CN104016830B - A kind of cyclohexanes liquid-crystal compounds and liquid-crystal composition - Google Patents
A kind of cyclohexanes liquid-crystal compounds and liquid-crystal composition Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 265
- 239000000203 mixture Substances 0.000 title claims abstract description 119
- 150000001875 compounds Chemical class 0.000 title claims abstract description 109
- 150000001934 cyclohexanes Chemical class 0.000 title abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 34
- -1 butoxymethyl Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 37
- 238000002360 preparation method Methods 0.000 abstract description 18
- 239000000178 monomer Substances 0.000 abstract description 9
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 8
- 230000000007 visual effect Effects 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000005303 weighing Methods 0.000 description 11
- 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 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000012071 phase Substances 0.000 description 7
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical group CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000013213 extrapolation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GAZGXIDBUIKYDM-UHFFFAOYSA-N (4-ethyl-2,3-difluorophenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C(F)=C1F GAZGXIDBUIKYDM-UHFFFAOYSA-N 0.000 description 1
- NUPWGLKBGVNSJX-UHFFFAOYSA-N 1-bromo-4-propylbenzene Chemical compound CCCC1=CC=C(Br)C=C1 NUPWGLKBGVNSJX-UHFFFAOYSA-N 0.000 description 1
- KZCKOVSBURQMDH-UHFFFAOYSA-N 1-bromo-4-propylcyclohexane Chemical compound CCCC1CCC(Br)CC1 KZCKOVSBURQMDH-UHFFFAOYSA-N 0.000 description 1
- 239000005264 High molar mass liquid crystal Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
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- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 238000011911 α-alkylation Methods 0.000 description 1
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- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of cyclohexanes liquid-crystal compounds, this liquid-crystal compounds has the structure shown in formula I.This liquid-crystal compounds is applied in nematic liquid crystal composition, it is possible to well dissolve each other with other liquid crystal monomers, and effectively reduces the rotary viscosity of liquid-crystal composition, significantly improves the response time of liquid-crystal composition, reaches the purpose of quickly response.The invention also discloses a kind of positive dielectric anisotropy liquid crystal composition comprising formula I liquid-crystal compounds and a kind of negative dielectric anisotropy liquid crystal composition comprising formula I liquid-crystal compounds, both liquid-crystal compositions are respectively provided with response speed quickly and very short response time, preparation suitable in plurality of display modes liquid crystal display and liquid crystal display cells, good visual experience can be brought to beholder, have broad application prospects and market value.
Description
Technical Field
The invention relates to a cyclohexane liquid crystal compound for improving the response speed of liquid crystal and a liquid crystal composition containing the cyclohexane liquid crystal compound, belonging to the technical field of liquid crystal display.
Background
Liquid crystals are widely used in light and thin display technologies since the middle of the 20 th century because of their special physical, chemical and optical properties. Many liquid crystal display elements have been produced by utilizing the characteristics (optical anisotropy Δ n, dielectric anisotropy Δ) of liquid crystal compounds, and have been used in the fields of clocks, calculators, measuring instruments, automobile panels, word processors, electronic organizers, mobile phones, printers, computers, TVs, and the like. The liquid crystal compounds used in the liquid crystal display devices have liquid crystal phases inherent therein, and the phase morphology thereof is roughly classified into three types, i.e., a nematic phase, a smectic phase, and a cholesteric phase. Among them, nematic liquid crystals are most widely used.
The liquid crystal driving method used in the liquid crystal display device mainly includes a static driving method, a multiplex driving method, an active matrix driving method, a dual-frequency driving method, and the like. Among display systems used in liquid crystal display devices, Dynamic Scattering (DS), guest-host (GH), Twisted Nematic (TN), Super Twisted Nematic (STN), Thin Film Transistor (TFT), and Ferroelectric Liquid Crystal (FLC) have been developed; in recent years, 3 types of TN type, STN type, and TFT type have become mainstream in the market and development.
Liquid crystal materials for display use are required to satisfy ① good chemical, physical and thermal stability, stability against electric field and electromagnetic radiation, ② rotational viscosity (. gamma.)1) Low dielectric anisotropy △ and optical anisotropy △ n which are ③ suitable, good compatibility of ④ and other liquid crystal compounds, and a wide nematic phase temperature range ⑤, in order to meet the performance requirements, liquid crystals with low rotational viscosity and low threshold voltage need to be used, however, no single liquid crystal compound which can meet the performance requirements has been found so far, and the performance requirements of liquid crystal display materials can be met only by mixing a few or even dozens of liquid crystal compounds into a liquid crystal composition, and the requirements on the response speed of the liquid crystal composition are gradually increased due to the continuous emergence of display elements such as high definition TV and 3D display in recent years.
