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WO2022068499A1 - 含噻吩的液晶化合物及其制备方法和应用 - Google Patents

含噻吩的液晶化合物及其制备方法和应用 Download PDF

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WO2022068499A1
WO2022068499A1 PCT/CN2021/115383 CN2021115383W WO2022068499A1 WO 2022068499 A1 WO2022068499 A1 WO 2022068499A1 CN 2021115383 W CN2021115383 W CN 2021115383W WO 2022068499 A1 WO2022068499 A1 WO 2022068499A1
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liquid crystal
thiophene
containing liquid
crystal compound
compound according
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PCT/CN2021/115383
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English (en)
French (fr)
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朱波
戴雄
边坤
程友文
吕永清
王静
王学涛
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北京八亿时空液晶科技股份有限公司
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Publication of WO2022068499A1 publication Critical patent/WO2022068499A1/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
    • C09K19/06—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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 belongs to the technical field of liquid crystal materials, and particularly relates to a thiophene-containing liquid crystal compound and a preparation method and application thereof.
  • liquid crystals are widely used in the field of information display, and some progress has also been made in the application of optical communication (S.T.Wu, D.K.Yang.Reflective Liquid Crystal Displays.Wiley, 2001).
  • optical communication S.T.Wu, D.K.Yang.Reflective Liquid Crystal Displays.Wiley, 2001.
  • the application fields of liquid crystal compounds have been significantly expanded to various display devices, electro-optical devices, electronic components, sensors, and the like.
  • many different structures have been proposed, especially in the field of nematic liquid crystals, and nematic liquid crystal compounds have so far been the most widely used in flat panel displays. Especially in TFT active matrix systems.
  • TFT-LCD has been widely used in direct-view TV, large-screen projection TV, computer terminal display and some military instrument display. It is believed that TFT-LCD technology has a broader application prospect.
  • TFT-LCD product technology has matured, successfully solved technical problems such as viewing angle, resolution, color saturation and brightness, and its display performance has approached or exceeded CRT displays.
  • Large size and small and medium size TFT-LCD displays have gradually occupied the mainstream position of flat panel displays in their respective fields.
  • TFT-LCD still has many defects such as insufficient response, low voltage, and insufficient charge retention.
  • liquid crystal media For liquid crystal media, a fast response time is required, and reducing the thickness of the liquid crystal can shorten the response time, which requires a high optical dielectric constant ⁇ n to ensure sufficient optical retardation value d* ⁇ n, however, a high optical dielectric constant
  • the liquid crystal of ⁇ n generally has a high rotational viscosity, which in turn leads to a longer response time.
  • the first object of the present invention is to provide a novel thiophene-containing liquid crystal compound, which has high optical anisotropy and low rotational viscosity, and can improve the response time of liquid crystal display devices.
  • the thiophene-containing liquid crystal compound has a structure represented by the general formula (I):
  • R 2 represents -H, a C 1 -C 15 alkyl group, a C 1 -C 15 alkoxy group, a C 2 -C 15 alkenyl group or a C 2 -C 15 alkenyloxy group, wherein the C 1 -C 15 alkenyl group
  • a 1 represents a single bond or one of the following groups:
  • a 2 represents a single bond or one of the following groups:
  • n 0, 1, 2, 3 or 4.
  • R 1 and R 2 each independently represent H, a C 1 -C 7 alkyl group or a C 1 -C 7 alkoxy group, and the C 1 -C 7
  • One or more hydrogens in an alkyl or C1 - C7 alkoxy group may be optionally substituted by fluorine or chlorine, preferably by fluorine.
  • a 1 represents a single bond or one of the following groups:
  • Z 1 and Z 2 each independently represent a single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -COO-, -OOC- , -OCH2- , -CH2O- , -CF2O- or -OCF2- .
  • the thiophene-containing liquid crystal compound is selected from one or more of the following structures:
  • Another object of the present invention is to provide the preparation method of the above-mentioned liquid crystal compound containing thiophene, and its synthetic route is as follows:
  • R 1 , R 2 , A 1 , A 2 , Z 1 , Z 2 , and n in the compounds involved in the above steps are as defined above.
  • the third object of the present invention is to protect a liquid crystal composition containing the above-mentioned thiophene-containing liquid crystal compound.
  • the addition amount of the above-mentioned thiophene-containing liquid crystal compound is preferably 1-80%, more preferably 3-50%.
  • Those skilled in the art can predict that the addition of the above-mentioned thiophene-containing liquid crystal compound can further improve the optical anisotropy of the existing conventional liquid crystal composition, and has the technical effect of shortening the response time of the device.
