WO2018101122A1 - Composition polymérisable et corps optiquement anisotrope dans lequel celui-ci est utilisé - Google Patents

Composition polymérisable et corps optiquement anisotrope dans lequel celui-ci est utilisé Download PDF

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WO2018101122A1
WO2018101122A1 PCT/JP2017/041786 JP2017041786W WO2018101122A1 WO 2018101122 A1 WO2018101122 A1 WO 2018101122A1 JP 2017041786 W JP2017041786 W JP 2017041786W WO 2018101122 A1 WO2018101122 A1 WO 2018101122A1
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polymerizable
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formula
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PCT/JP2017/041786
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浩一 延藤
桑名　康弘
美花 山本
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Dic株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • 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
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation

Definitions

  • the present invention relates to a polymer having optical anisotropy that requires various optical properties, a polymerizable composition useful as a component of a film, an optical anisotropic body comprising the polymerizable composition, a retardation film, and optical compensation.
  • a compound having a polymerizable group is used in various optical materials.
  • a polymer having a uniform orientation by aligning a polymerizable composition containing a polymerizable compound in a liquid crystal state and then polymerizing it.
  • Such a polymer can be used for polarizing plates, retardation plates and the like necessary for displays.
  • two or more types of polymerization are used to satisfy the required optical properties, polymerization rate, solubility, melting point, glass transition temperature, polymer transparency, mechanical strength, surface hardness, heat resistance and light resistance.
  • a polymerizable composition containing a functional compound is used. In that case, the polymerizable compound to be used is required to bring good physical properties to the polymerizable composition without adversely affecting other properties.
  • Patent Documents 1 to 3 When using a polymerizable compound inferior in solubility, it is very difficult to suppress coating unevenness because there are limitations on the types of solvents that can be used.
  • a film with unevenness is used for, for example, a display, the brightness of the screen is uneven or the color is unnatural, which causes a problem of greatly reducing the quality of the display product. Therefore, there has been a demand for the development of a polymerizable liquid crystal compound having reverse wavelength dispersibility or low wavelength dispersibility excellent in solubility that can solve such problems.
  • the problem to be solved by the present invention is to provide a polymerizable composition having reverse wavelength dispersibility or low wavelength dispersibility which is difficult to precipitate at room temperature after solvent drying and has good orientation, and polymerizes the composition.
  • Another object of the present invention is to provide a polymerizable composition in which haze does not easily occur when a film-like polymer obtained in this way is produced.
  • an optical anisotropic body, retardation film, optical compensation film, antireflection film, lens, lens sheet, liquid crystal display device, organic light emitting display device, and lighting device using the polymerizable composition, comprising the polymerizable composition It is to provide optical parts, colorants, security markings, laser emission members, polarizing films, coloring materials, printed materials, and the like.
  • the present invention has been intensively studied with a focus on a polymerizable composition using a specific polymerizable compound having one or more polymerizable groups and a specific non-liquid crystalline monomer.
  • the present invention has been provided. That is, the present invention a) a polymerizable liquid crystal compound having one or more polymerizable groups and satisfying formula (I), Re (450 nm) / Re (550 nm) ⁇ 1.0 (I) (In the formula, Re (450 nm) is when the polymerizable liquid crystal compound having one or more polymerizable groups is aligned on the substrate so that the major axis direction of the molecule is substantially horizontal to the substrate.
  • the in-plane retardation at a wavelength of 450 nm, Re (550 nm), indicates that the major axis direction of the molecule is substantially the same as that of the substrate on the substrate with the polymerizable liquid crystal compound having one or more polymerizable groups.
  • Re 550 nm
  • a polymerizable composition containing at least one non-liquid crystalline polymerizable compound having a molecular weight of 150 to 600 is provided.
  • an optical anisotropic body, a retardation film, an optical compensation film, an antireflection film, a lens, a lens sheet, a liquid crystal display device using the polymerizable composition, and an organic light emitting display device comprising the polymerizable composition Provide lighting elements, optical components, colorants, security markings, laser emission members, printed materials, and the like.
  • the polymerizable composition of the present invention precipitates at room temperature by simultaneously using a specific polymerizable liquid crystal compound having one or more polymerizable groups and at least one non-liquid crystalline polymerizable compound. It is difficult to obtain a polymerizable composition excellent in orientation, and a polymer, an optical anisotropic body, a retardation film, etc. excellent in productivity with a low haze of the coating film can be obtained.
  • liquid crystal compound is intended to indicate a compound having a mesogenic skeleton. It does not have to show sex.
  • the polymerizable composition can be polymerized (formed into a film) by performing a polymerization treatment by irradiation with light such as ultraviolet rays or heating.
  • the polymerizable compound having one or more polymerizable groups of the present invention has a characteristic that the birefringence of the compound is larger in the longer wavelength side than in the shorter wavelength side in the visible light region.
  • the in-plane retardation at a wavelength of 450 nm, Re (550 nm) indicates that the polymerizable compound having one or more polymerizable groups is placed on the substrate so that the long axis direction of the molecule is substantially horizontal to the substrate.
  • the birefringence need not be greater on the long wavelength side than on the short wavelength side in the ultraviolet region or infrared region.
  • the compound preferably contains at least one liquid crystalline compound selected from the group consisting of compounds represented by the following general formulas (1) to (7).
  • P 11 to P 74 represent a polymerizable group
  • S 11 to S 72 represent a spacer group or a single bond, and when a plurality of S 11 to S 72 are present, they may be the same or different
  • X 11 to X 72 are —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, — O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH
  • a 11 and A 12 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl.
  • the groups may be unsubstituted or substituted by one or more L 1 s , but when a plurality of A 11 and / or A 12 appear, they may be the same or different, Z 11 and Z 12 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO.
  • G is the following formula (G-1) to formula (G-6)
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and the alkyl group may be linear or branched, and any of the alkyl groups the hydrogen atoms may be substituted by a fluorine atom, one -CH 2 in the alkyl group - or nonadjacent two or more -CH 2 - are each independently -O -, - S- , —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO— or —C ⁇ C—.
  • W 81 represents a group having 5 to 30 carbon atoms having at least one aromatic group, and the group may be unsubstituted or substituted by one or more L 1
  • W 83 and W 84 each independently has 5 to 30 carbon atoms having a halogen atom, a cyano group, a hydroxy group, a nitro group, a carboxyl group, a carbamoyloxy group, an amino group, a sulfamoyl group, or at least one aromatic group.
  • alkyl groups having 1 to 20 carbon atoms alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, and 1 to 20 carbon atoms.
  • the above —CH 2 — is independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—.
  • G represents Formula (G-6);
  • L 1 is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino.
  • R 11 and R 31 are hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, cyano group, nitro group, isocyano group, thioisocyano group, or carbon number of 1 to 20
  • the alkyl group may be linear or branched, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.
  • One —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—.
  • m11 represents an integer of 0 to 8; ⁇ M7, n2 ⁇ n7, l4 ⁇ 16, k6 are each independently 0 5 of an integer.
  • each P— (SX) — is bonded to the existing A 11 and / or A 12 in the above formula (a).
  • the polymerizable groups P 11 to P 74 are represented by the following formulas (P-1) to (P-20).
  • these polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization and anionic polymerization.
  • the formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P ⁇ 7), formula (P-11), formula (P-13), formula (P-15) or formula (P-18) are preferred, and formula (P-1), formula (P-2), formula (P-18) P-7), formula (P-11) or formula (P-13) is more preferred, formula (P-1), formula (P-2) or formula (P-3) is more preferred, and formula (P- Particular preference is given to 1) or formula (P-2).
  • S 11 to S 72 represent a spacer group or a single bond. When a plurality of S 11 to S 72 are present, they may be the same or different. good.
  • the spacer group one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—, —C ⁇ C— or the following formula (S-1)
  • It preferably represents an alkylene group having 1 to 20 carbon atoms which may be replaced by
  • a plurality of S may be the same or different, and each independently represents one —CH 2 — or not adjacent 2
  • two or more —CH 2 — each independently represents an alkylene group having 1 to 10 carbon atoms or a single bond that may be independently replaced by —O—, —COO—, or —OCO—, each independently
  • an alkylene group having 1 to 10 carbon atoms or a single bond and when there are a plurality of alkylene groups, they may be the same or different and each independently an alkylene group having 1 to 8 carbon atoms. Is particularly preferred.
  • X 11 to X 72 are —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, — OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO— CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—
  • X 11 to X 72 When a plurality of X 11 to X 72 are present, they may be the same or different (provided that the P— (S—X) — bond includes -O-O- is not included.) From the viewpoint of easy availability of raw materials and ease of synthesis, when there are a plurality of them, they may be the same or different, and each independently represents —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 -, - OCO- CH 2 CH 2 -, - CH 2 CH 2 -COO -, - it is preferable to represent a CH 2 CH 2 -OCO- or a single bond, each independently -O -, - OCH 2 —, —CH 2 O—,
  • a 11 and A 12 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, Naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl Represents a group, these groups may be unsubstituted or substituted by one or more L, and when a plurality of A 11 and / or A 12 appear, they may be the same or different.
  • a 11 and A 12 are each independently an unsubstituted or 1,4-phenylene group that may be substituted with one or more L 1 , 1,4-cyclohexane from the viewpoint of availability of raw materials and ease of synthesis.
  • each group independently represents a group selected from formula (A-1) to formula (A-8), and each independently represents a group selected from formula (A-1). It is particularly preferable to represent a group selected from the formula (A-4).
  • Z 11 and Z 12 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—. , —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, — NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 -, -
  • Z 11 and Z 12 are each independently a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO— from the viewpoint of liquid crystallinity of the compound, availability of raw materials, and ease of synthesis.
