Liquid crystal compound, liquid crystal composition and phase difference film

Abstract

The invention provides a liquid crystal compound, a liquid crystal composition and a phase difference film, relates to the technical field of optical material preparation, and particularly provides a polymerizable liquid crystal compound for forming a phase difference film with excellent reverse wavelength dispersibility and reliability. The invention also provides a liquid crystal composition containing the liquid crystal compound provided by the invention and a phase difference film formed by polymerizing the liquid crystal composition. By using the liquid crystal compound provided by the invention, the phase difference film with excellent reverse wavelength dispersibility, excellent reliability and fewer alignment defects can be prepared.

Description

Technical Field

[0001] The present application relates to the technical field of optical material preparation, and in particular to a liquid crystal compound, a liquid crystal composition, and a phase difference film. Background Art

[0002] Optical films are a key component in modern display technology, influencing performance such as display brightness, clarity, and color skew within a wide viewing angle. Retardation films with reverse wavelength dispersion, due to their unique optical properties, are widely used in polarizers for liquid crystal displays (LCDs) and organic light-emitting diode displays (OLEDs) for anti-reflection and viewing angle compensation. Retardation generally refers to the proportional relationship between the phase difference and wavelength at a normal viewing angle. This is typically expressed as the phase difference (R450) at a wavelength of 450 nm and the phase difference (R550) at a wavelength of 550 nm satisfying the following condition: R450 / R550 < 1.0.

[0003] Retardation films that achieve reverse wavelength dispersion currently primarily utilize liquid crystal polymers, which exploit the material's birefringence to create phase difference. These liquid crystal polymers typically use a composition coating solution as a precursor. This precursor contains one or more polymerizable liquid crystal compounds, an initiator, and a solvent. To achieve a specific orientation of the liquid crystals, the substrate on which they are supported must have a functional alignment layer. After the precursor solution is applied to the substrate containing the alignment layer and then heated and dried, the solvent evaporates. Under certain temperature conditions, the liquid crystal compounds form a liquid crystal phase with a specific orientation (i.e., "alignment"). Subsequently, ultraviolet light is used to initiate polymerization, fixing the alignment of the liquid crystals. This results in an anisotropic polymer film with a well-regarded orientation and the optical properties of phase difference, known as a retardation film.

[0004] Therefore, extensive research has been conducted on polymerizable liquid crystal compounds or polymerizable compositions containing such compounds capable of forming retardation films with reverse wavelength dispersion. Existing polymerizable liquid crystal compounds with reverse wavelength dispersion typically employ a T-type molecular design (reference patents: CN101838264B, CN101379420B, CN107001242B, CN109952323B, CN105384723B, etc.). However, these compounds or compositions containing them suffer from numerous issues, including insufficient reverse wavelength dispersion, poor solubility, high manufacturing costs, poor film-forming reliability, and numerous film alignment defects. Summary of the Invention

[0005] In order to solve the problems that the liquid crystal compound structures disclosed in the prior art generally have only one chromophore side chain, fewer chromophores, and higher R450 / R550 values, i.e., insufficient reverse wavelength dispersibility; these liquid crystal compound structures have fewer polymerizable groups and lower cross-linking completion, which is not conducive to the reliability of the system, for example, the optical properties of the optical film change after high temperature; and the compositions containing these liquid crystal compounds are prone to alignment defects during the film formation process, according to the first aspect of the present application, a polymerizable liquid crystal compound for forming a phase difference film with excellent reverse wavelength dispersibility and reliability is provided, and the structural formula of the liquid crystal compound is shown in the following formula (I): L 1 -SP 1 -C 1 -Ar 1 -M 1 -B 1 -M 2 -Ar 2 -M 3 -B 2 -M 4 -Ar 3 -C 2 -SP 2 -L 2 (1) In formula (1), Ar 2 is selected from the following groups represented by formula (Ar-1) to formula (Ar-3), Ar 1 and Ar 3 Each is independently selected from the group represented by the following formula (Ar-1) or formula (Ar-2), * represents the bonding position,

[0006] In formulae (Ar-1) to (Ar-3), Q is selected from a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms. V 1 、V 2 、V 3 and V 4 each independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a sulfur pentafluoride group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or a thioisocyano group, W 1 Selected from 、 、 、 、 、 、 or , W 1 The hydrogen atoms at any position on the aromatic ring may be substituted by one or more substituents U, wherein U is selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a sulfur pentafluoride group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group or a thioisocyano group, W 2 As shown in the following formula (W-1), J 1 -T 1 -* (W-1) In formula (W-1), T 1 A linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- groups are independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, J 1 is selected from a hydrogen atom or a polymerizable group, wherein the polymerizable group is selected from the group represented by the following formula (J-1) or formula (J-2),

[0007] M 1 、M 2 、M 3 and M 4Each independently selected from -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=CH -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO- CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF- or -C≡C-, B 1 and B 2 are each independently selected from the groups represented by the following formulae (B-1) to (B-5),

[0008] C 1 and C 2 Each independently selected from a single bond, -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=C H-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO- CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF- or -C≡C-, SP 1 and SP 2Each is independently selected from a linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- groups are independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, L 1 and L 2 Each is independently selected from a hydrogen atom or a polymerizable group, and the polymerizable group is selected from the group represented by the above formula (J-1) or formula (J-2).

[0009] Optionally, Ar 2 It is selected from the group represented by formula (Ar-1) or formula (Ar-2).

[0010] Optionally, J 1 It is selected from the group represented by formula (J-1) or formula (J-2).

