WO2018192476A1 - 一种液晶组合物及其显示器件 - Google Patents

一种液晶组合物及其显示器件 Download PDF

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WO2018192476A1
WO2018192476A1 PCT/CN2018/083330 CN2018083330W WO2018192476A1 WO 2018192476 A1 WO2018192476 A1 WO 2018192476A1 CN 2018083330 W CN2018083330 W CN 2018083330W WO 2018192476 A1 WO2018192476 A1 WO 2018192476A1
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liquid crystal
crystal composition
group
formula
carbon atoms
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PCT/CN2018/083330
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English (en)
French (fr)
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韩文明
徐海彬
徐爽
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江苏和成显示科技有限公司
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Priority to JP2019555642A priority Critical patent/JP6940049B2/ja
Priority to KR1020197022954A priority patent/KR102223661B1/ko
Priority to US16/483,933 priority patent/US11155752B2/en
Publication of WO2018192476A1 publication Critical patent/WO2018192476A1/zh

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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K19/126—Compounds containing at least one asymmetric carbon atom
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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    • 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
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3009—Cy-Ph
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
    • 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
    • G02F1/0009—Materials therefor
    • G02F1/0045—Liquid crystals characterised by their physical properties
    • 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
    • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
    • G02F1/13712—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy

Definitions

  • the present invention relates to the field of liquid crystal materials, and in particular to a liquid crystal composition having negative dielectric anisotropy and a display device thereof.
  • the liquid crystal display element can be used in various household electric appliances, measurement equipment, automobile panels, word processors, computers, printers, televisions, and the like represented by watches and clocks and electronic calculators.
  • the type of display mode it is divided into PC (phase change), TN (twist nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment).
  • PM passive matrix
  • AM active matrix
  • PM is divided into static (static) and multiplex (multiplex) types.
  • the AM is classified into a TFT (thin film transistor), a MIM (metal insulator metal), and the like.
  • the types of TFTs are amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to a manufacturing process.
  • the liquid crystal display element is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmissive type using both natural light and backlight depending on the type of the light source.
  • the IPS mode, the ECB mode, the VA mode, or the CSH mode differ from the conventional TN mode or the STN mode in that the former uses a liquid crystal material having a negative dielectric anisotropy.
  • the VA mode has a very dark contrast ratio compared to the conventional TN mode, and the contrast is less dependent on the birefringence of the liquid crystal, the thickness of the liquid crystal layer, and the wavelength of the incident light, and the VA mode is The wide viewing angle also has a good performance.
  • the VA mode can also omit the rubbing process, resulting in an increase in yield.
  • the liquid crystal composition is often required to have a large negative value of negative dielectric anisotropy, and also requires a higher clearing point, a lower threshold voltage, and a faster response time, in addition to Has good low temperature stability.
  • liquid crystal composition which has large optical anisotropy, large absolute value of negative dielectric anisotropy, good low temperature stability, and fast response.
  • a liquid crystal composition having a large absolute value of dielectric anisotropy has a high critical voltage, high power consumption, and a relatively slow response speed. Therefore, in order to meet the increasing demand for applications, there is a need in the art for liquid crystal compounds that continuously improve negative dielectric anisotropy.
  • an object of the present invention is to provide a liquid crystal composition having large optical anisotropy, large absolute value of negative dielectric anisotropy, low temperature stability, and rapid response. Its display device.
  • a liquid crystal composition comprising:
  • R 1 and R 2 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • R 2 represents an alkoxy group having 1 to 12 carbon atoms or an alkenyloxy group having 2 to 12 carbon atoms, and the alkane having 1 to 12 carbon atoms
  • One or more non-adjacent -CH 2 - of the oxy group or the alkenyloxy group having 2 to 12 carbon atoms may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the liquid crystal composition comprises at least two compounds of the formula I, and the compound of the formula I accounts for 1-35 wt% of the total weight of the liquid crystal composition. .
  • the compound of Formula I is selected from the group consisting of:
  • R 3 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms
  • n an integer of 2-6.
