CN117165303A - Liquid crystal compound, liquid crystal composition and liquid crystal display element - Google Patents
Liquid crystal compound, liquid crystal composition and liquid crystal display element Download PDFInfo
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
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- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a liquid crystal compound, the structural formula of the liquid crystal compound is shown as the following formula I,the liquid crystal compound has good low-temperature intersolubility and good performance in the aspect of ultraviolet resistance, and can effectivelyThe contrast ratio of the liquid crystal composition is improved. The invention also discloses a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display element or a liquid crystal display.
Description
Technical Field
The invention relates to the technical field of liquid crystal display. And more particularly, to a liquid crystal compound, a liquid crystal composition including the same, a liquid crystal display element, or a liquid crystal display.
Background
With the development of display technology, flat panel display devices such as liquid crystal display devices (Liquid Crystal Display, LCD) have been widely used in various consumer electronic products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and have become the mainstream of display devices, eventually replacing cathode ray tube displays, because of their advantages such as high image quality, power saving, thin body, and wide application range.
The liquid crystal display is classified into a TN (twisted nematic), an STN (super twisted nematic ), an IPS (in-plane switching), a VA (vertical alignment), and the like according to the type of display mode.
The liquid crystal display device comprises a liquid crystal material, wherein the liquid crystal material is a mixture of organic rod-shaped small molecular compounds which have liquid fluidity and crystal anisotropism at a certain temperature. The liquid crystal material is widely used in display devices such as electronic calculators, notebooks, automobile instruments, televisions and the like because of the characteristic of optical anisotropy and dielectric anisotropy. With the increasing range of applications of liquid crystal display devices, higher requirements are put on the operating temperature range of the devices to adapt to various severe operating environments, and in many cases, the liquid crystal mixture is required to operate in very low or very high temperature environments, especially in cold outdoor environments and high temperature environments, so that in order to ensure that the liquid crystal display device normally operates in severe environments, higher requirements are put on the liquid crystal material, and the liquid crystal compound is required to have good low-temperature intersolubility and a wider operating temperature range.
Liquid-crystalline media having good chemical and thermal stability, good stability to electric fields and electromagnetic radiation, suitable optical anisotropy, small rotational viscosity, good low-temperature miscibility and the like are currently in urgent need, and especially liquid crystals are usually used by mixing various components, and the direct mutual miscibility of the components is particularly important. Meanwhile, since the liquid crystal compounds generally have sensitivity to ultraviolet rays, conventional liquid crystal materials are usually matched with additives with an anti-UV function in order to avoid damage caused by ultraviolet rays, and the most widely used liquid crystal materials are fluorinated tetrabiphenyl compounds. The fluoro-tetrabiphenyl compound is used as an ultraviolet absorber most commonly used in the field of liquid crystal materials at present, has good physical and chemical stability and good UV tolerance, but has positive dielectric property, and after being added into a negative liquid crystal composition, the fluoro-tetrabiphenyl compound slows down the response of the liquid crystal composition, so that the development of a compound with good low-temperature intersolubility and good UV resistance is a technical problem to be solved urgently at present.
For improved low temperature miscibility and UV resistance, reference is made to the following
TW200611964A, TW200613529a describes compounds of tetrabiphenyl with improved UV stability, shown by the following formula:
CN107075374a describes compounds of pentabiphenyls with improved UV stability, in particular compounds with the following biphenyl structure:
CN107434973a describes compounds of biphenylnaphthalenes, in particular terphenylnaphthalenes, with improved UV stability:
the compounds provided by the above references all have the disadvantage that although the UV resistance of the liquid crystal is improved after addition to the liquid crystal composition, there is no significant effect on the improvement of the image quality, and the addition of some compounds also has an effect on the low temperature stability, unlike what we conventionally believe is that the less rigid structure, the more substituents are, the better the solubility, which may be related to various forces within or between the molecules, and a great deal of research is still required for this defect.
Along with the progress of technology, the requirements of human beings on the display are higher and higher, the images of the display are required to be clearer, the image quality is better, and the tailing phenomenon does not occur in the picture switching process. The contrast ratio (CR is the ratio of the brightness at the brightest point to the brightness at the darkest point on the screen) is highly related to the image quality, the higher the contrast ratio is, the clearer the image quality is, the more vivid the color is shown on the display, the richer the layering is, and the contrast ratio of the conventional liquid crystal display is generally greater than 1000:1.
