WO2011087130A1 - Composé acétylénique et matériau semi-conducteur organique le comportant - Google Patents

Composé acétylénique et matériau semi-conducteur organique le comportant Download PDF

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WO2011087130A1
WO2011087130A1 PCT/JP2011/050749 JP2011050749W WO2011087130A1 WO 2011087130 A1 WO2011087130 A1 WO 2011087130A1 JP 2011050749 W JP2011050749 W JP 2011050749W WO 2011087130 A1 WO2011087130 A1 WO 2011087130A1
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group
compound
mmol
nmr
intermediate compound
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純蔵 大寺
明浩 折田
尚 杉岡
浩一 金平
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株式会社クラレ
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]

Definitions

  • the present invention relates to an acetylene compound that is useful as a semiconductor material exhibiting N-type characteristics of an organic electronic device, and an N-type organic semiconductor material containing the acetylene compound.
  • ⁇ -conjugated organic compounds generally have semiconducting properties and are called organic semiconductors.
  • organic electronic devices such as organic thin film transistors, organic electroluminescence, printable circuits, organic capacitors, and organic solar cells have attracted attention, and much research has been conducted on the development of organic semiconductor materials.
  • Patent Document 1 discloses an aryl group-containing triamine compound useful as a hole transport material or a light emitting material for an organic electroluminescence device and a method for producing the same.
  • Patent Document 2 discloses an organic electroluminescent device containing an aromatic amine compound having a triazine skeleton in a hole transport layer.
  • Organic semiconductor materials are roughly classified into P-type semiconductors related to hole injection or hole transport and N-type semiconductors related to electron injection or electron transport.
  • P-type organic semiconductor materials have been reported regardless of whether they are small molecules or polymers, but N-type organic semiconductor materials are rarely reported.
  • the stronger the electron withdrawing ability the greater the tendency to oxidize, so it has been said that the development of materials having strong N-type organic semiconductor characteristics is relatively difficult compared to P-type materials.
  • N-type organic semiconductors examples include fluorine substitution of ⁇ -conjugated compounds such as pentacenes (Non-Patent Document 1), oligothiophenes (Non-Patent Document 2), and copper phthalocyanine compounds (Non-Patent Document 3), and fullerenes.
  • a derivative nonpatent literature 4 is mentioned.
  • These N-type organic semiconductors, pentacenes, and the like can delocalize ⁇ electrons widely, but by themselves, the movement of electrons in device electrodes and organic semiconductors, and the movement of electrons between organic semiconductors are insufficient. Is.
  • a fullerene derivative is a typical N-type organic semiconductor, but a fullerene skeleton requires a special manufacturing method such as arc discharge or plasma decomposition, and is therefore expensive and difficult to say as an industrially suitable material.
  • proposals for N-type organic semiconductors have been made energetically, but further proposals for new organic semiconductor compounds are indispensable for improving the performance of various devices.
  • Non-Patent Document 5 the present inventors have reported arylene ethynylene derivatives, all of which have the properties of P-type semiconductors and N-type. The compound which shows the property is not known.
  • the present invention has been made in order to solve the above problems, and has a molecular design having planarity and symmetry so that ⁇ electrons can be widely delocalized. It aims at providing the acetylene compound used as the organic-semiconductor material which shows, and the N type organic-semiconductor material containing it.
  • the acetylene compound according to claim 1 made to achieve the above object has the following chemical formula (I):
  • R 1 to R 16 , X 1 and X 2 are the same or different from each other, and are linear, branched and / or cyclic perfluoroalkyl groups having 1 to 20 carbon atoms. Or a fluorine atom, and the remainder is a linear, branched and / or cyclic hydrocarbon group having 1 to 20 carbon atoms or a hydrogen atom which may be the same or different from each other and may have a substituent. It is represented by.
  • the acetylene compound according to claim 2 is the one described in claim 1, wherein X 1 and X 2 are the same or different perfluoroalkyl groups, and R 1 to R 16 are , At least four of which are fluorine atoms.
  • the N-type organic semiconductor material according to claim 3 contains the acetylene compound according to claim 1.
