Liquid crystal compound, liquid crystal composition thereof, and liquid crystal display device

Abstract

The present invention provides a liquid crystal compound of general formula F, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition. The liquid crystal compound of the present invention has a high clearing point, a large optical anisotropy, and an equivalent or higher absolute value of dielectric anisotropy while maintaining a suitable rotational viscosity, so that the liquid crystal composition containing the compound of general formula F of the present invention has a large optical anisotropy, a small rotational viscosity, a high VHR(UV) and a long low-temperature storage time while maintaining a suitable clearing point, a suitable absolute value of dielectric anisotropy, and a suitable VHR(initial), and the liquid crystal display device containing the liquid crystal composition of the present invention has a high contrast, a fast response speed, high reliability and high low-temperature storage stability. [Case 1] TIFF2024542038000219.tif26170

Description

[Technical Field]

[0001] The present invention relates to the field of liquid crystals, and more particularly to a liquid crystal compound, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition. [Background technology]

[0002] Liquid crystal display devices can be used in a variety of applications, including watches and calculators, measuring instruments, automotive panels, word processors, computers, printers, and televisions. Depending on the display mode, liquid crystal display devices can be divided into various types, such as phase change (PC), twisted nematic (TN), super twisted nematic (STN), electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), and vertical alignment (VA). Depending on the driving method, liquid crystal display devices can be divided into passive matrix (PM) and active matrix (AM) types. PM devices can be further divided into static and multiplex types. AMs are divided into types such as TFT (thin film transistor) and MIM (metal insulator metal). TFT types include amorphous silicon and polycrystalline silicon. The latter are divided into high-temperature and low-temperature types depending on the manufacturing process. Depending on the type of light source, LCD devices can be divided into reflective types that use natural light, transmissive types that use backlight, and transflective types that use both natural light and backlight.

[0003] A liquid crystal display element contains a liquid crystal composition having a nematic phase, and the liquid crystal composition has appropriate characteristics. By improving the characteristics of the liquid crystal composition, an AM element with good characteristics can be obtained. The relationship between the characteristics of the liquid crystal composition and the characteristics of the AM element is summarized in Table 1 below.

[0004] [Table 1]

[0005] In the application of LCD devices, the impact of contrast on visual effects is very important. Generally, the higher the contrast, the clearer and more striking the image, and the more vivid and beautiful the colors, while the lower the contrast, the more dim the overall screen. High contrast contributes greatly to image clarity, detail expression, and gradation expression. High-contrast products have advantages in black-and-white contrast, clarity, completeness, etc. Contrast also has a significant impact on the display effect of dynamic video. Because the light-dark transitions in dynamic images are rapid, the higher the contrast, the easier it is for the human eye to distinguish these transitions.

[0006] As the resolution of LCD displays improves, 4K and 8K resolution LCD displays are gradually emerging, requiring LCD panels with small aperture ratios and high light transmittance. Negative liquid crystal compositions have high light transmittance, especially in PSA and NFFS modes. However, the structure of negative liquid crystals determines their high rotational viscosity and low voltage holding ratio. To overcome the shortcomings of conventional negative liquid crystals and provide liquid crystal compositions that meet market demand, there is an urgent need to develop negative liquid crystal compounds with low rotational viscosity and high voltage holding ratio.

[0007] Chinese Patent Application CN1942461A and German Patent Application DE10101022A1 disclose liquid crystal compounds that solve the above problems to some extent, while Chinese Patent Application CN107973766A uses ring substitution on the terminal group structure of this type of compound based on prior art. However, the currently disclosed compounds have problems such as small absolute value of dielectric anisotropy, high rotational viscosity, and poor low-temperature compatibility. More serious is the poor UV stability of benzofuran and benzothiophene compounds. As is well known, the manufacturing process of LCD panels requires exposure to a certain amount of UV light. Typically, the irradiance of ultraviolet light with a wavelength of 365 nm is about 6000-1000 MJ. Conventional benzofuran and benzothiophene compounds have low VHR(UV) after UV exposure, which reduces display reliability and causes image retention.

[0008] Therefore, how to obtain a liquid crystal compound and a liquid crystal composition containing the same that can solve or partially solve the above problems remains a problem to be solved in the art. Summary of the Invention [Problem to be solved by the invention]

[0009] In order to overcome the drawbacks of the prior art, the present invention aims to provide a liquid crystal compound having a high clearing point, a large optical anisotropy, and an equivalent or higher absolute value of dielectric anisotropy while maintaining an appropriate rotational viscosity.

[0010] Furthermore, the present invention aims to provide a liquid crystal composition containing the above liquid crystal compound, which has large optical anisotropy, small rotational viscosity, high VHR(UV), and long low-temperature storage time while maintaining a suitable clearing point, a suitable absolute value of dielectric anisotropy, and a suitable VHR(initial).

[0011] Another object of the present invention is to provide a liquid crystal display device containing the liquid crystal composition. [Means for solving the problem]

[0012] In order to achieve the above object of the invention, the present invention provides a liquid crystal compound represented by general formula F: [ka] During the ceremony, R F1 is -H, halogen, a straight or branched chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; [ka] [ka] or [ka] wherein one or two or more non-adjacent —CH— groups in the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by —C≡C—, —O—, —CO—, —CO-O— or —O-CO—, and one or more —H groups in the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by —F or —Cl, ring [ka] and ring [ka] are each independently [ka] or [ka] represents [ka] and [ka] one or more -CH2- in the ring may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds; [ka] and [ka] one or more -H in the ring may each independently be replaced by -CN, -F, or -Cl, and one or more -CH= in the ring may be replaced by -N=; X F represents -O-, -S- or -CO-; L F1 and L F2 each independently represents -H, -F, -Cl, -CF3, or -OCF3; Z F1 and Z F2 each independently represents a single bond, -O-, -CO-O-, -O-CO-, -CHO-, -OCH-, -CH=CH-, -C≡C-, -CHCH-, -CFCF-, -(CH)-, -CFO-, or -OCF-, n F1 and n F2 each independently represents 0, 1 or 2; n F1 If represents 2, the ring [ka] may be the same or different, and n F2 If represents 2, the ring [ka] may be the same or different, and Z F2 may be the same or different, and n F3 represents an integer of 0 to 4.

[0013] In some embodiments of the present invention, preferably, LF1 and L F2 each independently represents -F or -Cl.

[0014] In some embodiments of the present invention, compounds of general formula F are [ka] [ka] is selected from the group consisting of compounds During the ceremony, X F1 and X F2 each independently represents -CH2- or -O-.

[0015] In some embodiments of the present invention, in order to obtain a large absolute value of dielectric anisotropy while maintaining a suitable clearing point, a suitable optical anisotropy, and a suitable rotational viscosity, F Preferably, represents -S-.

[0016] In some embodiments of the present invention, preferably, n F3 represents 0 or 1, and more preferably, n F3 represents 0.

[0017] In some embodiments of the present invention, preferably, Z F1 and Z F2 each independently represents a single bond, -CH2O- or -OCH2-, and more preferably Z F1 and Z F2 Each of these represents a single bond.

[0018] In some embodiments of the present invention, n F1 and n F2 At least one of n represents 0, and more preferably F1 and n F2 Both represent 0.

[0019] In some embodiments of the present invention, preferably, R F1represents a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms, and more preferably R F1 represents a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms.

[0020] In some embodiments of the present invention, in compounds of general formula F-1, compounds of general formula F-2, compounds of general formula F-3, compounds of general formula F-4, compounds of general formula F-5, compounds of general formula F-6, compounds of general formula F-26, and compounds of general formula F-27, R F1 represents a straight or branched chain alkoxy group containing 1 to 7 carbon atoms.

[0021] In some embodiments of the present invention, the compound of general formula F-1 is [ka] The compound is selected from the group consisting of:

[0022] In some embodiments of the present invention, the compound of general formula F-2 is [ka] The compound is selected from the group consisting of:

[0023] In some embodiments of the present invention, compounds of general formula F-5 are [ka] The compound is selected from the group consisting of:

[0024] In some embodiments of the present invention, compounds of general formula F-6 are [ka] The compound is selected from the group consisting of:

[0025] In some embodiments of the present invention, compounds of general formula F-9 are [ka] The compound is selected from the group consisting of:

[0026] The liquid crystal compound of the present invention has a large absolute value of dielectric anisotropy and is particularly applicable to VA-TFT, IPS, or FFS display devices. The absolute value of the dielectric anisotropy is 10 or more (e.g., 10.5), preferably 12 or more (e.g., 13 or 14), and preferably 15 or more (e.g., 15.8, 16, or 16.4), and is applicable to liquid crystal compositions that have high requirements for the absolute value of dielectric anisotropy. Furthermore, when applied to liquid crystal compositions, such compounds of the present invention have high miscibility, high low-temperature storage stability, low rotational viscosity, and high VHR(UV), and have high reliability even after UV treatment.

