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

Abstract

Provided is an aromatic compound which is a coating-type organic semiconductor material having high carrier mobility, high heat resistance, and high solubility. The aromatic compound is represented by formula (1-I) or (1-II), Ar represents a monoring or the like, X1 and X2 represent oxygen atoms or the like, Y1 and Y2 represent CR6 or the like, R1-R6 represent hydrogen atoms or the like, and at least one of R1-R6 is a group represented by formula (2). K and m represent 0 or 1, n represents an integer of 1-8, l represents an integer of 1-20, and Z1 and Z2 represent a hydrogen atom or the like. [Chemical Formula 1] # imgabs0 # [Chemical Formula 2] # imgabs1 #

Description

Technical Field

[0001] The present invention relates to a novel aromatic compound that can be developed into an electronic material such as an organic semiconductor material, an organic semiconductor layer using the aromatic compound, and an organic thin-film transistor. In particular, the present invention relates to an aromatic compound having a specific substituent that can be applied to various device manufacturing processes due to its excellent solubility and heat resistance, an organic semiconductor layer using the aromatic compound, and an organic thin-film transistor. Background Art

[0002] Organic semiconductor devices, typified by organic thin-film transistors (OTTs), have attracted significant attention in recent years due to their energy efficiency, low cost, and flexibility, characteristics not found in inorganic semiconductor devices. These devices are composed of a variety of materials, including an organic semiconductor layer, a substrate, an insulating layer, and electrodes. The organic semiconductor layer, responsible for the transport of charge carriers, plays a central role in the device. Furthermore, the performance of organic semiconductor devices is determined by the carrier mobility of the organic semiconductor materials that comprise this layer. Therefore, organic semiconductor materials offering high carrier mobility are highly desired.

[0003] Methods for producing organic semiconductor layers generally include vacuum deposition, which involves vaporizing an organic material under high-temperature vacuum conditions, and coating, which involves dissolving an organic material in a suitable solvent and applying the resulting solution. Coating, in particular, can be performed using printing techniques without requiring high-temperature, high-vacuum conditions, and thus is expected to significantly reduce device production costs, making it an economically preferred process.

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

[0005] Generally speaking, low-molecular-weight semiconductors having a rod-shaped molecular long axis of a fused ring system are known to have higher crystallinity than high-molecular-weight semiconductors and therefore tend to exhibit high carrier mobility. Currently, as low-molecular-weight materials, 2,7-dialkyl-substituted benzothienobenzothiophene (for example, see Patent Document 1 and Non-Patent Document 1), 2,7-diphenyl[1]benzothieno[3,2-b][1]benzothiophene (for example, see Non-Patent Document 2), dithienobiphenylene derivatives (for example, see Patent Document 2), etc. have been proposed. Prior art literature Patent Literature

[0006] Patent Document 1: WO2008 / 047896 Patent Document 2: WO2021 / 177417 Non-patent literature

[0007] Non-patent document 1: Journal of the American Chemical Society, 2007, Vol. 129, pp. 15732-15733 Non-patent document 2: Journal of the American Chemical Society, 2006, Vol. 128, pp. 12604-12605 Summary of the Invention Technical problem to be solved by the invention

[0008] However, low solubility of low-molecular-weight semiconductors is generally a technical problem. Therefore, although there have been reports of semiconductors that incorporate alkyl groups to improve solubility, these have resulted in reduced carrier mobility and heat resistance. Furthermore, although there have been reports of semiconductors that incorporate aromatic substituents to exhibit high carrier mobility due to π-stacking, these reports also show that this high mobility is traded for a significant decrease in solubility. Therefore, currently, little is known about low-molecular-weight organic semiconductor materials that combine high carrier mobility, high heat resistance, and high solubility.

[0009] For example, the dialkyl-substituted benzothienobenzothiophene described in Patent Document 1 and Non-Patent Document 1 has a problem in that the transistor loses its heat resistance when heated to 130° C. or higher.

[0010] 2,7-Diphenyl[1]benzothieno[3,2-b][1]benzothiophene described in Non-Patent Document 2 is generally almost insoluble in organic solvents and has technical problems in terms of solubility.

[0011] Furthermore, although the alkyl-substituted dithienobiphenyl derivatives described in Patent Document 2 have both high heat resistance and moderate solubility and are suitable for use in organic semiconductors, compounds with even higher solubility are desired in order to cope with a wide range of device manufacturing processes.

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

[0013] The present inventors conducted intensive research to solve the above-mentioned technical problems and found that a novel aromatic compound having specific substituents can provide an organic semiconductor material having high carrier mobility, high heat resistance and high solubility, thereby completing the present invention.

[0014] Specifically, the present invention relates to an aromatic compound represented by any one of the following formulas (1-I) or (1-II), an organic semiconductor layer containing the aromatic compound, and an organic thin-film transistor including the organic semiconductor layer.

[0015] [Chemical Formula 1] [(wherein, Ar represents a single ring or 2 to 6 condensed rings. X 1 、X 2 Each independently represents a member selected from oxygen, sulfur, selenium, NR 3 and CR 4 =CR 5 One of the groups. 1 、Y 2 Each independently represents CR 6 or nitrogen atoms. 1 ~R 6 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), R 1 ~R 6 At least one of them is a group represented by the following formula (2).

[0016] [Chemical Formula 2] (wherein, k and m each independently represent 0 or 1, n represents an integer from 1 to 8, and l represents an integer from 1 to 20. 1 ~Z 5 is the same or different at each occurrence and represents one selected from the group consisting of a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms. Effects of the Invention

[0017] The novel aromatic compound of the present invention has high heat resistance and high solubility while providing high carrier mobility, and thus can provide an organic thin film transistor exhibiting excellent semiconductor properties upon coating. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 A diagram showing the structure of an organic thin film transistor based on a cross-sectional shape. DETAILED DESCRIPTION

[0019] Hereinafter, the present invention will be described in detail.

[0020] 〔1. Aromatic compounds〕 The present invention is an aromatic compound represented by any one of the above formulas (1-I) and (1-II) (hereinafter referred to as "the compound of the present invention").

[0021] Ar in formula (1-I) and formula (1-II) represents a monocyclic ring or 2 to 6 fused rings. From the viewpoint of providing higher carrier mobility in the compound of the present invention, Ar is preferably 2 to 4 fused rings. Furthermore, in order to make the compound of the present invention exhibit higher solubility, Ar is more preferably 2 to 3 fused rings.

[0022] The monocyclic ring or each ring constituting the 2 to 6 condensed rings is a 4- to 8-membered ring, and preferably a 4- to 6-membered ring from the viewpoint of facilitating π-stacking of the compound of the present invention.

[0023] Specific examples of the monocyclic ring or 2 to 6 condensed rings represented by Ar include monocyclic rings such as a cyclobutene ring, a thiophene ring, a furan ring, a selenophene ring, a thiazole ring, an oxazole ring, a pyrrole ring, an imidazole ring, a benzene ring, and a pyridine ring; and condensed rings such as a thienothiophene ring, a naphthalene ring, a biphenylene ring, an anthracene ring, a dithienothiophene ring, a dithienobenzo ring, a benzothienobenzothiophene ring, a tetracene ring, a bis(dithieno)benzo ring, and a bis(benzothiophene)benzo ring. In order to provide the compound of the present invention with higher carrier mobility, 2 to 4 condensed rings of a thienothiophene ring, a naphthalene ring, a biphenylene ring, an anthracene ring, a dithienothiophene ring, and a benzothienobenzothiophene ring are preferred, and 2 to 3 condensed rings of a thienothiophene ring, a naphthalene ring, a biphenylene ring, and an anthracene ring are more preferred.

[0024] X in formula (1-I) and formula (1-II) 1 、X 2 Each independently represents a member selected from oxygen, sulfur, selenium, NR 3 and CR 4 =CR 5 In order to make the compound of the present invention show higher stability, X 1 and X 2 At least one of them is preferably a sulfur atom or CR 4 =CR 5 More preferably, both of them are sulfur atoms.

[0025] Y in formula (1-I) and formula (1-II) 1 、Y 2 Each independently represents CR 6 In order to make the compound of the present invention show higher stability, Y 1 and Y 2 At least one of the above is preferably CR 6 .

[0026] R in formula (1-I) and formula (1-II) 1 ~R 6 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), and R 1 ~R 6 At least one of them is a group represented by formula (2).

[0027] As the R 1 ~R 6 The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and is preferably a fluorine atom or a chlorine atom from the viewpoint of stability of the compound of the present invention.

[0028] As the R 1 ~R 6 The alkyl group having 1 to 20 carbon atoms in the alkyl group includes, for example, a linear, branched, or cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an isovaleryl group, an n-hexyl group, an isohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-octadecyl group, a 2-ethylhexyl group, a 3-ethylheptyl group, a 3-ethyldecyl group, a 2-hexyldecyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Among these, from the viewpoint that the compound of the present invention provides an aromatic compound with higher carrier mobility and higher solubility, an alkyl group having 1 to 14 carbon atoms is preferred, and a linear alkyl group having 1 to 14 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-dodecyl group, an n-tridecyl group, and an n-tetradecyl group is more preferred.

[0029] As the R 1 ~R 6Examples of the alkenyl group having 2 to 20 carbon atoms 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, cyclopenten-1-yl, cyclohexen-1-yl, and cyclohepten-1-yl.

[0030] As the R 1 ~R 6 Examples of the alkynyl group having 2 to 20 carbon atoms include ethynyl, propynyl, butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl, and n-dodecynyl.

[0031] As the R 1 ~R 6 The dienyl group having 4 to 22 carbon atoms in the group includes, for example, butadienyl, pentadienyl, hexadienyl, n-heptadienyl, n-octadienyl, n-nonadienyl, n-decadienyl, n-dodecadienyl, and n-tridecadienyl. 1,3-dienyl groups having 4 to 22 carbon atoms are preferred, and hexa-1,3-dienyl, n-heptadienyl, n-octadienyl, n-non-1,3-dienyl, and n-decadienyl are more preferred.

[0032] As the R 1 ~R 6 The dialkynyl group having 4 to 22 carbon atoms in the group includes, for example, butadiynyl, pentadiynyl, hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, n-decadiynyl, n-dodecadiynyl, and n-tridecadiynyl. 1,3-diynyl having 4 to 22 carbon atoms is preferred, and hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, and n-decadiynyl are more preferred.

[0033] The R 1 ~R 6The aryl group having 4 to 26 carbon atoms in the aryl group includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include phenyl; alkyl-substituted phenyl groups such as p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl; 2-furyl, 2-thienyl; 5-fluoro-2-furyl, 5-methyl-2-furyl, 5-ethyl-2-furyl, 5-(n-propyl)-2-furyl, 5-(n-butyl)-2-furyl, 5-(n-pentyl)-2-furyl, 5-(n-hexyl)-2- Alkyl-substituted heteroaryl groups include furyl, 5-(n-octyl)-2-furyl, 5-(2-ethylhexyl)-2-furyl, 5-fluoro-2-thienyl, 5-methyl-2-thienyl, 5-ethyl-2-thienyl, 5-(n-propyl)-2-thienyl, 5-(n-butyl)-2-thienyl, 5-(n-pentyl)-2-thienyl, 5-(n-hexyl)-2-thienyl, 5-(n-octyl)-2-thienyl, and 5-(2-ethylhexyl)-2-thienyl. In this specification, when an aryl group includes an alkyl substitution, an aryl group having 4 to 26 carbon atoms means "having 4 to 26 carbon atoms" including the carbon atoms of the alkyl portion.

[0034] In formula (2), k and m each independently represent 0 or 1. From the perspective of ease of synthesis of the compound of the present invention, k is preferably 0. Furthermore, in order to provide the compound of the present invention with higher carrier mobility, both k and m are more preferably 0.

[0035] In formula (2), n represents 1 to 8. From the perspective of the stability of the compound of the present invention, n is preferably 3 to 6. Furthermore, in order to provide the compound of the present invention with higher carrier mobility, n is more preferably 3 to 4.

[0036] In formula (2), l represents an integer of 1 to 20. In order to make the compound of the present invention exhibit higher solubility, l is preferably an integer of 1 to 3. Furthermore, in order to make the compound of the present invention exhibit higher heat resistance, l is more preferably an integer of 1 to 2. Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, l is even more preferably 2.

[0037] Z in formula (2) 1 ~Z 5 Each occurrence of "" is the same or different and represents one selected from the group consisting of a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms.

[0038] As the Z 1 ~Z 5 The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability of the compound of the present invention, a fluorine atom or a chlorine atom is preferred.

[0039] As the Z 1 ~Z 5 The alkyl group having 1 to 20 carbon atoms in the alkyl group includes, for example, a linear, branched, or cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an isovaleryl group, an n-hexyl group, an isohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-octadecyl group, a 2-ethylhexyl group, a 3-ethylheptyl group, a 3-ethyldecyl group, a 2-hexyldecyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Among these, an alkyl group having 1 to 8 carbon atoms is preferred, and a methyl group, an ethyl group, and an n-propyl group are more preferred, because the compound of the present invention is an aromatic compound that provides higher carrier mobility and exhibits higher solubility.

[0040] In order to make the compound of the present invention a compound that provides higher carrier mobility, the Z 1 ~Z 5 It is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.

[0041] In formula (2), preferably, k and m are both 0, n is an integer of 3 to 4, l is an integer of 1 to 3, and Z 1 ~Z 5 is any one of a hydrogen atom and a halogen atom. Thus, the compound of the present invention exhibits higher carrier mobility.

[0042] In order to make the compound of the present invention a compound that provides higher carrier mobility, the group represented by formula (2) is preferably a cyclohexylmethyl group, a 2-cyclohexylethyl group, a 3-cyclohexylpropyl group, a cyclopentylmethyl group, a 2-cyclopentylethyl group, or a 3-cyclopentylpropyl group. Furthermore, in order to make the compound of the present invention exhibit higher heat resistance and higher solubility, 2-cyclohexylethyl group and 2-cyclopentylethyl group are more preferred.

[0043] In these R 1 ~R 6 For the stability of the compound of the present invention, R 1 ~R 6 Preferably, it is 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). 1 ~R 6 More preferably, it is any one of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2). Furthermore, from the viewpoint of providing a higher carrier mobility in the compound of the present invention, it is more preferable that only R1 and R 2 Either or only R 1 and R 2 Both represent groups represented by formula (2), R 3 ~R 6 A hydrogen atom.

[0044] From the perspective of ease of synthesis, the aromatic compound of formula (1-I) or (1-II) is preferably an aromatic compound represented by one selected from the group consisting of the following formulae (3-1) to (3-6).

[0045] [Chemical Formula 3] [(where X 3 、X 4 、X 5 Each independently represents a group selected from oxygen atom, sulfur atom, selenium atom, single bond, NR 17 and CR 18 =CR 19 One of the groups composed of R 7 ~R 10 Among the combinations of two adjacent components in , only one group constitutes the following formula (4), and in the combination of R 11 ~R 14 Of the two adjacent combinations in , only one group constitutes the following formula (4-2) and forms a 5-membered ring or a 6-membered ring. 7 ~R 14 and R 15 ~R 19 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by the aforementioned formula (2).

[0046] [Chemical Formula 4] (where X 6 represents an atom selected from oxygen, sulfur, selenium, CR 21 =CR 22 and NR 23 One of the groups. 3 Indicates CR 24 or nitrogen atoms. 21 ~R 24Each 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the aforementioned formula (2), and R 20 is a group represented by the aforementioned formula (2).

[0047] [Chemical Formula 5] (where X 6 、Y 3 represents X in the above formula (4) 6 、Y 3 Same meaning, R 20b 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the aforementioned formula (2). In formulas (3-1) to (3-6), 7 ~R 10 Among the combinations of two adjacent components in , only one group constitutes the above formula (4), and in the combination of R 11 ~R 14 Among the combinations of two adjacent components in , only one group constitutes the above formula (4-2) and each forms a 5-membered ring or a 6-membered ring.

[0048] R that does not form formula (4) and formula (4-2) 7 ~R 14 、R 15 ~R 19 , R in formula (4) and formula (4-2) 21 ~R 24 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2).

[0049] R 20 It is a group represented by formula (2).

[0050] R 20bis a group 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, a dienyl group having 4 to 22 carbon atoms, a dienyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2). In order to provide a compound having a higher carrier mobility, R 20b It is preferably one selected from the group consisting of a hydrogen atom, a fluorine atom and a group represented by formula (2).

[0051] Among the compounds represented by one selected from the group consisting of formulae (3-1) to (3-6), formula (4-2) is preferably the following formula (4-3).

[0052] [Chemical Formula 6] (where X 6 、Y 3 represents X in the above formula (4) 6 、Y 3 Same meaning, R 20c 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. R 20c is 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. In order to provide a higher carrier mobility for the compound of the present invention, R 20c It is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.

[0053] Among the compounds represented by one selected from the group consisting of formulae (3-1) to (3-6), formula (4-2) is preferably the following formula (4-4).

[0054] [Chemical Formula 7] (where X 6 、Y 3 represents X in the above formula (4) 6 、Y 3 Same meaning, R 20d is a group represented by the aforementioned formula (2). The definition of the group represented by formula (2) in formulas (3-1) to (3-6) is the same as the definition of formula (2) in the aforementioned formulas (1-I) and (1-II).

[0055] As the R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20c The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability of the compound of the present invention, a fluorine atom or a chlorine atom is preferred.

[0056] As the R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20c The alkyl group having 1 to 20 carbon atoms in the alkyl group includes, for example, a linear, branched, or cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an isovaleryl group, an n-hexyl group, an isohexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-octadecyl group, a 2-ethylhexyl group, a 3-ethylheptyl group, a 3-ethyldecyl group, a 2-hexyldecyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Among these, an alkyl group having 1 to 14 carbon atoms is preferred, and a linear alkyl group having 1 to 14 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-dodecyl group, an n-tridecyl group, and an n-tetradecyl group is more preferred, because the compound of the present invention becomes an aromatic compound that provides higher carrier mobility and exhibits higher solubility.

[0057] As the R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20c The alkenyl group having 2 to 20 carbon atoms in the group includes, for example, 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, cyclopenten-1-yl, cyclohexen-1-yl, and cyclohepten-1-yl.

[0058] As the R 7 ~R 19 、R 21 ~R 24 、R20b 、R 20c Examples of the alkynyl group having 2 to 20 carbon atoms include ethynyl, propynyl, butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl, and n-dodecynyl.

[0059] As the R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20c The dienyl group having 4 to 22 carbon atoms in the group includes, for example, butadienyl, pentadienyl, hexadienyl, n-heptadienyl, n-octadienyl, n-nonadienyl, n-decadienyl, n-dodecadienyl, and n-tridecadienyl. 1,3-dienyl groups having 4 to 22 carbon atoms are preferred, and hexa-1,3-dienyl, n-heptadienyl, n-octadienyl, n-non-1,3-dienyl, and n-decadienyl are more preferred.

