WO2019208516A1 - Composé de cristaux liquides polymérisable, composition de cristaux liquides polymérisable, polymère, film optique, corps optiquement anisotrope, plaque de polarisation, dispositif d'affichage et film antireflet - Google Patents

Composé de cristaux liquides polymérisable, composition de cristaux liquides polymérisable, polymère, film optique, corps optiquement anisotrope, plaque de polarisation, dispositif d'affichage et film antireflet Download PDF

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WO2019208516A1
WO2019208516A1 PCT/JP2019/017082 JP2019017082W WO2019208516A1 WO 2019208516 A1 WO2019208516 A1 WO 2019208516A1 JP 2019017082 W JP2019017082 W JP 2019017082W WO 2019208516 A1 WO2019208516 A1 WO 2019208516A1
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group
carbon atoms
liquid crystal
ring
substituent
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Japanese (ja)
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坂本　圭
久美 奥山
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日本ゼオン株式会社
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Priority to JP2020516352A priority Critical patent/JP7484709B2/ja
Priority to CN201980026401.5A priority patent/CN111989317B/zh
Priority to KR1020207030013A priority patent/KR20210004998A/ko
Publication of WO2019208516A1 publication Critical patent/WO2019208516A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/38—Esters containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present invention relates to a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersion, i.e., reverse wavelength dispersion, exhibiting broadband properties, and exhibiting liquid crystallinity alone. is there.
  • the present invention also relates to a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
  • the present invention also relates to a polymer obtained by polymerizing the polymerizable liquid crystal compound.
  • the present invention relates to an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body.
  • “showing liquid crystallinity” means “having a liquid crystal phase”. Specific examples of the liquid crystal phase include a nematic phase and a smectic phase.
  • a retardation plate used in various devices such as a flat panel display device includes a 1 ⁇ 4 wavelength plate that converts linearly polarized light into circularly polarized light, a 1 ⁇ 2 wavelength plate that converts a polarization vibration plane of linearly polarized light by 90 degrees, and the like. There is. These retardation plates can accurately give a phase difference of 1 / 4 ⁇ or 1 / 2 ⁇ of a light wavelength to a specific monochromatic light. However, the conventional retardation plate has a problem that polarized light output through the retardation plate is converted into colored polarized light.
  • the material constituting the retardation plate has wavelength dispersion with respect to the retardation, and distribution occurs in the polarization state of each wavelength with respect to white light that is a composite wave in which rays in the visible light range are mixed. This is because it is impossible to adjust the input light to polarization having a phase difference of 1 ⁇ 4 ⁇ or 1 ⁇ 2 ⁇ in all wavelength regions.
  • various studies have been made on a broadband retardation plate capable of giving a uniform retardation to light in a wide wavelength range, that is, a so-called reverse wavelength dispersion plate.
  • the present invention has been made in view of the above circumstances, and can form an ideal wavelength dispersion exhibiting broadband properties, that is, an optical film and an optical anisotropic body having reverse wavelength dispersion, and can be used alone.
  • An object of the present invention is to provide a polymerizable liquid crystal compound exhibiting liquid crystallinity.
  • Another object of the present invention is to provide a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
  • Another object of the present invention is to provide a polymer obtained by polymerizing the polymerizable liquid crystal compound.
  • the present invention provides an optical film and an optical anisotropic body prepared using the polymerizable liquid crystal compound, and a polarizing plate, a display device and an antireflection film using the optical anisotropic body. Objective.
  • the present inventors have found that when a predetermined polymerizable liquid crystal compound represented by the following formula (I) is used, an ideal wavelength dispersion exhibiting broadband properties, that is, a reverse wavelength. It has been found that an optical film and an optical anisotropic body having dispersibility can be formed, and that the polymerizable liquid crystal compound exhibits liquid crystallinity alone, and the present invention has been completed.
  • the following polymerizable liquid crystal compound, polymerizable liquid crystal composition, polymer, optical film, optical anisotropic body, polarizing plate, display device, and antireflection film are provided.
  • Ar is represented by any of the following formulas (II-1) to (II-3), and may have one or more substituents other than D.
  • Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms
  • Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent
  • Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Az excludes the case of C (Ay) Ax.
  • * represents a position bonded with Z 1 or Z 2.
  • a 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent.
  • the chain aliphatic group includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, — NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — may be present.
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other.
  • B 1 and B 2 each independently represent a cyclic aliphatic group which may have a substituent or an aromatic group which may have a substituent.
  • R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms.
  • the above is an organic group of any of the groups substituted with —O— or —C ( ⁇ O) —.
  • a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
  • the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C ( ⁇ O) —.
  • P 1 and P 2 each independently represent a polymerizable group. p and q each independently represents an integer of 0 to 2. ]
  • a polymerizable composition comprising the polymerizable liquid crystal compound according to [1].
  • a polarizing plate including the optical anisotropic body according to [5] and a polarizing film.
  • a display device comprising the polarizing plate according to [6].
  • a polymerizable liquid crystal compound capable of forming an optical film and an optical anisotropic body having ideal wavelength dispersibility exhibiting broadband properties, that is, reverse wavelength dispersibility, and exhibiting liquid crystallinity alone.
  • the polymeric liquid crystal composition containing the said polymeric liquid crystal compound is provided.
  • polymerizing the said polymeric liquid crystal compound is provided.
  • the “alkyl group” means a chain (straight chain or branched) saturated hydrocarbon group, and the “alkyl group” means a “cyclo saturated hydrocarbon group” "Alkyl group” is not included.
  • the polymerizable liquid crystal compound and the polymerizable liquid crystal composition of the present invention are not particularly limited, and can be used, for example, when preparing the polymer of the present invention.
  • the polymer of the present invention is not particularly limited, and can be used, for example, as a constituent material of the optical film of the present invention and a constituent material of the layer of the optical anisotropic body of the present invention.
  • the optical anisotropic body of this invention is not specifically limited, For example, it can use for preparation of the polarizing plate of this invention.
  • the polarizing plate of this invention is not specifically limited, For example, it can be used for preparation of the display apparatus and antireflection film of this invention.
  • the intermediate body (compound) of the polymeric liquid crystal compound of this invention is not specifically limited, For example, it can be used when preparing the polymeric liquid crystal compound of this invention.
  • polymerizable liquid crystal compound of the present invention is a compound represented by the following formula (I) (hereinafter sometimes referred to as "polymerizable liquid crystal compound (I)"), and a polymer described later. It can be advantageously used in preparing an optical film and an optical anisotropic body.
  • Ar is represented by any of the following formulas (II-1) to (II-3) and may have one or more substituents other than D.
  • the total number of ⁇ electrons contained in the ring structure in Ar is preferably 10 or more, more preferably 12 or more, preferably 60 or less, preferably 48 or less, and 36 or less. It is particularly preferred.
  • “the total number of ⁇ electrons contained in the ring structure in Ar” is the number of ⁇ electrons contained in one ring structure when the number of ring structures contained in Ar is one. This means that when Ar includes a plurality of ring structures, it means the total number of ⁇ electrons of the plurality of ring structures.
  • * represents bonding to Z 1 or Z 2
  • “-” extending from the inside of the ring represents a bonding hand extending from any position of the ring. To express.
  • Examples of the substituent other than D include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms in which one or more hydrogen atoms are substituted with a halogen atom such as a fluorine atom.
  • Alkyl group N-alkylamino group having 1 to 6 carbon atoms, N, N-dialkylamino group having 2 to 12 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, carboxyl Group, a thioalkyl group having 1 to 6 carbon atoms, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, and the like.
  • -Q- Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • -Ay- Ay represents a hydrogen atom or an organic group having 1 to 30 carbon atoms which may have a substituent.
  • the organic group having 1 to 30 which may have a substituent of Ay include an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms which may have a substituent.
  • At least one of —CH 2 — contained is substituted with —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, or —C ( ⁇ O) —.
  • An alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms which may have a substituent, and an aromatic carbon atom having 6 to 30 carbon atoms which may have a substituent hydrocarbon ring group, aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent, -Gy-Yy-Fy, -SO 2 R a -C ( O) -R b, or, -CS-NH-R b, and the like.
  • the alkyl group having 1 to 20 carbon atoms which may have a substituent, and at least one of —CH 2 — contained in the alkyl group having 1 to 20 carbon atoms is —O—, —S—, A group substituted with —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, or —C ( ⁇ O) — (provided that two or more of —O— or —S— are adjacent to each other).
  • alkyl group having 1 to 20 carbon atoms which may have a substituent include, for example, methyl group, ethyl group, n-propyl group, isopropyl Group, n-butyl group, isobutyl group, 1-methylpentyl group, 1-ethylpentyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl Group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n
  • methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group Is preferred.
  • the “optionally substituted alkyl group having 1 to 20 carbon atoms” preferably has 1 to 12 carbon atoms, and more preferably 4 to 10 carbon atoms.
  • substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; carbon such as dimethylamino group N, N-dialkylamino group having 2 to 12 carbon atoms; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy C1-C12 alkoxy groups substituted with C1-C12 alkoxy groups such as nitro groups; nitro groups; aromatics having 6-18 carbon atoms such as phenyl groups, 1-naphthyl groups, 2-naphthyl groups, etc.
  • Hydrocarbon ring group carbon such as triazolyl group, pyrrolyl group, furanyl group, thiophenyl group (thienyl group), thiazolyl group, benzothiazol-2-ylthio group, etc.
  • a cyclic group, an aromatic heterocyclic group having 2 to 18 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyloxy group having 3 to 8 carbon atoms, a cyclic ether group having 2 to 12 carbon atoms, and 6 to 6 carbon atoms 14 aryloxy groups are preferred, fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group Group,
  • R a is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, which may have a substituent.
  • 18 represents an aromatic hydrocarbon ring group
  • R b is an optionally substituted alkyl group having 1 to 20 carbon atoms and an optionally substituted alkenyl group having 2 to 20 carbon atoms.
  • the number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkenyl group having 2 to 20 carbon atoms which may have a substituent include, for example, a vinyl group, a propenyl group, an isopropenyl group, and a butenyl group.
  • Isobutenyl group pentenyl group, hexenyl group, heptenyl group, octenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonacenyl group, etc. Is mentioned.
  • a vinyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a decenyl group, an undecenyl group, and a dodecenyl group are preferable.
  • the “optionally substituted alkenyl group having 2 to 20 carbon atoms” preferably has 2 to 12 carbon atoms.
  • substituents in the above “optionally substituted alkenyl group having 2 to 20 carbon atoms” include the substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
  • the number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkynyl group having 2 to 20 carbon atoms which may have a substituent include, for example, ethynyl group, propynyl group, 2-propynyl group ( Propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2-octynyl group, nonanyl group, decanyl group, 7-decanyl group, and the like.
  • 2-propynyl group (propargyl group), butynyl group, 2-butynyl group, 3-butynyl group, pentynyl group, 2-pentynyl group, hexynyl group, 5-hexynyl group, heptynyl group, octynyl group, 2- An octynyl group, a nonanyl group, and a decanyl group are preferred.
  • substituents in the above “optionally substituted alkynyl group having 2 to 20 carbon atoms” include substitution in the above “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific example of the group.
  • the number of substituents in the “optionally substituted alkynyl group having 2 to 20 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • C3-C12 cycloalkyl group optionally having substituent Specific examples of the “cycloalkyl group having 3 to 12 carbon atoms” in the “cycloalkyl group having 3 to 12 carbon atoms which may have a substituent” include, for example, a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group. Cyclohexyl group, cyclooctyl group, and the like. Among these, a cyclopentyl group and a cyclohexyl group are preferable.
  • substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” include the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. The same as the specific examples of the substituent.
  • the number of substituents in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • Aromamatic hydrocarbon ring group having 6 to 30 carbon atoms which may have a substituent include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group and the like can be mentioned. Among these, a phenyl group is preferable.
  • substituent in the “optionally substituted aromatic hydrocarbon ring group having 6 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group
  • halogen atoms such as fluorine atom and chlorine atom
  • cyano group such as an ethyl group or a propyl group
  • an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group
  • one or more hydrogen atoms such as a trifluoromethyl group being a fluorine atom or the like
  • a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, and a nitro group are preferable.
  • R a and R b each have the same meaning as described above.
  • the number of substituents in the “aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent
  • aromatic heterocyclic group having 2 to 30 carbon atoms include, for example, a 1-benzofuranyl group, 2-benzofuranyl group, imidazolyl group, indolyl group, furazanyl group, oxazolyl group, quinolyl group, thiadiazolyl group, thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group , Thienyl group, triazinyl group, triazolyl group, naphthyridinyl group, pyrazinyl group, pyrazolyl group, pyranyl group, pyridyl group, pyridazinyl group
  • “monocyclic aromatic heterocyclic groups” such as furanyl group, pyranyl group, thienyl group, oxazolyl group, furazanyl group, thiazolyl group, thiadiazolyl group; benzothiazolyl group, benzoxazolyl group, quinolyl group, 1 -Benzofuranyl group, 2-benzofuranyl group, phthalimide group, benzo [c] thienyl group, benzo [b] thienyl group, thiazolopyridyl group, thiazolopyrazinyl group, benzoisoxazolyl group, benzooxadiazolyl group And "a condensed ring aromatic heterocyclic group” such as a benzothiadiazolyl group;
  • substituent in the “optionally substituted aromatic heterocyclic group having 2 to 30 carbon atoms” include the above “optionally substituted aromatic group having 6 to 30 carbon atoms”.
  • substituent in the “hydrocarbon ring group” are the same.
  • the number of substituents in the “aromatic heterocyclic group having 2 to 30 carbon atoms which may have a substituent” may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • R a may have an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms as a substituent.
  • Specific examples of the “alkyl group having 1 to 6 carbon atoms” include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and the like. Among these, a methyl group and an ethyl group are preferable.
  • C 1-6 alkoxy group examples include, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, Examples thereof include an n-pentyloxy group and an n-hexyloxy group.
  • aromatic hydrocarbon ring group having 6 to 18 carbon atoms examples include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group and the like. Among these, a phenyl group is preferable.
  • R a are preferably a phenyl group and a tolyl group.
  • R b has an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms, and a substituent as described above. It represents an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms which may have a substituent include, for example, a methyl group, an ethyl group, n- Propyl, isopropyl, n-butyl, isobutyl, 1-methylpentyl, 1-ethylpentyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-to Xyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl
  • substituent in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; dimethylamino group An N, N-dialkylamino group having 2 to 12 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group, etc., an alkoxy group having 1 to 20 carbon atoms; methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group An alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms such as ethoxyethoxy group; a nitro group; a carbon group having 6 to 18 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group, etc.
  • An aromatic hydrocarbon ring group of 2 to 1 carbon atoms such as triazolyl group, pyrrolyl group, furanyl group, thienyl group, thiazolyl group, benzothiazol-2-ylthio group
  • fluorine atom, cyano group, methoxy group, ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, phenyl group, 1-naphthyl group, 2-naphthyl group, benzothiazole A -2-ylthio group is preferred.
  • the number of substituents in the “optionally substituted alkyl group having 1 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • alkenyl group having 2 to 20 carbon atoms which may have a substituent as R b
  • Specific examples of “an alkynyl group having 2 to 20 carbon atoms” in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b include “an alkynyl group having 2 to 20 carbon atoms” in the above Ay.
  • Specific examples of the “group” are the same, and preferable examples thereof are also the same as the preferable examples of the “alkynyl group having 2 to 20 carbon atoms” in Ay.
  • substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b are the above-described “optionally substituted alkyl group having 1 to 20 carbon atoms”. Are the same as the specific examples of the substituents.
  • the number of substituents in the “optionally substituted alkenyl group having 2 to 20 carbon atoms” as R b may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • substituent in the “optionally substituted cycloalkyl group having 3 to 12 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom or a chlorine atom; a cyano group; An N, N-dialkylamino group having 2 to 12 carbon atoms such as a group; an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; A nitro group; an aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a phenyl group, a 1-naphthyl group and a 2-naphthyl group; Among these, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; carbon number 1 such as methoxy group, ethoxy group
  • aromatic hydrocarbon ring group having 6 to 18 carbon atoms in the “optionally substituted aromatic hydrocarbon ring group having 6 to 18 carbon atoms” as R b include, for example, phenyl Group, 1-naphthyl group, 2-naphthyl group, and the like. Among these, a phenyl group is preferable.
  • substituent in the “optionally substituted aromatic hydrocarbon ring having 6 to 18 carbon atoms” as R b include, for example, a halogen atom such as a fluorine atom and a chlorine atom; a cyano group; C 2-12 N, N-dialkylamino group such as dimethylamino group; C 1-20 alkoxy group such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group, methoxyethoxy group, etc.
  • An aromatic heterocycle having 2 to 18 carbon atoms such as a nitro group; a triazolyl group, a pyrrolyl group, a furanyl group, or a thiophenyl group, which is substituted with an alkoxy group having 1 to 12 carbon atoms;
  • --Gy-- Gy is (i) an optionally substituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, and (ii) an optionally substituted substituent having 3 to 30 carbon atoms. At least one of —CH 2 — contained in the divalent aliphatic hydrocarbon group is —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O. Substituted with —C ( ⁇ O) —O—, —NR 21 —C ( ⁇ O) —, —C ( ⁇ O) —NR 21 —, —NR 21 —, or —C ( ⁇ O) — An organic group of any of the groups.
  • R 21 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • the “divalent aliphatic hydrocarbon group” is preferably a divalent chain aliphatic hydrocarbon group, and more preferably an alkylene group.
  • substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy include, for example, a halogen atom such as a fluorine atom or a chlorine atom.
  • Atom cyano group; N, N-dialkylamino group having 2 to 12 carbon atoms such as dimethylamino group; alkoxy group having 1 to 20 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, butoxy group; methoxymethoxy group , A methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, or the like, an alkoxy group having 1 to 12 carbon atoms substituted by an alkoxy group having 1 to 12 carbon atoms; a nitro group; a trifluoromethyl group, a pentafluoroethyl group, CH And an alkyl group having 1 to 12 carbon atoms in which one or more hydrogen atoms such as 2 CF 3 are substituted with a fluorine atom; a hydroxyl group and the like.
  • a fluorine atom, a cyano group, an alkoxy group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 12 carbon atoms substituted with an alkoxy group having 1 to 12 carbon atoms are preferable, and a fluorine atom, a cyano group, and a methoxy group are preferable.
  • Ethoxy group, butoxy group, methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, and ethoxyethoxy group are more preferable.
  • the number of substituents in “(i) a divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms which may have a substituent” as Gy may be one or plural. When it has a plurality of substituents, they may be the same as or different from each other.
  • --Yy--- Yy represents —O—, —C ( ⁇ O) —, —S—, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —, —O—C ( ⁇ O) —O—. , —C ( ⁇ O) —S—, —SC— ( ⁇ O) —, —NR 22 —C ( ⁇ O) —, —C ( ⁇ O) —NR 22 —, —O—C ( ⁇ O ) —NR 22 —, —NR 22 —C ( ⁇ O) —O—, —N ⁇ N—, or —C ⁇ C—.
  • R 22 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • —O—, —O—C ( ⁇ O) —O—, —O—C ( ⁇ O) —, and —C ( ⁇ O) —O— are preferable.
  • --Fy-- Fy represents an organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • the number of carbon atoms of the organic group is preferably 2 or more and 30 or less, more preferably 7 or more and 30 or less, still more preferably 8 or more and 30 or less, and particularly preferably 10 or more and 30 or less. preferable.
  • the “carbon number” of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” of Fy is the carbon of the “organic group having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” itself. Means number and does not include carbon atoms of substituents.
  • Fy is (i) “substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms, wherein at least one hydrogen atom has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, And an alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group, or (ii) a substituent having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. It is preferably a cyclic group having 2 to 30 carbon atoms which may have When Fy has a plurality of aromatic hydrocarbon rings and / or a plurality of aromatic heterocycles, each may be the same or different.
  • aromatic hydrocarbon ring in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. And an aromatic hydrocarbon ring having 6 to 30 carbon atoms, such as a fluorene ring.
  • aromatic heterocycle in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, 1H-isoindole-1,3 (2H) -dione ring, 1-benzofuran ring, 2-benzofuran ring, acridine ring, isoquinoline ring, imidazole ring, indole ring, oxadiazole ring, oxazole ring, oxazolopyrazine ring, oxazolopyridine ring, oxazolopyridazine ring, oxazolopyrimidine ring, Quinazoline ring, quinoxaline ring, quinoline ring, cinnoline ring, thiadiazole ring, thiazole ring, thiazolopyrazine ring, thiazolopyridine ring, thiazolopyridazine ring, thiazolopyrimidine ring, thioph
  • substituent in the “optionally substituted cyclic group having 2 to 30 carbon atoms” include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; methyl group, ethyl group, An alkyl group having 1 to 6 carbon atoms such as a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one or more hydrogen atoms such as a trifluoromethyl group or a pentafluoroethyl group are fluorine atoms, etc.
  • R b represents the same meaning as described above, and preferred examples thereof are also the same as described above.
  • Fy may have a plurality of substituents selected from the above-described substituents. When Fy has a plurality of substituents, the substituents may be the same or different.
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • Specific examples of the “alkyl group having 1 to 18 carbon atoms” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include, for example, a methyl group, an ethyl group, A propyl group, an isopropyl group, etc. are mentioned.
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • at least one of the aromatic hydrocarbon ring and the aromatic heterocyclic ring” in the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” means “having 1 to 18 carbon atoms”. It may be directly bonded to the carbon atom of the alkyl group, or —S—, —O—, —C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O).
  • R 23 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • examples of the optionally substituted cyclic group having 2 to 30 carbon atoms having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring include “aromatic groups such as a fluorenyl group and a benzothiazolyl group”.
  • Also included are “a group consisting of an optionally substituted aromatic hydrocarbon ring” and “a group consisting of an optionally substituted aromatic heterocycle having a linking group”.
  • aromatic hydrocarbon ring group in the “optionally substituted aromatic hydrocarbon ring group” include carbon such as phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group and the like. And an aromatic hydrocarbon ring group of 6 to 30;
  • substituent in the “optionally substituted aromatic hydrocarbon ring group” include specific examples of the substituent in the above “optionally substituted cyclic group having 2 to 30 carbon atoms”. Same as “Example”.
  • aromatic heterocyclic group in the “optionally substituted aromatic heterocyclic group” include phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, Indolyl group, furazanyl group, oxazolyl group, oxazolopyrazinyl group, oxazolopyridinyl group, oxazolopyridazinyl group, oxazolopyrimidinyl group, quinazolinyl group, quinoxalinyl group, quinolyl group, cinnolinyl group, thiadiazolyl group , Thiazolyl group, thiazolopyrazinyl group, thiazolopyridyl group, thiazolopyridazinyl group, thiazolopyrimidinyl group, thienyl group, triazinyl group, triazolyl group,
  • (I) at least one hydrogen atom as Fy is substituted with an optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring;
  • Preferred examples of the “alkyl group having 1 to 18 carbon atoms which may have a substituent other than the cyclic group” include structures represented by the following formulas (3-1) to (3-11): Is mentioned.
  • the present invention is not limited to the following.
  • “*” represents a position bonded to Yy
  • “ ⁇ ” extending from the inside of the ring represents a bond extending from an arbitrary position on the ring.
  • the groups represented by the following formulas (3-1) to (3-11) may have a substituent.
  • Specific examples of the substituent include the above-mentioned ““ having a substituent. The same as the “specific examples of substituents” in the “cyclic group having 2 to 30 carbon atoms”.
  • the “alkyl group having 1 to 18 carbon atoms” in the “optionally substituted alkyl group having 1 to 18 carbon atoms” may have one or more substituents.
  • the “plural substituents” may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Examples of “(ii) a cyclic group having 2 to 30 carbon atoms which has at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring and may have a substituent” as Fy include, for example, (ii-1 ) An optionally substituted hydrocarbon ring group having 6 to 30 carbon atoms, having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms; and (ii-2) an aromatic having 6 to 18 carbon atoms.
  • a heterocyclic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring having 2 to 30 carbon atoms, an optionally substituted heterocyclic group having 2 to 30 carbon atoms, and the like Preferably mentioned.
  • hydrocarbon ring group in the above “(ii-1) optionally having a hydrocarbon ring group having 6 to 30 carbon atoms, which has an aromatic hydrocarbon ring having 6 to 30 carbon atoms”.
  • phenyl group (6 carbon atoms), naphthyl group (10 carbon atoms), anthracenyl group (14 carbon atoms), phenanthrenyl group (14 carbon atoms), pyrenyl group (16 carbon atoms), fluorenyl
  • An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as a group (carbon number 13); an indanyl group (9 carbon atoms); a 1,2,3,4-tetrahydronaphthyl group (10 carbon atoms); Dihydronaphthyl group (10 carbon atoms); and the like.
  • Specific examples of the “(ii-1) at least one hydrocarbon ring group having 6 to 30 carbon atoms, which may have a substituent and having 6 to 30 carbon atoms” include: Examples thereof include groups having structures represented by the following formulas (1-1) to (1-21). The groups having the structures represented by the following formulas (1-1) to (1-21) may have a substituent. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”. In the following formulas (1-1) to (1-21), “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
  • aromatic hydrocarbon ring having 6 to 18 carbon atoms having a substituent having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • aromatic hydrocarbon ring having 6 to 18 carbon atoms having an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • heterocyclic group in the “heterocyclic group having 2 to 30 carbon atoms” include, for example, phthalimide group, 1-benzofuranyl group, 2-benzofuranyl group, acridinyl group, isoquinolinyl group, imidazolyl group, indolyl group, and flazanyl group.
  • “-” extending from the inside of the ring represents a bond with Yy extending from any position of the ring.
  • X represents —CH 2 —, —NR c —, an oxygen atom, a sulfur atom, —SO— or —SO 2 —
  • Y and Z each independently represent —NR c —, an oxygen atom, a sulfur atom, —SO— or —SO 2 —
  • E represents —NR c —, an oxygen atom or a sulfur atom.
