WO2020175394A1 - 光学層及び該光学層を含む積層体 - Google Patents

光学層及び該光学層を含む積層体 Download PDF

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WO2020175394A1
WO2020175394A1 PCT/JP2020/007180 JP2020007180W WO2020175394A1 WO 2020175394 A1 WO2020175394 A1 WO 2020175394A1 JP 2020007180 W JP2020007180 W JP 2020007180W WO 2020175394 A1 WO2020175394 A1 WO 2020175394A1
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group
compound
formula
ring
meth
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PCT/JP2020/007180
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English (en)
French (fr)
Japanese (ja)
Inventor
悠司 淺津
昭一 小澤
亜依 小橋
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住友化学株式会社
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Priority to CN202080017096.6A priority Critical patent/CN113474688B/zh
Priority to KR1020217028875A priority patent/KR20210134341A/ko
Publication of WO2020175394A1 publication Critical patent/WO2020175394A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/372—Sulfides, e.g. R-(S)x-R'
    • C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/378—Thiols containing heterocyclic rings
    • 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
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133528—Polarisers
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/50—OLEDs integrated with light modulating elements, e.g. with electrochromic elements, photochromic elements or liquid crystal elements
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light

Definitions

  • the present invention relates to an optical layer and a laminate including the optical layer.
  • Display devices such as organic light !_ display devices and liquid crystal display devices (? 0: flat panel displays) include various organic light display devices such as organic light !_ devices, liquid crystal cell display devices and optical films such as polarizing plates. Various members are used. As organic compounds and liquid crystal compounds used for these materials, compounds with weak weather resistance are often used among organic substances, so that not only ultraviolet rays (II V) but also wavelengths of 380 to 420 Degradation due to visible light with a short wavelength of n 01 or less is likely to be a problem. In order to solve such a problem, for example, Patent Document 1 describes an optical layered body provided with an adhesive layer containing a compound represented by the following formula.
  • Patent Document 1 Japanese Patent Laid-Open No. 2 017 7-4 8340
  • the present invention includes the following inventions. ⁇ 0 2020/175 394 2 (:171? 2020/007180
  • Carboxy group one 3 5 One 3 3 3 One 3_Rei 3 1-1, One 3_Rei 2 1-1, aliphatic hydrocarbon group which has good carbon atoms 1 to be 2 5 substituted or substituted Represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a group, and is included in the aliphatic hydrocarbon group or aromatic hydrocarbon group.
  • the compound having a molecular weight of 300 or less and having a partial structure represented by the formula (X) is a compound represented by the formula ( ⁇ ) to a compound represented by the formula (VIII).
  • ring ⁇ / 12 each independently represent a ring structure having at least one double bond as a component of the ring.
  • Each 13 independently represents a ring having at least one nitrogen atom as a constituent element.
  • [3 ⁇ 4 1 13 are each independently, a heterocyclic group, a halogen atom, a nitro group, a cyano group, hydroxy group, thiol group, carboxyl group, one 3 5
  • One 3 3_Rei 3 1-1, - 30 ⁇ represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, Included in aromatic hydrocarbon groups or aromatic hydrocarbon groups Or _ ⁇ !!
  • 3_Rei 2 - may be substituted with.
  • 6 2 and 63 may be bonded to each other to form a ring.
  • [3 ⁇ 4 9 and [ ⁇ ⁇ each independently represent a trivalent linking group.
  • [Four] At least one selected from a nitro group, a cyano group, full Tsu atom, a chlorine atom, one hundred 3, One 3_Rei 3, fluoroalkyl group, one hundred - ⁇ - [3 ⁇ 4 2 2 2 or - 3_Rei 2 —[3 ⁇ 4 2 2 2 ([ ⁇ 2 2 2 is a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms or an optionally substituted carbon group 6 to 6 Represents an aromatic hydrocarbon group of 18.
  • optical layer according to [2] or [3].
  • At least one selected from is a cyano group [2]
  • optical layer according to any one of [5].
  • a cyano group, _ ⁇ _ _ _ _ [3 ⁇ 4 2 2 2 or 1 3 0 2 _ [3 ⁇ 4 2 2 2 2 2 2 is a hydrogen atom, or a C 1 -C 25 that may have a substituent. It represents an alkyl group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. )
  • the optical layer according to any one of [2] to [6].
  • optical layers according to any one of [2] to [8], each of which is independently an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • optical layer according to any one of [1] to [18], which is formed from a composition containing a crosslinking agent.
  • optical layer according to any one of [1] to [18], which is formed from a composition containing a photopolymerization initiator.
  • [2 1] A compound having a molecular weight of 300 or less and having a partial structure represented by the formula (X), and a composition containing at least one resin selected from the following group [1] ⁇
  • Group 8 Cellulose resin, (meth)acrylic resin, polyester resin, polyamide resin, polyimide resin and cycloolefin resin
  • An optical layered body including the optical layer according to any one of [1] to [21] and a polarizer.
  • a composition comprising a cross-linking agent.
  • a composition containing a photopolymerization initiator A composition containing a photopolymerization initiator.
  • a composition comprising a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X), and at least one resin selected from the following group.
  • Group 8 Cellulose resin, (meth)acrylic resin, polyester resin, polyamide resin, polyimide resin and cycloolefin resin
  • the present invention provides an optical layer having good weather resistance.
  • FIG. 1 A schematic cross-sectional view schematically showing an example of the optical laminate of the present invention.
  • FIG. 2 is a schematic cross-sectional view schematically showing an example of the optical layered body of the present invention.
  • FIG. 3 is a schematic sectional view schematically showing an example of the optical layered body of the present invention.
  • FIG. 4 is a schematic sectional view schematically showing an example of the optical layered body of the present invention.
  • FIG. 5 is a schematic sectional view schematically showing an example of the optical layered body of the present invention.
  • FIG. 6 is a schematic cross-sectional view schematically showing an example of the optical layered body of the present invention.
  • the "(meth)acryloyl group” means at least one selected from an acryloyl group and a methacryloyl group.
  • the optical layer of the present invention is a layer that absorbs and/or transmits light.
  • the optical layer may be a layer included in an optical member such as a display device or an image pickup device.
  • the optical layer of the present invention has a high absorptivity for visible light having a short wavelength near 395 1 ⁇ , while having a low absorptivity for light near a wavelength of 430 n, which suppresses the influence on the hue of a display device. can do.
  • the optical layer of the present invention includes a compound having a molecular weight of 300 or less and having a partial structure represented by the formula (X) (hereinafter sometimes referred to as compound (X)). ⁇ 0 2020/175394 13 (: 17 2020/007180
  • optical layer of the present invention preferably satisfies the following formula (3).
  • the value of (395) is preferably at least 0.6, more preferably at least 0.8, and particularly preferably at least 1.0 from the viewpoint of suppressing weathering deterioration. There is no upper limit, but it is usually less than 10.0.
  • optical layer of the present invention more preferably satisfies the following formula (distance).
  • the value of eight (3 9 5) / eight (4 3 0) is The ratio of the size of the light absorption at the wavelength of 395 n to the size of the light absorption of is shown, and the larger this value is, the more specific absorption is in the wavelength region near 395 n. It is possible to suppress the influence of hue on the image.
  • the value of eight (3 95)/eight (4 30) is preferably 15 or more, more preferably 20 or more, and particularly preferably 30 or more.
  • the thickness of the optical layer of the present invention is usually 1 to 500, and preferably 2 to 1
  • 0 more preferably 2.5 to 50, and further preferably 3 to 30.
  • Examples of the optical layer of the present invention include a polarizer, a protective film, and a retardation film. ⁇ 0 2020/175394 14 ⁇ (: 171? 2020 /007180
  • the optical layer of the present invention can be obtained, for example, by molding a composition containing the compound (X) into a sheet. Further, another optical layer may be laminated on the optical layer of the present invention to form an optical laminate. When the optical layers are laminated, the optical layers of the present invention may be laminated, or the optical layer of the present invention and a layer containing no compound (X) may be laminated.
  • the optical layer of the present invention contains a compound having a molecular weight of 300 or less and having a partial structure represented by the formula (X).
  • the ring is not particularly limited as long as it is a ring having one or more double bonds as a constituent element of the ring and does not have aromaticity. May be a monocycle or may be a condensed ring.
  • a hetero atom for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.
  • the double bond contained in is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
  • it is a ring having 5 to 18 carbon atoms, preferably a 5 to 7-membered ring structure, and more preferably a 6-membered ring structure.
  • [0018] may have a substituent.
  • substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and the like.
  • C1-C12 alkyl group fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1, 1,2,2-Tetrafluoroethyl group, 1,1,2,2,2-Pentafluoroethyl group and other halogenated alkyl groups having 1 to 12 carbon atoms; methoxy group, ethoxy group, propoxy group An alkoxy group having 1 to 12 carbon atoms such as a butoxy group, a pentyloxy group and a hexyloxy group; a methylthio group, an ethylthio group, a propylthio group, a butyl group ⁇ 0 2020/175394 16 ⁇ (: 171? 2020/007180
  • Alkyl groups having 1 to 12 carbon atoms such as thio group, pentylthio group and hexylthio group; monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1, 1, 2, 2, 2 -Fluorinated alkoxy groups having 1 to 12 carbon atoms such as pentafluoroethoxy group; alkyl groups having 1 to 6 carbon atoms such as amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group and methylethyl group An amino group which may be substituted with; an alkylcarbonyloxy group having 2 to 12 carbon atoms such as a methylcarbonyloxy group and an ethylcarbonyloxy group; a carbon number 1 to 12 such as a methylsulfonyl group and an ethylsulfonyl group off We sulfon
  • the substituent which may have is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms or 1 to 12 carbon atoms.
  • It is preferably an amino group which may be substituted with an alkyl group of 6.
  • *1 represents a bond with a nitrogen atom
  • *2 represents a bond with a carbon atom
  • the heterocyclic group represented by [0021] includes a pyridyl group, a pyrrolidyl group, a tetrahydrofurfuryl group, a tetrahydrothiophene group, a pyrrole group, a furyl group, a thiopheno group, a piperidine group, a tetrahydropyranyl group, and tetrahydrothio.
  • Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by 3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a closed butyl group, and a 6 "1:-butyl group.
  • the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by 3 is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms. ..
  • aliphatic hydrocarbon group substituents which may be possessed represented, halo gen atom, a hydroxyl group, a nitro group, a cyano group, and one 3_Rei 3 1-1 like.
  • 1-1 2 _ also contained in the aliphatic hydrocarbon group with carbon number 1-2 5 represented by 3 ⁇ 02020/175394 20 units (: 171? 2020 /007180
  • the aliphatic hydrocarbon group is represented by _ ⁇ _[3 ⁇ 4'([3 ⁇ 4' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom) It is preferably an alkoxy group. It may also be a polyalkyleneoxy group such as a polyethyleneoxy group or a polypropyleneoxy group. 101 In the alkoxy group represented, for example, main butoxy group, an ethoxy group, and the like one hundred 3 group.
  • the aliphatic hydrocarbon group is Is preferably an alkylthio group represented by (C1-24 alkyl group which may have a halogen atom). It may also be a polyalkylenethio group such as a polyethylenethio group or a polypropylenethio group.
  • alkylthio groups table with ', e.g., methylthio group, ethylthio group, One 3_Rei 3 group, polyethylene thio group, polypropylene thio group and the like. Included in the aliphatic hydrocarbon group having 1 to 25 carbon atoms
  • the aliphatic hydrocarbon group is __[3 ⁇ 4' ([3 ⁇ 4, is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom. is preferably a group represented by) one 3_Rei 2 ⁇ ! ⁇ 1 2 group, one 3_Rei 2 ⁇ ! ⁇ 1 2 group, etc. ⁇ 02020/175394 21 21 (:171? 2020/007180
  • [3 ⁇ 4 is preferably a group represented by an alkyl group having 1 to 24 carbon atoms which may have a halogen atom).
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by 1 1 18 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 6 "1:-butyl group, a 36 _ butyl group, Pentyl group, Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms such as a hexyl group and a 1-methylbutyl group.
  • Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by are phenyl group, naphthyl group, anthracenyl group, tetracenyl group, pentacenyl group, phenanthryl group, chrysenyl group, triphenylenyl group, tetraphenyl group, An aryl group having 6 to 18 carbon atoms such as a pyrenyl group, a perylenyl group, a coronenyl group and a biphenyl group; an aralkyl group having a carbon number of 7 to 18 such as a benzyl group, a phenylethyl group and a naphthylmethyl group. It is preferably an aryl group of the number 6 to 18 and more preferably a phenyl group or a benzyl group.
  • the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by may have: a halogen atom; a hydroxyl group; a thiol group; an amino group; a nitro group; a cyano group; ⁇ 3 1 to 1 group and the like can be mentioned.
  • the aromatic hydrocarbon group is an aryloxy group having a carbon number of 6 to 17 such as a phenoxy group; a phenoxyethyl group, a phenoxydiethylene glycol group, an arylalcohol of a phenoxypolyalkylene glycol group. It is preferably a Coxy group or the like.
  • the aromatic hydrocarbon group is represented by _ 3 0 2 _ 8” (is an aryl group having 6 to 17 carbon atoms or an aralkyl group having 7 to 17 carbon atoms). It is preferable that it is a group represented by.
  • halogen atom represented by are fluorine atom, chlorine atom, bromine atom, iodine atom and the like.
  • the molecular weight of the compound (X) is preferably 250 or less, more preferably 200 or less, still more preferably 150 or less, and particularly preferably 10 or less. 0 or less. ⁇ 0 2020/175394 23 ⁇ (: 17 2020/007180
  • the compound (X) may be a cobolimer as long as it has a molecular weight of 300 or less. It is preferably a monomer.
  • Compound (X) is wavelength 3 7 0 n or 4 2 0 n indicate Succoth the maximum absorption wavelength below are preferred.
  • the maximum absorption wavelength (S 013) of compound (X) is preferably the wavelength The wavelength is m or less, more preferably 375 n or more and 410 n or less, and further preferably 380 1 ⁇ ⁇ ! or more and 4 0 0 1 ⁇ ⁇ ! or less.
  • the compound (X) preferably has a gram extinction coefficient ⁇ in the s 1113 of at least 0.5, more preferably at least 0.75, and particularly preferably at least 1.0.
  • the upper limit is not particularly limited, but is generally 10 or less.
  • S 1113 represents the maximum absorption wavelength of compound (X).
  • the UV to near-UV light in the wavelength range of 380 to 400! Can be absorbed efficiently.
  • £ (Su 1113)/£ (Su 1113 + 3011111) is 5 or more, preferably 10 or more, and particularly preferably 20 or more.
  • the upper limit is not particularly limited, but is generally 100 or less.
