JP6866618B2 - Inkjet ink for forming organic semiconductor thin films - Google Patents

Description

The present invention relates to an inkjet ink for forming an organic semiconductor thin film that exhibits excellent field effect mobility and can suppress variations in field effect mobility.

Source electrodes, drain electrodes and gate electrodes, gate insulating film layers, and transistors on which organic semiconductor thin films are laminated are expected to be used in liquid crystal displays, electronic paper, electroluminescence (EL) display devices, RF-ID tags, etc. ing. Transistors for these applications have conventionally been manufactured by forming electrodes and semiconductor layers in a dry process such as a vapor deposition method or a sputtering method. In recent years, there has been a strong demand for higher density, smaller size, and improved productivity, and we are studying a method for manufacturing transistors that does not require large-scale and expensive vacuum equipment, which is indispensable when the vapor deposition method is adopted. However, recently, wet processes such as printing methods, which can suppress energy consumption at lower temperatures, increase productivity, and can be made denser and smaller, are attracting attention.

In particular, with respect to the semiconductor layer, the development of a method for forming the semiconductor layer by a wet process has been actively carried out in recent years. In order to put it into practical use, it is required that the variation in the field effect mobility is small in addition to the excellent field effect mobility, but there are not many reports on a method for forming an organic semiconductor thin film that achieves both of these. In particular, there are few reports on devices in which an organic semiconductor thin film is formed by the inkjet method, which is one of the processes that can be mass-produced.
For example, in Patent Document 1, a low molecular weight organic semiconductor is subjected to a spin coating method, a casting method, a dip method, an inkjet method, a doctor blade method, a gravure printing method, a screen printing method, an offset printing method, a letterpress printing method, and a reverse printing method. In a thin film formed by an organic semiconductor thin film by a known wet film forming method such as a method, a microcontact printing method, a wire bar coating method, a spray coating method, or a dispensing method, it is easy to obtain a film having high mobility and small variation in mobility. Although there is a description that it can be formed, there is no detailed description regarding the composition of the inkjet ink, and the characteristics of the transistor in which the organic semiconductor thin film is formed by the inkjet method are not described in the examples. Further, also in Patent Document 2, using a low molecular weight organic semiconductor, a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, High in thin films in which organic semiconductor thin films are produced by coating methods such as spray coating, screen printing, flexo printing, offset printing, inkjet printing, dispenser printing, microcontact printing, nozzle coating, and capillary coating. There is a description that a film having a small variation in mobility can be easily formed by the mobility, but there is no detailed description about the composition of the inkjet ink, and the characteristics of the transistor formed by the inkjet method to form the organic semiconductor thin film are the examples. Is not listed in. Further, in Patent Document 3, a composition for forming an organic semiconductor film of an organic transistor for inkjet printing or flexo printing using a low molecular weight organic semiconductor is mentioned as a claim, and further, an organic semiconductor is described by an inkjet method. The characteristics of the transistor forming the thin film are described in the examples, and although the variation in the field effect mobility is less than 30%, the value of the field effect mobility remains as low as ^{0.2 cm 2 / Vs.} There is.

WO2014-03708A Japanese Unexamined Patent Publication No. 2012-39103 Japanese Patent Application No. 2014-701262

As described above, it is difficult to achieve both excellent field effect mobility and small variation in a semiconductor device in which an organic semiconductor thin film is formed by an inkjet method, which is one of the processes that can be mass-produced.

Therefore, an object of the present invention is an inkjet ink for forming an organic semiconductor thin film which exhibits excellent field effect mobility and has a small variation in field effect mobility, and a thin film transistor having an organic semiconductor thin film made of the ink. The purpose is to provide an electronic device composed of transistors.

As a result of diligent studies in view of the above-mentioned actual conditions, the present inventors have been excellent in using an organic semiconductor thin film transistor forming inkjet ink containing a specific organic semiconductor material and an organic solvent having an appropriate boiling point and surface tension. We have found that an organic semiconductor thin film, a thin film transistor, and an electronic device including the thin film transistor, which show the field effect mobility and have a small variation in the field effect mobility, are formed, and have completed the present invention. That is, the present inventors have found that the above problems can be solved by the following configuration.

1. 1. An inkjet ink for forming an organic semiconductor thin film, which is an organic semiconductor compound represented by the general formula (1-1), an organic semiconductor compound represented by the general formula (2-1), and represented by the general formula (3-1). At least one organic semiconductor compound selected from the organic semiconductor compounds represented by the general formula (4-1), a boiling point of 180 ° C. or higher and 250 ° C. or lower, and a surface tension of 20 mN / m or higher and 38 mN /. An inkjet ink for forming an organic semiconductor thin film containing an organic solvent of m or less.

(In the formula, R ₁₁ and R ₁₂ are groups represented by either (I) or (I-II) below, but at least one is (I).
(I)
A group of the general formula (1-2) or (1-3).

(Ar ₁₁ may have an aromatic hydrocarbon group or a hetero-aromatic _{group which may have a substituent, Ar 12} may have an aromatic hydrocarbon group or a substituent which may have a substituent. groups, R 1 _'is hydrogen atom, trialkylsilyl group having an alkyl group of 1 to 4 carbon atoms, having 1 to 20 carbon atoms alkyl group, an aromatic optionally having a substituent hydrocarbon group or a heteroaromatic It is a family group.)
(I-II)
Alkyl group having 2 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkyl group having 2 to 20 carbon atoms having a halogen atom, alkoxyalkyl group having 3 to 20 carbon atoms, alkylsulfanylalkyl having 3 to 20 carbon atoms Group, alkylaminoalkyl group with 3 to 20 carbon atoms, aromatic hydrocarbon group or heteroaromatic group, alkyl group with 1 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, carbon number having halogen atom An aromatic hydrocarbon group having an alkyl group of 1 to 20, an alkoxyalkyl group having 3 to 20 carbon atoms, an alkylsulfanyl alkyl group having 3 to 20 carbon atoms, or an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent or It is a group selected from complex aromatic groups. )

(In the formula, R ₂₁ is a group of any of (II-I) and R ₂₂ is a group selected from any of the groups of (II-II).
(II-I)
A group of the general formula (2-2) or (2-3).

(Ar ₂₁ is an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 18 carbon atoms as a substituent, and the aromatic hydrocarbon group or the heteroaromatic group has a monocyclic or ring number. is a polycyclic 2 or 3 groups, Ar ₂₂ is an aromatic be substituted hydrocarbon group or an optionally substituted heteroaromatic group, R 2 _'is a hydrogen atom, the number of carbon atoms It is an aromatic hydrocarbon group or a heteroaromatic group which may have 1 to 20 alkyl groups and substituents.)
(II-II)
It is a group selected from a hydrogen atom, a methyl group, a cyano group, a fluoro group, and a trifluoromethyl group. )

(In the formula, R _{301 to} R ₃₁₂ are hydrogen atoms or arbitrary substituents, R ₃₀₁ and R ₃₁₂ are the same or different, R ₃₀₂ and R ₃₁₁ are the same or different, and R ₃₀₃ and R ₃₁₀ are the same. Or different, R ₃₀₄ and R ₃₀₉ are the same or different, R ₃₀₅ and R ₃₀₈ are the same or different, R ₃₀₆ and R ₃₀₇ are the same or different, but R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ and R ₃₀₃ and R. _{Of the six combinations of 310} , R ₃₀₄ and R ₃₀₉ , R ₃₀₅ and R ₃₀₈ , and R ₃₀₆ and R ₃₀₇ , at least one combination is different from each other.)

(In the formula, R ₄₂ represents a linear alkyl group having 2 to 20 carbon atoms, and R ₄₇ represents a hydrogen atom or a methyl group.)
2. 1. The organic solvent is an organic solvent having an aromatic ring. Inkjet ink for forming an organic semiconductor thin film according to.
3. 3. In addition, it contains an insulating material. Or 2. Inkjet ink for forming an organic semiconductor thin film according to.
4. 3. The insulating material is a polymer material. Inkjet ink for forming an organic semiconductor thin film according to.
5.1. ~ 4. An organic semiconductor device including an organic semiconductor thin film obtained by using the inkjet ink for forming an organic semiconductor thin film according to any one of the above items.
6.1. ~ 4. A thin film transistor comprising an organic semiconductor thin film formed by using the inkjet ink for forming an organic semiconductor thin film according to any one of the above items.
7. 5. The organic semiconductor device described in 6. At least one type selected from the thin film transistors described in 5. The organic semiconductor device described in 6. An electronic device comprising the thin film transistor according to the above.

According to the present invention, it is possible to provide an inkjet ink for forming an organic semiconductor thin film, which exhibits excellent field effect mobility and further forms an organic thin film transistor having a small variation in field effect mobility.

It is sectional drawing of one aspect of the organic thin film transistor of this invention. It is sectional drawing of another aspect of the organic thin film transistor of this invention. It is a surface SEM image of an insulating film formed by a spin coating method. It is a surface SEM image of the insulating film formed by the reverse printing method. It is a surface SEM image of a source electrode or a drain electrode formed by a vacuum vapor deposition method. It is a surface SEM image of a source electrode or a drain electrode formed by the reverse printing method.

Hereinafter, the inkjet ink for forming an organic semiconductor thin film, an organic semiconductor element, a thin film transistor (organic transistor), and an electronic device of the present invention will be described in detail.
(Ink of the present invention)
The ink of the present invention is an inkjet ink for forming an organic semiconductor thin film, and is an organic semiconductor compound represented by the general formula (1-1), an organic semiconductor compound represented by the general formula (2-1), and a general formula (1). An organic semiconductor compound represented by 3-1), at least one organic semiconductor compound selected from the organic semiconductor compounds represented by the general formula (4-1), a boiling point of 180 ° C. or higher and 250 ° C. or lower, and a surface tension. It is an inkjet ink for forming an organic semiconductor thin film containing an organic solvent of 20 mN / m or more and 38 mN / m or less. The thin film transistor manufactured by using the ink of the present invention is characterized by exhibiting excellent field effect mobility and having a small variation in the field effect mobility. A notable feature of the inkjet ink for forming an organic semiconductor thin film of the present invention is that a homogeneous organic semiconductor thin film can be formed even when the surface of the base is rough. Generally, when an organic semiconductor film is formed on a base having a rough surface, the roughness of the base hinders the crystal growth of the organic semiconductor and impairs the homogeneity of the organic semiconductor thin film. Therefore, when an organic semiconductor thin film is formed on an electrode having a rough surface and an insulating film layer, a homogeneous organic semiconductor thin film cannot be obtained, which causes a decrease in field effect mobility and an increase in variation. However, when an organic semiconductor layer is formed by an inkjet method using the ink of the present invention, an electrode having a rough surface formed by a screen printing method, an inkjet method, a letterpress printing method, or the like and / or a screen printing method, an inkjet method, or a letterpress Even when a rough insulating film layer formed by a printing method or the like is used as an underlayer, a homogeneous organic semiconductor thin film can be formed, showing excellent field effect mobility, and further varying the field effect mobility. A small thin film transistor can be obtained (generally, it is formed by a printing method such as a screen printing method, an inkjet method, or a letterpress printing method, as compared with an electrode or an insulating film layer formed by a solid coating such as a vacuum deposition method or a spin coating method. The surface of the electrode and the insulating film layer is rough. Details will be described later.)

(Organic semiconductor compound used in the ink of the present invention)

The organic semiconductor compound represented by the general formula (1-1) will be described.

_{(Wherein, R 11} - and _{R 12} - is a group represented by any one of the following (II) or (I-II), at least one of a (II).
(I) is
A group of the general formula (1-2) or (1-3).

(Ar ₁₁ may have an aromatic hydrocarbon group or a hetero-aromatic _{group which may have a substituent, Ar 12} may have an aromatic hydrocarbon group or a substituent which may have a substituent. groups, R 1 _'is hydrogen atom, trialkylsilyl group having an alkyl group of 1 to 4 carbon atoms, having 1 to 20 carbon atoms alkyl group, an aromatic optionally having a substituent hydrocarbon group or a heteroaromatic It is a family group.)
(I-II)
Alkyl group having 2 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkyl group having 2 to 20 carbon atoms having a halogen atom, alkoxyalkyl group having 3 to 20 carbon atoms, alkylsulfanylalkyl having 3 to 20 carbon atoms Group, alkylaminoalkyl group with 3 to 20 carbon atoms, aromatic hydrocarbon group or heteroaromatic group, alkyl group with 1 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, carbon number having halogen atom An aromatic hydrocarbon group having an alkyl group of 1 to 20, an alkoxyalkyl group having 3 to 20 carbon atoms, an alkylsulfanyl alkyl group having 3 to 20 carbon atoms, or an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent or It is a group selected from complex aromatic groups. )
_{The organic semiconductor compound represented by the general formula (1-1) has a substituent R 11 on the} benzothioenobenzothiophene ([1] benzothiophene [3,2-b] [1] benzothiophene, hereinafter abbreviated as BTBT) skeleton. And R ₁₂ , where R ₁₁ and R ₁₂ are groups represented by either (I) or (I-II), but at least one is (I). It is a compound having the characteristics of.
(I) is
It is a group of the general formula (1-2) or (1-3) having a specific arylene acetylene structure, wherein (I-II) is an alkyl group having 2 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and the like. An alkyl group having 2 to 20 carbon atoms having a halogen atom, an alkoxyalkyl group having 3 to 20 carbon atoms, an alkylsulfanyl alkyl group having 3 to 20 carbon atoms, an alkylaminoalkyl group having 3 to 20 carbon atoms, and an aromatic hydrocarbon group. Alternatively, a heteroaromatic group, an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms as a substituent, and an alkyl having 2 to 20 carbon atoms having a halogen atom. Aromatic hydrocarbon group or heteroaromatic group having a group as a substituent, aromatic hydrocarbon group or heteroaromatic group having an alkoxyalkyl group having 3 to 20 carbon atoms as a substituent, alkylsulfanyl having 3 to 20 carbon atoms. It is a group selected from an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group as a substituent, and an aromatic hydrocarbon group or a heteroaromatic group having an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent. ..

_{Ar 11} of the substituent represented by the general formula (1-2) is particularly limited as long as it is an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent. However, for example, the following can be mentioned.

The aromatic hydrocarbon group which may have a substituent includes a phenyl group, a naphthyl group, an azulenyl group, an acenaphthenyl group, an anthranyl group, a phenanthryl group, a naphthacenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a peryleneyl group and a biphenyl group. An unsubstituted monocyclic or polycyclic aromatic hydrocarbon group having 6 to 24 carbon atoms such as a group, a p-terphenyl group and a quarter phenyl group.

o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, 2,6-xylyl group, mesityl group, juryl group, 4-ethylphenyl group, 4-n-propylphenyl group, 4 -Isopropylphenyl group, 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-decaphenyl group, 4-stearylphenyl group, 9,9'-dihexylfur An alkyl-substituted aromatic hydrocarbon group, a tolyl group, a 4-butenylphenyl group, a 4-octadecenylphenyl group in which the aromatic hydrocarbon group is substituted with an alkyl group having 1 to 18 carbon atoms, such as an olenyl group. An alkenyl-substituted aromatic hydrocarbon group in which the aromatic hydrocarbon group is substituted with an alkenyl group having 2 to 20 carbon atoms, such as.

The aromatic hydrocarbon groups such as 4-fluorophenyl group, 2,6-fluorophenyl group, 4-chlorophenyl group, 2,3,4,5,6-perfluorophenyl group are fluorine atom, chlorine atom and bromine. Halogenated aromatic hydrocarbon group substituted with halogen such as atom, 4- (2-ethoxyethyl) phenyl group, 4- (2-n-hexyloxyethyl) phenyl group, 4- (2-n-heptyloxy) Ethyl) phenyl group, 4- (2-n-tetradecyloxyethyl) phenyl group, 4- (2-cyclohexyloxyethyl) phenyl group, 4- (12-ethoxydodecyl) phenyl group, 4- (cyclohexyloxyethyl) An alkoxyalkyl-substituted aromatic hydrocarbon group in which the aromatic hydrocarbon group is substituted with an alkoxyalkyl group having 3 to 20 carbon atoms, such as a phenyl group.
4- (Methylsulfanylpropyl) phenyl group, 4- (2-n-hexylsulfanylethyl) phenyl group, 4- (3-n-decylsulfanylpropyl) phenyl group, 4- (cyclohexylsulfanylpropyl) phenyl group, etc. Alkyl sulphanyl alkyl-substituted aromatic hydrocarbon groups in which the aromatic hydrocarbon groups of the above are substituted with alkyl sul-phenyl alkyl groups having 3 to 20 carbon atoms.
Alkylamino having 3 to 20 carbon atoms as the aromatic hydrocarbon group, such as 4- (3-octylaminopropyl) phenyl group, 4- (3-dodecylaminopropyl) phenyl group, 4- (diethylaminoethyl) phenyl group, etc. Examples thereof include an alkylaminoalkyl-substituted aromatic hydrocarbon group substituted with an alkyl group, and the like.

Examples of the heteroaromatic group which may have a substituent include a pyrrolyl group, an indolyl group, a frill group, a thienyl group, an imidazolyl group, a benzofuryl group, a triazolyl group, a benzotriazolyl group, a benzothienyl group and a pyrazolyl group. , Indridinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, indolinyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, A 5- or 6-membered heteroaromatic group such as a thiadiazolyl group, a pyrorotiazolyl group, a pyrolopyridazinyl group, a tetrazolyl group, or an oxazolyl group, or a polycyclic heteroaromatic group obtained by condensing benzene with the heteroaromatic group. Group,
An alkyl-substituted heteroaromatic group in which the complex aromatic group is substituted with an alkyl group having 1 to 20 carbon atoms, such as a 5-methylthienyl group, a 5-hexylthienyl group, a 5-decatienyl group, and a 5-stearylthionyl group.

Halogenated heteroaromatic groups in which the above-mentioned heteroaromatic groups such as fluoropyridinyl group and fluoroindrill group are substituted with halogens such as fluorine atom, chlorine atom and bromine atom,
5- (2-ethoxyethyl) thienyl group, 5- (2-n-tetradecyloxyethyl) thienyl group, 5- (2-cyclohexyloxyethyl) thienyl group, 5- (12-ethoxydodecyl) thienyl group, etc. An alkoxyalkyl-substituted heteroaromatic group in which the aromatic hydrocarbon group is substituted with an alkoxyalkyl group having 3 to 20 carbon atoms.

