Negative dispersion optical film and compound

Abstract

Provided are biphenylcarbonitrile-containing polymerizable compounds, the compounds being compounds of general formula (1). Further provided are a polymerizable liquid crystal composition containing the polymerizable compounds and an optically anisotropic body. The optically anisotropic body formed from the polymerizable compound has excellent optical anisotropy unevenness, and the yellowing performance under ultraviolet light is remarkably relieved.

Description

Negative dispersion optical films and compounds Technical Field

[0001] The present invention belongs to the technical field of light regulation, and in particular relates to a negative dispersion optical film and a compound. Background Art

[0002] Polymerizable compounds (RMs) are gaining increasing attention as raw materials for preparing various optically anisotropic materials. Existing techniques typically involve coating a RM solution onto a substrate, aligning it, and curing it by heating or irradiating it with active energy rays. This results in a uniformly oriented optically anisotropic polymer film, also known as an optically anisotropic material. The film's orientation can be planar (liquid crystal molecules oriented substantially parallel to the layers), homeotropic (rectangular or perpendicular to the layers), or tilted, or even cholesteric.

[0003] The optically anisotropic body has at least one of the following characteristics, preferably all of them: low haze value, high film thickness uniformity, little orientation unevenness, high surface hardness, high adhesion, good appearance after ultraviolet irradiation, and little orientation defect.

[0004] Depending on the application field, optical anisotropic bodies include, but are not limited to, birefringent films, optical delay films (phase difference films), negative dispersion optical films, optical compensation films, vision expansion films, reflective films, selective reflective films, anti-reflective films, brightness enhancement films, liquid crystal orientation films, polarizing films (deflecting plates), polarizing elements, circular polarizing elements, elliptically polarizing elements, and various other optical elements.

[0005] In the case of negative dispersion optical films, a polymerizable compound is added to the parent liquid crystal to produce a polymerizable liquid crystal composition. This reduces the wavelength dispersion of the birefringence, effectively increasing the viewing angle of the display. However, existing negative dispersion optical films are prone to yellowing and uneven orientation.

[0006] Therefore, there is a demand for the development of the following polymerizable compound, the use of which can solve the above-mentioned technical problems.

[0007] Summary of the Invention

[0008] The present invention aims to provide a polymerizable compound containing a biphenylnitrile group and its application in an optical film. The polymerizable compound described above has excellent optical anisotropy and poor orientation, and also significantly improves yellowing performance under ultraviolet light.

[0009] The inventors have diligently studied the molecular engineering of polymerizable compounds according to the "function-synthesis-structure" approach and found that the aforementioned technical problems can be solved by using the polymerizable compounds containing biphenylnitrile groups of the general formula (1) of the present invention, thereby completing the present invention.

[0010] The present invention comprises the following structures:

[0011] A polymerizable compound containing a biphenylnitrile group, wherein the compound is selected from the compounds of general formula (1),

[0012] Where,

[0013] P1 and P2 each independently represent a polymerizable group;

[0014] L1 and L2 each independently represent an alkylene group with 1 to 30 carbon atoms; the alkylene group may be linear or branched; one or more -CH2- in the alkylene group may be replaced by -O-, -S-, -NH-, -NR a -, -CO-, -OCO-, -COO-, -OCOO-, -SCO-, -COS-substituted;

[0015] A1 and A2 each independently represent One or more of the groups consisting of;

[0016] Z1 and Z2 each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -OCOO-, -CH2O-, -OCH2-, -CF2O-, and -OCF2-;

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

[0018] R1-R2 and R aEach independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, Alkylcarbonyl, halogenated alkylcarbonyl having 1 to 30 carbon atoms, alkylacyloxy having 1 to 30 carbon atoms, halogenated alkylacyloxy having 1 to 30 carbon atoms, alkylaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, alkylaryloxy having 6 to 30 carbon atoms, arylalkyloxy having 6 to 30 carbon atoms, arylcarbonyl having 6 to 30 carbon atoms, aryloxycarbonyl having 6 to 30 carbon atoms, arylcarbonyloxy having 6 to 30 carbon atoms, and 6-30 aryloxycarbonyloxy; one or more -CH2- in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl and alkenyloxy groups may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyanato, alkyl having 1-30 carbon atoms, haloalkyl having 1-30 carbon atoms, alkoxy having 1-30 carbon atoms, haloalkoxy having 1-30 carbon atoms, alkylacyloxy having 1-30 carbon atoms, haloalkylacyloxy having 1-30 carbon atoms or a polymerizable group;

[0019] k each independently represents an integer of 0-10; m and p each independently represent an integer of 0-4; n represents an integer of 0-3; when k, m, n and p ≥ 2, multiple R1s and R2s may be the same or different.

