Liquid crystal compound, liquid crystal composition, and phase difference film

Abstract

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

Description

Technical Field

[0001] This application relates to the field of optical material preparation technology, and in particular to a liquid crystal compound, a liquid crystal composition, and a phase retardation film. Background Technology

[0002] Optical films are a key component in modern display technology, affecting display brightness, sharpness, and viewing angle distortion. Among them, inverse wavelength dispersion (IRD) films, due to their unique optical properties, are widely used in polarizers of liquid crystal displays (LCDs) and organic light-emitting diode (OLEDs) for anti-reflection and viewing angle compensation. IRD generally refers to the relationship between the phase difference and wavelength at a positive viewing angle. It is typically expressed as R450 at 450 nm and R550 at 550 nm satisfying the condition: R450 / R550 < 1.0.

[0003] Phase retardation films achieving reverse wavelength dispersion currently primarily utilize liquid crystal polymer materials, leveraging the material's birefringence to create a phase difference. Mainstream, these liquid crystal polymers typically use a pre-coating solution containing one or more polymerizable liquid crystal compounds, initiators, and solvents. To achieve a specific alignment of the liquid crystals, a functional alignment layer is required on the substrate. After coating the pre-coating solution onto the substrate containing the alignment layer, a heating and drying process is performed. Once the solvent evaporates, the liquid crystal compounds form a liquid crystal phase with a specific orientation (i.e., "alignment") under certain temperature conditions. Subsequently, a polymerization reaction is initiated by ultraviolet light to fix the liquid crystal alignment, resulting in a well-aligned, anisotropic polymer film with phase retardation optical properties—the phase retardation film.

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

[0005] To address the issues that existing liquid crystal compound structures typically have only one chromophore side chain, resulting in fewer chromophores and higher R450 / R550 values, indicating insufficient reverse wavelength dispersion; these liquid crystal compound structures also have fewer polymerizable groups and lower crosslinking completion, which is detrimental to system reliability, such as changes in the optical properties of optical films after high temperatures; and the tendency for alignment defects to occur during film formation in compositions containing these liquid crystal compounds, according to a first aspect of this application, a polymerizable liquid crystal compound for forming a phase retardation film with excellent reverse wavelength dispersion and reliability is provided, the liquid crystal compound having the following structural formula (I):

[0006] 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)

[0007] In equation (1), Ar 2 Selected from the groups shown in formulas (Ar-1) to (Ar-3), Ar 1 and Ar 3 Each group is independently selected from the groups shown in formula (Ar-1) or formula (Ar-2), where * indicates the bonding position.

[0008]

[0009] In formulas (Ar-1) to (Ar-3), Q is selected from straight-chain or branched alkyl groups having 1 to 20 carbon atoms.

[0010] V 1 V 2 V 3 and V 4 Each group is independently selected from hydrogen atoms, straight-chain or branched alkyl groups having 1 to 10 carbon atoms, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, sulfonyl pentafluoride, nitro, cyano, isocyano, amino, hydroxyl, methoxy, ethoxy, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, or thioisocyanate.

[0011] W1 Selected from , , , , , , or W 1 A hydrogen atom at any position on the aromatic ring may be replaced by one or more substituents U, wherein U is selected from straight-chain or branched alkyl groups, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, sulfonyl pentafluoride, nitro, cyano, isocyano, amino, hydroxyl, methoxy, ethoxy, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, or thioisocyanate, having 1 to 20 carbon atoms.

[0012] W 2 As shown in the following formula (W-1),

[0013] J 1 -T 1 -*(W-1)

[0014] In equation (W-1), T 1 Selected from straight-chain or branched alkylene groups 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-.

[0015] J 1 The group is selected from hydrogen atoms or polymerizable groups, wherein the polymerizable group is selected from the group shown in formula (J-1) or formula (J-2).

[0016]

[0017] M 1 M 2 M 3 and M 4Each is 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-,

[0018] B 1 and B 2 Each group is independently selected from the groups shown in formulas (B-1) to (B-5).

[0019]

[0020] C 1 and C 2 Each is independently selected from single bonds, -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-,

[0021] SP 1 and SP 2Each is independently selected from straight-chain or branched alkylene groups 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-.