  • R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group. (However, in each formula, oxygen atom, sulfur atom, —SO—, and —SO 2 — are not adjacent to each other.)]
  • the “(ii) optionally substituted cyclic group having 2 to 30 carbon atoms and having at least one of an aromatic hydrocarbon ring and an aromatic heterocyclic ring” has one or more substituents. May be. When it has a plurality of substituents, the plurality of substituents may be the same as or different from each other. Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Fy is preferably a group having a structure represented by any of the following formulas (i-1) to (i-9), and the following formula (ii-1) A group having a structure represented by any one of (ii-20) is particularly preferred.
  • Ar is a group having a structure represented by (II-2) or (II-3)
  • Fy is a group having a structure represented by any of the following (i-1) to (i-13): It is preferably a group having a structure represented by any of the following formulas (ii-1) to (ii-26).
  • the group having a structure represented by any of the following formulas (i-1) to (i-13) and the following formulas (ii-1) to (ii-26) may have a substituent.
  • Specific examples of the substituent are the same as the above-described “specific examples of the substituent in the cyclic group having 2 to 30 carbon atoms which may have a substituent”.
  • Y represents the same meaning as described above.
  • “*” represents the position where Yy is bonded, and “ ⁇ ” extends from the inside of the ring. Represents a bond extending from any position of the ring.
  • the total number of ⁇ electrons contained in the ring structure in Fy is preferably 8 or more, more preferably 10 or more, and 20 or less. Preferably, it is 18 or less.
  • Ar is a group having a structure represented by (II-2) or (II-3)
  • the total number of ⁇ electrons contained in the ring structure in Fy is preferably 4 or more, and is 6 or more. More preferably, it is preferably 20 or less, and more preferably 18 or less.
  • -Ax- Ax represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Ax is preferably any one of the following (1) to (5).
  • hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms examples include groups represented by the following structural formula.
  • the group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
  • substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax include a fluorine atom, a chlorine atom, etc.
  • a cyano group an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group or a propyl group; an alkenyl group having 2 to 6 carbon atoms such as a vinyl group or an allyl group; one such as a trifluoromethyl group
  • An alkoxy group having 1 to 6 carbon atoms such as a propoxy group; a
  • R b and R a are each the same meanings as defined above, the preferred examples are also the same as above.
  • at least one substituent selected from the group consisting of a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms is preferable.
  • “Aromatic hydrocarbon ring having 6 to 30 carbon atoms” in “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax Specific examples include a benzene ring, a naphthalene ring, a fluorene ring, and the like.
  • ring group having at least one aromatic ring selected from the group consisting of (2) an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms as -Ax Heterocyclic group ”
  • Specific examples of the “ring group” include, for example, groups represented by the following structural formulas. The group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later.
  • R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group, and “ ⁇ ” extending from the inside of the ring represents any position of the ring. Represents a bond that extends from ]
  • Specific examples of the substituent of the “cyclic group” include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms”. is there.
  • aromatic hydrocarbon ring having 6 to 30 carbon atoms include, for example, benzene ring, naphthalene ring, fluorene ring, anthracene ring and the like.
  • aromatic heterocycle having 2 to 30 carbon atoms in “ring group” include, for example, thiophene ring, furan ring, pyridine ring, pyrazine ring, pyrimidine ring, triazine ring, pyrrole ring, imidazole ring, thiazole ring.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • Specific examples of the “alkyl group having 1 to 12 carbon atoms” include, for example, methyl group, ethyl group, propyl group, isopropyl group, and the like.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
  • an alkyl group having 1 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax -
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • Specific examples of the “alkenyl group having 2 to 12 carbon atoms” include, for example, a vinyl group and an allyl group.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents include specific examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax; The preferred examples thereof are the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. The same.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in the above Ay.
  • an alkenyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms include the same examples as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax - “(5) an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms” as Ax
  • Specific examples include ethynyl group, propynyl group, and the like.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • substituents are the same as those of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax.
  • the preferred examples thereof are also the same as the preferred examples of the substituent of “(1) a hydrocarbon ring group having 6 to 40 carbon atoms having at least one aromatic hydrocarbon ring having 6 to 30 carbon atoms” as Ax. .
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic hydrocarbon ring group having 6 to 30 carbon atoms are the same as the specific examples of the “aromatic hydrocarbon ring group having 6 to 30 carbon atoms” in Ay.
  • an alkynyl group having 2 to 12 carbon atoms substituted with at least one of an aromatic hydrocarbon ring group having 6 to 30 carbon atoms and an aromatic heterocyclic group having 2 to 30 carbon atoms as Ax
  • aromatic heterocyclic group having 2 to 30 carbon atoms are the same as the specific examples of the “aromatic heterocyclic group having 2 to 30 carbon atoms” in Ay.
  • Ax is preferably any one of groups represented by the following structural formula.
  • the group represented by the following structural formula may have a substituent. Specific examples of the substituent are the same as the “specific examples of substituent that Ax has” described later. [In each formula, “-” extending from the inside of the ring represents a bond extending from any position of the ring. ]
  • Ax is more preferably any one of the groups represented by the following structural formula.
  • Ax is particularly preferably any one of groups represented by the following structural formula.
  • Ax may have a substituent.
  • substituents of Ax include, for example, halogen atoms such as fluorine atom and chlorine atom; cyano group; alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group and propyl group; vinyl group, An alkenyl group having 2 to 6 carbon atoms such as an allyl group; an alkyl group having 1 to 6 carbon atoms in which one or more hydrogen atoms such as a trifluoromethyl group are substituted with a halogen atom such as a fluorine atom; An N, N-dialkylamino group having 2 to 12 carbon atoms; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and an isopropoxy group; a nitro group; —OCF 3 ; —C ( ⁇ O) —R b —O—C ( ⁇ O) —R b
  • -Az- Az represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aromatic heterocyclic ring having 2 to 30 carbon atoms.
  • Az excludes the case of C (Ay) Ax.
  • Az is preferably any of the following (1) and (2).
  • Az is more preferably any one of the groups represented by the following structural formula.
  • R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group.
  • Ar is preferably represented by any of the following formulas (III-1) to (III-6), more preferably the following formula (III-1), the following formula (III-2), the following formula (III) -4) or the following formula (III-5), particularly preferably the following formula (III-1) or the following formula (III-4).
  • the substituent may have an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group.
  • Ax, Ay, Az and Q have the same meaning as described above, and preferred examples thereof are also the same as above, and * represents Z 1 or Z 2. Represents that it is combined with.
  • * represents a position bonded to Ar
  • R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Z 1 and Z 2 are each independently a chemical single bond, —O—, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —, * —CH 2.
  • a 1 and A 2 each independently represents a divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent.
  • the chain aliphatic group includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, — NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — may be present.
  • —O— or —S— are adjacent to each other is excluded.
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Provided that the carbon atom bonded to Z 1 and the carbon atom bonded to Y 1 or Y 3 of A 1 and the carbon atom bonded to Z 2 and the carbon atom bonded to Y 2 or Y 4 of A 2 are bonded to each other. , —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, —NR 12 —C ( ⁇ O) There is no substitution with —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) —.
  • divalent chain aliphatic group having 1 to 20 carbon atoms in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, , Methylene group, ethylene group, hexamethylene group, propylene group, tetramethylene group, pentamethylene group, hexamethylene group, octamethylene group, decamethylene group [— (CH 2 ) 10 —], etc.
  • Alkylene group vinylene group, 1-methylvinylene group, propenylene group, 1-butenylene group, 2-butenylene group, 1-pentenylene group, 2-pentenylene group, etc., alkenylene group having 2 to 20 carbon atoms; 1,3-pentadienyl group And groups having a conjugated diene having 2 to 20 carbon atoms such as a 1,3-hexadienyl group.
  • a divalent saturated chain aliphatic group having 2 to 20 carbon atoms and a divalent unsaturated chain aliphatic group having 2 to 20 carbon atoms are preferable, and a divalent saturated chain having 3 to 20 carbon atoms.
  • aliphatic aliphatic groups divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms
  • divalent unsaturated chain aliphatic groups having 2 to 20 carbon atoms vinylene group, propylene group and propylene group.
  • a nylene group and a butenylene group are preferred.
  • the “C 1-20 divalent chain aliphatic group” includes —O—, —S—, —O—C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —O—, —NR 12 —C ( ⁇ O) —, —C ( ⁇ O) —NR 12 —, —NR 12 —, or —C ( ⁇ O) — interposed (However, the case where two or more of —O— or —S— are adjacent to each other is excluded).
  • R 12 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and is preferably a hydrogen atom or a methyl group.
  • substituent in the “divalent chain aliphatic group having 1 to 20 carbon atoms which may have a substituent” include, for example, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Halogen atom carbon number such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. 1-6 alkoxy groups; and the like.
  • a fluorine atom, a methoxy group, and an ethoxy group are preferable.