  • £ (Su 1113) is the gram extinction coefficient at the maximum absorption wavelength [ ⁇ 0!] of Compound (X)
  • £ (Su 1113 + 3 ⁇ 11 111) is the (Max absorption wavelength of Compound (X). It represents the Gram extinction coefficient at the wavelength of [1 ⁇ 111] + 3 0 11 111).
  • the compound (X) may be a compound represented by the formula () or a compound represented by the formula (VIII). ⁇ 0 2020/175 394 24 (: 17 2020/007180
  • the compound represented by the formula () is more preferable.
  • ring ⁇ / 12 each independently represent a ring structure having at least one double bond as a component of the ring.
  • Each 13 independently represents a ring having at least one nitrogen atom as a constituent element.
  • [3 ⁇ 4 1 13 are each independently, a heterocyclic group, a halogen atom, a nitro group, a cyano group, hydroxy group, thiol group, carboxyl group, one 3 5
  • One 3 3_Rei 3 1-1, - 30 ⁇ represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, Included in aromatic hydrocarbon groups or aromatic hydrocarbon groups Or _ ⁇ !!
  • 3_Rei 2 - may be substituted with.
  • Ring 2 Ring ⁇ / ⁇ /3, Ring ⁇ / ⁇ /4, Ring ⁇ / ⁇ /5, Ring ⁇ / ⁇ /6, Ring ⁇ / ⁇ / 7 , Ring ⁇ / ⁇ / 8 , Ring 9 , Ring ⁇ / ⁇ / 1 ⁇ , ring and ring
  • Ring 2 to ring may be a single ring or a condensed ring.
  • a hetero atom eg, oxygen atom, sulfur atom, nitrogen atom, etc.
  • the compound has at least one double bond as a ring constituent, but the double bonds contained in ring 2 to ring ⁇ / 12 are each independently 1 to 4 and usually 1 to 3. Is preferred, 1 or 2 is more preferred, and 1 is even more preferred.
  • the ring ⁇ / ⁇ / 2 to the ring ⁇ 12 are each independently a ring having 5 to 18 carbon atoms,
  • a 5- to 7-membered ring structure is preferable, and a 6-membered ring structure is more preferable.
  • each independently represents a monocycle. Further, it is preferable that each of ring 2 to ring 12 is independently a ring having no aromaticity. May have a substituent. Examples of the substituent include the same substituents that ring 1 may have.
  • the substituents that the ring ⁇ / ⁇ / 2 to the ring ⁇ 12 may have include an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and a carbon number It is preferably an alkylthio group having 1 to 12 or an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms.
  • a monocycle may be used or a condensed ring may be used, but a monocycle is preferable.
  • Examples of the group include a hydroxyl group; a thiol group; an aldehyde group; a methyl group, an ethyl group, etc. ⁇ 02020/175394 29 ⁇ (: 171? 2020 /007180
  • alkyl group having 1 to 6 carbon atoms an alkoxy group having 1 to 6 carbon atoms such as methoxy group and ethoxy group; an alkylthio group having 1 to 6 carbon atoms such as methylthio group and ethylthio group; amino group, methylamino group, Carbon such as dimethylamino group and methylethyl
  • a hydrogen atom or an alkyl group having 1 to 6 carbon atoms Represents an alkyl group having 1 to 6 carbon atoms. ) ; ⁇ 33 [3 ⁇ 4 4 dried (?3 ⁇ 4 4 represents an alkyl group having 1 to 6 carbon atoms.) ; 1030 [3 ⁇ 4 5 dried represents an alkyl group having 1 to 6 carbon atoms. ); _S ⁇ 2 R 6 f (R 5 f represents an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms which may have a fluorine atom), and the like.
  • Each 13 is independently a ring containing one nitrogen atom as a ring constituent.
  • Each 13 may independently be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring.
  • Each of them is independently a 5- to 10-membered ring, preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring.
  • ⁇ 02020/175394 30 box (: 171? 2020 /007180 It may have a substituent. Examples of the substituent that the ring 112 and the ring 113 may have are the same as the substituents of.
  • X 1 is _ 0 ⁇ _ , _ 0 ⁇ ⁇ _ , _ ⁇ ⁇ 0 _ , — 03 — % — 033 — % — 0 03-, -030-,-3 0 2 -, 1 223 ⁇ 001 or Represents 100 224 -.
  • 8 222 represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent.
  • [3 ⁇ 4 223 and [3 ⁇ 4 224 are each independently a hydrogen atom and an alkyl group having 1 to 6 carbon atoms. ⁇ 0 2020/175394 31 ⁇ (: 171? 2020 /007180
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • halogenated alkyl group examples include a trifluoromethyl group, a bellofluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro 3 ⁇ ⁇ -butyl group, a perfluoro ⁇ “-butyl group, a perfluoropentyl group and a perfluorohexyl group.
  • a perfluoroalkyl group is preferable, and a halogenated alkyl group usually has 1 to 25 carbon atoms, and preferably has 1 to 12 carbon atoms.
  • the halogenated alkyl group may be linear or branched.
  • halogenated aryl group examples include a fluorophenyl group, a chlorophenyl group, a bromophenyl group and the like, preferably a fluoroaryl group, and more preferably a perfluoroaryl group.
  • the aryl group containing a halogen atom has usually 6 to 18 carbon atoms, preferably 6 to 18 carbon atoms.
  • X 1 is ten thousand and one or one 3_Rei 2 - is preferably.
  • Examples of the alkyl group having 1 to 25 carbon atoms represented by 3 ⁇ 4 2 2 2 include a methyl group, an ethyl group, a _propyl group, an isopropyl group, a _butyl group, a 6 ⁇ 1: _butyl group, 3 ⁇ — Butyl group, Pentyl group, Examples thereof include linear or branched alkyl groups having 1 to 25 carbon atoms such as hexyl group, 1-methylbutyl group, 3-methylbutyl group, —octyl group, —decyl, and 2-hexyloctyl group.
  • 2 2 2 2 is preferably alkyl having 1 to 12 carbon atoms.
  • Examples of the optionally substituted substituent include a halogen atom and a hydroxy group.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by 3 ⁇ 4 2 22 includes an aryl group having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group. ⁇ 02020/175394 32 ⁇ (: 171? 2020 /007180
  • substituents examples include a halogen atom and a hydroxy group.
  • the ring formed by combining may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring. Further, the ring formed by combining with each other may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a constituent element of the ring.
  • the ring formed by and are usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.
  • Examples of the ring formed by and are bonded to each other include the structures described below.
  • the ring formed by is a substituent (in the above formula,
  • the substituent is, for example, The same as the substituent which may have.
  • the above [3 ⁇ 4 1 £ to [3 ⁇ 4 16 £ are each independently preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and further preferably Is a methyl group.
  • a pyrrolidyl group Piberiji group, tetrahydrofurfuryl group, tetrahydropyranyl group, tetrahydro Chiofueno group, tetrahydrothiopyranyl group, or a pyridyl group Is preferred.
  • the aliphatic hydrocarbon group having 1 to 25 carbon atoms is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms.
  • Examples of the substituent which may group optionally having a halogen atom, a hydroxyl group, a nitro group, a cyano group, and one 3_Rei 3 1-1 like.
  • ⁇ ⁇ 02020/175394 35 ⁇ (:? 171 2020/007180 3 , [3 ⁇ 4 23, [3 ⁇ 4 33, [3 ⁇ 4 43, [3 ⁇ 4 53, [3 ⁇ 4 63, [3 ⁇ 4 73, [3 ⁇ 4 83, [3 ⁇ 4 93, [3 ⁇ 4 103 and
  • the aliphatic hydrocarbon group is represented by _ ⁇ _[3 ⁇ 4'([3 ⁇ 4' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom) It is preferably an alkoxy group. It may also be a polyalkyleneoxy group such as a polyethyleneoxy group or a polypropyleneoxy group. 101 In the alkoxy group represented, for example, main butoxy group, an ethoxy group, and the like one hundred 3 group.
  • the aliphatic hydrocarbon group is Is preferably an alkylthio group represented by (C1-24 alkyl group which may have a halogen atom). It may also be a polyalkylenethio group such as a polyethylenethio group or a polypropylenethio group.
  • alkylthio groups table with ', e.g., methylthio group, ethylthio group, One 3_Rei 3 group, polyethylene thio group, polypropylene thio group and the like. Included in the aliphatic hydrocarbon group having 1 to 25 carbon atoms
  • the aliphatic hydrocarbon group is __[3 ⁇ 4' ⁇ 02020/175394 36 ⁇ (: 171?2020/007180
  • [3 ⁇ 4, is preferably a group which is table with an alkyl group) of optionally carbon atoms, which may 1-24 a halogen atom, _3_Rei 2 Rei_1 ⁇ 1 2 group, _3_Rei 2 Rei_1 ⁇ 1 It may be two or the like. And are the same as the alkyl groups having 1 to 6 carbon atoms represented by.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by 103 and 13 has a carbon number represented by 8 3]
  • the same as the aromatic hydrocarbon group represented by 6 to 18 can be mentioned, and it is preferably an aryl group having 6 to 18 carbon atoms, more preferably a phenyl group or a benzyl group.
  • aromatic hydrocarbon group substituents which may be possessed by the carbon number of 6-1 8, a halogen atom, a hydroxyl group, a thiol group, an amino group, a nitro group, a cyano group; -3_Rei 3 1-1 radicals Etc.
  • Aromatic _ ⁇ _1 contained in the hydrocarbon group and 1 2 - or _ ⁇ ! is -30 2 -, one hundred one, one hundred and one, ten thousand and one, ten thousand and one, one hundred [3 ⁇ 4 13 eighty-one one [3 ⁇ 4 14 eighty-one thousand and one one 3-one It may be replaced with 3 01, 10 2 — or 10 1 to 1 —.
  • Is 10! is 101, 13—, 1001, 1001, 101 ⁇ 02020/175394 37 ⁇ (: 171? 2020/007180
  • _ ⁇ _1 ⁇ 1 2 included in the aromatic hydrocarbon group with carbon number 6-1 8 is preferably substituted with ..
  • [3 ⁇ 4 1 2 eight, as the [3 ⁇ 41 3 eight and [3 ⁇ 41 4 carbon atoms represented by ⁇ 6 alkyl group include those described above.
  • a condensed ring is formed by the ring formed by connecting and and V.
  • a ring formed by connecting 8 3 Specific examples of the condensed ring formed by and include the ring structures described below. ⁇ 02020/175394 38 ⁇ (: 171? 2020 /007180
  • the double bond forming Ring 2 is included as a constituent element of the ring formed. That is,
  • a ring formed by combining 12 and 13 with each other and Ring 2 form a condensed ring.
  • a ring formed by linking and The same thing as the condensed ring formed by is mentioned.
  • the double bond forming ring 6 is included as a component of the ring formed. That is,
  • a ring formed by combining 52 and 53 and ring 6 forms a condensed ring.
  • a ring formed by linking and The same thing as the condensed ring formed by is mentioned.
  • a ring formed by combining 62 and 63 and ring 7 forms a condensed ring.
  • a ring formed by linking and The same thing as the condensed ring formed by is mentioned.
  • the double bond forming the ring 9 is included as a component of the ring formed. That is,
  • a ring formed by combining 82 and 83 with each other and ring 9 form a condensed ring.
  • a ring formed by linking and The same thing as the condensed ring formed by is mentioned.
  • the ring formed by and being bonded to each other contains one nitrogen atom as a constituent element of the ring.
  • the ring formed by combining 2 and 2 may be a monocycle or a condensed ring, but is preferably a monocycle.
  • the ring formed by combining 1 and 2 with each other may further contain a hetero atom (oxygen atom, sulfur atom, nitrogen atom, etc.) as a constituent element of the ring.
  • the ring formed by combining 2 and 2 with each other is ⁇ 0 2020/175 394 40 ⁇ (: 171? 2020 /007180
  • An aliphatic ring is preferable, and an aliphatic ring having no unsaturated bond is more preferable.
  • the ring formed by and are usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.
  • the ring formed by combining 1 and 2 with each other may have a substituent, and examples thereof include the same substituents that ring 2 to ring 12 may have.
  • Examples of the ring formed by combining and with each other include the rings described below.
  • [3 ⁇ 4 4 1 and 2 are bonded to each other to form a ring, The same as the ring formed by combining with each other.
  • the divalent linking group is a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a carbon number 6 to 1 which may have a substituent. 8 represents a divalent aromatic hydrocarbon group.
  • examples of the substituent that the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group and the like.
  • the divalent linking groups are preferably each independently a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent. More preferably, it is a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may be present.
  • divalent linking group examples include the following linking groups.
  • * represents a bond.
  • a divalent aliphatic hydrocarbon group having 18 carbon atoms or a linking group represented by the following formula is preferable, and a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent.
  • a hydrogen group or a linking group represented by the following formula is more preferable. ⁇ 0 2020/175394 46 ⁇ (: 171? 2020 /007180
  • [0072] is preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may have a substituent, or a linking group represented by the following formula.
  • the trivalent linking groups represented by 9 and are each independently a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or a substituent which may have a substituent. Examples thereof include a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be possessed.
  • 6 represents an alkyl group. ) May be replaced.
  • Examples of the substituent that the trivalent aliphatic hydrocarbon group and the trivalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, and an amino group.
  • Trivalent linking group represented 9 and in each independently, it is not preferable is a trivalent aliphatic hydrocarbon group which has good carbon atoms 1 to be 1 2 have a substituent.
  • Examples of the trivalent linking group represented include linking groups described below. ⁇ 0 2020/175394 47 ⁇ (: 171? 2020 /007180
  • Examples thereof include a tetravalent aliphatic hydrocarbon group having 1 to 18 or a tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent.
  • _ ⁇ 1-1 2 _ (yo included in the tetravalent aliphatic hydrocarbon 3 ⁇ 4, _ ⁇ _, - 3% - 0 3% _ ⁇ _ ⁇ _, -3 0, Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ) May be replaced.
  • Examples of the substituent that the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, and an amino group.
  • each independently a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may have a substituent.
  • [0075] is preferably an alkyl group having 1 to 15 carbon atoms
  • 8 2 is preferably an alkyl group of 1 to 1 5 carbon atoms, 1
  • 1 and 2 are preferably linked to each other to form a ring, more preferably an aliphatic ring, more preferably an aliphatic ring having no unsaturated bond, and a pyrrolidine ring.
  • a piperidine ring structure it is particularly preferable to have a piperidine ring structure.
  • Nitro group a cyano group, a halogen atom, one hundred 3, One 3_Rei 3, 5, One 3 3, a fluoroalkyl group (preferably, 1-2 5 carbon atoms), a full Oroariru group (preferably 6 carbon atoms ⁇ 18), _ ⁇ ⁇ _ ⁇ _ [3 ⁇ 4 1 1 ⁇ or
  • ⁇ 02020/175394 50 50 (:171? 2020/007180
  • Particularly preferred is a cyano group.
  • Both are preferably cyano groups.
