Classifications

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  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/28—Phosphorus compounds with one or more P—C bonds
  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
  • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
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  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
  • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
  • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
  • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
  • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
  • C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
  • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
  • C07C243/10—Hydrazines
  • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
  • C07C243/14—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of a saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
  • C07C309/01—Sulfonic acids
  • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
  • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
  • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
  • C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
  • C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
  • C07C309/01—Sulfonic acids
  • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
  • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/28—Phosphorus compounds with one or more P—C bonds
  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
  • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
  • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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  • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F12/02—Monomers containing only one unsaturated aliphatic radical
  • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
  • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
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  • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F12/02—Monomers containing only one unsaturated aliphatic radical
  • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
  • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
  • C08F12/22—Oxygen
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  • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F12/02—Monomers containing only one unsaturated aliphatic radical
  • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
  • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
  • C08F12/26—Nitrogen
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  • C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
  • C08F126/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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  • 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
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  • 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
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  • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
  • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
  • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
  • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
  • C23C16/455—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
  • C23C16/45523—Pulsed gas flow or change of composition over time
  • C23C16/45525—Atomic layer deposition [ALD]
  • C23C16/45527—Atomic layer deposition [ALD] characterized by the ALD cycle, e.g. different flows or temperatures during half-reactions, unusual pulsing sequence, use of precursor mixtures or auxiliary reactants or activations
  • C23C16/45534—Use of auxiliary reactants other than used for contributing to the composition of the main film, e.g. catalysts, activators or scavengers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
  • H10P14/00—Formation of materials, e.g. in the shape of layers or pillars
  • H10P14/60—Formation of materials, e.g. in the shape of layers or pillars of insulating materials
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
  • H10P14/00—Formation of materials, e.g. in the shape of layers or pillars
  • H10P14/60—Formation of materials, e.g. in the shape of layers or pillars of insulating materials
  • H10P14/63—Formation of materials, e.g. in the shape of layers or pillars of insulating materials characterised by the formation processes
  • H10P14/6326—Deposition processes
  • H10P14/6328—Deposition from the gas or vapour phase
  • H10P14/6334—Deposition from the gas or vapour phase using decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
  • H10P14/6339—Deposition from the gas or vapour phase using decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition deposition by cyclic CVD, e.g. ALD, ALE or pulsed CVD
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
  • H10P14/00—Formation of materials, e.g. in the shape of layers or pillars
  • H10P14/60—Formation of materials, e.g. in the shape of layers or pillars of insulating materials
  • H10P14/68—Organic materials, e.g. photoresists
  • H10P14/683—Organic materials, e.g. photoresists carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC

Definitions

• the present invention relates to a composition, a compound, a method for producing a modified substrate, and a method for producing a semiconductor device for processing a semiconductor device.
• Patent Document 1 describes a related technology using ALD as a substrate processing method that can solve at least one of the problems of selectively forming a film on a substrate and suppressing metal residue after film formation, as "a substrate processing method for polymerizing a monomer on a substrate to form a polymer film, the substrate processing method including a step of supplying the monomer that chemically bonds with the substrate onto the substrate, and a step of supplying an initiator that polymerizes the monomer onto the substrate to which the monomer has been supplied.”
• a method for forming a fine pattern on a substrate having a plurality of regions made of different materials on its surface (for example, a metal region containing metal atoms and an insulating region containing an insulator), in which one of the regions is modified to form a film (modified film), and then an ALD process is performed, thereby forming an ALD film in the region where the modified film is not formed, without forming a coating by ALD (ALD coating).
• ALD ALD coating
• the present inventors referring to the substrate processing method described in Patent Document 1, formed a polymer film as the modification film, and then attempted to form an ALD coating on the region where the modification film was not formed, but a thick ALD coating was formed even on the region where the modification film was formed (on the modification film). In other words, it became clear that the polymer film obtained by using the monomer used in the substrate processing method described in Patent Document 1 cannot sufficiently inhibit the formation of the ALD coating, and further improvement is necessary.
• a method for producing a liquid crystal display comprising: a compound having a specific functional group capable of binding to or adsorbing on a substrate and a polymerizable group; and a solvent;
• the specific functional group is a basic functional group or an acidic functional group, when the specific functional group is the basic functional group, the acid dissociation constant of a conjugate acid of the compound obtained by adding a proton to the basic functional group is 7.0 or more;
• the specific functional group is an acidic functional group, the compound has an acid dissociation constant of 5.0 or less when a proton dissociates from the acidic functional group.
• the basic functional group is a primary amino group, a secondary amino group, or a tertiary amino group.
• the acidic functional group is a phosphonic acid group, a sulfo group, or a carboxy group.
• composition for treating a semiconductor device according to any one of [1] to [5], wherein the acidic functional group is a phosphonic acid group or a sulfo group.
• the polymerizable group is an ethylenically unsaturated group.
• the polymerizable group is an aromatic vinyl group, an acryloyloxy group, a methacryloyloxy group, an acrylamide group, a methacrylamide group, a maleimide group, or a vinyl ether group.
• composition for treating a semiconductor device according to any one of [1] to [8], wherein the polymerizable group is a styryl group or a vinyl naphthyl group.
• the polymerizable group is a styryl group or a vinyl naphthyl group.
• the composition for treating a semiconductor device according to any one of [1] to [9], wherein the compound is a compound represented by general formula (1) described below.
• the composition for treating a semiconductor device according to any one of [1] to [9], wherein the compound is a compound represented by general formula (4) described below.
• a method for producing a modified substrate comprising: a step 2 of subjecting the substrate obtained in the step 1 to an atomic layer deposition process (ALD process) to form a second film on the second surface.
• a method for producing a semiconductor device comprising the method for producing a modified substrate according to [18].
• the present invention provides compositions for semiconductor device processing that are capable of forming films that are highly inhibitory to ALD film formation. Furthermore, the present invention can provide a method for producing a compound, a modified substrate, and a method for producing a semiconductor device.
• total solids content refers to the total content of all components contained in a composition other than water and solvents such as organic solvents.
• the compounds described herein may contain structural isomers, optical isomers, and isotopes. In addition, the compounds may contain one or more structural isomers, optical isomers, and isotopes.
• the bonding direction of a divalent group may be either "X-O-CO-Z" or "X-CO-O-Z" when Y in a compound represented by "X-Y-Z” is -COO-.
• pKa is a value calculated using the following software package 1 based on a database of Hammett's substituent constants and known literature values.
• Software package 1 Advanced Chemistry Development (ACD/Labs)
• Software V8.14 for Solaris (1994-2007 ACD/Labs) a value obtained by a molecular orbital calculation method is used.
