Liquid Crystal Composition and Liquid Crystal Display Device Using the Same
A liquid crystal composition with enhanced dielectric and elastic properties addresses the limitations of existing devices, improving contrast, transmittance, and response speed in liquid crystal displays.
Patent Information
- Application Number
- JP2021143030
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-09-17
- Filing Date
- 2021-09-02
- Publication Date
- 2025-07-08
- Estimated Expiration
- 2041-09-02
AI Technical Summary
Existing liquid crystal display devices face challenges in achieving high contrast, transmittance, and short response times due to limitations in dielectric anisotropy and elastic constants, leading to issues like light leakage and limited driving voltage adjustment.
A liquid crystal composition comprising specific compounds of general formulas I, II, and III, which enhance the vertical dielectric constant, elastic constants, and transmittance while maintaining appropriate optical anisotropy and dielectric anisotropy, is developed.
The composition achieves a larger vertical dielectric constant, higher transmittance, and shorter response times, resulting in improved contrast, faster response speed, and better temperature stability in liquid crystal display devices.
Smart Images

Figure 0007704617000001 
Figure 0007704617000002 
Figure 0007704617000003
Abstract
Description
Technical Field
[0001] The present invention relates to the field of liquid crystals, and more specifically, to liquid crystal compositions and liquid crystal display devices including the liquid crystal compositions.
Background Art
[0002] Liquid crystal display elements can be used in various household electrical appliances such as watches and calculators, measuring instruments, automotive panels, word processors, computers, printers, televisions, etc. Depending on the type of display mode, liquid crystal display elements can be 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), VA (vertical alignment), etc. Depending on the driving method of the element, liquid crystal display elements can be classified into PM (passive matrix) type and AM (active matrix) type. PM can be classified into types such as static and multiplex. AM can be classified into types such as TFT (thin film transistor) and MIM (metal insulator metal). The types of TFT include amorphous silicon and polycrystalline silicon. The latter can be classified into high-temperature type and low-temperature type according to the manufacturing process. Depending on the type of light source, liquid crystal display elements can be classified into reflective type using natural light, transmissive type using backlight, and transflective type using both natural light and backlight.
[0003] The liquid crystal display element contains a liquid crystal composition having a nematic phase, and the composition has appropriate characteristics. By improving the characteristics of the composition, an AM element with good characteristics can be obtained. The correlation between the characteristics of the composition and the characteristics of the AM element is summarized in Table 1 below.
[0004]
Table 1
[0005] In the application of liquid crystal display devices, the influence of contrast on the visual effect is very important. Generally, the higher the contrast, the clearer and more prominent the image, and the brighter and more beautiful the colors. On the contrary, when the contrast is low, the whole screen looks blurry. High contrast makes a significant contribution to the sharpness, detail display, and grayscale display of images. High-contrast products have advantages in terms of black-and-white contrast, sharpness, integrity, etc. Contrast also has a great impact on the video display effect. Since the conversion between light and dark in dynamic images is fast, the higher the contrast, the easier it is for the human eye to distinguish such a conversion process.
[0006] Transmittance formula T of IPS mode r ∝|Δε| / ε ⊥ (Here, T r represents the transmittance, "∝" represents the "inversely proportional" relationship, Δε represents the dielectric anisotropy, and ε ⊥ represents the dielectric constant in the direction perpendicular to the molecular axis). Based on this, in order to improve the transmittance of the liquid crystal medium, it is possible to try to reduce Δε of the liquid crystal medium, but generally the adjustment range of the driving voltage of the same product is limited. Also, since the liquid crystal molecules tilt in the Z-axis direction under the action of the vertical component of the fringe electric field, their optical anisotropy changes, and the formula T r =sin 2 (2χ)sin 2(Based on (πΔnd / λ) (where χ is the angle between the optical axis of the liquid crystal layer and the optical axis of the polarizer, Δn is the optical anisotropy, d is the cell gap of the liquid crystal cell, and λ is the wavelength), it can be seen that the effective Δn*d affects T, and in order to improve the transmittance of the liquid crystal medium, it is conceivable to increase Δn*d, but the design of the retardation amount of each product is constant.)
[0007] On the other hand, based on the test of the light leakage performance of the conventional IPS-LCD, those skilled in the art have found that the factors causing the light leakage problem of the liquid crystal display device are light scattering (LC scattering), rubbing uniformity, light leakage of the color filter film (CF / TFT scattering), and polarization ability, and the proportion of light scattering in the influencing factors of the light leakage performance is 63%.
[0008] The relational expression is
Number
[0009] Also, the relational expression between the contrast (CR) and the luminance (L) is as follows. CR = L 255 / L0×100% Here, L 255is the on-state luminance, and L0 is the off-state luminance. As can be seen from the above, it should be the change in L0 that significantly affects CR. In the off state, L0 is independent of the dielectric properties of the liquid crystal molecules and is related to the LC Scattering of the liquid crystal material itself. The smaller the LC Scattering, the smaller L0 becomes, and CR is significantly improved thereby.
