JP2014133713A - Dinaphthofuran compound and organic semiconductor device using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To disclose a novel organic semiconductor compound with high carrier mobility and durability, and to provide a use thereof as an organic semiconductor device.SOLUTION: An organic semiconductor device uses a 21DNFU derivative shown below as a semiconductor (in chemical formula [1], Arand Arrespectively represent an aryl group or a heterocyclic group, and each of Rand Ris selected from any of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a carbonyl group, an ester group, an amide group, an imino group, a sulfide group, a sulfoxide group, a sulfonyl group, a silyl group, a nitro group, a nitrile group, and a mercapto group).

Description

The present invention relates to a dinaphthofuran compound which is a novel compound, a synthesis method thereof, and an organic semiconductor device using the same.

An organic transistor is a transistor that uses an organic semiconductor for its semiconductor layer. When a thin film of several tens of nanometers is used as a semiconductor, it is called an organic thin film transistor (OTFT). The mechanism is the same as that of an inorganic transistor using an inorganic material such as silicon. By changing the voltage applied to the gate electrode, the current flowing in the organic semiconductor between the source electrode and the drain electrode can be turned on / off. it can. An organic substance such as an organic semiconductor is mainly bonded by an intermolecular force (Van der Waals force), and therefore has higher flexibility than an atomic bond substance such as a Si crystal. Therefore, it can be manufactured by vapor deposition or coating on a plastic substrate, and it is possible to manufacture an electronic device that is lighter, thinner, and bent than a substrate using Si crystal.

The operating frequency of the organic transistor varies mainly depending on the organic semiconductor material and the structure of the transistor, and improves as the carrier mobility of the organic semiconductor increases. Organic semiconductors are said to have lower carrier mobility than inorganic semiconductors and have difficulties in durability such as oxidation resistance and heat resistance. Furthermore, the quality of the organic semiconductor in the solvent is closely related to the method of forming the thin film, and attention has been paid to the development of a new organic semiconductor and its manufacturing technology.

There are many prior arts related to organic semiconductors. As a recent prior art, organic semiconductor compounds having a structure in which a thiophene ring or a selenophene ring is bonded to both benzene rings of naphthalene (Patent Document 1), at least one aromatic ring having a substituent, and an unsubstituted aromatic It has a repeating unit having a partial structure in which at least one of the group rings is linked, and contains a compound having Head-To-Tail type stereoregularity in the repeating unit. An organic semiconductor material (Patent Document 2), a compound such as dinaphthothienothiophene that enables formation of an organic semiconductor layer composed of a condensed polycyclic aromatic compound using a solution method that is generally easier than a vapor deposition method, and hexachloro There are novel addition compounds having a structure in which a compound having a double bond such as cyclopentadiene is detachably added (Patent Document 3) and othersFurther, a dinaphthofuran derivative and an aromatic diacetylene compound, which can be suitably used for a polymeric fluorescent substance layer constituting an organic EL element, wherein the main chain includes a repeating unit represented by a specific formula Polyarylene ethynylene (Patent Document 4) produced by increasing the molecular weight by polycondensation reaction can be seen.

On the other hand, the inventors of the present application have also made research on organic semiconductors and their physical properties and filed patent applications (Patent Documents 5 to 7). Conventional organic semiconductors have used a method of adding a functional group to an organic semiconductor in order to increase the solubility in a solvent. This time, a new organic semiconductor having excellent solubility in an organic solvent and low manufacturing cost was found, and it was revealed that its electronic characteristics were particularly effective, and this patent application is filed.

JP 2010-150229 A JP 2006-222251 A JP 2011-168869 A JP 2009-215425 A JP 2009-302264 A JP 2010-118415 A JP 2011-111977

The problem to be solved by the present invention is to provide an organic semiconductor material having high carrier mobility and excellent atmospheric stability and a semiconductor device using the same.

