WO2014168260A1 - 光学異方層形成用組成物 - Google Patents
光学異方層形成用組成物 Download PDFInfo
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- WO2014168260A1 WO2014168260A1 PCT/JP2014/060886 JP2014060886W WO2014168260A1 WO 2014168260 A1 WO2014168260 A1 WO 2014168260A1 JP 2014060886 W JP2014060886 W JP 2014060886W WO 2014168260 A1 WO2014168260 A1 WO 2014168260A1
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- optically anisotropic
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical group C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- UOYPNWSDSPYOSN-UHFFFAOYSA-N hexahelicene Chemical compound C1=CC=CC2=C(C=3C(=CC=C4C=CC=5C(C=34)=CC=CC=5)C=C3)C3=CC=C21 UOYPNWSDSPYOSN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- FJAAOMWUWOTVHA-UHFFFAOYSA-N oxetan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCO1 FJAAOMWUWOTVHA-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical group C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3016—Polarising elements involving passive liquid crystal elements
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor
Definitions
- the present invention relates to a composition for forming an optically anisotropic layer.
- a member including an optically anisotropic film such as a polarizing plate or a retardation plate is used.
- an optically anisotropic film an optically anisotropic film produced by applying a composition containing a polymerizable liquid crystal compound onto a substrate is known.
- a composition for forming an optically anisotropic layer comprising a polymerizable liquid crystal compound, a photopolymerization initiator, and a solvent having a boiling point of less than 120 ° C. is applied onto an alignment-treated substrate.
- an optically anisotropic film formed by obtaining a coating film and polymerizing a polymerizable liquid crystal compound in the coating film is described.
- An optically anisotropic film produced by applying a conventional composition for forming an optically anisotropic layer onto a substrate has a problem that transparency is lowered due to drying unevenness that occurs when the solvent is dried.
- the present invention includes the following inventions.
- a composition for forming an optically anisotropic layer comprising a polymerizable liquid crystal compound, a photopolymerization initiator, and an ester solvent having a boiling point of 120 to 200 ° C. and a vapor pressure of 0.7 kPa or less.
- the ester solvent is at least one selected from the group consisting of 2-methoxyethyl acetate, 2-ethoxyethyl acetate, and ethyl acetoacetate.
- a polymerizable liquid crystal compound contained in the composition for forming an optically anisotropic layer by applying the composition for forming an optically anisotropic layer according to any one of [1] to [4] to the surface of the alignment film An optically anisotropic film obtained by polymerizing.
- a display device comprising the optically anisotropic film according to any one of [5] to [8].
- a polarizing plate having the laminate according to [11] or [12].
- a display device comprising the laminate according to [11] or [12].
- a highly transparent optically anisotropic film can be produced.
- composition for forming an optically anisotropic layer of the present invention contains a polymerizable liquid crystal compound, a photopolymerization initiator, and an ester solvent having a boiling point of 120 to 200 ° C. and a vapor pressure of 0.7 kPa or less.
- polymerizable liquid crystal compound examples include a compound containing a group represented by the formula (X) (hereinafter sometimes referred to as “compound (X)”).
- compound (X) a group represented by the formula (X)
- P 11 represents a polymerizable group.
- a 11 represents a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group.
- the hydrogen atom contained in the divalent alicyclic hydrocarbon group and divalent aromatic hydrocarbon group is a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group or a nitro group.
- the hydrogen atom contained in the alkyl group having 1 to 6 carbon atoms and the alkoxy group having 1 to 6 carbon atoms may be substituted with a fluorine atom.
- B 11 is —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, —CO—NR 16 —, —NR 16 —CO—, —CO—, -CS- or a single bond is represented.
- R 16 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- E 11 represents an alkanediyl group having 1 to 12 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted with an alkoxy group having 1 to 5 carbon atoms, and hydrogen contained in the alkoxy group The atom may be substituted with a halogen atom.
- —CH 2 — constituting the alkanediyl group may be replaced by —O— or —CO—.
- the number of carbon atoms of the aromatic hydrocarbon group and alicyclic hydrocarbon group of A 11 is preferably in the range of 3 to 18, more preferably in the range of 5 to 12, and preferably 5 or 6. Particularly preferred.
- a 11 is preferably a cyclohexane-1,4-diyl group or a 1,4-phenylene group.
- E 11 is preferably a linear alkanediyl group having 1 to 12 carbon atoms.
- —CH 2 — constituting the alkanediyl group may be replaced by —O—.
- a linear alkanediyl group having 1 to 12 carbon atoms such as: —CH 2 —CH 2 —O—CH 2 —CH 2 —, —CH 2 —CH 2 —
- B 11 is preferably —O—, —S—, —CO—O—, or —O—CO—, and more preferably —CO—O—.
- B 12 and B 13 are each independently —O—, —S—, —C ( ⁇ O) —, —C ( ⁇ O) —O—, —O—C ( ⁇ O) —, —O.
- —C ( ⁇ O) —O— is preferable, and —O— or —O—C ( ⁇ O) —O— is more preferable.
- the polymerizable group represented by P 11 polymerization reactivity, particularly that high photopolymerization reactivity, preferably a radical polymerizable group or a cationically polymerizable group, on the handling is easy, the manufacturing itself of the liquid crystal compound Since it is easy, the polymerizable group is preferably a group represented by the following formulas (P-11) to (P-15). [In the formulas (P-11) to (P-15), R 17 to R 21 each independently represents an alkyl group having 1 to 6 carbon atoms or a hydrogen atom. ]
- P 11 is preferably a group represented by formula (P-14) to formula (P-20), more preferably a vinyl group, a p-stilbene group, an epoxy group or an oxetanyl group. More preferably, the group represented by P 11 -B 11- is an acryloyloxy group or a methacryloyloxy group.
- Examples of compound (X) include compounds represented by formula (I), formula (II), formula (III), formula (IV), formula (V) or formula (VI).
- P 11 -B 11 -E 11 -B 12 -A 11 -B 13 -A 12 -B 14 -A 13 -B 15 -A 14 -B 16 -E 12 -B 17 -P 12 (I) P 11 -B 11 -E 11 -B 12 -A 11 -B 13 -A 12 -B 14 -A 13 -B 15 -A 14 -F 11 (II) P 11 -B 11 -E 11 -B 12 -A 11 -B 13 -A 12 -B 14 -A 13 -B 15 -E 12 -B 17 -P 12 (III) P 11 -B 11 -E 11 -B 12 -A 11 -B 13 -A 12 -B 14 -A 13 -F 11 (IV) P 11 -B 11 -E 11
- F 11 is a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a cyano group, a nitro group, a trifluoromethyl group, a dimethylamino group, a hydroxy group, a methylol group, a formyl group, a sulfo group.
- polymerizable liquid crystal compound examples include “3.8.6 Network (fully cross-linked type)”, “6” of Liquid Crystal Handbook (Edited by Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd., October 30, 2000). .5.1 Liquid Crystal Material b. Polymerizable Nematic Liquid Crystal Material ”compound having a polymerizable group, JP 2010-31223 A, JP 2010-270108 A, JP 2011-6360 A And polymerizable liquid crystal compounds described in JP-A-2011-207765.
- the compound (X) include the following formula (I-1) to formula (I-4), formula (II-1) to formula (II-4), formula (III-1) to formula (III- 26), compounds represented by formula (IV-1) to formula (IV-26), formula (V-1) to formula (V-2) and formula (VI-1) to formula (VI-6). It is done.
- k1 and k2 each independently represents an integer of 2 to 12.
- Photopolymerization initiator examples include benzoin compounds, benzophenone compounds, benzyl ketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, ⁇ -acetophenone compounds, triazine compounds, iodonium salts, and sulfonium salts.
- Irgacure 907, Irgacure 184, Irgacure 651, Irgacure 819, Irgacure 250, Irgacure 369 (all are made by Ciba Japan Co., Ltd.), Sake All BZ, Sake All Z, Sake All BEE (all are all Seiko) Chemical Co., Ltd.), Kayacure BP100 (Nippon Kayaku Co., Ltd.), Kayacure UVI-6992 (Dow), Adekaoptomer SP-152, Adekaoptomer SP-170 (all above, ADEKA Corporation) Product), TAZ-A, TAZ-PP (manufactured by Nippon Siebel Hegner) and TAZ-104 (manufactured by Sanwa Chemical Co., Ltd.).
