CN112143508A - Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device - Google Patents
Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device Download PDFInfo
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- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Abstract
The present invention relates to a liquid crystal compound represented by the following formula I having negative dielectric anisotropy, a liquid crystal composition, and a liquid crystal display device. The liquid crystal compound of the present invention can obtain a liquid crystal composition having a reduced rotational viscosity/elastic constant while maintaining a suitable dielectric anisotropy, and thus can obtain a liquid crystal display device having an improved response speed.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal material with negative dielectric anisotropy.
Background
Liquid crystal display elements are widely used in various household appliances such as watches and electronic computers, measuring instruments, automobile panels, word processors, computer printers, televisions, and the like.
The spatial arrangement of the liquid crystal molecules results in many of their properties being direction dependent. The dielectric constant of the liquid crystal molecules is different between the direction perpendicular to the two plates of the capacitor and the direction parallel to the two plates, when the dielectric constant is⊥(the longitudinal axis of the molecule is oriented perpendicular to the capacitor plates) is greater than the dielectric constant//(the alignment of the longitudinal axis of the molecules is parallel to the capacitor plates), the liquid crystal molecules are referred to as positive type liquid crystal compounds. When dielectric constant⊥Is less than//When used, the liquid crystal molecules are called negative type liquid crystal compounds.
With the continuous development of TFT-LCD, the wide viewing angle mode has become the target of pursuit in the industry, and the main current wide viewing angle technology mainly adopts VA vertical alignment, IPS in-plane switch, FFS fringe field switch, and other display types, which all require the liquid crystal medium to have higher light transmittance and smaller color shift. In particular, in IPS in-plane switching and FFS fringe field switching types, since an in-plane electric field is generated between electrodes when a voltage is applied, light penetration in the region is restricted, which increases power consumption and affects display effects, while negative type liquid crystal compounds are excellent in color shift and in the influence of a vertical electric field, and exhibit higher light penetration than positive type liquid crystal compounds, and thus are widely used.
However, the viscosity of the negative liquid crystal compounds currently available in the market is generally high, which is not favorable for improving the response speed. The response speed of the liquid crystal material is limited by the rotational viscosity/elastic constant K of the liquid crystal, so that the rotational viscosity of the liquid crystal medium needs to be reduced as much as possible, and the elastic constant K is increased to reduce the response time of the liquid crystal material, thereby realizing faster response. Practical studies show that the rotational viscosity of the liquid crystal material is closely related to the elastic constant, and the elastic constant is reduced while the rotational viscosity is reduced, so that the purpose of reducing the response time is difficult to achieve. Therefore, the development of a new method for obtaining a faster response speed based on a good rotational viscosity is a problem to be solved in the art.
Disclosure of Invention
The present inventors have intensively studied the problems of the prior art and found that a liquid crystal composition having a good rotational viscosity and a faster response speed can be provided by using the liquid crystal compound of the present invention represented by the following formula I having a negative dielectric anisotropy in a liquid crystal composition. Such liquid crystal compositions can be suitable in particular for monitor and TV applications based on the ECB effect or the IPS or FFS effect.
One aspect of the present invention provides a liquid crystal compound having negative dielectric anisotropy, which is a liquid crystal compound represented by formula I below:
in the formula I, A1、A2、A3Each independently represents a single bond, an alkylene group having 1 to 5 carbon atoms, an alkyleneoxy group having 1 to 5 carbon atoms, -O-, -CF2O-、-OCF2-、-C≡C-、-COO-、-OOC-、
R1、R6' independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, H, -CF3-CN, -F, oror-OCF3；
R2、R3、R4、R5Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5At least one of which is not H;
wherein the methylene group is optionally substituted with-O-, -S-, -COO-, -OOC-, or-CH ═ CH-;
m, n, p, q, h each independently represent 0, 1,2 or 3;
when q + h is not less than 2, a plurality of R2Optionally, the same or different, a plurality of R3Optionally, the same or different, a plurality of R4Optionally, the same or different, a plurality of R5Optionally the same or different.
