CN102795974A - Liquid crystal medium and liquid crystal composition - Google Patents
Liquid crystal medium and liquid crystal composition Download PDFInfo
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- CN102795974A CN102795974A CN2012102698983A CN201210269898A CN102795974A CN 102795974 A CN102795974 A CN 102795974A CN 2012102698983 A CN2012102698983 A CN 2012102698983A CN 201210269898 A CN201210269898 A CN 201210269898A CN 102795974 A CN102795974 A CN 102795974A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 3
- 210000002858 crystal cell Anatomy 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 0 CC*C1=CC(CC(*)C2)C2C=C1 Chemical compound CC*C1=CC(CC(*)C2)C2C=C1 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides compounds having a general formula (I), used as a component of a liquid crystal medium and having an indene ring structure as well as a preparation method and application of the compounds. The compounds are negative liquid crystal compounds, and have the advantages of high dielectric and anisotropic absolute value, proper optical anisotropy, high clearing point and wide nematic phase temperature range; and a display using the compounds can have high response speed and wide working range, and can be well displayed in various environments. The invention also provides a liquid crystal composition comprising one or more of the compounds and a liquid crystal element comprising the liquid crystal composition.
Description
Technical Field
The invention relates to a compound containing an indene ring structure as a component of a negative liquid crystal medium, and a preparation method and application thereof
Background
Liquid crystal display devices are classified into types such as PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), and the like, according to a display mode of liquid crystal. The driving method of the element is classified into a PM (passive matrix) type and an AM (active matrix) type. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into a TFT (thin film transistor), an MIM (metal insulator metal), and the like. The types of TFTs are amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to a manufacturing process. Liquid crystal display elements are classified into a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both light sources of natural light and backlight, depending on the type of light source.
The most common of these effects are the TN effect, the STN effect and the SBE (super twisted birefringence) effect. In both these and similar electro-optical effects, liquid crystal media of positive dielectric anisotropy are used. In addition to the mentioned electro-optical effects using liquid-crystalline media of positive dielectric anisotropy, there are also other electro-optical effects which make use of liquid-crystalline media of negative dielectric anisotropy, such as the ECB (electrically controlled birefringence) effect and its sub-form DAP (phase alignment deformation) effect, the VAN effect and the CSH (color super homeotropic) effect.
The liquid crystal material must have good chemical and thermal stability and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid crystal material should have low viscosity and short response time, low threshold voltage and high contrast. While the optical anisotropy of the composition correlates with the contrast of the element.
In recent years, in a large-sized liquid crystal television, a Thin Film Transistor (TFT) display mode in which liquid crystal molecules are Vertically Aligned (VA) is widely used. Its advantages are wide visual angle, high response speed and high contrast. A conventional twisted-nematic mode (TN) uses a liquid crystal material having a positive dielectric anisotropy (Δ ∈ ═ epsilon/epsilon ∈, Δ ∈ > 0) with a polar group in the molecular long axis direction so that the long axis direction dielectric constant (epsilon /) is larger than the short axis direction dielectric constant (epsilon ∈); the VA mode requires a liquid crystal material having a large negative dielectric anisotropy (Δ ∈ < 0) and a large optical anisotropy (Δ n).
In liquid crystal displays, it is required that the operating voltage of the display should be as low as possible, and liquid crystal media having large absolute values of dielectric anisotropy are required.
In order to ensure satisfactory quality, particularly low-voltage characteristics, in VA-TFT displays, substances having a large absolute value of dielectric anisotropy, appropriate optical anisotropy, low viscosity, a wide operating temperature range, high response speed, good chemical stability, good uv stability, and good miscibility are required.
It is known that anisotropic liquid crystal compounds, in particular liquid crystal materials of negative dielectric anisotropy, whose compound molecules mostly consist of aromatic rings substituted in the 2, 3 position by halogen, trifluoromethyl or cyano, where necessary covalently bonded to each other, contain one or more lateral groups in the molecule, usually cyano or nitro.
Such liquid-crystal compositions of negative dielectric anisotropy are described in German patents DE2240864, DE2613293 and DE2835662, which have a negative dielectric anisotropy (. DELTA.. di-elect cons.).
A negative dielectric anisotropy liquid crystal compound represented by the following formula is described in Chinese patent CN1454890
However, these negative liquid crystal materials have a weak negative dielectric anisotropy.
The development in the field of liquid crystal materials is still far and still, and in order to improve the properties of liquid crystal elements, efforts are still required to develop novel compounds capable of optimizing liquid crystal displays.
