CN113388408A - Liquid crystal compound, liquid crystal composition and liquid crystal display element - Google Patents
Liquid crystal compound, liquid crystal composition and liquid crystal display element Download PDFInfo
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- CN113388408A CN113388408A CN202110540742.3A CN202110540742A CN113388408A CN 113388408 A CN113388408 A CN 113388408A CN 202110540742 A CN202110540742 A CN 202110540742A CN 113388408 A CN113388408 A CN 113388408A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 137
- 150000001875 compounds Chemical class 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 2
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 2
- -1 fluoro-1, 4-phenylene group Chemical group 0.000 claims description 2
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
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- 238000012360 testing method Methods 0.000 description 21
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- 238000001308 synthesis method Methods 0.000 description 20
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- KOZQNKNVCXHJPO-UHFFFAOYSA-N 5-bromopentoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCBr KOZQNKNVCXHJPO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
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- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- JKKPRDONWUMDOQ-UHFFFAOYSA-N [2,3-difluoro-4-(4-pentylcyclohexyl)phenyl]boronic acid Chemical compound C1CC(CCCCC)CCC1C1=CC=C(B(O)O)C(F)=C1F JKKPRDONWUMDOQ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
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- NOXWSLYZGNDHGB-UHFFFAOYSA-N 2-bromo-4-iodobenzaldehyde Chemical compound BrC1=CC(I)=CC=C1C=O NOXWSLYZGNDHGB-UHFFFAOYSA-N 0.000 description 1
- PEAOEILWTHNQKK-UHFFFAOYSA-N 2-bromo-4-iodophenol Chemical compound OC1=CC=C(I)C=C1Br PEAOEILWTHNQKK-UHFFFAOYSA-N 0.000 description 1
- LXYOEDGDQBDZFK-UHFFFAOYSA-N 5-bromo-2-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC(Br)=CC=C1OCC1=CC=CC=C1 LXYOEDGDQBDZFK-UHFFFAOYSA-N 0.000 description 1
- TZZAIZUHOWCIGC-UHFFFAOYSA-N 5-bromo-2-phenylmethoxyphenol Chemical compound OC1=CC(Br)=CC=C1OCC1=CC=CC=C1 TZZAIZUHOWCIGC-UHFFFAOYSA-N 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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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
- C09K19/42—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
-
- 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
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- 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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- 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)
Abstract
The invention provides a compound shown in a formula I with a self-alignment function, a negative liquid crystal composition containing the compound, and a liquid crystal display element or a liquid crystal display comprising the compound and the liquid crystal composition. The compound shown in the formula I contains two hydroxyl groups, and in the panel ODF process, due to the acting force between the hydroxyl groups and molecules on the surface of a panel (the surface of glass and the surface of an ITO electrode), the hydroxyl groups can be spontaneously arranged on panel glass or an ITO transparent electrode substrate in a standing mode, so that liquid crystal molecules close to the compound shown in the formula I are vertically arranged, and under the irradiation of UV light, a layer of polymer with a rough surface is polymerized on the substrate to achieve the effects of PI insulation and vertical alignment of the liquid crystal molecules. The compound shown in the formula I has high solubility, good ultraviolet tolerance and wide adjustable range of formed pretilt angles, can effectively improve image residue, reduces PI (polyimide) manufacturing procedures and improves production efficiency.
Description
Technical Field
The invention relates to the technical field of liquid crystal display. And more particularly to a liquid crystal compound, a liquid crystal medium containing the liquid crystal compound, a liquid crystal composition and a liquid crystal display device.
Background
With the development of Display technology, flat panel Display devices such as Liquid Crystal Display (LCD) devices have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and are becoming the mainstream of Display devices. Most of the displays in the existing market are Backlight type liquid crystal displays, that is, the displays include a Backlight Module (BM) and a liquid crystal display panel disposed on the light emitting side of the Backlight Module. The liquid crystal display panel utilizes a power plant to control the deflection of liquid crystal molecules to regulate and control the advancing direction of light rays provided by the backlight module so as to form different gray scale brightness, thereby generating pictures.
