CN111876163A - 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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- CN111876163A CN111876163A CN202010101339.6A CN202010101339A CN111876163A CN 111876163 A CN111876163 A CN 111876163A CN 202010101339 A CN202010101339 A CN 202010101339A CN 111876163 A CN111876163 A CN 111876163A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 163
- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000012071 phase Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical class [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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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
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a liquid crystal compound, a liquid crystal composition and a liquid crystal display element. The liquid crystal compound has a structure represented by formula (I):
wherein R is1、R2、A1And A2As defined in the specification.
Description
[ technical field ] A method for producing a semiconductor device
The present invention relates to a liquid crystal compound, a liquid crystal composition, and a liquid crystal display device, and more particularly, to a negative-type liquid crystal compound having high negative dielectric anisotropy, high clearing point temperature, and high refractive index anisotropy (anisotropy), a liquid crystal composition, and a liquid crystal display device including the liquid crystal composition.
[ background of the invention ]
Liquid crystal display devices (liquid crystal display devices) utilize electro-optical change of liquid crystal, and have advantages of small size, light weight, low power consumption, and good display quality, and thus have become mainstream in the market in recent years.
The liquid crystal display element comprises a liquid crystal composition, the liquid crystal composition comprises more than one liquid crystal compound, and in order to improve the performance of the liquid crystal display element, the liquid crystal compound has the following characteristics: (1) the chemical property and the physical property are stable; (2) has a high clearing point (nematic phase to liquid phase transition temperature); (3) the lower limit temperature of the nematic phase is low; (4) excellent compatibility with other liquid crystal compounds; (5) the absolute value of the dielectric anisotropy is large (i.e. positive type liquid crystal has high dielectric anisotropy, negative type liquid crystal has low dielectric anisotropy); (6) has relatively high optical anisotropy.
When the liquid crystal display element contains a liquid crystal compound with stable chemical properties and physical properties, the voltage holding ratio can be improved. When a liquid crystal compound having a high clearing point and a low lower limit temperature of a nematic phase is used, the temperature range of the nematic phase can be widened, the use temperature range of the liquid crystal display element can be widened, and the application range of the liquid crystal display element can be widened. When a liquid crystal compound having excellent compatibility with other liquid crystal compounds is used, the properties of the liquid crystal composition can be improved. Since it is difficult for a single liquid crystal compound to have all of the above features, the liquid crystal composition generally contains more than one liquid crystal compound, and the higher the compatibility between the liquid crystal compounds, the more favorable the uniformity and stability of the liquid crystal composition. When the liquid crystal compound with larger dielectric anisotropy is used, the threshold voltage is reduced, the power consumption of the liquid crystal display element is saved, and the response speed is improved. When a liquid crystal compound having a high optical anisotropy is used, it is helpful to improve the contrast.
It is known that when the value of the product of the cell thickness (d) constituting the liquid crystal display element and the optical anisotropy (Δ n) of the liquid crystal composition is fixed, the cell thickness (d) of the liquid crystal display element to be used can be made small when the optical anisotropy (Δ n) is large. The proper multiplication value depends on the kind of operation mode, for example, a liquid crystal display device operating with Twisted Nematic (TN) operation, and the proper multiplication value is about 0.45 μm. Since the response speed is inversely proportional to the square of the cell thickness, a liquid crystal compound having a high optical anisotropy can be used while maintaining a fixed product value and taking into account the response speed.
In view of the above, it is an objective of the related industries to improve the molecular structure of the liquid crystal compound to further improve the quality of the liquid crystal display device.
[ summary of the invention ]
An object of the present invention is to provide a liquid crystal compound which is a negative type liquid crystal compound (i.e., having a dielectric anisotropy of less than 0) and has characteristics of high negative dielectric anisotropy, high clearing point temperature, high refractive index anisotropy, and good solubility.
Another object of the present invention is to provide a liquid crystal composition, which contains the above liquid crystal compound, and thus is advantageous for reducing driving voltage and has good storage property.
