Conductive polymer composition and use thereof

Abstract

Regarding resin compositions which are each for a hard coat to be used for antistatic purposes and to which an ionic liquid or the like is added as described in the background art, and a hard coat to be used for antistatic purposes obtained by using such a resin composition, there is room for further improvement from the viewpoint of achieving both antistatic performance and high hardness. A conductive polymer composition according to one embodiment of the present invention is characterized by comprising: a self-doping type conductive polymer (A); and a compound (B) represented by CR5 2=CR6 2 (R5 and R6 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and two of the organic groups may be bonded to each other to form a ring structure).

Description

Conductive polymer composition and its uses

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

[0002] Plastics are easier to mold than metal or glass, but have the problem of being easily scratched on the surface. This problem can be solved by applying a film such as a hard coat to protect the plastic surface. The applications of hard coats are broadly divided into electronics and non-electronics fields. In recent years, with the advancement of the Internet of Things (IoT) and the development of a wide variety of devices, there is a high demand for hard coats in the electronics field. Specific products that are applied with hard coats include various displays.

[0003] Among hard coats, UV-curable hard coats using UV-curable resins can be processed at lower temperatures and in shorter times than conventional coating agents. These features improve productivity and efficiency, and so they are being used in a variety of applications.

[0004] The basic properties of hard coats are hardness and scratch resistance. In addition to these properties, hard coats used in various displays for optical applications must also have the ability to prevent static buildup to prevent dust from adhering electrostatically. The surface resistivity of a hard coat is an indicator of antistatic ability. The lower the surface resistivity of a hard coat, the better its antistatic ability. Generally, the antistatic ability of hard coats for antistatic applications is imparted by the addition of conductive substances, while the basic properties of hardness and scratch resistance are imparted by the resin that is the main component.

[0005] Conventionally, resin compositions for antistatic hard coats containing ionic compounds, conductive polymers, or ionic liquids as conductive substances, and antistatic hard coats using the same have been developed (see Patent Documents 1 to 3).

[0006] Japanese Patent Publication No. 2012-184349 Japanese Patent Publication No. 2013-105178 Japanese Patent Publication No. 2016-216635

[0007] With regard to the resin composition for antistatic hard coating to which an ionic liquid or the like described in the Background Art has been added, and the conductive film such as an antistatic hard coating using the same, there is room for further improvement from the viewpoint of achieving both antistatic performance and high hardness.

[0008] An object of one aspect of the present invention is to provide an excellent conductive film such as a hard coat that has both excellent antistatic properties and high hardness and is not available in the past.

[0009] As a result of extensive research into solving the above problems, the present inventors have found that the invention described below solves the above problems, and have completed the present invention.

[0010] The conductive polymer composition according to one aspect of the present invention comprises a self-doping conductive polymer (A) and a CR ５ ２ =CR ６ ２ (R ５ , R ６ and each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and the two organic groups may be bonded to each other to form a ring structure.

[0011] The conductive hard coat according to one embodiment of the present invention comprises a self-doping conductive polymer (A) and a CR ５ ２ =CR ６ ２ (R ５ , R ６ and each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and two organic groups may be bonded to each other to form a ring structure), a polymerizable oligomer, and a polymerization initiator.

[0012] According to the conductive polymer composition according to one aspect of the present invention, it is possible to provide an excellent conductive film such as a hard coat that has never been available before, which has both excellent antistatic properties and high hardness.

[0013] One 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."

[0014] A variety of hard coats have been developed for antistatic applications, but since there is often a trade-off between the properties required of hard coats, it is generally difficult to create a hard coat that satisfies all of the required properties.

[0015] For example, in a hard coat using an ionic liquid as a conductive material, the amount of the ionic liquid needs to be increased to obtain sufficient antistatic properties. However, as the amount of the ionic liquid increases, the hardness of the hard coat decreases. Therefore, in the case of a hard coat using an ionic liquid, the hardness is sacrificed when antistatic properties are imparted.

[0016] Details will be described later using specific examples, but the conductive polymer composition according to one embodiment of the present invention can provide a hard coat that is imparted with sufficient antistatic properties and exhibits unprecedentedly high hardness, and thus has the remarkable effect of achieving both antistatic properties and scratch resistance at a high level.

[0017] Furthermore, hard coats using ionic liquids as conductive materials have a problem in that their antistatic properties are highly humidity dependent, and when the humidity drops, they no longer exhibit sufficient antistatic properties.

[0018] In contrast, it has been found that the conductive polymer composition according to one embodiment of the present invention has a small humidity dependency of antistatic ability, and has the effect of being able to provide a hard coat that exhibits stable antistatic ability without being affected by humidity changes.

[0019] Furthermore, the conductive polymer composition according to one embodiment of the present invention has the effect of providing a hard coat that exhibits antistatic properties and also has high water repellency and antifouling properties.

[0020] That is, the conductive polymer composition according to one embodiment of the present invention has a remarkable effect in that it can provide a hard coat that exhibits antistatic properties that can simultaneously achieve multiple functions, such as sufficient antistatic properties, high hardness, humidity independence, antifouling properties, and water repellency.

[0021] Furthermore, the conductive polymer composition according to one aspect of the present invention can provide not only an excellent conductive hard coat but also an unprecedentedly excellent conductive adhesive film that combines excellent antistatic properties, excellent adhesiveness, and excellent moisture resistance. Furthermore, the conductive polymer composition can also provide an unprecedentedly excellent conductive release layer that combines excellent antistatic properties, excellent releasability, and excellent moisture resistance.

[0022] The conductive polymer composition according to one aspect of the present invention comprises a self-doping conductive polymer (A) and a CR ５ ２ =CR ６ ２ (R ５ , R ６ and each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and the two organic groups may be bonded to each other to form a ring structure.

[0023] Conductive polymers are broadly classified into externally doped conductive polymers and self-doped conductive polymers. An example of an externally doped conductive polymer is PEDOT / PSS, which is a conductive polymer in which PSS acts as a dopant. A self-doped conductive polymer is a conductive polymer that exhibits conductivity even in the absence of an external dopant such as PSS.

[0024] Examples of the self-doping conductive polymer include polythiophene having an acidic group in the molecule, polypyrrole having an acidic group in the molecule, and polyaniline having an acidic group in the molecule.

[0025] The acidic group is not particularly limited, but examples thereof include a sulfonic acid group, a sulfate group, a phosphinic acid group, a phosphonic acid group, a phosphoric acid group, and a carboxyl group.

[0026] The self-doping conductive polymer (A) according to one aspect of the present invention is preferably a polythiophene (A1) 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 following general formula (1) and a structural unit represented by the following general formula (2), in that it can provide a conductive hard coat having excellent antistatic properties:

[0027] [In the above 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 above general formulas (1) and (2), R represents an organic group having a total of 1 to 14 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.]

[0028] R in general formulas (1) and (2) － represents a state in which the sulfonic acid group or phosphonic acid group contained in R is ionized, and in the general formula (1), M ＋ This represents a state in which a cation represented by the formula (I) is ionic bonded.

[0029] In the above general formula (1), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation.

[0030] The alkali metal ions are preferably, for example, Li ions, Na ions, or K ions.

[0031] The conjugate acid of the above amine compound is a compound in which the amine compound has a hydron (H ＋ The amine compound may be any amine compound that reacts with a sulfonic acid group or a phosphonic acid group to form a conjugate acid, and may be an amine compound having an sp3 hybrid orbital and an N(R １ ) ３ An amine compound represented by the formula (the conjugate acid is [NH(R １ ) ３ ] ＋

[0039] , pyridine compounds having an sp2 hybrid orbital, or imidazole compounds.

[0032] Substituent R １ each independently represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having a substituent and a total of 1 to 18 carbon atoms.

[0033] The alkyl group having 1 to 18 carbon atoms is not particularly limited, and examples thereof include a methyl group, an ethyl group, 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, a cyclohexyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, and an octadecyl group.

[0034] Examples of the substituted alkyl group having 1 to 18 carbon atoms in total include a halogen atom, an alkyl group having 1 to 18 carbon atoms, an amino group, or an alkyl group having 1 to 18 carbon atoms and a hydroxy group, and specific examples include a trifluoromethyl group, a 2-hydroxyethyl group, and the like.

[0035] Among these, the substituent R １ are preferably independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, or a 2-hydroxyethyl group.

[0036] N(R) forming the conjugate acid of the amine compound １ ) ３Examples of the amine compound represented by the formula (I) include ammonia, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, normal-propylamine, isopropylamine, normal-butylamine, tertiary butylamine, dibutylamine, tributylamine, hexylamine, dihexylamine, trihexylamine, octylamine, dioctylamine, trioctylamine, ethanolamine compounds (e.g., aminoethanol, dimethylaminoethanol, methylaminoethanol, diethanolamine, N-methyldiethanolamine, triethanolamine), 3-amino-1,2-propanediol, 3-methylamino-1,2-propanediol, 3-dimethylamino-1,2-propanediol, N-isopropyl-N,N-dimethylamine, and N-ethyl-N,N-dimethylamine.

[0037] N (R １ ) ３ Examples of compounds other than the amine compounds represented by the formula (I) include imidazole compounds (for example, imidazole, N-methylimidazole, or 1,2-dimethylimidazole), pyridine, picoline, or lutidine.

[0038] The total number of carbon atoms in the conjugated acid of the amine compound is not particularly limited, but may be 1 to 30. From the viewpoint of solubility, the total number of carbon atoms is preferably 4 to 30, more preferably 5 to 30, more preferably 5 to 25, more preferably 12 to 24, and more preferably 18 to 24.

[0039] Examples of the quaternary ammonium cation include tetramethylammonium cation, tetraethylammonium cation, tetra-normal-propylammonium cation, tetra-normal-butylammonium cation, and tetra-normal-hexylammonium cation. From the viewpoint of availability, the tetramethylammonium cation and the tetraethylammonium cation are preferred.

[0040] The total number of carbon atoms in the quaternary ammonium cation is not particularly limited, but may be, for example, 4 to 30, preferably 5 to 30, and more preferably 8 to 16.