5- (Methylsulfanylpropyl) thienyl group, 5- (2-n-hexylsulfanylethyl) thienyl group, 5- (3-n-decylsulfanylpropyl) thienyl group, 5- (cyclohexylsulfanylpropyl) thienyl group, etc. Alkyl sulfanyl alkyl substituted heteroaromatic group in which the aromatic hydrocarbon group of is substituted with an alkylsulfanylalkyl group having 3 to 20 carbon atoms,
Alkylaminoalkyl having 3 to 20 carbon atoms as the heteroaromatic group, such as 5- (3-octylaminopropyl) thienyl group, 5- (3-dodecylaminopropyl) thienyl group, 5- (diethylaminoethyl) thienyl group, etc. Examples include an alkylaminoalkyl-substituted heteroaromatic group substituted with a group, and the like.

_{Further, Ar 12} of the substituent represented by the general formula (1-3) is an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent. There are no particular restrictions, but the following can be mentioned, for example.

6 carbon atoms such as phenylene group, naphthylene group, azulenylene group, acenaphthenylene group, anthrylene group, phenanthrylene group, naphthacenylene group, fluorenylene group, pyrenylene group, chrysenylene group, peryleneylene group, biphenylene group, p-terphenylene group, quarterphenylene group, etc. ~ 24 monocyclic or polycyclic aromatic hydrocarbon groups,
The aromatic hydrocarbon group is an alkyl group having 1 to 10 carbon atoms, such as a trilene group, a xylylene group, an ethylphenylene group, a propylphenylene group, a butylphenylene group, a methylnaphthylene, or a 9,9'-dihexylfluorenylene group. Substituted alkyl-substituted aromatic hydrocarbon groups,

Examples thereof include halogenated aromatic hydrocarbon groups in which the aromatic hydrocarbon groups such as fluorophenylene group, chlorophenylene group and bromophenylne group are substituted with halogens such as fluorine atom, chlorine atom and bromine atom.
Furthermore, complex aromatic groups such as thienylene and pyridylene and complex aromatic groups in which these are substituted can also be used.

Moreover, the general formula R ₁ substituent represented by (1-3) _'is a hydrogen atom, trialkylsilyl group having an alkyl group of 1 to 4 carbon atoms, alkyl group having 1 to 20 carbon atoms, a substituent As long as it is an aromatic hydrocarbon group or a heteroaromatic group which may have, there is no particular limitation, and examples thereof include the following.

Examples of the trialkylsilyl group having an alkyl group having 1 to 4 carbon atoms include a trimethylsilyl group, a triethylsilyl group, a trin-propylsilyl group, a triisopropylsilyl group, a trin-butylsilyl group and a trisec-butyl group.
Examples of the alkyl group having 1 to 20 carbon atoms include 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 isopentyl group, a neopentyl group, an n-hexyl group, and 1 -Methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n-octyl group, tert-octyl Group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethyl Hexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n Linear, branched or cyclic alkyl groups such as −heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc.

The aromatic hydrocarbon group which may have a substituent includes a phenyl group, a naphthyl group, an azulenyl group, an acenaphthenyl group, an anthranyl group, a phenanthryl group, a naphthacenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a peryleneyl group and a biphenyl group. Monocyclic or polycyclic aromatic hydrocarbon groups having 6 to 24 carbon atoms, such as groups, p-terphenyl groups, quarterphenyl groups, etc.
o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, 2,6-xylyl group, mesityl group, juryl group, 4-ethylphenyl group, 4-n-propylphenyl group, 4 -Isopropylphenyl group, 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-decaphenyl group, 4-stearylphenyl group, 9,9'-dihexylfur An alkyl-substituted aromatic hydrocarbon group in which the aromatic hydrocarbon group is substituted with an alkyl group having 1 to 18 carbon atoms, such as an olenyl group.
An alkenyl-substituted aromatic hydrocarbon group in which the above-mentioned aromatic hydrocarbon group is substituted with an alkenyl group having 2 to 20 carbon atoms, such as a styryl group, a 4-butenylphenyl group, and a 4-octadecenylphenyl group.

The aromatic hydrocarbon groups such as 4-fluorophenyl group, 2,6-fluorophenyl group, 4-chlorophenyl group, 2,3,4,5,6-perfluorophenyl group are fluorine atom, chlorine atom and bromine. Halogenated aromatic hydrocarbon groups substituted with halogens such as atoms,
4- (2-ethoxyethyl) phenyl group, 4- (2-n-hexyloxyethyl) phenyl group, 4- (2-n-heptyloxyethyl) phenyl group, 4- (2-n-tetradecyloxyethyl) ) Phenyl group, 4- (2-cyclohexyloxyethyl) phenyl group, 4- (12-ethoxydodecyl) phenyl group, 4- (cyclohexyloxyethyl) phenyl group, etc. The aromatic hydrocarbon group has 3 to 20 carbon atoms. Alkoxyalkyl-substituted aromatic hydrocarbon groups substituted with alkoxyalkyl groups of

4- (Methylsulfanylpropyl) phenyl group, 4- (2-n-hexylsulfanylethyl) phenyl group, 4- (3-n-decylsulfanylpropyl) phenyl group, 4- (cyclohexylsulfanylpropyl) phenyl group, etc. Alkyl sulphanyl alkyl-substituted aromatic hydrocarbon groups in which the aromatic hydrocarbon groups of the above are substituted with alkyl sul-phenyl alkyl groups having 3 to 20 carbon atoms.
Alkylamino having 3 to 20 carbon atoms as the aromatic hydrocarbon group, such as 4- (3-octylaminopropyl) phenyl group, 4- (3-dodecylaminopropyl) phenyl group, 4- (diethylaminoethyl) phenyl group, etc. Examples thereof include an alkylaminoalkyl-substituted aromatic hydrocarbon group substituted with an alkyl group, and the like.

Examples of the heteroaromatic group which may have a substituent include a pyrrolyl group, an indolyl group, a frill group, a thienyl group, an imidazolyl group, a benzofuryl group, a triazolyl group, a benzotriazolyl group, a benzothienyl group and a pyrazolyl group. , Indridinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, indolinyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, A 5- or 6-membered heteroaromatic group such as a thiadiazolyl group, a pyrorotiazolyl group, a pyrolopyridazinyl group, a tetrazolyl group, or an oxazolyl group, or a polycyclic heteroaromatic group obtained by condensing benzene with the heteroaromatic group. An alkyl-substituted heteroaromatic group in which the heteroaromatic group is substituted with an alkyl group having 1 to 20 carbon atoms, such as a group, a 5-methylthienyl group, a 5-hexylthienyl group, a 5-decatienyl group, a 5-stearylthenyl group, etc.

5- (2-ethoxyethyl) thienyl, a halogenated heteroaromatic group in which the above heteroaromatic group is substituted with a halogen such as a fluorine atom, a chlorine atom or a bromine atom, such as a fluoropyridinyl group or a fluoroindryl group. The aromatic hydrocarbon group has a number of carbon atoms such as a group, a 5- (2-n-tetradecyloxyethyl) thienyl group, a 5- (2-cyclohexyloxyethyl) thienyl group, and a 5- (12-ethoxydodecyl) thienyl group. An alkoxyalkyl-substituted heteroaromatic group substituted with 3 to 20 alkoxyalkyl groups,

5- (Methylsulfanylpropyl) thienyl group, 5- (2-n-hexylsulfanylethyl) thienyl group, 5- (3-n-decylsulfanylpropyl) thienyl group, 5- (cyclohexylsulfanylpropyl) thienyl group, etc. Alkyl sulfanyl alkyl substituted heteroaromatic group in which the aromatic hydrocarbon group of is substituted with an alkylsulfanylalkyl group having 3 to 20 carbon atoms,
Alkylaminoalkyl having 3 to 20 carbon atoms as the heteroaromatic group, such as 5- (3-octylaminopropyl) thienyl group, 5- (3-dodecylaminopropyl) thienyl group, 5- (diethylaminoethyl) thienyl group, etc. Examples include an alkylaminoalkyl-substituted heteroaromatic group substituted with a group, and the like.

In addition, (I-II) is
Alkyl group having 2 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkyl group having 2 to 20 carbon atoms having a halogen atom, alkoxyalkyl group having 3 to 20 carbon atoms, alkylsulfanylalkyl having 3 to 20 carbon atoms An aromatic hydrocarbon having a group, an alkylaminoalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group or a heteroaromatic group, an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms as a substituent. Fragrance having a group or heteroaromatic group, an aromatic hydrocarbon group or heteroaromatic group having a halogen atom and an alkyl group having 2 to 20 carbon atoms as a substituent, and an alkoxyalkyl group having 3 to 20 carbon atoms as a substituent. Group hydrocarbon group or heteroaromatic group, aromatic hydrocarbon group or heteroaromatic group having an alkylsulfanylalkyl group having 3 to 20 carbon atoms as a substituent, alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent A group selected from an aromatic hydrocarbon group or a heteroaromatic group having
To exemplify (I-II),
The alkyl group having 2 to 20 carbon atoms includes an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, and 1-methylpentyl. Group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 1 -Methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group , N-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group and other linear, branched or cyclic alkyl groups,

Examples of the alkenyl group having 2 to 20 carbon atoms include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a decenyl group, a dodecenyl group, a tetradecenyl group, a hexadecenyl group, an octadecenyl group and a methylpentenyl group. , Cyclohexene, 4-methylcyclohexene and other linear, branched, cyclic alkenyl groups,
Examples of the alkyl group having a halogen atom and having 2 to 20 carbon atoms include a 2,2,3,3,3-pentafluoropropyl group, a 2,2,3,3,4,5,4-heptafluorobutyl group, and 2 , 2,3,3,4,5,5,5-nonafluoropentyl group, 2,2,3,3,4,5,5,6,6,6-undecafluorohexyl group, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyl group of the hydrogen atom of the alkyl group having 2 to 20 carbon atoms. Alkyl groups partially substituted with fluorine atoms,

Examples of the alkoxyalkyl group having 3 to 20 carbon atoms include 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group and 2-n. -Hexyloxyethyl group, 2- (2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 2 -N-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl group, 3-methoxypropyl group, 3-ethoxypropyl Group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3-n-butoxypropyl group, 3-n-pentyloxypropyl group, 3-n-hexyloxypropyl group, 3- (2'-ethyl) Butoxy) propyl group, 3-n-octyloxypropyl group, 3- (2'-ethylhexyloxy) propyl group, 3-n-decyloxypropyl group, 3-n-dodecyloxypropyl group, 3-n-tetradecyl Oxypropyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n- Hexyloxybutyl group, 4-n-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl Group, 5-n-pentyloxypentyl group, 6-methoxyhexyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n −Deciloxyhexyl group, 4-methoxycyclohexyl group, 7-methoxyheptyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, 8-ethoxyoctyl group, 9-methoxynonyl group, 9 -Ethoxynonyl group, 10-methoxydecyl group, 10-ethoxydecyl group, 10-n-butoxydecyl group, 11-methoxyundecyl group, 12-methoxydodecyl group, 12-ethoxydodecyl group, 12-isopropoxidedecyl group , 14-methoxytetradecyl group, cyclohexyloxyethyl group, cyclohexyloxypropyl group, etc. Branched or cyclic alkoxyalkyl groups,

Examples of the alkylsulfanylalkyl group having 3 to 20 carbon atoms include alkylsulfanylalkyl groups such as methylsulfanylpropyl group, ethylsulfanylpropyl group, butylsulfanylpropyl group and dodecylsulfanylpropyl group, 2-methylsulfanylethyl group and 2-ethylsulfanyl. Ethyl group, 2-n-propylsulfanyl ethyl group, 2-isopropylsulfanyl ethyl group, 2-n-butylsulfanyl ethyl group, 2-n-hexylsulfanyl ethyl group, 2- (2'-ethylbutylsulfanyl) ethyl group, 2-n-Heptylsulfanylethyl group, 2-n-octylsulfanylethyl group, 2- (2'-ethylhexylsulfanyl) ethyl group, 2-n-decylsulfanylethyl group, 2-n-dodecylsulfanylethyl group, 2- n-Tetradecylsulfanylethyl group, 2-cyclohexylsulfanylethyl group, 2-methylsulfanylpropyl group, 3-methylsulfanylpropyl group, 3-ethylsulfanylpropyl group, 3-n-propylsulfanylpropyl group, 3-isopropylsulfanylpropyl Group, 3-n-butyl sulfanyl propyl group, 3-n-pentyl sulfanyl propyl group, 3-n-hexyl sulfanyl propyl group, 3- (2'-ethylbutyl sulfanyl) propyl group, 3-n-octyl sulfanyl propyl group , 3- (2'-Ethylhexyl sulfanyl) propyl group, 3-n-decyl sulfanyl propyl group, 3-n-dodecyl sulfanyl propyl group, 3-n-tetradecyl sulfanyl propyl group, 3-cyclohexyl sulfanyl propyl group, 4- Methylsulfanylbutyl group, 4-ethylsulfanylbutyl group, 4-n-propylsulfanylbutyl group, 4-isopropylsulfanylbutyl group, 4-n-butylsulfanylbutyl group, 4-n-hexylsulfanylbutyl group, 4-n- Octylsulfanylbutyl group, 4-n-decylsulfanylbutyl group, 4-n-dodecylsulfanylbutyl group, 5-methylsulfanylpentyl group, 5-ethylsulfanylpentyl group, 5-n-propylsulfanylpentyl group, 5-n- Pentylsulfanyl Pentyl group, 6-methylsulfanylhexyl group, 6-ethylsulfanylhexyl group, 6-isopropylsulfanylhexyl group, 6-n-butylsulfanylhexyl group, 6-n-hexyl Sulfanylhexyl group, 6-n-decylsulfanylhexyl group, 4-methylsulfanylcyclohexyl group, 7-methylsulfanylheptyl group, 7-ethylsulfanylheptyl group, 7-isopropylsulfanylheptyl group, 8-methylsulfanyloctyl group, 8-- Ethylsulfanyloctyl group, 9-methylsulfanylnonyl group, 9-ethylsulfanylnonyl group, 10-methylsulfanyldecyl group, 10-ethylsulfanyldecyl group, 10-n-butylsulfanyldecyl group, 11-methylsulfanylundecyl group, Linear, branched or cyclic alkylsulfanylalkyls such as 12-methylsulfanyldodecyl group, 12-ethylsulfanyldodecyl group, 12-isopropylsulfanyldodecyl group, 14-methylsulfanyltetradecyl group, cyclohexylsulfanylethyl group, cyclohexylsulfanylpropyl group. Methyl group

In addition, 6-n-propylsulfanylhexyl group, 7-n-propylsulfanylheptyl group, 8-n-propylsulfanyloctyl group, 9-n-propylsulfanylnonyl group, 10-n-propylsulfanyldecyl group, 11-ethyl Sulfanyl undecyl group, 11-n-propyl sulfanyl undecyl group and the like can also be mentioned.

Examples of the alkylaminoalkyl group having 3 to 20 carbon atoms include N-methylaminoethyl group, N-ethylaminoethyl group, Nn-propylaminoethyl group, N-isopropylaminoethyl group and Nn-butylaminoethyl group. Group, Nn-hexylaminoethyl group, N-2-ethylbutylaminoethyl group, Nn-heptylaminoethyl group, Nn-octylaminoethyl group, N-2-ethylhexylaminoethyl group, N- n-decylaminoethyl group, Nn-dodecylaminoethyl group, Nn-tetradecylaminoethyl group, N-cyclohexylaminoethyl group, N-methylaminopropyl group, N-methylaminopropyl group, N-ethyl Aminopropyl group, Nn-propylaminopropyl group, N-isopropylaminopropyl group, Nn-butylaminopropyl group, Nn-pentylaminopropyl group, Nn-hexylaminopropyl group, N-2 -Ethylbutylaminopropyl group, Nn-octylaminopropyl group, N-2-ethylhexylaminopropyl group, Nn-decylaminopropyl group, Nn-dodecylaminopropyl group, Nn-tetradecylamino Propyl group, N-cyclohexylaminopropyl group, N-methylaminobutyl group, N-ethylaminobutyl group, Nn-propylaminobutyl group, N-isopropylaminobutyl group, Nn-butylaminobutyl group, N -N-hexylaminobutyl group, Nn-octylaminobutyl group, Nn-decylaminobutyl group, Nn-dodecylaminobutyl group, N-methylaminopentyl group, N-ethylaminopentyl group, N -N-propylaminopentyl group, Nn-pentylaminopentyl group, N-methylaminohexyl group, N-ethylaminohexyl group, N-isopropylaminohexyl group, Nn-butylaminohexyl group, Nn -Hexylaminohexyl group, Nn-decylaminohexyl group, N-methylaminocyclohexyl group, N-methylaminoheptyl group, N-ethylaminoheptyl group, N-isopropylaminoheptyl group, N-methylaminooctyl group, N-ethylaminooctyl group, N-methylaminononyl group, N-ethylaminononyl group, N-methylaminodecyl group, N-ethylaminodecyl group, Nn-butylaminodecyl group, N-methylaminoundecyl Group, N-methylaminododecyl group, N-ethylaminododecyl group, N-isopropi Linear, branched or cyclic N-alkylaminoalkyl groups such as ruaminododecyl group, N-methylaminotetradecyl group, N-cyclohexylaminoethyl group, N-cyclohexylaminopropyl group,

Examples of the aromatic hydrocarbon group or heteroaromatic group include a phenyl group, a naphthyl group, an azulenyl group, an acenaphthenyl group, an anthranyl group, a phenanthryl group, a naphthacenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a perylenel group, a biphenyl group and p. -Tarphenyl group, quarterphenyl group, pyrrolyl group, indolyl group, furyl group, thienyl group, imidazolyl group, benzofuryl group, triazolyl group, benzotriazolyl group, benzothienyl group, pyrazolyl group, indridinyl group, quinolinyl group, isoquinolinyl Group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, indolinyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridadinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, thiadiazolyl group, pyrolothiazolyl group, pyrolopyl A 2-fluorophenyl group in which the hydrogen atom of a dadynyl group, a tetrazolyl group, an oxazolyl group, etc., or these aromatic hydrocarbon groups or heteroaromatic groups is replaced with a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 3,5-difluorophenyl group, 2,3,4,5,6 − Halogen-substituted aromatic hydrocarbon groups such as pentafluorophenyl groups or heteroaromatic groups,

Examples of the aromatic hydrocarbon group or heteroaromatic group having an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms as a substituent include a 4-ethylphenyl group, a 4-n-propylphenyl group, and 4 -Isopropylphenyl group, 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-undecylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-octadecylphenyl group, 5-n-butyl-2-thienyl group, 5-n-hexyl-2-thienyl group, 5-n-octyl-2-thienyl group, 5-n-decyl-2-thienyl group, 5-n-tridecyl- An aromatic hydrocarbon group or heteroaromatic group in which the aromatic hydrocarbon group or heteroaromatic group has an alkyl group or alkenyl group having 2 to 20 carbon atoms as a substituent, such as a 2-thienyl group.

