CN106398717B - A kind of epoxypentyl class liquid-crystal compounds and preparation method and application - Google Patents
A kind of epoxypentyl class liquid-crystal compounds and preparation method and application Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 99
- 150000001875 compounds Chemical class 0.000 title claims abstract description 95
- 238000002360 preparation method Methods 0.000 title claims description 17
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- -1 cyclohexylidenes Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000003153 chemical reaction reagent Substances 0.000 claims description 18
- 125000001979 organolithium group Chemical group 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 6
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical group [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 5
- 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 5
- 241001614291 Anoplistes Species 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000001465 metallisation Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 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
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 14
- 230000004044 response Effects 0.000 abstract description 8
- 239000000243 solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000012805 post-processing Methods 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 0 Cc(c1c2OC(*)CC1)c(*)c(F)c2F Chemical compound Cc(c1c2OC(*)CC1)c(*)c(F)c2F 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000009413 insulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WPWONWKAJHOHRJ-MAGNIPBMSA-N CCCC(CC1)Oc2c1c(C)c(C(CC1)CCC1[C@@H]1OCCC1)c(F)c2F Chemical compound CCCC(CC1)Oc2c1c(C)c(C(CC1)CCC1[C@@H]1OCCC1)c(F)c2F WPWONWKAJHOHRJ-MAGNIPBMSA-N 0.000 description 1
- JIUSWCUMAWTOPO-UHFFFAOYSA-N C[O]=C(CC1)CCC1C1OCCC1 Chemical compound C[O]=C(CC1)CCC1C1OCCC1 JIUSWCUMAWTOPO-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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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
-
- 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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- 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
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The present invention relates to liquid crystal material fields, and in particular to and a kind of epoxypentyl class liquid-crystal compounds has the structure as shown in general formula I, wherein, R represents alkyl or alkoxy with 1 12 carbon atoms；Ring A represents 1,4 phenylenes that 1,4 phenylenes, 1,4 cyclohexylidenes or 14 hydrogen atoms are replaced by fluorine atoms；Ring B represents 1,4 phenylenes that 1,4 phenylenes, 1,4 cyclohexylidenes, 1,4 cyclohexadienylidenes or 14 hydrogen atoms are each independently replaced by fluorine atoms；M is 0,1 or 2.Liquid-crystal compounds provided by the invention is moderate with higher negative dielectric anisotropic, rotary viscosity γ 1, good low temperature intersolubility and higher clearing point performance.Herein described compound, which is particularly applicable in, can improve the dielectric anisotropy △ ε of liquid-crystal composition in the liquid-crystal composition of conventional system, relatively low rotary viscosity γ 1 and appropriate refractive anisotrop △ n is kept simultaneously, gained liquid-crystal composition has the characteristics that significant quick response and low voltage drive feature.
Description
Technical field
The invention belongs to liquid-crystal compounds and its application fields, are related to a kind of novel epoxy amyl class negative dielectric anisotropic
Liquid-crystal compounds and preparation method and application.
Technical background
Liquid crystal display device development in recent years is more and more rapider, also develops different type, such as vehicle-mounted small-sized liquid crystal display
Device, portable liquid crystal device, ultrathin liquid crystal display device etc., this field exploitation is making progress, with TV
Exemplified by, its main feature is that it is light-weight, take up space small, conveniently moving, also have subnotebook PC, palm PC, mobile phone etc..
Application of the liquid crystal material as environmentally conscious materials in the fields such as presentation of information material, organic optoelectronic material has pole
Big researching value and fine application prospect, at present, TFT-LCD product technologies are ripe, successfully solve visual angle, divide
The technical barriers such as resolution, color saturation and brightness, large scale and small-medium size TFT-LCD displays are gradual in respective field
Occupy the dominant position of flat-panel monitor.But the requirement to display technology is constantly improving always, it is desirable that liquid crystal display
Realize faster response, reduce driving voltage to reduce power consumption etc., also require liquid crystal material have low voltage drive,
Quick response, wide temperature range and good low-temperature stability.
Liquid crystal material in itself plays an important role to the performance for improving liquid crystal display, especially reduces liquid crystal material rotation
Turn viscosity and improve the dielectric anisotropy △ ε of liquid crystal material.It is new in order to which the performance for improving material adapts it to new requirement
The synthesis of structure liquid-crystal compounds and the research of structure-performance relation become an important process of field of liquid crystals.