[0020] As the polymerizable compounds described above and below, the carbon number of the alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, alkoxycarbonyl group, haloalkoxycarbonyl group, alkylcarbonyl group, haloalkylcarbonyl group, alkylacyloxy group or haloalkylacyloxy group, which is 1-30, may be 1-28, 1-26, 1-24, 1-22, 1-20, 1-18, 1-16, 1-14, 1-12, 1-10, 1-8, 1-6, 1-4, 1-2, and various subranges thereof, and combinations thereof; the carbon number of the alkenyl group, haloalkenyl group, alkenyloxy group or haloalkenyloxy group may be 2-28, 2-26, 2-24, 2-22, 2-20, 2-18, 2-16, 2-14, 2-12, 2-10, 2-8, 2-6, 2-4, 2-3, and various subranges thereof, and combinations thereof.

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

[0022] Wherein, R3 has the same definition as R1-R2.

[0023] Advantageously, R3 each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkylacyloxy group having 1 to 30 carbon atoms, or a haloalkylacyloxy group having 1 to 30 carbon atoms.

[0024] As the polymerizable compound described above and below, wherein 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).

[0025] In a specific embodiment, P1 and P2 each independently represent an acrylate group.

[0026] As the polymerizable compound described above and below, wherein L1 and L2 each independently represent an alkylene group having 1 to 20 carbon atoms; the alkylene group is linear; and one or more -CH2- in the alkylene group may be substituted by -O-, -CO-, -OCO-, -COO-, or -OCOO-.

[0027] Preferably, L1 and L2 each independently represent an alkylene group having 1 to 16 carbon atoms. Advantageously, the alkylene group is linear. Advantageously, one or more -CH2- groups in the alkylene group may be substituted by -O- or -CO-.

[0028] More preferably, L1 and L2 each independently represent an alkylene group having 2 to 10 carbon atoms.

[0029] More preferably, L1 and L2 each independently represent an alkylene group having 3 to 8 carbon atoms.

[0030] Most preferably, L1 and L2 each independently represent an alkylene group having 4 to 6 carbon atoms.

[0031] As the polymerizable compound described above and below, wherein Z1 and Z2 each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -CH2O-, -OCH2-, -CF2O-, and -OCF2-.

[0032] Preferably, Z1 and Z2 each independently represent one or more of the group consisting of -OCO-, -COO-, -CH2O-, -OCH2-, -CF2O-, and -OCF2-.

[0033] More preferably, Z1 and Z2 each independently represent one or more of the group consisting of -OCO-, -COO-, -CH2O-, and -OCH2-.

[0034] As the polymerizable compound described above and below, wherein x and y each independently represent an integer of 1 to 2. Advantageously, x and y represent 2.

[0035] As the polymerizable compound described above and below, wherein R1-R2 and R a Each independently represents an alkyl group having 1-30 carbon atoms, a haloalkyl group having 1-30 carbon atoms, an alkoxy group having 1-30 carbon atoms, a haloalkoxy group having 1-30 carbon atoms, an alkenyl group having 2-30 carbon atoms, a haloalkenyl group having 2-30 carbon atoms, an alkenyloxy group having 2-30 carbon atoms, a haloalkenyloxy group having 2-30 carbon atoms, an alkoxycarbonyl group having 1-30 carbon atoms, a haloalkoxycarbonyl group having 1-30 carbon atoms, an alkylcarbonyl group having 1-30 carbon atoms, a haloalkylcarbonyl group having 1-30 carbon atoms, an alkylacyloxy group having 1-30 carbon atoms, or a haloalkylacyloxy group having 1-30 carbon atoms; and one or more -CH2- groups in the alkyl group, alkoxy group, alkenyl group, or alkenyloxy group may be substituted by -O-, -S-, -CO-, -OCO-, or -COO-.

[0036] Preferably, R1-R2 and R a Each independently represents an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or a haloalkoxy group having 1 to 30 carbon atoms. One or more -CH2- groups in the alkyl group or alkoxy group may be substituted with -O- or -S-.

