CN108659851A - A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond - Google Patents
A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
Abstract
The present invention relates to a kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond.The liquid-crystal compounds has the structure such as general formula I.Advantageous effect：The present invention introduces negativity polar group in positive liquid crystal molecules structure, both improves penetrance, is provided simultaneously with the fast response time, and ultraviolet stability is good, to improve the contrast of liquid crystal display.
Description
Technical field
The present invention relates to a kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond, belongs to liquid
Brilliant display material field.
Background technology
Liquid crystal has been widely applied to computer, the display screen of laptop, LCD TV etc. now.Use liquid crystal
Doing the basic principle of display material is：As the variation liquid crystal molecule of electric field strength can do regular 90 degree of rotations, to change
Become light transmittance, liquid crystal can from it is unordered it is transparent become orderly nontransparent, will produce the variation of light and shade, can be controlled according to this principle
The light and shade of each pixel on image, to constitute required image.
The display mode of liquid crystal simultaneously differs, and can probably be divided into thin film transistor liquid crystal display (TFT-LCD), cholesteric nematic
Phase transformation liquid crystal display (CH-N), Supertwist Nematic Liquid Crystal Display (STN-LCD), guest-host type liquid crystal display (GH-LCD), distort to
Row liquid crystal display (TN-LCD), polymer scattering type liquid crystal show that (PDLC), ferroelectric liquid crystals are shown (FLCD).If only using TN
Type liquid crystal, then it is mainly to be needed thus based on crocus and light green that display, which only has two kinds of colors of black and white, STN displays,
To it plus one layer of optical filter with chromatic colour, it can show that three primary colors, three primary colors pass through certain ratio when passing through optical filter
Display can show coloured image.TFT is then provided with thin film transistor (TFT) at its back, its effect is each on control screen
Independent pixel, this control can significantly improve the fluency that image is shown, contrast also can it is more apparent simultaneously as it
Have the features such as higher voltage retention, low-refraction, low-viscosity, even if still display is clear under the conditions of light is stronger
It is clear, commonly referred to as true color, so TFT-LCD is display common in the market.
There are a variety of different display patterns, more competitive display pattern mainly to have currently on the market, face inscribe
Change (in-plane switching, IPS) fringing field switching (fringe-field switching, FFS), and vertical arrangement
Display patterns such as (vertical alignment, VA).In these display patterns, in-plane switching (IPS) and fringing field switching
(FFS) all has the characteristics that wide viewing angle.Quick response can be obtained when positivity liquid crystal is used for IPS/FFS display patterns, and
There is good reliability；And negative liquid crystal is used to obtain higher transmitance when IPS/FFS display patterns, but due to negative
Property liquid crystal viscosity is bigger, so response speed is slower.
For current wide viewing angle display pattern IPS in-plane switchings (in-pline switching, IPS), fringing field is cut
It changes (fringe-field switching, FFS), in both patterns, positivity liquid crystal and negative liquid crystal are on light transmission rate
Difference is mainly reflected in the transmitance efficiency of the liquid crystal at pixel electrode interval center.Because at pixel electrode interval center,
The elastic strength of positive liquid crystal molecules rotation is weaker than negative liquid crystal.If positivity liquid crystal will obtain identical light using effect
Rate, △ nd values are bigger than negative liquid crystal.So being directed to both the above pattern, solution before is improved from liquid crystal angle
Penetrance can add negativity component in positivity liquid crystal.
And negative liquid crystal compound due in synthetic method and treatment process in the difference of positivity liquid crystal, usual negativity liquid
Brilliant molecule by UV after irradiating, and voltage retention and resistivity can reduce significantly, i.e. negative liquid crystal molecule phase
Compared with for positive liquid crystal molecules have poor ultraviolet stability.In addition to this, negative liquid crystal molecule is usually compared with positivity molecule
With larger viscosity, it is unfavorable for the raising of response time.
