JP6897083B2 - Organic compounds and semiconductor materials containing them - Google Patents

Description

The present invention relates to organic compounds and semiconductor materials containing them.

Transistors using amorphous silicon or polycrystalline silicon as a semiconductor material are widely used as switching elements in liquid crystal display devices and organic EL display devices. However, since these transistors using silicon have a high-temperature heat treatment process in their manufacture, they cannot be developed in the next-generation flexible display device that uses a plastic substrate due to the problem of heat resistance. In order to solve these problems, an organic transistor has been proposed in which an organic compound is used as a semiconductor material (hereinafter, a semiconductor material using an organic compound is sometimes referred to as an organic semiconductor material) instead of silicon. There is.

Organic semiconductor materials are plastics with poor heat resistance because they can be formed into ink at a low temperature by a coating method or a printing method (hereinafter, the coating method, the printing method, etc. may be referred to as a wet film forming method). It can be applied to substrates, and is expected to be applied to flexible display devices, and further to flexible electronic devices (for example, lightweight and flexible electronic tags and sensors). On the other hand, organic semiconductors initially have lower mobility (one of the indexes showing semiconductor characteristics, the unit is cm ² / Vs) as compared with silicon semiconductors, and as a result, the transistor response speed is inferior and practical. There was a problem that it was difficult to convert. However, in response to this problem, in recent years, organic semiconductor materials that give mobility that surpasses that of amorphous silicon have been developed. Among them, recently, the chrysene ([4] phenacene) skeleton is a unit that gives high mobility. It is attracting attention as.

For example, Patent Document 1 describes a compound having a 2,8-diphenylchrysene skeleton, and describes that the mobility of a transistor using this compound ^{reaches 2.8 cm 2} / Vs (). The semiconductor layer is formed by the vacuum film formation method instead of the wet film formation method.) As described above, the 2,8-diphenylcrycene derivative has a high potential from the viewpoint of having high semiconductor properties, but on the other hand, the compound described in Patent Document 1 has a problem of low solubility in a solvent. (If the solubility in a solvent is low, it is difficult to use it in a wet film forming method).
Patent Document 2 describes compounds having a 2-alkyl-8-arylchrycene skeleton, and the mobility of a transistor using these compounds can ^{reach 2.7 to 3.0 cm 2} / Vs. Described (a semiconductor layer is formed by a single crystal produced by a casting method or a vacuum film forming method). On the other hand, the mobility of a transistor having a thin film of the compound produced by a spin coating method, which is a wet film forming method, as a semiconductor layer is described as being on the order ^{of 10 -4} cm ^{2 / Vs.} As described above, since the compound described in Patent Document 2 has low solubility in a solvent, it is a problem that its characteristics are significantly deteriorated when it is subjected to a wet film forming method.
Patent Document 1 describes compounds having a 2,8-bis (m-alkylphenyl) chrysen skeleton, and the mobility of a transistor using these compounds can ^{reach 11.9 cm 2} / Vs. Described (a semiconductor layer is formed from a single crystal produced by the casting method). On the other hand, the compound described in Non-Patent Document 1 has a problem of low solubility in a solvent.
Patent Document 3 describes compounds having a 2-alkylchrysene or 2,8-dialkylchrysene skeleton, and describes that the mobility of a transistor using these compounds ^{reaches 1.1 cm 2} / Vs. (Semiconductor layer is formed by spin coating method).
However, although 2-alkylchrysene or 2,8-dialkylchrysene derivatives have both high semiconductor properties and wet film-forming properties, on the other hand, there is a problem that the crystal state of the film is changed by heat and the mobility is lowered. It has become.

Patent Document 4 discloses a compound represented by a general formula of "side chain-aromatic unit-acetylene bond-aromatic unit", but does not describe a compound according to the present invention.

Bulletin of the Chemical Society of Japan, 2015, Vol. 88, No. 9, p. 1347 Japanese Unexamined Patent Publication No. 2013-152961 JP 2015-95530 International Publication No. 2010-024139 International Publication No. 2015-137304

As described above, the feature of the organic semiconductor material is that a semiconductor element such as a transistor can be provided by a wet film forming method, and high solubility is required for that purpose. Further, in practical use, the heat resistance of the transistor is also required. Therefore, an object of the present invention is to provide a semiconductor material that provides a semiconductor element that exhibits high mobility by a wet film forming method and whose mobility does not decrease due to heat, and further, an organic substance that provides the semiconductor material. The purpose is to provide a compound.

In order to solve the above problems, the inventors have made extensive studies to obtain a semiconductor device in which a chrysene derivative having a substituent having a specific structure exhibits high mobility by a wet film forming method and the mobility does not decrease due to heat. It was found to give, and the present invention was completed.

That is, the present invention is composed of the following items.
1. 1. A compound represented by the general formula (1).

(In the formula, Ar represents an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent, and R ¹ is an acyclic alkyl having 1 to 20 carbon atoms. A group (-CH _2- in the alkyl group is -O-, -R'C = CR'-, -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'- or -C≡C- may be substituted with a hydrogen atom in the alkyl group, a halogeno group, a nitrile It may be substituted with a group or an aromatic group (where R'represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms).)
2. The Ar is represented by the general formula (2) or the general formula (3). The compound described in.

(In the formula, X ^{21 to} X ²⁵ represent a hydrogen atom or an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.)

(In the formula, X ^{31 to} X ³³ represent a hydrogen atom or an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.)
3.1. Or 2. A semiconductor material containing the compound described in 1.
4.1. Or 2. An ink containing the compound described in 1.
5.1. Or 2. A semiconductor film containing the compound described in 1.
6.1. Or 2. A semiconductor device having a semiconductor layer containing the compound described in 1.
7.1. Or 2. A transistor having a semiconductor layer containing the compound described in 1.

The organic compound of the present invention can provide a semiconductor device that exhibits high mobility by a wet film forming method and whose characteristics are not deteriorated by heat.

It is a conceptual cross-sectional view of a bottom gate bottom contact (BGBC) type transistor.

(Organic compound of the present invention)
Hereinafter, the compound of the present invention will be described.
The organic compound of the present invention is a chrysene derivative represented by the general formula (1).

(In the formula, Ar represents an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent, and R ¹ is an acyclic alkyl having 1 to 20 carbon atoms. A group (-CH _2- in the alkyl group is -O-, -R'C = CR'-, -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'- or -C≡C- may be substituted with a hydrogen atom in the alkyl group, a halogeno group, a nitrile It may be substituted with a group or an aromatic group (where R'represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms).)

Ar of the compound represented by the general formula (1) will be described.
Ar is not 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, and is not particularly limited.
A phenyl group having a phenyl group and a substituent, a naphthyl group having a naphthyl group and a substituent, an azulenyl group having an azulenyl group and a substituent, an anthranel group having an anthrasenyl group and a substituent, a phenanthryl group having a phenanthryl group and a substituent, Acenaphthylenyl group having an acenaphthylenyl group and a substituent, an acenaphthenyl group having an acenaphthenyl group and a substituent, a fluorenyl group having a fluorenyl group and a substituent, a naphthacenyl group having a naphthacenyl group and a substituent, a pyrenyl group having a pyrenyl group and a substituent, Derived from p-terphenyl, a chrysenyl group having a chrysenyl group and a substituent, a perylenyl group having a perylenyl group and a substituent, a monovalent group derived from biphenyl and a monovalent group derived from biphenyl having a substituent. Monovalent groups derived from p-terphenyl having a monovalent group and a substituent, monovalent groups derived from p-quarterphenyl and monovalent groups derived from p-quarterphenyl having a substituent and the like. Ring or polycyclic aromatic hydrocarbon groups;

Pyrrolyl groups with pyrrolyl groups and substituents, imidazolyl groups with imidazolyl groups and substituents, pyrazolyl groups with pyrazolyl groups and substituents, triazolyl groups with triazolyl groups and substituents, tetrazolyl groups with tetrazolyl groups and substituents,
A frill group having a frill group and a substituent, a thienyl group having a thienyl group and a substituent,
Oxazolyl group having oxazolyl group and substituent, thiazolyl group having thiazolyl group and substituent, oxadiazolyl group having oxadiazolyl group and substituent, thiadiazolyl group having thiadiazolyl group and substituent,