[0037] More preferably, R1-R2 and R a Each independently represents an alkyl group having 2 to 20 carbon atoms or an alkoxy group having 2 to 20 carbon atoms.

[0038] More preferably, R1-R2 and R a Each independently represents an alkyl group having 3 to 15 carbon atoms or an alkoxy group having 3 to 15 carbon atoms.

[0039] Most preferably, R1-R2 and R a Each independently represents an alkyl group having 4 to 10 carbon atoms or an alkoxy group having 4 to 10 carbon atoms.

[0040] As the polymerizable compound described above and below, 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 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a haloalkoxy group having 1 to 10 carbon atoms.

[0041] Preferably, R a Each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a haloalkoxy group having 1 to 6 carbon atoms.

[0042] More preferably, R a Each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms.

[0043] More 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.

[0044] Most preferably, R a Each independently represents a hydrogen atom.

[0045] As the polymerizable compound described above and below, wherein k each independently represents an integer of 0-5; m and p each independently represent an integer of 0-3; and n represents an integer of 0-2.

[0046] Preferably, k each independently represents an integer of 0-2; m and p each independently represent an integer of 0-2; and n represents 0 or 1.

[0047] More preferably, k, m, n and p all represent 0.

[0048] In a preferred embodiment, as the polymerizable compound containing a biphenylnitrile group as described above and below, wherein the compound is selected from the compounds of general formula (2),

[0049] in,

[0050] P1 and P2, L1 and L2, R1 and R2, as well as k, m, n and p are as defined in the general formula (1).

[0051] In a specific embodiment, the polymerizable compound containing a biphenylnitrile group as described above and below is selected from compound P.

[0052] In yet another aspect, the present invention provides a polymerizable liquid crystal composition comprising the polymerizable compound described above and below.

[0053] The polymerizable liquid crystal composition described above and below further includes a matrix liquid crystal.

[0054] Advantageously, the parent liquid crystals as described above and below are commercially available.

[0055] In a specific embodiment, as the polymerizable liquid crystal composition described in the context, the mother liquid crystal contains 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.

[0056] The polymerizable liquid crystal composition described above and below optionally further contains additives.

[0057] Additives include, but are not limited to, polymerization initiators, sensitizers, sensitizers, stabilizers, leveling agents, surfactants, inhibitors, antioxidants, colorants, dispersants, lubricants, hydrophobic agents, adhesives, flow improvers, defoamers, degassing agents, diluents, thixotropic agents, gelling agents, catalysts, metals, metal complexes, luminescent materials, and the like.

[0058] Advantageously, the additive is present in an amount of 0-10 wt%, preferably 0.02-8 wt%, more preferably 0.05-5 wt%, and most preferably 0.1-2 wt%, based on the total weight of the polymerizable composition.

[0059] The polymerizable liquid crystal composition described above and below further includes an organic solvent.

[0060] As the organic solvent mentioned above and below, it is preferred that the organic solvent has good solubility in the polymerizable liquid crystal composition and can be removed by drying at 100° C. or below.

[0061] The organic solvent is not particularly limited, but an organic solvent in which the polymerizable liquid crystal composition shows good solubility is preferred, preferably an aromatic solvent such as toluene, xylene, isopropyl benzene, mesitylene, etc.; an ester solvent such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc.; a ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.; an ether solvent such as tetrahydrothiophene, 1,2-dimethoxyethane, anisole, etc.; an amide solvent such as N,N-dimethylformamide, N-methyl-2-pyrrolidone, etc.; propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, and chlorobenzene, etc.

[0062] The organic solvents described above and below may be used alone or in combination of two or more.

[0063] Considering the stability of the solution, it is preferred to use one or more of ketone solvents, ether solvents, ester solvents and aromatic solvents.

[0064] As the polymerizable liquid crystal composition described above and below, the organic solvent content is 25-95wt%, preferably 30-90wt%, more preferably 35-85wt%, and most preferably 40-80wt%, based on the total weight of the polymerizable liquid crystal composition.

[0065] When preparing a polymerizable liquid crystal composition solution, heating and / or stirring are advantageously performed to promote dissolution of the polymerizable liquid crystal composition.

[0066] Furthermore, the polymerizable liquid crystal composition described above and below is coated on a substrate and cured to form a cured product.

