CN111484853B - Liquid crystal compound and preparation method and application thereof - Google Patents
Liquid crystal compound and preparation method and application thereof Download PDFInfo
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- CN111484853B CN111484853B CN201910084680.2A CN201910084680A CN111484853B CN 111484853 B CN111484853 B CN 111484853B CN 201910084680 A CN201910084680 A CN 201910084680A CN 111484853 B CN111484853 B CN 111484853B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- -1 boric acid ester Chemical class 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005447 environmental material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structure shown as a general formula I, wherein R in the general formula I1Represents cyclopropyl, cyclobutyl or cyclopentyl; z represents a single bond, -O-, -CH2‑、‑CH2CH2-or-CH2O‑；R2represents-CF3or-OCF3；R3Represents H, -CH3or-OCH3. The compound has the characteristics of larger vertical dielectric anisotropy, integral dielectric anisotropy close to 0, lower rotational viscosity, good liquid crystal intersolubility and the like, can be widely applied to the field of liquid crystal display, and has important application value.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and relates to a liquid crystal compound, and a preparation method and application thereof.
Background
In recent years, liquid crystal display devices have been developed more and more rapidly, and various types such as a small liquid crystal display device for vehicles, a portable liquid crystal display device, an ultra-thin liquid crystal display device, and the like have been developed. Taking a television as an example, the television has the characteristics of light weight, small occupied space and convenient movement, and is also provided with a notebook personal computer, a mobile phone and the like.
The liquid crystal material is used as an environmental material and has great research value and good application prospect in the fields of information display materials, organic optoelectronic materials and the like. At present, the TFT-LCD product technology has matured, and successfully solves the technical problems of viewing angle, resolution, color saturation, brightness, etc., and large-size and medium-and small-size TFT-LCD displays have gradually occupied the mainstream status of flat panel displays in respective fields. However, the requirements for display technology are continuously increasing, and liquid crystal displays are required to achieve faster response, reduce driving voltage to reduce power consumption, and the like, and liquid crystal materials are also required to have low voltage driving, fast response, wide temperature range and good low temperature stability.
The liquid crystal material plays an important role in improving the performance of the liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the synthesis of a novel structure liquid crystal compound and the research of the structure-performance relationship become important work in the field of liquid crystal.
Disclosure of Invention
The invention aims to provide a liquid crystal compound with a novel structure, which has the characteristics of large vertical dielectric anisotropy, low rotational viscosity, good liquid crystal intersolubility and the like, has the integral dielectric anisotropy close to 0, can be widely applied to the field of liquid crystal display and has important application value.
The liquid crystal compound has the following structure:
in the general formula I, R1Represents cyclopropyl, cyclobutyl or cyclopentyl;
z represents a single bond, -O-, -CH2-、-CH2CH2-or-CH2O-；
R2represents-CF3or-OCF3；
R3Represents H, -CH3or-OCH3。
Preferably, the compound is selected from one of the following compounds:
z in each formula represents a single bond, -O-, -CH2-, -CH2CH 2-or-CH 2O-; r2 represents-CF 3 or-OCF 3.
Further preferably, the compound is selected from one of the following compounds:
still further preferably, the compound is selected from one or more of the following compounds:
most preferably, the compound is selected from one or more of the following compounds:
the second object of the present invention is to provide a method for preparing the liquid crystal compound.
The synthetic route is as follows:
the preparation method comprises the following steps:
1) will be provided with
Metalating with organic lithium reagent, and reacting with boric acid ester to obtain
2)
And
by suzuki reaction, obtaining
3)
Ring closure is carried out under the catalysis of alkali to obtain
Wherein R in the compound involved in each step1、Z、R2、R3With R in the resulting compound product1、Z、R2、R3The groups represented correspond (above).
In the step 1) of the above-mentioned method,
the feeding molar ratio of the organic lithium reagent to the organic lithium reagent is 1: 1.0-2.0, and the feeding molar ratio of the organic lithium reagent to the boric acid ester is 1: 1.0-3.0; the reaction temperature can be between-50 and-100 ℃;
wherein,
are available through public commercial routes; the organic lithium reagent is selected from one or more of sec-butyl lithium, tert-butyl lithium or n-butyl lithium; the boric acid esterOne or more of trimethyl borate, triisopropyl borate, tributyl borate and triisobutyl borate.
In the step 2) of the above method,
and
the feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5; the reaction temperature can be 60-140 ℃;
wherein, the raw materials
Are commercially available through the open.