  • B 1 and B 2 each independently represent a cyclic aliphatic group that may have a substituent or an aromatic group that may have a substituent, and have a substituent.
  • a cyclic aliphatic group having 5 to 20 carbon atoms or an aromatic group having 2 to 20 carbon atoms which may have a substituent is preferable.
  • cycloaliphatic group in the “optionally substituted cycloaliphatic group” include cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cycloheptane, and the like.
  • cycloalkanediyl groups such as 1,4-diyl, cyclooctane-1,5-diyl; carbons such as decahydronaphthalene-1,5-diyl and decahydronaphthalene-2,6-diyl And a bicycloalkanediyl group of 5 to 20;
  • the cycloaliphatic group is preferably a cycloalkanediyl group having 5 to 20 carbon atoms, more preferably a cyclohexanediyl group, and particularly preferably a cyclohexane-1,4-diyl group.
  • the “cycloaliphatic group” may be a trans isomer, a cis isomer, or a mixture of a cis isomer and a trans isomer, but a trans isomer is more preferable.
  • aromatic group in the “aromatic group optionally having substituent (s)” include, for example, 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, An aromatic hydrocarbon ring group having 6 to 18 carbon atoms such as 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 4,4′-biphenylene group; furan-2,5- And aromatic heterocyclic groups having 2 to 20 carbon atoms such as diyl, thiophene-2,5-diyl, pyridine-2,5-diyl and pyrazine-2,5-diyl.
  • an aromatic hydrocarbon ring group having 6 to 18 carbon atoms is preferable, a phenylene group is more preferable, and a 1,4-phenylene group is particularly preferable.
  • substituents in the “optionally substituted cycloaliphatic group” and the “optionally substituted aromatic group” include, for example, a halogen atom, an alkyl having 1 to 6 carbon atoms. Group, an alkoxy group having 1 to 5 carbon atoms, a nitro group, a cyano group, and the like.
  • the cycloaliphatic group and the aromatic group may have at least one substituent selected from the above-described substituents.
  • each substituent may be the same or different.
  • R 13 and R 14 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Y 1 to Y 4 are preferably each independently a single bond, —O—, —C ( ⁇ O) —O—, or —O—C ( ⁇ O) —, More preferably, they are O—, —C ( ⁇ O) —O—, or —O—C ( ⁇ O) —.
  • G 1 and G 2 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and 1 of a methylene group (—CH 2 —) contained in an aliphatic hydrocarbon group having 3 to 20 carbon atoms.
  • the above is an organic group of any of the groups substituted with —O— or —C ( ⁇ O) —.
  • a hydrogen atom contained in the organic group of G 1 and G 2 may be substituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom.
  • the methylene groups (—CH 2 —) at both ends of G 1 and G 2 are not substituted with —O— or —C ( ⁇ O) —.
  • aliphatic hydrocarbon group having 1 to 20 carbon atoms and the “aliphatic hydrocarbon group having 3 to 20 carbon atoms” include an alkylene group having 1 to 20 carbon atoms and a carbon number, respectively. Examples include 3 to 20 alkylene groups. Among these, n-butylene group, n-hexylene group, n-octylene group, and n-decamethylene group [— (CH 2 ) 10 —] are preferable.
  • P 1 and P 2 each independently represent a polymerizable group.
  • the polymerizable group include a group represented by CH 2 ⁇ CR 31 —C ( ⁇ O) —O— such as acryloyloxy group and methacryloyloxy group (R 31 is a hydrogen atom, methyl group) Or a chlorine atom.), Vinyl group, vinyl ether group, p-stilbene group, acryloyl group, methacryloyl group, carboxyl group, methylcarbonyl group, hydroxyl group, amide group, alkylamino group having 1 to 4 carbon atoms, amino group , Epoxy group, oxetanyl group, aldehyde group, isocyanate group or thioisocyanate group.
  • a group represented by CH 2 ⁇ CR 31 —C ( ⁇ O) —O— is preferable, and a group represented by CH 2 ⁇ CH—C ( ⁇ O) —O— (acryloyloxy group), A group represented by CH 2 ⁇ C (CH 3 ) —C ( ⁇ O) —O— (methacryloyloxy group) is more preferred, and an acryloyloxy group is particularly preferred.
  • ⁇ P, q> p and q each independently represents an integer of 0 to 2.
  • p and q are each independently 1.
  • B 1 and B 2 in the aforementioned formula (I) are preferably each independently an aromatic group which may have a substituent.
  • An aromatic group having 6 to 18 carbon atoms which may have a group is more preferable, and a phenylene group is particularly preferable.
  • the polymerizable compound (I) is not particularly limited, but has a symmetric structure centered on Ar (that is, Z 1 and Z 2 , A 1 and A 2 , Y 1 and Y 2 , B 1 and B 2 , n and m, Y 3 and Y 4 , G 1 and G 2 , and P 1 and P 2 are preferably the same (symmetric about Ar).
  • the above-described polymerizable liquid crystal compound (I) can be synthesized by combining known synthetic reactions. That is, various documents (for example, International Publication No. 2012/141245, International Publication No. 2012/147904, International Publication No. 2014/010325, International Publication No. 2013/046871, International Publication No. 2014/061709, International Publication No. 2014/126113, International Publication No. 2015/064698, International Publication No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016/159193, International Publication No. 2012 / 169424, International Publication No. 2012/176679, International Publication No. 2015/122385 and the like.
  • the polymerizable liquid crystal composition contains at least a polymerizable liquid crystal compound (I) and a polymerization initiator.
  • the polymerizable liquid crystal composition is useful as a raw material for producing the polymer, optical film, and optical anisotropic body of the present invention, as will be described later. According to the polymerizable liquid crystal composition of the present invention, it is possible to satisfactorily produce an optical film or the like having ideal wavelength dispersion exhibiting broadband properties, that is, reverse wavelength dispersion.
  • a polymerization initiator is mix
  • a radical polymerization initiator, an anionic polymerization initiator, a cationic polymerization initiator, etc. are mentioned.
  • radical polymerization initiator a thermal radical generator which is a compound that generates an active species capable of initiating polymerization of a polymerizable liquid crystal compound by heating; visible light, ultraviolet light (i-line etc.), far ultraviolet light, Any of radical photogenerators, which are compounds that generate active species capable of initiating polymerization of a polymerizable liquid crystal compound upon exposure to exposure light such as an electron beam or X-ray, can be used. It is preferred to use.
  • Photoradical generators include acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, ⁇ -diketone compounds, polynuclear quinone compounds , Xanthone compounds, diazo compounds, imide sulfonate compounds, and the like. These compounds are components that generate active radicals or active acids or both active radicals and active acids upon exposure.
  • a photoradical generator can be used individually by 1 type or in combination of 2 or more types.
  • acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, And 1- [4- (phenylthio) phenyl] -octane-1,2-dione 2- (O-benzoyloxime).
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2 , 2'-bis (2-bromophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'-tetraphenyl-1 , 2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimi
  • the hydrogen donor means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
  • the hydrogen donor mercaptan compounds, amine compounds and the like defined below are preferable.
  • mercaptan compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-2,5-dimethyl.
  • An aminopyridine etc. can be mentioned.
  • amine compounds include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, ethyl-4-dimethylaminobenzoate, Examples include 4-dimethylaminobenzoic acid and 4-dimethylaminobenzonitrile.
  • triazine compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- (5 -Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl)- s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) ethenyl -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl)
  • O-acyloxime compounds include 1- [4- (phenylthio) phenyl] -heptane-1,2-dione 2- (O-benzoyloxime), 1- [4- (phenylthio) phenyl]- Octane-1,2-dione 2- (O-benzoyloxime), 1- [4- (benzoyl) phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [9-ethyl- 6- (2-Methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), 1- [9-ethyl-6- (3-methylbenzoyl) -9H-carbazole-3- Yl] -ethanone 1- (O-acetyloxime), 1- (9-ethyl-6-benzoyl-9H-carbazol-3-yl) -ethanone 1- (O-acetyloxime), 1-
  • anionic polymerization initiator examples include alkyl lithium compounds; monolithium salts or monosodium salts such as biphenyl, naphthalene, and pyrene; polyfunctional initiators such as dilithium salts and trilithium salts;
  • Examples of the cationic polymerization initiator include proton acids such as sulfuric acid, phosphoric acid, perchloric acid and trifluoromethanesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, titanium tetrachloride and tin tetrachloride; A combined system of a group onium salt or an aromatic onium salt and a reducing agent.
  • polymerization initiators can be used singly or in combination of two or more.
  • the blending ratio of the polymerization initiator is usually 0.1 to 30 parts by mass, preferably 0.1 to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. 5 to 10 parts by mass.
  • the polymerizable liquid crystal composition preferably contains a surfactant in order to adjust the surface tension.
  • the surfactant is not particularly limited, but a nonionic surfactant is usually preferable.