[0010] In view of the above situation, a general method for improving contrast and transmittance is: (1) While keeping the dielectric anisotropy Δη of the liquid crystal composition constant, by improving ε ⊥ a method that can effectively improve the transmittance, and (2) from two aspects, a method of improving the transmittance by increasing the value of the average elastic constant K ave of the liquid crystal composition to make the order degree of the liquid crystal molecules higher and reduce the light leakage.
[0011] From the perspective of the manufacture of liquid crystal materials, the various properties of liquid crystal materials restrict and affect each other, and the improvement of a certain property index may change other properties. Therefore, in order to manufacture a liquid crystal material with appropriate properties in all aspects, generally creative efforts are required.
Summary of the Invention
Problems to be Solved by the Invention
[0012] An object of the present invention is to provide a liquid crystal composition having a larger vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance while maintaining an appropriate clearing point, an appropriate optical anisotropy, and an appropriate absolute value of the dielectric anisotropy.
[0013] Another object of the present invention is to provide a liquid crystal display device including the above liquid crystal composition.
Means for Solving the Problems
[0014] To achieve the above object of the invention, the present invention provides a liquid crystal composition, and the liquid crystal composition is at least one compound of general formula I, and [Chemical formula] I at least one compound selected from the group consisting of a compound of general formula II, a compound of general formula III, and combinations thereof, [Chemical formula] II [Chemical formula] III comprising, wherein R2, R3, R5 and R6 are each independently a linear or branched alkyl group containing 1 to 12 carbon atoms, [Chemical formula] , [Chemical formula] or [Chemical formula] representing, wherein one or two or more non-adjacent -CH2- of the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, R1 and R4 each independently represent a linear or branched alkenyl group containing 2 to 12 carbon atoms, or a linear or branched alkenyloxy group containing 2 to 11 carbon atoms, ring [Chemical formula] and ring [Chemical formula] are each independently [Chemical formula] or [Chem.] represents, where [Chem.] one or more of the -CH2- may be replaced by -O-, and one or more of the single bonds in the ring may be replaced by double bonds, [Chem.] one or more of the -H may each independently be replaced by -F, -Cl, or -CN, and one or more of the -CH= in the ring may be replaced by -N=, Z1 and Z2 each independently represent a single bond, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C-, -CH2CH2-, -CF2CF2-, -(CH2)4-, -CF2O- or -OCF2-, L1, L2, L3 and L4 each independently represent -F, -Cl, -CF3, -OCF3 or -CHF2, n1 represents 0, 1, 2 or 3, n2 represents 0 or 1, and 0 < n1 + n2 ≤ 3, and when n1 = 2 or 3, the ring [Chem.] may be the same or different, Z1 may be the same or different, and the ring [Chem.] and the ring [Chem.] at least one of the rings is [Chem.] , [Chemistry] or [Chemistry] represents.
[0015] In some embodiments of the present invention, both L1 and L2 are -F.
[0016] In some embodiments of the present invention, preferably, R2 represents a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms, and more preferably, R2 represents a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms.
[0017] In some embodiments of the present invention, the compound of general formula I is [Chemistry] I-1, and [Chemistry] I-2, and [Chemistry] I-3, and [Chemistry] I-4, and is selected from the group consisting of the compounds of wherein a represents an integer from 0 to 4, and b represents an integer from 1 to 4.
[0018] In some embodiments of the present invention, preferably, by adjusting the content of the compound of general formula I, when the absolute value of the dielectric anisotropy of the liquid crystal composition containing the same is at the same or approximate level, a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance can be obtained.
[0019] 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 50%, for example, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, and preferably, the weight percentage of the compound of general formula I in the liquid crystal composition is 0.5% to 40%.
[0020] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is at the same or approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance, the liquid crystal composition preferably contains at least two (for example, two or three) compounds of general formula I.
[0021] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is at the same or approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance, the liquid crystal composition preferably contains at least one (for example, one, two, or three) compound of general formula I-2, and particularly preferably contains at least one compound of general formula I-2 in which a represents 0.
[0022] In some embodiments of the present invention, the weight percentage of the compound selected from the group consisting of the compound of general formula II, the compound of general formula III, and combinations thereof in the liquid crystal composition is 0.1% to 50%, for example, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%.
[0023] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is at the same or approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance, the liquid crystal composition preferably contains at least one compound of general formula I and at least one compound of general formula II.
[0024] In some embodiments of the present invention, preferably, R3 represents a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms. More preferably, R3 represents a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms.
