Liquid crystal composition and liquid crystal display element and liquid crystal display comprising the same
Patent Information
- Application Number
- CN202611114737.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-07-24
- Publication Date
- 2026-08-21
AI Technical Summary
然而,随着显示技术的迭代升级,现有液晶材料在响应速度方面的性能瓶颈日益凸显,亟需开发响应速度更快的新型分子结构,以满足日益严苛的动态显示需求
本发明提供的液晶组合物具有较低的γ1、较小的γ1/K11,以及较小的K11/Δε绝对值,可以用于开发响应速度快、阈值电压低的液晶显示元件、液晶显示器。
Smart Images

Figure CN122609252A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of liquid crystal display technology. More specifically, it relates to a liquid crystal composition and a liquid crystal display element or liquid crystal display comprising the liquid crystal composition. Background Technology
[0002] Liquid crystal materials, as important electro-optic functional materials, began their modern application in the mid-20th century. In 1968, RCA Corporation in the United States developed the first liquid crystal display based on dynamic scattering modes. Since then, it has undergone evolutions such as guest-host and twisted nematic types, laying the foundation for modern display technology. In this development process, thin-film transistor (TFT) active matrix technology, with its advantage of independently controlling each sub-pixel, has achieved high contrast, fast response, and high resolution, becoming the core technology driving the leap in liquid crystal display performance.
[0003] Display modes based on the electro-optic effect of liquid crystals have undergone multiple technological iterations, resulting in a landscape of parallel development of various commercial technologies. Twisted Nematic (TN) mode was the earliest commercially viable display mode. It utilizes the twisting and alignment of liquid crystal molecules under an electric field to achieve optical switching, offering advantages such as fast response speed and low driving voltage, but with poor viewing angle characteristics. Vertical Alignment (VA) mode utilizes the tilting behavior of negative liquid crystals under a vertical electric field, and with the aid of a compensation film, it can achieve high contrast and wide viewing angle, dominating the large-screen television market. In-Plane Switching (IPS) mode and its derivative Edge Field Switching (FFS) mode place electrodes on the same substrate, using a horizontal electric field parallel to the substrate to drive liquid crystal molecules to rotate in-plane, thereby achieving extremely wide viewing angles and excellent color performance. It has become the mainstream choice for mobile terminal devices such as smartphones and tablets. Furthermore, emerging technologies such as Blue Phase Liquid Crystal Display (BPLCD) and electrowetting are under continuous exploration, but key bottlenecks such as material stability and driving voltage still need to be overcome before large-scale mass production.
[0004] With the increasing prevalence of dynamic visual content (such as high-definition video and 3D games) and the widespread adoption of high refresh rate display panels, the demands on the response speed of liquid crystal materials are becoming increasingly stringent. The response time of a liquid crystal is determined by both the cell thickness (d) and the physical properties of the liquid crystal material, and is essentially constrained by the interplay between rotational viscosity (γ1), elastic constant, and cell thickness. To achieve faster response times, there are currently two main technical approaches: First, while maintaining a constant cell thickness, it is necessary to minimize the γ1 of the liquid crystal material and optimize its relationship with the elastic constant (K). 11 The ratio of γ1 / K 11One approach is to accelerate the elastic recovery of liquid crystal molecules after the electric field is removed. Another approach is to directly shorten the response time by reducing the cell thickness (d), but this significantly weakens the optical path difference (Δnd), leading to a decrease in panel transmittance. Therefore, it is necessary to simultaneously increase the birefringence (Δn) of the liquid crystal material to compensate for the optical transmission loss caused by the low cell thickness, thereby maintaining the original brightness level while leveraging the speed advantage of low cell thickness. Thus, the core direction of liquid crystal material development for fast response lies in the coordinated pursuit of low γ1 and low γ1 / K. 11 And the combination of high Δn physical properties, thereby breaking through the dual bottlenecks of response speed and display brightness.
[0005] Furthermore, the widespread application of liquid crystal displays (LCDs) in portable electronic devices, IoT terminals, and automotive displays has placed increasingly stringent demands on their energy efficiency. Threshold voltage is a key electro-optic parameter determining the driving voltage level of an LCD, directly affecting the overall power consumption of the device. A lower threshold voltage allows for a corresponding reduction in the addressing and operating voltages required by the device, effectively reducing energy consumption and extending battery life. For liquid crystal materials, the elastic constant K and dielectric anisotropy Δε are two core physical properties determining the threshold voltage. The ratio K / Δε is widely used as an effective indicator for evaluating the threshold voltage of liquid crystal materials. A smaller K / Δε value indicates a lower threshold voltage. Based on this principle, reducing the K / Δε ratio through molecular design and component formulation has become a key technical strategy for developing low-voltage, low-energy liquid crystal compositions. Therefore, providing a liquid crystal composition with a smaller K / Δε ratio is of great significance for meeting the needs of low-power display applications.
[0006] In recent years, the development of high-refractive-index liquid crystal monomers, represented by thiophene structures, has become a hot topic in the liquid crystal materials industry. For example, the following thiophene derivatives are disclosed in patent application CN102325762B:
[0007] The following thiophene derivatives are disclosed in patent application CN116496794A:
[0008] These thiophene structures possess the excellent properties of both low rotational viscosity and high birefringence. However, with the iterative upgrades in display technology, the performance bottleneck of existing liquid crystal materials in terms of response speed is becoming increasingly prominent, necessitating the development of novel molecular structures with faster response speeds to meet the increasingly stringent demands of dynamic displays. Summary of the Invention
[0009] Therefore, the object of the present invention is to provide a liquid crystal composition and a liquid crystal display element and a liquid crystal display comprising the liquid crystal composition, so as to solve at least one of the above-mentioned technical problems. The liquid crystal composition of the present invention has a lower γ1 and a smaller γ1 / K. 11 and the smaller K 11 The absolute value of / Δε can be used to develop liquid crystal displays with fast response speed and low threshold voltage.
[0010] To achieve the above objectives, the present invention adopts the following technical solution: In a first aspect, the present invention provides a liquid crystal composition comprising: The first component is selected from one or more compounds shown in Formula I. Ⅰ Wherein, R1 and R2 independently represent a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein one or more non-adjacent -CH2- can be -C≡C-, -CH=CH-, -CF2O-, -OCF2-, -O-, -COO-, -OCO-, , , , or The O atoms are replaced in a manner that prevents them from being directly connected to each other, and one or more H atoms can be replaced by fluorine atoms; , Each represents independently or ; , Each represents independently , or One or more H atoms can be replaced by F atoms; L1 and L2 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein any one or more unconnected -CH2- can be replaced by -O-, -CO-, -CH2O-, -OCH2-, -COO-, or -OOC- in such a way that the O atoms are not directly connected to each other, and one or more H atoms can be replaced by a fluorine atom; n represents 0, 1, or 2; when n represents 2... Same or different; The second component is selected from one or more compounds shown in Formula II. II in, R3 and R4 represent alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, or alkenyl groups having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. , Each represents independently , , or ; a and b can each independently represent 1 or 2. When a represents 2, Same or different; b represents 2, Same or different; Z1 represents a single bond, -CH2-CH2, -CH2O-, -OCH2-, -COO-, -CH=CH-, or -C≡C-; and The third component is selected from one or more compounds in the group consisting of compounds shown in Formula III and compounds shown in Formula IV. III IV in, and Each represents independently , , , , or ; express , or ; R5 and R6 each independently represent an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropyl, cyclopentenyl, or cyclobutyl, and wherein one or more H atoms may be substituted with F. R7 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene, and wherein one or more H atoms may be substituted with F. R8 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. Z2 and Z3 independently represent single bonds, -CH2CH2-, -CH=CH-, -CH2O-, -OCH2-, -COO-, or -OCO-; W1 represents -O-, -S-, -Se-, -CH2O-, or -CH=CH-; c and d can each independently represent 0, 1, or 2; when c represents 2, Same or different; c indicates that Z2 is the same or different when it is 2; d indicates that when it is 2, They are either the same or different independently; x represents 0, 1, or 2. When x represents 2... Same or different; when x represents 2, Z3 is the same or different.
[0011] In a second aspect, the present invention provides a liquid crystal display element comprising the liquid crystal composition described in the first aspect above.
[0012] Thirdly, the present invention provides a liquid crystal display comprising the liquid crystal composition described in the first aspect above.
[0013] The beneficial effects of this invention are as follows: The liquid crystal composition provided by the present invention has a lower γ1 and a smaller γ1 / K. 11 and the smaller K 11 The absolute value of / Δε can be used to develop liquid crystal display elements and liquid crystal displays with fast response speed and low threshold voltage. Attached Figure Description
[0014] The specific embodiments of the present invention will be described in further detail below with reference to the accompanying drawings.
[0015] Figure 1 The MS mass spectrum of the organic compound represented by formula I-1-2-12 is shown.
[0016] Figure 2 The MS mass spectrum of the organic compound represented by formula I-1-3-12 is shown.
[0017] Figure 3 The MS mass spectrum of the organic compound represented by Formula I-1-4-2 is shown. Detailed Implementation
[0018] To more clearly illustrate the present invention, the following description, in conjunction with preferred embodiments and accompanying drawings, further explains the invention. Similar components in the drawings are indicated by the same reference numerals. Those skilled in the art should understand that the specific description below is illustrative rather than restrictive and should not be construed as limiting the scope of protection of the present invention.