Pyrorothiazolyl group having a pyrorothiazolyl group and a substituent, a thienothienyl group having a thienothienyl group and a substituent,
Indolyl group with indolyl group and substituent, indolinyl group with indolinyl group and substituent, indridinyl group with indridinyl group and substituent, pyrrolopyridadinyl group with pyrolopyridadinyl group and substituent, benzotoria Bentotriazolyl group with zolyl group and substituent, benzofuryl group with benzofuryl group and substituent, benzothienyl group with benzothienyl group and substituent, benzoxazolyl with benzoxazolyl group and substituent Group,

Carbazolyl group with carbazolyl group and substituent, monovalent group derived from dibenzofuran and monovalent group derived from dibenzofuran with substituent, derived from dibenzothiophene with monovalent group and substituent derived from dibenzothiophene Is a monovalent group,
Pyridyl group with pyridyl group and substituent, pyridadinyl group with pyridadinyl group and substituent, pyrimidinyl group with pyrimidinyl group and substituent, pyrazinyl group with pyrazinyl group and substituent,

A quinolinyl group having a quinolinyl group and a substituent, an isoquinolinyl group having an isoquinolinyl group and a substituent, a benzoquinolinyl group having a benzoquinolinyl group and a substituent,
A monovalent group derived from bithiophene and a monovalent group derived from bithiophene having a substituent, a monovalent group derived from tarthiophene and a monovalent group derived from tarthiophene having a substituent, derived from quarterthiophene A monocyclic or polycyclic heteroaromatic group such as a monovalent group derived from a quarterthiophene having a monovalent group and a substituent.
And so on.

The Ar substituent is not particularly limited as long as it is a substituent known and commonly used as a substituent of an aromatic compound, and is, for example,
Hydrogen atom, halogeno group, nitro group, nitrile group,
Acyclic or cyclic alkyl groups with 1 to 20 carbon atoms (-CH ₂ − in the alkyl groups are -O-, -R so that oxygen, sulfur and nitrogen atoms are not directly bonded to each other. 'C = CR' -, - CO - , - OCO -, - COO -, - S -, - SO 2 -, - SO -, - NH -, - NR'- or -C≡C- substituted with Often, the hydrogen atom in the alkyl group may be substituted with a halogeno group, a nitrile group or an aromatic group (where R'is an acyclic or cyclic alkyl group having 1 to 20 carbon atoms. Represents.).),
An aromatic group (the aromatic group may be substituted with a halogeno group, a nitro group, a nitrile group, an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, an aromatic group, and the alkyl group. -CH _2- inside, -O-, -CR "= CR"-, -CO-, -OCO-, -COO-, so that oxygen atom, sulfur atom and nitrogen atom are not directly bonded to each other. _{-S -, - SO 2 -,} - SO -, - NH -, - NR''- or -C≡C- may be substituted with a hydrogen atom in the alkyl group, a halogeno group, a nitrile group or an aromatic It may be substituted with a group group (wherein R ″ represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms).
And so on.

As Ar, the group represented by the general formula (2) or (3) is preferable from the viewpoint of expressing high mobility among the aromatic groups.

(In the formula, X ^{21 to} X ²⁵ represent a hydrogen atom or an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.)

(In the formula, X ^{31 to} X ³³ represent a hydrogen atom or an acyclic or cyclic alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.)
The group represented by the general formula (4) or (5) is more preferable.

(In the formula, X ⁴¹ , X ⁴² , X ⁴⁴ , X ⁴⁵ represent a hydrogen atom, X ⁴³ represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms, and * represents a monovalent substituent. Represents a bond.)

(In the formula, X ⁵² and X ⁵³ represent a hydrogen atom, X ⁵¹ represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.)

^{Next, R 1 of the} compound represented by the general formula (1) will be described.
R ¹ is an acyclic alkyl group having 1 to 20 carbon atoms (-CH _2- in the alkyl group is -O-, -R so that oxygen atom, sulfur atom and nitrogen atom are not directly bonded to each other. ´C = CR ′-, −CO−, −OCO−, −COO−, −S−, −SO2-, −SO−, −NH−, −NR′− or −C≡C− may be substituted. , The hydrogen atom in the alkyl group may be substituted with a halogeno group, a nitrile group or an aromatic group (where R'represents an acyclic or cyclic alkyl group having 1 to 20 carbon atoms. .).).

Specifically, -O-,-so that the acyclic alkyl group having 1 to 20 carbon atoms (-CH _2- in the alkyl group does not directly bond with the oxygen atom, the sulfur atom and the nitrogen atom, respectively). R'C = CR '-, - CO -, - OCO -, - COO -, - S -, - SO 2 -, - SO -, - NH -, - NR'- or C≡C- substituted with Often, the hydrogen atom in the alkyl group may be substituted with an aromatic group, a halogeno group, or a nitrile group (where R'is an acyclic or cyclic alkyl group having 1 to 20 carbon atoms. (Represented).) Are (A-1) a linear or branched alkyl group having 1 to 20 carbon atoms, (A-2) an alkoxy group having 1 to 19 carbon atoms, and (A-3) 2 carbon atoms. ~ 19 alkoxyalkyl groups, (A-4) alkenyl groups with 2 to 20 carbon atoms, (A-5) alkanoyl groups with 2 to 20 carbon atoms, (A-6) alkanoyls with 3 to 20 carbon atoms Alkyl group, (A-7) alkoxycarbonyl group with 2 to 20 carbon atoms, (A-8) alkanoyloxy group with 2 to 20 carbon atoms, (A-9) alkylsulfanyl group with 1 to 19 carbon atoms , (A-10) Alkyl sulfanyl alkyl group having 2 to 19 carbon atoms, (A-11) Alkyl sulfonyl group having 1 to 19 carbon atoms, (A-12) Alkyl sulfonyl alkyl group having 2 to 19 carbon atoms. , (A-13) Alkyl sulfinyl group having 1 to 19 carbon atoms, (A-14) Alkyl sulfinyl alkyl group having 2 to 19 carbon atoms, (A-15) Alkyl amino group having 1 to 19 carbon atoms, (A-16) is an alkylaminoalkyl group having 2 to 19 carbon atoms, and (A-17) is an alkynyl group having 2 to 20 carbon atoms.

Among the above (A-1) to (A-17), from the viewpoint of improving the film-forming property and mobility of the compound of the present invention, (A-1) linear or branched having 1 to 20 carbon atoms. Alkyl groups, (A-2) alkoxy groups with 1 to 19 carbon atoms, (A-3) alkoxyalkyl groups with 2 to 19 carbon atoms, (A-4) alkenyl groups with 2 to 20 carbon atoms, (A-4). A-9) an alkylsulfanyl group having 1 to 19 carbon atoms, (A-10) an alkylsulfanyl alkyl group having 2 to 19 carbon atoms, or (A-17) an alkynyl group having 2 to 20 carbon atoms is preferable.
In order to obtain a compound having a higher mobility, (A-1) a linear alkyl group having 1 to 20 carbon atoms is more preferable.

Specific examples of (A-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;
And so on.

Regarding the compound represented by the general formula (1), the compound represented by the general formula (6) or (7) is preferable from the viewpoint of improving the mobility.

(R ⁶¹ represents a linear alkyl group having 1 to 20 carbon atoms, and R ⁶² represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms.)

(R ⁷¹ represents a linear alkyl group having 1 to 20 carbon atoms, and R ⁷² represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms.)

Specific examples of the compound of the present invention include the following compounds, but the compound of the present invention is not limited thereto.

(Method for producing the compound of the present invention)
The method for producing the compound of the present invention will be described.
The method for producing the compound of the present invention is not particularly limited as long as it is a method capable of obtaining the compound of the present invention. As shown below, the compound of the present invention can be produced by combining known and conventional synthetic reactions.

The method for producing the compound of the present invention will be described using the production scheme (S1) formula.

^(Wherein, R 1, Ar has the same meaning as ^R 1, Ar in formula (1).)

First, 2,8-dimethoxy-5,6,11,12-tetrahydrochrysene is dehydrogenated by allowing palladium / carbon to act (first step), and then demethylated with boron tribromide (second step). ). Then, by the action of trifluoromethanesulfonic anhydride bis (trifluoromethanesulfonyl) is of (third stage), a Grignard reagent (R ¹ -MgBr) and allowed to cross-coupling reaction after accordingly, alkylated (4 stages Eye). Finally, the Sonogashira coupling reaction with aryl acetylene is carried out to obtain the desired compound (fifth step).

