WO2013021826A1 - 重合性液晶組成物、及び光学異方体の製造方法 - Google Patents

重合性液晶組成物、及び光学異方体の製造方法 Download PDF

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WO2013021826A1
WO2013021826A1 PCT/JP2012/068953 JP2012068953W WO2013021826A1 WO 2013021826 A1 WO2013021826 A1 WO 2013021826A1 JP 2012068953 W JP2012068953 W JP 2012068953W WO 2013021826 A1 WO2013021826 A1 WO 2013021826A1
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liquid crystal
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polymerizable liquid
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French (fr)
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長谷部　浩史
桑名　康弘
小谷　邦彦
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Dic株式会社
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
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    • G—PHYSICS
    • G02—OPTICS
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    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C09K2019/181—Ph-C≡C-Ph
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C09K2019/183—Ph-Ph-C≡C-Ph
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
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    • C09K2019/188—Ph-C≡C-Ph-C≡C-Ph
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    • C09K2019/2035—Ph-COO-Ph
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    • C09K2019/2078—Ph-COO-Ph-COO-Ph

Definitions

  • the present invention relates to an optical anisotropic body useful as a liquid crystal device, a display, an optical component, a colorant, a security marking, and a laser emission member, and a method for producing the same.
  • optically anisotropic bodies obtained by ultraviolet curing in a state in which a polymerizable liquid crystal material is aligned. Since such an optical anisotropic body is mainly used for polarization control applications such as a retardation film, it is required to control light scattering of the optical anisotropic body as small as possible. This is because if the light scattering is large, a part of the polarization state is lost, and the polarization state control becomes incomplete.
  • the optical anisotropic body since the light scattering increases as the thickness of the optical anisotropic body increases, the influence is serious particularly in the optical anisotropic body having a thickness of 2 ⁇ m or more.
  • Examples of the optical anisotropic body that requires a thickness of 2 ⁇ m or more include an optical low-pass filter and a reflective polarizing plate using a cholesteric liquid crystal (Patent Document 1).
  • Patent Document 1 there has been no means for effectively suppressing light scattering in such an optical film.
  • the problem to be solved by the present invention is a polymerizable liquid crystal composition that suppresses light scattering of an optical anisotropic body obtained by curing active energy rays in an aligned state of the polymerizable liquid crystal material, and an optical heterogeneity using the same.
  • the object is to provide means for suppressing light scattering of a rectangular parallelepiped.
  • polymer impurities having a molecular weight of about 5,000 or more and oligomer impurities having a molecular weight of about 2 to 4 in the polymerizable liquid crystal composition induce light scattering, and the size that induces light scattering has a large molecular weight. I found that it grows.
  • the magnitude of the influence of tri- and tetrameric impurities causing light scattering is about 5.3 times that of dimeric impurities. That is, the inventors have found that the light scattering magnitude when the tri- and tetrameric impurities are 100 ppm is almost equal to the light scattering magnitude when the dimer impurity is 530 ppm. In addition, the inventors have also found that oligomer impurities having a cyano group are about 47 times larger in the influence of causing light scattering than oligomer impurities not having a cyano group.
  • the present invention relates to the oligomer impurity in the polymerizable liquid crystal composition having a concentration of a cyano group-containing tri- to tetramer impurity a (ppm) and a concentration of a cyano group-containing dimer impurity b (ppm).
  • 3-4 amounts of the oligomer impurities in the polymerizable liquid crystal composition having a cyano group The concentration of the body impurity is a (ppm), the concentration of the dimer impurity having a cyano group is b (ppm), the concentration of the trimer to tetramer impurity having no cyano group is c (ppm), and the cyano group is present.
  • the concentration of the dimer impurities not to be used is d (ppm) and the thickness of the obtained optical anisotropic body is e ( ⁇ m)
  • the formula (I) x [(a + 0.19b) +0.0215 (c + 0.19d)] / e (I)
  • the production method is characterized in that the polymerizable liquid crystal composition controlled so that the x value represented by the formula is 150 or less is used.