[0027] In another aspect, the present invention provides a liquid crystal composition comprising at least one liquid crystal compound of general formula F above.

[0028] In some embodiments of the present invention, it is preferable to adjust the content of the compound of general formula F so that the liquid crystal composition of the present invention has large optical anisotropy, small rotational viscosity, high VHR(UV) and long low-temperature storage time while maintaining a suitable clearing point, a suitable absolute value of dielectric anisotropy and a suitable VHR(initial).

[0029] In some embodiments of the present invention, the weight percentage of the compound of general formula F in the liquid crystal composition is 0.1% to 30% (all values ​​inclusive), for example, 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, or any range of values ​​between any two thereof.

[0030] In some embodiments of the present invention, in order to obtain large optical anisotropy, small rotational viscosity, high VHR(UV) and long low-temperature storage time, the liquid crystal composition preferably contains at least two (e.g., two, three) compounds of general formula F.

[0031] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of general formula N, [ka] During the ceremony, R N1 and R N2 are each independently a straight-chain or branched-chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; [ka] or [ka] wherein one or two or more non-adjacent —CH— groups in the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O—, or —O—CO—; ring [ka] and ring [ka] are each independently [ka] or [ka] represents [ka] one or more -CH2- in the ring may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds; [ka] one or more -H in the ring may each independently be replaced by -F, -Cl, or -CN, and one or more -CH= in the ring may be replaced by -N=; Z N1 and Z N2 each independently represents a single bond, -CO-O-, -O-CO-, -CHO-, -OCH-, -CH=CH-, -C≡C-, -CHCH-, -CFCF-, -(CH)-, -CFO-, or -OCF-, L N1 and L N2 each independently represents -H, an alkyl group having 1 to 3 carbon atoms, or a halogen atom, and n N1 represents 0, 1, 2 or 3, and n N2 represents 0 or 1, and 0≦n N1 +n N2 ≦3, and n N1 = 2 or 3, the ring [ka] may be the same or different, and Z N1 may be the same or different.

[0032] In some embodiments of the present invention, L N1 and L N2 Both represent -H.

[0033] In some embodiments of the present invention, compounds of general formula N are [ka] [ka] [ka] The compound is selected from the group consisting of:

[0034] In some embodiments of the present invention, preferably, R N1 and R N2 each independently represents a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms, and more preferably R N1 and R N2 each independently represents a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms.

[0035] In some embodiments of the present invention, preferably, the compound of general formula N is selected from the group consisting of compounds of general formula N-1, compounds of general formula N-2, compounds of general formula N-3, compounds of general formula N-9, compounds of general formula N-12, compounds of general formula N-13, compounds of general formula N-19, compounds of general formula N-21, compounds of general formula N-24, compounds of general formula N-27, and compounds of general formula N-30.

[0036] In some embodiments of the present invention, in order to obtain a large optical anisotropy, a high clearing point, a small rotational viscosity, a suitable VHR(initial), a high VHR(UV) and a long low-temperature storage time, the compound of general formula N is preferably selected from the group consisting of compounds of general formula N-2, compounds of general formula N-3, compounds of general formula N-9, compounds of general formula N-12 and compounds of general formula N-13.

[0037] In some embodiments of the present invention, in order to obtain large optical anisotropy, small rotational viscosity, high VHR(UV) and long low-temperature storage time, the compound of general formula N is preferably selected from the group consisting of compounds of general formula N-1, compounds of general formula N-19, compounds of general formula N-21, compounds of general formula N-24, compounds of general formula N-27 and compounds of general formula N-30.

[0038] In some embodiments of the present invention, it is preferable to adjust the content of the compound of general formula N so that the liquid crystal composition of the present invention has a suitable clearing point, a suitable absolute value of dielectric anisotropy, a suitable VHR(initial), a large optical anisotropy, a small rotational viscosity, a high VHR(UV), and a long low-temperature storage time.

[0039] In some embodiments of the present invention, the weight percentage of the compound of general formula N in the liquid crystal composition is 0.1% to 70% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 37%, 38%, 40%, 42%, 44%, 46%, 48%, 49%, 50%, 52%, 53%, 54%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 64%, 66%, 68%, 70%, or any range of values ​​between any two thereof.

[0040] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of general formula M, [ka] During the ceremony, R M1 and R M2 are each independently a straight-chain or branched-chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; [ka] [ka] wherein one or two or more non-adjacent —CH— groups in the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O—, or —O—CO—; ring [ka] ,ring [ka] and ring [ka] are each independently [ka] or [ka] represents [ka] one or more -CH2- in the ring may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds; [ka] wherein at most one -H may be replaced by halogen; Z M1 and Z M2 each independently represents a single bond, -CO-O-, -O-CO-, -CHO-, -OCH-, -C≡C-, -CH=CH-, -CHCH- or -(CH)-; n M represents 0, 1 or 2, n M If =2, then the ring [ka] may be the same or different, and Z M2 may be the same or different.

[0041] In some embodiments of the present invention, preferably, R M1 and R M2 each independently represents a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms, and more preferably R M1 and R M2 each independently represents a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms.

[0042] In some embodiments of the present invention, preferably, R M1 and R M2 each independently represents a linear alkenyl group containing 2 to 8 carbon atoms, and more preferably, R M1 and R M2 each independently represents a linear alkenyl group containing 2 to 5 carbon atoms.

[0043] In some embodiments of the present invention, preferably, R M1 and R M2 One of them is a straight-chain alkenyl group containing 2 to 5 carbon atoms, and the other is a straight-chain alkyl group containing 1 to 5 carbon atoms.

[0044] In some embodiments of the present invention, preferably, R M1 and R M2 each independently represents a linear alkoxy group containing 1 to 8 carbon atoms, and more preferably, R M1 and R M2 each independently represents a linear alkoxy group containing 1 to 5 carbon atoms.

[0045] In some embodiments of the present invention, preferably, R M1 and R M2 One of them is a straight-chain alkoxy group containing 1 to 5 carbon atoms, and the other is a straight-chain alkyl group containing 1 to 5 carbon atoms.

[0046] In some embodiments of the present invention, when reliability is important, it is preferable to M1 and R M2 are all alkyl groups, and when it is important to reduce the volatility of the compound, it is preferable to use R M1 and R M2 are both alkoxy groups, and when a reduction in viscosity is important, R M1 and R M2 At least one of the groups is an alkenyl group.

[0047] As used herein, the term "comprising 1 to r carbon atoms" (where r is an integer greater than 1) may include any integer between 1 and r (inclusive) carbon atoms, such as including 2 carbon atoms, including (r-1) carbon atoms, or including r carbon atoms. For example, "comprising 1 to 12 carbon atoms" may include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0048] As used herein, the term "an integer between y1 and y2" may be any integer within this range, including the endpoints y1 and y2. For example, an "integer between 0 and 12" may be, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0049] The alkenyl group of the present invention is preferably selected from groups represented by any one of formulas (V1) to (V9), and particularly preferably selected from groups represented by formula (V1), formula (V2), formula (V8) or formula (V9). The groups represented by formulas (V1) to (V9) are: [ka] and In the formula, * represents the bonding site in the bonded ring structure.

[0050] The alkenyloxy group of the present invention is preferably selected from groups represented by any one of formulas (OV1) to (OV9), and particularly preferably selected from groups represented by formula (OV1), formula (OV2), formula (OV8) or formula (OV9). The groups represented by formulas (OV1) to (OV9) are [ka] and In the formula, * represents the bonding site in the bonded ring structure.