[0019] According to a specific embodiment of the present invention, a liquid crystal composition is provided, the liquid crystal composition comprising: The first component is selected from one or more compounds shown in Formula I. Ⅰ Wherein, R1 and R2 independently represent a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein one or more non-adjacent -CH2- can be -C≡C-, -CH=CH-, -CF2O-, -OCF2-, -O-, -COO-, -OCO-, , , , or The O atoms are replaced in a manner that prevents them from being directly connected to each other, and one or more H atoms can be replaced by fluorine atoms; , Each represents independently or ; , Each represents independently , or One or more H atoms can be replaced by F atoms; L1 and L2 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein any one or more unconnected -CH2- can be replaced by -O-, -CO-, -CH2O-, -OCH2-, -COO-, or -OOC- in such a way that the O atoms are not directly connected to each other, and one or more H atoms can be replaced by a fluorine atom; n represents 0, 1, or 2; when n represents 2... Same or different; The second component is selected from one or more compounds shown in Formula II. II in, R3 and R4 represent alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, or alkenyl groups having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. , Each represents independently , , or ; a and b can each independently represent 1 or 2. When a represents 2, Same or different; b represents 2, Same or different; Z1 represents a single bond, -CH2-CH2, -CH2O-, -OCH2-, -COO-, -CH=CH-, or -C≡C-; and The third component is selected from one or more compounds in the group consisting of compounds shown in Formula III and compounds shown in Formula IV. III IV in, and Each represents independently , , , , or ; express , or ; R5 and R6 each independently represent an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropyl, cyclopentenyl, or cyclobutyl, and wherein one or more H atoms may be substituted with F. R7 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene, and wherein one or more H atoms may be substituted with F. R8 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. Z2 and Z3 independently represent single bonds, -CH2CH2-, -CH=CH-, -CH2O-, -OCH2-, -COO-, or -OCO-; W1 represents -O-, -S-, -Se-, -CH2O-, or -CH=CH-; c and d can each independently represent 0, 1, or 2; when c represents 2, Same or different; c indicates that Z2 is the same or different when it is 2; d indicates that when it is 2, They are either the same or different independently; x represents 0, 1, or 2. When x represents 2... Same or different; when x represents 2, Z3 is the same or different.
[0020] In some examples, L1 and L2 independently represent hydrogen atoms, fluorine atoms, alkyl groups having 1-6 carbon atoms, alkoxy groups having 1-6 carbon atoms, alkenyl groups having 2-6 carbon atoms, or alkenyloxy groups.
[0021] In some examples, the , Each represents independently , , , , , , , , , , or .
[0022] In some preferred examples, the express , , , , or , Each time it appears, it represents the same or different meanings. , , , , , or .
[0023] In some preferred examples, the express , or .
[0024] In some more preferred examples, the express or .
[0025] In some preferred examples, the Each time it appears, it represents the same or different meanings. , , or .
[0026] In some examples, the compound represented by Formula I is selected from the following compounds: Ⅰ-1 Ⅰ-2 Ⅰ-3 I-4 Ⅰ-5 Ⅰ-6 Ⅰ-7 I-8 Ⅰ-9 in, L 11 L 21 Each of the following can independently represent a fluorine atom, an alkyl group having 1-3 carbon atoms, an alkoxy group having 1-3 carbon atoms, or an alkenyl group having 2-3 carbon atoms, and one or more of the H atoms may be substituted by a fluorine atom; express , , , , or , Each time it appears, it represents the same or different meanings. , , , , , or
[0027] In some specific examples, the compound represented by Formula I-1 is selected from the compounds represented by Formulas I-1-1 to I-1-10. Ⅰ-1-1 Ⅰ-1-2 Ⅰ-1-3 Ⅰ-1-4 Ⅰ-1-5 Ⅰ-1-6 Ⅰ-1-7 Ⅰ-1-8 Ⅰ-1-9 Ⅰ-1-10; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0028] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0029] In some more specific examples, the compounds represented by Formula I-1-1 are selected from Formulas I-1-1-1 to I-1-1-11. Ⅰ-1-1-1 Ⅰ-1-1-2 Ⅰ-1-1-3 Ⅰ-1-1-4 Ⅰ-1-1-5 Ⅰ-1-1-6 Ⅰ-1-1-7 Ⅰ-1-1-8 Ⅰ-1-1-9 Ⅰ-1-1-10 Ⅰ-1-1-11.
[0030] In some more specific examples, the compounds represented by Formula I-1-2 are selected from Formulas I-1-2-1 to I-1-2-67. Ⅰ-1-2-1 Ⅰ-1-2-2 Ⅰ-1-2-3 Ⅰ-1-2-4 Ⅰ-1-2-5 Ⅰ-1-2-6 Ⅰ-1-2-7 Ⅰ-1-2-8 Ⅰ-1-2-9 Ⅰ-1-2-10 Ⅰ-1-2-11 Ⅰ-1-2-12 Ⅰ-1-2-13 Ⅰ-1-2-14 Ⅰ-1-2-15 Ⅰ-1-2-16 Ⅰ-1-2-17 Ⅰ-1-2-18 Ⅰ-1-2-19 Ⅰ-1-2-20 Ⅰ-1-2-21 Ⅰ-1-2-22 Ⅰ-1-2-23 Ⅰ-1-2-24 Ⅰ-1-2-25 Ⅰ-1-2-26 Ⅰ-1-2-27 Ⅰ-1-2-28 Ⅰ-1-2-29 Ⅰ-1-2-30 Ⅰ-1-2-31 Ⅰ-1-2-32 Ⅰ-1-2-33 Ⅰ-1-2-34 Ⅰ-1-2-35 Ⅰ-1-2-36 Ⅰ-1-2-37 Ⅰ-1-2-38 Ⅰ-1-2-39 Ⅰ-1-2-40 Ⅰ-1-2-41 Ⅰ-1-2-42 Ⅰ-1-2-43 Ⅰ-1-2-44 Ⅰ-1-2-45 Ⅰ-1-2-46 Ⅰ-1-2-47 Ⅰ-1-2-48 Ⅰ-1-2-49 Ⅰ-1-2-50 Ⅰ-1-2-51 Ⅰ-1-2-52 Ⅰ-1-2-53 Ⅰ-1-2-54 Ⅰ-1-2-55 Ⅰ-1-2-56 Ⅰ-1-2-57 Ⅰ-1-2-58 Ⅰ-1-2-59 Ⅰ-1-2-60 Ⅰ-1-2-61 Ⅰ-1-2-62 Ⅰ-1-2-63 Ⅰ-1-2-64 Ⅰ-1-2-65 Ⅰ-1-2-66 Ⅰ-1-2-67.
[0031] In some more specific examples, the compounds represented by Formula I-1-3 are selected from Formulas I-1-3-1 to I-1-3-68. Ⅰ-1-3-1 Ⅰ-1-3-2 Ⅰ-1-3-3 Ⅰ-1-3-4 Ⅰ-1-3-5 Ⅰ-1-3-6 Ⅰ-1-3-7 Ⅰ-1-3-8 Ⅰ-1-3-9 Ⅰ-1-3-10 Ⅰ-1-3-11 Ⅰ-1-3-12 Ⅰ-1-3-13 Ⅰ-1-3-14 Ⅰ-1-3-15 Ⅰ-1-3-16 Ⅰ-1-3-17 Ⅰ-1-3-18 Ⅰ-1-3-19 Ⅰ-1-3-20 Ⅰ-1-3-21 Ⅰ-1-3-22 Ⅰ-1-3-23 Ⅰ-1-3-24 Ⅰ-1-3-25 Ⅰ-1-3-26 Ⅰ-1-3-27 Ⅰ-1-3-28 Ⅰ-1-3-29 Ⅰ-1-3-30 Ⅰ-1-3-31 Ⅰ-1-3-32 Ⅰ-1-3-33 Ⅰ-1-3-34 Ⅰ-1-3-35 Ⅰ-1-3-36 Ⅰ-1-3-37 Ⅰ-1-3-38 Ⅰ-1-3-39 Ⅰ-1-3-40 Ⅰ-1-3-41 Ⅰ-1-3-42 Ⅰ-1-3-43 Ⅰ-1-3-44 Ⅰ-1-3-45 Ⅰ-1-3-46 Ⅰ-1-3-47 Ⅰ-1-3-48 Ⅰ-1-3-49 Ⅰ-1-3-50 Ⅰ-1-3-51 Ⅰ-1-3-52 Ⅰ-1-3-53 Ⅰ-1-3-54 Ⅰ-1-3-55 Ⅰ-1-3-56 Ⅰ-1-3-57 Ⅰ-1-3-58 Ⅰ-1-3-59 Ⅰ-1-3-60 Ⅰ-1-3-61 Ⅰ-1-3-62 Ⅰ-1-3-63 Ⅰ-1-3-64 Ⅰ-1-3-65 Ⅰ-1-3-66 Ⅰ-1-3-67 Ⅰ-1-3-68.
[0032] In some more specific examples, the compounds represented by Formula I-1-4 are selected from Formula I-1-4-1 to I-1-4-22. Ⅰ-1-4-1 Ⅰ-1-4-2 Ⅰ-1-4-3 Ⅰ-1-4-4 Ⅰ-1-4-5 Ⅰ-1-4-6 Ⅰ-1-4-7 Ⅰ-1-4-8 Ⅰ-1-4-9 Ⅰ-1-4-10 Ⅰ-1-4-11 Ⅰ-1-4-12 Ⅰ-1-4-13 Ⅰ-1-4-14 Ⅰ-1-4-15 Ⅰ-1-4-16 Ⅰ-1-4-17 Ⅰ-1-4-18 Ⅰ-1-4-19 Ⅰ-1-4-20 Ⅰ-1-4-21 Ⅰ-1-4-22.
[0033] In some more specific examples, the compounds represented by Formula I-1-5 are selected from Formulas I-1-5-1 to I-1-5-8. Ⅰ-1-5-1 Ⅰ-1-5-2 Ⅰ-1-5-3 Ⅰ-1-5-4 Ⅰ-1-5-5 Ⅰ-1-5-6 Ⅰ-1-5-7 Ⅰ-1-5-8.
[0034] In some more specific examples, the compounds represented by Formula I-1-6 are selected from Formulas I-1-6-1 to I-1-6-8. Ⅰ-1-6-1 Ⅰ-1-6-2 Ⅰ-1-6-3 Ⅰ-1-6-4 Ⅰ-1-6-5 Ⅰ-1-6-6 Ⅰ-1-6-7 Ⅰ-1-6-8.
[0035] In some more specific examples, the compounds represented by Formula I-1-8 are selected from Formulas I-1-8-1 to I-1-8-5. Ⅰ-1-8-1 Ⅰ-1-8-2 Ⅰ-1-8-3 Ⅰ-1-8-4 Ⅰ-1-8-5.
[0036] In some more specific examples, the compound represented by Formula I-1-9 is the compound represented by Formula I-1-9-1. Ⅰ-1-9-1.
[0037] In some more specific examples, the compound represented by Formula I-1-10 is the compound represented by Formula I-1-10-1. Ⅰ-1-10-1.
