TW201319226A - Polymeric liquid crystal composition, optically anisotropic body and method for preparing the same - Google Patents

Abstract

The problem to be solved by the present invention is to provide a polymeric liquid crystal composition, which can inhibit the light scattering of the optically anisotropic body obtained by curing the polymeric liquid crystal material in the condition of alignment by active energy ray. The present invention is to provide a polymeric liquid crystal composition which is used for a method for preparing an optically anisotropic body by curing the polymeric liquid crystal material in the condition of alignment by active energy ray, in which when the content of trimer to tetramer impurities having cyano group is a(ppm), the content of dimer impurities having cyano group is b(ppm), the content of trimer to tetramer impurities without cyano group is c(ppm), and the content of dimer impurities without cyano group is d(ppm), Xa value represented by the expression (Ia) can be controlled as being less than 825. Xa=(a+0.19b)+0.0215(c+0.19d) (Ia)

Description

Polymerizable liquid crystal composition, optical anisotropic body, and method of producing the same

The present invention relates to an optical anisotropic body useful as a liquid crystal element, a display, an optical component, a colorant, a security mark, and a member for laser light emission, and a method for producing the same.

Many optical anisotropic bodies obtained by curing a polymerizable liquid crystal material in a state of being aligned with ultraviolet rays have been studied. Such an optical anisotropic body is mainly used for polarization control applications such as a retardation film. Therefore, it is required to suppress light scattering of an optical anisotropic body as small as possible. If the light scattering is large, the polarization state is locally lost, and the polarization state control is incomplete.

Further, since the thickness of the optical anisotropic body is thicker, the light scattering is larger, particularly in the case of an optical anisotropic body having a thickness of 2 μm or more, which has a very large influence. An optical anisotropic body having a thickness of 2 μm or more is required, and examples thereof include an optical low-pass filter or a reflective polarizing plate using cholesteric liquid crystal (Patent Document 1). However, in such an optical film, there is no means for effectively suppressing light scattering.

Patent Document 1 Japanese Patent No. 3592383

Patent Document 2 Japanese Patent No. 3828158

An object of the present invention is to provide a polymerizable liquid crystal composition capable of suppressing light scattering of an optical anisotropic body obtained by curing an active energy ray in a state in which a polymerizable liquid crystal material is aligned, and an optical using the same Light scattering suppression means for anisotropic bodies.

As a result of intensive investigation, it has been found that polymer impurities having a molecular weight of about 5,000 or more or oligomer impurities having a molecular weight of about 2 to 4 in a polymerizable liquid crystal composition cause light scattering, and the larger the molecular weight, the size of light scattering. The bigger it is.

Further, it has been found that these impurities can be removed by column chromatography, activated carbon adsorption, and molecular distillation, and removal of polymer impurities is much easier than removal of oligomer impurities. Therefore, when the concentration of the oligomer impurities is controlled to be equal to or less than a certain value, it can be in a state in which the influence of light scattering due to the polymer concentration can be ignored. It has also been found that in order to reduce light scattering of the optical anisotropic body obtained by hardening the polymerizable liquid crystal composition, it is necessary to manage the polymer and oligomer impurities causing light scattering, but regarding the management, the oligomer concentration can also be represented. management.

Further, it was found that the influence of the 3~4 polymer impurity on the light scattering was about 5.3 times that of the 2-mer impurity. That is, it was found that the light scattering amount when containing 100 ppm of the 3~4 polymer was about the same as the light scattering amount when the diol impurity containing 530 ppm was contained. Further, it has been found that the SiO group-containing oligomer impurity has a size of about 47 times larger than that of the siloxane-free oligomer impurity.

That is, the present invention provides a polymerizable liquid crystal composition characterized in that, in the oligomer in the polymerizable liquid crystal composition, when the concentration of the 3 to 4 polymer impurity having a cyano group is a (ppm), When the concentration of the cyano 2-polymer impurity is b (ppm), the concentration of the 3~4 polymer impurity having no cyano group is c (ppm), and the concentration of the 2-polymer impurity having no cyano group is d (ppm), The Xa value represented by the formula (Ia) is controlled to be 825 or less; Xa=(a+0.19b)+0.0215(c+0.19d) (Ia)

Further, a method for producing an optical anisotropic body by curing an active energy ray in a state in which a polymerizable liquid crystal material is aligned in an aligned state is provided, which is characterized in that the following polymerizable liquid crystal composition is used: The concentration of the 3~4 polymer impurity is a (ppm), the concentration of the 2 polymer impurity having a cyano group is b (ppm), and the concentration of the 3~4 polymer impurity having no cyano group is c (ppm), When the concentration of the dimer impurity having no cyano group is d (ppm) and the thickness of the optical anisotropic body obtained by curing the polymerizable liquid crystal composition is e (μm), the value of x represented by the formula (1) Control is below 150

x = [(a + 0.19b) + 0.0215 (c + 0.19d)] / e (I).

According to the method for producing a polymerizable liquid crystal composition and an optical anisotropic body of the present invention, an optical anisotropic body having reduced distortion of light scattering and excellent polarization control performance can be obtained.

The concentration of the oligomer impurities in the polymerizable liquid crystal composition can be measured by a GPC (gel permeation chromatography) apparatus.

When the concentration of the 3~4 polymer impurity having a cyano group in the polymerizable liquid crystal composition is a (ppm), the concentration of the second polymer impurity having a cyano group is b (ppm), and the concentration of the cyano group is 3 to 4 When the concentration of the impurity is c (ppm) and the concentration of the dimer impurity having no cyano group is d (ppm), the value of Xa represented by the formula (Ia) is preferably 825 or less, and more preferably 605 or less. Below 440 is especially good.

