Aromatic compound, organic semiconductor layer, and organic thin-film transistor

Abstract

Provided is an aromatic compound which is an organic semiconductor material of a coating application type having high carrier mobility, high heat resistance, and high solubility.　The aromatic compound is represented by formula (5) or formula (5-2). Only one among the combinations of adjacent two of R25 to R28 constitutes formula (6) to form a five- or six-membered ring, and only one among the combinations of adjacent two of R29 to R32 constitutes formula (6-2) to form a five- or six-membered ring. X7 represents an oxygen atom, etc.; Y4 represents CR37, etc.; R25 to R33 each represent a hydrogen atom, etc.; and R33 is a group represented by formula (2). k and m are each 0 or 1 and l is an integer of 1-20.

Description

Aromatic compound, organic semiconductor layer, and organic thin film transistor

[0001] The present invention relates to novel aromatic compounds that can be applied to electronic materials such as organic semiconductor materials, organic semiconductor layers using the same, and organic thin-film transistors. In particular, the present invention relates to aromatic compounds having specific substituents that have excellent solubility and heat resistance and are therefore applicable to various device fabrication processes, and organic semiconductor layers and organic thin-film transistors using the same.

[0002] Organic semiconductor devices, typified by organic thin-film transistors, have attracted attention in recent years because they offer features not found in inorganic semiconductor devices, such as energy conservation, low cost, and flexibility. These organic semiconductor devices are composed of several materials, including an organic semiconductor layer, a substrate, an insulating layer, and electrodes. Among these, the organic semiconductor layer, which is responsible for the transport of charge carriers, plays a central role in the device. Since the performance of organic semiconductor devices depends on the carrier mobility of the organic semiconductor material that constitutes this organic semiconductor layer, the development of organic semiconductor materials that provide high carrier mobility is desired.

[0003] 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 organic materials are dissolved in a suitable solvent and the resulting solution is coated. Of these, the coating method can be carried out using printing technology without using high temperature and high vacuum conditions, and is therefore expected to significantly reduce the manufacturing costs of device fabrication, making it an economically preferable process.

[0004] From the viewpoint of high carrier mobility and the device fabrication process, the organic semiconductor material used in such a coating method preferably has heat resistance of 130°C or higher and a solubility of 0.1% by weight or higher at room temperature. Furthermore, in the case of a transistor used for electronic paper, the carrier mobility is preferably 0.1 cm. ２ It is preferable that the voltage is 1 / V·sec or more.

[0005] It is generally known that small molecule semiconductors with a rod-shaped molecular long axis of a fused ring system tend to exhibit high carrier mobility due to their higher crystallinity compared to polymer semiconductors. Currently, proposed small molecule materials include 2,7-dialkyl-substituted benzothienobenzothiophenes (see, for example, Patent Document 1 and Non-Patent Document 1), 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophenes (see, for example, Non-Patent Document 2), and dithienobiphenylene derivatives (see, for example, Patent Document 2).

[0006] WO2008 / 047896 publication WO2021 / 177417 publication

[0007] Journal of the American Chemical Society, 2007, Vol. 129, pp. 15732-15733 Journal of the American Chemical Society, 2006, Vol. 128, pp. 12604-12605

[0008] However, small molecule semiconductors generally suffer from low solubility. To address this issue, semiconductors incorporating alkyl groups to improve solubility have been reported, but these have the drawback of reduced carrier mobility and heat resistance. Semiconductors incorporating aromatic substituents to achieve high carrier mobility through π-stacking have also been reported, but these have been reported to significantly reduce solubility in exchange for high mobility. Therefore, few small molecule organic semiconductor materials are known that combine high carrier mobility, high heat resistance, and high solubility.

[0009] For example, the dialkyl-substituted benzothienobenzothiophenes described in Patent Document 1 and Non-Patent Document 1 have a problem with heat resistance in that transistor operation is lost when heated to 130° C. or higher.

[0010] The 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophene described in Non-Patent Document 2 is generally hardly soluble in organic solvents, and has a problem with solubility.

[0011] Furthermore, the alkyl-substituted dithienobiphenylene derivatives described in Patent Document 2 have both high heat resistance and moderate solubility and can be suitably used in organic semiconductors, but compounds with even higher solubility are desired in order to be applicable to a wide range of device fabrication processes.

[0012] The present invention has been made in view of the above problems, and an object of the present invention is to provide a novel coating-type organic semiconductor material that has high carrier mobility, high heat resistance, and high solubility.

[0013] As a result of intensive research to solve the above problems, the present inventors have found that novel aromatic compounds having specific substituents can be used as organic semiconductor materials that not only provide high carrier mobility but also have high heat resistance and high solubility, and have thus completed the present invention.

[0014] That is, the present invention relates to an aromatic compound represented by the following formula (5) or the following formula (5-2), an organic semiconductor layer containing the aromatic compound, and an organic thin-film transistor including the organic semiconductor layer.

[0015]

[0016] [(where R ２５ ~R ２８ Among the combinations of adjacent two of these, only one pair constitutes the following formula (6), and R ２９ ~R ３２ Among the combinations of adjacent two of R, only one pair constitutes the following formula (6-2), forming a 5-membered ring or a 6-membered ring, respectively. ２５ ~R ３２ and R ６９ , R ７０ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the formula (2).

[0017]

[0018] (wherein k and m each independently represent 0 or 1, and l represents an integer from 1 to 20.)

[0019]

[0020] (where X ７ is an oxygen atom, a sulfur atom, a selenium atom, CR ３４ =CR ３５ , or NR ３６ Indicates Y ４ is CR ３７ or a nitrogen atom. ３４ ~R ３７ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the formula (2), R ３３ is a group represented by the formula (2).

[0021]

[0022] (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｂ represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by the formula (2).

[0023] The novel aromatic compounds of the present invention not only provide high carrier mobility but also have high heat resistance and solubility, making it possible to provide organic thin-film transistors that exhibit excellent semiconductor properties when applied.

[0024] 1A and 1B are diagrams illustrating the cross-sectional structure of an organic thin film transistor.

[0025] The present invention will be described in detail below.

[0026] [1. Aromatic Compound] The present invention is an aromatic compound represented by the above formula (5) or (5-2) (hereinafter referred to as "the compound of the present invention").

[0027] In formulas (5) and (5-2), R ２５ ~R ２８ Among the combinations of adjacent two of R, only one pair constitutes the above formula (6), and R ２９ ~R ３２ Of the combinations of two adjacent groups, only one group constitutes the above formula (6-2), forming a 5-membered ring or a 6-membered ring, respectively.

[0028] R that did not constitute the formula (6) and the formula (6-2) ２５ ~R ３２ and R ６９ , R ７０ , R in formula (6) and formula (6-2) ３４ ~R ３７ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2).

[0029] R ３３ is a group represented by formula (2).

[0030] R ３３ｂ is a group represented by one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by formula (2). ３３ｂ is preferably one selected from the group consisting of alkyl groups having 1 to 20 carbon atoms and groups represented by formula (2), since this will result in higher carrier mobility in the compound of the present invention.

[0031] In the aromatic compound represented by formula (5) or formula (5-2), formula (6-2) is preferably the following formula (6-3).

[0032]

[0033] (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ It has the same meaning as R ３３ｃ represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. ３３ｃ is one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. ３３ｃ is preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, since this will result in the compound of the present invention having higher carrier mobility.

[0034] In the aromatic compound represented by formula (5) or formula (5-2), formula (6-2) is also preferably the following formula (6-4).

[0035]

[0036] (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｄ is an alkylaryl group having 5 to 28 carbon atoms or a group represented by the formula (2). ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R ７０ , R３３ｂ , R ３３ｃ The halogen atom in represents, for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and is preferably either a fluorine atom or a chlorine atom since the compound of the present invention is stable.

[0037] The R ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R ７０ , R ３３ｂ , R ３３ｃ Examples of the alkyl group having 1 to 20 carbon atoms in the formula (I) include linear, branched, or cyclic alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, n-hexyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-octadecyl, 2-ethylhexyl, 3-ethylheptyl, 3-ethyldecyl, 2-hexyldecyl, cyclopentyl, cyclohexyl, and cycloheptyl. Among these, the alkyl group is preferably an alkyl group having 1 to 14 carbon atoms, since this will result in the compound of the present invention becoming an aromatic compound that brings about higher carrier mobility and exhibits higher solubility, and more preferably a linear alkyl group having 1 to 14 carbon atoms, such as a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-tridecyl group, or n-tetradecyl group.

[0038] The R ３３ｂ , R ３３ｃExamples of the haloalkyl group having 1 to 20 carbon atoms in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 3,3,3-trifluoropropyl group, a 1,1-difluoropropyl group, a perfluoroisopropyl group, a 2,2,2-trifluoro-1- (trifluoromethyl)ethyl group, perfluorocyclopropyl group, 2,2,3,3-tetrafluorocyclopropyl group, perfluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 4,4,4-trifluorobutyl group, 1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl group, 1-(trifluoromethyl)propyl group, 1-methyl-3,3,3-trifluoropropyl group, perfluorocyclobutyl group a 2,2,3,3,4,4-hexafluorocyclobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, a 4,4,5,5,5-pentafluoropentyl group, a 5,5,5-trifluoropentyl group, a 1,2,2,3,3,3-hexafluoro-1-(perfluoroethyl)propyl group, a 2,2,3,3,3-pentafluoro-1-(perfluoroethyl)propyl group, a perfluoro Examples include a cyclopentyl group, a perfluorohexyl group, a 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, a 3,3,4,4,5,5,6,6,6-nonafluorohexyl group, a 4,4,5,5,6,6,6-heptafluorohexyl group, a 5,5,6,6,6-peptafluorohexyl group, a 6,6,6-trifluorohexyl group, a perfluorocyclohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a 2-chloroethyl group, and a 3-bromopropyl group.

[0039] The R ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R７０ , R ３３ｂ , R ３３ｃ Examples of the alkenyl group having 2 to 20 carbon atoms in the formula (I) include ethenyl, propenyl, butenyl, 2-methylpropenyl, n-pentenyl, 2-methylbutenyl, n-hexenyl, 2-methylpentenyl, n-heptenyl, n-octenyl, 2-ethylhexenyl, n-nonenyl, 2-ethylheptenyl, n-decenyl, n-dodecenyl, cyclopentenyl-1-group, cyclohexenyl-1-group, and cycloheptenyl-1-group.

[0040] The R ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R ７０ , R ３３ｂ , R ３３ｃ Examples of the alkynyl group having 2 to 20 carbon atoms include an ethynyl group, a propynyl group, a butynyl group, an n-pentynyl group, an n-hexynyl group, an n-heptynyl group, an n-octynyl group, an n-nonynyl group, an n-decynyl group, and an n-dodecynyl group.

[0041] The R ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R ７０ , R ３３ｂ , R ３３ｃ Examples of the alkadienyl group having 4 to 22 carbon atoms in the formula (I) include a butadienyl group, a pentadienyl group, a hexadienyl group, an n-heptadienyl group, an n-octadienyl group, an n-nonadienyl group, an n-decadienyl group, an n-dodecadienyl group, and an n-tridecadienyl group. An alk-1,3-dienyl group having 4 to 22 carbon atoms is preferred, and a hexa-1,3-dienyl group, an n-hepta-1,3-dienyl group, an n-octa-1,3-dienyl group, an n-nona-1,3-dienyl group, or an n-deca-1,3-dienyl group is more preferred.

[0042] The R ２５ ~R ３２ , R ３４ ~R ３７ , R６９ , R ７０ , R ３３ｂ , R ３３ｃ Examples of the alkadiynyl group having 4 to 22 carbon atoms in the formula (I) include a butadiynyl group, a pentadiynyl group, a hexadiynyl group, an n-heptadiynyl group, an n-octadiynyl group, an n-nonadiynyl group, an n-decadiynyl group, an n-dodecadiynyl group, an n-tridecadiynyl group, and the like. A 1,3-alkadiynyl group having 4 to 22 carbon atoms is preferred, and a hexa-1,3-diynyl group, an n-hepta-1,3-diynyl group, an n-octa-1,3-diynyl group, an n-nona-1,3-diynyl group, or an n-deca-1,3-diynyl group is more preferred.