The rigid skeleton of the early-stage polymer liquid crystal with a liquid crystal phase structure usually contains a benzene ring structure, and the benzene ring structure contains a large conjugated system which has strong absorption to ultraviolet light, so that the stability of the material is influenced; along with the research, cyclohexane rings are more and more introduced into a rigid framework, when benzene rings in liquid crystals are replaced by the cyclohexane rings, a pi electron system is reduced or disappears, the charge density distribution is reduced, the polarization is weakened, and the cyclohexane rings are mutually overlapped in a staggered mode to form close packing, so that the clearing point of the liquid crystals is increased.
Conventionally, a number of proposals have been made on nematic liquid crystal compositions having excellent responsiveness using cyclohexane compounds. Japanese patent laid-open No. 6-56717 provides a nematic liquid crystal composition excellent in responsiveness, which can form a large pretilt angle and is large and the incidence of stripe alignment defects is significantly reduced, which is chemically stable, can be driven at a low voltage, and can respond to high-time divisional driving; japanese patent laid-open No. Hei 7-126205 provides a nematic liquid crystal composition having a suitable complex refractive index, a wide drivable temperature range, excellent response and a good contrast, and also provides a novel cyclohexane compound for use in liquid crystal display devices such as TN-LCD, STN-LCD and TFT-LCD having improved electro-optical characteristics, which composition has improved response speed from a reverse ferroelectric state to a ferroelectric state. Japanese patent application No. 2010-162348 relates to a material for a liquid crystal display element which contains a liquid crystal compound having a cyclohexane ring, and which can effectively reduce the threshold voltage without increasing the viscosity when mixed with a liquid crystal composition which has been widely used conventionally. However, the response speed of the liquid crystal compositions disclosed so far is still slow, and the display requirements of liquid crystal display elements cannot be fully satisfied.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a cyclohexane liquid crystal compound for reducing the response time of nematic liquid crystal and a nematic liquid crystal composition which contains the liquid crystal compound and has fast response speed.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a cyclohexane liquid crystal compound has a structure shown in a formula I,
in the formula I, the compound has the following structure,
R11、R12respectively is any one of the following groups ① - ④:
a C1-9 alkyl group,
(ii) a group represented by (i) wherein any single bond is replaced by an unsaturated bond,
③ any-CH2A group represented by ①, ② substituted by-O-, -CO-or-COO-,
(iv) a group represented by (i), (ii), or (iii) wherein any hydrogen atom is substituted with a halogen atom or-CN;
Z11、Z12is any one group of single bond, -OCO-or-OOC-respectively;
X1～X8、Y1～Y8are each a hydrogen atom or a halogen atom, and at least one halogen atom is contained therein; when X is present2And/or Y2When it is a halogen atom, X1、X3～X8、Y1、Y3～Y8Not simultaneously hydrogen atoms.
