Liquid crystal compounds, liquid crystal compositions comprising the same and applications

Abstract

This invention discloses a liquid crystal compound, a liquid crystal composition comprising the same, and its applications. The liquid crystal compound is selected from compounds represented by Formula I. Wherein, R1 represents [missing information], and X1 and X2 independently represent -OH and -OR, respectively. W -NH2, -NHR W -COOH, -SH or -SR W Sp2 represents an alkenyl group with 2-10 carbon atoms. Liquid crystal compositions containing this compound exhibit excellent alignment properties, strong pretilt angle stability, compatibility with different materials, high VHR, and moderately sized and relatively flat particles after polymerization, resulting in higher contrast for the display panel. Ⅰ.

Description

Technical Field

[0001] This invention relates to the field of liquid crystal display technology. More specifically, it relates to a liquid crystal compound, a liquid crystal composition comprising the same, and its applications. Background Technology

[0002] PSVA (Polymer Stabilized Vertical Alignment) liquid crystal technology is an advanced liquid crystal display technology. It achieves stable display results by adding polymerizable monomers to liquid crystal molecules and curing them with ultraviolet light to form a polymer, thus fixing the pretilt angle of the liquid crystal molecules. Compared to traditional VA (vertical alignment) technology, PSVA technology has significant advantages such as faster response time, higher contrast ratio, wider viewing angle, and higher transmittance. In recent years, the penetration rate of PSVA technology in the high-resolution panel market has been continuously increasing, especially in the 8K panel field. With the continuous advancement of display technology, PSVA liquid crystal technology will continue to have broad application prospects in the future display market. On the one hand, with the rapid development of emerging technologies such as 5G communication, the Internet of Things, and artificial intelligence, the demand for display devices will continue to increase. PSVA technology, with its excellent display performance and lower manufacturing cost, is expected to continue to maintain its leading position in the field of large-size, high-resolution displays. On the other hand, PSVA technology is also undergoing continuous technological innovation and optimization, such as improving pixel structure, optimizing UV curing conditions, and improving the performance of liquid crystal materials, to further improve display effects and production efficiency.

[0003] Traditional PSVA liquid crystal display technology typically relies on a polyimide (PI) alignment layer to achieve the initial orientation of liquid crystal molecules. However, the use of PI alignment layers has some limitations, such as complex manufacturing processes, high costs, and susceptibility to defects caused by friction. Therefore, PI-less (polyimide-free alignment layer) technology has gradually gained attention. PI-less technology simplifies the manufacturing process, reduces costs, and improves product stability and reliability by employing novel alignment materials and processes that eliminate the need for a PI alignment layer. As the technology matures, PI-less technology is expected to gain a certain share of the future liquid crystal display market, especially in high-end display devices and emerging application areas. Despite the numerous potential advantages of PI-less technology, several technical challenges remain in practical applications: ① Alignment stability: Ensuring stable orientation of liquid crystal molecules under different operating conditions (such as temperature changes and voltage fluctuations) without a PI alignment layer is a problem that urgently needs to be solved; ② Material compatibility: New alignment materials need to have good compatibility with existing liquid crystal materials and other display materials to ensure display performance and device stability; ③ Optical performance, such as contrast ratio, response time, and viewing angle, are key factors affecting its widespread application.

[0004] Therefore, developing a compound that can be stably aligned under different working conditions is a pressing technical problem that needs to be solved. Summary of the Invention

[0005] In view of the above problems, the purpose of this invention is to provide a liquid crystal compound, a liquid crystal composition containing the same, and its application. This technical solution effectively solves the aforementioned technical defects. The liquid crystal composition containing the liquid crystal compound has good alignment effect and strong pretilt angle stability, while also ensuring compatibility with different materials, maintaining a high VHR, and producing particles of moderate size and relatively flat surface after polymerization, resulting in higher contrast for the display panel.

[0006] To achieve the above objectives, the present invention adopts the following technical solution:

[0007] On one hand, the present invention provides a liquid crystal compound, said liquid crystal compound being selected from compounds represented by Formula I.

[0008] Ⅰ

[0009] in,

[0010] , , , Each group independently represents an aromatic ring, heteroaromatic ring, aliphatic ring, or fused ring, wherein one or more H atoms in these groups may optionally be substituted with L;

[0011] L represents -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally replaced by -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally replaced by halogens;

[0012] R2 represents an alkyl group having at most 15 carbon atoms, an alkenyl group having at most 15 carbon atoms, or an alkynyl group having at most 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens;

[0013] R1 indicates ;

[0014] X1 and X2 independently represent -OH and -OR, respectively. W -NH2, -NHR W -COOH, -SH, or -SR W ;

[0015] R W Indicates a straight-chain or branched alkyl group having 1-5 carbon atoms;

[0016] Sp1, Sp3, Sp5, Sp6, Z1, Z2, and Z3 each independently represent a single bond, an alkylene group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an ynylene group having up to 15 carbon atoms; wherein one or more non-adjacent -CH2- atoms in these groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with F or Cl;

[0017] Sp2 represents an alkenyl group with 2-10 carbon atoms;

[0018] Sp4 indicates a tetravalent group;

[0019] a and b each represent 0 or 1 independently;

[0020] P1 represents a polymerizable group.

[0021] In a second aspect, the present invention provides a liquid crystal composition comprising one or more liquid crystal compounds as described in the first aspect above.

[0022] Thirdly, the present invention provides a liquid crystal display element or liquid crystal display, wherein the liquid crystal display element or liquid crystal display comprises the liquid crystal composition as described in the second aspect above, wherein...

[0023] The liquid crystal display element is an active matrix display element or a passive matrix display element; or

[0024] The liquid crystal display is an active matrix display or a passive matrix display.

[0025] The beneficial effects of this invention are as follows:

[0026] The liquid crystal compound (the compound shown in Formula I) provided by this invention can be used as an alignment agent. In the structure of this liquid crystal compound, a sterically hindered alkene-containing structure is introduced at appropriate positions of the alignment groups. This allows it to chemically bond with planarization layer materials after UV irradiation. Compared to alignment agents that only have polar groups such as -OH and -NH, it exhibits better alignment effects, stronger pretilt angle stability, and ensures compatibility with different materials, maintaining a high VHR. Furthermore, the particles after polymerization are of moderate size and have relatively flat surfaces, resulting in higher contrast for the display panel. Attached Figure Description

[0027] The specific embodiments of the present invention will be described in further detail below with reference to the accompanying drawings.

[0028] Figure 1 The mass spectrum of the compound represented by Formula I2-15 is shown. Detailed Implementation

[0029] To more clearly illustrate the present invention, the following description, in conjunction with preferred embodiments and accompanying drawings, further explains the invention. Similar components in the drawings are indicated by the same reference numerals. Those skilled in the art should understand that the specific description below is illustrative rather than restrictive and should not be construed as limiting the scope of protection of the present invention.

[0030] According to a specific embodiment of the present invention, a liquid crystal compound is provided, said liquid crystal compound being selected from compounds represented by Formula I.

[0031] Ⅰ

[0032] in,

[0033] , , , Each group independently represents an aromatic ring, heteroaromatic ring, aliphatic ring, or fused ring, wherein one or more H atoms in these groups may optionally be substituted with L;

[0034] L represents -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally replaced by -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally replaced by halogens;

[0035] R2 represents an alkyl group having at most 15 carbon atoms, an alkenyl group having at most 15 carbon atoms, or an alkynyl group having at most 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens;

[0036] R1 indicates ;

[0037] X1 and X2 independently represent -OH and -OR, respectively. W -NH2, -NHR W -COOH, -SH, or -SR W ;

[0038] R W Indicates a straight-chain or branched alkyl group having 1-5 carbon atoms;

[0039] Sp1, Sp3, Sp5, Sp6, Z1, Z2, and Z3 each independently represent a single bond, an alkylene group having at most 15 carbon atoms, an alkenyl group having at most 15 carbon atoms, or an alkynyl group having at most 15 carbon atoms; wherein one or more non-adjacent -CH2- atoms in these groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- are not directly connected to each other, and one or more H atoms in these groups are optionally replaced by F or Cl;

[0040] Sp2 represents an alkenyl group with 2-10 carbon atoms;

[0041] Sp4 indicates a tetravalent group;

[0042] a and b each represent 0 or 1 independently;

[0043] P1 represents a polymerizable group.

