Liquid crystal composition and liquid crystal display device containing the same

By using specific compound formulations in liquid crystal compositions, the rotation viscosity and voltage retention of liquid crystals are solved, and the problem of insufficient performance of existing negative liquid crystal compositions in high-resolution displays is achieved, faster Response speed and higher reliability.

CN116064045BActive Publication Date: 2025-02-07JIANGSU HECHENG DISPLAY TECH CO LTD
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Patent Information

Application Number
CN202111284829.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2021-11-01
Publication Date
2025-02-07
Estimated Expiration
2041-11-01

AI Technical Summary

Technical Problem

The existing negative liquid crystal compositions have large rotational viscosity, low voltage retention rate and ultraviolet stability, which are difficult to meet the needs of high-resolution liquid crystal displays.

Method used

The liquid crystal composition formulations comprising at least one compound of general formula F, compound of general formula I and compound of general formula II are used to adjust the rotational viscosity and voltage retention rate of the liquid crystal by optimizing the content and structure of the compound.

Benefits of technology

While maintaining the absolute values ​​of appropriate bright spots, optical anisotropy and dielectric anisotropy, the rotational viscosity of the liquid crystal is significantly reduced, and the voltage retention rate under ultraviolet light is improved, which improves the response speed and reliability of the liquid crystal display. .

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Abstract

The present invention provides a liquid crystal composition and a liquid crystal display device comprising the same, wherein the liquid crystal composition comprises at least one compound of general formula F, at least one compound of general formula I and at least one compound of general formula II. The liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy and an appropriate VHR (initial), so that the liquid crystal display device comprising the same has a faster response speed, better low temperature stability and higher reliability.
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Description

Technical Field

[0001] The present invention relates to the field of liquid crystals, and in particular to a liquid crystal composition and a liquid crystal display device comprising the liquid crystal composition. Background Art

[0002] Liquid crystal display elements can be used in various household appliances represented by clocks and electronic calculators, measuring machines, automotive panels, word processors, computers, printers, televisions, etc. According to the type of display mode, liquid crystal display elements can be divided into PC (phase change), TN (twist nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), etc. According to the driving method of the element, liquid crystal display elements can be divided into PM (passive matrix) type and AM (active matrix) type. PM is divided into static and multiplex types. AM is divided into TFT (thin film transistor), MIM (metal insulator metal) and other types. TFT types include amorphous silicon and polycrystalline silicon. The latter is divided into high temperature type and low temperature type according to the manufacturing process. According to the type of light source, liquid crystal display elements can be divided into reflective type using natural light, transmissive type using background light, and semi-transmissive type using both natural light and backlight.

[0003] The 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 the following Table 1.

[0004] Table 1. Characteristics of liquid crystal composition and AM element

[0005] serial number Characteristics of Liquid Crystal Compositions Characteristics of AM components 1 Nematic phase has a wide temperature range Wide temperature range 2 Low viscosity Short response time 3 Optical anisotropy is appropriate High contrast 4 The absolute value of positive or negative dielectric anisotropy is large Low threshold voltage, low power consumption, high contrast 5 Larger specific resistance High voltage holding rate and contrast ratio 6 UV and heat stable Long life 7 Large elastic constant High contrast and short response time

[0006] In order to improve the response speed of liquid crystal display devices, the rotational viscosity of liquid crystal materials needs to be reduced as much as possible. However, generally, low-viscosity liquid crystal materials have lower clearing points, optical anisotropy, and absolute values ​​of dielectric anisotropy. Therefore, when modulating the formula of mixed liquid crystals, when reducing the viscosity, other performance requirements need to be considered.

[0007] The threshold voltage of the mixed liquid crystal mainly depends on the Δε of the liquid crystal. A large Δε is conducive to reducing the threshold voltage of the liquid crystal. By mixing monomer liquid crystals of different polarities, the Δε of the mixed liquid crystal is modulated to a suitable value to meet the requirements of the operating voltage of the display device. However, increasing the Δε of the liquid crystal may increase the viscosity of the liquid crystal and reduce the stability of the liquid crystal.

[0008] With the improvement of the resolution of liquid crystal displays, 4K and 8K resolution liquid crystal displays are gradually emerging, which in turn requires liquid crystal panels to have a smaller aperture ratio and higher transmittance. Negative liquid crystal compositions have higher transmittance, especially in PSA mode and NFFS mode, where the advantage of high transmittance is more obvious. However, the structure of negative liquid crystals determines that they have a larger rotational viscosity, high ion concentration, and low voltage holding rate, resulting in the negative liquid crystal afterimage effect being significantly inferior to that of positive liquid crystals. Therefore, it is urgent to develop a negative liquid crystal composition with a smaller rotational viscosity and a higher voltage holding rate to improve the shortcomings of existing negative liquid crystals and provide a liquid crystal composition that meets market demand.

[0009] Chinese patent application CN1942461A and German patent application DE10101022A1 disclose a liquid crystal compound that can solve the above problems to a certain extent. Chinese patent application CN107973766A performs ring substitution on the terminal structure of such compounds on the basis of the prior art. However, the compounds disclosed so far have the problems of small absolute value of dielectric anisotropy, large rotational viscosity, low voltage holding rate and poor low-temperature miscibility. Chinese patent applications CN105820824A and CN110577838A disclose a dibenzothiophene / furan liquid crystal composition, which solves the above problems to a certain extent, but still has high rotational viscosity, low VHR, especially low VHR(UV). It is well known that the LCD panel manufacturing process needs to be exposed to a certain degree of UV light. The general wavelength of ultraviolet light is 365nm, and the light dosage is about 6000-1000MJ. After the traditional dibenzofuran and dibenzothiophene compounds are exposed to UV light, their VHR (UV) is low, which reduces the reliability of the display and produces afterimages.

