CN108384558A - A kind of negative type liquid crystal compound, the liquid crystal compound comprising the liquid-crystal compounds and its application - Google Patents
A kind of negative type liquid crystal compound, the liquid crystal compound comprising the liquid-crystal compounds and its application Download PDFInfo
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- CN108384558A CN108384558A CN201810229159.9A CN201810229159A CN108384558A CN 108384558 A CN108384558 A CN 108384558A CN 201810229159 A CN201810229159 A CN 201810229159A CN 108384558 A CN108384558 A CN 108384558A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 229
- 150000001875 compounds Chemical class 0.000 title claims abstract description 125
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 103
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 46
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims description 83
- 125000005819 alkenylalkoxy group Chemical group 0.000 claims description 32
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 12
- 239000012769 display material Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 29
- 230000003287 optical effect Effects 0.000 abstract description 19
- 230000004044 response Effects 0.000 abstract description 17
- 229910052799 carbon Inorganic materials 0.000 abstract 10
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 238000005259 measurement Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- -1 cyclohexyl Chemical group 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 3
- OJZVBJOHBGYINN-UHFFFAOYSA-N 1-bromo-4-ethoxy-2,3-difluorobenzene Chemical compound CCOC1=CC=C(Br)C(F)=C1F OJZVBJOHBGYINN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- MZHJJOMWLPIVFA-UHFFFAOYSA-N [Na].C#C Chemical group [Na].C#C MZHJJOMWLPIVFA-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XWGBQIRUXWSNPN-UHFFFAOYSA-N 1-cyclopentyl-4-ethynylbenzene Chemical compound C1=CC(C#C)=CC=C1C1CCCC1 XWGBQIRUXWSNPN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 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
- NVJMEQDYMUAAKL-UHFFFAOYSA-N 1-bromo-4-cyclopentylbenzene Chemical compound C1=CC(Br)=CC=C1C1CCCC1 NVJMEQDYMUAAKL-UHFFFAOYSA-N 0.000 description 1
- DYSJQUQJVBYIOT-UHFFFAOYSA-N Cc(ccc(C)c1F)c1F Chemical compound Cc(ccc(C)c1F)c1F DYSJQUQJVBYIOT-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
- LGGHDPFKSSRQNS-UHFFFAOYSA-N Tariquidar Chemical compound C1=CC=CC2=CC(C(=O)NC3=CC(OC)=C(OC)C=C3C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CN=C21 LGGHDPFKSSRQNS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 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
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 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
- 239000011232 storage material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—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
- G02F1/01—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
- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The present invention provides a kind of liquid-crystal compounds, which has general formulaWherein R1For H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；R2For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl, carbon atom number be 2~7 alkene alkoxy, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2Can be replaced by cyclopenta or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl or carbon atom number be 2~7 the cyclopenta that replaces of alkene alkoxy；A is 0,1 or 2；B is selected from 0 or 1；G is selected from singly-bound ,-COO-,-CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal compound, a liquid crystal mixture containing the liquid crystal compound and application of the liquid crystal compound.
Background
In the 60 s of the 20 th century, RCA company discovered for the first time that the light transmission mode of liquid crystal can be changed by electric stimulation, and then released the liquid crystal display technology by applying the property, the liquid crystal gradually attracted high attention of people and rapidly developed to various fields. In 1966, the industry was started with liquid crystal materials after DuPont synthesized Kevlar fibers using aramid liquid crystals. With the rapid development of decades, liquid crystal materials have been widely used in many fields such as display technology, optical storage devices, and solar cells due to their special properties, and the research range is more extensive in many fields such as chemistry, biology, and information science, and they are one of the popular and indispensable new materials in the present society.
With the change of science and technology, the requirements of people on the performance of liquid crystal materials are higher and higher. The following aspects are expected to be the main development of liquid crystal materials in the future: (1) the novel process for preparing the existing liquid crystal material is explored, the generation of byproducts and harmful substances is reduced, and the production cost is reduced; (2) the performance of the existing liquid crystal material is modified, such as reducing the requirement on the environmental temperature, improving the rich color and diversity of the liquid crystal material for display, and the like; (3) the novel functional liquid crystal material is prepared, and meets the high standard use requirements in multiple fields, such as novel liquid crystal materials for display, novel photoelectric liquid crystal storage materials in the field of information engineering, novel medicinal liquid crystal materials in the field of biological engineering and the like.
Liquid crystal displays can be divided into two driving modes, passive matrix (also called passive matrix or simple matrix) and active matrix (also called active matrix). Among them, the active matrix liquid crystal display device forms an image by changing the arrangement of a liquid crystal compound by applying a voltage to change the intensity of light emitted from a backlight, and is more and more favored because of its high resolution, high contrast, low power, thin profile, and lightweight. Active matrix liquid crystal displays can be classified into two types according to active devices: MOS (metal oxide semiconductor) or other diodes on a silicon chip as a substrate; among Thin Film Transistor (Thin Film Transistor-TFT) substrates, the most rapidly developed Thin Film Transistor-liquid crystal display (TFT-LCD) is currently used in display devices such as mobile phones, computers, liquid crystal televisions, and cameras, and is currently the mainstream product in the liquid crystal market. With the continuous development of TFT-LCD, the wide viewing angle mode has become the target of pursuit in the industry, and the mainstream wide viewing angle technologies at present 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. The negative type liquid crystal compound is excellent in color shift and influence by a vertical electric field, and exhibits higher light transmittance than the positive type material, and thus is widely used.