  • the polymerizable liquid crystal composition and the method for producing an optical anisotropic body of the present invention since light scattering is reduced, depolarization is suppressed, and an optical anisotropic body having good polarization control performance can be obtained. .
  • the concentration of oligomer impurities in the polymerizable liquid crystal composition can be measured with a GPC (gel permeation chromatograph) apparatus.
  • the concentration of the cyano group-containing trimer to tetramer impurity is a (ppm)
  • the concentration of the cyano group-containing dimer impurity is b (ppm)
  • the concentration of the tri- to tetramer impurity having a cyano group is a (ppm)
  • the concentration of the dimer impurity having a cyano group is b (ppm)
  • no cyano group is contained.
  • the concentration of tetramer impurities is c (ppm)
  • the concentration of dimer impurities not having a cyano group is d (ppm)
  • the thickness of the optical anisotropic body obtained by curing the polymerizable liquid crystal composition is e.
  • the formula (I) x [(a + 0.19b) +0.0215 (c + 0.19d)] / e (I) It is preferable to manage so that the x value represented by the formula is 150 or less, more preferably 110 or less, and particularly preferably 80 or less. However, if these Xa values and x values are to be managed to be unnecessarily low, the purification cost and time in the production of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition will be increased. It is necessary to adjust the control value.
  • the concentration of the oligomeric impurities can be determined by using a sufficient amount of a polymerization inhibitor in the synthesis of the polymerizable liquid crystal compound to be used. It can be effectively reduced by the activated carbon treatment.
  • the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition can be applied to either a rod shape or a disk shape.
  • the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition can be used without particular limitation as long as it is recognized as a polymerizable liquid crystal compound in this technical field.
  • a compound having only one polymerizable functional group in the molecule is preferable because it is easy to produce a compound containing a low temperature around room temperature as the liquid crystal temperature range of the composition.
  • Examples of such compounds include, for example, Handbook of Liquid Crystals (D. Demus, JW Goodby, GW Gray, HW Spies, V. Vill, edited by Wiley-VCH, 1998). , Quarterly Chemical Review No.
  • a rod-like polymerizable liquid crystal compound having a polymerizable functional group such as a vinyl group, an acryloyl group or a (meth) acryloyl group, or a maleimide as described in JP-A Nos. 2004-2373 and 2004-99446 Examples thereof include a rod-like polymerizable liquid crystal compound having a group.
  • Examples of the polymerizable functional group include a vinyl group, an acryloyl group, a (meth) acryloyl group, and a maleimide group. From the viewpoint of productivity, an acryloyl group and a (meth) acryloyl group are preferable.
  • liquid crystal compound having only one polymerizable functional group is preferably a compound represented by the following general formula (a).
  • Z 3 represents a hydrogen atom, a halogen atom, a cyano group or a hydrocarbon group having 1 to 20 carbon atoms
  • Z 4 represents a hydrogen atom or a methyl group
  • W 3 represents a single bond, —O—, -COO- or -OCO-
  • v represents an integer of 0 to 18
  • u represents 0 or 1
  • D E and F are each independently a 1,4-phenylene group or a non-adjacent CH group.
  • R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, or a carbamoyl group.
  • a cyano group, a nitro group, and a halogen atom and when these groups are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, they are all unsubstituted, When these groups are a carboxyl group or a carbamoyl group, the terminal hydrogen atom may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • R preferably represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a cyano group. Since the compound having a cyano group as R is greatly affected by oligomer impurities, its concentration control is important.
  • liquid crystal compounds can be used alone or in combination of two or more.
  • the content of the compound represented by the general formula (a) is preferably 5% to 70%, more preferably 7% to 60%, and particularly preferably 9% to 50%.
  • a liquid crystal compound having two polymerizable functional groups is useful from the viewpoint of ensuring the mechanical strength of a film obtained by curing.
