Dioxane-containing negative liquid crystal compound, and preparation method and application thereof

Abstract

This invention relates to a dioxane-containing negative liquid crystal compound, its preparation method, and its application. The compound has the structure shown in Formula I. The compound prepared by this invention has a large dielectric, a large refractive index, and a clearing point, as well as a wide phase transition temperature. Furthermore, the compound has a short synthesis route, low raw material cost, and simple post-processing, making it suitable for industrial production.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis technology, and relates to a dioxane-containing negative liquid crystal compound, its preparation method, and its application. Background Technology

[0002] Since its inception, Liquid Crystal Display (LCD) technology has occupied a crucial position in various display fields due to its numerous advantages, including thinness, low power consumption, no radiation, and ease of mass production. In LCD devices, liquid crystal material is the core component, and its performance directly determines the quality of the display. Liquid crystal molecules can change their alignment and orientation under conditions such as an applied electric field, thereby regulating the transmission and reflection of light to achieve image display.

[0003] Negative liquid crystal compounds have unique and important application value. They can play a key role in certain display modes. Compared with positive liquid crystals, negative liquid crystals also show advantages in some scenarios that require fast response. Their response speed can meet the application scenarios with high requirements for display timeliness, such as fast switching of dynamic images, which helps to reduce image ghosting and improve display smoothness.

[0004] In recent years, people have increasingly higher requirements for the performance of liquid crystal display elements, such as high contrast, display capacity and response time. Therefore, providing a liquid crystal compound that meets the above requirements and is simple to synthesize and low in cost has become an urgent problem to be solved in this field. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide a dioxane-containing negative liquid crystal compound, its preparation method, and its applications.

[0006] To achieve this objective, the present invention employs the following technical solution:

[0007] In a first aspect, the present invention provides a dioxane-containing negative liquid crystal compound having a structure as shown in Formula I:

[0008]

[0009] Wherein, G1 and G2 are each independently selected from hydrogen, C1-C12 alkyl, at least one C1-C12 alkyl group substituted with oxygen, sulfur, carbonyl, olefin or alkyne, C1-C12 alkoxy group, at least one C1-C12 alkoxy group substituted with oxygen, sulfur, carbonyl, olefin or alkyne.

[0010] Cycloaca A is selected from 1,4-cyclohexyl, cyclopentyl, cyclopentenyl, 1,4-cyclohexenyl, cyclobutyl, and glycidyl, wherein one or more hydrogen atoms in 1,4-cyclohexyl, cyclopentyl, cyclopentenyl, 1,4-cyclohexenyl, cyclobutyl, and glycidyl are substituted with fluorine, chlorine, methyl, trifluoromethyl, ethyl, or methoxy.

[0011] n is selected from 0, 1, or 2;

[0012] Y is selected from O or S;

[0013] X2 and X3 are each independently selected from hydrogen, fluorine, chlorine, methyl, or methoxy.

[0014] Preferably, the structure of the dioxane-containing negative liquid crystal compound is selected from any one of the following structures:

[0015]

[0016] Preferably, the dioxane-containing negative liquid crystal compound is selected from any one of the following:

[0017]

[0018]

[0019] In a second aspect, the present invention provides a method for preparing a dioxane-containing negative liquid crystal compound according to the first aspect, the method comprising:

[0020] (1) React the compound shown in Formula II with the compound shown in Formula III to obtain the compound shown in Formula IV;

[0021]

[0022] X1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy or methanesulfonyloxy;

[0023] (2) The compound shown in Formula IV is reacted with the compound shown in Formula V to obtain the product;

[0024]

[0025] Preferably, step (1) is carried out under the conditions of a first organic solvent and a dehydrating agent.

[0026] Preferably, the molar ratio of the compound represented by Formula II to the compound represented by Formula III is (0.8-2):1, and more preferably (0.9-1.2):1.

[0027] The specific point values ​​in (0.8-2) can be selected from 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, etc. Other specific point values ​​within the above range can also be selected, which will not be elaborated here.

[0028] Preferably, the molar ratio of the compound represented by Formula III, the first organic solvent, and the dehydrating agent is 1:(3-20):(0.05-1), and more preferably 1:(3-10):(0.05-1).

[0029] The specific point values ​​in (3-20) can be selected from 3, 5, 8, 10, 12, 15, 18, 20, etc., and the specific point values ​​in (0.05-1) can be selected from 0.05, 0.08, 0.1, 0.2, 0.5, 0.8, 1, etc. Other specific point values ​​within the above range can be selected, which will not be elaborated here.

[0030] Preferably, the molar ratio of the compound represented by Formula II, the compound represented by Formula III, the first organic solvent, and the dehydrating agent is (0.9-1.2):1:(3-10):(0.05-0.2).

[0031] The specific point values ​​in (0.9-1.2) can all be selected from 0.9, 1, 1.1, 1.2, etc.; the specific point values ​​in (3-10) can all be selected from 3, 4, 5, 6, 7, 8, 9, 10, etc.; the specific point values ​​in (0.05-0.2) can all be selected from 0.05, 0.08, 0.1, 0.12, 0.15, 0.18, 0.2, etc. Other specific point values ​​within the above range can also be selected, which will not be elaborated here.

[0032] Preferably, the reaction temperature in step (1) is 40-110℃ and the time is 0.5-24h.

[0033] Temperatures can be selected from 40℃, 50℃, 60℃, 70℃, 80℃, 90℃, 100℃, 110℃, etc., and time can be selected from 0.5h, 1h, 2h, 5h, 8h, 10h, 12h, 15h, 18h, 20h, 22h, 24h, etc. Other specific values ​​within the above range can also be selected, which will not be elaborated here.

