Liquid crystal composition and liquid crystal display device

JP7912684B2Active Publication Date: 2026-08-28JIANGSU HECHENG DISPLAY TECH CO LTD
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Patent Information

Application Number
JP2025531126
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2022-12-09
Filing Date
2023-11-07
Publication Date
2026-08-28
Estimated Expiration
2043-11-07

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Benefits of technology

【0066】 従来技術に比べて、本発明は、以下の有益な効果を有する。

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Abstract

The present invention provides a liquid crystal composition and a liquid crystal display device. The liquid crystal composition includes at least one compound of general formula I and at least one compound of general formula II. The present invention provides a liquid crystal composition that has a K ave value is large, and ε ⊥ Since it has high conductivity, small light scattering, and suitable optical anisotropy and clearing point, a liquid crystal display device containing it has good transmittance and contrast, and is suitable for VA, IPS or FFS type display devices.
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Description

[Technical Field]

[0001] This invention belongs to the technical field of liquid crystal displays, and more specifically, relates to liquid crystal compositions and liquid crystal display devices. [Background technology]

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

[0003] The optical anisotropy of a liquid crystal composition is related to the contrast of the element. Depending on the element's display mode, either high or low optical anisotropy (i.e., appropriate optical anisotropy) is required. The product (Δn × d) of the composition's optical anisotropy (Δn) and the element's cell thickness (d) is designed to maximize the contrast. The appropriate value of this product depends on the type of operating mode, but for elements with small cell thicknesses, a liquid crystal composition with high optical anisotropy is preferable.

[0004] Contrast is the ratio of the brightest to the darkest area. A higher ratio results in a greater range of tonal gradations from black to white, and richer color reproduction. Contrast has a very important impact on visual effects. Generally, higher contrast makes images sharper, more striking, and colors more vivid and beautiful, while lower contrast makes the entire image appear blurry. High contrast contributes significantly to image sharpness, detail, and tonal gradation. Higher contrast results in better image effects and more saturated colors, while lower contrast makes the image appear blurry and colors less vivid.

[0005] Liquid crystal display elements containing liquid crystal compositions with a large absolute value of dielectric anisotropy can reduce the base voltage, reduce the driving voltage, and further reduce power consumption.

[0006] Liquid crystal display elements containing liquid crystal compositions with a low threshold voltage can effectively reduce display power consumption and, in particular, provide longer battery life in consumables (e.g., portable electronic products such as mobile phones and tablet computers). However, liquid crystal compositions with a low threshold voltage (generally containing large dielectric polar groups) have a low degree of order in their liquid crystal molecules, and the K22C (K22C) reflects the degree of order in the liquid crystal molecules. ave As the value also decreases, it affects light leakage and contrast in the liquid crystal material, and achieving both at the same time is usually difficult.

[0007] A person skilled in the art has found that, based on conventional measurements of the light leakage performance of IPS-LCDs, the main causes of the light leakage problem in liquid crystal display devices are liquid crystal (LC) scattering, rubbing uniformity, light leakage from color filter films (CF / TFT scattering) and polarize ability, and light scattering accounts for 63% of the factors affecting light leakage performance.

[0008] the following relational expression

Formula

[0009] In addition, the relational expression between contrast (CR) and luminance (L) is: CR=L 255 / L0×100%, where L 255 is the on-state luminance, and L0 is the off-state luminance. It can be seen that changes in L0 have a significant impact on CR. In the off-state, L0 is not related to the dielectric constant characteristics of liquid crystal molecules, but is related to the LC scattering of the liquid crystal material itself. The smaller the LC scattering is, the smaller L0 becomes, so CR is significantly improved.

[0010]

Formula

[0011] In order to overcome the shortcomings of the prior art, the object of the present invention is to provide a liquid crystal composition and a liquid crystal display device. In the present invention, by designing the components of the liquid crystal composition, the manufactured liquid crystal composition is K ave The value is large, ε ⊥ It has high optical properties, low light scattering, and appropriate optical anisotropy and transparency point, making it suitable for VA, IPS, or FFS type display elements. [Means for solving the problem]

[0012] To achieve this objective, the present invention employs the following technical approach.