• a value obtained using Gaussian 16 based on DFT is used.
• the molecular weight of a compound having a molecular weight distribution is the weight average molecular weight.
• the composition for semiconductor device treatment of the present invention (hereinafter, also simply referred to as "the composition") will be described in detail below.
• the composition is a composition for semiconductor device treatment comprising a compound having a specific functional group capable of binding to or adsorbing to a substrate and a polymerizable group, and a solvent, wherein the specific functional group is a basic functional group or an acidic functional group, and when the specific functional group is a basic functional group, the acid dissociation constant of the conjugate acid of the compound obtained by adding a proton to the basic functional group is 7.0 or more, and when the specific functional group is an acidic functional group, the acid dissociation constant of the compound when a proton dissociates from the acidic functional group is 5.0 or less.
• the mechanism by which the problem of the present invention can be solved by the composition having the above-mentioned structure is not necessarily clear, but the present inventors speculate as follows.
• the mechanism by which the effects are obtained is not limited by the following speculation. In other words, even if the effects are obtained by a mechanism other than the following, it is included in the scope of the present invention.
• the specific functional group has an acid dissociation constant of the conjugate acid of the specific compound or an acid dissociation constant of the specific compound within a specified range, and therefore can selectively bind to or adsorb to a specific region on the substrate, thereby forming a film consisting of the specific compound in a region-selective manner. Furthermore, since the specific compound has a polymerizable group, when the substrate is heated in the ALD process, a reaction occurs between the polymerizable groups to form covalent bonds, and the film is cured to obtain a coating that is a cured film.
• compositions for treating semiconductor devices of the present invention are described in detail below.
• the ability of the composition to form a coating that has a higher inhibitory effect on ALD coating formation is also referred to as "the effect of the present invention being superior.”
• compositions for Processing Semiconductor Devices includes a compound (specific compound) having a specific functional group capable of binding or adsorbing to a substrate and a polymerizable group, and a solvent.
• the specific compound is a compound having a specific functional group and a polymerizable group.
• the bonding positions of each group are not particularly limited, but it is preferable that the specific functional group is at one end of the molecule and the polymerizable group is at the other end of the molecule.
• the specific functional group is a functional group that bonds to or adsorbs to a substrate, and may form any bond or interaction with the substrate, such as a covalent bond, a coordinate bond, an ionic bond, a hydrogen bond, a van der Waals bond, or a metallic bond.
• the specific functional group is preferably a functional group that bonds to or is adsorbed onto a surface containing a metal atom, and more preferably a functional group that bonds to or is adsorbed onto a metal surface.
• the metal may be, for example, a transition metal, and is preferably copper, cobalt, titanium, tantalum, tungsten, ruthenium, or molybdenum.
• the acid dissociation constant (hereinafter also referred to as "pKa(b)") of the conjugate acid of the specific compound obtained by adding a proton to the basic functional group is 7.0 or more.
• the specific compound is compound E-3 shown below, the equilibrium state with respect to pKa(b) is represented by the following dissociation equilibrium formula, and pKa(b) is 8.2.
• the pKa(b) When the pKa(b) is 7.0 or more, the specific functional group is easily adsorbed or bonded to a substrate (particularly, a substrate having a tungsten surface or a ruthenium surface), and a coating exhibiting predetermined properties is easily and stably formed on the substrate.
• the pKa(b) is preferably 8.0 or more, more preferably 9.0 or more, and even more preferably 10.0 or more. There is no particular upper limit, but it is preferably 30.0 or less.
• the basic functional group examples include nitrogen-containing groups.
• the basic functional group is preferably an amino group, a hydrazine group, or a guanidine group, more preferably a primary amino group, a secondary amino group, or a tertiary amino group, and even more preferably a primary amino group.
• the amino group contained in the hydrazine group or guanidine group is not included in the above amino group (primary amino group, secondary amino group, or tertiary amino group). That is, the hydrazine group and the guanidine group in this specification are treated as groups different from amino groups.
• the nitrogen-containing group may be a group obtained by removing one hydrogen atom from an alicyclic amine.
• Examples of the alicyclic amine include pyrrolidine, piperidine, morpholine, 1,4-diazabicyclo[2.2.2]octane (DABCO (registered trademark)), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU (registered trademark)), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene.
• examples of the nitrogen-containing group include a group formed by removing one hydrogen atom from 2-methylimidazole.
• the basic functional group is preferably a group represented by any one of formulas (S1) to (S3).
• * represents the bond position.
• each R 1 T independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
• a plurality of R 1 -T may be bonded to each other to form a ring.
• the ring formed is a ring containing a nitrogen atom, and examples thereof include a pyrrolidine ring, a piperidine ring, and a piperazine ring.
• the acid dissociation constant (hereinafter also referred to as "pKa(a)") of the specific compound when a proton dissociates from the acidic functional group is 5.0 or less.
• the specific compound is the following compound E-15
• the equilibrium state with respect to pKa(a) is represented by the following dissociation equilibrium formula, and pKa(a) is 4.8.
• the pKa(a) When the pKa(a) is 5.0 or less, the specific functional group is easily adsorbed or bonded to a substrate (particularly a substrate having a copper surface), and a coating exhibiting predetermined properties is easily and stably formed on the substrate.
• the pKa(a) is preferably 4.0 or less, more preferably 3.5 or less, and even more preferably 3.0 or less. There is no particular lower limit, but it is preferably ⁇ 5.0 or more.
• the acidic functional group examples include a phosphoric acid group (-PO 4 H 2 ), a phosphonic acid group (-PO 3 H 2 ), a sulfo group (-SO 3 H), a carboxy group (-COOH), and salts thereof.
• the acidic functional group is preferably a phosphonic acid group, a sulfo group, or a carboxy group, and more preferably a phosphonic acid group or a sulfo group.
• the salt of a phosphate group refers to a group represented by -PO 4 2- Ct n+ 2/n .
• Ct n+ represents an n-valent cation, where n represents 1 or 2.
• monovalent cations include Li + , Na + , K + , and NH 4 + .
• divalent cations include Mg 2+ and Ca 2+ .
• Ct n+ represents a divalent cation, the number is one.
• a compound having a phosphate group is also called a "phosphate compound" and the functional group name is also called "-phosphate".
• the salt of a phosphonic acid group refers to a group represented by -PO 3 2- Ct n+ 2/n , where Ct n+ represents an n-valent cation, where n is 1 or 2.
• Examples of the monovalent cation and the divalent cation include the same cations as those explained above for the salt of a phosphate group, and the numbers thereof are also the same.
• a compound having a phosphonic acid group is also called a "phosphonic acid compound.”
