JP7655735B2 - New conductivity enhancer - Google Patents

Description

The present disclosure relates to novel electrical conductivity enhancers and related technologies. More specifically, the present disclosure relates to compositions for improving the electrical conductivity of conductive materials, comprising a copolymer of compounds including an ether moiety-containing (meth)acrylic monomer component group, a halogen-containing (meth)acrylic monomer component group, and a hydroxyl-containing (meth)acrylic monomer component group, and optionally including a crosslinker.

Various improvements have been made to conductive materials and conductors. However, the conductive materials currently available are limited to those that contain a specific combination of conductive components.

JP 2019-102719 A International Publication No. 2015/099049 International Publication No. 2019/039511 International Publication No. 2017/163615 JP 2017-183207 A

The present disclosure provides a conductive material that includes a desired combination of conductive components that improves the electrical conductivity of the conductive material.

The present disclosure provides compositions or combinations, various methods of making and using the same, for improving the electrical conductivity of electrical conductors, for example, comprising A) at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, B) at least one compound from a group of halogen-containing (meth)acrylic monomer components, and C) at least one compound from a group of hydroxy-containing (meth)acrylic monomer components.

In the present disclosure, it is contemplated that one or more features described herein may be provided in combinations in addition to those combinations explicitly stated. Various embodiments and advantages of the present disclosure will be recognized by those skilled in the art upon reading and understanding the following detailed description, if necessary.

The present disclosure provides a conductivity enhancer, and by using the conductivity enhancer, a technology can be provided that can improve electrical conductivity. The present disclosure also improves electrical conductivity while improving flexibility. The present disclosure also produces a conductive material that has improved electrical conductivity and improved durability.

Hereinafter, the present disclosure will be described with reference to the best mode. Throughout this specification, the singular expression should be understood to include the concept of the plural form, unless otherwise specified. Therefore, the singular article (e.g., in the case of English, "a", "an", "the", etc.) should be understood to include the concept of the plural form, unless otherwise specified. In addition, it should be understood that the terms used in this specification are used in the sense commonly used in the field, unless otherwise specified. Therefore, unless otherwise defined, all technical terms and scientific and technical terms used in this specification have the same meaning as commonly understood by those skilled in the art to which this disclosure belongs. In the case of conflict, the present specification (including definitions) will take precedence.

The following provides definitions of terms and/or basic technical content that are particularly used in this specification.

(Definition of terms)
In this specification, the electrical conductivity (or resistivity) is measured as follows: Specifically, unless otherwise specified, a measurement object (e.g., a film or the like) is cut into a size of 0.5 cm length × 2.00 cm width × 0.2 cm thickness, and a value measured by a four-terminal measurement method (e.g., Loresta GP [manufactured by Mitsubishi Chemical Analytech Co., Ltd.] can be used, but is not limited to this) is used.

In this specification, the term "conductive material" refers to any material having electrical conductivity. In this specification, the conductive material refers to a material having a resistivity of 1.0×10 ^-1 Ω·cm or less, usually 1.0×10 ^-2 Ω·cm or less, preferably 1.0×10 ^-3 Ω·cm or less, but is not limited thereto. The conductive material contains a conductive component that imparts electrical conductivity. Typically, the conductive material is usually composed of a base material and a conductive component.

As used herein, "improving electrical conductivity" refers to a significant increase in electrical conductivity when the components of the present disclosure are added to a conductive component or conductive material, compared to when no components are added. For example, improving electrical conductivity by at least about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 99%, and can also be expressed in terms of a decrease in volume resistivity. For example, this means that the volume resistivity is reduced by about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 99% compared to the comparison target.

In this specification, the term "substrate", also referred to as the matrix, refers to the basic part of the structure of the conductive material, and corresponds to the base on which the conductive components are placed. Various polymers can be used as the substrate. When the substrate is a polymer, the substrate may be referred to as a polymer matrix.

In this specification, the term "conductive component" refers to any component that imparts electrical conductivity. Examples of conductive components include, but are not limited to, any metal component, metal-based components such as metal oxides and metal carbides, conductive carbon-based components, conductive organic compounds, conductive polymers, and the like.

In this specification, the term "metal-based component" refers to a component that contains metal atoms in some form as its constituent elements, and is a concept that includes metal components such as metals as well as components derived from metals (e.g., metal oxides, metal carbides, metal sulfides, etc.).

In this specification, "metal component" includes metals and alloys.

In this specification, "conductive carbon-based components" refers to conductive materials that contain carbon. Specific examples include, but are not limited to, natural graphite such as flake graphite, graphite such as artificial graphite, carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black, carbon-based materials such as graphene, carbon nanotubes, and fullerene, carbon fibers, and carbon fluorides. Metal carbides are not included in the conductive carbon-based components. "Conductive carbon-based components" may also be referred to as "carbon-based components."

In this specification, "(meth)acrylic monomer" refers to a monomer containing an acrylic group and/or a methacrylic group, and examples thereof include acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, acrylic acid amides, methacrylic acid amides, etc.

In this specification, "(meth)acrylic" means "acrylic" or "methacrylic", and "(meth)acrylate" means "acrylate" or "methacrylate".

In this specification, the term "ether moiety-containing (meth)acrylic monomer component group" refers to a collection of (meth)acrylic monomers containing at least one ether moiety. In this disclosure, one or more compounds of the ether moiety-containing (meth)acrylic monomer component group may be used. Examples of compounds of the ether moiety-containing (meth)acrylic monomer component group include tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, and (5-ethyl-1,3-dioxane-5-yl)methyl (meth)acrylate, but the present disclosure is not limited to only these examples. Compounds of the ether moiety-containing (meth)acrylic monomer component group of the present disclosure may be referred to herein as "ether moiety-containing (meth)acrylate".

In this specification, the term "halogen-containing (meth)acrylic monomer component group" refers to a collection of (meth)acrylic monomers containing at least one halogen. In this disclosure, one or more compounds of the halogen-containing (meth)acrylic monomer component group may be used. Examples of compounds of the halogen-containing (meth)acrylic monomer component group include 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, and 1H,1H,2H,2H-tridecafluorooctyl (meth)acrylate, but the present disclosure is not limited to these examples. Compounds of the halogen-containing (meth)acrylic monomer component group of this disclosure may be referred to as "halogen-containing (meth)acrylate" in this specification.

In this specification, the term "hydroxy-containing (meth)acrylic monomer component group" refers to a collection of (meth)acrylic monomers containing at least one hydroxy. The hydroxy-containing (meth)acrylic monomer component group may preferably contain a crosslinkable portion. In this disclosure, one or more compounds of the hydroxy-containing (meth)acrylic monomer component group may be used. Examples of compounds of the hydroxy-containing (meth)acrylic monomer component group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate, but the present disclosure is not limited to only these examples. Compounds of the hydroxy-containing (meth)acrylic monomer component group of this disclosure may be referred to as "hydroxy-containing (meth)acrylate" in this specification.

In this specification, the term "unsubstituted alkyl (meth)acrylic monomer component group" refers to a group of monomers containing a (meth)acrylic structure that does not have a substantial functional group (e.g., contains only an alkyl group). In the present disclosure, one or more compounds of the unsubstituted (meth)acrylic monomer component group may be used. Examples of compounds of the unsubstituted alkyl (meth)acrylic monomer component group include ethyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-octyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate, but the present disclosure is not limited to only these examples.

The composition or combination according to the present invention may be in the following forms.
(1) The compound of the ether moiety-containing (meth)acrylic monomer component group contains neither a halogen nor a hydroxy group, the compound of the halogen-containing (meth)acrylic monomer component group contains neither an ether moiety nor a hydroxy group, and the compound of the hydroxy-containing (meth)acrylic monomer component group contains neither an ether moiety nor a halogen.
(2) One of the two or more monomers contained in the composition or combination according to the present invention (a first monomer) corresponds to two of an ether moiety-containing (meth)acrylic monomer, a halogen-containing (meth)acrylic monomer, and a hydroxyl-containing (meth)acrylic monomer, and the other (a second monomer) is a monomer type that does not correspond to the first monomer.
(3) One of the three or more monomers contained in the composition or combination according to the present invention (first monomer) corresponds to two of the following: an ether moiety-containing (meth)acrylic monomer, a halogen-containing (meth)acrylic monomer, and a hydroxyl-containing (meth)acrylic monomer, another (second monomer) is a monomer species to which the first monomer does not belong, and another (third monomer) is the same as one of the monomer species to which the first monomer belongs. In this case, the first monomer is treated as a monomer species to which the third monomer does not belong.

