CN114231296A - Negative liquid crystal composition and application - Google Patents
Negative liquid crystal composition and application Download PDFInfo
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- CN114231296A CN114231296A CN202111614820.6A CN202111614820A CN114231296A CN 114231296 A CN114231296 A CN 114231296A CN 202111614820 A CN202111614820 A CN 202111614820A CN 114231296 A CN114231296 A CN 114231296A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 119
- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 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 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 10
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- OBKSFBWOZSQGGC-UHFFFAOYSA-N (4-ethoxy-2,3-difluorophenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C(F)=C1F OBKSFBWOZSQGGC-UHFFFAOYSA-N 0.000 description 1
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- AVOGLGBKOFOSBN-UHFFFAOYSA-N 1-ethoxy-2,3-difluorobenzene Chemical compound CCOC1=CC=CC(F)=C1F AVOGLGBKOFOSBN-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000000007 visual effect Effects 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 negative liquid crystal composition and application thereof, belonging to the field of liquid crystal materials. The liquid crystal composition comprises at least one compound with a structure shown in a general formula I,
at least one compound of formula II:
and at least one compound of formula III:
Description
Technical Field
The invention relates to a negative liquid crystal composition and application thereof, in particular to a dielectric negative liquid crystal composition containing a substituted cyclohexyl structure compound and application thereof, belonging to the field of liquid crystal materials.
Background
Liquid crystal display elements using the liquid crystal composition are widely used in displays of watches, calculators, word processors, and the like. These liquid crystal display elements utilize refractive index anisotropy, dielectric anisotropy, and the like of liquid crystal compounds.
These liquid crystal display elements include a liquid crystal composition having appropriate physical properties. General physical properties required for a liquid crystal compound as a component of a liquid crystal composition are as follows:
(1) chemically stable and physically stable;
(2) has a high bright point (liquid crystal phase-isotropic phase transition temperature);
(3) a low lower limit temperature of a liquid crystal phase (optically isotropic liquid crystal phase such as a nematic phase, a cholesteric phase, a smectic phase, and a blue phase, etc.);
(4) excellent compatibility with other liquid crystal compounds;
(5) dielectric anisotropy with appropriate magnitude;
(6) with a suitably sized refractive index anisotropy.
When a liquid crystal composition containing the chemically and physically stable liquid crystal compound according to (1) is used for a liquid crystal display device, the voltage holding ratio can be improved. In addition, if the liquid crystal composition contains the liquid crystal compound having a high clearing point or a low lower limit temperature of the liquid crystal phase as described in (2) and (3), the temperature range of the nematic phase or the optically isotropic liquid crystal phase can be expanded, and the liquid crystal composition can be used as a display element in a wide temperature range. Liquid crystal compounds are generally used as liquid crystal compositions prepared by mixing with many other liquid crystal compounds in order to exhibit properties that are difficult to be exhibited by a single compound. Therefore, the liquid crystal compound used in the liquid crystal display element is preferably excellent in compatibility with other liquid crystal compounds and the like as described in (4). In recent years, liquid crystal display elements having higher display performance, such as contrast, display capacity, response time characteristics, and the like, have been particularly demanded. Further, a liquid crystal composition having a low rotational viscosity and a low driving voltage is required for the liquid crystal material to be used.
Negative liquid crystals, which were proposed at the earliest in the last 80 years, were mainly used for VA mode, which has very excellent contrast properties, but has significant viewing angle problems and response time problems. The sequential proposal of modes such as MVA, PVA, PSVA and the like improves the problems of the display speed and the visual angle of negative liquid crystal, but still needs to develop a high-performance liquid crystal composition to meet the continuously improved requirements of people on liquid crystal displays; on the other hand, the reliability of the liquid crystal display is closely related to the performance of the liquid crystal material, and for the liquid crystal display, because the backlight exists and the backlight irradiation is performed for a long time, the working temperature of the liquid crystal display is increased, the working condition of the liquid crystal is deteriorated, and the unstable liquid crystal composition causes the performance of the liquid crystal display to have the bad phenomena of image retention and the like, so that the liquid crystal composition with proper optical anisotropy, good low-temperature performance and high reliability, especially high-temperature reliability is needed.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a dielectric negative liquid crystal composition, which can improve the low-temperature intersolubility of the liquid crystal composition and reduce the rotational viscosity. Meanwhile, the liquid crystal composition has good high-temperature reliability.