  • examples of such compounds having two polymerizable functional groups include, for example, Handbook of Liquid Crystals (D. Demus, JW Goodby, GW Gray, HW Spiss, V. Vill, edited by Wiley. -Published by VCH, 1998), Quarterly Chemical Review No. 22, Liquid Crystal Chemistry (edited by the Chemical Society of Japan, 1994), or Japanese Patent Laid-Open Nos.
  • 1,4-phenylene group 1,4-cyclohex A rod-like polymerizable liquid crystal compound having a rigid site called mesogen in which a plurality of structures such as a len group are connected, and a polymerizable functional group such as a vinyl group, an acryloyl group, and a (meth) acryloyl group, or JP-A-2004-2373, A rod-like polymerizable liquid crystal compound having a maleimide group as described in JP-A-2004-99446 And the like.
  • Examples of the polymerizable functional group include a vinyl group, an acryloyl group, a (meth) acryloyl group, and a maleimide group. From the viewpoint of productivity, an acryloyl group and a (meth) acryloyl group are preferable.
  • liquid crystal compound having two polymerizable functional groups is preferably a compound represented by the following general formula (b).
  • Z 5 and Z 6 each independently represent a hydrogen atom or a methyl group
  • G, H and I each independently represent a 1,4-phenylene group and a non-adjacent CH group substituted with nitrogen.
  • a 1,4-phenylene group present in the formula may be substituted with one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms;
  • W 1 and W 2 each independently represent a single bond, —O—, —COO— or —OCO—
  • Y 1 and Y 2 each independently represent a single bond, — COO-, -OCO-, -CH 2 CH
  • R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, a carbamoyl group, cyano.
  • R is preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a cyano group.
  • liquid crystal compounds can be used alone or in combination of two or more.
  • the content of the compound represented by the general formula (b) is preferably 5% to 90%, more preferably 10% to * 80%, and particularly preferably 20% to 70%.
  • an additive may be contained depending on the purpose.
  • R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one hydrocarbon atom in the hydrocarbon group
  • a compound having a repeating unit represented by the above-mentioned halogen atom may be used.
  • Examples of the compound represented by the general formula (II) include polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin, and chlorinated liquid paraffin.
  • the compound which has a repeating unit represented by these is mentioned.
  • structures represented by the formulas (II-a) to (II-e) are more preferable, and structures represented by the formulas (II-a) and (II-c) are particularly preferable.
  • a copolymer obtained by copolymerizing two or more compounds having a repeating unit represented by formulas (II-a) to (II-f) is also preferable.
  • the mass average molecular weight of the compound is too small, the effect of reducing the tilt angle is poor, and if it is too large, the orientation is not stable for a long time, so there is an optimum range.
  • it is preferably 200 to 1000000, more preferably 300 to 100,000, and particularly preferably 400 to 80000.
  • the compound is preferably contained in the polymerizable liquid crystal composition in an amount of 0.01 to 5% by mass, more preferably 0.05 to 2% by mass, and 0.1 to 1% by mass. Is particularly preferred.
  • a chiral compound is added so as to exhibit a cholesteric liquid crystal phase (chiral nematic liquid crystal phase).
  • a chiral compound preferably has one or more polymerizable functional groups. Examples of such compounds include JP-A-11-193287, JP-A-2001-158788, JP-T 2006-52669, JP-A-2007-269639, JP-A-2007-269640, 2009.
  • -84178 which contains chiral saccharides such as isosorbide, isomannite, glucoside, and the like, and a rigid site such as 1,4-phenylene group and 1,4-cyclohexylene group, and a vinyl group
  • a polymerizable chiral compound having a polymerizable functional group such as an acryloyl group, a (meth) acryloyl group, or a maleimide group, a polymerizable chiral compound comprising a terpenoid derivative as described in JP-A-8-239666, NATURE VOL35, pages 467-469 (November 30, 1995) Issue), NATURE VOL392, pages 476-479 (issued on April 2, 1998), or the like, or a polymerizable chiral compound comprising a mesogenic group and a spacer having a chiral moiety, or JP-T-2004-504285.
  • a polymerizable chiral compound containing a binaphthyl group as described in JP-A-2007-248945 a polymerizable chiral compound containing a binaphthyl group as described in JP-A-2007-248945.
