An azo dye liquid crystal compound and a liquid crystal composition

Abstract

This invention discloses an azo dye liquid crystal compound, a liquid crystal composition containing the azo dye liquid crystal compound, and its applications. The azo dye liquid crystal compound has the structural formula shown in Formula I below. This dye liquid crystal compound exhibits a high dichroic ratio and good miscibility with the liquid crystal composition. The liquid crystal composition containing the dye liquid crystal compound shown in Formula I can be used to manufacture liquid crystal display elements or liquid crystal displays such as dimming films and dimming glasses.

Description

Technical Field

[0001] The present invention relates to the technical field of display materials, and in particular to an azo dye liquid crystal compound, a liquid crystal composition comprising the azo dye liquid crystal compound, and applications thereof in dimming films, dimming glasses, and liquid crystal display elements. Prior Art

[0002] With the rapid development of the electronics industry, the requirements for electronic device display technology are becoming increasingly stringent. In recent years, due to the thinness, low driving voltage and low power consumption of liquid crystal displays, they have been widely used in the field of lightweight and flat displays. Therefore, liquid crystal displays have become the mainstream display device.

[0003] Liquid crystal display panels are passive devices that don't emit light themselves. Their display technology uses a liquid crystal medium sandwiched between two parallel glass substrates. Voltage changes across the glass substrates alter the orientation of the liquid crystal molecules, which in turn control the brightness of light emitted by a backlight module to produce the desired image. However, most current LCD devices use polarizing plates, which significantly reduce light efficiency and, in turn, the performance of LCD technology.

[0004] In order to avoid the influence of polarizers on light utilization in liquid crystal display technology, host-guest liquid crystal devices have attracted widespread attention. Luminescent display can be achieved in a reflective device structure without a backlight source. The host-guest liquid crystal is a dichroic dye (guest) dissolved in liquid crystal (host). During the display process, the dye absorbs visible light of different wavelengths to make the liquid crystal device show different colors. The dichroic dye is usually rod-shaped, and visible light has different absorption effects in its long axis and short axis directions, so that the dye has light anisotropy. When the vibration direction of the incident light is consistent with the long axis direction of the dye molecule, the incident light is absorbed; conversely, when the vibration direction of the incident light is consistent with the short axis direction of the dye molecule, the incident light can be transmitted. When the liquid crystal molecules in the device change their orientation with the change of the electric field, the dye molecules are driven to change accordingly, and then the angle between the dye and the incident light also changes, and finally the device realizes the absorption and transmission of light. The commonly used dichroic dyes in the current state of the art are azo dyes and anthraquinone dyes. Azo dyes are widely used in liquid crystal displays (LCDs) due to their diverse color palette, rich colors, and high brightness. The application of these dyes in liquid crystals primarily involves introducing liquid crystal segments to alter the dye's molecular structure, thereby enabling the LCD to exhibit numerous optoelectronic properties. Further research into these properties will help improve the quality and performance of LCDs. However, the main drawbacks of azo dyes in the current state of the art are their low dichroic ratio and poor solubility in liquid crystal materials. Their solubility is generally 0.5 wt%, and their dichroic ratio is generally 3. The higher the dichroic ratio and solubility of azo dyes in liquid crystal media, the higher the contrast, better the display quality, and lower the power consumption of the LCD device. Therefore, developing an azo dye with a high dichroic ratio and high solubility is crucial for LCD technology. Summary of the Invention

[0005] The present invention provides an azo dye that solves the problems of low dichroic ratio and poor solubility in liquid crystal compositions of azo dyes in the prior art. Liquid crystal compositions containing the azo dye liquid crystal compound can be used to manufacture products such as dimming films, dimming glasses, and liquid crystal display elements.

[0006] In order to achieve the above-mentioned object of the invention, the present invention adopts the following technical solutions:

[0007] The present invention provides an azo dye liquid crystal compound, the general structural formula of the compound is shown in Formula I: I in, 、 、 、 Each independently represents a benzene ring or a naphthalene ring; L 1, L 2, L 3, L 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a haloalkyl group having 1 to 15 carbon atoms or a haloalkoxy group having 1 to 15 carbon atoms; R1, R2, R3, and R4 each independently represent a single bond or a chain alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the chain alkyl group are optionally substituted by halogen, and / or any one or more -CH2- in the chain alkyl group are optionally independently replaced by -C≡C-, -CH=CH-, 、 、 、 , ‑O‑, ‑S‑, ‑CO‑O‑, or ‑O‑CO‑, substituted in such a way that the O or S atoms are not directly bonded to each other; Z 1, Z 2 each independently represents -N-, -O- or -S-; When Z 1 represents -N-, n represents 1; when Z 1 represents -O- or -S-, n represents 0; When Z 2 represents -N-, m represents 1; when Z 2 represents -O- or -S-, m represents 0. Simple diagram description

[0008] FIG1 shows transmittance curves of the dye liquid crystal compounds D1 and I-1-1-5 at different wavelengths at 0V and 10V in the mother liquid crystal 1. FIG1 shows transmittance curves of the dye liquid crystal compounds D1 and I-1-1-5 at different wavelengths at 0V and 10V.