In order to achieve the purpose, the invention adopts the following technical scheme:
a negative liquid crystal composition comprises at least one compound with a structure shown in a general formula I,
at least one compound of formula II:
and at least one compound of formula III:
wherein, in the general formula I, R1、R2Each represents H, or an alkyl or alkoxy group having 1 to 12 carbon atoms, wherein one or more-CH groups2-each independently can be replaced by-O-, -CH ═ CH-, -C ≡ C-, -CO-O-, or-O-CO-in such a way that the oxygen atoms are not directly linked, -CH2-hydrogen on the radical may be substituted by halogen;
ring A represents
Z represents a C-C single bond, -CH2O-or-CH2CH2-；
a represents an integer of 0 to 3.
Further, in the compounds of the formula I, R1、R2Independently represent H, or alkyl or alkoxy of 1-5C, wherein one or more-CH2-each independently can be replaced by-O-, -CH ═ CH-, -C ≡ C-, -CO-O-, or-O-CO-in such a way that the oxygen atoms are not directly linked, -CH2-hydrogen on the radical may be substituted by halogen; z represents a single bond, -CH2O-or-CH2CH2-; n represents 0 or 1.
In the formulae II and III, the rings B1, B2, C1 and C2 each independently of one another
RB1、RB2、RC1、RC2Each independently of the other represents an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 12 carbon atoms, or an alkenyl group of 2 to 12 carbon atoms;
LB1、LB2、LC1、LC2each independently of the other represents F, Cl, CH3Or CF3；
ZBrepresents-CH2CH2-、-CH＝CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-C2F4-, or-CF ═ CF-;
b represents 0, 1 or 2; c represents 0, 1 or 2.
Preferably, the compound of formula I may be selected from one or more of the following compounds of formula I:
wherein R is1、R2Each represents H, or an alkyl or alkoxy group having 1 to 12 carbon atoms, wherein one or more-CH groups2-each independently can be replaced by-O-, -CH ═ CH-, -C ≡ C-, -CO-O-, or-O-CO-in such a way that the oxygen atoms are not directly linked, -CH2The hydrogen of the radical may be replaced by halogen.
More preferably, the compound of formula I may be selected from one or more of the following group of compounds:
in the liquid crystal composition of the present invention, the mass content of the compound represented by the general formula I is 0.01 to 60%, preferably 0.01 to 50%, and more preferably 0.01 to 40%.
In some embodiments of the present invention, the compound represented by formula II preferably accounts for 1-60%, more preferably 5-50% of the total weight of the negative liquid crystal composition.
In some embodiments of the present invention, it is preferred that the compound represented by the general formula II is selected from one or more of the group consisting of the following compounds II-1 to II-58:
in some embodiments of the present invention, the compound represented by formula III preferably accounts for 1 to 60%, and more preferably 5 to 50% of the total weight of the negative liquid crystal composition.
In some embodiments of the present invention, it is preferred that the compound represented by the general formula III is selected from one or more of the following compounds III-1 to III-60:
in some embodiments of the invention, one or more compounds of formula IV are also included:
wherein rings D1, D2, D3 each independently represent
RD1、RD2Each independently of the other represents an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 12 carbon atoms, or an alkenyl group of 2 to 12 carbon atoms;
d represents 0 or 1.
The compound shown in the general formula IV accounts for 1-60% of the total weight of the negative liquid crystal composition, preferably 1-50%, and more preferably 5-50%.
