WO2017170947A1 - Composition de formation de couche de polarisation - Google Patents

Composition de formation de couche de polarisation Download PDF

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Publication number
WO2017170947A1
WO2017170947A1 PCT/JP2017/013423 JP2017013423W WO2017170947A1 WO 2017170947 A1 WO2017170947 A1 WO 2017170947A1 JP 2017013423 W JP2017013423 W JP 2017013423W WO 2017170947 A1 WO2017170947 A1 WO 2017170947A1
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group
ring
carbon atoms
side chain
hydrogen atom
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PCT/JP2017/013423
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English (en)
Japanese (ja)
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伊藤　潤
裕太 菅野
佳代 稲見
真 畑中
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日産化学工業株式会社
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Priority to KR1020187027769A priority Critical patent/KR102263428B1/ko
Priority to CN201780020939.6A priority patent/CN109153857B/zh
Priority to JP2018509475A priority patent/JP7078903B2/ja
Publication of WO2017170947A1 publication Critical patent/WO2017170947A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L35/02—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present invention relates to a polarizing layer forming composition.
  • iodine has been widely used as a dichroic dye for polarizing plates used in liquid crystal displays and the like.
  • iodine-based polarizing films have a problem that heat resistance, light resistance, etc. are inferior, attempts have been made to use organic dichroic substances, that is, dichroic dyes.
  • a dichroic dye for the purpose of obtaining high dichroism, a dye having an azo skeleton as a basic skeleton (Patent Documents 1 and 2), a dye having an anthraquinone skeleton and the like are often used.
  • a dye serving as a guest material was mixed with a liquid crystal compound serving as a host material as a coating type polarizing plate.
  • a method of applying a liquid crystal composition to a substrate is known (Patent Document 3).
  • Patent Document 4 a method using a mixture of a crosslinkable liquid crystal and a polymerizable dichroic dye
  • adding a polymerizable non-liquid crystal solvent to the polymerizable liquid crystal compound A method for producing an optical anisotropic body in which a non-liquid crystal solvent is left in the coating film to improve adhesion with other optical films (Patent Document 5); and a polymerization property including a polymerizable mesogenic compound and a dichroic dye
  • Patent Document 6 a method in which a mesogen preparation is prepared and a polarizer is effectively prepared using the mesogen preparation in terms of time and cost.
  • a coating-type polarizing plate composed of a liquid crystal compound and a dichroic dye needs to align the liquid crystal compound in order to exhibit desired characteristics.
  • a liquid crystal alignment film is required in order to control alignment by applying a liquid crystal compound and a dichroic dye on a liquid crystal alignment film subjected to alignment treatment.
  • an object of the present invention is to provide a polarizing layer forming composition that does not require a liquid crystal alignment film and can produce a coating-type polarizing plate having desired characteristics.
  • A, B, and D are each independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO—.
  • S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be replaced by a halogen group;
  • T is a single bond or an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group;
  • Y 1 represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents 2 to 6 different rings are bonded to each other via a bonding group B, and the hydrogen atoms bonded to them are each independently —COOR 0 (wherein R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group), —NO 2
  • Y 2 is a group selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof,
  • the hydrogen atom bonded to each independently represents —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms.
  • R May be substituted with an alkyloxy group of R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or the same definition as Y 1 ;
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • X may be the same or different;
  • Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and the hydrogen atoms bonded thereto are independently —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH— May be substituted with CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • X is —CH ⁇ CH—CO—O— or —O—CO—CH ⁇ CH—
  • P or Q on the side to which —CH ⁇ CH— is bonded is an aromatic ring
  • l1 is 0 or 1
  • l2 is an integer from 0 to 2
  • A represents a single bond when T is a single bond
  • B represents a single bond when T is a single bond
  • H and I are each independently a group selected from a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, and combinations thereof.
  • ⁇ 4> The component according to any one of ⁇ 1> to ⁇ 3>, wherein the component (A) has any one liquid crystalline side chain selected from the group consisting of the following formulas (21) to (31): Combined composition.
  • A, B, q1 and q2 have the same definition as above;
  • Y 3 is a group selected from the group consisting of a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing heterocycle, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • Each hydrogen atom bonded thereto may be independently substituted with —NO 2 , —CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
  • R 3 is a hydrogen atom, —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, halogen group, monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing Represents a heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; l represents an integer of 1 to 12, m represents an integer of 0 to 2, provided that in the formulas (25) to (26), the sum of all m is 2 or more, and the formulas (27) to (28 ), The sum of all m
  • One or more hydrogen atoms in the carbocycle or heterocycle may be replaced with a fluorine atom or an organic group, and —CH 2 CH 2 — in R 106 is replaced with —CH ⁇ CH—.
  • R 106 may be replaced by phenylene or a divalent carbocyclic or heterocyclic ring, and when any of the following groups is not adjacent to each other: These groups may be substituted: —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, —CO—, wherein R 107 is a hydrogen atom or methyl Base .), And n represents 0 or 1.
  • ⁇ 6> A polarizing layer forming composition containing the polymer composition according to any one of ⁇ 1> to ⁇ 5> above.
  • a novel polymer composition suitable for obtaining a polarizing plate having high polarization performance can be provided.
  • the polymer composition used in the production method of the present invention has a photosensitive side chain polymer (hereinafter also simply referred to as a side chain polymer) capable of exhibiting liquid crystallinity and a dichroic dye.
  • the coating film obtained using the polymer composition is a film having a photosensitive side chain type polymer that can exhibit liquid crystallinity. This coating film is subjected to orientation treatment by irradiation with polarized light without being rubbed. And after polarized light irradiation, the side chain type polymer film is subjected to a heating process to become a coating film having polarization performance (hereinafter also referred to as a polarizing layer).
  • the polymer composition of the present invention is useful as a polarizing layer forming composition.
  • the component (A) is a side chain polymer having a structure that exhibits photoreactivity and a structure that exhibits liquid crystallinity, and is a photosensitive side chain polymer that can exhibit liquid crystallinity.
  • the side chain polymer preferably reacts with light in the wavelength range of 250 nm to 400 nm and exhibits liquid crystallinity in the temperature range of 60 ° C. to 300 ° C.
  • the (A) side chain polymer preferably has a photosensitive side chain that reacts with light in the wavelength range of 250 nm to 400 nm.
  • the (A) side chain polymer preferably has a mesogenic group in order to exhibit liquid crystallinity in the temperature range of 60 ° C to 300 ° C.
  • the side chain type polymer has a photosensitive side chain bonded to the main chain, and can cause a crosslinking reaction, an isomerization reaction, or a light fleece rearrangement in response to light.
  • the structure of the side chain having photosensitivity is not particularly limited, but a structure that undergoes a crosslinking reaction or photofleece rearrangement in response to light is desirable, and a structure that causes a crosslinking reaction is more desirable. In this case, even when exposed to external stress such as heat, the realized polarization performance can be stably maintained for a long period of time. Further, when the side chain polymer is used as a polarizing layer, it is preferable to have a rigid mesogenic component in the side chain structure from the viewpoint that stable polarization performance can be obtained.
  • the polymer structure has, for example, a main chain and a side chain bonded to the main chain, and the side chain includes a mesogenic component such as a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenylbenzoate group, and an azobenzene group, and a tip.
