Organic transistor

Abstract

An organic transistor (1001) according to the present disclosure has a gate electrode (3), a source electrode (5), a drain electrode (6), an organic semiconductor film (1), and a first gate insulating film (4) that is in contact with the organic semiconductor film (1). The organic semiconductor film (1) contains a conjugated polymer which is expressed by a structural unit represented by general formula (2) and a structural unit represented by general formula (3). The interface energy between the first gate insulating film (4) and the organic semiconductor film is 2.0 mJ / m2 or less.　(In the formulae, A and B each represent an aromatic ring linking group which may be substituted, and R1, R2, R3 and R4 each represent an alkyl group. R5 and R6 each represent a hydrogen atom, a fluorine atom or an alkyl group.)　(In the formulae, X represents a heteroaromatic ring linking group.)

Description

organic transistor

[0001] The present invention relates to an organic transistor.

[0002] Organic semiconductor devices, such as organic transistors, have attracted attention in recent years because of their advantages over inorganic semiconductor devices, such as energy saving, low cost, and flexibility.

[0003] This organic semiconductor device is composed of several types of materials such as an organic semiconductor layer, a substrate, an insulating layer, and electrodes, and among these, the organic semiconductor layer, which is responsible for the movement of charge carriers, plays a central role in the device.

[0004] Since the performance of organic semiconductor devices depends on the carrier mobility of the organic material that constitutes the organic semiconductor layer, the development of organic materials that provide high carrier mobility is desired.

[0005] Commonly known methods for producing organic semiconductor layers include vacuum deposition, in which organic materials are vaporized under high temperature and vacuum, and coating, in which an organic material is dissolved in an appropriate solvent and the resulting solution is coated. Coating can be performed using printing technology without using high temperature and high vacuum conditions, and is therefore considered an economically preferable process. Therefore, organic semiconductor layers with high coatability and excellent carrier mobility are desired.

[0006] Generally, there is a trade-off between carrier mobility and performance variation, and while highly crystalline small molecule semiconductors tend to provide high mobility, they also tend to have large performance variations.

[0007] Polymer semiconductors are less susceptible to the effects of the crystallinity of the compound and the film quality after coating and deposition, resulting in little variation, but there is a demand for improved mobility, and realizing coated organic TFTs with high carrier mobility is essential for device applications.

[0008] Furthermore, organic semiconductors are desired to have high heat resistance, high atmospheric stability, and high solubility in addition to high carrier mobility. However, there are few reported examples of compounds that have all of these properties. For example, the donor-acceptor polymer semiconductor described in Patent Document 1 is known, but further improvement in mobility is required.

[0009] Among these physical properties, heat resistance (melting point or glass transition temperature), atmospheric stability (ionization potential), and solubility (solubility in organic solvents) are inherent to each compound, while mobility is known to vary depending on the crystalline state of the compound and the device structure.

[0010] Japanese Patent Application Laid-Open No. 2023-008031

[0011] The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic transistor having high carrier mobility.

[0012] As a result of extensive investigations to solve the above problems, the present inventors have found that a polymer semiconductor organic transistor with high carrier mobility can be formed based on the difference in interfacial energy between a first gate insulating film and an organic semiconductor film, and have thus completed the present invention.

[0013] That is, the present invention is as follows.

[0014] [1] A semiconductor device comprising a gate electrode, a source electrode, a drain electrode, and an organic semiconductor film, and further comprising a first gate insulating film in contact with the organic semiconductor film, or a first gate insulating film in contact with the organic semiconductor film and a second gate insulating film not in contact with the organic semiconductor film, wherein the organic semiconductor film contains a conjugated polymer composed of a structural unit represented by the following general formula (2) and a structural unit represented by the following general formula (3), and wherein the interface energy between the first gate insulating film and the organic semiconductor film is 2.0 mJ / m ２ An organic transistor characterized by: (In the formula, A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (wherein X represents a divalent heteroaromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms).

[0015] The organic transistor according to one aspect of the present invention has high carrier mobility.

[0016] 1A and 1B are diagrams illustrating a cross-sectional structure of an organic transistor according to an embodiment of the present invention;

[0017] The present invention will be described in detail below.

[0018] [Organic Transistor] An organic transistor according to one embodiment of the present invention includes a gate electrode, a source electrode, a drain electrode, and an organic semiconductor film. The organic transistor further includes a first gate insulating film in contact with the organic semiconductor film and a second gate insulating film not in contact with the organic semiconductor film. However, the second gate insulating film may be present or absent.

[0019] Examples of gate electrodes used in an organic transistor according to one embodiment of the present invention include inorganic electrodes such as aluminum, gold, silver, copper, highly doped silicon, tin oxide, indium oxide, indium tin oxide, chromium, titanium, tantalum, chromium, graphene, and carbon nanotubes, and organic electrodes such as doped conductive polymers (PEDOT-PSS). Among these, inorganic electrodes are preferred due to their good conductivity, and silver or gold is more preferred. There are no particular limitations on the materials for the source and drain electrodes used in an organic transistor according to one embodiment of the present invention. Materials similar to those used for the gate electrode can be used. These materials may be the same as or different from the gate electrode material, or different materials may be stacked. Furthermore, these electrode materials can be surface-treated to increase carrier injection efficiency. Examples of surface treatment agents for electrode materials include benzenethiol and pentafluorobenzenethiol.

[0020] When performing the surface treatment of an electrode, the surface treatment agent may be diluted with a solvent before use. The solvent to be used for dilution is not particularly limited, and examples thereof include alcohol-based solvents such as methanol, ethanol, and 2-propanol; halogen-based solvents such as o-dichlorobenzene, chlorobenzene, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, and chloroform; ether-based solvents such as THF (tetrahydrofuran) and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, and mesitylene; ester-based solvents such as ethyl acetate and γ-butyrolactone; and amide-based solvents such as N,N-dimethylformamide and N-methylpyrrolidone.

[0021] (Interfacial Energy) The first gate insulating film used in the organic transistor according to one embodiment of the present invention has an interfacial energy between the gate insulating film and the organic semiconductor film of 2.0 mJ / m ２ or less, preferably 1.5 mJ / m ２ More preferably, it is 1.0 mJ / m or less. ２ or less, more preferably 0.5 mJ / m ２ By setting the interfacial energy within the above range, the adhesion between the first gate insulating film and the organic semiconductor film is improved, and the mobility in the organic transistor is improved.

[0022] In one embodiment of the present invention, the interfacial energy between the first gate insulating film and the organic semiconductor film is calculated by the following formula (a).

[0023] gamma １２ = γ １ +γ ２ -2 (γ １ ｄ gamma ２ ｄ ) １／２ -2 (γ １ ｐ gamma ２ ｐ ) １／２ (a) (where γ １２ is the interfacial energy, γ １ is the surface energy of the first gate insulating film, γ １ ｄ is the dispersion force of the first gate insulating film, γ１ ｐ is the polar component of the first gate insulating film, γ ２ is the surface energy of the organic semiconductor film, γ ２ ｄ is the dispersion force of the organic semiconductor film, γ ２ ｐ indicates the polar component of the organic semiconductor film. These values ​​can be calculated by the Owens-Wendt method using thin films of the first gate insulating film and the organic semiconductor film, measuring the contact angles of water and iodomethane by the θ / 2 method.

[0024] (Gate insulating film) In one embodiment of the present invention, the material used for the gate insulating film is not particularly limited. Specific examples include inorganic insulating layers such as silicon oxide, silicon nitride, aluminum oxide, aluminum nitride, titanium oxide, tantalum dioxide, tantalum pentoxide, indium tin oxide, tin oxide, vanadium oxide, barium titanate, and bismuth titanate; polyethylene terephthalate, polyethylene naphthalate, polymethyl methacrylate, polymethyl acrylate, polyethylene, polypropylene, polystyrene, cyclic polyolefin, polyimide, polycarbonate, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), poly(diisopropyl maleate), polyether sulfone, polyphenylene sulfide, and cellulose. Examples of the polymer include triacetate, polycyclopentane, polyalkylnorbornene, polycyclohexane-ethylene copolymer, polyfluorinated cyclopentane, CYTOP (trademark), polyfluorinated cyclohexane, polyfluorinated cyclohexane-ethylene copolymer, Parylene N (trademark), Parylene C (trademark), Parylene D (trademark), Parylene HT (trademark), Parylene C-UVF (trademark), cycloolefin copolymers such as APEL (trademark) and TOPAS (trademark), fluororesins containing a repeating unit represented by the following general formula (105) and a repeating unit represented by the following general formula (106), and resins containing a repeating unit represented by the following general formula (107) and a repeating unit represented by the following general formula (108). Among these, in terms of good insulating properties, polystyrene, Parylene C (trademark), cycloolefin copolymer, fluororesin containing a repeating unit represented by the following general formula (105) and a repeating unit represented by the following general formula (106), and resin containing a repeating unit represented by the following general formula (107) and a repeating unit represented by the following general formula (108) are more preferred, and polystyrene, cycloolefin copolymer, fluororesin containing a repeating unit represented by the following general formula (105) and a repeating unit represented by the following general formula (106), and resin containing a repeating unit represented by the following general formula (107) and a repeating unit represented by the following general formula (108) are particularly preferred.

[0025] (Repeating unit represented by general formula (105)) In general formula (105), R ３ａ represents a hydrogen atom or a methyl group.

[0026] In general formula (105), L １ represents a single bond or a divalent linking group. １ The divalent linking group in is preferably a divalent linking group combining at least two groups selected from the group consisting of a linear alkylene group having 1 to 10 carbon atoms, a branched alkylene group having 3 to 10 carbon atoms, a cyclic alkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms, an ether group (—O—), a carbonyl group (—C(═O)—), and an imino group (—NH—). This makes it possible to form a flat, crack-free film.

[0027] Specific examples of the linear alkylene group having 1 to 10 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, and a decylene group.

[0028] Specific examples of the branched alkylene group having 3 to 10 carbon atoms include a dimethylmethylene group, a methylethylene group, a 2,2-dimethylpropylene group, and a 2-ethyl-2-ethylpropylene group.

[0029] Specific examples of the cyclic alkylene group having 3 to 10 carbon atoms include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclooctylene group, a cyclodecylene group, an adamantane-diyl group, a norbornane-diyl group, and an exo-tetrahydrodicyclopentadiene-diyl group, and among these, a cyclohexylene group is preferable.

[0030] Specific examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a xylylene group, a biphenylene group, a naphthylene group, and a 2,2'-methylenebisphenyl group, and among these, a phenylene group is preferred.

[0031] Among these divalent linking groups, an ester bond (—C(═O)O—) formed by combining a carbonyl group and an ether group, or a linking group formed by combining a phenylene group and an ether group is more preferable, and (—C(═O)O—) is even more preferable.

[0032] In general formula (105), A represents an m-valent linking group. A may be an m-valent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, since this improves the solubility of the resulting resin in organic solvents and fluorine-containing solvents.

[0033] Examples of the substituent that the m-valent hydrocarbon group A may have include an alkyl group, an alkoxy group, a halogen atom, and a hydroxyl group.

[0034] The alkyl group is preferably, for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms; more preferably, an alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, or a cyclohexyl group; still more preferably, an alkyl group having 1 to 4 carbon atoms; and particularly preferably, a methyl group or an ethyl group.

[0035] Examples of the alkoxy group include alkoxy groups having a linear or branched alkyl group having 1 to 16 carbon atoms, such as methoxy, ethoxy, n-propoxy, n-butoxy, isobutoxy, n-pentyloxy, n-hexyloxy, isohexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, n-dodecyloxy, n-tetradecyloxy, 2-ethylhexyloxy, 3-ethylheptyloxy, and 2-hexyldecyloxy groups, and groups selected from the group consisting of methoxy, ethoxy, n-propoxy, n-butoxy, isobutoxy, n-pentyloxy, n-hexyloxy, isohexyloxy, n-heptyloxy, and n-octyloxy groups are particularly preferred.

[0036] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms and chlorine atoms being preferred.

[0037] Among these, the m-valent hydrocarbon group A is preferably one type of linking group selected from the group consisting of the following general formulae (a-1) to (a-4). In the general formulae (a-1) to (a-4), *L represents L in the general formula (105). １ The * before the carbon atom represents the bonding position with the oxygen atom constituting the ester group in the general formula (105).

[0038] For reasons of ease of reaction in monomer synthesis, the m-valent hydrocarbon group A is preferably a trivalent linking group of one type selected from the group consisting of general formula (a-1), general formula (a-2), and general formula (a-3), more preferably a trivalent linking group of general formula (a-1) or general formula (a-2), and even more preferably a trivalent linking group of general formula (a-1).

[0039] In general formula (105), R ３ｂ , R ３ｃ , R ３ｄ , R ３ｅ and R ３ｆ may be the same or different and represent one member of the group consisting of a hydrogen atom, a halogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a linear halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a cyano group, and an amino group.

[0040] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms and chlorine atoms being preferred.

[0041] As the linear alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferred, and specific examples include a methyl group, an ethyl group, and an n-propyl group, and among these, a methyl group or an ethyl group is preferred.

[0042] As the branched alkyl group having 3 to 20 carbon atoms, an alkyl group having 3 to 6 carbon atoms is preferred, and specific examples include an isopropyl group and a tert-butyl group.

[0043] As the cyclic alkyl group having 3 to 20 carbon atoms, an alkyl group having 3 to 6 carbon atoms is preferred, and specific examples include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group, with a cyclohexyl group being particularly preferred.

[0044] As the linear halogenated alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms is preferred. Specific examples include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, and a perfluorobutyl group, and among these, a trifluoromethyl group is preferred.

[0045] As the alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms is preferable, and specific examples include a methoxy group, an ethoxy group, an n-butoxy group, and a methoxyethoxy group.

[0046] As the aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms is preferred. Specific examples include a phenyl group, an α-methylphenyl group, and a naphthyl group, with a phenyl group being particularly preferred.

[0047] As the aryloxy group having 6 to 20 carbon atoms, an aryloxy group having 6 to 12 carbon atoms is preferred. Specific examples include a phenyloxy group and a 2-naphthyloxy group, and among these, a phenyloxy group is preferred.

[0048] The amino group may be, for example, a primary amino group (—NH ２ ), secondary amino groups such as a methylamino group; and tertiary amino groups such as a dimethylamino group, a diethylamino group, a dibenzylamino group, and groups in which the nitrogen atom of a nitrogen-containing heterocyclic compound (e.g., pyrrolidine, piperidine, piperazine, etc.) serves as a bonding bond.

[0049] R ３ｂ , R ３ｃ , R ３ｄ , R ３ｅ and R ３ｆis preferably a hydrogen atom, an alkyl group, a halogen atom, or a linear halogenated alkyl group having 1 to 20 carbon atoms, and more preferably a hydrogen atom, in order to further increase the solubility in a fluorine-based solvent, photocurability, and liquid repellency of the fluorine-based resin.

