CN112300115B - Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents
Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 187
- 150000001875 compounds Chemical class 0.000 title claims abstract description 115
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 125000004432 carbon atom Chemical group C* 0.000 claims description 135
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 16
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 14
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000007547 defect Effects 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 20
- 230000000875 corresponding effect Effects 0.000 description 16
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000006750 UV protection Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- -1 fluorine-substituted carbon atom Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 206010047571 Visual impairment Diseases 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
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- QQAVJUKERMEIDB-UHFFFAOYSA-N FC=1C(=C(C=CC1OCCCC)B(O)O)O Chemical compound FC=1C(=C(C=CC1OCCCC)B(O)O)O QQAVJUKERMEIDB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZMTIHOQUIPYSQK-UHFFFAOYSA-N 4-bromo-1-ethoxy-2-fluorobenzene Chemical compound CCOC1=CC=C(Br)C=C1F ZMTIHOQUIPYSQK-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- 239000003292 glue Substances 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3494—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and oxygen atoms
-
- 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
-
- 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
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/343—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a seven-membered ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to a liquid crystal compound, a liquid crystal composition, a liquid crystal display element and a liquid crystal display containing the liquid crystal compound or the liquid crystal composition, and belongs to the field of liquid crystal display. The invention relates to a liquid crystal compound, which is shown in a formula I. The liquid crystal compound can improve the residual image defect of the liquid crystal display.
Description
Technical Field
The invention belongs to the technical field of liquid crystal display, and particularly relates to a liquid crystal compound for a liquid crystal composition, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display element or a liquid crystal display containing the liquid crystal compound or the liquid crystal composition.
Background
With the development of display technology, flat panel display devices such as liquid crystal displays (Liquid Crystal Display, LCDs) have been widely used in various consumer electronic products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and have become the mainstream of display devices, because of their advantages such as high image quality, power saving, thin body, and wide application range. The demands of liquid crystal flat panel display are increasing. Therefore, there is also a higher demand for quality characteristics of liquid crystal materials used in liquid crystal flat panel displays.
In the use process of the liquid crystal display, the liquid crystal composition is continuously influenced by light radiation and heat radiation, and meanwhile, in the manufacture process of the liquid crystal display or the liquid crystal composition, the liquid crystal composition is inevitably contacted with light and heat, and the light and the heat contact, especially the light and the high temperature of ultraviolet band, can cause the liquid crystal molecules to be negatively influenced in terms of impurities, thereby influencing the change of the anchoring capacity of the liquid crystal molecules and further influencing the display effect of the liquid crystal display.
Therefore, it is an urgent need in the art to provide a liquid crystal composition with good anti-uv and anti-high temperature capabilities, and improved residual image defects.
Disclosure of Invention
The present inventors have conducted intensive studies to overcome the above-mentioned problems of afterimage, and have found that a liquid crystal compound having excellent ultraviolet resistance and high temperature resistance, having a high voltage holding ratio, and capable of improving the afterimage defects can be provided.
The invention also provides a liquid crystal composition containing the liquid crystal compound and a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Specifically, the present invention includes the following:
in a first aspect of the present invention, there is provided a liquid crystal compound of formula I,
wherein R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; any of the foregoing R, R' -CH 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, any one or more non-adjacent-CH 2 -optionally substituted by-O-, any one or more hydrogen atoms optionally substituted by fluorine atoms;
independent representations
W 1 Represents O; w (W) 2 Represents O or S;
z represents a single bond, -CH 2 O-、-CH 2 CH 2 -；
m and n each independently represent 0 or 1.
In a second aspect of the present invention, there is provided a liquid crystal composition comprising the liquid crystal compound of the first aspect of the present invention described above.
In a third aspect of the present invention, there is provided a liquid crystal display element or a liquid crystal display comprising the liquid crystal compound as described above or comprising the liquid crystal composition as described above, the display element or display being an active matrix display element or display or a passive matrix display element or display.
The liquid crystal compound shown in the formula I has the characteristics of good ultraviolet resistance and high temperature resistance when being used in a liquid crystal composition, has high voltage retention rate, and can improve the afterimage defect. In addition, the liquid crystal composition of the invention has larger negative dielectric anisotropy and moderate optical anisotropy.
The liquid crystal display element or the liquid crystal display containing the compound or the liquid crystal composition has no residual image or unobvious residual image, low threshold voltage, moderate optical anisotropy, high voltage retention rate, good ultraviolet resistance and high temperature resistance and wide nematic phase temperature range.
