TWI882649B - Liquid crystal compound and its application - Google Patents

Abstract

The present invention discloses a liquid crystal compound, the structure of which is shown in the following formula I: The liquid crystal compound has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K. The liquid crystal composition of the present invention has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K, and can be used to develop a liquid crystal display element or liquid crystal display with a faster response speed and can effectively improve afterimages.

Description

Liquid crystal compound and its application

The present invention relates to the field of liquid crystal display technology, and specifically comprises a liquid crystal compound, a liquid crystal composition comprising the liquid crystal compound, and a liquid crystal display element or display thereof.

F. Rein Itzer first observed the phenomenon of liquid crystal in 1888. This Austrian biologist discovered when heating cholesterol benzoic acid crystals that when the temperature rose to 145.5 ℃, the crystals melted into a milky white viscous liquid. When the temperature was further heated to 178.5 ℃, the milky white viscous liquid became a completely transparent liquid. The following year, Reinitzer sent the above sample to O. Lehmann in Germany and asked him to test it. Lehmann confirmed that this substance exhibited optical anisotropy, and based on the characteristics of this "liquid with both liquid fluidity and crystal optical anisotropy", he suggested calling it "liquid crystal". Ordinary inorganic or organic crystal molecules are regularly arranged at the lattice nodes, forming the so-called lattice array, which is three-dimensionally ordered. The "liquid crystal" structure gives the crystal anisotropy, such as optical anisotropy, dielectric anisotropy, and dielectric magnetic anisotropy.

With the rapid development of science and technology, people apply liquid crystal to the display field, and the application is becoming more and more extensive, mainly in mobile phones, computers, televisions, car-mounted, outdoor displays, medical equipment and other display terminals. With the development of display technology, liquid crystal display devices (LCD) and other flat panel display devices have become the mainstream of display devices due to their advantages such as high image quality, power saving, thin body and wide application range, and eventually replaced cathode ray tube displays.

Liquid crystal displays are classified into TN (twist nematic), STN (super twisted nematic), IPS (In-plane switching), VA (vertical alignment) and other types according to the type of display mode.

Liquid crystal materials have low rotational viscosity, which is beneficial to improve the response speed of liquid crystal display devices and shorten the response time. High clearing point can increase the upper limit of the operating temperature of liquid crystal display devices and help improve thermal stability; good low-temperature miscibility can reduce the lower limit of the operating temperature of liquid crystal display devices, allowing them to work normally at very low temperatures; at the same time, they have a high upper limit and a low lower limit of the operating temperature, which can obtain a wider operating temperature range. Higher optical anisotropy can increase the response speed by reducing the panel gap on the basis of the same light delay design. High elastic constant is also an important factor in improving response speed. Higher dielectric anisotropy can reduce the driving voltage of liquid crystal display devices and reduce energy consumption. Good light and heat stability make liquid crystal display devices have good stability to high temperature, ultraviolet light or visible light, and are not prone to defects such as afterimages, which can extend the service life. Since liquid crystal compounds are generally sensitive to ultraviolet rays, conventional liquid crystal materials are usually combined with anti-UV additives to avoid damage caused by ultraviolet rays. Although anti-UV additives improve the anti-UV performance of liquid crystals after being added to liquid crystal compositions, they have no obvious effect on improving image quality. The addition of some compounds also affects low-temperature stability.

Response time refers to the time it takes for a liquid crystal cell to go from emitting light to not emitting light and then back to the emitting state, that is, the time it takes for a picture element to turn from black to white and then back to black (the principle is to apply voltage to the liquid crystal molecules to make the liquid crystal molecules twist and recover). The response time is calculated in milliseconds (ms, milliseconds). The longer the response time is, the slower the LCD screen will respond. If analyzed from a theoretical perspective, a DVD movie video with a response time of 30 to 40 milliseconds can be played with a good display effect on an LCD with a response time of 30 to 40 milliseconds. For 3D games with higher frames per second, the response time requirement will be higher, 16 milliseconds or even faster 12 milliseconds. At this time, IPS hard screen LCD can show its advantages. The shorter the response time, the less we will feel the tail trailing when watching dynamic images.

Regarding the response speed of liquid crystal, from the principle characteristics of liquid crystal display, the following factors generally affect the response speed of liquid crystal display: 1. The viscosity coefficient of liquid crystal material, which is determined by the characteristics of the material itself; 2. The size of the gap between the liquid crystal unit cell, that is, the gap between the upper and lower conductive glass substrates, that is, the thickness of the liquid crystal layer; 3. The dielectric constant of liquid crystal material, which is determined by the characteristics of the material itself; 4. Driving voltage, among which, the higher the driving voltage, the faster the response speed.

Among them, the viscosity coefficient of liquid crystal materials and the dielectric constant of liquid crystal materials are directly related to the characteristics of the liquid crystal materials themselves. Increasing the driving voltage of the liquid crystal unit box can certainly increase the response speed, but at the same time it will also reduce the life of the liquid crystal. By improving the process, the gap of the liquid crystal unit box can be reduced, so that the liquid crystal molecules can twist into place faster. Of course, these characteristics are all relative characteristics at room temperature. Since the liquid crystal materials in actual use are composed of many different types of polymer organic substances, they maintain the common characteristics of liquids and solids within a certain temperature range. When the temperature changes, the activity energy of the liquid crystal molecules changes, and the viscosity coefficient of the corresponding liquid crystal material changes; when the temperature is high, the activity energy of the liquid crystal molecules is high and the viscosity coefficient is small. When driven by an electric field, the liquid crystal can freely and quickly twist and arrange in the direction of the electric field, and the response speed of the display is accelerated; similarly, under low temperature conditions, the activity energy of the liquid crystal molecules is weakened, and the viscosity coefficient becomes larger. When an electric field is applied to the liquid crystal molecules, the liquid crystal molecules are subject to greater viscosity resistance, and the liquid crystal is twisted and arranged in the direction of the electric field when driven by the electric field, and the response speed of the display is slowed down. If the speed is too slow, ghosting will occur.

Therefore, developing liquid crystal media with large dielectric anisotropy Δε, high elastic constant K, and good low-temperature miscibility is a technical problem that needs to be solved urgently.

In view of this, the present invention provides a liquid crystal compound, a liquid crystal composition and a liquid crystal display element or display thereof. The liquid crystal compound has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K. The liquid crystal composition comprising the present invention has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K, and can be used to develop a liquid crystal display element or liquid crystal display with a faster response speed and can effectively improve afterimages.

In order to achieve the above-mentioned purpose of the invention, the present invention adopts the following technical solutions:

The first aspect of the present invention provides a liquid crystal compound, the general structural formula of the compound is as shown in Formula I, Ⅰ wherein R represents an alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the alkyl group may be substituted by halogen; and/or any one or more -CH ₂ - in the alkyl group may be independently substituted by -C≡C-, -CH＝CH-, , , , , -O-, -S-, -CO-O- or -O-CO-, in such a way that the O or S atoms are not directly connected to each other; express , , , or ; express , and any hydrogen in the group may be substituted by fluorine; m represents 0, 1 or 2, and when m is 2, the two can be the same or different; n represents 0, 1 or 2, and when n is 2, the two Any of the following: same or different; m+n≥1.

