a fluorine atom and a trifluoromethyl group, and still more preferably a fluorine atom.
- Examples of the sulfonic acid (I) include a sulfonic acid represented by the following formula (3).
- R p1 is a monovalent group containing a ring structure having 6 or more ring members.
- R p2 is a divalent linking group.
- R p3 and R p4 are each independently a hydrogen atom, a fluorine atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms.
- R p5 and R p6 are each independently a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms.
- n p1 is an integer of 0 to 10.
- n p2 is an integer of 0 to 10.
- n p3 is an integer of 1 to 10.
- n p1 + n p2 + n p3 is 30 or less.
- the plurality of R p2 may be the same or different.
- the plurality of R p3 may be the same or different, and the plurality of R p4 may be the same or different.
- the plurality of R p5 may be the same or different, and the plurality of R p6 may be the same or different.
- Examples of the monovalent group including a ring structure having 6 or more ring members represented by R p1 include a monovalent group including an alicyclic structure having 6 or more ring members and an aliphatic heterocyclic structure having 6 or more ring members.
- Examples of the alicyclic structure having 6 or more ring members include monocyclic saturated alicyclic structures such as a cyclohexane structure, a cycloheptane structure, a cyclooctane structure, a cyclononane structure, a cyclodecane structure, and a cyclododecane structure; Monocyclic unsaturated alicyclic structures such as cyclohexene structure, cycloheptene structure, cyclooctene structure, cyclodecene structure; Polycyclic saturated alicyclic structures such as norbornane structure, adamantane structure, tricyclodecane structure and tetracyclododecane structure; Examples thereof include polycyclic unsaturated alicyclic structures such as a norbornene structure and a tricyclodecene structure.
- Examples of the aliphatic heterocyclic structure having 6 or more ring members include lactone structures such as a hexanolactone structure and a norbornane lactone structure; Sultone structures such as hexanosultone structure and norbornane sultone structure; An oxygen atom-containing heterocyclic structure such as an oxacycloheptane structure or an oxanorbornane structure; Nitrogen atom-containing heterocyclic structures such as azacyclohexane structure, diazabicyclooctane structure, azadecalin structure; Examples thereof include a sulfur atom-containing heterocyclic structure such as a thiacyclohexane structure and a thianorbornane structure.
- Examples of the aromatic ring structure having 6 or more ring members include a benzene structure, a naphthalene structure, a phenanthrene structure, and an anthracene structure.
- Examples of the aromatic heterocyclic structure having 6 or more ring members include oxygen atom-containing heterocyclic structures such as a pyran structure, a benzofuran structure, and a benzopyran structure; Examples thereof include a nitrogen atom-containing heterocyclic structure such as a pyridine structure, a pyrimidine structure and an indole structure.
- the lower limit of the number of ring members of the ring structure of R p1 is preferably 7, more preferably 8, more preferably 9, and particularly preferably 10.
- the upper limit of the number of ring members is preferably 15, more preferably 14, more preferably 13, and particularly preferably 12.
- a part or all of the hydrogen atoms contained in the ring structure of R p1 may be substituted with a substituent.
- substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom, hydroxy group, carboxy group, cyano group, nitro group, alkoxy group, alkoxycarbonyl group, alkoxycarbonyloxy group, acyl group, Examples include an acyloxy group. Of these, a hydroxy group is preferred.
- R p1 is preferably a monovalent group containing an alicyclic structure having 6 or more ring members and a monovalent group containing an aliphatic heterocyclic structure having 6 or more ring members, and 1 containing an alicyclic structure having 9 or more ring members. More preferred are monovalent groups and monovalent groups containing an aliphatic heterocyclic structure having 9 or more ring members, an adamantyl group, a hydroxyadamantyl group, a norbornane lactone-yl group, a norbornane sultone-yl group, and a 5-oxo-4-oxa group.
- a tricyclo [4.3.1.1 3,8 ] undecan-yl group is more preferred, and an adamantyl group is particularly preferred.
- Examples of the divalent linking group represented by R p2 include a carbonyl group, an ether group, a carbonyloxy group, a sulfide group, a thiocarbonyl group, a sulfonyl group, and a divalent hydrocarbon group.
- a carbonyloxy group, a sulfonyl group, an alkanediyl group and a divalent alicyclic saturated hydrocarbon group are preferable, a carbonyloxy group and a divalent alicyclic saturated hydrocarbon group are more preferable, and a carbonyloxy group And a norbornanediyl group are more preferable, and a carbonyloxy group is particularly preferable.
- Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R p3 and R p4 include an alkyl group having 1 to 20 carbon atoms.
- Examples of the monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms represented by R p3 and R p4 include a fluorinated alkyl group having 1 to 20 carbon atoms.
- R p3 and R p4 are preferably a hydrogen atom, a fluorine atom and a fluorinated alkyl group, more preferably a fluorine atom and a perfluoroalkyl group, and still more preferably a fluorine atom and a trifluoromethyl group.
- Examples of the monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms represented by R p5 and R p6 include a fluorinated alkyl group having 1 to 20 carbon atoms.
- R p5 and R p6 are preferably a fluorine atom and a fluorinated alkyl group, more preferably a fluorine atom and a perfluoroalkyl group, still more preferably a fluorine atom and a trifluoromethyl group, and particularly preferably a fluorine atom.
- n p1 is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 and 1.
- n p2 is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 and 1, and particularly preferably 0.
- np3 1 is preferable and 2 is more preferable.
- the upper limit of n p3 is preferably 4, more preferably 3, and even more preferably 2.
- the lower limit of n p1 + n p2 + n p3 is preferably 2 and more preferably 4.
- the upper limit of n p1 + n p2 + n p3 is preferably 20, and more preferably 10.
- Examples of the acid generator include an onium salt compound containing a sulfonate anion obtained by removing a proton from the sulfo group of sulfonic acid (I) and a monovalent radiation-sensitive onium cation (hereinafter referred to as “compound (4-1) ) ”), And — (C ⁇ N 2 ) — are bonded to two groups obtained by removing a hydrogen atom from the sulfo group of the sulfonic acid (I) (hereinafter also referred to as“ compound (4-2) ”) N-sulfonylimideoxy compound in which a group obtained by removing a hydrogen atom from the sulfo group of sulfonic acid (I) is bonded to the nitrogen atom of disulfonylimide group (hereinafter also referred to as “compound (4-3)”) Etc.
- Examples of the monovalent radiation-sensitive onium cation in the compound (4-1) include cations represented by the following formulas (Z-1) to (Z-3) (hereinafter referred to as “cations (Z-1) to (Z-1)”. -3) ”)) and the like.
- R a1 , R a2 and R a3 each independently represent an alkyl group having 1 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or —OSO 2 —R P or —SO 2 —R Q or a ring structure in which two or more of these groups are combined with each other.
- R P and R Q are each independently an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 5 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms.
- k1, k2 and k3 are each independently an integer of 0 to 5.
- R a4 is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an aromatic hydrocarbon group having 6 to 8 carbon atoms.
- k4 is an integer of 0 to 7. If R a4 is plural, the plurality of R a4 may be the same or different, and plural R a4 may represent a constructed ring aligned with each other.
- R a5 is an alkyl group having 1 to 7 carbon atoms or an aromatic hydrocarbon group having 6 or 7 carbon atoms. k5 is an integer of 0 to 6.
- R a5 is plural, the plurality of R a5 may be the same or different, and plural R a5 may represent a keyed configured ring structure.
- r is an integer of 0 to 3.
- R a6 is a single bond or a divalent organic group having 1 to 20 carbon atoms.
- t is an integer of 0-2.
- R a7 and R a8 each independently represent an alkyl group having 1 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, —OSO 2 —R R or — SO 2 —R S represents a ring structure in which two or more of these groups are combined with each other.
- R R and R S are each independently an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 5 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms.
- k6 and k7 are each independently an integer of 0 to 5.
- R a7, R a8, R when R and R S is plural respective plurality of R a7, R a8, R R and R S may be the same as or different from each other.
- Examples of the alkyl group represented by R a1 to R a3 , R a4 , R a5 , R a7 and R a8 include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group and an n-butyl group; Examples thereof include branched alkyl groups such as i-propyl group, i-butyl group, sec-butyl group and t-butyl group.
- Examples of the aromatic hydrocarbon group represented by R a1 to R a3 , R a4 and R a5 include aryl groups such as phenyl group, tolyl group, xylyl group, mesityl group and naphthyl group; Examples include aralkyl groups such as benzyl group and phenethyl group.
- Examples of the aromatic hydrocarbon group represented by R a4 and R a5 include a phenyl group, a tolyl group, and a benzyl group.
- Examples of the divalent organic group represented by R a6 include a group similar to L 1 in the above formula (1).
- the hydrogen atom of the alkyl group and aromatic hydrocarbon group includes, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, a hydroxy group, a carboxy group, a cyano group, a nitro group, an alkoxy group, an alkoxy group.
- a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, a hydroxy group, a carboxy group, a cyano group, a nitro group, an alkoxy group, an alkoxy group.
- a carbonyl group an alkoxycarbonyloxy group, an acyl group, an acyloxy group, or the like.
- a halogen atom is preferable, and a fluorine atom is more preferable.
- R a1 to R a3 , R a4 , R a5 , R a7 and R a8 include an unsubstituted alkyl group, a fluorinated alkyl group, an unsubstituted monovalent aromatic hydrocarbon group, —OSO 2 —R ′′ and —SO 2 —R ′′ is preferable, a fluorinated alkyl group and an unsubstituted monovalent aromatic hydrocarbon group are more preferable, and a fluorinated alkyl group is more preferable.
- R ′′ is an unsubstituted monovalent alicyclic hydrocarbon group or an unsubstituted monovalent aromatic hydrocarbon group.
- the hydrogen atom of the alicyclic hydrocarbon group represented by R P and R Q in the formula (Z-1) and R R and R S in the formula (Z-3) is the same as the above R a1 etc. It may be substituted with a substituent.
- k1, k2 and k3 are preferably integers of 0 to 2, more preferably 0 and 1, and even more preferably 0.
- K4 in the formula (Z-2) is preferably an integer of 0 to 2, more preferably 0 and 1, and still more preferably 1.
- k5 is preferably an integer of 0 to 2, more preferably 0 and 1, and still more preferably 0.
- r, 2 and 3 are preferable, and 2 is more preferable.
- t, 0 and 1 are preferable, and 0 is more preferable.
- k6 and k7 are preferably integers of 0 to 2, more preferably 0 and 1, and still more preferably 0.