[0025] In some embodiments of the present invention, preferably, R4 represents a linear or branched alkenyl group containing 2 to 8 carbon atoms, or a linear or branched alkenyloxy group containing 2 to 7 carbon atoms. More preferably, R4 represents a linear or branched alkenyl group containing 2 to 5 carbon atoms, or a linear or branched alkenyloxy group containing 2 to 4 carbon atoms.
[0026] In some embodiments of the present invention, R4 is preferably selected from groups represented by any of formula (V1) to formula (V9), and particularly preferably, is formula (V1), formula (V2), formula (V7) or formula (V8). The groups represented by formula (V1) to formula (V9) are, as shown below,
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0027] In some embodiments of the present invention, R4 is preferably selected from groups represented by any of formula (OV1) to formula (OV9), and particularly preferably, is formula (OV1), formula (OV2), formula (OV8) or formula (OV9). The groups represented by formula (OV1) to formula (OV9) are, as shown below,
Chemical formula
[0028] In some embodiments of the present invention, preferably, by adjusting the content of the compound of general formula II, when the absolute value of the dielectric anisotropy of the liquid crystal composition containing the same is at the same or approximate level, a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance can be obtained.
[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% to 35%, for example, 0%, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, and preferably, the weight percentage of the compound of general formula II in the liquid crystal composition is 0.5% to 30%.
[0030] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is at the same or approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance, the liquid crystal composition preferably contains at least one compound of general formula I and at least one compound of general formula III.
[0031] In some embodiments of the present invention, both L3 and L4 are -F.
[0032] In some embodiments of the present invention, the compound of general formula III is [Chemical formula] III-1, and [Chemical formula] III-2, and [Chemical formula] III-3, and [Chemical formula] III-4, and [Chemical formula] III-5, and [Chemical formula] III-6, and [Chemical formula] III-7 and [Chemical formula] III-8 and [Chemical formula] III-9 and [Chemical formula] III-10 and [Chemical formula] III-11 and [Chemical formula] III-12 and [Chemical formula] III-13 and [Chemical formula] III-14 and [Chemical formula] III-15 and [Chemical formula] III-16 and [Chemical formula] III-17 and [Chemical formula] III-18 and [Chemical formula] III-19 and [Chemical formula] III-20 and
Chemical formula
[0033] In some embodiments of the present invention, the compound of general formula III is selected from the group consisting of the compound of general formula III-1, the compound of general formula III-2, the compound of general formula III-3, the compound of general formula III-6, the compound of general formula III-8, the compound of general formula III-9, the compound of general formula III-10, the compound of general formula III-11, the compound of general formula III-12, the compound of general formula III-13, the compound of general formula III-14, the compound of general formula III-15, the compound of general formula III-20, the compound of general formula III-21 and combinations thereof.
[0034] In some embodiments of the present invention, the compound of general formula III is selected from the group consisting of the compound of general formula III-4, the compound of general formula III-5, the compound of general formula III-6, the compound of general formula III-7, the compound of general formula III-16, the compound of general formula III-17, the compound of general formula III-18, the compound of general formula III-19 and combinations thereof.
[0035] In some embodiments of the present invention, when n1 + n2 = 1, the rings are connected by a non-single bond.
[0036] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is the same or at an approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time and a high transmittance, the liquid crystal composition preferably contains at least two compounds of general formula III.
[0037] In some embodiments of the present invention, preferably, by adjusting the content of the compound of general formula III, when the absolute value of the dielectric anisotropy of the liquid crystal composition containing the same is at the same or approximate level, a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance can be obtained.
[0038] In some embodiments of the present invention, the weight percentage of the compound of general formula III in the liquid crystal composition is 0% to 50%, for example, 0%, 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 45%, 46%, 48%, 50%, and preferably, the weight percentage of the compound of general formula III in the liquid crystal composition is 0.5% to 40%, and more preferably, the weight percentage of the compound of general formula III in the liquid crystal composition is 0.5% to 30%.
[0039] In some embodiments of the present invention, in order to maintain a short response time and a high transmittance, preferably, the lower limit value and the upper limit value of the content of the compound of general formula III are high.
[0040] In some embodiments of the present invention, when the absolute value of the dielectric anisotropy is at the same or approximate level, in order to obtain a large vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance, the liquid crystal composition preferably contains at least one compound of general formula I, at least one compound of general formula II, and at least one compound of general formula III.
[0041] In some embodiments of the present invention, the liquid crystal composition of the present invention further contains at least one compound of general formula M,
Chemical formula
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chemical formula
[0042] In some embodiments of the present invention, the compound of general formula M is
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
[0043] In some embodiments of the present invention, the weight percentage of the compound of general formula M in the liquid crystal composition is 1% to 80%, for example, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 70%, 72%, 74%, 76%, 78%, 80%, and preferably, the weight percentage of the compound of general formula M in the liquid crystal composition is 15% to 60%.