Xa=(a+0.19b)+0.0215(c+0.19d) (Ia)

Further, when the concentration of the 3 to 4 polymer impurity having a cyano group in the polymerizable liquid crystal composition is a (ppm), the concentration of the impurity having a cyano group is b (ppm), and the ratio of the cyano group is not 3 The concentration of the ~4 polymer impurity is c (ppm), the concentration of the 2 polymer impurity having no cyano group is d (ppm), and the thickness of the optical anisotropic body obtained by curing the polymerizable liquid crystal composition is e (μm). Preferably, the value of x represented by the formula (I) is preferably 150 or less, more preferably 110 or less, and particularly preferably 80 or less.

x=[(a+0.19b)+0.0215(c+0.19d)]/e (I)

However, if the Xa value or the x value is to be managed to be low, the purification cost and time in the production of the polymerizable liquid crystal compound contained in the polymerizable composition are increased, and therefore it is necessary to adjust the management value for the purpose. . The concentration of the oligomer impurity is due to the synthesis of the polymerizable liquid crystal compound used, and a sufficient amount of the polymerization inhibiting agent is used, or the obtained polymerizable liquid crystal compound is subjected to gel permeation chromatography, alumina column chromatography or Activated carbon treatment can be effectively reduced.

Any of the polymerizable liquid crystal compounds contained in the polymerizable liquid crystal composition may be in the form of a rod or a disk.

The polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition can be used without limitation as long as it is a polymerizable liquid crystal compound known in the art. Among them, a compound having only one polymerizable functional group in the molecule is preferable because the liquid crystal temperature range of the composition is easily made to include a low temperature before and after the room temperature. Such a compound may, for example, be Handbook of Liquid Crystals (D. Demus, JW Goodby, GWGray, HWSpiess, edited by V. Vill, issued by Wiley-VCH, 1998), quarterly chemical general N0.22, liquid crystal Chemistry (edited by the Chemical Society of Japan, In the case of the Japanese Unexamined Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Hei. - a rigid portion called a mesogen, which has a structure such as a 1,4-phenylene group or a 1,4-cyclohexylene group, and a vinyl group, a propylene group, or a A rod-like polymerizable liquid crystal compound having a polymerizable functional group such as an acrylonitrile group, or a rod having a maleic imine group as described in JP-A-2004-37344 and JP-A-2004-99446 A polymerizable liquid crystal compound.

Examples of the polymerizable functional group include a vinyl group, an acrylonitrile group, a (meth) acryl fluorenyl group, and a maleimide group. From the viewpoint of productivity, an acrylonitrile group or a (meth) acrylonitrile group is used. It is better.

The liquid crystal compound having only one polymerizable functional group is specifically a compound represented by the following formula (a).

(wherein 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, and W ³ represents a single bond, -O-, -COO- or -OCO -, v represents an integer from 0 to 18, u represents 0 or 1, and D, E and F each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-substituted 1,4-phenylene group. 1,4-cyclohexylene, 1 or 2 non-adjacent CH ₂ groups substituted with an oxygen or sulfur atom, 1,4-cyclohexylene, 1,4-cyclohexenylene, present in the formula The 1,4-phenylene group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and Y ⁶ and Y ⁷ each independently represent a single bond. -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -COO-, -OCO-, -C≡C-, -CH=CH-, -CF=CF-, -(CH ₂ ) ₄ -, -CH ₂ CH ₂ CH ₂ O-, -OCH ₂ CH ₂ CH ₂ -, -CH=CHCH ₂ CH ₂ -, -CH ₂ CH ₂ CH=CH-, -CH=CHCOO-, -OCOCH=CH -, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N- or -CH=NN=CH-, at least one of Y ⁶ and Y ⁷ , representing -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, - N=N-, -CH=NN=CH- Y ⁸ represents a single bond, -O-, -COO-, -OCO- or -CH=CHCOO-).

The compound represented by the formula (a) is more preferably a compound shown below.

(wherein, l, m, and n each independently represent an integer of 1 to 10, and R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkane group; a group, an amine carbenyl group, a cyano group, a nitro group, a halogen atom, when the group is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of which may be unsubstituted or It is substituted with one or two or more halogen atoms. When the group is an alkanoyl group or an amine carbenyl group, the hydrogen atom at the terminal may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the above formula, 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. The compound having a cyano group as R has a large influence on the impurity of the oligomer, so concentration management is important.

These liquid crystal compounds may be used singly or in combination of two or more.

The content of the compound represented by the formula (a) is preferably 5% to 70%, more preferably 7% to 60%, particularly preferably 9% to 50%.

The polymerizable liquid crystal compound contained in the liquid crystal composition is a liquid crystal compound having two polymerizable functional groups, and is useful from the viewpoint of ensuring the mechanical strength of the film obtained by curing. Such a compound having two polymerizable functional groups may, for example, be Handbook of Liquid Crystals (D. Demus, JW Goodby, GWGray, HWSpiess, V. Vill, Wiley-VCH, 1998), quarterly chemistry In the case of N02, liquid crystal chemistry (edited by the Chemical Society of Japan, 1994), or Japanese Patent Laid-Open No. Hei 4-227684, JP-A-H11-80090, JP-A-11-116538, and JP-A-11- 1-4 phenyl, 1, 4, as described in JP-A-2004-125842, JP-A-2002-125842, JP-A-2002-125842 - The structure of the ring-extension and other structures is connected a rod-shaped polymerizable liquid crystal compound which is a rigid portion of a liquid crystal cell and a polymerizable functional group such as a vinyl group, an acrylonitrile group or a (meth)acryl fluorenyl group, or a special one is as disclosed in JP-A-2004-2373 A rod-shaped polymerizable liquid crystal compound having a maleic imine group described in JP-A-2004-99446.

The polymerizable functional group may, for example, be a vinyl group, an acrylonitrile group, a (meth) acryl fluorenyl group or a maleimide group, and may be an acrylonitrile group or a (meth) propylene oxime from the viewpoint of productivity. The base is good.

The liquid crystal compound having two polymerizable functional groups is specifically a compound represented by the following formula (b).