[0010] The modulation of the mixed liquid crystal formula should adjust many physical properties of the liquid crystal at the same time. It is impossible to adjust one performance parameter without affecting the value of another parameter. Sometimes, adding a certain monomer liquid crystal to adjust a certain performance parameter of the mixed liquid crystal may be beneficial to one or several other performance parameters, but may be detrimental to the improvement of other performance parameters. Therefore, how to obtain a liquid crystal composition that can solve or partially solve the above problems is still a problem that needs to be solved urgently in this field. Summary of the invention

[0011] Purpose of the invention: In view of the defects existing in the prior art, the purpose of the present invention is to provide a liquid crystal composition, which has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0012] Another object of the present invention is to provide a liquid crystal display device comprising the liquid crystal composition.

[0013] Technical solution: In order to achieve the above invention objectives, the present invention provides a liquid crystal composition, which comprises at least one compound of general formula F, at least one compound of general formula I and at least one compound of general formula II:

[0014]

[0015] as well as

[0016]

[0017] in,

[0018] R F1 represents -H, halogen, a straight 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, wherein one or more non-adjacent -CH2- in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms may be independently replaced by -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms may be independently replaced by -F or -Cl;

[0019] R1, R2, R3 and R4 each independently represent 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, One or more non-adjacent -CH2- in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-;

[0020] ring and ring Each independently expresses in One or more -CH2- in the ring may be independently replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds, wherein and One or more -H in the ring may be independently replaced by -CN, -F or -Cl, and one or more -CH= in the ring may be replaced by -N=;

[0021] ring express

[0022] X F represents -O-, -S-, or -CO-;

[0023] L F1 , L F2 , L1 and L2 each independently represent -H, -F, -Cl, -CF3 or -OCF3;

[0024] L3, L4, L5 and L6 each independently represent -F, -Cl, -CF3 or -OCF3;

[0025] Z F1 and Z F2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-;

[0026] n F1 and n F2 Each independently represents 0, 1 or 2, where n F1 When it indicates 2, the ring can be the same or different, where n F2 When it indicates 2, the ring Can be the same or different, Z F2 Can be the same or different;

[0027] n F3 represents an integer from 0 to 4; and

[0028] n1 and n2 each independently represent 0 or 1.

[0029] In some embodiments of the present invention, preferably, L F1 and L F2 Each independently represents -F or -Cl.

[0030] In some embodiments of the present invention, the compound of formula F is selected from the group consisting of:

[0031]

[0032]

[0033] as well as

[0034]

[0035] in,

[0036] X F1 and X F2 Each independently represents -CH2- or -O-.

[0037] In some embodiments of the present invention, preferably, n F3 represents 0 or 1; preferably, n F3 Indicates 0.

[0038] In some embodiments of the present invention, preferably, Z F1 and Z F2 Each independently represents a single bond, -CH2O- or -OCH2-, and further preferably, Z F1 and Z F2 Both represent single bonds.

[0039] In some embodiments of the present invention, n F1 and n F2 At least one of them represents 0; preferably, n F1 and n F2 All represent 0.

[0040] In some embodiments of the present invention, preferably, R F1 represents a straight-chain or branched alkyl group containing 1 to 10 carbon atoms, a straight-chain or branched alkoxy group containing 1 to 9 carbon atoms, or a straight-chain or branched alkenyl group containing 2 to 10 carbon atoms; further preferably, R F1 It represents a straight chain or branched chain alkyl group containing 1 to 8 carbon atoms, a straight chain or branched chain alkoxy group containing 1 to 7 carbon atoms, or a straight chain or branched chain alkenyl group containing 2 to 8 carbon atoms.

[0041] In some embodiments of the present invention, in the compounds of formula F-1, the compounds of formula F-2, the compounds of formula F-3, the compounds of formula F-4, the compounds of formula F-18 and the compounds of formula F-19, R F1 represents a straight-chain or branched alkoxy group containing 1 to 7 (e.g., 1, 2, 3, 4, 5, 6 or 7) carbon atoms.

[0042] In some embodiments of the present invention, in order to enable the liquid crystal composition of the present invention to obtain an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, an appropriate VHR (initial), a smaller rotational viscosity and a higher VHR (UV), the compound of general formula F is selected from the group consisting of a compound of general formula F-1, a compound of general formula F-2, a compound of general formula F-5 and a compound of general formula F-6.

[0043] In some embodiments of the present invention, in order to obtain an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, an appropriate VHR (initial), a smaller rotational viscosity and a higher VHR (UV), the liquid crystal composition of the present invention contains at least two compounds of the general formula F, preferably, the liquid crystal composition contains at least two compounds of the general formula F-1.

[0044] In some embodiments of the present invention, it is preferred to adjust the content of the compound of general formula F so that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0045] In some embodiments of the present invention, the weight percentage of the compound of formula F in the liquid crystal composition is 0.1%-30% (including all values ​​therebetween), for example, 0.1%, 0.5%, 1%, 2%, 4%, 5%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30% or any range between two of them.

[0046] In some embodiments of the present invention, preferably, R1 and R2 each independently represent a straight chain or branched alkyl group containing 1-10 carbon atoms, a straight chain or branched alkoxy group containing 1-9 carbon atoms, or a straight chain or branched alkenyl group containing 2-10 carbon atoms; further preferably, R1 and R2 each independently represent a straight chain or branched alkyl group containing 1-8 carbon atoms, a straight chain or branched alkoxy group containing 1-7 carbon atoms, or a straight chain or branched alkenyl group containing 2-8 carbon atoms.

[0047] In some embodiments of the present invention, the compound of formula I is selected from the group consisting of:

[0048]

[0049]

[0050] as well as

[0051]

[0052] in,

[0053] R1' and R2' each independently represent a linear or branched alkyl group having 1 to 11 carbon atoms.

[0054] In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula I so that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, a larger absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0055] In some embodiments of the present invention, the weight percentage of the compound of formula I in the liquid crystal composition is 0.1%-30% (including all values ​​therebetween), for example, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30% or any range therebetween; preferably, in order to make the liquid crystal composition of the present invention have a larger VHR (UV), a larger absolute value of dielectric anisotropy and a smaller rotational viscosity, the weight percentage of the compound of formula I in the liquid crystal composition is preferably 10%-30%.

[0056] In some embodiments of the present invention, in order to obtain a larger VHR(UV), an appropriate absolute value of dielectric anisotropy, and maintain a smaller rotational viscosity, the liquid crystal composition of the present invention preferably comprises at least three compounds of Formula I.