  • the fourth object of the present invention is to protect the application of the above-mentioned thiophene-containing liquid crystal compound and the composition containing the above-mentioned thiophene-containing liquid crystal compound in the field of liquid crystal display.
  • Preferred is the application in liquid crystal display devices.
  • the liquid crystal display device includes but is not limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display. After the above-mentioned thiophene-containing liquid crystal composition is applied to a liquid crystal display device, it has the technical effect of shortening the response time of the device.
  • the percentages in the present invention are by weight; the temperature is in degrees Celsius.
  • the synthetic route is as follows:
  • Mass spectrometry fragment 382.1 (molecular ion peak).
  • the synthetic route is as follows:
  • Mass spectrometry fragment 458.2 (molecular ion peak).
  • the synthetic route is as follows:
  • Mass spectrometry fragment 466.2 (molecular ion peak).
  • This experimental example involves the determination of the relevant properties of the compounds described in Examples 1-9.
  • the detection of ⁇ 1 is measured by a viscometer
  • the detection of ⁇ n is measured by an Abbe refractometer
  • the detection of ⁇ is measured by a capacitive reactance tester HP-4284A of Hewlett-Packard Company.
  • the present invention provides a liquid crystal compound containing thiophene, a preparation method and application thereof.
  • the thiophene-containing liquid crystal compound has a structure represented by the general formula (I), which has high optical anisotropy and low rotational viscosity, thereby improving the response time, and has good economic value and application prospect.

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Abstract

属于液晶材料技术领域，具体涉及一种含噻吩的液晶化合物及其制备方法和应用。所述含噻吩的液晶化合物具有如通式(I)所示的结构，其具有较高的光学各向异性和低的旋转粘度，从而改善响应时间。

Description

[根据细则37.2由ISA制定的发明名称]　含噻吩的液晶化合物及其制备方法和应用
交叉引用
本申请要求2020年9月30日提交的专利名称为“一种含噻吩的液晶化合物及其制备方法和应用”的第202011065605.0号中国专利申请的优先权，其全部公开内容通过引用整体并入本文。
技术领域
本发明属于液晶材料技术领域，具体涉及一种含噻吩的液晶化合物及其制备方法和应用。
背景技术
目前，液晶在信息显示领域得到广泛应用，同时在光通讯中的应用也取得了一定的进展(S.T.Wu，D.K.Yang.Reflective Liquid Crystal Displays.Wiley，2001)。近几年，液晶化合物的应用领域已经显著拓宽到各类显示器件、电光器件、电子元件、传感器等。为此，已经提出许多不同的结构，特别是在向列型液晶领域，向列型液晶化合物迄今已经在平板显示器中得到最为广泛的应用。特别是用于TFT有源矩阵的系统中。
彩色显示大多采用有源矩阵显示方式。TFT-LCD已经广泛用于直视型电视、大屏幕投影电视、计算机终端显示和某些军用仪表显示，相信TFT-LCD技术具有更为广阔的应用前景。
目前，TFT-LCD产品技术已经成熟，成功地解决了视角、分辨率、色饱和度和亮度等技术难题，其显示性能已经接近或超过CRT显示器。大尺寸和中小尺寸TFT-LCD显示器在各自的领域已逐渐占据平板显示器的主流地位。但是因受液晶材料本身的限制，TFT-LCD仍然存在着响应不够快，电压不够低，电荷保持率不够高等诸多缺陷。