  • commercially available products may be used.
  • nonionic surfactants that are oligomers containing fluorine-containing groups, hydrophilic groups, and lipophilic groups, such as Surflon manufactured by AGC Seimi Chemical Co., Ltd.
  • these surfactants may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
  • the blending ratio of the surfactant is usually 0.01 to 10 parts by mass, preferably 0 with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. .01 to 2 parts by mass.
  • the polymerizable liquid crystal composition may further contain other components in addition to the polymerizable liquid crystal compound, the polymerization initiator, and the surfactant as long as the effects of the present invention are not affected.
  • Other components include metals, metal complexes, dyes, pigments, fluorescent materials, phosphorescent materials, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants, ion exchange resins, Examples thereof include metal oxides such as titanium oxide.
  • other components include other copolymerizable monomers. Specifically, it is not particularly limited.
  • the polymerizable liquid crystal composition is usually prepared by mixing and dissolving a predetermined amount of a polymerizable liquid crystal compound, a polymerization initiator, and other components blended as required in an appropriate organic solvent. Can do.
  • Organic solvents to be used include ketones such as cyclopentanone, cyclohexanone and methyl ethyl ketone; acetate esters such as butyl acetate and amyl acetate; halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane; 1,4-dioxane, cyclopentylmethyl And ethers such as ether, tetrahydrofuran, tetrahydropyran, and 1,3-dioxolane;
  • ketones such as cyclopentanone, cyclohexanone and methyl ethyl ketone
  • acetate esters such as butyl acetate and amyl acetate
  • halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane
  • 1,4-dioxane 1,4-dioxane
  • cyclopentylmethyl And ethers such as
  • polymer of the present invention is obtained by polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition.
  • “polymerization” means a chemical reaction in a broad sense including a crosslinking reaction in addition to a normal polymerization reaction.
  • the polymer of the present invention usually has a monomer unit derived from the polymerizable liquid crystal compound (I) (for example, the repeating unit (I) ′).
  • Y 1 to Y 4 , A 1 , A 2 , B 1 , B 2 , G 1 , G 2 , p, and q in the formula (I) ′ have the same meaning as described above, and preferred examples thereof Is the same.
  • R 31 is a hydrogen atom, a methyl group, or a chlorine atom, and among them, a hydrogen atom or a methyl group is preferable.
  • the polymer of the present invention is prepared using the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition, it can be favorably used as a constituent material for optical films and the like. .
  • the polymer of the present invention is not particularly limited, and can be used in any shape according to the application such as a film shape, a powder shape, or a layer shape in which powders are aggregated.
  • the polymer film can be used favorably as a constituent material of the optical film and optical anisotropic body described later, and the polymer powder can be used for paints, anti-counterfeit articles, security articles, etc.
  • the layer made of polymer powder can be used favorably as a constituent material of the optical anisotropic body.
  • the polymer of the present invention ( ⁇ ) was subjected to a polymerization reaction of the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition in the presence of a suitable organic solvent. Then, the target polymer is isolated, and the resulting polymer is dissolved in an appropriate organic solvent to prepare a solution. After coating the solution on an appropriate substrate and drying the resulting coating, ( ⁇ ) The above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition is dissolved in an organic solvent, and this solution is applied onto a substrate by a known coating method. After coating, it can be suitably produced by a method of performing a polymerization reaction by removing the solvent and then heating or irradiating active energy rays.
  • the polymerizable liquid crystal compound (I) described above may be polymerized alone.
  • the organic solvent used for the polymerization reaction in the method ( ⁇ ) is not particularly limited as long as it is inactive.
  • aromatic hydrocarbons such as toluene, xylene and mesitylene
  • ketones such as cyclohexanone, cyclopentanone and methyl ethyl ketone
  • acetate esters such as butyl acetate and amyl acetate
  • halogenated hydrocarbons such as chloroform, dichloromethane and dichloroethane
  • ethers such as cyclopentyl methyl ether, tetrahydrofuran and tetrahydropyran;
  • those having a boiling point of 60 to 250 ° C. are preferable and those having a temperature of 60 to 150 ° C. are more preferable from the viewpoint of excellent handleability.
  • an organic solvent for dissolving the isolated polymer and an organic solvent used in the method ( ⁇ ) include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, Ketone solvents such as cyclohexanone; ester solvents such as butyl acetate and amyl acetate; halogenated hydrocarbon solvents such as dichloromethane, chloroform and dichloroethane; tetrahydrofuran, tetrahydropyran, 1,2-dimethoxyethane, 1,4-dioxane, Ether solvents such as cyclopentyl methyl ether and 1,3-dioxolane; N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, N-methylpyrrolidone (N-methyl-2-pyrrolidone), etc.
  • Non-proton Polar solvent such as
  • a known and commonly used material can be used regardless of organic or inorganic.
  • the organic material include polycycloolefins (for example, ZEONEX, ZEONOR (registered trademark; manufactured by ZEON CORPORATION), ARTON (registered trademark; manufactured by JSR), and APPEL (registered trademark; manufactured by Mitsui Chemicals)),
  • examples of the organic material include polycycloolefins (for example, ZEONEX, ZEONOR (registered trademark; manufactured by ZEON CORPORATION), ARTON (registered trademark; manufactured by JSR), and APPEL (registered trademark; manufactured by Mitsui Chemicals))
  • examples include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, cellulose, cellulose triacetate, polyethersulfone, etc.
  • inorganic materials include silicon, glass, cal
  • the substrate used may be a single layer or a laminate.
  • a substrate made of an organic material is preferable, and a resin film obtained by forming an organic material into a film is more preferable.
  • substrate the board
  • a known method can be used as a method of applying a polymer solution to a substrate in the method ( ⁇ ) and a method of applying a solution for polymerization reaction to a substrate in the method ( ⁇ ).
  • curtain coating method, extrusion coating method, roll coating method, spin coating method, dip coating method, bar coating method, spray coating method, slide coating method, print coating method, gravure coating method, die coating method A cap coating method or the like can be used.
  • the drying temperature is not particularly limited as long as the solvent can be removed from the solvent, but the lower limit temperature is preferably 50 ° C. or higher from the viewpoint that a constant temperature can be stably obtained, and is 70 ° C. or higher. More preferably.
  • the upper limit temperature of the drying temperature is preferably 200 ° C. or less, more preferably 195 ° C. or less, from the viewpoint of a range that does not adversely affect the substrate.
  • Examples of a method for polymerizing the above-described polymerizable liquid crystal compound (I) or the above-described polymerizable liquid crystal composition include a method of irradiating active energy rays, a thermal polymerization method, and the like.
  • the method of irradiating with active energy rays is preferable because the reaction proceeds at.
  • a method of irradiating light such as ultraviolet rays is preferable because the operation is simple.
  • the temperature at which the light such as ultraviolet rays is irradiated is not particularly limited as long as the liquid crystal phase can be maintained. However, the lower limit temperature is 15 ° C. or more from the viewpoint that the photopolymerization can proceed stably.
  • the temperature is 20 ° C. or higher.
  • the upper limit temperature for irradiating light such as ultraviolet rays is preferably 200 ° C. or lower, and more preferably 195 ° C. or lower, from the viewpoint of not adversely affecting the substrate.
  • the temperature at the time of light irradiation is preferably 100 ° C. or less.
  • the light irradiation intensity is usually in the range of 1 W / m 2 to 10 kW / m 2 , preferably in the range of 5 W / m 2 to 2 kW / m 2 .
  • the dose of ultraviolet rays is preferably 0.1 mJ / cm 2 or more, more preferably 0.5 mJ / cm 2 or more, preferably 5000 mJ / cm 2 or less, more preferably 4000 mJ / cm 2 or less.
  • the polymer obtained as described above can be used by being transferred from the substrate, separated from the substrate and used alone, or as a constituent material of an optical film or the like without being separated from the substrate. You can also The polymer peeled from the substrate can be used after being pulverized by a known method to form a powder.
  • the number average molecular weight of the polymer of the present invention obtained as described above is preferably 500 to 500,000, more preferably 5,000 to 300,000. If the number average molecular weight is in such a range, it is desirable because high hardness can be obtained and handleability is excellent.
  • the number average molecular weight of the polymer can be measured by gel permeation chromatography (GPC) using monodispersed polystyrene as a standard sample and tetrahydrofuran as an eluent.
  • the optical film of the present invention is formed using the polymer and / or polymerizable liquid crystal compound of the present invention, and includes a layer having an optical function.
  • the optical function means simple transmission, reflection, refraction, birefringence and the like.
  • the optical film of the present invention is an optical film comprising the polymer of the present invention as a main constituent material of the layer having an optical function, or the layer having an optical function is the polymerizable liquid crystal of the present invention. It can be an optical film containing a compound.
  • the occupation ratio of the polymer of the present invention is more than 50% by mass when all the components of the layer having an optical function are 100% by mass. is there.