The positive dielectric anisotropy liquid crystal composition of the cyclohexane liquid crystal compound comprises, by mass, 2-40 parts of a first component, 30-90 parts of a second component, 0-80 parts of a third component and 0-20 parts of a fourth component; the first component is a cyclohexane liquid crystal compound shown as a formula I, the second component is at least one of liquid crystal compounds shown as a formula II, a formula III and a formula IV, the third component is a liquid crystal compound shown as a formula V, and the fourth component is a liquid crystal compound shown as a formula VI;
in the formula,
R2、R3、R4、R5each is an alkyl group having 1 to 9 carbon atoms;
R61、R62each of which is any one of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which is optionally substituted by-F, and an alkenyl group having 2 to 12 carbon atoms, which is optionally substituted by-F;
M2、M3、M41、M42are each-H or-F, M5is-F or-OCF3；
Z6Is a single bond or-CH2CH2-。
A negative dielectric anisotropy liquid crystal composition containing the cyclohexane liquid crystal compound comprises 2-40 parts by mass of a component A, 30-90 parts by mass of a component B and 0-20 parts by mass of a component C; the component A is a cyclohexane liquid crystal compound shown as a formula I, the component B is a liquid crystal compound shown as a formula VII, and the component C is a liquid crystal compound shown as a formula VI and/or a formula VIII;
in the formula,
R61、R62、R71、R72、R81、R82each of which is any one of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which is optionally substituted by-F, and an alkenyl group having 2 to 12 carbon atoms, which is optionally substituted by-F;
Z6is a single bond or-CH2CH2-；Z7、Z8Are each a single bond, -CH2CH2-、-CH2Any one of O-or-COO-;
M71、M72are respectively-F or-Cl;
n is any one of 1, 2 or 3;
the ring A and the ring B are respectively a single bond,Any one of the above;
ring C and ring D are eachAny one of the above; however, when n =1, ring D can only be
Due to the adoption of the technical scheme, the technical progress of the invention is as follows:
the invention provides a novel cyclohexane liquid crystal compound. The liquid crystal compound takes dicyclohexyl as a basic structure, and a halogen atom is introduced at the side position of cyclohexane, and a proper group is introduced at the end position of the cyclohexane, so that the liquid crystal compound with proper dielectric anisotropy (delta) and good optical anisotropy (delta n) is obtained. The cyclohexane liquid crystal compound is applied to the nematic liquid crystal composition, can be well dissolved with other liquid crystal monomers, effectively reduces the rotational viscosity of the liquid crystal composition, remarkably improves the response time of the liquid crystal composition, and achieves the purpose of quick response.
The invention also discloses a positive dielectric anisotropy liquid crystal composition containing the cyclohexane liquid crystal compound. The liquid crystal composition has excellent performance, moderate birefringence, proper high positive dielectric anisotropy, very low rotary viscosity and fast response speed, is suitable for the preparation of liquid crystal displays and liquid crystal display elements in various display modes, is particularly suitable for a high-end IPS display mode, can bring good visual experience to a viewer, and has wide application prospect and market value.
The invention also discloses a negative dielectric anisotropy liquid crystal composition containing the cyclohexane liquid crystal compound. The liquid crystal composition has excellent performance, high response speed, short response time, moderate birefringence, properly high negative dielectric anisotropy and low rotational viscosity, is suitable for the preparation of liquid crystal displays and liquid crystal display elements in various display modes, is particularly suitable for a high-end VA display mode, can bring good visual experience to a viewer, and has wide application prospect and market value.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Except for special description, the dosage units of the components related in the specification are parts by mass; the temperature unit is centigrade (DEG C), and the concrete meanings and test conditions of other symbols are as follows:
m/z: mass to charge ratio, detected by mass spectrometry.
Δ n: optical anisotropy, Δ n = ne-no；noRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
the method for testing the delta n of the liquid crystal composition comprises the following steps: adding 10% of a liquid crystal composition to be tested into a mother liquid crystal as a sample for testing, and calculating an extrapolation value by an extrapolation method according to a test value of the obtained sample, wherein the extrapolation value is delta n of the liquid crystal composition to be tested; the extrapolated value is calculated as: extrapolated value = [100 × (test of specimen)
Value) - (weight percent of parent liquid crystal) × (test value of parent liquid crystal) ]/weight percent of compound.
The parent liquid crystal is:
a cyclohexane liquid crystal compound has a structure shown in a formula I:
in the formula I, the compound has the following structure,
R11、R12respectively is any one of the following groups ① - ④:
a C1-9 alkyl group,
(ii) a group represented by (i) wherein any single bond is replaced by an unsaturated bond,
③ any-CH2①, ② substituted by-O-, -CO-or-COO-The radical(s) is (are),
(iv) a group represented by (i), (ii), or (iii) wherein any hydrogen atom is substituted with a halogen atom or-CN;
R11、R12preferably any group selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, vinyl, allyl, butenyl, ethynyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl, perfluoromethyl, perfluoroethyl, perfluoropropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, perfluorovinyl, perfluoroallyl, isopropyl, 1-methylpropyl, 2-butylmethyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 1-methylpentyl;
Z11、Z12is any one group of single bond, -OCO-or-OOC-respectively;
X1～X8、Y1～Y8are each a hydrogen atom or a halogen atom, and at least one halogen atom is contained therein; when X is present2And/or Y2When it is a halogen atom, X1、X3～X8、Y1、Y3～Y8Not simultaneously hydrogen atoms.
