WO2024147288A1 - パターン形成方法、パターン形成用キット、及び電子デバイスの製造方法 - Google Patents

パターン形成方法、パターン形成用キット、及び電子デバイスの製造方法 Download PDF

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WO2024147288A1
WO2024147288A1 PCT/JP2023/045793 JP2023045793W WO2024147288A1 WO 2024147288 A1 WO2024147288 A1 WO 2024147288A1 JP 2023045793 W JP2023045793 W JP 2023045793W WO 2024147288 A1 WO2024147288 A1 WO 2024147288A1
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group
composition
resin
compound
developer
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English (en)
French (fr)
Japanese (ja)
Inventor
英幸 石原
佑真 楜澤
光宏 藤田
智美 高橋
敏明 福原
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Fujifilm Corp
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Fujifilm Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor

Definitions

  • Mn E is the number average molecular weight of the resin (E).
  • ⁇ Mn E is the change in Mn E.
  • DR is the dissolution rate (nm/s) of the resist film formed using the composition (A) in the developer (J).
  • log 10 DR is the common logarithm of DR.
  • ⁇ log 10 DR is the amount of change in log 10 DR.
  • [P] is the content (mol %) of the compound (P) relative to the total solid content in the composition (A), and ⁇ [P] is the change in [P].
  • a kit for pattern formation comprising: a composition (A) containing a resin (E) whose main chain is decomposed by irradiation with actinic rays or radiation and a compound (P) that is decomposed by irradiation with actinic rays or radiation; and a developer (J), a dissolution rate of a resist film formed using the composition (A) in the developer (J) is 0.05 nm/s or less;
  • a kit for pattern formation wherein b/a, which is a value obtained by dividing b defined in the following formula (f2) by a defined in the following formula (f1), satisfies 10,000 ⁇ b/a ⁇ 30,000.
  • Mn E is the number average molecular weight of the resin (E).
  • ⁇ Mn E is the change in Mn E.
  • DR is the dissolution rate (nm/s) of the resist film formed using the composition (A) in the developer (J).
  • log 10 DR is the common logarithm of DR.
  • ⁇ log 10 DR is the amount of change in log 10 DR.
  • [P] is the content (mol %) of the compound (P) relative to the total solid content in the composition (A), and ⁇ [P] is the change in [P].
  • the present invention provides a pattern formation method, a pattern formation kit, and a method for manufacturing an electronic device that includes the pattern formation method, all of which have excellent LWR performance and resolution.
  • 1 is a graph showing the relationship between a and b in the examples and the comparative examples.
  • the present invention will be described in detail below. The following description of the components may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment.
  • the notation of groups (atomic groups) that does not indicate whether they are substituted or unsubstituted includes both unsubstituted and substituted groups, unless it is contrary to the spirit of the present invention.
  • alkyl group includes not only alkyl groups that do not have a substituent (unsubstituted alkyl groups), but also alkyl groups that have a substituent (substituted alkyl groups).
  • organic group in the present specification refers to a group that contains at least one carbon atom.
  • exposure includes not only exposure to the emission line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light, X-rays, EUV light, and the like, but also drawing with particle beams such as electron beams and ion beams.
  • the word “to” is used to mean that the numerical values before and after it are included as the lower limit and upper limit.
  • the bonding direction of the divalent group described in this specification is not limited unless otherwise specified. For example, when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-. In addition, the above compound may be "X-CO-O-Z" or "X-O-CO-Z".
  • pKa can also be obtained by molecular orbital calculation.
  • a specific example of this method is a method of calculating H + dissociation free energy in an aqueous solution based on a thermodynamic cycle.
  • the H + dissociation free energy can be calculated, for example, by DFT (density functional theory), but various other methods have been reported in literature, and the calculation method is not limited to this.
  • DFT density functional theory
  • Gaussian16 is an example.
  • resin (E1) is prepared by changing the number average molecular weight from the reference value (Mn E0) by +20% (i.e., 1.2 ⁇ Mn E0 ) and resin (E2) is prepared by changing the number average molecular weight from the reference value (Mn E0 ) by -20% (i.e., 0.8 ⁇ Mn E0 ) without changing the constituent components (types of repeating units contained in resin (E0)) and the constituent ratio (content of each repeating unit contained in resin ( E0 )) of resin (E0).