[0022] L 1 and L 2 Each is independently selected from hydrogen atoms or polymeric groups, wherein the polymeric groups are selected from the groups shown in formula (J-1) or formula (J-2) above.

[0023] Optionally, Ar 2 The group is selected from the group represented by formula (Ar-1) or formula (Ar-2).

[0024] Optionally, J 1 The group is selected from the group shown in formula (J-1) or formula (J-2).

[0025] Optionally, L 1 and L 2 Each group is independently selected from the groups shown in formula (J-1) or formula (J-2).

[0026] Optionally, the liquid crystal compound is selected from the following structures:

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] .

[0049] According to a second aspect of this application, a liquid crystal composition is provided, comprising the liquid crystal compound described in the first aspect of this application.

[0050] Optionally, the liquid crystal composition further comprises a polymerizable compound;

[0051] The polymerizable compound is selected from the following structures:

[0052]

[0053] .

[0054] Optionally, the liquid crystal composition comprises 50 to 100 parts by weight of the liquid crystal compound and 0.1 to 50 parts by weight of the polymeric compound.

[0055] According to a third aspect of this application, a phase retardation film is provided, the phase retardation film being polymerized from the liquid crystal composition described in the second aspect of this application.

[0056] Optionally, the phase difference R450 at a wavelength of 450 nm and the phase difference R550 at a wavelength of 550 nm satisfy the following condition: R450 / R550 < 1.0.

[0057] The technical solution adopted in this invention can achieve the following beneficial effects:

[0058] This application provides a polymeric liquid crystal compound for forming a retardation film with excellent reverse wavelength dispersion and reliability. Furthermore, using a polymeric composition containing the polymeric liquid crystal compound provided in this application can suppress the generation of alignment defects during the retardation film manufacturing process. Therefore, by using the liquid crystal compound of this application, a retardation film with excellent reverse wavelength dispersion, excellent reliability, and fewer alignment defects can be prepared. Detailed Implementation

[0059] To make the objectives, technical solutions, and advantages of this invention clearer, the technical solutions of this invention will be clearly and completely described below in conjunction with specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this invention.

[0060] The inventors of this application, through research on the prior art, have discovered that liquid crystal compounds in the prior art typically have the following problems: 1. The disclosed compound structures usually have only one chromophore side chain, resulting in fewer chromophores and a higher R450 / R550 value, i.e., insufficient reverse wavelength dispersion; 2. These compound structures have fewer polymerizable groups and lower crosslinking completion, which is detrimental to the reliability of the system, such as changes in the optical properties of the optical film after high temperature; 3. Compositions containing these compounds are prone to alignment defects during film formation.

[0061] To address the aforementioned problems in the prior art, the inventors of this application conducted in-depth research and discovered that when a polymerizable liquid crystal compound has multiple chromophore side chains spaced at a certain distance, and each side chain contains a polymerizable group (e.g., acrylate), the compound exhibits excellent reverse wavelength dispersibility and reliability after film formation. Alignment defects are less likely to occur during the fabrication of retardation films using the above polymerizable liquid crystal compound.

[0062] In one embodiment, this application provides a polymerizable liquid crystal compound.

[0063] [Polymerizable liquid crystal compounds]

[0064] The polymeric liquid crystal compound of the present invention has the structure shown in formula (1).

[0065] L 1 -SP 1 -C 1 -Ar 1 -M 1 -B 1 -M 2 -Ar 2 -M 3 -B2 -M 4 -Ar 3 -C 2 -SP 2 -L 2 (1)

[0066] In equation (1), Ar 2 Ar is selected from aromatic rings represented by formulas (Ar-1) to (Ar-3) below. 1 and Ar 3 Each is independently selected from the aromatic rings represented by formula (Ar-1) or formula (Ar-2) below, and * indicates the bonding position.

[0067]

[0068] From the perspective of improving the inverse wavelength dispersion and reliability of the phase retardation film, Ar is preferred. 2 Selected from formula (Ar-1) or formula (Ar-2).

[0069] In the formulas (Ar-1) to (Ar-3), Q is selected from straight-chain or branched alkyl groups having 1 to 20 hydrogen atoms or carbon atoms.

