CN105130767A - Liquid crystal compound containing methylbenzene and difluoro methyleneoxy linking group and preparing method and application thereof - Google Patents
Liquid crystal compound containing methylbenzene and difluoro methyleneoxy linking group and preparing method and application thereof Download PDFInfo
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- CN105130767A CN105130767A CN201510555507.8A CN201510555507A CN105130767A CN 105130767 A CN105130767 A CN 105130767A CN 201510555507 A CN201510555507 A CN 201510555507A CN 105130767 A CN105130767 A CN 105130767A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 120
- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 125000005647 linker group Chemical group 0.000 title claims abstract description 29
- 125000005701 difluoromethyleneoxy group Chemical group FC(F)([*:1])O[*:2] 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- -1 hydrogen trifluoride Chemical class 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- 230000004224 protection Effects 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000012047 saturated solution Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 description 13
- 0 Cc1c(*C*I)cc(*)c(*)c1*I Chemical compound Cc1c(*C*I)cc(*)c(*)c1*I 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 239000000178 monomer Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MBXXQYJBFRRFCK-UHFFFAOYSA-N benzyl fluoride Chemical compound FCC1=CC=CC=C1 MBXXQYJBFRRFCK-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- YXLICHFWQJEIDU-CLFYSBASSA-N C/C(/C(O)=C)=C(\CC=C)/CF Chemical compound C/C(/C(O)=C)=C(\CC=C)/CF YXLICHFWQJEIDU-CLFYSBASSA-N 0.000 description 1
- CKIFCLWOFBYZGS-UHFFFAOYSA-N CCC(C(C)C1F)=CC=C1F Chemical compound CCC(C(C)C1F)=CC=C1F CKIFCLWOFBYZGS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BOYQCJIIDRSQLZ-UHFFFAOYSA-N Cc(c(F)c(cc1)F)c1O Chemical compound Cc(c(F)c(cc1)F)c1O BOYQCJIIDRSQLZ-UHFFFAOYSA-N 0.000 description 1
- HRHNVHOYBRELCI-UHFFFAOYSA-N Fc1cc(-c2ccc(C(CC3)CCC3C3CCCC3)cc2)cc(F)c1C1=SCCCS1 Chemical compound Fc1cc(-c2ccc(C(CC3)CCC3C3CCCC3)cc2)cc(F)c1C1=SCCCS1 HRHNVHOYBRELCI-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- 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
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- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- 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
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- 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
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- 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
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Abstract
The invention discloses a liquid crystal compound containing methylbenzene and a difluoro methyleneoxy linking group and a preparing method and application thereof. The compound is shown as the formula I. According to the molecular structure of the compound in the formula I, the liquid crystal compound containing the methylbenzene and the difluoro methyleneoxy (-CF2O-) linking group is high in dielectric anisotropy and has low viscosity and excellent low-temperature intersolubility more importantly, and the performance is of great significance in liquid crystal compound blending.
Description
Technical Field
The invention relates to the field of preparation and application of liquid crystal compounds, in particular to a liquid crystal compound containing methylbenzene and difluorometheneoxy linking groups, and a preparation method and application thereof.
Background
At present, the application range of liquid crystal compounds is expanding more and more, and the liquid crystal compounds can be applied to various displays, electro-optical devices, sensors and the like. The liquid crystal compounds used in the above display fields are various, and nematic liquid crystals are most widely used. Nematic liquid crystals have been applied in passive TN, STN matrix displays and systems with TFT active matrix.
Although the market for thin film transistor technology (TFT-LCD) applications is very large and the technology is mature in recent years, the demand for display technology is continuously increasing, especially in the aspects of achieving fast response, reducing driving voltage to reduce power consumption, etc. The liquid crystal material is one of important photoelectronic materials for liquid crystal displays, and plays an important role in improving the performance of the liquid crystal displays.
As liquid crystal materials, good chemical and thermal stability as well as stability to electric fields and electromagnetic radiation are required. As a liquid crystal material for thin film transistor (TFT-LCD) technology, it is required to have not only the above stability, but also a wide nematic phase temperature range, a suitable birefringence anisotropy, a very high resistivity, a good uv resistance, a high charge retention rate, and a low vapor pressure.