It is another object of the present invention to provide a liquid crystal display device, which comprises the liquid crystal composition.
One embodiment of the present invention provides a liquid crystal compound having a structure represented by formula (I):
wherein R is1And R2Each independently is 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, R1And R2Is unsubstituted or at least one hydrogen is optionally (optionally) substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1And A2Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), or formula (iii-2):
the liquid crystal compound according to the above, wherein R in the formula (I)1And R2Each independently is an alkyl group having 1 to 5 carbon atoms, R1And R2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1Is a structure represented by the formula (i), A2Is a formula (ii) or a formula (iii)-1) or formula (iii-2).
Another embodiment of the present invention provides a liquid crystal composition comprising the liquid crystal compound described in the previous paragraph.
According to the liquid crystal composition, in the formula (I), R1And R2Each independently is an alkyl group having 1 to 5 carbon atoms, R1And R2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1Is a structure represented by the formula (i), A2Is a structure represented by the formula (ii), the formula (iii-1) or the formula (iii-2).
The content of the liquid crystal compound in the liquid crystal composition may be greater than 0 part by weight and less than 7 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
According to the liquid crystal composition, a compound shown as formula (II) or formula (III) can be further included:
wherein R is3、R4、R5And R6Each independently is 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, R3、R4、R5And R6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-. A. the3、A4And A5Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1), or formula (vi-2):
Z1and Z2Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-. n is1And n2Each of which isIndependently is 1 or 2, and when n1When 2, two A3And two Z1Can be the same or different, when n2When 2, two A5And two Z2May be the same or different.
The liquid crystal composition according to the above, wherein in the compound of formula (II), R3And R4Each independently is 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, R3And R4Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, A3And A4Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2), Z1Is a single bond, n1Is 1.
The liquid crystal composition according to the above, wherein in the compound of formula (III), R5And R6Each independently is 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, R5And R6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, A5Is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2), Z2Is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-, n2Is 1.
The content of the compound of formula (II) in the liquid crystal composition may be 25 to 65 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition. In addition, the compound of formula (III) may be contained in an amount of 30 to 70 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
The liquid crystal composition may further comprise a polymerizable compound. The polymerizable compound has a structure as shown in formula (IV):
wherein A is6、A7And A8Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (vii), formula (viii), formula (ix), formula (x) or formula (xi):
and A is6、A7And A8Is unsubstituted or at least one hydrogen may be optionally substituted by fluorine atoms, methyl or methoxy, or at least one-CH2-is optionally substituted by-O-or at least one-CH-may be substituted by-N-. Z3And Z4Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-. X1And X2Each independently a single bond, an alkyl group having 1 to 6 carbon atoms, and X1And X2At least one of-CH2-optionally substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. Y is1And Y2Each independently is a polymerizable group, wherein the polymerizable group has a structure represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6) or formula (7):
n3is an integer of 0 to 2, and when n3When 2, two A7And two Z4May be the same or different.
The liquid crystal composition according to the preceding paragraph, wherein the clearing point temperature (T) of the liquid crystal compositionni) Is 65 ℃ to 120 ℃, a dielectric anisotropy (Delta) is-2 to-8, and a refractive index anisotropy (Delta n) is 0.05 to 0.15.
In another embodiment of the present invention, a liquid crystal display device is provided, which comprises the liquid crystal composition described in the previous paragraph.
[ detailed description ] embodiments
Embodiments of the invention are discussed in more detail below. However, this embodiment may be an application of various inventive concepts, which may be embodied within various specific ranges. The specific embodiments are for purposes of illustration only and are not to be construed as limiting the scope of the disclosure.
< liquid Crystal Compound >
The liquid crystal compound has a structure shown as a formula (I):
wherein R is1And R2Each independently is 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, R1And R2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1And A2Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), or formula (iii-2):
therefore, the liquid crystal compound is a negative liquid crystal compound, has higher negative dielectric anisotropy, high clearing point temperature and high refractive index anisotropy, is stable to acid, heat and UV (ultraviolet) and has good solubility, and can improve or improve the performance of the liquid crystal composition when being applied to the liquid crystal composition.