Invention content
The present invention in view of the above shortcomings of the prior art, provides a kind of liquid-crystal compounds containing difluoro-methoxy bridged bond.
The liquid-crystal compounds both improves penetrance, is provided simultaneously with the fast response time, and ultraviolet stability is good, to improve liquid crystal
Show the contrast of device.
The technical solution that the present invention solves above-mentioned technical problem is as follows：
A kind of liquid-crystal compounds containing difluoro-methoxy bridged bond, the compound have logical structure shown in formula I：
Wherein, R1It is independent to indicate that H atom, containing 1~7 carbon atom or arbitrary H atom are contained by what F atom replaced
The alkyl of 1~7 carbon atom, the alkoxy containing 1~6 carbon atom or arbitrary H atom contain 1~6 by what F atom replaced
The alkoxy of carbon atom, the alkenyl containing 2~6 carbon atoms or arbitrary H atom contain 2~6 carbon originals by what F atom replaced
The alkenyl of son and alkenyloxy containing 3~5 carbon atoms or arbitrary H atom contain 3~5 carbon originals by what F atom replace
One kind in the alkenyloxy of son；
Independent expression
Indicate one or more in following groups:
L1、L2It is separate to indicate H or F atom respectively；
X1Halogenated alkyl that the independent alkyl, carbon atom number for indicating that F, Cl, carbon atom number are 1-6 is 1-6, carbon atom number
For the alkylene of 2-6, carbon atom number be 2-6 haloalkene alkyl, carbon atom number be 1-6 halogenated alkoxy or carbon atom number be
Any one in the haloalkenyloxy of 2-6；
M indicates 0 or 1.
Further, the R1Indicate the alkyl containing 1~6 carbon atom or the alkoxy containing 1~5 carbon atom；
X1The halogenated alkoxy or carbon that the independent halogenated alkyl, carbon atom number for indicating that F, carbon atom number are 1-6 is 2-5 are former
Subnumber is any one of the haloalkenyloxy of 2-5.
Further, the one kind of the compound of the general formula I in following general formula I -1 to I -12：
R1Indicate the alkyl containing 1~5 carbon atom.
Advantageous effect：The present invention introduces negativity polar group in positive liquid crystal molecules structure, both improves penetrance, together
When have the fast response time, ultraviolet stability is good, to improve the contrast of liquid crystal display.
The method such as the above-mentioned liquid-crystal compounds with logical structure shown in formula I is prepared the present invention also provides a kind of, including as follows
Step：
(1) compound a passes through grignard, suzuki coupling synthesis compounds b；
(2) after the compound b takes hydrogen by force by highly basic, with after two bromine reaction of difluoro compound c；
(3) the compound c obtains final compound under alkaline condition with phenol.
Further, the highly basic is butyl lithium, LDA, potassium tert-butoxide, HMDSLi or sodium hydrogen.
The present invention also provides a kind of liquid-crystal compositions, including the liquid described in any one of the above embodiments containing difluoro-methoxy bridged bond
Brilliant compound.
Further, the quality of the liquid-crystal compounds accounts for the 1-70% of the liquid-crystal composition gross mass.
Further, the quality of the liquid-crystal compounds accounts for the 3-50% of the liquid-crystal composition gross mass.
The present invention also provides a kind of such as application of the above-mentioned liquid-crystal composition in field of liquid crystal.
Specific implementation mode
Illustrate the present invention below with reference to specific embodiment.It should be noted that the following examples are the present invention
Example, be only used for illustrating the present invention, and be not limited to the present invention.Without departing from present subject matter or range,
It can carry out other combinations and the various improvement in present inventive concept.
