CN107057718A - A kind of oxygen difluoro methylene liquid crystal containing dicyclohexyl and synthetic method - Google Patents
A kind of oxygen difluoro methylene liquid crystal containing dicyclohexyl and synthetic method Download PDFInfo
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- CN107057718A CN107057718A CN201710278875.1A CN201710278875A CN107057718A CN 107057718 A CN107057718 A CN 107057718A CN 201710278875 A CN201710278875 A CN 201710278875A CN 107057718 A CN107057718 A CN 107057718A
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- liquid crystal
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- difluoro methylene
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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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
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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
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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
- C09K19/08—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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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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
- 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
Abstract
The present invention relates to a kind of oxygen difluoro methylene liquid crystal containing dicyclohexyl and synthetic method, being somebody's turn to do the oxygen difluoro methylene liquid crystal containing dicyclohexyl has following structural formula：
Description
Technical field
Hold CF the present invention relates to one kind2The fluorine-containing similar liquid-crystal compounds of superelevation of O bridged bonds, they can be used as sound at a high speed
Should and low voltage threshold 1 TFT liquid crystal compound key components, 4- [4 ＇-alkyl (trans, anti-form-1,1 ＇-bis- alkane oneself
Base)] -2,6- difluorophenyls }-(the fluoro- 4- 4-trifluoromethylphenopendants of 3-) difluoromethane.
Background technology
In order that display device can be used in a variety of weather conditions, molecule is allowed for non-including room temperature
Constant width temperature range forms stable nematic phase.Therefore, liquid crystal molecule must have low fusing point and high clearing point.In order to realize
Quick response, molecule must have the low commercial Application shown for liquid crystal flat-panel, it is desirable to which liquid crystal molecule must have
Specific viscosity.
The big bigger viscosity of liquid crystal polarity of dielectric anisotropy is also bigger.Therefore the requirement to liquid crystal Low threshold and response are fast
Degree is conflicting soon.In order to solve this problem, bridged bond-CF2O- is introduced in liquid crystal molecule, in identical △ ε bar
Under part, the liquid crystal compared with low-viscosity can be obtained.The reason for producing this phenomenon is between the dipole moment of molecule and molecular long axis
The difference of angle is caused.To the molecule with same viscosity, if introducing CF2O bridged bonds, then angle diminish, △ ε become big.
The researcher of German Merck companies reported that such had the synthesis of bridged bond compound first in 1989
(E.Bartmann,etal.,(Merck KGaA),DE-A4006921,1989).1990s, such liquid-crystal compounds was obtained
Systematic research (A1 of EP 0844229) is arrived.Research finds some-CF2O- liquid crystal not only has low-viscosity but also with good
Good dissolubility.From (DE 19531165A1), Japanese Chisso companies after nineteen ninety-five Merck company's application patent of invention
Start application patent of invention (WO 96 11995).
There is CF in design2During O bridged bond liquid crystal molecules, big △ ε and low viscosity are not only taken into account, and to keep away
Exempt from smectic phase (S) occur.A host of facts confirm that three-ring system often occurs without liquid crystalline phase, and nematic phase can occur in tetracyclic ring system,
But the viscosity of the latter is greatly increased than three-ring system.Dielectric anisotropy is big and viscosity is low for meeting of using now
Molecule, even if without liquid crystalline phase, but after being mixed with nematic liquid crystal mixture, the work(of liquid crystal molecule is similarly presented
Energy.In that case, also broadly they are called " to maintain CF in document2The liquid crystal of O bridged bonds ".
Goal of the invention
The purpose of the present invention be on the basis of a large amount of accumulation that fluorinated liquid crystal is studied, initiative it is new there is Chinese fluorine chemistry
Feature " maintains CF2O bridged bonds liquid crystal ", a kind of oxygen difluoro methylene liquid crystal containing dicyclohexyl and synthetic method.Therefore,
4- alkyl bicyclics hexyl is introduced into molecule, to the purpose for the viscosity for reaching attenuating.It was found that such liquid crystal is as a small amount of
Doping agent is used, and can greatly improve response speed.In the present invention, the super fluorination that a class contains 8 fluorine atoms is successfully synthesized
" maintaining CH2O bridged bonds liquid crystal ".Test result points out that they nematic phase only occur, therefore can prepare mixed liquid crystal material
Used during material as particular components.