For a dynamic picture display application such as a liquid crystal television, in order to realize high quality display, eliminate display image sticking and tailing, the liquid crystal is required to have a fast response speed, and thus the liquid crystal is required to have a low rotational viscosity γ1(ii) a In addition, in order to reduce the power consumption of the device, it is desirable that the driving voltage of the liquid crystal is as low as possible, so that it is important to increase the dielectric anisotropy Δ of the liquid crystal for the mixed liquid crystal.
A great deal of research shows that the liquid crystal molecule introduces a difluoromethyleneoxy (-CF)2After the O-) linking group, the rotational viscosity gamma of the liquid crystal is increased1And is reduced. In addition, due to difluoromethyleneoxy (-CF)2The contribution of dipole moment of O-) bridge and the dipole moment of terminal fluorine atom are increased to some extent, so that the dielectric anisotropy delta of liquid crystal molecule is increased. German Merck and Japanese Kohyo corporation (CN1717468A, CN101143808A, CN101157862A, etc.) have disclosed that certain compounds having difluoromethyleneoxy (-CF) have various substituents2A liquid crystal compound having an O-) linking group. But (-CF)2The introduction of the O-) group can greatly reduce the clearing point of the liquid crystal. When the liquid crystal mixture is prepared, more viscosity needs to be addedHigh clearing Point Compound of formula (I) (-CF)2The clearing point caused by the O-) group is reduced, thereby restricting the space for improving the response speed of the liquid crystal mixture.
The liquid crystal is used as a core functional material of the liquid crystal display device, in order to meet the requirements of various performance parameters of the liquid crystal display device and to adapt to the process requirements of the liquid crystal display device, the liquid crystal material is required to have a wide variety of performance parameters, and any one monomer liquid crystal material cannot meet all the requirements, so that monomer liquid crystals with different performances are required to be synthesized, and the characteristics required by the LCD device are met by a method for blending mixed liquid crystals.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a liquid crystal compound containing methylbenzene and a difluoromethyleneoxy linking group, and a preparation method and application thereof, so as to solve the problem that the clearing point of the existing liquid crystal compound with the difluoromethyleneoxy is reduced and improve the response speed of a liquid crystal mixture.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a liquid crystal compound containing methylbenzene and difluoromethyleneoxy linking group, the structural formula of the compound is shown as the general formula I,
wherein,
r is selected from any one of the following groups:
firstly, selecting cyclopentyl, cyclobutyl, cyclopropyl, straight-chain alkyl with 1-10 carbon atoms, fluorine-substituted straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms and fluorine-substituted straight-chain alkoxy with 1-10 carbon atoms;
② the first step contains-CH2At least one-CH of any of-2-a group substituted with one of the following groups: -CH ═ CH-, -C ≡ C-, -COO-, -OOC-, or-O-;
is selected from Any one of the groups;
is selected from Any one of the groups;
X1、X3any one selected from H, F;
X2selected from any one of the following groups (1), (2) and (3),
(1)H、F，
(2) a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, a linear alkenyloxy group having 2 to 10 carbon atoms,
(3) a group obtained by substituting one or more H in the above (2) with F;
X1、X2、X3f is not simultaneously obtained;
n is selected from 1 or 2 or 3.