[0044] In this embodiment, the liquid crystal compound can be used as a self-aligning agent. The liquid crystal compound has specific groups (R1) in its structure, which gives the liquid crystal composition containing the compound good alignment effect, good contrast, pretilt angle stability, and reliability.

[0045] This invention discloses a liquid crystal display with vertical alignment and no alignment layer.

[0046] In this embodiment, the alkyl group having up to 15 carbon atoms can be a straight-chain alkyl group, a branched alkyl group, or a cyclic alkyl group having up to 15 carbon atoms.

[0047] In this embodiment, the alkylene group having up to 15 carbon atoms can be a straight-chain alkylene group, a branched alkylene group, or a cyclic alkylene group having up to 15 carbon atoms.

[0048] For example, an alkylene group having up to 15 carbon atoms is, for instance, a straight-chain alkylene group having 4 carbon atoms has the structure: -(CH2)4-.

[0049] For example, an alkenyl group having at most 15 carbon atoms is, for instance, an alkenyl group having 3 carbon atoms has the structure: -CH2-CH=CH-.

[0050] For example, an alkynyl group having up to 15 carbon atoms is, for instance, an alkynyl group having 3 carbon atoms has the structure: -CH2-C≡C-.

[0051] In some examples, the alkenyl group having 2-10 carbon atoms includes, but is not limited to, -(CH2)2-CH=CH2, -CH2-CH=CH2, -(CH2)2-CH=CH-CH3, -CH2-CH=CH-CH3, etc.

[0052] In some examples, the tetravalent group is selected from... .

[0053] In some examples, the halogen is selected from F, Cl, or Br.

[0054] In some examples, the polymerizable group includes, but is not limited to, acrylate groups, methacrylate groups, etc.

[0055] In some examples, the , , , Each represents independently , , , , , , , or In these groups, one or more H atoms may optionally be replaced by L;

[0056] X1 and X2 each represent -OH independently.

[0057] In some examples, the compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I1 to I11 below.

[0058] Ⅰ1、 Ⅰ2、

[0059] Ⅰ3、 Ⅰ4、

[0060] Ⅰ5、 Ⅰ6、

[0061] Ⅰ7、 Ⅰ8、

[0062] Ⅰ9、 Ⅰ10、

[0063] Ⅰ11;

[0064] in,

[0065] r1, r2, r3, and r4 each independently represent 0, 1, 2, or 3;

[0066] L1, L2, L3, and L4 each independently represent -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens; and at least one of L1, L2, L3, and L4 is -Sp1-P1.

[0067] That is, all compounds represented by formulas I1 to I11 contain at least one -Sp1-P1 group. For example, in the compound represented by formula I1, at least one of L1, L2, L3, and L4 is -Sp1-P1; in the compound represented by formula I4, at least one of L1, L2, and L3 is -Sp1-P1; and in the compound represented by formula I6, at least one of L1 and L2 is -Sp1-P1.

[0068] In some preferred examples, the compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I1' to I11'.

[0069] Ⅰ1'、 Ⅰ2'、

[0070] Ⅰ3'、 Ⅰ4'、

[0071] Ⅰ5'、 Ⅰ6'、

[0072] Ⅰ7'、 Ⅰ8'、

[0073] Ⅰ9'、 Ⅰ10'、

[0074] Ⅰ11';

[0075] Among them, at least one of L1 and L2 is -Sp1-P1.

[0076] That is, among the compounds shown in Formula I1' to Formula I11', if the compound contains both L1 and L2, then at least one of L1 and L2 is -Sp1-P1; if the compound contains only L1, then at least one of L1 is -Sp1-P1.

[0077] In some more specific examples, the compounds represented by Formula I are selected from the group consisting of compounds represented by Formulas I1-1 to I11-1 below.

[0078]

[0079] In some examples, the compounds represented by Formula I of the present invention can be synthesized according to the following scheme.

[0080]

[0081] Where n = 0 or 1;

[0082] R11 express ;

[0083] L 11 L 12 Each of the following groups independently represents -H, -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens;

[0084] R represents H or an alkyl group with up to 7 carbon atoms;

[0085] The definitions of R2 and a are the same as those described above.

[0086] In the above reactions, preparation In the steps, when n=0, the reaction in this step involves a low-temperature lithiation reaction using n-butyllithium, followed by the addition of trimethyl borate, hydrolysis to obtain boric acid, and then oxidation of boric acid with hydrogen peroxide to obtain phenol; when n=1, this step also involves a low-temperature lithiation reaction using n-butyllithium, followed by the addition of DMF, hydrolysis to obtain an aldehyde, and then reduction of the aldehyde with potassium borohydride to obtain an alcohol. Or

[0087] The compound represented by Formula I of the present invention can be synthesized according to the following scheme.

[0088]

[0089] In the above reaction,

[0090] R 11 express ;

[0091] L 11 L 12 Each of the following groups independently represents -H, -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens;

[0092] R represents H or an alkyl group with up to 7 carbon atoms;

[0093] The definitions of R2 and a are the same as those described above.

[0094] The raw materials and reagents used in the synthesis can be obtained through conventional synthesis or commercial channels. The principles, operation procedures, routine post-processing, silica gel column chromatography, recrystallization purification, and other techniques of this method are well known to synthesizers in this field, and the synthesis process can be fully realized to obtain the target product.

[0095] All reactions in all steps of the above methods are carried out in a solvent; the solvent is selected from at least one of tetrahydrofuran, N,N-dimethylformamide, ethanol, methanol, dichloromethane, acetone, toluene and deionized water.

[0096] According to another specific embodiment of the present invention, a liquid crystal composition is provided, the liquid crystal composition comprising one or more liquid crystal compounds as described above.

[0097] In some examples, the liquid crystal composition contains 0.1 to 2% of the compound represented by Formula I by weight. In some more specific examples, the content of the compound represented by Formula I in the liquid crystal composition includes, but is not limited to, 0.3 to 1.7%, 0.3 to 1.5%, 0.4 to 1.2%, etc.

[0098] In some examples, the liquid crystal composition also contains 0 to 2% polymerizable compound by weight percentage.

[0099] In some more specific examples, the content of the polymerizable compound in the liquid crystal composition includes, but is not limited to, 0, 0.1-2%, 0.1-1.5%, 0.3-1.2%, 0.1-1%, 0.1-0.5%, etc.

[0100] In some examples, the liquid crystal composition contains 0.3 to 1.5% by weight of the compound represented by Formula I and 0.1 to 1.5% by weight of the polymerizable compound.

[0101] In some preferred embodiments, the liquid crystal composition contains at least one compound selected from those shown in formulas I2, I5, and I7. Liquid crystal compositions containing these compounds exhibit better alignment and superior solubility.

[0102] In some specific examples, the liquid crystal composition contains at least one compound selected from the aforementioned formulas I2', I5' and I7'.

[0103] In some preferred embodiments, the compound represented by Formula I in the liquid crystal composition is selected from at least one of the compounds represented by Formulas I1-1, I2-13, I2-15, I3-3, I5-11, I6-1, I7-1, I8-2, and I9-1. Liquid crystal compositions containing at least one of these compounds exhibit better alignment and superior solubility, and the resulting liquid crystal compositions show relatively better reaction rates and pretilt angle stability.

[0104] In some more preferred examples, the compound represented by Formula I in the liquid crystal composition is selected from at least one of the compounds represented by Formulas I2-13, I2-15, I5-11 and I7-1.

[0105] In some examples, the polymerizable compound is selected from the group consisting of compounds represented by the following formulas RM-1 to RM-7.