  • [3 ⁇ 4 61 , [3 ⁇ 4 91 , [3 ⁇ 4 10 1 and [3 ⁇ 4 111] are each independently preferably an alkyl group having 1 to 15 carbon atoms, and preferably an alkyl group having 1 to 10 carbon atoms. More preferable.
  • ⁇ 12, ⁇ 42, ⁇ 52, ⁇ 62, ⁇ 72, ⁇ 82, ⁇ 92, [3 ⁇ 4102 and ⁇ 112 are each independently preferably an alkyl group having 1 to 15 carbon atoms. More preferably, it is an alkyl group having 1 to 10 carbon atoms.
  • ring are preferably linked to each other to form a ring, more preferably to form an aliphatic ring, more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or piperidine. It preferably has a ring structure.
  • ring are preferably linked to each other to form a ring, more preferably to form an aliphatic ring, more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or piperidine. It preferably has a ring structure.
  • ring are preferably linked to each other to form a ring, more preferably to form an aliphatic ring, more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or piperidine. It preferably has a ring structure.
  • a ring more preferably an aliphatic ring, further preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or piperidine. It preferably has a ring structure.
  • [3 ⁇ 4 1 12 are preferably linked to each other to form a ring, more preferably form an aliphatic ring, further preferably an aliphatic ring having no unsaturated bond, particularly preferably Preferably has a pyrrolidine ring or piperidine ring structure.
  • [3 ⁇ 4 1 13 are each independently a nitro group; a cyano group; a halogen atom ; 1003 ; _30 3; _3 5 ;_3 3; a fluoroalkyl group having 1 to 25 carbon atoms; 8 fluoroaryl groups;
  • 1 12/ ⁇ 12's each independently represent an alkyl group having 1 to 24 carbon atoms, which may have a halogen atom. ) Is preferred, and a cyano group; a fluorine atom; a chlorine atom; 1003 ; — 3030 ; a fluoroalkyl group having 1 to 12 carbon atoms.
  • Particularly preferred is a cyano group.
  • [3 ⁇ 415, [3 ⁇ 425, [3 ⁇ 435, [3 ⁇ 475 and [ ⁇ 85 are each independently a nitro group, a cyano group, a halogen atom, 10000 3 , 1 3 03, 1 3 5 and 1 3 5 3 , 100 ⁇ — ⁇ _ [3 ⁇ 4 222, _3 ⁇ 2 _ [3 ⁇ 4 222 ([ ⁇ 222 represents an alkyl group having 1 to 25 carbon atoms which may have a halogen atom), 1 carbon number preferably - a fluoroalkyl group or a fluoroaryl group with carbon number 6-1 eighth 25, nitro group, cyano group, fluorine atom, chlorine atom, _ ⁇ _ ⁇ 3, one 3_Rei 3, full ⁇ 02020/175394 52 ⁇ (: 171? 2020/007180
  • Fluoroalkyl group _ ⁇ _ ⁇ _ ⁇ _ [3 ⁇ 4 222 or one 3_Rei 2 _ [3 ⁇ 4 222 ([3 ⁇ 4 222 represents an alkyl group of halo gen atom good carbon atoms which may have from 1 to 25) it is More preferred,
  • Particularly preferred is a cyano group.
  • 35] have the same structure.
  • [ 74] and [ 75] preferably have the same structure.
  • the compound represented by the formula ([) is a compound represented by the formula ([_1]), a compound represented by the formula ([_2]) or a compound represented by the formula ([3]). Is more preferable.
  • 0! 1 represents an integer from 0 to 4
  • 012 represents an integer from 0 to 5.
  • each is independently 0 or 1.
  • the compound represented by the formula ( ⁇ ) is a compound represented by the formula ( ⁇ _8) ⁇ 02020/175394 53 ⁇ (: 17 2020 /007180
  • 8x9, 8x1. , 8x11 and 8x12 each independently represent a hydrogen atom or a substituent. ]
  • the compound represented by the formula (IIII) is preferably a compound represented by the formula ( ⁇ _8).
  • 8x13, 8x14, ⁇ > ⁇ 15 and ⁇ > ⁇ 16 each independently represent a hydrogen atom or a substituent.
  • substituents examples include the same substituents that ring 1 may have.
  • Examples of the compound represented by the formula (I) include the compounds described below.
  • the compound ( ⁇ ) is represented by formula (1 — 1) to formula (1 — 4), formula (1 _7), formula (1 — 8), formula (1 — 1 0), formula (1 — 1 2), formula (1 —20) ⁇ Expression (1 —25), Expression (1 —54) ⁇ Expression (1 —57), Expression (1 —59), Expression (1 —63) ⁇ Expression (1 —68), Expression (1 —68) 1 —70) ⁇ Formula (1 —78), Formula (1 —80), Formula (1 ⁇ 02020/175394 54 ⁇ (: 17 2020 /007180
  • a compound represented by the formula (II) (hereinafter sometimes referred to as compound (II)).
  • Examples of the compound include the compounds described below.
  • Examples of the compound represented by the formula ( ⁇ ) include the compounds described below.
  • Examples of the compound represented by the formula (V) include the compounds described below. ⁇ 02020/175394 71 ⁇ (: 171? 2020/007180
  • Examples of the compound represented by the formula (V) include the compounds described below.
  • the compound (V) includes formula (5-1) to formula (5-3), formula (5-6), formula (5-7), formula (5-9), formula (5-15), Formula (5-21), Formula (5-23), Formula (5-25), Formula (5-26), Formula (5-32), Formula (5-36), Formula (5-38)
  • the compound represented by formula (5-1) to formula (5-3), formula (5-21), formula (5-25), formula (5-36) is preferred. More preferably, it is a compound.
  • a compound represented by the formula (V I) (hereinafter sometimes referred to as compound (V I)).
  • Examples of the compound include the compounds described below.
  • the compound examples include the compounds described below. ⁇ 02020/175394 88 (: 17 2020 /007180) As the compound (VII), the formula (7-1) to the formula (7-9), the formula (7-12), the formula (7-14), The compounds represented by formula (7-17), formula (7-42) to formula (7-44) and formula (7-57) are preferable, and formula (7-1) to formula (7 -) 8), more preferably a compound represented by.
  • Examples of the compound represented by the formula (V I I I) include the compounds described below.
  • Examples of the compound (VIII) include formula (8-1), formula (8-2), formula (8-4), formula (8_5), formula (8_1 1), formula (8_1 3) to formula (8_). 1 7), Formula (8-25), Formula (8-26), Formula (8-47), Formula (8-48) ⁇ 02020/175394 96 ⁇ (: 17 2020/007180
  • the compound () is, for example, a compound represented by the formula (1) (hereinafter, compound ⁇ 0 2020/175394 106 ⁇ (: 171? 2020/007180
  • reaction between the compound (I-1) and the compound ( ⁇ 1-2) is usually carried out by mixing the compound (1-1) and the compound (__1), and It is preferable to add the compound ( ⁇ -2) to
  • the compound (I -2) and the base are mixed with the mixture of the compound (1 _ 1) and the methylating agent,
  • Examples of the base include metal hydroxides such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, calcium hydroxide, barium hydroxide, and magnesium oxide (preferably alkali metal water). Oxides); Metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium tert-butoxide; lithium hydride, hydrogen Sodium chloride, water ⁇ 0 2020/175394 107 ⁇ (: 171? 2020/007180
  • Metal hydrides such as potassium hydride, lithium aluminum hydride, sodium borohydride, aluminum hydride, sodium aluminum hydride; metal oxides such as calcium oxide and magnesium oxide; sodium hydrogen carbonate, sodium carbonate, potassium carbonate, etc.
  • Metal carbonates preferably alkaline earth metal carbonates); organic alkyl metal compounds such as normalptyllithium, evening butyllithium, methyllithium and Grignard reagents; ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidi Amine, piperidine, diazabicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, dimethoxyaniline, ammonium acetate, /3-alanine, etc.
  • Amine compounds preferably tertiary amines such as triethylamine and diisopropylethylamine
  • Metal amide compounds preferably alkali metal amides
  • Hydroxylation Examples thereof include sulfonium compounds such as trimethylsulfonium; iodonium compounds such as diphenyl iodonium hydroxide; and phosphazene bases.
  • the amount of the base used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, per 1 mol of the compound (_ 1).
  • methylating agent examples include iodomethane, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl paratoluenesulfonate, methyl trifluoromethanesulfonate, trimethyloxonium tetrafluoroborate and the like.
  • the amount of the methylating agent used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, per 1 mol of the compound (_ 1).
  • the reaction between the compound (I_1) and the compound (I_2) may be carried out in the presence of a solvent.
  • Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, 6 1 ⁇ 1: _butanol, 2-butano. ⁇ 0 2020/175394 108 ⁇ (: 171? 2020 /007180
  • 1 ⁇ 1-dimethylacetamide, 1 ⁇ 1, 1 ⁇ 1-dimethylformamide, water, etc. may be mentioned.
  • Acetonitrile, tetrahydrofuran, chloroform, dichloromethane and diethyl ether are preferable, acetonitril, tetrahydrofuran and chloroform are more preferable, and acetnitrile is more preferable.
  • the solvent is preferably a dehydrated solvent.
  • the reaction time between the compound ( ⁇ _1) and the compound ( ⁇ _2) is usually 0.1 to 10 hours, and preferably 0.2 to 3 hours.
  • the reaction temperature between the compound ( ⁇ _ 1) and the compound ( ⁇ _ 2) is usually 50 to 150 ° ⁇ , preferably 120 to 100 ° ⁇ .
  • the amount of the compound (I-2) to be used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, per 1 mol of the compound (I-1).
  • Examples of compound (I-1) include the compounds described below.
  • the compound (__2) a commercially available product may be used, and examples thereof include the compounds described below. ⁇ 02020/175394 109 ⁇ (: 17 2020/007180
  • the compound (I-1) is represented by, for example, a compound represented by the formula (I-3) (hereinafter sometimes referred to as a compound (_3)) and a formula (_4). It can be obtained by reacting with a compound (hereinafter, also referred to as compound (_ _4).).
  • a compound represented by the formula (I-3) hereinafter sometimes referred to as a compound (_3)
  • a formula (_4) It can be obtained by reacting with a compound (hereinafter, also referred to as compound (_ _4).).
  • Examples of the leaving group represented by Min 1 include a halogen atom, a toluenesulfonyl group, a trifluoromethylsulfonyl group, and the like.
  • the reaction between the compound (I _3) and the compound (I -4) is carried out by mixing the compound (I _3) and the compound (I _4).
  • the amount of compound ( ⁇ _4) used is usually ⁇ per 1 mol of compound ( ⁇ _3).
  • the amount is 1 to 5 mol, and preferably 0.5 to 2 mol.
  • the reaction between the compound ( ⁇ _3) and the compound ( ⁇ _4) may be carried out in the presence of a solvent.
  • Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methano ⁇ 0 2020/175 394 1 10 ⁇ (: 171? 2020 /007180
  • the reaction time between the compound (__) and the compound (I-4) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _ 3) and the compound (I-4) is usually 50 to 150 ° ⁇ .
  • Examples of the compound (I-3) include the compounds described below.
  • a commercially available product may be used as the compound (No. 14).
  • chlorocyan, bromocyan, paratoluenesulfonylcyanide, trifluoromethanesulphonylcyanide 1-chloromethyl-4-fluoro-1,4,diazonia biscyclo[2.2.2]octane bis(tetrafluoroborate (selectfluoro (8 _ 8 ⁇ 1 0116111 _108), benzoyl (phenyl iododonio) (trifluoromethanesulfonyl)methanide, 2,8-difluor-5-(trifluoromethyl)-1 5 1 to 1-dibenzo[ ⁇ , ] Thiofene-5-ium trifluoromethanesulfonate, 1 ⁇ 1 _ bromosuccinimide,
  • the compound (I _ 3) is a compound represented by the formula (I _ 5) (hereinafter, compound (I _ 3) ⁇ 02020/175394 111 ⁇ (: 171? 2020/007180
  • reaction between the compound (I_5) and the compound ( ⁇ _6) is carried out by mixing the compound (I_5) and the compound ( ⁇ _6).
  • the amount of the compound ( ⁇ _6) used is usually ⁇ per 1 mol of the compound ( ⁇ _5).
  • the amount is 1 to 5 mol, and preferably 0.5 to 2 mol.
  • the reaction between compound (__) and compound (__6) may be carried out in the presence of a solvent.
  • a solvent Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, evening butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, 1 ⁇ 1, 1 ⁇ 1_dimethyl acetamide, 1 ⁇ 1, 1 ⁇ 1-dimethylformamide, water, etc.
  • the reaction time between the compound ( ⁇ _5) and the compound ( ⁇ _6) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _5) and the compound ( ⁇ _6) is usually 50 to 150°°.
  • Examples of the compound include the compounds described below.
  • the compound (No. 6) includes ammonia; primary amines such as methylamine, ethylamine, ethanolamine, 4-hydroxybutylamine; dimethylamine, diethylamine, dibutylamine, pyrrolidine, piperidine, 3-hydroxylamine.
  • primary amines such as methylamine, ethylamine, ethanolamine, 4-hydroxybutylamine
  • secondary amines such as pyrrolidine, 4-hydroxypiperidine, and azetidine.
  • the compound ( ⁇ _ 1) is obtained by reacting the compound represented by the formula ( ⁇ _ 5 _ 1) (hereinafter, may be referred to as the compound ( ⁇ _5_ 1) .) You can get it anyway.
  • the amount of the compound (__6) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, per 1 mol of the compound (I_5_1).
  • the reaction between compound (__5_1) and compound (__6) may be carried out in the presence of a solvent.
  • a solvent Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, evening butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, 1 ⁇ 1, 1 ⁇ 1 _ Dimethylacetamide, 1 ⁇ 1, 1 ⁇ 1-dimethylformamide, water, etc.
  • the reaction time between the compound ( ⁇ _5_1) and the compound ( ⁇ _6) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _5_1) and the compound ( ⁇ _6) is usually 50 to 150 ° ⁇ .
  • Examples of the compound represented by the formula (I -5-1) include the compounds shown below. ⁇ 02020/175394 113 ⁇ (: 171? 2020 /007180
  • the compound ( ⁇ ) can also be obtained by reacting a compound represented by the formula ( ⁇ _7) (hereinafter sometimes referred to as compound (I-7).) with a compound ( ⁇ _6). ..
  • reaction between the compound ( ⁇ _7) and the compound ( ⁇ _6) can be carried out by mixing the compound ( ⁇ _7) and the compound (I_6) in the presence of a base and a methylating agent. Is preferred,
  • Examples of the base include the same bases used in the reaction between the compound ( ⁇ _1) and the compound ( ⁇ _2).
  • the amount of base used is usually 0.1 to 1 mol per 1 mol of the compound (_ _7). ⁇ 02020/175394 114 ⁇ (: 171? 2020 /007180
  • It is 5 mol, and preferably 0.5 to 2 mol.