[0041] In the above general formulas (1) and (2), R represents an organic group having a total of 1 to 14 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0042] The organic group having a total carbon number of 1 to 14 can also be rephrased as a hydrocarbon group having a total carbon number of 1 to 14 which may have a substituent, and is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tetradecyl group, a propyloxymethyl group, and a butyloxymethyl group.

[0043] The self-doping conductive polymer (A) is not particularly limited, but is more preferably a polythiophene (A2) containing at least two or more structural units 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), or a polythiophene (A3) containing at least two or more structural units selected from the group consisting of structural units represented by the following general formula (5) and structural units represented by the following general formula (6), in that it can provide a conductive hard coat with excellent antistatic properties. Note that the polythiophene (A3) is more preferably a polythiophene (A3') containing at least two or more structural units selected from the group consisting of structural units represented by the following general formula (5') and structural units represented by the following formula (6'):

[0044] [In the above general formula (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. ２represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom; m represents an integer of 1 to 6; and n represents 0 or 1.

[0045] [In the above general formula (5), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. ３ R independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom. ４ represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, p represents 0 or 1, q represents an integer of 0 to 6, and r represents 0 or 1.

[0046] [In the above general formula (5'), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation.

[0047] M in the above general formulas (3), (5), and (5′) ＋ The definition and preferred range of M in general formula (1) ＋ The definition and preferred range are the same as those of the above.

[0048] R in the above general formulas (3) and (4) ２ and R in the above general formulas (5) and (6) ３ represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom.

[0049] Examples of the linear or branched alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, 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.

[0050] The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and the like.

[0051] R ２ and R ３ From the viewpoint of film-forming properties, R is preferably a hydrogen atom, a methyl group, an ethyl group, or a fluorine atom. ２ With regard to R, from the viewpoint of film-forming properties, it is more preferable that R is a hydrogen atom or a methyl group, and it is even more preferable that R is a methyl group. ３ In terms of film-forming properties, it is more preferable that the group is a hydrogen atom or a methyl group, and it is most preferable that the group is a hydrogen atom.

[0052] R in the above general formulas (5) and (6) ４ represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.

[0053] Examples of the linear or branched alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, 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.

[0054] R ４ In terms of film-forming properties, the group is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0055] In the above formulas (3) and (4), m represents an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably 2 or 3.

[0056] In the above formulas (3) and (4), n is 0 or 1, preferably 1. In the above formulas (5) and (6), p represents 0 or 1, preferably 0. In the above formulas (5) and (6), q represents an integer of 0 to 6, preferably 0. In the above formulas (5) and (6), r represents 0 or 1, preferably 0.

[0057] The structural units represented by the general formulas (2), (4), (6), and (6') represent the self-doping state of the structural units represented by the general formulas (1), (3), (5), and (5'), respectively, and this doping state is achieved by the sulfonic acid group or phosphonic acid group in the structural units represented by the general formulas (1), (3), (5), and (5') acting as a p-type dopant. Polymers that exhibit conductivity without the addition of an external dopant in this way are called self-doping polymers.

[0058] The polythiophene (A1) can be produced by polymerizing a thiophene monomer represented by the following general formula (7) in water or an alcohol solvent in the presence of an oxidizing agent, followed by acid treatment as needed.

[0059] [M in the above general formula (7)] ＋ represents a hydrogen ion or a metal ion.

[0060] The polythiophene (A2) can be produced by polymerizing a thiophene monomer represented by the following general formula (8) in water or an alcohol solvent in the presence of an oxidizing agent, followed by acid treatment as needed.

[0061] [In the above general formula (8), M ＋ represents a hydrogen ion or a metal ion. ２ Regarding R in the above general formula (1), ２ m represents an integer of 1 to 6, and n represents 0 or 1.

[0062] The polythiophene (A3) can be produced by polymerizing a thiophene monomer represented by the following general formula (9) in water or an alcohol solvent in the presence of an oxidizing agent, followed by acid treatment as needed.

[0063] [In the above general formula (9), M ＋ represents a hydrogen ion or a metal ion. ３ R independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom.４ represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, p represents 0 or 1, q represents an integer of 0 to 6, and r represents 0 or 1.

[0064] The polythiophene (A3') of this embodiment can be produced by polymerizing a thiophene monomer represented by the following general formula (9') in water or an alcohol solvent in the presence of an oxidizing agent, and then optionally treating with an acid.

[0065] [In the above general formula (9'), M ＋ represents a hydrogen ion or a metal ion.

[0066] M in the above general formulae (7), (8), (9), and (9′) ＋ The metal ion represented by the formula (I) is not particularly limited, but examples thereof include transition metal ions, noble metal ions, non-ferrous metal ions, alkali metal ions (e.g., Li ions, Na ions, or K ions), and alkaline earth metal ions.

[0067] When the polymer obtained after polymerization of the thiophene monomers represented by the general formulas (7), (8), (9), and (9′) is a salt of a metal ion, the obtained metal salt polymer can be treated with an acid to obtain M ＋ can be converted into hydrogen ions.

[0068] The thiophene monomer represented by the general formula (8) is not particularly limited, but specific examples thereof include 6-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)hexane-1-sulfonic acid, sodium 6-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)hexane-1-sulfonate, lithium 6-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)hexane-1-sulfonate, and 6-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)hexane-1-sulfonate. ) hexane-1-sulfonic acid potassium, 8-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)octane-1-sulfonic acid, 8-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)octane-1-sulfonic acid sodium, 8-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)octane-1-sulfonic acid potassium, 3-[(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy]-1-propanesulfonic acid sodium, 3-[(2 ,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-propanesulfonate potassium, 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonate sodium, 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-ethyl-1-propanesulfonate sodium, 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-propyl-1- Sodium propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-butyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-pentyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-hexyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-hexyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-isopropyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-isobutyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-isopentyl-1-propanesulfonate, sodium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]- Sodium 1-fluoro-1-propanesulfonate, potassium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonate, 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonic acid, ammonium 3-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonate, Triethylammonium hydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-propanesulfonate, sodium 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-butanesulfonate, potassium 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-butanesulfonate, 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]- Examples include sodium 1-methyl-1-butanesulfonate, potassium 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-methyl-1-butanesulfonate, sodium 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-fluoro-1-butanesulfonate, and potassium 4-[(2,3-dihydrothieno[3,4-b]-[1,4]dioxin-2-yl)methoxy]-1-fluoro-1-butanesulfonate.

[0069] In this embodiment, the conductivity of the self-doped conductive polymer (A) and the polythiophenes (A1), (A2), (A3) and (A3′) is not particularly limited, but it is preferable that the conductivity (electrical conductivity) in the film state is 10 S / cm or more, in order to provide a conductive hard coat having excellent antistatic properties.

[0070] The self-doping conductive polymer (A) and the polythiophenes (A1), (A2), (A3) and (A3') in this embodiment may be synthesized based on publicly known information.

[0071] The contents of the self-doped conductive polymer (A) and the polythiophenes (A1), (A2), (A3) and (A3') in the conductive polymer composition according to an embodiment of the present invention are not particularly limited, but are preferably 0.01 to 30% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, relative to 100% by mass of the total amount of the conductive polymer composition according to an embodiment of the present invention, in order to provide a conductive hard coat having excellent antistatic properties.

[0072] The above CR ５ ２ =CR ６ ２ (R ５ , R ６ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and two organic groups may be bonded to each other to form a ring structure), the compound (B) represented by ５ ２ =CR ６ - represents a compound having a group represented by 1 to 6 CR in the molecule, and can provide a conductive hard coat having excellent hardness. ５ ２ =CR ６ Preferably, the compound has one or two CR groups in the molecule. ５ ２ =CR ６ It is more preferable that the compound has a group represented by -.

[0073] R in compound (B) ５ , R ６ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group.

[0074] The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0075] The organic group is not particularly limited, but examples thereof include a methyl group, an ethyl group, a propyl group, an acetyl group, a propionyl group, a methoxy group, an ethoxy group, a pyrrolidone group, a carbazolyl group, a phenyl group, a formyl group, an acetyl group, a propanoyl group, a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an aminocarbonyl group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group, an allyl group, and a 2-chloroallyl group.