[0106] RM-1 RM-2,

[0107] RM-3 RM-4

[0108] RM-5 RM-6

[0109] RM-7.

[0110] In some examples, the liquid crystal composition contains at least two polymerizable compounds selected from those shown in formulas RM-1 to RM-7. Under these conditions, the resulting liquid crystal composition exhibits superior contrast, pretilt angle stability, and reliability.

[0111] In some examples, the liquid crystal composition further comprises one or more compounds represented by Formula II.

[0112] II

[0113] in,

[0114] R3 and R4 each independently represent straight-chain or branched alkyl groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, or alkoxy groups with 1-10 carbon atoms;

[0115] m1 represents 1, 2, or 3;

[0116] , Each represents independently , , or When m1 represents 2 or 3, They are either the same or different independently.

[0117] In some examples, the compound represented by Formula II is selected from the group consisting of the compounds represented by Formulas II-1 to II-8 below.

[0118] II-1 II-2

[0119] II-3 II-4

[0120] II-5 II-6

[0121] II-7 II-8;

[0122] in,

[0123] R 31 R 41 Each can be independently represented as a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms.

[0124] In some examples, the content of the compound represented by Formula II in the liquid crystal composition, by mass percentage, includes, but is not limited to, 10-70%, 19-60%, 20-60%, 30-50%, 25-45%, etc.

[0125] In some examples, the liquid crystal composition further comprises one or more compounds represented by Formula III.

[0126] III

[0127] in,

[0128] R5 and R6 each independently represent a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropyl, cyclobutyl, or cyclopentyl.

[0129] Z represents a single bond, -CH2O-, -CH2CH2-, or -CH=CH-;

[0130] m2 represents 1, 2, or 3;

[0131] , Each represents independently , , , or ,and , At least one of them represents When m2 represents 2 or 3, They are either the same or different independently.

[0132] In some specific examples, the compound represented by Formula III is selected from the group consisting of compounds represented by Formulas III-1 to III-13.

[0133] Ⅲ-1、 Ⅲ-2、

[0134] Ⅲ-3、 Ⅲ-4、

[0135] Ⅲ-5、 Ⅲ-6、

[0136] Ⅲ-7、 Ⅲ-8、

[0137] Ⅲ-9、 Ⅲ-10、

[0138] Ⅲ-11、 Ⅲ-12、

[0139] Ⅲ-13;

[0140] in,

[0141] R 51 R 61 Each of these groups independently represents a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropylene, cyclobutylene, or cyclopentylene.

[0142] In some examples, the content of the compound represented by Formula III in the liquid crystal composition, by mass percentage, includes, but is not limited to, 20-80%, 30-80%, 40-70%, 50-70%, etc.

[0143] In some examples, the liquid crystal composition further comprises one or more compounds of formula IV.

[0144] IV

[0145] in,

[0146] R7 and R8 each independently represent a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropylene, cyclobutylene, or cyclopentylene.

[0147] W represents -O-, -S-, or -CH2O-.

[0148] In some examples, the content of the compound represented by Formula IV in the liquid crystal composition, by mass percentage, includes, but is not limited to, 0, 0-15%, 1-15%, 1-10%, 1-5%, etc.

[0149] In some specific examples, the liquid crystal composition comprises: at least one compound represented by Formula I,

[0150] At least one compound represented by Formula II, and

[0151] At least one compound represented by Formula III and / or Formula IV.

[0152] In some preferred examples, the liquid crystal composition comprises:

[0153] At least one compound represented by Formula I,

[0154] At least one polymerizable compound selected from compounds represented by formulas RM-1, RM-2, RM-4, and RM-5,

[0155] At least one compound represented by Formula II, and

[0156] At least one compound represented by Formula III and / or Formula IV.

[0157] In some more specific preferred examples, the liquid crystal composition comprises:

[0158] At least one compound of formula I, selected from compounds of formulas I1-1, I2-13, I2-15, I3-3, I5-11, I6-1, I7-1, I8-2, and I9-1.

[0159] At least one polymerizable compound selected from compounds represented by formulas RM-1, RM-2, RM-4, and RM-5,

[0160] At least one compound represented by Formula II, and

[0161] At least one compound represented by Formula III and / or Formula IV.

[0162] In some preferred embodiments, the liquid crystal composition comprises, by weight percentage: 0.4–1.2% of the compound represented by Formula I, 0.1–0.7% of the polymerizable compound, 19–60% of the compound represented by Formula II, 30–80% of the compound represented by Formula III, and 0–15% of the compound represented by Formula IV. The liquid crystal composition obtained under these conditions exhibits superior alignment and solubility, and PI-less display devices containing it demonstrate better reliability.

[0163] Various functional dopants can also be added to the liquid crystal compound of the present invention. The dopant content is preferably between 0.005% and 1%. Examples of such dopants include antioxidants, ultraviolet absorbers, and chiral agents.

[0164] Exemplary antioxidants include, but are not limited to:

[0165]

[0166]

[0167] Where t represents an integer from 1 to 10.

[0168] Exemplary chiral agents (levorotatory or dextrorotatory) include, but are not limited to:

[0169] ,

[0170] , ,

[0171] , .

[0172] According to another specific embodiment of the present invention, a liquid crystal display element or liquid crystal display is provided, comprising the liquid crystal composition as described above, wherein,

[0173] The liquid crystal display element is an active matrix display element or a passive matrix display element; or

[0174] The liquid crystal display is an active matrix display or a passive matrix display.

[0175] For example, the liquid crystal display element or liquid crystal display preferably does not have an alignment layer, especially not a polyimide layer for vertical alignment of the liquid crystal.

[0176] Example

[0177] The technical solution of the present invention will be described below with reference to some specific embodiments.

[0178] In this invention, the preparation methods are all conventional unless otherwise specified, and the raw materials used can be obtained from publicly available commercial sources unless otherwise specified. The reaction process is generally monitored by TLC. The post-reaction treatment generally includes water washing, extraction, drying after combining organic phases, solvent removal under reduced pressure, recrystallization, and column chromatography. Those skilled in the art can implement this invention according to the following description.

[0179] All percentages in this instruction manual refer to mass percentages, and temperatures are in degrees Celsius (°C). The specific meanings of other symbols and test conditions are as follows:

[0180] Tni represents the liquid crystal clearing point (°C), measured by DSC quantitative method;

[0181] Δn represents optical anisotropy, Δn = n e -n o , where n o Let n be the refractive index of ordinary light. e The refractive index of unusual light was measured at 25±2℃, 589nm, using an Abbe refractometer.

[0182] Δε represents dielectric anisotropy, Δε = ε ∥ -ε ⊥ , where ε ∥ ε is the dielectric constant parallel to the molecular axis. ⊥ The dielectric constant is perpendicular to the molecular axis. The test conditions are 25±0.5℃, 20-micron vertical cell, and INSTEC:ALCT-IR1 test.

[0183] γ1 represents rotational viscosity (mPa·s), and the test conditions are 25±0.5℃, 20-micron vertical cell, INSTEC:ALCT-IR1 test;

[0184] K 11 K is the elastic constant of the development. 33 The bending elastic constant was determined under the following test conditions: 25°C, INSTEC:ALCT-IR1, and a 20-micron vertical box.

[0185] Backlight brightness is 2000 nits. Brightness values ​​were tested at 0V and 7V. The brightness test method was as follows: the liquid crystal was injected into the test cell, and after the UV process reaction was completed, polarizers were attached to both sides. The brightness value of the cell was tested at 0V without power and the brightness at 0V was recorded. The brightness value of the cell was tested at 7V with power and the brightness at 7V was recorded. The contrast ratio was calculated using the contrast ratio formula. Test equipment: DMS505.

[0186] A high brightness of 0V indicates poor alignment, which affects the panel's contrast.

[0187] Pretilt angle stability: Perform an 88.5° pretilt angle according to the UV1 process, and test the angle change after power aging (AC19V+DC2V). The smaller the pretilt angle change, the better. The pretilt angle change should be <0.05°.

