WO2021253621A1 - 液晶组合物、液晶显示元件、液晶显示器 - Google Patents

液晶组合物、液晶显示元件、液晶显示器 Download PDF

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WO2021253621A1
WO2021253621A1 PCT/CN2020/110963 CN2020110963W WO2021253621A1 WO 2021253621 A1 WO2021253621 A1 WO 2021253621A1 CN 2020110963 W CN2020110963 W CN 2020110963W WO 2021253621 A1 WO2021253621 A1 WO 2021253621A1
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liquid crystal
carbon atoms
crystal composition
group
formula
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PCT/CN2020/110963
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English (en)
French (fr)
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邢文晓
崔青
温刚
康素敏
翟媛媛
李吉凯
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石家庄诚志永华显示材料有限公司
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Publication of WO2021253621A1 publication Critical patent/WO2021253621A1/zh

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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

Definitions

  • the present invention belongs to the field of liquid crystal display, and more specifically, relates to a liquid crystal composition with negative dielectric anisotropy and a liquid crystal display element and a liquid crystal display containing the liquid crystal composition.
  • Liquid crystal display elements are divided into the following modes according to the display mode: twisted nematic (TN) mode, super twisted nematic (STN) mode, in-plane switching mode (IPS) or fringe field control mode (FFS), vertical alignment (VA) model.
  • the liquid crystal composition needs to have suitable optical anisotropy ⁇ n, suitable dielectric anisotropy ⁇ , low rotational viscosity ⁇ 1 , light and thermal stability, and good low-temperature storage performance.
  • liquid crystal material used in the display device it is required to have a fast response: a higher optical anisotropy ⁇ n, in order to match a lower cell thickness to achieve the same retardation ⁇ nd design; a lower rotational viscosity ⁇ 1 and high elastic coefficient K; 2High reliability: high charge retention rate, high specific resistance value, excellent high temperature stability and anti-aging performance against UV light or backlight.
  • a liquid crystal composition that has both fast response and good high temperature stability is an urgent problem to be solved.
  • the liquid crystal composition provided by the present invention has higher optical anisotropy ( ⁇ n) and lower rotational viscosity ⁇ 1 /elastic constant K on the basis of maintaining suitable electrical anisotropy ( ⁇ ).
  • ⁇ n optical anisotropy
  • ⁇ 1 /elastic constant K rotational viscosity
  • VHR thermal stability
  • the present invention provides a negative dielectric anisotropy liquid crystal composition, which comprises a liquid crystal compound represented by formula I and one or more liquid crystal compounds represented by formula II:
  • R 1 represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms
  • R 2 represents an alkyl group having 1 to 10 carbon atoms or one having 1 to 10 carbon atoms Alkoxy, alkenyl or alkenyloxy having 2-10 carbon atoms; wherein any one or more of the groups represented by R 1 and R 2 are unconnected -CH 2 -optionally substituted by ring Pentyl or cyclopropylene substitution.
  • the present disclosure also provides a liquid crystal display element comprising the liquid crystal composition of the present disclosure, and the liquid crystal display element is an active matrix addressing display element or a passive matrix addressing display element.
  • the present disclosure also provides a liquid crystal display including the liquid crystal composition of the present disclosure, and the liquid crystal display is an active matrix addressing display or a passive matrix addressing display.
  • the liquid crystal composition of the present invention has high optical anisotropy ( ⁇ n), low rotational viscosity ⁇ 1 / elastic constant K ratio, and high clearing point on the basis of maintaining suitable electrical anisotropy ( ⁇ ). (Cp), good thermal stability (VHR), can realize the fast response of liquid crystal display.
  • the display element or liquid crystal display containing the liquid crystal composition disclosed in the present invention can be used to develop a high-frequency liquid crystal display element or liquid crystal display with low cell thickness and rapid response.
  • the present invention provides a negative dielectric anisotropy liquid crystal composition, characterized in that the liquid crystal composition comprises a liquid crystal compound represented by formula I and one or more liquid crystal compounds represented by formula II:
  • R 1 represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms
  • R 2 represents an alkyl group having 1 to 10 carbon atoms, and one having 1 to 10 carbon atoms Alkoxy, alkenyl with 2 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms; wherein any one or more of the groups represented by R 1 and R 2 are unconnected -CH 2 -optionally substituted by cyclopentylene or cyclopropylidene.
  • the liquid crystal composition of the present invention has high optical anisotropy ( ⁇ n), low rotational viscosity ( ⁇ 1 ), high clearing point (Cp), Good low-temperature storage performance, good thermal stability (VHR), can realize the fast response of liquid crystal display.
