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

Abstract

The invention discloses a liquid crystal compound, a liquid crystal composition and a phase difference film, relates to the technical field of liquid crystal display, and aims to solve the problems of poor alignment order degree, low n value and low crosslinking completion degree in an existing liquid crystal system. The structural general formula (I) of the liquid crystal compound is set, and the liquid crystal compound is applied to the phase difference film. According to the liquid crystal compound, a long liquid crystal main chain is adopted, so that liquid crystal molecules are arranged more orderly, dense chromophoric group arrangement is achieved, Van der Waals force and hydrogen-bond interaction among the liquid crystal molecules are improved, the alignment order degree and the n value are improved, and the purposes of improving dispersion, lowering the manufacturing cost, lowering the film thickness requirement and improving the crosslinking completion degree are achieved.

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 film is a key component in modern display technology. It can affect the display quality, such as display brightness, clarity, and large viewing angle color deviation. Among them, the reverse wavelength dispersion phase difference film is widely used in the polarizer of liquid crystal display (LCD) and organic light emitting diode display (OLED) for anti-reflection and viewing angle compensation due to its unique optical properties. Reverse wavelength dispersion usually refers to the proportional relationship between the phase difference and the wavelength at the normal viewing angle, usually expressed by the phase difference R450 at a wavelength of 450nm and the phase difference R550 at a wavelength of 550nm satisfying the following conditions: R450 / R550≤1.0.

[0003] The phase difference film that achieves reverse wavelength dispersion currently mainly uses liquid crystal polymer materials, which use the birefringence of the material to cause phase difference. Mainstream, these liquid crystal polymers usually use prepolymer coating liquid as a precursor, and the precursor contains liquid crystal monomers with polymerizable groups, initiators, solvents, etc. In order for the liquid crystal to obtain a certain orientation, there should also be a functional alignment layer on the substrate it carries. After the precursor solution is coated on the substrate containing the alignment layer, it goes through a heating and drying step, and after the solvent evaporates, the liquid crystal compound forms a liquid crystal phase with a specific orientation (ie, "alignment") under certain temperature conditions. Subsequently, the polymerization reaction is initiated by ultraviolet light to fix the alignment of the liquid crystal, thereby obtaining an anisotropic polymer film with a regular orientation, which then has the optical properties of phase difference.

[0004] The existing reverse wavelength dispersion monomer molecular structure is mainly composed of a main chain and a chromophore side chain (reference patents: US20180346614, CN113150792A, WO2017043438, US8323527, US8687259B2, CN1950350). These monomers can exhibit fairly good reverse wavelength dispersion, with the number of six-membered ring monomers in the main chain being 5 or less, and the chromophore of the side chain being 1 unit / molecule. However, under this molecular structure, the chromophores are not dense, and the presence of chromophores easily disrupts the order of the liquid crystal arrangement, resulting in poor alignment order in these liquid crystal systems, thereby reducing the △n value. The consequences of low △n are: First, the problem of high dispersion R450 / R550 values. In order to reduce dispersion, the content of reverse wavelength dispersion monomers in the formula increases, increasing the manufacturing cost. Second, the film thickness required to achieve the target R550 increases, increasing the amount of material required per unit area, and thus increasing the cost. In addition, since the molecular weight of these reverse wavelength dispersion monomers is too small and the polymerizable groups are too dense, the shrinkage rate of the cross-linking system is too large during photocuring, which ultimately leads to a low degree of 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. Summary of the invention

[0005] The invention discloses a liquid crystal compound, a liquid crystal composition and a phase difference film, so as to solve the problems of poor alignment order, low △n value and low cross-linking completion degree in the existing liquid crystal system.

[0006] In order to achieve the above purpose, the embodiments of this specification adopt the following technical solutions: In a first aspect, the embodiments of the present application provide a liquid crystal compound, the structure of which satisfies the general formula (I): (I); In the general formula (I), 3≤x≤10, 2≤y≤5, wherein x is a positive integer, and y is a positive integer; In the general formula (I), A1 represents , the two bonding positions on A1 can be arbitrarily reversed, where 0≤m1+m2+m3≤15, m1 is a positive integer, m2 is a positive integer, and m3 is a positive integer; -CH2-, -O-, and -COO- in A1 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A1 can be arbitrarily selected to be positive or negative; In the general formula (I), A2 represents , the two bonding positions on A2 can be arbitrarily reversed, where 0≤n1+n2+n3≤15, n1 is a positive integer, n2 is a positive integer, and n3 is a positive integer; -CH2-, -O-, and -COO- in A2 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A2 can be arbitrarily selected to be positive or negative; In the general formula (I), L1~L x Each independently selected from a single bond, , , , , , , , The two bonding positions on the can be reversed at will; In the general formula (I), G1~G x Each is independently selected from 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,3-dioxane-2,5-diyl; G1~G x The two bonding positions on the G1~G x The H on the molecule is unsubstituted or substituted by one or more substituents Sp1, and the substituted Sp1 groups are the same or different; Sp1 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp1 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp1 can be replaced by a fluorine atom; In the general formula (I), R1 and R2 are each independently selected from a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, , , , or Group; In the general formula (I), Ar1~Ary is a 5- to 10-membered aromatic ring or aromatic heterocyclic ring; Ar1~Ar y The H on the SG1~SG y Substituted or substituted by one or more substituents Sp2; Sp2 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp2 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp2 can be replaced by a fluorine atom; In the general formula (I), M1~M y Each independently selected from a single bond, , , , , M1~M y The two bonding positions on the can be reversed at will; In the general formula (I), SG1~SG y The structure is the general formula (II): (II); In the general formula (II), J1~J yeach independently selected from a single bond, -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -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=C H-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-, -C≡C-, , ,or , J1~J y The two bonding positions on the top have no left or right direction regulations and can be selected arbitrarily; Among them, Q is used Indicates that T1 is selected from , The two bonding positions on the ester bond can be arbitrarily reversed; 0≤p1+p2+p3≤16, p1 is a positive integer, p2 is a positive integer, and p3 is a positive integer; -CH2-, -O-, and -COO- in T1 can be arranged in any order except for forming -OO-, and the direction of the ester bond represented by -COO- in T1 can be arbitrarily selected to be positive or negative; R3 is selected from hydrogen atom, methyl, ethyl, methoxy, , , , , Group; In the general formula (II), E1~E y are each independently selected from a single bond, (1≤q≤5), , , , , , ; E1~E y The two bonding positions on the top have no left or right regulations and can be selected arbitrarily; E1~E y is unsubstituted or substituted by one or more substituents Sp3; Sp3 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp3 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp3 can be replaced by a fluorine atom.

[0007] In the general formula (II), Z1~Z y is a 5- to 14-membered aromatic ring or aromatic heterocyclic ring; Z1~Z y The H on the molecule is unsubstituted or can be substituted by one or more substituents Sp4. Replace, and E1~E y Link; Sp4 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp4 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp4 can be replaced by a fluorine atom; In, T2 is selected , Where r is 0 to 10, R4 is selected from methyl, ethyl, methoxy, , , , , Group.

[0008] Optionally, M1~M y Each independently selected from , , ,or .

