Liquid crystal composition and liquid crystal display device comprising same
By combining compounds containing cyclohexene and dibenzo pentacyclic structures in the liquid crystal composition, the performance of the liquid crystal material is optimized, the balance of high contrast and fast response speed is solved, and the display effect and stability of the liquid crystal display are improved, especially in the IPS liquid crystal display mode.
Patent Information
- Application Number
- PCT/CN2024/140001
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-12-29
- Filing Date
- 2024-12-17
- Publication Date
- 2025-07-03
AI Technical Summary
Existing liquid crystal display materials are difficult to balance between high contrast and fast response speed, especially the Flicker scintillation value and low temperature mutual solubility are insufficient, which affects the display quality and stability.
By combining cyclohexene-containing compounds with dibenzopentacyclic structures in the liquid crystal composition, the composition and structural design are optimized to improve dielectric anisotropy, optical anisotropy, elastic constant and rotational viscosity, and improve Flicker scintillation value and low temperature mutual solubility.
It achieves the balance between high contrast and fast response speed of liquid crystal materials, improves the display effect of LCD display, reduces Flicker flicker value and improves low temperature stability, and is suitable for high contrast and fast response IPS LCD display mode.
Smart Images

Figure CN2024140001_03072025_PF_FP_ABST
Abstract
Description
Liquid crystal composition and liquid crystal display device containing the same Technical Field
[0001] The present application belongs to the technical field of liquid crystal materials, and specifically relates to a liquid crystal composition and a liquid crystal display device containing the same. Background Art
[0002] Liquid crystal material is a mixture of organic rod-shaped small molecular compounds that have both liquid fluidity and crystal anisotropy at a certain temperature. Liquid crystal display devices operate by utilizing the optical anisotropy and dielectric anisotropy of the liquid crystal material itself.
[0003] Compared to traditional display devices and materials, liquid crystal display materials offer significant advantages: low driving voltage, minimal power consumption, high reliability, large amounts of displayed information, color display, flicker-free display, no harmful effects on the human body, automated production processes, low cost, the ability to manufacture LCDs of various specifications and types, and portability. These advantages have profoundly impacted the display and imaging fields, promoting the development of microelectronics and optoelectronic information technologies. Liquid crystal materials, with their excellent optical properties and photoelectric effect, have found widespread application in numerous display applications.
[0004] However, with the widespread application of liquid crystal display materials, the requirements for their performance are also constantly increasing. Not only are the physical parameters of liquid crystal materials (such as dielectric anisotropy, optical anisotropy, and elastic constants) required to match the device requirements, and the liquid crystal materials have high stability (including high-temperature stability and chemical stability), but they are also required to have high-definition display image quality. High-definition display image quality requires faster response speed (the lower the rotational viscosity γ1, the better; the smaller the rotational viscosity, the faster the response speed) and less flicker. During the use of the liquid crystal panel, the polarity switching of the common electrode signal (Vcom) produces a flickering phenomenon of horizontal stripes, which is generally referred to as the Flicker phenomenon in the industry. Among them, the numerical value of the Flicker flicker value also directly reflects the quality and reliability of the liquid crystal panel. Generally, the larger the value of the Flicker flicker value, the more likely the liquid crystal panel will produce image sticking (IS), and vice versa, it will reduce / prevent image sticking. When the flicker phenomenon is severe, it will lead to increased image retention on the LCD panel, reduce display quality, and cause physiological discomfort to the viewer (such as eye fatigue, decreased vision, and dizziness). Therefore, during the production process of liquid crystal materials, it is necessary to detect their flicker value and control their flicker value within a predetermined range.
[0005] The contrast ratio of an LCD display is actually the ratio of brightness. More precisely, the contrast ratio is the value obtained by subtracting the saturation of the white signal at 100% and 0%, and then dividing it by the 0% white value (a 0% white signal is actually black) measured in Lux (illuminance, i.e., lumens per square meter). The contrast ratio is the division of the blackest and whitest brightness units. Therefore, the brighter the white and the darker the black, the higher the contrast ratio. Contrast ratio is a key parameter of LCD displays. At a reasonable brightness value, the higher the contrast ratio, the richer the color gradation it can display.
[0006] Compounds containing cyclohexene structures are a relatively new class of liquid crystal monomer materials that have emerged in recent years. They offer advantages such as fast response and large K values, and are typically used in negative, fast-response, high-contrast liquid crystal materials. However, when the content of a particular monomer type in a formulation is too high, it can affect performance such as low-temperature storage. Increasing the variety of cyclohexene compounds allows for the inclusion of a larger amount of these monomers in the formulation, improving low-temperature miscibility while also effectively increasing the K value of the formulation, thereby enhancing contrast and improving the flicker of the liquid crystal. A disadvantage of cyclohexene-containing compounds is their limited usage; excessive usage can easily lead to decreased miscibility, thus affecting performance such as low-temperature storage.
