WO2012090972A1 - Composé réactif, et méthode de production d'un polymère utilisant ce composé - Google Patents

Composé réactif, et méthode de production d'un polymère utilisant ce composé Download PDF

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WO2012090972A1
WO2012090972A1 PCT/JP2011/080139 JP2011080139W WO2012090972A1 WO 2012090972 A1 WO2012090972 A1 WO 2012090972A1 JP 2011080139 W JP2011080139 W JP 2011080139W WO 2012090972 A1 WO2012090972 A1 WO 2012090972A1
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健一郎 大家
大西　敏博
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
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    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
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    • C08G2261/124—Copolymers alternating
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1426—Side-chains containing oxygen containing carboxy groups (COOH) and/or -C(=O)O-moieties
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
    • C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/411—Suzuki reactions
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/70—Post-treatment
    • C08G2261/80—Functional group cleavage, e.g. removal of side-chains or protective groups
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/91—Photovoltaic applications
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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    • C08G2261/92—TFT applications
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/94—Applications in sensors, e.g. biosensors
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    • C08G2261/90—Applications
    • C08G2261/95—Use in organic luminescent diodes

Definitions

  • the present invention relates to a reactive compound and a method for producing a polymer compound using the same.
  • the ⁇ -conjugated polymer compound is attracting attention for its absorption of light in the visible light region, its emission characteristics, its conductivity characteristics, and its semiconductor characteristics, and many organic electroluminescence elements, switching elements, photoelectric conversion elements, etc. Application to devices is being studied. In recent years, an element having an organic layer containing a ⁇ -conjugated polymer compound can omit a high-temperature process and a vacuum process necessary for manufacturing an inorganic element such as a silicon-based semiconductor, and can reduce energy in manufacturing. An element having an organic layer containing a ⁇ -conjugated polymer compound can be a flexible film-like element, and has attracted attention as a next-generation element.
  • the organic layer containing a ⁇ -conjugated polymer compound can be produced from a solution in which the ⁇ -conjugated polymer compound is dissolved in a solvent. Since ⁇ -conjugated polymer compounds that do not have substituents are insoluble in many solvents, they have long-chain groups such as long-chain alkyl groups in the side chain, improving solubility in organic solvents. ⁇ -conjugated polymer compounds that have been made are being studied. However, an element including a ⁇ -conjugated polymer compound having a long-chain group in the side chain has a solvent in the solution when the solution is applied on the organic layer containing the ⁇ -conjugated polymer compound to form another layer.
  • the film thickness of the organic layer is difficult to be uniform, and the glass transition temperature of the ⁇ -conjugated polymer compound having a long-chain group in the side chain is low, so it is resistant to heat. It is known that the nature is low.
  • an intermediate compound of a ⁇ -conjugated polymer compound which is formed into a thin film containing the intermediate compound by using a soluble intermediate compound having a group that can be removed by heating or the like, is then removed.
  • a method for producing a ⁇ -conjugated polymer compound by separating them has been proposed.
  • the formula (A) To produce a soluble intermediate compound, and form a thin film containing the intermediate compound from a solution containing the intermediate compound and a solvent, followed by thermal desorption.
  • a method of producing a ⁇ -conjugated polymer compound by reaction and producing a thin film containing the ⁇ -conjugated polymer compound has been proposed (Chemical Communications, 73-74 (1997)).
  • a compound capable of producing a polymer compound has been demanded.
  • the present invention relates to a compound of formula (I)
  • Y ′ represents a divalent group.
  • R 1 and R 2 are the same or different and each represents a substituent.
  • N and m are the same or different and each represents an integer of 0 to 3.
  • a 'and B' are the same or different, if .R 1 representing a boron residue or boric acid ester residue are a plurality, if they have a plurality good .R 2 is also different phases in the same, They may be the same or different.
  • the compound represented by these is provided.
  • the divalent group represented by Y ′ is, for example, a formula (Y-1) to a formula (Y-8).
  • R 3 ⁇ R 13 are the same or different, X 1 .X 1 have a.
  • Plurality representing a halogen atom represents a hydrogen atom or a substituent These may be the same or different.
  • the boric acid ester residue represented by A ′ or B ′ is represented by, for example, formula (AB-1) to formula (AB-8). It is group represented by these.
  • the present invention also relates to a compound represented by formula (I) and formula (II) (In the formula, C ′ represents an optionally substituted arylene group, an optionally substituted heteroarylene group or a divalent aromatic amine residue, provided that C ′ is represented by the formula (III).