  • a mesogenic component such as a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenylbenzoate group, and an azobenzene group, and a tip.
  • More specific examples of the structure of the photosensitive side chain polymer film capable of exhibiting liquid crystallinity include hydrocarbon, (meth) acrylate, itaconate, fumarate, maleate, ⁇ -methylene- ⁇ -butyrolactone, styrene, A main chain composed of at least one selected from the group consisting of radically polymerizable groups such as vinyl, maleimide, norbornene and siloxane, and a side chain having photosensitivity and a side chain having liquid crystallinity bonded to each other It is preferable that
  • the side chain having photosensitivity is preferably a structure having a side chain composed of at least one of the following formulas (1) to (6).
  • A, B, and D are each independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO—.
  • S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be replaced by a halogen group;
  • T is a single bond or an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group;
  • Y 1 represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents 2 to 6 different rings are bonded to each other via a bonding group B, and the hydrogen atoms bonded to them are each independently —COOR 0 (wherein R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group), —NO 2
  • Y 2 is a group selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof,
  • the hydrogen atom bonded to each independently represents —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms.
  • R May be substituted with an alkyloxy group of R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or the same definition as Y 1 ;
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • X may be the same or different;
  • Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and the hydrogen atoms bonded thereto are independently —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH— May be substituted with CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • X is —CH ⁇ CH—CO—O— or —O—CO—CH ⁇ CH—
  • P or Q on the side to which —CH ⁇ CH— is bonded is an aromatic ring
  • l1 is 0 or 1
  • l2 is an integer from 0 to 2
  • A represents a single bond when T is a single bond
  • B represents a single bond when T is a single bond
  • H and I are each independently a group selected from a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, and combinations thereof.
  • the side chain may be any one type of photosensitive side chain selected from the group consisting of the following formulas (7) to (10).
  • the side chain may be any one type of photosensitive side chain selected from the group consisting of the following formulas (11) to (13).
  • A, X, l, m and R have the same definition as above.
  • the side chain may be a photosensitive side chain represented by the following formula (14) or (15).
  • A, Y 1 , X, 1, m1, and m2 have the same definition as above.
  • the side chain may be a photosensitive side chain represented by the following formula (16) or (17).
  • A, X, l and m have the same definition as above.
  • the side chain is preferably a photosensitive side chain represented by the following formula (18) or (19).
  • A, B, Y 1 , q1, q2, m1, and m2 have the same definition as above.
  • R 1 represents a hydrogen atom, —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms. Represents an oxy group.
  • the side chain is preferably a photosensitive side chain represented by the following formula (20).
  • A, Y 1 , X, l and m have the same definition as above.
  • any one liquid crystalline side chain selected from the group consisting of the following formulas (21) to (31) is preferable.
  • A, B, q1 and q2 have the same definition as above;
  • Y 3 is a group selected from the group consisting of a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing heterocycle, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • Each hydrogen atom bonded thereto may be independently substituted with —NO 2 , —CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
  • R 3 is a hydrogen atom, —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, halogen group, monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing Represents a heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; l represents an integer of 1 to 12, m represents an integer of 0 to 2, provided that in the formulas (25) to (26), the sum of all m is 2 or more, and the formulas (27) to (28 ), The sum of all m
  • the photosensitive side chain polymer capable of exhibiting the above liquid crystallinity can be obtained by polymerizing the photoreactive side chain monomer having the above photosensitive side chain and the liquid crystalline side chain monomer.
  • the photoreactive side chain monomer is a monomer capable of forming a polymer having a photosensitive side chain at the side chain portion of the polymer when the polymer is formed.
  • the photoreactive group possessed by the side chain the following structures and derivatives thereof are preferred.
  • photoreactive side chain monomer examples include radical polymerizable groups such as hydrocarbon, (meth) acrylate, itaconate, fumarate, maleate, ⁇ -methylene- ⁇ -butyrolactone, styrene, vinyl, maleimide, norbornene, etc.
  • a polymerizable side group composed of at least one selected from the group consisting of siloxane and a photosensitive side chain consisting of at least one of the above formulas (1) to (6), preferably, for example, the above formula (7 ) To (10), a photosensitive side chain comprising at least one of the above formulas (11) to (13), and a photosensitivity represented by the above formula (14) or (15).
  • a photosensitive side chain a photosensitive side chain represented by the above formula (16) or (17), a photosensitive side chain represented by the above formula (18) or (19), and a photosensitivity represented by the above formula (20).
  • Sex side chain It is preferable that it has a structure.
  • photoreactive side chain monomers examples include monomers selected from the following formulas M1-1 to M1-7 and M1-17 to M1-20.
  • M1 is a hydrogen atom or a methyl group
  • s1 represents the number of methylene groups, and is a natural number of 2 to 9.
  • R is OH or NH 2
  • M1 is a hydrogen atom or a methyl group
  • s1 represents the number of methylene groups is a natural number of 2 to 9.
  • Examples of the monomer having a photoalignable group represented by the above formula (1) include 4- (6-methacryloxyhexyl-1-oxy) cinnamic acid, 4- (6-acryloxyhexyl-1-oxy), and the like.
  • Cinnamic acid, 4- (3-methacryloxypropyl-1-oxy) cinnamic acid, 4- (4- (6-methacryloxyhexyl-1-oxy) benzoyloxy) cinnamic acid, and the like (1 ) In which R is OH, and 4- (6-methacryloxyhexyl-1-oxy) cinnamamide, 4- (6-acryloxyhexyl-1-oxy) cinnamamide, 4- (3-methacryloxypropyl- And those in which R in formula (1) is NH 2 , such as 1-oxy) cinnamamide.
  • the liquid crystalline side chain monomer is a monomer in which a polymer derived from the monomer exhibits liquid crystallinity and the polymer can form a mesogenic group at a side chain site.
  • a mesogenic group having a side chain even if it is a group having a mesogen structure alone such as biphenyl or phenylbenzoate, or a group having a mesogen structure by hydrogen bonding between side chains such as benzoic acid Good.
  • the mesogenic group possessed by the side chain the following structure is preferable.
  • liquid crystalline side chain monomers include hydrocarbon, (meth) acrylate, itaconate, fumarate, maleate, ⁇ -methylene- ⁇ -butyrolactone, styrene, vinyl, maleimide, norbornene and other radical polymerizable groups
  • a structure having a polymerizable group composed of at least one selected from the group consisting of siloxanes and a side chain composed of at least one of the above formulas (21) to (31) is preferable.
  • liquid crystalline monomers as a monomer having a carboxyl group, a monomer represented by a formula selected from the group consisting of the following formulas M2-1 to M2-9 can also be used.
  • R is OH or NH 2
  • M1 is a hydrogen atom or a methyl group
  • s1 represents the number of methylene groups is a natural number of 2 to 9.
  • a monomer having a substituent that exhibits liquid crystallinity which is an example of the other monomer
  • a monomer represented by a formula selected from the group consisting of the following formulas M2-10 to M2-16 can also be used.
  • M1 is a hydrogen atom or a methyl group
  • s1 represents the number of methylene groups, and is a natural number of 2 to 9.