In some embodiments of the present invention, it is preferred that the compound represented by formula IV is selected from one or more compounds selected from the group consisting of the following compounds IV-1 to IV-85:
in some embodiments of the invention, one or more compounds having a structure according to formula V may also be added:
wherein R isE1And RE2The same or different, each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms;
rings E1, E2, E3, E4 each independently of the others
One or more H on the phenyl ring may be substituted by F.
In some embodiments of the present invention, the compound of formula V comprises from 0 to 10%, more preferably from 0 to 8% or from 0.01 to 10%, more preferably from 0.1 to 6% by weight of the total weight of the negative liquid crystal composition.
The compound represented by the general formula V is one or more compounds selected from the group consisting of the following compounds V-1 to V-68:
in addition to one or more compounds shown in general formulas I, II and III, the negative liquid crystal composition also comprises one or more polymerizable liquid crystal compounds shown in general formula VI, wherein the structure of the general formula VI is as follows:
in the general formula VI, R3、R4Each independently represents an acrylate or methacrylate; l is51、L52、L53、L54、L55、L56Each independently represents H, F, methyl or methoxy; d represents 0 or 1.
Preferably, the compound of formula VI is selected from one or more of the following compounds of formulae VI-1 to VI-10:
in the liquid crystal composition, the amount of the polymerizable compound shown in the general formula VI is 0.1-3% of the total weight of the liquid crystal composition, and preferably 0.2-0.5% of the total weight of other liquid crystal compounds in the liquid crystal composition.
In another aspect, the present invention provides a liquid crystal composition having negative dielectric anisotropy, further comprising one or more additives, such as stabilizers, etc., known to those skilled in the art and described in the literature.
For example, one or more of the following stabilizers may be added to the liquid crystal mixture of the present invention:
preferably, the stabilizer is selected from one or more of the following structural stabilizers:
in the stabilizer, n represents an integer of 1 to 8.
In the embodiment of the present invention, it is preferable that the stabilizer accounts for 0 to 5% by weight of the total weight of the liquid crystal composition; more preferably, the stabilizer is 0-1% of the total weight of the liquid crystal composition; as a particularly preferred scheme, the stabilizing agent accounts for 0.01-0.2% of the total weight of the liquid crystal composition.
The negative liquid crystal composition is applied to the preparation of liquid crystal display devices, and the liquid crystal display devices comprise VA, MVA, PVA, PSVA, IPS and FFS mode liquid crystal display devices. The liquid crystal composition of the present invention is applicable to liquid crystal display devices, preferably VA-based liquid crystal display devices such as VA, MVA, PVA, and PSVA, and/or IPS-mode and FFS-mode liquid crystal display devices, more preferably MVA, PVA, and PSVA-mode liquid crystal displays, and even more preferably PSVA-mode liquid crystal displays.
The invention has the advantages that:
the compound adopted by the invention has stable chemical and physical properties, good low-temperature intersolubility, low rotational viscosity, large elastic constant, moderate dielectric anisotropy and refractive index anisotropy, and wide applicability.
The negative liquid crystal composition has good low-temperature intersolubility, large elastic constant, short response time and good high-temperature reliability.
Detailed Description
For convenience of expression, in the following examples, the group structures of the liquid crystal compositions are represented by the codes listed in Table 1.
TABLE 1 radical structural code of liquid crystal compounds
The following compounds are exemplified:
the code in Table 1 shows that 3CWO4, 3 represents cyclohexyl, C represents cyclohexane, W represents 2, 3-difluorobenzene, and 4 represents butyl.
The following steps are repeated:
the code in Table 1 indicates M-1CCWO2, wherein M represents meta-substitution, and 1 represents methyl.
The abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.): clearing point (nematic-isotropic phase transition temperature);
Δ n: refractive index anisotropy (589nm, 25 ℃);
Δ ε: dielectric anisotropy (1KHz, 25 ℃);
γ1: represents the rotational viscosity [ mPas ] measured at 25 DEG C]；
Wherein, Delta Epsilon ═ Epsilon||-ε⊥Wherein, epsilon||Is the dielectric constant parallel to the molecular axis,. epsilon. is the dielectric constant perpendicular to the molecular axis, test conditions: 25 ℃ and 1 KHz;
k11: a splay elastic constant;
k33: a bending elastic constant;
VHR voltage holding ratio, measured by TOYO LCM-2 at 5V, 6Hz and 60 ℃.