  • a chiral compound having a large helical twisting power (HTP) is preferable because the polymerizable liquid crystal composition of the present invention can be easily produced.
  • chiral compound used in the polymerizable liquid crystal composition include the following liquid crystal compounds.
  • n and n each independently represent an integer of 1 to 10
  • R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, a carbamoyl group, cyano.
  • these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, they are all unsubstituted, or one or two
  • these groups are a carboxyl group or a carbamoyl group, the terminal hydrogen atom may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • These chiral compounds can be used alone or in combination of two or more.
  • a polymerization initiator may be added to the polymerizable liquid crystal composition.
  • a polymerization initiator a well-known usual thing can be used as a photoinitiator used when performing by an active energy ray.
  • 2-hydroxy-2-methyl-1-phenylpropan-1-one (“Darocur 1173” manufactured by Merck)
  • 1-hydroxycyclohexyl phenyl ketone (“Irgacure 184” manufactured by Ciba Specialty Chemicals)
  • 1- ( 4-Isopropylphenyl) -2-hydroxy-2-methylpropan-1-one (“Darocur 1116” manufactured by Merck & Co.)
  • 2-methyl-1-[(methylthio) phenyl] -2-morpholinopropane-1 “Irgacure 907” manufactured by Ciba Specialty Chemicals).
  • Benzylmethylketal (“Irgacure 651” manufactured by Ciba Specialty Chemicals) 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone (“Irgacure 369” manufactured by Ciba Specialty Chemicals) ), 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) butan-1-one (“Irgacure 379” manufactured by Ciba Specialty Chemicals), 2 , 2-Dimethoxy-1,2-diphenylethane-1-one, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (Darocur TPO), 2,4,6-trimethylbenzoyl-diphenyl-phosphine Oxide (“Irgaku” manufactured by Ciba Specialty Chemicals) 819 "), 1,2-octanedione, 1- [4- (phenylthio)
  • the content of the photopolymerization initiator is preferably 1 to 10% by mass, particularly preferably 2 to 7% by mass. These can be used alone or in combination of two or more.
  • thermal polymerization initiator examples include methyl acetoacetate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxybenzoate, and methyl ethyl ketone peroxide.
  • Oxide 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, p-pentahydroperoxide, t-butylhydroperoxide, dicumyl peroxide, isobutyl peroxide, di (3- Methyl-3-methoxybutyl) peroxydicarbonate, organic peroxides such as 1,1-bis (t-butylperoxy) cyclohexane, 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-Dimethylvaleronitrile ), Azonitrile compounds such as 2,2′-azobis (2-methyl-N-phenylpropion-amidin) dihydrochloride, 2,2′azobis ⁇ 2-methyl-N- [1,1-bis An azoamide compound such as (hydroxymethyl) -2-hydroxyethyl] propionamide ⁇ , an alkylazo compound such as 2,2′azobis (2,4,4-trimethylpentan
  • a polymerization inhibitor to the polymerizable liquid crystal composition.
  • the polymerization inhibitor include phenol compounds, quinone compounds, amine compounds, thioether compounds, nitroso compounds, and the like.
  • phenolic compounds include p-methoxyphenol, cresol, t-butylcatechol, 3.5-di-t-butyl-4-hydroxytoluene, 2.2'-methylenebis (4-methyl-6-t-butylphenol) 2.2′-methylenebis (4-ethyl-6-tert-butylphenol), 4.4′-thiobis (3-methyl-6-tert-butylphenol), 4-methoxy-1-naphthol, 4,4′- Dialkoxy-2,2′-bi-1-naphthol, and the like.
  • quinone compounds include hydroquinone, methylhydroquinone, tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, 2,5-diphenylbenzoquinone, 2-hydroxy-1,4-naphthoquinone 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone, diphenoquinone and the like.
  • amine compounds include p-phenylenediamine, 4-aminodiphenylamine, N.I.
