Negative dispersion optical films and compounds

Abstract

Provided is a polymerizable compound containing a biphenylylene nitrile group, which is selected from the group consisting of compounds of general formula (1). Further provided are a polymerizable liquid crystal composition and an optically anisotropic body containing the polymerizable compound. The optically anisotropic body formed from the polymerizable compound is excellent in orientation unevenness and significantly improved in yellowing performance under ultraviolet light.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of light regulation, and particularly relates to a negative dispersion optical film and a compound. BACKGROUND

[0002] Polymerizable compounds (RM) are increasingly attracting attention as raw materials for various optical anisotropic bodies. The prior art generally coats an RM solution onto a substrate, aligns it, and cures it by heating or irradiating an active energy ray, thereby forming an optical anisotropic polymer film, also called an optical anisotropic body, having a uniform orientation. The orientation of the film can be planar (liquid crystal molecules are oriented substantially parallel to the layer), homeotropic (rectangular or perpendicular to the layer), or tilted, or cholesteric.

[0003] As an optical anisotropic body, at least one of the following properties is preferably all of the properties: low haze value, high film thickness uniformity, low orientation unevenness, high surface hardness, high adhesion, good appearance after ultraviolet irradiation, and low occurrence of orientation defects.

[0004] Depending on the application field, the optical anisotropic body includes, but is not limited to, a birefringent film, an optical retardation film (phase difference film), a negative dispersion optical film, an optical compensation film, a visual expansion film, a reflection film, a selective reflection film, an anti-reflection film, a brightness enhancement film, a liquid crystal alignment film, a polarizing film (polarizing plate), a polarizing element, a circularly polarizing element, an elliptically polarizing element, and other various optical elements.

[0005] In the case of a negative dispersion optical film, it is necessary to add a polymerizable compound to a parent liquid crystal to obtain a polymerizable liquid crystal composition, thereby reducing the wavelength dispersion of birefringence and effectively improving the viewing angle of a display. However, the negative dispersion optical film of the prior art is prone to yellowing and orientation unevenness.

[0006] Therefore, there is a demand for developing a polymerizable compound that can solve the above technical problems. SUMMARY

[0007] The present application aims to provide a polymerizable compound containing a biphenylnitrile group and its application to optical films. The optical anisotropic body formed by the polymerizable compound described above has excellent orientation uniformity and significantly improved yellowing performance under ultraviolet light.

[0008] The inventors have made efforts to research the polymerizable compound according to the "function-synthesis-structure" approach, and as a result, have found that the use of the polymerizable compound containing a biphenylnitrile group of the general formula (1) of the present application can solve the aforementioned technical problems, thereby completing the present application.

[0009] The present application comprises the following configurations:

[0010] A polymerizable compound containing a biphenylnitrile group, wherein the compound is selected from the group consisting of compounds of general formula (1),

[0011]

[0012] in the formula,

[0013] P1and P2each independently represent a polymerizable group;

[0014] L1and L2each independently represent an alkylene group having a carbon number of 1 to 30; the alkylene group can be linear or can have a branched group; one or more -CH2- in the alkylene group can be substituted with -O-, -S-, -NH-, -NR a -CO-, -OCO-, -COO-, -OCOO-, -SCO-, -COS-;

[0015] A1and A2each independently represent and one or more selected from the group consisting of

[0016] Z1and Z2each independently represent one or more selected from the group consisting of a single bond, -OCO-, -COO-, -OCOO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-;

[0017] x and y each independently represent an integer of 1 to 3;