CR＝Tr Bright /Tr Dark and dark
Tr Dark and dark ∝1/S LC ；S LC ＝{(n e +n o ) 2 *△n 2 }/K ave ；K ave ＝(K 11 +K 22 +K 33 )/3
As can be seen from the definition of contrast, the method for improving contrast has two main aspects: on the one hand, the brightness of the display in the bright state is improved, and on the other hand, the brightness in the dark state is reduced, namely, the bright state is brighter and the dark state is darker. However, in the conventional development process, the contrast ratio is not improved by improving the brightness of the bright state, because the brightness of the bright state is mainly affected by the transmittance, and the transmittance is mainly affected by the larger the phase retardation amount Δnd of the liquid crystal cell, the larger the transmittance is, but the smaller the variable range of Δnd is due to the consideration of other factors such as color cast, viewing angle and the like, and the contribution to improving the contrast ratio is limited. Therefore, decreasing the dark state brightness is a main improvement direction for increasing the contrast ratio, and is affected by the alignment state of the liquid crystal, the liquid crystal display will have a certain light leakage in the dark state, i.e. the dark state brightness cannot reach absolute black, while slightly changing the dark state brightness will have a larger effect on the contrast ratio, so that the contrast ratio is increased by decreasing the dark state brightness, and the contrast ratio in the dark state needs to be increased starting from the elastic constant of the liquid crystal composition, and the increase of the elastic constant is beneficial to decreasing the dark state brightness. The color film and the liquid crystal material scatter light, and the optical principle shows that the polarization state of incident light is changed in the scattering process. Therefore, in the dark state, the polarized light transmitted through the lower polarizer is perpendicular to the transmission axis of the upper polarizer and cannot be transmitted, but when the polarized light is scattered in the liquid crystal and color film materials, part of the polarized state is changed, and components exist in the direction of the transmission axis of the upper polarizer, so that the upper polarizer is projected to form light leakage, and the contrast ratio is reduced. The stronger the scattering, the greater the contrast drop. Therefore, various panel manufacturers in the industry are actively searching for a method for reducing the dark state brightness, namely, how to increase the polarization degree of the polarizer, improve the alignment characteristic of the liquid crystal, develop a color resistance material with high contrast, develop a liquid crystal with high contrast, and the like. However, development of high contrast liquid crystal is currently under the spotlight of liquid crystal manufacturers, and for developing liquid crystal with high contrast, a liquid crystal compound or a liquid crystal composition having a larger elastic constant K, i.e., a liquid crystal composition having a smaller scattering coefficient, is required.
Therefore, developing a liquid crystal medium with high elastic constant K, good low-temperature intersolubility and good UV resistance is a technical problem to be solved.
Disclosure of Invention
The invention aims to solve the technical problem of providing a liquid crystal compound which has larger elastic constant K, smaller scattering coefficient and good low-temperature intersolubility and can effectively improve UV reliability.
The invention provides a liquid crystal compound, the structural formula of the liquid crystal compound is shown as the following formula I,
wherein,
L 1 represent F, cl or an alkyl group having 1 to 5 carbon atoms;
L 2 、L 3 、L 4 、L 5 、L 6 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
Another aspect of the present invention is to provide a liquid crystal composition having a large elastic constant K, a small scattering coefficient, good low-temperature intersolubility, and simultaneously being capable of effectively improving UV reliability.
In another aspect, the present invention provides a liquid crystal display device or a liquid crystal display, which comprises the liquid crystal compound and the liquid crystal composition, and has good reliability, wide working temperature range and high contrast ratio.