[0070] V 1 V 2 V 3 and V 4 Each is independently selected from hydrogen atoms, straight-chain or branched alkyl groups having 1 to 10 carbon atoms, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, sulfonyl pentafluoride, nitro, cyano, isocyano, amino, hydroxyl, methoxy, ethoxy, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl or thioisocyano.

[0071] W 1 Selected from , , , , , , or W 1Hydrogen atoms at any position on the aromatic ring can be replaced by one or more substituents U, where U is selected from straight-chain or branched alkyl groups, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, sulfonyl pentafluoride, nitro, cyano, isocyano, amino, hydroxyl, methoxy, ethoxy, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, or thioisocyano. From the perspective of ease of obtaining raw materials and ease of synthesis, W is preferred. 1 Selected from or .

[0072] W 2 It can be represented by the following formula (W-1):

[0073] J 1 -T 1 -*(W-1)

[0074] In equation (W-1), T 1 Selected from straight-chain or branched alkylene groups 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 inverse wavelength dispersion and reliability of the phase retardation film, T is preferred. 1 Selected from -CH2CH2OCH2CH2OCH2CH2-.

[0075] J 1 Selected from hydrogen atoms or polymerizable groups, wherein the polymerizable groups are selected from the groups shown in formula (J-1) or formula (J-2) below:

[0076] .

[0077] From the perspective of improving the reliability of the phase retardation film, as a preferred implementation method, J 1 The group is selected from the group shown in formula (J-1) or formula (J-2).

[0078] M 1 M 2 M 3 and M 4Each is 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 perspective of liquid crystal properties and ease of synthesis, M is preferred. 1 M 2 M 3 and M 4 Each is independently selected from -OCH2-, -CH2O-, -COO-, -OCO-, or -O-CO-O-.

[0079] B 1 and B 2 Each group is independently selected from the groups shown in formulas (B-1) to (B-5) below.

[0080]

[0081] From the perspective of ease of obtaining raw materials and ease of synthesis, B is the preferred choice. 1 and B 2 Each independently selected or .

[0082] C 1 and C 2Each is independently selected from single bonds, -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-.

[0083] SP 1 and SP 2 Each is independently selected from straight-chain or branched alkylene groups 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-.

[0084] L 1 and L 2 Each is independently selected from hydrogen atoms or polymeric groups, and the polymeric groups are selected from the groups shown in formula (J-1) or formula (J-2) above.

[0085] From the perspective of improving the reliability of the phase retardation film, as a preferred implementation method, L 1 and L 2 Each group is independently selected from the groups shown in formula (J-1) or formula (J-2).

[0086] As the compound represented by formula (1), in particular, the compounds represented by formulas (R-1) to (R-22) are preferred.

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] .

[0109] There are no particular limitations on the method of manufacturing the compound represented by formula (1) of the present invention. It can be manufactured by appropriately combining known organic synthesis reactions (such as nucleophilic substitution reaction, esterification reaction, condensation reaction, Schiff base formation reaction, deprotection reaction, etc.) recorded in Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, etc., according to its structure.

[0110] According to another embodiment of this application, a liquid crystal composition comprising the above-described liquid crystal compound is also provided. This liquid crystal composition is also referred to as a "polymeric composition" in this invention, and the "polymeric composition" will be described in detail below.

[0111] [Polymerizable Composition]

[0112] The polymerizable composition of the present invention is a polymerizable composition containing the above-mentioned polymerizable liquid crystal compound. In addition to the polymerizable liquid crystal compound of the present invention, it may also contain other polymerizable compounds, photopolymerization initiators, stabilizers, other additives and solvents, etc., as described below.

[0113] [Other polymeric compounds]

[0114] In addition to the polymerizable liquid crystal compounds of the present invention described above, the polymerizable compositions of the present invention may also contain other polymerizable compounds that do not exhibit reverse wavelength dispersion, thereby adjusting wavelength dispersion, increasing crosslinking density, adjusting refractive index, inducing chiral phases, and reducing costs. Specifically, polymerizable compounds represented by the following formulas (N-1) to (N-12) are preferred:

[0115]

[0116] .