In this specification, a "crosslinking agent" is a reactant that can react with functional groups on a polymer to link the polymers intramolecularly or intermolecularly. Examples of crosslinking agents include formaldehyde, 2,4-tolylene diisocyanate, hexamethylene diisocyanate, polyisocyanates (e.g., hexamethylene diisocyanate-based, etc.), Duranate ^™ (manufactured by Asahi Kasei Corporation), etc., but the present disclosure is not limited to only these examples.

In this specification, a "crosslinking functional group" refers to a functional group that can form a crosslinked structure, and the crosslinking functional group can react with a crosslinking agent to form an intermolecular or intramolecular crosslinked structure.

In this specification, the term "substitutable number" refers to the maximum number of hydrogen atoms that can be substituted when a hydrogen atom on a group is replaced with a substituent, provided that the resulting group is chemically stable.

In this specification, an alkyl group may be linear or branched. Examples of alkyl groups having 1 to 4 carbon atoms (C _1-4 alkyl) include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and sec-butyl groups. Examples of alkyl groups having 1 to 6 carbon atoms (C _1-6 alkyl) include, but are not limited to, C _1-4 alkyl, n-pentyl, isoamyl, n-hexyl, and isohexyl groups. Examples of alkyl groups having 1 to 10 carbon atoms (C _1-10 alkyl) include, but are not limited to, C _1-6 alkyl, n-octyl, n-nonyl, isononyl, branched nonyl, n-decanyl, and isodecyl groups. Examples of alkyl groups having 1 to 18 carbon atoms (C _1-18 alkyl groups) include C _1-10 alkyl groups, undecyl groups, lauryl groups, tridecyl groups, myristyl groups, pentadecyl groups, palmityl groups, heptadecyl groups, stearyl groups, and isostearyl groups, but the present disclosure is not limited to only these examples.

In this specification, an alkenyl group may be linear or branched. Examples of alkenyl groups having 2 to 6 carbon atoms include, but are not limited to, ethenyl, 1-propenyl, 2-propenyl, butenyl, pentenyl, and hexenyl groups. Examples of alkenyl groups having 2 to 10 carbon atoms include, but are not limited to, alkenyl groups having 2 to 6 carbon atoms, heptenyl, octenyl, nonenyl, and decenyl groups.

In this specification, examples of alkoxy groups having 1 to 6 carbon atoms include methoxy groups, ethoxy groups, n-propyloxy groups, isopropyloxy groups, n-butyloxy groups, isobutyloxy groups, tert-butyloxy groups, sec-butyloxy groups, n-pentyloxy groups, isoamyloxy groups, n-hexyloxy groups, and isohexyloxy groups, but the present disclosure is not limited to these examples.

As used herein, the term "alkoxy-substituted alkyl group" refers to an alkyl group in which one or more hydrogen atoms on the alkyl group are substituted with an alkoxy group.

As used herein, the term "haloalkyl group" refers to an alkyl group in which one or more hydrogen atoms on the alkyl group are replaced with halogen atoms. Also, the term "perhaloalkyl" refers to an alkyl group in which all hydrogen atoms on the alkyl group are replaced with halogen atoms. Examples of haloalkyl groups having 1 to 6 carbon atoms (C _1-6 haloalkyl groups) include C _1-6 fluorinated alkyl groups, such as a trifluoromethyl group, a trifluoroethyl group (such as a 2,2,2-trifluoroethyl group), a perfluoroethyl group, a trifluoro n-propyl group, a tetrafluoropropyl group (such as a 2,2,3,3-tetrafluoropropyl group), a perfluoro n-propyl group, a trifluoroisopropyl group, a perfluoroisopropyl group, a trifluoro n-butyl group, a perfluoro n-butyl group, a trifluoroisobutyl group, a perfluoroisobutyl group, a trifluoro tert-butyl group, a perfluoro tert-butyl group, a trifluoro n-pentyl group, an octafluoropentyl group (such as a 2,2,3,3,4,4,5,5-octafluoropentyl group), a perfluoro n-pentyl group, a trifluoro n-hexyl group, and a perfluoro n-hexyl group, but the present disclosure is not limited to only these examples. Examples of haloalkyl groups having 1 to 8 carbon atoms (C _1-8 haloalkyl groups) include C _1-6 haloalkyl groups or C _1-8 fluorinated alkyl groups, such as undecafluoro n-heptyl groups, perfluoro n-heptyl groups, tridecafluorooctyl groups (such as 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl groups), perfluoro n-octyl groups, and the like, but the present disclosure is not limited to only these examples.

In the present specification, the term "cycloalkyl group" refers to a monocyclic or polycyclic saturated hydrocarbon group, and includes those with a bridged structure. For example, "C _3-12 cycloalkyl group" refers to a cyclic alkyl group having 3 to 12 carbon atoms. Specific examples of C _6-12 cycloalkyl groups include cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, isobornyl group, 2-methyl-2-adamantyl group, 2-ethyl-2-adamantyl group, and the like, but the present disclosure is not limited to only these examples. Specific examples of C _5-12 cycloalkyl groups include cyclopentyl group, C _6-12 cycloalkyl group, and the like, but the present disclosure is not limited to only these examples. Specific examples of C _3-12 cycloalkyl groups include cyclopropyl group, cyclobutyl group, C _5-12 cycloalkyl group, and the like. Preferably, "C _6-12 cycloalkyl group" is included, but the present disclosure is not limited to only these examples.

In the present specification, the term "cycloalkenyl group" refers to a monocyclic or polycyclic unsaturated hydrocarbon group containing a double bond, and also includes those with a crosslinked structure. Examples include those in which one or more of the carbon-carbon bonds of the above-mentioned "cycloalkyl group" are double bonds. For example, a "C _3-12 cycloalkenyl group" refers to a cyclic alkenyl group having 3 to 12 carbon atoms. Specific examples of the "C _6-12 cycloalkenyl group" include a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, and a cyclononenyl group. Examples of the "C _3-12 cycloalkyl group" include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a C _6-12 cycloalkenyl group. Preferably, a "C _6-12 cycloalkenyl group" is mentioned, but the present disclosure is not limited to only such examples.

In this specification, "non-aryl heterocycloalkyl" and "non-aryl heterocycle" refer to a cyclic group having 1 to 3 atoms of the same or different types selected from nitrogen atoms, oxygen atoms, and sulfur atoms in the ring, and the group may contain one or more unsaturated bonds, but does not contain an aromatic group. For example, "3- to 8-membered non-aryl heterocycloalkyl" refers to a non-aryl heterocycloalkyl having 3 to 8 ring atoms. Specific examples of "non-aryl heterocycloalkyl" include oxiranyl group, oxetanyl group, pyranyl group, pyrrolidinyl group, imidazolidinyl group, piperidinyl group, morpholinyl group, thiomorpholinyl group, hexamethyleneiminyl group, thiazolidinyl group, tetrahydrofuranyl group, tetrahydropyridinyl group, tetrahydropyranyl group, 1,3-dioxolanyl group, 1,3-dioxanyl group, and 1,4-dioxanyl group, but the present disclosure is not limited to only these examples. The group also includes those with a crosslinked structure.

In this specification, "aryl group" refers to a group generated by removing one hydrogen atom bonded to an aromatic hydrocarbon ring. For example, a phenyl group (C ₆ H ₅ -) is derived from benzene, a tolyl group (CH ₃ C ₆ H ₄ -) is derived from toluene, a xylyl group ((CH ₃ ) ₂ C ₆ H ₃ -) is derived from xylene, and a naphthyl group (C ₁₀ H ₈ -) is derived from naphthalene. "C _6-14 aryl group" refers to an aromatic hydrocarbon group having 6 to 14 carbon atoms. Specific examples of "C _6-14 aryl group" include, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an azulenyl group, an acenaphthenyl group, an anthryl group, a fluorenyl group, a phenalenyl group, and a phenanthryl group. Specific examples of the "C _6-18 aryl group" include, for example, a C _6-14 aryl group, a benzo[a]anthryl group, a benzo[a]fluorenyl group, a benzo[c]phenanthryl group, a chrysenyl group, a fluoranthenyl group, a pyrenyl group, a tetracenyl group, and a triphenylenyl group. An arylthio group refers to an aryl-S- group. For example, a phenyl-S- group (phenylthio group) is included, but the present disclosure is not limited to only these examples.