The beneficial effects of the invention are that
The liquid crystal compound has larger elastic constant K, smaller scattering coefficient and good low-temperature intersolubility, and can effectively improve UV reliability, and the dielectric property of the liquid crystal compound is close to neutral, so that the liquid crystal compound can be applied to liquid crystal compositions with positive polarity and liquid crystal compositions with negative polarity, and the response speed of the negative liquid crystal composition is not reduced after the conventional tetrabiphenyl and pentabiphenyl UV-resistant stabilizer is added into the negative liquid crystal composition. The liquid crystal composition containing the liquid crystal compound has larger elastic constant K, smaller scattering coefficient, good low-temperature intersolubility and good UV resistance, and the response speed of the composition is not reduced when the liquid crystal compound is applied to a liquid crystal composition with negative dielectric. Meanwhile, the liquid crystal display element or the liquid crystal display containing the liquid crystal compound and the liquid crystal composition has the advantages of high response speed, good reliability, wide working temperature range and high contrast ratio.
Drawings
FIG. 1 shows the MS mass spectrum of the compound of formula I-3-5-2;
FIG. 2 shows the MS mass spectrum of the compound of formula I-1-5-1.
Detailed Description
The first aspect of the invention provides a liquid crystal compound, the structural formula of the liquid crystal compound is shown as the following formula I,
wherein,
L 1 represent F, cl or an alkyl group having 1 to 5 carbon atoms;
L 2 、L 3 、L 4 、L 5 、L 6 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
The liquid crystal composition of the invention preferably comprises the formula IL in the compound shown 1 Is a-CH 3 monosubstituted liquid crystal compound, and the mass percentage is preferably 0.1-2%, more preferably 0.2-1%, and is added based on 100% of the total content of the liquid crystal composition.
The liquid crystal compound of the present invention is preferably a compound represented by the above formula I selected from the group consisting of compounds represented by the following formulas I-1 to I-4,
wherein,
L 2 、L 3 、L 4 、L 5 、L 6 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
The liquid crystal compound of the present invention is preferably a compound represented by the above formula I selected from the group consisting of compounds represented by the following formulas I-1-1 to I-4-5,
wherein,
L 2 、L 3 、L 4 、L 5 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
L 61 h, F, cl, C2-5 alkyl, C2-5 alkoxy, C2-5 alkenyl, or C3-5 alkenyloxy;
L 62 h, cl, C1-5 alkyl, C1-5 alkoxy, C2-5 alkenyl, or C3-5 alkenyloxy;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
The liquid crystal compound of the present invention is preferably a compound represented by the above formula I selected from the group consisting of compounds represented by the following formulas I-1-1-1 to I-4-5-2,
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in a second aspect, the present invention provides a liquid crystal composition comprising one or more compounds of formula I, wherein the addition is based on 100% of the total liquid crystal composition.
The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula II, one or more compounds represented by formula III,
wherein,
R 3 、R 4 、R 5 、R 6 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms;
each independently represents->Or->
The liquid crystal composition of the present invention is preferably one wherein the compound represented by the above formula II is selected from the group consisting of compounds represented by the following formulas II-1 to II-3,
wherein,
R 31 、R 41 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; preferably, represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
R 32 、R 42 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; preferably, represents an alkanyl group having 1 to 10 carbon atoms or an alkanyl group having 1 to 10 carbon atoms;
R 33 、R 43 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms.
The liquid crystal composition of the present invention preferably contains the compound represented by the following formula II-1-1, and the content by mass thereof is preferably 25% to 50%, more preferably 30% to 45%,
the liquid crystal composition of the present invention preferably contains the compound represented by the following formula II-3-1 or II-3-2, preferably in an amount of 1% to 15%, more preferably 5% to 10%,
the liquid crystal composition of the present invention is preferably one wherein the compound represented by the above formula III is selected from the group consisting of compounds represented by the following formulas III-1 to III-3,
wherein,
R 5 、R 6 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms.
The liquid-crystal composition of the invention may preferably further comprise one or more compounds of formula IV,
wherein,
R 7 、R 8 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms, wherein one or more of the non-bonded-CH 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
Z 1 represents a single bond, -CH 2 O or-CH 2 CH 2 -；
Each independently represents->/>Or->
m, n each independently represents 0, 1 or 2, and m, n do not simultaneously represent 2, when m or n represents 2, a plurality of Each may be the same or different.
The liquid crystal composition of the present invention is preferably one wherein the compound represented by the above formula IV is selected from the group consisting of compounds represented by the following formulas IV-1 to IV-14,
wherein,
R 7 、R 8 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms, wherein one or more of the non-bonded-CH 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene.