With the wide application of liquid crystal displays, the requirements for their performance are also increasing. The liquid crystal display requires a wider operating temperature, a faster response speed and a higher contrast ratio in terms of high image quality, and requires lower power consumption, which means that the liquid crystal display requires a lower driving voltage and a higher light transmittance. These performance improvements are not independent of the improvement in the liquid crystal material.
Disclosure of Invention
The invention aims to provide a liquid crystal compound with a negative dielectric constant, so as to improve the optical anisotropy, the rotational viscosity, the dielectric constant and the elastic coefficient characteristics of a liquid crystal material in the prior art, thereby improving the response speed of the liquid crystal material and reducing the driving voltage.
It is another object of the present invention to provide a liquid crystal mixture comprising the above liquid crystal compound.
It is a further object of the present invention to provide the use of the above liquid crystal compounds and liquid crystal mixtures.
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 compound having formula I:
wherein,
R1is H, C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkylene alkoxy;
R2h, C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, C2-C7 alkenylalkoxy, H or CH in the alkyl, alkoxy, alkenyl and alkenylalkoxy2Can be substituted by cyclopentyl, or is cyclopentyl substituted by C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkenylalkoxy;
a is 0, 1 or 2; b is selected from 0 or 1;
g is selected from the group consisting of a single bond, -COO-, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、or-CH ═ CH —;
is selected from One or more of the group consisting of;
is selected fromOne or more of the groupAnd (4) a plurality of.
According to another aspect of the present invention, there is provided a liquid crystal mixture having negative dielectric anisotropy, the liquid crystal mixture comprising at least one liquid crystal compound as described above.
According to still another aspect of the present invention, there is provided a use of the above liquid crystal compound in a liquid crystal display material or a liquid crystal display device.
According to a further aspect of the present invention, there is provided a use of the liquid crystal mixture described above in a liquid crystal display material or a liquid crystal display device.
Has the advantages that: the liquid crystal compound can effectively improve the optical anisotropy of the liquid crystal material, thereby improving the response speed of the liquid crystal material and reducing the driving voltage.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.
In one exemplary embodiment of the present invention, a liquid crystal compound is provided, the liquid crystal compound having the general formula I
In the general formula I
R1H, alkyl or alkoxy with 1-7 carbon atoms, alkenyl or alkenylalkoxy with 2-7 carbon atoms;
R2h, 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, an alkenylalkoxy group having 2 to 7 carbon atoms, the above alkyl, alkoxy, alkenyl and alkenylalkoxy groupsIn the radical H or CH2Can be substituted by cyclopentyl or cyclopentyl, or cyclopentyl substituted by alkyl with 1-7 carbon atoms, alkoxy with 1-7 carbon atoms, alkenyl with 2-7 carbon atoms or alkenylalkoxy with 2-7 carbon atoms;
a is 0, 1 or 2; b is selected from 0 or 1;
g is selected from the group consisting of a single bond, -COO-, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、or-CH ═ CH —;
is selected from One or more of the group consisting of;
is selected fromOne or more of the group consisting of.
The liquid crystal compound having a negative dielectric constant of the general formula I is white in a pure state, has a high value of optical anisotropy Deltan, and a wide nematic phase temperature range, wherein the value of optical anisotropy Deltan is adjusted according to a preset optical path difference (d.Deltan), wherein the layer thickness d is determined by the optical anisotropy △ n, and particularly at a high value of d. △ n, if the value of d is high for the optical anisotropy △ n, the value of d can be selected to be small, so that the response time has a more desirable value.
Liquid crystal compounds having a negative dielectric constant are characterized by having a large dipole effect in the direction perpendicular to the long axis of the molecule, and thus the corresponding dielectric constant has a relatively large component in the perpendicular direction, i.e., a high perpendicular dielectric constant ε⊥Thus, the dielectric anisotropy △ ε//-ε⊥Appearing as negative values. Due to the higher vertical dielectric constant epsilon⊥The liquid crystal molecules tend to be distributed along the direction vertical to the electric field, so that a lower pretilt angle is shown, the negative liquid crystal materials are arranged on a horizontal plane under the fringe electric field, and the pretilt angle is distributed more uniformly than the positive material, so that higher light transmittance and wide visual angle are shown, and the method is particularly suitable for preparing VA, PSVA and FFS type liquid crystal materials with high transmittance and wide visual angle; in addition, the addition of the liquid crystal compound with negative dielectric constant can improve the bending elastic coefficient K of the system33Therefore, the transmittance and the contrast of light in the whole system can be improved, energy conservation is facilitated, and the image display quality can be improved to better meet the performance requirement of liquid crystal display.