In this specification, the term "heteroaryl group" refers to a monocyclic or polycyclic heteroatom-containing aromatic group, which contains one or more (e.g., 1 to 4) of the same or different heteroatoms selected from nitrogen, sulfur, and oxygen atoms. For example, a "5- to 18-membered heteroaryl group" refers to a heteroaryl group having 5 to 18 ring atoms. A "haloheteroaryl group" refers to a group in which one or more hydrogen atoms on the ring atoms are replaced with halogen. Specific examples of "heteroaryl groups" include, for example, pyrrolyl, thienyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, furyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, benzoisoxazolyl, benzoisothiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, and isoquinolyl. Examples of such groups include triazolyl groups, triazinyl groups, tetrazolyl groups, indolyl groups, imidazo[1,2-a]pyridyl groups, pyrazolo[1,5-a]pyridyl groups, [1,2,4]triazolo[1,5-a]pyridyl groups, benzimidazolyl groups, quinoxalyl groups, cinnolyl groups, quinazolyl groups, indazolyl groups, naphthyridyl groups, quinolinolyl groups, and isoquinolinolyl groups, but the present disclosure is not limited to these examples.

In this specification, "ether moiety-containing group" refers to a group having an oxygen atom between carbon atoms of an optionally substituted hydrocarbon group, and the group contains one or more (e.g., 1 to 4) oxygen atoms. Specific examples of "ether moiety-containing group" include, for example, methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, and ethoxybutyl group, but the present disclosure is not limited to only these examples.

In this specification, the term "halogen-containing group" refers to a group having a halogen atom in its partial structure, and the group contains one or more (e.g., 1 to 4) halogen atoms. Specific examples of "halogen-containing groups" include, for example, trifluoromethyl groups, trifluoroethyl groups, trifluoropropyl groups, trifluorobutyl groups, trichloromethyl groups, trichloroethyl groups, trichloropropyl groups, and trichlorobutyl groups, but the present disclosure is not limited to only these examples.

In this specification, the term "hydroxy-containing group" refers to a group that has a hydroxy group in its partial structure, and the group contains one or more hydroxy groups (e.g., 1 to 4). Specific examples of "hydroxy-containing groups" include, for example, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, and a hydroxybutyl group, but the present disclosure is not limited to only these examples.

In general, the term "substituted" refers to the replacement of one or more hydrogen radicals in a given structure with the radical of a particular substituent. It is recognized that the phrase "optionally substituted" is used interchangeably with the phrase "unsubstituted or substituted." For example, "a C _{6-18 aryl group optionally substituted with a C 1-10} alkyl group" is synonymous with "an unsubstituted C _6-18 aryl group, or a C _6-18 aryl group substituted with a C _1-10 alkyl group _. " In this specification, the number of substituents in a group defined using "substituted" or "optionally substituted" is not particularly limited as long as substitution is possible, and may be one or more. In addition, unless otherwise indicated, the description of each group also applies to the case where the group is a part or a substituent of another group. The number of carbon atoms in the definition of "substituent" may be expressed as, for example, "C _1-6 ". Specifically, the expression "C _1-6 alkyl" is synonymous with an alkyl group having 1 to 6 carbon atoms. In addition, in this specification, when a substituent is not specifically labeled with the term "substituted" or "optionally substituted", it means that the substituent is an "unsubstituted" substituent.

In this specification, "(meth)acrylate" means acrylate or methacrylate, and acrylate and methacrylate may be used alone or in combination. "(meth)acryloyloxy" means acryloyloxy or methacryloyloxy, and acryloyloxy and methacryloyloxy may be used alone or in combination. "(meth)acrylic acid" means acrylic acid or methacrylic acid, and acrylic acid and methacrylic acid may be used alone or in combination.

In this specification, the term "combination" refers to two or more compounds that are intended to be used together when used. The combination of compounds may be provided as one composition, but not all of the compounds in the combination may be included in one composition. They may be provided individually, or some may be provided in the same composition. For example, combinations of the first (meth)acrylate and the second (meth)acrylate described in this specification, combinations of the first (meth)acrylate, the second (meth)acrylate, and the third (meth)acrylate, and combinations of the second (meth)acrylate, the third (meth)acrylate, and the fourth (meth)acrylate, etc., are included, but the present disclosure is not limited to only such examples.

(Basic explanation of conductive materials)
The conductive material provided in the present disclosure includes any conductive component available in the art. The conductive material of the present disclosure is characterized in that it contains a composition for improving electrical conductivity (also called a conductivity improver) provided in the present disclosure, thereby improving electrical conductivity.

The conductive material of the present disclosure may typically contain a substrate other than the conductive component. The substrate material is not particularly limited, but if the substrate is intended to be peeled off, it is preferable that the substrate be made of a material that has releasability or that has been surface-treated.

(Basic explanation of electrical conductivity improver)
The composition for improving electrical conductivity (conductivity enhancer) or combination provided in the present disclosure, in one aspect, includes at least an "ether moiety-containing (meth)acrylic monomer", a "halogen-containing (meth)acrylic monomer", and a hydroxy-containing (meth)acrylic monomer. The composition may further include a crosslinker. The composition may further include an unsubstituted alkyl (meth)acrylic monomer, if desired.

により表され、含まれるエーテル含有基の種類、アルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In an exemplary embodiment, one example of a compound of the ether moiety-containing (meth)acrylic monomer component group provided in the present disclosure is represented by the formula (1):

and all of them improve electrical conductivity regardless of the type of ether-containing group contained therein, the form of the alkyl group (e.g., number of carbon atoms, branched or linear state), the form of the cycloalkyl group (e.g., number of carbon atoms), the form of the aryl group (e.g., number of carbon atoms), methacryloxy (R ¹ = methyl) or acryloxy (R ¹ = H), etc.

により表され、含まれるハロゲン含有基の種類、アルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In an exemplary embodiment, one example of a compound of the halogen-containing (meth)acrylic monomer component group provided in the present disclosure is represented by formula (2):

and all of them improve electrical conductivity regardless of the type of halogen-containing group contained therein, the form of the alkyl group (e.g., number of carbon atoms, branched or straight chain state), the form of the cycloalkyl group (e.g., number of carbon atoms), the form of the aryl group (e.g., number of carbon atoms), methacryloxy (R ¹ = methyl) or acryloxy (R ¹ = H), etc.

により表され、含まれるアルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In an exemplary embodiment, one example of a compound of the hydroxy-containing (meth)acrylic monomer component group provided in the present disclosure is represented by formula (3):

and all of these improve electrical conductivity regardless of the form of the alkyl group contained therein (e.g., number of carbon atoms, branched or straight chain state), the form of the cycloalkyl group (e.g., number of carbon atoms), the form of the aryl group (e.g., number of carbon atoms), methacryloxy (R ¹ = methyl), acryloxy (R ¹ = H), etc.

The basic method for using a conductivity enhancer is as follows:

(Conductive components targeted by the conductivity enhancer)
The conductive component that can be targeted by the conductivity improver of the present disclosure is any component having electrical conductivity.Preferably, metal-based components and conductive carbon-based components are included.More preferably, metal components, carbon black, graphene and carbon nanotubes are included.More preferably, silver and carbon nanotubes are included.

(General manufacturing method for conductive materials)
(1) Method for Producing Polymer Matrix In a representative embodiment, the polymer matrix of the present disclosure can be prepared by heating a monomer and/or by irradiating a monomer with ultraviolet light of a specific illuminance to polymerize the monomer. Such ultraviolet light irradiation can be carried out under conditions set by a person skilled in the art. When preparing a polymer matrix by polymerization using ultraviolet light, a complicated drying operation for removing the solvent is not required, and the workability is excellent.

The wavelength of the ultraviolet light used in this disclosure may be any wavelength within that range, and an appropriate wavelength may be selected depending on the purpose. For example, in this disclosure, any wavelength may be used as long as it can produce an initial effect on the monomer. Typically, it is a wavelength that can be irradiated by the light source used in the examples. Specifically, a light source of about 150 nm to 400 nm is used, and preferably 300 nm to 400 nm.

The preferred irradiance of the ultraviolet light used in this disclosure varies depending on the starting material. The ultraviolet light irradiation device is not particularly limited, and examples include low pressure mercury lamps, medium pressure mercury lamps, high pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, black light lamps, UV electrodeless lamps, short arc lamps, LEDs, etc.

When polymerizing the monomer, it is preferable to use a polymerization initiator. Examples of the polymerization initiator include a thermal polymerization initiator, a photopolymerization initiator, a redox polymerization initiator, an ATRP (atom transfer radical polymerization) initiator, an ICAR ATRP initiator, an ARGET ATRP initiator, a RAFT (reversible addition-fragmentation chain transfer polymerization) agent, an NMP (nitroxide-mediated polymerization) agent, and a polymer polymerization initiator. These polymerization initiators may be used alone or in combination of two or more types. Among these polymerization initiators, a photopolymerization initiator is preferable from the viewpoint of not leaving a thermal history in the polymer matrix.