[0057] In some embodiments of the present invention, in order to make the liquid crystal composition of the present invention have a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial), preferably, the compound of general formula I is selected from the group consisting of compounds of general formula I-1, compounds of general formula I-4 and compounds of general formula I-6; further preferably, the compound of general formula I is selected from the group consisting of compounds of general formula I-4 and compounds of general formula I-6; particularly preferably, the compound of general formula I contains at least one compound of general formula I-6.

[0058] In some embodiments of the present invention, the compound of formula II is selected from the group consisting of:

[0059]

[0060]

[0061] as well as

[0062]

[0063] In some embodiments of the present invention, 0≤n1+n2≤1; preferably, n2 represents 0.

[0064] In some embodiments of the present invention, it is preferred to adjust the content of the compound of general formula II so that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0065] In some embodiments of the present invention, the weight percentage of the compound of formula II in the liquid crystal composition is 0.1%-50% (including all values ​​therebetween), for example, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 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%, 100%, 100%, 101%, 102%, 103%, 104%, 105%, 10 34%, 35%, 36%, 38%, 40%, 42%, 44%, 45%, 46%, 48%, 50% or any range therebetween; preferably, in order to enable the liquid crystal composition of the present invention to obtain an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy and a smaller rotational viscosity, the weight percentage of the compound of formula II in the liquid crystal composition is 10%-50%; more preferably 30%-50%.

[0066] In some embodiments of the present invention, in order to take into account appropriate clearing points, appropriate optical anisotropy, appropriate absolute values ​​of dielectric anisotropy and smaller rotational viscosity, the liquid crystal composition of the present invention contains at least three compounds of general formula II; preferably, the liquid crystal composition of the present invention contains at least three compounds of general formula II accounting for 10%-50% by weight of the liquid crystal composition.

[0067] In some embodiments of the present invention, in order to make the liquid crystal composition of the present invention have an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, an appropriate VHR (initial), a smaller rotational viscosity and a higher VHR (UV), preferably, the compound of general formula II is selected from the group consisting of compounds of general formula II-1 and compounds of general formula II-4; in order to further make the liquid crystal composition of the present invention take into account an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy and a smaller rotational viscosity, preferably, the mass percentage of the compound of general formula II-4 in the liquid crystal composition is 3%-30% (including all values ​​therebetween) (for example, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 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%, 3%, 24%, 25%, 26%, 27%, 28%, 29%, 30% or any range between any two thereof); further preferably, the mass percentage of the compound of formula II-4 in the liquid crystal composition is 10%-30% (including all values ​​therebetween) (for example, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30% or any range therebetween); further preferably, 15%-30% (including all values ​​therebetween) (for example, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30% or any range therebetween).

[0068] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of the general formula N:

[0069]

[0070] in,

[0071] R N1 and R N2each independently represents 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, One or more non-adjacent -CH2- in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-;

[0072] ring and ring Each independently expresses in One or more -CH2- in may be replaced by -O-, wherein One or more -H in the ring may be independently replaced by -F, -Cl or -CN, and one or more -CH= in the ring may be replaced by -N=;

[0073] Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-;

[0074] L N1 and L N2 Each independently represents -H, an alkyl group containing 1 to 3 (e.g., 1, 2, 3) carbon atoms, or a halogen;

[0075] n N1 Represents 0, 1, 2, or 3, n N2 Represents 0 or 1, and 0≤n N1 +n N2 ≤3, where n N1 =2 or 3, the ring Can be the same or different, Z N1 may be the same or different; and

[0076] When n N1 +n N2 =1, the compound of the general formula N does not contain a biphenyl structure.

[0077] In some embodiments of the present invention, L N1 and L N2 All represent -H.

[0078] In some embodiments of the present invention, the compound of formula N is selected from the group consisting of:

[0079]

[0080]

[0081] as well as

[0082]

[0083] In some embodiments of the present invention, when it is necessary to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, the lower limit of the content of the compound of the general formula N is preferably low, and the upper limit is preferably low; further, when it is necessary to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability good, the lower limit of the content of the compound of the general formula N is preferably low, and the upper limit is preferably low; in addition, in order to keep the driving voltage low and increase the absolute value of the dielectric anisotropy, it is preferred to make the lower limit of the content of the compound of the general formula N higher, and the upper limit is higher.

[0084] In some embodiments of the present invention, preferably, R N1 and R N2 Each independently represents a straight chain or branched alkyl group containing 1 to 10 carbon atoms, a straight chain or branched alkoxy group containing 1 to 9 carbon atoms, or a straight chain or branched alkenyl group containing 2 to 10 carbon atoms; further preferably, R N1 and R N2 Each independently represents a straight chain or branched chain alkyl group containing 1 to 8 carbon atoms, a straight chain or branched chain alkoxy group containing 1 to 7 carbon atoms, or a straight chain or branched chain alkenyl group containing 2 to 8 carbon atoms.

[0085] In some embodiments of the present invention, in order to make the liquid crystal composition of the present invention have a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial), preferably, the compound of general formula N is selected from the group consisting of compounds of general formula N-2, compounds of general formula N-7, general formula N-15 and compounds of general formula N-22.

[0086] In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula N so that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0087] 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%-40% (including all values ​​in between), for example, 0.1%, 1%, 4%, 5%, 6%, 8%, 10%, 11%, 12%, 14%, 16%, 18%, 19%, 20%, 22%, 23%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40% or any range between two of them.

[0088] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of the general formula M:

[0089]

[0090] in,

[0091] R M1 and R M2 each independently represents a straight 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, One or more non-adjacent -CH2- in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-;

[0092] ring ring and ring Each independently expresses in 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, wherein At most one -H in may be replaced by halogen;

[0093] Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -C≡C-, -CH=CH-, -CH2CH2- or -(CH2)4-; and

[0094] n M represents 0, 1, or 2, where n M =2, ring Can be the same or different, Z M2 Can be the same or different.