The liquid crystal composition of the present invention preferably further comprises one or more compounds of formula V,
wherein,
R 9 、R 10 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms, wherein one or more of the non-bonded-CH 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
x represents O, S or-CH 2 O-。
Further preferably, X represents S or-CH 2 O-。
Still more preferably, X represents S.
The liquid-crystal composition of the invention may preferably further comprise one or more compounds of formula VI,
wherein,
R 12 represents an alkanyl radical having 1 to 10 carbon atoms or an alkenyl radical having 2 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
R 13 representation F, CF 3 Or OCF (optical clear) 3 ；
Each independently represents-> Or->
r represents 1, 2 or 3, and when r represents 2 or 3, a plurality ofMay be the same or different.
The liquid crystal composition of the present invention is preferably one wherein the compound represented by the above formula VI is selected from the group consisting of compounds represented by the following formulas VI-1 to VI-21,
/>
wherein,
R 12 represents an alkanyl radical having 1 to 10 carbon atoms or an alkenyl radical having 2 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
R 13 representation F, CF 3 Or OCF (optical clear) 3 。
The liquid crystal composition of the present invention preferably further comprises one or more compounds of formula VII,
wherein,
R 14 represents an alkanyl radical having 1 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclopropylene or cyclobutylene;
t represents 0 or 1;
s represents 1, 2 or 3;
representation-> When s represents 2 or 3, a plurality of +.>May be the same or different.
The liquid crystal composition of the present invention is preferably one wherein the aforementioned compound represented by formula VII is selected from the group consisting of compounds represented by the following formulas VII-1 to VII-11,
/>
wherein,
R 14 represents an alkanyl radical having 1 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene.
Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl and the like.
Examples of the aforementioned chain alkoxy group having 1 to 10 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decyloxy and the like.
Examples of the alkenyl group having 2 to 10 carbon atoms include vinyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl and 3-hexenyl.
The liquid crystal composition of the present invention may preferably further comprise one or more polymerizable compounds.
In the liquid crystal composition of the present invention, the polymerizable group of the polymerizable compound is preferably a methacrylate or an acrylate.
The liquid crystal composition of the present invention, preferably, the aforementioned polymerizable compound is selected from the group consisting of compounds represented by the following formulas RM-1 to RM-5,
the liquid crystal composition of the present invention is preferably added in an amount of 0.1 to 0.5% by mass based on the total content of the liquid crystal composition of 100%.
Other additives such as UV stabilizer, antioxidant, radical scavenger, etc. may also be added to the liquid crystal composition of the present invention. The additives which may be mentioned are as follows:
/>
wherein u represents an alkylene group having 1 to 20 carbon atoms.
[ liquid Crystal display element or liquid Crystal display ]
The invention also provides a liquid crystal display element or a liquid crystal display comprising the liquid crystal compound or the liquid crystal composition.
Preferably, the liquid crystal display element may be an active matrix addressing liquid crystal display element or a liquid crystal display.
Preferably, the active matrix addressing liquid crystal display element is a VA-TFT, FFS-TFT or IPS-TFT liquid crystal display element.
The liquid crystal display element or the liquid crystal display of the invention comprises the liquid crystal compound and the liquid crystal composition, and can be used for developing the liquid crystal display element or the liquid crystal display with good reliability, wider working temperature range and higher contrast ratio.
Examples
The invention will be further illustrated by the following examples
Example 1
Preparation of Compound I-1-2-1
The preparation route is as follows:
the specific operation flow of the preparation is as follows:
preparation of intermediate a:
into a 3L three-necked flask, 0.5mol of [ 2-fluoro-4- (4-propylphenyl) phenyl ] boric acid, 0.5mol of 1-bromo-4-iodo-2-toluene, 0.6mol of anhydrous sodium carbonate, 1.0L of toluene, 0.5L of ethanol, 0.5L of water, nitrogen protection, stirring, adding 0.005mol of tetrakis (triphenylphosphine) palladium, and heating and refluxing for 6 hours. After the reaction, standing and separating, extracting the water phase with 0.5Lx2 toluene, combining the organic phases, washing with 0.5Lx2 water, passing through 200g of silica gel column, flushing the column with 0.5Lx3 toluene, combining the toluene solutions, spin-drying, heating and dissolving with 1 time petroleum ether of 2 times toluene, freezing for 4 hours at-20 ℃, filtering, recrystallizing once again according to the same method, and airing to obtain an intermediate A, wherein GC is 99.68%, and the yield is Y=68%.