The liquid crystal compound with negative dielectric constant of the general formula I has another outstanding characteristic that when the compound is combined with other liquid crystal compounds, proper optical characteristics and dielectric constant can be obtained by adding a small amount of the compound. Therefore, the liquid crystal mixture obtained by combining the liquid crystal compound with the negative dielectric constant shown in the general formula I and other liquid crystal compounds has lower overall viscosity, and the reduction of the viscosity can effectively reduce the response time of the liquid crystal material and increase the response speed.
Furthermore, it will be clear to the skilled person that the above alkyl groups include not only straight chain alkyl groups but also the 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, and further to be beneficial to increasing the response speed of the liquid crystal material, reducing the threshold voltage and improving the mutual solubility of the liquid crystal material, in a preferred embodiment of the present application, the liquid crystal compound with the negative dielectric constant of the general formula I is a negative polarity liquid crystal compound having the formulas I1 to I46.
The compounds of the above general formulae I1 to I46 have the following general formulae:
wherein,
R1' is H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenylalkoxy group having 2 to 7 carbon atoms;
R2' is H, 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 an alkenylalkoxy group having 2 to 7 carbon atoms, wherein H or CH is selected from the group consisting of the alkyl group, the alkoxy group, the alkenyl group and the alkenylalkoxy group2Can be substituted by cyclopentyl or cyclopentyl, or cyclopentyl substituted by alkyl with 1-7 carbon atoms, alkoxy with 1-7 carbon atoms, alkenyl with 2-7 carbon atoms or alkenylalkoxy with 2-7 carbon atoms;
because the liquid crystal compound with the negative dielectric constant of the general formula I has a higher optical anisotropy value, when the liquid crystal compound with the general formula I is combined with other liquid crystal compounds to form a liquid crystal mixture with the negative dielectric constant, the characteristics of the liquid crystal mixture with the negative dielectric constant can be adjusted in a wider range, so that the performance requirements of more liquid crystal materials are met; in addition, the liquid crystal compound with the negative dielectric constant of the general formula I has better intersolubility when being mixed with other liquid crystal compounds, has less limitation on the types of the other liquid crystal compounds and the like used in combination, can be suitable for various liquid crystal mixtures corresponding to purposes, and is particularly beneficial to improving the comprehensive properties of the liquid crystal mixtures; in addition, the liquid crystal mixture has good UV, light and heat stability.
The liquid crystal mixture having a negative dielectric constant of the present invention can be prepared according to a conventional method. The required amount of the components is dissolved in a lower amount in the components constituting the main component, usually at an elevated temperature; it is also possible to mix the solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, thoroughly mix them and remove the solvent again, for example by distillation.
The type of the conventional liquid crystal compound contained in the liquid crystal mixture 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 the liquid crystal mixture together with the liquid crystal compound of the present invention, and other additives in the art may be added as necessary. For example, a polymerizable compound and/or a stabilizer may be added in an amount of 0 to 20% by mass.
The above polymerizable compound has the following general formula:
wherein
—T1and-T2Each independently representOr an epoxy group;
—Y1-and-Y2-each independently represents a single bond or an alkyl group having 1 to 8 carbon atoms;
—X1-and-X2-each independently represents a single bond, -O--CO-, -COO-or-OCO-;
m is 0, 1 or 2;
when m is 1, -Z1-represents a single bond, -O-, -CO-, -COO-, -OCO-, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、—CH＝CH—、
When m is 2, -Z1Two occurrences in the formula, -Z1-represents, independently for each occurrence, a single bond, -O-, -CO-, -COO-, -OCO-, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、—CH＝CH—、
To representwherein-CH on cyclohexyl2May be substituted by O, or representsWherein ═ CH-on the phenyl ring may be substituted by N, and H on the phenyl ring may be substituted by F, or
When m is 1, the compound (A) is,to representwherein-CH on cyclohexyl2May be substituted by O, or representsWherein ═ CH-on the phenyl ring may be substituted by N, and H on the phenyl ring may be substituted by F, or
When m is 2, the formula includes twoNamely, it isTwo times in the general formula (I) appear,at each occurrence independently iswherein-CH on cyclohexyl2May be substituted by O, orWherein ═ CH-on the phenyl ring may be substituted by N, and H on the phenyl ring may be substituted by F, or
The stabilizer is preferably one or more compounds represented by general formulas IV 1-IV 5.
In the formulae IV1 to IV5,
R7is a halogenated or unsubstituted alkyl, alkoxy or alkenyl group having 1 to 7 carbon atoms, which is a linear or branched alkyl, alkoxy or alkenyl group;
is composed of
Any one of the group consisting of.
