CN104099105A - Liquid crystal chemical compound containing dioxane ring and application thereof - Google Patents
Liquid crystal chemical compound containing dioxane ring and application thereof Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 78
- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 125000000532 dioxanyl group Chemical group 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 5
- -1 difluoro methoxyl Chemical group 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
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- 239000010409 thin film Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ALIOEWSAEJJWBA-UHFFFAOYSA-N 2-(3-fluoropropyl)propane-1,3-diol Chemical compound OCC(CO)CCCF ALIOEWSAEJJWBA-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- 239000005148 Cholesterol Benzoate Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VSTNCNVEYGFOEM-UHFFFAOYSA-N [4-[difluoro-(3,4,5-trifluorophenoxy)methyl]-3,5-difluorophenyl]boronic acid Chemical compound FC1=CC(B(O)O)=CC(F)=C1C(F)(F)OC1=CC(F)=C(F)C(F)=C1 VSTNCNVEYGFOEM-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- UVZUFUGNHDDLRQ-LLHZKFLPSA-N cholesteryl benzoate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)C1=CC=CC=C1 UVZUFUGNHDDLRQ-LLHZKFLPSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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Landscapes
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a liquid crystal chemical compound containing a dioxane ring and a difluoro methoxyl bridged bond. The liquid crystal chemical compound has a structure shown as the formula I in the Specification, and has the characteristics of large dielectric anisotropy, large optical anisotropy and high clearing point. After applied to a liquid crystal composition, the liquid crystal chemical compound, provided by the invention, can further ameliorate the dielectric anisotropy, the optical anisotropy and the clearing point of the existing idiomatic liquid crystal composition, and has the technical effects on lowering drive voltage and expanding temperature use range.
Description
Technical Field
The invention relates to the field of liquid crystal display materials, in particular to a liquid crystal compound containing dioxane ring and application thereof.
Background
Liquid crystals are now widely used in the field of information display, and have been used in optical communications (s.t.wu, d.k.yang.reflective liquid displays. wiley, 2001). In recent years, the application fields of liquid crystal compounds have been remarkably widened to various display devices, electro-optical devices, electronic components, sensors, and the like. For this reason, many different structures have been proposed, particularly in the field of nematic liquid crystals, which have hitherto been most widely used in flat panel displays. Particularly in systems with TFT active matrices.
Liquid crystal display has experienced a long development route along with the discovery of liquid crystals. In 1888, the first liquid crystal material, cholesterol benzoate, was discovered by the austria phytologist Friedrich reintzer. In 1917, Manguin invented rubbing alignment method to make single domain liquid crystal and study optical anisotropy. The theory of scraping (Swarm) was established by e.bose in 1909 and supported by l.s.ormstein and f.zernike et al (1918), which were later discussed as statistical fluctuations by De Gennes. Oseen and h.zocher created continuum theory in 1933 and was perfected by f.c. frank (1958). M.born (1916) and k.lichtennecker (1926) discovered and studied the dielectric anisotropy of liquid crystals. In 1932, w.kast accordingly classified the nematic phase into two main classes, positive and negative. In 1927, v.freedericksz and v.zolonao found that nematic liquid crystals deformed under the action of an electric (or magnetic) field and had a voltage threshold (Freederichsz transition). This finding provides the basis for the fabrication of liquid crystal displays.
In 1968, R.Williams, RCA corporation in America, discovered that nematic liquid crystals form fringe domains under the action of an electric field and have a light scattering phenomenon. The g.h.heilmeir was subsequently developed into a dynamic scattering display mode and made the first Liquid Crystal Display (LCD) in the world. In the early seventies, Helfrich and Schadt invented the TN principle, and people made them into display devices (TN-LCD) by using the combination of TN photoelectric effect and integrated circuit, thus developing a broad prospect for the application of liquid crystal. Since the seventies, the application of liquid crystal in display has been developed in a breakthrough due to the development of large-scale integrated circuits and liquid crystal materials, and the Super Twisted Nematic (STN) mode proposed by t.scheffer et al in 1983-1985 and the Active Matrix (AM) mode proposed by p.brody in 1972 were adopted again. Conventional TN-LCD technology has been developed into STN-LCD and TFT-LCD technology, and although STN has scan lines up to 768 or more, problems of response speed, viewing angle and gray scale still exist when temperature rises, thus large area, high information content, high data rate, and the like,
The color display is mostly an active matrix display system. TFT-LCD has been widely used in direct view televisions, large screen projection televisions, computer terminal displays and some military instrument displays, and TFT-LCD technology is believed to have wider application prospects.