[0076] The compound (B) is not particularly limited, but examples thereof include styrene monomer, divinylbenzene monomer, vinyl acetate monomer, acrylic acid, methacrylic acid, acrylate monomer, methacrylate monomer, acrylamide monomer, methacrylamide monomer, acrylic silane monomer, and methacrylic silane monomer. More specifically, examples thereof include acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, isopropyl acrylate, tertiary butyl acrylate, isobutyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, tetradecyl acrylate, hexadecyl acrylate, stearyl acrylate, trifluoroethyl acrylate, octafluoropentyl acrylate, 2-cyanoethyl acrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 2-methoxyethyl acrylate, allyl acrylate, diethylene glycol monoethyl ether acrylate, mono(2-acryloyloxyethyl)succinate, 2-(dimethylamino)ethyl acrylate, phenoxyethyl acrylate, phenyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, 1-(acryloyloxy)-3-(methacryloyloxy)-2-propanol, 2-hydroxy-3-phenoxypropyl acrylate, 2,3-dibromopropyl acrylate, 3-(trimethoxysilyl)propyl acrylate, trimethylsilyl acrylate, pentafluorophenyl acrylate, 2,4,6-tributylphenyl acrylate, N-succinimidyl acrylate, dicyclopentanyl acrylate, isobornyl acrylate, pentabromobenzyl acrylate, methacrylic acid, 2-(trifluoro)methacrylic acid, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, isopropyl methacrylate, tertiary butyl methacrylate, isobutyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, Stearyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, pentafluoropropyl methacrylate, 2,2,3,4,4,4-hexafluorobutyl methacrylate, 1H,1H,2H,2H-tridecafluoro-n-octyl methacrylate, vinyl methacrylate, allyl methacrylate, 2-hydroxyethyl methacrylate, 3-hydroxybutyl methacrylate, 2-methoxyethyl methacrylate, 2-ethoxyethyl methacrylate, ethylene glycol monoacetoacetate mono Methacrylate, diethylene glycol monomethyl ether methacrylate, cyclohexyl methacrylate, benzyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-(diethylamino)ethyl methacrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate, furfuryl methacrylate, mevalonate lactone methacrylate, 3-chloro-2-hydroxypropyl methacrylate, 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, 2-methacryloyloxyethyl Phosphorylcholine, 2-(trimethylsilyloxy)ethyl methacrylate, 3-(trimethoxysilyl)propyl methacrylate, 3-(triethoxysilyl)propyl methacrylate, 3-[tris(trimethylsilyloxy)silyl]propyl methacrylate, 3-[diethoxy(methyl)silyl]propyl methacrylate, N-succinimidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 4-methacryloyloxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical, dicyclopentanyl methacrylate, isobornyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2-ethyl-2-adamantyl methacrylate, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, pentafluorobenzyl methacrylate, 9-anthrylmethyl methacrylate, acrylamide, N-isopropylacrylamide, N-tertiarybutylacrylamide, N-dodecylacrylamide, N- (Butoxymethyl)acrylamide, N-(hydroxymethyl)acrylamide, N-(2-hydroxyethyl)acrylamide, N-acrylamidohexanoic acid, 2-acrylamido-2-methylpropanesulfonic acid, N,N-dimethylacrylamide, N,N-diethylacrylamide, N-[3-(dimethylamino)propyl]acrylamide, (3-acrylamidopropyl)trimethylammonium chloride, 4-acryloylmorpholine, 3-acryloyl-2-oxazolidinone, N-phenylacrylamide, 1,3,5-triacryloyl hexahydro-1,3,5-triazine, N,N'-methylenebisacrylamide, N,N'-ethylenebisacrylamide, methacrylamide, N-methylmethacrylamide, N-isopropylacrylamide, N-tert-butylmethacrylamide, N-(methoxymethyl)methacrylamide, N-(3-dimethylaminopropyl)methacrylamide, N,N-dimethylmethacrylamide, N-phenylmethacrylamide, N-(4-hydroxyphenyl)methacrylamide, N,N'-methylenebismethacrylamide, 3-methacrylamide Phenylboronic acid, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, 1,10-decanediol diacrylate, neopentyl glycol diacrylate, 1,6-bis(acryloyloxy)-2,2,3,3,4,4,5,5-octafluorohexane, tetraethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, ethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, 1,6-Hexanediol dimethacrylate, diethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, glycerol dimethacrylate, 4,4'-isopropylidenediphenol dimethacrylate, 4,4'-thiodibenzenedithiol methacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tris(2-acryloyloxyethyl)isocyanurate Examples of the compound (B) include glycerol trimethacrylate, 2-phenoxyethyl acrylate, dicyclohexyl acrylate, γ-butyrolactone acrylate, γ-butyrolactone methacrylate, 5-oxotetrahydrofuran-3-yl methacrylate, glycol dimethacrylate, diethylene glycol diacrylate, ethylene glycol monomethyl ether acrylate, ethylene glycol monoacrylate, ethylene glycol diacrylate, ethylene glycol monomethacrylate, 1,3-propanediol diacrylate, and 1,3-propanediol dimethacrylate. These compounds (B) may be used alone or in combination of two or more.

[0077] The molecular weight of the compound (B) is not particularly limited, but is preferably 60 to 3,000, more preferably 60 to 1,500, even more preferably 60 to 700, and even more preferably 60 to 500, in order to provide a conductive hard coat having excellent hardness.

[0078] The compound (B) is preferably an acrylic acid compound, a methacrylic acid compound, a maleimide compound, an aromatic vinyl compound, or a vinyl acetate monomer, in terms of being able to provide a conductive hard coat having excellent hardness, and more preferably an acrylic acid compound having 3 to 13 carbon atoms in total, a methacrylic acid compound having 4 to 14 carbon atoms in total, a maleimide compound having 4 to 13 carbon atoms in total, an aromatic vinyl compound having 8 to 14 carbon atoms in total, or a vinyl acetate monomer, and more preferably an acrylate compound having 3 to 13 carbon atoms in total, a methacrylate compound having 4 to 14 carbon atoms in total, an acrylamide compound having 3 to 13 carbon atoms in total, a methacrylamide compound having 4 to 14 carbon atoms in total, a maleimide compound having 4 to 13 carbon atoms in total, an aromatic vinyl compound having 8 to 14 carbon atoms in total, or a vinyl acetate monomer, and more preferably an acrylic acid, methacrylic acid, methyl More preferably, the monomer is selected from the group consisting of methyl acrylate, methyl methacrylate, butyl acrylate, dodecyl acrylate, stearyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-methoxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, diethylene glycol monoethyl ether acrylate, 2-(dimethylamino)ethyl acrylate, 2-phenoxyethyl acrylate, dicyclohexyl acrylate, isobornyl acrylate, 4-acryloylmorpholine, mono(2-acryloyloxyethyl)succinate, acrylamide, methacrylamide, vinyl acetate monomer, styrene monomer, and divinylbenzene monomer.

[0079] The content of the compound (B) in the conductive polymer composition according to one embodiment of the present invention is not limited, but is preferably 70 to 99.99 mass %, and more preferably 90 to 99.9 mass %, relative to 100 mass % of the entire conductive polymer composition.

[0080] The conductive polymer composition according to one aspect of the present invention may further contain a polymerizable oligomer.

[0081] The polymerizable oligomer refers to a polymer composed of a plurality of repeating units to which at least one polymerizable group, exemplified by an acrylic group or a methacrylic group (hereinafter both of which will be referred to as "(meth)acrylic group"), is bonded. For example, it can include a polymer selected from the group consisting of polyoxyethylene, polyurethane, polyester, polyacrylic acid, polymethacrylic acid, poly(oxyperfluoroalkylene), etc. to which at least one polymerizable group, exemplified by (meth)acrylic, etc., is bonded.

[0082] The number of polymerizable groups represented by (meth)acrylic groups or the like contained in the polymerizable oligomer is not limited, and may be one, two, three, four, five, or more.

[0083] The polymerizable oligomer is not particularly limited, but examples thereof include urethane (meth)acrylate oligomers, epoxy (meth)acrylate oligomers, polyoxyethylene (meth)acrylate oligomers, polyoxypropylene (meth)acrylate oligomers, polyester (meth)acrylate oligomers, poly(meth)acrylic acid (meth)acrylate oligomers, and poly(oxyperfluoroalkylene) (meth)acrylate oligomers, etc. These polymerizable oligomers may be used alone or in combination of two or more.

[0084] The polymerizable oligomer is preferably at least one selected from the group consisting of urethane (meth)acrylate oligomers and epoxy (meth)acrylate oligomers, since it can provide a conductive hard coat having excellent hardness.

[0085] In addition, the polymerizable oligomer preferably contains a (meth)acrylate oligomer having 15 or less functionalities (i.e., the number of (meth)acrylic groups in the oligomer is 15 or less), and more preferably contains a (meth)acrylate oligomer having 10 or less functionalities, in order to provide a conductive hard coat having excellent hardness.

[0086] Examples of the polymerizable oligomer include UA-1100H (manufactured by Shin-Nakamura Chemical Co., Ltd.), UN-904 (manufactured by Negami Chemical Industrial Co., Ltd.), RUA-071 (manufactured by Asia Industries Co., Ltd.), RUA-076MG (manufactured by Asia Industries Co., Ltd.), EBECRYL 600 (manufactured by Daicel-Allnex Corporation), X-40-2669 (manufactured by Shin-Etsu Silicones Co., Ltd.), and KR-470 (manufactured by Shin-Etsu Silicones Co., Ltd.). These may be used alone or in combination of two or more.

[0087] The content of the polymerizable oligomer is not limited, but is preferably 5 to 80 mass %, more preferably 5 to 60 mass %, even more preferably 5 to 40 mass %, and still more preferably 5 to 30 mass %, relative to 100 mass % of the entire conductive polymer composition according to one embodiment of the present invention, in terms of being able to provide a conductive hard coat having excellent hardness.

[0088] The conductive polymer composition according to one aspect of the present invention may contain a polymerization initiator. Any polymerization initiator used in the relevant field may be used without 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.

[0089] The content of the polymerization initiator is not limited, but is preferably 0.1 to 10 mass %, more preferably 0.2 to 8 mass %, and even more preferably 0.5 to 5 mass %, relative to 100 mass % of the entire conductive polymer composition according to one embodiment of the present invention, in terms of being able to provide a conductive hard coat having excellent hardness.

[0090] The content of the polymerization initiator is not limited, but is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 5 to 20 parts by mass, relative to 100 parts by mass of the total weight of the compound (B) and the polymerizable oligomer, in terms of being able to provide a conductive hard coat having excellent hardness.

[0091] The conductive polymer composition according to one aspect of the present invention may further contain a dispersant (C).

[0092] The dispersant (C) is not particularly limited, but any dispersant known in the art as a dispersant for conductive polymer compositions can be used without limitation as long as it can dissolve or disperse each of the components contained together in the conductive polymer composition according to one embodiment of the present invention. The dispersant (C) may be any commonly known, commercially available dispersant, and is not particularly limited, but examples thereof include polyether-based dispersants, polyester-based dispersants, polyamine-based dispersants, polyethyleneimine-based dispersants, silicone-based dispersants, polyacrylic-based dispersants, polyurethane-based dispersants, polycaprolactone-based dispersants, and other commercially available dispersants.

[0093] Examples of polyester dispersants that can be used include Disparlon KS873N, Disparlon DA703-50, and Disparlon DA7400 (all manufactured by Kusumoto Chemical Co., Ltd.).