In another aspect, the present invention further provides a liquid crystal composition comprising the aforementioned liquid crystal compound of formula I having negative dielectric anisotropy according to the present invention.
Although the liquid crystal composition of the present invention contains the liquid crystal compound represented by formula I having negative dielectric anisotropy of the present invention, the dielectric anisotropy of the liquid crystal composition of the present invention may be positive or negative.
In still another aspect of the present invention, it relates to a liquid crystal display device comprising the liquid crystal compound of the present invention, or comprising the liquid crystal composition of the present invention; the liquid crystal display device is an active matrix display device or a passive matrix display device.
Effects of the invention
By using the liquid crystal compound represented by formula I having negative dielectric anisotropy of the present invention, a liquid crystal composition having reduced rotational viscosity, rotational viscosity/elastic constant while maintaining appropriate dielectric anisotropy can be obtained, as compared with the prior art. The liquid crystal composition of the present invention contains the liquid crystal compound of the present invention, and thus has reduced rotational viscosity and rotational viscosity/elastic constant while maintaining appropriate dielectric anisotropy, and can be used for developing a liquid crystal display device having fast response characteristics.
In particular, they have a short response time when used for monitor, television display, and in particular exhibit no image sticking or exhibit significantly reduced image sticking after a long period of operation.
Especially in the case of VA, IPS, FFS displays, and in PM (passive matrix) -VA displays, the rotational viscosity can be reduced and the response improved.
Drawings
FIG. 1 shows a mass spectrum of the compound (C4) PY-3-O2 (formula II-11) prepared in Synthesis example 1 of the present invention.
Detailed Description
[ liquid Crystal Compound ]
The liquid crystal compound of the invention is a liquid crystal compound with negative dielectric anisotropy and shown in the following formula I:
in the formula I, A1、A2、A3Each independently represents a single bond, an alkylene group having 1 to 5 carbon atoms, an alkyleneoxy group having 1 to 5 carbon atoms, -O-, -CF2O-、-OCF2-、-C≡C-、-COO-、-OOC-、
Examples of the "alkylene group having 1 to 5 carbon atoms" include methylene, ethylene, 1, 3-propylene, 1, 2-propylene, 1, 4-butylene, isobutylene and pentylene.
Examples of the "alkyleneoxy group having 1 to 5 carbon atoms" include methyleneoxy group, ethyleneoxy group, 1, 3-propyleneoxy group, 1, 2-propyleneoxy group, 1, 4-butyleneoxy group, isobutyleneoxy group, pentyleneoxy group, and the like.
The foregoing "any H atom is optionally substituted by F or CH3By-substituted is meant that A1、A2、A3Any H atom in the groups represented by (a) may be substituted with a fluorine atom or a methyl group, and the number of the substituted H atoms is not particularly limited.
A1、A2、A3Each independently preferably a single bond, methylene, ethylene, methyleneoxy, ethyleneoxy, or mixtures thereof,
And A is1、A2、A3At least one of which is
R1、R6' independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or a CCycloalkyl having 3 to 6 atoms, H, -CF3-CN, -F, or, -OCF3；
Examples of the "alkyl group having 1 to 7 carbon atoms" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, hexyl, and heptyl.
Examples of the "alkoxy group having 1 to 7 carbon atoms" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, hexoxy, and heptoxy.
Examples of the "alkenyl group having 2 to 7 carbon atoms" include vinyl, propenyl, isopropenyl, n-butenyl, isobutenyl, pentenyl, hexenyl, heptenyl and the like.
Examples of the "cycloalkyl group having 3 to 6 carbon atoms" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopropyl and methylcyclobutyl.
R1、R6' independently of one another, methyl, ethyl, n-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclopentyl, methoxy, ethoxy, n-propoxy, n-pentoxy, ethenyl, propenyl, isopropenyl, n-butenyl, isobutenyl, pentenyl are preferred.
R2、R3、R4、R5Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
Examples of the "alkyl group having 1 to 5 carbon atoms" include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, and isopentyl group.
Examples of the "alkoxy group having 1 to 5 carbon atoms" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, and isopentoxy.
