An isothiocyanate liquid crystal compound, a liquid crystal composition comprising the same, and a high-frequency component

Abstract

The application relates to the technical field of liquid crystal materials, and particularly discloses an isothiocyanate liquid crystal compound, a liquid crystal composition containing the same and a high-frequency component. The liquid crystal compound is a compound shown in the following formula I, wherein Q1 represents O, S or Se. The liquid crystal compound provided by the application contains a benzofuran, benzothiophene or benzoselenophene structure in the main ring of the molecular structure, the liquid crystal compound with the specific structure has a higher clearing point, a lower dielectric loss, a higher dielectric tuning rate tau and a higher quality factor eta. The liquid crystal composition containing the organic compound also has a higher clearing point, a lower dielectric loss, a higher dielectric tuning rate tau and a higher quality factor eta, and can be used for developing components and devices with high-frequency technology applied in the microwave range, in particular, microwave phase-shifting devices, tunable filters, tunable metamaterial structures and electronic beam steering antennas.

Description

Technical Field

[0001] This invention relates to the field of liquid crystal materials technology, and more particularly to an isothiocyanate liquid crystal compound, as well as liquid crystal compositions and high-frequency components containing the same. Background Technology

[0002] Currently, optoelectronic display devices containing liquid crystal materials (LCDs) have achieved mass production and are widely used in various scenarios such as daily life, work, and production. Among them, LCD devices are most widely used in the consumer electronics field, mainly including: ① Televisions: LCD TVs are still the mainstream television type, offering a variety of options from small and medium sizes to giant screens; ② Computer monitors: They are widely used in everything from budget office screens to high-resolution screens for professional designers, and high refresh rate screens sought after by e-sports players; ③ Smartphones and tablets: They still hold an important share in the low-to-mid-range mobile phone market, and some tablets use LCD screens to balance performance and cost; ④ Digital cameras: Some viewfinders and rear displays still use LCD panels.

[0003] In recent years, with the continuous development of microwave and terahertz communication, optical communication, and laser phased array technologies, liquid crystal materials, as an important application direction of electromagnetic metamaterials, have received increasing attention. One of the most important applications is the liquid-crystal antenna, whose technical principle is based on the controllable dielectric anisotropy of liquid crystal materials. Liquid crystal materials exist in an intermediate state between liquid and solid, and their molecular arrangement has the characteristic of controllable order. When a voltage is applied, the liquid crystal molecules will reorient, causing a reversible change in the dielectric constant of the material. For example, at a frequency of 19 GHz, the Δε of some liquid crystal materials can be greater than 0.5. This characteristic allows for precise control of the propagation phase and direction of electromagnetic waves. Liquid crystal antennas control the phase and direction of electromagnetic waves through electrically controlled dielectric anisotropy. Their core advantage lies in integrating liquid crystal materials as millimeter-wave band phase shifters into microcircuits to achieve fast and stable beam control. This characteristic makes them irreplaceable in fields with high real-time requirements, such as military communications and satellite navigation. Current technology has broken through the bottlenecks of traditional antenna design, achieving lightweight and low-power phased array antennas by loading liquid crystal phase shifters.

[0004] However, the liquid crystal materials used as liquid crystal antennas still have the following problems:

[0005] Insufficiently high clearing point density poses a challenge for current liquid crystal monomers in meeting the requirements for high-temperature stability and a wide operating temperature range. Firstly, the core function of a liquid crystal antenna relies on the dielectric anisotropy modulation of liquid crystal molecules under external fields (such as electric or optical fields). Compounds with high clearing point density ensure that the liquid crystal material maintains stable dielectric properties in high-temperature environments (such as military equipment and satellite communications), preventing phase transitions (such as transformation into isotropic liquids) due to temperature increases, thus avoiding the loss of electrically tunable capabilities. Secondly, liquid crystal antennas need to adapt to extreme environments (such as deserts and space). Compounds with high clearing point density can extend the temperature range of the liquid crystal phase, for example, maintaining dielectric tunability from -20℃ to 150℃. If the clearing point density is too low, the disorder of liquid crystal molecules at high temperatures will lead to antenna performance failure.

[0006] In the microwave band, liquid crystals exhibit relatively high dielectric loss. Dielectric loss refers to the energy loss of insulating materials under alternating electric fields, resulting from mechanisms such as hysteresis in polarization, movement of conductive carriers, and space charge effects, in the conversion of electrical energy into heat. It is an important parameter for evaluating the insulation performance and energy conversion efficiency of dielectric materials, and is commonly characterized by the loss tangent (tanδ) or loss factor (DF). Under high-frequency microwave electric fields, the orientation polarization of liquid crystal molecules cannot be completely synchronized with changes in the electric field, easily leading to energy loss. Furthermore, high-frequency microwaves may induce chain vibrations in liquid crystal molecules, causing deformation or even local structural damage, increasing conductivity loss. Impurities or defects generated in liquid crystal molecules under high-frequency microwaves can exacerbate local electric field concentration, further increasing the dielectric loss (tanδ). High dielectric loss easily leads to problems such as increased device power consumption, decreased efficiency, and shortened lifespan. For liquid crystal molecules, the loss along the long axis and short axis is different; when calculating the loss of liquid crystal materials, the maximum loss value, max(tanδ), is generally used. ∥ ,tanδ ⊥ The dielectric loss of liquid crystal materials is a significant factor affecting the insertion loss of microwave devices. To obtain high-performance liquid crystal microwave devices, it is essential to reduce the dielectric loss of the liquid crystal material.

[0007] In the microwave band, liquid crystal materials currently exhibit low dielectric tuning efficiency (τ) and low quality factor (η). When microwave devices containing liquid crystal materials are used in liquid crystal antennas, the resonant frequency needs to be changed by an external electric field. The higher the dielectric tuning efficiency (τ) of the liquid crystal material, the higher its electric field modulation efficiency, enabling a wider tuning range and more sensitive frequency response. High dielectric tuning efficiency helps to quickly adjust the impedance matching between the device and the transmission line, reducing signal reflection loss and improving energy transmission efficiency. Specifically, the dielectric tuning efficiency (τ) is determined by the dielectric anisotropy (Δε) of the liquid crystal material at high frequencies and the dielectric constant (ε) in the direction parallel to the molecules. ∥ Determined by: τ=Δε / ε ∥To comprehensively evaluate the performance parameters of liquid crystal materials under microwave conditions, a quality factor parameter η is introduced: η = τ / max(tanδ) ∥ ,tanδ ⊥ A high quality factor η signifies a high dielectric tuning efficiency τ and a low dielectric loss tanδ. Liquid crystal materials with a high quality factor can reduce microwave energy dissipation within the material, thereby improving the frequency selectivity and signal transmission stability of the resonator. Currently, there is an urgent need for liquid crystal materials with large dielectric tuning efficiency τ and high quality factor η. Summary of the Invention

[0008] To address the aforementioned problems, this invention provides an isothiocyanate liquid crystal compound, a liquid crystal composition comprising the same, and a high-frequency component, thereby solving at least one of the aforementioned technical problems. The liquid crystal compound of this invention contains a benzofuran, benzothiophene, or benzoselenene structure in its main ring molecular structure. Liquid crystal compounds with this specific structure exhibit higher clearing point, lower dielectric loss, higher dielectric tuning efficiency τ, and higher quality factor η. Liquid crystal compositions containing this organic compound also exhibit higher clearing point, lower dielectric loss, higher dielectric tuning efficiency τ, and higher quality factor η. These compounds can be used to develop high-frequency components and devices for microwave applications, particularly microwave phase-shifting devices, tunable filters, tunable metamaterial structures, and electronically beam-controlled antennas (e.g., phase array antennas).