[0034] Preferably, the first organic solvent includes any one or a combination of at least two of dichloromethane, dichloroethane, petroleum ether, n-heptane, toluene, and xylene.

[0035] Preferably, the first organic solvent includes any one or a combination of at least two of dichloromethane, petroleum ether, n-heptane, or toluene.

[0036] Preferably, the dehydrating agent comprises any one or a combination of at least two of the following: a saturated solution of p-toluenesulfonic acid, p-toluenesulfonic acid pyridinium salt, or hydrochloric acid chloride.

[0037] Preferably, the dehydrating agent comprises toluenesulfonic acid and / or p-toluenesulfonic acid pyridine salt.

[0038] Preferably, step (2) is carried out under the conditions of a second organic solvent and a catalyst.

[0039] Preferably, the molar ratio of the compound represented by Formula IV to the compound represented by Formula V is (0.9-2):1, and more preferably (0.9-1.2):1.

[0040] The specific point values ​​in (0.8-2) can be selected from 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, etc. Other specific point values ​​within the above range can also be selected, which will not be elaborated here.

[0041] Preferably, the molar ratio of the compound represented by Formula V, the second organic solvent, and the catalyst is 1:(3-20):(0.05-1), and more preferably 1:(3-10):(0.05-0.5).

[0042] The specific point values ​​in (3-20) can be selected from 3, 5, 8, 10, 12, 15, 18, 20, etc., and the specific point values ​​in (0.05-1) can be selected from 0.05, 0.08, 0.1, 0.2, 0.5, 0.8, 1, etc. Other specific point values ​​within the above range can be selected, which will not be elaborated here.

[0043] Preferably, the molar ratio of the compound represented by Formula IV, the compound represented by Formula V, the second organic solvent, and the catalyst is (0.9-1.2):1:(3-10):(0.05-0.5).

[0044] The specific point values ​​in (0.9-1.2) can all be selected from 0.9, 1, 1.1, 1.2, etc.; the specific point values ​​in (3-10) can all be selected from 3, 4, 5, 6, 7, 8, 9, 10, etc.; the specific point values ​​in (0.05-0.5) can all be selected from 0.05, 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, etc. Other specific point values ​​within the above range can also be selected, which will not be elaborated here.

[0045] Preferably, step (2) is carried out under alkaline conditions.

[0046] Preferably, the alkali includes any one or a combination of at least two of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, and potassium tert-butoxide.

[0047] Preferably, the temperature in step (2) is 40-130℃ and the time is 0.5-24h.

[0048] Temperatures can be selected from 40℃, 50℃, 60℃, 70℃, 80℃, 90℃, 100℃, 110℃, 120℃, 130℃, etc., and time can be selected from 0.5h, 1h, 2h, 5h, 8h, 10h, 12h, 15h, 18h, 20h, 22h, 24h, etc. Other specific values ​​within the above ranges can also be selected, which will not be elaborated here.

[0049] Preferably, the second organic solvent includes any one or a combination of at least two of toluene, n-heptane, acetonitrile, tetrahydrofuran, dimethylformamide, and dimethylacetamide.

[0050] Preferably, the catalyst comprises any one or a combination of at least two of sodium iodide, potassium iodide, tetrabutylammonium bromide, and 18-crown-6-ether.

[0051] Thirdly, the present invention provides a liquid crystal composition comprising the dioxane-containing negative liquid crystal compound described in the first aspect.

[0052] The negative liquid crystal compound containing dioxane accounts for 0.1%-30% of the weight of the liquid crystal composition, for example, 0.1%, 0.5%, 1%, 5%, 10%, 20%, 25% or 30%.

[0053] Preferably, the liquid crystal composition of the present invention further comprises: one or more compounds of general formula M:

[0054] Preferably, the liquid crystal composition further includes at least one compound of general formula M, at least one compound of general formula A1, and at least one compound of general formula A2.

[0055]

[0056] R M1 and R M2 Each can independently represent -H, a straight-chain or branched alkyl group containing 1-12 carbon atoms, One or more non-adjacent -CH2- atoms in the straight-chain or branched alkyl group containing 1-12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-.

[0057] R A1 and R A2 Each independently represents a straight-chain or branched alkyl group containing 1-12 carbon atoms. One or more non-adjacent -CH2- atoms in the straight-chain or branched alkyl group containing 1-12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-, and the straight-chain or branched alkyl group containing 1-12 carbon atoms... One or at least two -H can be independently replaced by -F or -Cl;

[0058] Z M1 and Z M2 Each can independently represent a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, or -(CH2)4-;

[0059] Z A11 Z A21 and Z A22 Each can independently represent a single bond, -CH2CH2-, -CF2CF2-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -CF=CF-, -CH2O-, or -OCH2-;

[0060] L A11 L A12 L A13 L A21 and L A22 Each can independently represent -H, an alkyl group containing 1-3 carbon atoms, or a halogen;

[0061] X A1 and X A2 Each can independently represent a halogen, a haloalkyl or haloalkoxy group containing 1-5 carbon atoms, or a haloalkenyl or haloalkenoxy group containing 2-5 carbon atoms.