  • the compound represented by formula II is selected from the group consisting of compounds represented by formula II-1 to formula II-6:
  • liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula III:
  • R 3 and R 4 each independently represent an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a fluorine-substituted Is an alkoxy group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms or a fluorine-substituted alkenyl group having 2-10 carbon atoms;
  • any one or more unconnected -CH 2 -in the groups represented by R 3 and R 4 is optionally substituted by cyclopentylene or cyclopropylidene;
  • X represents a single bond, -CH 2 CH 2 -or -CH 2 O-;
  • n 1 or 2;
  • the compound represented by the aforementioned formula III is selected from the group consisting of the compounds represented by the formula III-1 to the formula III-13:
  • R 3 and R 4 each independently represent an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a fluorine-substituted Is an alkoxy group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms or a fluorine-substituted alkenyl group having 2-10 carbon atoms;
  • any one or more unconnected -CH 2 -in the groups represented by R 3 and R 4 is optionally substituted by cyclopentylene or cyclopropylidene.
  • liquid crystal composition of the present disclosure preferably further contains one or more compounds represented by formula IV in addition to the compound represented by formula I:
  • R 5 and R 6 each independently represent an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a fluorine-substituted Is an alkoxy group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms or a fluorine-substituted alkenyl group having 2-10 carbon atoms;
  • n 1 or 2;
  • the aforementioned compound represented by formula IV other than the compound represented by formula I is selected from the group consisting of compounds represented by formula IV-1 to IV-5:
  • R 5 and R 6 each independently represent an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a fluorine-substituted The alkoxy group having 1-10 carbon atoms, the alkenyl group having 2-10 carbon atoms or the fluorine-substituted alkenyl group having 2-10 carbon atoms.
  • liquid crystal composition of the present disclosure preferably further contains one or more compounds represented by formula V:
  • R 7 and R 8 represent an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a fluorine-substituted carbon group.
  • Z represents O or S.
  • the compound represented by formula V is selected from the group consisting of compounds represented by formula V-1 to V-12:
  • R 71 and R 81 each independently represent an alkyl group having 1 to 10 carbon atoms.
  • Examples of the aforementioned alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, and isopentyl. Base, hexyl, heptyl, octyl, nonyl, decyl, etc.
  • Examples of the aforementioned alkoxy group having 1 to 10 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, and pentoxy. Group, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, etc.
  • Examples of the aforementioned alkenyl group having 2 to 10 carbon atoms include vinyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 1-pentenyl. , 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, etc.
  • fluorine-substituted alkyl groups with 1-10 carbon atoms fluorine-substituted alkoxy groups with 1-10 carbon atoms, fluorine-substituted alkenyl groups with 2-10 carbon atoms, and fluorine-substituted carbons
  • the "fluorine substitution" in the alkenyloxy group with 3-8 atoms can be mono-fluorine substitution, or polyfluorine substitution such as difluorine substitution, trifluorine substitution, or perfluorine substitution. There is no substitution for fluorine. Special restrictions.
  • fluorine-substituted alkyl groups with 1-10 carbon atoms fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1 ,2-Difluoroethyl, 1,1-difluoroethyl, 1,1,2-trifluoroethyl, 1,1,1,2,2-pentafluoro-substituted ethyl, etc. but not limited thereto.
  • the liquid crystal composition contains according to mass percentage:
  • the mass percentage of the compound represented by formula I is 1-12%, and more preferably the mass percentage of the compound represented by formula I is 1-10%;
  • the mass percentage of the compound represented by formula II is 5-25%, and more preferably the mass percentage of the compound represented by formula II is 5-20%;
  • the mass percentage of the compound represented by formula III is 25-65%, and more preferably the mass percentage of the compound represented by formula III is 25-56%;
  • the mass percentage of the compound represented by formula IV is 15-65%, and more preferably the mass percentage of the compound represented by formula IV is 15-55%;
  • the mass percentage of the compound represented by formula V is 1-10%, and more preferably the mass percentage of the compound represented by formula V is 1-8%;
  • various functional dopants can be added.
  • the content of the dopant is preferably 0.01% by mass in the liquid crystal composition. ⁇ 1.5%, these dopants include, for example, antioxidants, ultraviolet absorbers, and chiral agents.
  • Antioxidants can be listed,
  • t represents an integer of 1-10;
  • R 0 represents an alkyl group having 1 to 10 carbon atoms
  • Z 0 represents an alkylene group having a carbon number of 1-20, any one or more hydrogen in the alkylene group is optionally substituted by halogen, and any one or more -CH 2 -is optionally -O -replace;
  • UV absorbers can be listed,
  • R 01 represents an alkyl group having 1 to 10 carbon atoms.