The content of the invention
The first object of the present invention is to provide a kind of liquid-crystal compounds of novel epoxy amyl class negative dielectric anisotropic, should
Compound has many advantages, such as higher negative dielectric anisotropic, good liquid crystal intersolubility, relatively low rotary viscosity, these are just
It is that improvement liquid crystal material is required, there is important application value.
Liquid-crystal compounds of the present invention has such as lower structure：
Wherein, R represents alkyl or alkoxy with 1-12 carbon atom；Ring A represents 1,4- phenylenes, 1,4- Asias hexamethylene
The 1,4- phenylenes that base or 1-4 hydrogen atom are replaced by fluorine atoms；Ring B represents that 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- are sub-
The 1,4- phenylenes that cyclohexenyl group or 1-4 hydrogen atom are replaced by fluorine atoms；
M is 0,1 or 2.
Preferably, in general formula I, R represents alkyl or alkoxy with 1-5 carbon atom, and ring A represents Isosorbide-5-Nitrae-Asia benzene
The 1,4- phenylenes that base, 1,4- cyclohexylidenes or 1-4 hydrogen atom are replaced by fluorine atoms；Ring B represents that 1,4- phenylenes, 1,4- are sub-
The 1,4- phenylenes that cyclohexyl, 1,4- cyclohexadienylidenes or 1-4 hydrogen atom are replaced by fluorine atoms；
M is 0,1 or 2.
It is highly preferred that in general formula I, R represents alkyl or alkoxy with 1-5 carbon atom, and ring A represents Isosorbide-5-Nitrae-Asia benzene
The 1,4- phenylenes that base, 1,4- cyclohexylidenes or 1-2 hydrogen atom are replaced by fluorine atoms；Ring B represents that 1,4- phenylenes, 1,4- are sub-
The 1,4- phenylenes that cyclohexyl, 1,4- cyclohexadienylidenes or 1-2 hydrogen atom are replaced by fluorine atoms；M is 0,1 or 2.
As further preferred technical solution, the liquid-crystal compounds is selected from one kind of following compound：
R represents alkyl or alkoxy with 1-5 carbon atom in above-mentioned chemical combination I-1~I-25；More preferable R expressions have
The alkyl of 2-4 carbon atom.
As the preferred forms of the present invention, the liquid-crystal compounds is selected from one kind of following compound：
The second object of the present invention is to provide the preparation method of the liquid-crystal compounds.
The preparation of liquid-crystal compounds of the present invention according to the difference of ring B, selects different synthetic routes.
As a kind of technical solution, when ring B is Isosorbide-5-Nitrae-Asia benzene that Isosorbide-5-Nitrae-phenylene or 1-4 hydrogen atom are replaced by fluorine atoms
During base, synthetic route is as follows：
Specifically include following steps：
(1)It reacts with organolithium reagent, then is reacted with borate, obtained
(2) withWithFor raw material, pass through Suzuki
Reaction, obtains
Wherein, R, m in R, m in compound involved by each step, ring A and gained liquid-crystal compounds product (i.e. general formula I),
The group that ring A is represented is corresponding.
In step 1) described in the above method,The molar ratio of organolithium reagent and borate is 1:
1.0~4.0: 1.0~4.0, reaction temperature -50~-100 DEG C；
Wherein, the one kind of the organolithium reagent in s-butyl lithium, tert-butyl lithium or n-BuLi and potassium tert-butoxide
Or several, the one kind of the borate in trimethylborate, three isobutyl ester of triisopropyl borate ester, butyl borate or boric acid
It is or several.
In the step 2),WithFeed intake
Molar ratio is 1: 0.9~1.2,60~120 DEG C of reaction temperature；
As another technical solution, when ring B is Isosorbide-5-Nitrae-cyclohexylidene, i.e., described liquid-crystal compounds structure such as general formula
When shown in III,
Its synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then with
Reaction, obtains
(2)By with boron trifluoride ether, triethyl group silicon
Alkane reacts, and obtains
Wherein, R, m in R, m in compound involved by each step, ring A and gained liquid-crystal compounds product (i.e. general formula I),
The group that ring A is represented is corresponding.
In step 1) described in the above method,Organolithium reagent with
Molar ratio be 1.0~4.0：1.0~4.0: 1, reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is selected from one or more of s-butyl lithium, tert-butyl lithium or n-BuLi.