Examples of photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,1'-biimidazole, 2,4,6-tris(trichloromethyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(p-methoxyphenylvinyl)-1,3,5-triazine, diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluorophosphate, 4,4'-ditert-butyldiphenylphosphine oxide ... phenyliodonium tetrafluoroborate, 4-diethylaminophenylbenzenediazonium hexafluorophosphate, benzoin, 2-hydroxy-2-methyl-1-phenylpropan-2-one, benzophenone, thioxanthone, 2,4,6-trimethylbenzoyldiphenylacylphosphine oxide, triphenylbutylborate tetraethylammonium, diphenyl-4-phenylthiophenylsulfonium hexafluorophosphate, 2,2-dimethoxy-1,2-diphenylethan-1-one, phenyl Photoradical polymerization initiators such as glyoxylic acid methyl ester, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 1,2-octanedione, 1-[4-(phenylthio)-2-(o-benzoyloxime)], bis(η5-2,4-cyclopentadiene-1-yl)bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyltitanium], 2,4,6-tris(trichloromethyl)-1,3 ,5-triazine, 2,4-bis(trichloromethyl)-6-(p-methoxyphenylvinyl)-1,3,5-triazine, diphenyliodonium tetrafluoroborate, 4,4'-ditert-butyldiphenyliodonium tetrafluoroborate, 4-diethylaminophenylbenzenediazonium hexafluorophosphate, diphenyl-4-phenylthiophenylsulfonium hexafluorophosphate, and other photocationic ring-opening polymerization initiators are included, but the present disclosure is not limited to these examples. These photopolymerization initiators may be used alone or in combination of two or more.

When a photopolymerization initiator is used as the polymerization initiator, the amount of the photopolymerization initiator is preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.

Examples of thermal polymerization initiators include azo-based polymerization initiators such as azobisisobutyronitrile (AIBN), 2,2'-azobis(methyl isobutyrate), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), and 1,1'-azobis(cyclohexane-1-carbonitrile), and peroxide-based polymerization initiators such as benzoyl peroxide, potassium persulfate, and ammonium persulfate, but the present disclosure is not limited to these examples. Each of these polymerization initiators may be used alone, or two or more types may be used in combination.

When a thermal polymerization initiator is used as the polymerization initiator, the amount of the thermal polymerization initiator is preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.

When a polymerization initiator that generates nitrogen (N ₂ ) during the polymerization reaction, such as AIBN, is used, the resulting composite may contain bubbles. Since such bubbles can be the starting point of breakage, it is expected that the properties of the composite, such as its extensibility, may be reduced, but the impact absorption ability may be improved. The bubbles contained in the composite are not limited to those derived from the polymerization initiator, and may be bubbles obtained by a known method that can include bubbles in a resin, such as those obtained by adding a foaming agent or removing a solvent.

Other polymerization initiators that can be used in the present disclosure include, for example, redox polymerization initiators such as hydrogen peroxide and iron (II) salts, persulfates and sodium hydrogen sulfite, ATRP (atom transfer radical polymerization) initiators using alkyl halides under a metal catalyst, ICAR ATRP initiators and ARGET ATRP initiators using metals and nitrogen-containing ligands, RAFT (reversible addition-fragmentation chain transfer polymerization) agents, NMP (nitroxide-mediated polymerization) agents, polymeric polymerization initiators such as polydimethylsiloxane unit-containing polymeric azo polymerization initiators, and polyethylene glycol unit-containing polymeric azo polymerization initiators, but the present disclosure is not limited to these examples. These polymerization initiators may be used alone or in combination of two or more types.

When polymerizing the monomer, a chain transfer agent may be used to adjust the molecular weight. The chain transfer agent can usually be used by mixing with the monomer. Examples of the chain transfer agent include α-methylstyrene dimer, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid, 2-(dodecylthiocarbonothioylthio)propionic acid, methyl 2-(dodecylthiocarbonothioylthio)-2-methylpropionate, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid 3-azido-1-propanol ester, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid pentafluorophenyl ester, mercaptan group-containing compounds such as lauryl mercaptan, dodecyl mercaptan, and thioglycerol, and inorganic salts such as sodium hypophosphite and sodium hydrogen sulfite, but the present disclosure is not limited to only these examples. These chain transfer agents may be used alone or in combination of two or more. The amount of the chain transfer agent is not particularly limited, but is usually about 0.01 parts by weight to about 10 parts by weight per 100 parts by weight of the total monomers.

The atmosphere in which the monomer is photopolymerized is not particularly limited, and may be air or an inert gas such as nitrogen gas or argon gas.

There are no particular limitations on the temperature at which the monomer is photopolymerized, and a temperature of about 5 to 100°C is usually preferred. The time required to polymerize the monomer varies depending on the polymerization conditions and cannot be determined in general, so it is arbitrary, but is usually about 1 to 20 hours.

The polymerization reaction can be terminated at any time when the amount of remaining monomer is 20% by mass or less. The amount of remaining monomer can be measured, for example, by gel permeation chromatography (GPC).

By polymerizing the monomer in this manner, a polymer matrix can be obtained.

In one embodiment, the monomers are polymerized in the absence of a crosslinking agent. In another embodiment, the monomers are polymerized in the presence of a crosslinking agent.

In one embodiment, the polymer matrix is thermally or photopolymerized. In another embodiment, the polymer matrix is thermally polymerized. In another embodiment, the polymer matrix is photopolymerized.

Methods for polymerizing monomers include, for example, bulk polymerization, solution polymerization, emulsion polymerization, and suspension polymerization, but the present disclosure is not limited to these examples. Among these polymerization methods, bulk polymerization and solution polymerization are preferred.

The polymerization of monomers can be carried out by, for example, radical polymerization, living radical polymerization, anionic polymerization, cationic polymerization, addition polymerization, polycondensation, catalytic polymerization, etc.

When polymerizing a monomer by solution polymerization, for example, the monomer can be polymerized by dissolving the monomer in a solvent and adding a polymerization initiator to the resulting solution while stirring the solution, or the monomer can be polymerized by dissolving a polymerization initiator in a solvent and adding the monomer to the resulting solution while stirring the solution. The solvent is preferably an organic solvent that is compatible with the monomer.

The copolymers included in the conductive materials of the present disclosure may be polymerized by using peroxide-based initiators (e.g., benzoyl peroxide, and azobisisobutyronitrile, and analogs thereof) as polymerization initiators.

When using the above-mentioned usable polymerization initiators as the polymerization initiator, the amount of the polymerization initiator is preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.

In one embodiment, electron beam polymerization is performed by irradiating the monomer with an electron beam. In one embodiment, the monomer can be polymerized by irradiation with an electron beam alone. In electron beam polymerization, the electron beam is irradiated in the presence of a photopolymerization initiator in one embodiment, and in the absence of a photopolymerization initiator in another embodiment. Both embodiments are within the scope of the present disclosure.

There are no particular limitations on the polymerization reaction temperature and atmosphere when thermally polymerizing the monomer. Typically, the polymerization reaction temperature is about 50°C to about 120°C. The atmosphere during the thermal polymerization reaction is preferably an inert gas atmosphere such as nitrogen gas. In addition, the thermal polymerization reaction time of the monomer varies depending on the polymerization reaction temperature, etc., so cannot be determined in general, but is usually about 3 to 20 hours.

(2) Method for producing the polymer matrix contained in the conductive material The polymer (or polymer matrix) contained in the conductive material of the present disclosure can be produced by mixing two or more specific monomers and polymerizing them under appropriate polymerization conditions, using an appropriate additive such as a polymerization initiator as necessary. The conductive material of the present disclosure can be produced by mixing the conductive component and any other components into this polymer matrix and heating it. The individual components and specific production conditions of the polymer are described in detail below.

In one aspect, the present disclosure relates to a method for producing a copolymer comprising at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, at least one compound from a group of halogen-containing (meth)acrylic monomer components, and at least one compound from a group of hydroxy-containing (meth)acrylic monomer components.

In another aspect, the present disclosure provides a method of making a conductive material comprising a copolymer described herein and a conductive component, the method comprising:
obtaining a copolymer by polymerizing at least one compound from the group of ether moiety-containing (meth)acrylic monomer components, at least one compound from the group of halogen-containing (meth)acrylic monomer components, and at least one compound from the group of hydroxy-containing (meth)acrylic monomer components;
The method includes mixing the copolymer and a conductive component to obtain a mixture, and heating the mixture to produce the conductive material.