[0117] 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 polymeric compound. For example, in the liquid crystal composition of the present invention, the liquid crystal compound is present in weight parts of 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100 parts or any value between these numbers; and the polymeric compound is present in weight parts of 0.1, 0.5, 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50 parts or any value between these numbers.

[0118] [Photopolymerization initiator]

[0119] To form a crosslinked network through photoinitiated polymerization, a photoinitiator is generally required in the polymerizable composition. Examples of suitable photoinitiators for this invention include benzophenones, acetophenones, and benzoyl ketals. Furthermore, some brand-name initiators such as BASF OXE-01, OXE-02, OXE-03, OXE-04, and OXE-05 can also be added as photoinitiators. One photoinitiator can be used, or two or more photoinitiators can be used simultaneously. Relative to the polymerizable composition provided in this application, the photoinitiator accounts for 0.1% to 10% by mass, preferably 0.2% to 8% by mass, and more preferably 1% to 7% by mass, of the total mass of the polymerizable composition.

[0120] [Stabilizer]

[0121] To improve its storage stability, a stabilizer is generally required in the polymeric composition. Suitable stabilizers for this 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 relative to the total mass of the polymeric composition 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. One stabilizer can be used, or two or more stabilizers can be used simultaneously. 2,6-Di-tert-butyl-p-cresol (BHT) is preferably used as a stabilizer.

[0122] [Other adjuvants]

[0123] In actual coating production processes, other additives can be added as needed to ensure solution leveling, photocrosslinking efficiency, etc. For example, additives suitable for the compositions of the present invention may include one or more combinations of leveling and defoaming agents and chain transfer agents. The leveling and defoaming agents may be at least one of the following: BYK-300, BYK-306, BYK-358, BYK-354, BYK-515, BYK-3560, BYK-3566 (purchased from BYK Corporation); MEGAFACE F-554, F-556 (purchased from DIC Corporation); and Zonyl FS-520, Zonyl 8857A (purchased from DuPont Corporation). The amount of additive used is preferably 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.

[0124] [solvent]

[0125] In actual coating production processes, solvents are required to facilitate the coating process. Solvents suitable for the compositions of this invention mainly include benzenes, ketones, ethers, esters, halogenated hydrocarbons, and highly polar solvents. Benzene solvents mainly include: toluene, ethylbenzene, xylene, chlorobenzene, and anisole; ketone solvents mainly include: acetone, methyl ethyl ketone, 3-pentanone, cyclopentanone, cyclohexanone, and isophorone; ether solvents mainly include: 1,4-dioxane and tetrahydrofuran; ester solvents mainly include: ethyl acetate, butyl acetate, and propylene glycol methyl ether acetate; halogenated hydrocarbon solvents mainly include: dichloromethane, chloroform, and 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, and acetonitrile. You can use one solvent alone, or you can use two or more solvents at the same time.

[0126] [Phase difference film]

[0127] The phase retardation film of the present invention is formed by polymerization of the polymerizable composition described in the present invention. The phase difference R450 at a wavelength of 450 nm and the phase difference R550 at a wavelength of 550 nm satisfy the following condition: R450 / R550 < 1.0.

[0128] Example

[0129] The present invention will be further described below with reference to specific embodiments, but the present invention is not limited to the following embodiments.

[0130] Example 1

[0131] The preparation of the compound represented by formula (R-2)

[0132] Methyl trans-4-[(methanesulfonyloxy)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 water. N,N -Dimethylformamide was reacted at 100 °C for 24 hours. The reaction solution was poured into 200 mL of water and extracted three times with ethyl acetate. The concentrated organic phases were combined and subjected to column chromatography and recrystallization to give 4.8 g of white solid compound R-2a, with a yield of 58%.

[0133] Compound R-2a (4.8 g, 11.5 mmol) was dissolved in 80 mL of methanol. 23 mL of 2M sodium hydroxide aqueous solution was added dropwise at room temperature, and the reaction was carried out 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 under an ice-water bath for neutralization. The mixture was filtered, and the filter cake was dried to give 4 g of a white solid, compound R-2b, in 89% yield.

[0134] 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 added slowly dropwise under an 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. The crystals were filtered, and the filter cake was dried to give 6.1 g of a white solid compound R-2c, with a yield of 94%.