According to the aforementioned liquid crystal compound, in the formula (I), R1And R2Each independently is an alkyl group having 1 to 5 carbon atoms, wherein R1And R2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1Is a structure represented by the formula (i), A2Is a structure represented by the formula (ii), the formula (iii-1) or the formula (iii-2).
For example, the liquid crystal compound of formula (I) may be, but is not limited to, a compound having a structure represented by any one of formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5), and formula (I-6):
< liquid Crystal composition >
The liquid crystal composition of the present invention comprises the liquid crystal compound having the structure shown in formula (I), and for the liquid crystal compound, please refer to the above description, which is not repeated herein.
According to the aforementioned liquid crystal composition, the content of the liquid crystal compound may be preferably more than 0 part by weight and less than 7 parts by weight, more preferably more than 0 part by weight and less than 5 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition, wherein if the content of the liquid crystal compound is more than 7 parts by weight, the low-temperature storage property is poor.
According to the liquid crystal composition, at least one of the compounds represented by formula (II) or formula (III) may be further included:
in the formulae (II) and (III), R3、R4、R5And R6Each independently is 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, wherein R is3、R4、R5And R6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-. A. the3、A4And A5Each independently is formula(i) A structure represented by formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2):
Z1and Z2Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-. n is1And n2Each independently is 1 or 2, and when n1When 2, two A3And two Z1Can be the same or different, when n2When 2, two A5And two Z2May be the same or different.
According to the aforementioned liquid crystal composition, the compound of formula (II) wherein R3And R4Can be respectively and independently alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, wherein R3And R4Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, A3And A4Each independently may be a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2), Z1Is a single bond, n1Is 1.
For example, the compound of formula (II) may be, but is not limited to, a compound having a structure represented by any one of formula (II-1), formula (II-2), formula (II-3), formula (II-4), formula (II-5), formula (II-6), formula (II-7), formula (II-8), formula (II-9), formula (II-10), formula (II-11), formula (II-12), formula (II-13), formula (II-14), formula (II-15), formula (II-16), (II-17), formula (II-18), and formula (II-19):
the compounds represented by the above formulae (II-1) to (II-19) may be used alone or in combination of two or more.
According to the aforementioned liquid crystal composition, the compound of formula (III) wherein R5And R6Can be respectively and independently alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, wherein R5And R6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, A5May be a structure represented by the formula (i), the formula (ii), the formula (iii-1), the formula (iii-2), the formula (iv-1), the formula (iv-2), the formula (v-1), the formula (v-2), the formula (vi-1) or the formula (vi-2), Z2Can be a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-, n2Is 1.
For example, the compound of formula (III) may be, but is not limited to, a compound having a structure as shown in any one of formula (III-1), formula (III-2), formula (III-3), formula (III-4), formula (III-5), formula (III-6), formula (III-7), formula (III-8), formula (III-9), formula (III-10), (III-11), formula (III-12), formula (III-13), formula (III-14), formula (III-15), formula (III-16), formula (III-17), formula (III-18), formula (III-19), and formula (III-20):
the compounds represented by the above formulae (III-1) to (III-20) may be used alone or in combination of two or more.
The liquid crystal composition may further include at least one of the compounds having the structures shown in the formulas (II) and (III), which means that the liquid crystal composition may include only one of the compounds having the structures shown in the formulas (II) and (III), or may include two or more of the compounds.
In the foregoing liquid crystal composition, preferably, the liquid crystal composition may include 25 to 65 parts by weight of the compound of formula (II) and 30 to 70 parts by weight of the compound of formula (III) based on 100 parts by weight of the total weight of the liquid crystal composition. More preferably, the liquid crystal composition may include 30 to 60 parts by weight of the compound of formula (II) and 35 to 67 parts by weight of the compound of formula (III) based on 100 parts by weight of the total weight of the liquid crystal composition.
