CN113956888B - Negative liquid crystal composition and application thereof - Google Patents
Negative liquid crystal composition and application thereof Download PDFInfo
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- CN113956888B CN113956888B CN202111365467.2A CN202111365467A CN113956888B CN 113956888 B CN113956888 B CN 113956888B CN 202111365467 A CN202111365467 A CN 202111365467A CN 113956888 B CN113956888 B CN 113956888B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 263
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims description 159
- 230000004044 response Effects 0.000 abstract description 25
- 230000003287 optical effect Effects 0.000 abstract description 14
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 49
- 125000004432 carbon atom Chemical group C* 0.000 description 41
- 125000003342 alkenyl group Chemical group 0.000 description 34
- 125000003545 alkoxy group Chemical group 0.000 description 32
- 239000000463 material Substances 0.000 description 32
- 125000005819 alkenylalkoxy group Chemical group 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 21
- 238000005259 measurement Methods 0.000 description 14
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 13
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- -1 terphenyl compound Chemical class 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000012769 display material Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QZGUYBAIILRCEG-UHFFFAOYSA-N 1,2-difluorodibenzofuran Chemical compound C1=CC=C2C3=C(F)C(F)=CC=C3OC2=C1 QZGUYBAIILRCEG-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Abstract
The invention provides a negative crystal composition and application thereof, wherein the liquid crystal composition is particularly favorable for adjusting the optical anisotropy value of a system, improving the temperature range of liquid crystal display and particularly favorable for manufacturing a liquid crystal display device with quick response.
Description
The present invention is a division of the prior invention patent with the application number 201910504856.5 and the application date is 2019.06.12. This division is written based on examples 3 and 4 of the parent specification.
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and application thereof.
Background
In the 60 s of the 20 th century, RCA corporation discovered for the first time that the light transmission mode of liquid crystals was changed by electric stimulation, and then after the liquid crystal display technology was released by applying this property, liquid crystals gradually attracted high attention and rapidly developed to various fields. In 1966, duPont had synthesized Kevlar fibers using aramid liquid crystals, and the liquid crystal materials began the industrialization process. Through rapid development for decades, the liquid crystal material has been widely applied to various fields such as display technology, optical storage equipment, solar cells and the like by virtue of the special properties, and the research scope is more over the fields such as chemistry, biology, information science and the like, so that the liquid crystal material becomes one of the favored and indispensable novel materials in the current society.
Liquid crystal displays can be divided into passive matrix (also called passive matrix or simple matrix) and active matrix (also called active matrix) driving methods. Among them, the active matrix lcd is to change the arrangement of liquid crystal compounds by applying a voltage, so as to change the light emission intensity of the backlight source to form an image, and is increasingly popular due to its characteristics of high resolution, high contrast, low power, thin surface and light weight. Active matrix liquid crystal displays can be classified into two types according to active devices: a MOS (metal oxide semiconductor) or other diode on a silicon chip as a substrate; among them, the most rapidly developed thin film transistor (Thin Film Transistor-TFT) is a thin film transistor liquid crystal display (TFT-LCD) which has been well applied to display devices such as mobile phones, computers, liquid crystal televisions, cameras, etc., and is the mainstream product of the liquid crystal market.
With the continuous development of TFT-LCDs, a wide viewing angle mode has become a target pursued in the industry, and currently, the main wide viewing angle technologies mainly include VA vertical alignment technology, IPS in-plane switching technology, FFS fringe field switching technology, and the like, which all require higher light transmittance and smaller color shift. For the IPS in-plane switching technology and FFS fringe field switching technology, since an in-plane electric field is generated between electrodes when a voltage is applied, light transmission in the region is limited, which increases power consumption and affects display effects, while the negative type liquid crystal compound exhibits superior color shift and is affected by a vertical electric field, and exhibits higher light transmittance than the positive type material, and thus is widely used. However, the viscosity of the general negative liquid crystal material in the market is generally higher, which is unfavorable for the improvement of response speed, so the development of the liquid crystal material with low viscosity and high negative dielectric constant becomes the main research direction of the current negative liquid crystal material.
With the wide application of liquid crystal displays, the requirements on the performance of the liquid crystal displays are continuously improved, and the wider working temperature, the faster response speed and the higher contrast ratio are required, so that the improvement of the performance is not separated from the improvement of the liquid crystal material.