[0051] In some embodiments of the present invention, compounds of general formula M are [ka] [ka] The compound is selected from the group consisting of:

[0052] In some embodiments of the present invention, in order to obtain a large optical anisotropy, a suitable clearing point, a small rotational viscosity, a suitable VHR(initial), a high VHR(UV) and a long low-temperature storage time, the compound of general formula M is preferably selected from the group consisting of compounds of general formula M-1, compounds of general formula M-4, compounds of general formula M-11 and compounds of general formula M-13.

[0053] In some embodiments of the present invention, the content of the compound of general formula M needs to be appropriately adjusted depending on required performance such as low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, image sticking, and dielectric anisotropy.

[0054] Regarding the content of the compound of general formula M, if it is necessary to maintain a low viscosity and a short response time of the liquid crystal composition of the present invention, it is preferable to set the lower limit high and the upper limit high. Furthermore, if it is necessary to maintain a high clearing point and good temperature stability of the liquid crystal composition of the present invention, it is preferable to set the lower limit high and the upper limit high. In order to maintain a low driving voltage and increase the absolute value of the dielectric anisotropy, it is preferable to set the lower limit low and the upper limit low.

[0055] In some embodiments of the present invention, it is preferable to adjust the content of the compound of general formula M so that the liquid crystal composition of the present invention has a suitable clearing point, a suitable absolute value of dielectric anisotropy, a suitable VHR(initial), a large optical anisotropy, a small rotational viscosity, a high VHR(UV), and a long low-temperature storage time.

[0056] In some embodiments of the present invention, the weight percentage of the compound of general formula M in the liquid crystal composition is 0.1% to 70% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 37%, 38%, 40%, 42%, 44%, 46%, 47%, 48%, 49%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 70%, or any range of values ​​between any two thereof.

[0057] In some embodiments of the present invention, in order to apply the liquid crystal composition of the present invention to a high-transmittance liquid crystal display, the liquid crystal composition of the present invention further comprises at least one compound selected from the group consisting of compounds of general formula A-1 and general formula A-2. [ka] During the ceremony, R A1 and R A2 are each independently a straight-chain or branched-chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; [ka] or [ka] wherein one or two or more non-adjacent -CH2- groups in the linear or branched alkyl group containing 1 to 12 carbon atoms may be each independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; [ka] or [ka] one or more -H in each independently may be replaced by -F or -Cl; ring [ka] ,ring [ka] ring [ka] and ring [ka] are each independently [ka] or [ka] represents [ka] and [ka] one or more -CH2- in the ring may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds; [ka] and [ka] one or more -H in the ring may each independently be replaced by -F, -Cl, or -CN, and one or more -CH= in the ring may be replaced by -N=; Z A11 , Z A21 and Z A22 each independently represents a single bond, -CH2CH2-, -CF2CF2-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -CF=CF-, -CHO- or -OCH2-, L A11 , L A12 , L A13 , L A21 and L A22 each independently represents -H, an alkyl group containing 1 to 3 carbon atoms, or a halogen; X A1 and X A2 each independently represents a halogen, a linear or branched halogenated alkyl group or halogenated alkoxy group containing 1 to 5 carbon atoms, or a linear or branched halogenated alkenyl group or halogenated alkenyloxy group containing 2 to 5 carbon atoms; n A11 represents 0, 1, 2 or 3, and n A11 = 2 or 3, the ring [ka] may be the same or different, and Z A11 may be the same or different, n A12 represents 1 or 2, and n A12 If =2, then the ring [ka] may be the same or different, and n A2 represents 0, 1, 2 or 3, and n A2 = 2 or 3, the ring [ka] may be the same or different, and Z A21 may be the same or different.

[0058] In some embodiments of the present invention, the compound of general formula A-1 is [ka] [ka] [ka] is selected from the group consisting of compounds During the ceremony, R A1 is a linear or branched alkyl group containing 1 to 8 carbon atoms; [ka] or [ka] wherein one or two or more non-adjacent -CH2- groups in a straight or branched alkyl group containing 1 to 8 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H groups in these groups may each independently be replaced by -F or -Cl; R v and R w each independently represents -CH2- or -O-; L A11 , L A12, L A11 ', L A12 ′, L A14 , L A15 and L A16 each independently represents -H or -F; L A13 and L A13 Each ' independently represents -H or -CH; X A1 represents -F, -CF3 or -OCF3, and v and w each independently represent 0 or 1.

[0059] In some embodiments of the present invention, the weight percentage of the compound of general formula A-1 in the liquid crystal composition is 0.1% to 50% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, or a range of values ​​between any two thereof.

[0060] Regarding the preferred content of the compound of general formula A-1, when the viscosity of the liquid crystal composition of the present invention is to be kept low and the response speed is to be kept high, it is preferable that the lower limit be slightly lower and the upper limit be slightly lower. Furthermore, when the clearing point of the liquid crystal composition of the present invention is to be kept high and the temperature stability is to be kept high, it is preferable that the lower limit be slightly lower and the upper limit be slightly lower. Furthermore, when the driving voltage is to be kept low and the absolute value of the dielectric anisotropy is to be increased, it is preferable that the lower limit be slightly higher and the upper limit be slightly higher.

[0061] In some embodiments of the present invention, the compound of general formula A-2 is [ka] [ka] is selected from the group consisting of compounds During the ceremony, R A2 represents a straight-chain or branched-chain alkyl group containing 1 to 8 carbon atoms, in which one or two or more non-adjacent —CH— groups in the straight-chain or branched-chain alkyl group containing 1 to 8 carbon atoms may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO-O— or —O-CO—, and one or more —H groups in these groups may each independently be replaced by —F or —Cl, L A21 , L A22 , L A23 , L A24 and L A25 each independently represents -H or -F, and X A2 represents -F, -CF3, -OCF3 or -CH2CH2CH=CF2.

[0062] In some embodiments of the present invention, the weight percentage of the compound of general formula A-2 in the liquid crystal composition is 0.1% to 50% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, or a range of values ​​between any two thereof.

[0063] Regarding the preferred content of the compound of general formula A-2, when the viscosity of the liquid crystal composition of the present invention is to be kept low and the response speed is to be kept high, the lower limit is preferably slightly lower and the upper limit is preferably slightly lower. Furthermore, when the clearing point of the liquid crystal composition of the present invention is to be kept high and the temperature stability is to be kept high, the lower limit is preferably slightly lower and the upper limit is preferably slightly lower. Furthermore, when the driving voltage is to be kept low and the absolute value of the dielectric anisotropy is to be increased, the lower limit is preferably slightly higher and the upper limit is preferably slightly higher.

[0064] In some embodiments of the present invention, the weight percentage of the compound selected from the group consisting of compounds of general formula A-1 and general formula A-2 in the liquid crystal composition is 0.1% to 60% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, or a range of values ​​between any two thereof.

[0065] In some embodiments of the present invention, the liquid crystal composition further comprises at least one polymerizable compound of the general formula RM, [ka] During the ceremony, R1 is -H, halogen, -CN, -Sp2-P2, or a straight or branched chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; [ka] or [ka] a linear or branched alkyl group containing 1 to 12 carbon atoms; [ka] or [ka] in which one or two or more non-adjacent -CH2- groups may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-; and one or more -H groups may each independently be replaced by -F or -Cl; ring [ka] and ring [ka] are each independently [ka] or [ka] represents [ka] and [ka] one or more -CH2- in the ring may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds; [ka] and [ka] wherein one or more -H are each independently -F, -Cl, -CN, -Sp3-P3, a halogenated or non-halogenated straight-chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms, a halogenated or non-halogenated straight-chain alkoxy group containing 1 to 11 carbon atoms, [ka] or [ka] and one or more -CH= in the ring may be replaced by -N=; ring [ka] teeth, [ka] or [ka] represents [ka] or [ka] wherein one or more -H are each independently -F, -Cl, -CN, -Sp3-P3, a halogenated or non-halogenated straight-chain alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms, a halogenated or non-halogenated straight-chain alkoxy group containing 1 to 11 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11) carbon atoms, [ka] or [ka] and one or more -CH= in the ring may be replaced by -N=; P1, P2, and P3 each independently represent a polymerizable group; Sp1, Sp2, and Sp3 each independently represent a spacer group or a single bond; Z1 and Z2 each independently represent -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CHO-, -OCH-, -CHS-, -SCH-, -CFO-, -OCF-, -CFS-, -SCF-, or -(CH) d -, -CF2CH2-, -CH2CF2-, -(CF2) d -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2CH2-CO-O-, -O-CO-CH2CH2-, -CHR 1-, -CR 1 R 2 - or a single bond, R 1 and R 2 each independently represents a linear or branched alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms; d represents an integer of 1 to 4; X0 represents -O-, -S-, -CO-, -CF2-, -NH-, or -NF-; a represents 0, 1 or 2, b represents 0 or 1, and when a represents 2, the ring [ka] may be the same or different, and Z1 may be the same or different.