[0009] FIG2 shows the dichroic ratios of the dye liquid crystal compounds D1 and I-1-1-5 at different wavelengths in the mother liquid crystal 1. Implementation Method

[0010] The present invention provides an azo dye liquid crystal compound, the general structural formula of the compound is shown in Formula I: I in, 、 、 、 Each independently represents a benzene ring or a naphthalene ring; L 1, L 2, L 3, L 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a haloalkyl group having 1 to 15 carbon atoms or a haloalkoxy group having 1 to 15 carbon atoms; R1, R2, R3, and R4 each independently represent a single bond or a chain alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the chain alkyl group are optionally substituted by halogen, and / or any one or more -CH2- in the chain alkyl group are optionally independently replaced by -C≡C-, -CH=CH-, 、 、 、 , ‑O‑, ‑S‑, ‑CO‑O‑, or ‑O‑CO‑, substituted in such a way that the O or S atoms are not directly bonded to each other; Z 1, Z 2 each independently represents -N-, -O- or -S-; When Z 1 represents -N-, n represents 1; when Z 1 represents -O- or -S-, n represents 0; When Z 2 represents -N-, m represents 1; when Z 2 represents -O- or -S-, m represents 0.

[0011] The azo dye liquid crystal compound of the present invention is preferably selected from the group consisting of compounds represented by the following formulas I-1 to I-3. I-1 I-2 I-3 in, 、 Each independently represents a benzene ring or a naphthalene ring; L 1, L 2, L 3, L 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1-15 carbon atoms, a haloalkyl group having 1-15 carbon atoms, or a haloalkoxy group having 1-15 carbon atoms; R1, R2, R3, and R4 each independently represent a single bond or a chain alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the chain alkyl group are optionally substituted by halogen, and / or any one or more -CH2- in the chain alkyl group are optionally independently replaced by -C≡C-, -CH=CH-, 、 、 、 , ‑O‑, ‑S‑, ‑CO‑O‑, or ‑O‑CO‑, substituted in such a way that the O or S atoms are not directly bonded to each other; Z 1, Z 2 each independently represents -N-, -O- or -S-; When Z 1 represents -N-, n represents 1; when Z 1 represents -O- or -S-, n represents 0; When Z 2 represents -N-, m represents 1; when Z 2 represents -O- or -S-, m represents 0.

[0012] The azo dye liquid crystal compound of the present invention is preferably selected from the group consisting of the compounds represented by the aforementioned formulas I-1 to I-3, I-1-1 I-1-2 I-1-3 I-2-1 I-3-1 in, L 1, L 2, L 3, L 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a haloalkyl group having 1 to 15 carbon atoms or a haloalkoxy group having 1 to 15 carbon atoms; R1, R2, R3, and R4 each independently represent a single bond or a chain alkyl group having 1 to 15 carbon atoms, and one or more H atoms in the chain alkyl group are optionally substituted by halogen, and / or any one or more -CH2- in the chain alkyl group are optionally independently replaced by -C≡C-, -CH=CH-, 、 、 、 , ‑O‑, ‑S‑, ‑CO‑O‑, or ‑O‑CO‑, substituted in such a way that the O or S atoms are not directly bonded to each other; Z 1, Z 2 each independently represents -N-, -O- or -S-; When Z 1 represents -N-, n represents 1; when Z 1 represents -O- or -S-, n represents 0; When Z 2 represents -N-, m represents 1; when Z 2 represents -O- or -S-, m represents 0.

[0013] The azo dye liquid crystal compound of the present invention is preferably selected from any one or any combination of the compounds represented by the aforementioned formulas I-1-1 to I-2-1, 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 I-1-1-12 I-1-1-13 I-1-1-14 I-1-1-15 I-1-1-16 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-2-1-1 I-2-1-2 I-2-1-3 I-2-1-4。

[0014] The present invention provides a liquid crystal composition comprising at least one of the aforementioned azo dye liquid crystal compounds and at least one liquid crystal compound having neutral dielectric anisotropy.

[0015] The liquid crystal composition of the present invention, preferably, comprises one or more compounds represented by formula II, II in, R 5 and R 6 each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, a linear or branched alkoxy group having 1 to 15 carbon atoms, a linear or branched alkenyl group having 2 to 15 carbon atoms, or a linear or branched alkenyloxy group having 3 to 15 carbon atoms; Z 3 represents a single bond, -C≡C-, -CH 2-O- or -COO-; r, e each independently represent 1, 2 or 3; 、 Each independently expresses 、 、 、 、 or ; and when r represents 2 or 3, two or three Optional same or different.

