Conductive polymer composition and use thereof

Abstract

The problem with conventionally known conductive materials has been low dispersibility in an adhesive, a resin, a mold release agent, or the like. In order to solve the above problem, the present invention uses a conductive polymer composition characterized by comprising: (A) a polythiophene containing two or more structural units which are at least one kind selected from the group consisting of structural units represented by general formula (1) and structural units represented by general formula (2); and (B) a polyether-based compound represented by general formula (16).

Description

Conductive polymer composition and its uses

[0001] The present invention relates to a conductive polymer composition and its uses.

[0002] Generally, static electricity refers to the phenomenon in which an object accumulates an electric charge, or the electric charge itself. Static electricity can be generated by the accumulation of electric charges caused by friction between two types of dielectrics, or by contact with a charged object, and can accumulate on the surface of an object.

[0003] The static electricity can cause foreign matter such as dust to be sucked in, electrostatic damage to devices, malfunction of measuring instruments, fires, etc., and therefore advanced anti-static measures are required, particularly in the electronics industry.

[0004] An example of an electronics product is a liquid crystal panel element. Liquid crystal panel elements are manufactured by bonding a polarizing plate to glass substrates sandwiching a liquid crystal layer. The bonded polarizing plate is supplied as a three-layer structure consisting of a polarizing plate, an adhesive layer for adhesion, and a protective film protecting the adhesive layer. The protective film is peeled off when the polarizing plate is bonded to the glass substrate. If the adhesive layer and the protective film are both highly insulating, static electricity is generated upon peeling, and the adhesive layer is easily charged. If the polarizing plate is bonded to the glass substrate in a charged state, dust attraction and liquid crystal molecular alignment disorder occur, increasing the risk of reduced yield and quality of the liquid crystal panel element. For this reason, there is a demand for imparting antistatic properties to the adhesive layer. As a means to achieve this, for example, blending a conductive material (e.g., an ionic compound or a conductive complex containing a π-conjugated conductive polymer and a polyanion) into the adhesive composition used to form the adhesive layer has been proposed (Patent Documents 1 to 3).

[0005] Japanese Patent Application Publication No. 2014-058679 Japanese Patent Application Publication No. 2022-092880 Japanese Patent Application Publication No. 2020-529511

[0006] However, conventionally known conductive materials have a problem in that they have low dispersibility in adhesives, resins, release agents, and the like.

[0007] A conductive polymer composition according to one aspect of the present invention is characterized by comprising a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and a polyether-based compound (B) represented by the following general formula (16):

[0008] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0009] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0010] The conductive adhesive film according to one embodiment of the present invention is characterized by comprising a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), a polyether compound (B) represented by the following general formula (16), and an adhesive (D):

[0011] [In the general formula (1), M ＋represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0012] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0013] The conductive hard coat according to one embodiment of the present invention is characterized by comprising a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and a polyether compound (B) represented by the following general formula (16):

[0014] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0015] [In the general formula (16), R ５Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0016] The conductive release layer according to one embodiment of the present invention is characterized by comprising a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and a polyether compound (B) represented by the following general formula (16):

[0017] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0018] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0019] According to one aspect of the present invention, it is possible to provide a conductive polymer composition that has high dispersibility in adhesives, resins, release agents, and the like.

[0020] An embodiment of the present invention will be described in detail below. In this specification, unless otherwise specified, the numerical range "A to B" means "A or more and B or less."

[0021] Currently, commonly used adhesives are manufactured using acetate ester-based solvents. When adding additives to an adhesive to impart functionality, the additives must be uniformly mixed into the adhesive, and therefore the additives must have excellent compatibility with acetate ester-based solvents. Among conventionally known conductive materials, none have been found to have excellent compatibility with acetate ester-based solvents. However, the conductive polymer composition according to one embodiment of the present invention has been found to have excellent compatibility with acetate ester-based solvents, allowing it to be uniformly dispersed in commercially available adhesives, thereby imparting excellent antistatic properties to the adhesives.

[0022] According to one embodiment of the present invention, a new pressure-sensitive adhesive composition having antistatic properties based on a conductive polymer composition that has not been reported before can be provided.

[0023] Furthermore, according to one embodiment of the present invention, it is possible to provide a conductive adhesive that is less susceptible to deterioration in quality due to aggregation of the conductive material, etc., compared to previously reported adhesives.

[0024] Furthermore, with the above-described configuration, for example, by applying the conductive adhesive according to one embodiment of the present invention to a liquid crystal panel, etc., it is possible to reduce the rate of product defects caused by static electricity. Such an effect also contributes to the achievement of, for example, Goal 12 of the Sustainable Development Goals (SDGs) advocated by the United Nations, "Ensure sustainable consumption and production patterns."

[0025] A conductive polymer composition according to one embodiment of the present invention comprises a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and a polyether-based compound (B) represented by the following general formula (16):

[0026] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0027] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, with the proviso that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0028] M in the above general formula (1) ＋ This will be discussed later.

[0029] In the above general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group. The organic group having a total of 1 to 18 carbon atoms in a state in which it does not have at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a hexyl group, an isohexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, an isobutoxymethyl group, a tert-butoxymethyl group, a hexyloxymethyl group, an isohexyloxymethyl group, a heptyloxymethyl group, and an octyloxymethyl group.

[0030] In the above general formulas (1) and (2), the organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group is not particularly limited, and examples thereof include a methyl sulfonate group, a methyl phosphonate group, a 2-ethyl sulfonate group, a 2-ethyl phosphonate group, a 3-propyl sulfonate group, a 3-propyl phosphonate group, a 2-propyl sulfonate group, a 2-propyl phosphonate group, a 4-butyl sulfonate group, a 4-butyl phosphonate group, a 3-butyl sulfonate group, a 3-butyl phosphonate group, a 6-hexyl sulfonate group, a 6-hexyl phosphonate group, a 5-hexyl sulfonate group, a 5-hexyl phosphonate group, a 5-butyl phosphonate group, a 6-hexyl hexyl phosphonate group, a 5-hexyl hexyl sulfonate group, a 5-butyl phosphonate ... Examples of the alkyl group include a hexyl phosphate group, a methoxymethyl sulfonate group, a methoxymethyl phosphonate group, a 2-ethoxymethyl sulfonate group, a 2-ethoxymethyl phosphonate group, a 3-propoxymethyl sulfonate group, a 3-propoxymethyl phosphonate group, a 2-propoxymethyl sulfonate group, a 2-propoxymethyl phosphonate group, a 4-butoxymethyl sulfonate group, a 4-butoxymethyl phosphonate group, a 3-butoxymethyl sulfonate group, a 3-butoxymethyl phosphonate group, a hexyloxymethyl 6-sulfonate group, a hexyloxymethyl 6-phosphonate group, a hexyloxymethyl 5-sulfonate group, and a hexyloxymethyl 5-phosphonate group.

[0031] The structural unit represented by the general formula (2) represents the doped state of the structural unit represented by the general formula (1), and the doped state is realized by the sulfonic acid group or phosphonic acid group in the structural unit represented by the general formula (1) acting as a p-type dopant.

[0032] The polythiophene (A) is more preferably a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (3) and a structural unit represented by the following general formula (4), in terms of excellent film-forming properties:

[0033] [In the general formula (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium ion.２ represents a hydrogen atom, a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 6 carbon atoms, or a fluorine atom; m represents an integer of 1 to 10; and n represents 0 or 1.

[0034] The structural unit represented by the general formula (4) represents the doped state of the structural unit represented by the general formula (3), and the doped state is realized by the sulfo group or sulfonate group in the structural unit represented by the general formula (3) acting as a p-type dopant.

[0035] R in the above general formulas (3) and (4) ２ The linear or branched alkyl group having 3 to 6 carbon atoms, represented by the formula (I), is not particularly limited, and examples thereof include an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a cyclopentyl group, an n-hexyl group, a 2-ethylbutyl group, and a cyclohexyl group.

[0036] R ２ In terms of excellent film-forming properties, is preferably a hydrogen atom, a methyl group, an ethyl group, or a fluorine atom, more preferably a hydrogen atom, a methyl group, or a fluorine atom, and even more preferably a methyl group.

[0037] In the above general formulas (1) and (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium ion.

[0038] The alkali metal ions are not particularly limited, but examples thereof include lithium ions, sodium ions, potassium ions, rubidium ions, and cesium ions.

[0039] The conjugate acid of the amine compound is a cationic compound in which a proton is added to an amine compound. The amine compound is not particularly limited, but examples thereof include ammonia, a compound represented by the general formula NH ２ (R ６ ), NH(R ７ ) (R ８ ), and N(R６ ) (R ７ ) (R ８ ) as an amine compound, a pyridine compound, or an imidazole compound.

[0040] The above R ６ ~R ８ each independently represent an alkyl group having a total of 1 to 40 carbon atoms which may have a substituent (among these, alkyl groups having 3 to 40 carbon atoms may be linear, branched, or cyclic), but in terms of excellent dispersibility in adhesives, resins, release agents, etc., it is more preferable that each independently represent an alkyl group having a total of 1 to 20 carbon atoms which may have a substituent (among these, alkyl groups having 3 to 20 carbon atoms may be linear, branched, or cyclic), and it is even more preferable that each independently represent an alkyl group having a total of 1 to 6 carbon atoms which may have a substituent (among these, alkyl groups having 3 to 6 carbon atoms may be linear, branched, or cyclic).