[0050] Specific examples of the repeating unit represented by general formula (105) (hereinafter, also referred to as repeating unit B) include repeating units B-1 to B-26 shown below, of which B-1 to B-16 are preferred, with B-1, B-2, B-13, and B-16 being particularly preferred. In the following formula, Me represents a methyl group, Et represents an ethyl group, and Pr represents an isopropyl group.

[0051] (Repeating unit represented by general formula (106)) In general formula (106), R ３ｈ represents a hydrogen atom or a methyl group.

[0052] In general formula (106), L ２ represents a single bond or a divalent linking group. ２ The divalent linking group in is preferably a divalent linking group formed by combining at least two groups selected from the group consisting of a linear alkylene group having 1 to 10 carbon atoms, a branched alkylene group having 3 to 20 carbon atoms, a cyclic alkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 12 carbon atoms, an ether group (—O—), a carbonyl group (—C(═O)—), or an imino group (—NH—). This allows for the formation of a flat, crack-free film.

[0053] Specific examples of the linear alkylene group having 1 to 10 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, and a decylene group.

[0054] Specific examples of the branched alkylene group having 3 to 10 carbon atoms include a dimethylmethylene group, a methylethylene group, a 2,2-dimethylpropylene group, and a 2-ethyl-2-ethylpropylene group.

[0055] Specific examples of the cyclic alkylene group having 3 to 10 carbon atoms include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclooctylene group, a cyclodecylene group, an adamantane-diyl group, a norbornane-diyl group, and an exo-tetrahydrodicyclopentadiene-diyl group, and among these, a cyclohexylene group is preferable.

[0056] Specific examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a xylylene group, a biphenylene group, a naphthylene group, and a 2,2'-methylenebisphenyl group, and among these, a phenylene group is preferred.

[0057] Among these divalent linking groups, an ester bond (—C(═O)O—) formed by combining a carbonyl group and an ether group, or a linking group formed by combining a phenylene group and an ether group is more preferable, and (—C(═O)O—) is even more preferable.

[0058] In general formula (106), Rf １ represents one of the group consisting of a linear fluoroalkyl group having 1 to 15 carbon atoms, a branched fluoroalkyl group having 3 to 15 carbon atoms, or a cyclic fluoroalkyl group having 3 to 15 carbon atoms.

[0059] Rf １ is a fluoroalkyl group, the fluorine-based resin according to one aspect of the present invention exhibits affinity with fluorine-based solvents and liquid repellency.

[0060] Rf １ When Rf is a linear fluoroalkyl group, specific examples of Rf １ Examples of L include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or an alkyl group having 10 to 14 carbon atoms, each of which is substituted with a fluorine atom. ２ Rf in １ When the bonding element to Rf is oxygen, １ The substitution position of the fluorine atom in ２ It may be on a carbon atom other than the carbon atom directly bonded to oxygen.

[0061] Rf１ When Rf is a linear fluoroalkyl group, １ is preferably a group represented by the following general formula (109).

[0062] In the general formula (109), * represents L in the general formula (106). ２ represents the bonding position with

[0063] In the general formula (109), X is a hydrogen atom or a fluorine atom.

[0064] In the general formula (109), y is an integer of 1 to 4, preferably 1 or 2.

[0065] In the general formula (109), z is an integer of 1 to 14, preferably 2 to 10, and more preferably 4 to 8.

[0066] Rf １ When is a group represented by general formula (109), the synthesis of a monomer that serves as a raw material for the repeating unit represented by general formula (106) becomes easier.

[0067] Rf １ When Rf is a branched fluoroalkyl group, specific Rf １ Examples of such groups include a 1,1,1,3,3,3-hexafluoroisopropyl group, a 1-(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl group, a 1,1-bis(trifluoromethyl)-2,2,2-trifluoroethyl group, and a 1,1-bis(trifluoromethyl)ethyl group.

[0068] Rf １ When Rf is a cyclic fluoroalkyl group, specific Rf １ Examples of such groups include a 1,2,2,3,3,4,4,5,5-nonafluorocyclopentane group and a 1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexane group.

[0069] The repeating unit represented by the general formula (106) is preferably a repeating unit represented by the following general formula (110):

[0070] In general formula (110), Rj represents either a hydrogen atom or a methyl group.

[0071] In the general formula (110), X is a hydrogen atom or a fluorine atom.

[0072] In the general formula (110), y is an integer of 1 to 4, preferably 1 or 2.

[0073] In the general formula (110), z is an integer of 1 to 14, preferably 2 to 10, and more preferably 4 to 8.

[0074] Specific examples of the repeating unit containing a fluorine atom include one type selected from the group consisting of repeating units represented by the following formulae (C-1) to (C-33).

[0075] One of the group consisting of repeating units represented by the formulae (C-1) to (C-33) is preferred, one of the group consisting of repeating units represented by the formulae (C-9) to (C-33) is more preferred, and one of the group consisting of repeating units represented by the formulae (C-14) to (C-21) or the group consisting of repeating units represented by the formulae (C-27) to (C-33) is particularly preferred.

[0076] (Repeating unit represented by general formula (107)) In general formula (107), R ｉ represents a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom.

[0077] R in general formula (107) ｉ The C1 to C6 alkyl group in is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.

[0078] In general formula (107), S １ represents —O— or —C(O)—.

[0079] In the general formula (107), p represents 0 or 1, with 0 being preferred.

[0080] In general formula (107), A １ represents a C6 to C19 aryl group.

[0081] A in general formula (107) １ The C6 to C19 aryl group in is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, an anthryl group, and a biphenyl group, with a phenyl group being preferred.

[0082] In the general formula (107), Y represents a halogen atom, a cyano group, a nitro group, a carboxyalkyl group, an alkyl ether group, an aryl ether group, a C1 to C18 alkyl group, a fluoroalkyl group, or a cycloalkyl group.

[0083] The halogen atom in Y in the general formula (107) is not particularly limited, and examples thereof include a chlorine atom, a fluorine atom, and a bromine atom.

[0084] The carboxyalkyl group represented by Y in the general formula (107) is not particularly limited, and examples thereof include a carboxymethyl group (—COOCH ３ ), carboxyethyl group (-COOCH ２ CH ３ ), carboxypropyl group (-COOCH ２ CH ２ CH ３ etc.)

[0085] The alkyl ether group for Y in the general formula (107) is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, and a butoxy group.

[0086] The aryl ether group for Y in the general formula (107) is not particularly limited, and examples thereof include a phenoxy group, a p-methylphenoxy group, a p-ethylphenoxy group, and a p-methoxyphenoxy group.

[0087] The C1 to C18 alkyl group represented by Y in the general formula (107) is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.

[0088] The fluoroalkyl group for Y in the general formula (107) is not particularly limited, and examples thereof include a 1,1,1-trifluoroethyl group, a 1,1,1,2,2-pentafluoropropyl group, a 1,1,1,2,2,3,3-heptafluorobutyl group, a trifluoromethyl group, and a pentafluoroethyl group.

[0089] The cycloalkyl group for Y in the general formula (107) is not particularly limited, and examples thereof include a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0090] In the general formula (107), k represents an integer of 0 to (s-1), preferably 0. １ represents the number of carbon atoms that make up the group.

[0091] (Repeating unit represented by general formula (108)) In general formula (108), R ２Ａ represents a hydrogen atom or a C1-C6 alkyl group, preferably a hydrogen atom.

[0092] R in general formula (108) ２Ａ The C1 to C6 alkyl group in is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.

[0093] In general formula (108), S ２ represents —O— or —C(O)—.

[0094] In the general formula (108), q represents 0 or 1, with 0 being preferred.

[0095] In general formula (108), A ２ represents a C6 to C19 aryl group.

[0096] A in general formula (108) ２ The C6 to C19 aryl group in is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, an anthranyl group, and a biphenyl group, with a phenyl group being preferred.

[0097] In the general formula (108), Y represents a substituent similar to the substituent defined in the formula (1).

[0098] In the general formula (108), m represents an integer of 1 to (rj-1), where r is A ２ represents the number of carbon atoms constituting the alkyl group, and j represents an integer of 0 to (r-2). m is preferably 1, and j is preferably 0.

[0099] In the general formula (108), Z represents at least one organic group selected from the formulae (A) to (D), with (A) being preferred.

[0100] In formulas (A) to (D), R ２ｂ and R ３ｂ each independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, an aryl group, or a carboxyalkyl group, preferably a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, more preferably a hydrogen atom; R ４ ~R ２８ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxyalkyl group, an alkyl ether group, an aryl ether group, a C1 to C18 alkyl group, a fluoroalkyl group, or a cycloalkyl group, and among these, a halogen atom, a cyano group, a nitro group, a carboxyalkyl group, or a fluoroalkyl group is preferred, and a halogen atom, a nitro group, or a fluoroalkyl group is more preferred.

[0101] R in formula (A) to formula (D) ２ｂ and R ３ｂ The halogen atom in formula (A) to formula (D) is not particularly limited, and examples thereof include a chlorine atom, a fluorine atom, and a bromine atom. ２ｂ and R ３ｂ The C1 to C6 alkyl group in is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.

[0102] R in formula (A) to formula (D) ２ｂ and R ３ｂ The aryl group in is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, an anthryl group, and a biphenyl group.

[0103] R in formula (A) to formula (D) ２ｂ and R３ｂ The carboxyalkyl group in is not particularly limited, and examples thereof include a carboxymethyl group (—COOCH ３ ), carboxyethyl group (-COOCH ２ CH ３ ), carboxypropyl group (-COOCH ２ CH ２ CH ３ etc.)

[0104] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The halogen atom in is not particularly limited, and examples thereof include a chlorine atom, a fluorine atom, and a bromine atom, with a chlorine atom and a fluorine atom being preferred.

[0105] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The carboxyalkyl group in is not particularly limited, and examples thereof include a carboxymethyl group (—COOCH ３ ), carboxyethyl group (-COOCH ２ CH ３ ), carboxypropyl group (-COOCH ２ CH ２ CH ３ etc.)

[0106] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The alkyl ether group in is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, and a butoxy group.

[0107] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The aryl ether group in is not particularly limited, and examples thereof include a phenoxy group, a p-methylphenoxy group, a p-ethylphenoxy group, and a p-methoxyphenoxy group.

[0108] R in formula (A) to formula (D) ４ｂ ~R ２８ｂThe C1 to C18 alkyl group in 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 n-hexyl group, an n-decyl group, and an n-octadecyl group.

[0109] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The fluoroalkyl group in is not particularly limited, and examples thereof include a 1,1,1-trifluoroethyl group, a 1,1,1,2,2-pentafluoropropyl group, a 1,1,1,2,2,3,3-heptafluorobutyl group, a trifluoromethyl group, a pentafluoroethyl group, etc., with a trifluoromethyl group being preferred.

[0110] R in formula (A) to formula (D) ４ｂ ~R ２８ｂ The cycloalkyl group in is not particularly limited, and examples thereof include a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0111] Specific examples of the organic group represented by formula (A) include the following: Specific examples of the organic group represented by formula (B) include the following: Specific examples of the organic group represented by formula (C) include the following: Specific examples of the organic group represented by formula (D) include the following:

[0112] When the organic transistor according to one embodiment of the present invention includes a second gate insulating film, the material used for the first gate insulating film and the material used for the second gate insulating film may be the same material or different materials.

[0113] The cycloolefin copolymer preferably has a structure represented by the following general formula (4z-1) or (4z-2), and from the viewpoint of high mobility, a structure represented by general formula (4z-2) (TOPAS (trademark)) is more preferred. (s and t represent the number of repetitions, s is an integer of 1 or more, and t is an integer of 0 or more. R Ａ , RＢ R each independently represents hydrogen, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms. Ａ and R Ｂ may be bonded to each other to form a ring together with the carbon atoms to which they are attached.

[0114] In the above general formula (4z-1) or (4z-2), s may be 6,000 or less, and t may be 20,000 or less.

[0115] R Ａ , R Ｂ The alkyl group having 1 to 50 carbon atoms represented by the formula (I) may be linear, branched or cyclic, and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dodoriacontyl, tritriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, tetracontyl, and hentetracontyl. Examples of such groups include linear alkyl groups such as a 2-ethylhexyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, a 2-octyldodecyl group, a 2-decyltetradecyl group, a 2-dodecyltetradecyl group, a 2-dodecylhexadecyl group, a 2-tetradecylhexadecyl group, a 3-decylpentadecyl group, a 3-dodecylheptadecyl group, a 3-tetradecylnonacosyl group, a 4-decylhexadecyl group, a 4-dodecyloctadecyl group, and a 4-tetradecylicocosyl group; and cyclic alkyl groups such as a cyclopentyl group and a cyclohexyl group.

[0116] R Ａ , R ＢAs the alkyl group represented by the formula (I), an alkyl group having 1 to 34 carbon atoms is preferred, and an alkyl group having 1 to 20 carbon atoms is more preferred, in that the solubility of the conjugated polymer is further increased, and a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 3,7-dimethyloctyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, or a 2-octyldodecyl group is even more preferred, and a decyl group or a hexadecyl group is particularly preferred.

[0117] R Ａ , R ＢThe alkoxy group having 1 to 50 carbon atoms represented by the formula (I) may be either linear or branched, and examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, icosyloxy, henicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, hentriacontyloxy, and cyclohexyloxy. linear alkoxy groups such as a contyloxy group, a dodoriacontyloxy group, a tritriacontyloxy group, a tetratriacontyloxy group, a pentatriacontyloxy group, a hexatriacontyloxy group, a tetracontyloxy group, a hentetracontyloxy group, a dotetracontyloxy group, a tritetracontyloxy group, a tetratetracontyloxy group, and a pentacontyloxy group; branched alkoxy groups such as an isopropyloxy group, a 1-(2-methylpropyl)oxy group, a 2-butyloxy group, a tert-butoxy group, a 2-ethylhexyloxy group, a 3,7-dimethyloctyloxy group, a 2-decyltetradecyloxy group, a 2-dodecyltetradecyloxy group, a 2-dodecylhexadecyloxy group, and a 2-tetradecylhexadecyloxy group;Examples thereof include, from the viewpoint of further increasing the carrier mobility of an organic transistor, an alkoxy group having 1 to 34 carbon atoms is preferred, an alkoxy group having 1 to 20 carbon atoms is more preferred, and a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, nonadecyloxy group, icosyloxy group, isopropyloxy group, 1-(2-methylpropyl)oxy group, 2-butyloxy group, tert-butoxy group, 2-ethylhexyloxy group, or 3,7-dimethyloctyloxy group is even more preferred, with a methoxy group being particularly preferred;

[0118] R Ａ , R Ｂ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. Examples of such rings include a cyclopropane-1,1-diyl group, a cyclobutane-1,1-diyl group, a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, a cycloheptane-1,1-diyl group, a cyclooctane-1,1-diyl group, an indene-1,1-diyl group, and a fluorene-9,9-diyl group. In terms of further increasing the solubility of the conjugated polymer, the ring is preferably a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, an indene-1,1-diyl group, or a fluorene-9,9-diyl group, and more preferably a cyclohexane-1,1-diyl group or a fluorene-9,9-diyl group.