Currently, in a commonly used Liquid Crystal Display (LCD), a color film substrate and a TFT substrate are respectively provided with a layer of thin film material, which mainly functions to align liquid crystal molecules in a certain direction, and is called as an alignment layer (PI). Such alignment layers are mainly classified into a rubbing alignment type and a photo alignment type. The alignment layer has the characteristics of uniformity, adherence and stability. However, alignment layers also have certain disadvantages. Firstly, the rubbing alignment layer is easy to cause the problems of dust particles, static residues, brush marks and the like in the display process of the liquid crystal display device, so that the manufacturing yield of the liquid crystal display device is reduced; secondly, as PI has high polarity and high water absorption, PI is easy to deform in the storage and transportation process, so that the problem of uneven alignment occurs; furthermore, the price of the PI material is high, and the process of forming the PI material on the liquid crystal display panel is complex, so that the manufacturing cost of the display panel is increased; furthermore, since the PI material is usually dissolved in N-methylpyrrolidone (NMP) to prepare a PI solution, and then the PI solution is used to prepare the alignment layer, the whole process has the disadvantages of high energy consumption, environmental pollution, and easy harm to human body. The self-alignment type is used for forming a layer of polymer with a rough surface by polymerization of a self-alignment agent on a substrate under the irradiation of UV light, so that the effects of PI insulation and liquid crystal molecule alignment are achieved, although the self-alignment type can avoid the problems, the self-alignment type has limited material characteristics, poor heat resistance and aging resistance and weak capability of anchoring liquid crystal molecules, so that the display effect of a liquid crystal display device is influenced, the adjustable range of a pretilt angle formed after alignment is small, and the formed pretilt angle is not stable enough, and the factors are all technical problems which are urgently needed to be solved by the current optical alignment type.
Disclosure of Invention
The invention provides a self-aligning agent, a liquid crystal composition containing the self-aligning agent, a liquid crystal display element or a liquid crystal display comprising the self-aligning agent or the liquid crystal composition, and a PSVA liquid crystal composition especially suitable for display or TV application.
In order to achieve the above beneficial technical effects, the present invention provides an alignment agent, i.e. a compound represented by formula i:
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L1to L4Each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl;
L5、L6each independently representing F, H, Cl, -Sp-X3Or R1；
X3Represents a polymerizable functional group;
n1, n2, n3 each independently represent 0, 1, 2, 3;
The second object of the present invention is to provide a liquid crystal composition comprising the compound represented by the aforementioned formula I.
It is another object of the present invention to provide a liquid crystal display device having the above alignment film formed from the aligning agent.
Effects of the invention
The self-alignment agent disclosed by the invention contains two hydroxyl groups, and in the process of manufacturing the panel ODF, the hydroxyl groups and the molecules on the surface of the panel (the surface of glass and the surface of an ITO electrode) act with each other, so that liquid crystal molecules close to the compound disclosed as the formula I are arranged on a panel glass or an ITO transparent electrode substrate in a spontaneous standing mode, and are polymerized to form a layer of polymer with a rough surface under the irradiation of UV light, and the effects of insulating PI and aligning the liquid crystal molecules are achieved. The compound shown in the formula I has high solubility, good ultraviolet tolerance and wide adjustable range of formed pretilt angles, can effectively improve image residue, can avoid PI (polyimide) process and improve production efficiency. The compound shown in the formula I is added into an LC medium, and after the compound is introduced into an LC box, liquid crystal molecules can be pre-tilted through UV photopolymerization or crosslinking under the condition of applying voltage between electrodes.
Drawings
FIG. 1 shows the MS mass spectrum of the compound represented by formula I-1-1.
Detailed Description
The invention provides a compound shown as a formula I:
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L1to L4Each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl;
L5、L6each independently representing F, H, Cl, -Sp-X3Or R1；
X3Represents a polymerizable functional group;
n1, n2, n3 each independently represent 0, 1, 2, 3;
Preferably, the compound represented by the aforementioned formula I is selected from the group consisting of the following compounds represented by formulas I-1 to I-18:
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L2、L3、L4each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl.