(wherein, Z ⁵ and Z ⁶ each independently represent a hydrogen atom or a methyl group, and G, H and I each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-containing 1,4- a phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a phenylene group, a 1,4-cyclohexylene group, or a non-adjacent 2 CH ₂ group substituted with an oxygen or sulfur atom. The 1,4-phenylene group present in the group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and m represents an integer of 0 to 3, ¹ and W ² each independently represent a single bond, -O-, -COO- or -OCO-, and Y ¹ and Y ² each independently represent a single bond, -COO-, -OCO-, -CH ₂ CH ₂ COO- , -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N-, -CH=NN=CH- or single The bond, at least one of Y ¹ and Y ² , represents -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, -N=N-,- CH=NN=CH-, r and s each independently represent an integer from 2 to 18, and the 1,4-phenylene group present in the formula may also be an alkyl group having 1 to 7 carbon atoms, an alkoxy group or an alkane. Substituting one or more of a fluorenyl, cyano or halogen atom).

The compound represented by the formula (b) is more preferably a compound shown below.

(wherein m and n each independently represent an integer of 1 to 10, and R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkane group; a group, an amine carbenyl group, a cyano group, a nitro group, or a halogen atom, when the group is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of them may be unsubstituted. Or substituted with one or two or more halogen atoms. When the group is an alkanoyl group or an amine carbenyl group, the hydrogen atom at the terminal may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

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.

These liquid crystal compounds may be used singly or in combination of two or more.

The content of the compound represented by the formula (b) is preferably 5% to 90%, more preferably 10% to 80%, particularly preferably 20% to 70%.

The polymerizable liquid crystal composition may contain an additive depending on the purpose. In particular, in recent years, a polymerizable liquid crystal composition is applied to a substrate or the like by a method such as application to a substrate or the like, and an optical anisotropic body is produced by irradiation with an active energy ray, so that it is formed on one substrate. In the state of the layer of the polymerizable liquid crystal composition, it is important to adjust the additive in such a manner that the desired alignment state can be obtained.

When it is homogeneous (horizontal uniaxial) alignment and cholesteric liquid crystal plane (horizontal) alignment, it is necessary to add a compound for leveling the polymerizable liquid crystal composition. Such a compound may, for example, be a compound having a repeating unit represented by the formula (II).

(wherein R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom in the hydrocarbon group may be substituted by one or more halogen atoms) .

The compound represented by the formula (II) may, for example, be polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin or chlorinated liquid paraffin.

In addition to this, it is also effective to consider a compound in which a fluorine atom is introduced from the viewpoint of suppression variation.

Among the compounds having a repeating unit represented by the formula (II), a preferred structure is, for example, a compound having a repeating unit represented by the formula (II-a) to the formula (II-f). Among them, the structure represented by the formula (II-a) to the formula (II-e) is preferable, and the structure represented by the formula (II-a) and the formula (II-c) is particularly preferable. Further, a copolymer of two or more kinds of compounds having a repeating unit represented by the formula (II-a) to the formula (II-f) may be copolymerized. In this case, a copolymer having the formula (II-a) and the formula (II-b), a copolymer having the formula (II-a) and the formula (II-c), and having the formula (II-a) are preferred. And a copolymer of the formula (II-f), and a copolymer of the formula (II-a), the formula (II-b) and the formula (II-f), particularly preferably having the formula (II-a) and the formula (II) a copolymer of II-b) and a copolymer of the formula (II-a), the formula (II-b) and the formula (II-f).

If the mass average molecular weight of the compound is too small, the effect of reducing the tilt angle is not good, and if it is too large, the alignment will be unstable for a long period of time, so it must exist in an optimum range. Specifically, 200 to 1000000 is preferred, 300 to 100000 is preferred, and particularly preferred is 400 to 80,000.

Further, the polymerizable liquid crystal composition preferably contains 0.01 to 5% by mass of the compound, more preferably 0.05 to 2% by mass, even more preferably 0.1 to 1% by mass.

When it is a helical alignment, a chiral compound is added in such a manner as to exhibit a cholesteric liquid crystal phase (optical nematic liquid crystal). Such a compound, for example, JP-A-H11-193287, JP-A-2001-158788, JP-A-2006-52669, JP-A-2007-269639, JP-A-2007-269640, 2009- a chiral saccharide containing isosorbide, isomannide, or glucoside as described in the publication No. 84178, and having a rigid portion such as a 1,4-phenylene group or a 1,4-cyclohexylene group. A polymerizable chiral compound having a polymerizable functional group such as a vinyl group, an acrylonitrile group, a (meth) acryl fluorenyl group, or a maleimine group, and a oxime described in JP-A-H08-239666 Polymeric chiral compound composed of a derivative, NATURE VOL35, pages 467-469 (issued on November 30, 1995), NATURE VOL 392476-479 (issued on April 2, 1998), etc. A polymerizable chiral compound containing a spacer of a chiral moiety, or a polymerizable chiral compound containing a naphthyl group described in JP-A-2007-504285, JP-A-2007-248945 . Among them, a chiral compound having a large helical twisting power (HTP) is preferred as the polymerizable liquid crystal composition of the invention.

The chiral compound used for the polymerizable liquid crystal composition may, for example, be a liquid crystal compound as shown below.

(wherein m and n each independently represent an integer of 1 to 10, and R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylene group, an amine carbaryl group, The cyano group, the nitro group and the halogen atom may be unsubstituted or one or two or more when the group is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. The halogen atom is substituted. When the group is an alkanoyl group or an amine carbenyl group, the terminal hydrogen atom may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

These chiral compounds may be used singly or in combination of two or more.