The first invention is a dinaphthofuran compound represented by the following chemical formula [1].
(In the chemical formula [1], Ar ¹ and Ar ² each represent an aryl group or a heterocyclic group, and R ¹ and R ² represent a hydrogen atom and a deuterium atom, a halogen atom, an alkyl group, an alkenyl group, (Selected from alkynyl group, alkoxyl group, carbonyl group, ester group, amide group, imino group, sulfide group, sulfoxide group, sulfonyl group, silyl group, nitro group, nitrile group, and mercapto group.)

The aryl group is not particularly limited, and examples thereof include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, and 2-phenanthryl group. 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 3-styrylphenyl group, 4-styrylphenyl group, 1-pyrenyl group, 2- Pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl 2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, fluoreni Group, stilbenyl group, pyrenyl group, etc. perylenyl group.

The heterocyclic group is not particularly limited. For example, thienyl group, N-carbazoyl group, benzothiazole group, benzotriazole group, pyrrolyl group, furyl group, pyridyl group, pyrimidyl group, triazyl group, thiazolyl group, oxazoyl group Oxadiazolyl group, thiadiazolyl group, diazaphenylenyl group, and the like.

The halogen atom is not particularly limited, and examples thereof include fluorine, chlorine, bromine and iodine. The alkyl group may be linear, branched or cyclic, and preferably has 1 to 20 carbon atoms. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, 2-ethylhexyl group, Examples include heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, cyclohexyl group, cyclopentyl group, cyclobutyl group, and cyclooctyl group.

The alkenyl group is not particularly limited, and examples thereof include ethenyl group, methylethenyl group, hexylethenyl group, phenylethenyl group (o-butylphenyl) ethenyl group, (m-butylphenyl) ethenyl group, and (p-butylphenyl) ethenyl. Group, naphthylethenyl group, biphenylethenyl group, terphenylethenyl group, perfluorophenylethenyl group and the like.

The alkynyl group is not particularly limited, and examples thereof include ethynyl group, methylethynyl group, octylethynyl group, (o-butylphenyl) ethynyl group, (m-butylphenyl) ethynyl group, (p-butylphenyl) ethynyl group, Examples include naphthylethynyl group, biphenylethynyl group, terphenylethynyl group, trimethylsilylethynyl group, triethylsilylethynyl group, triisopropylsilylethynyl group, and the like.

The alkoxyl group is not particularly limited, and may be linear, branched or cyclic. For example, methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group Decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, cyclohexyloxy group, cyclopentyloxy group, cyclobutyloxy group, cyclooctyloxy group and the like.

The ester group is not particularly limited, and examples thereof include a methyl ester group, an ethyl ester group, a propyl ester group, a butyl ester group, a phenyl ester group, a naphthyl ester group, a cyclohexyl ester group, and a cyclopentyl ester group.

The amide group is not particularly limited, and examples thereof include an acetamido group, a propylamide group, a butylamide group, an isobutylamide group, a pentylamide group, an isopentylamide group, a hexylamide group, and an octylamide group.

The imino group is not particularly limited, and examples thereof include a methylimino group, an ethylimino group, a propylimino group, a butylimino group, a pentylimino group, a hexilimino group, a heptilimino group, an octylimino group, a phenylimino group, and a naphthylimino group.

The sulfide group is not particularly limited, for example, methyl sulfide group, ethyl sulfide group, propyl sulfide group, isopropyl sulfide group, butyl sulfide group, isobutyl sulfide group, pentyl sulfide group, hexyl sulfide group, heptyl sulfide group, octyl sulfide group , Phenyl sulfide group, naphthyl sulfide group and the like.

The sulfoxide group is not particularly limited, and for example, methyl sulfoxide group, ethyl sulfoxide group, propyl sulfoxide group, isopropyl sulfoxide group, butyl sulfoxide group, isobutyl sulfoxide group, sec-butyl sulfoxide group, tert-butyl sulfoxide group, pentyl sulfoxide group Hexyl sulfoxide group, heptyl sulfoxide group, octyl sulfoxide group, phenyl sulfoxide group, o-hexylphenyl sulfoxide group, m-hexylphenyl sulfoxide group, p-hexylphenyl sulfoxide group and the like.