[0009] Optionally, in SG1~SG y In the general structural formula (II), J1~J y Selected from , when E is a single bond and Z is a benzothiazole group, p2+p3≠0 in Q.

[0010] Optionally, SG1~SG y The structural formula is: .

[0011] In a second aspect, an embodiment of the present application provides a liquid crystal composition, including: the above-mentioned liquid crystal compound and a polymerizable liquid crystal compound.

[0012] Optionally, the liquid crystal composition comprises: 5 parts by weight or more of a liquid crystal compound, and 5 parts by weight or more of a polymerizable liquid crystal compound.

[0013] Optionally, the liquid crystal composition comprises: 50 to 90 parts by weight of a liquid crystal compound and 10 to 50 parts by weight of a polymerizable liquid crystal compound.

[0014] Optionally, the polymerizable liquid crystal compound is selected from the following structures:

[0015] In a third aspect, an embodiment of the present application provides a phase difference film, which is formed by polymerizing the above-mentioned liquid crystal composition.

[0016] 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 are R450 / R550≤1.0.

[0017] At least one of the above technical solutions adopted in the embodiments of the present application can achieve the following beneficial effects: (1) Improved dispersion: Compared with the monomers in the prior art in which the number of main chain six-membered ring monomers is 5 or less and the side chain chromophore group is 1 unit / molecule, the reverse wavelength dispersion monomer provided by the present invention can more effectively improve the order of liquid crystal, thereby reducing dispersion and improving the performance of the optical film.

[0018] (2) Reducing manufacturing costs: Since the reverse wavelength dispersion monomer of the present invention can increase the Δn value, the content of the reverse wavelength dispersion monomer can be reduced in the formula, thereby reducing the manufacturing cost. Compared with the practice in the prior art of increasing the content of the reverse wavelength dispersion monomer in order to reduce the dispersion, the present invention provides a more economical and practical solution.

[0019] (3) Reduced film thickness requirements: Since the reverse wavelength dispersion monomer of the present invention can increase the Δn value, the phase difference required for the target R550 can be achieved at a lower film thickness. This not only reduces the amount of material required per unit area, thereby reducing costs, but also increases the thinness of the optical film, meeting the requirements of modern display technology for thinness.

[0020] (4) Improved cross-linking completion: Since the reverse wavelength dispersion monomer of the present invention has a large molecular weight and relatively dispersed polymerizable groups, the shrinkage rate of the cross-linking system is small during light curing, and the cross-linking reaction proceeds more smoothly, ultimately resulting in a higher degree of cross-linking completion. This improves the reliability of the optical film and ensures that the optical film can maintain good optical properties after high temperature or other environmental changes. DETAILED DESCRIPTION

[0021] In order to make the purpose, technical scheme and advantages of the present application clearer, the technical scheme of the present application will be clearly and completely described below in conjunction with the specific embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present application.

[0022] According to one embodiment of the present application, a liquid crystal compound is provided, the structure of which satisfies the general formula (I): (I); In the general formula (I), 3≤x≤10, 2≤y≤5, wherein x is a positive integer, y is a positive integer, and the x and y in brackets represent a group combination, that is, , can be arranged in any order. Preferably, x is 5, 6 or 7, and y is 2 or 3.

[0023] In the general formula (I), A1 represents , the two bonding positions on A1 can be arbitrarily reversed, where 0≤m1+m2+m3≤15, m1 is a positive integer, m2 is a positive integer, and m3 is a positive integer; -CH2-, -O-, and -COO- in A1 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A1 can be arbitrarily selected to be positive or negative; In the general formula (I), A2 represents , the two bonding positions on A2 can be arbitrarily reversed, where 0≤n1+n2+n3≤15, n1 is a positive integer, n2 is a positive integer, and n3 is a positive integer; -CH2-, -O-, and -COO- in A2 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A2 can be arbitrarily selected to be positive or negative; Preferably, A1 and A2 are , here* can connect G1~G x 、L1~L x 、Ar1~Ar x or M1~M x Group.

[0024] In the general formula (I), L1~L x are each independently selected from a single bond, , , , , , , , The two bonding positions on the PCB can be reversed at will.

[0025] In the general formula (I), G1~G x Each is independently selected from 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,3-dioxane-2,5-diyl; G1~G x The two bonding positions on the G1~G x The H on the molecule is unsubstituted or substituted by one or more substituents Sp1, and the substituted Sp1 groups may be the same or different, and the "one or more" herein includes "one".

[0026] Sp1 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp1 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp1 can be replaced by a fluorine atom.

[0027] From the perspective of structural universality and availability, G1~G x Preferred use: .

[0028] In the general formula (I), R1 and R2 are each independently selected from a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, , , , or Group.

[0029] In the general formula (I), Ar1~Ar y is a 5- to 10-membered aromatic ring or aromatic heterocyclic ring; Ar1~Ar y The H on the SG1~SG y Substituted or substituted by one or more substituents Sp2, where one or more includes one; Sp2 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp2 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp2 can be replaced by a fluorine atom.

[0030] Preferably, Ar1~Ar y Preferred use , .

[0031] In the general formula (I), M1~M y Each independently selected from a single bond, , , , , M1~M y The two bonding positions on the PCB can be reversed at will.

[0032] Preferably, M1~M y Each independently selected from , , or

[0033] In the general formula (I), SG1~SG y The structure is the general formula (II): (II); In the general formula (II), J1~J y each independently selected from a single bond, -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -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=C H-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-, -C≡C-, , ,or , J1~J y The two bonding positions on the top have no left or right direction regulations and can be selected arbitrarily; Among them, Q is used Indicates that T1 is selected from , The two bonding positions on the ester bond can be arbitrarily reversed; 0≤p1+p2+p3≤16, p1 is a positive integer, p2 is a positive integer, and p3 is a positive integer; -CH2-, -O-, and -COO- in T1 can be arranged in any order except for forming -OO-, and the direction of the ester bond represented by -COO- in T1 can be arbitrarily selected to be positive or negative; R3 is selected from hydrogen atom, methyl, ethyl, methoxy, , , , , Group.

[0034] Preferably, in SG1~SG y In the general structural formula (II), J1~J y Selected from , when E is a single bond and Z is a benzothiazole group, p2+p3≠0 in Q.

[0035] In the general formula (II), E1~E y Each independently selected from a single bond, (1≤q≤5), , , , , , ; E1~E y The two bonding positions on the top have no left or right regulations and can be selected arbitrarily; E1~E y is unsubstituted or substituted with one or more substituents Sp3, where one or more includes one; Sp3 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp3 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp3 can be replaced by a fluorine atom.

[0036] In the general formula (II), Z1~Z y is a 5- to 14-membered aromatic ring or aromatic heterocyclic ring; Z1~Z yThe H on the molecule is unsubstituted or can be substituted by one or more substituents Sp4. Replace, and E1~E y Link.

[0037] Sp4 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp4 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp4 can be replaced by a fluorine atom; In, T2 is selected , Where r is 0 to 10, R4 is selected from methyl, ethyl, methoxy, , , , , Group.

[0038] Considering the simplicity, convenience and availability of molecular structure, the following are some SG1~SG y Preferred structures of the group: .