[0066] In some embodiments of the invention, compounds of the general formula RM are [ka] [ka] [ka] [ka] [ka] is selected from the group consisting of compounds During the ceremony, X1~X 10 and X 12 are each independently -F, -Cl, -Sp3-P3, a linear alkyl or alkoxy group containing 1 to 5 carbon atoms, [ka] or [ka] Represents.

[0067] Polymerizable groups according to the present invention are groups adapted for polymerization reactions (e.g. free radical or ionic polymerization, addition polymerization or condensation polymerization) or for addition or condensation in the polymer backbone. For chain polymerization, polymerizable groups containing -CH=CH- or -C≡C- are particularly preferred, and for ring-opening polymerization, for example, oxetanyl or epoxy groups are particularly preferred.

[0068] In some embodiments of the present invention, the polymerizable groups P1, P2, and P3 are each independently: [ka] or —SH, and preferably, the polymerizable groups P1, P2 and P3 each independently represent [ka] or —SH, and more preferably, the polymerizable groups P1, P2 and P3 each independently represent [ka] or [ka] Represents.

[0069] As used herein, the term "spacer group" is known to those skilled in the art and described in the literature (e.g., Pure Appl. Chem. 2001, 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368). As used herein, the term "spacer group" refers to a flexible group that connects a mesogenic group and a polymerizable group in a polymerizable compound. Typical spacer groups include, for example, -(CH)p1-, -(CH2CHO)q1-CH2CH2-, -(CH2CH2S)q1-CH2CH2-, -(CH2CH2NH)q1-CH2CH2-, -CR 0 R 00 -(CH2)p1 -or-(SiR 0 R 00 -O)p1-, where p1 represents an integer of 1 to 12, q1 represents an integer of 1 to 3, and R 0 and R 00 are each independently -H, a linear or branched alkyl group containing 1 to 12 carbon atoms, or a cyclic alkyl group containing 3 to 12 carbon atoms. Particularly preferred spacer groups are -(CH2)p1-, -(CH2)p1-O-, -(CH2)p1-O-CO-, -(CH2)p1-CO-O-, -(CH2)p1-O-CO-O-, or -CR 0 R 00 -(CH2) p1 -It is.

[0070] In some embodiments of the present invention, the weight percentage of the polymerizable compound of general formula RM in the liquid crystal composition is 0.001% to 5% (including all values ​​therebetween), for example, 0.001%, 0.002%, 0.004%, 0.005%, 0.006%, 0.008%, 0.01%, 0.02%, 0.04%, 0.06%, 0.08%, 0.09%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99%, 100%, 101%, 102%, 103 0.1%, 0.2%, 0.25%, 0.26%, 0.27%, 0.28%, 0.29%, 0.3%, 0.32%, 0.33%, 0.34%, 0.35%, 0.4%, 0.5%, 0.6%, 0.8%, 1%, 1.2%, 1.6%, 1.8%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5% or a range of values ​​between any two of them.

[0071] In some embodiments of the present invention, the liquid crystal composition further comprises at least one additive.

[0072] In addition to the above compounds, the liquid crystal composition of the present invention may contain a general nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, a dopant, an antioxidant, an ultraviolet absorber, an infrared absorber, a polymerizable monomer, or a light stabilizer.

[0073] Dopants that may be preferably added to the liquid crystal composition according to the present invention are as follows: [ka] [ka] is.

[0074] In some embodiments of the present invention, the weight percentage of the dopant in the liquid crystal composition is 0% to 5%, and preferably the weight percentage of the dopant in the liquid crystal composition is 0.01% to 1%.

[0075] The additives used in the liquid crystal composition of the present invention, such as antioxidants, light stabilizers, and ultraviolet absorbers, are preferably the following substances. [ka] [ka] [ka] In the formula, n represents a positive integer of 1 to 12.

[0076] Preferably, the antioxidant is selected from the compounds listed below. [ka] In some embodiments of the present invention, the total weight percentage of the additives in the liquid crystal composition is 0% to 5%, and preferably the total weight percentage of the additives in the liquid crystal composition is 0.01% to 1%.

[0077] The liquid crystal composition containing the polymerizable compound of the present invention can be polymerized even in the absence of a polymerization initiator, but may further contain a polymerization initiator to promote polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, and acylphosphine oxides.

[0078] Regarding the method for polymerizing the polymerizable compound, since rapid polymerization is desirable, a method of polymerization by irradiation with active energy rays such as ultraviolet rays or electron beams is preferred. When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used. Furthermore, when polymerization is performed while the liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation side needs to have appropriate transparency to the active energy rays. Alternatively, a mask may be used during light irradiation to polymerize only specific portions, and then the alignment state of the unpolymerized portions may be changed by changing conditions such as an electric field, a magnetic field, or temperature, and then further irradiated with active energy rays to polymerize. In particular, when ultraviolet exposure is performed, it is preferable to apply a voltage to the liquid crystal composition while performing ultraviolet exposure.

[0079] The temperature at which active energy rays such as ultraviolet rays or electron beams are irradiated is preferably within a temperature range in which the liquid crystal composition of the present invention maintains its liquid crystal state. Polymerization is preferably carried out at a temperature close to room temperature (i.e., 15 to 35°C). Lamps that generate ultraviolet rays include metal halide lamps, high-pressure mercury lamps, and ultra-high-pressure mercury lamps. Regarding the wavelength of the irradiated ultraviolet rays, it is preferable to irradiate ultraviolet rays having a wavelength outside the absorption wavelength range of the liquid crystal composition, and it is preferable to use ultraviolet rays that are blocked as necessary. The intensity of the irradiated ultraviolet rays is preferably 0.1 mW / cm. 2 ~50mW / cm 2 When irradiating ultraviolet rays, the intensity can be changed, and the irradiation time of ultraviolet rays can be appropriately selected depending on the intensity of the ultraviolet rays to be irradiated, and is preferably 10 seconds to 600 seconds.

[0080] In another aspect, the present invention further provides a liquid crystal display device comprising the liquid crystal composition.

[0081] In some embodiments of the present invention, the liquid crystal composition is particularly applicable to a VA, IPS or FFS type display device. [Effects of the Invention]

[0082] Compared with the prior art, the liquid crystal compound of the present invention has a high clearing point, a large optical anisotropy, and an equivalent or higher absolute value of dielectric anisotropy while maintaining an appropriate rotational viscosity. A liquid crystal composition containing the liquid crystal compound of the present invention has a large optical anisotropy, a small rotational viscosity, a high VHR(UV), and a long low-temperature storage time while maintaining an appropriate clearing point, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR(initial), so that a liquid crystal display device containing the liquid crystal composition has high contrast, a fast response speed, high reliability, and high low-temperature storage stability. [Brief explanation of the drawings]

[0083] [Figure 1] 1 is a mass spectrum of compound F-2-4. [Figure 2] 1 is a DSC cooling spectrum of compound F-2-4. [Figure 3] 1 is a DSC temperature-rising spectrum of compound F-2-4. [Figure 4] 1 is a mass spectrum of compound F-1-4. [Figure 5] 1 is a DSC cooling spectrum of compound F-1-4. [Figure 6] 1 is a DSC temperature rise spectrum of compound F-1-4. DETAILED DESCRIPTION OF THE INVENTION

[0084] The present invention will be described below with reference to specific embodiments. Note that the following examples are illustrative of the present invention and are intended to explain the present invention only, not to limit the present invention. Other combinations and various improvements within the concept of the present invention can be made without departing from the spirit or scope of the present invention.

[0085] In the present invention, unless otherwise specified, all contents refer to percentages by weight.

[0086] For ease of explanation, in each of the following examples, the radical structure of each compound is represented by the code shown in Table 2.