Disclosure of Invention
The invention aims to provide a liquid crystal composition with negative dielectric constant, which is beneficial to adjusting the optical anisotropy value of a system, improving the temperature range of liquid crystal display, and further improving the response speed and the service temperature range of liquid crystal display.
It is another object of the present invention to provide the use of the above liquid crystal composition.
The technical scheme is as follows: in order to achieve the above object, according to one aspect of the present invention, there is provided a liquid crystal composition comprising at least one liquid crystal compound having the general formula I, at least one liquid crystal compound having the general formula II and at least one liquid crystal compound having the general formula III,
The general formula I is:
Wherein,
R and R' are each independently selected from H, F, C to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenylalkoxy, wherein H may be substituted with cyclopentyl or F, CH 2 may be substituted with cyclopentyl, O, or F, and two adjacent CH 2 may not be simultaneously substituted with O; or R and R' are each independently selected from cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, or C2-C7 alkenylalkoxy substituted cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl; or R and R' are each independently selected from cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl;
a is selected from 0, 1 or 2;
Selected from the group consisting of Any one of the group consisting of;
when a is a number of times 1, the number of times, Selected from the group consisting of Any one of the group consisting of;
When a is 2, two are included in the formula I.e.Appear twice in the general formula, at each occurrenceEach independently selected from Any one of the group consisting of;
The general formula II is:
II1、 and/or
II2、And/or
II3、
Wherein R 1 and R 1' are each independently selected from C1-C7 alkyl or C2-C7 alkenyl, wherein H may be substituted with cyclopentyl or F, CH 2 may be substituted with cyclopentyl, O or F, and two adjacent CH 2 may not be simultaneously substituted with O;
The general formula III is:
Wherein R 2 and R 2' are each independently selected from the group consisting of H, C C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, and C2 to C7 alkenylalkoxy, wherein H or CH 2 may be substituted with cyclopentyl or F; or R 2 and R 2' are each independently selected from cyclopentyl, or are C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentyl;
Each independently selected from
Any one of the group consisting of.
According to another aspect of the present invention, there is provided the use of the above liquid crystal composition in a liquid crystal display material or a liquid crystal display device.
The beneficial effects are that: the liquid crystal composition is beneficial to adjusting the optical anisotropy value of a system, improving the temperature range of liquid crystal display, and further improving the response speed and the service temperature range of liquid crystal display.
Detailed Description
It should be noted that, without conflict, the embodiments of the present application and features of the embodiments may be combined with each other. The present application will be described in detail with reference to examples.
In one exemplary embodiment of the present invention, a liquid crystal composition is provided that includes at least one liquid crystal compound having the formula I, at least one liquid crystal compound having the formula II, and at least one liquid crystal compound having the formula III.
The general formula I is:
Wherein,
R and R' are each independently selected from H, F, C to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenylalkoxy, wherein H may be substituted with cyclopentyl or F, CH 2 may be substituted with cyclopentyl, O, or F, and two adjacent CH 2 may not be simultaneously substituted with O; or R and R' are each independently selected from cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, or C2-C7 alkenylalkoxy substituted cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl; or R and R' are each independently selected from cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl;
a is selected from 0, 1 or 2;
Selected from the group consisting of
Any one of the group consisting of;
when a is a number of times 1, the number of times, Selected from the group consisting of
Any one of the group consisting of;
When a is 2, two are included in the formula I.e.Appear twice in the general formula, at each occurrenceEach independently selected from Any one of the group consisting of;
The general formula II is:
II1、 and/or
II2、And/or
II3、
Wherein R 1 and R 1' are each independently selected from C1-C7 alkyl or C2-C7 alkenyl, wherein H may be substituted with cyclopentyl or F, CH 2 may be substituted with cyclopentyl, O or F, and two adjacent CH 2 may not be simultaneously substituted with O;
The general formula III is:
Wherein R 2 and R 2' are each independently selected from the group consisting of H, C C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, and C2 to C7 alkenylalkoxy, wherein H or CH 2 may be substituted with cyclopentyl or F; or R 2 and R 2' are each independently selected from cyclopentyl, or are C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentyl;
Each independently selected from Any one of the group consisting of.