[0009] To solve the above-mentioned technical problems, the technical solution provided by the present invention is as follows:

[0010] In a first aspect, the present invention provides an isothiocyanate liquid crystal compound having the structure shown in formula (I):

[0011]

[0012] Formula I

[0013] in,

[0014] R1 and R2 are each independently selected from H, alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more unconnected -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0015] Q1 is selected from O, S, or Se;

[0016] Z1 and Z2 are each independently selected CH=CH , CF = CF , CH=CF , CF=CH , C≡C , C≡C C≡C Or a single key;

[0017] , Each represents independently or ;in, One or more unconnected -CH2- in a ring can be replaced by -O-, and a single bond in one or more rings can be replaced by a double bond; One or more H atoms may be replaced by F, Cl, alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms;

[0018] m1 represents 0, 1, or 2.

[0019] Compared to existing technologies, the isothiocyanate liquid crystal compound provided by this invention has a higher clearing point, lower dielectric loss, higher dielectric tuning efficiency τ, and higher quality factor η. The liquid crystal composition containing this organic compound also has a higher clearing point, lower dielectric loss, higher dielectric tuning efficiency τ, and higher quality factor η. It can be used to develop components and devices with high-frequency technology for microwave applications, especially microwave phase-shifting devices, tunable filters, tunable metamaterial structures, and electronic beam-controlled antennas (such as phase array antennas), with broad application prospects.

[0020] Furthermore, R1 and R2 are each independently selected from H, alkyl groups having 1-8 carbon atoms, alkoxy groups having 1-8 carbon atoms, alkenyl groups having 2-8 carbon atoms, or alkenoxy groups having 2-8 carbon atoms; wherein any one or more unconnected -CH2- groups in these groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0021] Q1 is selected from O or S;

[0022] Z1 and Z2 are each independently selected CH=CH , CF = CF , C≡C Or a single key;

[0023] , Each independently selected ;in, One or more H atoms can be replaced by F or CH3;

[0024] m1 represents 0 or 1.

[0025] Furthermore, R2 is H; R1 is selected from alkyl groups having 1-6 carbon atoms, alkoxy groups having 1-6 carbon atoms, or alkenyl groups having 2-6 carbon atoms; wherein any one or more unconnected -CH2- groups in these groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0026] Selected from , , , , , or ;

[0027] Selected from , , , or ;

[0028] The * end is connected to the NCS group.

[0029] In some examples, the compound represented by Formula I is selected from at least one of the following compounds:

[0030] Ⅰ-1-1、 Ⅰ-1-2、

[0031] Ⅰ-1-3、 Ⅰ-1-4、

[0032] Ⅰ-1-5、 Ⅰ-1-6、

[0033] Ⅰ-2-1、 Ⅰ-2-2、

[0034] Ⅰ-2-3、 Ⅰ-2-4、

[0035] Ⅰ-2-5、 Ⅰ-2-6、

[0036] Ⅰ-3-1、 Ⅰ-3-2、

[0037] Ⅰ-3-3、 Ⅰ-3-4、

[0038] Ⅰ-3-5、 Ⅰ-3-6、

[0039] Ⅰ-4-1、 Ⅰ-4-2、

[0040] Ⅰ-4-3、 Ⅰ-4-4、

[0041] Ⅰ-4-5、 Ⅰ-4-6、

[0042] Ⅰ-5-1、 Ⅰ-5-2、

[0043] Ⅰ-5-3、 Ⅰ-5-4、

[0044] Ⅰ-5-5、 Ⅰ-5-6

[0045] Among them, R 11 It is selected from alkyl, alkoxy, or alkenyl groups having 2-6 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl groups.

[0046] Q 11 Choose from O or S.

[0047] In some more specific examples, the compound represented by Formula I is selected from at least one of the following compounds:

[0048] Ⅰ-1-1-1、 Ⅰ-1-1-2、

[0049] Ⅰ-1-1-3、 Ⅰ-1-1-4、

[0050] Ⅰ-1-1-5、 Ⅰ-1-1-6、

[0051] Ⅰ-1-1-7、 Ⅰ-1-1-8、

[0052] Ⅰ-1-2-1、 Ⅰ-1-2-2、

[0053] Ⅰ-1-2-3、 Ⅰ-1-2-4、

[0054] Ⅰ-1-3-1、 Ⅰ-1-3-2、

[0055] Ⅰ-1-3-3、 Ⅰ-1-3-4、

[0056] Ⅰ-1-4-1、 Ⅰ-1-4-2、

[0057] Ⅰ-1-4-3、 Ⅰ-1-4-4、

[0058] Ⅰ-1-4-5、

[0059] Ⅰ-1-5-1、 Ⅰ-1-5-2、

[0060] Ⅰ-1-5-3、 Ⅰ-1-5-4、

[0061] Ⅰ-1-6-1、 Ⅰ-1-6-2、

[0062] Ⅰ-1-6-3、 Ⅰ-1-6-4、

[0063] Ⅰ-2-1-1、 Ⅰ-2-1-2、

[0064] Ⅰ-2-2-1、 Ⅰ-2-2-2、 Ⅰ-2-3-1、 Ⅰ-2-3-2、 Ⅰ-2-3-3、

[0065] Ⅰ-2-4-1、 Ⅰ-2-4-2、

[0066] Ⅰ-2-4-3、 Ⅰ-2-5-1、

[0067] Ⅰ-2-5-2、 Ⅰ-2-5-3、

[0068] Ⅰ-2-6-1、 Ⅰ-2-6-2、

[0069] Ⅰ-2-6-3、

[0070] Ⅰ-3-1-1、 Ⅰ-3-1-2、

[0071] Ⅰ-3-1-3、

[0072] Ⅰ-3-2-1、 Ⅰ-3-2-2、

[0073] Ⅰ-3-2-3、 Ⅰ-3-2-4、

[0074] Ⅰ-3-3-1、 Ⅰ-3-3-2、

[0075] Ⅰ-3-3-3、

[0076] Ⅰ-3-4-1、 Ⅰ-3-4-2、

[0077] Ⅰ-3-5-1、 Ⅰ-3-5-2、

[0078] Ⅰ-3-5-3、 Ⅰ-3-6-1、

[0079] Ⅰ-3-6-2、 Ⅰ-3-6-3、

[0080] Ⅰ-4-1-1、 Ⅰ-4-1-2、

[0081] Ⅰ-4-1-3、

[0082] Ⅰ-4-2-1、 Ⅰ-4-2-2、

[0083] Ⅰ-4-3-1、 Ⅰ-4-3-2、

[0084] Ⅰ-4-3-3、 Ⅰ-4-4-1、

[0085] Ⅰ-4-4-2、 Ⅰ-4-5-1、

[0086] Ⅰ-4-5-2、 Ⅰ-4-5-3、

[0087] Ⅰ-4-6-1、 Ⅰ-4-6-2、

[0088] Ⅰ-4-6-3、

[0089] Ⅰ-5-1-1、 Ⅰ-5-1-2、

[0090] Ⅰ-5-1-3、

[0091] Ⅰ-5-2-1、 Ⅰ-5-2-2、

[0092] Ⅰ-5-2-3、 Ⅰ-5-2-4、

[0093] Ⅰ-5-3-1、 Ⅰ-5-3-2、

[0094] Ⅰ-5-3-3、 Ⅰ-5-4-1、

[0095] Ⅰ-5-4-2、 Ⅰ-5-5-1、

[0096] Ⅰ-5-5-2、 Ⅰ-5-6-1、

[0097] Ⅰ-5-6-2.

[0098] In a second aspect, the present invention provides a liquid crystal composition comprising one or more isothiocyanate liquid crystal compounds of formula (I).

[0099] Furthermore, the content of the isothiocyanate liquid crystal compound represented by formula (Ⅰ) in the liquid crystal composition is 0.1%-60% by mass percentage.

[0100] Regarding the preferred mass percentage of the compound represented by Formula I in the liquid crystal composition of the present invention: the preferred lower limit value of the mass percentage of the liquid crystal compound of Formula I relative to the total mass of the liquid crystal composition of the present invention is 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 10%, 15%, 20%, 25% or 30%; the preferred upper limit value of the mass percentage of the liquid crystal compound of Formula I relative to the total mass of the liquid crystal composition of the present invention is 60%, 50%, 40%, 30%, 25% or 10%.

[0101] 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, 0.1%-60%, 1%-50%, 1%-30%, 3%-25%, 3%-20%, 3%-15%, 3%-10%, 10%-15%, etc.

[0102] In the liquid crystal composition, the compound represented by Formula I is used as a liquid crystal antenna element. Preferably, by controlling the content of the compound represented by Formula (I) in the liquid crystal composition, the liquid crystal composition can have a higher clearing point, lower dielectric loss, higher dielectric tuning rate τ, and higher quality factor η.

[0103] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula (II):

[0104]

[0105] Formula (II)

[0106] in,

[0107] R3 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0108] , Each independently selected , , or ;

[0109] Z3 and Z4 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or CH2CH2- ;

[0110] m2 represents 0, 1, or 2.

[0111] In some examples, the compound represented by formula (II) is selected from formula II. Formulas 1 to 2 Group consisting of compounds shown in Figure 8:

[0112] II-1 II-2

[0113] II-3 II-4

[0114] II-5 II-6

[0115] II-7 II-8.

[0116] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula (Ⅲ):

[0117]

[0118] Formula (III)

[0119] in,

[0120] R4 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more of these groups may have one or more non-attached -CH2- groups replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0121] , Each independently selected , , or ;

[0122] Z5 and Z6 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or CH2CH2- ;

[0123] m3 represents 0, 1, or 2.

[0124] In some examples, the compound represented by formula (Ⅲ) is selected from formula III. Formulas 1 to 3 Group consisting of compounds shown in Figure 8:

[0125] Ⅲ-1、 Ⅲ-2、

[0126] Ⅲ-3、 Ⅲ-4、

[0127] Ⅲ-5、 Ⅲ-6、

[0128] Ⅲ-7、 Ⅲ-8.

[0129] More preferably, the compound represented by formula (Ⅲ) is selected from formula III. 5. Formula III 6. Formula III Type 7 III Group consisting of compounds shown in Figure 8:

[0130] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula (Ⅳ):

[0131]

[0132] Equation (Ⅳ)

[0133] in,

[0134] R5 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more of these groups may have one or more non-connected -CH2- replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0135] , Each independently selected , , or ;

[0136] Z7 and Z8 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or CH2CH2- ;

[0137] m4 represents 0, 1, or 2.

[0138] In some examples, the compound represented by formula (Ⅳ) is selected from formula IV. Formulas 1 to IV Group consisting of compounds shown in Figure 8:

[0139] IV-1 IV-2

[0140] IV-3 IV-4

[0141] IV-5 IV-6

[0142] IV-7 IV-8.

[0143] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula (V):

[0144]

[0145] Formula (V)

[0146] in,

[0147] R6 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0148] , Each independently selected , , or ;

[0149] Z a Z b Each is independently selected from a single bond, -C≡C-, -CH=CH-, -CF=CF-, or CH2CH2- ;

[0150] m5 represents 0, 1, or 2.

[0151] In some examples, the compound represented by formula (V) is selected from formula V. 1 to Formula V Group consisting of compounds shown in Figure 8:

[0152] V-1 V-2,

[0153] V-3 V-4

[0154] V-5 V-6

[0155] V-7 V-8.

[0156] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula (VI):

[0157]

[0158] Formula (VI)

[0159] in,

[0160] and Each independently selected , or ;in One or more unconnected -CH2- can be replaced by -O-. The H atom in the middle can be replaced by F;

[0161] R7 and R8 are each independently selected from alkyl groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkynyl groups having 2-10 carbon atoms;

[0162] Z c Selected from -CO-O-, -O-CO-, -CH=CH-, -C≡C- or single bonds;

[0163] m6 represents 2, 3, or 4;

[0164] When m6 represents 2, 3 or 4 Same or different, Z c Same or different.

[0165] In some examples, the compound represented by formula (VI) is selected from formula VI. Formula 1 to Formula VI The group consisting of the compounds shown in Figure 6:

[0166] VI-1 VI-2

[0167] VI-3 VI-4

[0168] VI-5 VI-6.

[0169] It should be noted that the present invention does not impose any particular limitation on the synthesis method of the compounds shown in formulas (I)-(VI), which can be prepared by known methods. The liquid crystal composition is prepared by conventional methods. Typically, the components are mixed and heated to dissolve each other until the dissolution process is observed to be complete. Alternatively, all components can be dissolved in a suitable organic solvent, and the solvent removed after thorough mixing to finally obtain a homogeneous liquid crystal composition.

[0170] As a specific embodiment of the present invention, the preparation method of the liquid crystal composition is as follows: each liquid crystal monomer (i.e. each compound) is weighed according to a certain ratio and placed into a stainless steel beaker. The stainless steel beaker containing each liquid crystal monomer is placed on a magnetic stirrer and heated to melt. After most of the liquid crystal monomers in the stainless steel beaker have melted, a magnetic rotor is added to the stainless steel beaker to stir the mixture evenly. The mixture is then cooled to room temperature to obtain the liquid crystal composition.