[0044] In some embodiments of the present invention, the content of the compound of general formula M needs to be appropriately adjusted according to necessary characteristics such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burning-in, dielectric anisotropy, etc.
[0045] Regarding the content of the compound of general formula M, when it is necessary to maintain that the viscosity of the liquid crystal composition of the present invention is low and the response time is short, preferably, its lower limit value is high and its upper limit value is high. Furthermore, when it is necessary to maintain that the clearing point of the liquid crystal composition of the present invention is high and the temperature stability is good, preferably, its lower limit value is high and its upper limit value is high. In order to maintain a low driving voltage and increase the absolute value of the dielectric anisotropy, preferably, its lower limit value is lowered and its upper limit value is lowered.
[0046] In some embodiments of the present invention, R M1 and R M2 are preferably, each independently, a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms, and R M1 and R M2is more preferably, each independently, a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms, where R M1 and R M2 are even more preferably, each independently, a linear or branched alkyl group containing 1 to 5 carbon atoms, a linear or branched alkoxy group containing 1 to 4 carbon atoms, or a linear or branched alkenyl group containing 2 to 5 carbon atoms.
[0047] In some embodiments of the present invention, R M1 and R M2 are preferably, each independently, a linear alkenyl group containing 2 to 8 carbon atoms, and even more preferably, each independently, a linear alkenyl group containing 2 to 5 carbon atoms.
[0048] In some embodiments of the present invention, preferably, either one of R M1 and R M2 is a linear alkenyl group containing 2 to 5 carbon atoms, and the other is a linear alkyl group containing 1 to 5 carbon atoms.
[0049] In some embodiments of the present invention, R M1 and R M2 are preferably, each independently, a linear alkyl group containing 1 to 8 carbon atoms, or a linear alkoxy group containing 1 to 7 carbon atoms, and even more preferably, each independently, a linear alkyl group containing 1 to 5 carbon atoms, or a linear alkoxy group containing 1 to 4 carbon atoms.
[0050] In some embodiments of the present invention, preferably, either one of R M1 and R M2 is a linear alkyl group containing 1 to 5 carbon atoms, and the other is a linear alkyl group containing 1 to 5 carbon atoms, or a linear alkoxy group containing 1 to 4 carbon atoms, and even more preferably, RM1 and R M2 Both are each independently a linear alkyl group containing 1 to 5 carbon atoms.
[0051] In some embodiments of the present invention, when reliability is emphasized, preferably, R M1 and R M2 are both alkyl groups. When reducing the volatility of the compound is emphasized, preferably, R M1 and R M2 are both alkoxy groups. When reducing the viscosity is emphasized, preferably, at least one of R M1 and R M2 is an alkenyl group.
[0052] In some embodiments of the present invention, the liquid crystal composition of the present invention further contains at least one compound of general formula N,
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0053] In some embodiments of the present invention, the compound of general formula N is
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0054] 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 60%, for example, 0.1%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, and preferably, the weight percentage of the compound of general formula N in the liquid crystal composition is 1% to 55%.
[0055] In some embodiments of the present invention, the compound of general formula N is selected from the group consisting of the compound of general formula N-2, the compound of general formula N-5, and combinations thereof.
[0056] In some embodiments of the present invention, the compound of general formula N is selected from the group consisting of the compound of general formula N-10, the compound of general formula N-12, the compound of general formula N-17, the compound of general formula N-31, and combinations thereof.
[0057] In some embodiments of the present invention, when it is necessary to maintain a low viscosity and a short response time of the liquid crystal composition of the present invention, preferably, the lower limit value and the upper limit value of the content of the compound of general formula N are low. Further, when it is necessary to maintain a high clearing point and good temperature stability of the liquid crystal composition of the present invention, preferably, the lower limit value and the upper limit value of the content of the compound of general formula N are low. Also, in order to maintain a low driving voltage and increase the absolute value of the dielectric anisotropy, preferably, the lower limit value and the upper limit value of the content of the compound of general formula N are increased.
[0058] In some embodiments of the present invention, preferably, R N1 and R N2 each independently represent a linear or branched alkyl group containing 1 to 10 carbon atoms, a linear or branched alkoxy group containing 1 to 9 carbon atoms, or a linear or branched alkenyl group containing 2 to 10 carbon atoms. More preferably, R N1 and R N2 each independently represent a linear or branched alkyl group containing 1 to 8 carbon atoms, a linear or branched alkoxy group containing 1 to 7 carbon atoms, or a linear or branched alkenyl group containing 2 to 8 carbon atoms. Even more preferably, R N1 and R N2 each independently represent a linear or branched alkyl group containing 1 to 5 carbon atoms, a linear or branched alkoxy group containing 1 to 4 carbon atoms, or a linear or branched alkenyl group containing 2 to 5 carbon atoms.