[0087] [Table 2]

[0088] Take the following structural formula as an example: [ka] When the structural formula is represented by the code shown in Table 2, it can be represented as nCCGF, where n in the code represents the number of C atoms in the alkyl group at the left end. For example, when n is "3", the alkyl group is -C3H7. C in the code represents a 1,4-cyclohexylene group, G represents a 2-fluoro-1,4-phenylene group, and F represents a fluorine substituent.

[0089] The abbreviations for the test items in the following examples are as follows. Cp Clearing point (nematic-isotropic phase transition temperature, °C) Δn Optical anisotropy (589nm, 20℃) Δε Dielectric constant anisotropy (1KHz, 20℃) VHR (initial) Initial voltage retention rate (%) VHR(UV) Voltage retention rate (%) after ultraviolet light (UV) irradiation t -30℃ Low temperature storage time (days, -30℃) γ1 rotational viscosity (mPa·s, 20℃) Cp is obtained by testing with a melting point apparatus. Δn is obtained by testing at 20° C. using an Abbe refractometer under a sodium lamp (589 nm) light source. For Δε, Δε=ε || -ε ⊥ and ε || is the dielectric constant parallel to the molecular axis, and ε ⊥ is the dielectric constant perpendicular to the molecular axis, and the test conditions are 20°C, 1KHz, and a VA type test box with a thickness of 6 μm. VHR (initial) is the initial voltage holding ratio, which is obtained by testing using a TOY06254 type liquid crystal physical property evaluation system, with a test temperature of 60°C, a test voltage of 5V, a test frequency of 6Hz, and a TN type test box with a thickness of 9μm. VHR (UV) was obtained by testing using a TOY06254 liquid crystal physical property evaluation system, with a wavelength of 365 nm and energy of 6000 mJ / cm 2 The liquid crystal is irradiated with UV light and then tested, the test temperature is 60°C, the test voltage is 5V, the test frequency is 6Hz, and a TN type test box with a thickness of 9μm is used. t -30℃ is the time recorded when a nematic phase liquid crystal medium is placed in a glass bottle and stored at −30° C. and crystal precipitation is observed. γ1 was obtained by a test using an LCM-2 type liquid crystal physical property evaluation system, and the test conditions were 20° C., 160 to 240 V, and a test box with a thickness of 20 μm.

[0090] The liquid crystal compounds of the general formula F of the present invention can be prepared by conventional organic synthesis methods, and methods for introducing target terminal groups, ring structures, and linking groups into starting materials are described in books such as Organic Synthesis (John Wiley & Sons Inc.), Organic Reactions (John Wiley & Sons Inc.), and Comprehensive Organic Synthesis (Pergamon Press).

[0091] Linking group Z in liquid crystal compounds of general formula F F1 ~Z F3 The synthesis method of MSG can be seen in the following scheme. 1 or MSG 2 is a monovalent organic group having at least one ring, and the multiple MSGs used in the following schemes 1 (or MSG 2 ) may be the same or different.

[0092] (1) Synthesis of a single bond [ka] The single-bond compound IA is obtained by reacting arylboronic acid 1 with compound 2, synthesized by a known method, in the presence of a catalyst (e.g., tetrakis(triphenylphosphine)palladium (Pd(PPh3)4)) in aqueous sodium carbonate. Alternatively, compound 3, synthesized by a known method, can be reacted with n-butyllithium (n-BuLi), further with zinc chloride, and then reacted with compound 2 in the presence of a catalyst (dichlorobis(triphenylphosphine)palladium (PdCl2(PPh3)2)).

[0093] (2) Synthesis of -CO-O- and -O-CO- [ka] Compound 3 is reacted with n-butyllithium and then with carbon dioxide to obtain carboxylic acid 4. Compound 4 and compound 5, synthesized by a known method, are dehydrated in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) to synthesize compound IB having a -CO-O- group. Compounds having a -O-CO- group can also be synthesized by this method.

[0094] (3) Synthesis of -CF2O- and -OCF2- [ka] See M. Kuroboshi et al., Chem. Lett., 1992, 827, where compound IB was treated with a sulfurizing agent (e.g., Lawesson's reagent) to obtain compound 6, which was then fluorinated with hydrogen fluoride-pyridine (HF-Py) and N-bromosuccinimide (NBS) to synthesize compound IC having -CF2O-. See W.H. Bunnell et al., J. Org. Chem, 1990, 55, 768, where compound 6 was fluorinated with (diethylamino)sulfur trifluoride (DAST) to prepare compound IC having -CF2O-. These methods can also be used to synthesize compounds having -OCF2-.

[0095] (4) Synthesis of -CH=CH- [ka] Compound 3 is reacted with n-butyllithium, followed by reaction with formamide (e.g., N,N-dimethylformamide (DMF)) to obtain compound 7. The phosphonium salt 8, synthesized by a known method, is reacted with potassium tert-butoxide (t-BuOK) to produce compound ID, which is then reacted with compound 7. Depending on the reaction conditions, the cis isomer is produced by the above method. It should be understood that the cis isomer can be converted to the trans isomer by a known method, if necessary.

[0096] (5) Synthesis of -CH2CH2- [ka] Compound ID can be hydrogenated using a catalyst (eg, palladium on carbon (Pd / C)) to prepare compound IE.

[0097] (6) Synthesis of -CH2O- or -OCH2- [ka] Compound 7 is reduced with sodium borohydride (NaBH4) to obtain compound 9. Compound 9 is then halogenated with hydrobromic acid to obtain compound 10, or the hydroxyl group of compound 9 is protected with p-toluenesulfonic acid (TsOH) to obtain compound 11. Compound 10 or compound 11 is then reacted with compound 5 in the presence of potassium carbonate to obtain compound IF. Compounds having -OCH2- can also be synthesized by these methods.

[0098] (7) Synthesis of -CH=CF2 [ka] Compound IG can be prepared by removing the hydrofluoric acid at the end chain of compound 11 with a solution of lithium diisopropylamide (LDA) in tetrahydrofuran.

[0099] For ring structures such as a 1,4-cyclohexylene group, a 1,3-dioxane-2,5-diyl group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 2,3-difluoro-1,4-phenylene group, a 2,5-difluoro-1,4-phenylene group, a 2,6-difluoro-1,4-phenylene group, and a 2,3,5,6-tetrafluoro-1,4-phenylene group, starting materials are already commercially available, or their synthesis methods are known in the art.

[0100] A preferred method for synthesizing representative compounds is shown below. [Synthesis Example 1]

[0101] The synthetic route of compound F-2-4 is shown below. [ka]

[0102] Step 1: Preparation of Compounds of Formula B-3 In a 2 L reaction flask, 99 g of the compound of general formula B-1 ((4-butoxy-2,3-difluorophenyl)boronic acid), 100 g of the compound of general formula B-2 (2-bromo-6-fluorophenol), and 110 g of sodium carbonate were added and thoroughly dissolved in 1.2 L of a mixed solvent consisting of toluene, ethanol, and water (the volume ratio of toluene, ethanol, and water was 2:1:1). Under the protection of a nitrogen atmosphere, 1.8 g of Pd(PPh3)4 was added and the mixture was refluxed at 100 °C for 6 hours. The reaction solution is cooled to room temperature, 300 mL of water is added to separate the layers, the aqueous phase is extracted with 20 mL of toluene, the organic phases are combined, the organic phase is washed with saturated aqueous NaCl until the pH becomes 7, dried over anhydrous Na2SO4, concentrated, and recrystallized from a mixed solvent of petroleum ether and toluene (the volume ratio of petroleum ether to toluene is 24:1) to obtain 109.5 g of a white solid compound of general formula B-3 (4'-butoxy-2',3',3-trifluoro-[1,1'-biphenyl]-2-ol) (yield: 85%).

[0103] Step 2: Preparation of Compounds of Formula B-4 In a 2 L reaction flask, 110 g of the compound of general formula B-3 and 72 g of potassium carbonate are added, thoroughly dissolved in 700 mL of N,N-dimethylformamide, and reacted for 9 hours at 120° C. The reaction mixture is cooled to room temperature, 3.5 L of water is added, stirred, and suction filtered to obtain a crude product, which is slurried in ethanol, suction filtered, and dried over anhydrous NaSO to obtain 88.5 g of the compound of general formula B-4 (3-butoxy-4,6-difluorodibenzo[b,d]furan) as a gray solid (yield: 86.3%).