[0094] Examples of polyacrylic dispersants include Disperbyk-2000, Disperbyk-2001, Disperbyk-2008, Disperbyk-2009, Disperbyk-2010, Disperbyk-2020, Disperbyk-2020N, ​​Disperbyk-2022, Disperbyk-2025, Disperbyk-2050, Disperbyk-2070, Disperbyk-2095, Disperbyk-2150, Disperbyk-2151, Disperbyk-2155, Disperbyk k-2163, Disperbyk-2164, BYKJET-9130, BYKJET-9131, BYKJET-9132, BYKJET-9133, BYKJET-9151, BYK-9076, BYK-9077 (all manufactured by BYK-Chemie), EfkaPX4310, EfkaPX4320, EfkaPX4330, EfkaPA4401, EfkaPA4402, EfkaPA4403, EfkaPA4570, EfkaPA7411, EfkaPA7477, EfkaPX4700, EfkaPX4701 (all manufactured by BASF), TREPLUS Examples of suitable solvents include TREPLUS D-1200, TREPLUS D-1410, TREPLUS D-1420, and TREPLUS MD-1000 (all manufactured by Otsuka Chemical Co., Ltd.), FLOWRENE DOPA-15BHFS, FLOWRENE DOPA-17HF, FLOWRENE DOPA-22, FLOWRENE G-700, FLOWRENE G-900, FLOWRENE NC-500, and FLOWRENE GW-1500 (all manufactured by Kyoeisha Chemical Co., Ltd.).

[0095] As the polyamine-based dispersant, for example, Disparlon 1860 (manufactured by Kusumoto Chemical Co., Ltd.) is used.

[0096] Examples of polycaprolactone-based dispersants include Ajisper PB821, Ajisper PB822, Ajisper PB824, and Ajisper PB881 (all manufactured by Ajinomoto Fine-Techno Co., Ltd.), Hinoact KF-1000, Hinoact KF-1500, Hinoact KF-1700, Hinoact T-6000, Hinoact T-7000, Hinoact T-8000, Hinoact T-8000E, and Hinoact T-9050 (all manufactured by Kawaken Fine Chemicals Co., Ltd.), Solsperse 20000, Solsperse 24000, and Solsperse rse32000, Solsperse32500, Solsperse32550, Solsperse32600, Solspe rse33000, Solsperse33500, Solsperse34000, Solsperse35200, Solsper se36000, Solsperse37500, Solsperse39000, Solsperse71000, Solspers e76400, Solsperse76500, Solsperse86000, Solsperse88000, Solsperse Examples of suitable dispersants include TEGO Disperse J180, Solsperse J200 (all manufactured by Lubrizol Corporation), TEGO Disperse 652, TEGO Disperse 655, TEGO Disperse 685, TEGO Disperse 688, and TEGO Disperse 690 (all manufactured by Evonik Japan).

[0097] Other commercially available dispersants include, for example, Esreem AD-3172M, Esreem AD-374M, Esreem AD-508E, Esreem AD-221P, Esreem AD-221J, Esreem DP-2, Esreem DJ-2, Marialim AKM-0531, Marialim AFB-1521, Marialim AAB-0851, Marialim SC-0505K, Marialim SC-1015F, and Marialim SC-0708A (all manufactured by NOF Corporation).

[0098] As for the dispersant (C), in that they can provide a conductive hard coat having excellent hardness, Hinoact KF-1000, Hinoact T-6000, Hinoact T-8000, S-Leam AD-374M, S-Leam AD-508E, S-Leam AD-3172M, Ajisper PB821, Ajisper PB824, Ajisper PB881, BYK-9076, BYK-9077, etc. are preferred. The dispersants (C) specifically exemplified here can be used alone or in combination of two or more.

[0099] The content of the dispersant (C) is not limited, but is preferably 0.1 to 25 mass %, more preferably 0.5 to 20 mass %, and even more preferably 1 to 10 mass %, relative to 100 mass % of the entire conductive polymer composition according to an aspect of the present invention.

[0100] The conductive polymer composition according to one embodiment of the present invention may contain components other than those described above. Examples of such components other than those described above include, but are not limited to, a water-repellent and antifouling agent (an additive that imparts water repellency and oil repellency), an ultraviolet absorber, an antioxidant, a colorant, an inorganic filler, an antifoaming agent, a thickener, a suspending agent, an antifogging agent, an antibacterial agent, a leveling agent, a solvent (excluding the above-described compound (B)), or a surface modifier. Commercially available products may be used for all of these components.

[0101] Examples of inorganic fillers include single-walled carbon nanotubes, multi-walled carbon nanotubes, silver nanowires, carbon black, silica, alumina, boehmite, antimony oxide, chromium oxide, nickel oxide, copper oxide, tin oxide, titanium oxide, zirconium oxide, indium oxide, and zinc oxide.

[0102] The water-repellent and stain-proofing agent is not particularly limited, but examples thereof include fluorine compounds and silicone compounds.

[0103] Examples of the fluorine compound include perfluoropolyether, X-71-1203E (Shin-Etsu Chemical Co., Ltd.), and KY-1203 (Shin-Etsu Chemical Co., Ltd.).

[0104] Examples of the silicone compound include MEK-ST-ZL (Nissan Chemical), KY-1216 (Shin-Etsu Chemical Co., Ltd.), Megafac RS-851 (DIC), Opstar TU-2225 (Arakawa Chemical Industries, Ltd.), KP-112 (Shin-Etsu Silicones), KP-341 (Shin-Etsu Silicones), and KP-423 (Shin-Etsu Silicones).

[0105] The content of the water-repellent and stain-proofing agent is not limited, but is preferably 0.1 to 5 mass %, and more preferably 0.1 to 2 mass %, relative to 100 mass % of the entire conductive polymer composition according to an embodiment of the present invention.

[0106] The solvent (excluding the compound (B)) is not particularly limited, and any solvent known in the art as a solvent for conductive polymer compositions can be used without limitation as long as it can dissolve or disperse each of the components contained in the conductive polymer composition according to one embodiment of the present invention. Examples of the solvent include alcohol-based solvents, glycol ether-based solvents, ketone-based solvents, ester-based solvents, amide-based solvents, carbonate-based solvents, and aromatic hydrocarbon-based solvents. More specific examples include ethanol, isopropanol, trifluoroethanol, 1-methoxy-2-propanol, ethylene glycol n-butyl ether, methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, diethyl ketone, dipropyl ketone, cyclohexanone, methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, γ-butyrolactone, N-methylformamide, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, ethylene carbonate, propylene carbonate, toluene, and xylene. The solvents specifically exemplified here can be used either alone or in combination of two or more.

[0107] The content of the solvent is not limited, but is preferably 1 to 80 mass %, more preferably 5 to 70 mass %, and even more preferably 10 to 60 mass %, relative to 100 mass % of the entire conductive polymer composition according to an aspect of the present invention.

[0108] The conductive polymer composition according to one aspect of the present invention is not particularly limited, and can be used, for example, as a composition for producing a conductive hard coat, and can also be used as a composition for producing a conductive adhesive film, a conductive release layer, or a conductive cured product, and the conductive polymer composition can be used to produce a conductive hard coat, a conductive adhesive film, a conductive release layer, or a conductive cured product.

[0109] A composition for producing a conductive hard coat according to one embodiment of the present invention is characterized by containing the above-mentioned conductive polymer composition, and preferably further contains a polymerizable oligomer and a polymerization initiator, and more preferably further contains a polymerizable monomer.

[0110] The polymerizable monomer in the composition for producing a conductive hard coat is not particularly limited, but may be, for example, the above-mentioned compound (B). The preferred range of the polymerizable monomer is the same as the preferred range of the above-mentioned compound (B).

[0111] The polymerizable oligomer and the polymerization initiator in the composition for producing the conductive hard coat are as described above.

[0112] The contents of the conductive polymer composition, polymerizable oligomer, polymerization initiator, and polymerizable monomer in the composition for producing a conductive hard coat can be adjusted as desired by those skilled in the art depending on the intended use and physical properties.

[0113] The content of the polymerizable monomer in the composition for producing a conductive hard coat is not limited, but is preferably 5 to 80 mass %, more preferably 5 to 70 mass %, even more preferably 5 to 60 mass %, and still more preferably 5 to 50 mass %, based on 100 mass % of the entire composition for producing a conductive hard coat according to one embodiment of the present invention, in terms of being able to provide a conductive hard coat having excellent hardness.

[0114] By curing the composition for producing the conductive hard coat, a conductive cured product, a conductive hard coat (hard coat film or hard coat film), or a laminate having the conductive hard coat (hard coat film or hard coat film) can be produced, which is characterized by containing the self-doping conductive polymer (A).

[0115] A method for producing a conductive hard coat, a conductive cured product, or a laminate having a conductive hard coat according to one embodiment of the present invention is characterized by comprising the steps of applying the composition for producing a conductive hard coat to a substrate to produce a coating film, and irradiating the coating film with ultraviolet light. Note that, in order to improve the physical properties such as hardness of the conductive cured product, the conductive hard coat, or the laminate having a conductive hard coat, it is preferable that the applied composition for producing a conductive hard coat be dried before the ultraviolet light irradiation.

[0116] The substrate is not particularly limited, but examples thereof include glass, a resin film, a resin plate, and a resist substrate.

[0117] The resin film is not particularly limited, but examples thereof include triacetyl cellulose (TAC) film, polyethylene terephthalate (PET) film, diacetylene cellulose film, acetate butyrate cellulose film, polyethersulfone film, polyacrylic resin film, polyurethane resin film, polyester film, polycarbonate film, polysulfone film, polyether film, polymethylpentene film, polyether ketone film, (meth)acrylonitrile film, and cycloolefin polymer (COP) film.

[0118] Examples of resin plates include acrylic plates, triacetyl cellulose (TAC) plates, polyethylene terephthalate (PET) plates, diacetylene cellulose plates, acetate butyrate cellulose plates, polyethersulfone plates, polyurethane plates, polyester plates, polycarbonate plates, polysulfone plates, polyether plates, polymethylpentene plates, polyether ketone plates, and (meth)acrylonitrile plates.

[0119] All of these substrates have excellent transparency and are suitable for use in the display devices described below. The thickness of the substrate can be selected appropriately depending on the application, but generally, a thickness of about 25 to 1000 μm is used.

[0120] The coating method is not particularly limited, but examples thereof include screen printing, casting, dipping, bar coating, roll coating, gravure coating, flexographic printing, spray coating, air knife coating, curtain coating, spin coating, wire bar coating, extrusion coating, and inkjet printing.

[0121] The coating film obtained by coating may be dried. When drying the coating film, the drying temperature is not particularly limited, 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 room temperature to 200°C, in order to obtain a conductive hard coat in a uniformly dried state.