The liquid crystal compound having the general formula I is white in a pure state and is a liquid crystal compound having negative dielectric anisotropy, and the liquid crystal compound having negative dielectric constant is characterized by having a large dipole effect in a direction perpendicular to a long axis of a molecule, and thus a relatively large component of the corresponding dielectric constant in a vertical direction, that is, a high vertical dielectric constant epsilon ⊥, and thus the dielectric anisotropy Δepsilon=epsilon //-ε⊥ exhibits a negative value. The liquid crystal molecules tend to be distributed along the direction perpendicular to the electric field due to the higher vertical dielectric constant epsilon ⊥, and the negative liquid crystal material is arranged on the horizontal plane under the fringe electric field, and the pretilt angle distribution is more uniform than that of the positive material, so that the liquid crystal material has higher light transmittance and wide viewing angle, and is particularly suitable for preparing VA, PSVA, IPS and FFS type liquid crystal materials with high transmittance and wide viewing angle; in addition, the addition of the liquid crystal compound with negative dielectric constant can improve the bending elastic coefficient K 33 of the system, so that the light transmittance and contrast ratio of the whole system can be improved, the energy conservation is facilitated, the image display quality can be improved, and the performance requirement of liquid crystal display can be better met.
The liquid-crystalline compounds of the general formula II are white in the pure state and have a relatively high value of the optical anisotropy Δn and a relatively broad nematic temperature range. Generally, when light enters an anisotropic material, it is generally divided into two waves having vibration directions perpendicular to each other and different propagation speeds, and the two waves have two refractive rays, respectively, to form so-called birefringence, and the refractive index of the material for parallel light and for perpendicular light is obtained by using a polarizer, and the difference is taken as the optical anisotropy Δn. And the refractive index is closely related to the arrangement of charges, the more compact the arrangement of charges, the greater the refractive index. The compound of the general formula II is a conjugated terphenyl compound, the conjugated structure of the benzene ring can be hybridized with the lone pair electrons carried by the O atoms of the adjacent tail chains to form larger electron cloud overlap, and the conjugated structure is larger than that of a pure terphenyl compound, so that the conjugated structure has a larger refractive index, and the nematic phase temperature range of liquid crystal molecules is increased. In LCD display, the value of the optical path difference d·Δn is preset, the higher the Δn value is, the lower the d value is, and the response speed is inversely proportional to the d value, so that a high Δn is advantageous for manufacturing a fast-response liquid crystal display device.
The liquid crystal compound with the general formula III is white or transparent colloid in a pure substance state, is a liquid crystal compound with weak polarity or nonpolar, and is characterized by lower rotational viscosity and lower melting point, so that the liquid crystal compound with the general formula III has better intersolubility and improves the viscosity and low-temperature reliability of liquid crystal materials when being mixed with other liquid crystal compounds.
Therefore, the liquid crystal compound of the general formula I and the liquid crystal compound of the general formula II and the general formula III are combined together, so that the advantage of high negative dielectric constant of the negative liquid crystal material can be maintained, and the defects of the negative liquid crystal material in refractive index, viscosity and liquid crystal width can be improved, so that the liquid crystal material with lower driving voltage, wider working temperature and faster response speed can be obtained.
Furthermore, it should be clear to a person skilled in the art that the above alkyl groups include not only straight chain alkyl groups but also corresponding branched chain alkyl groups.
In order to obtain a more suitable liquid crystal width, a higher dielectric anisotropy value, a smaller rotational viscosity and a suitable elastic coefficient K, which are more advantageous for improving the response speed of the liquid crystal material, reducing the threshold voltage and improving the intersolubility of the liquid crystal material, in a preferred embodiment of the present application, the liquid crystal compound having a negative dielectric constant of the general formula I is a negative polarity liquid crystal compound having the formulas I1 to I34, and the liquid crystal compound having a low rotational viscosity of the general formula III is preferably a liquid crystal compound having the formulas III1 to III 3.
The above compounds of the general formulae I1 to I34 are of the formula:
Wherein Y and Y' are each independently selected from H, F, C to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenylalkoxy, wherein H may be substituted with cyclopentyl or F, CH 2 may be substituted with cyclopentyl, O, or F, and two adjacent CH 2 may not be simultaneously substituted with O; or Y and Y' are each independently selected from cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, or C2-C7 alkenylalkoxy substituted cyclopentyl, oxycyclopentyl, oxymethyl cyclopentyl, oxyethyl cyclopentyl; or the Y and Y' are each independently selected from cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl, or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentenyl, oxocyclopentenyl, oxymethylcyclopentenyl, oxoethylcyclopentenyl.