[0188] VHR represents the voltage hold-up rate (%). The test conditions were 60±1℃, ±5V, pulse width 10ms, and voltage hold-up time 1.667ms. The test equipment was a TOYO Model 6254 LCD performance comprehensive tester.

[0189] The preparation method of the liquid crystal composition is as follows: Weigh each liquid crystal monomer according to a certain ratio and put it into a stainless steel beaker. Place the stainless steel beaker containing each liquid crystal monomer on a magnetic stirrer and heat it to melt. After most of the liquid crystal monomer in the stainless steel beaker has melted, add a magnetic rotor to the stainless steel beaker and stir the mixture evenly. After cooling to room temperature, the liquid crystal composition is obtained.

[0190] The fabrication method of the liquid crystal display device in the embodiments of the present invention is as follows: A liquid crystal composition is poured into a test cell (without a polyimide alignment layer, cell thickness 3.3 μm, ITO electrodes on the substrate surface, and no passivation layer. This alignment agent can be aligned in the planarization layer). To achieve spontaneous vertical alignment of the liquid crystal molecules, two ultraviolet irradiation processes are required: UV1 and UV2. A voltage of 15V is applied to both sides of the test cell, and an ultraviolet lamp with a main wavelength of 313nm is used for irradiation. UV1: Irradiation time is 60s, and irradiation intensity is 0.55mw / cm². 2 UV2: Irradiation time is 90 min, and irradiation intensity is 0.20 mw / cm². 2 After the ultraviolet irradiation process, a pretilt angle is formed on the inside of the test box, causing the liquid crystal molecules to spontaneously align vertically.

[0191] Brightness test method: The liquid crystal composition is poured into the test cell. After the UV process reaction is completed, polarizers are attached to both sides. The brightness value of the cell without power is recorded at 0V. The brightness value of the cell with power is recorded at 7V. The contrast ratio is calculated using the contrast ratio formula. Test equipment: DMS505.

[0192] Contrast ratio definition: Contrast ratio = Brightness value in the powered-on bright state / Brightness value in the unpowered dark state.

[0193] The liquid crystal monomer structure in the embodiments of the present invention is represented by code. The code representation methods of liquid crystal ring structure, end group and linking group are shown in Table 1 and Table 2 below.

[0194] Table 1. Corresponding codes for ring structures

[0195]

[0196] Table 2. Correspondence codes between terminal groups and linking groups

[0197]

[0198] For example:

[0199] Its code is COY-3-O2;

[0200] Its code is PP-5-3;

[0201] Its code is CY-3-O2;

[0202] Its code is CC-Cp-V1;

[0203] Its code is PGP-Cpr1-2.

[0204] The compound represented by Formula I:

[0205] The compound shown in Formula I2-1

[0206] The structural formula is as follows:

[0207] Ⅰ2-1.

[0208] Its preparation route is as follows:

[0209]

[0210] Specific preparation procedure:

[0211] Intermediate 1:

[0212] Under nitrogen protection, 1.2 mol of NaH was added to a three-necked flask, followed by the slow addition of 1.2 L of DMF. The mixture was cooled to 0 °C, and 1 mol of diethyl malonate was added dropwise. After the addition was complete, the mixture was stirred for 1 h, and then 2-benzyloxybromoethane was added dropwise. The mixture was heated to 60 °C and reacted for 3 h. After the reaction was complete, the mixture was cooled, and the reaction was quenched slowly with water. Ethyl acetate was added, and the mixture was allowed to stand and separate. The organic phase was concentrated and separated by column chromatography to give intermediate 1, a pale yellow liquid. HPLC: 92%, yield Y = 85%.

[0213] Intermediate 2:

[0214] Under nitrogen protection, 1.02 mol of NaH was added to a three-necked flask, followed by the slow addition of 1.0 L of DMF. The mixture was cooled to 0°C, and 0.85 mol of intermediate 1 was added dropwise. After the addition was complete, the mixture was stirred for 1 h, and then 3-bromopropene was added dropwise. The mixture was heated to 60°C and reacted for 3 h. After the reaction was complete, the mixture was cooled, and the reaction was quenched slowly with water. Ethyl acetate was added, and the mixture was allowed to stand and separate. The organic phase was concentrated and separated by column chromatography to obtain intermediate 2, a pale yellow liquid. HPLC: 95%, yield Y = 65%.

[0215] Intermediate 3:

[0216] Under nitrogen protection, 1.2 mol of lithium aluminum hydride was added to a three-necked flask, followed by the slow addition of 1.5 L of THF. The mixture was cooled to 0°C, and 0.5 mol of intermediate 2 was added dropwise. After the addition was complete, the mixture was stirred for 1 h. Once the reaction was complete, the mixture was cooled, and 45 g of water was slowly added, followed by 45 g of a 15 wt% sodium hydroxide solution, and then 135 g of water. The mixture was stirred for 0.5 h, filtered, and concentrated to obtain intermediate 3, a pale yellow liquid. HPLC: 90%, yield Y = 100%.

[0217] Intermediate 4:

[0218] Under nitrogen protection, 0.5 mol of intermediate 3, 1.5 mol of tert-butyldimethylchlorosilane, 1.5 mol of imidazole, and 1.5 L of THF were added to a three-necked flask and stirred overnight at room temperature. After the reaction was complete, water and ethyl acetate were added, and the mixture was extracted layer by layer, concentrated, and separated by column chromatography to obtain intermediate 4, a pale yellow liquid. HPLC: 92%, yield Y = 90%.

[0219] Intermediate 5:

[0220] Under nitrogen protection, 0.3 mol of intermediate 4 was added to a three-necked flask, followed by 1 L of DCM. The mixture was cooled to -10 °C, and boron tribromide was added dropwise. The reaction was monitored and stirred for 1 h until complete. Water and DCM were added, and the mixture was extracted layer by layer. The extract was washed with water until neutral, concentrated, and separated by column chromatography to obtain intermediate 5, a pale yellow liquid. HPLC: 93%, yield Y = 20%.

[0221] Intermediate 6:

[0222] Under nitrogen protection, 0.3 mol of pentylbiphenylboronic acid, 0.3 mol of 4-chloro-3-fluorobromobenzene, 0.4 L of water, 1.2 L of toluene, 0.12 mol of potassium carbonate, and 0.3 g of tetrakis(triphenylphosphine)palladium catalyst were added to a three-necked flask and the mixture was heated under reflux for 3 hours. After standing, the mixture was separated by column chromatography and recrystallized from toluene / ethanol to give intermediate 6, a pale yellow solid. HPLC: 98%, yield Y = 85%.

[0223] Intermediate 7:

[0224] Under nitrogen protection, 0.2 mol of intermediate 6, 0.2 mol of 4-hydroxyphenylboronic acid, 0.12 mol of potassium carbonate, 0.1 L of water, 0.3 L of toluene, and 0.3 g of catalyst tetrakis(triphenylphosphine)palladium were added to a three-necked flask. The mixture was refluxed under N2 protection for 4 hours. After the reaction was completed, the mixture was cooled, allowed to stand, separated by column chromatography, and recrystallized from toluene / ethanol to give intermediate 7 as a pale yellow solid. HPLC: 95%, yield Y = 65%.

[0225] Intermediate 8:

[0226] 0.1 mol of intermediate 7 was added to a three-necked flask. Under N2 protection, 0.4 L of DCM was added, followed by 0.25 mol of NBS. The reaction was allowed to proceed for 3 hours. After the reaction was complete, water and DCM were added to the system. The mixture was extracted by separation, dried and concentrated. The mixture was then slurried at a volume ratio of PE:EA = 10:1 and stirred for 10 min to obtain intermediate 8. The HPLC yield was 98%, and the yield Y = 76%.