[0119] Among these, R Ａ , R Ｂ It is preferable that one of them is hydrogen, and it is particularly preferable that both of them are hydrogen.

[0120] Furthermore, the surface of these insulating layers may be modified with, for example, silanes such as octadecyltrichlorosilane, decyltrichlorosilane, decyltrimethoxysilane, octyltrichlorosilane, octadecyltrimethoxysilane, β-phenethyltrichlorosilane, β-phenethyltrimethoxysilane, phenyltrichlorosilane, phenyltrimethoxysilane, and phenyltriethoxysilane; or silylamines such as hexamethyldisilazane.

[0121] The insulating film (first gate and / or second gate insulating film) may contain an additive to adjust the surface energy. Examples of the additive include a silicone surfactant, a fluorine surfactant, and a hydrocarbon surfactant, and among these, a silicone surfactant is preferred.

[0122] The silicone surfactant is not particularly limited, but examples thereof include polydimethylsiloxane, polymethylphenylsiloxane, polyether-modified polydimethylsiloxane, polyetherester-modified polydimethylsiloxane, hydroxyl group-containing polyether-modified polydimethylsiloxane, acrylic group-containing polyether-modified polydimethylsiloxane, acrylic group-containing polyester-modified polydimethylsiloxane, perfluoropolyether-modified polydimethylsiloxane, perfluoropolyester-modified polydimethylsiloxane, polyether-modified polymethylphenylsiloxane, polyetherester-modified polymethylphenylsiloxane, hydroxyl group-containing polyether-modified polymethylphenylsiloxane, acrylic group-containing polyether-modified polymethylphenylsiloxane, acrylic group-containing polyester-modified polymethylphenylsiloxane, perfluoropolyether-modified polymethylphenylsiloxane, perfluoropolyester-modified polymethylphenylsiloxane, and silicone-modified acrylic compounds, of which polydimethylsiloxane and polymethylphenylsiloxane are preferred, and polymethylphenylsiloxane is more preferred.

[0123] Examples of fluorine-based surfactants include Surflon S-111, S-112, S-113, S-121, S-131, S-132, S-141, and S-145 (all manufactured by Asahi Glass Co., Ltd.); Fullard FC-93, FC-95, FC-98, FC-129, FC-135, FC-170C, FC-430, FC-431, and FC-4430 (all manufactured by Sumitomo 3M Limited); Megafac F-470, F-1405, and F-474 (all manufactured by Dainippon Ink and Chemicals, Inc.); Zonyl FS-300, FSN, FSN-100, and FSO (all manufactured by DuPont); and Eftop EF-351, EF-352, EF-801, and EF-802 (all manufactured by Jemco). Among these, Zonyl FS-300, FSN, FSN-100, and FSO (all manufactured by DuPont) are particularly suitable because of their excellent reliability and improved color development.

[0124] Examples of silicone surfactants include modified silicones KF-351A, KF-353A, KF354L, KF355A, KF-615A, KF-640, KF-642, KF-643, and KF-6011 (all manufactured by Shin-Etsu Chemical Co., Ltd.); and silicones FZ-77, FZ-2104, FZ-2105, and L-7604 (all manufactured by Dow Corning Toray Co., Ltd.). Among these, KF-355A, KF-640, KF-642, and KF-643 (all manufactured by Shin-Etsu Kogyo Co., Ltd.) are particularly preferred because of their excellent reliability and improved color development.

[0125] (Organic Semiconductor Film) The organic semiconductor film used in the organic transistor according to one embodiment of the present invention contains a conjugated polymer with a structural unit represented by the following general formula (2) and a structural unit represented by the following general formula (3). (In the formula, A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (wherein X represents a divalent heteroaromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms).

[0126] R １ , R ２ , R ３ , R ４ , R ５ and R ６The alkyl group having 1 to 50 carbon atoms represented by the formula (I) may be linear, branched or cyclic, and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dodoriacontyl, tritriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, tetracontyl, and hentetracontyl. Examples of such groups include linear alkyl groups such as a 2-ethylhexyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, a 2-octyldodecyl group, a 2-decyltetradecyl group, a 2-dodecyltetradecyl group, a 2-dodecylhexadecyl group, a 2-tetradecylhexadecyl group, a 3-decylpentadecyl group, a 3-dodecylheptadecyl group, a 3-tetradecylnonacosyl group, a 4-decylhexadecyl group, a 4-dodecyloctadecyl group, and a 4-tetradecylicocosyl group; and cyclic alkyl groups such as a cyclopentyl group and a cyclohexyl group.

[0127] R １ , R ２ , R ３ and R ４As the alkyl group represented by the formula (I), an alkyl group having 1 to 34 carbon atoms is preferred, and an alkyl group having 1 to 20 carbon atoms is more preferred, in that the solubility of the conjugated polymer is further increased, and a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 3,7-dimethyloctyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, or a 2-octyldodecyl group is even more preferred, and a decyl group or a hexadecyl group is particularly preferred.

[0128] R １ and R ２ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. Examples of such rings include a cyclopropane-1,1-diyl group, a cyclobutane-1,1-diyl group, a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, a cycloheptane-1,1-diyl group, a cyclooctane-1,1-diyl group, an indene-1,1-diyl group, and a fluorene-9,9-diyl group. In terms of further increasing the solubility of the conjugated polymer, the ring is preferably a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, an indene-1,1-diyl group, or a fluorene-9,9-diyl group, and more preferably a cyclohexane-1,1-diyl group or a fluorene-9,9-diyl group.

[0129] R ３ and R ４may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. Examples of such rings include a cyclopropane-1,1-diyl group, a cyclobutane-1,1-diyl group, a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, a cycloheptane-1,1-diyl group, a cyclooctane-1,1-diyl group, an indene-1,1-diyl group, and a fluorene-9,9-diyl group. In terms of further increasing the solubility of the conjugated polymer, the ring is preferably a cyclopentane-1,1-diyl group, a cyclohexane-1,1-diyl group, an indene-1,1-diyl group, or a fluorene-9,9-diyl group, and more preferably a cyclohexane-1,1-diyl group or a fluorene-9,9-diyl group.

[0130] R ５ and R ６ is preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 34 carbon atoms, more preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 20 carbon atoms, from the viewpoint of increasing the carrier mobility of an organic transistor, and even more preferably a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 3,7-dimethyloctyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, or a 2-octyldodecyl group, from the viewpoint of increasing the carrier mobility of an organic transistor. ５ and R ６ is particularly preferably a hydrogen atom.

[0131] Examples of the monovalent aromatic ring linking group represented by A and B include the following structures.

[0132] J １ and J ２ Each independently represents a chalcogen atom. １ and J ２As the chalcogen atom represented by the formula (I), an oxygen atom, a sulfur atom, or a selenium atom is preferable, an oxygen atom or a sulfur atom is more preferable, and a sulfur atom is even more preferable, in that the carrier mobility of the compound and the conjugated polymer of this embodiment is increased.

[0133] As the monovalent aromatic ring linking group represented by A and B, one or both of A and B are preferably linking groups represented by general formulas (4-1) to (4-8), more preferably linking groups represented by general formulas (4-1) to (4-2), and particularly preferably linking groups represented by general formula (4-1), in terms of increasing the carrier mobility of an organic transistor. In this case, A and B may be the same or different. (J １ and J ２ each independently represents a chalcogen atom.)

[0134] The optionally substituted alkyl group having 1 to 50 carbon atoms in A and B may be linear, branched, or cyclic, and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, and onacosyl. Straight-chain alkyl groups such as kutacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dodoriacontyl group, tritriacontyl group, tetratriacontyl group, pentatriacontyl group, hexatriacontyl group, tetracontyl group, hentetracontyl group, dotetracontyl group, tritetracontyl group, tetratetracontyl group, and pentacontyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylhexyl group, 3,7-dimethyloctyl group, 2-hexyloctyl group, 2-hexyldecyl group, Examples of suitable alkyl groups include branched alkyl groups such as octyldodecyl, 2-decyltetradecyl, 2-dodecyltetradecyl, 2-dodecylhexadecyl, 2-tetradecylhexadecyl, 3-decylpentadecyl, 3-dodecylheptadecyl, 3-tetradecylnonacosyl, 4-decylhexadecyl, 4-dodecyloctadecyl, and 4-tetradecylicosyl; and cyclic alkyl groups such as cyclopentyl and cyclohexyl. Of these, alkyl groups having 1 to 34 carbon atoms are preferred in that they further increase the solubility of the conjugated polymer. More preferred are alkyl groups having 1 to 20 carbon atoms, and even more preferred are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, 2-ethylhexyl, 3,7-dimethyloctyl, 2-hexyloctyl, 2-hexyldecyl, and 2-octyldodecyl groups, with decyl and hexadecyl groups being particularly preferred.

[0135] The optionally substituted alkoxy group having 1 to 50 carbon atoms in A and B may be either linear or branched, and examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, icosyloxy, henicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, and triacontyloxy groups. linear alkoxy groups such as hentriacontyloxy group, dodoriacontyloxy group, tritriacontyloxy group, tetratriacontyloxy group, pentatriacontyloxy group, hexatriacontyloxy group, tetracontyloxy group, hentriacontyloxy group, dotetracontyloxy group, tritetracontyloxy group, tetratetracontyloxy group, and pentacontyloxy group; branched alkoxy groups such as isopropyloxy group, 1-(2-methylpropyl)oxy group, 2-butyloxy group, tert-butoxy group, 2-ethylhexyloxy group, 3,7-dimethyloctyloxy group, 2-decyltetradecyloxy group, 2-dodecyltetradecyloxy group, 2-dodecylhexadecyloxy group, and 2-tetradecylhexadecyloxy group;Examples thereof include, from the viewpoint of further increasing the carrier mobility of an organic transistor, an alkoxy group having 1 to 34 carbon atoms is preferred, an alkoxy group having 1 to 20 carbon atoms is more preferred, and a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, nonadecyloxy group, icosyloxy group, isopropyloxy group, 1-(2-methylpropyl)oxy group, 2-butyloxy group, tert-butoxy group, 2-ethylhexyloxy group, or 3,7-dimethyloctyloxy group is even more preferred, with a methoxy group being particularly preferred;

[0136] As the structural unit represented by the general formula (2), a structural unit represented by the following general formula (2-1) is preferred from the viewpoint of high carrier mobility. (R １ ~R ４ represents the same meaning as above.)

[0137] As the structural unit represented by general formula (2), the following structural units can be exemplified in that they improve the film-forming properties of the conjugated polymer and the carrier mobility of the organic transistor, but the present invention is not limited to these. In the formula, n may be the same or different and represent a natural number from 1 to 50. x may be the same or different and represent a natural number from 2 to 24. y may be the same or different and represent a natural number from 1 to 24. z may be the same or different and represent a natural number from 1 to 20. Specific examples of structural units included in these are also shown below. In the above formula, C ｎ H ２ｎ＋１ , C ｘ H ２ｘ＋１ and C ｙ H ２ｙ＋１ represents a straight-chain alkyl group.

[0138] In terms of increasing the film-forming properties of the conjugated polymer and the carrier mobility of the organic transistor, the structural unit represented by general formula (2) is preferably any of the structural units represented by general formula (1-1), general formula (1-2), general formula (1-1-n6) to general formula (1-1-n20), or general formula (1-2-n6) to general formula (1-2-n20), more preferably any of the structural units represented by general formula (1-1) or general formula (1-1-n6) to general formula (1-1-n20), still more preferably any of the structural units represented by general formula (1-1-n10) to general formula (1-1-n18), and particularly preferably a structural unit represented by general formula (1-1-n16).

[0139] Examples of X include divalent heteroaromatic ring linking groups which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms, and specific examples thereof include divalent heteroaromatic ring linking groups selected from the group consisting of linking groups represented by the following general formulas (4) to (23): (In the formula, R １ , R ２ , R ３ , R４ , R ５ , R ６ , J １ and J ２ represents the same meaning as above. １ and A ２ each independently represents a chalcogen atom. ３ each independently represents a chalcogen atom, C(R １０ ) ２ , C(H)(R １０ ), Si(R １０ ) ２ or NR １０ Represents. A ４ are each independently a chalcogen atom or NR １０ Represents R ７ represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. ７ may be the same or different. ８ represents a hydrogen atom or an alkyl group having 1 to 50 carbon atoms. ８ may be the same or different. ９ represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. ９ may be the same or different. １０ represents an alkyl group having 1 to 50 carbon atoms. １０ may be the same or different. １１ represents an alkyl group having 1 to 50 carbon atoms or a thioalkyl group having 1 to 50 carbon atoms. １２ represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms. m represents 1 to 3. p and q each independently represent 0 or 1.

[0140] In terms of increasing the film formability of the conjugated polymer and the carrier mobility of the organic transistor, the structural unit represented by general formula (3) is preferably a structural unit represented by general formula (4) to general formula (14) or general formula (20), more preferably a structural unit represented by general formula (5) to general formula (11) or general formula (20), and particularly preferably a structural unit represented by general formula (6).

[0141] R ７ , R ８ , R９ , R １０ , R １１ and R １２ The alkyl group having 1 to 50 carbon atoms represented by the formula (I) may be either linear or branched, and examples thereof include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dodoriacontyl, tritriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, tetra ... Examples of such alkyl groups include linear alkyl groups such as ethyl, hentetracontyl, dotetracontyl, tritetracontyl, tetratetracontyl, and pentacontyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylhexyl, 3,7-dimethyloctyl, 2-hexyloctyl, 2-hexyldecyl, 2-octyldodecyl, 2-decyltetradecyl, 2-dodecyltetradecyl, 2-dodecylhexadecyl, 2-tetradecylhexadecyl, 3-decylpentadecyl, 3-dodecylheptadecyl, 3-tetradecylnonacosyl, 4-decylhexadecyl, 4-dodecyloctadecyl, and 4-tetradecylicosyl groups.