[0060] As the R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20c The dialkynyl group having 4 to 22 carbon atoms in the group includes, for example, butadiynyl, pentadiynyl, hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, n-decadiynyl, n-dodecadiynyl, and n-tridecadiynyl. 1,3-diynyl having 4 to 22 carbon atoms is preferred, and hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, and n-decadiynyl are more preferred.

[0061] The R 7 ~R 19 、R 21 ~R 24 、R 20b 、R 20cThe aryl group having 4 to 26 carbon atoms in the aryl group includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include phenyl; alkyl-substituted phenyl groups such as p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl; 2-furyl, 2-thienyl; 5-fluoro-2-furyl, 5-methyl-2-furyl, 5-ethyl-2-furyl, 5-(n-propyl)-2-furyl, 5-(n-butyl)-2-furyl, 5-(n-pentyl)-2-furyl, 5-(n-hexyl)-2- Alkyl-substituted heteroaryl groups include furyl, 5-(n-octyl)-2-furyl, 5-(2-ethylhexyl)-2-furyl, 5-fluoro-2-thienyl, 5-methyl-2-thienyl, 5-ethyl-2-thienyl, 5-(n-propyl)-2-thienyl, 5-(n-butyl)-2-thienyl, 5-(n-pentyl)-2-thienyl, 5-(n-hexyl)-2-thienyl, 5-(n-octyl)-2-thienyl, and 5-(2-ethylhexyl)-2-thienyl.

[0062] For the stability of the compound of the present invention, the R 7 ~R 19 It 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 make the compound of the present invention exhibit higher solubility, a hydrogen atom or an alkyl group having 1 to 20 carbon atoms is more preferable.

[0063] For the stability of the compound of the present invention, the R 21 ~R 24 Preferably, it is 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). Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, R 21 ~R 24 More preferably, it is one selected from the group consisting of a hydrogen atom and a methyl group, and even more preferably, it is a hydrogen atom.

[0064] X in formulas (3-1) to (3-6) 3 、X 4 、X 5 represents a group selected from oxygen atom, sulfur atom, selenium atom, single bond, NR 17 and CR 18 =CR 19 In order to make the compound of the present invention a compound that provides higher carrier mobility, it is preferably a sulfur atom, a single bond or CR18 =CR 19 Any one of, more preferably a sulfur atom or CR 18 =CR 19 , more preferably a sulfur atom.

[0065] X in formula (4) and (4-2) to (4-3) 6 represents an atom selected from oxygen, sulfur, selenium, CR 21 =CR 22 and NR 23 In order to make the compound of the present invention a compound that provides higher carrier mobility, it is preferably a sulfur atom or CR 21 =CR 22 , more preferably a sulfur atom.

[0066] Y in formula (4) and (4-2) to (4-3) 3 Indicates CR 24 For the stability of the compound of the present invention, CR 24 .

[0067] In order to make the compound of the present invention provide a compound with higher carrier mobility, the aromatic compounds represented by formulae (3-1) to (3-6) preferably have a point-symmetric or axisymmetric structure, and more preferably a point-symmetric structure.

[0068] The aromatic compounds represented by formulae (3-1) to (3-6) are preferably those represented by formula (3-1) or (3-2) in order to allow the compound of the present invention to exhibit higher solubility and higher heat resistance.

[0069] Furthermore, the aromatic compound represented by Formula (1-I) or Formula (1-II) is preferably an aromatic compound represented by the following Formula (5) or Formula (5-2).

[0070] [Chemical Formula 8] [(Among them, in 25 ~R 28 Among the combinations of two adjacent components in , only one group constitutes the following formula (6), and in the combination of R 29 ~R 32 Of the two adjacent combinations in , only one group constitutes the following formula (6-2) and forms a 5-membered ring or a 6-membered ring. 25 ~R 32 and R 69 、R 70Each 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by the aforementioned formula (2).

[0071] [Chemical Formula 9] (where X 7 represents oxygen atoms, sulfur atoms, selenium atoms, CR 34 =CR 35 , or NR 36 .Y 4 Indicates CR 37 or nitrogen atoms. 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the aforementioned formula (2), and R 33 is a group represented by the aforementioned formula (2).

[0072] [Chemical Formula 10] (where X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by the aforementioned formula (2). In formula (5) and (5-2), R 25 ~R 28 Among the combinations of two adjacent components in , only one group constitutes the above formula (6), and in the combination of R 29 ~R 32 Among the combinations of two adjacent components in , only one group constitutes the above formula (6-2), and each forms a 5-membered ring or a 6-membered ring.

[0073] R that does not form formula (6) and 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2).

[0074] R 33 It is a group represented by formula (2).

[0075] R 33b It 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2). From the perspective of making the compound of the present invention a compound that provides higher carrier mobility, it is preferably one selected from the group consisting of a hydrogen atom, a fluorine atom, and a group represented by formula (2).

[0076] Among the aromatic compounds represented by formula (5) or formula (5-2), formula (6-2) is preferably the following formula (6-3).

[0077] [Chemical Formula 11] (where X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. R 33c It is 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms. From the perspective of providing higher carrier mobility for the compound of the present invention, it is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.

[0078] Among the aromatic compounds represented by formula (5) or formula (5-2), formula (6-2) is also preferably the following formula (6-4).

[0079] [Chemical Formula 12] (where X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, R 33d is a group represented by the aforementioned formula (2). The definitions of the groups represented by formula (2) in formula (5) and formula (5-2) are the same as those of formula (2) in the aforementioned formula (1-I) and formula (1-II).

[0080] As the R 25 ~R 32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33c The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability of the compound of the present invention, a fluorine atom or a chlorine atom is preferred.

[0081] As the R 25 ~R 32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33c The alkyl group having 1 to 20 carbon atoms in the alkyl group includes, for example, a linear, branched, or cyclic alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isovaleryl, 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. Furthermore, from the viewpoint of providing higher carrier mobility and exhibiting higher solubility, the alkyl group is preferably an alkyl group having 1 to 14 carbon atoms, and more preferably a linear alkyl group having 1 to 14 carbon atoms such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tridecyl, and n-tetradecyl.

[0082] As the R 25 ~R32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33c The alkenyl group having 2 to 20 carbon atoms in the group includes, for example, 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-yl, cyclohexenyl-1-yl, and cycloheptenyl-1-yl.

[0083] As 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 ethynyl, propynyl, butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl, and n-dodecynyl.

[0084] As the R 25 ~R 32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33c The dienyl group having 4 to 22 carbon atoms in the group includes, for example, butadienyl, pentadienyl, hexadienyl, n-heptadienyl, n-octadienyl, n-nonadienyl, n-decadienyl, n-dodecadienyl, and n-tridecadienyl. 1,3-dienyl groups having 4 to 22 carbon atoms are preferred, and hexa-1,3-dienyl, n-heptadienyl, n-octadienyl, n-non-1,3-dienyl, and n-decadienyl are more preferred.

[0085] As the R 25 ~R 32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33cThe dialkynyl group having 4 to 22 carbon atoms in the group includes, for example, butadiynyl, pentadiynyl, hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, n-decadiynyl, n-dodecadiynyl, and n-tridecadiynyl. 1,3-diynyl having 4 to 22 carbon atoms is preferred, and hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, and n-decadiynyl are more preferred.

[0086] In the R 25 ~R 32 、R 34 ~R 37 、R 69 、R 70 、R 33b 、R 33c The aryl group having 4 to 26 carbon atoms in the aryl group includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include phenyl; alkyl-substituted phenyl groups such as p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl; 2-furyl, 2-thienyl; 5-fluoro-2-furyl, 5-methyl-2-furyl, 5-ethyl-2-furyl, 5-(n-propyl)-2-furyl, 5-(n-butyl)-2-furyl, 5-(n-pentyl)-2-furyl, 5-(n-hexyl)-2- Alkyl-substituted heteroaryl groups include furyl, 5-(n-octyl)-2-furyl, 5-(2-ethylhexyl)-2-furyl, 5-fluoro-2-thienyl, 5-methyl-2-thienyl, 5-ethyl-2-thienyl, 5-(n-propyl)-2-thienyl, 5-(n-butyl)-2-thienyl, 5-(n-pentyl)-2-thienyl, 5-(n-hexyl)-2-thienyl, 5-(n-octyl)-2-thienyl, and 5-(2-ethylhexyl)-2-thienyl.

[0087] For the stability of the compound of the present invention, the R 25 ~R 32 、R 69 、R 70 It 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 make the compound of the present invention exhibit higher solubility, it is more preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and further preferably one selected from the group consisting of a hydrogen atom and a methyl group.

[0088] For the stability of the compound of the present invention, the R 34 ~R 37Preferably, it is 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). Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, the R 34 ~R 37 More preferably, it is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2), and R 34 ~R 37 A hydrogen atom is more preferred.

[0089] X in formula (6) and (6-2) to (6-4) 7 represents oxygen atoms, sulfur atoms, selenium atoms, CR 34 =CR 35 , or NR 36 , in order to make the compound of the present invention show higher solubility, preferably a sulfur atom, an oxygen atom, a sulfur atom, a selenium atom. Furthermore, in order to make the compound of the present invention become a compound providing higher carrier mobility, X 7 More preferably, it is a sulfur atom.

[0090] Y in formula (6) and (6-2) to (6-4) 4 Indicates CR 37 or nitrogen atoms, preferably CR 37 .

[0091] In order to make the compound of the present invention provide a compound with higher carrier mobility, the aromatic compound represented by formula (5) and formula (5-2) preferably has a point-symmetric or axisymmetric structure, and more preferably has a point-symmetric structure.

[0092] In order to make the compound of the present invention exhibit higher solubility, the aromatic compound represented by formula (5) and formula (5-2) is preferably the aromatic compound represented by formula (5).

[0093] In addition, the aromatic compound represented by formula (5) or formula (5-2) is preferably a compound selected from the group consisting of the following formulas (7-1) to (7-6) from the perspective of ease of synthesis, and is particularly preferably a compound represented by (7-5).

[0094] [Chemical Formula 13] (where X 8 、X 9 Each independently represents a member selected from an oxygen atom, a sulfur atom, a selenium atom and NR 44 One of the groups.5 、Y 6 Each independently represents CR 45 or nitrogen atoms. 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), and R 38 and R 41 At least one of them is a group represented by formula (2). X in formulas (7-1) to (7-6) 8 、X 9 Each independently represents a member selected from an oxygen atom, a sulfur atom, a selenium atom and NR 44 For the stability of the compound of the present invention, preferably a sulfur atom, an oxygen atom, a sulfur atom, a selenium atom. Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, X 8 、X 9 More preferably, it is a sulfur atom.

[0095] Y in formulas (7-1) to (7-6) 5 、Y 6 Each independently represents CR 45 For the stability of the compound of the present invention, CR 45 .

[0096] 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by the above formula (2), and R 38 ~R 45 At least one of them is a group represented by the above formula (2).

[0097] R in formulas (7-1) to (7-6) 38 、R 41 Only one or both of them are groups represented by formula (2).

[0098] 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 aforementioned formula (1-I) and formula (1-II).

[0099] As the R 38 ~R 45 、R 71 、R 72 The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability of the compound of the present invention, a fluorine atom or a chlorine atom is preferred.

[0100] As the R 38 ~R 45 、R 71 、R 72 The alkyl group having 1 to 20 carbon atoms in the alkyl group may be, for example, a linear, branched, or cyclic alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isovaleryl, 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. Furthermore, from the viewpoint that the compound of the present invention provides an aromatic compound with higher carrier mobility and higher solubility, the alkyl group is preferably an alkyl group having 1 to 14 carbon atoms, and more preferably a linear alkyl group having 1 to 14 carbon atoms such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tridecyl, and n-tetradecyl.

[0101] As the R 38 ~R 45 、R 71 、R 72 The alkenyl group having 2 to 20 carbon atoms in the group includes, for example, 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, cyclopenten-1-yl, cyclohexen-1-yl, and cyclohepten-1-yl.

[0102] As the R 38 ~R 45 、R 71 、R 72 Examples of the alkynyl group having 2 to 20 carbon atoms include ethynyl, propynyl, butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl, and n-dodecynyl.

[0103] As the R38 ~R 45 、R 71 、R 72 The dienyl group having 4 to 22 carbon atoms in the group includes, for example, butadienyl, pentadienyl, hexadienyl, n-heptadienyl, n-octadienyl, n-nonadienyl, n-decadienyl, n-dodecadienyl, and n-tridecadienyl. 1,3-dienyl groups having 4 to 22 carbon atoms are preferred, and hexa-1,3-dienyl, n-heptadienyl, n-octadienyl, n-non-1,3-dienyl, and n-decadienyl are more preferred.

[0104] As the R 38 ~R 45 、R 71 、R 72 The dialkynyl group having 4 to 22 carbon atoms in the group includes, for example, butadiynyl, pentadiynyl, hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, n-decadiynyl, n-dodecadiynyl, and n-tridecadiynyl. 1,3-diynyl having 4 to 22 carbon atoms is preferred, and hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, and n-decadiynyl are more preferred.

[0105] The R 38 ~R 45 、R 71 、R 72 The aryl group having 4 to 26 carbon atoms in the aryl group includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include phenyl; alkyl-substituted phenyl groups such as p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl; 2-furyl, 2-thienyl; 5-fluoro-2-furyl, 5-methyl-2-furyl, 5-ethyl-2-furyl, 5-(n-propyl)-2-furyl, 5-(n-butyl)-2-furyl, 5-(n-pentyl)-2-furyl, 5-(n-hexyl)-2- Alkyl-substituted heteroaryl groups include furyl, 5-(n-octyl)-2-furyl, 5-(2-ethylhexyl)-2-furyl, 5-fluoro-2-thienyl, 5-methyl-2-thienyl, 5-ethyl-2-thienyl, 5-(n-propyl)-2-thienyl, 5-(n-butyl)-2-thienyl, 5-(n-pentyl)-2-thienyl, 5-(n-hexyl)-2-thienyl, 5-(n-octyl)-2-thienyl, and 5-(2-ethylhexyl)-2-thienyl.

[0106] For the stability of the compound of the present invention, the R 38 ~R 45 、R 71 、R 72Preferably, it is 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). 38 ~R 45 、R 71 、R 72 It is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2). 38 、R 41 It is preferably one selected from the group consisting of a group represented by the above formula (2), a hydrogen atom and a fluorine atom, more preferably one selected from the group consisting of a group represented by the above formula (2) and a hydrogen atom, and further preferably R 38 and R 41 Both are groups represented by the above formula (2). 39 、R 40 、R 42 ~R 45 、R 71 、R 72 More preferably, it is one selected from the group consisting of a hydrogen atom and a methyl group, and even more preferably, it is a hydrogen atom.

[0107] Among formulas (7-1) to (7-6), in order to make the compound of the present invention show higher solubility, any one of formula (7-1), (7-2) or (7-5) is preferred. Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, formula (7-5) is more preferred.

[0108] A more preferred compound structure of the compound of the present invention is represented by one selected from the group consisting of the following formulae (8-1) to (8-11) in addition to the above-mentioned formulae (7-1) to (7-6). Among them, from the viewpoint of higher heat resistance and higher solubility of the compound of the present invention, an aromatic compound having 4 to 5 fused rings selected from the group consisting of (7-1) to (7-6) and (8-2) to (8-9) is preferred. Furthermore, from the viewpoint of providing higher carrier mobility for the compound of the present invention, an aromatic compound having a point-symmetrical structure selected from the group consisting of formulae (7-1) to (7-6), (8-2) to (8-3), and (8-5) to (8-8) is further preferred.

[0109] [Chemical Formula 14] (wherein, X represents an oxygen atom, a sulfur atom, a selenium atom, NR58 and CR 59 =CR 60 One of the groups consisting of. Y represents CR 61 or nitrogen atoms. 46 ~R 61 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), and R 46 ~R 61 At least one of them is a group represented by formula (2), R 46 and R 47 At least one of them is a group represented by formula (2). o represents 0 or 1. In formulas (8-1) to (8-11), X represents a group selected from oxygen, sulfur, selenium, NR 58 and CR 59 =CR 60 For the stability of the compound of the present invention, X is preferably one of the group consisting of oxygen atoms, sulfur atoms, and selenium atoms. Furthermore, in order to make the compound of the present invention a compound that provides higher carrier mobility, X is more preferably a sulfur atom.

[0110] In formulas (8-1) to (8-11), Y represents CR 61 For the stability of the compound of the present invention, CR 61 .

[0111] R in formulas (8-1) to (8-11) 46 ~R 61 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2), and R 46 ~R 61 At least one of them is a group represented by formula (2).

[0112] In addition, the definition of the group represented by formula (2) in formulas (8-1) to (8-11) has the same meaning as that of the aforementioned formula (1-I) and formula (1-II).

[0113] As the R 46 ~R 61The halogen atom in exemplifies a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability of the compound of the present invention, a fluorine atom or a chlorine atom is preferred.

[0114] As the R 46 ~R 61 The alkyl group having 1 to 20 carbon atoms in the alkyl group may be, for example, a linear, branched, or cyclic alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isovaleryl, 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. Furthermore, from the viewpoint that the compound of the present invention provides an aromatic compound with higher carrier mobility and higher solubility, the alkyl group is preferably an alkyl group having 1 to 14 carbon atoms, and more preferably a linear alkyl group having 1 to 14 carbon atoms such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tridecyl, and n-tetradecyl.

[0115] As the R 46 ~R 61 The alkenyl group having 2 to 20 carbon atoms in the group includes, for example, 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, cyclopenten-1-yl, cyclohexen-1-yl, and cyclohepten-1-yl.

[0116] As the R 46 ~R 61 Examples of the alkynyl group having 2 to 20 carbon atoms include ethynyl, propynyl, butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, n-nonynyl, n-decynyl, and n-dodecynyl.

[0117] As the R 46 ~R 61 The dienyl group having 4 to 22 carbon atoms in the group includes, for example, butadienyl, pentadienyl, hexadienyl, n-heptadienyl, n-octadienyl, n-nonadienyl, n-decadienyl, n-dodecadienyl, and n-tridecadienyl. 1,3-dienyl groups having 4 to 22 carbon atoms are preferred, and hexa-1,3-dienyl, n-heptadienyl, n-octadienyl, n-non-1,3-dienyl, and n-decadienyl are more preferred.

[0118] As the R 46 ~R 61The dialkynyl group having 4 to 22 carbon atoms in the group includes, for example, butadiynyl, pentadiynyl, hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, n-decadiynyl, n-dodecadiynyl, and n-tridecadiynyl. 1,3-diynyl having 4 to 22 carbon atoms is preferred, and hexadiynyl, n-heptadiynyl, n-octadiynyl, n-nonadiynyl, and n-decadiynyl are more preferred.