  • the value of a can be adjusted, for example, by adjusting the polarity of the resin (E) (the polarity of the monomer used) or by adjusting the glass transition temperature (Tg) of the resin (E).
  • the polarity of the resin (E) is increased, the value of a tends to be increased.
  • a method of introducing a polar group can be used.
  • the polar group include an ether group, an ester group, a carbonyl group, and a group containing at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom, such as a specific functional group described below.
  • composition (A) (also referred to as “composition (A P1 )" is prepared in which the content of compound (P) is increased by +20% from the reference value (W P0 ) (i.e., 1.2 x W P0 ), and a composition (A) (also referred to as “composition (A P2 )”) is prepared in which the content of compound (P) is decreased by -20% from the reference value (W P0 ) (i.e., 0.8 x W P0 ).
  • the dissolution rates (units: nm/s) of each resist film formed using composition (A P0 ), composition (A P1 ), and composition (A P2 ) in developer (J) are measured, DR P0 , DR P1 , and DR P2 .
  • a graph is prepared with the content of compound (P) on the horizontal axis and the dissolution rate of the resist film in developer (J) on the vertical axis, and b is calculated from the slope of a straight line prepared using the least squares method from the data for the three points.
  • the top coat also preferably contains a compound containing at least one group or bond selected from the group consisting of an ether bond, a thioether bond, a hydroxyl group, a thiol group, a carbonyl bond, and an ester bond.
  • ester-based solvents include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, pentyl acetate, isopentyl acetate, amyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl-3-ethoxypropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl formate, ethyl formate, butyl formate, propyl formate, ethyl lactate, butyl lactate, propyl lactate, butyl butanoate, methyl 2-hydroxyisobutyrate, isoamyl acetate, isobutyl isobutyrate, and butyl propionate.
  • the pattern forming method may include, after step 3, a step of cleaning with a rinsing liquid.
  • the method of the rinsing step is not particularly limited, and examples thereof include a method of continuously discharging a rinsing liquid onto a substrate rotating at a constant speed (spin coating method), a method of immersing a substrate in a tank filled with the rinsing liquid for a certain period of time (dip method), and a method of spraying the rinsing liquid onto the substrate surface (spray method).
  • the pattern forming method of the present invention may also include a heating step (Post Bake) after the rinsing step. This step removes the developer (J) and rinsing solution remaining between the patterns and inside the pattern due to baking. This step also has the effect of annealing the resist pattern and improving the surface roughness of the pattern.
  • the heating step after the rinsing step is usually performed at 40 to 250° C. (preferably 90 to 200° C.) for usually 10 seconds to 3 minutes (preferably 30 seconds to 120 seconds).
  • the composition (A) contains a resin (E) whose main chain is decomposed when irradiated with actinic rays or radiation.
  • the resin (E) is a resin whose main chain is decomposed when irradiated with actinic rays or radiation, and is preferably a resin whose main chain is decomposed when irradiated with X-rays, electron beams or extreme ultraviolet rays.
  • the resin (E) preferably contains a repeating unit represented by the following formula (1).
  • X represents a halogen atom, a fluorinated alkyl group, or a fluorinated cycloalkyl group.
  • Ra represents a hydrogen atom or a substituent.
  • R 1 represents a substituent. R 1 and Ra may be bonded to each other to form a ring.
  • the substituent is not particularly limited, but examples thereof include a halogen atom (preferably a fluorine atom or an iodine atom) and a specific functional group described later.
  • Ra is preferably a hydrogen atom in that the effects of the present invention are more excellent.
  • R X represents a hydrogen atom or an organic group.
  • the organic group represented by R 1 X is not particularly limited, but is preferably, for example, a linear or branched alkyl group or a cycloalkyl group.
  • the alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 6 carbon atoms, and further preferably has 1 to 3 carbon atoms.
  • the cycloalkyl group may be either monocyclic or polycyclic.
  • the aryl group may be either a monocyclic or polycyclic ring, and is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 15 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms.
  • the aryl group is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group.
  • the aryl group may have a substituent.