[0016] In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula II is selected from the group consisting of compounds represented by the following formulas II-1 to II-32, 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 II-19 II-20 II-21 II-22 II-23 II-24 II-25 II-26 II-27 II-28 II-29 II-30 II-31 II-32.

[0017] The liquid crystal composition of the present invention, preferably, further comprises one or more compounds represented by formula III, III in, R 7 represents a linear or branched alkyl group having 1 to 15 carbon atoms, a linear or branched alkoxy group having 1 to 15 carbon atoms, a linear or branched alkenyl group having 2 to 15 carbon atoms, or a linear or branched alkenyloxy group having 3 to 15 carbon atoms; R 8 represents -F, -C≡C, -CF 3, -OCF 3 or CN; Z 4 represents a single bond, -CF 2O-, -CH 2O- or -COO-; a, b each independently represent 1 or 2; 、 Each independently expresses 、 、 、 、 or ; and when a or b represents 2, the two 、 are independently the same or different.

[0018] In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula III is selected from the group consisting of compounds represented by the following formulae III-1 to III-38, 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 III-19 III-20 III-21 III-22 III-23 III-24 III-25 III-26 III-27 III-28 III-29 III-30 III-31 III-32 III-33 III-34 III-35 III-36 III-37 III-38 wherein R7 represents a linear or branched alkyl group having 1 to 15 carbon atoms, a linear or branched alkoxy group having 1 to 15 carbon atoms, a linear or branched alkenyl group having 2 to 15 carbon atoms, or a linear or branched alkenyloxy group having 3 to 15 carbon atoms.

[0019] The liquid crystal composition of the present invention, preferably, further comprises one or more compounds represented by formula IV, IV in, R9 and R10 each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, a linear or branched alkoxy group having 1 to 15 carbon atoms, a linear or branched alkenyl group having 2 to 15 carbon atoms, or a linear or branched alkenyloxy group having 3 to 15 carbon atoms; Z 5 represents a single bond, -CF 2O-, -CH 2O-, -CH=CH-, -C≡C- or -CH 2CH 2-; c, d each independently represent 0, 1 or 2; 、 Each independently expresses 、 、 、 、 、 or ; and when c or d represents 2, the two 、 Each independently may be the same or different.

[0020] In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula IV is selected from the group consisting of compounds represented by the following formulas IV-1 to IV-11, IV-1 IV-2 IV-3 IV-4 IV-5 IV-6 IV-7 IV-8 IV-9 IV-10 IV-11 wherein R9 and R10 each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, a linear or branched alkoxy group having 1 to 15 carbon atoms, a linear or branched alkenyl group having 2 to 15 carbon atoms, or a linear or branched alkenyloxy group having 3 to 15 carbon atoms.

[0021] In the liquid crystal composition of the present invention, preferably, the mass content of the aforementioned azo dye liquid crystal compound is added on the basis of 100% of the total mass content of the liquid crystal composition, and the added amount is 0.3-5%.

[0022] The present invention also provides a dimming film, which comprises at least one of the aforementioned azo dye liquid crystal compounds or at least one of the aforementioned liquid crystal compositions.

[0023] The present invention also provides a dimming glass, which comprises at least one of the aforementioned azo dye liquid crystal compounds or at least one of the aforementioned liquid crystal compositions.

[0024] The present invention also provides a liquid crystal display element, comprising at least one of the aforementioned azo dye liquid crystal compounds, or at least one of the aforementioned liquid crystal compositions; preferably, the liquid crystal display element is a host-guest liquid crystal display element.

[0025] The present invention also provides a liquid crystal display, comprising at least one of the aforementioned azo dye liquid crystal compounds, or at least one of the aforementioned liquid crystal compositions; preferably, the liquid crystal display is a host-guest liquid crystal display.

[0026] [Beneficial effects:]

[0027] 1. The azo dye provided by the present invention is red, has a maximum absorption wavelength range of 480 nm to 550 nm, has high photostability, a high dichroic ratio, and is highly compatible with liquid crystal materials (the dichroic dye is added to the liquid crystal composition in an amount of 0.5-5%, preferably 0.5-3.5%, and does not precipitate after being placed in a -20°C glove box for 10 days). The biphenyl structure placed in the middle of the compound structure has a better aspect ratio and a better linear relationship than the biphenyl structure placed near the ends. At the same time, the molecular structure of the liquid crystal compound is more regular. Therefore, the azo dye liquid crystal compound of the present invention has a better dichroic ratio and better low-temperature miscibility.