The technical scheme of the invention is further improved as follows: the compound shown in the general formula I is a compound shown in formulas I-1 to I-3,
the technical scheme of the invention is further improved as follows: the compound shown in the general formula I is a compound shown in formulas I-1-1 to I-3-1,
the technical proposal of the invention also discloses a preparation method of the liquid crystal compound containing methylbenzene and difluorometheneoxy linking group,
the synthetic route of the compound shown in the general formula I is as follows,
specifically comprises the following two steps of a and b,
a) mixing the raw materialsDissolving in toluene, addingHeating to 60 ℃ under stirring, and dripping CF3SO3H, heating to reflux after adding, dividing water, refluxing for 12 hours, cooling, evaporating toluene to dryness, adding methyl tert-butyl ether for washing, and performing suction filtration to obtain a product
b) Subjecting the product obtained in the step 1 toDissolving with dichloromethane, cooling to-75 deg.C under the protection of inert gas, adding triethylamine andafter the addition of the dichloromethane solution, the reaction is carried out for 1 hour under the condition of heat preservation, hydrogen trifluoride and triethylamine are dropwise added, the reaction is carried out for 30 minutes under the condition of heat preservation, and then Br is dropwise added2Naturally heating to-20 ℃ after dropping and keeping the temperature for reaction for 30 minutes, pouring the reaction solution into a saturated solution of sodium bicarbonate, separating the solution, extracting, washing with water, passing through a silica gel column, and concentrating to obtain a target product
The technical scheme of the invention further discloses a liquid crystal composition consisting of a liquid crystal compound containing a fluoromethylbenzene and a difluoromethyleneoxy linking group, the liquid crystal composition comprises a component A consisting of a compound shown as a general formula I, a component B consisting of one or two compounds shown as a general formula II, and a component C consisting of three to ten compounds shown as a general formula III, wherein the mass ratio of the component A to the component B to the component C is 1-40: 5-80,
wherein,
R1、R2selected from the number of carbon atomsIs any one of a straight-chain alkyl group of 1 to 6 and a straight-chain alkenyl group of 2 to 6 carbon atoms;
R3any one selected from H, F and straight-chain alkyl groups with 1-6 carbon atoms;
any one or more selected from 1, 4-cyclohexylene, 1, 4-phenylene and fluoro-1, 4-phenylene;
p is 2 or 3;
(F) represents H or F.
The technical scheme of the invention is further improved as follows: the compound shown in the general formula II is specifically a compound shown in a formula II-1 to a formula II-9,
the technical scheme of the invention is further improved as follows: the compound shown in the general formula III is specifically a compound shown in a formula III-1 to a formula III-11,
the technical scheme of the invention is further improved as follows: the mass ratio of the component A, the component B and the component C in the liquid crystal composition is 10-35: 15-35: 25-75.
The technical scheme of the invention is further improved as follows: the liquid crystal composition further comprises an additive which accounts for not more than 0.05 percent of the weight of the liquid crystal composition, and the additive is at least one of an antioxidant, an anti-ultraviolet agent and a chiral agent.
Due to the adoption of the technical scheme, the invention has the technical progress that:
the liquid crystal compound containing methylbenzene and difluorometheneoxy linking group has a wide application range. Can be used as a base material for liquid crystal mixtures, or can be added as an additive to liquid crystal base materials composed of other types of compounds, for example to improve the dielectric anisotropy Δ/rotational viscosity γ of liquid crystal mixtures1Threshold voltage VthContrast at low temperature/optical anisotropy Δ n/clearing point Cp.
Response speed t of liquid crystal composition, thickness d of liquid crystal box and rotational viscosity gamma of liquid crystal1According to t-1d2Has a lower rotational viscosity γ1The response time of the liquid crystal of (3) is short. The liquid crystal compound containing the fluoro methyl benzene and the difluoromethyleneoxy linking group provided by the invention contains the fluoro methyl benzene and the difluoromethyleneoxy (-CF) in the molecular structure2The liquid crystal compound of the O-) linking group not only has larger dielectric anisotropy delta, but also has faster response speed t and lower rotational viscosity gamma1And good low-temperature intersolubility, which is of great significance for the preparation of liquid crystal mixtures.
The pure compound shown in the general formula I is colorless and shows higher stability to light, heat and chemical. In particular, the compound shown in the general formula I shows large dielectric anisotropy delta and good low-temperature performance, such as response speed and contrast at low temperature, and also has the advantage of inhibiting the formation of a smectic phase, which indicates that the liquid crystal composition using the compound shown in the general formula I has better low-temperature storage stability.