[0018] R1to R2and R aeach independently represents a hydrogen atom, an alkyl group having a carbon number of 1 to 30, a halogenated alkyl group having a carbon number of 1 to 30, an alkoxy group having a carbon number of 1 to 30, a halogenated alkoxy group having a carbon number of 1 to 30, an alkenyl group having a carbon number of 2 to 30, a halogenated alkenyl group having a carbon number of 2 to 30, an alkenyloxy group having a carbon number of 2 to 30, a halogenated alkenyloxy group having a carbon number of 2 to 30, an alkylcarbonyl group having a carbon number of 1 to 30, a halogenated alkylcarbonyl group having a carbon number of 1 to 30, an alkylacyloxy group having a carbon number of 1 to 30, a halogenated alkylacyloxy group having a carbon number of 1 to 30, an alkylaryl group having a carbon number of 6 to 30, an arylalkyl group having a carbon number of 6 to 30, an alkylaryloxy group having a carbon number of 6 to 30, an arylalkyloxy group having a carbon number of 6 to 30, an arylcarbonyl group having a carbon number of 6 to 30, an aryloxycarbonyl group having a carbon number of 6 to 30, an arylcarbonyloxy group having a carbon number of 6 to 30, and an aryloxycarbonyloxy group having a carbon number of 6 to 30; one or more -CH2- in the alkyl group, the alkoxy group, the alkenyl group, the alkenyloxy group can be substituted with -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl group, the alkoxy group, the alkenyl group, the alkenyloxy group can be substituted with halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, an alkyl group having a carbon number of 1 to 30, a halogenated alkyl group having a carbon number of 1 to 30, an alkoxy group having a carbon number of 1 to 30, a halogenated alkoxy group having a carbon number of 1 to 30, an alkylacyloxy group having a carbon number of 1 to 30, a halogenated alkylacyloxy group having a carbon number of 1 to 30, or a polymerizable group;

[0019] each k independently represents an integer of 0 to 10; each of m and p independently represents an integer of 0 to 4; n represents an integer of 0 to 3; when k, m, n, and p are 2 or more, the plurality of R1and R2may be the same or different.

[0020] As the polymerizable compound described above and below, the carbon number of the alkyl group, the halogenated alkyl group, the alkoxy group, the halogenated alkoxy group, the alkylcarbonyl group, the halogenated alkylcarbonyl group, the alkylacyloxy group, or the halogenated alkylacyloxy group can be each of 1 to 28, 1 to 26, 1 to 24, 1 to 22, 1 to 20, 1 to 18, 1 to 16, 1 to 14, 1 to 12, 1 to 10, 1 to 8, 1 to 6, 1 to 4, 1 to 2, and the like, and combinations thereof; the carbon number of the alkenyl group, the halogenated alkenyl group, the alkenyloxy group, the halogenated alkenyloxy group can be each of 2 to 28, 2 to 26, 2 to 24, 2 to 22, 2 to 20, 2 to 18, 2 to 16, 2 to 14, 2 to 12, 2 to 10, 2 to 8, 2 to 6, 2 to 4, 2 to 3, and the like, and combinations thereof.

[0021] As the compound described above and below, the polymerizable group is selected from the following groups:

[0022]

[0023] in which R3 is as defined for R1 to R2.

[0024] Advantageously, each R3 independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group of carbon number 1 to 30, a haloalkyl group of carbon number 1 to 30, an alkoxy group of carbon number 1 to 30, a haloalkoxy group of carbon number 1 to 30, an alkenyl group of carbon number 2 to 30, a haloalkenyl group of carbon number 2 to 30, an alkenyloxy group of carbon number 2 to 30, a haloalkenyloxy group of carbon number 2 to 30, an alkoxycarbonyl group of carbon number 1 to 30, a haloalkoxycarbonyl group of carbon number 1 to 30, an alkylcarbonyl group of carbon number 1 to 30, a haloalkylcarbonyl group of carbon number 1 to 30, an alkylacyloxy group of carbon number 1 to 30 or a haloalkylacyloxy group of carbon number 1 to 30.

[0025] As the contextually described polymerizable compound, P1 and P2 each independently represent a group of (P-1) and (P-2); preferably, P1 and P2 each independently represent a group of (P-1).

[0026] In a particular embodiment, P1 and P2 each independently represent an acrylate group.

[0027] As the contextually described polymerizable compound, L1 and L2 each independently represent an alkylene group of carbon number 1 to 20; the alkylene group is linear; one or more -CH2- in the alkylene group can be substituted with -O-, -CO-, -OCO-, -COO-, -OCOO-.