[0062] ring ring and ring Each represents independently in, One or at least two of the -CH2- can be replaced by -O-. At most one -H in the halogen can be replaced by a halogen;

[0063] ring ring ring and ring Each represents independently in, One or more of the -CH2- bonds can be replaced by -O- bonds, and one or more single bonds in a ring can be replaced by double bonds. One or more of the -H can be replaced by -CN, -F or -Cl, and -CH= in one or more of the rings can be replaced by -N=;

[0064] n M1 n A11 and n A2 Each can independently represent 0, 1, 2, or 3, and when n M1 When = 2 or 3, the ring They can be the same or different, Z M2 They can be the same or different; when n A11 When = 2 or 3, the ring They can be the same or different, ZA11 can be the same or different; when n A2 When = 2 or 3, the ring They can be the same or different, Z A21 They can be the same or different;

[0065] n A12 Represents 1 or 2, and when n A12 When = 2, ring They can be the same or different.

[0066] In some embodiments of the present invention, the compound of general formula M is selected from the following compounds:

[0067]

[0068]

[0069]

[0070] Preferably, the compound of general formula M accounts for 0.1%-90% of the weight percentage of the liquid crystal composition, for example, 0.1%, 0.5%, 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, or 90%.

[0071] The content of compounds of general formula M must be appropriately adjusted according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drip marks, burn-in, and dielectric anisotropy.

[0072] Regarding the weight percentage of the compound of general formula M in the liquid crystal composition of the present invention, the preferred lower limit is 0.1%, 1%, 10%, 20%, 30%, 40%, or 50% relative to the total weight of the liquid crystal composition of the present invention; the preferred upper limit is 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 35%, or 25% relative to the total weight of the liquid crystal composition of the present invention.

[0073] Regarding the content of compounds of general formula M, when it is necessary to maintain a low viscosity and a short response time in the liquid crystal composition of the present invention, it is preferable to have a higher lower limit and a higher upper limit; further, when it is necessary to maintain a high clearing point and good temperature stability in the liquid crystal composition of the present invention, it is preferable to have a higher lower limit and a higher upper limit; in order to keep the driving voltage low and increase the absolute value of dielectric anisotropy, it is preferable to have a lower lower limit and a lower upper limit.

[0074] In some embodiments of the present invention, when reliability is of priority, it is preferred that RM1 and RM2 are both alkyl; when reducing the volatility of the compound is of priority, it is preferred that RM1 and RM2 are both alkoxy; when reducing viscosity is of priority, it is preferred that at least one of RM1 and RM2 is alkenyl.

[0075] In some embodiments of the invention, the compound of general formula M is preferably free from the group consisting of compounds of general formulas M1, M2, M3, M4, M5, M7, M8, M9, M10, M11, M13, M15, M16, M17, M18, M19, M20, M21, M22, M23 and M24.

[0076] In some embodiments of the invention, compounds of general formula M are further preferably the group consisting of compounds of general formulas M1, M2, M4, M5, M9, M11, M13, M20 and M22.

[0077] In some embodiments of the present invention, in compounds of general formula M1, RM1 represents a straight-chain or branched alkyl or alkoxy group containing 1 to 7 carbon atoms; more preferably, a straight-chain or branched alkyl or alkoxy group containing 1 to 5 carbon atoms.

[0078] Preferred weight percentages of the compound of general formula M1 in the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of general formula M1 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, or 30%; the preferred upper limit of the weight percentage of the compound of general formula M1 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, or 10%.

[0079] To particularly improve the response time of the liquid crystal composition of the present invention, it is preferred that the compound of general formula M1 has RM1 as ethyl, n-propyl, butyl, or pentyl and RM2 as methyl or methoxy, the compound of general formula M1 has RM1 as ethyl, n-propyl, butyl, or pentyl and RM2 as ethyl or ethoxy, or the compound of general formula M1 has RM1 as n-propyl, butyl, or pentyl and RM2 as n-propyl or propoxy.

[0080] The preferred lower limit of the weight percentage of the compound of general formula M1 in which RM1 is n-propyl and RM2 is ethyl relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18% or 20%; the preferred upper limit of the weight percentage of the compound of general formula M1 in which RM1 is n-propyl and RM2 is ethyl relative to the total weight of the liquid crystal composition of the present invention is 20%, 17%, 15%, 13%, 10%, 8%, 7% or 6%.

[0081] The preferred weight percentage of the compound of general formula M2 in the liquid crystal composition of the present invention is as follows: the lower limit of the weight percentage of the compound of general formula M2 in the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7% or 10% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the weight percentage of the compound of general formula M2 in the liquid crystal composition of the present invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the present invention.

[0082] The preferred weight percentage of the compound of general formula M4 in the liquid crystal composition of the present invention is as follows: the lower limit of the weight percentage of the compound of general formula M4 in the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7% or 10% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the weight percentage of the compound of general formula M4 in the liquid crystal composition of the present invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the present invention.

[0083] Regarding the preferred weight percentage of the compound of general formula M9 in the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of general formula M9 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, or 40%; the preferred upper limit of the weight percentage of the compound of general formula M9 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 50%, 40%, 35%, 30%, 20%, 15%, 10%, or 5%.

[0084] In some embodiments of the present invention, depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence, it is preferable to use compounds containing the general formula M9 in which RM1 is a straight-chain or branched alkenyl group containing 2-4 carbon atoms and RM2 is CH3-. The straight-chain or branched alkenyl group containing 2-4 carbon atoms is further preferably...

[0085] Relative to the total weight of the liquid crystal composition of the present invention, RM1 in the compound of general formula M9 is The preferred lower limit of the weight percentage of the compound RM2 being CH3- in the liquid crystal composition of the present invention is 1%, 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, or 21%, and the preferred upper limit is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, or 8%. When both compounds are present, the preferred lower limit of the weight percentage of the two compounds relative to the total weight of the liquid crystal composition of the present invention is 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24%, or 30%, and the preferred upper limit is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, or 9%.