[0142] R ７ , R ８ , R ９ , R １０ , R １１ and R １２The alkoxy group having 1 to 50 carbon atoms represented by the formula (I) may be either linear or branched, and examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, icosyloxy, henicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, hentriacontyloxy, and cyclohexyloxy. linear alkoxy groups such as a contyloxy group, a dodoriacontyloxy group, a tritriacontyloxy group, a tetratriacontyloxy group, a pentatriacontyloxy group, a hexatriacontyloxy group, a tetracontyloxy group, a hentetracontyloxy group, a dotetracontyloxy group, a tritetracontyloxy group, a tetratetracontyloxy group, and a pentacontyloxy group; branched alkoxy groups such as an isopropyloxy group, a 1-(2-methylpropyl)oxy group, a 2-butyloxy group, a tert-butoxy group, a 2-ethylhexyloxy group, a 3,7-dimethyloctyloxy group, a 2-decyltetradecyloxy group, a 2-dodecyltetradecyloxy group, a 2-dodecylhexadecyloxy group, and a 2-tetradecylhexadecyloxy group;Examples thereof include, from the viewpoint of further increasing the carrier mobility of an organic transistor, an alkoxy group having 1 to 34 carbon atoms is preferred, an alkoxy group having 1 to 20 carbon atoms is more preferred, and a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, nonadecyloxy group, icosyloxy group, isopropyloxy group, 1-(2-methylpropyl)oxy group, 2-butyloxy group, tert-butoxy group, 2-ethylhexyloxy group, or 3,7-dimethyloctyloxy group is even more preferred, with a methoxy group being particularly preferred;

[0143] R ７ is preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 34 carbon atoms, more preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 20 carbon atoms, in that the carrier mobility of the organic transistor becomes higher, and is preferably a hydrogen atom, a fluorine atom, or a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 2-methylheptyl group, a 2-propylhexyl group, a 2-ethylheptyl group, a A 2-methyloctyl group, a 2-butylhexyl group, a 2-ethyloctyl group, a 2-methylnonyl group, a 2-butylheptyl group, a 2-propyloctyl group, a 2-ethylnonyl group, a 2-pentylheptyl group, a 2-butyloctyl group, a 2-propylnonyl group, a 2-pentyloctyl group, a 2-butylnonyl group, a 2-methyldecyl group, a 2-hexyloctyl group, a 2-pentylnonyl group, a 2-hexylnonyl group, a 2-hexyldecyl group, a 2-heptylnonyl group, or a 2-octyldodecyl group is more preferred, a hydrogen atom, a fluorine atom, a methyl group, an octyl group, or a 2-octyldodecyl group is particularly preferred, and a hydrogen atom is particularly preferred.

[0144] R ８is preferably a hydrogen atom or an alkyl group having 1 to 34 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, in that the carrier mobility of the organic transistor becomes higher, and is preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 2-methylheptyl group, a 2-propylhexyl group, a 2-ethylheptyl group, a 2-methyl More preferred are octyl, 2-butylhexyl, 2-ethyloctyl, 2-methylnonyl, 2-butylheptyl, 2-propyloctyl, 2-ethylnonyl, 2-pentylheptyl, 2-butyloctyl, 2-propylnonyl, 2-pentyloctyl, 2-butylnonyl, 2-methyldecyl, 2-hexyloctyl, 2-pentylnonyl, 2-hexylnonyl, 2-hexyldecyl, 2-heptylnonyl, and 2-octyldodecyl groups, and particularly preferred are a hydrogen atom, a methyl group, an octyl group, and a 2-octyldodecyl group, with a hydrogen atom being particularly preferred.

[0145] R ９is preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 34 carbon atoms, more preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 20 carbon atoms, in that the carrier mobility of the organic transistor becomes higher, and is preferably a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 2-methylheptyl group, a 2-propylhexyl group, a 2-ethylhexyl group, a A 2-hexyl group, a 2-hexylnonyl group, a 2-hexyldecyl group, a 2-heptylnonyl group, a 2-octylheptyl group, a 2-methyloctyl group, a 2-butylhexyl group, a 2-ethyloctyl group, a 2-methylnonyl group, a 2-butylheptyl group, a 2-propyloctyl group, a 2-ethylnonyl group, a 2-pentylheptyl group, a 2-butyloctyl group, a 2-propylnonyl group, a 2-pentyloctyl group, a 2-butylnonyl group, a 2-methyldecyl group, a 2-hexyloctyl group, a 2-pentylnonyl group, a 2-hexylnonyl group, a 2-hexyldecyl group, a 2-heptylnonyl group, or a 2-octyldodecyl group is more preferred, a hydrogen atom, a fluorine atom, a methyl group, or a hexyl group is particularly preferred, and a hydrogen atom is particularly preferred.

[0146] R １０is preferably an alkyl group having 1 to 34 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, in that the carrier mobility of the organic transistor becomes higher, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 2-methylheptyl group, a 2-propylhexyl group, and a 2-ethylheptyl group. More preferred are a 2-methyloctyl group, a 2-butylhexyl group, a 2-ethyloctyl group, a 2-methylnonyl group, a 2-butylheptyl group, a 2-propyloctyl group, a 2-ethylnonyl group, a 2-pentylheptyl group, a 2-butyloctyl group, a 2-propylnonyl group, a 2-pentyloctyl group, a 2-butylnonyl group, a 2-methyldecyl group, a 2-hexyloctyl group, a 2-pentylnonyl group, a 2-hexylnonyl group, a 2-hexyldecyl group, a 2-heptylnonyl group, or a 2-octyldodecyl group, and particularly preferred is a methyl group or an octyl group.

[0147] R １１As the alkyl group represented by the formula (I), an alkyl group having 1 to 34 carbon atoms is preferred, and an alkyl group having 1 to 20 carbon atoms is more preferred, in terms of increasing the carrier mobility of the organic transistor, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a 2-ethylhexyl group, a 2-methylheptyl group, a 2-propylhexyl group, a 2-ethyl ...

[0044] More preferred are butyl, 2-methyloctyl, 2-butylhexyl, 2-ethyloctyl, 2-methylnonyl, 2-butylheptyl, 2-propyloctyl, 2-ethylnonyl, 2-pentylheptyl, 2-butyloctyl, 2-propylnonyl, 2-pentyloctyl, 2-butylnonyl, 2-methyldecyl, 2-hexyloctyl, 2-pentylnonyl, 2-hexylnonyl, 2-hexyldecyl, 2-heptylnonyl, and 2-octyldodecyl groups, and particularly preferred are methyl, propyl, and hexyl groups.

[0148] R １１Examples of the thioalkyl group having 1 to 50 carbon atoms represented by the formula (I) include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, a undecylthio group, a dodecylthio group, a tridecylthio group, a tetradecylthio group, a pentadecylthio group, a hexadecylthio group, a heptadecylthio group, an octadecylthio group, a nonadecylthio group, an icosylthio group, a 2-ethylhexylthio group, a 2-methylheptylthio group, a 2-propylhexylthio group, a 2-ethylheptylthio group, a 2-methyloct ... Examples of the alkylthio group include a 2-butylhexylthio group, a 2-ethyloctylthio group, a 2-methylnonylthio group, a 2-butylheptylthio group, a 2-propyloctylthio group, a 2-ethylnonylthio group, a 2-pentylheptylthio group, a 2-butyloctylthio group, a 2-propylnonylthio group, a 2-pentyloctylthio group, a 2-butylnonylthio group, a 2-methyldecylthio group, a 2-hexyloctylthio group, a 2-pentylnonylthio group, a 2-hexylnonylthio group, a 2-hexyldecylthio group, a 2-heptylnonylthio group, and a 2-octyldodecylthio group.In terms of increasing the carrier mobility of an organic transistor, a thioalkyl group having 1 to 34 carbon atoms is preferred, and a thioalkyl group having 1 to 20 carbon atoms is more preferred, and examples thereof include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, a tridecylthio group, a tetradecylthio group, a pentadecylthio group, a hexadecylthio group, a heptadecylthio group, an octadecylthio group, a nonadecylthio group, an icosylthio group, a 2-ethylhexylthio group, a 2-methylheptylthio group, a 2-propylhexylthio group, a 2-ethyl ... A methylthio group, a 2-methyloctylthio group, a 2-butylhexylthio group, a 2-ethyloctylthio group, a 2-methylnonylthio group, a 2-butylheptylthio group, a 2-propyloctylthio group, a 2-ethylnonylthio group, a 2-pentylheptylthio group, a 2-butyloctylthio group, a 2-propylnonylthio group, a 2-pentyloctylthio group, a 2-butylnonylthio group, a 2-methyldecylthio group, a 2-hexyloctylthio group, a 2-pentylnonylthio group, a 2-hexylnonylthio group, a 2-hexyldecylthio group, a 2-heptylnonylthio group, or a 2-octyldodecylthio group is more preferred, and a methylthio group or a propylthio group is particularly preferred.

[0149] R １１is preferably an alkyl group having 1 to 34 carbon atoms or a thioalkyl group having 1 to 34 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms or a thioalkyl group having 1 to 20 carbon atoms, in that the carrier mobility of the organic transistor becomes higher, and is preferably a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, or a nonadecyl group , icosyl group, methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, heptylthio group, octylthio group, nonylthio group, decylthio group, undecylthio group, dodecylthio group, tridecylthio group, tetradecylthio group, pentadecylthio group, hexadecylthio group, heptadecylthio group, octadecylthio group, nonadecylthio group, or icosylthio group is more preferred, and methyl group, propyl group, hexyl group, methylthio group, or propylthio group is particularly preferred.

[0150] R １２ As the alkyl group having 1 to 50 carbon atoms represented by the formula (I), an alkyl group having 1 to 34 carbon atoms is preferred, and an alkyl group having 1 to 20 carbon atoms is more preferred, from the viewpoint of further increasing the carrier mobility of an organic transistor, and a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethylhexyl group, a 3,7-dimethyloctyl group, a 2-hexyloctyl group, a 2-hexyldecyl group, or a 2-octyldodecyl group is even more preferred, and a methyl group is particularly preferred.

[0151] R １２The alkoxy group having 1 to 50 carbon atoms represented by the formula (I) may be either linear or branched, and examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, icosyloxy, henicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, hentriacontyloxy, and cyclohexane. Examples of alkoxy groups include linear alkoxy groups such as a silyl group, a dodoriacontyloxy group, a tritriacontyloxy group, a tetratriacontyloxy group, a pentatriacontyloxy group, a hexatriacontyloxy group, a tetracontyloxy group, a hentetracontyloxy group, a dotetracontyloxy group, a tritetracontyloxy group, a tetratetracontyloxy group, and a pentacontyloxy group; and branched alkoxy groups such as an isopropyloxy group, a 1-(2-methylpropyl)oxy group, a 2-butyloxy group, a tert-butoxy group, a 2-ethylhexyloxy group, a 3,7-dimethyloctyloxy group, a 2-decyltetradecyloxy group, a 2-dodecyltetradecyloxy group, a 2-dodecylhexadecyloxy group, and a 2-tetradecylhexadecyloxy group.In terms of further increasing the carrier mobility of an organic transistor, an alkoxy group having 1 to 34 carbon atoms is preferred, an alkoxy group having 1 to 20 carbon atoms is more preferred, and a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a nonadecyloxy group, an icosyloxy group, an isopropyloxy group, a 1-(2-methylpropyl)oxy group, a 2-butyloxy group, a tert-butoxy group, a 2-ethylhexyloxy group, or a 3,7-dimethyloctyloxy group is even more preferred. A methoxy group is particularly preferred.

[0152] R １２is preferably a hydrogen atom, a fluorine atom, an alkyl group having 1 to 34 carbon atoms, or an alkoxy group having 1 to 34 carbon atoms, from the viewpoint of increasing the carrier mobility of an organic transistor, more preferably a hydrogen atom, a fluorine atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, and more preferably a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a decyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, 2-ethylhexyl group, 2-methylheptyl group, 2-propylhexyl group, 2-ethylheptyl group, 2-methyloctyl group, 2-butylhexyl group, 2-ethyloctyl group, 2-methylnonyl group, 2-butylheptyl group, 2-propyloctyl group, 2-ethylnonyl group, 2-pentylheptyl group, 2-butyloctyl group, 2-propyl propylnonyl group, 2-pentyloctyl group, 2-butylnonyl group, 2-methyldecyl group, 2-hexyloctyl group, 2-pentylnonyl group, 2-hexylnonyl group, 2-hexyldecyl group, 2-heptylnonyl group, 2-octyldodecyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, A tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a nonadecyloxy group, an icosyloxy group, an isopropyloxy group, a 1-(2-methylpropyl)oxy group, a 2-butyloxy group, a tert-butoxy group, a 2-ethylhexyloxy group, or a 3,7-dimethyloctyloxy group is more preferred, and a hydrogen atom, a fluorine atom, a methyl group, or a methoxy group is particularly preferred.

[0153] A １ , A ２ , A ３ and A ４ Examples of the chalcogen atom represented by the formula (I) include an oxygen atom, a sulfur atom, and a selenium atom.

[0154] A １As the chalcogen atom represented by the formula (I), an oxygen atom, a sulfur atom, or a selenium atom is preferred, an oxygen atom or a sulfur atom is more preferred, and a sulfur atom is even more preferred, in terms of increasing the carrier mobility of an organic transistor.

[0155] A ２ As the chalcogen atom represented by the formula (I), an oxygen atom, a sulfur atom, or a selenium atom is preferred, an oxygen atom or a sulfur atom is more preferred, and a sulfur atom is even more preferred, in terms of increasing the carrier mobility of an organic transistor.

[0156] A ３ As the organic EL element, sulfur atoms, selenium atoms, and C(R １０ ) ２ , C(H)(R １０ ), Si(R １０ ) ２ or NR １０ is preferred, and C(R １０ ) ２ , C(H)(R １０ ), Si(R １０ ) ２ or NR １０ More preferably, C(R １０ ) ２ or C(H)(R １０ ) is more preferred.

[0157] A ４ As the cation, an oxygen atom, a sulfur atom, a selenium atom or an NR atom is preferred in that the carrier mobility of the organic transistor is increased. １０ is preferred, an oxygen atom or a sulfur atom is more preferred, and a sulfur atom is even more preferred.

[0158] m represents 1 to 3, and is preferably 2 in that it improves the film-forming properties of the conjugated polymer and the carrier mobility of the organic transistor.

[0159] p and q each represent 0 or 1, and are preferably 0 in that the film-forming properties of the conjugated polymer and the carrier mobility of the organic transistor are improved.

[0160] As the structural unit represented by general formula (3), the following structural units can be exemplified in terms of increasing the solubility of the conjugated polymer, but the present invention is not limited to these. In the formula, k may be the same or different and represent a natural number from 1 to 50. x may be the same or different and represent a natural number from 2 to 24. y may be the same or different and represent a natural number from 1 to 24. Specific examples of structural units included in these are also shown below. In the above formula, C ｋ H ２ｋ＋１ , C ｘ H ２ｘ＋１ and C ｙ H ２ｙ＋１ represents a straight-chain alkyl group.