  • the acetylene compound of the present invention has a fluorine atom or a perfluoroalkyl group introduced into a planar arylene ethynylene skeleton, and can be an organic semiconductor material exhibiting strong N-type characteristics.
  • the N-type organic semiconductor material of the present invention can realize efficient electron transfer between a device electrode and an organic semiconductor and smooth electron transfer between organic semiconductor molecules.
  • the acetylene compound of the present invention is represented by the chemical formula (I), and has a fluorine atom or a perfluoroalkyl group introduced into the arylene ethynylene skeleton.
  • this acetylene compound has a molecular design with planarity and symmetry that allows ⁇ electrons to be widely delocalized, and when used as an organic semiconductor material, its lowest unoccupied orbital (LUMO) level and device This shows a good balance with the work function of the electrode.
  • LUMO lowest unoccupied orbital
  • the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R 1 to R 16 , X 1 and X 2 may have a substituent, for example.
  • substituents include an alkyl group, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, and an aryl group which may have a substituent.
  • the alkyl group may be a linear or branched alkyl group or a cyclic alkyl group.
  • the alkyl group may have a substituent.
  • substituents include an aryl group such as a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group; a pyridyl group, a thienyl group, a furyl group, a pyrrolyl group, Heteroaromatic groups such as imidazolyl, pyrazinyl, oxazolyl, thiazolyl, pyrazolyl, benzothiazolyl, benzoimidazolyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy , Alkoxy groups such as tert-butoxy group, pentyloxy group, isopentyloxy group, neopentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, non
  • the alkenyl group may be linear, branched or cyclic.
  • Examples of the alkenyl group include a vinyl group, an allyl group, a methylvinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group.
  • the alkynyl group may be linear or branched.
  • Examples of the alkynyl group include ethynyl group, propynyl group, propargyl group, butynyl group, pentynyl group, hexynyl group, and phenylethynyl group.
  • alkenyl groups and alkynyl groups may have a substituent, and the same substituents as those exemplified for the alkyl group can be used as such substituents.
  • aryl group examples include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. These aryl groups may have a substituent, and as such a substituent, a substituent other than the aryl group exemplified for the alkyl group, the above-described alkyl group, alkenyl group, alkynyl group, and the like can be used.
  • the perfluoroalkyl group represented by R 1 to R 16 , X 1 and X 2 is, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- A butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, isohexyl group, 2-ethylhexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, etc.
  • cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptanyl group, cyclooctanyl group, cyclononanyl group, cyclodecanyl group, cycloundecanyl group, cyclododecanyl group, etc.
  • Straight chain, branched chain or cyclic such as 1 to 20 carbon atoms Of the hydrogen atoms of the kill group, in which 80-100% is substituted with a fluorine atom.
  • the perfluoroalkyl group in the present invention includes a partial fluoroalkyl group in which the fluorine atom is 80% or more and less than 100% of the number of hydrogen atoms of the alkyl group.
  • R 1 to R 16 , X 1 and X 2 are perfluoroalkyl groups or fluorine atoms, and examples thereof include the following compounds (1) to (14). Among these, a perfluoroalkyl group or a group having 8 or more fluorine atoms is more preferable. Further, these R 1 to R 16 , X 1 and X 2 may be the same or different.
  • acetylene compounds can be obtained by a method based on the so-called Sonogashira cross-coupling reaction between the corresponding phenyl halide compound and the phenylacetylene compound, a method of reacting an aromatic fluorine compound with a phenylacetylide compound, or a combination thereof. Can be synthesized by different methods.
  • Z of the terminal alkyne compound to be reacted with the phenyl halide compound is a hydrogen atom or an alkylsilane (—SiR ′ 3 ).
  • the alkylsilane (—SiR ′ 3 ) is preferably such that R ′ is lower alkyl such as methyl or ethyl.
  • the phenylacetylene compound constituting a part of the acetylene compound (I) obtained in the step (A) is desorbed by the action of a base to acetylate (B-1) to obtain a phenylacetylide anion.
  • the desired acetylene compound is synthesized by reacting (B-2) with perfluorodiphenylacetylene, which is an aromatic fluorine compound.
  • the halogen substituent of the phenyl halide compound is an iodine atom
  • the halogen substituent may be a bromine atom or a chlorine atom.
