Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/10—Esters
• • 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
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
  • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
• • 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
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
  • G03F7/031—Organic compounds not covered by group G03F7/029
• • 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

Definitions

• the present invention relates to an actinic ray- or radiation-sensitive resin composition, a resist film, a pattern forming method, and a method for manufacturing an electronic device.
• the exposed portion is removed to obtain a desired pattern.
• the wavelength of the exposure light source has become shorter and the numerical aperture (NA) of the projection lens has become higher, and currently, an exposure machine using an ArF excimer laser having a wavelength of 193 nm as a light source has been developed.
• pattern formation methods using extreme ultraviolet (EUV) and electron beam (EB) as light sources are also being considered in recent years. Under these circumstances, various compositions have been proposed as actinic ray-sensitive or radiation-sensitive resin compositions.
• Y 0 and L 0 respectively have the same meanings as Y 0 and L 0 in the above formula (U-1).
• X represents a halogen atom, a fluorinated alkyl group or a fluorinated cycloalkyl group.
• Ra represents a hydrogen atom or a substituent.
• L 1 represents -CO-, -SO- or -SO 2 -.
• Z 1 represents -OR 1 or -NR 2 R 3.
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an organic group.
• R 1 and Ra, R 2 and Ra, and R 2 and R 3 may each be linked to each other to form a ring.
• Y1 and Y2 each independently represent a substituent. * represents the bonding position to the main chain.
• the SP values of the compound represented by the following formula (U-2H) and the compound represented by the following formula (U-3H) in which a hydrogen atom is bonded to * are each 21 MPa 1/2 or more.
• Y 1 and Y 2 have the same meanings as Y 1 and Y 2 in the above formulae (U-2) and (U-3), respectively.
• Y1 and Y2 each independently represent a substituent. * represents the bonding position to the main chain.
• the SP values of the compound represented by the following formula (U-2H) and the compound represented by the following formula (U-3H) in which a hydrogen atom is bonded to * are each 21 MPa 1/2 or more.
• An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin and a solvent, The resin includes a main chain including a repeating unit represented by the following formula (2) and an end group bonded to the main chain, An actinic ray-sensitive or radiation-sensitive resin composition, wherein at least one of the terminal groups contains a group represented by any one of the following formulas (T-1) to (T-7):
• the resist composition of the present invention contains a resin (hereinafter also referred to as a “specific resin”) that contains a main chain that is decomposable when irradiated with actinic rays or radiation, and a terminal group represented by formula (U-1) bonded to the main chain.
• a resin hereinafter also referred to as a “specific resin” that contains a main chain that is decomposable when irradiated with actinic rays or radiation, and a terminal group represented by formula (U-1) bonded to the main chain.
• 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 case where the specific resin contains a group represented by -CO-N(R q )-, -CO-N(R q )-CO- or -SO 2 -N(R q )- as a specific functional group corresponds to, for example, a case where Ra and R 2 or R 3 in the repeating unit represented by formula (1) above are linked to each other to form a ring, and the ring has a structural moiety represented by -CO-N(R q )-, a structural moiety represented by -CO-N(R q )-CO- or a structural moiety represented by -SO 2 -N(R q )-.
• the main chain of the specific resin preferably contains a repeating unit containing a specific functional group.
• the content of the repeating unit containing the specific functional group in the main chain of the specific resin is preferably 5 to 100 mol %, more preferably 10 to 100 mol %, and even more preferably 20 to 100 mol %, based on all repeating units in the main chain of the specific resin.
• the repeating unit containing the specific functional group may be one type or two or more types. When the repeating unit containing the specific functional group is two or more types, the total content thereof is preferably within the above numerical range.
• Y 0 represents a hydrogen atom or a substituent
• L 0 represents a divalent linking group not containing a monomer unit
• * represents the bonding position to the main chain.
• the SP value of the compound represented by the following formula (U-1H) in which a hydrogen atom is bonded to * is 21 MPa 1/2 or more.
• the aromatic ring of the nitrogen-containing aromatic group may be a monocyclic ring or a polycyclic ring.
• the number of nitrogen atoms contained in the aromatic ring of the nitrogen-containing aromatic group is not particularly limited, but is preferably 1 to 4, and more preferably 1 or 2.
• Examples of the aromatic ring of the nitrogen-containing aromatic group include nitrogen-containing aromatic rings having 2 to 20 carbon atoms.
• the aromatic ring may have a substituent.