  • M is the following formula (M-1) to formula (M-11)
  • M is each independently unsubstituted or substituted by one or more L 1 from the viewpoints of availability of raw materials and ease of synthesis, and the formula (M-1) or the formula (M-2) Alternatively, it preferably represents a group selected from unsubstituted formula (M-3) to (M-6), and may be unsubstituted or substituted by one or more L 1 . It is more preferable to represent a group selected from (M-2), and it is particularly preferable to represent a group selected from unsubstituted formula (M-1) or (M-2).
  • R 11 and R 31 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, or a nitro group.
  • An isocyano group, a thioisocyano group, or one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, Number of carbon atoms that may be substituted by —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO— or —C ⁇ C— 1 to 20 linear or branched alkyl groups are represented, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.
  • R 11 and R 31 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or one —CH 2 — or two or more not adjacent from the viewpoint of liquid crystallinity and ease of synthesis.
  • Each of —CH 2 — independently represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by —O—, —COO—, —OCO—, or —O—CO—O—.
  • It is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or more preferably a straight-chain alkyl group or straight-chain alkoxy group having 1 to 12 carbon atoms, and a straight-chain having 1 to 12 carbon atoms. It is particularly preferable to represent an alkyl group or a linear alkoxy group.
  • G represents a group selected from formula (G-1) to formula (G-6).
  • M is selected from Formula (M-1) to Formula (M-10)
  • G is selected from Formula (G-1) to Formula (G-5)
  • M is Formula (M-11).
  • G represents the formula (G-6), * in M and G represents a bond part, and two bonds other than * in M are Z 11 or A 11 present, and Z 12 present, respectively. or linked to a 12.
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group may be linear or branched. may even, any hydrogen atom in the alkyl group may be substituted by a fluorine atom, one -CH 2 in the alkyl group - or nonadjacent two or more -CH 2 - is Each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, It may be substituted by —NH—CO— or —C ⁇ C—.
  • W 81 represents a group having 5 to 30 carbon atoms having at least one aromatic group, and the group is unsubstituted or one May be substituted by the above L 1 ,
  • W 82 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and the alkyl group may be linear or branched.
  • Any hydrogen atom in the alkyl group may be substituted with a fluorine atom and / or —OH, and one —CH 2 — or two or more non-adjacent ones in the alkyl group
  • Each of —CH 2 — independently represents —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, May be substituted by —CF ⁇ CF— or —C ⁇ C—, or W 82 may represent the same meaning as W 81 In addition, W 81 and W 82 may form a ring structure together.
  • the aromatic group contained in W 81 may be an aromatic hydrocarbon group or aromatic heterocyclic group may contain both. These aromatic groups may be bonded via a single bond or a linking group (—OCO—, —COO—, —CO—, —O—), and may form a condensed ring. W 81 may contain an acyclic structure and / or a cyclic structure other than the aromatic group in addition to the aromatic group. From the viewpoint of availability of raw materials and ease of synthesis, the aromatic group contained in W 81 is unsubstituted or may be substituted with one or more L 1 from the following formula (W-1) Formula (W-19)
  • these groups have at least one bond at an arbitrary position, and may form a group in which two or more aromatic groups selected from these groups are linked by a single bond, Q 1 represents —O—, —S—, —NR 4 — (wherein R 4 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) or —CO—, and these aromatic groups In which —CH ⁇ may be independently replaced by —N ⁇ , and —CH 2 — is each independently —O—, —S—, —NR 4 — (wherein R 4 is a hydrogen atom Or represents an alkyl group having 1 to 8 carbon atoms), or may be replaced by —CO—, but does not include an —O—O— bond, and the group represented by the formula (W-1) includes: A group selected from the following formulas (W-1-1) to (W-1-8) which may be unsubstituted or substituted by one or more L 1 Is preferably represented.
  • these groups may have at least one bond at an arbitrary position.
  • the group represented by the formula (W-7) may be unsubstituted or substituted with one or more L 1 from the following formulas (W-7-1) to (W-7-7) It is preferable to represent a group selected from
  • these groups may have a bond at any one or more positions.
  • the group represented by the formula (W-10) the following formula (W-10-1) to the formula (W-10-8) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • W-11 the following formula (W-11-1) to the formula (W-11-13) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • Examples of the group represented by the formula (W-12) include the following formula (W-12-1) to formula (W-12-19) which may be unsubstituted or substituted with one or more L 1 groups. It is preferable to represent a group selected from
  • R 6 represents an alkyl group having from hydrogen or C 1 -C 8, R 6 is plurality of Each may be the same or different.
  • W-13 the following formula (W-13-1) to the formula (W-13-10) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • R 6 represents an alkyl group having from hydrogen or C 1 -C 8, R 6 is plurality of Each may be the same or different.
  • the group represented by the formula (W-14) may be unsubstituted or substituted with one or more L 1 from the following formulas (W-14-1) to (W-14-4) It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the group represented by the formula (W-15) may be unsubstituted or substituted with one or more L 1 from the following formulas (W-15-1) to (W-15-18) It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • W-16 the following formula (W-16-1) to the formula (W-16-4) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • W-17 the following formula (W-17-1) to the formula (W-17-6) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • these groups may have at least one bond at any position, and R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the group represented by the formula (W-18) is selected from the following formulas (W-18-1) to (W-18-6) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent the group.
  • R 6 represents an alkyl group having from hydrogen or C 1 -C 8, R 6 is plurality of Each may be the same or different.
  • W-19 the following formula (W-19-1) to the formula (W-19-9) which may be unsubstituted or substituted by one or more L 1 groups. It is preferable to represent a group selected from
  • R 6 represents an alkyl group having from hydrogen or C 1 -C 8, R 6 is plurality of Each may be the same or different.
  • the aromatic group contained in W 81 is unsubstituted or may be substituted by one or more L 1.
  • W 82 may be a hydrogen atom, or any hydrogen atom in the group may be substituted with a fluorine atom and / or —OH, and one —CH 2 Or two or more non-adjacent —CH 2 — are each independently —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—COO— , —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —CF ⁇ CF—, or carbon atom optionally substituted by —C ⁇ C— More preferably, it represents a linear or branched alkyl group of the formula 1 to 20, or a group represented by P W82 — (S W82 — (S W82 — (S W82 — (S W82 — (S W82 — (S W82 — (S W82 — (S W82 — (S W82 — (
  • W 82 represents a group having 2 to 30 carbon atoms having at least one aromatic group
  • W 82 represents a group selected from the above formulas (W-1) to (W-18) Is preferred. In that case, the more preferable structure is the same as described above.
  • W 82 represents a group represented by P W82 — (S W82 —X W82 ) n W82 —
  • preferred structures of the groups represented by P W82 , S W82 , and X W82 are This is the same as the preferred structure of the groups represented by 11 to P 74 , S 11 to S 72 , and X 11 to X 72 .
  • n W82 is preferably an integer of 0 to 3, more preferably 0 or 1.
  • terminal groups of the W 82 may be in the OH groups.
  • the cyclic group represented by —NW 81 W 82 may be unsubstituted or substituted with one or more L 1 It is preferable to represent a group selected from formulas (Wb-1) to (Wb-42).
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the cyclic group represented by —NW 81 W 82 is unsubstituted or one from the viewpoint of availability of raw materials and ease of synthesis.
  • the cyclic group represented by ⁇ CW 81 W 82 may be unsubstituted or substituted with one or more L 1 It is preferable to represent a group selected from formulas (Wc-1) to (Wc-81).
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and when a plurality of R 6 are present, they may be the same or different.
  • the cyclic group represented by ⁇ CW 81 W 82 is unsubstituted or 1 from the viewpoint of availability of raw materials and ease of synthesis.
  • the total number of ⁇ electrons contained in W 81 and W 82 is preferably 4 to 24 from the viewpoint of wavelength dispersion characteristics, storage stability, liquid crystallinity, and ease of synthesis.
  • W 83 and W 84 each independently has 5 to 30 carbon atoms having a halogen atom, a cyano group, a hydroxy group, a nitro group, a carboxyl group, a carbamoyloxy group, an amino group, a sulfamoyl group, or at least one aromatic group.
  • a cyano group, a carboxyl group, one —CH 2 — or two or more non-adjacent —C H 2 — is each independently substituted by —CO—, —COO—, —OCO—, —O—CO—O—, —CO—NH—, —NH—CO— or —C ⁇ C—
  • W84 is a cyano group, a nitro group, a carboxyl group, one —CH 2 — or adjacent group.
  • Two or more —CH 2 — that are not present are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O.
  • L 1 is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino.
  • L 1 represents a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or an arbitrary hydrogen.
  • the atom may be substituted with a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO.
  • L 1 represents a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom which may be substituted with a fluorine atom, one —CH 2 — or adjacent one.
  • No two or more —CH 2 — are each More preferably, it represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be independently substituted with a group independently selected from —O—, —COO— or —OCO—, and L 1 is More preferably, the fluorine atom, the chlorine atom, or an arbitrary hydrogen atom represents a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms which may be substituted with a fluorine atom, and L 1 is In particular, it represents a fluorine atom, a chlorine atom, or a linear alkyl group or linear alkoxy group having 1 to 8 carbon atoms.
  • m11 represents an integer of 0 to 8, and preferably represents an integer of 0 to 4 from the viewpoint of liquid crystallinity, availability of raw materials and ease of synthesis, and an integer of 0 to 2 Is more preferable, 0 or 1 is more preferable, and 1 is particularly preferable.