[0007] In order to solve the problems existing in the related art, the present application advocates the use of a compound containing a cyclohexene structure and a compound containing a dibenzopentacyclic structure. The obtained liquid crystal composition can maintain appropriate optical anisotropy and a higher absolute value of dielectric anisotropy, while taking into account the advantages of increasing the type and amount of cyclohexene compounds used, thereby improving the low-temperature miscibility while effectively improving the elastic constant of the liquid crystal composition, having a lower rotational viscosity, better contrast, transmittance, better Flicker flicker value, improving low-frequency display and response rate, and can be widely used in high-contrast and fast-response IPS liquid crystal display modes. Summary of the Invention
[0008] The following is a summary of the subject matter described in detail herein. This summary is not intended to limit the scope of the claims.
[0009] The present application provides a liquid crystal composition and a liquid crystal display device containing the same. The liquid crystal composition of the present application has appropriate optical anisotropy, a relatively high absolute value of dielectric anisotropy, an appropriate clearing point, a relatively large elastic constant, a relatively low rotational viscosity, a relatively good contrast ratio, and a relatively good Flicker value, effectively improving the response speed and enhancing the display effect of the liquid crystal material, and can be applied to a high-contrast, fast-response IPS liquid crystal display mode.
[0010] In a first aspect, the present application provides a liquid crystal composition comprising at least one compound represented by formula I and at least one compound represented by formula II:
[0011] as well as
[0012] Among them, 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, One or at least two non-adjacent -CH2- in the linear or branched alkyl group containing 1 to 12 carbon atoms can be independently replaced by -O-, -CO-, -CO-O-, -O-CO- or Replacement;
[0013] ring and Ring Each independently expresses Among them, at least one ring or ring for
[0014] R3 and R4 each independently represent -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, The straight or branched alkyl group containing 1 to 12 carbon atoms, One or at least two non-adjacent -CH2- in the group may be independently replaced by -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO-, and one or at least two -H in the group may be independently replaced by -F or -Cl;
[0015] Z1 and Z2 each independently represent a single bond, -O-, -S-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-;
[0016] Z3 represents a single bond, -O(CH2) a -or-S(CH2) a -; a represents an integer from 0 to 3, such as 0, 1, 2 or 3;
[0017] ring and Ring Each independently expresses described One or at least two -CH2- in the ring may be replaced by -O-, and one or at most two non-adjacent single bonds in the ring may be replaced by double bonds; One or at least two -H in the ring may be independently replaced by -F, -Cl, -CN, -CH3 or -OCH3, and -CH= in one or at least two rings may be replaced by -N=;
[0018] G represents -O-, -S-, -CF2-, -NH-, -NF- or -CO-;
[0019] X1 and X2 each independently represent -H, halogen, a halogenated or unhalogenated alkyl group containing 1 to 3 (e.g., 1, 2, or 3) carbon atoms, or a halogenated or unhalogenated alkoxy group containing 1 to 3 (e.g., 1, 2, or 3) carbon atoms;
[0020] n1 and n2 are each independently 0, 1 or 2; when n1 = 2, the ring Same or different, Z1 same or different; when n2=2, the ring The same or different, Z2 the same or different.
[0021] The present application provides a liquid crystal composition, which includes a compound of the general formula I containing a cyclohexene structure and a compound of the general formula II containing a dibenzopentacyclic structure. By designing and compounding the specific components and structures of the liquid crystal composition, the liquid crystal composition has appropriate optical anisotropy, a high absolute value of dielectric anisotropy, an appropriate clearing point, a large elastic constant, a low rotational viscosity, a good contrast ratio, and a good Flicker value, effectively improving the response speed, helping to enhance the display effect of the liquid crystal material, and can be applied to high-contrast, fast-response IPS liquid crystal display mode.
[0022] In the present application, the 2-12 carbon atoms can be 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.
[0023] The alkenyl group in the present application is preferably a group represented by any one of formula (V1) to formula (V9), particularly preferably formula (V1), formula (V2), formula (V8) or formula (V9); the groups represented by formula (V1) to formula (V9) are as follows:
[0024] Here, "X" represents a carbon atom in the ring structure to which it is bonded.