• the substituent is not particularly limited, but examples thereof include a hydroxyl group and a cyano group. Examples of groups having a nitrogen-containing aromatic group include nitrogen-containing aromatic groups, and groups in which a nitrogen-containing aromatic group is substituted on an alkyl group or a cycloalkyl group.
• Examples of the group having an acidic group having an acidic proton include an acidic group having an acidic proton, and a group in which an acidic group having an acidic proton is substituted on an alkyl group, a cycloalkyl group, or an aryl group.
• Each of the above R and R Q independently represents a substituent
• R P represents an alkyl group, an aryl group, or a nitrogen-containing aromatic group.
• Examples of groups having a polar group include polar groups, and groups in which a polar group is substituted on an alkyl group, a cycloalkyl group, or an aryl group.
• the substituent represented by Y 0 may be a group (ie, a polymer chain) that includes one or more monomer units.
• the specific end group in which Y 0 is a polymer chain is also called a high molecular type specific end group, whereas the specific end group in which Y 0 is not a polymer chain is also called a low molecular type specific end group.
• the monomer unit contained in the polymer chain is not particularly limited, but is preferably, for example, a monomer unit represented by the following formula (G-1).
• R S1 and R S2 each independently represent a hydrogen atom or an alkyl group
• R S3 represents a group containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
• R S1 and R S2 each independently represent a hydrogen atom or an alkyl group.
• the alkyl group may be either linear or branched.
• the number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 3.
• the alkyl group may have a substituent.
• R S3 represents a group containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
• Preferred examples of R S3 include the above-mentioned groups having a nitrogen-containing aromatic group, groups having an acidic group having an acidic proton, and groups having a polar group.
• L 0 represents a divalent linking group not containing a monomer unit.
• the term "monomer unit” refers to a structural unit obtained by polymerization of a monomer.
• L 0 include a divalent hydrocarbon group, -O-, -CO-, -S-, -SO-, -SO 2 -, -NR 0 -, -N ⁇ CR 0 -, a divalent heterocyclic group, and a divalent linking group formed by combining these.
• R 0 represents a hydrogen atom or an organic group.
• Examples of the divalent hydrocarbon group include an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, and an arylene group.
• the alkylene group may be linear or branched, and preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms.
• the cycloalkylene group may be a monocyclic or polycyclic group, and preferably has 3 to 20 carbon atoms, and more preferably has 5 to 12 carbon atoms.
• the alkenylene group may be linear or branched, and preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms.
• the alkynylene group may be linear or branched, and preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms.
• the arylene group preferably has 6 to 20 carbon atoms, and more preferably has 6 to 12 carbon atoms.
• the divalent hydrocarbon group may have a substituent.
• the divalent heterocyclic group includes a divalent heterocyclic group containing at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.
• the divalent heterocyclic group may be an aromatic group or a non-aromatic group.
• the number of carbon atoms in the divalent heterocyclic group is preferably 2 to 10, more preferably 2 to 6.
• the divalent heterocyclic group may have a substituent.
• the organic group represented by R0 is preferably an alkyl group.
• the alkyl group may be linear or branched.
• the number of carbon atoms in the alkyl group is preferably 1 to 12, and more preferably 1 to 6.
• the alkyl group may have a substituent.
• L 0 include the following divalent linking groups or divalent linking groups formed by combining two or more of the following divalent linking groups:
• * represents a bonding position.
• a divalent linking group as a part of the main chain skeleton of a polymer chain formed by repeatedly linking one or more types of monomer units does not fall under L0 (such a divalent linking group is not treated as L0 ).
• kx1, kx2, and kx3 surrounded by dotted lines which are part of the main chain skeleton of a polymer chain represented by the following formula (px-1), which is composed of a monomer unit represented by the following formula (mx-1) and a monomer unit represented by the following formula (mx-2), are not treated as L0 .
• * represents a bonding site.
• the terminal group represented by formula (U-1) is also preferably a group represented by the following formula (U-30).
• R U1 and R U2 each independently represent a hydrogen atom or an organic group. R U1 and R U2 may be bonded to form a ring. L U1 represents an oxygen atom or a single bond. Y 2 represents a substituent. * represents the bonding position to the main chain. However, the SP value of the compound represented by the following formula (U-30H) in which a hydrogen atom is bonded to * is 21 MPa 1/2 or more.
• Y2 has the same meaning as Y2 in the above formula (U-30).
• terminal group represented by formula (U-1) is at least one selected from the group consisting of a group represented by the following formula (U-2) and a group represented by the following formula (U-3).