[0086] The preferred weight percentage of the compound of general formula M10 in the liquid crystal composition of the present invention is as follows: the lower limit of the weight percentage of the compound of general formula M10 in the liquid crystal composition of the present invention is 1%, 2%, 3%, 4%, 5%, 7%, 10%, 14%, 16% or 20% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the weight percentage of the compound of general formula M10 in the liquid crystal composition of the present invention is 45%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the present invention.

[0087] In some embodiments of the present invention, depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence, it is preferable to use compounds containing the general formula M10 in which RM1 is a straight-chain or branched alkenyl group containing 2-4 carbon atoms and RM2 is CH3-. The straight-chain or branched alkenyl group containing 2-4 carbon atoms is further preferably...

[0088] Relative to the total weight of the liquid crystal composition of the present invention, RM1 in the compound of general formula M10 is The preferred lower limit of the weight percentage of the compound RM2 being CH3- in the liquid crystal composition of the present invention is 1%, 3%, 4%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, or 20%, and the preferred upper limit is 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, or 8%. When both compounds are present, the preferred lower limit of the weight percentage of the two compounds in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24%, or 30%, and the preferred upper limit is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, or 13%.

[0089] Regarding the preferred weight percentage of the compound of general formula M11 in the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of general formula M11 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, or 40%; the preferred upper limit of the weight percentage of the compound of general formula M11 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 50%, 40%, 35%, 30%, 20%, 15%, 10%, or 5%.

[0090] In some embodiments of the present invention, the compound of general formula M11 is preferably a compound in which RM1 is n-propyl or n-pentyl and RM2 is C2H5-, or preferably RM1 is... The compound in which RM2 is n-propyl, or preferably RM1 is n-propyl, n-butyl or n-pentyl and RM2 is CH3O-; particularly preferred are compounds in which RM1 is n-propyl and RM2 is C2H5-.

[0091] Regarding the preferred weight percentage of the compound of general formula M13 in the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of general formula M13 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, or 40%; the preferred upper limit of the weight percentage of the compound of general formula M13 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 50%, 40%, 35%, 30%, 20%, 15%, 10%, or 5%.

[0092] In some embodiments of the present invention, compounds of general formula M13 preferably have RM1 and RM2 each independently representing straight-chain or branched alkyl compounds containing 2-5 carbon atoms, or preferably one of RM1 and RM2 is... The other is a compound of CH3- or C2H5-.

[0093] Regarding the preferred weight percentage of the compound of general formula M15 in the liquid crystal composition of the present invention: the preferred lower limit value of the weight percentage of the compound of general formula M15 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35%, or 40%; the preferred upper limit value of the weight percentage of the compound of general formula M15 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8%, or 5%.

[0094] Regarding the preferred weight percentage of the compound of general formula M16 in the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of general formula M16 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35%, or 40%; the preferred upper limit of the weight percentage of the compound of general formula M16 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8%, or 5%.

[0095] Regarding the weight percentage of compounds of general formulas M20 to M24 in the liquid crystal composition of the present invention, the preferred lower limit values ​​are 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, or 20% relative to the total weight of the liquid crystal composition of the present invention; and the preferred upper limit values ​​are 30%, 25%, 23%, 20%, 18%, 15%, 12%, 10%, or 5% relative to the total weight of the liquid crystal composition of the present invention.

[0096] In some embodiments of the present invention, the compound of general formula A-1 is selected from the following compounds:

[0097]

[0098]

[0099]

[0100]

[0101] Wherein, RA1 represents a straight-chain or branched alkyl group containing 1-8 carbon atoms. One or more non-adjacent -CH2- groups in the straight-chain or branched alkyl groups containing 1-8 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or at least two -H groups present in these groups may be independently replaced by -F or -Cl.

[0102] Rv and Rw each independently represent -CH2- or -O-;

[0103] LA11, LA12, LA11', LA12', LA14, LA15, and LA16 each independently represent -H or -F;

[0104] LA13 and LA13' each independently represent -H or -CH3;

[0105] XA1 represents -F, -CF3, or -OCF3; and v and w each independently represent 0 or 1.

[0106] In some embodiments of the present invention, the compound of general formula A-1 accounts for 0.1%-80% by weight of the liquid crystal composition, for example 0.1%, 0.5%, 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75% or 80%.

[0107] Regarding the preferred weight percentage of the compound of general formula A-1 in the liquid crystal composition of the present invention: the preferred lower limit value of the weight percentage of the compound of general formula A-1 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 15%, 17%, 18% or 20%; the preferred upper limit value of the weight percentage of the compound of general formula A-1 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% or 25%.

[0108] Regarding the preferred content of the compound of general formula A-1, in order to keep the viscosity of the liquid crystal composition of the present invention low and the response speed fast, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; furthermore, in order to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability good, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; in addition, in order to keep the driving voltage low and to increase the absolute value of dielectric anisotropy, it is preferable to keep the lower limit value slightly high and the upper limit value slightly high.

[0109] In some embodiments of the present invention, the compound of general formula A-1 is preferably selected from the group consisting of compounds of general formula A-1-1, general formula A-1-4, general formula A-1-7, general formula A-1-13, general formula A-1-14, general formula A-1-15, general formula A-1-16 and general formula A-1-17.

[0110] In some embodiments of the invention, the compound of general formula A-1 is further preferably the group consisting of compounds of general formulas A-1-4, A-1-7, A-1-13, A-1-14 and A-1-15.