[0067] Coating methods include, but are not limited to, coater coating, rod coating, spin coating, gravure printing, flexographic printing, inkjet coating, die coating, CAP coating, dipping, and other methods known in the art. After coating the polymerizable liquid crystal composition, it is cured (dried).

[0068] Advantageously, curing is carried out by polymerization. When polymerizing the polymerizable liquid crystal composition, it is desired to polymerize rapidly, so it is preferably polymerized by irradiating it with active energy rays such as ultraviolet-visible light or electron beams. When ultraviolet-visible light is used, a polarized light source or a non-polarized light source can be used.

[0069] 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. Furthermore, the polymer substrate may be, for example, a cellulose derivative, polyolefin, polyester, polyolefin, polycarbonate, polyacrylate, polyarylate, polyethersulfone, polyamide, polyimide, polyphenylene sulfide, polyphenylene oxide, or polystyrene, among others.

[0070] Based on process suitability, especially heat resistance and chemical stability, polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, and polycarbonate are preferred.

[0071] In another aspect, the present invention further provides an optically anisotropic body comprising a substrate, a polymer film formed from the cured polymerizable liquid crystal composition as described above and below, and, if necessary, an alignment film.

[0072] Advantageously, the optically anisotropic body is formed by laminating a substrate, an alignment film if necessary, and a polymer film formed of a cured product of a polymerizable liquid crystal composition in this order.

[0073] Materials for the alignment film include, but are not limited to, polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene oxide, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, acrylic resin, epoxy acrylic resin, coumarin, chalcone, cinnamate, anthraquinone, azo compounds, and aromatic vinyl compounds. Polyimide is preferred based on process applicability, especially heat resistance and chemical stability.

[0074] Advantageously, the oriented film is obtained by an orientation treatment, which may be a stretching treatment, a rubbing treatment, polarized ultraviolet-visible light irradiation, an ion beam treatment, etc. Preferably, the orientation treatment is a rubbing treatment or polarized ultraviolet-visible light irradiation.

[0075] In yet another aspect, the present invention provides an optically anisotropic body formed from the cured product described above and below and / or use of the optically anisotropic body in optical, optoelectronic, electronic, or semiconductor components or devices.

[0076] The applications described in the context include, but are not limited to, birefringent films, optical delay films (phase difference films), negative dispersion optical films, optical compensation films, vision enlargement films, reflective films, selective reflective films, anti-reflective films, brightness enhancement films, liquid crystal orientation films, polarizing films (deflecting plates), polarizing elements, circular polarizing elements, and elliptically polarizing elements.

[0077] Preferably, the application is a negative dispersion optical film.

[0078] The negative dispersion optical films described above and below exhibit excellent orientational malalignment and significantly improve yellowing performance under ultraviolet light. Therefore, each of the compounds described above and below can be used as a component of a polymerizable composition. Furthermore, optically anisotropic polymerizable liquid crystal compositions containing the compounds of the present invention can be used in optical films and other applications. DETAILED DESCRIPTION

[0079] In the present invention, technical terms are further explained and defined in detail.

[0080] The term "liquid crystal" or "mesogenic compound" refers to a compound that forms a mesomorphic phase or a liquid crystal phase under certain conditions.

[0081] The term "polymerizable mesogen" or "polymerizable compound", abbreviated as RM, refers to a polymerizable liquid crystal or mesogenic compound, in particular a monomeric compound.

[0082] The term "monoreactive" or "direactive" means that the polymerizable mesogen or polymerizable compound has one or two polymerizable groups.

[0083] The term "polymerizable group" refers to a group that is polymerized by light, heat, a catalyst, or the like to form a polymer having a higher molecular weight.

[0084] The term "film" refers to a mechanically stable rigid or flexible coating or layer; optionally, the film can be alone; on a supporting substrate; or sandwiched between two substrates.

[0085] The present invention is further described below in conjunction with synthesis examples and embodiments, but the application of the present invention is not limited thereto. Unless otherwise specified, the percentages in the embodiments are all by mass.

[0086] Synthesis example

[0087] Synthesis of compound P of the present invention.