Where "active matrix" includes two types: 1. OMS (metal oxide semiconductor) or other diodes on a silicon wafer as a substrate. 2. A Thin Film Transistor (TFT) on a glass plate as a substrate.
The use of single crystal silicon as a substrate material limits the display size because of the many problems that arise with the assembly of parts of the display device and even the modules at their junctions. Thus, the second type of thin film transistor is a promising type of active matrix, and the photoelectric effect utilized is typically the TN effect. TFTs include compound semiconductors, such as CdSe, or TFTs based on polycrystalline or amorphous silicon.
At present, the technology of TFT-LCD products is mature, the technical problems of visual angle, resolution, color saturation, brightness and the like are successfully solved, and the display performance of the TFT-LCD products is close to or exceeds that of a CRT display. Large-sized and medium-sized TFT-LCD displays have gradually occupied the mainstream position of flat panel displays in their respective fields. However, the TFT-LCD still has many defects, such as not fast response, not low voltage, not high charge retention rate, etc., due to the limitation of the liquid crystal material itself. Therefore, it is important to find a single crystal compound having a low viscosity and a high dielectric anisotropy.
The German Merck company, as early as 1990, has disclosed a combination of F (CH2)nThe synthesis of monomeric liquid crystals of dioxane and dioxane is illustrated, and the corresponding compounds obtained are not ideal for use in liquid crystal compositions.
The synthesis method of the monomer liquid crystal is also described in patent WO9820006 of Japanese Chilean company in 1996, and the obtained corresponding compound has not ideal comprehensive performance.
Disclosure of Invention
Against the above background, an object of the present invention is to provide a novel liquid crystal compound having characteristics of large dielectric anisotropy, large optical anisotropy and high clearing point.
The invention provides a liquid crystal compound with a dioxane ring, which simultaneously contains the dioxane ring and a difluoromethoxy bridge bond and has a structure shown in a formula I:
wherein,
A1and A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms;
x is selected from F, OCF3、OCHF2、CF3、CF2H、Cl、OCH＝CF2Or OCF2CF＝CF2；
Y1And Y2Each independently represents H or F;
n is 2 to 10.
Preferably, in the liquid crystal compound,
A1and A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms;
x is selected from F, OCF3、OCHF2Or CF3；
Y1And Y2Each independently represents H or F, and is not simultaneously H;
n is 2, 3 or 4.
Further preferably, in the liquid crystal compound,
A1and A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms;
x is selected from F or OCF3；
Y1And Y2Each independently represents H or F, and is not simultaneously H;
n is 2, 3 or 4.
More preferably, the liquid crystal compound is selected from compounds of the following general structure:
wherein X is selected from F or OCF3(ii) a n is 2, 3 or 4.
In a preferred embodiment of the present invention, the liquid crystal compound has a structure of:
the liquid crystal compound has the remarkable characteristics of large dielectric anisotropy, large optical anisotropy and high clearing point. After the compound is applied to the composition, the composition has the characteristics of low driving voltage and wide temperature use range.
The second purpose of the invention is to provide a preparation method of a liquid crystal compound containing a dioxane ring, and the synthesis route of the preparation method is as follows:
the method comprises the following steps:
1) starting raw material compounds II and III, taking methylbenzene as a solvent and p-toluenesulfonic acid as a dehydration catalyst, and heating, refluxing and dehydrating for 3-9 hours to obtain a compound IV;
2) and carrying out reflux reaction on the compound IV and the compound V for 4-12 hours by using tetratriphenylphosphine palladium as a catalyst to obtain a target compound I.
Wherein,
A1、A2、X、Y1、Y2and n is as above;
the reflux time in step 2) is preferably 6 hours.
By adopting the preparation method, the liquid crystal compound containing the dioxane ring can be stably obtained in batches, and the compound has the advantages of large dielectric anisotropy, large optical anisotropy and high clearing point.
The third purpose of the invention is to protect the application of the liquid crystal compound containing the dioxane ring in the field of liquid crystal display.
The invention claims liquid crystal compositions containing liquid crystal compounds with dioxane ring. In the composition, a liquid crystal compound containing a dioxane ring is added in a reasonable mode, and the liquid crystal compound accounts for 1-80% by mass of the liquid crystal composition, preferably 3-50% by mass of the liquid crystal composition. It is expected that the dielectric anisotropy, optical anisotropy and clearing point of the existing conventional liquid crystal composition can be further improved based on the addition of the above liquid crystal compound, and the technical effects of reducing the driving voltage and widening the temperature use range can be achieved.