The invention also provides an application of the liquid crystal compound containing the methylbenzene and the difluoro methyleneoxy linking group and the liquid crystal composition composed of the liquid crystal compound containing the methylbenzene and the difluoro methyleneoxy linking group in the preparation of a liquid crystal display device material or an electro-optical display device material, and the liquid crystal display device material or the electro-optical display device material containing the liquid crystal compound containing the methylbenzene and the difluoro methyleneoxy linking group or the liquid crystal composition, and belongs to the protection scope of the invention.
Detailed Description
The invention discloses a liquid crystal compound containing methylbenzene and difluoromethyleneoxy linking group, the structural formula of the compound is shown as the general formula I,
wherein,
r is selected from any one of the following groups:
firstly, selecting cyclopentyl, cyclobutyl, cyclopropyl, straight-chain alkyl with 1-10 carbon atoms, fluorine-substituted straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms and fluorine-substituted straight-chain alkoxy with 1-10 carbon atoms;
② the first step contains-CH2At least one-CH of any of-2-a group substituted with one of the following groups: -CH ═ CH-, -C ≡ C-, -COO-, -OOC-, or-O-;
is selected from Any one of the groups;
is selected from Any one of the groups;
X1、X3any one selected from H, F;
X2selected from any one of the following groups (1), (2) and (3),
(1)H、F，
(2) a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, a linear alkenyloxy group having 2 to 10 carbon atoms,
(3) a group obtained by substituting one or more H in the above (2) with F;
X1、X2、X3f is not simultaneously obtained;
n is selected from 1 or 2 or 3.
Specifically, the compound shown in the general formula I is a compound shown in formulas I-1 to I-3,
the invention also discloses a preparation method of the liquid crystal compound containing methylbenzene and difluorometheneoxy linking group,
the synthetic route of the compound shown in the general formula I is as follows,
key intermediate for synthesizing compound shown as general formula IAndthe method can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the silica gel column passing, the recrystallization purification and other means are well known by the synthesizers in the field, and the synthesis process can be completely realized to obtain the target product according to the following description.
The invention further discloses a liquid crystal composition consisting of a liquid crystal compound containing methylbenzene and a difluoromethyleneoxy linking group, the liquid crystal composition comprises a component A consisting of a compound shown as a general formula I, a component B consisting of one or two compounds shown as a general formula II, and a component C consisting of three to ten compounds shown as a general formula III, wherein the mass ratio of the component A to the component B to the component C is 1-40: 5-80,
wherein,
R1、R2any one selected from linear alkyl with 1-6 carbon atoms and linear alkenyl with 2-6 carbon atoms;
R3any one selected from H, F and straight-chain alkyl groups with 1-6 carbon atoms;
any one or more selected from 1, 4-cyclohexylene, 1, 4-phenylene and fluoro-1, 4-phenylene;
p is 2 or 3;
(F) represents H or F.
Preferably, the mass ratio of the component A, the component B and the component C is 10-35: 15-35: 25-75. More preferably, the mass ratio of the component A, the component B and the component C is 5-10: 25: 75, and the mass ratio of the component A, the component B and the component C is 5: 25: 75 or 10: 25: 75.
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
In the following examples GC means gas chromatographic purity and MP means melting point.
Δ represents dielectric anisotropy, Δ ═// -, where// is the dielectric constant parallel to the molecular axis, and ×) is the dielectric constant perpendicular to the molecular axis, with test conditions of 25 ± 0.5 ℃; 1 KHz; HP 4284A; 5.2 micron TN left-handed cassette.
Δ n represents optical anisotropy, and Δ n ═ ne, where no is the refractive index of ordinary light and ne is the refractive index of extraordinary light, and the test conditions were 589nm, 25 ± 0.5 ℃.
γ1The rotational viscosity is expressed in mPas, the test conditions are 25 +/-0.5 ℃.
VHR: voltage holding ratio (%) under the test conditions of 20 + -2 deg.C, voltage + -5V, pulse width 10ms, and voltage holding time 16.7 ms. The test equipment is a TOYOModel6254 liquid crystal performance comprehensive tester.