The above compounds having the general formulae III1 to III3 are as follows:
III1、
III2、
III3、
Wherein Y 2 and Y 2' are each independently selected from the group consisting of H, C C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, and C2-C7 alkenylalkoxy, wherein H or CH 2 may be substituted with cyclopentyl or F; or the Y 2 and Y 2' are each independently selected from cyclopentyl, or are C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentyl.
When the liquid crystal composition is combined with other liquid crystal compounds to form a liquid crystal mixture with a negative dielectric constant, the characteristics of the liquid crystal composition with the negative dielectric constant can be adjusted in a wider range, so that the performance requirements of more liquid crystal materials are met. The liquid crystal composition of the present invention has good compatibility with other liquid crystal compounds, and is less limited in the types of other liquid crystal compounds used in combination, and is suitable for various liquid crystal materials according to the purpose, and is particularly advantageous for improving the comprehensive properties of the liquid crystal materials. In addition, the liquid crystal composition has good UV, light and heat stability.
The liquid crystal composition having a negative dielectric constant of the present invention may be prepared according to a conventional method. The desired amount of the components is dissolved in the components constituting the main ingredient in a relatively low amount, usually at high temperature; the solutions of the components may also be mixed with an organic solvent, for example, acetone, chloroform or methanol, and after thorough mixing, the solvent is removed again, for example, by distillation.
The type of the conventional liquid crystal compound contained in the liquid crystal composition having a negative dielectric constant of the present invention is not limited, and any type of liquid crystal compound may be selected according to the purpose to constitute a liquid crystal mixture together with the liquid crystal compound of the present invention, and other additives in the art may be added as required. For example, polymerizable compounds, optically active components and/or stabilizers may be added in a mass content of 0 to 20%.
The above polymerizable compound has the following general formula:
Wherein,
-T 1 and-T 2 are each independently representedOr an epoxy group;
-W 1 -and-W 2 -each independently represent a single bond or an alkyl group having 1 to 8 carbon atoms;
-X 1 -and-X 2 -each independently represent a single bond, -O-, CO-, COO-, or-OCO-;
i is 0, 1 or 2;
When i is 1, -Z 1 -represents a single bond 、—O—、—CO—、—COO—、—OCO—、—CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、-C≡C-、—CH＝CH—、
When i is 2, -Z 1 -appears twice in the general formula, -Z 1 -each occurrence independently represents a single bond 、—O—、—CO—、—COO—、—OCO—、—CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、-C≡C-、—CH＝CH—、
Representation ofWherein-CH 2 -on the cyclohexyl group may be substituted by O, or representsWherein =ch-on the benzene ring may be substituted with N, H on the benzene ring may be substituted with F, or represents
When the value of i is 1, the value of i,Representation ofWherein-CH 2 -on the cyclohexyl group may be substituted by O, or representsWherein =ch-on the benzene ring may be substituted with N, H on the benzene ring may be substituted with F, or represents
When i is 2, two are included in the formulaI.e.In the general formula (iii) it occurs twice,Each occurrence is independentlyWherein-CH 2 -on the cyclohexyl group may be replaced by O, orWherein =ch-on the benzene ring may be substituted by N, H on the benzene ring may be substituted by F, or
The above optically active components are preferably:
wherein R is a halogenated or unsubstituted alkyl, alkoxy or alkenyl group having from 1 to 7 carbon atoms.
The stabilizer is preferably one or more of the compounds represented by the general formulae VI1 to VI 5.
VI1、VI2、VI3、
VI4、VI5、
In the formulas VI1 to VI5, R 9 is 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 halogenated alkyl group having 1 to 7 carbon atoms, a halogenated alkoxy group having 1 to 7 carbon atoms, or a halogenated alkenyl group having 2 to 7 carbon atoms; the alkyl, alkoxy and alkenyl groups are straight or branched alkyl, alkoxy and alkenyl groups;
Selected from the group consisting of Any one of the group consisting of.