It is therefore an object of the present invention to provide compounds for liquid-crystalline media which have excellent properties. The compound has negative dielectric anisotropy, is particularly suitable for a VA display mode, and can meet the requirements of a liquid crystal element on large absolute value of dielectric anisotropy, proper optical anisotropy, low viscosity, wide working temperature range, high response speed, good chemical stability, good ultraviolet light stability, good intersolubility and the like.
Disclosure of Invention
The invention aims to provide a compound containing an indene structure, which can be used as a component of a liquid crystal medium and can be used as a negative liquid crystal material.
Another object of the present invention is to provide a process for preparing the above compounds containing an indene ring structure.
It is still another object of the present invention to provide a liquid crystal composition comprising the compound having an indene ring structure.
It is still another object of the present invention to provide a liquid crystal cell comprising the liquid crystal composition as a constituent element.
In one aspect of the present invention, there is provided an indene ring structure-containing compound which can be used as a component of a liquid crystal medium, the compound having a structure represented by general formula (I):
wherein,
R1and R2The same or different, each independently represents H, halogen, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 15 carbon atoms or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 15 carbon atoms, wherein, in the R1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
ring (C)
Ring (C)
Are identical or different and are each independently of the others selected from A group of (a);
Z1and Z2Identical or different, each independently of the others, selected from the group consisting of a carbon-carbon single bond and-CO-O-, -O-CO-, -CF2O-、-CH2O-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH=CF-、-C2F4-and-C ≡ C-;
z is independently selected from the group consisting of-OCH2CH2O-、-(CH2)4-、-OCF2CF2A group consisting of O-and a combination of,
m and n are identical or different and are each independently of the other 0, 1 or 2; and m + n3 is more than or equal to 0.
In some embodiments, R1And R2Each independently represents H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 10 carbon atoms, wherein, in the R group1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other. Preferably, R1And R2Each independently represents an alkyl group of 1 to 5 carbon atoms.
In some embodiments, Z1And Z2Identical or different, each independently of the others, selected from the group consisting of-CO-O-, -O-CO-, -CF2O-、-CH2O-、-CH2CH2-、-CF2CH2-, -CF = CF-, -CH = CH-, -C ≡ C-, and a carbon-carbon single bond;
in some embodiments, Z is independently selected from the group consisting of-OCF2CF2O-, or-OCH2CH2O-;
in some embodiments, m and n are the same or different, each independently from the other selected from 0 or 1; and m + n is more than or equal to 0 and less than or equal to 2.
Preferably, the compounds of the invention are selected from the group consisting of:
wherein,
R1and R2Each independently represents H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 10 carbon atoms, wherein, in the R group1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
Another aspect of the invention provides a method of preparing a compound of the invention, comprising the steps of:
1) in the solvent tetrahydrofuran, in N2Under protection, the compound of the general formula 1
(general formula 1)
Reacting with magnesium powder to generate Grignard reagent of general formula 2
Dropwise adding triisobutyl borate into the reaction system at the temperature of between 30 ℃ below zero and 10 ℃ below zero, and stirring and reacting at room temperature for 0.5 to 4 hours after dropwise adding to obtain a compound of a general formula 3;
2) In a dichloromethane solvent, stirring and reacting the compound of the general formula 3 with 30% hydrogen peroxide for 2-8h at room temperature to obtain a compound of a general formula 4;
3) In tetrahydrofuran solvent, N at room temperature2Under protection, stirring and reacting the compound of the general formula 4, 2-chloroethanol, triphenylphosphine and diisopropyl azodicarboxylate for 1-16h to obtain a compound of a general formula 5;
4) In tetrahydrofuran solvent at-78 deg.C, N2Under protection, adding the compound of the general formula 6, n-butyllithium and triisobutyl borate, and after finishing the addition, at room temperature for 0.5-2h to obtain a compound of a general formula 7;
5) In a dichloromethane solvent, stirring and reacting the compound of the general formula 7 with 30% hydrogen peroxide for 1-14h at room temperature to obtain a compound of a general formula 8;
6) Stirring and reacting a compound of a general formula 5, a compound of a general formula 8, potassium carbonate, potassium iodide and N, N-methylformamide for 0.5-8h at the temperature of 80-100 ℃ to obtain a compound of a general formula I;
wherein R is1、R2Ring of
Ring (C)
Z1、Z2Z and m and n have the same meanings as defined above.