- ⁇ -acetophenone compounds are preferable, and examples of ⁇ -acetophenone compounds include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholino Phenyl) -2-benzylbutan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butan-1-one and the like, more preferably 2- And methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one.
- Examples of commercially available products of ⁇ -acetophenone compounds include Irgacure 369, 379EG, 907 (above, manufactured by BASF Japan Ltd.), Sequol BEE (manufactured by Seiko Chemical Co., Ltd.), and the like.
- the content of the photopolymerization initiator is usually 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.
- the polymerizable liquid crystal compound can be polymerized without disturbing the alignment of the polymerizable liquid crystal compound.
- the ester solvent in this specification means a carboxylic acid ester that is liquid at 23 ° C. and 1 atm.
- Examples of the ester solvent having a boiling point of 120 to 200 ° C. and a vapor pressure of 0.7 kPa or less include ethylene glycol methyl ether acetate, ⁇ -butyrolactone, propylene glycol methyl ether acetate, 2-methoxyethyl acetate, 2-ethoxyethyl acetate, Examples include 3-methoxybutyl acetate, 2-ethoxyethyl acetate, ethyl acetoacetate, amyl acetate, ethyl lactate, butyl lactate, and isoamyl acetate.
- 2-methoxyethyl acetate 2-ethoxyethyl acetate and ethyl acetoacetate
- 2-methoxyethyl acetate 2-methoxyethyl acetate
- 2-ethoxyethyl acetate and ethyl acetoacetate 2-methoxyethyl acetate
- These solvents may be used alone or in combination. By including these solvents, drying unevenness at the time of drying is reduced, and it becomes possible to form an optical anisotropic layer that is more uniform and excellent in transparency.
- the boiling point in this specification is a value under 1 atmosphere
- the vapor pressure is a value at 23 ° C.
- the composition for forming an optically anisotropic layer may further contain another solvent.
- another solvent what makes the operativity at the time of forming an optically anisotropic film favorable is preferable, for example, an organic solvent is mentioned.
- a solvent capable of dissolving the constituent components of the composition for forming an optical anisotropic layer such as a polymerizable liquid crystal compound, and a solvent inert to the polymerization reaction of the polymerizable liquid crystal compound is more preferable.
- solvents include alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, phenol, etc .; boiling point of ethyl acetate, butyl acetate, etc.
- an ester solvent having a vapor pressure higher than 0.7 kPa ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, methyl amyl ketone, methyl isobutyl ketone, N-methyl-2-pyrrolidinone; pentane, hexane ,
- Non-chlorinated aliphatic hydrocarbon solvents such as heptane; non-chlorinated aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; propylene glycol monomethyl ether Tetrahydrofuran, ether solvents such as dimethoxyethane; include; and chloroform, chlorinated hydrocarbon solvents such as chlorobenzene.
- These other solvents may be used alone or in combination.
- the content of the ester solvent having a boiling point of 120 to 200 ° C. and a vapor pressure of 0.7 kPa or less is usually 10% by mass to 95% by mass with respect to the optical anisotropic layer forming composition, preferably 10%. It is from mass% to 90 mass%, more preferably from 50 mass% to 85 mass%.
- the content of the other organic solvent is usually preferably 10 parts by mass to 10000 parts by mass, more preferably 50 parts by mass to 5000 parts by mass with respect to 100 parts by mass of the solid content.
- Solid content means the sum total of the component remove
- the solid content concentration in the composition for forming an optically anisotropic layer is preferably 1% by mass to 50% by mass, more preferably 2% by mass to 50% by mass, and further preferably 5% by mass to 50% by mass. .
- the content ratio of the ester solvent having a boiling point of 120 to 200 ° C. and a vapor pressure of 0.7 kPa or less and the other solvent is usually 1000: 1 to 5: 1 in terms of ester solvent: other solvent.
- the ratio is preferably 100: 1 to 10: 1.
- the composition for forming an optically anisotropic layer of the present invention preferably contains a reactive additive.
- the reactive additive By including the reactive additive, the adhesion between the optically anisotropic film and the alignment film in the laminate of the present invention is improved, and a laminate in which peeling during processing is suppressed can be obtained.
- the reactive additive is preferably one having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule.
- the “active hydrogen reactive group” as used herein is a group reactive to a group having active hydrogen such as a carboxyl group (—COOH), a hydroxyl group (—OH), an amino group (—NH 2 ), and the like. Typical examples thereof include glycidyl group, oxazoline group, carbodiimide group, aziridine group, imide group, isocyanate group, thioisocyanate group, maleic anhydride group and the like.
- the number of carbon-carbon unsaturated bonds and active hydrogen reactive groups contained in the reactive additive is usually 1 to 20, preferably 1 to 10, respectively.
- the reactive additive it is preferable that at least two active hydrogen reactive groups are present. In this case, a plurality of active hydrogen reactive groups may be the same or different.
- the carbon-carbon unsaturated bond of the reactive additive may be a carbon-carbon double bond, a carbon-carbon triple bond, or a combination thereof, but is preferably a carbon-carbon double bond.
- the reactive additive preferably contains a carbon-carbon unsaturated bond as a vinyl group and / or a (meth) acryl group.
- the active hydrogen reactive group is preferably at least one selected from the group consisting of an epoxy group, a glycidyl group and an isocyanate group, and a reactive additive having an acrylic group and an isocyanate group is particularly preferable.
- reactive additives include compounds having (meth) acrylic groups and epoxy groups, such as methacryloxyglycidyl ether and acryloxyglycidyl ether; (meth) acrylic groups and oxetane, such as oxetane acrylate and oxetane methacrylate.
- a compound having a group a compound having a (meth) acryl group and a lactone group, such as lactone acrylate and lactone methacrylate; a compound having a vinyl group and an oxazoline group, such as vinyl oxazoline and isopropenyl oxazoline; isocyanatomethyl acrylate , Oligomers of compounds having (meth) acrylic groups and isocyanate groups, such as isocyanatomethyl methacrylate, 2-isocyanatoethyl acrylate and 20 isocyanatoethyl methacrylate And the like. Moreover, the compound etc.
- methacryloxyglycidyl ether methacryloxyglycidyl ether, acryloxyglycidyl ether, isocyanatomethyl acrylate, isocyanatomethyl methacrylate, vinyl oxazoline, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate and the above oligomers are preferred, isocyanatomethyl acrylate, 2-isocyanatoethyl acrylate and the aforementioned oligomers are particularly preferred.
- n represents an integer of 1 to 10
- R 1 ′ represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms, or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms.
- Two R 2 ′ in each repeating unit is a group represented by one of —NH— and the other of> N—C ( ⁇ O) —R 3 ′ .
- R 3 ′ represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
- at least one R 3 ′ is a group having a carbon-carbon unsaturated bond.
- a compound represented by the following formula (YY) (hereinafter sometimes referred to as a compound (YY)) is particularly preferred (where n is the same as described above). Meaning).
- a compound (YY) a commercially available product can be used as it is or after purification as necessary.
- Laromer (trademark) LR-9000 (made by BASF Corporation) is mentioned, for example.
- the evaluation of adhesion can be performed by an adhesion test according to JIS-K5600.
- the adhesion test may be performed using a commercially available apparatus such as a cross-cut guide I series (CCI-1, 1 mm interval, for 25 squares) manufactured by Cortec Corporation.
- a cross-cut guide I series (CCI-1, 1 mm spacing, 25 squares) manufactured by Co-Tech Co., Ltd.
- the alignment film on which the optically anisotropic film is formed is peeled from the resin base material. It can be determined that the adhesiveness is high if the mass retained without being 9 masses or more in 25 masses and 36% or more of the mass is not peeled from the resin base material on the basis of area.
- the content of the reactive additive is usually 0.1 to 30 parts by mass, preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.
- composition for forming an optically anisotropic layer may contain a polymerization inhibitor, a photosensitizer, a leveling agent, a chiral agent, and the like.
- Polymerization inhibitor can control the polymerization reaction of the polymerizable liquid crystal compound.