In a preferred embodiment of the present application, the liquid crystal mixture further comprises at least one polar compound and/or at least one non-polar compound. The polar compound is preferably a negative compound, the negative compound is preferably one or more compounds selected from the group consisting of compounds represented by formulas II 1-II 92, and the formulas II 1-II 92 are respectively:
wherein R is3And R4Each independently represents H, 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 an alkenylalkoxy group having 2 to 7 carbon atoms, in which H or CH is present in the alkyl, alkoxy, alkenyl, and alkenylalkoxy groups2May be substituted with cyclopentyl; r3And R4Or is cyclopentyl or alkyl-, alkoxy-or alkenyl-substituted cyclopentyl of 1 to 7 carbon atoms; alkyl having 1 to 7 carbon atoms is: -CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13or-C7H15(ii) a Alkenyl having 1 to 7 carbon atoms is preferably-CH ═ CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2or-C3H6CH＝CHCH3(ii) a The alkoxy group having 1 to 7 carbon atoms is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13or-OC7H15(ii) a The alkenylalkoxy group having 1 to 7 carbon atoms is preferably-OCH2CH＝CH2、-OCH2CH＝CHCH3or-OCH2CH＝CHC2H5。
The polar liquid crystal compounds II 1-II 92 have negative dielectric anisotropy, can be combined with compounds shown in the general formula I to form a negative dielectric liquid crystal mixture, and can be used for adjusting the dielectric constant, the refractive index and the rotational viscosity gamma of a system1The matching of the parameters such as the elastic coefficient, the clearing point temperature and the like with the general formula I is favorable for improving the low-temperature reliability of the liquid crystal mixture and reducing the lower limit of the use of the liquid crystal mediumTemperature, broadens the working temperature range of the liquid crystal medium.
The nonpolar liquid crystal compound is selected from one or more compounds shown in formulas III 1-III 30; wherein the formulas III 1-III 30 are as follows:
in the formulae III1 to III30, R5、R6Is 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 an alkenylalkoxy group having 2 to 7 carbon atoms in which H or CH is present2May be substituted with cyclopentyl; r5、R6Or is cyclopentyl or alkyl-, alkoxy-or alkenyl-substituted cyclopentyl of 1 to 7 carbon atoms; the above alkyl group having 1 to 7 carbon atoms is-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13or-C7H15(ii) a The above alkenyl group having 2 to 7 carbon atoms is preferably-CH ═ CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2or-C3H6CH＝CHCH3(ii) a The above alkoxy group having 1 to 7 carbon atoms is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13or-OC7H15(ii) a The above-mentioned alkenylalkoxy group having 2 to 7 carbon atoms is preferably-OCH2CH＝CH2、-OCH2CH＝CHCH3or-OCH2CH＝CHC2H5. It will be clear to those skilled in the art that the above alkyl, alkoxy, alkenyl and alkenylalkoxy groups may be straight-chain alkyl, straight-chain alkoxy, straight-chain alkenyl, straight-chain alkenylalkoxy, or branched-chain alkyl, alkoxy, alkenyl and alkenylalkoxy groups.
The above-mentioned nonpolar liquid crystal compounds III1 to III20 have a low rotational viscosity γ1Response time and rotational viscosity gamma1Proportional ratio, indicating rotational viscosity γ1The nonpolar liquid crystal compounds III21 to III28 have a terphenyl structure, which is advantageous for increasing the optical anisotropy △ n value of the system, and in general the value of the optical path difference d. △ n is predefined, the higher the △ n value, the lower the d value, and the response speed is inversely proportional to the d value, so that the response speed of the liquid crystal mixtures having the nonpolar liquid crystal compounds III21 to III28 has more desirable valuesNIThe liquid-crystal mixtures having the abovementioned nonpolar liquid-crystal compounds III29 to III30 thus advantageously have an increased upper temperature limit for the use of the liquid-crystal media and a broadened operating temperature range for the liquid-crystal media.
The liquid crystal compound shown in the general formula I has the outstanding characteristics that when the liquid crystal compound is combined with a low-viscosity liquid crystal compound, proper optical characteristics can be obtained by adding a small amount of the liquid crystal compound, so that the overall viscosity of a liquid crystal mixture can be reduced, and the response speed is increased. Preferably, at least one low-viscosity non-polar liquid crystal compound of the structural formulas III1 to III20 is added into the liquid crystal mixture to obtain a low-viscosity liquid crystal mixture, so that the response speed is improved. It is particularly preferred to add at least one low-viscosity, nonpolar liquid-crystalline compound of the formula III5 to the liquid-crystalline mixture. The liquid crystal mixture is preferably applied in a vertical alignment display (VA), Polymer Stabilized Vertical Alignment (PSVA), or Fringe Field Switching (FFS) type liquid crystal display mode.
The content of the liquid crystal compound in the liquid crystal mixture can be adjusted according to the performance requirements of the liquid crystal material. 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, and further facilitate to increase the response speed of the liquid crystal material, reduce the threshold voltage, and improve the intersolubility of the liquid crystal material, in a preferred embodiment of the present invention, the weight content of the liquid crystal compound having the general formula I in the liquid crystal mixture is 0.1 to 75%, preferably 1 to 50%, and more preferably 1 to 30%. The remaining ingredients may be added in accordance with the teachings of the present invention as set forth above. In general, the sum of the percentage contents of the components is 100%.