The sulfonyl group is not particularly limited. For example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, various pentylsulfonyl groups. Groups, various hexylsulfonyl groups, various heptylsulfonyl groups, various octylsulfonyl groups, phenylsulfonyl groups, o-hexylphenylsulfonyl groups, m-hexylphenylsulfonyl groups, p-hexylphenylsulfonyl groups and the like.

The silyl group is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, a triisobutylsilyl group, a tripropylsilyl group, a triisopropylsilyl group, a trisec-butylsilyl group, and a tritert-butylsilyl group. Can be mentioned.

Here, Ar ¹ and Ar ² may be different from each other, but are preferably the same substituent from the viewpoint of ease of production, and R ¹ and R ² are also similarly easy to produce. From this point of view, the same substituent is preferable. More preferably, Ar ¹ and Ar ² are the same substituents, and R ¹ and R ² are the same substituents.

Next, a method for producing the compound of the present invention will be described.
The compound of the present invention represented by the formula (1) can be produced by combining known methods for synthesizing organic compounds, but the compound of claim 1 can be easily produced by using the method of the second invention. I found.

In the second invention, dinaphtho [2,1-b: 1 ′, 2′-d] furan (hereinafter abbreviated as 21DNFU) is halogenated and 4,4′-dihalodinaphtho [2,1-b: 1 ′, 2′-d] is a production method for producing the dinaphthofuran compound of the first invention via reaction with boronic acid or a derivative thereof after being converted to furan.

A known method can be used for the halogenation. Specifically, for example, chlorine, bromine, iodine, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide and the like can be used.

A boronic acid or a derivative thereof is a compound having a boronic acid, a compound in which one or more hydrogen atoms of the boronic acid are substituted, a boronic acid ester which may form a ring, and a boroxine ring.

In that case, a base and a metal compound can be used as a catalyst. For example, as the base, alkali metal or alkaline earth metal hydroxides, carbonates, hydrogen carbonates, phosphates, carboxylates and alkoxides, and tertiary amines can be used. Of these, alkali metal or alkaline earth metal hydroxides, carbonates, hydrogen carbonates, phosphates and carboxylates are preferably used. More preferred are alkali metal or alkaline earth metal carbonates and hydrogen carbonates. Specific examples include sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, and the like.

As a metal compound which can be used as a catalyst in the process of the second invention, one or more metals selected from palladium, nickel and iron are used alone or in combination of two or more. Among these, those containing palladium are preferable. Specifically, for example, palladium (0) / carbon, palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tetrakis (triphenylphosphine) palladium (0), palladium ketoner , Palladium acetylacetonate, nitrile palladium halide, palladium halide, allyl palladium halide, palladium biscarboxylate and the like.

The purity of the dinaphthofuran compound produced by the method of the second invention can be increased by a known method. Specifically, for example, methods such as zone purification, sublimation purification, column chromatography, thermal washing, distillation, and recrystallization can be used.

The third invention is characterized in that the halogen atom content is less than 10 ppm, the palladium atom content is less than 10 ppm, and the boron atom content is 10 ppm or less. A compound.

Here, the halogen atom is fluorine, chlorine, bromine or iodine.
The purity of the organic semiconductor has a great influence on the characteristics of the organic semiconductor device. In the process of the second invention, the reaction rate is high and the purity can be raised relatively easily. By combining one or more of the above-mentioned methods, it is possible to obtain a highly pure compound of the third invention.

The amount of palladium atoms can be quantified by a known analysis method. Specifically, for example, it can be quantified by using atomic absorption or ICP-MS.
Known amounts of analysis can be used for the amount of halogen atoms. Specifically, for example, the sample can be quantified by using a potentiometric titration method or ion chromatography after combustion decomposition.
The amount of boron atoms can be quantified by a known analysis method. Specifically, for example, it can be quantified by using inductively coupled plasma-luminescence or inductively coupled plasma-mass spectrometry.