• the salt of a sulfo group refers to a group represented by -SO 3 - Ct + , where Ct + represents a monovalent cation, and examples of the monovalent cation include the same cations as those explained above for the salt of a phosphate group.
• the salt of a carboxy group refers to a group represented by -COO - Ct + , where Ct + represents a monovalent cation, and examples of such a cation include the same monovalent cations as those explained above for the salt of a phosphate group.
• the number of specific functional groups possessed by the specific compound is not particularly limited as long as it is 1 or more, but 1 to 3 is preferable, and 1 or 2 is more preferable.
• the polymerizable group is not particularly limited, but is preferably one that undergoes polymerization reaction by heating. After forming a film made of a specific compound on a substrate, the polymerizable groups are reacted with each other by heat treatment, so that the film made of the specific compound becomes a film that has excellent heat resistance and high inhibition of ALD film formation. In addition, since the film has excellent heat resistance, the process window in the semiconductor device processing process can be expanded.
• the polymerizable group include a radical polymerizable group, a cationic polymerizable group, and an anionic polymerizable group, and an ethylenically unsaturated group is preferred.
• the ethylenically unsaturated group is a functional group having an ethylenically unsaturated bond.
• the polymerizable group is preferably an aromatic vinyl group, an acryloyloxy group (CH 2 ⁇ CH-COO-), a methacryloyloxy group (CH 2 ⁇ CCH 3 -COO-), an acrylamide group (CH 2 ⁇ CH-CONH-), a methacrylamide group (CH 2 ⁇ CCH 3 -CONH-), a maleimide group, a vinyl group, or a vinyl ether group, and more preferably a styryl group or a vinyl naphthyl group.
• the aromatic vinyl group refers to a group in which a hydrogen atom on an aryl group or a heteroaryl group is substituted with a vinyl group.
• a styryl group or a vinylnaphthyl group is preferred as the aromatic vinyl group.
• the vinylnaphthyl group is preferably a group obtained by removing the hydrogen atom at the 6-position from 2-vinylnaphthalene.
• each of the groups exemplified above as the polymerizable group is treated as a group different from a vinyl group (CH 2 ⁇ CH—).
• each of the groups exemplified above as the polymerizable group includes a structure represented by CH 2 ⁇ CH—, but is treated as a group different from a vinyl group.
• the number of polymerizable groups possessed by the specific compound is not particularly limited as long as it is 1 or more, but 1 to 3 is preferred, and 1 or 2 is more preferred.
• the specific compound preferably has a structure exhibiting orientation, which means a structure having a function of orienting the specific compound in a direction perpendicular to a substrate when the composition is brought into contact with a substrate to form a film of the specific compound on the substrate.
• the structure exhibiting orientation is not particularly limited, and examples thereof include divalent aliphatic hydrocarbon groups which may have an ethereal oxygen atom or -CO-, divalent aromatic ring groups, and groups formed by combining these. Among these, divalent aliphatic hydrocarbon groups which may have an ethereal oxygen atom are preferred.
• the divalent aliphatic hydrocarbon group may be linear, branched, or cyclic, but is preferably linear.
• Examples of the divalent aliphatic hydrocarbon group include an alkylene group, an alkenylene group, and an alkynylene group, and an alkylene group is preferred.
• the number of carbon atoms in the divalent aliphatic hydrocarbon group is not particularly limited, but from the viewpoint of improving the stability of the film made of the specific compound on the substrate, it is preferably 6 to 30, more preferably 8 to 28, and even more preferably 10 to 24.
• the divalent aromatic ring group may be either a divalent aromatic hydrocarbon group (arylene group) or a divalent aromatic heterocyclic group (heteroarylene group), with an arylene group being preferred.
• the divalent aromatic ring group may be either a monocyclic or polycyclic group.
• the divalent aromatic ring group preferably has 5 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
• the arylene group may be, for example, a phenylene group.
• the arylene group may also be a structure in which a plurality of aromatic hydrocarbon rings are bonded via single bonds, such as a biphenyl structure.
• An example of a heteroarylene group is a group formed by removing two hydrogen atoms from pyridine.
• the specific compound is preferably a compound represented by general formula (S1), and more preferably a compound represented by general formula (1).
• X1 represents an amino group, a hydrazine group, a guanidine group, a phosphonic acid group, a sulfo group, or a carboxy group. Specific and preferred embodiments of each group represented by X 1 are as described above for the specific functional group. As each group represented by X 1 , a primary amino group is particularly preferred.
• Y1 represents an ethylenically unsaturated group.
• the ethylenically unsaturated group represented by Y1 is preferably a styryl group, a vinylnaphthyl group, an acryloyloxy group, a methacryloyloxy group, an acrylamide group, a methacrylamide group, a maleimide group, a vinyl group, or a vinyl ether group.
• L1 represents a divalent aliphatic hydrocarbon group which may have an etheric oxygen atom or -CO-, a divalent aromatic ring group, or a group formed by combining these.
• the divalent aliphatic hydrocarbon group is preferably an alkylene group which may have an etheric oxygen atom.
• the alkylene group preferably has 1 to 30 carbon atoms.
• the divalent aromatic ring group is preferably a phenylene group.
• X represents a primary amino group, a phosphonic acid group, or a sulfo group.
• L1 represents a single bond or an alkylene group which may have an etheric oxygen atom.
• Ar 1 represents an arylene group.
• the alkylene group which may have an etheric oxygen atom and is represented by L1 may be any of linear, branched and cyclic, but is preferably linear.
• the alkylene group which may have an etheric oxygen atom preferably has 6 to 30 carbon atoms, more preferably 8 to 28 carbon atoms, and even more preferably 10 to 24 carbon atoms.
• the alkylene group which may have an etheric oxygen atom, represented by L1 is preferably a group represented by formula (1a) or formula (1b).
• L 1a and L 1b each independently represent an alkylene group having 1 to 25 carbon atoms.
• the aromatic hydrocarbon ring constituting the arylene group represented by Ar 1 may be either a monocyclic ring or a polycyclic ring (a structure in which a plurality of monocyclic rings are condensed). In addition, it may be a structure in which a plurality of aromatic hydrocarbon rings are bonded via a single bond, such as a biphenyl structure. In other words, the arylene group may be a biphenyl group.
• the arylene group preferably has 6 to 20 carbon atoms, and more preferably has 6 to 12 carbon atoms.
• a group represented by any one of the following formulae (2-1) to (2-3) is preferable.
• the specific compound is more preferably a compound represented by general formula (2) or a compound represented by general formula (3).
• Y 1 represents —O— or —OCH 2 —.
• Ar2 represents a group represented by any one of formulas (2-1) to (2-3). n represents an integer of 5 or more. * indicates the bond position.