  • methylating agent examples include the same methylating agents used for the reaction between the compound ( ⁇ _1) and the compound ( ⁇ _2).
  • the amount of the methylating agent used is usually 0.1 to 5 mol, and preferably 0.5 to 2 mol, per 1 mol of the compound (_7).
  • the amount of the compound (I-6) used is usually 0.1 to 10 mol, and preferably 0.5 to 5 mol, per 1 mol of the compound (I-7).
  • reaction of compound (I _7) with compound (I _6) may be carried out in the presence of a solvent.
  • the solvent include the same solvents as those used for the reaction between the compound ( ⁇ _1) and the compound ( ⁇ _2). Preferred are methanol, ethanol, isopropanol, toluene and acetonitrile.
  • reaction time between the compound ( ⁇ _7) and the compound (I-6) is usually from 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _7) and the compound (I -6) is usually 50 to 150°°.
  • Examples of the compound (No. 7) include the compounds described below.
  • Compound (I_7) can also be obtained by reacting the compound represented by formula (I-8) with compound (I-4). ⁇ 02020/175394 115 ⁇ (: 171? 2020/007180
  • reaction between the compound (I_8) and the compound (I-4) can be carried out by mixing the compound (I_8) and the compound ( ⁇ _4).
  • the reaction between the compound (__) and the compound (__4) is preferably performed in the presence of a base.
  • a base examples include the same bases used for the reaction between the compound ( ⁇ _ 1) and the compound ( ⁇ _2).
  • Preferred are metal hydroxides (more preferably alkali metal hydroxides), metal alkoxides (more preferably alkali metal alkoxides), amine compounds, and metal amide compounds (more preferably alkali metal amides).
  • the amount of the base used is usually 0.1 to 10 mol, preferably 0.5 to 2 mol, per 1 mol of the compound (_8).
  • the reaction of compound (__) with compound (__) may be performed in the presence of a solvent.
  • a solvent the same solvents as those used for the reaction between the compound ( ⁇ _1) and the compound ( ⁇ _2) can be mentioned.
  • Preferred are toluene, acetonitril, methanol, ethanol and isopropanol.
  • the reaction time between the compound ( ⁇ _8) and the compound (I -4) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound (_ _8) and the compound (I -4) is usually 50 to 150°°.
  • Examples of compound (I-8) include the compounds described below.
  • the compound (I _8) is obtained by reacting the compound (I _5) with the compound (I _2). ⁇ 02020/175394 116 ⁇ (: 171? 2020/007180
  • reaction between the compound ( ⁇ 15) and the compound ( ⁇ 1-2) can be carried out by mixing the compound ( ⁇ _5) and the compound ( ⁇ _2).
  • the reaction between the compound (__5) and the compound (__2) is preferably performed in the presence of a base.
  • the base include the same bases used for the reaction between the compound ( ⁇ _ 1) and the compound ( ⁇ _2).
  • the amount of the base used is usually from 0.1 to 5 mol, preferably from 0.5 to 2 mol, per 1 mol of the compound (5).
  • the reaction between the compound ( ⁇ _5) and the compound ( ⁇ _2) may be carried out in the presence of a solvent.
  • a solvent the same solvents as those used for the reaction between the compound ( ⁇ _1) and the compound ( ⁇ _2) can be mentioned.
  • Preferred are methanol, ethanol, isopropanol, toluene and acetonitrile.
  • the reaction time between the compound ( ⁇ _5) and the compound ( ⁇ _2) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _5) and the compound ( ⁇ _2) is usually 50 to 150°°.
  • the amount of the compound ( ⁇ _2) used is usually ⁇ per 1 mol of the compound ( ⁇ _5).
  • It is 1 to 10 mol, and preferably 0.5 to 2 mol.
  • compound (I-7) can also be obtained by reacting compound (I-5-1) with compound (I-2).
  • the reaction between the compound ( ⁇ _ 5 _ 1) and the compound ( ⁇ _ 2) is carried out by mixing the compound (I _ 5-1) and the compound ( ⁇ _2).
  • the amount of the compound ( ⁇ _2) used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, per 1 mol of the compound (I_5_1).
  • the reaction between the compound ( ⁇ _5_1) and the compound ( ⁇ _2) may be carried out in the presence of a solvent.
  • a solvent Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, evening butanol, 2-butanone, tet ⁇ 02020/175394 117 ⁇ (: 17 2020 /007180
  • Examples include lahydrofuran, diethyl ether, dimethyl sulfoxide, 1 ⁇ 1, 1 ⁇ 1_ dimethylacetamide, 1 ⁇ 1, 1 ⁇ 1-dimethylformamide, water and the like.
  • Preferred are benzene, toluene, ethanol and acetonitrile.
  • the reaction time between the compound ( ⁇ _5_1) and the compound ( ⁇ _2) is usually 0.1 to 10 hours.
  • the reaction temperature between the compound ( ⁇ _5_1) and the compound ( ⁇ _2) is usually 50 to 150°°.
  • the compound ( ⁇ ) can be obtained, for example, by reacting 2 molar equivalents of the compound ( ⁇ _7) with 1 molar equivalent of the compound represented by the formula (1 1 -1 ).
  • Examples of the compound represented by the formula (II_1) include the compounds described below.
  • the compound (IIII) can be obtained, for example, by reacting 2 molar equivalents of the compound (C-7) with 1 molar equivalent of the compound represented by the formula (IIII-1).
  • Examples of the compound represented by the formula ( ⁇ ⁇ ⁇ _ 1) include the compounds shown below. ⁇ 0 2020/175394 1 18 ⁇ (: 171? 2020 /007180
  • the compound ( ⁇ V) can be obtained, for example, by reacting 2 molar equivalents of the compound (I_7) with 1 molar equivalent of the compound represented by the formula (IV-1).
  • Examples of the compound represented by the formula ( ⁇ V-1) include the compounds described below.
  • Compound (V) can be obtained, for example, by reacting 2 molar equivalents of compound (I-1) with 1 molar equivalent of compound represented by formula (V-1). Ha, to # ⁇ # 4 (V ⁇ ))
  • Examples of the compound represented by the formula (V-...!) include the compounds described below.
  • the compound (V I) is, for example, the compound (I-1) 3 molar equivalent and the compound of the formula (V I -)
  • Examples of the compound represented by the formula (V I _ 1) include the compounds described below.
  • the compound (V I I) can be obtained, for example, by reacting 3 molar equivalents of the compound (I-7) with 1 molar equivalent of the compound represented by the formula (V I I-1).
  • Examples of the compound represented by the formula (V I 1 -1) include the compounds shown below.
  • the compound (V I I I) is, for example, the compound (I-7) 4 molar equivalent and the formula (V I I)
  • Examples of the compound represented by the formula (V ⁇ I -1) include the compounds shown below.
  • a polarizer is a film that has the function of extracting linearly polarized light from incident natural light.
  • the polarizer may be, for example, a stretched film having a dichroic dye adsorbed thereon, or a cured product of a composition containing a horizontally aligned polymerizable liquid crystal compound and a horizontally aligned dichroic dye. May be.
  • Examples of the stretched film having the dichroic dye adsorbed thereon include a polarizing film in which a dichroic dye such as iodine or a dichroic organic dye is adsorbed and oriented on a polyvinyl alcohol-based resin film.
  • the polyvinyl alcohol resin can be obtained by saponifying a polyvinyl acetate resin.
  • Examples of the polyvinyl acetate-based resin include polyvinyl acetate, which is a homopolymer of vinyl acetate, and a copolymer of vinyl acetate and a monomer copolymerizable with vinyl acetate.
  • Examples of monomers copolymerizable with vinyl acetate include unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and acrylic amides having an ammonium group.
  • the saponification degree of the polyvinyl alcohol-based resin is usually 85 mol% to 100 mol%, preferably 98 mol% or more.
  • the polyvinyl alcohol resin may be modified, for example, an aldehyde-modified polyvinyl former. ⁇ 0 2020/175394 121 ⁇ (: 171? 2020/007180
  • the degree of polymerization of the polyvinyl alcohol-based resin is usually 1,00 0 to 10 0,00 0, preferably 1,500 0 to 5,00 0.
  • a polyvinyl alcohol-based resin film is usually used as a raw film for a polarizer.
  • the polyvinyl alcohol resin can be formed into a film by a known method.
  • the thickness of the raw film is usually 1 to 150, and the film thickness is preferably 10 or more in consideration of ease of stretching.
  • a polarizer which is a stretched film having a dichroic dye adsorbed, is, for example, a step of uniaxially stretching a raw film, and dyeing the film with a dichroic dye The steps of adsorbing, treating the film with an aqueous solution of boric acid, and washing the film with water are performed, and finally dried to produce the film.
  • the thickness of the polarizer is usually 1 to 30.
  • a polarizer which is a stretched film having a dichroic dye adsorbed thereon is described in JP-A No. 10-1818 6133 and JP-A No. 20066-5009250. It can also be manufactured by a manufacturing method or the like.
  • the optical layer of the present invention is a stretched film having a dichroic dye adsorbed thereon, for example, a dichroic dye is dyed with a solution containing a compound (X) to obtain a dichroic dye. It can be obtained by adsorbing the dye and the compound (X) on the raw film.
  • the content of the compound (X) is not particularly limited, but from the viewpoint of the influence of the hue on the polarizer, it is usually 0.01 to 50 parts by mass relative to 100 parts by mass of the original resin film. , Preferably 0.1 to 10 parts by mass, more preferably 0.2 to 7 parts by mass, still more preferably 0.5 to 5 parts by mass.
  • the optical layer of the present invention is a polarizer which is a cured product of a composition containing a horizontally aligned polymerizable liquid crystal compound and a horizontally aligned dichroic dye, the polymerizable liquid crystal compound and the It is formed from a composition containing a colorant and a compound (X) (hereinafter sometimes referred to as composition).
  • the polymerizable liquid crystal compound may be a thermotropic liquid crystal compound. ⁇ 0 2020/175394 122 ⁇ (: 171? 2020 /007180
  • thermotropic liquid crystal compound showing a smectic liquid crystal phase is preferable.
  • the polymerizable liquid crystal compound is a liquid crystal compound having at least one polymerizable group.
  • the polymerizable group means a group that can participate in the polymerization reaction due to an active radical generated from a polymerization initiator or an acid, and examples thereof include a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, —Vinylphenyl group, acryloyloxy group, methacryloyloxy group, oxiranyl group, and xenotanyl group.
  • polymerizable liquid crystal compound examples include the polymerizable liquid crystal compounds described in JP-A No. 20 17 _ 107 2 3 2 and Japanese Patent No. 4 719 156.
  • the dichroic dye those having a maximum absorption wavelength in the range of 300 to 700 n are preferable.
  • examples thereof include an acridine dye, an oxazine dye, a cyanine dye, a naphthalene dye, an azo dye and an anthraquinone dye, and an azo dye is preferable.
  • dichroic dye examples include the dichroic dyes described in JP-A No. 2017-1710732.
  • the content of the polymerizable liquid crystal compound in the composition () is usually 70 to 99.9 mass% in the solid content of 100 mass% of the composition (), preferably 90 ⁇
  • the content of the compound (X) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 100 parts by mass of the polymerizable liquid crystal compound. Is 0.5 to 5 parts by mass.
  • the content of the dichroic dye is usually from 0.1 to 50 parts by mass, preferably from 0.1 to 20 parts by mass, and more preferably with respect to 100 parts by mass of the polymerizable liquid crystal compound. Is from 0.1 to 10 parts by mass.
  • the composition (8) may further contain a polymerization initiator, a leveling agent, a photosensitizer, a solvent and the like.
  • a polymerization initiator there is disclosed in JP-A-201-17-
  • a method for forming a polarizer from the composition (8) is to form a coating film of the composition (8). ⁇ 0 2020/175394 123 ⁇ (: 171? 2020/007180
  • the polymerizable liquid crystal compound After the temperature of the coating film is raised, the polymerizable liquid crystal compound is allowed to undergo a phase transition to a liquid crystal state (preferably a smectic liquid crystal state) to maintain the liquid crystal state (preferably the smectic liquid crystal state).
  • a liquid crystal state preferably a smectic liquid crystal state
  • Examples thereof include a method of polymerizing.
  • the coating film of the composition () can be formed, for example, by applying the composition () on a substrate.
  • the coating method include known methods such as spin coating method, per coating method and applicator method.
  • a dry coating film is formed by removing the solvent by drying or the like under the condition that the polymerizable liquid crystal compound does not polymerize. Further, in order to cause a phase transition of the polymerizable liquid crystal compound, the temperature of the polymerizable liquid crystal compound is raised to a temperature at which the phase transition of the polymerizable liquid crystal compound to a liquid phase or higher, and then the temperature is lowered to bring the polymerizable liquid crystal compound into a liquid crystal state (preferably a smectic liquid crystal state ) To the phase transition. Such phase transition may be performed after removing the solvent in the coating film, or may be performed simultaneously with the removal of the solvent.
  • a polarizer as a cured layer of the composition () is formed.
  • the polymerization method is preferably a photopolymerization method.
  • the thickness of the polarizer formed from the composition (8) is preferably 0.5 to 10 and more preferably 0.5 to 3.
  • the polarizer formed from the composition (8) is preferably formed on the alignment film.
  • the alignment film has an alignment regulating force for aligning the polymerizable liquid crystal compound in a desired direction.
  • Examples of the alignment film include an alignment film containing an alignment polymer, a photo-alignment film and a glob alignment film having a concavo-convex pattern and a plurality of grooves on the surface, and a stretched film stretched in the orientation direction. I like to have it.
  • alignment film examples include, for example, the alignment film described in Japanese Unexamined Patent Publication No. 20 17 _ 107 2 32 2.
  • the protective film is a film layer provided for the purpose of protecting other optical layers such as a polarizer.
  • a protective film made of a transparent resin film is used as the protective film.
  • the optical layer of the present invention is a protective film, it is formed from a composition containing a transparent resin film and the compound (X).
  • cellulose resin As transparent resin, cellulose resin, (meth)acrylic resin, polyester resin, polyolefin resin, polyamide resin, polyimide resin, polycarbonate resin, polyetheretherketone resin, polysulfone Examples include resin.
  • the cellulose-based resin is preferably a cellulose ester-based resin, that is, a resin in which at least a part of hydroxyl groups in cellulose is acetic acid esterified, a part of which is acetic acid esterified, and a part of which is other acid. It may be a mixed ester esterified with.
  • the cellulose ester-based resin is preferably an acetyl cellulose-based resin. Specific examples of the acetyl cellulose resin include triacetyl cellulose, diacetyl cellulose, cellulose acetate propionate, and cellulose acetate butyrate.