• Y1 and Y2 each independently represent a substituent. * represents the bonding position to the main chain.
• the SP values of the compound represented by the following formula (U-2H) and the compound represented by the following formula (U-3H) in which a hydrogen atom is bonded to * are each 21 MPa 1/2 or more.
• At least one of the specific terminal groups of the specific resin contains a group represented by any one of the following formulas (T-1) to (T-7).
• T-1) to (T-7) a group represented by any one of the following formulas (T-1) to (T-7).
• Y 0, which is a polymer chain contains a group represented by any one of the following formulas (T-1) to (T-7)
• L 0 contains a group represented by any one of the following formulas (T-1) to (T-7).
• L T1 to L T8 each independently represent a single bond or a divalent linking group.
• AN represents a nitrogen-containing aromatic group.
• K 1 represents a ring containing CO and N.
• Q 1 represents a sulfonic acid group, an alkylcarbonyl group, an arylcarbonyl group, a cyano group, a carboxyl group, a hydroxyl group, -CO-NQ 8 Q 9 , -SO 2 -NQ 8 Q 9 , -CO-NQ 8 -CO-Q 9 , -CO-NQ 8 -SO 2 -Q 9 , -SO 2 -NQ 8 -CO-Q 9 , or -SO 2 -NQ 8 -SO 2 -Q 9.
• L T1 to L T8 each independently represent a single bond or a divalent linking group.
• the divalent linking groups represented by L T1 to L T8 include divalent hydrocarbon groups, -O-, -CO-, -S-, -SO-, -SO 2 -, -NR 0 -, -N ⁇ CR 0 -, divalent heterocyclic groups, and divalent linking groups formed by combining these.
• R 0 represents a hydrogen atom or an organic group.
• the divalent hydrocarbon group include an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, and an arylene group.
• the divalent heterocyclic group includes a divalent heterocyclic group containing at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.
• the divalent heterocyclic group may be an aromatic group or a non-aromatic group.
• the number of carbon atoms in the divalent heterocyclic group is preferably 2 to 10, more preferably 2 to 6.
• the divalent heterocyclic group may have a substituent.
• the organic group represented by R0 is preferably an alkyl group.
• the alkyl group may be linear or branched.
• the number of carbon atoms in the alkyl group is preferably 1 to 12, and more preferably 1 to 6.
• the alkyl group may have a substituent.
• L T2 represents a single bond or a divalent linking group.
• R k represents a hydrogen atom or a substituent.
• R j represents a substituent.
• j represents an integer of 0 to 4. When a plurality of R k and R j are present, the plurality of R k and R j may be the same or different.
• the SP value is the Hansen solubility parameter, which is derived using the Hansen method, which expresses the energy of a substance as three components, namely, a dispersion energy term ( ⁇ D ), a polarization energy term ( ⁇ P ), and a hydrogen bond energy term ( ⁇ H ), and expresses them as vectors in a three-dimensional space.
• the SP value is a value calculated by the software Hansen Solubility Parameters in Practice (HSPiP) ver. 4.1.07.
• the polymer chain represented by Y0 of the polymeric specific terminal group is composed of n types of monomer units, the number of monomer units of each type is m i , and the total number of monomer units of all monomer units (total number) is m A.
• n is an integer of 1 or more, and i is an integer from 1 to n. That is, the relationship of the following mathematical formula (F1) is established.
• a monomer corresponding to a monomer unit refers to a structure obtained when the polymerizable group of the monomer is considered to have polymerized, which is the structure of the monomer unit, and the monomer unit does not necessarily have to be one actually obtained using the monomer (for example, the monomer unit may be obtained by changing the structure by a chemical reaction after performing a polymerization reaction using another monomer).
• the dispersion energy term ( ⁇ D ), polarization energy term ( ⁇ P ), hydrogen bond energy term ( ⁇ H ), and SP values of W-1 to W-57 are shown in Tables 2 and 3 below.
• the content of the specific resin is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 65% by mass or more, and particularly preferably 70% by mass or more, based on the total solid content of the resist composition.
• the upper limit of the content of the specific resin is not particularly limited, and may be 100% by mass or less, 99% by mass or less, or 97% by mass or less.
• the specific resin may be used alone or in combination. When two or more types are used, the total content is preferably within the above-mentioned suitable content range.
• alkoxypropionate methyl 3-methoxypropionate (MMP) or ethyl 3-ethoxypropionate (EEP) is preferred.