- Polymerization inhibitors include hydroquinones having substituents such as hydroquinone and alkyl ethers; catechols having substituents such as alkyl ethers such as butylcatechol; pyrogallols, 2,2,6,6-tetramethyl-1- Radical scavengers such as piperidinyloxy radicals; thiophenols; ⁇ -naphthylamines and ⁇ -naphthols.
- the content of the polymerization inhibitor in the composition for forming an optically anisotropic layer is usually 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound. Part by mass. If it is in the said range, since it can superpose
- Photosensitizer examples include xanthones such as xanthone and thioxanthone; anthracene having a substituent such as anthracene and alkyl ether; phenothiazine; and rubrene.
- the photosensitizer can increase the sensitivity of the photopolymerization initiator.
- the content of the photosensitizer is usually 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.
- Leveling agent examples include organic modified silicone oil-based, polyacrylate-based and perfluoroalkyl-based leveling agents. Specifically, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all are manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341, X22-161A, KF6001 (all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (all, Momentive Performance Materials Japan GK) Manufactured), Fluorinert (registered trademark) FC-72, FC-40, FC-43, FC-3283 (above, Manufactured by Sumitomo 3M Co
- a smoother optically anisotropic film can be formed by the leveling agent. Moreover, the flowability of the composition for forming an optically anisotropic layer can be controlled and the crosslink density of the optically anisotropic layer can be adjusted during the production process of the optically anisotropic film.
- the content of the leveling agent is usually 0.1 to 30 parts by mass, preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.
- chiral agent examples include known chiral agents (for example, liquid crystal device handbook, Chapter 3-4-3, TN, chiral agent for STN, 199 pages, edited by Japan Society for the Promotion of Science, 142nd Committee, 1989). It is done.
- the chiral agent generally contains an asymmetric carbon atom, but an axially asymmetric compound or a planar asymmetric compound containing no asymmetric carbon atom can also be used as the chiral agent.
- the axial asymmetric compound or the planar asymmetric compound include binaphthyl, helicene, paracyclophane, and derivatives thereof.
- PALIOCOLOR (registered trademark) LC756 manufactured by BASF Japan Ltd. are preferable.
- the content thereof is usually 0.1 to 30 parts by mass, preferably 1.0 to 25 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound. If it is in the said range, since it can superpose
- the optically anisotropic film of the present invention is obtained by coating the composition for forming an optical anisotropic layer on the surface of an alignment film and polymerizing a polymerizable liquid crystal compound contained in the composition for forming an optical anisotropic layer. Is obtained.
- the alignment film is usually formed on a substrate.
- a transparent substrate is usually used.
- a transparent substrate means a substrate having translucency capable of transmitting light, particularly visible light, and the translucency is a transmittance with respect to a light beam having a wavelength of 380 to 780 nm of 80% or more.
- Specific examples of the transparent substrate include glass and a translucent resin substrate, and a translucent resin substrate is preferable.
- the substrate is usually a film.
- the resin constituting the translucent resin base material examples include polyolefins such as polyethylene, polypropylene and norbornene polymers; polyvinyl alcohol; polyethylene terephthalate; polymethacrylic acid ester; polyacrylic acid ester; cellulose ester; polyethylene naphthalate; And sulfone; polyether sulfone; polyether ketone; polyphenylene sulfide; and polyphenylene oxide.
- a substrate made of polyolefin such as polyethylene, polypropylene, norbornene-based polymer is preferable.
- the substrate may be surface treated.
- the surface treatment include a method of treating the surface of the substrate with corona or plasma under vacuum or atmospheric pressure, a method of laser treating the surface of the substrate, a method of treating the surface of the substrate with ozone, and a surface of the substrate.
- primer treatment method for applying a coupling agent to the substrate surface, reactive monomers and reactive polymers are attached to the substrate surface, Examples thereof include a graft polymerization method in which a reaction is performed by irradiation with radiation, plasma or ultraviolet rays. Among them, a method of corona or plasma treatment of the substrate surface under vacuum or atmospheric pressure is preferable.
- a method of performing a surface treatment of a substrate by installing a substrate between opposed electrodes under a pressure near atmospheric pressure and generating corona or plasma, A method of flowing a gas between the electrodes facing each other, converting the gas into a plasma between the electrodes, and spraying the plasmad gas onto the substrate; and There is a method in which glow discharge plasma is generated under low pressure conditions to perform surface treatment of the substrate.
- a substrate is placed between opposed electrodes, and corona or plasma is generated to treat the surface of the substrate, or a gas is flowed between the opposed electrodes.
- a method is preferred in which the gas is converted into plasma and the plasmaized gas is sprayed onto the substrate.
- Such surface treatment with corona or plasma is usually performed by a commercially available surface treatment apparatus.
- a method of forming an alignment film on the substrate a method of applying an orientation polymer to the surface of the substrate and drying, a method of applying an orientation polymer and drying and rubbing the surface, and applying and drying a photo-alignment polymer And a method of forming a monomolecular film having a long-chain alkyl group using the Langmuir-Blodgett method (LB method).
- LB method Langmuir-Blodgett method
- the method of applying and drying the alignment polymer, and applying and drying the alignment polymer and the surface thereof A method of rubbing is preferred.
- the alignment polymer and the photo-alignment polymer are usually applied after being dissolved in a solvent.
- the alignment film in the present specification does not dissolve in the composition for forming an optical anisotropic layer, but is heated by adjusting the liquid crystal alignment of the polymerizable liquid crystal compound by removing the solvent contained in the composition for forming the optical anisotropic layer. Those that do not change in quality and do not peel off due to friction during film conveyance are preferred.
- alignment polymer examples include polyamides and gelatins having an amide bond in the molecule, polyimides having an imide bond in the molecule and polyamic acid, polyvinyl alcohol, alkyl-modified polyvinyl alcohol, polyacrylamide, polyoxazole, Examples include polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid or polyacrylic acid esters. These polymers may be one type, a composition combining a plurality of types of polymers, or a copolymer combining a plurality of types of polymers. Among these, polyamide, polyimide, or polyamic acid is preferable.
- polymers can be easily produced by polycondensation such as dehydration and deamination, chain polymerization such as radical polymerization, anion polymerization, and cation polymerization, coordination polymerization, and ring-opening polymerization.
- orientation polymers include Sanever (registered trademark, manufactured by Nissan Chemical Industries), Optomer (registered trademark, manufactured by JSR), and the like.
- An alignment film formed from such an alignment polymer facilitates liquid crystal alignment of the polymerizable liquid crystal compound.
- various liquid crystal alignments such as horizontal alignment, vertical alignment, hybrid alignment, and tilt alignment can be controlled depending on the type of alignment polymer and rubbing conditions, and can be used to improve the viewing angle of various liquid crystal panels.
- Examples of the photo-alignment polymer include a polymer having a photosensitive structure.
- a polymer having a photosensitive structure When a polymer having a photosensitive structure is irradiated with polarized light, the photosensitive structure in the irradiated portion is isomerized or cross-linked so that the photo-alignable polymer is aligned, and an alignment regulating force is imparted to the film made of the photo-alignable polymer.
- the Examples of the photosensitive structure include an azobenzene structure, a maleimide structure, a chalcone structure, a cinnamic acid structure, a 1,2-vinylene structure, a 1,2-acetylene structure, a spiropyran structure, a spirobenzopyran structure, and a fulgide structure.
- the photo-alignment polymer that forms the alignment film may be one type, a combination of a plurality of polymers having different structures, or a copolymer having a plurality of different photosensitive structures.
- a photo-alignment polymer is produced by subjecting a monomer having a photosensitive structure to polycondensation such as dehydration and dealcoholization, chain polymerization such as radical polymerization, anionic polymerization, and cationic polymerization, coordination polymerization, or ring-opening polymerization. can do.
- Examples of the photo-alignment polymer include light described in Japanese Patent No. 4450261, Japanese Patent No. 4011652, Japanese Patent Application Laid-Open No. 2010-49230, Japanese Patent No. 444090, Japanese Patent Application Publication No. 2007-156439, Japanese Patent Application Laid-Open No. 2007-232934, and the like.
- An orientation polymer etc. are mentioned.
- the photoalignable polymer those that form a crosslinked structure by irradiation with polarized light are preferable from the viewpoint of durability.