[0119] The R 46 ~R 61 The aryl group having 4 to 26 carbon atoms in the aryl group includes a heteroaryl group having 4 to 24 carbon atoms. Examples of the aryl group having 4 to 26 carbon atoms include phenyl; alkyl-substituted phenyl groups such as p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl; 2-furyl, 2-thienyl; 5-fluoro-2-furyl, 5-methyl-2-furyl, 5-ethyl-2-furyl, 5-(n-propyl)-2-furyl, 5-(n-butyl)-2-furyl, 5-(n-pentyl)-2-furyl, 5-(n-hexyl)-2- Alkyl-substituted heteroaryl groups include furyl, 5-(n-octyl)-2-furyl, 5-(2-ethylhexyl)-2-furyl, 5-fluoro-2-thienyl, 5-methyl-2-thienyl, 5-ethyl-2-thienyl, 5-(n-propyl)-2-thienyl, 5-(n-butyl)-2-thienyl, 5-(n-pentyl)-2-thienyl, 5-(n-hexyl)-2-thienyl, 5-(n-octyl)-2-thienyl, and 5-(2-ethylhexyl)-2-thienyl.

[0120] For the stability of the compound of the present invention, the R 46 ~R 61 Preferably, it is 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). 46 With R 47 It is preferably one selected from the group consisting of a group represented by formula (2), a hydrogen atom, and a fluorine atom, more preferably one selected from the group consisting of a group represented by formula (2) and a hydrogen atom, and further preferably R 46 and R 47 Both are groups represented by formula (2). 48 ~R 61 It is preferably one selected from the group consisting of a hydrogen atom and a methyl group, and more preferably a hydrogen atom.

[0121] In formulae (8-5) and (8-6), o represents 0 or 1, and preferably represents 1 in order to make the compound of the present invention a compound that provides higher carrier mobility.

[0122] The compound of the present invention can provide an aromatic compound having high heat resistance and high solubility while providing high carrier mobility. The effect is very high. In addition, in this specification, "high carrier mobility" means a carrier mobility of 0.10 cm 2 / V·sec or more, preferably 0.15cm 2 / V·sec or more, more preferably 0.20cm 2 / V·sec or more. In addition, in this specification, "high solubility" means a solubility of 0.1 wt% or more in a solvent (e.g., toluene or n-octane) at room temperature. In addition, in this specification, "high heat resistance" means a melting point of 130°C or more.

[0123] Specific examples of the compound of the present invention include the following compounds. [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36] [Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[0124] [Chemical Formula 46] Preferred examples of these compounds include the following compounds. [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]

[0125] [Chemical Formula 51] Among these, particularly preferred compounds include the following compounds. [Chemical Formula 52]

[0126] [Chemical Formula 53] As a method for producing the compound of the present invention, any production method can be used as long as the compound can be produced.

[0127] As an example of the method for producing the aromatic compound of the present invention, for example, X of formula (7-5) 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 is a group represented by formula (2), R 39 、R 40 、R 41 、R 42 、R 43 、R 71 、R 72 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5 The aromatic compound (7-5a) containing a hydrogen atom can be produced by a method comprising the following steps A1 or B1 and C1.

[0128] (Step A1): A step of producing a borate ester by reacting an alkyl bromide derivative with bis(pinacolato)diboron in the presence of a copper catalyst and a ligand.

[0129] (Step B1): A step of reacting an olefin with borane and water to produce boric acid, and reacting the resulting boric acid with pinacol to produce a boric acid ester.

[0130] (Step C1): A step of producing an aromatic compound (7-5a) by reacting the boric 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.

[0131] The details of each step are shown below.

[0132] (A1 process) This step A1 is a step of producing a borate ester by reacting an alkyl bromide derivative with bis(pinacolato)diboron in the presence of a copper catalyst and a ligand.

[0133] Examples of the copper catalyst in this case include copper (I) iodide, copper (I) bromide, and copper (I) chloride. The copper catalyst may have a ligand, and examples of the ligand include Xantphos, Ruphos, and Xphos.

[0134] Examples of the alkyl bromide derivative in step A1 include (2-bromoethyl)cyclohexane, (3-bromopropyl)cyclohexane, (2-bromoethyl)cyclopentane, and (3-bromopropyl)cyclopentane.

[0135] (B1 process) This step B1 is a step of producing a boric acid ester by reacting an olefin with borane and water to produce boric acid, and then reacting the boric acid with pinacol.

[0136] The conditions for preparing the boronic acid include, for example, using 1 to 3 equivalents of borane in a solvent such as THF or diethyl ether at a temperature ranging from 0°C to 40°C.

[0137] In addition, when boric acid and pinacol are reacted, magnesium sulfate, sodium sulfate, etc. may be added as a dehydrating agent.

[0138] Examples of the olefin in step B1 include vinylcyclohexane, allylcyclohexane, vinylcyclopentane, and allylcyclopentane.

[0139] (C1 process) Step C1 is a step for producing an aromatic compound (7-5a) by Suzuki coupling reaction of the boric 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.

[0140] This 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), or THF at a temperature range of 20° C. to 100° C. Water may also be added as a solvent.

[0141] 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, and the like may be added as the ligand.

[0142] Examples of the base used in step C1 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0143] Furthermore, from the perspective of ease of synthesis, a more specific production method that is preferred is shown in the following reaction scheme. [Chemical Formula 54] (A1 process) [Chemical Formula 55] (B1 process)

[0144] [Chemical Formula 56] (C1 process) (Herein, n and l have the same meanings as n and l in formula (2).) In addition, as another example of the method for producing the aromatic compound of the present invention, for example, X of formula (7-5) 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 、R 41 is a group represented by formula (2), R 39 、R 40 、R 42 、R 43 、R 71 、R 72 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5 The aromatic compound (7-5b) containing a hydrogen atom can be produced by a method comprising the above-mentioned step A1 or B1 and the following step C2.

[0145] (Step C2): A step of reacting the boric acid ester obtained in Step A1 or Step B1 with 2,8-dibromoanthra[1,2-b:5,6-b′]dithiophene in the presence of a base and a palladium catalyst to produce an aromatic compound (7-5b).

[0146] The details of each step are shown below.

[0147] (C2 process) Step C2 is a step for producing an aromatic compound (7-5b) by Suzuki coupling reaction of the boric acid ester obtained in Step A1 or Step B1 with 2,8-bromoanthra[1,2-b:5,6-b′]dithiophene in the presence of a base and a palladium catalyst.

[0148] This 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.

[0149] Examples of the palladium catalyst in step C2 include palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, and the like may be added as the ligand.

[0150] Examples of the base used in step C2 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0151] Furthermore, from the perspective of ease of synthesis, a more specific reaction of step C2 is shown in the following reaction scheme.

[0152] [Chemical Formula 57] (C2 process) (Herein, n and l have the same meanings as n and l in formula (2).) In addition, as another example of the method for producing the aromatic compound of the present invention, for example, X of formula (7-5) 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 is a group represented by formula (2), R 39 、R 40 、R 42 、R 43 、R 71 、R 72 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5 The aromatic compound (7-5d) containing a hydrogen atom can be produced by a method involving the following step D1 and step C3 or a method involving the following step C4.

[0153] (Step D1): A step of converting an anthracenedithiophene derivative (7-5a) into a monolithium salt using butyl lithium, followed by using a brominating agent to synthesize a monobromoanthracenedithiophene derivative (7-5c).

[0154] (Step C3): A step of producing an aromatic compound (7-5d) by reacting a boric acid ester or a boric acid with the monobromoanthracenedithiophene derivative (7-5c) obtained in Step D1 in the presence of a base and a palladium catalyst.

[0155] (Step C4): A step of producing an aromatic compound (7-5d) by reacting the boric acid ester obtained in the above-mentioned Step A1 or Step B1 with a monobromoanthracenedithiophene derivative in the presence of a base and a palladium catalyst.

[0156] The details of each step are shown below.

[0157] (D1 process) The step D1 is a method of preparing a monobrominated form by converting an anthracenedithiophene derivative into a monolithium salt using 1 equivalent of butyllithium and reacting the salt with a brominating agent.

[0158] The monolithium salt can be prepared, for example, 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.

[0159] As the brominating agent, tetrabromomethane, 1,2-dibromotetrachloroethane, or the like can be used.

[0160] (C3 process) The step C3 is a step for producing an aromatic compound (7-5d) by subjecting a boric acid ester or a boric acid to a Suzuki coupling reaction with the monobromoanthracenedithiophene derivative (7-5c) obtained in the step D1 in the presence of a base and a palladium catalyst.

[0161] This 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.

[0162] Examples of the palladium catalyst in step C3 include palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The palladium catalyst may have a ligand, and Ruphos, Xantphos, Xphos, and the like may be added as the ligand.

[0163] Examples of the base used in step C3 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0164] (C4 process) The step C4 is a step for producing an aromatic compound (7-5d) by Suzuki coupling reaction of the boric acid ester obtained in the above-mentioned step A1 or step B1 with a monobromoanthracenedithiophene derivative in the presence of a base and a palladium catalyst.

[0165] This 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.

[0166] Examples of the palladium catalyst used in the C4 step include palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The palladium catalyst may also have a ligand, and Ruphos, Xantphos, Xphos, and the like may be added as the ligand.

[0167] Examples of the base used in step C4 include potassium tert-butoxide, sodium tert-butoxide, sodium hydroxide, and potassium hydroxide.

[0168] Furthermore, from the perspective of ease of synthesis, more specific production methods of step D1, step C3, and step C4 are shown in the following reaction scheme. [Chemical Formula 58] (D1 process) [Chemical Formula 59] (C3 process)

[0169] [Chemical Formula 60] (C4 process) (wherein, n and l have the same meanings as those in formula (2), R 45 Represents R represented by formula (7-5) 45 Same meaning.) In another example of the method for producing an aromatic compound of the present invention, for example, X 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 is a group represented by formula (2), R 39 、R 40 、R 41 、R 42 、R 43 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5The aromatic compound (7-1a) containing a hydrogen atom can be produced through the following steps E1 and F1.

[0170] (Step E1): A step of reacting an alkyl bromide derivative with magnesium to produce alkylmagnesium bromide.

[0171] (Step F1): A step of producing an aromatic compound (7-1a) by reacting an alkylzinc chloride derived from the alkylmagnesium bromide obtained in Step E1 with 2-bromobiphenyleno[1,2-b:5,6-b′]dithiophene in the presence of a palladium catalyst.

[0172] The details of each step are shown below.

[0173] (E1 process) This step E1 is a step of reacting an alkyl bromide derivative with magnesium to produce alkylmagnesium bromide.

[0174] The conditions for preparing the magnesium salt, ie, alkylmagnesium bromide, are, for example, using 1 to 2 equivalents of magnesium in a solvent such as THF or diethyl ether at a temperature range of 25°C to 60°C.

[0175] Examples of the alkyl bromide derivative used in step E1 include (2-bromoethyl)cyclohexane, (3-bromopropyl)cyclohexane, (2-bromoethyl)cyclopentane, and (3-bromopropyl)cyclopentane.

[0176] (F1 process) Step F1 is a step of producing an aromatic compound (7-1a) by reacting an alkylzinc chloride derived from the alkylmagnesium bromide obtained in Step E1 with 2-bromobiphenyleno[1,2-b:5,6-b′]dithiophene in the presence of a palladium catalyst.

[0177] As conditions for preparing alkylzinc chloride from alkylmagnesium bromide, zinc chloride can be used in a solvent such as THF or diethyl ether at a temperature ranging from 0°C to 25°C.

[0178] Examples of the palladium catalyst used in step F1 include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The reaction temperature is preferably in the range of 20°C to 60°C.

[0179] Furthermore, from the perspective of ease of synthesis, more specific preferred production methods of Step E1 and Step F1 are shown in the following reaction scheme. [Chemical Formula 61] (E1 process)

[0180] [Chemical Formula 62] (F1 process) (Herein, n and l have the same meanings as n and l in formula (2).) In another example of the method for producing an aromatic compound of the present invention, for example, X 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 and R 41 is a group represented by formula (2), R 39 、R 40 、R 42 、R 43 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5 The aromatic compound (7-1b) containing a hydrogen atom can be produced through the above-mentioned steps E1 and F2 described below.

[0181] (Step F2): a step of reacting an alkylzinc chloride derived from the alkylmagnesium bromide obtained in step E1 with 2,7-dibromobiphenylene[1,2-b:5,6-b']dithiophene in the presence of a palladium catalyst to produce an aromatic compound (7-1b).

[0182] The details of each step are shown below.

[0183] (F2 process) This step F2 is a step of producing an aromatic compound (7-1b) by reacting an alkylzinc chloride derived from the alkylmagnesium bromide obtained in step E1 with 2,7-dibromobiphenyleno[1,2-b:5,6-b′]dithiophene in the presence of a palladium catalyst.

[0184] As conditions for preparing alkylzinc chloride from alkylmagnesium bromide, zinc chloride can be used in a solvent such as THF or diethyl ether at a temperature ranging from 0°C to 25°C.

[0185] Examples of the palladium catalyst used in step F2 include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The reaction temperature is preferably in the range of 20°C to 60°C.

[0186] Furthermore, from the perspective of ease of synthesis, a more specific production method of step F2 is shown in the following reaction scheme.

[0187] [Chemical Formula 63] (F2 process) (Herein, n and l have the same meanings as n and l in formula (2).) In another example of the method for producing an aromatic compound of the present invention, for example, X 8 、X 9 is a sulfur atom, Y 5 、Y 6 CH, R 38 is a group represented by formula (2), R 39 、R 40 、R 42 、R 43 is a hydrogen atom, m and k in formula (2) are 0, and Z 1 ~Z 5 The aromatic compound (7-1d) containing a hydrogen atom can be produced through the above-mentioned steps E1 and the following steps D2 and F3.

[0188] (Step D2): A step of converting the dithienobiphenylene derivative (7-1a) into a monolithium salt using butyl lithium, followed by synthesizing a monobromodithienobiphenylene derivative (7-1c) using a brominating agent.

[0189] (Step F3): A method for producing an aromatic compound (7-1d) by reacting zinc chloride derived from magnesium bromide with the monobromodithienyl biphenyl derivative (7-1c) obtained in step D2 in the presence of a palladium catalyst.

[0190] The details of each step are shown below.

[0191] (D2 process) The step D2 is a step of preparing a dibromo compound by converting the dithienobiphenylene derivative (7-1a) into a monolithium salt using 1 equivalent or more of butyl lithium and reacting the salt with a brominating agent.

[0192] The monolithium salt can be prepared, for example, using 1.0 to 5.0 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.

[0193] As the brominating agent, tetrabromomethane, 1,2-dibromotetrachloroethane, or the like can be used.

[0194] (F3 process) This step F3 is a method for producing an aromatic compound (7-1d) by reacting zinc chloride derived from magnesium bromide with the monobromodithienyl biphenyl derivative (7-1c) obtained in step D2 in the presence of a palladium catalyst.

[0195] As a method for preparing zinc chloride, zinc chloride can be used in a solvent such as THF or diethyl ether at a temperature ranging from 0°C to 25°C.

[0196] Examples of the palladium catalyst used in step F3 include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)dichloropalladium. The reaction temperature is preferably in the range of 20°C to 60°C.

[0197] Furthermore, from the perspective of ease of synthesis, more specific production methods of step D2 and step F3 are shown in the following reaction scheme. [Chemical Formula 64] (D2 process)

[0198] [Chemical Formula 65] (F3 process) (wherein, n and l have the same meanings as those in formula (2), R 41 Represents R represented by formula (7-1) 41 Same meaning.) [2. Solution for forming an organic semiconductor layer] A solution for forming an organic semiconductor layer containing the compound of the present invention can be prepared by dissolving the compound in a solvent. As the solvent, any solvent can be used as long as it can dissolve the aromatic compound represented by formula (1-I) or formula (1-II). Among them, from the perspective of obtaining a suitable solvent drying speed when forming the organic semiconductor layer, an organic solvent having a boiling point of 100°C or higher at normal pressure is preferred.

[0199] The solvent for the organic semiconductor layer forming solution that can be used in the present invention is not particularly limited, and examples thereof include aromatic hydrocarbons such as toluene, mesitylene, o-xylene, cumene, pentylbenzene, cyclohexylbenzene, 1,2,4-trimethylbenzene, tetralin, and dihydroindene; anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, 2,6-dimethylanisole, ethylphenyl ether, butylphenyl ether, 1,2-methylenedimethylbenzene; Aromatic ethers such as oxybenzene 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, 1,4-difluorobenzene; thiophene, 3-chlorothiophene, 2-chlorothiophene, 3-methylthiophene, 2-methylthiophene, benzothiophene, 2-methylbenzothiophene, 2,3-dihydrobenzothiophene, furan, 3-methylfuran, 2-methylfuran, 2,5-dimethylfuran, Benzofuran, 2-methylbenzofuran, 2,3-dihydrobenzofuran, thiazole, oxazole, benzothiazole, benzoxazole, pyridine and other heteroaromatics; hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, decahydronaphthalene and other saturated hydrocarbons; dipropylene glycol dimethyl ether, dipropylene glycol diacetate, dipropylene glycol methyl-n-propyl ether, dipropylene glycol methyl ether acetate, 1,4-butanediol diacetate, 1,3-butanediol diacetate, 1,3-butanediol 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, diethylene glycol monobutyl ether acetate and other glycols; dimethyl phthalate, diethyl phthalate, dimethyl terephthalate, phenyl acetate, cyclohexanol acetate, 3-methoxybutyl acetate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl propionate, γ-butyrolactone and other esters; THF, 2-methoxymethyltetrahydrofuran and other cyclic ethers, etc. Among them, from the viewpoint of having a moderate drying speed, toluene, o-xylene, mesitylene, 1,2,4-trimethylbenzene, tetralin, indane, octane, nonane, decane, anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, 2,6-dimethylanisole, ethylphenyl ether, butylphenyl ether, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, 3-methylthiophene, and benzothiazole are preferred, and toluene, o-xylene, mesitylene, tetralin, indane, octane, nonane, decane, anisole, 2-methylanisole, 3-methylanisole, 2,3-dimethylanisole, 3,4-dimethylanisole, and 2,6-dimethylanisole are more preferred.

[0200] The solvent used in the solution for forming the organic semiconductor layer may be a single solvent or a mixture of two or more solvents having different properties such as boiling points, polarities, and solubility parameters.

[0201] The temperature for mixing and dissolving the aromatic compound represented by formula (1-I) or (1-II) in a solvent is preferably 0 to 80°C, more preferably 10 to 60°C, for the purpose of promoting dissolution.

[0202] In order to obtain a uniform solution, the time for dissolving and mixing the aromatic compound represented by Formula (1-I) or Formula (1-II) in the solvent is preferably set to 1 minute to 1 hour.

[0203] When the concentration of the aromatic compound represented by Formula (1-I) or Formula (1-II) in the organic semiconductor layer-forming solution is in the range of 0.1 to 10.0 wt%, handling becomes easier and the efficiency of forming the organic semiconductor layer is improved. Furthermore, when the viscosity of the organic semiconductor layer-forming solution is in the range of 0.3 to 10 mPa·s, more suitable coating properties are exhibited.