In a preferred embodiment of the present application, the liquid crystal composition further comprises at least one polar compound and/or at least one non-polar compound. The polar compound is a positive polar compound and/or a negative polar compound, preferably a negative polar compound, the positive polar compound is selected from one or more of compounds shown in formulas X1-X105, the negative polar compound is selected from one or more of compounds shown in formulas IV 1-IV 63, the non-polar compound is selected from one or more of compounds shown in formulas V1-V33,
Wherein the positive compounds having X1 to X105 are respectively:
In the formulas X1 to X105, R 7 is H, alkyl, alkoxy, alkenyl or alkenylalkoxy having 1 to 7 carbon atoms, wherein H or CH 2 may be substituted by cyclopentyl or F; r 7 can also be cyclopentyl or cyclopentyl substituted by alkyl, alkoxy, or alkenyl groups of 1 to 7 carbon atoms; r 8 is H, F, CN, NCS, cl, OCF 3, alkyl, alkoxy, alkenyl or alkenylalkoxy having 1 to 7 carbon atoms, where H or CH2 may be substituted by cyclopentyl or F; r 8 can also be cyclopentyl or cyclopentyl substituted by alkyl, alkoxy, or alkenyl groups of 1 to 7 carbon atoms; the alkyl group having 1 to 7 carbon atoms is preferably ：-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13 or-C 7H15; the alkenyl group having 1 to 7 carbon atoms is preferably ：-CH＝CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2 or-C 3H6CH＝CHCH3; the alkoxy group having 1 to 7 carbon atoms is preferably ：-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13 or-OC 7H15; the alkenylalkoxy group having 1 to 7 carbon atoms is preferably: -och=ch 2、-OCH2CH＝CH2、-OCH2CH＝CHCH3 or-OCH 2CH＝CHC2H5;X9 and X 10 are each independently selected from H or F.
The polar liquid crystal compounds X1 to X105 have positive dielectric anisotropy, can be combined with the liquid crystal composition to form a positive dielectric liquid crystal mixture, can also be combined with the liquid crystal composition to form a liquid crystal mixture with negative dielectric property, and can be used for adjusting parameters such as dielectric constant, refractive index, rotational viscosity, elastic coefficient, clearing point temperature and the like of a system. And on the basis of the composition, the positive dielectric liquid crystal compound with larger structural difference is added, so that the melting point is reduced, the low-temperature reliability of a liquid crystal mixture is improved, the lower limit temperature of a liquid crystal medium is reduced, and the working temperature range of the liquid crystal medium is widened.
The negative polarity compounds having IV1 to IV63 are respectively:
In the formulas IV1 to IV63, R 3 and R 4 are each independently H, alkyl having 1 to 7 carbon atoms, alkoxy having 1 to 7 carbon atoms, alkenyl having 2 to 7 carbon atoms or alkenylalkoxy having 2 to 7 carbon atoms, or alkyl having 1 to 7 carbon atoms, alkoxy having 1 to 7 carbon atoms, alkenyl having 2 to 7 carbon atoms or alkenylalkoxy having 2 to 7 carbon atoms, substituted by cyclopentyl or F for H or CH 2, or are cyclopentyl, oxycyclopentyl Oxymethyl cyclopentylOxoethyl cyclopentylOr C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, oxyethylcyclopentyl; the alkyl group with 1-7 carbon atoms is -CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13 or-C 7H15; the alkenyl group having 2 to 7 carbon atoms is preferably -CH＝CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2 or-C 3H6CH＝CHCH3; the alkoxy group having 1 to 7 carbon atoms is preferably -OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13 or-OC 7H15; the alkenylalkoxy group having 2 to 7 carbon atoms is preferably-och=ch 2、-OCH2CH＝CH2、-OCH2CH＝CHCH3 or-OCH 2CH＝CHC2H5.
The polar liquid crystal compounds IV 1-IV 63 have negative dielectric anisotropy, and the negative dielectric constant liquid crystal compounds are characterized by having larger dipole effect in the direction vertical to the long axis of molecules, so that the corresponding component of dielectric constant in the vertical direction is relatively larger, namely, the liquid crystal compounds have higher vertical dielectric constant epsilon ⊥, liquid crystal molecules tend to be distributed along the direction vertical to an electric field, and the negative liquid crystal materials are all arranged on a horizontal plane under the fringe electric field, and the pretilt angle distribution is more uniform than that of positive material, so that the liquid crystal materials have higher light transmittance and wide viewing angle; in addition, the addition of the liquid crystal compound with negative dielectric constant can improve the bending elastic coefficient K 33 of the system, so that the light transmittance of the whole system is improved, the energy conservation is facilitated, and the contrast ratio is improved. In addition, the addition of different liquid crystal compounds is beneficial to improving the low-temperature reliability of the liquid crystal medium, reducing the lower limit temperature of the liquid crystal medium and widening the working temperature range of the liquid crystal medium.