によって表されるモノマーであり、式中、Ｒ^１は、水素原子またはメチル基であり、Ｒ^２は、アルキルオキシ、シクロアルキルオキシもしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールであり、
前記ハロゲン含有（メタ）アクリルモノマー成分群の少なくとも一種の化合物は、式（２）

によって表されるモノマーであり、式中、Ｒ^３は、水素原子またはメチル基であり、Ｒ^４は、１個から置換可能な数までの同一又は異なるハロゲン原子で置換されたアルキル、シクロアルキル、またはアリールであり、
前記ヒドロキシ含有（メタ）アクリルモノマー成分群の少なくとも一種の化合物は、式（３）

により表される、第三の（メタ）アクリレートであり、Ｒ^５は、水素原子またはメチル基であり、Ｒ^６は、ヒドロキシ基で置換されている、アルキル、シクロアルキル、またはアリールである。 In an exemplary embodiment, at least one compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1):

wherein R ¹ is a hydrogen atom or a methyl group, and R ² is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group;
At least one compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2)

wherein R ³ is a hydrogen atom or a methyl group, and R ⁴ is an alkyl, cycloalkyl, or aryl substituted with one to a substitutable number of the same or different halogen atoms;
At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3)

where R ⁵ is a hydrogen atom or a methyl group, and R ⁶ is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group.

One embodiment relates to a method for producing a copolymer comprising at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, at least one compound from a group of halogen-containing (meth)acrylic monomer components, and at least one compound from a group of hydroxyl-containing (meth)acrylic monomer components.

In one embodiment, a crosslinker is used in combination with at least one compound from the hydroxy-containing (meth)acrylic monomer component group.

One embodiment relates to a method for producing a copolymer comprising at least one compound from an ether moiety-containing (meth)acrylic monomer component group, at least one compound from a halogen-containing (meth)acrylic monomer component group, at least one compound from a hydroxy-containing (meth)acrylic monomer component group, and at least one compound from an unsubstituted alkyl (meth)acrylic monomer component group.

In one embodiment of the present disclosure, the polymerization of the monomers is carried out according to a polymerization method selected from the group consisting of bulk polymerization, solution polymerization, emulsion polymerization, and suspension polymerization. Without wishing to be bound by theory, the monomers of the present disclosure may be polymerized by chain polymerization, step-growth polymerization, or living polymerization.

(3-1) Method for Preparing Monomers The ether moiety-containing (meth)acrylic monomers, halogen-containing alkyl (meth)acrylates, hydroxy-containing alkyl (meth)acrylates, crosslinkers, unsubstituted alkyl (meth)acrylates and (meth)acrylic monomers used in the present disclosure may be commercially available from manufacturers such as those exemplified in the examples, or may be prepared according to methods well known to those skilled in the art.

(3-2) Production Method by Photopolymerization In one embodiment, the polymer matrix of the present disclosure is obtained in one step by photopolymerizing a monomer (including a plurality of types of monomers) in the presence of a polymerization initiator.
In one embodiment, the polymer matrix of the present disclosure can be prepared by irradiating an ether moiety-containing (meth)acrylic monomer, an alkyl (meth)acrylate substituted with a halogen group, and an alkyl (meth)acrylate substituted with a hydroxyl group with ultraviolet light in the presence of a polymerization initiator.
A preferred example of the polymerization initiator is 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
This step is usually carried out at room temperature for about 2 hours, but is not limited thereto, and may take 0.5 to 3 hours, or 0.5 to 24 hours or longer.

(3-3) Method for preparing a resin solution In one embodiment, the polymer matrix of the present disclosure obtained by polymerizing a monomer is dissolved in a solvent to produce a resin solution. Examples of preferred solvents include heptane, octane, and limonene.

(3-4) Method for preparing conductive material In one embodiment, the conductive material is obtained by mixing the resin solution obtained in (3-3) with a conductive component and, if necessary, a dispersant, and heating the resulting mixture. Those skilled in the art can also prepare the conductive material by using any method other than this method, using the description herein and any method known in the art.

(Explanation of conductive components)
Examples of conductive components that can be used by the conductive material of the present disclosure include natural graphite such as flake graphite, graphite such as artificial graphite, carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black, carbon-based materials such as graphene, carbon nanotubes, and fullerene; conductive fibers such as carbon fibers and metal fibers; carbon fluoride; powders of metal particles such as copper, gold, nickel, tin, aluminum, zinc, iron, and silver; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; and organic conductive materials such as polyphenylene derivatives, but the present disclosure is not limited to only these examples. These conductive components may be used alone or in combination of two or more types. Among these conductive components, from the viewpoint of obtaining a conductive film that is excellent in workability and moldability as well as flexibility and elongation, carbon nanotubes, carbon black, graphene, and metal particles are preferred, and carbon nanotubes, carbon black, graphene, and silver particles are more preferred.

The solid content of the conductive component in the total solid content of the polymer matrix and the conductive component cannot be determined in general because it varies depending on the type of the conductive component, but from the viewpoint of obtaining a conductive film that is excellent in workability and formability as well as flexibility and extensibility, it is preferably 1 mass % or more, and from the viewpoint of obtaining a conductive film that is excellent in workability and formability as well as flexibility and extensibility, it is preferably 100 mass % or less.

The content of the solid content of the conductive component in the total solid content of the polymer matrix and the conductive component is preferably 1% by mass or more, more preferably 1.5% by mass or more, and even more preferably 2% by mass or more, in the case of a conductive carbon-based component, from the viewpoint of obtaining a conductive film having excellent workability and formability as well as excellent flexibility and elongation, and is preferably 25% by mass or less, more preferably 20% by mass or less, even more preferably 15% by mass or less, and even more preferably 3.5 to 10% by mass, in the case of a conductive carbon-based component, from the viewpoint of obtaining a conductive film having excellent workability and formability as well as excellent flexibility and elongation. On the other hand, in the case of a conductive component of a metal-based component, from the viewpoint of imparting good conductivity, it is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more, and from the viewpoint of obtaining a conductive film having excellent workability and formability, it is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less.

(Applications of conductive materials)
The conductive material of the present disclosure can be suitably used as a conductive film that can be suitably used in, for example, sensors, wiring, electrodes, substrates, power generating elements, speakers, microphones, noise cancellers, transducers, artificial muscles, small pumps, medical instruments, and the like used in actuators and industrial robots, and can also be suitably used as a raw material for the conductive films.

Preferred Embodiments
The preferred embodiments of the present disclosure are described below. The embodiments provided below are provided for a better understanding of the present disclosure, and it is understood that the scope of the present disclosure should not be limited to the following description. Therefore, it is clear that a person skilled in the art can make appropriate modifications within the scope of the present disclosure in light of the description in this specification. It is also understood that the following embodiments of the present disclosure can be used alone or in combination.

(For improving electrical conductivity)
In one aspect, the present disclosure relates to electrical conductivity enhancement applications.

More specifically, in a specific aspect, the present disclosure provides a composition (conductivity enhancer) or combination for improving the electrical conductivity of a conductor, comprising at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, at least one compound from a group of halogen-containing (meth)acrylic monomer components, and at least one compound from a group of hydroxy-containing (meth)acrylic monomer components.

In the past, in systems where a large amount of silver filler is present, as in the present disclosure, it was thought that the polymer composition would not affect conductivity, and so sufficient consideration had not been given to this. However, as a result of polymer consideration, it was confirmed that in a system in which a fluorinated alkyl acrylate, an ether moiety-containing acrylate, and a hydroxyl-containing acrylate were copolymerized, the resistivity was lower than that of conventional products. Further investigation confirmed that the resistivity decreased as the fluorine atom content in the fluorinated alkyl acrylate increased. From the viewpoint of resin solubility, it was decided to use 2,2,2-trifluoroethyl acrylate (V#3F) in this system.

In one specific embodiment, the conductive material of the present disclosure includes a copolymer of an alkoxy-substituted alkyl acrylate, which is an embodiment of an ether moiety-containing (meth)acrylic monomer, a fluorinated alkyl (meth)acrylate, which is an embodiment of a halogen-containing (meth)acrylic monomer, and a hydroxy-containing acrylate, which is an embodiment of a hydroxy-containing (meth)acrylic monomer, and a conductive component. In this way, the copolymer can improve the conductivity of the conductive component.

By providing this technology of the present disclosure, the conductivity of any conductive component can be improved.

In one preferred embodiment, the copolymer used in the present disclosure is advantageously a copolymer of an alkoxy-substituted alkyl acrylate, a fluorinated alkyl (meth)acrylate, and a hydroxy-containing acrylate. The reason for this, without wishing to be bound by theory, is the effect of repelling compounds (surface activity effect). Fluorine-based resins are used as antifouling coating agents and release agents, and have the effect of repelling compounds (surface activity effect). As for the reason for the decrease in resistivity in the present disclosure, it is believed that the fluorine compound's surface activity effect caused the fluorinated alkyl (meth)acrylate to repel the silver particles, resulting in the silver particles becoming more densely packed together. In addition, it is believed that the polarity of the copolymer also affects the decrease in resistivity, and it is believed that these factors have a combined effect, causing the resistivity to decrease. Furthermore, it is an unexpected result that the effect is believed to be manifested with a small amount of addition such as in the examples.