  • the repeating unit represented by formula (1) is preferably a repeating unit represented by the following formula (1A), in that the effect of the present invention is more excellent.
  • X and Ra have the same meanings as X and Ra in formula (1), and preferred embodiments are also the same.
  • L 2A represents -O- or -N(R x )-.
  • R x represents a hydrogen atom or an organic group. Examples of the organic group represented by R x include the same as R x in formula (1-1) above.
  • R 1A represents a hydrogen atom or an organic group. Examples of the organic group represented by R 1A include the same as R 1A in formula (1-1) above.
  • Ra and R 1A may be bonded to each other to form a ring. Examples of the ring formed by Ra and R 1A bonded to each other include the same rings as those formed by Ra and R 1 in the above formula (1) bonded to each other.
  • Resin (E) may contain a repeating unit represented by the following formula (2):
  • A1 represents a hydrogen atom, an alkyl group or a cycloalkyl group.
  • Rb represents a hydrogen atom or a substituent.
  • Ar represents an aromatic hydrocarbon group. Ar and Rb may be bonded to each other to form a ring.
  • the onium salt structure is a structural moiety having an ion pair of a cation and an anion, and is preferably a structural moiety represented by “X n ⁇ nM + ” (wherein n represents, for example, an integer of 1 to 3, and preferably represents 1 or 2).
  • M + represents a structural moiety containing a positively charged atom or atomic group
  • Xn- represents a structural moiety containing a negatively charged atom or atomic group.
  • the resin (E) preferably contains one or more functional groups (specific functional groups) selected from the group consisting of hydroxyl groups (alcoholic hydroxyl groups and phenolic hydroxyl groups), carboxyl groups, amino groups, amide groups, imide groups, thiol groups, acetyl groups, sulfonic acid groups, sulfonamide groups, and acetoxy groups, and more preferably contains one or more functional groups selected from the group consisting of phenolic hydroxyl groups and carboxyl groups.
  • functional groups specific functional groups
  • the case where the salt structure moiety is a part of the photodecomposable onium salt compound corresponds to, for example, a structure in which two or more salt structure moieties are linked together, such as the photodecomposable onium salt PG2 described later.
  • the number of salt structure moieties in the photodecomposable onium salt is not particularly limited, but is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3.
  • the organic acid generated by decomposition of the photodecomposable onium salt compound by exposure is a polyvalent acid having two or more acid groups.
  • one of R 201 to R 203 may be an aryl group, and the remaining two of R 201 to R 203 may be bonded to form a ring structure, which may contain an oxygen atom, a sulfur atom, an ester group, an amide group, or a carbonyl group in the ring.
  • Examples of the group formed by bonding two of R 201 to R 203 include alkylene groups in which one or more methylene groups may be substituted with oxygen atoms, sulfur atoms, ester groups, amide groups, and/or carbonyl groups (e.g., butylene group, pentylene group, or -CH 2 -CH 2 -O-CH 2 -CH 2 -).
  • Each of R 201 to R 203 independently represents preferably an alkyl group, a cycloalkyl group, an allyl group, or a vinyl group, more preferably a linear or branched 2-oxoalkyl group, a 2-oxocycloalkyl group, or an alkoxycarbonylmethyl group, and still more preferably a linear or branched 2-oxoalkyl group.
  • the cation (ZaI-3b) is a cation represented by the following formula (ZaI-3b).
  • R 6c and R 7c each independently represent a hydrogen atom, an alkyl group (such as a t-butyl group), a cycloalkyl group, a halogen atom, a cyano group, or an aryl group.
  • R x and R y each independently represent an alkyl group, a cycloalkyl group, a 2-oxoalkyl group, a 2-oxocycloalkyl group, an alkoxycarbonylalkyl group, an allyl group, or a vinyl group.
  • R 1c to R 5c , R 5c and R 6c , R 6c and R 7c , R 5c and R x , and R x and R y may be bonded to each other to form a ring, and each of these rings may independently contain an oxygen atom, a sulfur atom, a ketone group, an ester bond, or an amide bond.
  • the ring include an aromatic or non-aromatic hydrocarbon ring, an aromatic or non-aromatic heterocycle, and a polycyclic condensed ring formed by combining two or more of these rings.