[0111] Preferably, the compound of general formula A-2 is selected from the following compounds:

[0112]

[0113]

[0114]

[0115] Wherein, RA2 represents a straight-chain or branched alkyl group containing 1-8 carbon atoms, wherein one or more non-adjacent -CH2- groups of the straight-chain or branched alkyl group containing 1-8 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or at least two -H groups present in these groups can be independently replaced by -F or -Cl;

[0116] LA21, LA22, LA23, LA24, and LA25 each independently represent -H or -F; and

[0117] XA2 represents -F, -CF3, -OCF3, or -CH2CH2CH=CF2.

[0118] In some embodiments of the present invention, the compound of general formula A-2 accounts for 0.1%-80% by weight of the liquid crystal composition, for example, 0.1%, 0.5%, 1%, 5%, 10%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, or 80%.

[0119] Regarding the preferred weight percentage of the compound of general formula A-2 in the liquid crystal composition of the present invention: the preferred lower limit value of the weight percentage of the compound of general formula A-2 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 15%, 17%, 18% or 20%; the preferred upper limit value of the weight percentage of the compound of general formula A-2 in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% or 25%.

[0120] Regarding the preferred content of the compound of general formula A-2, in order to keep the viscosity of the liquid crystal composition of the present invention low and the response speed fast, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; furthermore, in order to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability good, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; in addition, in order to keep the driving voltage low and to increase the absolute value of dielectric anisotropy, it is preferable to keep the lower limit value slightly high and the upper limit value slightly high.

[0121] In some embodiments of the present invention, the compound of general formula A-2 is preferably selected from the group consisting of compounds of general formula A-2-4, general formula A-2-8, general formula A-2-11 and general formula A-2-12.

[0122] In addition to the compounds described above, the liquid crystal compositions of the present invention also include any one or a combination of at least two of the following: nematic liquid crystals, smectic liquid crystals, cholesterol liquid crystals, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers, or light stabilizers.

[0123] Preferably, the dopants in the liquid crystal composition include:

[0124]

[0125]

[0126] Preferably, the dopant accounts for 0-5% of the weight percentage of the liquid crystal composition, for example, 0%, 0.1%, 0.5%, 1%, 2%, 3%, 4% or 5%; more preferably 0-1%.

[0127] Preferably, the antioxidants and light stabilizers used in the liquid crystal composition of the present invention are the following substances:

[0128]

[0129]

[0130]

[0131] Where n represents a positive integer from 1 to 12.

[0132] Preferably, the light stabilizer is selected from the light stabilizers shown below:

[0133]

[0134]

[0135] Preferably, the light stabilizer accounts for 0-5% of the total weight of the liquid crystal composition, for example, 0%, 0.1%, 0.5%, 1%, 2%, 3%, 4% or 5%; more preferably, the light stabilizer accounts for 0-1% of the total weight of the liquid crystal composition; particularly preferably, the light stabilizer accounts for 0.01-0.1% of the total weight of the liquid crystal composition.

[0136] Fourthly, the present invention provides the use of the terminal alkene dioxane-containing liquid crystal compound according to the first aspect or the liquid crystal composition according to the third aspect in the preparation of a liquid crystal display device.

[0137] Compared with the prior art, the present invention has the following beneficial effects:

[0138] 1. Compounds of the general formula P have a large dielectric, a large refractive index and a clearing point, and a wide phase transition temperature.

[0139] 2. The synthesis route is short, the raw material cost is low, and the post-processing is simple, making it suitable for industrial production. Detailed Implementation

[0140] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0141] Example 1

[0142] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0143]

[0144] (1) In a 250 mL three-necked flask, 14.18 g (120 mmol) of compound A-1, 19.62 g (100 mmol, 40% aqueous solution) of B-1, and 1.9 g (10 mmol) of p-toluenesulfonic acid were added to 100 mL of toluene. A water separation apparatus was set up, and the mixture was heated to 110 °C and refluxed for 3 h to separate water. After cooling to room temperature, 150 mL of water was added to the reaction solution to separate the aqueous phase. The aqueous phase was extracted with 2 × 100 mL of toluene, and the organic phases were combined. The mixture was washed with 3 × 80 mL of water, and the solvent was evaporated at 80 °C under negative pressure to obtain 15.4 g of light yellow oily liquid C-1.

[0145] The purity of compound C-1 was 96.3% (including cis and trans), and the yield was 86.2%.

[0146] (2) 15.4 g (86.2 mmol) of compound C-1, 24.67 g (80 mmol) of compound D-1, 31.28 g (96 mmol) of cesium carbonate and 1.33 g (8 mmol) of potassium iodide were added to a 250 mL three-necked flask containing 100 mL of dimethylformamide and reacted at 110 °C for 2 h.

[0147] (3) Post-treatment: Cool to room temperature, add 300 mL of water, stir, filter, and slurry the filter cake three times with 3 x 100 mL of water and once with 100 mL of ethanol. Filter and dry. Spread 15 g of 200-300 mesh silica gel, concentrate the product, dissolve it in petroleum ether, pass it through a column, evaporate the solvent at 50 °C to obtain 28 g of white solid. Add toluene:ethanol = 2:4, recrystallize, freeze at -30 °C for 3 h, filter through a Buchner funnel, and dry to obtain 26.67 g of white solid.

[0148] Compound P-1 purity: 99.94%; yield: 74%.

[0149] The target product was characterized by mass spectrometry (MS), M+(450): 41(10%), 55(28%), 83(37%), 129(100%), 251(23%), 252(9%), 450(31%), 451(9%).