[0171] In this embodiment, various functional additives can be added to the liquid crystal compound. The mass percentage of each additive is relative to the total mass of all liquid crystal compounds excluding the additives. For example, the mass percentage of the additives is preferably between 0.01% and 2%. These additives are mainly chiral agents, antioxidants, light stabilizers, ultraviolet absorbers, polymerizable monomers, self-aligning agents, etc.

[0172] For example, antioxidant and light stabilizer additives are selected from the following compounds:

[0173]

[0174]

[0175] For example, the ultraviolet absorber additive is selected from the following compounds:

[0176]

[0177] For example, polymerizable monomer additives are selected from the following compounds:

[0178]

[0179]

[0180] .

[0181] It should be noted that the specific content of the liquid crystal compounds of formulas II, III, IV, V and VI in the liquid crystal composition can be obtained by those skilled in the art through conventional adjustments, and the present invention does not impose any special limitations.

[0182] Specifically, relative to the total mass of the liquid crystal composition of the present invention, the content of the compound represented by Formula II in the liquid crystal composition is 1%-30%. 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, 2%-20%, 4%-19%, 4%-15%, 12%-15%, etc.

[0183] Specifically, relative to the total mass of the liquid crystal composition of the present invention, the content of the compound represented by Formula III in the liquid crystal composition is 1%-90%. In some specific examples, the content of the compound represented by Formula III in the liquid crystal composition, by mass percentage, includes, but is not limited to, 1%-80%, 8%-70%, 35%-70%, 9%-35%, 9%-28%, 28%-35%, etc.

[0184] Specifically, relative to the total mass of the liquid crystal composition of the present invention, the content of the compound represented by Formula IV in the liquid crystal composition is 1%-40%. In some specific examples, the content of the compound represented by Formula IV in the liquid crystal composition, by mass percentage, includes, but is not limited to, 1%-30%, 3%-25%, 6%-25%, 6%-15%, 3%-6%, 15%-25%, etc.

[0185] Specifically, relative to the total mass of the liquid crystal composition of the present invention, the content of the compound represented by formula V in the liquid crystal composition is 1%-60%. 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, 6%-60%, 36%-60%, 6%-18%, 18%-36%, 10%-18%, 6%-10%, etc.

[0186] Specifically, relative to the total mass of the liquid crystal composition of the present invention, the content of the compound represented by formula VI in the liquid crystal composition is 1%-60%. In some specific examples, the content of the compound represented by formula VI in the liquid crystal composition, by mass percentage, includes, but is not limited to, 1%-55%, 2%-50%, 3%-40%, etc.

[0187] It should be noted that, in this invention, the elements contained in the compounds include all their corresponding isotopes, such as compounds in which H, C, N, O, Cl, F, S, Se, etc. have been replaced by their corresponding isotopes, and this is particularly preferred in some embodiments.

[0188] Thirdly, the present invention provides a high-frequency component comprising one or more liquid crystal compositions as described above.

[0189] Specifically, the high-frequency components are liquid crystal-based antenna elements, phase shifters, tunable filters, tunable metamaterial structures, matching networks, or varactor diodes.

[0190] Fourthly, the present invention provides a microwave antenna array comprising the high-frequency components described above.

[0191] The liquid crystal compositions of the present invention are suitable for fabricating high-frequency components, such as microwave components, and more specifically, phase shifters that can be tuned by an applied magnetic or electric field. These phase shifters can operate in UHF... Frequency band (0.3-1GHz), L Frequency band (1-2GHz), S Frequency band (2-4GHz), C Frequency band (4-8GHz), X Frequency band (8-12GHz), Ku Frequency band (12-18GHz), K Frequency band (18-27GHz), Ka Frequency band (27-40GHz), V Frequency band (50-75GHz), W Operating frequency band (75-110 GHz) and up to 1 THz. The construction of the phase shifter according to the invention is known to those skilled in the art. Typically, loaded line phase shifters, inverted microstrip line phase shifters, finline phase shifters, preferably antipodal finline phase shifters, slotted phase shifters, microstrip line phase shifters, or coplanar waveguide (CPW) phase shifters are used. These components enable reconfigurable antenna arrays. Attached Figure Description

[0192] Figure 1 The mass spectrum of the compound represented by formula I-3-1-1 obtained in synthesis example 4;

[0193] Figure 2 The mass spectrum is shown for the compound represented by formula I-5-1-1 obtained in synthesis example 5. Detailed Implementation

[0194] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0195] Unless otherwise specified in the specific embodiments of this invention, percentages refer to mass percentages, temperatures are in degrees Celsius (°C), and the specific meanings and test conditions of other symbols are as follows:

[0196] Cp represents the liquid crystal clearing point (°C), measured by DSC quantitative method;

[0197] 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 were 25±0.5℃, 20μm vertical cell, and INSTEC:ALCT-IR1 test.

[0198] K 11 K is the elastic constant of the development. 33 The bending elastic constant was determined under the following test conditions: 25℃, INSTEC:ALCT-IR1, and a 20μm VA vertical box.

[0199] γ1 represents rotational viscosity (mPa·s), and the test conditions are 25±0.5℃, 20μm vertical box, INSTEC: ALCT-IR1 test;

[0200] The performance (dielectric constant, dielectric loss) of the liquid crystal composition at high frequencies (19 GHz) in this paper was tested using the method reported in the literature (Penirschke, A. (2004). Cavity perturbation method for characterization of liquid crystals up to 35 GHz. Microwave Conference, 2004. 34th European). The specific steps are as follows: First, the dissolved liquid crystal composition was introduced into a capillary made of polytetrafluoroethylene (PTFE). The capillary filled with the liquid crystal composition was then placed at the center of a cavity resonator with a resonant frequency of 19 GHz. Next, an input signal source was applied, and the output signal was recorded using a network analyzer. The changes in the resonant frequency and Q factor between the liquid crystal-filled capillary and the blank capillary were measured, and the dielectric constant and loss tangent were calculated. The dielectric constant components perpendicular to and parallel to the liquid crystal director were obtained by aligning the liquid crystal in a magnetic field. The direction of the magnetic field was set accordingly, and then rotated by 90° accordingly.

[0201] Dielectric anisotropy in the microwave range is defined as Δε≡ε ∥ -ε ⊥ (19GHz, 25℃);

[0202] Tunerness (τ) is defined as τ ≡ Δε / ε ∥ (19GHz, 25℃), the higher the value, the better the performance;

[0203] The material quality factor (η) is defined as η≡τ / (tanδε,max) (19GHz, 25℃), and a larger value indicates better performance; among which, the maximum dielectric loss (tanδε,max) is defined as (tanδε,max)=max(tanδε,max) ∥ ,tanδ ⊥ The smaller the value, the better the performance.

