WO2021134882A1 - Composition de cristaux liquides à grande constante élastique de composé cristallin liquide négatif ayant une liaison en pont méthoxy et utilisation associée - Google Patents

Composition de cristaux liquides à grande constante élastique de composé cristallin liquide négatif ayant une liaison en pont méthoxy et utilisation associée Download PDF

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Publication number
WO2021134882A1
WO2021134882A1 PCT/CN2020/077016 CN2020077016W WO2021134882A1 WO 2021134882 A1 WO2021134882 A1 WO 2021134882A1 CN 2020077016 W CN2020077016 W CN 2020077016W WO 2021134882 A1 WO2021134882 A1 WO 2021134882A1
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general formula
compound represented
liquid crystal
crystal composition
composition contains
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PCT/CN2020/077016
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English (en)
Chinese (zh)
Inventor
陈卯先
储士红
姜天孟
陈海光
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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Publication of WO2021134882A1 publication Critical patent/WO2021134882A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods

Definitions

  • 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.
  • either positive liquid crystal or negative liquid crystal can be used. Because the negative liquid crystal molecules are arranged perpendicular to the direction of the electric field line under the action of an electric field, compared to the positive liquid crystal molecules along the electric field under the action of the electric field The line direction is arranged and the use of negative polarity avoids the transmittance sacrifice and flicker problems caused by the bending electric field in the IPS and FFS modes, thereby improving the transmittance and flicker of the LCD.
  • the object of the present invention is to provide a liquid crystal composition with a large elastic constant to achieve the purpose of improving the contrast of liquid crystal displays, and at the same time, the liquid crystal composition has negative dielectric anisotropy and is used in liquid crystal displays It has a higher transmittance and has the effect of improving the flicker of the liquid crystal display.
  • the liquid crystal composition provided by the 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.
  • a liquid crystal composition with a large elastic constant containing a methoxy bridge bond negative liquid crystal compound comprising at least one or more compounds represented by general formula I, one or more compounds represented by general formula II, One or more compounds represented by general formula III and one or more compounds represented by general formula IV;
  • R 1 and R 2 each independently represent a C 1 to C 12 linear alkyl group, a linear alkoxy group or a C 2 to C 12 linear alkenyl group;
  • R 3 and R 4 each independently represent a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group; n 2 is 0 or 1. ;
  • the compound represented by the general formula I is the formula IA or 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 compounds represented by formulas IA1 to IA63 or formulas IB1 to IB45:
  • the compound represented by the general formula I is selected from one of IA3, IA12, IA21, IA23, IA24, IA25, IA39, IA43, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31 Or more; further preferably, the compound represented by the general formula I is selected from IA3, IA21, IA23, IA24, IA25, IA39, IA43, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31 Most preferably, the compound represented by the general formula I is selected from one of IA3, IA21, IA23, IA39, IB3, IB5, IB8, IB10, IB26, IB27, IB30, IB31 or Many kinds.
  • the compound represented by the general formula II is the formula IIA or IIB:
  • R 3 and R 4 are as defined above;
  • the compound represented by general formula II is selected from one or more of formula IIA1 to IIA42 or formula IIB1 to IIB42:
  • the compound represented by the general formula II is selected from one or more of IIA13, IIA17, IIA18, IIA20, IIB17, IIB18, and IIB20; most preferably, the compound represented by the general formula III is selected From one or more of IIA17, IIA18, IIB17, IIB18, and IIB20.
  • the compound represented by the general formula III is selected from one or more of the structures shown in formulas IIIA to IIIC:
  • R 5 and R 6 are as defined above;
  • the compound represented by general formula III is selected from one or more of the compounds represented by formulas IIIA1 to IIIA39, formulas IIIB1 to IIIB24, or formulas IIIC1 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; Most preferably, 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 above-mentioned liquid crystal composition further includes one or more compounds represented by the general formula IV:
  • R 7 and R 8 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 3 each independently represents Trans 1,4-cyclohexyl or 1,4-phenylene;
  • R 9 and R 10 each independently represent a C 1 ⁇ C 12 linear alkyl group, a linear alkoxy group or a C 2 ⁇ C 12 linear alkenyl group;
  • L 1 , L 2 , L 3 each independently represents H or F;
  • the compound represented by the general formula IV is the formula IVA or IVB:
  • R 7 and R 8 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 V is VA or VB:
  • R 9 each independently represents a C 1 ⁇ C 7 linear alkyl group or a C 2 ⁇ C 7 linear alkenyl group
  • R 10 each independently represents a C 1 ⁇ C 7 straight chain Alkyl or straight-chain alkoxy
  • the compound represented by the general formula IV is selected from one or more of the compounds represented by the general formulas IVA1 to IVA38 or formulas IVB1 to IVB38:
  • the compound represented by the general formula V is selected from one or more of the compounds represented by the formulas VA1 to VA24 or the formulas VB1 to VB24:
  • the compound represented by the general formula IV is selected from one of IVA3, IVA5, IVA8, IVA10, IVA26, IVA31, IVA33, IVA53, IVB3, IVB5, IVB8, IVB10, IVB13, IVB25, IVB30, IVB35.
  • the compound represented by the general formula IV is selected from one of IVA3, IVA8, IVA10, IVA26, IVA31, IVA33, IVA53, IVB3, IVB8, IVB13, IVB25, IVB30, IVB35 or Many kinds.
  • the above-mentioned liquid crystal composition further includes one or more compounds represented by the general formula VI:
  • R 11 and R 12 each independently represent a C 1 to C 12 linear alkyl group or a linear alkoxy group; n 3 is 0 or 1;
  • R 13 and R 14 each independently represent a C 1 -C 12 linear alkyl group;
  • L 4 represents H or F;
  • the compound represented by the general formula VI is the formula VIA or VIB:
  • R 11 each independently represents a C 1 ⁇ C 7 linear alkyl group
  • R 12 each independently represents a C 1 ⁇ C 7 linear alkyl group or a linear alkoxy group
  • the compound represented by the general formula VII is the formula VIIA or VIIB:
  • R 13 and R 14 each independently represent a C 1 -C 5 linear alkyl group
  • the compound represented by the general formula VI is selected from one or more of the compounds represented by the formula VIA1 to VIA24 or the formula VIB1 to VIB24:
  • the liquid crystal composition contains 1-15 wt% of the compound represented by the general formula I;
  • the liquid crystal composition contains 25 to 55 wt% of the compound represented by general formula II;
  • the liquid crystal composition contains 28 to 59 wt% of the compound represented by the general formula III;
  • the liquid crystal composition contains 3-12% by weight of the compound represented by the general formula I;
  • the liquid crystal composition contains 3-10% by weight of the compound represented by the general formula I;
  • the liquid crystal composition contains 29 to 48 wt% of the compound represented by the general formula II;
  • the liquid crystal composition contains 29 to 39 wt% of the compound represented by general formula II;
  • the liquid crystal composition contains 36 to 48 wt% of the compound represented by general formula II;
  • the liquid crystal composition contains 32 to 54 wt% of the compound represented by the general formula III;
  • the liquid crystal composition contains 38-52wt% of the compound represented by the general formula III;
  • the liquid crystal composition contains 33-50% by weight of the compound represented by the general formula III;
  • the liquid crystal composition contains 4-9wt% of the compound represented by the general formula I;
  • the liquid crystal composition contains 4-7 wt% of the compound represented by general formula I;
  • the liquid crystal composition contains 32-44 wt% of the compound represented by general formula II;
  • the liquid crystal composition contains 32-39wt% of the compound represented by the general formula II;
  • the liquid crystal composition contains 36-44 wt% of the compound represented by general formula II;
  • the liquid crystal composition contains 37 to 49 wt% of the compound represented by the general formula III;
  • the liquid crystal composition contains 37 to 47 wt% of the compound represented by the general formula III.
  • the present invention optimizes the percentage of each component in the provided liquid crystal composition.
  • liquid crystal composition of the present invention contains the following components by weight percentage: (1) 1-15% of the compound represented by the general formula I; (2) 25-55% of the compound represented by the general formula II; (3) 28 to 59% of compounds represented by general formula III; (4) 5 to 25% of compounds represented by general formulas IV to VII;
  • the liquid crystal composition includes the following components in weight percentage: (1) 3-12% of the compound represented by the general formula I; (2) 29-48% of the compound represented by the general formula II; (3) 32- 54% of the compound represented by the general formula III; (4) 8-20% of the compound represented by the general formula IV to VII; preferably, comprising: (1) 4-9% of the compound represented by the general formula I; (2) 32 to 44% of the compound represented by the general formula II; (3) 37 to 49% of the compound represented by the general formula III; (4) 10 to 16% of the compound represented by the general formula IV to VII;
  • the liquid crystal composition includes the following components by weight percentage: (1) 3-12% of the compound represented by the general formula I; (2) 29-39% of the compound represented by the general formula II; (3) 38- 52% of the compound represented by the general formula III; (4) 8-20% of the compound represented by the general formula IV to VII; preferably, comprising: (1) 4-9% of the compound represented by the general formula I; (2) 32 to 39% of compounds represented by general formula II; (3) 41 to 49% of compounds represented by general formula III; (4) 10 to 16% of compounds represented by general formulas IV to VII;
  • the liquid crystal composition includes the following components by weight percentage: (1) 3-10% of the compound represented by the general formula I; (2) 36-48% of the compound represented by the general formula II; (3) 33- 50% of the compound represented by the general formula III; (4) 8-20% of the compound represented by the general formula IV to VII; preferably, it contains: (1) 4 to 7% of the compound represented by the general formula I; (2) 36 to 44% of compounds represented by general formula II; (3) 37 to 47% of compounds represented by general formula III; (4) 12 to 16% of compounds represented by general formulas IV to VII.
  • the liquid crystal composition provided by the present invention increases the vertical dielectric of the liquid crystal composition by adding a type II compound, and improves the dielectric anisotropy through the type I compound, thereby obtaining a liquid crystal composition with a large vertical dielectric, and improving a liquid crystal display Transmittance. Through the optimized combination of the components, a liquid crystal composition with fast response and high transmittance is obtained.
  • 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
  • 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 constants (pN, 25°C).
  • Table 1 Group structure codes of liquid crystal compounds
  • the preparation of the liquid crystal composition adopts the thermal dissolution method, which includes the following steps: weigh the liquid crystal compound by weight percentage with a balance, wherein the order of weighing and addition is not specified, and the melting point of the liquid crystal compound is usually from high to low. Weigh and mix in sequence, heat and stir at 60-100°C to make the components melt uniformly, filter, rotatably, and finally package 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 20 Weight percentage and performance parameters of each component in the liquid crystal composition

