WO2025044373A1 - Negative dispersion optical film and compound - Google Patents

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 Coatings and Compounds Technical Field

The invention belongs to the technical field of light regulation, and in particular relates to a negative dispersion optical film and a compound.

Background Art

Polymerizable compounds (RM) are becoming more and more widely valued as raw materials for preparing various optical anisotropic bodies. In the prior art, RM solutions are usually coated on substrates to align them, and then heated or irradiated with active energy rays to cure them, thereby forming an optically anisotropic polymer film with uniform orientation, also known as an optically anisotropic body. The orientation of the film can be planar (the liquid crystal molecules are basically parallel to the layer orientation), homeotropic (rectangular or perpendicular to the layer) or inclined, or it can be cholesteric oriented.

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

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 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, elliptically polarizing elements, and various other optical elements.

In the example of negative dispersion optical film, it is necessary to add a polymerizable compound to the matrix liquid crystal to obtain a polymerizable liquid crystal composition, thereby reducing the wavelength dispersion of its birefringence and effectively improving the display performance. However, the negative dispersion optical film in the prior art is prone to yellowing and uneven orientation.

Therefore, it is required to develop a polymerizable compound whose use can solve the above-mentioned technical problems.

Summary of the invention

The object of the present invention is to provide a polymerizable compound containing biphenylnitrile groups and an optical film application thereof. The optical anisotropy formed by the polymerizable compound described above and below is excellent in orientation non-uniformity and also significantly improves the yellowing performance under ultraviolet light.

The inventors have made great efforts to study the molecular engineering of polymerizable compounds according to the "function-synthesis-structure" concept, and found that the above-mentioned 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.

The present invention comprises the following structures:

A polymerizable compound containing a biphenylnitrile group, wherein the compound is selected from compounds of the 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 substituted by -O-, -S-, -NH-, _-NRa- , -CO-, -OCO-, -COO-, -OCOO-, -SCO-, or -COS-;

_A1 and _A2 each independently represent One or more of the groups consisting of;

Z ₁ and Z ₂ each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -OCOO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, and -OCF ₂ -;

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

R1 _{to R2} and _Ra each independently represent 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, 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, a haloalkylacyloxy group having 1 to 30 carbon atoms, an alkylaryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryloxy group having 6 to 30 carbon atoms, an arylalkyloxy group having 6 to 30 carbon atoms, an arylcarbonyl group having 6 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, an arylcarbonyloxy group having 6 to 30 carbon atoms, and an aryloxycarbonyloxy group having 6 to 30 carbon atoms; one or more -CH ₂ - may be substituted by -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; optionally, one or more H atoms in the alkyl, alkoxy, alkenyl, alkenyloxy may be substituted by halogen, halogen, cyano, hydroxyl, nitro, carboxyl, carbamoyloxy, amino, sulfamoyl, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, sulfhydryl, substituted with a halogenated isocyano 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 alkylacyloxy group having 1 to 30 carbon atoms, a haloalkylacyloxy group 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 _R1 and _R2 may be the same or different.

As the polymerizable compound described above and below, the carbon number of alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, alkylacyloxy or haloalkylacyloxy group (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 other subranges and combinations thereof; the carbon number of alkenyl, haloalkenyl, alkenyloxy and 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 other subranges and combinations thereof.

As the compound described above, wherein the polymerizable group is selected from the following groups:

In the formula, R ₃ has the same definition as R ₁ -R ₂ .

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.

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).

In a specific embodiment, _P1 and _P2 each independently represent an acrylate group.

As the polymerizable compound described above, 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-.

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- in the alkylene group may be substituted by -O- or -CO-.

More preferably, L ₁ and L ₂ each independently represent an alkylene group having 2 to 10 carbon atoms.

More preferably, _L1 and _L2 each independently represent an alkylene group having 3 to 8 carbon atoms.

Most preferably, _L1 and _L2 each independently represent an alkylene group having 4 to 6 carbon atoms.

As the polymerizable compound described above and below, wherein _Z1 and _Z2 each independently represent one or more selected from the group consisting of a single bond, -OCO-, -COO-, _-CH2O- , _-OCH2- , _-CF2O- , and _-OCF2- .