Preparation of Compound I-1-2-1
Into a 1L three-necked flask, 0.1mol of intermediate A, 0.1mol of [4- (4-pentylphenyl) phenyl ] boric acid, 0.12mol of anhydrous sodium carbonate, 0.2L of toluene, 0.1L of ethanol, 0.1L of water, nitrogen protection, stirring, adding 0.001mol of tetrakis (triphenylphosphine) palladium, and heating and refluxing for reaction for 6 hours. After the reaction, the mixture was left to stand, the aqueous phase was extracted with 0.1 L.times.2 toluene, the organic phases were combined, washed with 0.1 L.times.2 water, passed through a 50g silica gel column, 0.1 L.times.3 toluene was washed, the toluene solution was combined, dried by spinning, and 3 times toluene was dissolved by heating, left to stand at room temperature for 4 hours, and suction filtration was performed, and recrystallized twice by the same method, and air-dried to give compound I-1-2-1, GC:99.82% and yield Y=62%.
According to the preparation method of the compound I-1-2-1, 1-bromo-4-iodo-2-toluene is changed into 1-bromo-2-ethyl-4-iodobenzene and 1-bromo-2-fluoro-4-iodobenzene, and the compounds I-2-2-1 and I-3-2-1 can be obtained
By referring to the preparation method of the compound I-1-2-2, the [ 2-fluoro-4- (4-propylphenyl) phenyl ] boric acid is changed into the [ 3-fluoro-4- (4-pentylphenyl) phenyl ] boric acid, and the compounds I-1-4-2, I-2-4-2 and I-3-4-2 can be obtained
Preparation of Compound I-1-5-1
The preparation route is as follows:
the specific operation flow of the preparation is as follows: into a 3L three-necked flask, 0.5mol of [4- (4-pentylphenyl) phenyl ] boric acid, 0.25mol of 1-bromo-4-iodo-2-toluene, 0.6mol of anhydrous sodium carbonate, 1.0L of toluene, 0.5L of ethanol, 0.5L of water and nitrogen were charged under the protection of nitrogen, and then, 0.005mol of tetrakis (triphenylphosphine) palladium was added thereto to carry out a reflux reaction under heating for 6 hours. After the reaction, standing and separating, extracting the aqueous phase with 0.5Lx2 toluene, mixing the organic phases, washing with 0.5Lx2 water, passing through 100g of silica gel column, flushing the column with 0.5Lx3 toluene, mixing the toluene solutions, spin-drying, heating and dissolving 3 times of toluene, standing at room temperature for 4 hours, filtering, recrystallizing twice according to the same method, and airing to obtain the compound I-1-5-1, wherein the GC is 99.82%, and the yield is Y=60%. The MS mass spectrum of the compound shown in the formula I-1-5-1 is shown in figure 2.
According to the preparation method of the compound I-1-5-1, 1-bromo-4-iodo-2-toluene is changed into 1-bromo-2-fluoro-4-iodobenzene and 1-bromo-4-iodo-2-ethylbenzene, and 1-bromo-2-chloro-4-iodobenzene, so that the compounds I-2-5-1, I-3-5-1 and I-4-5-1 can be obtained
According to the preparation method of the compound I-1-5-1, 1-bromo-4-iodo-2-toluene is changed into 1-bromo-2, 5-difluoro-4-iodobenzene and 1-bromo-4-iodo-2, 5-dimethylbenzene, and the compounds I-3-5-2 and I-1-5-4 can be obtained respectively
Wherein the MS mass spectrum of the compound shown in the formula I-3-5-2 is shown in figure 1.
According to the preparation method of the compound I-1-2-2, the intermediate A is used for converting [4- (4-pentylphenyl) phenyl ] boric acid into [ 3-fluoro-4- (4-propylphenyl) phenyl ] boric acid, so that the compound I-1-4-1 can be obtained
The monomer performance parameters are shown in table 1:
TABLE 1 monomer Performance parameters
/>
Comparative compound:
/>
in order to more clearly illustrate the invention, the invention is further described below in connection with preferred composition examples. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and that this invention is not limited to the details given herein.