[0204] The following is a method for preparing the isothiocyanate compound shown in formula (Ⅰ) used in the examples. The following synthetic route is preferred, and other similar structures can also be prepared using this method.

[0205]

[0206] R1 represents H, an alkyl group having 1-8 carbon atoms, an alkoxy group having 1-8 carbon atoms, an alkenyl group having 2-8 carbon atoms, or an alkenoxy group having 2-8 carbon atoms, wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0207] Q1 represents O or S;

[0208] n represents 0 or 1;

[0209] The same or different meanings each time it appears , , or .

[0210]

[0211] R1 represents H, an alkyl group having 1-8 carbon atoms, an alkoxy group having 1-8 carbon atoms, an alkenyl group having 2-8 carbon atoms, or an alkenoxy group having 2-8 carbon atoms, wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene.

[0212] Q1 represents O or S;

[0213] n represents 0 or 1;

[0214] The same or different meanings each time it appears , , or .

[0215] To better illustrate the present invention, further examples are provided below.

[0216] Synthesis Example 1

[0217] Preparation of liquid crystal compound I-1-4-1:

[0218] The preparation route is as follows:

[0219]

[0220] Specific preparation procedure:

[0221] 25.5 g of compound 1 and 31.8 g of compound 2 were dissolved in a mixed solution of 300 ml toluene and 60 ml water. 16.6 g of potassium carbonate and Pd-132 were added, nitrogen gas was purged, and the mixture was refluxed for 2 hours. The mixture was cooled to room temperature, 200 ml of water and 300 ml of toluene were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 ml of toluene. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and recrystallized with 200 ml of anhydrous ethanol at room temperature. The mixture was filtered to obtain 36.0 g of white solid compound 3.

[0222] 36.0 g of compound 3 and 11.7 g of p-aminophenylacetylene were dissolved in a mixed solution of 400 ml toluene and 100 ml triethylamine. 0.38 g of cuprous iodide and 2.3 g of tetrakis(triphenylphosphine)palladium were added, nitrogen was purged, and the mixture was refluxed for 8 hours. The mixture was then cooled to room temperature, filtered, and the filtrate was concentrated and purified by column chromatography to obtain 32.3 g of yellow solid compound 4.

[0223] 32.3 g of compound 4 and 21.7 g of 1,1'-thiocarbonylbis-2(1H)-pyridone were dissolved in 400 ml of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. 400 ml of water and 200 ml of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 200 ml of dichloromethane. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and purified by column chromatography to obtain 24.9 g of a white solid, the compound shown in formula I-1-4-1.

[0224] Following the above method, in step 1 of the synthesis example, 5-pentylbenzo[b]furan-2-boric acid was replaced with other substituted benzo[b]furan-2-boric acid in step 1, coupled with compound 2, then coupled with p-aminophenylacetylene, and finally rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-1-4-2, I-1-4-3, and I-1-4-4.

[0225] Following the above method, in the synthesis example 1, 5-pentylbenzo[b]furan-2-boric acid was replaced with other substituted benzo[b]furan-2-boric acid in step 1. After coupling with compound 2, the substrate was deprotonated / lithiated with n-butyllithium under low temperature conditions, followed by nucleophilic borylation reaction with trimethyl borate, acid hydrolysis to obtain the corresponding boric acid, which was then coupled with each corresponding substituted p-aminobromobenzene. Finally, a rearrangement reaction was carried out with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-1-3-1, I-1-3-2, I-1-3-3, I-3-3-1, I-3-3-2, I-4-1-1, I-4-1-2, I-5-3-1, I-5-3-2, etc.

[0226] Benzo[b]furan-2-boronic acid substituted with linear alkyl, alkoxy, alkenyl, or cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl chains is commercially available. The principles, procedures, routine post-treatments, silica gel column chromatography, recrystallization purification, and other techniques of this method are well known to those skilled in the art, and the synthesis process can be fully realized to obtain the target product.

[0227] Synthesis Example 2

[0228] Preparation of liquid crystal compound I-1-4-5:

[0229] The preparation route is as follows:

[0230]

[0231] Specific preparation procedure:

[0232] 27.2 g of compound 5 and 31.8 g of compound 2 were dissolved in a mixed solution of 300 ml toluene and 60 ml water. 16.6 g of potassium carbonate and Pd-132 were added, nitrogen gas was purged, and the mixture was refluxed for 2 hours. After cooling to room temperature, 200 ml of water and 300 ml of toluene were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 ml of toluene. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and recrystallized with 200 ml of anhydrous ethanol at room temperature. The mixture was filtered to obtain 37.5 g of white solid compound 6.

[0233] 37.5 g of compound 6 and 11.7 g of p-aminophenylacetylene compound were dissolved in a mixed solution of 400 ml toluene and 100 ml triethylamine. 0.38 g of cuprous iodide and 2.3 g of tetrakis(triphenylphosphine)palladium were added, nitrogen was purged, and the mixture was refluxed for 8 hours. The mixture was then cooled to room temperature, filtered, and the filtrate was concentrated and purified by column chromatography to obtain 32.8 g of yellow solid compound 7.

[0234] 32.8 g of compound 7 and 21.2 g of 1,1'-thiocarbonyldi-2(1H)-pyridone were dissolved in 400 ml of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. 400 ml of water and 200 ml of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 200 ml of dichloromethane. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and purified by column chromatography to obtain 23.4 g of white solid compound of formula I-1-4-5.

[0235] Following the above method, in the synthesis example 2, 5-pentylbenzo[b]thiophene-2-boric acid was replaced with other substituted benzo[b]thiophene-2-boric acid in step 1, coupled with p-bromoiodobenzene, then coupled with p-aminophenylacetylene with different fluorine substitution positions, and finally rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-2-4-3, I-4-4-2, I-5-4-2.

[0236] Following the above method, in the synthesis example 2, in step 1, 5-pentylbenzo[b]thiophene-2-boric acid was replaced with other substituted benzo[b]thiophene-2-boric acid. After coupling with compound 2, the substrate was deprotonated / lithiated with n-butyllithium under low temperature conditions, followed by nucleophilic borylation reaction with trimethyl borate, acid hydrolysis to obtain the corresponding boric acid, then coupled with various substituted p-aminobromobenzene, and finally rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-1-3-4, I-3-3-3, I-4-1-3, I-5-3-3, etc.

[0237] Synthesis Example 3

[0238] Preparation of liquid crystal compound I-3-4-1:

[0239] The preparation route is as follows:

[0240]

[0241] Specific preparation procedure:

[0242] 25.5 g of compound 1 and 13.6 g of compound 8 were dissolved in a mixed solution of 300 ml toluene and 60 ml water. 16.6 g of potassium carbonate and Pd-132 were added, nitrogen was purged, and the mixture was refluxed for 2 hours. The mixture was cooled to room temperature, and 200 ml of water and 300 ml of toluene were added. The mixture was extracted and the phases were separated. The aqueous phase was extracted with 2 × 100 ml of toluene. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and recrystallized at room temperature with 100 ml of anhydrous ethanol and 50 ml of petroleum ether. The mixture was filtered to obtain 24.8 g of yellow solid compound 9.