[0011] Optionally, L 1 and L 2 Each is independently selected from the group represented by formula (J-1) or formula (J-2).

[0012] Optionally, the liquid crystal compound is selected from the following structures:

[0013]

[0014]

[0015]

[0016]

[0017]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033] .

[0034] According to the second aspect of the present application, a liquid crystal composition is provided, comprising the liquid crystal compound according to the first aspect of the present application.

[0035] Optionally, the liquid crystal composition further comprises a polymerizable compound; The polymerizable compound is selected from the following structures:

[0036] .

[0037] Optionally, the liquid crystal composition comprises 50 to 100 parts of the liquid crystal compound and 0.1 to 50 parts of the polymerizable compound, in parts by weight.

[0038] According to a third aspect of the present application, a phase difference film is provided. The phase difference film is formed by polymerizing the liquid crystal composition described in the second aspect of the present application.

[0039] Optionally, a phase difference R450 of the phase difference film at a wavelength of 450 nm and a phase difference R550 at a wavelength of 550 nm satisfy the relationship: R450 / R550<1.0.

[0040] The technical solution adopted by the present invention can achieve the following beneficial effects: This application provides a polymerizable liquid crystal compound for forming a retardation film with excellent reverse wavelength dispersion and reliability. Furthermore, the use of a polymerizable composition containing the polymerizable liquid crystal compound provided herein can suppress the generation of alignment defects during the retardation film manufacturing process. Thus, by using the liquid crystal compound provided herein, a retardation film with excellent reverse wavelength dispersion, excellent reliability, and fewer alignment defects can be produced. DETAILED DESCRIPTION

[0041] To make the objectives, technical solutions, and advantages of the present invention more clear, the technical solutions of the present invention will be clearly and completely described below in conjunction with specific embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0042] Through research on the prior art, the inventors of this application have found that the liquid crystal compounds in the prior art usually have the following problems: 1. The disclosed compound structures usually have only one chromophore side chain, with fewer chromophores and higher R450 / R550 values, that is, insufficient reverse wavelength dispersion; 2. The structures of these compounds have fewer polymerizable groups and a low degree of cross-linking, which is not conducive to the reliability of the system. For example, the optical properties of the optical film change after being exposed to high temperatures; 3. Alignment defects are prone to occur during the film formation process of the compositions containing these compounds.

[0043] To address the aforementioned issues in the prior art, the inventors of this application conducted in-depth research and discovered that when a polymerizable liquid crystal compound has multiple chromophoric side chains spaced a certain distance apart, each containing a polymerizable group (e.g., acrylate), the compound exhibits excellent reverse wavelength dispersion and reliability after film formation. This polymerizable liquid crystal compound is less likely to cause alignment defects during the manufacture of retardation films.

[0044] In one embodiment, the present application provides a polymerizable liquid crystal compound.

[0045] [Polymerizable liquid crystal compound] The polymerizable liquid crystal compound of the present invention has a structure represented by formula (1).

[0046] L 1 -SP 1 -C 1 -Ar 1 -M 1 -B 1 -M 2 -Ar 2 -M 3 -B 2 -M4 -Ar 3 -C 2 -SP 2 -L 2 (1) In formula (1), Ar 2 is selected from aromatic rings represented by the following formulae (Ar-1) to (Ar-3), Ar 1 and Ar 3 Each is independently selected from aromatic rings represented by the following formula (Ar-1) or formula (Ar-2), and * represents a bonding position.

[0047]

[0048] From the perspective of improving the reverse wavelength dispersion and reliability of the retardation film, Ar 2 Selected from formula (Ar-1) or formula (Ar-2).

[0049] In the above formulae (Ar-1) to (Ar-3), Q is selected from a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0050] V 1 、V 2 、V 3 and V 4 Each is independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a sulfur pentafluoride group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group or a thioisocyano group.

[0051] W 1 Selected from 、 、 、 、 、 、 or , W 1 The hydrogen atoms at any position on the aromatic ring may be substituted with one or more substituents U, wherein U is selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoride sulfur group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group or a thioisocyano group. From the perspective of ease of raw material availability and ease of synthesis, W is preferably 1 Selected from or .

[0052] W 2 It is represented by the following formula (W-1): J 1 -T 1 -* (W-1) In formula (W-1), T 1 A linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- groups can be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-. From the perspective of improving the reverse wavelength dispersion and reliability of the retardation film, T 1 Selected from -CH2CH2OCH2CH2OCH2CH2-.

[0053] J 1 is selected from a hydrogen atom or a polymerizable group, and the polymerizable group is selected from a group represented by the following formula (J-1) or formula (J-2): .

[0054] From the perspective of improving the reliability of the phase difference film, as a preferred embodiment, J 1 It is selected from the group represented by formula (J-1) or formula (J-2).

[0055] M 1 、M 2 、M 3 and M 4Each independently selected from -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=CH -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF- or -C≡C-. From the viewpoint of liquid crystallinity and ease of synthesis, M is preferably 1 、M 2 、M 3 and M 4 Each is independently selected from -OCH2-, -CH2O-, -COO-, -OCO- or -O-CO-O-.

[0056] B 1 and B 2 Each is independently selected from the groups represented by the following formula (B-1) to formula (B-5).

[0057]

[0058] From the perspective of ease of raw material acquisition and ease of synthesis, B is preferred. 1 and B 2 Each independently selected from or .

[0059] C 1 and C 2Each independently selected from a single bond, -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=C H-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO- CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF- or -C≡C-.