[0104] Step 3: Preparation of Compounds of Formula B-5 Add 38g of diisopropylamine to a 2L reaction flask and dissolve it thoroughly in 500mL of tetrahydrofuran. Under nitrogen atmosphere protection, add 150mL of n-butyllithium at a temperature controlled at -20°C and react for 3 hours at a temperature controlled at -20°C. Add 90g of the compound of general formula B-4 and react for 3 hours at a temperature controlled at -78°C. Add 70g of triisopropyl borate and react for 3 hours at a temperature controlled at 78°C. The pH is adjusted to 2-3 with dilute hydrochloric acid, the layers are separated, the aqueous phase is extracted with ethyl acetate, the organic phases are combined, the organic phase is washed with saturated aqueous NaCl until the pH is 7, dried over anhydrous Na2SO4, concentrated, slurried in dichloromethane, suction filtered, and the filter cake is dried to obtain 73 g of a white solid, the compound of general formula B-5 ((4,6-difluoro-7-butoxydibenzo[b,d]furan-3-yl)boronic acid) (yield: 70%).

[0105] Step 4: Preparation of Compounds of Formula B-6 In a 2L reaction flask, 70g of the compound of general formula B-5 was added, and the solution was thoroughly dissolved in 700mL of tetrahydrofuran. The temperature was controlled at 10°C, and 68g of 30% aqueous hydrogen peroxide was added. The temperature was controlled at 10°C, and the reaction was continued for 9 hours. The mixture was quenched with 500mL of 5% sodium thiosulfate solution, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated aqueous NaCl solution until the pH was 7. The mixture was dried over anhydrous Na2SO4, concentrated, slurried in 25mL of dichloromethane, and suction filtered. The filter cake was dried to obtain 55.6g of the compound of general formula B-6 (4,6-difluoro-7-butoxydibenzo[b,d]furan-3-ol), which is a white solid (yield: 90%).

[0106] Step 5: Preparation of Compounds of Formula B-7 In a 2L reaction flask, 70g of the compound of general formula B-6 was added, and the solution was thoroughly dissolved in 700mL of tetrahydrofuran. The temperature was controlled at 10°C, and 68g of trifluoroethanol was added. The temperature was controlled at 10°C, and the reaction was continued for 9 hours. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated aqueous NaCl solution until pH=7, dried over anhydrous Na2SO4, concentrated, slurried in 25mL of dichloromethane, and suction filtered. The filter cake was dried to obtain 53.8g of the compound of general formula B-7 (4,6-difluoro-3-butoxy-7-(2,2,2-trifluoroethoxy)dibenzo[b,d]furan) as a white solid (yield: 60%).

[0107] Step 6: Preparation of compounds of formula F-2-4 In a 2L reaction flask, 40g of the compound of general formula B-7 was added, and it was thoroughly dissolved in 700mL of tetrahydrofuran. The temperature was controlled at 10°C, and 40g of 30% sodium hydroxide solution was added, and the reaction was continued for 8 hours. The reaction was quenched with 500mL of 5% sodium thiosulfate, and the layers were separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated aqueous NaCl solution until pH=7, dried over anhydrous Na2SO4, concentrated, slurried in 25mL of dichloromethane, suction filtered, and dried on the filter cake to obtain 28.4g of a white solid compound of general formula F-2-4 (3-((2,2-difluorovinyl)oxy)-4,6-difluoro-7-butoxydibenzo[b,d]furan) (yield: 75%).

[0108] The mass spectrum of the compound of general formula F-2-4 is shown in FIG.

[0109] The DSC cooling spectrum of the compound of general formula F-2-4 is shown in FIG.

[0110] The DSC temperature rise spectrum of the compound of general formula F-2-4 is shown in FIG. [Synthesis Example 2]

[0111] The synthetic route of compound F-1-4 is shown below. [ka]

[0112] The compound of the general formula B-3 was synthesized in the same manner as in Synthesis Example 1.

[0113] Step 1, Preparation of Compounds of Formula B-8 In a 1 L reaction flask, 120 g of the compound of general formula B-3, 120 g of dimethylthiocarbamoyl chloride and 90 g of triethylamine are added, and the mixture is thoroughly dissolved in 440 mL of isododecane. Under the protective condition of a nitrogen atmosphere, the temperature is controlled at 165 ° C. to reflux the mixture for 18 hours, and the mixture is cooled to 25 ° C., filtered with suction, recrystallized with ethanol, filtered with suction, and the filter cake is dried to obtain 78.9 g of a brown solid compound of general formula B-8 (3-butoxy-4,6-difluorodibenzo[b,d]thiophene) (yield: 66.667%).

[0114] Step 2: Preparation of Compounds of Formula B-9 Add 38g of diisopropylamine to a 2L reaction flask and dissolve it thoroughly in 500mL of tetrahydrofuran. Under nitrogen atmosphere protection, add 150mL of n-butyllithium at a temperature controlled at -20°C and react for 3 hours at a temperature controlled at -20°C. Add 80g of the compound of general formula B-8 and react for 3 hours at a temperature controlled at -78°C. Add 70g of triisopropyl borate and react for 3 hours at a temperature controlled at 78°C. The pH is adjusted to 2-3 with dilute hydrochloric acid, the layers are separated, the aqueous phase is extracted with ethyl acetate, the organic phases are combined, the organic phase is washed with saturated aqueous NaCl until the pH is 7, dried over anhydrous Na2SO4, concentrated, slurried in dichloromethane, suction filtered, and the filter cake is dried to obtain 69 g of a white solid, the compound of general formula B-9 ((4,6-difluoro-7-butoxydibenzo[b,d]thiophen-3-yl)boronic acid) (yield: 75%).

[0115] Step 3: Preparation of Compounds of Formula B-10 In a 2L reaction flask, 70g of the compound of general formula B-9 was added, and the solution was thoroughly dissolved in 700mL of tetrahydrofuran. The temperature was controlled at 10°C, and 80g of 30% hydrogen peroxide solution was added. The temperature was controlled at 10°C, and the reaction was continued for 9 hours. The mixture was quenched with 500mL of 5% sodium thiosulfate solution, and the mixture was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated aqueous NaCl solution until pH = 7, and then dried over anhydrous Na2SO4. The mixture was concentrated, slurried in 25mL of dichloromethane, and suction filtered. The filter cake was dried to obtain 41.3g of the compound of general formula B-10 (4,6-difluoro-7-butoxydibenzo[b,d]thiophen-3-ol), which is a white solid (yield: 64.3%).

[0116] Step 4: Preparation of Compounds of Formula B-11 In a 2L reaction flask, 70g of the compound of general formula B-10 was added, and the solution was thoroughly dissolved in 700mL of tetrahydrofuran. The temperature was controlled at 10°C, and 68g of trifluoroethanol was added. The temperature was controlled at 10°C, and the reaction was continued for 9 hours. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated aqueous NaCl solution until pH=7, dried over anhydrous Na2SO4, concentrated, slurried in 25mL of dichloromethane, and suction filtered. The filter cake was dried to obtain 56.7g of a white solid compound of general formula B-11 (4,6-difluoro-3-butoxy-7-(2,2,2-trifluoroethoxy)dibenzo[b,d]furan) (yield: 64%).

[0117] Step 5: Preparation of compounds of general formula F-1-4 In a 2L reaction flask, add 40g of the compound of general formula B-11, dissolve it thoroughly in 700mL of tetrahydrofuran, control the temperature at 10°C, add 40g of 30% sodium hydroxide solution, control the temperature at 10°C and react for 8 hours, quench the reaction with 500mL of 5% sodium thiosulfate, separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, wash the organic phase with saturated aqueous NaCl solution until pH = 7, dry with anhydrous Na2SO4, concentrate, slurry with 25mL of dichloromethane, suction filter, and dry the filter cake to obtain 30.4g of a white solid compound of general formula F-1-4 (3-((2,2-difluorovinyl)oxy)-4,6-difluoro-7-butoxydibenzo[b,d]furan) (yield: 80%).

[0118] The mass spectrum of the compound of general formula F-1-4 is shown in FIG.

[0119] The DSC cooling spectrum of the compound of general formula F-1-4 is shown in FIG.

[0120] The DSC temperature rise spectrum of the compound of general formula F-1-4 is shown in FIG.

