WO2021127949A1 - Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif - Google Patents

Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif Download PDF

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Publication number
WO2021127949A1
WO2021127949A1 PCT/CN2019/127697 CN2019127697W WO2021127949A1 WO 2021127949 A1 WO2021127949 A1 WO 2021127949A1 CN 2019127697 W CN2019127697 W CN 2019127697W WO 2021127949 A1 WO2021127949 A1 WO 2021127949A1
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WIPO (PCT)
Prior art keywords
compound
general formula
weight
parts
liquid crystal
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Application number
PCT/CN2019/127697
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English (en)
Chinese (zh)
Inventor
李承贺
储士红
陈卯先
王杰
陈海光
姜天孟
Original Assignee
北京八亿时空液晶科技股份有限公司
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Application filed by 北京八亿时空液晶科技股份有限公司 filed Critical 北京八亿时空液晶科技股份有限公司
Priority to CN201980102835.9A priority Critical patent/CN114787318A/zh
Priority to JP2022537777A priority patent/JP2023508301A/ja
Priority to PCT/CN2019/127697 priority patent/WO2021127949A1/fr
Publication of WO2021127949A1 publication Critical patent/WO2021127949A1/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
    • C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters

Definitions

  • the invention belongs to the technical field of liquid crystal materials, and specifically relates to a liquid crystal composition capable of adapting to a wide operating temperature and its application in a liquid crystal display device.
  • a liquid crystal display is a display that uses liquid crystal as its material.
  • Liquid crystal is an organic compound between solid and liquid. It will become a transparent liquid when heated, and will become a crystalline turbid solid after cooling. Under the action of an electric field, the arrangement of the liquid crystal molecules will change, which will affect the change of light passing through it. This change of light can be expressed as a change of light and dark through the action of the polarizer. In this way, people finally control the light and dark changes through the control of the electric field, so as to achieve the purpose of displaying images.
  • liquid crystal composition provided by the present invention has the characteristics of high clearing point while having large optical anisotropy, and realizes the effect of effectively increasing the working temperature range.
  • the present invention provides a liquid crystal composition with large optical anisotropy and a wide temperature range and its application in a liquid crystal display device.
  • the liquid crystal composition of the present invention is a nematic liquid crystal composition, which not only has large optical anisotropy, but also has a high clearing point, which can effectively increase the working temperature range.
  • a liquid crystal composition capable of adapting to a wide operating temperature.
  • the raw material components include the following compounds in parts by weight:
  • a compound of general formula V 1-40 parts by weight
  • a compound of general formula VI 1-40 parts by weight;
  • R 1 and R 2 each independently represent an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms;
  • R 3 and R 4 each independently represent an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms;
  • R 5 represents an alkoxy group with 1-7 carbon atoms
  • R 6 represents an alkyl group with 1-7 carbon atoms or an alkenyl group with 2-7 carbon atoms
  • R 7 represents an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms
  • R 8 represents an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms
  • R 9 and R 10 each independently represent an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms;
  • R 11 represents an alkoxy group with 1-7 carbon atoms
  • R 12 represents an alkyl group with 1-7 carbon atoms or an alkenyl group with 2-7 carbon atoms;
  • R 13 and R 14 each independently represent an alkyl group of 1-7 carbon atoms or an alkenyl group of 2-7 carbon atoms.
  • raw material components of the liquid crystal composition include the following compounds in parts by weight:
  • raw material components of the liquid crystal composition include the following compounds in parts by weight:
  • a compound of general formula V 10-20 parts by weight
  • a compound of general formula VI 8-25 parts by weight
  • raw material components of the liquid crystal composition include the following compounds in parts by weight:
  • a compound of general formula IV 8 parts by weight
  • a compound of general formula VI 12 parts by weight
  • the compound of the general formula I is a compound containing an alkynyl group, which has a fast response speed; the compound of the general formula I is selected from one or more of the compounds represented by the following formula IA-formula ID Species:
  • the compound of the general formula II is a compound containing an alkynyl group and fluorine, and the compound has a fast response speed.
  • the compound of general formula II is selected from one or more of the following compounds represented by formula IIA-formula IIC:
  • the compound of the general formula III is a compound containing a two-ring structure, and the compound has good low-temperature miscibility; the compound of the general formula III is selected from one of the following compounds represented by the following formula IIIA-formula IIIE Or several:
  • the compound of the general formula IV is a compound containing a two-ring structure, and the compound has a large positive dielectric anisotropy; the compound of the general formula IV is selected from the following compounds represented by the following formula IVA-formula IVD One or more:
  • the compound of the general formula V is a compound containing a tricyclic cyano group structure, which has a relatively high clearing point and large positive dielectric anisotropy; the compound of the general formula V is selected from the following formula VA- One or more of the compounds represented by formula VD:
  • the compound of the general formula VI is a compound containing a two-cyclic ester structure, and the compound has good low-temperature miscibility.
  • the compound of the general formula VI is selected from one or more of the compounds represented by the following formula VIA-formula VIC:
  • the compound of the general formula VII is a compound containing a two-cyclic ester structure, and the compound has good low-temperature miscibility.