[0060] SP 1 and SP 2 Each is independently selected from a straight-chain or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- can be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-.

[0061] L 1 and L 2 Each is independently selected from a hydrogen atom or a polymerizable group, and the polymerizable group is selected from the group represented by the above formula (J-1) or formula (J-2).

[0062] From the perspective of improving the reliability of the phase difference film, as a preferred embodiment, L 1 and L 2 Each is independently selected from the group represented by formula (J-1) or formula (J-2).

[0063] Specifically, the compound represented by the formula (1) is preferably a compound represented by the following formula (R-1) to formula (R-22).

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] .

[0086] The method for producing the compound represented by formula (1) of the present invention is not particularly limited, and the compound can be produced by appropriately combining known organic synthesis reactions described in Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, etc. (e.g., nucleophilic substitution reaction, esterification reaction, condensation reaction, Schiff base formation reaction, deprotection reaction, etc.) according to its structure.

[0087] According to another embodiment of the present application, a liquid crystal composition comprising the above-mentioned liquid crystal compound is also provided. The liquid crystal composition is also referred to as a "polymerizable composition" in the present invention. The "polymerizable composition" will be described in detail below.

[0088] [Polymerizable composition] The polymerizable composition of the present invention contains the aforementioned polymerizable liquid crystal compound and may contain other polymerizable compounds described below, a photopolymerization initiator, a stabilizer, other auxiliary agents, a solvent, and the like in addition to the polymerizable liquid crystal compound of the present invention.

[0089] [Other polymerizable compounds] In addition to the aforementioned polymerizable liquid crystal compounds of the present invention, the polymerizable composition of the present invention may also contain other polymerizable compounds that do not exhibit reverse wavelength dispersion, which can play a role in adjusting wavelength dispersion, increasing crosslinking density, adjusting refractive index, inducing chiral phases, and reducing costs. Specifically, the polymerizable compounds represented by the following formulas (N-1) to (N-12) are preferred:

[0090] .

[0091] In one embodiment, the liquid crystal composition comprises 50 to 100 parts of the liquid crystal compound and 0.1 to 50 parts of the polymerizable compound. For example, in the liquid crystal composition of the present invention, the weight of the liquid crystal compound is 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts, 80 parts, 85 parts, 90 parts, 95 parts, 100 parts, or any value therebetween; and the weight of the polymerizable compound is 0.1 parts, 0.5 parts, 1 parts, 5 parts, 10 parts, 15 parts, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, or any value therebetween.

[0092] [Photopolymerization initiator] In order to form a cross-linked network by photoinitiated polymerization, a photopolymerization initiator generally needs to be added to the polymerizable composition. Examples of photopolymerization initiators suitable for the present invention include benzophenones, acetophenones, benzil ketals, and the like. In addition, some brand initiators such as BASF OXE-01, OXE-02, OXE-03, OXE-04, and OXE-05 can be added as photopolymerization initiators. One photopolymerization initiator can be used, or two or more photopolymerization initiators can be used simultaneously. Relative to the polymerizable composition provided in the present application, the photopolymerization initiator accounts for 0.1% to 10% by mass of the total mass of the polymerizable composition, preferably 0.2% to 8% by mass, and more preferably 1% to 7% by mass, in terms of mass fraction.

[0093] [Stabilizer] To improve storage stability, the polymerizable composition generally requires the addition of a stabilizer. Suitable stabilizers for use in the present invention include, for example, hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, and nitroso compounds. The amount of stabilizer added, when used, is preferably 0.005 to 1% by mass, more preferably 0.01 to 0.8% by mass, and even more preferably 0.02 to 0.5% by mass, relative to the total mass of the polymerizable composition. A single stabilizer may be used, or two or more stabilizers may be used simultaneously. 2,6-di-tert-butyl-p-cresol (BHT) is a preferred stabilizer.

[0094] [Other additives] In the actual coating production process, other additives may be added as needed to ensure solution leveling, photocrosslinking efficiency, and other factors. For example, additives suitable for the composition of the present invention may include a combination of one or more leveling and defoaming agents and chain transfer agents. The leveling and defoaming agent may be at least one of BYK-300, BYK-306, BYK-358, BYK-354, BYK-515, BYK-3560, and BYK-3566 available from BYK; MEGAFACE F-554 and F-556 available from DIC; and Zonyl FS-520 and Zonyl 8857A available from DuPont. When used, the additive is preferably added in an amount of 0.005% to 5% by mass, more preferably 0.01% to 3% by mass, and even more preferably 0.02% to 1% by mass, relative to the total mass of the polymerizable composition.

[0095] [Solvent] In the actual coating production process, solvents are needed to assist in the coating process. The solvents suitable for the composition of the present invention mainly include benzenes, ketones, ethers, esters, halogenated hydrocarbons and highly polar solvents. Benzene solvents mainly include: toluene, ethylbenzene, xylene, chlorobenzene, anisole; ketone solvents mainly include: acetone, methyl ethyl ketone, 3-pentanone, cyclopentanone, cyclohexanone, isophorone; ether solvents mainly include: 1,4-dioxane, tetrahydrofuran; ester solvents mainly include: ethyl acetate, butyl acetate, propylene glycol methyl ether acetate; halogenated hydrocarbon solvents mainly include: dichloromethane, chloroform, 1,2-dichloroethane; highly polar solvents mainly include: methanol, ethanol, isopropanol, n-butanol, tert-butanol, propylene glycol methyl ether, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethyl-2-pyrrolidone, ethanolamine, acetonitrile. One solvent may be used alone, or two or more solvents may be used simultaneously.