[0039] The following are preferably liquid crystal compounds conforming to the general formula (I):

[0040] The preparation method of the liquid crystal compound of the general formula (I) is not particularly limited and can be synthesized by a known method, for example, by the method described in CN107108458B, CN101470212B, CN113150792A, CN104245885B, CN1950350A, JP2005208416A, March's Advanced Organic Chemistry (Wiley), and Greene's Protective Groups In Organic Synthesis 4th Edition (Wiley).

[0041] According to one embodiment of the present application, a liquid crystal composition is provided, including: a liquid crystal compound and a polymerizable liquid crystal compound.

[0042] The liquid crystal composition comprises: 5 parts by weight or more of a liquid crystal compound, and 5 parts by weight or more of a polymerizable liquid crystal compound. Preferably, the liquid crystal composition comprises: 50 to 90 parts by weight of a liquid crystal compound, and 10 to 50 parts by weight of a polymerizable liquid crystal compound.

[0043] In the liquid crystal composition, the liquid crystal compound can be used as a reverse wavelength dispersion monomer, and one or more of the general formula (I) can be added. The polymerizable liquid crystal compound exhibits positive wavelength dispersion, and when blended with a reverse wavelength dispersion monomer, it plays a role in adjusting wavelength dispersion, increasing crosslinking density, adjusting refractive index, inducing chiral phase, and reducing costs. The following are preferred polymerizable liquid crystal compounds:

[0044] In order to form a cross-linked network by photoinitiated polymerization, a photoinitiator is generally required to be added to the liquid crystal composition. The photoinitiator suitable for the present invention may include, but is not limited to, the compounds described in the following formulas I-1 to I-7, and some brand initiators such as BASF OXE-03, OXE-04, etc. can also be added.

[0045]

[0046] In the liquid crystal composition of the present invention, the weight portion of the photoinitiator is 0.2 to 10 parts, preferably 3 to 7 parts. For example, in the liquid crystal composition provided by the present invention, the weight portion of the photoinitiator can be 0.2 parts, 0.4 parts, 0.6 parts, 0.8 parts, 1 parts, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts, 9 parts, 10 parts or any value between these numbers.

[0047] In the actual coating production process, other additives can be added as needed to ensure solution stability, leveling, photocrosslinking efficiency, etc. For example, the additives suitable for the liquid crystal composition of the present invention may include a combination of one or more of a leveling defoaming aid, an inhibitor, and a chain transfer agent. Among them, the leveling defoaming aid can be BYK-300, BYK-306, BYK-358, BYK-354, BYK-515, BYK-3560, BYK-3566 purchased from BYK; MEGAFACE F-554, F-556 purchased from DIC; and Zonyl FS-520, Zonyl 8857A purchased from DuPont. The inhibitor suitable for the present invention may include at least one of benzoquinone, hydroquinone, and 2,6-di-tert-butyl-4-methylphenol (BHT); the chain transfer agent suitable for the present invention may include at least one of dodecanethiol and triethylamine.

[0048] In the liquid crystal composition of the present invention, the weight portion of the auxiliary agent is 0.01 to 5 parts, preferably 0.1 to 1 parts. For example, in the liquid crystal composition of the present invention, the weight portion of the auxiliary agent suitable for addition is 0.01 parts, 0.02 parts, 0.04 parts, 0.06 parts, 0.08 parts, 0.1 parts, 0.2 parts, 0.3 parts, 0.4 parts, 0.5 parts, 0.6 parts, 0.7 parts, 0.8 parts, 0.9 parts, 1 parts, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts or any value between these numbers.

[0049] In the actual production process of optical films using liquid crystal compositions, solvents are needed to assist in coating processing. Solvents suitable for the liquid crystal composition of the present invention mainly include benzene, ketones, esters and high polarity solvents. Benzene solvents mainly include: toluene, xylene, chlorobenzene, ethylbenzene; ketone solvents mainly include: butanone, 3-pentanone, cyclopentanone, cyclohexanone, N-methylpyrrolidone, isophorone; ester solvents mainly include: ethyl acetate, butyl acetate, propylene glycol methyl ether acetate; high polarity solvent solvents mainly include: n-butanol, isopropanol, propylene glycol methyl ether, N,N-dimethylformamide, ethanolamine, acetonitrile. In one embodiment, one solvent can be used. In another embodiment, the above solvents can be used in combination. Among them, in terms of weight parts (and calculated by non-volatile content), 100 to 1200 parts by weight of solvent can be added to the above liquid crystal composition, preferably 250 to 350 parts by weight of solvent. For example, in the above-mentioned liquid crystal composition of the present invention, 100, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 295, 300, 305, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 325, 330, 335, 340, 350, 360, 370, 380, 390, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200 parts of at least one of the above-mentioned solvents can be added in parts by weight.

[0050] In another embodiment of the present application, an anisotropic body is also provided, wherein the anisotropic body is obtained from the above-mentioned liquid crystal composition of the present application through a polymerization reaction.

[0051] In another embodiment of the present application, an optical film is provided. The optical film includes a polymerized product generated by a polymerization reaction of the liquid crystal composition described in the present application or includes the anisotropic body described in the present application.

[0052] In another embodiment of the present application, a phase difference film is also provided, which includes a polymerization product generated by a polymerization reaction of the liquid crystal composition described in the present application or includes the above-mentioned anisotropic body of the present application, wherein the phase difference R450 of the phase difference film at a wavelength of 450nm and the phase difference R550 at a wavelength of 550nm satisfy the following condition: R450 / R550≤1.0.

[0053] The main technical means adopted in this technical solution are: 1. Using a longer liquid crystal main chain: By adopting a longer liquid crystal main chain (more than 5 six-membered rings), the order of the liquid crystal curing system can be enhanced, the △n value can be improved, the dispersion can be reduced, and the cross-linking completion degree can be improved. The longer liquid crystal main chain can provide more steric hindrance, making the arrangement of liquid crystal molecules more orderly, thereby improving the alignment order and △n value. 2. Dense chromophore arrangement: By adopting a dense chromophore arrangement (more than 2 units per molecule), the interaction between liquid crystal molecules can be enhanced, and the order of the liquid crystal curing system can be further improved. The dense chromophore arrangement can increase the van der Waals force and hydrogen bonding between liquid crystal molecules, thereby improving the alignment order and △n value.

[0054] Compared with the prior art, this technical solution mainly solves the following problems: 1. Improving the alignment order of reverse wavelength dispersion monomers, increasing the △n value, and reducing dispersion; 2. Reducing the usage of reverse wavelength dispersion monomers, reducing manufacturing costs, and reducing the preparation cost of optical films; 3. Increasing the reliability issues such as the high temperature resistance of optical films.

[0055] The technical solutions provided by each embodiment of the present application are described in detail below.

[0056] Example 1: Synthesis of R-5 Trans-4-[4-(6-acryloyloxyhexyloxy)phenoxycarbonyl]cyclohexanecarboxylic acid (50 g, 120 mmol), 2,5-dihydroxybenzaldehyde (18.2 g, 132 mmol), and 4-dimethylaminopyridine (1.5 g, 12 mmol) were dissolved in 300 mL of dichloromethane. N,N'-diisopropylcarbodiimide (16.6 g, 132 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 37 g of white solid compound 1a with a yield of 58%.