Examples of the aromatic hydrocarbon group or heteroaromatic group having an alkyl group having 2 to 20 carbon atoms having a halogen atom as a substituent include a 4-pentafluoropropylphenyl group, a 4-heptafluorobutylphenyl group and a 4-nonafluoro. The aromatic hydrocarbon group or heteroaromatic group, such as a pentylphenyl group, a 4-pentadecafluorooctylphenyl group, a 4-nonadecafluorodecylphenyl group, a 5-nonafluoropentyl-2-thienyl group, comprises the halogen atom. An aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 20 carbon atoms as a substituent,

Examples of the aromatic hydrocarbon group or heteroaromatic group having an alkoxyalkyl group having 3 to 20 carbon atoms as a substituent include a 4- (2-ethoxyethyl) phenyl group and a 4- (2-n-hexyloxyethyl) phenyl group. Group, 4- (2-n-octyloxyethyl) phenyl group, 4- (3-n-octyloxypropyl) phenyl group, 4- (3-n-tetradecyloxypropyl) phenyl group, 4- (4- (4-) n-octyloxybutyl) phenyl group, 4- (6-n-decyloxyhexyl) phenyl group, 4- (10-n-butoxydecyl) phenyl group, 5- (2-n-hexyloxyethyl) -2- An aromatic hydrocarbon group or heteroaromatic group in which the aromatic hydrocarbon group or heteroaromatic group has an alkoxyalkyl group having 3 to 20 carbon atoms as a substituent, such as a thienyl group.

Examples of the aromatic hydrocarbon group or heteroaromatic group having an alkylsulfanylalkyl group having 3 to 20 carbon atoms as a substituent include 4-methylsulfanylpropylphenyl group, 4-butylsulfanylpropylphenyl group and 4-dodecylsulfanylpropylphenyl. An aromatic hydrocarbon group or heteroaromatic group in which the aromatic hydrocarbon group or heteroaromatic group has an alkylsulfanylalkyl group having 3 to 20 carbon atoms as a substituent, such as a group, 5-methylsulfanylpropyl-2-thienyl group, etc. Group,
Examples of the aromatic hydrocarbon group or heteroaromatic group having an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent include an N-methylaminopropylphenyl group, an N-butylaminopropylphenyl group and an N-dodecylaminopropylphenyl group. An aromatic hydrocarbon group or heteroaromatic group in which the aromatic hydrocarbon group or heteroaromatic group has an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent, such as a group, N-methylaminopropyl-2-thienyl group, etc. Group, etc. can be mentioned.

Among the above (I-II), an alkyl group having 2 to 20 carbon atoms, an alkoxyalkyl group having 3 to 20 carbon atoms, an alkylsulfanyl alkyl group having 3 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms or carbon. An aromatic hydrocarbon group or a heteroaromatic group having an alkenyl group of several 2 to 20 as a substituent, an aromatic hydrocarbon group or a heteroaromatic group having an alkoxyalkyl group having 3 to 20 carbon atoms as a substituent, and a carbon number of carbons. An aromatic hydrocarbon group or a heteroaromatic group having 3 to 20 alkylsulfanylalkyl groups as substituents is preferable because it gives a high electric field effect mobility.
Further, in terms of suppressing variation in the mobility of the electric field effect, the above (I-II) is preferably an alkyl group having 2 to 20 carbon atoms, an alkoxyalkyl group having 3 to 20 carbon atoms, and an alkyl having 3 to 20 carbon atoms. It is a sulfanyl alkyl group, and particularly preferably an alkyl group having 4 to 18 carbon atoms, an alkoxyalkyl group having 4 to 18 carbon atoms, and an alkyl sulfanyl alkyl group having 4 to 18 carbon atoms.
Further, _{regarding R 11} and R ₁₂ , it is preferable that one of them is a group represented by (I) and the other is a group represented by (I-II).
Further, for R ₁₁ and R ₁₂ , one of them is a group represented by (I) and the other is a group represented by (I-II), and R ₁₁ is 2 of the BTBT skeleton. It is more preferred that it is attached to the position of the position and _{R 12} is attached to the position of the 7th position of the BTBT skeleton.

Specific organic semiconductor compounds used in the inkjet ink of the present invention having the substituents described above include, but are not limited to, the following.

Next, the organic semiconductor compound represented by the general formula (2-1) will be described.

(In the formula, R ₂₁ is any group of (II-I) and R ₂₂ is a group selected from any of (II-II).
(II-I)
A group of the general formula (2-2) or the general formula (2-3).

(Ar ₂₁ is an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 18 carbon atoms as a substituent, and the aromatic hydrocarbon group or the heteroaromatic group has a monocyclic or ring number. is a polycyclic 2 or 3 groups, Ar ₂₂ is an aromatic be substituted hydrocarbon group or an optionally substituted heteroaromatic group, R 2 _'is a hydrogen atom, the number of carbon atoms It is an aromatic hydrocarbon group or a heteroaromatic group which may have 1 to 20 alkyl groups and substituents.)
(II-II)
It is a group selected from a hydrogen atom, a methyl group, a cyano group, a fluoro group, and a trifluoromethyl group. )
The organic semiconductor compound represented by the general formula (2-1) is a compound having R ₂₁ and R ₂₂ as substituents in the BTBT skeleton, and at least one of the substituents has a general formula having a specific arylene acetylene structure. The group represented by (2-2) or (2-3), and the other substituent is a group selected from a hydrogen atom, a methyl group, a cyano group, a fluoro group, and a trifluoromethyl group. It has characteristics.

The organic semiconductor compound used in the inkjet ink of the present invention has improved solvent solubility by connecting the main skeleton containing the BTBT ring to an aromatic ring or the like via an acetylene moiety, and further expands the π-conjugated plane to produce an electric field effect. Mobility is improved.

Further, by shortening one of the substituents such as a hydrogen atom, a methyl group, a cyano group, a fluoro group, and a trifluoromethyl group, the interaction between the substituents is simplified and a homogeneous semiconductor film is provided. Is possible. That is, even with a simple wet method of "dropping ink droplets and drying the ink droplets", it is possible to provide an organic semiconductor film having high field effect mobility.

Next, the substituent of the organic semiconductor compound used in the inkjet ink of the present invention will be described.

_{The substituent R 22} of the compound represented by the general formula (2-1) of the present invention is a group selected from a hydrogen atom, a methyl group, a cyano group, a fluoro group and a trifluoromethyl group.

Meanwhile, the substituent _{R 21} of the compound represented by the general formula (2-1) of the present invention have the general formula (2-2) or (2-3)
It is a substituent represented by.

_{Ar 21} of the substituent represented by the general formula (2-2) is an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 18 carbon atoms as a substituent, and the aromatic hydrocarbon. As long as the group or the heteroaromatic group is a monocyclic group or a polycyclic group having 2 or 3 rings, the group is not particularly limited, and examples thereof include the following.

The aromatic hydrocarbon group of the aromatic hydrocarbon group having an alkyl group having 2 to 18 carbon atoms as a substituent includes a phenyl group, a naphthyl group, an azulenyl group, an acenaphthylenyl group, an acenaphthenyl group, an anthracenyl group, a phenanthryl group and a naphthacenyl group. , A monocyclic or polycyclic aromatic hydrocarbon group having 6 to 24 carbon atoms such as a fluorenyl group, a pyrenyl group, a chrysenyl group, a perylenel group, a biphenyl group, a p-terphenyl group and a quarterphenyl group.

_{Specific examples of the aromatic hydrocarbon group (Ar 21} ) having an alkyl group having 2 to 18 carbon atoms as a substituent include 4-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group and 4-. n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n- Examples include, but are not limited to, a decylphenyl group, a 9,9'-dihexylfluorenyl group, and the like.

The heteroaromatic group of the heteroaromatic group having an alkyl group having 2 to 18 carbon atoms as a substituent includes a pyrrolyl group, an indrill group, a frill group, a thienyl group, a bitienyl group, a turtieryl group, a quarterthenyl group and a thienotienyl group. Group, imidazolyl group, benzofuryl group, triazolyl group, benzotriazolyl group, benzothienyl group, pyrazolyl group, indridinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, indolinyl group, thiazolyl Group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, thiadiazolyl group, pyrorotiazolyl group, pyrrolopyridazinyl group, tetrazolyl group, oxazolyl group, bitienyl group, turtienyl group, quartertienyl group. Examples thereof include a 5-membered or 6-membered heteroaromatic group, a polycyclic heteroaromatic group obtained by condensing another aromatic group with the heteroaromatic group, and the like.

_{Specific examples of the heteroaromatic group (Ar 21} ) having an alkyl group having 2 to 18 carbon atoms as a substituent include 5-ethylthienyl group, 5-n-propylthienyl group, 5-isopropylthienyl group and 5-n. -Butylthenyl group, 5-n-pentylthenyl group, 5-n-hexylthenyl group, 5-n-heptylthenyl group, 5-n-octylthenyl group, 5-n-nonylthenyl group, 5-n-decylthenyl group , Etc. can be mentioned.

Among the above, Ar ₂₁ is preferably a phenyl group, a naphthyl group, a biphenyl group, a thienyl group, or a benzothienyl group having an alkyl group having 2 to 18 carbon atoms as a substituent from the viewpoint of solvent solubility, and has semiconductor characteristics (s). From the viewpoint of electric field effect mobility), an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 10 carbon atoms as a substituent is preferable, and therefore solvent solubility and semiconductor properties (electric field effect mobility). From both viewpoints, a phenyl group, a naphthyl group, a biphenyl group, a thienyl group, and a benzothienyl group having an alkyl group having 2 to 10 carbon atoms as a substituent are particularly preferable.

_{Ar 22} of the substituent represented by the general formula (2-3) is particularly limited as long as it is an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent. However, for example, the following can be mentioned.

Phenylene group, naphthylene group, azulenylene group, acenaphthenylene group, anthracenylene group, phenanthrenylene group, naphthacenylene group, fluorenylene group, pyrenylene group, chrysenylene group, peryleneylene group, biphenylene group, p-terphenylene group, quarterphenylene group, etc. Monocyclic or polycyclic aromatic hydrocarbon divalent groups with 6 to 24 carbon atoms,
Trilen group, xylylene group, ethylphenylene group, propylphenylene group, isopropylphenylene group, butylphenylene group, pentylphenylene group, hexylphenylene group, heptylphenylene group, octylphenylene group, nonylphenylene group, decylphenylene group, methylnaphthylene, An alkyl-substituted aromatic hydrocarbon divalent group in which the aromatic hydrocarbon divalent group is substituted with an alkyl group having 2 to 18 carbon atoms, such as a 9,9'-dihexylfluorenyl group.
Halogenated aromatic hydrocarbon divalent groups in which the above aromatic hydrocarbon divalent groups such as fluorophenylene group, chlorophenylene group and bromophenylne group are replaced with halogens such as fluorine atom, chlorine atom and bromine atom Can be mentioned.

Further, a complex aromatic divalent group such as thienylene and pyridylene and a complex aromatic divalent group in which these are substituted can also be used.

Further, denoted R _{2 'substituents} in the general formula (2-3) a hydrogen atom, an alkyl group, an aromatic hydrocarbon group optionally having substituent or a heteroaromatic group having 1 to 20 carbon atoms If so, there is no particular limitation, and examples thereof include the following.

Examples of the alkyl group having 1 to 20 carbon atoms include 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 isopentyl group, a neopentyl group, an n-hexyl group, and 1 -Methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n-octyl group, tert-octyl Group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethyl Hexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n Linear, branched or cyclic alkyl groups such as −heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc.

The aromatic hydrocarbon group which may have a substituent includes a phenyl group, a naphthyl group, an azulenyl group, an acenaphthenyl group, an anthranyl group, a phenanthryl group, a naphthacenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a peryleneyl group and a biphenyl group. A monocyclic or polycyclic aromatic hydrocarbon group having 6 to 24 carbon atoms such as a group, a p-terphenyl group and a quarter phenyl group.
o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, 2,6-xylyl group, mesityl group, juryl group, 4-ethylphenyl group, 4-n-propylphenyl group, 4 -Isopropylphenyl group, 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-decaphenyl group, 4-stearylphenyl group, 9,9'-dihexylfur An alkyl-substituted aromatic hydrocarbon group, a tolyl group, a 4-butenylphenyl group, a 4-octadecenylphenyl group in which the aromatic hydrocarbon group is substituted with an alkyl group having 1 to 18 carbon atoms, such as an olenyl group. Etc., an alkenyl-substituted aromatic hydrocarbon group in which the aromatic hydrocarbon group is substituted with an alkenyl group having 2 to 20 carbon atoms.

The aromatic hydrocarbon groups such as 4-fluorophenyl group, 2,6-fluorophenyl group, 4-chlorophenyl group, 2,3,4,5,6-perfluorophenyl group are fluorine atom, chlorine atom and bromine. Halogenated aromatic hydrocarbon groups substituted with halogens such as atoms,
4- (2-ethoxyethyl) phenyl group, 4- (2-n-hexyloxyethyl) phenyl group, 4- (2-n-heptyloxyethyl) phenyl group, 4- (2-n-tetradecyloxyethyl) ) Phenyl group, 4- (2-cyclohexyloxyethyl) phenyl group, 4- (12-ethoxydodecyl) phenyl group, 4- (cyclohexyloxyethyl) phenyl group, etc. The aromatic hydrocarbon group has 3 to 20 carbon atoms. Alkoxyalkyl-substituted aromatic hydrocarbon groups substituted with alkoxyalkyl groups of

4- (Methylsulfanylpropyl) phenyl group, 4- (2-n-hexylsulfanylethyl) phenyl group, 4- (3-n-decylsulfanylpropyl) phenyl group, 4- (cyclohexylsulfanylpropyl) phenyl group, etc. Alkyl sulphanyl alkyl-substituted aromatic hydrocarbon groups in which the aromatic hydrocarbon groups of the above are substituted with alkyl sul-phenyl alkyl groups having 3 to 20 carbon atoms.
Alkylamino having 3 to 20 carbon atoms as the aromatic hydrocarbon group, such as 4- (3-octylaminopropyl) phenyl group, 4- (3-dodecylaminopropyl) phenyl group, 4- (diethylaminoethyl) phenyl group, etc. Examples thereof include an alkylaminoalkyl-substituted aromatic hydrocarbon group substituted with an alkyl group, and the like.

Examples of the heteroaromatic group which may have a substituent include a pyrrolyl group, an indolyl group, a frill group, a thienyl group, an imidazolyl group, a benzofuryl group, a triazolyl group, a benzotriazolyl group, a benzothienyl group and a pyrazolyl group. , Indridinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, indolinyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, A 5-membered or 6-membered heteroaromatic group such as a thiadiazolyl group, a pyrorothiazolyl group, a pyrolopyridadinyl group, a tetrazolyl group, or an oxazolyl group, or a polycyclic heteroaromatic group in which benzene is condensed with the heteroaromatic group. Group,
An alkyl-substituted heteroaromatic group in which the complex aromatic group is substituted with an alkyl group having 1 to 20 carbon atoms, such as a 5-methylthienyl group, a 5-hexylthienyl group, a 5-decatienyl group, a 5-stearylthenyl group, etc.

Halogenated heteroaromatic groups in which the above-mentioned heteroaromatic groups such as fluoropyridinyl group and fluoroindrill group are substituted with halogens such as fluorine atom, chlorine atom and bromine atom,
5- (2-ethoxyethyl) thienyl group, 5- (2-n-tetradecyloxyethyl) thienyl group, 5- (2-cyclohexyloxyethyl) thienyl group, 5- (12-ethoxydodecyl) thienyl group, etc. An alkoxyalkyl-substituted heteroaromatic group in which the aromatic hydrocarbon group is substituted with an alkoxyalkyl group having 3 to 20 carbon atoms.

5- (Methylsulfanylpropyl) thienyl group, 5- (2-n-hexylsulfanylethyl) thienyl group, 5- (3-n-decylsulfanylpropyl) thienyl group, 5- (cyclohexylsulfanylpropyl) thienyl group, etc. Alkyl sulfanyl alkyl substituted heteroaromatic group in which the aromatic hydrocarbon group of is substituted with an alkylsulfanylalkyl group having 3 to 20 carbon atoms,
Alkylaminoalkyl having 3 to 20 carbon atoms as the heteroaromatic group, such as 5- (3-octylaminopropyl) thienyl group, 5- (3-dodecylaminopropyl) thienyl group, 5- (diethylaminoethyl) thienyl group, etc. Examples include an alkylaminoalkyl-substituted heteroaromatic group substituted with a group, and the like.

Specific examples of the organic semiconductor compound used in the inkjet ink of the present invention described above include, but are not limited to, the following.

Next, the organic semiconductor compound represented by the general formula (3-1) will be described.

(In the formula, R _{301 to} R ₃₁₂ are hydrogen atoms or arbitrary substituents, R ₃₀₁ and R ₃₁₂ are the same or different, R ₃₀₂ and R ₃₁₁ are the same or different, and R ₃₀₃ and R ₃₁₀ are the same. Or different, R ₃₀₄ and R ₃₀₉ are the same or different, R ₃₀₅ and R ₃₀₈ are the same or different, R ₃₀₆ and R ₃₀₇ are the same or different, but R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ and R ₃₀₃ and R. _{Of the six combinations of 310} , R ₃₀₄ and R ₃₀₉ , R ₃₀₅ and R ₃₀₈ , and R ₃₀₆ and R ₃₀₇ , at least one combination is different from each other.)