  • m2 to m7 each independently represents an integer of 0 to 5, but from the viewpoint of liquid crystallinity, availability of raw materials and ease of synthesis, 0 to 4 It is preferably an integer, more preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 1.
  • j11 and j12 each independently represent an integer of 1 to 5, but j11 + j12 represents an integer of 2 to 5. From the viewpoints of liquid crystallinity, ease of synthesis, and storage stability, j11 and j12 each independently preferably represent an integer of 1 to 4, more preferably an integer of 1 to 3, more preferably 1 or 2. It is particularly preferred to represent. j11 + j12 preferably represents an integer of 2 to 4.
  • the compound represented by the general formula (1) is preferably a compound represented by the following formula (1-a-1) to formula (1-a-108).
  • liquid crystalline compounds can be used alone or in combination of two or more.
  • the compound represented by the general formula (2) is preferably a compound represented by the following formula (2-a-1) to formula (2-a-65).
  • n represents an integer of 1 to 10.
  • liquid crystalline compounds can be used alone or in combination of two or more.
  • the compound represented by the general formula (4) is preferably a compound represented by the following formula (4-a-1) to (4-a-26).
  • liquid crystalline compounds can be used alone or in combination of two or more.
  • the compound represented by the general formula (5) is preferably a compound represented by the following formula (5-a-1) to formula (5-a-29).
  • n 1 to 10 carbon atoms.
  • the compound represented by the general formula (6) is preferably a compound represented by the following formula (6-a-1) to formula (6-a-25)
  • liquid crystalline compounds can be used alone or in combination of two or more. You can also.
  • the compound represented by the general formula (7) is preferably a compound represented by the following formula (7-a-1) to formula (7-a-26).
  • liquid crystalline compounds can be used alone or in combination of two or more.
  • the total content of the polymerizable compounds having one or two or more polymerizable groups is preferably 60 to 100% by mass based on the total amount of the polymerizable compounds used in the polymerizable composition, and is preferably 65 to 98%. More preferably, it is contained in an amount of 70 to 95% by mass.
  • the polymerizable composition of the present invention contains at least one non-liquid crystalline polymerizable compound.
  • the non-liquid crystalline polymerizable compound is preferably a compound having a molecular weight of 150 to 600 before polymerization.
  • An optical anisotropic body obtained by curing a polymerizable composition using a non-liquid crystalline polymerizable compound having a molecular weight of 150 to 600 before polymerization is preferable because of good haze. More preferably, a non-liquid crystalline polymerizable compound having a molecular weight of 160 to 580 before polymerization is used.
  • the polymerizable composition of the present invention is difficult to precipitate at room temperature by using the non-liquid crystalline polymerizable compound, can obtain a polymerizable composition excellent in orientation, and an optically anisotropic substance. When it does, haze of a coating film can be suppressed.
  • the non-liquid crystalline polymerizable compound preferably contains at least one selected from the group of compounds represented by the following general formula (II) having two or more polymerizable functional groups.
  • P 1 and P 2 each independently represent a polymerizable functional group
  • A represents an alkylene group having 1 to 30 carbon atoms
  • one or more —CH in the alkylene group 2 — may each independently be replaced by —O—, —CO—, tricyclodecane skeleton or bisphenol A skeleton, but does not include —O—O— bond
  • one or more of the alkylene group May be replaced by an alkyl group having 1 to 3 carbon atoms
  • k and l each independently represents an integer of 1 to 3.
  • P 1 and P 2 each independently represent a polymerizable functional group, and the following formulas (P-1) to (P-20)
  • these polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization and anionic polymerization.
  • the formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P ⁇ 7), formula (P-11), formula (P-13), formula (P-15) or formula (P-18) are preferred, and formula (P-1), formula (P-2), formula (P-18) P-7), formula (P-11) or formula (P-13) is more preferred, formula (P-1), formula (P-2) or formula (P-3) is more preferred, and formula (P- Particular preference is given to 1) or formula (P-2).
  • A represents an alkylene group having 1 to 30 carbon atoms, and one or more —CH 2 — in the alkylene group is each independently —O—, —CO—, tricyclo. It may be replaced with a decane skeleton or a bisphenol A skeleton, but does not include an —O—O— bond, and one or more hydrogen atoms in the alkylene group are replaced with an alkyl group having 1 to 3 carbon atoms. May be.
  • the A group is an alkylene having 1 to 30 carbon atoms in which one or more —CH 2 — in the alkylene group may be replaced by —O—, a tricyclodecane skeleton, or a bisphenol A skeleton.
  • a group is preferred, but one or more hydrogen atoms in the alkylene group may be replaced by an alkyl group having 1 to 3 carbon atoms.
  • the A group is more preferably an alkylene group having 1 to 26 carbon atoms in which one or more —CH 2 — in the alkylene group may be replaced by —O—, a tricyclodecane skeleton, or a bisphenol A skeleton.
  • one or more hydrogen atoms in the alkylene group may be replaced with an alkyl group having 1 to 3 carbon atoms.
  • the content of the non-liquid crystalline polymerizable compound represented by the general formula (II) is preferably 0.1 to 20% by mass with respect to the total amount of the polymerizable compound contained in the polymerizable composition of the present invention. ⁇ 10% by weight is particularly preferred. These can be used alone or in combination of two or more.
  • the polymerizable liquid crystal composition used in the present invention can contain an initiator as necessary.
  • the polymerization initiator used in the polymerizable composition of the present invention is used for polymerizing the polymerizable composition of the present invention.
  • the photopolymerization initiator used when the polymerization is carried out by light irradiation is not particularly limited, and known and conventional ones can be used as long as they do not inhibit the orientation state of the polymerizable compound.
  • a photoacid generator can be used as the photocationic initiator.
  • the photoacid generator include diazodisulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, and diphenyliodonium compounds.
  • the content of the photopolymerization initiator is preferably from 0.1 to 10% by mass, particularly preferably from 1 to 6% by mass, based on the total amount of the polymerizable compounds contained in the polymerizable composition. These can be used alone or in combination of two or more.
  • thermal polymerization initiator used in the thermal polymerization known ones can be used.
  • methyl acetoacetate peroxide cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl) Peroxydicarbonate, t-butylperoxybenzoate, methyl ethyl ketone peroxide, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, p-pentahydroperoxide, t-butylhydro
  • Organic peroxides such as peroxide, dicumyl peroxide, isobutyl peroxide, di (3-methyl-3-methoxybutyl) peroxydicarbonate, 1,1-bis (t-butylperoxy) cyclohexane, 2'-azobisisobutyronitrile, Azonitrile compounds such as 2,2′-azobis (2,4-dimethylvaleronitrile),
  • the content of the thermal polymerization initiator is preferably 0.1 to 10% by mass, particularly preferably 1 to 6% by mass. These can be used alone or in combination of two or more.
  • Organic solvent Organic solvent
  • the polymerizable composition of the present invention can contain an organic solvent as necessary. Although there is no limitation in particular as an organic solvent to be used, the organic solvent in which the said polymeric compound shows favorable solubility is preferable, and it is preferable that it is an organic solvent which can be dried at the temperature of 100 degrees C or less.
  • solvents examples include aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, cyclohexyl acetate, 3-butoxymethyl acetate, and ethyl lactate.
  • aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, cyclohexyl acetate, 3-butoxymethyl acetate, and ethyl lactate.
  • Ester solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, ether solvents such as tetrahydrofuran, 1,2-dimethoxyethane, anisole, N, N-dimethylformamide, N-methyl-2- Amido solvents such as pyrrolidone, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol monomethyl Propyl ether, diethylene glycol monomethyl ether acetate, .gamma.-butyrolactone and chlorobenzene, and the like.
  • ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone
  • ether solvents such as tetrahydrofuran,
  • the ratio of the organic solvent to be used is not particularly limited as long as the applied state is not significantly impaired since the polymerizable composition used in the present invention is usually applied, but the polymerizable content contained in the polymerizable composition is not limited.
  • the amount is preferably 50 to 700 parts by weight, more preferably 100 to 650 parts by weight, and particularly preferably 150 to 600 parts by weight with respect to 100 parts by weight of the total compound content.
  • the polymerizable liquid crystalline compound when the polymerizable liquid crystalline compound is dissolved in an organic solvent, it is preferable to stir with heating in order to dissolve it uniformly.
  • the heating temperature at the time of heating and stirring may be appropriately adjusted in consideration of the solubility of the polymerizable liquid crystal compound to be used in the organic solvent, but is preferably 15 ° C. to 130 ° C., more preferably 30 ° C. to 110 ° C. from the viewpoint of productivity. 50 ° C. to 100 ° C. is particularly preferable.
  • general-purpose additives can be used according to each purpose.
  • polymerization inhibitors for example, polymerization inhibitors, antioxidants, UV absorbers, leveling agents, alignment control agents, chain transfer agents, infrared absorbers, thixotropic agents, antistatic agents, dyes, fillers, chiral compounds, non-liquid crystals having polymerizable groups
  • Additives such as liquid crystalline compounds, other liquid crystal compounds, and alignment materials can be added to the extent that the alignment of the liquid crystal is not significantly reduced.
  • the polymerizable composition used in the present invention can contain a polymerization inhibitor as necessary. There is no limitation in particular as a polymerization inhibitor to be used, A well-known usual thing can be used.
  • N'-diphenyl-p-phenylenediamine Ni-propyl-N'-phenyl-p-phenylenediamine, N- (1.3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N.I.