The dinaphthofuran skeleton has optical isomers and has an R-form or S-form structure as shown in the chemical formula [2].

A fourth invention is the compound according to any one of the first invention and the third invention, wherein a compound having either a dinaphthofuran skeleton of R form or S form is selectively used.

That is, the R-form or S-form compound is not the same amount, but has a composition close to either one. Normally, either one of the R-form or S-form is mixed with a compound of only one of the compounds rather than a mixture of R-form or S-form. It is preferable to be biased toward one compound.

The determination of the R or S body can be made using a polarimeter. The method for producing either the R-form or the S-form compound can be produced by using optically resolved dinaphthofuran as a raw material. It can also be produced by isolating either one from a mixture of R or S compounds using optical resolution column chromatography or the like.

In order to utilize the compound of the present invention for an organic semiconductor device, it is mainly used in the form of a thin film, and either a wet process or a dry process may be used as a method for forming the thin film. In a wet process with great industrial merit, solubility in an organic solvent or the like is important.

Here, examples of the organic solvent include halogen solvents such as dichloromethane, chloroform, chlorobenzene, fluorobenzene, 1,1,2,2-tetrachloroethane, and alcohols such as cyclohexanol, ethanol, isopropyl alcohol, butanol, and octanol. Solvents, ketone solvents such as cyclohexanone, acetone and methyl ethyl ketone, aromatic hydrocarbon solvents such as toluene, xylene and methyl naphthalene, ester solvents such as ethyl acetate, γ-butyl lactone and propylene carbonate, N, N-dimethylformamide Amide solvents such as N-methylpyrrolidone, ether solvents such as tetrahydrofuran, diethyl ether and anisole, nitrile solvents such as acetonitrile, propionitrile and benzonitrile, dimethyl Sulfoxides, such as sulfur-based solvents such as sulfolane, known materials can be used so far. One or a mixture of two or more of these solvents may be used.

When the compound of the present invention is dissolved in an organic solvent or the like, the temperature and pressure are not particularly limited, but the temperature is preferably in the range of 0 to 200 ° C, more preferably in the range of 10 to 150 ° C. Regarding the pressure, a range of 0.1 to 100 MPa is preferable, and a range of 0.1 to 10 MPa is more preferable. Moreover, it is also possible to use something like supercritical carbon dioxide instead of the organic solvent. The adjustment of the solution can be performed in air, but it is preferably performed in an inert atmosphere such as nitrogen or argon.

The wet process is a spin coating method, a dip coating method, a bar coating method, a spray coating method, an ink jet method, a screen printing method, a lithographic printing method, an intaglio printing method, a letterpress printing method, an electric field polymerization method, a chemical polymerization method, a blade. The coating method, Langmuir-Blodgett method, die coating method and the like are shown, and these known methods can be used.

The dry process refers to a vacuum deposition method, sputtering, CVD method, low energy ion beam method, ion plating method, plasma polymerization method, laser deposition method, molecular beam epitaxial growth method, vapor phase transport growth method, etc. These known methods can be used.

5th invention is the organic transistor manufactured using the dinaphthofuran compound in any one of 1st invention, 3rd invention, and 4th invention.

The organic transistor will be described. The organic transistor of the present invention includes at least a source electrode, a drain electrode, a gate electrode, an insulator layer, and an organic semiconductor layer. When producing an organic transistor, the organic semiconductor material is mainly used in the form of a thin film, and either a wet process or a dry process may be used as the thin film production method.

The wet process and the dry process are as described above. Moreover, when applying a wet process, it is necessary to make an organic-semiconductor material into a solution, About an organic solvent, it is as above-mentioned.