[0059] In some embodiments of the present invention, the liquid crystal composition of the present invention further comprises at least one compound of general formula A-1 and / or a compound of general formula A-2,
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0060] In some embodiments of the present invention, the compound of general formula A-1 is [Chemical formula] A-1-1, [Chemical formula] A-1-2, [Chemical formula] A-1-3, [Chemical formula] A-1-4, [Chemical formula] A-1-5, [Chemical formula] A-1-6, [Chemical formula] A-1-7, [Chemical formula] A-1-8, [Chemical formula] A-1-9, [Chemical formula] A-1-10, [Chemical formula] A-1-11, [Chemical formula] A-1-12, [Chemical formula] A-1-13, and [Chemical formula] A-1-14, and [Chemical formula] A-1-15, and [Chemical formula] A-1-16, and [Chemical formula] A-1-17, and [Chemical formula] A-1-18, and selected from the group consisting of compounds of wherein R A1 represents a straight-chain or branched alkyl group containing 1 to 8 carbon atoms, and one or two or more non-adjacent -CH2- groups among the straight-chain or branched alkyl groups containing 1 to 8 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, and one or more -H present in these groups may each independently be replaced by -F or -Cl, R v and R w each independently represents -CH2- or -O-, L A11 L A12 L A11 L A12 L A14 L A15 and L A16 each independently represents -H or -F, L A13 and L A13 each independently represents -H or -CH3, X A1 represents -F, -CF3 or -OCF3, and v and w each independently represent 0 or 1.
[0061] In some embodiments of the present invention, the weight percentage of the compound of general formula A-1 in the liquid crystal composition is 0% to 50%, for example, 0%, 0.1%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%.
[0062] Regarding the preferred content of the compound of general formula A-1, when the viscosity of the liquid crystal composition of the present invention is maintained low and the response speed is fast, preferably, the lower limit value is slightly lowered and the upper limit value is slightly lowered. Further, when the clearing point of the liquid crystal composition of the present invention is maintained high and the temperature stability is good, preferably, the lower limit value is slightly lowered and the upper limit value is slightly lowered. Also, when trying to maintain a low driving voltage and increase the absolute value of the dielectric anisotropy, preferably, the lower limit value is slightly increased and the upper limit value is slightly increased.
[0063] In some embodiments of the present invention, the compound of general formula A-2 is
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0064] In some embodiments of the present invention, the weight percentage of the compound of general formula A-2 in the liquid crystal composition is 0% to 50%, for example, 0%, 0.1%, 1%, 2%, 4%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%.
[0065] Regarding the preferred content of the compound of general formula A-2, when maintaining the viscosity of the liquid crystal composition of the present invention low and having a fast response speed, preferably the lower limit value is slightly lowered and the upper limit value is slightly lowered. Further, when maintaining the clearing point of the liquid crystal composition of the present invention high and having good temperature stability, preferably the lower limit value is slightly lowered and the upper limit value is slightly lowered. Also, when trying to maintain a low driving voltage and increase the absolute value of the dielectric anisotropy, preferably the lower limit value is slightly increased and the upper limit value is slightly increased.
[0066] In addition to the above compounds, the liquid crystal composition of the present invention may contain general nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, dopants, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers, or light stabilizers, etc.
[0067] Dopants that may preferably be added to the liquid crystal composition according to the present invention are, as shown below,
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chem.
Chem.
[0068] In some embodiments of the present invention, the weight percentage occupied by the dopant in the liquid crystal composition is 0% to 5%, preferably, the weight percentage occupied by the dopant in the liquid crystal composition is 0.01% to 1%.
[0069] Also, additives such as antioxidants and light stabilizers used in the liquid crystal composition of the present invention are preferably the following substances.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
[0070] Preferably, the light stabilizer is selected from the light stabilizers shown below. [Chemical formula] [Chemical formula] [Chemical formula]
[0071] In some embodiments of the present invention, the total weight percentage of the light stabilizer in the liquid crystal composition is 0% to 5%, preferably, the total weight percentage of the light stabilizer in the liquid crystal composition is 0.01% to 1%, and more preferably, the total weight percentage of the light stabilizer in the liquid crystal composition is 0.01% to 0.1%.
[0072] On the other hand, the present invention further provides a liquid crystal display device, and the liquid crystal display device includes the above liquid crystal composition.