- Solvents that dissolve the alignment polymer or photoalignment polymer include, for example, water; alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve; ethyl acetate, butyl acetate, ethylene glycol methyl Ester solvents such as ether acetate, ⁇ -butyrolactone, propylene glycol methyl ether acetate, ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, methyl isobutyl ketone, N-methyl-2-pyrrolidone; Aliphatic hydrocarbon solvents such as pentane, hexane and heptane; aromatic hydrocarbon solvents such as toluene, xylene and chlorobenzene; nitrile
- the amount of the solvent is usually 10 parts by mass to 100000 parts by mass, preferably 1000 parts by mass to 50000 parts by mass, more preferably 2000 parts by mass to 100 parts by mass with respect to 100 parts by mass of the orientation polymer or photoalignment polymer. It is 20000 parts by mass.
- Examples of the method for dissolving the orientation polymer or the photo-orientation polymer in a solvent and applying the polymer to a substrate include an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a CAP coating method, and a die coating method.
- coating using coaters such as a dip coater, a bar coater, a spin coater, is also mentioned.
- Drying methods include natural drying, ventilation drying, heat drying, vacuum drying, and a combination of these.
- the drying temperature is preferably 10 to 250 ° C, more preferably 25 to 200 ° C.
- the drying time is preferably 5 seconds to 60 minutes, more preferably 10 seconds to 30 minutes, depending on the type of solvent.
- the rubbing method includes a method in which a rubbing roll wound with a rotating rubbing cloth is brought into contact with an oriented polymer that has been applied to a substrate and dried.
- Examples of the method of irradiating polarized light include a method using an apparatus described in JP-A-2006-323060.
- a patterned alignment film can be formed by repeatedly irradiating polarized light such as linearly polarized ultraviolet light for each region through a photomask corresponding to a desired plurality of regions.
- polarized light such as linearly polarized ultraviolet light
- a photomask usually, a light shielding pattern provided on a film of quartz glass, soda lime glass or polyester is used. The portion covered with the light-shielding pattern blocks the irradiated polarized light, and the portion not covered transmits the irradiated polarized light. Quartz glass is preferable in that the influence of thermal expansion is small.
- the irradiated polarized light is preferably ultraviolet light.
- the thickness of the alignment film is usually 10 nm to 10000 nm, preferably 10 nm to 1000 nm.
- the polymerizable liquid crystal compound can be easily aligned in a desired direction or angle, which is preferable.
- An optical anisotropic layer forming composition is applied to the alignment film surface to polymerize the polymerizable liquid crystal compound contained in the optical anisotropic layer forming composition, or it is applied and dried to form an optical anisotropic layer.
- An optically anisotropic film is obtained by polymerizing the polymerizable liquid crystal compound contained in the composition.
- the optically anisotropic film exhibits a liquid crystal phase such as a nematic phase, it has birefringence due to monodomain alignment. Since the liquid crystal alignment of the polymerizable liquid crystal compound is fixed, the optically anisotropic film of the present invention is hardly affected by changes in birefringence due to heat.
- the thickness of the optically anisotropic film can be adjusted as appropriate depending on the application, but is preferably 0.1 ⁇ m to 10 ⁇ m, and more preferably 0.2 ⁇ m to 5 ⁇ m from the viewpoint of reducing photoelasticity.
- optically anisotropic film examples include a retardation film and a polarizing film.
- a retardation film can be obtained by polymerizing a polymerizable liquid crystal compound in a vertical or horizontal alignment.
- Vertical alignment means having the major axis of the liquid crystal compound in a direction perpendicular to the substrate surface
- horizontal alignment means having the major axis of the liquid crystal compound in a direction parallel to the substrate surface.
- the liquid crystal alignment of the polymerizable liquid crystal compound is controlled by the properties of the alignment film and the polymerizable liquid crystal compound.
- the alignment film is a material having an alignment regulating force that develops horizontal alignment
- the polymerizable liquid crystal compound can form a horizontal alignment or a hybrid alignment, and can be a material having an alignment regulating force that develops vertical alignment.
- the polymerizable liquid crystal compound can form a vertical alignment or an inclined alignment.
- the alignment regulating force can be arbitrarily adjusted depending on the surface state and rubbing conditions, for example, when the alignment film is formed of an alignment polymer, and when the alignment film is formed of a photo-alignment polymer, It is possible to adjust arbitrarily according to irradiation conditions.
- the liquid crystal alignment can also be controlled by selecting physical properties such as surface tension and liquid crystallinity of the polymerizable liquid crystal compound.
- Examples of methods for applying the optically anisotropic layer forming composition onto the alignment film include extrusion coating, direct gravure coating, reverse gravure coating, CAP coating, slit coating, and die coating.
- coating using coaters such as a dip coater, a bar coater, a spin coater, etc. are mentioned.
- a CAP coating method, an ink jet method, a dip coating method, a slit coating method, a die coating method, and a coating method using a bar coater are preferable because they can be continuously applied in a Roll to Roll format.
- drying method examples include the same methods as the drying method at the time of forming the alignment film. Of these, natural drying or heat drying is preferred.
- the drying temperature is usually in the range of 0 ° C to 250 ° C, preferably in the range of 50 ° C to 220 ° C, and more preferably in the range of 80 ° C to 170 ° C.
- the drying time is usually 10 seconds to 60 minutes, preferably 30 seconds to 30 minutes.
- a photopolymerization method is preferable.
- the photopolymerization method is preferable from the viewpoint of the heat resistance of the substrate because the polymerization can be carried out at a low temperature.
- the photopolymerization reaction is usually performed by irradiating visible light, ultraviolet light or laser light, preferably ultraviolet light.
- the light irradiation is preferably performed after drying and removing the solvent contained in the applied optically anisotropic layer forming composition.
- the drying may be performed in parallel with the light irradiation, but it is preferable to remove most of the solvent before the light irradiation.
- the alignment film When the alignment film is formed on the base material, a laminate having the base material, the alignment film, and the optical anisotropic film in this order can be obtained by forming the optical anisotropic film on the surface of the alignment film. Since the laminate of the present invention is excellent in transparency in the visible light region, it is useful as a member for various display devices.
- the optical anisotropic film which does not have a base material or a base material and an alignment film is normally combined with other members, such as a polarizing film, via an adhesive agent.
- a method of combining with other members via an adhesive a method of bonding an optically anisotropic film having no base material or a base material and an alignment film to other members using an adhesive, and A method of removing the base material or the base material and the orientation film after the optically anisotropic film formed on the surface of the orientation film formed on the surface of the base material is bonded to another member using an adhesive, etc.
- the adhesive may be applied to the optically anisotropic film or may be applied to other members.
- the arithmetic average roughness of the surface of the optically anisotropic film of the present invention is usually 100 nm or less, preferably 50 nm or less, more preferably 40 nm or less, and further preferably 30 nm or less.
- the arithmetic average roughness (Ra) can be calculated, for example, with the attached software in cross-sectional observation using a commercially available laser microscope, and the arithmetic average roughness (Ra) in this specification is calculated when the parameters are calculated.
- the cut-off wavelength is calculated as 1/50 of the image viewing width
- the reference length is calculated as the viewing width of the image.
- the arithmetic average roughness (Ra) is calculated according to the following formula. In the formula, Ra represents an arithmetic average roughness, l represents a reference length, and f (x) represents a roughness curve.
- a viewing angle compensation film By laminating a plurality of the laminates of the present invention, combining the laminate of the present invention with another film, or combining the optically anisotropic film of the present invention and another member, a viewing angle compensation film, a field of view It can be used as a corner enlargement film, an antireflection film, a polarizing plate, a circular polarizing plate, an elliptical polarizing plate, or a brightness enhancement film.
- the optically anisotropic film of the present invention which is a retardation film, and the laminate having the optically anisotropic film, convert linearly polarized light into circularly polarized light or elliptically polarized light when confirmed from the oblique angle on the light exit side. It is particularly useful as an optical material for converting circularly polarized light or elliptically polarized light into linearly polarized light, or converting the polarization direction of linearly polarized light.
- the optically anisotropic film of the present invention which is a retardation film, and a laminate having the optically anisotropic film include a VA (vertical alignment) mode, an IPS (in-plane switching) mode, and an OCB (optically compensated bend) mode.