The nonpolar liquid crystal compound is selected from one or more of compounds shown in formulas V1-V33; wherein, the formulas V1 to V33 are as follows:
In the formulas V1 to V33, R 5、R6 is independently selected from H, F, alkyl with 1 to 7 carbon atoms, alkoxy with 1 to 7 carbon atoms, alkenyl with 2 to 7 carbon atoms or alkenylalkoxy with 2 to 7 carbon atoms, or is cyclopentyl substituted by alkyl with 1 to 7 carbon atoms, alkoxy with 1 to 7 carbon atoms or alkenyl with 2 to 7 carbon atoms, wherein H or CH 2 is substituted by cyclopentyl or F; the alkyl group with 1-7 carbon atoms is -CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13 or-C 7H15; the alkenyl group having 2 to 7 carbon atoms is preferably -CH＝CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2 or-C 3H6CH＝CHCH3; the alkoxy group having 1 to 7 carbon atoms is preferably -OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13 or-OC 7H15; the alkenylalkoxy group having 2 to 7 carbon atoms is preferably-och=ch 2、-OCH2CH＝CH2、-OCH2CH＝CHCH3 or-OCH 2CH＝CHC2H5.
The above-mentioned nonpolar liquid crystal compounds V1 to V6 have a lower rotational viscosity γ 1, the response time of which is proportional to the rotational viscosity γ 1, meaning that the lower the value of the rotational viscosity γ 1, the lower the response time, the faster the response speed, and the liquid crystal mixtures having the above-mentioned nonpolar liquid crystal compounds V1 to V6 can be used for producing a liquid crystal medium having a rapid response. The nonpolar liquid crystal compounds V7 to V17 have higher clearing point temperature and are mainly used for adjusting the T NI value of a system, so that the liquid crystal mixture with the nonpolar liquid crystal compounds V7 to V17 is beneficial to improving the upper limit temperature of the use of a liquid crystal medium and widening the working temperature range of the liquid crystal medium. The nonpolar liquid crystal compounds V18 to V24 have a terphenyl structure, the nonpolar liquid crystal compounds V25 to V30 have an alkynyl benzene structure, are all large conjugated system compounds, are favorable for increasing the optical anisotropy Δn value of the system, generally have a value of the optical path difference d·Δn which is predetermined, the higher the Δn value is, the lower the d value is, and the response speed is inversely proportional to the d value, so that the response speed of the liquid crystal mixture having the nonpolar liquid crystal compounds V18 to V30 has a more desirable value. The nonpolar liquid crystal compounds V31 to V33 have a larger elastic coefficient, and the response time is inversely proportional to the elastic coefficient, which means that the higher the elastic coefficient value is, the lower the response time is, and the faster the response speed is, so that the liquid crystal mixture having the nonpolar liquid crystal compounds V31 to V33 has a more desirable response speed.
The liquid crystal composition has the outstanding characteristics that the general formula I and the general formula II can be added in a small amount to obtain proper dielectric constant and optical characteristics, so that the overall viscosity of the liquid crystal composition can be reduced, and the response speed can be increased. Preferably, at least one low-viscosity nonpolar liquid crystal compound with a structural formula of III1 is added into the liquid crystal composition to obtain a low-viscosity liquid crystal composition, so that the response speed is improved. Further preferred is a compound wherein Y 2 is propyl and Y 2' is vinyl. The liquid crystal composition is preferably applied to a vertical alignment display (VA), a Polymer Stabilized Vertical Alignment (PSVA), or a Fringe Field Switching (FFS) mode liquid crystal display.
The content of the liquid crystal compound in the liquid crystal composition can be adjusted according to the performance requirements of the liquid crystal material. In order to obtain more suitable liquid crystal width, higher dielectric anisotropy value, smaller rotational viscosity and suitable elasticity coefficient K, which is more beneficial to improving the response speed of the liquid crystal material, reducing the threshold voltage and improving the intersolubility of the liquid crystal material, in a preferred embodiment of the invention, the weight content of the liquid crystal compound with the general formula I in the liquid crystal composition is 0.1-75%, preferably 0.1-50%, and more preferably 0.1-30%; the liquid-crystalline compound having the general formula II is contained in an amount of 0.1 to 75% by weight, preferably 0.1 to 50% by weight, more preferably 0.1 to 30% by weight; the liquid-crystalline compound having the general formula III is contained in an amount of 0.1 to 75% by weight, more preferably 0.1 to 50% by weight. The remaining ingredients may be added in accordance with the teachings of the present invention as set forth above. The mass fraction of the polar liquid crystal compound is preferably 0 to 50%, and the mass fraction of the nonpolar liquid crystal compound is preferably 0 to 50%. In general, the sum of the percentages of the components is 100%.