[0057] Hydrazinobenzothiazole (197 g, 120 mmol) and cesium carbonate (78 g, 240 mmol) were dissolved in a mixed solution of 800 mL tetrahydrofuran and 800 mL N,N-dimethylformamide and stirred for 1 hour in an ice-water bath. 2-Chloroethoxy-2-ethoxydiethanol (30 g, 180 mmol) was slowly added dropwise and reacted at 80°C for 12 hours. Ethyl acetate was added, and the organic phase was washed with water and saturated brine successively and concentrated. The resulting mixture was subjected to column chromatography to obtain 210 g of light brown solid compound 1b with a yield of 59%.

[0058] Trans-1,4-cyclohexanedicarboxylic acid (17.2 g, 100 mmol) was dissolved in 5 mL of thionyl chloride, and a catalytic amount of N,N-dimethylformamide was added, and the mixture was refluxed for 1 hour. The mixture was concentrated under reduced pressure, and the resulting mixture was recrystallized to obtain 11.8 g of colorless needle-shaped crystals of compound 1c, with a yield of 56%.

[0059] Compound 1a (25 g, 46.5 mmol), compound 1c (4.85 g, 23.2 mmol), and N,N-diisopropylethylamine (6 g, 46.5 mmol) were dissolved in 200 mL DCM and reacted at room temperature for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 16 g of white solid compound 1d with a yield of 57%.

[0060] Compound 1d (16 g, 13.2 mmol), compound 1b (8.6 g, 29 mmol), and chromatic camphorsulfonic acid (6.1 g, 26.4 mmol) were dissolved in 200 mL of chloroform and reacted at 70 °C for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 18.9 g of white solid compound 1e with a yield of 81%.

[0061] Compound 1e (18.9 g, 10.7 mmol) and N,N-diisopropylethylamine (5.5 g, 42.8 mmol) were dissolved in 200 mL of dichloromethane, and acryloyl chloride (3.9 g, 42.8 mmol) was added dropwise under an ice-water bath, and reacted at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 16 g of white solid compound R-5 with a yield of 80%. 1 H NMR (500 MHz, CDCl3) δ8.00 (s, 2H), 7.74 (s, 2H), 7.71-7.64 (m, 4H), 7.37-7.32 (m, 2H), 7.20-7.15(m, 2H), 7.14-7.08 (m, 4H), 6.99(d, J = 8.7 Hz, 4H), 6.88 (d, J = 8.9 Hz, 4H),6.43-6.33 (m, 4H), 6.17-6.04 (m, 4H), 5.84-5.73 (m, 4H), 4.48 (t, J = 5.3 Hz,4H), 4.22-4.14 (m, 8H), 3.95 (t, J = 6.4 Hz, 4H), 3.88 (t, J= 5.4 Hz, 4H), 3.65-3.56 (m, 12H), 2.78-2.72 (m, 2H), 2.69-2.59 (m, 4H), 2.43-2.28 (m, 12H), 1.84-1.76 (m, 8H), 1.75-1.65 (m, 12H), 1.55-1.43 (m, 8H).

[0062] The specific preparation process is as follows:

[0063] Example 2: Synthesis of R-1 2-Hydrazinobenzothiazole (7.26 g, 44 mmol) and cesium carbonate (28.7 g, 88 mmol) were dissolved in a mixed solution of 50 mL tetrahydrofuran and 50 mL N,N-dimethylformamide and stirred for 1 hour in an ice-water bath. Diethylene glycol-2-bromoethyl methyl ether (15 g, 66 mmol) was slowly added dropwise and reacted at 80 °C for 12 hours. Ethyl acetate was added, and the organic phase was washed with water and saturated brine successively and concentrated. The resulting mixture was subjected to column chromatography to obtain 8.2 g of light yellow oily compound 2a with a yield of 60%.

[0064] Compound 1d (5 g, 4.1 mmol), compound 2a (2.8 g, 9 mmol), and chromatic camphorsulfonic acid (1.9 g, 8.2 mmol) were dissolved in 100 mL of chloroform and reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 4.4 g of white solid compound R-1 with a yield of 60%. 1 H NMR (400 MHz, CDCl3) δ 8.01 (s, 2H), 7.75 (s,2H), 7.72-7.64 (m, 4H), 7.37-7.32 (m, 2H), 7.20-7.15 (m, 2H), 7.14-7.08 (s,4H), 6.99 (d, J = 7.8 Hz, 4H), 6.88 (d, J = 7.9 Hz, 4H), 6.41 (d, J = 17.3 Hz, 2H),6.13 (dd, J = 17.2, 10.5 Hz, 2H), 5.82 (d, J = 10.3 Hz, 2H), 4.51-4.46 (m, 4H), 4.18 (t, J = 6.5 Hz, 4H), 3.95 (t,J = 6.1 Hz, 4H), 3.89 (d, J = 4.6 Hz, 4H), 3.67-3.62 (m, 4H), 3.60-3.55 (m, 4H), 3.55-3.50 (m, 4H), 3.42-3.37 (m, 4H), 3.27(s, 6H), 2.79-2.72 (m, 2H), 2.70-2.58 (m, 4H), 2.44-2.29 (m, 12H), 1.84-1.68(m, 20H), 1.56-1.42 (m, 8H). The specific preparation process is as follows:

[0065] Example 3: Synthesis of R-7 (trans,trans)-[1,1'-bicyclohexane]-4,4'-dicarboxylic acid (1.72 g, 6.77 mmol) was dissolved in 5 mL of thionyl chloride, and a catalytic amount of N,N-dimethylformamide was added, and the mixture was refluxed for 1 hour. The mixture was concentrated under reduced pressure, and the resulting mixture was recrystallized to obtain 1.3 g of colorless needle-shaped crystals of compound 3a with a yield of 66%.

[0066] Compound 1a (2.8 g, 5.25 mmol), compound 3a (0.73 g, 2.5 mmol), and N,N-diisopropylethylamine (0.68 g, 5.25 mmol) were dissolved in 60 mL of dichloromethane and reacted at room temperature for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 1.9 g of white solid compound 3b with a yield of 59%.

[0067] Compound 3b (1.9 g, 1.47 mmol), compound 1b (0.96 g, 3.23 mmol), and chromatic camphorsulfonic acid (0.68 g, 2.94 mmol) were dissolved in 20 mL of chloroform and reacted at 70 °C for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 1.8 g of white solid compound 3c with a yield of 66%.