The cyclohexane liquid crystal compound is preferably selected from liquid crystal compounds shown in formulas I-1 to I-6:
the liquid crystal compound represented by the formula I-1 is preferably a liquid crystal compound represented by the formula I-1-1 to formula I-1-5:
the preparation method of the liquid crystal compound shown in the formula I-1 comprises the following steps:
wherein, the step A is SUZUKI coupling reaction, and the step B is catalytic hydrogenation reaction.
The liquid crystal compounds shown in the formulas I-2 to I-5 can be prepared by selecting corresponding raw materials according to the method.
The liquid crystal compound represented by the formula I-6 is preferably a liquid crystal compound represented by the formulae I-6-1 to I-6-4:
the preparation method of the liquid crystal compound shown in the formula I-6 comprises the following steps:
wherein, step a is an alpha-alkylation reaction; and step b is fluorination reaction, and the adopted fluorinating agent is diethylaminosulfur trifluoride (DAST).
A positive dielectric anisotropy liquid crystal composition comprises, by mass, 2-40 parts of a first component, 30-90 parts of a second component, 0-80 parts of a third component and 0-20 parts of a fourth component; the first component is a cyclohexane liquid crystal compound shown as a formula I, the second component is at least one of liquid crystal compounds shown as a formula II, a formula III and a formula IV, the third component is a liquid crystal compound shown as a formula V, and the fourth component is a liquid crystal compound shown as a formula VI;
in the formula,
R2、R3、R4、R5each is an alkyl group having 1 to 9 carbon atoms;
R61、R62each of which is any one of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which is optionally substituted by-F, and an alkenyl group having 2 to 12 carbon atoms, which is optionally substituted by-F;
M2、M3、M41、M42are each-H or-F, M5is-F or-OCF3；
Z6Is a single bond or-CH2CH2-。
The positive dielectric anisotropy liquid crystal composition preferably comprises 5-30 parts by mass of a first component, 45-80 parts by mass of a second component, 20-60 parts by mass of a third component and 0-15 parts by mass of a fourth component; most preferably 8 to 15 parts of the first component, 55 to 65 parts of the second component, 20 to 30 parts of the third component and 4 to 6 parts of the fourth component.
A negative dielectric anisotropy liquid crystal composition comprises 2-40 parts by mass of a component A, 30-90 parts by mass of a component B and 0-20 parts by mass of a component C; the component A is a cyclohexane liquid crystal compound shown as a formula I, the component B is a liquid crystal compound shown as a formula VII, and the component C is a liquid crystal compound shown as a formula VI and/or a formula VIII;
in the formula,
R61、R62、R71、R72、R81、R82each of which is any one of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which is optionally substituted by-F, and an alkenyl group having 2 to 12 carbon atoms, which is optionally substituted by-F;
Z6is a single bond or-CH2CH2-；Z7、Z8Are each a single bond, -CH2CH2-、-CH2Any one of O-or-COO-;
M71、M72are respectively-F or-Cl;
n is any one of 1, 2 or 3;
ring A and ring B are each a single bond or
Ring C and ring D are eachAny one of the above; however, when n =1, ring D can only be
The negative dielectric anisotropy liquid crystal composition preferably comprises 5-30 parts by mass of a component A, 45-80 parts by mass of a component B and 0-15 parts by mass of a component C; most preferably 8 to 15 parts of component A, 55 to 65 parts of component B and 4 to 6 parts of component C.
The positive dielectric anisotropy liquid crystal composition and the negative dielectric anisotropy liquid crystal composition can be used for manufacturing liquid crystal elements and electro-optical display elements.
Example 1
Preparation of cyclohexane liquid crystal compound I-1-1:
the synthetic route is as follows:
the preparation process comprises the following steps:
step A:
adding 9.3g (0.05 mol) of 4-ethyl-2, 3-difluorophenylboronic acid, 11.9g (0.06 mol) of 1-bromo-4-propylbenzene, 6.36g (0.06 mol) of anhydrous sodium carbonate, 100ml of toluene, 75ml of ethanol and 75ml of water into a 500ml three-necked bottle, heating to reflux, adding 0.25g (0.0002 mol) of catalyst tetratriphenylphosphine palladium, and keeping reflux for reaction for 6 hours; cooling to room temperature after the reaction is finished, separating liquid, and removing a water layer; the organic phase was passed through a silica gel column and then recrystallized with 2-fold ethanol to obtain 13g of white crystals, i.e., intermediate
And B:
adding 13g (0.05 mol) of the intermediate, 2g of Raney nickel catalyst and 200ml of ethanol into a 500ml high-pressure autoclave, introducing hydrogen until the pressure of the high-pressure autoclave is 3.5-4 Mpa, and carrying out high-pressure hydrogenation reaction for 12 hours at 125 ℃; after the hydrogenation reaction is finished, filtering the catalyst; and (3) spin-drying the obtained filtrate, dissolving the filtrate by using 3 times of petroleum ether, passing through a 50g silica gel column, using the petroleum ether as eluent, and recrystallizing the eluent by using 2 times of absolute ethyl alcohol to finally obtain 12g of a final product, namely the compound I-1-1.