[0041] Also, R ６ ~R ８ When is an alkyl group having a substituent, examples of the substituent include an alkoxy group having 1 to 6 carbon atoms, an aryl group having 1 to 20 carbon atoms, a hydroxy group, an amino group, an alkyl ether group, an aryl ether group, a thiol group, an alkyl sulfide group, or a carboxyl group, and more preferably an alkyl group having a hydroxy group such as a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, or a 2,3-dihydroxypropyl group.

[0042] Here, the alkyl group having a total of 1 to 40 carbon atoms which may have a substituent, or the alkyl group having a total of 1 to 20 carbon atoms which may have a substituent, is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, an octyl group, a decyl group, a hexadecyl group, an octadecyl group, an oleyl group, a 2-ethylhexyl group, a dimethylstearyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 2,3-dihydroxypropyl group, a methoxymethyl group, an ethoxymethyl group, a hydroxyethoxyethyl group, a hydroxyethoxyethoxyethyl group, a benzyl group, a phenethyl group, and an aminoethyl group.

[0043] The alkyl group having a total of 1 to 6 carbon atoms which may have a substituent is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 2,3-dihydroxypropyl group, a methoxymethyl group, an ethoxymethyl group, a hydroxyethoxyethyl group, and a hydroxyethoxyethoxyethyl group.

[0044] Of these, R ６ ~R ８ More preferably, each independently is a methyl group, an ethyl group, an octyl group, a decyl group, a hexadecyl group, an octadecyl group, an oleyl group, a 2-ethylhexyl group, a dimethylstearyl group, or a hydroxyethyl group.

[0045] The pyridine compound is not particularly limited, but examples thereof include pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, picoline, lutidine, etc. Among these, pyridine, picoline, lutidine, etc. are preferred in terms of excellent dispersibility in adhesives, resins, release agents, etc.

[0046] The imidazole compound is not particularly limited, but examples thereof include imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-methylimidazole, 1,2-dimethylimidazole, etc. Among these, imidazole, 1-methylimidazole, 1,2-dimethylimidazole, etc. are preferred in terms of excellent dispersibility in adhesives, resins, release agents, etc.

[0047] The conjugate acid of the amine compound is not particularly limited, but may be, for example, a conjugate acid of an amine compound having a total carbon number of 1 to 50. In terms of excellent dispersibility in adhesives, resins, release agents, etc., it is preferable that the conjugate acid has a total carbon number of 3 to 50, more preferably a conjugate acid of an amine compound having a total carbon number of 4 to 40, and even more preferably a conjugate acid of an amine compound having a total carbon number of 5 to 36.

[0048] More specifically, examples of the conjugate acid of the amine compound include methylammonium ion, dimethylammonium ion, trimethylammonium ion, ethylammonium ion, triethylammonium ion, normal propylammonium ion, isopropylammonium ion, normal butylammonium ion, pentylammonium ion, hexylammonium ion, dimethylisopropylammonium ion, dimethylbutylammonium ion, diethylmethylammonium ion, heptylammonium ion, diisopropylmethylammonium ion, 2-hydroxyethylammonium ion, N,N-dimethyl-N-(2-hydroxyethyl)ammonium ion, N-methyl-N-(2-hydroxyethyl)ammonium ion, di(2-hydroxyethyl)ammonium ion, N-methyl-N,N-di(2-hydroxyethyl)ammonium ion, N,N,N-tri(2-hydroxyethyl)ammonium ion, 2,3-dihydroxypropylammonium ion, N-methyl-N-(2,3-dihydroxypropyl)ammonium ion, N,N-dimethyl-N-(2,3-dihydroxypropyl)ammonium ion, 1,4-butanediammonium ion, triisobutylammonium ion, triisopentylammonium ion, triisooctylammonium ion, octylammonium ion, dioctylammonium ion, 2-ethylhexylammonium ion, diisopropylethylammonium ion, decylammonium ion, dodecylammonium ion, tridecylammonium ion, pentadecylammonium ion, hexadecylammonium ion, octadecylammonium ion, oleylammonium ion, di-n-octylammonium ion, bis(2-ethylhexyl)ammonium ion, dimethyloctylammonium ion, dimethyldecylammonium ion , dimethyldodecylammonium ion, dimethylstearylammonium ion, trihexylammonium ion, trioctylammonium ion, tris(2-ethylhexyl)ammonium ion, phenylammonium ion, pyridinium ion, 2-methylpyridinium ion, 3-methylpyridinium ion, 4-methylpyridinium ion, picolinium ion, lutidinium ion, imidazolium ion, 2-methylimidazolium ion, 2-ethyl-4-methylimidazolium ion, 2-phenylimidazolium ion, 2-phenyl-4-methylimidazolium ion, 1-methylimidazolium ion, or 1,2-dimethylimidazolium ion.

[0049] Among these, the conjugate acids of the above-mentioned amine compounds are preferably pentylammonium ion, dimethylisopropylammonium ion, diethylmethylammonium ion, dimethylbutylammonium ion, hexylammonium ion, triethylammonium ion, heptylammonium ion, diisopropylmethylammonium ion, octylammonium ion, dioctylammonium ion, 2-ethylhexylammonium ion, diisopropylethylammonium ion, decylammonium ion, dodecylammonium ion, tridecylammonium ion, pentadecylammonium ion, hexadecylammonium ion, and the like, because of their excellent dispersibility in adhesives, resins, release agents, and the like. and at least one selected from the group consisting of an ammonium ion, an octadecylammonium ion, an oleylammonium ion, a di-n-octylammonium ion, a bis(2-ethylhexyl)ammonium ion, a dimethyloctylammonium ion, a dimethyldecylammonium ion, a dimethyldodecylammonium ion, a dimethylstearylammonium ion, a trihexylammonium ion, a trioctylammonium ion, a tris(2-ethylhexyl)ammonium ion, a phenylammonium ion, a pyridinium ion, a picolinium ion, a lutidinium ion, an imidazolium ion, a 1-methylimidazolium ion, and a 1,2-dimethylimidazolium ion.

[0050] The quaternary ammonium ion is not particularly limited, but may be, for example, a quaternary ammonium ion having a total carbon number of 1 to 50. In terms of excellent dispersibility in adhesives, resins, release agents, etc., a quaternary ammonium ion having a total carbon number of 3 to 50 is preferred, a quaternary ammonium ion having a total carbon number of 4 to 40 is more preferred, and a quaternary ammonium ion having a total carbon number of 5 to 36 is even more preferred.

[0051] The quaternary ammonium ion is not particularly limited, but examples thereof include a tetramethylammonium ion, a tetraethylammonium ion, a tetra-normal-propylammonium ion, a tetra-normal-butylammonium ion, a tetra-normal-hexylammonium ion, a decyltrimethylammonium ion, a dodecyltrimethylammonium ion, and a tetrahexylammonium ion.

[0052] Among these, at least one selected from the group consisting of decyltrimethylammonium ion, dodecyltrimethylammonium ion, and tetrahexylammonium ion is preferred in terms of excellent dispersibility in adhesives, resins, release agents, etc.

[0053] The above M ＋ Regarding (a), in view of excellent dispersibility in adhesives, resins, release agents, etc., it is preferable that the cation is a hydrogen ion, a conjugate acid of an amine compound having a total of 5 to 36 carbon atoms, or a quaternary ammonium ion having a total of 5 to 36 carbon atoms.

[0054] In addition, the above M ＋ is preferably at least one selected from the group consisting of dioctylammonium ion, tridecylammonium ion, hexadecylammonium ion, octadecylammonium ion, oleylammonium ion, di-n-octylammonium ion, bis(2-ethylhexyl)ammonium ion, dimethylstearylammonium ion, trihexylammonium ion, trioctylammonium ion, tris(2-ethylhexyl)ammonium ion, dodecyltrimethylammonium ion, and tetrahexylammonium ion, in terms of excellent dispersibility in adhesives, resins, release agents, and the like.

[0055] In the above general formulas (3) and (4), m represents an integer of 1 to 10, and n represents 0 or 1.

[0056] Regarding m in the above general formulas (3) and (4), in terms of excellent dispersibility in adhesives, resins, release agents, etc., it is preferably an integer of 2 to 6, more preferably 2, 3, 4, or 5, and even more preferably 2 or 3.

[0057] In addition, n in the general formulas (3) and (4) is preferably 1 in terms of excellent dispersibility in adhesives, resins, release agents, and the like.

[0058] The polythiophene (A) containing at least two or more structural units selected from the group consisting of the structural unit represented by the general formula (3) and the structural unit represented by the general formula (4) has a polystyrene sulfonic acid-equivalent number average molecular weight, as measured by gel permeation chromatography, of preferably 3,500 or more, more preferably 4,000 or more, and even more preferably 5,000 or more, in terms of excellent dispersibility in adhesives, resins, release agents, and the like.

[0059] In terms of ease of handling of the conductive polymer composition, the polythiophene (A) has a number average molecular weight, measured by gel permeation chromatography, reduced to polystyrene sulfonic acid of preferably 30,000 or less, more preferably 20,000 or less, and even more preferably 15,000 or less.

[0060] Therefore, the number average molecular weight of the polythiophene (A) in terms of polystyrene sulfonic acid is preferably 3,500 to 30,000, more preferably 4,000 to 20,000, and even more preferably 5,000 to 15,000.

[0061] The method and conditions for measuring the molecular weight of the polythiophene (A) by gel permeation chromatography are in accordance with ISO 16014-3:2012 (JIS K 7252-3:2016).

[0062] Polythiophene (A) containing at least two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the above general formula (1) and a structural unit represented by the following general formula (2), or polythiophene (A) containing at least two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the above general formula (3) and a structural unit represented by the following general formula (4), can be produced by a known production method.

[0063] In one embodiment of the present invention, the polyether compound (B) is a compound represented by the following general formula (16).