[0043] The R ２５ ~R ３２ , R ３４ ~R ３７ , R ６９ , R ７０ , R ３３ｂ , R ３３ｃThe aryl group having 4 to 26 carbon atoms in the formula (I) includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include a phenyl group; alkyl-substituted phenyl groups such as a p-tolyl group, a p-(n-hexyl)phenyl group, a p-(n-octyl)phenyl group, and a p-(2-ethylhexyl)phenyl group; a 2-furyl group, a 2-thienyl group; a 5-methyl-2-furyl group, a 5-ethyl-2-furyl group, a 5-(n-propyl)-2-furyl group, a 5-(n -butyl)-2-furyl group, 5-(n-pentyl)-2-furyl group, 5-(n-hexyl)-2-furyl group, 5-(n-octyl)-2-furyl group, 5-(2-ethylhexyl)-2-furyl group, 5-methyl-2-thienyl group, 5-ethyl-2-thienyl group, 5-(n-propyl)-2-thienyl group, 5-(n-butyl)-2-thienyl group, 5-(n-pentyl)- Examples include alkyl-substituted heteroaryl groups such as a 2-thienyl group, a 5-(n-hexyl)-2-thienyl group, a 5-(n-octyl)-2-thienyl group, and a 5-(2-ethylhexyl)-2-thienyl group; halogen-substituted aryl groups such as a 5-fluoro-2-phenyl group, a 5-fluoro-2-furyl group, a 5-fluoro-2-thienyl group, a 4-fluoro-2-phenyl group, a 4-fluoro-2-furyl group, and a 4-fluoro-2-thienyl group; and haloalkyl-substituted aryl groups such as a 5-trifluoromethyl-2-phenyl group, a 5-trifluoromethyl-2-furyl group, a 5-trifluoromethyl-2-thionyl group, a 4-trifluoromethyl-2-phenyl group, a 4-trifluoromethyl-2-furyl group, and a 4-trifluoromethyl-2-thionyl group.

[0044] The R ３３ｂ , R ３３ｄ Examples of the alkylaryl group having 5 to 28 carbon atoms in the formula (I) include a 4-methylphenethyl group, a 4-ethylphenethyl group, a 4-propylphenethyl group, a 4-butylphenethyl group, a 4-pentylphenethyl group, a 4-hexylphenethyl group, a 4-heptylphenethyl group, a 4-octylphenethyl group, a 4-nonylphenethyl group, and a 4-decylphenethyl group.

[0045] The R ２５ ~R ３２ , R ６９ , R ７０is preferably one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), in order to provide a higher solubility for the compound of the present invention; more preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; and even more preferably a hydrogen atom or a methyl group.

[0046] The R ３４ ~R ３７ is preferably one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), in order to ensure the stability of the compound of the present invention. Furthermore, in order to provide the compound of the present invention with higher carrier mobility, R ３４ ~R ３７ is more preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2), and R ３４ ~R ３７ It is even more preferred that is a hydrogen atom.

[0047] X in formulas (6) and (6-2) to (6-4) ７ is an oxygen atom, a sulfur atom, a selenium atom, CR ３４ =CR ３５ , or NR ３６ A sulfur atom, an oxygen atom, a sulfur atom, or a selenium atom is preferred because the compound of the present invention exhibits higher solubility. Furthermore, X is preferred because the compound of the present invention exhibits high carrier mobility. ７ is more preferably a sulfur atom.

[0048] Y in formulas (6) and (6-2) to (6-4) ４ is CR ３７ or a nitrogen atom, and CR for the stability of the compound of the present invention. ３７ is preferred.

[0049] Of the aromatic compounds represented by either formula (5) or formula (5-2), the aromatic compound represented by formula (5-2) is preferred because the compound of the present invention exhibits higher mobility.

[0050] In formula (2), k and m each independently represent 0 or 1, and from the viewpoint of ease of synthesis of the compound of the present invention, k is preferably 0. Furthermore, it is more preferable that both k and m are 0, since this will result in the compound of the present invention having higher carrier mobility.

[0051] In formula (2), l represents an integer of 1 to 20, and l is preferably an integer of 1 to 3 because the compound of the present invention exhibits higher solubility. Furthermore, l is more preferably an integer of 1 to 2 because the compound of the present invention exhibits higher heat resistance. Furthermore, l is more preferably 2 because the compound of the present invention exhibits higher carrier mobility.

[0052] In formula (2), it is preferable that k and m are both 0 and l is 2. This allows the compound of the present invention to exhibit higher carrier mobility.

[0053] The group represented by formula (2) is preferably a 3,3-dimethylbutyl group, a 4,4-dimethylpentyl group, or a 2,2-dimethylpropyl group, since these groups provide the compound of the present invention with higher carrier mobility. Furthermore, a 3,3-dimethylbutyl group is more preferred, since these groups provide the compound of the present invention with higher heat resistance and higher solubility.

[0054] In addition, the aromatic compound represented by formula (5) or formula (5-2) is preferably one compound selected from the group consisting of the following formulas (7-1) to (7-6) in terms of ease of synthesis, and is particularly preferably a compound represented by formula (7-5).

[0055]

[0056] (where X ８ , X ９ are each independently an oxygen atom, a sulfur atom, a selenium atom, and NR ４４ Y represents one selected from the group consisting of ５ , Y ６ are each independently CR ４５ or a nitrogen atom. ３８ ~R ４５ , R ７１ , R ７２each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by formula (2), R ３８ and R ４１ At least one of the X's in the formulas (7-1) to (7-6) is a group represented by formula (2). ８ , X ９ are each independently an oxygen atom, a sulfur atom, a selenium atom, and NR ４４ In order to ensure the stability of the compound of the present invention, a sulfur atom, an oxygen atom, a sulfur atom, or a selenium atom is preferred. Furthermore, in order to provide the compound of the present invention with higher carrier mobility, X ８ , X ９ is more preferably a sulfur atom.

[0057] Y in formulas (7-1) to (7-6) ５ , Y ６ are each independently CR ４５ or nitrogen atom, and for the stability of the compounds of the present invention, CR ４５ is preferred.

[0058] R in formulas (7-1) to (7-6) ３８ ~R ４５ , R ７１ , R ７２ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by the above formula (2); R ３８ ~R ４５ At least one of the groups is a group represented by the above formula (2).

[0059] R in formulas (7-1) to (7-6) ３８ , R４１ and either one or both of them are a group represented by formula (2).

[0060] The definition of the group represented by formula (2) in formulas (7-1) to (7-6) is the same as the definition of formula (2) in the above formulas (5) and (5-2).

[0061] The R ３８ ~R ４５ , R ７１ , R ７２ The halogen atom in represents, for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and is preferably either a fluorine atom or a chlorine atom since the compound of the present invention is stable.

[0062] The R ３８ ~R ４５ , R ７１ , R ７２ Examples of the alkyl group having 1 to 20 carbon atoms in the formula (I) include linear, branched, or cyclic alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, n-hexyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-octadecyl, 2-ethylhexyl, 3-ethylheptyl, 3-ethyldecyl, 2-hexyldecyl, cyclopentyl, cyclohexyl, and cycloheptyl. Among these, the alkyl group is preferably an alkyl group having 1 to 14 carbon atoms, since this will result in the compound of the present invention being an aromatic compound that brings about higher carrier mobility and exhibits higher solubility, and more preferably a linear alkyl group having 1 to 14 carbon atoms, such as a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-tridecyl group, or n-tetradecyl group.

[0063] The R ３８ ~R ４５ , R ７１ , R ７２Examples of the haloalkyl group having 1 to 20 carbon atoms in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 3,3,3-trifluoropropyl group, a 1,1-difluoropropyl group, a perfluoroisopropyl group, a 2,2,2-trifluoro-1- (trifluoromethyl)ethyl group, perfluorocyclopropyl group, 2,2,3,3-tetrafluorocyclopropyl group, perfluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 4,4,4-trifluorobutyl group, 1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl group, 1-(trifluoromethyl)propyl group, 1-methyl-3,3,3-trifluoropropyl group, perfluorocyclobutyl group a 2,2,3,3,4,4-hexafluorocyclobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, a 4,4,5,5,5-pentafluoropentyl group, a 5,5,5-trifluoropentyl group, a 1,2,2,3,3,3-hexafluoro-1-(perfluoroethyl)propyl group, a 2,2,3,3,3-pentafluoro-1-(perfluoroethyl)propyl group, a perfluoro Examples include a cyclopentyl group, a perfluorohexyl group, a 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, a 3,3,4,4,5,5,6,6,6-nonafluorohexyl group, a 4,4,5,5,6,6,6-heptafluorohexyl group, a 5,5,6,6,6-peptafluorohexyl group, a 6,6,6-trifluorohexyl group, a perfluorocyclohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a 2-chloroethyl group, and a 3-bromopropyl group.

[0064] The R ３８ ~R ４５ , R ７１ , R ７２Examples of the alkenyl group having 2 to 20 carbon atoms in the formula (I) include ethenyl, propenyl, butenyl, 2-methylpropenyl, n-pentenyl, 2-methylbutenyl, n-hexenyl, 2-methylpentenyl, n-heptenyl, n-octenyl, 2-ethylhexenyl, n-nonenyl, 2-ethylheptenyl, n-decenyl, n-dodecenyl, cyclopentenyl-1-group, cyclohexenyl-1-group, and cycloheptenyl-1-group.

[0065] The R ３８ ~R ４５ , R ７１ , R ７２ Examples of the alkynyl group having 2 to 20 carbon atoms include an ethynyl group, a propynyl group, a butynyl group, an n-pentynyl group, an n-hexynyl group, an n-heptynyl group, an n-octynyl group, an n-nonynyl group, an n-decynyl group, and an n-dodecynyl group.

[0066] The R ３８ ~R ４５ , R ７１ , R ７２ Examples of the alkadienyl group having 4 to 22 carbon atoms in the formula (I) include a butadienyl group, a pentadienyl group, a hexadienyl group, an n-heptadienyl group, an n-octadienyl group, an n-nonadienyl group, an n-decadienyl group, an n-dodecadienyl group, and an n-tridecadienyl group. An alk-1,3-dienyl group having 4 to 22 carbon atoms is preferred, and a hexa-1,3-dienyl group, an n-hepta-1,3-dienyl group, an n-octa-1,3-dienyl group, an n-nona-1,3-dienyl group, or an n-deca-1,3-dienyl group is more preferred.

[0067] The R ３８ ~R ４５ , R ７１ , R ７２Examples of the alkadiynyl group having 4 to 22 carbon atoms in the formula (I) include a butadiynyl group, a pentadiynyl group, a hexadiynyl group, an n-heptadiynyl group, an n-octadiynyl group, an n-nonadiynyl group, an n-decadiynyl group, an n-dodecadiynyl group, an n-tridecadiynyl group, and the like. A 1,3-alkadiynyl group having 4 to 22 carbon atoms is preferred, and a hexa-1,3-diynyl group, an n-hepta-1,3-diynyl group, an n-octa-1,3-diynyl group, an n-nona-1,3-diynyl group, or an n-deca-1,3-diynyl group is more preferred.