[0013] In a first aspect, the present invention provides a liquid crystal composition comprising at least one compound of general formula I and at least one compound of general formula II, [ka] In the formula, R1 is a halogenated or non-halogenated linear alkyl group containing 1 to 12 (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms, or a halogenated or non-halogenated branched alkyl group containing 3 to 12 (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms. [ka] Representing any one of the above, one or at least two non-adjacent -CH2- groups in the halogenated or non-halogenated linear alkyl group containing 1 to 12 carbon atoms, or the halogenated or non-halogenated branched alkyl group containing 3 to 12 carbon atoms, may each be independently substituted with a -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO- group. R 11 teeth, [ka] X1 represents -O- or -S-, n 11 This represents 0, 1, 2, 3, or 4. [ka] teeth, [ka] This represents, R2 and R3 are each independently a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), and a branched alkyl group containing 3 to 12 carbon atoms (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12). [ka] Representing any one of the above, one or at least two non-adjacent -CH2- groups in the linear alkyl group containing 1 to 12 carbon atoms or the branched alkyl group containing 3 to 12 carbon atoms may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO- groups. [ka] teeth, [ka] Represents the above [ka] One or at least two of the -CH2- may be independently substituted with -O-, and one or at least two single bonds in the ring may be independently substituted with double bonds, [ka] One or at least two of the -H atoms may be independently substituted with -F, -Cl, -CN, -CH3, or -OCH3, and one or at least two of the -CH= atoms in the ring may be independently substituted with -N=. L1 to L4 each independently represent a halogen atom. X2 represents -O- or -S-, and X3 represents -O- or -CH2-. Z1 represents a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O-, or -OCF2-. n1 represents 0, 1, or 2, and if n1 represents 2, [ka] Z1 may be the same or different, and n2 represents either 1 or 2.

[0014] In this invention, by designing the components of the liquid crystal composition, the manufactured liquid crystal composition is K ave The value is large, ε ⊥ It has high optical properties, low light scattering, and appropriate optical anisotropy and transparency point, making it suitable for VA, IPS, or FFS type display elements.

[0015] The halogen atom is a fluorine atom, chlorine This includes atoms, bromine atoms, and iodine atoms (the same applies hereinafter).

[0016] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The objectives and beneficial effects of the present invention can be better achieved and realized by the following preferred technical solutions.

[0017] In some embodiments of the present invention, the compound of general formula I is [ka] [ka] It is a combination of one or at least two compounds having the following structure: In the formula, the above [ka] X1, X2, L1, L2, Z1 and n 11 It has the same scope of protection as described above.

[0018] In some embodiments of the present invention, the above [ka] teeth, [ka] It represents.

[0019] In some embodiments of the present invention, L1 and L2 both represent a fluorine atom.

[0020] In some embodiments of the present invention, the compound of general formula I is the compound of general formula I-1 or the compound of general formula I-9.

[0021] In some embodiments of the present invention, the liquid crystal composition comprises at least two compounds having the general formula I-1 and / or the general formula I-9.

[0022] In some embodiments of the present invention, the weight percentage of the compound of general formula I in the liquid crystal composition is 0.1% to 35%, and may be, for example, 0.1%, 0.2%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 25%, 26%, 28%, 30%, 32%, or 35%, and more preferably 2% to 25%.

[0023] In some embodiments of the present invention, preferably by adjusting the content of the compound of general formula I, the liquid crystal composition containing it has appropriate optical anisotropy, appropriate transparency point, and high ε ⊥ , large K ave It has a small value and exhibits low light scattering.

[0024] In some embodiments of the present invention, the compound of general formula II is [ka] That Having a structure It is a combination of one or at least two of the compounds.

[0025] In some embodiments of the present invention, L3 and L4 both represent fluorine atoms.

[0026] In some embodiments of the present invention, the compound of general formula II includes the compound of general formula II-2 and / or the compound of general formula II-4.

[0027] In some embodiments of the present invention, the liquid crystal composition comprises at least two (for example, two, three, four, or five) compounds of general formula II.

[0028] In some embodiments of the present invention, the compound of general formula II comprises at least one compound selected from the group consisting of the compounds of general formula II-1 and general formula II-3, and at least one compound selected from the group consisting of the compounds of general formula II-2 and general formula II-4.

[0029] In some embodiments of the present invention, the weight percentage of the compound of general formula II in the liquid crystal composition is 0.1% to 60%, and may be, for example, 0.1%, 0.2%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, or 60%, and more preferably 8% to 60%.

[0030] In some embodiments of the present invention, preferably by adjusting the content of the compound of general formula II, the liquid crystal composition containing it has appropriate optical anisotropy, appropriate transparency point, and high ε ⊥ , large K ave The value is adjusted to have low light scattering.

[0031] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of general formula N, [ka] In the formula, R N1 and R N2 Each of these independently comprises a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), a branched alkyl group containing 3 to 12 carbon atoms, [ka] The linear alkyl group containing 1 to 12 carbon atoms and the branched alkyl group containing 3 to 12 carbon atoms may each be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-. [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two of the -CH2- groups may be substituted with -O- groups, and one or at least two of the single bonds in the ring may be substituted with double bonds. [ka] One or at least two of the -H atoms may be independently substituted with -F, -Cl, or -CN, and one or at least two of the -CH= atoms in the ring may be substituted with -N=. Z N1 and Z N2 These independently represent a single bond, -CO-O-, -O-CO-, -CH=CH-, -C≡C-, -CF2CF2-, -(CH2)4-, -CF2O-, or -OCF2-. L N1 and L N2 Each independently represents -H, an alkyl group or halogen atom containing 1 to 3 (for example, 1, 2, or 3) carbon atoms, and n N1 n represents 0, 1, 2, or 3, N2 represents 0 or 1, and 0 ≤ n N1 +n N2 ≤ 3, n N1 If it represents 2 or 3, [ka] They may be the same or different, Z N1 They may be the same or different.