[0161] As the structural unit represented by general formula (3), in terms of increasing the film-forming property of the conjugated polymer and the carrier mobility of the organic transistor, formula (11-1-1) to formula (11-1-5), formula (11-2-1) to formula (11-2-5), formula (11-3-1) to formula (11-3-3), formula (11-3-7), formula (11-4-1) to formula (11-4-9), formula (11-5-1) to formula (11-5-7), formula (11-5-11), formula (11-5-12), formula (11-6-1) to formula (11-6-6), formula (11-7-1), formula (11-7-2), formula (11-8-1), formula (11-8-2), Formula (11-9-1) to Formula (11-9-4), Formula (11-1-5-k1) to Formula (11-1-5-k6), Formula (11-2-4-k1) to Formula (1 1-2-4-k6), formula (11-2-5-k1) to formula (11-2-5-k6), formula (11-3-3-k1) to formula (11-3-3-k6), Formula (11-3-7-k1) ~ Formula (11-3-7-k8), Formula (11-4-4-k1) ~ Formula (11-4-4-k6), Formula (11-4-5-k 1) ~ Formula (11-4-5-k6), Formula (11-4-6-k1) ~ Formula (11-4-6-k6), Formula (11-4-7-k1) ~ Formula (11-4-7) -k6), formula (11-4-8-k1) to formula (11-4-8-k6), formula (11-4-9-k1) to formula (11-4-9-k6), formula (11- 5-3-k1) ~ Formula (11-5-3-k6), Formula (11-5-4-k1) ~ Formula (11-5-4-k6), Formula (11-5-5-k1) ~ Formula ( 11-5-5-k6), formula (11-5-6-k1) to formula (11-5-6-k6), formula (11-5-7-k1) to formula (11-5-7-k6) , Formula (11-5-11-k1) ~ Formula (11-5-11-k10), Formula (11-5-12-k1) ~ Formula (11-5-12-k10), Formula (11 -6-6-k1), formula (11-9-1-k1) to formula (11-9-1-k10), formula (11-9-2-x4-y2) to formula (11-9-2-x10-y8), formula (11-9-3-k1), formula (11-9-3-k10), formula (11-9-4-x4-y2) or formula (11-9-4-x10-y8) are preferred structural units represented by formula (11-1-2), formula (11-1-4), formula (11-2-1), formula (11-2-3), formula (11-2-5), formula (11-3-1), formula (11-3-2), formula (11-3-7), formula (11-4-4), formula (11-4-5),Formula (11-4-7), Formula (11-4-8), Formula (11-4-9), Formula (11-5-3), Formula (11-5-4), Formula (11-5-6), Formula ( 11-5-7), formula (11-5-11), formula (11-5-12), formula (11-6-3), formula (11-6-4), formula (11-7-2), formula ( 11-8-2), formula (11-9-1), (11-9-2), formula (11-2-5-k1) to formula (11-2-5-k6), formula (11-3-3- k1) ~ Formula (11-3-3-k6), Formula (11-3-7-k1) ~ Formula (11-3-7-k8), Formula (11-4-4-k1) ~ Formula (11-4- 4-k6), formula (11-4-5-k1) to formula (11-4-5-k6), formula (11-4-7-k1) to formula (11-4-7-k6), formula (11 -4-8-k1) ~ Formula (11-4-8-k6), Formula (11-4-9-k1) ~ Formula (11-4-9-k6), Formula (11-5-3-k1) ~ Formula ( 11-5-3-k6), formula (11-5-4-k1) to formula (11-5-4-k6), formula (11-5-6-k1) to formula (11-5-6-k6) , formula (11-5-7-k1) to formula (11-5-7-k6), formula (11-5-11-k1) to formula (11-5-11-k10), formula (11-5- 12-k1) to formula (11-5-12-k10), formula (11-9-1-k1) to formula (11-9-1-k10) or formula (11-9-2-x4-y2) to formula (11-9-2-x10-y8) are more preferred structural units, and the structural units are represented by formula (11-1-2), formula (11-2-1), formula (11-3-1), formula (11-3-7), formula (11-4-4), formula (11-4-7), formula (11-4-8), formula (11-4-9), formula (11-5-3), formula (11-9-1), formula (11-9-2), formula (11-3-3-k1) to formula (11-3-3-k6), formula (11-3-7- k1) to formula (11-3-7-k8), formula (11-4-4-k1) to formula (11-4-4-k6), formula (11-4-7-k1) to formula (11-4-7-k6), formula (11-4-8-k1) to formula (11-4-8-k6), formula (11-4-9-k1) to formula (11-4-9-k6), formula (11-5-3-k1) to formula (11-5-3-k6), formula (11-9-1-k1) to formula (11-9-1-k10) or formula (11-9-2-x4-y2) to formula (11-9-2-x10-y8) are more preferred structural units, such as formula (11-1-2), formula (11-2-1),Any structural unit represented by the formula (11-3-1), formula (11-3-3-k4), formula (11-3-3-k6), formula (11-3-7-k8), formula (11-4-4-k1), formula (11-4-7-k1), formula (11-4-8-k1), formula (11-4-8-k3), formula (11-4-9-k1), formula (11-5-3-k1), formula (11-9-1-k1), formula (11-9-1-k8) or formula (11-9-2-x10-y8) is particularly preferred.

[0162] The conjugated polymer is not particularly limited in the order of the structural units as long as it contains a structural unit represented by general formula (2) and a structural unit represented by general formula (3), and examples of such copolymerization modes include alternating, random, block, and gradient copolymerization. In terms of improving the film-forming ability and mobility of the conjugated polymer, a conjugated polymer having a structure in which the structural unit represented by general formula (2) and the structural unit represented by general formula (3) are alternately repeated is preferred, and it is more preferred that this structure is represented by general formula (24), and that X in general formula (24) is a linking group selected from the group consisting of the following general formulas (3-1) to (3-3). It is even more preferred that the conjugated polymer is composed of structural units represented by general formula (24), and that X is a linking group represented by the following general formulas (3-1) to (3-3), and that at least one of A and B is a linking group represented by general formulas (4-1) to (4-8). Furthermore, it is particularly preferable that the conjugated polymer is composed of a structural unit represented by general formula (24), in which A and B in general formula (24) are linking groups represented by general formula (4-1), and X is a linking group selected from the group consisting of general formulas (3-1) to (3-3). (In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , J １ , J ２ and X have the same meaning as above. (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and R ｈeach independently represents hydrogen, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms.

[0163] R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and R ｈ Examples of the alkyl group having 1 to 50 carbon atoms and the alkoxy group having 1 to 50 carbon atoms in A and B in general formula (2) include the same alkyl group having 1 to 50 carbon atoms and alkoxy group having 1 to 50 carbon atoms as A and B in general formula (2).

[0164] R ａ , R ｂ , R ｅ , R ｆ , R ｇ and R ｈ is preferably hydrogen or an alkyl group having 1 to 50 carbon atoms, and more preferably hydrogen.

[0165] R ｃ and R ｄ As the alkyl group, hydrogen or an alkyl group having 1 to 50 carbon atoms is preferred, hydrogen or a methyl group is more preferred, and a methyl group is particularly preferred.

[0166] Examples of the structural unit represented by general formula (24) include structural units represented by the following, but the present invention is not limited to these. In the formula, n may be the same or different and represent a natural number from 1 to 50. k may be the same or different and represent a natural number from 1 to 50. x may be the same or different and represent a natural number from 2 to 24. y may be the same or different and represent a natural number from 1 to 24. z may be the same or different and represent a natural number from 1 to 20. Specific examples of structural units included in these are also shown below. In the above formula, C ｎ H ２ｎ＋１ , C ｋ H ２ｋ＋１ , C ｘ H ２ｘ＋１ and C ｙ H ２ｙ＋１ represents a straight-chain alkyl group.

[0167] The film-forming property of the co-functional polymer and the mobility of the organic polymer are high and the point is high, the general formula (24) and the table structure unit position, formula (3-1) -2), formula (3-1-4), formula (3-1-6), formula (3-1-8), formula (3-1-10), formula (3-1-11), formula (3-1-13), formula (3-1-17), formula (3-1-18), formula (3-1-20), formula (3-1-21), formula (3-1-24), formula (3-1-25), formula (3-1-27), formula (3-1-28), formula (3-1-32), formula (3-1-33), formula (3-1-34), formula (3-1-35), formula (3-1-2-n6) to formula (3-1-2-n19), formula (3-1-4-n6), formula (3-1-4-n16), formula (3-1-6-n6) to formula (3-1-6-n19), formula (3-1-8-n6), formula (3-1-8-n16), formula (3-1-10-n6), formula (3-1-10-n16), formula ( 3-1-11-n6)、Funct(3-1-11-n16)、Funct(3-1-12-n6-k1)、Funct(3-1-12-n16-k1)、Funct(3-1-12-n16-k4)、Funct(3-1-12-n16-k4)、Funct(3-1-12-n1-k6)、Funct(3-1-12-n16-k6) 、Formula (3-1-13-n6-k1)~Formula (3-1-13-n16-k1)、Formula (3-1-13-n6-k8)~Formula (3-1-13-n16-k8)、Formula (3-1-17-n6-k1)~Formula (3-1-17-n16-k1)、Formula (3-1-17-n6-k6)~Formula (3-1-17 -n16-k6), formula (3-1-18-n6-k1), formula (3-1-18-n16-k1), formula (3-1-18-n6-k6), formula (3-1-18-n16-k6), formula (3-1-20-n6-k1) ~ formula (3-1-20-n16-k1), formula (3-1-20-n6-k3) ~ Formula (3-1-20-n16-k3), formula (3-1-20-n6-k6) ~ formula (3-1-20-n16-k6), formula (3-1-21-n6-k1) ~ formula (3-1-21-n16-k1), formula (3-1-21-n6-k3) ~ formula (3-1-21-n16-k3), formula (3-1-21 -n6-k6) ~ formula (3-1-21-n16-k6), formula (3-1-24-n6-k1) ~ formula (3-1-24-n16-k1), formula (3-1-24-n6-k6) ~ formula (3-1-24-n16-k6), formula (3-1-25-n6-k1), formula (3-1-25-n16-k1),Any of the structural units represented by formula (3-1-25-n6-k6), formula (3-1-25-n16-k6), formula (3-1-27-n6-k1), formula (3-1-27-n16-k1), formula (3-1-27-n6-k6), formula (3-1-27-n16-k6), formula (3-1-28-n6-k1), formula (3-1-28-n16-k1), formula (3-1-28-n6-k6), formula (3-1-28-n16-k6), formula (3-1-32-n6-k1), formula (3-1-32-n16-k1), formula (3-1-32-n6-k6), formula (3-1-32-n16-k6), formula (3-1-33-n6-k1), formula (3-1-33-n16-k1), formula (3-1-33-n6-k6), formula (3-1-33-n16-k6), formula (3-1-34-n6-k1), formula (3-1-34-n16-k1), formula (3-1-34-n6-k6), formula (3-1-34-n16-k6), formula (3-1-34-n6-k10), formula (3-1-34-n16-k10), formula (3-2-3), formula (3-2-4), formula (3-2-9), formula (3-2-12), formula (3-2-14), formula (3-2-15), formula (3-2-14-n6-k1) to formula (3-2-14-n16-k1), formula (3-2-14-n6-k8) to formula (3-2-14-n16-k8), formula (3-2-15-n6-x4-y2), formula (3-2-15-n16-x4-y2), formula (3-2-15-n6-x8-y6), formula (3-2-15-n16-x8-y6), formula (3-2-15-n6-x10-y8), formula (3-2-15-n16-x10-y8), formula (4-1-2), formula (4-1-4), formula (4-1-6), formula (4-1-8), formula (4-1-10), formula (4-1-11), formula (4-1-13), formula (4-1-17), formula (4-1-18), formula (4-1-20), formula (4-1-21), formula (4-1-24), formula (4-1-25), formula (4-1-27), formula (4-1-28), formula (4-1-34), formula (4-2-3), formula (4-2-4), formula (4-2-9), formula (4-2-12), formula (4-2-14) or formula (4-2-15) is preferred, and formula (3-1-2), formula (3-1-6), formula (3-1-10), formula (3-1-13), formula (3-1-17), formula (3-1-20), formula (3-1-21), formula (3-1-24), formula (3-1-25), formula (3-1-2-n6) to formula (3-1-2-n19),Any of the structural units represented by Formula (3-1-6-n6) to Formula (3-1-6-n19), Formula (3-1-10-n6), Formula (3-1-10-n16), Formula (3-1-12-n6-k1), Formula (3-1-12-n16-k1), Formula (3-1-12-n16-k4), Formula (3-1-12-n16-k4), Formula (3-1-12-n1-k6), Formula (3-1-12-n16-k6), Formula (3-1-13-n6-k1) to Formula (3-1-13-n16-k1), Formula (3-1-13-n6-k8) to Formula (3-1-13-n16-k8), Formula (3-1-17-n6-k1) to Formula (3-1-17-n16-k1), Formula (3-1-17-n6-k6) to Formula (3-1-17-n16-k6), Formula (3-1-20-n6-k1) to Formula (3-1-20-n16-k1), Formula (3-1-20-n6-k3) to Formula (3-1-20-n16-k3), Formula (3-1-20-n6-k6) to Formula (3-1-20-n16-k6), Formula (3-1-21-n6-k1) to Formula (3-1-21-n16-k1), Formula (3-1-21-n6-k3) to Formula (3-1-21-n16-k3), Formula (3-1-21-n6-k6) to Formula (3-1-21-n16-k6), Formula (3-1-24-n6-k1) to Formula (3-1-24-n16-k1), Formula (3-1-24-n6-k6) to Formula (3-1-24-n16-k6), Formula (3-1-35-n6-k1), Formula (3-1-35-n8-k1), Formula (3-1-35-n10-k1), Formula (3-1-35-n12-k1), Formula (3-1-35-n14-k1), Formula (3-1-35-n16-k1), Formula (3-2-14), Formula (3-2-15), Formula (3-2-14-n6-k1) to Formula (3-2-14-n16-k1), Formula (3-2-14-n6-k8) to Formula (3-2-14-n16-k8), Formula (3-2-15-n6-x4-y2), Formula (3-2-15-n16-x4-y2), Formula (3-2-15-n6-x8-y6), Formula (3-2-15-n16-x8-y6), Formula (3-2-15-n6-x10-y8) or Formula (3-2-15-n16-x10-y8) is more preferred, and Formula (3-1-2-n6) to Formula (3-1-2-n19), Formula (3-1-6-n6) to Formula (3-1-6-n19), Formula (3-1-10-n6), Formula (3-1-10-n):Formula (3-1-12-n16-k4), Formula (3-1-12-n16-k6), Formula (3-1-12-n16-k6), Formula (3-1-13-n6-k8) ~ Formula (3-1-13-n16-k8), Formula (3-1-17-n6-k1) ~ Formula (3- 1-17-n16-k1), formula (3-1-20-n6-k1) to formula (3-1-20-n16-k1), formula (3-1-21-n6-k1) to formula (3-1-21-n16-k1), formula (3-1-21-n6-k3) to formula (3-1-21- n16-k3), formula (3-1-24-n6-k1) to formula (3-1-24-n16-k1), formula (3-1-35-n6-k1), formula (3-1-35-n8-k1), formula (3-1-35-n10-k1), formula (3-1-35-n12-k) 1), Formula (3-1-35-n14-k1), Formula (3-1-35-n16-k1), Formula (3-2-14-n6-k1) ~ Formula (3-2-14-n16-k1), Formula (3-2-14-n6-k8) ~ Formula (3-2-14-n16-k8), Formula Any structural unit represented by (3-2-15-n6-x10-y8) or formula (3-2-15-n16-x10-y8) is more preferred, and the structural units represented by formula (3-1-2-n9) to formula (3-1-2-n12), formula (3-1-2-n16), formula (3-1-6-n10), formula (3-1-6-n16), formula (3-1-6-n18), formula (3-1-10-n16), formula (3-1-13-n16-k4), formula (3-1-13-n16-k6), formula (3-1-13-n10-k8), formula (3 -1-13-n16-k8), formula (3-1-17-n10-k1), formula (3-1-17-n16-k1), formula (3-1-20-n16-k1), formula (3-1-21-n16-k1), formula (3-1-21-n16-k3), formula (3-1-24-n16-k1), formula (3-1-35-n16-k1), formula (3-2-14-n6-k1), formula (3-2-14-n6-k8) or formula (3-2-15-n16-x10-y8).