Another aspect of the invention provides a liquid crystal composition comprising one or more compounds of the invention.
Still another aspect of the present invention provides a liquid crystal cell comprising the liquid crystal composition.
Compared with other liquid crystal compounds in the prior art, the liquid crystal compound shown in the general formula (I) provided by the invention has large absolute value (delta epsilon) of dielectric anisotropy, large optical anisotropy (delta n) and low rotational viscosity (gamma)1) High clearing point (Cp) and wide nematic phase temperature range, which are chemically stable; in the preparation process of the general formula (I), the raw materials are easy to obtain, the synthetic route is simple and feasible, the method is suitable for large-scale industrial production, is favorable for being used as a liquid crystal material for display, and can be usedTo improve the response time (i.e., reduce the rotational viscosity) of the liquid crystal composition; the damage resistance to light and heat is improved; the working temperature range is expanded.
Drawings
Fig. 1 is a mass spectrum of compound 3IO2OWO 2.
Fig. 2 is a nuclear magnetic spectrum of compound 3IO2OWO 2.
Fig. 3 is a mass spectrum of compound 2IO2OWO 2.
Fig. 4 is a nuclear magnetic spectrum of compound 2IO2OWO 2.
Fig. 5 is a mass spectrum of compound 3IO2OWP 3.
Fig. 6 is a nuclear magnetic spectrum of compound 3IO2OWP 3.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
The shorthand codes of the test items in the following examples are respectively expressed as:
cp (. degree. C.) clearing Point (nematic-isotropic phase transition temperature)
Δ n optical anisotropy (589 nm, 20 ℃ C.)
Delta epsilon dielectric anisotropy (1 KHz, 25 ℃ C.)
Wherein the refractive index anisotropy is measured by using an Abbe refractometer under a sodium lamp (589 nm) light source at 20 ℃; the dielectric test cell was of the type TN90, the cell thickness being 7 μm.
The reagents and other starting materials used in the present invention are commercially available.
For convenience of expression, the following liquid crystal compounds are represented by the codes listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Take the following structure as an example:
the structure is represented by the code in table 1: it may be denoted as 3PTWTP3, again as:
it can be expressed as nCPTPOm, where n in the code represents the number of C atoms of the left alkyl group, e.g., n is "3", i.e., the alkyl group is-C3H7(ii) a C in the code represents cyclohexane; o in the code represents an oxygen atom; p in the code represents phenylene; in the code, m represents the number of C atoms in the alkyl group at the right end, for example, m is "1", that is, the alkyl group at the right end is-CH3。
Monomer extrapolation test method:
the monomer was mixed with the mother liquid crystal composition (DELTA n: 0.126; DELTA ε: -5.5; Cp: 82.1 ℃) in a weight ratio of 1:9, and then the properties of the monomer were calculated in accordance with the linearity.
Example 1
The synthetic route for compound 3IO2OWO2 prepared is shown below:
the specific process steps are as follows:
1) synthesis of 3IO2OWO2-2
A500 mL three-necked flask was charged with 5.76g of Mg powder and 0.05g of iodine, 10mL of Tetrahydrofuran (THF), under nitrogen. Dissolving 47.6g of 3IO2OWO2-1 compound in 200mL of tetrahydrofuran solution, slowly adding the tetrahydrofuran solution of the 3IO2OWO2-1 (commercial intermediate) compound into the reaction system, continuously dropwise adding the remaining tetrahydrofuran solution of the 3IO2OWO2-1 compound after the reaction is initiated, keeping the system slightly boiling and refluxing for 3h after the dropwise adding is finished, cooling to room temperature, cooling to-30 ℃, controlling the temperature to be minus 30 ℃ to minus 10 ℃, slowly dropwise adding 92g of triisobutyl borate, and stirring at room temperature for 0.5-4 h. The reaction solution is quenched by dilute hydrochloric acid, extracted by ethyl acetate, the organic phase is dried by anhydrous sodium sulfate, the solvent is dried by spinning, and the white solid 33g with the yield of 80 percent is the compound of 3IO2OWO2-2 after petroleum ether crystallization. MS: m/z: 204.
2) Synthesis of 3IO2OWO2-3
20.4g of 3IO2OWO2-2 compound, 100mL of dichloromethane and 30mL of 30% hydrogen peroxide are added into a 250mL round bottom flask, and the mixture is stirred at room temperature and reacts for 2 to 8 hours. The dichloromethane solvent was evaporated, 100mL of water was added, suction filtered and dried to obtain 17g of a white solid, yield 96.6%, which was a 3 compound. MS: m/z: 176.