(Semiconductor material of the present invention)
The semiconductor material of the present invention will be described.
The compound of the present invention can be used as a semiconductor material for semiconductor devices. The form of the semiconductor material of the present invention is not particularly limited as long as it can be used for manufacturing a semiconductor device, and is a single crystal, a polycrystalline, a powder, an amorphous film, a polycrystalline film, a single crystal film, or a thin film. Solid forms such as; liquid forms such as solutions, dispersions, coatings, inks; and the like. Above all, considering that the characteristic of the organic semiconductor material is that a semiconductor element can be provided by a wet film forming method, a coating liquid or an ink is preferable.
The semiconductor material of the present invention may contain a material other than the compound of the present invention as long as the provided semiconductor element exhibits desired semiconductor characteristics.

(Ink of the present invention)
The ink of the present invention will be described.
The ink of the present invention is a material for forming a semiconductor film containing the compound of the present invention by a wet film forming method, and further is a semiconductor layer containing the compound of the present invention of the present invention. It is a material for forming a semiconductor layer of a semiconductor element by a wet film forming method, and by extension, a material for giving the semiconductor element of the present invention by a wet film forming method.

In addition to the compound of the present invention, the ink of the present invention contains a solvent capable of dissolving or dispersing the compound of the present invention.
Such a solvent is not particularly limited as long as it can dissolve or disperse the compound of the present invention, for example.
Ester solvents such as ethyl acetate, normal propyl acetate, isopropyl acetate, propylene glycol monomethyl ether acetate (PGMAc), 3-methoxy-3-methyl-butyl acetate, ethoxyethyl propionate (EEP), propylene carbonate;

Methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-butanol, 3-methoxy-3-methyl-1-butanol, 1,3-butanediol, 1-pentanol, 4- Alcohol-based solvents such as methyl-2-pentanol, 1-hexanol, cyclohexanol, and industrial higher alcohols (for example, Diador series (trade name, manufactured by Mitsubishi Chemical));

Hydrocarbon solvents such as pentane, n-hexane, hexane, cyclohexane, methylcyclohexane, n-octane, n-decane, toluene and xylene;
Chlorine-based solvents such as dichloromethane and chloroform;

Benzene, toluene, cumene, n-propylbenzene, n-butylbenzene, n-pentylbenzene, o-xylene, m-xylene, p-xylene, p-simene, 1,4-diethylbenzene, mecitylene, 1,3,5 -Triethylbenzene, anisole, 2-methylanisole, 3-methylanisole, 4-methylanisole, 2,5-dimethylanisole, 1,3-dimethoxybenzene, 3,5-dimethoxytoluene, 2,4-dimethylanisole, phenitol , Methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, chlorobenzene, o-dichlorobenzene, trichlorobenzene, tetralin, 1,5-dimethyltetraline, 1-methylnaphthalene, industrial aromatic solvents (eg, for example. Aromatic solvents such as benzene 100, benzene 150, etc. (trade name, manufactured by Exxon Mobile);

Tetrahydrofuran, 2-methyltetraethanol, dioxane, ethylene glycol diethyl ether (monoglyme), diglime, triglime, ethylene glycol monomethyl ether (cellosolve), ethyl cellosolve, propiocellosolve, butyrocellosolve, phenylcellosolve, diethylene glycol methyl ether, diethylene glycol ethyl ether , Diethylene glycol propyl ether, diethylene glycol butyl ether, benzyl ethyl ether, ethyl phenyl ether, diphenyl ether, methyl-t-butyl ether, cyclopentyl methyl ether, cyclohexyl methyl ether benzonitril propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether. , Ethylene glycol tertiary butyl ether, dipropylene glycol monomethyl ether, ethylene glycol butyl ether, ethylene glycol ethyl ether, ethylene glycol methyl ether, diethylene glycol butyl ether, diethylene glycol ethyl ether and other ether-based solvents;

Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, 2-hexanone, 2-heptanone, 3-heptanone, acetophenone, propiophenone, butyrophenone, cyclohexanone;

Aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide, diethylformamide, N-methyl-2-pyrrolidone;
And so on.
The solvent used in the ink of the present invention may be one kind or two or more kinds.

The ink of the present invention may contain a semiconductor material other than the compound of the present invention as another component, depending on the intended use. Examples of such a semiconductor material include an electron donating material, an electron accepting material, an electron transporting material, a hole transporting material, a light emitting material, and a light absorbing material.

Further, the ink of the present invention may contain a polymer compound, a resin, a constitutional component, a surfactant, a mold release agent and the like as other components. These components are added as necessary to impart printability and film-forming property (film-forming ability) to the ink of the present invention.

The resin that can be contained in the ink of the present invention is not particularly limited as long as it is a known and commonly used insulating resin, and for example,
Cyanoethyl pullulan, cellulose acetate propionate (CAP), cellulose triacetate (TAC), polyalilate (PAR), polyimide, polyester, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetherimide (PEI), polyether Etherketone (PEEK), Polyethersulfone (PES), Polyvinylidene Chloride (PVDC), Polyvinyl Chloride (PVC), Polycarbonate (PC), Polycycloolefin, Polystyrene and Polystyrene Derivatives, Polytetrafluoroethylene (PTFE), Poly Paraxylylene derivatives (eg, parylene series (trade name)), polyvinyl alcohol (PVA), polyvinylphenol (PVP), polyphenylene sulfide (PPS), polymethylmethacrylate (PMMA), acrylic resins, amorphous fluororesins (eg, sai) Top series (trade name, manufactured by Asahi Glass), alkyd resin, urethane resin, epoxy resin, electron beam curable resin (for example, electron beam curable acrylic resin and electron beam curable metal acrylic resin), phenoxy resin, phenol Examples of polymer compounds such as resins, fluororesins, unsaturated polyester resins, polyimide resins, polyvinylphenol resins, melamine resins, and UV curable resins (for example, UV curable acrylic resins and UV curable metaacrylic resins) are mentioned. Can be done.
The resin contained in the ink of the present invention may be one kind or two or more kinds.
The concentration of the resin in the ink is not particularly limited as long as the semiconductor element using the ink of the present invention exhibits desired semiconductor characteristics, and is usually in the range of 1 to 10% by mass. It is preferably in the range of 3 to 7% by mass, and more preferably in the range of 3 to 7% by mass.

The constitutional component that can be contained in the ink of the present invention is not particularly limited as long as it is a known and commonly used electrically insulating inorganic fine particle and a known and commonly used electrically insulating pigment.
Aerosil series (trade name, made by Evonik),
Silocia, Silohobic, Siloput, Silopage, SiloPure, SiloSfair, Silomask, Sylwell, Fuji Balloon (above, trade name, made by Fuji Silysia),
PMA-ST, IPA-ST (above, product name, manufactured by Nissan Chemical Industries, Ltd.),
Inorganic fine particles such as NANOBIC3600 series and NANOBIC3800 series (above, trade name, manufactured by Big Chemie);
Pigments such as EXCEDIC BLUE0565, EXCEDIC RED0759, EXCEDIC YELLOW 0599, EXCEDIC GREEN0358, EXCEDIC YELLOW0648 (above, trade name DIC);
And so on.
The constitutional component contained in the ink of the present invention may be one kind or two or more kinds.
The concentration of the constitutional component in the ink is not particularly limited as long as the semiconductor element using the ink of the present invention exhibits desired semiconductor characteristics, and is usually 0 to 20% by mass of the active ingredient. It is preferably in the range of.

The surfactant that can be contained in the ink of the present invention is not particularly limited as long as it is a known and commonly used electrically insulating surfactant, and for example,
Examples thereof include hydrocarbon-based surfactants, silicone-based surfactants, and fluorine-based surfactants. Among them, fluorine-based surfactants having a linear perfluoroalkyl group having a chain length of C6 or more (for example, Megafvck F-482, Megafvck F-470 (R-08), Megafvck F-472SF, Mega). Fvck R-30, Mega Fvck F-484, Mega Fvck F-486, Mega Fvck F-172D, Mega Fvck F178RM (above, trade name, manufactured by DIC)) are preferable.
The surfactant contained in the ink of the present invention may be one kind or two or more kinds.
The concentration of the surfactant in the ink is not particularly limited as long as the semiconductor device using the ink of the present invention exhibits desired semiconductor characteristics, and is usually 0.01 to 0.01 to 0.01 for the active ingredient. It is preferably in the range of 5.00% by mass, and more preferably in the range of 0.05 to 1.00% by mass of the active ingredient.