  • the compound of general formula VII is selected from one or more of the following compounds represented by formula VIIA-formula VIIE:
  • the compound of the general formula VIII is a compound containing a tetracyclic structure, and the compound has a high clearing point.
  • the compound of the general formula VIII is selected from one or more of the compounds represented by the following formula VIIIA-Formula VIIIF:
  • the raw material components of the liquid crystal composition further include 0.1-0.5 parts by mass of an ultraviolet absorber.
  • the ultraviolet absorber is one or a mixture of benzotriazoles, benzophenones, triazines, and benzoic acid esters.
  • the raw material components of the liquid crystal composition further include 0.01-0.05 parts by mass of antioxidant.
  • the antioxidant is one or more mixtures of hindered phenols, phosphites, and a complex type of hindered phenols and phosphites.
  • the preparation method of the liquid crystal composition includes the following steps: take each raw material component, add in order of melting point from high to low, dissolve under heating and stirring conditions, mix well, and filter and remove impurities to obtain The liquid crystal composition.
  • the heating temperature is 60-100°C.
  • the preparation method of the liquid crystal composition of the present invention is not particularly limited.
  • a conventional method can be used to mix two or more compounds for production, such as a method of mixing different components at a high temperature of 60-100°C and dissolving each other, wherein , The liquid crystal composition 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 combining a smaller content It is obtained by dissolving the components in the main components with larger content at a higher 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
  • the liquid crystal composition of the present invention adopts a compound of general formula I, a compound of general formula II, a compound of general formula III, a compound of general formula IV, a compound of general formula V, and a compound of general formula VI.
  • the compound, the compound of the general formula VII, and the compound of the general formula VIII are used as raw materials and appropriately proportioned.
  • the final prepared liquid crystal composition contains polycyclic, alkynyl, alkynyl cyano and ester-based compounds at the same time. High-definition bright spots, large optical anisotropy characteristics, and a wide operating temperature range, can adapt to high-temperature environmental conditions.
  • the liquid crystal composition of the present invention can be applied to various display devices, and is especially suitable for PDLC devices.
  • the liquid crystal composition is prepared by the thermal dissolution method, including the following steps: weigh the liquid crystal compound by weight percentage with a balance, wherein there is no specific requirement for the order of weighing and adding, and usually the liquid crystal compound has a melting point 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 encapsulate to obtain the target sample.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the first embodiment.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the embodiment 1.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the first embodiment.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the embodiment 1.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the first embodiment.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the first embodiment.
  • the preparation method of the liquid crystal compound described in this embodiment is the same as that of the embodiment 1.
  • Embodiment 1 The difference between this embodiment and Embodiment 1 is only that the raw material components also include the ultraviolet absorber V001, and the preparation methods of other raw material components and the liquid crystal compound are the same as those of Embodiment 1.
  • Component Compound code Weight (g) I 3CPTP2 6 II 3PPTU2 20 II 3PPTU4 10 II 3PPTU5 10 III 3CPO1 3 IV 3PZGCN 8 V 2CPZGCN 4 V 3CPZGCN 4 V 4CPZGCN 4 V 5CPZGCN 4 VI 3PZP5 12 VII 5CZPO2 12 VIII 3CCZPC3 3 —— UV absorber V001 0.3
  • the raw material components also include hindered phenolic antioxidant 0001, and the preparation methods of other raw material components and the liquid crystal compound are the same as those of Embodiment 1.
  • the preparation method of the liquid crystal compound in this comparative example is the same as that of Example 1.
  • the present invention is not limited to the above-mentioned best embodiment. Under the enlightenment of the present invention, anyone can derive other products in various forms, but regardless of any changes in its shape or structure, any product that is the same or similar to the present application Approximate technical solutions fall within the protection scope of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (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 pouvant être adaptée à des températures de fonctionnement relativement larges et son procédé de préparation. Le procédé de préparation implique l'utilisation d'un composé de formule générale (I), d'un composé de formule générale (II), d'un composé de formule générale (III), d'un composé de formule générale (IV), d'un composé de formule générale (V), d'un composé de formule générale (VI), d'un composé de formule générale (VII) et d'un composé de formule générale (VIII) comme matières premières et leur malaxage sous un rapport approprié pour préparer finalement la composition de cristaux liquides. La composition liquide contient en outre des composés polycycliques, alcynyle, cyano et ester, présente les propriétés d'un point de dégagement élevé et une grande anisotropie optique, et présente une plage de températures de fonctionnement relativement larges et peut s'adapter aux conditions d'environnement à haute température. La composition de cristaux liquides peut être appliquée à divers dispositifs d'affichage, spécialement des dispositifs PDLC.
PCT/CN2019/127697 2019-12-24 2019-12-24 Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif WO2021127949A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201980102835.9A CN114787318A (zh) 2019-12-24 2019-12-24 一种能适应较宽工作温度的液晶组合物及在器件中的应用
JP2022537777A JP2023508301A (ja) 2019-12-24 2019-12-24 比較的広い動作温度に適応できる液晶組成物及びデバイスにおける用途
PCT/CN2019/127697 WO2021127949A1 (fr) 2019-12-24 2019-12-24 Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2019/127697 WO2021127949A1 (fr) 2019-12-24 2019-12-24 Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif

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CN (1) CN114787318A (fr)
WO (1) WO2021127949A1 (fr)

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WO2010022891A1 (fr) * 2008-08-29 2010-03-04 Merck Patent Gmbh Milieu cristallin liquide et écran à cristaux liquides
CN102660298A (zh) * 2012-05-16 2012-09-12 河北迈尔斯通电子材料有限公司 一种智能电网电表用混合液晶材料
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CN105038813A (zh) * 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 液晶组合物
JP6044826B2 (ja) * 2012-09-21 2016-12-14 Dic株式会社 ネマチック液晶組成物
CN108624335A (zh) * 2017-03-15 2018-10-09 北京八亿时空液晶科技股份有限公司 一种液晶材料及其应用

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WO1997029167A1 (fr) * 1996-02-09 1997-08-14 Chisso Corporation Composition de cristaux liquides et element d'affichage associe
DE102004039276B4 (de) * 2003-09-19 2013-03-07 Merck Patent Gmbh Nematische Flüssigkristallmischung und deren Verwendung in Anzeigen
KR101572257B1 (ko) * 2006-08-25 2015-11-26 메르크 파텐트 게엠베하 액정 매질
CN103320143B (zh) * 2013-06-05 2015-07-15 江苏和成显示科技股份有限公司 液晶组合物及其应用

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Publication number Priority date Publication date Assignee Title
WO2010022891A1 (fr) * 2008-08-29 2010-03-04 Merck Patent Gmbh Milieu cristallin liquide et écran à cristaux liquides
CN101372619A (zh) * 2008-10-17 2009-02-25 江苏和成化学材料有限公司 一种stn液晶组合物
CN102660298A (zh) * 2012-05-16 2012-09-12 河北迈尔斯通电子材料有限公司 一种智能电网电表用混合液晶材料
JP6044826B2 (ja) * 2012-09-21 2016-12-14 Dic株式会社 ネマチック液晶組成物
CN102994101A (zh) * 2012-10-11 2013-03-27 江苏和成显示科技股份有限公司 液晶组合物
CN103351881A (zh) * 2013-06-18 2013-10-16 江苏和成显示科技股份有限公司 低介电频率依赖性液晶组合物及包含该组合物的pm显示器
CN105038813A (zh) * 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 液晶组合物
CN108624335A (zh) * 2017-03-15 2018-10-09 北京八亿时空液晶科技股份有限公司 一种液晶材料及其应用

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CN114787318A (zh) 2022-07-22

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