[0068] The R ３８ ~R ４５ , R ７１ , R ７２The aryl group having 4 to 26 carbon atoms in the formula (I) includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include a phenyl group; alkyl-substituted phenyl groups such as a p-tolyl group, a p-(n-hexyl)phenyl group, a p-(n-octyl)phenyl group, and a p-(2-ethylhexyl)phenyl group; a 2-furyl group, a 2-thienyl group; a 5-methyl-2-furyl group, a 5-ethyl-2-furyl group, a 5-(n-propyl)-2-furyl group, a 5-(n -butyl)-2-furyl group, 5-(n-pentyl)-2-furyl group, 5-(n-hexyl)-2-furyl group, 5-(n-octyl)-2-furyl group, 5-(2-ethylhexyl)-2-furyl group, 5-methyl-2-thienyl group, 5-ethyl-2-thienyl group, 5-(n-propyl)-2-thienyl group, 5-(n-butyl)-2-thienyl group, 5-(n-pentyl)- Examples include alkyl-substituted heteroaryl groups such as a 2-thienyl group, a 5-(n-hexyl)-2-thienyl group, a 5-(n-octyl)-2-thienyl group, and a 5-(2-ethylhexyl)-2-thienyl group; halogen-substituted aryl groups such as a 5-fluoro-2-phenyl group, a 5-fluoro-2-furyl group, a 5-fluoro-2-thienyl group, a 4-fluoro-2-phenyl group, a 4-fluoro-2-furyl group, and a 4-fluoro-2-thienyl group; and haloalkyl-substituted aryl groups such as a 5-trifluoromethyl-2-phenyl group, a 5-trifluoromethyl-2-furyl group, a 5-trifluoromethyl-2-thionyl group, a 4-trifluoromethyl-2-phenyl group, a 4-trifluoromethyl-2-furyl group, and a 4-trifluoromethyl-2-thionyl group.

[0069] The R ３８ ~R ４５ , R ７１ , R ７２ Examples of the alkylaryl group having 5 to 28 carbon atoms in the formula (I) include a 4-methylphenethyl group, a 4-ethylphenethyl group, a 4-propylphenethyl group, a 4-butylphenethyl group, a 4-pentylphenethyl group, a 4-hexylphenethyl group, a 4-heptylphenethyl group, a 4-octylphenethyl group, a 4-nonylphenethyl group, and a 4-decylphenethyl group.

[0070] The R ３８ ~R ４５ , R７１ , R ７２ is preferably one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), in order to ensure the stability of the compound of the present invention. ３８ ~R ４５ , R ７１ , R ７２ is more preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2). In view of the higher carrier mobility of the compound of the present invention, R ３８ , R ４１ is preferably one selected from the group consisting of the group represented by the above formula (2), a hydrogen atom, and an alkyl group having 1 to 20 carbon atoms, and more preferably one selected from the group consisting of the group represented by the above formula (2) and an alkyl group having 1 to 20 carbon atoms, and R ３８ is a group represented by the above formula (2), and R ４１ It is more preferable that R is an alkyl group having 1 to 20 carbon atoms. ３９ , R ４０ , R ４２ ~R ４５ , R ７１ , R ７２ It is even more preferred that is selected from the group consisting of a hydrogen atom and a methyl group, with a hydrogen atom being even more preferred.

[0071] Among the formulae (7-1) to (7-6), the formula (7-1), (7-2) or (7-5) is preferred because the compound of the present invention exhibits higher solubility. Furthermore, the formula (7-5) is more preferred because the compound of the present invention provides higher carrier mobility.

[0072] The compound of the present invention can provide an aromatic compound that has high carrier mobility, high heat resistance, and high solubility. This effect is extremely high. In this specification, "high carrier mobility" means a carrier mobility of 0.10 cm ２ / V·sec or more, preferably 0.50 cm ２ / V·sec or more, more preferably 1.00 cm ２ / V·sec or more. In this specification, "high solubility" means that the solubility in a solvent (e.g., toluene) at room temperature is 0.1 wt % or more, preferably 1.0 wt % or more. In this specification, "high heat resistance" means that the melting point is 130°C or more.

[0073] Specific examples of the compound of the present invention include the following.

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] Among these, the following compounds are preferred.

[0087]

[0088]

[0089]

[0090]

[0091] Among these, the following compounds are particularly preferred.

[0092]

[0093] As a method for producing the compound of the present invention, any method can be used as long as it is possible to produce the compound.

[0094] As an example of the method for producing the aromatic compound of the present invention, for example, X ８ , X ９ is a sulfur atom, and Y ５ , Y ６ is CH and R ３８ is a group represented by formula (2), and R ３９ , R ４０ , R ４１ , R ４２ , R ４３ , R ７１ , R ７２ is a hydrogen atom, and m and k in formula (2) are each 0, can be produced by a method including the following steps A1 or B1 and C1. (Step A1): A step of producing a boronic acid ester by reacting an alkyl bromide derivative with bis(pinacolato)diboron in the presence of a copper catalyst and a ligand. (Step B1): A step of producing a boronic acid ester by reacting an alkene with borane and water to form a boronic acid, and then reacting the boronic acid with pinacol. (Step C1): A step of producing the aromatic compound (7-5a) by reacting the boronic acid ester obtained in step A1 or step B1 with 2-bromoanthra[1,2-b:5,6-b']dithiophene in the presence of a base and a palladium catalyst.

[0095] Details of each step are shown below: (Step A1) Step A1 is a step of producing a boronic acid ester by reacting an alkyl bromide derivative with bis(pinacolato)diboron in the presence of a copper catalyst and a ligand.

[0096] In this case, examples of the copper catalyst include copper(I) iodide, copper(I) bromide, copper(I) chloride, etc. Examples of the ligand include Xantphos, Ruphos, Xphos, etc.

[0097] Examples of the alkyl bromide derivative in Step A1 include (2-bromoethyl)cyclohexane, (3-bromopropyl)cyclohexane, (2-bromoethyl)cyclopentane, (3-bromopropyl)cyclopentane, etc. (Step B1) Step B1 is a step in which an alkene is reacted with borane and water to form a boronic acid, which is then reacted with pinacol to produce a boronic acid ester.

[0098] The boronic acid can be prepared, for example, by using 1 to 3 equivalents of borane in a solvent such as tetrahydrofuran (hereinafter abbreviated as THF) or diethyl ether at a temperature ranging from 0°C to 40°C.

[0099] In addition, during the reaction of boronic acid with pinacol, magnesium sulfate, sodium sulfate, or the like can be added as a dehydrating agent.

[0100] Examples of the alkene in Step B1 include vinylcyclohexane, allylcyclohexane, vinylcyclopentane, allylcyclopentane, etc. (Step C1) Step C1 is a step of producing an aromatic compound (7-5a) by Suzuki coupling reaction of the boronic acid ester obtained in Step A1 or B1 with 2-bromoanthra[1,2-b:5,6-b']dithiophene in the presence of a palladium catalyst.

[0101] The reaction can be carried out in a solvent such as toluene, N,N-dimethylformamide (hereinafter abbreviated as DMF), N,N-dimethylacetamide (hereinafter abbreviated as DMA), THF, etc., at a temperature range of 20° C. to 100° C. Water may be added as a solvent.

[0102] Examples of the palladium catalyst in Step C1 include palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and dichlorobis(triphenylphosphine)palladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, or the like can be added as the ligand.

[0103] Examples of the base used in Step C1 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0104] A more specific production method that is preferred from the viewpoint of ease of synthesis is shown in the following reaction scheme.

[0105]

[0106]

[0107]

[0108] (wherein l has the same meaning as l in formula (2)). In addition, as another example of the method for producing the aromatic compound of the present invention, for example, X ８ , X ９ is a sulfur atom, and Y ５ , Y ６ is CH and R ３８ , R ４１ is a group represented by formula (2), and R ３９ , R ４０ , R ４２ , R ４３ , R ７１ , R ７２ Aromatic compound (7-5b) in which m is a hydrogen atom and m and k in formula (2) are each 0 can be produced by a method that includes the above-mentioned step A1 or B1 and the following step C2: (Step C2): A step of producing aromatic compound (7-5b) by reacting the boronic acid ester obtained in step A1 or B1 with 2,8-dibromoanthra[1,2-b:5,6-b']dithiophene in the presence of a palladium catalyst.

[0109] Details of each step are shown below: (Step C2) Step C2 is a step of producing an aromatic compound (7-5b) by Suzuki coupling reaction of the boronic acid ester obtained in Step A1 or B1 with 2,8-bromoanthra[1,2-b:5,6-b']dithiophene in the presence of a base and a palladium catalyst.

[0110] The reaction can be carried out in a solvent such as toluene, DMF, DMA, or THF at a temperature ranging from 20° C. to 100° C. Water may also be added as a solvent.

[0111] Examples of the palladium catalyst in step C2 include palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and dichlorobis(triphenylphosphine)palladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, or the like can be added as the ligand.

[0112] Examples of the base used in Step C2 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0113] A more specific reaction in step C2, which is preferred from the viewpoint of ease of synthesis, is shown in the following reaction scheme.

[0114]

[0115] (wherein l has the same meaning as l in formula (2)). In addition, as another example of the method for producing the aromatic compound of the present invention, for example, X ８ , X ９ is a sulfur atom, and Y ５ , Y ６ is CH and R ３８ is a group represented by formula (2), and R ３９ , R ４０ , R ４２ , R ４３ , R ７１ , R ７２Aromatic compound (7-5d) in which m and k in formula (2) are each 0 and n is a hydrogen atom can be produced by a method including Steps D1 and C3, or Step C4, as described below. (Step D1): A step of converting an anthradithiophene derivative (7-5a) into a monolithium salt with n-butyllithium or tert-butyllithium, followed by synthesizing a monobromoanthradithiophene derivative (7-5c) using a brominating agent. (Step C3): A step of reacting a boronic acid ester or a boronic acid with the monobromoanthradithiophene derivative (7-5c) obtained in Step D1 in the presence of a base and a palladium catalyst to produce aromatic compound (7-5d). (Step C4): A step of reacting the boronic acid ester obtained in Step A1 or Step B1 described above with the monobromoanthradithiophene derivative in the presence of a base and a palladium catalyst to produce aromatic compound (7-5d).

[0116] Details of each step are shown below: (Step D1) Step D1 is a method of converting an anthradithiophene derivative into a monolithium salt with one equivalent of n-butyllithium or tert-butyllithium, and then reacting this with a brominating agent to produce a monobromo derivative.

[0117] The monolithium salt can be prepared, for example, by using 0.5 to 1.5 equivalents of n-butyllithium or tert-butyllithium in a solvent such as THF or diethyl ether at a temperature ranging from -80°C to 30°C.

[0118] Examples of brominating agents that can be used include tetrabromomethane, 1,2-dibromotetrachloroethane, etc. (Step C3) Step C3 is a step of producing an aromatic compound (7-5d) by Suzuki coupling reaction of a boronic acid ester or a boronic acid with the monobromoanthradithiophene derivative (7-5c) obtained in Step D1 in the presence of a palladium catalyst.

[0119] The reaction can be carried out in a solvent such as toluene, DMF, DMA, or THF at a temperature ranging from 20° C. to 100° C. Water may also be added as a solvent.

[0120] Examples of the palladium catalyst in step C3 include palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and dichlorobis(triphenylphosphine)palladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, or the like can be added as the ligand.

[0121] Examples of the base used in Step C3 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide, etc. (Step C4) Step C4 is a step of producing aromatic compound (7-5d) by Suzuki coupling reaction of the boronic acid ester obtained in Step A1 or B1 above with a monobromoanthradithiophene derivative in the presence of a palladium catalyst.

[0122] The reaction can be carried out in a solvent such as toluene, DMF, DMA, or THF at a temperature ranging from 20° C. to 100° C. Water may also be added as a solvent.

[0123] Examples of the palladium catalyst in step C4 include palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and dichlorobis(triphenylphosphine)palladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, or the like can be added as the ligand.

[0124] Examples of the base used in Step C4 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide, and the like.

[0125] The specific production methods for steps D1, C3 and C4, which are preferred from the viewpoint of ease of synthesis, are shown in the following reaction scheme.

[0126]

[0127]

[0128]

[0129] (wherein l has the same meaning as l in formula (2), and R ４５ is R shown in formula (7-5) ４５ and (5-2) are equivalent to the above.) [2. Solution for Forming an Organic Semiconductor Layer] One aspect of the present invention may be a solution for forming an organic semiconductor layer containing the compound of the present invention. The solution for forming an organic semiconductor layer can be prepared by dissolving the compound of the present invention in a solvent. Any solvent may be used as the solvent as long as it is capable of dissolving the aromatic compound represented by formula (5) or formula (5-2). Among these, organic solvents having a boiling point of 100°C or higher at normal pressure are preferred, as this allows for a favorable drying rate of the solvent when forming an organic semiconductor layer.