  • the present invention also relates to a liquid crystal display element or liquid crystal display comprising any one of the above-mentioned liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
  • the liquid crystal display element or liquid crystal display of the present invention is preferably an active matrix addressing liquid crystal display element or liquid crystal display.
  • the aforementioned active matrix display element or display specifically includes, for example, TN-TFT or IPS-TFT or FFS-TFT or UV2A-TFT liquid crystal display element or other TFT displays.
  • the liquid crystal display element or liquid crystal display of the present invention includes the liquid crystal composition disclosed in the present invention.
  • the liquid crystal display element or the liquid crystal display of the present invention has a higher optical anisotropy ⁇ n and a faster response speed, and is mainly applied to a high-frequency liquid crystal display element or a liquid crystal display with a low cell thickness and a fast response.
  • the preparation methods are conventional methods unless otherwise specified.
  • the raw materials used can be obtained from publicly disclosed commercial sources unless otherwise specified.
  • the specific meanings and test conditions of the liquid crystal monomer and other symbols are as follows:
  • Cp represents the clearing point of liquid crystal (°C), measured by DSC quantitative method
  • the test condition is 25 ⁇ 0.5°C, 20 micron parallel box, INSTEC: ALCT-IR1 test;
  • ⁇ 1 means rotational viscosity (mPa ⁇ s), the test condition is 25 ⁇ 0.5°C, 20 micron vertical box, INSTEC:ALCT-IR1 test;
  • K 11 is the splay elastic constant
  • K 33 is the flexural elastic constant
  • the test conditions are: 25 ⁇ 2°C
  • INSTEC ALCT-IR1, 20 micron vertical box;
  • VHR represents the voltage retention rate (%)
  • the test conditions are 20 ⁇ 2°C
  • the voltage is ⁇ 5V
  • the pulse width is 10ms
  • the voltage retention time is 16.7ms.
  • the test equipment is TOYO Model6254 LCD performance comprehensive tester;
  • GTG represents the time required to switch between different gray scales of the liquid crystal display device.
  • the test condition is 25 ⁇ 1°C
  • the test voltage is the corresponding voltage of the corresponding gray scale
  • the test frequency is 64 Hz.
  • the test equipment is DMS505.
  • the preparation method of the liquid crystal composition is as follows: each liquid crystal monomer is weighed according to a certain ratio and put into a stainless steel beaker, the stainless steel beaker containing each liquid crystal monomer is placed on a magnetic stirring instrument and heated and melted. After most of the liquid crystal monomer is melted, a magnetic rotor is added to the stainless steel beaker, the mixture is stirred uniformly, and the liquid crystal composition is obtained after cooling to room temperature.
  • the structure of the liquid crystal monomer in the embodiment of the present invention is represented by a code, and the code representation method of the liquid crystal ring structure, terminal group, and connecting group is shown in Table 1 and Table 2 below.
  • VHR Voltage Holding Ratio
  • VHR Voltage Holding Ratio
  • the experiment is to pour the liquid crystals of the example and the comparative example into a test box for testing, and the test condition is 60 ⁇ 1°C, voltage of ⁇ 5V, pulse width of 10ms, voltage holding time of 166.7ms (the voltage holding time and frequency are the reciprocal relationship between each other, and the conversion frequency is 6Hz); the test equipment is TOYO Model 6254 LCD performance comprehensive tester; VHR initial The value is the data obtained by testing the test box without any treatment.
  • the VHR high temperature is the VHR value obtained by testing the test box filled with liquid crystal in a high-temperature oven at 100°C for 1 hour.
  • liquid crystal composition of the present invention has strong resistance to high temperature aging, so that it has a strong ability to resist damage to the external environment during operation, has higher reliability, and can be better used for high temperature and high backlight liquid crystal displays Component or liquid crystal display.
  • GTG represents the time required to switch between different gray scales of the liquid crystal display device.
  • the experiment is to pour the liquid crystals of the embodiment and the comparative example into the test box and test in the DMS505.
  • the test condition is 25 ⁇ 1°C
  • the test voltage is the corresponding gray.
  • the corresponding voltage and test frequency are 64Hz.
  • the smaller the value of GTG the faster the response speed of the liquid crystal composition in the liquid crystal display element or display.
  • the ⁇ 1 /K 11 of the liquid crystal composition has a decisive effect on the response speed of the liquid crystal display element or the display.
  • the liquid crystal of the present invention is used.
  • the composition has a smaller ⁇ 1 /K 11 , so that it can be better applied to high-frequency and fast-response liquid crystal display elements or displays.
  • liquid crystal composition of the present invention has higher optical anisotropy ( ⁇ n) and lower rotational viscosity ( ⁇ 1 ) on the basis of maintaining suitable electrical anisotropy ( ⁇ ).