[0096] [Phase difference film] The retardation film of the present invention is formed by polymerizing the polymerizable composition of the present invention. The retardation film has a retardation value R450 at a wavelength of 450 nm and a retardation value R550 at a wavelength of 550 nm that satisfies the following condition: R450 / R550<1.0.

[0097] Example The present invention will be further described below with reference to specific examples, but the present invention is not limited to the following examples.

[0098] Example 1 Production of compounds represented by formula (R-2)

[0099] Methyl trans-4-[(methylsulfonyloxy)methyl]cyclohexanecarboxylate (5 g, 20 mmol), hydroquinone (1.1 g, 10 mmol) and cesium carbonate (9.8 g, 30 mmol) were dissolved in 60 mL of anhydrous N,N The reaction mixture was reacted with dimethylformamide at 100°C for 24 hours. The reaction solution was poured into 200 mL of water and extracted three times with ethyl acetate. The organic phases were combined and concentrated, and the resulting mixture was purified by column chromatography and recrystallization to obtain 4.8 g of compound R-2a as a white solid in a yield of 58%.

[0100] Compound R-2a (4.8 g, 11.5 mmol) was dissolved in 80 mL of methanol. 23 mL of 2M aqueous sodium hydroxide solution was added dropwise at room temperature and allowed to react at 50°C for 4 hours. The methanol was removed by concentration under reduced pressure. 100 mL of water was added, and 3M hydrochloric acid was added dropwise in an ice-water bath for neutralization. The mixture was filtered and the filter cake was dried to obtain 4 g of compound R-2b as a white solid (89% yield).

[0101] Compound R-2b (4 g, 10.3 mmol), 2,5-dihydroxybenzaldehyde (3.1 g, 22.6 mmol), and 4-dimethylaminopyridine (0.25 g, 2.1 mmol) were dissolved in 50 mL of dichloromethane and slowly added dropwise under ice-water bath. N,N’ -Diisopropylcarbodiimide (2.8 g, 22.6 mmol) was reacted at room temperature for 6 hours. 300 mL of methanol was slowly added dropwise to the solution to crystallize. The mixture was filtered and the filter cake was dried to obtain 6.1 g of compound R-2c as a white solid in a 94% yield.

[0102] Compound R-2c (6.1 g, 9.7 mmol), potassium carbonate (8 g, 58.2 mmol), and potassium iodide (0.31 g, 1.8 mmol) were dissolved in 60 mL of anhydrous N,N To the mixture of 1,4-dimethylformamide, 6-chloro-1-hexanol (7.8 g, 57.2 mmol) was slowly added and the reaction was carried out at 60°C for 3 hours. The reaction solution was poured into 200 mL of water and extracted three times with ethyl acetate. The combined and concentrated organic phases were combined and purified by column chromatography to obtain 6 g of compound R-2d as a brown oil in a 78% yield.

[0103] Compound R-2d (6.3 g, 7.6 mmol), compound R-2e (5 g, 16.7 mmol), and glacial acetic acid (1.4 g, 22.8 mmol) were dissolved in 50 mL of chloroform and reacted at 50°C for 2 hours. The resulting mixture was concentrated under reduced pressure, and column chromatography afforded 9.6 g of compound R-2f as a brown gel, in a 91% yield.

[0104] Compound R-2f (9.6 g, 6.9 mmol) and N,N 1-Diisopropylethylamine (2.7 g, 20.7 mmol) was dissolved in 50 mL of dichloromethane. Acryloyl chloride (1.9 g, 20.7 mmol) was added dropwise under an ice-water bath. The mixture was allowed to react at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to obtain 9.3 g of compound R-2 as a white solid, with a yield of 69%. 1 H NMR (400MHz, CDCl3) δ 8.33 (s, 2H), 7.70-7.61 (m, 4H), 7.63 (d, J = 2.9 Hz, 2H), 7.36-7.30 (m, 2H), 7.19-7.12 (m, 2H), 7.02 (dd, J = 8.9, 2.9 Hz, 2H), 6.89 (d, J= 9.0Hz, 2H), 6.85 (s, 4H), 6.43-6.34 (m, 4H), 6.16-6.05 (m, 4H), 5.84-5.75 (m,4H), 4.54 (t, J = 5.6 Hz, 4H), 4.21-4.15 (m, 8H), 4.04 (t, J = 6.5 Hz, 4H), 3.88(t, J = 5.8 Hz, 4H), 3.78 (d, J = 6.2 Hz, 4H), 3.67-3.57 (m, 12H), 2.62-2.54 (m,2H), 2.32-2.23 (m, 4H), 2.12-2.04 (m, 4H), 1.91-1.81 (m, 6H), 1.71-1.60 (m,8H), 1.57-1.45 (m, 8H), 1.24-1.15 (m, 4H). Example 2 Production of compounds represented by formula (R-4)

[0105] Compound R-4a (2.5 g, 5.6 mmol), hydroquinone (0.27 g, 2.5 mmol) and 4-dimethylaminopyridine (0.06 g, 0.5 mmol) were dissolved in 50 mL of dichloromethane and slowly added dropwise under ice-water bath. N,N’ -Diisopropylcarbodiimide (0.7 g, 5.6 mmol) was reacted at room temperature for 12 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to obtain 1.8 g of white solid compound R-4b (75% yield).