- VA vertical alignment
- IPS in-plane switching
- OCB optical compensated bend
- TN twisted nematic
- STN super twisted nematic
- the refractive index in a slow axis direction in a plane n x the refractive index in a direction (a fast axis direction) perpendicular to the slow axis in the plane n y
- the refractive index in the thickness direction is nz .
- the optically anisotropic film and laminate of the present invention are particularly preferably used as a positive C plate.
- the front retardation value Re may be adjusted in the range of 0 to 10 nm, preferably in the range of 0 to 5 nm.
- the direction retardation value R th may be adjusted in the range of ⁇ 10 to ⁇ 300 nm, preferably in the range of ⁇ 20 to ⁇ 200 nm, and is particularly preferably selected according to the characteristics of the liquid crystal cell.
- the thickness direction retardation value R th which means the refractive index anisotropy in the thickness direction of the optically anisotropic film is a retardation value R 50 measured by inclining 50 degrees with the in-plane fast axis as the tilt axis. And the in-plane retardation value R 0 .
- the retardation value R th in the thickness direction is the in-plane retardation value R 0
- the thickness d of the retardation film and the position the average refractive index n 0 of the retardation film, obtains the n x, n y and nz by the following equation (9) to (11), these are substituted into equation (8) can be calculated.
- Rth [( nx + ny ) / 2- nz ] * d (8)
- R 0 (n x -n y ) ⁇ d (9)
- ny ′ ny ⁇ nz / [ ny 2 ⁇ sin 2 ( ⁇ ) + nz 2 ⁇ cos 2 ( ⁇ )] 1/2
- optically anisotropic film and laminate of the present invention are also useful as members constituting a polarizing plate.
- a polarizing plate 4a shown in FIG. 1 (a) is a polarizing plate in which a retardation film 1 and a polarizing film 2 are directly laminated, and a polarizing plate 4b shown in FIG. 1 (b) is a retardation film. 1 and the polarizing film 2 are the polarizing plates bonded together through adhesive layer 3 '.
- a polarizing plate 4c shown in FIG. 1 (c) is a polarizing plate in which a retardation film 1 and a retardation film 1 ′ are laminated, and further, a retardation film 1 ′ and a polarizing film 2 are laminated.
- a polarizing plate 4d shown in FIG. 1 (d) is obtained by laminating a retardation film 1 and a retardation film 1 ′ via an adhesive layer 3, and further laminating a polarizing film 2 on the retardation film 1 ′. It is the made polarizing plate.
- a polarizing plate 4e shown in FIG. 1 (e) is obtained by bonding a retardation film 1 and a retardation film 1 ′ through an adhesive layer 3, and further bonding the retardation film 1 ′ and the polarizing film 2 together. It is a polarizing plate bonded through an agent layer 3 ′.
- the adhesive in this specification means a general term for an adhesive and / or an adhesive.
- Said retardation film and polarizing film may have a base material, and do not need to have it.
- the optically anisotropic film and laminate of the present invention in which the optically anisotropic film is a retardation film can be used for the retardation films 1 and 1 ′, and the optically anisotropic film is polarized on the polarizing film 2.
- the optically anisotropic film and laminate of the present invention, which are films, can be used.
- the polarizing film 2 may be a film having a polarizing function.
- the polarizing film include a stretched film on which a dye having absorption anisotropy is adsorbed and a film coated with a dye having absorption anisotropy.
- the dye having absorption anisotropy include dichroic dyes such as iodine and azo compounds.
- a stretched film on which a dye having absorption anisotropy is adsorbed a film obtained by adsorbing a dichroic dye on a polyvinyl alcohol film and a film obtained by adsorbing a dichroic dye by stretching the polyvinyl alcohol film
- polarizing films described in Japanese Patent No. 3770862, Japanese Patent No. 4432487, and the like include polarizing films described in Japanese Patent No. 3770862, Japanese Patent No. 4432487, and the like.
- a film coated with a dye having absorption anisotropy a film obtained by applying a composition containing a dichroic dye having liquid crystallinity or a composition containing a dichroic dye and a polymerizable liquid crystal compound, etc.
- the polarizing film as described in Unexamined-Japanese-Patent No. 2012-33249 etc. is mentioned.
- the polarizing film preferably has a protective film on one side or both sides thereof.
- Examples of the protective film include the same ones as described above.
- the adhesive forming the adhesive layer 3 and the adhesive layer 3 ′ is preferably an adhesive having high transparency and excellent heat resistance.
- adhesives include acrylic adhesives, epoxy adhesives, and urethane adhesives.
- the optically anisotropic film and laminate of the present invention can be used for display devices.
- the display device include a liquid crystal display device including a liquid crystal panel in which the optically anisotropic film or laminate of the present invention and a liquid crystal panel are bonded, and the optically anisotropic film or laminate of the present invention and a light emitting layer.
- EL organic electroluminescence
- a liquid crystal display device will be described as an embodiment of a display device including a polarizing plate having the optically anisotropic film or laminate of the present invention.
- Examples of the liquid crystal display device include liquid crystal display devices 10a and 10b shown in FIGS. 2 (a) and 2 (b).
- the polarizing plate 4 and the liquid crystal panel 6 of the present invention are bonded together via an adhesive layer 5.
- the polarizing plate 4 of the present invention is on one surface of the liquid crystal panel 6, the polarizing plate 4 'of the present invention is on the other surface of the liquid crystal panel 6, and the adhesive layer 5 and It has a structure in which the adhesive layers 5 'are bonded to each other.
- an electrode not shown
- composition for alignment film The composition is shown in Table 1.
- Addition agent LR9000 is added to a solution obtained by adding ⁇ -butyrolactone (GBL) and butyl acetate to Sunever SE-610 (manufactured by Nissan Chemical Industries, Ltd.) (alignment polymer), and composition for forming an alignment film (1) is obtained. It was adjusted.
- Table 1 The values in parentheses in Table 1 represent the ratio of each component in the prepared composition.
- SE-610 the solid content was converted from the concentration described in the delivery specification.
- LR9000 in Table 1 represents Laromer (registered trademark) LR-9000 manufactured by BASF Japan.
- optical anisotropic layer forming composition The components of the optically anisotropic layer forming compositions (1) to (6) shown in Table 2 were mixed. The resulting solution was stirred at 80 ° C. for 1 hour and then cooled to room temperature. .
- the liquid crystal compound (X-1) was produced by the method described in JP 2010-1284 A.
- Irg369 is Irgacure 369 manufactured by BASF Japan
- BYK-361N is a leveling agent manufactured by Big Chemie Japan
- X-1 is a polymerizable liquid crystal compound represented by the following formula (X-1).
- Example 1 The surface of a cycloolefin polymer film (Arton (registered trademark), manufactured by JSR Corporation) is subjected to a condition of an output of 0.3 kW and a processing speed of 3 m / min using a corona treatment device (AGF-B10, manufactured by Kasuga Electric Co., Ltd.) Processed once.
- the alignment film forming composition (1) was applied to the surface subjected to the corona treatment and dried to prepare an alignment film having a thickness of 60 nm.
- the composition (1) for forming a photoanisotropic layer was applied using a bar coater and heated to 105 ° C. to form an unpolymerized film on the alignment film.
- Example 2 Example 3, Comparative Example 1, Comparative Example 2, Comparative Example 3
- the optical anisotropic layer forming composition (1) was changed to the optical anisotropic layer forming composition (2), the optical anisotropic layer forming composition (3), and the optical anisotropic layer forming composition ( 4), except that the composition for forming an optically anisotropic layer (5) or the composition for forming an optically anisotropic layer (6) was carried out under the same conditions as in Example 1, and the laminates (2) to ( 5) was obtained.
- the laminates produced in the examples were excellent in transparency.
- an optically anisotropic film and laminate excellent in transparency can be obtained.