[0227] Intermediate 9:

[0228] In a three-necked flask, 0.05 mol of intermediate 8, 0.055 mol of intermediate 5, 0.06 mol of triphenylphosphine, and 0.3 L of THF were added. Under N2 protection, 0.06 mol of DIAD was added dropwise at 0°C. After the addition was complete, the reaction was allowed to proceed overnight at room temperature. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted with EA, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and separated by column chromatography to obtain intermediate 9. HPLC: 98%, yield Y = 90%.

[0229] Intermediate 10:

[0230] In a 0.5 L three-necked flask, 0.05 mol of intermediate 9 and 0.3 L of THF were added. Under the protection of N2, the temperature was controlled at -80 °C, and 1.1 mol of n-butyllithium was added dropwise. After the addition was complete, the mixture was stirred at -80 °C for 1 h. Then, 1.1 mol of trimethyl borate was added dropwise, and the mixture was stirred at -80 °C for 1 h. The temperature was then allowed to rise naturally to -30 °C, quenched with water, and the mixture was separated into aqueous and organic phases. The aqueous phase was extracted with EA, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain intermediate 10. HPLC: 80%, yield Y = 80%.

[0231] Intermediate 11:

[0232] 0.05 mol of intermediate 10 and 0.3 L of THF were added to a 0.5 L three-necked flask. Under N2 protection and controlled temperature of 50 °C, 2 mol of hydrogen peroxide was added dropwise. After the addition was complete, the mixture was stirred at 60 °C for 1 h. Water was added to separate the contents, and the aqueous phase was extracted with EA. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. Intermediate 11 was obtained by column chromatography. HPLC: 93%, yield Y = 60%.

[0233] Intermediate 12:

[0234] In a three-necked flask, 0.05 mol of intermediate 11, 0.3 mol of methacrylic acid, 0.01 mol of DMAP, and 0.3 L of THF were added. Under N2 protection, 0.33 mol of DCC was added, and the mixture was stirred overnight at room temperature. The system was filtered, the filter cake was washed, the filtrate was concentrated, and column chromatography was used to separate intermediate 12. HPLC: 98%, yield Y = 90%.

[0235] Compound I2-1:

[0236] 0.03 mol of intermediate 12 and 0.2 L of THF were added to a three-necked flask. Under N2 protection, 0.06 mol of TBAF (1 mol / L) was added dropwise at 0 °C. After the addition was complete, the reaction was allowed to proceed at room temperature for 1 hour. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted twice with EA (extractant extractant), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The EA / PE system was then passed through a silica gel column and concentrated to obtain a colorless liquid compound I2-1. HPLC: 99.0%, yield Y = 65%.

[0237] The following structures can all be prepared using the method described above:

[0238] Equation I2-2, Equation I2-3, Equation I2-4.

[0239] Compounds shown in Formula I2-5

[0240] The structural formula is as follows:

[0241] Ⅰ2-5.

[0242] Its preparation route is as follows:

[0243]

[0244] Specific preparation procedure:

[0245] Intermediate 13:

[0246] 0.05 mol of intermediate 9 and 0.3 L of THF were added to a three-necked flask. Under nitrogen protection and controlled temperature of -80 °C, 1.1 mol of n-butyllithium was added dropwise. After the addition was complete, the mixture was stirred at -80 °C for 1 h. Then, 1.1 mol of DMF was added dropwise, and the mixture was stirred at -80 °C for 1 h. The temperature was then allowed to rise naturally to -30 °C, quenched with water, and the mixture was separated into aqueous and organic phases. The aqueous phase was extracted with EA, and the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain intermediate 13. HPLC: 88%, yield Y = 70%.

[0247] Intermediate 14:

[0248] In a three-necked flask, add 0.05 mol of intermediate 13, 0.3 L of THF, and 0.1 L of water. Slowly add 0.05 mol of potassium borohydride. After the addition is complete, stir at room temperature for 1 h. Add water to separate the contents into two phases. Extract the aqueous phase with EA. Combine the organic phases, wash once with saturated brine, dry to anhydrous sodium sulfate, filter, concentrate the filtrate, and separate by column chromatography to obtain intermediate 14. HPLC: 96%, yield Y = 80%.

[0249] Intermediate 15:

[0250] In a three-necked flask, 0.05 mol of intermediate 14, 0.3 mol of methacrylic acid, 0.01 mol of DMAP, and 0.3 L of THF were added. Under N2 protection, 0.33 mol of DCC was added, and the mixture was stirred overnight at room temperature. The system was filtered, the filter cake was washed, the filtrate was concentrated, and column chromatography was used to separate intermediate 15. HPLC: 97%, yield Y = 83%.

[0251] Compound I2-5:

[0252] 0.03 mol of intermediate 15 and 0.2 L of THF were added to a three-necked flask. Under N2 protection, 0.06 mol of TBAF (1 mol / L) was added dropwise at 0 °C. After the addition was complete, the reaction was allowed to proceed at room temperature for 1 hour. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted twice with EA (extractant extractant), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The EA / PE system was then passed through a silica gel column and concentrated to obtain a colorless liquid compound I2-5. HPLC: 99.0%, yield Y = 45%.

[0253] The following structures can all be prepared using the method described above:

[0254] Equation I2-6, Equation I2-7, Equation I2-8.

[0255] Compounds shown in Formula I2-15

[0256] The structural formula is as follows:

[0257] Ⅰ2-15.

[0258] Its preparation route is as follows:

[0259]

[0260] Specific preparation procedure:

[0261] Intermediate 30:

[0262] Under nitrogen protection, 0.3 mol of pentylbiphenylboronic acid, 0.3 mol of 4-chloro-3-ethylbromobenzene, 0.4 L of water, 1.2 L of toluene, 0.12 mol of potassium carbonate, and 0.3 g of tetrakis(triphenylphosphine)palladium catalyst were added to a three-necked flask and the mixture was heated under reflux for 3 hours. After standing and separation, the mixture was separated by column chromatography and recrystallized from toluene / ethanol to give intermediate 30, a pale yellow solid. HPLC: 98%, yield Y = 73%.

[0263] Intermediate 31:

[0264] Under nitrogen protection, 0.2 mol of intermediate 30, 0.2 mol of 4-hydroxyphenylboronic acid, 0.12 mol of potassium carbonate, 0.1 L of water, 0.3 L of toluene, and 0.3 g of catalyst tetrakis(triphenylphosphine)palladium were added to a three-necked flask. The mixture was refluxed under N2 protection for 4 hours. After the reaction was completed, the mixture was cooled, allowed to stand, separated by column chromatography, and recrystallized from toluene / ethanol to give intermediate 31 as a pale yellow solid. HPLC: 95%, yield Y = 45%.

[0265] Intermediate 16:

[0266] 0.1 mol of intermediate 31 was added to a three-necked flask under N2 protection, DMF was added, followed by 0.25 mol of NIS, and the reaction was allowed to proceed for 3 hours. After the reaction was complete, the system was poured into water and stirred, and a solid precipitated. The solid was filtered and separated by solid column chromatography to obtain intermediate 16. HPLC: 97%, yield Y = 86%.

[0267] Intermediate 17:

[0268] 0.08 mol of intermediate 16 was dissolved in DMF and added to a three-necked flask. 0.2 mol of tert-butyl acrylate, 0.01 mol of tetraphenylphosphine palladium, and 0.02 mol of triphenylphosphine were added. The mixture was reacted under N2 protection at 100 °C for 8 hours. After the reaction was complete, the mixture was filtered through diatomaceous earth. The filtrate was concentrated and separated by column chromatography to obtain intermediate 17. HPLC: 94%, yield Y = 30%.

[0269] Intermediate 18:

[0270] 0.08 mol of intermediate 17 was added to a three-necked flask, followed by 5 g of palladium on carbon. The mixture was purged three times with N2 and three times with hydrogen, and reacted at 50 °C for 6 hours. After the reaction was complete, the mixture was filtered through diatomaceous earth, the filtrate was concentrated, and separated by column chromatography to obtain intermediate 18. HPLC: 95%, yield Y = 87%.