对于液晶介质来说，需要快速的响应时间，减少液晶的厚度可以缩短反应时间，这就需要高的光学介电常数Δn以保证足够的光延迟值d*Δn,然而有高的光学介电常数Δn的液晶一般具有高的旋转粘度，又导致响应时间变长。
因此寻找低粘度、高光学各向异性的单晶化合物尤为重要。
发明内容
本发明的第一目的是提供一种新型的含噻吩的液晶化合物，该化合物具有较高的光学各向异性和低的旋转粘度，可以改善液晶显示器件的响应时间。
所述含噻吩的液晶化合物具有如通式(I)所示的结构：
Figure PCTCN2021115383-appb-000001
式中，
R 1表示-H、-Cl、-F、-CN、-OCN、-OCF 3、-CF 3、-CHF 2、-CH 2F、-OCHF 2、-OCF＝CF 2，-OCF 2CF 3，-SCN、-NCS、-SF 5、C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基，其中所述C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基中的一个或多个氢可任选地被氟或氯取代，且一个或多个不相邻的-CH 2-可彼此独立地被-CH＝CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代；
R 2表示-H、C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基，其中所述C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基中的一个或多个氢可任选地被氟或氯 取代，且一个或多个不相邻的-CH 2-可彼此独立地被-CH＝CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代；
A 1代表单键或下列基团中的一种：
Figure PCTCN2021115383-appb-000002
A 2代表单键或下列基团中的一种：
Figure PCTCN2021115383-appb-000003
Z 1、Z 2各自独立地表示单键、-CH 2-、-CH 2-CH 2-、-(CH 2) 3-、-(CH 2) 4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-OCH 2-、-CH 2O-、-CF 2O-、-OCF 2-、-CF 2CH 2-、-CH 2CF 2-、-C 2F 4-或-CF＝CF-；
n＝0、1、2、3或4。
优选的，上述含噻吩的液晶化合物中，R 1，R 2各自独立地表示H、C 1-C 7的烷基或C 1-C 7的烷氧基，且所述C 1-C 7的烷基或C 1-C 7的烷氧基中的一个或多个氢可任选地被氟或氯取代，优选被氟取代。
优选的，上述含噻吩的液晶化合物中，A 1代表单键或下列基团中的一种：
Figure PCTCN2021115383-appb-000004
优选的，上述含噻吩的液晶化合物中，Z 1、Z 2各自独立地表示单键、-CH 2-、-CH 2-CH 2-、-(CH 2) 3-、-(CH 2) 4-、-COO-、-OOC-、-OCH 2-、-CH 2O-、-CF 2O-或-OCF 2-。
作为进一步优选的技术方案，所述含噻吩的液晶化合物选自以下结构中的一种或多种：
Figure PCTCN2021115383-appb-000005
Figure PCTCN2021115383-appb-000006
Figure PCTCN2021115383-appb-000007
Figure PCTCN2021115383-appb-000008
Figure PCTCN2021115383-appb-000009
Figure PCTCN2021115383-appb-000010
Figure PCTCN2021115383-appb-000011
Figure PCTCN2021115383-appb-000012
Figure PCTCN2021115383-appb-000013
Figure PCTCN2021115383-appb-000014
Figure PCTCN2021115383-appb-000015
Figure PCTCN2021115383-appb-000016
Figure PCTCN2021115383-appb-000017
Figure PCTCN2021115383-appb-000018
Figure PCTCN2021115383-appb-000019
Figure PCTCN2021115383-appb-000020
Figure PCTCN2021115383-appb-000021
Figure PCTCN2021115383-appb-000022
Figure PCTCN2021115383-appb-000023
Figure PCTCN2021115383-appb-000024
Figure PCTCN2021115383-appb-000025
Figure PCTCN2021115383-appb-000026
Figure PCTCN2021115383-appb-000027
Figure PCTCN2021115383-appb-000028
Figure PCTCN2021115383-appb-000029
Figure PCTCN2021115383-appb-000030
本发明的另一目的是提供上述含噻吩的液晶化合物的制备方法，其合成路线如下：
Figure PCTCN2021115383-appb-000031
具体包括如下步骤：
化合物I-1-01与化合物I-1-02，在碳酸钠以及催化剂作用下反应得到目标化合物I；
其中，上述步骤所涉及化合物中的R 1、R 2、A 1、A 2、Z 1、Z 2、n的定义同上。
本发明的第三目的是保护含有上述含噻吩的液晶化合物的液晶组合物。其中，上述含噻吩的液晶化合物的加入量以1-80％为宜，更优选3-50％。本领域技术人员可以预见，基于上述含噻吩的液晶化合物的加入，能够进一步提高已有惯用液晶组合物的光学各向异性，具有缩短器件的响应时间的技术效果。