Examples of the "alkenyl group having 2 to 4 carbon atoms" include an ethenyl group, a propenyl group, an isopropenyl group, a n-butenyl group, and an isobutenyl group.
R2、R3、R4、R5At least one of which is not H;
wherein the methylene group is optionally substituted by-O-, -S-, -COO-, -OOC-, or-CH ═ CH-;
m, n, p, q, h each independently represent 0, 1,2 or 3;
when q + h is not less than 2, a plurality of R2Optionally, the same or different, a plurality of R3Optionally, the same or different, a plurality of R4Optionally, the same or different, a plurality of R5Optionally the same or different.
The liquid crystal compound of the present invention is preferably selected from the group consisting of compounds represented by the following structural formulae I-1 to I-27.
Wherein R is1、R6' independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5At least one of which is not H.
In the liquid crystal compound of the present invention, it is further preferably selected from the group consisting of compounds represented by the following structural formulae II-1 to II-24.
[ preparation of liquid Crystal Compound ]
The method for producing the liquid crystal compound represented by formula I having negative dielectric anisotropy of the present invention is not particularly limited, and those skilled in the art can select appropriate raw materials and reaction routes according to the prior art to produce the liquid crystal compound. For example, the preparation can be carried out with reference to synthetic examples described later.
[ liquid Crystal composition ]
The liquid crystal composition comprises the compound shown in the formula I and having negative dielectric anisotropy.
In the liquid crystal composition of the present invention, the content of the liquid crystal compound represented by the formula I is not particularly limited. In view of obtaining suitable Δ n, Δ, ratio of rotational viscosity/elastic constant, etc., the liquid crystal composition of the present invention preferably contains the liquid crystal compound represented by formula I in an amount of 1 to 60 wt%, preferably 1 to 50 wt%, and more preferably 10 to 40 wt%.
The liquid crystal composition provided by the invention optionally further comprises a compound shown in the following formula IV:
in the formula IV, R6、R7Each independently represents any one of the following groups (i) to (v):
linear alkyl with 1-7 carbon atoms or linear alkoxy with 1-7 carbon atoms;
(ii) one or more-CH groups in any of the groups shown in (i)2-a group formed by substitution with-O-, -COO-, -OOC-, or-CH ═ CH-;
(iii) one or more-H in any of the groups represented by (i) is-F, -Cl, -CH2or-CH ═ CH-CH3Substitution of the formed group;
fourthly, naphthenic base with 3 to 6 carbon atoms;
⑤H、-CF3-CN, -F, or, -OCF3；
Examples of the "straight-chain alkyl group having 1 to 7 carbon atoms" include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, and an n-heptyl group.
Examples of the "linear alkoxy group having 1 to 7 carbon atoms" include a methoxy group, an ethoxy group, an n-propyloxy group, an n-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, and an n-heptyloxy group.
m ', n ', o ' each independently represent 0 or 1;
Z1’、Z2’、Z3' each independently represents a single bond, -C2H4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CH2O-、-OCH2-、-CF2O-, or, -OCF2-, wherein any H is optionally replaced by F.
Preferably, the aforementioned compound represented by formula IV is selected from the group consisting of the following compounds.
Wherein the content of the first and second substances,
each independently selected from the group consisting of the following groups.
In the liquid crystal composition of the present invention, the content of the compound represented by formula IV is not particularly limited. The content of the compound represented by formula IV may be, for example, 0 to 50% by weight. From the viewpoint of obtaining a suitable dielectric constant, the range of 20 to 45% is preferable.
The liquid crystal composition of the present invention may optionally further comprise a compound represented by the following formula V:
in the formula V, R8、R9Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or H; r8、R9In any of-CH2-is optionally substituted by-CH2O-、-OCH2-or-C ═ C-is substituted, any H is optionally substituted by F;
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, and decyl groups.
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.