  • D is a halogen atom, an alkyl sulfonate group, an aryl sulfonate group or an arylalkyl sulfonate group, and two D may be the same or different.
  • a compound represented by formula (III) In the formula, Y ′, R 1 , R 2 , m and n have the same meaning as described above.
  • a repeating unit represented by formula (IV) In the formula, C ′ represents the same meaning as described above.) The manufacturing method of the high molecular compound containing the repeating unit represented by these is provided.
  • the present invention relates to a compound represented by formula (I) and formula (V) (In the formula, D, Y ′, R 1 , R 2 , m and n represent the same meaning as described above.)
  • the manufacturing method of the high molecular compound containing the repeating unit represented by Formula (III) which polymerizes the compound represented by this is also provided.
  • the present invention also relates to a compound represented by formula (I), a compound represented by formula (II) and formula (VI).
  • a ′, B ′ and C ′ represent the same meaning as described above.
  • a method for producing a polymer compound comprising a repeating unit represented by formula (III) and a repeating unit represented by formula (IV), wherein the compound represented by formula (III) is polymerized.
  • the present invention provides a repeating unit represented by the formula (III) for polymerizing a compound represented by the formula (I), a compound represented by the formula (II), and a compound represented by the formula (V).
  • a compound represented by formula (I), a compound represented by formula (II), a compound represented by formula (V), and a compound represented by formula (VI) are polymerized.
  • a method for producing a polymer compound comprising a repeating unit represented by III) and a repeating unit represented by formula (IV).
  • Y ′ represents a divalent group.
  • the divalent group is preferably a group that can be eliminated by applying energy such as heat or light to the compound represented by the formula (I).
  • Examples of the divalent group represented by Y ′ include the following groups.
  • R 3 ⁇ R 13 are the same or different, X 1 .X 1 have a.
  • Plurality representing a halogen atom represents a hydrogen atom or a substituent These may be the same or different.
  • R 3 to R 13 are preferably a hydrogen atom or a group having 1 to 30 carbon atoms.
  • Examples of the substituent represented by R 3 to R 12 include an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, a butyl group, a hexyl group, an octyl group, and a dodecyl group, a methoxy group, an ethoxy group, and a butoxy group.
  • an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 20 carbon atoms is more preferable, an alkyl group having 1 to 12 carbon atoms is further preferable, and an alkyl group having 1 to 6 carbon atoms is particularly preferable.
  • the substituent represented by R 13 include an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, a butyl group, a hexyl group, an octyl group, and a dodecyl group, a methoxy group, an ethoxy group, a butoxy group, and a hexyl group.
  • X 1 represents a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom). Of the halogen atoms, a chlorine atom and a bromine atom are preferable, and a chlorine atom is more preferable.
  • a ′ and B ′ represent a boronic acid residue or a boric acid ester residue.
  • the boronic acid residue means a dihydroxyboryl group
  • the boric acid ester residue means a group obtained by removing one hydroxyl group from a boric acid diester.
  • a ′ and B ′ are, for example, the formula (AB) (In the formula, R 14 and R 15 are the same or different and each represents a hydrogen atom or an alkyl group.
  • R 14 and R 15 may combine to form a cyclic ester structure together with a boron atom and an oxygen atom. Good.) It is group represented by these.
  • the alkyl group represented by R 14 or R 15 may be linear or branched.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 or 2.
  • the cyclic ester structure includes an ethylene glycol ester structure, a 1,3-propanediol ester structure, a pinacol ester structure, 2, 2 -Dimethyl-1,3-propanediol ester structure, 1,1-dimethyl-3-methyl-1,3-propanediol ester structure are preferred, ethylene glycol ester structure, 1,3-propanediol ester structure, pinacol ester structure Is more preferable, and a pinacol ester structure is more preferable.
  • the borate residue may be a group containing an aryl ester structure.
  • formula (AB-1) to formula (AB-8) (In the formula, Me represents a methyl group, and Et represents an ethyl group.) The group represented by these is preferable.
  • Group represented by formula (AB-7) is preferable, group represented by formula (AB-3), group represented by formula (AB-4), and formula (AB-7)
  • the group represented is more preferable, and the group represented by the formula (AB-7) is more preferable.
  • R 1 and R 2 are the same or different and represent a substituent.
  • the substituent is preferably a group having 1 to 30 carbon atoms.