A polymerization initiator may also be added to the polymerizable liquid crystal composition. As the polymerization initiator, a known photopolymerization initiator which is used when it is carried out by an active energy ray can be used. For example, 2-hydroxy-2-methyl-1-phenylpropan-1-one ("Darocur 1173" manufactured by Merck Co., Ltd.) and 1-hydroxycyclohexyl phenyl ketone (Irgacure 184, manufactured by Ciba Specialty Chemicals Co., Ltd.) "), 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one "Darocur 1116" manufactured by Merck Co., Ltd., 2-methyl-1-[(methylthio) Phenyl]-2- Porphyrin propane-1 ("Irgacure 651" manufactured by Ciba Specialty Chemicals Co., Ltd.), 2-benzyl-2-dimethylamino-1-(4- Phenylphenyl)-butanone ("Irgacure 369", manufactured by Ciba Specialty Chemicals Co., Ltd.), 2-methyl-1-[(methylthio)phenyl]-2- Porphyrin propane-1 ("Irgacure 907" manufactured by Ciba Specialty Chemicals Co., Ltd.), benzyl formaldehyde ("Irgacure 651" manufactured by Ciba Specialty Chemicals Co., Ltd.), benzyl-2-dimethylamino-1-(4) - Phenylphenyl)-butanone ("Irgacure 369", manufactured by Ciba Specialty Chemicals Co., Ltd.), 2-dimethylamino-2-(4-methylbenzyl)-1-(4- Physo-4-yl-phenyl)butan-1-one ("Irgacure 379" manufactured by Ciba Specialty Chemicals Co., Ltd.), 2,2-dimethoxy-1,2-diphenylethane-1- Ketone, bis(2,4,6-trimethylbenzylidene)-phenylphosphine oxide (DarocurTPO), 2,4,6-trimethylbenzimidyl-diphenyl-phosphine oxide (Ciba "Irgacure 819" manufactured by Specialty Chemicals Co., Ltd., 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoguanidinopurine)]ethane (Ciba "Irgacure OXE01" manufactured by Specialty Chemicals Co., Ltd., 1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-, 1-(O-ethenyl)肟) ("Irgacure OXE02" manufactured by Ciba Specialty Chemicals Co., Ltd.); 2,4-diethyl thioxanthone (Kayacure DETX manufactured by Nippon Kayaku Co., Ltd.) and p-dimethylaminobenzoic acid ethyl ester ( A mixture of "Kayacure EPA" manufactured by Nippon Kayaku Co., Ltd., a mixture of isopropyl thioxanthone ("Quantacure ITX" manufactured by Ward Blenkinsop Co., Ltd.) and ethyl p-dimethylaminobenzoate ("Kayacure EPA" manufactured by Nippon Kayaku Co., Ltd.) , fluorenylphosphine oxide ("Lucirin TPO" manufactured by BASF Corporation). The content of the photopolymerization initiator is preferably from 1 to 10% by mass, particularly preferably from 2 to 7% by mass. These may be used singly or in combination of two or more.

Further, a thermal polymerization initiator may be added. As the thermal polymerization initiator, for example, methyl acetate peroxide, cumene hydroperoxide, benzhydryl peroxide, bis(4-tert-butylcyclohexyl)peroxydicarbonate can be used. , tertiary butyl peroxybenzoate, methyl ethyl ketone peroxide, 1,1-bis (tri-hexyl peroxy) 3,3,5-trimethylcyclohexane, p-pentyl hydroperoxide, three Grade butyl hydroperoxide, dicumyl peroxide, isobutyl peroxide, bis(3-methyl-3-methoxybutyl)peroxycarbonate, 1,1-double (third stage An organic peroxide such as butyl peroxy)cyclohexane; an azonitrile compound such as 2,2'-azobisisobutyronitrile or 2,2'-azobis(2,4-dimethylvaleronitrile) 2,2'-azobis(2-methyl-N-phenylpropane-indole) dihydrochloride and other azo compounds, 2,2'-azobis{2-methyl-N-[ 1,1-bis(hydroxymethyl)-2-hydroxyethyl]propanamine} and other azoamine compounds, 2,2'-azobis(2,4,4-trimethylpentane), etc. Alkyl azo compounds and the like. The content of the thermal polymerization initiator is preferably from 1 to 10% by mass, particularly preferably from 2 to 6% by mass. These may be used singly or in combination of two or more.

Further, it is preferred to add a polymerization inhibiting agent to the polymerizable liquid crystal composition. Examples of the polymerization inhibiting agent include a phenol compound, an anthraquinone compound, an amine compound, a thioether compound, and a nitroso compound.

Examples of the phenol compound include p-methoxyphenol, cresol, tertiary butyl catechol, 3,5-di-tertiary butyl-4-hydroxytoluene, and 2,2'-methylenebis ( 4-methyl-6-tertiary butyl phenol), 2,2'-methylenebis(4-ethyl-6-tertiary butylphenol), 4,4'-thiobis(3-methyl Base-6-tertiary butyl phenol), 4-methoxy-1-naphthol, 4,4'-dialkoxy-2,2'-di-1-naphthol, and the like.

The lanthanoid compound may, for example, be hydroquinone, methylhydroquinone, tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone or 2,5-diphenylbenzene. Anthracene, 2-hydroxy-1,4-naphthoquinone, 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthracene, biphenyl fluorene, and the like.

The amine compound may, for example, be p-phenylenediamine, 4-aminodiphenylamine, N,N'-diphenyl-p-phenylenediamine or N-isopropyl-N'-phenyl-pair. Phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N,N'-di-2-naphthyl-p-phenylenediamine, two Phenylamine, N-phenyl-β-naphthylamine, 4,4'-bisisophenylpropyl-diphenylamine, 4,4'-dioctyl-diphenylamine, and the like.

a thioether compound, for example, a thiophene (phenothiazine), di(octadecyl) thiodipropionate, and the like.

The nitroso compound may, for example, be N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, P-nitrosodiphenylamine, α-nitroso-β-naphthol, N,N-dimethyl-p-nitroanilide, p-nitrosodiphenylamine, p-nitrosodimethylamine , p-nitroso-N,N-diethylamine, N-nitrosethanolamine, N-nitroso-n-butylamine, N-nitroso-N-n-butyl-4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitroso Porphyrin, N-nitroso-N-phenylhydroxylamine ammonium salt, nitrosobenzene, 2,4,6-tri-tertiary butyl nitrosobenzene, N-nitroso-N-methyl- p-Toluenesulfonamide, N-nitroso-N-ethylcarbamate, N-nitroso-N-n-propyl carbamate, 1-nitroso-2-naphthol, 2- Nitroso-1-naphthol, sodium 1-nitroso-2-naphthol-3,6-sulfonate, sodium 2-nitroso-1-naphthol-4-sulfonate, 2-nitroso 5-5-methylamine phenol hydrochloride, 2-nitroso-5-methylamine phenol hydrochloride, and the like.