[0243] 24.8 g of compound 9 and 23.02 g of compound 2 were dissolved in a mixed solution of 300 ml toluene and 75 ml triethylamine. 0.38 g of cuprous iodide and 2.3 g of tetrakis(triphenylphosphine)palladium were added, nitrogen was purged, and the mixture was refluxed for 8 hours. The mixture was then cooled to room temperature, filtered, and the filtrate was concentrated and purified by column chromatography to obtain 30.37 g of yellow solid compound 10.

[0244] 30.37 g of compound 10 and 20.4 g of 1,1'-thiocarbonylbis-2(1H)-pyridone were dissolved in 300 ml of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. 400 ml of water and 200 ml of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 200 ml of dichloromethane. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and purified by column chromatography to obtain 25.3 g of a white solid, the compound shown in formula I-3-4-1.

[0245] Following the above method, in step 1 of synthesis Example 3, 5-butylbenzo[b]furan-2-boric acid was used to replace 5-pentylbenzo[b]furan-2-boric acid. After coupling with substituted p-chlorophenylacetylene, it was coupled with substituted p-iodoaniline, and finally rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-2-4-1, I-2-4-2, I-3-4-2, I-4-4-1, I-5-4-1, etc.

[0246] Benzo[b]furan-2-boronic acid substituted with linear alkyl, alkoxy, alkenyl, or cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl chains is commercially available. The principles, procedures, routine post-treatments, silica gel column chromatography, recrystallization purification, and other techniques of this method are well known to those skilled in the art, and the synthesis process can be fully realized to obtain the target product.

[0247] Synthesis Example 4

[0248] Preparation of liquid crystal compound I-3-1-1:

[0249] The preparation route is as follows:

[0250]

[0251] Specific preparation procedure:

[0252] 25.5 g of compound 1 and 20.8 g of compound 2 were dissolved in a mixed solution of 300 ml toluene and 60 ml water. 16.6 g of potassium carbonate and Pd-132 were added, and the mixture was refluxed under nitrogen for 2 hours. The mixture was then cooled to room temperature, and 200 ml of water and 300 ml of toluene were added. The mixture was extracted and the phases separated. The aqueous phase was extracted with 2 × 100 ml of toluene. The organic phases were combined, washed with 300 ml of saturated brine, dried, and concentrated. The mixture was recrystallized from 200 ml of anhydrous ethanol at room temperature and filtered to give 29.9 g of white solid compound 12.

[0253] 29.9 g of compound 12 and 26.4 g of 1,1'-thiocarbonyldi-2(1H)-pyridone were dissolved in 300 mL of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. 300 mL of water and 100 mL of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 mL of dichloromethane. The organic phases were combined, washed with 300 mL of saturated brine, dried, concentrated, and purified by column chromatography to give 28.8 g of a white solid, the compound shown in formula I-3-1-1.

[0254] The mass spectrum of the compound represented by formula I-3-1-1 is as follows: Figure 1 As shown.

[0255] Following the above method, in step 1 of synthesis example 4, 5-pentylbenzo[b]thiophene-2-boric acid was replaced with other substituted benzo[b]furan-2-boric acid, coupled with substituted p-bromoaniline, and then rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compounds: I-1-1-1, I-1-1-2, I-1-1-3, I-1-1-4, I-2-1-1, I-2-1-2, I-3-1-2, I-3-1-3, etc.

[0256] Benzo[b]furan-2-boronic acid substituted with linear alkyl, alkoxy, alkenyl, or cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl chains is commercially available. The principles, procedures, routine post-treatments, silica gel column chromatography, recrystallization purification, and other techniques of this method are well known to those skilled in the art, and the synthesis process can be fully realized to obtain the target product.

[0257] Synthesis Example 5

[0258] Preparation of liquid crystal compound I-5-1-1:

[0259] The preparation route is as follows:

[0260]

[0261] Specific preparation procedure:

[0262] 25.5 g of compound 1 and 24.3 g of compound 13 were dissolved in a mixed solution of 300 ml toluene and 60 ml water. 16.6 g of potassium carbonate and Pd-132 were added, nitrogen gas was purged, and the mixture was refluxed for 2 hours. The mixture was cooled to room temperature, 200 ml of water and 300 ml of toluene were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 ml of toluene. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and recrystallized with 200 ml of anhydrous ethanol at room temperature. The mixture was filtered to obtain 31.6 g of white solid 14.

[0263] 31.6 g of compound 14 and 25 g of 1,1'-thiocarbonyldi-2(1H)-pyridone were dissolved in 300 mL of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. Then, 300 mL of water and 100 mL of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted again with 2 × 100 mL of dichloromethane. The organic phases were combined, washed with 300 mL of saturated brine, dried, and concentrated. The mixture was purified by column chromatography to give 28.3 g of the white solid shown in I-5-1-1.

[0264] The mass spectrum of the compound represented by formula I-5-1-1 is as follows: Figure 2 As shown.

[0265] Following the above method, in step 1 of synthesis example 5, 5-pentylbenzo[b]thiophene-2-boric acid was replaced with other substituted benzo[b]furan-2-boric acid, coupled with compound 13, and then rearranged with 1,1'-thiocarbonylbis-2(1H)-pyridone to obtain the following liquid crystal compound: I-5-1-2.

[0266] Straight-chain alkyl and alkoxy-substituted benzo[b]furan-2-boronic acid can be obtained commercially. The principles, operation procedures, routine post-treatment, silica gel column chromatography, recrystallization purification, and other methods of such synthesis are well known to those skilled in the art, and the synthesis process can be fully realized to obtain the target product.

[0267] Synthesis Example 6

[0268] Preparation of liquid crystal compound I-4-2-1:

[0269] The preparation route is as follows:

[0270]

[0271] Specific preparation procedure:

[0272] 26.7 g of compound 15 and 11.76 g of trimethylsilylacetylene were dissolved in 300 ml of triethylamine. 0.38 g of cuprous iodide and 2.3 g of tetrakis(triphenylphosphine)palladium were added, nitrogen was purged, and the mixture was refluxed for 4 hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated. Column chromatography was performed using petroleum ether as eluent. The solution was concentrated to give a yellow oily liquid. One part anhydrous ethanol was added, and the mixture was recrystallized at -20 °C. The solution was filtered to give 22.75 g of white solid 16.

[0273] 22.75 g of compound 16 was dissolved in 300 ml of tetrahydrofuran, cooled to 0 °C, and 30.28 g of tetrabutylammonium fluoride was added in portions. After the addition was complete, the mixture was left at room temperature overnight. 300 ml of water and 200 ml of ethyl acetate were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 ml of ethyl acetate. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and subjected to column chromatography with petroleum ether as the eluent. The solution was concentrated to give a yellow oily liquid. One part anhydrous ethanol was added, and the mixture was recrystallized at -20 °C. The solution was filtered to give 15.28 g of white solid 17.