A second aspect of the present invention provides a liquid crystal composition, which includes the above-mentioned liquid crystal compound.

The cooperative manufacturer of the present invention provides a liquid crystal display element or a liquid crystal display, wherein the liquid crystal display element or the liquid crystal display comprises the aforementioned liquid crystal compound and a liquid crystal composition.

The beneficial effects of the present invention are as follows:

The liquid crystal compound of the present invention has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K. The liquid crystal composition containing the present invention has a large dielectric anisotropy Δε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity _γ1 and a large elastic constant K, and can be used to develop a liquid crystal display element or liquid crystal display with a faster response speed and can effectively improve afterimages.

The present invention provides a liquid crystal compound, the general structural formula of the compound is shown in Formula I, Ⅰ wherein R represents an alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the alkyl group may be substituted by halogen; and/or any one or more -CH ₂ - in the alkyl group may be independently substituted by -C≡C-, -CH＝CH-, , , , , -O-, -S-, -CO-O- or -O-CO-, in such a way that the O or S atoms are not directly connected to each other; express , , , or ; express , and any hydrogen in the group may be substituted by fluorine; m represents 0, 1 or 2, and when m is 2, the two can be the same or different; n represents 0, 1 or 2, and when n is 2, the two Any of the following: same or different; m+n≥1.

The liquid crystal compound of the present invention is preferably a compound represented by the aforementioned formula I selected from the group consisting of compounds represented by the following formulas I-1 to I-27, Ⅰ-1 Ⅰ-2 Ⅰ-3 Ⅰ-4 Ⅰ-5 Ⅰ-6 Ⅰ-7 Ⅰ-8 Ⅰ-9 Ⅰ-10 Ⅰ-11 Ⅰ-12 Ⅰ-13 Ⅰ-14 Ⅰ-15 I-16 Ⅰ-17 Ⅰ-18 Ⅰ-19 Ⅰ-20 Ⅰ-21 Ⅰ-22 I-23 Ⅰ-24 Ⅰ-25 I-26 I-27 wherein R represents an alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the alkyl group may be substituted with halogen; and/or any one or more -CH ₂ - in the alkyl group may be independently substituted with -C≡C-, -CH＝CH-, , , , , -O-, -S-, -CO-O- or -O-CO- in such a way that the O or S atoms are not directly connected to each other.

The liquid crystal compound of the present invention is preferably any one or any combination of the compounds represented by the aforementioned formulas I-1 to I-27 selected from the following compounds represented by the following formulas I-1-1 to I-27-1. Ⅰ-1-1 Ⅰ-1-2 Ⅰ-2-1 Ⅰ-2-2 Ⅰ-3-1 Ⅰ-3-2 Ⅰ-4-1 Ⅰ-4-2 Ⅰ-5-1 Ⅰ-5-2 Ⅰ-6-1 Ⅰ-6-2 Ⅰ-7-1 Ⅰ-7-2 Ⅰ-8-1 Ⅰ-8-2 Ⅰ-9-1 Ⅰ-9-2 Ⅰ-10-1 Ⅰ-10-2 Ⅰ-11-1 Ⅰ-11-2 Ⅰ-12-1 Ⅰ-12-2 Ⅰ-13-1 Ⅰ-13-2 Ⅰ-14-1 Ⅰ-14-2 Ⅰ-15-1 Ⅰ-15-2 Ⅰ-16-1 Ⅰ-16-2 Ⅰ-17-1 Ⅰ-17-2 Ⅰ-18-1 Ⅰ-18-2 Ⅰ-19-1 Ⅰ-19-2 Ⅰ-20-1 Ⅰ-20-2 Ⅰ-21-1 Ⅰ-21-2 Ⅰ-22-1 Ⅰ-22-2 Ⅰ-23-1 Ⅰ-23-2 Ⅰ-24-1 Ⅰ-24-2 Ⅰ-25-1 Ⅰ-25-2 Ⅰ-26-1 Ⅰ-27-1.

The present invention provides a liquid crystal composition. Preferably, the liquid crystal composition comprises one or more liquid crystal compounds of formula I.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula I contains at least one or more compounds represented by formula I-19; further preferably, the compound represented by the aforementioned formula I contains at least two compounds represented by formula I-19.

The liquid crystal composition of the present invention, preferably, comprises the compound represented by formula I-19, which can effectively improve the mutual solubility of the liquid crystal composition while maintaining appropriate dielectric anisotropy, and has a relatively large elastic constant anisotropy.

The liquid crystal composition of the present invention preferably comprises the compound represented by formula I-19-2 in an amount of 1-9% by mass; further preferably, comprises the compound represented by formula I-19-2 in an amount of 1-5% by mass.

The liquid crystal composition of the present invention preferably contains 1-5% by weight of the compound represented by formula Ⅰ-22-2.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula II. Ⅱ Wherein, R ₃ represents an alkyl group having 1 to 10 carbon atoms; R ₄ represents an alkenyl group having 2 to 10 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula II is selected from the group consisting of compounds represented by the following formulae II-1 to II-7, Ⅱ-1 Ⅱ-2 Ⅱ-3 Ⅱ-4 Ⅱ-5 Ⅱ-6 Ⅱ-7.

The liquid crystal composition of the present invention preferably comprises 20-50% by weight of the compound represented by formula II-1, and more preferably comprises 35-45% by weight of the compound represented by formula II-1.

The liquid crystal composition of the present invention preferably comprises the compound represented by formula II-3 in an amount of 1-9% by weight, and more preferably comprises the compound represented by formula II-3 in an amount of 4-7% by weight.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula III, III wherein R ₅ represents a chain alkyl group having 1 to 15 carbon atoms, and one or more non-adjacent -CH ₂ - in R ₅ are optionally substituted by cyclopentylene or cyclopropylene; Xa represents H or CH ₃ ; Each independently expresses , , , or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III is selected from the group consisting of compounds represented by the following formulae III-1 to III-10, III-1 III-2 III-3 III-4 III-5 III-6 III-7 III-8 III-9 III-10

Wherein, R ₅ represents a chain alkyl group having 1 to 15 carbon atoms, and one or more non-adjacent -CH ₂ - in R ₅ is optionally substituted by a cyclopentylene group or a cyclopropylene group.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-1 is selected from the group consisting of compounds represented by the following formulae III-1-1 to III-1-6, III-1-1 III-1-2 III-1-3 III-1-4 III-1-5 Ⅲ-1-6.

In the liquid crystal composition of the present invention, preferably, the mass content of the compound represented by the aforementioned formula III-1-2 is 2-7%; preferably, the mass content of the compound represented by the aforementioned formula III-1-4 is 1-13%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-2 is selected from the group consisting of compounds represented by the following formulae III-2-1 to III-2-4, III-2-1 III-2-2 III-2-3 Ⅲ-2-4.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula III-2-3 of 0-7%, and more preferably, has a mass content of the compound represented by the aforementioned formula III-2-3 of 3-5%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-3 is selected from the group consisting of compounds represented by the following formulae III-3-1 to III-3-5, III-3-1 III-3-2 III-3-3 III-3-4 Ⅲ-3-5.