[0064] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0065] R ５ The hydrocarbon group having 1 to 22 carbon atoms in the formula (I) may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.

[0066] R ５The hydrocarbon group having 1 to 22 carbon atoms in the formula (I) is not particularly limited, but examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a decyl group, a dodecyl group, a lauryl group, a hexadecyl group, a palmityl group, an octadecyl group, a stearyl group, an oleyl group, an eicosapentadienyl group, a docosahexaenyl group, a vinyl group, an allyl group, and an oleyl group.

[0067] Of these, R ５ is preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, more preferably a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 5 carbon atoms, or an aliphatic unsaturated hydrocarbon group having 1 to 5 carbon atoms, and still more preferably a hydrogen atom or an aliphatic saturated hydrocarbon group having 1 to 5 carbon atoms.

[0068] In the general formula (16), h is preferably 0 to 20 in terms of improving dispersibility.

[0069] In the general formula (16), k is preferably 0 to 20 in terms of improving dispersibility.

[0070] In the general formula (16), j is preferably 0 to 20 in terms of improving dispersibility.

[0071] In general formula (16), h+i+j preferably satisfies 3≦h+i+j≦50, more preferably 5≦h+i+j≦40, and even more preferably 10≦h+i+j≦30, in terms of improving dispersibility.

[0072] That is, in the general formula (16), X is, in view of availability, each independently k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ Preferably, the divalent polymeric group is formed by random polymerization or block polymerization in random order with aryl, aryl, aryl- ...

[0073] In general formula (16), m is preferably 1 to 5, more preferably 1 to 4, more preferably 1 to 3, and most preferably 1, from the viewpoint of improving dispersibility.

[0074] The conductive polymer composition according to one embodiment of the present invention preferably further contains an organic solvent (C) in that this can improve operability in producing a conductive adhesive film or a conductive release layer.

[0075] In one embodiment of the present invention, the organic solvent (C) can be at least one selected from the group consisting of alcohol-based solvents, glycol ether-based solvents, ether-based solvents, ketone-based solvents, ester-based solvents, amide-based solvents, and aromatic hydrocarbon-based solvents.

[0076] The alcohol solvent is not particularly limited, but examples thereof include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, tertiary butanol, and 1-pentanol.

[0077] The glycol ether solvent is not particularly limited, but examples thereof include ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether propionate, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dibutyl ether, and diethylene glycol monohexyl ether.

[0078] The ether solvent is not particularly limited, but examples thereof include dimethyl ether, diethyl ether, diisopropyl ether, ditertiary butyl ether, tertiary butyl methyl ether, cyclopentyl methyl ether, dicyclohexyl ether, diphenyl ether, and anisole.

[0079] The ester solvent is not particularly limited, but examples thereof include methyl acetate, ethyl acetate, normal propyl acetate, isopropyl acetate, normal butyl acetate, isobutyl acetate, methoxybutyl acetate, γ-butyrolactone, γ-valerolactone, γ-nonalactone, δ-valerolactone, ε-caprolactone, and α-acetyl-γ-butyrolactone.

[0080] The ketone solvent is not particularly limited, but examples thereof include acetone, 2-butanone (methyl ethyl ketone), methyl isobutyl ketone, cyclopentanone, cyclohexanone, acetylacetone, and acetophenone.

[0081] The amide solvent is not particularly limited, but examples thereof include N-methylformamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylimidazole, N,N-dimethylimidazolidinone, and dimethyl sulfoxide.

[0082] The aromatic hydrocarbon solvent is not particularly limited, but examples thereof include benzene, toluene, and xylene.

[0083] The organic solvent (C) is preferably at least one selected from the group consisting of 2-butanone (methyl ethyl ketone), ethyl acetate, butyl acetate, toluene, γ-butyrolactone, and N-methylformamide, in terms of excellent dispersibility in adhesives, resins, release agents, and the like.

[0084] Furthermore, by including a highly polar solvent such as γ-butyrolactone or N-methylformamide as the whole or part of the organic solvent (C), compatibility with pressure-sensitive adhesives of various polarities may be improved.

[0085] With regard to the conductive polymer composition according to one embodiment of the present invention, from the viewpoint of producing a conductive pressure-sensitive adhesive, a conductive resin composition, or a conductive release agent by mixing the conductive polymer composition with a pressure-sensitive adhesive (D), an ultraviolet-curable resin (E), or a release agent (F) described below, the content of the organic solvent (C) is preferably 80 to 99.9 mass%, and more preferably 90 to 99.9 mass%, relative to 100 mass% of the total of the polythiophene (A), the polyether-based compound (B), and the organic solvent (C).

[0086] In the conductive polymer composition according to one embodiment of the present invention, from the viewpoint of improving conductivity, the content of the polythiophene (A) is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and still more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the organic solvent (C).

[0087] In the conductive polymer composition according to one embodiment of the present invention, the content of the polyether compound (B) is preferably 0.01 to 50 parts by mass, more preferably 0.01 to 20 parts by mass, still more preferably 0.05 to 20 parts by mass, and still more preferably 0.1 to 10 parts by mass, relative to 100 parts by mass of the organic solvent (C), in order to provide excellent dispersibility in the pressure-sensitive adhesive (D), the ultraviolet-curable resin (E), the release agent (F), or the like.

[0088] Furthermore, the conductive polymer composition according to one embodiment of the present invention may contain components other than those described above. The components other than those described above are not particularly limited, but examples thereof include a binder and a surfactant.

[0089] The binder is not particularly limited, but examples thereof include cellulose-based resins, vinylpyrrolidone resins, acrylic resins, urethane resins, methyl methacrylate resins, styrene-butadiene resins, vinyl acetate resins, polyamide resins, phenolic resins, epoxy resins, melamine resins, thermosetting polyimides, nitrocellulose, and polyvinyl alcohol resins.

[0090] The binder resin is preferably at least one selected from the group consisting of cellulose resins, vinylpyrrolidone resins, urethane resins, acrylic resins, and epoxy resins, in view of their excellent film-forming properties.

[0091] When the conductive polymer composition according to one embodiment of the present invention contains the binder, the content of the binder is preferably 0.01 to 20 parts by mass, and more preferably 0.1 to 10 parts by mass, relative to 100 parts by mass of the total of the polythiophene (A), the polyether-based compound (B), and the organic solvent (C).

[0092] The surfactant is not particularly limited, but examples thereof include anionic surfactants (e.g., sodium lauryl alcohol sulfate and sodium dodecylbenzenesulfonate), cationic surfactants (e.g., dodecyltrimethylammonium chloride), nonionic surfactants, amphoteric surfactants, fluorine-based surfactants, and silicone-based surfactants, and more preferably at least one selected from the group consisting of nonionic surfactants and amphoteric surfactants.

[0093] The surfactant is not particularly limited, but examples thereof include Ajisper PB821, Ajisper PB822, Ajisper PB824, Ajisper PB881, Ajisper PN411, and Ajisper PA111 manufactured by Ajinomoto Fine-Techno Co., Inc., and Nonion S-40, Nonion K-220, Nonion ST-221, Nonion E-215, Nonion S-4, Nonion O-3, Nonion K-204, Nonion E-202, Nymeen L-202, Nymeen L-207, Uniox MM-400, and Uniox MM-2350 manufactured by NOF Corporation. These surfactants may be used alone, or two or more types may be mixed.

[0094] When the conductive polymer composition according to one embodiment of the present invention contains the surfactant, the content of the surfactant is preferably 0.1 to 60 parts by mass, and more preferably 1 to 40 parts by mass, relative to 100 parts by mass of the total of the polythiophene (A), the polyether-based compound (B), and the organic solvent (C).

[0095] The method for producing the conductive polymer composition according to this embodiment is not particularly limited, but may include, for example, a method in which a composition or solid of the polythiophene (A) according to this embodiment, a polyether compound (B), and an organic solvent (C) are mixed and homogenized by stirring, etc. During the mixing, a binder and / or a surfactant may be added as necessary.

[0096] The temperature during mixing is not particularly limited, but can be, for example, room temperature to heated. Preferably, it may be 0°C or higher and 100°C or lower. The atmosphere during mixing is not particularly limited, but it may be air or an inert gas atmosphere. In this specification, room temperature means 15 to 25°C.

[0097] A conductive pressure-sensitive adhesive according to one embodiment of the present invention is characterized by comprising the conductive polymer composition and a pressure-sensitive adhesive (D). That is, the conductive pressure-sensitive adhesive according to one embodiment of the present invention is characterized by comprising the polythiophene (A), the polyether-based compound (B), and the pressure-sensitive adhesive (D), and preferably further comprises the organic solvent (C). The conductive pressure-sensitive adhesive can also be referred to as a conductive pressure-sensitive adhesive composition.

[0098] The pressure-sensitive adhesive (D) is not particularly limited, but examples thereof include acrylic pressure-sensitive adhesives, silicone pressure-sensitive adhesives, urethane pressure-sensitive adhesives, and rubber pressure-sensitive adhesives.

[0099] Acrylic adhesives refer to adhesives whose main component is acrylic polymer. Silicone adhesives refer to adhesives whose main component is a polymer with a siloxane bond as the main skeleton. Urethane adhesives refer to adhesives whose main component is polyurethane obtained by condensing compounds having an isocyanate group and a hydroxyl group. Rubber adhesives refer to adhesives whose main component is natural rubber or synthetic rubber.