  • the side chain type polymer can be obtained by a copolymerization reaction of the above-described photoreactive side chain monomer exhibiting liquid crystallinity. Further, it can be obtained by copolymerization of a photoreactive side chain monomer that does not exhibit liquid crystallinity and a liquid crystalline side chain monomer, or by copolymerization of a photoreactive side chain monomer that exhibits liquid crystallinity and a liquid crystalline side chain monomer. it can. Furthermore, it can be copolymerized with other monomers as long as the liquid crystallinity is not impaired.
  • Examples of other monomers include industrially available monomers capable of radical polymerization reaction. Specific examples of the other monomer include unsaturated carboxylic acid, acrylic ester compound, methacrylic ester compound, maleimide compound, acrylonitrile, maleic anhydride, styrene compound and vinyl compound.
  • unsaturated carboxylic acid examples include acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid and the like.
  • acrylic ester compound examples include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2,2,2-trifluoroethyl acrylate, tert-butyl.
  • methacrylic acid ester compound examples include methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl.
  • vinyl compound examples include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
  • styrene compound examples include styrene, methyl styrene, chlorostyrene, bromostyrene, and the like.
  • maleimide compounds include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
  • the content of the photoreactive side chain in the side chain polymer of the present invention is preferably 10 mol% to 100 mol%, more preferably 20 mol% to 95 mol%, more preferably 30 mol% from the viewpoint of liquid crystal alignment. More preferred is ⁇ 90 mol%.
  • the content of the liquid crystalline side chain in the side chain polymer of the present invention is preferably 90 mol% or less, more preferably 5 mol% to 80 mol%, more preferably 10 mol% to 70 mol%, from the viewpoint of liquid crystal alignment. Is more preferable.
  • the side chain type polymer of the present invention may contain other side chains other than the photoreactive side chain and the liquid crystalline side chain.
  • the content is the remaining portion when the total content of the photoreactive side chain and the liquid crystalline side chain is less than 100%.
  • the production method of the side chain polymer of the present embodiment is not particularly limited, and a general-purpose method that is handled industrially can be used. Specifically, it can be produced by cationic polymerization, radical polymerization, or anionic polymerization using a vinyl group of a liquid crystalline side chain monomer or photoreactive side chain monomer. Among these, radical polymerization is particularly preferable from the viewpoint of ease of reaction control.
  • RAFT reversible addition-cleavage chain transfer
  • a radical thermal polymerization initiator is a compound that generates radicals when heated to a decomposition temperature or higher.
  • radical thermal polymerization initiators include ketone peroxides (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.), diacyl peroxides (acetyl peroxide, benzoyl peroxide, etc.), hydroperoxides (peroxidation).
  • the radical photopolymerization initiator is not particularly limited as long as it is a compound that initiates radical polymerization by light irradiation.
  • examples of such radical photopolymerization initiators include benzophenone, Michler's ketone, 4,4′-bis (diethylamino) benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, 2-hydroxy -2-methylpropiophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, isopropyl benzoin ether, isobutyl benzoin ether, 2,2-diethoxyacetophenone, 2,2 -Dimethoxy-2-phenylacetophenone, camphorquinone, benzanthrone, 2-methyl-1- [4- (
  • the radical polymerization method is not particularly limited, and an emulsion polymerization method, suspension polymerization method, dispersion polymerization method, precipitation polymerization method, bulk polymerization method, solution polymerization method and the like can be used.
  • the organic solvent used for the polymerization reaction of the photosensitive side chain polymer capable of exhibiting liquid crystallinity is not particularly limited as long as the generated polymer is soluble. Specific examples are given below.
  • organic solvents may be used alone or in combination. Furthermore, even if it is a solvent which does not dissolve the polymer
  • the polymerization temperature at the time of radical polymerization can be selected from any temperature of 30 ° C. to 150 ° C., but is preferably in the range of 50 ° C. to 100 ° C.
  • the reaction can be carried out at any concentration, but if the concentration is too low, it is difficult to obtain a high molecular weight polymer, and if the concentration is too high, the viscosity of the reaction solution becomes too high and uniform stirring is difficult. Therefore, the monomer concentration is preferably 1% by mass to 50% by mass, more preferably 5% by mass to 30% by mass.
  • the initial stage of the reaction is carried out at a high concentration, and then an organic solvent can be added.
  • the molecular weight of the obtained polymer is decreased when the ratio of the radical polymerization initiator is large relative to the monomer, and the molecular weight of the obtained polymer is increased when the ratio is small, the ratio of the radical initiator is
  • the content is preferably 0.1 mol% to 10 mol% with respect to the monomer to be polymerized. Further, various monomer components, solvents, initiators and the like can be added during the polymerization.
  • the polymer deposited in a poor solvent and precipitated can be recovered by filtration and then dried at normal temperature or under reduced pressure at room temperature or by heating.
  • impurities in the polymer can be reduced.
  • the poor solvent at this time include alcohols, ketones, hydrocarbons and the like, and it is preferable to use three or more kinds of poor solvents selected from these because purification efficiency is further improved.
  • the molecular weight of the (A) side chain polymer of the present invention is measured by a GPC (Gel Permeation Chromatography) method in consideration of the strength of the obtained coating film, workability at the time of forming the coating film, and uniformity of the coating film.
  • the weight average molecular weight is preferably 2,000 to 1,000,000, more preferably 5,000 to 100,000.
  • a dichroic dye refers to a dye having the property that the absorbance in the major axis direction of a molecule is different from the absorbance in the minor axis direction.
  • the dichroic dye preferably has an absorption maximum wavelength ( ⁇ MAX) in the range of 300 to 700 nm.
  • dichroic dyes include acridine dyes, oxazine dyes, cyanine dyes, naphthalene dyes, azo dyes and anthraquinone dyes, and among them, azo dyes are preferable.
  • azo dyes include monoazo dyes, bisazo dyes, trisazo dyes, tetrakisazo dyes, and stilbene azo dyes, and bisazo dyes and trisazo dyes are preferable.
  • Examples of the azo dye include a compound represented by the formula (b) (hereinafter sometimes referred to as “compound (b)”).
  • a 1 (-N NA 2 )
  • a 2 represents a 1,4-phenylene group which may have a substituent, a naphthalene-1,4-diyl group which may have a substituent, or a divalent which may have a substituent. Represents a heterocyclic group.
  • p represents an integer of 1 to 4. When p is an integer of 2 or more, the plurality of A 2 may be the same or different independently of each other. ]
  • Examples of the monovalent heterocyclic group include groups in which one hydrogen atom has been removed from a heterocyclic compound such as quinoline, thiazole, benzothiazole, thienothiazole, imidazole, benzimidazole, oxazole and benzoxazole.
  • Examples of the divalent heterocyclic group include groups in which two hydrogen atoms have been removed from the heterocyclic compound.
  • the phenyl group, naphthyl group and monovalent heterocyclic group in A 1 and A 3 and the p-phenylene group, naphthalene-1,4-diyl group and divalent heterocyclic group in A 2 optionally have Is an alkyl group having 1 to 4 carbon atoms; an alkoxy group having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group and a butoxy group; a fluorinated alkyl group having 1 to 4 carbon atoms such as a trifluoromethyl group; a cyano group; Nitro group; halogen atom; substituted or unsubstituted amino group such as amino group, diethylamino group and pyrrolidino group (substituted amino group is an amino group having one or two alkyl groups having 1 to 6 carbon atoms, or two This means an amino group in which substituted alkyl groups are bonded to each other to form an alkanediy
  • the alkyl group having 1 to 6 carbon atoms may be linear or branched, and is a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, or s-butyl group.