  • the ring include a 3- to 10-membered ring, preferably a 4- to 8-membered ring, and more preferably a 5- or 6-membered ring.
  • the group formed by combining any two or more of R 1c to R 5c , R 6c and R 7c , and R x and R y includes alkylene groups such as butylene and pentylene, in which the methylene group may be substituted with a heteroatom such as an oxygen atom.
  • the groups formed by combining R5c and R6c , and R5c and Rx are preferably a single bond or an alkylene group. Examples of the alkylene group include a methylene group and an ethylene group.
  • R 1c to R 5c , R 6c , R 7c , R x , R y , and any two or more of R 1c to R 5c , R 5c and R 6c , R 6c and R 7c , R 5c and R x , and R x and R y may each have a substituent.
  • the cation (ZaI-4b) is a cation represented by the following formula (ZaI-4b).
  • l represents an integer of 0 to 2.
  • r represents an integer of 0 to 8.
  • R 13 represents a hydrogen atom, a halogen atom (e.g., a fluorine atom, an iodine atom, etc.), a hydroxyl group, an alkyl group, a halogenated alkyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or a group having a cycloalkyl group (which may be a cycloalkyl group itself or a group containing a cycloalkyl group as a part). These groups may have a substituent.
  • a halogen atom e.g., a fluorine atom, an iodine atom, etc.
  • R 13 represents a hydrogen atom, a halogen atom (e.g., a fluorine atom, an iodine atom, etc.), a hydroxyl group,
  • R 14 represents a hydroxyl group, a halogen atom (e.g., a fluorine atom, an iodine atom, etc.), an alkyl group, a halogenated alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylsulfonyl group, a cycloalkylsulfonyl group, or a group having a cycloalkyl group (may be a cycloalkyl group itself or a group containing a cycloalkyl group as a part). These groups may have a substituent.
  • a halogen atom e.g., a fluorine atom, an iodine atom, etc.
  • each independently represents the above group such as a hydroxyl group.
  • Each R 15 independently represents an alkyl group, a cycloalkyl group, or a naphthyl group. Two R 15 may be bonded to each other to form a ring. When two R 15 are bonded to each other to form a ring, the ring skeleton may contain a heteroatom such as an oxygen atom or a nitrogen atom. In one embodiment, it is preferable that two R 15 are alkylene groups and are bonded to each other to form a ring structure.
  • the alkyl group, the cycloalkyl group, and the naphthyl group, as well as the ring formed by bonding two R 15 to each other may have a substituent.
  • R 204 and R 205 each independently represent an aryl group, an alkyl group or a cycloalkyl group.
  • the aryl group of R 204 and R 205 preferably has 2 to 20 carbon atoms, more preferably a phenyl group or naphthyl group, and particularly preferably a phenyl group.
  • the aryl group of R 204 and R 205 may be an aryl group having a heterocycle containing an oxygen atom, a nitrogen atom, a sulfur atom, or the like.
  • Examples of the skeleton of the aryl group having a heterocycle include pyrrole, furan, thiophene, indole, benzofuran, and benzothiophene.
  • the alkyl group and cycloalkyl group of R 204 and R 205 are preferably a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, or a pentyl group), or a cycloalkyl group having 3 to 10 carbon atoms (e.g., a cyclopentyl group, a cyclohexyl group, or a norbornyl group).
  • the organic anion represented by X 2 - in the photodecomposable onium salt compound PG1 is preferably a non-nucleophilic anion (an anion having an extremely low ability to cause a nucleophilic reaction).
  • non-nucleophilic anions include sulfonate anions (aliphatic sulfonate anions, aromatic sulfonate anions, camphorsulfonate anions, etc.), carboxylate anions (aliphatic carboxylate anions, aromatic carboxylate anions, aralkyl carboxylate anions, etc.), sulfonylimide anions, bis(alkylsulfonyl)imide anions, and tris(alkylsulfonyl)methide anions.
  • the organic anion is preferably, for example, an organic anion represented by the following formula (DA):
  • a 31 - represents an anionic group.
  • R a1 represents a hydrogen atom or a monovalent organic group.