The detection shows that the performance parameters of the obtained product I-1-1 are as follows:
Δn：0.065；m/z：272。
example 2
Preparing cyclohexane liquid crystal compounds I-1-2-I-1-5:
the same procedure as that for the preparation of compound I-1-1 in example 1 was followed, except that: the reaction raw materials used are different from each other,
the starting materials for the preparation of compounds I-1-2 were:
the starting materials for the preparation of compounds I-1-3 were:
the starting materials for the preparation of compounds I-1-4 were:
the starting materials for the preparation of compounds I-1-5 were:
example 3
Preparing cyclohexane liquid crystal compound I-6-1:
the synthetic route is as follows:
the preparation process comprises the following steps:
step a:
adding 500ml of ethanol into a reaction bottle, then adding 25g (1.1 mol) of metallic sodium into the reaction bottle in three batches, heating to reflux, and reacting for 1 h; then keeping the reflux state, slowly dropping 14g (0.1 mol) of 5-ethylcyclohexyl-1, 3-diketone, and carrying out reflux reaction for 0.5h after dropping; then 21g (0.102 mol) of 1-bromo-4-propylcyclohexane is added dropwise, and the reflux reaction is carried out for 5h after the dropwise addition is finished. Slightly cooling after the reaction is finished, pouring the reaction solution into 500ml of water, adding 200ml of ethyl acetate for extraction and layering, evaporating an organic phase to dryness, recrystallizing the obtained solid with 150ml of ethanol, filtering and drying to obtain 20g of a product, namely an intermediate
Step b:
adding 10g (0.038 mol) of the intermediate and 200ml of dichloromethane into a reaction bottle, cooling to 0-4 ℃, adding 25g (0.155 mol) of DAST, and stirring at room temperature for reacting for 38 hours; after the reaction is finished, pouring the reaction solution into 500ml of water, separating the liquid, removing a water layer, evaporating an organic phase to dryness, recrystallizing the obtained solid with 150ml of ethanol, filtering and drying to obtain 5g of a final product, namely the compound I-6-1.
The detection shows that the performance parameters of the obtained product I-6-1 are as follows:
Δn：0.060；m/z：308。
example 4
Preparing cyclohexane liquid crystal compounds I-6-2-I-1-4:
the same procedure as that for the preparation of compound I-6-1 in example 3 was followed, except that: the reaction raw materials used are different from each other,
the raw materials for preparing the compound I-6-2 are as follows:
the starting materials for the preparation of compound I-6-3 were:
the starting materials for the preparation of compounds I-6-4 were:
example 5
The mother liquid crystal used is 1/3 parts1/3 parts ofAnd 1/3 parts ofComposition is carried out;
(1) mixing 10 parts of mother liquid crystal and 1 part of liquid crystal compound shown as a formula I-1-1 to prepare a liquid crystal composition 1-1;
(2) mixing 10 parts of mother liquid crystal and 0.8 part of liquid crystal compound of formula I-1-2 to prepare a liquid crystal composition 1-2;
(3) liquid crystal compositions 1-3 were prepared by mixing 10 parts of the parent liquid crystal and 1 part of the liquid crystal compound of formula I-6-2.
The response speed of the electro-optical characteristics of the mother liquid crystal, the liquid crystal compositions 1 to 1, the liquid crystal compositions 1 to 2 and the liquid crystal compositions 1 to 3 were measured, respectively, and the results of the measurements are shown in Table 1.
The electro-optical characteristic response speed is characterized by the on-time and the off-time measured at an operating voltage of 60Hz + -5V (square wave).
Table 1 example 5 liquid crystal performance test data table
As can be seen from the data in Table 1, the electro-optical response speed of all three liquid crystal compositions to which the cyclohexane-based liquid crystal compound of the present invention was added was significantly reduced as compared with the mother liquid crystal.