The oxygen difluoro methylene liquid crystal containing dicyclohexyl of the present invention has following structural formula：
Wherein, n=2~10.Prioritizing selection n=2~6, especially n=3~5.
The reaction equation of oxygen difluoro methylene liquid crystal of the synthesis containing dicyclohexyl of the present invention is as follows：
Wherein, a:Magnesium, tetrahydrofuran, 50 DEG C；b：Alkyl bicyclic hexyl ketone (n=2~10), 50 DEG C, tetrahydrofuran；c：First
Benzene, a hydration p-methyl benzenesulfonic acid, is heated to reflux；d：Hydrogen, palladium carbon；e：Difluorodibromomethane, tetrahydrofuran, n-BuLi ,-
70℃；f:The fluoro- 4- trifloro methyl phenols of 3-, tetra-n-butyl ammonium bromide, potassium carbonate, DMF, 80 DEG C.The present invention
Oxygen difluoro methylene liquid crystal of the synthesis containing dicyclohexyl method, description can be simplified：
Oxygen difluoro methylene liquid crystal containing dicyclohexyl can be named as difluoro { 4- ([4'-H again2n+1Cn- trans
1,1'- dicyclohexyl] -4- bases) 3,5- difluorophenyls } the fluoro- 4- benzotrifluorides epoxide methane of 3-, for example preceding institute of compound A7, wherein n
State.
Under 60 DEG C~reflux temperature and in organic solvent, 4 ([4'- n-propyls-trans 1,1'- dicyclohexyls] -4-
Base) the fluoro- 4- trifloro methyl phenols of 2,6- difluorophenyls-difluoro bromomethane A6,3- react 1~4 hour, obtain purpose product.Institute
4 ([4'- n-propyls-trans 1,1'- dicyclohexyls] -4- bases) 2, the 6- difluorophenyls-difluoro bromomethane A6,3- stated are fluoro-
The mol ratio of 4- trifloro methyl phenols is 1:0.2~1:1:~2:1~2, it is 1 to recommend mol ratio:0.3~0.6:1:1.5:1~
1.5。
Heretofore described organic solvent can be that for ethanol, tetrahydrofuran, DMF isopolarity has
Machine solvent.
The method of the present invention advises carrying out under inert gas shielding.
The method of the present invention can be quenched using saturation ammonium chloride solution.Reaction solution can be extracted with organic solvent,
Such as saturated ammonium chloride solution and ethyl acetate are extracted, and organic phase is washed with the saturated common salt aqueous solution again, are dried, are spin-dried for, will be thick
Product is used column chromatography, and the method such as recrystallization carries out purification process.
Not only method is easy by the present invention, and the oxygen difluoro methylene liquid crystal containing dicyclohexyl of the present invention, test
As a result only there is nematic phase in them, therefore can be used when preparing mixed liquid crystal material as particular components.
Embodiment
By following embodiments it will be further appreciated that present invention.
1) [1'- hydroxyls -4'- (trans 4 "-n-propyl cyclohexyl) cyclohexyl] -3,5- difluorobenzenes, compound A-13 (n=3)
Synthesis：
In the four-hole boiling flask of a 500ml dried, nitrogen protection is lower to add Mg (7.70g；0.32mol), it is subsequently added
The tetrahydrofuran of 50ml drying, 1, the 2- Bromofumes for adding 1~3 drop enter line activating, by 3,5- difluoro bromobenzenes after activation
(50g, 0.26mol) is dissolved in the tetrahydrofuran of 120ml drying, is slowly dropped in system, and this reaction system is at 40 DEG C
~50 DEG C are reacted 2 hours, and (71g is added after reactive magnesium is complete；Propyl group dicyclohexyl ketone 0.32mol), is slowly dropped into, reaction
Mixed liquor continues to react 2 hours at 40 DEG C~50 DEG C, and TLC tracking reactions add water and are quenched after completely, reaction solution acetic acid second
Ester is extracted, and is dried with anhydrous magnesium sulfate, is filtered to remove magnesium sulfate, and rotary evaporation removes solvent, obtains light yellow liquid
Body 80g, yield is 91.4%, and purity is 87%.