  • Amine compounds such as N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl- ⁇ -naphthylamine, 4.4′-dicumyl-diphenylamine, 4.4′-dioctyl-diphenylamine, phenothiazine, Thioether compounds such as distearyl thiodipropionate, N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, ⁇ -nitroso- ⁇ -naphthol N, N-dimethyl p-nitrosoaniline, p-nitrosodiphenylamine, p-nitronedimethylamine, p-nitrone-N, N-diethylamine, N
  • the addition amount of the polymerization inhibitor is preferably 0.01 to 1.0% by mass and preferably 0.05 to 0.5% by mass with respect to the total amount of the polymerizable compounds contained in the polymerizable composition. Is more preferable.
  • the polymerizable composition used in the present invention can contain an antioxidant and the like as necessary. Examples of such compounds include hydroquinone derivatives, nitrosamine polymerization inhibitors, hindered phenol antioxidants, and more specifically, tert-butyl hydroquinone, “Q-1300” manufactured by Wako Pure Chemical Industries, Ltd.
  • the addition amount of the antioxidant is preferably 0.01 to 2.0% by mass, and preferably 0.05 to 1.0% by mass with respect to the total amount of the polymerizable compounds contained in the polymerizable composition. Is more preferable.
  • the polymerizable composition used in the present invention can contain an ultraviolet absorber and a light stabilizer as necessary. Although the ultraviolet absorber and light stabilizer to be used are not particularly limited, those which improve light resistance such as an optical anisotropic body and an optical film are preferable.
  • UV absorber examples include 2- (2-hydroxy-5-t-butylphenyl) -2H-benzotriazole “Tinuvin PS”, “Tinuvin 99-2”, “Tinuvin 109”, “TINUVIN 213”, “TINUVIN 234”, “TINUVIN 326”, “TINUVIN 328”, “TINUVIN 329”, “TINUVIN 384-2”, “TINUVIN 571”, 2- (2H-benzotriazol-2-yl) -4,6-bis (1-Methyl-1-phenylethyl) phenol “TINUVIN 900”, 2- (2H-benzotriazol-2-yl) -6- (1-methyl-1-phenylethyl) -4- (1,1,3 , 3-tetramethylbutyl) phenol “TINUVIN 928”, TINUVIN 1130, TINUVIN 400, TINUVIN 405, 2,4-bis [2-hydroxy-4-butoxyphenyl] -6- (2,4-dibutoxyphenyl) -1
  • Examples of the light stabilizer include “TINUVIN 111FDL”, “TINUVIN 123”, “TINUVIN 144”, “TINUVIN 152”, “TINUVIN 292”, “TINUVIN 622”, “TINUVIN 770”, “TINUVIN 765”, “TINUVIN 780”.
  • the polymerizable composition of the present invention can contain a leveling agent as necessary.
  • the leveling agent to be used is not particularly limited, but a leveling agent is preferably used in order to reduce film thickness unevenness when forming a thin film such as an optical anisotropic body or an optical film.
  • Examples of the leveling agent include alkyl carboxylates, alkyl phosphates, alkyl sulfonates, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, polyoxyethylene derivatives, fluoroalkylethylene oxide derivatives, polyethylene Examples include glycol derivatives, alkyl ammonium salts, and fluoroalkyl ammonium salts.
  • the addition amount of the leveling agent is preferably 0.01 to 2% by mass, and 0.05 to 0.5% by mass with respect to the total amount of the polymerizable compounds used in the polymerizable composition of the present invention. It is more preferable.
  • the polymerizable composition used in the present invention can contain an alignment controller in order to control the alignment state of the polymerizable compound.
  • the alignment control agent to be used include those in which the liquid crystalline compound is substantially horizontally aligned, substantially vertically aligned, or substantially hybridly aligned with respect to the substrate.
  • a chiral compound when a chiral compound is added, those which are substantially planarly oriented can be mentioned. As described above, horizontal alignment and planar alignment may be induced by the surfactant, but there is no particular limitation as long as each alignment state is induced, and a known and conventional one should be used. Can do.
  • a weight average molecular weight having a repeating unit represented by the following general formula (8) having an effect of effectively reducing the tilt angle of the air interface when an optical anisotropic body is used Is a compound having a molecular weight of 100 or more and 1000000 or less.
  • R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one hydrocarbon atom in the hydrocarbon group
  • R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one hydrocarbon atom in the hydrocarbon group
  • R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one hydrocarbon atom in the hydrocarbon group
  • a rod-like liquid crystal compound modified with a fluoroalkyl group a discotic liquid crystal compound, a polymerizable compound containing a long-chain aliphatic alkyl group which may have a branched structure, and the like are also included.
  • the polymerizable composition used in the present invention can contain a chain transfer agent in order to further improve the adhesion between the polymer or optical anisotropic body and the substrate.
  • Chain transfer agents include aromatic hydrocarbons, halogenated hydrocarbons such as chloroform, carbon tetrachloride, carbon tetrabromide, bromotrichloromethane, Mercaptan compounds such as octyl mercaptan, n-butyl mercaptan, n-pentyl mercaptan, n-hexadecyl mercaptan, n-tetradecyl merc, n-dodecyl mercaptan, t-tetradecyl mercaptan, t-dodecyl mercaptan, hexanedithiol, decandithiol 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhiogly
  • R 95 represents an alkyl group having 2 to 18 carbon atoms, and the alkyl group may be linear or branched, and one or more methylene groups in the alkyl group are oxygen atoms.
  • a sulfur atom that is not directly bonded to each other may be substituted with an oxygen atom, a sulfur atom, —CO—, —OCO—, —COO—, or —CH ⁇ CH—
  • R 96 is a carbon atom Represents an alkylene group of 2 to 18, and one or more methylene groups in the alkylene group are oxygen atoms, sulfur atoms, —CO—, —OCO—, wherein oxygen atoms and sulfur atoms are not directly bonded to each other.
  • —COO—, or —CH ⁇ CH— may be substituted.
  • the chain transfer agent is preferably added in a step of preparing a polymerizable solution by mixing a polymerizable compound in an organic solvent and heating and stirring, but it is added in a step of mixing a polymerization initiator in the subsequent polymerizable solution. It may be added in both steps.
  • the addition amount of the chain transfer agent is preferably 0.5 to 10% by mass, and preferably 1.0 to 5.0% by mass, based on the total amount of polymerizable compounds contained in the polymerizable composition. More preferred.
  • liquid crystal compounds that are not polymerizable can be added as necessary to adjust the physical properties.
  • a polymerizable compound having no liquid crystallinity is preferably added in the step of preparing a polymerizable solution by mixing the polymerizable compound with an organic solvent and stirring under heating. You may add in the process of mixing a polymerization initiator with a solution, and may add in both processes. The amount of these compounds added is preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 5% by mass or less, based on the polymerizable composition.
  • the polymerizable composition used in the present invention can contain an infrared absorber as necessary.
  • the infrared absorber to be used is not particularly limited, and any known and conventional one can be contained within a range not disturbing the orientation.
  • Examples of the infrared absorber include cyanine compounds, phthalocyanine compounds, naphthoquinone compounds, dithiol compounds, diimmonium compounds, azo compounds, and aluminum salts.
  • the polymerizable composition used in the present invention can contain an antistatic agent as necessary.
  • the antistatic agent to be used is not particularly limited, and a known and commonly used antistatic agent can be contained as long as the orientation is not disturbed.
  • an antistatic agent examples include a polymer compound having at least one sulfonate group or phosphate group in the molecule, a compound having a quaternary ammonium salt, a surfactant having a polymerizable group, and the like.
  • surfactants having a polymerizable group are preferred.
  • anionic surfactants such as “Antox SAD” and “Antox MS-2N” Made by company), “AQUALON KH-05”, “AQUALON KH-10”, “AQUALON KH-20”, “AQUALON KH-0530”, “AQUALON KH-1025” (above, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), Alkyl ethers such as “ADEKA rear soap SR-10N”, “ADEKA rear soap SR-20N” (manufactured by ADEKA Corporation), “Latemul PD-104” (manufactured by Kao Corporation), etc., “Latemuru S-120” “Latemul S-120A”, “Latemul S-180P”, “Latemul S-180A” (manufactured by Kao Corporation), “Eleminor” S-2 "(manufactureured by Kao Corporation), “Eleminor” S-2 "(
  • nonionic surfactants having a polymerizable group include, for example, “Antox LMA-20”, “Antox LMA-27”, “Antox EMH-20”, “Antox LMH— 20, “Antox SMH-20” (manufactured by Nippon Emulsifier Co., Ltd.), “Adekalia Soap ER-10”, “Adekalia Soap ER-20”, “Adekalia Soap ER-30”, “Adekalia Soap” ER-40 "(above, manufactured by ADEKA Corporation),” Latemul PD-420 “,” Latemuru PD-430 “,” Latemuru PD-450 “(above, manufactured by Kao Corporation), etc.
  • RN-10 Aqualon RN-20, Aqualon RN-30, Aqualon RN-50, Aqualon RN-2025 ( (Daiichi Kogyo Seiyaku Co., Ltd.), “Adekalia Soap NE-10”, “Adekalia Soap NE-20”, “Adekalia Soap NE-30”, “Adekalia Soap NE-40” (Meth) acrylate sulfuric acid such as alkylphenyl ether type or alkylphenyl ester type such as “RMA-564”, “RMA-568”, “RMA-1114” (above, manufactured by Nippon Emulsifier Co., Ltd.) An ester type is mentioned.
  • antistatic agents examples include polyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate, propoxypolyethylene glycol (meth) acrylate, and n-butoxypolyethylene glycol (meth) acrylate.
  • the antistatic agent can be used alone or in combination of two or more.
  • the amount of the antistatic agent added is preferably 0.001 to 10% by weight, more preferably 0.01 to 5% by weight, based on the total amount of the polymerizable compounds contained in the polymerizable composition.