  • substituents include alkyl groups having 1 to 30 carbon atoms such as methyl, ethyl, butyl, hexyl, octyl, dodecyl, methoxy, ethoxy, butoxy, hexyloxy, octyloxy Groups, alkoxy groups having 1 to 30 carbon atoms such as dodecyloxy group, heteroaryl groups such as thienyl group, and aryl groups having 1 to 30 carbon atoms such as phenyl group and naphthyl group.
  • n and m are the same or different and represent an integer of 0 to 3.
  • n and m are preferably 0.
  • the compound represented by the formula (I) can be used as a raw material for the polymer compound.
  • the repeating unit represented by the formula (III) and the repeating unit represented by the formula (IV) can be produced.
  • D represents a halogen atom, an alkyl sulfonate group, an aryl sulfonate group or an aryl alkyl sulfonate group. Two D may be the same or different.
  • halogen atoms represented by D fluorine atom, chlorine atom, bromine atom, iodine atom
  • a chlorine atom, a bromine atom and an iodine atom are preferable
  • a bromine atom and an iodine atom are more preferable
  • a bromine atom is further preferable.
  • alkyl sulfonate group represented by D include a methane sulfonate group, an ethane sulfonate group, and a trifluoromethane sulfonate group.
  • Examples of the aryl sulfonate group represented by D include a benzene sulfonate group and a p-toluene sulfonate group.
  • Examples of the aryl sulfonate group represented by D include a benzyl sulfonate group.
  • C ′ represents an optionally substituted arylene group, an optionally substituted heteroarylene group or a divalent aromatic amine residue.
  • C ′ is different from the group represented by the formula (III).
  • the arylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon.
  • the number of carbon atoms constituting the aromatic ring contained in the arylene group is usually 6 to 60, preferably 6 to 20.
  • Aromatic hydrocarbon includes a compound containing a benzene ring, a compound containing a condensed ring, a compound containing a structure in which two or more of the independent benzene rings or condensed rings are directly bonded, or a group such as vinylene. Also included are compounds containing such structures.
  • the optionally substituted heteroarylene group refers to the remaining atomic group obtained by removing two hydrogen atoms from an aromatic heterocyclic compound.
  • the number of carbon atoms constituting the heterocyclic ring is usually 3 to 60.
  • the heterocyclic compound refers to a compound that includes a carbon atom and a hetero atom such as oxygen, sulfur, nitrogen, phosphorus, boron, and arsenic as elements constituting a ring among organic compounds having a cyclic structure.
  • the substituent of the arylene group is an alkyl group or an alkoxy group, the carbon number is usually 1-20.
  • the divalent aromatic heterocyclic group has a substituent, the substituent is, for example, an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms.
  • Examples of the optionally substituted arylene group include groups represented by Formulas 1 to 41 and Formulas 131 to 135.
  • Examples of the divalent aromatic heterocyclic group include groups represented by formulas 42 to 130 and 136 to 138.
  • R represents a hydrogen atom or a substituent. When there are a plurality of R, they may be the same or different.
  • Examples of the substituent represented by R include methyl groups, ethyl groups, butyl groups, hexyl groups, octyl groups, dodecyl groups and other alkyl groups, methoxy groups, ethoxy groups, butoxy groups, hexyloxy groups, octyloxy groups.
  • alkoxy groups such as dodecyloxy group, aryl groups such as phenyl group and naphthyl group, and heteroaryl groups such as thienyl group.
  • the substituent is an alkyl group or an alkoxy group, the carbon number thereof is preferably 1-20, more preferably 1-14, and even more preferably 6-14.
  • X 2 in Formula 120 and Formula 122 is the same or different and represents ⁇ CH— or a nitrogen atom.
  • the divalent aromatic amine residue is a group obtained by removing one hydrogen atom on two different aromatic rings from an aromatic amine compound in which three aromatic groups are bonded to a nitrogen atom. Examples of the divalent aromatic amine residue include groups represented by Formula 139 and Formula 140.
  • the compound represented by the formula (I) and the compound represented by the formula (V) may be polymerized to produce a polymer compound containing a repeating unit represented by the formula (III).
  • the compound represented by the formula (I), the compound represented by the formula (II) and the compound represented by the formula (VI) are polymerized, and the repeating unit represented by the formula (III) and the formula (IV) You may manufacture the high molecular compound containing the repeating unit represented.
  • a ′, B ′ and C ′ represent the same meaning as described above.