In the invention, the preparation method is a conventional method unless specified otherwise, the raw materials used can be obtained from the disclosed commercial path unless specified otherwise, the percentages refer to mass percentages, the temperature is in degrees centigrade (DEG C), the liquid crystal compound is also a liquid crystal monomer, and the specific meanings and testing conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is tested by DSC quantification;
S-N represents the crystalline to nematic melting point (. Degree. C.) of the liquid crystal;
Δn represents optical anisotropy, Δn=n e -n o Wherein n is o Refractive index of ordinary ray, n e The refractive index of the extraordinary ray is 25+/-2 ℃ and is measured by an Abbe refractometer at 589 nm;
delta epsilon represents dielectric anisotropy, delta epsilon=epsilon ∥ -ε ⊥ Wherein ε is ∥ For dielectric constant parallel to the molecular axis ε ⊥ For the dielectric constant perpendicular to the molecular axis, the test conditions are 25+/-0.5 ℃ and 20-micrometer parallel boxes, INSTEC, ALCT-IR1 test;
γ 1 the rotational viscosity (mPas) was shown under the conditions of 25+ -0.5deg.C, 20 μm vertical cell, INSTEC: ALCT-IR1 test;
VHR represents a voltage holding ratio (%), and the test conditions were 60±1 ℃, voltage ±5V, pulse width 10ms, and voltage holding time 1.667s. The test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
K 11 to give the splay elastic constant, K 33 K is the bending elastic constant 22 For the torsional spring constant, the test conditions were: 25+ -2deg.C, INSTEC, ALCT-IR1, 20 μm vertical box;
CR represents the contrast of the liquid crystal display device, the contrast is the bright state of the liquid crystal display divided by the dark state of the liquid crystal display, the test condition is 25+/-1 ℃, the test voltage is the normal drive voltage, the test frequency is 64Hz, and the test equipment is DMS505;
the preparation method of the liquid crystal composition comprises the following steps: and weighing all the liquid crystal monomers according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker with all the liquid crystal monomers on a magnetic stirring instrument, heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the codes of the liquid crystal ring structure, the end group and the connecting group are represented by the following table 2 and table 3.
Table 2 corresponding codes of the ring structure
/>
TABLE 3 correspondence code of end groups to linking groups
/>
Examples:
the code is CC-Cp-V1;
the code is PGP-Cpr1-2;
the code is CPY-2-O2;
the code is CCY-3-O2;
the code is CLY-3-O2;
the code is PY-2O-O2;
the code is CCEY-2-O2;
the code is CPP-3-2V1;
the code is COY-3-O2;
the code is CCOY-3-O2;
the code is Sb-CpO-O4;
the code is Sc-CpO-O4; />
The code is Sa-2O-O5;
the code is CPU-3-F;
the code is CCP-V-OT;
the code is CPUQU-3-F;
the code is APUQU-3-F;
the code is DPU-3-F.
Composition 1
TABLE 4 formulation of liquid crystal composition 1 and corresponding Properties
/>
Composition 2
TABLE 5 formulation of liquid crystal composition 2 and corresponding Properties
Composition 3
TABLE 6 formulation of liquid crystal composition 3 and corresponding Properties
Composition 4
TABLE 7 formulation of liquid crystal composition 4 and corresponding Properties
The compounds of Table 1 and the compounds D1 to D8 were added as UV stabilizers to the liquid crystal composition in amounts of mass percent, based on 100 mass percent of the liquid crystal composition.