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Abstract
Description
[1] 重合性液晶化合物、光重合開始剤及び沸点が120~200℃でかつ蒸気圧が0.7kPa以下であるエステル溶剤を含む光学異方層形成用組成物。
[2] エステル溶剤が、酢酸2−メトキシエチル、酢酸2−エトキシエチル及びアセト酢酸エチルからなる群から選ばれる少なくとも1種である[1]記載の光学異方層形成用組成物。
[3] 光学異方層形成用組成物に対するエステル溶剤の含有量が10質量%~95質量%である[1]又は[2]に記載の光学異方層形成用組成物。
[4] さらにイソシアネート基を有する化合物を含む、[1]~[3]のいずれかに記載の光学異方層形成用組成物。
[5] [1]~[4]のいずれかに記載の光学異方層形成用組成物を、配向膜の表面に塗布して該光学異方層形成用組成物に含まれる重合性液晶化合物を重合することにより得られる光学異方性フィルム。
[6] 位相差フィルムである[5]に記載の光学異方性フィルム。
[7] 表面の算術平均粗さが100nm以下である[5]又は[6]に記載の光学異方性フィルム。
[8] IPS(in−plane switching)液晶表示装置用の[5]~[7]のいずれかに記載の光学異方性フィルム。
[9] [5]~[8]のいずれかに記載の光学異方性フィルムを有する偏光板。
[10] [5]~[8]のいずれかに記載の光学異方性フィルムを備えた表示装置。
[11] 基材と、配向膜と、[5]~[8]のいずれかに記載の光学異方性フィルムをこの順に有する積層体。
[12] 基材がポリオレフィン樹脂である[11]に記載の積層体。
[13] 配向膜付基材の配向膜表面に、[1]~[4]のいずれかに記載の光学異方層形成用組成物を塗布し、乾燥し、光照射する積層体の製造方法。
[14] [11]又は[12]に記載の積層体を有する偏光板。
[15] [11]又は[12]に記載の積層体を備えた表示装置。
重合性液晶化合物としては、例えば、式(X)で表される基を含む化合物(以下「化合物(X)」という場合がある)が挙げられる。
P11−B11−E11−B12−A11−B13− (X)
[式(X)中、P11は、重合性基を表わす。
A11は、2価の脂環式炭化水素基または2価の芳香族炭化水素基を表わす。該2価の脂環式炭化水素基および2価の芳香族炭化水素基に含まれる水素原子は、ハロゲン原子、炭素数1~6のアルキル基、炭素数1~6アルコキシ基、シアノ基またはニトロ基で置換されていてもよく、該炭素数1~6のアルキル基および該炭素数1~6アルコキシ基に含まれる水素原子は、フッ素原子で置換されていてもよい。
B11は、−O−、−S−、−CO−O−、−O−CO−、−O−CO−O−、−CO−NR16−、−NR16−CO−、−CO−、−CS−または単結合を表わす。R16は、水素原子または炭素数1~6のアルキル基を表わす。
B12およびB13は、それぞれ独立に、−C≡C−、−CH=CH−、−CH2−CH2−、−O−、−S−、−C(=O)−、−C(=O)−O−、−O−C(=O)−、−O−C(=O)−O−、−CH=N−、−N=CH−、−N=N−、−C(=O)−NR16−、−NR16−C(=O)−、−OCH2−、−OCF2−、−CH2O−、−CF2O−、−CH=CH−C(=O)−O−、−O−C(=O)−CH=CH−または単結合を表わす。
E11は、炭素数1~12のアルカンジイル基を表わし、該アルカンジイル基に含まれる水素原子は、炭素数1~5のアルコキシ基で置換されていてもよく、該アルコキシ基に含まれる水素原子は、ハロゲン原子で置換されていてもよい。また、該アルカンジイル基を構成する−CH2−は、−O−または−CO−に置き換わっていてもよい。]
具体的には、メチレン基、エチレン基、プロパン−1,3−ジイル基、ブタン−1,4−ジイル基、ペンタン−1,5−ジイル基、ヘキサン−1,6−ジイル基、ヘプタン−1,7−ジイル基、オクタン−1,8−ジイル基、ノナン−1,9−ジイル基、デカン−1,10−ジイル基、ウンデカン−1,11−ジイル基およびドデカン−1,12−ジイル基等の炭素数1~12の直鎖状アルカンジイル基;−CH2−CH2−O−CH2−CH2−、−CH2−CH2−O−CH2−CH2−O−CH2−CH2−および−CH2−CH2−O−CH2−CH2−O−CH2−CH2−O−CH2−CH2−等が挙げられる。
B11としては、−O−、−S−、−CO−O−、−O−CO−が好ましく、中でも、−CO−O−がより好ましい。
B12およびB13としては、それぞれ独立に、−O−、−S−、−C(=O)−、−C(=O)−O−、−O−C(=O)−、−O−C(=O)−O−が好ましく、中でも、−O−または−O−C(=O)−O−がより好ましい。
[式(P−11)~(P−15)中、
R17~R21はそれぞれ独立に、炭素数1~6のアルキル基または水素原子を表わす。]
P11−B11−で表わされる基が、アクリロイルオキシ基またはメタアクリロイルオキシ基であることがさらに好ましい。
P11−B11−E11−B12−A11−B13−A12−B14−A13−B15−A14−B16−E12−B17−P12 (I)
P11−B11−E11−B12−A11−B13−A12−B14−A13−B15−A14−F11 (II)
P11−B11−E11−B12−A11−B13−A12−B14−A13−B15−E12−B17−P12 (III)
P11−B11−E11−B12−A11−B13−A12−B14−A13−F11 (IV)
P11−B11−E11−B12−A11−B13−A12−B14−E12−B17−P12 (V)
P11−B11−E11−B12−A11−B13−A12−F11 (VI)
(式中、
A12~A14はそれぞれ独立に、A11と同義であり、B14~B16はそれぞれ独立に、B12と同義であり、B17は、B11と同義であり、E12は、E11と同義である。
F11は、水素原子、炭素数1~13のアルキル基、炭素数1~13のアルコキシ基、シアノ基、ニトロ基、トリフルオロメチル基、ジメチルアミノ基、ヒドロキシ基、メチロール基、ホルミル基、スルホ基(−SO3H)、カルボキシ基、炭素数1~10のアルコキシカルボニル基またはハロゲン原子を表わし、該アルキル基およびアルコキシ基を構成する−CH2−は、−O−に置き換っていてもよい。)
光重合開始剤としては、例えば、ベンゾイン化合物、ベンゾフェノン化合物、ベンジルケタール化合物、α−ヒドロキシケトン化合物、α−アミノケトン化合物、α−アセトフェノン化合物、トリアジン化合物、ヨードニウム塩およびスルホニウム塩が挙げられる。具体的には、イルガキュア(Irgacure)907、イルガキュア184、イルガキュア651、イルガキュア819、イルガキュア250、イルガキュア369(以上、全てチバ・ジャパン株式会社製)、セイクオールBZ、セイクオールZ、セイクオールBEE(以上、全て精工化学株式会社製)、カヤキュアー(kayacure)BP100(日本化薬株式会社製)、カヤキュアーUVI−6992(ダウ社製)、アデカオプトマーSP−152、アデカオプトマーSP−170(以上、全て株式会社ADEKA製)、TAZ−A、TAZ−PP(以上、日本シイベルヘグナー社製)およびTAZ−104(三和ケミカル社製)を挙げることができる。中でも、α−アセトフェノン化合物が好ましく、α−アセトフェノン化合物としては、2−メチル−2−モルホリノ−1−(4−メチルスルファニルフェニル)プロパン−1−オン、2−ジメチルアミノ−1−(4−モルホリノフェニル)−2−ベンジルブタン−1−オン及び2−ジメチルアミノ−1−(4−モルホリノフェニル)−2−(4−メチルフェニルメチル)ブタン−1−オン等が挙げられ、より好ましくは2−メチル−2−モルホリノ−1−(4−メチルスルファニルフェニル)プロパン−1−オン及び2−ジメチルアミノ−1−(4−モルホリノフェニル)−2−ベンジルブタン−1−オンが挙げられる。α−アセトフェノン化合物の市販品としては、イルガキュア369、379EG、907(以上、BASFジャパン(株)製)及びセイクオールBEE(精工化学社製)等が挙げられる。
本明細書におけるエステル溶剤とは、23℃、1気圧下において液体である、カルボン酸エステルのことをいう。