  • N'-diphenyl-p-phenylenediamine Ni-propyl-N'-phenyl-p-phenylenediamine, N- (1.3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N.I. N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl- ⁇ -naphthylamine, 4.4′-dicumyl-diphenylamine, 4.4′-dioctyl-diphenylamine and the like.
  • thioether compounds include phenothiazine and distearyl thiodipropionate.
  • nitroso compounds include N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, ⁇ -nitroso- ⁇ -naphthol, and the like, N, N-dimethyl p-nitrosoaniline, p-nitrosodiphenylamine, p-nitronedimethylamine, p-nitrone-N, N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-N-n-butyl- 4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitro
  • surfactants that can be included include alkyl carboxylates, alkyl phosphates, alkyl sulfonates, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, polyoxyethylene derivatives, fluoro Examples thereof include alkylethylene oxide derivatives, polyethylene glycol derivatives, alkylammonium salts, fluoroalkylammonium salts, silicone derivatives and the like, and fluorine-containing surfactants and silicone derivatives are particularly preferable.
  • MEGAFAC F-110 “MEGAFACCF-113”, “MEGAFAC F-120”, “MEGAFAC F-812”, “MEGAFAC F-142D”, “MEGAFAC F-144D”, “MEGAFAC F-” 150 ”,“ MEGAFAC F-171 ”,“ MEGAFACF-173 ”,“ MEGAFAC F-177 ”,“ MEGAFAC F-183 ”,“ MEGAFAC F-195 ”,“ MEGAFAC F-824 ”,“ MEGAFAC F-833 ” , “MEGAFAC F-114”, “MEGAFAC F-410”, “MEGAFAC F-493”, “MEGAFAC F-494”, “MEGAFAC F-443”, “MEGAFAC F-444”, “MEGAFAC F-445”, “ME “GAFAC F-446”, “MEGAFAC F-470”, “MEGAFAC F-471”, “MEGAFAC F-474”, “MEGAFAC F-475”, “MEGAFAC
  • the preferred addition amount of the surfactant varies depending on components other than the surfactant contained in the polymerizable liquid crystal composition, the use temperature, etc., but is contained in the polymerizable liquid crystal composition in an amount of 0.01 to 1% by mass.
  • the content is preferably 0.02 to 0.5% by mass, more preferably 0.03 to 0.1% by mass. When the content is lower than 0.01% by mass, it is difficult to obtain the effect of reducing film thickness unevenness.
  • the total content of the horizontal alignment additive having a repeating unit represented by the general formula (I) and the content of the surfactant is preferably 0.02 to 0.5% by mass, and 0.05 to 0
  • the content is more preferably 4% by mass, and particularly preferably 0.1 to 0.2% by mass.
  • the polymerizable liquid crystal composition may contain other additives such as thixotropic agents, surfactants, ultraviolet absorbers, infrared absorbers, antioxidants, surface treatment agents, and the like. Can be added to such an extent that it does not significantly decrease.
  • the optical anisotropic body of the present invention can be produced by forming a polymerizable liquid crystal composition with controlled oligomer purity on a substrate by a method such as coating, and then curing.
  • the base material used for the optical anisotropic body of the present invention is a base material usually used for a liquid crystal device, a display, an optical component or an optical film, and when dried after application of the polymerizable liquid crystal composition of the present invention, or
  • the material is not particularly limited as long as it is a material having heat resistance capable of withstanding heating at the time of manufacturing a liquid crystal device.
  • Examples of such a substrate include organic materials such as a glass substrate, a metal substrate, a ceramic substrate, and a plastic substrate.
  • the substrate is an organic material
  • cellulose derivatives, polyolefins, polyesters, polyolefins, polycarbonates, polyacrylates, polyarylates, polyether sulfones, polyimides, polyphenylene sulfides, polyphenylene ethers, nylons, polystyrenes, and the like can be given.
  • plastic substrates such as polyester, polystyrene, polyolefin, cellulose derivatives, polyarylate, and polycarbonate are preferable.
  • surface treatment of these substrates may be performed.
  • the surface treatment include ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like.