[0168] The conjugated polymer may contain structural units other than the structural unit represented by general formula (2) and the structural unit represented by general formula (3) within a range that does not impair the effects of the present invention. The total content of the structural unit represented by general formula (2) and the structural unit represented by general formula (3) in the conjugated polymer is preferably 90% by mass or more, more preferably 95% by mass or more.

[0169] The terminal structure of the conjugated polymer is not particularly limited, and examples thereof include a hydrogen atom, a boron-containing group such as a dihydroxyboryl group or a dialkoxyboryl group, a tin-containing group such as a trimethylstannyl group or a tributylstannyl group, a halogen atom such as a chlorine atom, a bromine atom or an iodine atom, and an aromatic group such as a phenyl group or a thienyl group, and the structures of both terminals may be the same or different.

[0170] The weight average molecular weight (Mw) of the conjugated polymer is preferably 3,000 to 10,000,000, more preferably 3,000 to 1,000,000, and even more preferably 3,000 to 500,000.

[0171] The molecular weight distribution (PDI) of the conjugated polymer is preferably from 1.05 to 20.0, more preferably from 1.2 to 10.0, even more preferably from 1.2 to 9.0, and particularly preferably from 1.2 to 8.0.

[0172] In the conjugated polymer, the molar ratio of the structural unit represented by general formula (2) to the structural unit represented by general formula (3) (structural unit represented by general formula (2):structural unit represented by general formula (3)) is not particularly limited, but is preferably in the range of 10:1 to 1:10, more preferably in the range of 5:1 to 1:5, even more preferably in the range of 2:1 to 1:2, particularly preferably in the range of 1.2:1 to 1:1.2, and particularly preferably 1:1.

[0173] Next, a method for producing a conjugated polymer will be described. The method for producing a conjugated polymer is as follows.

[0174] The production method is a method of producing a conjugated polymer by coupling a compound (monomer) represented by the general formula (mono-hal) with a compound (monomer) represented by the general formula (mono-X-Sn) in the presence of a transition metal catalyst. (In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , J １ , J ２ , X has the same meaning as above. １－ｈａｌ and M ２－ｈａｌ each independently represents a halogen atom; M ３－Ｓｎ and M ４－Ｓｎ each independently represents a tin-containing group.

[0175] M １－ｈａｌ and M ２－ｈａｌ As the halogen atom represented by the formula (I), a chlorine atom, a bromine atom or an iodine atom is preferred, a bromine atom or an iodine atom is more preferred, and a bromine atom is even more preferred, in terms of improving the production efficiency of the conjugated polymer.

[0176] M ３－Ｓｎ , and M ４－Ｓｎ Examples of the tin-containing group represented by the formula (13) include a trialkylstannyl group, a dialkylarylstannyl group, an alkyldiarylstannyl group, and a triarylstannyl group. In terms of improving the production efficiency of conjugated polymers, a trialkylstannyl group or a triarylstannyl group is preferred, any of the groups represented by general formulas (13-1) to (13-5) is more preferred, and a group represented by general formula (13-1) is even more preferred. In this specification, Me, Et, Pr, Bu, and Ph represent a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, respectively.

[0177] The production method must be carried out in the presence of a transition metal catalyst, and examples of usable transition metal catalysts include palladium catalysts, nickel catalysts, and platinum catalysts. These transition metal catalysts can be "metals," "supported metals," "metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates, or oxides," or "complex compounds such as olefin complexes, phosphine complexes, amide complexes, amine complexes, carbene complexes, or acetylacetonate complexes." In terms of good reaction yield, the use of a palladium catalyst or nickel catalyst is preferred, and the use of a palladium catalyst is even more preferred. Furthermore, these metals, supported metals, metal salts, and complex compounds can also be used in combination with tertiary phosphorus compounds, carbene compounds, or the like.

[0178] The palladium catalyst is not particularly limited, but examples thereof include palladium metal such as palladium black and palladium sponge, and also examples thereof include palladium metal supported on palladium / alumina, palladium / carbon, palladium / silica, palladium / Y-type zeolite, and the like. Further, metal salts such as palladium chloride, palladium bromide, palladium iodide, palladium acetate, palladium trifluoroacetate, and palladium nitrate, π-allylpalladium chloride dimer, palladium acetylacetonate, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, dichlorodiamminepalladium, dichlorobis(triphenylphosphine)palladium, dichlorobis(tricyclohexylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro[1,2-bis(diphenylphosphino)ethane]palladium, dichloro[1,3-bis(diphenylphosphino)propane]palladium, dichloro[1,4-bis(diphenylphosphine) Examples of palladium catalysts include [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (Pd-PEPPSI-IPent), [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (Pd-PEPPSI-IPr), and [1,3-bis(2,6-diisopropylphenyl)imidazolidine-2-ylidene](3-chloropyridyl)palladium(II) dichloride (Pd-PEPPSI-SIPr).

[0179] Among these palladium catalysts, palladium acetate, palladium acetylacetonate, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, and tetrakis(triphenylphosphine)palladium (Pd(PPh ３ ) ４ ), bis(tri-tert-butylphosphine)palladium is preferably used.

[0180] The nickel catalyst is not particularly limited, but specific examples include nickel catalysts such as nickel chloride (II), bis(triphenylphosphine)nickel (II) dichloride, bis(2,4-pentanedionato)nickel (II) hydrate, bis(1,5-cyclooctadiene)nickel (0), dichloro(1,1′-bis(diphenylphosphino)ethane)nickel, dichloro(1,1′-bis(diphenylphosphino)propane)nickel, and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]triphenylphosphinenickel (II) dichloride.

[0181] These palladium catalysts or nickel catalysts may be used alone or in combination with a tertiary phosphorus compound or a carbene compound. Examples of the tertiary phosphorus compound that can be used include triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, tri(o-tolyl)phosphine, tris(2-methoxyphenyl)phosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, and 1,3-bis(diphenylphosphino)propane. , 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, tert-butyldiphenylphosphine, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, bis(diphenylphosphino)methane, 1,4-bis(diphenylphosphino)butane, tri(2-furyl)phosphine, tris(2,5-xylyl)phosphine, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and the like can be exemplified. Examples of the carbene compound that can be used include 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, 1,3-bis(2,6-diisopropylphenyl)imidazolidine-2-ylidene, 1,3-di-tert-butylimidazol-2-ylidene, and 1,3-dimesitylimidazol-2-ylidene.

[0182] In terms of good reaction yield, it is preferable to use triphenylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, or tri(o-tolyl)phosphine as the tertiary phosphorus compound.

[0183] The molar ratio of the tertiary phosphorus compound to the transition metal catalyst (tertiary phosphorus compound:transition metal catalyst) is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:5 to 5:1 in terms of a good reaction yield.

[0184] The amount of the transition metal catalyst used is not particularly limited, but in terms of good reaction yield, it is preferably 0.001 to 50 mol % and more preferably 0.1 to 20 mol % relative to the compound represented by the general formula (mono-hal).

[0185] The production method can also use a promoter. The promoter is not particularly limited, but specific examples include monovalent or divalent copper salts such as copper fluoride, copper chloride, copper bromide, copper iodide, and copper oxide.

[0186] The production method can be carried out in a solvent. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction, and examples thereof include aliphatic hydrocarbon solvents such as hexane, heptane, decane, and tridecane; ether solvents such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, and tetralin; carbonate solvents such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ester solvents such as ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone; N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP). urea solvents such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); sulfoxide solvents such as dimethyl sulfoxide (DMSO); alcohol solvents such as methanol, ethanol, 2-propanol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; halogenated solvents such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and o-dichlorobenzene (DCB); fluorinated solvents such as bis(2,2,2-trifluoroethyl)=N,N-diisopropylphosphoramidate (PF-37) and phosphoric acid=tris(2,2,2-trifluoroethyl) (TFEP); nitromethane; water; and the like, and these may be mixed and used in any ratio.In terms of a good reaction yield, an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent, a halogenated solvent, an ether solvent, an amide solvent, a sulfoxide solvent, a fluorinated solvent, a mixed solvent of an aromatic hydrocarbon solvent and water, a mixed solvent of a halogenated solvent and water, a mixed solvent of an ether solvent and water, a mixed solvent of an aromatic hydrocarbon solvent and a sulfoxide solvent, a mixed solvent of a halogenated solvent and a sulfoxide solvent, a mixed solvent of an ether solvent and a sulfoxide solvent, a mixed solvent of an aromatic hydrocarbon solvent and a fluorinated solvent, a mixed solvent of a halogenated solvent and a fluorinated solvent, or a mixed solvent of an ether solvent and a fluorinated solvent is more preferred, and tetralin, toluene, chlorobenzene, o-DCB, or THF is even more preferred.

[0187] There is no particular limitation on the amount of solvent used, but it is preferably in the range of 0.001 to 100 mL / mg relative to the weight of the compound represented by the general formula (mono-hal).

[0188] The production method can be carried out at a temperature appropriately selected from 0°C to 240°C, and is preferably carried out at a temperature appropriately selected from 70°C to 220°C in terms of good reaction yield, and more preferably at a temperature appropriately selected from 100°C to 200°C.

[0189] The preparation method can also be carried out using a microwave reactor.

[0190] The production method is preferably carried out in an inert gas atmosphere such as argon gas or nitrogen gas, or under reduced pressure.

[0191] The reaction time varies depending on the compound used (the compound represented by the general formula (mono-hal) or the general formula (mono-X-Sn)), the solvent, and the reaction temperature, but is preferably 0.1 to 100 hours, more preferably 1 to 90 hours.

[0192] The conjugated polymer can be obtained by carrying out a normal treatment after the completion of the production method, and may be purified, if necessary, by any of the general means used by those skilled in the art for purifying polymer compounds, such as washing, precipitation, filtration, dialysis, column chromatography, preparative HPLC, or Soxhlet extraction.

[0193] For the purpose of improving the carrier mobility or solubility of the resulting conjugated polymer, an organoboron compound or an organotin compound can be added during or after the reaction to produce a conjugated polymer having a functional group such as a thienyl group or a phenyl group introduced at its terminal. The functional group may be introduced by a combination of known methods, and can be introduced, for example, according to the method disclosed in Non-Patent Document (Macromolecules, Vol. 48, pp. 6994-7006, 2015, etc.).

[0194] The compound represented by the general formula (mono-X-Sn) used in the production method may be obtained by any method, and may be produced by referring to, for example, methods described in non-patent literature (Journal of the American Chemical Society, Vol. 134, pp. 3498-3507, 2012, Nature Chem, Vol. 11, pp. 271-277, 2019, etc.). Alternatively, commercially available products may be used.

[0195] The organic semiconductor film may contain additives to adjust the surface energy. Examples of such additives include silicone surfactants, fluorine surfactants, and hydrocarbon surfactants, with silicone surfactants being preferred.

[0196] The silicone surfactant is not particularly limited, but examples thereof include polydimethylsiloxane, polymethylphenylsiloxane, polyether-modified polydimethylsiloxane, polyetherester-modified polydimethylsiloxane, hydroxyl group-containing polyether-modified polydimethylsiloxane, acrylic group-containing polyether-modified polydimethylsiloxane, acrylic group-containing polyester-modified polydimethylsiloxane, perfluoropolyether-modified polydimethylsiloxane, perfluoropolyester-modified polydimethylsiloxane, polyether-modified polymethylphenylsiloxane, polyetherester-modified polymethylphenylsiloxane, hydroxyl group-containing polyether-modified polymethylphenylsiloxane, acrylic group-containing polyether-modified polymethylphenylsiloxane, acrylic group-containing polyester-modified polymethylphenylsiloxane, perfluoropolyether-modified polymethylphenylsiloxane, perfluoropolyester-modified polymethylphenylsiloxane, and silicone-modified acrylic compounds, of which polydimethylsiloxane and polymethylphenylsiloxane are preferred, and polymethylphenylsiloxane is more preferred.

[0197] Examples of fluorine-based surfactants include Surflon S-111, S-112, S-113, S-121, S-131, S-132, S-141, and S-145 (all manufactured by Asahi Glass Co., Ltd.); Fullard FC-93, FC-95, FC-98, FC-129, FC-135, FC-170C, FC-430, FC-431, and FC-4430 (all manufactured by Sumitomo 3M Limited); Megafac F-470, F-1405, and F-474 (all manufactured by Dainippon Ink and Chemicals, Inc.); Zonyl FS-300, FSN, FSN-100, and FSO (all manufactured by DuPont); and Eftop EF-351, EF-352, EF-801, and EF-802 (all manufactured by Jemco). Among these, Zonyl FS-300, FSN, FSN-100, and FSO (all manufactured by DuPont) are particularly suitable because of their excellent reliability and improved color development.

[0198] Examples of silicone surfactants include modified silicones KF-351A, KF-353A, KF354L, KF355A, KF-615A, KF-640, KF-642, KF-643, and KF-6011 (all manufactured by Shin-Etsu Chemical Co., Ltd.); and silicones FZ-77, FZ-2104, FZ-2105, and L-7604 (all manufactured by Dow Corning Toray Co., Ltd.). Among these, KF-355A, KF-640, KF-642, and KF-643 (all manufactured by Shin-Etsu Kogyo Co., Ltd.) are particularly preferred because of their excellent reliability and improved color development.