  • the compound represented by the formula (I), the compound represented by the formula (II) and the compound represented by the formula (V) are polymerized, and the repeating unit represented by the formula (III) and the formula (IV) You may manufacture the high molecular compound containing the repeating unit represented.
  • a compound represented by the formula (I), a compound represented by the formula (II), a compound represented by the formula (V), and a compound represented by the formula (VI) are polymerized, and represented by the formula (III).
  • a polymer compound containing the repeating unit and the repeating unit represented by the formula (IV) may be produced.
  • the polymer compound containing the repeating unit represented by formula (III) produced from the compound represented by formula (I) has a total amount of repeating units possessed by the polymer compound.
  • the amount of the repeating unit represented by the formula (III) is preferably 20 to 100, and more preferably 30 to 70.
  • the polymerization reaction may be any reaction as long as the boronic acid residue or boric acid ester residue contained in the compound represented by formula (I) can react. From the viewpoint of ease of synthesis, a polymerization reaction using a Suzuki coupling reaction is preferable.
  • the polymerization reaction using the Suzuki coupling reaction is a reaction in which a monomer is polymerized in the presence of a palladium catalyst and a base.
  • the palladium catalyst used in the Suzuki coupling reaction include a Pd (0) catalyst and a Pd (II) catalyst.
  • Specific examples of the palladium catalyst include palladium [tetrakis (triphenylphosphine)], palladium acetate, and dichlorobis (triphenylphosphine) palladium (II). Ease of reaction (polymerization) operation, reaction (polymerization) rate From this viewpoint, dichlorobis (triphenylphosphine) palladium (II) and palladium acetate are preferable.
  • the addition amount of the palladium catalyst is not particularly limited as long as it is an effective amount as a catalyst, but with respect to a total of 1 mol of the compound represented by the formula (I) and the compound represented by the formula (VI). Usually, it is 0.0001 mol to 0.5 mol, and preferably 0.0003 mol to 0.1 mol.
  • the base used for the Suzuki coupling reaction is an inorganic base, an organic base, an inorganic salt, or the like.
  • the inorganic base include potassium carbonate, sodium carbonate, and barium hydroxide.
  • Examples of the organic base include triethylamine and tributylamine.
  • An example of the inorganic salt is cesium fluoride.
  • the addition amount of the base is usually 0.5 mol to 100 mol, preferably 0.8 mol, relative to 1 mol in total of the compound represented by the formula (I) and the compound represented by the formula (VI). It is 9 to 20 mol, and more preferably 1 to 10 mol.
  • a phosphorus compound may be added as a ligand. Examples of the phosphorus compound include triphenylphosphine, tri (o-tolyl) phosphine, and tri (o-methoxyphenyl) phosphine.
  • the addition amount is usually 0.5 to 100 mol, preferably 0.9 to 20 mol, more preferably 1 mol to 1 mol of the palladium catalyst. 10 moles.
  • the reaction is usually performed in a solvent.
  • the solvent include N, N-dimethylformamide, toluene, dimethoxyethane, and tetrahydrofuran. From the viewpoint of solubility of the polymer compound, toluene and tetrahydrofuran are preferred.
  • the base may be added to the reaction system as an aqueous solution, and the monomer may be reacted in a two-phase solvent of an aqueous phase and an organic phase.
  • an aqueous solution containing the inorganic salt is usually added to the reaction system, and the monomer is reacted in a two-phase solvent.
  • a phase transfer catalyst such as a quaternary ammonium salt may be added to the reaction system as necessary.
  • the temperature of the Suzuki coupling reaction is usually about 50 to 160 ° C., although it depends on the solvent. From the viewpoint of increasing the molecular weight of the polymer compound, 60 to 120 ° C. is preferable. Alternatively, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the time (reaction time) for performing the Suzuki coupling reaction may be the end point when the target degree of polymerization is reached, but is usually about 0.1 to 200 hours, and preferably about 1 to 30 hours.
  • the Suzuki coupling reaction is performed in a reaction system in which the palladium catalyst is not deactivated under an inert atmosphere such as argon gas or nitrogen gas. For example, it is performed in a system sufficiently deaerated with argon gas or nitrogen gas.