[0204] In addition, since the aromatic compound itself has moderate cohesiveness, the solution can be prepared at a relatively low temperature, and since the solution has oxidation resistance, it can be suitable for application in the manufacture of an organic film by a coating method. That is, since there is no need to remove air from the environment, the coating process can be simplified. Furthermore, in the solution, a polymer can also be present as a binder. Examples of the polymer 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), polystyrene Examples of the present invention include polyethers, polycarbonates, polycarbazoles, polytriarylamines, poly(9,9-dioctylfluorene-co-dimethyltriarylamine), poly(N-vinylcarbazole), polymethyl methacrylate, poly(styrene-co-methyl methacrylate), polyethyl methacrylate, poly-n-propyl methacrylate, polyisopropyl methacrylate, poly-n-butyl methacrylate, polyphenyl 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. To achieve an appropriate solution viscosity, the concentration of these polymer binders is preferably 0.001 to 10.0% by weight.

[0205] From the viewpoint of being more suitable for the process temperature during electronic device production, the glass transition temperature (Tg) of the polymer binder is preferably 105° C. or higher, more preferably 120° C. or higher, and particularly preferably 150° C. or higher.

[0206] In order to obtain an organic thin film transistor with higher carrier mobility, the molecular weight of the polymer 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.

[0207] This polymer has an effect as a general polymer binder and can improve the film-forming properties of the resulting organic semiconductor layer. Insulating polymers and semiconducting polymers can also be used.

[0208] As the polar cyclic polyolefins used as the polymer binder, more specifically, a polymer represented by the following formula (9) is more preferred.

[0209] [Chemical Formula 66] (Among them, R 62 ~R 64 Each of the following 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 alkoxycarbonyl 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 alkoxycarbonyl 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 aryloxycarbonyl 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 from 20 to 5,000, and q and r each independently represent an integer from 0 to 2. Bonds consisting of solid and dotted lines represent single or double bonds. R in formula (9) 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 alkoxycarbonyl 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. In order to achieve high heat resistance of the present polymer, a hydrogen atom or an alkyl group having 1 to 20 carbon atoms is preferred.

[0210] R 62 ~R 64Examples of the alkyl group having 1 to 20 carbon atoms include linear or branched alkyl groups such as methyl, ethyl, n-propyl, n-butyl, isobutyl, sec-butyl, and n-pentyl. Examples of the aryl group having 6 to 20 carbon atoms include phenyl, p-tolyl, p-(n-hexyl)phenyl, p-(n-octyl)phenyl, and p-(2-ethylhexyl)phenyl. Examples of the alkoxycarbonyl group having 2 to 20 carbon atoms include methoxycarbonyl, ethoxycarbonyl, and n-propoxycarbonyl. Examples of the aryloxycarbonyl group having 7 to 20 carbon atoms include phenoxycarbonyl and 4-methylphenoxycarbonyl. Examples of the alkoxy group having 1 to 20 carbon atoms include methoxy, ethoxy, and n-propoxy. Examples of the aryloxy group having 6 to 20 carbon atoms include phenoxy and 4-methylphenoxy. Examples of the alkylamino group having 1 to 20 carbon atoms include methylamino, ethylamino, and n-propylamino. Furthermore, in order to achieve high heat resistance of the present polymer, the substituent R 62 Preferably, methyl, ethyl or n-propyl, the substituent R 63 and R 64 Preferred is a hydrogen atom.

[0211] Z in formula (9) represents one selected from the group consisting of a halogen atom, an alkoxycarbonyl 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.

[0212] Examples of alkoxycarbonyl groups having 2 to 20 carbon atoms in the substituent Z include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, n-butoxycarbonyl, n-hexyloxycarbonyl, and cyclohexyloxycarbonyl. Examples of aryloxycarbonyl groups having 7 to 20 carbon atoms include phenoxycarbonyl, 4-methylphenoxycarbonyl, 2,4-dimethylphenoxycarbonyl, and 4-ethylphenoxycarbonyl. Examples of alkoxy groups having 1 to 20 carbon atoms include methoxy and ethoxy. Examples of aryloxy groups having 6 to 20 carbon atoms include phenoxy and 4-methylphenoxy. Examples of alkylamino groups having 1 to 20 carbon atoms include methylamino, ethylamino, and n-propylamino. For the high solubility and heat resistance of the present polymer, Z is preferably an alkoxycarbonyl group having 2 to 20 carbon atoms.

[0213] p represents an integer of 20 to 5,000, and is preferably 40 to 2,000 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.

[0214] The bonds consisting of solid and dotted lines represent single bonds or double bonds, and single bonds are preferred for thermal stability.

[0215] The polysulfones used as the polymer binder are not particularly limited as long as they have a polysulfone structure. More specific examples include the polysulfones represented by the following polysulfones 1 to 5.

[0216] [Chemical Formula 67] (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. Substituent R 65 ~R 68 Examples of the alkyl group having 1 to 20 carbon atoms include straight-chain or branched-chain 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.

[0217] s represents an integer of 10 to 20,000, and preferably an integer of 10 to 10,000.

[0218] The acrylonitrile-styrene copolymer used as the polymer binder is a copolymer of acrylonitrile and styrene in any ratio. From the perspective of improving reliability, such as exhibiting good electrical properties in the resulting organic thin-film transistor and minimizing changes in threshold voltage when bias stress is applied, the acrylonitrile-styrene copolymer preferably has a weight ratio of acrylonitrile to styrene of 10:90 to 50:50, and more preferably 20:80 to 40:60.

[0219] The methyl methacrylate-styrene copolymer used as the polymer binder is a copolymer of methyl methacrylate and styrene in any ratio. From the perspective of achieving excellent electrical properties in the resulting organic thin-film transistor and improved reliability, such as minimal change in threshold voltage when bias stress is applied, the methyl methacrylate-styrene copolymer preferably has a molar ratio of methyl methacrylate to styrene of 1:99 to 90:10, and more preferably 1:99 to 70:30.

[0220] As the polymer binder, a polymer whose surface energy has been adjusted using a surface treatment agent can be used. As the surface treatment agent, a silane coupling agent can be used. Specific examples thereof include 1,1,1,3,3,3-hexamethyldisilazane, phenyltrimethoxysilane, octyltrichlorosilane, β-phenylethyltrichlorosilane, and β-phenylethyltrimethoxysilane.

[0221] The polymer may be used alone or as a mixture of two or more polymers. Furthermore, polymers having different molecular weights may be mixed and used.

[0222] [3. Organic semiconductor layer] The coating method for forming an organic semiconductor layer using a solution for forming an organic semiconductor layer containing the compound of the present invention is not particularly limited as long as it is a method that can form an organic semiconductor layer. Examples thereof include simple coating methods such as spin coating, drop casting, dip coating, and cast coating; and printing methods such as dispenser coating, inkjet, slit coating, doctor blade coating, flexographic printing, screen printing, gravure printing, and offset printing. Among them, spin coating, drop casting, and inkjet are preferred from the viewpoint of being able to easily and efficiently form an organic semiconductor layer.

[0223] After applying the organic semiconductor layer-forming solution of the present invention to form a film of the organic semiconductor layer-forming solution, the film is dried to remove the solvent, thereby forming an organic semiconductor layer containing the compound of the present invention using the organic semiconductor layer-forming solution.

[0224] When the solvent is dried and removed from the film of the organic semiconductor layer-forming solution, the drying conditions are not particularly limited. For example, the solvent can be dried and removed under normal pressure or reduced pressure.

[0225] The temperature for drying and removing the solvent from the film of the organic semiconductor layer forming solution is not particularly limited. However, in order to efficiently dry and remove the solvent from the applied organic semiconductor layer and form the organic semiconductor layer, the temperature is preferably in the range of 10 to 150°C.

[0226] When the solvent is dried and removed from the film of the organic semiconductor layer forming solution, the crystal growth of the aromatic compound represented by Formula (1-I) or Formula (1-II) can be controlled by adjusting the vaporization rate of the removed solvent.

[0227] The film thickness of the organic semiconductor layer formed from the organic semiconductor layer-forming solution of the present invention is not limited, but is preferably in the range of 1 nm to 1 μm, more preferably in the range of 10 nm to 300 nm, from the viewpoint of achieving good carrier transport.

[0228] Alternatively, the obtained organic semiconductor layer may be subjected to an annealing treatment at 40 to 180° C. after the organic semiconductor layer is formed.

[0229] The organic semiconductor layer formed from the solution for forming an organic semiconductor layer of the present invention can be used as an organic semiconductor device including the organic semiconductor layer, and in particular, can be used as an organic thin-film transistor including the compound of the present invention including the organic semiconductor layer.

[0230] 〔4. Organic Thin Film Transistor〕 An organic thin-film transistor can be obtained by laminating an organic semiconductor layer, including a source electrode and a drain electrode, and a gate electrode on a substrate via an insulating layer. By using the organic semiconductor layer formed using the organic semiconductor layer-forming solution of the present invention, an organic thin-film transistor exhibiting excellent semiconductor and electrical properties can be produced.

[0231] Figure 1 The cross-sectional structure of a typical organic thin-film transistor is shown in FIG. Here, 1001 represents a bottom-gate-top contact type, 1002 represents a bottom-gate-bottom contact type, 1003 represents a top-gate-top contact type, and 1004 represents a top-gate-bottom contact type organic thin-film transistor. 1 represents an organic semiconductor layer, 2 represents a substrate, 3 represents a gate electrode, 4 represents a gate insulating layer, 5 represents a source electrode, and 6 represents a drain electrode. The organic semiconductor layer formed using the solution for forming an organic semiconductor layer of the present invention can be applied to any organic thin-film transistor.

[0232] The substrate is not particularly limited, and examples thereof include plastic substrates such as polyethylene terephthalate, polyethylene naphthalate, polymethyl methacrylate, polymethacrylate, polyethylene, polypropylene, polystyrene, cyclic polyolefins, fluorinated cyclic polyolefins, polyimides, polycarbonates, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), poly(diisopropyl maleate), polyethersulfone, polyphenylene sulfide, and cellulose triacetate; inorganic substrates such as glass, quartz, alumina, silicon, heavily doped silicon, silicon oxide, tantalum dioxide, tantalum pentoxide, and indium tin oxide; and metal substrates such as gold, copper, chromium, titanium, and aluminum. Furthermore, when heavily doped silicon is used as the substrate, the substrate can also serve as a gate electrode.

[0233] There is no particular limitation on the material of the gate, and examples thereof include inorganic materials such as aluminum, gold, silver, copper, heavily 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).

[0234] Furthermore, the aforementioned inorganic materials can be used without hindrance as metal nanoparticle inks. For optimal dispersibility, the solvent is preferably a polar solvent such as water, methanol, ethanol, 2-propanol, 1-butanol, or 2-butanol; an aliphatic hydrocarbon solvent with 6 to 14 carbon atoms such as hexane, heptane, octane, decane, dodecane, or tetradecane; or an aromatic hydrocarbon solvent with 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. After applying the nanoparticle ink, it is preferably annealed at a temperature between 80°C and 200°C to improve conductivity.

[0235] The material of 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, polymethacrylate, polyimide, polyamic acid polycarbonate, polyvinylphenol, polyvinyl alcohol, poly(diisopropyl fumarate), poly(diethyl fumarate), polyethylene terephthalate, polyethylene naphthalate, polyethyl 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, The Dow Chemical Company), Cytop (registered trademark), Teflon (registered trademark), Parylene (registered trademark) and other Parylene C-based polymer insulating materials. Among them, from the perspective of simplicity of production, the material for the gate insulating layer is preferably a polymer insulating material (polymer gate insulating layer) that can be applied by a coating method.

[0236] The solvent for dissolving 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 solvents such as THF, 1,2-dimethoxyethane, and dioxane; alcohol solvents such as ethanol, isopropanol, 1-butanol, 2-butanol, 2-ethylhexanol, and tetrahydrofurfuryl alcohol; ketone solvents such as acetone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, and acetophenone; ethyl acetate, γ-butyrolactone, cyclohexanol acetate, 3-methoxybutyl acetate, tetrahydrofurfuryl acetate, and tetrahydrofurfuryl propionate. Ester solvents such as furfuryl ester; amide solvents such as DMF and NMP; glycol solvents 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-butanediol 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; fluorinated solvents such as perfluorohexane, perfluorooctane, 2-(pentafluoroethyl)hexane, and 3-(pentafluoroethyl)heptane, etc.

[0237] The concentration of the polymer insulating material when dissolved in a solvent is, for example, 0.1 to 10.0 wt % at a temperature of 20 to 40° C. The thickness of the insulating layer obtained at this concentration is not limited, but is preferably 100 nm to 1 μm, more preferably 150 nm to 900 nm, from the viewpoint of insulation resistance.

[0238] The gate insulating layer may also be one whose surface has been modified with silanes such as octadecyltrichlorosilane, decyltrichlorosilane, decyltrimethoxysilane, octyltrichlorosilane, octyltrimethoxysilane, β-phenylethyltrichlorosilane, β-phenylethyltrimethoxysilane, phenyltrichlorosilane, and phenyltrimethoxysilane; phosphonic acids such as octadecylphosphonic acid, decylphosphonic acid, and octylphosphonic acid; or silylamines such as hexamethyldisilazane. Generally, surface treatment of the gate insulating layer increases the crystal size of the organic semiconductor material and improves molecular orientation, thereby achieving favorable results such as increased carrier mobility, current on / off ratio, and reduced threshold voltage.

[0239] As the material of the source and drain, there is no particular limitation, and the same material as the gate can be used, and it can be the same as the material of the gate, or it can be different, and different types of materials can also be stacked. In addition, in order to improve the injection efficiency of carriers, the surface of the source and drain can also be subjected to surface treatment. As the surface treatment agent for surface treatment, for example, benzenethiol, pentafluorobenzenethiol, 4-fluorobenzenethiol, 4-methoxybenzenethiol, etc. can be listed.

[0240] For high-speed operation, the carrier mobility of the organic thin film transistor of the present invention is preferably 0.10 cm 2 / V·sec or more.

[0241] The organic thin-film transistors of the present invention can be used in electronic materials such as organic semiconductor layers in transistors for electronic paper, organic EL displays, liquid crystal displays, IC tags (RFID tags), pressure sensors, and biosensors; organic EL display materials; organic semiconductor laser materials; organic thin-film solar cell materials; photonic crystal materials; and semiconductor materials for imaging devices. Furthermore, since the aromatic compounds represented by Formula (1-I) or Formula (1-II) form crystalline thin films, they are preferably used as semiconductor layers in organic thin-film transistors.

[0242] 〔in conclusion〕 A first aspect of the present invention is an aromatic compound represented by any one of the above formulas (1-I) or (1-II).

[0243] The second aspect of the present invention is that, in the first aspect, R 1 ~R 6 In, only R 1 and R 2 Either or only R 1 and R 2 Both are groups represented by the above-mentioned formula (2).

[0244] The third aspect of the present invention is that in the first or second aspect, the aromatic compound represented by formula (1-I) or (1-II) is a compound represented by one selected from the group consisting of formulas (3-1) to (3-6) above.

[0245] The fourth aspect of the present invention is that, in the third aspect, the aromatic compound represented by formula (1-I) or (1-II) is a compound represented by formula (3-1) or (3-2).

[0246] The fifth aspect of the present invention is that, in the third aspect or the fourth aspect, the above-mentioned formula (4-2) is the above-mentioned formula (4-3).

[0247] The sixth aspect of the present invention is that, in the third aspect or the fourth aspect, the above-mentioned formula (4-2) is the above-mentioned formula (4-4).

[0248] The seventh aspect of the present invention is that, in the first aspect or the second aspect, the aromatic compound represented by formula (1-I) or (1-II) is the compound represented by formula (5) or (5-2) described above.

[0249] The eighth aspect of the present invention is that, in the seventh aspect, the above-mentioned formula (6-2) is the above-mentioned formula (6-3).

[0250] The ninth aspect of the present invention is that, in the seventh aspect, the above-mentioned formula (6-2) is the above-mentioned formula (6-4).

[0251] The tenth aspect of the present invention is that in the first aspect or the second aspect, the aromatic compound represented by formula (1-I) or (1-II) is a compound represented by one selected from the group consisting of formulas (7-1) to (7-6) above.

[0252] The eleventh aspect of the present invention is that, in the tenth aspect, R 38 and R 41 are each independently one selected from the group consisting of a group represented by the above formula (2), a hydrogen atom and a fluorine atom, R 39 、R 40 、R 42 ~R 45 、R 71 and R 72 A hydrogen atom.

[0253] The twelfth aspect of the present invention is that in the tenth aspect or the eleventh aspect, R 38 and R 41 is a group represented by the above formula (2), R 39 、R 40 、R 42 ~R 45 、R 71 and R 72 A hydrogen atom.

[0254] A thirteenth aspect of the present invention is a solution for forming an organic semiconductor layer, comprising the aromatic compound according to any one of the first to twelfth aspects.

[0255] A thirteenth aspect of the present invention is an organic semiconductor layer comprising the aromatic compound according to any one of the first to twelfth aspects.

[0256] A thirteenth aspect of the present invention is an organic thin film transistor comprising the aromatic compound according to any one of the first to twelfth aspects. [Example]

[0257] Hereinafter, the present invention will be described in further detail with reference to Examples, but the present invention is not limited to these Examples.

[0258] Used in product identification 1 H NMR spectroscopy and liquid chromatography-mass spectrometry (LCMS) analysis.

[0259] <1 H NMR spectroscopy analysis> Device: JEOL Ltd., (trade name) Delta V5 (400MHz) Measurement temperature: 23°C (no temperature specified) Liquid chromatography-mass spectrometry (LCMS) analysis Device: Bruker Daltonics, (trade name) microTOF focus MS ionization: atmospheric pressure chemical ionization (APCI) method LC conditions: the conditions described in the following liquid chromatography analysis items Thin layer chromatography, gas chromatography (GC), and liquid chromatography (LC) analyses were used to confirm the progress of the reaction, and liquid chromatography analysis was also used to determine the purity of the aromatic compound.

[0260] Thin-layer chromatography analysis Merck PLC silica gel 60F254 0.5 mm was used for thin layer chromatography, and hexane and / or toluene was used as a developing solvent.

[0261] Gas chromatography analysis Device: Shimadzu Corporation, (trade name) GC2014 Column: RESTEK Co., Ltd. (trade name) Rxi-1HT, 30 m Liquid chromatography analysis Apparatus: Agilent Technologies, Inc. Model: 1260 Infinity II Column: Tosoh (trade 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 Aromatic compounds were purified using a recirculating preparative HPLC apparatus.

[0262] <Circulation Preparative HPLC> Device: Made by Japan Analytical Industry Co., Ltd., Model: LC-9160II NEXT Solvent: tetrahydrofuran Flow rate: 10ml / min The melting point of the aromatic compound was measured using DSC (differential scanning calorimetry).

[0263] <DSC measurement> Device: Made by SII Nano Technology Inc., Model: DSC6220 Heating speed: 10℃ / min Scanning range: -10℃~300℃ The transport characteristics of aromatic compounds were evaluated using a semiconductor parameter analyzer.