3) Synthesis of 3IO2OWO2-4
A250 mL round-bottom flask was charged with 8.8g of 3IO2OWO2-3 compound, 4.1g of 2-chloroethanol, 13.5g of triphenylphosphine, 11g of diisopropyl azodicarboxylate, and 100mL of tetrahydrofuran, and the reaction was stirred at room temperature for 1-16h under nitrogen. Adding 100mL of water into the reaction solution, extracting with ethyl acetate, spin-drying the organic solvent, performing column chromatography by using petroleum ether as a mobile phase, and concentrating the eluent to obtain 10g of a colorless transparent oily substance which is a compound of 3IO2OWO 2-4. MS: m/z: 238.
4) Synthesis of 3IO2OWO2-6
A100 mL round-bottom flask was charged with 7.5g of 3IO2OWO2-5 (a commercially available intermediate), 30mL THF, nitrogen blanketed, and 13mL n-butyllithium (n-BuLi, 2.4 mol/L) was added dropwise at-78 deg.C for 0.5-2 h. Dissolving 14g of triisobutyl borate in 20mL of THF, dripping into a reaction system at-78 ℃, naturally raising the temperature to room temperature after dripping, and stirring for reaction for 0.5-2 h. And (3) pouring the reaction liquid into dilute hydrochloric acid to quench the reaction, stirring for 30min, extracting with ethyl acetate, spin-drying the organic solvent, washing the residue with petroleum ether, and performing suction filtration to obtain 5g of white solid, namely a compound of 3IO2OWO 2-6.
5) Synthesis of 3IO2OWO2-7
5g of 3IO2OWO2-6 compound, 30mL of dichloromethane and 5mL of 30% hydrogen peroxide are added into a 100mL round bottom flask, and the mixture is stirred at room temperature and reacts for 1-14 h. The dichloromethane solvent was evaporated, 50mL water was added, suction filtered and dried to give 4.5g of a white solid, 3IO2OWO 2-7. MS: m/z: 174.
6) Synthesis of 3IO2OWO2
1g of 3IO2OWO2-4 compound, 0.73g of 3IO2OWO2-7 compound, 1.16g of potassium carbonate, 0.07g of potassium iodide and 10mL of N, N-dimethylformamide are added into a 50mL round-bottom flask, and the mixture is stirred and reacted for 0.5-8h at the temperature of 80-100 ℃. Adding 50mL of water into the reaction solution, extracting with ethyl acetate, spin-drying the organic solvent, separating by using petroleum ether as a mobile phase column chromatography, concentrating the eluent to obtain 1.2g of white solid, and recrystallizing with absolute ethyl alcohol to obtain 1g of white needle-shaped crystals with the purity of 99.5%. To obtain a compound 8. MS m/z 376.1H-NMR（300MHz，CDCl3）：7.086（1H，d）；6.787-6.719（1H，m）；6.698-6.559（3H，m）；4.351-4.256（4H，m）；4.103-4.003（2H，m）；3.030-2.931（2H，m）；2.585-2.493（2H，m）；2.675-2.483（3H，m）；1.579-1.351（7H，m）；0.962-0.915（3H，t）。
The mass spectrum and nuclear magnetic spectrum are shown in fig. 1 and 2, respectively.
Liquid crystal properties of compound 3IO2OWO 2:
Δn：0.056 Δε：-9.5 Cp：15.7
example 2
2IO2OWO2 was synthesized in the same manner as described above.
The mass spectrum and nuclear magnetic spectrum are shown in fig. 3 and 4, respectively.
Liquid crystal performance:
Δn：0.069 Δε：-9.5 Cp：5.6
example 3
The synthetic route for compound 3IO2OWP3 prepared is shown below:
the specific process steps are as follows:
1) 3IO2OWP3-2, 3IO2OWP3-3 and 3IO2OWP3-4 refer to the synthesis methods of 2IO2OWO2-2, 2IO2OWO2-3 and 2IO2OWO2-4, and the compound 3IO2OWP3-1 shown in the synthesis scheme is a commercially available intermediate.