  • reaction vessel for example, after the inside of the reaction vessel (reaction system) is sufficiently substituted with nitrogen gas and degassed, the compound represented by the formula (I), the compound represented by the formula (II), dichlorobis (trimethyl) (Phenylphosphine) palladium (II) was charged, the reaction vessel was sufficiently replaced with nitrogen gas, degassed, and then degassed solvent, for example, degassed toluene was added by bubbling with nitrogen gas in advance. Thereafter, a base degassed by bubbling with nitrogen gas in advance, for example, a degassed sodium carbonate aqueous solution, is dropped into the solution, and then heated and heated, for example, at an reflux atmosphere for 8 hours. Polymerize while holding.
  • a base degassed by bubbling with nitrogen gas in advance for example, a degassed sodium carbonate aqueous solution
  • the polymer compound produced from the compound represented by formula (I) has a polystyrene-equivalent number average molecular weight of usually 1 ⁇ 10 3 to 1 ⁇ 10 8 and 2 ⁇ 10 3 to 1 ⁇ 10 7 . Preferably there is.
  • the number average molecular weight in terms of polystyrene is 1 ⁇ 10 3 or more, a tough thin film is easily obtained.
  • the weight average molecular weight in terms of polystyrene is usually 1.1 ⁇ 10 3 to 1.1 ⁇ 10 8 , and preferably 2.2 ⁇ 10 3 to 1.1 ⁇ 10 7 .
  • the synthesized polymer compound has an effect of increasing the molecular weight and an effect of reducing dispersion. Since a polymer compound having a weight average molecular weight of 1.0 ⁇ 10 4 or more and a polymer compound having a dispersion of 2.0 or less can be obtained, the compound represented by the formula (I) It is preferably used as a monomer for the purpose.
  • the polymer compound produced from the compound represented by the formula (I) if a group involved in polymerization remains at the molecular chain terminal, the characteristics of the device using the obtained polymer compound may deteriorate. Therefore, it is preferable that the terminal is protected with a stable group that does not participate in polymerization.
  • the stable group is preferably a group having a conjugated bond continuous with the conjugated structure of the molecular chain main chain.
  • substituents represented by the formula (6) are listed in columns 6 to 10 of USP 582002.
  • the polymer compound containing the repeating unit represented by the formula (III) produced from the compound represented by the formula (I) is divalent represented by Y ′ by applying energy such as heat and light.
  • the group can be eliminated to produce an anthracene skeleton.
  • any temperature can be set as long as it is not lower than the temperature at which the divalent group represented by Y ′ is eliminated and not higher than the temperature at which the polymer compound is decomposed.
  • it is 150 to 400 ° C, preferably 200 to 350 ° C.
  • the heat treatment time can be selected within an industrial range, but is usually 1 minute to 50 hours, and preferably 10 minutes to 24 hours.
  • the atmosphere for the heat treatment is preferably an inert atmosphere, and examples of the inert atmosphere include a nitrogen gas atmosphere, an argon gas atmosphere, and a vacuum.
  • oxygen is contained in the inert atmosphere, the oxygen concentration is preferably 100 ppm or less, and more preferably 10 ppm or less.
  • the inert atmosphere is a vacuum, the oxygen partial pressure is preferably 200 Pa or less, more preferably 50 Pa.
  • Examples of a method for removing the divalent group represented by Y ′ by light include a method of irradiating ultraviolet rays having a wavelength of 400 nm or less.
  • the light intensity is not particularly limited as long as the divalent group represented by Y ′ can be eliminated.
  • the atmosphere in the case of irradiation with light is also preferably an inert atmosphere, and the range exemplified above can be suitably used.
  • a polymer compound containing a repeating unit represented by the formula (III) is used for an active layer of an organic element, generally, a thin film containing the polymer compound is formed, and energy such as heat and light is formed on the thin film.
  • energy such as heat and light
  • the thin film may be produced by any method, for example, a film formation from a solution containing a polymer compound containing a repeating unit represented by the formula (III), or a film formation method by a vacuum deposition method. It is done.
  • the solvent used for film formation from the solution may be any solvent that dissolves the polymer compound containing the repeating unit represented by the formula (III).
  • the solvent examples include hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, Examples thereof include halogenated hydrocarbon solvents such as bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, chlorobenzene, dichlorobenzene, and trichlorobenzene, and ether solvents such as tetrahydrofuran and tetrahydropyran.
  • hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicycl
  • the polymer compound can usually be dissolved in the solvent in an amount of 0.1% by weight or more.
  • Examples of the method for forming a film from a solution include a method of applying a solution containing a polymer compound containing a repeating unit represented by the formula (III) on a substrate.