  • At least two of the compounds of formula I are selected from the group consisting of:
  • At least one compound of the formula I is selected from the group consisting of the compounds I-a-1 to I-a-4, I-b-1 to I-b-4 and I-c.
  • the liquid crystal composition comprises at least two compounds of the formula I, and the compound of the formula I accounts for 5-30% by weight of the total weight of the liquid crystal composition. .
  • the compound of Formula I is selected from the group consisting of:
  • R 3 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms
  • n an integer of 2-6;
  • the compound of the formula I accounts for from 1 to 35 wt% of the total weight of the liquid crystal composition.
  • the compound of Formula I is selected from the group consisting of:
  • R 3 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms
  • n an integer of 2-6;
  • the compound of the formula I accounts for 5 to 30% by weight based on the total weight of the liquid crystal composition.
  • R 4 and R 5 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected;
  • ring Express Said One or more of -CH 2 - may be replaced by -O-
  • One or more H's may be replaced by F;
  • Z 1 represents a single bond, -CH 2 O-, -CF 2 O- or -COO-;
  • n 0 or 1.
  • R 41 and R 51 each independently represent an alkyl group or alkoxy group having 1 to 7 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 7 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the compound of the formula II-1 is selected from the group consisting of:
  • the compound of formula II-2 is selected from the group consisting of:
  • the compound of formula II-3 is selected from the group consisting of:
  • the compound of formula II-4 is selected from the group consisting of:
  • the compound of formula II-5 is selected from the group consisting of:
  • the compound of formula II-6 is selected from the group consisting of:
  • At least one compound of Formula III is further included
  • R 6 and R 7 each independently represent an alkyl or alkoxy group having 1 to 12 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 12 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected;
  • Z 2 represents a single bond, -CH 2 O-, -CF 2 O- or -COO-;
  • p 0 or 1.
  • R 61 and R 71 each independently represent an alkyl or alkoxy group having 1 to 7 carbon atoms or an alkenyl group or alkenyloxy group having 2 to 7 carbon atoms, wherein the alkyl group or alkoxy group One or more non-adjacent -CH 2 - in the alkenyl or alkenyloxy group may be independently replaced by -O- in such a manner that the oxygen atoms are not directly connected.
  • the compound of formula III-1 is selected from the group consisting of:
  • the compound of formula III-2 is selected from the group consisting of:
  • the compound of formula III-3 is selected from the group consisting of:
  • the compound of formula III-4 is selected from the group consisting of:
  • a liquid crystal display device comprising the above liquid crystal composition.
  • liquid crystal composition further comprises one or more additives known to those skilled in the art and described in the literature.
  • Stabilizers which can be added, for example, to the mixture according to the invention are mentioned below.
  • the stabilizer accounts for 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1 wt% of the total weight of the liquid crystal composition. As a particularly preferred embodiment, the stabilizer accounts for 0.01 to 0.1% by weight based on the total weight of the liquid crystal composition.
  • Another aspect of the present invention also provides a liquid crystal display comprising the liquid crystal composition provided by the present invention.
  • the liquid crystal composition provided by the invention has the characteristics of high absolute value of negative dielectric anisotropy, high optical anisotropy, good low temperature stability and fast response speed, and liquid crystal comprising the liquid crystal composition of the invention.
  • the display can meet the needs of low voltage drive and fast response.
  • the ratios are all by weight, and all temperatures are in degrees Celsius.
  • nCCGF The structural formula is expressed by the code listed in Table 1, and can be expressed as: nCCGF, where n in the code represents the number of C atoms of the left-end alkyl group, for example, n is "3", that is, the alkyl group is -C 3 H 7 ; C in the code represents a cyclohexane group, G represents 2-fluoro-1,4-phenylene, and F represents fluorine.
  • Optical anisotropy was measured using an Abbe refractometer under a sodium light (589 nm) light source at 25 °C.