[0038] In some specific examples, the compound represented by formula I-2 is selected from the compounds represented by formulas I-2-1 to I-2-12. Ⅰ-2-1 Ⅰ-2-2 Ⅰ-2-3 Ⅰ-2-4 Ⅰ-2-5 Ⅰ-2-6 Ⅰ-2-7 Ⅰ-2-8 Ⅰ-2-9 Ⅰ-2-10 Ⅰ-2-11 Ⅰ-2-12; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0039] In some specific examples, R 11and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0040] In some more specific examples, the compounds represented by Formula I-2-2 are selected from Formulas I-2-2-1 to I-2-2-18. Ⅰ-2-2-1 Ⅰ-2-2-2 Ⅰ-2-2-3 Ⅰ-2-2-4 Ⅰ-2-2-5 Ⅰ-2-2-6 Ⅰ-2-2-7 Ⅰ-2-2-8 Ⅰ-2-2-9 Ⅰ-2-2-10 Ⅰ-2-2-11 Ⅰ-2-2-12 Ⅰ-2-2-13 Ⅰ-2-2-14 Ⅰ-2-2-15 Ⅰ-2-2-16 Ⅰ-2-2-17 Ⅰ-2-2-18.
[0041] In some more specific examples, the compounds represented by Formula I-2-4 are selected from Formulas I-2-4-1 to I-2-4-18. Ⅰ-2-4-1 Ⅰ-2-4-2 Ⅰ-2-4-3 Ⅰ-2-4-4 Ⅰ-2-4-5 Ⅰ-2-4-6 Ⅰ-2-4-7 Ⅰ-2-4-8 Ⅰ-2-4-9 Ⅰ-2-4-10 Ⅰ-2-4-11 Ⅰ-2-4-12 Ⅰ-2-4-13 Ⅰ-2-4-14 Ⅰ-2-4-15 Ⅰ-2-4-16 Ⅰ-2-4-17 Ⅰ-2-4-18.
[0042] In some more specific examples, the compounds represented by Formula I-2-5 are selected from Formulas I-2-5-1 to I-2-5-18. Ⅰ-2-5-1 Ⅰ-2-5-2 Ⅰ-2-5-3 Ⅰ-2-5-4 Ⅰ-2-5-5 Ⅰ-2-5-6 Ⅰ-2-5-7 Ⅰ-2-5-8 Ⅰ-2-5-9 Ⅰ-2-5-10 Ⅰ-2-5-11 Ⅰ-2-5-12 Ⅰ-2-5-13 Ⅰ-2-5-14 Ⅰ-2-5-15 Ⅰ-2-5-16 Ⅰ-2-5-17 Ⅰ-2-5-18.
[0043] In some more specific examples, the compounds represented by Formula I-2-6 are selected from Formulas I-2-6-1 to I-2-6-18. Ⅰ-2-6-1 Ⅰ-2-6-2 Ⅰ-2-6-3 Ⅰ-2-6-4 Ⅰ-2-6-5 Ⅰ-2-6-6 Ⅰ-2-6-7 Ⅰ-2-6-8 Ⅰ-2-6-9 Ⅰ-2-6-10 Ⅰ-2-6-11 Ⅰ-2-6-12 Ⅰ-2-6-13 Ⅰ-2-6-14 Ⅰ-2-6-15 Ⅰ-2-6-16 Ⅰ-2-6-17 Ⅰ-2-6-18.
[0044] In some specific examples, the compound represented by Formula I-3 is selected from the compounds represented by Formulas I-3-1 to I-3-8. Ⅰ-3-1 Ⅰ-3-2 Ⅰ-3-3、 Ⅰ-3-4 Ⅰ-3-5 Ⅰ-3-6 Ⅰ-3-7 Ⅰ-3-8; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0045] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0046] In some more specific examples, the compounds represented by Formula I-3-2 are selected from Formulas I-3-2-1 to I-3-2-12. Ⅰ-3-2-1 Ⅰ-3-2-2 Ⅰ-3-2-3 Ⅰ-3-2-4 Ⅰ-3-2-5 Ⅰ-3-2-6 Ⅰ-3-2-7 Ⅰ-3-2-8 Ⅰ-3-2-9 Ⅰ-3-2-10 Ⅰ-3-2-11 Ⅰ-3-2-12.
[0047] In some more specific examples, the compounds represented by Formula I-3-3 are selected from Formulas I-3-3-1 to I-3-3-12. Ⅰ-3-3-1 Ⅰ-3-3-2 Ⅰ-3-3-3 Ⅰ-3-3-4 Ⅰ-3-3-5 Ⅰ-3-3-6 Ⅰ-3-3-7 Ⅰ-3-3-8 Ⅰ-3-3-9 Ⅰ-3-3-10 Ⅰ-3-3-11 Ⅰ-3-3-12.
[0048] In some more specific examples, the compounds represented by Formula I-3-4 are selected from Formulas I-3-4-1 to I-3-4-10. Ⅰ-3-4-1 Ⅰ-3-4-2 Ⅰ-3-4-3 Ⅰ-3-4-4 Ⅰ-3-4-5 Ⅰ-3-4-6 Ⅰ-3-4-7 Ⅰ-3-4-8 Ⅰ-3-4-9 Ⅰ-3-4-10.
[0049] In some specific examples, the compound represented by Formula I-4 is selected from the compounds represented by Formulas I-4-1 to I-4-6. Ⅰ-4-1 Ⅰ-4-2 Ⅰ-4-3 Ⅰ-4-4 Ⅰ-4-5 Ⅰ-4-6; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0050] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0051] In some more specific examples, the compounds represented by Formula I-4-1 are selected from Formulas I-4-1-1 to I-4-1-10. Ⅰ-4-1-1 Ⅰ-4-1-2 Ⅰ-4-1-3 Ⅰ-4-1-4 Ⅰ-4-1-5 Ⅰ-4-1-6 Ⅰ-4-1-7 Ⅰ-4-1-8 Ⅰ-4-1-9 Ⅰ-4-1-10.
[0052] In some more specific examples, the compounds represented by Formula I-4-2 are selected from Formulas I-4-2-1 to I-4-2-10. Ⅰ-4-2-1 Ⅰ-4-2-2 Ⅰ-4-2-3 Ⅰ-4-2-4 Ⅰ-4-2-5 Ⅰ-4-2-6 Ⅰ-4-2-7 Ⅰ-4-2-8 Ⅰ-4-2-9 Ⅰ-4-2-10.
[0053] In some more specific examples, the compounds represented by Formula I-4-3 are selected from Formulas I-4-3-1 to I-4-3-10. Ⅰ-4-3-1 Ⅰ-4-3-2 Ⅰ-4-3-3 Ⅰ-4-3-4 Ⅰ-4-3-5 Ⅰ-4-3-6 Ⅰ-4-3-7 Ⅰ-4-3-8 Ⅰ-4-3-9 Ⅰ-4-3-10.
[0054] In some more specific examples, the compounds represented by Formula I-4-4 are selected from Formulas I-4-4-1 to I-4-4-10. Ⅰ-4-4-1 Ⅰ-4-4-2 Ⅰ-4-4-3 Ⅰ-4-4-4 Ⅰ-4-4-5 Ⅰ-4-4-6 Ⅰ-4-4-7 Ⅰ-4-4-8 Ⅰ-4-4-9 Ⅰ-4-4-10.
[0055] In some more specific examples, the compounds represented by Formula I-4-5 are selected from Formulas I-4-5-1 to I-4-5-10. Ⅰ-4-5-1 Ⅰ-4-5-2 Ⅰ-4-5-3 Ⅰ-4-5-4 Ⅰ-4-5-5 Ⅰ-4-5-6 Ⅰ-4-5-7 Ⅰ-4-5-8 Ⅰ-4-5-9 Ⅰ-4-5-10.
[0056] In some specific examples, the compound represented by Formula I-5 is selected from the compounds represented by Formulas I-5-1 to I-5-4. Ⅰ-5-1 Ⅰ-5-2 Ⅰ-5-3 Ⅰ-5-4; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0057] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0058] In some more specific examples, the compounds represented by Formula I-5-1 are selected from Formulas I-5-1-1 to I-5-1-12. Ⅰ-5-1-1 Ⅰ-5-1-2 Ⅰ-5-1-3 Ⅰ-5-1-4 Ⅰ-5-1-5 Ⅰ-5-1-6 Ⅰ-5-1-7 Ⅰ-5-1-8 Ⅰ-5-1-9 Ⅰ-5-1-10 Ⅰ-5-1-11 Ⅰ-5-1-12.
[0059] In some more specific examples, the compounds represented by Formula I-5-2 are selected from Formulas I-5-2-1 to I-5-2-12. Ⅰ-5-2-1 Ⅰ-5-2-2 Ⅰ-5-2-3 Ⅰ-5-2-4 Ⅰ-5-2-5 Ⅰ-5-2-6 Ⅰ-5-2-7 Ⅰ-5-2-8 Ⅰ-5-2-9 Ⅰ-5-2-10 Ⅰ-5-2-11 Ⅰ-5-2-12.
[0060] In some more specific examples, the compounds represented by Formula I-5-3 are selected from Formulas I-5-3-1 to I-5-3-12. Ⅰ-5-3-1 Ⅰ-5-3-2 Ⅰ-5-3-3 Ⅰ-5-3-4 Ⅰ-5-3-5 Ⅰ-5-3-6 Ⅰ-5-3-7 Ⅰ-5-3-8 Ⅰ-5-3-9 Ⅰ-5-3-10 Ⅰ-5-3-11 Ⅰ-5-3-12.
[0061] In some specific examples, the compound represented by Formula I-6 is selected from the compounds represented by Formulas I-6-1 to I-6-8. Ⅰ-6-1 Ⅰ-6-2 Ⅰ-6-3 Ⅰ-6-4 Ⅰ-6-5 Ⅰ-6-6 Ⅰ-6-7 Ⅰ-6-8; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0062] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0063] In some more specific examples, the compounds represented by Formula I-6-1 are selected from Formulas I-6-1-1 to I-6-1-4. Ⅰ-6-1-1 Ⅰ-6-1-2 Ⅰ-6-1-3 Ⅰ-6-1-4.
[0064] In some more specific examples, the compounds represented by Formula I-6-2 are selected from Formulas I-6-2-1 to I-6-2-4. Ⅰ-6-2-1 Ⅰ-6-2-2 Ⅰ-6-2-3 Ⅰ-6-2-4.