  • the polymerizable composition used in the present invention can contain a dye as necessary.
  • the dye to be used is not particularly limited, and may include known and commonly used dyes as long as the orientation is not disturbed.
  • the dye examples include dichroic dyes and fluorescent dyes.
  • examples of such dyes include polyazo dyes, anthraquinone dyes, cyanine dyes, phthalocyanine dyes, perylene dyes, perinone dyes, squarylium dyes and the like.
  • the dye is preferably a liquid crystal dye. .
  • dichroic dye examples include the following formulas (d-1) to (d-8)
  • the addition amount of the dichroic dye or the like is preferably 0.001 to 10% by weight, more preferably 0.01 to 5% by weight, based on the total amount of the polymerizable compounds contained in the polymerizable composition. preferable.
  • the polymerizable composition used in the present invention can contain a filler as necessary.
  • the filler to be used is not particularly limited, and may contain known and commonly used fillers as long as the thermal conductivity of the obtained polymer is not lowered.
  • the filler examples include inorganic fillers such as alumina, titanium white, aluminum hydroxide, talc, clay, mica, barium titanate, zinc oxide, and glass fiber, metal powder such as silver powder and copper powder, aluminum nitride, and nitride.
  • thermally conductive fillers such as boron, silicon nitride, gallium nitride, silicon carbide, magnesia (aluminum oxide), alumina (aluminum oxide), crystalline silica (silicon oxide), fused silica (silicon oxide), silver nanoparticles, etc. Can be mentioned.
  • the polymerizable composition of the present invention may contain a chiral compound for the purpose of obtaining a chiral nematic phase.
  • the chiral compound itself does not need to exhibit liquid crystallinity, and may or may not have a polymerizable group.
  • the direction of the spiral of the chiral compound can be appropriately selected depending on the intended use of the polymer.
  • the chiral compound having a polymerizable group is not particularly limited and known and conventional compounds can be used, but a chiral compound having a large helical twisting power (HTP) is preferred.
  • the polymerizable group is preferably a vinyl group, a vinyloxy group, an allyl group, an allyloxy group, an acryloyloxy group, a methacryloyloxy group, a glycidyl group, or an oxetanyl group, and particularly preferably an acryloyloxy group, a glycidyl group, or an oxetanyl group.
  • the compounding amount of the chiral compound needs to be appropriately adjusted depending on the helical induction force of the compound, but it should be contained in an amount of 0.5 to 80% by mass based on the total amount of the liquid crystalline compound having a polymerizable group and the chiral compound.
  • the content is preferably 3 to 50% by mass, more preferably 5 to 30% by mass.
  • chiral compound examples include compounds represented by the following general formulas (10-1) to (10-4), but are not limited to the following general formulas.
  • Sp 5a and Sp 5b each independently represent an alkylene group having 0 to 18 carbon atoms, and the alkylene group is a carbon atom having one or more halogen atoms, CN groups, or polymerizable functional groups.
  • A5 and A6 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl
  • R 5a and R 5b represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, and the alkyl group may be substituted with one or more halogen atoms or CN.
  • R 5a and R 5b are represented by the general formula (10-a)
  • P 5a represents a polymerizable functional group
  • Sp 5a represents the same meaning as Sp 1
  • P 5a represents a substituent selected from the polymerizable groups represented by the following formulas (P-1) to (P-20).
  • chiral compound examples include compounds represented by the following general formulas (10-5) to (10-31).
  • n and n each independently represents an integer of 1 to 10
  • R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a fluorine atom. These may be the same or different.
  • chiral compound having no polymerizable group examples include, for example, pelargonic acid cholesterol having a cholesteryl group as a chiral group, cholesterol stearate, and a product of BDH having a 2-methylbutyl group as a chiral group.
  • the value obtained by dividing the thickness (d) of the polymer obtained by the helical pitch (P) in the polymer (d / P) is preferably added in an amount in the range of 0.1 to 100, and more preferably in an amount in the range of 0.1 to 20.
  • the polymerizable composition of the present invention may further contain a compound having a polymerizable group other than the general formula (II) but not a liquid crystal compound.
  • Such a compound can be used without particular limitation as long as it is generally recognized as a polymerizable monomer or polymerizable oligomer in this technical field.
  • the polymerizable composition used in the present invention can contain a liquid crystalline compound having one or more polymerizable groups in addition to the liquid crystalline compounds of the general formulas (1) to (7). However, if the amount added is too large, the retardation ratio may increase when used as a retardation plate. When added, the total amount of polymerizable compounds used in the polymerizable composition of the present invention may be increased. It is preferably 30% by mass or less, more preferably 10% by mass or less, and particularly preferably 5% by mass or less.
  • P 11 ⁇ P 74 represents a polymerizable group
  • S 11 ⁇ S 72 represents an a spacer group or a single bond
  • S 11 ⁇ S When a plurality of 72 are present, they may be the same or different
  • a 83 and A 84 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2.
  • Z 83 and Z 84 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO.
  • L 2 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino.
  • L 2 when a plurality of L 2 are present in the compound, they may be the same or different, m represents an integer of 0 to 8, and j83 and j84 each independently represents an integer of 0 to 5. J83 + j84 represents an integer of 1 to 5.
  • R 11 and R 31 are hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, cyano group, nitro group, isocyano group, thioisocyano group, or carbon number of 1 to 20
  • the alkyl group may be linear or branched, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.
  • One —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—.
  • m11 represents an integer of 0 to 8; ⁇ M7, n2 ⁇ n7, l4 ⁇ 16, k6 are each independently 0 5 of an integer.
  • general formula (7) is excluded from general formula (1).
  • P 11 to P 74 represent a polymerizable group, and the following formulas (P-1) to (P-20)
  • these polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization and anionic polymerization.
  • the formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P ⁇ 7), formula (P-11), formula (P-13), formula (P-15) or formula (P-18) are preferred, and formula (P-1), formula (P-2), formula (P-18) P-7), formula (P-11) or formula (P-13) is more preferred, formula (P-1), formula (P-2) or formula (P-3) is more preferred, and formula (P- Particular preference is given to 1) or formula (P-2).
  • S 11 to S 72 represent a spacer group or a single bond, and when a plurality of S 11 to S 72 are present, they may be the same It may be different.
  • the spacer group one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—, —C ⁇ C— or the following formula (S-1)
  • It preferably represents an alkylene group having 1 to 20 carbon atoms which may be replaced by
  • a plurality of S may be the same or different, and each independently represents one —CH 2 — or not adjacent 2
  • two or more —CH 2 — each independently represents an alkylene group having 1 to 10 carbon atoms or a single bond that may be independently replaced by —O—, —COO—, or —OCO—, each independently
  • an alkylene group having 1 to 10 carbon atoms or a single bond and when there are a plurality of alkylene groups, they may be the same or different and each independently an alkylene group having 1 to 8 carbon atoms. Is particularly preferred.
  • X 11 to X 72 are —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH— , —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO
  • each P— (SX) — is bonded to the existing A 83 and / or A 84 in the above formula (b). .
  • Specific examples of the compound represented by the general formula (1-b) include compounds represented by the following formulas (1-b-1) to (1-b-39).
  • R 111 and R 112 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a fluorine atom.
  • R 113 is a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, cyano group, nitro group, isocyano group, thioisocyano group, or one —CH 2 — or adjacent Two or more —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—.
  • Specific examples of the compound represented by the general formula (2-b) include compounds represented by the following formulas (2-b-1) to (2-b-34).
  • n and n each independently represents an integer of 1 to 18, and R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group.
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group.
  • these groups are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, they may be all unsubstituted or substituted with one or more halogen atoms.
  • These liquid crystal compounds can be used alone or in combination of two or more.
  • Specific examples of the compound represented by the general formula (3-b) include compounds represented by the following formulas (3-b-1) to (3-b-16).
  • liquid crystalline compounds can be used alone or in combination of two or more.
  • Specific examples of the compound represented by the general formula (4-b) include compounds represented by the following formulas (4-b-1) to (4-b-29).
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group.
  • these groups are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, they may be all unsubstituted or substituted with one or more halogen atoms.
  • These liquid crystalline compounds can be used alone or in combination of two or more.
  • Specific examples of the compound represented by the general formula (5-b) include compounds represented by the following formulas (5-b-1) to (5-b-26).
  • each n independently represents an integer of 1 to 10.
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group.
  • the group is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of them may be unsubstituted or may be substituted with one or more halogen atoms.
  • These liquid crystalline compounds can be used alone or in combination of two or more.
  • Specific examples of the compound represented by the general formula (6-b) include compounds represented by the following formulas (6-b-1) to (6-b-23).
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, In the case where these groups are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, they are all unsubstituted or substituted by one or more halogen atoms. May be.
  • These liquid crystalline compounds can be used alone or in combination of two or more.
  • Specific examples of the compound represented by the general formula (7-b) include compounds represented by the following formulas (7-b-1) to (7-b-25).
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group. These groups are alkyl groups having 1 to 6 carbon atoms, or carbon atoms. In the case of the alkoxy groups of 1 to 6, all may be unsubstituted, or may be substituted by one or more halogen atoms.) These liquid crystalline compounds may be used alone. It can also be used in combination of two or more. (Orientation material)
  • the polymerizable composition of the present invention may contain an alignment material that improves the orientation in order to improve the orientation.
  • the alignment material to be used may be a known and usual one as long as it is soluble in a solvent capable of dissolving the liquid crystalline compound having a polymerizable group used in the polymerizable composition of the present invention. It can be added as long as the orientation is not significantly deteriorated. Specifically, it is preferably 0.05 to 30% by weight, more preferably 0.5 to 15% by weight, and more preferably 1 to 10% by weight based on the total amount of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. Particularly preferred.