[0073] In some embodiments of the present invention, the above liquid crystal composition is particularly applicable to VA, IPS or FFS type display elements. [Advantages of the Invention]
[0074] Compared with the prior art, the liquid crystal composition of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an appropriate absolute value of dielectric anisotropy, and further has a larger vertical dielectric constant, a large ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a large K value, a short response time, and a high transmittance. As a result, the liquid crystal display device including the same maintains an appropriate usable temperature range and an appropriate threshold voltage, and further has better contrast, a fast response speed, and good transmittance.
Embodiments for Carrying Out the Invention
[0075] Hereinafter, the present invention will be described in conjunction with specific embodiments. It should be noted that the following examples are illustrative of the present invention and are only for explaining the present invention, and do not limit the present invention. Without departing from the spirit or scope of the present invention, other combinations and various improvements within the concept of the present invention can be made.
[0076] For ease of explanation, in the following examples, the functional group structures of each compound are represented by the codes shown in Table 2.
[0077]
Table 2
[0078] Taking the compound of the following structural formula as an example.
Chemical Formula
[0079] When the structural formula is represented by the code shown in Table 2, it can be represented as nCCGF. In the code, n represents the number of C atoms of the alkyl group at the left end. For example, when n is "3", it means that the alkyl group is -C3H7. In the code, C represents a 1,4-cyclohexylene group, G represents a 2-fluoro-1,4-phenylene group, and F represents fluorine.
[0080] The abbreviations of the test items in the following examples are as follows. Cp Clearing point (nematic phase-isotropic phase transition temperature, °C) Δn Optical anisotropy (589 nm, 25 °C) ε ⊥ Vertical dielectric constant Δε Dielectric anisotropy (1 kHz, 25 °C) ε ⊥ / |Δε| Ratio of vertical dielectric constant to absolute value of dielectric constant T r Transmittance (%) K 11 Spray elastic constant K 33 Bend elastic constant τ off Time required for the transmittance to decrease from 90% to 10% when the power is turned off (ms, 25 °C) Cp: Obtained from tests using a melting point measuring device. Δn: Obtained by testing at 25 °C under the light source of a sodium lamp (589 nm) using an Abbe refractometer. Δε: Δε = ε ll -ε ⊥ where ε ll is the dielectric constant parallel to the molecular axis, and 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. T r : The V-T curve of the dimming device is tested using a DMS 505 optoelectronic integration test device. The maximum value of the transmittance in the V-T curve is taken as the transmittance of the liquid crystal. The test cell is of the negative IPS type and the cell thickness is 3.5 μm. K 11 and K 33 : Obtained by testing and calculating the C-V curve of the liquid crystal material using an LCR meter and a VA test cell. The test conditions are a cell thickness of 6 μm and V = 0.1 to 20 V. τ off : Obtained by testing using a DMS 505 liquid crystal display optical measurement system. The test conditions are a negative IPS type test cell with a cell thickness of 3.5 μm and 25 °C.
[0081] Each component adopted in the following examples can be synthesized by known methods or obtained through sales channels. These synthetic techniques are common, and each obtained liquid crystal compound meets the standards of electronic compounds through testing.
[0082] Prepare the liquid crystal composition according to the blending ratios of each liquid crystal composition defined in the following examples. The preparation of the liquid crystal composition is carried out by general methods in this field. For example, methods such as heating, ultrasonic waves, and suspension are adopted to mix according to the ratios for production.
[0083] Comparative Example 1 and Examples 1 - 4 Prepare the liquid crystal compositions of Comparative Example 1 and Examples 1 - 4 according to the compounds shown in Table 3 and their weight percentages, and fill them between two substrates of a liquid crystal display for performance testing.
[0084]
Table 3
[0085] As can be seen from the comparison between Comparative Example 1 and Examples 1 - 4, compared with the prior art, the liquid crystal composition containing the compounds of General Formula I and General Formula III of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an appropriate absolute value of dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance.
[0086] Comparative Example 2 and Examples 5 - 8 Prepare the liquid crystal compositions of Comparative Example 2 and Examples 5 - 8 according to the compounds shown in Table 4 and their weight percentages, and fill them between two substrates of a liquid crystal display for performance testing.
[0087]
Table 4
[0088] As can be seen from the comparison between Comparative Example 2 and Examples 5 to 8, compared with the prior art, the liquid crystal composition containing the compound of General Formula I and the compound of General Formula III of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an appropriate absolute value of dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance.
[0089] Comparative Example 3 and Examples 9 to 12 According to each compound shown in Table 5 and its weight percentage, the liquid crystal compositions of Comparative Example 3 and Examples 9 to 12 were prepared, and the same was filled between two substrates of a liquid crystal display to perform a performance test.
[0090]
Table 5
[0091] As can be seen from the comparison between Comparative Example 3 and Examples 9 to 12, compared with the prior art, the liquid crystal composition containing the compound of General Formula I and the compound of General Formula II of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an appropriate absolute value of dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance.