Detailed Description
[ liquid Crystal Compound ]
A liquid crystal compound is represented by the formula I,
wherein R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; any of the foregoing R, R' -CH 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, any one or more non-adjacent-CH 2 -optionally substituted by-O-, any one or more hydrogen atoms optionally substituted by fluorine atoms;
independent representations
W 1 Represents O; w (W) 2 Represents O or S;
z represents a single bond, -CH 2 O-、-CH 2 CH 2 -；
m and n each independently represent 0 or 1.
The liquid crystal compound shown in the formula I has good ultraviolet resistance and high temperature resistance, has high voltage retention rate, and can improve the residual image defect. In addition, the liquid crystal compound of the present invention has a large negative dielectric anisotropy.
Alternatively, the compound of formula I is selected from the group consisting of compounds of formulas I-1 to I-14 described below,
wherein R represents a hydrogen atom,An alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; any of the foregoing R, R' -CH 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene;
independent representations
R, R' one or more of an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms being not adjacent to each other, -CH 2 Examples of the group substituted with a cyclopropylene group, a cyclobutylene group or a cyclopentylene group include a cyclopropyl group, a cyclobutylene group, a cyclopentyl group, a methylcyclopropylene group, an ethylcyclopropylene group, a propylcyclopropylene group, an isopropylcyclopropylene group, a n-butylcyclopropylene group, an isobutylcyclopropylene group, a tert-butylcyclopropylene group, a methylcyclobutylene group, an ethylcyclobutylene group, a propylcyclobutylene group, an isopropylcyclobutylene group, a n-butylcyclobutylene group, an isobutylcyclobutylene group, a tert-butylcyclobutylene group, a methylcyclopentylene group, an ethylcyclopentylene group, a propylcyclopentylene group, an isopropylcyclopentylene group, a n-butylcyclopentylene group, an isobutylcyclopentylene group and the like.
Alternatively, the compound of formula I is selected from the group consisting of compounds of formulas I-1-1 through I-12-4 described below,
[ liquid Crystal composition ]
The liquid crystal composition according to an embodiment of the present invention contains the liquid crystal compound represented by formula I. The liquid crystal composition may contain other compounds and other additives in addition to the liquid crystal compound represented by formula I. The liquid crystal composition has the characteristics of good ultraviolet resistance and high temperature resistance, has high voltage retention rate, and can improve the residual image defect. In addition, the liquid crystal composition of the invention has larger negative dielectric anisotropy and moderate optical anisotropy.
The liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by the following formula II and one or more compounds represented by the following formula III,
in the formula II, R 1 、R 2 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
each independently represents->
In the formula III, R 3 、R 4 Each 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 carbon atom having 1 to 10 carbon atomsAlkoxy, alkenyl having 2 to 10 carbon atoms, fluorine-substituted alkenyl having 2 to 10 carbon atoms, alkenyloxy having 3 to 8 carbon atoms or fluorine-substituted alkenyloxy having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH(s) 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -、-OCH 2 -or-CH 2 O-；
Each independently represents a representation
m 1 Represents 1 or 2; n is n 1 Representing 0, 1 or 2.
By combining the compound shown in the formula II, the compound shown in the formula III and the compound shown in the formula I in the invention in the liquid crystal composition, the beneficial effects of improving the intersolubility and the response speed of the liquid crystal composition are obtained.
R as in the aforementioned formula III 3 、R 4 One or more non-adjacent-CH in the alkyl group having 1 to 10 carbon atoms 2 Examples of the group substituted by a cyclopropylene group, a cyclobutylene group or a cyclopentylene group include a cyclopropyl group, a cyclobutylene group, a cyclopentyl group, a methylcyclopropylene group, an ethylcyclopropylene group, a propylcyclopropylene group, an isopropylcyclopropylene group, a n-butylcyclopropylene group, an isobutylcyclopropylene group, a tert-butylcyclopropylene group, a methylcyclobutylene group, an ethylcyclobutylene group, a propylcyclobutylene group, an isopropylcyclohexylene group, a n-butylcyclohexylene group, an isobutylcyclobutylene group, a tert-butylcyclohexylene group, a methylcyclopentylene group, an ethylcyclopentylene group, a propylcyclopentylene group, an isopropylcyclopentylene group, a n-butylcyclopentylene group, an isobutylcyclopentylene groupCyclopentylene, and the like.
