WO2021134880A1 - Composition à cristaux liquides contenant une structure de 2-méthyl-3,4,5-trifluorobenzène et son utilisation - Google Patents

Composition à cristaux liquides contenant une structure de 2-méthyl-3,4,5-trifluorobenzène et son utilisation Download PDF

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WO2021134880A1
WO2021134880A1 PCT/CN2020/077005 CN2020077005W WO2021134880A1 WO 2021134880 A1 WO2021134880 A1 WO 2021134880A1 CN 2020077005 W CN2020077005 W CN 2020077005W WO 2021134880 A1 WO2021134880 A1 WO 2021134880A1
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general formula
compound represented
liquid crystal
crystal composition
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储士红
陈卯先
陈海光
姜天孟
未欣
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北京八亿时空液晶科技股份有限公司
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Definitions

  • the invention belongs to the field of liquid crystal compositions, and specifically relates to a liquid crystal composition containing a 2-methyl-3,4,5-trifluorobenzene structure.
  • LCD displays have been widely used in various products.
  • IPS and FFS mode displays are widely used in mobile phones, laptops, and tablets because of their unique hard screen characteristics and very wide viewing angle characteristics.
  • the present invention aims to provide a liquid crystal composition with a large elastic constant, so as to achieve the purpose of improving the contrast of the liquid crystal display.
  • the present invention finds that the liquid crystal composition provided by the present invention has a large elastic constant on the one hand, and a lower rotational viscosity on the other hand, thereby realizing a liquid crystal display with high contrast and fast response.
  • the liquid crystal composition of the present invention includes one or more compounds represented by the general formula I:
  • R 1 and R 2 each independently represent a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group;
  • the liquid crystal composition includes one or more compounds represented by general formula II:
  • a 2 each independently represents:
  • a 3 each independently represents:
  • the liquid crystal composition includes one or more compounds represented by the general formula III:
  • R 4 and R 5 each independently represent a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group, and A 4 , A 5 each independently represent a trans 1,4-cyclohexyl or 1,4-phenylene.
  • the compound of the general formula I provided by the present invention is a compound containing a cyclohexene structure. This type of compound has a large elastic constant and is very effective for improving the elastic constant of the liquid crystal composition.
  • the compound of general formula II provided by the present invention contains a compound in which a 2-methyl-3,4,5-trifluorobenzene structure is connected to a CF2O bridge bond. This type of compound has a very large dielectric anisotropy and a very large The dielectric anisotropy of the liquid crystal composition can effectively improve the dielectric anisotropy of the liquid crystal composition.
  • the compound of the general formula III provided by the present invention is a two-ring structure compound, and this type of compound has a very low
  • the rotational viscosity is very effective for reducing the rotational viscosity of the liquid crystal composition.
  • the combination of the above-mentioned substances can effectively improve the contrast and response speed of the liquid crystal display.
  • the compound represented by general formula I is selected from one or more of IA to IB:
  • R 1 and R 2 each independently represent a C 1 to C 7 linear alkyl group or a C 2 to C 7 linear alkenyl group;
  • the compound represented by the general formula I is selected from one or more of the formulas IA1 to IB45:
  • the compound of formula I is selected from one or more of IA3, IA12, IA21, IA23, IA24, IA25, IA39, IA43, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31 ;
  • the compound of formula I is selected from one or more of IA3, IA21, IA23, IA24, IA25, IA39, IA43, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31;
  • the compound of formula I is selected from one or more of IA3, IA21, IA23, IA39, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31;
  • the liquid crystal composition contains 1 to 35% of the compound of formula I by mass;
  • the mass percentage of the compound of general formula I is 2-30%, 2-14%, 10-30%, 5-18%, 2-28%, 5-28%, 5-25% or 2-26% ;
  • the mass percentage of the compound represented by the general formula I is 2-24%, 7-20%, 7-16%, 6-24%, 6-16%, 10-24% or 2-14%.
  • the compound represented by the general formula II is selected from one or more of IIA to IIM:
  • the compound represented by general formula II is selected from one or more of formula IIA1 to IIM5:
  • the compound of formula II is selected from formula IIA3, IIB2, IIB3, IIC2, IIC3, IID2, IID3, IIF3, IIG3, IIG4, IIH3, IIH4, IIH5, IIJ3, IIK2, IIK3, IIL3, IIM3, IIM4
  • formula IIA3, IIB2, IIB3, IIC2, IIC3, IID2, IID3, IIF3, IIG3, IIG4, IIH3, IIH4, IIH5, IIJ3, IIK2, IIK3, IIL3, IIM3, IIM4 One or more of
  • the compound of formula II is selected from one or more of formula IIB3, IIC2, IIC3, IID3, IIF3, IIG3, IIG4, IIH3, IIH4, IIH5, IIK3, IIL3, IIM3, IIM4;
  • the compound of formula II is selected from one or more of formula IIB3, IIC2, IIC3, IID3, IIG3, IIG4, IIH3, IIH4, IIH5, IIL3, IIM3, IIM4;
  • the liquid crystal composition contains 5-50% of the compound represented by general formula II;
  • the liquid crystal composition contains 8 to 37%, 8 to 40%, 8 to 35%, 15 to 40%, 8 to 21%, 8 to 38% of the compound represented by general formula II;
  • the liquid crystal composition contains 11 to 34%, 11 to 30%, 12 to 27%, 11 to 30%, 11 to 34%, 11 to 21%, 15 to 34%, 11 to 33%, 12 to 34% of the compound represented by general formula II.
  • the compound represented by the general formula III is selected from one or more of the formulas IIIA to IIIC:
  • R 4 each independently represents a C 1 ⁇ C 7 linear alkyl group
  • R 5 each independently represents a C 1 ⁇ C 7 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 7 straight chain Alkenyl
  • the compound represented by the general formula III is selected from one or more of the formulas IIIA1 to IIIC24:
  • the compound represented by the general formula III is selected from one or more of IIIA3, IIIA7, IIIA11, IIIA12, IIIA25, IIIA29, IIIA31, IIIA37, IIIB18, IIIB22, IIIC2, IIIC4, IIIC15, and IIIC20;
  • the compound represented by the general formula III is selected from one or more of IIIA25, IIIA29, IIIA37, IIIB18, IIIB22, IIIC2, IIIC4, IIIC15, and IIIC20;
  • the liquid crystal composition contains 10-75% of the compound represented by the general formula III;
  • the liquid crystal composition contains 20 to 70%, 30 to 70%, 20 to 50%, 30 to 50%, 20 to 65% of the compound represented by general formula III;
  • the liquid crystal composition contains 22 to 62%, 42 to 65%, 22 to 65%, 32 to 47%, 32 to 65%, and 22 to 47% of the compound represented by the general formula III.
  • the liquid crystal composition further includes one or more compounds represented by the general formula IV:
  • R 6 and R 7 each independently represent a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group;
  • a 6 each independently represents a trans 1,4 -Cyclohexyl or 1,4-phenylene;
  • the compound represented by the general formula IV is selected from one or more of IVA-IVB:
  • R 6 and R 7 each independently represent a C 1 to C 7 linear alkyl group, a linear alkoxy group, or a C 2 to C 7 linear alkenyl group.
  • the compound represented by the general formula IV is selected from one or more of IVA1 to IVB62:
  • the compound represented by formula IV is selected from one or more of IVA3, IVA5, IVA8, IVA10, IVA26, IVA31, IVA33, IVA53, IVB3, IVB5, IVB8, IVB10, IVB13, IVB25, IVB30, IVB35 Species
  • the compound of general formula IV provided by the present invention is selected from one or more of IVA3, IVA8, IVA10, IVA26, IVA31, IVA33, IVA53, IVB3, IVB8, IVB13, IVB25, IVB30, IVB35;
  • the liquid crystal composition contains 0-35% of the compound represented by general formula IV;
  • the liquid crystal composition contains 0-25%, 0-21%, 0-20%, 1-25%, 0-22%, 0-18% of the compound represented by general formula IV;
  • the liquid crystal composition contains 3-21%, 6-21%, 3-18% of the compound represented by the general formula IV.
  • liquid crystal composition of the present invention further includes one or more compounds represented by the general formula V:
  • R 8 each independently represents a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group
  • X 1 each independently represents F, CF 3 , OCF 3
  • L 1 and L 2 each independently represent H or F
  • a 7 each independently represents:
  • the compound represented by the general formula V is selected from one or more of VA to VK:
  • R 8 each independently represents a C 1 -C 7 linear alkyl group or a C 2 -C 7 linear alkenyl group
  • X1 each independently represents F, CF 3 or OCF 3 ;
  • R 8 each independently represents a C 1 -C 5 linear alkyl group or a C 2 -C 5 linear alkenyl group;
  • X1 each independently represents F, CF 3 or OCF 3 .
  • the liquid crystal composition further includes one or more compounds represented by the general formula VI:
  • R 9 and R 10 each independently represent F, a C 1 ⁇ C 12 linear alkyl group or a C 2 ⁇ C 12 linear alkenyl group;
  • the compound represented by the general formula VI is selected from one or more of VIA or VIB:
  • R 9 and R 10 each independently represent a C 1 to C 7 linear alkyl group or a C 4 to C 5 linear alkenyl group;
  • R 9 and R 10 each independently represent a C 1 to C 5 linear alkyl group or a C 4 to C 5 linear alkenyl group.
  • the liquid crystal composition of the present invention includes the following components in mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a very large elastic constant and is very effective for improving the contrast of a liquid crystal display.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and excellent low-temperature mutual solubility, and is very effective for improving the contrast of the liquid crystal display and broadening the low-temperature working range of the liquid crystal display.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and a large dielectric anisotropy, and is very effective for improving the contrast of the liquid crystal display and reducing the driving voltage of the liquid crystal display.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and a low rotational viscosity, and is very effective for improving the contrast of the liquid crystal display and improving the response time.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and a large dielectric anisotropy, and is very effective for improving the contrast of the liquid crystal display and reducing the driving voltage of the liquid crystal display.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and low rotational viscosity, and has very excellent stability. It is very effective for improving the contrast of liquid crystal displays and improving the response time. In addition, the liquid crystal display produced by the liquid crystal composition has very excellent Reliability.
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components by mass percentage:
  • liquid crystal composition provided by the present invention contains the following components in mass percentage:
  • the above-mentioned liquid crystal composition has a large elastic constant and a large dielectric anisotropy, and is very effective for improving the contrast of the liquid crystal display and reducing the driving voltage of the liquid crystal display.
  • the preparation method of the liquid crystal composition of the present invention is not particularly limited.
  • the conventional method can be used to mix two or more compounds for production, such as by mixing different components at high temperature and dissolving each other, wherein the liquid crystal is combined
  • the compound is dissolved in the solvent used for the compound and mixed, and then the solvent is distilled off under reduced pressure; or the liquid crystal composition of the present invention can be prepared according to a conventional method, such as mixing the smaller component in the higher It is obtained by dissolving in the main component with a large content at a temperature of high temperature, or dissolving each component in an organic solvent, such as acetone, chloroform or methanol, and then mixing the solution to remove the solvent.
  • an organic solvent such as acetone, chloroform or methanol