  • Examples include a pentyl group, 2-methylpentyl group, 1,1-dimethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylpropyl group, and the like.
  • B 1 to B 20 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, a nitro group, a substituted or unsubstituted amino group (a substituted amino group and As defined above, the unsubstituted amino group represents a chlorine atom or a trifluoromethyl group.
  • n1 to n4 each independently represents an integer of 0 to 3.
  • the plurality of B 2 when n1 is 2 or more, the plurality of B 2 may be the same or different independently of each other; when n2 is 2 or more, the plurality of B 6 may be the same or different independently of each other; when n3 is 2 or more, the plurality of B 9 may be the same or different independently of each other; When n4 is 2 or more, the plurality of B 14 may be the same or different independently of each other.
  • the anthraquinone dye is preferably a compound represented by the formula (2-7).
  • R 1 to R 8 each independently represent a hydrogen atom, —R x , —NH 2 , —NHR x , —NR x 2 , —SR x, or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • the oxazone dye is preferably a compound represented by the formula (2-8).
  • R 9 to R 15 each independently represent a hydrogen atom, —R x , —NH 2 , —NHR x , —NR x 2 , —SR x, or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • the acridine dye is preferably a compound represented by the formula (2-9).
  • R 16 to R 23 each independently represent a hydrogen atom, —R x , —NH 2 , —NHR x , —NR x 2 , —SR x, or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • examples of the alkyl group having 1 to 4 carbon atoms represented by R x include a methyl group, an ethyl group, a propyl group, and a butyl group. A pentyl group, a hexyl group, and the like.
  • examples of the aryl group having 6 to 12 carbon atoms include a phenyl group, a toluyl group, a xylyl group, and a naphthyl group.
  • the cyanine dye is preferably a compound represented by the formula (2-10) and a compound represented by the formula (2-11).
  • D 1 and D 2 each independently represent a group represented by any one of formulas (2-10a) to (2-10d).
  • n5 represents an integer of 1 to 3.
  • D 3 and D 4 each independently represent a group represented by any one of formulas (2-11a) to (2-11h).
  • n6 represents an integer of 1 to 3.
  • dichroic dyes examples include G-207, G-241, G-470 (manufactured by Hayashibara), Yellow-8, KRD-901, KRD-902 (Showa Chemical Industry). And SI-486 (Mitsui Chemicals).
  • the content of the dichroic dye as the component (B) in the polarizing layer forming composition is 100 parts by mass of the side chain polymer as the component (A) from the viewpoint of improving the orientation of the dichroic dye.
  • it is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less, further preferably 0.1 parts by mass or more and 10 parts by mass or less, and more preferably 0.1 parts by mass or more. 5 parts by mass or less is particularly preferable.
  • the polymer composition of this invention can also contain the compound represented by a following formula (c) as (C) component.
  • formula (c) any three to five of R 101 , R 102 , R 103 , R 104 and R 105 are each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, C 1 -C 6.
  • One or more hydrogen atoms in the carbocycle or heterocycle may be replaced with a fluorine atom or an organic group, and —CH 2 CH 2 — in R 106 is replaced with —CH ⁇ CH—.
  • R 106 may be replaced by phenylene or a divalent carbocyclic or heterocyclic ring, and when any of the following groups is not adjacent to each other: These groups may be substituted: —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, —CO—, wherein R 107 is a hydrogen atom or methyl Base .), And n represents 0 or 1.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • C a -C b alkyl in the present specification represents a linear or branched hydrocarbon group comprising a to b carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 1,1-dimethylbutyl group, Specific examples include 1,3-dimethylbutyl group, heptyl group, octyl group, nonyl group, decyl group, undec
  • C a -C b haloalkyl in this specification is a linear or branched chain consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • fluoromethyl group chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, chlorofluoromethyl group, dichloromethyl group, bromofluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, dichlorofluoromethyl group, trichloromethyl Group, bromodifluoromethyl group, bromochlorofluoromethyl group, dibromofluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl Group, 2,2-dichloroethyl group, 2-bromo-2-fluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2-dichloro-2 -Fl group, 2-chloro-2,2-
  • C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms.
  • cyclopropyl group 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, 2,2,3,3-tetramethylcyclopropyl group, cyclobutyl group, cyclopentyl group, 2- Specific examples include methylcyclopentyl group, 3-methylcyclopentyl group, cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, bicyclo [2.2.1] heptan-2-yl group and the like. , Each selected range of carbon atoms.
  • C a -C b halocycloalkyl represents a cyclic hydrocarbon group having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And can form monocyclic or complex ring structures from 3 to 6-membered rings.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, 2- (trifluoromethyl) cyclohexyl group, 3- (trifluoromethyl) cyclohexyl group , 4- (trifluoromethyl) cyclohexyl group and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule.
  • Represents a saturated hydrocarbon group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 2 -Pentenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 2-ethyl-2-propenyl group, 1,1-dimethyl-2-propenyl group, 2-hexenyl group, 2-methyl Specific examples include 2-pentenyl group, 2,4-dimethyl-2,6-heptadienyl group, 3,7-dimethyl-2,6-octadienyl group, etc. Is done.
  • C a -C b haloalkenyl is a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more double bonds in the molecule.
  • the halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms.
  • a monocyclic or complex ring structure from a member ring to a 6-member ring can be formed.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-.
  • 2-cyclopenten-1-yl group, 3-cyclopenten-1-yl group, 2-cyclohexen-1-yl group, 3-cyclohexen-1-yl group, bicyclo [2.2.1] -5-hepten-2- Specific examples include yl groups and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b halocycloalkenyl in the present specification is a cyclic one having 1 to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • it represents an unsaturated hydrocarbon group having two or more double bonds, and can form a monocyclic or complex ring structure having 3 to 6 members.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-.
  • substitution by a halogen atom may be a ring structure part, a side chain part or both of them, and when substituted by two or more halogen atoms, those halogen atoms May be the same as or different from each other.
  • a 2-chlorobicyclo [2.2.1] -5-hepten-2-yl group and the like are given as specific examples, and each group is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynyl is a linear or branched chain composed of a to b carbon atoms and has one or more triple bonds in the molecule.
  • Represents a hydrocarbon group for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 1-methyl-2-propynyl group, 2-pentynyl group, 1-methyl-2-butynyl group, 1,
  • Specific examples include a 1-dimethyl-2-propynyl group, a 2-hexynyl group, and the like, and each is selected within the specified number of carbon atoms.
  • C a -C b haloalkynyl represents a linear or branched chain comprising a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more triple bonds in the molecule.
  • the halogen atoms may be the same as or different from each other.
  • Specific examples include 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the like. Each of which is selected for each specified number of carbon atoms.
  • C a -C b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methoxy group, ethoxy group, n-propyloxy group, Specific examples include i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group, n-pentyloxy group, n-hexyloxy group, etc. It is selected in the range of the number of atoms.