Preferably, Z ₁ and Z ₂ each independently represent one or more of the group consisting of -OCO-, -COO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, and -OCF ₂ -.

More preferably, Z ₁ and Z ₂ each independently represent one or more selected from the group consisting of -OCO-, -COO-, -CH ₂ O-, and -OCH ₂ -.

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.

As the polymerizable compound described above and below, wherein R ₁ to _{R 2} and _Ra each independently represent 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; and one or more -CH ₂ - in the alkyl group, alkoxy group, alkenyl group, or alkenyloxy group may be substituted with -O-, -S-, -CO-, -OCO-, or -COO-.

Preferably, R ₁ -R ₂ and _Ra each independently represent 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 -CH ₂ - in the alkyl group or alkoxy group may be substituted by -O- or -S-.

More preferably, R ₁ to _{R 2} and _Ra each independently represent an alkyl group having 2 to 20 carbon atoms or an alkoxy group having 2 to 20 carbon atoms.

More preferably, R ₁ to _{R 2} and _Ra each independently represent an alkyl group having 3 to 15 carbon atoms or an alkoxy group having 3 to 15 carbon atoms.

Most preferably, R ₁ to _{R 2} and _Ra each independently represent an alkyl group having 4 to 10 carbon atoms or an alkoxy group having 4 to 10 carbon atoms.

As the polymerizable compound described above and below, wherein _Ra each 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.

Preferably, Ra _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.

More preferably, _Ra 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.

More preferably, _Ra each independently represents a hydrogen atom, a halogen, a cyano group, a methyl group, a trifluoromethyl group, a methoxy group, or a trifluoromethoxy group.

Most preferably, _Ra each independently represents a hydrogen atom.

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.

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.

More preferably, k, m, n and p all represent zero.

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

in,

P1 and _P2 , _L1 and _L2 , _R1 and _R2 , and k, m, n and p are as defined in _the general formula (1).

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

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

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

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

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.

The polymerizable liquid crystal composition as described above and below optionally further contains additives.

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, deaerators, diluents, thixotropic agents, gelling agents, catalysts, metals, metal complexes, luminescent materials, and the like.

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.

The polymerizable liquid crystal composition as described above and below further includes an organic solvent.

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 less.

The organic solvent is not particularly limited, but preferably an organic solvent in which the polymerizable liquid crystal composition shows good solubility, preferably an aromatic solvent such as toluene, xylene, cumene, 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.; tetrahydrothiophene, 1,2-dimethoxyethane, benzene, etc. Ether solvents such as methyl ether, amide solvents such as N,N-dimethylformamide and N-methyl-2-pyrrolidone; propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone and chlorobenzene, etc.

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

Based on the consideration of solution stability, it is preferred to use one or more of ketone solvents, ether solvents, ester solvents and aromatic solvents.

As the polymerizable liquid crystal composition described in the context, 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.

When preparing the polymerizable liquid crystal composition solution, heating and/or stirring are advantageously performed in order to promote dissolution of the polymerizable liquid crystal composition.

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

The coating method includes, but is not limited to, an applicator method, a rod 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, a dipping method, etc. After coating the polymerizable liquid crystal composition, it is cured (dried).

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

The substrate of the solidified material includes, but is not limited to, a glass substrate, a metal substrate, a ceramic substrate, a polymer substrate. Further, as the polymer substrate, for example, it can be: a cellulose derivative, a polyolefin, a polyester, a polyolefin, a polycarbonate, a polyacrylate, a polyarylate, a polyether sulfone, a polyamide, a polyimide, a polyphenylene sulfide, a polyphenylene oxide or a polystyrene, etc.

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

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

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.

The materials of the alignment film include, but are not limited to, polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene oxide, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, acrylic resin, epoxy acrylic resin, coumarin, chalcone, cinnamate, anthraquinone, azo compound, aryl vinyl compound, etc. Based on the process applicability, especially based on the consideration of heat resistance and chemical stability, polyimide is preferred.