In the liquid crystal composition of the present invention, preferably, the mass content of the compound represented by the aforementioned formula III-3-3 is 2-7%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-4 is selected from the group consisting of compounds represented by the following formulae III-4-1 to III-4-5, III-4-1 III-4-2 III-4-3 III-4-4 Ⅲ-4-5.

The liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-4 is selected from the group consisting of compounds represented by formula III-4-1, III-4-2, and III-4-5, and the mass content of each compound represented by formula III-4-1, III-4-2, and III-4-5 is 1-10%; further preferably, the mass content of each compound is 2-5%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III-5 is selected from the group consisting of compounds represented by the following formulae III-5-1 to III-5-4, III-5-1 III-5-2 III-5-3 Ⅲ-5-4.

In the liquid crystal composition of the present invention, preferably, the mass content of the compound represented by the aforementioned formula III-5-2 is 1-7%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula IV. IV wherein R ₆ represents a chain alkyl group having 1 to 10 carbon atoms; express , or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IV is selected from the group consisting of compounds represented by the following formulas IV-1 and IV-2. IV-1 IV-2 wherein R ₆ represents a chain alkyl group having 1 to 10 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IV-1 is selected from the group consisting of compounds represented by the following formulae IV-1-1 to IV-1-5, IV-1-1 IV-1-2 IV-1-3 IV-1-4 IV-1-5.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula IV-1-3 of 0-15%, and more preferably, has a mass content of the compound represented by the aforementioned formula IV-1-3 of 3-9%.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula IV-1-4 of 0-15%, and more preferably, has a mass content of the compound represented by the aforementioned formula IV-1-4 of 3-9%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IV-2 is selected from the group consisting of compounds represented by the following formulae IV-2-1 to IV-2-5, IV-2-1 IV-2-2 IV-2-3 IV-2-4 IV-2-5.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula IV-2-3 of 0-15%, and more preferably, has a mass content of the compound represented by the aforementioned formula IV-2-3 of 3-9%.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula IV-2-4 of 0-15%, and more preferably, has a mass content of the compound represented by the aforementioned formula IV-2-4 of 3-9%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula V. Ⅴ wherein R ₇ represents an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, F, CF ₃ or OCF ₃ ; and R ₈ represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula V is selected from the group consisting of compounds represented by the following formulas V-1 to V-30, Ⅴ-1 Ⅴ-2 Ⅴ-3 Ⅴ-4 Ⅴ-5 Ⅴ-6 Ⅴ-7 Ⅴ-8 Ⅴ-9 Ⅴ-10 Ⅴ-11 Ⅴ-12 Ⅴ-13 Ⅴ-14 Ⅴ-15 Ⅴ-16 Ⅴ-17 Ⅴ-18 Ⅴ-19 Ⅴ-20 Ⅴ-21 Ⅴ-22 Ⅴ-23 Ⅴ-24 Ⅴ-25 Ⅴ-26 Ⅴ-27 Ⅴ-28 Ⅴ-29 Ⅴ-30.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula V-1 of 1-11%; a mass content of the compound represented by the aforementioned formula V-3 of 1-18%; a mass content of the compound represented by the aforementioned formula V-4 of 1-10%; a mass content of the compound represented by the aforementioned formula V-11 of 1-11%; a mass content of the compound represented by the aforementioned formula V-14 of 1-10%, and further preferably, a mass content of the compound represented by the aforementioned formula V-14 of 4-9%; and a mass content of the compound represented by the aforementioned formula V-16 of 2-9%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula VI. VI wherein R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms; express , or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VI is selected from the group consisting of compounds represented by the following formulae VI-1 to VI-3, VI-1 VI-2 VI-3 wherein R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VI-1 is selected from the group consisting of compounds represented by the following formulae VI-1-1 to VI-1-7, VI-1-1 VI-1-2 VI-1-3 VI-1-4 VI-1-5 VI-1-6 VI-1-7.

The liquid crystal composition of the present invention preferably comprises a compound of formula VI-1-1 with a mass content of 1-13%; preferably comprises a compound of formula VI-1-5 with a mass content of 1-10%; preferably comprises a compound of formula VI-1-6 with a mass content of 1-15%; preferably comprises a compound of formula VI-1-7 with a mass content of 1-17%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VI-2 is selected from the group consisting of compounds represented by the following formulae VI-2-1 to VI-2-10, VI-2-1 VI-2-2 VI-2-3 VI-2-4 VI-2-5 VI-2-6 VI-2-7 VI-2-8 VI-2-9 VI-2-10.

The liquid crystal composition of the present invention preferably comprises a compound of formula VI-2-1 with a mass content of 1-9%; preferably, comprises a compound of formula VI-2-2 with a mass content of 1-12%; preferably, comprises a compound of formula VI-2-4 with a mass content of 1-15%; preferably, comprises a compound of formula VI-2-5 with a mass content of 2-12%; preferably, comprises a compound of formula VI-2-10 with a mass content of 2-13%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VI-3 is selected from the group consisting of compounds represented by the following formulae VI-3-1 to VI-3-7, VI-3-1 VI-3-2 VI-3-3 VI-3-4 VI-3-5 VI-3-6 VI-3-7.

The liquid crystal composition of the present invention preferably has a mass content of the compound represented by the aforementioned formula VI-3-1 of 1-13%, and further preferably has a mass content of the compound represented by the aforementioned formula VI-3-1 of 5-9%; the mass content of the compound represented by the aforementioned formula VI-3-3 of 5-13%; the mass content of the compound represented by the aforementioned formula VI-3-6 of 5-13%; and the mass content of the compound represented by the aforementioned formula VI-3-7 of 2-13%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula VII. VII wherein Ra represents a chain alkyl group having 1 to 15 carbon atoms; Rb represents a chain alkyl group having 1 to 15 carbon atoms, a chain alkoxy group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms; express or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VII is selected from the group consisting of compounds represented by the following formulae VII-1 to VII-18, VII-1 VII-2 VII-3 VII-4 VII-5 VII-6 VII-7 VII-8 VII-9 VII-10 VII-11 VII-12 VII-13 VII-14 VII-15 VII-16 VII-17 Ⅶ-18.

In the liquid crystal composition of the present invention, preferably, the mass content of the compound represented by the aforementioned formula VII-6 is 1-5%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula VIII. VIII wherein Rc represents a chain alkyl group having 1 to 15 carbon atoms; X ₁ , X ₂ , and X ₃ each independently represent H or F, and at least one of X ₁ , X ₂ , and X ₃ represents F.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VIII is selected from the group consisting of compounds represented by the following formulas VIII-1 and VIII-2. Ⅷ-1 VIII-2 wherein Rc represents a chain alkyl group having 1 to 15 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VIII-1 is selected from the group consisting of compounds represented by the following formulas VIII-1-1 to VIII-1-4, Ⅷ-1-1 Ⅷ-1-2 Ⅷ-1-3 Ⅷ-1-4.