  • acetyl cellulose As the raw material cotton for acetyl cellulose, a cellulose raw material such as wood pulp and cotton linter, which are known in the Institute of Invention and Innovation published in 2000 0 1-1 745, can be used. Acetylcellulose can be synthesized by the method described in Wood Chemistry, pages 180-190 (Kyoritsu Shuppan, Ueda et al., 1964).
  • Examples of the (meth) acrylic resin include homopolymers of methacrylic acid alkyl ester or acrylic acid alkyl ester, and copolymers of methacrylic acid alkyl ester and acrylic acid alkyl ester.
  • Specific examples of the methacrylic acid alkyl ester include methyl methacrylate, ethyl methacrylate, and propyl methacrylate
  • specific examples of the acrylic acid alkyl ester include methyl acrylate, ethyl acrylate, and propyl methacrylate.
  • Examples include ropyl acrylate and the like.
  • a (meth)acrylic resin a commercially available general-purpose (meth)acrylic resin can be used.
  • As the (meth)acrylic resin a so-called impact-resistant (meth)acrylic resin may be used.
  • the (meth)acrylic resin examples include “Acrypet V 1 to 1” and “Acrypet Vitto” manufactured by Mitsubishi Rayon Co., Ltd. 1_208” and the like.
  • Polyester resin is a polymer resin having a repeating unit of ester bond in the main chain, and is generally obtained by condensation polymerization of polyvalent carboxylic acid or its derivative and polyvalent alcohol or its derivative.
  • Polyvalent carboxylic acids or their derivatives which give polyesters include terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, diphenyldicarboxylic acid, diphenylsulfonedicarboxylic acid, diphenoxyethanedicarboxylic acid, 5-sodium.
  • Aromatic dicarboxylic acids such as sulfone dicarboxylic acids, oxalic acid, succinic acid, adipic acid, sebacic acid, dimer acid, maleic acid, aliphatic dicarboxylic acids such as fumaric acid, 1,4-cyclohexanedicarbonic acid, etc.
  • Examples thereof include alicyclic dicarboxylic acids, oxycarboxylic acids such as paraoxybenzoic acid, and derivatives thereof.
  • Examples of the dicarboxylic acid derivative include dimethyl terephthalate, diethyl terephthalate, terephthalic acid 2-hydroxyethyl methyl ester, dimethyl 2,6-naphthalenedicarbonate, dimethyl isophthalate, dimethyl adipate, diethyl maleate, and the like.
  • Examples thereof include esterified products such as dimethyl dimer acid.
  • terephthalic acid isophthalic acid, 2,6-naphthalenedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and esterified products thereof are preferably used in terms of moldability and handleability.
  • Polyhydric alcohols or their derivatives that give polyesters include ethylene glycol, diethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5- Pentanediol, 1,6-hexanediol, neopentylgly ⁇ 0 2020/175 394 126 ⁇ (: 171? 2020 /007180
  • Aliphatic dihydroxy compounds such as kohl, polyethylene glycol, polyethylene glycol, polypropylene glycol, polyoxyalkylene glycols such as polytetramethylene glycol, alicyclic dihydroxy compounds such as 1,4-cyclohexanedimethanol and spiroglycol, bisphenol 8, aromatic dihydroxy compounds such as bisphenol 3, and derivatives thereof.
  • ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol and 1,4-cyclohexanedimethanol are preferably used in terms of moldability and handleability.
  • polyester-based resin examples include polyethylene terephthalate, polypropylene terephthalate, polyethylene naphthalate, polypropylene naphthalate, polytrimethylene terephthalate, polytrimethylene naphthalate, polycyclohexane dimethyl terephthalate, polycyclohexane dimethyl naphthalate and the like. .. Of these, polyethylene terephthalate or polyethylene naphthalate is preferable.
  • polystyrene-based resin examples include polyethylene-based resin, polypropylene-based resin, and cycloolefin-based resin, and the cycloolefin-based resin is preferable.
  • the cycloolefin-based resin is a thermoplastic resin having a unit of a monomer composed of cyclic olefin (cycloolefin) such as norbornene or polycyclic norbornene-based monomer, and is also called a thermoplastic cycloolefin-based resin.
  • the cycloolefin-based resin may be a hydrogenated product of the above-mentioned ring-opening polymer of cycloolefin or a ring-opening copolymer using two or more kinds of cycloolefins. It may be an addition polymer with an aromatic compound having a polymerizable double bond such as a group. A polar group may be introduced into the cycloolefin resin.
  • the unit of the cycloolefin monomer may be 50 mol% or less, but preferably about 15 to 50 mol%.
  • the unit of the cycloolefin monomer is the same as that described above. It can be a very small amount.
  • the unit of the chain olefin monomer is usually 5 to 80 mol%, and the unit of the vinyl compound-containing aromatic compound is usually 5 to 80 mol %. Is.
  • cycloolefin resin an appropriate commercially available product can be used.
  • Polyamide-based resin is a polymer resin containing an amid bond in its repeating unit as a main chain, such as an aromatic polyamide (aramid) or an aliphatic compound in which an aromatic ring skeleton is bound by an amid bond. Examples thereof include an aliphatic polyamide in which the skeleton is bound by an amide bond. Generally, it can be obtained by a polymerization reaction of a polyvalent carboxylic acid or its derivative and a polyvalent amine.
  • polycarboxylic acid or its derivative giving polyamide examples include terephthalic acid chloride, 2-chloro-terephthalic acid chloride, isophthalic acid dichloride, naphthalene dicarbonyl chloride, biphenyl dicarbonyl chloride, Examples include evening phenyldicarbonyl chloride.
  • polyamines examples include 4,4'-diaminodiphenyl ether, 3,4,-diaminodiphenyl ether, 4,4,dia ⁇ 0 2020/175394 128 ⁇ (: 171? 2020 /007180 Minodiphenyl sulfone, 3, 3'-Diaminodiphenyl sulfone, 2, 2
  • 2-bis[4-(4-aminophenyloxy)phenyl]propane, 2,2-bis(4-aminophenyl)hexafluoropropane and the like can be mentioned, but preferably 4,4′-diaminodiphenylsulfone, 3 ,3'-diaminodiphenyl sulfone, 2,2'-ditrifluoromethyl-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis(4-amino-3-methylphenyl)fluorene, Examples include 1,4-cyclohexanediamine and 1,4-norbornenediamine.
  • Polyimide-based resin is a polymer resin containing an imide bond in a repeating unit as a main chain, and is a condensation-type polyimide obtained by polycondensation using diamines and tetracarboxylic dianhydride as starting materials. Is common.
  • diamines aromatic diamines, alicyclic diamines, aliphatic diamines and the like can be used.
  • tetracarboxylic acid dianhydride aromatic tetracarboxylic acid dianhydride, alicyclic tetracarboxylic acid dianhydride, acyclic aliphatic tetracarboxylic acid dianhydride and the like can be used.
  • the diamines and the tetracarboxylic dianhydride may be used alone or in combination of two or more.
  • a tetracarboxylic acid compound selected from tetracarboxylic acid compound analogs such as acid chloride compounds may be used as a starting material.
  • the transparent resin is preferably any one of triacetyl cellulose resin, cycloolefin resin, (meth)acrylic resin, and polyester resin.
  • the storage modulus of the transparent resin at 23 ° ⁇ ' is usually 10 01 ⁇ 13 or more, preferably Or more, more preferably 500 IV! 3 or more ⁇ 0 2020/175394 129 ⁇ (: 171? 2020/007180
  • the content of the compound (X) is usually 0.001 to 100 parts by mass of the transparent resin.
  • a composition containing at least compound (X) and a transparent resin may be formed by any suitable shaping method.
  • compression molding method, transfer molding method, injection molding method, extrusion molding method, blow molding method, powder molding method, A molding method, a cast coating method (for example, a casting method), a calender molding method, a hot pressing method and the like can be mentioned.
  • the extrusion molding method or the cast coating method is preferable because the smoothness of the obtained optical layer can be increased and good optical uniformity can be obtained.
  • the molding conditions can be appropriately set depending on the composition and type of the resin used, desired characteristics, and the like.
  • the protective film further contains a plasticizer, an organic acid, a dye, an antistatic agent, a surfactant, a lubricant, a flame retardant, a filler, rubber particles, a phase difference adjusting agent, an ultraviolet absorber, a leveling agent, etc. You can leave.
  • a retardation film is an optical film exhibiting optical anisotropy, and a retardation film formed from a stretched film or a liquid crystal compound is applied to a base material to a position where optical anisotropy is exhibited by orientation.
  • a phase difference film is mentioned.
  • the stretched film examples include polyvinyl alcohol, poly carbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyether sulfone, polyvinylidene fluoride/polymethyl.
  • Examples include a stretched film obtained by stretching a polymer film made of methacrylate, acetyl cellulose, saponified ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. about 1.01 to 6 times.
  • acetyl cellulose ⁇ 0 2020/175394 130 ⁇ (: 171? 2020/007180
  • a polymer film obtained by uniaxially or biaxially stretching a polyester, a polycarbonate film or a cycloolefin resin film is preferable.
  • the optical layer of the present invention is a retardation film formed from a stretched film
  • it is formed from a resin composition containing the resin forming the polymer film and the compound (X).
  • a resin composition containing the resin forming the polymer film and the compound (X) For example, it can be produced by melt-extruding or casting a composition containing a resin having an arbitrary intrinsic birefringence value and at least the compound (X), and stretching the unstretched film.
  • the stretching may be uniaxial stretching or biaxial stretching.
  • stretching it is preferable to stretch at a temperature higher than the glass transition temperature of the resin. After stretching, it is preferable to perform a step of relaxing the residual stress of the film by heat.
  • the method described in Japanese Patent Laid-Open No. 2000-320550 can also be used.
  • the retardation film includes a zero retardation film, and is referred to as "_axial retardation film, low photoelasticity retardation film, wide viewing angle retardation film, etc.” Including film.
  • Zero lettering film means front lettering [3 ⁇ 4 6 and thickness direction lettering. And are both 15 to 15 n And is an optically isotropic film.
  • the zero retardation film include a film formed from a resin film made of a cellulose resin, a polyolefin resin (chain polyolefin resin, polycycloolefin resin, etc.) or a polyethylene terephthalate resin. Since it is easy to control the value, it is preferably formed of a cellulose resin or a polyolefin resin.
  • the zero retardation film can be produced by adjusting the stretching ratio by the same production method as that for the retardation film formed from the above-mentioned stretched film. It can also be prepared by stretching an unstretched film in which resins having unique birefringences of different positive and negative are combined.
  • the retardation film is preferably a retardation film in which optical anisotropy is exhibited by coating and orienting a liquid crystal compound. ⁇ 02020/175394 131 ⁇ (: 171? 2020/007180
  • a liquid crystal compound is applied.
  • a retardation film that exhibits optical anisotropy by orientation is obtained from a composition containing a liquid crystal compound and a compound (X) (hereinafter sometimes referred to as composition (Mitsumi)). It is formed.
  • the composition (Mitsumi) may further contain a photopolymerization initiator.
  • the content of the liquid crystal compound in the composition (Mi) is the solid content of the composition (Mi).
  • 100 mass % it is usually 50 to 99 mass %, preferably 75 to 90 mass %.
  • the content of the compound (X) is usually ⁇ . with respect to 100 parts by mass of the liquid crystal compound.
  • the amount is 01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass.
  • Examples of the film that exhibits optical anisotropy by coating/orientation of the liquid crystal compound include the following first to fifth forms.
  • First mode a retardation film in which a rod-shaped liquid crystal compound is aligned horizontally with respect to a supporting substrate.
  • Second mode a retardation film in which a rod-shaped liquid crystal compound is oriented in a direction perpendicular to a supporting substrate.
  • Phase difference film Fourth form Phase difference film in which a discotic liquid crystal compound is tilt-aligned
  • Biaxial retardation film in which a discotic liquid crystal compound is oriented in a direction perpendicular to a supporting substrate.
  • the first form, the second form, and the fifth form are preferably used.
  • these phase difference films may be laminated and used.
  • the retardation film is a layer made of a polymer in the alignment state of the polymerizable liquid crystal compound (hereinafter, also referred to as "optical anisotropic layer")
  • the retardation film has a reverse wavelength dispersion property. It is preferable to have The reverse wavelength dispersibility is an optical property in which the liquid crystal alignment in-plane retardation value at short wavelength is smaller than the liquid crystal alignment in-plane retardation value at long wavelength, and preferably the retardation film is That is, the expressions (7) and (8) are satisfied.
  • (S) represents the in-plane retardation value for light of wavelength S 01.
  • the retardation film when the retardation film is in the first form and has a reverse wavelength dispersibility, it is preferable because the coloring at the time of black display in the display device is reduced, and in the above formula (7), ⁇ . (550) £ ⁇ .93 is more preferred. further (550) £1 50 preferred
  • the front phase difference value 6 (550) may be adjusted to the range of ⁇ to 10 n, preferably the range of ⁇ to 5 n, and the phase difference value in the thickness direction is: Range from 10 to _30 ⁇ 1 ⁇ ⁇ !, preferably 1 Adjust to the range of.
  • the retardation value measured by inclining the retardation value in the thickness direction which means the refractive index anisotropy in the thickness direction, by 50° It can be calculated from That is, the phase difference value in the thickness direction [3 ⁇ 4 is the in-plane phase difference value [3 ⁇ 4 0 , measured with the fast axis tilted by 50 degrees with the tilt axis as the tilt axis. ⁇ 0 2020/175394 133 ⁇ (: 171? 2020/007180
  • the retardation film may be a multilayer film having two or more layers. Examples thereof include a retardation film having a protective film laminated on one side or both sides thereof, or a retardation film having two or more retardation films laminated via a pressure-sensitive adhesive or an adhesive.
  • the pressure-sensitive adhesive layer has adhesiveness (pressure-sensitive adhesiveness) and is used to bond optical layers to each other, to optical layers and other layers, or to bond other layers, or to fix optical layers to other objects.
  • adhesiveness pressure-sensitive adhesiveness
  • the pressure-sensitive adhesive layer may be, for example, a pressure-sensitive adhesive composition (hereinafter, referred to as pressure-sensitive adhesive composition (3)) containing a resin having a glass transition temperature of 30 ° or less, the compound (X), and a crosslinking agent.
  • pressure-sensitive adhesive composition (3) a pressure-sensitive adhesive composition containing a resin having a glass transition temperature of 30 ° or less, the compound (X), and a crosslinking agent.
  • Rubber-based resins, (meth)acrylic-based resins, silicone-based resins, etc. can be used as the resin having a glass transition temperature of 30 ° or less, but the viewpoints of transparency, durability, performance adjustment, etc. Therefore, the (meth)acrylic resin is preferable.
  • the (meth)acrylic resin in the pressure-sensitive adhesive composition is preferably a polymer containing a structural unit derived from a (meth)acrylic acid ester as a main component (preferably containing 50% by mass or more).