[0025] The alkenyloxy group in the present application is preferably a group represented by any one of Formula (OV1) to Formula (OV9), and is particularly preferably Formula (OV1), Formula (OV2), Formula (OV8) or Formula (OV9); the groups represented by Formula (OV1) to Formula (OV9) are as follows:
[0026] "X" represents a carbon atom in a ring structure to which it is bonded.
[0027] When n1=2, there are two These two They may have the same structure or different structures. For example, one may be Another one is When the application involves the expression "same or different", they all have the same meaning.
[0028] In the present application, “can be independently replaced by…” means that it can be replaced or not replaced, that is, replacement or not replacement falls within the scope of protection of the present application, and the same applies to “can be independently replaced by…”, and the positions of “replacement” and “replacement” can be arbitrary.
[0029] In this application, the short straight lines on one or both sides of the group structure represent access bonds, not methyl groups, e.g. The short straight line on the left, Short straight lines on both sides.
[0030] In the present application, the halogen includes fluorine, chlorine, bromine or iodine, etc.; when the same description is mentioned below, they all have the same meaning.
[0031] The following are preferred technical solutions of this application, but are not intended to limit the technical solutions provided in this application. Through the following preferred technical solutions, the objectives and beneficial effects of this application can be better achieved and realized.
[0032] In some embodiments of the present application, the compound of formula I is selected from the group consisting of the following compounds:
[0033] as well as
[0034] Among them, R A1 and R A2 With the same limitations as above.
[0035] In some embodiments of the present application, the compound of formula I is selected from the group consisting of the following compounds:
[0036] as well as
[0037] Among them, R A1 and R A2 Each independently represents a straight-chain alkyl group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, a branched-chain alkyl group containing 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms,
[0038] R A12 and R A22 Each independently represents a straight-chain alkoxy group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, a branched-chain alkoxy group containing 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms, or
[0039] In some embodiments of the present application, in order to obtain a larger elastic constant, a lower rotational viscosity, a better contrast and an excellent Flicker flicker value, the compound represented by the general formula I contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula I-1 and the compound represented by the general formula I-3.
[0040] In some embodiments of the present application, in order to obtain a larger elastic constant, a lower rotational viscosity, a better contrast and a better Flicker flicker value, the compound represented by general formula I contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by general formula I-1-1, the compound represented by general formula I-1-4 and the compound represented by general formula I-1-5.
[0041] In some embodiments of the present application, it is preferred to adjust the content of the compound of general formula I so that the liquid crystal composition containing it has a larger elastic constant, lower rotational viscosity, better contrast and better Flicker flicker value while maintaining appropriate optical anisotropy, a higher absolute value of dielectric anisotropy and an appropriate clearing point.
[0042] In some embodiments of the present application, the weight percentage of the compound represented by the general formula I in the liquid crystal composition is 0.1%-60% (including any numerical value or sub-range between this range), for example, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 25%, 27%, 30%, 32%, 35%, 37%, 40%, 42%, 45%, 47%, 50%, 55%, 60%, or the range between any two values therein, further preferably 1%-30%, and even more preferably 1%-20%.
[0043] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula I-1 and the compound represented by the general formula I-3 is 1%-30% (including any numerical value or sub-range between the ranges), for example, 1%, 2%, 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%, or a range between any two of the numerical values.
[0044] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula I-1-1, the compound represented by the general formula I-1-4 and the compound represented by the general formula I-1-5 is 1%-20% (including any numerical value or sub-range between this range), for example, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, or a range between any two of the numerical values.
[0045] In some embodiments of the present application, the G represents -O- or -S-.
[0046] In some embodiments of the present application, X1 and X2 represent -F.
[0047] In some embodiments of the present application, the compound represented by formula II is selected from the group consisting of the following compounds:
[0048] as well as
[0049] Wherein, said R3, R4, Z1 and Z3 have the same defined ranges as above;
[0050] Y1 and Y2 each independently represent -O- or -CH2-.
[0051] In some embodiments of the present application, the compound represented by the general formula II is selected from the group consisting of compounds of the general formula II-1 or compounds of the general formula II-2.
[0052] In some embodiments of the present application, R3 represents a straight-chain alkoxy group containing 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, or a straight-chain alkenyloxy group containing 2-6 (e.g., 2, 3, 4, 5, or 6) carbon atoms.