  • an organic thin film, an inorganic oxide thin film, a metal thin film, etc. are provided on the substrate surface by a method such as vapor deposition, or in order to add an optical added value.
  • the material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a color filter, or the like. Among these, a pickup lens, a retardation film, a light diffusion film, and a color filter that have higher added value are preferable.
  • the substrate is usually subjected to an alignment treatment or an alignment film so that the polymerizable liquid crystal composition is aligned when the polymerizable liquid crystal composition of the present invention is applied and dried.
  • the alignment treatment include stretching treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, and the like.
  • the alignment film a known and conventional alignment film is used.
  • alignment films include polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, epoxy acrylate resin, acrylic resin, coumarin compound, chalcone.
  • the compound examples include compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds, and arylethene compounds.
  • the compound subjected to the alignment treatment by rubbing is preferably an alignment treatment or a compound in which crystallization of the material is promoted by inserting a heating step after the alignment treatment.
  • Applicable methods such as applicator method, bar coating method, spin coating method, gravure printing method, flexographic printing method, ink jet method, die coating method, cap coating method, dipping, etc. are known as methods for applying the polymerizable liquid crystal material to the substrate. Conventional methods can be performed. It is preferable to apply a polymerizable liquid crystal composition diluted with a solvent.
  • the solvent to be used may be any solvent that does not dissolve the substrate or the alignment film formed on the substrate when applied on the substrate.
  • a solvent that favorably dissolves the polymerizable cholesteric liquid crystal composition of the present invention is preferable.
  • solvents examples include aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate, and butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene
  • ester solvents such as methyl acetate, ethyl acetate, propyl acetate, and butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • Ketone solvents such as tetrahydrofuran, ether solvents such as tetrahydrofuran, 1,2-dimethoxyethane, anisole, amide solvents such as N, N-dimethylformamide, N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, diethylene glycol Examples include monomethyl ether acetate, ⁇ -butyrolactone, chlorobenzene and the like. These can be used alone or in combination of two or more.
  • the ratio of the solvent is not particularly limited as long as the polymerizable liquid crystal composition used in the present invention is usually applied by coating, so long as the applied state is not significantly impaired, but the solid content of the polymerizable liquid crystal composition and the solvent
  • the ratio is preferably 0.1: 99.9 to 80:20, and more preferably 1:99 to 60:40 in view of coating properties.
  • the polymerization operation of the polymerizable liquid crystal composition of the present invention is preferably performed by generally irradiating active energy rays in a state of being oriented in a desired state after removing the solvent in the polymerizable liquid crystal composition by drying or the like.
  • active energy rays include ultraviolet rays and electron beams. From the simplicity of the apparatus, it is preferable to use ultraviolet rays as the active energy ray.
  • ultraviolet light irradiation specifically, it is preferable to irradiate ultraviolet light having a wavelength of 390 nm or less, and most preferable to irradiate light having a wavelength of 250 to 370 nm.
  • the polymerizable liquid crystal composition causes decomposition or the like due to ultraviolet light of 390 nm or less, it may be preferable to perform polymerization treatment with ultraviolet light of 390 nm or more.
  • This light is preferably diffused light and unpolarized light.
  • the intensity of the ultraviolet light is preferably 1 ⁇ 100mW / cm 2, more preferably 2 ⁇ 50mW / cm 2, particularly preferably 5 ⁇ 30mW / cm 2.
  • the optical anisotropic body can be heat-treated.
  • the heating temperature is preferably within a range not exceeding the glass transition point of the base material when an organic material is used as the base material.
  • Example 1 15.18% polymerizable liquid crystal compound represented by formula (A-1), 6.50% polymerizable liquid crystal compound represented by formula (A-2), 23.85% polymerizable liquid crystal compound represented by formula (B-1) 32.52% of a polymerizable liquid crystal compound represented by the formula (B-2), 7.01% of a polymerizable chiral compound represented by the formula (C-1), 8.67% of a polymerizable liquid crystal compound represented by the formula (D-1) %, Liquid crystal compound represented by formula (E-1) 3.25%, photopolymerization initiator represented by formula (F-1) 2.17%, photopolymerization initiator represented by formula (F-2) 0.44 parts Then, 0.44 part of p-methoxyphenol (E-1) was mixed to obtain a polymerizable cholesteric liquid crystal composition (1).