[0100] Among these pressure-sensitive adhesives (D), acrylic pressure-sensitive adhesives are preferred because of their excellent adhesive properties for optical members. The acrylic pressure-sensitive adhesive may be synthesized by the manufacturer or may be a commercially available product. Examples of commercially available products include Arontack pressure-sensitive adhesive manufactured by Toagosei Co., Ltd., Saivinol pressure-sensitive adhesive manufactured by Saiden Chemical Industries, Ltd., and AS pressure-sensitive adhesive manufactured by Lion Specialty Chemicals.

[0101] Specific trade names of the Arontack pressure sensitive adhesive include Arontack S-1601, Arontack S-1605, Arontack S-1511X, Arontack S-1511 modified, Arontack S-3403, and Arontack S-3452YKF. Examples of Saivinol adhesives include Saivinol AT-245, Saivinol AT-191, Saivinol ATR-340, Saivinol AT-D37L, Saivinol AT-211, Saivinol AT-262, Saivinol AT-197, Saivinol AT-193, Saivinol ATR-1, Saivinol ATR-373, Saivinol ATR-347, Saivinol ATR-300, Saivinol AT-420NT, Saivinol AT-422NT, Saivinol AT-260NT, Saivinol AT-D54, Saivinol AT-352, Saivinol AT-D50, Saivinol AT-D40, Saivinol AT-D37, and Saivinol AT-D45. Examples of AS adhesives include AS-4005 and AS-455. As the pressure-sensitive adhesive (D), these pressure-sensitive adhesives may be used alone or in combination of two or more kinds.

[0102] The pressure-sensitive adhesive (D) may also contain a curing agent (crosslinking agent). Examples of the crosslinking agent include, but are not limited to, isocyanate compounds, epoxy compounds, memine resins, aziridine derivatives, and metal chelate compounds. These crosslinking agents may be used alone or in combination.

[0103] In the conductive pressure-sensitive adhesive according to one embodiment of the present invention, from the viewpoint of improving conductivity, the content of polythiophene (A) is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and even more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the pressure-sensitive adhesive (D).

[0104] In the conductive pressure-sensitive adhesive according to one embodiment of the present invention, the content of the polyether compound (B) is preferably 0.01 to 15 parts by mass, more preferably 0.05 to 8 parts by mass, and even more preferably 0.1 to 6 parts by mass, relative to 100 parts by mass of the pressure-sensitive adhesive (D), in terms of excellent dispersibility of the polythiophene (A).

[0105] In the conductive adhesive according to one embodiment of the present invention, from the viewpoint of operability such as coatability, the concentration of the organic solvent (C) is preferably 20 to 80 mass %, more preferably 30 to 70 mass %, and even more preferably 40 to 60 mass %, with the entire conductive adhesive being taken as 100 mass %.

[0106] The conductive adhesive film according to one embodiment of the present invention is not particularly limited, and can be produced, for example, by a production method including a step of applying the conductive adhesive according to one embodiment of the present invention to a substrate to produce a coating film, and a step of heating the coating film. The conductive adhesive film produced in this manner is characterized by including the above-mentioned polythiophene (A), the above-mentioned polyether compound (B), and the above-mentioned adhesive (D).

[0107] The substrate is not particularly limited, but examples thereof include glass, plastic, polyester, polyacrylate, polycarbonate, and resist substrates.

[0108] The application method is not particularly limited, but examples thereof include screen printing, casting, dipping, bar coating, roll coating, gravure coating, flexographic printing, spray coating, and inkjet printing.

[0109] The heating temperature is not particularly limited as long as it is a temperature at which a uniform conductive adhesive film can be obtained and is equal to or lower than the heat resistance temperature of the substrate, but is preferably in the range of room temperature (15 to 25°C) to 300°C, more preferably in the range of room temperature to 250°C, and even more preferably in the range of 90 to 250°C.

[0110] The heating atmosphere may be any of air, inert gas, vacuum, and reduced pressure. From the viewpoint of suppressing deterioration of the conductive adhesive film, an inert gas atmosphere such as nitrogen or argon is preferred.

[0111] The thickness of the conductive adhesive film according to one embodiment of the present invention is not particularly limited, but is preferably 1×10 －２ ~1 x 10 ２ The range of μm is preferred.

[0112] According to the above-described production method, a conductive adhesive film having good antistatic properties can be obtained. The antistatic properties of the conductive adhesive film can be evaluated, for example, by surface resistivity.

[0113] As described above, the conductive polymer composition has excellent dispersibility in adhesives (D), ultraviolet-curable resins (E), release agents (F), etc., and exhibits the effect of being able to provide a conductive adhesive film with excellent antistatic properties. Furthermore, the conductive polymer composition is not limited to this, and also has excellent dispersibility in ultraviolet-curable resins, and exhibits the effect of being able to provide a conductive hard coat film (also simply referred to as a "conductive hard coat") with excellent antistatic properties. Furthermore, the conductive polymer composition has excellent dispersibility in release agents, and exhibits the effect of being able to provide a conductive release layer with excellent antistatic properties.

[0114] A conductive resin composition according to one embodiment of the present invention is characterized by containing the conductive polymer composition and an ultraviolet-curable resin (E). That is, the conductive resin composition according to one embodiment of the present invention is characterized by containing the polythiophene (A), the polyether compound (B), and the ultraviolet-curable resin (E), and preferably further contains the organic solvent (C).

[0115] The ultraviolet-curable resin (E) may be any known resin, and is not particularly limited. Generally, the ultraviolet-curable resin (E) may contain an oligomer (e1), a monomer (e2), a photopolymerization initiator (e3), and the like.

[0116] The oligomer (e1) is not particularly limited, and examples thereof include urethane (meth)acrylate oligomers, epoxy (meth)acrylate oligomers, polyester (meth)acrylate oligomers, and (meth)acrylic (meth)acrylate oligomers. These oligomers (e1) may be used alone or in combination of two or more. Among these, from the viewpoint of improving the hardness of the conductive hard coat, it is preferable to use at least one selected from the group consisting of urethane (meth)acrylate oligomers and epoxy (meth)acrylate oligomers. The oligomer (e1) preferably contains a (meth)acrylate oligomer having 15 or fewer functionalities (i.e., the number of (meth)acrylic groups in the oligomer is 15 or fewer), and more preferably contains a (meth)acrylate oligomer having 10 or fewer functionalities.

[0117] Examples of the oligomer (e1) include trade names: UA-1100H (Shin-Nakamura Chemical Co., Ltd.), trade name: UN-904 (Negami Chemical Industries Co., Ltd.), trade name: RUA-071 (Asia Industries Co., Ltd.), trade name: RUA-076MG (Asia Industries Co., Ltd.), trade name: EBECRYL 600 (Daicel Allnex Co., Ltd.), trade name: X-40-2669 (Shin-Etsu Silicones), KR-470 (Shin-Etsu Silicones), etc. These may be used alone or in combination of two or more.

[0118] The monomer (e2) is not particularly limited, but examples thereof include acrylate monomers, methacrylate monomers, and (meth)acrylsilane monomers, and more specifically, examples thereof include 2-hydroxyethyl acrylate, isobornyl acrylate, pentaerythritol tetraacrylate, 4-acryloylmorpholine, glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetraacrylate, diethylene glycol diacrylate, diethylene glycol diacrylate, ethylene glycol monomethyl ether acrylate, ethylene glycol monoacrylate, 1,3-propanediol diacrylate, glycerol trimethacrylate, and 1,3-propanediol dimethacrylate. These monomers (e2) may be used alone or in combination of two or more. Among these, at least one selected from the group consisting of acrylate monomers and methacrylate monomers is preferred, and from the viewpoint of improving the compatibility of the composition, 2-hydroxyethyl acrylate, isobornyl acrylate, or 4-acryloylmorpholine is more preferred.

[0119] The photopolymerization initiator (e3) can be any photopolymerization initiator used in the relevant field without any limitation, and examples thereof include 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-(dimethylamino)-1-[4-(morpholino)phenyl]-1-butanone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2,2-dimethoxy-2-phenylacetophenone, and 2-hydroxy-2-methylpropiophenone.

[0120] The ultraviolet-curable resin (E) preferably contains at least an oligomer (e1), more preferably contains an oligomer (e1) and a monomer (e2), and even more preferably contains an oligomer (e1), a monomer (e2), and a photopolymerization initiator (e3).

[0121] The conductive resin composition according to one embodiment of the present invention contains the polythiophene (A), the polyether compound (B), and the ultraviolet-curable resin (E), and preferably contains the organic solvent (C). The organic solvent (C) contained in the conductive resin composition is preferably an alcohol-based solvent, an ester-based solvent, a glycol ether-based solvent, or an aromatic hydrocarbon-based solvent, in terms of excellent operability in forming a coating film for producing a conductive hard coat, and more preferably ethanol, ethyl acetate, butyl acetate, toluene, or 1-methoxy-2-propanol (PGME).

[0122] The content of the ultraviolet curable resin (E) in the conductive resin composition according to one embodiment of the present invention is not limited, but is preferably 10 to 80 mass %, and more preferably 10 to 60 mass %, with the entire conductive resin composition being 100 mass %.

[0123] The content of the oligomer (e1) in the conductive resin composition according to one embodiment of the present invention is not limited, but is preferably 5 to 80 mass %, more preferably 5 to 60 mass %, more preferably 5 to 40 mass %, and even more preferably 5 to 30 mass %, based on 100 mass % of the entire conductive resin composition.

[0124] The content of the monomer (e2) in the conductive resin composition according to one embodiment of the present invention is not limited, but is preferably 10 to 80 mass%, more preferably 10 to 60 mass%, and still more preferably 10 to 40 mass%, with the entire conductive resin composition being 100 mass%.