• n is not particularly limited as long as it is 5 or more, but is preferably 6 to 30, more preferably 8 to 28, and even more preferably 10 to 24.
• Y2 represents —O— or —OCH 2 —.
• m represents an integer of 2 or more.
• m there are no particular limitations on m as long as it is 2 or more, but it is preferably 6 to 30, more preferably 8 to 28, and even more preferably 10 to 24.
• an example of the specific compound is a compound represented by general formula (S2).
• X 10 represents an amino group, a hydrazine group, a guanidine group, a phosphonic acid group, a sulfo group, or a carboxy group. Specific and preferred embodiments of each group represented by X 10 are as described above for the specific functional group. Among them, the group represented by X 10 is preferably a primary amino group, a phosphonic acid group, or a sulfo group. m represents an integer of 1 to 3, preferably 1 or 2, and more preferably 1.
• L 10 represents a (m+1)-valent linking group or a single bond.
• L 10 is preferably a (m+1)-valent linking group.
• the preferred range of m is as described above.
• the aliphatic hydrocarbon groups which may have at least one linking group are preferred.
• the aliphatic hydrocarbon group represented by L 10 is preferably a divalent or trivalent aliphatic hydrocarbon group which may have at least one linking group described above.
• the divalent aliphatic hydrocarbon group which may have at least one linking group includes a divalent aliphatic hydrocarbon group, --O--.
• Examples of the trivalent aliphatic hydrocarbon group which may have at least one linking group include -O-divalent aliphatic hydrocarbon groups -N(-divalent aliphatic hydrocarbon group) 2 , -N(-divalent aliphatic hydrocarbon group) 2 , and trivalent aliphatic hydrocarbon groups.
• the "divalent aliphatic hydrocarbon groups" may be the same or different.
• the aliphatic hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 2 to 18 carbon atoms, and even more preferably 6 to 18 carbon atoms.
• the aliphatic hydrocarbon group is preferably an alkylene group.
• the aromatic ring group represented by L10 is preferably a divalent or trivalent aromatic ring group.
• An example of the divalent aromatic ring group is a phenylene group.
• An example of the trivalent aromatic ring group is a group obtained by removing three hydrogen atoms from a benzene ring.
• M represents an integer of 2 or more, preferably 2 to 4, more preferably 2 or 3, and still more preferably 2.
• a plurality of X 10 's, a plurality of L 10 's, and a plurality of m's may be the same or different, but are often the same.
• Ar 10 represents an aromatic ring group having a valence of (M+t).
• Ar 10 is preferably a group obtained by removing (M+t) hydrogen atoms from benzene, biphenyl, or naphthalene, and more preferably a group represented by any one of the formulae (5-1) to (5-3) described later.
• Y 10 represents an ethylenically unsaturated group.
• examples of the ethylenically unsaturated group represented by Y 10 include those exemplified as the polymerizable group above, and among these, a vinyl group, a styryl group, or an acrylamide group is preferred.
• t represents 1 or 2, and is preferably 1.
• a plurality of Y 10 may be the same or different, but are often the same.
• the specific compound When the specific compound has two or more specific functional groups, the specific compound is preferably a compound represented by general formula (4), and more preferably a compound represented by general formula (5) described below.
• X2 represents a primary amino group, a phosphonic acid group, or a sulfo group.
• L2 represents an alkylene group which may have an etheric oxygen atom.
• the alkylene group is preferably a linear alkylene group.
• the number of carbon atoms of the alkylene group which may have an etheric oxygen atom represented by L2 is preferably 1 to 20, more preferably 2 to 18, and even more preferably 6 to 18.
• p1 represents an integer of 2 or more, preferably 2 to 4, more preferably 2 or 3, and even more preferably 2.
• p2 represents 1 or 2, with 1 being preferred.
• Ar2 represents a (p1+p2)-valent aromatic ring group.
• the (p1+p2)-valent aromatic ring group represented by Ar2 is preferably a group obtained by removing (p1+p2) hydrogen atoms from an aromatic hydrocarbon.
• the aromatic hydrocarbon is preferably benzene, biphenyl or naphthalene.
• Ar 2 is more preferably a group represented by any one of the following formulae (5-1) to (5-3).
• X3 represents a primary amino group or a phosphonic acid group.
• L3 represents --(CH 2 ) r O-- or an alkylene group having 6 to 18 carbon atoms.
• r represents an integer of 2 to 18.
• r may be an integer of 2 to 18, preferably 6 to 18, and more preferably 8 to 12.
• Ar3 represents a group obtained by removing (q+1) hydrogen atoms from an aromatic hydrocarbon selected from the group consisting of benzene, biphenyl, and naphthalene, where q represents an integer of 2 or more, preferably 2 to 4, more preferably 2 or 3, and even more preferably 2.
• Ar 3 is preferably a group represented by any one of the above formulas (5-1) to (5-3).
• the molecular weight of the specific compound is not particularly limited, but is preferably 200 to 1000, more preferably 250 to 900, even more preferably 300 to 800, and particularly preferably 350 to 700.
• the content of the specific compound is preferably 10.00% by mass or less, more preferably 3.00% by mass or less, and even more preferably 1.00% by mass or less, based on the total mass of the composition.
• the lower limit is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, even more preferably 0.01% by mass or more, and particularly preferably 0.05% by mass or more.
• Two or more of the specific compounds may be used in combination. When two or more specific compounds are used in combination, the total content thereof is preferably within the above range.
• the composition comprises a solvent.
• Solvents include water and organic solvents.
• organic solvent include hydrocarbon solvents, alcohol solvents, polyol solvents, glycol ether solvents, ether solvents, ketone solvents, amide solvents, sulfur-containing solvents, and ester solvents.
• Hydrocarbon solvents include aliphatic hydrocarbon solvents such as n-pentane and n-hexane; alicyclic hydrocarbon solvents such as cyclohexane and methylcyclohexane; and aromatic hydrocarbon solvents such as toluene and xylene.
• the alcohol-based solvent examples include aliphatic alcohol-based solvents having 1 to 18 carbon atoms, such as methanol, ethanol, 1-propanol, 2-propanol (also referred to as isopropyl alcohol (IPA)), 2-butanol, isobutyl alcohol, tert-butyl alcohol, isopentyl alcohol, and 4-methyl-2-pentanol (also referred to as methyl isobutyl carbinol (MIBC)); alicyclic alcohol-based solvents having 3 to 18 carbon atoms, such as cyclohexanol; aromatic alcohol-based solvents, such as benzyl alcohol; and ketone alcohol-based solvents, such as diacetone alcohol.