2) Synthesis of 3IO2OWP3-10
A100 mL round-bottomed flask was charged with 19.2g of 3IO2OWP3-9 (a commercially available intermediate), 30mL of THF, nitrogen blanketed, and 50mL of n-butyllithium (n-BuLi, 2.4 mol/L) were added dropwise at a temperature of-78 ℃ to complete the reaction for 2 hours. 46g of triisobutyl borate is dissolved in 20mL of THF, the solution is dripped into a reaction system at-78 ℃, the temperature is naturally raised to room temperature after dripping, and the reaction is stirred for 2 hours. And (3) pouring the reaction liquid into dilute hydrochloric acid to quench the reaction, stirring for 30min, extracting with ethyl acetate, spin-drying the organic solvent, washing the residue with petroleum ether, and performing suction filtration to obtain 8g of white solid, namely a compound of 3IO2OWP 3-10.
3) Synthesis of 3IO2OWP3-12
A250 mL round-bottomed flask was charged with 9.3g of the compound 3IO2OWP3-10, 11.7g of the compound 3IO2OWP3-11 (commercially available intermediate), 100mL of ethylene glycol dimethyl ether, and 35mL of an aqueous potassium carbonate solution (2 mol. L)-1) 0.5g of tetrabutylammonium bromide, 0.4g of Pd (PPh)3)4And carrying out reflux reaction for 5 hours under the protection of nitrogen. Quenching the reaction with water, extracting with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, spin-drying the solvent, separating with petroleum ether as mobile phase column chromatography, and concentrating the eluate to obtain colorless liquid 8.4g, to obtain 3IO2OWP3-12 compound. MS: m/z: 232.
4) Synthesis of 3IO2OWP3-13
4.64g of 3IO2OWP3-12 compound, 50mL of THF and nitrogen protection are added into a 250mL three-neck flask, 10mL of n-BuLi (2.4 mol/L) n-hexane solution is dripped into the flask at the temperature of-78 ℃ and the reaction is finished for 2h after dripping. 4.6g of triisobutyl borate is dissolved in 10ml of THF, and the solution is dripped into the reaction system at-78 ℃ and stirred for 2 hours after dripping. Pouring the reaction liquid into dilute hydrochloric acid-ice-water, stirring for 30min, extracting with ethyl acetate, spin-drying the organic phase, washing the residue with petroleum ether, and performing suction filtration to obtain 3g of white solid, thereby obtaining the compound of 3IO2OWP 3-13.
5) Synthesis of 3IO2OWP3-14
13.8g of the compound 3IO2OWP3-13, 150mL of dichloromethane and 30mL of 30% hydrogen peroxide are added into a 100mL round-bottom flask, and the mixture is stirred and reacted for 4 hours at room temperature. The dichloromethane solvent was evaporated, 100mL water was added, suction filtered and dried to give 10.1g of a white solid, 3IO2OWP 3-14. MS: m/z: 248.
6) Synthesis of 3IO2OWP3
1g of 3IO2OWP3-4 compound, 1g of 3IO2OWP3-14 compound, 1.16g of potassium carbonate, 0.07g of potassium iodide and 10mLN, N-dimethylformamide are added into a 50mL round-bottom flask, and the mixture is stirred and reacted for 0.5-8h at the temperature of 80-100 ℃. Adding 50mL of water into the reaction solution, extracting with ethyl acetate, spin-drying the organic solvent, separating by column chromatography with petroleum ether as a mobile phase, concentrating the eluent to obtain 1.1g of white solid, and recrystallizing with anhydrous ethanol to obtain 0.88g of white needle crystal with purity of 99.79%. Compound 3IO2OWP3 was obtained. MS: m/z: 450.1H-NMR（300MHz，CDCl3）：7.439-7.407（2H，m）；7.266-7.239（2H，t）；7.106-7.066（2H，m）；6.896（1H，d）；6.801（1H，s）；6.741-6.706（1H，m）；4.445-4.413（2H，m）；4.349-4.341（2H，m）；2.982-2.956（2H，m）；2.658-2.607（2H，m）；2.515-2.474（3H，m）；1.723-1.648（2H，m）；1.552-1.371（4H，m）；1.003-0.911（6H，m）。
The mass spectrum and nuclear magnetic spectrum are shown in fig. 5 and 6, respectively.