Examples of the "cycloalkyl group having 3 to 6 carbon atoms" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopropyl and methylcyclobutyl.
p ', q ', r ' each independently represent 0 or 1;
Z4’、Z5’、Z6' each independently represents a single bond, -C2H4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CH2O-、-OCH2-、-CF2O-or-OCF2-, wherein any H is optionally replaced by F.
Further, the compound represented by the formula V is preferably selected from the group consisting of the following compounds.
Wherein, (F) represents F or H.
In the liquid crystal composition of the present invention, the compound represented by the formula V is an optional component, and the content thereof may be, for example, 0 to 70% by weight. In view of low-temperature solubility and reliability, the content is preferably in the range of 10 to 60%.
In addition to the liquid crystal compounds listed above, those skilled in the art can add other liquid crystal compounds to the liquid crystal composition of the present invention without impairing the desired properties of the liquid crystal composition.
The liquid crystal composition of the present invention may optionally contain various functional dopants, and examples of the functional dopants include antioxidants, ultraviolet absorbers, and chiral agents.
As described above, although the liquid crystal composition of the present invention contains the liquid crystal compound represented by formula I having negative dielectric anisotropy of the present invention, the composition of the present invention is not necessarily negative dielectric anisotropy, and may be positive dielectric anisotropy. The composition and ratio of the components of the composition can be adjusted as desired by those skilled in the art to obtain a composition having the desired anisotropy.
[ liquid Crystal display device ]
The third aspect of the present invention provides a liquid crystal display device, which is not particularly limited as long as it contains any of the liquid crystal compositions described above. The liquid crystal display device of the present invention may be an active matrix display device or a passive matrix display device. Those skilled in the art can select a suitable liquid crystal display element or liquid crystal display structure according to the desired performance.
Examples
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method unless otherwise specified, the used raw materials can be obtained from a public commercial way unless otherwise specified, the percentages refer to mass percentage, the temperature is centigrade (DEG C), and the liquid crystal compound is also a liquid crystal monomer.
Synthesis example 1
A compound represented by the formula II-11 was prepared in the following synthetic steps 1 to 6.
Synthesis step 1
100ml of tetrahydrofuran and lithium aluminium hydride (8g, 0.21mol) were added to a three-necked flask under nitrogen. The temperature was reduced to below 0 ℃ and a solution of A-1(28.4g, 0.2mol) dissolved in 100ml of tetrahydrofuran was added dropwise. After the addition, the temperature was gradually raised to room temperature, and the reaction was carried out overnight. GC confirmed that the starting material remained, and the reaction mixture was cooled to 0 ℃ or lower, and then poured into ice water. And (4) filtering the hydrolysate with diatomite to obtain a clear solution. Then, the mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. 28.3g of the crude product A-2 thus obtained were used as they were in the next step.
Synthesis step 2
200ml of methylene chloride and crude A-2(28g, 0.19mol) from example 1, step 1 were added to a three-necked flask. The temperature was reduced to 5-10 ℃ and phosphine tribromide (54g, 0.2mol) was added dropwise to dissolve in 150ml of dichloromethane solution. After the addition was complete, the mixture was allowed to slowly warm to room temperature and was kept at room temperature for overnight stirring. After the reaction solution was quenched by pouring crushed ice, the reaction solution was extracted twice with dichloromethane, the organic phases were combined, washed three times with 200ml of tap water, and dried over anhydrous sodium sulfate. After vacuum desolventizing, the mixture was passed through a silica gel column to obtain 44.5g of pale yellow liquid A-3.
Synthesis step 3
Para-bromophenylacetonitrile (57g, 0.15mol) is added into a three-neck flask, 280ml of DMF is added subsequently, the temperature is reduced to minus 10 ℃, sodium hydride (7.6g, 0.32mol,60 percent of sodium hydride is dispersed in mineral oil) is slowly added, and the temperature is kept between minus 5 ℃ and 5 ℃ for 30 minutes after the addition. Then, the temperature is reduced to-10 ℃ to-15 ℃, and a solution of the pale yellow liquid A-3(40.8g, 0.15mol) obtained in the synthesis step 2 in 150ml of DMF is added dropwise. After the addition was complete, the mixture was allowed to slowly warm to room temperature and was kept at room temperature for overnight stirring. After the reaction solution was quenched by pouring crushed ice, the mixture was extracted twice with dichloromethane, the organic phases were combined, washed with saturated brine to neutrality, and dried over anhydrous sodium sulfate. After vacuum desolventization, the mixture was passed through a silica gel column to obtain 43.8g of pale yellow solid A-4.