2) [4'- (4 "-trans-n-propyl cyclohexyl)-cyclohexenyl group] -1 base } -3,5- difluorobenzenes, compound A4 (n=
3) synthesis
Compound A2 (n=3) (98.6g, 0.29mol) is dissolved in 150ml toluene, poured into 500ml single-necked flasks, is added
(5.6g, 0.029mol) one is hydrated p-methyl benzenesulfonic acid, is heated with stirring to backflow, and moisture, sampling analysis, reaction are separated with water knockout drum
After completely, room temperature being cooled to, adding 100ml water, split-phase separates organic layer, with 40ml toluene aqueous phase extracteds, merge organic phase,
Saturated common salt water washing is used again three times, anhydrous magnesium sulfate is dried, and filtering, rotary evaporation removes solvent, is then entered again with petroleum ether
Row column chromatography for separation, obtains white solid 74.1g, and yield is 80%, and purity is 99%
3) 4- [4'- bromo-trans anti-form-1s, 1'- dicyclohexyls] -3,5- difluorobenzenes, the synthesis of compound A-45 (n=3)
High pressure is installed with 15 grams of Pd/C. of 200ml toluene dissolved compound A4 (n=3) (74.1g, 0.233mol) and addition
Kettle leads to N2Examine air-tightness, 0.5MPa pressure keep 120 minutes it is constant, bleed off N2, kettle vacuumizes, is repeated 2 times, and is passed through H2Pressure
0.5MPa is reached, if 35 DEG C of temperature, is reacted 24 hours, sampling detection, the complete suction filtrations product removing Pd/C of reaction, rotary evaporation,
Product 70g is obtained, yield is 93.8%, and purity is 98%.
4) 4 ([4'- n-propyls-trans 1,1'- dicyclohexyls] -4- bases) 2,6- difluorophenyls-difluoro bromomethane, change
Compound A6 (n=3) synthesis
In the four-hole boiling flask of a 500ml dried, under nitrogen protection, by (24g, 0.075mol) compound A-45 (n=3)
It is dissolved in the THF of 200ml dryings and is cooled to -70 DEG C, the positive fourth of (57ml, 0.162mol) is slowly added dropwise into above-mentioned solution
Base lithium (1.6mol/L), this mixed solution continues stirring 2 hours at the temperature disclosed above, is slowly added to (24g, 0.141mol)
CF2Br2, and it is warming up to -60 DEG C, reaction mixture continues to react 1 hour, sampling detection, after reaction completely, plus saturated ammonium chloride
Solution is quenched.Reaction solution is extracted with saturated ammonium chloride solution and ethyl acetate, and organic phase is washed with the saturated common salt aqueous solution again
Twice, organic phase is dried with anhydrous magnesium sulfate, filtering, is spin-dried for, and obtains crude product and crude product is carried out into column chromatography point with petroleum ether again
From 32.9g pale yellow oils, yield：97.9%, purity is 25%.
5) difluoro { 4- ([4' n-propyls-trans 1,1'- dicyclohexyls] -4- bases) 3,5- difluorophenyls } the fluoro- 4- of 3-
Benzotrifluoride epoxide methane, compound A7 (n=3) synthesis
In the four-hole boiling flask of a 500ml dried, nitrogen protection is lower to add (32,9g, 0.073mol) purity 25%
A6 (n=3), the fluoro- 4- trifloro methyl phenols of 3- of (7,9g, 0.04mol), the K of (15.4g, 0.11mol)2CO3,(35.2g,
Tetra-n-butyl ammonium bromide (C 0.109mol)16H36), NBr 200ml N,N-dimethylformamide, reaction mixing are subsequently added
Liquid reacts stirring 4 hours under the conditions of 80 DEG C, and sampling detection after reaction completely, is quenched with saturation ammonium chloride solution, reacted
Liquid is extracted with saturated ammonium chloride solution and ethyl acetate, and organic phase is washed twice with the saturated common salt aqueous solution again, and organic phase is used
Anhydrous magnesium sulfate is dried, and is spin-dried for, is obtained crude yellow oil, crude product is carried out into column chromatography for separation, anhydrous second with petroleum ether
Alcohol is recrystallized, and obtains 2.6g white solids, purity 99.6%, yield：16%
Fusing point：94 DEG C, clearing point：157.4℃.
Claims (7)
1. the oxygen difluoro methylene liquid crystal containing dicyclohexyl has following structural formula：
Wherein, n=2~10.
2. the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that wherein n=2~6.