[0274] 15.28 g of compound 17 and 15.72 g of compound 18 were dissolved in a mixed solution of 200 ml toluene and 50 ml triethylamine. 0.19 g of cuprous iodide and 1.15 g of tetra(triphenylphosphine)palladium were added, nitrogen was purged, and the mixture was refluxed for 8 hours. The mixture was then cooled to room temperature, filtered, and the filtrate was concentrated and purified by column chromatography to obtain 20.03 g of yellow solid 19.

[0275] 20.03 g of compound 19 and 16.4 g of 1,1'-thiocarbonylbis-2(1H)-pyridone were dissolved in 200 ml of dichloromethane solution, purged with nitrogen, and reacted at room temperature for 8 hours. 200 ml of water and 200 ml of dichloromethane were added, and the mixture was extracted and separated. The aqueous phase was extracted with 2 × 100 ml of dichloromethane. The organic phases were combined, washed with 300 ml of saturated brine, dried, concentrated, and purified by column chromatography to obtain 12.3 g of a white solid, the compound shown in formula I-4-2-1.

[0276] Following the above method, in the synthesis example 6, in step 1, 5-pentylbenzo[b]thiophene-2-bromo was replaced with other substituted benzo[b]furan-2-bromo, coupled with trimethylsilylacetylene, desilication by tetrabutylammonium fluoride, coupled with substituted p-bromoaniline, and then rearranged with 1,1'-thiocarbonyldi-2(1H)-pyridone to obtain the following liquid crystal compounds: I-1-2-1, I-1-2-2, I-1-2-3, I-2-2-1, I-3-2-1, I-3-2-2, I-4-2-2, I-5-2-1, I-5-2-2, etc.

[0277] Benzo[b]furan-2-bromo substituted with straight-chain alkyl, alkoxy, alkenyl, or cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl compounds is commercially available. The principles, procedures, routine post-treatments, silica gel column chromatography, recrystallization purification, and other techniques of such methods are well known to those skilled in the art, and the synthesis process can be fully realized to obtain the target product.

[0278] Application Examples

[0279] The liquid crystal monomer structure in the application embodiments of the present invention is represented by code. The code representation methods of liquid crystal ring structure, end group and linking group are shown in Table 1 and Table 2 below.

[0280] Table 1. Corresponding codes for ring structures

[0281]

[0282] Table 2. Correspondence codes between end groups and linking groups

[0283]

[0284] For example:

[0285] Its code is CC-Cp-V1;

[0286] Its code is PGP-Cpr1-2;

[0287] Its code is CPY-2-O2;

[0288] Its code is CCY-3-O2;

[0289] Its code is COY-3-O2;

[0290] Its code is CCOY-3-O2;

[0291] Its code is Sb-CpO-O4;

[0292] Its code is Sc-CpO-O4;

[0293] Its code is CCU-3-F;

[0294] Its code is PGU-3-F;

[0295] Its code is CCPU-3-F;

[0296] Its code is CPGU-3-OT;

[0297] Its code is DGUQU-4-F;

[0298] Its code is PGUQU-3-F;

[0299] Its code is PPGU-Cp-F.

[0300] The liquid crystal compounds represented by Formula I involved in the various application examples and comparative examples are shown in Table 3 below.

[0301] Table 3. Liquid crystal compounds involved in the application examples and comparative examples.

[0302]

[0303] The following application examples and comparative examples show the preparation methods of the liquid crystal compositions:

[0304] Each liquid crystal monomer (i.e. each compound) is weighed according to a certain ratio and placed into a stainless steel beaker. The stainless steel beaker containing each liquid crystal monomer is placed on a magnetic stirrer and heated to melt. After most of the liquid crystal monomers in the stainless steel beaker have melted, a magnetic rotor is added to the stainless steel beaker to stir the mixture evenly. After cooling to room temperature, the liquid crystal composition is obtained.

[0305] Application Examples 1-2 and Comparative Examples 1-2

[0306] Liquid crystal compositions for Application Comparative Example 1, Application Example 1, Application Comparative Example 2, and Application Example 2 were prepared according to the compounds listed in Table 4 and their corresponding mass percentages, and were introduced into capillaries made of polytetrafluoroethylene (PTFE) for performance testing. The test results are shown in Table 5 below.

[0307] Table 4. Formulation composition of the liquid crystal compositions in Application Examples 1-2 and Comparative Examples 1-2

[0308]

[0309] The prepared liquid crystal composition was introduced into a capillary made of polytetrafluoroethylene (PTFE) for performance testing, and the results are shown in Table 5.

[0310] Table 5. Test results of performance parameters of the liquid crystal compositions in Application Examples 1-2 and Comparative Examples 1-2

[0311]

[0312] Comparing the performance of the liquid crystal compositions in Application Examples 1-1 and 1-2 with those in Application Comparative Examples 1-1 and 1-2, it can be seen that: compared with Application Comparative Examples 1-1 and 1-2, I-1-4-1 and I-1-4-2 in Application Examples 1-1 and 1-2 of the present invention replaced the comparative compounds D1-1 and D1-2, respectively. The performance results show that the formulation has a higher clearing point, lower dielectric loss, higher dielectric tuning rate, and higher quality factor η. Therefore, it can be inferred that the monomers in Application Examples 1-1 and 1-2 have significantly improved performance compared with the monomers in Application Comparative Example 1.

[0313] Similarly, it can be seen that the monomers in Application Examples 2-1 and 2-2 have significantly improved performance compared to those in Comparative Examples 2-1 and 2-2.

[0314] Application Examples 3 and 4 and Comparative Examples 3 and 4

[0315] Liquid crystal compositions for Application Comparative Example 3, Application Example 3, Application Comparative Example 4, and Application Example 4 were prepared according to the compounds listed in Table 6 and their corresponding mass percentages. The prepared liquid crystal compositions were then introduced into capillaries made of polytetrafluoroethylene (PTFE) for performance testing. The test results are shown in Table 7 below.

[0316] Table 6. Formulation composition of the liquid crystal compositions in Application Examples 3 and 4 and Comparative Examples 3 and 4

[0317]

[0318] Table 7. Test results of performance parameters of the liquid crystal compositions in Application Examples 3 and 4 and Comparative Examples 3 and 4

[0319]

[0320] Comparing the performance of the liquid crystal compositions in Application Examples 3-1 and 3-2 with those in Application Comparative Example 3, it can be seen that: compared with Application Comparative Example 3, I-3-4-1 and I-3-4-2 in Application Examples 3-1 and 3-2 of the present invention replaced the comparative compound D3, respectively. The performance results show that the formulation has a higher clearing point, lower dielectric loss, higher dielectric tuning rate, and higher quality factor η. Therefore, it can be inferred that the monomers in Application Examples 3-1 and 3-2 have significantly improved performance compared with the monomers in Application Comparative Example 3.