[0095] In some embodiments of the present invention, preferably, R M1 and R M2Each independently represents a straight chain or branched alkyl group containing 1 to 10 carbon atoms, a straight chain or branched alkoxy group containing 1 to 9 carbon atoms, or a straight chain or branched alkenyl group containing 2 to 10 carbon atoms; further preferably, R M1 and R M2 Each independently represents a straight chain or branched chain alkyl group containing 1 to 8 carbon atoms, a straight chain or branched chain alkoxy group containing 1 to 7 carbon atoms, or a straight chain or branched chain alkenyl group containing 2 to 8 carbon atoms.

[0096] In some embodiments of the present invention, preferably, R M1 and R M2 Each independently represents a straight chain alkenyl group containing 2 to 8 carbon atoms; further preferably, R M1 and R M2 Each independently represents a straight chain alkenyl group containing 2 to 5 carbon atoms.

[0097] In some embodiments of the present invention, preferably, R M1 and R M2 One of them is a straight chain alkenyl group having 2 to 5 carbon atoms, and the other is a straight chain alkyl group having 1 to 5 carbon atoms.

[0098] In some embodiments of the present invention, preferably, R M1 and R M2 Each independently represents a straight chain alkoxy group containing 1 to 8 carbon atoms; further preferably, R M1 and R M2 Each independently represents a straight-chain alkoxy group containing 1 to 5 carbon atoms.

[0099] In some embodiments of the present invention, preferably, R M1 and R M2 One of them is a straight-chain alkoxy group having 1 to 5 carbon atoms, and the other is a straight-chain alkyl group having 1 to 5 carbon atoms.

[0100] In some embodiments of the present invention, when reliability is important, R M1 and R M2 are all alkyl groups; when it is important to reduce the volatility of the compound, R M1 and R M2 are all alkoxy groups; when the viscosity reduction is important, R M1 and R M2 At least one of them is alkenyl.

[0101] As used herein, the term "containing 1-r carbon atoms" (wherein r is an integer greater than 1) may mean containing any integer between 1 and r (including the end values ​​1 and r) carbon atoms, for example, containing 2 carbon atoms, containing (r-1) carbon atoms, or containing r carbon atoms. For example, "containing 1-12 carbon atoms" may mean containing 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0102] As used herein, the term "integer of y1-y2" can be any integer between the range (including the end values ​​y1 and y2). For example, "integer of 0-12" can be, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0103] The alkenyl group in the present invention is preferably selected from the group represented by any one of formula (V1) to formula (V9), and is particularly preferably formula (V1), formula (V2), formula (V8) or (V9). The groups represented by formula (V1) to formula (V9) are as follows:

[0104]

[0105]

[0106] Wherein, * indicates the connection site in the bonded ring structure.

[0107] The alkenyloxy group in the present invention is preferably selected from the group represented by any one of formula (OV1) to formula (OV9), and is particularly preferably the group represented by formula (OV1), formula (OV2), formula (OV8) or formula (OV9). The groups represented by formula (OV1) to formula (OV9) are as follows:

[0108]

[0109] Wherein, * indicates the connection site in the bonded ring structure.

[0110] In some embodiments of the present invention, the compound of formula M is selected from the group consisting of:

[0111]

[0112]

[0113] as well as

[0114]

[0115] In some embodiments of the present invention, in order to make the liquid crystal composition of the present invention have a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial), 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-11 and compounds of general formula M-13.

[0116] In some embodiments of the present invention, the content of the compound of formula M must be appropriately adjusted according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drip marks, screen burn-in, dielectric anisotropy, etc.

[0117] Regarding the content of the compound of general formula M, when it is necessary to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, the lower limit is preferably higher and the upper limit is higher; further, when it is necessary to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability good, the lower limit is preferably higher and the upper limit is higher; in order to keep the driving voltage low and increase the absolute value of the dielectric anisotropy, the lower limit is preferably lower and the upper limit is lower.

[0118] In some embodiments of the present invention, it is preferred to adjust the content of the compound of general formula M so that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial).

[0119] 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%-60% (including all values ​​in between), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 47.5%, 48%, 50%, 52%, 53.5%, 54%, 56%, 58%, 60% or any range of values ​​between two of them.

[0120] 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 formula A-1 and formula A-2:

[0121]

[0122] in,

[0123] R A1 and R A2 each independently represents 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, wherein one or more non-adjacent -CH2- in a straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and wherein a straight-chain or branched alkyl group containing 1 to 12 carbon atoms, One or more -H in can be independently replaced by -F or -Cl;

[0124] ring ring ring and ring Each independently expresses in 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, wherein One or more -H in the ring may be independently replaced by -F, -Cl or -CN, and one or more -CH= in the ring may be replaced by -N=;

[0125] 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-, -CH2O- or -OCH2-;

[0126] 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;

[0127] X A1 and X A2 Each independently represents halogen, a straight-chain or branched haloalkyl or haloalkoxy group containing 1 to 5 carbon atoms, or a straight-chain or branched haloalkenyl or haloalkenoxy group containing 2 to 5 carbon atoms;

[0128] n A11 represents 0, 1, 2, or 3, where n A11 =2 or 3, the ring Can be the same or different, Z A11Can be the same or different;

[0129] n A12 represents 1 or 2, where n A12 =2, ring may be the same or different; and

[0130] n A2 represents 0, 1, 2, or 3, where n A2 =2 or 3, the ring Can be the same or different, Z A21 Can be the same or different.

[0131] In some embodiments of the present invention, the weight percentage of the compound selected from the group consisting of the compound of general formula A-1 and the compound of general formula A-2 in the liquid crystal composition is 0.1%-60% (including all values ​​in between), 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 numerical range between any two of them.

[0132] In some embodiments of the present invention, the compound of formula A-1 is selected from the group consisting of:

[0133]

[0134]

[0135]

[0136] as well as

[0137]

[0138] in,

[0139] R A1 represents a straight or branched alkyl group containing 1 to 8 carbon atoms, wherein one or more non-adjacent -CH2- in a straight or branched alkyl group containing 1 to 8 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H present in these groups may be independently replaced by -F or -Cl;

[0140] R v and R wEach independently represents -CH2- or -O-;

[0141] L A11 , L A12 , L A11 ', L A12 ', L A14 , L A15 and L A16 Each independently represents -H or -F;

[0142] L A13 and L A13 'Each independently represents -H or -CH3;

[0143] X A1 represents -F, -CF3 or -OCF3; and

[0144] v and w each independently represent 0 or 1.