In the liquid crystal composition of the present invention, preferably, the mass content of the compound represented by the aforementioned formula VIII-1-2 is 1-7%; preferably, the mass content of the compound represented by the aforementioned formula VIII-1-3 is 1-7%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula VIII-2 is selected from the group consisting of compounds represented by the following formulas VIII-2-1 to VIII-2-3, Ⅷ-2-1 Ⅷ-2-2 Ⅷ-2-3.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula IX-1 or IX-2. Ⅸ-1 IX-2 wherein Rd and Re each independently represent a chain alkyl group having 1 to 15 carbon atoms, wherein one or more non-adjacent -CH ₂ - in Rd and Re are optionally substituted by cyclopentylene or cyclopropylene; , Each independently expresses , or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IX-1 is selected from the group consisting of compounds represented by the following formulas IX-1-1 to IX-1-11, Ⅸ-1-1 Ⅸ-1-2 Ⅸ-1-3 Ⅸ-1-4 Ⅸ-1-5 Ⅸ-1-6 Ⅸ-1-7 Ⅸ-1-8 Ⅸ-1-9 Ⅸ-1-10 Ⅸ-1-11.

The liquid crystal composition of the present invention preferably comprises a compound of formula IX-1-1 with a mass content of 1-11%; preferably, comprises a compound of formula IX-1-2 with a mass content of 1-15%; preferably, comprises a compound of formula IX-1-3 with a mass content of 1-9%; preferably, comprises a compound of formula IX-1-4 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-5 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-6 with a mass content of 1-10%; preferably, comprises a compound of formula IX-1-8 with a mass content of 1-9%; preferably, comprises a compound of formula IX-1-9 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-10 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-11 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-12 with a mass content of 1-13%; preferably, comprises a compound of formula IX-1-13 with a mass content of 1-13% % of the compound represented by formula IX-1-11.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IX-2 is selected from the group consisting of compounds represented by the following formulas IX-2-1 to IX-2-3, Ⅸ-2-1 Ⅸ-2-2 Ⅸ-2-3.

The liquid crystal composition of the present invention preferably comprises a compound represented by formula IX-2-1 in an amount of 0.05-4.5% by mass; preferably comprises a compound represented by formula IX-2-3 in an amount of 0.05-4.5% by mass.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula X. Ⅹ wherein Rf represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms; _X4 represents H or F; _X5 represents F or _OCF3 ; a represents 1 or 2; express or , when a represents 2, Can be the same or different.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X is selected from the group consisting of compounds represented by the following formulas X-1 to X-4, Ⅹ-1 Ⅹ-2 Ⅹ-3 X-4 wherein Rf represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms; and _X4 represents H or F.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X-1 is selected from the group consisting of compounds represented by the following formulae X-1-1 to X-1-5, Ⅹ-1-1 Ⅹ-1-2 Ⅹ-1-3 Ⅹ-1-4 Ⅹ-1-5.

The liquid crystal composition of the present invention preferably comprises a compound of formula X-1-1 with a mass content of 3-13%; preferably, comprises a compound of formula X-1-2 with a mass content of 3-9%; preferably, comprises a compound of formula X-1-3 with a mass content of 1-16%; preferably, comprises a compound of formula X-1-4 with a mass content of 3-11.5%; preferably, comprises a compound of formula X-1-5 with a mass content of 2-13%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X-2 is selected from the group consisting of compounds represented by the following formulas X-2-1 to X-2-5, Ⅹ-2-1 Ⅹ-2-2 Ⅹ-2-3 Ⅹ-2-4 Ⅹ-2-5.

The liquid crystal composition of the present invention preferably comprises a compound of formula X-2-1 with a mass content of 1-11.5%; preferably, comprises a compound of formula X-2-2 with a mass content of 2-14.5%; preferably, comprises a compound of formula X-2-3 with a mass content of 2-9%; preferably, comprises a compound of formula X-2-4 with a mass content of 1-10.5%; preferably, comprises a compound of formula X-2-5 with a mass content of 2-17%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X-3 is selected from the group consisting of compounds represented by the following formulas X-3-1 to X-3-6, Ⅹ-3-1 Ⅹ-3-2 Ⅹ-3-3 Ⅹ-3-4 Ⅹ-3-5 Ⅹ-3-6.

The liquid crystal composition of the present invention preferably comprises a compound represented by formula X-3-1 with a mass content of 3-15%; preferably comprises a compound represented by formula X-3-2 with a mass content of 2-9.5%; preferably comprises a compound represented by formula X-3-6 with a mass content of 3-12.5%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X-4 is selected from the group consisting of compounds represented by the following formulas X-4-1 to X-4-8, Ⅹ-4-1 Ⅹ-4-2 Ⅹ-4-3 Ⅹ-4-4 Ⅹ-4-5 Ⅹ-4-6 Ⅹ-4-7 Ⅹ-4-8.

The liquid crystal composition of the present invention preferably comprises a compound represented by formula X-4-1 with a mass content of 3-15%; preferably comprises a compound represented by formula X-4-2 with a mass content of 2-9.5%; preferably comprises a compound represented by formula X-4-7 with a mass content of 3-12.5%.

The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula XI. Ⅺ wherein Rg and Rh each independently represent a chain alkyl group having 1 to 15 carbon atoms; Z represents a single bond or -COO-; express or .

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula XI is selected from the group consisting of compounds represented by the following formulas XI-1 and XI-2, Ⅺ-1 XI-2 wherein Rg and Rh each independently represent a chain alkyl group having 1 to 15 carbon atoms.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula XI-1 is selected from the group consisting of compounds represented by the following formulae XI-1-1 to XI-1-3, Ⅺ-1-1 Ⅺ-1-2 Ⅺ-1-3.

In the liquid crystal composition of the present invention, preferably, the mass content of each compound represented by the aforementioned formulae XI-1-1 to XI-1-3 is 0.5-7%, and more preferably, the mass content is 2-5%.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula XI-2 is selected from the group consisting of compounds represented by the following formulae XI-2-1 to XI-2-12, Ⅺ-2-1 Ⅺ-2-2 Ⅺ-2-3 Ⅺ-2-4 Ⅺ-2-5 Ⅺ-2-6 Ⅺ-2-7 Ⅺ-2-8 Ⅺ-2-9 Ⅺ-2-10 Ⅺ-2-11 Ⅺ-2-12.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula X is selected from the combination of the compounds represented by the aforementioned formulas XI-2-2, XI-2-3, and XI-2-4; further preferably, the mass content of each compound represented by the formulas XI-2-2, XI-2-3, and XI-2-4 is 0.5-6%.

Other additives may also be added to the liquid crystal composition of the present invention, such as UV stabilizers, antioxidants, free radical scavengers, etc. The additives that can be listed are as follows: T-1 T-2 T-3 T-4 T-5 T-6 T-7 T-8; wherein u represents an alkylene group having 1 to 20 carbon atoms.