[0321] Similarly, it can be seen that the monomers in Application Examples 4-1 and 4-2 show significantly improved performance compared to the monomers in Comparative Example 4.

[0322] Application Example 5 and Application Comparative Example 5

[0323] Liquid crystal compositions for Application Comparative Example 5 and Application Example 5 were prepared according to the compounds listed in Table 8 and their corresponding mass percentages, respectively. The prepared liquid crystal compositions were then introduced into capillaries made of polytetrafluoroethylene (PTFE) for performance testing. The test results are shown in Table 9 below.

[0324] Table 8. Formulation composition of the liquid crystal compositions in Application Example 5 and Comparative Example 5

[0325]

[0326] Table 9. Test results of performance parameters of the liquid crystal compositions in Application Example 5 and Comparative Example 5

[0327]

[0328] Comparing the performance of the liquid crystal compositions in Application Examples 5-1 and 5-2 with those in Application Comparative Example 5, it can be seen that: compared with Application Comparative Example 5, I-5-1-1 and I-5-1-2 in Application Examples 5-1 and 5-2 of the present invention respectively replaced the comparative compound D5. From the performance results, it can be found that the formulation has a higher clearing point, lower dielectric loss, higher dielectric tuning rate, and higher quality factor η. Therefore, it can be inferred that the monomers in Application Examples 5-1 and 5-2 have significantly improved performance compared with the monomers in Application Comparative Example 5.

[0329] Application Examples 6, 7 and 8

[0330] Liquid crystal compositions for Application Examples 6, 7, and 8 were formulated according to the compounds listed in Tables 10, 11, and 12 and their corresponding mass percentages, and were introduced into capillaries made of polytetrafluoroethylene (PTFE) for performance testing. The test results are shown in Table 13 below.

[0331] In Table 10, the mass percentage of each compound described in numbers 1-17 is relative to the total mass of the compounds described in numbers 1-17; the mass percentage of the compound described in number 18 is also relative to the total mass of the compounds described in numbers 1-17.

[0332] In Table 11, the mass percentage of each of the compounds listed in numbers 1-16 is relative to the total mass of the compounds listed in numbers 1-16.

[0333] In Table 12, the mass percentage of each compound described in numbers 1-19 is relative to the total mass of the compounds described in numbers 1-19; the mass percentage of the compound described in number 20 is also relative to the total mass of the compounds described in numbers 1-20.

[0334] Table 10 Formulation composition of the liquid crystal composition in Application Example 6

[0335]

[0336] Table 11 Formulation composition of the liquid crystal composition in Application Example 7

[0337]

[0338] Table 12 Formulation composition of the liquid crystal composition in Application Example 8

[0339]

[0340] Table 13 Test results of performance parameters of the liquid crystal compositions in Application Examples 6-8

[0341]

[0342] In summary, the liquid crystal compound represented by Formula I provided in the technical solution of this invention has a high clearing point, low dielectric loss, high dielectric tuning efficiency τ, and high quality factor η. Liquid crystal compositions containing this organic compound also have high clearing points, low dielectric loss, high dielectric tuning efficiency, and high quality factor η, and can be used to develop components and devices with high-frequency technology for microwave applications, particularly microwave phase-shifting devices, tunable filters, tunable metamaterial structures, and electronic beam-manipulated antennas (e.g., phase array antennas).

[0343] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions or improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. An isothiocyanate liquid crystal compound, characterized in that, The isothiocyanate liquid crystal compound is selected from at least one of the following compounds: Ⅰ-1-2、 Ⅰ-1-4、 Ⅰ-2-4、 Ⅰ-3-1、 Ⅰ-3-2、 Ⅰ-3-4、 Ⅰ-4-1、 Ⅰ-4-2、 Ⅰ-4-4、 Ⅰ-5-1、 Ⅰ-5-2、 Ⅰ-5-4 Among them, R 11 It is selected from alkyl, alkoxy, or alkenyl groups having 2-6 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentyl, cyclopentenyl, cyclobutyl, or cyclopropyl groups. Q 11 Choose from O or S.

2. A liquid crystal composition, characterized in that, It includes one or more isothiocyanate liquid crystal compounds as described in claim 1.

3. The liquid crystal composition according to claim 2, characterized in that, The isothiocyanate liquid crystal compound content in the liquid crystal composition is 0.1%-60% by mass percentage.

4. The liquid crystal composition according to claim 3, characterized in that, The liquid crystal composition further comprises at least one compound of formula (II): Formula (II) in, R3 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene. , Each independently selected , , or ; Z3 and Z4 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or -CH2CH2-; m2 represents 0, 1, or 2.

5. The liquid crystal composition according to claim 3, characterized in that, The liquid crystal composition further comprises at least one compound of formula (Ⅲ): Formula (III) in, R4 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more of these groups may have one or more non-attached -CH2- groups replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene. , Each independently selected , , or ; Z5 and Z6 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or -CH2CH2-; m3 represents 0, 1, or 2.

6. The liquid crystal composition according to claim 5, characterized in that, The liquid crystal composition further comprises at least one compound of formula (IV): Equation (Ⅳ) in, R5 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more of these groups may have one or more non-connected -CH2- replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene. , Each independently selected , , or ; Z7 and Z8 are each independently selected from single bonds, -C≡C-, -CH=CH-, -CF=CF-, or -CH2CH2-; m4 represents 0, 1, or 2.

7. The liquid crystal composition according to claim 5, characterized in that, The liquid crystal composition further comprises at least one compound of formula (V): Formula (V) in, R6 is selected from alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkenoxy groups having 2-10 carbon atoms; wherein any one or more unattached -CH2- groups may be replaced by cyclopentylene, cyclopentenylene, cyclobutylene, or cyclopropylene. , Each independently selected , , or ; Z a Z b Each is independently selected from a single bond, -C≡C-, -CH=CH-, -CF=CF-, or -CH2CH2-; m5 represents 0, 1, or 2.

8. The liquid crystal composition according to claim 3, characterized in that, The liquid crystal composition further comprises at least one compound of formula (VI): Formula (VI) in, and Each independently selected , or ;in One or more unconnected -CH2- can be replaced by -O-. The H atom in the middle can be replaced by F; R7 and R8 are each independently selected from alkyl groups having 1-10 carbon atoms, alkenyl groups having 2-10 carbon atoms, or alkynyl groups having 2-10 carbon atoms; Z c Selected from -CO-O-, -O-CO-, -CH=CH-, -C≡C- or single bonds; m6 represents 2, 3, or 4; When m6 represents 2, 3 or 4 Same or different, Z c Same or different.

9. A high-frequency component, characterized in that, It includes one or more liquid crystal compositions according to any one of claims 2-8.

10. The high-frequency component as described in claim 9, characterized in that, The high-frequency components are liquid crystal-based antenna elements, phase shifters, tunable filters, tunable metamaterial structures, matching networks, or varactor diodes.

11. A microwave antenna array, characterized in that, It includes one or more high-frequency components as described in claim 9 or 10.

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