Example 6
A cyclohexane-based liquid crystal compound represented by formula I was added to a positive dielectric anisotropic liquid crystal composition, and the response time of the liquid crystal composition was tested.
The response time is a rise time and a fall time measured under the conditions of an applied voltage of 10V, a compensation voltage of 0.1V, and a frequency of 100Hz in a TN cell (TNCell) having a cell gap (CellGaps) of 9 μm. Wherein, the rising time refers to: the time it takes for the dielectric constant to change from 0 to 50% of the maximum dielectric constant at voltage turn-on; the fall time refers to: the time it takes for the dielectric constant to decrease from the maximum dielectric constant to 50% of the maximum dielectric constant when the voltage is off.
(1) Weighing the liquid crystal compounds shown in the following table according to the proportion to prepare a positive dielectric anisotropy liquid crystal composition 2-1;
(2) weighing 90 parts by weight of liquid crystal composition 2-1 and 10 parts by weight of cyclohexane liquid crystal compound I-1Mixing to obtain the positive dielectric anisotropy liquid crystal composition 2-2.
The response times of the liquid crystal compositions 2-1 and 2-2 were measured, respectively, and the results are shown in Table 2.
Table 2 example 6 liquid crystal performance test data table
| Liquid crystal to be tested | Rise time | Time of fall |
| Liquid crystal composition 2-1 | 3.5 milliseconds | 12.0 ms |
| Liquid crystal composition 2-2 | 2.8 milliseconds | 5.7 milliseconds |
As can be seen from the data in Table 2, the addition of the cyclohexane-based liquid crystal compound of the present invention to the positive dielectric anisotropic liquid crystal composition 2-1 can effectively reduce the response time of the liquid crystal composition.
Example 7
A cyclohexane-based liquid crystal compound represented by formula I was added to a negative dielectric anisotropy liquid crystal composition, and the response time of the liquid crystal composition was tested.
The response time measurement was a rise time and a fall time measured under the conditions of a gap of 9 μm, an applied voltage of 10V in a vertically aligned liquid crystal test cell, a frequency of 32HZ, and 300 milliseconds (msec) of a square wave. Wherein, the rising time refers to: the time it takes for the dielectric constant to change from 0 to 50% of the maximum dielectric constant at voltage turn-on; the fall time refers to: the time it takes for the dielectric constant to decrease from the maximum dielectric constant to 50% of the maximum dielectric constant when the voltage is off.
A first group:
(1) weighing the liquid crystal compounds shown in the following table according to the proportion to prepare a negative dielectric anisotropy liquid crystal composition 3-1;
(2) weighing 90 parts by weight of liquid crystal composition 3-1 and 10 parts by weight of cyclohexane liquid crystal compound I-1Mixing to obtain liquid crystal composition 3-2;
(3) weighing 90 parts by weight of liquid crystal composition 3-1 and 10 parts by weight of cyclohexane liquid crystal compound I-6-1Mixing to obtain liquid crystal composition 3-3.
The response times of the liquid crystal composition 3-1, the liquid crystal composition 3-2 and the liquid crystal composition 3-3 were measured, respectively, and the results of the measurements are shown in Table 3.
Table 3 example 7 first set of liquid crystal performance test data table
| Liquid crystal to be tested | Rise time | Time of fall |
| Liquid crystal composition 3-1 | 33 ms | 54 milliseconds |
| Liquid crystal composition 3-2 | 20 milliseconds | 26 milliseconds |
| Liquid crystal composition 3-3 | 21 ms | 29 ms |
Second group:
(1) weighing the liquid crystal compounds shown in the following table according to the proportion to prepare a negative dielectric anisotropy liquid crystal composition 4-1;
(2) weighing 90 parts by weight of liquid crystal composition 4-1 and 10 parts by weight of cyclohexane liquid crystal compound I-1Mixing to obtain liquid crystal composition 4-2;
the response times of the liquid crystal compositions 4-1 and 4-2 were measured, respectively, and the results are shown in Table 4.
Table 4 example 7 second set of liquid crystal performance test data table
| Liquid crystal to be tested | Rise time | Time of fall |
| Liquid crystal composition 4-1 | 27 milliseconds | 40 milliseconds |
| Liquid crystal composition 4-2 | 22 milliseconds | 32 milliseconds |
Third group:
(1) weighing the liquid crystal compounds shown in the following table according to the proportion to prepare a negative dielectric anisotropy liquid crystal composition 5-1;
(2) weighing 5-1 parts of liquid crystal composition and 10 parts of cyclohexane liquid crystal compound I-1 by weightMixing to obtain liquid crystal composition 5-2;
the response times of the liquid crystal compositions 5-1 and 5-2 were measured, respectively, and the results are shown in Table 5.