[0130] The solvent that can be used in the organic semiconductor layer-forming solution of the present invention is not particularly limited, and examples thereof include aromatic hydrocarbons such as toluene, mesitylene, o-xylene, isopropylbenzene, pentylbenzene, cyclohexylbenzene, 1,2,4-trimethylbenzene, tetralin, and indane; aromatic ethers such as anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, 2,6-dimethylanisole, ethylphenyl ether, butylphenyl ether, 1,2-methylenedioxybenzene, and 1,2-ethylenedioxybenzene; aromatic halogen compounds such as chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, 1,2-difluorobenzene, 1,3-difluorobenzene, and 1,4-difluorobenzene; thiophene, 3-chlorothiophene, 2-chlorothiophene, 3-methylthiophene, 2-methylthiophene, benzothiophene, 2-methylbenzothiophene, 2,3-dihydrobenzothiophene, and furan. Heteroaromatics such as 3-methylfuran, 2-methylfuran, 2,5-dimethylfuran, benzofuran, 2-methylbenzofuran, 2,3-dihydrobenzofuran, thiazole, oxazole, benzothiazole, benzoxazole, and pyridine; saturated hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and decalin; glycols such as dipropylene glycol dimethyl ether, dipropylene glycol diacetate, dipropylene glycol methyl-n-propyl ether, dipropylene glycol methyl ether acetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate;Examples of the ester include dimethyl phthalate, diethyl phthalate, dimethyl terephthalate, phenyl acetate, cyclohexanol acetate, 3-methoxybutyl acetate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl propionate, and γ-butyrolactone; and cyclic ethers such as THF and 2-methoxymethyltetrahydrofuran. Among these, toluene, o-xylene, mesitylene, 1,2,4-trimethylbenzene, tetralin, indan, octane, nonane, decane, anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, 2,6-dimethylanisole, ethyl phenyl ether, butyl phenyl ether, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, 3-methylthiophene, and benzothiazole are preferred because they have an appropriate drying rate, and toluene, o-xylene, mesitylene, tetralin, indan, octane, nonane, decane, anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, and 2,6-dimethylanisole are more preferred.

[0131] The solvent used in the organic semiconductor layer forming solution may be one type of solvent alone, or a mixture of two or more types of solvents having different properties such as boiling point, polarity, and solubility parameter may be used.

[0132] The temperature at which the aromatic compound represented by formula (5) or formula (5-2) is mixed and dissolved in a solvent is preferably in the range of 0 to 80°C, more preferably in the range of 10 to 60°C, in order to promote dissolution.

[0133] The time for dissolving and mixing the aromatic compound represented by formula (5) or formula (5-2) in the solvent is preferably 1 minute to 1 hour in order to obtain a homogeneous solution.

[0134] The concentration of the aromatic compound represented by formula (5) or formula (5-2) in the organic semiconductor layer-forming solution is preferably in the range of 0.1 to 10.0 wt %, more preferably 0.2 to 2.0 wt %, because it is easier to handle and more efficient in forming the organic semiconductor layer, and more preferably in the range of 0.5 to 1.5 wt %. Furthermore, the viscosity of the organic semiconductor layer-forming solution is preferably in the range of 0.3 to 10 mPa s, more preferably 0.5 to 5.0 mPa s, because it exhibits more favorable coatability.

[0135] Furthermore, since the aromatic compound itself has moderate cohesion properties, the solution can be prepared at a relatively low temperature. Furthermore, since the solution is oxidation-resistant, it is suitable for use in the production of organic thin films by coating. In other words, since there is no need to remove air from the atmosphere, the coating process can be simplified. Furthermore, a polymer can be present in the solution as a binder. Examples of such polymers include polystyrene, poly(α-methylstyrene), poly(4-methylstyrene), poly(1-vinylnaphthalene), poly(2-vinylnaphthalene), poly(styrene-block-butadiene-block-styrene), poly(styrene-block-isoprene-block-styrene), poly(vinyltoluene), poly(styrene-co-2,4-dimethylstyrene), poly(chlorostyrene), poly(styrene-co-α-methylstyrene), poly(styrene-co-butadiene), poly(ethylene-co-norbornene), polyphenylene ether, polycarbonate, and polycarbazole. Examples of suitable polymers include methyl methacrylate, poly(styrene-co-methyl methacrylate), polyethyl methacrylate, poly(n-propyl methacrylate), poly(isopropyl methacrylate), poly(n-butyl methacrylate), poly(phenyl methacrylate), polymethyl acrylate, polyethyl acrylate, poly(n-propyl acrylate), polar cyclic polyolefins, polysulfones, acrylonitrile-styrene copolymers, and methyl methacrylate-styrene copolymers. Among these, polystyrene, poly(α-methylstyrene), poly(ethylene-co-norbornene), and polymethyl methacrylate are preferred. The concentration of these polymers is preferably 0.001 to 10.0% by weight in order to achieve an appropriate viscosity of the solution.

[0136] The glass transition temperature (Tg) of the polymer is preferably 105°C or higher, more preferably 120°C or higher, and particularly preferably 150°C or higher, as this is more suitable for handling process temperatures during the manufacture of electronic devices.

[0137] Furthermore, since the molecular weight of the polymer is suitable for obtaining an organic thin-film transistor with higher carrier mobility, it is preferably 5,000 to 1,000,000, more preferably 10,000 to 500,000, and particularly preferably 20,000 to 100,000. In the present invention, the molecular weight of the polymer refers to the weight average molecular weight (Mw) in terms of polystyrene.

[0138] The polymer has the effect of a general binder and improves the film-forming properties of the resulting organic semiconductor layer, and insulating polymers and semiconducting polymers can also be used.

[0139] More specifically, the polar cyclic polyolefins mentioned as one of the above polymers are more preferably polar cyclic polyolefins represented by the following formula (9):

[0140]

[0141] (where R ６２ ~R ６４ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a nitro group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a hydroxyl group, an amino group, and an alkylamino group having 1 to 20 carbon atoms. Z represents one selected from the group consisting of a halogen atom, an alkyloxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a nitro group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a hydroxyl group, an amino group, and an alkylamino group having 1 to 20 carbon atoms. p represents an integer of 20 to 5,000, and q and r each independently represent an integer of 0 to 2. A bond consisting of a solid line and a dotted line indicates a single bond or a double bond.) R in formula (9) ６２ ~R ６４each independently represents one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a nitro group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a hydroxyl group, an amino group, and an alkylamino group having 1 to 20 carbon atoms, and a hydrogen atom or an alkyl group having 1 to 20 carbon atoms is preferred in view of the high heat resistance of the present polymer.

[0142] R ６２ ~R ６４ Examples of the halogen atom in the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 20 carbon atoms include a linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and an n-pentyl group. Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a p-tolyl group, a p-(n-hexyl)phenyl group, a p-(n-octyl)phenyl group, and a p-(2-ethylhexyl)phenyl group. Examples of the alkyloxycarbonyl group having 2 to 20 carbon atoms include a methyloxycarbonyl group, an ethyloxycarbonyl group, and an n-propyloxycarbonyl group. Examples of the aryloxycarbonyl group having 7 to 20 carbon atoms include a phenoxycarbonyl group and a 4-methylphenoxycarbonyl group. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and an n-propoxy group. Examples of the aryloxy group having 6 to 20 carbon atoms include a phenoxy group and a 4-methylphenoxy group. Examples of the alkylamino group having 1 to 20 carbon atoms include a methylamino group, an ethylamino group, and an n-propylamino group. Among these, the substituent R ６２ is preferably a methyl group, an ethyl group or an n-propyl group, and the substituent R ６３ and R ６４ is preferably a hydrogen atom.

[0143] Z in formula (9) represents one selected from the group consisting of a halogen atom, an alkyloxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a nitro group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a hydroxyl group, an amino group, and an alkylamino group having 1 to 20 carbon atoms.

[0144] Examples of the halogen atom in the substituent Z include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of alkyloxycarbonyl groups having 2 to 20 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an n-butoxycarbonyl group, an n-hexyloxycarbonyl group, and a cyclohexyloxycarbonyl group. Examples of aryloxycarbonyl groups having 7 to 20 carbon atoms include a phenoxycarbonyl group, a 4-methylphenoxycarbonyl group, a 2,4-dimethylphenoxycarbonyl group, and a 4-ethylphenoxycarbonyl group. Examples of alkoxy groups having 1 to 20 carbon atoms include a methoxy group and an ethoxy group. Examples of aryloxy groups having 6 to 20 carbon atoms include a phenoxy group and a 4-methylphenoxy group. Examples of the alkylamino group having 1 to 20 carbon atoms include a methylamino group, an ethylamino group, an n-propylamino group, etc. In order to achieve high solubility and high heat resistance of the present polymer, Z is preferably an alkyloxycarbonyl group having 2 to 20 carbon atoms.

[0145] p represents an integer of 20 to 5,000, and is preferably 40 to 2,000 because this is suitable for obtaining an organic thin-film transistor with higher carrier mobility. q represents an integer of 0 to 2, and is preferably 1. r represents an integer of 0 to 2, and is preferably 0 or 1, and more preferably 0.

[0146] A bond consisting of a solid line and a dotted line indicates a single bond or a double bond, and is preferably a single bond for thermal stability.

[0147] The polysulfones mentioned as one of the polymers above are not particularly limited as long as they have a polysulfone structure, and more specific examples include polysulfones represented by the following polysulfones 1 to 5.

[0148]

[0149] (wherein the substituent R ６５ ~R ６８ each independently represents an alkyl group having 1 to 20 carbon atoms, and s represents an integer of 10 to 20,000. ６５ ~R ６８ Examples of the alkyl group having 1 to 20 carbon atoms in the formula (I) include linear or branched alkyl groups such as methyl, ethyl, n-propyl, n-butyl, isobutyl, n-pentyl, n-hexyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-octadecyl, 2-ethylhexyl, 3-ethylheptyl, 3-ethyldecyl, and 2-hexyldecyl.

[0150] s represents an integer of 10 to 20,000, preferably an integer of 10 to 10,000.

[0151] The acrylonitrile-styrene copolymer mentioned as one of the above polymers is a copolymer of acrylonitrile and styrene in any ratio. In the finally obtained organic thin-film transistor, the weight ratio of acrylonitrile to styrene in the acrylonitrile-styrene copolymer is preferably 10:90 to 50:50, and more preferably 20:80 to 40:60, because this copolymer exhibits good electrical properties and improves reliability, such as by reducing the change in threshold voltage when bias stress is applied.

[0152] The methyl methacrylate-styrene copolymer mentioned as one of the above polymers is a copolymer of methyl methacrylate and styrene in any ratio. In the finally obtained organic thin-film transistor, the copolymer preferably has a molar ratio of methyl methacrylate to styrene of 1:99 to 90:10, more preferably 1:99 to 70:30, because this copolymer exhibits good electrical properties and improves reliability, such as by reducing the change in threshold voltage when bias stress is applied.

[0153] The polymer used as the binder may be a polymer whose surface energy has been adjusted by a surface treatment agent. Examples of the surface treatment agent include silane coupling agents, such as 1,1,1,3,3,3-hexamethyldisilazane, phenyltrimethoxysilane, octyltrichlorosilane, β-phenethyltrichlorosilane, and β-phenethyltrimethoxysilane.

[0154] The polymer may be a single polymer or a mixture of two or more polymers. Furthermore, polymers of different molecular weights may be mixed and used. [3. Organic Semiconductor Layer] One aspect of the present invention may be an organic semiconductor layer containing the compound of the present invention. Examples of methods for forming an organic semiconductor layer include a method of forming an organic semiconductor layer using an organic semiconductor layer-forming solution. The coating method for forming an organic semiconductor layer using an organic semiconductor layer-forming solution is not particularly limited as long as it can form an organic semiconductor layer. Examples of the coating method 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. Among these, spin coating, drop casting, and inkjet are preferred because they allow for easy and efficient formation of an organic semiconductor layer.