  • the oligomer impurities contained in this polymerizable cholesteric liquid crystal composition were analyzed using GPC and NMR. As a result, the total of ternary tetramer impurities (I-1) and (I-2) having a cyano group was 182 ppm, The total amount of dimer impurities (I-3) and (I-4) having a cyano group is 1182 ppm, and the total amount of tri to tetramer impurities (I-5) to (I-8) having no cyano group is The total amount of dimer impurities (I-9) to (I-12) having no cyano group was 4385 ppm. The Xa value calculated from the formula (Ia) in this polymerizable cholesteric liquid crystal composition (1) was 434.
  • R 1 and R 2 represents a hydrogen atom, the other represents the formula (I-1b), and m1 represents 3 or 4)
  • R 3 and R 4 represents a hydrogen atom, the other represents the formula (I-2b), and m2 represents 3 or 4)
  • one of R 9 and R 10 represents a hydrogen atom, the other represents the formula (I-5b), and m3 represents 3 or 4)
  • R 11 and R 12 represents a hydrogen atom, the other represents the formula (I-6b), and m4 represents 3 or 4)
  • R 13 and R 14 represents a hydrogen atom, the other represents the formula (I-7b), and m5 represents 3 or 4)
  • R 15 and R 16 represents a hydrogen atom, the other represents the formula (I-8b), and m6 represents 3 or 4)
  • the polymerizable cholesteric liquid crystal composition (A) of the present invention was prepared by adding 0.10% of polypropylene having a weight average molecular weight of 1650 as a horizontal alignment additive to the prepared polymerizable cholesteric liquid crystal composition (1).
  • 30% toluene and 30% cyclohexanone were added to prepare a solution of the polymerizable liquid crystal composition (1 ′).
  • the polyimide solution for alignment film was applied to a glass substrate having a thickness of 0.7 mm using a spin coating method, dried at 100 ° C. for 10 minutes, and then baked at 200 ° C. for 60 minutes to obtain a coating film. .
  • the obtained coating film was rubbed to obtain a cholesteric reflective film substrate of the present invention.
  • the rubbing treatment was performed using a commercially available rubbing apparatus.
  • a solution of the polymerizable liquid crystal composition (1 ′) was applied to the rubbed substrate by a spin coating method and dried at 65 ° C. for 3 minutes.
  • the obtained coating film was placed on a hot plate at 60 ° C., and a 15 mW / cm 2 high-pressure mercury lamp adjusted so that ultraviolet light (UV light) of only around 365 nm was obtained with a bandpass filter. Irradiated with UV light for 10 seconds at intensity.
  • the bandpass filter was removed, and the optical anisotropic body (cholesteric reflective film) of the present invention was obtained by irradiating with UV light at an intensity of 70 mW / cm 2 for 20 seconds.
  • the film thickness of the obtained cholesteric reflective film was 5.5 ⁇ m. Moreover, it was 4.6% when the haze of the film was measured.
  • the x value calculated from formula (I) was 79.
  • Example 1 In Example 1, the experiment was performed in the same manner as in Example 1 except that the polymerizable liquid crystal compound was replaced with a compound of a lot having a different purification method. The results are shown in Table 1.
  • Example 1 (Comparative Examples 1 to 7)
  • the experiment was performed in the same manner as in Example 1 except that the polymerizable liquid crystal compound was replaced with a compound of a lot having a different purification method.
  • the results are shown in Table 1.
  • the polymerizable liquid crystal composition of the present invention having an Xa value of 825 or less has a haze of an optical anisotropic body obtained by using this of 10% or less, and can suppress light scattering.
  • the optical anisotropic body obtained by the method of the present invention having an x value of 150 or less has a haze of 10% or less, and light scattering is suppressed.

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