The release agent that can be contained in the ink of the present invention is not particularly limited as long as it is a known and commonly used electrically insulating silicone-based compound, and is, for example, dimethyl silicone oil, dimethyl silicone rubber, silicone resin, or organic. Examples thereof include modified silicone oil, methylphenyl silicone oil, long-chain alkyl modified silicone oil, a mixture of a fluorine compound and a silicone polymer, and fluorine-modified silicone. Of these, the Granol series (trade name, manufactured by Kyoei Co., Ltd.) and the KF-96L series (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) are preferable from the viewpoint of mold releasability and compatibility with the resin.
The release agent contained in the ink of the present invention may be one kind or two or more kinds.
Further, the concentration of the release agent in the ink is not particularly limited as long as the semiconductor element using the ink of the present invention exhibits desired semiconductor characteristics, and is usually 0. It is preferably in the range of 0 to 5.0% by mass, and more preferably in the range of 0.0 to 3.0% by mass of the active ingredient.

In addition, the ink of the present invention may contain a leveling agent, a dispersant, an antifoaming agent and the like as arbitrary components in a timely manner.

The concentration of the compound of the present invention in the ink is not particularly limited as long as the semiconductor device using the ink of the present invention exhibits desired semiconductor characteristics, and is usually 0.01 to 20.00. It is preferably in the range of% by mass, more preferably in the range of 0.05 to 10.00% by mass, and even more preferably in the range of 0.10 to 10.00% by mass.

(Semiconductor device of the present invention)
The semiconductor device of the present invention will be described.
The semiconductor device of the present invention is not particularly limited as long as it is a semiconductor device having a semiconductor layer made of the compound of the present invention. Conversion elements; field effect transistors, electrostatic induction transistors, bipolar transistors, thin film transistors, etc .; organic EL devices, light emitting transistors, and other light emitting elements; memory; temperature sensors, chemical sensors, gas sensors, humidity sensors, radiation sensors, biotechnology Sensors such as sensors, blood sensors, immune sensors, artificial retinas, taste sensors, and pressure sensors; logic circuit units such as inverters, ring oscillators, and RFIDs; and the like can be mentioned.

(Transistor of the present invention)
The transistor of the present invention will be described.
A transistor is a semiconductor element having a gate electrode, a gate insulating layer, a source electrode, a drain electrode, and a semiconductor layer as essential elements, and is classified into various structures depending on how each electrode and each layer are arranged.

The structure of the transistor of the present invention is not particularly limited as long as it contains the compound of the present invention as a semiconductor layer. For example, a bottom gate bottom contact (hereinafter abbreviated as BGBC) type transistor and a bottom gate top contact (hereinafter abbreviated as BGBC) Hereinafter, BGTC type transistor, top gate bottom contact (hereinafter, abbreviated as TGBC) type transistor, top gate top contact (hereinafter, abbreviated as TGTC) type transistor, metal-based organic transistor (hereinafter, abbreviated as MBOT) type transistor. ), Static induction transistor (hereinafter abbreviated as SIT) and the like.

Next, the substrate which is a component of the transistor of the present invention will be described.
The substrate material is not particularly limited as long as it can be processed into a plate shape, a sheet shape, a film shape, or the like.
silicon;
Inorganic glass such as quartz glass, soda glass, borosilicate glass, non-alkali glass;
Cellulose acetate propionate (CAP), cellulose triacetate (TAC), polyarylate (PAR), polyimide, polyethylene (PE), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetherimide (PEI), polyether Resins and polymer compounds such as ether ketone (PEEK), polyethersulfone (PES), polypropylene (PP), polycarbonate (PC), polycycloolefin, polyphenylene sulfide (PPS), polymethylmethacrylate (PMMA);
And so on.

Among them, an inorganic substrate such as a glass plate or a silicon wafer is preferable from the viewpoint of improving the productivity of the transistor, and a glass sheet, a resin sheet, a plastic film or the like is preferable from the viewpoint of obtaining a flexible transistor. Preferably, in addition to flexibility, a resin sheet or a plastic film is more preferable from the viewpoint of weight reduction, portability and impact resistance.

Next, an electrode which is a component of the transistor of the present invention will be described.
The material of the gate electrode, the source electrode, and the drain electrode is not particularly limited as long as it is a conductive material, and examples thereof include an inorganic conductive material and an organic conductive material.

Examples of inorganic conductive materials include lithium, beryllium, carbon, sodium, magnesium, aluminum, silicon, potassium, calcium, scandium, titanium, chromium, manganese, iron, nickel, copper, zinc, gallium, zirconium, niobium, and so on. Molybdenum, silver, tin, antimony, hafnium, tungsten, platinum, gold, graphite, glassy carbon, tin oxide, tin-doped indium oxide (ITO), fluorine-doped zinc oxide, sodium-potassium alloy, molybdenum-tantal alloy, aluminum-aluminum oxide. Mixture, silver-silver oxide mixture, magnesium-aluminum mixture, magnesium-indium mixture, magnesium-silver mixture, magnesium-copper mixture, lithium-aluminum mixture, dope silicon, carbon paste, silver ink, silver paste, copper ink, copper paste , Nano silver, nano copper and the like.
On the other hand, examples of the organic conductive material include conductive polyaniline, conductive polyaniline derivative, conductive polypyrrole, conductive polypyrrole derivative, conductive polythiophene, conductive polythiophene derivative, and a complex of polyethylene dioxythiophene and polystyrene sulfonic acid ( Known and commonly used conductive polymers whose electrical conductivity has been improved by doping with PEDOT-PSS) or the like;
Charge transfer complexes such as the tetrathiafulvalene-tetracyanoquinodimethane complex;
And so on.

In addition, each electrode may be made of one kind of conductive material, or may be made of two or more kinds of conductive materials. When two or more types are used, they may be mixed or laminated. Further, the same conductive material may be used in the gate electrode, the source electrode and the drain electrode, and different conductive materials may be used in each electrode.

The thickness of the electrode is appropriately determined within a range in which the desired electrical conductivity can be achieved, depending on the type of the conductive material used to form the electrode, and is usually in the range of 1 nm to 1 μm. It is preferably in the range of 10 nm to 200 nm, more preferably in the range of 20 nm to 100 nm.

The shapes of the source electrode and the drain electrode are not particularly limited as long as they are formed so as to oppose each other with a substantially constant interval (this interval corresponds to the channel length (L)).

The channel length (L) is usually preferably in the range of 0.1 μm to 1 mm, more preferably in the range of 0.5 μm to 200 μm, and further preferably in the range of 1 μm to 100 μm.

As a method for forming the electrode, a known and commonly used method as described in "Basics of Materials Science No. 6 Basics of Organic Transistors (Aldrich)" can be mentioned, and a desired shape (pattern) and a desired shape can be mentioned. The method is not particularly limited as long as it can form an electrode having a thickness, for example.
First, a conductive film is once formed in a wide range (once the conductive film is solid (entire surface)) by using a wet film forming method or a dry film forming method, and then a resist is applied on the "solid conductive film". Is patterned by photolithography or printing, and then etched;
A method of patterning the "solid conductive film" by laser ablation or the like;
A method of directly patterning by a dry film formation method using a mask;
A method of directly patterning using the printing method;
And so on.

Examples of the dry film deposition method include chemical vapor deposition (CVD) methods such as plasma CVD method, thermal CVD method, and laser CVD method; physical vapor deposition (PVD) method such as vacuum vapor deposition method, sputtering method, and ion plating method; ,
Examples of the wet film forming method include an electrolytic plating method, a dip plating method, an electroless plating method, a sol-gel method, an organic metal decomposition (MOD) method, a coating method, a printing method and the like.
The method via the mask includes a metal mask method and a lift-off method, and the coating method includes an ESD (Electro Spray Deposition) method, an ESDUS (Evaporative Spray Deposition Method from Ultra-dilute Solution) method. Method, air knife coating method, edge casting method, impregnation coating method, kiss coating method, cast coating method, squeeze coating method, spin coating method, slit coating method, electrostatic coating method, electrostatic spray coating method, die coating method, ultrasonic spray Coat method, supercritical spray coat method, dispense method, etc., dip coat method, doctor blade coat method, transfer roll coat method, drop cast method, bar coat method, blade coat method, reverse coat method, roll coat method, wire bar coat Law, etc.
The printing methods include an inkjet printing method, an offset printing method, a capillary pen printing method, a gravure printing method, a gravure offset printing method, a screen printing method, a dispense method, a letterpress printing method, a letterpress reversal printing method, a drop cast method, and flexo printing. Examples include the method, the flat plate printing method, and the microcontact printing method.