  • ⁇ ⁇ ⁇ - ⁇ ⁇ , where ⁇ ⁇ is the dielectric constant parallel to the molecular axis, ⁇ ⁇ is the dielectric constant perpendicular to the molecular axis, test conditions: 25 ° C, 1 KHz, test box is TN90 type, box thickness 7 ⁇ m.
  • ⁇ 1 was tested using a TOYO6254 liquid crystal physical property evaluation system; the test temperature was 25 ° C, and the test voltage was 90V.
  • the components used in the following examples can be synthesized by a known method or obtained commercially. These synthetic techniques are conventional, and each of the obtained liquid crystal compounds has been tested to meet the standards of electronic compounds.
  • a liquid crystal composition was prepared in accordance with the ratio of each liquid crystal composition specified in the following examples.
  • the preparation of the liquid crystal composition is carried out according to a conventional method in the art, such as heating, ultrasonic wave, suspension, etc., in a predetermined ratio.
  • liquid crystal composition given in the following examples was prepared and studied.
  • the composition of each liquid crystal composition and the test results of its performance parameters are shown below.
  • the liquid crystal compositions of Comparative Example 1 were prepared according to the respective compounds and weight percentages listed in Table 2, and were filled in the performance test between the two substrates of the liquid crystal display.
  • the test data are shown in the following table:
  • Example 1 The liquid crystal composition of Example 1 was prepared according to each compound and weight percentage listed in Table 3, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is as shown in the following table:
  • Example 2 The liquid crystal composition of Example 2 was prepared according to each compound and weight percentage listed in Table 4, and was filled in the performance test between the two substrates of the liquid crystal display. The test data are shown in the following table:
  • Example 3 The liquid crystal composition of Example 3 was prepared according to each compound and weight percentage listed in Table 5, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is shown in the following table:
  • Example 4 The liquid crystal composition of Example 4 was prepared according to each compound and weight percentage listed in Table 6, and was filled in the performance test between the two substrates of the liquid crystal display. The test data are shown in the following table:
  • Example 5 The liquid crystal composition of Example 5 was prepared according to each compound and weight percentage listed in Table 7, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is shown in the following table:
  • the liquid crystal composition provided by the present invention has the characteristics of high absolute value of negative dielectric anisotropy, high optical anisotropy, good low temperature stability, and fast response speed.
  • the liquid crystal display comprising the liquid crystal composition of the present invention can satisfy the demand of low voltage driving and fast response.
  • liquid crystal composition according to the present invention can be applied to the field of liquid crystals.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
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  • Nonlinear Science (AREA)
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  • Liquid Crystal Substances (AREA)

Abstract

本发明公开了一种液晶组合物及其显示器件，该液晶组合物包含至少一种通式Ⅰ的化合物。本发明还公开了包括本发明的液晶组合物的液晶显示器件。本发明所提供的液晶组合物同时具有高的负介电各向异性的绝对值、高的光学各向异性、较好的低温稳定性以及响应速度快等特点，包含本发明液晶组合物的液晶显示器能够满足低电压驱动、快速响应的需求。

Description

一种液晶组合物及其显示器件 技术领域
本发明涉及液晶材料领域，具体涉及具有负介电各向异性的液晶组合物及其显示器件。
背景技术
液晶显示元件可以在以钟表、电子计算器为代表的家庭用各种电器、测定机器、汽车用面板、文字处理机、电脑、打印机、电视等中使用。根据显示模式的类型分为PC(phase change，相变)、TN(twist nematic，扭曲向列)、STN(super twisted nematic，超扭曲向列)、ECB(electrically controlled birefringence，电控双折射)、OCB(optically compensated bend，光学补偿弯曲)、IPS(in-plane switching，共面转变)、VA(vertical alignment，垂直配向)等类型。根据元件的驱动方式分为PM(passive matrix，被动矩阵)型和AM(active matrix，主动矩阵)型。PM分为静态(static)和多路(multiplex)等类型。AM分为TFT(thin film transistor，薄膜晶体管)、MIM(metal insulator metal，金属-绝缘层-金属)等类型。TFT的类型有非晶硅(amorphous silicon)和多晶硅(polycrystal silicon)。后者根据制造工艺分为高温型和低温型。液晶显示元件根据光源的类型分为利用自然光的反射型、利用背光的透过型、以及利用自然光和背光两种光源的半透过型。
在这些显示方式中，IPS模式、ECB模式、VA模式或CSH模式等与现在常用的TN模式或STN模式的不同在于，前者使用具有负介电各向异性的液晶材料。在这些显示方式中，尤其是VA模式相较于普通的TN模式，其暗态对比度非常好，而且对比度对液晶的双折射、液晶层的厚度和入射光的波长依赖度较小，VA模式在宽视角方面也有很好的表现。除此之外，VA模式也可以省略摩擦的工序，使得成品率上升。对于VA显示模式来说，往往要求液晶组合物具有较大的负介电各向异性的绝对值，还需要具备较高的清亮点、较低的阈值电压和较快的响应时间，此外还需要具有良好的低温稳定性。
然而，现有技术中，很难得到一种同时具备大的光学各向异性、大的负介电各向异性的绝对值、低温稳定性好且响应迅速的液晶组合物。介电各向异性的绝对值大的液晶组合物，临界电压高，消耗的电力也高，响应速度也会相对较慢。因此，为了适应越来越高的应用需求，本领域内存在着持续改进负介电各向异性的液晶化合物的需求。
发明内容
发明目的：针对现有技术的缺陷，本发明的目的在于提供一种具备大的光学各向异性、大的负介电各向异性的绝对值、低温稳定性好且响应迅速的液晶组合物及其显示器件。
本发明的技术方案：
一种液晶组合物，包含：
至少一种通式Ⅰ的化合物
Figure PCTCN2018083330-appb-000001
其中，
R 1和R 2各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
进一步地，在本发明的一些实施方式中，R 2表示含有1-12个碳原子的烷氧基或含有2-12个碳原子的烯氧基，所述含有1-12个碳原子的烷氧基或含有2-12个碳原子的烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
进一步地，在本发明的一些实施方式中，所述液晶组合物包含至少两种所述通式Ⅰ的化合物，且所述通式Ⅰ的化合物占所述液晶组合物总重量的1-35wt％。
进一步地，在本发明的一些实施方式中，所述通式Ⅰ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000002
Figure PCTCN2018083330-appb-000003
以及
Figure PCTCN2018083330-appb-000004
其中，
R 3表示含有1-7个碳原子的烷基或含有2-7个碳原子的烯基；
n表示2-6的整数。
至少两种所述通式Ⅰ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000005
Figure PCTCN2018083330-appb-000006