[0068] Compound 3c (1.8 g, 0.97 mmol) and N,N-diisopropylethylamine (0.5 g, 3.88 mmol) were dissolved in 4 mL of dichloromethane, and acryloyl chloride (0.35 g, 3.88 mmol) was added dropwise under an ice-water bath, and reacted at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 1.5 g of white solid compound R-7 with a yield of 79%. 1H NMR (400 MHz, CDCl3) δ7.98 (s, 2H), 7.74 (s, 2H), 7.71-7.64 (m, 4H), 7.38-7.31 (m, 2H), 7.21-7.14(m, 2H), 7.13-7.06 (m, 4H), 6.99(d, J = 7.8 Hz, 4H), 6.88 (d, J = 7.8 Hz, 4H),6.44-6.35 (m, 4H), 6.17-6.05 (m, 4H), 5.84-5.75 (m, 4H), 4.52-4.45 (m, 4H),4.23-4.14 (m, 8H), 3.95 (t, J = 6.0 Hz, 4H), 3.91-3.84 (m, 4H), 3.66-3.61 (m,8H), 3.60-3.55 (m, 4H), 2.69-2.55 (m, 6H), 2.39-2.22 (m, 12H), 1.99-1.90 (m,4H), 1.84-1.56 (m, 20H), 1.55-1.42 (m, 8H), 1.27-1.10 (m, 6H). The specific preparation process is as follows:

[0069] Example 4: Synthesis of R-3 Compound 1a (1 g, 1.86 mmol), terephthaloyl chloride (0.18 g, 0.89 mmol), and N,N-diisopropylethylamine (0.34 g, 2.67 mmol) were dissolved in 20 mL of dichloromethane. The mixture was reacted at room temperature for 2 hours, and the resulting mixture was subjected to column chromatography and crystallization to obtain 0.84 g of white solid compound 4a with a yield of 80%.

[0070] Compound 4a (0.84 g, 0.48 mmol), compound 1b (0.32 g, 1.08 mmol), and chromatic camphorsulfonic acid (0.22 g, 0.96 mmol) were dissolved in 20 mL of chloroform and reacted at 70 °C for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.8 g of brown solid compound 4b with a yield of 96%.

[0071] Compound 4b (0.8 g, 0.45 mmol) and N,N-diisopropylethylamine (0.23 g, 1.8 mmol) were dissolved in 20 mL of dichloromethane, and acryloyl chloride (0.16 g, 1.8 mmol) was added dropwise under an ice-water bath, and reacted at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.62 g of white solid compound R-3, with a yield of 73%. 1 H NMR (400 MHz, CDCl3) δ8.44 (s, 4H), 8.14 (s, 2H), 7.79 (s, 2H), 7.68-7.62 (m, 4H), 7.36-7.29 (m,4H), 7.24-7.12 (m, 4H), 7.00 (d, J = 8.4 Hz, 4H), 6.89 (d, J = 8.4 Hz, 4H), 6.45-6.30 (m, 4H), 6.17-6.00 (m, 4H), 5.85-5.70 (m, 4H), 4.46-4.38 (m, 4H), 4.20-4.13 (m, 8H), 3.95 (t, J = 6.1 Hz, 4H), 3.85-3.77 (m, 4H), 3.59-3.54 (m, 4H), 3.53-3.41 (m, 8H), 2.74-2.57 (m, 4H), 2.41-2.29 (m, 8H), 1.86-1.67 (m, 16H),1.56-1.41 (m, 8H). The specific preparation process is as follows:

[0072] Example 5: Synthesis of R-8 (trans,trans)-[1,1'-bicyclohexane]-4,4'-dicarboxylic acid (6 g, 23.6 mmol), 2,5-dihydroxybenzaldehyde (6.85 g, 49.6 mmol), 4-dimethylaminopyridine (0.58 g, 4.72 mmol) were dissolved in 150 mL of dichloromethane. N,N'-diisopropylcarbodiimide (6.25 g, 49.6 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 10.5 g of white solid compound 5a with a yield of 90%.

[0073] Compound 5a (4.88 g, 9.9 mmol), trans-4-[4-(6-acryloyloxyhexyloxy)phenoxycarbonyl]cyclohexanecarboxylic acid (8.78 g, 21 mmol), and 4-dimethylaminopyridine (0.24 g, 2 mmol) were dissolved in 150 mL of dichloromethane. N,N'-diisopropylcarbodiimide (2.65 g, 21 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 7.9 g of white solid compound 5b with a yield of 62%.

[0074] Compound 5b (7.9 g, 6.1 mmol), compound 1b (4 g, 13.5 mmol), and chromatic camphorsulfonic acid (2.84 g, 12.3 mmol) were dissolved in 100 mL of chloroform. The mixture was reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 4 g of white solid compound 5c with a yield of 36%.

[0075] Compound 5c (4 g, 2.1 mmol) and N,N-diisopropylethylamine (1.11 g, 8.6 mmol) were dissolved in 50 mL of dichloromethane. Acryloyl chloride (0.78 g, 8.6 mmol) was slowly added dropwise under an ice-water bath and the mixture was allowed to react at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 2.5 g of white solid compound R-8 with a yield of 76%. 1 H NMR (500 MHz, CDCl3) δ 7.99 (s, 2H), 7.73 (s, 2H), 7.70 (d, J = 7.8 Hz, 2H), 7.66 (d, J = 8.0Hz, 2H), 7.37-7.32 (m, 2H), 7.20-7.15 (m, 2H), 7.14-7.06 (m, 4H), 6.98 (d, J =8.8 Hz, 4H), 6.88 (d, J = 8.9 Hz, 4H), 6.43-6.34 (m, 4H), 6.16-6.05 (m, 4H), 5.84-5.74 (m, 4H), 4.48 (t, J = 5.1 Hz, 4H), 4.22-4.13 (m, 8H), 3.94 (t, J = 6.3Hz, 4H), 3.88 (t, J= 5.5 Hz, 4H), 3.65-3.56 (m, 12H), 2.74-2.67 (m, 2H), 2.63-2.51 (m, 4H), 2.39-2.28 (m, 8H), 2.27-2.22 (m, 4H), 1.97-1.91 (m, 4H), 1.83-1.77 (m, 4H), 1.76-1.56 (m, 16H), 1.54-1.42 (m, 8H), 1.27-1.12 (m, 6H). The specific preparation process is as follows:

[0076] Example 6: Synthesis of R-14 Trans-1,4-cyclohexanedicarboxylic acid (15.6 g, 91 mmol), 2,5-dihydroxybenzaldehyde (26.3 g, 191 mmol), and 4-dimethylaminopyridine (1.1 g, 9.1 mmol) were dissolved in 150 mL of dichloromethane. N,N'-diisopropylcarbodiimide (25.2 g, 200 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 31.5 g of white solid compound 6a with a yield of 84%.

[0077] Compound 6a (31.5 g, 76.5 mmol), compound 6b (61 g, 160 mmol), and 4-dimethylaminopyridine (2.3 g, 19.3 mmol) were dissolved in 200 mL of dichloromethane. N,N'-diisopropylcarbodiimide (20 g, 160 mmol) was slowly added dropwise under an ice-water bath. The mixture was reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 32 g of white solid compound 6c with a yield of 37%.

[0078] Compound 6c (32 g, 28.1 mmol), compound 1b (18.4 g, 61.9 mmol), and chromatic camphorsulfonic acid (13 g, 56.2 mmol) were dissolved in 200 mL of chloroform and reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 37 g of white solid compound 6d with a yield of 77%.