  • the alignment material is polyimide, polyamide, BCB (Penzocyclobutene Polymer), polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, epoxy acrylate resin, acrylic Resin, coumarin compound, chalcone compound, cinnamate compound, fulgide compound, anthraquinone compound, azo compound, arylethene compound, and other compounds that can be photoisomerized or photodimerized, but materials that are oriented by UV irradiation or visible light irradiation (Photo-alignment material) is preferable.
  • photo-alignment material examples include polyimide having a cyclic cycloalkane, wholly aromatic polyarylate, polyvinyl cinnamate as disclosed in JP-A-5-232473, polyvinyl ester of paramethoxycinnamic acid, and JP-A-6-6. 287453, cinnamate derivatives as shown in JP-A-6-289374, maleimide derivatives as shown in JP-A-2002-265541, and the like. Specifically, compounds represented by the following formulas (12-1) to (12-10) are preferable.
  • R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group, a nitro group
  • R ′ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. May be linear or branched, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and one —CH 2 — or adjacent group in the alkyl group may be substituted.
  • two or more —CH 2 — groups independently represent —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—.
  • the polymer of the present invention is obtained by polymerizing the polymerizable composition of the present invention in a state containing an initiator.
  • the polymer of the present invention is used for optical anisotropic bodies, retardation films, lenses, colorants, printed materials and the like.
  • optical anisotropic body manufacturing method (Optical anisotropic)
  • the polymerizable composition of the present invention is coated on a substrate or a substrate having an alignment function, and the liquid crystal molecules in the polymerizable liquid crystal composition of the present invention are uniformly retained in a nematic phase or a smectic phase.
  • the optical anisotropic body of the present invention is obtained by orienting and polymerizing.
  • the base material used for the optical anisotropic body of the present invention is a base material usually used for liquid crystal display elements, organic light emitting display elements, other display elements, optical components, colorants, markings, printed matter and optical films, If it is the material which has heat resistance which can endure the heating at the time of drying after application
  • base materials include glass base materials, metal base materials, ceramic base materials, plastic base materials, and organic materials such as paper.
  • the substrate when the substrate is an organic material, examples thereof include cellulose derivatives, polyolefins, polyesters, polyolefins, polycarbonates, polyacrylates, polyarylates, polyether sulfones, polyimides, polyphenylene sulfides, polyphenylene ethers, nylons, and polystyrenes.
  • plastic substrates such as polyester, polystyrene, polyolefin, cellulose derivatives, polyarylate, and polycarbonate are preferable.
  • a shape of a base material you may have a curved surface other than a flat plate. These base materials may have an electrode layer, an antireflection function, and a reflection function as needed.
  • surface treatment of these substrates may be performed.
  • the surface treatment include ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like.
  • an organic thin film, an inorganic oxide thin film, a metal thin film, etc. are provided on the surface of the substrate by a method such as vapor deposition, or in order to add optical added value.
  • the material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a color filter, or the like.
  • the base material may be subjected to a normal orientation treatment or may be provided with an orientation film so that the polymerizable composition is oriented when the polymerizable composition of the present invention is applied and dried.
  • the alignment treatment include stretching treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, oblique deposition treatment of SiO 2 on the substrate, and the like.
  • Such alignment films include polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, epoxy acrylate resin, acrylic resin, azo compound, coumarin.
  • Examples thereof include compounds such as compounds, chalcone compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds and arylethene compounds, and polymers and copolymers of the above compounds.
  • the compound subjected to the alignment treatment by rubbing is preferably an alignment treatment or a compound in which crystallization of the material is promoted by inserting a heating step after the alignment treatment.
  • liquid crystal molecules when a liquid crystal composition is brought into contact with a substrate having an alignment function, the liquid crystal molecules are aligned along the direction in which the substrate is aligned in the vicinity of the substrate. Whether the liquid crystal molecules are aligned horizontally with respect to the substrate or inclined or perpendicular to the substrate is greatly influenced by the alignment treatment method for the substrate. For example, when an alignment film having a very small pretilt angle as used in an in-plane switching (IPS) type liquid crystal display element is provided on a substrate, a polymerizable liquid crystal layer aligned substantially horizontally can be obtained.
  • IPS in-plane switching
  • Application methods for obtaining the optical anisotropic body of the present invention include applicator method, bar coating method, spin coating method, roll coating method, direct gravure coating method, reverse gravure coating method, flexo coating method, ink jet method, and die coating. Methods, cap coating methods, dip coating methods, slit coating methods, spray coating methods, and the like can be used. After applying the polymerizable composition, it is dried.
  • the liquid crystal molecules in the polymerizable composition of the present invention are preferably uniformly aligned while maintaining the smectic phase or nematic phase.
  • One of the methods is a heat treatment method. Specifically, after coating the polymerizable composition of the present invention on a substrate, the N (nematic phase) -I (isotropic liquid phase) transition temperature (hereinafter abbreviated as the NI transition temperature) of the liquid crystal composition. ) By heating to the above, the liquid crystal composition is brought into an isotropic liquid state. From there, it is gradually cooled as necessary to develop a nematic phase.
  • a heat treatment may be performed such that the temperature is maintained for a certain time within a temperature range in which the nematic phase of the polymerizable composition of the present invention is expressed.
  • the heating temperature is too high, the polymerizable liquid crystal compound may deteriorate due to an undesirable polymerization reaction. Moreover, when it cools too much, a polymeric composition raise
  • the liquid crystal phase is cooled to a minimum temperature at which phase separation does not occur, that is, is supercooled, and polymerization is performed in a state where the liquid crystal phase is aligned at the temperature.
  • the polymerization treatment of the dried polymerizable composition is generally performed by light irradiation such as visible ultraviolet rays or heating in a uniformly oriented state.
  • the polymerization is performed by light irradiation, specifically, it is preferable to irradiate visible ultraviolet light having a wavelength of 420 nm or less, and most preferable to irradiate ultraviolet light having a wavelength of 250 to 370 nm.
  • the polymerizable composition causes decomposition or the like due to visible ultraviolet light of 420 nm or less, it may be preferable to perform polymerization treatment with visible ultraviolet light of 420 nm or more.
  • Examples of the method for polymerizing the polymerizable composition of the present invention include a method of irradiating active energy rays and a thermal polymerization method.
  • the reaction proceeds at room temperature without requiring heating, and the active energy rays are irradiated.
  • a method of irradiating light such as ultraviolet rays is preferable because the operation is simple.
  • the temperature at the time of irradiation is preferably set to 30 ° C. or less as much as possible in order to avoid the induction of thermal polymerization of the polymerizable composition by setting the temperature at which the polymerizable composition of the present invention can maintain the liquid crystal phase.
  • the polymerizable liquid crystal composition usually has a temperature within the range from the C (solid phase) -N (nematic) transition temperature (hereinafter abbreviated as the CN transition temperature) to the NI transition temperature range during the temperature rising process. Shows liquid crystal phase.
  • the liquid crystal composition in a supercooled state is also included in the state in which the liquid crystal phase is retained. Specifically, irradiation with ultraviolet light of 390 nm or less is preferable, and irradiation with light having a wavelength of 250 to 370 nm is most preferable.
  • the polymerizable composition causes decomposition or the like due to ultraviolet light of 390 nm or less
  • This light is preferably diffused light and unpolarized light.
  • Ultraviolet irradiation intensity in the range of 0.05kW / m 2 ⁇ 10kW / m 2 is preferred. In particular, the range of 0.2 kW / m 2 to 2 kW / m 2 is preferable. If UV intensity is less than 0.05 kW / m 2, it takes much time to complete the polymerization.
  • the liquid crystal molecules in the polymerizable composition tend to be photodegraded, or a large amount of polymerization heat is generated to increase the temperature during the polymerization. May change, and the retardation of the film after polymerization may be distorted.
  • the orientation state of the unpolymerized part is changed by applying an electric field, a magnetic field or temperature, and then the unpolymerized part is polymerized.
  • An optical anisotropic body having a plurality of regions having orientation directions can also be obtained.
  • the alignment was regulated in advance by applying an electric field, magnetic field or temperature to the unpolymerized polymerizable liquid crystal composition, and the state was maintained.
  • An optical anisotropic body having a plurality of regions having different orientation directions can also be obtained by irradiating light from above the mask and polymerizing it.
  • the optical anisotropic body obtained by polymerizing the polymerizable liquid crystal composition of the present invention can be peeled off from the substrate and used alone as an optical anisotropic body, or it can be used as an optical anisotropic body as it is without peeling off from the substrate. You can also In particular, since it is difficult to contaminate other members, it is useful when used as a laminated substrate or by being attached to another substrate.
  • the retardation film of the present invention contains the optical anisotropic body, and the liquid crystalline compound forms a uniform continuous alignment state with respect to the substrate, and is in-plane with respect to the substrate. It is only necessary to have biaxiality outside, in-plane and out-of-plane or in-plane.
  • an adhesive, an adhesive layer, an adhesive, an adhesive layer, a protective film, a polarizing film, or the like may be laminated.
  • a retardation film for example, a positive A plate in which a rod-like liquid crystalline compound is substantially horizontally aligned with respect to a base material, and a negative A plate in which a disk-like liquid crystalline compound is vertically uniaxially oriented with respect to a base material
  • a positive C plate in which rod-like liquid crystalline compounds are aligned substantially vertically with respect to the substrate, a rod-like liquid crystalline compound is cholesteric aligned with respect to the substrate, or a negative C in which disc-like liquid crystalline compounds are horizontally aligned uniaxially.