Example 1: synthesis of Compound M-1CCWO2
The preparation process comprises the following steps:
(1) synthesis of M-1CC (V) WO2
31.6g of 2, 3-difluorophenetole and 300ml of tetrahydrofuran are added into a reaction flask, stirred and cooled to-80 ℃ under the protection of nitrogen. Slowly dropping 90ml of 2.5M butyl lithium solution, and controlling the temperature between-70 ℃ and-75 ℃ in the dropping process. After the butyl lithium is added, the temperature is kept between minus 65 ℃ and minus 75 ℃ under the protection of nitrogen, and the mixture is stirred for 6 hours.
Dissolving 38.8g M-1CCK in 100ml tetrahydrofuran, and dropping at-75-80 deg.c. The temperature is controlled between minus 70 ℃ and minus 75 ℃ and the mixture is stirred for 3 hours. To a 1000ml beaker was added 45ml of concentrated hydrochloric acid, 150ml of water. The reaction solution was slowly poured into the beaker with stirring, and stirred for 30 min. 150ml of toluene was added for extraction. Extracting the water layer with 75ml × 3 toluene for 3 times; the extracted oil layers were combined and washed 2 times with 150ml × 2 crude brine and 1 time with 150ml deionized water.
And adding 0.1g of 2, 6-di-tert-butyl-p-cresol and 4g of p-toluenesulfonic acid into the oil layer for dehydration, starting timing reflux dehydration for 3 hours when the temperature rises to 105 ℃, and continuously removing water. The temperature is reduced to 40 ℃, 150ml of tap water is added for washing once for liquid separation, and then 150ml of 5% sodium bicarbonate aqueous solution is used for washing once. The organic layer is distilled under reduced pressure to obtain a crude product, the crude product is weighed and then recrystallized by ethanol and petroleum ether, filtered and dried to obtain 29.8g of a product. Molecular formula C21H28F2O2，GC-MS:334.2，GC：99％。
(2) Synthesis of M-1CCWO2
50g M-1CC (V) WO2, 300ml toluene, 300ml absolute ethyl alcohol, 10g (wet weight) catalyst 5% Pd-C catalyst are added into a 500ml autoclave, after the addition is finished, nitrogen is used for emptying 6 times, then hydrogen is used for flushing 6 times, the hydrogen pressure is kept under 0.3Mpa for stirring reaction for 2 hours, after the hydrogenation is finished, the hydrogen in the autoclave is replaced by nitrogen for 6 times, the catalyst is removed by filtration, and the filtrate is decompressed and distilled to remove the solvent, thus obtaining a crude product. Adding 3 times of ethanol into the crude product for recrystallization once, and then recrystallizing with ethanol and petroleum ether once to obtain a product 47g M-1CCWO 2. GC: 99%, molecular formula: c21H30F2O2。
The obtained product is analyzed by nuclear magnetic resonance hydrogen spectrum, and the result is as follows:1H NMR(300MHz,CDCl3)δ7.22–7.01(m,1H),6.75(dd,J＝9.4,5.0Hz,1H),4.14(q,J＝6.3Hz,2H),3.13–2.85(m,1H),1.93–1.64(m,7H),1.61–1.11(m,19H),0.89(d,J＝6.0Hz,3H)。
example 2: synthesis of Compound M-1CPWO2
The specific synthetic steps are as follows
(1) Synthesis of M-1C (V) P-Br
