CN108690636A - A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof - Google Patents
A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof Download PDFInfo
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- 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
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- 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
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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Abstract
The present invention relates to a kind of liquid-crystal compounds of novel 2,3- difluorobenzenes class negative dielectric anisotropic, which has many advantages, such as relatively higher negative dielectric anisotropic, relatively lower rotary viscosity and good liquid crystal intersolubility.The negative dielectric anisotropic of the composition containing the liquid-crystal compounds can be effectively improved, and then improve the response time of liquid crystal display, while having the characteristics that moderate optical anisotropy numerical value, charge conservation rate height, good liquid crystal intersolubility, the performance of low-temperature working effect are outstanding.
Description
Technical field
The invention belongs to liquid-crystal compounds and its application fields, and in particular to a kind of negative dielectric of novel 2,3- difluorobenzenes class is each
Anisotropy compound and the preparation method and application thereof.
Background technology
Liquid crystal material has pole as application of the environmentally conscious materials in the fields such as presentation of information material, organic optoelectronic material
Big researching value and fine application prospect.There are many advantages as novel display material for liquid crystal material, if power consumption is extremely low, drive
Dynamic voltage is low.Simultaneously compared with other materials, also there is small, light-weight, long-life, display to contain much information, without electromagnetism spoke
The advantages that penetrating almost is adapted to the requirement of various presentation of information, especially in TFT-LCD (thin-film transistor technologies) product side
Face.
In the system of tft active matrix, mainly there are TN (Twisted Nematic, twisted-nematic structure) pattern, IPS
(In-Plane Switching, plane conversion) pattern, FFS (Fringe Field Switching, fringe field switching technology)
The main display pattern such as pattern and VA (VerticalAlignment, vertical orientation) pattern.
Currently, TFT-LCD product technologies are ripe, visual angle, resolution ratio, color saturation and brightness etc. are successfully solved
Technical barrier, large scale and small-medium size TFT-LCD displays have gradually occupied the mainstream of flat-panel monitor in respective field
Status.Dynamic menu is shown and is applied, in order to realize that high-quality is shown, eliminates and shows picture ghost and hangover, it is desirable that liquid crystal
Material has response speed quickly, therefore it is required that liquid crystal material has rotary viscosity γ 1 low as possible.In addition, in order to reduce
The energy consumption of liquid crystal display device needs the driving voltage of liquid crystal low as possible, so improving the dielectric anisotropy △ ε of liquid crystal to mixed
Liquid crystal is closed to be of great significance.
Core Feature material of the liquid crystal material as liquid crystal display device, to meet the various performances ginseng of liquid crystal display device
Several requirements adapts to the technological requirement of liquid crystal display device, needs liquid crystal material to have extensive multiple performance parameter, especially
It reduces liquid crystal material rotary viscosity γ 1 and improves the dielectric anisotropy △ ε of liquid crystal material.Performance in order to improve material makes it
New requirement is adapted to, the synthesis of new structure liquid-crystal compounds and the research of structure-performance relation become one of field of liquid crystals
Important process.
Invention content
The first object of the present invention is to provide a kind of liquid-crystal compounds of novel 2,3- difluorobenzenes class negative dielectric anisotropic,
The compound has relatively higher negative dielectric anisotropic, relatively lower rotary viscosity and good liquid crystal intersolubility etc.
Advantage.
Liquid-crystal compounds of the present invention has the structure as shown in general formula I:
In the general formula I, R represents alkyl or alkoxy with 1~12 carbon atom;N represents 0 or 1.
Preferably, in the general formula I, R represents alkyl or alkoxy with 1~7 carbon atom;N represents 0 or 1.
It is further preferred that in the general formula I, R represents the alkyl with 1~7 carbon atom;N represents 0 or 1.
As the preferred forms of the present invention, the liquid-crystal compounds is selected from the one or more of following compound:
The second object of the present invention is to provide the preparation method of the liquid-crystal compounds.
Liquid-crystal compounds synthetic route of the present invention is as follows:
The preparation method of the liquid-crystal compounds specifically includes following steps:
(1)With organolithium reagent carry out metallization reaction, then withReaction, obtains
(2)It is dehydrated under acid catalysis, obtains general structure
(I) compound.
Wherein, R, n in compound involved by each step are opposite with the group that R, n in gained liquid-crystal compounds product are represented
It answers.