[0135] 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 water. N,N Dimethylformamide was slowly added to 6-chloro-1-hexanol (7.8 g, 57.2 mmol), and the reaction was carried out at 60 °C for 3 hours. The reaction solution was poured into 200 mL of water, extracted three times with ethyl acetate, and the concentrated organic phases were combined. The resulting mixture was subjected to column chromatography to give 6 g of a brown oily compound R-2d, with a yield of 78%.

[0136] 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 mixture was concentrated under reduced pressure, and column chromatography was performed to give 9.6 g of brown colloidal compound R-2f, in 91% yield.

[0137] Compound R-2f (9.6 g, 6.9 mmol) and N,N 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, and the reaction was carried out at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography and recrystallization to give 9.3 g of white solid compound R-2, in 69% yield. 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).

[0138] Example 2

[0139] Preparation of the compound represented by formula (R-4)

[0140]

[0141] 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 added dropwise slowly under an 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 subjected to column chromatography and recrystallization to give 1.8 g of white solid compound R-4b, yield 75%.

[0142] 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 mixture was concentrated under reduced pressure and subjected to column chromatography and recrystallization to give 1.8 g of white solid compound R-4c, in 63% yield.

[0143] Compound R-4c (1.8 g, 1.2 mmol) and N,N 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, and the reaction was carried out at room temperature for 1 hour. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography and recrystallization to give 1.5 g of white solid compound R-4, in 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).

[0144] Example 3

[0145] Preparation of the compound represented by formula (R-7)

[0146]

[0147] 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. The solution was slowly added dropwise under an 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 then subjected to column chromatography and recrystallization to give 1.8 g of white solid compound R-7b, in 98% yield.

[0148] Compounds 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 mixture was concentrated under reduced pressure and subjected to column chromatography and recrystallization to give 2.5 g of white solid compound R-7c, in 93% yield.

[0149] Compound R-7c (2.5 g, 1.6 mmol) and N,N Diisopropylethylamine (0.6 g, 4.7 mmol) was dissolved in 40 mL of dichloromethane, and acryloyl chloride (0.4 g, 4.7 mmol) was added dropwise under an ice-water bath. The reaction was carried out at room temperature for 1 hour. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography and recrystallization to give 2 g of white solid compound R-7, yield 76%. 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).

[0150] Example 4

[0151] Preparation of the compound represented by formula (R-10)

[0152] 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 added dropwise slowly in an ice-water bath. N,N’ -Diisopropylcarbodiimide (3.3 g, 26.4 mmol), 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 give 7.9 g of a white solid compound R-10b, 100% yield.

[0153] 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 water. N,N Dimethylformamide was slowly added to 6-bromo-hexanol (6.3 g, 34.6 mmol), 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 concentrated organic phases were combined, and the resulting mixture was subjected to column chromatography and recrystallization to give 4.8 g of brown solid compound R-10c, with a yield of 98%.

[0154] 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 mixture was concentrated under reduced pressure, and column chromatography was performed to give 6.3 g of brown colloidal compound R-10d, in 93% yield.

[0155] Compound R-10d (5.8 g, 3.4 mmol) and N,N 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, and the reaction was carried out at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography to give 3.1 g of a pale yellow oil, compound R-10, in 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).

[0156] Example 5

[0157] Preparation of the compound represented by formula (R-16)

[0158]

[0159] 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 water. N,N Dimethylformamide was slowly added to 2-(2-bromoethoxy)ethanol (5.9 g, 34.6 mmol), and the reaction was carried out at 60 °C for 3 hours. The reaction solution was poured into 200 mL of water, extracted three times with ethyl acetate, and the concentrated organic phases were combined. The resulting mixture was subjected to column chromatography to give 3.1 g of a brown oily compound R-16a, with a yield of 64%.

[0160] 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 mixture was concentrated under reduced pressure, and column chromatography was performed to give 3.5 g of brown colloidal compound R-16b, in 56% yield.