[0088] The synthetic route of compound P is as follows:

[0089] Preparation of intermediate S-3

[0090] 40g of compound S-1 and 53.2g of compound S-2 were added to a 500ml reaction flask, followed by 400g of dichloromethane and 5.4g of DMAP. The temperature was then lowered to 0°C, and a dichloromethane solution of DCC (50g dissolved in 120g of dichloromethane) was added dropwise. After the addition was complete, the temperature was raised to 25°C and the reaction was allowed to proceed for 12h. For post-processing, the filter cake was washed with dichloromethane, and the liquid phase was washed with 200g of 5% hydrochloric acid and then twice with 200g of water. After drying, the organic phase was passed through a silica gel column. 0.07g of p-methoxyphenol was added to the eluate, and the solvent was removed under reduced pressure. The product was recrystallized from 800g of methanol and 80g of dichloromethane. 70g of intermediate S-3 was obtained, with a yield of 80%.

[0091] Preparation of intermediate S-4

[0092] 70g of intermediate S-3 was added to a 1000ml three-necked flask, followed by 200ml of dichloromethane, 13.9g of hydrogen peroxide, 0.5g of 4-OH-TEMPO, 2.4g of sodium dihydrogen phosphate, and 200g of water. The mixture was warmed to 35°C and an aqueous sodium chlorite solution (12.9g dissolved in 150g of water) was added dropwise. The mixture was incubated for 2h. The reaction solution was filtered to obtain a solid. 200g of isopropyl alcohol was used for pulping, followed by suction filtration and drying to obtain 64.6g of intermediate S-4, with a yield of 94%.

[0093] Preparation of Product P

[0094] 60g of intermediate S-4 and 14g of compound S-5 were added to a 500ml reaction flask, followed by 300g of dichloromethane and 2g of DMAP. The temperature was then lowered to 0°C, and a dichloromethane solution of DCC (16g dissolved in 60g of dichloromethane) was added dropwise. After the addition was complete, the temperature was raised to 25°C and the reaction was allowed to proceed for 12h. For post-processing, the mixture was first filtered and the filter cake washed with dichloromethane. The remaining liquid phase was washed with 100g of 5% hydrochloric acid and then twice with 100g of water. The organic phase was dried and passed through a silica gel column. 0.1g of p-methoxyphenol was added to the eluate, followed by desolvation under reduced pressure and recrystallization from 600g of methanol and 60g of dichloromethane. 59g of product P was obtained, with a yield of 82%.

[0095] The NMR data are as follows, 1 H NMR(CDCl3)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).

[0096] Example 1 and Comparative Examples 1-3

[0097] Example 1 uses compound P of the present invention.

[0098] Comparative Examples 1-3 used compounds B-1 to B-3 known in the prior art.

[0099] To evaluate the orientation unevenness and yellowing properties of a negative dispersion optical film, a liquid crystal composition was provided as a mother liquid crystal (M). The liquid crystal composition contained 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.

[0100] A polyimide solution for an alignment film was applied to a glass substrate having a thickness of 0.7 mm, dried at 100° C. for 10 minutes, and then fired at 200° C. for 60 minutes to obtain an alignment film. The obtained alignment film was subjected to a rubbing treatment using a commercially available rubbing device.

[0101] 40% of the compound to be evaluated was added to the mother liquid crystal M to prepare a polymerizable liquid crystal composition; 1% of a photopolymerization initiator Irgacure 907 (BASF), 0.1% 4-methoxyphenol and 80% chloroform were further added to prepare a coating solution.

[0102] The coating solution was applied to the rubbed alignment film by spin coating. After drying at 80°C for 1 minute, it was further dried at 120°C for 1 minute, and then heated at 40 mW / cm2 using a high-pressure mercury lamp. 2 The negative dispersion optical film to be evaluated was produced by irradiating the film with ultraviolet light at an intensity of 100 nm for 25 seconds.

[0103] The resulting negative dispersion optical film was observed under a polarizing microscope to evaluate the degree of unevenness. Ten negative dispersion optical films were prepared, each containing the compound to be evaluated, and the number of uneven spots was counted. The number of uneven spots observed in all ten negative dispersion optical films was totaled. A score of 0 was rated excellent, 1 was rated good, 1-10 was rated fair, and 10 or more was rated poor.

[0104] A xenon irradiation tester (Suntest XLS, ATLAS) was used at 60 mW / cm 2 Each of the negative dispersion optical films produced was subjected to a sunlight test under the conditions of 26° C., 120 J. The yellowing performance and orientation unevenness performance of the negative dispersion optical films obtained were evaluated.