[0053] In some embodiments of the present application, said R4 represents a straight chain alkoxy containing 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, a straight chain alkenyloxy containing 2-6 (e.g., 2, 3, 4, 5 or 6) carbon atoms,
[0054] In some embodiments of the present application, said R4 represents a straight chain alkoxy containing 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, a straight chain alkenyloxy containing 2-6 (e.g., 2, 3, 4, 5 or 6) carbon atoms,
[0055] In some embodiments of the present application, Z1 represents a single bond, -O- or -CH2O-.
[0056] In some embodiments of the present application, Z3 represents a single bond, -O- or -OCH2CH2-.
[0057] In some embodiments of the present application, the compound represented by formula II is selected from the group consisting of the following compounds:
[0058] as well as
[0059] wherein R3 and R4 each independently represent a straight-chain alkoxy group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, or a straight-chain alkenyloxy group containing 2 to 6 (e.g., 2, 3, 4, 5, or 6) carbon atoms;
[0060] ring express
[0061] In some embodiments of the present application, the liquid crystal composition comprises at least two (eg, two, three, four, or five, etc.) compounds represented by the general formula II.
[0062] In some embodiments of the present application, in order to obtain a larger elastic constant, lower rotational viscosity, better contrast and excellent Flicker flicker value, the compound represented by general formula II contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by general formula II-1 and the compound represented by general formula II-2.
[0063] In some embodiments of the present application, in order to obtain a larger elastic constant, lower rotational viscosity, better contrast and excellent Flicker flicker value, the compound of general formula II contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by general formula II-1A, the compound represented by general formula II-1C, the compound represented by general formula II-2A, the compound represented by general formula II-2B and the compound represented by general formula II-2C.
[0064] In some embodiments of the present application, the weight percentage of the compound represented by formula II in the liquid crystal composition is 0.1%-45% (including any numerical value or sub-range between this range), for example, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 25%, 27%, 30%, 32%, 35%, 37%, 40%, 42%, 45%, or the range between any two values therein, further preferably 1%-35%, and even more preferably 1%-30%.
[0065] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula II-1 and the compound represented by the general formula II-2 is 1%-35% (including any numerical value or sub-range between the ranges), for example, 1%, 2%, 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%, or a range between any two of the numerical values.
[0066] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula II-1A, the compound represented by the general formula II-1C, the compound represented by the general formula II-2A, the compound represented by the general formula II-2B and the compound represented by the general formula II-2C is 1%-25% (including any numerical value or sub-range between the range), for example, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, or a range between any two of the numerical values.
[0067] In some embodiments of the present application, the liquid crystal composition further comprises at least one compound represented by the general formula M:
[0068] Among them, R M1 and R M2 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, One or at least two non-adjacent -CH2- groups in the linear 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-;
[0069] ring ring and Ring Each independently expresses described One or at least two -CH2- in the ring may be replaced by -O-, and one or at most two single bonds in the ring may be replaced by double bonds. At most one -H in may be replaced by halogen;
[0070] Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CF2CF2-, -CF2O-, -CH2CH2- or -(CH2)4-;
[0071] n M represents 0, 1, 2, or 3, where n M =2 or 3, the ring Same or different, Z M2 Same or different, when nM When it indicates 0, the ring and Ring Not for
[0072] In some embodiments of the present application, the compound represented by the general formula M is selected from the group consisting of the following compounds:
[0073] Among them, the R M1 and R M2 With the same limitations as above.
[0074] In some embodiments of the present application, the R M1 and R M2 Each independently represents a straight-chain alkyl group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, a straight-chain alkoxy group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, or a straight-chain alkenyl group containing 2 to 8 (e.g., 2, 3, 4, 5, 6, 7 or 8) carbon atoms.
[0075] In some embodiments of the present application, the R M1 and R M2 Each independently represents a straight-chain alkyl group containing 1 to 5 (e.g., 1, 2, 3, 4, or 5) carbon atoms or a straight-chain alkenyl group containing 2 to 5 (e.g., 2, 3, 4, or 5) carbon atoms.
[0076] In some embodiments of the present application, the compound represented by the general formula M is selected from the group consisting of the following compounds:
[0077] Among them, R M1 and R M2 each independently represents a straight-chain alkyl group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, or a branched-chain alkyl group containing 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms;
[0078] R M11 and R M21 each independently represents a straight-chain alkenyl group containing 2 to 8 (e.g., 2, 3, 4, 5, 6, 7, or 8) carbon atoms, or a branched-chain alkenyl group containing 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms;
[0079] R M22represents a straight-chain alkoxy group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms, or a branched-chain alkoxy group containing 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms.
[0080] In some embodiments of the present application, in order to obtain a larger elastic constant, a lower rotational viscosity, a better contrast and an excellent Flicker flicker value, the compound represented by the general formula M contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula M-1, the compound represented by the general formula M-10 and the compound represented by the general formula M-18.