[0199] The organic semiconductor film in the organic transistor according to one embodiment of the present invention is obtained by forming a film using a film-forming composition containing a conjugated polymer and a solvent.

[0200] The solvent is not particularly limited as long as it can dissolve or disperse the conjugated polymer in the solvent, and examples thereof include ether solvents such as diisopropyl ether, dibutyl ether, CPME, THF, 2-methyltetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, and tetralin; carbonate ester solvents such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, and methyl butyrate; Examples of suitable solvents include ester solvents such as toluene and γ-lactone; amide solvents such as DMF, DMAc, and NMP; urea solvents such as TMU and DMPU; sulfoxide solvents such as DMSO; alcohol solvents such as methanol, ethanol, 2-propanol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; halogenated solvents such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and o-DCB; nitromethane; and water, which may be mixed in any ratio. Among these, aromatic hydrocarbons and halogenated solvents are preferred because of their high boiling points and mild volatility, and toluene, xylene, mesitylene, cyclohexylbenzene, tetralin, 3,4-dimethylanisole, chlorobenzene, and o-DCB are more preferred.

[0201] There is no particular limitation on the amount of solvent used, and it is more preferable to add the solvent so that the concentration of the conjugated polymer is 0.001 to 95 weight percent, and more preferably a concentration appropriately selected from 0.01 to 30 weight percent.

[0202] The film-forming composition can be obtained by dissolving or dispersing a conjugated polymer in a solvent. Methods well known to those skilled in the art, such as stirring, shaking, or ball milling, can be used to dissolve or disperse the conjugated polymer in a solvent. Heating may be performed during this process.

[0203] The film-forming composition may contain a binder to improve film-forming properties. Examples of such binders include polymers such as polystyrene, poly-α-methylstyrene, polyvinylnaphthalene, poly(ethylene-co-norbornene), polymethyl methacrylate, polytriarylamine, and poly(9,9-dioctylfluorene-co-dimethyltriphenylamine). There are no particular restrictions on the concentration of the binder, but a concentration of 0.1 to 10.0 weight percent is preferred in terms of good coatability.

[0204] The method for forming a film using the film-forming composition is not particularly limited, and examples thereof include simple coating methods such as spin coating, drop casting, dip coating, and cast coating; and printing methods such as dispenser, inkjet, slit coating, blade coating, flexographic printing, screen printing, gravure printing, and offset printing; etc. Among these, spin coating, drop casting, and inkjet are preferred in terms of efficient film formation.

[0205] There is no particular limitation on the thickness of the organic semiconductor film, but in terms of increasing carrier mobility, the thickness is preferably 1 nm to 1000 nm, and more preferably 10 nm to 500 nm.

[0206] The organic transistor according to one aspect of the present invention may include a structural unit other than the gate electrode, the gate insulating film, the source electrode, the drain electrode, and the organic semiconductor film. Examples of the structural unit include a substrate, a base material, a bank material, and a protective film agent.

[0207] Examples of substrates include plastic substrates such as polyethylene terephthalate, polyethylene naphthalate, polymethyl methacrylate, polymethyl acrylate, polyethylene, polypropylene, polystyrene, cyclic polyolefin, polyimide, polycarbonate, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), poly(diisopropyl maleate), polyethersulfone, polyphenylene sulfide, and cellulose triacetate; inorganic substrates such as glass, quartz, aluminum oxide, silicon, highly doped silicon, silicon oxide, tantalum dioxide, tantalum pentoxide, and indium tin oxide; and metal substrates such as gold, copper, chromium, titanium, and aluminum. Of these, glass, silicon, and highly doped silicon are preferred, and glass is more preferred, in view of good transistor performance.

[0208] Figure 1 shows the structure of an element included in the organic transistor of the present invention. Here, 1001 denotes a bottom gate-top contact type, 1002 a bottom gate-bottom contact type, 1003 a top gate-top contact type, and 1004 a top gate-bottom contact type transistor element. 1 denotes an active layer (organic semiconductor film), 2 a substrate, 3 a gate electrode, 4 a first gate insulating film, 5 a source electrode, and 6 a drain electrode.

[0209] 2 shows the structure of an element included in the organic transistor of the present invention. Here, 2001 is a bottom gate-top contact type, 2002 is a bottom gate-bottom contact type, 2003 is a top gate-top contact type, and 2004 is a top gate-bottom contact type transistor element. 1 is an active layer (organic semiconductor film), 2 is a substrate, 3 is a gate electrode, 4 is a first gate insulating film, 5 is a source electrode, 6 is a drain electrode, and 7 is a second gate insulating film.

[0210] The organic transistor according to one embodiment of the present invention can be manufactured by a known manufacturing method, such as a manufacturing method using a film formation technique such as vacuum deposition, chemical vapor deposition (CVD), or spin coating.

[0211] [Summary] [1] A semiconductor device comprising a gate electrode, a source electrode, a drain electrode, and an organic semiconductor film, further comprising a first gate insulating film in contact with the organic semiconductor film, or a first gate insulating film in contact with the organic semiconductor film and a second gate insulating film not in contact with the organic semiconductor film, wherein the organic semiconductor film contains a conjugated polymer composed of a structural unit represented by the following general formula (2) and a structural unit represented by the following general formula (3), and wherein the interfacial energy between the first gate insulating film and the organic semiconductor film is 2.0 mJ / m ２ An organic transistor characterized by: (In the formula, A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (wherein X represents a divalent heteroaromatic ring linking group optionally substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms.) [2] The organic transistor according to [1], wherein the organic semiconductor film contains one or more surfactants selected from the group consisting of silicone surfactants, fluorine surfactants, and hydrocarbon surfactants. [3] The organic transistor according to [1] or [2], wherein the first gate insulating film contains one or more surfactants selected from the group consisting of silicone surfactants, fluorine surfactants, and hydrocarbon surfactants. [4] The organic transistor according to any one of [1] to [3], wherein the material used for the first gate insulating film is a cycloolefin copolymer represented by the following general formula (4z-1) or (4z-2): (s and t represent the number of repetitions, s is an integer of 1 or more, and t is an integer of 0 or more. R Ａ , R Ｂ R each independently represents hydrogen, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms. Ａ and R Ｂ and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.) [5] The organic transistor according to any one of [1] to [4], wherein in the structural unit represented by the general formula (2), either one or both of A and B is a linking group represented by the following general formulas (4-1) to (4-8): (J １ and J ２ each independently represents a chalcogen atom.) [6] The organic transistor according to any one of [1] to [5], wherein the structural unit represented by the general formula (2) is a structural unit represented by the following general formula (2-1): (R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.) [7] The organic transistor according to any one of [1] to [6], wherein the conjugated polymer is composed of a structural unit represented by the following general formula (24), and X in the general formula (24) is a linking group selected from the group consisting of the following general formulas (3-1) to (3-3): (In formula (24), A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (In formulas (3-1) to (3-3), R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and R ｈ each independently represents hydrogen, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms. [8] A conjugated polymer is composed of a structural unit represented by the following general formula (24): In the general formula (24), R １ , R ２ , R ３ and R ４ R each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms, A and B in the general formula (24) are linking groups represented by the following general formula (4-1), and X is a linking group selected from the group consisting of the following general formulas (3-1) to (3-3): (In formula (4-1), J １ independently represent chalcogen atoms.) (In formulas (3-1) to (3-3), R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and Rｈ each independently represents hydrogen, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms.) [9] The surface energy is 1.5 mJ / m ２ The organic transistor according to any one of [1] to [8], wherein:

[0212] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.

[0213] The molecular weight and molecular weight distribution of the conjugated polymers obtained in the examples were estimated by gel permeation chromatography (GPC). Commercially available reagents were used.

[0214] <NMR measurement conditions> Measurement device: Bruker ASCEND ＴＭ ADVANCE III HD (400 MHz) Measurement solvent: deuterated chloroform (CDCl ３ ) or deuterated DMSO (DMSO-d ６ ) Internal standard: tetramethylsilane (TMS)

[0215] [Synthesis reference example 1] To a mixture of methyl 3,4-diaminobenzoate (6.00 g, 36.1 mmol), triethylamine (20.0 mL, 143 mmol), and dichloromethane (180 mL), thionyl chloride (5.30 mL, 72.6 mmol) was added and the mixture was refluxed for 4 hours. The resulting mixture was cooled to room temperature, and then saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with chloroform. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / chloroform) to give methyl benzo-2,1,3-thiadiazole-5-carboxylate (4.49 g, 64%) as a white solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.76 (dd, J=1.6, 0.8Hz, 1H), 8.23 ​​(dd, J=9.2, 1.6Hz, 1H), 8.06 (dd, J=9.2, 0.8Hz, 1H), 4.02 (s, 3H).

[0216] [Synthesis reference example 2] To a mixture of 2,2,6,6-tetramethylpiperidine (880 μL, 5.17 mmol) and tetrahydrofuran (5.1 mL), 3.3 mL of a hexane solution of n-butyllithium (1.6 mol / L, 5.1 mmol) was added at −40° C., and the mixture was stirred at 0° C. for 30 minutes. Thereafter, a 2,2,6,6-tetramethylpiperidinyl magnesium chloride lithium chloride complex solution (5.1 mL, 5.1 mmol) was added, and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The solvent was distilled off from the resulting mixture under reduced pressure, and tetrahydrofuran (7.4 mL) was added to obtain TMP ２ A Mg·2LiCl solution was prepared.

[0217] To a mixture of methyl benzo-2,1,3-thiadiazole-5-carboxylate (1.50 g, 7.72 mmol) obtained in Synthesis Reference Example 1 and tetrahydrofuran (34 mL) was added TMP at −40° C. ２ A Mg·2LiCl solution was added and the mixture was stirred for 3.5 hours. Subsequently, under an argon stream, a zinc chloride solution (6.2 mL, 6.2 mmol), bis(dibenzylideneacetone)palladium(0) (59.0 mg, 103 μmol), tri(2-furyl)phosphine (48.0 mg, 207 μmol), and 1-bromo-4-iodobenzene (2.19 g, 7.74 mmol) were added and the mixture was stirred at 70°C for 15.5 hours. The resulting mixture was cooled to room temperature, and then saturated aqueous ammonium chloride solution was added and extracted with ethyl acetate. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / chloroform) to yield methyl 4-(4-bromophenyl)-2,1,3-benzothiadiazole-5-carboxylate (1.81 g, 69%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.08-8.03 (m, 2H), 7.65-7.63 (m, 2H), 7.36-7.26 (m, 2H), 3.72 (s, 3H).

[0218] [Synthesis reference example 3] To a mixture of methyl 4-(4-bromophenyl)-2,1,3-benzothiadiazole-5-carboxylate (900 mg, 2.58 mmol) obtained in Synthesis Reference Example 2 and dichloromethane (26 mL) was added diisobutylaluminum hydride (6.40 mL, 6.40 mmol) at -10°C, and the mixture was stirred for 3 hours. Methanol and an aqueous Rochelle salt solution were added to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was extracted with chloroform, and the collected organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give 4-(4-bromo-phenyl)-5-hydroxymethyl-2,1,3-benzothiadiazole (750 mg, 91%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.04 (d, J = 9.2Hz, 1H), 7.91 (d, J = 9.2Hz, 1H), 7.68-7.6 6 (m, 2H), 7.37-7.35 (m, 2H), 4.74 (d, J=5.6Hz, 2H), 1.77 (t, J=5.6Hz, 1H).

[0219] [Synthesis reference example 4] Trifluoromethanesulfonic acid (3.10 mL, 35.0 mmol) was added to a mixture of 4-(4-bromo-phenyl)-5-hydroxymethyl-2,1,3-benzothiadiazole (750 mg, 2.34 mmol) obtained in Synthesis Reference Example 3 and 1,2-dichloroethane (23 mL), and the mixture was stirred at 90°C for 3 hours. The resulting mixture was cooled to room temperature, and then a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with chloroform. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The solvent was evaporated under reduced pressure to give 8-bromo-6H-fluoreno[3,4-c][1,2,5]thiadiazole (591 mg, 84%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.40 (d, J = 8.0Hz, 1H), 7.98 (d, J = 8.4Hz, 1H), 7.81-7.78 (m, 2H), 7.66 (dd, J = 8.0, 1.6Hz, 1H), 4.05 (s, 2H).

[0220] [Synthesis Reference Example 5] To a mixture of 8-bromo-6H-fluoreno[3,4-c][1,2,5]thiadiazole (1.68 g, 5.54 mmol) obtained in Synthesis Reference Example 4 and tetrahydrofuran (28 mL), lithium diisopropylamide (11 mL, 11 mmol) was added at −10° C. and stirred for 1.5 hours. Then, 1-iodohexadecane (5.2 mL, 16.6 mmol) was added, and the mixture was stirred at room temperature for 24 hours. Water was added to the reaction solution, and the mixture was extracted with hexane. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / chloroform) to give 8-bromo-6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazole (2.38 g, 57%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.31 (d, J = 8.0Hz, 1H), 7.98 (d, J = 8.8Hz, 1H), 7.63-7.54 (m, 3H), 2 .05 (t, J=8.2Hz, 4H), 1.31-1.02 (m, 52H), 0.87 (t, J=7.0Hz, 6H), 0.64-0.47 (m, 4H).

[0221] [Synthesis Reference Example 6] To a mixture of 2,2,6,6-tetramethylpiperidine (0.62 mL, 3.7 mmol) and tetrahydrofuran (3.7 mL), 2.4 mL of a hexane solution of n-butyllithium (1.6 mol / L, 3.7 mmol) was added at -40°C, and the mixture was stirred at 0°C for 30 minutes. Then, a 2,2,6,6-tetramethylpiperidinyl magnesium chloride lithium chloride complex solution (3.7 mL, 3.7 mmol) was added, and the mixture was stirred at 0°C for 30 minutes and at room temperature for 1 hour. The solvent was distilled off from the resulting mixture under reduced pressure, and tetrahydrofuran (5.2 mL) was added to obtain TMP ２ A Mg·2LiCl solution was prepared.