  • orientation mode of a plate, a biaxial plate, a positive O plate in which a rod-like liquid crystalline compound is hybrid-aligned with respect to a substrate, and a negative O plate in which a disc-like liquid crystalline compound is hybrid-aligned with respect to a substrate can be applied.
  • various orientation modes can be applied without particular limitation as long as the viewing angle dependency is improved.
  • orientation modes of positive A plate, negative A plate, positive C plate, negative C plate, biaxial plate, positive O plate, and negative O plate can be applied.
  • the positive A plate means an optical anisotropic body in which the polymerizable liquid crystal composition is homogeneously aligned.
  • a negative C plate means the optically anisotropic body which made the polymerizable liquid crystal composition the cholesteric orientation.
  • a positive A plate it is preferable to use a positive A plate as the first retardation layer in order to compensate the viewing angle dependence of polarization axis orthogonality and widen the viewing angle.
  • the positive A plate has a refractive index in the in-plane slow axis direction of the film as nx, a refractive index in the in-plane fast axis direction of the film as ny, and a refractive index in the thickness direction of the film as nz,
  • the positive A plate preferably has an in-plane retardation value in the range of 30 to 500 nm at a wavelength of 550 nm.
  • the thickness direction retardation value is not particularly limited.
  • the Nz coefficient is preferably in the range of 0.9 to 1.1.
  • a so-called negative C plate having negative refractive index anisotropy as the second retardation layer.
  • a negative C plate may be laminated on a positive A plate.
  • the negative C plate has a refractive index nx in the in-plane slow axis direction of the retardation layer, ny in the in-plane fast axis direction of the retardation layer, and a refractive index in the thickness direction of the retardation layer.
  • the thickness direction retardation value of the negative C plate is preferably in the range of 20 to 400 nm.
  • the refractive index anisotropy in the thickness direction is represented by a thickness direction retardation value Rth defined by the following formula (2).
  • a thickness direction retardation value Rth an in-plane retardation value R 0 , a retardation value R 50 measured with a slow axis as an inclination axis and an inclination of 50 °, a film thickness d, and an average refractive index n 0 of the film are used.
  • nx, ny, and nz can be obtained by numerical calculation from the equation (1) and the following equations (4) to (7), and these can be substituted into the equation (2).
  • R 0 (nx ⁇ ny) ⁇ d (1)
  • Rth [(nx + ny) / 2 ⁇ nz] ⁇ d (2)
  • Nz coefficient (nx ⁇ nz) / (nx ⁇ ny) (3)
  • R 50 (nx ⁇ ny ′) ⁇ d / cos ( ⁇ ) (4)
  • ny ′ ny ⁇ nz / [ny 2 ⁇ sin 2 ( ⁇ ) + nz 2 ⁇ cos 2 ( ⁇ )] 1/2 (7)
  • the numerical calculation shown here is automatically performed in the device, and the in-plane retardation value R0 , the thickness direction retardation value Rth, etc.
  • the polymerizable composition of the present invention is coated on a base material or a base material having an orientation function, or injected into a lens-shaped mold, and uniformly oriented while maintaining a nematic phase or a smectic phase. By polymerizing, it can be used for the lens of the present invention.
  • the shape of the lens include a simple cell type, a prism type, and a lenticular type.
  • the polymerizable composition of the present invention is coated on a substrate or a substrate having an alignment function, and is uniformly aligned and polymerized while maintaining a nematic phase or a smectic phase. It can be used for an element. Examples of usage forms include optical compensation films, patterned retardation films for liquid crystal stereoscopic display elements, retardation correction layers for color filters, overcoat layers, alignment films for liquid crystal media, and the like.
  • the liquid crystal display element has a liquid crystal medium layer, a TFT drive circuit, a black matrix layer, a color filter layer, a spacer, and a liquid crystal medium layer at least sandwiched by corresponding electrode circuits on at least two base materials.
  • the layer, the polarizing plate layer, and the touch panel layer are arranged outside the two substrates, but in some cases, the optical compensation layer, the overcoat layer, the polarizing plate layer, and the electrode layer for the touch panel are narrowed in the two substrates. May be held.
  • Alignment modes of liquid crystal display elements include TN mode, VA mode, IPS mode, FFS mode, OCB mode, etc.
  • a phase difference corresponding to the orientation mode is used.
  • the liquid crystalline compound in the polymerizable composition may be substantially horizontally aligned with the substrate.
  • a liquid crystalline compound having more polymerizable groups in one molecule may be thermally polymerized.
  • the organic light emitting display of the present invention can be used for an element.
  • it can be used as an antireflection film of an organic light emitting display element by combining the retardation film obtained by the polymerization and a polarizing plate.
  • the angle formed by the polarizing axis of the polarizing plate and the slow axis of the retardation film is preferably about 45 °.
  • the polarizing plate and the retardation film may be bonded together with an adhesive or a pressure-sensitive adhesive. Moreover, you may laminate
  • the polarizing plate used at this time may be in the form of a film doped with a pigment or in the form of a metal such as a wire grid.
  • a polymer obtained by polymerizing the polymerizable composition of the present invention in a nematic phase, a smectic phase, or in a state of being oriented on a substrate having an orientation function should be used as a heat dissipation material for an illumination element, particularly a light emitting diode element. You can also.
  • the form of the heat dissipation material is preferably a prepreg, a polymer sheet, an adhesive, a sheet with metal foil, or the like.
  • the polymerizable composition of the present invention can be used as the optical component of the present invention by polymerizing the polymerizable composition while maintaining a nematic phase or a smectic phase, or in combination with an alignment material.
  • the polymerizable composition of the present invention can be used as a colorant by adding a colorant such as a dye or an organic pigment.
  • the polymerizable composition of the present invention can be combined with or added to a dichroic dye, a lyotropic liquid crystal, a chromonic liquid crystal, or the like to be used as a polarizing film.
  • Example 1 After dissolution was confirmed, the solution was returned to room temperature, and Irgacure OXE-01 (OXE-01: BASF Japan Ltd.) 6 parts by company) and 0.2 parts by FTX-218 (FTX-218: made by Neos Co., Ltd.) were added and further stirred to obtain a solution. The solution was clear and uniform. The resulting solution was filtered through a 0.20 ⁇ m membrane filter to obtain the polymerizable composition (1) of Example 1.
  • Tables 1 to 12 below show specific compositions of the polymerizable compositions (1) to (80) of the present invention and the comparative polymerizable compositions (C1) to (C4).
  • Irgacure 907 Irg.907; manufactured by BASF
  • Irgacure OX-01 Irgacure OXE-01; manufactured by BASF
  • Irgacure TPO TPO; manufactured by BASF
  • Irganox 1076 I-1076; manufactured by BASF
  • CPN Cyclopentanone
  • TOL 1,1,2-trichloroethane
  • Example 81 The polyimide solution for alignment film was applied to a glass substrate having a thickness of 0.7 mm using a spin coating method, dried at 100 ° C. for 10 minutes, and then baked at 200 ° C. for 60 minutes to obtain a coating film. The obtained coating film was rubbed. The rubbing treatment was performed using a commercially available rubbing apparatus.
  • the polymerizable composition (1) of the present invention was applied to a rubbed substrate by a spin coating method and dried at a temperature (74 ° C.) of ⁇ 10 ° C. from the phase transition temperature (84 ° C.) for 2 minutes.
  • the obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp, to obtain the optical anisotropic body of Example 81.
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • the obtained optical anisotropic body was evaluated for orientation, retardation ratio, and haze according to the following criteria.
  • Orientation evaluation Double-circle: There is no defect visually and there is no defect also by polarization microscope observation.
  • ⁇ There are no defects visually, but a non-oriented portion exists in part by observation with a polarizing microscope.
  • ⁇ There are no defects visually, but there are non-oriented portions as a whole by observation with a polarizing microscope.
  • X Some defects are visually observed, and non-oriented portions are present as a whole by observation with a polarizing microscope.
  • Phase difference ratio When the retardation (phase difference) of the optical anisotropic body obtained as the evaluation sample was measured with a retardation film / optical material inspection apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.), an in-plane retardation at a wavelength of 550 nm ( Re (550)) was 121 nm. Further, the ratio Re (450) / Re (550) between the in-plane retardation (Re (450)) and Re (550) at a wavelength of 450 nm was 0.807, and a retardation film with good uniformity was obtained.
  • Example 82 to 154 The same conditions as in Example 81 were used, except that the polymerizable compositions used were changed to the polymerizable compositions (2) to (74) and comparative polymerizable compositions (C1) to (C4) of the present invention, respectively.
  • optical anisotropic bodies of Examples 82 to 154 and Comparative Examples 1 to 4 were obtained.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 150 The polymerizable composition (75) of the present invention was applied by a bar coating method to a film in which a silane coupling type vertical alignment film was laminated on a COP film substrate, and dried at 80 ° C. for 2 minutes. The obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at a conveyor speed of 6 m / min using a UV conveyor device (manufactured by GS Yuasa Co., Ltd.) to obtain an optical anisotropic body of Example 150. When the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homeotropic alignment. The obtained optical anisotropic body was evaluated for orientation, retardation ratio, and haze according to the following criteria. (Orientation evaluation) (Double-circle): There is no defect visually and there is no defect also by polarization microscope observation.
  • Orientation evaluation Double-circle
  • phase difference ratio The retardation (phase difference) of the optically anisotropic body obtained as the evaluation sample was measured with a retardation film / optical material inspection apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).
  • the phase difference (Rth (550)) was 36.5 nm.