In the step 2),
Boron trifluoride ether and triethylsilane feed intake mole
Than for 1: 0.5~3.0：0.5~3.0, reaction temperature -20~-100 DEG C；
As the third technical solution, when ring B is Isosorbide-5-Nitrae-cyclohexadienylidene, i.e., described liquid-crystal compounds structure such as general formula
When shown in IV,
Its synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then with
Reaction, obtains
(2)It is dehydrated, obtains under acid catalysis
Wherein, R, m in R, m in compound involved by each step, ring A and gained liquid-crystal compounds product (i.e. general formula I),
The group that ring A is represented is corresponding.
In step 1) described in the above method,Organolithium reagent,
Molar ratio be 1.0~4.0：1.0~4.0: 1, reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is selected from one or more of s-butyl lithium, tert-butyl lithium or n-BuLi.
In the step 2),It is with sour molar ratio
1: 0.1~0.2,50~120 DEG C of reaction temperature；
Wherein, the acid is selected from one or more of hydrochloric acid, sulfuric acid, formic acid, acetic acid, p-methyl benzenesulfonic acid, potassium acid sulfate,
Preferably p-methyl benzenesulfonic acid.
Method of the present invention, can be related to conventional post processing if necessary, and the conventional post processing is specific such as：Use dichloro
Methane, ethyl acetate or toluene extraction, liquid separation are washed, dry, vacuum rotary evaporator evaporation, products therefrom vacuum distillation
Or recrystallization and/or chromatography purify, 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 composition of the protection containing the liquid-crystal compounds.The liquid-crystal compounds is combining
Mass percent in object is 1~60%, is preferably 3~50%, further preferably 5~25%.
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 is included but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.The liquid-crystal compounds is used or containing the LCD compound
The composition of object has high negative dielectric anisotropic, and rotary viscosity is low, so as to effectively reduce driving voltage, improves liquid crystal
The response speed of display device, while have the characteristics that optical anisotropy numerical value is moderate, charge conservation rate is high.
Specific embodiment
Following embodiment is not limited to the scope of the present invention for illustrating 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).
Embodiment 1
The structural formula for the liquid-crystal compounds that the present embodiment is provided is：
The synthetic line of prepare compound LC-01 is as follows：
It is as follows：
(1) synthesis of compound L C-01-1：
Under nitrogen protection, added in into reaction bulb bis- fluoro- 5- methyl chroman (0.10mol) of 22.6g 2- propyl -7,8- and
The hexane solution of 0.12mol n-BuLis is added dropwise in 320ml tetrahydrofurans, temperature control -75~-85 DEG C, and it is small to drip complete insulation reaction 1
When, the solution of 16.8g4- tetrahydrofuran bases cyclohexanone (0.1mol) and 60ml tetrahydrofurans composition is added dropwise in temperature control -75~-85 DEG C,
Then rise again naturally to -30 DEG C.It adds in 200ml water quenchings to go out reaction, carries out routine post processing, obtain light yellow liquid (compound
LC-01-1) 37.8g, HPLC：93.8%, yield 96.0%.
(2) synthesis of compound L C-01：
Under nitrogen protection, 37.8g compound Ls C-01-1 (0.096mol) and 170ml dichloromethane are added in into reaction bulb,
10.0g triethylsilanes (0.08mol) are added dropwise in temperature control -70~-80 DEG C, when the complete insulation reaction 0.5 of drop is small, temperature control -70~-80 DEG C
12.0g boron trifluoride ether (0.08mol) is added dropwise, then rises again naturally to -20 DEG C.It adds in 200ml water quenchings to go out reaction, carry out often
Rule post processing, obtains white solid (compound L C-01) 27.6g, GC：99.8%, yield 76%；
Gained white solid LC-01 is analyzed using GC-MS, the m/z of product is 378.2 (M+).
1H-NMR(300MHz,CDCl3):0.90-2.00 (m, 22H), 2.30-3.80 (m, 10H).