  • the position may include one or more structural units derived from a monomer other than the (meth)acrylic acid ester (for example, structural units derived from a monomer having a polar functional group).
  • Examples of the (meth)acrylic acid ester include a (meth)acrylic acid ester represented by the following formula (i).
  • Esters containing an aromatic ring skeleton of (meth)acrylic acid such as (meth)phenyl acrylate;
  • Substituent-containing (meth)acrylic acid alkyl ester in which a substituent is introduced into the alkyl group in the (meth)acrylic acid alkyl ester can also be mentioned.
  • Substituent-containing (meth) Substituent of acrylic acid alkyl ester is a group for substituting a hydrogen atom of an alkyl group, and specific examples thereof include a phenyl group, an alkoxy group, and a phenoxy group.
  • substituent-containing (meth)acrylate alkyl ester examples include (meth)acrylate 2-methoxyethyl, (meth)ethoxymethyl acrylate, (meth)phenoxyethyl acrylate, (meth)acrylic acid 2 —(2-Phenoxyethoxy)ethyl, (meth)acrylic acid phenoxydiethylene glycol, (meth)acrylic acid phenoxypoly(ethylene glycol) and the like.
  • the (meth)acrylic resin is a homopolymer having a glass transition temperature of less than 0 ° ⁇ , a structural unit derived from an alkyl acrylate (31), and a homopolymer of just 9 ° ⁇ . It is preferable to contain the structural unit derived from the above alkyl acrylate (32). Containing a structural unit derived from an alkyl acrylate (3 1) and a structural unit derived from an alkyl acrylate (3 2) is advantageous in increasing the high temperature durability of the pressure-sensitive adhesive layer. (Meta ⁇ 0 2020/175 394 136 ⁇ (: 171? 2020 /007180
  • acrylic acid alkyl ester (3 1) examples include ethyl acrylate, acrylic acid-and propyl, acrylic acid-and butyl, acrylic acid 11-pentyl, acrylic acid-and hexyl, Number of carbon atoms in the alkyl group such as 11-heptyl acrylate, acrylic acid-and octyl, 2-ethylhexyl acrylate, 1- and 4-nonyl acrylate, 1- and 4-decyl acrylate, _dodecyl acrylate 2 to 12 are included, and acrylic acid alkyl ester and the like are preferable, and preferred are butyl acrylate, octyl acrylate, and 2-ethylhexyl acrylate.
  • Two or more kinds of alkyl acrylates (31) may be used in combination.
  • alkyl acrylate 3 It is an alkyl acrylate other than 1).
  • alkyl ester acrylate (32) include methyl acrylate, cyclohexyl acrylate, isobornyl acrylate, stearyl acrylate, 1:-butyl acrylate, etc., methyl acrylate, cyclohexyl acrylate, acrylic It preferably contains isobornyl acid and the like, and more preferably contains methyl acrylate.
  • acrylic acid alkyl ester (32) 12 or more kinds may be used in combination.
  • the structural unit derived from the (meth)acrylic acid ester represented by the formula () is preferably 50% by mass or more in all structural units contained in the (meth)acrylic resin, It is preferably ⁇ 95% by mass, and more preferably 65 ⁇ 95% by mass or more.
  • a structural unit derived from a monomer other than the (meth)acrylic acid ester a structural unit derived from a monomer having a polar functional group is preferable, and a (meth)acrylic acid ester having a polar functional group is used.
  • the structural unit derived from is more preferable.
  • the polar functional group includes a hydroxy group, a carboxyl group, a substituted or unsubstituted amine group. ⁇ 0 2020/175 394 137 ⁇ (: 171? 2020 /007180
  • heterocyclic groups such as epoxy groups.
  • Monomers having a substituted or unsubstituted amino group such as acrylate and dimethylaminopropyl (meth)acrylate.
  • a monomer having a hydroxy group and/or a monomer having a carboxyl group is preferable from the viewpoint of the reactivity of the (meth)acrylic acid ester polymer with the crosslinking agent, and a monomer having a hydroxy group and a carboxyl group are preferable. It is more preferable to include any monomer having a group.
  • the monomer having a hydroxy group 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, and 6-hydroxyhexyl acrylate are preferable. Particularly, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate and 5-hydroxypentyl acrylate.
  • Acrylic acid is preferably used as the monomer having a carboxyl group.
  • the (meth)acrylic resin does not substantially contain a structural unit derived from a monomer having an amino group.
  • “not substantially containing” means that the amount is 0.1 part by mass or less in 100 parts by mass of all the structural units constituting the (meth)acrylic resin.
  • the content of the structural unit derived from the monomer having a polar functional group depends on the total structural unit of the (meth)acrylic resin 1 from the viewpoint of the durability of the adhesive (peeling or cohesive failure at high temperature).
  • 0 0 parts by weight preferably 20 parts by weight or less, more preferably 0.5 parts by weight or more and 15 parts by weight or less, further preferably 0.5 parts by weight or more and 10 parts by weight or less, particularly preferably It is 1 part by mass or more and 7 parts by mass or less.
  • the bleed resistance of the contained compound (X) it is preferably 0.5 part by mass or more, and more preferably 100 parts by mass with respect to the total structural units of the (meth)acrylic resin.
  • the amount is 1 part by mass or more, more preferably 5 parts by mass or more, and particularly preferably 7.5 parts by mass or more. In order to balance durability and bleed resistance, it is preferable to adjust the amount of polar functional groups according to the content of compound (X). ⁇ 0 2020/175394 140 ⁇ (: 171? 2020 /007180
  • the content of the structural unit derived from the monomer having an aromatic group is preferably 20 parts by mass or less, more preferably 4 parts by mass with respect to 100 parts by mass of all the structural units of the (meth)acrylic resin.
  • the amount is not less than 20 parts by mass and more preferably not less than 4 parts and not more than 16 parts by mass.
  • the (meth) structural unit derived from a monomer other than the acrylic acid ester includes a structural unit derived from a styrene-based monomer, a structural unit derived from a vinyl-based monomer, and a plurality of ( Examples also include structural units derived from a monomer having a (meth)acryloyl group, structural units derived from a (meth)acrylic amide-based monomer, and the like.
  • Styrene-based monomers include styrene; alkylstyrenes such as methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, and octylstyrene.
  • alkylstyrenes such as methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, and octylstyren
  • halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrostyrene; acetylstyrene; methoxystyrene; and divinylbenzene.
  • vinyl-based monomer vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl laurate, and other fatty acid vinyl esters; vinyl chloride, vinyl bromide, and other halogenated vinyls; Vinylidene halides such as vinylidene chloride; nitrogen-containing heteroaromatic vinyls such as vinylpyridine, vinylpyrrolidone, and vinylcarbazol; conjugated gens such as butadiene, isoprene, and chloroprene; Trill is mentioned.
  • Monomers having a plurality of (meth)acryloyl groups in the molecule include 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonane Diol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth ⁇ 0 2020/175394 141 ⁇ (: 171? 2020/007180
  • Monomers having two (meth)acryloyl groups in the molecule such as acrylate, tetraethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate; trimethylolpropane tri(meth)acrylate, etc. Examples thereof include a monomer having three (meth)acryloyl groups in the molecule.
  • Examples of (meth)acrylic amide-based monomer are 1 ⁇ 1-methylol (meth)acryl amide, 1 ⁇ 1— (2-hydroxyethyl) (meth)acrylic amide, 1 ⁇ 1— ( 3-hydroxypropyl) (meth) acrylic amide, 1 ⁇ 1— (4-hydroxybutyl) (meth) acrylic amide, 1 ⁇ 1 _ (5-hydroxypentyl) (medium) acrylic amide, 1 ⁇ 1 _ (6-hydroxyhexyl) (meth) acrylic amide, 1 ⁇ 1, 1 ⁇ 1 _ dimethyl (meth) acrylic amide, 1 ⁇ 1, 1 ⁇ 1 _ diethyl (meth) acrylic amide, 1 ⁇ 1— Isopropyl (meth) acrylic amide, 1 ⁇ 1— (3-dimethylaminopropyl) (meth) acrylic amide, 1 ⁇ 1 _ (1, 1 — dimethyl 3 -oxobutyl) (meth) acrylic amide, 1 ⁇ 1—[2—(2-ox) (
  • Weight average molecular weight of acrylic resin Is preferably from 500,000 to 250,000, more preferably from 600,000 to 180,000, further preferably from 700,000 to 170,000, particularly preferably from 10 to 100,000. It is between 0,000 and 160,000.
  • weight average molecular weight (! ⁇ /!) and number average molecular weight The molecular weight distribution (1 ⁇ /1/1 ⁇ / ⁇ ) expressed as a ratio with is usually 2 to 10 and preferably
  • the weight average molecular weight can be analyzed by gel permeation chromatography and is a value in terms of standard polystyrene.
  • the viscosity at 25 ° ⁇ is not more than 2 09 a 3 More preferably, it is 0.1 to 153.
  • the viscosity can be measured with a Brookfield viscometer.
  • the glass transition temperature (C9) of the (meth)acrylic resin is, for example, 60 to 20°°, preferably 50 to 15°°, more preferably 14.5 to 10°°, particularly It may be _ 40 to 0 °.
  • the glass transition temperature can be measured with a differential scanning calorimeter (mouth 30).
  • the (meth)acrylic resin can be produced by a known method such as a solution polymerization method, a bulk polymerization method, a suspension polymerization method and an emulsion polymerization method, and a solution polymerization method is particularly preferable.
  • the content of the (meth) acrylic resin in the adhesive composition (3) 100% by mass is usually 60% by mass to 99.9% by mass, preferably 70% by mass to 9 9
  • the content of the compound (X) is usually 0.001 to 50 parts by mass, preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the resin having a glass transition temperature of 30 ° or less. Parts, more preferably 0.2 to 10 parts by mass, particularly preferably ⁇ .
  • the crosslinking agent reacts with a polar functional group in the resin (for example, a hydroxy group, an amino group, a carboxyl group, a heterocyclic group, etc.).
  • the cross-linking agent forms a cross-linking structure with a resin or the like to form a cross-linking structure advantageous for durability.
  • cross-linking agent examples include an isocyanate cross-linking agent, an epoxy cross-linking agent, an aziridin cross-linking agent, a metal chelate cross-linking agent, and the like, and a pot life of the pressure-sensitive adhesive composition and an optical layer formed from the pressure-sensitive adhesive composition. From the viewpoints of durability, crosslinking speed, etc., an isocyanate-based crosslinking agent is preferable.
  • the isocyanate-based compound is preferably a compound having at least two isocyanato groups (1! ⁇ 1(30)) in the molecule, and examples thereof include aliphatic isocyanate-based compounds (eg hexamethylene diisocyanate), Alicyclic isocyanate compounds (eg isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate compounds (eg tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalene diisocyanate) , Triphenylmethane triisocyanate, etc.
  • aliphatic isocyanate-based compounds eg hexamethylene diisocyanate
  • Alicyclic isocyanate compounds eg isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xy
  • the cross-linking agent is an adduct of the above-mentioned isocyanate compound with a polyhydric alcohol compound (adduct) [eg, an additive with glycerol, trimethylolpropane, etc.], isocyanate It may be a derivative such as a urethane prepolymer-type isocyanate compound which is subjected to an addition reaction with a nurate, a biuret type compound, a polyether polyol, a polyester polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol and the like.
  • a polyhydric alcohol compound eg, an additive with glycerol, trimethylolpropane, etc.
  • isocyanate It may be a derivative such as a urethane prepolymer-type isocyanate compound which is subjected to an addition reaction with a nurate, a biuret type compound, a polyether polyol
  • the cross-linking agents may be used alone or in combination of two or more.
  • representative examples are aromatic isocyanate compounds (eg tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate compounds (eg hexamethylene diisocyanate). ⁇ 0 2020/175 394 144 ⁇ (: 171? 2020 /007180
  • Socyanate or an adduct of these polyhydric alcohol compounds (for example, glycerol, trimethylolpropane), or isocyanurate.
  • the cross-linking agent is an aromatic isocyanate compound and/or a polyhydric alcohol compound thereof, or an adduct of isocyanurate, it is advantageous for the formation of the optimum cross-linking density (or cross-linking structure).
  • the durability of the optical layer formed of the article (3) can be improved. In particular, when it is an adduct of a tolylene diisocyanate compound and/or a polyhydric alcohol compound of these, durability can be improved.
  • the content of the cross-linking agent is usually 0. 01 to 15 parts by mass with respect to 100 parts by mass of a resin having a glass transition temperature of 30 ° or lower (preferably (meal) acrylic resin). Parts, preferably 0.015 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass.
  • the pressure-sensitive adhesive composition (3) may further contain a silane compound.
  • silane compound examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethylsilane. Dimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethysilane. Examples include toxysilane, 3-mercaptopropyltrimethoxysilane and the like.
  • the silane compound may be a silicone oligomer. Specific examples of silicone oligomers are shown below in the form of a combination of monomers.
  • Cysilane oligomers 3-mercaptopropyltrietoxysilane-tetraethoxysilane oligomers and other mercaptopropyl group-containing oligomers; mercaptomethyltrimethoxysilane-tetramethoxysilane oligomers, mercaptomethyltrimethoxysilane-tetraetoxysilane oligomers , Mercaptomethyltriethoxysilane-tetramethoxysilane oligomers, mercaptomethyltriethoxysilane-tetraethoxysilane oligomers and other mercaptomethyl group-containing oligomers; 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycol Didoxypropyltrimethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane-te
  • Toxysilane oligomer 3-acryloyloxypropyl trimethyloxysilane-tetraetoxysilane oligomer, 3-acryloyloxypropyl triethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropyl triethoxysilane-tetraetoxysilane oligomer, 3 —Acryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-Tetraethoxysilane oligomer, 3-acryloyloxypropylmethylethyloxysilane-tetramethoxysilane oligomer, 3-acryloyloxy Acryloyloxypropyl group-containing oligomers such as propylmethylgetoxysilane-tetraethoxysilane oligomers; vinyltrimeth
  • the silane compound may be a silane compound represented by the following formula ( ⁇ ! 1) ⁇ 0 2020/175 394 147 ⁇ (: 17 2020/007180
  • M represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkanediyl group and the alicyclic hydrocarbon group.
  • M is an alkanediyl group having 1 to 20 carbon atoms such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a hexamethylene group, a heptamethylene group, and an octamethylene group; Butylene group (eg 1,2-cyclobutylene group), Cyclopentylene group (eg 1,2-cyclopentylene group), Cyclohexylene group (eg 1,2-Cyclohexylene group)
  • a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms such as a cyclooctylene group (for example, 1,2-cyclooctylene group), or an alkanediyl group and an alicyclic hydrocarbon group as described above. constituting the _ 0 1-1 2 - indicates a been substituted in one hundred and one or one 0_ ⁇ -. Preferred is an alkanediyl group having 1 to 10 carbon atoms.