  • ⁇ n optical anisotropy
  • ⁇ 1 rotational viscosity
  • High clearing point (Cp) good thermal stability (VHR)
  • VHR thermal stability
  • the display element or liquid crystal display containing the liquid crystal composition disclosed in the present invention can be used to develop a high-frequency liquid crystal display element or liquid crystal display with low cell thickness and rapid response.

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Abstract

本发明属于液晶材料技术领域，具体涉及一种负介电各向异性的液晶组合物及含有该液晶组合物的液晶显示元件或液晶显示器。本发明公开了一种负介电各向异性的液晶组合物，该液晶组合物包含式Ⅰ所示的液晶化合物以及一种或多种式Ⅱ所示的化合物。本发明的液晶组合物具有高的光学各向异性、高的清亮点和良好的热稳定性，包含本发明液晶组合物的液晶显示元件和液晶显示器具有较快的响应速度。

Description

液晶组合物、液晶显示元件、液晶显示器 技术领域
本发明属于液晶显示领域，更具体地，涉及一种负介电各向异性的液晶组合物及包含该液晶组合物的液晶显示元件、液晶显示器。
背景技术
液晶显示元件根据显示方式分为下列模式：扭曲向列相(TN)模式、超扭曲向列相(STN)模式、平面转换模式(IPS)或边缘场控制模式(FFS)、垂直配向(VA)模式。无论何种显示模式均需要液晶组合物具合适的光学各向异性△n、合适的介电各向异性△ε、低旋转粘度γ 1、光和热的稳定性以及良好的低温存储性能。
随着科学技术的高速发展，显示行业也在不断的向前进步，由此对液晶显示元件或显示器的要求也越来越高。越来越多的显示应用要求具有更快的响应速度和更高的可靠性。对于显示器件所用的液晶材料，要求具有①快速响应：具有较高的光学各向异性△n，以此来匹配更低的盒厚来达到相同的延迟量△nd设计；具有较低的旋转粘度γ 1和较高的弹性系数K；②高可靠性：高的电荷保持率，高的比电阻值，优良的耐高温稳定性及对UV光或背光的抗老化性能。而实际研究中发现，液晶组合物同时兼具快速响应和高可靠性会非常困难。因此，开发兼具快速响应和良好高温稳定性的液晶组合物是亟待解决的问题。
发明内容
为了解决上述技术问题，本发明提供的液晶组合物在维持合适的电学各向异性(Δε)的基础上具有较高的光学各向异性(Δn)、较低的旋转粘度γ 1/弹性常数K的比值、高的清亮点(Cp)、良好的热稳定性(VHR)。
为达到上述目的，本发明采用下述技术方案：
本发明提供一种负介电各向异性液晶组合物，该液晶组合物包含式Ⅰ所示的液晶化合物以及一种或多种式Ⅱ所示的液晶化合物：
Figure PCTCN2020110963-appb-000001
其中，R 1表示碳原子数为1～10的烷基或碳原子数为1～10的烷氧基；R 2表示碳原子数为1～10的烷基或碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或链烯氧基；其中 R 1、R 2所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代。
本公开还提供液晶显示元件，其包含本公开的液晶组合物，所述液晶显示元件为有源矩阵寻址显示元件或者无源矩阵寻址显示元件。
本公开还提供液晶显示器，其包含本公开的液晶组合物，所述液晶显示器为有源矩阵寻址显示器或者无源矩阵寻址显示器。
发明效果
本发明的液晶组合物在维持合适的电学各向异性(Δε)的基础上具有较高的光学各向异性(Δn)、较低的旋转粘度γ 1/弹性常数K的比值、高的清亮点(Cp)、良好的热稳定性(VHR)，可以实现液晶显示的快速响应。且包含本发明公开的液晶组合物显示元件或液晶显示器，可以用于开发低盒厚快速响应的高频率液晶显示元件或液晶显示器。
具体实施方式
[液晶组合物]
本发明提供一种负介电各向异性液晶组合物，其特征在于，所述液晶组合物包含式Ⅰ所示的液晶化合物以及一种或多种式Ⅱ所示的液晶化合物：
Figure PCTCN2020110963-appb-000002
其中，R 1表示碳原子数为1～10的烷基或碳原子数为1～10的烷氧基；R 2表示碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或碳原子数为2～10的链烯氧基；其中R 1、R 2所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代。
本发明的液晶组合物在维持合适的电学各向异性(Δε)的基础上具有较高的光学各向异性(Δn)、较低的旋转粘度(γ 1)、高的清亮点(Cp)、良好的低温存储性能、良好的热稳定性(VHR)，可以实现液晶显示的快速响应。
本发明的液晶组合物中，优选地，前述式Ⅱ所示化合物选自式Ⅱ-1至式Ⅱ-6所示化合物组成的组：
Figure PCTCN2020110963-appb-000003
Figure PCTCN2020110963-appb-000004
本发明的液晶组合物，优选地，还包含一种或多种式Ⅲ所示化合物：
Figure PCTCN2020110963-appb-000005
其中，R 3、R 4各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