Cp: the unit ℃ represents the clearing point of the liquid crystal. Cp represents the clearing point, which can be directly measured, and for compounds that cannot be directly measured, the fitting data can be calculated as follows:
in the process of preparing the mixed liquid crystal, a plurality of proper monomer liquid crystals are selected for mixing, so that a eutectic mixture can be formed, and the melting point of the liquid crystal is effectively reduced; meanwhile, the clearing point of the mixed liquid crystal can be improved by adding the monomer liquid crystal with the high clearing point, so that the mixed liquid crystal with the nematic phase temperature range meeting the requirement is prepared, and the clearing point and the concentration of the mixed liquid crystal and the monomer liquid crystal meet the following relational expression:
Tc＝∑XiTi
wherein Tc represents the clearing point of the mixed liquid crystal, XiDenotes the concentration of monomeric liquid crystal in the mixed liquid crystal, TiIndicating the clearing point of the monomeric liquid crystal.
Examples 1 to 4 are examples of the preparation of liquid crystal compounds. The progress of the reaction is generally monitored by TLC, and the post-treatment after the completion of the reaction is generally water washing, extraction, combination of organic phases, drying, evaporation of the solvent under reduced pressure, recrystallization, and column chromatography, and those skilled in the art can implement the present invention as described below.
Example 1
The liquid crystal compound shown in the formula I-1-4-1 is prepared, the structural formula is shown as follows,
the synthetic route is as follows,
specifically comprises the following two steps 1-a) and 1-b),
1-a) 229g (0.83mol) of starting materialDissolved in 1.5L of toluene, to which 108g (1mol) of toluene were addedThe temperature was raised to 60 ℃ with stirring, and 150g (1mol) of trifluoromethanesulfonic acid (CF) were added dropwise3SO3H) Heating to reflux after adding, dividing water, reflux reacting for 12 hours, cooling, evaporating toluene, adding 1L methyl tert-butyl ether for washing, and suction filtering to obtain 250g productThe yield thereof was found to be 50%.
1-b) 240g (0.48mol) from step 1-a)Dissolving with 1L dichloromethane, cooling to-75 deg.C under the protection of inert gas, and adding 97g (0.96mol) triethylamine and 88g (0.5mol) dropwiseAfter completion of the addition, the reaction was allowed to proceed for 1 hour under heat, and 161g (1.44mol) of triethylamine trifluoride (NEt) was added dropwise thereto33HF), the incubation was continued for 30 minutes and 160g (1.44mol) of Br were added dropwise2After dropping and keeping the temperature for reaction for 30 minutes, naturally heating to-20 ℃, pouring the reaction solution into 1L of saturated solution of sodium bicarbonate, separating, extracting, washing with water, passing through a silica gel column, and concentrating to obtain 30g of target productGC: 99.80% and yield 15%.
Example 2
The liquid crystal compound shown in the formula I-1-14-1 is prepared, the structural formula is shown as follows,
the synthetic route is as follows,
specifically comprises the following two steps of 2-a) and 2-b),
2-a) mixingAlternative example 1 in step 1-a)Obtaining the product
2-b) mixingAlternative example 1 in step 1-b)Will be provided withSubstitutionObtaining the target productGC：99.82％。
Example 3
The liquid crystal compound shown in the formula I-2-3-1 is prepared, the structural formula is shown as follows,
the synthetic route is as follows,
specifically comprises the following two steps of 3-a) and 3-b),
3-a) mixingAlternative example 1 in step 1-a)Obtaining the product
b) Will be provided withAlternative example 1 in step 1-b)Obtaining the target productGC：99.85％。
Example 4
The liquid crystal compound shown in the formula I-2-8-1 is prepared, the structural formula is shown as follows,
the synthetic route is as follows,
specifically comprises the following two steps of 4-a) and 4-b),
4-a) mixingAlternative example 1 in step 1-a)Obtaining the product
4-b) mixingAlternative example 1 in step 1-b)Obtaining the target productGC：99.84％。
The performance parameters of the liquid crystal compounds prepared in examples 1 to 4 are shown in the following table.
Example 5
A liquid crystal composition M1 was prepared in accordance with the following mass ratios of the respective components.