[0065] In some more specific examples, the compounds represented by Formula I-6-3 are selected from Formulas I-6-3-1 to I-6-3-4. Ⅰ-6-3-1 Ⅰ-6-3-2 Ⅰ-6-3-3 Ⅰ-6-3-4.
[0066] In some more specific examples, the compounds represented by Formula I-6-4 are selected from Formulas I-6-4-1 to I-6-4-4. Ⅰ-6-4-1 Ⅰ-6-4-2 Ⅰ-6-4-3 Ⅰ-6-4-4.
[0067] In some more specific examples, the compounds represented by Formula I-6-5 are selected from Formulas I-6-5-1 to I-6-5-4. Ⅰ-6-5-1 Ⅰ-6-5-2 Ⅰ-6-5-3 Ⅰ-6-5-4.
[0068] In some more specific examples, the compounds represented by Formula I-6-6 are selected from Formulas I-6-6-1 to I-6-6-4. Ⅰ-6-6-1 Ⅰ-6-6-2 Ⅰ-6-6-3 Ⅰ-6-6-4.
[0069] In some specific examples, the compound represented by formula I-7 is selected from the compounds represented by formulas I-7-1 to I-7-7. Ⅰ-7-1 Ⅰ-7-2 Ⅰ-7-3 Ⅰ-7-4 Ⅰ-7-5 Ⅰ-7-6 Ⅰ-7-7; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0070] In some specific examples, R 11and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0071] In some more specific examples, the compounds represented by Formula I-7-1 are selected from Formulas I-7-1-1 to I-7-1-4. Ⅰ-7-1-1 Ⅰ-7-1-2 Ⅰ-7-1-3 Ⅰ-7-1-4.
[0072] In some more specific examples, the compounds represented by Formula I-7-2 are selected from Formulas I-7-2-1 to I-7-2-4. Ⅰ-7-2-1 Ⅰ-7-2-2 Ⅰ-7-2-3 Ⅰ-7-2-4.
[0073] In some more specific examples, the compounds represented by Formula I-7-3 are selected from Formulas I-7-3-1 to I-7-3-4. Ⅰ-7-3-1 Ⅰ-7-3-2 Ⅰ-7-3-3 Ⅰ-7-3-4.
[0074] In some more specific examples, the compounds represented by Formula I-7-4 are selected from Formulas I-7-4-1 to I-7-4-4. Ⅰ-7-4-1 Ⅰ-7-4-2 Ⅰ-7-4-3 Ⅰ-7-4-4.
[0075] In some more specific examples, the compounds represented by Formula I-7-5 are selected from Formulas I-7-5-1 to I-7-5-4. Ⅰ-7-5-1 Ⅰ-7-5-2 Ⅰ-7-5-3 Ⅰ-7-5-4.
[0076] In some specific examples, the compound represented by formula I-8 is selected from the compounds represented by formulas I-8-1 to I-8-7. Ⅰ-8-1 Ⅰ-8-2 Ⅰ-8-3 Ⅰ-8-4 Ⅰ-8-5 Ⅰ-8-6 Ⅰ-8-7; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0077] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0078] In some more specific examples, the compounds represented by Formula I-8-1 are selected from Formulas I-8-1-1 to I-8-1-4. Ⅰ-8-1-1 Ⅰ-8-1-2 Ⅰ-8-1-3 Ⅰ-8-1-4.
[0079] In some more specific examples, the compounds represented by Formula I-8-2 are selected from Formulas I-8-2-1 to I-8-2-4. Ⅰ-8-2-1 Ⅰ-8-2-2 Ⅰ-8-2-3 Ⅰ-8-2-4.
[0080] In some more specific examples, the compounds represented by Formula I-8-3 are selected from Formulas I-8-3-1 to I-8-3-4. Ⅰ-8-3-1 Ⅰ-8-3-2 Ⅰ-8-3-3 Ⅰ-8-3-4.
[0081] In some more specific examples, the compounds represented by Formula I-8-4 are selected from Formulas I-8-4-1 to I-8-4-4. Ⅰ-8-4-1 Ⅰ-8-4-2 Ⅰ-8-4-3 Ⅰ-8-4-4.
[0082] In some more specific examples, the compounds represented by Formula I-8-5 are selected from Formulas I-8-5-1 to I-8-5-4. Ⅰ-8-5-1 Ⅰ-8-5-2 Ⅰ-8-5-3 Ⅰ-8-5-4.
[0083] In some specific examples, the compound represented by formula I-9 is selected from the compounds represented by formulas I-9-1 to I-9-2. Ⅰ-9-1 Ⅰ-9-2; The R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
[0084] In some specific examples, R 11 and R 21 Each of these terms independently represents an alkyl group having 1-5 carbon atoms, an alkoxy group having 1-5 carbon atoms, or an alkenyl group having 2-5 carbon atoms.
[0085] In some more specific examples, the compounds represented by Formula I-9-1 are selected from Formulas I-9-1-1 to I-9-1-4. Ⅰ-9-1-1 Ⅰ-9-1-2 Ⅰ-9-1-3 Ⅰ-9-1-4.
[0086] In some more specific examples, the compounds represented by Formula I-9-2 are selected from Formulas I-9-2-1 to I-9-2-4. Ⅰ-9-2-1 Ⅰ-9-2-2 Ⅰ-9-2-3 Ⅰ-9-2-4.
[0087] In some examples, the compounds of Formula I are selected from Formula I-1-2, I-1-3, I-1-4, I-1-5, I-2-2, I-2-3, I-2-4, I-2-5, I-2-6, I-2-7, I-3-2, I-3-3, I-3-4, I-3-5, I-4-1, I-4-2, I-4-3, I-4-4, I-4-5, I-4 -6、Ⅰ-5-1、Ⅰ-5-2、Ⅰ-5-3、Ⅰ-5-4、Ⅰ-6-1、Ⅰ-6-2、Ⅰ-6-3、Ⅰ-6-4、Ⅰ-6-5、Ⅰ-6-6、Ⅰ-7-1、Ⅰ-7-2、Ⅰ-7-3、Ⅰ-7-4、Ⅰ-7-5、Ⅰ-8-1、Ⅰ-8-2、Ⅰ-8-3、Ⅰ-8-4、Ⅰ-8-5、Ⅰ-9-1、Ⅰ-9-2、
[0088] In some preferred examples, the compound of formula I is selected from formulas I-1-2, I-1-3, I-1-4, I-1-5, I-2-2, I-2-4, I-2-6, I-2-7, I-3-2, I-3-3, I-3-4, I-3-5, I-4-1, I-4-3, I-4-5, I-4-6, I-5-1, I-5-2, I-5-3, I-5-4, I-6-1, I-6-2, I-6-3, I-7-1, I-7-2, I-7-3, I-8-1, I-8-2, I-8-3.
[0089] In some examples, the lower limit content of the compound represented by Formula I in the liquid crystal composition, by mass percentage, is selected from 1%, 2%, and 5%, and the upper limit content of the compound represented by Formula I is selected from 5%, 10%, 15%, 20%, 25%, 30%, and 40%.
[0090] In some specific examples, the content of the compound represented by Formula I in the liquid crystal composition, by mass percentage, includes but is not limited to 1-30%, 1-25%, 1-20%, 1-15%, 1-10%, 1-5%, 2-30%, 2-25%, 2-20%, 2-15%, 2-10%, 2-5%, 5-30%, 5-25%, 5-20%, 5-15%, 5-10%, 10-30%, 10-25%, 10-20%, 10-15%, 15-30%, 15-25%, 15-20%, 20-30%, 20-25%, 25-30%, etc.
[0091] In some examples, the compound represented by Formula II is selected from the group consisting of compounds represented by Formulas II-1 to II-18. II-1 II-2 II-3 II-4 II-5 II-6 II-7 II-8 II-9 II-10 II-11 II-12 II-13 II-14 II-15 II-16 II-17 II-18.
[0092] In some preferred embodiments, the compound represented by formula II-1 is selected from the compounds represented by formulas II-1-1 to II-1-9. II-1-1 Ⅱ-1-2 II-1-3 II-1-4 II-1-5 II-1-6 II-1-7 II-1-8 II-1-9; Among them, R 31 R 41 Each independently represents an alkyl chain with 1-10 carbon atoms, R 42 This refers to alkyl groups with 1-10 carbon atoms.
[0093] In some more preferred examples, the compound represented by formula II-1-1 is selected from the compounds represented by formulas II-1-1-1 to II-1-1-5. II-1-1-1 Ⅱ-1-1-2 II-1-1-3 II-1-1-4 Ⅱ-1-1-5.
[0094] In some more preferred examples, the compound represented by formula II-1-2 is selected from the compounds represented by formulas II-1-2-1 to II-1-2-5. Ⅱ-1-2-1 Ⅱ-1-2-2 II-1-2-3 II-1-2-4 Ⅱ-1-2-5.
[0095] In some more preferred examples, the compound represented by formula II-1-3 is selected from the compounds represented by formulas II-1-3-1 to II-1-3-4. II-1-3-1 Ⅱ-1-3-2 II-1-3-3 II-1-3-4.
[0096] In some more preferred examples, the compound represented by formula III-1-4 is selected from the compounds represented by formulas II-1-4-1 to II-1-4-4. II-1-4-1 Ⅱ-1-4-2 II-1-4-3 Ⅱ-1-4-4.
[0097] In some more preferred examples, the compound represented by formula II-1-5 is selected from the compounds represented by formulas II-1-5-1 to II-1-5-3. II-1-5-1 Ⅱ-1-5-2 Ⅱ-1-5-3.
[0098] In some more preferred examples, the compound represented by formula II-1-8 is selected from the compounds represented by formula II-1-8-1 and II-1-8-2. II-1-8-1 Ⅱ-1-8-2.
[0099] When a high response speed of the liquid crystal composition is required, it is preferable to use a higher content of the compound shown in formula II-1-3. When a high contrast ratio of the liquid crystal composition is required, it is preferable to use a higher content of the compounds shown in formula II-1-1, II-1-4, II-1-5, and II-1-8. When a high VHR of the liquid crystal composition is required, it is preferable to use a higher content of the compound shown in formula II-1-1.