[0032] In some embodiments of the present invention, the compound of general formula N is [ka] [ka] [ka] It is one or at least two combinations of compounds having the following structure.

[0033] In some embodiments of the present invention, the compound of general formula N is selected from the group consisting of compounds of general formula N-2, general formula N-3, general formula N-7, general formula N-10, general formula N-13, general formula N-15, and general formula N-17.

[0034] In some embodiments of the present invention, the weight percentage of the compound of general formula N in the liquid crystal composition is 0.1% to 50%, and may be, for example, 0.1%, 0.2%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or 50%, and more preferably 2% to 45%.

[0035] In some embodiments of the present invention, preferably by adjusting the content of the compound of general formula N, the liquid crystal composition containing it exhibits appropriate optical anisotropy, appropriate transparency point, and high ε ⊥ , large K ave It has a small value and exhibits low light scattering.

[0036] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of general formula M, [ka] In the formula, R M1 and R M2 Each of these independently comprises a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), and a branched alkyl group containing 3 to 12 carbon atoms (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12). [ka] The linear alkyl group containing 1 to 12 carbon atoms or the branched alkyl group containing 3 to 12 carbon atoms may have one or at least two non-adjacent -CH2- groups independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-. [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two of the -CH2- groups may be substituted with -O- groups, and one or at least two of the single bonds in the ring may be substituted with double bonds. [ka] Many of the -H atoms may be substituted with halogen atoms. Z M1 and Z M2 These each independently represent 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, and n M If represents 2, [ka] They may be the same or different, Z M2 They may be the same or different.

[0037] In some embodiments of the present invention, the compound of general formula M is [ka] [ka] [ka] It is one or at least two combinations of compounds having the following structure.

[0038] In some embodiments of the present invention, the compound of general formula M is selected from the group consisting of compounds of general formula M-1, general formula M-2, general formula M-4, general formula M-11, general formula M-13, general formula M-21, general formula M-23, general formula M-24, and general formula M-27.

[0039] In some embodiments of the present invention, the weight percentage of the compound of general formula M in the liquid crystal composition is 0.1% to 60%, and may be, for example, 0.1%, 0.2%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, or 60%, and more preferably 30% to 50%.

[0040] In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of general formula B, [ka] In the formula, R B1 and R B2 Each of these independently comprises a halogen atom, -CF3, -OCF3, a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 8, 9, 10, 11 or 12), and a branched alkyl group containing 3 to 12 carbon atoms (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12). [ka] Represents a linear alkyl group containing 1 to 12 carbon atoms, a branched alkyl group containing 3 to 12 carbon atoms, [ka] One or at least two non-adjacent -CH2- groups may each be independently substituted with -O-, -CO-, -CO-O-, -O-CO-, a linear alkyl group containing 1 to 12 carbon atoms, a branched alkyl group containing 3 to 12 carbon atoms, [ka] One or at least two non-adjacent -CH2- can each be independently substituted with -CH=CH- or -C≡C-. [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two non-adjacent -CH2- groups may be substituted with -O- groups, and one or at least two single bonds in the ring may be substituted with double bonds. [ka] One or at least two of the -H atoms may be independently substituted with -CN, -F, or -Cl, and one or at least two of the -CH= atoms in the ring may be substituted with -N=. X B represents -O-, -S-, or -CO-, L B1 and L B2 These each independently represent -H, -F, -Cl, -CF3, or -OCF3. Z B1 and Z B2 These independently represent a single bond, -O-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O-, or -OCF2-. n B1 and n B2 Each of these independently represents 0, 1, or 2, and n B1 If represents 2, [ka] n can be the same or different, B2 If represents 2, [ka] They may be the same or different, Z B2 They may be the same or different.

[0041] In some embodiments of the present invention, the compound of general formula B is [ka] It is one or at least two combinations of compounds having the following structures: In the formula, R B1 ' represents a halogen atom, -CF3, -OCF3, a linear alkyl group containing 1 to 8 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, or 8), a branched alkyl group containing 3 to 8 carbon atoms (for example, 3, 4, 5, 6, 7, or 8), an alkoxy group containing 1 to 8 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, or 8), and an alkenyl group containing 2 to 8 carbon atoms (for example, 2, 3, 4, 5, 6, 7, or 8). X B1 This represents -O- or -CH2-, R B2 , X B and Z B1 It has the same scope of protection as described above.