[0145] 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%-50% (including all values ​​in between), 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 any range of values ​​between two of them.

[0146] 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 kept low and the response speed is fast, it is preferred to make its lower limit value slightly lower and the upper limit value slightly lower; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferred to make its lower limit value slightly lower and the upper limit value slightly lower; in addition, in order to keep the driving voltage low and increase the absolute value of dielectric anisotropy, it is preferred to make its lower limit value slightly higher and the upper limit value slightly higher.

[0147] In some embodiments of the present invention, the compound of formula A-2 is selected from the group consisting of:

[0148]

[0149]

[0150] as well as

[0151]

[0152] in,

[0153] R A2 represents a straight-chain or branched alkyl group containing 1 to 8 carbon atoms, wherein one or more non-adjacent -CH2- in the straight-chain or branched alkyl group containing 1 to 8 carbon atoms may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H present in these groups may be independently replaced by -F or -Cl;

[0154] L A21 , L A22 , L A23 , L A24 and L A25 each independently represents -H or -F; and

[0155] X A2 It represents -F, -CF3, -OCF3 or -CH2CH2CH=CF2.

[0156] 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%-50% (including all values ​​in between), 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 any range of values ​​between two of them.

[0157] 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 kept low and the response speed is fast, it is preferred to make its lower limit value slightly lower and the upper limit value slightly lower; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferred to make its lower limit value slightly lower and the upper limit value slightly lower; in addition, in order to keep the driving voltage low and increase the absolute value of the dielectric anisotropy, it is preferred to make its lower limit value slightly higher and the upper limit value slightly higher.

[0158] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of formula B:

[0159]

[0160] in,

[0161] R B1 and R B2Each independently represents halogen, -CF3, -OCF3, 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, A straight or branched alkyl group containing 1 to 12 carbon atoms, One or more non-adjacent -CH2- can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-;

[0162] ring and ring Each independently expresses in 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, wherein One or more -H in the ring may be independently replaced by -CN, -F or -Cl, and one or more -CH= in the ring may be replaced by -N=;

[0163] X B represents -O-, -S-, or -CO-;

[0164] L B1 and L B2 Each independently represents -H, -F, -Cl, -CF3 or -OCF3;

[0165] Z B1 and Z B2 Each independently represents a single bond, -O-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-; and

[0166] n B1 and n B2 Each independently represents 0, 1 or 2, where n B1 When it indicates 2, the ring can be the same or different, where n B2 When it indicates 2, the ring Can be the same or different, Z B2 Can be the same or different.

[0167] In some embodiments of the present invention, the compound of formula B is selected from the group consisting of:

[0168]

[0169] as well as

[0170]

[0171] in,

[0172] R B1 ' and R B2 ' Each independently represents a straight or branched alkyl group containing 1 to 11 carbon atoms.

[0173] In some embodiments of the present invention, the weight percentage of the compound of general formula B in the liquid crystal composition is 0.1%-30% (including all values ​​therebetween), for example, 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30% or a numerical range between any two of them.

[0174] In some embodiments of the present invention, the liquid crystal composition further comprises at least one polymerizable compound of the general formula RM:

[0175]

[0176] in,

[0177] R5 represents -H, halogen, -CN, -Sp2-P2, 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, A straight or branched alkyl group containing 1 to 12 carbon atoms, One or more non-adjacent -CH2- may be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H may be independently replaced by -F or -Cl;

[0178] ring and ring Each independently expresses in 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, wherein One or more -H in the -H can be independently replaced by -F, -Cl, -CN, -Sp3, -P3, a halogenated or unhalogenated straight-chain alkyl group containing 1-12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms, a halogenated or unhalogenated straight-chain alkoxy group containing 1-11 carbon atoms, substituted, and -CH= in one or more rings may be replaced by -N=;

[0179] ring express in One or more -H in the -H can be independently replaced by -F, -Cl, -CN, -Sp3, -P3, a halogenated or unhalogenated straight-chain alkyl group containing 1-12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms, a halogenated or unhalogenated straight-chain alkoxy group containing 1-11 carbon atoms, substituted, and -CH= in one or more rings may be replaced by -N=;

[0180] P1, P2 and P3 each independently represent a polymerizable group;

[0181] Sp1, Sp2 and Sp3 each independently represent a spacer group or a single bond;

[0182] Z1 and Z2 each independently represent -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH2O-, -OCH2-, -CH2S-, -SCH2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) 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, where R 1 and R 2 Each independently represents a straight 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, and d represents an integer of 1 to 4; X0 represents -O-, -S-, -CO-, -CF2-, -NH- or -NF-; and a represents 0, 1 or 2, b represents 0 or 1, wherein when a represents 2, the ring can be the same or different, and Z1 can be the same or different.

[0183] In some embodiments of the present invention, the compound of formula RM is selected from the group consisting of:

[0184]

[0185]

[0186]

[0187]

[0188] as well as

[0189]

[0190] in,

[0191] X1-X 10 and X 12 Each independently represents -F, -Cl, -Sp3-P3, a linear alkyl or alkoxy group containing 1 to 5 carbon atoms,

[0192] The polymerizable groups involved in the present invention are groups suitable for polymerization reactions (e.g., free radical or ionic polymerization, addition polymerization or condensation polymerization), or groups suitable for addition or condensation on the polymer backbone. For chain polymerization, polymerizable groups containing -CH=CH- or -C≡C- are particularly preferred, and for ring-opening polymerization, for example, oxetane or epoxy groups are particularly preferred.