[0100] More preferably, in the liquid crystal composition, the mass percentage of the compound shown in Formula II-1 is 1-80 wt%, the mass percentage of the compound shown in Formula II-1-1 is 0-15%, the mass percentage of the compound shown in Formula II-1-2 is 0-15%, the mass percentage of the compound shown in Formula II-1-3 is 1-60%, the mass percentage of the compound shown in Formula II-1-4 is 0-30%, the mass percentage of the compound shown in Formula II-1-5 is 0-12%, and the mass percentage of the compound shown in Formula II-1-8 is 0-12%.
[0101] Particularly preferably, in the liquid crystal composition, the mass percentage of the compound shown in Formula II-1 is 20-70 wt%, the mass percentage of the compound shown in Formula II-1-1 is 0-15%, the mass percentage of the compound shown in Formula II-1-2 is 0-8%, the mass percentage of the compound shown in Formula II-1-3 is 10-60%, and the mass percentage of the compound shown in Formula II-1-4 is 5-30%.
[0102] In some preferred examples, the compound represented by formula II-2 is selected from the compounds represented by formulas II-2-1 to II-2-7. II-2-1 Ⅱ-2-2 II-2-3 II-2-4 Ⅱ-2-5 Ⅱ-2-6 Ⅱ-2-7.
[0103] When high low-temperature solubility of the liquid crystal composition is required, it is preferable to use compounds with higher content of formulas II-2-1 and II-2-2. More preferably, the mass percentage of the compound represented by Formula II-2 in the liquid crystal composition is 0-20 wt%, particularly preferably 0-15%.
[0104] In some preferred embodiments, the compound represented by formula II-3 is selected from the compounds represented by formulas II-3-1 to II-3-3. II-3-1 Ⅱ-3-2 II-3-3.
[0105] Among them, R 31 R 41 Each independently represents an alkyl chain with 1-10 carbon atoms, R 42 This refers to alkyl groups with 1-10 carbon atoms.
[0106] In some preferred examples, formula II-3-1 is selected from the compounds shown in formulas II-3-1-1 to II-3-1-6. Ⅱ-3-1-1 Ⅱ-3-1-2 II-3-1-3 II-3-1-4 Ⅱ-3-1-5 Ⅱ-3-1-6.
[0107] In some preferred examples, formula II-3-2 is selected from the compounds shown in formulas II-3-2-1 to II-3-2-3. Ⅱ-3-2-1 Ⅱ-3-2-2 Ⅱ-3-2-3.
[0108] In some preferred examples, formula II-3-3 is selected from the compounds shown in formulas II-3-3-1 and II-3-3-2. II-3-3-1 Ⅱ-3-3-2.
[0109] In some preferred embodiments, the compound represented by formula II-4 is selected from the compounds represented by formulas II-4-1 to II-4-3. II-4-1 Ⅱ-4-2 II-4-3.
[0110] More preferably, the mass percentage of the compound represented by Formula II-4 in the liquid crystal composition is 0-20 wt%, particularly preferably 0-15%.
[0111] In some preferred embodiments, the compound represented by formula II-5 is selected from the compounds represented by formulas II-5-1 to II-5-5. II-5-1 II-5-2 II-5-3 II-5-4 II-5-5.
[0112] More preferably, the mass percentage of the compound shown in Formula II-5 in the liquid crystal composition is 0-10 wt%, particularly preferably 0-6%.
[0113] In some preferred embodiments, the compound represented by Formula II-6 is selected from the compounds represented by Formula II-6-1 to II-6-3. II-6-1 Ⅱ-6-2 Ⅱ-6-3.
[0114] Among them, R 31 R 41 Each independently represents an alkyl chain with 1-10 carbon atoms, R 32 It represents alkenyl groups with 2-10 carbon atoms.
[0115] In some preferred embodiments, the compound represented by formula II-6-1 is selected from the compounds represented by formulas II-6-1-1 to II-6-1-5. II-6-1-1 Ⅱ-6-1-2 Ⅱ-6-1-3 II-6-1-4 Ⅱ-6-1-5.
[0116] In some preferred embodiments, the compound represented by formula II-6-2 is selected from the compounds represented by formulas II-6-2-1 to II-6-2-6. II-6-2-1 Ⅱ-6-2-2 II-6-2-3 Ⅱ-6-2-4 Ⅱ-6-2-5 Ⅱ-6-2-6.
[0117] In some preferred examples, the compound represented by formula II-6-3 is selected from the compounds represented by formula II-6-3-1 and II-6-3-2. Ⅱ-6-3-1 Ⅱ-6-3-2.
[0118] More preferably, the mass percentage of the compound represented by Formula II-6 in the liquid crystal composition is 0-30 wt%.
[0119] In some preferred examples, the compound represented by formula II-7 is selected from the compounds represented by formulas II-7-1 to II-7-4. II-7-1 Ⅱ-7-2 II-7-3 II-7-4.
[0120] Among them, R 31 R 41 Each independently represents an alkyl chain with 1-10 carbon atoms, R 32 R represents an alkenyl group with 2-10 carbon atoms. 42 This refers to alkyl groups with 1-10 carbon atoms.
[0121] In some preferred examples, the compound represented by formula II-7-1 is selected from the compounds represented by formulas II-7-1-1 to II-7-1-6. II-7-1-1 Ⅱ-7-1-2 II-7-1-3 II-7-1-4 II-7-1-5 Ⅱ-7-1-6.
[0122] In some preferred examples, the compound represented by formula II-7-2 is selected from the compounds represented by formulas II-7-2-1 to II-7-2-6. II-7-2-1 Ⅱ-7-2-2 II-7-2-3 II-7-2-4 Ⅱ-7-2-5 Ⅱ-7-2-6.
[0123] In some preferred examples, the compound represented by formula II-7-3 is selected from the compounds represented by formulas II-7-3-1 to II-7-3-5. II-7-3-1 Ⅱ-7-3-2 II-7-3-3 II-7-3-4 Ⅱ-7-3-5.
[0124] In some preferred examples, the compound represented by formula II-7-4 is selected from the compounds represented by formula II-7-4-1 and II-7-4-2. II-7-4-1 Ⅱ-7-4-2.
[0125] When high contrast and response speed of the liquid crystal composition are required, it is preferable to use compounds with higher content of formulas II-7-1-1, II-7-1-2, II-7-1-4, II-7-3-1, and II-7-4-1.
[0126] In some examples, the liquid crystal composition contains 0-30 wt% of the compound represented by Formula II-7.
[0127] In some examples, the compound represented by formula II-8 is selected from the compounds represented by formulas II-8-1 to II-8-3. II-8-1 Ⅱ-8-2 II-8-3; Among them, R 31 R 41Each independently represents an alkyl chain with 1-10 carbon atoms, R 32 R represents an alkenyl group with 2-10 carbon atoms. 42 This refers to alkyl groups with 1-10 carbon atoms.
[0128] In some examples, the compound represented by formula II-8-1 is selected from the compounds represented by formulas II-8-1-1 to II-8-1-3. II-8-1-1 Ⅱ-8-1-2 Ⅱ-8-1-3.
[0129] In some examples, the compound represented by formula II-8-2 is selected from the compounds represented by formulas II-8-2-1 to II-8-2-4. II-8-2-1 Ⅱ-8-2-2 Ⅱ-8-2-3 Ⅱ-8-2-4.
[0130] In some examples, the compound represented by formula II-8-3 is selected from the compounds represented by formulas II-8-3-1 and II-8-3-2. II-8-3-1 Ⅱ-8-3-2.
[0131] Particularly preferably, the compound of formula II-8 is selected from one or more of the group consisting of formulas II-8-1-1, II-8-1-2, II-8-2-3, and II-8-3-2. More preferably, the mass percentage of the compound represented by Formula II-8 in the liquid crystal composition is 0-20 wt%.
[0132] In some examples, the compound represented by formula II-9 is selected from the compounds represented by formulas II-9-1 to II-9-5. Ⅱ-9-1 Ⅱ-9-2 Ⅱ-9-3 Ⅱ-9-4 Ⅱ-9-5.
[0133] More preferably, the mass percentage of the compound represented by Formula II-9 in the liquid crystal composition is 0-10 wt%.
[0134] In some examples, the compound represented by formula II-10 is selected from the compounds represented by formula II-10-1 and formula II-10-2. II-10-1 II-10-2; Among them, R 31 R 41 Each independently represents an alkyl chain with 1-10 carbon atoms, R 42 This refers to alkyl groups with 1-10 carbon atoms.
[0135] In some examples, the compound represented by formula II-10-1 is selected from the compounds represented by formula II-10-1-1 and formula II-10-1-6. Ⅱ-10-1-1 Ⅱ-10-1-2 Ⅱ-10-1-3 II-10-1-4 II-10-1-5 Ⅱ-10-1-6.
[0136] More preferably, the mass percentage of the compound represented by Formula II-10-1 in the liquid crystal composition is 0-20 wt%.
[0137] In some examples, the compound represented by formula II-10-2 is selected from the compounds represented by formula II-10-2-1 to II-10-2-3. Ⅱ-10-2-1 Ⅱ-10-2-2 Ⅱ-10-2-3.
[0138] More preferably, the mass percentage of the compound represented by Formula II-10-2 in the liquid crystal composition is 0-25 wt%.
[0139] In some examples, the compound represented by formula II-11 is selected from the compounds represented by formulas II-11-1 to II-11-6. II-11-1 Ⅱ-11-2 II-11-3 II-11-4 II-11-5 Ⅱ-11-6.
[0140] More preferably, the mass percentage of the compound represented by Formula II-11 in the liquid crystal composition is 0-8 wt%.
[0141] In some examples, the compound represented by formula II-12 is selected from the compounds represented by formulas II-12-1 to II-12-5. II-12-1 Ⅱ-12-2 II-12-3 II-12-4 II-12-5.
[0142] More preferably, the mass percentage of the compound represented by Formula II-12 in the liquid crystal composition is 0-8 wt%.
[0143] In some examples, the compound represented by formula II-13 is selected from the compounds represented by formulas II-13-1 to II-13-5. II-13-1 II-13-2 II-13-3 II-13-4 II-13-5.
[0144] More preferably, the mass percentage of the compound represented by Formula II-13 in the liquid crystal composition is 0-8 wt%.
[0145] In some examples, the compound represented by formula II-14 is selected from the compounds represented by formulas II-14-1 to II-14-5. II-14-1 II-14-2 II-14-3 II-14-4 II-14-5.
[0146] More preferably, the mass percentage of the compound represented by Formula II-14 in the liquid crystal composition is 0-8 wt%.