[0042] 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% to 20%, and may be, for example, 0.1%, 0.2%, 0.5%, 1%, 2%, 4%, 5%, 7%, 8%, 10%, 12%, 14%, 16%, 18%, or 20%.

[0043] In some embodiments of the present invention, to apply the liquid crystal composition of the present invention to a highly transmissive liquid crystal display, the liquid crystal composition further comprises at least one compound of general formula A-1 and / or at least one compound of general formula A-2, [ka] In the formula, R A1 and R A2 Each of these independently comprises a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), and a branched alkyl group containing 3 to 12 carbon atoms (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12). [ka] This represents a linear alkyl group containing 1 to 12 carbon atoms or a branched alkyl group containing 3 to 12 carbon atoms. [ka] One or at least two non-adjacent -CH2- groups may each be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-, and the linear alkyl group containing 1 to 12 carbon atoms, the branched alkyl group containing 3 to 12 carbon atoms, [ka] One or at least two of the -H atoms may be independently substituted with -F or -Cl. [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two of the -CH2- groups may be substituted with -O- groups, and one or at least two of the single bonds in the ring may be substituted with double bonds. [ka] One or at least two of the -H atoms may be independently substituted with -F, -Cl, or -CN, and one or at least two of the -CH= atoms in the ring may be substituted with -N=. Z A11 , Z A21 and Z A22 These independently represent a single bond, -CH2CH2-, -CF2CF2-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -CF=CF-, -CH2O-, or -OCH2-. L A11 , L A12 , L A13 , L A21 and L A22 Each of these independently represents -H, an alkyl group or halogen atom containing 1 to 3 (for example, 1, 2, or 3) carbon atoms, X A1 and X A2 Each of these independently represents a halogen atom, a linear halogenated alkyl group having 1 to 5 carbon atoms (for example, 1, 2, 3, 4, or 5), a branched halogenated alkyl group having 3 to 5 carbon atoms (for example, 3, 4, or 5), a halogenated alkoxy group having 1 to 5 carbon atoms (for example, 1, 2, 3, 4, or 5), a halogenated alkenyl group having 2 to 5 carbon atoms (for example, 2, 3, 4, or 5), or a halogenated alkenyloxy group having 2 to 5 carbon atoms (for example, 2, 3, 4, or 5). nA11 n represents 0, 1, 2, or 3, A11 If it represents 2 or 3, [ka] They may be the same or different, Z A11 They may be the same or different. n A12 This represents 1 or 2, and n A12 If represents 2, [ka] They may be the same or different, and n A2 n represents 0, 1, 2, or 3, A2 If it represents 2 or 3, [ka] They may be the same or different, Z A21 They may be the same or different.

[0044] In some embodiments of the present invention, the compound of general formula A-1 is [ka] [ka] [ka] It is one or at least two combinations of compounds having the following structure: In the formula, R A1 This includes a linear alkyl group containing 1 to 8 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, or 8), and a branched alkyl group containing 3 to 8 carbon atoms (for example, 3, 4, 5, 6, 7, or 8). [ka] represents, in said straight-chain alkyl group containing 1 to 8 carbon atoms and branched-chain alkyl group containing 3 to 8 carbon atoms, one or at least two non-adjacent -CH2- groups may each be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and in said straight-chain alkyl group containing 1 to 8 carbon atoms and branched-chain alkyl group containing 3 to 8 carbon atoms,

Chemical Formula

[0045] In some embodiments of the present invention, in said liquid crystal composition, the weight percentage of the compound of general formula A-1 is 0.1% to 50%, for example, may be 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% or 50%.

[0046] In some embodiments of the present invention, the compound of general formula A-2 is

Chemical Formula

Chem.

[0047] In some embodiments of the present invention, in the liquid crystal composition, the weight percentage of the compound of general formula A-2 is 0.1% to 50%, and may be, 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 the like.

[0048] In some embodiments of the present invention, the sum of the weight percentages of the compound of general formula A-1 and the compound of general formula A-2 in the liquid crystal composition is 0.1% to 60%, and may be, 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%, or 60%.