Figure PCTCN2018083330-appb-000007
以及
Figure PCTCN2018083330-appb-000008
且至少一种所述通式Ⅰ的化合物选自由化合物Ⅰ-a-1至Ⅰ-a-4、Ⅰ-b-1至Ⅰ-b-4及Ⅰ-c组成的组。
进一步地，在本发明的一些实施方式中，所述液晶组合物至少包含两种所述通式Ⅰ的化合物，且所述通式Ⅰ的化合物占所述液晶组合物总重量的5-30wt％。
进一步地，在本发明的一些实施方式中，所述通式Ⅰ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000009
Figure PCTCN2018083330-appb-000010
以及
Figure PCTCN2018083330-appb-000011
其中，
R 3表示含有1-7个碳原子的烷基或含有2-7个碳原子的烯基；
n表示2-6的整数；
且所述通式Ⅰ的化合物占所述液晶组合物总重量的1-35wt％。
再进一步地，在本发明的一些实施方式中，所述通式Ⅰ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000012
Figure PCTCN2018083330-appb-000013
以及
Figure PCTCN2018083330-appb-000014
其中，
R 3表示含有1-7个碳原子的烷基或含有2-7个碳原子的烯基；
n表示2-6的整数；
且所述通式Ⅰ的化合物占所述液晶组合物总重量的5-30wt％。
进一步地，在本发明的一些实施方式中，还包含至少一种通式Ⅱ的化合物
Figure PCTCN2018083330-appb-000015
其中，
R 4和R 5各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代；
环
Figure PCTCN2018083330-appb-000016
表示
Figure PCTCN2018083330-appb-000017
所述
Figure PCTCN2018083330-appb-000018
中的一个或多个-CH 2- 可被-O-替代，所述
Figure PCTCN2018083330-appb-000019
中的一个或多个H可被F取代；
Z 1表示单键、-CH 2O-、-CF 2O-或-COO-；
m表示0或1。
进一步地，所述通式Ⅱ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000020
Figure PCTCN2018083330-appb-000021
以及
Figure PCTCN2018083330-appb-000022
其中，
R 41和R 51各自独立的表示含有1-7个碳原子的烷基或烷氧基或含有2-7个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
再进一步地，所述通式Ⅱ-1的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000023
Figure PCTCN2018083330-appb-000024
Figure PCTCN2018083330-appb-000025
以及
Figure PCTCN2018083330-appb-000026
所述通式Ⅱ-2的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000027
Figure PCTCN2018083330-appb-000028
Figure PCTCN2018083330-appb-000029
以及
Figure PCTCN2018083330-appb-000030
所述通式Ⅱ-3的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000031
Figure PCTCN2018083330-appb-000032
Figure PCTCN2018083330-appb-000033
以及
Figure PCTCN2018083330-appb-000034
所述通式Ⅱ-4的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000035
Figure PCTCN2018083330-appb-000036
以及
Figure PCTCN2018083330-appb-000037
所述通式Ⅱ-5的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000038
Figure PCTCN2018083330-appb-000039
Figure PCTCN2018083330-appb-000040
以及
Figure PCTCN2018083330-appb-000041
所述通式Ⅱ-6的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000042
Figure PCTCN2018083330-appb-000043
Figure PCTCN2018083330-appb-000044
以及
Figure PCTCN2018083330-appb-000045
进一步地，在本发明的一些实施方式中，还包含至少一种通式Ⅲ的化合物
Figure PCTCN2018083330-appb-000046
其中，
R 6和R 7各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代；
环
Figure PCTCN2018083330-appb-000047
和环
Figure PCTCN2018083330-appb-000048
各自独立的表示
Figure PCTCN2018083330-appb-000049
Z 2表示单键、-CH 2O-、-CF 2O-或-COO-；
p表示0或1。
进一步地，所述通式Ⅲ的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000050
Figure PCTCN2018083330-appb-000051
以及
Figure PCTCN2018083330-appb-000052
其中，