Embodiment 1
Scheme:
1 40g is to propyl bromobenzene, 54g butyl borates, 200ml THF mixing；20ml mixed liquors are instilled at 60 DEG C
Into the three-necked flask containing 5.7g magnesium chips nitrogen protections, 4 drop bromoethanes cause；After reaction causes, residual mixed liquor is instilled,
Temperature is at 65 DEG C in control, after dripping, 68 DEG C of heat preservation 4h.It is cooling, 20ml concentrated hydrochloric acids are added and 200ml water stirs 0.5h, are added
200mlEA, layering；Organic phase saturated common salt water washing 3 times, it is dry, it is spin-dried for, is recrystallized at -10 DEG C with 100ml petroleum ethers,
Obtain 29.5g compounds 1.
2 29.5g compounds, 1,38.2g2,3,5- trifluorobromobenzene, 60g potassium phosphates, tetra- triphenyl phosphorus palladiums of 0.5g, 300ml first
Benzene stirs 8h for 90 DEG C under nitrogen protection.It is cooling, with saturated common salt water washing organic phase 3 times, anhydrous sodium sulfate drying, filtering,
It is spin-dried for, distills to obtain 40g compounds 2.
3 40g compounds 2 are dissolved in 200mlTHF, are cooled to -78 DEG C, and 84ml butyl lithiums are instilled at -78 DEG C, stirring
1h.At -78 DEG C, 35g difluorodibromomethanes are instilled, are warmed to room temperature naturally, stirs 6h.300ml toluene is added and 300ml contains
There is the water of 15ml concentrated hydrochloric acids, stir 0.5h, layering obtains organic layer.Organic phase is spin-dried for, and obtains 60g compounds 3.
4 60g compounds 3,24g 3,4,5- trifluoromethyl phenols, 17g potassium carbonate 50 DEG C of stirring 8h in 200mlTHF.It is spin-dried for,
200ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, recrystallizes 2 times to obtain 30g I -1 at 0 DEG C with ethyl alcohol.
Purity:99.9%.
Embodiment 2
Scheme:
Bis- fluoro- 4- bromophenols of 1 20.9g 2,6-, 21g perfluoro 3- bromopropenes, 13g potassium carbonate is 50 in 150ml THF
DEG C stirring 8h.It is spin-dried for, 200ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, distills to obtain 30g compounds 4.
2 30g compounds 4 are dissolved in 200mlTHF, are cooled to -78 DEG C, and 40ml butyl lithiums are instilled at -78 DEG C, stirring
1h.At -78 DEG C, 23g butyl borates are instilled, are warmed to room temperature naturally, stirs 6h.200ml toluene is added and 100ml contains
The water of 20ml concentrated hydrochloric acids, stirs 0.5h, and layering obtains organic layer.Organic phase is spin-dried for, addition 100mlTHF, 120g hydrogen peroxide, 25 DEG C
Lower stirring 12h.It is spin-dried for, with 30g 1：1=ethyl alcohol：Water mixed liquid recrystallizes, and obtains 19.3g compounds 5.
3 19.3g compounds 5,10.3g 3,4,5- trifluoromethyl phenols, 8.2g potassium carbonate 50 DEG C of stirring 8h in 200mlTHF.
It is spin-dried for, 200ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, recrystallizes 2 times to obtain 20g at 10 DEG C with ethyl alcohol
Ⅰ-2.Purity:99.9%.
Embodiment 3
Scheme:
1 20.9g, 2,3,5- trifluorobromobenzenes are dissolved in 150mlTHF, -78 DEG C are cooled to, by 44ml butyl lithiums at -78 DEG C
1h is stirred in lower instillation.At -78 DEG C, 7.3g DMF are instilled, are warmed to room temperature naturally, stirs 6h.Be added 200ml toluene and
100ml contains the water of 12ml concentrated hydrochloric acids, stirs 0.5h, layering；Organic phase is dried, and 14.4 compounds 6 are spin-dried for obtaining.
2 14.4g compounds 6,11.8g 2- n-propyl propane -1,3- glycol, 0.02g p-methyl benzenesulfonic acids, 100ml first
Benzene reflux water removal 8h.