[0193] In some embodiments of the present invention, the polymerizable groups P1, P2 and P3 each independently represent or -SH; Preferably, the polymerizable groups P1, P2 and P3 each independently represent or -SH; Further preferably, the polymerizable groups P1, P2 and P3 each independently represent

[0194] As used herein, the term "spacer group" is known to those skilled in the art and is 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 the mesogenic group and the polymerizable group in a polymerizable compound. Typical spacer groups are, for example, -(CH2)p1-, -(CH2CH2O)q1-CH2CH2-, -(CH2CH2S)q1-CH2CH2-, -(CH2CH2NH)q1-CH2CH2-, -CR 0 R 00 -(CH2)p1- or -(SiR 0 R00 -O)p1-, wherein p1 represents an integer from 1 to 12, q1 represents an integer from 1 to 3, and R 0 and R 00 Each independently represents -H, a straight 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-.

[0195] In some embodiments of the present invention, the weight percentage of the polymerizable compound of the general formula RM in the liquid crystal composition is 0.001%-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%, 0.1%, 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 any range between two of them.

[0196] In some embodiments of the present invention, the liquid crystal composition further comprises at least one additive.

[0197] In addition to the above compounds, the liquid crystal composition of the present invention may also contain conventional nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, dopants, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers or light stabilizers.

[0198] Possible dopants which are preferably added to the liquid crystal composition according to the invention are shown below:

[0199]

[0200]

[0201] as well as

[0202]

[0203] In some embodiments of the present invention, the weight percentage of the dopant in the liquid crystal composition is 0%-5%; preferably, the weight percentage of the dopant in the liquid crystal composition is 0.01%-1%.

[0204] In addition, the antioxidant, light stabilizer, ultraviolet absorber and other additives used in the liquid crystal composition of the present invention are preferably the following:

[0205]

[0206]

[0207]

[0208] Here, n represents a positive integer from 1 to 12.

[0209] Preferably, the antioxidant is selected from the compounds shown below:

[0210]

[0211] In some embodiments of the present invention, the light stabilizer accounts for 0%-5% of the total weight of the liquid crystal composition; preferably, the light stabilizer accounts for 0.01%-1% of the total weight of the liquid crystal composition.

[0212] Even in the absence of a polymerization initiator, the liquid crystal composition containing a polymerizable compound of the present invention can be polymerized, but in order to promote polymerization, a polymerization initiator may be further contained therein. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.

[0213] For the polymerization method of the polymerizable compound, since it is expected that the polymerization proceeds quickly, a method of polymerization by irradiation with active energy lines such as ultraviolet rays or electron beams is preferred. When using ultraviolet rays, a polarized light source can be used, or a non-polarized light source can be used. In addition, when the liquid crystal composition is polymerized in a state where it is clamped between two substrates, at least the substrate on the irradiated side must have appropriate transparency relative to the active energy line. In addition, a mask can be used during light irradiation to polymerize only a specific part, and then, by changing conditions such as the electric field, magnetic field or temperature, the orientation state of the unpolymerized part is changed, and further irradiation with active energy lines is performed for polymerization. In particular, when ultraviolet exposure is performed, it is preferred to perform ultraviolet exposure while applying a voltage to the liquid crystal composition.

[0214] The temperature during irradiation with active energy rays such as ultraviolet rays or electron beams is preferably within a temperature range that maintains the liquid crystal state of the liquid crystal composition of the present invention. Polymerization is preferably carried out at a temperature close to room temperature (i.e., 15-35°C). As for the lamp that generates ultraviolet rays, metal halide lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, etc. can be used. In addition, as for the wavelength of the irradiated ultraviolet rays, it is preferred to irradiate ultraviolet rays with a wavelength outside the absorption wavelength region of the liquid crystal composition, and it is preferred to use ultraviolet rays that are blocked as needed. The intensity of the irradiated ultraviolet rays is preferably 0.1mW / cm 2 -50mW / cm 2 When irradiating ultraviolet rays, the intensity can be changed, and the time of irradiating ultraviolet rays can be appropriately selected according to the intensity of the irradiated ultraviolet rays, preferably 10s-600s.

[0215] As used herein, the terms "tilt" and "tilt angle" are to be understood as the tilted alignment of liquid crystal molecules relative to the surface of a liquid crystal cell in a liquid crystal display device (preferably a VA, IPS or FFS type liquid crystal display device in the present invention). The tilt angle represents the average angle (<90°) formed between the longitudinal molecular axes (liquid crystal director) of the liquid crystal molecules and the surface of the outer plate of the liquid crystal cell. A low value of the tilt angle (i.e., a large angle deviating from 90°) corresponds to a large tilt.

[0216] In yet another aspect, the present invention further provides a liquid crystal display device comprising the liquid crystal composition.

[0217] In some embodiments of the present invention, the liquid crystal composition is particularly suitable for use in VA, IPS or FFS type display devices.

[0218] Beneficial effects: Compared with the prior art, the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial), so that the liquid crystal display device containing it has a faster response speed, better low-temperature stability and higher reliability. DETAILED DESCRIPTION

[0219] The present invention will be described below in conjunction with specific embodiments. It should be noted that the following embodiments are examples of the present invention and are only used to illustrate the present invention, but not to limit the present invention. Other combinations and various modifications within the concept of the present invention may be performed without departing from the spirit or scope of the present invention.

[0220] In the present invention, unless otherwise specified, the contents are expressed in percentage by weight.

[0221] For ease of expression, in the following examples, the group structure of each compound is represented by the code listed in Table 2:

[0222] Table 2. Group structure codes of compounds

[0223]

[0224]

[0225] Take the following compound as an example:

[0226]

[0227] If the structural formula is represented by the codes listed in Table 2, it can be expressed as: nCCGF, where n in the code represents the number of C atoms in the left-hand alkyl group, for example, n is "3", which means that the alkyl group is -C3H7; C in the code represents 1,4-cyclohexylene, G represents 2-fluoro-1,4-phenylene, and F represents a fluorine substituent.

[0228] The abbreviated codes for the test items in the following embodiments are as follows:

[0229] Cp clearing point (nematic-isotropic phase transition temperature, °C)

[0230] Δn optical anisotropy (589nm, 20℃)

[0231] Δε Dielectric anisotropy (1KHz, 20℃)

[0232] VHR(initial) Initial voltage holding rate (%)

[0233] VHR(UV) Voltage holding ratio after ultraviolet (UV) irradiation (%)

[0234] t -30℃ Low temperature storage time (days, -30℃)

[0235] γ1 Rotational viscosity (mPa·s, 20℃)

[0236] PTA1 Pre-tilt angle formed after ultraviolet light (UV1) irradiation (°, 20°C)

[0237] in,

[0238] Cp: ​​obtained by melting point test.