• chain ketone 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, acetone, 2-heptanone, 4-heptanone, 1-hexanone, 2-hexanone, diisobutyl ketone, phenylacetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone, acetonylacetone, ionone, diacetonyl alcohol, acetylcarbinol, acetophenone, methyl naphthyl ketone, or methyl amyl ketone is preferred.
• the organic acid generated by decomposition of the photodecomposable onium salt compound by exposure is a polyvalent acid having two or more acid groups.
• Examples of the alkyl group and cycloalkyl group for R 201 to R 203 include linear alkyl groups having 1 to 10 carbon atoms or branched alkyl groups having 3 to 10 carbon atoms (e.g., methyl, ethyl, propyl, butyl, and pentyl groups), and cycloalkyl groups having 3 to 10 carbon atoms (e.g., cyclopentyl, cyclohexyl, and norbornyl groups).
• R 201 to R 203 may be further substituted with a halogen atom, an alkoxy group (eg, having 1 to 5 carbon atoms), a hydroxyl group, a cyano group, or a nitro group.
• 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 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, for example, 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.
• it is also preferable that the atom in R X1 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 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 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 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 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 photodecomposable 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 photodecomposable 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 cationic moiety M 1 + and the cationic moiety M 2 + are structural moieties containing a positively charged atom or atomic group, and examples thereof include organic cations having a monovalent charge.
• the organic cation is not particularly limited, but is preferably an organic cation represented by the above formula (ZaI) (cation (ZaI)) or an organic cation represented by the above formula (ZaII) (cation (ZaII)).
• Compound (II) is a compound having two or more of the above structural moieties X and one or more of the following structural moieties Z, and is a compound that generates an acid containing two or more of the first acidic moieties derived from the structural moiety X and the structural moiety Z when irradiated with actinic rays or radiation.
• Structural moiety Z a non-ionic moiety capable of neutralizing an acid
• 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.
• the nonionic moiety capable of neutralizing an acid in the structural moiety Z is not particularly limited, and is preferably, for example, a moiety containing a functional group having an electron or a group capable of electrostatically interacting with a proton.
• functional groups having a group or electrons capable of electrostatically interacting with a proton include functional groups having a macrocyclic structure such as cyclic polyether, or functional groups having a nitrogen atom having an unshared electron pair that does not contribute to ⁇ conjugation.
• the nitrogen atom having an unshared electron pair that does not contribute to ⁇ conjugation is, for example, a nitrogen atom having a partial structure shown in the following formula:
• Y 0 and L 0 respectively have the same meanings as Y 0 and L 0 in the above formula (U-1).
• the terminal group represented by the above formula (U-1) is preferably at least one selected from the group consisting of a group represented by the following formula (U-2) and a group represented by the following formula (U-3).
• An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin and a solvent,
• the resin includes a main chain including a repeating unit represented by the following formula (2) and an end group bonded to the main chain,
• the actinic ray-sensitive or radiation-sensitive resin composition has at least one of the terminal groups containing a group represented by any one of the following formulas (T-1) to (T-7). The details of each component and each formula are as described above.
• L T1 to L T8 each independently represent a single bond or a divalent linking group.
• AN represents a nitrogen-containing aromatic group.
• K 1 represents a ring containing CO and N.
• Q 1 represents a sulfonic acid group, an alkylcarbonyl group, an arylcarbonyl group, a cyano group, a carboxyl group, a hydroxyl group, -CO-NQ 8 Q 9 , -SO 2 -NQ 8 Q 9 , -CO-NQ 8 -CO-Q 9 , -CO-NQ 8 -SO 2 -Q 9 , -SO 2 -NQ 8 -CO-Q 9 , or -SO 2 -NQ 8 -SO 2 -Q 9.
• the present invention also relates to a resist film formed using the above resist composition, and a pattern forming method using the above resist film.
• the pattern forming method of the present invention is preferably a pattern forming method comprising the steps of forming a film using the resist composition, exposing the film to light, and developing the exposed film using a developer.
• Step 1 is a step of forming a resist film on a substrate using a resist composition.
• the resist composition can be applied onto a substrate (e.g., silicon, silicon coated with silicon dioxide) such as those used in the manufacture of integrated circuit elements by a suitable application method such as a spinner or coater.
• the application method is preferably spin coating using a spinner.
• the rotation speed when spin coating using a spinner is preferably 1000 to 3000 rpm (rotations per minute).
• the substrate may be dried to form a resist film. If necessary, various undercoats (inorganic films, organic films, anti-reflective films) may be formed under the resist film.