其中R 3、R 4所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代；
X表示单键、-CH 2CH 2-或-CH 2O-；
m表示1或2；
当m表示1时，
Figure PCTCN2020110963-appb-000006
表示
Figure PCTCN2020110963-appb-000007
当m表示2时，两个
Figure PCTCN2020110963-appb-000008
各自独立地表示
Figure PCTCN2020110963-appb-000009
即当m表示2时，两个
Figure PCTCN2020110963-appb-000010
可以组合表示
Figure PCTCN2020110963-appb-000011
Figure PCTCN2020110963-appb-000012
等
本发明的液晶组合物中，优选地，前述式Ⅲ所示化合物选自式Ⅲ-1至式Ⅲ-13所示化 合物组成的组：
Figure PCTCN2020110963-appb-000013
Figure PCTCN2020110963-appb-000014
其中，R 3、R 4各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
其中R 3、R 4所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代。
本公开的液晶组合物中，优选地，还包含一种或多种除式Ⅰ所示化合物之外的式Ⅳ所示化合物：
Figure PCTCN2020110963-appb-000015
其中，R 5、R 6各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
n表示1或2；
Figure PCTCN2020110963-appb-000016
各自独立地表示
Figure PCTCN2020110963-appb-000017
当n表示2时，两个
Figure PCTCN2020110963-appb-000018
各自独立地表示
Figure PCTCN2020110963-appb-000019
即当n表示2时，两个
Figure PCTCN2020110963-appb-000020
可以组合表示
Figure PCTCN2020110963-appb-000021
Figure PCTCN2020110963-appb-000022
本发明的液晶组合物中，优选地，前述除式Ⅰ所示化合物之外的式Ⅳ所示化合物选自式式Ⅳ-1至Ⅳ-5所示化合物组成的组：
Figure PCTCN2020110963-appb-000023
其中，R 5、R 6各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基。
本公开的液晶组合物中，优选地，还包含一种或多种式Ⅴ所示的化合物：
Figure PCTCN2020110963-appb-000024
其中，R 7、R 8表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、或者氟取代的碳原子数为1～10的烷氧基，其中R 7中任意一个或多个不相连的-CH 2-任选被亚环戊基、亚环丁基或亚环丙基取代；
Z表示O或S。
本发明的液晶组合物中，优选地，前述式Ⅴ所示化合物选自式式Ⅴ-1至Ⅴ-12所示化合物组成的组：
Figure PCTCN2020110963-appb-000025
Figure PCTCN2020110963-appb-000026
其中，R 71、R 81各自独立地表示碳原子数为1～10的烷基。
作为前述碳原子数为1～10的烷基，可以列举出例如，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、己基、庚基、辛基、壬基、癸基等。
作为前述的碳原子数为1～10的烷氧基，可以列举出例如，甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基等。
作为前述碳原子数为2～10的链烯基，可以列举出例如，乙烯基、1-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-己烯基、2-己烯基、3-己烯基等。
前述的氟取代的碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷氧基、氟取代的碳原子数为2-10的链烯基、氟取代的碳原子数为3-8的链烯氧基中的“氟取代”可以是单氟取代，或者、二氟取代、三氟取代等多氟取代，也可以是全氟取代，对氟的取代数没有特别的限定。例如，作为氟取代的碳原子数为1-10的烷基，可以列举出氟代甲基、二氟甲基、三氟甲基、1-氟代乙基、2-氟代乙基、1,2-二氟乙基、1,1-二氟乙基、1,1,2-三氟乙基、1,1,1,2,2-五氟取代乙基等但不限于此。
优选地，所述液晶组合物按照质量百分数包含：
优选地式Ⅰ所示化合物的质量百分含量为1～12％，进一步优选地式Ⅰ所示化合物的质量百分含量为1～10％；
优选地式Ⅱ所示化合物的质量百分含量为5～25％，进一步优选地式Ⅱ所示化合物的质 量百分含量为5～20％；
优选地式Ⅲ所示化合物的质量百分含量为25～65％，进一步优选地式Ⅲ所示化合物的质量百分含量为25～56％；
优选地式Ⅳ所示化合物的质量百分含量为15～65％，进一步优选地式Ⅳ所示化合物的质量百分含量为15～55％；
优选地式Ⅴ所示化合物的质量百分含量为1～10％，进一步优选地式Ⅴ所示化合物的质量百分含量为1～8％；
本发明的液晶组合物中，可选的，还可以加入各种功能的掺杂剂，在含有掺杂剂的情况下，掺杂剂的含量优选在液晶组合物中所占的质量百分比为0.01～1.5％，这些掺杂剂可以列举出例如抗氧化剂、紫外线吸收剂、手性剂。
抗氧化剂可以列举出，