[0028] 2. The liquid crystal composition containing the azo dye of formula I provided by the present invention displays colorless when powered in different mother liquid crystals, has high light transmittance (visible light transmittance reaches 26%-33% under 10 V power supply conditions), displays red after power is removed, and has low light transmittance (visible light transmittance reaches 2.6%-3.6% under 0 V power supply conditions), and can be used to manufacture products such as dimming films, dimming glasses, liquid crystal display elements or liquid crystal displays. [Example]

[0029] To more clearly illustrate the present invention, the present invention is further described below in conjunction with preferred embodiments. Those skilled in the art should understand that the detailed description below is illustrative and non-restrictive, and should not be used to limit the scope of protection of the present invention. The examples and comparative examples in this specification are provided to more fully illustrate this specification to those skilled in the art. The examples and comparative examples in this specification can be modified into various different forms, and the scope of protection of the present invention should not be limited solely to the examples and comparative examples detailed below.

[0030] The method for preparing the compound represented by the aforementioned formula I of the present invention preferably adopts the following synthetic route, and other similar structures can also be prepared using this method.

[0031] Example 1

[0032] This embodiment provides a liquid crystal compound I-1-1-1, the structure and synthesis route of which are as follows: I-1-1-1

[0033] Step 1

[0034] N-toluidine (25 g, 0.234 mmol), bromohexane (58 g, 0.35 mmol), and potassium carbonate (97 g, 0.7 mmol) were added to a 500 ml three-necked flask, and 200 ml of DMF was added to the flask. After nitrogen replacement three times, the temperature was raised to 110 ° C and heated for 24 hours, then cooled to room temperature. The reaction solution was poured into 500 ml of ice water, extracted with ethyl acetate, dried, and concentrated to obtain intermediate 1 (25 g, 56%) as a yellow oil.

[0035] Step 2

[0036] Solution A: Add 200 ml of water, 25 ml of 3N hydrochloric acid, and p-bromoaniline (25 g, 0.132 mmol) to a 500 ml three-necked flask. Cool the system to 0 degrees Celsius, then add sodium nitrite (9.3 g, 0.134 mmol) and stir at this temperature for 1 hour.

[0037] Solution B: Add 100 ml of ethanol, 50 ml of water, and intermediate 1 (25 g, 0.132 mmol) to a 1 L three-necked flask and cool the system to 0 °C.

[0038] Solution A was added to solution B within 20 min, and the temperature was kept at 0 degrees Celsius and stirred for 1 hour. Subsequently, 500 ml of water and 300 ml of ethyl acetate were added to the system, and the liquids were separated after stirring. The reaction liquid was extracted with ethyl acetate, and the organic phase was dried, concentrated, and purified by silica gel column (petroleum ether: ethyl acetate 15:1) to obtain intermediate 2 (13 g, 25%).

[0039] Step 3

[0040] Intermediate 2 (20 g, 0.051 mmol), boranediol (6.5 g, 0.0254 mmol), potassium carbonate (8.4 g, 0.061 mmol), tetrakistriphenylphosphine palladium (0.03 g, 0.00002 mmol), and toluene (30 ml) were added to a 250 ml three-necked flask, protected by nitrogen, heated under reflux for 3 hours, cooled to room temperature, and 100 ml of water was added to the reaction mixture. The liquid was separated, and the toluene phase was passed through a silica gel column and concentrated to obtain 15 g of an oily substance. The mixture was coated with silica gel and mixed, and then passed through a silica gel column (petroleum ether: ethyl acetate = 20:1) to obtain I-1-1-1 (4.3 g, 51%). MS (m / z) (M+): 588.39

[0041] Example 2

[0042] This embodiment provides a liquid crystal compound I-1-1-2, whose structural formula is as follows: I-1-1-2

[0043] The synthetic route of this compound is as follows:

[0044] The specific synthesis method is the same as that of compound Example 1, except that N-toluidine is replaced by aniline, and the final product I-1-1-2 (3.5 g, yield 38%) is obtained, MS (m / z) (M+): 728.55.

[0045] Example 3

[0046] This embodiment provides a liquid crystal compound I-1-1-5, whose structural formula is as follows: I-1-1-5

[0047] The synthetic route of this compound is as follows:

[0048] The specific synthesis method is the same as that of compound Example 1, except that p-bromoaniline is replaced by o-fluoro-p-bromoaniline, and the final product I-1-1-5 (2.4 g, yield 33%) is obtained, MS (m / z) (M+): 624.38.