Adding 37.7g of p-dibromobenzene into 300ml of THF (tetrahydrofuran), cooling to-70 ℃, dropwise adding 100ml of 2.5M butyl lithium solution, continuously stirring at-70 ℃ for 1h after the addition is finished, dropwise adding 22.4g of M-1CK 30ml of THF solution, and controlling the temperature between-70 ℃ and-65 ℃ during dropwise adding. Then slowly heating to 0 deg.C, slowly pouring into 1000ml of water, extracting with 400ml of toluene, washing organic layer with dilute hydrochloric acid, washing with sodium bicarbonate aqueous solution, washing with water, and drying. Adding 0.4g of P-toluenesulfonic acid into the obtained solution, heating, refluxing, carrying out water separation reaction for 4 hours, cooling to room temperature, adding 200ml of water and 100ml of toluene, extracting, layering, and carrying out post-treatment to obtain an oily substance 35g M-1C (V) P-Br. Molecular formula C13H15Br，GC-MS：250.0。
(2)M-1C(V)PWO2
50g M-1C (V) P-Br, 48g 2, 3-difluoro-4-ethoxyphenylboronic acid, catalyst Pd (PPh) were added into a 1L reaction flask2Cl21.35g of isopropanol and 500ml of isopropanol are heated to reflux reaction for 4 hours under the protection of nitrogen, cooled to room temperature, and added with 200ml of water and 200ml of toluene. The layers were separated, the organic layer was washed with water, dried and concentrated to give crude product, which was recrystallized from ethanol petroleum ether to give 53g of product M-1C (V) PWO2, GC 98%.
(3) Synthesis of M-1CPWO2
66g M-1C (V) PWO2, 300ml toluene, 60ml absolute ethyl alcohol and 10g 5% Pd-C catalyst are added into a 500ml autoclave, after the addition is finished, nitrogen is used for emptying for 6 times, then hydrogen is used for flushing and discharging the nitrogen for 6 times, the hydrogen pressure is kept under 0.3Mpa, stirring and reaction are carried out for 2 hours, after the hydrogenation is finished, the hydrogen in the autoclave is replaced for 6 times by the nitrogen, the catalyst is removed by filtration, and the solvent is removed by reduced pressure distillation of filtrate, thus obtaining a crude product. The crude product was recrystallized once from 3 times ethanol and then once from ethanol + petroleum ether to give 52g of product M-1C (V) PWO 2. GC:99%, molecular formula: c21H24F2O，GC-MS 330.2。
The obtained product is analyzed by nuclear magnetic resonance hydrogen spectrum, and the result is as follows:1H NMR(300MHz,CDCl3)δ7.52(dd,J＝9.3,4.9Hz,1H),7.38–7.15(m,4H),6.96(dd,J＝9.3,4.9Hz,1H),4.14(q,J＝6.2Hz,2H),3.11–2.60(m,1H),2.04–1.29(m,12H),0.93(d,J＝6.2Hz,3H)。
comparative example 1: a mixture LCM-D1 was prepared according to the compounds and weight percentages listed in Table 2 and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in Table 2.
TABLE 2 composition (wt%) and test properties of comparative example 1 liquid crystal composition
| Components | Percentage of | Performance of | |
| 2CPWO2 | 6 | Cp | 75.0 |
| 3CPWO2 | 6 | Δn | 0.098 |
| 3CWO2 | 20 | Δε | -3.0 |
| 3CCWO2 | 10 | γ1 | 80 |
| 3CCWO3 | 8 | K11 | 14.9 |
| 4CCWO2 | 5 | K33 | 15.8 |
| 5CCWO2 | 9 | Low temperature of-20 deg.C | Crystallization for 7 days |
| 5CPO2 | 10 | ||
| 3CC2 | 10 | ||
| 4CC3 | 5 | ||
| 5CC2 | 8 | ||
| 3CPP2 | 3 | ||
| Total of | 100 |
Application example 1
The mixture LCM-1 is prepared according to the proportion of each compound component in the table 3, and is filled between two substrates of a liquid crystal device for performance test, and the test data are shown in the table 3.