[0028] Preferably, L1 and L2 each independently represent an alkylene group of carbon number 1 to 16. Advantageously, the alkylene group is linear. Advantageously, one or more -CH2- in the alkylene group can be substituted with -O-, -CO-.

[0029] More preferably, L1 and L2 each independently represent an alkylene group of carbon number 2 to 10.

[0030] Further preferably, L1 and L2 each independently represent an alkylene group of carbon number 3 to 8.

[0031] Most preferably, L1 and L2 each independently represent an alkylene group of carbon number 4 to 6.

[0032] As the contextually described polymerizable compound, Z1 and Z2 each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-.

[0033] Preferably, Z1and Z2each independently represent one or more of the group consisting of -OCO-, -COO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-.

[0034] More preferably, Z1and Z2each independently represent one or more of the group consisting of -OCO-, -COO-, -CH2O-, -OCH2-.

[0035] As the context of the polymerizable compound described above, wherein x and y each independently represent an integer of 1 to 2. Advantageously, x and y represent 2.

[0036] As the context of the polymerizable compound described above, wherein R1to R2and R a each independently represent alkyl of carbon number 1 to 30, haloalkyl of carbon number 1 to 30, alkoxy of carbon number 1 to 30, haloalkoxy of carbon number 1 to 30, alkenyl of carbon number 2 to 30, haloalkenyl of carbon number 2 to 30, alkenyloxy of carbon number 2 to 30, haloalkenyloxy of carbon number 2 to 30, alkylcarbonyloxy of carbon number 1 to 30, haloalkylcarbonyloxy of carbon number 1 to 30, alkylcarbonyl of carbon number 1 to 30, haloalkylcarbonyl of carbon number 1 to 30, alkylacyloxy of carbon number 1 to 30, haloalkylacyloxy of carbon number 1 to 30; one or more -CH2- in the alkyl, alkoxy, alkenyl, alkenyloxy can be substituted with -O-, -S-, -CO-, -OCO-, -COO-.

[0037] Preferably, R1to R2and R a each independently represent alkyl of carbon number 1 to 30, haloalkyl of carbon number 1 to 30, alkoxy of carbon number 1 to 30, haloalkoxy of carbon number 1 to 30. One or more -CH2- in the alkyl, alkoxy can be substituted with -O-, -S-.

[0038] More preferably, R1to R2and R a each independently represent alkyl of carbon number 2 to 20, alkoxy of carbon number 2 to 20.

[0039] Further preferably, R1to R2and R a each independently represent alkyl of carbon number 3 to 15, alkoxy of carbon number 3 to 15.

[0040] Most preferably, R1to R2and R a each independently represent alkyl of carbon number 4 to 10, alkoxy of carbon number 4 to 10.

[0041] As the context of the polymerizable compound described above, wherein R aeach independently represents a hydrogen atom, a halogen, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, a carbamoyloxy group, an amino group, an alkyl group having a carbon number of 1 to 10, a haloalkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, or a haloalkoxy group having a carbon number of 1 to 10.

[0042] Preferably, R a each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having a carbon number of 1 to 6, a haloalkyl group having a carbon number of 1 to 6, an alkoxy group having a carbon number of 1 to 6, or a haloalkoxy group having a carbon number of 1 to 6.

[0043] More preferably, R a each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having a carbon number of 1 to 4, a haloalkyl group having a carbon number of 1 to 4, an alkoxy group having a carbon number of 1 to 4, or a haloalkoxy group having a carbon number of 1 to 4.

[0044] Further preferably, R a each independently represents a hydrogen atom, a halogen, a cyano group, a methyl group, a trifluoromethyl group, a methoxy group, or a trifluoromethoxy group.

[0045] Most preferably, R a each independently represents a hydrogen atom.

[0046] as the contextually described polymerizable compound, wherein k each independently represents an integer of 0 to 5; m and p each independently represent an integer of 0 to 3; and n represents an integer of 0 to 2.