[0239] Δn: measured using an Abbe refractometer under a sodium lamp (589 nm) at 20°C.

[0240] Δε:Δε=ε || -ε ⊥ , where ε || is the dielectric constant parallel to the molecular axis, ε ⊥is the dielectric constant perpendicular to the molecular axis; test conditions: 20°C, 1KHz, VA type test box with a box thickness of 6μm.

[0241] VHR(initial): initial voltage holding rate, tested using TOY06254 liquid crystal property evaluation system; test temperature is 60°C, test voltage is 5V, test frequency is 6Hz, and the cell thickness is 9μm TN type test cell.

[0242] VHR (UV) is measured using the TOY06254 liquid crystal property evaluation system; the wavelength used is 365nm and the energy is 6000mJ / cm 2 The test was conducted after the liquid crystal was irradiated with UV light, the test temperature was 60°C, the test voltage was 5V, the test frequency was 6Hz, and the cell thickness was 9μm in a TN type test cell.

[0243] t -30℃ : The nematic liquid crystal medium is placed in a glass bottle and stored at -30°C, and the time is recorded when crystal precipitation is observed.

[0244] γ1: obtained by testing using LCM-2 liquid crystal property evaluation system; test conditions: 20°C, 160-240V, test box thickness 20μm.

[0245] PTA1: PTA was tested using the crystal rotation method. Liquid crystal was poured into a VA-type test box (box thickness: 3.5 μm), voltage was applied (15 V, 60 Hz), and ultraviolet light UV1 was used for 90 seconds to polymerize the polymerizable compound to form a pre-tilt angle PTA1.

[0246] Each component used in the following examples can be synthesized by a known method or obtained through commercial channels. These synthesis techniques are conventional, and each liquid crystal compound obtained meets the standards of electronic compounds after testing.

[0247] Liquid crystal compositions are prepared according to the ratios of the liquid crystal compositions specified in the following examples. The preparation of the liquid crystal compositions is carried out according to conventional methods in the art, such as mixing in proportion by heating, ultrasonic waves, suspension, etc.

[0248] Comparative Example 1

[0249] The liquid crystal composition of Comparative Example 1 was prepared according to the compounds and their weight percentages listed in Table 3, and filled between two substrates of a liquid crystal display for performance testing.

[0250] Table 3. Liquid crystal composition formula and performance parameter test results

[0251]

[0252]

[0253] Example 1

[0254] The liquid crystal composition of Example 1 was prepared according to the compounds and their weight percentages listed in Table 4, and filled between two substrates of a liquid crystal display for performance testing.

[0255] Table 4. Liquid crystal composition formula and performance parameter test results

[0256]

[0257] From the comparison between Comparative Example 1 and Example 1, it can be seen that the liquid crystal composition of the present invention has a smaller rotational viscosity and a higher VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy and an appropriate VHR (initial).

[0258] Example 2

[0259] The liquid crystal composition of Example 2 was prepared according to the compounds and their weight percentages listed in Table 5, and filled between two substrates of a liquid crystal display for performance testing.

[0260] Table 5. Liquid crystal composition formula and performance parameter test results

[0261]

[0262]

[0263] Example 3

[0264] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 6, and 0.3% by weight of It was added to the liquid crystal composition shown in Table 6 as Example 3, and filled between two substrates of a liquid crystal display for performance testing.

[0265] Table 6. Liquid crystal composition formula and performance parameter test results

[0266]

[0267] Example 4

[0268] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 7. It was added to the liquid crystal composition shown in Table 7 as Example 4, and filled between two substrates of a liquid crystal display for performance testing.

[0269] Table 7 Formulation and performance parameter test results of liquid crystal composition

[0270]

[0271] Example 5

[0272] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 8, and 0.3% by weight of It was added to the liquid crystal composition shown in Table 8 as Example 5, and filled between two substrates of a liquid crystal display for performance testing.

[0273] Table 8. Liquid crystal composition formula and performance parameter test results

[0274]

[0275]

[0276] Example 6

[0277] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 9, and 0.3% by weight of It was added to the liquid crystal composition shown in Table 9 as Example 6, and filled between two substrates of a liquid crystal display for performance testing.

[0278] Table 9. Liquid crystal composition formula and performance parameter test results

[0279]

[0280] Example 7

[0281] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 10, and 0.3% by weight of It was added to the liquid crystal composition shown in Table 10 as Example 7, and filled between two substrates of a liquid crystal display for performance testing.

[0282] Table 10. Liquid crystal composition formulation and performance parameter test results

[0283]

[0284]

[0285] Example 8

[0286] Liquid crystal compositions were prepared according to the compounds and their weight percentages listed in Table 11, and 0.3% by weight of It was added to the liquid crystal composition shown in Table 11 as Example 8, and filled between two substrates of a liquid crystal display for performance testing.

[0287] Table 11. Liquid crystal composition formula and performance parameter test results

[0288]

[0289] Example 9

[0290] Adding 0.3% of the polymerizable compound of RM-1-1 into the liquid crystal composition in Example 2 can achieve polymerization with a faster angular velocity and form a smaller pre-tilt angle, PTA1=1.5°.

[0291]

[0292] In summary, the liquid crystal composition of the present invention has a small rotational viscosity and a high VHR (UV) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, and an appropriate VHR (initial), so that the liquid crystal display device containing it has a faster response speed, better low temperature stability and higher reliability. And when the dielectric anisotropy of the present application is increased by 34%, the rotational viscosity is only sacrificed by up to 25% (summarized by comparing Example 8 and Comparative Example 1), that is, the liquid crystal composition of the present application, through the coordination of various components, makes the liquid crystal composition of the present invention take into account the appropriate clearing point, appropriate optical anisotropy, appropriate absolute value of dielectric anisotropy, appropriate VHR (initial), small rotational viscosity and high VHR (UV) at the same time.