[0081] In some embodiments of the present application, in order to obtain a larger elastic constant, a lower rotational viscosity, a better contrast and an excellent Flicker flicker value, the compound represented by the general formula M contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula M-1-3, the compound represented by the general formula M-10-2, the compound represented by the general formula M-18-1 and the compound represented by the general formula M-18-3.
[0082] In some embodiments of the present application, it is preferred to adjust the content of the compound represented by the general formula M so that the liquid crystal composition containing it has a larger elastic constant, a lower rotational viscosity, a better contrast and a better Flicker flicker value while maintaining appropriate optical anisotropy, a higher absolute value of dielectric anisotropy and an appropriate clearing point.
[0083] In some embodiments of the present application, the weight percentage of the compound represented by the general formula M in the liquid crystal composition is 0.1%-60% (including any numerical value or sub-range between this range), for example, 0.1%, 1%, 3%, 5%, 7%, 9%, 10%, 11%, 13%, 15%, 17%, 19%, 20%, 21%, 23%, 25%, 27%, 29%, 30%, 31%, 33%, 35%, 37%, 39%, 40%, 41%, 43%, 45%, 47%, 49%, 50%, 51%, 53%, 55%, 57%, 59%, 60%, or a range between any two of the numerical values, further preferably 1%-50%, and even more preferably 1%-45%.
[0084] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula M-1, the compound represented by the general formula M-10 and the compound represented by the general formula M-18 is 1%-50% (including any numerical value or sub-range between this range), for example, 1%, 2%, 3%, 5%, 7%, 9%, 10%, 11%, 13%, 15%, 17%, 19%, 20%, 21%, 23%, 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%, or a range between any two of the numerical values.
[0085] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula M-1-3, the compound represented by the general formula M-10-2, the compound represented by the general formula M-18-1 and the compound represented by the general formula M-18-3 is 1%-45% (including any numerical value or sub-range between this range), for example, 1%, 2%, 3%, 5%, 7%, 9%, 10%, 11%, 13%, 15%, 17%, 19%, 20%, 21%, 23%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, or a range between any two of the numerical values.
[0086] In some embodiments of the present application, the liquid crystal composition further comprises at least one compound represented by the general formula N:
[0087] Among them, R E1 and R E2 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, One or at least two non-adjacent -CH2- groups in the linear 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-;
[0088] ring and Ring Each independently expresses wherein One or at least two -CH2- in the ring may be replaced by -O-, and one or at most two single bonds in the ring may be replaced by double bonds, wherein the One or at least two -H groups in the ring may be independently replaced by -F, -Cl, or -CN, and -CH= in one or more rings may be replaced by -N=;
[0089] Z E1 and Z E2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-;
[0090] L E1 and L E2 Each independently represents -H, halogen, an alkyl group containing 1 to 3 (e.g., 1, 2, or 3) carbon atoms, or an alkoxy group containing 1 to 3 (e.g., 1, 2, or 3) carbon atoms; and
[0091] n E1 Indicates 0, 1, 2, or 3, n E2 Represents 0 or 1, and 0≤n E1 +n E2 ≤3; when n E1 When it means 2 or 3, the ring Same or different, Z E1 Same or different.
[0092] In some embodiments of the present application, the L E1 and L E2 All represent -H.
[0093] In some embodiments of the present application, the R E1 and R E2 each independently represents a straight-chain alkyl group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, a straight-chain alkoxy group containing 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms, a straight-chain alkenyl group containing 2 to 8 (e.g., 2, 3, 4, 5, 6, 7 or 8) carbon atoms,
[0094] In some embodiments of the present application, the Z E1 and Z E2 Each independently represents a single bond, -CO-O-, -CH2O-, -OCH2-, -CH=CH-, -CH2CH2- or -(CH2)4-.
[0095] In some embodiments of the present application, the compound represented by the general formula N is selected from the group consisting of the following compounds:
[0096] as well as
[0097] Among them, the R E1 and R E2 With the same limitations as above.
[0098] In some embodiments of the present application, in order to obtain a larger elastic constant, lower rotational viscosity, better contrast and excellent Flicker flicker value, the compound represented by general formula N contains at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by general formula N-8, the compound represented by general formula N-9, the compound represented by general formula N-13, the compound represented by general formula N-20, the compound represented by general formula N-25 and the compound represented by general formula N-27.