Further, in the polymerizable liquid crystal composition, it is preferred to add a surfactant in order to ensure the leveling property of the coating film. The surfactant which may be contained may, for example, be an alkyl carboxylate, an alkyl phosphate, an alkyl sulfonate, a fluoroalkyl carboxylate, a fluoroalkyl phosphate, a fluoroalkyl sulfonate or a polyoxyethylene. Derivatives, fluoroalkyl oxirane derivatives, polyethylene glycol derivatives, alkyl ammonium salts, fluoroalkyl ammonium salts, polyfluorene oxide derivatives, etc., especially derived from fluorine-containing surfactants, polyfluorene oxides Things are better. More specifically, for example, "MEGAFACF-110", "MEGAFACF-113", "MEGAFACF-120", "MEGAFACF-812, "MEGAFACF-142D", "MEGAFACF-144D", "MEGAFACF-150", " MEGAFACF-171, MEGAFACF-173, MEGAFACF-177, MEGAFACF-183, MEGAFACF-195, MEGAFACF-824, MEGAFACF-833, MEGAFACF-114, MEGAFACF- 410", "MEGAFACF-493", "MEGAFACF-494", "MEGAFACF-443", "MEGAFACF-444", "MEGAFACF-445", "MEGAFACF-446", "MEGAFACF-470", "MEGAFACF-471" , "MEGAFACF-474", "MEGAFACF-475", MEGAFACF-477, MEGAFACF-478, MEGAFACF-479, MEGAFACF-480SF, MEGAFACF-482, MEGAFACF-483, MEGAFACF-484, MEGAFACF-486, MEGAFACF -487", "MEGAFACF-489", "MEGAFACF-172D", "MEGAFACF-178K", "MEGAFACF-178RM", "MEGAFACR-08", "MEGAFACR-30", "MEGAFACF-472SF", "MEGAFACBL-20BL" -20", "MEGAFACR-61", "MEGAFACR-90", "MEGAFACESM-1", "MEGAFACMCF-350SF" (above, DIC Corporation), "Ftergent100", "Ftergent100C", "Ftergent110", " Ftergent150", "Ftergent150CH", "FtergentA", "Ftergent100A-K", "Ftergent501", "Ftergent300", "Ftergent310", "Ftergent320", "Ftergent400SW", "FTX-400P", "Ftergent251", "Ftergent215M" "Ftergent212MH", "Ftergent250", "Ftergent222F", "Ftergent212D", "FTX-218", "FTX-209F", "FTX-213F", "FTX-233F", "Ftergent245F", "FTX-208G" , "FTX-240G", FTX-206D, FTX-220D, FTX-230D, FTX-240D, FTX-207S, FTX-211S, FTX-220S, FTX-230S, FTX- 750FM, FTX-730FM, FTX-730FL, FTX-710FS, FTX-710FM, FTX-710FL, FTX-750LL, FTX-730LS, FTX-730LM , "FTX-730LL", "FTX-710LL" (above, manufactured by NEOS), BYK-300, BYK-302, BYK-306, BYK-307, BYK-310, BYK-315, BYK-320, BYK-322, BYK -323", "BYK-325", "BYK-330", "BYK-331", "BYK-333", "BYK-337", "BYK-340", "BYK-344", "BYK-370" "BYK-375", "BYK-377", "BYK-350", "BYK-352", "BYK-354", "BYK-355", "BYK-356", "BYK-358N", "BYK-361N", "BYK-357", "BYK-390", "BYK-392", "BYK-UV3500", "BYK-UV3510", "BYK-UV3570", "BYK-SiLCLeAn3700" (above, BYK Corporation, "TEGO Rad2100", "TEGO Rad2200N", "TEGO Rad2250", "TEGO Rad2300", "TEGO Rad2500", "TEGO Rad2600", "TEGO Rad2700" (above, TEGO). The amount of the surfactant to be added is preferably 0.01 to 1% by mass in the polymerizable liquid crystal composition, depending on the components other than the surfactant contained in the polymerizable liquid crystal composition, the use temperature, and the like. Further, it is contained in an amount of 0.02 to 0.5% by mass, particularly preferably 0.03 to 1% by mass. When the content is less than 0.01% by mass, it is difficult to obtain an effect of reducing variations in film thickness. The total of the content of the horizontal alignment additive having the repeating unit represented by the general formula (I) and the content of the surfactant is preferably 0.02 to 0.5% by mass, more preferably 0.05 to 0.4% by mass, particularly preferably 0.1 to 0.2. quality%.

In the polymerizable liquid crystal composition, other additives such as a thixotropic agent, a surfactant, an ultraviolet absorber, an infrared absorber, an antioxidant, a surface treatment agent, etc. may be added to the extent that the alignment ability of the liquid crystal is remarkably lowered. additive.

The optically anisotropic body of the present invention can be produced by a method in which a polymerizable liquid crystal composition having an oligomer purity control is applied to a substrate or the like, followed by curing.

The substrate used for the optical anisotropic body of the present invention is generally used for a substrate of a liquid crystal element, a display, an optical part or an optical film as long as it has a coating after being subjected to coating of the polymerizable liquid crystal composition of the present invention. In the case of a material which is heat-resistant during heating of the liquid crystal element, it is not particularly limited. Such a substrate may, for example, be an organic material such as a glass substrate, a metal substrate, a ceramic substrate or a plastic substrate. Particularly when the substrate is an organic material, for example, a cellulose derivative, a polyolefin, a polyester, a polyolefin, a polycarbonate, a polyacrylate, a polyarylate, a polyether oxime, a polyimine, a polycondensation Phenyl sulfide, polyphenylene oxide, nylon, or polystyrene. Among them, plastic substrates such as polyester, polystyrene, polyolefin, cellulose derivatives, polyarylate, and polycarbonate are preferred.