In the organic transistor of the present invention, a source electrode, a drain electrode, and a gate electrode are used, but the conductive material is not particularly limited. For example, gold, copper, silver, nickel, chromium, iron, tin, aluminum , Indium, palladium, germanium, calcium, sodium, potassium, magnesium, manganese, titanium, lithium, zinc, tungsten, molybdenum, tin oxide, indium oxide, silver paste, carbon paste, ITO, PEDOT / PSS, and the like. These electrodes may use one kind or a mixture of two or more kinds.

When used for an organic semiconductor device, the insulator layer is not particularly limited, and any insulating material can be suitably used. Examples thereof include inorganic oxides such as silicon oxide film (SiO ₂ ) and alumina (Al ₂ O ₃ ), organic polymers such as polystyrene, polyethylene, polymethyl methacrylate, polyethyl acrylate, CYTOP, and polytetrafluoroethylene. be able to.

In the organic transistor of the present invention, the organic semiconductor layer may be subjected to a doping treatment. As the dopant, a donor-type dopant and an acceptor-type dopant can be used. As the donor dopant, any compound that can donate electrons to the organic semiconductor can be preferably used. For example, alkali metals such as lithium, sodium and potassium, and alkaline earth metals such as calcium, strontium and barium. Rare earth metals such as yttrium, lanthanum and europium. Cations such as tetraalkylammonium and tetraalkylphosphonium can be mentioned.

As the acceptor dopant, any compound that can remove electrons from an organic semiconductor can be preferably used. For example, halogen compounds such as chlorine, bromine, iodine, iodine chloride, iodine bromide. Lewis acids such as phosphorus pentafluoride, boron trifluoride, boron trichloride and boron tribromide, proton acids such as hydrogen fluoride, sulfuric acid and nitric acid, and organic acids such as acetic acid, formic acid and amino acids. Examples include transition metal compounds such as iron trichloride, titanium tetrachloride, zirconium tetrachloride, tungsten pentafluoride, tungsten hexachloride, electrolyte anions such as chloride ions, bromide ions, iodide ions, and sulfonate anions.

Moreover, in order to protect the organic transistor of this invention from a physical damage, a protective layer can also be provided in the whole surface or a part of organic transistor. The material for forming the protective layer is not particularly limited, and organic compounds such as polymethyl methacrylate, parylene, polystyrene, polyacrylonitrile, polyimide, polyamide, polyvinyl phenol, polyvinyl alcohol, polyvinylidene fluoride, cyanoethyl pullulan, and silicon oxide. Inorganic compounds such as aluminum oxide, tantalum oxide, titanium oxide, tin oxide, barium titanate, and strontium titanate can be used.

A novel organic semiconductor compound with low production cost and durability is disclosed, and the use as an organic semiconductor device is provided.

FIG. 1 is an output characteristic curve of a 3P-21DNFU single crystal transistor. FIG. 2 is a transfer characteristic curve of a 3P-21DNFU single crystal transistor.

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto.

(Synthesis of Br-21DNFU)
A 500 ml four-necked flask equipped with a thermometer, a condenser tube, and a magnetic stirrer was charged with 10 g of dinaphtho [2,1-b: 1 ′, 2′-d] furan and 200 ml of dimethylformamide and stirred at room temperature. . Thereafter, a solution prepared by dissolving 14.4 g of N-bromosuccinimide in 200 ml of dimethylformamide was added dropwise over 100 minutes while cooling using an ice bath so that the reaction solution became 5 ° C. The ice bath was then removed and the mixture was stirred at room temperature for 4 days. The reaction solution was poured into 700 ml of ice water, and the precipitate (crude material) was collected by filtration. The obtained crude product was recrystallized using 1,2-dichloromethane to obtain 12.41 g of light brown crystals.