[0099] In some embodiments of the present application, it is preferred to adjust the content of the compound represented by the general formula N so that the liquid crystal composition containing it has a larger elastic constant, lower rotational viscosity, better contrast and better Flicker flicker value while maintaining appropriate optical anisotropy, a higher absolute value of dielectric anisotropy and an appropriate clearing point.
[0100] In some embodiments of the present application, the weight percentage of the compound represented by the general formula N in the liquid crystal composition is 0.1%-60% (including any numerical value or sub-range between this range), for example, 0.1%, 1%, 3%, 5%, 7%, 9%, 10%, 11%, 13%, 15%, 17%, 19%, 20%, 21%, 23%, 25%, 27%, 29%, 30%, 31%, 33%, 35%, 37%, 39%, 40%, 41%, 43%, 45%, 47%, 49%, 50%, 51%, 53%, 55%, 57%, 59%, 60%, or a range between any two of the numerical values, further preferably 1%-50%, and even more preferably 15%-50%.
[0101] In some embodiments of the present application, the weight percentage of the liquid crystal composition comprising at least one (for example, two, three, four or five, etc.) compound selected from the group consisting of the compound represented by the general formula N-8, the compound represented by the general formula N-9, the compound represented by the general formula N-13, the compound represented by the general formula N-20, the compound represented by the general formula N-25 and the compound represented by the general formula N-27 is 1% to 50% (including any numerical value or sub-range between the ranges), for example, 1%, 2%, 3%. , 5%, 7%, 9%, 10%, 11%, 13%, 15%, 17%, 19%, 20%, 21%, 23%, 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%, or a range between any two of the values.
[0102] In addition to the above compounds, the liquid crystal composition of the present application may also include any one or a combination of at least two of common nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, polymerizable monomers, and additives.
[0103] In some embodiments of the present application, the liquid crystal composition further includes at least one additive.
[0104] In a preferred embodiment, the additive includes any one or a combination of at least two of a dopant, an antioxidant, an ultraviolet absorber, an infrared absorber or a light stabilizer.
[0105] In some embodiments of the present application, the dopant is selected from any one or a combination of at least two of the following compounds:
[0106] Wherein, * represents the chiral site.
[0107] In some embodiments of the present application, the weight percentage of the dopant in the liquid crystal composition is 0%-5%, for example, it can be 0%, 0.01%, 0.05%, 0.1%, 0.2%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5% or 5%, etc., and more preferably 0.01%-1%.
[0108] In some embodiments of the present application, the antioxidant, light stabilizer, ultraviolet absorber and other additives are preferably the following compounds:
[0109] Wherein, n represents a positive integer of 1-12, for example, 1, 2, 4, 6, 8, 9, 10, 11 or 12; n2 represents a positive integer of 1-18; and “+” represents a free radical.
[0110] In some embodiments of the present application, the antioxidant is selected from any one or a combination of at least two of the following compounds:
[0111] In some embodiments of the present application, in the liquid crystal composition, the weight percentage of the light stabilizer is 0%-5%, for example, it can be 0%, 0.01%, 0.05%, 0.1%, 0.2%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5% or 5%, etc., and more preferably 0.01%-1%.
[0112] In a second aspect, the present application provides a liquid crystal display device, comprising the liquid crystal composition as described in the first aspect.
[0113] Compared with the related art, this application has the following beneficial effects:
[0114] In the present application, by designing the specific composition and structure of the compound in the liquid crystal composition, and further by using at least one compound of the general formula I containing a cyclohexene structure and at least one compound of the general formula II containing a dibenzopentacyclic structure in combination, the resulting liquid crystal composition has appropriate optical anisotropy, a high absolute value of dielectric anisotropy, an appropriate clearing point, a large elastic constant, a low rotational viscosity, a good contrast ratio, and a good Flicker value, effectively improving the response speed, helping to enhance the display effect of the liquid crystal material, and can be applied to high-contrast, fast-response IPS liquid crystal display mode.
[0115] Still other aspects will become apparent upon reading and understanding the detailed description. DETAILED DESCRIPTION
[0116] To facilitate understanding of the present application, the present application lists the following examples. Those skilled in the art should understand that the examples are only provided to help understand the present application and should not be considered as specific limitations of the present application.
[0117] For ease of expression, in the following examples, the group structures of the liquid crystal compositions are represented by the codes listed in Table 1:
[0118] Table 1
[0119] In Table 1, the short straight lines represent the insertion sites of the groups.