Preferably, in the step (1),Organolithium reagent withMolar ratio be 1: 0.9~2.0: 0.9~2.0.Reaction temperature can be -50~-100
DEG C, preferably -60~-70 DEG C.The organolithium reagent is selected from n-BuLi, s-butyl lithium, tert-butyl lithium or n-BuLi and uncle
One or more of the combination of butanol potassium.
It is described in step (1)The preparation side that those skilled in the art are grasped can be used
Method obtains.In the present invention, it is preferred toWith BrCH2CH2F is raw material, in the presence of a base, is passed through
Williamson etherification reactions, obtainIt is further preferred that the alkali is selected from sodium hydroxide, hydrogen
The one or more of potassium oxide, sodium carbonate, potassium carbonate, sodium bicarbonate.The reaction temperature can at 30~150 DEG C, preferably 70~
80℃。
Preferably, in the step (2), the acid can be selected from p-methyl benzenesulfonic acid, potassium acid sulfate, sulfuric acid, hydrochloric acid, acetic acid,
One or more of boron trifluoride ether.Reaction temperature can be at 30~150 DEG C.
It is above-mentionedBrCH2CH2F,Open business way can be passed through
Method known per se synthesizes to obtain in diameter or document.
Synthetic method of the present invention can be related to conventional post-processing if necessary, and the conventional post-processing is specific such as:With
Dichloromethane, ethyl acetate or toluene extraction, liquid separation are washed, dry, vacuum rotary evaporator evaporation, products therefrom decompression
Distillation or recrystallization and/or chromatography purification, you can.
It can be stablized using above-mentioned preparation method, be efficiently obtained liquid-crystal compounds of the present invention.
The third object of the present invention is the composition of liquid-crystal compounds of the protection containing the general formula I.The liquid crystal
The mass percent of compound in the composition is 1~60%, preferably 2~50%, further preferably 3~25%.
The fourth object of the present invention is that the protection liquid-crystal compounds and the composition containing the liquid-crystal compounds exist
The application of field of liquid crystal display, the application preferably in liquid crystal display device.The liquid crystal display device includes but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
2,3- difluorobenzenes class liquid-crystal compounds provided by the present invention introduces a fluorine ethoxy group in the molecular structure, together
When in the introducing cyclohexenyl groups of 2,3- difluorophenyls 4, form the big pi bond of conjugation, negative Jie of liquid-crystal compounds can be significantly improved
Electrical anisotropy, reduces the rotary viscosity of liquid-crystal compounds, while having good thermal stability, chemical stability, optics steady
It is qualitative, and improve its mechanics, dielectric and other multiple performances.The composition containing the liquid-crystal compounds can be effectively improved
Negative dielectric anisotropic, and then improve the response time of liquid crystal display, while having that optical anisotropy numerical value is moderate, charge
The features such as conservation rate height, good liquid crystal intersolubility, outstanding low-temperature working effect performance.
Specific implementation mode
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
The raw material unless otherwise instructed, can be obtained from open commercial sources.
According to the common detection methods of this field, the various performance parameters of liquid-crystal compounds are obtained by linear fit,
In, the concrete meaning of each performance parameter is as follows:
△ n represent optical anisotropy (25 DEG C);△ ε represent dielectric anisotropy (25 DEG C, 1000Hz);γ 1 represents rotation
Turn viscosity (mPa.s, 25 DEG C);Cp represents clearing point.
Embodiment 1
The structural formula of liquid-crystal compounds is:
The synthetic line of prepare compound BYLC-01 is as follows:
It is as follows:
(1) synthesis of compound BYLC-01-1:
65g 2,3- difluorophenols, the fluoro- 1- bromoethanes of 75.6g 2-, 500mlN, N- dimethyl formyls are added in reaction bulb
40g sodium hydroxides are added portionwise in amine under stirring, finish 70-80 DEG C of reaction 5h of temperature control, be quenched instead with 400ml 2M aqueous hydrochloric acid solutions
It answers, carries out conventional post-processing, obtain yellow liquid (compound BYLC-01-1) 84.5g, GC:98.8%, yield 96%;
(2) synthesis of compound BYLC-01-2:
Under nitrogen protection, 17.6g compounds BYLC-01-1,160ml tetrahydrofuran, temperature control -60 are added into reaction bulb
The hexane solution of~-70 DEG C of dropwise addition 0.12mol n-BuLis drips and finishes insulation reaction 1 hour, and temperature control -60~-70 DEG C are added dropwise
The solution of 14g4- propylcyclohexyls ketone and 20ml tetrahydrofurans composition, then returns and warms to room temperature naturally.100ml 2M hydrochloric acid is added
Aqueous solution is acidified, and conventional post-processing is carried out, and revolving solvent obtains yellow liquid (compound BYLC-01-2) 31.6g, GC:
84.3%, yield 100%;
(3) synthesis of compound BYLC-01:
31.6g compounds BYLC-01-2,1g p-methyl benzenesulfonic acid is added into reaction bulb, 200ml toluene is heated to reflux point
Water reacts 6h, and the reaction was complete, carries out conventional post-processing, and through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white solid
(compound BYLC-01):22.0g GC:99.5%, yield:74%.