In one exemplary embodiment of the present application, there is provided a liquid crystal compound represented by the general formula I above for use in a liquid crystal display device. In yet another exemplary embodiment of the present application, there is provided a liquid crystal mixture comprising a liquid crystal compound represented by formula I for use in a liquid crystal display device. When the liquid crystal compound is applied to the preparation of a liquid crystal display material or liquid crystal display equipment, the performance of the liquid crystal display material or the liquid crystal display equipment can be obviously improved.
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. The percentages referred to in the examples are percentages by mass, the temperatures being indicated in degrees Celsius. The measured physicochemical parameters are expressed as follows: t isNIIndicating clearing point, △ n indicating optical anisotropy (△ n ═ n)e-no589nm, measurement temperature 25 ℃); epsilon⊥Showing a perpendicular dielectric constant (measurement temperature 25 ℃), and △ ε showing a dielectric anisotropy (△ ε ∈ ε)∥-ε⊥，25℃)；k33Represents the flexural modulus (measurement temperature 25 ℃); gamma ray1Denotes rotational viscosity (measurement temperature 25 ℃ C.), and T is measured by DSCNI△ n measured by abbe refractometer and ε measured by CV⊥、△ε、k33And gamma1。
In various embodiments of the present invention, the liquid crystal molecular backbone is named: cyclohexyl radicalDenoted by the letter C; benzene ringDenoted by the letter P; cyclohexenyl radicalRepresented by A; difluorobenzeneExpressed as PFF; tetrahydropyransExpressed as Py; -CH2O-is represented by B; alkynyl radicalDenoted by G.
The corresponding codes for specific group structures are shown in table 1.
TABLE 1
Each compound branch was converted to a chemical formula according to Table 2 below, wherein the group CnH2n+1And CmH2m+1Is a straight-chain alkyl radical having n and m carbon atoms, respectively, CpRepresents a cyclopentyl groupCnH2n+1CpRepresents a cyclopentyl group having a straight-chain alkyl group of n carbon atoms. The main chain being before and the branches being after, e.g.
Expressed as PGPFFCpO 2;as indicated by PGPFF3CpO2,as denoted by CPGPFFCpO2,as indicated by the representation of CAPFF3O2,as represented by CBPFF3O2,denoted PPFP2 Cp.
TABLE 2
| Code | R1 | R2 |
| nm | CnH2n+1 | CmH2m+1 |
| nH | CnH2n+1 | H |
| Cpm | Cp | CmH2m+1 |
| CpH | Cp | H |
| nCpm | CnH2n+1Cp | CmH2m+1 |
| CpOm | Cp | OCmH2m+1 |
| nCpOm | CnH2n+1Cp | OCmH2m+1 |
| nCpH | CnH2n+1Cp | H |
| nOm | CnH2n+1 | OCmH2m+1 |
| nCp | CnH2n+1 | Cp |
| nmCp | CnH2n+1 | CmH2m+1Cp |
In addition, liquid crystal compoundsExpressed as 3 HHV;represented by VHHP 1;denoted CC31D 1.
Example 1
The synthesis of PGPFFCpO2 was as follows:
1. preparation of 1-cyclopentyl-4-ethynylbenzene
Under the protection of nitrogen, 22.5g (0.1mol) of p-cyclopentyl bromobenzene and 250ml of dried DMF are added into a 500ml four-neck flask, 5.04g (0.105mol) of sodium acetylene (18% xylene solution, 95% purity) is slowly added into the system, and the reaction is carried out for 24 hours at 55 ℃ until the solution turns to milk white from yellow; after the reaction is finished, chloroform is dissolved and then filtered, an organic phase is washed for 2 times, then rotary evaporation and concentration are carried out, and then normal hexane is used for passing through short silica gel, and TLC analysis is carried out to collect a pure product.
2. Preparation of 1- ((4-cyclopentylphenyl) ethynyl) -4-ethoxy-2, 3-difluorobenzene
Under the protection of nitrogen, 17.03g (0.1mol) of 1-cyclopentyl-4-ethynylbenzene, 23.2g (0.105mol) of 2, 3-difluoro-4-ethoxybromobenzene, 20.24g (0.2mol) of triethylamine, 0.85g of 5% palladium carbon, 0.85g of triphenylphosphine, 0.85g of cuprous iodide and 100ml of acetonitrile are added into the system, heated and refluxed for 3h, sampled and GC is taken out, after the reaction is finished, ethyl acetate is extracted and washed to be neutral, rotary evaporation and concentration are carried out, and then ethanol is used for recrystallization, so that 9.7g of PGPFFCpO2 with the purity of more than 99.9% can be obtained.
The composition of the liquid-crystal mixture of example 1 and the measurement parameters are shown in Table 3.