[0161] Compound R-16b (3.5 g, 2.1 mmol) and N,N Diisopropylethylamine (2.2 g, 16.7 mmol) was dissolved in 50 mL of dichloromethane. Acryloyl chloride (1.5 g, 16.7 mmol) was added dropwise under an ice-water bath, and the reaction was carried out at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography to give 2.8 g of a white colloidal compound R-16, in 69% yield. 1 H 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).

[0162] Example 6

[0163] Preparation of the compound represented by formula (R-18)

[0164]

[0165] 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 mixture was concentrated under reduced pressure, and column chromatography was performed to give 3.1 g of white solid compound R-18b, in 79% yield.

[0166] Compound 18b (3 g, 1.8 mmol) and N,N 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, and the reaction was carried out at room temperature for 4 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography and recrystallization to give 2.8 g of white solid compound R-18, in 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).

[0167] Example 7

[0168] Preparation of the compound represented by formula (R-20)

[0169]

[0170] 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 mixture was concentrated under reduced pressure and subjected to column chromatography to give 3 g of white solid compound R-20b, in 78% yield.

[0171] Compound 20b (3 g, 1.8 mmol) and N,N 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, and the reaction was carried out at room temperature for 4 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was subjected to column chromatography and recrystallization to give 2.4 g of white solid compound R-20, in 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).

[0172] Comparative Example 1

[0173] Compound represented by formula (X-1)

[0174]

[0175] Comparative Example 2

[0176] Compound represented by formula (X-2)

[0177]

[0178] [Preparation of phase retardation films]

[0179] Photoaligning agent HSPA-252B (manufactured by Osaka Organics) was uniformly coated onto a 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. On the glass substrate with the alignment layer, the polymerizable composition solution described in Table 1 was uniformly coated onto each substrate using a spin coater (600 rpm, 30 s), and dried at 100 °C to evaporate the solvent. Subsequently, the substrate was cooled to room temperature, and the film surface containing the composition was irradiated with a mercury lamp under a nitrogen atmosphere with a total energy of 1500 mJ / cm². 2 That is, a phase difference film is obtained, as shown in Examples 8-14 and Comparative Examples 3-4 in Table 2.

[0180] Table 1

[0181]

[0182] [Wavelength Dispersion]

[0183] For the fabricated retardation film, the phase difference at various wavelengths was measured using an Axoscan polarimeter. The phase difference R450 at 450 nm and R550 at 550 nm were recorded. The ratio R450 / R550 was calculated and evaluated according to the following criteria. The results are shown in Table 2 below, where a smaller R450 / R550 ratio indicates better inverse wavelength dispersion.

[0184] A: R450 / R550 is less than or equal to 0.8

[0185] B: R450 / R550 is greater than 0.8 and less than or equal to 0.85

[0186] C: R450 / R550 is greater than 0.85 and less than or equal to 0.9

[0187] D: R450 / R550 is greater than 0.9

[0188] [Alignment Defect]

[0189] The number of alignment defects on the fabricated phase retardation film was visually confirmed using an optical microscope, and evaluated according to the following evaluation criteria. The results are shown in Table 2 below.

[0190] A: No defects

[0191] B: 1 to 10

[0192] C: 11-100

[0193] D: The entire surface has alignment defects (>100).

[0194] [Reliability]

[0195] The fabricated retardation film was transferred onto a linear polarizer using pressure-sensitive adhesive, and then bonded with the slow axis of the retardation film at 45° to the absorption axis of the linear polarizer. The bonded composite film was placed in an 85°C high-temperature test chamber for 72 hours, then removed and cooled to room temperature. The ellipticity curve from 400 to 700 nm was measured using an Axoscan polarimeter to obtain the wavelength of maximum ellipticity. The deviation of the maximum ellipticity wavelength of the composite film before and after the high-temperature test was compared. The results are shown in Table 2 below, where a smaller deviation of the maximum wavelength indicates better reliability of the retardation film.

[0196] A: The deviation of the maximum wavelength is less than or equal to 5 nm.

[0197] B: The deviation of the maximum wavelength is greater than 5 nm and less than or equal to 10 nm.

[0198] C: The deviation of the maximum wavelength is greater than 10 nm and less than or equal to 15 nm.

[0199] D: The deviation of the maximum wavelength is greater than 15 nm.