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.

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

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, visual enlargement films, reflective films, selective reflective films, anti-reflective films, brightening films, liquid crystal orientation films, polarizing films (deflecting plates), polarizing elements, circular polarizing elements, and elliptically polarizing elements.

Preferably, the application is a negative dispersion optical film.

The negative dispersion optical film described above has excellent orientation malalignment and significantly improves yellowing performance under ultraviolet light. Therefore, each compound described above can be used as a component of a polymerizable composition. In addition, an optically anisotropic body using a polymerizable liquid crystal composition containing the compound of the present invention can be used for optical films and the like.

DETAILED DESCRIPTION

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

The term "liquid crystal" or "mesogenic compound" refers to a compound which forms a mesomorphic phase or a liquid crystal phase under certain conditions.

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

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

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

The term "film" refers to a rigid or flexible coating or layer having mechanical stability; optionally, the film can be alone; located on a supporting substrate; or sandwiched between two substrates.

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 percentage.

Synthesis Example

Synthesis of the compound P of the present invention.

The synthetic route of compound P is as follows:

Preparation of intermediate S-3

40 g of compound S-1 and 53.2 g of compound S-2 were added to a 500 ml reaction bottle. Add 400g of dichloromethane and 5.4g of DMAP. Then cool to 0°C, and add a dichloromethane solution of DCC (50g dissolved in 120g of dichloromethane) dropwise. After the addition is complete, heat to 25°C and react for 12h. Post-treatment: first filter with suction, wash the filter cake with dichloromethane, retain the liquid phase, wash the reaction liquid with 200g of 5% hydrochloric acid, and then wash twice with 200g of water. Dry, pass the organic phase through a silica gel column, add 0.07g of p-methoxyphenol to the eluent, then desolventize under reduced pressure, and recrystallize with 800g of methanol and 80g of dichloromethane. Obtain 70g of intermediate S-3 with a yield of 80%.

Preparation of intermediate S-4

Take 70g of intermediate S-3 and add it to a 1000ml three-necked flask, add 200ml of dichloromethane, 13.9g of hydrogen peroxide, 0.5g of 4-OH-TEMPO, 2.4g of sodium dihydrogen phosphate and 200g of water. Heat to 35°C, add sodium chlorite aqueous solution (12.9g dissolved in 150g of water), add dropwise, and keep warm for 2h. Filter the reaction solution to obtain a solid. Pulp with 200g of isopropanol, then filter and dry to obtain 64.6g of intermediate S-4, with a yield of 94%.

Preparation of Product P

Add 60g of intermediate S-4 and 14g of compound S-5 to a 500ml reaction bottle, add 300g of dichloromethane and 2g of DMAP, then cool to 0℃, and add a dichloromethane solution of DCC (16g dissolved in 60g of dichloromethane) dropwise. After the addition is complete, heat to 25℃ and react for 12h. Post-treatment, first filter, wash the filter cake with dichloromethane, retain the liquid phase, wash the reaction liquid with 100g of 5% hydrochloric acid, and then wash twice with 100g of water. Dry, pass the organic phase through a silica gel column, add 0.1g of p-methoxyphenol to the eluent, then desolventize under reduced pressure, and recrystallize with 600g of methanol and 60g of dichloromethane. 59g of product P is obtained with a yield of 82%.

The nuclear magnetic resonance data are as follows: ¹ H NMR (CDCl ₃ )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).

Example 1 and Comparative Examples 1-3

Example 1 uses compound P of the present invention.

Comparative Examples 1-3 used known compounds B-1 to B-3 from the prior art.

In order to evaluate the non-uniform orientation performance and yellowing performance of the negative dispersion optical film, a liquid crystal composition as a mother liquid crystal (M) was provided. The liquid crystal composition contained 50% of the Compound (M-1), 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.

The polyimide solution for the 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.

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

The coating solution was applied to the rubbed alignment film by spin coating, dried at 80°C for 1 minute and further dried at 120°C for 1 minute, and then irradiated with ultraviolet light at an intensity of 40 mW/cm ² for 25 seconds using a high pressure mercury lamp to prepare a negative dispersion optical film to be evaluated.