[0106] Compound R-4b (1.8 g, 1.9 mmol), compound R-2e (1.2 g, 4.1 mmol), and glacial acetic acid (0.33 g, 5.6 mmol) were dissolved in 50 mL of chloroform and reacted at 40°C for 1 hour. The resulting mixture was concentrated under reduced pressure, and column chromatography and recrystallization were performed to obtain 1.8 g of compound R-4c as a white solid in a 63% yield.

[0107] Compound R-4c (1.8 g, 1.2 mmol) and N,N 1-Diisopropylethylamine (0.45 g, 3.6 mmol) was dissolved in 20 mL of dichloromethane. Acryloyl chloride (0.32 g, 3.6 mmol) was slowly added dropwise under an ice-water bath. The mixture was allowed to react at room temperature for 1 hour. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to yield 1.5 g of compound R-4 as a white solid in a 79% yield. 1 H NMR (500MHz, CDCl3) δ 8.31 (s, 2H), 7.71-7.61 (m, 6H), 7.35-7.31 (m, 2H), 7.17-7.13(m, 2H), 7.12 (s, 4H), 7.02 (dd, J = 8.9, 2.9 Hz, 2H), 6.90 (d, J = 9.0 Hz, 2H),6.43-6.35 (m, 4H), 6.16-6.06 (m, 4H), 5.84-5.76 (m, 4H), 4.53 (t, J = 5.8 Hz,4H), 4.21-4.16 (m, 8H), 4.05 (t, J = 6.5 Hz, 4H), 3.88 (t, J = 5.9 Hz, 4H), 3.68-3.59 (m, 12H), 2.68-2.59 (m, 4H), 2.38-2.29 (m, 8H), 1.90-1.82 (m, 4H), 1.77-1.68 (m, 12H), 1.55-1.45 (m, 8H). Example 3 Production of compounds represented by formula (R-7)

[0108] Compound R-7a (1.8 g, 4 mmol), tert-butylhydroquinone (0.3 g, 1.8 mmol), and 4-dimethylaminopyridine (0.044 g, 0.36 mmol) were dissolved in 40 mL of dichloromethane. Slowly add dropwise under ice-water bath. N,N’ -Diisopropylcarbodiimide (0.5 g, 4 mol) was reacted at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to obtain 1.8 g of white solid compound R-7b (98% yield).

[0109] Compound R-7b (1.8 g, 1.8 mmol), R-2e (1.1 g, 3.9 mmol), and glacial acetic acid (0.5 g, 8.8 mmol) were dissolved in 30 mL of chloroform and reacted at 50°C for 1 hour. The resulting mixture was concentrated under reduced pressure, and column chromatography and recrystallization were performed to obtain 2.5 g of compound R-7c as a white solid in a 93% yield.

[0110] Compound R-7c (2.5 g, 1.6 mmol) and N,N Dissolve diisopropylethylamine (0.6 g, 4.7 mmol) in 40 mL of dichloromethane. Add acryloyl chloride (0.4 g, 4.7 mmol) dropwise in an ice-water bath. Allow to react at room temperature for 1 hour. Concentrate under reduced pressure. The resulting mixture is purified by column chromatography and recrystallized to yield 2 g of compound R-7 as a white solid, in a 76% yield. 1 H NMR (400 MHz, CDCl3) δ 8.35 (s, 2H), 7.72-7.66 (m, 4H), 7.64 (d, J = 2.9 Hz, 2H), 7.34 (t, J =7.7 Hz, 2H), 7.17 (t, J = 7.7 Hz, 2H), 7.09 (d, J = 1.5 Hz, 1H), 7.04 (dd, J = 8.9,2.9 Hz, 2H), 6.99-6.96 (m, 2H), 6.90 (d, J = 9.1 Hz, 2H), 6.43-6.35 (m, 4H), 6.17-6.06 (m, 4H), 5.85-5.76 (m, 4H), 4.56 (t, J = 5.5 Hz, 4H), 4.21-4.15 (m,8H), 4.05 (t, J = 6.5 Hz, 4H), 3.89 (t, J = 5.8 Hz, 4H), 3.68-3.59 (m, 12H), 2.70-2.59 (m, 4H), 2.40-2.31 (m, 8H), 1.91-1.82 (m, 4H), 1.77-1.68 (m, 12H), 1.52-1.46 (m, 8H), 1.36 (s, 9H). Example 4 Production of compounds represented by formula (R-10) Compound R-10a (5 g, 12.0 mmol), 2,5-dihydroxybenzaldehyde (3.6 g, 26.4 mmol), and 4-dimethylaminopyridine (0.29 g, 2.4 mmol) were dissolved in 50 mL of dichloromethane and slowly added dropwise under ice-water bath. N,N’ -Diisopropylcarbodiimide (3.3 g, 26.4 mmol) was reacted at room temperature for 6 hours. 350 mL of methanol was slowly added dropwise to the solution for crystallization. The mixture was filtered and the filter cake was dried to obtain 7.9 g of white solid compound R-10b in a 100% yield. Compound R-10b (3.8 g, 5.8 mmol), potassium carbonate (4.8 g, 34.6 mmol), potassium iodide (0.19 g, 1.1 mmol) were dissolved in 60 mL of anhydrous N,N To the mixture of 1,4-dimethylformamide, 6-bromohexanol (6.3 g, 34.6 mmol) was slowly added and the reaction was carried out at 60°C for 3 hours. The reaction solution was poured into 200 mL of water and extracted three times with ethyl acetate. The combined and concentrated organic phases were then purified by column chromatography and recrystallization to obtain 4.8 g of compound R-10c as a brown solid in a 98% yield.