The present invention further claims the use of the above liquid crystal composition in liquid crystal display devices including, but not limited to, TN, ADS, FFS, IPS, VA or PSVA liquid crystal displays. After the liquid crystal composition is applied to a liquid crystal display device, the liquid crystal display device has the advantages of low driving voltage and wide temperature use range.
The abbreviations of the performance test parameters in the invention are as follows:
Δ ε represents the dielectric anisotropy at 25 ℃ and 1 kHz;
Δ n represents optical anisotropy;
γ 1 represents the rotational viscosity (mPas) at 25 ℃;
no represents refractive index (589nm,25 ℃);
c.p represents the clearing point (. degree. C.) of the liquid crystal composition;
VHR represents charge retention (%); the measuring method comprises the following steps: injecting the mixed liquid crystal into a liquid crystal box, putting the liquid crystal into a thermostat, entering a test program after the temperature is stable, and manually taking points to obtain a charge retention rate value; the measurement voltage was 5V, the power-up time was 5ms, and the hold time was 500 ms.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
2- {4' - [1- (3,4, 5-Trifluorophenoxy) difluoromethyl]-3',5' -difluorobiphenyl } -5- (3-fluoropropyl) - [1,3]]Synthesis of dioxane (Compound 5)
1) Synthesis of 2- (4-bromophenyl) -5- (3-fluoropropyl) - [1,3] dioxane (Compound 3):
to a 500mL three-necked flask were added 0.3L of toluene, 31.5g of p-bromobenzaldehyde (Compound 2), 23.1g of 2- (3-fluoropropyl) -1, 3-propanediol (Compound 1), and 1.2g of p-toluenesulfonic acid. Stirring and heating are started, and the reflux reaction is carried out for 3 hours. After the post-treatment, washing with 0.2L multiplied by 2 water, combining organic phases, adding 20g of anhydrous sodium sulfate, drying for 0.5h, spin-drying the solvent, adding 150mL of toluene and 150mL of petroleum ether, passing through 30g of silica gel column, and passing through 3 times column high-washing column. The solvent was spin-dried to 67g, 2 times ethanol and 0.5 time toluene were added, and the mixture was frozen in a refrigerator (-30 ℃ C.) and suction-filtered overnight. The product was a white solid with a gas phase purity (GC) of 99.0%, a theoretical yield of 51.3g, an actual yield of 27.1g, a yield of 53%.
2) Synthesis of 2- {4' - [1- (3,4, 5-trifluorophenoxy) difluoromethyl ] -3',5' -difluorobiphenyl } -5- (3-fluoropropyl) - [1,3] dioxane (compound 5):
a200 mL three-necked flask was charged with 26mL of anhydrous ethanol, 50mL of toluene, and 50mL of water, with stirring, and charged with 19.5g of 4- [1- (3,4, 5-trifluorophenoxy) difluoromethyl ] -3, 5-difluorophenylboronic acid (Compound 4), 15.2g of 2- (4-bromophenyl) -5- (3-fluoropropyl) - [1,3] dioxane (Compound 3), and 11.7g of anhydrous sodium carbonate. The nitrogen was replaced with air three times and 0.25g of tetrakis (triphenylphosphine) palladium was added. Heating to liquid phase 60 deg.C, heating slowly to reflux, and reflux reacting for 6 hr. After completion of the reflux, 40mL of water was added to the reaction vessel, and the mixture was stirred for 10 minutes, allowed to stand for liquid separation, and the organic phase was washed twice with 40mL of 2 water. Adding 3 times of petroleum ether, heating for dissolving, and performing column chromatography. And (4) freezing and recrystallizing the spin-dried solvent for three times by using 4 times of ethanol, and filtering and airing to obtain a white solid.
The obtained product is:
the theoretical yield is 26.6g, the actual yield is 21.5g, and the yield is 80.8%;
gas phase purity (GC) 99.9%;
melting point: 80.0 ℃;
clearing the bright spots: 109.1 ℃;
Δn：0.144；
Δε：33.46；
γ1：125mPa·s；
mass spectrometry fragmentation: 239. 267, 385, 532 (molecular ion peaks);
H-NMR Nuclear magnetic Spectroscopy (CDCl,300 MHz): δ H: 0.90-2.60(m,5H),3.50-5.90(m,7H),6.20-7.50(m, 8H).
According to the technical scheme of example 1, the following compounds can be synthesized by substituting raw materials containing corresponding groups:
example 2
The liquid crystal monomers used in the following compositions are all available from the company of the Beijing eight billion space-time liquid Crystal technology, Inc. Except for special indication, the contents of each component in the examples all represent weight percent.