[0049] In some embodiments of the present invention, the liquid crystal composition further comprises at least one polymerizable compound of general formula RM, [ka] In the formula, R P1 This includes -H, a halogen atom, -CN, -Sp2-P2, a linear alkyl group containing 1 to 12 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), and a branched alkyl group containing 3 to 12 carbon atoms (for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12). [ka] Represents a linear alkyl group containing 1 to 12 carbon atoms, a branched alkyl group containing 3 to 12 carbon atoms, [ka] One or at least two non-adjacent -CH2- atoms may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-, and one or at least two -H atoms may be independently substituted with -F or -Cl. [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two non-adjacent -CH2- groups may be substituted with -O- groups, and one or at least two single bonds in the ring may be substituted with double bonds. [ka] One or at least two of the -H groups are independently -F, -Cl, -CN, -Sp3-P3, a halogenated or non-halogenated linear alkyl group containing 1 to 12 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), or a halogenated or non-halogenated linear alkoxy group containing 1 to 11 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11). [ka] It may be substituted with, and one or at least two -CH= in the ring may each be independently substituted with -N=, [ka] Each of them operates independently. [ka] This represents, [ka] One or at least two of the -H groups are independently -F, -Cl, -CN, -Sp3-P3, a halogenated or non-halogenated linear alkyl group containing 1 to 12 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), or a halogenated or non-halogenated linear alkoxy group containing 1 to 11 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11). [ka] It may be substituted with, and one or at least two -CH= in the ring may each be independently substituted with -N=, where X0 represents -O-, -S-, -CO-, -CF2-, -NH- or -NF-, P1, P2, and P3 each independently represent polymerizable groups. Sp1, Sp2, and Sp3 each independently represent a spacer group or a single bond. Z C1 and Z C2 These are, independently, -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 represents a single bond, R 1 and R 2 Each independently represents a linear alkyl group containing 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms, and a branched alkyl group containing 3 to 12 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12) carbon atoms, and d represents an integer from 1 to 4 (e.g., 1, 2, 3, or 4), and If a represents 0, 1, or 2, and b represents 0 or 1, and a represents 2, [ka] They may be the same or different, Z C1 They may be the same or different.

[0050] The polymerizable groups according to the present invention are groups applied to polymerization reactions (e.g., radical or ionic polymerization, addition polymerization, or condensation polymerization), or groups applied to addition or condensation in the main chain of a polymer. For chain polymerization, polymerizable groups containing -CH=CH- or -C≡C- are particularly preferred, and for ring-opening polymerization, for example, oxetanyl groups or epoxy groups are particularly preferred.

[0051] In some embodiments of the present invention, the polymerizable groups P1, P2, and P3 are each independently [ka] Or it represents -SH, preferably, [ka] Or -SH, more preferably, [ka] That is the case.

[0052] 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).

[0053] As used herein, the term “spacer group” refers to a flexible group that bonds a mesogenic group to a polymerizable group in a polymerizable compound. Typical spacer groups include, for example, -(CH2)p1-, -(CH2CH2O)q1-CH2CH2-, -(CH2CH2S)q1-CH2CH2-, -(CH2CH2NH)q1-CH2CH2-, and -CR 0 R 00 -(CH2)p1- or -(SiR 0 R 00 -O)p1- where p1 represents an integer from 1 to 12, q1 represents an integer from 1 to 3, R 0 and R 00Each of these independently represents -H, a linear or branched alkyl group containing 1 to 12 carbon atoms, or a cyclic alkyl group containing 3 to 12 carbon atoms. In the present invention, the spacer group is preferably -(CH2)p1-, -(CH2)p1-O-, -(CH2)p1-O-CO-, -(CH2)p1-CO-O-, -(CH2)p1-O-CO-O-, or -CR 0 R 00 It is -(CH2)p1-.

[0054] In some embodiments of the present invention, the compound of general formula RM is [ka] [ka] [ka] [ka] It is one or at least two combinations of compounds having the following structure: In the formula, X1~X 10 and X 12 Each of these independently comprises -F, -Cl, -Sp3-P3, a linear alkyl group containing 1 to 5 carbon atoms (for example, 1, 2, 3, 4, or 5), and an alkoxy group containing 1 to 5 carbon atoms (for example, 1, 2, 3, 4, or 5). [ka] It represents.

[0055] In some embodiments of the present invention, the weight percentage of the polymerizable compound of general formula RM in the liquid crystal composition is 0.001% to 5%, 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%, or 5%.

[0056] In some embodiments of the present invention, the liquid crystal composition further comprises at least one additive.

[0057] The aforementioned additives include nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, dopants, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers, or light stabilizers.

[0058] In some embodiments of the present invention, the dopant is [ka] [ka] It contains one or at least two combinations of the following compounds.

[0059] In some embodiments of the present invention, the weight percentage of the dopant in the liquid crystal composition is 0% to 5%, and may be, for example, 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%, and more preferably 0.01% to 1%.

[0060] In some embodiments of the present invention, the additives such as antioxidants, light stabilizers, and ultraviolet absorbers are preferably, [ka] [ka] [ka] It is a compound that In the formula, n represents a positive integer between 1 and 12, such as 1, 2, 4, 6, 8, 9, 10, 11, or 12.

[0061] In some embodiments of the present invention, the antioxidant is [ka] It is one or at least two combinations selected from the following compounds.

[0062] In some embodiments of the present invention, the weight percentage of the light stabilizer in the liquid crystal composition is 0% to 5%, and may be, for example, 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%, and more preferably 0.01% to 1%.

[0063] For the sake of ease of calculation, in this invention, the sum of the weight percentages of compounds having different general formulas in the liquid crystal composition is 100%, and the content of additives is not included in the total content of the liquid crystal composition. In other words, when additives are added, the total content of each component in the liquid crystal composition becomes >100%.