  • C a -C b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 , 1,2-trifluoroethoxy group, 2-bromo-1,1,2-trifluoroethoxy group, pentafluoroethoxy group, 2,2-dichloro-1,1,2-trifluoroethoxy group, 2,2 , 2-trichloro-1,1-difluoroethoxy group, 2-bromo-1,1,2,2-tetrafluoroeth
  • (C a -C b alkyl) carbonyl in the present specification represents an alkyl-C (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as an acetyl group, a propionyl group, Specific examples include butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like, and each is selected in the range of the designated number of carbon atoms.
  • the notation of (C a -C b haloalkyl) carbonyl in the present specification represents a haloalkyl-C (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as fluoroacetyl group, chloroacetyl Group, difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylprop
  • Specific examples include a noyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • (C a -C b alkoxy) carbonyl in the present specification represents an alkyl-OC (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl Specific examples include a group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, etc. Selected.
  • the expression (C a -C b haloalkoxy) carbonyl represents a haloalkyl-OC (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as 2-chloroethoxycarbonyl.
  • Group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, etc., are given as specific examples, and each designated range of the number of carbon atoms. Selected.
  • the notation of (C a -C b alkylamino) carbonyl in the present specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above meaning consisting of a to b carbon atoms, for example, Specific examples include methylcarbamoyl group, ethylcarbamoyl group, n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group, i-butylcarbamoyl group, s-butylcarbamoyl group, t-butylcarbamoyl group and the like. , Each selected range of carbon atoms.
  • the expression (C a -C b haloalkylamino) carbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with a haloalkyl group having the above meaning consisting of a to b carbon atoms, for example 2
  • Specific examples include -fluoroethylcarbamoyl group, 2-chloroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2,2,2-trifluoroethylcarbamoyl group, etc. Selected.
  • di (C a -C b alkyl) aminocarbonyl means in the above meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b.
  • Represents a carbamoyl group substituted by an alkyl group for example, N, N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-di-n-propylcarbamoyl group Specific examples include N, N-di-n-butylcarbamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • the substituents R 101 , R 102 , R 103 , R 104, and R 105 in the cinnamic acid or benzoic acid derivative having the structure represented by the formula (2) are each independently a hydrogen atom, a halogen atom, C 1- A substituent selected from C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, cyano and nitro is preferred.
  • R 13 is preferably a substituent other than a hydrogen atom in the definitions of R 101 , R 102 , R 103 , R 104 and R 105 described above, from the viewpoint of orientation sensitivity, and preferably a halogen atom, C 1 More preferred are substituents selected from -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, cyano and nitro.
  • R 101, R 102, R 103 , R 104 and R 105 is a group represented by the formula (3), among others, R 103 has the formula ( The group represented by 3) is preferable.
  • R 103 has the formula ( The group represented by 3) is preferable.
  • monomers include monomers selected from the formulas M1-1 to M1-7 and M1-17 to M1-21 as monomers having a cinnamic acid group.
  • monomer having a benzoic acid group include monomers selected from the formulas M2-1 to M2-9.
  • Examples of such cinnamic acid and derivatives thereof include cinnamic acid, 4-methoxycinnamic acid, 4-ethoxy cinnamic acid, 4-propoxy cinnamic acid, 4-fluoro cinnamic acid, and the like.
  • monomers having a cinnamic acid group such as 4- (4- (6- (6-methacryloxyhexyl-1-oxy) benzoyloxy) cinnamic acid.
  • benzoic acid and derivatives thereof include benzoic acid derivatives such as benzoic acid, 4-methoxybenzoic acid, 4-ethoxybenzoic acid, 4-propoxybenzoic acid, 4-fluorobenzoic acid; 4- (6- Methacryloxyhexyl-1-oxy) benzoic acid, 4- (6-acryloxyhexyl-1-oxy) benzoic acid, 4- (3-methacryloxypropyl-1-oxy) benzoic acid, 4- (4- (6 And monomers having a benzoic acid group such as methacryloxyhexyl-1-oxy) benzoyloxy) benzoic acid.
  • benzoic acid derivatives such as benzoic acid, 4-methoxybenzoic acid, 4-ethoxybenzoic acid, 4-propoxybenzoic acid, 4-fluorobenzoic acid
  • 4- (6- Methacryloxyhexyl-1-oxy) benzoic acid 4- (6-acryloxyhexyl-1-oxy) benzoic acid, 4- (3-methacryloxypropyl-1-oxy)
  • the content when the component (C) is contained, the content is preferably 3 parts by mass to 100 parts by mass per 100 parts by mass of the resin of the component (A).
  • the content of the component (C) is 3 parts by mass or less, the irradiation margin is not improved.
  • the solvent tolerance of the cured film obtained may fall that content of (C) component exceeds 100 mass parts and is excessive.
  • the organic solvent used for the polymer composition used in the present invention is not particularly limited as long as it is an organic solvent that dissolves the resin component. Specific examples are given below. N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 2-pyrrolidone, N-ethylpyrrolidone, N-vinylpyrrolidone, dimethylsulfoxide, tetramethylurea, pyridine, Dimethylsulfone, hexamethylsulfoxide, ⁇ -butyrolactone, 3-methoxy-N, N-dimethylpropanamide, 3-ethoxy-N, N-dimethylpropanamide, 3-butoxy-N, N-dimethylpropanamide, 1,3 -Dimethyl-imidazolidinone, ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone,
  • the polymer composition of the present invention contains (A) a photosensitive side chain polymer that exhibits liquid crystallinity in a predetermined temperature range, (B) a dichroic dye, and an organic solvent. Moreover, the compound represented by the said Formula (c) is contained as needed.
  • the polymer composition used in the present invention is preferably prepared as a coating solution so as to be suitable for forming a polarizing layer. That is, the polymer composition used in the present invention is preferably prepared as a solution in which a resin component for forming a resin film is dissolved in an organic solvent.
  • the resin component is a resin component containing a photosensitive side chain polymer capable of exhibiting the liquid crystallinity already described.
  • the content of the resin component is preferably 1% by mass to 20% by mass, more preferably 3% by mass to 15% by mass, and particularly preferably 3% by mass to 10% by mass.
  • the resin component described above may be a photosensitive side chain polymer that can all exhibit the above-described liquid crystallinity, but does not impair the liquid crystal developing ability and the photosensitive performance.
  • Other polymers may be mixed within the range.
  • the content of the other polymer in the resin component is 0.5 to 80% by mass, preferably 1 to 50% by mass.
  • examples of such other polymers include polymers that are made of poly (meth) acrylate, polyamic acid, polyimide, and the like and are not a photosensitive side chain polymer that can exhibit liquid crystallinity.
  • the polymer composition used in the present invention may contain components other than the above (A), (B) and organic solvent.
  • examples thereof include compounds that improve the film thickness uniformity and surface smoothness when the polymer composition is applied, compounds that improve the adhesion between the polarizing layer and the substrate, and the like. It is not limited.
  • Examples of the compound that improves film thickness uniformity and surface smoothness include fluorine-based surfactants, silicone-based surfactants, and nonionic surfactants. More specifically, for example, Ftop (registered trademark) 301, EF303, EF352 (manufactured by Tochem Products), MegaFac (registered trademark) F171, F173, R-30 (manufactured by DIC), Florard FC430, FC431 (Manufactured by Sumitomo 3M), Asahi Guard (registered trademark) AG710 (manufactured by Asahi Glass Company), Surflon (registered trademark) S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Seimi Chemical Co., Ltd.) It is done.