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 provided in this embodiment is：
The synthetic line of prepare compound LC-02 is as follows：
It is as follows：
(1) synthesis of compound L C-02-1：
Under nitrogen protection, added in into reaction bulb bis- fluoro- 5- methyl chroman (0.1mol) of 21.2g 2- ethyls -7,8- and
The hexane solution of 0.12mol n-BuLis is added dropwise in 250ml tetrahydrofurans, temperature control -75~-85 DEG C, and it is small to drip complete insulation reaction 1
When, temperature control -75~-85 DEG C be added dropwise 25.0g 4- tetrahydrofuran bases bicyclohexanones (0.1mol) and 60ml tetrahydrofurans form it is molten
Then liquid is risen again naturally to -30 DEG C.It adds in 200ml water quenchings to go out reaction, carries out routine post processing, obtain light yellow liquid (chemical combination
Object LC-02-1) 42.3g, HPLC：96.6%, yield 91.6%；
(2) synthesis of compound L C-02：
42.3g LC-02-1 (0.091mol), 0.15mol p-methyl benzenesulfonic acid, bis- uncle of 0.2g 2,6- are added in into reaction bulb
Butyl paracresol and 300ml toluene, when 110 DEG C of reactions 6 of temperature control are small.Conventional post processing is carried out, obtains white solid (compound
LC-02) 28.3g, GC：99.8%, yield 70%；
Gained white solid LC-02 is analyzed using GC-MS, the m/z of product is 444.2 (M+).
1H-NMR(300MHz,CDCl3):0.95-2.60 (m, 33H), 3.50-3.80 (m, 4H), 5.60-5.90 (m, 1H).
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.
Embodiment 5
The structural formula of liquid-crystal compounds provided in this embodiment is：
The synthetic line of prepare compound LC-03 is as follows：
It is as follows：
(1) synthesis of compound L C-03-1：
Under nitrogen protection, the addition 22.6g 2- propyl 7 into reaction bulb, bis- fluoro- 5- methyl chromans (0.1mol) of 8-,
The hexane solution of 0.12mol n-BuLis is added dropwise in 150ml tetrahydrofurans, temperature control -70~-80 DEG C, and it is small to drip complete insulation reaction 1
When, 15.6g trimethylborates (0.15mol) are added dropwise in temperature control -70~-80 DEG C, then rise again naturally to -30 DEG C.Add in 2M hydrochloric acid
Aqueous solution 300ml is acidified, and carries out conventional post processing, and petroleum ether is recrystallized to give light yellow solid (compound L C-03-1)
24.6g HPLC：99.1%, yield 91%；
(2) synthesis of compound L C-03：
Under nitrogen protection, 24.6g compound Ls C-03-1 (0.091mol), 20.6g compounds 4- tetra- are added in into reaction bulb
Hydrogen furyl bromobenzene (0.091mol), 150ml n,N-Dimethylformamide, 50ml deionized waters, 20.7g Anhydrous potassium carbonates
(1.5mol), 0.4g tetra-triphenylphosphine palladiums, be heated to 70 DEG C reaction 3 it is small when.Carry out conventional post processing, through chromatogram purification, just oneself
Alkane elutes, and ethyl alcohol recrystallization obtains white solid (compound L C-03,0.078mol) 29.2g, GC：99.5%, yield：
86.2%.
Gained white solid LC-03 is analyzed using GC-MS, the m/z of product is 372.2 (M+).
1H-NMR(300MHz,CDCl3):0.95-2.80 (m, 18H), 3.50-5.10 (m, 2H), 7.20-7.50 (m, 4H).
Embodiment 6
Technical solution according to embodiment 5, 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.
Comparative example 1
By the compound L C-01 obtained by embodiment 1 and the liquid-crystal compounds performance parameter of comparative example 1 (known compound)
Data carry out comparison arrangement, and 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
The negative dielectric anisotropic compound of structure is compared, moderate with higher negative dielectric anisotropic, rotary viscosity γ 1, good
Low temperature intersolubility and higher clearing point performance, these are exactly that improvement liquid crystal material is required, can effectively improve liquid crystal group
The dielectric anisotropy △ ε of object are closed, reduce driving voltage, the faster liquid-crystal composition of the speed that meets with a response.
Comparative example 2
By the compound 2 obtained by embodiment 3 and the liquid-crystal compounds performance parameter data of comparative example 2 (known compound)
Comparison arrangement is carried out, 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
The negative dielectric anisotropic compound of structure is compared, moderate with higher negative dielectric anisotropic, rotary viscosity γ 1, good
Low temperature intersolubility and higher clearing point performance, these are exactly that improvement liquid crystal material is required, can effectively improve liquid crystal group
The dielectric anisotropy △ ε of object are closed, reduce driving voltage, the faster liquid-crystal composition of the speed that meets with a response.