[0064] A liquid crystal composition containing the polymerizable compound of the present invention can polymerize even in the absence of a polymerization initiator, but a polymerization initiator may be included to promote polymerization. Examples of polymerization initiators include, but are not limited to, benzoin ethers, benzophenones, acetophenones, benzyl ketals, and acyl phosphine oxides.

[0065] In a second aspect, the present invention provides a liquid crystal display device, the liquid crystal display device comprising the liquid crystal composition described in the first aspect. [Effects of the Invention]

[0066] Compared to the prior art, the present invention has the following beneficial effects.

[0067] In this invention, by designing the components of the liquid crystal composition, the manufactured liquid crystal composition is K ave The value is large, ε ⊥ It has high optical properties, low light scattering, and appropriate optical anisotropy and transparency point, making it suitable for VA, IPS, or FFS type display elements. [Modes for carrying out the invention]

[0068] To facilitate understanding of the present invention, embodiments of the present invention are listed below. Those skilled in the art should understand that these embodiments are merely for the purpose of understanding the present invention and should not be considered as specifically limiting the present invention.

[0069] The origins of some of the components in the examples and comparative examples are as follows:

[0070] To facilitate explanation, in each of the following examples, the base structure of the liquid crystal composition is represented by the code shown in Table 1.

[0071] Table 1 [Table 1]

[0072] In Table 1, the dashed lines represent the connection points of the base.

[0073] Let's take the following compound with the structural formula as an example. [ka] When the structural formula is represented by the codes shown in Table 1, it can be expressed as nCCGF, where n in the code represents the number of carbon atoms in the alkyl group at the left end. For example, when n is "3", it indicates that the alkyl group is -C3H7, C in the code represents cyclohexanyl, G represents 2-fluoro-1,4-phenylene group, and F represents fluorine.

[0074] In the following examples and comparative examples, the abbreviations of performance measurement items are as shown in Table 2.

[0075] Table 2 Abbreviations of performance measurement items

Table 2

Math

[0076] Each component used in the liquid crystal compositions of the following examples can be synthesized by known methods or obtained commercially, and as a result of measurement, each component of the obtained liquid crystal composition conforms to the specifications for electronic compounds.

[0077] The liquid crystal compositions in the following examples are formulated with each component (the formula in parentheses at the end of each component in each example is the general formula to which the component belongs), and mixed using conventional manufacturing methods, such as heating, ultrasound, or suspension, to obtain the liquid crystal composition. Comparative Example 1

[0078] This comparative example provides a liquid crystal composition containing the components shown in the table below in terms of weight percentages, and the performance is measured by filling these components between two substrates of a liquid crystal display.

[0079] [Table 3] Comparative Example 2

[0080] This comparative example provides a liquid crystal composition containing the components shown in the table below in terms of weight percentages, and the performance is measured by filling these components between two substrates of a liquid crystal display.

[0081] [Table 4] [Examples]

[0082] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0083] [Table 5]

[0084] As can be seen from the comparison between Example 1 and Comparative Examples 1 and 2, the liquid crystal composition of the present invention, by suitably selecting the structures of the compound of general formula I and the compound of general formula II, exhibits appropriate optical anisotropy, appropriate transparency point, and a large ε. ⊥ , large K ave It has a low scattering coefficient (ratio reduced by 11% to 9%), and accordingly the contrast is improved by 11% to 9%. [Example]

[0085] This example provides a liquid crystal composition, which comprises components in the weight percentages shown in the following table. The liquid crystal composition is filled between two substrates of a liquid crystal display to perform performance measurement.

[0086] [Table 6] [Example]

[0087] This example provides a liquid crystal composition, which comprises components in the weight percentages shown in the following table. The liquid crystal composition is filled between two substrates of a liquid crystal display to perform performance measurement.

[0088] [Table 7] [Example]

[0089] This example provides a liquid crystal composition, which comprises components in the weight percentages shown in the following table. The liquid crystal composition is filled between two substrates of a liquid crystal display to perform performance measurement.

[0090] [Table 8] [Example]

[0091] This example provides a liquid crystal composition, which comprises components in the weight percentages shown in the following table. The liquid crystal composition is filled between two substrates of a liquid crystal display to perform performance measurement.

[0092] [Table 9] [Example]

[0093] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0094] [Table 10] [Examples]

[0095] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0096] [Table 11] [Examples]

[0097] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0098] [Table 12] [Examples]

[0099] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0100] [Table 13] [Examples]

[0101] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0102] [Table 14] [Examples]

[0103] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0104] [Table 15] [Examples]

[0105] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0106] [Table 16] [Examples]

[0107] This embodiment provides a liquid crystal composition comprising the components shown in the table below in weight percentages, and the composition is filled between two substrates of a liquid crystal display for performance measurement.