(Synthesis of P-21DNFU)
In a 50 ml three-necked flask equipped with a thermometer, condenser, and magnetic stirrer, 0.5 g of 4,4′-dibromodinaphtho [2,1-b: 1 ′, 2′-d] furan and phenylboronic acid After 0.38 g, 20 ml of toluene and 4.8 ml of 2M potassium carbonate aqueous solution were charged and purged with nitrogen, the mixture was stirred at room temperature for 5 minutes. Thereafter, 27 mg of Pd (PPh ₃ ) ₄ was added and purged with nitrogen, then the temperature was raised to the reflux temperature, and the mixture was stirred at the reflux temperature for 12 hours. The reaction solution was air-cooled, poured into 30 ml of water, and the organic layer was separated. After drying over anhydrous magnesium sulfate and distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 5,9-bis (4-propylphenyl) dinaphtho [2,1-b: 1 ′, 2′- d] 0.42 g of furan was obtained.

(Synthesis of 3P-21DNFU)
In a 50 ml three-necked flask equipped with a thermometer, a condenser, and a magnetic stirrer, 0.5 g of 4,4′-dibromodinaphtho [2,1-b: 1 ′, 2′-d] furan and 4-propyl After 0.72 g of phenylboronic acid iminodiethanol ester, 20 ml of toluene and 4.8 ml of 2M potassium carbonate aqueous solution were charged with nitrogen, the mixture was stirred for 5 minutes at room temperature. Thereafter, 27 mg of Pd (PPh ₃ ) ₄ was added and purged with nitrogen, then the temperature was raised to the reflux temperature, and the mixture was stirred at the reflux temperature for 12 hours. The reaction solution was air-cooled, poured into 30 ml of water, and the organic layer was separated. After drying over anhydrous magnesium sulfate and distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 5,9-bis (4-propylphenyl) dinaphtho [2,1-b: 1 ′, 2′- d] 0.52 g of furan was obtained.

(Synthesis of 5P-21DNFU)
In a 50 ml three-necked flask equipped with a thermometer, a condenser, and a magnetic stirrer, 0.5 g of 4,4′-dibromodinaphtho [2,1-b: 1 ′, 2′-d] furan and 4-pentyl After 0.644 g of phenylboronic acid iminodiethanol ester, 20 ml of toluene and 4.8 ml of 2M potassium carbonate aqueous solution were charged with nitrogen, the mixture was stirred for 5 minutes at room temperature. Thereafter, 27 mg of Pd (PPh ₃ ) ₄ was added and purged with nitrogen, then the temperature was raised to the reflux temperature, and the mixture was stirred at the reflux temperature for 12 hours. The reaction solution was air-cooled, poured into 30 ml of water, and the organic layer was separated. After drying over anhydrous magnesium sulfate and distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 5,9-bis (4-pentylphenyl) dinaphtho [2,1-b: 1 ′, 2′- d] 0.55 g of furan was obtained.
When the content of halogen atoms, palladium atoms, and boron atoms was quantified, fluorine content: <0.1 ppm, chlorine content: 0.4 ppm, bromine content: <0.1 ppm, iodine content: <0.1 ppm The boron content was 0.02 ppm and the palladium content was 0.11 ppm.

(Synthesis of 7P-21DNFU)
In a 50 ml three-necked flask equipped with a thermometer, a condenser tube, and a magnetic stirrer, 0.5 g of 4,4′-dibromodinaphtho [2,1-b: 1 ′, 2′-d] furan and 4-heptyl After 0.90 g of phenylboronic acid iminodiethanol ester, 20 ml of toluene and 4.8 ml of 2M potassium carbonate aqueous solution were charged with nitrogen, the mixture was stirred for 5 minutes at room temperature. Thereafter, 27 mg of Pd (PPh ₃ ) ₄ was added and purged with nitrogen, then the temperature was raised to the reflux temperature, and the mixture was stirred at the reflux temperature for 12 hours. The reaction solution was air-cooled, poured into 30 ml of water, and the organic layer was separated. After drying over anhydrous magnesium sulfate and distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 5,9-bis (4-heptylphenyl) dinaphtho [2,1-b: 1 ′, 2′- d] 0.69 g of furan was obtained.