[0047] Preferably, k each independently represents an integer of 0 to 2; m and p each independently represent an integer of 0 to 2; and n represents 0 or 1.

[0048] More preferably, k, m, n, and p each represent 0.

[0049] In a preferred embodiment, as the contextually described polymerizable compound having a biphenylnitrile group, the compound is selected from the group consisting of compounds of general formula (2),

[0050]

[0051] wherein,

[0052] P1and P2, L1and L2, R1and R2, and k, m, n, and p are as defined in general formula (1).

[0053] In one specific embodiment, as the contextually described polymerizable compound having a biphenylnitrile group, the compound is selected from the group consisting of compounds P.

[0054]

[0055] In another aspect, the present application provides a polymerizable liquid crystal composition comprising the contextually described polymerizable compound.

[0056] The polymerizable liquid crystal composition described above further comprises a mother liquid crystal.

[0057] Advantageously, the mother liquid crystal described above can be commercially available.

[0058] In one specific embodiment, the polymerizable liquid crystal composition described above, wherein the mother liquid crystal comprises 50% of the compound (M-1) described in JP-A-2005-015473, 30% of the compound (M-2) described in JP-A-10-87565, and 20% of the compound (M-3) described in JP-T-2002-537280.

[0059]

[0060]

[0061] The polymerizable liquid crystal composition described above optionally further comprises an additive.

[0062] As the additive, there are included, but not limited to, polymerization initiators, sensitizers, sensitizing agents, stabilizers, leveling agents, surfactants, polymerization inhibitors, antioxidants, colorants, dispersants, lubricants, hydrophobic agents, adhesives, flow improvers, antifoaming agents, degassing agents, diluents, thixotropic agents, gelling agents, catalysts, metals, metal complexes, luminescent materials, and the like.

[0063] Advantageously, the additive is contained in an amount of 0 to 10 wt%, preferably 0.02 to 8 wt%, more preferably 0.05 to 5 wt%, and most preferably 0.1 to 2 wt%, based on the total weight of the polymerizable composition.

[0064] The polymerizable liquid crystal composition described above further comprises an organic solvent.

[0065] The organic solvent described above is preferably one which is well soluble in the polymerizable liquid crystal composition and can be removed by drying at 100°C or lower.

[0066] The organic solvent is not particularly limited, but is preferably one in which the polymerizable liquid crystal composition shows good solubility, and is preferably an aromatic solvent such as toluene, xylene, cumene, mesitylene, and the like; an ester solvent such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and the like; a ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, and the like; an ether solvent such as tetrahydrothiophene, 1,2-dimethoxyethane, anisole, and the like; an amide solvent such as N,N-dimethylformamide, N-methyl-2-pyrrolidone, and the like; propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, chlorobenzene, and the like.

[0067] The organic solvent described above can be used alone or in combination of two or more.

[0068] From the viewpoint of solution stability, it is preferable to use one or more of a ketone-based solvent, an ether-based solvent, an ester-based solvent, and an aromatic solvent.

[0069] As the polymerizable liquid crystal composition described above, the content of the organic solvent is preferably 25 to 95% by weight, more preferably 30 to 90% by weight, even more preferably 35 to 85% by weight, and most preferably 40 to 80% by weight, based on the total weight of the polymerizable liquid crystal composition.

[0070] In the preparation of the solution of the polymerizable liquid crystal composition, heating and / or stirring are advantageously performed in order to promote the dissolution of the polymerizable liquid crystal composition.

[0071] Further, a cured product is formed by coating the polymerizable liquid crystal composition described above on a substrate and curing it.

[0072] The coating method includes, but is not limited to, a coater method, a bar coating method, a spin coating method, a gravure printing method, a flexographic printing method, an inkjet method, a die coating method, a CAP coating method, and a dipping method, and the like known in the art. After the polymerizable liquid crystal composition is coated, it is cured (dried).

[0073] Advantageously, the curing is performed by polymerization. In the polymerization of the polymerizable liquid crystal composition, it is desirable to perform the polymerization rapidly, and thus it is preferable to polymerize it by irradiation of active energy rays such as ultraviolet visible light or electron rays. In the case of using ultraviolet visible light, a polarized light source can be used, or a non-polarized light source can be used.