Synthesis step 4
Under nitrogen protection, the pale yellow solid A-4(36.8g, 0.12mol) obtained in the aforementioned Synthesis step 3 was added to a three-necked flask, followed by addition of 150ml of anhydrous toluene and stirring to dissolve completely. The temperature is reduced to 0 ℃, and diisobutylaluminum hydride (1.5mol x L) is slowly added dropwise-1Toluene solution) 100ml, and after the addition is finished, the temperature is kept between 0 ℃ and 10 ℃ for 30 minutes. Then, the temperature was naturally raised to room temperature, and the reaction was stirred overnight. After the reaction is finished, pouring crushed ice into the reaction liquid for quenching, extracting twice by using toluene, combining organic phases, washing the organic phases to be neutral by using saturated saline, and drying the organic phases by using anhydrous sodium sulfate. After vacuum desolventization, the mixture was passed through a silica gel column to give 32.4g of a yellow oil, which was recrystallized from n-heptane to give 25.6g of a pale yellow solid A-5.
Synthesis step 5
Under nitrogen protection, the pale yellow solid A-5(25.0g, 0.08mol) obtained in the aforementioned Synthesis step 4 was added to a three-necked flask, followed by addition of 150ml of trifluoroacetic acid and stirring to dissolve completely. The temperature was reduced to 0 ℃ and triethylsilane (23.2g, 0.2mol) was added dropwise. Then naturally raising the temperature to room temperature, and stirring the reaction until no raw material aldehyde remains. The reaction solution was vacuum-dried, quenched with water, extracted twice with ethyl acetate, the organic phases were combined, washed with saturated brine to neutrality, and dried over anhydrous sodium sulfate. After vacuum desolventizing, the mixture was passed through a silica gel column to obtain 22.4g of pale yellow solid A-6, which was directly subjected to the next reaction.
Synthesis step 6
After nitrogen substitution, A-6(20.6g, 0.07mol), 100ml of toluene, and 40ml of ethanol were sequentially added to a three-necked flask, and stirring was started, followed by addition of potassium carbonate (19.4g, 0.14mol), and 20ml of deionized water. The temperature was raised to 40 ℃ and Compound A-7(15.6g, 0.077mol), hydrazine hydrate 1ml and tetrakistriphenylphosphine palladium 0.5g were added. The reaction was refluxed for 6 hours at elevated temperature. 100ml of water was added, extraction was performed twice with ethyl acetate, and the organic phases were combined, washed with saturated brine to neutrality, and dried over anhydrous sodium sulfate. Vacuum desolventizing, passing through silica gel column, crystallizing to obtain 20g (II-11) of white powder, and detecting by gas chromatography, wherein the purity is 99.9%.
[ liquid Crystal composition ]
Liquid crystal compositions of different compositions were prepared in examples a and B, examples 1 to 7 and comparative examples 1 and 2, wherein the monomer structures, the amounts (weight percentages) of the specific compounds used in the respective examples, and the results of the performance parameter tests of the resulting liquid crystal media are shown in the following tables A, B and 1 to 9, respectively.
The temperature units involved in the examples are, and the specific meanings of the other symbols and the test conditions are as follows:
gamma1(mpa.s) represents the rotational viscosity coefficient of the liquid crystal compound, and the measurement method: the equipment INSTEC comprises ALCT-IR1, a vertical box with the thickness of 18 microns in a test box, the temperature of 25 ℃, and the short term G1;
K11is a torsional elastic constant, K33For the splay spring constant, the test conditions were: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
G1/K11indicating the response time of the horizontal alignment mode, the lower the value of G1/K11, the faster the response speed in the horizontal alignment;
G1/K33 denotes the response time of the vertical alignment mode, G1/K33A lower value of (d) indicates a faster response speed in the vertical alignment;
Δ represents dielectric anisotropy, Δ ═//-⊥Wherein, in the step (A),//is the dielectric constant parallel to the molecular axis,⊥for the dielectric constant perpendicular to the molecular axis, test conditions: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neFor the refractive index of extraordinary rays, test conditions: 589nm, 25 + -0.2 deg.C.