Figure PCTCN2020110963-appb-000027
其中，t表示1～10的整数；
手性剂可以列举出，
Figure PCTCN2020110963-appb-000028
其中，R 0表示碳原子数为1～10的烷基；
光稳定剂可以列举出，
Figure PCTCN2020110963-appb-000029
其中，Z 0表示碳数为1～20的亚烷基，所述亚烷基中任意的一个或多个氢任选被卤素取 代，任意的一个或多个-CH 2-任选被-O-取代；
紫外线吸收剂可以列举出，
Figure PCTCN2020110963-appb-000030
其中，R 01表示碳原子数为1～10的烷基。
[液晶显示元件或液晶显示器]
本发明还涉及包含上述任意一种液晶组合物的液晶显示元件或液晶显示器；所述显示元件或显示器为有源矩阵显示元件或显示器或无源矩阵显示元件或显示器。
本发明的液晶显示元件或液晶显示器优选有源矩阵寻址液晶显示元件或液晶显示器。
前述有源矩阵显示元件或显示器具体可以列举出例如TN-TFT或IPS-TFT或FFS-TFT或UV2A-TFT液晶显示元件或其他TFT显示器。
本发明的液晶显示元件或液晶显示器包含本发明公开的液晶组合物。本发明的液晶显示元件或液晶显示器具有较高的光学各向异性Δn以及较快的响应速度，主要应用于低盒厚快速响应的高频率液晶显示元件或液晶显示器。
实施例
为了更清楚地说明本发明，下面结合优选实施例对本发明做进一步的说明。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本发明的保护范围。
本发明中，制备方法如无特殊说明则均为常规方法，所用的原料如无特别说明均可从公开的商业途径获得，百分比均是指质量百分比，温度为摄氏度(℃)，液晶化合物也成为液晶单体，其他符号的具体意义及测试条件如下：
Cp表示液晶清亮点(℃)，DSC定量法测试；
Δn表示光学各向异性，Δn＝n e-n o，其中，n o为寻常光的折射率，n e为非寻常光的折射率，测试条件为25±2℃，589nm，阿贝折射仪测试；
Δε表示介电各向异性，Δε＝ε ∥-ε ⊥，其中，ε ∥为平行于分子轴的介电常数，ε ⊥为垂直于分子轴的介电常数，测试条件为25±0.5℃，20微米平行盒，INSTEC:ALCT-IR1测试；
γ 1表示旋转粘度(mPa·s),测试条件为25±0.5℃，20微米垂直盒，INSTEC:ALCT-IR1 测试；
K 11为展曲弹性常数，K 33为弯曲弹性常数，测试条件为：25±2℃、INSTEC:ALCT-IR1、20微米垂直盒；
VHR表示电压保持率(％)，测试条件为20±2℃、电压为±5V、脉冲宽度为10ms、电压保持时间16.7ms。测试设备为TOYO Model6254液晶性能综合测试仪；
GTG表示液晶显示器件不同灰阶之间切换所需要的时间，测试条件25±1℃、测试电压为相应灰阶对应电压、测试频率为64Hz。测试设备为DMS505。
液晶组合物的制备方法如下：将各液晶单体按照一定配比称量后放入不锈钢烧杯中，将装有各液晶单体的不锈钢烧杯置于磁力搅拌仪器上加热融化，待不锈钢烧杯中的液晶单体大部份融化后，往不锈钢烧杯中加入磁力转子，将混合物搅拌均匀，冷却到室温后即得液晶组合物。
本发明实施例液晶单体结构用代码表示，液晶环结构、端基、连接基团的代码表示方法见下表1、表2。
表1环结构的对应代码
Figure PCTCN2020110963-appb-000031
Figure PCTCN2020110963-appb-000032
表2端基与链接基团的对应代码
Figure PCTCN2020110963-appb-000033
Figure PCTCN2020110963-appb-000034
举例：
Figure PCTCN2020110963-appb-000035
其代码为CC-Cp-V1；
Figure PCTCN2020110963-appb-000036
其代码为PGP-Cpr1-2；
Figure PCTCN2020110963-appb-000037
其代码为CPY-2-O2；
Figure PCTCN2020110963-appb-000038
其代码为CCY-3-O2；
Figure PCTCN2020110963-appb-000039
其代码为COY-3-O2；
Figure PCTCN2020110963-appb-000040
其代码为CCOY-3-O2；
Figure PCTCN2020110963-appb-000041
其代码为Sb-CpO-O4；
Figure PCTCN2020110963-appb-000042
其代码为Sc-CpO-O4。
实施例1
液晶组合物的配方及相应的性能如下表3所示。
表3实施例1液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000043
实施例2
液晶组合物的配方及相应的性能如下表4所示。
表4实施例2液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000044
Figure PCTCN2020110963-appb-000045
实施例3
液晶组合物的配方及相应的性能如下表5所示。
表5实施例3液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000046
Figure PCTCN2020110963-appb-000047
实施例4
液晶组合物的配方及相应的性能如下表6所示。
表6实施例4液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000048
Figure PCTCN2020110963-appb-000049
对比例1
液晶组合物的配方及相应的性能如下表7所示。