[0125] The content of the photopolymerization initiator (e3) in the conductive resin composition according to one embodiment of the present invention is not limited, but is preferably 0.1 to 10 mass%, more preferably 0.2 to 8 mass%, and still more preferably 0.5 to 5 mass%, based on 100 mass% of the entire conductive resin composition.

[0126] The content of the photopolymerization initiator (e3) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and still more preferably 5 to 20 parts by mass, relative to 100 parts by mass of the total amount of the oligomer (e1) and the monomer (e2).

[0127] The conductive hard coat according to one embodiment of the present invention is not particularly limited, but can be produced, for example, by applying the conductive resin composition according to one embodiment of the present invention to a substrate and then irradiating it with ultraviolet light. The conductive hard coat produced in this manner is characterized by containing the above-mentioned polythiophene (A) and the above-mentioned polyether-based compound (B).

[0128] The substrate is not particularly limited, but examples thereof include glass, plastic, polyester, polyacrylate, polycarbonate, and resist substrates.

[0129] The application method is not particularly limited, but examples thereof include screen printing, casting, dipping, bar coating, roll coating, gravure coating, flexographic printing, spray coating, and inkjet printing.

[0130] The conductive resin composition according to one embodiment of the present invention is not particularly limited, but for example, is cured by irradiation with deep ultraviolet light having a wavelength of 250 to 320 nm to produce a conductive hard coat.

[0131] The ultraviolet light source is not particularly limited, but examples thereof include a mercury lamp, a short-wavelength light-emitting diode, an ultraviolet excimer fluorescent lamp, an electron beam excited light-emitting lamp, a microplasma excited light-emitting lamp, and an organic EL.

[0132] The wavelength, irradiation intensity, and integrated light amount of the ultraviolet light are appropriately adjusted depending on the type and amount of the ultraviolet-curable resin (E) contained in the conductive resin composition, the type and amount of the photoradical initiator, and the desired shape, such as thickness and size, of the conductive hard coat.

[0133] The ultraviolet irradiation atmosphere may be any of air, inert gas, vacuum, and reduced pressure. From the viewpoint of suppressing deterioration of the conductive hard coat, an inert gas atmosphere such as nitrogen or argon is preferred.

[0134] The thickness of the conductive hard coat according to one embodiment of the present invention is not particularly limited, but is preferably 1×10 －２ ~1 x 10 ２ The range of μm is preferred.

[0135] According to the above-described production method, a conductive hard coat having good antistatic properties can be obtained. The antistatic properties of the conductive hard coat can be evaluated, for example, by the surface resistivity.

[0136] A conductive release agent according to one embodiment of the present invention comprises the conductive polymer composition and a release agent (F). That is, the conductive release agent according to one embodiment of the present invention comprises the polythiophene (A), the polyether compound (B), the organic solvent (C), and the release agent (F). The conductive release agent can also be referred to as a conductive release agent composition.

[0137] The release agent (F) is not particularly limited, but examples thereof include wax-based release agents, silicone-based release agents, and fluorine-based release agents.

[0138] The wax-based release agent is not particularly limited, but examples thereof include carnauba wax (vegetable wax), wool wax (animal wax), paraffin wax, polyethylene wax, and oxidized polyethylene wax.

[0139] The silicone-based release agent is not particularly limited, but examples thereof include silicone oil, silicone wax, silicone resin, and polyorganosiloxane having a polyoxyalkylene unit.

[0140] The fluorine-based release agent is not particularly limited, but examples thereof include fluorine oil and polytetrafluoroethylene.

[0141] The content of the release agent (F) in the conductive release agent according to one embodiment of the present invention is not limited, but is preferably 10 to 80% by mass, and more preferably 10 to 60% by mass, with the entire conductive release agent being taken as 100% by mass.

[0142] The conductive release layer according to one embodiment of the present invention is not particularly limited, but can be produced, for example, by applying the conductive release agent according to one embodiment of the present invention to a substrate and then drying it. The conductive release layer produced in this manner is characterized by containing the above-mentioned polythiophene (A), the above-mentioned polyether compound (B), and the release agent (F).

[0143] The substrate is not particularly limited, but examples thereof include glass, plastic, polyester, polyacrylate, polycarbonate, and resist substrates.

[0144] The application method is not particularly limited, but examples thereof include screen printing, casting, dipping, bar coating, roll coating, gravure coating, flexographic printing, spray coating, and inkjet printing.

[0145] The drying temperature is not particularly limited as long as it is a temperature at which a uniformly dried conductive adhesive film is obtained and is equal to or lower than the heat resistance temperature of the substrate, but is preferably in the range of room temperature (15 to 25°C) to 300°C, more preferably in the range of room temperature to 250°C, and even more preferably in the range of 90 to 250°C.

[0146] The drying atmosphere may be air, an inert gas, a vacuum, or a reduced pressure. From the viewpoint of preventing deterioration of the conductive adhesive film, an inert gas such as nitrogen or argon is preferred.

[0147] The thickness of the conductive release layer according to one embodiment of the present invention is not particularly limited, but is preferably 1×10 －２ ~1 x 10 ２ The range of μm is preferred.

[0148] According to the above-described production method, a conductive release layer having good antistatic properties can be obtained. The antistatic properties of the conductive release layer can be evaluated, for example, by the surface resistivity.

[0149] [Summary] As a result of extensive investigations, the present inventors have found that the invention described below can solve the problems of the present invention, and have completed the present invention.

[0150] [1] A conductive polymer composition comprising: a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether-based compound (B) represented by the following general formula (16):

[0151] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0152] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0153] [2] The conductive polymer composition according to [1], wherein the polythiophene (A) is a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (3) and a structural unit represented by the following general formula (4):

[0154] [In the general formula (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium ion. ２ represents a hydrogen atom, a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 6 carbon atoms, or a fluorine atom; m represents an integer of 1 to 10; and n represents 0 or 1.

[0155] [3] Said M ＋ is a hydrogen ion, a conjugate acid of an amine compound having a total of 5 to 36 carbon atoms, or a quaternary ammonium ion having a total of 5 to 36 carbon atoms.

[0156] [4] Said M ＋ is at least one selected from the group consisting of a dioctylammonium ion, a tridecylammonium ion, a hexadecylammonium ion, an octadecylammonium ion, an oleylammonium ion, a di-n-octylammonium ion, a bis(2-ethylhexyl)ammonium ion, a dimethylstearylammonium ion, a trihexylammonium ion, a trioctylammonium ion, a tris(2-ethylhexyl)ammonium ion, a dodecyltrimethylammonium ion, and a tetrahexylammonium ion.

[0157] [5] The conductive polymer composition according to any one of [1] to [4], wherein n is 1 in the general formula (16).

[0158] [6] The conductive polymer composition according to any one of [1] to [5], further comprising an organic solvent (C).

[0159] [7] The conductive polymer composition according to [6], wherein the organic solvent (C) is at least one selected from the group consisting of alcohols, glycol ethers, ethers, ketones, esters, amides, and aromatic hydrocarbons.

[0160] [8] The conductive polymer composition according to [6] or [7], wherein the content of the polythiophene (A) is 0.01 to 10 parts by mass per 100 parts by mass of the organic solvent (C).

[0161] [9] The conductive polymer composition according to any one of [6] to [8], wherein the content of the polyether compound (B) is 0.01 to 20 parts by mass per 100 parts by mass of the organic solvent (C).

[0162]

[10] A conductive pressure-sensitive adhesive comprising the conductive polymer composition according to any one of [1] to [9] and a pressure-sensitive adhesive (D).

[0163]

[11] The conductive pressure-sensitive adhesive according to

[10] , wherein the pressure-sensitive adhesive (D) is an acrylic pressure-sensitive adhesive.

[0164]

[12] A method for producing a conductive adhesive film, comprising the steps of applying the conductive adhesive according to

[10] or

[11] to a substrate to produce a coating film, and heating the coating film.

[0165]

[13] A conductive adhesive film comprising: a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); a polyether compound (B) represented by the following general formula (16); and an adhesive (D).

[0166] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0167] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0168]

[14] A conductive resin composition comprising the conductive polymer composition according to any one of [1] to [9] and an ultraviolet-curable resin (E).

[0169]

[15] A method for producing a conductive hard coat, comprising applying the conductive resin composition according to

[14] to a substrate and irradiating the substrate with ultraviolet light.

[0170]

[16] A conductive hard coat comprising: a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether compound (B) represented by the following general formula (16):

[0171] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0172] [In the general formula (16), R ５Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0173]

[17] A conductive release agent comprising the conductive polymer composition according to any one of [1] to [9] and a release agent (F).

[0174]

[18] A method for producing a conductive release layer, comprising applying the conductive release agent according to

[17] to a substrate and drying it.

[0175]

[19] A conductive release layer comprising: a polythiophene (A) containing two or more structural units of at least one kind selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether compound (B) represented by the following general formula (16):

[0176] [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0177] [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]

[0178] [Notes] The present invention is not limited to the above-described embodiments, and various modifications are possible within the scope of the claims. Embodiments obtained by appropriately combining the technical means disclosed in different embodiments are also included in the technical scope of the present invention.

[0179] Examples of the conductive polymer composition according to one embodiment of the present invention and its applications are shown below, but the present invention is not limited to these examples.

[0180] [Measurement of Particle Diameter of Conductive Polymer Composition] The particle diameter (D50) of the conductive polymer composition was measured using a particle diameter measuring device (UPA-UT151 manufactured by Nikkiso Co., Ltd.).

[0181] [Method for measuring the surface resistance of a conductive adhesive film] A conductive adhesive containing a conductive polymer composition and an adhesive was applied to a poly film using a Select-Roller / A-Bar (manufactured by OSG System Products), and dried at 80°C to produce a conductive adhesive film with a film thickness of 52 µm. The surface resistance of this conductive adhesive film was measured using a high resistivity meter Hiresta (registered trademark)-UX MCP-HT800 (manufactured by Nisshin Seiko Analytech).