  • L a1 represents a single bond or a divalent linking group.
  • a 31 - and R a1 may be bonded to each other to form a ring.
  • a 31 - represents an anionic group.
  • the anionic group represented by A 31 - is not particularly limited, but is preferably a group selected from the group consisting of groups represented by formulae (BA-1) to (BA-14), and more preferably formulae (BA-1), (BA-2), (BA-3), (BA-4), (BA-5), (BA-6), (BA-10), (BA-12), (BA-13), and (BA-14).
  • R 1 X1 each independently represents a monovalent organic group.
  • each R X2 independently represents a hydrogen atom or a substituent other than a fluorine atom or a perfluoroalkyl group.
  • Two R X2 in formula (BA-7) may be the same or different.
  • R XF1 represents a hydrogen atom, a fluorine atom, or a perfluoroalkyl group. Of the two R XF1 , at least one represents a fluorine atom or a perfluoroalkyl group.
  • R XF1 in formula (BA-8) may be the same or different.
  • R X3 represents a hydrogen atom, a halogen atom, or a monovalent organic group.
  • n1 represents an integer of 0 to 4.
  • R 2 XF2 represents a fluorine atom or a perfluoroalkyl group.
  • the bond to the bonding position represented by * in formula (BA-14) is preferably a phenylene group which may have a substituent. Examples of the substituent which the phenylene group may have include a halogen atom.
  • R 1 X1 each independently represents a monovalent organic group.
  • R X1 is preferably an alkyl group (which may be linear or branched, and preferably has 1 to 15 carbon atoms), a cycloalkyl group (which may be monocyclic or polycyclic, and preferably has 3 to 20 carbon atoms), or an aryl group (which may be monocyclic or polycyclic, and preferably has 6 to 20 carbon atoms).
  • the above group represented by R X1 may have a substituent.
  • the atom in R X1 in formula (BA-5) which is directly bonded to N- is neither a carbon atom in --CO-- nor a sulfur atom in --SO 2 --.
  • the cycloalkyl group in R X1 may be a monocyclic or polycyclic group.
  • Examples of the cycloalkyl group in R X1 include a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group.
  • the substituent that the cycloalkyl group in R X1 may have is not particularly limited, but is preferably an alkyl group (which may be linear or branched, and preferably has 1 to 5 carbon atoms). One or more of the carbon atoms that are ring members of the cycloalkyl group in R X1 may be replaced with a carbonyl carbon atom.
  • the alkyl group in R 3 X1 preferably has 1 to 10 carbon atoms, and more preferably has 1 to 5 carbon atoms.
  • the substituent that the alkyl group in R may have is not particularly limited, but is preferably, for example, a cycloalkyl group, a fluorine atom, or a cyano group. Examples of the cycloalkyl group as the substituent are the same as those described when R is a cycloalkyl group.
  • the alkyl group in R X1 has a fluorine atom as the above-mentioned substituent, the above-mentioned alkyl group may be a perfluoroalkyl group.
  • the alkyl group in R X1 may have one or more -CH 2 - substituted with a carbonyl group.
  • the aryl group in R X1 is, for example, preferably a phenyl group or a naphthyl group, and more preferably a phenyl group.
  • the substituent that the aryl group in R may have is not particularly limited, but is preferably an alkyl group, a fluorine atom, or a cyano group. Examples of the alkyl group as the substituent are the same as those described in the case where R is an alkyl group.
  • each R X2 independently represents a hydrogen atom or a substituent other than a fluorine atom or a perfluoroalkyl group (for example, an alkyl group not containing a fluorine atom and a cycloalkyl group not containing a fluorine atom).
  • the two R X2 in formula (BA-7) may be the same or different.
  • R XF1 represents a hydrogen atom, a fluorine atom, or a perfluoroalkyl group. However, among the multiple R XF1 , at least one represents a fluorine atom or a perfluoroalkyl group.
  • the two R XF1 in formula (BA-8) may be the same or different.
  • the number of carbon atoms of the perfluoroalkyl group represented by R XF1 is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 6.
  • R X3 represents a hydrogen atom, a halogen atom, or a monovalent organic group.