In the step 3), the step of the method comprises the following steps,
the feeding mol ratio of the alkali and the alkali is 1: 1.0-4.0; the reaction temperature is 80-150 ℃.
The method of the invention, if necessary, involves conventional post-treatment, such as: extracting with dichloromethane, ethyl acetate or toluene, separating liquid, washing with water, drying, evaporating with vacuum rotary evaporator, and purifying the obtained product by vacuum distillation or recrystallization and/or chromatographic separation.
The compound of the invention can be stably and efficiently obtained by the preparation method.
A third object of the invention is to protect compositions containing said compounds. The mass percentage of the compound in the composition is 0.01-60%, preferably 0.1-50%, and more preferably 0.1-40%.
The fourth object of the present invention is to protect the use of said compounds and compositions containing said compounds in the field of liquid crystal displays, preferably in liquid crystal display devices. The liquid crystal display device includes, but is not limited to, a VA, TN, STN, FFS or IPS liquid crystal display.
The liquid crystal compound has larger vertical dielectric anisotropy, larger penetration rate, high clearing point, higher optical anisotropy, moderate rotary viscosity and liquid crystal intersolubility, excellent low-temperature working effect, good thermal stability, chemical stability, optical stability, mechanical property and the like; therefore, the driving voltage is effectively reduced, the response speed of the liquid crystal display device is improved, and the liquid crystal display device has the characteristics of moderate optical anisotropy value, high charge retention rate and the like.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The starting materials are commercially available from the open literature unless otherwise specified.
According to the conventional detection method in the field, various performance parameters of the liquid crystal compound are obtained through linear fitting, wherein the specific meanings of the performance parameters are as follows:
Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz);
ε ^ represents a dielectric constant (25 ℃ C., 1000Hz) in the vertical molecular axis direction.
Example 1
The structural formula of the liquid crystal compound is as follows:
the synthetic route for the preparation of compound BYLC-01 is shown below:
the method comprises the following specific steps:
(1) synthesis of Compound BYLC-01-1:
under the protection of nitrogen, 70g of the mixture is added into a reaction bottle
(0.380mol), 150ml tetrahydrofuran, controlling the temperature to be-70 to-80 ℃, and dropwise adding 0.45mol of n-butyl lithium n-hexane solution, controlling the temperature to react for 1 hour after dripping, controlling the temperature to be minus 60 to minus 70 ℃, dripping 48.0g of trimethyl borate (0.45mol), and naturally returning the temperature to be minus 30 ℃. Acidification was carried out by adding 400ml of 2M aqueous hydrochloric acid solution, and conventional workup and recrystallization from petroleum ether gave 80.1g of a pale yellow solid (compound BYLC-01-1, 0.351mol), HPLC: 99.8%, yield: 92.5 percent.
(2) Synthesis of Compound BYLC-01-2:
80.1g of BYLC-01-1(0.351mol), 90.6g of compound were added to a reaction flask under nitrogen protection
(0.351mol), 200ml of N, N-dimethylformamide, 100ml of deionized water, 72.8g of anhydrous potassium carbonate (0.53mol), 0.5g of tetratriphenylphosphine palladium, and heated to 70 ℃ for reaction for 3 hours. Conventional post-treatment, chromatographic purification, n-hexane elution and ethanol recrystallization gave 98.9g of a white solid (compound BYLC-01-2,0.273mol), 99.8% GC, yield: 77.8 percent.
(3) Synthesis of Compound BYLC-01:
under the protection of nitrogen, 98.9g of compound BYLC-01-2,0.273mol), 200ml of N, N-dimethylformamide and 50g of potassium tert-butoxide are added into a reaction flask, the temperature is controlled at 130 ℃ and the reaction is carried out for 3 hours, and the TLC tracing reaction is complete. Conventional work-up was carried out, purification by chromatography, elution with n-hexane and recrystallization from ethanol gave 62.7g of a white solid (compound BYLC-01, 0.183mol), GC: 99.9 percent and the yield is 67.2 percent;
the obtained white solid BYLC-01 was analyzed by GC-MS and the M/z of the product was 342(M +).
1H-NMR(300MHz,CDCl3):0.15-0.85(m,5H), 2.85-4.65(m,2H),4.35-6.75(m,1H),6.85-7.35(m,3H)。
Example 2
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-02 was analyzed by GC-MS and the M/z of the product was 312(M +).
1H-NMR(300MHz,CDCl3):0.15-0.85(m,3H), 2.85-4.65(m,2H),4.35-6.75(m,1H),6.85-7.35(m,3H)。
Example 3
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-03 was analyzed by GC-MS and the M/z of the product was 342(M +).