  • ⁇ 7 is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Petit group,-butyl group, an alkyl group of carbon number 1-5 such as pentyl, 8, 9, 1 ⁇ , Examples of the alkyl group having 1 to 5 carbon atoms, or a carbon such as a methoxy group, an ethoxy group, a propoxy group, an I-propoxy group, a butoxy group, a butoxy group, and a 1-butoxy group. , [ ⁇ 1 and These silan compounds ( ⁇ 0 can be used alone or in combination of two or more. ⁇ 02020/175394 148 ⁇ (: 171? 2020 /007180
  • Examples of the silane compound represented by the formula (1) include (trimethoxysilyl)methane, 1,2-bis(trimethoxysilyl)ethane, 1,2-bis.
  • the content of the silane compound is usually 0.01 to 10 mass with respect to 100 parts by mass of a resin (preferably (meth)acrylic resin) having a glass transition temperature of 30 ° or less. Parts, preferably 0.03 to 5 parts by mass, more preferably 0.05 to 2 parts by mass, and still more preferably 0.1 to 1 parts by mass.
  • a resin preferably (meth)acrylic resin
  • the pressure-sensitive adhesive composition (3) may further contain an antistatic agent.
  • Examples of the antistatic agent include a surfactant, a siloxane compound, a conductive polymer and an ion compound, and an ionic compound is preferable.
  • Examples of the ionic compound include conventional ones.
  • Examples of the thione component constituting the ionic compound include organic cations and inorganic cations.
  • Examples of the organic cation include a pyridinium cation, a pyrrolidinium cation, a piperidinium cation, an imidazolium cation, an ammonium cation, a sulfonium cation and a phosphonium cation.
  • Examples of the inorganic cations include alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation, and alkaline earth metal cations such as magnesium cation and calcium cation.
  • alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation
  • alkaline earth metal cations such as magnesium cation and calcium cation.
  • pyridinium cation, imidazolium cation, pyrrolidinium cation, lithium cation, and potassium cation are preferable from the viewpoint of compatibility with the (meth)acrylic resin.
  • the anion component constituting the ionic compound may be either an inorganic anion or an organic anion, but an anion component containing a fluorine atom is preferable from the viewpoint of antistatic performance.
  • the anionic component containing a fluorine atom for example, hexafluoro phosphine benzoate anion (6 _), bis (trifluoromethanesulfonyl) imidate Doanion [( ⁇ 3 3_Rei 2) 2 1 ⁇ 1 -], bis (fluorosulfonyl) Imi Doanion [(3_Rei 2) 2 1 ⁇ 1 -]
  • Tetra(pentafluorophenyl)borate anion [( ⁇ 6 5 ) 4 Min -], and the like.
  • These ionic compounds can be used alone or in combination of two or more.
  • Tetra (pentafluorophenyl Enyl)borate anion [( ⁇ 6 ⁇ 0 2020/175394 150 ⁇ (: 171? 2020/007180
  • An ionic compound that is solid at room temperature is preferable from the viewpoint of the temporal stability of the antistatic performance of the optical layer formed from the pressure-sensitive adhesive composition (3).
  • the content of the antistatic agent is, for example, 0.001 to 20 parts by mass with respect to 100 parts by mass of a resin having a glass transition temperature of 30 ° C. or less (preferably (meth)acrylic resin). It is preferably 0.1 to 10 parts by mass, more preferably 1 to 7 parts by mass.
  • the pressure-sensitive adhesive composition (3) further contains one or two additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softening agent, a pigment, an anticorrosive agent, an inorganic filler, and light-scattering fine particles.
  • additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softening agent, a pigment, an anticorrosive agent, an inorganic filler, and light-scattering fine particles.
  • additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softening agent, a pigment, an anticorrosive agent, an inorganic filler, and light-scattering fine particles. The above can be contained.
  • the method for forming the pressure-sensitive adhesive layer from the pressure-sensitive adhesive composition (3) is to dissolve or disperse in a solvent to prepare a solvent-containing composition, which is then used as a base material (plastic film or the like) or A method of coating on the surface of another optical layer and drying may be mentioned.
  • the pressure-sensitive adhesive layer was formed by forming the pressure-sensitive adhesive layer on the release film, then adhering the pressure-sensitive adhesive layer to another layer, peeling the release film, and then the surface of the pressure-sensitive adhesive layer from which the release film was peeled off. It can also be attached to another layer.
  • the adhesive layer is formed on the release film, then attached to another release film and stored with the release film sandwiched between them, and the release film is peeled off before use. It may be attached to the optical layer.
  • the adhesive layer is used to bond the optical layers to each other, the optical layer to another layer, or the other layers to each other, or to fix the optical layer to another object.
  • the adhesive layer can be formed by curing the adhesive composition.
  • a thermosetting adhesive or active energy ray composition that heat-cures the thermosetting component to fix it is irradiated with active energy rays to cure.
  • An active energy ray curable adhesive or the like can be used.
  • the active energy ray-curable composition is a composition that is cured by being irradiated with an active energy ray.
  • Active energy rays include ultraviolet rays, electron rays, X-rays, ⁇ 0 2020/175394 151 ⁇ (: 171-1?2020/007180
  • Visible light may be used, and ultraviolet light is preferable.
  • an ultraviolet light source a light source having a light emission distribution with a wavelength of 400 n or less is preferable, and examples thereof include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a chemical lamp, a black light lamp, and a microwave-excited mercury lamp. , Metal halide lamps, etc.
  • the active energy ray-curable composition forming the optical layer of the present invention (hereinafter sometimes referred to as active energy ray-curable composition (2)) contains at least a photocurable component and a compound (X), Further, it is preferable to include a photoinitiator.
  • the photocurable component includes a compound or an oligomer (radical polymerizable compound) which is cured by a radical polymerization reaction upon irradiation with an active energy ray, and a compound (cation) which is cured by a cationic polymerization reaction upon irradiation with an active energy ray.
  • Polymerizable compound a compound that is cured by an anionic polymerization reaction, and the like.
  • a radically polymerizable compound, a cationically polymerizable compound, and an anionically polymerizable compound may be used in combination.
  • the radically polymerizable compound examples include radically polymerizable (meth)acrylic compounds.
  • the “(meth)acrylic compound” refers to a compound having one or more (meth)acryloyl groups in the molecule.
  • the active energy ray-curable adhesive composition can contain one or more radical-polymerizable (meth)acrylic compounds.
  • the (meth)acrylic compound includes a (meth)acrylate monomer having at least one (meth)acryloyloxy group in the molecule, a (meth)acrylamido monomer, and at least two (meth)acryloyl groups in the molecule.
  • examples thereof include (meth)acryloyl group-containing compounds such as (meth)acryl oligomers.
  • the (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule.
  • the (meth)acrylic compounds may be used alone or in combination of two or more. ⁇ 0 2020/175394 152 ⁇ (: 171? 2020/007180
  • the (meth)acrylate monomer includes a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule and a bifunctional (meth)acrylate having two (meth)acryloyloxy groups in the molecule. Examples thereof include (meth)acrylate monomers and polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule.
  • Examples of monofunctional (meth)acrylate monomers include methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isoptyl (meth)acrylate, Alkyl (meth)acrylates such as butyl (meth)acrylate and 2-ethylhexyl (meth)acrylate; aralkyl (meth)acrylates such as benzyl (meth)acrylate; terpene alcohol (meth), such as isobornyl (meth)acrylate Acrylate: Tetrahydrofurfuryl (meth) having a tetrahydrofurfuryl structure such as acrylate (meth) acrylate; Cyclohexyl (meth) acrylate, cyclohexylmethylmethacrylate, dicyclopentanyl acrylate, dicyclopentenyl (meth) acrylate Rate, 1,4-cyclohe
  • examples of the monofunctional (meth)acrylate monomer include a monofunctional (meth)acrylate having a hydroxyl group at an alkyl moiety; and a monofunctional (meth)acrylate having a carboxyl group at an alkyl moiety.
  • examples of monofunctional (meth)acrylates having a hydroxyl group at the alkyl moiety include 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2- Hydroxy 3-F ⁇ 0 2020/175 394 153 ⁇ (: 171? 2020 /007180
  • Examples include enoxypropyl (meth)acrylate, trimethylolpropane mono(meth)acrylate, and pentaerythritol mono(meth)acrylate.
  • the (meth)acrylic amide monomer includes 1 ⁇ !—methyl (meth)acrylic amide, 1 ⁇ 1—ethyl (meth)acrylic amide, 1 ⁇ 1—isopropyl (meth)acryl amide, (Meth)acrylic amide, 1 ⁇ 1 _-butyl (meth)acrylic amide, 1 ⁇ 1—hexyl (meth)acrylic amide etc.
  • Hydroxyalkyl (meth) acrylate 1 ⁇ 1—acryloylpyrrolidine, 3-acryloyl-2-oxazolidinone, 4-acryloylmorpholine, 1 ⁇ 1 _acryloylbiperidine, -methacryloylbiperidine and the like.
  • Tetrafluoroethylene glycol di(meth)acrylate and other halogen-substituted alkylene glycol di(meth)acrylates
  • Di(meth)acrylate of aliphatic polyol such as trimethylolpropane di(meth)acrylate, ditrimethylolpropane di(meth)acrylate, pentaerythritol di(meth)acrylate;
  • Hydrogenated dicyclopentadienyl di(meth)acrylate hydrogenated dicyclopentadiene such as tricyclodecane dimethanol di(meth)acrylate, or di(meth)acrylate of tricyclodecane dialkanol;
  • Di(meth)acrylate of dioxane glycol or dioxane dialkanol such as 1,3-dioxane-2,5-diyldi(meth)acrylate [alias: dioxane glycol di(meth)acrylate];
  • Bisphenol octaethylene oxide adduct diacrylates bisphenol _ethylene oxide adducts diacrylates, etc. bisphenol octanol or di(meth) acrylate adducts of bisphenol alkylene oxide adducts;
  • Bisphenol octadiglycidyl ether acrylic acid adduct bisphenol diglycidyl ether acrylic acid adduct, etc.
  • Trifunctional or higher polyfunctional (meth)acrylate monomers include glycerin tri(meth)acrylate, alkoxylated glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate.
  • Ditrimethylolpropane tetra(meth)acrylate pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)
  • Examples of the (meth) acrylic oligomer include urethane (meth) acrylic oligomer, polyester (meth) acrylic oligomer, and epoxy (meth) acrylic oligomer.
  • Urethane (meth) acrylic oligomer is a urethane bond (one
  • the hydroxyl group-containing (meth)acrylic monomer used in the urethanization reaction can be, for example, a hydroxyl group-containing (meth)acrylate monomer, and specific examples thereof include 2-hydroxyethyl (meth)acrylate and 2-hydroxyl.
  • hydroxyl group-containing (meth) acrylate monomers include 1 ⁇ 1-hydroxyethyl (meth) acrylic amide, 1 ⁇ 1-hydroxyalkyl (meth) acrylic such as 1 ⁇ 1-methylol (meth) acrylic amide. Contains amide monomer.
  • Examples of the polyisocyanate to be subjected to the urethane-forming reaction with a hydroxyl group-containing (meth)acrylic monomer include hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate and these Diisocyanates obtained by hydrogenating aromatic isocyanates (eg hydrogenated tolylene diisocyanate, hydrogenated xylylene diisocyanate, etc.), triphenylmethane triisocyanate, dibenzylbenzene triisocyanate, etc. Examples include tree isocyanate and polyisocyanate obtained by multiplying the above diisocyanate.
  • polyester polyols and polyetherpolyols can be used as the polyol used for forming the urethane compound containing a terminal isocyanato group by the reaction with a polyisocyanate.
  • polyester polyols and polyetherpolyols can be used as the polyol used for forming the urethane compound containing a terminal isocyanato group by the reaction with a polyisocyanate.
  • Aliphatic and alicyclic polyols include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane and ditriol.
  • examples thereof include methylolpropane, pentaerythritol, dipentaerythritol, dimethylolheptane, dimethylolpropionic acid, dimethylolbutanoic acid, glycerin and hydrogenated bisphenol-8.
  • the polyester polyol is obtained by a dehydration condensation reaction between the above-mentioned polyol and a polybasic carboxylic acid or its anhydride.
  • polybasic carboxylic acids or anhydrides thereof are represented by adding “(anhydrous)” to what may be an anhydride: (anhydrous) succinic acid, adipic acid, (anhydrous) maleic acid, (anhydrous) ) Itaconic acid, (anhydrous) trimellitic acid, (anhydrous) pyromellitic acid, (anhydrous) phthalic acid, isophthalic acid, terephthalic acid, and hexahydro (anhydrous) phthalic acid.
  • the polyether polyol may be, in addition to polyalkylene glycol, polyoxyalkylene-modified polyol obtained by the reaction of the above-mentioned polyol or dihydroxybenzenes and alkylene oxide.
  • the polyester (meth)acrylate oligomer means an oligomer having an ester bond and at least two (meth)acryloyloxy groups in the molecule.
  • the polyester (meth)acrylate oligomer can be obtained by subjecting (meth)acrylic acid, polybasic carboxylic acid or its anhydride, and polyol to dehydration condensation reaction.
  • polybasic carboxylic acid or its anhydride examples include succinic anhydride, adipic acid, maleic anhydride, itaconic anhydride, trimellitic anhydride, pyromellitic dianhydride, hexahydrophthalic anhydride, phthalic acid, succinic acid, and maleic acid. , Itaconic acid, trimellitic acid, pyromellitic acid, hexahydrophthalic acid, phthalic acid, isophthalic acid, terephthalic acid and the like. ⁇ 0 2020/175394 158 ⁇ (: 171? 2020 /007180
  • polystyrene resin examples include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol. And dipentaerythritol, dimethylolheptane, dimethylolpropionic acid, dimethylolbutanoic acid, glycerin, hydrogenated bisphenol-8 and the like.
  • the epoxy (meth) acrylic oligomer can be obtained by an addition reaction between polyglycidyl ether and (meth)acrylic acid.
  • the epoxy (meth)acryl oligomer has at least two (meth)acryloyloxy groups in the molecule.
  • polyglycidyl ether examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, and bisphenol octadiglycidyl ether.
  • the cationically polymerizable compound is a compound or an oligomer which undergoes a cationic polymerization reaction upon irradiation with active energy rays such as ultraviolet rays, visible rays, electron beams, and X-rays and heating to cure.
  • active energy rays such as ultraviolet rays, visible rays, electron beams, and X-rays and heating to cure.
  • examples of the cationically polymerizable compound include epoxy compounds, oxetane compounds, vinyl compounds and the like.
  • the cationically polymerizable compound may be used alone or in combination of two or more kinds.
  • the cationically polymerizable compound is preferably an epoxy compound.
  • the epoxide compound is a compound having one or more (preferably two or more) epoxy groups in the molecule.