[0108] [Table 17]

[0109] As can be seen from the above, in the present invention, by designing the components of the liquid crystal composition, the manufactured liquid crystal composition is K ave The value is large, ε ⊥ Due to its high optical anisotropy and low light scattering (a ratio reduction of 9% to 48%), along with appropriate optical anisotropy and transparency, liquid crystal display devices containing it have good transmittance and contrast and are applicable to VA, IPS, or FFS type display elements.

[0110] The applicant argues that while the present invention describes the liquid crystal composition and liquid crystal display device of the present invention using the above-described examples, the present invention is not limited to the above-described examples, and that this does not mean that the present invention cannot be implemented without relying on the above-described examples. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of each raw material in the product of the present invention, addition of auxiliary components, and selection of specific methods all fall within the scope of protection and disclosure of the present invention. [Industrial applicability]

[0111] The liquid crystal composition according to the present invention can be applied to the field of liquid crystals.

Claims

1. It comprises at least one compound of general formula I and at least one compound of general formula II, 【Chemistry 1】 In the formula, R 1 This includes halogenated or non-halogenated linear alkyl groups containing 1 to 12 carbon atoms, and halogenated or non-halogenated branched alkyl groups containing 3 to 12 carbon atoms. 【Chemistry 2】 Representing any one of the above, one or at least two non-adjacent -CH groups in the halogenated or non-halogenated linear alkyl group containing 1 to 12 carbon atoms, or the halogenated or non-halogenated branched alkyl group containing 3 to 12 carbon atoms. 2 Each of the - groups may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO- groups. R 11 teeth, 【Transformation 3】 This represents X 1 represents -O- or -S-, n 11 represents 0, 1, 2, 3, or 4. 【Chemistry 4】 teeth, 【Transformation 5】 This represents, R 2 and R 3 Each of these independently consists of a linear alkyl group containing 1 to 12 carbon atoms, and a branched alkyl group containing 3 to 12 carbon atoms. 【Transformation 6】 Representing any one of the above, one or at least two non-adjacent -CH groups from the linear alkyl group containing 1 to 12 carbon atoms or the branched alkyl group containing 3 to 12 carbon atoms. 2 Each of the - groups may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO- groups. 【Transformation 7】 teeth, 【Transformation 8】 Represents the above 【Chemistry 9】 one or at least two -CH of 2 - may each independently be substituted with -O-, one or at least two single bonds in the ring may each independently be substituted with a double bond, the 【Chemistry 10】 One or at least two of the -H atoms are, independently, -F, -Cl, -CN, and -CH. 3 , or -OCH 3 It may be substituted with, and one or at least two -CH= in the ring may each be independently substituted with -N=, L 1 ~L 4 Each of these independently represents a halogen atom. X 2 represents -O- or -S-, X 3 is -O- or -CH 2 - represents, Z 1 These are single bonds, -CO-O-, -O-CO-, and -CH 2 O-, -OCH 2 -, -CH=CH-, -C≡C-, -CH 2 CH 2 -, -CF 2 CF 2 -, - (CH 2 ) 4 -, -CF 2 O- or -OCF 2 - represents, n 1 represents 0, 1, or 2, and n 1 If represents 2, 【Chemistry 11】 Z may be the same or different. 1 They may be the same or different, and n 2 A liquid crystal composition characterized in that represents 1 or 2.

2. The compound of general formula I is 【Chemistry 12(1)】 【Chemistry 12(2)】 It is a combination of one or at least two compounds having the following structure: In the formula, the above 【Chemistry 13】 X 1 , X 2 , L 1 , L 2 Z 1 and n 11 The liquid crystal composition according to claim 1, characterized in that it has the same protective range as claim 1.

3. The compound of general formula II mentioned above is 【Chemistry 14】 The liquid crystal composition according to claim 1 or 2, characterized in that it is a combination of one or at least two compounds having the structure described above.

4. The liquid crystal composition further comprises at least one compound of general formula N, 【Chemistry 15】 In the formula, R N1 and R N2 Each of these independently consists of a linear alkyl group containing 1 to 12 carbon atoms, and a branched alkyl group containing 3 to 12 carbon atoms. 【Chemistry 16】 This represents one or two or more non-adjacent -CH groups from the linear alkyl group containing 1 to 12 carbon atoms or the branched alkyl group containing 3 to 12 carbon atoms. 2 Each of the hyphens may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-. 【Chemistry 17】 Each of them operates independently. 【Chemistry 18】 This represents, 【Chemistry 19】 One or at least two of the -CH 2 The - may be substituted with -O-, and one or at least two single bonds in the ring may be substituted with double bonds. 【Chemistry 20】 One or at least two of the -H atoms may be independently substituted with -F, -Cl, or -CN, and one or at least two of the -CH= atoms in the ring may be substituted with -N=. Z N1 and Z N2 These are, independently, single bonds, -CO-O-, -O-CO-, -CH=CH-, -C≡C-, and -CF 2 CF 2 -, - (CH 2 ) 4 -, -CF 2 O- or -OCF 2 - represents, L N1 and L N2 Each of these independently represents -H, an alkyl group containing 1 to 3 carbon atoms, or a halogen atom, and n N1 represents 0, 1, 2, or 3, and n N2 represents 0 or 1, and 0 ≤ n N1 +n N2 ≤ 3, n N1 If it represents 2 or 3, 【Chemistry 21】 Z may be the same or different. N1 The liquid crystal composition according to claim 1, characterized in that the elements may be the same or different.