The organic semiconductor compound represented by the general formula (3-1) used in the ink of the present invention is a compound having _{R 301 to} R _{312 as a substituent on the dinaphthophene ring.}

The characteristic of the compound represented by the general formula (3-1) used in the inkjet ink of the present invention is that at least one of the six combinations related to the substituents is different. When the combinations of the above 6 sets are the same for each (that is, R ₃₀₁ and R ₃₁₂ are the same, R ₃₀₂ and R ₃₁₁ are the same, R ₃₀₃ and R ₃₁₀ are the same, R ₃₀₄ and R ₃₀₉ are the same, R _305. And R ₃₀₈ are the same, and R ₃₀₆ and R ₃₀₇ are the same), the symmetry of the molecule is C _2v , the symmetry is increased, and the crystallinity is enhanced. For this reason, the aggregating ability is excessively increased, the quality of the polycrystalline film produced by dropping the ink and drying the ink is deteriorated (generally, large crystal grains are precipitated and the homogeneity of the film is lowered), and the semiconductor characteristics (field effect mobility) are deteriorated. ) Decreases. On the other hand, since the organic semiconductor compound used in the inkjet ink of the present invention has low symmetry, the aggregating ability is appropriately controlled, and the quality of the polycrystalline film produced by dropping the ink and drying the ink is high, and therefore the semiconductor characteristics. (Field effect mobility) is high.

From this point of view, the positional structures of the substituents are R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ , R ₃₀₃ and R ₃₁₀ , R ₃₀₄ and R ₃₀₉ , R ₃₀₅ and R ₃₀₈ , R ₃₀₆ and R ₃₀₇ , It is preferable that at least one of the six combinations is different from each other, and the other combinations are the same as each other and are hydrogen atoms.

To obtain compounds with even higher field-effect mobility, R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ , R ₃₀₃ and R ₃₁₀ , R ₃₀₄ and R ₃₀₉ , R ₃₀₅ and R ₃₀₈ , R ₃₀₆ and R ₃₀₇ , Of the six combinations, R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ , R ₃₀₅ and R ₃₀₈ , and R ₃₀₆ and R ₃₀₇ are all the same hydrogen atom, and R ₃₀₃ and R ₃₁₀ are the same or Differently, R ₃₀₄ and R ₃₀₉ are the same or different, but it is particularly preferable that at least one of the two combinations of _{R 303} and R ₃₁₀ and R ₃₀₄ and R _{309 is different from each other.}

Next, the substituent of the organic semiconductor compound used in the inkjet ink of the present invention will be described.
_{The substituents R 301 to} R ₃₁₂ of the compound represented by the general formula (3-1) of the present invention can be used without limitation as long as they are known and commonly used as substituents for aromatic compounds. For example, acyclic groups can be used. as is not an oxygen atom, directly bonded each sulfur atom and nitrogen atom, -O - _- -CH 2 in the alkyl group (the alkyl group having 1 to 20 carbon atoms of formula or cyclic, - R ₃ ' _{C = CR 3 '-, -} CO -, - OCO -, - COO -, - S -, - SO 2 -, - SO -, - NH -, - NR 3' - or substituted with -C≡C- Te well, a hydrogen atom of the alkyl group, an aromatic group, a halogeno group may be substituted or by a nitrile group, (wherein, R 3 _'is an acyclic or cyclic alkyl having 1 to 20 carbon atoms (Representing a group.)), Harogeno group, aromatic group (the aromatic group is substituted with an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, a halogeno group, an aromatic group, or a nitrile group. _{-CH 2} − in the alkyl group _{may be −O−, −CR 3} ''= CR ₃ ''−, −CO so that oxygen atom, sulfur atom and nitrogen atom are not directly bonded to each other. -, - OCO -, - COO -, - S -, - SO 2 -, - SO -, - NH -, - NR 3 '' - or -C≡C- may be substituted with, in the alkyl group The hydrogen atom may be substituted with an aromatic group, a halogeno group, or a nitrile group (wherein R ₃ ″ represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms). Examples thereof include a group selected from a nitro group or a nitrile group (however, excluding the group represented by the general formula (3-2)).

R ₃₂₁ -C ≡ C- (R ₃₂₂ ) _p- (3-2)

(R ₃₂₁ represents an aromatic group which may have a substituent, R ₃₂₂ represents a phenylene group, and p represents an integer of 0 or 1.)

Specifically, -O so that the acyclic or cyclic alkyl group having 1 to 20 carbon atoms (-CH _2- in the alkyl group does not directly bond oxygen atom, sulfur atom and nitrogen atom, respectively). _{-, - R'C = CR 3 '} -, - CO -, - OCO -, - COO -, - S -, - SO 2 -, - SO -, - NH -, - NR 3' - or -C≡ may be substituted with C-, hydrogen atoms in the alkyl group, an aromatic group, a halogeno group or an optionally substituted by a nitrile group, (provided that the non-ring R 3 _'is 1 to 20 carbon atoms The formula or cyclic alkyl group is represented by (CA-1) a linear or branched alkyl group having 1 to 20 carbon atoms, (CA-2) an alicyclic alkyl group having 3 to 20 carbon atoms, (. CA-3) alkoxy group having 1 to 19 carbon atoms, (CA-4) alkoxyalkyl group having 2 to 19 carbon atoms, (CA-5) alkenyl group having 2 to 20 carbon atoms, (CA-6) Arcanoyl group with 2 to 20 carbon atoms, (CA-7) alkanoylalkyl group with 3 to 20 carbon atoms, (CA-8) alkoxycarbonyl group with 2 to 20 carbon atoms, (CA-9) number of carbon atoms 2 to 20 alkanoyloxy groups, (CA-10) alkylsulfanyl groups with 1 to 19 carbon atoms, (CA-11) alkylsulfanylalkyl groups with 2 to 19 carbon atoms, (CA-12) 1 carbon atoms ~ 19 Alkylsulfonyl groups, (CA-13) Alkylsulfonylalkyl groups with 2 to 19 carbon atoms, (CA-14) Alkylsulfinyl groups with 1 to 19 carbon atoms, (CA-15) Alkylsulfinyl groups with 2 to 19 carbon atoms 19 alkylsulfinyl alkyl groups, (CA-16) alkylamino groups with 1 to 19 carbon atoms, (CA-17) alkylaminoalkyl groups with 2 to 19 carbon atoms, (CA-18) 2 to 2 carbon atoms There are 20 alkynyl groups.

Among the above (CA-1) to (CA-18), from the viewpoint of improving the film-forming property and the electric field effect mobility of the organic semiconductor compound used in the inkjet ink of the present invention, the (CA-1) carbon atom Linear or branched alkyl group of number 1 to 20, (CA-2) alicyclic alkyl group of 3 to 20 carbon atoms, (CA-3) alkoxy group of number 1 to 19 carbon atoms, (CA-4) carbon Alkoxyalkyl group with 2 to 19 atoms, (CA-5) alkenyl group with 2 to 20 carbon atoms, (CA-10) alkylsulfanyl group with 1 to 19 carbon atoms, (CA-11) 2 carbon atoms Alkyl sulfanyl alkyl groups of ~ 19 or (CA-18) alkynyl groups having 2 to 20 carbon atoms are preferable.
In order to obtain a compound having a higher field effect mobility, (CA-1) a linear or branched alkyl group having 1 to 20 carbon atoms or (CA-4) an alkoxyalkyl group having 2 to 19 carbon atoms is used. Especially preferable.

Specific examples of (CA-1) include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and n-nonyl. Group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-eicosyl Linear alkyl groups such as groups,
Isopropyl group, isobutyl group, isopentyl group, neopentyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, 1-methylhexyl group, cyclohexylmethyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 3-ethylheptyl group, 2-propylpentyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5 , 5-Methylhexyl group, 1-methyldecyl group, 1-hexylheptyl group and other branched alkyl groups,
Cyclic alkyl groups such as cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc.
And so on.

Specific examples of (CA-4) include 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-n-. Hexyloxyethyl group, 2- (2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 2- n-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl group, 3-methoxypropyl group, 3-ethoxypropyl group , 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3-n-butoxypropyl group, 3-n-pentyloxypropyl group, 3-n-hexyloxypropyl group, 3- (2'-ethylbutoxy) ) Butyl group, 3-n-octyloxypropyl group, 3- (2'-ethylhexyloxy) propyl group, 3-n-decyloxypropyl group, 3-n-dodecyloxypropyl group, 3-n-tetradecyloxy Propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyl Oxybutyl group, 4-n-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group , 5-n-Pentyloxypentyl group, 6-methoxyhexyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n- Decyloxyhexyl group, 4-methoxycyclohexyl group, 7-methoxyheptyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, 8-ethoxyoctyl group, 9-methoxynonyl group, 9- Ethoxynonyl group, 10-methoxydecyl group, 10-ethoxydecyl group, 10-n-butoxydecyl group, 11-methoxyundecyl group, 12-methoxydodecyl group, 12-ethoxydodecyl group, 12-isopropoxidedecyl group, 14-methoxytetradecyl group, cyclohexyloxyethyl group, cyclohexyloxypropyl group,
And so on.

Specifically, the halogeno group is a fluoro group (fluorine atom), a chloro group (chlorine atom), a bromo group (bromine atom), and an iodo group (iodine atom).

Among the halogeno groups, a fluoro group and a chloro group are preferable, and a compound having a higher field effect mobility is preferable from the viewpoint of improving the film forming property and the field effect mobility of the organic semiconductor compound used in the inkjet ink of the present invention. In order to obtain, a fluoro group is particularly preferable.

Specifically, the aromatic group may be substituted with an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, a halogeno group, an aromatic group, or a nitrile group. _{-CH 2-} in the alkyl group _{is -O-, -CR 3} "= CR ₃ "-, -CO-, -OCO- so that oxygen atom, sulfur atom and nitrogen atom are not directly bonded to each other. _{, -COO -, - S -,} - SO 2 -, - SO -, - NH -, - NR 3 '' - or -C≡C- may be substituted with a hydrogen atom in the alkyl group, aromatic It may be substituted with a group group, a halogeno group, or a nitrile group (wherein R ₃ ″ represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms) is (CB-1. ) Unsubstituted aromatic hydrocarbon group or heteroaromatic group, (CB-2) halogenated aromatic hydrocarbon group or heteroaromatic group, (CB-3) aromatic hydrocarbon group or heteroaromatic group Aromatic hydrocarbon group or heteroaromatic group linked by bond, (CB-4) nitriled aromatic hydrocarbon group or heteroaromatic group, (CB-5) linear or branched alkyl having 1 to 20 carbon atoms Group-substituted aromatic hydrocarbon groups or heteroaromatic groups, (CB-6) alicyclic alkyl group-substituted aromatic hydrocarbon groups or heteroaromatic groups with 3 to 20 carbon atoms, (CB-7) carbon atoms Aromatic hydrocarbon group or heteroaromatic group substituted with an alkoxy group of number 1-19, (CB-8) Aromatic hydrocarbon group or heteroaromatic group substituted with an alkoxyalkyl group having 2 to 19 carbon atoms, (CB-8) -9) Aromatic hydrocarbon group or heteroaromatic group substituted with alkenyl group having 2 to 20 carbon atoms, (CB-10) Aromatic hydrocarbon group or heteroaromatic group substituted with alkanoyl group having 2 to 20 carbon atoms Group, (CB-11) alkanoylalkyl group substituted aromatic hydrocarbon group or heteroaromatic group with 3 to 20 carbon atoms, (CB-12) alkoxycarbonyl group substituted aromatic carbide with 2 to 20 carbon atoms Hydrogen group or heteroaromatic group, (CB-13) alkanoyloxy group substituted aromatic hydrocarbon group or heteroaromatic group with 2 to 20 carbon atoms, (CB-14) alkylsulfanyl having 1 to 19 carbon atoms Group-substituted aromatic hydrocarbon groups or heteroaromatic groups, (CB-15) alkylsulfanyl alkyl group-substituted aromatic hydrocarbon groups or heteroaromatic groups with 2 to 19 carbon atoms, (CB-16) carbon atoms Aromatic hydrocarbon groups or heteroaromatic groups with alkylsulfonyl group substitutions of numbers 1-19, (CB-17) An aromatic hydrocarbon group or a heteroaromatic group substituted with an alkylsulfonylalkyl group having 2 to 19 carbon atoms, and (CB-18) an aromatic hydrocarbon group substituted with an alkylsulfinyl group having 1 to 19 carbon atoms. Group or heteroaromatic group, (CB-19) alkylsulfinyl alkyl group substituted aromatic hydrocarbon group or heteroaromatic group with 2 to 19 carbon atoms, (CB-20) alkylamino with 1 to 19 carbon atoms Group-substituted aromatic hydrocarbon group or heteroaromatic group, (CB-21) Alkylaminoalkyl group with 2 to 19 carbon atoms Substituted aromatic hydrocarbon group or heteroaromatic group, (CB-22) Carbon atom It is an aromatic hydrocarbon group or a heteroaromatic group substituted with an alkynyl group of several numbers 2 to 20.

Among the above (CB-1) to (CB-22), (CB-1) is not substituted from the viewpoint of improving the film-forming property and the electric field effect mobility of the organic semiconductor compound used in the inkjet ink of the present invention. Aromatic hydrocarbon group or heteroaromatic group, (CB-2) halogenated aromatic hydrocarbon group or heteroaromatic group, (CB-3) aromatic hydrocarbon group or heteroaromatic group are linked by a single bond. (CB-5) Aromatic hydrocarbon group or heteroaromatic group substituted with a linear or branched alkyl group having 1 to 20 carbon atoms, (CB-6) number of carbon atoms. An aromatic hydrocarbon group or a heteroaromatic group substituted with an alicyclic alkyl group of 1 to 20, (CB-7) an aromatic hydrocarbon group or a heteroaromatic group substituted with an alkoxy group having 1 to 19 carbon atoms, (CB-7). CB-8) Aromatic hydrocarbon group or heteroaromatic group substituted with an alkoxyalkyl group having 2 to 19 carbon atoms, (CB-9) Aromatic hydrocarbon group or complex substituted with an alkenyl group having 2 to 20 carbon atoms Aromatic group, (CB-14) Aromatic hydrocarbon group or heteroaromatic group substituted with alkyl sulfanyl group having 1 to 19 carbon atoms, (CB-15) Alkyl sulphanyl alkyl group substituted with 2 to 19 carbon atoms Aromatic hydrocarbon group or heteroaromatic group, (CB-20) Aromatic hydrocarbon group or heteroaromatic group substituted with an alkylamino group having 1 to 19 carbon atoms, (CB-21) 2 to 19 carbon atoms An aromatic hydrocarbon group or a heteroaromatic group substituted with an alkylaminoalkyl group is preferable, and an aromatic hydrocarbon group or a heteroaromatic group substituted with an alkynyl group having (CB-22) 2 to 20 carbon atoms is preferable.
In order to obtain a compound having a higher electric field effect mobility, (CB-1) an unsubstituted aromatic hydrocarbon group or a heteroaromatic group, and (CB-2) a halogenated aromatic hydrocarbon group or a heteroaromatic group , (CB-3) Aromatic hydrocarbon group or heteroaromatic group in which aromatic hydrocarbon groups or heteroaromatic groups are linked by a single bond, (CB-5) Linear or branched alkyl having 1 to 20 carbon atoms. Aromatic hydrocarbon group or heteroaromatic group substituted with a group, (CB-6) aromatic hydrocarbon group or heteroaromatic group substituted with an alicyclic alkyl group having 1 to 20 carbon atoms, (CB-7) carbon atom Aromatic hydrocarbon groups or heteroaromatic groups substituted with an alkoxy group of numbers 1 to 19 and (CB-8) aromatic hydrocarbon groups or heteroaromatic groups substituted with an alkoxyalkyl group having 2 to 19 carbon atoms are particularly preferable. ..

Specific examples of (CB-1) include an unsubstituted carbon number such as a phenyl group, a naphthyl group, an azulenyl group, an acenaphthenyl group, an anthranyl group, a phenanthryl group, a naphthacenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group and a perylenel group. 6 to 24 monocyclic or polycyclic aromatic hydrocarbon groups,
Pyrrolyl group, indrill group, frill group, thienyl group, imidazolyl group, benzofuryl group, triazolyl group, benzotriazolyl group, benzothienyl group, pyrazolyl group, indridinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, dibenzofuranyl group , Dibenzothiophenyl group, indolinyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, thiadiazinyl group, oxadiazolyl group, benzoquinolinyl group, thiadiazolyl group, pyrorotiazolyl group, pyrrolopyridazinyl group, tetrazolyl group,

An unsubstituted 5- or 6-membered heteroaromatic group such as an oxazolyl group, or a polycyclic heteroaromatic group in which another aromatic group is condensed with the heteroaromatic group.
And so on.

Specific examples of (CB-2) include 4-fluorophenyl group, 2,6-fluorophenyl group, 4-chlorophenyl group, 2,3,4,5,6-perfluorophenyl group and fluoropyridinyl group. , Fluoroindrill group and the like, wherein the aromatic hydrocarbon group or heteroaromatic group is substituted with a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group.

Specific examples of (CB-3) include a biphenyl group, a terphenyl group, a binaphthyl group, a bipyridyl group, a bitienyl group, a terthienyl group, a quaterthienyl group, a quinctyenyl group, a sexithienyl group, a frillphenyl group, a thienylphenyl group and the like. Can be done.

Specific examples of (CB-5) include tolyl group, xsilyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group, n-butylphenyl group, tert. -Butylphenyl group, n-pentylphenyl group, n-hexylphenyl group, n-heptylphenyl group, n-octylphenyl group, 2-ethylhexylphenyl group, n-decaphenyl group, stearylphenyl group, 5-methylthienyl group , 5-Hexylthienyl group, 5-decatienyl group, 5-stearylthenyl group and the like.

Specific examples of (CB-6) include a cyclohexylphenyl group, a 4-methylcyclohexylphenyl group, a 4-ethylcyclohexylphenyl group and the like.
Specific examples of (CB-7) include methoxyphenyl group, ethoxyphenyl group, propoxyphenyl group, isopropoxyphenyl group, butoxyphenyl group, pentyloxyphenyl group, hexyloxyphenyl group, heptyloxyphenyl group, and octyloxyphenyl. Examples thereof include a group, a 2-ethylhexyloxyphenyl group, a decyloxyphenyl group, a dodecyloxyphenyl group, a stearyloxyphenyl group and the like.

Specific examples of (CB-8) include 4- (2-ethoxyethyl) phenyl group, 4- (2-n-hexyloxyethyl) phenyl group, 4- (2-n-heptyloxyethyl) phenyl group, 4- (2-n-Tetradecyloxyethyl) phenyl group, 4- (2-cyclohexyloxyethyl) phenyl group, 4- (12-ethoxydodecyl) phenyl group, 4- (cyclohexyloxyethyl) phenyl group, 5- (2-ethoxyethyl) thienyl group, 5- (2-n-tetradecyloxyethyl) thienyl group, 5- (2-cyclohexyloxyethyl) thienyl group, 5- (12-ethoxydodecyl) thienyl group and the like. Can be done.