表7对比例1液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000050
Figure PCTCN2020110963-appb-000051
对比例2
液晶组合物的配方及相应的性能如下表8所示。
表8对比例2液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000052
Figure PCTCN2020110963-appb-000053
对比例3
液晶组合物的配方及相应的性能如下表9所示。
表9对比例3液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000054
对比例4
液晶组合物的配方及相应的性能如下表10所示。
表10对比例4液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000055
表11实施例1～4与对比例1～3的VHR对照值
Figure PCTCN2020110963-appb-000056
Figure PCTCN2020110963-appb-000057
VHR(Voltage Holding Ratio)表示液晶组合物在施加外电压情况下的液晶分子的电压保持率(％)，实验是将实施例和对比例的液晶分别灌注到测试盒中进行测试，测试条件为60±1℃、电压为±5V、脉冲宽度为10ms、电压保持时间166.7ms(电压保持时间与频率互为倒数关系，换算频率为6Hz)；测试设备为TOYO Model 6254液晶性能综合测试仪；VHR初始值为对不经过任何处理的测试盒进行测试获得的数据，VHR高温是把灌注好液晶的测试盒在高温烘箱100℃中放置1小时后进行测试得到的VHR值。液晶组合物的高温老化前后VHR差值(高温VHR减初始VHR)越大，表示液晶的抗高温性能越好。因此，本发明的液晶组合物具有良好抗高温老化的能力。
以上对比实验充分的说明本发明的液晶组合物的抗高温老化的能力强，从而在工作过程中抵抗外界环境破坏的能力强，信赖性更高，可以更好的用于高温高背光的液晶显示元件或液晶显示器。
表12实施例1～4与对比例3、4的γ 1/K 11和GTG响应对照值
Figure PCTCN2020110963-appb-000058
GTG表示液晶显示器件不同灰阶之间切换所需要的时间，实验是将实施例和对比例的液晶分别灌注到测试盒中在DMS505进行测试，测试条件为25±1℃、测试电压为相应灰阶对应电压、测试频率为64Hz。GTG的数值越小，表示液晶组合物在液晶显示元件或显示器中的响应速度越快。
以上实施例和对比例中随着589nm波长下的折射率Δn的增加，其相对应的盒厚设计也越薄，那么其对应的GTG响应速度也会越快。对比例3、4与实施例1、4相比，当盒厚设计相同时，液晶组合物的γ 1/K 11对液晶显示元件或显示器的响应速度的影响起决定性 作用，使用本发明的液晶组合物具有更小的γ 1/K 11，从而可以更好的应用到高频率快速响应的液晶显示元件或显示器。
实施例5
液晶组合物的配方及相应的性能如下表13所示。
表13实施例5液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000059
实施例6
液晶组合物的配方及相应的性能如下表14所示。
表14实施例6液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000060
实施例7
液晶组合物的配方及相应的性能如下表15所示。
表15实施例7液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000061
Figure PCTCN2020110963-appb-000062
实施例8
液晶组合物的配方及相应的性能如下表16所示。
表16实施例8液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000063
Figure PCTCN2020110963-appb-000064
实施例9
液晶组合物的配方及相应的性能如下表17所示。
表17实施例9液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000065
Figure PCTCN2020110963-appb-000066
实施例10
液晶组合物的配方及相应的性能如下表18所示。
表18实施例9液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000067
Figure PCTCN2020110963-appb-000068
实施例11
液晶组合物的配方及相应的性能如下表19所示。
表19实施例11液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000069
Figure PCTCN2020110963-appb-000070
实施例12
液晶组合物的配方及相应的性能如下表20所示。
表20实施例12液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000071
Figure PCTCN2020110963-appb-000072
实施例13
液晶组合物的配方及相应的性能如下表21所示。
表21实施例13液晶组合物的配方及相应的性能
Figure PCTCN2020110963-appb-000073
Figure PCTCN2020110963-appb-000074
由以上列举的所有实施例表明，本发明的液晶组合物在维持合适的电学各向异性(Δε)的基础上具有较高的光学各向异性(Δn)、较低的旋转粘度(γ 1)、高的清亮点(Cp)、良好的热稳定性(VHR)，可以实现液晶显示的快速响应。且包含本发明公开的液晶组合物显示元件或液晶显示器，可以用于开发低盒厚快速响应的高频率液晶显示元件或液晶显示器。