- examples of the compound (4-1) include compounds represented by the following formulas (4-1-1) to (4-1-19) (hereinafter referred to as “compound (4-1-1)”. ) To (4-1-19) ”, etc., as the compound (4-2), for example, a compound represented by the following formula (4-2-1) (hereinafter referred to as“ compound (4-2-2- Examples of the compound (4-3) include a compound represented by (4-3-1) (hereinafter, also referred to as “compound (4-3-1)”) and the like. It is done.
- Z + is a monovalent radiation-sensitive onium cation.
- Examples of the acid generator compound (4-1) include compounds containing an anion represented by the following formula and a monovalent radiation-sensitive onium cation.
- the lower limit of the content of the [B1] acid generator relative to the entire acid generator component is preferably 10% by mass, more preferably 20% by mass, and even more preferably 30% by mass.
- 80 mass% is preferable, 70 mass% is more preferable, and 60 mass% is further more preferable.
- the acid generator has a carbon atom adjacent to the sulfo group and a carbon atom adjacent to the carbon atom, and a fluorine atom or a monovalent fluorinated hydrocarbon group is bonded to any of these carbon atoms.
- Sulfonic acid hereinafter also referred to as “sulfonic acid (II)”
- carboxylic acid having a carbon atom adjacent to the carboxy group and having a fluorine atom or a monovalent fluorinated hydrocarbon group bonded to the carbon atom
- the acid generator is also referred to as “carboxylic acid (II)”.
- Examples of the sulfonic acid (II) include a sulfonic acid represented by the following formula (2).
- R A , R B and R C are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, or two or more of these groups Represents an alicyclic structure having 3 to 20 ring members constituted by carbon atoms to which they are combined with each other.
- the bonding site with the carbon atom adjacent to the sulfo group in the organic group is a carbon atom, and no fluorine atom or fluorinated hydrocarbon group is bonded to the carbon atom.
- At least one of R A , R B and R C is the organic group.
- Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R A , R B and R C include, among the monovalent organic groups having 1 to 20 carbon atoms exemplified as the above R 1 to R 7 , Examples include a bonding site with a carbon atom adjacent to the sulfo group, which is a carbon atom, and a fluorine atom or a fluorinated hydrocarbon group is not bonded to this carbon atom. Among these, a monovalent hydrocarbon group having 1 to 20 carbon atoms is preferable, and an alkyl group and an alicyclic saturated hydrocarbon group are more preferable.
- Part or all of the hydrogen atoms of the hydrocarbon group, the alkyl group, and the alicyclic saturated hydrocarbon group are a morpholino group, an oxo group ( ⁇ O), a phenyloxy group, a phenyloxycarbonyl group, or a carbon number. It may be substituted with 1 to 8 alkoxy groups or the like.
- R A , R B and R C are preferably hydrogen atoms, more preferably two are hydrogen atoms.
- Examples of the alicyclic structure having 3 to 20 ring members constituted by two or more of R A , R B and R C include monocyclic alicyclic structures such as cyclohexane structures and polycyclic structures such as tetracyclododecane structures. Examples include alicyclic structures.
- carboxylic acid (II) examples include perfluoroalkane carboxylic acids such as nonafluoro n-butane carboxylic acid and tridecafluoro n-hexane carboxylic acid, perfluorocyclocarboxylic acids such as nonafluorocyclopentane carboxylic acid and undecafluorocyclohexane carboxylic acid.
- carboxylic acids in which a fluorine atom is bonded to a carbon atom adjacent to a carboxy group such as alkanecarboxylic acid.
- the acid generator includes an onium salt compound containing an anion obtained by removing a proton from the sulfo group of sulfonic acid (II) and a monovalent radiation-sensitive onium cation (hereinafter referred to as “compound (5-1)”). And an onium salt compound (hereinafter also referred to as “compound (5-2)”) containing an anion obtained by removing a proton from the carboxy group of carboxylic acid (II) and a monovalent radiation-sensitive onium cation. .
- Examples of the monovalent radiation-sensitive onium cation include cations similar to those exemplified as the monovalent radiation-sensitive onium cation possessed by the compound (4-1).
- examples of the compound (5-1) include compounds represented by the following formulas (5-1-1) to (5-1-5) as the compound (5-2): Examples thereof include compounds represented by (5-2-1) and (5-2-2) (hereinafter also referred to as “compounds (5-2-1) and (5-2-2)”) and the like. It is done.
- Z + is a monovalent radiation-sensitive onium cation.
- the acid generator compound (5-2) includes, for example, a compound containing an anion represented by the following formulas (A-1) to (A-53) and a monovalent radiation-sensitive onium cation. And so on.
- the lower limit of the content of the [B2] acid generator relative to the entire acid generator component is preferably 20% by mass, more preferably 30% by mass, and even more preferably 40% by mass.
- As an upper limit of the said content 90 mass% is preferable, 80 mass% is more preferable, and 70 mass% is further more preferable.
- the content of the acid generator within the above range, the LWR performance and the like of the radiation-sensitive resin composition can be further improved.
- One or two or more acid generators can be used.
- Examples of other acid generators include [B1] acid generators and onium salt compounds other than [B2] acid generators, N-sulfonylimidooxy compounds, sulfonimide compounds, halogen-containing compounds, diazoketone compounds, and the like. Specific examples of the other acid generators include compounds described in paragraphs [0080] to [0113] of JP2009-134088A. 1 type (s) or 2 or more types can be used for another acid generator.
- the lower limit of the total content of the [B1] acid generator and the [B2] acid generator with respect to the entire acid generator component is preferably 70% by mass, more preferably 80% by mass, and even more preferably 90% by mass. .
- the upper limit of the total content is, for example, 100% by mass.
- the lower limit of the content of the acid generator component is preferably 1 part by mass, more preferably 5 parts by mass, and even more preferably 10 parts by mass with respect to 100 parts by mass of the polymer component [A]. Part is particularly preferred. As an upper limit of the said content, 50 mass parts is preferable, 40 mass parts is more preferable, 30 mass parts is further more preferable, 25 mass parts is especially preferable. [B] By making content of an acid generator component into the said range, the LWR performance of the said radiation sensitive resin composition etc. can be improved more.
- the radiation-sensitive resin composition may contain a [C] acid diffusion controller (except for those corresponding to the [B] acid generator component), if necessary.
- Examples of the acid diffusion control agent include nitrogen-containing compounds and photodegradable bases that are exposed to light and generate weak acids.
- the acid diffusion controller controls the diffusion phenomenon in the resist film of the acid generated from the [B] acid generator component by exposure, and has an effect of suppressing an undesirable chemical reaction in the non-exposed region. Further, the storage stability of the radiation sensitive resin composition is improved, and the resolution as a resist is further improved. Furthermore, a change in the line width of the resist pattern due to fluctuations in the holding time from exposure to development processing can be suppressed, and a radiation-sensitive resin composition excellent in process stability can be obtained.
- nitrogen-containing compound examples include a compound represented by the following formula (6) (hereinafter also referred to as “nitrogen-containing compound (I)”), a compound having two nitrogen atoms (hereinafter “nitrogen-containing compound (II)”). And compounds having three nitrogen atoms (hereinafter also referred to as “nitrogen-containing compound (III)”), amide group-containing compounds, urea compounds, nitrogen-containing heterocyclic compounds, and the like.
- R 22A , R 22B and R 22C are each independently a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group, aryl group or aralkyl group. .
- nitrogen-containing compound (I) examples include monoalkylamines such as n-hexylamine; dialkylamines such as di-n-butylamine; trialkylamines such as triethylamine and tri-n-pentylamine; aniline, 2, And aromatic amines such as 6-di-propylaniline.
- nitrogen-containing compound (II) examples include ethylenediamine, N, N, N ′, N′-tetramethylethylenediamine, and the like.
- nitrogen-containing compound (III) examples include polyamine compounds such as polyethyleneimine and polyallylamine; and polymers such as dimethylaminoethylacrylamide.
- amide group-containing compound examples include formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, propionamide, benzamide, pyrrolidone, N-methylpyrrolidone and the like. It is done.
- urea compound examples include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea, tributylthiourea and the like.
- nitrogen-containing heterocyclic compound examples include pyridines such as pyridine and 2-methylpyridine; morpholines such as N-propylmorpholine and N- (undecan-1-ylcarbonyloxyethyl) morpholine; pyrazine, pyrazole and the like.
- a nitrogen-containing compound having an acid dissociable group can also be used.
- the nitrogen-containing compound having an acid dissociable group include Nt-butoxycarbonylpiperidine, Nt-butoxycarbonylimidazole, Nt-butoxycarbonylbenzimidazole, Nt-butoxycarbonyl-2-phenylbenzimidazole.
- N- (t-butoxycarbonyl) di-n-octylamine N- (t-butoxycarbonyl) diethanolamine
- N- (t-butoxycarbonyl) dicyclohexylamine N- (t-butoxycarbonyl) diphenylamine
- Nt -Butoxycarbonyl-4-hydroxypiperidine Nt-amyloxycarbonyl-4-hydroxypiperidine and the like.
- the nitrogen-containing compound is preferably a nitrogen-containing compound (I) or a nitrogen-containing heterocyclic compound, more preferably a trialkylamine, an aromatic amine or a morpholine, tri-n-pentylamine, 2,6-dii- More preferred are propylaniline and N- (undecan-1-ylcarbonyloxyethyl) morpholine.
- Examples of the photodegradable base include sulfonium salt compounds represented by the following formula (7-1), onium salt compounds such as iodonium salt compounds represented by the following formula (7-2), and the like.
- R 23 to R 27 are each independently a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, or a halogen atom.
- E ⁇ and Q ⁇ are each independently OH ⁇ , R ⁇ —COO ⁇ , R ⁇ —N ⁇ —SO 2 —R ⁇ or an anion represented by the following formula (7-3).
- R ⁇ is independently an alkyl group, a monovalent alicyclic saturated hydrocarbon group, an aryl group or an aralkyl group.
- R ⁇ is a fluorinated alkyl group.
- R 28 represents an alkyl group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.
- u is an integer of 0-2. When u is 2, two R 28 may be the same or different.
- Examples of the photodegradable base include compounds represented by the following formulas.
- the photodegradable base is preferably a sulfonium salt, more preferably a triarylsulfonium salt, and still more preferably triphenylsulfonium salicylate.
- the said radiation sensitive resin composition contains a [C] acid diffusion control agent
- a [C] acid diffusion control agent as a minimum of content of a [C] acid diffusion control agent, with respect to 100 mass parts of [A] polymer components, 0. 1 part by mass is preferable, 0.5 part by mass is more preferable, 1 part by mass is further preferable, and 3 parts by mass is particularly preferable.