Above all, from the viewpoint of reducing the manufacturing cost, a method using a wet film forming method that does not require a vacuum environment is preferable, and among the wet film forming methods, a method using a printing method with a small number of steps is more preferable.

Next, the gate insulating layer, which is a component of the transistor of the present invention, will be described.
The gate insulating layer has a function of electrically insulating the gate electrode and the source electrode, the gate electrode and the drain electrode, and the gate electrode and the semiconductor layer. Therefore, the material of the gate insulating layer is not particularly limited as long as it is an electrically insulating material, and for example, cyanoethyl pullulan, cellulose acetate propionate (CAP), cellulose triacetate (TAC), and polyarylate (PAR). ), Polyimide, Polyester, Polyethylene terephthalate (PET), Polyethylene naphthalate (PEN), Polyetherimide (PEI), Polyether ether ketone (PEEK), Polyether sulfone (PES), Polyvinylidene chloride (PVDC), Polychloride Vinyl (PVC), Polycarbonate (PC), Polycycloolefin, Polystyrene and Polystyrene Derivatives, Polytetrafluoroethylene (PTFE), Polyparaxylylene Derivatives (eg Parylene Series ™), Polyvinyl Alcohol (PVA), Polyvinyl Phenol (PVP), polyphenylene sulfide (PPS), polymethylmethacrylate (PMMA), acrylic resin, amorphous fluororesin (for example, Cytop series (trade name, manufactured by Asahi Glass)), alkyd resin, urethane resin, epoxy resin, electron beam Curable resin (for example, electron beam curable acrylic resin or electron beam curable methacrylic resin), phenol resin, polyimide resin, polyvinyl phenol resin, phenoxy resin, phenol resin, fluororesin, unsaturated polyester resin, melamine resin, Polymer compounds such as UV curable resins (eg, UV curable acrylic resins and UV curable methacrylic resins);
Inorganic substances such as Al ₂ O ₃ , SiO ₂ , Ba _x Sr _(1-x) TiO ₃ , BaTi _x Zr _(1-x) O _3;
And so on.

The gate insulating layer may be made of one kind of insulating material or may be made of two or more kinds of insulating materials. It may also contain a reaction (polymerization) initiator, a cross-linking agent, a cross-linking aid, and the like.
When composed of two or more kinds of insulating materials, each insulating material may be simply mixed, or a covalent bond may be formed between the insulating materials. Further, when a reaction (polymerization) initiator, a cross-linking agent, and a cross-linking auxiliary are contained, these materials and the insulating material may be simply mixed, and a covalent bond is formed between these materials. May be good.
The thickness of the gate insulating layer is appropriately determined within a range in which the desired insulating property can be achieved, depending on the type of the insulating material used to form the gate insulating layer, and is usually 10 nm to 5 μm. It is preferably in the range of.

The method for forming the gate insulating layer is particularly limited as long as a film (layer) capable of electrically insulating between the gate electrode and the source electrode, between the gate electrode and the drain electrode, and between the gate electrode and the semiconductor layer can be formed. Instead, for example, known and commonly used dry film forming methods and wet film forming methods can be mentioned.

Examples of the dry film forming method include a chemical vapor deposition (CVD) method such as a plasma CVD method, a thermal CVD method, and a laser CVD method;
Physical vapor deposition (PVD) methods such as vacuum deposition, sputtering, ion plating, etc.
Examples of the wet film forming method include an electrolytic plating method, a dip plating method, an electroless plating method, a sol-gel method, an organic metal decomposition (MOD) method, a coating method, a printing method and the like.
As the coating method, an ESD (Electro Spray Deposition) method, an ESDUS (Evasorative Spray Deposition) method, an Ultra-dilute Solution) method, an air doctor coating method, an air knife coating method, an edge casting method, an edge casting method, an impregnation coating method, and an impregnation coating method. Coat method, squeeze coat method, spin coat method, slit coat method, electrostatic coat method, electrostatic spray coat method, die coat method, ultrasonic spray coat method, supercritical spray coat method, dispense method, etc., dip coat method, doctor Blade coat method, transfer roll coat method, drop cast method, bar coat method, blade coat method, reverse coat method, roll coat method, wire bar coat method, etc.
The printing methods include an inkjet printing method, an offset printing method, a capillary pen printing method, a gravure printing method, a gravure offset printing method, a screen printing method, a dispense method, a letterpress printing method, a letterpress reversal printing method, a drop cast method, and flexo printing. Examples include the method, the flat plate printing method, and the microcontact printing method.

Above all, from the viewpoint of reducing the manufacturing cost, a method using a wet film forming method, which does not require vacuum equipment, is preferable.
When patterning is required, it can be patterned by the same method as described in the section "Electrodes".

The semiconductor layer which is a component of the transistor of the present invention will be described.
A feature of the transistor of the present invention is that the compound of the present invention is contained in the semiconductor layer which is a component thereof. The semiconductor layer, which is a component of the transistor of the present invention, may contain a material other than the compound of the present invention as long as it can exhibit desired semiconductor characteristics. Examples of such a material include other semiconductor materials, polymer compounds and resins, constitutional components, surfactants, mold release agents and the like described in the section of "(Ink of the present invention)".

The thickness of the semiconductor layer is appropriately determined within a range in which desired semiconductor characteristics can be achieved, depending on the type of semiconductor material used to form the semiconductor layer, and is usually in the range of 0.5 nm to 1 μm. It is preferably in the range of 5 nm to 500 nm, more preferably in the range of 10 nm to 300 nm.

The method for forming the semiconductor layer is not particularly limited as long as it can form the semiconductor layer so as to cover at least the channel region (the region sandwiched between the source electrode and the drain electrode), and is not particularly limited. Examples thereof include a conventional dry film forming method and a wet film forming method.

As a dry film forming method, for example,
Chemical vapor deposition (CVD) methods such as plasma CVD method, thermal CVD method, laser CVD method, etc.;
Physical vapor deposition (PVD) methods such as vacuum deposition, sputtering, and ion plating;
As a wet film forming method, for example,
ESD (Electro Spray Deposition) method, ESDUS (Evasorative Spray Deposition) method, Air Doctor Coat Method, Air Knife Coat Method, Edge Cast Method, Impregnation Coat Method, Kiss Coat Method, Coat Method, Coat Method, Coat Method, Coat Method Coat method, slit coat method, electrostatic coat method, electrostatic spray coat method, die coat method, ultrasonic spray coat method, supercritical spray coat method, dispense method, etc., dip coat method, doctor blade coat method, transfer roll coat method , Drop casting method, bar coating method, blade coating method, reverse coating method, roll coating method, wire bar coating method, etc.
Inkjet printing method, offset printing method, capillary pen printing method, gravure printing method, gravure offset printing method, screen printing method, dispense method, letterpress printing method, letterpress reversal printing method, dropcast method, flexo printing method, flat plate printing method, Printing methods such as micro contact printing method;
And so on.

Above all, a method using a wet film forming method is preferable from the viewpoint of reducing the manufacturing cost and lowering the temperature of the manufacturing process.

Further, in forming the semiconductor layer, if necessary, annealing may be performed after the film is formed as described above for the purpose of enhancing the crystallinity of the semiconductor material and improving the semiconductor characteristics. The annealing temperature is preferably in the range of 50 to 200 ° C., more preferably in the range of 70 to 200 ° C., and the annealing time is preferably in the range of 10 minutes to 12 hours, 1 hour to 10 hours. It is more preferably in the time range, and even more preferably in the range of 30 minutes to 10 hours.

Applications of the transistor of the present invention include a switching element of pixels constituting a display device, a signal driver circuit of pixels constituting a display device, a memory circuit, a sensor circuit, an inverter, a ring oscillator, an RFID and the like.
Examples of the display device include a liquid crystal display device, a distributed liquid crystal display device, an electrophoresis display device, a particle rotation display device, an electrochromic display device, an organic EL display device, electronic paper, and the like.

The present invention will be described in more detail with reference to Examples.

(Example 1)
<Method for producing compound (101)>
A method for producing the compound (101) will be described. The compound (101) is a compound represented by the general formula (1), which corresponds to the case where ^{Ar is a phenyl group and R 1 is a hexyl group.}

The manufacturing scheme is shown in (S101).