• the alcohol solvent preferably has 1 to 8 carbon atoms, more preferably 2 to 7 carbon atoms, and even more preferably 3 to 6 carbon atoms.
• polyol-based solvents examples include glycol-based solvents having 2 to 18 carbon atoms.
• Glycol solvents include ethylene glycol, propylene glycol (1,2-propanediol), 1,3-propanediol, diethylene glycol, and dipropylene glycol.
• glycol ether solvents include glycol monoether solvents having 3 to 19 carbon atoms.
• glycol monoether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl ether, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 1-ethoxy-2-propanol, 2-ethoxy-1-propanol, propylene glycol monomethyl ether, propylene glycol mono-n-propyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropy
• Ketone solvents include, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
• ether solvents include diethyl ether, diisopropyl ether, dibutyl ether, t-butyl methyl ether, cyclohexyl methyl ether, and tetrahydrofuran.
• amide solvents include formamide, monomethylformamide, dimethylformamide, acetamide, monomethylacetamide, dimethylacetamide, monoethylacetamide, diethylacetamide, and N-methylpyrrolidone.
• sulfur-containing solvents examples include dimethyl sulfone, dimethyl sulfoxide, and sulfolane.
• ester solvents include n-butyl acetate, ethyl lactate, propylene glycol acetate, propylene glycol monomethyl ether acetate, gamma-butyrolactone, and delta-valerolactone.
• the solvent is preferably an organic solvent, and more preferably a glycol monoether solvent or an alcohol solvent.
• the content of the solvent in the present composition is preferably from 90.00 to 99.9999 mass %, more preferably from 97.00 to 99.999 mass %, and even more preferably from 99.00 to 99.99 mass %, based on the total mass of the composition.
• the total amount of the specific compound and the solvent is preferably 95.00% by mass or more, more preferably 99.00% by mass or more, and even more preferably 99.90% by mass or more, based on the total mass of the composition.
• the upper limit is not particularly limited, and may be, for example, 100% by mass or less.
• the total amount of the specific compound and the solvent is within the above range, the amount of components other than the specific compound and the solvent is very small, so that the composition contains few impurities and can efficiently form a film consisting of the specific compound on a substrate.
• Two or more kinds of solvents may be used in combination. When two or more kinds of solvents are used in combination, the total content thereof is preferably within the above range.
• the present composition preferably contains a polymerization inhibitor.
• the polymerization inhibitor is not particularly limited, and a known polymerization inhibitor may be selected depending on the type of crosslinkable group (polymerizable group) possessed by the specific compound, but a radical polymerization inhibitor is preferable.
• the polymerization inhibitor preferably contains at least one compound selected from the group consisting of phenolic compounds, quinone compounds, free radical compounds, amine compounds, and phosphine compounds, and from the viewpoint of polymerization inhibition ability, free radical compounds are more preferable.
• phenolic compounds include 4-methoxyphenol, hydroquinone, 2-tert-butylhydroquinone, 4-tert-butylcatechol, pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,5-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-methylphenol, 4,4'-thiobis(3-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 4-methoxynaphthol, 2,4-bis(octylthiomethyl)-6-methylphenol, p-nitrosophenol, and ⁇ -nitroso- ⁇ -naphthol.
• the quinone compounds include 1,4-benzoquinone, 1,2-benzoquinone, and 1,4-naphthoquinone.
• Free radical compounds include poly(4-methacryloyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl), 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, 2,2,6,6-tetramethylpiperidine 1-oxyl, 2,2-diphenyl-1-picrylhydrazyl, and triphenylphenyldazyl.
• amine compounds include p-phenylenediamine, 4-aminodiphenylamine, N,N-diethylhydroxylamine, N,N'-diphenyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N,N'-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl- ⁇ -naphthylamine, 4,4'-dicumyl-diphenylamine, 4,4'-dioctyl-diphenylamine, phenothiazine, 2-methoxyphenothiazine, phenoxazine, N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodina
• Each of the compounds exemplified as the amine-based compound may form a metal salt or a metal complex.
• An example of the phosphine-based compound is tris(2,4-di-tert-butylphenyl)phosphite.
• polymerization inhibitors may include nitrobenzene-based compounds such as nitrobenzene and 4-nitrotoluene, as well as thiol ethers such as dioctadecyl 3,3'-thiodipropionate, dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate.
• nitrobenzene-based compounds such as nitrobenzene and 4-nitrotoluene
• thiol ethers such as dioctadecyl 3,3'-thiodipropionate, dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate.
• the molecular weight of the polymerization inhibitor is preferably 1,000 or less, more preferably 800 or less, and even more preferably 500 or less. There is no particular lower limit to the molecular weight, but it is preferably 80 or more.
• the content of the polymerization inhibitor is preferably 0.0001 parts by mass or more, more preferably 0.001 parts by mass or more, still more preferably 0.005 parts by mass or more, and particularly preferably 0.010 parts by mass or more, per 100 parts by mass of the specific compound.
• the content of the polymerization inhibitor is preferably 10.0 parts by mass or less, more preferably 1.000 parts by mass or less, and even more preferably 0.100 parts by mass or less, relative to 100 parts by mass of the content of the specific compound.
• the present composition may contain one type of polymerization inhibitor alone or two or more types. When two or more types of polymerization inhibitors are contained, the total amount thereof is preferably within the above range.
• the composition can be produced by mixing the above-mentioned components.
• the order or timing of mixing the components in the composition is not particularly limited.
• the composition may be produced by adding a specific compound to a stirrer such as a mixer containing a purified solvent, and then thoroughly stirring the mixture.
• the composition may be produced by adding other components in addition to the specific compound, the other components may be added simultaneously with the specific compound or at different times.
• the steps described below may be carried out.
• the above production method may include a metal removal step of removing metal components from the above components and/or compositions (hereinafter also referred to as "material to be purified").
• the above-mentioned production method preferably includes a filtration step of filtering the liquid in order to remove foreign matter, coarse particles, and the like from the liquid.
• the filtration method is not particularly limited, and any known filtration method can be used. Among them, filtering using a filter is preferred.
• the method for producing the composition may further include a static elimination step of eliminating static electricity from the composition.
• the present composition is a composition for semiconductor device processing.
• for semiconductor device processing means that it is used in the manufacture of a semiconductor device.
• the present composition can be used in any process for manufacturing a semiconductor device, for example, in the process of treating a semiconductor substrate included in the method of manufacturing a semiconductor device. More specifically, the present composition is preferably used in a method for producing a modified substrate, which will be described in detail later.
• the present composition can be used in the process of treating a semiconductor substrate, and the present composition can typically be used by contacting a workpiece containing metal atoms (particularly, a substrate having a surface containing metal atoms).