3. a kind of synthetic method of the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that
Obtained by following methods：
Under 60 DEG C~reflux temperature and in polar organic solvent, 4 ([4'- n-propyls-trans 1,1'- dicyclohexyls] -4-
Base) the fluoro- 4- trifloro methyl phenols of 2,6- difluorophenyls-difluoro bromomethane A6,3- react 1~4 hour；4 described ([4'- positive third
Base-trans 1,1'- dicyclohexyls] -4- bases) the fluoro- 4- trifloro methyl phenols of 2,6- difluorophenyls-difluoro bromomethane A6,3-
Mol ratio be 1:0.2~1:1:~2:1~2.
4. a kind of synthetic method of the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that
Described polar organic solvent is ethanol, tetrahydrofuran, DMF.
5. a kind of synthetic method of the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that
Reaction is carried out under inert gas shielding.
6. a kind of synthetic method of the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that
It is quenched using saturation ammonium chloride solution.
7. a kind of synthetic method of the oxygen difluoro methylene liquid crystal as claimed in claim 1 containing dicyclohexyl, it is characterized in that
Reaction solution is extracted with organic solvent, and organic phase is washed with the saturated common salt aqueous solution again, is dried, is spin-dried for, column chromatography for separation or recrystallization
Carry out purification process.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1255475A (en) * | 1998-09-28 | 2000-06-07 | 智索股份有限公司 | Benzene derivative and its prepn. method |
| EP1365001A1 (en) * | 2002-05-24 | 2003-11-26 | MERCK PATENT GmbH | Liquid crystalline medium |
| US20040135120A1 (en) * | 2002-12-04 | 2004-07-15 | Yoshitaka Tomi | Liquid crystal composition and liquid crystal display element |
| US20140203209A1 (en) * | 2013-01-21 | 2014-07-24 | Jnc Petrochemical Corporation | Compound having 3,3,3-trifluoro-1-propenyloxy, liquid crystal composition and liquid crystal display device |
| CN106244169A (en) * | 2016-07-29 | 2016-12-21 | 福建省邵武市永晶化工有限公司 | Three rings surpass fluorine liquid-crystal compounds, synthetic method and application |
| CN106244168A (en) * | 2016-07-19 | 2016-12-21 | 福建永晶科技有限公司 | Fluorinated liquid crystal containing difluoro-methoxy bridged bond and polyfluoro xenyl and combinations thereof thing |
| US20170009137A1 (en) * | 2015-07-07 | 2017-01-12 | Jnc Corporation | Liquid crystal compound, liquid crystal composition and liquid crystal display device |
-
2017
- 2017-04-25 CN CN201710278875.1A patent/CN107057718A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1255475A (en) * | 1998-09-28 | 2000-06-07 | 智索股份有限公司 | Benzene derivative and its prepn. method |
| EP1365001A1 (en) * | 2002-05-24 | 2003-11-26 | MERCK PATENT GmbH | Liquid crystalline medium |
| US20040135120A1 (en) * | 2002-12-04 | 2004-07-15 | Yoshitaka Tomi | Liquid crystal composition and liquid crystal display element |
| US20140203209A1 (en) * | 2013-01-21 | 2014-07-24 | Jnc Petrochemical Corporation | Compound having 3,3,3-trifluoro-1-propenyloxy, liquid crystal composition and liquid crystal display device |
| US20170009137A1 (en) * | 2015-07-07 | 2017-01-12 | Jnc Corporation | Liquid crystal compound, liquid crystal composition and liquid crystal display device |
| CN106244168A (en) * | 2016-07-19 | 2016-12-21 | 福建永晶科技有限公司 | Fluorinated liquid crystal containing difluoro-methoxy bridged bond and polyfluoro xenyl and combinations thereof thing |
| CN106244169A (en) * | 2016-07-29 | 2016-12-21 | 福建省邵武市永晶化工有限公司 | Three rings surpass fluorine liquid-crystal compounds, synthetic method and application |
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Address after: 354003 Jinling Road, Jintong Industrial Park, Shaowu, Fujian Province, No. 6 Applicant after: Fujian permanent crystal Polytron Technologies Inc Address before: 354001 Nanping Province, Shaowu City, sun mouth new ammonia Road, No. 18 Applicant before: Fujian forever Technology Co., Ltd. |
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Application publication date: 20170818 |