[0074] The substrate of the cured product includes, but is not limited to, a glass substrate, a metal substrate, a ceramic substrate, and a polymer substrate. Further, as the polymer substrate, for example, a cellulose derivative, a polyolefin, a polyester, a polyolefin, a polycarbonate, a polyacrylate, a polyarylate, a polyethersulfone, a polyamide, a polyimide, a polyphenylene sulfide, a polyphenylene ether, or a polystyrene, and the like can be used.

[0075] From the viewpoint of process suitability, in particular, from the viewpoint of heat resistance and chemical stability, it is preferable to use a polyester, a polystyrene, a polyolefin, a cellulose derivative, a polyarylate, and a polycarbonate.

[0076] In another aspect, the present application also provides an optically anisotropic body including a substrate, a polymer film formed of the cured product of the polymerizable liquid crystal composition described above, and an alignment film, if necessary.

[0077] Advantageously, the substrate, the alignment film, if necessary, and the polymer film formed of the cured product of the polymerizable liquid crystal composition are sequentially laminated to form the optically anisotropic body.

[0078] The alignment film material includes, but is not limited to, polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, acrylic resin, epoxy-acrylic resin, coumarin, chalcone, cinnamate, anthraquinone, azo compound, aryl ethylene compound, and the like. Based on process applicability, especially based on heat resistance and chemical stability considerations, polyimide is preferred.

[0079] Advantageously, the alignment film is subjected to an alignment treatment. The alignment treatment can be a stretching treatment, a rubbing treatment, polarized ultraviolet-visible light irradiation, ion beam treatment, or the like. The alignment treatment is preferably a rubbing treatment or polarized ultraviolet-visible light irradiation.

[0080] In another aspect, the present application provides an optically anisotropic body formed from the cured product described above and / or use of the optically anisotropic body in optical, optoelectronic, electronic, semiconductor components or devices.

[0081] The use described above includes, but is not limited to, birefringent film, optical retardation film (phase difference film), negative dispersion optical film, optical compensation film, visual expansion film, reflective film, selective reflection film, anti-reflection film, brightness enhancement film, liquid crystal alignment film, polarizing film (polarizing plate), polarizing element, circularly polarizing element, elliptically polarizing element.

[0082] Preferably, the use is a negative dispersion optical film.

[0083] The negative dispersion optical film described above is superior in alignment uniformity and also significantly improves yellowing performance under ultraviolet light. Therefore, each of the compounds described above can be used as a component of a polymerizable composition. Furthermore, the optically anisotropic body using the polymerizable liquid crystal composition containing the compound of the present application can be used for optical films and the like. DETAILED DESCRIPTION

[0084] In the present application, technical terms are further explained and defined in detail.

[0085] The term "liquid crystal" or "mesogenic compound" means a compound that forms a mesophase or a liquid crystal phase under certain conditions.

[0086] The term "polymerizable mesogen" or "polymerizable compound" abbreviated as RM means a polymerizable liquid crystal or mesogenic compound, and particularly means a monomeric compound.

[0087] The term "mono-reactivity" or "di-reactivity" means that the polymerizable mesogen or polymerizable compound has one or two polymerizable groups.

[0088] The term "polymerizable group" means a group that forms a polymer of higher molecular weight by polymerization through light, heat, or catalyst, etc.

[0089] The term "film" means a rigid or flexible coating or layer having mechanical stability; optionally, the film can exist alone; on a support substrate; or sandwiched between two substrates.

[0090] The present application is further illustrated by the following synthesis examples and examples, which do not limit the application. Unless otherwise stated, the percentages in the examples are all mass percentages.

[0091] Synthesis Example

[0092] The compound P of the present application is synthesized.