Preferably, the aforementioned compounds represented by the formulae I-1 to I-18 are selected from the group consisting of the following compounds represented by the formulae I-1-1 to I-18-1:
the compound shown in the formula I contains two hydroxyl groups, and in the panel ODF manufacturing process, due to the acting force between the hydroxyl groups and molecules on the surface of a panel (the surface of glass and the surface of an ITO electrode), the hydroxyl groups can be spontaneously arranged on panel glass or an ITO transparent electrode substrate in a standing mode, so that liquid crystal molecules close to the compound shown in the formula I are vertically arranged, and under the irradiation of UV light, a layer of polymer with a rough surface is polymerized on the substrate, and the effects of PI insulation and vertical alignment of the liquid crystal molecules are achieved.
In addition, any one of the following products containing the compound shown in the formula I also belongs to the protection scope of the invention:
1) a liquid crystal composition;
2) an optically anisotropic body of a liquid crystal composition.
A liquid crystal composition, preferably comprising a compound of formula i as described above.
The liquid crystal composition of the present invention preferably comprises one or more compounds represented by formula ii:
wherein,
R2、R3each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
z represents a single bond, methyleneoxy or ethylene;
m represents 1 or 2;
The liquid crystal composition of the present invention is preferably such that the compound represented by the above formula II is selected from the group consisting of the following compounds represented by the formulae II-1 to II-8:
wherein,
R2、R3each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms.
The liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula iii and one or more compounds represented by formula iv:
wherein,
R4、R5each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
The liquid crystal composition of the present invention is preferably one in which the compound represented by the above formula III is selected from the group consisting of compounds represented by the following formulae III-1 to III-12:
the liquid crystal composition of the present invention is preferably such that the compound represented by the aforementioned formula IV is selected from the group consisting of the compounds represented by the following formulae IV-1 to IV-12:
the liquid crystal composition of the present invention preferably further comprises one or more compounds represented by formula v:
wherein,
R8、R9each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms; r8Any one or more of the radicals indicated being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
w represents O or S.
In the liquid crystal composition of the present invention, preferably, the compound represented by the formula V is selected from the group consisting of the compounds represented by the following formulas V-1 to V-12:
the liquid crystal composition of the invention preferably further comprises one or more compounds shown in formula VI,
Sp1represents a single bond or an alkylene group having 1 to 10 carbon atoms;
P1、P2each independently represents a methyl groupAcrylate or acrylate groups;
P3represents F, -CH3A methacrylate group or an acrylate group.
In the above formula VI
And P3Is indicated by a dotted line, indicating P3And
can be attached at any possible location.
In a preferred embodiment, the one or more compounds of formula VI are selected from the group consisting of compounds of formulae VI 1 to VI 4,
in addition to the aforementioned polymerizable compounds, preferably, the liquid crystal composition of the present invention may further comprise the following polymerizable compounds,
the compounds of formula VI have a somewhat lower UV sensitivity and a somewhat slower rate of polymerization than the compounds of formula I, and are relatively superficial when the polymer is actually formed. When the compound shown in the formula VI and the compound shown in the formula I are added for copolymerization, the display effect can be improved, the polymer layer provides continuous and stable pretilt, and the pretilt of liquid crystal molecules is very favorable for improving the response speed of liquid crystals under an electric field.
The liquid crystal composition provided by the invention has lower viscosity and proper elastic constant, can realize quick response, and simultaneously has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n (0.09-0.15) and high stability to heat and light. The liquid crystal display element or the liquid crystal display containing the liquid crystal composition has the advantages of wide nematic phase temperature range, low cell thickness, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
The self-aligning agent, the polymerizable compound and other additives are added on the basis of the relative mass percentage of the liquid crystal composition.
The solubility of the compounds of formula I in liquid crystals may differ slightly due to the difference in substituents, but amounts of 0.5% to 1.2% by mass can be achieved. Since the polymer formed from the compound of formula I is required to have a certain thickness to function as an insulator for PI, the compound of formula I should have sufficient solubility.
In the case of copolymerization of the compound of the formula VI with the compound of the formula I, the compound of the formula VI may be added in an amount of 0.1 to 1% by mass, preferably 0.3 to 0.8% by mass.
Preferably, dopants with various functions can also be added into the liquid crystal compound; in the liquid crystal composition, the content of the dopant is preferably 0.01-1% by mass.
Preferably, the dopant is mainly an antioxidant, a light stabilizer, or the like.