The structural characterization information of compound BYLC-01 is as follows:
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product is 298.1 (M+);
1H-NMR(400MHz,CDCl3):6.97-6.64(m,2H),5.90-5.66(m,1H),4.88–4.63(m,2H),
4.40–4.20(m,2H),2.04–0.85(m,14H)。
Embodiment 2
Technical solution according to embodiment 1, it is only necessary to the corresponding raw material of simple replacement does not change any substantive operations,
Following liquid-crystal compounds can be synthesized.
Embodiment 3
The structural formula of liquid-crystal compounds is:
The synthetic line of prepare compound BYLC-03 is as follows:
It is as follows:
(1) synthesis of compound BYLC-03-1:
Under nitrogen protection, 17.6g compounds BYLC-01-1,160ml tetrahydrofuran, temperature control -60 are added into reaction bulb
The hexane solution of~-70 DEG C of dropwise addition 0.12mol n-BuLis drips and finishes insulation reaction 1 hour, and temperature control -60~-70 DEG C are added dropwise
The solution of 22.2g4- propyl dicyclohexyl ketone and 30ml tetrahydrofurans composition, then returns and warms to room temperature naturally.100ml 2M are added
Aqueous hydrochloric acid solution is acidified, and conventional post-processing is carried out, and revolving solvent obtains yellow liquid (compound BYLC-03-1) 39.8g,
GC:83.7%, yield 100%;
(2) synthesis of compound BYLC-03:
39.8g compounds BYLC-03-1,2g p-methyl benzenesulfonic acid is added into reaction bulb, 200ml toluene is heated to reflux point
Water reacts 6h, and the reaction was complete, carries out conventional post-processing, and through chromatogram purification, n-hexane elution, ethyl alcohol+toluene Mixed Solvent is tied again
Crystalline substance obtains white solid (compound BYLC-03):27.0g GC:99.8%, yield:71%.
The structural characterization information of compound BYLC-03 is as follows:
Gained white solid BYLC-03 is analyzed using GC-MS, the m/z of product is 380.2 (M+);
1H-NMR(400MHz,CDCl3):6.97-6.64(m,2H),5.90-5.66(m,1H),4.88–4.63(m,2H),
4.40–4.20(m,2H),2.05–0.84(m,24H)。
Embodiment 4
Technical solution according to embodiment 3, it is only necessary to the corresponding raw material of simple replacement does not change any substantive operations,
Following liquid-crystal compounds can be synthesized.
Experimental example 1
By the compound BYLC-01 and comparative example 1 (known common another like liquid-crystal compounds) obtained by embodiment 1
Liquid-crystal compounds performance parameter data carry out comparison arrangement, testing result is as shown in table 1:
Table 1:The performance test results of liquid-crystal compounds
By the testing result of table 1, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
Structure compound is compared, and liquid-crystal compounds provided by the invention has higher negative dielectric anisotropic, lower rotary viscosity good
Good liquid crystal intersolubility, the performance of low-temperature working effect is outstanding, can effectively improve the negative dielectric anisotropic of liquid-crystal composition, changes
The kind response time.
Experimental example 2
By the compound BYLC-03 and comparative example 2 (known common another like liquid-crystal compounds) obtained by embodiment 3
Liquid-crystal compounds performance parameter data carry out comparison arrangement, testing result is as shown in table 2:
Table 2:The performance test results of liquid-crystal compounds
By the testing result of table 2, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
Structure compound is compared, and liquid-crystal compounds provided by the invention has higher negative dielectric anisotropic, lower rotary viscosity good
Good liquid crystal intersolubility, the performance of low-temperature working effect is outstanding, can effectively improve the negative dielectric anisotropic of liquid-crystal composition, changes
The kind response time.