The liquid crystal composition of the present invention is preferably a negative dielectric anisotropic liquid crystal composition.
In the liquid crystal composition of the invention, the addition amount (mass ratio) of the compound shown in the formula I in the liquid crystal composition is 1-30%, preferably 1-15%; the addition amount (mass ratio) of the compound shown in the formula II in the liquid crystal composition is 15-60%, preferably 20-40%; the amount of the compound represented by formula III added to the liquid crystal composition (mass ratio) is 20 to 60%, preferably 30 to 50%.
Alternatively, the compound of formula II is selected from the group consisting of compounds of formulas II-1 to II-17,
alternatively, the compound of formula III is selected from the group consisting of compounds of formulas III-1 to III-15,
wherein R in the compounds of the formulae III-1 to III-15 3 、R 4 R in the compound represented by the formula III 3 、R 4 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more of the non-adjacent-CH groups in the radicals shown 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene.
In some embodiments, the liquid crystal composition of the present invention may optionally further comprise one or more compounds of formula IV,
wherein R is 5 、R 6 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more non-adjacent-CH(s) 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene; w represents O or S.
The liquid crystal composition has larger negative dielectric anisotropy by combining the compounds shown in the formula IV, so that the driving voltage of the device is reduced.
In the case where the compound represented by the formula IV is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula IV to be added to the liquid crystal composition may be 1 to 15%, preferably 2 to 10%.
Preferably, the compound of formula IV is selected from the group consisting of compounds of formulas IV-1 to IV-4,
wherein R is 61 Represents an alkyl group having 2 to 6 carbon atoms.
In some embodiments, the liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by formula V,
wherein R is 7 、R 8 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
each independently represents->
Alternatively, the compound of formula V is selected from the group consisting of compounds of formulas V-1 to V-4,
wherein R is 71 、R 81 Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; among them, the alkenyl group having 2 to 6 carbon atoms includes, for example, vinyl group, 2-propenyl group, and 3-pentenyl group. R is R 82 An alkoxy group having 1 to 5 carbon atoms.
The amount of the compound of formula V added to the liquid crystal composition (mass ratio) may be 1 to 30%, preferably 5 to 20%.
By using the compound represented by formula v in combination in the liquid crystal composition of the present invention, the advantageous effects of an increase in optical anisotropy Δn and a decrease in rotational viscosity are obtained.
In the liquid crystal composition of the present invention, optionally, various functional dopants may be added, and when the dopants are contained, the content of the dopants is preferably 0.01 to 1% by mass based on the liquid crystal composition, and examples of the dopants include antioxidants, ultraviolet absorbers, and chiral agents.
Examples of the antioxidant and the ultraviolet absorber include,
t 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.
Alternatively, the liquid crystal display element or liquid crystal display is preferably an active matrix liquid crystal display element or liquid crystal display.
The liquid crystal display element or the liquid crystal display containing the compound or the liquid crystal composition has no afterimage or unobvious afterimage, low threshold voltage, moderate optical anisotropy, high voltage retention rate, good ultraviolet resistance and high temperature resistance and wide nematic phase temperature range.
The structure of the liquid crystal display element or the liquid crystal display according to the present invention is not limited as long as the compound represented by the formula I according to the present invention is contained in the liquid crystal composition used in the liquid crystal display element or the liquid crystal display according to the present invention, and a person skilled in the art can select a suitable structure of the liquid crystal display element or the liquid crystal display according to the desired performance.
As an embodiment of the liquid crystal display of the present invention, for example, the following structure is given: the liquid crystal display device comprises a first substrate, a second substrate and a liquid crystal composition arranged between the first substrate and the second substrate, wherein the first substrate and the second substrate are arranged in parallel and opposite to each other, an alignment layer is arranged on one side, close to the liquid crystal composition, of the first substrate and the second substrate, a common electrode is arranged on the first substrate, a pixel electrode is arranged on the second substrate, and spacers are scattered between the first substrate and the second substrate.