Investigation of Low temperature solubility of liquid Crystal composition
The compounds 1-1-5-1 to 1-4-5-1 and the comparative compounds D1 to D8 in table 1 were weighed by 0.3%, 0.5% and 1% by mass respectively, and added to the above compositions 1 to 4, then a stainless steel beaker containing a liquid crystal monomer was placed on a magnetic stirring apparatus to heat and melt, after the liquid crystal monomer in the stainless steel beaker was melted, a magnetic rotor was added to the stainless steel beaker, the mixture was stirred uniformly, cooled to room temperature and filtered with a 0.45um PTFE filter head, and then the prepared liquid crystal composition was transferred to a penicillin bottle (bulk), each bottle of liquid crystal was placed in a constant temperature glove box at-10 ℃, -20 ℃, -30 ℃, the presence or absence of precipitation or smectic of the liquid crystal in the bulk bottle was observed daily, and the continuous observation was continued for 30 days (30D), the longer the composition kept the liquid crystal phase, which indicates that the low temperature solubility of the liquid crystal composition was better. The corresponding low temperature test numbers are shown in Table 8, and the obtained test data are shown in Table 9.
Table 8 liquid crystal low temperature experiment numbering
/>
TABLE 9 liquid Crystal Low temperature Experimental data
/>
/>
/>
/>
/>
/>
Reliability of liquid crystal composition
The reliability of the liquid crystal composition is carried out by ultraviolet and high temperature aging tests and VHR tests, and the smaller the VHR data change of the liquid crystal composition before and after the ultraviolet and high temperature tests is, the stronger the ultraviolet and high temperature resistance is. Therefore, the uv resistance and the high temperature resistance were judged by comparing the differences of VHR data before and after the test of each example and comparative example.
The liquid crystal of the example and the liquid crystal of the comparative example are respectively poured into a test piece for testing, VHR represents voltage retention (%), the testing condition is 60+/-1 ℃, the voltage is +/-5V, the pulse width is 10ms, and the voltage retention time is 1.667s; the test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
the VHR initial value is data obtained by testing a test piece of the poured liquid crystal without any treatment;
VHR ultraviolet is VHR value obtained by testing a sheet filled with liquid crystal after 5000mJ irradiation under normal temperature ultraviolet light;
VHR high temperature aging is the VHR value obtained by placing a sheet filled with liquid crystal in a high temperature oven at 100 ℃ for 1 hour and then testing. The reliability test data are shown in Table 10:
TABLE 10 liquid Crystal reliability test data
/>
/>
/>
Scattering coefficient of liquid crystal composition
S LC ＝{(n e +n o ) 2 *△n 2 }/K ave
Wherein S is LC Is the scattering coefficient of the liquid crystal layer, and characterizes the scattering intensity; the balance being parameters of the liquid crystal material. The scattering coefficient experimental data are shown in table 11:
TABLE 11 Scattering coefficient Experimental data
/>
From the background art and the calculation formula, the smaller the scattering coefficient of the liquid crystal composition is, the better the contrast of the liquid crystal composition is. And the contrast of the scattering coefficient (contrast) adopts a parallel contrast principle, different liquid crystal compositions are applied to different display modes and different technical fields, and the measured scattering coefficients are different. The composition 1 of the invention is FFS/IPS mode negative liquid crystal composition; composition 2 is an FFS/IPS mode positive liquid crystal composition; composition 3 is a PSVA mode negative liquid crystal composition; composition 4 is a positive and negative mixed liquid crystal composition. Thus, the experiment was performed by adding different types of compounds of formula I and D1 to D8 to compositions 1, 2, 3, and 4, respectively, and recording experimental data.
From the above experimental data, the liquid crystal compound of the invention has a larger elastic constant K, a smaller scattering coefficient, good low-temperature intersolubility and simultaneously can effectively improve UV reliability, and the dielectric property of the liquid crystal compound of the invention is close to neutral, so that the liquid crystal compound can be applied to liquid crystal compositions with positive polarity and liquid crystal compositions with negative polarity, and the response speed of the negative liquid crystal composition is not reduced after the conventional tetrabiphenyl and pentabiphenyl UV-resistant stabilizer is added into the negative liquid crystal composition. The liquid crystal composition containing the liquid crystal compound has larger elastic constant K, smaller scattering coefficient, good low-temperature intersolubility and good UV resistance, and the response speed of the composition is not reduced when the liquid crystal compound is applied to a liquid crystal composition with negative dielectric. Meanwhile, the liquid crystal display element or the liquid crystal display containing the liquid crystal compound and the liquid crystal composition has the advantages of high response speed, good reliability, wide working temperature range and high contrast ratio.