- As an upper limit of the said content 20 mass parts is preferable, 15 mass parts is more preferable, 10 mass parts is further more preferable, and 8 mass parts is especially preferable.
- the radiation sensitive resin composition may contain one or more [C] acid diffusion control agents.
- the solvent is not particularly limited as long as it can dissolve or disperse at least the [A] polymer component, the [B] acid generator component, and the optionally contained [C] acid diffusion controller.
- Examples of the solvent include alcohol solvents, ether solvents, ketone solvents, amide solvents, ester solvents, hydrocarbon solvents, and the like.
- alcohol solvents examples include aliphatic monoalcohol solvents having 1 to 18 carbon atoms such as 4-methyl-2-pentanol and n-hexanol; An alicyclic monoalcohol solvent having 3 to 18 carbon atoms such as cyclohexanol; A polyhydric alcohol solvent having 2 to 18 carbon atoms such as 1,2-propylene glycol; Examples thereof include polyhydric alcohol partial ether solvents having 3 to 19 carbon atoms such as propylene glycol monomethyl ether.
- ether solvents include dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether, and diheptyl ether; Cyclic ether solvents such as tetrahydrofuran and tetrahydropyran; And aromatic ring-containing ether solvents such as diphenyl ether and anisole.
- dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether, and diheptyl ether
- Cyclic ether solvents such as tetrahydrofuran and tetrahydropyran
- aromatic ring-containing ether solvents such as diphenyl ether and anisole.
- ketone solvent examples include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl-iso-butyl ketone, 2-heptanone, ethyl-n-butyl ketone, methyl-n-hexyl ketone, Chain ketone solvents such as di-iso-butyl ketone and trimethylnonanone: Cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone: Examples include 2,4-pentanedione, acetonylacetone, acetophenone, and the like.
- amide solvent examples include cyclic amide solvents such as N, N′-dimethylimidazolidinone and N-methylpyrrolidone; Examples thereof include chain amide solvents such as N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, and N-methylpropionamide.
- cyclic amide solvents such as N, N′-dimethylimidazolidinone and N-methylpyrrolidone
- chain amide solvents such as N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, and N-methylpropionamide.
- ester solvents include monocarboxylic acid ester solvents such as n-butyl acetate and ethyl lactate; Polyhydric alcohol carboxylate solvents such as propylene glycol acetate; Polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate; Polycarboxylic acid diester solvents such as diethyl oxalate; Examples thereof include carbonate solvents such as dimethyl carbonate and diethyl carbonate.
- monocarboxylic acid ester solvents such as n-butyl acetate and ethyl lactate
- Polyhydric alcohol carboxylate solvents such as propylene glycol acetate
- Polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate
- Polycarboxylic acid diester solvents such as diethyl oxalate
- Examples thereof include carbonate solvents such as dimethyl carbonate and diethyl carbonate.
- hydrocarbon solvent examples include aliphatic hydrocarbon solvents having 5 to 12 carbon atoms such as n-pentane and n-hexane; Examples thereof include aromatic hydrocarbon solvents having 6 to 16 carbon atoms such as toluene and xylene.
- a solvent can contain 1 sort (s) or 2 or more sorts.
- the polymer is a polymer having a larger mass content of fluorine atoms than the [A] polymer component.
- the said radiation sensitive resin composition can contain a [E] polymer as a water-repellent additive, for example.
- the lower limit of the fluorine atom content of the polymer is preferably 1% by mass, more preferably 2% by mass, further preferably 4% by mass, and particularly preferably 7% by mass.
- the upper limit of the fluorine atom content is preferably 60% by mass, more preferably 40% by mass, and even more preferably 30% by mass.
- the fluorine atom content (% by mass) of the polymer can be calculated from the structure of the polymer obtained by measuring the 13 C-NMR spectrum or the like.
- Examples of the structural unit possessed by the [E] polymer include the following structural unit (Ea) and the following structural unit (Eb).
- the polymer may have one or more structural units (Ea) and structural units (Eb).
- the structural unit (Ea) is a structural unit represented by the following formula (8a).
- a polymer can adjust a fluorine atom content rate by having a structural unit (Ea).
- RD is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
- G is a single bond, an oxygen atom, a sulfur atom, —CO—O—, —SO 2 —O—NH—, —CO—NH— or —O—CO—NH—.
- R E is a monovalent fluorinated chain hydrocarbon group having 1 to 6 carbon atoms or a monovalent fluorinated alicyclic hydrocarbon group having 4 to 20 carbon atoms.
- the monovalent fluorinated chain hydrocarbon group having 1 to 6 carbon atoms represented by R E such as trifluoromethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 2,2 , 3,3,3-pentafluoropropyl group, 1,1,1,3,3,3-hexafluoropropyl group, perfluoro n-propyl group, perfluoro i-propyl group, perfluoro n-butyl group, Examples include perfluoro i-butyl group, perfluoro t-butyl group, 2,2,3,3,4,4,5,5-octafluoropentyl group, perfluorohexyl group and the like.
- the monovalent fluorine-cycloaliphatic hydrocarbon radical having 4 to 20 carbon atoms represented by R E for example mono-fluoro cyclopentyl group, difluorocyclopentyl groups, perfluorocyclopentyl group, monofluoromethyl cyclohexyl group, difluorocyclohexyl group, Examples include a perfluorocyclohexylmethyl group, a fluoronorbornyl group, a fluoroadamantyl group, a fluorobornyl group, a fluoroisobornyl group, a fluorotricyclodecyl group, and a fluorotetracyclodecyl group.
- Examples of the monomer that gives the structural unit (Ea) include linear partially fluorinated alkyl (meth) acrylates such as 2,2,2-trifluoroethyl (meth) acrylate; Branched partially fluorinated alkyl (meth) acrylates such as 1,1,1,3,3,3-hexafluoro i-propyl (meth) acrylate; Linear perfluoroalkyl (meth) acrylates such as perfluoroethyl (meth) acrylate; (Meth) acrylic acid ester having a fluorinated chain hydrocarbon group such as branched perfluoroalkyl (meth) acrylic acid ester such as perfluoro i-propyl (meth) acrylic acid ester; (Meth) acrylic having a monocyclic fluorinated alicyclic saturated hydrocarbon group such as perfluorocyclohexylmethyl (meth) acrylic acid ester, monofluorocyclopentyl (meth) acrylic acid este
- (meth) acrylic acid esters having a fluorinated chain hydrocarbon group are preferred, linear partially fluorinated alkyl (meth) acrylic acid esters are more preferred, and 2,2,2-trifluoroethyl (meth) Acrylic acid esters are more preferred.
- the lower limit of the content ratio of the structural unit (Ea) is preferably 5 mol% with respect to all structural units constituting the [E] polymer. More preferably, mol% is more preferable, and 20 mol% is still more preferable. As an upper limit of the said content rate, 95 mol% is preferable, 75 mol% is more preferable, and 50 mol% is further more preferable. By setting such a content ratio, a higher dynamic contact angle on the resist film surface can be expressed at the time of immersion exposure.
- the structural unit (Eb) is a structural unit represented by the following formula (8b). Since the [E] polymer has a structural unit (Eb) and becomes hydrophobic, the dynamic contact angle of the resist film surface formed from the radiation-sensitive resin composition can be further improved.
- R ⁇ F > is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
- R 29 is an (s + 1) -valent hydrocarbon group having 1 to 20 carbon atoms, and an oxygen atom, a sulfur atom, —NR′—, a carbonyl group, —CO—O—, or a terminal at the R 30 side of R 29 Also includes a structure in which —CO—NH— is bonded.
- R ′ is a hydrogen atom or a monovalent organic group.
- R 30 is a single bond, a divalent chain hydrocarbon group having 1 to 10 carbon atoms, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms.
- X 2 is a divalent fluorinated chain hydrocarbon group having 1 to 20 carbon atoms.
- a 1 is an oxygen atom, —NR ′′ —, —CO—O— *, or —SO 2 —O— *.
- R ′′ is a hydrogen atom or a monovalent organic group. * Indicates a binding site that binds to R 31.
- R 31 is a hydrogen atom or a monovalent organic group.
- s is an integer of 1 to 3. However, when s is 2 or 3, the plurality of R 30 , X 2 , A 1 and R 31 may be the same or different.
- R 31 is a hydrogen atom, it is preferable in that the solubility of the [E] polymer in an alkaline developer can be improved.
- Examples of the monovalent organic group represented by R 31 include an acid dissociable group, an alkali dissociable group, or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent.
- the polymer may have a structural unit containing an acid dissociable group (hereinafter, also referred to as “structural unit (Ec)”) in addition to the structural units (Ea) and (Eb) (however, Except those corresponding to the structural unit (Eb)).
- structural unit (Ec) an acid dissociable group
- the shape of the resulting resist pattern becomes better.
- the structural unit (Ec) include the structural unit (III) in the polymer component [A].
- the lower limit of the content ratio of the structural unit (Ec) is preferably 5 mol% with respect to all the structural units constituting the [E] polymer. Mole% is more preferable, and 50 mol% is more preferable. As an upper limit of the said content rate, 90 mol% is preferable, 80 mol% is more preferable, and 70 mol% is further more preferable.
- the radiation-sensitive resin composition may contain one or more [E] polymers.
- the radiation-sensitive resin composition may contain other optional components in addition to the components [A] to [E].
- other optional components include uneven distribution accelerators, surfactants, alicyclic skeleton-containing compounds, and sensitizers. Each of these other optional components may be used alone or in combination of two or more.
- the uneven distribution accelerator has an effect of segregating the [E] polymer on the resist film surface more efficiently when the radiation-sensitive resin composition contains the [E] polymer.
- the uneven distribution accelerator By adding the uneven distribution accelerator to the radiation sensitive resin composition, the amount of the [E] polymer added can be reduced as compared with the conventional case. Therefore, it is possible to further suppress the elution of components from the resist film to the immersion liquid without impairing the LWR performance, etc., and to perform immersion exposure at a higher speed by high-speed scanning, resulting in a watermark defect. It is possible to improve the hydrophobicity of the resist film surface that suppresses immersion-derived defects such as the above.
- Examples of such an uneven distribution promoter include low molecular compounds having a relative dielectric constant of 30 or more and 200 or less and a boiling point at 1 atm of 100 ° C. or more.
- Specific examples of such compounds include lactone compounds, carbonate compounds, nitrile compounds, and polyhydric alcohols.
- lactone compound examples include ⁇ -butyrolactone, valerolactone, mevalonic lactone, norbornane lactone, and the like.