Table 3 composition (wt%) and test properties of the liquid crystal composition of application example 1
Application example 2
The mixture LCM-2 is prepared according to the proportion of each compound component in the table 4, and is filled between two substrates of the liquid crystal display for performance test, and the test data are shown in the table 4.
Table 4 composition (wt%) and test properties of liquid crystal composition of application example 2
| Components | Percentage of | Performance of | |
| M1-CPWO2 | 7 | Cp | 75.0 |
| 3CPWO2 | 8 | Δn | 0.099 |
| M-1CWO4 | 15 | Δε | -3.1 |
| 3CCWO2 | 8 | γ1 | 79 |
| M1-CCWO3 | 6 | K11 | 15.1 |
| 4CCWO2 | 5 | K33 | 16.0 |
| 5CCWO2 | 9 | Low temperature of-20 deg.C | Does not crystallize in 10 days |
| 3CPO2 | 11 | ||
| 3CC2 | 10 | ||
| 4CC3 | 10 | ||
| 5CC2 | 8 | ||
| 3CPP2 | 3 | ||
| Total of | 100 |
Application example 3
The mixture LCM-3 is filled between two substrates of the liquid crystal display for performance test, and the test data are shown in Table 5.
TABLE 5 composition (wt%) and test Properties of liquid crystal composition of application example 3
Application example 4
(1) The liquid crystal composition LCM-1 shown in application example 1 and the liquid crystal composite toy LCMD1 of comparative example 1 were mixed with polymerizable monomers represented by formula VI in the following ratio to obtain PSVA mixture, PA-1, PA-2, PA-3 and PA-D1.
TABLE 6 composition of liquid crystal composition of application example 4 (wt%)
| LCM-1 | VI-1 | VI-2 | VI-7 | LCM-D1 | |
| PA-1 | 100 | 0.3 | |||
| PA-2 | 100 | 0.30 | |||
| PA-3 | 100 | 0.30 | |||
| PA-D1 | 0.3 | 100 |
(2) The prepared PSVA mixtures PA-1, PA-2 and PA-3 and LCM-D1 and LCM-1 are respectively filled into a standard VA test box and UV (313nm 5 mw/cm)2) The pretilt angle, threshold voltage and response time were measured separately by irradiating for two minutes at a voltage of 16V, and the results are shown in table 7.
TABLE 7 test Properties of liquid Crystal compositions
| Pretilt angle (°) | Threshold voltage (V) | Response time (ms) | |
| PA-D1 | 87.5 | 2.902 | 12.6 |
| PA-1 | 87.7 | 2.712 | 11.2 |
| PA-2 | 87.0 | 2.685 | 10.6 |
| PA-3 | 87.2 | 2.693 | 10.9 |
(3) The cells were tested for initial Voltage Holding Ratio (VHR) respectively, then baked at 90 ℃ and tested for voltage holding ratio every 100h, and the data are shown in Table 8.
TABLE 8 results of Voltage holding ratio test of liquid crystal composition
| VHR | Initial | 100h | 200h | 300h |
| PA-D1 | 92.47 | 91.47 | 89.90 | 88.36 |
| PA-1 | 93.55 | 93.20 | 92.43 | 91.53 |
| PA-2 | 93.62 | 93.29 | 92.68 | 92.22 |
| PA-3 | 94.09 | 92.56 | 92.17 | 92.05 |
From the above embodiments, it can be seen that the liquid crystal composition provided by the present invention has low viscosity, suitable optical anisotropy, and good low temperature intersolubility, and can reduce the response time of the liquid crystal display, thereby solving the problem of slow response speed of the liquid crystal display, and meanwhile, the liquid crystal composition of the present invention has high temperature reliability. Therefore, the liquid crystal composition provided by the invention is suitable for VA display modes such as VA/MVA/PVA/PSVA and the like and IPS and FFS type TFT liquid crystal display devices; particularly, it is suitable for liquid crystal display devices such as MVA, PVA and PSVA.