Preferably, the antioxidant is selected from one or more of the compounds represented by the following structural formula:
wherein S represents an integer of 1 to 10.
Preferably, the light stabilizer is
Wherein,
s represents an integer of 1 to 10.
[ liquid Crystal display element or liquid Crystal display ]
The invention also relates to a liquid crystal display element or a liquid crystal display comprising any one of the liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
The liquid crystal display element or liquid crystal display of the present invention is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
Specific examples of the active matrix display element or display include IPS-TFT, FFS-TFT, VA-TFT liquid crystal display elements, and other TFT displays, and SAVA-TFT liquid crystal display elements or liquid crystal displays are particularly suitable.
The liquid crystal display element or the liquid crystal display of the invention comprises the liquid crystal composition disclosed by the invention. The liquid crystal display element or the liquid crystal display has quick response speed, good reliability and better display visual angle, is mainly applied to an SAVA display mode, and is particularly suitable for curved surface display elements or displays.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method if no special description is provided, the used raw materials can be obtained from a public commercial way if no special description is provided, the percentages refer to mass percentage, the temperature is centigrade (DEG C), and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ ε represents dielectric anisotropy, and Δ ε∥-ε⊥Wherein, epsilon∥Is a dielectric constant parallel to the molecular axis,. epsilon⊥Dielectric constant perpendicular to the molecular axis, at 25 + -0.5 deg.C, 20 μm antiparallel box, INSTEC: ALCT-IR1 test;
γ1expressed as rotational viscosity (mPas) at 25 + -0.5 deg.C, 20 micron antiparallel Box, INSTEC: ALCT-IR1 test;
K11is the splay elastic constant, K33For the flexural elastic constant, the test conditions were: 25 ℃ and INSTEC, ALCT-IR1 and 20 micron antiparallel case;
VHR represents the voltage holding ratio (%), and the test conditions are 60 +/-1 ℃, the voltage is +/-5V, the pulse width is 10ms, and the voltage holding time is 1.667 ms. The testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
afterimage: the residual image of the liquid crystal display device was evaluated by visually observing the residual level of the fixed pattern in the case of performing uniform display in the full screen, on a 4-scale basis as follows, after displaying the fixed pattern for 1000 hours in the display region:
very good without residue
O very little residue at an acceptable level
The delta is remained at an unallowable level
X has a residue, is quite poor
Low-temperature observation conditions: pouring 1g of liquid crystal into a 5ml clean glass vial, sealing the vial, placing the vial into a low-temperature refrigerator at-20 ℃, and observing whether the liquid crystal is crystallized or not after 720 hours.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The method for manufacturing the liquid crystal display device in the embodiment of the invention is as follows: combining the liquid crystal groupThe compound was poured into a test cell (no polyimide alignment layer, 4 μm cell thickness, ITO electrode on substrate surface, no passivation layer). In order to achieve spontaneous vertical alignment of liquid crystal molecules, two ultraviolet irradiation processes are required: UV1, UV 2. A voltage of 15V was applied across the test cell and irradiated with an ultraviolet lamp having a dominant wavelength of 313 nm. UV 1: the irradiation time is 60s, 70s, 80s and 90s, respectively, and the irradiation intensity is 0.55mw/cm2(ii) a UV 2: the irradiation time is 90min, and the irradiation intensity is 0.20mw/cm2. After the ultraviolet irradiation process, a pretilt angle is formed on the inner side of the test box, so that liquid crystal molecules are spontaneously and vertically aligned.
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Corresponding code of the ring structure of Table 1
TABLE 2 corresponding codes for end groups and linking groups
Examples are:
The invention is illustrated below with the following specific examples:
[ liquid Crystal Compound ]
The compounds of formula i of the present invention can be synthesized according to the following scheme:
1.
2.
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L2、L3、L4each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl.
Synthesis example 1
The structural formula of the compound is shown as the following formula I-1-1,
the preparation route is as follows:
the specific operation flow of the preparation is as follows:
intermediate 1
Under the protection of nitrogen, 0.3mol of 2-benzyloxy-5-bromophenol, 0.39mol of 5-tert-butyldimethylsilyloxybromopentane, 0.39mol of anhydrous potassium carbonate and 0.8L of LDMF were put into a 2L three-necked flask and heated at 120 ℃ for reaction for 3 hours. And monitoring the reaction by a TLC plate, cooling after the reaction is finished, adding ethyl acetate, separating liquid, extracting and washing with water, spin-drying the solvent, and separating by column chromatography to obtain the compound 1 as a yellow solid. 93% for HPLC and 85% for yield Y.