[0049] Example 4

[0050] This embodiment provides a liquid crystal compound I-1-1-6, whose structural formula is as follows: I-1-1-6

[0051] The synthetic route of this compound is as follows:

[0052] The specific synthesis method is the same as that of compound Example 1, except that p-bromoaniline is replaced by o-fluoro-p-bromoaniline, and N-toluidine is replaced by aniline, and the final product I-1-1-6 (3.9 g, yield 33%) is obtained, MS (m / z) (M+): 764.53.

[0053] Example 5

[0054] This embodiment provides a liquid crystal compound I-1-1-8, whose structural formula is as follows: I-1-1-8

[0055] The synthetic route of this compound is as follows:

[0056] The specific synthesis method is the same as that of compound Example 1, except that bromohexane is replaced by ethyl bromovalerate, and the final product I-1-1-8 (5.1 g, yield 42%) is obtained, MS (m / z) (M+): 676.37.

[0057] Example 6

[0058] This embodiment provides a liquid crystal compound I-1-1-12, whose structural formula is as follows: I-1-1-12

[0059] The synthetic route of this compound is as follows:

[0060] The specific synthesis method is the same as that of compound Example 1, except that bromohexane is replaced by ethyl bromovalerate and p-bromoaniline is replaced by o-fluoro-p-bromoaniline, and the final product I-1-1-12 (4.5 g, yield 47%) is obtained, MS (m / z) (M+): 712.35.

[0061] Example 7

[0062] This embodiment provides a liquid crystal compound I-1-1-13, whose structural formula is as follows: I-1-1-13

[0063] The synthetic route of this compound is as follows:

[0064] Step 1

[0065] Phenol (20 g, 0.21 mmol), ethyl bromovalerate (48 g, 0.23 mmol), potassium carbonate (43 g, 0.315 mmol), and DMF (200 ml) were added to 250 ml of the mixture and the temperature was raised to 120 degrees Celsius for reaction. After 4 hours of reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, dried, and concentrated to obtain a crude yellow oil, which was purified by silica gel column with ethyl acetate: petroleum ether (10:1) to obtain intermediate 1 (44 g, 94%).

[0066] Step 2

[0067] Solution A: Add 200 ml of water, 25 ml of 3N hydrochloric acid, and p-bromo-o-fluoroaniline (15 g, 0.08 mmol) to a 500 ml three-necked flask. Cool the system to 0 degrees Celsius, then add sodium nitrite (5.5 g, 0.08 mmol) and stir at this temperature for 1 hour.

[0068] Solution B: Add 100 ml of ethanol, 50 ml of water, and intermediate 1 (17.7 g, 0.08 mmol) to a 1 L three-necked flask and cool the system to 0 °C.

[0069] Solution A was added to solution B within 20 min, and the temperature was kept at 0 degrees Celsius and stirred for 1 hour. Subsequently, 500 ml of water and 300 ml of ethyl acetate were added to the system, and the liquids were separated after stirring. The reaction liquid was extracted with ethyl acetate, and the organic phase was dried, concentrated, and purified by silica gel column (petroleum ether: ethyl acetate 15:1) to obtain intermediate 2 (18 g, 33%).

[0070] Step 3

[0071] Intermediate 2 (18 g, 0.026 mmol), boranediol (3.3 g, 0.013 mmol), potassium carbonate (11 g, 0.078 mmol), tetrakistriphenylphosphine palladium (0.015 g, 0.000013 mmol), and toluene (30 ml) were added to a 250 ml three-necked flask, protected by nitrogen, heated under reflux for 3 hours, cooled to room temperature, and 100 ml of water was added to the reaction mixture. The liquid was separated, and the toluene phase was passed through a silica gel column and concentrated to obtain 15 g of an oily substance. The mixture was coated with silica gel and mixed, and then passed through a silica gel column (petroleum ether: ethyl acetate = 20:1) to obtain I-1-1-13 (5.2 g, 41%). MS (m / z) (M+): 686.29

[0072] Example 8

[0073] This embodiment provides a liquid crystal compound I-1-1-9, whose structural formula is as follows: I-1-1-9

[0074] The synthetic route of this compound is as follows:

[0075] The specific synthesis method is the same as that of compound Example 7, except that o-fluoro-p-bromoaniline is replaced by p-bromoaniline, and the final product I-1-1-9 (6.3 g, yield 56%) is obtained, MS (m / z) (M+): 650.31.

[0076] Example 9

[0077] This embodiment provides a liquid crystal compound I-1-1-15, whose structural formula is as follows: I-1-1-15

[0078] The synthetic route of this compound is as follows:

[0079] The specific synthesis method is the same as that of compound Example 7, except that ethyl bromovalerate is used instead of bromohexane, and the final product I-1-9 (6.2 g, yield 58%) is obtained, MS (m / z) (M+): 598.31.