- carbonate compound examples include propylene carbonate, ethylene carbonate, butylene carbonate, vinylene carbonate, and the like.
- nitrile compound examples include succinonitrile.
- polyhydric alcohol examples include glycerin.
- the said radiation sensitive resin composition contains uneven distribution accelerator
- 10 mass parts is preferable with respect to 100 mass parts of [A] polymer components, 15 masses Part is more preferable, 20 parts by mass is further preferable, and 25 parts by mass is particularly preferable.
- 500 mass parts is preferable, 300 mass parts is more preferable, 200 mass parts is further more preferable, 100 mass parts is especially preferable.
- Surfactants have the effect of improving coatability, striation, developability, and the like.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol diacrylate.
- Nonionic surfactants such as stearate; commercially available products include KP341 (Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75, no.
- the alicyclic skeleton-containing compound has an effect of improving dry etching resistance, pattern shape, adhesion to the substrate, and the like.
- Examples of the alicyclic skeleton-containing compound include adamantane derivatives such as 1-adamantanecarboxylic acid, 2-adamantanone, and 1-adamantanecarboxylic acid t-butyl; Deoxycholic acid esters such as t-butyl deoxycholic acid, t-butoxycarbonylmethyl deoxycholic acid, 2-ethoxyethyl deoxycholic acid; Lithocholic acid esters such as tert-butyl lithocholic acid, tert-butoxycarbonylmethyl lithocholic acid, 2-ethoxyethyl lithocholic acid; 3- [2-hydroxy-2,2-bis (trifluoromethyl) ethyl] tetracyclo [4.4.0.1 2,5 .
- the said radiation sensitive resin composition contains an alicyclic skeleton containing compound, as an upper limit of content of an alicyclic skeleton containing compound, 5 mass parts is with respect to 100 mass parts of [A] polymer components. preferable.
- the sensitizer exhibits the effect of increasing the amount of acid generated from the [B] acid generator component and the like, and has the effect of improving the “apparent sensitivity” of the radiation-sensitive resin composition.
- the sensitizer include carbazoles, acetophenones, benzophenones, naphthalenes, phenols, biacetyl, eosin, rose bengal, pyrenes, anthracenes, phenothiazines and the like.
- a sensitizer as an upper limit of content of a sensitizer, 2 mass parts is preferable with respect to 100 mass parts of [A] polymer components.
- the radiation sensitive resin composition includes, for example, [A] a polymer component, [B] an acid generator component, and optionally [C] an acid diffusion controller, [D] an optional component such as a solvent in a predetermined ratio. It can be prepared by mixing and preferably filtering the obtained mixture, for example, with a filter having a pore diameter of about 0.2 ⁇ m.
- a filter having a pore diameter of about 0.2 ⁇ m As a minimum of solid concentration of the radiation sensitive resin composition, 0.1 mass% is preferred, 0.5 mass% is more preferred, and 1 mass% is still more preferred. As an upper limit of the said solid content concentration, 50 mass% is preferable, 20 mass% is more preferable, and 5 mass% is further more preferable.
- ⁇ Resist pattern formation method> a step of applying the radiation-sensitive resin composition to one surface of a substrate (hereinafter also referred to as “coating step”) and a resist film obtained by the coating step are exposed. And a step of developing the exposed resist film (hereinafter also referred to as “developing step”).
- the resist pattern forming method since the radiation-sensitive resin composition is used, LWR and CDU are small, resolution is high, and cross-sectional rectangularity is excellent while exhibiting excellent exposure margin. A resist pattern can be formed. Hereinafter, each step will be described.
- the radiation sensitive resin composition is applied to one surface of the substrate.
- a resist film is formed.
- the substrate on which the resist film is formed include conventionally known ones such as a silicon wafer, silicon dioxide, and a wafer coated with aluminum.
- an organic or inorganic antireflection film disclosed in Japanese Patent Publication No. 6-12452 and Japanese Patent Application Laid-Open No. 59-93448 may be formed on the substrate.
- the coating method include spin coating, spin coating, and roll coating.
- pre-baking (PB) may be performed as needed to volatilize the solvent in the coating film. As a minimum of the temperature of PB, 60 degreeC is preferable and 80 degreeC is more preferable.
- the lower limit of the PB time is preferably 5 seconds, and more preferably 10 seconds.
- the upper limit of the time is preferably 600 seconds, and more preferably 300 seconds.
- 10 nm is preferable and 20 nm is more preferable.
- 1,000 nm is preferable, and 500 nm is more preferable.
- an immersion protective film that is insoluble in the immersion liquid may be provided.
- a solvent peeling type protective film that peels off with a solvent before the developing process see JP 2006-227632 A
- a developer peeling type protective film that peels off simultaneously with development in the developing process International Publication No. 2005/069096 and International Publication No. 2006/035790
- the resist film obtained by the coating step is exposed.
- This exposure is performed by irradiating exposure light through a photomask (in some cases through an immersion medium such as water).
- electromagnetic waves such as visible light, ultraviolet light, far ultraviolet light, extreme ultraviolet light (EUV), X-rays and ⁇ rays; charged particle beams such as electron beams and ⁇ rays, depending on the line width of the target pattern.
- EUV extreme ultraviolet light
- charged particle beams such as electron beams and ⁇ rays, depending on the line width of the target pattern.
- EUV and electron beams are preferable, ArF excimer laser light (wavelength 193 nm), KrF excimer laser light (wavelength 248 nm), EUV and electron beams are more preferable, ArF excimer laser light, EUV and electron beams are more preferable. Further preferred are EUV and electron beam.
- the immersion liquid to be used include water and a fluorine-based inert liquid.
- the immersion liquid is preferably a liquid that is transparent to the exposure wavelength and has a refractive index with a temperature coefficient that is as small as possible so as to minimize distortion of the optical image projected onto the film.
- water it is preferable to use water from the viewpoints of availability and easy handling in addition to the above-described viewpoints.
- an additive that reduces the surface tension of water and increases the surface activity may be added in a small proportion. This additive is preferably one that does not dissolve the resist film on the wafer and can ignore the influence on the optical coating on the lower surface of the lens.
- the water used is preferably distilled water.
- PEB post exposure bake
- This PEB can increase the difference in solubility in the developer between the exposed portion and the unexposed portion.
- 50 degreeC is preferable and 80 degreeC is more preferable.
- 80 degreeC is more preferable.
- 180 degreeC is preferable and 130 degreeC is more preferable.
- the lower limit of the PEB time is preferably 5 seconds, and more preferably 10 seconds.
- the upper limit of the time is preferably 600 seconds, and more preferably 300 seconds.
- the radiation sensitive resin composition described above since the radiation sensitive resin composition described above is used, shrinkage of the resist film during PEB can be suppressed.
- the exposed resist film is developed. Thereby, a predetermined resist pattern can be formed. After development, it is common to wash with water or a rinse solution such as alcohol and then dry.
- the development method in the development step may be alkali development or organic solvent development.
- examples of the developer used for development include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, and di-n-.
- TMAH tetramethylammonium hydroxide
- pyrrole pyrrole
- piperidine choline
- 1,8-diazabicyclo- [5.4.0] -7-undecene 1,8-diazabicyclo- [4.3.0] -5-nonene and the like
- an alkaline aqueous solution in which at least one kind of alkaline compound is dissolved.
- a TMAH aqueous solution is preferable, and a 2.38 mass% TMAH aqueous solution is more preferable.
- examples of the developer include hydrocarbon solvents, ether solvents, ester solvents, ketone solvents, alcohol solvents, and other organic solvents, and solvents containing the above organic solvents.
- organic solvent the 1 type (s) or 2 or more types of the solvent enumerated as the [C] solvent of the above-mentioned radiation sensitive resin composition are mentioned, for example.
- ester solvents and ketone solvents are preferable.
- the ester solvent an acetate solvent is preferable, and n-butyl acetate is more preferable.
- the ketone solvent is preferably a chain ketone, more preferably 2-heptanone.
- 80 mass% is preferred, 90 mass% is more preferred, 95 mass% is still more preferred, and 99 mass% is especially preferred.
- components other than the organic solvent in the developer include water and silicone oil.
- a developing method for example, a method in which a substrate is immersed in a tank filled with a developer for a certain period of time (dip method), a method in which the developer is raised on the surface of the substrate by surface tension and is left stationary for a certain time (paddle method) ), A method of spraying the developer on the substrate surface (spray method), a method of continuously applying the developer while scanning the developer coating nozzle on the substrate rotating at a constant speed (dynamic dispensing method) Etc.
- the compounds (M-1) to (M-6) are structural units (I)
- the compounds (M-7) to (M-9) are structural units (II)
- (M-10) to (M M-16) gives the structural unit (III), respectively.
- (M-17) to (M-21) give other structural units.
- the polymerization reaction solution was dropped into 1,000 g of n-hexane to coagulate and purify the polymer.
- 150 g of propylene glycol monomethyl ether was added to the above polymer, and further 150 g of methanol, 25 g of triethylamine and 5 g of water were added, and a hydrolysis reaction was performed for 8 hours while refluxing at the boiling point.
- the solvent and triethylamine were distilled off under reduced pressure, and the resulting polymer was dissolved in 150 g of acetone, then dropped into 2,000 g of water and solidified, and the resulting white powder was collected by filtration at 50 ° C.
- the white powdery polymer (A-1) was obtained by drying for 17 hours (yield 68.3 g, yield 68%). Mw of the polymer (A-1) was 6,700, and Mw / Mn was 1.54. As a result of 13 C-NMR analysis, the content ratio of each structural unit derived from (M-1), p-hydroxystyrene and (M-10) was 20.5 mol%, 40.0 mol% and It was 39.5 mol%.
- Mw of the polymer (A-5) was 6,900, and Mw / Mn was 1.55.
- the content ratio of each structural unit derived from (M-5), (M-9), (M-15) and (M-19) was 21.7 mol%, respectively. They were 20.5 mol%, 53.6 mol%, and 4.2 mol%.
- Example 1 (Preparation of radiation-sensitive resin composition (J-1)) [A] 100 parts by mass of (A-1) as a polymer component, [B1] 10 parts by mass of (B-9) as an acid generator, [B2] 7 parts by mass of (B-1) as an acid generator [C] 5 parts by weight of (C-1) as an acid diffusion control agent, and (D-1) 4,510 parts by weight and (D-2) 1,930 parts by weight of [D] solvent, The resulting mixture was filtered through a 20 nm membrane filter to prepare a radiation sensitive resin composition (J-1).