[0120] Take the following compound as an example:
[0121] If the structural formula is represented by the codes listed in Table 1, it can be expressed as: nCCGF, where n in the code represents the number of carbon atoms in the left-hand alkyl group. For example, if n is "3", it means that the alkyl group is -C3H7; C in the code represents cyclohexyl, G represents 2-fluoro-1,4-phenylene, and F represents fluorine.
[0122] In the following examples and comparative examples, the abbreviated codes for the performance test items are shown in Table 2:
[0123] Table 2 Abbreviated codes for performance test items
[0124] in:
[0125] Cp: obtained by melting point test.
[0126] Δn: Δn=n e -n0 was measured using an Abbe refractometer under a sodium lamp (589 nm) at 25°C.
[0127] 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: 25°C, 1 kHz, VA-type test cell with a cell thickness of 6 μm.
[0128] Flicker value: Tested using a DMS505 tester in Flicker mode, and the logarithm of the test value is obtained. Test conditions: 25°C, 60 Hz, V22 voltage drive, and a negative FFS test cell with a cell thickness of 3μm.
[0129] K ave : where K 11 , K 22 and K 33 It is calculated by testing the CV curve of the liquid crystal using an LCR meter and a VA test box; the test conditions are: 6μm VA test box, V = 0.1 ~ 20V.
[0130] γ1: Measured using the LCM-2 liquid crystal property evaluation system; test conditions: 25°C, 160-240V, test box thickness 20μm.
[0131] CR: Use DMS 505 tester to test the transmittance of the liquid crystal cell at 255 grayscale voltage and 0 grayscale voltage, that is, T r255 and T r0 , by Tr255 / T r0 get.
[0132] The compounds used in the following examples can be synthesized by known methods or obtained through commercial channels. These synthesis techniques are conventional, and the resulting liquid crystal compositions have been tested to meet the standards of electronic compounds.
[0133] Liquid crystal compositions were prepared according to the ratios of the liquid crystal compositions in the following examples. The preparation of the liquid crystal compositions was carried out according to conventional methods in the art, such as mixing in a prescribed ratio by heating, ultrasonication, suspension, etc.
[0134] Comparative Example 1
[0135] This comparative example provides a liquid crystal composition, which includes the components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0136] Comparative Example 2
[0137] This comparative example provides a liquid crystal composition, which includes the components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0138] Example 1
[0139] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0140] Example 2
[0141] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0142] Example 3
[0143] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0144] Example 4
[0145] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0146] Example 5
[0147] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0148] Example 6
[0149] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0150] Example 7
[0151] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0152] Example 8
[0153] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0154] Example 9
[0155] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0156] Example 10
[0157] This embodiment provides a liquid crystal composition, which includes components in the weight percentages shown in the following table, and is filled between two substrates of a liquid crystal display for performance testing:
[0158] As can be seen from the above content, the present application designs the specific composition and structure of the compound in the liquid crystal composition, and further uses at least one compound of the general formula I containing a cyclohexene structure and at least one compound of the general formula II containing a dibenzopentacyclic structure in combination, so that the obtained liquid crystal composition has a large average elastic constant (14.8 to 16.7), a low rotational viscosity (90 to 127), a good contrast ratio (1760 to 2500) and a good Flicker value (-64.45 to -58.32) while maintaining an appropriate optical anisotropy (0.098 to 0.11), a high absolute value of dielectric anisotropy (3.4 to 5.2) and an appropriate clearing point (80.1 to 107°C), while improving the response rate, which helps to improve the display effect of the liquid crystal material and is applied to the high-contrast and fast-response IPS liquid crystal display mode.
[0159] The applicant declares that while the above-mentioned embodiments are used to illustrate the detailed process flow of the present application, the present application is not limited to the above-mentioned detailed process flow, which does not mean that the present application must rely on the above-mentioned detailed process flow in order to be implemented. Those skilled in the art should understand that any improvements to the present application, equivalent replacements for the raw materials of the present application's products, addition of auxiliary ingredients, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present application.