Specific examples of the organic semiconductor compound used in the inkjet ink of the present invention are shown below, but the compound used in the present invention is not limited thereto.

Next, the organic semiconductor compound represented by the general formula (4-1) will be described.

（式中、Ｒ_４２は炭素原子数２〜２０の直鎖アルキル基を表し、Ｒ_４７は、水素原子またはメチル基を表す。）

(In the formula, R ₄₂ represents a linear alkyl group having 2 to 20 carbon atoms, and R ₄₇ represents a hydrogen atom or a methyl group.)

The organic semiconductor compound represented by the general formula (4-1) is a compound having R ₄₂ and R ₄₇ as substituents on the dithienobenzodithiophene ring.

The characteristic of the compound represented by the general formula (4-1) used in the inkjet ink of the present invention is that substituents having different alkyl chain lengths are introduced into the substituents _{R 42} and R _47. .. When R ₄₂ and R ₄₇ are the same substituent, the symmetry of the molecule _{becomes C 2h} , so that the symmetry becomes high and the crystallinity becomes excessively high. For this reason, the aggregating ability is excessively increased, and the film quality of the polycrystalline film produced by dropping the ink and drying the ink is deteriorated (generally, large crystal grains are precipitated and the uniformity of the film is lowered), and the film is manufactured by such a method. The semiconductor characteristics (electricity effect mobility) of the formed film are reduced. On the other hand, since the organic semiconductor compound used in the inkjet ink of the present invention has low symmetry, the aggregating ability is appropriately controlled, and the quality of the polycrystalline film produced by dropping the ink and drying the ink is high. Even a film manufactured by such a method exhibits high semiconductor characteristics (field effect mobility).

From the viewpoint of solvent solubility, R ₄₂ is preferably a linear alkyl group having 2 to 12 carbon atoms.

Specific examples of the organic semiconductor compound used in the inkjet ink of the present invention will be shown below, but the organic semiconductor compound used in the present invention is not limited thereto.

(Organic solvent used in the ink of the present invention)
As the organic solvent used in the inkjet ink for forming an organic semiconductor thin film used in the present invention, an organic solvent having a boiling point of 180 ° C. or higher and 250 ° C. or lower and a surface tension of 20 mN / m or higher and 38 mN / m or lower is selected.
Specifically, aliphatic solvents such as n-undecane, n-dodecane, n-tridecane, 1-undecene, 1-dodecene, and 1-tridecene,
n-butylbenzene, n-pentylbenzene, isopentylbenzene, neopentylbenzene, n-hexylbenzene, 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 1,3,5-triethylbenzene, Aromatic solvents such as tetraline, inden, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, benzyl acetate, benzyl bromide, 2-bromotoluene, etc.
Complex aromatic solvents such as quinoline, 2-butylthiophene, 3-butylthiophene, 2-pentylthiophene,
Ether-based solvents such as propoxybenzene, butoxybenzene, pentyloxybenzene, hexyloxybenzene, and allylphenyl ether,
Ketone solvents such as 5-nonanonone, 2-decanone, 3-decanone, isophorone, propiophenone, butyrophenone, valerophenone, isovalerophenone, phenylacetone, benzylacetone, benzylethylketone, etc.
Etc., but are not limited to these.
Among them, a solvent having an aromatic ring is particularly preferable from the viewpoint of solubility. Specifically, n-butylbenzene, n-pentylbenzene, isopentylbenzene, neopentylbenzene, n-hexylbenzene, 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 1,3. 5-Triethylbenzene, tetraline, inden, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, benzyl acetate, benzyl bromide, 2-bromotoluene, propoxybenzene, butoxybenzene, pentyloxybenzene, hexyloxybenzene , Allylphenyl ether, propiophenone, butyrophenone, valerophenone, isovalerophenone, phenylacetone, benzylacetone, benzylethylketone and the like are preferable.
The lower limit of the surface tension of the solvent depends on the inkjet head used. In general, it is known that when the surface tension of ink becomes low, it cannot be ejected by the inkjet method. For example, Ricoh's RICOH MH series may be 28 mN / m, and Microjet's GlassJet series may be used. For example, it is 20 mN / m.

The inkjet ink of the present invention is prepared by dissolving any of the organic semiconductor compounds in an organic solvent having a boiling point of 180 ° C. or higher and 250 ° C. or lower and a surface tension of 20 mN / m or higher and 38 mN / m or lower.

The concentration of the organic semiconductor compound of the present invention in the prepared liquid composition is preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and further 0.1 to 0.1% by weight. More preferably, it is 2% by weight.
Further, two or more kinds of organic solvents may be mixed and used.
(Other components used in the ink of the present invention)
The organic semiconductor ink of the present invention is not limited to the organic semiconductor compound used in the inkjet ink of the present invention, depending on the application, other organic semiconductor materials, that is, electron donating materials, electron accepting materials, electron transporting materials, and the like. It may include a hole transporting material, a light emitting material, a light absorbing material and the like. Examples of such a material include a π-conjugated polymer or oligomer exhibiting semiconducting properties, a non-π-conjugated polymer or oligomer exhibiting semiconducting properties, and a low-molecular-weight organic semiconductor compound.
Further, the inkjet ink of the present invention may contain an insulating material or the like in addition to the above-mentioned organic semiconductor compound and solvent, depending on the intended use. As described above, the thin film transistor manufactured by using the ink of the present invention can form a homogeneous organic semiconductor thin film even when a rough electrode and an insulating film layer are used, and exhibits excellent field effect mobility. Further, it is possible to obtain a thin film transistor having a small variation in field effect mobility. The addition of an insulating material is preferred in terms of this effect.

Examples of the above-mentioned insulating material include thermoplastic resins such as polystyrene, polymethyl methacrylate (PMMA), acrylic resin and polyester resin, epoxy resins, urethane resins, phenol resins, unsaturated polyester resins, alkyd resins and melamine resins. Thermosetting resins such as, UV curable resins, other polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, etc. Examples thereof include polymer materials such as thermoplastic (PC), cellulose triacetate (TAC), and cellulose acetate propionate (CAP). Among them, thermoplastic resins such as polystyrene, polymethylmethacrylate (PMMA), acrylic resin and polyester resin are particularly preferable.

(Organic semiconductor element)
Examples of the organic semiconductor device of the present invention include a diode, a thin film transistor, a photodiode, a light emitting diode, a light emitting transistor, a photoelectric conversion element, and a thin film solar cell.
Among them, the organic semiconductor thin film formed by using the organic semiconductor ink used in the present invention has a high field effect mobility and can suppress the variation in the field effect mobility to a small value, so that it is a thin film transistor or a light emitting device. The application to is particularly useful.

(Thin film transistor)
Next, the thin film transistor of the present invention will be described.
The thin film transistor usually has a source electrode, a drain electrode and a gate electrode, a gate insulating film layer, and an organic semiconductor thin film, and there are various types of transistors depending on the arrangement of each electrode and each layer. The organic semiconductor material is not limited to the type of transistor, and can be used for any transistor. For the types of transistors, refer to Aldrich's Materials Science Basics No. 6, "Basics of Organic Transistors".

Explaining the bottom contact type shown in FIG. 1 in detail as an example, 1 is a substrate, 2 is a gate electrode, 3 is a gate insulating film layer, 4 is a source electrode, 5 is a drain electrode, and 6 is an organic semiconductor.

The substrate is made of glass or a flexible resin sheet, and for example, a plastic film can be used as the sheet. Examples of the plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate (PC). , A film composed of cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like. As described above, by using the plastic film, the weight can be reduced as compared with the case of using the glass substrate, the portability can be improved, and the resistance to impact can be improved.

The electrode material of the gate electrode, source electrode, or drain electrode is not particularly limited as long as it is a conductive material, and platinum, gold, silver, nickel, chromium, copper, iron, tin, tin oxide / antimony, indium tin oxide / tin oxide. (ITO), fluorine-doped zinc oxide, carbon, graphite, glassy carbon, silver paste and carbon paste, lithium, beryllium, sodium, magnesium, potassium, calcium, scandium, titanium, manganese, zirconium, gallium, niobium, sodium, sodium- Metal electrodes such as potassium alloy, magnesium, lithium, aluminum, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide mixture, lithium / aluminum mixture, etc. are used, but doping etc. Known conductive polymers having improved conductivity, for example, conductive polyaniline, conductive polypyrrole, conductive polythiophene, and a complex of polyethylenedioxythiophene and polystyrene sulfonic acid are also preferably used.

As a method for forming the electrode, a method of forming an electrode by using a known photolithography method or a lift-off method of a conductive thin film formed by using a method such as vapor deposition or sputtering from the above as a raw material, or a metal foil such as aluminum or copper. There is a method of etching using a resist such as thermal transfer or inkjet on the top. Further, the conductive polymer solution, the dispersion liquid, or the conductive fine particle dispersion liquid may be directly patterned by inkjet, or may be formed from the coating film by lithograph, laser ablation, or the like. Further, a method of patterning an ink containing a conductive polymer or conductive fine particles, a conductive paste, or the like by a printing method such as a letterpress printing method, an intaglio printing method, a lithographic printing method, a reverse printing method, or a screen printing method can also be used.

The gate insulating film layer is a thermoplastic resin such as parylene, polystyrene, acrylic resin or polyester resin, a thermosetting resin such as epoxy resin, urethane resin, phenol resin, unsaturated polyester resin, alkyd resin or melamine resin, or UV curable. An organic thin film such as a resin can be preferably used, but an inorganic material such as a silicon oxide film can also be used.

The gate insulating film layer is a spin coating method, casting method, dip method, inkjet method, doctor blade method, screen printing method, offset printing method, letterpress printing method, reverse printing method, micro contact printing method, wire bar coating method, spray coating. A thin film can be produced by a known wet film forming method such as a method or a dispensing method, and may be patterned into a shape required by a photolithography method if necessary.

The organic semiconductor thin film is formed by ejecting the organic semiconductor ink of the present invention onto a printed matter (on a printed object, a source electrode and a drain electrode, and between them, an insulating film layer, etc.) by an inkjet method, and drying the landed ink. Can be formed.

The thin film transistor manufactured by using the ink of the present invention is characterized by exhibiting excellent field effect mobility and having a small variation in the field effect mobility. A notable feature of the inkjet ink for forming an organic semiconductor thin film of the present invention is that a homogeneous organic semiconductor thin film can be formed even when the surface of the base is rough. Generally, when an organic semiconductor film is formed on a base having a rough surface, the roughness of the base hinders the crystal growth of the organic semiconductor and impairs the homogeneity of the organic semiconductor thin film. Therefore, when an organic semiconductor thin film is formed on an electrode having a rough surface and an insulating film layer, a homogeneous organic semiconductor thin film cannot be obtained, which causes a decrease in field effect mobility and an increase in variation. However, when the ink of the present invention is used, the surface-rough electrode formed by the screen printing method, the inkjet method, the letterpress printing method, etc. and the surface-rough insulation formed by the screen printing method, the inkjet method, the letterpress printing method, etc. Even when a film layer is used, a homogeneous organic semiconductor thin film can be formed, and a thin film transistor having high field effect mobility and small variation in characteristics can be obtained.

Further, the organic semiconductor thin film may be annealed after the film formation, if necessary, for the purpose of improving the crystallinity, improving the semiconductor characteristics (field effect mobility), and removing the residual solvent. .. The annealing time and temperature can be appropriately selected depending on the organic semiconductor compound used.

Further, as shown in FIG. 2, a partition wall layer may be formed so as to surround the source electrode and the drain electrode. Taking the bottom contact type as an example, 1 is a substrate, 2 is a gate electrode, 3 is a gate insulating film layer, 4 is a source electrode, 5 is a drain electrode, 6 is an organic semiconductor, and 7 is a partition wall layer. By providing a partition layer after forming the source electrode and drain electrode and selectively dropping the organic semiconductor ink only on the portion surrounded by the partition layer, the film thickness of the organic semiconductor thin film can be controlled, and the field effect mobility can be controlled. The variation can be further suppressed.

The thin film transistor of the present invention can be suitably used as a switching transistor for pixels constituting a display, a signal driver circuit element, a memory circuit element, a signal processing circuit element, and the like. Examples of displays include liquid crystal displays, distributed liquid crystal displays, electrophoretic displays, particle rotating display elements, electrochromic displays, organic electroluminescence displays, electronic paper and the like.

(Electronic device)
The electronic device of the present invention is an electronic device using the organic semiconductor element, for example, sensors such as a diode, a gas sensor, a biosensor, a blood sensor, an immunosensor, an artificial retina, and a taste sensor, a logic circuit, and the like. RFID and the like can be mentioned.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

(Example 1)
<Manufacturing of compound E-1>
Compound E-1 was produced according to the method described in Example 19 of WO2014-038708.

<Manufacturing of ink E-1>
Compound E-1 was dissolved in butoxybenzene (boiling point 210 ° C., surface tension 30.4 mN / m) so as to have a concentration of 0.4 wt% to produce ink E-1.
The surface tension of the solvent is the automatic surface tension meter CBVP-A3 type instruction manual using an automatic surface tension meter CBVP-A3 type (manufactured by Kyowa Interface Science Co., Ltd.) in the atmosphere of room temperature 23 ° C. and humidity 50%. VOL No. The measurement was performed according to the method described in the section "11. Measurement" of 90.
<Manufacturing of thin film transistor E-1>
A test element of a thin film transistor having a BGBC (bottom gate bottom contact) type structure was manufactured by the following procedure.
First, an electrode having a thickness of 90 nm was formed as a gate electrode on a non-alkali glass having a thickness of 0.7 mm by a sputtering method using chromium.
Next, as the gate insulating film layer, the resin ink produced according to the method of Comparative Example 2 of Publication No. 2010-265423 was spin-coated on the support on which the gate electrode was formed to form an insulating film layer having a thickness of about 700 nm. .. The surface roughness Ra of the insulating film layer formed by the spin coating method was less than 1 nm. The surface roughness Ra was measured using VertScan 4.0 manufactured by Ryoka System Co., Ltd. Further, the surface SEM of the insulating film layer formed by the spin coating method.
The image is shown in FIG. The foreign matter in the center of the image is very smooth and difficult to measure by SEM.
The particles were intentionally mixed for the purpose of focusing in order to enable SEM measurement of the insulating film surface, and the surface roughness Ra was measured in a portion free of foreign matter.

Next, gold was vacuum-deposited on the previously formed insulating film layer as a source electrode and a drain electrode to form a gold electrode having a thickness of 30 nm. The surface roughness Ra of the electrode formed by the vacuum vapor deposition method was less than 1 nm. Further, a surface SEM image of the electrode formed by the vacuum vapor deposition method is shown in FIG. The channel length between the source electrode and the drain electrode was 25 μm.
Next, a fluororesin was used as the partition wall layer, and a rectangular partition wall layer was formed by an inkjet method so as to surround the channel region between the source electrode and the drain electrode described above.
Next, as an organic semiconductor thin film, ink E-1 is dropped onto the channel portion between the source electrode and the drain electrode formed earlier by an inkjet method, and after the film is formed, an element is used using a hot plate (to remove the solvent). Was heat-treated at 80 ° C. for 10 minutes to form an organic semiconductor thin film.
In this way, the thin film transistor E-1 was manufactured.
<Evaluation of thin film transistor E-1>
The semiconductor characteristics (field effect mobility) of the thin film transistor thus obtained were evaluated. The semiconductor characteristics (field effect mobility) are 20 to -30V, voltage on the gate electrode using a semiconductor parameter measuring device (S4200, manufactured by Caseley) with the source electrode grounded and -30V applied to the drain electrode. While applying a sweep of (Vg), the current (Id) flowing through the drain electrode was measured, and it was obtained from the inclination of √Id−Vg using (Equation 1). The unit is cm ² / V · s.
_{I d = (W / 2L)} · C · μ · (V g -V T) 2 ( Equation 1)

The evaluation was performed based on the values of the field effect mobility and the coefficient of variation CV.
For the field effect mobility, the value of the field effect mobility obtained in the above measurement was arithmetically averaged for 10 transistors. The field-effect mobility of the transistor was evaluated on a scale of 1 to 5 based on the following criteria.
5: 1.0 ^cm 2 / Vs or more 4: 0.5 ^cm 2 / Vs or more, 1.0 ^cm 2 / Vs less than 3: 0.1 ^cm 2 / Vs or more, 0.5 cm ² / Vs less than 2: 0 .01 cm ² / Vs or more, 0.1 ^cm 2 / Vs less than 1: less than 0.01 ^cm 2 / Vs, or non-evaluable

The coefficient of variation CV, which is an index of variation, is a value obtained by multiplying the arithmetic mean of the field effect mobility values obtained in the above measurement by the standard deviation for 10 transistors and displaying it as%. .. The standard deviation of the transistor was evaluated on a scale of 1 to 5 based on the following criteria.
5: CV is less than 25% 4: CV is 25% or more and less than 30% 3: CV is 30% or more and less than 40% 2: CV is 40% or more and less than 50% 1: CV is 50% or more Describe.

(Example 2)

<Manufacturing of compound E-2>
Compound E-2 was produced according to the method described in Example 10 of WO2014-038708.

<Manufacturing of ink E-2>
Ink E-2 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-2.
<Manufacturing of thin film transistor E-2>
The thin film transistor E-2 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-2.
<Evaluation of thin film transistor E-2>
The thin film transistor E-2 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-2.
The evaluation results are shown in Table 1.

(Example 3)
<Manufacturing of compound E-3>
Compound E-3 was produced according to the method described in Example 2 of WO2014-0370808.

<Manufacturing of ink E-3>
Ink E-3 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-3.
<Manufacturing of thin film transistor E-3>
The thin film transistor E-3 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-3.
<Evaluation of thin film transistor E-3>
The thin film transistor E-3 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-3.
The evaluation results are shown in Table 1.

(Example 4)
<Manufacturing of compound E-4>
Compound E-4 was produced according to the method described in Example 11 of WO2014-038708.

<Manufacturing of ink E-4>
Ink E-4 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-4.
<Manufacturing of thin film transistor E-4>
The thin film transistor E-4 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-4.
<Evaluation of thin film transistor E-4>
The thin film transistor E-4 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-4.
The evaluation results are shown in Table 1.