- Examples 2 to 29 and Comparative Examples 1 to 7 Preparation of radiation-sensitive resin compositions (J-2) to (J-29) and (CJ-1) to (CJ-7)) Except that the components of the types and contents shown in Table 2 and Table 3 below were used, the same operation as in Example 1 was carried out to prepare the radiation sensitive resin compositions (J-2) to (J-29) and ( CJ-1) to (CJ-7) were prepared. “-” In Table 2 and Table 3 indicates that the corresponding component was not used.
- a resist pattern that exhibits excellent exposure margin, low LWR and CDU, high resolution, and excellent cross-sectional rectangularity is formed. can do. Therefore, these can be suitably used for manufacturing semiconductor devices that are expected to be further miniaturized in the future.
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Abstract
Description
当該感放射線性樹脂組成物は、[A]重合体成分と[B]酸発生剤成分とを含有する。当該感放射線性樹脂組成物は、好適成分として、[C]酸拡散制御剤、[D]溶媒及び[A]重合体成分よりもフッ素原子の質量含有率が大きい重合体(以下、「[E]重合体」ともいう)を含有していてもよく、本発明の効果を損なわない範囲において、その他の任意成分を含有していてもよい。
[A]重合体成分は、同一又は異なる重合体中に、構造単位(I)、構造単位(II)及び構造単位(III)を有する重合体成分である。
構造単位(I)は、下記式(1)で表される基を含む構造単位である。
シクロプロパン構造、シクロブタン構造、シクロペンタン構造、シクロヘキサン構造、シクロヘプタン構造、シクロオクタン構造等の単環の飽和脂環構造;
ノルボルナン構造、アダマンタン構造、トリシクロデカン構造、テトラシクロドデカン構造等の多環の飽和脂環構造;
シクロプロペン構造、シクロブテン構造、シクロペンテン構造、シクロヘキセン構造、シクロヘプテン構造、シクロオクテン構造等の単環の不飽和脂環構造;
ノルボルネン構造、トリシクロデセン構造、テトラシクロドデセン構造等の多環の不飽和脂環構造などが挙げられる。これらの中で、単環の飽和脂環構造及び多環の飽和脂環構造が好ましい。
メチル基、エチル基、プロピル記、ブチル基等のアルキル基;
エテニル基、プロペニル基、ブテニル基のアルケニル基;
エチニル基、プロピニル基、ブチニル基等のアルキニル基などが挙げられる。
シクロペンチル基、シクロヘキシル基等の単環の脂環式飽和炭化水素基;
シクロペンテニル基、シクロヘキセニル基等の単環の脂環式不飽和炭化水素基;
ノルボルニル基、アダマンチル基、トリシクロデシル基等の多環の脂環式飽和炭化水素基;
ノルボルネニル基、トリシクロデセニル等の多環の脂環式不飽和炭化水素基などが挙げられる。
フェニル基、トリル基基、キシリル基、ナフチル基、アントリル基等のアリール基;
ベンジル基、フェネチル基、ナフチルメチル基等のアラルキル基などが挙げられる。
上記式(i-1)中、R8は、水素原子、フッ素原子、メチル基又はトリフルオロメチル基である。
上記式(i-2)中、R9は、単結合、-O-又は炭素数1~20の2価の有機基である。R10は、水素原子又は炭素数1~20の1価の有機基である。
構造単位(II)は、芳香環に結合した水酸基を含む構造単位である。
構造単位(III)は、酸解離性基を含む構造単位である。「酸解離性基」とは、カルボキシ基、ヒドロキシ基等の水素原子を置換する基であって、酸の作用により解離する基をいう。当該感放射線性樹脂組成物は、[A]重合体成分が構造単位(III)を有することで、感度がより高まり、その結果、LWR性能等をより向上させることができる。
上記式(iii-2)中、R18は、水素原子又はメチル基である。L1は、単結合、-CCOO-又は-CONH-である。R19、R20及びR21は、それぞれ独立して、水素原子、炭素数1~20の1価の炭化水素基又は炭素数1~20の1価のオキシ炭化水素基である。
メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、i-ブチル基、sec-ブチル基、t-ブチル基、ペンチル基等のアルキル基;
エテニル基、プロペニル基、ブテニル基、ペンテニル基等のアルケニル基;
エチニル基、プロピニル基、ブチニル基、ペンチニル基等のアルキニル基等が挙げられる。
シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等の単環の脂環式飽和炭化水素基;
ノルボルニル基、アダマンチル基、トリシクロデシル基、テトラシクロドデシル基等の多環の脂環式飽和炭化水素基;
シクロプロペニル基、シクロブテニル基、シクロペンテニル基、シクロヘキセニル基等の単環の脂環式不飽和炭化水素基;
ノルボルネニル基、トリシクロデセニル基等の多環の脂環式飽和炭化水素基などが挙げられる。
フェニル基、トリル基、キシリル基、ナフチル基、アントリル基等のアリール基;
ベンジル基、フェネチル基、ナフチルメチル基、アントリルメチル基等のアラルキル基等が挙げられる。
シクロプロパン構造、シクロブタン構造、シクロペンタン構造、シクロヘキサン構造、シクロヘプタン構造、シクロオクタン構造等の単環の脂環構造;
ノルボルナン構造、アダマンタン構造、トリシクロデカン構造、テトラシクロドデカン構造等の多環の脂環構造などが挙げられる。
構造単位(III-2)としては下記式(iii-2-1)で表される構造単位(以下、「構造単位(III-2-1)」ともいう)が好ましい。
上記式(iii-2-1)中、R18~R21は、上記式(iii-2)と同義である。
構造単位(IV)は、ラクトン構造、環状カーボネート構造、スルトン構造又はこれらの組み合わせを含む構造単位である。[A]重合体成分は、構造単位(IV)をさらに有することで、現像液への溶解性をより調整することができ、その結果、当該感放射線性樹脂組成物のLWR性能等をより向上させることができる。また、当該感放射線性樹脂組成物から形成されるレジストパターンと基板との密着性を向上させることができる。
構造単位(V)は、アルコール性水酸基を含む構造単位である。[A]重合体成分は、構造単位(V)をさらに有することで、現像液への溶解性をより調整することができ、その結果、当該感放射線性樹脂組成物のLWR性能等をより向上させることができる。また、当該感放射線性樹脂組成物から形成されるレジストパターンと基板との密着性を向上させることができる。
[A]重合体成分は、同一又は異なる重合体中に、構造単位(I)~(V)以外のその他の構造単位を有していてもよい。その他の構造単位としては例えば2-シアノメチルアダマンタン-2-イル(メタ)アクリレートに由来する構造単位等のシアノ基、ニトロ基又はスルホンアミド基を含む構造単位、2,2,2-トリフルオロエチル(メタ)アクリレートに由来する構造単位、1,1,1,3,3,3-ヘキサフルオロプロパン-2-イル(メタ)アクリレートに由来する構造単位等のフッ素原子を含む構造単位、スチレンに由来する構造単位、ビニルナフタレンに由来する構造単位、n-ペンチル(メタ)アクリレートに由来する構造単位等の非酸解離性の炭化水素基を含む構造単位等が挙げられる。
[A]重合体成分を構成する重合体は、例えば各構造単位を与える単量体を、ラジカル重合開始剤等を用い、適当な溶媒中で重合することにより合成できる。
n-ペンタン、n-ヘキサン、n-ヘプタン、n-オクタン、n-ノナン、n-デカン等のアルカン類;
シクロヘキサン、シクロヘプタン、シクロオクタン、デカリン、ノルボルナン等のシクロアルカン類;
ベンゼン、トルエン、キシレン、エチルベンゼン、クメン等の芳香族炭化水素類;
クロロブタン類、ブロモヘキサン類、ジクロロエタン類、ヘキサメチレンジブロミド、クロロベンゼン等のハロゲン化炭化水素類;
酢酸エチル、酢酸n-ブチル、酢酸i-ブチル、プロピオン酸メチル等の飽和カルボン酸エステル類;
アセトン、ブタノン、4-メチル-2-ペンタノン、2-ヘプタノン等のケトン類;
テトラヒドロフラン、ジメトキシエタン類、ジエトキシエタン類等のエーテル類;
メタノール、エタノール、1-プロパノール、2-プロパノール、4-メチル-2-ペンタノール等のアルコール類等が挙げられる。これらの重合に使用される溶媒は、1種単独で又は2種以上を併用してもよい。
GPCカラム:東ソー社の「G2000HXL」2本、「G3000HXL」1本及び「G4000HXL」1本
カラム温度:40℃
溶出溶媒:テトラヒドロフラン(和光純薬工業社)
流速:1.0mL/分
試料濃度:1.0質量%
試料注入量:100μL
検出器:示差屈折計
標準物質:単分散ポリスチレン
[B]酸発生剤成分は、[B1]酸発生剤及び[B2]酸発生剤を含む。[B]酸発生剤成分は、[B1]酸発生剤及び[B2]酸発生剤以外の他の酸発生剤を含んでいてもよい。[B]酸発生剤成分は、露光により酸を発生する物質である。この発生した酸により[A]重合体成分等が有する酸解離性基が解離してカルボキシ基、ヒドロキシ基等が生じ、[A]重合体成分等の現像液への溶解性が変化するため、当該感放射線性樹脂組成物からレジストパターンを形成することができる。
[B1]酸発生剤は、スルホ基に隣接する炭素原子を有しこの炭素原子にフッ素原子若しくは1価のフッ素化炭化水素基が結合するスルホン酸(以下、「スルホン酸(I)」ともいう)を発生する酸発生剤である。スルホン酸(I)は、例えば下記式(A)で表される基を有するスルホン酸である。
シクロヘキサン構造、シクロヘプタン構造、シクロオクタン構造、シクロノナン構造、シクロデカン構造、シクロドデカン構造等の単環の飽和脂環構造;
シクロヘキセン構造、シクロヘプテン構造、シクロオクテン構造、シクロデセン構造等の単環の不飽和脂環構造;
ノルボルナン構造、アダマンタン構造、トリシクロデカン構造、テトラシクロドデカン構造等の多環の飽和脂環構造;
ノルボルネン構造、トリシクロデセン構造等の多環の不飽和脂環構造等が挙げられる。
ヘキサノラクトン構造、ノルボルナンラクトン構造等のラクトン構造;
ヘキサノスルトン構造、ノルボルナンスルトン構造等のスルトン構造;
オキサシクロヘプタン構造、オキサノルボルナン構造等の酸素原子含有複素環構造;
アザシクロヘキサン構造、ジアザビシクロオクタン構造、アザデカリン構造等の窒素原子含有複素環構造;
チアシクロヘキサン構造、チアノルボルナン構造等のイオウ原子含有複素環構造などが挙げられる。
ピラン構造、ベンゾフラン構造、ベンゾピラン構造等の酸素原子含有複素環構造;