沸点が120~200℃でかつ蒸気圧が0.7kPa以下であるエステル溶剤としては、エチレングリコールメチルエーテルアセテート、γ−ブチロラクトン、プロピレングリコールメチルエーテルアセテート、酢酸2−メトキシエチル、酢酸2−エトキシエチル、酢酸3−メトキシブチル、酢酸2−エトキシエチル、アセト酢酸エチル、酢酸アミル、乳酸エチル、乳酸ブチル、酢酸イソアミル等が挙げられる。好ましくは酢酸2−メトキシエチル、酢酸2−エトキシエチル及びアセト酢酸エチルであり、より好ましくは酢酸2−メトキシエチルである。これらの溶剤は単独で用いてもよいし、組み合わせてもよい。これらの溶剤を含むことで、乾燥時の乾燥ムラが低減され、より均一で透明性に優れた光学異方層を形成することが可能となる。
なお、本明細書における沸点は1気圧下での値であり、蒸気圧は23℃での値である。
他の溶剤としては、光学異方性フィルムを形成する際の操作性を良好にするものが好ましく、例えば、有機溶剤が挙げられる。中でも、重合性液晶化合物等の光学異方層形成用組成物の構成成分を溶解し得る溶剤であって、且つ、重合性液晶化合物の重合反応に不活性な溶剤がより好ましい。
具体的な他の溶剤としては、メタノール、エタノール、エチレングリコール、イソプロピルアルコール、プロピレングリコール、メチルセロソルブ、ブチルセロソルブ、プロピレングリコールモノメチルエーテル、フェノール等のアルコール溶剤;酢酸エチル、酢酸ブチル等の沸点が120℃未満又は蒸気圧が0.7kPaよりも高いエステル溶剤;アセトン、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、シクロヘプタノン、メチルアミルケトン、メチルイソブチルケトン、N−メチル−2−ピロリジノン等のケトン溶剤;ペンタン、ヘキサン、ヘプタン等の非塩素化脂肪族炭化水素溶剤;トルエン、キシレン等の非塩素化芳香族炭化水素溶剤;アセトニトリル等のニトリル溶剤;プロピレングリコールモノメチルエーテル、テトラヒドロフラン、ジメトキシエタン等のエーテル溶剤;およびクロロホルム、クロロベンゼン等の塩素化炭化水素溶剤;が挙げられる。これら他の溶剤は、単独で用いてもよいし、組み合わせてもよい。
本発明の光学異方層形成用組成物は、好ましくは反応性添加剤を含む。
反応性添加剤を含むことにより、本発明の積層体における光学異方性フィルムと配向膜との密着性が向上し、加工時の剥離が抑制された積層体を得ることができる。
[式(Y)中、
nは1~10までの整数を表わし、R1’は、炭素数2~20の2価の脂肪族又は脂環式炭化水素基、或いは炭素数5~20の2価の芳香族炭化水素基を表わす。各繰り返し単位にある2つのR2’は、一方が−NH−であり、他方が>N−C(=O)−R3’で示される基である。R3’は、水酸基又は炭素−炭素不飽和結合を有する基を表す。
式(Y)中のR3’のうち、少なくとも1つのR3’は炭素−炭素不飽和結合を有する基である。]
化合物(YY)には、市販品をそのまま又は必要に応じて精製して用いることができる。市販品としては、例えば、Laromer(登録商標)LR−9000(BASF社製)が挙げられる。
例えば、コーテック株式会社製クロスカットガイドIシリーズ(CCI−1、1mm間隔、25マス用)を用いて、密着性試験を行い、光学異方性フィルムが形成された配向膜が樹脂基材から剥離せずに保持されるマスが、25マス中9マス以上であり、面積基準で、36%以上が樹脂基材から剥離しない状態であれば密着性が高いと判断できる。
重合禁止剤は、重合性液晶化合物の重合反応をコントロールすることができる。
重合禁止剤としては、ハイドロキノンおよびアルキルエーテル等の置換基を有するハイドロキノン類;ブチルカテコール等のアルキルエーテル等の置換基を有するカテコール類;ピロガロール類、2,2,6,6−テトラメチル−1−ピペリジニルオキシラジカル等のラジカル補足剤;チオフェノール類;β−ナフチルアミン類およびβ−ナフトール類が挙げられる。
光学異方層形成用組成物における重合禁止剤の含有量は、重合性液晶化合物100質量部に対して、通常0.1質量部~30質量部であり、好ましくは0.5質量部~10質量部である。上記範囲内であれば、重合性液晶化合物の配向を乱すことなく、重合することができるため好ましい。
光増感剤としては、キサントン、チオキサントン等のキサントン類;アントラセンおよびアルキルエーテル等の置換基を有するアントラセン類;フェノチアジン;ルブレンが挙げられる。
光増感剤は、光重合開始剤を高感度化することができる。光増感剤の含有量は、重合性液晶化合物100質量部に対して、通常0.1質量部~30質量部であり、好ましくは0.5質量部~10質量部である。
レベリング剤としては、有機変性シリコーンオイル系、ポリアクリレート系およびパーフルオロアルキル系のレベリング剤が挙げられる。具体的には、DC3PA、SH7PA、DC11PA、SH28PA、SH29PA、SH30PA、ST80PA、ST86PA、SH8400、SH8700、FZ2123(以上、全て東レ・ダウコーニング(株)製)、KP321、KP323、KP324、KP326、KP340、KP341、X22−161A、KF6001(以上、全て信越化学工業(株)製)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF−4446、TSF4452、TSF4460(以上、全てモメンティブ パフォーマンス マテリアルズ ジャパン合同会社製)、フロリナート(fluorinert)(登録商標)FC−72、同FC−40、同FC−43、同FC−3283(以上、全て住友スリーエム(株)製)、メガファック(登録商標)R−08、同R−30、同R−90、同F−410、同F−411、同F−443、同F−445、同F−470、同F−477、同F−479、同F−482、同F−483(以上、いずれもDIC(株)製)、エフトップ(商品名)EF301、同EF303、同EF351、同EF352(以上、全て三菱マテリアル電子化成(株)製)、サーフロン(登録商標)S−381、同S−382、同S−383、同S−393、同SC−101、同SC−105、KH−40、SA−100(以上、全てAGCセイミケミカル(株)製)、商品名E1830、同E5844((株)ダイキンファインケミカル研究所製)、BM−1000、BM−1100、BYK−352、BYK−353、BYK−361N(いずれも商品名:BM Chemie社製)が挙げられる。2種以上のレベリング剤を組み合わせてもよい。
カイラル剤としては、公知のカイラル剤(例えば、液晶デバイスハンドブック、第3章4−3項、TN、STN用カイラル剤、199頁、日本学術振興会第142委員会編、1989に記載)が挙げられる。
カイラル剤は、一般に不斉炭素原子を含むが、不斉炭素原子を含まない軸性不斉化合物あるいは面性不斉化合物もカイラル剤として用いることができる。軸性不斉化合物または面性不斉化合物としては、ビナフチル、ヘリセン、パラシクロファンおよびこれらの誘導体が挙げられる。
具体的には、特開2007−269640号公報、特開2007−269639号公報、特開2007−176870号公報、特開2003−137887号公報、特表2000−515496号公報、特開2007−169178号公報および特表平9−506088号公報に記載されているような化合物が挙げられ、好ましくはBASFジャパン(株)製のpaliocolor(登録商標)LC756である。
カイラル剤を用いる場合、その含有量は、重合性液晶化合物100質量部に対して、通常0.1質量部~30質量部であり、好ましくは1.0質量部~25質量部である。上記範囲内であれば、重合性液晶化合物の配向を乱すことなく、重合することができるため好ましい。
基材としては、通常、透明基材が用いられる。透明基材とは、光、特に可視光を透過し得る透光性を有する基材を意味し、透光性とは、波長380~780nmにわたる光線に対しての透過率が80%以上となる特性をいう。具体的な透明基材としては、ガラスおよび透光性樹脂基材が挙げられ、透光性樹脂基材が好ましい。基材は、通常、フィルム状のものが用いられる。
大気圧近傍の圧力下で、対向した電極間に基材を設置し、コロナまたはプラズマを発生させて、基材の表面処理を行う方法、