(S101)

First, a method for synthesizing compound (101-1) will be described.
2,8-Dimethoxy-5,6,11,12-tetrahydrochrysene 11.0 g (37.5 mmol), 50%, obtained by the method described in Journal of Organic Chemistry, 1992, No. 57, p. 1262, under an argon atmosphere. 110 mL of mesitylene was added to 8.40 g of water-containing 10% -Pd / C (manufactured by N.E.Chemcat), and the mixture was stirred at 160 ° C. for 6 hours and then allowed to cool. The precipitated white solid was filtered and washed with ethyl acetate. The obtained white solid was dried to obtain 7.77 g (yield, 71.9%) of compound (101-1).
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.68-8.66 (m, 2H), δ8.64 (d, J = 8.8 Hz, 2H), δ7.93 (d, J = 8.8 Hz, 2H), δ7.38-7.35 (m, 4H), δ4.02 (s, 6H).

Next, a method for synthesizing compound (101-2) will be described.
Under an argon atmosphere, 500 mL of dehydrated dichloromethane was added to 5.70 g (19.8 mmol) of compound (101-1), and the mixture was stirred at 0 ° C. After dropping 47 mL (47 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. The mixture was heated under reflux for another 8 hours and allowed to cool to room temperature. 200 mL of water was added to the reaction solution, and the precipitated white solid was filtered to obtain 5.14 g (yield, 100%) of compound (101-2). It was subjected to the next reaction without further purification.

Next, a method for synthesizing compound (101-3) will be described.
Under an argon atmosphere, 80 mL of dehydrated dichloromethane and 14 mL (99 mmol) of triethylamine were added to 5.14 g (19.8 mmol) of compound (101-2), and the mixture was stirred at 0 ° C. After 8.3 mL (49 mmol) of trifluoromethanesulfonic anhydride was added dropwise to the reaction mixture, the temperature was raised to room temperature and the mixture was stirred for 4 hours. After stopping the reaction by adding 100 mL of dilute hydrochloric acid to the reaction solution, the aqueous layer was withdrawn, and then the organic layer was washed twice with dilute hydrochloric acid. The yellow solid obtained by concentrating the organic layer under reduced pressure was separated and purified by silica gel column chromatography (hexane / chloroform = 80/20 → 50/50) to obtain 4.45 g of compound (101-3) (yield, 43. 0%) was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.87 (d, J = 9.2 Hz, 2H), δ8.77 (d, J = 8.8 Hz, 2H), δ8.07 (d, J = 8. 8Hz, 2H), δ7.93 (d, J = 2.8Hz, 2H), δ7.64 (dd, J = 9.2Hz, J = 2.8Hz, 2H).

Next, a method for synthesizing compound (101-4) will be described.
Under an argon atmosphere, 20 mL of dehydrated tetrahydrofuran and 1 mL of N-methylpyrrolidone were added to 0.995 g (1.95 mmol) of compound (101-3) and 0.0675 g (0.185 mmol) of acetylacetone iron (III), and the mixture was stirred at 0 ° C. .. 1.8 mL (3.6 mmol) of a 2.0 M ether solution of hexylmagnesium bromide was added dropwise to the reaction mixture, and the mixture was stirred for 30 minutes. Water was added to the reaction solution to stop the reaction, and then Celite filtration was performed. The solid obtained by concentrating the filtrate is separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 60/40) to obtain 0.267 g of compound (101-4) (yield: 30.6%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.85-8.79 (m, 2H), δ8.71-8.60 (m, 2H), δ8.01-7.97 (m, 2H), δ7 .88 (d, J = 2.4Hz, 1H), δ7.79 (s, 1H), δ7.61-7.57 (m, 2H), δ2.87 (t, J = 7.6Hz, 2H) , Δ1.81-1.70 (m, 2H), δ1.46-1.27 (m, 6H), δ0.93 (t, J = 6.8Hz, 3H).

Finally, a method for synthesizing compound (101) will be described.
Under an argon atmosphere, 0.0995 g (0.216 mmol) of compound (101-4), 0.0013 g (0.011 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.0039 g (0. 021 mmol) was added with 2 mL of dry N, N-dimethylformamide and 0.5 mL of triethylamine, and the mixture was stirred at room temperature. 0.024 mL (0.22 mmol) of ethynylbenzene was added dropwise to the reaction mixture, and the mixture was stirred at 60 ° C. for 3 hours. The solvent was distilled off, and the obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 70/30) to obtain 0.056 g of compound (101) (yield, 62.8%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.74-8.65 (m, 4H), δ8.18 (s, 1H), δ7.96 (d, J = 2.8 Hz, 1H), δ7.94 (D, J = 3.6Hz, 1H), δ7.82 (d, J = 1.6Hz, 8.8Hz, 1H), δ7.76 (s, 1H), δ7.62-7.60 (m, 2H), δ7.82 (d, J = 1.6Hz, 8.8Hz, 1H), δ7.39-7.36 (m, 4H), δ2.85 (t, J = 7.5Hz, 2H), δ1.77-1.71 (m, 2H), δ1.46-1.24 (m, 6H), δ0.90 (t, J = 7.0Hz, 3H).

<Evaluation of solubility of compound (101)>
At room temperature (25 ° C.), p-xylene was added to compound (101) until it was completely dissolved visually and the solubility was evaluated. The results are shown in Table 1.

<Method for manufacturing a transistor using compound (101)>
Platinum is patterned through a metal mask on a glass substrate that has been ultrasonically washed (30 minutes x 3 times each) in this order using a neutral detergent aqueous solution, distilled water, acetone, and ethanol by a sputtering method. A gate electrode is formed by vapor deposition (thickness: 30 nm), and further, a gate made of a dichloro-di-p-xylylene polymer (polyparaxylylene) is used so as to cover the gate electrode by a thermal CVD method. An insulating layer was formed (thickness: 1 μm).
Next, a source / drain electrode is formed by pattern-depositing gold on the gate insulating layer via a metal mask by a vacuum vapor deposition method (2 × ^{10-6 Torr) (thickness: 20 nm,} Channel length: channel width = 75 μm: 3000 μm), which was immersed in an ethanol solution of pentafluorobenzenethiol (concentration: 0.08% by mass) for 1 hour and then rinsed with ethanol.
Finally, 0.05 μL of a p-xylene solution (0.4% by mass) of compound (101) was drop-cast so as to cover the source / drain electrodes, and dried at room temperature to form a semiconductor layer.

<Method of evaluating the mobility of a transistor using compound (101)>
The mobility of the transistor manufactured as described above is determined by applying a voltage (V _g ) to the gate electrode while sweeping (+ 40 V to -60 V) with the source electrode grounded and -80 V applied to the drain electrode. Measure the _{current (Id} ) flowing through the drain electrode and
From the slope of √I _d -V _g, it was determined by using the equation (Eq.101). The unit is cm ² / Vs.

_{I d = (W / 2L)} · C · μ · (V g -V T) 2 (Eq.101)

(In the equation, W is the channel width, L is the channel length, μ is the mobility, C is the capacitance per unit area of the gate insulating layer, and _VT is the threshold voltage.)
The results are shown in Table 2.

<Evaluation of heat resistance of compound (101)>
The transistor produced as described above was placed on a hot plate heated to 100 ° C. and held for 5 minutes. The mobility of the heat-treated transistor was determined in the same manner as before the heat treatment. The results are shown in Table 2.

(Example 2)
<Method for producing compound (102)>
A method for producing the compound (102) will be described. The compound (102) is a compound represented by the general formula (1), which corresponds to the case where ^{Ar is a 2-thienyl group and R 1 is a hexyl group.}

The manufacturing scheme is shown in (S102).

The method for synthesizing compound (102) will be described below.
Under an argon atmosphere, 0.101 g (0.219 mmol) of compound (101-4), 0.0019 g (0.016 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.0056 g (0. To 029 mmol), 2 mL of dry N, N-dimethylformamide and 1 mL of triethylamine were added, and the mixture was stirred at room temperature. After 0.025 mL (0.22 mmol) of 2-ethynylthiophene was added dropwise to the reaction mixture, the mixture was stirred at 60 ° C. for 2 hours. The solvent was distilled off, and the obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 70/30) to obtain 0.073 g of compound (102) (yield, 79.5%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.74-8.64 (m, 4H), δ8.17 (d, J = 2.0 Hz, 1H), δ7.98 (d, J = 5.8 Hz, 1H), δ7.95 (d, J = 5Hz, 1H), δ7.80 (d, J = 2.0Hz, 8.8Hz, 1H), δ7.78 (s, 1H), δ7.57 (d, J = 1.8Hz, 8.6Hz, 1H), δ7.36-7.32 (m, 2H), δ7.07-7.04 (m, 1H), δ2.86 (t, J = 7.8Hz) , 2H), δ1.81-1.70 (m, 2H), δ1.46-1.26 (m, 6H), δ0.90 (t, J = 7.2Hz, 3H).