[0122] When drying the coating film, the drying 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 such as nitrogen or argon is preferred.

[0123] The amount of ultraviolet light irradiation in the above ultraviolet light irradiation is not particularly limited, but is preferably 100 to 21,000 mJ / cm ２ is preferably about 300 to 2100 mJ / cm ２ is.

[0124] The irradiation atmosphere for ultraviolet irradiation is not particularly limited, but may be any of air, inert gas, vacuum, and reduced pressure.

[0125] By carrying out the above-described method for producing a conductive hard coat, a conductive hard coat film can be obtained.

[0126] The thickness of the conductive hard coat (after drying and UV irradiation) is not particularly limited, but is preferably in the range of 1 to 100 μm, more preferably 1 to 10 μm.

[0127] The thickness of the conductive hard coat film (hard coat layer) is not particularly limited, but is preferably 0.01 to 20 μm after application and drying.

[0128] The conductive hard coat produced from the composition for producing a conductive hard coat according to one embodiment of the present invention has high hardness. For example, a conductive hard coat formed to a film thickness of 3 μm using the composition for producing a conductive hard coat according to one embodiment of the present invention preferably has a pencil hardness of H or more, more preferably 2H or more, as measured in accordance with JIS K-5600.

[0129] The above-mentioned conductive cured product, conductive hard coat, or laminate having a conductive hard coat can be used together with a light source and applied to a display device. In this case, the substrate on which the conductive hard coat film is formed is preferably a light-transmitting substrate. As the light-transmitting substrate, the substrates described above for forming the conductive hard coat film can be used. Furthermore, the light source is preferably disposed on the back surface of the substrate, i.e., the surface of the substrate opposite to the surface on which the conductive hard coat layer is formed, and is preferably one that irradiates light toward the substrate from there.

[0130] The light source that can be combined with the conductive cured product, the conductive hard coat, or the laminate having a conductive hard coat is not particularly limited as long as it can emit light, and examples thereof include light-emitting diodes, cold cathode tubes, hot cathode tubes, and EL elements, but a liquid crystal module, a backlight unit, or the like may also be used.

[0131] The liquid crystal module refers to a configuration including the above-mentioned light source and further comprising a polarizer / liquid crystal cell / polarizer arranged thereon in this order. The liquid crystal cell is not particularly limited as long as it is one generally used in liquid crystal display devices. Examples include a TN-type liquid crystal cell, an STN-type liquid crystal cell, an HAN-type liquid crystal cell, an IPS-type liquid crystal cell, a VA-type liquid crystal cell, an MVA-type liquid crystal cell, and an OCB-type liquid crystal cell. Such a display device may further include a retardation plate, a brightness enhancement film, a light guide plate, a light diffusion plate, a light diffusion sheet, a light collecting sheet, or a reflector.

[0132] Examples of display devices equipped with the present laminate include flat panel displays such as liquid crystal displays (liquid crystal displays), LEDs (light-emitting diode displays), ELDs (electroluminescent displays), VFDs (fluorescent displays), and PDPs (plasma display panels). Furthermore, the composition for producing a conductive hard coat according to one embodiment of the present invention, which is used to produce a display device, has weather resistance in addition to anti-blocking properties, making it possible to use these display devices outdoors. For example, it can be installed outdoors or semi-outdoors as a panel display for displaying information such as advertisements.

[0133] Furthermore, examples of applications of display devices including the present laminate include touch panels, which have a mechanism for operating equipment by pressing the display on the screen, and are useful in, for example, bank ATMs, vending machines, personal digital assistants (PDAs), copiers, facsimiles, game machines, guidance display devices installed in facilities such as museums and department stores, car navigation systems, multimedia stations (multifunctional terminals installed in convenience stores), mobile phones, and monitoring devices for railway vehicles.

[0134] A composition for producing a conductive adhesive film according to one embodiment of the present invention is characterized by containing the above-mentioned conductive polymer composition, and preferably further contains a polymerization initiator, and more preferably further contains an adhesive that is commonly used in producing a conductive adhesive film.

[0135] The polymerization initiator in the composition for producing a conductive adhesive film is as described above.

[0136] A method for producing a conductive adhesive film according to one embodiment of the present invention is characterized by comprising the steps of applying the above-mentioned composition for producing a conductive adhesive film to a substrate to produce a coating film, and heating the coating film.

[0137] The substrate is the same as the substrate in the method for producing the conductive hard coat.

[0138] The coating film obtained by coating may be dried.

[0139] The temperature for heating the coating film is not particularly limited, but is preferably in the range of 40 to 250°C, more preferably in the range of 50 to 200°C, and even more preferably in the range of 60 to 150°C, in order to obtain a conductive adhesive film with excellent adhesiveness.

[0140] The atmosphere in which the coating film is heated is not particularly limited, but may be any of air, inert gas, vacuum, and reduced pressure.

[0141] By carrying out the above-described method for producing a conductive adhesive film, a conductive adhesive film can be obtained.

[0142] A composition for producing a conductive release layer according to one embodiment of the present invention is characterized by containing the above-mentioned conductive polymer composition, and preferably further contains a release agent that is commonly used when producing a conductive release layer.

[0143] The release agent is not particularly limited, but examples thereof include wax-based release agents, silicone-based release agents, and fluorine-based release agents.

[0144] 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.

[0145] 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.

[0146] The fluorine-based release agent is not particularly limited, but examples thereof include fluorine oil and polytetrafluoroethylene.

[0147] The content of the release agent in the composition for manufacturing a conductive release layer 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 composition for manufacturing a conductive release layer being 100% by mass.

[0148] 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 layer production composition 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 self-doping conductive polymer (A), the above-mentioned compound (B), and a release agent.

[0149] A method for producing a conductive release layer according to one embodiment of the present invention is characterized by comprising a step of applying the above-mentioned composition for producing a conductive release layer to a substrate to produce a coating film, and a step of drying the coating film.

[0150] The substrate is the same as the substrate in the method for producing the conductive hard coat.

[0151] In the step of drying the coating film, the atmosphere is not particularly limited, and may be any of air, an inert gas, a vacuum, or a reduced pressure.

[0152] The step of drying the coating film may involve heating. The heating temperature is not particularly limited, but is preferably in the range of 40 to 250°C, more preferably in the range of 50 to 200°C, and even more preferably in the range of 60 to 150°C, in order to obtain a conductive release layer with excellent releasability.

[0153] By carrying out the above-described method for producing a conductive release layer, a conductive release layer can be obtained.

[0154] 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.

[0155] One aspect of the present invention may include the following [1] to

[19] . [1] A self-doping conductive polymer (A) and a CR ５ ２ =CR ６ ２ (R ５ , R ６and each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and the two organic groups may be bonded to each other to form a ring structure.

[0156] [2] The conductive polymer composition according to [1], wherein the self-doping conductive polymer (A) is a polythiophene (A1) 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 following general formula (1) and a structural unit represented by the following general formula (2):

[0157] [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 14 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.

[0158] [3] The conductive polymer composition according to [1], wherein the self-doping conductive polymer (A) is a polythiophene (A2) 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 following general formula (3) and a structural unit represented by the following general formula (4):

[0159] [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 cation. ２ represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom; m represents an integer of 1 to 6; and n represents 0 or 1.

[0160] [4] The conductive polymer composition according to [3], wherein in the general formulae (3) and (4), m is 2 or 3.

[0161] [5] In the general formulas (3) and (4), the R ２ is a methyl group.

[0162] [6] In the general formula (3), the M ＋ is a conjugated acid of an amine compound having a total carbon number of 4 to 30, or a quaternary ammonium cation having a total carbon number of 4 to 30.

[0163] [7] The conductive polymer composition according to any one of [1] to [6], wherein the compound (B) has a molecular weight of 60 to 700.

[0164] [8] The conductive polymer composition according to any one of [1] to [7], wherein the compound (B) is an acrylic acid compound, a methacrylic acid compound, a maleimide compound, an aromatic vinyl compound, or a vinyl acetate monomer.

[0165] [9] The conductive polymer composition according to any one of [1] to [7], wherein the compound (B) is an acrylic acid compound having a total carbon number of 3 to 13, a methacrylic acid compound having a total carbon number of 4 to 14, a maleimide compound having a total carbon number of 4 to 13, an aromatic vinyl compound having a total carbon number of 8 to 14, or a vinyl acetate monomer.

[0166]

[10] The conductive polymer composition according to any one of [1] to [7], wherein the compound (B) is an acrylate compound having a total carbon number of 3 to 13, a methacrylate compound having a total carbon number of 4 to 14, an acrylamide compound having a total carbon number of 3 to 13, or a methacrylamide compound having a total carbon number of 4 to 14.

[0167]

[11] The conductive polymer composition according to any one of [1] to

[10] , wherein the content of the compound (B) is 70 to 99.99 mass%, with the entire conductive polymer composition being 100 mass%.

[0168]

[12] The conductive polymer composition according to any one of [1] to

[11] , further comprising a dispersant (C).

[0169]

[13] A composition for producing a conductive hard coat, comprising the conductive polymer composition according to any one of [1] to

[12] , a polymerizable oligomer, and a polymerization initiator.

[0170]

[14] A method for producing a conductive hard coat, comprising the steps of applying the conductive hard coat production composition according to

[13] to a substrate to produce a coating film, and irradiating the coating film with ultraviolet light.

[0171]

[15] A composition for producing a conductive adhesive film, comprising the conductive polymer composition according to any one of [1] to

[12] and a polymerization initiator.

[0172]

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

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

[0173]

[17] A composition for producing a conductive release layer, comprising the conductive polymer composition according to any one of [1] to

[12] .

[0174]

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

[17] to a substrate to produce a coating film, and drying the coating film.

[0175]

[19] A conductive cured product obtained by curing the composition for producing a conductive hard coat according to

[13] .

[0176] Examples are shown below, but the present invention should not be construed as being limited to these examples. The analytical instruments and measurement methods used in these examples are listed below. In the following examples and comparative examples, "%" indicating the content is by weight unless otherwise specified.