Table 5 example 7 table of data for testing performance of third group of liquid crystal
| Liquid crystal to be tested | Rise time | Time of fall |
| Liquid crystal composition5-1 | 45 milliseconds | 67 milliseconds |
| Liquid crystal composition 5-2 | 25 milliseconds | 37 milliseconds |
And a fourth group:
(1) weighing the liquid crystal compounds shown in the following table according to the proportion to prepare a negative dielectric anisotropy liquid crystal composition 6-1;
(2) weighing 90 parts by weight of liquid crystal composition 6-1 and 10 parts by weight of cyclohexane liquid crystal compound I-1Mixing to obtain liquid crystal composition 6-2;
the response times of the liquid crystal composition 6-1 and the liquid crystal composition 6-2 were measured, respectively, and the results of the measurements are shown in Table 6.
Table 6 table of data for testing fourth group of liquid crystal of example 7
| Liquid crystal to be tested | Rise time | Time of fall |
| Liquid crystal composition 6-1 | 38 milliseconds | 62 ms |
| Liquid crystal composition 6-2 | 28 ms | 39 milliseconds |
As can be seen from the data in tables 3 to 6, the addition of the cyclohexane-based liquid crystal compound of the present invention to four groups of liquid crystal compositions with different negative dielectric anisotropy can effectively reduce the response time of the liquid crystal compositions; both the rise time and the fall time are significantly shortened.
In the following examples 8 to 14, liquid crystal compounds represented by general formulae I, II, III, IV, V, and VI were weighed in proportion, respectively, to prepare positive dielectric anisotropic liquid crystal compositions. The various liquid crystal monomers used may be synthesized by known methods or may be obtained commercially. The liquid crystal composition is prepared by a conventional method, for example, by dissolving liquid crystal monomers of various components in a solvent at a high temperature, mixing, and then evaporating the solvent under a reduced pressure to obtain a liquid crystal composition; or mixing the liquid crystal monomers in proportion by adopting methods such as heating, ultrasonic wave, suspension and the like. The obtained liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test.
The monomer structure, the amount (parts by mass) of the specific compound, and the results of the performance parameter tests of the obtained liquid crystal composition are shown in the table. Tables 7 to 13 correspond to examples 8 to 14.
TABLE 7 component ratios and performance parameters for the liquid crystal composition of example 8
TABLE 8 component ratios and performance parameters for the liquid crystal composition of example 9
TABLE 9 component ratios and performance parameters for the liquid crystal composition of example 10
TABLE 10 component ratios and performance parameters for the liquid crystal compositions of example 11
TABLE 11 component ratios and performance parameters for the liquid crystal composition of example 12
TABLE 12 component ratios and performance parameters for the liquid crystal compositions of example 13
TABLE 13 component ratios and performance parameters for the liquid crystal composition of example 14
As can be seen from the performance parameters shown in examples 8 to 14, the positive dielectric anisotropy liquid crystal composition of the invention has moderate birefringence, properly high positive dielectric anisotropy, very low rotational viscosity and very fast response time, can bring good visual experience to viewers, and is very suitable for preparing TN mode, IPS mode liquid crystal displays and liquid crystal display elements with fast response, especially for preparing liquid crystal display elements for high definition TV and 3D display.
In the following examples 15 to 21, liquid crystal compounds represented by general formulas I, VII, VI, and VIII were weighed in proportion, respectively, to prepare negative dielectric anisotropic liquid crystal compositions. The liquid crystal monomer sources, the liquid crystal composition preparation methods, and the detection methods used in the following examples were the same as those of the monomer sources, the preparation methods, and the detection methods described in examples 8 to 14.
The monomer structure, the amount (parts by mass) of the specific compound, and the results of the performance parameter tests of the obtained liquid crystal composition are shown in the table. Tables 14 to 20 correspond to examples 15 to 21.