  • the Sonogashira cross-coupling reaction in the step (A) is preferably performed in the presence of a palladium catalyst, a copper catalyst and a base.
  • the acetylation (B-1) is preferably performed in the presence of a solvent and a base. Furthermore, the reaction (B-2) of the phenylacetylene compound that constitutes a part of the acetylene compound and perfluorodiphenylacetylene is preferably carried out in the presence of a solvent.
  • Examples of the base used include, when Z is a hydrogen atom, organolithium compounds such as n-butyllithium, s-butyllithium and t-butyllithium; metal hydrides such as sodium hydride and potassium hydride; Metal hydroxides such as sodium and potassium hydroxide; and Grignard compounds such as methylmagnesium bromide, ethylmagnesium chloride, and phenylmagnesium chloride.
  • organolithium compounds such as n-butyllithium, s-butyllithium and t-butyllithium
  • metal hydrides such as sodium hydride and potassium hydride
  • Metal hydroxides such as sodium and potassium hydroxide
  • Grignard compounds such as methylmagnesium bromide, ethylmagnesium chloride, and phenylmagnesium chloride.
  • Z is alkylsilane (—SiR ′ 3 )
  • the solvent used is preferably a solvent that can be used even in the presence of a base, in which each compound as a raw material is dissolved to such an extent that the reaction rate is not hindered.
  • a solvent include tetrahydrofuran, diethyl ether, n-hexane, cyclohexane, n-heptane and the like.
  • the acetylene compound thus obtained can be isolated and purified by a method usually performed in the isolation and purification of organic compounds.
  • the reaction mixture is separated into an organic layer and an aqueous layer using a separatory funnel, and the aqueous layer is extracted with a solvent such as diethyl ether, ethyl acetate, toluene, methylene chloride, 1,2-dichloroethane, and the extract.
  • the organic layer is combined, dried over anhydrous sodium sulfate, etc., and then concentrated, and the crude product obtained by concentration is purified by sublimation, recrystallization, distillation, silica gel column chromatography, etc.
  • An acetylene compound can be obtained.
  • Examples 1 to 5 show the synthesis of acetylene compounds to which the present invention is applied.
  • Example 1 A chemical reaction formula (III) for obtaining 2,3,4,5,6-pentafluorodiphenylacetylene (a) as an intermediate compound for synthesizing the acetylene compound is shown below.
  • HRMS uses a high performance double-focusing mass spectrometer JEOL-JMS700 (manufactured by JEOL Ltd.), acceleration voltage: 8 kV, ionization method: electron ionization method, ionization energy: 70 eV, detector voltage: 1.5 kV It was measured by. Moreover, it confirmed that it was an error range of 10 ppm or less with respect to the estimated composition of a target object.
  • Example 2 A chemical reaction formula (V) for obtaining trimethylsilylethynylpentafluorobenzene (b) as an intermediate compound for synthesizing the acetylene compound is shown below.
  • TMS is an abbreviation for trimethylsilyl group (—Si (CH 3 ) 3 ).
  • Pd (PPh 3 ) 4 (0.25 mmol, 0.29 g)
  • copper (I) iodide (0.25 mmol, 48 mg
  • pentafluorobromobenzene 5.0 mmol, 1.23 g.
  • phenylacetylene (0.62 mmol, 63 mg) and THF (1 ml) were added, then cooled to ⁇ 78 ° C. and 2.1 equivalents of n-BuLi (1.3757 M in hexane solution). , 0.43 ml) was added and stirred for 30 minutes.
  • a THF (2.0 ml) solution of perfluorodiphenylacetylene (c) (0.28 mmol, 0.10 g) obtained in the above synthesis, and the mixture was warmed to room temperature and stirred for 15 hours.
  • a reactor purged with nitrogen was charged with iodine (1.0 mmol, 0.25 g), tetrafluorobenzotrifluoride (1.0 mmol, 0.22 g), tripotassium phosphate (2.0 mmol, 0.43 g) and THF.
  • the mixture was stirred with heating at 130 ° C. for 2 hours.
  • the reaction solution was cooled, washed once with a saturated aqueous sodium hydrogen sulfite solution (20 ml), the aqueous layer was re-extracted three times with diethyl ether (20 ml), and mixed with the previous organic layer.
  • the reaction mixture was cooled, washed with saturated aqueous ammonium chloride solution (20 ml) three times, and the aqueous layer was extracted three times with ethyl acetate (20 ml).
  • the obtained organic layer was washed with saturated brine (20 ml) and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
  • the obtained residue was purified by silica gel column chromatography (developing solvent: hexane) to obtain a colorless liquid intermediate compound (e) (yield: 197 mg, yield: 86%).
  • perfluorodiphenylacetylene (c) (0.28 mmol, 0.10 g) obtained in Example 2 and 4-trimethylsilylethynyl-2,3,5,6 obtained in the above synthesis were used.
  • -Tetrafluorobenzotrifluoride (e) (0.67 mmol, 0.21 g) and THF (4 ml) were added and cooled to 0 ° C.
  • Tetrabutylammonium fluoride (TBAF) 1.0 M tetrahydrofuran solution, 0.28 mmol, 0.028 ml