[0182] It can be said that the lower the surface resistivity of a conductive adhesive film, the higher the antistatic ability. １３ If the resistance is less than Ω / □, it can be said to be a conductive adhesive film with antistatic properties. １２ It is preferably 10 Ω / □ or less, １１It is more preferable that the resistance is 10 Ω / □ or less, １０ It is more preferable that the resistance is Ω / □ or less.

[0183] [Method for measuring surface resistance of conductive hard coat] A conductive resin composition containing a conductive polymer composition and an ultraviolet-curable resin was applied to a film using a Select-Roller / A-Bar (manufactured by OSG System Products), and dried at 80°C to produce a conductive hard coat with a wet film thickness of 18 µm. The surface resistance of this conductive hard coat was measured using a high resistivity meter, Hiresta (registered trademark)-UX MCP-HT800 (manufactured by Nisshin Seiko Analytech).

[0184] It can be said that the lower the surface resistivity of the conductive hard coat, the higher the antistatic ability. １３ If the resistivity is less than Ω / □, it can be said that the conductive release layer has antistatic properties. １２ It is preferably 10 Ω / □ or less, １１ It is more preferable that the resistance is 10 Ω / □ or less, １０ It is more preferable that the resistance is Ω / □ or less.

[0185] [Method for measuring the surface resistance of a conductive release layer] A conductive release agent containing a conductive polymer composition and a release agent was applied to a film using a Select-Roller / A-Bar (manufactured by OSG System Products), and dried at 120°C to produce a conductive release layer with a wet film thickness of 6 µm. The surface resistance of this conductive release layer was measured using a high resistivity meter Hiresta (registered trademark)-UX MCP-HT800 (manufactured by Nisshin Seiko Analytech).

[0186] It can be said that the lower the surface resistivity of the conductive release layer, the higher the antistatic ability. １３ If the resistivity is less than Ω / □, it can be said that the conductive release layer has antistatic properties. １２ It is preferably 10 Ω / □ or less, １１ It is more preferable that the resistance is 10 Ω / □ or less, １０ It is more preferable that the resistance is Ω / □ or less.

[0187] Synthesis Example 1 Synthesis of polythiophene (A) (PT) According to a conventionally known production method, 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonic acid polymer (a polymer containing repeating units represented by the following formula (5) and the following formula (6) (wherein M ＋ represents a hydrogen ion. ), and a number average molecular weight of about 7000) was produced.

[0188]

[0189] 7.4 g of a methanol solution containing 5 mass % of dioctylamine was stirred with 50.0 g of an aqueous solution containing 1 mass % of the above 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonic acid polymer, and the resulting precipitate was filtered and dried to obtain 0.6 g of a solid of the dioctylammonium salt of the above polymer (which corresponds to the above polythiophene (A) and will hereinafter also be referred to as "PT"). That is, the PT is a dioctylammonium salt of the above polymer represented by the general formula (1) ＋ It contains the conjugate acid of dioctylamine (i.e., dioctylammonium ion) as the cation.

[0190] Production Example of Polyether Compound (B) Polyether compound (17) was synthesized according to the method of Synthesis Example 1 described in JP 2014-147926 A (NOF Corporation). Similarly, polyether compound (18) was synthesized according to the method of Synthesis Example 2, polyether compound (19) according to the method of Synthesis Example 3, and polyether compound (20) according to the method of Synthesis Example 4. Furthermore, polyether compound (21) was synthesized according to the method of Synthesis Example 1 described in JP 2014-205088 A (NOF Corporation). Similarly, polyether compound (22) was synthesized according to the method of Synthesis Example 2.

[0191] The structures of the above polyether compounds (17), (18), (19), (20), (21), and (22) are shown in Table 1. All of these correspond to the polyether compound (B) represented by the above general formula (16).

[0192]

[0193] Example 1 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.2 g of the polyether-based compound (17) as the polyether-based compound (B) were added to 9.7 g of ethyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.1 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0194] Examples 2 to 6 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one embodiment of the present invention were prepared in the same manner as in Example 1, except that 0.2 g of the polyether compound (17) in Example 1 was replaced with 0.2 g of the polyether compound (18), (19), (20), (21), or (22). In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each composition are shown in Table 2.

[0195] Example 7 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.2 g of the polyether-based compound (17) as the polyether-based compound (B) were added to 9.7 g of butyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.1 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0196] Examples 8 to 12 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one embodiment of the present invention were prepared in the same manner as in Example 7, except that 0.2 g of the polyether compound (17) in Example 7 was replaced with 0.2 g of the polyether compound (18), (19), (20), (21), or (22). In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each composition are shown in Table 2.

[0197] Example 13 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.2 g of the polyether-based compound (17) as the polyether-based compound (B) were added to 9.7 g of toluene as the organic solvent (C) and stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Measurement of Particle Diameter of Conductive Polymer Composition," and was found to be 2.0 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0198] Examples 14 to 18 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one embodiment of the present invention were prepared in the same manner as in Example 13, except that 0.2 g of the polyether compound (17) in Example 13 was replaced with 0.2 g of the polyether compound (18), (19), (20), (21), or (22). In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each composition are shown in Table 2.

[0199] Example 19 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.2 g of the polyether-based compound (17) as the polyether-based compound (B) were added to 9.7 g of 2-butanone as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle size of the conductive polymer composition was measured according to the above-mentioned "Particle Size Measurement of Conductive Polymer Composition," and was found to be 2.0 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0200] Examples 20 to 24 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one embodiment of the present invention were prepared in the same manner as in Example 19, except that 0.2 g of the polyether compound (17) in Example 19 was replaced with 0.2 g of the polyether compound (18), (19), (20), (21), or (22). In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each composition are shown in Table 2.

[0201] Example 25 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.2 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 9.7 g of acetone as the organic solvent (C) and stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Measurement of Particle Diameter of Conductive Polymer Composition," and was found to be 2.0 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0202] Examples 26 to 44 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one aspect of the present invention were prepared in the same manner as in Example 25, except that 9.7 g of a solvent or mixed solvent shown in Table 2 was used instead of 9.7 g of acetone. In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each example are shown in Table 3.

[0203] Example 45 (Preparation and Evaluation of Conductive Polymer Composition) 0.01 g of the PT as the polythiophene (A) and 0.02 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 9.97 g of ethyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Measurement of Particle Diameter of Conductive Polymer Composition," and was found to be 2.0 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0204] Example 46 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 1 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 8.9 g of ethyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.1 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0205] Example 47 (Preparation and Evaluation of Conductive Polymer Composition) 0.2 g of the PT as the polythiophene (A) and 0.4 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 9.4 g of ethyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.4 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0206] Example 48 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.05 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 9.85 g of ethyl acetate as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.4 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0207] Example 49 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A) and 0.05 g of the polyether-based compound (18) as the polyether-based compound (B) were added to 9.85 g of 2-butanone as the organic solvent (C), and the mixture was stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition," and was found to be 2.2 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0208] Comparative Example 1 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of PT as the polythiophene (A) was added to 9.9 g of ethyl acetate and stirred to prepare a composition. However, the PT was not uniformly dissolved or dispersed in the composition.

[0209] Comparative Example 2 (Preparation and Evaluation of Conductive Polymer Composition) A composition was prepared by adding 0.1 g of PT as the polythiophene (A) and 0.2 g of polyethylene glycol (PEG-400) (manufactured by Tokyo Chemical Industry Co., Ltd.) to 9.7 g of butyl acetate and stirring the mixture. However, the PT was not uniformly dissolved or dispersed in the composition.

[0210] Comparative Example 3 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of PEDOT:PSS solid (Orgacon DRY, manufactured by ALDRICH) instead of the polythiophene (A) and 0.2 g of the polyether compound (18) were added to 9.7 g of ethyl acetate, and the mixture was stirred to prepare a composition. However, the PEDOT:PSS solid was not uniformly dissolved or dispersed in the composition.

[0211] The compositions and particle size measurement results for each of the above-described Examples and Comparative Examples are shown in Tables 2 and 3. Note that no polyether compound (B) was added in Comparative Example 2. Furthermore, no polythiophene (A) was added in Comparative Example 3. Therefore, in Comparative Examples 2 and 3, the compounds added as substitutes for these compounds are shown in parentheses.

[0212]

[0213]

[0214] Example 151 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A), 0.05 g of the polyether-based compound (18) as the polyether-based compound (B), and 9.85 g of ethanol as the organic solvent (C) were mixed to a total of 10.0 g and stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Measurement of Particle Diameter of Conductive Polymer Composition," and was found to be 1.0 nm. It was found that the PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0215] Example 156 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A), 0.1 g of the polyether compound (18) as the polyether compound (B), 0.1 g of Nymeen L-202 manufactured by NOF Corporation as a surfactant, and 9.7 g of 2-propanol as the organic solvent (C) were mixed to a total of 10.0 g and stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Particle diameter measurement of conductive polymer composition" and found to be 1.0 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0216] Example 158 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A), 0.2 g of the polyether compound (18) as the polyether compound (B), and 1.6 g of γ-butyrolactone, 3.3 g of 2-butanone, and 3.3 g of ethyl acetate as the organic solvent (C) were mixed to a total of 8.5 g, and the mixture was stirred. Then, 0.5 g of a γ-butyrolactone solution of Ajinomoto Fine-Techno Co., Inc.'s Ajisper PB881, which had been adjusted to a solids concentration of 20 wt%, 0.5 g of a γ-butyrolactone solution of Nymeen L-202, which had been adjusted to a solids concentration of 20 wt%, and 0.5 g of a γ-butyrolactone solution of NOF Corporation's Nonion K-220, which had been adjusted to a solids concentration of 20 wt%, were added to the mixture. 0.5 g of the surfactant was mixed and stirred to prepare 10.0 g of a conductive polymer composition according to one embodiment of the present invention. In Table 4 described below, the solvent used for the surfactant is the organic solvent (C), and the composition ratio calculation results are shown. The particle diameter of the conductive polymer composition was measured according to the above-mentioned "Measurement of particle diameter of conductive polymer composition," and was found to be 2.1 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0217] Examples 162, 166, 170, 174, 178, and 182 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one aspect of the present invention were prepared in the same manner as in Example 158, except that the ratio of the surfactant and the ratio of the organic solvent (C) were changed. In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each example are shown in Table 4.