[0150] Example 2

[0151] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0152]

[0153] (1) In a 250 mL three-necked flask, 14.18 g (120 mmol) of compound A-1, 19.62 g (100 mmol, 40% aqueous solution) of B-1, and 2.5 g (10 mmol) of p-toluenesulfonic acid pyridine salt were added to 100 mL of dichloromethane. A water separation apparatus was set up, and the mixture was heated to 40 °C and refluxed for 0.5 h to separate the water. After cooling to room temperature, 150 mL of water was added for lysis. The aqueous phase was extracted with 2 × 100 mL of dichloromethane, and the organic phases were combined. The mixture was washed with 3 × 80 mL of water, and the solvent was concentrated and evaporated at 40 °C to obtain 15.7 g of light yellow oily liquid C-1.

[0154] Compound C-1 has a purity of 97.8% (including cis and trans) and a yield of 87.9%.

[0155] (2) 15.7g (87.9mmol) of compound C-1, 24.67g (80mmol) of compound D-1, 13.25g (96mmol) of potassium carbonate and 2.58g (8mmol) of tetrabutylammonium bromide were added to a 250mL three-necked flask containing 100mL of dimethylformamide and reacted at 110℃ for 2h.

[0156] (3) Post-treatment: Cool to room temperature, add 300 mL of water, stir, filter, and slurry the filter cake three times with 3 × 100 mL of water and once with 100 mL of ethanol. Filter and dry. Spread 15 g of 200-300 mesh silica gel, concentrate the product, dissolve it in petroleum ether, pass it through a column, evaporate the solvent at 50 °C to obtain 28 g of white solid. Add toluene:ethanol = 2:4, recrystallize, freeze at -30 °C for 3 h, filter through a Buchner funnel, and dry to obtain 26.67 g of white solid.

[0157] Compound P-1 purity: 99.94%; yield: 74%.

[0158] The target product was characterized by mass spectrometry (MS), M+(450): 41(10%), 55(28%), 83(37%), 129(100%), 251(23%), 252(9%), 450(31%), 451(9%).

[0159] Example 3

[0160] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0161]

[0162] (1) In a 250 mL three-necked flask, 13 g (110 mmol) of compound A-1, 16.9 g (100 mmol) of B-2, and 2.5 g (10 mmol) of p-toluenesulfonic acid pyridine salt were added to 100 mL of dichloromethane. A water separation apparatus was set up, and the mixture was heated to 40 °C and refluxed for 2 h to separate the water. After cooling to room temperature, 150 mL of water was added for lysis. The aqueous phase was extracted with 2 × 100 mL of dichloromethane, and the organic phases were combined. The mixture was washed with 3 × 80 mL of water, and the solvent was concentrated and evaporated at 40 °C to obtain 20.1 g of light yellow oily liquid C-2.

[0163] Compound C-1 has a purity of 98.6% (including cis and trans) and a yield of 90.3%.

[0164] (2) Add 20.1g (90mmol) of compound C-2, 27.1g (88mmol) of compound D-1, 16.6g (120mmol) of potassium carbonate and 1.5g (9mmol) of potassium iodide to a 500ml three-necked flask containing 150mL of dimethylformamide and react at 90℃ for 2h.

[0165] (3) Post-treatment: Cool to room temperature, add 300 mL of water, stir, filter, and slurry the filter cake three times with 3 x 100 mL of water and once with 100 mL of ethanol. Filter and dry. Spread 15 g of 200-300 mesh silica gel, concentrate the product, dissolve it in petroleum ether, pass it through a column, evaporate the solvent at 50 °C to obtain 33 g of white solid. Add toluene:ethanol = 2:4, recrystallize, freeze at -30 °C for 3 h, filter through a Buchner funnel, and dry to obtain 30.1 g of white solid.

[0166] Compound P-1 purity: 99.95%; yield: 76%.

[0167] The target product was characterized by mass spectrometry (MS), M+(450): 41(10%), 55(28%), 83(37%), 129(100%), 251(23%), 252(9%), 450(31%), 451(9%).

[0168] Example 4

[0169] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0170]

[0171] The preparation method is described in Example 3.

[0172] Compound P-2 purity: 99.9%; yield: 72.5%.

[0173] The target product was characterized by mass spectrometry (MS). M+(462): 41 (10%), 55 (28%), 69 (65%), 83 (37%), 84 (42%), 129 (100%), 319 (35%), 320 (14%), 462 (31%), 463 (7%).

[0174] Example 5

[0175] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0176]

[0177] The preparation method is the same as in Example 1.

[0178] Compound P-3 purity: 99.93%; yield: 78.7%.

[0179] The target product was characterized by mass spectrometry (MS). M+(532): 41 (10%), 55 (28%), 69 (65%), 91 (73%), 129 (100%), 251 (43%), 252 (57%), 342 (23%), 394 (21%), 484 (51%), 485 (11%).

[0180] Example 6

[0181] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound, the preparation method comprising:

[0182]

[0183] The preparation method is described in Example 3.

[0184] Compound P-4 purity: 99.9%; yield: 72.5%.

[0185] The target product was characterized by mass spectrometry (MS), M+(462): 41 (10%), 55 (28%), 125 (37%), 211 (100%), 251 (35%), 252 (11%), 308 (25%), 532 (8%).

[0186] Example 7

[0187] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound. The only difference between this method and the preparation method in Example 1 is that in step (2), cesium carbonate is replaced with potassium tert-butoxide in equal amounts, while other operations remain unchanged.

[0188] Compound P-2 purity: 99.89%; yield: 73%.