[0080] Example 10

[0081] This embodiment provides a liquid crystal compound I-2-1-1, whose structural formula is as follows: I-2-1-1

[0082] The synthetic route of this compound is as follows:

[0083] The specific synthesis method is the same as that of compound Example 1, except that 1-naphthylamine is replaced by 4-bromo-1-naphthylamine, and the intermediate 2 of this batch of compounds is coupled with the intermediate 2 of Example 1 according to the reaction conditions of Example 1 to finally obtain the product I-2-1-1 (2.3 g, yield 25%), MS (m / z) (M+): 638.14.

[0084] Example 11

[0085] This embodiment provides a liquid crystal compound I-2-1-2, whose structural formula is as follows I-2-1-2

[0086] The synthetic route of this compound is as follows:

[0087] The specific synthesis method is the same as that of compound Example 2, except that p-bromoaniline is replaced by 4-bromo-1-naphthylamine. The intermediate 2 of this batch of compounds is coupled with the intermediate 2 of Example 2 according to the reaction conditions of Example 1 to finally obtain the product I-2-1-2 (2.1 g, yield 23%), MS (m / z) (M+): 778.57.

[0088] Table 1 Corresponding codes of ring structures Ring structure Corresponding code C P L G Gi Y U K A D Sa Sb Sc

[0089] Table 2 Corresponding codes of terminal groups and linking groups End groups and linking groups Corresponding code C nH 2n+1- n- C nH 2n+1O- nO- -CF 3 -T -OCF 3 -OT -CF2O- -Q- -CH2O- -O- -O- -B- -F -F -CN -CN -CH 2CH 2- -E- -CH=CH- -V- -C≡C- -W- -COO- -Z- -CH=CH-C nH 2n+1 -Vn Cp- Cpr- Cpr1-

[0090] Example: , its code is CC-Cp-V1; , whose code is PGP- Cpr1-2; , whose code is CPY-2-O2; , its code is CCY-3-O2; , whose code is COY-3-O2; , whose code is CCOY-3-O2; , its code is Sb-CpO-O4; , its code is Sc-CpO-O4; , whose code is CCU- 3-F; , whose code is PGU- 3-F; , its code is CCPU- 3-F; , whose code is CPGU- 3-OT; , whose code is DGUQU-4-F; , whose code is PGUQU-3-​​F; , its code is PPGU-Cp-F. [Application Examples]

[0091] Comparative Dye Liquid Crystal Compounds: D1 D2 D3

[0092] Table 3 Matrix Liquid Crystal 1 Structure Ratio III PZG-2-CN 1 III PZG-3-CN 10 III CCPU-3-F 5 III PZU-2-CN 3 III PZU-3-CN 4 III CU-3-CN 5 II CC-3-V 7 II CCZPC-3-2 2 II CCZPC-3-3 22 III CDU-2-F 2 III CDU-3-F 6 III CDU-5-F 6 III CCPU-2-F k 9 III CCGU-3-F 2 III PGUQU-3-F 5 III PGUQU-4-F 5 III PGUQU-5-F 6

[0093] Table 4 Mother Liquid Crystal 2 structure Proportion III CC-3-5 10 IV CPY-3-O2 5 IV CCOY-3-O2 27 IV CCOY-3-O2 4 IV CCY-2-O2 8 IV CCY-4-O2 2 IV CPY-2-O2 11 IV CY-V-O2 8 IV YZY-2O-O2 13 IV PYQY-2-3 3 IV PTY-3-O2 9

[0094] Table 5 Mother Liquid Crystal 3 structure Proportion IV CCOY-3-O2 30 II CCP-V-1 11 II CC-3-V 16.5 IV CY-3-O2 7.5 IV CCY-3-O2 7.47 IV CCY-2-O2 2 IV CPY-2-O2 10 IV CY-V-O2 6 IV YZY-2O-O2 9 IV PYQY-2-3 0.5 IV PTY-3-O2 0.03

[0095] Table 6 Mother Liquid Crystal 4 structure Proportion IV CCOY-3-O2 2 IV CCOY-5-O2 14 II CCP-V-1 24.5 II CC-3-V 10.5 IV CCY-3-O2 9 IV COY-3-O2 8 IV CCOY-2-O2 2 IV CLY-3-O2 9 IV CCOY-2-O4 6 IV CCOY-3-O4 9 IV CCOY-4-O4 6

[0096] Dichroic contrast test

[0097] In order to be closer to the actual working conditions of the dye, I-1-1-5 dye was added to the mother liquid crystal 1 as a test sample. At the same time, D1 dye was added to the same mother liquid crystal as a control sample. The addition amount of I-1-1-5 and D1 was 0.5%. They were heated and stirred at 120℃ for 1h, and then spotted using a TN-7.0 test box. The transmittance spectrum of 400-800nm ​​was tested at 0V and 10V voltages of DMS, and the transmittance at 0V and 10V at each wavelength was obtained. It can be seen from Figure 1 that the maximum absorption wavelengths of D1 and I-1-1-5 are between 500~520nm, and the absorption of I-1-1-5 at 0V is significantly lower than that of D1. Dichroic contrast = transmittance at 10V / transmittance at 0V, to calculate the dichroic contrast at each wavelength. As shown in Figure 2, at a wavelength of 500nm, the dichroic ratio of I-1-1-5 is 10, and the dichroic ratio of D1 is 3.15. The dichroic ratio of I-1-1-5 is significantly higher than that of D1.