[0200] Table 2

[0201]

[0202] The results shown in Table 2 reveal that the polymeric liquid crystal compound X-2 used in Comparative Example 4 has only one chromophore side chain, resulting in the worst reverse wavelength dispersibility after film formation (wavelength dispersibility rating "D"). The polymeric liquid crystal compound X-1 used in Comparative Example 3 has no polymeric side chain, which is detrimental to the reliability of the system after film formation (reliability rating "D").

[0203] In contrast, the polymeric liquid crystal compounds used in Examples 8-10 of this application each have two side chains, and each side chain contains both a chromophore and a polymeric group (e.g., acrylate); the polymeric liquid crystal compounds used in Examples 11-14 of this application each have three side chains, and each side chain contains both a chromophore and a polymeric group. This results in the phase retardation film formed by the polymeric liquid crystal compounds provided in this application exhibiting excellent reverse wavelength dispersion and reliability, while the alignment defect problem is significantly improved (Examples 8-14). Specifically, comparing Examples 11-14 with Examples 8-10 of this application shows that the more chromophores and polymeric groups on the side chains of the polymeric liquid crystal compounds, the better the reverse wavelength dispersion and reliability (compared to Examples 8-10, the reverse wavelength dispersion and reliability ratings of Examples 11-14 are all "A").

[0204] In summary, the present invention provides a polymeric liquid crystal compound for forming a retardation film with excellent reverse wavelength dispersion and reliability. The retardation film prepared from a polymeric composition containing the polymeric liquid crystal compound of the present invention is less prone to alignment defects during manufacturing, and exhibits excellent reverse wavelength dispersion and reliability.

[0205] The embodiments of this application have been described above, but this application is not limited to the specific embodiments described above. The specific embodiments described above are merely illustrative and not restrictive. Those skilled in the art can make many other forms under the guidance of this application without departing from the spirit and scope of the claims, and all of these forms are within the protection scope of this application.

Claims

1. A liquid crystal compound, characterized by, 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 groups represented by the following formulae (Ar-1) to (Ar-3), Ar 1 and Ar 3 are each independently selected from groups represented by the following formula (Ar-1) or formula (Ar-2), * indicates a bonding position, In formulas (Ar-1) to (Ar-3), Q is selected from hydrogen atoms. 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, W 1 selected from , W 2 As shown in the following formula (W-1), J 1 -T 1 -*(W-1) In formula (W-1), T 1 is selected from a linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or a plurality of -CH2- that are not adjacent to each other can be replaced independently with -0-, -CO-, -COO-, -OCO-, J 1 a polymerizable group selected from a 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-, B 1 and B 2 each independently is selected from a group represented by the following formula (B-4), C 1 and C 2 are each independently selected from a single bond or -O-, SP 1 and SP 2 each independently is selected from a linear or branched alkylene group having 1 to 20 carbon atoms, wherein any one -CH2- or a plurality of -CH2- that are not adjacent to each other, can each independently be replaced with -O-, -COO-, or -OCO-, L 1 and L 2 each independently is selected from a polymerizable group selected from the group consisting of the groups represented by formula (J-1) or formula (J-2) described above.

2. The liquid crystal compound according to claim 1, characterized by Ar 2 is selected from the group consisting of the radicals of the formula (Ar-1) or of the formula (Ar-2).

3. The liquid crystal compound according to claim 1, characterized by The liquid crystal compound is selected from the following structures: 。 4. A liquid crystal composition, characterized by comprising The liquid crystal compound comprising any one of claims 1 to 3.

5. The liquid crystal composition according to claim 4, characterized by The liquid crystal composition further comprises a polymerizable compound; The polymerizable compound is selected from the following structures: 。 6. The liquid crystal composition according to claim 5, characterized by The liquid crystal composition comprises, by weight, 50 to 100 parts of the liquid crystal compound and 0.1 to 50 parts of the polymeric compound.

7. A phase difference film characterized by, The phase retardation film is polymerized from the liquid crystal composition according to any one of claims 4 to 6.

8. The phase retardation film according to claim 7, characterized in that, The phase difference R450 of the phase retardation film at a wavelength of 450 nm and the phase difference R550 at a wavelength of 550 nm satisfy the following: R450 / R550 < 1.0.

Images