[0092] Comparative Example 4 and Examples 13 to 16 According to each compound shown in Table 6 and its weight percentage, the liquid crystal compositions of Comparative Example 4 and Examples 13 to 16 were prepared, and the same was filled between two substrates of a liquid crystal display to perform a performance test.
[0093]
Table 6
[0094] As can be seen from the comparison between Comparative Example 4 and Examples 13 to 16, compared with the prior art, the liquid crystal composition of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an absolute value of appropriate dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance.
[0095] Comparative Example 5 and Examples 17 to 20 According to each compound shown in Table 7 and its weight percentage, the liquid crystal compositions of Comparative Example 5 and Examples 17 to 20 were prepared, and the same was filled between two substrates of a liquid crystal display to perform a performance test.
[0096]
Table 7
[0097] As can be seen from the comparison between Comparative Example 5 and Examples 17 to 20, compared with the prior art, the liquid crystal composition of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an absolute value of appropriate dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance.
[0098] In summary, the liquid crystal composition of the present invention maintains an appropriate clearing point, appropriate optical anisotropy, and an absolute value of appropriate dielectric anisotropy, and further has a larger vertical dielectric constant, a larger ratio of the vertical dielectric constant to the absolute value of the dielectric constant, a larger K value, a shorter response time, and a higher transmittance. Thereby, the liquid crystal display device containing the same has better contrast, faster response speed, and better transmittance while maintaining an appropriate usable temperature range and an appropriate threshold voltage.
[0099] The above embodiments are only for explaining the technical ideas and features of the present invention so that those skilled in the art can understand and implement the content of the present invention, and do not limit the protection scope of the present invention. Any equivalent transformation or modification made based on the gist of the present invention should be included within the protection scope of the present invention.
Claims
1. At least one compound of general formula I, 【Chemical 1】 I a compound of general formula II, and a compound of general formula III, 【Chemical Formula 2】 II 【Chemical Formula 3】 III comprising, where R 2 , R 5 and R 6 are each independently a linear or branched alkyl group containing 1 to 12 carbon atoms 【Chemical 4】 、 【Chemical Formula 5】 or 【Chemical Formula 6】 represents, and one or two or more non-adjacent -CH of the linear or branched alkyl group containing 1 to 12 carbon atoms among them 2 - may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO- R1 represents a linear or branched alkenyl group containing 2 to 12 carbon atoms, or a linear or branched alkenyloxy group containing 2 to 11 carbon atoms, ring [Chemical Formula 7] and ring [Chemical Formula 8] each independently represents 【Chemical Formula 9】 or 【Chemical Formula 10】 wherein one or more of the -H in 【Chemical Formula 11】 one or more of -CH 2 - may be replaced by -O-, and one or more single bonds of the ring may be replaced by double bonds, 【Chemical 12】 may each independently be replaced by -F, -Cl, or -CN, and one or more of the -CH= in the ring may be replaced by -N=, R3 represents a linear or branched alkyl group containing 1 to 12 carbon atoms, 【Chemical Formula 13】 、 【Chemical 14】 or 【Chemical Formula 15】 represents, wherein one or two or more non-adjacent -CH2- in the linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO-, R4 is 【Chemical Formula 16】 、 【Chemical 17】 、 【Chemical Formula 18】 、 【Chemical Formula 19】 、 【Chemical 20】 、 【Chemical 21】 、 【Chemical 22】 , and 【Chemical 23】 selected from the groups represented by any of formulas (V1) to (V8) of Z 1 and Z 2 each independently represents a single bond, —CO—O—, —O—CO—, —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 —, and L 1 、 L 2 、 L 3 and L 4 each independently represents F, -Cl, -CF 3 , -OCF 3 or -CHF 2 and n 1 represents 0, 1, 2, or 3, and n 2 represents 0 or 1, and 0 < n 1 + n 2 ≤ 3, where when n 1 = 2 or 3, the ring 【Chemical 24】 may be the same or different, Z 1 may be the same or different, and ring 【Chemical 25】 and ring 【Chemical 26】 wherein at least one of the rings 【Chemical 27】 、 【Chemical Formula 28】 or 【Chemical 29】 represents, a liquid crystal composition characterized by this.
2. The compound of general formula I is 【Chemical 30】 I-1, 【Chemical Formula 31】 I-2, 【Chemical 32】 I-3, 【Chemical 33】 I-4, selected from the group consisting of the compounds of wherein a represents an integer from 0 to 4, and b represents an integer from 1 to 4, the liquid crystal composition according to Claim 1, characterized by this.
3. The liquid crystal composition according to Claim 2, characterized by containing at least one compound of general formula I-2.