Comparative example 3
By the compound L C-03 obtained by embodiment 5 and the liquid-crystal compounds performance parameter of comparative example 3 (known compound)
Data carry out comparison arrangement, and testing result is as shown in table 3：
Table 3：The performance test results of liquid-crystal compounds
By the testing result of table 3, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
The negative dielectric anisotropic compound of structure is compared, moderate with higher negative dielectric anisotropic, rotary viscosity γ 1, good
Low temperature intersolubility and higher clearing point performance, these are exactly that improvement liquid crystal material is required, can effectively improve liquid crystal group
The dielectric anisotropy △ ε of object are closed, reduce driving voltage, the faster liquid-crystal composition of the speed that meets with a response.
In addition, discovery after herein described compound is particularly applicable in the liquid-crystal composition of conventional system, it can be with
The dielectric anisotropy △ ε of liquid-crystal composition are improved, while keep relatively low rotary viscosity γ 1 and appropriate refractive index respectively to different
Property △ n, gained liquid-crystal composition have the characteristics that significant quick response and low voltage drive feature.
Although being above described in detail with a general description of the specific embodiments to the present invention, he
Be the present invention typical example, on the basis of the present invention, it can be modified and improved, this is to those skilled in the art
For be obvious.Therefore, the present invention is not to have above description and limit, without departing from theon the basis of the spirit of the present invention
These modifications or improvements belong to the scope of protection of present invention.
Claims (22)
1. a kind of epoxypentyl class liquid-crystal compounds, it is characterised in that：With the structure as shown in general formula I：
Wherein, R represents alkyl or alkoxy with 1-12 carbon atom；Ring A represent 1,4- phenylenes, 1,4- cyclohexylidenes or
The 1,4- phenylenes that 1-4 hydrogen atom is replaced by fluorine atoms；Ring B represents 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- Asias hexamethylene
The 1,4- phenylenes that alkenyl or 1-4 hydrogen atom are each independently replaced by fluorine atoms；
M is 0,1 or 2.
2. liquid-crystal compounds according to claim 1, it is characterised in that：In structure shown in the general formula I, R expressions have
The alkyl or alkoxy of 1-5 carbon atom, ring A represent Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom by fluorine atom
Substituted 1,4- phenylenes；Ring B represents 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- cyclohexadienylidenes or 1-4 hydrogen atom quilt
The 1,4- phenylenes of fluorine atom substitution；
M is 0,1 or 2.
3. liquid-crystal compounds according to claim 2, it is characterised in that：In structure shown in the general formula I, R expressions have
The alkyl or alkoxy of 1-5 carbon atom, ring A represent Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom by fluorine atom
Substituted 1,4- phenylenes；And/or ring B represents Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-cyclohexadienylidene or 1-2 hydrogen
The 1,4- phenylenes that atom is replaced by fluorine atoms；M is 0,1 or 2.
4. liquid-crystal compounds according to claim 1, it is characterised in that：Structure shown in the general formula I is selected from following chemical combination
Object：
In above-claimed cpd I-1~I-25, R represents alkyl or alkoxy with 1-5 carbon atom.
5. liquid-crystal compounds according to claim 4, it is characterised in that：Compound
In I-1~I-25, R represents the alkyl with 2-4 carbon atom.
6. liquid-crystal compounds according to claim 1, it is characterised in that：The general formula structure is selected from following compound：
7. the preparation method of any one of the claim 1-6 liquid-crystal compounds, it is characterised in that：When ring B is 1,4- phenylenes
Or 1-4 hydrogen atom be replaced by fluorine atoms Isosorbide-5-Nitrae-phenylene when, synthetic route is as follows：
Specifically include following steps：
(1)It reacts with organolithium reagent, then is reacted with borate, obtained
(2) withWithFor raw material, pass through
Suzuki reacts, and obtains
Wherein, R, m, ring A generations in any one of R, m in compound involved by each step, ring A and claim 1-4 general formula I
The group of table is corresponding.
8. preparation method according to claim 7, it is characterised in that：In the step 1),
The molar ratio of organolithium reagent and borate is 1: 1.0~4.0: 1.0~4.0, reaction temperature -50~-100 DEG C；
And/or in the step 2),With
Molar ratio for 1: 0.9~1.2,60~120 DEG C of reaction temperature.