[0147] In some examples, the compound represented by formula II-15 is selected from the compounds represented by formulas II-15-1 to II-15-5. II-15-1 II-15-2 II-15-3 II-15-4 II-15-5.
[0148] More preferably, the mass percentage of the compound represented by Formula II-15 in the liquid crystal composition is 0-8 wt%.
[0149] In some examples, the compound represented by formula II-16 is selected from the compounds represented by formulas II-16-1 to II-16-4. II-16-1 II-16-2 II-16-3 II-16-4.
[0150] More preferably, the mass percentage of the compound represented by Formula II-16 in the liquid crystal composition is 0-8 wt%.
[0151] In some examples, the compound represented by formula II-17 is selected from the compounds represented by formulas II-17-1 to II-17-3. II-17-1 II-17-2 II-17-3.
[0152] More preferably, the mass percentage of the compound represented by Formula II-17 in the liquid crystal composition is 0-8 wt%.
[0153] In some examples, the compound represented by formula II-18 is selected from the compounds represented by formulas II-18-1 to II-18-4. II-18-1 Ⅱ-18-2 II-18-3 II-18-4.
[0154] More preferably, the mass percentage of the compound represented by Formula II-18 in the liquid crystal composition is 0-8 wt%.
[0155] In some examples, the lower limit content of the compound represented by Formula II in the liquid crystal composition, by mass percentage, is selected from 0, 1%, 5%, 10%, 20%, 30%, 40%, and the upper limit content of the compound represented by Formula II is selected from 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%.
[0156] In some specific examples, the content of the compound represented by Formula II in the liquid crystal composition, by mass percentage, includes, but is not limited to, 1-80%, 1-70%, 1-60%, 1-50%, 1-40%, 1-30%, 1-20%, 10-80%, 10-70%, 10-60%, 10-50%, 10-40%, 10-30%, 20-80%, 20-70%, 20-60%, 30-80%, 30-70%, 30-60%, 40-80%, 40-70%, 40-60%, 50-80%, 50-70%, etc.
[0157] In some examples, the compound represented by Formula III is selected from the group consisting of compounds represented by Formulas III-1 to III-18. Ⅲ-1 Ⅲ-2 Ⅲ-3 Ⅲ-4 Ⅲ-5 Ⅲ-6 Ⅲ-7 Ⅲ-8 Ⅲ-9 Ⅲ-10 Ⅲ-11 Ⅲ-12 Ⅲ-13 Ⅲ-14 Ⅲ-15 Ⅲ-16 Ⅲ-17 Ⅲ-18.
[0158] In some examples, the lower limit content of the compound represented by Formula III in the liquid crystal composition, by mass percentage, is selected from 0, 1%, 10%, 20%, 30%, 40%, 50%, and the upper limit content of the compound represented by Formula III is selected from 20%, 30%, 40%, 50%, 60%, 70%, 80%.
[0159] In some examples, the content of the compound represented by Formula III in the liquid crystal composition, by mass percentage, includes, but is not limited to, 0, 1-80%, 1-70%, 1-60%, 1-50%, 10-80%, 10-70%, 10-60%, 10-50%, 20-80%, 20-70%, 20-60%, 30-80%, 30-70%, 30-60%, etc.
[0160] In some examples, the compound represented by Formula IV is selected from the group consisting of compounds represented by Formulas IV-1 to IV-15. IV-1 IV-2 IV-3 IV-4 IV-5 IV-6 IV-7 IV-8 IV-9 IV-10 IV-11 IV-12 IV-13 IV-14 IV-15.
[0161] In some preferred examples, the compound represented by formula IV-1 is selected from the group consisting of compounds represented by formulas IV-1-1 to IV-1-4. IV-1-1 IV-1-2 IV-1-3 IV-1-4; Among them, R 71 R 81 Each independently represents an alkyl group having 1-10 carbon atoms, R 72 R 82 Each can be used independently to represent an olefinic group with 2-10 carbon atoms.
[0162] In some preferred examples, the compound represented by formula IV-1-1 is selected from formulas IV-1-1-1 to IV-1-1-6. IV-1-1-1 IV-1-1-2 IV-1-1-3 IV-1-1-4 IV-1-1-5 Ⅳ-1-1-6.
[0163] In some preferred examples, the compounds represented by formula IV-1-2 are selected from formulas IV-1-2-1 to IV-1-2-6. IV-1-2-1 IV-1-2-2 IV-1-2-3 IV-1-2-4 IV-1-2-5 Ⅳ-1-2-6.
[0164] In some preferred examples, the compounds represented by formula IV-1-3 are selected from formulas IV-1-3-1 to IV-1-3-12. IV-1-3-1 IV-1-3-2 IV-1-3-3 IV-1-3-4 IV-1-3-5 IV-1-3-6 IV-1-3-7 IV-1-3-8 IV-1-3-9 IV-1-3-10 IV-1-3-11 Ⅳ-1-3-12.
[0165] In some preferred examples, the compounds represented by formula IV-1-4 are selected from formulas IV-1-4-1 and IV-1-4-2. IV-1-4-1 Ⅳ-1-4-2.
[0166] In some preferred examples, the compound represented by formula IV-2 is selected from formulas IV-2-1 and IV-2-4. IV-2-1 IV-2-2 IV-2-3 Ⅳ-2-4.
[0167] In some preferred examples, the compound represented by formula IV-9 is selected from formulas IV-9-1 to IV-9-5. IV-9-1 IV-9-2 IV-9-3 IV-9-4 Ⅳ-9-5.
[0168] Preferably, based on mass percentage, the lower limit content of the compound represented by Formula IV in the liquid crystal composition is selected from 0, 1%, 3%, 5%, and 10%, and the upper limit content of the compound represented by Formula IV is selected from 5%, 10%, 15%, 20%, 25%, and 30%.
[0169] More preferably, based on mass percentage, the content of the compound represented by Formula IV in the liquid crystal composition includes, but is not limited to, 0, 1-30%, 1-25%, 1-20%, 1-10%, 3-30%, 3-25%, 3-20%, 3-10%, 5-30%, 5-25%, 5-20%, 5-10%, 10-20%, 10-25%, 10-30%, etc.
[0170] In some examples, the liquid crystal composition comprises, by weight percentage: 1-30% of the first component, 1-80% of the second component, and 1-80% of the third component.
[0171] In some preferred examples, the liquid crystal composition comprises, by weight percentage: 1) 1-30% of the compound shown in Formula I; 2) 1-80% of the compound shown in Formula II; and 3) 1-80% of the compound shown in Formula III or 1-30% of the compound shown in Formula IV.
[0172] In some more preferred examples, the liquid crystal composition comprises, by weight percentage: 1) 1-20% of the compound shown in Formula I; 2) 20-70% of the compound shown in Formula II; and 3) 10-70% of the compound shown in Formula III or 1-20% of the compound shown in Formula IV.
[0173] In some examples, the liquid crystal composition further comprises one or more compounds of formula V. V in, and Each represents independently , , , , or ; R9 represents an alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropyl, cyclopentyl, or cyclobutyl, and any one or more hydrogen atoms may optionally be substituted with fluorine atoms. R 10 R 11 Each of the following can independently represent H, F, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein any one or more hydrogen atoms may be optionally substituted with fluorine atoms; W2 represents -O- or -S-.
[0174] In some examples, the compound represented by formula V is selected from the group consisting of compounds represented by formulas V-1 to V-24 below. V-1 V-2 V-3 V-4 V-5 V-6 V-7 V-8 V-9 V-10 V-11 V-12 V-13 V-14 V-15 V-16 V-17 V-18 V-19 V-20 V-21 V-22 V-23 V-24.
[0175] Preferably, based on mass percentage, the lower limit content of the compound represented by Formula V in the liquid crystal composition is selected from 0, 1%, 2%, and 5%, and the upper limit content of the compound represented by Formula V is selected from 5%, 10%, 15%, and 20%.
[0176] In some specific examples, the content of the compound represented by formula V in the liquid crystal composition, by mass percentage, includes, but is not limited to, 0%, 1-20%, 1-15%, 1-10%, 1-5%, etc.
[0177] Preferably, the liquid crystal display device is an IPS or FFS mode display.
[0178] Various functional additives may be added to the liquid crystal composition provided in this embodiment, wherein the mass percentage of each additive is relative to the total mass of all liquid crystal compounds excluding the additives. The mass percentage of exemplary additives is preferably between 0.01-2 wt%. These additives are mainly chiral agents, antioxidants, light stabilizers, polymerizable monomers, self-aligning agents, etc.
[0179] Exemplary antioxidant and light stabilizer additives are selected from the following compounds:
[0180]
[0181] Exemplary polymerizable monomer additives are selected from the following compounds:
[0182]
[0183] .
[0184] According to yet another embodiment of the present invention, a liquid crystal display element is provided, comprising the liquid crystal composition described in the first embodiment above.
[0185] According to yet another embodiment of the present invention, a liquid crystal display is provided, comprising the liquid crystal composition described in the first embodiment above.
[0186] Example The technical solution of the present invention will be described below with reference to some specific embodiments.
[0187] In this invention, the preparation methods are all conventional unless otherwise specified, and the raw materials used can be obtained from publicly available commercial sources unless otherwise specified. The reaction process is generally monitored by TLC. The post-reaction treatment generally includes water washing, extraction, drying after combining organic phases, solvent removal under reduced pressure, recrystallization, and column chromatography. Those skilled in the art can implement this invention according to the following description.
[0188] All percentages in this instruction manual refer to mass percentages, and temperatures are in degrees Celsius (°C). The specific meanings of other symbols and test conditions are as follows: Tni represents the liquid crystal clearing point (°C), measured by DSC quantitative method; Δn represents optical anisotropy, Δn = n e -n o , where n o Let n be the refractive index of ordinary light. e The refractive index of unusual light was measured at 25±2℃, 589nm, using an Abbe refractometer. Δε represents dielectric anisotropy, Δε = ε ∥ -ε ⊥ , where ε ∥ ε is the dielectric constant parallel to the molecular axis. ⊥ The dielectric constant is perpendicular to the molecular axis. The test conditions are 25±0.5℃, 20-micron vertical or parallel cell, and INSTEC:ALCT-IR1 test. γ1 represents rotational viscosity (mPa·s), and the test conditions are 25±0.5℃, 20-micron vertical or parallel cell, INSTEC:ALCT-IR1 test; K 11 K is the elastic constant of the development. 33 The bending elastic constant is determined by the following test conditions: 25℃, INSTEC:ALCT-IR1, and a 20-micron vertical or parallel box. The preparation method of the liquid crystal composition is as follows: Weigh each liquid crystal monomer according to a certain ratio and put it into a stainless steel beaker. Place the stainless steel beaker containing each liquid crystal monomer on a magnetic stirrer and heat it to melt. After most of the liquid crystal monomer in the stainless steel beaker has melted, add a magnetic rotor to the stainless steel beaker and stir the mixture evenly. After cooling to room temperature, the liquid crystal composition is obtained.