5. The compound of general formula N is 【Chemistry 22(1)】 【Chemistry 22(2)】 【Chemistry 22(3)】 The liquid crystal composition according to claim 4, characterized in that it is one or at least two combinations of compounds having the structure described above.

6. The liquid crystal composition further comprises at least one compound of general formula M, 【Chemistry 23】 In the formula, R M1 and R M2 Each of these independently consists of a linear alkyl group containing 1 to 12 carbon atoms, and a branched alkyl group containing 3 to 12 carbon atoms. 【Chemistry 24】 Represents one or at least two non-adjacent -CH groups in the linear alkyl group containing 1 to 12 carbon atoms or the branched alkyl group containing 3 to 12 carbon atoms. 2 Each of the hyphens may be independently substituted with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, or -O-CO-. 【Chemistry 25】 Each of them operates independently. 【Chemistry 26】 This represents, 【Chemistry 27】 One or at least two of the -CH 2 The - may be substituted with -O-, and one or at least two single bonds in the ring may be substituted with double bonds. 【Chemistry 28】 Many of the -H atoms may be substituted with halogen atoms. Z M1 and Z M2 These are, independently, single bonds, -CO-O-, -O-CO-, and -CH 2 O-, -OCH 2 -, -C≡C-, -CH=CH-, -CH 2 CH 2 - or - (CH 2 ) 4 - represents, and n M represents 0, 1, or 2, and n M If represents 2, 【Chemistry 29】 Z may be the same or different. M2 The liquid crystal composition according to claim 1, characterized in that the elements may be the same or different.

7. The compound of general formula M is 【Chemistry 30(1)】 【Chemistry 30(2)】 [Chemical 30(3)] The liquid crystal composition according to claim 6, characterized in that it is one or at least two combinations of compounds having the structure described above.

8. The liquid crystal composition according to claim 2, characterized in that the liquid crystal composition comprises at least two compounds having the general formula I-1 and / or compounds having the general formula I-9.

9. The liquid crystal composition according to claim 3, wherein the compound of general formula II comprises at least one compound selected from the group consisting of the compounds of general formula II-1 and general formula II-3, and at least one compound selected from the group consisting of the compounds of general formula II-2 and general formula II-4.

10. A liquid crystal display device characterized by comprising the liquid crystal composition described in claim 1.

11. The above 【Chemistry 31】 teeth, 【Chemistry 32】 This represents, In the above, L1 and L2 both represent fluorine atoms. The compound of general formula I is the compound of general formula I-1 or the compound of general formula I-9. The liquid crystal composition according to claim 2, wherein the weight percentage of the compound of general formula I is 0.1% to 35%.

12. The liquid crystal composition according to claim 11, wherein the weight percentage of the compound of general formula I is 2% to 25%.

13. Both L3 and L4 represent fluorine atoms, The compound of general formula II includes the compound of general formula II-2 and / or the compound of general formula II-4. The liquid crystal composition comprises at least two compounds of the general formula II, The liquid crystal composition according to claim 3, characterized in that the weight percentage of the compound of general formula II is 0.1% to 60%.

14. The liquid crystal composition according to claim 13, wherein the weight percentage of the compound of general formula II is 8% to 60%.

15. The compound of general formula N is 【Transformation 33】 It is one or at least two combinations of compounds having the following structure: The liquid crystal composition according to claim 5, characterized in that the weight percentage of the compound of general formula N is 0.1% to 50%.

16. The liquid crystal composition according to claim 15, wherein the weight percentage of the compound of general formula N is 2% to 45%.

17. The compound of general formula M is 【Transformation 34】 It is one or at least two combinations of compounds having the following structure: The liquid crystal composition according to claim 7, characterized in that the weight percentage of the compound of general formula M is 0.1% to 60%.

18. The liquid crystal composition according to claim 17, wherein the weight percentage of the compound of general formula M is 30% to 50%.

Citation Information

Patent Citations

  • Liquid crystal composition with negative dielectric constant and application thereof

    CN110396411A

  • Compound having dibenzofuran ring, liquid crystal composition, and liquid crystal display element

    WO2018155340A1

  • Compounds having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element

    WO2019107394A1