対向した電極間にガスを流し、電極間でガスをプラズマ化し、プラズマ化したガスを基材に吹付ける方法、および、
低圧条件下で、グロー放電プラズマを発生させて、基材の表面処理を行う方法が挙げられる。
配向性ポリマー及び光配向性ポリマーは、通常、溶剤に溶解して塗布される。
市販の配向性ポリマーとしては、サンエバー(登録商標、日産化学社製)、オプトマー(登録商標、JSR製)等が挙げられる。
このような配向性ポリマーから形成される配向膜は、重合性液晶化合物の液晶配向を容易にする。また、配向性ポリマーの種類やラビング条件によって、水平配向、垂直配向、ハイブリッド配向、傾斜配向等の様々な液晶配向の制御が可能であり、各種液晶パネルの視野角改善等に利用できる。
配向膜の厚さが上記範囲にあると、重合性液晶化合物を所望の方向や角度に容易に液晶配向させることができるため好ましい。
重合性液晶化合物を垂直または水平配向させて重合することで位相差フィルムが得られる。垂直配向とは基材面に対して垂直な方向に液晶化合物の長軸を有することを意味し、水平配向とは基材面に対して平行な方向に液晶化合物の長軸を有することを意味する。
例えば、配向膜が水平配向を発現させる配向規制力を有する材料であれば、重合性液晶化合物は水平配向またはハイブリッド配向を形成することができ、垂直配向を発現させる配向規制力を有する材料であれば、重合性液晶化合物は垂直配向または傾斜配向を形成することができる。
配向規制力は、例えば、配向膜が配向性ポリマーから形成されている場合は、表面状態やラビング条件によって任意に調整することが可能であり、光配向性ポリマーから形成されている場合は、偏光照射条件等によって任意に調整することが可能である。また、重合性液晶化合物の、表面張力や液晶性等の物性を選択することにより、液晶配向を制御することもできる。
基材、又は、基材及び配向膜を有さない光学異方性フィルムは、通常、接着剤を介して偏光フィルム等のその他の部材と組み合わされる。
接着剤を介してその他の部材と組み合わせる方法としては、基材、又は、基材及び配向膜を有さない光学異方性フィルムを、接着剤を用いてその他の部材へ貼合する方法、及び、基材表面に形成された配向膜の表面に形成された光学異方性フィルムを、接着剤を用いてその他の部材へ貼合した後に基材、又は、基材及び配向膜を取り除く方法等が挙げられる。この際、接着剤は、光学異方性フィルムに塗布されてもよく、その他の部材に塗布されてもよい。
具体的には、算術平均粗さ(Ra)は、下記式にしたがって算出される。
式中、Raは算術平均粗さを、lは基準長さを、f(x)は粗さ曲線を表す。
つまり、算術平均粗さ(Ra)は、粗さ曲線からその平均線の方向に基準長さだけを抜きとったとき、この抜き取り部分の平均線の方向にx軸を、断面の縦倍率の方向にy軸を取り、粗さ曲線をy=f(x)で表したときに求められる。
nx≒ny>nzのネガティブCプレート、
nx≒ny<nzのポジティブCプレート、
nx≠ny≠nzのポジティブOプレートおよびネガティブOプレート
R0 =(nx−ny)×d (9)
R50=(nx−ny’)×d/cos(φ) (10)
(nx+ny+nz)/3=n0 (11)
ここで、
φ=sin−1 〔sin(50°)/n0〕
ny’=ny×nz/〔ny 2×sin2(φ)+nz 2×cos2(φ)〕1/2
上記の位相差フィルム及び偏光フィルムは、基材を有していてもよいし、有していなくてもよい。位相差フィルム1及び1’に、光学異方性フィルムが位相差フィルムである、本発明の光学異方性フィルム及び積層体を用いることができ、偏光フィルム2に、光学異方性フィルムが偏光フィルムである、本発明の光学異方性フィルム及び積層体を用いることができる。
組成を表1に示す。サンエバーSE−610(日産化学工業株式会社製)(配向性ポリマー)にγ−ブチロラクトン(GBL)および酢酸ブチルを加えた溶液に、添加剤LR9000を添加して配向膜形成用組成物(1)を調整した。
表1におけるLR9000は、BASFジャパン社製のLaromer(登録商標)LR−9000を表す。
光学異方層形成用組成物(1)~(6)の組成を表2に示す、各成分を混合し、得られた溶液を80℃で1時間攪拌した後、室温まで冷却して調製した。液晶化合物(X−1)は、特開2010−1284号公報に記載の方法で製造した。
シクロオレフィンポリマーフィルム(Arton(商標登録)、JSR株式会社製)の表面を、コロナ処理装置(AGF−B10、春日電機株式会社製)を用いて出力0.3kW、処理速度3m/分の条件で1回処理した。
コロナ処理を施した表面に、配向膜形成用組成物(1)を塗布し、乾燥して、厚さ60nmの配向膜を作成した。得られた配向膜の表面に、光異方性層形成用組成物(1)を、バーコーターを用いて塗布し、105℃に加熱し、未重合フィルムを配向膜上に形成した。室温まで冷却した後、ユニキュア(VB—15201BY−A、ウシオ電機株式会社製)を用いて、紫外線を、波長365nmにおいて40mW/cm2の照度で30秒間照射し、積層体(1)を得た。
実施例1における、光学異方層形成用組成物(1)を光学異方層形成用組成物(2)、光学異方層形成用組成物(3)、光学異方層形成用組成物(4)、光学異方層形成用組成物(5)又は光学異方性層形成用組成物(6)とした以外は、実施例1と同様の条件で実施し、積層体(2)~(5)を得た。
スガ試験機株式会社製 ヘイズメーター(型式HZ−2)を用いて、ダブルビーム法で、積層体(1)~(6)のヘイズ値を測定した。結果を表3に示す。
積層体(1)~(6)に含まれる重合後の重合性液晶化合物の配向方向を測定機(KOBRA−WR、王子計測機器社製)により測定した。サンプルへの光の入射角を変えて測定し、液晶が垂直配向しているかどうか確認した。
光学異方性フィルムの表面の算術平均粗さを、レーザー顕微鏡(LEXT、オリンパス株式会社製)を用いて算出した(対物レンズ:100倍)。結果を表3に示す。
JIS−K5600に則り、コーテック株式会社製クロスカットガイドIシリーズ(CCI−1、1mm間隔、25マス用)を用いて、積層体(1)~(6)の、配向膜と光学異方性フィルムとの剥離耐性を評価した。剥離試験後、剥離せずに保持された配向膜と光学異方性フィルムとの積層体の残存数をカウントした結果を表3に示す。
2、2’:偏光フィルム
3、3’:接着剤層
4a、4b、4c、4d、4e、4、4’:偏光板
5、5’:接着層
6:液晶パネル
10a、10b:液晶表示装置
Claims (15)
- 重合性液晶化合物、光重合開始剤及び沸点が120~200℃でかつ蒸気圧が0.7kPa以下であるエステル溶剤を含む光学異方層形成用組成物。
- エステル溶剤が、酢酸2−メトキシエチル、酢酸2−エトキシエチル及びアセト酢酸エチルからなる群から選ばれる少なくとも1種である請求項1記載の光学異方層形成用組成物。
- 光学異方層形成用組成物に対するエステル溶剤の含有量が10質量%~95質量%である請求項1又は2に記載の光学異方層形成用組成物。
- さらにイソシアネート基を有する化合物を含む、請求項1~3のいずれかに記載の光学異方層形成用組成物。
- 請求項1~4のいずれかに記載の光学異方層形成用組成物を、配向膜の表面に塗布して該光学異方層形成用組成物に含まれる重合性液晶化合物を重合することにより得られる光学異方性フィルム。
- 位相差フィルムである請求項5に記載の光学異方性フィルム。
- 表面の算術平均粗さが100nm以下である請求項5又6に記載の光学異方性フィルム。
- IPS(in−plane switching)液晶表示装置用の請求項5~7のいずれかに記載の光学異方性フィルム。
- 請求項5~8のいずれかに記載の光学異方性フィルムを有する偏光板。
- 請求項5~8のいずれかに記載の光学異方性フィルムを備えた表示装置。
- 基材と、配向膜と、請求項5~8のいずれかに記載の光学異方性フィルムをこの順に有する積層体。
- 基材がポリオレフィン樹脂である請求項11に記載の積層体。
- 配向膜付基材の配向膜表面に、請求項1~4のいずれかに記載の光学異方層形成用組成物を塗布し、乾燥し、光照射する積層体の製造方法。
- 請求項11又は12に記載の積層体を有する偏光板。
- 請求項11又は12に記載の積層体を備えた表示装置。
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