In order to improve the coatability of the polymerizable liquid crystal composition or the adhesion of the optical anisotropic body obtained by the curing, the substrate may be subjected to surface treatment. The surface treatment may, for example, be ozone treatment, plasma treatment, corona treatment, decane coupling agent treatment or the like. Further, in order to adjust the transmittance of light or the reflectance, an organic thin film, an inorganic oxide thin film, a metal thin film or the like may be provided on the surface of the substrate by vapor deposition or the like, or the substrate may be added in order to impart optical added value. It is a pickup lens, a lenticular lens, a optical disk, a retardation film, a light diffusion film, a color filter, or the like. Among them, a reading lens, a retardation film, a light diffusion film, and a color filter having a high added value are preferred.

Moreover, when the polymerizable liquid crystal composition of the present invention is applied and dried on the substrate, it is preferred to apply a normal alignment treatment or to provide an alignment film to align the polymerizable liquid crystal composition. The alignment treatment may, for example, be an extension treatment, a rubbing treatment, a polarized ultraviolet visible light irradiation treatment, an ion beam treatment, or the like. When an alignment film is used, the alignment film can be used by a well-known person. Such an alignment film may, for example, be polyamine, polyoxyalkylene, polyamine, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene oxide, polyarylate, polyethylene terephthalate. Ester, polyether oxime, epoxy resin, acrylate epoxy resin, acrylic resin, coumarin compound, chalcone, cinnamamide compound, fulgide compound, hydrazine compound, azo compound, sub A compound such as an aryl compound. The compound which is treated by the rubbing treatment is preferably added by a heating step after the alignment treatment or the alignment treatment to promote crystallization of the material. Among the compounds subjected to the alignment treatment other than the rubbing, it is preferred to use a photoalignment material.

The method for applying a polymerizable liquid crystal material to a substrate can be carried out by an applicator method, a bar coating method, a spin coating method, a gravure printing method, an offset printing method, an inkjet method, a die coating method, and a cap coating method. A well-known method such as cap coating or dip coating. It is preferred to apply a polymerizable liquid crystal composition diluted with a solvent. The solvent to be used may be any one that does not dissolve the substrate or the alignment film formed on the substrate when applied to the substrate. Further, the solvent to be used preferably has good solubility in the polymerizable cholesteric liquid crystal composition of the present invention. The solvent to be used may, for example, be an aromatic hydrocarbon such as toluene, xylene, cumene or trimethylbenzene, an ester solvent such as methyl acetate, ethyl acetate, propyl acetate or butyl acetate, methyl ethyl ketone or methyl isophthalate. a ketone solvent such as butyl ketone or cyclohexanone, tetrahydrofuran, An ether solvent such as 1,2-dimethoxyethane or methylphenyl ether, a guanamine solvent such as N,N-dimethylformamide or N-methyl-2-pyrrolidone, or propylene glycol monomethyl ether Acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, chlorobenzene, and the like. These may 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 applied by a general coating, and the solid content and the solution of the polymerizable liquid crystal composition are not particularly limited as long as the coating state is not significantly impaired. The ratio is preferably 0.1:99.9 to 80:20, and if the coating property is considered, it is preferably 1:99 to 60:40.

When a solvent is used, it is preferred to volatilize the solvent by heating at 60 to 100 ° C, more preferably 80 to 90 ° C. The heating time is preferably from 5 seconds to 3 minutes.

The polymerization operation of the polymerizable liquid crystal composition of the present invention is preferably carried out by removing the solution in the polymerizable liquid crystal composition by drying or the like, and then irradiating the general active energy ray in a state of being in a desired state. . Examples of the active energy ray include ultraviolet rays and electron beams. It is preferable to use ultraviolet rays as the active energy ray in consideration of the easiness of the device. When the polymerization is carried out by irradiation with ultraviolet light, it is preferable to irradiate ultraviolet light of 390 nm or less, and it is preferable to irradiate light of a wavelength of 250 to 370 nm. However, when the decomposition of the polymerizable liquid crystal composition is caused by ultraviolet light of 390 nm or less, polymerization treatment with ultraviolet light of 390 nm or more is preferable. The light is preferably diffused light and unpolarized light. The intensity of the ultraviolet light is preferably 1 to 100 mW/cm ^{2 , more} preferably 2 to 50 mW/cm ^{2 , and particularly} preferably 5 to 30 mW/cm ² . The irradiation energy is preferably 5 to 200 mJ/cm ^{2 , more} preferably 10 to 150 mJ/cm ^{2 , and particularly} preferably 20 to 120 mJ/cm ² .

In order to improve the solvent resistance and heat resistance of the obtained optical anisotropic body, the optical anisotropic body may be subjected to heat treatment. The heating temperature thereof is preferably such that when the organic material is used as a substrate, heating is performed in a range not exceeding the glass transition point of the substrate.

Example

Hereinafter, the present invention will be described by way of Synthesis Examples, Examples, and Comparative Examples, but the present invention is not limited thereto. Also, "%" is a quality standard unless otherwise stated. Further, the measurement of the haze value was carried out using NDH-2000 manufactured by Nippon Denshoku Industries Co., Ltd.

(Example 1)

15.18% of the polymerizable liquid crystal compound represented by the formula (A-1), 6.50% of the polymerizable liquid crystal compound represented by the formula (A-2), and 23.85% of the polymerizable liquid crystal compound represented by the formula (B-1). 32.52% of the polymerizable liquid crystal compound represented by the formula (B-2), 7.01% of the polymerizable chiral compound represented by the formula (C-1), and 8.67% of the polymerizable liquid crystal compound represented by the formula (D-1). Ep): 3.25% of the liquid crystal compound, 2.17% of the photopolymerization initiator represented by the formula (F-1), 0.44% of the photopolymerization initiator represented by the formula (F-2), p-methoxy group 0.44 parts of phenol (E-1) was used to prepare a polymerizable cholesteric liquid crystal composition (1). As a result of analyzing the oligomer contained in the polymerizable cholesteric liquid crystal composition by GPC and NMR, the total of the 3 to 4 polymer impurities (I-1) and (I-2) having a cyano group was 182 ppm. The total amount of the dimer impurities (I-3) and (I-4) having a cyano group is 1182 ppm, and the total amount of the 3~4 polymer impurities (I-5) to (I-8) having no cyano group is 43 ppm. The total amount of the 2-mer impurity (I-9) to (I-12) having no cyano group was 6385 ppm.