• the workpiece may contain multiple types of metal atoms.
• the contact angle of the film obtained by applying the composition to water is preferably 60 degrees or more, more preferably 90 degrees or more, and even more preferably 105 degrees or more. There is no particular upper limit, and in many cases it is 120 degrees or less.
• the contact angle of the film obtained by applying the present composition to water can be measured, for example, by using a fully automatic contact angle meter DMo-901 (manufactured by Kyowa Interface Science Co., Ltd.).
• the substrate in the method for treating a substrate using the composition is not particularly limited, but preferably has at least two surfaces, a first surface and a second surface, which are made of different materials.
• a specific compound can be selectively bonded or adsorbed to one of the surfaces to form a coating that is highly inhibitory to ALD coating formation on the other surface. It is preferred that by treating a substrate having at least two surfaces, a first surface and a second surface, with the composition, a coating that is highly inhibitory to ALD film formation is formed on the first surface, and a coating by the ALD process is selectively formed on the second surface.
• the material constituting the first surface and the material constituting the second surface are not particularly limited as long as they are different from each other, and may be either an organic material or an inorganic material. In terms of better effects of the present invention, however, it is preferable that at least one of the first surface and the second surface contains metal atoms, and it is more preferable that the first surface contains metal atoms.
• metalloid atoms such as boron, silicon, germanium, arsenic, antimony, and tellurium are also included in the metal atoms.
• the metal atom may be, for example, a metal (e.g., a simple metal) or a metal atom contained in a compound.
• the metal atom may also be a metal atom contained in a pure metal or an alloy.
• the metal atom is preferably a transition metal atom, more preferably at least one metal atom selected from the group consisting of a copper atom, a cobalt atom, a titanium atom, a tantalum atom, a tungsten atom, a ruthenium atom, and a molybdenum atom, more preferably at least one metal atom selected from the group consisting of a titanium atom, a tungsten atom, a ruthenium atom, and a molybdenum atom, and even more preferably a ruthenium atom or a tungsten atom.
• first surface and the second surface is an aspect in which one of the first surface and the second surface is a metallic surface made of a metal, and the other is a non-metallic surface made of a non-metal (hereinafter also referred to as aspect A).
• first surface is a metal surface and the second surface is a non-metal surface.
• Metals include pure metals or alloys.
• Non-metals include metal carbides, metal oxides, metal nitrides, metal oxynitrides, and organic materials.
• the pure metals and alloys are preferably composed of the preferred metal atoms exemplified above.
• metal carbides, metal oxides, metal nitrides, and metal oxynitrides are preferably metal carbides, metal oxides, metal nitrides, and metal oxynitrides of the preferred metal atoms exemplified above.
• first surface and the second surface is an embodiment in which the first surface is a surface composed of a material selected from the group consisting of a metal (pure metal or alloy), a metal carbide, a metal oxide, a metal nitride, and a metal oxynitride, and the second surface is composed of a material of a different type from the first surface and is a surface composed of a material selected from the group consisting of a metal (pure metal or alloy), a metal carbide, a metal oxide, a metal nitride, and a metal oxynitride (hereinafter also referred to as embodiment B).
• the first surface and the second surface being composed of different types of materials means that two types of materials are selected for the first surface and the second surface out of five types of materials: metal, metal carbide, metal oxide, metal nitride, and metal oxynitride.
• modes B include a mode in which the first surface is a metal surface composed of a metal, and the second surface is a metal oxide surface composed of a metal oxide (hereinafter also referred to as mode B1), a mode in which the first surface is a metal nitride surface composed of a metal nitride, and the second surface is a metal oxide surface composed of a metal oxide (hereinafter also referred to as mode B2), and a mode in which the first surface is a metal oxide surface composed of a metal oxide, and the second surface is a metal surface composed of a metal (hereinafter also referred to as mode B3).
• metals include copper, cobalt, titanium, tantalum, tungsten, ruthenium, and molybdenum.
• Metal oxides include silicon oxide and tetraethyl orthosilicate (TEOS).
• the metal nitride includes titanium nitride.
• Metal oxides include silicon oxide and tetraethyl orthosilicate (TEOS).
• the metal oxide includes silicon oxide and tetraethyl orthosilicate (TEOS).
• Metals include silicon.
• a suitable example of a method for treating a substrate is a method for producing a modified substrate using the present composition and a substrate having at least two surfaces, a first surface and a second surface, which are made of different materials.
• the method for producing a modified substrate preferably includes steps 1 to 3, and may include step 4 as necessary.
• Step 1 A step of contacting a substrate having at least two surfaces, a first surface and a second surface, which are made of different materials, with the composition to form a first film on the first surface.
• Step 2 A step of subjecting the substrate obtained in step 1 to atomic layer deposition (ALD) processing to form a second film on the second surface.
• Step 4 A step of heating the modified substrate obtained in step 3.
• Step 1 is a step of contacting a substrate having at least two surfaces, a first surface and a second surface, which are made of different materials (hereinafter, also simply referred to as a "specific substrate") with the present composition to form a first film on the first surface.
• the first film is a film containing a specific compound.
• the method of contacting the specific substrate with the composition is not particularly limited, and examples thereof include a method of applying or spraying the composition onto the specific substrate, and a method of immersing the specific substrate in the composition.
• the method of applying the composition onto the specific substrate is not particularly limited, and a known method can be used, and examples thereof include a spin coating method.
• the composition may be caused to circulate.
• the temperature of the composition when it is brought into contact with the specific substrate is not particularly limited, but is preferably 0 to 50°C, more preferably 10 to 30°C.
• the rinse treatment can remove the specific compound adhering to areas other than the desired area on the specific substrate from the specific substrate.
• the rinsing method is not particularly limited, but may be a method of contacting the specific substrate with a rinsing liquid.
• the contacting method may be the same as the method of contacting the composition with the specific substrate.
• the temperature of the rinsing liquid during contact is not particularly limited, but is preferably 0 to 50°C, more preferably 10 to 30°C.
• the rinse liquid is not particularly limited, and may be the solvent contained in the present composition. The same type of solvent as that contained in the present composition may be used as the rinse liquid.
• Step 2 is a step of subjecting the specific substrate (specific substrate having the first film) obtained in step 1 to an atomic layer deposition process (ALD process) to form a second film on the second surface.
• ALD process atomic layer deposition process
• the reaction of the polymerizable groups of the specific compound in the first film progresses and the first film is hardened, and the formation of the second film is inhibited by the hardened first film, so that a modified substrate is obtained in which the second film (ALD coating) is formed with high selectivity on the region (second surface) where the first film is not formed.