In one embodiment, the conductive component is similar to the conductivity enhancer described above.

によって表される第一の（メタ）アクリレートであり、式中、Ｒ^１は、水素原子またはメチル基であり、
Ｒ^２は、アルキルオキシ基、シクロアルキルオキシ基もしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールである。 In one embodiment, the ether moiety-containing (meth)acrylic monomer component compound has the formula (1):

wherein R ¹ is a hydrogen atom or a methyl group;
^R2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group.

In one embodiment, ^R2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with an alkyloxy group. In one embodiment, ^R2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a cycloalkyloxy group. In one embodiment, ^R2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with an aryloxy group.

In one embodiment, the compound represented by formula (1) is an alkyl(meth)acrylate substituted with an alkyloxy group, a cycloalkyloxy group, or an aryloxy group. In one embodiment, the compound represented by formula (1) is an alkyl(meth)acrylate substituted with an alkyloxy group or a cycloalkyloxy group. In one embodiment, the compound represented by formula (1) is an alkyloxy-substituted alkyl(meth)acrylate.

によって表される第二の（メタ）アクリレートであり、式中、Ｒ^３およびＲ^４は、本明細書中で定義されるとおりである。 In one embodiment, the halogen-containing (meth)acrylic monomer component group compound is represented by the formula (2):

where R ³ and R ⁴ are as defined herein.

In one embodiment, R ⁴ is an alkyl group, a cycloalkyl group, or an aryl group substituted with a halogen group. In one embodiment, R ⁴ is an alkyl group, a cycloalkyl group, or an aryl group substituted with a fluorine atom. In one embodiment, R ⁴ is an alkyl group, a cycloalkyl group, or an aryl group substituted with a chlorine atom. In one embodiment, R ⁴ is an alkyl group, a cycloalkyl group, or an aryl group substituted with a bromine atom.

In one embodiment, the compound represented by formula (2) is a haloalkyl(meth)acrylate.

によって表される第三の（メタ）アクリレートであり、式中、Ｒ^５およびＲ^６は、本明細書中で定義されるとおりである。 In one embodiment, the hydroxy-containing (meth)acrylic monomer component group compound has the formula (3):

wherein R ⁵ and R ⁶ are as defined herein.

In one embodiment, ^R6 is an alkyl group substituted with a hydroxy group. In one embodiment, ^R6 is a cycloalkyl group substituted with a hydroxy group. In one embodiment, ^R6 is an aryl group substituted with a hydroxy group.

In one embodiment, the compound represented by formula (3) is a hydroxy-substituted alkyl (meth)acrylate. In a preferred embodiment, the compound represented by formula (3) is 4-hydroxybutyl acrylate.

The hydroxy-containing (meth)acrylate may be used with a corresponding suitable crosslinking agent, examples of which include, but are not limited to, isocyanate, hexamethylene diisocyanate, polyisocyanate, Duranate ^™ (manufactured by Asahi Kasei Corporation), and the like.

In one embodiment, the alkyl (meth)acrylate substituted with a hydroxy group is used together with a corresponding suitable crosslinking agent as necessary. In one embodiment, the alkyl (meth)acrylate substituted with a hydroxy group may be used together with a crosslinking agent as necessary to crosslink. Examples of crosslinking agents include, but are not limited to, formaldehyde and isocyanate. By using the crosslinking agent together, the durability of the binder resin can be improved, and the flexibility and/or durability of the conductive material can be improved.

により表される第四の（メタ）アクリレートであり、式中、Ｒ^７は、水素原子またはメチル基であり、Ｒ^８は、非置換のアルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^８はエーテル、ハロゲンおよび水酸基で置換されたアルキル、シクロアルキル、またはアリールではない。 In one embodiment, the unsubstituted alkyl (meth)acrylic monomer component group compound has the formula (4):

wherein ^R7 is a hydrogen atom or a methyl group, and ^R8 is an unsubstituted alkyl, cycloalkyl, or aryl, with the proviso that ^R8 is not an alkyl, cycloalkyl, or aryl substituted with an ether, a halogen, or a hydroxyl group.

In one embodiment, ^R8 is an unsubstituted alkyl group. In one embodiment, ^R8 is an unsubstituted cycloalkyl group. In one embodiment, ^R8 is an unsubstituted aryl group.

In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 to 24 carbon atoms.

In another embodiment, R ⁸ is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13 to 24 carbon atoms.

In yet another embodiment, R ⁸ is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18 to 24 carbon atoms.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, (3-ethyloxetan-3-yl)methyl acrylate, or 2,3-epoxypropyl methacrylate.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate.

In one embodiment, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate.

In one embodiment, the compound represented by formula (3) is 4-hydroxybutyl acrylate.

In one embodiment, an isocyanate is used as a crosslinking agent to crosslink the compound represented by formula (3).

In one embodiment, the compound represented by formula (4) is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.

In yet another embodiment, the ether moiety-containing (meth)acrylic monomer is (2-methoxyethyl acrylate, (3-ethyloxetan-3-yl)methyl acrylate, or 2,3-epoxypropyl methacrylate.

In yet another embodiment, the halogen-containing (meth)acrylate is 2,2,2-trifluoroethyl acrylate.

In yet another embodiment, the hydroxy-containing (meth)acrylate is 4-hydroxybutyl acrylate.

In another embodiment, the unsubstituted alkyl (meth)acrylate is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.

In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, and the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate.

In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, and the compound represented by formula (3) is 4-hydroxybutyl acrylate.

In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, and the compound represented by formula (3) is 4-hydroxybutyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is isostearyl acrylate.

In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is isostearyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is ethyl acrylate.

In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is ethyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.

In one embodiment, the mass ratio of A) at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, B) at least one compound of the group of halogen-containing (meth)acrylic monomer components, and C) at least one compound of the group of hydroxyl-containing (meth)acrylic monomer components is A:B:C=20-80:80-20:0.2-2.0, and can be A:B:C=25-70:70-25:0.3-1.5, and can further be A:B:C=29-65:70-35:0.5-1.5. When a crosslinking agent is further contained, the ratio of A:B:C:crosslinking agent=20-80:80-20:0.2-2.0:0.2-2.0 can be A:B:C:crosslinking agent=25-70:70-25:0.3-1.5:0.3-1.5, and further, the ratio of A:B:C:crosslinking agent=29-65:70-35:0.5-1.5:0.5-1.5 can be A:B:C:crosslinking agent=29-65:70-35:0.5-1.5:0.5-1.5. When the composition further contains at least one compound selected from D) a group of unsubstituted alkyl (meth)acrylic monomer components, the ratio A:B:C:D is 20-80:80-20:0.2-2.0:10-70, A:B:C:D can be 25-70:70-25:0.3-1.5:20-60, and further A:B:C:D can be 29-65:70-35:0.5-1.5:30-50. If a crosslinking agent is further included, the ratio of A:B:C:D:crosslinking agent is 20-80:80-20:0.2-2.0:10-700.2-2.0, A:B:C::D crosslinking agent is 25-70:70-25:0.3-1.5:20-60:0.3-1.5, and A:B:C:D:crosslinking agent is 29-65:70-35:0.5-1.5:30-50:0.5-1.5. The same applies to the ratio of each monomer component group in the copolymer described below.

(Conductive material)
In another aspect, the present disclosure provides a conductive material having improved electrical conductivity.

In one specific aspect, the present disclosure provides a conductive material comprising a copolymer of a compound including an ether moiety-containing (meth)acrylic monomer component group, a halogen-containing (meth)acrylic monomer component group, and a hydroxyl-containing (meth)acrylic monomer component group, and optionally including a crosslinker, and a conductive component. Preferred embodiments of the conductive material may utilize any of the embodiments described herein or a combination thereof, and may be applied in combination with one or more of the embodiments described in the section (Applications for Improving Electrical Conductivity) of this specification.

(Production method)
In one aspect, the present disclosure provides a method for producing the conductive materials and conductivity enhancers of the present disclosure.

In a specific aspect, the present disclosure provides a method for producing a conductive material comprising a homopolymer or copolymer of a compound containing at least one of an ether moiety-containing (meth)acrylic monomer component group, a halogen-containing (meth)acrylic monomer component group, a hydroxyl-containing (meth)acrylic monomer component group, and an unsubstituted alkyl (meth)acrylic monomer component group, and optionally a crosslinker, and a conductive component. The method includes a step of obtaining a copolymer by polymerizing the monomer and a polymerizable monomer, a step of mixing the copolymer and the conductive component to obtain a mixture, and a step of heating the mixture to produce a conductive material. A preferred embodiment of the production method can utilize any embodiment or combination thereof described herein, and can be applied in combination with one or more of any embodiments described in the section (Conductivity Improvement Application) of this specification.