The liquid crystal composition may further comprise a polymerizable compound, wherein the polymerizable compound has a structure shown in formula (IV):
in the formula (IV), A6、A7And A8Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (vii), formula (viii), formula (ix), formula (x) or formula (xi):
A6、A7and A8Is unsubstituted or at least one hydrogen may be optionally substituted by fluorine atoms, methyl or methoxy, or at least one-CH2-is optionally substituted by-O-or at least one-CH-may be substituted by-N-. Z3And Z4Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-. X1And X2Each independently a single bond, an alkyl group of 1 to 6 carbon atoms, wherein X1And X2At least one of-CH2-canOptionally substituted by-O-, -COO-, -OCO-, -CH ═ CH-or-C ≡ C-. Y is1And Y2Each independently is a polymerizable group, wherein the polymerizable group has a structure represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6) or formula (7):
n3is an integer of 0 to 2, and when n3When 2, two A7And two Z4May be the same or different.
For example, the polymerizable compound of formula (IV) may be, but is not limited to, a polymerizable compound having a structure represented by any one of formula (IV-1) and formula (IV-2):
according to the aforementioned liquid crystal composition, the content of the polymerizable compound of formula (IV) may preferably be more than 0 part by weight and less than 5 parts by weight, more preferably may be more than 0 part by weight and less than 2 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
Liquid crystal display element
The liquid crystal display element of the invention comprises the liquid crystal composition. For the liquid crystal composition, please refer to the above, which is not described herein, and the structure and manufacturing method of the liquid crystal display device are conventional and are not described herein.
Method for evaluating liquid crystal compound/liquid crystal composition
The liquid to be tested may be a liquid crystal compound or a liquid crystal composition.
Clearing Point temperature (Tni, deg.C): using a Differential Scanning Calorimeter (DSC) system, placing the liquid to be detected on an aluminum plate, accurately weighing 0.5-10 mg, and determining the phase change temperature according to the starting points of an endothermic peak and an exothermic peak of the liquid to be detected, which appear due to phase change. The phase change is represented by: the crystalline phase is denoted C, the smectic phase is denoted S, the nematic phase is denoted N and the liquid is denoted I. Wherein the phase transition temperature from the nematic phase to the liquid is the clearing point temperature (Tni).
Dielectric anisotropy (Δ): filling the liquid to be detected into a liquid crystal box, applying a voltage of 0V to 20V to the liquid crystal box at the temperature of 25 ℃, wherein the average dielectric constant measured in the direction parallel to the long axis of the liquid crystal molecules is/and the average dielectric constant measured perpendicular to the long axis of the liquid crystal molecules is vertical, and the dielectric anisotropy (delta) is vertical.
Refractive index anisotropy (Δ n): the liquid to be measured was measured using an Abbe refractometer (manufactured by ATAGO; model: DR-M2) having a polarizing plate attached to an eyepiece. Firstly, wiping the surface of a main prism of an Abbe refractometer in a single direction, then dripping a small amount of liquid to be measured on the main prism, and then measuring the refractive index anisotropy by using an optical filter with the wavelength of 589nm at the test temperature of 25 ℃. When the polarization direction is parallel to the wiping direction, the measured refractive index is n/; when the polarization direction is vertical to the wiping direction, the measured refractive index is n ^ T; refractive index anisotropy (Δ n) ═ n | | -n ″.
Preparation of liquid-crystalline compounds
Preparation of liquid Crystal Compound I-1
Step 1 Synthesis of Compound C
To a 250mL two-necked round-bottomed flask, 30mL of methylene Chloride (CH) was sequentially added2Cl2) 1.1g (5.2mmol) of Compound A, 0.81g (5.2mmol) of Compound B and 2g (7.8mmol) of triphenylphosphine. Under ice bath, 1.6g (7.8mmol) of diisopropylazodicarboxylic acid was slowly added, the mixture was stirred at room temperature for 1 hour, completion of the reaction was confirmed by TLC plate (developing solution is ethyl acetate/n-hexane at a volume ratio of 2: 10), after completion of the reaction, concentration was performed under reduced pressure, and finally, 1.1g of white solid, i.e., compound C, was obtained by purification using column chromatography (eluting solution is a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane is 2: 10).