The following liquid crystal compounds are taken and prepared into liquid crystal compositions in parts by weight, and the specific mixture ratio and the performance parameters of the obtained liquid crystal compositions are shown in tables 1 and 2.
Table 1: the liquid crystal composition containing the compound of the invention comprises various components and performance parameters
Table 2: liquid crystal composition containing no compound and its components and performance parameters
Comparing table 1 and table 2, it can be seen that: the liquid crystal composition added with the compound provided by the invention has the advantages that the dielectric anisotropy is remarkably increased from 4.86 to 7.72, the optical anisotropy and clearing point are slightly increased, and the rotational viscosity and the charge retention rate are basically kept unchanged.
In addition to the compositions exemplified in the experimental examples, other liquid crystal compositions to which other liquid crystal compounds having a dioxane ring and difluoromethoxy bridge structure provided by the present invention were added were able to obtain the same excellent optical and electrical properties.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can 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 (10)
1. A liquid crystal compound containing a dioxane ring, wherein the liquid crystal compound has a structure represented by formula I:
wherein,
A1and A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms;
x is selected from F, OCF3、OCHF2、CF3、CF2H、Cl、OCH＝CF2Or OCF2CF＝CF2；
Y1And Y2Each independently represents H or F;
n is 2 to 10.
2. The compound of claim 1, wherein a is1And A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms; x is selected from F, OCF3、OCHF2Or CF3；Y1And Y2Each independently represents H or F, and is not simultaneously H; n is 2, 3 or 4.
3. The compound of claim 2, wherein a is1And A2Each independently represents 1, 4-phenyl, in which one or more H atoms may be substituted by F atoms; x is selected from F or OCF3；Y1And Y2Each independently represents H or F, and is not simultaneously H; n is 2, 3 or 4.
4. The compound of claim 3, wherein the liquid crystal compound is selected from compounds of the following general structures:
wherein X is selected from F or OCF3(ii) a n is 2, 3 or 4.
5. The compound of claim 4, wherein the compound has the structure:
6. a method for producing the liquid crystal compound according to any one of claims 1 to 5, characterized by comprising the steps of:
1) starting raw material compounds II and III, taking methylbenzene as a solvent and p-toluenesulfonic acid as a dehydration catalyst, and heating, refluxing and dehydrating for 3-9 hours to obtain a compound IV;
2) carrying out reflux reaction on the compound IV and the compound V for 4-12 hours by using palladium tetratriphenylphosphine as a catalyst to obtain a target compound I;
wherein A is1、A2、X、Y1、Y2And n is as defined in any one of claims 1 to 5.
7. Use of the liquid crystal compound according to any one of claims 1 to 5 in the field of liquid crystal displays.
8. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 5, wherein the liquid crystal compound is contained in the liquid crystal composition in an amount of 1 to 80% by mass.
9. The composition according to claim 8, wherein the liquid crystal compound is 3 to 50% by mass of the liquid crystal composition.
10. Use of the composition of claim 8 or 9 for the manufacture of a liquid crystal display device comprising a TN, ADS, FFS, IPS, VA or PSVA liquid crystal display.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104130781A (en) * | 2014-07-03 | 2014-11-05 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| CN104263382A (en) * | 2014-09-11 | 2015-01-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composite containing 1,3-dioxane and difluoromethoxy bridge-bond compound and application of liquid crystal composite |
| CN105018108A (en) * | 2015-06-10 | 2015-11-04 | 北京华科嘉泰科技有限公司 | Liquid crystal composition containing 1,3-dioxane compound and application thereof |
| WO2016082511A1 (en) * | 2014-11-27 | 2016-06-02 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| WO2016082510A1 (en) * | 2014-11-27 | 2016-06-02 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| US10584086B2 (en) | 2014-11-20 | 2020-03-10 | Beijing Bayi Space Lcd Technology Co., Ltd | Liquid crystal compound containing a difluormethoxy bridge and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998020006A1 (en) * | 1996-11-07 | 1998-05-14 | Chisso Corporation | Fluoroalkylated dioxane derivatives, liquid crystal compositions, and liquid-crystal display elements |