Claims (9)
1. A negative liquid crystal composition, characterized by: comprises at least one compound with a structure shown in a general formula I,
at least one compound of formula II:
and at least one compound of formula III:
wherein R is1、R2Each represents H, or an alkyl or alkoxy group having 1 to 12 carbon atoms, wherein one or more-CH groups2-each independently can be replaced by-O-, -CH ═ CH-, -C ≡ C-, -CO-O-, or-O-CO-in such a way that the oxygen atoms are not directly linked, -CH2-hydrogen on the radical may be substituted by halogen;
RB1、RB2、RC1、RC2each independently of the other represents an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 12 carbon atoms, or an alkenyl group of 2 to 12 carbon atoms;
ring A represents
Rings B1, B2, C1 and C2 each independently of the others
LB1、LB2、LC1、LC2Each independently of the other represents F、Cl、CH3Or CF3；
Z represents a C-C single bond, -CH2O-or-CH2CH2-；
ZBrepresents-CH2CH2-、-CH＝CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-C2F4-, or-CF ═ CF-;
a represents an integer of 0 to 3; b represents 0, 1 or 2; c represents 0, 1 or 2.
2. The negative liquid crystal composition according to claim 1, wherein: the compound shown in the general formula I is selected from one or more of the following compounds shown in the general formula:
3. the negative liquid crystal composition according to claim 2, wherein: the compound shown in the general formula I is selected from one or more of the following compounds:
4. the negative liquid crystal composition according to any one of claims 1 to 3, wherein: the negative liquid crystal composition further comprises one or more compounds shown in a general formula IV:
wherein rings D1, D2, D3 each independently represent
RD1、RD2Each independently of the other represents an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 12 carbon atoms, or an alkenyl group of 2 to 12 carbon atoms;
d represents 0 or 1.
5. The negative liquid crystal composition according to claim 4, wherein: the negative liquid crystal composition also comprises one or more compounds with the structure shown in the general formula V:
wherein R isE1And RE2Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms;
rings E1, E2, E3, E4 each independently of the others
One or more H on the phenyl ring may be substituted by F.
6. The negative liquid crystal composition according to claim 5, wherein: further comprises one or more polymerizable liquid crystal compounds shown in a general formula VI, wherein the general formula VI has the structure:
wherein R is3、R4Each independently represents an acrylate or methacrylate; l is51、L52、L53、L54、L55、L56Each independently represents H, F, methyl or methoxy; d represents 0 or 1.
7. The negative liquid crystal composition according to claim 6, wherein: one or more stabilizers are also added into the liquid crystal mixture.
8. The negative liquid crystal composition according to claim 7, wherein: in the liquid crystal composition, the content of the compound shown in the general formula I is 0.01-60%, the content of the compound shown in the general formula II is 1-60%, the content of the compound shown in the general formula III is 1-60%, the content of the compound shown in the general formula IV is 1-60%, the content of the compound shown in the general formula V is 0-10%, the content of the compound shown in the general formula VI is 0.1-3%, and the content of the stabilizer is 0-5% by mass percentage.
9. Use of the negative liquid crystal composition according to any one of claims 1 to 8 for the preparation of liquid crystal display devices including VA, MVA, PVA, PSVA, IPS and FFS mode liquid crystal display devices.
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| CN109796991A (en) * | 2017-11-16 | 2019-05-24 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl |
| TW201920620A (en) * | 2017-07-25 | 2019-06-01 | 日商迪愛生股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN112143508A (en) * | 2020-10-09 | 2020-12-29 | 烟台显华化工科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device |
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| CN108728115A (en) * | 2017-04-20 | 2018-11-02 | 北京八亿时空液晶科技股份有限公司 | A kind of negative dielectric nematic phase liquid crystal composition and its application |
| TW201920620A (en) * | 2017-07-25 | 2019-06-01 | 日商迪愛生股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN109796991A (en) * | 2017-11-16 | 2019-05-24 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl |
| CN112143508A (en) * | 2020-10-09 | 2020-12-29 | 烟台显华化工科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device |
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