In an exemplary embodiment of the present application, there is provided a use of the above liquid crystal composition in a liquid crystal display device. The liquid crystal composition can be applied to the preparation of liquid crystal display materials or liquid crystal display devices, and can significantly improve the performance of the liquid crystal display materials or the liquid crystal display devices.
The advantageous effects of the present invention will be further described below with reference to examples and comparative examples.
The following examples are intended to illustrate the invention without limiting it. All percentages referred to in the examples are mass percentages and temperatures are expressed in degrees celsius. The measured physicochemical parameters are expressed as follows: t NI represents a clearing point; Δn represents optical anisotropy (Δn=n e-no, 589nm, measurement temperature 25 ℃); delta epsilon represents dielectric anisotropy (delta epsilon=epsilon ∥-ε⊥,25℃);γ1 represents rotational viscosity (measured temperature 25 ℃), and T NI was measured by DSC, delta n was measured by abbe refractometer, delta epsilon and gamma 1 were measured by CV.
In various embodiments of the present invention, the liquid crystal molecular backbone nomenclature: cyclohexyl groupIndicated by the letter C; benzene ringIndicated by the letter P; cyclohexenyl groupRepresented by A; positive dielectric difluorobenzeneRepresented by Y; tetrahydropyraneRepresented by J; methoxy bridge-CH 2 O-is represented by B; difluoromethoxy bridge-CF 2 O-is represented by Q; alkynyl-C≡C-is represented by G; monofluorobenzeneIndicated by the letter H1; negative dielectric difluorobenzeneRepresented by W; difluoro dibenzofuranIndicated by the letter X1; methyl monofluorobenzeneIndicated by the letter K1.
The corresponding codes for specific group structures are shown in table 1.
TABLE 1
Each compound branch is converted to a chemical formula according to table 2 below, with the left side branch being denoted Ra and the right side branch being denoted Rb. Wherein the radicals C nH2n+1 and C mH2m+1 are straight-chain alkyl radicals having n and m carbon atoms, respectively, cp representing cyclopentylC nH2n+1 Cp represents a cyclopentyl group having a linear alkyl group of n carbon atoms. When named the main chain is preceded and the branched chain is followed, the main chain and the branched chain are separated by a "-" such asRepresented by WW-2OO 2; Represented by CCBW-3O 2; represented by PW-3O 2; Represented by X1-3O 2; Represented by X1-CpOO 2; represented by W-CpOO 4; represented by PH1P-2 Cp; Represented by PWP-1OO 2; Represented by PGW-3O 2; expressed in CC-3V.
TABLE 2
In addition, liquid crystal compoundIndicated at VHHP 1; Represented by CC31D 1; represented by PH 1P-F3.
Example 1
The liquid crystal mixture composition and the measurement parameters of example 1 are shown in Table 3.
TABLE 3 Table 3
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 11 are liquid crystal compounds with the general formula III.
Example 2
The liquid crystal mixture composition and the measurement parameters of example 2 are shown in Table 4.
TABLE 4 Table 4
Note that: the liquid crystal compounds with the numbers 1 to 6 are liquid crystal compounds with the general formula I, the liquid crystal compounds with the numbers 7 to 8 are liquid crystal compounds with the general formula II, and the liquid crystal compound with the number 9 is a liquid crystal compound with the general formula III.
Example 3
The liquid crystal mixture composition and the measurement parameters of example 3 are shown in Table 5.
TABLE 5
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 11 are liquid crystal compounds with the general formula III.
Example 4
The liquid crystal mixture composition and the measurement parameters of example 4 are shown in Table 6.
TABLE 6
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 11 are liquid crystal compounds with the general formula III.
Example 5
The liquid crystal mixture composition and the measurement parameters of example 5 are shown in Table 7.
TABLE 7
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 10 are liquid crystal compounds with the general formula III.
Example 6
The liquid crystal mixture composition and the measurement parameters of example 6 are shown in Table 8.
TABLE 8
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 11 are liquid crystal compounds with the general formula III.
Example 7
The liquid crystal mixture composition and the measurement parameters of example 7 are shown in Table 9.
TABLE 9
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 10 are liquid crystal compounds with the general formula III.
Example 8
The liquid crystal mixture composition and the measurement parameters of example 8 are shown in Table 10.