TABLE 3
Note: the liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I.
Example 2
The composition of the liquid-crystal mixture of example 2 and the measurement parameters are shown in Table 4.
TABLE 4
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 3
The composition of the liquid-crystal mixtures of example 3 and the measurement parameters are shown in Table 5.
TABLE 5
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 4
The composition of the liquid-crystal mixture of example 4 and the measurement parameters are shown in Table 6.
TABLE 6
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 5
The synthesis of PGPFF3CpO2 was as follows:
1. 1-ethynyl-4- (3-propylcyclopentyl) benzene
Under the protection of nitrogen, 22.5g (0.1mol) of p-propylcyclopentyl bromobenzene and 250ml of dried DMF are added into a 500ml four-neck flask, 5.04g (0.105mol) of sodium acetylene (18% xylene solution, 95% purity) is slowly added into the system, and the solution is reacted for 24 hours at 55 ℃ and is changed from yellow to milky white; after the reaction is finished, chloroform is dissolved and then filtered, an organic phase is washed for 2 times, then rotary evaporation and concentration are carried out, and then normal hexane is used for passing through short silica gel, and TLC analysis is carried out to collect a pure product.
2. Preparation of 1-ethoxy-2, 3-difluoro-4- ((4- (3-propylcyclopentyl) phenyl) ethynyl) benzene
Under the protection of nitrogen, 17.03g (0.1mol) of 1-ethynyl-4- (3-propylcyclopentyl) benzene, 23.2g (0.105mol) of 2, 3-difluoro-4-ethoxybromobenzene, 20.24g (0.2mol) of triethylamine, 0.85g of 5% palladium-carbon, 0.85g of triphenylphosphine, 0.85g of cuprous iodide and 100ml of acetonitrile are added into the system, heated and refluxed for 3h, sampled and GC, after the reaction is finished, ethyl acetate extraction water is washed to be neutral, rotary evaporation concentration is carried out, and recrystallization is carried out by ethanol to obtain 10.3g of PGPFF3CpO2 with the purity of more than 99.9%.
The composition of the liquid-crystal mixtures of example 5 and the measurement parameters are shown in Table 7.
TABLE 7
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 6
The composition of the liquid-crystal mixtures of example 6 and the measurement parameters are shown in Table 8.
TABLE 8
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 7
The composition of the liquid-crystal mixtures of example 7 and the measurement parameters are shown in Table 9.
TABLE 9
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 8
The composition of the liquid-crystal mixture of example 8 and the measurement parameters are shown in Table 10.
Watch 10
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 9
The composition of the liquid-crystal mixture of example 9 and the measurement parameters are shown in Table 11.
TABLE 11
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 10
The synthesis method of PPGPFFCpO2 is as follows:
1. preparation of 4-cyclopentyl-4 '-ethynyl-1, 1' -biphenyl
Under the protection of nitrogen, 30.12g (0.1mol) of 4-bromo-4 '-cyclopentyl-1, 1' -biphenyl and 250ml of dried DMF are added into a 500ml four-neck flask, 5.04g (0.105mol) of sodium acetylene (18% xylene solution, 95% purity) is slowly added into the system, and the solution is reacted for 24 hours at 55 ℃ and is changed from yellow to milky white; after the reaction is finished, chloroform is dissolved and then filtered, an organic phase is washed for 2 times, then rotary evaporation and concentration are carried out, and then normal hexane is used for passing through short silica gel, and TLC analysis is carried out to collect a pure product.
2. Preparation of 4-cyclopentyl-4 '- ((4-ethoxy-2, 3-difluorophenyl) ethynyl) -1,1' -biphenyl
Under the protection of nitrogen, 24.63g (0.1mol) of 4-cyclopentyl-4 '-ethynyl-1, 1' -biphenyl, 23.2g (0.105mol) of 2, 3-difluoro-4-ethoxy bromobenzene, 20.24g (0.2mol) of triethylamine, 0.85g of 5% palladium-carbon, 0.85g of triphenylphosphine, 0.85g of cuprous iodide and 100ml of acetonitrile are added into the system, heated and refluxed for 3h, sampled and GC, after the reaction is finished, ethyl acetate extraction water is washed to be neutral, and then rotary evaporation concentration and ethanol crystallization are carried out. Recrystallization from ethanol gave 12.2g of PPGPFFCpO2 with a purity of 99.9% or more.
The composition of the liquid-crystal mixture of example 10 and the measurement parameters are shown in Table 12.
TABLE 12
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 11
The composition of the liquid-crystal mixture and the measurement parameters of example 11 are shown in Table 13.
Watch 13
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 12
The composition of the liquid-crystal mixture and the measurement parameters of example 12 are shown in Table 14.
TABLE 14
Note: the number 1 is a liquid crystal compound having the general formula I.
Example 13
The composition of the liquid-crystal mixture and the measurement parameters of example 13 are shown in Table 15.
Watch 15
Note: the numbers 1 and 2 are liquid crystal compounds having the general formula I.