Step 2. Synthesis of I-1
In a 250mL double-necked round-bottomed flask, add sequentially15mL of THF, 0.36g (1mmol) of the compound C, 0.39g (1.5mmol) of the compound D, 3mL of aqueous potassium carbonate (1N concentration) and 0.05g of palladium triphenylphosphine salt [ Pd (PPh)3)4]To form a mixture. The mixture was stirred under reflux for 18 hours, and the completion of the reaction was confirmed by TLC (chromatography liquid was a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane was 1: 10), and after completion of the reaction, 20mL of water was added to stop the reaction. Extracting the reacted mixture with ethyl acetate, repeatedly extracting for three times, collecting an organic layer, removing water with anhydrous magnesium sulfate, filtering, concentrating under reduced pressure, and purifying by using a column chromatography (the flushing extract is a mixed solution of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane is 1: 10) to obtain 0.40g of white solid, namely I-1. GCMS: 484.5724[ M/z ═ M]+。1H-NMR(CDCl3,400MHz),(ppm):0.80-1.36(m,16H),1.821(d,J＝10.4Hz,2H),1.931(d,J＝11.6Hz,2H),2.710(q,J＝7.6Hz,2H),3.88(d,J＝6.4Hz,2H),6.79-6.84(m,1H),7.06-7.09(m,1H),7.10-7.17(m,1H),7.22-7.26(m,1H),7.313(d,J＝8.0Hz,2H),7.510(d,J＝8.0Hz,2H)。
Preparation of liquid Crystal Compound I-2
The synthesis steps are carried out according to the steps and conditions of I-1, except that the compound B is changed into the compound F, the compound D is changed into the compound E, and the amount of the compound D is changed into gram according to the mole number, the other synthesis steps are the same, and finally I-2 is prepared. GCMS: 488.5863[ M/z ═ M]+。
Preparation of liquid Crystal Compound I-5
In a 250mL two-necked round-bottomed flask, 15mL of THF, 0.36g (1mmol) of Compound C, 0.42g (1.5mmol) of Compound E, 3mL of an aqueous potassium carbonate solution (1N in concentration) and 0.05g of palladium triphenylphosphine salt [ Pd (PPh)3)4]To formA mixture of the above. The mixture was stirred under reflux for 18 hours, and the completion of the reaction was confirmed by TLC (chromatography liquid was a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane was 1: 10), and after completion of the reaction, 50mL of water was added to stop the reaction. Extracting the reacted mixture with ethyl acetate, repeatedly extracting for three times, collecting an organic layer, removing water with anhydrous magnesium sulfate, filtering, concentrating under reduced pressure, and purifying by using a column chromatography (the eluting solution is a mixed solution of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane is 1: 10) to obtain 0.42g of white solid, namely I-5. GCMS: 502.6372[ M/z ═ M]+。1H-NMR(CDCl3,400MHz),(ppm):0.83-1.42(m,22H),1.81-1.93(m,6H),2.410(q,J＝7.6Hz,3H),3.862(d,J＝6.4Hz,2H),6.016(s,1H),6.79-6.84(m,1H),7.02-7.04(m,3H)。
Evaluation results of liquid Crystal Compound
The liquid crystal compounds (I-1), (I-2) and (I-5) of the present invention and the liquid crystal compounds (R-1) to (R-2) of the reference examples were dissolved in a mother liquor 1 at a ratio of 10%, and Tni, Δ n and the like were measured. The liquid crystal compounds (I-1), (I-2) and (I-5) and the liquid crystal compound (R-2) of the reference example were placed in the mother liquor 1 and the mother liquor 2, respectively, and the solubility of the liquid crystal compounds was confirmed. The structures of the liquid crystal compounds (R-1) to (R-2) in the reference examples are shown in Table one, the compositions and contents of the mother liquids 1 and 2 are shown in Table two, the solubility results are shown in Table three, and the results of extrapolation calculation after the measurements of Tni, Δ and Δ n are shown in Table four.