[0189] The liquid crystal monomer structure in the embodiments of the present invention is represented by codes. The code representation methods for liquid crystal ring structure, end groups, and linking groups are shown in Tables 1 and 2 below.
[0190] Table 1. Corresponding codes for ring structures
[0191] Table 2. Correspondence codes between terminal groups and linking groups
[0192] For example: Its code is COY-3-O2; Its code is PP-5-3; Its code is CY-3-O2; Its code is CC-Cp-V1; Its code is PGP-Cpr1-2; Its code is PGBf-3-5F,6F; Its code is ThG[~F]Th-2-2; Its code is ThUTh-3-1[~1]; Its code is Sc-2O-O2(1)V.
[0193] In this embodiment, the compounds and intermediates of Formula I and its sub-formulas can be prepared in a manner similar to those known to those skilled in the art and described in standard works of organic chemistry (e.g., in Houben-Weyl, Methods of Organic Chemistry, Thieme-Verlag, Stuttgart).
[0194] The compound shown in Formula I mentioned in this embodiment is obtained by selectively brominating thiophene boric acid with fluorine-substituted p-chlorobromobenzene under palladium-containing catalyst conditions to obtain a chlorinated intermediate, which is then coupled with the corresponding thiophene boric acid compound under palladium-containing catalyst conditions to obtain the compound shown in Formula I.
[0195] Synthesis Example 1 This embodiment provides a liquid crystal compound I-1-2-12, the structure of which and its synthetic route are as follows: Ⅰ-1-2-12
[0196] Step 1: In a three-necked flask, 18.5 g (0.088 mol) of 2-fluoro-4-bromochlorobenzene, 15 g (0.088 mol) of 5-propylthiophene-2-boronic acid, 11.2 g (0.106 mol) of anhydrous sodium carbonate, 200 mL of tetrahydrofuran, and 60 mL of water were added sequentially. The mixture was stirred thoroughly and purged with nitrogen three times. Then, tetra(triphenylphosphine)palladium (0.51 g, 0.44 mmol) was added, and the mixture was refluxed for 12 hours. After the reaction was complete, 200 mL of water was added and stirred thoroughly. The mixture was extracted with 3 × 150 mL of ethyl acetate, and the organic layers were combined. The organic layers were washed with 200 mL of water and 100 mL of saturated brine. The organic layers were dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain crude intermediate 1. The crude product was recrystallized from 3 times the amount of ethanol and filtered under vacuum at -20 °C to obtain white solid intermediate 1 (18 g, 0.071 mol).
[0197] Step 2: In a three-necked flask, intermediate 1 (18 g, 0.071 mol), 5-ethylthiophene-2-boronic acid (11.1 g, 0.071 mol), anhydrous sodium carbonate (9 g, 0.085 mol), 180 mL tetrahydrofuran, and 60 mL water were added sequentially. The mixture was stirred thoroughly and purged with nitrogen three times. Then, Sphos Pd-G2 catalyst (0.05 g, 0.071 mmol) was added, and the mixture was refluxed for 8 hours. After the reaction was complete, 200 mL of water was added and stirred thoroughly. The mixture was extracted with 3 × 150 mL ethyl acetate, and the organic layers were combined. The organic layers were washed with 200 mL of water and 100 mL of saturated brine. The organic layers were dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain the crude product. The crude product was recrystallized four times with 1 part toluene and 2 parts ethanol to obtain a white solid I-1-2-12 (13.5 g) with a GC purity of 99.91%.
[0198] The mass spectrum of compound I-1-2-12 is as follows Figure 1 As shown.
[0199] Synthesis Example 2 This embodiment provides a liquid crystal compound I-1-3-11, the structure of which and its synthetic route are as follows: Ⅰ-1-3-11
[0200] Step 1: In a three-necked flask, 30 g (0.132 mol) of 2,6-difluoro-4-bromochlorobenzene, 22.4 g (0.132 mol) of 5-propylthiophene-2-boric acid, 16.7 g (0.158 mol) of anhydrous sodium carbonate, 200 mL of tetrahydrofuran, and 70 mL of water were added sequentially. The mixture was stirred thoroughly and purged with nitrogen three times. Then, tetra(triphenylphosphine)palladium (0.76 g, 0.66 mmol) was added, and the mixture was refluxed for 12 hours. After the reaction was complete, 200 mL of water was added and stirred thoroughly. The mixture was extracted with 3 × 150 mL of ethyl acetate, and the organic layers were combined. The organic layers were washed with 200 mL of water and 100 mL of saturated brine. The organic layers were dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain crude intermediate 1. The crude product was recrystallized from 3 times the amount of ethanol to obtain white solid intermediate 1 (28 g, 0.103 mol).
[0201] Step 2: In a three-necked flask, intermediate 1 (10 g, 0.037 mol), 5-methylthiophene-2-boric acid (5.3 g, 0.037 mol), anhydrous sodium carbonate (4.7 g, 0.044 mol), 100 mL tetrahydrofuran, and 35 mL water were added sequentially. The mixture was stirred thoroughly and purged with nitrogen three times. Then, Sphos Pd-G2 catalyst (0.03 g, 0.037 mmol) was added, and the mixture was refluxed for 8 hours. After the reaction was complete, 150 mL of water was added and stirred thoroughly. The mixture was extracted with 3 × 100 mL ethyl acetate, and the organic layers were combined. The organic layers were washed with 100 mL of water and 100 mL of saturated brine. The organic layers were dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain the crude product. The crude product was recrystallized twice with 1 part n-heptane and 3 parts ethanol to obtain a white solid I1-3-11 (6.5 g) with a GC purity of 99.93%.
[0202] Following the preparation method of compound I-1-3-11, compound I-1-3-12 was prepared by simply replacing the raw materials.
[0203] The mass spectrum of compound I-1-3-12 is as follows: Figure 2 As shown.
[0204] Synthesis Example 3 This embodiment provides a liquid crystal compound I-1-4-2, the structure of which and its synthetic route are as follows: Ⅰ-1-4-2
[0205] In a three-necked flask, 1,4-dibromo-2,3-difluorobenzene (10 g, 0.037 mol), 5-ethylthiophene-2-boric acid (12.2 g, 0.078 mol), anhydrous sodium carbonate (9.4 g, 0.089 mol), 100 mL tetrahydrofuran, and 30 mL water were added sequentially. The mixture was stirred thoroughly and purged with nitrogen three times. Then, tetra(triphenylphosphine)palladium catalyst (0.43 g, 0.37 mmol) was added, and the mixture was refluxed for 8 hours. After the reaction was complete, 100 mL of water was added and the mixture was stirred thoroughly. The mixture was extracted with 3 × 100 mL ethyl acetate, and the organic layers were combined. The organic layers were washed with 200 mL of water and 100 mL of saturated brine. The organic layers were dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain the crude product. The crude product was recrystallized three times with 1 part toluene and 2 parts ethanol to obtain a white solid I-1-4-2 (8.6 g) with a GC purity of 99.85%.
[0206] The mass spectrum of compound I-1-4-2 is as follows Figure 3 As shown.
[0207] It should be noted that in the examples and comparative examples of the liquid crystal compositions below, the content of the compounds shown in Formulas I to XI is based on the total mass of the compounds shown in Formulas I to V; the content of the compounds shown in Formula T and Formula RM is based on the total amount of the compounds shown in Formulas I to V.
[0208] Example 1 The formulation and physical properties of the liquid crystal composition in Example 1 are shown in Table 3 below.
[0209] Table 3 Formulation and physical properties of the liquid crystal composition in Example 1
[0210] Example 2 The formulation and physical properties of the liquid crystal composition in Example 2 are shown in Table 4 below.
[0211] Table 4 Formulation and physical properties of the liquid crystal composition in Example 2
[0212] Example 3 The formulation and physical properties of the liquid crystal composition in Example 3 are shown in Table 5 below.
[0213] Table 5 Formulation and physical properties of the liquid crystal composition in Example 3
[0214] Example 4 The formulation and physical properties of the liquid crystal composition in Example 4 are shown in Table 6 below.
[0215] Table 6 Formulation and physical properties of the liquid crystal composition in Example 4
[0216] Example 5 The formulation and physical properties of the liquid crystal composition in Example 5 are shown in Table 7 below.
[0217] Table 7 Formulation and physical properties of the liquid crystal composition in Example 5
[0218] Example 6 The formulation and physical properties of the liquid crystal composition in Example 6 are shown in Table 8 below.
[0219] Table 8 Formulation and physical properties of the liquid crystal composition in Example 6
[0220] Example 7 The formulation and physical properties of the liquid crystal composition in Example 7 are shown in Table 9 below.
[0221] Table 9 Formulation and physical properties of the liquid crystal composition in Example 7
[0222] Example 8 The formulation and physical properties of the liquid crystal composition in Example 8 are shown in Table 10 below.
[0223] Table 10 Formulation and physical properties of the liquid crystal composition in Example 8
[0224] Example 9 The formulation and physical properties of the liquid crystal composition in Example 9 are shown in Table 11 below.
[0225] Table 11 Formulation and physical properties of the liquid crystal composition in Example 9
[0226] Example 10 The formulation and physical properties of the liquid crystal composition in Example 10 are shown in Table 12 below.
[0227] Table 12 Formulation and physical properties of the liquid crystal composition in Example 10
[0228] Example 11 The formulation and physical properties of the liquid crystal composition in Example 11 are shown in Table 13 below.
[0229] Table 13 Formulation and physical properties of the liquid crystal composition in Example 11
[0230] Example 12 The formulation and physical properties of the liquid crystal composition in Example 12 are shown in Table 14 below.