ピリジン構造、ピリミジン構造、インドール構造等の窒素原子含有複素環構造などが挙げられる。
メチル基、エチル基、n-プロピル基、n-ブチル基等の直鎖状アルキル基;
i-プロピル基、i-ブチル基、sec-ブチル基、t-ブチル基等の分岐状アルキル基などが挙げられる。
フェニル基、トリル基、キシリル基、メシチル基、ナフチル基等のアリール基;
ベンジル基、フェネチル基等のアラルキル基などが挙げられる。
[B2]酸発生剤は、スルホ基に隣接する炭素原子とこの炭素原子に隣接する炭素原子とを有しこれらの炭素原子のいずれにもフッ素原子若しくは1価のフッ素化炭化水素基が結合していないスルホン酸(以下、「スルホン酸(II)」ともいう)、又はカルボキシ基に隣接する炭素原子を有しこの炭素原子にフッ素原子若しくは1価のフッ素化炭化水素基が結合するカルボン酸(以下、「カルボン酸(II)」ともいう)を発生する酸発生剤である。
他の酸発生剤としては、[B1]酸発生剤及び[B2]酸発生剤以外のオニウム塩化合物、N-スルホニルイミドオキシ化合物、スルホンイミド化合物、ハロゲン含有化合物、ジアゾケトン化合物等が挙げられる。他の酸発生剤の具体例としては、例えば特開2009-134088号公報の段落[0080]~[0113]に記載されている化合物等が挙げられる。他の酸発生剤は、1種又は2種以上を用いることができる。
当該感放射線性樹脂組成物は、必要に応じて、[C]酸拡散制御剤(但し、[B]酸発生剤成分に該当するものを除く)を含有してもよい。[C]酸拡散制御剤としては、窒素含有化合物、露光により感光し弱酸を発生する光崩壊性塩基等が挙げられる。[C]酸拡散制御剤は、露光により[B]酸発生剤成分から生じる酸のレジスト膜中における拡散現象を制御し、非露光領域における好ましくない化学反応を抑制する効果を奏する。また、感放射線性樹脂組成物の貯蔵安定性が向上すると共に、レジストとしての解像度がより向上する。さらに、露光から現像処理までの引き置き時間の変動によるレジストパターンの線幅変化を抑えることができ、プロセス安定性に優れた感放射線性樹脂組成物が得られる。
[D]溶媒は、少なくとも[A]重合体成分、[B]酸発生剤成分及び所望により含有される[C]酸拡散制御剤等を溶解又は分散可能な溶媒であれば特に限定されない。
4-メチル-2-ペンタノール、n-ヘキサノール等の炭素数1~18の脂肪族モノアルコール系溶媒;
シクロヘキサノール等の炭素数3~18の脂環式モノアルコール系溶媒;
1,2-プロピレングリコール等の炭素数2~18の多価アルコール系溶媒;
プロピレングリコールモノメチルエーテル等の炭素数3~19の多価アルコール部分エーテル系溶媒などが挙げられる。
ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジペンチルエーテル、ジイソアミルエーテル、ジヘキシルエーテル、ジヘプチルエーテル等のジアルキルエーテル系溶媒;
テトラヒドロフラン、テトラヒドロピラン等の環状エーテル系溶媒;
ジフェニルエーテル、アニソール等の芳香環含有エーテル系溶媒などが挙げられる。
アセトン、メチルエチルケトン、メチル-n-プロピルケトン、メチル-n-ブチルケトン、ジエチルケトン、メチル-iso-ブチルケトン、2-ヘプタノン、エチル-n-ブチルケトン、メチル-n-ヘキシルケトン、ジ-iso-ブチルケトン、トリメチルノナノン等の鎖状ケトン系溶媒:
シクロペンタノン、シクロヘキサノン、シクロヘプタノン、シクロオクタノン、メチルシクロヘキサノン等の環状ケトン系溶媒:
2,4-ペンタンジオン、アセトニルアセトン、アセトフェノン等が挙げられる。
N,N’-ジメチルイミダゾリジノン、N-メチルピロリドン等の環状アミド系溶媒;
N-メチルホルムアミド、N,N-ジメチルホルムアミド、N,N-ジエチルホルムアミド、アセトアミド、N-メチルアセトアミド、N,N-ジメチルアセトアミド、N-メチルプロピオンアミド等の鎖状アミド系溶媒などが挙げられる。
酢酸n-ブチル、乳酸エチル等のモノカルボン酸エステル系溶媒;
プロピレングリコールアセテート等の多価アルコールカルボキシレート系溶媒;
プロピレングリコールモノメチルエーテルアセテート等の多価アルコール部分エーテルカルボキシレート系溶媒;
シュウ酸ジエチル等の多価カルボン酸ジエステル系溶媒;
ジメチルカーボネート、ジエチルカーボネート等のカーボネート系溶媒などが挙げられる。
n-ペンタン、n-ヘキサン等の炭素数5~12の脂肪族炭化水素系溶媒;
トルエン、キシレン等の炭素数6~16の芳香族炭化水素系溶媒等が挙げられる。
[E]重合体は、[A]重合体成分よりもフッ素原子の質量含有率が大きい重合体である。当該感放射線性樹脂組成物は、例えば撥水性添加剤として[E]重合体を含有することができる。
構造単位(Ea)は、下記式(8a)で表される構造単位である。[E]重合体は、構造単位(Ea)を有することでフッ素原子含有率を調整することができる。
2,2,2-トリフルオロエチル(メタ)アクリル酸エステル等の直鎖部分フッ素化アルキル(メタ)アクリル酸エステル;
1,1,1,3,3,3-ヘキサフルオロi-プロピル(メタ)アクリル酸エステル等の分岐鎖部分フッ素化アルキル(メタ)アクリル酸エステル;
パーフルオロエチル(メタ)アクリル酸エステル等の直鎖パーフルオロアルキル(メタ)アクリル酸エステル;
パーフルオロi-プロピル(メタ)アクリル酸エステル等の分岐鎖パーフルオロアルキル(メタ)アクリル酸エステルなどのフッ素化鎖状炭化水素基を有する(メタ)アクリル酸エステル;
パーフルオロシクロヘキシルメチル(メタ)アクリル酸エステル、モノフルオロシクロペンチル(メタ)アクリル酸エステル、パーフルオロシクロペンチル(メタ)アクリル酸エステル等の単環のフッ素化脂環式飽和炭化水素基を有する(メタ)アクリル酸エステル;
フルオロノルボルニル(メタ)アクリル酸エステル等の多環のフッ素化脂環式飽和炭化水素基を有する(メタ)アクリル酸エステルなどのフッ素化脂環式炭化水素基を有する(メタ)アクリル酸エステルなどが挙げられる。これらの中で、フッ素化鎖状炭化水素基を有する(メタ)アクリル酸エステルが好ましく、直鎖部分フッ素化アルキル(メタ)アクリル酸エステルがより好ましく、2,2,2-トリフルオロエチル(メタ)アクリル酸エステルがさらに好ましい。
構造単位(Eb)は、下記式(8b)で表される構造単位である。[E]重合体は、構造単位(Eb)を有することで疎水性が上がるため、当該感放射線性樹脂組成物から形成されたレジスト膜表面の動的接触角をさらに向上させることができる。
[E]重合体は、構造単位(Ea)及び(Eb)以外にも、酸解離性基を含む構造単位(以下、「構造単位(Ec)」ともいう。)を有してもよい(但し、構造単位(Eb)に該当するものを除く)。[E]重合体が構造単位(Ec)を有することで、得られるレジストパターンの形状がより良好になる。構造単位(Ec)としては、上記[A]重合体成分における構造単位(III)等が挙げられる。
当該感放射線性樹脂組成物は、上記[A]~[E]成分以外にも、その他の任意成分を含有していてもよい。その他の任意成分としては、例えば偏在化促進剤、界面活性剤、脂環式骨格含有化合物、増感剤等が挙げられる。これらのその他の任意成分は、それぞれ1種又は2種以上を併用してもよい。
偏在化促進剤は、当該感放射線性樹脂組成物が[E]重合体を含有する場合等に、[E]重合体を、より効率的にレジスト膜表面に偏析させる効果を有するものである。当該感放射線性樹脂組成物に偏在化促進剤を含有させることで、[E]重合体の添加量を従来よりも少なくすることができる。従って、LWR性能等を損なうことなく、レジスト膜から液浸液への成分の溶出をさらに抑制することや、高速スキャンにより液浸露光をより高速に行うことが可能になり、結果としてウォーターマーク欠陥等の液浸由来欠陥を抑制するレジスト膜表面の疎水性を向上させることができる。このような偏在化促進剤として用いることができるものとしては、比誘電率が30以上200以下で、1気圧における沸点が100℃以上の低分子化合物を挙げることができる。このような化合物としては、具体的には、ラクトン化合物、カーボネート化合物、ニトリル化合物、多価アルコール等が挙げられる。
界面活性剤は、塗工性、ストリエーション、現像性等を改良する効果を奏する。界面活性剤としては、例えばポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンn-オクチルフェニルエーテル、ポリオキシエチレンn-ノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等のノニオン系界面活性剤;市販品としては、KP341(信越化学工業社)、ポリフローNo.75、同No.95(以上、共栄社化学社)、エフトップEF301、同EF303、同EF352(以上、トーケムプロダクツ社)、メガファックF171、同F173(以上、DIC社)、フロラードFC430、同FC431(以上、住友スリーエム社)、アサヒガードAG710、サーフロンS-382、同SC-101、同SC-102、同SC-103、同SC-104、同SC-105、同SC-106(以上、旭硝子工業社)等が挙げられる。当該感放射線性樹脂組成物が界面活性剤を含有する場合、界面活性剤の含有量の上限としては、[A]重合体成分100質量部に対して、2質量部が好ましい。
脂環式骨格含有化合物は、ドライエッチング耐性、パターン形状、基板との接着性等を改善する効果を奏する。脂環式骨格含有化合物としては、例えば
1-アダマンタンカルボン酸、2-アダマンタノン、1-アダマンタンカルボン酸t-ブチル等のアダマンタン誘導体類;
デオキシコール酸t-ブチル、デオキシコール酸t-ブトキシカルボニルメチル、デオキシコール酸2-エトキシエチル等のデオキシコール酸エステル類;
リトコール酸t-ブチル、リトコール酸t-ブトキシカルボニルメチル、リトコール酸2-エトキシエチル等のリトコール酸エステル類;
3-〔2-ヒドロキシ-2,2-ビス(トリフルオロメチル)エチル〕テトラシクロ[4.4.0.12,5.17,10]ドデカン、2-ヒドロキシ-9-メトキシカルボニル-5-オキソ-4-オキサ-トリシクロ[4.2.1.03,7]ノナン等が挙げられる。当該感放射線性樹脂組成物が脂環式骨格含有化合物を含有する場合、脂環式骨格含有化合物の含有量の上限としては、[A]重合体成分100質量部に対して、5質量部が好ましい。
増感剤は、[B]酸発生剤成分等からの酸の生成量を増加する作用を示すものであり、当該感放射線性樹脂組成物の「みかけの感度」を向上させる効果を奏する。増感剤としては、例えばカルバゾール類、アセトフェノン類、ベンゾフェノン類、ナフタレン類、フェノール類、ビアセチル、エオシン、ローズベンガル、ピレン類、アントラセン類、フェノチアジン類等が挙げられる。当該感放射線性樹脂組成物が増感剤を含有する場合、増感剤の含有量の上限としては、[A]重合体成分100質量部に対して、2質量部が好ましい。
当該感放射線性樹脂組成物は、例えば[A]重合体成分、[B]酸発生剤成分、必要に応じて[C]酸拡散制御剤、[D]溶媒等の任意成分を所定の割合で混合し、好ましくは得られた混合物を、例えば孔径0.2μm程度のフィルター等でろ過することにより調製することができる。当該感放射線性樹脂組成物の固形分濃度の下限としては、0.1質量%が好ましく、0.5質量%がより好ましく、1質量%がさらに好ましい。上記固形分濃度の上限としては、50質量%が好ましく、20質量%がより好ましく、5質量%がさらに好ましい。