[0155] The organic semiconductor layer-forming solution of the present invention is applied to form a coating of the organic semiconductor layer-forming solution, and then the solvent is dried and removed from the coating, thereby forming an organic semiconductor layer containing the compound of the present invention formed using the organic semiconductor layer-forming solution.

[0156] When the solvent is removed by drying from the coating of the organic semiconductor layer-forming solution, there are no particular limitations on the drying conditions, and the solvent can be removed by drying under normal pressure or reduced pressure, for example.

[0157] There are no particular limitations on the temperature at which the solvent is dried and removed from the coating of the organic semiconductor layer-forming solution, but it is preferable to perform the drying and removal at a temperature in the range of 10 to 150°C, since this allows the solvent to be dried and removed efficiently from the applied organic semiconductor layer and enables the formation of an organic semiconductor layer.

[0158] When the solvent is dried and removed from the coating of the organic semiconductor layer-forming solution, the crystal growth of the aromatic compound represented by formula (5) or formula (5-2) can be controlled by adjusting the evaporation rate of the solvent to be removed.

[0159] The resulting organic semiconductor layer may be subjected to annealing treatment at 40 to 180° C. after the organic semiconductor layer is formed.

[0160] There is no limitation to the film thickness of the organic semiconductor layer of the present invention, and it is preferably in the range of 1 nm to 1 μm, more preferably in the range of 10 nm to 300 nm, since good carrier mobility can be obtained.

[0161] [4. Organic Thin Film Transistor] The organic semiconductor layer according to one embodiment of the present invention can be used as an organic semiconductor device comprising the organic semiconductor layer, particularly as an organic thin film transistor comprising the organic semiconductor layer and containing the compound of the present invention.

[0162] An organic thin-film transistor can be obtained by laminating an organic semiconductor layer provided with a source electrode and a drain electrode and a gate electrode on a substrate via an insulating layer. By using an organic semiconductor layer formed from the organic semiconductor layer-forming solution of the present invention as the organic semiconductor layer, an organic thin-film transistor that exhibits excellent semiconductor properties and electrical properties can be obtained.

[0163] 1 shows the cross-sectional structure of a typical organic thin-film transistor, where 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 organic thin-film transistor, 1 an organic semiconductor layer, 2 a substrate, 3 a gate electrode, 4 a gate insulating layer, 5 a source electrode, and 6 a drain electrode, and the organic semiconductor layer formed from the organic semiconductor layer-forming solution of the present invention can be applied to any of these organic thin-film transistors.

[0164] The substrate is not particularly limited, and examples thereof include plastic substrates such as polyethylene terephthalate, polyethylene naphthalate, polymethyl methacrylate, polymethyl acrylate, polyethylene, polypropylene, polystyrene, cyclic polyolefin, fluorinated cyclic polyolefin, polyimide, polycarbonate, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), poly(diisopropyl maleate), polyethersulfone, polyphenylene sulfide, and cellulose triacetate; inorganic material 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. When highly doped silicon is used as the substrate, the substrate can also serve as the gate electrode.

[0165] The material for the gate electrode is not particularly limited, and examples thereof include inorganic materials such as aluminum, gold, silver, copper, highly doped silicon, tin oxide, indium oxide, indium tin oxide, chromium, titanium, tantalum, graphene, and carbon nanotubes; and organic materials such as doped conductive polymers (e.g., PEDOT-PSS).

[0166] The inorganic materials described above can also be used without any problems as metal nanoparticle inks. In this case, the solvent is preferably a polar solvent such as water, methanol, ethanol, 2-propanol, 1-butanol, or 2-butanol; an aliphatic hydrocarbon solvent having 6 to 14 carbon atoms such as hexane, heptane, octane, decane, dodecane, or tetradecane; or an aromatic hydrocarbon solvent having 7 to 14 carbon atoms such as toluene, xylene, mesitylene, ethylbenzene, pentylbenzene, hexylbenzene, octylbenzene, cyclohexylbenzene, tetralin, indane, anisole, 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, 1,2-dimethylanisole, 2,3-dimethylanisole, or 3,4-dimethylanisole, to provide adequate dispersibility. After application, the nanoparticle ink is preferably annealed at a temperature ranging from 80°C to 200°C to improve conductivity.

[0167] The material for the gate insulating layer is not particularly limited, and examples thereof include inorganic materials 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; polymethyl methacrylate, polymethyl acrylate, polyimide, polyamic acid polycarbonate, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), polyethylene terephthalate, polyethylene naphthalate, poly Examples of suitable polymer insulating materials include ethyl cinnamate, polymethyl cinnamate, polyethyl crotonate, polyethersulfone, polypropylene-co-1-butene, polyisobutylene, polypropylene, polycyclopentane, polycyclohexane, polycyclohexane-ethylene copolymer, polyfluorinated cyclopentane, polyfluorinated cyclohexane, polyfluorinated cyclohexane-ethylene copolymer, BCB resin (trade name: Cyclotene, manufactured by Dow Chemical Company), Cytop (registered trademark), Teflon (registered trademark), and Parylene (registered trademark) such as Parylene C. Among these, polymer insulating materials that can be applied by a coating method (polymer gate insulating layer) are preferred for the gate insulating layer, as they can be produced by a simple method.

[0168] The solvent used to dissolve the polymer insulating material is not particularly limited, and examples thereof include aliphatic hydrocarbon solvents having 6 to 14 carbon atoms, such as hexane, heptane, octane, decane, dodecane, and tetradecane; ether-based solvents, such as THF, 1,2-dimethoxyethane, and dioxane; alcohol-based solvents, such as ethanol, isopropyl alcohol, 1-butanol, 2-butanol, 2-ethylhexanol, and tetrahydrofurfuryl alcohol; ketone-based solvents, such as acetone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, and acetophenone; ester-based solvents, such as ethyl acetate, γ-butyrolactone, cyclohexanol acetate, 3-methoxybutyl acetate, tetrahydrofurfuryl acetate, and tetrahydrofurfuryl propionate; amide-based solvents, such as DMF and NMP; Examples of the solvent include glycol-based solvents such as propylene glycol dimethyl ether, dipropylene glycol diacetate, dipropylene glycol methyl-n-propyl ether, dipropylene glycol methyl ether acetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate; and fluorinated solvents such as perfluorohexane, perfluorooctane, 2-(pentafluoroethyl)hexane, and 3-(pentafluoroethyl)heptane.

[0169] The concentration of the polymer insulating material when dissolved in a solvent is, for example, 0.1 to 10.0% by weight at a temperature of 20 to 40° C. There is no limit to the film thickness of the insulating layer obtained at this concentration, and from the viewpoint of insulation resistance, it is preferably 100 nm to 1 μm, and more preferably 150 nm to 900 nm.

[0170] The gate insulating layer may be one whose surface has been modified with, for example, silanes such as octadecyltrichlorosilane, decyltrichlorosilane, decyltrimethoxysilane, octyltrichlorosilane, octadecyltrimethoxysilane, β-phenethyltrichlorosilane, β-phenethyltrimethoxysilane, phenyltrichlorosilane, or phenyltrimethoxysilane; phosphonic acids such as octadecylphosphonic acid, decylphosphonic acid, or octylphosphonic acid; or silylamines such as hexamethyldisilazane. Generally, surface treatment of the gate insulating layer increases the crystal grain size of the organic semiconductor material and improves molecular orientation, thereby achieving favorable results such as improved carrier mobility, improved current on / off ratio, and lowered threshold voltage.

[0171] There are no particular limitations on the materials for the source electrode and the drain electrode, and the same material as the gate electrode can be used. Within the gate electrode, the source electrode and the drain electrode may be the same or different, or different materials may be stacked. Furthermore, to increase the carrier injection efficiency, the surfaces of the source electrode and the drain electrode can be subjected to a surface treatment. Examples of surface treatment agents used for the surface treatment include benzenethiol, pentafluorobenzenethiol, 4-fluorobenzenethiol, and 4-methoxybenzenethiol.

[0172] The organic thin film transistor of the present invention has a carrier mobility of 0.10 cm due to its fast operation. ２ / V·sec or more, and ２ / V·sec or more is more preferable, and ２ It is more preferable that the voltage is 1 / V·sec or more.

[0173] The organic thin-film transistor according to one embodiment of the present invention can be used in electronic materials such as organic semiconductor layers of transistors for electronic paper, organic EL displays, liquid crystal displays, IC tags (RFID tags), pressure sensors, biosensors, etc.; organic EL display materials; organic semiconductor laser materials; organic thin-film solar cell materials; photonic crystal materials; and semiconductor materials for image sensors. In addition, the aromatic compound represented by formula (5) or formula (5-2) forms a crystalline thin film, and is therefore preferably used as a semiconductor layer of an organic thin-film transistor.

[0174] [Summary] As can be understood from the above description, the present invention includes the following aspects. Aspect 1: An aromatic compound represented by either the above formula (5) or the above formula (5-2). [(In formulas (5) and (5-2), R ２５ ~R ２８ Of the combinations of adjacent two of these, only one pair constitutes the above formula (6), and R ２９ ~R ３２ Among the combinations of adjacent two of R, only one pair constitutes the above formula (6-2), forming a 5-membered ring or a 6-membered ring, respectively. ２５ ~R ３２ , and R ６９ and R ７０ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the above formula (2). (In formula (2), k and m each independently represent 0 or 1, and l represents an integer of 1 to 20.) (In formula (6), X ７ is an oxygen atom, a sulfur atom, a selenium atom, CR ３４ =CR ３５ , or NR ３６ Indicates Y ４ is CR ３７ or a nitrogen atom. ３４ ~R ３７each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the formula (2), R ３３ is a group represented by the formula (2). ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｂ represents one member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by formula (2). Aspect 2: The aromatic compound of aspect 1, wherein formula (6-2) is formula (6-3) above. (In formula (6-3), X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｃ represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms.) Aspect 3: The aromatic compound of Aspect 1, wherein the formula (6-2) is the above formula (6-4). (In formula (6-4), X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｄis an alkylaryl group having 5 to 28 carbon atoms or a group represented by the formula (2). Aspect 4: The aromatic compound of any one of Aspects 1 to 3, wherein the aromatic compound represented by the formula (5) or (5-2) is a compound represented by one selected from the group consisting of the formulas (7-1) to (7-6). (In the formulas (7-1) to (7-6), X ８ , X ９ are each independently an oxygen atom, a sulfur atom, a selenium atom, or NR ４４ Indicates Y ５ , Y ６ are each independently CR ４５ or a nitrogen atom. ３８ ~R ４５ , R ７１ , R ７２ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by formula (2), R ３８ and R ４１ At least one of R is a group represented by the formula (2). ３８ and R ４１ are each independently one selected from the group consisting of a group represented by formula (2), a hydrogen atom, and an alkyl group having 1 to 20 carbon atoms, and R ３９ , R ４０ , R ４２ ~R ４５ , R ７１ and R ７２ Aspect 6: The aromatic compound of aspect 4, wherein R is a hydrogen atom. ３８ and R ４１ is a group represented by the formula (2), and R ３９ , R ４０ , R ４２ ~R ４５ , R ７１ and R ７２is a hydrogen atom. Aspect 7: A solution for forming an organic semiconductor layer, comprising the aromatic compound of any one of Aspects 1 to 6. Aspect 8: An organic semiconductor layer, comprising the aromatic compound of any one of Aspects 1 to 6. Aspect 9: An organic thin film transistor, comprising the aromatic compound of any one of Aspects 1 to 6.

[0175] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0176] To identify the product １ H NMR spectroscopy and liquid chromatography-mass spectroscopy (LCMS) analysis were used.

[0177] < １ H NMR Spectroscopic Analysis> Apparatus: JEOL Ltd., (trade name) Delta V5 (400 MHz) Measurement temperature: 23°C (unless temperature is specified) <Liquid Chromatography-Mass Spectroscopic (LCMS) Analysis> Apparatus: Bruker Daltonics, (trade name) microTOF focus MS Ionization: Atmospheric Pressure Chemical Ionization (APCI) LC Conditions: Conditions described in the section on Liquid Chromatography Analysis below Thin layer chromatography, gas chromatography (GC), and liquid chromatography (LC) analyses were used to confirm the progress of the reaction. Liquid chromatography analysis was also used to measure the purity of the aromatic compounds.