The synthesis reaction formulas of Example 1 and Example 4 are shown in the following chemical formula [3] and chemical formula [4].
Example 1
Example 4

(Production of single crystal)
P-21DNFU was obtained by a casting method in which a saturated solution was prepared using N, N-dimethylformamide as a solvent and cast on a Si / SiO ₂ substrate. For 3P-21DNFU, 5P-21DNFU, and 7P-21DNFU, a 1 wt% toluene solution was prepared, and single crystals were obtained by a liquid phase method in which ethanol was added as a poor solvent.

(Preparation of P-21DNFU single crystal transistor)
A field effect transistor (FET) was fabricated by applying a carbon paste to a single crystal on a Si / SiO 2 substrate to form source and drain electrodes.
(Production of 3P-21DNFU single crystal transistor)
A toluene solution of polystyrene prepared to 3 wt% was spin-coated at 2000 rpm for 30 seconds, and a 3P-21DNFU single crystal was placed on a Si / SiO ₂ substrate subjected to annealing treatment at 90 ° C. for 1 hour, and a carbon paste was applied. An FET was fabricated by using the source and drain electrodes.
(Fabrication of 5P-21DNFU single crystal transistor)
A toluene solution of polystyrene prepared to 3 wt% was spin-coated at 2000 rpm for 30 seconds, and a 5P-21DNFU single crystal was placed on a Si / SiO ₂ substrate subjected to annealing treatment at 90 ° C. for 1 hour, and a carbon paste was applied, An FET was fabricated by using the source and drain electrodes.
(Production of 7P-21DNFU single crystal transistor)
7P-21DNFU single crystal on a Si / SiO ₂ substrate spin-coated with a solution of CYTOP: thinning solution = 1: 9 at 2000 rpm for 30 seconds and annealed at 90 ° C. for 10 minutes and 200 ° C. for 1 hour. A FET was fabricated by applying carbon paste and forming source and drain electrodes.

(Evaluation of transistor characteristics)
As a representative example, FIGS. 1 and 2 show graphs of output characteristics and transfer characteristics of a 3P-21DNFU single crystal transistor. The field effect mobility was calculated from the transfer characteristic graph. Table 1 shows a summary of the characteristics of each single crystal transistor manufactured in Example 7.

Organic semiconductor devices using organic semiconductors can be fabricated at a lower temperature (300 ° C. or lower) than those using inorganic semiconductors, and high-quality thin films can be formed even on plastic substrates with low heat resistance. In addition to being light and thin, it is possible to produce organic semiconductor devices that can be bent softly and have so-called human affinity. The 21DNFU derivative of the present application shows a remarkable effect on carrier mobility and the like as an organic semiconductor, and future demand is expected.

Claims (5)

A dinaphthofuran compound represented by the following chemical formula [1].
(In the chemical formula [1], Ar ¹ and Ar ² each represent an aryl group or a heterocyclic group, and R ¹ and R ² represent a hydrogen atom and a deuterium atom, a halogen atom, an alkyl group, an alkenyl group, (Selected from alkynyl group, alkoxyl group, carbonyl group, ester group, amide group, imino group, sulfide group, sulfoxide group, sulfonyl group, silyl group, nitro group, nitrile group, and mercapto group.) After dinaphtho [2,1-b: 1 ′, 2′-d] furan is halogenated to 4,4′-dihalodinaphtho [2,1-b: 1 ′, 2′-d] furan, boronic acid or The production method which manufactures the dinaphthofuran compound of Claim 1 via reaction with the derivative etc. The compound of claim 1, wherein the halogen atom content is less than 10 ppm, the palladium atom content is less than 10 ppm, and the boron atom content is 10 ppm or less. The compound according to any one of claims 1 and 3, wherein a compound having a dinaphthofuran skeleton of either R or S is selectively used. An organic transistor manufactured using the dinaphthofuran compound according to claim 1.