• the materials used to form Langmuir-Blodgett films and self-assembled monolayers are often low molecular weight materials. Compared with polymeric materials, these materials are very effective in selectively forming modified films in minute regions on a substrate. However, these materials often have poor resistance to the heating of the substrate during ALD processing. In contrast, in process 2, although the specific compound is a low molecular weight material, it has a polymerizable group, and therefore, as described above, when the substrate is heated in the ALD process, the first film becomes a hardened film and is able to exhibit sufficient heat resistance, making it possible to inhibit the formation of an ALD coating in a fine area while maintaining heat resistance.
• a precursor serving as a raw material for the second film is supplied to the surface of the specific substrate obtained in step 1.
• the material constituting the second film can be controlled by the type of precursor supplied, the supply atmosphere, the oxidizing agent, etc.
• the second film formed by the ALD process is not particularly limited, but is preferably a metal film, a metal oxide film, or a metal nitride film, and more preferably a metal film or a metal oxide film.
• metals that may form the metal film include aluminum, titanium, chromium, iron, cobalt, nickel, copper, zinc, yttrium, zirconium, niobium, molybdenum, ruthenium, palladium, lanthanum, cerium, hafnium, tantalum, tungsten, platinum, and bismuth.
• metal oxides constituting the metal oxide film include aluminum oxide, titanium oxide, zinc oxide, zirconium oxide, hafnium oxide, and tantalum oxide.
• the metal nitride constituting the metal nitride film include titanium nitride and tantalum nitride. In the ALD process, a process for modifying the surface of the region where the first film is not formed may be performed.
• the ALD process is not particularly limited, but is preferably a thermal ALD process.
• the substrate heating temperature in the ALD treatment is preferably 100 to 400°C, more preferably 150 to 400°C, and even more preferably 200 to 300°C.
• the difference between the thickness of the second film on the second surface and the thickness of the second film on the region where the first film is formed is preferably 1.0 nm or more, more preferably 1.2 nm or more, and even more preferably 1.5 nm or more.
• the upper limit of the thickness difference is not particularly limited, but may be, for example, 100 nm or less.
• the method for producing a modified substrate may include, after step 2, step 3 of removing the first film formed on the specific substrate in step 1. By carrying out step 3 after step 2, a modified substrate having the second film formed only on the second surface can be obtained.
• the method for removing the first film is not particularly limited, but examples thereof include dry etching, wet etching, and a combination thereof. Dry etching may be a method of supplying reactive ions or reactive radicals to the surface of the modified substrate having the first film.
• the reactive ions or reactive radicals may be generated by plasma or the like, and are preferably generated by using a mixed gas containing one or more gases selected from the group consisting of oxygen, nitrogen, and hydrogen.
• the mixed gas may contain a rare gas.
• Dry etching may also be physical etching using a sputtering phenomenon.
• an etching solution may be supplied to the surface of the modified substrate having the first film.
• the etching solution include an etching solution containing an oxidizing agent such as ozone, and an etching solution containing an organic solvent.
• the organic solvent of the etching solution containing an organic solvent include the organic solvents contained in the above composition, and a hydrocarbon solvent is preferable.
• the method for producing a modified substrate may include step 4 of heating the modified substrate. Step 4 is preferably performed before step 2. By performing step 4, the polymerizable groups can react with each other.
• the heating temperature is not particularly limited, but is preferably from 100 to 400°C, more preferably from 150 to 400°C, and even more preferably from 200 to 300°C.
• the heating method is not particularly limited, and examples thereof include a method of contacting the substrate with a heating element (for example, heating with a hot plate) and a method of irradiating the substrate with infrared rays.
• the present invention also includes the invention of a compound.
• the compound of the present invention is a compound represented by the above general formula (2), a compound represented by the above general formula (3), and a compound represented by the above general formula (5).
• E-1 to E-22 used in each example E-1, E-4, E-6, E-8, E-9, E-10, E-11, E-12, E-14, and E-21 were synthesized with reference to any of the methods of Synthesis Examples 1 to 5 below.
• E-23 to E-35 used in each example E-25, E-26, E-30, E-31, and E-32 were synthesized with reference to any of the methods of Synthesis Examples 6 and 7 below.
• specific compounds other than those mentioned above commercially available products or synthetic products obtained according to known procedures were used.
• a solution was prepared separately by dissolving bis(2-methoxyethyl) azodicarboxylate (DMEAD (registered trademark), 19.4 g, 0.08 mol, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in THF (110 mL).
• DMEAD bis(2-methoxyethyl) azodicarboxylate
• THF THF
• the above-obtained solution was added dropwise to the reaction solution over 2 hours while maintaining the internal temperature of the reaction solution at 5° C. or lower. After completion of the addition, the reaction solution was stirred at 25° C. for 1 hour. Next, the solvent was distilled off from the reaction solution under reduced pressure of 40 ° C.
• a solution was prepared separately by dissolving bis(2-methoxyethyl) azodicarboxylate (DMEAD (registered trademark), 52.7 g, 0.23 mol, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in THF (158 mL).
• DMEAD bis(2-methoxyethyl) azodicarboxylate
• THF 158 mL
• the above-obtained solution was added dropwise to the reaction solution over 2 hours while maintaining the internal temperature of the reaction solution at 5° C. or lower.
• the reaction solution was stirred at 25° C. for 1 hour.
• the solvent was distilled off from the reaction solution under reduced pressure of 40 ° C.
• the solvent was distilled off from the obtained organic phase to obtain a 40% by mass ethyl acetate solution.
• Diisopropyl ether (260 mL, Fujifilm Wako Pure Chemical Industries, Ltd.) was added to the obtained 40% by mass ethyl acetate solution and cooled to 0 ° C. After stirring for 30 minutes at 0 ° C., crystals were precipitated and the crystals were filtered off.
• the obtained crystals and methanol (412 mL, manufactured by Mitsubishi Gas Chemical Co., Inc.) were added to a recovery flask and stirred for 1 hour at 25° C. The obtained crystals were filtered, washed with methanol, and then dried with air at 40° C. for 12 hours to obtain intermediate E-21A.
• reaction solution was cooled to 25°C, insoluble matter was removed by filtration, and the solvent was removed from the obtained filtrate under reduced pressure of 50°C/10 hPa. Thereafter, ethyl acetate (228 mL, Fujifilm Wako Pure Chemical Industries, Ltd.) was added and stirred at 25°C for 0.5 hours. The crystals were filtered off, washed with diisopropyl ether, and then dried with air at 40°C for 12 hours to obtain intermediate E-25A.
• compositions used in the examples and comparative examples were prepared by mixing the components in the proportions shown in the tables below.