[0178] <Thin-Layer Chromatography Analysis> Merck PLC silica gel 60F254 0.5 mm for thin-layer chromatography was used, and hexane and / or toluene were used as the developing solvent.

[0179] <Gas Chromatography Analysis> Apparatus: Shimadzu Corporation, product name: GC2025 Column: RESTEK, product name: Rxi-1HT, 30 m <Liquid Chromatography Analysis> Apparatus: Agilent Technologies, model: 1260 Infinity II Column: Tosoh, product name: ODS-100V, 5 μm, 4.6 mm×250 mm Column temperature: 33° C. Eluent: dichloromethane:acetonitrile=2:8 (volume ratio) Flow rate: 1.0 ml / min A recycle preparative HPLC apparatus was used for purification of aromatic compounds.

[0180] <Recycle Preparative HPLC> Apparatus: Japan Analytical Industry Co., Ltd., Model: LC-9160II NEXT Solvent: tetrahydrofuran Flow rate: 10 ml / min A differential scanning calorimeter (DSC) was used to measure the melting points of aromatic compounds.

[0181] <DSC Measurement> Apparatus: manufactured by SII Nano Technology Inc., model: DSC6220 Temperature increase / decrease rate: 10°C / min Scan range: -10°C to 300°C A semiconductor parameter analyzer was used to evaluate the transfer characteristics of aromatic compounds.

[0182] <Transfer characteristic measurement> Apparatus: Keithley, model: 4200A-SCS Drain voltage: -20V Gate voltage: 10V to -20V.

[0183] Synthesis Example 1 Synthesis of 2-(3,3-dimethylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Under a nitrogen atmosphere, 548 mg (0.948 mmol) of Xantphos (Tokyo Chemical Industry Co., Ltd.), 5.57 g (21.9 mmol) of bis(pinacolato)diboron (Tokyo Chemical Industry Co., Ltd.), 92.7 mg (0.936 mmol) of copper(I) chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), 2.48 g (22.1 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 25 ml of THF (Fujifilm Wako Pure Chemical Industries, dehydrated grade) were added to a 100 ml Schlenk reaction vessel and stirred at room temperature for 25 minutes. Under ice cooling, 3.02 g (18.3 mmol) of 1-bromo-3,3-dimethylbutane (Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 0°C for 35 minutes and then at room temperature for 3.5 hours. The reaction mixture was ice-cooled, and water and then toluene were added to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene) to obtain 3.01 g of 2-(3,3-dimethylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless liquid (yield: 76%).

[0184] １ H NMR (CDCl ３ ): 1.32-1.28 (m, 2H), 1.25 (s, 12H), 0.85 (s, 9H), 0.74-0.70 (m, 2H). 2-(3,3-dimethylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0185]

[0186] ​Example 1 Synthesis of 2-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 1) Under a nitrogen atmosphere, 669 mg of 2-bromoanthra[1,2-b:5,6-b′]dithiophene (Compound 22 in WO2021 / 177417) synthesized by the method described in the publication, 103 mg (0.460 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries), 426 mg (0.912 mmol) of Ruphos (Tokyo Chemical Industry), and 681 mg (6.07 mmol) of potassium tert-butoxide (Tokyo Chemical Industry) were placed in a 200 mL Schlenk tube. To this mixture were added 50 mL of a toluene solution (Fujifilm Wako Pure Chemical Industries, dehydrated grade) of 1.18 g (5.54 mmol) of 2-(3,3-dimethylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 1 and 2.5 mL of water, followed by stirring at 80°C for 20 hours. The reaction mixture was allowed to cool to room temperature, and insoluble matter was removed using diatomaceous earth (Fujifilm Wako Pure Chemical Industries), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane / toluene = 2 / 1). The resulting solid was separated by recycling HPLC and washed with methanol, yielding 330 mg of a yellow solid, 2-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 1) (yield: 48%).

[0187] １ H NMR (CDCl ３ ): δ = 8.70 (s, 1H), 8.61 (s, 1H), 7.89 (d, J = 8.8Hz, 1H), 7.87 (d, J = 8.7Hz, 1H), 7.82 (d, J = 8.8Hz, 1H), 7.72 (d, J = 8.8Hz) , 1H), 7.54 (d, J = 5.1Hz, 1H), 7.49 (d, J = 5.4Hz, 1H), 7.17 (s, 1H), 3.02-2.97 (m, 2H), 1.79-1.75 (m, 2H), 1.03 (s, 9H).

[0188] Melting point: 171°C (Compound 1)

[0189]

[0190] ​Example 2 Synthesis of 2,8-di(3,3-dimethylbutyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 2) Under a nitrogen atmosphere, 89.2 mg (0.199 mmol) of 2,8-dibromoanthra[1,2-b:5,6-b′]dithiophene synthesized by the method described in WO2021 / 177417 (Compound 20 in the publication), 14.2 mg (0.0632 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries), 59.6 mg (0.128 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 98.9 mg (0.881 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were placed in a 100 mL Schlenk tube. To this mixture were added 20 mL of a toluene solution (Fujifilm Wako Pure Chemical Industries, dehydrated grade) of 180 mg (0.846 mmol) of 2-(3,3-dimethylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 1 and 1.0 mL of water, followed by stirring at 80°C for 24 hours. The reaction mixture was allowed to cool to room temperature, and insoluble matter was removed using diatomaceous earth (Fujifilm Wako Pure Chemical Industries). The resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane / toluene = 2 / 1). The resulting solid was separated by recycling HPLC and purified by recrystallization from heptane, yielding 11.1 mg of a yellow solid, 2,8-di(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 2) (yield: 12%).

[0191] １ H NMR (CDCl ３ ): δ = 8.58 (s, 2H), 7.84 (d, J = 8.7Hz, 2H), 7.69 (d, J = 8.7Hz, 2H), 7.16 (s, 2H), 3.01-2.97 (m, 4H), 1.79-1.74 (m, 4H), 1.03 (s, 9H).

[0192] Melting point: 249°C (Compound 2)

[0193]

[0194] ​Example 3 Synthesis of 2-bromo-8-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 3) Under a nitrogen atmosphere, 454 mg (1.21 mmol) of 2-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 1) synthesized in Example 1 and 15 mL of THF (Fujifilm Wako Pure Chemical Industries, dehydrated grade) were added to a 100 mL Schlenk reaction vessel. The mixture was cooled to -78°C, and 2.00 mL (3.20 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries) was added, followed by stirring at -78°C for 3 hours. 1.20 g (3.70 mmol) of 1,2-dibromotetrachloroethane was added at -78°C, and the mixture was stirred while warming to room temperature. 1M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 506 mg of a yellow solid of 2-bromo-8-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (compound 3) (yield 91%).

[0195] １ H NMR (CDCl ３ ): δ = 8.59 (s, 1H), 8.52 (s, 1H), 7.86 (d, J = 8.7Hz, 1H), 7.84 (d, J = 8.7Hz, 1H), 7.72 (d, J = 8.7Hz, 1H), 7.69 (d, J = 8.7Hz, 1H), 7.46 (s, 1H), 7.18 (s, 1H), 3.01-2.97 (m, 2H), 1.79-1.74 (m, 2H), 1.03 (s, 9H). (Compound 3)

[0196]

[0197] ​Example 4 Synthesis of 2-(3,3-dimethylbutyl)-8-propylanthra[1,2-b:5,6-b']dithiophene (Compound 4) Under a nitrogen atmosphere, 53.2 mg (0.117 mmol) of Compound 3 synthesized in Example 3, 8.10 mg (0.0361 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 33.8 mg (0.0656 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 53.0 mg (0.0724 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 38.0 mg (0.432 mmol) of propylboronic acid (Tokyo Chemical Industry Co., Ltd.) were placed in a 50 mL Schlenk tube. 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, dehydrated grade) and 0.5 mL of water were added thereto, and the mixture was stirred at 80°C for 2.5 hours. The reaction mixture was allowed to cool to room temperature, and insoluble matter was removed using diatomaceous earth (Fujifilm Wako Pure Chemical Industries, Ltd.). The resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane / toluene = 2 / 1). The resulting solid was purified by recycling HPLC and recrystallized from heptane / ethanol to obtain 27.6 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-propylanthra[1,2-b:5,6-b']dithiophene (Compound 4) (yield: 56%).

[0198] １ H NMR (CDCl ３ ): δ = 8.58 (s, 2H), 7.84 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.70 (d, J = 8.7Hz, 1H), 7.16 (s, 2 H), 3.01-2.97 (m, 4H), 1.91-1.82 (m, 2H), 1.79-1.75 (m, 2H), 1.07 (t, J = 7.3Hz, 3H), 1.03 (s, 9H).

[0199] Melting point: 136°C (Compound 4)

[0200]

[0201] ​Example 5 Synthesis of 2-butyl-8-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 5) The same procedure as in Example 4 was repeated, except that butylboronic acid (Tokyo Chemical Industry Co., Ltd.) was used instead of propylboronic acid, to obtain 23.3 mg of a yellow solid, 2-butyl-8-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 5) (yield: 49%).

[0202] １ H NMR (CDCl ３ ): δ = 8.58 (s, 2H), 7.84 (d, J = 8.7Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.70 (d, J = 8.7Hz, 1H), 7.16 (s, 1H), 7.1 5 (s, 1H), 3.03-2.97 (m, 4H), 1.86-1.75 (m, 4H), 1.52-1.45 (m, 2H), 1.03 (s, 9H), 0.99 (t, J = 7.3Hz, 3H).

[0203] Melting point: 157°C (Compound 5)

[0204]

[0205] Example 6 Synthesis of 2-(3,3-dimethylbutyl)-8-pentylanthra[1,2-b:5,6-b']dithiophene (Compound 6) The same procedure as in Example 4 was repeated, except that pentylboronic acid (Tokyo Chemical Industry Co., Ltd.) was used instead of propylboronic acid, to obtain 19.8 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-pentylanthra[1,2-b:5,6-b']dithiophene (Compound 6) (yield: 46%).

[0206] １ H NMR (CDCl ３ ): δ = 8.58 (s, 2H), 7.84 (d, J = 8.7Hz, 2H), 7.70 (d, J = 8.9Hz, 1H), 7.69 (d, J = 8.7Hz, 1H), 7.16 (s, 1H), 7.1 5 (s, 1H), 3.03-2.97 (m, 4H), 1.88-1.71 (m, 4H), 1.52-1.38 (m, 4H), 1.03 (s, 9H), 0.94 (t, J = 7.0Hz, 3H).

[0207] ​​Melting point: 160°C (Compound 6)

[0208]

[0209] Example 7 Synthesis of 2-(3,3-dimethylbutyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 7) The same procedure as in Example 4 was repeated, except that hexylboronic acid (Tokyo Chemical Industry Co., Ltd.) was used instead of propylboronic acid, to obtain 139 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 7) (yield: 46%).

[0210] １ H NMR (CDCl ３ ): δ = 8.58 (s, 2H), 7.84 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.70 (d, J = 8.8Hz, 1H), 7.16 (s, 1H), 7.1 5 (s, 1H), 3.03-2.97 (m, 4H), 1.87-1.74 (m, 4H), 1.55-1.32 (m, 6H), 1.03 (s, 9H), 0.92 (t, J = 6.9Hz, 3H).

[0211] Melting point: 136°C (Compound 7)

[0212]

[0213] Example 8 Synthesis of 2-(3,3-dimethylbutyl)-8-octylanthra[1,2-b:5,6-b']dithiophene (Compound 8) The same procedure as in Example 4 was repeated, except that octylboronic acid (Tokyo Chemical Industry Co., Ltd.) was used instead of propylboronic acid, to obtain 22.0 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-octylanthra[1,2-b:5,6-b']dithiophene (Compound 8) (yield: 32%).