[0218] Example 186 (Preparation and Evaluation of Conductive Polymer Composition) 0.1 g of the PT as the polythiophene (A), 0.05 g of the polyether compound (18) as the polyether compound (B), and 9.85 g of 1-methoxy-2-propanol as the organic solvent (C) were mixed to a total of 10.0 g and stirred to prepare a conductive polymer composition according to one embodiment of the present invention. The particle size of the conductive polymer composition was measured according to the above-mentioned "Particle Size Measurement of Conductive Polymer Composition" and found to be 1.3 nm. It was found that PT was uniformly dissolved or dispersed in the conductive polymer composition.

[0219] Examples 188, 190, and 192 (Preparation and Evaluation of Conductive Polymer Compositions) Conductive polymer compositions according to one embodiment of the present invention were prepared in the same manner as in Example 186, except that the types or ratios of the polyether compound (B) and the organic solvent (C) used in Example 186 were changed. In all cases, it was found that PT was uniformly dissolved or dispersed in the conductive polymer composition. The formulations and measurement results for each example are shown in Table 4.

[0220]

[0221] From the results of the Examples and Comparative Examples, it was confirmed that a conductive polymer composition that is uniformly dissolved or dispersed in an organic solvent (C) can be produced by combining a polythiophene (A) with a polyether-based compound (B) represented by the above general formula (16).

[0222] Example 51 (Preparation and Evaluation of Conductive Adhesive) 2 g of the conductive polymer composition prepared in Example 1 above, 2 g of Saivinol AT-245 (manufactured by Saiden Chemical Industries, Ltd.) as adhesive (D), and 0.04 g of K-901 (manufactured by Saiden Chemical Industries, Ltd.) as a curing agent were mixed and stirred to prepare a conductive adhesive according to one embodiment of the present invention. In the conductive adhesive according to one embodiment of the present invention, the conductive polymer composition exhibited high dispersibility. A conductive adhesive film according to one embodiment of the present invention was produced according to the above [Method for measuring surface resistance of conductive adhesive film], and the surface resistance was measured. The result was 10 １０ The results are shown in Table 5.

[0223] Examples 52 to 99 In Example 51, 2 g of the conductive polymer composition prepared in Example 1 above was replaced with 2 g of the conductive polymer composition prepared in Examples 2 to 49 above, to prepare conductive adhesives according to one embodiment of the present invention. In all conductive adhesives, the conductive polymer composition exhibited high dispersibility. Conductive adhesive films according to one embodiment of the present invention were produced according to the above-mentioned [Method for measuring surface resistance of conductive adhesive film], and the surface resistance was measured. The results are shown in Table 5.

[0224] Comparative Examples 4 to 6 (Preparation and Evaluation of Mixed Solutions Containing Pressure-Sensitive Adhesives) In Example 51, pressure-sensitive adhesive compositions were prepared using 2 g of the compositions prepared in Comparative Examples 1 to 3 instead of 2 g of the conductive polymer composition prepared in Example 1. In all of the pressure-sensitive adhesive compositions, the dispersibility of the conductive material was low. Adhesive films were produced using these pressure-sensitive adhesive compositions according to the above-mentioned [Method for Measuring Surface Resistance of Conductive Adhesive Films], and the surface resistance was measured. The results are shown in Table 5.

[0225]

[0226] (Synthesis of adhesive (d1)) 94 parts by mass of 2-ethylhexyl acrylate (2EHA) as a monomer component, 5 parts by mass of 2-hydroxyethyl acrylate (HEA), 1 part by mass of methacrylic acid (MAA), 0.33 parts by mass of 2,2'-azobisisobutyronitrile as a polymerization initiator, and 96 parts by mass of ethyl acetate as a polymerization solvent were placed in a separable flask and stirred for 1 hour while introducing nitrogen gas (removing oxygen from the polymerization system). Next, the temperature was raised to 67 ° C. and reacted for 10 hours, after which ethyl acetate was added to obtain a solution of adhesive (d1) with a solids concentration of 30% by mass.

[0227] Example 101 (Preparation and Evaluation of Conductive Adhesive) 2 g of the conductive polymer composition prepared in Example 1 above was mixed with 2 g of adhesive (d1) as adhesive (D), and then 0.04 g of Karenz MOI manufactured by Resonac Corporation was added as a curing agent and stirred to prepare a conductive adhesive according to one embodiment of the present invention. In this conductive adhesive, the conductive polymer composition exhibited high dispersibility. A conductive adhesive film according to one embodiment of the present invention was produced according to the above [Method for measuring surface resistance of conductive adhesive film], and the surface resistance was measured. １０ The results are shown in Table 6.

[0228] Examples 102 to 149 In Example 101, 2 g of the conductive polymer composition prepared in Example 1 above was replaced with 2 g of the conductive polymer composition prepared in Examples 2 to 49 above, to prepare conductive adhesives according to one embodiment of the present invention. In all conductive adhesives, the conductive polymer composition exhibited high dispersibility. Conductive adhesive films according to one embodiment of the present invention were produced according to the above-mentioned [Method for measuring surface resistance of conductive adhesive film], and the surface resistance was measured. The results are shown in Table 6.

[0229] Comparative Examples 7 to 9 (Preparation and Evaluation of Mixed Solutions Containing Pressure-Sensitive Adhesives) In Example 101, pressure-sensitive adhesive compositions were prepared using 2 g of the compositions prepared in Comparative Examples 1 to 3 instead of 2 g of the conductive polymer composition prepared in Example 1. In all of the pressure-sensitive adhesive compositions, the dispersibility of the conductive material was low. Adhesive films were produced using these pressure-sensitive adhesive compositions according to the above-mentioned [Method for Measuring Surface Resistance of Conductive Adhesive Films], and the surface resistance was measured. The results are shown in Table 6.

[0230]

[0231] Example 159 (Preparation and Evaluation of Conductive Adhesive) 0.3 g of the conductive polymer composition prepared in Example 158 above was mixed with 0.5 g of AS-4005 (manufactured by Lion Specialty Chemicals) prepared as adhesive (D) with ethyl acetate to a solids concentration of 30%, and 0.5 g of ethyl acetate as organic solvent (C). The mixture was stirred for 1 hour, and then 0.1 g of Tetrad-X (manufactured by Mitsubishi Gas Chemical Company, Inc.) prepared as a curing agent with ethyl acetate to a solids concentration of 10% was mixed to a total of 1.1 g. The mixture was stirred for 1 hour to prepare a conductive adhesive according to one embodiment of the present invention. In this conductive adhesive, the conductive polymer composition exhibited high dispersibility. Using the conductive adhesive one hour after preparation, a conductive adhesive film according to one embodiment of the present invention was produced according to the above-mentioned [Method for Measuring Surface Resistance of Conductive Adhesive Film], and the surface resistance was measured. The result was 10 １０ The results are shown in Table 7.

[0232] Examples 160, 161, 163-165, 167-169, 171-173, 175-177, 179-181, 183-185 (Preparation and Evaluation of Conductive Adhesives) Conductive adhesives according to one embodiment of the present invention were prepared using the conductive polymer compositions prepared in Examples 158, 162, 166, 170, 174, 178, or 182 above, AS-4005, AS-455, or d1 manufactured by Lion Specialty Chemicals Corporation as the adhesive (D), and Tetrad-X manufactured by Mitsubishi Gas Chemical Company, Inc. or Karenz MOI manufactured by Resonac Corporation as the curing agent. In each conductive adhesive, the conductive polymer composition exhibited high dispersibility. Using each of the resulting conductive adhesives, conductive adhesive films according to one embodiment of the present invention were produced according to the above-mentioned "Method for Measuring the Surface Resistance of a Conductive Adhesive Film," and the surface resistance was measured. The formulations and measurement results are shown in Table 7.

[0233]

[0234] From the results of the above examples and comparative examples, it was confirmed that by using the conductive polymer composition according to one embodiment of the present invention, a conductive adhesive film having a relatively low surface resistance and exhibiting antistatic properties, and a conductive adhesive for obtaining such a conductive adhesive film, can be obtained.

[0235] Furthermore, the conductive adhesive film according to one embodiment of the present invention showed no change in appearance and was very good.

[0236] From the above results, it is believed that the excellent antistatic properties and minimal change in appearance of the conductive adhesive film according to one embodiment of the present invention are unique effects based on the conductive polymer composition according to one embodiment of the present invention, and that these effects are due to the combination of the polythiophene (A) and the polyether-based compound (B).