Reaction solution is cooled to -78 DEG C in 3 steps 2, and 40ml butyl lithiums are instilled at -78 DEG C, stirs 1h.At -78 DEG C,
20g difluorodibromomethanes are instilled, are warmed to room temperature naturally, 6h is stirred.150ml toluene is added and 150ml contains 7.5ml concentrated hydrochloric acids
Water, stir 0.5h, layering, obtain organic layer.Organic phase is spin-dried for, and obtains 31g compounds 8.
4 31g compounds, 8,11.8g3,4,5- trifluoromethyl phenol, 9.5g potassium carbonate 50 DEG C of stirring 8h in 200mlTHF.Rotation
It is dry, 200ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, recrystallizes 2 times to obtain 15g I-at 10 DEG C with ethyl alcohol
5.Purity:99.9%.
Embodiment 4
Scheme:
Compound 8 prepared by 1 31g embodiments 3, the compound 5 prepared by 22g embodiments 2,9.5g potassium carbonate exist
50 DEG C of stirring 8h in 200mlTHF.Be spin-dried for, 200ml toluene be added, is washed with deionized 4 times, it is dry, be spin-dried for, with ethyl alcohol-
18g I -6 is recrystallized 2 times to obtain at 10 DEG C.Purity:99.9%.
Embodiment 5
Scheme:
1 27.5g is to bromopropyl biphenyl, 25g butyl borates, 200ml THF mixing；The 20ml mixing drop at 60 DEG C
Enter into the three-necked flask containing 2.5g magnesium chips nitrogen protections, 4 drop bromoethanes cause；After reaction causes, residual mixed liquor is dripped
Enter, controls interior temperature at 65 DEG C, after dripping, 68 DEG C keep the temperature 4h.It is cooling, 10ml concentrated hydrochloric acids are added and 200ml water stirs 0.5h, add
Enter 200mlEA, is layered；Organic phase saturated common salt water washing 3 times, it is dry, it is spin-dried for, is recrystallized at -10 DEG C with 50ml petroleum ethers,
Obtain 21.6g compounds 9.
2 21.6g compounds, 9,19.1g2,3,5- trifluorobromobenzene, 30g potassium phosphates, tetra- triphenyl phosphorus palladiums of 0.3g, 200ml first
Benzene stirs 8h for 90 DEG C under nitrogen protection.It is cooling, with saturated common salt water washing organic phase 3 times, anhydrous sodium sulfate drying, filtering,
It is spin-dried for, ethyl alcohol recrystallization obtains 22.8g compounds 10.
3 22.8g compounds 10 are dissolved in 200mlTHF, are cooled to -78 DEG C, and 30ml butyl lithiums are instilled at -78 DEG C,
Stir 1h.At -78 DEG C, 17g difluorodibromomethanes are instilled, are warmed to room temperature naturally, stirs 6h.Be added 150ml toluene and
150ml contains the water of 7.5ml concentrated hydrochloric acids, stirs 0.5h, and layering obtains organic layer.Organic phase is spin-dried for, and obtains 31.7g compounds 11.
4 31.7g compounds 11,11g 3,4,5- trifluoromethyl phenols, 7.5g potassium carbonate 50 DEG C of stirring 8h in 100mlTHF.
It is spin-dried for, 100ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, is recrystallized 2 times under 0 degree Celsius with ethyl alcohol
15g Ⅰ-7.Purity:99.9%.
Embodiment 6
Scheme:
1 21.1g, 2,3,5- trifluorobromobenzenes, 25g butyl borates, 200ml THF mixing；The 20ml mixed liquors at 60 DEG C
It is added dropwise in the three-necked flask containing 2.5g magnesium chips nitrogen protections, 4 drop bromoethanes cause；After reaction causes, by residual mixed liquor
It instills, controls interior temperature at 65 DEG C, after dripping, 68 DEG C keep the temperature 4h.It is cooling, 10ml concentrated hydrochloric acids are added and 200ml water stirs 0.5h,
200mlEA, layering is added；Organic phase saturated common salt water washing 3 times, it is dry, it is spin-dried for, is tied again at -10 DEG C with 50ml petroleum ethers
Crystalline substance obtains 15.8g compounds 12.