[0177] [Method for producing conductive hard coat] A PET film (A4160 manufactured by Toyobo) was placed on a tabletop printing tester (K202 Control Coater manufactured by Matsuo Sangyo), and a coating film with a wet film thickness of 18 μm was produced on the PET film using a wire bar. The PET film with the coating film applied was placed in a thermostatic chamber set to 80°C and heated in the atmosphere for 5 minutes, and then irradiated with ultraviolet light in the atmosphere for 1 minute using a tabletop UV curing device (HC-96X manufactured by Sen Special Light Sources) to obtain a conductive hard coat.

[0178] [Method for measuring surface resistance of conductive hard coat and evaluation criteria] The measurement probe (USP) of a surface resistance measuring instrument (Hiresta-UX MCP-HT800, manufactured by Nitto Seiko Analytech) was pressed against the surface of the conductive hard coat prepared in the examples, and the surface resistance (Ω / □) was measured under atmospheric pressure at room temperature. The evaluation results were as follows: a surface resistance of 1.0 × 10 １３ Less than Ω / □ is good, 1.0×10 １３ A value of Ω / □ or more was considered to be defective.

[0179] [Method for producing conductive adhesive film and method for measuring surface resistance value] A curing agent was added to the prepared composition for producing a conductive adhesive, and the mixture was stirred and mixed at 20°C for 30 minutes. The obtained mixture was then applied to a PET film using a Select-Roller / A-Bar (manufactured by OSG System Products) so that the film thickness immediately after application (wet film thickness) was 52 μm, and the film was dried at 80°C for 5 minutes to produce a conductive adhesive film.

[0180] The measurement probe (USP) of a surface resistance measuring instrument (Hiresta-UX MCP-HT800, manufactured by Nitto Seiko Analytech) was pressed against the surface of this conductive adhesive film, and the surface resistance value (Ω / □) was measured under atmospheric pressure at room temperature. It can be said that the lower the surface resistance value of the conductive adhesive film, the higher the antistatic ability. Regarding the evaluation results, the conductive adhesive film had a surface resistance value of 10 １３ If the surface resistance is less than Ω / □, it can be said to be a conductive adhesive film with antistatic properties. １３ Less than Ω / □ is good, 1.0×10 １３ A value of Ω / □ or more was considered to be defective.

[0181] [Dispersant (C)] The following dispersants were used as dispersants (C): Trade name: Hinoact T-6000 (manufactured by Kawaken Fine Chemicals Co., Ltd.) Trade name: Ethreem AD-374M (manufactured by NOF Corporation) Trade name: Ajisper PB821 (manufactured by Ajinomoto Fine-Techno Co., Inc.)

[0182] [Polymerizable Oligomer] The following polymerizable oligomers were used: Trade name UA-1100H (urethane acrylate oligomer, manufactured by Shin-Nakamura Chemical Co., Ltd.) Trade name UN-904 (urethane acrylate oligomer, manufactured by Negami Chemical Industrial Co., Ltd.) Trade name EBECRYL 600 (epoxy acrylate oligomer, manufactured by Daicel Allnex Corporation)

[0183] [Method for producing conductive release layer] A PET film (A4160 manufactured by Toyobo) was placed on a tabletop printing tester (K202 Control Coater manufactured by Matsuo Sangyo), and a coating film having a wet thickness of 6 μm was formed on the PET film using a wire bar, which was made of the composition for producing a conductive release layer prepared in the examples. The PET film coated with the coating film was placed in a thermostatic chamber set to 120 ° C. and heated in the atmosphere for 30 seconds to obtain a conductive release layer.

[0184] [Method for measuring surface resistance of conductive release layer and evaluation criteria] A measurement probe (USP) of a surface resistance measuring instrument (Hiresta-UX MCP-HT800, manufactured by Nitto Seiko Analytech) was pressed against the surface of the conductive release layer prepared in the examples, and the surface resistance (Ω / □) was measured under atmospheric pressure at room temperature. The evaluation results showed that the surface resistance was 1.0 × 10 １３ Less than Ω / □ is good, 1.0×10 １３ A value of Ω / □ or more was considered to be defective.

[0185] Example 1 [Preparation and Evaluation of a Composition Containing a Conductive Polymer] A polythiophene (the self-doped conductive polymer (A) and corresponding to polythiophene (A2)) produced based on the method of Example 2 of JP-A-2019-210356 (R ２ = methyl group, M ＋= trioctylammonium, m = 2. Hereinafter, abbreviated as "polythiophene (a1)." 0.1 g of the solid [Chemical Formula (B)] and 9.9 g of acrylic acid (corresponding to the above-mentioned compound (B)) were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) and acrylic acid at a concentration of 1 wt% (corresponding to a conductive polymer composition according to one embodiment of the present invention). The polythiophene (a1) was uniformly dispersed or dissolved in the acrylic acid, and no precipitate was observed even after settling for 2 hours. The appearance of the obtained composition was evaluated, and the results are shown in Table 1.

[0186] Examples 2 to 22 Compositions containing conductive polymers (corresponding to conductive polymer compositions according to one aspect of the present invention) were prepared and evaluated in the same manner as in Example 1, according to the formulations shown in Table 1 below. The appearances of the obtained compositions were evaluated, and the results are shown in Table 1.

[0187] Example 23 [Preparation and Evaluation of a Composition Containing a Conductive Polymer] 0.1 g of solid polythiophene (a1), 0.2 g of Hinoact T-6000 corresponding to dispersant (C), and 9.7 g of butyl acrylate (corresponding to the above-mentioned compound (B)) were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) at a concentration of 1 wt %, dispersant (C), and butyl acrylate (corresponding to a conductive polymer composition according to one embodiment of the present invention). The polythiophene (a1) was uniformly dispersed or dissolved, and no precipitate was observed even after being allowed to settle for 2 hours. The appearance of the obtained composition was evaluated, and the results are shown in Table 1.

[0188] Examples 24 to 29 Compositions containing conductive polymers (corresponding to conductive polymer compositions according to one aspect of the present invention) were prepared and evaluated in the same manner as in Example 23, using the formulations shown in Table 1 below. The appearances of the obtained compositions were evaluated, and the results are shown in Table 1.

[0189] Example 50 [Preparation and evaluation of a composition containing a conductive polymer] 0.1 g of solid polythiophene (a1), 0.2 g of Esreem AD-374M corresponding to dispersant (C), and 9.7 g of 2-phenoxyethyl acrylate (corresponding to the above-mentioned compound (B)) were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) at a concentration of 1 wt%, dispersant (C), and 2-phenoxyethyl acrylate (corresponding to a conductive polymer composition according to one embodiment of the present invention). The polythiophene (a1) was uniformly dispersed or dissolved, and no precipitate was observed even after being allowed to settle for 2 hours.

[0190] Example 54 [Preparation and Evaluation of a Composition Containing a Conductive Polymer] 0.1 g of solid polythiophene (a1), 1 g of ethanol, and 8.9 g of 2-phenoxyethyl acrylate (corresponding to the above-mentioned compound (B)) were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) at a concentration of 1 wt %, ethanol, and 2-phenoxyethyl acrylate (corresponding to a conductive polymer composition according to one embodiment of the present invention). The polythiophene (a1) was uniformly dispersed or dissolved, and no precipitate was observed even after being allowed to settle for 2 hours.

[0191] Example 55 [Preparation and Evaluation of a Composition Containing a Conductive Polymer] 0.1 g of solid polythiophene (a1), 1 g of toluene, and 8.9 g of 2-phenoxyethyl acrylate (corresponding to the above-mentioned compound (B)) were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) at a concentration of 1 wt %, toluene, and 2-phenoxyethyl acrylate (corresponding to a conductive polymer composition according to one embodiment of the present invention). The polythiophene (a1) was uniformly dispersed or dissolved, and no precipitate was observed even after being allowed to settle for 2 hours.

[0192] Comparative Example 1 A composition was prepared in the same manner as in Example 1, except that 0.1 g of poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) (Aldrich, trade name: Orgacon DRY; hereinafter abbreviated as "PEDOT / PSS") was used instead of 0.1 g of polythiophene (a1). PEDOT / PSS did not dissolve or disperse uniformly in acrylic acid.

[0193] Comparative Example 2 A composition was prepared in the same manner as in Example 3, except that 0.1 g of PEDOT / PSS was used instead of 0.1 g of polythiophene (a1) in Example 3. PEDOT / PSS was not uniformly dissolved or dispersed in 2-hydroxyethyl acrylate.

[0194] Reference Example 1 [Preparation and Evaluation of a Composition Containing a Conductive Polymer] 0.1 g of solid polythiophene (a1), 0.2 g of Esreem AD-374M corresponding to dispersant (C), and 9.7 g of ethanol were mixed and stirred at 20°C for 1 hour to obtain a composition consisting of polythiophene (a1) at a concentration of 1 wt%, dispersant (C), and ethanol. The polythiophene (a1) was uniformly dispersed or dissolved, and no precipitate was observed even after settling for 2 hours.

[0195]

[0196] From the results of the Examples and Comparative Examples in Table 1, it was confirmed that a conductive polymer composition in which the self-doping conductive polymer (A) was uniformly dissolved or dispersed in the compound (B) could be obtained.

[0197] Example 30 [Preparation of a composition for producing a conductive hard coat and evaluation of the conductive hard coat] 0.04 g of solid polythiophene (a1) and 3.96 g of 4-hydroxybutyl acrylate (corresponding to the above-mentioned compound (B); hereinafter abbreviated as "4-HBA") were mixed and stirred at 20°C for 30 minutes to obtain 4 g of a conductive polymer composition according to one embodiment of the present invention.

[0198] 20 g of the polymerizable oligomer UA-1100H, 20 g of a polymerizable monomer, 2-hydroxyethyl acrylate (hereinafter abbreviated as "2-HEA"), 3 g of 1-hydroxycyclohexyl phenyl ketone (corresponding to the above-mentioned polymerization initiator), and 53 g of propylene glycol monomethyl ether (corresponding to the above-mentioned solvent, hereinafter abbreviated as "PGME") were mixed together to obtain 96 g of a polymerizable composition.