  • the halogen atom represented by R X3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
  • the monovalent organic group represented by R 1 X3 is the same as the monovalent organic group described as R 1 X1 .
  • n1 represents an integer of 0 to 4.
  • n1 is preferably an integer of 0 to 2, and more preferably 0 or 1. When n1 represents an integer of 2 to 4, multiple R 3 X3 may be the same or different.
  • R 2 XF2 represents a fluorine atom or a perfluoroalkyl group.
  • the perfluoroalkyl group represented by R 2 XF2 preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
  • the number of carbon atoms of the monovalent organic group of R a1 is not particularly limited, but preferably is 1 to 30 carbon atoms, and more preferably is 1 to 20 carbon atoms.
  • R a1 is preferably an alkyl group, a cycloalkyl group or an aryl group.
  • the alkyl group may be linear or branched, and is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, and even more preferably an alkyl group having 1 to 10 carbon atoms.
  • the cycloalkyl group may be monocyclic or polycyclic, and is preferably a cycloalkyl group having 3 to 20 carbon atoms, more preferably a cycloalkyl group having 3 to 15 carbon atoms, and even more preferably a cycloalkyl group having 3 to 10 carbon atoms.
  • the aryl group may be monocyclic or polycyclic, and is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 15 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms.
  • the cycloalkyl group may contain heteroatoms as ring members.
  • the heteroatom is not particularly limited, but examples thereof include a nitrogen atom and an oxygen atom.
  • the alkyl group, cycloalkyl group and aryl group may further have a substituent.
  • a 31 - and R a1 may be bonded to each other to form a ring.
  • the divalent linking group represented by L a1 is not particularly limited, and examples thereof include an alkylene group, a cycloalkylene group, an aromatic group, -O-, -CO-, -COO-, and a group formed by combining two or more of these.
  • the alkylene group may be linear or branched and preferably has 1 to 20 carbon atoms, and more preferably has 1 to 10 carbon atoms.
  • the cycloalkylene group may be monocyclic or polycyclic and preferably has 3 to 20 carbon atoms, and more preferably has 3 to 10 carbon atoms.
  • the aromatic group is a divalent aromatic group, preferably an aromatic group having 6 to 20 carbon atoms, and more preferably an aromatic group having 6 to 15 carbon atoms.
  • the aromatic ring constituting the aromatic group may be an aromatic hydrocarbon ring or an aromatic heterocycle.
  • the aromatic ring is not particularly limited, but may be, for example, an aromatic ring having 6 to 20 carbon atoms, specifically, a benzene ring, a naphthalene ring, an anthracene ring, a thiophene ring, etc.
  • the aromatic ring constituting the aromatic group is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
  • the alkylene group, cycloalkylene group and aromatic group may further have a substituent, and the substituent is preferably a halogen atom.
  • L a1 preferably represents a single bond.
  • the photodecomposable onium salt compound PG1 it is also preferable to use, for example, the photoacid generators disclosed in paragraphs [0135] to [0171] of WO 2018/193954, paragraphs [0077] to [0116] of WO 2020/066824, and paragraphs [0018] to [0075] and [0334] to [0335] of WO 2017/154345.
  • the molecular weight of the photodegradable onium salt compound PG1 is preferably 3000 or less, more preferably 2000 or less, and even more preferably 1000 or less.
  • the molecular weight of the photodegradable onium salt compound PG1 is preferably 100 or more.
  • Photodecomposable onium salt compound PG2 Another example of a suitable embodiment of the photodecomposable onium salt compound includes the following compound (I) and compound (II) (hereinafter, "compound (I) and compound (II)” are also referred to as “photodecomposable onium salt compound PG2").
  • the photodecomposable onium salt compound PG2 has two or more of the above-mentioned salt structural moieties and is a compound that generates a polyvalent organic acid upon exposure to light.
  • the photodecomposable onium salt compound PG2 will now be described.
  • Compound (I) is a compound having one or more structural moieties X and one or more structural moieties Y, which generates an acid containing a first acidic moiety derived from the structural moiety X and a second acidic moiety derived from the structural moiety Y when irradiated with actinic rays or radiation:
  • Structural moiety X a structural moiety consisting of an anionic moiety A 1 - and a cationic moiety M 1 + , and which forms a first acidic moiety represented by HA 1 upon exposure to actinic rays or radiation.