[0105] Yellowing performance was evaluated using the Yellowness Index (YI). The difference (ΔYI) between the YI value before and after the sun exposure test was calculated. The Yellowness Index (YI) was measured using a JASCO UV / VIS Spectrophotometer V-560 and calculated using the included color diagnosis program. The calculation formula is: YI = 100 (1.28X - 1.06Z) / Y (JIS K7373) (X, Y, and Z represent the tristimulus values ​​in the XYZ color system. A smaller ΔYI value indicates less discoloration).

[0106] Table 1

[0107] Table 2

[0108] As can be seen from Table 2, the negative dispersion optical film of Example 1 exhibits excellent orientation malalignment and significantly improved yellowing performance under UV light. Therefore, the compounds of the present invention can be used as components of polymerizable compositions. Furthermore, optically anisotropic polymerizable liquid crystal compositions containing the compounds of the present invention can be used in negative dispersion optical films, etc.

[0109] It should be understood that the specific embodiments of the present invention are intended only to illustrate the spirit and principles of the present invention and are not intended to limit the scope of the present invention. Furthermore, it should be understood that after reading the contents of the present invention, those skilled in the art may make various changes, substitutions, deletions, corrections, or adjustments to the technical solutions of the present invention, and that such equivalent technical solutions also fall within the scope defined by the claims of the present invention.

Claims

1. A polymerizable compound containing a biphenylnitrile group, characterized in that: The compound is selected from the compounds of general formula (1), In the formula, P1 and P2 each independently represent a polymerizable group; L1 and L2 each independently represent an alkylene group having 1 to 30 carbon atoms; the alkylene group may be linear or branched; one or more -CH2- in the alkylene group may be replaced by -O-, -S-, -NH-, -NR a -, -CO-, -OCO-, -COO-, -OCOO-, -SCO-, -COS-substituted; A1 and A2 each independently represent One or more of the groups consisting of; Z1 and Z2 each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -OCOO-, -CH2O-, -OCH2-, -CF2O-, and -OCF2-; x and y each independently represent an integer of 1 to 3; R1-R2 and R a Each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a halogen group having 1 to 30 carbon atoms alkyloxycarbonyl having 1 to 30 carbon atoms, alkylaryl having 6 to 30 carbon atoms, arylalkyl having 6 to 30 carbon atoms, alkylaryloxy having 6 to 30 carbon atoms, arylalkyloxy having 6 to 30 carbon atoms, arylcarbonyl having 6 to 30 carbon atoms, aryloxycarbonyl having 6 to 30 carbon atoms, arylcarbonyloxy having 6 to 30 carbon atoms, and aryloxycarbonyloxy having 6 to 30 carbon atoms; One or more -CH2- in the alkyl, alkoxy, alkenyl, alkenyloxy group may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl, alkenyloxy group may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, alkyl having 1 to 30 carbon atoms, haloalkyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, haloalkoxy having 1 to 30 carbon atoms, alkylacyloxy having 1 to 30 carbon atoms, haloalkylacyloxy having 1 to 30 carbon atoms, or a polymerizable group; k each independently represents an integer of 0-10; m and p each independently represent an integer of 0-4; n represents an integer of 0-3; when k, m, n and p≥2, multiple R1s and R2s may be the same or different.

2. The polymerizable compound according to claim 1, wherein The polymerizable group is selected from the following groups: Wherein, R3 has the same definition as R1-R2.

3. The polymerizable compound according to claim 2, characterized in that 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).

4. The polymerizable compound according to claim 1, characterized in that L1 and L2 each independently represent an alkylene group having 1 to 16 carbon atoms.

5. The polymerizable compound according to claim 1, characterized in that , , x and y represent 2.

6. The polymerizable compound according to claim 1, characterized in that ,, k, m, n and p all represent 0.

7. The polymerizable compound according to claim 1, characterized in that , the compound is selected from the compounds of general formula (2), in, P1 and P2, L1 and L2, R1 and R2 as well as k, m, n and p are as defined in the general formula (1).

8. A polymerizable liquid crystal composition, characterized in that: The method comprises the polymerizable compound according to any one of claims 1 to 7.

9. An optically anisotropic body, characterized in that: The polymerizable liquid crystal composition according to claim 8 is used.

10. The optically anisotropic body according to claim 9, wherein The optical anisotropic body is selected from negative dispersion optical films.

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