[0199] 4 g of the conductive polymer composition and 96 g of the polymerizable composition were mixed to prepare 100 g of a composition for producing a conductive hard coat according to one embodiment of the present invention.

[0200] Using the above-mentioned composition for producing a conductive hard coat, a conductive hard coat was produced according to the above-mentioned [Method for producing a conductive hard coat], and evaluated according to the above-mentioned [Method for measuring the surface resistance of a conductive hard coat and evaluation criteria]. The composition of the prepared composition for producing a conductive hard coat and the obtained evaluation results are shown in Table 2.

[0201] Examples 31 to 38 The same operations as in Example 30 were carried out to prepare compositions for producing conductive hard coats, fabricate conductive hard coats, and evaluate them, except that the composition in Example 30 was changed to the composition shown in Table 2. The obtained evaluation results are shown in Table 2.

[0202] Example 39 A composition for producing a conductive hard coat was prepared, a conductive hard coat was produced, and the results were evaluated in the same manner as in Example 32, except that 20 g of polymerizable oligomer UA-904 was used instead of 20 g of polymerizable oligomer UA-1100H. The evaluation results are shown in Table 2.

[0203] Example 40 A composition for producing a conductive hard coat was prepared, a conductive hard coat was produced, and the conductive hard coat was evaluated in the same manner as in Example 32, except that 10 g of polymerizable oligomer EBECRYL 600 was used instead of 20 g of polymerizable oligomer UA-1100H, and the amount of polymerizable monomer 2-HEA used was changed from 20 g to 30 g. The obtained evaluation results are shown in Table 2.

[0204] Example 41 0.16 g of solid polythiophene (a1) and 15.84 g of 4-HBA were mixed with stirring at 20° C. for 30 minutes to obtain 16 g of a conductive polymer composition according to one embodiment of the present invention.

[0205] 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, 3 g of 1-hydroxycyclohexyl phenyl ketone, 40.4 g of PGME, and 0.06 g of a water-repellent and stain-proofing agent composed of a fluorine compound (Shin-Etsu Chemical Co., Ltd., product name: KY-1203) were mixed to obtain 84 g of a polymerizable composition.

[0206] 16 g of the conductive polymer composition and 84 g of the polymerizable composition were mixed to prepare 100 g of a composition for producing a conductive hard coat according to one embodiment of the present invention.

[0207] Using the above-mentioned composition for producing a conductive hard coat, a conductive hard coat was prepared according to the above-mentioned [Method for preparing a conductive hard coat], and evaluated according to the above-mentioned [Method for measuring the surface resistance value of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0208] Example 42 0.16 g of solid polythiophene (a1), 15.52 g of 2-ethylhexyl acrylate (corresponding to the above compound (B); hereinafter abbreviated as "2-EHA"), and 0.32 g of Esreem AD-374M corresponding to the dispersant (C) were mixed with stirring at 20°C for 30 minutes, to obtain 16 g of a conductive polymer composition according to one embodiment of the present invention.

[0209] 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, 3 g of 1-hydroxycyclohexylphenyl ketone, and 41 g of PGME were mixed to obtain 84 g of a polymerizable composition.

[0210] 16 g of the conductive polymer composition and 84 g of the polymerizable composition were mixed to prepare 100 g of a composition for producing a conductive hard coat according to one embodiment of the present invention.

[0211] Using the above-mentioned composition for producing a conductive hard coat, a conductive hard coat was prepared according to the above-mentioned [Method for preparing a conductive hard coat], and evaluated according to the above-mentioned [Method for measuring the surface resistance value of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0212] Example 43 0.16 g of solid polythiophene (a1), 56.52 g of 2-EHA, and 0.32 g of Esreem AD-374M corresponding to the dispersant (C) were mixed with stirring at 20°C for 30 minutes to obtain 57 g of a conductive polymer composition according to one embodiment of the present invention.

[0213] 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, and 3 g of 1-hydroxycyclohexylphenyl ketone were mixed to obtain 43 g of a polymerizable composition.

[0214] 57 g of the conductive polymer composition and 43 g of the polymerizable composition were mixed to prepare 100 g of a composition for producing a conductive hard coat according to one embodiment of the present invention.

[0215] Using the above-mentioned composition for producing a conductive hard coat, a conductive hard coat was prepared according to the above-mentioned [Method for preparing a conductive hard coat], and evaluated according to the above-mentioned [Method for measuring the surface resistance value of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0216] Comparative Example 3 (Example in which the self-doping type conductive polymer (A) was not used) 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, 3 g of 1-hydroxycyclohexyl phenyl ketone, and 41 g of PGME were mixed to obtain 84 g of a polymerizable composition.

[0217] 16 g of 4-HBA and 84 g of the above polymerizable composition were mixed to prepare 100 g of a composition for producing a hard coat.

[0218] Using the above composition for producing a hard coat, a hard coat was prepared according to the above [Method for preparing a conductive hard coat] and evaluated according to the above [Method for measuring the surface resistance of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0219] Comparative Example 4 (Example in which self-doped conductive polymer (A) was not used) 0.16 g of an ionic liquid (lithium bis(trifluoromethanesulfonyl)imide, manufactured by Tokyo Chemical Industry Co., Ltd.) and 15.84 g of 4-HBA were mixed and stirred at 20° C. for 30 minutes to obtain 16 g of a composition.

[0220] 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, 3 g of 1-hydroxycyclohexylphenyl ketone, and 41 g of PGME were mixed to obtain 84 g of a polymerizable composition.

[0221] 16 g of the above composition and 84 g of the above polymerizable composition were mixed to prepare 100 g of a composition for producing a hard coat.

[0222] Using the above composition for producing a hard coat, a hard coat was prepared according to the above [Method for preparing a conductive hard coat] and evaluated according to the above [Method for measuring the surface resistance of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0223] Comparative Example 5 (Example in which self-doped conductive polymer (A) was not used) 0.16 g of an ionic liquid (lithium bis(trifluoromethanesulfonyl)imide, manufactured by Tokyo Chemical Industry Co., Ltd.) and 56.84 g of 4-HBA were mixed and stirred at 20°C for 30 minutes to obtain 57 g of a composition.

[0224] 20 g of the polymerizable oligomer UA-1100H, 20 g of the polymerizable monomer 2-HEA, and 3 g of 1-hydroxycyclohexylphenyl ketone were mixed to obtain 43 g of a polymerizable composition.

[0225] 57 g of the above composition and 43 g of the above polymerizable composition were mixed to prepare 100 g of a composition for producing a hard coat.

[0226] Using the above composition for producing a hard coat, a hard coat was prepared according to the above [Method for preparing a conductive hard coat] and evaluated according to the above [Method for measuring the surface resistance of a conductive hard coat and evaluation criteria]. The composition of the prepared composition and the obtained evaluation results are shown in Table 2.

[0227]

[0228] As shown in Table 2, the surface resistance of the conductive hard coat films of Examples 30 to 43 was 1.0×10 ９ Ω / □ to 7.0 x 10 １２ Ω / □, which was favorable in that antistatic properties were expected.

[0229] On the other hand, the surface resistance values ​​of the hard coat films of Comparative Examples 3, 4, and 5 (not containing the self-doping conductive polymer (A)) were all 1.0 × 10 １３The resistance was Ω / □ or more, and the evaluation was poor in that antistatic properties could not be expected.

[0230] Example 44 [Preparation of composition for producing conductive adhesive film and evaluation of conductive adhesive film] 0.64 g of solid polythiophene (a1), 20.00 g of 2-EHA, and 1.28 g of Esreem AD-374M corresponding to dispersant (C) were mixed and stirred at 20°C for 30 minutes to obtain 21.92 g of a conductive polymer composition according to one embodiment of the present invention.

[0231] 21.92 g of the above conductive polymer composition, 1.06 g of polymerizable monomer 2-HEA, 0.22 g of the polymerizable monomer methacrylic acid (hereinafter abbreviated as "MAA"), 50 g of ethyl acetate, and 0.06 g of 2,2'-azobisisobutyronitrile (hereinafter abbreviated as "AIBN") as a polymerization initiator were placed in a separable flask and stirred for 1 hour while introducing nitrogen gas. After removing oxygen from the polymerization system in this way, the temperature was raised to 67°C and the reaction was carried out for 5 hours, yielding a composition for producing a conductive adhesive film with a solids concentration of 32 wt%.

[0232] 0.02 g of Karenz MOI as a curing agent was added to 2 g of the composition for producing a conductive adhesive film, and the mixture was stirred and mixed at 20° C. for 30 minutes to obtain a mixed solution. A conductive adhesive film was produced and evaluated according to the above-mentioned [Method for producing a conductive adhesive film and method for measuring surface resistance value]. The composition of the composition for producing a conductive adhesive film and the obtained evaluation results are shown in Table 3. The obtained conductive adhesive film exhibited adhesiveness equivalent to that of the adhesive film of Comparative Example 6 described below.

[0233] Examples 45 to 49 The same operations as in Example 44 were carried out to prepare compositions for producing conductive adhesive films, fabricate conductive adhesive films, and evaluate them, except that the composition in Example 44 was changed to the composition shown in Table 3. The evaluation results obtained are shown in Table 3. Note that all of the obtained conductive adhesive films exhibited adhesiveness equivalent to that of the adhesive film of Comparative Example 6 described below.

[0234] Comparative Example 6 (Example in which self-doped conductive polymer (A) is not used) Without using polythiophene (a1), 20.00 g of 2-EHA, 1.06 g of polymerizable monomer 2-HEA, 0.22 g of polymerizable monomer MAA, 50 g of ethyl acetate, and 0.06 g of AIBN as a polymerization initiator were placed in a separable flask and stirred for 1 hour while introducing nitrogen gas. After removing oxygen from the polymerization system in this way, the temperature was raised to 67°C and the reaction was carried out for 5 hours, and a composition for producing an adhesive film with a solids concentration of 32 wt% was obtained.

[0235] 0.02 g of Karenz MOI as a curing agent was added to 2 g of the above-mentioned composition for producing an adhesive film, and the mixture was stirred and mixed at 20° C. for 30 minutes to obtain a mixed solution. An adhesive film was produced and evaluated according to the above-mentioned [Method for producing a conductive adhesive film and method for measuring surface resistance value]. The composition of the composition for producing an adhesive film and the obtained evaluation results are shown in Table 3. The obtained adhesive film showed good adhesion to the PET film substrate.