Liquid crystal display element or liquid crystal display

The present invention also provides a liquid crystal display element or a liquid crystal display comprising the liquid crystal compound or liquid crystal composition.

Preferably, the aforementioned liquid crystal display element can be an active matrix addressed liquid crystal display element or a liquid crystal display.

Preferably, the active matrix addressing liquid crystal display element is a VA-TFT, FFS-TFT or IPS-TFT liquid crystal display element.

The liquid crystal display element or liquid crystal display of the present invention comprises the liquid crystal compound and liquid crystal composition of the present invention, and can be used to develop a liquid crystal display element or liquid crystal display with good reliability and a wide operating temperature range.

Embodiment

In order to explain the present invention more clearly, the present invention is further explained below in combination with preferred embodiments. Those skilled in the art should understand that the content described below is illustrative rather than restrictive, and should not be used to limit the scope of protection of the present invention. The embodiments and comparative examples of this specification are provided to more fully explain this specification to those skilled in the art. According to the embodiments and comparative examples of this specification, various different forms can be formed, and the scope of protection of the present invention should not be limited to the embodiments and comparative examples described in detail below.

The method for preparing the compound represented by the aforementioned formula I of the present invention preferably adopts the following synthetic route, and other similar structures can also be prepared by this method.

Embodiment 1

This example provides a liquid crystal compound Ⅰ-1-1, the structure and synthesis route of which are as follows: Ⅰ-1-1

Step 1 Add 3,4-difluoro-6-iodobenzenethiol (20 g, 0.074 mmol), trimethylsilyl acetylenes (7.9 g, 0.081 mmol), sodium acetate (0.8 g, 0.0037 mmol), TMEDA (0.43 g, 0.0037), AgTFA (16 g, 0.08 mmol) into a 500 ml three-necked flask, add 200 ml DMF into the flask, replace the nitrogen three times, heat to 110 °C for 24 hours, then cool to room temperature, pour the reaction solution into 500 ml ice water, extract with ethyl acetate, dry, and concentrate to obtain yellow oily intermediate 1 (14.3 g, 80%).

Step 2 Intermediate 1 (14.3 g, 0.06 mmol), 150 ml methanol, and potassium hydroxide (3.36 g, 0.06 mmol) were added to a 250 ml three-necked flask in sequence and stirred at room temperature for 5 hours. 50 ml water was added to the flask, and the product was extracted with ethyl acetate, dried, and concentrated to obtain a yellow solid intermediate 2 (14.3 g, 80%).

Step 3 After adding intermediate 2 (14.3 g, 0.084 mmol) and THF (150 ml) into a 500 ml three-necked flask, the system was cooled to -78 °C under nitrogen protection, n-butyl lithium (37 ml, 0.092 mmol) was dripped into the system, and the mixture was stirred for 1 hour. Trimethyl borate (10.5 g, 0.1 mmol) was dripped into the reaction, and the mixture was stirred for 30 min. The temperature was then naturally raised to -30 °C, 100 ml of water was added to the system, the pH was adjusted to 4, the liquid was separated, extracted with ethyl acetate, dried, concentrated, slurried with petroleum ether, and filtered to obtain intermediate 3 (15.3 g, 85%)

Step 4 Add 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene (17.3 g, 0.065 mmol), intermediate 3 (15.3 g, 0.071 mmol), potassium carbonate (10.7 g, 0.078 mmol), tetrakistriphenylphosphine palladium (0.03 g, 0.00002 mmol), toluene (150 ml) to a 500 ml three-necked flask, heat and reflux for 3 hours, cool to room temperature, add 100 ml water to the reaction, separate the liquids, pass the toluene phase through a silica gel column, concentrate, and obtain 31 g of yellow oil. Dissolve the oil in 2 times toluene and 1 times ethanol, then crystallize at -30 °C for 2 hours, filter, and obtain Ⅰ-1-1 (15.4 g, 65%), MS (m/z) (M+): 356.14

Embodiment 2

This embodiment provides a liquid crystal compound I-1-2, whose structural formula is as follows: Ⅰ-1-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 1-bromo-4-(4-propylcyclohexyl)-2-fluorobenzene, and the final product Ⅰ-1-2 (16.3 g, yield 63%) is obtained, MS (m/z) (M+): 370.16.

Embodiment 3

This embodiment provides a liquid crystal compound I-2-1, whose structural formula is as follows: Ⅰ-2-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 1-bromo-2-fluoro-4-(4-ethylcyclohexyl)benzene, and the final product Ⅰ-2-1 (15.1 g, yield 54%) is obtained, MS (m/z) (M+): 374.13.

Embodiment 4

This embodiment provides a liquid crystal compound I-2-2, whose structural formula is as follows: Ⅰ-2-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 1-bromo-2-fluoro-4-(4-propylcyclohexyl)benzene, and the final product Ⅰ-2-2 (14.3 g, yield 52%) is obtained, MS (m/z) (M+): 388.15.

Embodiment 5

This embodiment provides a liquid crystal compound I-6-1, whose structural formula is as follows: Ⅰ-6-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 1-bromo-2-fluoro-4-(4-ethylphenyl)benzene, and the final product Ⅰ-6-1 (14.6 g, yield 51%) is obtained, MS (m/z) (M+): 368.08.

Embodiment 6

This embodiment provides a liquid crystal compound I-6-2, whose structural formula is as follows: Ⅰ-6-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 1-bromo-2-fluoro-4-(4-propylphenyl)benzene, and the product Ⅰ-6-2 (15.1 g, yield 53%) is finally obtained, MS (m/z) (M+): 382.10. The MS mass spectrum of the liquid crystal compound Ⅰ-6-2 is shown in Figure 1.

Embodiment 7

This example provides a liquid crystal compound I-8-1, whose structural formula is as follows: Ⅰ-8-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-bromo-1,3-difluoro-5-(4-ethylphenyl)benzene, and the final product Ⅰ-8-1 (12.3 g, yield 47%) is obtained, MS (m/z) (M+): 386.08.

Embodiment 8

This example provides a liquid crystal compound I-8-2, whose structural formula is as follows: Ⅰ-8-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-bromo-1,3-difluoro-5-(4-propylphenyl)benzene, and the final product Ⅰ-8-2 (12.1 g, yield 48%) is obtained, MS (m/z) (M+): 400.09.

Embodiment 9

This embodiment provides a liquid crystal compound I-10-1, whose structural formula is as follows: Ⅰ-10-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-(4-bromo-3-fluorophenyl)-5-ethyltetrahydropyran, and the final product Ⅰ-10-1 (15.7 g, yield 51%) is obtained, MS (m/z) (M+): 376.11.

Embodiment 10

This embodiment provides a liquid crystal compound I-10-2, whose structural formula is as follows: Ⅰ-10-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-(4-bromo-3-fluorophenyl)-5-propyltetrahydropyran, and the final product Ⅰ-10-2 (15.4 g, yield 53%) is obtained, MS (m/z) (M+): 390.13.