  • Another objective of the present invention is to protect the application of the liquid crystal composition of the present invention in LCD displays
  • the present invention increases the elastic constant of the liquid crystal composition by adding the compound represented by the general formula I, increases the dielectric anisotropy of the liquid crystal composition by increasing the compound of the general formula II, and increases the compound of the general formula III to reduce the rotational viscosity; the research of the present invention
  • the personnel found that the compound represented by the general formula I has a very large elastic constant and a low rotational viscosity, which can improve the elastic constant of the liquid crystal composition while maintaining the rotational viscosity unchanged, thereby meeting the high contrast required by liquid crystal displays. And the purpose of quick response.
  • percentages in the present invention are weight percentages; temperature units are degrees Celsius; ⁇ n represents optical anisotropy (25°C); ⁇ ⁇ and ⁇ ⁇ represent parallel and perpendicular dielectric constants (25°C, 1000 Hz) respectively; ⁇ represents the dielectric anisotropy (25°C, 1000Hz); ⁇ 1 represents the rotational viscosity (mPa.s, 25°C); Cp represents the clearing point (°C) of the liquid crystal composition; K 11 , K 22 , and K 33 represent respectively Spreading, twisting and bending elastic constant (pN, 25°C); Kavg represents the average elastic constant ((K 11 +K 22 +K 33 )/3, pN, 25°C)
  • Table 1 Group structure codes of liquid crystal compositions
  • the liquid crystal composition is prepared by the thermal dissolution method, which includes the following steps: weigh the liquid crystal composition by weight percentage with a balance, wherein the order of weighing and addition is not specified, and the melting point of the liquid crystal composition is usually from high to Weigh and mix in low order, heat and stir at 60-100°C to make the components melt uniformly, then filter, rotate and steam, and finally encapsulate to obtain the target sample.
  • Table 2 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 3 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 4 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 5 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 6 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 7 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 8 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 9 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 10 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 11 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 12 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 13 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 14 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 15 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 16 The weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 17 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 18 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 19 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 20 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 21 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 22 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 23 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 24 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 25 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 26 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 27 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 28 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 29 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 30 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 31 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 32 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 33 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 34 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 35 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 36 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 37 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 38 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 39 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 40 Weight percentages and performance parameters of each component in the liquid crystal composition
  • Table 41 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 42 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Table 43 Weight percentage and performance parameters of each component in the liquid crystal composition
  • Example 1 has a larger elastic constant compared with Comparative Example 1, and the elastic constant of Example 1 is increased by about 20%, that is, it can increase the contrast of about 20% when used in a liquid crystal display. .
  • the liquid crystal composition provided by the present invention has a large elastic constant, and when used in IPS and FFS mode displays, it can effectively improve the contrast of liquid crystal displays. Therefore, the IPS or FFS type TFT liquid crystal display device to which the liquid crystal composition provided by the present invention is applicable can improve the dark state light leakage problem of the liquid crystal display, can significantly improve the contrast of the liquid crystal display, and can improve the contrast characteristics of the IPS or FFS mode liquid crystal display .
  • the present invention provides a liquid crystal composition containing 2-methyl-3,4,5-trifluorobenzene structure.
  • the composition of the present invention includes one or more compounds represented by the general formula I:
  • the present invention increases the elastic constant of the liquid crystal composition by adding the compound represented by the general formula I, increases the dielectric anisotropy of the liquid crystal composition by increasing the compound of the general formula II, and increases the compound of the general formula III to reduce the rotational viscosity; the present invention finds
  • the compound represented by the general formula I has a very large elastic constant and a low rotational viscosity. It can improve the elastic constant of the liquid crystal composition while maintaining the rotational viscosity unchanged, thereby meeting the high contrast and fast speed requirements of liquid crystal displays.
  • the purpose of the response has good economic value and application prospects.