Intermediate 2
Under the protection of nitrogen, 0.3mol of 4-pentylcyclohexyl 2, 3-difluorophenylboronic acid, 0.3mol of o-bromo-p-iodophenol, 0.9L of toluene, 0.3L of water, 0.36mol of potassium carbonate and 0.3g of a catalyst were put into a 2L three-necked flask, and the mixture was heated under reflux for reaction for 3 hours. Standing, separating, performing column chromatography, and recrystallizing with toluene/ethanol to obtain compound 2 as light yellow solid. 93% for HPLC and 72% for yield Y.
Intermediate 3
Under the protection of nitrogen, 0.2mol of 2, 0.22mol of 5-tert-butyldimethylsilyloxybromopentane, 0.24mol of anhydrous potassium carbonate, 0.9L of DMF, N are added into a 2L three-necked flask2The temperature is controlled at 120 ℃ for 4 hours under protection. After the reaction is finished, cooling, adding ethyl acetate, separating liquid, extracting and washing with water, spin-drying the solvent, and performing column chromatography separation to obtain a compound 3 yellow liquid, wherein HPLC (high performance liquid chromatography) accounts for 90%, and the yield Y is 70%.
Intermediate 4
Under the protection of nitrogen, 0.2mol of compound 3,1L of tetrahydrofuran and 2L of a three-necked flask are cooled to minus 78 ℃, 0.22mol of n-butyl lithium (2.5M) is dripped, after dripping is finished, trimethyl borate is dripped at minus 78 ℃ for reaction for 1 hour after stirring for 0.5 hour. After the reaction is finished, naturally heating to-20 ℃, adding 2M hydrochloric acid to adjust the pH value to be weakly acidic, separating, extracting and washing with water, spin-drying the solvent, pulping by PE, and stirring for 10min to obtain the compound 4, wherein the HPLC (high performance liquid chromatography) rate is 92%, and the yield Y is 68%.
Intermediate 5
Under the protection of nitrogen, 0.2mol of 4, 0.2mol of 2, 0.9L of toluene, 0.3L of water, 0.36mol of potassium carbonate and 0.3g of catalyst were put into a 2L three-necked flask, and the mixture was heated under reflux for 3 hours. Standing, separating, spin-drying the solvent, and performing column chromatography separation to obtain a compound 5 light yellow liquid. 93% for HPLC, and 75% for yield Y.
Intermediate 6
0.1mol of compound 5, 10g of Pd/C and 1L of THF are placed in a 2L three-necked flask, and N2Three times of replacement, H2Replacing three times, and carrying out hydrogenation debenzylation at 40 ℃ for 3 hours. After the reaction, the mixture was filtered through celite, and the filtrate was concentratedThe compound 6 was obtained in 91% by HPLC with a yield Y of 83%.
Intermediate 7
0.05mol of 6, 0.15mol of triethylamine, 0.2L of DCM and N are added into a 1L three-necked flask2Under the protection, the temperature is controlled at 0 ℃, and 0.1mol of methacrylic chloride is dripped. After dropping, the reaction was carried out at room temperature for 3 hours. After the reaction is finished, water is added for separating liquid, the water phase is extracted by DCM, the organic phases are combined, the organic phases are washed once by saturated salt water, dried by anhydrous sodium sulfate, filtered, concentrated by filtrate and separated by column chromatography to obtain the compound 7 which is light yellow liquid. HPLC: 98%, yield Y65%.
Compound I-1
0.05mol of 7, 0.5L DCM, N are put into a 500ml three-necked flask2And (3) dropwise adding boron trifluoride diethyl etherate at the temperature of 0 ℃ under protection. After dropping, the reaction was carried out at room temperature for 2 hours. After the reaction is finished, controlling the temperature to be 0 ℃, adding sodium bicarbonate and the mixture, separating liquid, extracting the water phase by DCM, combining organic phases, washing the organic phases by saturated salt water once, drying the organic phases by anhydrous sodium sulfate, filtering, concentrating the filtrate, and separating by column chromatography to obtain a white solid compound I-1-1, wherein HPLC (high performance liquid chromatography) is 99.3 percent, and the yield Y is 41 percent.