1H-NMR(300MHz,CDCl3):0.15-0.85(m,5H), 2.85-4.65(m,2H),4.35-6.75(m,1H),6.85-7.35(m,3H)。
Example 4
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-04 was analyzed by GC-MS and the M/z of the product was 356(M +).
1H-NMR(300MHz,CDCl3):0.15-0.85(m,5H), 2.85-4.65(m,4H),4.35-6.75(m,1H),6.85-7.35(m,3H)。
Example 5
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-05 was analyzed by GC-MS and the M/z of the product was 328(M +).
1H-NMR(300MHz,CDCl3):0.15-0.85(m,3H), 2.85-4.65(m,2H),4.35-6.75(m,1H),6.85-7.35(m,3H)。
Example 6
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-06 was analyzed by GC-MS and the M/z of the product was 386(M +).
1H-NMR(300MHz,CDCl3):0.15-1.85(m,8H), 1.95-4.65(m,3H),5.35-6.75(m,2H),6.85-7.35(m,2H)。
Example 7
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-07 was analyzed by GC-MS and the M/z of the product was 356(M +).
1H-NMR(300MHz,CDCl3):0.15-1.85(m,6H), 1.95-4.65(m,3H),5.35-6.75(m,2H),6.85-7.35(m,2H)。
Example 8
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-08 was analyzed by GC-MS and the M/z of the product was 372(M +).
1H-NMR(300MHz,CDCl3):0.15-1.85(m,6H), 1.95-4.65(m,3H),5.35-6.75(m,2H),6.85-7.35(m,2H)。
Example 9
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-09 was analyzed by GC-MS and the M/z of the product was 354(M +).
1H-NMR(300MHz,CDCl3)：0.15-1.85(m,6H), 1.95-4.65(m,5H),5.35-6.75(m,2H),6.85-7.35(m,2H)。
Example 10
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-10 was analyzed by GC-MS and the M/z of the product was 368(M +).
1H-NMR(300MHz,CDCl3):0.15-1.85(m,6H), 1.95-4.65(m,7H),5.35-6.75(m,2H),6.85-7.35(m,2H)。
According to the technical scheme of the embodiment, the liquid crystal compound mentioned in the summary of the invention can be synthesized only by simply replacing the corresponding raw materials without changing any substantial operation.
Comparative example
Examples of the experiments
The data of the performance parameters of the compounds prepared in the examples were compared and the results are shown in table 1:
from the above experimental data, it can be seen that the liquid crystal compound provided by the present invention has a large vertical dielectric anisotropy, and the overall dielectric anisotropy is positive and is approximately 0.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (11)
1. A liquid crystal compound, characterized by being selected from one or more of the following compounds:
in the above formulae, Z represents a single bond, -O-, -CH2-、-CH2CH2-or-CH2O-；R2represents-CF3or-OCF3。
2. The liquid crystal compound of claim 1, wherein the compound is selected from the group consisting of I-1, I-2, and I-3.
3. The liquid crystal compound according to claim 1, wherein the compound is selected from one or more of the following compounds:
。
4. the liquid crystal compound according to claim 1, wherein the compound is selected from one or more of the following compounds:
。
5. a process for producing a liquid crystal compound according to any one of claims 1 to 4, which comprises:
1) will be provided with
Metalating with organic lithium reagent, and reacting with boric acid ester to obtain
；
2)
And
by suzuki reaction, obtaining
；
3)
Ring closure is carried out under the catalysis of alkali to obtain
。
6. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 4; the mass percentage of the compound in the composition is 0.01-60%.
7. The liquid crystal composition according to claim 6, wherein the compound is contained in the composition in an amount of 0.1 to 50% by mass.
8. The liquid crystal composition according to claim 7, wherein the compound is contained in the composition in an amount of 0.1 to 40% by mass.
9. Use of the liquid crystal compound according to any one of claims 1 to 4 or the liquid crystal composition according to any one of claims 6 to 8 in the field of liquid crystal displays.
10. Use according to claim 9, in a liquid crystal display device.
11. The use according to claim 10, wherein the liquid crystal display device is a VA, TN, STN, FFS or IPS liquid crystal display.
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| CN105153112A (en) * | 2014-04-22 | 2015-12-16 | 默克专利股份有限公司 | 4,6-difluoro dibenzothiophene derivates |
| CN106811209A (en) * | 2015-11-30 | 2017-06-09 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds, composition and its application |
| CN106811208A (en) * | 2015-11-30 | 2017-06-09 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds, composition and its application |
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