As a method for manufacturing the liquid crystal display of the present invention, a person skilled in the art can select an appropriate method to manufacture according to common knowledge in the art. As an example of the method for producing a liquid crystal display of the present invention, for example, a production method comprising the steps of:
uniformly coating alignment materials on the surfaces of the first substrate and the second substrate, wherein polyimide can be selected as the alignment materials, and heating and curing the uniformly coated alignment materials at the heating temperature of 210-250 ℃ to form an alignment layer;
dispersing spacers on the surface of the second substrate, coating frame glue along the edge of the first substrate, and curing at 100-150 ℃;
the first substrate and the second substrate are oppositely arranged and are bonded to form a structure with an interlayer space;
the liquid crystal composition is injected into the interlayer space between the first substrate and the second substrate, and is sealed and cured, so that the liquid crystal composition is sealed between the first substrate and the second substrate.
Examples
In order to more clearly illustrate the present invention, the present invention will be further described with reference to preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and that this invention is not limited to the details given herein.
In the invention, the preparation method is a conventional method unless specified otherwise, the raw materials used can be obtained from the disclosed commercial path unless specified otherwise, the percentages refer to mass percentages, the temperature is in degrees centigrade (DEG C), the liquid crystal compound is also a liquid crystal monomer, and the specific meanings and testing conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is tested by DSC quantification;
Δn represents optical anisotropy, Δn=n e -n o Wherein n is o Refractive index of ordinary ray, n e The refractive index of the extraordinary ray is 25+/-2 ℃ and is measured by an Abbe refractometer at 589 nm;
delta epsilon represents dielectric anisotropy, delta epsilon=epsilon ∥ -ε ⊥ Wherein ε is ∥ For dielectric constant parallel to the molecular axis ε ⊥ For the dielectric constant perpendicular to the molecular axis, the test conditions are 25+/-0.5 ℃,1KHz, 20-micrometer parallel boxes, INSTEC, ALCT-IR1 test;
VHR represents a voltage holding ratio (%), and the test conditions were 20±2 ℃, voltage ±5V, pulse width 10ms, and voltage holding time 16.7ms. The test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
residual image: the residual image of the liquid crystal display device was obtained by displaying a predetermined fixed pattern in the display area for 1000 hours, and then evaluating the residual level of the fixed pattern by visual inspection when the full-screen uniform display was performed.
No residue
The level of O with little residue is allowable
Delta has residues at an unacceptable level
X has residues, quite poor
The preparation method of the liquid crystal composition comprises the following steps: and weighing all the liquid crystal monomers according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker with all the liquid crystal monomers on a magnetic stirring instrument, heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The structures of the liquid crystal monomers used in the examples of the present invention are represented by codes, and the codes of the liquid crystal ring structures, the terminal groups and the linking groups are represented by the following tables 1 and 2.
Table 1: corresponding code of ring structure
/>
Table 2: corresponding codes of end groups and linking groups
Examples:
the code is CC-Cp-V1;
the code is PGP-Cpr1-2;
the code is CPY-2-O2;
the code is CCY-3-O2; />
The code is COY-3-O2;
the code is CCOY-3-O2;
the code is Sb-CpO-O4;
the code is Sc-CpO-O4;
the code is Sb-CpB-O4;
the code is Sc-CpB-O4;
the code is COSd-2-3.
[ liquid Crystal Compound ]
The compounds of formula I of the present invention can be synthesized according to the following scheme:
the progress of the reaction is generally monitored by TLC, the finishing work-up of the reaction is generally washing with water, extraction, combining the organic phases, drying, evaporating the solvent under reduced pressure, and recrystallization, column chromatography, as will be apparent to those skilled in the art, and the invention can be practiced as described below
Wherein R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; any-CH in said R, R 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, any one or more non-adjacent-CH 2 -optionally substituted by-O-, any one or more hydrogen atoms optionally substituted by fluorine atoms;
independent representations W 1 Represents O; w (W) 2 Represents O or S; z represents a single bond, -CH 2 O-、-CH 2 CH 2 -; m and n each independently represent 0 or 1.