Synthesis example 2
The structural formula of the compound is shown as the following formula I-1-7,
the preparation route is as follows:
the specific operation flow of the preparation is as follows:
intermediate 1
Synthesis methods refer to the synthesis of intermediate 3 in example 1.
Intermediate 2
Synthesis methods refer to the synthesis of intermediate 3 in example 1.
Intermediate 3
Synthesis methods refer to the synthesis of intermediate 3 in example 1.
Intermediate 4
Synthesis methods refer to the synthesis of intermediate 4 in example 1.
Intermediate 5
Synthesis methods refer to the synthesis of intermediate 5 in example 1.
Intermediate 6
Synthesis methods refer to the synthesis of intermediate 6 in example 1.
Intermediate 7
Synthesis methods refer to the synthesis of intermediate 7 in example 1.
Intermediate 8
Synthetic methods reference was made to the synthesis of intermediate 8 in example 1
Compound I-1-2
Synthesis method refer to the synthesis of Compound I-1-1 in example 1.
Synthesis example 3
The structural formula of the compound is shown as the following formula I-1-7,
the preparation route is as follows:
the specific operation flow of the preparation is as follows:
intermediate 1
Under the protection of nitrogen, 0.3mol of magnesium chips are put into a 2L three-necked bottle, one particle of iodine is added, a tetrahydrofuran solution of 5-tert-butyldimethylsilyloxy bromopentane (10g of the tetrahydrofuran solution is dissolved in 100ml of THF) is added dropwise, the mixture is stirred, heated and slightly refluxed to initiate reaction, the rest 5-tert-butyldimethylsilyloxy bromopentane (total 0.36mol) is dissolved in 500ml of THF, the mixture is slowly dripped into a reaction system, after dripping is finished, the mixture is refluxed for 2 hours, 0.3mol of 2-benzyloxy-5-bromobenzaldehyde is dissolved in 400ml of THF, and the mixture is slowly dripped into the reaction system. Monitoring the reaction by a TLC plate, cooling after the reaction is finished, adding dilute hydrochloric acid to quench the reaction, and separating liquid. The aqueous phase was extracted once with ethyl acetate and the organic phases were combined, dried and spin dried. Crude compound 1 was obtained as a yellow liquid, which was taken directly to the next step.
Intermediate 2
Under the protection of nitrogen, 0.2mol of 2, 0.9LDCM is put into a 2L three-mouth bottle, triethylsilane (0.3mol) is dripped at the temperature of minus 20 ℃ for reaction for 0.5 hour, and then 0.3mol of boron trifluoride ethyl ether is dripped at the temperature of minus 20 ℃ for reaction for 1 hour after dripping. Water was added, the layers were separated and the aqueous phase was extracted once more with dichloromethane. The organic phases were combined, dried and spin dried. And (5) performing column chromatography separation to obtain a light yellow liquid of the compound 2. 93% for HPLC and 42% for yield Y.
Intermediate 3
Synthesis of intermediate 2 in route to reference Compound I-1-1
Intermediate 4
Synthesis methods refer to the synthesis of intermediate 3 in example 1.
Intermediate 5
Synthesis methods refer to the synthesis of intermediate 4 in example 1.
Intermediate 6
Synthesis methods refer to the synthesis of intermediate 5 in example 1.
Intermediate 7
Synthesis methods refer to the synthesis of intermediate 6 in example 1.
Intermediate 8
Synthesis methods refer to the synthesis of intermediate 7 in example 1.
Compounds I-1-7
Synthesis method refer to the synthesis of Compound I-1-1 in example 1.
Synthesis example 4
The structural formula of the compound is shown as the following formula I-1-8,
the preparation route is as follows:
the specific operation flow of the preparation is as follows:
intermediate 1
Synthetic methods synthesis of intermediate 1 in reference example 2
Intermediate 2
Synthesis methods refer to the synthesis of intermediate 2 in example 2.