本发明的第四目的是保护上述含噻吩的液晶化合物以及含有上述含噻吩的液晶化合物的组合物在液晶显示领域的应用。优选为在液晶显示装置中的应用。所述的液晶显示装置包括但并不限于TN、ADS、VA、PSVA、FFS或IPS液晶显示器。将上述含噻吩的液晶组合物应用至液晶显示装置后，具有缩短器件的响应时间的技术效果。
具体实施方式
以下实施例用于说明本发明，但不用来限制本发明的范围。
除非另有说明，本发明中百分比为重量百分比；温度单位为摄氏度。
实施例1：
Figure PCTCN2021115383-appb-000032
合成路线如下：
Figure PCTCN2021115383-appb-000033
在反应瓶中加入27.6g(0.1mol)化合物BYLC-01-1(反应物)，24gBYLC-01-2(反应物)100ml甲苯(溶剂)，100ml乙醇，100ml水，通氮气保护，加入1g四三苯基膦钯，12g碳酸钠，加热回流反应6小时，分液，100ml甲苯(溶剂)提取水相，水洗有机相至中性，蒸干溶剂得淡黄色固体，200ml乙醇200ml正庚烷重结晶两次得34.3gBYLC-01，收率90％，气相色谱纯度99.8％。
质谱分析碎片：382.1(分子离子峰)。
实施例2
Figure PCTCN2021115383-appb-000034
合成路线如下：
Figure PCTCN2021115383-appb-000035
在反应瓶中加入35.2g(0.1mol)化合物BYLC-02-1(反应物)，24gBYLC-01-2,100ml甲苯(溶剂)，100ml乙醇，100ml水，通氮气保护，加入1g四三苯基膦钯，12g碳酸钠，加热回流反应6小时，分液，100ml甲苯(溶剂)提取水相，水洗有机相至中性，蒸干溶剂得淡黄色固体，200ml乙醇200ml正庚烷重结晶两次得38.9gBYLC-02，收率85％，气相色谱纯度99.8％。
质谱分析碎片：458.2(分子离子峰)。
实施例3
Figure PCTCN2021115383-appb-000036
合成路线如下：
Figure PCTCN2021115383-appb-000037
在反应瓶中加入36g(0.1mol)化合物BYLC-03-1(反应物)，24gBYLC-01-2,100ml甲苯(溶剂)，100ml乙醇，100ml水，通氮气保护，加入1g四三苯基膦钯，12g碳酸钠，加热回流反应6小时，分液，100ml甲苯(溶剂)提取水相，水洗有机相至中性，蒸干溶剂得淡黄色固体，200ml乙醇200ml正庚烷重结晶两次得40gBYLC-03，收率86％，气相色谱纯度99.8％。
质谱分析碎片：466.2(分子离子峰)。
实施例4
Figure PCTCN2021115383-appb-000038
采用GC-MS对所得白色固体BYLC-04进行分析，产物的m/z为368.1(M+)。
实施例5
Figure PCTCN2021115383-appb-000039
采用GC-MS对所得白色固体BYLC-05进行分析，产物的m/z为354.1(M+)。
实施例6
Figure PCTCN2021115383-appb-000040
采用GC-MS对所得白色固体BYLC-06进行分析，产物的m/z为408.1(M+)。
实施例7
Figure PCTCN2021115383-appb-000041
采用GC-MS对所得白色固体BYLC-07进行分析，产物的m/z为380.1(M+)。
实施例8
Figure PCTCN2021115383-appb-000042
采用GC-MS对所得白色固体BYLC-08进行分析，产物的m/z为412.1(M+)。
实施例9
Figure PCTCN2021115383-appb-000043
采用GC-MS对所得白色固体BYLC-09进行分析，产物的m/z为396.1(M+)。
实验例
本实验例涉及对实施例1～9所述化合物的相关性能测定。
按照本领域的常规检测方法，γ1的检测采用粘度计测试，△n的检测采用阿贝折射仪测试，△ε的检测采用惠普公司型号为HP-4284A的电容电抗测试仪进行测定。
通过线性拟合得到液晶化合物的各项性能参数，其中，各性能参数的具体含义如下：
△n代表光学各向异性(25℃)；γ1代表旋转粘度(mPa.s，25℃)；△ε代表介电各向异性(25℃，1000Hz)。
将实施例1～9所制得的液晶化合物和对比例1～2液晶化合物的性能参数数据进行对比整理，检测 结果如表1所示：
表1：液晶化合物的性能检测结果
Figure PCTCN2021115383-appb-000044
Figure PCTCN2021115383-appb-000045
由表1的检测结果可以明显看出，本发明提供的含噻吩的液晶化合物与传统的相似化学结构化合物相比，具有较高的光学各向异性△n，低的旋转粘度γ1，从而很好的改善响应时间。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。
工业实用性
本发明提供一种含噻吩的液晶化合物及其制备方法和应用。所述含噻吩的液晶化合物具有如通式(I)所示的结构，其具有较高的光学各向异性和低的旋转粘度，从而改善响应时间，具有较好的经济价值和应用前景。
Figure PCTCN2021115383-appb-000046

Claims (10)

  1. 一种含噻吩的液晶化合物，其特征在于，具有如通式(I)所示的结构：
    Figure PCTCN2021115383-appb-100001
    式中，
    R 1表示-H、-Cl、-F、-CN、-OCN、-OCF 3、-CF 3、-CHF 2、-CH 2F、-OCHF 2、-OCF＝CF 2，-OCF 2CF 3，-SCN、-NCS、-SF 5、C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基，其中所述C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基中的一个或多个氢可任选地被氟或氯取代，且一个或多个不相邻的-CH 2-可彼此独立地被-CH＝CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代；