Example 14
The composition of the liquid-crystal mixture and the measurement parameters of example 14 are shown in Table 16.
TABLE 16
Note: the numbers 1 and 2 are liquid crystal compounds having the general formula I.
Example 15
The composition of the liquid-crystal mixture and the measurement parameters of example 15 are shown in Table 17.
TABLE 17
Note: the numbers 1 and 2 are liquid crystal compounds having the general formula I.
Example 16
The composition of the liquid-crystal mixture and the measurement parameters of example 16 are shown in Table 18.
Watch 18
Note: the numbers 1, 2 and 3 are liquid crystal compounds having the general formula I.
Comparative example 1
The composition of the liquid crystal mixture of comparative example 1 and the measurement parameters are shown in Table 19.
Watch 19
Comparative example 2
The composition of the liquid crystal mixture of comparative example 2 and the measurement parameters are shown in Table 20.
Watch 20
Wherein, in comparative example 1, the compound is a liquid crystal compoundInstead of that in example 1And comparative example 2 using a liquid crystalline compoundInstead of that in example 12
From the above examples, it can be seen that the liquid crystal compounds of formula I are particularly useful for increasing the optical anisotropy value of the system, and can reduce the viscosity of the system and increase the bending elastic coefficient K of the system33And a perpendicular dielectric constant ε⊥Thereby improving the response speed, improving the penetration rate of light in the whole system, being beneficial to energy saving and being beneficial to improving the contrast. When the liquid crystal compound of the general formula I is mixed with other liquid crystal compounds of different types, a liquid crystal mixture with higher optical anisotropy, high clearing point, lower viscosity and higher elastic coefficient can be obtained, and particularly when the liquid crystal compound is mixed with a nonpolar liquid crystal compound (such as a nonpolar liquid crystal compound coded by 3 HHV) with the general formula III5, the liquid crystal mixture with low viscosity can be obtained, and the liquid crystal mixture can be used for manufacturing liquid crystal media with quick response. The above-mentioned measured parameters are related to the physicochemical properties of all the liquid crystal compounds constituting the liquid crystal medium, and the liquid crystal mixture of the present invention is mainly used for regulating the liquid crystal parameters of the system.
Comparison by example 1 and comparative example 1 and example 12 and comparisonThe comparison of example 2 shows that, when the liquid crystal mixture contains the liquid crystal compound of formula I, the liquid crystal mixture has relatively high optical anisotropy value and relatively low rotational viscosity, which is particularly beneficial for manufacturing liquid crystal media with fast response and for adjusting the clearing point T suitable for the systemNIBending elastic coefficient K33Perpendicular dielectric constant ε⊥And dielectric anisotropy Δ ∈ values, which are helpful for obtaining a wider operating temperature, a faster response speed, a higher contrast ratio and transmittance, and a lower power consumption.
Although the present invention is not exhaustive of all liquid crystal mixtures claimed, it is within the scope of the skilled person to derive other analogous compounds from the above disclosed examples in a similar reaction scheme without the need for inventive work, with only the aid of his own expert 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, wherein the liquid crystal compound has the general formula I:
wherein,
R1h, alkyl or alkoxy with 1-7 carbon atoms, alkenyl or alkenylalkoxy with 2-7 carbon atoms;
R2is H, the number of carbon atoms is 1 to7 alkyl group, alkoxy group having 1 to 7 carbon atoms, alkenyl group having 2 to 7 carbon atoms, alkenylalkoxy group having 2 to 7 carbon atoms, H or CH in the alkyl group, alkoxy group, alkenyl group and alkenylalkoxy group2Can be substituted by cyclopentyl or cyclopentyl, or cyclopentyl substituted by alkyl with 1-7 carbon atoms, alkoxy with 1-7 carbon atoms, alkenyl with 2-7 carbon atoms or alkenylalkoxy with 2-7 carbon atoms;
a is 0, 1 or 2; b is selected from 0 or 1;
g is selected from the group consisting of a single bond, -COO-, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2Any one of ≡ C-or-CH ═ CH-;
is selected from One or more of the group consisting of;
is selected fromOne or more of the group consisting of.
2. The liquid crystal compound according to claim 1, wherein the general formula I is any one of general formulas I1 to I46:
wherein,
R1' is H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenylalkoxy group having 2 to 7 carbon atoms;
R2' is H, 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 an alkenylalkoxy group having 2 to 7 carbon atoms, wherein H or CH is selected from the group consisting of the alkyl group, the alkoxy group, the alkenyl group and the alkenylalkoxy group2Can be substituted by cyclopentyl or cyclopentyl, or cyclopentyl substituted by alkyl with 1-7 carbon atoms, alkoxy with 1-7 carbon atoms, alkenyl with 2-7 carbon atoms or alkenylalkoxy with 2-7 carbon atoms.
3. A liquid-crystal mixture having a negative dielectric constant, characterized in that it comprises at least one liquid-crystalline compound as claimed in claim 1 or 2.
