WO2022000982A1 - Composé de cristaux liquides contenant une structure dibenzothiophène et utilisation associée - Google Patents

Composé de cristaux liquides contenant une structure dibenzothiophène et utilisation associée Download PDF

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Publication number
WO2022000982A1
WO2022000982A1 PCT/CN2020/133014 CN2020133014W WO2022000982A1 WO 2022000982 A1 WO2022000982 A1 WO 2022000982A1 CN 2020133014 W CN2020133014 W CN 2020133014W WO 2022000982 A1 WO2022000982 A1 WO 2022000982A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
crystal compound
molar ratio
described step
reaction
Prior art date
Application number
PCT/CN2020/133014
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English (en)
Chinese (zh)
Inventor
朱波
姜卫东
冯静
戴雄
边坤
孙建波
姜坤
谢佩
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
Publication of WO2022000982A1 publication Critical patent/WO2022000982A1/fr

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Classifications

    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • 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

  • the invention relates to a liquid crystal compound and its application field, in particular to a liquid crystal compound containing a dibenzothiophene structure and its application.
  • liquid crystal materials As environmental materials, liquid crystal materials have great research value and bright application prospects in the fields of information display materials and organic optoelectronic materials. Liquid crystal materials have many advantages as new display materials, such as extremely low power consumption and low driving voltage. At the same time, compared with other materials, it also has the advantages of small size, light weight, long life, large amount of displayed information, no electromagnetic radiation, etc. It can almost meet the requirements of various information display, especially in TFT-LCD (Thin Film Transistor Technology) products aspect.
  • TFT-LCD Thin Film Transistor Technology
  • TFT active matrix system there are mainly TN (Twisted Nematic, twisted nematic structure) mode, IPS (In-Plane Switching, plane switching) mode, FFS (Fringe Field Switching, fringe field switching technology) mode and VA ( Vertical Alignment, vertical orientation) mode and other main display modes.
  • TN Transmission Nematic, twisted nematic structure
  • IPS In-Plane Switching, plane switching
  • FFS Frringe Field Switching, fringe field switching technology
  • VA Vertical Alignment, vertical orientation
  • TFT-LCD product technology has matured, successfully solving technical problems such as viewing angle, resolution, color saturation and brightness.
  • Large- and small-sized TFT-LCD displays have gradually occupied the mainstream position of flat-panel displays in their respective fields.
  • the liquid crystal material is required to have a fast response speed, so the liquid crystal material is required to have as low a rotational viscosity ⁇ 1 as possible.
  • the driving voltage of the liquid crystal needs to be as low as possible, so it is required to increase the dielectric anisotropy ⁇ of the liquid crystal.
  • Liquid crystal materials are the core functional materials of liquid crystal display devices.
  • liquid crystal materials are required to have a wide range of performance parameters, especially to reduce the rotational viscosity of liquid crystal materials. ⁇ 1 and increase the dielectric anisotropy ⁇ of the liquid crystal material.
  • the synthesis of new liquid crystal compounds and the study of structure-property relationship have become an important work in the field of liquid crystals.
  • the first objective of the present invention is to provide a liquid crystal compound containing a dibenzothiophene structure, so as to improve the deficiencies of existing liquid crystal materials and enhance the application value of such liquid crystal compounds.
  • the liquid crystal compound of the present invention has the structure represented by the general formula I or the general formula II:
  • a 1 represents a single bond or one of the following groups:
  • a 2 represents a single bond or one of the following groups:
  • a and b each independently represent 0, 1 or 2.
  • liquid crystal compound is selected from one of the following compounds:
  • the liquid crystal compound is selected from one of the following compounds:
  • the second object of the present invention is to provide a method for preparing the liquid crystal compound.
  • the preparation method includes the following steps:
  • step 1) As the optimization of the above technical solution, in the step 1), and The feeding molar ratio is 0.9 ⁇ 1.5:1.0;