A liquid crystal composition M1 was prepared by mixing 25 parts by mass of a liquid crystal compound represented by the general formula II constituting component B and the following parts by mass of a compound represented by the general formula III constituting component C in a mass ratio of 25: 75 between component B and component C.
Example 6
A liquid crystal composition a was prepared in the following mass ratios of the respective components.
Example 7
In the same manner as in example 6, only component A was replaced with an equal part by mass of the compoundA liquid-crystal mixture b was obtained.
Example 8
In the same manner as in example 6, only component A was replaced with an equal part by mass of the compoundA liquid-crystal mixture c was obtained.
The results of the performance tests of the liquid crystal compositions of examples 5 to 8 are shown in the following table.
| Liquid crystal composition | Δn | Δε | Cp | γ1 |
| M1 | 0.100 | 10.6 | 95 | 130.0 |
| a | 0.096 | 11.5 | 86 | 120.5 |
| b | 0.106 | 11.3 | 94 | 123.0 |
| c | 0.104 | 11.1 | 95 | 126.0 |
Through the performance data of the liquid crystal compositions in the embodiments 5 to 8, it can be seen that the compound of the formula I provided by the invention has a larger dielectric anisotropy delta, a faster response speed t and a lower rotational viscosity gamma1The liquid crystal compound of the invention is also proved to have good low-temperature intersolubility, and the performance has important significance for preparing liquid crystal mixtures.
Claims (9)
1. A liquid crystal compound containing a methylbenzene and difluoromethyleneoxy linking group, characterized in that: the structural formula of the compound is shown in a general formula I,
wherein,
r is selected from any one of the following groups:
firstly, selecting cyclopentyl, cyclobutyl, cyclopropyl, straight-chain alkyl with 1-10 carbon atoms, fluorine-substituted straight-chain alkyl with 1-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms and fluorine-substituted straight-chain alkoxy with 1-10 carbon atoms;
② the first step contains-CH2At least one-CH of any of-2-a group substituted with one of the following groups: -CH ═ CH-, -C ≡ C-, -COO-, -OOC-, or-0-;
is selected from Any one of the groups;
is selected from Any one of the groups;
X1、X3any one selected from H, F;
X2selected from any one of the following groups (1), (2) and (3),
(1)H、F，
(2) a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, a linear alkenyloxy group having 2 to 10 carbon atoms,
(3) a group obtained by substituting one or more H in the above (2) with F;
X1、X2、X3f is not simultaneously obtained;
n is selected from 1 or 2 or 3.
2. The liquid crystal compound having a methyl benzene and difluoromethyleneoxy linking group of claim 1, wherein: the compound shown in the general formula I is a compound shown in formulas I-1 to I-3,
3. the liquid crystal compound having a methyl benzene and difluoromethyleneoxy linking group of claim 2, wherein: the compound shown in the general formula I is a compound shown in formulas I-1-1 to I-3-1,
4. a method for preparing a liquid crystal compound containing a methylbenzene and difluoromethyleneoxy linking group, characterized in that:
the synthetic route of the compound shown in the general formula I is as follows,
specifically comprises the following two steps of a and b,
a) mixing the raw materialsDissolving in toluene, addingHeating to 60 ℃ under stirring, and dripping CF3SO3H, heating to reflux after adding, dividing water, refluxing for 12 hours, cooling, evaporating toluene to dryness, adding methyl tert-butyl ether for washing, and performing suction filtration to obtain a product
b) Subjecting the product obtained in the step 1 toDissolving with dichloromethane, cooling to-75 deg.C under the protection of inert gas, adding triethylamine andafter the addition of the dichloromethane solution, the reaction is carried out for 1 hour under the condition of heat preservation, hydrogen trifluoride and triethylamine are dropwise added, the reaction is carried out for 30 minutes under the condition of heat preservation, and then Br is dropwise added2Naturally heating to-20 ℃ after dropping and keeping the temperature for reaction for 30 minutes, pouring the reaction solution into a saturated solution of sodium bicarbonate, separating the solution, extracting, washing with water, passing through a silica gel column, and concentrating to obtain a target product
5. A liquid crystal composition comprising a liquid crystal compound having a methylbenzene and difluoromethyleneoxy linking group, characterized in that: the liquid crystal composition comprises a component A consisting of compounds shown in a general formula I, a component B consisting of one or two compounds shown in a general formula II, and a component C consisting of three to ten compounds shown in a general formula III, wherein the mass ratio of the component A to the component B to the component C is 1-40: 5-80,
wherein,
R1、R2any one selected from linear alkyl with 1-6 carbon atoms and linear alkenyl with 2-6 carbon atoms;
R3any one selected from H, F and straight-chain alkyl groups with 1-6 carbon atoms;
any one or more selected from 1, 4-cyclohexylene, 1, 4-phenylene and fluoro-1, 4-phenylene;
p is 2 or 3;
(F) represents H or F.