R 61和R 71各自独立的表示含有1-7个碳原子的烷基或烷氧基或含有2-7个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
再进一步地，所述通式Ⅲ-1的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000053
Figure PCTCN2018083330-appb-000054
Figure PCTCN2018083330-appb-000055
以及
Figure PCTCN2018083330-appb-000056
所述通式Ⅲ-2的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000057
Figure PCTCN2018083330-appb-000058
Figure PCTCN2018083330-appb-000059
以及
Figure PCTCN2018083330-appb-000060
所述通式Ⅲ-3的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000061
Figure PCTCN2018083330-appb-000062
以及
Figure PCTCN2018083330-appb-000063
所述通式Ⅲ-4的化合物选自由如下化合物组成的组：
Figure PCTCN2018083330-appb-000064
Figure PCTCN2018083330-appb-000065
以及
Figure PCTCN2018083330-appb-000066
一种包含上述液晶组合物的液晶显示器件。
进一步地，所述液晶组合物还包含本领域技术人员已知和文献中描述的一种或多种添加剂。
如下提及例如可以加入到根据本发明的混合物中的稳定剂。
Figure PCTCN2018083330-appb-000067
Figure PCTCN2018083330-appb-000068
Figure PCTCN2018083330-appb-000069
在本发明的实施方案中，优选地，所述稳定剂占所述液晶组合物总重量的0-5wt％；更优选地，所述稳定剂占所述液晶组合物总重量的0-1wt％；作为特别优选方案，所述稳定剂占所述液晶组合物总重量的0.01-0.1wt％。
本发明另一方面还提供一种液晶显示器，其包含本发明所提供的液晶组合物。
有益效果：
本发明所提供的液晶组合物同时具有高的负介电各向异性的绝对值、高的光学各向异性、较好的低温稳定性以及响应速度快等特点，包含本发明液晶组合物的液晶显示器能够满足低电压驱动、快速响应的需求。
具体实施方式
以下将结合具体实施方案来说明本发明。需要说明的是，下面的实施例为本发明的示例，仅用来说明本发明，而不用来限制本发明。在不偏离本发明主旨或范围的情况下，可进行本发明构思内的其他组合和各种改良。
在本发明中如无特殊说明，所述的比例均为重量比，所有温度均为摄氏度温度。
为便于表达，以下各实施例中，液晶组合物的基团结构用表1所列的代码表示：
表1液晶化合物的基团结构代码
Figure PCTCN2018083330-appb-000070
以如下结构式的化合物为例：
Figure PCTCN2018083330-appb-000071
该结构式如用表1所列代码表示，则可表达为：nCCGF，代码中的n表示左端烷基的C原子数，例如n为“3”，即表示该烷基为-C 3H 7；代码中的C代表环己烷基，G代表2-氟-1,4-亚苯基，F代表氟。
以下实施例中测试项目的简写代号如下：
Figure PCTCN2018083330-appb-000072
其中，
光学各向异性使用阿贝折光仪在钠光灯(589nm)光源下、25℃测试得。
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：25℃、1KHz、测试盒为TN90型，盒厚7μm。
γ1使用TOYO6254型液晶物性评价系统测试得到；测试温度为25℃，测试电压为90V。
在以下的实施例中所采用的各成分，均可以通过公知的方法进行合成，或者通过商业途径获得。这些合成技术是常规的，所得到各液晶化合物经测试符合电子类化合物标准。
按照以下实施例规定的各液晶组合物的配比，制备液晶组合物。所述液晶组合物的制备是按照本领域的常规方法进行的，如采取加热、超声波、悬浮等方式按照规定比例混合制得。
制备并研究下列实施例中给出的液晶组合物。下面显示了各液晶组合物的组成和其性能参数测试结果。
对比例1
按表2中所列的各化合物及重量百分数配制成对比例1的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表2液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000073
Figure PCTCN2018083330-appb-000074
实施例1
按表3中所列的各化合物及重量百分数配制成实施例1的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表3液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000075
实施例2
按表4中所列的各化合物及重量百分数配制成实施例2的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表4液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000076
Figure PCTCN2018083330-appb-000077
实施例3
按表5中所列的各化合物及重量百分数配制成实施例3的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表5液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000078
实施例4
按表6中所列的各化合物及重量百分数配制成实施例4的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表6液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000079