[0189] Example 8

[0190] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound. The only difference between this method and the preparation method in Example 1 is that in step (2), cesium carbonate is replaced with sodium carbonate in equal amounts, while other operations remain unchanged.

[0191] Compound P-2 purity: 99.92%; yield: 75%.

[0192] Example 9

[0193] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound. The only difference between this method and the preparation method in Example 1 is that in step (2), potassium iodide is replaced with an equal amount of 18-crown-6-ether, while other operations remain unchanged.

[0194] Compound P-2 purity: 99.93%; yield: 75%.

[0195] Example 10

[0196] This embodiment provides a method for preparing a dioxane-containing negative liquid crystal compound. The only difference between this method and the preparation method in Example 1 is that in step (2), potassium iodide is replaced with sodium iodide in equal amounts, while other operations remain unchanged.

[0197] Compound P-2 purity: 99.92%; yield: 73.5%.

[0198] For ease of explanation, in the following application examples, the group structures of each component in the liquid crystal composition are represented by the codes listed in Table 1:

[0199] Table 1

[0200]

[0201]

[0202] Application Example 1

[0203] This application example provides a liquid crystal composition, the composition of which is as follows:

[0204] Component Code Percentage by mass (%) 3CCV 40 5PP1 8 3C1OWO2 10 5C1OWO2 10 2CC1OWO2 10 3CC1OWO2 10 2CPWO2 4 3CPWO2 4 3CD1OB(S)O4 4

[0205] Application Example 2

[0206] This application example provides a liquid crystal composition, the composition of which is as follows:

[0207]

[0208]

[0209] Application Example 3

[0210] This application example provides a liquid crystal composition, the composition of which is as follows:

[0211] Component Code Percentage by mass (%) 3CCV 40 5PP1 8 3C1OWO2 10 5C1OWO2 10 2CC1OWO2 9 3CC1OWO2 9 2CPWO2 4 3CPWO2 4 3D1OB(S)OCF3 6

[0212] Application Example 4

[0213] This application example provides a liquid crystal composition, the composition of which is as follows:

[0214] Component Code Percentage by mass (%) 3CCV 40 5PP1 8 3C1OWO2 10 5C1OWO2 10 2CC1OWO2 8 3CC1OWO2 9 2CPWO2 4 3CPWO2 4 3D1OB(S)O2V(2F) 7

[0215] Comparative Application Example 1

[0216] This comparative application example provides a liquid crystal composition, the composition of which is as follows:

[0217] Component Code Percentage by mass (%) 3CCV 40 5PP1 8 3C1OWO2 10 5C1OWO2 10 2CC1OWO2 10 3CC1OWO2 10 2CPWO2 4 3CPWO2 4 3DC1OB(S)O4 4

[0218] Comparative Application Example 2

[0219] This comparative application example provides a liquid crystal composition, the composition of which is as follows:

[0220] The only difference from Example 1 is that the compound with component code 3CD1OB(S)O4 is replaced in equal amounts with Other components and their contents remain unchanged.

[0221] Component Code Percentage by mass (%) 3CCV 40 5PP1 8 3C1OWO2 10 5C1OWO2 10 2CC1OWO2 10 3CC1OWO2 10 2CPWO2 4 3CPWO2 4 3DC1OPGN 4

[0222] Test Example 1

[0223] The abbreviations and test methods used in the test projects are shown in Table 2.

[0224] Table 2

[0225]

[0226]

[0227] The results are shown in Table 3.

[0228] Table 3

[0229] Cp Δn Δε γ1 t(-30℃) Application Example 1 88 0.115 -3.83 92 ＞1000 Application Example 2 82 0.110 -3.84 89 ＞1000 Application Example 3 83 0.110 -3.74 90 ＞1000 Application Example 4 80 0.112 -3.81 87 ＞1000 Comparative Application Example 1 80 0.112 -3.72 93 ＞1000 Comparative Application Example 2 76 0.110 2.75 95 ＞1000

[0230] The applicant declares that this invention illustrates a dioxane-containing negative liquid crystal compound, its preparation method, and its application through the above embodiments. However, this invention is not limited to the above embodiments, meaning that this invention does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials, additions of auxiliary components, and selection of specific methods, etc., all fall within the protection and disclosure scope of this invention.

[0231] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0232] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not describe the various possible combinations separately.

Claims

1. A dioxane-containing negative liquid crystal compound, characterized in that, The compound has the structure shown in Formula I: Wherein, G1 and G2 are each independently selected from hydrogen, C1-C12 alkyl, at least one C1-C12 alkyl group substituted with oxygen, sulfur, carbonyl, olefin or alkyne, C1-C12 alkoxy group, at least one C1-C12 alkoxy group substituted with oxygen, sulfur, carbonyl, olefin or alkyne. Cycloaca A is selected from 1,4-cyclohexyl, cyclopentyl, cyclopentenyl, 1,4-cyclohexenyl, cyclobutyl, and glycidyl, wherein one or more hydrogen atoms in 1,4-cyclohexyl, cyclopentyl, cyclopentenyl, 1,4-cyclohexenyl, cyclobutyl, and glycidyl are substituted with fluorine, chlorine, methyl, trifluoromethyl, ethyl, or methoxy. n is selected from 0, 1, or 2; Y is selected from O or S; X2 and X3 are each independently selected from hydrogen, fluorine, chlorine, methyl, or methoxy.