(Example 5)
<Manufacturing of Compound E-5>
Compound E-5 was produced according to the method described in Example 18 of WO2014-038708.

<Manufacturing of ink E-5>
Ink E-5 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-5.
<Manufacturing of thin film transistor E-5>
The thin film transistor E-5 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-5.
<Evaluation of thin film transistor E-5>
The thin film transistor E-5 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-5.
The evaluation results are shown in Table 1.

(Example 6)
<Manufacturing of compound E-6>
First, 35 mL of dehydrated dichloromethane was added to BTBT (0.50 g, 2.08 mmol) under an argon atmosphere, and the mixture was stirred. The mixture was then cooled to −70 ° C., aluminum chloride (1.16 g, 8.70 mmol) was added, and p-pentylbenzoyl chloride (0.5 mL, 2.46 mmol) was added dropwise. The temperature of the reaction solution was raised to 0 ° C., the mixture was stirred for 4 hours, and then the reaction solution was submerged in water to stop the reaction. Chloroform was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. For purification, the product recovered on a silica gel column (solvent composition: hexane: dichloromethane = 100: 0 to 30:70 yield) was recrystallized from cyclohexane to obtain 0.49 g of 2- (4-pentylbenzoyl) BTBT (4). Yield 57%).

Then, 2M of trimethylsilyldiazomethane solution (1.20 mL, 2.40 mmol) was added to 10 mL of dehydrated tetrahydrofuran under an argon atmosphere, and the mixture was stirred. Further, the mixed solution was cooled to −70 ° C., and a 1.55 M n-butyllithium solution (1.50 mL, 2.33 mmol) was added dropwise to generate a lithium salt of trimethylsilyldiazomethane. After stirring for 30 minutes, a 2- (4-pentylbenzoyl) BTBT (0.49 g, 1.18 mmol) solution containing 7 mL of dehydrated tetrahydrofuran was added to the reaction solution. Then, the reaction solution was heated to room temperature, stirred for 3.5 hours, and then a methanol solution of 10% acetic acid was added to stop the reaction. Dichloromethane was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. For purification, 0.06 g of Compound E-6 was obtained by recrystallizing the product recovered on a silica gel column (the product sprinkled on silica gel and a metal scavenger with cyclohexane heated to 55 ° C.) with acetone. (Yield 13%).

^{1 1} H-NMR (300 MHz, CDCl ₃ ): δ 8.08 (1H, dd, J = 4.4, 3.7 Hz), 7.87 (3H, ddt, J = 19.3, 11.0, 3) .6Hz), 7.61-7.56 (1H, m), 7.49-7.39 (4H, m), 7.19 (2H, d, J = 8.1Hz), 2.63 (2H) , T, J = 7.1Hz), 1.68-1.58 (2H, m), 1.34 (4H, dt, J = 12.6,5.0Hz), 0.90 (3H, dd, J = 9.0, 5.0 Hz).

<Manufacturing of ink E-6>
Ink E-6 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-6.
<Manufacturing of thin film transistor E-6>
The thin film transistor E-6 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-6.
<Evaluation of thin film transistor E-6>
The thin film transistor E-6 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-6.
The evaluation results are shown in Table 1.

(Example 7)
<Manufacturing of compound E-7>
First, 25 mL of dehydrated dichloromethane was added to BTBT (0.50 g, 2.09 mmol) and aluminum chloride (1.16 g, 8.70 mmol) under an argon atmosphere, and the mixture was stirred. The mixture was then cooled to −70 ° C. and p-heptylbenzoyl chloride (0.70 mL, 1.45 mmol) was added dropwise. The temperature of the reaction solution was raised to 0 ° C., the mixture was stirred for 3 hours, and then the reaction solution was submerged in water to stop the reaction. Chloroform was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. For purification, the product recovered on a silica gel column (solvent composition: hexane: dichloromethane = 100: 0 to 30:70 yield) was recrystallized from acetone to obtain 0.39 g of 2- (4-heptylbenzoyl) BTBT (4). Yield 39%).

Then, 2M of trimethylsilyldiazomethane solution (0.85 mL, 2.07 mmol) was added to 5 mL of dehydrated tetrahydrofuran under an argon atmosphere, and the mixture was stirred. Further, the mixed solution was cooled to −70 ° C., and a 1.55 M n-butyllithium solution (1.0 mL, 1.55 mmol) was added dropwise to generate a lithium salt of trimethylsilyldiazomethane. After stirring for 30 minutes, a 2- (4-heptylbenzoyl) BTBT (0.36 g, 0.82 mmol) solution containing 12 mL of dehydrated tetrahydrofuran was added to the reaction solution. Then, the reaction solution was heated to room temperature, stirred for 3 hours, and then a methanol solution of 10% acetic acid was added to stop the reaction. Dichloromethane was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. For purification, the product recovered on a silica gel column (solvent composition is hexane: dichloromethane = 100: 0 to 90:10 yield) is dissolved in acetone heated to 56 ° C., a metal scavenger is added and stirred, and the metal scavenger is filtered off. By removing and recrystallizing from the filtrate, 0.04 g of Compound E-7 was obtained (yield 11%).
^{1 1} H-NMR (300 MHz, CDCl ₃ ): δ 8.09 (1H, d, J = 0.7 Hz), 7.94-7.83 (3H, m), 7.60 (1H, dd, J = 8.3, 1.3Hz), 7.49-7.40 (4H, m), 7.19 (2H, d, J = 8.1Hz), 2.63 (2H, t, J = 7.7Hz) ), 1.60-1.56 (2H, m), 1.31 (8H, m), 0.89 (3H, t, J = J = 6.8Hz).

<Manufacturing of ink E-7>
Ink E-7 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-7.
<Manufacturing of thin film transistor E-7>
The thin film transistor E-7 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-7.
<Evaluation of thin film transistor E-7>
The thin film transistor E-7 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-7.
The evaluation results are shown in Table 1.

(Example 8)
<Manufacturing of compound E-8>
To 2-methylBTBT (0.40 g, 1.66 mmol), 20 mL of dehydrated dichloromethane was added under an argon atmosphere, and the mixture was stirred. The mixture was then cooled to −70 ° C., aluminum chloride (0.90 g, 6.73 mmol) was added, and p-heptylbenzoyl chloride (0.5 mL, 2.10 mmol) was added dropwise. The temperature of the reaction solution was raised to 0 ° C., the mixture was stirred for 2.5 hours, and then the reaction solution was submerged in water to stop the reaction. Chloroform was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. Purification was carried out on a silica gel column (solvent composition: hexane: dichloromethane = 90:10 to 50:50 gradient) to obtain 0.54 g of 2-methyl-7- (4-heptylbenzoyl) BTBT (yield 71%). ..

Then, 2M of trimethylsilyldiazomethane solution (1.20 mL, 2.40 mmol) was added to 4.5 mL of dehydrated tetrahydrofuran under an argon atmosphere, and the mixture was stirred. Further, the mixed solution was cooled to −70 ° C., and a 1.55 M n-butyllithium solution (1.50 mL, 2.33 mmol) was added dropwise to generate a lithium salt of trimethylsilyldiazomethane. After stirring for 30 minutes, a 2-methyl-7- (4-heptylbenzoyl) BTBT (0.54 g, 1.19 mmol) solution containing 21 mL of dehydrated tetrahydrofuran was added to the reaction solution. Then, the reaction solution was heated to room temperature, stirred for 2.5 hours, and then a methanol solution of 10% acetic acid was added to stop the reaction. Chloroform was added thereto, and the mixture was transferred to a separating funnel, and the organic layer was separated and washed with water and brine, dried over magnesium sulfate, and concentrated. For purification, 0.13 g of Compound E-8 was obtained by recrystallizing the product recovered on a silica gel column (the product sprinkled on silica gel and a metal scavenger with cyclohexane heated to 55 ° C.) with acetone. (Yield 24%).
¹ H-NMR (300MHz, CDCl ₃ ): δ 8.05 (1H, t, J = 3.3Hz), 7.81-7.71 (3H, m), 7.57 (1H, dt, J = 10.5Hz, 3.8Hz), 7.46 (2H, t, J = 7.3Hz), 7.29 (1H, d, J = 0.7Hz), 7.17 (2H, t, J = 7) .3Hz), 2.66 (2H, dd, J = 23.3, 16.0Hz), 2.51 (3H, d, J = 6.6Hz), 1.61 (2H, dd, J = 14. 7,7.3Hz), 1.30 (8H, dd, J = 7.2,5.0Hz), 0.89 (3H, t, J = 6.8Hz).

<Manufacturing of ink E-8>
Ink E-8 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-8.
<Manufacturing of thin film transistor E-8>
The thin film transistor E-8 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-8.
<Evaluation of thin film transistor E-8>
The thin film transistor E-8 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-8.
The evaluation results are shown in Table 1.

(Example 9)
<Manufacturing of compound E-9>
Under an argon atmosphere, 500 mL of dry acetone was added to 80.0 g (359 mmol) of 2-bromo-7-hydroxynaphthalene and 149 g (1.08 mol) of potassium carbonate, and the mixture was stirred at room temperature. After dropping 44.9 mL (720 mmol) of iodomethane, the mixture was refluxed for 2 hours. The reaction mixture was cooled to room temperature and 250 mL of water was added. Acetone was distilled off under reduced pressure, 750 mL of water was further added, and the mixture was stirred for 10 minutes. The resulting white precipitate was filtered and the filtrate was washed with 1.5 L of water. The obtained white solid was dried to obtain 71.8 g (yield, 84.4%) of 2-bromo-7-methoxynaphthalene. Then, under an argon atmosphere, the amount was adjusted to 5.42 g (21.1 mmol) of 2-bromo-7-methoxynaphthalene and 0.259 g (1.05 mmol) of dichloro [1,3-bis (diphenylphosphino) propane] nickel (II). 20 mL of dry tetrahydrofuran was added, and the mixture was stirred at −78 ° C. After adding 11.6 mL (23.2 mmol) of a 2M ether solution of n-hexylmagnesium bromide to the reaction solution, the temperature was slowly raised to room temperature. After refluxing for 1 hour, the mixture was cooled to room temperature. After slowly dropping 5 mL of water into the reaction solution, the solid content was removed by filtration through Celite. The filtrate was dried over magnesium sulfate, and the solvent was distilled off. The obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 7/3) to obtain 4.55 g (yield, 82.1%) of 2-hexyl-7-methoxynaphthalene. Then, under an argon atmosphere, 20 mL of dry dichloromethane was added to 4.00 g (16.5 mmol) of 2-hexyl-7-methoxynaphthalene, and the mixture was stirred at −78 ° C. After dropping 28 mL (28 mmol) of a 1 M dichloromethane solution of boron tribromide into the reaction solution, the temperature was raised to room temperature and the mixture was stirred for 1 hour. Water was added to the reaction solution cooled to −78 ° C. again to stop the reaction. After adding 50 mL of dichloromethane and washing with water, the organic phase was dried over magnesium sulfate and the solvent was distilled off to obtain 3.53 g (yield, 91.8%) of 2-hexyl-7-hydroxynaphthalene.
Then, under an argon atmosphere, 1.00 g (4.38 mmol) of 2-hexyl-7-hydroxynaphthalene, 0.701 g (4.38 mmol) of 2-naphthalenethiol, and 0.144 g (0.34 mmol) of bismuth (III) trifluoromethanesulfonate. 218 mmol) was added with 8.8 mL of 1,2-dichloroethane, and the mixture was stirred at 80 ° C. for 16 hours. The reaction mixture was concentrated, and the obtained crude product was separated and purified by silica gel column chromatography (cyclohexane) to obtain 1.36 g (yield, 83.8%) of 7-hexyl-2,2'-binaphthylsulfide.

7-Hexyl-2,2'-binaphthylsulfide 0.500 g (1.35 mmol), trifluoropalladium acetate (II) 0.0449 g (0.135 mmol), silver acetate 0.901 g (5.40 mmol), potassium carbonate 0 2.7 mL of pivalic acid was added to .187 g (1.35 mmol), and the mixture was stirred at 110 ° C. for 16 hours. The reaction mixture was diluted with chloroform and filtered through Celite. The filtrate was concentrated, and the obtained crude product was separated and purified by silica gel column chromatography (hexane) to obtain 0.280 mg (yield, 55.9%) of compound E-9.
^{1 1} H-NMR (300 MHz, CDCl ₃ ): δ8.70 (s, 1H), δ8.68 (s, 1H), δ8.22 (s, 1H), δ8.15 (s, 1H), δ8.06 −8.03 (m, 1H), δ7.98-7.96 (m, 1H), δ7.92-7.89 (m, 1H), δ7.76 (s, 1H), δ7.54-7 .51 (m, 2H), δ7.38 (dd, J = 1.5Hz, 8.4Hz, 1H), δ2.82 (t, J = 7.2Hz, 2H), δ1.76-1.70 ( m, 2H), δ1.36-1.24 (m, 6H), δ0.90 (t, J = 6.6Hz, 3H).

<Manufacturing of ink E-9>
Ink E-9 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-9.
<Manufacturing of thin film transistor E-9>
The thin film transistor E-9 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-9.
<Evaluation of thin film transistor E-9>
The thin film transistor E-9 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-9.
The evaluation results are shown in Table 1.

(Example 10)
<Manufacturing of compound E-10>
Compound E-10 (yield, 64.3%) was obtained in accordance with Example 9 except that n-hexylmagnesium bromide was changed to n-octylmagnesium bromide in Example 9.

^{1 1} H-NMR (300 MHz, CDCl ₃ ): δ8.69 (s, 1H), δ8.67 (s, 1H), δ8.21 (s, 1H), δ8.14 (s, 1H), δ8.09 −8.04 (m, 1H), δ8.03-7.98 (m, 1H), δ7.91-7.89 (m, 1H), δ7.66 (s, 1H), δ7.56-7 .48 (m, 2H), δ7.38 (dd, J = 1.5Hz, 8.4Hz, 1H), δ2.82 (t, J = 7.2Hz, 2H), δ1.77-1.69 ( m, 2H), δ1.36-1.24 (m, 10H), δ0.88 (t, J = 6.6Hz, 3H).
<Manufacturing of ink E-10>
Ink E-10 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-10.
<Manufacturing of thin film transistor E-10>
The thin film transistor E-10 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-10.
<Evaluation of thin film transistor E-10>
The thin film transistor E-10 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-10.
The evaluation results are shown in Table 1.

(Example 11)
<Manufacturing of compound E-11>

Synthesized in a 2L three-necked flask connected with an argon balloon by changing R of the compound represented by (1ab) to H by the method described in Advanced Materials, 2009, Vol. 21, pp. 213-216. Dithienobenzodithiophene (3.02 g, 10 mmol) obtained in the above procedure was added to carry out argon substitution. Chloroform (1500 mL, manufactured by Kanto Chemical Co., Inc.) was added and dissolved, and then the internal temperature was heated to 60 ° C. A solution prepared by dissolving N-bromosuccinimide (NBS, 1.86 g, 10.5 mmol, manufactured by Kishida Chemical Co., Ltd.) in chloroform (150 mL) was added dropwise. After stirring for 30 minutes while maintaining 60 ° C., the mixture was cooled to room temperature (the reaction solution turned yellow). The slightly precipitated solid (mainly bromine disubstituted product) is removed by filtration, 100 mL of saturated aqueous sodium thiosulfate solution is added to the filtrate, the organic layer is separated by liquid separation operation, dried over anhydrous magnesium sulfate, and filtered. After that, the solvent was distilled off. The obtained pale yellow solid was dried to obtain 2.8 g (7.3 mmol, yield 73%) of α-monobromodithioenobenzothiophene, which was the target product.

Α-monobromodithienobenzothiophene (2.67 g, 7.0 mmol) obtained by the method described in the above example and tetrakis (triphenylphosphine) palladium (242 mg) were placed in a 500 mL three-necked flask connected with an argon balloon. , 0.21 mmol, manufactured by Tokyo Kasei Co., Ltd.) and copper iodide (40 mg, 0.21 mmol, manufactured by Kanto Chemical Co., Inc.) were added to carry out argon substitution. After adding dry toluene (150 mL, manufactured by Kanto Chemical Co., Inc.), the internal temperature was heated to 70 ° C. N, N-diisopropylethylamine (9.8 mL, 70 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) and 1-hexyne (2.4 mL, 21 mmol, manufactured by Tokyo Kasei Co., Ltd.) were added dropwise, and the mixture was stirred for 12 hours while maintaining 70 ° C. It was cooled to room temperature (the reaction solution turned black). After adding 100 mL of ion-exchanged water to the reaction solution, the organic layer is separated by a liquid separation operation, dried and filtered over anhydrous magnesium sulfate, and then stirred at room temperature for 45 minutes using a metal scavenger to remove transition metals and filtered. Later the solvent was distilled off. The obtained crude black product is purified by silica gel column chromatography (hexane, hexane: chloroform = 98: 2) and dried to obtain the desired α-mono (hex-1-inyl) dithienobenzothiophene. It was obtained as a pale yellow solid at 1.04 g (2.7 mmol, yield 39%).

In a 1 L two-necked flask connected with a hydrogen balloon, α-mono (hex-1-inyl) dithienobenzothiophene (956 mg, 2.5 mmol) obtained by the method described in the above example and palladium carbon (300 mg, 300 mg, 50% wet) was added to carry out hydrogen substitution. After adding THF (100 mL, manufactured by Kanto Chemical Co., Inc.), the mixture was vigorously stirred at room temperature for 48 hours. The reaction solution was filtered through Celite to remove the transition metal, and the solvent was distilled off. The obtained pale yellow crude product was purified by silica gel column chromatography (hexane, hexane: chloroform = 98: 2) and recrystallized by heating using a mixed solvent of acetonitrile: toluene = 90:10. Compound E-11, which is a product, was obtained as a colorless solid at 620 mg (1.6 mmol, yield 64%). Further, by repeating normal phase silica gel column chromatography (hexane / chloroform), reverse phase octadecylsilyl chromatography (acetonitrile / toluene), and recrystallization (acetonitrile / toluene), the semiconductor characteristics (electric field effect mobility) are evaluated. 120 mg of compound E-11 having sufficient purity has been obtained.
^{1 1} H-NMR (300 MHz, CDCl ₃ ): δppm = 0.90 (t, ³ J _H-H = 7.2 Hz, 3 H), 1.3-1.5 (m.95 (t, ³ J _{H-) H} = 7.2Hz, 2H), 7.01 (s, 1H), 7.32 (d, ³ J _H-H = 5.1 Hz, 1 H), 7.51 (d, ³ J _H-H = 5) .1Hz, 1H), 8.20 (s, 1H), 8.27 (s, 1H).
<Manufacturing of ink E-11>
Ink E-11 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-11.
<Manufacturing of thin film transistor E-11>
The thin film transistor E-11 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-11.
<Evaluation of thin film transistor E-11>
The thin film transistor E-11 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-11.
The evaluation results are shown in Table 1.