[0121] The compound of formula F prepared in the above examples and the compound DB-1 ( [ka] ) and DB-2( [ka] ) and the base liquid crystal were mixed at a ratio of 10% by weight:90% by weight to obtain a mixture. The performance parameter values ​​of the test compound were calculated using the extrapolation method, and the extrapolated values ​​of Cp, Δn, and Δε were calculated as follows: ((measured value of the mixture) - 0.9 × (measured value of the base liquid crystal)) / 0.1, and the extrapolated value of γ1 = 10 10(lgA-0.9lgB) where A is the γ1 of the mixture and B is the γ1 of the parent liquid crystal. Following this method, performance parameters such as the clearing point Cp, optical anisotropy Δn, dielectric anisotropy Δε, and rotational viscosity γ1 are derived.

[0122] [Table 3]

[0123] The extrapolated liquid crystal performance parameters of the above compounds are shown in Table 4 below.

[0124] [Table 4]

[0125] A comparison of the test results for the performance parameters of compounds DB-1, DB-2 and the compound of general formula F of the present invention in Table 4 shows that the compound of general formula F of the present invention has a higher clearing point, a larger optical anisotropy and the same or higher absolute value of dielectric anisotropy while maintaining an appropriate rotational viscosity.

[0126] The components used in the following examples can be synthesized by known methods or obtained commercially. These synthesis techniques are common, and the resulting liquid crystal compounds meet the standards for electronic compounds.

[0127] In the present invention, unless otherwise specified, all contents refer to percentages by weight.

[0128] Liquid crystal compositions are prepared according to the blending ratios of the liquid crystal compositions specified in the following examples. The liquid crystal compositions are prepared by a method commonly used in the art, for example, by mixing the liquid crystal compositions according to the blending ratios using methods such as heating, ultrasonic waves, and suspension. [Application comparison example 1]

[0129] According to the compounds and their weight percentages shown in Table 5, a liquid crystal composition of Comparative Application Example 1 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0130] [Table 5] [Application Example 1]

[0131] According to each compound and its weight percentage shown in Table 6, a liquid crystal composition of Application Example 1 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0132] [Table 6]

[0133] A comparison between Application Example 1 and Application Example 1 shows that the liquid crystal composition of the present invention has a small rotational viscosity, a high VHR(UV) and a long low-temperature storage time while maintaining a suitable clearing point, suitable optical anisotropy, suitable dielectric anisotropy and suitable VHR(initial). [Application Comparison Example 2]

[0134] According to the compounds and their weight percentages shown in Table 7, a liquid crystal composition of Comparative Application Example 2 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0135] [Table 7] [Application Example 2]

[0136] According to the compounds and their weight percentages shown in Table 8, the liquid crystal composition of Application Example 2 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0137] [Table 8]

[0138] A comparison between Application Example 2 and Application Example 2 reveals that the liquid crystal composition of the present invention has a large optical anisotropy, a small rotational viscosity, a high VHR(UV), and a long low-temperature storage time while maintaining an appropriate clearing point, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR(initial). [Application Comparison Example 3]

[0139] According to the compounds and their weight percentages shown in Table 9, a liquid crystal composition of Comparative Application Example 3 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0140] [Table 9] [Application Example 3]

[0141] According to the compounds and their weight percentages shown in Table 10, the liquid crystal composition of Application Example 3 is prepared, and the liquid crystal composition is filled between the two substrates of a liquid crystal display to carry out a performance test.

[0142] [Table 10]

[0143] A comparison between Application Example 3 and Application Example 3 shows that the liquid crystal composition of the present invention has a small rotational viscosity, a high VHR(UV) and a long low-temperature storage time while maintaining an appropriate clearing point, appropriate optical anisotropy, appropriate absolute value of dielectric anisotropy and appropriate VHR(initial). [Application Example 4]

[0144] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 11, and 0.3% by weight of [ka] The above was added to the liquid crystal composition shown in Table 11 to prepare Application Example 4, and the liquid crystal composition was filled between both substrates of a liquid crystal display to carry out a performance test.

[0145] [Table 11] [Application Example 5]

[0146] When 0.3% of the polymerizable compound RM-1-1 is added to the liquid crystal composition in Example 1, polymerization can be realized, and a fast angle formation speed and a small pretilt angle are formed. [ka] [Application Example 6]

[0147] When 0.3% of the polymerizable compound RM-2-1 is added to the liquid crystal composition in Example 2, polymerization can be realized, and a fast angle formation speed and a small pretilt angle are formed. [ka] [Application Example 7]

[0148] According to the compounds and their weight percentages shown in Table 12, the liquid crystal composition of Application Example 7 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0149] [Table 12] [Application Example 8]

[0150] According to the compounds and their weight percentages shown in Table 13, the liquid crystal composition of Application Example 8 is prepared, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0151] [Table 13] [Application Example 9]

[0152] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 14, and 0.3% by weight of [ka] The above is added to the liquid crystal composition shown in Table 14 to prepare Application Example 9, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0153] [Table 14] [Application Example 10]

[0154] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 15, and 0.3% by weight of [ka] The above was added to the liquid crystal composition shown in Table 15 to prepare Application Example 10, and the liquid crystal composition was filled between both substrates of a liquid crystal display to carry out a performance test.

[0155] [Table 15] [Application Example 11]

[0156] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 16, and 0.3% by weight of [ka] The above was added to the liquid crystal composition shown in Table 16 to prepare Application Example 11, and the liquid crystal composition was filled between both substrates of a liquid crystal display to carry out a performance test.

[0157] [Table 16] [Application Example 12]

[0158] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 17, and 0.3% by weight of [ka] The above is added to the liquid crystal composition shown in Table 17 to prepare Application Example 12, and the liquid crystal composition is filled between both substrates of a liquid crystal display to carry out a performance test.

[0159] [Table 17] [Application Example 13]

[0160] A liquid crystal composition was prepared according to the compounds and their weight percentages shown in Table 18, and 0.3% by weight of [ka] The above was added to the liquid crystal composition shown in Table 18 to prepare Application Example 13, and the liquid crystal composition was filled between both substrates of a liquid crystal display to carry out a performance test.

[0161] [Table 18]

[0162] From the above, the liquid crystal compound of general formula F according to the present invention has a high clearing point, a large optical anisotropy, and an equivalent or higher absolute value of dielectric anisotropy while maintaining an appropriate rotational viscosity, and the liquid crystal composition of the present invention has a large optical anisotropy, a small rotational viscosity, a high VHR(UV), and a long low-temperature storage time while maintaining an appropriate clearing point, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR(initial), so that a liquid crystal display device including the liquid crystal composition has high contrast, a fast response speed, high reliability, and high low-temperature storage stability.

[0163] The above embodiments are merely intended to explain the technical ideas and features of the present invention so that those skilled in the art can understand and practice the contents of the present invention, and are not intended to limit the protection scope of the present invention. Any equivalent modifications or alterations made based on the gist of the present invention should be included within the protection scope of the present invention. [Industrial Applicability]

[0164] The liquid crystal compound, the liquid crystal composition thereof, and the liquid crystal display device according to the present invention can be applied to the field of liquid crystals.

Claims

1. A liquid crystal compound of the general formula F. 【Chemistry 1】 (In the formula, R Ｆ１ is —H, a halogen, a linear or branched alkyl group containing 1 to 12 carbon atoms, 【Chemistry 2】 or 【Transformation 3】 wherein the linear or branched alkyl group having 1 to 12 carbon atoms has one or more non-adjacent —CH ２ - may be independently replaced by -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H in the linear or branched alkyl group having 1 to 12 carbon atoms may be independently replaced by -F or -Cl; ring 【Chemistry 4】 and ring 【Transformation 5】 are each independently 【Transformation 6】 or 【Transformation 7】 represents 【Transformation 8】 and 【Chemistry 9】 One or more —CH ２ - may be replaced by -O-, and one or more single bonds in the ring may be replaced by a double bond; 【Chemistry 10】 and 【Chemistry 11】 one or more —H in the ring may each independently be replaced by —CN, —F, or —Cl, and one or more —CH═ in the ring may each independently be replaced by —N═; X Ｆ represents —O—, —S—, or —CO—; L Ｆ１ and L Ｆ２ are each independently —H, —F, —Cl, or —CF ３ or -OCF ３ represents Z Ｆ１ and Z Ｆ２ are each independently a single bond, —CO—O—, —O—CO—, or —CH ２ O-, -OCH ２ -, -CH=CH-, -C≡C-, -CH ２ CH ２ -, -CF ２ CF ２ -, -(CH ２ ) ４ -, -CF ２ O- or -OCF ２ represents -, n Ｆ１ represents 0, 1 or 2, n Ｆ２ represents 0, and n Ｆ１ If represents 2, the ring 【Chemistry 12】 may be the same or different, and n Ｆ３ represents 0.)