实施例5
按表7中所列的各化合物及重量百分数配制成实施例5的液晶组合物，其填充于液晶显示器两基板之间进行性能测试，测试数据如下表所示：
表7液晶组合物配方及其测试性能
Figure PCTCN2018083330-appb-000080
Figure PCTCN2018083330-appb-000081
从以上实施例的数据可知，本发明所提供的液晶组合物同时具有高的负介电各向异性的绝对值、高的光学各向异性、较好的低温稳定性以及响应速度快等特点，包含本发明液晶组合物的液晶显示器能够满足低电压驱动、快速响应的需求。
以上实施方式只为说明本发明的技术构思及特点，其目的在于让熟悉此项技术的人了解本发明内容并加以实施，并不能以此限制本发明的保护范围，凡根据本发明精神实质所做的等效变化或修饰，都应涵盖在本发明的保护范围内。
工业实用性
本发明所涉及的液晶组合物可以应用于液晶领域。

Claims (12)

  1. 一种液晶组合物，其特征在于，包含：
    至少一种通式Ⅰ的化合物
    Figure PCTCN2018083330-appb-100001
    其中，
    R 1和R 2各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
  2. 根据权利要求1所述的液晶组合物，其特征在于，R 2表示含有1-12个碳原子的烷氧基或含有2-12个碳原子的烯氧基，所述含有1-12个碳原子的烷氧基或含有2-12个碳原子的烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代。
  3. 根据权利要求2所述的液晶组合物，其特征在于，所述通式Ⅰ的化合物选自由如下化合物组成的组：
    Figure PCTCN2018083330-appb-100002
    Figure PCTCN2018083330-appb-100003
    以及
    Figure PCTCN2018083330-appb-100004
    其中，
    R 3表示含有1-7个碳原子的烷基或含有2-7个碳原子的烯基；
    n表示2-6的整数。
  4. 根据权利要求1所述的液晶组合物，其特征在于，所述液晶组合物包含至少两种所述通式Ⅰ的化合物，且所述通式Ⅰ的化合物占所述液晶组合物总重量的1-35wt％。
  5. 根据权利要求4所述的液晶组合物，其特征在于，至少一种所述通式Ⅰ的化合物选自由如下化合物组成的组：
    Figure PCTCN2018083330-appb-100005
    Figure PCTCN2018083330-appb-100006
    以及
    Figure PCTCN2018083330-appb-100007
    其中，
    R 3表示含有1-7个碳原子的烷基或含有2-7个碳原子的烯基；
    n表示2-6的整数。
  6. 根据权利要求5所述的液晶组合物，其特征在于，至少两种所述通式Ⅰ的化合物选自由如下化合物组成的组：
    Figure PCTCN2018083330-appb-100008
    Figure PCTCN2018083330-appb-100009
    Figure PCTCN2018083330-appb-100010
    以及
    Figure PCTCN2018083330-appb-100011
    且至少一种所述通式Ⅰ的化合物选自由化合物Ⅰ-a-1至Ⅰ-a-4、Ⅰ-b-1至Ⅰ-b-4及Ⅰ-c组成的组。
  7. 根据权利要求4所述的液晶组合物，其特征在于，所述通式Ⅰ的化合物占所述液晶组合物总重量的5-30wt％。
  8. 根据权利要求3所述的液晶组合物，其特征在于，所述通式Ⅰ的化合物占所述液晶组合物总重量的1-35wt％。
  9. 根据权利要求8所述的液晶组合物，其特征在于，所述通式Ⅰ的化合物占所述液晶组合物总重量的5-30wt％。
  10. 根据权利要求7或9所述的一种液晶组合物，其特征在于，还包含至少一种通式Ⅱ的化合物
    Figure PCTCN2018083330-appb-100012
    其中，
    R 4和R 5各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代；
    环
    Figure PCTCN2018083330-appb-100013
    表示
    Figure PCTCN2018083330-appb-100014
    或
    Figure PCTCN2018083330-appb-100015
    所述
    Figure PCTCN2018083330-appb-100016
    中的一个或多个-CH 2-可被-O-替代，所述
    Figure PCTCN2018083330-appb-100017
    中的一个或多个H可被F取代；
    Z 1表示单键、-CH 2O-、-CF 2O-或-COO-；
    m表示0或1。
  11. 根据权利要求10所述的液晶组合物，其特征在于，还包含至少一种通式Ⅲ的化合物
    Figure PCTCN2018083330-appb-100018
    其中，
    R 6和R 7各自独立的表示含有1-12个碳原子的烷基或烷氧基或含有2-12个碳原子的烯基或烯氧基，其中所述烷基或烷氧基和所述烯基或烯氧基中的一个或多个不相邻的-CH 2-可以以氧原子不直接相连的方式各自独立地被-O-替代；
    环
    Figure PCTCN2018083330-appb-100019
    和环
    Figure PCTCN2018083330-appb-100020
    各自独立的表示
    Figure PCTCN2018083330-appb-100021
    Z 2表示单键、-CH 2O-、-CF 2O-或-COO-；
    p表示0或1。
  12. 一种包含权利要求1～11任一项所述液晶组合物的液晶显示器件。
PCT/CN2018/083330 2017-04-18 2018-04-17 一种液晶组合物及其显示器件 WO2018192476A1 (zh)

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