4. The liquid crystal mixture with negative dielectric constant of claim 3, wherein the liquid crystal compound with formula I is contained in the liquid crystal mixture in an amount of 0.1-75 wt%, preferably 0.1-50 wt%, and more preferably 0.1-30 wt%.
5. Liquid crystal mixture with a negative dielectric constant according to claim 3, characterized in that it further comprises at least one polar liquid crystal compound and/or at least one non-polar liquid crystal compound;
preferably, the polar compound is a negative polarity liquid crystal compound, the negative polarity compound is one or more selected from compounds shown in formulas II 1-II 92, and the nonpolar compound is one or more selected from compounds shown in formulas III 1-III 30;
formulas II 1-II 92 are as follows:
in the formulae II1 to II92, R3And R4Each independently H, C1-7 alkyl, C1-7 alkoxy, C2-7 alkenyl or C2-7 alkenylalkoxy, or H or CH2An 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 an alkenylalkoxy group having 2 to 7 carbon atoms, which is substituted with a cyclopentyl group, or a cyclopentyl group substituted with an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms; the alkyl with 1-7 carbon atoms is-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13or-C7H15(ii) a The alkenyl group having 2 to 7 carbon atoms is preferably-CH ═ CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2or-C3H6CH＝CHCH3(ii) a The alkoxy group with 1-7 carbon atoms is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13or-OC7H15(ii) a The C2-7 alkenylalkoxy is preferably-OCH2CH＝CH2、-OCH2CH＝CHCH3or-OCH2CH＝CHC2H5；
The formulas III 1-III 30 are respectively as follows:
in the formulas III 1-III 30, R5、R6Each independently 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 an alkenylalkoxy group having 2 to 7 carbon atoms, or H or CH2An 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 an alkenylalkoxy group having 2 to 7 carbon atoms, which is substituted with a cyclopentyl group, or a cyclopentyl group substituted with an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms; the alkyl with 1-7 carbon atoms is-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13or-C7H15(ii) a The alkenyl group having 2 to 7 carbon atoms is preferably-CH ═ CH2、-CH＝CHCH3、-CH＝CHC2H5、-CH＝CHC3H7、-C2H4CH＝CH2、-C2H4CH＝CHCH3、-C3H6CH＝CH2or-C3H6CH＝CHCH3(ii) a The alkoxy group with 1-7 carbon atoms is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13or-OC7H15(ii) a The C2-7 alkenylalkoxy is preferably-OCH2CH＝CH2、-OCH2CH＝CHCH3or-OCH2CH＝CHC2H5；
Preferably, the non-polar compound is a compound of formula III 5.
6. The liquid crystal mixture with negative dielectric constant of claim 5, wherein the liquid crystal mixture comprises 0-80% by mass of the at least one polar liquid crystal compound and/or the at least one non-polar liquid crystal compound.
7. The liquid crystal mixture with the negative dielectric constant of any one of claims 3 to 6, further comprising a polymerizable compound with a mass fraction of 0 to 20%, wherein the polymerizable compound has the following general formula:
wherein
—T1and-T2Each independently representOr an epoxy group;
—Y1-and-Y2-each independently represents a single bond or an alkyl group having 1 to 8 carbon atoms;
—X1-and-X2-each independently represents a single bond, -O, -CO, -COO-or-OCO-;
—Z1-is selected from the group consisting of a single bond, -O-, -CO-, -COO-, -OCO, -CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、-C≡C-、—CH＝CH—、One or two of the group consisting of;
m is 0, 1 or 2;
each occurrence independently of the other represents-CH 2-substituted by O on unsubstituted or cyclohexyleneUnsubstituted or substituted by N for CH-on phenylene ringsWith H in the ring substituted by F
8. The liquid crystal mixture with negative dielectric constant of any one of claims 3 to 6, further comprising a stabilizer in an amount of 0 to 20% by mass, preferably the stabilizer is one or more of compounds represented by general formulas IV1 to IV 5:
wherein,
R7is 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, an aromatic hydrocarbon compound having a hydroxyl groupA 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, the alkoxy and the alkenyl are linear or branched alkyl, alkoxy and alkenyl;
is composed of Any one of the group consisting of.
9. Use of a liquid crystal compound according to claim 1 or 2 in a liquid crystal display material or a liquid crystal display device, preferably in a negative-type display mode, preferably a VA, PSVA or FFS display mode.
10. Use of a liquid-crystal mixture according to any of claims 3 to 8 in a liquid-crystal display material or a liquid-crystal display device, preferably in a negative-type display mode, preferably a VA, PSVA or FFS display mode.
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| CN115710514A (en) * | 2022-11-09 | 2023-02-24 | Tcl华星光电技术有限公司 | Liquid crystal composition and liquid crystal display panel |
| CN115926807A (en) * | 2022-08-19 | 2023-04-07 | 深圳市和力信材料有限公司 | Liquid crystal medium and application |
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Application publication date: 20180810 |