2. The compound of general formula F is 【Chemistry 13】 is selected from the group consisting of compounds During the ceremony, X Ｆ１ and X Ｆ２ are each independently —CH ２ 2. The liquid crystal compound according to claim 1, wherein the compound represents - or -O-.

3. A liquid crystal composition comprising at least one liquid crystal compound of general formula F according to claim 1.

4. 4. The liquid crystal composition according to claim 3, further comprising at least one compound of general formula N. 【Chemistry 14】 (In the formula, R Ｎ１ and R Ｎ２ are each independently a straight or branched chain alkyl group containing 1 to 12 carbon atoms; 【Chemistry 15】 or 【Chemistry 16】 wherein the linear or branched alkyl group having 1 to 12 carbon atoms has one or more non-adjacent —CH ２ - may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; ring 【Chemistry 17】 and ring [Chemistry 18] are each independently 【Chemistry 19】 or 【Chemistry 20】 represents 【Chemistry 21】 One or more —CH ２ - may be replaced by -O-, and one or more single bonds in the ring may be replaced by a double bond; 【Chemistry 22】 one or more —H in the ring may each independently be replaced by —F, —Cl, or —CN, and one or more —CH═ in the ring may each independently be replaced by —N═; Z Ｎ１ and Z Ｎ２ are each independently a single bond, —CO—O—, —O—CO—, or —CH ２ O-, -OCH ２ -, -CH=CH-, -C≡C-, -CH ２ CH ２ -, -CF ２ CF ２ -, -(CH ２ ) ４ -, -CF ２ O- or -OCF ２ represents -, L Ｎ１ and L Ｎ２ each independently represents —H, an alkyl group containing 1 to 3 carbon atoms, or a halogen; and n Ｎ１ represents 0, 1, 2 or 3; n Ｎ２ represents 0 or 1, and 0≦n Ｎ１ +n Ｎ２ ≦3, and n Ｎ１ = 2 or 3, the ring 【Chemistry 23】 may be the same or different, Z Ｎ１ may be the same or different.)

5. The compound of general formula N is 【Chemistry 24(1)】 【Chemistry 24(2)】 【Chemistry 24(3)】 5. The liquid crystal composition according to claim 4, wherein the compound is selected from the group consisting of the compounds:

6. 5. The liquid crystal composition according to claim 4, further comprising at least one compound of general formula M: 【Chemistry 25】 (In the formula, R Ｍ１ and R Ｍ２ are each independently a straight or branched chain alkyl group containing 1 to 12 carbon atoms; 【Chemistry 26】 or 【Chemistry 27】 wherein the linear or branched alkyl group having 1 to 12 carbon atoms has one or more non-adjacent —CH ２ - may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; ring 【Chemistry 28】 ,ring 【Chemistry 29】 and ring 【Transformation 30】 are each independently 【Chemistry 31】 or 【Chemistry 32】 represents 【Transformation 33】 One or more —CH ２ - may be replaced by -O-, and one or more single bonds in the ring may be replaced by a double bond; 【Transformation 34】 wherein at most one —H may be replaced by halogen; Z Ｍ１ and Z Ｍ２ are each independently a single bond, —CO—O—, —O—CO—, or —CH ２ O-, -OCH ２ -, -C≡C-, -CH=CH-, -CH ２ CH ２ - or - (CH ２ ) ４ represents - and n Ｍ represents 0, 1 or 2, n Ｍ If =2, the ring 【Chemistry 35】 may be the same or different, Z Ｍ２ may be the same or different.)

7. The compound of general formula M is 【Chemistry 36(1)】 【Chemistry 36(2)】 【Chemistry 36(3)】 7. The liquid crystal composition according to claim 6, wherein the compound is selected from the group consisting of the compounds:

8. 7. The liquid crystal composition of claim 6, further comprising at least one polymerizable compound of general formula RM. 【Chemistry 37】 (In the formula, R １ -H, halogen, -CN, -Sp ２ -P ２ or a linear or branched alkyl group containing 1 to 12 carbon atoms; 【Transformation 38】 or 【Chemistry 39】 wherein the linear or branched alkyl group having 1 to 12 carbon atoms represents 【Chemistry 40】 or 【Chemistry 41】 or two or more non-adjacent —CH ２ each - may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; one or more -H may be independently replaced by -F or -Cl; ring 【Chemistry 42】 and ring 【Chemistry 43】 are each independently 【Chemistry 44】 or 【Chemistry 45】 represents 【Chemistry 46】 and 【Chemistry 47】 One or more —CH ２ - may be replaced by -O-, and one or more single bonds in the ring may be replaced by a double bond; 【Chemistry 48】 and 【Chemistry 49】 In the formula (I), one or more —H are each independently —F, —Cl, —CN, or —Sp. ３ -P ３ , a halogenated or non-halogenated straight-chain alkyl group containing 1 to 12 carbon atoms, a halogenated or non-halogenated straight-chain alkoxy group containing 1 to 11 carbon atoms, [Transformation 50] or 【Chemistry 51】 and one or more -CH= in the ring may be replaced by -N=; ring 【Chemistry 52】 teeth, 【Chemistry 53】 or 【Chemistry 54】 represents 【Transformation 55】 or 【Transformation 56】 In the formula (I), one or more —H are each independently —F, —Cl, —CN, or —Sp. ３ -P ３ , a halogenated or non-halogenated straight-chain alkyl group containing 1 to 12 carbon atoms, a halogenated or non-halogenated straight-chain alkoxy group containing 1 to 11 carbon atoms, 【Chemistry 57】 or 【Chemistry 58】 and one or more -CH= in the ring may be replaced by -N=; P １ , P ２ and P ３ each independently represents a polymerizable group, The polymerizable group is 【Chemistry 59】 or represents -SH, Sp １ , Sp ２ and Sp ３ each independently represents a spacer group or a single bond, The spacer group is —(CH ２ ) p １ -, -(CH ２ CH ２ O) q １ -CH ２ CH ２ -, -(CH ２ CH ２ S)q １ -CH ２ CH ２ -, -(CH ２ CH ２ N.H.)q １ -CH ２ CH ２ -, -CR ０ R ００ - (CH ２ ) ｐ１ -or-(SiR ０ R ００ -O)p １ - and p １ represents an integer from 1 to 12, and q １ represents an integer of 1 to 3, R ０ and R ００ each independently represents —H, a linear or branched alkyl group containing 1 to 12 carbon atoms, or a cyclic alkyl group containing 3 to 12 carbon atoms; Z １ and Z ２ are each independently —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CH ２ O-, -OCH ２ -, -CH ２ S-, -SCH ２ -, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -(CH ２ ) ｄ -, -CF ２ CH ２ -, -CH ２ CF ２ -, - (CF ２ ) ｄ -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH ２ CH ２ -CO-O-, -O-CO-CH ２ CH ２ --, --CHR １ -, -CR １ R ２ represents - or a single bond, R １ and R ２ each independently represents a linear or branched alkyl group containing 1 to 12 carbon atoms, and d represents an integer of 1 to 4; X ０ is -O-, -S-, -CO-, -CF ２ represents -, -NH- or -NF-; a represents 0, 1 or 2, b represents 0 or 1, and when a represents 2, the ring 【Transformation 60】 may be the same or different, Z １ may be the same or different.)

9. 9. The liquid crystal composition according to claim 8, wherein the weight percentage of the compound of general formula F in the liquid crystal composition is 0.1% to 30%, the weight percentage of the compound of general formula N in the liquid crystal composition is 0.1% to 70%, the weight percentage of the compound of general formula M in the liquid crystal composition is 0.1% to 70%, and the weight percentage of the polymerizable compound of general formula RM in the liquid crystal composition is 0.001% to 5%.

10. Further comprising at least one additive, the structural formula of which is: 【Chemistry 61】 4. The liquid crystal composition according to claim 3, wherein n is a positive integer of 1 to 12.

11. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 3 to 10.

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