  • the polymerizable liquid crystal compound of the present invention is added in an amount of 0.01% by mass when the total components of the layer having an optical function are 100% by mass. % Or more.
  • the optical film of the present invention is in the form (alignment substrate / (alignment film) / optical film) formed on the alignment substrate which may have an alignment film, and a transparent substrate film different from the alignment substrate.
  • the optical film may be transferred in any form (transparent substrate film / optical film), or in the case where the optical film is self-supporting, it may be in any form of an optical film single layer (optical film).
  • the alignment film and the alignment substrate the same substrate and alignment film as the optical anisotropic body described later can be used as the alignment film and the alignment substrate.
  • the optical film of the present invention is obtained by applying (A) a solution containing the polymerizable liquid crystal compound of the present invention or a solution of the polymerizable liquid crystal composition onto an alignment substrate, drying the obtained coating film, and subjecting to heat treatment. (Liquid crystal orientation), a method of performing light irradiation and / or heat treatment (polymerization), and (B) a liquid crystalline polymer obtained by polymerizing the polymerizable liquid crystal compound or polymerizable liquid crystal composition of the present invention. Or a solution containing the polymerizable liquid crystal compound of the present invention and a resin is applied on the alignment substrate, and the resulting coating is obtained. It can be produced by a method of drying the membrane.
  • the optical film of the present invention can be used for optical anisotropic bodies, alignment films for liquid crystal display elements, color filters, low-pass filters, light polarizing prisms, various optical filters, and the like.
  • the optical film of the present invention can be obtained from the phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan.
  • the following ⁇ value and ⁇ value are preferably within a predetermined range. Specifically, the ⁇ value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90. Further, the ⁇ value is preferably 1.00 to 1.25, and more preferably 1.01 to 1.20.
  • ⁇ (phase difference at 450 nm) / (phase difference at 550 nm)
  • ⁇ (phase difference at 650 nm) / (phase difference at 550 nm)
  • the optical anisotropic body of this invention has a layer which uses the polymer of this invention as a constituent material.
  • the optical anisotropic body of the present invention can be obtained, for example, by forming an alignment film on a substrate and further forming a layer (liquid crystal layer) made of the polymer of the present invention on the alignment film.
  • the optically anisotropic body of the present invention may be one in which a layer made of the polymer of the present invention (liquid crystal layer) is directly formed on a substrate, or a layer made of the polymer of the present invention (liquid crystal layer). It may consist of only.
  • the polymer layer may be a film polymer or a powder polymer aggregate.
  • the alignment film is formed on the surface of the substrate in order to regulate the alignment of the polymerizable liquid crystal compound in one direction in the plane.
  • the alignment film is formed by applying a solution containing a polymer such as polyimide, polyvinyl alcohol, polyester, polyarylate, polyamideimide, or polyetherimide (alignment film composition) onto a substrate, drying the film, and then unidirectionally. It can be obtained by rubbing treatment.
  • the thickness of the alignment film is preferably 0.001 to 5 ⁇ m, and more preferably 0.001 to 1.0 ⁇ m.
  • the rubbing treatment method is not particularly limited, and examples thereof include a method of rubbing the alignment film in a certain direction with a roll made of a synthetic fiber such as nylon or a natural fiber such as cotton or a felt.
  • a method of regulating the alignment in one direction in the plane can be provided by a method of irradiating the surface of the alignment film with polarized ultraviolet rays.
  • Examples of the substrate on which the alignment film is formed include a glass substrate and a substrate made of a synthetic resin film.
  • the synthetic resin include acrylic resin, polycarbonate resin, polyethersulfone resin, polyethylene terephthalate resin, polyimide resin, polymethyl methacrylate resin, polysulfone resin, polyarylate resin, polyethylene resin, polystyrene resin, polyvinyl chloride resin, and cellulose diacetate. , Cellulose triacetate, and thermoplastic resins such as alicyclic olefin polymers.
  • Examples of the alicyclic olefin polymer include cyclic olefin random multicomponent copolymers described in JP-A No. 05-310845, US Pat. No. 5,179,171, JP-A No. 05-97978, and US Pat. No. 5,202,388. And hydrogenated polymers described in Japanese Patent Application Laid-Open No. 11-124429 (International Publication No. 99/20676), and thermoplastic dicyclopentadiene ring-opening polymers and hydrogenated products thereof. .
  • the same method as described in the section of the polymer of the present invention (the above ( ⁇ ) and ( ⁇ )) may be used. Can be mentioned.
  • the thickness of the obtained liquid crystal layer is not particularly limited, but is usually 1 to 10 ⁇ m.
  • phase difference plate a viewing angle expansion plate, etc.
  • viewing angle expansion plate etc.
  • the optical anisotropic body of the present invention is obtained from a phase difference at a wavelength of 400 nm to 800 nm measured with Mueller Matrix Polarimeter Axoscan.
  • the following ⁇ value and ⁇ value are preferably within a predetermined range. Specifically, the ⁇ value is preferably 0.70 to 0.99, and more preferably 0.75 to 0.90.
  • the ⁇ value is preferably 1.00 to 1.25, more preferably 1.01 to 1.25.
  • ⁇ (phase difference at 450 nm) / (phase difference at 550 nm)
  • ⁇ (phase difference at 650 nm) / (phase difference at 550 nm)
  • the polarizing plate of the present invention comprises the optical anisotropic body of the present invention and a polarizing film.
  • Specific examples of the polarizing plate of the present invention include those in which the optical anisotropic body of the present invention is laminated on a polarizing film directly or via another layer (glass plate or the like).
  • the manufacturing method of the polarizing film is not particularly limited.
  • a method for producing a PVA-based polarizing film a method of stretching uniaxially after iodine ions are adsorbed on a PVA-based film, a method of adsorbing iodine ions after stretching a uniaxially stretched PVA-based film, A method of simultaneously performing iodine ion adsorption and uniaxial stretching, a method of stretching a uniaxial film after dyeing a PVA film with a dichroic dye, a method of dyeing a dichroic dye after stretching a PVA film uniaxially, a PVA system
  • staining with a dichroic dye and uniaxial stretching to a film is mentioned.
  • a method for producing a polyene polarizing film a method of heating and dehydrating in the presence of a dehydration catalyst after stretching a PVA film uniaxially, a method of stretching a polyvinyl chloride film uniaxially and then in the presence of a dehydrochlorination catalyst And a known method such as heating and dehydrating.
  • the polarizing film and the optical anisotropic body of the present invention may be in contact with each other via an adhesive layer made of an adhesive (including an adhesive).
  • the average thickness of the adhesive layer is usually 0.01 ⁇ m to 30 ⁇ m, preferably 0.1 ⁇ m to 15 ⁇ m.
  • the adhesive layer is preferably a layer having a tensile fracture strength according to JIS K7113 of 40 MPa or less.
  • Adhesives constituting the adhesive layer include acrylic adhesives, urethane adhesives, polyester adhesives, polyvinyl alcohol adhesives, polyolefin adhesives, modified polyolefin adhesives, polyvinyl alkyl ether adhesives, rubber adhesives, vinyl chloride Vinyl acetate adhesive, styrene / butadiene / styrene copolymer (SBS copolymer) adhesive, hydrogenated product (SEBS copolymer) adhesive, ethylene / vinyl acetate copolymer, ethylene-styrene copolymer, etc.
  • SBS copolymer vinyl chloride Vinyl acetate adhesive
  • SEBS copolymer hydrogenated product
  • Ethylene adhesives and acrylic ester adhesives such as ethylene / methyl methacrylate copolymers, ethylene / methyl acrylate copolymers, ethylene / ethyl methacrylate copolymers and ethylene / ethyl acrylate copolymers, etc. Is mentioned.
  • the polarizing plate of the present invention uses the optical anisotropic body of the present invention, it has excellent in-plane uniformity of optical characteristics while having reverse wavelength dispersion.
  • a display device provided with a panel and an antireflection film can be suitably produced.
  • the panel include a liquid crystal panel and an organic electroluminescence panel.
  • the display device include a flat panel display device including a polarizing plate and a liquid crystal panel, and an organic electroluminescence display device including a liquid crystal panel and an organic electroluminescence panel.
  • the polymerizable liquid crystal compound of the present invention and the intermediate that can be used for the preparation of the polymerizable liquid crystal compound are WO 2012/141245, WO 2012/147904, WO 2014/010325, and WO 2013/046781, International Publication No. 2014/126113, International Publication No. 2015/025793, Japanese Patent Application Laid-Open No. 2015-140302, International Publication No. 2015/129654, International Publication No. 2015/141784, International Publication No. 2016 / It can be synthesized with reference to No. 159193.
  • the structure of an intermediate that can be used for the preparation of the polymerizable liquid crystal compound of the present invention is represented, for example, by the following general formula (X-1).