TABLE 14 component ratios and performance parameters for the liquid crystal compositions of example 15
TABLE 15 component ratios and performance parameters for the liquid crystal compositions of example 16
TABLE 16 component ratios and performance parameters for the liquid crystal compositions of example 17
TABLE 17 component ratios and performance parameters for the liquid crystal compositions of example 18
TABLE 18 component ratios and performance parameters for the liquid crystal compositions of example 19
TABLE 19 component ratios and performance parameters for the liquid crystal compositions of example 20
TABLE 20 component ratios and performance parameters for the liquid crystal compositions of example 21
From the performance parameters shown in examples 15 to 21, it can be seen that the negative dielectric anisotropy liquid crystal composition of the present invention has a fast response speed, a short response time, a moderate birefringence, a suitably high negative dielectric anisotropy, and a very low rotational viscosity, can provide good visual experience for viewers, and is very suitable for preparing VA mode liquid crystal displays and liquid crystal display elements with fast response, especially for preparing liquid crystal display elements for high definition TV and 3D display.
Although the present invention has been described with reference to the positive dielectric anisotropic liquid crystal compositions of examples 8 to 14 and the negative dielectric anisotropic liquid crystal compositions of examples 15 to 21, the specific component types and amounts of the liquid crystal compositions were given and tested. However, in addition to the above examples, the object of the present invention can be achieved by using a plurality of liquid crystal compounds according to the present invention and appropriately adjusting the amounts thereof, and a liquid crystal composition having a short response time and a high response speed can be obtained.
Claims (4)
1. A cyclohexane-based liquid crystal compound characterized by: the cyclohexane liquid crystal compound is one or more of liquid crystal compounds shown in formulas I-1 to I-6,
wherein,
Z11、Z12is any one group of single bond, -OCO-or-OOC-respectively;
R11、R12each is any of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, vinyl, allyl, butenyl, ethynyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl, perfluoromethyl, perfluoroethyl, perfluoropropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, perfluorovinyl, perfluoroallyl, isopropyl, 1-methylpropyl, 2-butylmethyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, and 1-methylpentyl.
2. The cyclohexane-based liquid crystal compound according to claim 1, wherein: the liquid crystal compound shown in the formula I-1 is one or more of liquid crystal compounds shown in formulas I-1-1 to I-1-5,
the liquid crystal compound shown in the formula I-6 is one or more of liquid crystal compounds shown in formulas I-6-1 to I-6-4,
3. a positive dielectric anisotropic liquid crystal composition comprising the cyclohexane-based liquid crystal compound according to any one of claims 1 to 2, wherein: the liquid crystal composition comprises 8-15 parts by mass of a first component, 55-65 parts by mass of a second component, 20-30 parts by mass of a third component and 4-6 parts by mass of a fourth component; the first component is one or more of liquid crystal compounds shown in formulas I-1 to I-6, the second component is at least one of liquid crystal compounds shown in formulas II, III and IV, the third component is a liquid crystal compound shown in formula V, and the fourth component is a liquid crystal compound shown in formula VI;
in the formula,
R2、R3、R4、R5each is an alkyl group having 1 to 9 carbon atoms;
R61、R62each of which is any one of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, an alkyl group having 2 to 12 carbon atoms, which is optionally substituted by-F, and an alkenyl group having 2 to 12 carbon atoms, which is optionally substituted by-F;
M2、M3、M41、M42are each-H or-F, M5is-F or-OCF3；
Z6Is a single bond or-CH2CH2-。
4. A negative dielectric anisotropic liquid crystal composition comprising the cyclohexane-based liquid crystal compound according to any one of claims 1 to 2, wherein: the liquid crystal composition comprises 8-15 parts by mass of a component A, 55-65 parts by mass of a component B and 4-6 parts by mass of a component C; the component A is one or more of liquid crystal compounds shown in formulas I-1 to I-6, the component B is a liquid crystal compound shown in a formula VII, and the component C is a liquid crystal compound shown in a formula VI and/or a formula VIII;
in the formula,
R61、R62、R71、R72、R81、R82respectively is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms or an alkenyloxy groupAny one of an alkyl group having 2 to 12 carbon atoms wherein-H is substituted with-F, and an alkenyl group having 2 to 12 carbon atoms wherein-H is substituted with-F;
Z6is a single bond or-CH2CH2-；Z7、Z8Are each a single bond, -CH2CH2-、-CH2Any one of O-or-COO-;
M71、M72are respectively-F or-Cl;
n is any one of 1, 2 or 3;
the ring A and the ring B are respectively a single bond,Any one of the above;
ring C and ring D are eachAny one of the above; when n is 1, however, ring D can only be
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