[0214] １ H NMR (CDCl ３ ​​): δ = 8.58 (s, 2H), 7.84 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.69 (d, J = 8.8Hz, 1H), 7.16 (s, 1H), 7.1 5 (s, 1H), 3.02-2.96 (m, 4H), 1.87-1.74 (m, 4H), 1.49-1.29 (m, 10H), 1.03 (s, 9H), 0.89 (t, J = 7.2Hz, 3H).

[0215] Melting point: 132°C (Compound 8)

[0216]

[0217] Synthesis Example 2: Synthesis of 2-(4-pentylphenethyl)ethan-1-ol Under a nitrogen atmosphere, 5.02 g (22.1 mmol) of 1-bromo-4-pentylbenzene (Tokyo Chemical Industry Co., Ltd.) and 80 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 300 mL Schlenk reaction vessel. The mixture was cooled to -78°C, and 20.0 mL (32.0 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, followed by stirring at -78°C for 1.5 hours. To this solution, 25.0 mL (30.0 mmol) of 1.2 M ethylene oxide THF solution (Tokyo Chemical Industry Co., Ltd.) was added at -78°C, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added to the mixture at 0°C, followed by the addition of toluene to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: dichloromethane, ethyl acetate) to obtain 1.84 g of colorless liquid 2-(4-pentylphenethyl)ethan-1-ol (yield: 42%).

[0218] １ H NMR (CDCl ３ ): δ = 7.12 (s, 4H), 3.83 (t, J = 6.6 Hz, 2H), 2.83 (t, J = 6.5 Hz, 2H), 2.57 (t, J = 7.6 Hz, 2H), 1.64-1.56 (m, 2H), 1.50 (brs, 1H), 1.36-1.30 (m, 4H), 0.89 (t, J = 6.9 Hz, 3H). (2-(4-Pentylphenethyl)ethan-1-ol)

[0219]

[0220] ​Synthesis Example 3: Synthesis of 1-(2-bromoethyl)-4-pentylbenzene Under a nitrogen atmosphere, 2.27 g (11.8 mmol) of 2-(4-pentylphenethyl)ethan-1-ol synthesized in Synthesis Example 2 and 20 ml of toluene (Fujifilm Wako Pure Chemical Industries, dehydrated grade) were placed in a 100 ml three-neck flask. 0.560 ml (5.90 mmol) of phosphorus tribromide (Fujifilm Wako Pure Chemical Industries) was added to this solution at room temperature and stirred for 10 minutes, followed by stirring at 100°C for 3 hours. The reaction solution was poured onto ice, neutralized with saturated aqueous sodium bicarbonate, and then toluene was added to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: dichloromethane) to obtain 2.51 g of 1-(2-bromoethyl)-4-pentylbenzene as a colorless liquid (yield: 81%).

[0221] １ H NMR (CDCl ３ ): δ = 7.15-7.11 (m, 4H), 3.56 (t, J = 7.4 Hz, 2H), 3.14 (t, J = 7.9 Hz, 2H), 2.59 (t, J = 7.7 Hz, 2H), 1.65-1.56 (m, 2H), 1.37-1.31 (m, 4H), 0.90 (t, J = 6.8 Hz, 3H). (1-(2-Bromoethyl)-4-pentylbenzene)

[0222]

[0223] ​Synthesis Example 4 Synthesis of 4,4,5,5-tetramethyl-2-(4-pentylphenethyl)-1,3,2-dioxaborolane Under a nitrogen atmosphere, 124 mg (0.214 mmol) of Xantphos (Tokyo Chemical Industry Co., Ltd.), 1.22 g (4.79 mmol) of bis(pinacolato)diboron (Tokyo Chemical Industry Co., Ltd.), 21.0 mg (0.21 mmol) of copper(I) chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), 533 mg (4.75 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 8 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were placed in a 50 ml Schlenk reaction vessel and stirred at room temperature for 25 minutes. Under ice cooling, 2.0 mL of a THF solution (Fujifilm Wako Pure Chemical Industries, dehydrated grade) of 1.00 g (3.92 mmol) of 1-(2-bromoethyl)-4-pentylbenzene synthesized in Synthesis Example 3 was added, and the mixture was stirred at 0°C for 25 minutes and at room temperature for 3 hours. The reaction mixture was ice cooled, and water and then toluene were added to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene) to obtain 908 mg of 4,4,5,5-tetramethyl-2-(4-pentylphenethyl)-1,3,2-dioxaborolane as a colorless liquid (yield: 74%). 1H- １ H NMR (CDCl ３ ): δ = 7.12 (d, J = 8.2 Hz, 2H), 7.07 (d, J = 7.8 Hz, 2H), 2.71 (t, J = 8.2 Hz, 2H), 2.55 (t, J = 7.8 Hz, 2H), 1.63-1.55 (m, 2H), 1.37-1.28 (m, 4H), 1.22 (s, 12H), 1.13 (t, J = 8.2 Hz, 2H), 0.88 (t, J = 7.1 Hz, 3H). (4,4,5,5-tetramethyl-2-(4-pentylphenethyl)-1,3,2-dioxaborolane)

[0224]

[0225] Example 9 Synthesis of 2-(3,3-dimethylbutyl)-8-(4-pentylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 9) The same procedure as in Example 4 was repeated, except that 4,4,5,5-tetramethyl-2-(4-pentylphenethyl)-1,3,2-dioxaborolane synthesized in Synthesis Example 4 was used instead of propylboronic acid in Example 4, to obtain 12.9 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-(4-pentylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 9) (yield: 26%).

[0226] １ H NMR (CDCl ３ ): δ = 8.59 (s, 2H), 7.84 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.69 (d, J=8.8Hz, 1H), 7.19-7.12 (m, 6H), 3.31 (t, J=7.8Hz, 2H), 3.11 (t, J = 8.0Hz, 2H), 3.01-2.96 (m, 2H), 2.59 (t, J = 7.8Hz, 2H), 1.79-1.74 (m, 2H), 1.61 (t, J = 7.3Hz, 2H), 1.35-1.32 (m, 4H), 1.03 (s, 9H), 0.90 (t, J =7.1Hz, 3H).

[0227] Melting point: 190°C (Compound 9)

[0228]

[0229] ​Synthesis Example 5 Synthesis of 2-(4-hexylphenethyl)ethan-1-ol Under a nitrogen atmosphere, 4.93 g (20.4 mmol) of 1-bromo-4-hexylbenzene (Tokyo Chemical Industry Co., Ltd.) and 80 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 300 mL Schlenk reaction vessel. The mixture was cooled to -78°C, and 22.0 mL (35.2 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, followed by stirring at -78°C for 3.0 hours. To this solution, 25.0 mL (30.0 mmol) of 1.2 M ethylene oxide THF solution (Tokyo Chemical Industry Co., Ltd.) was added at -78°C, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added to the mixture at 0°C, followed by the addition of toluene to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: dichloromethane, ethyl acetate) to obtain 2.87 g of 2-(4-hexylphenethyl)ethan-1-ol as a colorless liquid (yield: 66%).

[0230] １ H NMR (CDCl ３ ): δ = 7.13 (s, 4H), 3.87-3.83 (m, 2H), 2.84 (t, J = 6.4 Hz, 2H), 2.58 (t, J = 7.8 Hz, 2H), 1.63-1.56 (m, 2H), 1.37-1.24 (m, 7H), 0.88 (t, J = 6.9 Hz, 3H). (2-(4-Hexylphenethyl)ethan-1-ol)

[0231]

[0232] ​Synthesis Example 6: Synthesis of 1-(2-bromoethyl)-4-hexylbenzene Under a nitrogen atmosphere, 2.87 g (13.9 mmol) of 2-(4-hexylphenethyl)ethan-1-ol synthesized in Synthesis Example 5 and 20 ml of toluene (Fujifilm Wako Pure Chemical Industries, dehydrated grade) were placed in a 100 ml three-neck flask. 0.670 ml (7.05 mmol) of phosphorus tribromide (Fujifilm Wako Pure Chemical Industries) was added to this solution at room temperature and stirred for 30 minutes, followed by stirring at 100°C for 3 hours and 20 minutes. The reaction solution was poured onto ice, neutralized with a saturated aqueous solution of sodium bicarbonate, and then toluene was added to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 433 mg of 1-(2-bromoethyl)-4-hexylbenzene as a colorless liquid (yield: 12%).

[0233] １ H NMR (CDCl ３ ): δ = 7.16-7.09 (m, 4H), 3.55 (t, J = 7.8 Hz, 2H), 3.13 (t, J = 7.8 Hz, 2H), 2.58 (t, J = 7.8 Hz, 2H), 1.63-1.55 (m, 2H), 1.38-1.25 (m, 6H), 0.88 (t, J = 6.9 Hz, 3H). (1-(2-Bromoethyl)-4-pentylbenzene)

[0234]

[0235] ​Synthesis Example 7 Synthesis of 4,4,5,5-tetramethyl-2-(4-hexylphenethyl)-1,3,2-dioxaborolane Under a nitrogen atmosphere, 61.4 mg (0.106 mmol) of Xantphos (Tokyo Chemical Industry Co., Ltd.), 498 mg (1.96 mmol) of bis(pinacolato)diboron (Tokyo Chemical Industry Co., Ltd.), 10.4 mg (0.105 mmol) of copper(I) chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), 200 mg (1.8 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 3.3 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were placed in a 50 ml Schlenk reaction vessel and stirred at room temperature for 30 minutes. Under ice cooling, 1.0 mL of a THF solution (Fujifilm Wako Pure Chemical Industries, dehydrated grade) of 403 mg (1.50 mmol) of 1-(2-bromoethyl)-4-pentylbenzene synthesized in Synthesis Example 6 was added, and the mixture was stirred at 0°C for 10 minutes and then at room temperature for 3 hours and 30 minutes. The reaction mixture was ice-cooled, and water and then toluene were added to separate the phases. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene) to obtain 341 mg of a yellow liquid, 4,5,5-tetramethyl-2-(4-hexylphenethyl)-1,3,2-dioxaborolane (yield: 69%).

[0236] １ H NMR (CDCl ３ ): δ = 7.12 (d, J = 8.2 Hz, 2H), 7.07 (d, J = 7.8 Hz, 2H), 2.71 (t, J = 8.2 Hz, 2H), 2.55 (t, J = 7.8 Hz, 2H), 1.62-1.54 (m, 2H), 1.37-1.25 (m, 6H), 1.22 (s, 12H), 1.13 (t, J = 8.2 Hz, 2H), 0.88 (t, J = 6.9 Hz, 3H). (4,4,5,5-tetramethyl-2-(4-hexylphenethyl)-1,3,2-dioxaborolane)

[0237]

[0238] ​Example 10 Synthesis of 2-(3,3-dimethylbutyl)-8-(4-hexylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 10) The same procedure as in Example 4 was repeated, except that 4,4,5,5-tetramethyl-2-(4-hexylphenethyl)-1,3,2-dioxaborolane synthesized in Synthesis Example 7 was used instead of propylboronic acid in Example 4, to obtain 40.0 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-(4-hexylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 10) (yield: 56%).

[0239] １ H NMR (CDCl ３ ): δ = 8.59 (s, 2H), 7.84 (d, J = 8.7Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.69 (d , J=8.8Hz, 1H), 7.20-7.12 (m, 6H), 3.31 (t, J=8.0Hz, 2H), 3.11 (t, J=8.0 Hz, 2H), 3.01-2.96 (m, 2H), 2.59 (t, J=7.8Hz, 2H), 1.79-1.74 (m, 2H), 1. 62-1.57 (m, 2H), 1.36-1.30 (m, 6H), 1.03 (s, 9H), 0.88 (t, J=6.6Hz, 3H).