| CN1182085A (en) * | 1996-07-15 | 1998-05-20 | 智索公司 | Phenyldioxane derivatives, liquid crystal compositions, and liquid crystal display elements |
| CN101143808A (en) * | 2006-09-13 | 2008-03-19 | 默克专利股份有限公司 | Fluorine phenyl compounds for liquid crystalline mixtures |
| CN103724168A (en) * | 2014-01-17 | 2014-04-16 | 石家庄诚志永华显示材料有限公司 | Difluoro methoxy bond derivative containing deuterium as well as preparation method and application of derivative |
| WO2014065293A1 (en) * | 2012-10-23 | 2014-05-01 | Jnc株式会社 | Liquid-crystal compound, liquid-crystalline medium and optical element |
| CN103773386A (en) * | 2014-01-27 | 2014-05-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing 1,4-dioxane and pentafluoro-allyloxy structure and liquid crystal composition thereof |
-
2014
- 2014-06-30 CN CN201410306790.6A patent/CN104099105A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1182085A (en) * | 1996-07-15 | 1998-05-20 | 智索公司 | Phenyldioxane derivatives, liquid crystal compositions, and liquid crystal display elements |
| WO1998020006A1 (en) * | 1996-11-07 | 1998-05-14 | Chisso Corporation | Fluoroalkylated dioxane derivatives, liquid crystal compositions, and liquid-crystal display elements |
| CN101143808A (en) * | 2006-09-13 | 2008-03-19 | 默克专利股份有限公司 | Fluorine phenyl compounds for liquid crystalline mixtures |
| WO2014065293A1 (en) * | 2012-10-23 | 2014-05-01 | Jnc株式会社 | Liquid-crystal compound, liquid-crystalline medium and optical element |
| CN103724168A (en) * | 2014-01-17 | 2014-04-16 | 石家庄诚志永华显示材料有限公司 | Difluoro methoxy bond derivative containing deuterium as well as preparation method and application of derivative |
| CN103773386A (en) * | 2014-01-27 | 2014-05-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing 1,4-dioxane and pentafluoro-allyloxy structure and liquid crystal composition thereof |
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| CN104130781A (en) * | 2014-07-03 | 2014-11-05 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| CN104130781B (en) * | 2014-07-03 | 2016-05-11 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal composition and application thereof |
| CN104263382A (en) * | 2014-09-11 | 2015-01-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composite containing 1,3-dioxane and difluoromethoxy bridge-bond compound and application of liquid crystal composite |
| CN104263382B (en) * | 2014-09-11 | 2016-04-06 | 北京八亿时空液晶科技股份有限公司 | Containing liquid-crystal composition and the application thereof of 1,3-diox and difluoro-methoxy bridged bond compound |
| US10584086B2 (en) | 2014-11-20 | 2020-03-10 | Beijing Bayi Space Lcd Technology Co., Ltd | Liquid crystal compound containing a difluormethoxy bridge and application thereof |
| WO2016082510A1 (en) * | 2014-11-27 | 2016-06-02 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| WO2016082511A1 (en) * | 2014-11-27 | 2016-06-02 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| JP2017529449A (en) * | 2014-11-27 | 2017-10-05 | 北京八億時空液晶科技股▲ふん▼有限公司Ｂｅｉｊｉｎｇ Ｂａｙｉ Ｓｐａｃｅ Ｌｃｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．，Ｌｔｄ | Liquid crystal compound having difluoromethoxy crosslink, composition and application thereof |
| JP2017529450A (en) * | 2014-11-27 | 2017-10-05 | 北京八億時空液晶科技股▲ふん▼有限公司Ｂｅｉｊｉｎｇ Ｂａｙｉ Ｓｐａｃｅ Ｌｃｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．，Ｌｔｄ | Liquid crystal compound having difluoromethoxy crosslink, composition and application thereof |
| KR20170121151A (en) * | 2014-11-27 | 2017-11-01 | 베이징 바이 스페이스 엘시디 테크놀로지 컴퍼니 리미티드 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| US10494569B2 (en) | 2014-11-27 | 2019-12-03 | Beijing Bayi Space Lcd Technology Co., Ltd | Liquid crystal compound containing difluoromethoxy bridge, composition and application thereof |
| US10494570B2 (en) | 2014-11-27 | 2019-12-03 | Beijing Bayi Space Lcd Technology Co., Ltd | Liquid crystal compound containing difluormethoxy bridge, composition and application thereof |
| KR102347008B1 (en) | 2014-11-27 | 2022-01-03 | 베이징 바이 스페이스 엘시디 테크놀로지 컴퍼니 리미티드 | Liquid crystal compound containing difluoromethoxy bridging, composite, and applications thereof |
| CN105018108B (en) * | 2015-06-10 | 2017-03-29 | 北京华科嘉泰科技有限公司 | A kind of liquid-crystal composition for containing 1,3 diox compounds and its application |
| CN105018108A (en) * | 2015-06-10 | 2015-11-04 | 北京华科嘉泰科技有限公司 | Liquid crystal composition containing 1,3-dioxane compound and application thereof |
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