2. The dioxane-containing negative liquid crystal compound according to claim 1, characterized in that, The structure of the compound is selected from any one of the following structures:

3. The dioxane-containing negative liquid crystal compound according to claim 1 or 2, characterized in that, The compound is selected from any one of the following:

4. The method for preparing the dioxane-containing negative liquid crystal compound according to any one of claims 1-3, characterized in that, The preparation method includes: (1) React the compound shown in Formula II with the compound shown in Formula III to obtain the compound shown in Formula IV; X1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy or methanesulfonyloxy; (2) The compound shown in Formula IV is reacted with the compound shown in Formula V to obtain the product; 5. The preparation method according to claim 4, characterized in that, Step (1) involves reacting under the conditions of a first organic solvent and a dehydrating agent; Preferably, the molar ratio of the compound represented by Formula II to the compound represented by Formula III is (0.8-2):1, and more preferably (0.9-1.2):1; Preferably, the molar ratio of the compound represented by Formula III, the first organic solvent, and the dehydrating agent is 1:(3-20):(0.05-1), more preferably 1:(3-10):(0.05-1); Preferably, the reaction temperature in step (1) is 40-110℃ and the reaction time is 0.5-24h; Preferably, the first organic solvent includes any one or a combination of at least two of dichloromethane, dichloroethane, petroleum ether, n-heptane, toluene, and xylene; Preferably, the first organic solvent comprises any one or a combination of at least two of dichloromethane, petroleum ether, n-heptane, or toluene; Preferably, the dehydrating agent comprises any one or a combination of at least two of the following: a saturated solution of p-toluenesulfonic acid, p-toluenesulfonic acid pyridinium salt, or hydrochloric acid chloride salt; Preferably, the dehydrating agent comprises toluenesulfonic acid and / or p-toluenesulfonic acid pyridine salt.

6. The preparation method according to claim 4 or 5, characterized in that, Step (2) involves the reaction under the conditions of a second organic solvent and a catalyst; Preferably, the molar ratio of the compound represented by Formula IV to the compound represented by Formula V is (0.9-2):1, and more preferably (0.9-1.2):1; Preferably, the molar ratio of the compound represented by Formula V, the second organic solvent, and the catalyst is 1:(3-20):(0.05-1), more preferably 1:(3-10):(0.05-0.5); Preferably, step (2) is performed under alkaline conditions; Preferably, the alkali includes any one or a combination of at least two of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, and potassium tert-butoxide.

7. The preparation method according to any one of claims 4-6, characterized in that, The temperature in step (2) is 40-130℃, and the time is 0.5-24h; Preferably, the second organic solvent comprises any one or a combination of at least two of toluene, n-heptane, acetonitrile, tetrahydrofuran, dimethylformamide, and dimethylacetamide; Preferably, the catalyst comprises any one or a combination of at least two of sodium iodide, potassium iodide, tetrabutylammonium bromide, and 18-crown-6-ether.

8. A liquid crystal composition, characterized in that, The liquid crystal composition comprises any one of the dioxane-containing negative liquid crystal compounds according to claims 1-3.

9. The liquid crystal composition according to claim 8, characterized in that, The liquid crystal composition further includes at least one compound of general formula M, at least one compound of general formula A1, and at least one compound of general formula A2; R M1 and R M2 Each can independently represent -H, a straight-chain or branched alkyl group containing 1-12 carbon atoms, One or more non-adjacent -CH2- atoms in the straight-chain or branched alkyl group containing 1-12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-. R A1 and R A2 Each independently represents a straight-chain or branched alkyl group containing 1-12 carbon atoms. One or more non-adjacent -CH2- atoms in the straight-chain or branched alkyl group containing 1-12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-, and the straight-chain or branched alkyl group containing 1-12 carbon atoms... One or at least two -H can be independently replaced by -F or -Cl; Z M1 and Z M2 Each can independently represent a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, or -(CH2)4-; Z A11 Z A21 and Z A22 Each can independently represent a single bond, -CH2CH2-, -CF2CF2-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -CF=CF-, -CH2O-, or -OCH2-; L A11 L A12 L A13 L A21 and L A22 Each can independently represent -H, an alkyl group containing 1-3 carbon atoms, or a halogen; X A1 and X A2 Each can independently represent a halogen, a haloalkyl or haloalkoxy group containing 1-5 carbon atoms, or a haloalkenyl or haloalkenoxy group containing 2-5 carbon atoms. ring ring and ring Each represents independently in, One or at least two of the -CH2- can be replaced by -O-. At most one -H in the halogen can be replaced by a halogen; ring ring ring and ring Each represents independently in, One or more of the -CH2- bonds can be replaced by -O- bonds, and one or more single bonds in a ring can be replaced by double bonds. One or more of the -H can be replaced by -CN, -F or -Cl, and -CH= in one or more of the rings can be replaced by -N=; n M1 n A11 and n A2 Each can independently represent 0, 1, 2, or 3, and when n M1 When = 2 or 3, the ring They can be the same or different, Z M2 They can be the same or different; when n A11 When = 2 or 3, the ring They can be the same or different, Z A11 They can be the same or different; when n A2 When = 2 or 3, the ring They can be the same or different, Z A21 They can be the same or different; n A12 Represents 1 or 2, and when n A12 When = 2, ring They can be the same or different; Preferably, the compound of general formula M accounts for 0.1%-90% of the weight percentage of the liquid crystal composition, the compound of general formula A-1 accounts for 0.1%-80% of the weight percentage of the liquid crystal composition, and the compound of general formula A-2 accounts for 0.1%-80% of the weight percentage of the liquid crystal composition.

10. The use of the dioxane-containing negative liquid crystal compound according to any one of claims 1-3 or the liquid crystal composition according to claim 8 or 9 in the preparation of liquid crystal display devices.

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