In the present invention, the liquid crystal composition is prepared as follows: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for 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 obtained liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test.
The structures of the liquid crystal monomers used in the examples of the present invention are represented by the following codes, and the methods for representing the codes of the liquid crystal ring structures, the terminal groups, and the linking groups are shown in the following tables (i) and (ii).
Table (one): corresponding code of ring structure
Table (ii): corresponding codes for end groups and linking groups
Examples are:
the liquid crystal compositions of examples A and 1 to 7, which exhibited negative dielectric anisotropy, and the liquid crystal composition of example B, which exhibited positive dielectric anisotropy, were obtained by using the novel liquid crystal compound synthesized as described above and blending with other components. The compositions and contents of the components of the liquid crystal compositions of example A, B and examples 1 to 7 are shown in the following tables A, B and tables 1 to 7.
Table a component ratios and performance parameters for the liquid crystal composition of example a
Table B component ratios and performance parameters of the liquid-crystalline media of example B
TABLE 1 component ratios and performance parameters of the liquid-crystalline media of example 1
TABLE 2 component ratios and performance parameters of the liquid-crystalline media of example 2
Table 3 component ratios and performance parameters of the liquid-crystalline medium of example 3
Table 4 component ratios and performance parameters of the liquid-crystalline medium of example 4
TABLE 5 component ratios and Property parameters of the liquid-crystalline media of example 5
TABLE 6 component ratios and Performance parameters of the liquid-crystalline medium of example 6
TABLE 7 component ratios and performance parameters of the liquid-crystalline media of example 7
The formulations of comparative examples 1 and 2 are shown in tables 8 to 9 below, and the components thereof do not contain the novel liquid crystal compound of the present invention, that is, the liquid crystal compound represented by the formula I described above.
TABLE 8 component ratios and performance parameters of the liquid-crystalline media of comparative example 1
TABLE 9 component ratios and performance parameters of the liquid-crystalline media of comparative example 2
The compound of formula I in example 1 was replaced with the general-purpose negative-type liquid crystal compound in the foregoing comparative example 1, and the compound of formula I in example 7 was replaced with the general-purpose negative-type liquid crystal compound in comparative example 2.
It can be found from the comparison between the examples and the comparative examples that the liquid crystal composition of the examples containing the compound of formula I can obtain reduced viscosity and ratio of viscosity/elastic coefficient while maintaining suitable optical anisotropy value and dielectric anisotropy property, and can reduce response time of horizontal alignment and vertical alignment modes, thereby improving response speed and realizing fast response, compared with the comparative examples 1 and 2 not containing the compound of formula I.
Although the present invention is not exhaustive of all liquid crystal mixtures claimed, it is anticipated by those skilled in the art that other liquid crystal materials of the same type can be obtained in a similar manner without creative efforts based on the disclosed embodiments, only by combining with their own professional efforts. And are merely representative of embodiments, given the limited space available.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A liquid crystal compound having negative dielectric anisotropy represented by the following formula I:
in the formula I, A1、A2、A3Each independently represents a single bond, an alkylene group having 1 to 5 carbon atoms, an alkyleneoxy group having 1 to 5 carbon atoms, -O-, -CF2O-、-OCF2-、
-COO-、-OOC-、
Or,
Wherein any H atom is optionally substitutedF or CH3-substitution; and A is1、A2、A3At least one of which is
R1、R6' independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5At least one of which is not H;
m, n, p, q, h each independently represent 0, 1,2 or 3;
when q + h is not less than 2, a plurality of R2Optionally, the same or different, a plurality of R3Optionally, the same or different, a plurality of R4Optionally, the same or different, a plurality of R5Optionally the same or different.