As can be seen from the results in Table III, the solubility of the liquid crystal compounds (I-1), (I-2) and (I-5) in the mother liquor 1 or 2 can reach 10%, while the solubility of the reference example (R-2) in the mother liquor 1 or 2 is less than 4%, compared with the better solubility of the liquid crystal compounds (I-1), (I-2) and (I-5) in the mother liquor 1 or 2.
Furthermore, it is clear from the results in Table IV that the liquid crystal compounds (I-1), (I-2) and (I-5) have higher negative dielectric anisotropy, higher clearing point temperature and higher refractive index anisotropy than the liquid crystal compounds (R-1) to (R-2) of the reference examples.
Examples of liquid Crystal compositions
The liquid crystal compositions of examples 1 to 6 were prepared. The ingredients of the liquid crystal compositions of examples 1 to 6 are listed in Table five, and the results of measuring the properties of the liquid crystal compositions of examples 1 to 6 are listed in Table six.
As can be seen from the table five, the liquid crystal compound of the present invention can be used for preparing a negative-type liquid crystal composition, which is beneficial to improving the negative dielectric anisotropy, clearing point temperature and refractive index anisotropy of the liquid crystal composition, and further reducing the driving voltage of the liquid crystal composition. Wherein the clearing point temperature (T) of the liquid crystal composition of the present inventionni) Is 65 ℃ to 120 ℃, a dielectric anisotropy (Delta) is-2 to-8, and a refractive index anisotropy (Delta n) is 0.05 to 0.15.
Although the present invention has been described with reference to the above embodiments, it should be understood that various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the invention.
Claims (14)
1. A liquid crystal compound having a structure according to formula (I):
wherein R is1And R2Each independently is alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, R1And the R is2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-, and-O-is not directly linked to-O-, A1And A2Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), or formula (iii-2):
2. a liquid-crystal compound as claimed in claim 1, wherein in the formula (I), the R is1And the R is2Each independently is an alkyl group having 1 to 5 carbon atoms, R1And the R is2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-and-O-is not directly linked to-O-, A1Is a structure represented by the formula (i), A2Is a structure represented by the formula (ii), the formula (iii-1) or the formula (iii-2).
3. A liquid crystal composition comprising the liquid crystal compound according to claim 1 or 2.
4. A liquid crystal composition according to claim 3, wherein in the formula (I), R is1And the R is2Each independently is an alkyl group having 1 to 5 carbon atoms, R1And the R is2Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-and-O-is not directly linked to-O-, A1Is the structure shown in formula (i), A2Is the structure represented by the formula (ii), the formula (iii-1) or the formula (iii-2).
5. The liquid crystal composition of claim 3, wherein the liquid crystal compound is contained in an amount of more than 0 parts by weight and less than 7 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
6. The liquid crystal composition of claim 3, further comprising a compound represented by formula (II) or formula (III):
wherein R is3、R4、R5And R6Each independently is alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, R3R is a hydrogen atom4R is a hydrogen atom5And the R is6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-is optionally substituted by-O-;
wherein A is3、A4And A5Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1), or formula (vi-2):
wherein Z1And Z2Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-; and
wherein n is1And n2Each independently is 1 or 2, and when n is1When it is 2, the two A3And the two Z1Can be the same or different when n is2When it is 2, the two A5And the two Z2May be the same or different.
7. A liquid crystal composition of claim 6 wherein in the compound of formula (II), the R3And the R is4Each independently is alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, R3And the R is4Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, the compound A3And the A4Each independently is the structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2), and Z is1Is a single bond, n1Is 1.
8. A liquid crystal composition of claim 6 wherein in the compound of formula (III), the R5And the R is6Each independently is alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms or alkenyl with 2 to 10 carbon atoms, R5And the R is6Is unsubstituted or at least one hydrogen may optionally be substituted by halogen atoms, or at least one-CH2-optionally substituted by-O-, the compound A5Is the structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (iv-1), formula (iv-2), formula (v-1), formula (v-2), formula (vi-1) or formula (vi-2), and the Z is2Is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-, the n being2Is 1.