The Xa value calculated from (Ia) in the polymerizable cholesteric liquid crystal composition (1) was 434.

(wherein ^{one of} R ¹ and R ² is a hydrogen atom, the other represents a formula (I-1b), and m1 represents 3 or 4)

(* indicates the key node)

(wherein one of R ³ and R ⁴ is a hydrogen atom, the other represents a formula (I-2b), and m2 represents 3 or 4)

(* indicates the key node)

(wherein one of R ⁵ and R ⁶ is a hydrogen atom, and the other represents a formula (I-3b))

(* indicates the key node)

(wherein one of R ⁷ and R ⁸ is a hydrogen atom, and the other represents a formula (I-4b))

(* indicates the key node)

(wherein one of R ⁹ and R ¹⁰ is a hydrogen atom, the other represents a formula (I-5b), and m3 represents 3 or 4)

(* indicates the key node)

(wherein one of R ¹¹ and R ¹² is a hydrogen atom, the other represents a formula (I-6b), and m4 represents 3 or 4)

(* indicates the key node)

(wherein one of R ¹³ and R ¹⁴ is a hydrogen atom, the other represents a formula (I-7b), and m5 represents 3 or 4)

(* indicates the key node)

(wherein one of R ¹⁵ and R ¹⁶ is a hydrogen atom, the other represents a formula (I-8b), and m6 represents 3 or 4)

(* indicates the key node)

(wherein one of R ¹⁷ and R ¹⁸ is a hydrogen atom, and the other represents a formula (I-9b))

(* indicates the key node)

(wherein one of R ¹⁹ and R ²⁰ is a hydrogen atom, and the other represents a formula (I-10b))

(* indicates the key node)

(wherein one of R ²¹ and R ²² is a hydrogen atom, and the other represents a formula (I-11b))

(* indicates the key node)

(wherein one of R ²³ and R ²⁴ is a hydrogen atom, and the other represents a formula (I-12b))

(* indicates the key node)

In the polymerized cholesteric liquid crystal composition (1) prepared, 0.10% of polypropylene having a mass average molecular weight of 1,650 as a horizontal alignment additive was added to prepare a polymerizable cholesteric liquid crystal composition (A) of the invention. A solution of the polymerizable liquid crystal composition (1') was prepared by adding 30% of toluene and 30% of cyclohexanone to the polymerizable cholesteric liquid crystal composition (1').

Next, the polyimine solution was applied onto a glass substrate having a thickness of 0.7 mm by spin coating, dried at 100 ° C for 10 minutes, and then fired at 200 ° C for 60 minutes to obtain a coating film. The obtained coating film was subjected to a rubbing treatment to prepare a substrate for a cholesterol reflective film of the present invention. The rubbing treatment was carried out using a commercially available friction device.

Next, the solution of the polymerizable liquid crystal composition (1') was applied by spin coating to the rubbed substrate, and dried at 65 ° C for 3 minutes. The obtained coating film was placed on a hot plate at 60 ° C, and a high-pressure mercury lamp adjusted to have ultraviolet light (UV light) of only around 365 nm by a band pass filter was irradiated with UV light at an intensity of 15 mW/cm ² for 10 seconds. bell. Next, a band pass filter was taken out, and UV light was irradiated with an intensity of 70 mW/cm ² for 20 seconds, whereby an optical anisotropic body (cholesterol reflective film) of the present invention was obtained.

The film thickness of the obtained cholesterol reflective film was 55 μm. Further, the result of measuring the haze value of the film was 46%. The value of x calculated by the formula (I) is 79.

(Examples 2 to 8)

In the same manner as in Example 1, except that the polymerizable liquid crystal compound was substituted with a compound of a batch having a different purification method, the experiment was carried out. The results are shown in Table 1.

(Comparative examples 1 to 7)

In the same manner as in Example 1, except that the polymerizable liquid crystal compound was substituted with a compound of a batch having a different purification method, the experiment was carried out. The results are shown in Table 1.

From the above results, it is understood that the polymerizable liquid crystal composition of the present invention having a Xa value of 825 or less can suppress light scattering by using a haze value of 10% or less of the optical anisotropic body obtained. Further, it is understood that the optical anisotropic body obtained by the method of the present invention having an x value of 150 or less has a haze value of 10% or less and can suppress light scattering.

Claims (13)