Liquid crystal properties of compound 3IO2OWP 3:
Δn：0.156 Δε：-6.5 Cp：44.4
example 4
The properties of monomers 2PO2OWO2 and 2IO2OWO2, measured after dissolving them in the above-described mother liquid crystal composition (. DELTA.n: 0.126;. DELTA.. di-elect cons.: 5.5; Cp: 82.1 ℃ C.), were extrapolated to the monomer property parameters as shown in Table 2 below:
TABLE 2 liquid crystal monomer Structure and its test Performance
Example 5
The properties of the monomers 3CO2OWO2 and 3IO2OWO2 measured after dissolving in the above-described mother liquid crystal composition (Δ n: 0.126; Δ ε: -5.5; Cp: 82.1 ℃) were extrapolated to monomer property parameters as shown in Table 3 below:
TABLE 3 liquid crystal monomer Structure and its test Performance
As can be seen from the table data of example 4 and example 5, the compounds provided by the present invention have a large dielectric anisotropy, a good optical anisotropy and a suitably high clearing point as compared with the same type of compounds. The liquid crystal compound can ensure that a liquid crystal display applying the compound has excellent power-saving performance and higher response speed, can expand the working range of the liquid crystal display and can keep good display in various environments.
Claims (10)
1. A compound having the general formula (I):
wherein,
R1and R2Identical or different, each independently of the others, represents H, halogen, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 15 carbon atoms or a halogenated or unsubstituted alkanyl group having 2 to 15 carbon atoms orAlkoxyalkenyl, wherein in said R1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
ring (C)
Ring (C)
Are identical or different and are each independently of the others selected from 
A group of (a);
Z1and Z2Identical or different, each independently of the others, selected from the group consisting of a carbon-carbon single bond and-CO-O-, -O-CO-, -CF2O-、-CH2O-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH=CF-、-C2F4-and-C ≡ C-;
z is independently selected from the group consisting of-OCH2CH2O-、-(CH2)4-、-OCF2CF2A group consisting of O-and a combination of,
m and n are identical or different and are each independently of the other 0, 1 or 2; and m + n is more than or equal to 0 and less than or equal to 3.
2. A compound of claim 1, wherein R is1And R2Each independently represents H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 10 carbon atoms, whereinR1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
3. The compound of claim 1, wherein Z is1And Z2Identical or different, each independently of the others, selected from the group consisting of-CO-O-, -O-CO-, -CF2O-、-CH2O-、-CH2CH2-、-CF2CH2-, -CF = CF-, -CH = CH-, -C ≡ C-and carbon-carbon single bonds.
4. The compound of claim 1, wherein Z is independently selected from the group consisting of-OCF2CF2O-or-OCH2CH2O-。
5. A compound according to claim 1, wherein m and n, which are the same or different, are each independently selected from 0 or 1; and m + n is more than or equal to 0 and less than or equal to 2.
6. The compound according to claims 1-5, selected from the group consisting of:
wherein,
R1and R2Each independently represents H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 10 carbon atoms, wherein, in the R group1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atom is not directly replacedAre connected to each other.
7. The compound according to claims 1-5, selected from the group consisting of:
8. a process for the preparation of a compound as claimed in any one of claims 1 to 7, comprising the steps of:
1) in the solvent tetrahydrofuran, in N2Under protection, the compound of the general formula 1
Reacting with magnesium powder to generate Grignard reagent of general formula 2
Dropwise adding triisobutyl borate into the reaction system at the temperature of between 30 ℃ below zero and 10 ℃ below zero, and stirring and reacting at room temperature for 0.5 to 4 hours after dropwise adding to obtain a compound of a general formula 3;
2) In a dichloromethane solvent, stirring and reacting the compound of the general formula 3 with 30% hydrogen peroxide for 2-8h at room temperature to obtain a compound of a general formula 4;
3) In tetrahydrofuran solvent, N at room temperature2Under protection, stirring and reacting the compound of the general formula 4, 2-chloroethanol, triphenylphosphine and diisopropyl azodicarboxylate for 1-16h to obtain a compound of a general formula 5;
4) In tetrahydrofuran solvent at-78 deg.C, N2Under protection, adding the compound of the general formula 6, n-butyllithium and triisobutyl borate, and after finishing the addition, at room temperature for 0.5-2h to obtain a compound of a general formula 7;
(general formula 6)
(general formula 7)
5) In a dichloromethane solvent, stirring and reacting the compound of the general formula 7 with 30% hydrogen peroxide for 1-14h at room temperature to obtain a compound of a general formula 8;
6) Stirring and reacting a compound of a general formula 5, a compound of a general formula 8, potassium carbonate, potassium iodide and N, N-methylformamide for 0.5-8h at the temperature of 80-100 ℃ to obtain a compound of a general formula I;
9. a liquid crystal composition comprising one or more compounds of any one of claims 1 to 8.
10. A liquid crystal cell comprising the liquid crystal composition of claim 9.
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