[0271] Intermediate 19:

[0272] In a three-necked flask, 0.05 mol of intermediate 18, 0.055 mol of intermediate 5, 0.06 mol of triphenylphosphine, and 0.3 L of THF were added. Under N2 protection, 0.06 mol of DIAD was added dropwise at 0°C. After the addition was complete, the reaction was allowed to proceed overnight at room temperature. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted with EA, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and separated by column chromatography to obtain intermediate 19. HPLC: 98%, yield Y = 83%.

[0273] Intermediate 20:

[0274] Under nitrogen protection, 0.1 mol of lithium aluminum hydride was added to a three-necked flask, followed by the slow addition of 0.3 L of THF. The mixture was cooled to 0°C, and 0.04 mol of intermediate 19 was added dropwise. After the addition was complete, the mixture was stirred for 1 h. Once the reaction was complete, the mixture was cooled, and 4 g of water was slowly added, followed by 4 g of a 15 wt% sodium hydroxide solution, and then 12 g of water. The mixture was stirred for 0.5 h, filtered, and concentrated to obtain intermediate 20 as a pale yellow liquid. HPLC: 90%, yield Y = 100%.

[0275] Intermediate 21:

[0276] In a three-necked flask, 0.04 mol of intermediate 20, 0.12 mol of methacrylic acid, 0.01 mol of DMAP, and 0.2 L of THF were added. Under N2 protection, 0.12 mol of DCC was added, and the mixture was stirred overnight at room temperature. The system was filtered, the filter cake was washed, the filtrate was concentrated, and column chromatography was used to separate intermediate 21. HPLC: 98%, yield Y = 85%.

[0277] Compound I2-15:

[0278] 0.03 mol of intermediate 21 and 0.2 L of THF were added to a three-necked flask. Under N2 protection, 0.06 mol of TBAF (1 mol / L) was added dropwise at 0 °C. After the addition was complete, the reaction was allowed to proceed at room temperature for 1 hour. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted twice with EA (extractant extractant), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The EA / PE system was then passed through a silica gel column and concentrated to obtain a colorless liquid compound I2-15. HPLC: 99.0%, yield Y = 68%.

[0279] The mass spectrum of the compound shown in Formula I2-15 above is as follows: Figure 1 As shown.

[0280] Compounds with other structures can be prepared using the above method:

[0281] Formula I1-1, Formula I1-2, Formula I1-3, Formula I1-4, Formula I2-13, Formula I2-14, Formula I2-16, Formula I3-11, Formula I3-12, Formula I3-13, Formula I3-14, Formula I3-15, Formula I3-16, Formula I4-13, Formula I4-14, Formula I4-15, Formula I4-16, Formula I5-1, Formula I5-2, Formula I5-3, Formula I5-4, Formula I6-1, Formula I6-2, Formula I7-1, Formula I7-2, Formula I8-1, Formula I8-2.

[0282] The compound shown in Formula I 10-1

[0283] The structural formula is as follows:

[0284] Ⅰ10-1.

[0285] Its preparation route is as follows:

[0286]

[0287] Specific preparation procedure:

[0288] Intermediate 22:

[0289] Under nitrogen protection, 0.3 mol of [agent name] was added to a three-necked flask. 0.3 mol of 4-chloro-3-fluorobromobenzene, 0.4 L of water, 1.2 L of toluene, 0.12 mol of potassium carbonate, and 0.3 g of tetrakis(triphenylphosphine)palladium catalyst were added and refluxed for 3 hours. The mixture was allowed to stand, separated by column chromatography, and recrystallized from toluene / ethanol to give intermediate 22, a pale yellow solid. HPLC: 96%, yield Y = 73%.

[0290] Intermediate 23:

[0291] Under nitrogen protection, 0.2 mol of intermediate 22, 0.2 mol of 4-hydroxyphenylboronic acid, 0.12 mol of potassium carbonate, 0.1 L of water, 0.3 L of toluene, and 0.3 g of catalyst tetrakis(triphenylphosphine)palladium were added to a three-necked flask. The mixture was refluxed under N2 protection for 4 hours. After the reaction was completed, the mixture was cooled, allowed to stand, separated by column chromatography, and recrystallized from toluene / ethanol to give intermediate 23 as a pale yellow solid. HPLC: 95%, yield Y = 65%.

[0292] Intermediate 24:

[0293] 0.1 mol of intermediate 23 was added to a three-necked flask under N2 protection. DMF was added, followed by 0.25 mol of NiS, and the reaction was allowed to proceed for 3 hours. After the reaction was complete, the system was poured into water and stirred, and a solid precipitated. The solid was filtered and separated by solid-state column chromatography to obtain intermediate 24. HPLC: 94%, yield Y = 76%.

[0294] Intermediate 25:

[0295] 0.08 mol of intermediate 24 was dissolved in DMF and added to a three-necked flask. 0.2 mol of tert-butyl acrylate, 0.01 mol of tetra-triphenylphosphine palladium and 0.02 mol of triphenylphosphine were added. The mixture was protected with N2 and reacted at 100 °C for 8 hours. After the reaction was completed, the mixture was filtered through diatomaceous earth. The filtrate was concentrated and separated by column chromatography to obtain intermediate 25. HPLC: 93%, yield Y = 38%.

[0296] Intermediate 26:

[0297] 0.08 mol of intermediate 25 was added to a three-necked flask, followed by 5 g of palladium on carbon. The mixture was purged three times with N2 and three times with hydrogen, and reacted at 50 °C for 6 hours. After the reaction was completed, the mixture was filtered through diatomaceous earth, the filtrate was concentrated, and the residue was separated by column chromatography to obtain intermediate 26. The HPLC yield was 96%, and the yield Y was 79%.

[0298] Intermediate 27:

[0299] In a three-necked flask, 0.05 mol of intermediate 26, 0.055 mol of intermediate 5, 0.06 mol of triphenylphosphine, and 0.3 L of THF were added. Under N2 protection, 0.06 mol of DIAD was added dropwise at 0°C. After the addition was complete, the reaction was allowed to proceed overnight at room temperature. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted with EA, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and separated by column chromatography to obtain intermediate 27. HPLC: 95%, yield Y = 68%.

[0300] Intermediate 28:

[0301] Under nitrogen protection, 0.1 mol of lithium aluminum hydride was added to a three-necked flask, followed by the slow addition of 0.3 L of THF. The mixture was cooled to 0°C, and 0.04 mol of intermediate 27 was added dropwise. After the addition was complete, the mixture was stirred for 1 h. Once the reaction was complete, the mixture was cooled, and 4 g of water was slowly added, followed by 4 g of a 15 wt% sodium hydroxide solution, and then 12 g of water. The mixture was stirred for 0.5 h, filtered, and concentrated to obtain intermediate 28 as a pale yellow liquid. HPLC: 90%, yield Y = 98%.

[0302] Intermediate 29:

[0303] In a three-necked flask, 0.04 mol of intermediate 28, 0.12 mol of methacrylic acid, 0.01 mol of DMAP, and 0.2 L of THF were added. Under N2 protection, 0.12 mol of DCC was added, and the mixture was stirred overnight at room temperature. The system was filtered, the filter cake was washed, the filtrate was concentrated, and column chromatography was used to separate intermediate 29. HPLC: 97%, yield Y = 78%.

[0304] Compound I 10⁻¹:

[0305] 0.03 mol of intermediate 29 and 0.2 L of THF were added to a three-necked flask. Under N2 protection, 0.06 mol of TBAF (1 mol / L) was added dropwise at 0 °C. After the addition was complete, the reaction was allowed to proceed at room temperature for 1 hour. After the reaction was complete, water was added to separate the phases. The aqueous phase was extracted twice with EA (extractant extractant), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The EA / PE system was then passed through a silica gel column and concentrated to obtain a colorless liquid compound I10⁻¹. HPLC: 99.3%, yield Y = 58%.

[0306] replace for The compound shown in Formula I11-1 can be obtained by the above synthesis method.