本发明的上述实施例仅仅是为清楚地说明本发明所作的举例，而并非是对本发明的实施方式的限定，对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动，这里无法对所有的实施方式予以穷举，凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。

Claims (9)

  1. 一种负介电各向异性液晶组合物，其特征在于，所述液晶组合物包含式Ⅰ所示的液晶化合物以及一种或多种式Ⅱ所示的液晶化合物：
    Figure PCTCN2020110963-appb-100001
    其中，
    R 1表示碳原子数为1～10的烷基或碳原子数为1～10的烷氧基；R 2表示碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或碳原子数为2～10的链烯氧基；其中R 1、R 2所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代。
  2. 根据权利要求1所述的液晶组合物，其特征在于，所述液晶组合物还包含一种或多种式Ⅲ所示的化合物：
    Figure PCTCN2020110963-appb-100002
    其中，
    R 3、R 4各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
    其中R 3、R 4所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代；
    X表示单键、-CH 2CH 2-或-CH 2O-；
    m表示1或2；
    当m表示1时，
    Figure PCTCN2020110963-appb-100003
    表示
    Figure PCTCN2020110963-appb-100004
    当m表示2时，两个
    Figure PCTCN2020110963-appb-100005
    各自独立地表示
    Figure PCTCN2020110963-appb-100006
  3. 根据权利要求2所述的液晶组合物，其特征在于，所述式Ⅲ所示的化合物选自式Ⅲ-1至Ⅲ-13所示化合物组成的组：
    Figure PCTCN2020110963-appb-100007
    其中，
    R 3、R 4各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
    其中，R 3、R 4所示基团中任意一个或多个不相连的-CH 2-任选的被亚环戊基或亚环丙基取代。
  4. 根据权利要求2所述的液晶组合物，其特征在于，所述液晶组合物还包含除式Ⅰ所示化合物以外的一种或多种式Ⅳ所示的化合物：
    Figure PCTCN2020110963-appb-100008
    其中，
    R 5、R 6各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯基或氟取代的碳原子数为2～10的链烯基；
    n表示1或2；
    Figure PCTCN2020110963-appb-100009
    各自独立地表示
    Figure PCTCN2020110963-appb-100010
    当n表示2时，两个
    Figure PCTCN2020110963-appb-100011
    各自独立地表示
    Figure PCTCN2020110963-appb-100012
  5. 根据权利要求4所述的液晶组合物，其特征在于，所述除式Ⅰ所示化合物之外的式Ⅳ所示的化合物选自式Ⅳ-1至Ⅳ-5所示化合物组成的组：
    Figure PCTCN2020110963-appb-100013
    其中，
    R 5、R 6各自独立地表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、氟取代的碳原子数为1～10的烷氧基、碳原子数为2～10的链烯 基或氟取代的碳原子数为2～10的链烯基。
  6. 根据权利要求4所述的液晶组合物，其特征在于，所述液晶组合物还包含一种或多种式Ⅴ所示化合物：
    Figure PCTCN2020110963-appb-100014
    其中，R 7、R 8表示碳原子数为1～10的烷基、氟取代的碳原子数为1～10的烷基、碳原子数为1～10的烷氧基、或者氟取代的碳原子数为1～10的烷氧基，其中R 7中任意一个或多个不相连的-CH 2-任选被亚环戊基、亚环丁基或亚环丙基取代；
    Z表示O或S。
  7. 根据权利要求6所述的液晶组合物，其特征在于，所述式Ⅴ所示的化合物选自下述式Ⅴ-1至Ⅴ-12所示的化合物组成的组：
    Figure PCTCN2020110963-appb-100015
    Figure PCTCN2020110963-appb-100016
    其中，R 71、R 81各自独立地表示碳原子数为1～10的烷基。
  8. 一种液晶显示元件，其特征在于，包含权利要求1～7的任一项所述的液晶组合物，所述液晶显示元件为有源矩阵寻址显示元件，或者无源矩阵寻址显示元件。
  9. 一种液晶显示器，其特征在于，包含权利要求1～7的任一项所述的液晶组合物，所述液晶显示器为有源矩阵寻址显示器，或者无源矩阵寻址显示器。
PCT/CN2020/110963 2020-06-16 2020-08-25 液晶组合物、液晶显示元件、液晶显示器 WO2021253621A1 (zh)

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