The degree of unevenness of the obtained negative dispersion optical film was evaluated by observation under a polarizing microscope. Ten negative dispersion optical films to which the compound to be evaluated was added were prepared, and the number of unevenness was counted. The number of unevenness observed in the 10 negative dispersion optical films was totaled, and if the number of unevenness was 0, it was recorded as excellent, if the number of unevenness was 1, it was recorded as good, if the number of unevenness was 1-10, it was recorded as medium, and if the number of unevenness was more than 10, it was recorded as poor.

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

Yellowing performance is evaluated using the yellowness index (YI). The difference (△YI) between the YI value before the sun exposure test and the YI value after the sun exposure test is calculated. The yellowness index (YI) is measured using a JASCO UV/VIS spectrophotometer V-560 and calculated using the included color diagnostic program. The calculation formula is: YI = 100 (1.28X-1.06Z)/Y (JIS K7373) (X, Y, Z represent the three stimulus values in the XYZ color system. The smaller the △YI value, the less discoloration.

Table 1

Table 2

As can be seen from Table 2, the negative dispersion optical film of Example 1 has excellent orientation malalignment and significantly improves the yellowing performance under ultraviolet light. Therefore, the compound of the present invention can be used as a component of a polymerizable composition. In addition, an optical anisotropic body using a polymerizable liquid crystal composition containing the compound of the present invention can be used for negative dispersion optical films, etc.

It should be understood that the specific embodiments of the present invention are only used to illustrate the spirit and principles of the present invention, and are not used to limit the scope of the present invention. In addition, it should be understood that after reading the content of the present invention, those skilled in the art can make various changes, substitutions, deletions, corrections or adjustments to the technical solutions of the present invention, and these equivalent technical solutions also fall within the scope defined by the claims of the present invention.

Claims (10)

A polymerizable compound containing a biphenylnitrile group, characterized in that the compound is selected from 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 substituted by -O-, -S-, -NH-, _-NRa- , -CO-, -OCO-, -COO-, -OCOO-, -SCO-, or -COS-; _A1 and _A2 each independently represent One or more of the groups consisting of; Z ₁ and Z ₂ each independently represent one or more of the group consisting of a single bond, -OCO-, -COO-, -OCOO-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, and -OCF ₂ -; x and y each independently represent an integer of 1 to 3; R ₁ to R ₂ and _Ra each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a halogen group having 1 to 30 carbon atoms, alkyl, alkyloxy, alkylcarbonyl, alkylcarbonyl, alkylcarbonyl, alkylcarbonyl, alkylacyloxy, alkyloxy, alkylcarbonyl, alkylacyloxy, alkyloxy, alkylcarbonyl, alkyloxy, alkyloxycarbonyl ... a halogenated alkylacyloxy group having 1 to 30 carbon atoms, an alkylaryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryloxy group having 6 to 30 carbon atoms, an arylalkyloxy group having 6 to 30 carbon atoms, an arylcarbonyl group having 6 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, an arylcarbonyloxy group having 6 to 30 carbon atoms, and an aryloxycarbonyloxy group having 6 to 30 carbon atoms; one or more -CH ₂ - 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 _R1 and _R2 may be the same or different. The polymerizable compound according to claim 1, wherein the polymerizable group is selected from the following groups:
In the formula, R ₃ has the same definition as R ₁ -R ₂ . 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). The polymerizable compound according to claim 1, wherein _L1 and _L2 each independently represent an alkylene group having 1 to 16 carbon atoms. The polymerizable compound according to claim 1, characterized in that x and y represent 2. The polymerizable compound according to claim 1, wherein k, m, n and p all represent 0. 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 , and k, m, n and p are as defined in _the general formula (1). A polymerizable liquid crystal composition, characterized in that it comprises the polymerizable compound according to any one of claims 1 to 7. An optically anisotropic body, characterized in that it is formed from the polymerizable liquid crystal composition according to claim 8. The optically anisotropic body according to claim 9, wherein the optically anisotropic body is selected from negative dispersion optical films.