[0079] Compound 6d (37 g, 21.8 mmol) and N,N-diisopropylethylamine (11.2 g, 87.2 mmol) were dissolved in 200 mL of dichloromethane. Acryloyl chloride (7.8 g, 87.2 mmol) was slowly added dropwise under an ice-water bath and the mixture was returned to room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 18.4 g of white solid compound R-14 with a yield of 47%. 1 H NMR (500MHz, CDCl3) δ7.79 (s, 2H), 7.78-7.66 (m, 4H), 7.54-7.41 (m, 4H), 7.38 (d, J =2.7 Hz, 2H), 7.07 (dd, J = 8.6, 2.8 Hz, 2H), 6.30-6.15 (m, 4H), 6.08-5.93 (m,4H), 5.83-5.70 (m, 4H), 4.31 (t, J = 4.8 Hz, 4H), 4.17-4.07 (m, 8H), 4.09-4.01(m, 4H), 3.97-3.91 (m, 4H), 3.72 (t, J = 4.8 Hz, 4H), 3.70-3.63 (m, 8H), 2.51-2.44 (m, 4H), 2.37-2.25 (m, 2H), 1.99-1.91 (m, 4H), 1.88-1.65 (m, 22H), 1.64-1.43 (m, 22H), 1.33-1.23 (m, 8H). The specific preparation process is as follows:

[0080] Example 7: Synthesis of R-11 Trans-1,4-cyclohexyldicarboxylic acid mono-tert-butyl ester (22.5 g, 100 mmol), 2,5-dihydroxybenzaldehyde (15 g, 110 mmol), and 4-dimethylaminopyridine (1.2 g, 10 mmol) were dissolved in 100 mL of dichloromethane. N,N'-diisopropylcarbodiimide (14 g, 110 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 31 g of white solid compound 7a with a yield of 89%.

[0081] Compound 7a (10 g, 28.7 mmol), compound 7b (9.4 g, 31.6 mmol), and 4-dimethylaminopyridine (0.35 g, 2.87 mmol) were dissolved in 200 mL of dichloromethane. N,N'-diisopropylcarbodiimide (4 g, 31.6 mmol) was slowly added dropwise under an ice-water bath. The reaction was allowed to proceed at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 11.5 g of white solid compound 7c with a yield of 64%.

[0082] Compound 7c (11.5 g, 18.3 mmol) was dissolved in 50 mL formic acid and 50 mL dichloromethane and reacted at 40 °C for 12 hours. Dichloromethane was added, and the mixture was washed with water and saturated brine, separated, and the organic phase was concentrated. The resulting mixture was subjected to column chromatography and crystallization to obtain 9.3 g of white solid compound 7d, with a yield of 89%.

[0083] Compound 7d (1 g, 1.75 mmol), hydroquinone (77 mg, 0.7 mmol), and 4-dimethylaminopyridine (17 mg, 0.14 mmol) were dissolved in 20 mL of dichloromethane. N,N'-diisopropylcarbodiimide (0.194 g, 1.54 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.85 g of white solid compound 7e with a yield of 99%.

[0084] Compound 7e (0.85 g, 0.7 mmol), compound 1b (0.46 g, 1.54 mmol), and chromatic camphorsulfonic acid (0.32 g, 1.4 mmol) were dissolved in 15 mL of chloroform and reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.9 g of white solid compound 7f with a yield of 75%.

[0085] Compound 7f (0.9 g, 0.51 mmol) and N,N-diisopropylethylamine (0.26 g, 2 mmol) were dissolved in 20 mL of dichloromethane. Acryloyl chloride (0.18 g, 2 mmol) was slowly added dropwise under an ice-water bath and the mixture was returned to room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.8 g of white solid compound R-11 with a yield of 84%. 1 H NMR (500 MHz, CDCl3) δ 7.97 (s, 2H), 7.74 (d, J = 2.1 Hz, 2H), 7.69 (d, J = 7.8 Hz, 2H), 7.66(d, J= 8.0 Hz, 2H), 7.37-7.32 (m, 2H), 7.20-7.15 (m, 2H), 7.15-7.03 (m, 8H), 6.45-6.35 (m, 4H), 6.17-6.05 (m, 4H), 5.86-5.76 (m, 4H), 4.47 (t, J = 5.4 Hz,4H), 4.23-4.18 (m, 8H), 4.16-4.10 (m, 4H), 3.87 (t, J = 5.6 Hz, 4H), 3.67-3.60(m, 8H), 3.59-3.54 (m, 4H), 2.70-2.60 (m, 6H), 2.42-2.25 (m, 14H), 2.20-2.12(m, 4H), 1.82-1.57 (m, 24H). The specific preparation process is as follows:

[0086] Example 8: Synthesis of R-15 Compound 7d (1 g, 1.75 mmol), 2,5-dihydroxybenzaldehyde (97 mg, 0.7 mmol), and 4-dimethylaminopyridine (17 mg, 0.14 mmol) were dissolved in 20 mL of dichloromethane. N,N'-diisopropylcarbodiimide (0.194 g, 1.54 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.87 g of white solid compound 8a with a yield of 99%.

[0087] Compound 8a (0.87 g, 0.7 mmol), compound 1b (0.69 g, 2.31 mmol), and chromatic camphorsulfonic acid (0.49 g, 2.1 mmol) were dissolved in 20 mL of chloroform and reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 1.2 g of white solid compound 8b with a yield of 88%.

[0088] Compound 8b (1.2 g, 0.58 mmol) and N,N-diisopropylethylamine (0.45 g, 3.48 mmol) were dissolved in 20 mL DCM. Acryloyl chloride (0.31 g, 3.48 mmol) was slowly added dropwise under an ice-water bath and the mixture was allowed to react at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.49 g of white solid compound R-15 with a yield of 38%. 1H NMR (500 MHz, CDCl3) δ 8.03-7.97 (m, 3H), 7.80-7.73 (m, 3H), 7.72-7.62 (m, 6H), 7.37-7.32(m, 3H), 7.20-7.15 (m, 3H), 7.15-7.06 (m, 6H), 6.46-6.33 (m, 5H), 6.18-6.03(m, 5H), 5.87-5.74 (m, 5H), 4.53-4.45 (m, 6H), 4.26-4.08 (m, 14H), 3.92-3.85(m, 6H), 3.67-3.55 (m, 18H), 2.77-2.62 (m, 6H), 2.42-2.27 (m, 14H), 2.20-2.13(m, 4H), 1.81-1.58 (m, 24H). The specific preparation process is as follows:

[0089] Example 9: Synthesis of R-5 Compound 7a (5 g, 14.4 mmol), trans-4-[4-(6-acryloyloxyhexyloxy)phenoxycarbonyl]cyclohexanecarboxylic acid (6 g, 14.4 mmol), and 4-dimethylaminopyridine (175 mg, 1.44 mmol) were dissolved in 50 mL of dichloromethane. N,N'-diisopropylcarbodiimide (2 g, 15.8 mmol) was slowly added dropwise under an ice-water bath and reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 9 g of white solid compound 9a with a yield of 84%.

[0090] Compound 9a (9 g, 12 mmol) was dissolved in 40 mL formic acid and 40 mL dichloromethane and reacted at 40 °C for 12 hours. Dichloromethane was added, and the mixture was washed with water and saturated brine, separated, and the organic phase was concentrated. The resulting mixture was subjected to column chromatography and crystallization to obtain 5.7 g of white solid compound 9b, with a yield of 69%.