[0098] Similarly, test the dichroic ratios of D2, D3, I-1-1-1, I-1-1-2, I-1-1-5, I-1-1-6, I-1-1-8, I-1-1-9, I-1-1-12, I-1-1-13, I-1-1-15, I-2-1-1, and I-2-1-2 in the mother liquid crystal 1; and the dichroic ratios of D1, D2, D3, I-1-1-1, I-1-1-2, I-1-1-5, I-1-1-6, I-1-1-8, I-1-1-9, I-1-1-12, I-1-1-13, I-1-1-15, I-2-1-1, and I-2-1-2 in the mother liquid crystals 2, 3, and 4. The specific data are as follows:

[0099] Table 7 Dichroic ratio data of different matrix liquid crystals Dye compounds Two-color ratio Mother liquid crystal 1 Mother LCD 2 Mother LCD 3 Mother LCD 4 D1 3.15 3.35 3.31 3.61 D2 3.6 3.8 3.51 3.58 D3 3.63 3.66 3.38 3.72 I-1-1-1 8.5 9.2 8.6 8.9 I-1-1-2 9.7 8.7 9.3 8.8 I-1-1-5 10.0 9.5 9.7 9.3 I-1-1-6 9.3 8.8 9.2 9.4 I-1-1-8 10.3 9.7 9.8 9.8 I-1-1-9 9.4 10.2 9.6 9.4 I-1-1-12 9.2 8.7 9.1 8.9 I-1-1-13 8.7 8.6 8.6 8.7 I-1-1-15 8.6 8.4 8.7 9.1 I-2-1-1 9.6 9.8 9.5 9.4 I-2-1-2 9.2 9.3 9.3 9.4

[0100] As shown in Table 7, the dichroic ratio of the azo dye of Formula I of the present invention in the matrix liquid crystal is superior to that of the control samples D1, D2, and D3. This means that the contrast of the liquid crystal composition containing the azo dye of Formula I in the matrix liquid crystal 1 is significantly improved compared to the control sample, making it more suitable for the manufacture of products such as dimming films, dimming glass, liquid crystal display devices, or liquid crystal displays.

[0101] Solubility test

[0102] D1, D2, D3, I-1-1-1, I-1-1-2, I-1-1-5, I-1-1-6, I-1-1-8, I-1-1-9, I-1-1-12, I-1-1-13, I-1-1-15, I-2-1-1, and I-2-1-2 were added to different mother liquid crystals at different concentrations (0.5-5wt%), mixed and stirred evenly in a glass bottle, and stored at -20°C. Whether there was crystal precipitation was observed every day. The results are shown in the following table:

[0103] Table 8 Low temperature experimental data in parent liquid crystal 1 concentration(%) serial number 0.5 0.8 1 1.5 2 2.5 3 3.5 4 4.5 5 D1 ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <7d <6d <3d <2d <1d D2 ≥10 days ≥10 days ≥10 days <9d <9d <8d <7d <6d <2d <1d <1d D3 ≥10 days ≥10 days ≥10 days <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-5<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-6<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"><9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-8<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-9<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-12<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-13<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-15<h2 style=";text-align:left;direction:ltr"> ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <8d <6d I-2-1-1 ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <6d I-2-1-2 ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <6d

[0104] Table 9 Low temperature experimental data in parent liquid crystal 2 Concentration (%) No. 0.5 0.8 1 1.5 2 2.5 3 3.5 4 4.5 5 D1 ≥10 days<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <3d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> D2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> D3<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-5<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-6<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-8<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-9<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-12<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-13<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-15<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-2-1-1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-2-1-2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <6d

[0105] Table 10 Low temperature experimental data in parent liquid crystal 3 concentration(%) serial number 0.5 0.8 1 1.5 2 2.5 3 3.5 4 4.5 5 D1 ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <7d <6d <3d <2d <1d D2 ≥10 days ≥10 days ≥10 days <9d <9d <8d <7d <6d <2d <1d <1d D3 ≥10 days ≥10 days ≥10 days ≥10 days <h2 style=";text-align:left;direction:ltr"><9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-5<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-6<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d <8d <6d I-1-1-8 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <10d <10d <9d <8d I-1-1-9 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <8d <6d I-1-1-12 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥9d <8d <6d I-1-1-13 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <10d <10d <10d <10d I-1-1-15 ≥10d ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <8d <6d I-2-1-1 ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <9d <8d <6d I-2-1-2 ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days ≥10 days <10d <9d <8d <6d