  • An organic thin film obtained by forming a thin film containing a polymer compound containing a repeating unit represented by the formula (III) and then eliminating the divalent group represented by Y ′ is suitable for various devices. Can be used. Since the organic thin film described above has high carrier (electron or hole) transport properties, carriers injected from an electrode provided in the organic thin film or charges generated by light absorption can be transported.
  • the above-described organic thin film can be applied to various organic thin film elements such as an organic thin film transistor, an organic thin film solar cell, and an optical sensor by utilizing these characteristics. Hereinafter, these organic thin film elements will be described individually.
  • the organic thin film solar cell including the organic thin film has a pair of electrodes and an active layer made of the organic thin film between the electrodes.
  • At least one of the pair of electrodes is a transparent or translucent electrode.
  • a photovoltaic force is generated between the electrodes, and the organic thin film solar cell is operated.
  • It can also be used as an organic thin film solar cell module by integrating a plurality of organic thin film solar cells.
  • the optical sensor including the organic thin film has a pair of electrodes and an active layer made of the organic thin film between the electrodes. At least one of the pair of electrodes is a transparent or translucent electrode.
  • the organic thin film transistor including the organic thin film includes a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between these electrodes, and a gate electrode for controlling the amount of current passing through the current path. It has a configuration. Examples of the organic thin film transistor include a field effect organic thin film transistor and a static induction organic thin film transistor.
  • a field effect organic thin film transistor includes a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, a gate electrode for controlling the amount of current passing through the current path, and an organic semiconductor layer and a gate electrode It is preferable to provide an insulating layer disposed between the two.
  • the source electrode and the drain electrode are preferably provided in contact with the organic semiconductor layer (active layer), and the gate electrode is preferably provided with an insulating layer in contact with the organic semiconductor layer interposed therebetween.
  • the organic semiconductor layer is constituted by the organic thin film.
  • the static induction organic thin film transistor has a source electrode and a drain electrode, an organic semiconductor layer (active layer) serving as a current path between them, and a gate electrode that controls the amount of current passing through the current path. It is preferable to be provided in the organic semiconductor layer.
  • the source electrode, the drain electrode, and the gate electrode provided in the organic semiconductor layer are preferably provided in contact with the organic semiconductor layer.
  • the structure of the gate electrode may be a structure in which a current path flowing from the source electrode to the drain electrode is formed and the amount of current flowing through the current path can be controlled by a voltage applied to the gate electrode. An electrode is mentioned.
  • the organic semiconductor layer is constituted by the organic thin film.
  • NMR measurement The NMR measurement was performed by dissolving the compound in deuterated chloroform and using an NMR apparatus (Varian, INOVA300).
  • NMR apparatus Variable-Specific NMR apparatus
  • Measurement of number average molecular weight and weight average molecular weight Regarding the number average molecular weight and the weight average molecular weight, the number average molecular weight and the weight average molecular weight in terms of polystyrene were determined by gel permeation chromatography (GPC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp).
  • the polymer compound to be measured was dissolved in tetrahydrofuran to a concentration of about 0.5% by weight, and 30 ⁇ L was injected into GPC. Tetrahydrofuran was used as the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
  • Tetrahydrofuran was used as the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
  • two TSKgel SuperHM-H manufactured by Tosoh
  • TSKgel SuperH2000 manufactured by Tosoh
  • a differential refractive index detector (manufactured by Shimadzu Corporation, trade name: RID-10A) was used as the detector.
  • a spectrophotometer for example, JASCO-V670, made by JASCO Corporation
  • the measurable wavelength range was 200 to 1500 nm, and thus measurement was performed in this wavelength range.
  • the absorption spectrum of the substrate used for measurement was measured.
  • a quartz substrate, a glass substrate, or the like was used as the substrate.
  • a solution containing a polymer compound was applied onto the substrate and dried to form a thin film containing the polymer compound. Then, the absorption spectrum of the laminated body of a thin film and a board
  • the compound (C-1) was insoluble in toluene and was not uniform in the reaction system.
  • the oil bath temperature was set to 120 ° C. and the reaction solution was refluxed for 3.5 hours, whereby the Diels-Alder reaction proceeded and the reaction system became a homogeneous solution.
  • 20 mL of methanol was added to the reaction solution 5 times every 30 minutes (total 100 mL), and the mixture was heated to reflux for 3 hours to obtain a monoester body in which the anhydride was opened.
  • 1 g of concentrated sulfuric acid was added to the reaction solution twice every 3 hours and heated to reflux for 6 hours.