2 15.8g compounds 12,16.6g p-bromobenzaldehydes, 30g potassium phosphates, tetra- triphenyl phosphorus palladiums of 0.3g, 200ml toluene,
90 DEG C of stirring 8h under nitrogen protection.Cooling, with saturated common salt water washing organic phase 3 times, anhydrous sodium sulfate drying is filtered, rotation
It is dry, distill to obtain 18.8g compounds 13.
3 18.8g compounds 13,9.4g 2- n-propyl propane -1,3- glycol, 0.02g p-methyl benzenesulfonic acids, 100ml first
Benzene reflux water removal 8h.
Reaction solution is cooled to -78 DEG C in 4 steps 2, and 36ml butyl lithiums are instilled at -78 DEG C, stirs 1h.At -78 DEG C,
19g difluorodibromomethanes are instilled, are warmed to room temperature naturally, 6h is stirred.150ml toluene and 150ml water is added, stirs 0.5h, point
Layer, obtains organic layer.Organic phase is spin-dried for, and obtains 37g compounds 15.
5 37g compounds 15,11.8g 3,4,5- trifluoromethyl phenols, 8.5g potassium carbonate 50 DEG C of stirring 8h in 100mlTHF.
It is spin-dried for, 100ml toluene is added, is washed with deionized 4 times, it is dry, it is spin-dried for, is recrystallized 2 times under 0 degree Celsius with ethyl alcohol
25gⅠ-11.Purity:99.9%.
Liquid-crystal compounds of the present invention has rotary viscosity low, and higher clearing point, stability and anti-UV abilities are good, mutually
The features such as dissolubility is good.It uses F atom instead of H atom since the phenyl ring 2 before difluoro-methoxy bridged bond is upper, increases vertical
In the dielectric of liquid crystal long axis direction, in IPS-TFT, FFS-TFT display patterns, transmitance is improved by a relatively large margin, and because
The monocrystalline of negative dielectric anisotropic need not specially be added in system, therefore stable system system and anti-UV abilities also have and greatly carry
It is high.
The present invention can be summarized with others without prejudice to the concrete form of the spirit or essential characteristics of the present invention.Therefore, nothing
By from the point of view of which point, the embodiment above of the invention can only all be considered the description of the invention and cannot limit this hair
Bright, claims indicate the scope of the present invention, and above-mentioned explanation does not point out the scope of the present invention, therefore, with this
Any change in the comparable meaning and scope of claims of invention is all considered as being included in the claim of the present invention
In the range of book.
Claims (9)
1. a kind of liquid-crystal compounds containing difluoro-methoxy bridged bond, which is characterized in that the compound has logical structure shown in formula I：
Wherein, R1It is independent to indicate that H atom, containing 1~7 carbon atom or arbitrary H atom contain 1~7 by what F atom replace
The alkyl of a carbon atom, the alkoxy containing 1~6 carbon atom or arbitrary H atom contain 1~6 carbon original by what F atom replaced
The alkoxy of son, the alkenyl containing 2~6 carbon atoms or arbitrary H atom by F atom replace containing 2~6 carbon atoms
Alkenyl and alkenyloxy containing 3~5 carbon atoms or arbitrary H atom by F atom replace containing 3~5 carbon atoms
One kind in alkenyloxy；
Independent expression
Indicate one or more in following groups:
L1、L2It is separate to indicate H or F atom respectively；
X1Halogenated alkyl that the independent alkyl, carbon atom number for indicating that F, Cl, carbon atom number are 1-6 is 1-6, carbon atom number 2-6
Alkylene, carbon atom number be 2-6 haloalkene alkyl, carbon atom number be 1-6 halogenated alkoxy or carbon atom number be 2-6's
Any one in haloalkenyloxy；
M indicates 0 or 1.