Embodiment 11

This embodiment provides a liquid crystal compound I-14-1, whose structural formula is as follows: Ⅰ-14-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-(4-bromo-3-fluorophenyl)-5-ethyl-1,3-dioxacyclohexane, and the final product Ⅰ-14-1 (16.3 g, yield 52%) is obtained, MS (m/z) (M+): 378.09.

Embodiment 12

This embodiment provides a liquid crystal compound I-14-2, whose structural formula is as follows: Ⅰ-14-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 2-(4-bromo-3-fluorophenyl)-5-propyl-1,3-dioxacyclohexane, and the product Ⅰ-14-2 (17.2 g, yield 54%) is finally obtained, MS (m/z) (M+): 392.11.

Embodiment 13

This embodiment provides a liquid crystal compound I-19-1, whose structural formula is as follows: Ⅰ-19-1 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by p-ethylbromobenzene, and the final product Ⅰ-19-1 (19.7 g, yield 59%) is obtained, MS (m/z) (M+): 274.06.

Embodiment 14

This embodiment provides a liquid crystal compound I-19-2, whose structural formula is as follows: Ⅰ-19-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by p-propylbromobenzene, and the final product Ⅰ-19-2 (22 g, yield 61%) is obtained, MS (m/z) (M+): 288.08.

Embodiment 15

This embodiment provides a liquid crystal compound I-20-2, whose structural formula is as follows: Ⅰ-20-2 The synthetic route of the compound is as follows:

The specific synthesis method is the same as that of Compound Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by p-propyl-o-fluorobromobenzene, and the final product Ⅰ-20-2 (18.5 g, yield 46%) is obtained, MS (m/z) (M+): 306.07.

Embodiment 16

This embodiment provides a liquid crystal compound I-21-1, whose structural formula is as follows: Ⅰ-21-1 The synthetic route of this compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 4-ethyl-2,6-difluorobromobenzene, and the final product Ⅰ-21-1 (16.4 g, yield 38%) is obtained, MS (m/z) (M+): 310.04.

Embodiment 17

This embodiment provides a liquid crystal compound I-21-2, whose structural formula is as follows: Ⅰ-21-2 The synthetic route of this compound is as follows:

The specific synthesis method is the same as that of Example 1, except that 1-bromo-4-(4-ethylcyclohexyl)-2-fluorobenzene is replaced by 4-propyl-2,6-difluorobromobenzene, and the final product Ⅰ-21-2 (15.4 g, yield 36%) is obtained, MS (m/z) (M+): 324.06.

The performance parameters of the monomer are shown in Table 1:

Table 1 Single body performance parameters Compound Structural _K11 K ₂₂ K ₃₃ ∆ε γ ₁ Ⅰ-6-2 72.6 36.3 27.6 17.4 215.9 Ⅰ-8-2 39.2 19.6 26.3 26.3 159.9 Ⅰ-26-1 50.4 25.2 30.6 7.6 180.4 Ⅰ-27-1 45.6 22.8 28.5 16.3 156.8 Ⅰ-19-2 35.2 17.6 21.6 7.8 40.2 Ⅰ-20-2 22.4 11.2 16.3 18.3 35.3 Ⅰ-21-2 15.6 7.8 17.4 26.1 30.2 Ⅰ-23-2 25.4 17.7 16.8 12.9 38.6 Ⅰ-24-2 24.2 12.1 17.1 18.9 35.8 D1 24.2 14.3 12.2 7.0 39.2 D2 32.8 21.4 10.8 1.8 58.6 D3 15.6 11.2 13.2 18.3 34.2 D4 14.2 7.1 11.3 3.8 38.6

In order to explain the present invention more clearly, the present invention is further described below in conjunction with the preferred composition examples. Those skilled in the art should understand that the content described below is illustrative rather than restrictive, and should not be used to limit the scope of protection of the present invention.

In the present invention, the preparation methods are conventional methods unless otherwise specified, and the raw materials used can be obtained from public commercial channels unless otherwise specified. The percentages are all quality percentages, and the temperature is degrees Celsius (℃). The liquid crystal compound also becomes a liquid crystal monomer. The specific meanings and test conditions of other symbols are as follows: Cp represents the clearing point of the liquid crystal (℃), and is tested by the DSC quantitative method; SN represents the melting point of the liquid crystal from the crystalline state to the nematic phase (℃); △n represents the optical anisotropy, Δn= _ne - _no , where _no is the refractive index of ordinary light, and _ne is the refractive index of extraordinary light. The test conditions are 25±2℃, 589nm, and Abbe refractometer test; △ε represents the dielectric anisotropy, Δε= _ε∥ - _ε⊥ , where _ε∥ is the dielectric constant parallel to the molecular axis, ε _⊥ is the dielectric constant perpendicular to the molecular axis, and the test conditions are 25±0.5℃, 20 micron parallel box, INSTEC:ALCT-IR1 test; γ ₁ represents the rotational viscosity (mPa·s), and the test conditions are 25±0.5℃, 20 micron vertical box, INSTEC:ALCT-IR1 test; K ₁₁ is the splay elastic constant, K ₃₃ is the bending elastic constant, and K ₂₂ is the torsion elastic constant, and the test conditions are: 25±2℃, INSTEC:ALCT-IR1, 20 micron vertical box; Afterimage: The afterimage of the liquid crystal display device is to make the specified fixed pattern display in the display area for 1000 hours, and then visually evaluate the residual level of the inherent pattern when the full screen is evenly displayed, and the following 4 levels are used: ◎No residue□Very small amount of residue, which is acceptable△Residue, which is unacceptable×Residue, which is quite bad

The preparation method of the liquid crystal composition is as follows: each liquid crystal monomer is weighed according to a certain ratio and put into a stainless steel beaker, the stainless steel beaker containing each liquid crystal monomer is placed on a magnetic stirrer to heat and melt, and after most of the liquid crystal monomers in the stainless steel beaker are melted, a magnetic rotor is added to the stainless steel beaker, the mixture is stirred evenly, and the liquid crystal composition is obtained after cooling to room temperature.

The liquid crystal monomer structure of the embodiment of the present invention is represented by a code, and the code representation method of the liquid crystal ring structure, end group, and connecting group is shown in Table 2 and Table 3 below.

Table 2 Corresponding codes of ring structures Ring structure Corresponding code C P L G Gi Y U K A D Sa Sb W Sc

Table 3 Corresponding codes of terminal groups and linking groups Terminal groups and linking groups Corresponding code C _n H _2n+1 - n- C _n H _2n+1 O- nO- -CF ₃ -T -OCF ₃ -OT _-CF2O- -Q- _-CH2O- -O- -O- -B- -F -F -CN -CN -CH ₂ CH ₂ - -E- -CH=CH- -V- -COO- -Z- -CH=CH-C _n H _2n+1 -Vn Cp- Cpr- Cpr1-

For example: , its code is CC-Cp-V1; , whose code is P GP- Cpr1-2; , its code is CPP-3-2V1; , its code is CPU-3-F; , its code is CCP-V-OT; , its code is CPUQU-3-F; , its code is APUQU-3-F; , its code is DPU-3-F; , whose code is PW-3; , its code is PUW-3; , its code is AW-3.