4. The compound of general formula III is 【Chemical 34】 III-1, 【Chemical 35】 III-2, 【Chemical 36】 III-3, 【Chemical 37】 III-4, 【Chemical Formula 38】 III-5, 【Chemical 39】 III-6, 【Chemical 40】 III-7, 【Chemical 41】 III-8, 【Chemical 42】 III-9, 【Chemical 43】 III-10, 【Chemical 44】 III-11, 【Chemical 45】 III-12, 【Chemical 46】 III-13, 【Chemical 47】 III-14, 【Chemical 48】 III-15, 【Chemical 49】 III-16, 【Chemical Formula 50】 III-17, 【Chemical Formula 51】 III-18, 【Chemical 52】 III-19, 【Chemical 53】 III-20, 【Chemical 54】 III-21 selected from the group consisting of the compounds of, the liquid crystal composition according to Claim 1, characterized by this.
5. The liquid crystal composition according to Claim 1, characterized by containing at least one compound of general formula I and at least one compound of general formula III.
6. Further containing at least one compound of general formula M, 【Chemical Formula 55】 M Here, R M1 and R M2 each independently represents a linear or branched alkyl group containing 1 to 12 carbon atoms, 【Chemical Formula 56】 、 【Chemical 57】 or 【Chemical Formula 58】 represents, and one or two or more non-adjacent -CH of the linear or branched alkyl group containing 1 to 12 carbon atoms 2 - may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO- ring 【Chemical 59】 , ring 【Chemical Formula 60】 and ring 【Chemical Formula 61】 each independently represents 【Chemical Formula 62】 or 【Chemical 63】 wherein 【Chemical Formula 64】 one or more of -CH 2 - may be replaced by -O-, and one or more single bonds in the ring may be replaced by double bonds, 【Chemical Formula 65】 At most one of the -H may be replaced by a halogen, Z M1 and Z M2 each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-, -OCH 2 -, -C≡C-, -CH=CH-, -CH 2 CH 2 - or -(CH 2 ), 4 and represents n M represents 0, 1 or 2, where n M = 2, the ring 【Chemical Formula 66】 may be the same or different, Z M2 may be the same or different, and n M The liquid crystal composition according to claim 1, wherein when n represents 1 and the compound of the general formula M contains a bisbiphenyl structure, the terminal group bonded to the aromatic ring is not an alkenyl group or an alkenyloxy group.
7. In the liquid crystal composition, the weight percentage of the compound of the general formula I is 0.1% to 50%, and in the liquid crystal composition, the weight percentage of the compound selected from the group consisting of the compound of the general formula II, the compound of the general formula III, and combinations thereof is 0.1% to 50%, and in the liquid crystal composition, the weight percentage of the compound of the general formula M is 1% to 80%. The liquid crystal composition according to claim 6, characterized in that.
8. Further comprising at least one compound of the general formula N, 【Chemical 67】 N Here, R N1 and R N2 each independently represents a linear or branched alkyl group containing 1 to 12 carbon atoms, 【Chemical Formula 68】 、 【Chemical Formula 69】 or 【Chemical 70】 represents, and one or two or more non-adjacent -CH among the linear or branched alkyl groups containing 1 to 12 carbon atoms 2 - may each independently be replaced by -CH=CH-, -C≡C-, -O-, -CO-, -CO-O- or -O-CO- ring 【Chemical 71】 and ring 【Chemical 72】 are each independently, 【Chemical 73】 or 【Chemical 74】 represents, where 【Chemical 75】 One or more of -CH 2 - may be replaced by -O-, 【Chemical 76】 One or more of the -H may each independently be replaced by -F, -Cl, or -CN, and one or more of the -CH= of the ring may be replaced by -N=. Z N1 and Z N2 each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-, -OCH 2 -, -CH=CH-, -C≡C-, -CH 2 CH 2 -, -CF 2 CF 2 -, -(CH 2 ) 4 -, -CFO- or -OCF 2 -, and represents 2 L N1 and L N2 are each independently, -F, -Cl, -CF 3 , -OCF 3 or -CHF 2 and represent L N3 and L N4 each independently represents -H, an alkyl group containing 1 to 3 carbon atoms, or a halogen, n N1 represents 0, 1, 2, or 3, and n N2 represents 0 or 1, and 0 ≤ n N1 + n N2 ≤ 3, where when n N1 = 2 or 3, the ring 【Chemical Formula 77】 may be the same or different, Z N1 may be the same or different, and n N1 represents 2, n N2 represents 0, and when the compound of the general formula N contains a bisbiphenyl structure, R N1 is not an alkenyl group or an alkenyloxy group, The liquid crystal composition according to claim 1, characterized in that.
9. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 8.
Citation Information
Patent Citations
Liquid crystal compound
CN109593532A
Liquid crystal medium, stabilization method thereof and liquid crystal display
JP2014084462A
Liquid crystal composition and liquid crystal display element
JP2020002210A