2. the liquid-crystal compounds according to claim 1 containing difluoro-methoxy bridged bond, which is characterized in that the R1It indicates
Alkyl containing 1~6 carbon atom or the alkoxy containing 1~5 carbon atom；
X1The halogenated alkoxy or carbon atom number that the independent halogenated alkyl, carbon atom number for indicating that F, carbon atom number are 1-6 is 2-5
For any one of the haloalkenyloxy of 2-5.
3. the liquid-crystal compounds according to claim 2 containing difluoro-methoxy bridged bond, which is characterized in that the general formula I
One kind in following general formula I -1 to I -12 of compound：
R1Indicate the alkyl containing 1~5 carbon atom.
4. a kind of method preparing the liquid-crystal compounds containing difluoro-methoxy bridged bond with logical structure shown in formula I, which is characterized in that
Include the following steps：
(1) compound a passes through grignard, suzuki coupling synthesis compounds b；
(2) after the compound b takes hydrogen by force by highly basic, with after two bromine reaction of difluoro compound c；
(3) the compound c obtains final compound under alkaline condition with phenol.
5. method as claimed in claim 4, which is characterized in that the highly basic be butyl lithium, LDA, potassium tert-butoxide, HMDSLi or
Sodium hydrogen.
6. a kind of liquid-crystal composition, which is characterized in that contain difluoro-methoxy bridge including claims 1 to 3 any one of them
The liquid-crystal compounds of key.
7. liquid-crystal composition as claimed in claim 6, which is characterized in that the quality of the liquid-crystal compounds accounts for the liquid crystal group
Close the 1-70% of object gross mass.
8. liquid-crystal composition as claimed in claim 6, which is characterized in that the quality of the liquid-crystal compounds accounts for the liquid crystal group
Close the 3-50% of object gross mass.
9. a kind of application of liquid-crystal composition as claimed in claim 8 in field of liquid crystal.
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| CN201810648363.4A CN108659851A (en) | 2018-06-22 | 2018-06-22 | A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond |
| PCT/CN2018/102613 WO2019242095A1 (en) | 2018-06-22 | 2018-08-28 | Liquid crystal compound containing a difluoromethoxy bridge bond and preparation method and application thereof |
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| CN201810648363.4A CN108659851A (en) | 2018-06-22 | 2018-06-22 | A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond |
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| JP2016175886A (en) * | 2015-03-23 | 2016-10-06 | Jnc株式会社 | Liquid crystal compound having halogenated alkyl, liquid crystal composition, and liquid crystal display element |
| CN107955631A (en) * | 2017-11-22 | 2018-04-24 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108148602A (en) * | 2018-02-09 | 2018-06-12 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108690639A (en) * | 2018-06-22 | 2018-10-23 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
-
2018
- 2018-06-22 CN CN201810648363.4A patent/CN108659851A/en active Pending
- 2018-08-28 WO PCT/CN2018/102613 patent/WO2019242095A1/en active Application Filing
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242860A (en) * | 2013-05-15 | 2013-08-14 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN104342168A (en) * | 2013-08-06 | 2015-02-11 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with good low temperature storage stability and liquid crystal display device |
| CN104371746A (en) * | 2013-08-16 | 2015-02-25 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN104513145A (en) * | 2013-09-29 | 2015-04-15 | 江苏和成新材料有限公司 | 2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound |
| JP2016175886A (en) * | 2015-03-23 | 2016-10-06 | Jnc株式会社 | Liquid crystal compound having halogenated alkyl, liquid crystal composition, and liquid crystal display element |
| CN107955631A (en) * | 2017-11-22 | 2018-04-24 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108148602A (en) * | 2018-02-09 | 2018-06-12 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108690639A (en) * | 2018-06-22 | 2018-10-23 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
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