  • the use ratio of these surfactants is preferably 0.01 to 2 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the resin component contained in the polymer
  • the compound that improves the adhesion between the polarizing layer and the substrate include the following functional silane-containing compounds.
  • the following phenoplast type or epoxy group-containing compound additives may be included in the polymer composition for the purpose of imparting heat resistance.
  • Specific phenoplast additives are shown below, but are not limited to this structure.
  • Specific epoxy group-containing compounds include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5,6-tetraglycidyl-2,4-hexanediol, N, N, N ′, N ′,-tetraglycidyl-m-xylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N, N ′, N ′,-tetraglycidyl- , 4'-diaminodip
  • the amount used is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the resin component contained in the polymer composition. More preferably, it is 1 to 20 parts by mass. If the amount used is less than 0.1 parts by mass, the effect of improving the adhesion cannot be expected, and if it exceeds 30 parts by mass, the orientation of the liquid crystal may deteriorate.
  • a photosensitizer can also be used as an additive. Colorless and triplet sensitizers are preferred.
  • photosensitizers aromatic nitro compounds, coumarins (7-diethylamino-4-methylcoumarin, 7-hydroxy4-methylcoumarin), ketocoumarins, carbonyl biscoumarins, aromatic 2-hydroxyketones, and amino-substituted Aromatic 2-hydroxyketones (2-hydroxybenzophenone, mono- or di-p- (dimethylamino) -2-hydroxybenzophenone), acetophenone, anthraquinone, xanthone, thioxanthone, benzanthrone, thiazoline (2-benzoylmethylene-3 -Methyl- ⁇ -naphthothiazoline, 2- ( ⁇ -naphthoylmethylene) -3-methylbenzothiazoline, 2- ( ⁇ -naphthoylmethylene) -3-methylbenzothiazoline, 2- (4-b
  • Aromatic 2-hydroxy ketone (benzophenone), coumarin, ketocoumarin, carbonyl biscoumarin, acetophenone, anthraquinone, xanthone, thioxanthone, and acetophenone ketal are preferred.
  • a method for producing a substrate having a polarizing layer of the present invention is as follows. [I] (A) A polymer composition containing a photosensitive side chain polymer exhibiting liquid crystallinity in a predetermined temperature range, (B) a dichroic dye and an organic solvent is applied onto a substrate. Forming a coating film; [II] a step of irradiating the coating film obtained in [I] with polarized ultraviolet rays; and [III] a step of heating the coating film obtained in [II]; Have Through the above-described steps, a polarizing layer imparted with polarizing performance can be obtained, and a substrate having the polarizing layer can be obtained.
  • step [I] a polymer composition containing (A) a photosensitive side chain polymer that exhibits liquid crystallinity in a predetermined temperature range, (B) a dichroic dye, and an organic solvent on a substrate. Apply to form a coating film.
  • the substrate is usually a transparent substrate.
  • a transparent substrate When the substrate of the polarizing plate of the present invention (hereinafter sometimes referred to as the present polarizing plate) is not installed on the display surface of the display element, for example, a polarizing film obtained by removing the substrate from the polarizing plate is used as the display surface of the display element. In the case of installation, the substrate may not be transparent.
  • the transparent substrate means a substrate having transparency capable of transmitting light, particularly visible light, and the transparency means a characteristic that a transmittance with respect to a light beam having a wavelength of 380 to 780 nm is 80% or more. Specific examples of the transparent substrate include a translucent resin substrate.
  • polyolefin such as polyethylene and polypropylene
  • cyclic olefin resin such as norbornene polymer
  • polyvinyl alcohol polyethylene terephthalate
  • polymethacrylate ester polyacrylate ester
  • triacetylcellulose diacetyl Cellulose esters such as cellulose and cellulose acetate propionate
  • polyethylene naphthalate polycarbonate
  • polysulfone polyethersulfone
  • polyetherketone polyphenylene sulfide and polyphenylene oxide
  • polyethylene terephthalate, polymethacrylic acid ester, cellulose ester, cyclic olefin resin or polycarbonate is preferred.
  • Cellulose ester is obtained by esterifying a part or all of hydroxyl groups contained in cellulose and can be easily obtained from the market. Cellulose ester base materials can also be easily obtained from the market. Examples of commercially available cellulose ester substrates include “Fujitac Film” (Fuji Photo Film Co., Ltd.); “KC8UX2M”, “KC8UY” and “KC4UY” (Konica Minolta Opto Co., Ltd.).
  • Cyclic olefin resin is easily available from the market.
  • Commercially available cyclic olefin resins include “Topas” [Ticona (Germany)], “Arton” [JSR Corporation], “ZEONOR” [Nippon Zeon Corporation], and “ZEONEX”. [Nippon Zeon Co., Ltd.] and “Apel” [Mitsui Chemicals Co., Ltd.].
  • Such a cyclic olefin resin can be formed into a substrate by, for example, forming a film by a known means such as a solvent casting method or a melt extrusion method.
  • a commercially available cyclic olefin resin substrate can also be used.
  • cyclic olefin resin base materials include “Essina” [Sekisui Chemical Co., Ltd.], “SCA40” [Sekisui Chemical Co., Ltd.], “Zeonor Film” [Optes Co., Ltd.], and “Arton Film”. [JSR Corporation].
  • the cyclic olefin-based resin is a copolymer of a cyclic olefin and an aromatic compound having a chain olefin or a vinyl group
  • the content ratio of the structural unit derived from the cyclic olefin is the total structural unit of the copolymer. On the other hand, it is usually 50 mol% or less, preferably in the range of 15 to 50 mol%.
  • chain olefins include ethylene and propylene
  • examples of aromatic compounds having a vinyl group include styrene, ⁇ -methylstyrene, and alkyl-substituted styrene.
  • the cyclic olefin-based resin is a ternary copolymer of a cyclic olefin, a chain olefin, and an aromatic compound having a vinyl group
  • the content ratio of the structural unit derived from the chain olefin is that of the copolymer.
  • the content of the structural unit derived from the aromatic compound having a vinyl group is usually 5 to 80 mol% based on the total structural unit, and the content of the structural unit derived from the aromatic compound having a vinyl group is usually 5 to 80 mol% based on the total structural unit of the copolymer. It is.
  • Such a terpolymer has the advantage that the amount of expensive cyclic olefin used can be relatively reduced in its production.
  • the characteristics required for the substrate vary depending on the configuration of the polarizing plate, but usually a substrate having as small a retardation as possible is preferable.
  • the substrate having as little retardation as possible include cellulose ester films having no phase difference, such as zero tack (Konica Minolta Opto Co., Ltd.), Z tack (Fuji Film Co., Ltd.), and the like.
  • an unstretched cyclic olefin resin substrate is also preferable.
  • the surface of the substrate on which the polarizing layer is not formed may be subjected to a hard coat treatment, an antireflection treatment, an antistatic treatment, or the like.
  • the hard coat layer may contain additives such as an ultraviolet absorber as long as the performance is not affected.