• the preparation, filling, storage, etc. of the composition were all carried out in a clean room that satisfied ISO class 2 or lower.
• the containers used for the preparation, filling, storage, etc. of the composition were washed with the solvent used in the preparation or the prepared composition before use.
• a W-layer wafer was prepared as a substrate, in which a tungsten layer was formed by CVD (Chemical Vapor Deposition) on one surface of a commercially available silicon wafer (diameter 12 inches), and a Cu-layer wafer was prepared as a substrate, in which a copper layer was formed by sputtering.
• CVD Chemical Vapor Deposition
• a copper layer was formed by sputtering.
• the film formation conditions were adjusted so that the thicknesses of the W layer and the Cu layer were each 20 nm.
• the silicon wafer, and the W layer wafer and Cu layer wafer obtained by the above-described film formation were each cut into 2 cm squares, rinsed with isopropyl alcohol (IPA), and then dried by spraying nitrogen gas onto each wafer.
• the rinsing process was performed by immersing the substrate in IPA. The immersion was performed while stirring the IPA in a container with a magnetic stirrer at 250 rpm, the IPA temperature was 25° C., and the immersion time was 30 seconds.
• each wafer after the rinsing process was immersed in each composition.
• the immersion of each wafer in the composition was performed while stirring the composition in a container with a magnetic stirrer at 250 rpm, the temperature of the composition was 25° C., and the immersion time was 10 minutes.
• each wafer was rinsed with IPA in the same manner as above, and then dried with nitrogen gas to obtain a sample (evaluation sample) on which a film was formed by applying the composition to each wafer.
• ALD Inhibition Al 2 O 3 Deposition Inhibition and TaN Deposition Inhibition
• the ALD processing temperature was 200°C, trimethylaluminum was used as the organometallic raw material, and water was used as the oxidizing agent.
• the ALD processing temperature was 300°C, PDMAT (pentakis(dimethylamino)tantalum) was used as the organometallic raw material, and ammonia was used as the reducing agent.
• the ALD treatment of each sample was performed under conditions in which the film thickness was 5 nm for each sample (untreated sample) in which a coating film made of a specific compound was not formed.
• the thickness of the ALD coating on the sample after the ALD process was measured using an X-ray fluorescence (XRF) analyzer (AZX400 manufactured by Rigaku Corporation). The thickness of the ALD coating was measured at five points on the sample, and the average value was taken as the thickness.
• the thickness (nm) of the ALD coating in the evaluation sample was evaluated according to the following evaluation criteria. The smaller the thickness (nm) of the ALD coating in the evaluation sample, the more difficult it is for a coating to be deposited by the ALD process, and the better the inhibition of deposition of the aluminum oxide layer or tantalum nitride layer.
• the thickness of the ALD film is less than 1.0 nm.
• A The thickness of the ALD coating is 1.0 nm or more and less than 1.5 nm.
• B The thickness of the ALD coating is 1.5 nm or more and less than 2.0 nm.
• C The thickness of the ALD coating is 2.0 nm or more and less than 2.5 nm.
• D The thickness of the ALD coating is 2.5 nm or more and less than 3.0 nm.
• E The thickness of the ALD coating is 3.0 nm or more and less than 3.5 nm.
• F The thickness of the ALD film is 3.5 nm or more.
• Tables 1 to 3 and Tables 4 to 5 The components used in the preparation of the compositions and their content ratios (mass ratios) are shown in Tables 1 to 3 and Tables 4 to 5 described below. Furthermore, Tables 1, 2, and 4 show the evaluation results using W-layer wafers, and Tables 3 and 5 show the evaluation results using Cu-layer wafers. Tables 1 to 3 show the evaluation results of Al 2 O 3 deposition inhibition, and Tables 4 and 5 show the evaluation results of TaN deposition inhibition. In the table, the numerical value showing the content of each component means the content of each component (unit: "parts by mass") when the total mass of each composition is 100 parts by mass.
• the “balance” refers to an amount adjusted so that the total amount of the components other than the solvent (specific compound and polymerization inhibitor) contained in each composition and the solvent is 100 parts by mass.
• the column “Conjugate acid pKa” indicates the value of the acid dissociation constant of the conjugate acid of a specific compound.
• the “pKa” column indicates the value of the acid dissociation constant of a specific compound.
• the acid dissociation constant is a value calculated using the following software package 1 based on a database of Hammett's substituent constants and known literature values.
• Software package 1 Advanced Chemistry Development (ACD/Labs)
• E-1 to E-35 The structures of the specific compounds (E-1 to E-35) are shown below.
• E-1 to E-13, E-22, and E-23 to E-32 are specific compounds having a basic functional group as a specific functional group
• E-14 to E-21 and E-33 to E-35 are specific compounds having an acidic functional group as a specific functional group.
• ⁇ Polymerization inhibitor> A-1 4-Methoxyphenol A-2: 1,4-Benzoquinone A-3: Phenothiazine A-4: 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl A-5: 2,2-Diphenyl-1-picrylhydrazyl A-6: 2,2,6,6-tetramethylpiperidine 1-oxyl
• composition of the present invention can form a coating that has a high inhibitory effect on the formation of an ALD coating.
• the composition of the comparative example contained a compound having only a polymerizable group or a specific functional group, but did not contain the specific compound, and therefore did not have a sufficient effect on inhibiting the formation of an ALD film.
• Example A2 Furthermore, from a comparison between Example A2 and Example A4, it was confirmed that the effects of the present invention are more excellent when the specific functional group in the specific compound is an amino group, a hydrazine group, or a guanidine group. From a comparison between Example A3 and Example A5, it was confirmed that the effects of the present invention are superior when the specific functional group in the specific compound is a primary amino group, a secondary amino group, or a tertiary amino group. Comparison between Example A5 and Example A7 and the like confirmed that the effects of the present invention are superior when the specific functional group in the specific compound is a primary amino group.
• Example A7 and A13 with Example A17, etc. confirmed that the effects of the present invention are superior when the polymerizable group in the specific compound is an aromatic vinyl group, an acryloyloxy group, a methacryloyloxy group, an acrylamide group, a methacrylamide group, a maleimide group, or a vinyl ether group. From a comparison between Example A5 and Example A6, it was confirmed that the effects of the present invention are more excellent when the polymerizable group in the specific compound is a styryl group or a vinylnaphthyl group.
• Example A4 in Table 1 instead of using 0.10 parts by mass of Specific Compound E-4, 0.095 parts by mass of Specific Compound E-4 and 0.005 parts by mass of Comparative Compound CE-1 were used in combination, and the other conditions were the same as in Example A4 to evaluate the ALD inhibitory activity. It was confirmed that the same effect as in Example A4 was obtained.

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