[0236] Comparative Example 7 (Example in which the self-doped conductive polymer (A) was not used) 0.64 g of an ionic liquid (lithium bis(trifluoromethanesulfonyl)imide, manufactured by Tokyo Chemical Industry Co., Ltd.) instead of polythiophene (a1) and 10.53 g of 2-EHA were mixed and stirred at 20°C for 30 minutes to obtain 11.17 g of a composition.

[0237] 11.17 g of the above composition, 10.53 g of polymerizable monomer 2-HEA, 0.22 g of polymerizable monomer MAA, 50 g of ethyl acetate, and 0.06 g of AIBN as a polymerization initiator were placed in a separable flask and stirred for 1 hour while introducing nitrogen gas. After removing oxygen from the polymerization system in this way, the temperature was raised to 67°C and the reaction was carried out for 5 hours, yielding a composition for producing an adhesive film with a solids concentration of 32 wt%.

[0238] 0.02 g of Karenz MOI as a curing agent was added to 2 g of the above-mentioned composition for producing an adhesive film, and the mixture was stirred and mixed for 30 minutes at 20° C. Using the resulting mixture, an adhesive film was produced and evaluated according to the above-mentioned [Method for producing a conductive adhesive film and method for measuring surface resistance value]. The composition of the composition for producing an adhesive film and the obtained evaluation results are shown in Table 3.

[0239]

[0240] As shown in Table 3, the surface resistance of the conductive adhesive films of Examples 44 to 49 was 8.4 × 10 １０ Ω / □~2.3×10 １２ Ω / □, which was favorable in that antistatic properties were expected.

[0241] On the other hand, the surface resistance values ​​of the adhesive films of Comparative Examples 6 and 7 (not containing the self-doping conductive polymer (A)) were both 1.0 × 10 １３ The resistance was Ω / □ or more, and the evaluation was poor in that antistatic properties could not be expected.

[0242] Example 51 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of LTC310 (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.30 g of the conductive polymer composition prepared in Example 50 above were mixed and stirred for 5 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 (manufactured by Toray Dow Co., Ltd.) was added and stirred for 15 minutes to prepare a composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, a conductive release layer according to one embodiment of the present invention was produced using the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １１ The resistivity was Ω / □ (good). The obtained conductive release layer also exhibited releasability equivalent to that of the release layer of Comparative Example 8 described below.

[0243] Example 52 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of SRX211 (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.30 g of the conductive polymer composition prepared in Example 50 above were mixed and stirred for 15 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 (manufactured by Toray Dow Co., Ltd.) was added and stirred for 15 minutes to prepare a composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, a conductive release layer according to one embodiment of the present invention was produced using the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １１The resistivity was Ω / □ (good). The obtained conductive release layer also exhibited releasability equivalent to that of the release layer of Comparative Example 8 described below.

[0244] Example 53 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of LTC750A (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.15 g of the conductive polymer composition prepared in Example 50 above were mixed and stirred for 15 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 (manufactured by Toray Dow Co., Ltd.) was added and stirred for 15 minutes to prepare a composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, a conductive release layer according to one embodiment of the present invention was produced using the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １１ The resistivity was Ω / □ (good). The obtained conductive release layer also exhibited releasability equivalent to that of the release layer of Comparative Example 8 described below.

[0245] Example 56 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of LTC310 (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.30 g of the conductive polymer composition prepared in Example 54 above were mixed and stirred for 15 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 (manufactured by Toray Dow Co., Ltd.) was added and stirred for 15 minutes to prepare a composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, a conductive release layer according to one embodiment of the present invention was produced using the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １１ The resistivity was Ω / □ (good). The obtained conductive release layer also exhibited releasability equivalent to that of the release layer of Comparative Example 8 described below.

[0246] Example 57 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of LTC310 (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.30 g of the conductive polymer composition prepared in Example 55 above were mixed and stirred for 15 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 (manufactured by Toray Dow Co., Ltd.) was added and stirred for 15 minutes to prepare a composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, a conductive release layer according to one embodiment of the present invention was produced using the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １１ The resistivity was Ω / □ (good). The obtained conductive release layer also exhibited releasability equivalent to that of the release layer of Comparative Example 8 described below.

[0247] Reference Example 2 [Preparation of a composition for producing a conductive release layer and evaluation of the conductive release layer] 0.17 g of LTC310 (manufactured by Toray Dow Co., Ltd.) as a release agent, 4.83 g of methyl ethyl ketone, and 0.30 g of the conductive polymer composition prepared in Reference Example 1 above were mixed and stirred for 15 minutes. Next, 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 composition for producing a conductive release layer according to one embodiment of the present invention. After 2 hours, the solution was used to produce a conductive release layer according to one embodiment of the present invention according to the above [Method for producing a conductive release layer].

[0248] Comparative Example 8 (Example in which the self-doped conductive polymer (A) is not used) 0.17 g of LTC310 manufactured by Toray Dow Co., Ltd. as a release agent and 4.83 g of methyl ethyl ketone were mixed and stirred for 15 minutes. Next, 0.0033 g of cured platinum catalyst SRX212 manufactured by Toray Dow Co., Ltd. was added and stirred for 15 minutes to prepare a composition for producing a release layer. After 2 hours, a release layer was produced from the solution according to the above [Method for producing a conductive release layer] and [Method for measuring the surface resistance of a conductive release layer and evaluation criteria], and the surface resistance was measured. １３ The value was Ω / □ or more (poor). Furthermore, when the releasability of the obtained release layer from the PET film substrate was evaluated, it was found to exhibit good releasability with a small peel force.

[0249]

[0250] As shown in Table 4, the surface resistance of the conductive release layers of Examples 51 to 53 and 56 to 57 was 1.0 × 10 １１ Ω / □, which was favorable in that antistatic properties were expected.

[0251] On the other hand, the surface resistance of the release layer of Comparative Example 8 (not containing the self-doping conductive polymer (A)) was 1.0 × 10 １３ The resistance was Ω / □ or more, and the evaluation was poor in that antistatic properties could not be expected.

[0252] The conductive polymer composition according to one aspect of the present invention can be effectively used as a component of, for example, a composition for producing a conductive hard coat, a composition for producing a conductive adhesive film, or a composition for producing a conductive release layer, and can impart conductivity and antistatic properties to various resins, including hard coat films, adhesive films, and release layers.

[0253] Furthermore, since a volatile solvent is not necessarily required, it is also useful from the viewpoint of improving productivity and reducing environmental load.

Claims

1. Self-doped conductive polymer (A) and CR ５ ２ =CR ６ ２ (R ５ , R ６ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an organic group, and the two organic groups may be bonded to each other to form a ring structure.

2. The conductive polymer composition according to claim 1, wherein the self-doping type conductive polymer (A) is a polythiophene 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 following general formula (1) and a structural unit represented by the following general formula (2): [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 14 carbon atoms and having at least one substituent selected from the group consisting of a sulfonic acid group and a phosphonic acid group.] 3. The conductive polymer composition according to claim 1, wherein the self-doping conductive polymer (A) is a polythiophene (A1) containing at least two or more structural units 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 the general formula (3), M ＋ represents a hydrogen ion, an alkali metal ion, a conjugate acid of an amine compound, or a quaternary ammonium cation. ２ represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a halogen atom; m represents an integer of 1 to 6, and n represents 0 or 1.

4. The conductive polymer composition according to claim 3, wherein in the general formulas (3) and (4), m is 2 or 3.

5. In the general formulas (3) and (4), the R ２ The conductive polymer composition according to claim 3 , wherein is a methyl group.

6. In the general formula (3), ＋ is a conjugated acid of an amine compound having a total of 4 to 30 carbon atoms, or a quaternary ammonium cation having a total of 4 to 30 carbon atoms.

7. The conductive polymer composition according to claim 1, wherein the compound (B) has a molecular weight of 60 to 700.

8. The conductive polymer composition according to claim 1, wherein the compound (B) is an acrylic acid compound, a methacrylic acid compound, a maleimide compound, an aromatic vinyl compound, or a vinyl acetate monomer.

9. The conductive polymer composition according to claim 1, wherein the compound (B) is an acrylic acid compound having a total carbon number of 3 to 13, a methacrylic acid compound having a total carbon number of 4 to 14, a maleimide compound having a total carbon number of 4 to 13, an aromatic vinyl compound having a total carbon number of 8 to 14, or a vinyl acetate monomer.

10. The conductive polymer composition according to claim 1, wherein the compound (B) is an acrylate compound having a total carbon number of 3 to 13, a methacrylate compound having a total carbon number of 4 to 14, an acrylamide compound having a total carbon number of 3 to 13, or a methacrylamide compound having a total carbon number of 4 to 14.

11. The conductive polymer composition according to claim 1, wherein the content of the compound (B) is 70 to 99.99 mass % relative to 100 mass % of the entire conductive polymer composition.

12. The conductive polymer composition according to claim 1, further comprising a dispersing agent (C).

13. A composition for producing a conductive hard coat, comprising the conductive polymer composition according to any one of claims 1 to 12, a polymerizable oligomer, and a polymerization initiator.

14. A method for producing a conductive hard coat, comprising the steps of: applying the composition for producing a conductive hard coat according to claim 13 to a substrate to produce a coating film; and irradiating the coating film with ultraviolet light.

15. A composition for producing a conductive adhesive film, comprising the conductive polymer composition according to any one of claims 1 to 12 and a polymerization initiator.

16. A method for producing a conductive adhesive film, comprising the steps of: applying the composition for producing a conductive adhesive film according to claim 15 to a substrate to produce a coating film; and heating the coating film.

17. A composition for producing a conductive release layer, comprising the conductive polymer composition according to any one of claims 1 to 12.

18. A method for producing a conductive release layer, comprising the steps of applying the composition for producing a conductive release layer according to claim 17 to a substrate to produce a coating film, and drying the coating film.

19. A conductive cured product obtained by curing the composition for producing a conductive hard coat according to claim 13.