当該レジストパターン形成方法は、基板の一方の面に、当該感放射線性樹脂組成物を塗工する工程(以下、「塗工工程」ともいう)と、上記塗工工程により得られるレジスト膜を露光する工程(以下、「露光工程」ともいう)と、上記露光されたレジスト膜を現像する工程(以下、「現像工程」ともいう)とを備える。
本工程では、基板の一方の面に、当該感放射線性樹脂組成物を塗工する。これにより、レジスト膜が形成される。このレジスト膜を形成する基板としては、例えばシリコンウェハ、二酸化シリコン、アルミニウムで被覆されたウェハ等の従来公知のもの等が挙げられる。また、例えば特公平6-12452号公報や特開昭59-93448号公報等に開示されている有機系又は無機系の反射防止膜を基板上に形成してもよい。塗工方法としては、例えば回転塗工(スピンコーティング)、流延塗工、ロール塗工等が挙げられる。塗工した後に、必要に応じて、塗膜中の溶媒を揮発させるため、プレベーク(PB)を行ってもよい。PBの温度の下限としては、60℃が好ましく、80℃がより好ましい。上記温度の上限としては、140℃が好ましく、120℃がより好ましい。PBの時間の下限としては、5秒が好ましく、10秒がより好ましい。上記時間の上限としては、600秒が好ましく、300秒がより好ましい。形成されるレジスト膜の平均厚みの下限としては、10nmが好ましく、20nmがより好ましい。上記平均厚みの上限としては、1,000nmが好ましく、500nmがより好ましい。
本工程では、上記塗工工程により得られるレジスト膜を露光する。この露光は、フォトマスクを介して(場合によっては、水等の液浸媒体を介して)露光光を照射することにより行う。露光光としては、目的とするパターンの線幅に応じて、例えば可視光線、紫外線、遠紫外線、極端紫外線(EUV)、X線、γ線等の電磁波;電子線、α線等の荷電粒子線などが挙げられる。これらの中でも、遠紫外線、EUV及び電子線が好ましく、ArFエキシマレーザー光(波長193nm)、KrFエキシマレーザー光(波長248nm)、EUV及び電子線がより好ましく、ArFエキシマレーザー光、EUV及び電子線がさらに好ましく、EUV及び電子線が特に好ましい。
本工程では、上記露光されたレジスト膜を現像する。これにより、所定のレジストパターンを形成することができる。現像後は、水又はアルコール等のリンス液で洗浄し、乾燥することが一般的である。現像工程における現像方法は、アルカリ現像であっても、有機溶媒現像であってもよい。
GPCカラム(東ソー社の「G2000HXL」2本、「G3000HXL」1本、「G4000HXL」1本)を用い、流量:1.0mL/分、溶出溶媒:テトラヒドロフラン、試料濃度:1.0質量%、試料注入量:100μL、カラム温度:40℃、検出器:示差屈折計の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィ(GPC)により測定した。分散度(Mw/Mn)は、Mw及びMnの測定結果より算出した。
核磁気共鳴装置(日本電子社の「JNM-ECX400」)を用い、測定溶媒として重ジメチルスルホキシドを使用して、各重合体における各構造単位の含有割合(モル%)を求める分析を行った。
[A]重合体成分の合成に用いた単量体について以下に示す。
上記化合物(M-1)34.42g(20モル%)、化合物(M-7)33.40g(40モル%)、化合物(M-10)32.17g(40モル%)、ラジカル重合開始剤としてのAIBN4.23g(単量体の合計に対して5モル%)及び連鎖移動剤としてのt-ドデシルメルカプタン1.56g(単量体の合計に対して1.5モル%)をプロピレングリコールモノメチルエーテル200gに溶解した後、窒素雰囲気下、反応温度を70℃に保持して、9時間重合させた。重合反応終了後、重合反応液を1,000gのn-ヘキサン中に滴下して、重合体を凝固精製した。次に、上記重合体に、プロピレングリコールモノメチルエーテル150gを加え、さらにメタノール150g、トリエチルアミン25g及び水5gを加えて、沸点にて還流させながら、8時間加水分解反応を行った。反応終了後、溶媒及びトリエチルアミンを減圧留去し、得られた重合体をアセトン150gに溶解した後、2,000gの水中に滴下して凝固させ、生成した白色粉末をろ取し、50℃で17時間乾燥させて白色粉末状の重合体(A-1)を得た(収量68.3g、収率68%)。重合体(A-1)のMwは6,700、Mw/Mnは1.54であった。また、13C-NMR分析の結果、(M-1)、p-ヒドロキシスチレン及び(M-10)に由来する各構造単位の含有割合は、それぞれ20.5モル%、40.0モル%及び39.5モル%であった。
下記表1に示す種類及び使用量の単量体を用いた以外は、合成例1と同様の操作を行うことによって、重合体(A-2)~(A-4)、(A-7)、(A-9)~(A-11)、(A-14)及び(A-16)を合成した。得られた重合体の各構造単位の含有割合(モル%)、収率(%)、Mw及びMw/Mnについて、表1に合わせて示す。
上記化合物(M-5)33.09g(20モル%)、化合物(M-9)14.23g(20モル%)、化合物(M-15)47.95g(55モル%)、化合物(M-19)4.72g(5モル%)を2-ブタノン200gに溶解し、ラジカル重合開始剤としてのAIBN3.28g(単量体の合計に対して5モル%)を添加して単量体溶液を調製した。次に、100gの2-ブタノンを入れた500mLの三口フラスコを30分窒素パージした後、攪拌しながら80℃に加熱し、上記調製した単量体溶液を滴下漏斗にて3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した。重合反応終了後、重合反応液を水冷して30℃以下に冷却した。2,000gのメタノール中に冷却した重合反応液を投入し、析出した白色粉末をろ別した。ろ別した白色粉末を80gのメタノールで2回洗浄した後、ろ別し、50℃で17時間乾燥させて白色粉末状の重合体(A-5)を得た(収量72.8g、収率73%)。重合体(A-5)のMwは6,900、Mw/Mnは1.55であった。また、13C-NMR分析の結果、(M-5)、(M-9)、(M-15)及び(M-19)に由来する各構造単位の含有割合は、それぞれ21.7モル%、20.5モル%、53.6モル%及び4.2モル%であった。
下記表1に示す種類及び使用量の単量体を用いた以外は、合成例1と同様の操作を行うことによって、重合体(A-8)、(A-12)、(A-13)及び(A-15)を合成した。得られた重合体の各構造単位の含有割合(モル%)、収率(%)、Mw及びMw/Mnについて、表1に合わせて示す。
プロピレングリコールモノメチルエーテル100gを窒素気流下、80℃に加熱した。この液を攪拌しながら、化合物(M-2)39.34g(25モル%)、化合物(M-9)23.35g(30モル%)、化合物(M-16)33.59g(40モル%)、化合物(M-18)3.72g(5モル%)、プロピレングリコールモノメチルエーテル200g及び2,2’-アゾビスイソ酪酸ジメチル(和光純薬工業社の「V-601」)5.03g(単量体の合計に対して5モル%)の混合溶液を2時間かけて滴下した。滴下終了後、80℃でさらに4時間攪拌した。反応液を放冷後、多量のヘキサン/酢酸エチルで再沈殿させ、得られた沈殿物を真空乾燥させて重合体(A-6)を得た(収量68.5g、収率69%)。重合体(A-6)のMwは7,200、Mw/Mnは1.52であった。また、13C-NMR分析の結果、(M-2)、(M-9)、(M-16)及び(M-18)に由来する各構造単位の含有割合は、それぞれ24.2モル%、30.4モル%、40.4モル%及び5.0モル%であった。
感放射線性樹脂組成物の調製に用いた[A]重合体成分以外の成分について、以下に示す。
各構造式を以下に示す。
[B2]酸発生剤:化合物(B-1)~(B-8)
[B1]酸発生剤:化合物(B-9)~(B-14)
各構造式を以下に示す。
C-1:トリフェニルスルホニウムサリチレート
C-2:N-(ウンデカン-1-イルカルボニルオキシエチル)モルホリン
C-3:2,6-ジi-プロピルアニリン
C-4:トリn-ペンチルアミン
D-1:プロピレングリコールモノメチルエーテルアセテート
D-2:シクロヘキサノン
[A]重合体成分としての(A-1)100質量部、[B1]酸発生剤としての(B-9)10質量部、[B2]酸発生剤としての(B-1)7質量部、[C]酸拡散制御剤としての(C-1)5質量部並びに[D]溶媒としての(D-1)4,510質量部及び(D-2)1,930質量部を混合し、得られた混合物を20nmのメンブランフィルターでろ過し、感放射線性樹脂組成物(J-1)を調製した。
下記表2及び表3に示す種類及び含有量の各成分を用いた以外は、実施例1と同様に操作して、感放射線性樹脂組成物(J-2)~(J-29)及び(CJ-1)~(CJ-7)を調製した。表2及び表3中の「-」は、該当する成分を使用しなかったことを示す。
8インチのシリコンウェハ表面にスピンコーター(東京エレクトロン社の「CLEAN TRACK ACT8」)を使用して、上記調製した感放射線性樹脂組成物を塗工し、110℃で60秒間PBを行い、23℃で30秒間冷却して、平均厚み50nmのレジスト膜を形成した。次に、このレジスト膜に、簡易型の電子線描画装置(日立製作所社の「HL800D」、出力:50KeV、電流密度:5.0A/cm2)を用いて電子線を照射した。照射後、110℃で60秒間PEBを行った。それから、アルカリ現像液としての2.38質量%のTMAH水溶液を用いて23℃で60秒間現像し、水で洗浄し、乾燥してポジ型のレジストパターンを形成した。
上記形成したレジストパターンについて、下記測定を行うことにより、当該感放射線性樹脂組成物のLWR性能、CDU性能、解像性、断面形状の矩形性及び露光余裕度を評価した。評価結果を表4に示す。上記レジストパターンの測長には、走査型電子顕微鏡(日立ハイテクノロジーズ社の「S-9380」)を用いた。なお、上記レジストパターンの形成において、形成される線幅が100nm(L/S=1/1)となる露光量を最適露光量とした。
上記形成した線幅が100nm(L/S=1/1)のレジストパターンを、上記走査型電子顕微鏡を用い、パターン上部から観察した。線幅を任意のポイントで計50点測定し、その測定値の分布から3シグマ値を求め、これをLWR性能(nm)とした。LWR性能は、その値が小さいほど、線幅のばらつきが小さく良いことを示す。LWR性能は、20nm以下の場合は良好と、20nmを超える場合は不良と評価できる。
ホール径が100nm(H/S=1/1)であるレジストパターンを、上記走査型電子顕微鏡を用い、パターン上部から観察した。1,000nm×1,000nmの範囲でホール径を25点測定し、その平均値を任意のポイントで計50点測定し、その測定値の分布から3シグマ値を求め、これをCDU性能(nm)とした。CDU性能は、その値が小さいほど、長周期でのホール径のばらつきが小さく良いことを示す。CDU性能は、10nm以下の場合は良好と、10nmを超える場合は不良と評価できる。
上記最適露光量において解像される最小のレジストパターンの寸法を測定し、この測定値を解像性(nm)とした。解像性は、その値が小さいほど、より微細なパターンを形成でき良いことを示す。解像性は、形成される線幅が50nm以下の場合は良好と、50nmを超える場合は不良と評価できる。