[0293] The above implementation modes are only for illustrating the technical concept and features of the present invention, and their purpose is to enable people familiar with this technology to understand the content of the present invention and implement it, and they cannot be used to limit the protection scope of the present invention. Any equivalent changes or modifications made according to the spirit of the present invention should be included in the protection scope of the present invention.

Claims

1. A liquid crystal composition, comprising at least one compound of formula F, wherein the compound of formula F is selected from the group consisting of the following compounds: and At least one compound of the general formula I and at least one compound of the general formula II: as well as in, R F1 represents -H, halogen, a straight or branched alkyl group containing 1 to 12 carbon atoms, wherein one or more non-adjacent -CH2- in the straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H in the straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -F or -Cl; R1, R2, R3 and R4 each independently represent a straight or branched alkyl group containing 1 to 12 carbon atoms, wherein one or more non-adjacent -CH2- in the straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; ring express X F1 and X F2 Each independently represents -CH2- or -O-; L1 and L2 each independently represent -H, -F, -Cl, -CF3 or -OCF3; L3, L4, L5 and L6 each independently represent -F, -Cl, -CF3 or -OCF3; Z F1 and Z F2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-; n1 and n2 each independently represent 0 or 1; and The weight percentage of the compound of general formula F in the liquid crystal composition is 0.1%-8%; the weight percentage of the compound of general formula II in the liquid crystal composition is 0.1%-50%.

2. The liquid crystal composition according to claim 1, characterized in that: The compound of formula I is selected from the group consisting of the following compounds: as well as in, R1' and R2' each independently represent a linear or branched alkyl group having 1 to 11 carbon atoms.

3. The liquid crystal composition according to claim 1, characterized in that: The compound of formula II is selected from the group consisting of the following compounds: as well as 4. The liquid crystal composition according to claim 1, characterized in that: The liquid crystal composition further comprises at least one compound of the general formula N: in, R N1 and R N2 Each independently represents a straight or branched alkyl group containing 1 to 12 carbon atoms, wherein one or more non-adjacent -CH2- in the straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; ring and ring Each independently expresses in One or more -CH2- in can be replaced by -O-, wherein One or more -H in the ring can be independently replaced by -F, -Cl or -CN, and one or more -CH= in the ring can be replaced by -N=; Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-; L N1 and L N2 Each independently represents -H, an alkyl group containing 1 to 3 carbon atoms or a halogen; n N1 Indicates 0, 1, 2, or 3, n N2 Represents 0 or 1, and 0≤n N1 +n N2 ≤3, where n N1 =2 or 3, the ring Same or different, Z N1 the same or different; and When n N1 +n N2 =1, the compound of the general formula N does not contain a biphenyl structure.

5. The liquid crystal composition according to claim 4, characterized in that: The compound of formula N is selected from the group consisting of the following compounds: as well as 6. The liquid crystal composition according to claim 4, characterized in that: The liquid crystal composition further comprises at least one compound of the general formula M: in, R M1 and R M2 Each independently represents a straight or branched alkyl group containing 1 to 12 carbon atoms, wherein one or more non-adjacent -CH2- in the straight-chain or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; ring ring and ring Each independently expresses in One or more -CH2- in the ring can be replaced by -O-, and one or more single bonds in the ring can be replaced by double bonds, wherein At most one -H in can be replaced by a halogen; Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -C≡C-, -CH=CH-, -CH2CH2- or -(CH2)4-; and n M represents 0, 1, or 2, where n M =2, ring Same or different, Z M2 Same or different.

7. The liquid crystal composition according to claim 6, characterized in that: The compound of formula M is selected from the group consisting of the following compounds: as well as 8. The liquid crystal composition according to claim 1, characterized in that: The liquid crystal composition further comprises at least one polymerizable compound of the general formula RM: in, R5 represents -H, halogen, -CN, -Sp2-P2, a straight or branched alkyl group containing 1 to 12 carbon atoms, wherein the straight or branched alkyl group containing 1 to 12 carbon atoms, One or more non-adjacent -CH2- can be independently replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H can be independently replaced by -F or -Cl; ring and ring Each independently expresses in One or more -CH2- in the ring can be replaced by -O-, and one or more single bonds in the ring can be replaced by double bonds, wherein One or more -H in the -H can be independently replaced by -F, -Cl, -CN, -Sp3-P3, a halogenated or unhalogenated straight-chain alkyl group containing 1 to 12 carbon atoms, a halogenated or unhalogenated straight-chain alkoxy group containing 1 to 11 carbon atoms, Substitution, and one or more ring -CH= can be replaced by -N=; ring express in One or more -H in the -H can be independently replaced by -F, -Cl, -CN, -Sp3-P3, a halogenated or unhalogenated straight-chain alkyl group containing 1 to 12 carbon atoms, a halogenated or unhalogenated straight-chain alkoxy group containing 1 to 11 carbon atoms, Substitution, and one or more ring -CH= can 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-, -CH2O-, -OCH2-, -CH2S-, -SCH2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) 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, where R 1 and R 2 Each independently represents a straight or branched alkyl group containing 1 to 12 carbon atoms, and d represents an integer of 1 to 4; X0 represents -O-, -S-, -CO-, -CF2-, -NH- or -NF-; and a represents 0, 1 or 2, b represents 0 or 1, wherein when a represents 2, the ring The same or different, Z1 the same or different.

9. The liquid crystal composition according to claim 6, characterized in that: The weight percentage of the compound of general formula I in the liquid crystal composition is 0.1%-30%; the weight percentage of the compound of general formula N in the liquid crystal composition is 0.1%-40%; the weight percentage of the compound of general formula M in the liquid crystal composition is 0.1%-60%.

10. The liquid crystal composition according to claim 1, characterized in that: The liquid crystal composition further comprises at least one additive.

11. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 10.

Citation Information

Patent Citations

  • Liquid crystal medium

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  • Cycloalkyl-containing dibenzofuran derivative liquid crystal compound and applications thereof

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    CN1942461A

  • fluorinated aromatics and their use in liquid crystal mixtures

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