[0231] Table 14 Formulation and physical properties of the liquid crystal composition in Example 12
[0232] Example 13 The formulation and physical properties of the liquid crystal composition in Example 13 are shown in Table 15 below.
[0233] Table 15 Formulation and physical properties of the liquid crystal composition in Example 13
[0234] Example 14 The formulation and physical properties of the liquid crystal composition in Example 14 are shown in Table 16 below.
[0235] Table 16 Formulation and physical properties of the liquid crystal composition in Example 14
[0236] Example 15 The formulation and physical properties of the liquid crystal composition in Example 15 are shown in Table 17 below.
[0237] Table 17 Formulation and physical properties of the liquid crystal composition in Example 15
[0238] Comparative Example 1 The formulation and physical properties of the liquid crystal composition of Comparative Example 1 are shown in Table 18 below.
[0239] Table 18 Comparative Example 1 Liquid Crystal Composition Formulation and Physical Properties
[0240] Comparative Example 2 The formulation and physical properties of the liquid crystal composition of Comparative Example 2 are shown in Table 19 below.
[0241] Table 19 Comparative Example 2: Liquid Crystal Composition Formulation and Physical Properties
[0242] By comparing Examples 1-15 with Comparative Examples 1-2, it can be seen that the technical solution disclosed in this invention has a lower γ1 and a smaller γ1 / K. 11 and the smaller K 11 / Δε absolute value.
[0243] By comparing Example 12 with Comparative Examples 1 and 2, it can be seen that, compared with the prior art, the technical solution disclosed in this invention has a lower γ1 value and a smaller γ1 / K. 11 and the smaller K 11 / Δε absolute value. Therefore, the display prepared from the liquid crystal composition shown in Example 12 has a faster response speed and a lower threshold voltage.
[0244] By comparing K in Example 14 and Example 15 11 Based on the absolute value of / Δε, the liquid crystal composition containing I-1-4-3 has a smaller K value than the liquid crystal composition containing I-1-3-12. 11 / Δε absolute value. This is because, express When the compound shown in Formula I exhibits negative dielectric anisotropy in the negative composition, therefore when express When the compound shown in Formula I has a smaller K, 11 The absolute value of / Δε results in a liquid crystal display with a lower threshold voltage.
[0245] Obviously, the above embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the implementation of the present invention. For those skilled in the art, other variations or modifications can be made based on the above description. It is impossible to exhaustively list all the implementation methods here. All obvious variations or modifications derived from the technical solutions of the present invention are still within the protection scope of the present invention.
Claims
1. A liquid crystal composition, characterized in that, The liquid crystal composition contains: The first component is selected from one or more compounds shown in Formula I. Ⅰ Wherein, R1 and R2 independently represent a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein one or more non-adjacent -CH2- can be -C≡C-, -CH=CH-, -CF2O-, -OCF2-, -O-, -COO-, -OCO-, , , , or The O atoms are replaced in a manner that prevents them from being directly connected to each other, and one or more H atoms can be replaced by fluorine atoms; , Each represents independently or ; , Each represents independently , or One or more H atoms can be replaced by F atoms; L1 and L2 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl or alkenoxy group having 2-10 carbon atoms, wherein any one or more unconnected -CH2- can be replaced by -O-, -CO-, -CH2O-, -OCH2-, -COO-, or -OOC- in such a way that the O atoms are not directly connected to each other, and one or more H atoms can be replaced by a fluorine atom; n represents 0, 1, or 2; when n represents 2... Same or different; The second component is selected from one or more compounds shown in Formula II. Ⅱ in, R3 and R4 represent alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, or alkenyl groups having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. , Each represents independently , , or ; a and b can each independently represent 1 or 2. When a represents 2, Same or different; b represents 2, Same or different; Z1 represents a single bond, -CH2-CH2, -CH2O-, -OCH2-, -COO-, -CH=CH-, or -C≡C-; and The third component is selected from one or more compounds in the group consisting of compounds shown in Formula III and compounds shown in Formula IV. Ⅲ Ⅳ in, and Each represents independently , , , , or ; express , or ; R5 and R6 each independently represent an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropyl, cyclopentenyl, or cyclobutyl, and wherein one or more H atoms may be substituted with F. R7 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- atoms may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene, and wherein one or more H atoms may be substituted with F. R8 represents an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropylene, cyclopentylene, cyclopentenylene, or cyclobutylene. Z2 and Z3 independently represent single bonds, -CH2CH2-, -CH=CH-, -CH2O-, -OCH2-, -COO-, or -OCO-; W1 represents -O-, -S-, -Se-, -CH2O-, or -CH=CH-; c and d can each independently represent 0, 1, or 2; when c represents 2, Same or different; c indicates that Z2 is the same or different when it is 2; d indicates that when it is 2, They are either the same or different independently; x represents 0, 1, or 2. When x represents 2... Same or different; when x represents 2, Z3 is the same or different.
2. The liquid crystal composition according to claim 1, characterized in that, L1 and L2 independently represent hydrogen atoms, fluorine atoms, alkyl groups with 1-6 carbon atoms, alkoxy groups with 1-6 carbon atoms, alkenyl or alkenoxy groups with 2-6 carbon atoms; and / or , Each represents independently , , , , , , , or .
3. The liquid crystal composition according to claim 1, characterized in that, The compound represented by Formula I is selected from the following compounds: Ⅰ-1 Ⅰ-2 Ⅰ-3 Ⅰ-4 Ⅰ-5 Ⅰ-6 Ⅰ-7 Ⅰ-8 Ⅰ-9 in, L 11 L 21 Each of the following can independently represent a fluorine atom, an alkyl group having 1-3 carbon atoms, an alkoxy group having 1-3 carbon atoms, or an alkenyl group having 2-3 carbon atoms, and one or more of the H atoms may be substituted by a fluorine atom; express , , , , or , Each occurrence represents the same or different meanings. , , , , , or .
4. The liquid crystal composition according to claim 3, characterized in that, The compound represented by Formula I is selected from the following compounds: Ⅰ-1-2 Ⅰ-1-3 Ⅰ-1-4 Ⅰ-1-5 Ⅰ-2-2 Ⅰ-2-3 Ⅰ-2-4 Ⅰ-2-5 Ⅰ-2-6 Ⅰ-2-7 Ⅰ-3-2 Ⅰ-3-3 Ⅰ-3-4 Ⅰ-3-5 Ⅰ-4-1 Ⅰ-4-2 Ⅰ-4-3 Ⅰ-4-4 Ⅰ-4-5 Ⅰ-4-6 Ⅰ-5-1 Ⅰ-5-2 Ⅰ-5-3 Ⅰ-5-4 Ⅰ-6-1 Ⅰ-6-2 Ⅰ-6-3 Ⅰ-6-4 Ⅰ-6-5 Ⅰ-6-6 Ⅰ-7-1 Ⅰ-7-2 Ⅰ-7-3 Ⅰ-7-4 Ⅰ-7-5 Ⅰ-8-1 Ⅰ-8-2 Ⅰ-8-3 Ⅰ-8-4 Ⅰ-8-5 Ⅰ-9-1 Ⅰ-9-2 in, R 11 and R 21 Each of these groups independently represents a fluorine atom, an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, or an alkenyl group having 2-6 carbon atoms, wherein one or more non-adjacent -CH2- groups can be... , , , or Substitution, and one or more of the H atoms can be substituted by fluorine atoms.
5. The liquid crystal composition according to claim 1, characterized in that, The liquid crystal composition comprises, by weight percentage: 1-30% of the first component, 1-80% of the second component, and 1-80% of the third component.
6. The liquid crystal composition according to claim 1, characterized in that, It also includes one or more compounds of formula V: Ⅴ in, and Each represents independently , , , , or ; R9 represents an alkyl group having 1-10 carbon atoms, an alkenyl group having 2-10 carbon atoms, or an alkoxy group having 1-10 carbon atoms, wherein one or more unconnected -CH2- groups may optionally be substituted with cyclopropyl, cyclopentyl, or cyclobutyl, and any one or more hydrogen atoms may optionally be substituted with fluorine atoms. R 10 R 11 Each of the following can independently represent H, F, an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkenyl group having 2-10 carbon atoms, wherein any one or more hydrogen atoms may be optionally substituted with fluorine atoms; W2 represents -O- or -S-.
7. The liquid crystal composition according to claim 1, characterized in that, The compound represented by Formula II is selected from the group consisting of compounds represented by Formulas II-1 to II-18. Ⅱ-1 Ⅱ-2 Ⅱ-3 Ⅱ-4 Ⅱ-5 Ⅱ-6 Ⅱ-7 Ⅱ-8 Ⅱ-9 Ⅱ-10 Ⅱ-11 Ⅱ-12 Ⅱ-13 Ⅱ-14 Ⅱ-15 Ⅱ-16 Ⅱ-17 Ⅱ-18。 8. The liquid crystal composition according to claim 1, characterized in that, The compound represented by Formula III is selected from the group consisting of compounds represented by Formulas III-1 to III-18: Ⅲ-1 Ⅲ-2 Ⅲ-3 Ⅲ-4 Ⅲ-5 Ⅲ-6 Ⅲ-7 Ⅲ-8 Ⅲ-9 Ⅲ-10 Ⅲ-11 Ⅲ-12 Ⅲ-13 Ⅲ-14 Ⅲ-15 Ⅲ-16 Ⅲ-17 Ⅲ-18。 9. The liquid crystal composition according to claim 1, characterized in that, The compound represented by Formula IV is selected from the group consisting of compounds represented by Formulas IV-1 to IV-15: Ⅳ-1 Ⅳ-2 Ⅳ-3 Ⅳ-4 Ⅳ-5 Ⅳ-6 Ⅳ-7 Ⅳ-8 Ⅳ-9 Ⅳ-10 Ⅳ-11 Ⅳ-12 Ⅳ-13 Ⅳ-14 Ⅳ-15。 10. A liquid crystal display element, characterized in that, It comprises the liquid crystal composition as described in any one of claims 1-9.
11. A liquid crystal display, characterized in that, It comprises the liquid crystal composition as described in any one of claims 1-9.
Citation Information
Patent Citations
Thiophene derivates and liquid crystal media comprising the same
CN102325762B
Liquid crystal compound containing thiophene, liquid crystal composition containing liquid crystal compound and liquid crystal display device
CN116496794A