Table 10
Note that: the liquid crystal compounds with the numbers 1 to 7 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 8 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 9 to 11 are liquid crystal compounds with the general formula III.
Example 9
The liquid crystal mixture composition and the measurement parameters of example 9 are shown in Table 11.
TABLE 11
Note that: the liquid crystal compounds with the numbers 1 to 8 are liquid crystal compounds with the general formula I, the liquid crystal compound with the number 9 is a liquid crystal compound with the general formula II, and the liquid crystal compounds with the numbers 10 to 12 are liquid crystal compounds with the general formula III.
Example 10
The liquid crystal mixture composition and the measurement parameters of example 10 are shown in Table 12.
Table 12
Note that: the liquid crystal compounds with the serial numbers of 1-2 are liquid crystal compounds with the general formula I, the liquid crystal compounds with the serial numbers of 3-4 are liquid crystal compounds with the general formula II, and the liquid crystal compound with the serial number of 5 is a liquid crystal compound with the general formula III.
Comparative example 1
The liquid crystal mixture composition and the measurement parameters of comparative example 1 are shown in Table 13.
TABLE 13
Comparative example 2
The liquid crystal mixture composition and the measurement parameters of comparative example 2 are shown in Table 14.
TABLE 14
Wherein, in comparative example 1, a liquid crystal compound is usedInstead of the compound of the formula II in example 5 and the liquid-crystalline compound in comparative example 2Instead of the compound of formula II in example 6.
From the above examples, it can be found that the combination of the general formula I, the general formula II and the general formula III is advantageous to form a liquid crystal composition having a high optical anisotropy value and a high definition bright point, and can improve the viscosity of the system, adjust the dielectric constant value of the system, and improve the response speed and increase the upper limit temperature of the liquid crystal composition. When the liquid crystal composition composed of the general formula I, the general formula II and the general formula III is mixed with other liquid crystal compounds of different types, a liquid crystal mixture with proper optical anisotropy, dielectric anisotropy, high definition bright point, lower viscosity and higher elastic coefficient can be obtained, especially when III1 is more preferably a compound with Y 2 being propyl and Y 2' being vinyl, a liquid crystal mixture with low viscosity can be obtained, and the liquid crystal composition can be used for manufacturing a liquid crystal medium with quick response. The above measurement parameters are related to the physicochemical properties of all the liquid crystal compounds constituting the liquid crystal medium, and the liquid crystal composition of the present invention is mainly used for adjusting the liquid crystal parameters of the system.
From the comparison of example 5 and comparative example 1 and the comparison of example 6 and comparative example 2, it was found that when the liquid crystal compound of the general formula II was combined with the general formulae I and III, a liquid crystal composition having relatively high optical anisotropy, a high clearing point, was obtained in the case of approximate dielectric anisotropy, i.e., a liquid crystal composition having a faster response speed, a wider use temperature was obtained by combining the liquid crystal compound of the general formula I with the general formulae II and III.
Although not exhaustive of all liquid crystal compositions to be claimed, it is anticipated by those skilled in the art that, based on the embodiments disclosed above, other liquid crystal materials of the same type can be obtained in a similar manner without the need for inventive effort, simply in combination with professional attempts per se. Representative embodiments are only exemplified herein for limited space.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (2)
1. A negative liquid crystal composition, characterized in that the liquid crystal composition comprises 8.5% of components with the mass fractionLiquid crystal compound with structure, mass fraction of which is 7.3 percent and havingLiquid crystal compound with structure, mass fraction of which is 7.3 percent and havingA liquid crystal compound having a structure, the mass fraction of which is 5.0%Liquid crystal compound with structure, mass fraction of which is 9.1 percent and havingLiquid crystal compound with structure, mass fraction of which is 9.1 percent and havingLiquid crystal compound with structure, mass fraction of which is 2.7 percent and havingLiquid crystal compound with structure, mass fraction of which is 2.4 percent and has11.8% By mass of a liquid crystal compound having a structureLiquid crystal compound with structure, mass fraction of which is 7.1 percent and havingA liquid crystal compound having a structure, the mass fraction of which is 21.2%A liquid crystal compound having a structure, the mass fraction of which is 5.0%Liquid crystal compound with structure and mass fraction of 3.5% of liquid crystal compound with structureA liquid crystal compound of a structure.
2. Use of the liquid crystal composition of claim 1 in a negative display mode, which is VA or FFS display mode.
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