(Example 12)
<Manufacturing of compound E-12>

Compound E-11 (270 mg, 0.7 mmol) obtained by the method described in Example 11 was added to a 300 mL three-necked flask to which an argon balloon was connected to perform argon substitution. After adding dry THF (30 mL, manufactured by Kanto Chemical Co., Inc.), the mixture was cooled to −78 ° C. and stirred for 5 minutes. Normal butyllithium (0.65 mL, 1.0 mmol, about 1.6 M hexane solution, manufactured by Kanto Chemical Co., Inc.) was added, and the mixture was stirred for 30 minutes while maintaining the internal temperature at -78 ° C (the reaction solution turned pale red). .. Iodomethane (0.07 mL, 1.0 mmol, manufactured by Tokyo Kasei Co., Ltd.) was added, and the mixture was stirred while raising the temperature to room temperature over 1 hour (the reaction solution turned pale yellow). After adding 20 mL of a saturated aqueous solution of ammonium chloride, the organic layer was separated by a liquid separation operation using toluene, dried over anhydrous magnesium sulfate, filtered, and then the solvent was distilled off. The obtained crude yellow product was purified by silica gel column chromatography (hexane, hexane: toluene = 99: 1), recrystallized by heating using a mixed solvent of acetonitrile: toluene = 90:10, and dried. The target compound E-12 was obtained as a colorless solid at 150 mg (0.37 mmol, yield 53%). Further, by repeating normal phase silica gel column chromatography (hexane / toluene), reverse phase octadecylsilyl chromatography (acetonitrile / toluene), and recrystallization (acetonitrile / toluene), the semiconductor characteristics (electric field effect mobility) are evaluated. 50 mg of compound E-12 having a sufficient purity is obtained.
^{1 1} H-NMR (300 MHz, CDCl ₃ ): δppm = 0.90 (t, ³ _JH-H = 6.9 Hz, 3H), 1.3-1.5 (m, 6H), 1.76 (m) , 2H), 2.64 (d, ⁴ J _H-H = 0.9 Hz, 3 H), 2.94 (t, ³ J _H-H = 7.5 Hz, 2 H), 6.98 (d, ⁴ J) _HH = 0.9Hz, 1H), 6.99 (s, 1H), 8.15 (s, 1H + 1H).
<Manufacturing of ink E-12>
Ink E-12 was produced in the same manner as in Example 1 except that compound E-1 was converted to compound E-12.
<Manufacturing of thin film transistor E-12>
The thin film transistor E-12 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-12.
<Evaluation of thin film transistor E-12>
The thin film transistor E-12 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-12.
The evaluation results are shown in Table 1.

(Example 13)
<Manufacturing of ink E-13>
Ink E-13 was produced in the same manner as in Example 1 except that the ink solvent was changed from butyrophenone (boiling point 222 degrees, surface tension 35.3 mN / m).
<Manufacturing of thin film transistor E-13>
The thin film transistor E-13 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-13.
<Evaluation of thin film transistor E-13>
The thin film transistor E-13 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-13.
The evaluation results are shown in Table 1.

(Example 14)
<Manufacturing of ink E-14>
Ink E-14 was produced in the same manner as in Example 2 except that the ink solvent was changed from butoxybenzene to butyrophenone.
<Manufacturing of thin film transistor E-14>
The thin film transistor E-14 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-14.
<Evaluation of thin film transistor E-14>
The thin film transistor E-14 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-14.
The evaluation results are shown in Table 1.

(Example 15)
<Manufacturing of ink E-15>
Ink E-15 was produced in the same manner as in Example 3 except that the ink solvent was changed from butoxybenzene to butyrophenone.
<Manufacturing of thin film transistor E-15>
The thin film transistor E-15 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-15.
<Evaluation of thin film transistor E-15>
The thin film transistor E-15 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-15.
The evaluation results are shown in Table 1.

(Example 16)
<Manufacturing of ink E-16>
Ink E-16 was produced in the same manner as in Example 4 except that the ink solvent was changed from butoxybenzene to butyrophenone.
<Manufacturing of thin film transistor E-16>
The thin film transistor E-16 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-16.
<Evaluation of thin film transistor E-16>
The thin film transistor E-16 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-16.
The evaluation results are shown in Table 1.

(Example 17)
<Manufacturing of ink E-17>
Ink E-17 was produced in the same manner as in Example 5 except that the ink solvent was changed from butoxybenzene to butyrophenone.
<Manufacturing of thin film transistor E-17>
The thin film transistor E-17 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-17.
<Evaluation of thin film transistor E-17>
The thin film transistor E-17 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-17.
The evaluation results are shown in Table 1.

(Example 18)
<Manufacturing of ink E-18>
Ink E-18 was produced in the same manner as in Example 1 except that the ink solvent was changed from butoxybenzene to 1,3,5-triethylbenzene (boiling point 215 degrees, surface tension 24.7 mN / m).
<Manufacturing of thin film transistor E-18>
The thin film transistor E-18 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-18.
<Evaluation of thin film transistor E-18>
The thin film transistor E-18 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-18.
The evaluation results are shown in Table 1.

(Example 19)
<Manufacturing of ink E-19>
Ink E-19 was produced in the same manner as in Example 2 except that the ink solvent was changed from butoxybenzene to 1,3,5-triethylbenzene.
<Manufacturing of thin film transistor E-19>
The thin film transistor E-19 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-19.
<Evaluation of thin film transistor E-19>
The thin film transistor E-19 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-19.
The evaluation results are shown in Table 1.

(Example 20)
<Manufacturing of ink E-20>
Ink E-20 was produced in the same manner as in Example 3 except that the ink solvent was changed from butoxybenzene to 1,3,5-triethylbenzene.
<Manufacturing of thin film transistor E-20>
The thin film transistor E-20 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-20.
<Evaluation of thin film transistor E-20>
The thin film transistor E-20 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-20.
The evaluation results are shown in Table 1.

(Example 21)
<Manufacturing of ink E-21>
Ink E-21 was produced in the same manner as in Example 4 except that the ink solvent was changed from butoxybenzene to 1,3,5-triethylbenzene.
<Manufacturing of thin film transistor E-21>
The thin film transistor E-21 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-21.
<Evaluation of thin film transistor E-21>
The thin film transistor E-21 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-21.
The evaluation results are shown in Table 1.

(Example 22)
<Manufacturing of ink E-22>
Ink E-22 was produced in the same manner as in Example 5 except that the ink solvent was changed from butoxybenzene to 1,3,5-triethylbenzene.
<Manufacturing of thin film transistor E-22>
The thin film transistor E-22 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-22.
<Evaluation of thin film transistor E-22>
The thin film transistor E-22 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-22.
The evaluation results are shown in Table 1.

(Example 23)
<Manufacturing of ink E-23>
Ink E-23 was produced in the same manner as in Example 1 except that the ink solvent was changed from butoxybenzene to isophorone (boiling point 215 ° C., surface tension 31.4).
<Manufacturing of thin film transistor E-23>
The thin film transistor E-23 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-23.
<Evaluation of thin film transistor E-23>
The thin film transistor E-23 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-23.
The evaluation results are shown in Table 1.

(Example 24)
<Manufacturing of ink E-24>
Ink E-24 was produced in the same manner as in Example 2 except that the ink solvent was changed from butoxybenzene to isophorone.
<Manufacturing of thin film transistor E-24>
The thin film transistor E-24 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-24.
<Evaluation of thin film transistor E-24>
The thin film transistor E-24 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-24.
The evaluation results are shown in Table 1.

(Example 25)
<Manufacturing of ink E-25>
Ink E-25 was produced in the same manner as in Example 3 except that the ink solvent was changed from butoxybenzene to isophorone.
<Manufacturing of thin film transistor E-25>
The thin film transistor E-25 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-25.
<Evaluation of thin film transistor E-25>
The thin film transistor E-25 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-25.
The evaluation results are shown in Table 1.

(Example 26)
<Manufacturing of ink E-26>
Ink E-26 was produced in the same manner as in Example 4 except that the ink solvent was changed from butoxybenzene to isophorone.
<Manufacturing of thin film transistor E-26>
The thin film transistor E-26 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-26.
<Evaluation of thin film transistor E-26>
The thin film transistor E-26 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-26.
The evaluation results are shown in Table 1.

(Example 27)
<Manufacturing of ink E-27>
Ink E-27 was produced in the same manner as in Example 5 except that the ink solvent was changed from butoxybenzene to isophorone.
<Manufacturing of thin film transistor E-27>
The thin film transistor E-27 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-27.
<Evaluation of thin film transistor E-27>
The thin film transistor E-27 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-27.
The evaluation results are shown in Table 1.

(Example 28)
<Manufacturing of thin film transistor E-28>
A test element of a thin film transistor having a BGBC (bottom gate bottom contact) type structure was manufactured by the following procedure.
First, an electrode having a thickness of 90 nm was formed as a gate electrode on a non-alkali glass having a thickness of 0.7 mm by a sputtering method using chromium.
Next, as the gate insulating film layer, the resin ink produced according to the method of Comparative Example 2 of Publication No. 2010-265423 was patterned on the support on which the gate electrode was formed by the reverse printing method, and the insulation having a thickness of about 700 nm was obtained. A membrane layer was formed. The surface roughness Ra of the insulating film layer formed by the reverse printing method was 10 nm. It is a value larger than Ra of the insulating film formed by the spin coating method described above, and it can be seen that the surface is rough. Further, a surface SEM image of the insulating film layer formed by the reverse printing method is shown in FIG. Compared with the surface SEM image of the insulating film layer formed by the spin coating method shown in FIG. 3, it is clear from the surface SEM image that the surface of the insulating film layer formed by the reverse printing method is rough.
Next, gold was vacuum-deposited on the insulating film layer on which gold was previously formed as a source electrode and a drain electrode to form a gold electrode having a thickness of 30 nm. The channel length between the source electrode and the drain electrode was 25 μm. Next, a fluororesin was used as the partition wall layer, and a rectangular partition wall layer was formed by an inkjet method so as to surround the channel region between the source electrode and the drain electrode described above.
Next, as an organic semiconductor thin film, ink E-1 is dropped onto the channel portion between the source electrode and the drain electrode formed earlier by an inkjet method, and after the film is formed, an element is used using a hot plate (to remove the solvent). Was heat-treated at 80 ° C. for 10 minutes to form an organic semiconductor thin film.
In this way, the thin film transistor E-28 was manufactured.
<Evaluation of thin film transistor E-28>
The thin film transistor E-28 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-28.
The evaluation results are shown in Table 1.

(Example 29)
<Manufacturing of thin film transistor E-29>
The thin film transistor E-29 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-2.
<Evaluation of thin film transistor E-29>
The thin film transistor E-29 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-29.
The evaluation results are shown in Table 1.

(Example 30)
<Manufacturing of thin film transistor E-30>
The thin film transistor E-30 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-3.
<Evaluation of thin film transistor E-30>
The thin film transistor E-30 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-30.
The evaluation results are shown in Table 1.

(Example 31)
<Manufacturing of thin film transistor E-31>
The thin film transistor E-31 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-4.
<Evaluation of thin film transistor E-31>
The thin film transistor E-31 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-31.
The evaluation results are shown in Table 1.

(Example 32)
<Manufacturing of thin film transistor E-32>
The thin film transistor E-32 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-5.
<Evaluation of thin film transistor E-32>
The thin film transistor E-32 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-32.
The evaluation results are shown in Table 1.

(Example 33)
<Manufacturing of thin film transistor E-33>
The thin film transistor E-33 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-6.
<Evaluation of thin film transistor E-33>
The thin film transistor E-33 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-33.
The evaluation results are shown in Table 1.

(Example 34)
<Manufacturing of thin film transistor E-34>
The thin film transistor E-34 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-7.
<Evaluation of thin film transistor E-34>
The thin film transistor E-34 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-34.
The evaluation results are shown in Table 1.

(Example 35)
<Manufacturing of thin film transistor E-35>
The thin film transistor E-35 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-8.
<Evaluation of thin film transistor E-35>
The thin film transistor E-35 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-35.
The evaluation results are shown in Table 1.

(Example 36)
<Manufacturing of thin film transistor E-36>
The thin film transistor E-36 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-13.
<Evaluation of thin film transistor E-36>
The thin film transistor E-36 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-36.
The evaluation results are shown in Table 1.

(Example 37)
<Manufacturing of thin film transistor E-37>
The thin film transistor E-37 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-14.
<Evaluation of thin film transistor E-37>
The thin film transistor E-37 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-37.
The evaluation results are shown in Table 1.

(Example 38)
<Manufacturing of thin film transistor E-38>
The thin film transistor E-38 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-15.
<Evaluation of thin film transistor E-38>
The thin film transistor E-38 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-38.
The evaluation results are shown in Table 1.

(Example 39)
<Manufacturing of thin film transistor E-39>
The thin film transistor E-39 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-16.
<Evaluation of thin film transistor E-39>
The thin film transistor E-39 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-39.
The evaluation results are shown in Table 1.

(Example 40)
<Manufacturing of thin film transistor E-40>
The thin film transistor E-40 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-17.
<Evaluation of thin film transistor E-40>
The thin film transistor E-40 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-40.
The evaluation results are shown in Table 1.

(Example 41)
<Manufacturing of thin film transistor E-41>
A test element of a thin film transistor having a BGBC (bottom gate bottom contact) type structure was manufactured by the following procedure.
First, an electrode having a thickness of 90 nm was formed as a gate electrode on a non-alkali glass having a thickness of 0.7 mm by a sputtering method using chromium.
Next, as a gate insulating film layer, a resin ink produced according to the method of Comparative Example 2 of Publication No. 2010-265423 was formed on a support on which a gate electrode was formed by an inversion printing method, and an insulating film layer having a thickness of about 700 nm was formed. Was formed.
Next, as the source electrode and the drain electrode, the thickness is increased by the reverse printing method according to the method described in Example (Preparation of the electrode by the letterpress reversal printing method) of Japanese Patent Application Laid-Open No. 2016-058448 on the previously formed insulating film layer. A 100 nm silver electrode was formed. The surface roughness Ra of the electrode formed by the reverse printing method was 15 nm. It is a value larger than Ra of the electrode formed by the vacuum vapor deposition method described above, and it can be seen that the surface is rough. Further, a surface SEM image of the electrode formed by the reverse printing method is shown in FIG. Compared with the surface SEM image of the electrode formed by the vacuum vapor deposition method shown in FIG. 4, it is clear from the surface SEM image that the surface of the electrode formed by the reverse printing method is rough. The channel length between the source electrode and the drain electrode was 20 μm.
Next, a fluororesin was used as the partition wall layer, and a rectangular partition wall layer was formed by an inkjet method so as to surround the channel region between the source electrode and the drain electrode described above.
Next, as an organic semiconductor thin film, ink E-1 is dropped onto the channel portion between the source electrode and the drain electrode formed earlier by an inkjet method, and after the film is formed, an element is used using a hot plate (to remove the solvent). Was heat-treated at 80 ° C. for 10 minutes to form an organic semiconductor thin film.
In this way, the thin film transistor E-41 was manufactured.
<Evaluation of thin film transistor E-41>
The thin film transistor E-41 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-41.
The evaluation results are shown in Table 1.

(Example 42)
<Manufacturing of thin film transistor E-42>
The thin film transistor E-42 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-2.
<Evaluation of thin film transistor E-42>
The thin film transistor E-42 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-42.
The evaluation results are shown in Table 1.

Example 43)
<Manufacturing of thin film transistor E-43>
The thin film transistor E-43 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-3.
<Evaluation of thin film transistor E-43>
The thin film transistor E-43 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-43.
The evaluation results are shown in Table 1.

(Example 44)
<Manufacturing of thin film transistor E-44>
The thin film transistor E-44 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-4.
<Evaluation of thin film transistor E-44>
The thin film transistor E-44 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-44.
The evaluation results are shown in Table 1.

(Example 45)
<Manufacturing of thin film transistor E-45>
The thin film transistor E-45 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-5.
<Evaluation of thin film transistor E-45>
The thin film transistor E-45 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-45.
The evaluation results are shown in Table 1.

(Example 46)
<Manufacturing of thin film transistor E-46>
The thin film transistor E-46 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-6.
<Evaluation of thin film transistor E-46>
The thin film transistor E-46 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-46.
The evaluation results are shown in Table 1.

(Example 47)
<Manufacturing of thin film transistor E-47>
The thin film transistor E-47 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-7.
<Evaluation of thin film transistor E-47>
The thin film transistor E-47 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-47.
The evaluation results are shown in Table 1.

(Example 48)
<Manufacturing of thin film transistor E-48>
The thin film transistor E-48 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-8.
<Evaluation of thin film transistor E-48>
The thin film transistor E-48 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-48.
The evaluation results are shown in Table 1.

(Example 49)
<Manufacturing of thin film transistor E-49>
The thin film transistor E-49 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-13.
<Evaluation of thin film transistor E-49>
The thin film transistor E-49 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-49.
The evaluation results are shown in Table 1.

(Example 50)
<Manufacturing of thin film transistor E-50>
The thin film transistor E-50 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-14.
<Evaluation of thin film transistor E-50>
The thin film transistor E-50 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-50.
The evaluation results are shown in Table 1.

(Example 51)
<Manufacturing of thin film transistor E-51>
The thin film transistor E-51 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-15.
<Evaluation of thin film transistor E-51>
The thin film transistor E-51 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-51.
The evaluation results are shown in Table 1.

(Example 52)
<Manufacturing of thin film transistor E-52>
The thin film transistor E-52 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-16.
<Evaluation of thin film transistor E-52>
The thin film transistor E-52 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-52.
The evaluation results are shown in Table 1.

(Example 53)
<Manufacturing of thin film transistor E-53>
The thin film transistor E-53 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-17.
<Evaluation of thin film transistor E-53>
The thin film transistor E-53 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-53.
The evaluation results are shown in Table 1.