[0264] <Transmission characteristics measurement> Device: Made by KEITHLEY, Model: 4200A-SCS Drain voltage: -20V Gate voltage: 10V~-20V.

[0265] Synthesis Example 1 Synthesis of (2-bromoethyl)cyclohexane Under a nitrogen atmosphere, 5.03 g (39.2 mmol) of 2-cyclohexylethanol (Tokyo Chemical Industry) and 43 ml of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 200 mL two-necked flask. To this solution, 1.70 ml (17.9 mmol) of phosphorus tribromide (Fujifilm Wako Pure Chemical Industries, Ltd.) was added at room temperature, stirred for 20 minutes, and then stirred at 100°C for 3 hours. The reaction solution was poured into ice, neutralized with saturated aqueous sodium bicarbonate solution, and then toluene was added for phase separation. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 5.31 g (68% yield) of (2-bromoethyl)cyclohexane as a colorless liquid.

[0266] 1 H NMR (CDCl3): δ=3.44 (t, J=7.3Hz, 2H), 1.79-1.64 (m, 7H), 1.52-1.41 (m, 1H), 1.30-1.09 (m, 3H), 0.96-0.86 (m, 2H).

[0267] ((2-Bromoethyl)cyclohexane)

[0268] [Chemical Formula 68] Synthesis Example 2 Synthesis of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Under a nitrogen atmosphere, 809 mg (1.40 mmol) of Xantphos (Tokyo Chemical Industry), 8.49 g (33.4 mmol) of bis(pinacolato)diboron (Tokyo Chemical Industry), 140 mg (1.42 mmol) of copper(I) chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), 4.06 g (36.2 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, dehydrated grade), and 20 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 200 ml Schlenk reaction vessel and stirred at room temperature for 30 minutes. Under ice cooling, 19 ml of a THF solution of 5.31 g (27.8 mmol) of (2-bromoethyl)cyclohexane synthesized in Synthesis Example 1 (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) was added, and the mixture was stirred at 0°C for 25 minutes and then at room temperature for 4 hours. The reaction mixture was ice-cooled, water was added, and then toluene was added for phase separation. 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 5.46 g (yield 81%) of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless liquid.

[0269] 1 H NMR (CDCl3): δ=1.72-1.59(m,5H), 1.32-1.26(m,2H), 1.25(s,12H), 1.22-1.08(m,4H), 0.88-0.74(m,4H).

[0270] (2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

[0271] [Chemical Formula 69] Synthesis Example 3 Synthesis of 2-hexylanthra[1,2-b:5,6-b']dithiophene Under a nitrogen atmosphere, 716 mg (purity 65%, 1.26 mmol) of 2-bromoanthraquinone [1,2-b: 5,6-b'] dithiophene (compound 22 in the publication) synthesized by the method described in WO2021 / 177417, 67.0 mg (0.298 mmol) of palladium (II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 278 mg (0.596 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 487 mg (3.64 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 509 mg (3.91 mmol) of hexylboronic acid (Tokyo Chemical Industry Co., Ltd.) were added to a 200 mL Schlenk tube. 45 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 3.0 mL of water were added thereto and stirred at 80 ° C for 2.5 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using diatomaceous earth (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane) to obtain 100 mg (yield 49%) of 2-hexylanthra[1,2-b:5,6-b′]dithiophene as a yellow solid.

[0272] 1 H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=6.6Hz,1H),7.87(d,J= 6.4Hz,1H),7.82(d,J=8.7Hz,1H),7.73(d,J=8.7Hz,1H),7.54(d,J=5.2Hz,1 H),7.49(d,J=5.1Hz,1H),7.16(s,1H),3.02(t,J=8.0Hz,2H),1.91(dt,J=7. 6Hz, J=7.6Hz, 2H), 1.51-1.44 (m, 2H), 1.39-1.32 (m, 4H), 0.94-0.90 (m, 3H).

[0273] (2-Hexylanthra[1,2-b:5,6-b']dithiophene)

[0274] [Chemical Formula 70] Synthesis Example 4 2-Bromo-8-hexylanthra[1,2-b:5,6-b']dithiophene Under a nitrogen atmosphere, 246 mg (0.655 mmol) of 2-hexylanthraquinone [1,2-b:5,6-b']dithiophene synthesized in Synthesis Example 3 and 10 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk reactor. The mixture was cooled to -78°C, and 1.50 mL (2.40 mmol) of 1.6 M n-butyl lithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added. The mixture was stirred at -78°C for 3 hours. 864 mg (2.65 mmol) of 1,2-dibromotetrachloroethane was added at -78°C, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 234 mg (78% yield) of 2-bromo-8-hexylanthraquinone [1,2-b:5,6-b']dithiophene as a yellow solid.

[0275] 1 H NMR (CDCl3): δ=8.59(s,1H),8.52(s,1H),7.87(d,J=6.0Hz,1H),7.84(d,J=6.0Hz,1H),7.73(d,J=8.9Hz,1H),7.68(d,J=8.8Hz,1H),7.4 6(s,1H),7.16(s,1H),3.01(t,J=7.3Hz,2H),1.83(dt,J=7.6Hz,J=7.6Hz,2H),1.49-1.43(m,2H),1.39-1.32(m,4H),0.94-0.90(m,3H).

[0276] (2-Bromo-8-hexylanthra[1,2-b:5,6-b']dithiophene)

[0277] [Chemical Formula 71] Example 1 Synthesis of 2-(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 1) Under a nitrogen atmosphere, 605 mg (60% purity, 0.983 mmol) of 2-bromoanthra[1,2-b:5,6-b']dithiophene (Compound 22 in the publication), synthesized by the method described in WO2021 / 177417, 55.8 mg (0.249 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 231 mg (0.494 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 409 mg (3.64 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were added to a 200 mL Schlenk tube. To this was added 38 mL of a toluene solution of 799 mg (3.36 mmol) of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) synthesized in Synthesis Example 2 and 3.0 mL of water, and the mixture was stirred at 80°C for 23 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 purified by recirculating HPLC and recrystallized from hexane / toluene = 1 / 1 to obtain 186 mg (yield 47%) of 2-(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 1) as a yellow solid.

[0278] 1 H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=6.4Hz,1H),7.87(d,J=6.4Hz,1H),7.82(d,J=8.8Hz,1H),7.72(d,J=8.7Hz,1H),7.53(d,J=5 .5Hz,1H),7.48(d,J=5.0Hz,1H),7.16(s,1H),3.03(t,J=8.2Hz,2H),1.8 7-1.64(m,7H),1.47-1.36(m,1H),1.32-1.13(m,3H),1.05-0.95(m,2H).

[0279] Melting point: 161°C (Compound 1)

[0280] [Chemical Formula 72] Example 2 Synthesis of 2,8-bis(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 2) Under a nitrogen atmosphere, 75.0 mg (0.167 mmol) of 2,8-dibromoanthra[1,2-b:5,6-b']dithiophene (Compound 20 in the publication), synthesized by the method described in WO2021 / 177417, 9.5 mg (0.042 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 42.0 mg (0.0900 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 149 mg (1.33 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were added to a 100 mL Schlenk tube. To this was added 6.5 mL of a toluene solution of 274 mg (1.15 mmol) of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) synthesized in Synthesis Example 2 and 0.5 mL of water, and the mixture was stirred at 80°C for 25 hours. The reaction mixture was cooled to room temperature, and insoluble matter was removed using celite (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). The resulting solid was recrystallized from hexane to obtain 25.8 mg (30% yield) of 2,8-bis(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 2) as a yellow solid.

[0281] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.8Hz,2H),7.69(d,J=8.9Hz,2H),7.15(s,2H),3.03( t,J=7.2Hz,4H),1.84-1.65(m,14H),1.48-1.37(m,2H),1.32-1.16(m,6H),1.05-0.95(m,4H).

[0282] Melting point: 217°C (Compound 2)

[0283] [Chemical Formula 73] Example 3 Synthesis of 2-bromo-8-(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 3) Under a nitrogen atmosphere, 150 mg (0.375 mmol) of Compound 1 synthesized in Example 1 and 10 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 100 mL Schlenk reactor. The mixture was cooled to -78°C, and 0.50 mL (0.80 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added. The mixture was stirred at -78°C for 10 minutes and then at room temperature for 1 hour. After cooling to -78°C, 345 mg (1.06 mmol) of 1,2-dibromotetrachloroethane was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 155 mg (82% yield) of 2-bromo-8-(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 3) as a yellow solid.

[0284] 1 H NMR (CDCl3): δ=8.59(s,1H),8.53(s,1H),7.87(d,J=6.0Hz,1H),7.85(d,J=6.0Hz,1H),7.73(d,J=8.8Hz,1H),7.69(d,J=8.9Hz,1 H),7.46(s,1H),7.16(s,1H),3.04(t,J=7.5Hz,2H),1.86-1.66(m,7H),1.46-1.38(m,1H),1.32-1.12(m,3H),1.05-0.98(m,2H).

[0285] (Compound 3)

[0286] [Chemical Formula 74] Example 4 Synthesis of 2-(2-cyclohexylethyl)-8-propylanthraquinone[1,2-b:5,6-b']dithiophene (Compound 4) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 49.5 mg (0.103 mmol) of compound 3 synthesized in Example 3, 7.4 mg (0.033 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 30.6 mg (0.0656 mmol) of Ruphos (Tokyo Chemical Industry, Ltd.), 53.0 mg (0.472 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, Ltd.), and 36.7 mg (0.417 mmol) of propylboronic acid (Tokyo Chemical Industry, Ltd.). To this mixture was added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 2.5 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 13.2 mg (yield 28%) of 2-(2-cyclohexylethyl)-8-propylanthraquino[1,2-b:5,6-b′]dithiophene (Compound 4) as a yellow solid.

[0287] 1 H NMR (CDCl3): δ=8.59(s,2H),7.85(d,J=8.7Hz,2H),7.70(d,J=8.7Hz,1H),7.70(d,J=8.7Hz,1H),7.16(s,1H),7.15(s,1H ),3.05-2.98(m,4H),1.89-1.65(m,9H),1.46-1.38(m,1H),1.32-1.17(m,3H),1.08(t,J=7.3Hz,3H),1.04-0.96(m,2H).

[0288] Melting point: 144°C (Compound 4)

[0289] [Chemical Formula 75] Example 5 Synthesis of 2-(2-cyclohexylethyl)-8-isobutylanthra[1,2-b:5,6-b']dithiophene (Compound 5) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 49.3 mg (0.103 mmol) of compound 3 synthesized in Example 3, 6.9 mg (0.031 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 29.2 mg (0.0626 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 52.6 mg (0.469 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 43.0 mg (0.422 mmol) of isobutylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture, 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water were added, and the mixture was stirred at 80°C for 2 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 15.8 mg (yield 33%) of 2-(2-cyclohexylethyl)-8-isobutylanthraquinone[1,2-b:5,6-b′]dithiophene (Compound 5) as a yellow solid.

[0290] 1 H NMR (CDCl3): δ=8.59(s,2H),7.85(d,J=8.8Hz,2H),7.71(d,J=8.8Hz,1H),7.70(d,J=8.8Hz,1H),7.15(s,1H),7.14(s,1H),3.03(t,J=7.8Hz,2H) ,2.88(d,J=7.2Hz,2H),2.13-2.03(m,1H),1.85-1.66(m,7H),1.47-1.37 (m,1H),1.32-1.16(m,3H),1.06(s,3H),1.04(s,3H),1.01-0.95(m,2H).

[0291] Melting point: 166°C (Compound 5)

[0292] [Chemical Formula 76] Example 6 Synthesis of 2-butyl-8-(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 6) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 29.7 mg (0.0619 mmol) of compound 3 synthesized in Example 3, 5.0 mg (0.022 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 20.5 mg (0.0439 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 28.7 mg (0.256 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 22.2 mg (0.218 mmol) of butylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture was added 3.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.3 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane). The obtained solid was purified by recrystallization from heptane to obtain 10.2 mg (yield 36%) of 2-butyl-8-(2-cyclohexylethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 6) as a yellow solid.

[0293] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.7Hz,2H),7.16-7.14(m,2H),3.05-3.00 (m,4H),1.86-1.64(m,9H),1.52-1.47(m,2H),1.45-1.38(m,1H),1.31-1.16(m,3H),1.05-0.95(m,5H).

[0294] Melting point: 140°C (Compound 6)

[0295] [Chemical Formula 77] Example 7 Synthesis of 2-(2-cyclohexylethyl)-8-pentylanthraquinone[1,2-b:5,6-b']dithiophene (Compound 7) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 25.2 mg (0.0526 mmol) of compound 3 synthesized in Example 3, 5.8 mg (0.026 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 24.0 mg (0.0514 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 21.4 mg (0.185 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 21.4 mg (0.185 mmol) of amylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture, 2.5 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.25 mL of water were added, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane). The obtained solid was purified by recrystallization from heptane to obtain 9.9 mg (yield 40%) of 2-(2-cyclohexylethyl)-8-pentylanthraquinone[1,2-b:5,6-b′]dithiophene (Compound 7) as a yellow solid.

[0296] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.8Hz,2H),7.16-7.15(m,2H),3.04(d,J=7.0Hz,2H),3. 00(d,J=7.0Hz,2H),1.87-1.66(m,9H),1.49-1.39(m,5H),1.28-1.12(m,3H),1.04-0.98(m,2H),0.95(d,J=7.1Hz,2H).

[0297] Melting point: 148°C (Compound 7)

[0298] [Chemical Formula 78] Example 8 Synthesis of 2-(2-cyclohexylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 8) Under a nitrogen atmosphere, 60.5 mg (0.133 mmol) of 2-bromo-8-hexylanthra[1,2-b:5,6-b']dithiophene synthesized in Synthesis Example 4, 9.2 mg (0.041 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 38.1 mg (0.0816 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 62.9 mg (0.560 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were added to a 50 mL Schlenk tube. To this was added 6.0 mL of a toluene solution of 128 mg (0.539 mmol) of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 2 (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 24 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane). The resulting solid was recrystallized from hexane to obtain 18.2 mg (yield 28%) of 2-(2-cyclohexylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 8) as a yellow solid.

[0299] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.8Hz,2H),7.15-7.14(m,2H),3.04 (d, J=7.2Hz, 2H), 3.00 (d, J=7.0Hz, 2H), 1.85-1.69 (m, 9H), 1.47-1.17 (m, 12H), 1.04-0.89 (m, 5H).

[0300] Melting point: 133°C (Compound 8)

[0301] [Chemical Formula 79] Synthesis Example 5 Synthesis of (2-bromoethyl)cyclopentane Under a nitrogen atmosphere, 4.55 g (39.8 mmol) of 2-cyclopentylethanol (Tokyo Chemical Industry) and 40 ml of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 200 ml two-necked flask. To this solution, 1.70 ml (17.9 mmol) of phosphorus tribromide (Fujifilm Wako Pure Chemical Industries, Ltd.) was added at room temperature, stirred for 20 minutes, and then stirred at 100°C for 3 hours. The reaction solution was poured into ice, neutralized with saturated aqueous sodium bicarbonate solution, and then toluene was added for phase separation. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3.63 g (2-bromoethyl)cyclopentane) as a colorless liquid (yield 51%).

[0302] 1 H NMR (CDCl3): δ=3.42 (t, J=7.8Hz, 2H), 1.99-1.77 (m, 5H), 1.66-1.50 (m, 4H), 1.15-1.06 (m, 2H).

[0303] ((2-Bromoethyl)cyclopentane)

[0304] [Chemical formula 80] Synthesis Example 6 Synthesis of 2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Under a nitrogen atmosphere, 506 mg (0.874 mmol) of Xantphos (Tokyo Chemical Industry), 4.49 g (17.7 mmol) of bis(pinacolato)diboron (Tokyo Chemical Industry), 85.1 mg (0.860 mmol) of copper(I) chloride (Fujifilm Wako Pure Chemical Industries, Ltd.), 2.16 g (19.2 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, dehydrated grade), and 12 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 100 ml Schlenk reactor and stirred at room temperature for 1.5 hours. Under ice cooling, 8 ml of a THF solution of 2.63 g (14.8 mmol) of (2-bromoethyl)cyclopentane synthesized in Synthesis Example 5 (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) was added, and the mixture was stirred at 0°C for 10 minutes and at room temperature for 20 hours. The reaction mixture was ice-cooled, water was added, and then toluene was added for phase separation. 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 2.77 g (yield 80%) of 2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless liquid.

[0305] 1H NMR (CDCl3): δ = 1.77-1.66 (m, 3H), 1.59-1.38 (m, 6H), 1.24 (s, 12H), 1.12-1.04 (m, 2H), 0.7 (t, J = 8.4Hz, 2H).

[0306] (2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

[0307] [Chemical Formula 81] Example 9 Synthesis of 2-(2-cyclopentylethyl)anthraquinone[1,2-b:5,6-b']dithiophene (Compound 9) Under a nitrogen atmosphere, 603 mg (purity 60%, 0.980 mmol) of 2-bromoanthraquinone[1,2-b:5,6-b']dithiophene (Compound 22 in the publication) synthesized by the method described in WO2021 / 177417, 59.8 mg (0.266 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 249 mg (0.533 mmol) of Ruphos (Tokyo Chemical Industry) and 465 mg (4.14 mmol) of potassium tert-butoxide (Tokyo Chemical Industry) were added to a 200 mL Schlenk tube. To this was added 20 mL of a toluene solution (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) of 747 mg (3.36 mmol) of 2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, synthesized in Synthesis Example 6, and 3.0 mL of water, and the mixture was stirred at 80°C for 24 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 purified by recirculating HPLC and recrystallized from heptane / toluene = 20 / 1 to obtain 128 mg (34% yield) of 2-(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 9) as a yellow solid.

[0308] 1H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=6.2Hz,1H),7.87(d,J=6.3Hz,1H),7.82(d,J=8.8Hz,1H),7.72(d,J=8.8Hz,1H),7. 54(d,J=5.6Hz,1H),7.49(d,J=5.1Hz,1H),7.17(s,1H),3.05(t,J=7.7Hz,2H),1.96-1.83(m,5H),1.69-1.56(m,4H),1.25-1.16(m,2H).

[0309] (Compound 9)

[0310] [Chemical Formula 82] Example 10 Synthesis of 2,8-bis(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 10) Under a nitrogen atmosphere, 213 mg (0.476 mmol) of 2,8-dibromoanthra[1,2-b:5,6-b']dithiophene (Compound 20 in the publication), synthesized by the method described in WO2021 / 177417, 29.4 mg (0.131 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 126 mg (0.270 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 275 mg (2.45 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were added to a 200 mL Schlenk tube. A toluene solution of 458 mg (2.04 mmol) of 2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 2.0 mL of water were added to the mixture, and the mixture was stirred at 80°C for 25 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane). The resulting solid was recrystallized from heptane to obtain 57.5 mg (yield 25%) of 2,8-bis(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 10) as a yellow solid.