    R 2表示-H、C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基，其中所述C 1-C 15的烷基、C 1-C 15的烷氧基、C 2-C 15的烯基或C 2-C 15的烯氧基中的一个或多个氢可任选地被氟或氯取代，且一个或多个不相邻的-CH 2-可彼此独立地被-CH＝CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代；
    A 1代表单键或下列基团中的一种：
    Figure PCTCN2021115383-appb-100002
    A 2代表单键或下列基团中的一种：
    Figure PCTCN2021115383-appb-100003
    Z 1、Z 2各自独立地表示单键、-CH 2-、-CH 2-CH 2-、-(CH 2) 3-、-(CH 2) 4-、-CH＝CH-、 -C≡C-、-COO-、-OOC-、-OCH 2-、-CH 2O-、-CF 2O-、-OCF 2-、-CF 2CH 2-、-CH 2CF 2-、-C 2F 4-或-CF＝CF-；
    n＝0、1、2、3或4。
  2. 根据权利要求1所述的含噻吩的液晶化合物，其特征在于，R 1，R 2各自独立地表示H、C 1-C 7的烷基或C 1-C 7的烷氧基，且所述C 1-C 7的烷基或C 1-C 7的烷氧基中的一个或多个氢可任选地被氟或氯取代，优选被氟取代。
  3. 根据权利要求1或2所述的含噻吩的液晶化合物，其特征在于，A 1代表单键或下列基团中的一种：
    Figure PCTCN2021115383-appb-100004
  4. 根据权利要求1-3任一项所述的含噻吩的液晶化合物，其特征在于，Z 1、Z 2各自独立地表示单键、-CH 2-、-CH 2-CH 2-、-(CH 2) 3-、-(CH 2) 4-、-COO-、-OOC-、-OCH 2-、-CH 2O-、-CF 2O-或-OCF 2-。
  5. 根据权利要求1所述的含噻吩的液晶化合物，其特征在于，所述通式(I)代表的化合物选自以下结构中的一种或多种：
    Figure PCTCN2021115383-appb-100005
    Figure PCTCN2021115383-appb-100006
    Figure PCTCN2021115383-appb-100007
    Figure PCTCN2021115383-appb-100008
    Figure PCTCN2021115383-appb-100009
    Figure PCTCN2021115383-appb-100010
    Figure PCTCN2021115383-appb-100011
    Figure PCTCN2021115383-appb-100012
    Figure PCTCN2021115383-appb-100013
    Figure PCTCN2021115383-appb-100014
    Figure PCTCN2021115383-appb-100015
    Figure PCTCN2021115383-appb-100016
    Figure PCTCN2021115383-appb-100017
    Figure PCTCN2021115383-appb-100018
    Figure PCTCN2021115383-appb-100019
    Figure PCTCN2021115383-appb-100020
    Figure PCTCN2021115383-appb-100021
    Figure PCTCN2021115383-appb-100022
    Figure PCTCN2021115383-appb-100023
    Figure PCTCN2021115383-appb-100024
    Figure PCTCN2021115383-appb-100025
    Figure PCTCN2021115383-appb-100026
    Figure PCTCN2021115383-appb-100027
    Figure PCTCN2021115383-appb-100028
    Figure PCTCN2021115383-appb-100029
    Figure PCTCN2021115383-appb-100030
  6. 权利要求1～5任一项所述的含噻吩的液晶化合物的制备方法，其特征在于，其合成路线如下：
    Figure PCTCN2021115383-appb-100031
    具体包括如下步骤：
    化合物I-1-01与化合物I-1-02，在碳酸钠以及催化剂作用下反应得到目标化合物 I；
    其中，R 1、R 2、A 1、A 2、Z 1、Z 2、n的指代同权利要求1-4任一项所述。
  7. 一种液晶组合物，其特征在于，包括权利要求1～5任一项所述的含噻吩的液晶化合物。
  8. 根据权利要求7所述的液晶组合物，其特征在于，所述含噻吩的液晶化合物在所述液晶组合物中的质量百分比为1～60％，优选为3～50％，进一步优选为5～25％。
  9. 权利要求1～5任一项所述的含噻吩的液晶化合物或权利要求7或8所述的液晶组合物在液晶显示装置中的应用。
  10. 根据权利要求9所述的应用，其特征在于，所述液晶显示领域为液晶显示装置，优选的，所述液晶显示装置为TN、ADS、VA、PSVA、FFS或IPS液晶显示器。
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