In the process of obtaining a copolymer by photopolymerizing the monomer and the polymerizable monomer in the manufacturing method disclosed herein, the following conditions are typically preferred: atmospheric pressure, 5°C to 100°C.

In the process of mixing the copolymer and the conductive component to obtain a mixture in the manufacturing method of the present disclosure, the following conditions are typically preferred: stirring with a planetary mixer at room temperature under atmospheric pressure.

In the manufacturing method of the present disclosure, the process of heating the mixture to produce the conductive material typically uses the following conditions: atmospheric pressure, 120°C to 150°C.

(Copolymer)
The present disclosure provides copolymers using the techniques of the present disclosure.

In a specific aspect, the present disclosure is a copolymer of an ether moiety-containing (meth)acrylate, a halogen-containing (meth)acrylate, and a hydroxy-containing (meth)acrylate.

によって表されるモノマーであり、
前記ハロゲン含有（メタ）アクリレートは、式（２）

によって表されるモノマーであり、
前記ヒドロキシ含有（メタ）アクリレートは、式（３）

によって表されるモノマーであり、
式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、およびＲ^８は、本明細書中で定義されるとおりである。 In an exemplary embodiment, the ether moiety-containing (meth)acrylate has the formula (1):

is a monomer represented by
The halogen-containing (meth)acrylate is represented by the formula (2):

is a monomer represented by
The hydroxy-containing (meth)acrylate is represented by the formula (3):

is a monomer represented by
wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R ⁸ are as defined herein.

In one embodiment, ^R6 is an alkyl group substituted with one or more hydroxy groups.

In one embodiment, the copolymer is a copolymer including an alkoxy-substituted alkyl (meth)acrylate and a haloalkyl (meth)acrylate.

The hydroxy-containing (meth)acrylate may be used with a crosslinking agent during copolymerization.

The copolymer is used, for example, as a matrix for a conductive material.

In one embodiment, the copolymer is a copolymer of the ether moiety-containing (meth)acrylate represented by formula (1), the halogen-containing (meth)acrylate represented by formula (2), and the hydroxyl-containing (meth)acrylate represented by formula (3).

In one embodiment, the copolymer is a copolymer of an alkoxy-substituted alkyl (meth)acrylate, a haloalkyl (meth)acrylate, and a hydroxy-substituted alkyl (meth)acrylate.

によって表され、
式中、Ｒ^１は、水素原子またはメチル基であり、Ｒ^２は、アルキルオキシ基、シクロアルキルオキシ基もしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールであり、
該ハロゲン含有基で置換されたアルキル（メタ）アクリレートは、式（２）

によって表され、
式中、Ｒ^３は、水素原子またはメチル基であり、
Ｒ^４は、１個から置換可能な数までの同一又は異なるハロゲン原子で置換されたアルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^４は、エーテル基を含むアルキル、シクロアルキル、またはアリールではなく、
該ヒドロキシ含有（メタ）アクリルモノマーは、式（３）、

によって表され、
式中、Ｒ^５は、水素原子またはメチル基であり、Ｒ^６は、ヒドロキシ基で置換されている、アルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^６はエーテルおよびハロゲンで置換されたアルキル、シクロアルキル、またはアリールではなく、該ヒドロキシ含有（メタ）アクリルモノマーは、必要に応じて架橋剤を用いて架橋されてもよい。このコポリマーは、例えば、導電材のマトリクスとして使用される。 The present disclosure also relates to a method for preparing a copolymer of an ether moiety-containing (meth)acrylic monomer, an alkyl (meth)acrylate substituted with a halogen-containing group, and a hydroxy-containing (meth)acrylic monomer,
The ether moiety-containing (meth)acrylic monomer has the formula (1):

is represented by
In the formula, R ¹ is a hydrogen atom or a methyl group, R ² is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group,
The halogen-containing group-substituted alkyl(meth)acrylate is represented by the formula (2):

is represented by
In the formula, ^R3 is a hydrogen atom or a methyl group;
^R4 is an alkyl, cycloalkyl, or aryl substituted with 1 to a substitutable number of the same or different halogen atoms, provided that ^R4 is not an alkyl, cycloalkyl, or aryl containing an ether group;
The hydroxy-containing (meth)acrylic monomer has the formula (3):

is represented by
wherein ^R5 is a hydrogen atom or a methyl group, ^R6 is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group, with the proviso that ^R6 is not an alkyl, cycloalkyl, or aryl substituted with an ether or halogen, and the hydroxy-containing (meth)acrylic monomer may be crosslinked with a crosslinking agent as necessary. The copolymer is used, for example, as a matrix for a conductive material.

により表される（メタ）アクリレートであり、式中、Ｒ^７およびＲ^８は、本明細書中で定義されるとおりである。 In one embodiment, the present disclosure relates to a method of making a copolymer, wherein the copolymer comprises an unsubstituted alkyl (meth)acrylate,
The unsubstituted alkyl (meth)acrylate is represented by the formula (4):

where R ⁷ and R ⁸ are as defined herein.

In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11 to 24 carbon atoms.

In one embodiment, R ⁸ is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13 to 24 carbon atoms.

In one embodiment, R ⁸ is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18 to 24 carbon atoms.

The present disclosure provides matrix applications.
In one aspect, the present disclosure includes copolymers of compounds comprising at least one of ether moiety-containing (meth)acrylic monomer components of formula (1), halogen-containing (meth)acrylic monomer components of formula (2), hydroxy-containing (meth)acrylic monomer components of formula (3), and unsubstituted alkyl (meth)acrylic monomer components of formula (4), and optionally including a crosslinker:
A composition for use as a matrix in a conductive material is provided that includes a conductive component.

(Mixture)
The present disclosure also provides mixtures.

In one aspect, the present disclosure provides a mixture of matter (i.e., a composition including a copolymer and a metal-based component). Specifically, the present disclosure provides a mixture of the copolymer and a metal.

In a representative embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1) and at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), and a mixture of a metal.

In one embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1), at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), at least one compound of the hydroxyl-containing (meth)acrylic monomer component group of formula (3), and a mixture of a metal.

In one embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1), at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), at least one compound of the hydroxy-containing (meth)acrylic monomer component group of formula (3), at least one compound of the unsubstituted alkyl (meth)acrylic monomer component group of formula (4), and a mixture of a metal.

In one embodiment, the metal includes silver, copper, gold, aluminum, zinc, tin, nickel, and/or iron. In a preferred embodiment, the metal is silver. Without wishing to be bound by theory, silver is both a good conductor of electricity and is durable.

(Note)
In this specification, "or" is used when "at least one or more" of the items listed in the sentence can be employed. The same applies to "alternative." In this specification, when it is specified that "within a range of two values," the range includes the two values themselves.

All references cited herein, including scientific literature, patents, patent applications, and the like, are hereby incorporated by reference in their entirety to the same extent as if each was specifically set forth herein.

The present disclosure has been described above by showing preferred embodiments for ease of understanding. Below, the present disclosure will be described based on examples, but the above description and the following examples are provided for illustrative purposes only and are not provided for the purpose of limiting the present disclosure. Therefore, the scope of the present disclosure is not limited to the embodiments or examples specifically described in this specification, but is limited only by the scope of the claims.

The following examples are provided. When necessary, the handling of organisms used in the following examples complied with standards set by regulatory authorities. Specific reagents used were those listed in the examples, but equivalent products from other manufacturers (such as Sigma-Aldrich) can also be used.

Example A: Preparation of polymer matrix
In this example, a polymer matrix was prepared.

Example 1
A monomer component containing a polymerization initiator was obtained by mixing 2-methoxyethyl acrylate (62 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name 2-MTA) as monomer A, 2,2,2-trifluoroethyl acrylate (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat V#3F) as monomer B, 4-hydroxybutyl acrylate (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat 4-HBA) as monomer C, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g, manufactured by BASF Corporation, trade name Irgacure (registered trademark) TPO) as a polymerization initiator, and α-methylstyrene dimer (1 g, manufactured by NOF Corporation, trade name Nofmer MSD) as a chain transfer agent. The obtained monomer component was poured into a transparent glass mold (length: 100 mm, width: 100 mm, depth: 2 mm), and then the monomer component was irradiated with ultraviolet light so that the exposure dose was 0.36 mW/ ^cm2 . The monomer component was bulk polymerized for 2 hours to obtain a polymer.