Example 1
The structural formula of the liquid crystal compound is shown in the following formula I-1-2:
the preparation route is as follows:
step 1: intermediate 1-a
46g (0.21 mol) of 4-bromo-2-fluoro-ethoxybenzene, 150mL of tetrahydrofuran and stirring are added into a 1L three-necked flask, nitrogen is filled to replace air, the flask is placed in a low-temperature tank, liquid nitrogen is used for cooling, 200mL (0.23 mol) of 2.5M lithium diisopropylamine petroleum ether solution is dropwise added when the temperature is reduced to minus 78 ℃, after half an hour of reaction, 25mL of tetrahydrofuran solution of 27g (0.25 mol) of trimethyl borate is still dropwise added at minus 78 ℃ after half an hour of reaction, a transparent solution is obtained after half an hour of reaction, a low-temperature tank is removed, 100mL of hydrochloric acid is poured into 750mL of deionized water for hydrolysis when the temperature is naturally increased to minus 20 ℃, liquid separation is carried out, the aqueous phase is extracted once by 500mL of ethyl acetate, and organic layers are combined and water is washed to be neutral. The solvent was distilled off under reduced pressure, 150ml of petroleum ether was added thereto, heated to boil, and after cooling, 45g of white solid (1-a) was obtained by filtration, yield: 83%.
Step 2: intermediate 1-b
45g (0.17 mol) (1-a) and 300mL tetrahydrofuran are added into a 1L three-port bottle, stirred until the tetrahydrofuran is fully dissolved, and 60g hydrogen peroxide is added, stirred uniformly, heated and refluxed for 7 hours; the reaction was stopped, cooled to room temperature, 300ml of dichloromethane was added, the liquid separated by shaking, the aqueous layer was extracted with 300ml of 2 dichloromethane, the dichloromethane was combined, washed with 300ml of 2 saturated aqueous sodium chloride solution, dried over 25g of anhydrous sodium sulfate and the solution was dried to give 35g of pale yellow liquid, GC:94.2% and 88% yield.
Step 3: intermediate 1-c
33g (0.14 mol) (1-b), 28g (0.14 mol) 3-fluoro-2-hydroxy-4-propylphenylboronic acid, 43g (0.31 mol) potassium carbonate, 300ml toluene and 100ml pure water are added into a 1L three-necked flask, stirred until the mixture is fully dissolved, 0.05g Pd-132 is added under the protection of nitrogen, and the mixture is heated and refluxed for 5 hours; stopping the reaction, adding 300ml of pure water, stirring and separating, extracting the water layer with 200ml of X2 toluene, combining the organic layers, washing with 300ml of X2 saturated saline, drying the solvent by spin-drying under reduced pressure, adding 100g of petroleum ether into the obtained liquid, stirring uniformly, recrystallizing at-20 ℃ to obtain white solid (1-c) 35g, GC:99.0% and 81% yield.
Step 4: compounds of formula (I)
31g (0.10 mol) (1-c), 0.2L of dried DMF and inert gas are added into a 1L three-mouth bottle, 0.22mol of NaH are added in batches, the mixture is reacted for 1 hour at room temperature after the addition, 0.11mol of bromochloromethane is added dropwise, and the reaction is carried out at room temperature overnight; pouring the reaction solution into 0.4L saturated sodium chloride aqueous solution for hydrolysis, separating the solution, extracting with ethyl acetate, washing with water, passing through a silica gel column, concentrating, recrystallizing to obtain a compound, and performing GC:98.6% and 41% yield.
The physical parameters of the liquid crystal compounds shown in the formula I-1-2 are as follows:
Δε[1KHz,25℃]：-10.6；Δn[589nm,25℃]：0.195；Cp：49℃。
example 2
The structural formula of the liquid crystal compound is shown as the following formula I-2-1:
the preparation route is as follows:
step 1:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 2-a was synthesized:
step 2:
starting from 2-a, the following compound of formula 2-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 2-b and 3-fluoro-2-hydroxy-4-propylphenylboronic acid, the following compounds of formula 2-c were synthesized with reference to step 3 in example 1:
step 4:
starting from 2-c, the following compound of formula I-2-1 was synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compound shown in the formula I-2-1 are as follows:
Δε[1KHz,25℃]：-8.6；Δn[589nm,25℃]：0.146；Cp：99℃。
example 3
The structural formula of the liquid crystal compound is shown as the following formula I-2-4:
the preparation route is as follows:
step 1:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 3-a was synthesized:
step 2:
starting from 3-a, the following compound of formula 3-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 3-b and 3-fluoro-2-hydroxy-4-butoxyphenylboronic acid, the following compound of formula 3-c was synthesized with reference to step 3 in example 1:
step 4:
starting from 3-c, the following compounds of formula I-2-4 were synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compounds of the formula I-2-4 are as follows:
Δε[1KHz,25℃]：-8.8；Δn[589nm,25℃]：0.316；Cp：90℃。
example 4
The structural formula of the compound is shown as the following formula I-4-1:
the preparation route is as follows:
step 1:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 4-a was synthesized:
step 2:
starting from 3-a, the following compound of formula 4-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 4-b and 3-fluoro-2-hydroxy-4-propylphenylboronic acid, the following compound of formula 4-c was synthesized with reference to step 3 in example 1:
/>
step 4:
starting from 4-c, the following compound of formula I-4-1 was synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compound shown in the formula I-4-1 are as follows:
Δε[1KHz,25℃]：-11.4；Δn[589nm,25℃]：0.195；Cp：115℃。
example 5
The structural formula of the liquid crystal compound is shown as the following formula I-4-4:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 5-a was synthesized:
step 2:
starting from 5-a, the following compound of formula 5-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 5-b and 3-fluoro-2-hydroxy-4-butoxyphenylboronic acid, the following compound of formula 5-c was synthesized with reference to step 3 in example 1:
step 4:
starting from 5-c, the following compounds of formula I-4-4 were synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compounds of formula I-4-4 are as follows:
Δε[1KHz,25℃]：-15.6；Δn[589nm,25℃]：0.205；Cp：110℃。
example 6
The structural formula of the compound is shown as the following formula I-11-2:
the preparation route is as follows:
step 1:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 6-a was synthesized:
step 2:
starting from 6-a, the following compound of formula 6-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 6-b and 3-fluoro-2-mercapto-4-butoxyphenylboronic acid, the following compounds of formula 6-c were synthesized with reference to step 3 in example 1:
step 4:
starting from 6-c, the following compound of formula I-11-2 was synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compound shown in the formula I-11-2 are as follows:
Δε[1KHz,25℃]：-15.6；Δn[589nm,25℃]：0.225；Cp：128℃。
example 7
The structural formula of the compound is shown as the following formula I-12-2:
/>
the preparation route is as follows:
step 1:
to be used forIs replaced by->Referring to step 1 in example 1, the following compound of formula 7-a was synthesized:
step 2:
starting from 7-a, the following compound of formula 7-b was synthesized with reference to step 2 in example 1:
step 3:
starting from 7-b and 3-fluoro-2-mercapto-4-butoxyphenylboronic acid, the following compound of formula 7-c was synthesized with reference to step 3 in example 1:
step 4:
starting from 7-c, the following compound of formula I-12-2 was synthesized with reference to step 4 of example 1:
the physical parameters of the liquid crystal compound shown in the formula I-12-2 are as follows:
Δε[1KHz,25℃]：-15.7；Δn[589nm,25℃]：0.229；Cp：190℃。
[ liquid Crystal composition ]
Example 8:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 3 below.
Table 3: formulation and corresponding Properties of the liquid Crystal composition of example 8
Example 9:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 4 below.
Table 4: formulation and corresponding Properties of the liquid Crystal composition of example 9
Example 10:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 5 below.
Table 5: formulation and corresponding Properties of the liquid Crystal composition of example 10
Example 11:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 6 below.
Table 6: formulation and corresponding Properties of the liquid Crystal composition of example 11
Example 12:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 7 below.
Table 7: formulation and corresponding Properties of the liquid Crystal composition of example 12
Example 13:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 8 below.
Table 8: formulation and corresponding Properties of the liquid Crystal composition of example 13
Comparative example 1:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 9 below.
Table 9: formulation and corresponding Properties of the liquid Crystal composition of comparative example 1
Table 10 shows the reliability test data of the liquid crystal compositions of examples 8 to 13 and comparative example 1.
The reliability of the liquid crystal composition is carried out by ultraviolet and high temperature aging tests and VHR tests, and the smaller the VHR data change of the liquid crystal composition before and after the ultraviolet and high temperature tests is, the stronger the ultraviolet and high temperature resistance is. Therefore, the uv resistance and the high temperature resistance were judged by comparing the differences of VHR data before and after the test of each example and comparative example.
First, the VHR data of the liquid crystal composition is measured as initial VHR data before the ultraviolet and high temperature aging test is performed, then the ultraviolet and high temperature aging test is performed on the liquid crystal composition, and the VHR data of the liquid crystal composition is measured again after the test.
Ultraviolet aging test: the liquid crystal composition was irradiated with 5000mJ energy under an ultraviolet lamp having a wavelength of 365 nm.
High temperature aging test: the liquid crystal composition was placed in an oven at 100 ℃ for one hour.