<Evaluation of solubility of compound (102)>
In Example 1, the solubility was evaluated in the same manner as in Example 1 except that compound (102) was used instead of compound (101). The results are shown in Table 1.

<Method for manufacturing a transistor using compound (102)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (102) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (102)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (102) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (102)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (102) was used instead of compound (101). The results are shown in Table 2.

(Example 3)
<Method for producing compound (103)>
The method for producing the compound (103) will be described. The compound (103), in the compound represented by the general formula (1) is a compound wherein Ar is 4-pentylphenyl group, R ¹ is equivalent to the case of octyl group.

The manufacturing scheme is shown in (S103).

（Ｓ１０３）
まず、化合物（１０３−１）の合成方法について説明する。
アルゴン雰囲気下、化合物（１０１−３）０．６２２ｇ（１．１９ｍｍｏｌ）、アセチルアセトン鉄（ＩＩＩ）０．０４２０ｇ（０．１１９ｍｍｏｌ）に脱水テトラヒドロフラン１２ｍＬ、Ｎ−メチルピロリドン０．６ｍＬを加え、０℃で撹拌した。反応液へオクチルマグネシウムブロミドの２．０Ｍエーテル溶液０．８０ｍＬ（１．６ｍｍｏｌ）を滴下した後、３０分撹拌した。反応液へ水を加えて反応を停止した後、セライトろ過を行った。ろ液を濃縮し得られた固体をシリカゲルカラムクロマトグラフィー（ヘキサン／クロロホルム＝１００／０→６０／４０）で分離精製を行い、化合物（１０３−１）０．２１５ｇ（収率、３７．１％）を得た。
^１Ｈ ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ_３）：δ８．８５−８．７９（ｍ，２Ｈ），δ８．６９（ｄ，Ｊ＝８．８Ｈｚ，１Ｈ），δ８．６３（ｄ，Ｊ＝９．２Ｈｚ，１Ｈ），δ８．０２−７．９７（ｍ，２Ｈ），δ７．８８（ｄ，Ｊ＝２．４Ｈｚ，１Ｈ），δ７．７９（ｓ，１Ｈ），δ７．６２−７．５６（ｍ，２Ｈ），δ２．８６（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ），δ１．８１−１．７２（ｍ，２Ｈ），δ１．４７−１．２４（ｍ，１０Ｈ），δ０．９３（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）．

(S103)
First, a method for synthesizing compound (103-1) will be described.
Under an argon atmosphere, add 12 mL of dehydrated tetrahydrofuran and 0.6 mL of N-methylpyrrolidone to 0.622 g (1.19 mmol) of compound (101-3) and 0.0420 g (0.119 mmol) of acetylacetone iron (III) at 0 ° C. Stirred. 0.80 mL (1.6 mmol) of a 2.0 M ether solution of octylmagnesium bromide was added dropwise to the reaction mixture, and the mixture was stirred for 30 minutes. Water was added to the reaction solution to stop the reaction, and then Celite filtration was performed. The solid obtained by concentrating the filtrate was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 60/40) to obtain 0.215 g of compound (103-1) (yield, 37.1%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.85-8.79 (m, 2H), δ8.69 (d, J = 8.8 Hz, 1H), δ8.63 (d, J = 9.2 Hz, 1H), δ8.02-7.97 (m, 2H), δ7.88 (d, J = 2.4Hz, 1H), δ7.79 (s, 1H), δ7.62-7.56 (m, 2H), δ2.86 (t, J = 7.6Hz, 2H), δ1.81-1.72 (m, 2H), δ1.47-1.24 (m, 10H), δ0.93 (t, J = 7.2Hz, 3H).

Finally, a method for synthesizing compound (103) will be described.
Under an argon atmosphere, 0.101 g (0.211 mmol) of compound (103-1), 0.0017 g (0.014 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.0047 g (0. To 025 mmol), 1.2 mL of dry N, N-dimethylformamide and 0.65 mL of triethylamine were added, and the mixture was stirred at room temperature. After 0.074 mL (0.38 mmol) of 1-ethynyl-4-pentylbenzene was added dropwise to the reaction mixture, the mixture was stirred at 60 ° C. for 2 hours. The solvent was distilled off, and the obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 70/30) to obtain 0.073 g of compound (103) (yield, 40.9%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.74-8.64 (m, 4H), δ8.17 (d, J = 1.6 Hz, 1H), δ7.97 (d, J = 4.0 Hz, 1H), δ7.95 (d, J = 4.0Hz, 1H), δ7.80 (d, J = 1.6Hz, 8.8Hz, 1H), δ7.77 (d, J = 1.6Hz, 1H) ), δ7.57 (d, J = 1.6Hz, 8.8Hz, 1H), δ7.52 (d, J = 8.0Hz, 2H), δ7.20 (d, J = 8.0Hz, 2H) , Δ2.85 (t, J = 7.8Hz, 2H), δ2.65 (t, J = 7.8Hz, 2H), δ1.81-1.74 (m, 2H), δ1.68-1. 62 (m, 2H), δ1.43-1.23 (m, 14H), δ0.93-0.86 (m, 6H).

<Evaluation of solubility of compound (103)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (103) was used instead of compound (101). The results are shown in Table 1.

<Method for manufacturing a transistor using compound (103)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (103) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (103)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (103) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (103)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (103) was used instead of compound (101). The results are shown in Table 2.

(Example 4)
<Method for producing compound (104)>
A method for producing the compound (104) will be described. The compound (104) is a compound represented by the general formula (1), which corresponds to the case where ^{Ar is a 4-pentylphenyl group and R 1 is a decyl group.}

The manufacturing scheme is shown in (S104).

(S104)

First, a method for synthesizing compound (104-1) will be described.
Under an argon atmosphere, add 20 mL of dehydrated tetrahydrofuran and 1.0 mL of N-methylpyrrolidone to 1.00 g (1.91 mmol) of compound (101-3) and 0.0658 g (0.186 mmol) of iron (III) acetylacetone, and at 0 ° C. Stirred. 3.0 mL (3.0 mmol) of a 1.0 M ether solution of decylmagnesium bromide was added dropwise to the reaction mixture, and the mixture was stirred for 30 minutes. Water was added to the reaction solution to stop the reaction, and then Celite filtration was performed. The solid obtained by concentrating the filtrate was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 60/40) to obtain 0.388 g of compound (104-1) (yield, 39.4%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.85-8.79 (m, 2H), δ8.69 (d, J = 8.8 Hz, 1H), δ8.62 (d, J = 8.8 Hz, 1H), δ8.02-7.97 (m, 2H), δ7.88 (d, J = 2.4Hz, 1H), δ7.79 (s, 1H), δ7.61-7.56 (m, 2H), δ2.86 (t, J = 7.6Hz, 2H), δ1.81-1.72 (m, 2H), δ1.47-1.20 (m, 14H), δ0.87 (t, J = 6.8Hz, 3H).

Finally, a method for synthesizing compound (104) will be described.
Under an argon atmosphere, 0.129 g (0.250 mmol) of compound (104-1), 0.0018 g (0.016 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.0080 g (0. To 042 mmol), 1.5 mL of dry N, N-dimethylformamide and 0.60 mL of triethylamine were added, and the mixture was stirred at room temperature. After 0.070 mL (0.36 mmol) of 1-ethynyl-4-pentylbenzene was added dropwise to the reaction mixture, the mixture was stirred at 60 ° C. for 2 hours. The solvent was distilled off, and the obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 70/30) to obtain 0.063 g of compound (104) (yield, 46.8%). ) Was obtained.
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.73-8.64 (m, 4H), δ8.17 (d, J = 1.6 Hz, 1H), δ7.97 (d, J = 3.6 Hz, 1H), δ7.95 (d, J = 3.2Hz, 1H), δ7.80 (d, J = 1.6Hz, 8.8Hz, 1H), δ7.77 (d, J = 1.6Hz, 1H) ), δ7.57 (d, J = 2.0Hz, 8.4Hz, 1H), δ7.52 (d, J = 8.2Hz, 2H), δ7.20 (d, J = 8.2Hz, 2H) , Δ2.86 (t, J = 7.6Hz, 2H), δ2.64 (t, J = 7.5Hz, 2H), δ1.81-1.72 (m, 2H), δ1.70-1. 60 (m, 2H), δ1.44-1.23 (m, 18H), δ0.93-0.85 (m, 6H).