Intermediate 3
Under the protection of nitrogen, 0.3mol of 4-pentylcyclohexyl 2, 3-difluorophenylboronic acid, 0.3mol of o-bromo-p-iodobenzaldehyde, 0.9L of toluene, 0.3L of water, 0.36mol of potassium carbonate and 0.3g of catalyst were put into a 2L three-necked flask, and the mixture was heated under reflux for 3 hours. Standing, separating, performing column chromatography, and recrystallizing with toluene/ethanol to obtain compound 3 as light yellow solid. 95% by HPLC, and 62% by yield Y.
Intermediate 4
Under the protection of nitrogen, 0.3mol of magnesium chips are put into a 3L three-necked bottle, one particle of iodine is added, a tetrahydrofuran solution of 5-tert-butyldimethylsilyloxy bromopentane (10g of the tetrahydrofuran solution is dissolved in 100ml of THF) is added dropwise, the mixture is stirred, heated and slightly refluxed to initiate reaction, the rest 5-tert-butyldimethylsilyloxy bromopentane (0.36 mol in total) is dissolved in 500ml of THF, and the mixture is slowly dripped into a reaction system, and after dripping is finished, the mixture is refluxed for 2 hours, 0.3mol of 3-800 ml of THF and is slowly dripped into the reaction system. Monitoring the reaction by a TLC plate, cooling after the reaction is finished, adding dilute hydrochloric acid to quench the reaction, and separating liquid. The aqueous phase was extracted once with ethyl acetate and the organic phases were combined, dried and spin dried. Crude compound 4 was obtained as a yellow liquid, which was taken directly to the next step.
Intermediate 5
Under the protection of nitrogen, 0.2mol of 4, 0.9LDCM is put into a 2L three-mouth bottle, triethylsilane (0.3mol) is dripped at the temperature of minus 20 ℃ for reaction for 0.5 hour, and then 0.3mol of boron trifluoride ethyl ether is dripped at the temperature of minus 20 ℃ for reaction for 1 hour after dripping. Water was added, the layers were separated and the aqueous phase was extracted once more with dichloromethane. The organic phases were combined, dried and spin dried. And (5) performing column chromatography separation to obtain a light yellow liquid of the compound 5. HPLC 94%, yield Y38%.
Intermediate 6
Synthesis methods refer to the synthesis of intermediate 4 in example 1.
Intermediate 7
Synthesis methods refer to the synthesis of intermediate 5 in example 1.
Intermediate 8
Synthesis methods refer to the synthesis of intermediate 6 in example 1.
Intermediate 9
Synthesis methods refer to the synthesis of intermediate 7 in example 1.
Compounds I-1-8
Synthesis method refer to the synthesis of Compound I-1-1 in example 1.
The present invention will be explained below with reference to the following specific examples.
Composition examples
Composition C1
The formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
TABLE 3 formulation and corresponding Properties of the liquid crystal composition of example 1
Composition C2
The formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
TABLE 4 formulation and corresponding Properties of the liquid crystal composition of example 2
Composition C3
The formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
TABLE 5 formulation and corresponding Properties of the liquid crystal composition of example 3
Composition C4
The formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
TABLE 6 formulation and corresponding Properties of the liquid crystal composition of example 4
Composition C5
The formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
TABLE 7 formulation and corresponding Properties of the liquid crystal composition of example 5
Composition C6
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 8 below.
TABLE 8 formulation and corresponding Properties of the liquid crystal composition of example 6
Contrast alignment agent:
TABLE 9 pretilt Angle test after adding self-alignment agent and polymerizable Compound (RM) to the liquid Crystal composition
TABLE 15 pretilt angle test data after UV1, UV2
The formation of the pretilt angle comprises two processes of UV1 and UV2, UV1 irradiation is firstly carried out, UV1 irradiation time is short, the pretilt angle is tested at 60s, 70s, 80s and 90s, then UV2 irradiation is carried out, the UV2 irradiation time is 90 minutes, and test data UV1 corresponds to UV 2. For example: UV1 irradiation for 60s to record the pretilt angle, UV2 irradiation for 90 minutes to record the pretilt angle; UV1 irradiation for 70s to record the pretilt angle, UV2 irradiation for 90 minutes to record the pretilt angle; by the method, 80s and 90s UV irradiation pretilt angle data are obtained, and the pretilt angle tested after 90s is the final formable pretilt angle.