[0311] 1H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.9Hz,2H),7.16(s,2 H), 3.04 (t, J = 8.4Hz, 4H), 1.97-1.83 (m, 10H), 1.70-1.56 (m, 8H), 1.25-1.16 (m, 4H).

[0312] Melting point: 188°C (Compound 10)

[0313] [Chemical Formula 83] Example 11 Synthesis of 2-bromo-8-(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 11) Under a nitrogen atmosphere, 150 mg (0.389 mmol) of Compound 10 synthesized in Example 10 and 10 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 100 ml Schlenk reactor. The mixture was cooled to -78°C, and 0.80 mL (1.28 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added. The mixture was stirred at -78°C for 15 minutes and then at room temperature for 1 hour. After cooling to -78°C, 466 mg (1.43 mmol) of 1,2-dibromotetrachloroethane was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 145 mg (77% yield) of 2-bromo-8-(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 11) as a yellow solid.

[0314] 1 H NMR (CDCl3): δ=8.59(s,1H),8.52(s,1H),7.87(d,J=5.9Hz,1H),7.84(d,J=5.7Hz,1H),7.73(d,J=8.8Hz,1H),7.68(d,J =8.8Hz,1H),7.46(s,1H),7.17(s,1H),3.03(t,J=7.6Hz,2H),1.98-1.83(m,5H),1.70-1.55(m,4H),1.25-1.16(m,2H).

[0315] (Compound 11)

[0316] [Chemical Formula 84] Example 12 Synthesis of 2-(2-cyclopentylethyl)-8-isobutylanthra[1,2-b:5,6-b']dithiophene (Compound 12) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 45.9 mg (0.0986 mmol) of Compound 11 synthesized in Example 11, 5.5 mg (0.024 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 23.3 mg (0.0499 mmol) of Ruphos (Tokyo Chemical Industry, Ltd.), 35.4 mg (0.315 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, Ltd.), and 25.8 mg (0.253 mmol) of isobutylboronic acid (Tokyo Chemical Industry, Ltd.). To this mixture was added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 24 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 12.6 mg (yield 29%) of 2-(2-cyclohexylethyl)-8-isobutylanthraquinone[1,2-b:5,6-b′]dithiophene (Compound 12) as a yellow solid.

[0317] 1 H NMR (CDCl3): δ = 8.56 (s, 2H), 7.85 (d, J = 8.8Hz, 2H), 7.71 (d, J = 9.0Hz, 1H), 7.70 (d, J = 8.8Hz, 1H), 7.16 (s, 1H), 7.14 (s, 1H), 3.04 (t, J = 8.5Hz,2H),2.88(d,J=7.2Hz,2H),2.11-2.03(m,1H),1.97-1.83(m,5H),1.71-1.54(m,4H),1.25-1.16(m,2H),1.05(d,J=6.6Hz,6H).

[0318] Melting point: 151°C (Compound 12)

[0319] [Chemical Formula 85] Example 13 Synthesis of 2-(2-cyclopentylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 13) Under a nitrogen atmosphere, 58.9 mg (0.130 mmol) of 2-bromo-8-hexylanthra[1,2-b:5,6-b']dithiophene synthesized in Synthesis Example 4, 9.5 mg (0.042 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 40.6 mg (0.0870 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 53.5 mg (0.477 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.) were added to a 50 mL Schlenk tube. To this was added 6.0 mL of a toluene solution of 87.1 mg (0.389 mmol) of 2-(2-cyclopentylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 6 (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 27 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane). The resulting solid was recrystallized from hexane to obtain 10.7 mg (yield 17%) of 2-(2-cyclopentylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 13) as a yellow solid.

[0320] 1 H NMR (CDCl3): δ = 8.58 (s, 2H), 7.84 (d, J = 8.8Hz, 2H), 7.70 (d, J = 8.8Hz, 2H), 7.16-7.15 (m, 2H), 3.03 (t, J = 7.8Hz, 2H), 3.01 (t, J = 7.8Hz,2H),1.97-1.79(m,7H),1.71-1.55(m,4H),1.49-1.43(m,2H),1.40-1.32(m,4H),1.25-1.16(m,2H),0.93-0.89(m,3H).

[0321] Melting point: 134°C (Compound 13)

[0322] [Chemical Formula 86] Example 14 Synthesis of 2-(2-cyclohexylethyl)-8-(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 14) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 46.7 mg (0.100 mmol) of Compound 11 synthesized in Example 11, 5.5 mg (0.025 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 22.5 mg (0.0482 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), and 49.4 mg (0.440 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.). To this, 5.0 mL of a toluene solution of 90.2 mg (0.379 mmol) of 2-(2-cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 2 (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water were added, and the mixture was stirred at 80°C for 27 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: hexane), and the resulting solid was recrystallized from heptane to obtain 13.8 mg (yield 27%) of 2-(2-cyclohexylethyl)-8-(2-cyclopentylethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 14) as a yellow solid.

[0323] 1H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.9Hz,2H),7.16-7.15(m,2H),3.03(t,J=7 .5Hz,4H),1.96-1.82(m,7H),1.77-1.57(m,8H),1.47-1.37(m,1H),1.32-1.16(m,6H),1.05-0.95(m,2H).

[0324] Melting point: 186°C (Compound 14)

[0325] [Chemical Formula 87] Synthesis Example 7 Synthesis of 2-(3-cyclohexylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Under a nitrogen atmosphere, under ice cooling, 50.0 mL (45.0 mmol) of 8.5% borane / THF solution (Tokyo Chemical Industry) and 3.45 mL (22.5 mmol) of allylcyclohexane (Tokyo Chemical Industry) were added to a 200 mL two-necked flask, and the mixture was stirred at 0°C for 1 hour and at room temperature for 1.5 hours. Under ice cooling, 6.1 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 an 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 (3-cyclohexylpropyl)boric acid.

[0326] Under a nitrogen atmosphere, the obtained boronic acid was added to a 300 mL two-necked flask. 3.32 g (28.1 mmol) of pinacol (Tokyo Chemical Industry) and 25.0 mL of diethyl ether (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added, and the mixture was stirred at room temperature. 3.51 g (29.1 mmol) of magnesium sulfate (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at room temperature for 4 hours. The solid was removed by vacuum filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene) to obtain 2.53 g (yield 29%) of 2-(2-cyclohexylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless liquid.

[0327] (2-(3-cyclohexylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

[0328] [Chemical Formula 88] Example 15 Synthesis of 2-(3-cyclohexylpropyl)anthraquinone[1,2-b:5,6-b']dithiophene (Compound 15) Under a nitrogen atmosphere, 706 mg of a mixture of 2-bromoanthraquinone[1,2-b:5,6-b']dithiophene (Compound 22 in the publication) and 2,8-dibromoanthraquinone[1,2-b:5,6-b']dithiophene (Compound 20 in the publication) synthesized by the method described in WO2021 / 177417, 85.0 mg (0.379 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 358 mg (0.767 mmol) of Ruphos (Tokyo Chemical Industry), and 705 mg (6.28 mmol) of potassium tert-butoxide (Tokyo Chemical Industry) were added to a 200 mL Schlenk tube. To this was added 60 mL of a toluene solution (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) of 1.48 g (5.88 mmol) of 2-(2-cyclohexylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, synthesized in Synthesis Example 7, and 6.0 mL of water, and the mixture was stirred at 80°C for 2 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 recirculating HPLC and purified by recrystallization from heptane / toluene = 10 / 1 to obtain 247 mg of 2-(3-cyclohexylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 15) as a yellow solid.

[0329] 1 H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=8.7Hz,1H),7.87(d,J=8.7Hz,1H),7.82(d,J=8.9Hz,1H),7.73(d,J=8.8Hz,1H),7.54(d,J=5 .1Hz,1H),7.49(d,J=5.1Hz,1H),7.16(s,1H),3.00(t,J=7.2Hz,2H),1.8 8-1.81(m,2H),1.78-1.65(m,5H),1.38-1.11(m,6H),0.96-0.88(m,2H).

[0330] (Compound 15)

[0331] [Chemical Formula 89] Example 16 Synthesis of 2,8-bis(3-cyclohexylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 16) The remaining components obtained by the recycle HPLC purification in Example 15 were purified by recrystallization from heptane / toluene = 10 / 1 to obtain 86.7 mg of 2,8-bis(3-cyclohexylpropyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 16) as a yellow solid.

[0332] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,2H),3.00(t ,J=7.3Hz,4H),1.88-1.80(m,4H),1.77-1.64(m,10H),1.38-1.10(m,12H),0.96-0.86(m,4H).

[0333] Melting point: 169°C (Compound 16)

[0334] [Chemical formula 90] Example 17 Synthesis of 2-bromo-8-(3-cyclohexylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 17) Under a nitrogen atmosphere, 203 mg (0.489 mmol) of compound 15 synthesized in Example 15 and 10 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 ml Schlenk reactor. The mixture was cooled to -78°C, 1.10 mL (1.76 mmol) of 1.6 M n-butyl lithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at -78°C for 2 hours. After cooling to -78°C, 638 mg (1.96 mmol) of 1,2-dibromotetrachloroethane was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 227 mg (93% yield) of 2-bromo-8-(3-cyclohexylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 17) as a yellow solid.

[0335] 1H NMR (CDCl3): δ=8.59(s,1H),8.52(s,1H),7.86(d,J=8.7Hz,1H),7.85(d,J=8.7Hz,1H),7.73(d,J=8.8Hz,1H),7.69(d,J=8.8Hz,1 H),7.46(s,1H),7.16(s,1H),3.00(t,J=7.4Hz,2H),1.88-1.80(m,2H),1.77-1.64(m,5H),1.38-1.10(m,6H),0.96-0.87(m,2H).

[0336] (Compound 17)

[0337] [Chemical Formula 91] Example 18 Synthesis of 2-(3-cyclohexylpropyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 18) Under a nitrogen atmosphere, 51.0 mg (0.103 mmol) of Compound 17 synthesized in Example 17, 5.00 mg (0.0223 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 21.8 mg (0.0467 mmol) of Ruphos (Tokyo Chemical Industry, Ltd.), 41.7 mg (0.372 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, Ltd.), and 44.5 mg (0.342 mmol) of hexylboronic acid (Tokyo Chemical Industry, Ltd.) were added to a 50 mL Schlenk tube. To this mixture were added 6.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.60 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 22.7 mg (yield 44%) of 2-(3-cyclohexylpropyl)-8-hexylanthra[1,2-b:5,6-b′]dithiophene (Compound 18) as a yellow solid.

[0338] 1H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.16(s,2H),3.02(t,J=7.9Hz,2H),2.98 (t,J=8.3Hz,2H),1.87-1.79(m,4H),1.77-1.63(m,5H),1.51-1.43(m,2H),1.38-1.13(m,10H),0.96-0.87(m,5H).

[0339] Melting point: 132°C (Compound 18)

[0340] [Chemical Formula 92] Synthesis Example 8 Synthesis of (2-cyclohexylethyl)magnesium bromide Under a nitrogen atmosphere, 174 mg (7.15 mmol) of magnesium (Fujifilm Wako Pure Chemical Industries, Ltd., in the form of crumbs) was added to a 30 mL two-necked flask and stirred under vacuum. A 15 mL solution of 1.15 g (6.01 mmol) of (2-bromoethyl)cyclohexane synthesized in Synthesis Example 1 in THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3.5 hours. The solids were removed by filtration to obtain a 0.4 M (2-cyclohexylethyl)magnesium bromide / THF solution.

[0341] [Chemical Formula 93] Example 19 Synthesis of 2-(2-cyclohexylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 19) Under a nitrogen atmosphere, 203 mg (1.49 mmol) of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) and 5 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk tube and stirred under ice-cooling. Under ice-cooling, 1.50 mL (0.600 mmol) of the 0.4 M (2-cyclohexylethyl)magnesium bromide / THF solution prepared in Synthesis Example 8 was added, and the mixture was stirred at 0°C for 30 minutes and at room temperature for 2 hours to prepare a zinc reagent solution.

[0342] 120 mg (purity 86%, 0.300 mmol) of 2-bromobiphenylene [1,2-b:5,6-b'] dithiophene (compound 21 in the publication) synthesized by the method described in WO2021 / 177417 and 12.5 mg (0.0171 mmol) of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (II) (Sigma-Aldrich) were added thereto. The mixture was stirred at room temperature for 19 hours. The reaction mixture was ice-cooled, 1 M hydrochloric acid was added, and toluene was added for phase separation. 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 chromatography (solvent: toluene). The obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 59.6 mg (yield 53%) of 2-(2-cyclohexylethyl)biphenyleno[1,2-b:5,6-b′]dithiophene (Compound 19) as an orange-red solid.

[0343] 1H NMR (CDCl3): δ=7.18(d,J=7.6Hz,1H),7.18(d,J=6.0Hz,1H),7.03(d,J=5.6Hz,1H),7.01(d,J=7.6Hz,1H),6.70(d,J=7.6H z,1H),6.70(s,1H),6.66(d,J=7.6Hz,1H),2.80(t,J=7.6Hz,2H),1.78-1.57(m,7H),1.38-1.10(m,4H),0.99-0.86(m,2H).

[0344] Melting point: 134°C

[0345] [Chemical Formula 94] Example 20 Synthesis of 2,7-bis(2-cyclohexylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 20) Under a nitrogen atmosphere, 164 mg (1.20 mmol) of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) and 4 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 100 mL Schlenk tube and stirred under ice-cooling. Under ice-cooling, 1.20 mL (0.480 mmol) of the 0.4 M (2-cyclohexylethyl)magnesium bromide / THF solution prepared in Synthesis Example 8 was added, and the mixture was stirred at room temperature for 17 hours to prepare a zinc reagent solution.

[0346] 50.7 mg (0.120 mmol) of 2,7-dibromobiphenylene [1,2-b:5,6-b'] dithiophene (compound 3 in the publication) and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (Sigma-Aldrich) 8.78 mg (0.012 mmol) synthesized by the method described in WO2021 / 177417 were added thereto. The mixture was stirred at room temperature for 6.5 hours. The reaction mixture was ice-cooled, 1 M hydrochloric acid was added, and toluene was added for phase separation. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.

[0347] The resulting residue was purified by silica gel chromatography (solvent: toluene). The resulting solid was purified by circulating HPLC and recrystallized from hexane / toluene = 2 / 1. Further purification was performed by silica gel chromatography (solvent: hexane) and recrystallized from hexane to obtain 10.2 mg (yield 17%) of 2,7-bis(2-cyclohexylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 20) as an orange-red solid.

[0348] 1H NMR (CDCl3): δ=7.00 (d, J=7.2Hz, 2H), 6.69 (s, 2H), 6.63 (d, J=8.0Hz, 2H), 2.80 (t, J=7.6Hz, 4H), 1.78-1.64(m,10H),1.63-1.57(m,4H),1.38-1.28(m,2H),1.26-1.11(m,6H),0.99-0.90(m,4H).

[0349] Melting point: 174°C

[0350] [Chemical Formula 95] Example 21 Synthesis of 2-bromo-7-(2-cyclohexylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 21) Under a nitrogen atmosphere, 44.8 mg (0.120 mmol) of compound 19 synthesized in Example 19 and 5 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk reactor. The mixture was cooled to -78°C, and 0.224 mL (0.359 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added. The mixture was stirred at -78°C for 1 hour. After cooling to -78°C, 135 mg (0.416 mmol) of 1,2-dibromotetrachloroethane in 1 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 38.2 mg (yield 69%) of 2-bromo-7-(2-cyclohexylethyl)biphenyleno[1,2-b:5,6-b′]dithiophene (Compound 21) as an orange-red solid.

[0351] 1H NMR (CDCl3): δ=7.03(d,J=7.2Hz,2H),7.03(s,1H),6.71(s,1H),6.64(d,J=7.2Hz,1H),6.63(d ,J=7.2Hz,1H),2.80(t,J=7.6Hz,2H),1.75-1.57(m,7H),1.35-1.14(m,4H),0.98-0.90(m,2H).

[0352] Melting point: 142°C

[0353] [Chemical Formula 96] Example 22 Synthesis of 2-(2-cyclohexylethyl)hexylbiphenylene[1,2-b:5,6-b']dithiophene (Compound 22) Under a nitrogen atmosphere, 52.5 mg (0.385 mmol) of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) and 4 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk tube and stirred under ice cooling. Under ice cooling, 0.0679 mL (0.136 mmol) of a 2.0 M hexylmagnesium bromide / THF solution (Sigma-Aldrich) was added, and the mixture was stirred at 0°C for 20 minutes and at room temperature for 30 minutes to prepare a zinc reagent solution.

[0354] 30.8 mg (0.0679 mmol) of compound 21 synthesized in Example 21 and 6.10 mg (0.00834 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Sigma-Aldrich) were added thereto. The mixture was stirred at room temperature for 5 hours. The reaction mixture was ice-cooled, 1 M hydrochloric acid was added, and toluene was added for phase separation. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (solvent: toluene). The solid obtained was purified by circulating HPLC and purified by recrystallization from heptane to obtain 10.9 mg (yield 34%) of an orange-red solid of 2-(2-cyclohexylethyl)hexylbiphenyl[1,2-b:5,6-b']dithiophene (compound 22).

[0355] 1H NMR (CDCl3): δ=6.99(d,J=6.8Hz,2H),6.70(s,1H),6.69(s,1H),6.63(d,J=7.2Hz,2H),2.80(t,J=7.2Hz, 2H), 2.78 (t, J = 7.2Hz, 2H), 1.78-1.64 (m, 7H), 1.63-1.57 (m, 2H), 1.42-1.10 (m, 10H), 0.98-0.88 (m, 5H).

[0356] [Chemical Formula 97] Synthesis Example 9 Synthesis of (2-cyclopentylethyl)magnesium bromide Under a nitrogen atmosphere, 177 mg (7.27 mmol) of magnesium (Fujifilm Wako Pure Chemical Industries, Ltd., in the form of crumbs) was added to a 30 mL two-necked flask and stirred under vacuum. A 15 mL solution of 1.06 g (6.00 mmol) of (2-bromoethyl)cyclopentane synthesized in Synthesis Example 5 in THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. The solid was removed by filtration to obtain a 0.4 M (2-cyclopentylethyl)magnesium bromide / THF solution.

[0357] [Chemical Formula 98] Example 23 Synthesis of 2,7-bis(2-cyclopentylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 23) Under a nitrogen atmosphere, 182 mg (1.34 mmol) of zinc chloride (Fujifilm Wako Pure Chemical Industries, Ltd.) and 4 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk tube and stirred under ice-cooling. Under ice-cooling, 1.20 mL (0.480 mmol) of the 0.4 M (2-cyclopentylethyl)magnesium bromide / THF solution prepared in Synthesis Example 9 was added, and the mixture was stirred at room temperature for 15 hours to prepare a zinc reagent solution.