9. preparation method according to claim 8, it is characterised in that：The organolithium reagent is selected from s-butyl lithium, tertiary fourth
Base lithium or one or more of n-BuLi and potassium tert-butoxide, the borate be selected from trimethylborate, triisopropyl borate ester,
One or more of three isobutyl ester of butyl borate or boric acid.
10. the preparation method of any one of the claim 1-6 liquid-crystal compounds, it is characterised in that：When ring B is 1,4- Asias hexamethylene
Base, i.e., when structure is as shown in general formula III shown in general formula I：Its synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then withReaction, obtains
(2)By with boron trifluoride ether, three
Ethylsilane is reacted, and is obtained
Wherein, R, m, ring A generations in any one of R, m in compound involved by each step, ring A and claim 1-4 general formula I
The group of table is corresponding.
11. preparation method according to claim 10, it is characterised in that：In the step 1),
Organolithium reagent withMolar ratio be 1.0~4.0：1.0~4.0:
1, reaction temperature -50~-100 DEG C；
And/or in the step 2),
Boron trifluoride ether and triethyl group silicon
The molar ratio of alkane is 1: 0.5~3.0：0.5~3.0, reaction temperature -20~-100 DEG C.
12. preparation method according to claim 11, it is characterised in that：The organolithium reagent is selected from s-butyl lithium, uncle
One or more of butyl lithium or n-BuLi.
13. the preparation method of any one of the claim 1-6 liquid-crystal compounds, it is characterised in that：When ring B is 1,4- Asias hexamethylene
Alkenyl, i.e., described liquid-crystal compounds be shown in formula IV during structure,
Its synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then withReaction, obtains
(2)It is dehydrated, obtains under acid catalysis
Wherein, R, m, ring A generations in any one of R, m in compound involved by each step, ring A and claim 1-4 general formula I
The group of table is corresponding.
14. preparation method according to claim 13, it is characterised in that：
In the step 1),Organolithium reagent,
Molar ratio be 1.0~4.0：1.0~4.0: 1, reaction temperature -50~-100 DEG C；
And/or
In the step 2),With feeding intake for acid
Molar ratio is 1: 0.1~0.2,50~120 DEG C of reaction temperature；
Wherein, the acid is selected from one or more of hydrochloric acid, sulfuric acid, formic acid, acetic acid, p-methyl benzenesulfonic acid, potassium acid sulfate.
15. preparation method according to claim 14, it is characterised in that：The organolithium reagent is selected from s-butyl lithium, uncle
One or more of butyl lithium or n-BuLi.
16. preparation method according to claim 14, it is characterised in that：The acid is p-methyl benzenesulfonic acid.
17. contain any one of claim 1-6 any one of the liquid-crystal compounds or claim 7-16 the preparation method institute
The liquid-crystal composition of liquid-crystal compounds obtained.
18. liquid-crystal composition according to claim 17, which is characterized in that the matter of the liquid-crystal compounds in the composition
It is 1~60% to measure percentage.
19. liquid-crystal composition according to claim 18, which is characterized in that the matter of the liquid-crystal compounds in the composition
It is 3~50% to measure percentage.
20. liquid-crystal composition according to claim 19, which is characterized in that the matter of the liquid-crystal compounds in the composition
It is 5~25% to measure percentage.
21. any one of the claim 1-6 liquid-crystal compounds or the liquid-crystal composition any one of claim 18-20
Application in liquid crystal display device.
22. application according to claim 21, which is characterized in that the liquid crystal display device for TN, ADS, VA,
PSVA, FFS or IPS liquid crystal display.
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| CN102992972A (en) * | 2012-11-27 | 2013-03-27 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound and preparation and application thereof |
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| US20150361344A1 (en) * | 2014-06-13 | 2015-12-17 | Jnc Corporation | Dihydropyran compound, liquid crystal composition and liquid crystal display device |
| US20160230094A1 (en) * | 2015-02-06 | 2016-08-11 | Jnc Corporation | Liquid crystal compound having a 3,6-dihydro-2h-pyran ring, negative dielectric anisotropy, liquid crystal composition and liquid crystal display device |
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| CN102888227A (en) * | 2012-09-20 | 2013-01-23 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound and preparation method and application thereof |
| CN102992972A (en) * | 2012-11-27 | 2013-03-27 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound and preparation and application thereof |
| US20150361344A1 (en) * | 2014-06-13 | 2015-12-17 | Jnc Corporation | Dihydropyran compound, liquid crystal composition and liquid crystal display device |
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