A polymerizable liquid crystal compound having a concentration of a (ppm) impurity having a cyano group of 3 to 4, a concentration of a dimer having a cyano group of b (ppm), and a polymer having no cyano group When the concentration of the impurity is c (ppm) and the concentration of the impurity having no cyano group is d (ppm), the Xa value represented by the formula (Ia) is 825 or less, and Xa = (a + 0.19b) + 0.0215 ( c+0.19d) (Ia). The polymerizable liquid crystal composition according to claim 1, wherein the Xa value represented by the formula (Ia) is 605 or less. The polymerizable liquid crystal composition according to claim 1 or 2, wherein the polymerizable liquid crystal material contains a compound represented by the formula (a). (wherein 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, and W ³ represents a single bond, -O-, -COO- or -OCO -, v represents an integer from 0 to 18, u represents 0 or 1, and D, E and F each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-substituted 1,4-phenylene group. 1,4-cyclohexylene, 1 or 2 non-adjacent CH ₂ groups substituted with an oxygen or sulfur atom, 1,4-cyclohexylene, 1,4-cyclohexenylene, present in the formula The 1,4-phenylene group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and Y ⁶ and Y ⁷ each independently represent a single bond. -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -COO-, -OCO-, -C≡C-, -CH=CH-, -CF=CF-, -(CH ₂ ) ₄ -, -CH ₂ CH ₂ CH ₂ O-, -OCH ₂ CH ₂ CH ₂ -, -CH=CHCH ₂ CH ₂ -, -CH ₂ CH ₂ CH=CH-, -CH=CHCOO-, -OCOCH=CH -, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N- or -CH=NN=CH-, at least one of Y ⁶ and Y ⁷ , representing -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, - N=N-, -CH=NN=CH- , Y ⁸ represents a single bond, -O-, -COO-, -OCO- or -CH=CHCOO-) and/or a compound represented by the formula (b), (wherein, Z ⁵ and Z ⁶ each independently represent a hydrogen atom or a methyl group, and G, H and I each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-containing 1,4- a phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a phenylene group, a 1,4-cyclohexylene group, or a non-adjacent 2 CH ₂ group substituted with an oxygen or sulfur atom. The 1,4-phenylene group present in the group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and m represents an integer of 0 to 3, ¹ and W ² each independently represent a single bond, -O-, -COO- or -OCO-, and Y ¹ and Y ² each independently represent a single bond, -COO-, -OCO-, -CH ₂ CH ₂ COO- , -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N-, -CH=NN=CH- or single The bond, at least one of Y ¹ and Y ² , represents -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, -N=N-,- CH=NN=CH-, r and s each independently represent an integer from 2 to 18, and the 1,4-phenylene group present in the formula may also be an alkyl group having 1 to 7 carbon atoms, an alkoxy group or an alkane. Substituting one or more of a fluorenyl, cyano or halogen atom). A polymerizable liquid crystal composition according to claim 3, which contains a compound represented by a cyano group in the Z ³ system of the formula (a). The polymerizable liquid crystal composition according to claim 3 or 4, wherein the content of the compound represented by the formula (a) is from 5% to 70%. The polymerizable liquid crystal composition according to claim 3 or 4, wherein the compound represented by the formula (b) is contained in an amount of from 5% to 90%. A method for producing an optical anisotropic body by curing an active energy ray in a state in which a polymerizable liquid crystal material is aligned, and characterized in that the following polymerizable liquid crystal composition is used: when a cyano group is used The concentration of the ~4 polymer impurity is a (ppm), the concentration of the dimer impurity having a cyano group is b (ppm), the concentration of the 3~4 polymer impurity having no cyano group is c (ppm), and the cyano group is not provided. When the concentration of the dimer impurity is d (ppm) and the thickness of the optical anisotropic body obtained by curing the polymerizable liquid crystal composition is e (μm), the x value represented by the formula (I) is suppressed to 150. Hereinafter, x = [(a + 0.19b) + 0.0215 (c + 0.19d)] / e (I). The manufacturing method of claim 7, wherein the value of x represented by the formula (I) is 110 or less. The production method of the seventh or eighth aspect of the invention, wherein the polymerizable liquid crystal material contains a compound represented by the formula (a), (wherein 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, and W ³ represents a single bond, -O-, -COO- or -OCO -, v represents an integer from 0 to 18, u represents 0 or 1, and D, E and F each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-substituted 1,4-phenylene group. 1,4-cyclohexylene, 1 or 2 non-adjacent CH ₂ groups substituted with an oxygen or sulfur atom, 1,4-cyclohexylene, 1,4-cyclohexenylene, present in the formula The 1,4-phenylene group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and Y ⁶ and Y ⁷ each independently represent a single bond. -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -COO-, -OCO-, -C≡C-, -CH=CH-, -CF=CF-, -(CH ₂ ) ₄ -, -CH ₂ CH ₂ CH ₂ O-, -OCH ₂ CH ₂ CH ₂ -, -CH=CHCH ₂ CH ₂ -, -CH ₂ CH ₂ CH=CH-, -CH=CHCOO-, -OCOCH=CH -, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N- or -CH=NN=CH-, at least one of Y ⁶ and Y ⁷ , representing -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, - N=N-, -CH=NN=CH-) And/or a compound represented by the formula (b), (wherein, Z ⁵ and Z ⁶ each independently represent a hydrogen atom or a methyl group, and G, H and I each independently represent a 1,4-phenylene group, and a non-adjacent CH group is substituted with a nitrogen-containing 1,4- a phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexylene group, a phenylene group, a 1,4-cyclohexylene group, or a non-adjacent 2 CH ₂ group substituted with an oxygen or sulfur atom. The 1,4-phenylene group present in the group may be substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms, and m represents an integer of 0 to 3, ¹ and W ² each independently represent a single bond, -O-, -COO- or -OCO-, and Y ¹ and Y ² each independently represent a single bond, -COO-, -OCO-, -CH ₂ CH ₂ COO- , -CH ₂ CH ₂ OCO-, -COOCH ₂ CH ₂ -, -OCOCH ₂ CH ₂ -, -CH=N-, -N=CH-, -N=N-, -CH=NN=CH- or single The bond, at least one of Y ¹ and Y ² , represents -CH=CH-, -CH=CHCOO-, -OCOCH=CH-, -CH=N-, -N=CH-, -N=N-,- CH=NN=CH-, r and s each independently represent an integer from 2 to 18, and the 1,4-phenylene group present in the formula may also be an alkyl group having 1 to 7 carbon atoms, an alkoxy group or an alkane. Substituting one or more of a fluorenyl, cyano or halogen atom). The patentable scope of application of the manufacturing method of Item 9, comprising the general formula (a) Z ³ in the compound represented by the cyano groups. The production method according to claim 9 or 10, wherein the content of the compound represented by the formula (a) is from 5% to 70%. The manufacturing method of claim 9 or 10, wherein the compound represented by the formula (b) is contained in an amount of from 5% to 90%. An optical anisotropic body which is an optical anisotropic body using a polymerizable liquid crystal composition described below in a method of producing an optical anisotropic body by an active energy ray in a state in which a polymerizable liquid crystal material is aligned in an aligned state. : The concentration of the 3~4 polymer impurity having a cyano group is a (ppm), the concentration of the 2 polymer impurity having a cyano group is b (ppm), and the concentration of the 3~4 polymer impurity having no cyano group is c. (ppm), when the concentration of the dimer impurity having no cyano group is d (ppm), and the thickness of the optical anisotropic body obtained by curing the polymerizable liquid crystal composition is e (μm), it is represented by the formula (I) The x value is suppressed to 150 or less, and x = [(a + 0.19b) + 0.0215 (c + 0.19d)] / e (I).