• a top coat may be formed on the resist film using a top coat composition. It is preferable that the top coat composition does not mix with the resist film and can be uniformly applied to the upper layer of the resist film.
• the top coat is not particularly limited, and a conventionally known top coat can be formed by a conventionally known method. For example, a top coat can be formed based on the description in paragraphs [0072] to [0082] of JP2014-059543A. For example, it is preferable to form a top coat containing a basic compound as described in JP-A-2013-061648 on the resist film.
• the heating temperature is preferably from 80 to 150°C, more preferably from 80 to 140°C, and even more preferably from 80 to 130°C.
• the heating time is preferably from 10 to 1,000 seconds, more preferably from 10 to 180 seconds, and even more preferably from 30 to 120 seconds. Heating can be carried out by a means provided in a normal exposure machine and/or developing machine, and may be carried out using a hot plate or the like.
• Step 3 is a step of developing the exposed resist film with a developer to form a pattern.
• the developer may be an alkaline developer or a developer containing an organic solvent (hereinafter also referred to as an organic developer), but is preferably an organic developer.
• the development time is not particularly limited as long as the resin in the unexposed area is sufficiently dissolved, and is preferably from 10 to 300 seconds, more preferably from 20 to 120 seconds.
• the temperature of the developer is preferably from 0 to 50°C, and more preferably from 15 to 35°C.
• the alkaline developer is preferably an aqueous alkaline solution containing an alkali.
• aqueous alkaline solution containing an quaternary ammonium salt such as tetramethylammonium hydroxide, an inorganic alkali, a primary amine, a secondary amine, a tertiary amine, an alcohol amine, or a cyclic amine.
• the alkaline developer is preferably an aqueous solution of a quaternary ammonium salt such as tetramethylammonium hydroxide (TMAH).
• TMAH tetramethylammonium hydroxide
• Appropriate amounts of alcohols, surfactants, etc. may be added to the alkaline developer.
• the alkaline concentration of the alkaline developer is preferably 0.1 to 20% by mass.
• the pH of the alkaline developer is preferably 10.0 to 15.0.
• the organic developer preferably contains at least one organic solvent selected from the group consisting of ketone solvents, ester solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents.
• the above-mentioned solvents may be mixed in combination, or may be mixed with a solvent other than the above or with water.
• the water content of the developer as a whole is preferably less than 50% by mass, more preferably less than 20% by mass, even more preferably less than 10% by mass, and particularly preferably substantially free of water.
• the content of the organic solvent in the organic developer is preferably 50% by mass or more and 100% by mass or less, more preferably 80% by mass or more and 100% by mass or less, still more preferably 90% by mass or more and 100% by mass or less, and particularly preferably 95% by mass or more and 100% by mass or less, based on the total amount of the developer.
• the rinse liquid used in the rinse step following the step of developing with an alkaline developer is, for example, pure water, to which an appropriate amount of a surfactant may be added.
• a suitable amount of a surfactant may be added to the rinse solution.
• the rinse liquid used in the rinse step following the development step using an organic developer is not particularly limited as long as it does not dissolve the pattern, and a solution containing a general organic solvent can be used. It is preferable to use a rinse liquid containing at least one organic solvent selected from the group consisting of hydrocarbon solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents, and ether solvents.
• A-1 to A-33 and B-1 to B-6 shown in Table 4 below were used as the resins.
• the main chain of each resin contains the repeating units 1 to 3 shown in Table 4 in the content (mol%) shown in Table 4.
• the content of the repeating units 1 to 3 is the molar content of each repeating unit with respect to the total repeating units in the main chain.
• the main chain of each resin is bonded to the terminal group shown in Table 4.
• Table 4 lists the SP value and molecular weight of the terminal group (number average molecular weight measured by GPC in the case of a polymer-type specific terminal group).
• an actinic ray-sensitive or radiation-sensitive resin composition having excellent sensitivity and resolution. Furthermore, according to the present invention, there can be provided a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition, a pattern forming method using the actinic ray-sensitive or radiation-sensitive resin composition, and a method for producing an electronic device.

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• 2023
  • 2023-12-20 WO PCT/JP2023/045815 patent/WO2024147289A1/ja not_active Ceased
  • 2023-12-20 JP JP2024568896A patent/JPWO2024147289A1/ja active Pending
• 2024
  • 2024-01-03 TW TW113100183A patent/TW202436390A/zh unknown

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