[0222] To a mixture of methyl benzo-2,1,3-thiadiazole-5-carboxylate (713 mg, 3.67 mmol) obtained in Synthesis Reference Example 1 and tetrahydrofuran (11 mL) was added TMP at −40° C. ２A Mg·2LiCl solution was added and the mixture was stirred for 3 hours. Thereafter, under an argon stream, a zinc chloride solution (8.0 mL, 4.0 mmol), palladium(II) acetate (14 mg, 60 μmol), tri-t-butylphosphonium tetrafluoroborate (36 mg, 120 μmol), and 8-bromo-6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazole (2.30 g, 3.06 mmol) obtained in Synthesis Reference Example 5 were added, and the mixture was stirred at 70°C for 62 hours. The resulting mixture was cooled to room temperature, and then a saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / chloroform) to obtain a pale yellow solid of methyl (6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazo-8-yl)-2,1,3-benzothiadiazole-5-carboxylate (1.57 g, 60%). １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.61 (d, J = 7.2Hz, 1H), 8.08-7.99 (m, 3H), 7.98 (d, J = 8.8Hz, 1H), 7.62 (dd, J = 8.0, 1.6Hz, 1H), 7. 53 (d, J = 1.6 Hz, 1H), 3.63 (s, 3H), 2.13-2.08 (m, 4H), 1.30-1.10 (m, 52H), 0.87 (t, J = 7.0Hz, 6H), 0.82-0.60 (m, 4H).

[0223] [Synthesis Reference Example 7] To a mixture of methyl (6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazo-8-yl)-2,1,3-benzothiadiazole-5-carboxylate (1.50 g, 1.73 mmol) obtained in Synthesis Reference Example 6 and dichloromethane (17 mL) was added diisobutylaluminum hydride (4.3 mL, 4.3 mmol) at −10° C., and the mixture was stirred for 3.5 hours. Methanol and an aqueous Rochelle salt solution were added to the resulting mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was extracted with chloroform, and the collected organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give 8-(5-hydroxymethyl-2,1,3-benzothiadiazo-4-yl)-6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazole (1.30 g, 90%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.62 (d, J=7.6Hz, 1H), 8.06 (d, J=8.8Hz, 1H), 8.01 (d, J=8. 8Hz, 1H), 7.96 (d, J = 9.2Hz, 1H), 7.69 (d, J = 9.2Hz, 1H), 7.61 (dd, J = 7.6, 1.2H z, 1H), 7.54 (d, J = 1.2Hz, 1H), 4.83 (d, J = 5.6Hz, 2H), 2.17-2.04 (m, 4H), 1.76 (t, J=5.6Hz, 1H), 1.30-1.05 (m, 52H), 0.90-0.85 (m, 6H), 0.78-0.63 (m, 4H).

[0224] [Synthesis Reference Example 8] To a mixture of 8-(5-hydroxymethyl-2,1,3-benzothiadiazo-4-yl)-6,6-dihexadecyl-6H-fluoreno[3,4-c][1,2,5]thiadiazole (1.30 g, 1.55 mmol) obtained in Synthesis Reference Example 7 and 1,2-dichloroethane (16 mL) was added trifluoromethanesulfonic acid (2.0 mL, 23 mmol), and the mixture was stirred at room temperature for 3 hours. The resulting mixture was cooled to room temperature, and then a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with chloroform. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give (int-1-1-n16) (951 mg, 75%) as a pale yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.75 (s, 1H), 8.59 (s, 1H), 8.00-7.96 (m, 2H), 7.87 (d, J = 8.8Hz, 1H), 7.71 (d, J = 8.8Hz, 1H), 4.21 (s, 2H), 2.35-2.28 (m, 2H), 2.21-2.14 (m, 2H), 1.32-1.05 (m, 52H), 1.00-0.84 (m, 6H), 0.72-0.56 (m, 4H).

[0225] [Synthesis Reference Example 9] To a mixture of (int-1-1-n16) (900 mg, 1.10 mmol) obtained in Synthesis Reference Example 8 and tetrahydrofuran (22 mL), lithium diisopropylamide (2.2 mL, 2.4 mmol) was added at −10° C. and the mixture was stirred for 2.5 hours. Thereafter, 1-iodohexadecane (0.76 mL, 2.4 mmol) was added, and the mixture was stirred at room temperature for 17 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / chloroform) to give (mono-H-1-n16) (835 mg, 60%) as a pale yellow solid. １ H-NMR (CDCl ３, 400MHz) δ (ppm): 8.49 (s, 2H), 7.98 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 2H), 2.33-2.26 (m , 4H), 2.21-2.14 (m, 4H), 1.29-0.98 (m, 104H), 0.88 (t, J=7.0Hz, 12H), 0.71-0.58 (m, 8H).

[0226] [Synthesis Reference Example 10] To a mixture of (mono-H-1-n16) (800 mg, 0.631 mmol) obtained in Synthesis Reference Example 9, chloroform (8.4 mL), and hydrogen bromide (30% acetic acid solution) (4.2 mL), bromine (0.20 mL, 3.8 mmol) was added and the mixture was refluxed for 3 hours. The resulting mixture was cooled to room temperature, and then saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate were added, followed by extraction with chloroform. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane / chloroform) to give (mono-hal-1-n16) (832 mg, 92%) as a yellow solid. １ H-NMR (CDCl ３ , 400MHz) δ (ppm): 8.43 (s, 2H), 7.92 (s, 2H), 2.32-2.24 (m, 4H), 2.18-2.1 0 (m, 4H), 1.29-1.00 (m, 104H), 0.86 (t, J=7.0Hz, 12H), 0.66-0.58 (m, 8H).

[0227] [Synthesis Reference Example 11] A mixture of (mono-hal-1-n16) (110 mg, 77.0 μmol) obtained in Synthesis Reference Example 10, 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene (35.9 mg, 77.0 μmol), and chlorobenzene (2.0 mL) was bubbled with argon for 30 minutes. ２ (dba) ３ CHCl ３(1.6 mg, 1.5 μmol) and tri(o-tolyl)phosphine (1.9 mg, 6.2 μmol) were added, and the mixture was stirred at 180°C for 2 hours using a microwave reactor. Subsequently, 2-(tributylstannyl)thiophene (220 μL, 690 μmol) was added to the reaction solution, and the mixture was stirred at 180°C for 10 minutes using a microwave reactor. Furthermore, 2-bromothiophene (70 μL, 770 μmol) was added, and the mixture was stirred at 180°C for 10 minutes using a microwave reactor. The resulting mixture was cooled to room temperature and then precipitated in a mixed solution of methanol and concentrated hydrochloric acid (150 mL / 15 mL), and the precipitated solid was filtered. The resulting solid was subjected to Soxhlet extraction using methanol, acetone, hexane, and cyclohexane to remove components soluble in these solvents. Furthermore, the filter residue was dissolved in THF. The resulting mixture was concentrated under reduced pressure, and the precipitated solid was precipitated in methanol and filtered. The obtained solid was washed with methanol and then dried under reduced pressure at 90°C to obtain a black solid (3-1-6-n16) (38 mg, 35%). GPC (THF): Mn = 31,600 g / mol, Mw = 51,100 g / mol, PDI = 1.62. GPC (TCB, 140°C): Mn = 35,000 g / mol, Mw = 56,000 g / mol, PDI = 1.6.

[0228] Example 1 A 0.5 wt % o-DCB solution of the conjugated polymer (3-1-6-n16) synthesized in Synthesis Reference Example 11 was heated in a glove box under a nitrogen atmosphere to prepare a composition for forming an organic semiconductor film.

[0229] After cooling to room temperature, the entire amount was filtered through a 0.22 μm filter, which confirmed that the solution state was maintained and the compound was suitable for film formation.

[0230] Next, a Parylene C film was formed on a glass substrate as an underlayer by CVD. A shadow mask with a channel length of 100 μm and a channel width of 500 μm was then placed on the Parylene C layer, and silver was evaporated under vacuum to form source and drain electrodes. The solution prepared above was spin-coated in a nitrogen atmosphere in a glove box. This was heated to 150°C and held for 15 minutes to form an organic semiconductor film of a conjugated polymer (3-1-6-n16). Next, a 4 wt% toluene solution of TOPAS (Sigma-Aldrich) was spin-coated in air to form a first gate insulating film in contact with the organic semiconductor film. This was heated to 120°C and held for 10 minutes to form a TOPAS insulating film.

[0231] Furthermore, a film of Parylene C was formed as a second gate insulating film by the CVD method, and then a silver electrode was formed by evaporation, to create a top-gate-bottom-contact organic transistor (the gate electrode was silver, the gate insulating layer was TOPAS and Parylene C, and the source electrode and drain electrode were silver).

[0232] (Calculation of Interfacial Energy) The interfacial energy calculated from the contact angle of water and the contact angle of diiodomethane with respect to the organic semiconductor film, and the contact angle of water and the contact angle of diiodomethane with respect to the insulating film, was 0.34 mJ / m ２ It was.

[0233] (Measurement of Semiconductor and Electrical Properties) The organic transistor was connected to a semiconductor parameter analyzer (Keithley, Model 4200A-SCS) under atmospheric conditions, and the gate voltage (Vg) was scanned from +10 to -50 V in 1 V increments at a drain voltage (Vd = -50 V) to evaluate the transfer characteristics. The organic transistor exhibited p-type characteristics, and its hole carrier mobility was 7.05 cm ２ / Vs.

[0234] Example 2 The same procedure as in Example 1 was repeated, except that parylene was used instead of TOPAS for the first gate insulating film in contact with the organic semiconductor film, and gold was used for the source electrode and the drain electrode. The interfacial energy calculated from the contact angles of water and diiodomethane on the organic semiconductor film and the contact angles of water and diiodomethane on the insulating film was 1.48 mJ / m ２The obtained organic transistor exhibited p-type characteristics, and the carrier mobility of the hole was 1.76 cm ２ / Vs.

[0235] Example 3 The same procedure as in Example 1 was repeated, except that a 5 wt % m-xylene solution of polystyrene (Sigma-Aldrich) was used instead of a 4 wt % toluene solution of TOPAS to form the first gate insulating film in contact with the organic semiconductor film. The interfacial energy calculated from the contact angles of water and diiodomethane on the organic semiconductor film and the contact angles of water and diiodomethane on the insulating film was 1.26 mJ / m ２ The obtained organic transistor exhibited p-type characteristics, and its hole carrier mobility was 5.51 cm ２ / Vs.

[0236] Example 4 The same procedure as in Example 1 was repeated, except that a 5 wt % m-xylene solution (containing 0.5 wt % Poly(methylphenylsiloxane) [a silicone surfactant]) of an insulating material synthesized by the method described in WO 2023 / 074606 (Resin 1 in the publication) was used instead of a 4 wt % toluene solution of TOPAS to form the first gate insulating film in contact with the organic semiconductor film. The interfacial energy calculated from the contact angles of water and diiodomethane with the organic semiconductor film, and the contact angles of water and diiodomethane with the insulating film, was 0.82 mJ / m ２ The obtained organic transistor exhibited p-type characteristics, and its hole carrier mobility was 3.97 cm ２ / Vs.

[0237] Comparative Example 1 The same procedure as in Example 1 was repeated, except that a 5 wt % m-xylene solution of an insulating material synthesized by the method described in WO 2023 / 074606 (Resin 1 in the publication) was used instead of a 4 wt % toluene solution of TOPAS to form a first gate insulating film in contact with the organic semiconductor film. The interfacial energy calculated from the contact angles of water and diiodomethane with the organic semiconductor film and the contact angles of water and diiodomethane with the insulating film was 3.16 mJ / m ２The obtained organic transistor exhibited p-type characteristics, and its hole carrier mobility was 0.46 cm ２ / Vs.

[0238] REFERENCE SIGNS LIST 1 Active layer (organic semiconductor film) 2 Substrate 3 Gate electrode 4 First gate insulating film 5 Source electrode 6 Drain electrode 7 Second gate insulating film

Claims

1. A semiconductor device comprising a gate electrode, a source electrode, a drain electrode and an organic semiconductor film, further comprising a first gate insulating film in contact with the organic semiconductor film, or a first gate insulating film in contact with the organic semiconductor film and a second gate insulating film not in contact with the organic semiconductor film, the organic semiconductor film containing a conjugated polymer composed of a structural unit represented by the following general formula (2) and a structural unit represented by the following general formula (3), and the interface energy between the first gate insulating film and the organic semiconductor film is 2.0 mJ / m ２ An organic transistor characterized in that: (In the formula, A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ Each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (In the formula, X represents a divalent heteroaromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms.) 2. The organic transistor according to claim 1, wherein the organic semiconductor film contains one or more surfactants selected from the group consisting of silicone-based surfactants, fluorine-based surfactants and hydrocarbon-based surfactants.

3. The organic transistor according to claim 1, wherein the first gate insulating film contains one or more surfactants selected from the group consisting of silicone-based surfactants, fluorine-based surfactants and hydrocarbon-based surfactants.

4. The organic transistor according to claim 1, wherein the material used for the first gate insulating film is a cycloolefin copolymer represented by the following general formula (4z-1) or (4z-2): (s and t represent the number of repetitions, s is an integer of 1 or more, and t is an integer of 0 or more. R Ａ , R Ｂ R each independently represents a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms. Ａ and R Ｂ may be bonded to each other to form a ring together with the carbon atoms to which they are attached.

5. The organic transistor according to claim 1, wherein in the structural unit represented by the general formula (2) in the organic semiconductor film, either or both of A and B are linking groups represented by the following general formulas (4-1) to (4-8). (J １ and J. ２ each independently represents a chalcogen atom.) 6. The organic transistor according to claim 1, wherein the structural unit represented by the general formula (2) in the organic semiconductor film is a structural unit represented by the following general formula (2-1): (R １ , R ２ , R ３ and R ４ Each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ may be bonded to each other to form a ring together with the carbon atoms to which they are attached.

7. The organic transistor according to claim 1, wherein the conjugated polymer in the organic semiconductor film is composed of a structural unit represented by the following general formula (24), and X in the general formula (24) is a linking group selected from the group consisting of the following general formulas (3-1) to (3-3): In formula (24), A and B each independently represent a monovalent aromatic ring linking group which may be substituted with an alkyl group having 1 to 50 carbon atoms or an alkoxy group having 1 to 50 carbon atoms; R １ , R ２ , R ３ and R ４ Each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms. (In formulas (3-1) to (3-3), R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and R ｈ each independently represents a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms.

8. The conjugated polymer in the organic semiconductor film is composed of a structural unit represented by the following general formula (24): In the general formula (24), R １ , R ２ , R ３ and R ４ Each independently represents an alkyl group having 1 to 50 carbon atoms. １ and R ２ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ３ and R ４ and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. ５ and R ６ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 50 carbon atoms, A and B in the general formula (24) are linking groups represented by the following general formula (4-1), and X is a linking group selected from the group consisting of the following general formulas (3-1) to (3-3): (In formula (4-1), J １ each independently represents a chalcogen atom.) (In formulas (3-1) to (3-3), R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ and R ｈ each independently represents a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, or an alkoxy group having 1 to 50 carbon atoms.

9. The surface energy is 1.5 mJ / m ２ 2. The organic transistor of claim 1 , wherein: