CN102795974B - Liquid crystal medium and liquid crystal composition - Google Patents
Liquid crystal medium and liquid crystal composition Download PDFInfo
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- CN102795974B CN102795974B CN201210269898.3A CN201210269898A CN102795974B CN 102795974 B CN102795974 B CN 102795974B CN 201210269898 A CN201210269898 A CN 201210269898A CN 102795974 B CN102795974 B CN 102795974B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 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 27
- 238000003756 stirring Methods 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 13
- 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 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004327 boric acid Substances 0.000 claims description 8
- -1 isobutyl ester Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 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
- 210000002858 crystal cell Anatomy 0.000 claims description 5
- 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
- 238000000034 method Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- 235000007715 potassium iodide Nutrition 0.000 claims description 4
- 229960004839 potassium iodide Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 claims description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 230000003287 optical effect Effects 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 0 *C(C1)CC2=C1CCC(*)=C2 Chemical compound *C(C1)CC2=C1CCC(*)=C2 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-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
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 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
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010189 synthetic 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
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 present invention relates to compound containing indenes ring structure of the component as negative liquid crystal medium and its preparation method and application
Background technology
For liquid crystal display device, PC(phase change is divided into according to the display format of liquid crystal, phase transformation), TN(twistnematic, twisted-nematic), STN (super twisted nematic, supertwist to row), ECB(electrically controlledbirefringence, electrically conerolled birefringence), OCB(optically compensated bend, optical compensation curved), IPS(in-planeswitching, coplanar transformation), VA(vertical alignment, vertical orientation) etc. type.PM(passive matrix is divided into, passive-matrix according to the type of drive of element) type and AM(active matrix, active-matrix) type.PM is divided into the type such as static state (static) and multichannel (multiplex).AM is divided into TFT(thin film transistor, thin film transistor), MIM(metal insulator metal, metal-insulator-metal) etc. type.The type of TFT has non-crystalline silicon (amorphous silicon) and polysilicon (polycrystal silicon).The latter is divided into high temperature modification and low temperature modification according to manufacturing process.Liquid crystal display device is divided into according to the type of light source and utilizes the reflection-type of natural light, utilizes the infiltration type of backlight and utilize the semi-transmission type of natural light and backlight two kinds of light sources.
The most generally TN effect is applied, STN effect and SBE(SBE in these effects) effect.In the electrooptic effect that these electrooptic effects are similar with it, all use the liquid crystal media of positive dielectric anisotropy.Except the electrooptic effect of the liquid crystal media of the positive dielectric anisotropy of the use mentioned, also has other the electrooptic effect utilizing the liquid crystal media of negative dielectric anisotropic, such as ECB(electrically conerolled birefringence) effect and its sub-form DAP(join be out of shape in opposite directions) effect, VAN effect and the colored super vertical plane of CSH() effect.
Liquid crystal material must have good chemistry and thermostability and the good stability to electric field and electromagnetic radiation.In addition, liquid crystal material should have low viscosity and short response time, low threshold voltage and high-contrast.And the optical anisotropy of composition is associated with the contrast gradient of element.
In recent years in large-size liquid crystal television, thin film transistor (TFT) display format of liquid crystal molecule (VA) arranged vertically is used widely.Its advantage is that visual angle is wide, fast response time, contrast gradient are larger.Traditional distortion-nematic-mode (TN) uses dielectric anisotropy to be just (Δ ε=ε ∥-ε ⊥, Δ ε > 0) liquid crystal material, molecular long axis direction has polar group, makes long axis direction specific inductivity (ε ∥) be greater than perpendicular electric constant (ε ⊥); And the liquid crystal material that VA pattern requirements adopts has the larger dielectric anisotropy of negativity value (Δ ε <0) and larger optical anisotropy (Δ n).
In a liquid crystal display, require that the operating voltage of indicating meter should be low as much as possible, thus need the liquid crystal media with large dielectric anisotropy absolute value.
In order to ensure satisfied quality, the particularly characteristic of low voltage, in VA-TFT indicating meter, need to there is large dielectric anisotropy absolute value, suitable optical anisotropy, low viscosity, wide operating temperature range, high response speed, good chemical stability, the material of good ultraviolet light stability and good mutual solubility.
As everyone knows, the liquid crystal material of anisotropic liquid crystal compound particularly negative dielectric anisotropic, its compound molecule is most to be formed by the aromatic nucleus that halogen, trifluoromethyl or cyano group replace by 2,3, be connected with covalent linkage between aromatic ring when needed, containing one or more side direction groups in general formula molecule, these side direction groups normally cyano group or nitro.
In German patent DE 2240864, DE2613293 and DE2835662, relate to the liquid-crystal composition of this type of negative dielectric anisotropic, they have negative dielectric anisotropy (Δ ε).
The negative dielectric anisotropic liquid crystal compound be expressed from the next is described in Chinese patent CN1454890
But the liquid crystal material of these negativity has very weak negative dielectric anisotropic.
The research and development in liquid crystal material field still shoulder heavy responsibilities, and in order to improve the character of liquid crystal cell, exploitation that efforts still need to be can optimize the novel cpd of liquid-crystal display.
Therefore, the object of the present invention is to provide there is the compound of premium properties for liquid crystal media.This compound has negative dielectric anisotropic, be particularly suitable in VA display format, liquid crystal cell can be met to large dielectric anisotropy absolute value, suitable optical anisotropy, low viscosity, wide operating temperature range, high response speed, good chemical stability, the requirements such as good ultraviolet light stability and good mutual solubility.
Summary of the invention
The object of this invention is to provide a kind of can as the component of liquid crystal media containing the compound of indenes ring structure, this compound can as negative liquid crystal material.
Another object of the present invention is to provide the preparation method of the above-mentioned compound containing indenes ring structure.
Another object of the present invention is to provide a kind of liquid-crystal composition comprising the described compound containing indenes ring structure.
Another object of the present invention is to provide and a kind ofly comprises the liquid crystal cell of described liquid-crystal composition as integrant.
One aspect of the present invention, provide a kind of can as the component of liquid crystal media containing the compound of indenes ring structure, this compound has the structure shown in logical formula I:
Wherein,
R
1and R
2identical or different, independently represent H, halogen separately, there is the halo of 1-15 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-15 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other;
Ring
ring
identical or different, be independently from each other separately
the group of composition;
Z
1and Z
2identical or different, be independently from each other separately by carbon-carbon single bond and-CO-O-,-O-CO-,-CF
2o-,-CH
2o-,-CH
2cH
2-,-CF
2cH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2f
4-and-C ≡ C-form group;
Z is independently selected from by-OCH
2cH
2o-,-(CH
2)
4-,-OCF
2cF
2the group of O-composition,
M and n is identical or different, is independently from each other 0,1 or 2 separately; And 0≤m+n3.
In some embodiments, R
1and R
2independently represent H, F separately, there is the halo of 1-10 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-10 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other.Preferably, R
1and R
2represent the alkyl of 1-5 carbon atom independently of one another.
In some embodiments, Z
1and Z
2identical or different, be independently from each other separately by-CO-O-,-O-CO-,-CF
2o-,-CH
2o-,-CH
2cH
2-,-CF
2cH
2-,-CF=CF-,-CH=CH-,-C ≡ C-and carbon-carbon single bond composition group;
In some embodiments, Z is independently selected from by-OCF
2cF
2o-or-OCH
2cH
2the group of O-composition;
In some embodiments, m and n is identical or different, is independently from each other 0 or 1 separately; And 0≤m+n≤2.
Preferably, compound of the present invention is selected from the group be made up of following compound:
Wherein,
R
1and R
2independently represent H, F separately, there is the halo of 1-10 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-10 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other.
Another aspect of the present invention provides a kind of method preparing compound of the present invention, comprises the steps:
1) in solvents tetrahydrofurane, at N
2under protection, by the compound of general formula 1
(general formula 1)
React with magnesium powder, generate the Grignard reagent of general formula 2
(general formula 2)
At-30 DEG C--10 DEG C, drip boric acid three isobutyl ester to above-mentioned reaction system, dropwise stirring at room temperature reaction 0.5-4h, obtain the compound of general formula 3;
(general formula 3)
2) in dichloromethane solvent, under room temperature, by the compound of general formula 3 and 30% hydrogen peroxide, stirring reaction 2-8h, obtains the compound of general formula 4;
(general formula 4)
3) in tetrahydrofuran solvent, at room temperature, N
2under protection, by the compound of general formula 4, ethylene chlorhydrin, triphenylphosphine, diisopropyl azodiformate, stirring reaction 1-16h, obtains the compound of general formula 5;
(general formula 5)
4) in tetrahydrofuran solvent, at-78 DEG C, N
2under protection, add the compound of general formula 6, n-Butyl Lithium, boric acid three isobutyl ester, reinforced complete, under room temperature, 0.5-2h, obtains the compound of general formula 7;
(general formula 6)
(general formula 7)
5) in dichloromethane solvent, under room temperature, by the compound of general formula 7 and 30% hydrogen peroxide, stirring reaction 1-14h, obtains the compound of general formula 8;
(general formula 8)
6) at 80 DEG C-100 DEG C, the compound of general formula 5, the compound of general formula 8, salt of wormwood, potassiumiodide, N, N-METHYLFORMAMIDE, stirring reaction 0.5-8h, obtains the compound of formula I;
Wherein, R
1, R
2, ring
ring
z
1, Z
2, Z and m have and aforementioned identical definition with n.
Another aspect of the present invention provides a kind of liquid-crystal composition, comprises one or more of compound of the present invention.
Another aspect of the present invention provides a kind of liquid crystal cell comprising described liquid-crystal composition.
Compared with other liquid crystalline cpds of liquid crystalline cpd and prior art shown in logical formula I provided by the invention, there is large dielectric anisotropy absolute value (Δ ε), very large optical anisotropy (Δ n), low rotary viscosity (γ
1), high clearing point (Cp) and wider nematic temperature range, their chemical property is all stable; In logical formula I preparation process, raw material is easy to get, and synthetic route is simple, is applicable to large-scale industrial and produces, be beneficial to and use as display liquid crystal material, can be used for the time of response (namely reducing rotary viscosity) of improving liquid-crystal composition; Promote the survivability to light, heat; Expand operating temperature range.
Accompanying drawing explanation
Fig. 1 is the mass spectrum of compound 3IO2OWO2.
Fig. 2 is the nuclear magnetic spectrogram of compound 3IO2OWO2.
Fig. 3 is the mass spectrum of compound 2IO2OWO2.
Fig. 4 is the nuclear magnetic spectrogram of compound 2IO2OWO2.
Fig. 5 is the mass spectrum of compound 3IO2OWP3.
Fig. 6 is the nuclear magnetic spectrogram of compound 3IO2OWP3.
Embodiment
Below with reference to specific embodiments, the present invention is described.It should be noted that, the following examples are example of the present invention, are only used for the present invention is described, and are not used for limiting the present invention.When not departing from purport of the present invention or scope, other combination and the various improvement in design of the present invention can be carried out.
In following examples, the code name of writing a Chinese character in simplified form of each test event is expressed as:
Cp (DEG C) clearing point (to row-isotropic phase transition temperature)
Δ n optical anisotropy (589nm, 20 DEG C)
Δ ε dielectric anisotropy (1KHz, 25 DEG C)
Wherein, refractive anisotrop use Abbe refractometer under sodium lamp (589nm) light source, 20 DEG C test; Measurement box is TN90 type, thick 7 μm of box.
Reagent used in the present invention and other raw materials are commercially available commercial materials.
For ease of expressing, the coded representation listed by unit structure table 1 of following liquid crystalline cpd:
The unit structure code of table 1 liquid crystalline cpd
For following structure:
Coded representation in this structure table 1: then can be expressed as 3PTWTP3, and for example:
Then can be expressed as nCPTPOm, the n in code represents the C atomicity of left end alkyl, and such as n is " 3 ", namely represents that this alkyl is-C
3h
7; C in code represents cyclohexyl; O represention oxygen atom in code; P in code represents phenylene; M in code represents the C atomicity of right-hand member alkyl, and such as m is " 1 ", namely represents that the alkyl of right-hand member is-CH
3.
Monomer extrapolation measure method:
By monomer and parent liquid-crystal composition (Δ n:0.126; Δ ε :-5.5; Cp:82.1 DEG C) according to after weight ratio 1:9 mixing, carry out performance test, then calculate the properties of monomer according to linear gauge.
Embodiment 1
The synthetic route of the compound 3IO2OWO2 of preparation represents as follows:
Its concrete technology step is as follows:
1) synthesis of 3IO2OWO2-2
Mg powder and the 0.05g iodine of 5.76g is added, 10mL tetrahydrofuran (THF) (THF), nitrogen protection in 500mL there-necked flask.By the compound dissolution of the 3IO2OWO2-1 of 47.6g in 200mL tetrahydrofuran solution, slowly by commercially available for 3IO2OWO2-1(intermediate) the tetrahydrofuran solution of compound add to above-mentioned reaction system, after question response causes, continue the tetrahydrofuran solution of the compound dripping remaining 3IO2OWO2-1, drip and finish, the micro-backflow 3h that boils of maintenance system, be cooled to room temperature, be cooled to-30 DEG C, control temperature, at-30 DEG C ~-10 DEG C, slowly drips boric acid three isobutyl ester 92g stirring at room temperature 0.5-4h.Reaction solution dilute hydrochloric acid cancellation, extraction into ethyl acetate, organic phase anhydrous sodium sulfate drying, is spin-dried for solvent, and obtain white solid 33g after sherwood oil crystallization, yield 80% is the compound of 3IO2OWO2-2.MS:m/z:204。
2) synthesis of 3IO2OWO2-3
The compound of 20.4g3IO2OWO2-2 is added, 100mL methylene dichloride, 30mL30% hydrogen peroxide, stirring at room temperature reaction 2-8h in 250mL round-bottomed flask.Steam except dichloromethane solvent, adding 100mL water, suction filtration, after oven dry, obtain white solid 17g, yield 96.6%, is the compound of 3.MS:m/z:176。
3) synthesis of 3IO2OWO2-4
The compound of 8.8g3IO2OWO2-3,4.1g2-chloroethanol, 13.5g triphenylphosphine, 11g diisopropyl azodiformate, 100mL tetrahydrofuran (THF) is added in 250mL round-bottomed flask, under nitrogen protection, stirring at room temperature reaction 1-16h.Add 100mL water in reaction solution, extraction into ethyl acetate, be spin-dried for organic solvent, sherwood oil is moving phase pillar layer separation, and elutriant concentrates to obtain water white transparency oily thing 10g, is the compound of 3IO2OWO2-4.MS:m/z:238。
4) synthesis of 3IO2OWO2-6
Add the commercially available intermediate of 7.5g3IO2OWO2-5(in 100mL round-bottomed flask) compound, 30mL THF, nitrogen protection, low temperature, to the n-Butyl Lithium (n-BuLi, 2.4mol/L) instilling 13mL at-78 DEG C, drips Bi Fanying 0.5-2h.Boric acid three isobutyl ester of 14g is dissolved in 20mL THF, is added dropwise in reaction system in-78 DEG C, drip Bi Ziran and rise to room temperature, stirring reaction 0.5-2h.By cancellation reaction in reaction solution impouring dilute hydrochloric acid, stir 30min, extraction into ethyl acetate, is spin-dried for organic solvent, resistates petroleum ether, and suction filtration obtains white solid 5g, is the compound of 3IO2OWO2-6.
5) synthesis of 3IO2OWO2-7
The compound of 5g3IO2OWO2-6 is added, 30mL methylene dichloride, 5mL30% hydrogen peroxide, stirring at room temperature reaction 1-14h in 100mL round-bottomed flask.Steam except dichloromethane solvent, adding 50mL water, suction filtration, after oven dry, obtain white solid 4.5g, is the compound of 3IO2OWO2-7.MS:m/z:174。
6) synthesis of 3IO2OWO2
The compound of 1g3IO2OWO2-4, the compound of 0.73g3IO2OWO2-7,1.16g salt of wormwood, 0.07g potassiumiodide, 10mLN is added, dinethylformamide, 80 DEG C-100 DEG C stirring reaction 0.5-8h in 50mL round-bottomed flask.Add 50mL water in reaction solution, extraction into ethyl acetate, be spin-dried for organic solvent, sherwood oil is moving phase pillar layer separation, and elutriant concentrates to obtain white solid 1.2g, and dehydrated alcohol recrystallization, obtains white needle-like crystals 1g, purity 99.5%.Obtained compound 8.MS:m/z:376。
1H-NMR（300MHz，CDCl
3）：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）。
Mass spectrum and nuclear magnetic spectrogram show in fig. 1 and 2 respectively.
The liquid crystal property of compound 3IO2OWO2:
Δn：0.056 Δε：-9.5 Cp：15.7
Embodiment 2
Above-mentioned same method synthesis 2IO2OWO2.
Mass spectrum and nuclear magnetic spectrogram show in figs. 3 and 4 respectively.
Liquid crystal property:
Δn：0.069 Δε：-9.5 Cp：5.6
Embodiment 3
The synthetic route of the compound 3IO2OWP3 of preparation represents as follows:
Its concrete technology step is as follows:
1) 3IO2OWP3-2,3IO2OWP3-3,3IO2OWP3-4 can with reference to the synthetic methods of 2IO2OWO2-2,2IO2OWO2-3,2IO2OWO2-4, and the compound 3IO2OWP3-1 shown in synthetic route chart is commercially available intermediate.
2) synthesis of 3IO2OWP3-10
Add the commercially available intermediate of 19.2g3IO2OWP3-9(in 100mL round-bottomed flask) compound, 30mL THF, nitrogen protection, low temperature, to the n-Butyl Lithium (n-BuLi, 2.4mol/L) instilling 50mL at-78 DEG C, drips Bi Fanying 2h.Boric acid three isobutyl ester of 46g is dissolved in 20mL THF, is added dropwise in reaction system in-78 DEG C, drip Bi Ziran and rise to room temperature, stirring reaction 2h.By cancellation reaction in reaction solution impouring dilute hydrochloric acid, stir 30min, extraction into ethyl acetate, is spin-dried for organic solvent, resistates petroleum ether, and suction filtration obtains white solid 8g, is the compound of 3IO2OWP3-10.
3) synthesis of 3IO2OWP3-12
Add the compound of 9.3g3IO2OWP3-10, the commercially available intermediate of 11.7g3IO2OWP3-11(in 250mL round-bottomed flask) compound, 100mL glycol dimethyl ether, 35mL wet chemical (2molL
-1), 0.5g Tetrabutyl amonium bromide, 0.4g Pd (PPh
3)
4, nitrogen protection, back flow reaction 5h.Reaction shrend is gone out, extraction into ethyl acetate, and organic phase anhydrous sodium sulfate drying, is spin-dried for solvent, and sherwood oil is moving phase pillar layer separation, and elutriant concentrates to obtain colourless liquid 8.4g, the compound of obtained 3IO2OWP3-12.MS:m/z:232。
4) synthesis of 3IO2OWP3-13
Add the compound of 4.64g3IO2OWP3-12 in 250mL there-necked flask, 50mL THF, nitrogen protection, low temperature is to instilling 10mL n-BuLi(2.4mol/L at-78 DEG C) hexane solution, drip Bi Fanying 2h.Be dissolved in 10mLTHF by 4.6g boric acid three isobutyl ester ,-78 DEG C are added dropwise in reaction system, drip to finish to stir 2h.By in reaction solution impouring dilute hydrochloric acid-ice-water, stir 30min, extraction into ethyl acetate, is spin-dried for organic phase, resistates petroleum ether, and suction filtration obtains white solid 3g, the compound of obtained 3IO2OWP3-13.
5) synthesis of 3IO2OWP3-14
The compound of 13.8g3IO2OWP3-13 is added, 150mL methylene dichloride, 30mL30% hydrogen peroxide, stirring at room temperature reaction 4h in 100mL round-bottomed flask.Steam except dichloromethane solvent, adding 100mL water, suction filtration, after oven dry, obtain white solid 10.1g, is the compound of 3IO2OWP3-14.MS:m/z:248。
6) synthesis of 3IO2OWP3
The compound of 1g3IO2OWP3-4, the compound of 1g3IO2OWP3-14,1.16g salt of wormwood, 0.07g potassiumiodide, 10mLN is added, dinethylformamide, 80 DEG C-100 DEG C stirring reaction 0.5-8h in 50mL round-bottomed flask.Add 50mL water in reaction solution, extraction into ethyl acetate, be spin-dried for organic solvent, sherwood oil is moving phase pillar layer separation, and elutriant concentrates to obtain white solid 1.1g, and dehydrated alcohol recrystallization, obtains white needle-like crystals 0.88g, purity 99.79%.Obtained compound 3IO2OWP3.MS:m/z:450。
1H-NMR（300MHz，CDCl
3）：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）。
Mass spectrum and nuclear magnetic spectrogram show in fig. 5 and fig. respectively.
The liquid crystal property of compound 3IO2OWP3:
Δn：0.156 Δε：-6.5 Cp：44.4
Embodiment 4
Monomer 2PO2OWO2 and 2IO2OWO2 is dissolved in respectively above-mentioned parent liquid-crystal composition (Δ n:0.126; Δ ε :-5.5; Cp:82.1 DEG C) after the properties that records, obtain monomer performance perameter by extrapotation, as shown in table 2 below:
Table 2 liquid crystal monomer structure and test performance thereof
Embodiment 5
Monomer 3CO2OWO2 and 3IO2OWO2 is dissolved in above-mentioned parent liquid-crystal composition (Δ n:0.126; Δ ε :-5.5; Cp:82.1 DEG C) after the properties that records, obtain monomer performance perameter by extrapotation, as shown in table 3 below:
Table 3 liquid crystal monomer structure and test performance thereof
As can be seen from the list data of embodiment 4 and embodiment 5, compound provided by the invention and Compound Phase of the same type than having very large dielectric anisotropy, good optics anisotropic and suitably high clearing point.This type of liquid crystalline cpd can make the liquid-crystal display of this compound of application have superior power saving performance, and response speed faster can expand the working range of liquid-crystal display, makes liquid-crystal display all can keep good display in various environment.
Claims (10)
1. one kind has the compound of logical formula I:
Wherein,
R
1and R
2identical or different, independently represent H, halogen separately, there is the halo of 1-15 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-15 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other;
Ring
ring
identical or different, be independently from each other separately
the group of composition;
Z
1and Z
2identical or different, be independently from each other separately by carbon-carbon single bond and-CO-O-,-O-CO-,-CF
2o-,-CH
2o-,-CH
2cH
2-,-CF
2cH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2f
4-and-C ≡ C-form group;
Z is independently selected from by-OCH
2cH
2o-,-(CH
2)
4-,-OCF
2cF
2the group of O-composition,
M and n is identical or different, is independently from each other 0,1 or 2 separately; And 0≤m+n≤3.
2. compound according to claim 1, is characterized in that, described R
1and R
2independently represent H, F separately, there is the halo of 1-10 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-10 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other.
3. compound according to claim 1, is characterized in that, described Z
1and Z
2identical or different, be independently from each other separately by-CO-O-,-O-CO-,-CF
2o-,-CH
2o-,-CH
2cH
2-,-CF
2cH
2-,-CF=CF-,-CH=CH-,-C ≡ C-and carbon-carbon single bond composition group.
4. compound according to claim 1, is characterized in that, described Z is independently selected from by-OCF
2cF
2o-or-OCH
2cH
2o-.
5. compound according to claim 1, it is characterized in that, described m and n is identical or different, is independently from each other 0 or 1 separately; And 0≤m+n≤2.
6. compound according to claim 1-5, described compound is selected from the group be made up of following compound:
Wherein,
R
1and R
2independently represent H, F separately, there is the halo of 1-10 carbon atom or unsubstituted alkyl or alkoxyl group or there is the halo of 2-10 carbon atom or unsubstituted alkane thiazolinyl or alcoxyl thiazolinyl, wherein, at described R
1and R
2in one or more-CH
2-group can be substituted by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-independently of one another, and its prerequisite is that Sauerstoffatom is not directly connected to each other.
7. compound according to claim 1-5, described compound is selected from the group be made up of following compound:
8. prepare the method as the compound in claim 1 to 7 as described in any one, comprise the steps:
1) in solvents tetrahydrofurane, at N
2under protection, by the compound of general formula 1
React with magnesium powder, generate the Grignard reagent of general formula 2
At-30 DEG C--10 DEG C, drip boric acid three isobutyl ester to above-mentioned reaction system, dropwise stirring at room temperature reaction 0.5-4h, obtain the compound of general formula 3;
2) in dichloromethane solvent, under room temperature, by the compound of general formula 3 and 30% hydrogen peroxide, stirring reaction 2-8h, obtains the compound of general formula 4;
3) in tetrahydrofuran solvent, at room temperature, N
2under protection, by the compound of general formula 4, ethylene chlorhydrin, triphenylphosphine, diisopropyl azodiformate, stirring reaction 1-16h, obtains the compound of general formula 5;
4) in tetrahydrofuran solvent, at-78 DEG C, N
2under protection, add the compound of general formula 6, n-Butyl Lithium, boric acid three isobutyl ester, reinforced complete, under room temperature, 0.5-2h, obtains the compound of general formula 7;
5) in dichloromethane solvent, under room temperature, by the compound of general formula 7 and 30% hydrogen peroxide, stirring reaction 1-14h, obtains the compound of general formula 8;
6) at 80 DEG C-100 DEG C, the compound of general formula 5, the compound of general formula 8, salt of wormwood, potassiumiodide, DMF, stirring reaction 0.5-8h, obtains the compound of formula I;
9. a liquid-crystal composition, comprises one or more of compound as described in any one in claim 1 to 7.
10. one kind comprises the liquid crystal cell of liquid-crystal composition as claimed in claim 9.
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| CN103087724B (en) * | 2013-01-08 | 2015-02-04 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device comprising same |
| CN103361074B (en) * | 2013-07-01 | 2015-08-26 | 江苏和成新材料有限公司 | Comprise polyfluoro for the liquid crystalline cpd of unsaturated indenes ring and composition thereof and application |
| CN105331370B (en) * | 2014-07-22 | 2017-10-24 | 江苏和成显示科技股份有限公司 | Negative liquid crystal composition and its application |
| CN105331371B (en) * | 2014-07-22 | 2017-10-24 | 江苏和成显示科技股份有限公司 | Negative liquid crystal composition and its application |
| CN106675575B (en) * | 2015-11-06 | 2018-12-18 | 江苏和成显示科技有限公司 | A kind of dielectric negative liquid crystal compound and the preparation method and application thereof |
| CN105647542A (en) * | 2016-02-01 | 2016-06-08 | 北京华科嘉泰科技有限公司 | Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof |
| CN107267153B (en) * | 2016-04-08 | 2021-04-09 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound, composition and application thereof |
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