Although above having used general explanation, specific implementation mode and experiment, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. one kind 2, the liquid-crystal compounds of 3- difluorobenzene class negative dielectric anisotropics, which is characterized in that have and tied as shown in general formula I
Structure:
In the general formula I, R represents alkyl or alkoxy with 1~12 carbon atom;N represents 0 or 1.
2. the liquid-crystal compounds of 2,3- difluorobenzenes class negative dielectric anisotropic according to claim 1, which is characterized in that institute
It states in general formula I, R represents alkyl or alkoxy with 1~7 carbon atom;Preferably, R, which is represented, has 1~7 carbon atom
Alkyl.
3. the liquid-crystal compounds of 2,3- difluorobenzenes class negative dielectric anisotropic according to claim 1, which is characterized in that institute
It states liquid-crystal compounds and is selected from the one or more of following compound:
4. the preparation method of any liquid-crystal compounds of claim 1-3, which is characterized in that include the following steps:
(1)With organolithium reagent carry out metallization reaction, then withInstead
It answers, obtains
(2)It is dehydrated under acid catalysis, obtains general structure (I)
Compound;
Wherein, R, n are defined identical as claim 1.
5. preparation method according to claim 4, which is characterized in that in the step (1), reaction temperature be -50~-
100 DEG C, preferably -60~-70 DEG C.
6. preparation method according to claim 4, which is characterized in that in the step (1), the organolithium reagent is selected from
N-BuLi, s-butyl lithium, tert-butyl lithium or n-BuLi one or more of are combined with potassium tert-butoxide.
7. preparation method according to claim 4, which is characterized in that described in the step (1)
Be withWith BrCH2CH2F is raw material, in the presence of a base, is obtained by Williamson etherification reactions.
8. preparation method according to claim 4, which is characterized in that in the step (2), the acid is selected to toluene sulphur
One or more of acid, potassium acid sulfate, sulfuric acid, hydrochloric acid, acetic acid, boron trifluoride ether.
9. a kind of liquid-crystal composition, which is characterized in that the liquid-crystal compounds containing any general formula Is of claim 1-3,
The mass percent of the liquid-crystal compounds in the composition is 1~60%, preferably 2~50%, further preferably 3
~25%.
10. liquid-crystal composition is in field of liquid crystal display described in any liquid-crystal compounds of claim 1-3 or claim 9
Using the application preferably in liquid crystal display device;The liquid crystal display device be more preferably TN, ADS, VA, PSVA,
FFS or IPS liquid crystal displays.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110373210A (en) * | 2019-08-07 | 2019-10-25 | 西安近代化学研究所 | A kind of liquid-crystal compounds and combinations thereof containing difluoroethoxy |
| CN111718726A (en) * | 2019-03-21 | 2020-09-29 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof |
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|---|---|---|---|---|
| JPH024723A (en) * | 1988-03-10 | 1990-01-09 | Merck Patent Gmbh | Cyclohexene derivative |
| EP1903090A2 (en) * | 2006-09-06 | 2008-03-26 | Chisso Corporation | Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device |
| CN101490212A (en) * | 2006-07-19 | 2009-07-22 | 默克专利股份有限公司 | Liquid crystalline medium |
| CN101724407A (en) * | 2008-10-30 | 2010-06-09 | 默克专利股份有限公司 | Liquid-crystalline medium and liquid crystal display |
-
2017
- 2017-04-06 CN CN201710221064.8A patent/CN108690636B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH024723A (en) * | 1988-03-10 | 1990-01-09 | Merck Patent Gmbh | Cyclohexene derivative |
| CN101490212A (en) * | 2006-07-19 | 2009-07-22 | 默克专利股份有限公司 | Liquid crystalline medium |
| EP1903090A2 (en) * | 2006-09-06 | 2008-03-26 | Chisso Corporation | Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device |
| CN101724407A (en) * | 2008-10-30 | 2010-06-09 | 默克专利股份有限公司 | Liquid-crystalline medium and liquid crystal display |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111718726A (en) * | 2019-03-21 | 2020-09-29 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof |
| CN111718726B (en) * | 2019-03-21 | 2022-02-22 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof |
| CN110373210A (en) * | 2019-08-07 | 2019-10-25 | 西安近代化学研究所 | A kind of liquid-crystal compounds and combinations thereof containing difluoroethoxy |
| CN110373210B (en) * | 2019-08-07 | 2021-12-21 | 西安近代化学研究所 | Difluoroethoxy-containing liquid crystal compound and composition thereof |
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