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WO2021115155A1 - Composé à cristaux liquides, son procédé de préparation et son utilisation - Google Patents

Composé à cristaux liquides, son procédé de préparation et son utilisation Download PDF

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Publication number
WO2021115155A1
WO2021115155A1 PCT/CN2020/133008 CN2020133008W WO2021115155A1 WO 2021115155 A1 WO2021115155 A1 WO 2021115155A1 CN 2020133008 W CN2020133008 W CN 2020133008W WO 2021115155 A1 WO2021115155 A1 WO 2021115155A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
crystal compound
compound
carbon atoms
group
Prior art date
Application number
PCT/CN2020/133008
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English (en)
Chinese (zh)
Inventor
张海威
邓师勇
储士红
苏学辉
谢佩
戴雄
侯斌
姜坤
韩耀华
Original Assignee
北京八亿时空液晶科技股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication of WO2021115155A1 publication Critical patent/WO2021115155A1/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
    • 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0414—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a heterocyclic ring

Definitions

  • the invention belongs to the technical field of liquid crystal materials, and specifically relates to a liquid crystal compound and a preparation method and application thereof.
  • liquid crystal materials as environmental materials in the fields of information display materials and organic optoelectronic materials has great research value and bright application prospects.
  • 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 display information, no electromagnetic radiation, etc., which can almost meet the requirements of various information display, especially in TFT-LCD (thin film transistor technology) products aspect.
  • TFT active matrix system there are mainly TN (Twisted Nematic, twisted nematic structure) mode, IPS (In-Plane Switching, in-plane switching) mode, FFS (Fringe Field Switching, fringe field switching technology) mode and VA ( Main display modes such as Vertical Alignment (Vertical Alignment) mode.
  • TN Transmission Nematic, twisted nematic structure
  • IPS In-Plane Switching, in-plane switching
  • FFS Frringe Field Switching, fringe field switching technology
  • VA Main display modes such as Vertical Alignment (Vertical Alignment) mode.
  • TFT-LCD product technology has matured and successfully solved technical problems such as viewing angle, resolution, color saturation and brightness.
  • Large-size and medium- and small-size TFT-LCD displays have gradually occupied the mainstream status 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 the lowest possible rotational viscosity ⁇ 1.
  • 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 structural liquid crystal compounds and the study of the structure-performance relationship have become an important work in the field of liquid crystals.
  • the first object of the present invention is to provide a liquid crystal compound having a structure as shown in general formula (I):
  • R represents a trifluoromethyl group, a trifluoromethoxy group, a difluoromethoxy group, an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms, and the R represents 1-12 carbon atoms
  • one or more of the hydrogen atoms may be replaced by fluorine.
  • X represents O or S.
  • the structural formula of the liquid crystal compound is:
  • the R represents a trifluoromethyl group, a trifluoromethoxy group, a difluoromethoxy group, an alkyl group of 1 to 5 carbon atoms, or an alkoxy group.
  • the A represents -CH 2 O-
  • the R represents an alkoxy group with 2 or 3 carbon atoms.
  • the compound represented by the general formula (I) is selected from one of the following structures:
  • Another object of the present invention is to provide a preparation method of the liquid crystal compound of the present invention, the synthetic route is as follows:
  • R represents a trifluoromethyl group, a trifluoromethoxy group, a difluoromethoxy group, an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms, and the R represents 1-12 carbon atoms
  • one or more of the hydrogen atoms may be replaced by fluorine.
  • Another object of the present invention is to provide a composition including the liquid crystal compound of the present invention.
  • the mass percentage of the liquid crystal compound in the liquid crystal composition is 1 to 60%, preferably 3 to 50%, and more preferably 5 to 25%.
  • the last objective of the present invention is to protect the application of the liquid crystal compound of the present invention or the liquid crystal composition of the present invention in the field of liquid crystal display.
  • the liquid crystal display field is a liquid crystal display device.
  • the liquid crystal display device is a TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
  • the liquid crystal compound maintains large optical anisotropy ⁇ n, good rotational viscosity ⁇ 1, appropriate negative dielectric anisotropy ⁇ and liquid crystal mutual solubility, while having a higher clearing point Cp, which improves the liquid crystal composition
  • it also has good thermal stability, chemical stability, optical stability and mechanical properties; thereby effectively reducing the driving voltage and improving the response speed of the liquid crystal display device.
  • This embodiment relates to a liquid crystal compound, the structural formula of which is:
  • the resulting white solid BYLC-01 was analyzed by GC-MS, and the m/z of the product was 390.1 (M+).
  • This embodiment relates to a liquid crystal compound, the structural formula of which is:
  • the obtained white solid BYLC-02 was analyzed by GC-MS, and the m/z of the product was 360.1 (M+).
  • liquid crystal compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantial operations.
  • the structure of the compound involved in this comparative example is:
  • the structure of the compound involved in this comparative example is:
  • This experimental example involves the determination of the relevant properties of the compounds described in Examples 1 and 2 and the comparative example.
  • the detection of ⁇ is tested by an INSTEC liquid crystal detection instrument
  • the detection of ⁇ 1 is tested by a viscometer
  • the detection of ⁇ n is tested by an Abbe refractometer
  • the detection of Cp is tested by a differential calorimeter.
  • the performance parameters of the liquid crystal compound are obtained by linear fitting, and the specific meanings of the performance parameters are as follows:
  • the liquid crystal compound provided by the present invention is compared with the traditional negative dielectric anisotropy compound with similar chemical structure, the liquid crystal compound provided by the present invention maintains a large optical anisotropy ⁇ n , Good rotational viscosity ⁇ 1, appropriate negative dielectric anisotropy ⁇ , and a higher clearing point Cp, thereby effectively improving the clearing point of the liquid crystal composition, thereby shortening the response time of the liquid crystal display device and improving The working temperature of the liquid crystal composition.
  • the monomers of the present invention and the traditional structure monomers were mixed with BYLC-HJ-1000 (manufactured by BAYI Space-Time Liquid Crystal Technology Co., Ltd.) liquid crystals respectively in proportions, and then the storage conditions of the prepared samples at -20°C were examined, Above 240h can meet the requirements, below 240h does not meet the requirements, the test results are shown in Table 2;
  • N1-N5 represent the ratio grouping of the parent BYLC-HJ-1000 liquid crystal and the monomers of the present invention and the comparative example in the mixed liquid crystal under test.
  • the mutual solubility experiment shows that the compound used in the present invention has better mutual solubility than traditional liquid crystal compounds, can improve the mutual solubility of the liquid crystal composition, broaden the liquid crystal phase range of the liquid crystal composition, and increase the operating temperature range of the liquid crystal display.
  • the liquid crystal mixture is selected, and the liquid crystal model BYLC-HJ-1000 (manufactured by 800 million space-time liquid crystal technology Co., Ltd.) is used as the liquid crystal mixture.
  • the stability of the voltage holding rate of the liquid crystal mixture (BYLC-HJ-1000) itself is measured.
  • the liquid crystal mixture (BYLC-HJ-1000) itself is in a test box with a vertical alignment material and a flat ITO electrode. Cathode ((CCFL)-LCD backlight) illumination to study their stability to light.
  • test box was exposed to light for 1000 hours, and then the voltage retention rate was measured after 5 minutes at a temperature of 100°C under different conditions.
  • voltage retention rate was measured after 5 minutes at a temperature of 100°C under different conditions.
  • six test boxes were filled and studied for each single mixture, as shown The value is the average of six single values and their standard deviation, including the case where the standard deviation is less than the accuracy of the above-mentioned measured value.
  • test box obtained above was sealed and stored in a conventional laboratory heating box at 100°C for 120 hours, and the voltage retention rate was measured after 5 minutes at 100°C, 1V and 60Hz (VHR, heating, 120 hours).
  • Example 1 The compound of Example 1 (ie BYLC-01) was added to the liquid crystal mixture BYLC-HJ-1000 (manufactured by Bayi Space-Time Liquid Crystal Technology Co., Ltd.) at a ratio of 5% to obtain the mixture M-1.
  • Example 2 ie BYLC-02
  • Comparative Example 1 were added to the liquid crystal mixture BYLC-HJ-1000 (manufactured by Bayi Space Liquid Crystal Technology Co., Ltd.) to obtain mixtures M-2, M-3, and M, respectively.
  • -4 Study its stability according to the method described above, and the results are shown in the following table:
  • the VHR of the mixture using the compound provided by the present invention before exposure is better than the value of the starting mixture and the comparison example mixture, and the VHR does not change much after exposure, showing excellent thermal stability It has good stability against degradation of heat and UV exposure and a stable high VHR, which effectively reduces the probability of image delay, maintains a low threshold voltage, improves response time, and prolongs use. life.
  • the present invention provides a liquid crystal compound and a preparation method and application thereof.
  • the liquid crystal compound has a structure as shown in the general formula (I):
  • the liquid crystal compound of the present invention maintains large optical anisotropy ⁇ n, good rotational viscosity ⁇ 1, appropriate negative dielectric anisotropy ⁇ and liquid crystal mutual solubility, while having a higher clearing point Cp, which improves The working temperature of the liquid crystal composition; in addition, it also has good thermal stability, chemical stability, optical stability, and mechanical properties; thereby, it can effectively reduce the driving voltage, improve the response speed of the liquid crystal display device, and have better 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé à cristaux liquides, son procédé de préparation et son utilisation. Le composé à cristaux liquides présente une structure telle que représentée par la formule générale (I). Le composé à cristaux liquides présente un point de clarification Cp supérieur, tout en conservant une grande anisotropie optique △n, une bonne viscosité de rotation γ1, et une anisotropie diélectrique négative △ε appropriée et une miscibilité de cristaux liquides, provoquant ainsi une température de fonctionnement accrue d'une composition de cristaux liquides. De plus, le composé à cristaux liquides présente en outre de bonnes performances en termes de stabilité thermique, de stabilité chimique, de stabilité optique, de propriétés mécaniques, etc., et peut ainsi efficacement réduire une tension d'entraînement et accroître la vitesse de réponse d'un dispositif d'affichage à cristaux liquides.
PCT/CN2020/133008 2019-12-13 2020-12-01 Composé à cristaux liquides, son procédé de préparation et son utilisation WO2021115155A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201911286265.1 2019-12-13
CN201911286265.1A CN112980460A (zh) 2019-12-13 2019-12-13 一种液晶化合物及其制备方法和应用

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WO2021115155A1 true WO2021115155A1 (fr) 2021-06-17

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Publication number Priority date Publication date Assignee Title
CN114262323B (zh) * 2021-11-24 2023-09-08 西安近代化学研究所 一种负介电各向异性液晶化合物、组合物及显示元件

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US11214736B2 (en) * 2015-09-09 2022-01-04 Merck Patent Gmbh Liquid-crystalline medium
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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
CN106045953A (zh) * 2015-04-13 2016-10-26 默克专利股份有限公司 氟化的二苯并呋喃和二苯并噻吩的衍生物
CN110300746A (zh) * 2017-02-27 2019-10-01 捷恩智株式会社 具有二苯并呋喃环的化合物、液晶组合物及液晶显示元件
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
JP2019099515A (ja) * 2017-12-05 2019-06-24 Dic株式会社 液晶化合物及びその組成物
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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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CN112980460A (zh) 2021-06-18
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