[0093]

[0094] The synthesis route of the compound P is as follows:

[0095]

[0096] Preparation of intermediate S-3

[0097] 40 g of compound S-1 and 53.2 g of compound S-2 are added to a 500 ml reaction flask, and 400 g of dichloromethane and 5.4 g of DMAP are added. Then, the temperature is lowered to 0°C, and a dichloromethane solution of DCC (50 g dissolved in 120 g of dichloromethane) is added dropwise. After the dropwise addition is completed, the temperature is raised to 25°C, and the reaction is carried out for 12 h. After the treatment, the filter cake is washed with dichloromethane, and the liquid phase is left. The liquid phase is washed with 200 g of 5% hydrochloric acid, and then washed twice with 200 g of water. The organic phase is dried, and recrystallized with 800 g of methanol and 80 g of dichloromethane after the eluent is added with 0.07 g of p-methoxyphenol and then dissolved under reduced pressure. 70 g of intermediate S-3 is obtained with a yield of 80%.

[0098] Preparation of intermediate S-4

[0099] 70 g of intermediate S-3 is added to a 1000 ml three-necked flask, and 200 ml of dichloromethane, 13.9 g of hydrogen peroxide, 0.5 g of 4-OH-TEMPO, 2.4 g of sodium dihydrogen phosphate, and 200 g of water are added. The temperature is raised to 35°C, and an aqueous solution of sodium chlorite (12.9 g dissolved in 150 g of water) is added dropwise. After the dropwise addition is completed, the reaction is carried out for 2 h. The reaction liquid is filtered, and a solid is obtained. The solid is slurried with 200 g of isopropyl alcohol, and then filtered and dried to obtain 64.6 g of intermediate S-4 with a yield of 94%.

[0100] Preparation of product P

[0101] Into a 500-ml reaction flask, 60 g of intermediate S-4 and 14 g of compound S-5 were charged, 300 g of dichloromethane and 2 g of DMAP were added, and then the mixture was cooled to 0°C, and a dichloromethane solution (16 g dissolved in 60 g of dichloromethane) of DCC was added dropwise thereto. After the dropwise addition was completed, the mixture was warmed to 25°C, and reacted for 12 h. After the reaction, the mixture was filtered, the filter cake was washed with dichloromethane, and the filtrate was subjected to a post-treatment. The filtrate was washed with 100 g of 5% hydrochloric acid and then washed twice with 100 g of water. The organic phase was dried, and then recrystallized from 600 g of methanol and 60 g of dichloromethane. Thus, 59 g of product P was obtained in a yield of 82%.

[0102] NMR data are as follows, 1 H NMR (CDCI3) δ: 1.45-1.47 (t, 8H), 1.51-1.53 (t, 8H), 1.61-1.63 (t, 2H), 1.78-1.79 (t, 8H), 1.82-1.84 (t, 8H), 2.44-2.46 (t, 2H), 3.94-3.96 (t, 4H), 3.98-4.01 (t, 4H), 4.14-4.16 (d, 4H), 5.20-5.22 (d, 4H), 6.15-6.17 (d, 2H), 6.83 (s, 1H), 6.84-6.87 (d, 9H), 6.91-6.92 (d, 2H), 6.94 (d, 1H), 7.55-7.56 (d, 2H), 7.65-7.66 (d, 2H), 7.62-7.63 (d, 2H).

[0103] Example 1 and Comparative Examples 1 to 3

[0104] Example 1 uses the compound P of the present application.

[0105] Comparative Examples 1 to 3 use known compounds B-1 to B-3 of the prior art.

[0106]

[0107] In order to evaluate the uneven orientation property and the yellowing property of a negative dispersion optical film, a liquid crystal composition was provided as a parent liquid crystal (M). The liquid crystal composition contained 50% of a compound (M-1) described in JP-A-2005-015473, 30% of a compound (M-2) described in JP-A-10-87565, and 20% of a compound (M-3) described in JP-T-2002-537280.

[0108]

[0109] The alignment film was coated with a polyimide solution on a glass substrate having a thickness of 0.7 mm, dried at 100°C, and after 10 minutes, baked at 200°C for 60 minutes, thereby obtaining an alignment film. The obtained alignment film was subjected to rubbing treatment using a commercially available rubbing device.