The above examples of the present invention are merely illustrative of the present invention and are not intended to limit the embodiments of the present invention, and other variations or modifications of the present invention can be made by those skilled in the art based on the above description, and it is not intended to be exhaustive of all the embodiments, and all the obvious variations or modifications of the present invention are within the scope of the present invention.
Claims (11)
1. A liquid crystal compound is characterized in that the structural formula of the liquid crystal compound is shown as the following formula I,
wherein,
L 1 represent F, cl or an alkyl group having 1 to 5 carbon atoms;
L 2 、L 3 、L 4 、L 5 、L 6 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
2. The liquid crystal compound according to claim 1, wherein the compound represented by formula I is selected from the group consisting of compounds represented by the following formulas I-1 to I-4,
wherein,
L 2 、L 3 、L 4 、L 5 、L 6 each independently represents H, F, cl, C1-5 alkyl, C1-C-5-chain alkoxy, alkenyl having 2 to 5 carbon atoms or alkenyloxy having 3 to 5 carbon atoms;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
3. The liquid crystal compound according to claim 1 or 2, wherein the compound represented by formula I is selected from the group consisting of compounds represented by the following formulas I-1-1 to I-4-5,
wherein,
L 2 、L 3 、L 4 、L 5 each independently represents H, F, cl, a C1-5 chain alkyl group, a C1-5 chain alkoxy group, a C2-5 alkenyl group or a C3-5 alkenyloxy group;
L 61 h, F, cl, C2-5 alkyl, C2-5 alkoxy, C2-5 alkenyl, or C3-5 alkenyloxy;
L 62 represent H, cl, C1-5 alkyl and C atomsAn alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms;
R 1 、R 2 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms; and R is 1 、R 2 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, optionally non-O-linked-CH 2 Optionally substituted by O, any one or more hydrogen atoms may optionally be substituted by fluorine atoms.
4. A liquid crystal compound according to claim 3, wherein the compound represented by formula I is selected from the group consisting of compounds represented by the following formulas I-1-1-1 to I-4-5-2,
5. a liquid crystal composition comprising one or more liquid crystal compounds according to any one of claims 1 to 4.
6. The liquid crystal composition according to claim 5, wherein the liquid crystal composition further comprises one or more compounds represented by formula II and one or more compounds represented by formula III,
wherein,
R 3 、R 4 、R 5 、R 6 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms;
each independently represents->Or->
7. The liquid crystal composition according to claim 6, wherein the liquid crystal composition further comprises one or more compounds of formula IV,
wherein,
R 7 、R 8 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms, one or both of whichMultiple unconnected-CH 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
Z 1 represents a single bond, -CH 2 O or-CH 2 CH 2 -；
Each independently represents-> Or->
m, n each independently represents 0, 1 or 2, and m, n do not simultaneously represent 2, when m or n represents 2, a plurality of Each may be the same or different.
8. The liquid crystal composition according to claim 7, further comprising one or more compounds of formula V,
wherein,
R 9 、R 10 each independently represents an alkanyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms, wherein one or more are not connectedOf (C) CH 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
x represents O, S or-CH 2 O-。
9. The liquid crystal composition according to claim 6 to 8, wherein the liquid crystal composition further comprises one or more compounds of formula VI,
wherein,
R 12 represents an alkanyl radical having 1 to 10 carbon atoms or an alkenyl radical having 2 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 May be substituted with cyclopentylene, cyclopropyl ene or cyclobutylene;
R 13 representation F, CF 3 Or OCF (optical clear) 3 ；
Each independently represents-> Or->
r represents 1, 2 or 3, and when r represents 2 or 3, a plurality ofMay be the same or different.
10. The liquid crystal composition according to claim 9, wherein the liquid crystal composition further comprises one or more compounds of formula VII,
wherein,
R 14 represents an alkanyl radical having 1 to 10 carbon atoms, in which one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclopropylene or cyclobutylene;
t represents 0 or 1;
s represents 1, 2 or 3;
representation-> When s represents 2 or 3, a plurality of +.>May be the same or different.
11. A liquid crystal display element or a liquid crystal display, characterized by comprising the liquid crystal compound according to any one of claims 1 to 4 or the liquid crystal composition according to any one of claims 5 to 10, which is an active matrix display element or a display.
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