  • Example 2 Synthesis of polymer compound 1 In a 200 mL flask in which the gas in the flask was replaced with argon, 287.1 mg of compound (C-3), 229.1 mg of compound (D-1), 10 mL of toluene and methyltrialkylammonium chloride (trade name Aliquat 336 (registered) 60.6 mg (0.15 mmol) was added to obtain a homogeneous solution, and argon bubbling was performed at 25 ° C. for 30 minutes.
  • the organic layer was washed twice with 20 ml of water, twice with 20 mL of a 3 wt% aqueous acetic acid solution and twice with 20 mL of water, and the obtained solution was poured into methanol to precipitate a polymer.
  • the polymer is filtered and dried.
  • the obtained polymer is redissolved in 30 mL of o-dichlorobenzene, passed through an alumina / silica gel column, the obtained solution is poured into methanol to precipitate the polymer, and the polymer is filtered and dried. As a result, 60 mg of the purified polymer compound 1 was obtained.
  • Example 3 Synthesis of polymer compound 2 Polymerization was conducted in the same manner as in Example 2 except that the compound (D-2) was used instead of the compound (D-1) to obtain a polymer compound 2.
  • the molecular weight in terms of polystyrene of the polymer compound 2 measured by GPC was Mw of 94,000 and Mn of 60,000.
  • Example 4 Synthesis of Polymer Compound 3 Polymerization was carried out in the same manner as in Example 2 except that the compound (D-3) was used instead of the compound (D-1) to obtain a polymer compound 3.
  • Reference Example 2 Measurement of absorption wavelength
  • the polymer compound 1 was dissolved in orthodichlorobenzene at a concentration of 2% by weight to prepare a solution. The solution was applied on a glass plate to form a thin film having a thickness of 50 to 100 nm, and the absorption wavelength of the thin film was measured.
  • the glass plate on which the thin film was formed was heat-treated at 250 to 300 ° C. for 1 hour in a nitrogen atmosphere.
  • the absorption spectrum of the thin film on the glass plate after the heat treatment was measured.
  • the spectrum of the absorption wavelength of the polymer compound 1 before the heat treatment had a maximum value at 530 nm
  • the spectrum of the absorption wavelength of the polymer compound 1 after the heat treatment had a maximum value at 580 nm.
  • Reference Example 3 Measurement of absorption wavelength
  • the absorption wavelength of the polymer compound was measured in the same manner as in Reference Example 2, except that polymer compound 2 was used instead of polymer compound 1.
  • the absorption wavelength spectrum of the polymer compound 2 before the heat treatment had a maximum value at 525 nm, and the absorption wavelength spectrum of the polymer compound 2 after the heat treatment had a maximum value at 550 nm.
  • Reference Example 4 Measurement of absorption wavelength
  • the absorption wavelength of the polymer compound was measured in the same manner as in Reference Example 2, except that polymer compound 3 was used instead of polymer compound 1.
  • the absorption wavelength spectrum of the polymer compound 3 before the heat treatment had a maximum value at 440 nm, and the absorption wavelength spectrum of the polymer compound 3 after the heat treatment had a maximum value at 570 nm.
  • Reference Example 5 Preparation of organic thin film transistor
  • a highly doped n-type silicon substrate having a 300 nm thick thermal oxide film was ultrasonically cleaned in acetone for 10 minutes and then irradiated with ozone UV for 20 minutes. Thereafter, the surface of the thermal oxide film was subjected to silane treatment by spin-coating ⁇ -phenethyltrichlorosilane diluted at a rate of 5 drops (dropped after being collected with a syringe) into 10 ml of toluene.
  • the polymer compound 1 was dissolved in orthodichlorobenzene to prepare a solution having a concentration of the polymer compound 1 of 0.5% by weight, and the solution was filtered through a membrane filter to prepare a coating solution.
  • the coating solution was applied onto the surface-treated substrate by a spin coating method to form a coating film of polymer compound 1.
  • the thickness of the coating film was about 30 nm.
  • the coating film is subjected to a heat treatment at 250 to 300 ° C. for 1 hour in a nitrogen atmosphere, whereby the formula (VII) in the polymer compound 1 is obtained.
  • the field effect mobility ⁇ of carriers in the organic transistor is expressed by the following formula (a) that represents the drain current Id in the saturation region of the electrical characteristics of the organic transistor.