(Example 54)
<Manufacturing of ink E-54>
Compound E-1, polystyrene and butoxybenzene were mixed at a weight ratio of 4: 1: 995 to produce ink E-54.
<Manufacturing of thin film transistor E-54>
The thin film transistor E-54 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-54.
<Evaluation of thin film transistor E-54>
The thin film transistor E-54 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-54.
The evaluation results are shown in Table 1.

(Example 55)
<Manufacturing of ink E-55>
Ink E-55 was produced in the same manner as in Example 54 except that compound E-1 was converted to compound E-2.
<Manufacturing of thin film transistor E-55>
The thin film transistor E-55 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-55.
<Evaluation of thin film transistor E-55>
The thin film transistor E-55 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-55.
The evaluation results are shown in Table 1.

(Example 56)
<Manufacturing of ink E-56>
Ink E-56 was produced in the same manner as in Example 54 except that compound E-1 was converted to compound E-3.
<Manufacturing of thin film transistor E-56>
The thin film transistor E-56 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-56.
<Evaluation of thin film transistor E-56>
The thin film transistor E-56 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-56.
The evaluation results are shown in Table 1.

(Example 57)
<Manufacturing of ink E-57>
Ink E-57 was produced in the same manner as in Example 54 except that compound E-1 was converted to compound E-4.
<Manufacturing of thin film transistor E-57>
The thin film transistor E-57 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-57.
<Evaluation of thin film transistor E-57>
The thin film transistor E-57 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-57.
The evaluation results are shown in Table 1.

(Example 58)
<Manufacturing of ink E-58>
Ink E-58 was produced in the same manner as in Example 54 except that compound E-1 was converted to compound E-5.
<Manufacturing of thin film transistor E-58>
The thin film transistor E-58 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-58.
<Evaluation of thin film transistor E-58>
The thin film transistor E-58 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-58.
The evaluation results are shown in Table 1.

(Example 59)
<Manufacturing of ink E-59>
Ink E-59 was produced in the same manner as in Example 54 except that polystyrene was changed to polymethylmethacrylate.
<Manufacturing of thin film transistor E-59>
The thin film transistor E-59 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-59.
<Evaluation of thin film transistor E-59>
The thin film transistor E-59 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-59.
The evaluation results are shown in Table 1.

(Example 60)
<Manufacturing of ink E-60>
Ink E-60 was produced in the same manner as in Example 59 except that compound E-1 was converted to compound E-2.
<Manufacturing of thin film transistor E-60>
The thin film transistor E-60 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-60.
<Evaluation of thin film transistor E-60>
The thin film transistor E-60 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-60.
The evaluation results are shown in Table 1.

(Example 61)
<Manufacturing of ink E-61>
Ink E-61 was produced in the same manner as in Example 59 except that compound E-1 was converted to compound E-3.
<Manufacturing of thin film transistor E-61>
The thin film transistor E-61 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-61.
<Evaluation of thin film transistor E-61>
The thin film transistor E-61 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-61.
The evaluation results are shown in Table 1.

(Example 62)
<Manufacturing of ink E-62>
Ink E-62 was produced in the same manner as in Example 59 except that compound E-1 was converted to compound E-4.
<Manufacturing of thin film transistor E-62>
The thin film transistor E-62 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-62.
<Evaluation of thin film transistor E-62>
The thin film transistor E-62 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-62.
The evaluation results are shown in Table 1.

(Example 63)
<Manufacturing of ink E-63>
Ink E-63 was produced in the same manner as in Example 59 except that compound E-1 was converted to compound E-5.
<Manufacturing of thin film transistor E-63>
The thin film transistor E-63 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink E-63.
<Evaluation of thin film transistor E-63>
The thin film transistor E-63 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-63.
The evaluation results are shown in Table 1.

(Example 64)
<Manufacturing of thin film transistor E-64>
The thin film transistor E-64 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-59.
<Evaluation of thin film transistor E-64>
The thin film transistor E-64 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-64.
The evaluation results are shown in Table 1.

(Example 65)
<Manufacturing of thin film transistor E-65>
The thin film transistor E-65 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-60.
<Evaluation of thin film transistor E-65>
The thin film transistor E-65 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-65.
The evaluation results are shown in Table 1.

(Example 66)
<Manufacturing of thin film transistor E-66>
The thin film transistor E-66 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-61.
<Evaluation of thin film transistor E-66>
The thin film transistor E-66 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-66.
The evaluation results are shown in Table 1.

(Example 67)
<Manufacturing of thin film transistor E-67>
The thin film transistor E-67 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-62.
<Evaluation of thin film transistor E-67>
The thin film transistor E-67 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-67.
The evaluation results are shown in Table 1.

(Example 68)
<Manufacturing of thin film transistor E-68>
The thin film transistor E-68 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink E-63.
<Evaluation of thin film transistor E-68>
The thin film transistor E-68 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-68.
The evaluation results are shown in Table 1.

(Example 69)
<Manufacturing of thin film transistor E-69>
The thin film transistor E-69 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-60.
<Evaluation of thin film transistor E-69>
The thin film transistor E-69 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-69.
The evaluation results are shown in Table 1.

(Example 70)
<Manufacturing of thin film transistor E-69>
The thin film transistor E-70 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink E-62.
<Evaluation of thin film transistor E-70>
The thin film transistor E-70 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor E-70.
The evaluation results are shown in Table 1.

(Comparative Example 1)
<Manufacturing of ink C-1>
Ink C-1 was produced in the same manner as in Example 1 except that the ink solvent was changed from butoxybenzene to p-xylene (boiling point 139 ° C., surface tension 27.8 mN / m).
<Manufacturing of thin film transistor C-1>
The thin film transistor C-1 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-1.
<Evaluation of thin film transistor C-1>
The thin film transistor C-1 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-1.
The evaluation results are shown in Table 1.

(Comparative Example 2)
<Manufacturing of ink C-2>
Ink C-2 was produced in the same manner as in Example 2 except that the ink solvent was changed from butoxybenzene to mesitylene (boiling point 165 ° C., surface tension 28.2 mN / m).
<Manufacturing of thin film transistor C-2>
The thin film transistor C-2 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-2.
<Evaluation of thin film transistor C-2>
The thin film transistor C-2 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-2.
The evaluation results are shown in Table 1.

(Comparative Example 3)
<Manufacturing of ink C-3>
Ink C-3 was produced in the same manner as in Example 3 except that the ink solvent was changed from butoxybenzene to 3-phenoxytoluene (boiling point 272 ° C., surface tension 38.1 mN / m).
<Manufacturing of thin film transistor C-3>
The thin film transistor C-3 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-3.
<Evaluation of thin film transistor C-3>
The thin film transistor C-3 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-3.
The evaluation results are shown in Table 1.

(Comparative Example 4)
<Manufacturing of ink C-4>
Ink C-4 was produced in the same manner as in Example 4 except that the ink solvent was changed from butoxybenzene to 1-methylnaphthalene (boiling point 242 ° C., surface tension 39.7 mN / m).
<Manufacturing of thin film transistor C-4>
The thin film transistor C-4 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-4.
<Evaluation of thin film transistor C-4>
The thin film transistor C-4 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-4.
The evaluation results are shown in Table 1.

(Comparative Example 5)
<Manufacturing of ink C-5>
Ink C-5 was produced in the same manner as in Example 1 except that compound E-1 was changed to compound C-5.

<Manufacturing of thin film transistor C-5>
The thin film transistor C-5 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-5.
<Evaluation of thin film transistor C-5>
The thin film transistor C-5 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-5.
The evaluation results are shown in Table 1.

(Comparative Example 6)
<Manufacturing of ink C-6>
Ink C-6 was produced in the same manner as in Example 1 except that compound E-1 was changed to compound C-6.

<Manufacturing of thin film transistor C-6>
The thin film transistor C-6 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-6.
<Evaluation of thin film transistor C-6>
The thin film transistor C-6 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-6.
The evaluation results are shown in Table 1.

(Comparative Example 7)
<Manufacturing of thin film transistor C-7>
The thin film transistor C-7 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink C-2.
<Evaluation of thin film transistor C-7>
The thin film transistor C-7 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-7.
The evaluation results are shown in Table 1.

(Comparative Example 8)
<Manufacturing of thin film transistor C-8>
The thin film transistor C-8 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink C-4.
<Evaluation of thin film transistor C-8>
The thin film transistor C-8 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-8.
The evaluation results are shown in Table 1.

(Comparative Example 9)
<Manufacturing of thin film transistor C-9>
The thin film transistor C-9 was manufactured in the same manner as in Example 28 except that the ink E-1 was changed to the ink C-2.
<Evaluation of thin film transistor C-9>
The thin film transistor C-9 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-9.
The evaluation results are shown in Table 1.

(Comparative Example 10)
<Manufacturing of thin film transistor C-10>
The thin film transistor C-10 was manufactured in the same manner as in Example 1 except that the ink E-1 was changed to the ink C-4.
<Evaluation of thin film transistor C-10>
The thin film transistor C-10 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-10.
The evaluation results are shown in Table 1.

(Comparative Example 11)
<Manufacturing of thin film transistor C-11>
The thin film transistor C-11 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink C-5.
<Evaluation of thin film transistor C-11>
The thin film transistor C-11 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-11.
The evaluation results are shown in Table 1.

(Comparative Example 12)
<Manufacturing of thin film transistor C-12>
The thin film transistor C-12 was manufactured in the same manner as in Example 41 except that the ink E-1 was changed to the ink C-6.
<Evaluation of thin film transistor C-12>
The thin film transistor C-12 was evaluated in the same manner as in Example 1 except that the thin film transistor E-1 was changed to the thin film transistor C-12.
The evaluation results are shown in Table 1.

As shown in the table, the thin film transistor using the inkjet ink for forming an organic semiconductor thin film of the present invention exhibits excellent field effect mobility, and the variation in field effect mobility is small. On the other hand, the thin film transistors C-1 to C-10 according to Comparative Examples 1 to 10, which do not use the inkjet ink for forming an organic semiconductor thin film of the present invention, are the thin film transistors E-1 to thin film transistors E-1 to the thin film transistors according to the examples. The above characteristics are inferior to those of E-69.
Further, the thin film transistor using the ink of the present invention shows excellent field effect mobility even when the gate insulating layer and the source and drain electrodes as the base layer are formed by a printing method, and further, the field effect mobility varies. Is small. In general, it is known that if the base is rough, the above characteristics are significantly deteriorated. The results of verification 1 and verification 2 which are examples of clarifying this are shown below.

(Verification 1)
With the thin film transistor S-1 produced by forming a gate electrode, an insulating film layer, a source electrode and a drain electrode according to the method described in Example 1 and further forming dinaphthothienothiophene as an organic semiconductor layer by a vacuum vapor deposition method. , A thin film transistor S- produced by forming a gate electrode, an insulating film layer, a source electrode and a drain electrode according to the method described in Example 28, and further forming dinaphthothienothiophene as an organic semiconductor layer by a vacuum deposition method. 2. A thin film transistor produced by forming a gate electrode, an insulating film layer, a source electrode and a drain electrode according to the method described in Example 41, and further forming dinaphthothienothiophene as an organic semiconductor layer by a vacuum deposition method. Ten S-3s were produced for each. The average value of the field effect mobility and its variation are as follows: thin film transistor S-1: field effect mobility μ = 0.1, variation CV = 32% / thin film transistor S-2: field effect mobility μ = 0.02, variation CV = 66% / Thin film transistor S-3: Field effect mobility μ = 0.004, variation CV = 73%.

(Verification 2)
A gate electrode, an insulating film layer, a source electrode and a drain electrode are formed according to the method described in Example 1, and 6,13-bis (triisopropylsilylethynyl) pentacene is further formed as an organic semiconductor layer by a spin coating method. A gate electrode, an insulating film layer, a source electrode and a drain electrode were formed from the thin film S-4 produced by the above method according to the method described in Example 28, and 6,13-bis (triisopropylsilylethynyl) was further formed as an organic semiconductor layer. A gate electrode, an insulating film layer, a source electrode and a drain electrode are formed with the thin film S-5 produced by forming a film of pentacene by a spin coating method, and further, as an organic semiconductor layer, 6 , 13-Bis (triisopropylsilylethynyl) pentacene was formed by forming a film by a spin coating method to produce 10 thin films S-6 each. The average value of the field effect mobility and its variation are as follows: thin film transistor S-4: field effect mobility μ = 0.1, variation CV = 43% / thin film transistor S-5: field effect mobility μ = 0.05, variation CV = 76% / Thin film transistor S-6: Field effect mobility μ <0.01, variation CV = 117%.

However, when the ink of the present invention is used,
(Case 1) Thin film transistor in which the gate insulating layer is formed by a spin coating method and the source and drain electrodes are formed by a vacuum vapor deposition method (Case 2) The gate insulating layer is formed by a printing method, and the source and drain electrodes are formed by a vacuum vapor deposition method. When three types of thin film transistors formed (Case 3), a gate insulating layer and a source and a drain electrode formed by a printing method, are compared, (Case 2) a source and a drain electrode are formed by a vacuum vapor deposition method, and a gate insulating layer is formed. The characteristics of the thin film transistor formed by the spin coating method and (Case 3) the gate insulating layer and the source and the drain electrode formed by the printing method are as follows: (Case 1) the gate insulating layer is formed by the spin coating method, and the source and the drain electrode are formed by the printing method. Although it is slightly inferior to the characteristics of a thin film transistor in which the drain electrode is formed by a vacuum vapor deposition method, it exhibits almost the same characteristics. (Specifically, Example 2 and Example 29 and Example 42, Example 4 and Example 31 and Example 44, Example 69 and Example 60 and Example 65, and Example 70 and Example 62. And Example 67.)

From this result, the ink of the present invention shows excellent field effect mobility even when the gate insulating layer and the source and drain electrodes to be the base layer are formed by the printing method, and the thin film transistor has a small variation in the field effect mobility. Was shown to be capable of manufacturing. This result can be said to be a characteristic effect of the ink of the present invention.

Claims (7)

An inkjet ink for forming an organic semiconductor thin film, which is an organic semiconductor compound represented by the general formula (1-1), an organic semiconductor compound represented by the general formula (2-1), and represented by the general formula (3-1). At least one organic semiconductor compound selected from the organic semiconductor compounds represented by the general formula (4-1), a boiling point of 180 ° C. or higher and 250 ° C. or lower, and a surface tension of 20 mN / m or higher and 38 mN /. An inkjet ink for forming an organic semiconductor thin film containing an organic solvent of m or less.

(In the formula, R ₁₁ and R ₁₂ are groups represented by either (I) or (I-II) below, but at least one is (I).
(I)
A group of the general formula (1-2) or (1-3).

(Ar ₁₁ may have an aromatic hydrocarbon group or a hetero-aromatic _{group which may have a substituent, Ar 12} may have an aromatic hydrocarbon group or a substituent which may have a substituent. groups, R 1 _'is hydrogen atom, trialkylsilyl group having an alkyl group of 1 to 4 carbon atoms, having 1 to 20 carbon atoms alkyl group, an aromatic optionally having a substituent hydrocarbon group or a heteroaromatic It is a family group.)
(I-II)
Alkyl group having 2 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkyl group having 2 to 20 carbon atoms having a halogen atom, alkoxyalkyl group having 3 to 20 carbon atoms, alkylsulfanylalkyl having 3 to 20 carbon atoms Group, alkylaminoalkyl group with 3 to 20 carbon atoms, aromatic hydrocarbon group or heteroaromatic group, alkyl group with 1 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, carbon number having halogen atom An aromatic hydrocarbon group having an alkyl group of 1 to 20, an alkoxyalkyl group having 3 to 20 carbon atoms, an alkylsulfanyl alkyl group having 3 to 20 carbon atoms, or an alkylaminoalkyl group having 3 to 20 carbon atoms as a substituent or It is a group selected from complex aromatic groups. )

(In the formula, R ₂₁ is a group of any of (II-I) and R ₂₂ is a group selected from any of the groups of (II-II).
(II-I)
A group of the general formula (2-2) or (2-3).

(Ar ₂₁ is an aromatic hydrocarbon group or a heteroaromatic group having an alkyl group having 2 to 18 carbon atoms as a substituent, and the aromatic hydrocarbon group or the heteroaromatic group has a monocyclic or ring number. is a polycyclic 2 or 3 groups, Ar ₂₂ is an aromatic be substituted hydrocarbon group or an optionally substituted heteroaromatic group, R 2 _'is a hydrogen atom, the number of carbon atoms It is an aromatic hydrocarbon group or a heteroaromatic group which may have 1 to 20 alkyl groups and substituents.)

(II-II)
It is a group selected from a hydrogen atom, a methyl group, a cyano group, a fluoro group, and a trifluoromethyl group. )

(In the formula, R _{301 to} R ₃₁₂ are hydrogen atoms or arbitrary substituents, R ₃₀₁ and R ₃₁₂ are the same or different, R ₃₀₂ and R ₃₁₁ are the same or different, and R ₃₀₃ and R ₃₁₀ are the same. Or different, R ₃₀₄ and R ₃₀₉ are the same or different, R ₃₀₅ and R ₃₀₈ are the same or different, R ₃₀₆ and R ₃₀₇ are the same or different, but R ₃₀₁ and R ₃₁₂ , R ₃₀₂ and R ₃₁₁ and R ₃₀₃ and R. _{Of the six combinations of 310} , R ₃₀₄ and R ₃₀₉ , R ₃₀₅ and R ₃₀₈ , and R ₃₀₆ and R ₃₀₇ , at least one combination is different from each other.)

(In the formula, R ₄₂ represents a linear alkyl group having 2 to 20 carbon atoms, and R ₄₇ represents a hydrogen atom or a methyl group.) The inkjet ink for forming an organic semiconductor thin film according to claim 1, wherein the organic solvent is an organic solvent having an aromatic ring. The inkjet ink for forming an organic semiconductor thin film according to claim 1 or 2, further comprising an insulating material. The inkjet ink for forming an organic semiconductor thin film according to claim 3, wherein the insulating material is a polymer material. An organic semiconductor device including an organic semiconductor thin film obtained by using the inkjet ink for forming an organic semiconductor thin film according to any one of claims 1 to 4. A thin film transistor comprising an organic semiconductor thin film formed by using the inkjet ink for forming an organic semiconductor thin film according to any one of claims 1 to 4. An electronic device including at least one organic semiconductor device according to claim 5 and a thin film transistor according to claim 6, which is selected from the organic semiconductor device according to claim 5 and the thin film transistor according to claim 6.

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