[0110] A polymerizable liquid crystal composition was prepared by adding 40% of the compound as an evaluation object to a mother liquid crystal M, and further adding 1% of a photopolymerization initiator Irgacure 907 (BASF Corporation), 0.1% of 4-methoxyphenol, and 80% of chloroform. A coating liquid was prepared by further adding 0.1% of 4-methoxyphenol to the polymerizable liquid crystal composition.

[0111] The coating liquid was coated on the rubbed alignment film by a spin coating method. After drying at 80°C for 1 minute, further drying at 120°C for 1 minute, and then irradiation of ultraviolet rays at an intensity of 40 mW / cm 2 for 25 seconds using a high-pressure mercury lamp, an evaluation object negative dispersion optical film was produced.

[0112] The obtained negative dispersion optical film was evaluated for the degree of unevenness by polarizing microscope observation. Ten pieces of negative dispersion optical film each added with the compound as an evaluation object were produced, and the number of unevenness was counted. The number of unevenness observed in the 10 pieces of negative dispersion optical film was totaled, and if the number of unevenness was 0, it was rated as excellent, if the number of unevenness was 1, it was rated as good, if the number of unevenness was 1-10, it was rated as fair, and if the number of unevenness was more than ten, it was rated as poor.

[0113] Each of the produced negative dispersion optical films was subjected to a solarization test using a xenon irradiation tester (Suntest XLS, ATLAS Corporation) under conditions of 60 mW / cm 2 , 26°C, and 120 J. The obtained negative dispersion optical film was evaluated for yellowing properties and orientation unevenness properties.

[0114] The yellowing properties were evaluated using a yellowness index (YI). The difference (△YI) between the YI value before the solarization test and the YI value after the solarization test was calculated. The yellowness index (YI) was measured using a JASCO UV / VIS spectrophotometer V-560 and calculated by a color diagnosis program attached thereto. The calculation formula is represented as: YI = 100 (1.28X - 1.06Z) / Y (JIS K7373) (X, Y, Z represent three stimulus values in XYZ color system, and the smaller the value of △YI, the less the discoloration.

[0115] Table 1

[0116] Membrane The compound to be evaluated used Example 1 Compound P of the invention Comparative example 1 Comparative compound B-1 Comparative example 2 Comparative compound B-2 Comparative example 3 Comparative compound B-3

[0117] Table 2

[0118]

[0119]

[0120] As seen from Table 2, the negative dispersion optical film of Example 1 is excellent in orientation unevenness and significantly improved in yellowing performance under ultraviolet light. Therefore, the compound of the present application is useful as a component of a polymerizable composition. Furthermore, an optically anisotropic body using a polymerizable liquid crystal composition containing the compound of the present application is useful as a negative dispersion optical film or the like.

[0121] It should be understood that the detailed description and specific examples, which were given above, are merely by way of illustration of the spirit and principles of the present application, and are not intended to limit the scope of the present application. Furthermore, it should be understood that various modifications, substitutions, eliminations, corrections or adjustments of the technical solutions of the present application can be made by those skilled in the art after reading the content of the present application, and these equivalent technical solutions also fall within the scope defined by the claims of the present application.

Claims

1. A polymerizable compound containing a biphenyl nitrile group, characterized in that, The compound is selected from compounds of general formula (2). In the formula, P1 and P2 each independently represent the following polymerizable groups; L1 and L2 each independently represent straight-chain alkylene groups with 1-30 carbon atoms; R1 and R2 represent hydrogen atoms; k independently represents integers from 0 to 10; m and p independently represent integers from 0 to 4; n represents integers from 0 to 3; R3 represents an alkyl group with 1-30 carbon atoms and hydrogen atoms.

2. A polymerizable liquid crystal composition, characterized in that, It contains the polymerizable compound according to claim 1.

3. An optically anisotropic body, characterized in that, It is formed from the polymeric liquid crystal composition according to claim 2.

4. The optical anisotropic body according to claim 3, wherein, The optical anisotropy body is selected from negative dispersion optical films.

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