Composition 1

Table 4 Formulation of liquid crystal composition 1 and corresponding properties Category Liquid crystal unit code Content (%) Ⅱ CC-3-V 49 Ⅱ CC-3-V1 4 Ⅴ P GP-2-F 6 Ⅴ P GP-3-F 6 VI CPP-3-1 5.5 VI CPP-3-2 1.5 III APUQU-2-F 5 III APUQU-3-F 5 III P GUQU-3-F 4.5 III P GUQU-4-F 5 Ⅰ Ⅰ-6-2 3.5 Ⅹ CC GVF 5

Composition 2

Table 5 Formulation of Liquid Crystal Composition 2 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅹ CCP-3-OT 6 Ⅹ CCP-5-OT 4 Ⅹ CCP G-3-F 3 VI CCP-V-1 12 Ⅱ CC-3-V 41.2 III P GUQU-3-F 4.5 III P GUQU-4-F 4.5 III P GUQU-5-F 4.5 Ⅸ-2 PP GU-Cp-F 0.5 VIII CPUP-3-OT 3.5 Ⅰ Ⅰ-6-2 4 Ⅸ-1 PUQU-3-F 4.8 Ⅺ CPPC-3-3 1.5 III P GUQU-Cp-F 2 VI CPP-3-2 3 VI CCP-3-O1 1

Composition 3

Table 6 Formulation of Liquid Crystal Composition 3 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅱ CC-3-V 32.5 Ⅹ CCPU-3-F 4 Ⅹ CCPU-2-F 4 Ⅹ CCPU-4-F 3 Ⅸ-1 CCQU-3-F 15 Ⅹ CPU-3-F 24.5 P GU-3-F 8 III P GUQU-4-F 4 Ⅰ Ⅰ-19-2 5

Composition D1

Table 7 Formulation of liquid crystal composition D1 and corresponding properties Category Liquid crystal unit code Content (%) Ⅱ CC-3-V 32.5 Ⅹ CCPU-3-F 4 Ⅹ CCPU-2-F 4 Ⅹ CCPU-4-F 3 Ⅸ-1 CCQU-3-F 15 Ⅹ CPU-3-F 24.5 P GU-3-F 8 III P GUQU-4-F 4 D1 5

Composition D2

Table 8 Formulation and corresponding properties of liquid crystal composition D2 Category Liquid crystal unit code Content (%) Ⅱ CC-3-V 32.5 Ⅹ CCPU-3-F 4 Ⅹ CCPU-2-F 4 Ⅹ CCPU-4-F 3 Ⅸ-1 CCQU-3-F 15 Ⅹ CPU-3-F 24.5 P GU-3-F 8 III P GUQU-4-F 4 D2 5

Composition 4

Table 9 Formulation of Liquid Crystal Composition 4 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅹ CCP-3-OT 8 Ⅹ CCP-5-OT 5 Ⅹ CCP G-3-F 6 Ⅱ CC-3-V 50 P GU-2-F 5 P GU-3-F 4.5 III CPUQU-Cp-F 5 III APUQU-Cp-F 3 Ⅸ-2 PP GU-Cp-F 0.5 VI CPP-1V-2 2 VI CPP-3-2V1 7 Ⅰ Ⅰ-20-2 4

Composition D3

Table 10 Formulation and corresponding properties of liquid crystal composition D3 Category Liquid crystal unit code Content (%) Ⅹ CCP-3-OT 8 Ⅹ CCP-5-OT 5 Ⅹ CCP G-3-F 6 Ⅱ CC-3-V 50 P GU-2-F 5 P GU-3-F 4.5 III CPUQU-Cp-F 5 III APUQU-Cp-F 3 Ⅸ-2 PP GU-Cp-F 0.5 VI CPP-1V-2 2 VI CPP-3-2V1 7 D3 4

Composition 5

Table 11 Formulation of Liquid Crystal Composition 5 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅱ CC-3-V 47 Ⅱ CC-3-V1 5 III P GUQU-3-F 6 III P GUQU-4-F 3 Ⅰ Ⅰ-20-2 3 Ⅹ CC GVF 5 Ⅴ P GP-2-2V 7 VII PP-1-2V1 5 III APUQU-3-F 7 III P GUQK-3-F 4 Ⅴ P GP-2-F 4 Ⅰ-24-2 4

Composition 6

Table 12 Formulation of Liquid Crystal Composition 6 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅰ Ⅰ-19-2 4.5 Ⅰ Ⅰ-24-2 5.5 Ⅱ CC-3-V 45 Ⅱ CC-3-2V1 7 III P GUQU-3-F 5.5 III CPUQU-3-F 5 III DPUQU-4-F 4 IV DP GU-4-F 5 VI CLP-V-1 5 VII PP-1-2V1 8 VI CCP-V-1 5 Ⅸ-2 PP GU-3-F 0.5

Composition 7

Table 13 Formulation of Liquid Crystal Composition 7 and its corresponding properties Category Liquid crystal unit code Content (%) Ⅰ Ⅰ-20-2 3 Ⅱ CC-3-V 45 Ⅱ CC-3-V1 7 Ⅱ CC-3-2V1 5 III P GUQU-3-F 4.5 III D GUQU-3-F 5 Ⅴ P GP-2-2V 5 Ⅴ P GP-1-2V 6.5 VI CPP-3-1 6 VII PP-1-2V1 7 IV DP GU-4-F 1.5 Ⅸ-2 PP GU-Cp-F 0.5 Ⅰ Ⅰ-21-2 4

Composition D4

Table 14 Formulation and corresponding properties of liquid crystal composition D4 Category Liquid crystal unit code Content (%) D2 3 Ⅱ CC-3-V 45 Ⅱ CC-3-V1 7 Ⅱ CC-3-2V1 5 III P GUQU-3-F 4.5 III D GUQU-3-F 5 Ⅴ P GP-2-2V 5 Ⅴ P GP-1-2V 6.5 VI CPP-3-1 6 VII PP-1-2V1 7 IV DP GU-4-F 1.5 Ⅸ-2 PP GU-Cp-F 0.5 D4 4

Investigation of low temperature solubility of liquid crystal compositions

Compositions 1-7 and compositions D1-D4 used as comparative examples were placed in stainless steel beakers, respectively. The stainless steel beakers were placed on a magnetic stirrer to heat and melt. After the liquid crystal monomer in the stainless steel beaker was melted, a magnetic rotor was added to the stainless steel beaker, and the mixture was stirred evenly. After cooling to room temperature, the mixture was filtered with a 0.45 um PTFE filter. The prepared liquid crystal composition was then transferred to a penicillin bottle (bulk), with about 2 ml of liquid crystal in each bottle, and placed at -10 ℃, -20 ℃, -30 ℃, and 40 ℃. ℃ constant temperature glove box, observe the bulk bottle every day to see if there is precipitation or smectic crystal, and continue observing for 30 days (30d). The later the crystallization occurs, the better the low-temperature solubility of the liquid crystal composition.