<Evaluation of solubility of compound (104)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (104) was used instead of compound (101). The results are shown in Table 1.

<Method for manufacturing a transistor using compound (104)>
A transistor was produced in the same manner as in Example 1 except that compound (104) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (104)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (104) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (104)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (104) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 1)
<Method for producing compound (C101)>

The production scheme of compound (C101) is shown in (C101).

The method for synthesizing the compound (C101) will be described below.
Under an argon atmosphere, 0.911 g (1.74 mmol) of compound (101-3), 0.0989 g (0.498 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.0163 g (0. To 500 mmol), 8.5 mL of dry N, N-dimethylformamide and 4.3 mL of triethylamine were added, and the mixture was stirred at room temperature. After adding 0.42 mL (3.8 mmol) of ethynylbenzene to the reaction mixture, the mixture was stirred at 60 ° C. for 2 hours. The solvent was distilled off, and the obtained crude product was separated and purified by silica gel column chromatography (hexane / chloroform = 100/0 → 70/30) to obtain 0.420 g (yield, 50.7) of compound (C101). Got
^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.76-8.71 (m, 4H), δ8.2.0 (s, 2H), δ8.01 (d, J = 10.4 Hz, 2H), δ7 .84 (d, J = 8.8Hz, 2H), δ7.64-7.60 (m, 4H), δ7.42-7.37 (m, 6H).

<Evaluation of solubility of compound (C101)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C101) was used instead of compound (101). The results are shown in Table 1.

<Method for manufacturing a transistor using compound (C101)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C101) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C101)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C101) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C101)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C101) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 2)
<Method for producing compound (C102)>
Compound (C102) was produced according to the synthetic method described in Patent Document 3.

^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.69-8.65 (m, 4H), δ7.94 (d, J = 9.2 Hz, 2H), δ7.78 (s, 2H), δ7.56 -7.53 (m, 2H), δ2.85 (t, J = 7.6Hz, 4H), δ1.80-1.72 (m, 4H), δ1.42-1.32 (m, 12H) , Δ0.90 (t, J = 7.2Hz, 6H).

<Method for manufacturing a transistor using compound (C102)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C102) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C102)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C102) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C102)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C102) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 3)
<Method for producing compound (C103)>
Compound (C103) was produced according to the synthetic method described in Patent Document 3.

^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.69-8.65 (m, 4H), δ7.94 (d, J = 8.8 Hz, 2H), δ7.76 (s, 2H), δ7.56 -7.54 (m, 2H), δ2.85 (t, J = 7.8Hz, 4H), δ1.82-1.72 (m, 4H), δ1.46-1.31 (m, 20H) , Δ0.88 (t, J = 6.6Hz, 6H).

<Method for manufacturing a transistor using compound (C103)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C103) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C103)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C103) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C103)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C103) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 4)
<Method for producing compound (C104)>
Compound (C104) was produced according to the synthetic method described in Patent Document 3.

^{1 1} H NMR (400 MHz, CDCl ₃ ): δ8.69-8.65 (m, 4H), δ7.94 (d, J = 9.2 Hz, 2H), δ7.76 (s, 2H), δ7.55 -7.54 (m, 2H), δ2.85 (t, J = 7.8Hz, 4H), δ1.81-1.71 (m, 4H), δ1.45-1.19 (m, 28H) , Δ0.88 (t, J = 6.6Hz, 6H).

<Method for manufacturing a transistor using compound (C104)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C104) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C104)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C104) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C104)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C104) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 5)
<Method for producing compound (C105)>
Compound (C105) was produced according to the synthetic method described in Patent Document 3.

<Method for manufacturing a transistor using compound (C105)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C105) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C105)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C105) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C105)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C105) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 6)
<Method for producing compound (C106)>
Compound (C106) was produced according to the synthetic method described in Patent Document 2.

<Evaluation of solubility of compound (C106)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C106) was used instead of compound (101). The results are shown in Table 1.

(Comparative Example 7)
<Method for producing compound (C107)>
Compound (C107) was produced according to the synthetic method described in Patent Document 2.

<Method for manufacturing a transistor using compound (C107)>
In Example 1, a transistor was manufactured in the same manner as in Example 1 except that compound (C107) was used instead of compound (101).

<Method of evaluating the mobility of a transistor using compound (C107)>
In Example 1, the mobility of the transistor was evaluated in the same manner as in Example 1 except that the transistor made of compound (C107) was used instead of the transistor made of compound (101). The results are shown in Table 2.

<Evaluation of heat resistance of compound (C107)>
In Example 1, the heat resistance was evaluated in the same manner as in Example 1 except that compound (C107) was used instead of compound (101). The results are shown in Table 2.

(Comparative Example 8)
<Method for producing compound (C108)>
Compound (C108) was produced according to the synthetic method described in Patent Document 1.

<Evaluation of solubility of compound (C108)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C108) was used instead of compound (101). The results are shown in Table 1.

(Comparative Example 9)
<Method for producing compound (C109)>
Compound (C109) was produced according to the synthetic method described in Patent Document 4.

<Evaluation of solubility of compound (C109)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C109) was used instead of compound (101). The results are shown in Table 1.

(Comparative Example 10)
<Method for producing compound (C110)>
Compound (C110) was produced according to the synthetic method described in Patent Document 4.

<Evaluation of solubility of compound (C110)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C110) was used instead of compound (101). The results are shown in Table 1.

(Comparative Example 11)
<Method for producing compound (C111)>
Compound (C111) was produced according to the synthetic method described in Patent Document 4.

<Evaluation of solubility of compound (C111)>
In Example 1, the solubility was evaluated in the same manner as in Example 2 except that compound (C111) was used instead of compound (101). The results are shown in Table 1.

(Table 1)

(Table 2)

As is clear from Table 1, the compound of the present invention exhibits high solvent solubility of 1.0% by mass or more even at room temperature. On the other hand, compounds of comparative examples (those having a di (arylethynyl) group in the chrysene skeleton (Comparative Example 1), those having an alkyl group and an aryl group in the chrysene skeleton (Patent Document 2, Comparative Example 6), chrysene Those having a diaryl group in the skeleton (Patent Document 1, Comparative Example 8) and those in which the chrysene skeleton in the compound of the present invention is another polycyclic aromatic (Patent Document 4, Comparative Example 9-11) are solvents. The solubility is inferior to less than 1.0% by mass (the higher the solubility, the higher the suitability for ink and the industrial advantage).

From Table 2, the film is formed by the drop casting method (the drop casting method is a highly practical film forming method having a correlation with the inkjet method among the wet film forming methods) using the compound of the present invention. The transistor having the semiconductor layer ^{shows a high mobility of 1.0 cm 2} / Vs or more, and the mobility does not decrease even if heat treatment is performed (it may be deteriorated by external heat after mounting). It is highly reliable in practical use.) On the other hand, the mobility of the transistor manufactured under the same conditions and using the compound of the comparative example is greatly reduced by the heat treatment.
From the above, it can be seen that since the compound of the present invention has high solvent solubility, it provides a semiconductor device that exhibits high mobility by the wet film forming method and does not decrease in mobility due to heat.

The compound of the present invention can be used as a semiconductor, and can be used in a semiconductor device using the semiconductor as a semiconductor layer.

1. 1. Substrate 2. Gate electrode 3. Gate insulating layer 4. Semiconductor layer 5. Source electrode 6. Drain electrode

Claims (6)

A compound represented by the general formula (1).

(In the formula, Ar represents the general formula (2) or the general formula (3), and R ¹ represents a linear alkyl group having 1 to 20 carbon atoms . )

(In the formula, X ²¹ , X ²² , X ²⁴ , and X ²⁵ represent a hydrogen atom, X ²³ represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms, and * represents a monovalent substituent. Represents the joint hand of.)

(In the formula, X ³² and X ³³ represent a hydrogen atom, X ³¹ represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms, and * represents a bond as a monovalent substituent.) A semiconductor material containing the compound according to claim 1. An ink containing the compound according to claim 1. A semiconductor film containing the compound according to claim 1. A semiconductor device having a semiconductor layer containing the compound according to claim 1. A transistor having a semiconductor layer containing the compound according to claim 1.

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