[0091] Compound 9b (1 g, 1.45 mmol), hydroquinone (64 mg, 0.58 mmol), and 4-dimethylaminopyridine (14 mg, 0.12 mmol) were dissolved in 40 mL of dichloromethane. N,N'-diisopropylcarbodiimide (0.16 g, 1.27 mmol) was slowly added dropwise under an ice-water bath. The mixture was reacted at room temperature for 12 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.84 g of white solid compound 9c with a yield of 99%.

[0092] Compound 9c (0.84 g, 0.58 mmol), compound 1b (0.43 g, 1.45 mmol), and chromatic camphorsulfonic acid (0.27 g, 1.45 mmol) were dissolved in 50 mL of chloroform. The mixture was reacted at 70 °C for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.72 g of white solid 9d with a yield of 62%.

[0093] Compound 9d (0.72 g, 0.36 mmol) and N,N-diisopropylethylamine (0.18 g, 1.44 mmol) were dissolved in 20 mL of dichloromethane. Acryloyl chloride (0.13 g, 1.44 mmol) was slowly added dropwise under an ice-water bath, and the mixture was allowed to react at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 0.6 g of light yellow solid compound R-13 with a yield of 79%. 1 H NMR (500MHz, CDCl3) δ 7.99 (s, 2H), 7.75 (s, 2H), 7.70 (d, J = 7.9 Hz, 2H), 7.66 (d, J =8.0 Hz, 2H), 7.37-7.32 (m, 2H), 7.20-7.15 (m, 2H), 7.15-7.05 (m, 8H), 6.98(d, J = 8.9 Hz, 4H), 6.88 (d, J = 9.0 Hz, 4H), 6.43-6.34 (m, 4H), 6.17-6.06 (m,4H), 5.85-5.74 (m, 4H), 4.48 (t, J = 5.3 Hz, 4H), 4.22-4.15 (m, 8H), 3.94 (t, J =6.4 Hz, 4H), 3.88 (t, J = 5.5 Hz, 4H), 3.67-3.55 (m, 12H), 2.74-2.57 (m, 8H), 2.39-2.29 (m, 16H), 1.82-1.66 (m, 24H), 1.54-1.43 (m, 8H). The specific preparation process is as follows:

[0094] Example 10: Synthesis of R-9 Compound 1a (4.2 g, 7.8 mmol), trans-1,4-bis(methylsulfonyloxymethyl)cyclohexane (1 g, 3.7 mmol), potassium phosphate (1.7 g, 7.8 mmol) were dissolved in 40 mL N,N-dimethylformamide, reacted at 80 °C for 8 hours, and returned to room temperature. Dichloromethane was added, washed with water and saturated brine, separated, and the organic phase was concentrated. The resulting mixture was subjected to column chromatography and crystallization to obtain 2.4 g of white solid compound 10a, with a yield of 55%.

[0095] Compound 10a (2.4 g, 2 mmol), compound 1b (1.3 g, 4.4 mmol), and chromatic camphorsulfonic acid (0.93 g, 4 mmol) were dissolved in 40 mL of chloroform and reacted at 70 °C for 2 hours. The resulting mixture was subjected to column chromatography and crystallization to obtain 2.3 g of white solid compound 10b with a yield of 66%.

[0096] Compound 10b (2.3 g, 1.3 mmol) and N,N-diisopropylethylamine (0.67 g, 5.2 mmol) were dissolved in 20 mL of dichloromethane, and acryloyl chloride (0.47 g, 5.2 mmol) was added dropwise under an ice-water bath, and reacted at room temperature for 1 hour. The resulting mixture was subjected to column chromatography and crystallization to obtain 1.7 g of white solid compound R-9, with a yield of 71%. 1 H NMR (500 MHz, CDCl3) δ8.00 (s, 2H), 7.72-7.65 (m, 4H), 7.60 (d, J = 2.1 Hz, 2H), 7.37-7.32 (m, 2H),7.20-7.15 (m, 2H), 7.08-6.85 (m, 12H), 6.44-6.35 (m, 4H), 6.17-6.05 (m, 4H),5.85-5.75 (m, 4H), 4.48 (t, J = 5.4 Hz, 4H), 4.24-4.15 (m, 8H), 3.95 (t, J = 6.4Hz, 4H), 3.92-3.85 (m, 6H), 3.67-3.61 (m, 10H), 3.61-3.57 (m, 4H), 2.72-2.60(m, 4H), 2.43-2.28 (m, 12H), 1.90-1.66 (m, 22H), 1.56-1.41 (m, 8H). The specific preparation process is as follows:

[0097] Example 11: Composition of Liquid Crystal Composition 1 Preparation of liquid crystal composition: Taking Example 11 as an example, R-1, N-1, OXE-03, and BYK-354 were weighed and mixed according to the corresponding weight proportions, and corresponding mass proportions of cyclopentanone and N-methylpyrrolidone were added, stirred and dissolved completely at 50°C, and cooled to room temperature for use.

[0098]

[0099] Example 12: Composition of Liquid Crystal Composition 2

[0100] Example 13: Composition of Liquid Crystal Composition 1

[0101] Example 14: Composition of Liquid Crystal Composition 1

[0102] Example 15: Composition of Liquid Crystal Composition 1

[0103] Comparative Example 1: Composition of Composition 1

[0104] Monomer RC-1 is:

[0105] Comparative Example 2: Composition of Composition 2

[0106] Monomer RC-2 is:

[0107] Performance Test: (1) Obtaining phase difference film Preparation of phase difference film Wash the 10*10cm optical glass and evenly coat the optical alignment agent HSPA-252B (manufactured by Osaka Organic Co., Ltd.) on the glass surface using a spin coater (2300rpm, 10s). Then dry at 120℃. After cooling to room temperature, irradiate the surface with 313nm polarized ultraviolet light for 10mJ to obtain a glass substrate with an alignment layer.

[0108] On a glass substrate with an alignment layer, the above Examples 11-15 and Comparative Examples 1-2 were uniformly coated using a spin coater (600 rpm, 30 s), and the solvent was dried to evaporate. The drying temperature was slightly lower than the clearing point temperature shown in the above table. Then, the film surface with the composition was 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, a phase difference film is obtained.

[0109] (2) Color dispersion test The polarization measuring instrument Axoscan was used to test the phase difference of the phase difference film at each wavelength, and the phase difference R450 at 450nm and the phase difference R550 at 550nm were taken. The color dispersion value was obtained by calculating R450 / R550. The test results are shown in the following table:

[0110] Examples 11 to 15 and Comparative Example 1 all use 85 parts of reverse wavelength dispersion monomers and 15 parts of positive wavelength dispersion monomers N-1. Examples 11 to 14 use the monomers of the scheme proposed by the present invention, and the color dispersion R450 / 550 is all below 0.906. Comparative Example 1 shows a monomer in the prior art with 5 main chain six-membered ring monomers and 1 side chain chromophore group per molecule. Its chromophore group is the same as that of the example, but the color dispersion R450 / 550 is the highest. It can be seen that the use of a longer liquid crystal main chain and a dense arrangement of chromophore groups is helpful to improve color dispersion. Example 15 is a mixture of the monomers of the scheme proposed by the present invention and RC-1, and its color dispersion can also be improved to a certain extent.