  • Structural moiety Y a structural moiety consisting of an anionic moiety A 2 - and a cationic moiety M 2 + , and which forms a second acidic moiety represented by HA 2 upon exposure to actinic rays or radiation.
  • compound (I) satisfies the following condition I.
  • Compound PI which is obtained by replacing the cationic moiety M 1 + in the structural moiety X and the cationic moiety M 2 + in the structural moiety Y in compound (I) with H + , has an acid dissociation constant a1 derived from the acidic moiety represented by HA 1 , which is obtained by replacing the cationic moiety M 1 + in the structural moiety X with H + , and an acid dissociation constant a2 derived from the acidic moiety represented by HA 2 , which is obtained by replacing the cationic moiety M 2 + in the structural moiety Y with H + , and the acid dissociation constant a2 is greater than the acid dissociation constant a1.
  • the compound PI corresponds to an acid generated when compound (I) is irradiated with actinic rays or radiation.
  • the structural moieties X may be the same or different from each other.
  • the two or more A 1 ⁇ and the two or more M 1 + may be the same or different from each other.
  • the A 1 - and A 2 - , and the M 1 + and M 2 + may be the same or different, but it is preferable that the A 1 - and A 2 - are different.
  • the anionic moiety A 1 - and the anionic moiety A 2 - are structural moieties containing a negatively charged atom or atomic group, and examples thereof include structural moieties selected from the group consisting of the following formulae (AA-1) to (AA-3) and (BB-1) to (BB-6). In the following formulae (AA-1) to (AA-3) and (BB-1) to (BB-6), * represents a bonding position.
  • R A represents a monovalent organic group. Examples of the monovalent organic group represented by R A include a cyano group, a trifluoromethyl group, and a methanesulfonyl group.
  • the compound (II) can generate a compound PII (acid) having an acidic site represented by HA 1 in which the cationic site M 1 + in the structural site X is replaced with H + .
  • the compound PII represents a compound having the acidic site represented by HA 1 and a structural site Z which is a nonionic site capable of neutralizing an acid.
  • the definition of the structural moiety X and the definitions of A 1 - and M 1 + in compound (II) are the same as the definition of the structural moiety X and the definitions of A 1 - and M 1 + in compound (I) described above, and the preferred embodiments are also the same.
  • the two or more structural moieties X may be the same or different from each other, and the two or more A 1 ⁇ and the two or more M 1 + may be the same or different from each other.
  • composition (A) When such a solvent is used in combination with resin (E), the coatability of composition (A) is improved and patterns with fewer development defects are easily formed. This is presumably because these solvents have an excellent balance of solubility, boiling point, and viscosity for resin (E), which makes it possible to suppress unevenness in the film thickness of the resist film, which is a film formed from composition (A), and the occurrence of precipitates during spin coating.
  • the content of the solvent in composition (A) is preferably determined so that the solids concentration is 0.5 to 30 mass %, and more preferably 1 to 20 mass %, in order to provide better coatability.
  • composition (A) and various materials used in the pattern formation method of the present invention preferably do not contain impurities such as metals.
  • the content of impurities contained in these materials is preferably 1 mass ppm (parts per million) or less, more preferably 10 mass ppb (parts per billion) or less, even more preferably 100 mass ppt (parts per trillion) or less, particularly preferably 10 mass ppt or less, and most preferably 1 mass ppt or less.
  • examples of metal impurities include Na, K, Ca, Fe, Cu, Mg, Al, Li, Cr, Ni, Sn, Ag, As, Au, Ba, Cd, Co, Pb, Ti, V, W, and Zn.
  • the present invention also relates to a kit for pattern formation.
  • the kit for pattern formation of the present invention is a kit for pattern formation comprising: a composition (A) containing a resin (E) whose main chain is decomposed by irradiation with actinic rays or radiation and a compound (P) that is decomposed by irradiation with actinic rays or radiation; and a developer (J), a dissolution rate of a resist film formed using the composition (A) in the developer (J) is 0.05 nm/s or less;
  • b/a which is a value obtained by dividing b defined in the following formula (f2) by a defined in the following formula (f1), satisfies 10,000 ⁇ b/a ⁇ 30,000.