[0307] Compare with compound D1:

[0308] D1

[0309] Liquid crystal composition:

[0310] Composition C1:

[0311] The formulation and physical properties of composition C1 are shown in Table 3 below.

[0312] Table 3 Formulation and Physical Properties of Composition C1

[0313]

[0314] Composition C2:

[0315] The formulation and physical properties of composition C2 are shown in Table 4 below.

[0316] Table 4 Formulation and physical properties of composition C2

[0317]

[0318] Composition C3:

[0319] The formulation and physical properties of composition C3 are shown in Table 5 below.

[0320] Table 5. Formulation and physical properties of composition C3

[0321]

[0322] Composition C4:

[0323] The formulation and physical properties of composition C4 are shown in Table 6 below.

[0324] Table 6. Formulation and physical properties of composition C4

[0325]

[0326] Composition C5:

[0327] The formulation and physical properties of composition C5 are shown in Table 7 below.

[0328] Table 7 Formulation and physical properties of composition C5

[0329]

[0330] Example 1

[0331] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I1-1 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0332] Example 2

[0333] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I2-13 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0334] Example 3

[0335] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I5-11 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0336] Example 4

[0337] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I7-1 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0338] Example 5

[0339] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I9-1 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0340] Example 6

[0341] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent, a compound of formula I10-1, to 100 parts of composition C1, according to the above-described method for preparing a liquid crystal composition.

[0342] Example 7

[0343] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I11-1 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0344] Example 8

[0345] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0346] Example 9

[0347] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of the self-aligning agent compound of formula I2-15 and 0.4 parts of RM-1 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0348] Example 10

[0349] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of the self-aligning agent compound represented by formula I2-15, 0.2 parts of RM-1, 0.1 parts of RM-4, and 0.1 parts of RM-5 to 100 parts of composition C1, according to the above-described method for preparing liquid crystal compositions.

[0350] Comparative Example 1

[0351] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent of formula D1 to 100 parts of composition C1, according to the above-described method for preparing a liquid crystal composition.

[0352] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 1 to 10 and Comparative Example 1 are shown in Table 8 below.

[0353] Table 8

[0354]

[0355] As can be seen from the data in Table 8 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0356] Example 11

[0357] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C2, according to the above-described method for preparing liquid crystal compositions.

[0358] Example 12

[0359] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent compound of formula I1-1 to 100 parts of composition C2, according to the above-described method for preparing liquid crystal compositions.

[0360] Example 13

[0361] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent compound of formula I2-13 to 100 parts of composition C2, according to the above-described method for preparing liquid crystal compositions.

[0362] Example 14

[0363] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent compound of formula I5-11 to 100 parts of composition C2, according to the above-described method for preparing liquid crystal compositions.

[0364] Example 15

[0365] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent, a compound of formula I7-1, to 100 parts of composition C2, according to the method for preparing the liquid crystal composition described above.

[0366] Example 16

[0367] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of the self-aligning agent compound represented by formula I2-15, 0.2 parts of RM-2 and 0.1 parts of RM-5 to 100 parts of composition C2, according to the above-described method for preparing liquid crystal compositions.

[0368] Comparative Example 2

[0369] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent of formula D1 to 100 parts of composition C2, according to the above-described method for preparing a liquid crystal composition.

[0370] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 11 to 16 and Comparative Example 2 are shown in Table 9 below.

[0371] Table 9

[0372]

[0373] As can be seen from the data in Table 9 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0374] Example 17

[0375] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C3, according to the above-described method for preparing liquid crystal compositions.

[0376] Example 18

[0377] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent compound of formula I1-1 to 100 parts of composition C3, according to the above-described method for preparing liquid crystal compositions.

[0378] Example 19

[0379] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent compound of formula I2-13 to 100 parts of composition C3, according to the above-described method for preparing liquid crystal compositions.

[0380] Example 20

[0381] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent compound of formula I3-3 to 100 parts of composition C3, according to the above-described method for preparing liquid crystal compositions.

[0382] Example 21

[0383] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent, a compound of formula I9-1, to 100 parts of composition C3, according to the method for preparing the liquid crystal composition described above.

[0384] Comparative Example 3

[0385] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent of formula D1 to 100 parts of composition C3, according to the above-described method for preparing a liquid crystal composition.

[0386] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 17 to 21 and Comparative Example 3 are shown in Table 10 below.

[0387] Table 10

[0388]

[0389] As can be seen from the data in Table 10 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0390] Example 22

[0391] A liquid crystal composition, by weight, is prepared by adding 1.0 part of a self-aligning agent compound of formula I2-15 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0392] Example 23

[0393] A liquid crystal composition, by weight, is prepared by adding 1.0 part of a self-aligning agent compound of formula I2-13 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0394] Example 24

[0395] A liquid crystal composition, by weight, is prepared by adding 1.0 part of a self-aligning agent compound of formula I5-11 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0396] Example 25

[0397] A liquid crystal composition, by weight, is prepared by adding 1.0 part of the self-aligning agent compound of formula I7-1 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0398] Example 26

[0399] A liquid crystal composition, by weight, is prepared by adding 1.0 part of a self-aligning agent compound of formula I9-1 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0400] Comparative Example 4

[0401] A liquid crystal composition, by weight, is prepared by adding 1.0 part of self-aligning agent D1 to 100 parts of composition C4, according to the above-described method for preparing liquid crystal compositions.

[0402] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 22 to 26 and Comparative Example 4 are shown in Table 11 below.

[0403] Table 11

[0404]

[0405] As can be seen from the data in Table 11 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0406] Example 27

[0407] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0408] Example 28

[0409] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent compound of formula I8-1 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0410] Example 29

[0411] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent, a compound of formula I8-2, to 100 parts of composition C5, according to the method for preparing the liquid crystal composition described above.

[0412] Example 30

[0413] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent compound of formula I5-11 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0414] Example 31

[0415] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent compound of formula I3-3 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0416] Comparative Example 5

[0417] A liquid crystal composition, by weight, is prepared by adding 0.6 parts of a self-aligning agent of formula D1 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0418] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 27 to 31 and Comparative Example 5 are shown in Table 12 below.

[0419] Table 12

[0420]

[0421] As can be seen from the data in Table 12 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0422] Example 32

[0423] A liquid crystal composition, by weight, is prepared by adding 0.7 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0424] Example 33

[0425] A liquid crystal composition, by weight, is prepared by adding 0.8 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0426] Example 34

[0427] A liquid crystal composition, by weight, is prepared by adding 0.9 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0428] Example 35

[0429] A liquid crystal composition, by weight, is prepared by adding 1.0 part of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0430] Example 36

[0431] A liquid crystal composition, by weight, is prepared by adding 1.1 parts of a self-aligning agent compound of formula I2-15 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0432] Comparative Example 6

[0433] A liquid crystal composition, by weight, is prepared by adding 1.1 parts of a self-aligning agent of formula D1 to 100 parts of composition C5, according to the above-described method for preparing liquid crystal compositions.

[0434] The 0V brightness, 7V brightness, contrast ratio, pretilt angle variation, and reliability (VHR) results of the liquid crystal compositions obtained in Examples 32 to 36 and Comparative Example 6 are shown in Table 13 below.

[0435] Table 13

[0436]

[0437] As can be seen from the data in Table 13 above, the technical solution of the present invention maintains high reliability while having good contrast and pretilt angle stability.

[0438] In summary, the technical solution of the present invention has a better alignment effect and stronger pretilt angle stability compared with alignment agents that only have polar groups such as -OH and -NH. At the same time, it can ensure compatibility with different materials, maintain a high VHR, and the particle size after polymerization reaction is moderate and the surface is relatively flat, so that the display panel has a higher contrast.

[0439] Obviously, the above embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the implementation of the present invention. For those skilled in the art, other variations or modifications can be made based on the above description. It is impossible to exhaustively list all the implementation methods here. All obvious variations or modifications derived from the technical solutions of the present invention are still within the protection scope of the present invention.