  • the thickness of the substrate is usually 5 to 300 ⁇ m, preferably 20 to 200 ⁇ m, because if the substrate is too thin, the strength tends to decrease and the workability tends to be inferior.
  • the method for applying the polymer composition described above on the substrate is not particularly limited.
  • the application method is generally performed by screen printing, offset printing, flexographic printing, an inkjet method, or the like.
  • Other coating methods include a dipping method, a roll coater method, a slit coater method, a spinner method (rotary coating method), or a spray method, and these may be used depending on the purpose.
  • the polymer composition After the polymer composition is applied on the substrate, it is heated at 50 to 230 ° C., preferably at 50 to 200 ° C. for 0.4 minutes to 60 minutes by a heating means such as a hot plate, a thermal circulation oven or an IR (infrared) oven.
  • the coating film can be obtained by evaporating the solvent for a period of time, preferably 0.5 minutes to 10 minutes.
  • the drying temperature at this time is preferably lower than the liquid crystal phase expression temperature of the side chain polymer.
  • the thickness of the coating film is usually 10 ⁇ m or less. Preferably they are 0.5 micrometer or more and 9.5 micrometers or less, and 0.8 micrometer or more and 5 micrometers or less are more preferable.
  • the thickness can be usually determined by measurement with an interference film thickness meter, a laser microscope or a stylus thickness meter.
  • step [II] the coating film obtained in step [I] is irradiated with polarized ultraviolet rays.
  • the substrate is irradiated with polarized ultraviolet rays through a polarizing plate from a certain direction.
  • ultraviolet rays to be used ultraviolet rays having a wavelength in the range of 100 nm to 400 nm can be used.
  • the optimum wavelength is selected through a filter or the like depending on the type of coating film to be used.
  • ultraviolet light having a wavelength in the range of 290 nm to 400 nm can be selected and used so that the photocrosslinking reaction can be selectively induced.
  • the ultraviolet light for example, light emitted from a high-pressure mercury lamp can be used.
  • the irradiation amount of polarized ultraviolet rays depends on the coating film used.
  • the amount of irradiation is polarized ultraviolet light that realizes the maximum value of ⁇ A (hereinafter also referred to as ⁇ Amax), which is the difference between the ultraviolet light absorbance in a direction parallel to the polarization direction of polarized ultraviolet light and the ultraviolet light absorbance in a direction perpendicular to the polarization direction of the polarized ultraviolet light.
  • the amount is preferably in the range of 1% to 70%, more preferably in the range of 1% to 50%.
  • step [III] the ultraviolet-irradiated coating film polarized in step [II] is heated.
  • the polarizing performance can be imparted to the coating film by heating.
  • a heating means such as a hot plate, a heat circulation type oven, or an IR (infrared) type oven can be used.
  • the heating temperature can be determined in consideration of the temperature at which the liquid crystallinity of the coating film used is developed.
  • the heating temperature is preferably within the temperature range of the temperature at which the side chain polymer exhibits liquid crystallinity (hereinafter referred to as liquid crystal expression temperature).
  • the liquid crystal expression temperature on the coating film surface is expected to be lower than the liquid crystal expression temperature when a photosensitive side chain polymer that can exhibit liquid crystallinity is observed in bulk.
  • the heating temperature is more preferably within the temperature range of the liquid crystal expression temperature on the coating film surface. That is, the temperature range of the heating temperature after irradiation with polarized ultraviolet rays is 10 ° C. lower than the lower limit of the temperature range of the liquid crystal expression temperature of the side chain polymer used, and 10 ° C.
  • the liquid crystal expression temperature is not less than the glass transition temperature (Tg) at which the side chain polymer or coating film surface undergoes a phase transition from the solid phase to the liquid crystal phase, and from the liquid crystal phase to the isotropic phase (isotropic phase). It means a temperature below the isotropic phase transition temperature (Tiso) that causes a phase transition.
  • the thickness of the coating film formed after heating is preferably 0.5 ⁇ m or more and 9.5 ⁇ m or less, and more preferably 0.8 ⁇ m or more and 5 ⁇ m or less for the same reason described in the step [I].
  • the production method of the present invention can realize highly efficient introduction of anisotropy into the coating film.
  • polarized-light performance with high efficiency can be manufactured.
  • substrate with a coating film of this invention irradiates the polarized ultraviolet-ray, after apply
  • the coating film used in the present invention realizes the introduction of highly efficient anisotropy into the coating film by utilizing the principle of molecular reorientation induced by the side chain photoreaction and liquid crystallinity. .
  • polarized ultraviolet rays are formed. After irradiation and then heating, a polarizing element is prepared.
  • the coating film used in the method of the present invention should be a polarizing layer that is highly efficient in anisotropy and has excellent polarization performance by sequentially irradiating the coating film with polarized ultraviolet rays and heat treatment. Can do.
  • the irradiation amount of polarized ultraviolet rays to the coating film and the heating temperature in the heat treatment are optimized. Thereby, introduction of anisotropy into the coating film with high efficiency can be realized.
  • the optimum irradiation amount of polarized ultraviolet rays for introducing highly efficient anisotropy into the coating film used in the present invention is such that the photosensitive group undergoes photocrosslinking reaction, photoisomerization reaction, or photofries rearrangement reaction in the coating film.
  • the photo-crosslinking reaction, photoisomerization reaction, or photo-fleece rearrangement reaction has few photosensitive groups in the side chain, the amount of photoreaction will not be sufficient. . In that case, sufficient self-organization does not proceed even after heating.
  • the crosslinking reaction between the side chains is caused when the photosensitive group of the side chain undergoing the crosslinking reaction becomes excessive. Too much progress. In that case, the resulting film may become rigid and hinder the progress of self-assembly by subsequent heating.
  • the coating film used in the present invention is irradiated with polarized ultraviolet rays to the structure having the light Fleece rearrangement group, if the photosensitive group of the side chain that undergoes the light Fleece rearrangement reaction becomes excessive, the liquid crystallinity of the coating film Will drop too much.
  • the liquid crystallinity of the obtained film is also lowered, which may hinder the progress of self-assembly by subsequent heating. Furthermore, when irradiating polarized ultraviolet light to a structure having a photo-fleece rearrangement group, if the amount of ultraviolet light irradiation is too large, the side-chain polymer is photodegraded, preventing the subsequent self-organization by heating. It may become.
  • the optimum amount of the photopolymerization reaction, photoisomerization reaction, or photofleece rearrangement reaction of the side chain photosensitive group by irradiation with polarized ultraviolet rays is the side chain polymer film. It is preferably 0.1 to 40 mol%, more preferably 0.1 to 20 mol% of the photosensitive group possessed by.
  • the coating film used in the method of the present invention by optimizing the irradiation amount of polarized ultraviolet rays, photocrosslinking reaction or photoisomerization reaction of photosensitive groups or photofleece rearrangement reaction in the side chain of the side chain polymer film Optimize the amount of. Then, in combination with the subsequent heat treatment, highly efficient introduction of anisotropy into the coating film used in the present invention is realized. In that case, a suitable amount of polarized ultraviolet rays can be determined based on the evaluation of ultraviolet absorption of the coating film used in the present invention.
  • the ultraviolet absorption in the direction parallel to the polarization direction of the polarized ultraviolet ray and the ultraviolet absorption in the vertical direction after the irradiation with the polarized ultraviolet ray are measured.