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

La présente invention concerne une composition de cristaux liquides ayant une grande constante élastique d'un composé cristallin liquide négatif ayant une liaison en pont méthoxy et une utilisation associée. La composition de cristaux liquides comprend un ou plusieurs composés représentés par la formule générale I, un ou plusieurs composés représentés par la formule générale II et un ou plusieurs composés représentés par la formule générale III. La composition de cristaux liquides selon la présente invention a une grande constante élastique et un temps de réponse rapide, et peut améliorer le contraste d'un affichage à cristaux liquides lorsqu'elle est utilisée dans l'affichage à cristaux liquides. (I), (II), (III)
PCT/CN2020/077016 2020-01-03 2020-02-27 Composition de cristaux liquides à grande constante élastique de composé cristallin liquide négatif ayant une liaison en pont méthoxy et utilisation associée WO2021134882A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202010006365.0 2020-01-03
CN202010006365.0A CN113072955B (zh) 2020-01-03 2020-01-03 含有甲氧基桥键负性液晶化合物的具有大弹性常数的液晶组合物及其应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114806599A (zh) * 2022-05-20 2022-07-29 北京八亿时空液晶科技股份有限公司 一种具有大弹性常数的负性液晶组合物及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106010580A (zh) * 2016-05-25 2016-10-12 石家庄诚志永华显示材料有限公司 液晶组合物及其应用
EP3127991A1 (fr) * 2015-08-05 2017-02-08 Merck Patent GmbH Milieu cristallin liquide
CN107674686A (zh) * 2016-08-02 2018-02-09 石家庄诚志永华显示材料有限公司 液晶组合物
WO2018193859A1 (fr) * 2017-04-17 2018-10-25 Dic株式会社 Élément d'affichage à cristaux liquides
CN109837096A (zh) * 2017-11-24 2019-06-04 默克专利股份有限公司 液晶介质
CN109943347A (zh) * 2017-12-20 2019-06-28 石家庄诚志永华显示材料有限公司 液晶组合物及液晶显示元件

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3127991A1 (fr) * 2015-08-05 2017-02-08 Merck Patent GmbH Milieu cristallin liquide
CN106010580A (zh) * 2016-05-25 2016-10-12 石家庄诚志永华显示材料有限公司 液晶组合物及其应用
CN107674686A (zh) * 2016-08-02 2018-02-09 石家庄诚志永华显示材料有限公司 液晶组合物
WO2018193859A1 (fr) * 2017-04-17 2018-10-25 Dic株式会社 Élément d'affichage à cristaux liquides
CN109837096A (zh) * 2017-11-24 2019-06-04 默克专利股份有限公司 液晶介质
CN109943347A (zh) * 2017-12-20 2019-06-28 石家庄诚志永华显示材料有限公司 液晶组合物及液晶显示元件

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