[0358] 50.9 mg (0.121 mmol) of 2,7-dibromobiphenylene [1,2-b:5,6-b'] dithiophene (compound 3 in the publication) and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (Sigma-Aldrich) 8.8 mg (0.012 mmol) synthesized by the method described in WO2021 / 177417 were added thereto. The mixture was stirred at room temperature for 25.5 hours. The reaction mixture was ice-cooled, 1 M hydrochloric acid was added, and toluene was added for phase separation. The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.

[0359] The resulting residue was purified by silica gel chromatography (solvent: toluene). The resulting solid was purified by recirculating HPLC and recrystallized from hexane / toluene = 4 / 1 to obtain 14.0 mg (yield 25%) of 2,7-bis(2-cyclopentylethyl)biphenyl[1,2-b:5,6-b']dithiophene (Compound 23) as an orange-red solid.

[0360] 1H NMR (CDCl3): δ=6.99 (d, J=7.6Hz, 2H), 6.70 (s, 2H), 6.63 (d, J=8.0Hz, 2H), 2.80 (t, J=7.6Hz, 4H) ,1.92-1.77(m,6H),1.75-1.69(m,4H),1.67-1.59(m,4H),1.57-1.48(m,4H),1.18-1.10(m,4H).

[0361] Melting point: 152°C

[0362] [Chemical Formula 99] Example 24 Evaluation of solubility Toluene or n-octane was added to the prescribed amounts of aromatic compounds obtained in Examples 1, 4, 5, 6, 7, 8, 9, 12, 13, 14, 15, 18, 19, 20, 22, and 23, respectively, to prepare film-forming compositions. The weight of each organic solvent required to completely dissolve the aromatic compound at room temperature (25°C) was measured, and the solubility (weight %) was calculated. The point at which complete dissolution was achieved was visually confirmed. The solubilities of the evaluated aromatic compounds are shown in Table 1.

[0363] Table 1 Solubility of the aromatic compound of the present invention Example 25 Preparation of an organic semiconductor layer-forming solution, an organic semiconductor layer, and an organic thin film transistor 1 In air, 1.74 mg of 2,8-bis(2-cyclohexylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 2) synthesized in Example 2 and 868 mg of toluene (Fujifilm Wako Pure Chemical Industries, pure grade) were added to a 10 ml sample tube. The mixture was heated to 50°C to dissolve the mixture, and then cooled to room temperature (25°C) to prepare a solution for forming an organic semiconductor layer. This solution remained in solution (Compound 2 concentration of 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 2 was suitable for film formation by drop casting and inkjet.

[0364] The obtained solution for forming an organic semiconductor layer was used to produce a bottom-gate-bottom-contact p-type organic thin film transistor. Table 2 shows the materials (constituent substrates) and film formation methods of the components.

[0365] Table 2 Components Base material Film production method substrate Glass - gate silver Vacuum evaporation Gate insulation layer Parylene C CVD Source / Drain Gold (W / L=500 / 100μm) Vacuum evaporation surface treatment agent Pentafluorobenzenethiol impregnation organic semiconductors Compound 2 Drop Casting The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 1.46 cm 2 / V·sec.

[0366] Example 26 Preparation of Organic Semiconductor Layer-Forming Solution, Organic Semiconductor Layer, and Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(2-cyclohexylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 8) synthesized in Example 8 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 8 concentration was 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 8 was suitable for film formation by drop casting and inkjet.

[0367] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0368] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 1.67 cm 2 / V·sec.

[0369] Example 27 Preparation of Organic Semiconductor Layer-Forming Solution, Organic Semiconductor Layer, and Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2,8-bis(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 10) synthesized in Example 10 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 10 concentration of 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 10 was suitable for film formation by drop casting and inkjet.

[0370] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0371] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 3.33 cm 2 / V·sec.

[0372] Example 28 Preparation of Organic Semiconductor Layer-Forming Solution, Organic Semiconductor Layer, and Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(2-cyclopentylethyl)-8-isobutylanthra[1,2-b:5,6-b']dithiophene (Compound 12) synthesized in Example 12 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 12 concentration of 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 12 was suitable for film formation by drop casting and inkjet.

[0373] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0374] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.22 cm 2 / V·sec.

[0375] Example 29 Preparation of an organic semiconductor layer-forming solution, an organic semiconductor layer, and an organic thin film transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(2-cyclopentylethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 13) synthesized in Example 13 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 13 concentration of 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 13 was suitable for film formation by drop casting and inkjet.

[0376] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0377] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 1.17 cm 2 / V·sec.

[0378] Example 30 Preparation of an organic semiconductor layer-forming solution, an organic semiconductor layer, and an organic thin film transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(2-cyclohexylethyl)-8-(2-cyclopentylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 14) synthesized in Example 14 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 14 concentration was 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 14 was suitable for film formation by drop casting and inkjet.

[0379] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0380] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.20 cm 2 / V·sec.

[0381] Example 31 Preparation of an Organic Semiconductor Layer-Forming Solution, an Organic Semiconductor Layer, and an Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(3-cyclohexylpropyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 18) synthesized in Example 18 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 18 concentration was 0.20 wt%) after being left at 25°C for 10 hours, confirming that Compound 18 was suitable for film formation by drop casting and inkjet.

[0382] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0383] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.48 cm 2 / V·sec.

[0384] Example 32 Preparation of an Organic Semiconductor Layer-Forming Solution, an Organic Semiconductor Layer, and an Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2,7-bis(2-cyclohexylethyl)biphenyleno[1,2-b:5,6-b']dithiophene (Compound 20) synthesized in Example 20 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 20 concentration was 0.2 wt%) after being left at 25°C for 10 hours, confirming that Compound 20 was suitable for film formation by drop casting and inkjet.

[0385] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0386] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.22 cm 2 / V·sec.

[0387] Example 33 Synthesis of 2-(3-cyclohexylpropyl)-8-butylanthra[1,2-b:5,6-b']dithiophene (Compound 24) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 40.5 mg (0.0821 mmol) of Compound 17 synthesized in Example 17, 5.70 mg (0.0250 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 23.7 mg (0.0508 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 33.6 mg (0.299 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 29.3 mg (0.287 mmol) of butylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture, 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.50 mL of water were added, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 21.8 mg (yield 56%) of 2-(3-cyclohexylpropyl)-8-butylanthra[1,2-b:5,6-b′]dithiophene (Compound 24) as a yellow solid.

[0388] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.7Hz,2H),7.15(s,2H),3.03(t,J=7.5Hz,2H),2.99(t,J=7.6H z,2H),1.87-1.80(m,4H),1.78-1.64(m,5H),1.54-1.45(m,2H),1.38-1.13(m,6H),1.00(t,J=7.4Hz,3H),1.02-0.88(m,2H).

[0389] (Compound 24)

[0390] [Chemical Formula 100] Example 34 Synthesis of 2-(3-cyclohexylpropyl)-8-pentylanthraquinone[1,2-b:5,6-b']dithiophene (Compound 25) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 40.7 mg (0.0825 mmol) of Compound 17 synthesized in Example 17, 6.20 mg (0.0280 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 26.7 mg (0.0572 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 38.4 mg (0.342 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 35.3 mg (0.304 mmol) of amylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture was added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.50 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 21.2 mg (yield 53%) of 2-(3-cyclohexylpropyl)-8-pentylanthraquinone[1,2-b:5,6-b′]dithiophene (Compound 25) as a yellow solid.

[0391] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.7Hz,2H),7.15(s,2H),3 .00(m,4H),1.88-1.80(m,4H),1.77-1.64(m,5H),1.46-1.13(m,10H),0.96-0.88(m,5H).

[0392] (Compound 25)

[0393] [Chemical Formula 101] Example 35 Synthesis of 2-(3-cyclohexylpropyl)-8-octylanthra[1,2-b:5,6-b']dithiophene (Compound 26) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 44.0 mg (0.0892 mmol) of Compound 17 synthesized in Example 17, 6.80 mg (0.0303 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 27.6 mg (0.0591 mmol) of Ruphos (Tokyo Chemical Industry, Ltd.), 41.0 mg (0.365 mmol) of potassium tert-butoxide (Tokyo Chemical Industry, Ltd.), and 51.2 mg (0.324 mmol) of octylboronic acid (Tokyo Chemical Industry, Ltd.). To this mixture, 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.50 mL of water were added, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using Celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 29.4 mg (yield 62%) of 2-(3-cyclohexylpropyl)-8-octylanthra[1,2-b:5,6-b′]dithiophene (Compound 26) as a yellow solid.

[0394] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,2H),3 .00(m,4H),1.88-1.79(m,4H),1.76-1.64(m,5H),1.50-1.13(m,16H),0.96-0.88(m,5H).

[0395] (Compound 26)

[0396] [Chemical Formula 102] Synthesis Example 10 Synthesis of 2-(3-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Under a nitrogen atmosphere, 30.0 mL (27.0 mmol) of 8.5% borane / THF solution (Tokyo Chemical Industry) and 2.00 mL (14.3 mmol) of allylcyclopentane (Tokyo Chemical Industry) were added to a 100 ml two-necked flask under ice cooling, and the mixture was stirred at 0°C for 50 minutes and at room temperature for 1.5 hours. Under ice cooling, 4.0 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 sodium bicarbonate aqueous 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 (3-cyclopentylpropyl)boric acid.

[0397] Under a nitrogen atmosphere, the obtained boronic acid was added to a 200 mL two-necked flask. 2.09 g (17.7 mmol) of pinacol (Tokyo Chemical Industry) and 15.0 mL of diethyl ether (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added, and the mixture was stirred at room temperature. 2.34 g (19.4 mmol) of magnesium sulfate (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at room temperature for 4 hours. The solid was removed by vacuum filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: toluene) to obtain 1.03 g (yield 27%) of 2-(3-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless liquid.

[0398] (2-(3-Cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

[0399] [Chemical Formula 103] Example 36 Synthesis of 2-(3-cyclopentylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 27) Under a nitrogen atmosphere, 261 mg of a mixture of 2-bromoanthra[1,2-b:5,6-b']dithiophene (compound 22 in the publication) and 2,8-dibromoanthra[1,2-b:5,6-b']dithiophene (compound 20 in the publication) synthesized by the method described in WO2021 / 177417, 32.3 mg (0.144 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 133 mg (0.285 mmol) of Ruphos (Tokyo Chemical Industry), and 267 mg (2.38 mmol) of potassium tert-butoxide (Tokyo Chemical Industry) were added to a 200 mL Schlenk tube. To this was added 20 mL of a toluene solution (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) of 534 mg (2.70 mmol) of 2-(2-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in Synthesis Example 10) and 2.0 mL of water, and the mixture was stirred at 80°C for 4 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 recirculating HPLC and purified by recrystallization from heptane to obtain 82.8 mg of 2-(3-cyclopentylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 27) as a yellow solid.

[0400] 1H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=8.8Hz,1H),7.87(d,J=8.7Hz,1H),7.82(d,J=8.7Hz,1H),7.73(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(t,J=7.3Hz,2H),1.89-1.78(m,5H),1.63-1.45(m,6H),1.16-1.08(m,2H).

[0401] Melting point: 136°C (Compound 27)

[0402] [Chemical Formula 104] Example 37 Synthesis of 2,8-bis(3-cyclopentylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 28) The remaining components obtained by the recycle HPLC purification in Example 36 were purified by recrystallization from heptane to obtain 12.5 mg of 2,8-bis(3-cyclopentylpropyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 28) as a yellow solid.

[0403] 1 H NMR (CDCl3): δ=8.59(s,2H),7.85(d,J=8.8Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,2H),3.02(t ,J=7.2Hz,4H),1.88-1.76(m,10H),1.65-1.44(m,12H),1.38-1.10(m,12H),1.15-1.09(m,4H).

[0404] Melting point: 143°C (Compound 28)

[0405] [Chemical Formula 105] Example 38 Synthesis of 2-bromo-8-(3-cyclopentylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 29) Under a nitrogen atmosphere, 80.2 mg (0.193 mmol) of compound 27 synthesized in Example 36 and 5.0 mL of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 mL Schlenk reactor. The mixture was cooled to -78°C, and 1.00 mL (1.60 mmol) of 1.6 M n-butyllithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added. The mixture was stirred at -78°C for 2 hours. After cooling to -78°C, 719 mg (2.21 mmol) of 1,2-dibromotetrachloroethane was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 79.2 mg (82% yield) of 2-bromo-8-(3-cyclopentylpropyl)anthra[1,2-b:5,6-b']dithiophene (Compound 29) as a yellow solid.

[0406] 1 H NMR (CDCl3): δ=8.59(s,1H),8.52(s,1H),7.86(d,J=8.7Hz,1H),7.84(d,J=8.7Hz,1H),7.73(d,J=8.7Hz,1H),7.68(d,J =8.9Hz,1H),7.46(s,1H),7.16(s,1H),3.01(t,J=7.4Hz,2H),1.89-1.76(m,7H),1.66-1.44(m,6H),1.18-1.07(m,2H).

[0407] (Compound 29)

[0408] [Chemical Formula 106] Example 39 Synthesis of 2-(3-cyclopentylpropyl)-8-pentylanthraquinone[1,2-b:5,6-b']dithiophene (Compound 30) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 34.0 mg (0.0709 mmol) of compound 29 synthesized in Example 38, 5.60 mg (0.0249 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 23.0 mg (0.0493 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 32.8 mg (0.292 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 28.4 mg (0.245 mmol) of amylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture was added 4.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.40 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by recirculating HPLC and recrystallized from heptane to obtain 12.1 mg (yield 36%) of 2-(3-cyclopentylpropyl)-8-pentylanthraquinone[1,2-b:5,6-b′]dithiophene (Compound 30) as a yellow solid.

[0409] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.8Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,2H),3.01(t ,J=7.5Hz,4H),1.88-1.75(m,8H),1.63-1.38(m,9H),1.14-1.09(m,2H),0.94(t,J=7.1Hz,3H).

[0410] (Compound 30)

[0411] [Chemical Formula 107] Example 40 Synthesis of 2-(3-cyclopentylpropyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 31) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 35.3 mg (0.0736 mmol) of compound 29 synthesized in Example 38, 4.80 mg (0.0213 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 20.6 mg (0.0441 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 35.1 mg (0.313 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 34.6 mg (0.266 mmol) of hexylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture was added 4.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.40 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 10.1 mg (yield 28%) of 2-(3-cyclopentylpropyl)-8-hexylanthra[1,2-b:5,6-b′]dithiophene (Compound 31) as a yellow solid.

[0412] 1 H NMR (CDCl3): δ=8.59(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,2H),3.02(t,J=7.4Hz ,4H),1.88-1.75(m,7H),1.62-1.43(m,8H),1.40-1.31(m,4H),1.16-1.07(m,2H),0.92(t,J=6.8Hz,3H).

[0413] (Compound 31)

[0414] [Chemical Formula 108] Example 41 Synthesis of 2-(cyclohexylmethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 32) Under a nitrogen atmosphere, a 100 mL Schlenk tube was charged with 411 mg of a mixture of 2-bromoanthra[1,2-b:5,6-b']dithiophene (Compound 22 in the publication) and 2,8-dibromoanthra[1,2-b:5,6-b']dithiophene (Compound 20 in the publication), synthesized by the method described in WO2021 / 177417, 88.7 mg (0.395 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 378 mg (0.285 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 573 mg (4.03 mmol) of cyclohexylmethylboronic acid (Fujifilm Wako Pure Chemical Industry Co., Ltd.), and 476 mg (4.24 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.). To this mixture, 30 mL of toluene and 1.5 mL of water were added, and the mixture was stirred at 80°C for 20 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 recirculating HPLC and purified by recrystallization from heptane to obtain 171 mg of 2-(cyclohexylmethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 32) as a yellow solid.

[0415] 1 H NMR (CDCl3): δ=8.70(s,1H),8.62(s,1H),7.89(d,J=8.8Hz,1H),7.87(d,J=8.7Hz,1H),7.82(d,J=8.8Hz,1H),7.73(d,J=8.7Hz,1H),7.53(d,J=4 .9Hz,1H),7.49(d,J=5.1Hz,1H),7.14(s,1H),2.08(d,J=7.1Hz,2H),1.8 9-1.73(m,2H),1.77-1.67(m,4H),1.33-1.18(m,3H),1.10-1.01(m,2H).

[0416] Melting point: 137°C (Compound 32)

[0417] [Chemical Formula 109] Example 42 Synthesis of 2,8-bis(cyclohexylmethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 33) The remaining components obtained by the recycle HPLC purification in Example 41 were purified by recrystallization from heptane to obtain 23.8 mg of 2,8-bis(cyclohexylmethyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 33) as a yellow solid.

[0418] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.13(s,2H),2.88( d,J=6.9Hz,4H),1.89-1.82(m,4H),1.77-1.67(m,8H),1.33-1.17(m,6H),1.10-1.00(m,4H).

[0419] Melting point: 220℃ (Compound 33)

[0420] [Chemical Formula 110] Example 43 Synthesis of 2-bromo-8-(cyclohexylmethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 34) Under a nitrogen atmosphere, 152 mg (0.394 mmol) of compound 32 synthesized in Example 41 and 5.0 ml of THF (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were added to a 50 ml Schlenk reactor. The mixture was cooled to -78°C, 0.80 mL (1.30 mmol) of 1.6 M n-butyl lithium (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at -78°C for 3 hours. After cooling to -78°C, 445 mg (1.37 mmol) of 1,2-dibromotetrachloroethane was added, and the mixture was stirred while warming to room temperature. 1 M hydrochloric acid was added, and the solid was filtered and washed with water and methanol to obtain 163 mg (88% yield) of 2-bromo-8-(cyclohexylmethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 34) as a yellow solid.

[0421] 1 H NMR (CDCl3): δ=8.59(s,1H),8.54(s,1H),7.86(d,J=8.8Hz,1H),7.85(d,J=8.8Hz,1H),7.73(d,J=8.7Hz,1H),7.69(d,J=8.9Hz,1 H),7.68(s,1H),7.14(s,1H),2.89(d,J=7.1Hz,2H),1.89-1.82(m,2H),1.76-1.67(m,4H),1.34-1.17(m,3H),1.10-1.01(m,2H).

[0422] (Compound 34)

[0423] [Chemical Formula 111] Example 44 Synthesis of 2-(cyclohexylmethyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 35) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 40.6 mg (0.0872 mmol) of compound 34 synthesized in Example 43, 6.70 mg (0.0298 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 27.7 mg (0.0594 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 33.9 mg (0.302 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 34.0 mg (0.262 mmol) of hexylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture was added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.50 mL of water, and the mixture was stirred at 80°C for 3.5 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 21.5 mg (yield 52%) of 2-(cyclohexylmethyl)-8-hexylanthra[1,2-b:5,6-b′]dithiophene (Compound 35) as a yellow solid.

[0424] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,1H),7.13(s,1H),3.02(t,J=7.4Hz,2H),2.88(d,J=7.0Hz, 2H),1.88-1.79(m,4H),1.76-1.66(m,4H),1.52-1.43(m,2H),1.40-1. 36(m,4H),1.35-1.19(m,3H),1.10-1.00(m,2H),0.92(t,J=6.9Hz,3H).