[0111] Compound R-10c (3.5 g, 4 mmol), compound R-2e (3.5 g, 13.2 mmol), and glacial acetic acid (1.2 g, 20 mmol) were dissolved in 50 mL of chloroform and reacted at 50°C for 2 hours. The resulting mixture was concentrated under reduced pressure, and column chromatography afforded 6.3 g of compound R-10d as a brown gel, in a 93% yield.

[0112] Compound R-10d (5.8 g, 3.4 mmol) and N,N 1-Diisopropylethylamine (3.5 g, 27.2 mmol) was dissolved in 50 mL of dichloromethane. Acryloyl chloride (2.4 g, 27.2 mmol) was added dropwise under an ice-water bath. The mixture was allowed to react at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and column chromatography afforded 3.1 g of compound R-10 as a pale yellow oil (47% yield). 1 H NMR (400 MHz, CDCl3) δ8.38 (s, 1H), 8.33 (s, 2H), 7.72-7.62 (m, 8H), 7.55 (d, J = 2.9 Hz, 1H), 7.33(t, J = 7.7 Hz, 3H), 7.15 (t, J= 7.9 Hz, 3H), 7.06-7.00 (m, 2H), 6.93-6.85 (m,4H), 6.43-6.33 (m, 5H), 6.16-6.03 (m, 5H), 5.84-5.72 (m, 5H), 4.59-4.50 (m,6H), 4.21-4.09 (m, 13H), 3.94-3.86 (m, 10H), 3.71-3.59 (m, 19H), 2.67-2.55(m, 2H), 2.35-2.27 (m, 4H), 2.17-2.07 (m, 4H), 2.00-1.91 (m, 2H), 1.91-1.82(m, 4H), 1.77-1.64 (m, 8H), 1.59-1.45 (m, 8H), 1.35-1.27 (m, 4H). Example 5 Production of compounds represented by formula (R-16)

[0113] Compound R-10b (3.8 g, 5.8 mmol), potassium carbonate (4.8 g, 34.6 mmol), and potassium iodide (0.19 g, 1.1 mmol) were dissolved in 60 mL of anhydrous N,N To the mixture of 2-(2-bromoethoxy)ethanol (5.9 g, 34.6 mmol) and dimethylformamide, 2-(2-bromoethoxy)ethanol (5.9 g, 34.6 mmol) was slowly added and the reaction was carried out at 60°C for 3 hours. The reaction solution was poured into 200 mL of water and extracted three times with ethyl acetate. The combined and concentrated organic phases were combined and purified by column chromatography to obtain 3.1 g of compound R-16a as a brown oil in a 64% yield.

[0114] Compound R-16a (3.1 g, 3.7 mmol), compound R-2e (3.6 g, 12.3 mmol), and glacial acetic acid (1.1 g, 18.6 mmol) were dissolved in 50 mL of chloroform and reacted at 50°C for 2 hours. The resulting mixture was concentrated under reduced pressure, and column chromatography afforded 3.5 g of compound R-16b as a brown gel, in a 56% yield.

[0115] Compound R-16b (3.5 g, 2.1 mmol) and N,N Dissolve diisopropylethylamine (2.2 g, 16.7 mmol) in 50 mL of dichloromethane. Add acryloyl chloride (1.5 g, 16.7 mmol) dropwise under an ice-water bath. Allow to react at room temperature for 2 hours. Concentrate under reduced pressure, and the resulting mixture is purified by column chromatography to yield 2.8 g of compound R-16 as a white gel (69% yield). 1H NMR (400 MHz, CDCl3)δ 8.36 (s, 1H), 8.32 (s, 2H), 7.73-7.60 (m, 8H), 7.55 (d, J = 2.8 Hz, 1H), 7.33(t, J = 7.8 Hz, 3H), 7.14 (t, J = 7.6 Hz, 3H), 7.05-7.01 (m, 2H), 6.97-6.87 (m,4H), 6.45-6.32 (m, 5H), 6.17-6.03 (m, 5H), 5.85-5.72 (m, 5H), 4.58-4.50 (m,6H), 4.38-4.32 (m, 4H), 4.24-4.15 (m, 8H), 3.93-3.80 (m, 19H), 3.71-3.59 (m,19H), 2.67-2.55 (m, 2H), 2.32-2.28 (m, 4H), 2.17-2.07 (m, 4H), 1.98-1.91 (m,2H), 1.72-1.66 (m, 4H), 1.35-1.20 (m, 4H). Example 6 Production of compounds represented by formula (R-18)

[0116] Compound R-10c (2 g, 2.3 mmol), compound R-18a (2.2 g, 7.7 mmol), and glacial acetic acid (0.7 g, 11.7 mmol) were dissolved in 50 mL of chloroform and reacted at 50°C for 1 hour. The resulting mixture was concentrated under reduced pressure, and column chromatography afforded 3.1 g of compound R-18b as a white solid in a 79% yield.