[0111] Comparative Example 2 shows a reverse wavelength dispersion monomer with 3 main chain six-membered ring monomers and 1 side chain chromophore unit / molecule. In this case, the liquid crystal system cannot be effectively aligned, so the color dispersion R450 / 550 cannot be measured.

[0112] (3) △n test Use polarization measuring instrument Axoscan to test the phase difference of a fixed point on the phase difference film at 550nm to obtain R550 at that point. Then use tape to remove a part of the film surface, and use white light interferometer (Filmetrics Profilm 3D) to scan the torn edge to obtain the film thickness d at the cross section. The △n at that point is calculated according to the following formula: △n=R550 / d.

[0113]

[0114] It can be seen that the use of the monomers proposed in the present invention is helpful to improve the △n value of the optical film, which is a reflection of the orderliness of the liquid crystal arrangement.

[0115] (4) Response completion test The film was transferred from glass to TAC substrate and scanned using a Fourier transform infrared spectrometer (Bruker APLHA II) in attenuated total reflectance (ATR) mode. The obtained spectrum was based on the acrylate peak (810 cm -1 The degree of disappearance of the acrylate peak is used to calculate the completion of the photochemical reaction. The disappearance of the acrylate peak is a common method to determine the completion of the photochemical reaction. The reference document is Simon, J. and Langenscheidt, A. (2020) 'Curing behavior of a UV-curable inkjet ink: Distinction between surface-cure and deep-cureperformance', Journal of Applied Polymer Science, 137(40), pp. 1–9.

[0116]

[0117] It can be seen that the use of the monomers proposed in the present invention is helpful to improve the photocuring completion of the optical film.

[0118] It should also be noted that the terms "include", "comprises" or any other variations thereof are intended to cover non-exclusive inclusion, so that a process, method, commodity or device including a series of elements includes not only those elements, but also other elements not explicitly listed, or also includes elements inherent to such process, method, commodity or device. In the absence of more restrictions, the elements defined by the sentence "comprises a ..." do not exclude the existence of other identical elements in the process, method, commodity or device including the elements.

[0119] The above is only an embodiment of the present application and is not intended to limit the present application. For those skilled in the art, the present application may have various changes and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of the claims of the present application.

Claims

1. A liquid crystal compound, characterized in that: The structure of the liquid crystal compound satisfies the general formula (I): （I）； In the general formula (I), 3≤x≤10, 2≤y≤5, wherein x is a positive integer, and y is a positive integer; In the general formula (I), A1 represents , the two bonding positions on A1 can be arbitrarily reversed, where 0≤m1+m2+m3≤15, m1 is a positive integer, m2 is a positive integer, and m3 is a positive integer; -CH2-, -O-, and -COO- in A1 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A1 can be arbitrarily selected to be positive or negative; In the general formula (I), A2 represents , the two bonding positions on A2 can be arbitrarily reversed, where 0≤n1+n2+n3≤15, n1 is a positive integer, n2 is a positive integer, and n3 is a positive integer; -CH2-, -O-, and -COO- in A2 can be arranged in any order except to form -OO-, and the direction of the ester bond represented by -COO- in A2 can be arbitrarily selected to be positive or negative; In the general formula (I), L1~L x Each independently selected from a single bond, , , , , , , , The two bonding positions on the can be reversed at will; In the general formula (I), G1~G x Each is independently selected from 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,3-dioxane-2,5-diyl; G1~G x The two bonding positions on the G1~G x The H on the is unsubstituted or substituted by one or more substituents Sp1; Sp1 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp1 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp1 can be replaced by a fluorine atom; In the general formula (I), R1 and R2 are each independently selected from a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, , , , or Group; In the general formula (I), Ar1~Ar y is a 5- to 10-membered aromatic ring or aromatic heterocyclic ring; Ar1~Ar y The H on the SG1~SG y Substituted or substituted by one or more substituents Sp2; Sp2 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp2 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp2 can be replaced by a fluorine atom; In the general formula (I), M1~M y Each independently selected from a single bond, , , , , M1~M y The two bonding positions on the can be reversed at will; In the general formula (I), SG1~SG y The structure is the general formula (II): (II); In the general formula (II), J1~J y each independently selected from a single bond, -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -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=C H-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-, -C≡C-, , ,or , J1~J y The two bonding positions on the top have no left or right direction regulations and can be selected arbitrarily; Among them, Q is used Indicates that T1 is selected from , The two bonding positions on the ester bond can be arbitrarily reversed; 0≤p1+p2+p3≤16, p1 is a positive integer, p2 is a positive integer, and p3 is a positive integer; -CH2-, -O-, and -COO- in T1 can be arranged in any order except for forming -OO-, and the direction of the ester bond represented by -COO- in T1 can be arbitrarily selected to be positive or negative; R3 is selected from hydrogen atom, methyl, ethyl, methoxy, , , , , Group; In the general formula (II), E1~E y Each independently selected from a single bond, (1≤q≤5), , , , , , ; E1~E y The two bonding positions on the top have no left or right regulations and can be selected arbitrarily; E1~E y is unsubstituted or substituted by one or more substituents Sp3; Sp3 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp3 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp3 can be replaced by a fluorine atom; In the general formula (II), Z1~Z y is a 5- to 14-membered aromatic ring or aromatic heterocyclic ring; Z1~Z y The H on the molecule is unsubstituted or can be substituted by one or more substituents Sp4. Replace, and E1~E y Link; Sp4 is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl chain having 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- in the alkyl chain selected from Sp4 can be 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-, and any hydrogen atom in the alkyl chain selected from Sp4 can be replaced by a fluorine atom; In, T2 is selected , Where r is 0 to 10, R4 is selected from methyl, ethyl, methoxy, , , , , Group.

2. The liquid crystal compound according to claim 1, characterized in that M1~M y Each independently selected from .

3. The liquid crystal compound according to claim 1, characterized in that In SG1~SG y In the general structural formula (II), J1~J y Selected from , when E is a single bond and Z is a benzothiazole group, p2+p3≠0 in Q.

4. The liquid crystal compound according to claim 1, characterized in that SG1~SG y The structural formula is: 。 5. A liquid crystal composition, characterized in that: include: The liquid crystal compound or polymerizable liquid crystal compound according to any one of claims 1 to 4.

6. The liquid crystal composition according to claim 5, characterized in that: The liquid crystal composition comprises: a liquid crystal compound in an amount of 5 parts by weight or more and a polymerizable liquid crystal compound in an amount of 5 parts by weight or more.

7. The liquid crystal composition according to claim 6, characterized in that: The liquid crystal composition comprises: 50 to 90 parts by weight of a liquid crystal compound and 10 to 50 parts by weight of a polymerizable liquid crystal compound.

8. The liquid crystal composition according to claim 5, characterized in that: The polymerizable liquid crystal compound is selected from the following structures: 。 9. A phase difference film, characterized in that: The phase difference film is formed by polymerizing the liquid crystal composition described in any one of claims 5 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 are R450 / R550≤1.0.

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