2. The liquid crystal compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the following formulae I-1 to I-27:
wherein R is1、R6' independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, H, -CF3-CN, -F, or, -OCF3；
R2、R3、R4、R5At least one of which is not H.
3. The liquid crystal compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the following formulae II-1 to II-24:
4. a liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 3.
5. The liquid crystal composition of claim 4, further comprising a compound of formula IV:
in the formula IV, R6、R7Each independently represents any one of the following groups (i) to (v):
linear alkyl with 1-7 carbon atoms or linear alkoxy with 1-7 carbon atoms;
(ii) one or more-CH groups in any of the groups shown in (i)2-a group formed by substitution with-O-, -COO-, -OOC-, or-CH ═ CH-;
(iii) one or more-H in any of the groups represented by (i) is-F, -Cl, -CH2or-CH ═ CH-CH3Substitution of the formed group;
fourthly, naphthenic base with 3 to 6 carbon atoms;
⑤H、-CF3-CN, -F or-OCF3；
m ', n ', o ' each independently represent 0 or 1;
Z1’、Z2’、Z3' each independently represents a single bond, -C2H4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CH2O-、-OCH2-、-CF2O-, or, -OCF2-, wherein any H is optionally replaced by F.
6. The liquid crystal composition of claim 5, wherein the compound of formula IV is selected from the group consisting of:
wherein the content of the first and second substances,
each independently selected from the group consisting of:
7. the liquid crystal composition according to any one of claims 4 to 6, further comprising a compound represented by the following formula V:
in the formula V, R8、R9Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or H; r8、R9In any of-CH2-is optionally substituted by-CH2O-、-OCH2-or-C ═ C-is substituted, any H is optionally substituted by F;
p ', q ', r ' each independently represent 0 or 1;
Z4’、Z5’、Z6' each independently represents a single bond, -C2H4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CH2O-、-OCH2-、-CF2O-or-OCF2-, wherein any H is optionally replaced by F.
8. The liquid crystal composition of claim 7, wherein the compound of formula V is selected from the group consisting of:
wherein, (F) represents F or H.
9. The liquid crystal composition according to claim 8, wherein the liquid crystal compound represented by formula I is 1 to 60 wt%, the compound represented by formula IV is 0 to 50 wt%, and the compound represented by formula V is 1 to 70 wt%.
10. A liquid crystal display device comprising the liquid crystal compound according to any one of claims 1 to 3, or comprising the liquid crystal composition according to any one of claims 4 to 9; the liquid crystal display device is an active matrix display device or a passive matrix display device.
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| CN113403088A (en) * | 2021-06-17 | 2021-09-17 | 烟台显华化工科技有限公司 | Negative dielectric anisotropy liquid crystal composition and liquid crystal display device |
| CN114149812A (en) * | 2021-12-27 | 2022-03-08 | 苏州汉朗光电有限公司 | Negative liquid crystal composition and application thereof |
| CN114231295A (en) * | 2021-12-27 | 2022-03-25 | 苏州汉朗光电有限公司 | Liquid crystal composition containing substituted cyclohexyl compound and application thereof |
| CN114231293A (en) * | 2021-12-27 | 2022-03-25 | 苏州汉朗光电有限公司 | Negative dielectric liquid crystal composition and application thereof |
| CN114231296A (en) * | 2021-12-27 | 2022-03-25 | 苏州汉朗光电有限公司 | Negative liquid crystal composition and application |
| CN114231294A (en) * | 2021-12-27 | 2022-03-25 | 苏州汉朗光电有限公司 | Negative liquid crystal composition and application thereof |
| CN114350380A (en) * | 2022-01-13 | 2022-04-15 | 烟台显华科技集团股份有限公司 | Negative dielectric anisotropy liquid crystal composition, optical anisotropic medium and liquid crystal display device |
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| CN112143508B (en) | 2022-03-18 |
| WO2022073400A1 (en) | 2022-04-14 |
| TW202214827A (en) | 2022-04-16 |
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