上記最適露光量において解像されるレジストパターンの断面形状を観察し、レジストパターンの高さ方向の中間におけるホール径Lb及びレジストパターン上部におけるホール径Laを測定し、La/Lbの値を算出し、この値を断面形状の矩形性の指標とした。断面形状の矩形性は、0.9≦(La/Lb)≦1.1の場合は良好と、(La/Lb)≦0.9又は1.1≦(La/Lb)の場合は不良と評価できる。
上記最適露光量を含む露光量の範囲において、露光量を1μC/cm2ごとに変えて、それぞれレジストパターンを形成し、上記走査型電子顕微鏡を用いて、それぞれの線幅を測定した。得られた線幅と露光量の関係から、線幅が110nmとなる露光量E(110)と、線幅が90nmとなる露光量E(90)とを求め、露光余裕度=(E(110)-E(90))×100/(最適露光量)の式から露光余裕度(%)を算出した。露光余裕度は、その値が大きいほど、露光量が変動した際に得られるパターンの寸法の変動が小さく、デバイス作製時の歩留まりを高くすることができる。露光余裕度は、20%以上の場合は良好と、20%未満の場合は不良と評価できる。
Claims (12)
- 同一又は異なる重合体中に、第1構造単位、第2構造単位及び第3構造単位を有する重合体成分と、
第1感放射線性酸発生剤及び第2感放射線性酸発生剤を含む感放射線性酸発生剤成分と
を含有する感放射線性樹脂組成物であって、
上記第1構造単位が下記式(1)で表される基を含む構造単位、上記第2構造単位が芳香環に結合した水酸基を含む構造単位、上記第3構造単位が酸解離性基を含む構造単位であり、
上記第1感放射線性酸発生剤が、スルホ基に隣接する炭素原子を有しこの炭素原子にフッ素原子若しくは1価のフッ素化炭化水素基が結合するスルホン酸を発生し、上記第2感放射線性酸発生剤が、スルホ基に隣接する炭素原子とこの炭素原子に隣接する炭素原子とを有しこれらの炭素原子のいずれにもフッ素原子若しくは1価のフッ素化炭化水素基が結合していないスルホン酸、又はカルボキシ基に隣接する炭素原子を有しこの炭素原子にフッ素原子若しくは1価のフッ素化炭化水素基が結合するカルボン酸を発生する感放射線性樹脂組成物。
- 上記第1感放射線性酸発生剤から発生するスルホン酸が、下記式(3)で表される請求項1又は請求項2に記載の感放射線性樹脂組成物。
- 酸拡散制御剤をさらに含有する請求項1、請求項2又は請求項3に記載の感放射線性樹脂組成物。
- 上記重合体成分よりもフッ素原子の質量含有率が大きい重合体をさらに含有する請求項1から請求項4のいずれか1項に記載の感放射線性樹脂組成物。
- 上記重合体成分の含有量が、固形分換算で50質量%以上である請求項1から請求項5のいずれか1項に記載の感放射線性樹脂組成物。
- 上記重合体成分を構成する全構造単位に対する上記第2構造単位の含有割合が、20モル%以上70モル%以下である請求項1から請求項6のいずれか1項に記載の感放射線性樹脂組成物。
- 上記重合体成分を構成する全構造単位に対する上記第1構造単位の含有割合が、5モル%以上50モル%以下である請求項1から請求項7のいずれか1項に記載の感放射線性樹脂組成物。
- 上記感放射線性酸発生剤成分全体に対する上記第1感放射線性酸発生剤及び第2感放射線性酸発生剤の合計含有量が、70質量%以上である請求項1から請求項8のいずれか1項に記載の感放射線性樹脂組成物。
- 上記感放射線性酸発生剤成分全体に対する上記第1感放射線性酸発生剤の含有量が、10質量%以上である請求項1から請求項9のいずれか1項に記載の感放射線性樹脂組成物。
- 基板の一方の面に、請求項1から請求項10のいずれか1項に記載の感放射線性樹脂組成物を塗工する工程と、
上記塗工工程により得られるレジスト膜を露光する工程と、
上記露光されたレジスト膜を現像する工程と
を備えるレジストパターン形成方法。 - 上記露光工程で用いる放射線が、極端紫外線又は電子線である請求項11に記載のレジストパターン形成方法。
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190371600A1 (en) * | 2018-05-31 | 2019-12-05 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photosensitive Groups in Resist Layer |
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WO2021200056A1 (ja) * | 2020-03-30 | 2021-10-07 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、パターン形成方法、電子デバイスの製造方法、フォトマスク製造用感活性光線性又は感放射線性樹脂組成物、及びフォトマスクの製造方法 |
US20210318613A9 (en) * | 2019-06-14 | 2021-10-14 | Jsr Corporation | Radiation-sensitive resin composition and resist pattern-forming method |
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JP7441930B2 (ja) | 2021-12-30 | 2024-03-01 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシー | フォトレジスト組成物及びパターン形成方法 |
JP7478540B2 (ja) | 2019-01-22 | 2024-05-07 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN112764313A (zh) * | 2021-01-22 | 2021-05-07 | 宁波南大光电材料有限公司 | 一种光刻胶组合物及其制备方法 |
CN112925166A (zh) * | 2021-01-22 | 2021-06-08 | 宁波南大光电材料有限公司 | 一种高分辨率光刻胶 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007304537A (ja) * | 2005-07-26 | 2007-11-22 | Fujifilm Corp | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
JP2008304590A (ja) * | 2007-06-06 | 2008-12-18 | Shin Etsu Chem Co Ltd | フォトマスクブランク、レジストパターンの形成方法、及びフォトマスクの製造方法 |
JP2011008237A (ja) * | 2009-05-26 | 2011-01-13 | Shin-Etsu Chemical Co Ltd | レジスト材料及びパターン形成方法 |
JP2012073606A (ja) * | 2010-09-03 | 2012-04-12 | Shin Etsu Chem Co Ltd | パターン形成方法及び化学増幅ポジ型レジスト材料 |
JP2016085382A (ja) * | 2014-10-27 | 2016-05-19 | Jsr株式会社 | レジストパターン形成方法及び感放射線性樹脂組成物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3972438B2 (ja) | 1998-01-26 | 2007-09-05 | 住友化学株式会社 | 化学増幅型のポジ型レジスト組成物 |
JP2003005375A (ja) | 2001-06-21 | 2003-01-08 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
JP4832237B2 (ja) | 2006-09-27 | 2011-12-07 | 富士フイルム株式会社 | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
-
2017
- 2017-10-04 KR KR1020197009792A patent/KR102447850B1/ko active IP Right Grant
- 2017-10-04 JP JP2018544977A patent/JP7041359B2/ja active Active
- 2017-10-04 WO PCT/JP2017/036196 patent/WO2018070327A1/ja active Application Filing
-
2019
- 2019-04-12 US US16/382,353 patent/US20190243244A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007304537A (ja) * | 2005-07-26 | 2007-11-22 | Fujifilm Corp | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
JP2008304590A (ja) * | 2007-06-06 | 2008-12-18 | Shin Etsu Chem Co Ltd | フォトマスクブランク、レジストパターンの形成方法、及びフォトマスクの製造方法 |
JP2011008237A (ja) * | 2009-05-26 | 2011-01-13 | Shin-Etsu Chemical Co Ltd | レジスト材料及びパターン形成方法 |
JP2012073606A (ja) * | 2010-09-03 | 2012-04-12 | Shin Etsu Chem Co Ltd | パターン形成方法及び化学増幅ポジ型レジスト材料 |
JP2016085382A (ja) * | 2014-10-27 | 2016-05-19 | Jsr株式会社 | レジストパターン形成方法及び感放射線性樹脂組成物 |
Cited By (34)
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---|---|---|---|---|
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JP7304999B2 (ja) | 2018-06-28 | 2023-07-07 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
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US11834419B2 (en) | 2018-10-11 | 2023-12-05 | Lg Chem, Ltd. | Compound, photoresist composition comprising same, photoresist pattern comprising same, and method for manufacturing photoresist pattern |
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KR20190067169A (ko) | 2019-06-14 |
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