  • Example 4 A chemical reaction formula (VI) for obtaining perfluorodiphenylacetylene (c), which is an intermediate compound for synthesizing the acetylene compound, using the intermediate compound (b) obtained in Example 2 is shown below.
  • Perfluorodiphenylacetylene (c) (2.0 mmol, 0.72 g) obtained by the above synthesis was added to a reactor substituted with nitrogen, and dissolved in THF (8 ml). After cooling to 0 ° C. and adding lithium hexamethyldisilazide (LiHMDS) (1.0 M tetrahydrofuran solution, 8.0 mmol, 8.0 ml), the mixture is warmed to room temperature and stirred for 18 hours. After quenching by adding aqueous ammonium chloride, extract three times with ethyl acetate. Concentration under reduced pressure yields an intermediate crude product. The crude product is added to a nitrogen purged reactor and dissolved with THF (5 ml).
  • LiHMDS lithium hexamethyldisilazide
  • Trimethylsilylethynylpentafluorobenzene (b) (3.0 mmol) dissolved in THF was added to a reactor purged with nitrogen, cooled to 0 ° C., and n-butylmagnesium chloride (n-BuMgCl) (2.0 M tetrahydrofuran solution). , 4.5 ml, 9 mmol) was added dropwise. It returned to room temperature and stirred for 15 hours. After completion of stirring, the mixture was cooled to 0 ° C., quenched by adding an aqueous ammonium chloride solution, and washed three times with ethyl acetate.
  • n-BuMgCl n-butylmagnesium chloride
  • a reactor substituted with nitrogen was charged with 1-trimethylsilylethynyl-2,3,5,6-tetrafluoro-4-butylbenzene (j) (1.5 mmol), perfluorodiphenylacetylene (c) (0.5 mmol, 0 .18 g) was added and dissolved in THF (5 ml). After cooling to 0 ° C., TBAF (1.0 M tetrahydrofuran solution, 0.10 ml, 0.10 mmol) was added dropwise and stirred for 18 hours. After stirring, the reaction mixture was quenched with water and extracted three times with dichloromethane. The suspended organic layer was concentrated and dried under reduced pressure.
  • the obtained residue was subjected to gel filtration using a toluene solvent, and then recrystallized and purified using THF as a solvent to obtain the target product (16) as a yellow solid (yield 44%, melting point 215). -217 ° C).
  • the acetylene compound of the present invention is useful as a semiconductor material for organic electronic devices such as field effect transistors, organic electroluminescence, printable circuits, organic capacitors, and organic solar cells, and is used as an organic semiconductor exhibiting N-type characteristics.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention porte sur un composé acétylénique, dont la molécule a été conçue de façon à avoir un caractère plan et symétrique, les électrons π pouvant être largement délocalisés. Le composé acétylénique sert de matériau semi-conducteur organique dans lequel les électrons se déplacent en douceur et qui présente de fortes caractéristiques de type N. L'invention porte également sur un matériau semi-conducteur organique de type N qui comporte le composé acétylénique. Le composé acétylénique est un composé représenté par la formule chimique (I), dans laquelle au moins quatre des substituants R1 à R16, X1 et X2 sont identiques les uns aux autres ou différents les uns des autres et représentent des groupes alkyles perfluorés en C1-20 linéaires, ramifiés et/ou cycliques ou des atomes de fluor et les autres sont identiques les uns aux autres ou différents les uns des autres et représentent des groupes hydrocarbonés en C1-20 linéaires, ramifiés et/ou cycliques ou des atomes d'hydrogène.
PCT/JP2011/050749 2010-01-18 2011-01-18 Composé acétylénique et matériau semi-conducteur organique le comportant WO2011087130A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013544233A (ja) * 2010-10-13 2013-12-12 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波コンポーネントのための前記化合物の使用
US9523037B2 (en) 2011-01-21 2016-12-20 Merck Patent Gmbh Liquid-crystalline media, components for high-frequency technology, and mesogenic compounds

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WO2008156121A1 (fr) * 2007-06-21 2008-12-24 Idemitsu Kosan Co., Ltd. Transistor à couches minces organique et transistor électroluminescent à couches minces organique

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JPH0341458A (ja) * 1989-07-07 1991-02-21 Fuji Photo Film Co Ltd 電子写真感光体
JPH1045642A (ja) * 1996-08-02 1998-02-17 Dainippon Ink & Chem Inc 誘電率異方性の極めて大きい液晶性化合物
JPH1072384A (ja) * 1996-08-28 1998-03-17 Chisso Corp ラテラルハロゲン置換基を有する４環化合物および液晶組成物
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Publication number Priority date Publication date Assignee Title
JP2013544233A (ja) * 2010-10-13 2013-12-12 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体のための化合物および高周波コンポーネントのための前記化合物の使用
US9523037B2 (en) 2011-01-21 2016-12-20 Merck Patent Gmbh Liquid-crystalline media, components for high-frequency technology, and mesogenic compounds
US9752077B2 (en) 2011-01-21 2017-09-05 Merck Patent Gmbh Liquid-crystalline media, components for high-frequency technology, and mesogenic compounds

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