  • step 2) The molar ratio of the feed to trifluoromethanesulfonic anhydride is 0.1-0.3:0.1-0.5;
  • the molar ratio of mercaptopropionate to ethyl mercaptopropionate is 0.1-0.3:0.1-0.3;
  • the feeding molar ratio with alkali is 0.1 ⁇ 1.0:1.0.
  • the preparation method includes the following steps:
  • step 1) As the optimization of the above technical solution, in the step 1), and The feeding molar ratio is 0.9 ⁇ 1.5:1.0;
  • the molar ratio of the feed to trifluoromethanesulfonic anhydride is 0.1-0.3:0.1-0.5;
  • the molar ratio of mercaptopropionate to ethyl mercaptopropionate is 0.1-0.3:0.1-0.3;
  • the feeding molar ratio with alkali is 0.1 ⁇ 1.0:1.0.
  • reaction raw materials can be synthesized through public commercial routes or methods known in the literature.
  • the method of the present invention may involve conventional post-treatment when necessary, and the conventional post-treatment is specifically as follows: extraction with dichloromethane, ethyl acetate or toluene, liquid separation, washing with water, drying, and evaporation on a vacuum rotary evaporator, the obtained
  • the product can be purified by vacuum distillation or recrystallization and/or chromatographic separation.
  • the liquid crystal compound of the present invention can be obtained stably and efficiently.
  • the third object of the present invention is to provide a liquid crystal composition containing the above-mentioned liquid crystal compound.
  • the mass percentage of the liquid crystal compound in the liquid crystal composition is 1-60%; preferably 3-50%; more preferably 5-25%.
  • the fourth object of the present invention is to provide the application of the above-mentioned liquid crystal compound and/or the above-mentioned liquid crystal composition in the field of liquid crystal display; preferably in the application of liquid crystal display device, the liquid crystal display device includes but is not limited to TN, ADS, VA , PSVA, FFS or IPS LCD monitor.
  • the main chemical structure is dibenzothiophene, and the dielectric anisotropy of such a structure itself is relatively large.
  • the introduction of fluorine atoms into the 4th and 6th positions of thiophene forms a strong synergistic effect, which makes the liquid crystal compound have extremely high negative dielectric anisotropy, and at the same time significantly improves the clearing point, relatively high optical anisotropy, moderate rotational viscosity and Liquid crystal mutual solubility, excellent performance at low temperature, good thermal stability, chemical stability, optical stability and mechanical properties; thus effectively reducing the driving voltage, improving the response speed of the liquid crystal display device, and having a charge retention rate Advanced features.
  • the raw materials can be obtained from open commercial sources unless otherwise specified.
  • a liquid crystal compound containing a dibenzothiophene structure, its structural formula is:
  • Example 1 the following liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations:
  • Example 1 the following liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations:
  • Example 1 the following liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations:
  • Example 1 the following liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations:
  • Example 1 the following liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations:
  • the liquid crystal compounds provided by the present invention maintain a large optical anisotropy ⁇ n, good rotational viscosity ⁇ 1 and At the same time of mutual solubility of liquid crystal, it has higher negative dielectric anisotropy ⁇ and significantly higher clearing point Cp, thereby effectively improving the negative dielectric anisotropy of liquid crystal composition, improving the response time, and improving the liquid crystal composition. Operating temperature.
  • the present invention provides a liquid crystal compound, especially a liquid crystal compound containing a dibenzothiophene structure and an application thereof; the liquid crystal compound has a structure represented by general formula I or general formula II:
  • the compound has extremely high negative dielectric anisotropy, and at the same time significantly improves the clearing point, relatively high optical anisotropy, moderate rotational viscosity and liquid crystal mutual solubility, excellent performance at low temperature, good thermal stability, chemical stability Therefore, it can effectively reduce the driving voltage and improve the response speed of the liquid crystal display device. At the same time, it has the characteristics of high charge retention rate, and has good economic value and application prospects.