[0117] Compound 18b (3 g, 1.8 mmol) and N,N 1-Diisopropylethylamine (1.8 g, 14.2 mmol) was dissolved in 30 mL of dichloromethane. Acryloyl chloride (1.3 g, 14.2 mmol) was added dropwise under an ice-water bath. The mixture was allowed to react at room temperature for 4 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to yield 2.8 g of compound R-18 as a white solid (82% yield). 1 H NMR (400 MHz, CDCl3) δ 8.16 (s, 1H), 8.10 (s, 2H), 7.71-7.62 (m, 8H), 7.55 (d, J= 2.9 Hz,1H), 7.32 (t, J = 7.7 Hz, 3H), 7.14 (t, J = 7.2 Hz, 3H), 7.05-6.99 (m, 2H), 6.92-6.85 (m, 4H), 6.43-6.31 (m, 5H), 6.15-6.02 (m, 5H), 5.84-5.73 (m, 5H), 4.39-4.31 (m, 6H), 4.18 (t, J = 6.6 Hz, 4H), 4.13 (t, J = 6.7 Hz, 4H), 4.09-4.02 (m,6H), 3.92-3.86 (m, 4H), 2.66-2.55 (m, 2H), 2.35-2.27 (m, 4H), 2.18-2.08 (m,4H), 1.98-1.91 (m, 2H), 1.90-1.29 (m, 60H). Example 7 Production of compounds represented by formula (R-20)

[0118] Compound R-10c (2 g, 2.3 mmol), compound R-20a (2.2 g, 7.7 mmol), and glacial acetic acid (0.7 g, 11.7 mmol) were dissolved in 50 mL of chloroform and reacted at 50°C for 1 hour. The resulting mixture was concentrated under reduced pressure, and column chromatography afforded 3 g of compound R-20b as a white solid in a 78% yield.

[0119] Compound 20b (3 g, 1.8 mmol) and N,N 1-Diisopropylethylamine (1.9 g, 14.6 mmol) was dissolved in 30 mL of dichloromethane. Acryloyl chloride (1.3 g, 14.6 mmol) was added dropwise under an ice-water bath. The mixture was allowed to react at room temperature for 4 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography and recrystallized to yield 2.4 g of compound R-20 as a white solid (69% yield). 1 H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 8.31 (s, 2H), 7.72-7.58 (m, 8H), 7.55 (d, J = 2.9 Hz,1H), 7.27 (t, J = 7.7 Hz, 3H), 7.17 (t, J= 7.9 Hz, 3H), 7.04-6.98 (m, 2H), 6.93-6.85 (m, 4H), 6.45-6.36 (m, 5H), 6.18-6.05 (m, 5H), 5.86-5.74 (m, 5H), 4.59-4.49 (m, 6H), 4.28-4.19 (m, 13H), 3.95-3.86 (m, 10H), 3.75-3.60 (m, 19H), 2.68-2.55 (m, 2H), 2.35-2.28 (m, 4H), 2.18-2.07 (m, 4H), 2.00-1.90 (m, 2H),1.91-1.81 (m, 4H), 1.78-1.64 (m, 8H), 1.61-1.45 (m, 8H), 1.36-1.27 (m, 4H). Comparative Example 1 Compound represented by formula (X-1)

[0120] Comparative Example 2 Compound represented by formula (X-2)

[0121] [Preparation of Phase Difference Film] The photoalignment agent HSPA-252B (manufactured by Osaka Organic Co., Ltd.) was evenly applied to the glass surface using a spin coater (2300 rpm, 10 s). Drying was performed at 120°C. After cooling to room temperature, the surface was irradiated with 10 mJ of polarized ultraviolet light at 313 nm to obtain a glass substrate with an alignment layer. The polymerizable composition solutions described in Table 1 were evenly applied to the glass substrate with the alignment layer using a spin coater (600 rpm, 30 s), and the solvent was dried at 100°C to evaporate. The surface was then cooled to room temperature and irradiated with a mercury lamp in a nitrogen atmosphere with a total energy of 1500 mJ / cm 2 , that is, phase difference films are obtained, such as Examples 8 to 14 and Comparative Examples 3 to 4 shown in Table 2.

[0122] Table 1

[0123] [Wavelength Dispersion] The retardation of the prepared retardation film was measured at various wavelengths using an Axoscan polarimeter. The retardation at 450 nm (R450) and the retardation at 550 nm (R550) were measured. R450 / R550 was calculated and evaluated according to the following criteria. The results are shown in Table 2. A smaller R450 / R550 ratio indicates better reverse wavelength dispersion.

[0124] A: R450 / R550 is less than or equal to 0.8 B: R450 / R550 is greater than 0.8 and less than or equal to 0.85 C: R450 / R550 is greater than 0.85 and less than or equal to 0.9 D: R450 / R550 greater than 0.9 [Alignment defects] The produced retardation film was visually observed using an optical microscope to determine the number of alignment defects on the screen, and was evaluated based on the following evaluation criteria. The results are shown in Table 2 below.

[0125] A: No defects B: 1 to 10 C: 11 to 100 D: Alignment defects occur on the entire surface (>100) [Reliability] The prepared phase difference film was transferred to the linear polarizer using a pressure-sensitive adhesive and laminated in the direction of the absorption axis of the linear polarization with the slow axis of the phase difference film at 45°. The laminated composite film was placed in an 85° high-temperature test chamber, taken out after 72 hours, and cooled to room temperature. The ellipticity curve of 400-700 nm was measured using the polarization meter Axoscan to obtain the maximum wavelength of the ellipticity. The deviation values ​​of the maximum wavelength of the ellipticity of the composite film before and after the high-temperature test were compared. The results are shown in Table 2 below, where the smaller the deviation value of the maximum wavelength, the better the reliability of the phase difference film.