Compared with a comparative example, the technical scheme of the invention has the advantages that the pretilt angle formed by the technical scheme of the invention is larger under the same condition, the pretilt angle finally formed by adding no polymerizable compound (RM) can meet the use requirement by applying the technical scheme of the invention, the pretilt angle reaches the level of the pretilt angle in the prior art, the pretilt angle obtained by the technical scheme of the invention is larger under the same condition, the adjustable range is wider, the application range is wider, a conventional quick-response display mode can be realized by especially adding only a self-aligning agent to save the polymerizable compound (RM), and the cost is greatly saved.
TABLE 15 VHR testing of liquid crystal compositions after addition of photoalignment agents and polymerizable Compounds
In the above experiment, the liquid crystal of the example and the liquid crystal of the comparative example were respectively poured into a test piece for testing, and VHR represents a voltage holding ratio (%), the test conditions were 60 ± 1 ℃, the voltage was ± 5V, the pulse width was 10ms, and the voltage holding time was 1.667 ms; the testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester; ultraviolet aging test: the liquid crystal composition was irradiated with 5000mJ energy under an ultraviolet lamp having a wavelength of 365 nm.
The reliability of the liquid crystal composition passes a VHR test after a UV illumination test, the larger the VHR data of the liquid crystal composition after the UV illumination is, the stronger the UV resistance is, the VHR of the liquid crystal composition after the UV illumination is obviously larger than that of the liquid crystal composition in a comparative example, which shows that the liquid crystal composition of the invention has strong UV resistance, thereby having strong resistance to external environment damage in the working process.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (10)
1. A liquid crystal compound, wherein the liquid crystal compound is represented by formula I:
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkyl groupAn alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L1to L4Each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl;
L5、L6each independently representing F, H, Cl, -Sp-X3Or R1；
X3Represents a polymerizable functional group;
n1, n2, n3 each independently represent 0, 1, 2, 3;
2. The liquid crystal compound of claim 1, wherein the compound of formula i is selected from the group consisting of compounds of formulae i-1 to i-18:
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, a C21-10 alkoxy or fluorine-substituted alkoxy with 1-10 carbon atoms;
X1、X2each independently representing H, R1or-Sp-OH;
sp represents a single bond, an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 2 to 10 carbon atoms or an alkyleneoxy group having 1 to 10 carbon atoms;
L2、L3、L4each independently represents F, H, Cl or R1(ii) a And L is2、L3、L4At least one represents F or Cl.
3. The compound of claim 2, wherein the compounds of formulae i-1 to i-18 are selected from the group consisting of the compounds of formulae i-1-1 to i-18-1:
4. a liquid crystal composition comprising one or more compounds of formula i according to any one of claims 1 to 3.
5. The liquid crystal composition of claim 4, wherein the liquid crystal composition comprises one or more compounds of formula II:
wherein,
R2、R3each independently represents an alkyl group having 1 to 10 carbon atoms or a carbon atomAlkoxy with the sub number of 1 to 10 or alkenyl with the carbon number of 2 to 10;
z represents a single bond, methyleneoxy or ethylene;
m represents 1 or 2;
6. The liquid crystal composition of claim 5, further comprising one or more compounds of formula III and one or more compounds of formula IV:
wherein,
R4、R5each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
7. The liquid crystal composition of claim 6, further comprising one or more compounds of formula V:
wherein,
R8、R9each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms; r8Any one or more of the radicals indicated being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
w represents O or S.
8. The liquid crystal composition of claim 4, further comprising one or more compounds of formula VI,
Sp1represents a single bond or an alkylene group having 1 to 10 carbon atoms;
P1、P2each independently represents a methacrylate group or an acrylate group;
P3represents F, -CH3A methacrylate group or an acrylate group.
9. A liquid crystal display element comprising the liquid crystal composition according to any one of claims 4 to 8, which is an active matrix display element or a passive matrix display element.
10. A liquid crystal display comprising the liquid crystal composition of any of claims 4-8, the liquid crystal display being an active matrix display or a passive matrix display.
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