Table 15 Composition 1 Composition 2 Composition 3 Composition D1 Composition D2 Composition 4 Composition D3 Composition 5 Composition 6 Composition 7 Composition D4 Cp 78.8 100.9 81.2 79.5 80.3 91.2 90.1 73.5 83.4 79.6 72.1 Δn 0.116 0.118 0.115 0.114 0.113 0.107 0.105 0.124 0.123 0.126 0.125 Δε 6.8 7.3 8.9 8.9 8.6 5.5 5.1 6.8 5.9 4.2 4.2 γ ₁ 49.3 69.8 56.7 56.6 61.2 55.3 54.6 43.2 45 42.3 42.1 _K11 13.2 16 12.8 11.3 12.3 13.5 12.1 12.8 13.5 13.9 12.3 K ₃₃ 13.7 18.1 12.9 11.8 11.9 12.9 11.6 13.1 14.1 14.2 13.1 γ ₁ /K 3.73 4.36 4.43 5.01 4.98 4.10 4.51 3.38 3.33 3.04 3.42 -10 ℃ No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation -20 ℃ No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation Crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation Crystal precipitation -30 ℃ No crystal precipitation No crystal precipitation No crystal precipitation Crystal precipitation Crystal precipitation No crystal precipitation Crystal precipitation No crystal precipitation No crystal precipitation No crystal precipitation Crystal precipitation Remains □ □ ◎ △ × ◎ × ◎ ◎ ◎ △

From the above experimental data, it can be seen that the liquid crystal compound of the present invention has a large dielectric anisotropy △ε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity γ1 and a large elastic constant K. The liquid crystal composition of the present invention has a large dielectric anisotropy △ε, a high elastic constant K, good low-temperature miscibility, a small rotational viscosity γ1 and a large elastic constant K, and can be used to develop a liquid crystal display element or liquid crystal display with a faster response speed and can effectively improve afterimages.

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 ordinary technical personnel in the relevant field, other different forms of changes or modifications can be made based on the above description. It is impossible to list all the implementation methods here. All obvious changes or modifications derived from the technical solution of the present invention are still within the scope of protection of the present invention.

Figure 1 shows the MS mass spectrum of the compound shown in I-6-2.

Claims (14)

A liquid crystal compound selected from the group consisting of compounds represented by the following formulas I-1 to I-27, Ⅰ-1 Ⅰ-2 Ⅰ-3 Ⅰ-4 Ⅰ-5 Ⅰ-6 Ⅰ-7 Ⅰ-8 Ⅰ-9 Ⅰ-10 Ⅰ-11 Ⅰ-12 Ⅰ-13 Ⅰ-14 Ⅰ-15 I-16 Ⅰ-17 Ⅰ-18 Ⅰ-19 Ⅰ-20 Ⅰ-21 Ⅰ-22 I-23 Ⅰ-24 Ⅰ-25 I-26 Ⅰ-27 Wherein, R represents an alkyl group having 1 to 15 carbon atoms. The liquid crystal compound as described in claim 1, wherein the compounds represented by formulas I-1 to I-27 are selected from any one or any combination of the compounds represented by the following formulas I-1-1 to I-27-1, Ⅰ-1-1 Ⅰ-1-2 Ⅰ-2-1 Ⅰ-2-2 Ⅰ-3-1 Ⅰ-3-2 Ⅰ-4-1 Ⅰ-4-2 Ⅰ-5-1 Ⅰ-5-2 Ⅰ-6-1 Ⅰ-6-2 Ⅰ-7-1 Ⅰ-7-2 Ⅰ-8-1 Ⅰ-8-2 Ⅰ-9-1 Ⅰ-9-2 Ⅰ-10-1 Ⅰ-10-2 Ⅰ-11-1 Ⅰ-11-2 Ⅰ-12-1 Ⅰ-12-2 Ⅰ-13-1 Ⅰ-13-2 Ⅰ-14-1 Ⅰ-14-2 Ⅰ-15-1 Ⅰ-15-2 Ⅰ-16-1 Ⅰ-16-2 Ⅰ-17-1 Ⅰ-17-2 Ⅰ-18-1 Ⅰ-18-2 Ⅰ-19-1 Ⅰ-19-2 Ⅰ-20-1 Ⅰ-20-2 Ⅰ-21-1 Ⅰ-21-2 Ⅰ-22-1 Ⅰ-22-2 Ⅰ-23-1 Ⅰ-23-2 Ⅰ-24-1 Ⅰ-24-2 Ⅰ-25-1 Ⅰ-25-2 Ⅰ-26-1 Ⅰ-27-1. A liquid crystal composition comprising one or more liquid crystal compounds as described in any one of claims 1 to 2. The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula II, Ⅱ Wherein, R ₃ represents an alkyl group having 1 to 10 carbon atoms; R ₄ represents an alkenyl group having 2 to 10 carbon atoms. The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula III, III wherein, R ₅ represents a chain alkyl group having 1 to 15 carbon atoms, and one or more non-adjacent -CH ₂ - in R ₅ are optionally substituted by cyclopentylene or cyclopropylene; Xa represents H or CH ₃ ; Each independently expresses , , , or . The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula IV, IV wherein R ₆ represents a chain alkyl group having 1 to 10 carbon atoms; express , or . The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula V, Ⅴ wherein R ₇ represents an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, F, CF ₃ or OCF ₃ ; R ₈ represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms. The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula VI, VI wherein R ₉ and R ₁₀ each independently represent an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms; express , or . The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula VII, VII wherein, Ra represents a chain alkyl group having 1 to 15 carbon atoms; Rb represents a chain alkyl group having 1 to 15 carbon atoms, a chain alkoxy group having 1 to 15 carbon atoms, or a chain alkenyl group having 2 to 15 carbon atoms; express or . The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula VIII, VIII wherein Rc represents a chain alkyl group having 1 to 15 carbon atoms; X ₁ , X ₂ , and X ₃ each independently represent H or F, and at least one of X ₁ , X ₂ , and X ₃ represents F. The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula IX-1 or IX-2, Ⅸ-1 IX-2 wherein Rd and Re each independently represent a chain alkyl group having 1 to 15 carbon atoms, wherein one or more non-adjacent -CH ₂ - in Rd and Re are optionally substituted by cyclopentylene or cyclopropylene; , Each independently expresses , or . The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula X, Ⅹ wherein, Rf represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms; _X4 represents H or F; _X5 represents F or _OCF3 ; a represents 1 or 2; express or , and when a represents 2, the two Choose Same or Different. The liquid crystal composition as described in claim 3 further comprises one or more compounds represented by formula XI, Ⅺ wherein, Rg and Rh each independently represent a chain alkyl group having 1 to 15 carbon atoms; Z represents a single bond or -COO-; express or . A liquid crystal display element or a liquid crystal display comprises the liquid crystal compound described in any one of claims 1 to 2 or the liquid crystal composition described in any one of claims 3 to 13, wherein the liquid crystal display element or the liquid crystal display is an active matrix display element or display.