[0126] A: The maximum wavelength deviation is less than or equal to 5 nm B: The maximum wavelength deviation is greater than 5 nm and less than or equal to 10 nm C: The maximum wavelength deviation is greater than 10 nm and less than or equal to 15 nm D: The maximum wavelength deviation is greater than 15 nm Table 2

[0127] The results shown in Table 2 indicate that the polymerizable liquid crystal compound X-2 used in Comparative Example 4 has only one chromophore side chain, resulting in the worst reverse wavelength dispersion after film formation (wavelength dispersion rating of "D"). The polymerizable liquid crystal compound X-1 used in Comparative Example 3 has no polymerizable side chain, which detracts from the reliability of the film system after formation (reliability rating of "D").

[0128] In contrast, the polymerizable liquid crystal compounds used in Examples 8 to 10 of the present application each have two side chains, and each side chain contains both a chromophoric group and a polymerizable group (e.g., acrylate); the polymerizable liquid crystal compounds used in Examples 11 to 14 of the present application each have three side chains, and each side chain contains both a chromophoric group and a polymerizable group. This allows the phase difference films formed from the polymerizable liquid crystal compounds provided in the present application to have good reverse wavelength dispersion and reliability, while significantly improving the alignment defect problem (Examples 8 to 14). Comparing Examples 11 to 14 of the present application with Examples 8 to 10 of the present application shows that the more chromophoric groups and polymerizable groups in the side chains of the polymerizable liquid crystal compounds, the better the reverse wavelength dispersion and reliability (compared to Examples 8 to 10, Examples 11 to 14 were rated "A" for reverse wavelength dispersion and reliability).

[0129] In summary, the present invention provides a polymerizable liquid crystal compound for forming a retardation film having excellent reverse wavelength dispersion and reliability. The retardation film produced from a polymerizable composition containing the polymerizable liquid crystal compound of the present invention is less susceptible to alignment defects during the manufacturing process and exhibits excellent reverse wavelength dispersion and reliability.

[0130] The above describes the embodiments of the present application, but the present application is not limited to the above-mentioned specific implementation methods. The above-mentioned specific implementation methods are merely illustrative and not restrictive. Under the guidance of this application, ordinary technicians in this field can also make many forms without departing from the purpose of this application and the scope of protection of the claims, all of which are within the protection of this application.

Claims

1. A liquid crystal compound, characterized in that The structural formula of the liquid crystal compound is shown in the following formula (I): L 1 -SP 1 -C 1 -Ar 1 -M 1 -B 1 -M 2 -Ar 2 -M 3 -B 2 -M 4 -Ar 3 -C 2 -SP 2 -L 2 (1) In formula (1), Ar 2 is selected from the following groups represented by formula (Ar-1) to formula (Ar-3), Ar 1 and Ar 3 Each is independently selected from the group represented by the following formula (Ar-1) or formula (Ar-2), * represents the bonding position, In formulae (Ar-1) to (Ar-3), Q is selected from a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms. V 1 、V 2 、V 3 and V 4 each independently selected from a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a sulfur pentafluoride group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or a thioisocyano group, W 1 Selected from 、 、 、 、 、 、 or , W 1 The hydrogen atoms at any position on the aromatic ring may be substituted by one or more substituents U, wherein U is selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a sulfur pentafluoride group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a methoxy group, an ethoxy group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group or a thioisocyano group, W 2 As shown in the following formula (W-1), J 1 -T 1 -*(W-1) In formula (W-1), T 1 A linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- groups are independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, J 1 is selected from a hydrogen atom or a polymerizable group, wherein the polymerizable group is selected from the group represented by the following formula (J-1) or formula (J-2), M 1 、M 2 、M 3 and M 4 are each independently selected from -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF- or -C≡C- B 1 and B 2 are each independently selected from the groups represented by the following formulae (B-1) to (B-5), C 1 and C 2 Each independently selected from a single bond, -OCH2-, -CH2O-, -CO-, -COO-, -OCO-, -O-, -S-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH=CH-COO-, -CH=C H-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -COO- CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF- or -C≡C-, SP 1 and SP 2 Each is independently selected from a linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or multiple non-adjacent -CH2- groups are independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, L 1 and L 2 Each is independently selected from a hydrogen atom or a polymerizable group, and the polymerizable group is selected from the group represented by the above formula (J-1) or formula (J-2).

2. The liquid crystal compound according to claim 1, wherein Ar 2 It is selected from the group represented by formula (Ar-1) or formula (Ar-2).

3. The liquid crystal compound according to claim 1, wherein J 1 It is selected from the group represented by formula (J-1) or formula (J-2).

4. The liquid crystal compound according to claim 1, wherein L 1 and L 2 Each is independently selected from the group represented by formula (J-1) or formula (J-2).

5. The liquid crystal compound according to claim 1, wherein The liquid crystal compound is selected from the following structures: 。 6. A liquid crystal composition, characterized in that: The method comprises the liquid crystal compound according to any one of claims 1 to 5.

7. The liquid crystal composition according to claim 6, wherein The liquid crystal composition further comprises a polymerizable compound; The polymerizable compound is selected from the following structures: 。 8. The liquid crystal composition according to claim 7, wherein The liquid crystal composition comprises 50 to 100 parts of the liquid crystal compound and 0.1 to 50 parts of the polymerizable compound in parts by weight.

9. A phase difference film, characterized in that: The phase difference film is formed by polymerizing the liquid crystal composition according to any one of claims 6 to 8.

10. The phase difference film according to claim 9, characterized in that The phase difference R450 of the phase difference film at a wavelength of 450 nm and the phase difference R550 at a wavelength of 550 nm satisfy: R450 / R550<1.0.

Images