  • An underlayer film-forming composition AL412 (manufactured by Brewer Science) was applied onto a silicon wafer and baked at 205° C. for 60 seconds to form an underlayer film having a thickness of 20 nm.
  • a composition (A) (resist composition) shown in Tables 1 and 2 was applied onto the underlayer film and baked at 100° C. for 60 seconds to form a resist film having a thickness of 30 nm.
  • the silicon wafer having the resist film thus obtained was subjected to pattern irradiation using an EUV exposure apparatus (Exitech, Micro Exposure Tool, NA 0.3, Quadrupol, outer sigma 0.68, inner sigma 0.36).
  • a mask with a line size of 20 nm and a line:space ratio of 1:1 was used as a reticle.
  • the exposed resist film was baked at 100° C. for 60 seconds, and then developed with n-butyl acetate (nBA), which is a developer (J), by puddling for 30 seconds.
  • nBA n-butyl acetate
  • J developer
  • the wafer was then rotated at 4000 rpm for 30 seconds to obtain a line and space pattern with a line size of 20 nm and a line:space ratio of 1:1.
  • n-butyl acetate (nBA) was used as the developer (J), and a and b were determined by the above-mentioned method, and b/a was calculated.
  • the reference value (Mn E0 ) of the number average molecular weight of the resin (E) when determining a was the value of "Mn” shown in Tables 1 and 2.
  • the reference value (W P0 ) of the content of compound (P) when determining b was the value obtained by converting the "content (mass %)" of compound (P) shown in Tables 1 and 2 into "mol %".
  • Examples 2-1 to 2-9, Comparative Examples 2-1 to 2-6: EUV Exposure A composition (A) (resist composition) was prepared in the same manner as in Example 1-1, etc. described above, except that the components and solvents shown in Table 3 were used.
  • the unit of the dissolution rate (Rmin) is "nm/s”.
  • the resolution and LWR performance were evaluated in the same manner as in Example 1-1, except that a developer (J) containing nBA and isoamyl acetate in a mass ratio of 5:5 was used. The results are shown in Table 3.
  • Examples 3-1 to 3-4 EUV exposure
  • a composition (A) resist composition
  • Example 1-1 resist composition
  • Example 1-1 resist composition
  • Example 1-1 developer composition
  • Example 1-1 developer composition
  • Table 4 developer composition
  • the developer (J) shown in Table 4 was used to determine b/a and the dissolution rate (Rmin) of the resist film in the developer (J).
  • the unit of the dissolution rate (Rmin) is "nm/s”.
  • the resolution and LWR performance were evaluated in the same manner as in Example 1-1, etc., except that the developer (J) shown in Table 4 was used as the developer (J).
  • the results are shown in Table 4.
  • FIG. 1 shows a graph with the value of a on the horizontal axis and the value of b on the vertical axis.
  • the present invention provides a pattern formation method, a pattern formation kit, and a method for manufacturing an electronic device that includes the pattern formation method, all of which have excellent LWR performance and resolution.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Materials For Photolithography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
PCT/JP2023/045793 2023-01-06 2023-12-20 パターン形成方法、パターン形成用キット、及び電子デバイスの製造方法 Ceased WO2024147288A1 (ja)

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Publication number Priority date Publication date Assignee Title
WO2020137935A1 (ja) * 2018-12-27 2020-07-02 三菱瓦斯化学株式会社 化合物、（共）重合体、組成物、パターン形成方法、及び化合物の製造方法
WO2021153466A1 (ja) * 2020-01-31 2021-08-05 富士フイルム株式会社 ポジ型レジスト組成物、レジスト膜、パターン形成方法、及び電子デバイスの製造方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020137935A1 (ja) * 2018-12-27 2020-07-02 三菱瓦斯化学株式会社 化合物、（共）重合体、組成物、パターン形成方法、及び化合物の製造方法
WO2021153466A1 (ja) * 2020-01-31 2021-08-05 富士フイルム株式会社 ポジ型レジスト組成物、レジスト膜、パターン形成方法、及び電子デバイスの製造方法

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