  • Examples of the epoxy compound include an alicyclic epoxy compound, an aromatic epoxy compound, a hydrogenated epoxy compound, and an aliphatic epoxy compound.
  • the alicyclic epoxy compound is a compound having one or more epoxy groups bonded to the alicyclic ring in the molecule.
  • the epoxy group bonded to the alicyclic ring is, for example, ⁇ 02020/175394 159 ⁇ (: 171? 2020/007180
  • Examples thereof include an epoxycyclopentane structure and an epoxycyclohexane structure.
  • Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate; 3,4-epoxy _ 6-methylcyclohexylmethyl 3,4-epoxy _ 6-methylcyclohexane Carboxylate; Ethylene bis(3,4-epoxycyclohexancarboxylate); Bis(3,4-epoxycyclohexylmethyl) adipate; Bis(3,4-epoxy _ 6-methylcyclohexylmethyl) adipate Polyethylene glycene bis (3,4-epoxycyclohexylmethylether) Ethyleneglycol bis (3,4-epoxycyclohexylmethylether); 2, 3, 1 4, 1 5 -jepoxy _7 , 1 1, 1 8, 2 1-Tetraoxatrispyro [5.2.2.5
  • the aromatic epoxy compound is a compound having an aromatic ring and an epoxy group in the molecule.
  • aromatic epoxy compounds include bisphenol octadiglycyl ether, bisphenol diglycidyl ether, bisphenol 3 diglycidyl ether, and other bisphenol type epoxy compounds or their oligomers; phenol novolac epoxy resin, cresol novolak epoxy resin.
  • Novolak type epoxy resins such as hydroxybenzaldehyde phenol novolac epoxy resin; 2, 2, 4, 4, 4-Tetrahydroxydiphenylmethane glycidyl ether, 2, 2, 4,4, 4-Tetrahydroxybenzophenone glycidyl
  • Polyfunctional epoxy compounds such as ether; polyfunctional epoxy resins such as epoxylated polyvinylphenol
  • the hydrogenated epoxy compound is a glycidyl ether of a polyol having an alicyclic ring, and an aromatic polyol is selectively converted into an aromatic ring under pressure in the presence of a catalyst. ⁇ 0 2020/175 394 160 ⁇ (: 171? 2020/007180
  • the nuclear-hydrogenated polyhydroxy compound obtained by carrying out the hydrogenation reaction may be glycidyl etherified.
  • aromatic polyols include, for example, bisphenol type compounds such as bisphenol-8, bisphenol and bisphenol3; phenol novolac resin, cresol novolac resin, novolak type resin such as hydroxybenzaldehyde phenol novolac resin; tetrahydroxydif Includes polyfunctional compounds such as phenylmethane, tetrahydroxybenzophenone, and polyvinylphenol.
  • a glycidyl ether can be obtained by reacting epichlorohydrin with an alicyclic polyol obtained by subjecting an aromatic ring of an aromatic polyol to a hydrogenation reaction.
  • the hydrogenated epoxy compounds a diglycidyl ether of hydrogenated bisphenol 8 is preferable.
  • the aliphatic epoxy compound is a compound having at least one oxirane ring (3-membered cyclic ether) bonded to an aliphatic carbon atom in the molecule.
  • monofunctional epoxy compounds such as butyl glycidyl ether and 2-ethylhexyl glycidyl ether; bifunctional epoxide compounds such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether and neopentyl glycol diglycidyl ether Epoxy compounds; Trifunctional or higher functional epoxy compounds such as trimethylolpropane triglycidyl ether and pentaerythritol tetraglycidyl ether; Epoxy groups directly bonded to alicyclic rings such as 4-vinylcyclohexene dioxide and limonene dioxide 1 And an epoxy compound having an oxirane ring bonded to an alicyclic rings such
  • the oxetane compound is a compound containing at least one oxetane ring (oxetanyl group) in the molecule.
  • examples of the oxetane compound include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, 1,4-bis[ ⁇ (3-ethyloxetane-3-yl)methokidi ⁇ methyl]benzene,
  • Examples of the vinyl compound include aliphatic or alicyclic vinyl ether compounds.
  • Examples of the vinyl compound include s-amyl vinyl ether, s-amyl vinyl ether, n _hexyl vinyl ether, n _octyl vinyl ether, 2-ethylhexyl vinyl ether, closed decyl vinyl ether, stearyl vinyl ether, oleyl vinyl ether, etc.
  • Vinyl ethers of alkyl or alkenyl alcohols such as 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether; cyclohexyl vinyl ether, 2-methylcyclohexyl vinyl ether, cyclohexyl methyl vinyl ether, benzyl vinyl ether, etc.
  • Vinyl ethers of monoalcohols having aliphatic or aromatic rings having aliphatic or aromatic rings; glycerol monovinyl ether, 1,4-butanediol monovinyl ether, 1,4-butanediol divinyl ether, 1,6-hexanediol divinyl ether, neopentyl glycol diether Vinyl ether, pentaerythritol divinyl ether, pentaerythritol tetravinyl ether, trimethylolpropane divinyl ether, trimethylolpropane trivinyl ether, 1,4-dihydroxycyclohexane monovinyl ether, 1,4-dihydroxycyclohexanedivinyl ether, Mono-polyvinyl ethers of polyhydric alcohols such as 1,4-dihydroxymethylcyclohexane monovinyl ether and 1,4-dihydroxymethylcyclohexane
  • the content of the photocurable component is the solid content of the active energy ray-curable composition (2).
  • the content of the compound (X) is usually ⁇ . with respect to 100 parts by mass of the photocurable component.
  • the photopolymerization initiator contains a photoradical polymerization initiator. Further, it may further contain a thermal radical polymerization initiator.
  • the photoradical polymerization initiator is one which initiates the polymerization reaction of the radical-curable compound upon irradiation with an active energy ray such as visible light, ultraviolet ray, X-ray, or electron beam.
  • Photo-radical polymerization initiators include acetophenone, 3-methylacetophenone, benzyl dimethyl ketal, 1-(4-isopropylphenyl) _ 2-hydroxy _ 2 -methyl propane _ 1 -one, 2-methyl-
  • Acetophenone-based initiators such as 2-hydroxy _ 2-methyl-1-phenyl propane _ 1-one; benzophenone, 4-chlorobenzophenone, 4, 4,
  • Benzophenone-based initiators such as diaminobenzophenone; Benzoinether-based initiators such as benzoinpropyl ether, benzoimme, chill ether benzoin ethyl ether; Thioxanthone-based initiators such as 4-isopropylthioxanthone; xanthone, fluorenone, camphorquinone, benzua Ludehide, anthraquinone, etc.; 1-[4-(phenylthio) phenyl] -,
  • Examples include oxime ester-based initiators such as -, 1-( ⁇ -acetyloxime)-ethanone.
  • Two or more photo-radical polymerization initiators may be used in combination. ⁇ 0 2020/175 394 163 ⁇ (: 171? 2020/007180
  • the content of the photoradical polymerization initiator is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the radically polymerizable compound, and It is preferably 0.5 to 5 parts by mass.
  • the radical polymerizable compound can be sufficiently hardened.
  • the photopolymerization initiator is a photocation polymerization initiator.
  • the photocationic polymerization initiator is a compound which, when irradiated with an active energy ray such as visible light, ultraviolet ray, X-ray, or electron beam, generates a cationic species or vasic acid to start the polymerization reaction of the cationically curable compound. is there .
  • Examples of the compound that produces a cation species or a Lewis acid upon irradiation with active energy rays include onium salts such as aromatic iodonium salts and aromatic sulfonium salts; aromatic diazonium salts; iron-arene complexes and the like.
  • the aromatic iodonium salt is a compound having a diaryliodonium cation, and typical examples of the cation include diphenyliodonium cation.
  • the aromatic sulfonium salt is a compound having a triarylsulfonium cation, and typical examples of the cation include a triphenylsulfonium cation and 4,4′-bis(diphenylsulfonio)diphenylsulfide cation. ..
  • the aromatic diazonium salt is a compound having a diazonium cation, and typical examples of the cation include a benzenediazonium cation.
  • the iron-arene complex is typically cyclopentagenyl iron ( ⁇ ) arene cation complex salt.
  • the cation shown above is paired with an anion (anion) to form a photocation polymerization initiator.
  • An example of the anion that constitutes the photocationic polymerization initiator is a special phosphorus-based anion [(8) _, Hexafluorophosphate Toanion 6 -, hexafluoroantimonate anion 3 spoon 6 -, penta-fluoro-hydroxy antimonate anion 3 spoon 5 ( ⁇ !) -, Hekisafuruo ⁇ 0 2020/175 394 164 ⁇ (: 171? 2020 /007180
  • the cationic photopolymerization initiator may be used in combination of two or more kinds.
  • the aromatic sulphonium salt has an ultraviolet absorbing property even in the wavelength region around 300 n, and therefore it is excellent in curability and can give a cured product having good mechanical strength and adhesive strength. Therefore, it is preferable.
  • the content of the photo-cationic polymerization initiator is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, relative to 100 parts by mass of the cationically polymerizable compound. And more preferably 0.5 to 5 parts by mass.
  • the cationically polymerizable compound can be sufficiently cured.
  • the adhesive composition preferably contains a radical-polymerizable curable component, and a radical-polymerizable (meth)acrylic component is included. It is preferable to include. From the viewpoint of curability, it is preferable to include an oxime ester-based photoradical polymerization initiator. Further, it is preferably a non-solvent system.
  • thermosetting adhesive a thermosetting compound having a functional group capable of reacting with heat
  • the thermosetting compound may be a monomer, an oligomer or a polymer.
  • Functional groups that can react by heat include epoxy groups, hydroxy groups, carboxyl groups, amino groups, thiol groups, isocyanate groups, silanol groups, alkoxysilyl groups, cyanate groups, amid groups, acid anhydride groups, aldehyde groups. , Acetoacetyl group, diketone group and the like.
  • Thermosetting components may use only a single functional group species, but at lower temperatures ⁇ 0 2020/175 394 165 ⁇ (: 171? 2020 /007180
  • a crosslinking agent may be used in combination.
  • the adhesive composition can contain additives as necessary.
  • Additives include ion trap agents, chain transfer agents, polymerization accelerators, sensitizers, sensitization aids, fillers, flow control agents, plasticizers, defoamers, leveling agents, translucent fine particles, Solvents such as organic solvents, thermal polymerization initiators, blocking agents, antifouling agents, surfactants, curing agents, viscosity adjusting agents, antifouling agents, slip agents, refractive index adjusting agents, dispersants and the like.
  • the hard coat layer has a function of preventing scratches and dents in the optical layer and other layers, and is often laminated on a protective film or the like.
  • the hard coat layer can be formed from the same components as the adhesive composition described above.
  • the composition forming the hard coat layer is preferably an active energy ray-curable composition (2).
  • the hard coat layer contains a photo-radical-polymerizable component, more preferably a (meth)acryl-based component. Further, since it is easy to sufficiently enhance scratch resistance and hardness, it is preferable to contain a polyfunctional (meth)acrylate having 3 or more functional groups. Further, it is preferable to include a urethane acrylic oligomer for imparting flexibility. Further, it preferably contains a photo radical initiator. From the viewpoint of curability, the photo radical initiator is preferably an oxime ester-based initiator. Furthermore, from the viewpoint of the leveling property of the liquid surface at the time of coating the base material, it is preferable to include a leveling agent.
  • leveling agent examples include known ones such as a fluorine leveling agent, a silicone leveling agent, and an acrylic leveling agent.
  • the leveling agent is contained, it is preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the photocurable component.
  • the composition forming the hard coat layer may be an organic solvent, water, or no solvent. Viscosity is easy to control and it can be dissolved and cured ⁇ 0 2020/175 394 166 ⁇ (: 171? 2020/007180
  • an organic solvent From the viewpoint of abundant types of components and the leveling property, it is preferable to include an organic solvent.
  • Organic solvents include aliphatic hydrocarbons such as hexane, cyclohexane and octane; aromatic hydrocarbons such as toluene and xylene; methanol, ethanol, 1-propanol, isopropanol, 11_butanol, 3_butanol, 1 _ Butanol, benzyl alcohol, ethylene glycol, cyclohexanol, and other alcohols; methyl ethyl ketone, methyl isoptylketone, cyclopentanone, cyclohexanone, heptanone, diisoptyl ketone, diethyl ketone, and other ketones; ethyl acetate, acetic acid Esters such as butyl and isopropyl acetate; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, propylene
  • the active energy ray-curable composition (2) contains an organic solvent, it is necessary to evaporate the organic solvent after coating. Therefore, it is desirable that the organic solvent has a boiling point in the range of 60 ° to 160 ° . Also, at that 20 ° ⁇ ⁇ 0 2020/175 394 167 ⁇ (: 171? 2020/007180
  • the saturated vapor pressure is preferably in the range of 0.11 ⁇ 3 to 201 ⁇ 3.
  • the active energy ray-curable composition (2) is applied onto a substrate (plastic film or the like) or another optical layer to form a coating film, which is dried if necessary, and then the above coating film is applied.
  • the optical layer of the present invention can be formed. That is, the cured product of the active energy ray-curable composition (2) is the optical layer of the present invention.
  • the method for forming a coating film by applying the active energy ray-curable composition (2) include spin coating method, dipping method, spraying method, die coating method, bar coating method, mouth coater method, and meniscus coater method. Examples include various known methods such as a flexographic printing method, a screen printing method, and a bead coater method.
  • the drying method is not particularly limited.
  • the drying temperature is usually 30 to 120 ° , and the drying time is preferably 3 to 300 seconds.
  • the coating film can be cured by coating the coating film with the active energy ray-curable composition (2) and then irradiating the coating film with the active energy ray.
  • the active energy ray irradiation intensity is determined by the composition of the active energy ray-curable composition (2), and the light irradiation intensity in the wavelength range effective for activating the photopolymerization initiator is ⁇ .
  • the light irradiation time of the active energy ray-curable composition (2) to the coating film is determined by the composition of the active energy ray-curable composition (2).
  • the integrated light quantity represented as the product is
  • the thickness of the hard coat layer is preferably 0.5 to 20 and more preferably 1 to 20. 10 is more preferable, 2 to 7 is more preferable, and 3 to 5 is particularly preferable.
  • the content of the compound (X) is usually ⁇ with respect to 100 parts by mass of the photocurable component. .1 to 50 parts by mass, preferably 0.1 to 20 parts ⁇ 0 2020/175 394 168 ⁇ (: 171? 2020 /007180
  • Parts by weight more preferably 0.5 to 10 parts by mass, and even more preferably 0.5 to 5 parts by mass.
  • the present invention also includes an optical laminate including the optical layer of the present invention and another layer.
  • the other layer may be any of the optical layers described above.
  • the optical layer containing the compound (X) may be any one layer or plural layers.

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