9. The liquid crystal composition of claim 7, wherein the compound of formula (II) is contained in an amount of 25 to 65 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
10. The liquid crystal composition of claim 8, wherein the compound of formula (III) is contained in an amount of 30 to 70 parts by weight, based on 100 parts by weight of the total weight of the liquid crystal composition.
11. The liquid crystal composition of claim 3, further comprising a polymerizable compound.
12. A liquid crystal composition of claim 11 wherein the polymerizable compound has the structure shown in formula (IV):
wherein A is6、A7And A8Each independently is a structure represented by formula (i), formula (ii), formula (iii-1), formula (iii-2), formula (vii), formula (viii), formula (ix), formula (x) or formula (xi):
and the A is6A is the same as7And the A8Is unsubstituted or at least one hydrogen may be optionally substituted by fluorine atoms, methyl or methoxy, or at least one-CH2-optionally substituted by-O-or at least one-CH-may be substituted by-N-;
wherein Z3And Z4Each independently is a single bond, -CH2O-、-CH＝CH-、-CH2CH2-or-C ≡ C-;
wherein X1And X2Each independently a single bond, an alkyl group having 1 to 6 carbon atoms, and X1And the X2At least one of-CH2-optionally substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-;
wherein Y is1And Y2Each independently is a polymerizable group having a structure represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6) or formula (7):
wherein n is3Is an integer of 0 to 2, and when n is3When it is 2, the two A7And the two Z4May be the same or different.
13. A liquid crystal composition as claimed in claim 3, wherein the clearing point temperature (T) of the liquid crystal compositionni) Is 65 ℃ to 120 ℃, a dielectric anisotropy (Delta) is-2 to-8, and a refractive index anisotropy (Delta n) is 0.05 to 0.15.
14. A liquid crystal display element comprising the liquid crystal composition according to any one of claims 3 to 13.
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| CN101827805A (en) * | 2007-09-10 | 2010-09-08 | 智索株式会社 | Liquid crystalline compound, liquid crystal composition, and liquid crystal display element |
| TW201321484A (en) * | 2011-11-28 | 2013-06-01 | Jnc Corp | Liquid crystal composition and usage thereof, and liquid crystal display element and method for manufacturing the same |
| JP2014234357A (en) * | 2013-05-31 | 2014-12-15 | Dic株式会社 | Compound, liquid crystal composition, and display element |
| CN104774621A (en) * | 2014-01-15 | 2015-07-15 | 江苏和成显示科技股份有限公司 | Negative liquid crystal compound and composition comprising same and application thereof |
| KR20180058207A (en) * | 2016-11-23 | 2018-05-31 | 주식회사 동진쎄미켐 | Polymerizable compound and liquid crystal composition comprising the same |
| CN108473870A (en) * | 2015-12-31 | 2018-08-31 | 株式会社东进世美肯 | Liquid crystal composition and liquid crystal display device comprising same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101827805A (en) * | 2007-09-10 | 2010-09-08 | 智索株式会社 | Liquid crystalline compound, liquid crystal composition, and liquid crystal display element |
| TW201321484A (en) * | 2011-11-28 | 2013-06-01 | Jnc Corp | Liquid crystal composition and usage thereof, and liquid crystal display element and method for manufacturing the same |
| JP2014234357A (en) * | 2013-05-31 | 2014-12-15 | Dic株式会社 | Compound, liquid crystal composition, and display element |
| CN104774621A (en) * | 2014-01-15 | 2015-07-15 | 江苏和成显示科技股份有限公司 | Negative liquid crystal compound and composition comprising same and application thereof |
| CN108473870A (en) * | 2015-12-31 | 2018-08-31 | 株式会社东进世美肯 | Liquid crystal composition and liquid crystal display device comprising same |
| KR20180058207A (en) * | 2016-11-23 | 2018-05-31 | 주식회사 동진쎄미켐 | Polymerizable compound and liquid crystal composition comprising the same |
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