[0106] Table 11 Low temperature experimental data in parent liquid crystal 4 Concentration (%) No. 0.5 0.8 1 1.5 2 2.5 3 3.5 4 4.5 5 D1 ≥10 days <h2 style=";text-align:left;direction:ltr">≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <3d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> D2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> D3<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <7d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <2d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <1d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-5<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-6<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-8<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <9d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> I-1-1-9<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ≥10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <10d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <8d<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> <6d<h2 style=";text-align:left;direction:ltr"> I-1-1-12 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <9d <8d <6d I-1-1-13 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <10d <10d <10d <10d I-1-1-15 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <10d <8d <6d I-2-1-1 ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d ≥10d <10d <9d <8d <6d I-2-1-2 ≥10d ≥10d ≥10d ≥10 days ≥10 days ≥10 days <10d <10d <9d <8d <6d

[0107] As can be seen from Tables 8-11, the azo dye liquid crystal compound represented by Formula I of the present invention has significantly better low-temperature solubility in liquid crystal materials than the comparative dye compound, meeting the requirements for long-term use at low temperatures after manufacturing products such as dimming films, dimming glasses, liquid crystal display elements, or liquid crystal displays.

[0108] The present invention can also have many other embodiments. Without departing from the spirit and essence of the present invention, technicians familiar with the field can make various corresponding changes and modifications based on the present invention, but these corresponding changes and modifications should fall within the scope of the patent application attached to the present invention.

[0109] none

Claims

1. An azo dye liquid crystal compound, with a structure as shown in Formula I-1-1-5, I-1-1-5.

2. A liquid crystal composition comprising at least one azo dye liquid crystal compound as described in claim 1, and at least one liquid crystal compound having neutral dielectric anisotropy.

3. The liquid crystal composition according to claim 2, further comprising one or more compounds of formula II, wherein R5 and R6 each independently represent a straight-chain alkyl or branched alkyl group having 1-15 carbon atoms, a straight-chain alkoxy or branched alkoxy group having 1-15 carbon atoms, an alkenyl straight-chain or branched alkenyl group having 2-15 carbon atoms, or a straight-chain alkenyl or branched alkenyl group having 3-15 carbon atoms; Z3 represents a single bond, -C≡C-, -CH2-O-, or -COO-; r and e each independently represent 1, 2, or 3; and each independently represent , , , , , or ; and when r represents 2 or 3, the two or three may be the same or different.

4. The liquid crystal composition according to claim 2, further comprising one or more compounds of formula III, wherein, R7 represents a straight-chain alkyl or branched alkyl group with 1-15 carbon atoms, a straight-chain alkoxy or branched alkoxy group with 1-15 carbon atoms, a straight-chain alkenyl or branched alkenyl group with 2-15 carbon atoms, or a straight-chain alkenyl or branched alkenyl group with 3-15 carbon atoms; R8 represents -F, -C≡C, -CF3, -OCF3, or CN; Z4 represents a single bond, -CF2O-, -CH2O-, or -COO-; a and b each independently represent 1 or 2; and each independently represent , , , , or; and when a or b represents 2, the two and each independently are the same or different.

5. The liquid crystal composition according to claim 2, further comprising one or more compounds of formula IV, wherein IV, R9 and R10 each independently represent a straight-chain alkyl or branched-chain alkyl group with 1-15 carbon atoms, a straight-chain alkoxy or branched-chain alkoxy group with 1-15 carbon atoms, a straight-chain alkenyl or branched-chain alkenyl group with 2-15 carbon atoms, or a straight-chain alkenyl or branched-chain alkenyl group with 3-15 carbon atoms; Z5 represents a single bond, -CF2O-, -CH2O-, -CH=CH-, -C≡C-, or -CH2CH2-; c and d each independently represent 0, 1, or 2; and each independently represent , , , , , or; and when c or d represents 2, the two and can be the same or different independently.

6. The liquid crystal composition according to any one of claims 2-5, wherein the mass content of the azo dye liquid crystal compound is added on the basis of 100% of the total mass content of the liquid crystal composition, and the amount added is 0.3-5%.

7. A dimming film comprising at least one azo dye liquid crystal compound as described in claim 1, or at least one liquid crystal composition as described in any one of claims 2-5.

8. A liquid crystal display element comprising at least one azo dye liquid crystal compound as described in claim 1, or at least one liquid crystal composition as described in any one of claims 2-5.

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