  • ⁇ A which is the difference between the ultraviolet absorbance in the direction parallel to the polarization direction of polarized ultraviolet rays and the ultraviolet absorbance in the direction perpendicular to the polarization direction of the polarized ultraviolet rays.
  • ⁇ Amax the maximum value of ⁇ A ( ⁇ Amax) realized in the coating film used in the present invention and the irradiation amount of polarized ultraviolet light that realizes it are obtained.
  • the amount of irradiation of polarized ultraviolet rays onto the coating film used in the present invention is preferably in the range of 1% to 70% of the amount of polarized ultraviolet rays that realizes ⁇ Amax. More preferably, it is within the range of 50%.
  • the irradiation amount of polarized ultraviolet light within the range of 1% to 50% of the amount of polarized ultraviolet light that realizes ⁇ Amax is 0. 0% of the entire photosensitive group of the side chain polymer film. 1 mol% to 20 mol% corresponds to the amount of polarized ultraviolet light that undergoes a photocrosslinking reaction.
  • a suitable heating temperature as described above is set based on the liquid crystal temperature range of the side chain polymer. It is good to decide. Therefore, for example, when the liquid crystal temperature range of the side chain polymer used in the present invention is 60 ° C. to 200 ° C., the heating temperature after irradiation with polarized ultraviolet light is desirably 50 ° C. to 190 ° C. By doing so, greater anisotropy is imparted to the coating film used in the present invention.
  • the polarizing element provided by the present invention exhibits high reliability against external stresses such as light and heat.
  • the thickness of the polarizing layer is 10 ⁇ m or less, and more preferably 1 ⁇ m or more and 9 ⁇ m or less.
  • the thickness of the alignment layer and the polarizing layer can be usually determined by measurement with an interference film thickness meter, a laser microscope or a stylus thickness meter.
  • the obtained polarizing element can be widely applied to various display elements that require polarized light by using a known method, for example, an antireflection film such as a liquid crystal display element or an organic EL. (Circularly polarizing plate), optical switches, optical filters, and various optical measuring instruments having them as constituent elements.
  • an antireflection film such as a liquid crystal display element or an organic EL. (Circularly polarizing plate), optical switches, optical filters, and various optical measuring instruments having them as constituent elements.
  • Each resin composition of Examples and Comparative Examples contained a solvent, and 1,4-dioxane (DO) and methyl isobutyl ketone (MIBK) were used as the solvent.
  • DO 1,4-dioxane
  • MIBK methyl isobutyl ketone
  • the molecular weight of the acrylic copolymer in the polymerization example was as follows using a room temperature gel permeation chromatography (GPC) apparatus (GPC-101) manufactured by Shodex Co., Ltd. and columns (KD-803, KD-805) manufactured by Shodex Co. And measured.
  • the following number average molecular weight (hereinafter referred to as Mn) and weight average molecular weight (hereinafter referred to as Mw) were expressed in terms of polystyrene.
  • the acrylic copolymer solution was obtained by making it react for time.
  • the acrylic copolymer solution was gradually added dropwise to 1000.0 g of diethyl ether to precipitate a solid, and the residual monomer was removed by filtration and drying under reduced pressure to obtain an acrylic polymer (P2).
  • Mn of the obtained acrylic copolymer was 9,300 and Mw was 16,000.
  • Examples 1 and 2 Each polarizing layer forming composition of Examples 1-2 was prepared with the composition shown in Table 1. About each polarizing element obtained using each polarizing layer formation composition, the polarization degree measurement and the dichroic ratio measurement were performed.
  • Example 1 [Formation of polarizing layer] A polarizing layer forming composition shown in Table 1 was spin-coated on a quartz substrate, dried on a hot plate at 55 ° C. for 60 seconds, and then a coating film having a thickness of 1200 nm was formed. Subsequently, 313 nm linearly polarized light was irradiated perpendicularly
  • the polarization degree of the obtained polarizing element was measured as follows.
  • the transmittance (T1) in the transmission axis direction and the transmittance (T2) in the absorption axis direction were measured using an apparatus in which a folder with a polarizer was set in a spectrophotometer (UV-3600, manufactured by Shimadzu Corporation).
  • the degree of polarization was calculated from the measured transmission axis direction transmittance (T1) and absorption axis direction transmittance (T2) using the following equation.
  • the measurement results are shown in Table 2.
  • Polarization degree (%) ⁇ (T1 ⁇ T2) / (T1 + T2) ⁇ 1/2 ⁇ 100
  • the dichroic ratio of the obtained polarizing element was measured as follows.
  • the absorbance in the direction of the transmission axis (A1) and the absorbance in the direction of the absorption axis (A2) were measured using an apparatus in which a folder with a polarizer was set in a spectrophotometer (Shimadzu Corporation UV-3600).
  • the dichroic ratio was calculated from the measured absorbance (A1) in the transmission axis direction and absorbance (A2) in the absorption axis direction using the following formula.
  • the evaluation results are shown in Table 2.
  • Dichroic ratio (A2) / (A1)
  • Example 2 A polarizing element was produced in the same manner as in Example 1. The evaluation results are summarized in Table 2.
  • polarizing layer A polymerizable liquid crystal (RMM141C, manufactured by Merck & Co., Inc.) 14.4 g and a dichroic dye (G-241, manufactured by Hayashibara Co., Ltd.) 0.58 g are dissolved in MIBK 35.0 g. A product was prepared. The obtained polarizing layer forming composition was spin-coated on the alignment layer at 2000 rpm ⁇ 30 sec, and dried on a hot plate at 65 ° C. for 60 seconds to form a coating film. Next, this coating film was exposed at 500 mJ / cm 2 to obtain a polarizing element.
  • RMM141C polymerizable liquid crystal
  • G-241 manufactured by Hayashibara Co., Ltd.
  • a polarizing element was prepared in the same manner as in Comparative Example 1 except that the dichroic dye of the polarizing layer forming composition was changed to G-207 (manufactured by Hayashibara).
  • the polarizing element obtained by using the polarizing layer forming composition of the present invention does not require an alignment film, simplification of the manufacturing process and reduction of member costs are expected.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polarising Elements (AREA)

Abstract

L'invention fournit une composition polymère qui permet d'obtenir un élément polarisant de dichroïsme élevé y compris sans film orienté. Plus précisément, l'invention fournit une composition polymère qui comprend (A) un polymère de type à chaîne latérale possédant une structure développant une photoréactivité et une structure développant des propriétés cristallines liquides, et (B) un pigment dichroïque ainsi qu'un solvant organique. Il est possible d'obtenir une couche de polarisation de dichroïsme élevé à l'aide d'un procédé de fabrication présentant : une étape au cours de laquelle ladite composition est appliquée sur un substrat, et un film d'application est formé ; une étape au cours de laquelle un rayonnement ultraviolet polarisé irradie le film d'application obtenu ; et une étape au cours de laquelle le film d'application obtenu est chauffé. L'élément polarisant obtenu à l'aide de la composition polymère ne nécessitant pas de film orienté, une simplification de son processus de fabrication et une réduction de coût des composants peuvent être envisagées.
PCT/JP2017/013423 2016-03-31 2017-03-30 Composition de formation de couche de polarisation WO2017170947A1 (fr)

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