  • the ratio Rth (450) / Rth (550) of retardation (Rth (450)) to Rth (550) in the film thickness direction at a wavelength of 450 nm is 0.871, and a retardation film with good uniformity can be obtained. It was.
  • Example 151 to 153 The optical composition having homeotropic alignment in Examples 151 to 153 under the same conditions as in Example 150, except that the polymerizable compositions used were changed to the polymerizable compositions (76) to (78) of the present invention, respectively. I got a cuboid.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were performed in the same manner as in Example 150.
  • Example 154 A uniaxially stretched PET film having a thickness of 50 ⁇ m was rubbed using a commercially available rubbing apparatus, and then the polymerizable composition (79) of the present invention was applied by a bar coating method and dried at 80 ° C. for 2 minutes. The obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at a conveyor speed of 6 m / min using a UV conveyor device (manufactured by GS Yuasa Co., Ltd.). Obtained. The orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 155 An optical anisotropic body having the hybrid orientation of Example 155 was obtained under the same conditions as Example 154 except that the polymerizable composition used was changed to the polymerizable composition (80) of the present invention.
  • the alignment evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were performed in the same manner as in Example 154. The obtained results are shown in Table 20 below.
  • Example 156 A uniaxially stretched PET film having a thickness of 50 ⁇ m was rubbed using a commercially available rubbing apparatus, and then the polymerizable composition (2) of the present invention was applied by a bar coating method and dried at 80 ° C. for 2 minutes. The obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at a conveyor speed of 6 m / min using a UV conveyor device (manufactured by GS Yuasa Co., Ltd.). Obtained. The orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 156 except that the polymerizable composition used was changed to the polymerizable composition (16), (23), (27), (28), (30), (40), and (41) of the present invention, respectively.
  • the optical anisotropic bodies of Examples 157 to 163 were obtained under the same conditions as those described above.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 164 5 parts of a photoalignment material (weight average molecular weight: 200,000) represented by the following formula (12-4) was dissolved in 95 parts of cyclopentanone to obtain a solution.
  • the obtained solution was filtered with a 0.45 ⁇ m membrane filter to obtain a photo-alignment solution (1).
  • a membrane (1) was obtained.
  • the polymerizable composition (2) was applied on the obtained photo-alignment film by a spin coating method and dried at 90 ° C. for 2 minutes.
  • the obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp, to obtain an optical anisotropic body of Example 164.
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 165 5 parts of a photoalignment material represented by the following formula (12-9) is dissolved in 95 parts of N-methyl-2-pyrrolidone, and the resulting solution is filtered through a 0.45 ⁇ m membrane filter to obtain a photoalignment solution (2 ) Next, it was applied to a glass substrate having a thickness of 0.7 mm by using a spin coating method, dried at 100 ° C. for 5 minutes, further dried at 130 ° C. for 10 minutes, and immediately converted to 313 nm linearly polarized light at 50 mW / cm 2. The photo-alignment film (2) was obtained by irradiating with an intensity of 10 seconds.
  • the polymerizable composition (16) was applied on the obtained photo-alignment film by a spin coating method and dried at 90 ° C. for 2 minutes.
  • the obtained coating film was cooled to room temperature and then irradiated with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp to obtain the optical anisotropic body of Example 165.
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 166 1 part of the photo-alignment material represented by the above formula (12-10) is dissolved in 50 parts of (2-ethoxyethoxy) ethanol and 49 parts of 2-butoxyethanol, and the resulting solution is filtered through a 0.45 ⁇ m membrane filter. As a result, a photoalignment solution (3) was obtained. Next, it was applied to a polymethyl methacrylate (PMMA) film having a thickness of 80 ⁇ m using a bar coating method, dried at 80 ° C. for 2 minutes, and irradiated with 365 nm linearly polarized light at an intensity of 50 mW / cm 2 for 10 seconds. A photo-alignment film (3) was obtained.
  • PMMA polymethyl methacrylate
  • the polymerizable composition (23) was applied on the obtained photo-alignment film by a spin coating method and dried at 80 ° C. for 2 minutes.
  • the obtained coating film was cooled to room temperature and then irradiated with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp to obtain the optical anisotropic body of Example 166.
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 167 A uniaxially stretched PET film having a thickness of 50 ⁇ m was rubbed using a commercially available rubbing apparatus, and then the polymerizable composition (42) of the present invention was applied by a bar coating method and dried at 100 ° C. for 2 minutes. The obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at a conveyor speed of 6 m / min using a UV conveyor device (manufactured by GS Yuasa Co., Ltd.) to obtain an optical anisotropic body of Example 167. When the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • Example 168 to 169 Optical anisotropic bodies of Examples 168 and 169 were obtained under the same conditions as in Example 167 except that the polymerizable composition used was changed to the polymerizable compositions (43) and (44) of the present invention, respectively. .
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, all were homogeneous orientations.
  • the orientation evaluation, retardation ratio, and haze evaluation of the obtained optical anisotropic body were carried out in the same manner as in Example 81.
  • Example 170 The polyimide solution for alignment film was applied to a glass substrate having a thickness of 0.7 mm using a spin coating method, dried at 100 ° C. for 10 minutes, and then baked at 200 ° C. for 60 minutes to obtain a coating film. The obtained coating film was rubbed. The rubbing treatment was performed using a commercially available rubbing apparatus.
  • the polymerizable composition (64) of the present invention was applied to a rubbed substrate by a spin coating method and dried at 80 ° C. for 2 minutes.
  • the obtained coating film was cooled to room temperature, and then irradiated with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp, to obtain the optical anisotropic body of Example 170.
  • the obtained optical anisotropic body was visually confirmed under crossed Nicols, it was homogeneous orientation.
  • the obtained optical anisotropic body has a phase difference Re (550) of 137 nm and an in-plane phase difference (Re (450)) / Re (550) ratio Re (450) / Re (550) of 0.865 at a wavelength of 450 nm.
  • a retardation film with good uniformity was obtained.
  • the repellency of the obtained optical anisotropic body (102) was visually observed, no unevenness was observed in the coating film, and the haze was 0.22.
  • a polyvinyl alcohol film having an average degree of polymerization of about 2400 and a saponification degree of 99.9 mol% or more and a thickness of 75 ⁇ m was uniaxially stretched about 5.5 times in a dry manner, and further kept at 60 ° C.
  • After being immersed in pure water for 60 seconds it was immersed in an aqueous solution having a weight ratio of iodine / potassium iodide / water of 0.05 / 5/100 at 28 ° C. for 20 seconds. Then, it was immersed in an aqueous solution having a weight ratio of potassium iodide / boric acid / water of 8.5 / 8.5 / 100 at 72 ° C. for 300 seconds.
  • the film was washed with pure water at 26 ° C. for 20 seconds and then dried at 65 ° C. to obtain a polarizing film in which iodine was adsorbed and oriented on a polyvinyl alcohol resin.
  • the antireflection film of the present invention was obtained by laminating with an adhesive so that the angle between the polarization axis of the obtained polarizing film and the slow axis of the optical anisotropic body of Example 170 was 45 °. Furthermore, when the obtained antireflection film and an aluminum plate used as an alternative to the organic light-emitting element were bonded together with an adhesive, the reflection visibility coming from the aluminum plate was visually confirmed from the front and oblique 45 °. No plate-derived transfer was observed.
  • the polymerizable composition using at least one of the general formula (II) is excellent in solubility and storage stability and has a polymerizable liquid crystal composition.
  • the optical anisotropic bodies (Examples 81 to 170) formed from the products (1) to (80) all have good orientation evaluation and haze evaluation results, and can be said to be excellent in productivity.
  • the polymerizable liquid crystal compositions using the general formulas (II-1), (II-8), and (II-9) showed very good results for evaluation of alignment and evaluation of coating unevenness. .
  • Comparative Examples 1 to 4 when a compound that did not satisfy the provisions of the present invention was used, the alignment evaluation result was poor and was inferior to the polymerizable liquid crystal composition of the present invention.

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  • Physics & Mathematics (AREA)
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  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne une composition polymérisable qui a une faible tendance à se déposer à température ambiante après séchage par solvant, présente d'excellentes propriétés d'orientation, et a des propriétés de dispersion chromatique inverse ou des propriétés de dispersion chromatique faible. La présente invention concerne, en outre, une composition polymérisable dans laquelle le trouble ne tend pas à se former lorsqu'une substance polymérisée en forme de film obtenue par polymérisation de la composition est produite. En outre, la présente invention consiste à fournir : un corps optiquement anisotrope, un film à différence de phase, un film de compensation optique, un film antiréfléchissant, une lentille, et une feuille de lentille comprenant la composition polymérisable; et un élément d'affichage à cristaux liquides, un élément d'affichage électroluminescent organique, un élément d'éclairage, un composant optique, un colorant, un marquage de sécurité, un élément d'émission laser, un film polarisant, un matériau colorant, une matière imprimée, etc., dans lequel la composition polymérisable est utilisée. La présente invention concerne une composition polymérisable contenant a) un composé de cristaux liquides polymérisable qui a un ou plusieurs groupes polymérisables et répond à la formule (I) : Re (450 nm)/Re (550 nm) < 1,0 (I), et b) au moins un composé polymérisable non liquide ayant un poids moléculaire de 150 à 600.
PCT/JP2017/041786 2016-11-29 2017-11-21 Composition polymérisable et corps optiquement anisotrope dans lequel celui-ci est utilisé WO2018101122A1 (fr)

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JP2021002026A (ja) * 2019-06-21 2021-01-07 Dic株式会社 重合性液晶組成物、光学異方体及びその製造方法

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