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  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
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  • Nonlinear Science (AREA)
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Abstract

La présente invention relève du domaine technique des compositions à cristaux liquides, et concerne en particulier une composition à cristaux liquides contenant une structure de 2-méthyl-3,4,5-trifluorobenzène. La composition selon la présente invention comprend un ou plusieurs composés représentés par la formule générale I : (I) un composé représenté par la formule générale II : (II) et un composé représenté par la formule générale III : (III). La présente invention augmente une constante élastique de la composition à cristaux liquides par ajout du composé représenté par la formule générale I, augmente l'anisotropie diélectrique de la composition à cristaux liquides par augmentation d'un composé de type formule générale II, et réduit la viscosité rotationnelle par augmentation du composé représenté par la formule générale III. De plus, il a été découvert selon la présente invention que le composé représenté par la formule générale I a une viscosité rotationnelle relativement faible tout en ayant une très grande constante élastique, et peut conserver la viscosité rotationnelle inchangée tout en améliorant la constante élastique de la composition à cristaux liquides, ce qui permet de satisfaire ainsi les exigences pour un affichage à cristaux liquides à contraste élevé et à réponse rapide.
PCT/CN2020/077005 2020-01-03 2020-02-27 Composition à cristaux liquides contenant une structure de 2-méthyl-3,4,5-trifluorobenzène et son utilisation WO2021134880A1 (fr)

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KR20210125922A (ko) 2020-04-09 2021-10-19 메르크 파텐트 게엠베하 액정 매질
CN116162463A (zh) * 2021-11-24 2023-05-26 江苏和成显示科技有限公司 一种液晶组合物及其应用

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EP0410756A1 (fr) * 1989-07-26 1991-01-30 Chisso Corporation Composés cyclohexényléthane
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