Claims

1. A liquid crystal compound, characterized in that, The liquid crystal compound is selected from the compound shown in Formula I. Ⅰ in, , , , Each represents independently , , , , , , , or In these groups, one or more H atoms may optionally be replaced by L; L represents -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally replaced by -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally replaced by halogens; R2 represents an alkyl group having at most 15 carbon atoms, an alkenyl group having at most 15 carbon atoms, or an alkynyl group having at most 15 carbon atoms, wherein one or more non-adjacent -CH2- atoms in these groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens; R1 indicates ; X1 and X2 each independently represent -OH; Sp1, Sp3, Sp5, Sp6, Z1, Z2, and Z3 each independently represent a single bond, an alkylene group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an ynylene group having up to 15 carbon atoms; wherein one or more non-adjacent -CH2- atoms in these groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with F or Cl; Sp2 represents an alkenyl group with 2-10 carbon atoms; Sp4 indicates a tetravalent group; a and b each represent 0 or 1 independently; P1 represents a polymerizable group.

2. The liquid crystal compound according to claim 1, characterized in that, The compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I1 to I11 below. Ⅰ1、 Ⅰ2、 Ⅰ3、 Ⅰ4、 Ⅰ5、 Ⅰ6、 Ⅰ7、 Ⅰ8、 Ⅰ9、 Ⅰ10、 Ⅰ11； in, r1, r2, r3, and r4 each independently represent 0, 1, 2, or 3; L1, L2, L3, and L4 each independently represent -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens; and at least one of L1, L2, L3, and L4 is -Sp1-P1.

3. The liquid crystal compound according to claim 2, characterized in that, The compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I1' to I11'. Ⅰ1’、 Ⅰ2’、 Ⅰ3’、 Ⅰ4’、 Ⅰ5’、 Ⅰ6’、 Ⅰ7’、 Ⅰ8’、 Ⅰ9’、 Ⅰ10’、 Ⅰ11’； Among them, at least one of L1 and L2 is -Sp1-P1.

4. A liquid crystal composition, characterized in that, It comprises one or more liquid crystal compounds as described in any one of claims 1-3.

5. The liquid crystal composition according to claim 4, characterized in that, It contains 0.1 to 2% by mass of the compound represented by Formula I.

6. The liquid crystal composition according to claim 5, characterized in that, In the liquid crystal composition shown, the compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I2, I5, and I7. Ⅰ2、 Ⅰ5、 Ⅰ7； in, r1, r2, r3, and r4 each independently represent 0, 1, 2, or 3; L1, L2, L3, and L4 each independently represent -F, -Cl, -CN, -Sp1-P1, an alkyl group having up to 15 carbon atoms, an alkenyl group having up to 15 carbon atoms, or an alkynyl group having up to 15 carbon atoms, wherein one or more non-adjacent -CH2- groups are optionally substituted with -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that -O- and / or -S- and / or -NH- are not directly connected to each other, and one or more H atoms in these groups are optionally substituted with halogens; and at least one of L1, L2, L3, and L4 is -Sp1-P1.

7. The liquid crystal composition according to claim 6, characterized in that, In the liquid crystal composition shown, the compound represented by Formula I is selected from the group consisting of compounds represented by Formulas I2', I5' and I7'. Ⅰ2’、 Ⅰ5’、 Ⅰ7’； Among them, at least one of L1 and L2 is -Sp1-P1.

8. The liquid crystal composition according to claim 5, characterized in that, The liquid crystal composition further comprises 0 to 2% polymerizable compound by weight percentage.

9. The liquid crystal composition according to claim 8, characterized in that, The liquid crystal composition contains, by weight percentage, 0.3 to 1.5% of the compound represented by Formula I and 0.1 to 1.5% of the polymerizable compound.

10. The liquid crystal composition according to claim 8 or 9, characterized in that, The polymerizable compound is selected from the group consisting of compounds represented by the following formulas RM-1 to RM-7. RM-1、 RM-2、 RM-3、 RM-4、 RM-5、 RM-6、 RM-7。 11. The liquid crystal composition according to claim 10, characterized in that, The liquid crystal composition contains at least two polymerizable compounds selected from those shown in formulas RM-1 to RM-7.

12. The liquid crystal composition according to any one of claims 4-9, characterized in that, The liquid crystal composition further comprises one or more compounds represented by Formula II. Ⅱ in, R3 and R4 each independently represent straight-chain or branched alkyl groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, or alkoxy groups with 1-10 carbon atoms; m1 represents 1, 2, or 3; , Each represents independently , , or When m1 represents 2 or 3, Each independently is the same or different; and / or The liquid crystal composition further comprises one or more compounds represented by Formula III. Ⅲ in, R5 and R6 each independently represent a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropyl, cyclobutyl, or cyclopentyl. Z represents a single bond, -CH2O-, -CH2CH2-, or -CH=CH-; m2 represents 1, 2, or 3; , Each represents independently , , , or ,and , At least one of them represents When m2 represents 2 or 3, Each independently is the same or different; and / or The liquid crystal composition further comprises one or more compounds represented by Formula IV. Ⅳ in, R7 and R8 each independently represent a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropyl, cyclobutyl, or cyclopentyl. W represents -O-, -S-, or -CH2O-.

13. The liquid crystal composition according to claim 12, characterized in that, The liquid crystal composition comprises, by weight percentage: 19-60% of the compound represented by Formula II, and / or 30-80% of the compound represented by formula III, and / or 0-15% of the compound represented by formula IV.

14. The liquid crystal composition according to claim 12, characterized in that, The compound represented by Formula II is selected from the group consisting of compounds represented by Formulas II-1 to II-8 below. Ⅱ-1、 Ⅱ-2、 Ⅱ-3、 Ⅱ-4、 Ⅱ-5、 Ⅱ-6、 Ⅱ-7、 Ⅱ-8； in, R 31 R 41 Each of these independently represents a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms; and / or The compound represented by Formula III is selected from the group consisting of compounds represented by Formulas III-1 to III-13. Ⅲ-1、 Ⅲ-2、 Ⅲ-3、 Ⅲ-4、 Ⅲ-5、 Ⅲ-6、 Ⅲ-7、 Ⅲ-8、 Ⅲ-9、 Ⅲ-10、 Ⅲ-11、 Ⅲ-12、 Ⅲ-13； in, R 51 R 61 Each of these groups independently represents a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropylene, cyclobutylene, or cyclopentylene; and / or The compound represented by Formula IV is selected from the group consisting of compounds represented by Formulas IV-1 to IV-3 below. Ⅳ-1 Ⅳ-2 Ⅳ-3 in, R 71 R 81 Each of these groups independently represents a straight-chain or branched alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more non-adjacent -CH2- groups may be substituted with cyclopropylene, cyclobutylene, or cyclopentylene.

15. The liquid crystal composition according to claim 14, characterized in that, The liquid crystal composition comprises at least one compound represented by Formula I. At least one compound represented by Formula II, and At least one compound represented by Formula III and / or Formula IV.

16. The liquid crystal composition according to claim 15, characterized in that, The liquid crystal composition contains: At least one compound represented by Formula I, At least one polymerizable compound selected from compounds represented by formulas RM-1, RM-2, RM-4, and RM-5, At least one compound represented by Formula II, and At least one compound represented by Formula III and / or Formula IV.

17. The liquid crystal composition according to claim 16, characterized in that, Based on mass percentage, it comprises: 0.4 to 1.2% of the compound represented by Formula I, 0.1 to 0.7% of the polymerizable compound, 19 to 60% of the compound represented by Formula II, 30 to 80% of the compound represented by Formula III, and 0 to 15% of the compound represented by Formula IV.

18. A liquid crystal display element or liquid crystal display, characterized in that, The liquid crystal composition comprises any one of claims 4-17, wherein, The liquid crystal display element is an active matrix display element or a passive matrix display element; or The liquid crystal display is an active matrix display or a passive matrix display.

Images