6. The liquid crystal composition comprising a liquid crystal compound containing a methyl benzene and difluoromethyleneoxy linking group according to claim 5, wherein: the compound shown in the general formula II is specifically a compound shown in a formula II-1 to a formula II-9,
7. the liquid crystal composition comprising a liquid crystal compound containing a methyl benzene and difluoromethyleneoxy linking group according to claim 5, wherein: the compound shown in the general formula III is specifically a compound shown in a formula III-1 to a formula III-11,
8. the liquid crystal composition comprising a liquid crystal compound containing a methyl benzene and difluoromethyleneoxy linking group according to claim 5, wherein: the mass ratio of the component A, the component B and the component C in the liquid crystal composition is 10-35: 15-35: 25-75.
9. The liquid crystal composition comprising a liquid crystal compound containing a methyl benzene and difluoromethyleneoxy linking group according to claim 8, wherein: the liquid crystal composition further comprises an additive which accounts for not more than 0.05 percent of the weight of the liquid crystal composition, and the additive is at least one of an antioxidant, an anti-ultraviolet agent and a chiral agent.
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| CN107760316A (en) * | 2017-09-30 | 2018-03-06 | 烟台显华化工科技有限公司 | Liquid-crystal compounds containing the methyl substituents benzene of 3 fluorine 5 and difluoromethylenedioconnecting linking group and preparation method and application |
| CN110467927A (en) * | 2018-05-11 | 2019-11-19 | 石家庄诚志永华显示材料有限公司 | Replace the difluoromethoxy bridge liquid-crystal compounds and liquid-crystal composition of 2,3- difluorophenyl containing methyl |
| CN111286343A (en) * | 2020-02-12 | 2020-06-16 | 华南师范大学 | Bis-difluoromethoxy bridged biphenyl liquid crystal compound substituted by bis-fluorine-containing group as well as preparation method and application thereof |
| CN111748357A (en) * | 2019-03-29 | 2020-10-09 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display device |
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| CN107760316A (en) * | 2017-09-30 | 2018-03-06 | 烟台显华化工科技有限公司 | Liquid-crystal compounds containing the methyl substituents benzene of 3 fluorine 5 and difluoromethylenedioconnecting linking group and preparation method and application |
| CN110467927A (en) * | 2018-05-11 | 2019-11-19 | 石家庄诚志永华显示材料有限公司 | Replace the difluoromethoxy bridge liquid-crystal compounds and liquid-crystal composition of 2,3- difluorophenyl containing methyl |
| CN110467927B (en) * | 2018-05-11 | 2023-05-05 | 石家庄诚志永华显示材料有限公司 | Difluoromethoxy bridge liquid crystal compound containing methyl substituted 2, 3-difluorophenyl and liquid crystal composition |
| CN111748357A (en) * | 2019-03-29 | 2020-10-09 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display device |
| CN111748357B (en) * | 2019-03-29 | 2023-09-05 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display element |
| CN111286343A (en) * | 2020-02-12 | 2020-06-16 | 华南师范大学 | Bis-difluoromethoxy bridged biphenyl liquid crystal compound substituted by bis-fluorine-containing group as well as preparation method and application thereof |
| CN113897202A (en) * | 2021-11-17 | 2022-01-07 | 浙江工业大学 | Difluoromethyleneoxy liquid crystal compound and synthesis method thereof |
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