Preparation of Conductive Material Precursor The obtained polymer (2.50 g) was dissolved in 3-methoxy-3-methyl-1-butanol (7.50 g) to obtain a resin solution.
The above resin solution (4.00 g) was mixed with silver filler (4.00 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., product name AgC-A), a crosslinking agent (0.010 g, manufactured by Asahi Kasei Corporation, product name MF-K60B), 2-(2-butoxyethoxy)ethanol (0.10 g) as a dispersant, and a rheology adjuster (0.010 g, manufactured by BYK-Chemie Japan, product name RHEOBYK-410) using a Mazerustar manufactured by Kurabo Industries, to obtain a conductive material precursor.

(Film formation)
The obtained conductive material precursor was applied to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tohcello Inc., product name Separator SP-PET PET-01-Bu) as a release film to form a coating film.

(Conductive film)
The resulting coating was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.

(Examples 2 to 4)
An acrylic resin solution was obtained in the same manner as in Example 1, except that the ratios of monomer A, monomer B, monomer C and the crosslinking agent were changed as shown in the table below.

Example 5
An acrylic resin solution was obtained in the same manner as in Example 1, except that ethyl acrylate (EA, 31 g) was newly added as monomer D, and 2-methoxyethyl acrylate (31 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name 2-MTA) as monomer A, 2,2,2-trifluoroethyl acrylate (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat V#3F) as monomer B, 4-hydroxybutyl acrylate (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat 4-HBA) as monomer C, isocyanate (1 g) as a crosslinking agent, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g, manufactured by BASF, trade name Irgacure (registered trademark) TPO) as a polymerization initiator were mixed in the above amounts.

(Comparative Examples 1 and 2)
The corresponding polymer was obtained by using only 2-MTA (monomer A) and V#3F (monomer B) as monomers. The weight parts of the monomers A and B used are shown in Table 1.

(Comparative Example 3)
Similarly, the corresponding polymer was obtained using V#3F (monomer B), 4-HBA (monomer C) and isocyanate (crosslinking agent). The weight parts of the monomer B, monomer C and crosslinking agent used are as shown in Table 1.

(Comparative Example 4)
Similarly, the corresponding polymer was obtained using V#3F (monomer B), 4-HBA (monomer C), isocyanate (crosslinking agent) and EA (monomer D). The weight parts of the monomer B, monomer C and crosslinking agent used are as shown in Table 1.

Example B: Preparation of Conductive Film
In this example, a conductive film was prepared.

(Conductive material precursor)
Each acrylic resin solution (6.00 g) obtained in Example A was mixed with silver filler (7.20 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., product name AgC-A) and 2-(2-butoxyethoxy)ethanol (0.10 g) as a dispersant using a Mazerustar manufactured by Kurabo Industries Co., Ltd. to obtain a conductive material precursor.

(Film formation)
The obtained conductive material precursor was applied to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tocello Inc., product name Separator SP-PET PET-01-Bu) as a release film to form a coating film.

(Conductive film)
The resulting coating was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.

(result)
Conductive films were prepared according to the procedures described in Examples A and B. The results are shown in Table 1.

Example C: Measurement of Volume Resistivity
The conductive film obtained in Example B was cut into a piece having a length of 0.5 cm and a width of 2.00 cm, and was measured by a four-terminal method using Loresta GP (manufactured by Mitsubishi Chemical Analytech Co., Ltd.).

(result)
The results are shown in Table 1.

(Example D: Confirmation of change in resistance value)
In this embodiment, the change in resistance value was confirmed.

(Resistance measurement)
The conductive film obtained above was cut into a piece having a length of 0.5 cm and a width of 2.00 cm, and the resistance value (ΩA) before stretching was measured using a digital multimeter (manufactured by Sanwa Denki Keiki Co., Ltd., product name PC773) with the interelectrode distance fixed at 1.00 cm.

(Resistance change)
Next, while the conductive film was fixed on the multimeter electrodes, the distance between the electrodes was set to 2.00 cm, and the resistance value (ΩB) in this state was measured. The change in resistance value was calculated as follows.
Resistance change = ΩB/ΩA

(result)
The results are shown in Table 1. The smaller the change in resistance value (closer to 1), the smaller the effect of the shape change, which means higher durability. Therefore, the change in resistance value can also be evaluated as durability.

Example E: Measurement of Flexibility
The conductive film obtained in the above example was cut into a test piece (dumbbell-shaped No. 7). The flexibility of this test piece was measured at a tension speed of 50 mm/min using a tensile tester (manufactured by A&D Co., Ltd.: product name TENSILON RTG-1310). Young's modulus was calculated from the obtained value.

(result)
The results are shown in Table 1.

(Note)
Although the present disclosure has been illustrated using the preferred embodiments thereof, it is understood that the present disclosure should be interpreted in scope only by the claims. It is understood that the patents, patent applications, and other documents cited in this specification are incorporated by reference into this specification in the same manner as if the contents themselves were specifically set forth herein.

The conductive material enhancer disclosed herein can be used to provide an efficient conductive material, which can be used in industries that require conductive materials.

Claims (14)

A) at least one compound from the group of ether moiety-containing (meth)acrylic monomer components;
B) at least one compound from a group of halogen-containing (meth)acrylic monomer components;
C) at least one compound from the group consisting of hydroxy-containing (meth)acrylic monomer components;
A conductivity enhancer for improving the conductivity of a conductor, comprising:
The compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1)

is a first (meth)acrylate represented by
R ¹ is a hydrogen atom or a methyl group;
R2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group ^;
The compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2)

is a second (meth)acrylate represented by
R3 is a hydrogen atom or a methyl group ^;
R4 is an alkyl, cycloalkyl, or aryl substituted with 1 to a substitutable number of the same or different halogen atoms ^;
At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3)

and a third (meth)acrylate represented by
R5 is a hydrogen atom or a methyl group ^;
The conductivity enhancer, ^wherein R6 is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group . The conductivity enhancer of claim 1 , further comprising a cross-linking agent. The electrical conductivity improver according to claim 2 , wherein the crosslinking agent has a functional group that crosslinks the compounds of the component group C. The electrical conductivity improver according to any one of claims 1 to 3, further comprising at least one compound selected from the group consisting of D) unsubstituted alkyl (meth)acrylic monomer components. At least one compound of the unsubstituted alkyl (meth)acrylic monomer component group is represented by the formula (4)

and a fourth (meth)acrylate represented by
^R7 is a hydrogen atom or a methyl group;
R ⁸ is unsubstituted alkyl, cycloalkyl, or aryl;
The electrical conductivity enhancer according to claim 4 . The conductivity improver according to any one of claims 1 to 4, wherein the first (meth)acrylate includes at least one selected from the group consisting of tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, and (5-ethyl- 1,3 -dioxane-5-yl) methyl (meth)acrylate . The electrical conductivity improver according to any one of claims 1 to 6, wherein the second (meth)acrylate includes at least one selected from the group consisting of 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, and 1H ,1H,2H,2H- tridecafluorooctyl (meth)acrylate . The electrical conductivity improver according to any one of claims 1 to 7, wherein the third (meth)acrylate includes at least one selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4 -hydroxybutyl (meth) acrylate . The electrical conductivity enhancer according to claim 5 , wherein the fourth (meth)acrylate comprises at least one selected from the group consisting of ethyl acrylate, isostearyl acrylate, stearyl acrylate, and lauryl acrylate. A conductive material comprising a polymer matrix obtained by polymerizing the conductivity enhancer according to any one of claims 1 to 9 , a conductive component, and a substrate. 11. The conductive material of claim 10 , wherein the conductive component comprises a metal component, a metal oxide, a metal-based component of a metal carbide , a conductive carbon-based component, a conductive organic compound, a conductive polymer, or a combination thereof. The electrical conductivity improver according to any one of claims 1 to 9 , which improves the flexibility of an electrically conductive component or an electrically conductive material . The electrical conductivity improver according to any one of claims 1 to 9 , which improves durability of an electrically conductive component or an electrically conductive material . A) at least one compound from the group of ether moiety-containing (meth)acrylic monomer components;
B) at least one compound from a group of halogen-containing (meth)acrylic monomer components;
C) at least one compound from the hydroxy-containing (meth)acrylic monomer component group;
a polymer matrix obtained by polymerizing
A solvent;
A mixture of a conductive component,
The compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1)

is a first (meth)acrylate represented by
R ¹ is a hydrogen atom or a methyl group,
R ² is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group;
The compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2)

is a second (meth)acrylate represented by
R ³ is a hydrogen atom or a methyl group,
R ⁴ is an alkyl, cycloalkyl, or aryl substituted with one or more of the same or different halogen atoms, up to the maximum number of which can be substituted;
At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3)

and a third (meth)acrylate represented by
R ⁵ is a hydrogen atom or a methyl group,
R ⁶ is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group;