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

Abstract

L'invention concerne un composé de cristaux liquides et son champ d'application, et concerne en particulier un composé de cristaux liquides contenant une structure de dibenzothiophène et son utilisation. Le composé de cristaux liquides a une structure telle que représentée par la formule générale I ou la formule générale II; et le composé a une anisotropie diélectrique négative extrêmement élevée et améliore également significativement le point de TC, présente une anisotropie optique relativement élevée, une viscosité rotationnelle modérée et une intersolubilité des cristaux liquides, présente d'excellents effets de travail à basse température, présente de bonnes propriétés de stabilité thermique, de stabilité chimique, de stabilité optique et mécanique, etc, ce qui permet de réduire efficacement une tension de commande, d'améliorer la vitesse de réponse d'un dispositif d'affichage à cristaux liquides, et d'avoir également des caractéristiques telles qu'un taux de rétention de charge élevé.
PCT/CN2020/133014 2020-07-01 2020-12-01 Composé de cristaux liquides contenant une structure dibenzothiophène et utilisation associée WO2022000982A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202010626287.4 2020-07-01
CN202010626287.4A CN113881443A (zh) 2020-07-01 2020-07-01 一种含有二苯并噻吩结构的液晶化合物及其应用

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WO2022000982A1 true WO2022000982A1 (fr) 2022-01-06

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CN (1) CN113881443A (fr)
TW (1) TW202202488A (fr)
WO (1) WO2022000982A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115216305A (zh) * 2021-04-15 2022-10-21 江苏和成显示科技有限公司 液晶组合物及其液晶显示器件
CN118146805A (zh) * 2022-12-06 2024-06-07 北京八亿时空液晶科技股份有限公司 一种二苯噻吩液晶化合物及其制备方法与应用

Citations (9)

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CN105153112A (zh) * 2014-04-22 2015-12-16 默克专利股份有限公司 4,6-二氟二苯并噻吩衍生物
CN108264498A (zh) * 2017-08-16 2018-07-10 石家庄诚志永华显示材料有限公司 化合物、包含该化合物的液晶介质及其应用
CN109423296A (zh) * 2017-08-24 2019-03-05 北京八亿时空液晶科技股份有限公司 一种二苯并噻吩类负介电各向异性化合物及其制备方法和应用
TW201925435A (zh) * 2017-11-30 2019-07-01 日商捷恩智股份有限公司 具有二苯並噻吩環的化合物、液晶組成物及液晶顯示元件
JP2019147859A (ja) * 2018-02-26 2019-09-05 Jnc株式会社 液晶組成物および液晶表示素子
WO2020089140A1 (fr) * 2018-10-31 2020-05-07 Merck Patent Gmbh Dérivés de dibenzofurane et de dibenzothiophène
CN111170827A (zh) * 2018-11-13 2020-05-19 Dic株式会社 化合物、组合物和液晶显示元件
WO2020127172A1 (fr) * 2018-12-19 2020-06-25 Merck Patent Gmbh Milieu cristallin liquide et afficheur à cristaux liquides comprenant celui-ci et composés
CN111732569A (zh) * 2019-03-25 2020-10-02 捷恩智株式会社 具有二苯并噻吩环的液晶性化合物、液晶组合物及液晶显示元件

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153112A (zh) * 2014-04-22 2015-12-16 默克专利股份有限公司 4,6-二氟二苯并噻吩衍生物
CN108264498A (zh) * 2017-08-16 2018-07-10 石家庄诚志永华显示材料有限公司 化合物、包含该化合物的液晶介质及其应用
CN109423296A (zh) * 2017-08-24 2019-03-05 北京八亿时空液晶科技股份有限公司 一种二苯并噻吩类负介电各向异性化合物及其制备方法和应用
TW201925435A (zh) * 2017-11-30 2019-07-01 日商捷恩智股份有限公司 具有二苯並噻吩環的化合物、液晶組成物及液晶顯示元件
JP2019147859A (ja) * 2018-02-26 2019-09-05 Jnc株式会社 液晶組成物および液晶表示素子
WO2020089140A1 (fr) * 2018-10-31 2020-05-07 Merck Patent Gmbh Dérivés de dibenzofurane et de dibenzothiophène
CN111170827A (zh) * 2018-11-13 2020-05-19 Dic株式会社 化合物、组合物和液晶显示元件
WO2020127172A1 (fr) * 2018-12-19 2020-06-25 Merck Patent Gmbh Milieu cristallin liquide et afficheur à cristaux liquides comprenant celui-ci et composés
CN111732569A (zh) * 2019-03-25 2020-10-02 捷恩智株式会社 具有二苯并噻吩环的液晶性化合物、液晶组合物及液晶显示元件

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CN113881443A (zh) 2022-01-04
TW202202488A (zh) 2022-01-16

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