  • Id (W / 2L) ⁇ Ci (Vg ⁇ Vt) 2 (a)
  • L represents the channel length of the organic transistor
  • W represents the channel width of the organic transistor
  • Ci represents the capacitance per unit area of the gate insulating film
  • Vg represents the gate voltage
  • Vt represents the threshold voltage of the gate voltage.
  • Reference Example 7 (Production and Evaluation of Organic Thin Film Transistor) A transistor element was produced in the same manner as in Reference Example 5 except that the polymer compound 2 was used in place of the polymer compound 1, and the transistor characteristics were evaluated in the same manner as in Reference Example 6. The carrier mobility was 7.2 ⁇ 10 ⁇ 4 cm 2 / Vs, and the on / off current ratio was 10 5 . The results are shown in Table 1.
  • Reference Example 8 (Production and Evaluation of Organic Thin Film Transistor) Except that the polymer compound 3 was used in place of the polymer compound 1, a transistor element was produced in the same manner as in Reference Example 5, and the transistor characteristics were evaluated in the same manner as in Reference Example 6.
  • the carrier mobility was 1.8 ⁇ 10 ⁇ 2 cm 2 / Vs, and the on / off current ratio was 10 6 .
  • the results are shown in Table 1.
  • Reference Example 9 (Production and Evaluation of Organic Thin Film Solar Cell) A glass substrate provided with an ITO film with a thickness of 150 nm by a sputtering method was subjected to surface treatment by ozone UV treatment. Next, when the polymer compound 1 and fullerene C60PCBM (phenyl C61-butyric acid methyl ester) (phenyl C61-butyric acid methyl ester, manufactured by Frontier Carbon Co., Ltd.), the ratio of the weight of C60PCBM to the weight of the polymer compound 1 is 3.
  • Ink 1 was produced by dissolving in orthodichlorobenzene as described above.
  • the total weight of polymer compound 1 and C60PCBM was 2.0% by weight with respect to the weight of ink 1.
  • the ink 1 was applied on a glass substrate by spin coating to produce an organic film containing the polymer compound 1.
  • the film thickness was about 100 nm.
  • lithium fluoride was vapor-deposited with a thickness of 2 nm on the organic film by a vacuum vapor deposition machine, and then Al was vapor-deposited with a thickness of 100 nm to produce an organic thin film solar cell.
  • the shape of the obtained organic thin film solar cell was a square of 2 mm ⁇ 2 mm.
  • the obtained organic thin film solar cell is irradiated with a certain amount of light using a solar simulator (trade name OTENTO-SUN II: AM1.5G filter, irradiance 100 mW / cm 2 , manufactured by Spectrometer Co., Ltd.).
  • the photoelectric conversion efficiency, short-circuit current density, open-circuit voltage, and fill factor were determined by measurement. Jsc (short circuit current density) is 0.30 mA / cm 2 , Voc (open circuit voltage) is 0.96 V, ff (fill factor) is 0.30, and photoelectric conversion efficiency ( ⁇ ) was 0.086%.
  • Table 2 The results are shown in Table 2.
  • Reference Example 10 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was prepared and evaluated in the same manner as in Reference Example 9 except that the polymer compound 2 was used instead of the polymer compound 1. Jsc (short circuit current density) is 0.39 mA / cm 2 , Voc (open end voltage) is 0.73 V, ff (fill factor) is 0.24, and photoelectric conversion efficiency ( ⁇ ) was 0.068%. The results are shown in Table 2.
  • Reference Example 11 (Production and Evaluation of Organic Thin Film Solar Cell) An ink and an organic thin film solar cell were prepared and evaluated in the same manner as in Reference Example 9 except that the polymer compound 3 was used instead of the polymer compound 1.
  • the compound of the present invention can be used to produce various polymer compounds containing an anthracenediyl group by a Suzuki coupling reaction.

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  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention concerne un composé de formule (I) pouvant être utilisé dans la production d'une variété de polymères contenant un groupe anthracènediyl, au moyen d'une réaction de couplage de Suzuki. Dans ladite formule, Y' représente un groupe divalent; R1 et R2 sont identiques ou différents et représentent un groupe substituant; n et m sont identiques ou différents et représentent un nombre entier compris entre 0 et 3; A' et B' sont identiques ou différents et représentent un résidu d'acide boronique ou un résidu d'ester borique; R1, lorsqu'il en existe plusieurs qui sont identiques, peuvent être identiques ou différents; et R2, lorsqu'il en existe plusieurs qui sont identiques, peuvent être identiques ou différents.
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