[0425] Melting point: 133°C (Compound 35)

[0426] [Chemical Formula 112] Example 45 Synthesis of 2-(cyclohexylmethyl)-8-octylanthra[1,2-b:5,6-b']dithiophene (Compound 36) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 43.6 mg (0.0937 mmol) of compound 34 synthesized in Example 43, 7.80 mg (0.0347 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 34.5 mg (0.0739 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 33.6 mg (0.300 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 44.3 mg (0.280 mmol) of octylboronic acid (Tokyo Chemical Industry Co., Ltd.). To this mixture, 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.50 mL of water were added, and the mixture was stirred at 80°C for 4 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), 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 obtained solid was purified by circulating HPLC and recrystallized from heptane to obtain 30.6 mg (yield 65%) of 2-(cyclohexylmethyl)-8-octylanthra[1,2-b:5,6-b′]dithiophene (Compound 36) as a yellow solid.

[0427] 1 H NMR (CDCl3): δ=8.58(s,2H),7.84(d,J=8.7Hz,2H),7.70(d,J=8.8Hz,2H),7.15(s,1H),7.12(s,1H),3.02(t,J=7. 5Hz, 2H), 2.88 (d, J = 7.1Hz, 2H), 1.88-1.70 (m, 8H), 1.49-1.20 (m, 13H), 1.09-1.00 (m, 2H), 0.90 (t, J = 6.6Hz, 3H).

[0428] Melting point: 130°C (Compound 36)

[0429] [Chemical Formula 113] Example 46 Synthesis of 2-(2-cyclohexylethyl)-8-phenylanthraquinone[1,2-b:5,6-b']dithiophene (Compound 37) Under a nitrogen atmosphere, 32.9 mg (0.0686 mmol) of compound 3 synthesized in Example 3, 4.80 mg (0.021 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 19.9 mg (0.0426 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 27.5 mg (0.245 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 25.9 mg (0.212 mmol) of phenylboronic acid (Tokyo Chemical Industry Co., Ltd.) were added to a 50 mL Schlenk tube. To this mixture were added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 4 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene). The obtained solid was purified by circulating HPLC and recrystallized from toluene / heptane to obtain 19.2 mg (yield 58%) of 2-(2-cyclohexylethyl)-8-phenylanthra[1,2-b:5,6-b′]dithiophene (Compound 37) as a yellow solid.

[0430] 1 H NMR (CDCl3): δ=8.68(s,1H),8.61(s,1H),7.90-7.78(m,5H),7.73(d,J=8.8Hz,1H),7.70(s,1H),7.49-7.45(m,2H),7.38-7 .34(m,1H),7.17(s,1H),3.04(t,J=7.5Hz,2H),1.85-1.66(m,7H),1.47-1.37(m,1H),1.32-1.14(m,3H),1.05-0.96(m,2H).

[0431] Melting point: 229°C (Compound 37)

[0432] [Chemical formula 114] Example 47 Synthesis of 2-(2-cyclohexylethyl)-8-(p-tolyl)anthra[1,2-b:5,6-b']dithiophene (Compound 38) Under a nitrogen atmosphere, 34.3 mg (0.0715 mmol) of compound 3 synthesized in Example 3, 5.40 mg (0.0241 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 22.3 mg (0.0478 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 28.5 mg (0.254 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 31.6 mg (0.232 mmol) of 4-methylphenylboronic acid (Tokyo Chemical Industry Co., Ltd.) were added to a 50 mL Schlenk tube. To this mixture were added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene). The obtained solid was purified by circulating HPLC and recrystallized from toluene / heptane to obtain 22.1 mg (yield 62%) of 2-(2-cyclohexylethyl)-8-(p-tolyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 38) as a yellow solid.

[0433] 1 H NMR (CDCl3): δ=8.66(s,1H),8.60(s,1H),7.89-7.86(m,2H),7.77(d,J=8.8Hz,1H),7.73-7.69(m,3H),7.65(s,1H),7.28(m,2H ),7.16(s,1H),3.03(t,J=7.8Hz,2H),2.42(s,3H),1.85-1.66(m,7H),1.48-1.37(m,1H),1.32-1.14(m,3H),1.05-0.96(m,2H).

[0434] Melting point: 240℃ (Compound 38)

[0435] [Chemical Formula 115] Example 48 Synthesis of 2-(2-cyclohexylethyl)-8-(4-hexylphenyl)anthra[1,2-b:5,6-b']dithiophene (Compound 39) Under a nitrogen atmosphere, 40.0 mg (0.0834 mmol) of compound 3 synthesized in Example 3, 5.00 mg (0.0223 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 20.3 mg (0.0435 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 37.0 mg (0.330 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 58.4 mg (0.283 mmol) of 4-hexylphenylboronic acid (Tokyo Chemical Industry Co., Ltd.) were added to a 50 mL Schlenk tube. To this mixture were added 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water, and the mixture was stirred at 80°C for 4 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene). The obtained solid was purified by circulating HPLC and recrystallized from toluene / heptane to obtain 18.7 mg (yield 39%) of 2-(2-cyclohexylethyl)-8-(4-hexylphenyl)anthra[1,2-b:5,6-b′]dithiophene (Compound 39) as a yellow solid.

[0436] 1 H NMR (CDCl3): δ=8.67(s,1H),8.60(s,1H),7.89-7.86(m,2H),7.77(d,J=8.8Hz,1H),7.73-7.70(m,3H),7.65(s,1H),7.29(m,2H),7.1 6(s,1H),3.03(t,J=7.8Hz,2H),2.67(t,J=7.6Hz,2H),1.87-1.63(m,9H),1.44-1.17(m,10H),1.05-0.95(m,2H),0.93-0.89(m,3H).

[0437] Melting point: 196°C (Compound 39)

[0438] [Chemical Formula 116] Example 49 Preparation of an Organic Semiconductor Layer-Forming Solution, an Organic Semiconductor Layer, and an Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(3-cyclohexylpropyl)-8-pentylanthraquino[1,2-b:5,6-b']dithiophene (Compound 25) synthesized in Example 34 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 25 concentration was 0.2 wt%) after being left at 25°C for 10 hours, confirming that Compound 25 was suitable for film formation by drop casting and inkjet.

[0439] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0440] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 1.18 cm 2 / V·sec.

[0441] Example 50 Preparation of an organic semiconductor layer forming solution, an organic semiconductor layer, and an organic thin film transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(3-cyclopentylpropyl)-8-hexylanthra[1,2-b:5,6-b']dithiophene (Compound 31) synthesized in Example 40 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 31 concentration of 0.2 wt%) after being left at 25°C for 10 hours, confirming that Compound 31 was suitable for film formation by drop casting and inkjet.

[0442] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0443] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.49 cm 2 / V·sec.

[0444] Synthesis Example 11 Synthesis of 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane Under a nitrogen atmosphere, 52.0 mL (46.8 mmol) of 8.5% borane / THF solution (Tokyo Chemical Industry) and 5.60 mL (23 mmol) of 4-n-octylstyrene (Tokyo Chemical Industry) were added to a 100 ml two-necked flask under ice cooling, and the mixture was 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 sodium bicarbonate aqueous solution were added for phase separation. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to synthesize (4-octylphenylethyl)boric acid.

[0445] Under a nitrogen atmosphere, the obtained boronic acid was added to a 300 mL eggplant-shaped flask. 5.78 g (48.7 mmol) of pinacol (Tokyo Chemical Industry) and 40.0 mL of diethyl ether (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) were also added, and the mixture was stirred at room temperature. 6.09 g (50.6 mmol) of magnesium sulfate (Fujifilm Wako Pure Chemical Industries, Ltd.) was added to the mixture, and the mixture was stirred at room temperature for 4 hours. The solid was removed by vacuum filtration, 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 (yield 29%) of a colorless liquid of 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane.

[0446] 1 H NMR (CDCl3): δ=7.12(d,J=8.1Hz,2H),7.07(d,J=8.1Hz,2H),2.72(t,J=8.1Hz,2H),2.56(t,J=7.6Hz,2 H), 1.62-1.55 (m, 2H), 1.34-1.26 (m, 10H), 1.23 (s, 12H), 1.14 (t, J = 8.3Hz, 2H), 0.89 (t, J = 6.7Hz, 3H). 4,4,5,5-Tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane

[0447] [Chemical Formula 117] Example 51 Synthesis of 2-(2-cyclohexylethyl)-8-(4-octylphenylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 40) Under a nitrogen atmosphere, a 50 mL Schlenk tube was charged with 37.7 mg (0.0786 mmol) of compound 3 synthesized in Example 3, 6.20 mg (0.0276 mmol) of palladium(II) acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 25.8 mg (0.0553 mmol) of Ruphos (Tokyo Chemical Industry Co., Ltd.), 32.5 mg (0.290 mmol) of potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), and 103 mg (0.299 mmol) of 4,4,5,5-tetramethyl-2-(4-octylphenylethyl)-1,3,2-dioxaborolane synthesized in Synthesis Example 11. 5.0 mL of toluene (Fujifilm Wako Pure Chemical Industries, Ltd., dehydrated grade) and 0.5 mL of water were added, and the mixture was stirred at 80°C for 20 hours. The reaction mixture was cooled to room temperature, insoluble matter was removed using celite (Fujifilm Wako Pure Chemical Industries, Ltd.), and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene / hexane = 1 / 2). The resulting solid was purified by recirculating HPLC and recrystallized from heptane to obtain 25.8 mg (yield 53%) of 2-(2-cyclohexylethyl)-8-(4-octylphenylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 40) as a yellow solid.

[0448] 1 H NMR (CDCl3): δ=8.59(s,2H),7.85(d,J=8.8Hz,1H),7.84(dd,J=8.8Hz,1H),7.70(d,J=8 .8Hz,1H),7.69(d,J=8.7Hz,1H),7.19-7.12(m,6H),3.31(t,J=7.4Hz,2H),3.11(t,J=8 .6Hz,2H),3.03(t,J=7.2Hz,2H),2.59(t,J=7.6Hz,2H),1.85-1.81(m,2H),1.76-1.58( m,7H),1.47-1.37(m,1H),1.36-1.16(m,13H),1.05-0.95(m,2H),0.89(t,J=6.5Hz,3H).

[0449] Melting point: 161°C (Compound 40)

[0450] [Chemical Formula 118] Example 52 Preparation of an Organic Semiconductor Layer-Forming Solution, an Organic Semiconductor Layer, and an Organic Thin Film Transistor A solution for forming an organic semiconductor layer was prepared by the same method as in Example 25, except that 2-(2-cyclohexylethyl)-8-(4-octylphenylethyl)anthra[1,2-b:5,6-b']dithiophene (Compound 40) synthesized in Example 51 was used. This solution for forming an organic semiconductor layer remained in a solution state (Compound 40 concentration was 0.2 wt%) after being left at 25°C for 10 hours, confirming that Compound 40 was suitable for film formation by drop casting and inkjet.

[0451] Using the obtained solution for forming an organic semiconductor layer, and employing the materials and film-forming method of each component shown in Example 25, a bottom-gate-bottom-contact p-type organic thin-film transistor was produced.

[0452] The transfer characteristics of the transistor were evaluated and the hole carrier mobility was 0.66 cm 2 / V·sec.

[0453] Comparative Example 1 (Preparation of Solution for Forming Organic Semiconductor Layer) In air, 0.44 mg of 2,7-diphenyl[1]benzothiophene[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. The mixture was heated to 50°C and allowed to cool to room temperature (25°C). Solid precipitation was confirmed. Due to its low solubility, this compound was found to be unsuitable for film formation by drop casting or inkjet.

[0454] Comparative Example 2 (Preparation of Solution for Forming Organic Semiconductor Layer) In air, a 10 ml sample tube was filled with 2,8-dioctylanthra[1,2-b:5,6-b']dithiophene synthesized by the method described in WO2021 / 177417 to prepare a solution for forming an organic semiconductor layer by the same method as in Example 25. The solution for forming an organic semiconductor layer remained in a solution state (0.20 wt%) after standing at 25°C for 10 hours, confirming that the compound was suitable for film formation by drop casting and inkjet.

[0455] (Fabrication of organic semiconductor layers and organic thin-film transistors) An attempt was made to produce a bottom-gate / bottom-contact p-type organic thin film transistor using this organic semiconductor layer-forming solution and the materials and film-forming method described in Example 25. However, no thin film was formed, and a bottom-gate / bottom-contact p-type organic thin film transistor could not be produced.

[0456] Comparative Example 3 For 2,8-di(2-phenylethyl)anthraquinone[1,2-b:5,6-b']dithiophene (compound 10 in the publication), 2-(2-phenylethyl)anthraquinone[1,2-b:5,6-b']dithiophene (compound 15 in the publication), and 2-(2-(4-methylphenyl)ethyl)anthraquinone[1,2-b:5,6-b']dithiophene (compound 16 in the publication) synthesized by the method described in WO2021 / 177417, the solubility in octane was evaluated by the method of Example 24, and the results were all less than 0.10% by weight, confirming that the compounds were compounds with low solubility in octane. Industrial applicability

[0457] The aromatic compound of the present invention can provide high carrier mobility and is excellent in heat resistance and solubility, and therefore is expected to be suitable as a material for semiconductor devices such as organic thin film transistors. Description of Reference Numerals

[0458] 1: Organic semiconductor layer 2:Substrate 3: Gate 4: Gate insulation layer 5: Source 6: Drain 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 any one of the following formulas (1-I) or (1-II), [Chemical Formula 1] in, Ar represents a single ring or 2 to 6 condensed rings; X 1 、X 2 Each independently represents a member selected from oxygen, sulfur, selenium, NR 3 and CR 4 =CR 5 One of the groups; Y 1 、Y 2 Each independently represents CR 6 or any of the nitrogen atoms; R 1 ~R 6 Each independently represents one of 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, or a group represented by the following formula (2), and R 1 ~R 6 At least one of them is a group represented by the following formula (2), [Chemical Formula 2] wherein k and m are independently 0 or 1, n is an integer from 1 to 8, and l is an integer from 1 to 20; 1 ~Z 5 Each occurrence of "" is the same or different and represents one selected from the group consisting of a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms.

2. The aromatic compound according to claim 1, wherein R 1 ~R 6 In, only R 1 and R 2 Either or only R 1 and R 2 Both are groups represented by the above-mentioned formula (2).

3. The aromatic compound according to claim 1, wherein The aromatic compound represented by the formula (1-I) or (1-II) is a compound represented by one selected from the group consisting of the following formulas (3-1) to (3-6), [Chemical Formula 3] Among them, X 3 、X 4 、X 5 Each independently represents a group selected from oxygen atom, sulfur atom, selenium atom, single bond, NR 17 and CR 18 =CR 19 One of the groups consisting of 7 ~R 10 Among the combinations of two adjacent components in , only one group constitutes the following formula (4), and in the combination of R 11 ~R 14 Of the two adjacent combinations in the formula (4-2), only one group constitutes the following formula (4-2), and each forms a 5-membered ring or a 6-membered ring; R that does not constitute the following formula (4) and the following formula (4-2) 7 ~R 14 and R 15 ~R 19 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2). [Chemical Formula 4] Among them, X 6 represents an atom selected from oxygen, sulfur, selenium, CR 21 =CR 22 and NR 23 One of the groups; Y 3 Indicates CR 24 or any of the nitrogen atoms; R 21 ~R 24 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2); R 20 is a group represented by the formula (2), [Chemical Formula 5] Among them, X 6 、Y 3 Represents X in the formula (4) 6 、Y 3 Same meaning, R 20b 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2).

4. The aromatic compound according to claim 3, wherein The aromatic compound represented by the formula (1-I) or (1-II) is a compound represented by the formula (3-1) or (3-2).

5. The aromatic compound according to claim 3, wherein The formula (4-2) is the following formula (4-3), [Chemical Formula 6] Among them, X 6 、Y 3 Represents X in the formula (4) 6 、Y 3 Same meaning, R 20c It 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms.

6. The aromatic compound according to claim 3, wherein The formula (4-2) is the following formula (4-4), [Chemical Formula 7] Among them, X 6 、Y 3 Represents X in the formula (4) 6 、Y 3 Same meaning, R 20d It is a group represented by the above formula (2).

7. The aromatic compound according to claim 1, wherein The aromatic compound represented by the formula (1-I) or (1-II) is a compound represented by the following formula (5) or the following formula (5-2), [Chemical Formula 8] Among them, in the 25 ~R 28 Among the combinations of two adjacent components in , only one group constitutes the following formula (6), and in the combination of R 29 ~R 32 Of the two adjacent combinations in the formula (6-2), only one group constitutes the following formula (6-2) and forms a 5-membered ring or a 6-membered ring respectively; R that does not constitute the following formula (6) and the following formula (6-2) 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2). [Chemical Formula 9] Among them, X 7 represents oxygen atoms, sulfur atoms, selenium atoms, CR 34 =CR 35 , or NR 36 ; Y 4 Indicates CR 37 or any of the nitrogen atoms; R 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and a group represented by formula (2); R 33 is a group represented by the formula (2), [Chemical Formula 10] Among them, X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2).

8. The aromatic compound according to claim 7, wherein The formula (6-2) is the following formula (6-3), [Chemical Formula 11] Among them, X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, R 33c It 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, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, and an aryl group having 4 to 26 carbon atoms.

9. The aromatic compound according to claim 7, wherein The formula (6-2) is the following formula (6-4), [Chemical Formula 12] Among them, X 7 、Y 4 Represents X in the above formula (6) 7 、Y 4 Same meaning, R 33d It is a group represented by the above formula (2).

10. The aromatic compound according to claim 1, wherein The aromatic compound represented by the formula (1-I) or (1-II) is a compound represented by one selected from the group consisting of the following formulas (7-1) to (7-6), [Chemical Formula 13] Among them, X 8 、X 9 Each independently represents an oxygen atom, a sulfur atom, a selenium atom, or NR 44 ; Y 5 、Y 6 Each independently represents CR 45 or nitrogen atom; R 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, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a dienyl group having 4 to 22 carbon atoms, a dialkynyl group having 4 to 22 carbon atoms, an aryl group having 4 to 26 carbon atoms, and the group represented by formula (2); R 38 and R 41 At least one of them is a group represented by the formula (2).

11. The aromatic compound according to claim 10, wherein R 38 and R 41 are independently selected from the group consisting of a group represented by formula (2), a hydrogen atom and a fluorine atom, R 39 、R 40 、R 42 ~R 45 、R 71 and R 72 A hydrogen atom.

12. The aromatic compound according to claim 10, wherein R 38 and R 41 is a group represented by the formula (2), R 39 、R 40 、R 42 ~R 45 、R 71 and R 72 A hydrogen atom. 13 . A solution for forming an organic semiconductor layer, comprising the aromatic compound according to claim 1 . 14 . An organic semiconductor layer comprising the aromatic compound according to claim 1 . 15 . An organic thin film transistor comprising the aromatic compound according to claim 1 .

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