  • P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p each represents the same meaning as described above, and preferred examples thereof also represent the P 1 , G 1 , Y 3 , B 1 , Y 1 , A 1 , p are the same as the preferred examples, and FG represents a hydroxyl group or a carboxyl group.
  • Y are as defined above Y 1, Y 2, the preferred embodiment is also the same as the preferred examples of the Y 1, Y 2, a are as defined above a 1, a 2, The preferred examples are the same as the preferred examples of A 1 and A 2 . ]
  • a compound represented by the general formula (X1) (hereinafter referred to as “compound (X1)”) and a compound represented by the general formula (X2) (hereinafter referred to as “compound (X2)”) are present in a base.
  • compound (X1) a compound represented by the general formula (X2)
  • compound (X2) a compound represented by the general formula (X2)
  • compound (X) By reacting under the above conditions, a compound represented by the general formula (X) (hereinafter referred to as “compound (X)”) can be obtained.
  • the amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). More preferably, it is usually 1.5 molar equivalents or less, and more preferably 1.3 molar equivalents or less.
  • Examples of the base used include tertiary amines such as triethylamine, pyridine, diisopropylethylamine, and N, N-dimethyl-4-aminopyridine;
  • the amount of the base used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of compound (X2). Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • the compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a dicarboxylic acid using a dehydrating condensing agent.
  • the amount of compound (X1) used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • the condensing agent to be used examples include dehydrating condensing agents such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride;
  • the amount of the condensing agent to be used is usually 0.1 molar equivalents or more, preferably 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, based on the usage amount of the dicarboxylic acid. Is more preferably 1.5 molar equivalents or less, and preferably 1.3 molar equivalents or less.
  • an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
  • the compound (X) can be obtained by reacting the compound (X1) having a hydroxyl group with a strong base such as NaH and then reacting with an acid anhydride.
  • the amount of strong base such as NaH is usually 0.5 molar equivalents or more, preferably 0.8 molar equivalents or more, and usually 3 moles, based on the usage amount of compound (X1). It is preferably not more than the equivalent, preferably not more than 1.5 molar equivalent, more preferably not more than 1.3 molar equivalent.
  • an activator such as N, N-dimethyl-4-aminopyridine may be used in combination.
  • any one of the compounds represented by the general formulas (Y1) to (Y3) (hereinafter referred to as “compounds (Y1) to (Y3)”) and the compounds represented by the general formulas (Y4) to (Y6) (Hereinafter referred to as “compounds (Y4) to (Y6)”) to react with the compound represented by general formula (Y) (hereinafter referred to as “general formula (Y)”).
  • “-” extending from the inside of the ring represents a bond extending from any position of the ring.
  • Ax, Ay and Az each have the same meaning as described above, and preferred examples thereof are also the same as described above.
  • the compound represented by the following formula (I) ′′ is obtained by reacting the compound (X) obtained as described above with the compound (Y).
  • Ar, A 1 , A 2 , B 1 , B 2 , Y 1 , Y 2 , Y 3 , Y 4 , G 1 , G 2 , P 1 , P 2 , p, q are , Each having the same meaning as described above, and preferred examples thereof are also the same as described above.
  • the intermediate B synthesized in Step 2 2.50 g (6.77 mmol) and N-methyl-2-pyrrolidone: 100 mL were placed in a nitrogen stream. did. Thereto was added 13.49 g (37.21 mmol) of Intermediate C synthesized in Step 3 above. Next, 0.909 g (7.44 mmol) of N, N-dimethyl-4-aminopyridine was added. Subsequently, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride: 8.56 g (44.66 mmol) was added over 5 minutes while maintaining the internal temperature of the reaction solution at 20 ° C.
  • the structure of the target product was identified by 1 H-NMR.
  • a three-necked reactor equipped with a thermometer was charged with 4.1 g of sodium hydride (oil-based) (2.67 g (55.58 mmol) as pure sodium hydride) and 75 mL of THF in a nitrogen stream. It was set as the solution. Thereto was dissolved 13.35 g (50.53 mmol) of 4- (6-acryloyloxy-hex-1-yloxy) phenol (manufactured by DKSH) in 75 mL of THF and added as a solution.
  • the structure of the target product was identified by 1 H-NMR.
  • the substrate was placed on a hot plate, heated from 50 ° C. to 200 ° C., and then cooled again to 50 ° C. Changes in the structure of the structure when the temperature was raised or lowered were observed with a deflection optical microscope (Nikon Corporation, ECLIPSE LV100POL type).
  • the measured phase transition temperatures are shown in Table 1 below.
  • C represents Crystal
  • N represents Nematic
  • I represents Isotropic.
  • Crystal means that the test compound is in a solid phase
  • Nematic means that the test compound is in a nematic liquid crystal phase
  • Isotropic means that the test compound is in an isotropic liquid phase. Show. From Table 1, it can be seen that the polymerizable liquid crystal compounds 1 to 3 exhibit liquid crystallinity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polarising Elements (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal (AREA)

Abstract

La présente invention concerne un composé de cristaux liquides polymérisable qui présente une cristallinité liquide par lui-même, et qui est capable de former un corps optiquement anisotrope et un film optique qui ont une dispersion de longueur d'onde idéale présentant des propriétés de bande large, à savoir une dispersion de longueur d'onde inverse. Un composé de cristaux liquides polymérisable selon la présente invention est représenté par la formule (I). (Dans La formule (I), Ar représente un groupe qui est exprimé par l'une des formules (II-1)-(II-3).)
PCT/JP2019/017082 2018-04-27 2019-04-22 Composé de cristaux liquides polymérisable, composition de cristaux liquides polymérisable, polymère, film optique, corps optiquement anisotrope, plaque de polarisation, dispositif d'affichage et film antireflet WO2019208516A1 (fr)

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CN201980026401.5A CN111989317B (zh) 2018-04-27 2019-04-22 聚合性液晶化合物、聚合性液晶组合物、高分子、光学膜、光学各向异性体以及偏振片
KR1020207030013A KR20210004998A (ko) 2018-04-27 2019-04-22 중합성 액정 화합물, 중합성 액정 조성물, 고분자, 광학 필름, 광학 이방체, 편광판, 표시 장치, 그리고, 반사 방지 필름

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015025793A1 (fr) * 2013-08-22 2015-02-26 日本ゼオン株式会社 Composé polymérisable, composition polymérisable, polymère et corps optiquement anisotrope
WO2016088749A1 (fr) * 2014-12-04 2016-06-09 Dic株式会社 Composé polymérisable, composition, polymère, corps optiquement anisotrope, dispositif d'affichage à cristaux liquides et élément el organique
WO2016104317A1 (fr) * 2014-12-25 2016-06-30 Dic株式会社 Composé polymérisable et objet optiquement anisotrope
JP2016128403A (ja) * 2014-12-02 2016-07-14 Jnc株式会社 液晶性化合物、液晶組成物およびその重合体
WO2017098988A1 (fr) * 2015-12-08 2017-06-15 Dic株式会社 Composé polymérisable et corps optiquement anisotrope
WO2018101122A1 (fr) * 2016-11-29 2018-06-07 Dic株式会社 Composition polymérisable et corps optiquement anisotrope dans lequel celui-ci est utilisé
WO2018128084A1 (fr) * 2017-01-06 2018-07-12 Dic株式会社 Composé polymérisable et corps optiquement anisotrope

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015025793A1 (fr) * 2013-08-22 2015-02-26 日本ゼオン株式会社 Composé polymérisable, composition polymérisable, polymère et corps optiquement anisotrope
JP2016128403A (ja) * 2014-12-02 2016-07-14 Jnc株式会社 液晶性化合物、液晶組成物およびその重合体
WO2016088749A1 (fr) * 2014-12-04 2016-06-09 Dic株式会社 Composé polymérisable, composition, polymère, corps optiquement anisotrope, dispositif d'affichage à cristaux liquides et élément el organique
WO2016104317A1 (fr) * 2014-12-25 2016-06-30 Dic株式会社 Composé polymérisable et objet optiquement anisotrope
WO2017098988A1 (fr) * 2015-12-08 2017-06-15 Dic株式会社 Composé polymérisable et corps optiquement anisotrope
WO2018101122A1 (fr) * 2016-11-29 2018-06-07 Dic株式会社 Composition polymérisable et corps optiquement anisotrope dans lequel celui-ci est utilisé
WO2018128084A1 (fr) * 2017-01-06 2018-07-12 Dic株式会社 Composé polymérisable et corps optiquement anisotrope

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE REGISTRY [online] 15 August 2016 (2016-08-15), retrieved from STN Database accession no. RN 1973393- 05-3 *
OPENSHAW, H. T. ET AL.: "201. Strychnine and brucine. Part XLV. Synthetical experiments. Part III", JOURNAL OF THE CHEMICAL SOCIETY, 1946, pages 912 - 918, XP055646035 *

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