Claims
1. A liquid crystal composition comprising at least one compound represented by General Formula I and at least one compound represented by General Formula II: and Among them, R A1 and R A2 each independently represents a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms, One or at least two non-adjacent -CH2- groups in the straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms may each independently be -O-, -CO-, -CO-O-, -O-CO-, or Substitution; Ring Sum ring Each independently represents wherein, at least one loop or loop For R3 and R4 each independently represent -H, halogen, a straight-chain or branched alkyl group having 1 to 12 carbon atoms, The straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms, One or at least two non-adjacent -CH2- in may each independently be replaced by -CH=CH-, -C≡C-, -O-, -S-, -CO-, -CO-O- or -O-CO-, and one or at least two -H in the foregoing groups may each independently be replaced by -F or -Cl; Z1 and Z2 each independently represent a single bond, -O-, -S-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-; Z3 represents a single bond, -O(CH2) a - or -S(CH2) a -; a represents an integer from 0 to 3; Ring Sum ring Each independently represents The said One or at least two of the -CH2- therein may be replaced by -O-, and one or at most two single bonds in non-adjacent rings may be replaced by double bonds; the One or at least two -H in may each independently be replaced by -F, -Cl, -CN, -CH3 or -OCH3, and one or at least two -CH= in the rings may be replaced by -N=; G represents -O-, -S-, -CF2-, -NH-, -NF- or -CO-; X1 and X2 each independently represent -H, a halogen, a halogenated or unhalogenated alkyl group having 1 to 3 carbon atoms, or a halogenated or unhalogenated alkoxy group having 1 to 3 carbon atoms; n1 and n2 each independently represent 0, 1 or 2; when n1 = 2, the ring identical or different, Z1 is identical or different; when n2 = 2, the ring Same or different, Z2 is the same or different.
2. The liquid crystal composition according to claim 1, wherein, The compounds of general formula I are selected from the group consisting of the following compounds: and Among them, R A1 and R A2 have the same defined scope as R A1 and R A2 described in claim 1.
3. The liquid crystal composition according to claim 1, wherein The weight percentage of the compound represented by the general formula I in the liquid crystal composition is 0.1% - 60%.
4. The liquid crystal composition according to claim 1, wherein The compound represented by the general formula II is selected from the group consisting of the following compounds: and Wherein, R3, R4, Z1 and Z3 have the same defined ranges as R3, R4, Z1 and Z3 described in claim 1; Y1 and Y2 each independently represent -O- or -CH2-.
5. The liquid crystal composition according to claim 1, wherein, The weight percentage of the compound represented by the general formula II in the liquid crystal composition is 0.1% - 45%.
6. The liquid crystal composition according to claim 1, wherein The liquid crystal composition further comprises at least one compound represented by General Formula M: wherein, R M1 and R M2 each independently represents a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms, One or at least two non-adjacent -CH2- in the straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; Ring Ring Sum ring Each independently represents The said One or at least two of the -CH2- therein may be replaced by -O-, and one or at most two single bonds in the ring may be replaced by double bonds. The At most one -H in may be replaced by a halogen; Z M1 and Z M2 each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CF2CF2-, -CF2O-, -CH2CH2- or -(CH2)4-; n M represents 0, 1, 2, or 3, where when n M = 2 or 3, the ring identical or different, Z M2 identical or different, when n M represents 0, the ring Sum ring not being 7. The liquid crystal composition according to claim 6, wherein, The compound represented by the general formula M is selected from the group consisting of the following compounds: and Among them, R M1 and R M2 have the same defined scope as R M1 and R M2 described in claim 6.
8. The liquid crystal composition according to claim 1, wherein The liquid crystal composition further comprises at least one compound represented by General Formula N: wherein, R E1 and R E2 each independently represents a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms, One or at least two non-adjacent -CH2- in the straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-; Ring Sum ring Each independently represents wherein the One or at least two of the -CH2- therein may be replaced by -O-, and one or at most two single bonds in the ring may be replaced by double bonds, wherein the One or at least two -H in may each independently be replaced by -F, -Cl, or -CN, and one or at least two -CH= in the rings may be replaced by -N=; Z E1 and Z E2 each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH═CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-; L E1 and L E2 each independently represents -H, a halogen, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms; and, n E1 represents 0, 1, 2, or 3, and n E2 represents 0 or 1, and 0 ≤ n E1 + n E2 ≤ 3; when n E1 represents 2 or 3, the ring Same or different, Z E1 Same or different.
9. The liquid crystal composition according to claim 8, wherein, The compound represented by the general formula N is selected from the group consisting of the following compounds: and Among them, the R E1 and R E2 have the same defined scope as the R E1 and R E2 described in claim 8.
10. A liquid crystal display device, which comprises the liquid crystal composition according to any one of claims 1 - 9.
Citation Information
Patent Citations
Liquid crystal composition with negative dielectric anisotropy, and liquid crystal display element using liquid crystal composition
CN104471027A
Compound, liquid crystal composition, liquid crystal display element and liquid crystal display
CN112079687A
Liquid crystal medium
CN113881444A
Liquid crystal medium
CN117004406A
Liquid crystal medium
CN117285938A
Cited By
Liquid crystal composition and liquid crystal display device
US12662630B2