[0237] Example 152 (Preparation and Evaluation of Conductive Release Agent) 0.17 g of LTC310 manufactured by Toray Dow Co., Ltd. as the release agent (F), 4.83 g of 2-butanone as the organic solvent (C), and 0.15 g of the conductive polymer composition prepared in Example 151 above were mixed and stirred for 15 minutes. Subsequently, 0.0033 g of cured platinum catalyst SRX212 manufactured by Toray Dow Co., Ltd. was added, and the mixture was stirred for 15 minutes to prepare a conductive release agent according to one embodiment of the present invention. In this conductive release agent, the conductive polymer composition exhibited high dispersibility. Using the conductive release agent two hours after preparation, a conductive release layer according to one embodiment of the present invention was produced according to the above-mentioned [Method for Measuring the Surface Resistance of a Conductive Release Layer], and the surface resistance was measured. ９ The results are shown in Table 8.

[0238] Examples 153 and 154 (Preparation and Evaluation of Conductive Release Agents) Conductive release agents according to one embodiment of the present invention were prepared by the same procedure as in Example 152, except that 0.17 g of SRX211 or 0.17 g of LTC750A manufactured by Toray Dow Co., Ltd. were used instead of 0.17 g of LTC310 manufactured by Toray Dow Co., Ltd. In both conductive release agents, the conductive polymer composition exhibited high dispersibility. Using each of the obtained conductive release agents, conductive release layers according to one embodiment of the present invention were produced according to the above-mentioned [Method for Measuring Surface Resistance of Conductive Release Layer], and the surface resistance was measured. The formulations and measurement results are shown in Table 8.

[0239] Example 155 (Preparation and Evaluation of Conductive Release Agent) 0.17 g of SRX211 manufactured by Toray Dow Co., Ltd. as the release agent (F), 4.83 g of 2-butanone as the organic solvent (C), and 0.50 g of the conductive polymer composition prepared in Example 151 above were mixed and stirred for 15 minutes. Subsequently, 0.0033 g of cured platinum catalyst SRX212 manufactured by Toray Dow Co., Ltd. was added, and the mixture was stirred for 15 minutes to prepare a conductive release agent according to one embodiment of the present invention. In this conductive release agent, the conductive polymer composition exhibited high dispersibility. Using the conductive release agent 18 hours after preparation, a conductive release layer according to one embodiment of the present invention was produced according to the above [Method for Measuring Surface Resistance of a Conductive Release Layer], and the surface resistance was measured. The result was 10 ８ The results are shown in Table 8.

[0240] Example 157 (Preparation and Evaluation of Conductive Release Agent) 0.17 g of LTC750A manufactured by Toray Dow Co., Ltd. as the release agent (F), 4.83 g of 2-butanone as the organic solvent (C), and 0.15 g of the conductive polymer composition prepared in Example 156 above were mixed and stirred for 15 minutes. Subsequently, 0.0033 g of cured platinum catalyst SRX212 manufactured by Toray Dow Co., Ltd. was added, and the mixture was stirred for 15 minutes to prepare a conductive release agent according to one embodiment of the present invention. In this conductive release agent, the conductive polymer composition exhibited high dispersibility. Using the conductive release agent two hours after preparation, a conductive release layer according to one embodiment of the present invention was produced according to the above-mentioned [Method for Measuring the Surface Resistance of a Conductive Release Layer], and the surface resistance was measured. The result was 10 ９ The results are shown in Table 8.

[0241]

[0242] From the above results, it is believed that the high dispersibility of the conductive material in the conductive release agent according to one embodiment of the present invention is a unique effect of the conductive polymer composition according to one embodiment of the present invention, and that this effect is due to the combination of the polythiophene (A) and the polyether-based compound (B).

[0243] Example 187 (Preparation and Evaluation of Conductive Resin Composition) 2 g of UA-1100H (corresponding to the oligomer (e1) described above) manufactured by Shin-Nakamura Chemical Co., Ltd. as the ultraviolet-curable resin (E), 2 g of 2-hydroxyethyl acrylate (corresponding to the monomer (e2) described above), 0.3 g of 1-hydroxycyclohexyl phenyl ketone (corresponding to the photopolymerization initiator (e3) described above), 5.3 g of 1-methoxy-2-propanol as the organic solvent (C), and 0.4 g of the conductive polymer composition prepared in Example 186 above were mixed and stirred for 15 minutes to prepare a conductive resin composition according to one embodiment of the present invention. In this conductive resin composition, the conductive polymer composition exhibited high dispersibility. Using the conductive resin composition one hour after preparation, a conductive hard coat according to one embodiment of the present invention was produced according to the above [Method for Measuring Surface Resistance of a Conductive Hard Coat], and the surface resistance was measured. １０The results are shown in Table 9.

[0244] Examples 189, 191, and 193 Conductive resin compositions according to one embodiment of the present invention were prepared by the same procedure as in Example 187, except that 0.4 g of the conductive polymer composition of Example 186 was replaced with 0.4 g of the conductive polymer composition of Example 188, 190, or 192. In all of the conductive resin compositions, the conductive polymer composition exhibited high dispersibility. Using each of the resulting conductive resin compositions, conductive hard coats according to one embodiment of the present invention were produced according to the above-described "Method for Measuring Surface Resistance of Conductive Hard Coats," and the surface resistance was measured. The formulations and measurement results for each composition are shown in Table 9.

[0245]

[0246] From the above results, it is believed that the high dispersibility of the conductive material in the conductive resin composition according to one embodiment of the present invention is a unique effect of the conductive polymer composition according to one embodiment of the present invention, and that this effect is due to the combination of the polythiophene (A) and the polyether-based compound (B).

[0247] The conductive polymer composition according to one aspect of the present invention can be used for, for example, a conductive pressure sensitive adhesive, a conductive resin composition, a conductive release agent, an antistatic material, a solid electrolyte for a capacitor, a conductive paint, a conductive primer, a filler dispersant, a battery material, a solar cell, an electromagnetic wave shielding material, a chemical sensor, an actuator, an electrochromic element, an LCD, an organic EL, or a transparent electrode.

Claims

1. A conductive polymer composition comprising: a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether compound (B) represented by the following general formula (16). [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group. [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.] 2. The conductive polymer composition according to claim 1, wherein the polythiophene (A) is a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of structural units represented by the following general formula (3) and structural units represented by the following general formula (4): [In the general formula (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium ion. ２ represents a hydrogen atom, a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 6 carbon atoms, or a fluorine atom; m represents an integer of 1 to 10; and n represents 0 or 1.

3. Said M ＋ is a hydrogen ion, a conjugate acid of an amine compound having a total of 5 to 36 carbon atoms, or a quaternary ammonium ion having a total of 5 to 36 carbon atoms.

4. Said M ＋ is at least one selected from the group consisting of dioctylammonium ion, tridecylammonium ion, hexadecylammonium ion, octadecylammonium ion, oleylammonium ion, di-n-octylammonium ion, bis(2-ethylhexyl)ammonium ion, dimethylstearylammonium ion, trihexylammonium ion, trioctylammonium ion, tris(2-ethylhexyl)ammonium ion, dodecyltrimethylammonium ion, and tetrahexylammonium ion.

5. The conductive polymer composition according to claim 1, wherein n is 1 in the general formula (16).

6. The conductive polymer composition according to claim 1, further comprising an organic solvent (C).

7. The conductive polymer composition according to claim 6, wherein the organic solvent (C) is at least one selected from the group consisting of alcohol-based solvents, glycol ether-based solvents, ether-based solvents, ketone-based solvents, ester-based solvents, amide-based solvents, and aromatic hydrocarbon-based solvents.

8. The conductive polymer composition according to claim 6, wherein the content of the polythiophene (A) is 0.01 to 10 parts by mass per 100 parts by mass of the organic solvent (C).

9. The conductive polymer composition according to claim 6, wherein the content of the polyether compound (B) is 0.01 to 20 parts by mass per 100 parts by mass of the organic solvent (C).

10. A conductive adhesive comprising the conductive polymer composition according to any one of claims 1 to 9 and an adhesive (D).

11. The conductive adhesive according to claim 10, wherein the adhesive (D) is an acrylic adhesive.

12. A method for producing a conductive adhesive film, comprising the steps of applying the conductive adhesive according to claim 10 to a substrate to produce a coating film, and heating the coating film.

13. A conductive adhesive film comprising: a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); a polyether compound (B) represented by the following general formula (16); and an adhesive (D). [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group. [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.] 14. A conductive resin composition comprising the conductive polymer composition according to any one of claims 1 to 9 and an ultraviolet-curable resin (E).

15. A method for producing a conductive hard coat, comprising applying the conductive resin composition according to claim 14 to a substrate and irradiating the substrate with ultraviolet light.

16. A conductive hard coat comprising: a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether compound (B) represented by the following general formula (16). [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group. [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.] 17. A conductive release agent comprising the conductive polymer composition according to any one of claims 1 to 9 and a release agent (F).

18. A method for producing a conductive release layer, comprising applying the conductive release agent according to claim 17 to a substrate and drying it.

19. A conductive release layer comprising: a polythiophene (A) containing two or more structural units of at least one type selected from the group consisting of a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2); and a polyether compound (B) represented by the following general formula (16). [In the general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. In the general formulas (1) and (2), R represents an organic group having a total of 1 to 18 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group. [In the general formula (16), R ５ Each X independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Each X independently represents h butyleneoxy groups (-CH ２ -CH(CH ２ -CH ３ )—O—) and k propyleneoxy groups (—CH ２ -CH(CH ３ )-O-) and j ethyleneoxy groups (-CH ２ -CH ２ represents a divalent polymer group formed by random polymerization or block polymerization in a random order with (—O—). h, k, and j each independently represent an integer of 0 to 20, provided that h+k+j=3 to 50. m represents an integer of 1 to 5. Each n independently represents an integer of 1 to 5.]