[0240] Melting point: 177°C (Compound 10)

[0241]

[0242] Synthesis Example 8 Synthesis of 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane Under a nitrogen atmosphere and ice cooling, 52.0 mL (46.8 mmol) of an 8.5% borane / THF solution (Tokyo Chemical Industry Co., Ltd.) and 5.60 mL (23 mmol) of 4-n-octylstyrene (Tokyo Chemical Industry Co., Ltd.) were added to a 100 mL two-neck flask and stirred at 0°C for 1 hour and at room temperature for 2 hours. Under ice cooling, 6.2 mL of water was added and stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure, and ethyl acetate and aqueous sodium bicarbonate solution were added to separate the phases. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to synthesize (4-octylphenylethyl)boronic acid.

[0243] ​The obtained boronic acid was placed in a 300 mL recovery flask under a nitrogen atmosphere, and 5.78 g (48.7 mmol) of pinacol (Tokyo Chemical Industry Co., Ltd.) and 40.0 mL of diethyl ether (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added and stirred at room temperature. 6.09 g (50.6 mmol) of magnesium sulfate (Fujifilm Wako Pure Chemical Industries, Ltd.) was added and stirred at room temperature for 4 hours. The solid was filtered off under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene / hexane) to obtain 2.40 g of a colorless liquid, 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane (yield: 29%).

[0244] １ H NMR (CDCl ３ ): δ = 7.12 (d, J = 8.1 Hz, 2H), 7.07 (d, J = 8.1 Hz, 2H), 2.72 (t, J = 8.1 Hz, 2H), 2.56 (t, J = 7.6 Hz, 2H), 1.62-1.55 (m, 2H), 1.34-1.26 (m, 10H), 1.23 (s, 12H), 1.14 (t, J = 8.3 Hz, 2H), 0.89 (t, J = 6.7 Hz, 3H). 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane

[0245]

[0246] Example 11 Synthesis of 2-(3,3-dimethylbutyl)-8-(4-octylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 11) The same procedure as in Example 4 was repeated, except that 4,4,5,5-tetramethyl-2-(4-octylphenethyl)-1,3,2-dioxaborolane synthesized in Synthesis Example 8 was used instead of propylboronic acid in Example 4, to obtain 31.1 mg of a yellow solid, 2-(3,3-dimethylbutyl)-8-(4-octylphenethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 11) (yield: 47%).

[0247] １ H NMR (CDCl ３ ​​): δ = 8.58 (s, 2H), 7.84 (d, J = 8.7Hz, 2H), 7.70 (d, J = 8.8Hz, 1H), 7.69 (d, J = 8.8Hz, 1H), 7.19-7.12 (m, 6H), 3.31 (t, J = 7.3Hz, 2H), 3.11 (t, J = 8.5H z, 2H), 3.01-2.97 (m, 2H), 2.59 (t, J=7.6Hz, 2H), 1.79-1.75 (m, 2H), 1.6 5-1.58 (m, 2H), 1.36-1.28 (m, 10H), 1.03 (s, 9H), 0.88 (t, J=6.4Hz, 3H).

[0248] Melting point: 166°C (Compound 11)

[0249]

[0250] Example 12 Evaluation of Solubility Toluene was added to a predetermined amount of the aromatic compound obtained in Examples 1, 4, 5, 6, 7, and 8 to obtain a film-forming composition, and the weight of each organic solvent required to completely dissolve the aromatic compound at room temperature (25°C) was measured, and the solubility (wt%) was calculated. The time when the aromatic compound was completely dissolved was determined visually. The solubilities of the evaluated aromatic compounds are shown in Table 1.

[0251]

[0252] Example 13 Preparation of Organic Semiconductor Layer-Forming Solution, Organic Semiconductor Layer, and Organic Thin Film Transistor 1 To a 10 ml sample tube under air, 1.74 mg of 2-(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (Compound 1) synthesized in Example 1 and 868 mg of toluene (Fujifilm Wako Pure Chemical Industries, Pure Grade) were added, heated to 50°C for dissolution, and then allowed to cool to room temperature (25°C) to prepare an organic semiconductor layer-forming solution. The organic semiconductor layer-forming solution maintained its solution state even after 10 hours at 25°C (Compound 1 concentration: 0.20 wt%), confirming that Compound 1 is a compound suitable for film formation by drop casting and inkjet.

[0253] Using the obtained organic semiconductor layer-forming solution, a bottom-gate-bottom-contact type p-type organic thin-film transistor was fabricated. The materials (constituent substrates) of each component and the film-forming method are shown in Table 2.

[0254]

[0255] The transfer characteristics of the transistor element were evaluated, and the carrier mobility of the holes was found to be 1.90 cm ２ / V·sec.

[0256] Example 14: Preparation 2 of an organic semiconductor layer-forming solution, an organic semiconductor layer, and an organic thin-film transistor An organic semiconductor layer-forming solution was prepared in the same manner as in Example 13, except that 2,8-di(3,3-dimethylbutyl)anthra[1,2-b:5,6-b']dithiophene (compound 2) synthesized in Example 2 was used instead of compound 1. The organic semiconductor layer-forming solution maintained its solution state even after 10 hours at 25°C (compound 2 concentration: 0.20 wt%), confirming that compound 2 is a compound suitable for film formation by drop casting and inkjet.

[0257] Using the obtained organic semiconductor layer-forming solution and the materials and film-forming method for each component shown in Example 13, a bottom gate-bottom contact type p-type organic thin film transistor was fabricated.

[0258] The transfer characteristics of the transistor element were evaluated, and the carrier mobility of the holes was found to be 1.73 cm ２ / V·sec.

[0259] Example 15: Preparation of organic semiconductor layer-forming solution, organic semiconductor layer, and organic thin-film transistor 3 An organic semiconductor layer-forming solution was prepared in the same manner as in Example 13, except that 2-(3,3-dimethylbutyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (compound 7) synthesized in Example 7 was used instead of compound 1. The organic semiconductor layer-forming solution maintained its solution state even after 10 hours at 25°C (compound 7 concentration: 0.20 wt%), confirming that compound 7 is a compound suitable for film formation by drop casting and inkjet.

[0260] Using the obtained organic semiconductor layer-forming solution and the materials and film-forming method for each component shown in Example 13, a bottom gate-bottom contact type p-type organic thin film transistor was fabricated.

[0261] The transfer characteristics of the transistor element were evaluated, and the carrier mobility of the holes was found to be 1.89 cm ２ / V·sec.

[0262] Example 16: Preparation of organic semiconductor layer-forming solution, organic semiconductor layer, and organic thin-film transistor 4 An organic semiconductor layer-forming solution was prepared in the same manner as in Example 13, except that 2-(3,3-dimethylbutyl)-8-octylanthra[1,2-b:5,6-b']dithiophene (compound 8) synthesized in Example 8 was used instead of compound 1. The organic semiconductor layer-forming solution maintained its solution state even after 10 hours at 25°C (concentration of compound 8 was 0.20 wt%), confirming that compound 8 is a compound suitable for film formation by drop casting and inkjet.

[0263] Using the obtained organic semiconductor layer-forming solution and the materials and film-forming method for each component shown in Example 13, a bottom gate-bottom contact type p-type organic thin film transistor was fabricated.

[0264] The transfer characteristics of the transistor element were evaluated, and the carrier mobility of the holes was found to be 2.18 cm ２ / V·sec.

[0265] Comparative Example 1 (Preparation of a solution for forming an organic semiconductor layer) 0.44 mg of 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophene (Sigma-Aldrich) and 434 mg of toluene (Fujifilm Wako Pure Chemical Industries, Pure Grade) were added to a 10 ml sample tube under air, heated to 50°C, and allowed to cool to room temperature (25°C), whereupon it was confirmed that a solid had precipitated. Due to its low solubility, it was confirmed that this compound is unsuitable for film formation by drop casting or inkjet.

[0266] Comparative Example 2 (Preparation of solution for forming organic semiconductor layer) Using 2,8-dioctylanthra[1,2-b:5,6-b']dithiophene synthesized by the method described in WO2021 / 177417, a solution for forming an organic semiconductor layer was prepared in a 10 ml sample tube under air in the same manner as in Example 25. The solution for forming an organic semiconductor layer maintained a solution state (0.20 wt %) even after 10 hours at 25°C, confirming that the compound is suitable for film formation by drop casting and inkjet.

[0267] (Fabrication of Organic Semiconductor Layer and Organic Thin-Film Transistor) Using the organic semiconductor layer-forming solution, an attempt was made to fabricate a bottom-gate-bottom-contact type p-type organic thin-film transistor using the materials and film-forming method for each component shown in Example 25. However, no thin film was formed, and a bottom-gate-bottom-contact type p-type organic thin-film transistor could not be fabricated.

[0268] Comparative Example 3 The solubility of 2,8-di(2-phenylethyl)anthra[1,2-b:5,6-b']dithiophene (compound 10 in the publication) synthesized by the method described in WO2021 / 177417 was evaluated in toluene by the method of Example 13. The result was less than 0.5% by weight, confirming that the solubility in toluene was inferior to that of the compound of this patent.

[0269] The aromatic compound of the present invention provides high carrier mobility and is excellent in heat resistance and solubility, and is therefore expected to be used as a material for semiconductor devices such as organic thin film transistors.

[0270] 1: Organic semiconductor layer 2: Substrate 3: Gate electrode 4: Gate insulating layer 5: Source electrode 6: Drain electrode 1001: Bottom gate-top contact organic thin film transistor 1002: Bottom gate-bottom contact organic thin film transistor 1003: Top gate-top contact organic thin film transistor 1004: Top gate-bottom contact organic thin film transistor

Claims

1. An aromatic compound represented by either the following formula (5) or the following formula (5-2): [(where R ２５ ~R ２８ Among the combinations of adjacent two of these, only one pair constitutes the following formula (6), and R ２９ ~R ３２ Among the combinations of adjacent two of R, only one pair constitutes the following formula (6-2), forming a 5-membered ring or a 6-membered ring, respectively. ２５ ~R ３２ , and R ６９ and R ７０ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the following formula (2): (wherein k and m each independently represent 0 or 1, and l represents an integer from 1 to 20.) (where X ７ is an oxygen atom, a sulfur atom, a selenium atom, CR ３４ =CR ３５ , or NR ３６ Indicates Y ４ is CR ３７ or a nitrogen atom. ３４ ~R ３７ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the formula (2), R ３３ is a group represented by the formula (2). (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｂ represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by the formula (2).

2. The aromatic compound according to claim 1, wherein the formula (6-2) is the following formula (6-3): (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｃ represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms.

3. The aromatic compound according to claim 1, wherein the formula (6-2) is the following formula (6-4): (where X ７ , Y ４ is X in the formula (6) ７ , Y ４ and R ３３ｄ is an alkylaryl group having 5 to 28 carbon atoms or a group represented by the formula (2).

4. The aromatic compound according to claim 1, wherein the aromatic compound represented by formula (5) or (5-2) is a compound represented by one selected from the group consisting of the following formulas (7-1) to (7-6): (where X ８ , X ９ are each independently an oxygen atom, a sulfur atom, a selenium atom, or NR ４４ Indicates Y ５ , Y ６ are each independently CR ４５ or a nitrogen atom. ３８ ~R ４５ , R ７１ , R ７２ each independently represents one selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkadienyl group having 4 to 22 carbon atoms, an alkadiynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, an alkylaryl group having 5 to 28 carbon atoms, and a group represented by formula (2), R ３８ and R ４１ At least one of the above is a group represented by formula (2).

5. R ３８ and R ４１ are each independently one selected from the group consisting of a group represented by formula (2), a hydrogen atom, and an alkyl group having 1 to 20 carbon atoms, and R ３９ , R ４０ , R ４２ ~R ４５ , R ７１ and R ７２ The aromatic compound according to claim 4, wherein is a hydrogen atom.

6. R ３８ and R ４１ is a group represented by the formula (2), and R ３９ , R ４０ , R ４２ ~R ４５ , R ７１ and R ７２ The aromatic compound according to claim 4, wherein is a hydrogen atom.

7. A solution for forming an organic semiconductor layer, comprising the aromatic compound according to any one of claims 1 to 6.

8. An organic semiconductor layer containing the aromatic compound according to any one of claims 1 to 6.

9. An organic thin film transistor containing the aromatic compound according to any one of claims 1 to 6.

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