The smaller the change of the VHR data relative to the initial VHR data after the aging test, the stronger the ultraviolet resistance and the high temperature resistance of the liquid crystal composition are, so that the stronger the resistance of the liquid crystal composition to the damage of the external environment in the working process can be judged, and the higher the reliability of the liquid crystal composition is. In addition, the liquid crystal compositions of examples and comparative examples were poured into a liquid crystal test cell, and an afterimage test was performed, and the test results are shown in table 10 below.
Table 10: reliability test data for examples 8 to 13 and comparative example 1
Examples 8 to 13 were substantially the same as those in the liquid crystal composition of comparative example 1, but the liquid crystal composition of comparative example 1 did not contain the compound represented by formula I.
As can be seen from Table 10, the liquid crystal compositions of the examples of the present invention showed very little VHR drop after UV and high temperature, and more remarkable improvement of the residual image defect, compared with the liquid crystal composition of comparative example 1 which did not contain the liquid crystal compound of formula I.
Claims (10)
1. A liquid crystal compound is shown in formula I,
wherein R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a carbon atomAlkoxy with 1-10 sub-numbers or alkenyloxy with 3-8 carbon atoms; any-CH in said R, R 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene, any one or more non-adjacent-CH 2 -optionally substituted by-O-, any one or more hydrogen atoms optionally substituted by fluorine atoms;
independent representation->
W 1 Represents O; w (W) 2 Represents O or S;
z represents a single bond, -CH 2 O-or-CH 2 CH 2 -；
m and n each independently represent 0 or 1.
2. A liquid crystal compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the following formulas I-1 to I-14,
wherein R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R' represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; any-CH in said R, R 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene；
Independent representation->
3. A liquid crystal compound according to claim 2, wherein the compound is selected from the group consisting of compounds represented by the following formulas I-1-1 to I-12-4,
4. a liquid crystal composition comprising one or more liquid crystal compounds according to any one of claims 1 to 3.
5. The liquid crystal composition according to claim 4, further comprising one or more compounds represented by the following formula II and one or more compounds represented by the following formula III,
in the formula II, R 1 、R 2 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
each independently represents->
In the formula III, R 3 、R 4 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH(s) 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -、-OCH 2 -or-CH 2 O-；
Each independently represents->
m 1 Represents 1 or 2; n is n 1 Representing 0, 1 or 2.
6. The liquid crystal composition according to claim 5, wherein the compound represented by formula II is selected from the group consisting of compounds represented by formulas II-1 to II-17,
7. the liquid crystal composition according to claim 5 or 6, wherein the compound represented by formula III is selected from the group consisting of compounds represented by formulas III-1 to III-15,
in the formulae III-1 to III-15, R 3 、R 4 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more of the non-adjacent-CH groups in the radicals shown 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene.
8. The liquid crystal composition according to claim 5, wherein the liquid crystal composition further comprises one or more compounds represented by formula IV,
wherein R is 5 、R 6 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more non-adjacent-CH(s) 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene; w represents O or S.
9. The liquid crystal composition according to claim 5, further comprising one or more compounds of formula V,
wherein R is 7 、R 8 Each 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, a fluorine-substituted alkoxy 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 alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
each independently represents->
10. A liquid crystal display element or display comprising the compound of any one of claims 1 to 3, or the liquid crystal composition of any one of claims 4 to 9, the display element or display being an active matrix display element or display or a passive matrix display element or display.
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| JPH10236992A (en) * | 1997-02-25 | 1998-09-08 | Chisso Corp | Liquid crystal compound having negative anisotropic value of dielectric constant, liquid crystal composition containing the same and liquid crystal display element using the composition |
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| JPH10236992A (en) * | 1997-02-25 | 1998-09-08 | Chisso Corp | Liquid crystal compound having negative anisotropic value of dielectric constant, liquid crystal composition containing the same and liquid crystal display element using the composition |
| CN103339224A (en) * | 2011-04-27 | 2013-10-02 | 肯特显示器公司 | Tetraoxybiphenyl ester chiral dopants for cholesteric liquid crystal displays |
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| 《Chiral induction in nematic and smectic C liquid crystal phases by dopants with axially chiral 1,11-dimethyl-5,7-dihydrodibenz[c,e]thiepin cores》;Matthew P. Thompson等;《Journal of Materials Chemistry》;第17卷(第48期);第5068-5076页 * |
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