CN107903915A - A kind of negative liquid crystal compound with benzofuran ring and combinations thereof - Google Patents
A kind of negative liquid crystal compound with benzofuran ring and combinations thereof Download PDFInfo
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- CN107903915A CN107903915A CN201711288940.5A CN201711288940A CN107903915A CN 107903915 A CN107903915 A CN 107903915A CN 201711288940 A CN201711288940 A CN 201711288940A CN 107903915 A CN107903915 A CN 107903915A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 29
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- -1 Z is singly-bound Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- KSPLOOKXNGXEKI-UHFFFAOYSA-N but-1-ynylcyclohexane Chemical class CCC#CC1CCCCC1 KSPLOOKXNGXEKI-UHFFFAOYSA-N 0.000 description 5
- 150000001907 coumarones Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 0 CCc1c2OCC(c(cc3)ccc3I)=Cc2ccc1* Chemical compound CCc1c2OCC(c(cc3)ccc3I)=Cc2ccc1* 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000013213 extrapolation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000036314 physical performance Effects 0.000 description 3
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical class FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000007445 Chromatographic isolation Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LQBMPJSTUHWGDE-UHFFFAOYSA-N 1-bromo-3-ethoxybenzene Chemical class CCOC1=CC=CC(Br)=C1 LQBMPJSTUHWGDE-UHFFFAOYSA-N 0.000 description 1
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical class FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
- PKIYFPSPIFCDDB-UHFFFAOYSA-N 4-ethoxy-2,3-difluorophenol Chemical class CCOC1=CC=C(O)C(F)=C1F PKIYFPSPIFCDDB-UHFFFAOYSA-N 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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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
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- 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
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention discloses a kind of negative liquid crystal compound with benzofuran ring, its general structure is such as shown in (1)：Wherein R1For the straight chained alkyl, alkenyl, alkoxy of carbon number 1~9；Ring A, ring B are phenyl ring, trans cyclohexane, and hydrogen atom can be substituted by one or more fluorine atoms on phenyl ring；N=0,1,2；L1、L2For halogen, hydrogen, the straight chained alkyl of carbon number 1~9, alkoxy, alkenyloxy group, and work as L2For halogen when, L1It is not straight chained alkyl；And the composition containing the compound.The liquid-crystal compounds of the present invention, has the characteristics of big negative dielectric anisotropic, high birefringence rate, suitable for the liquid crystal display modes such as VA, IPS.
Description
Technical field
The invention belongs to liquid crystal material technical field, and in particular to a kind of negative liquid crystal compound with benzofuran ring
And combinations thereof, it is mainly used for liquid crystal display.
Background technology
Liquid crystal display has the advantages that panelized, low in energy consumption, light-weight, radiationless, develops in field of information display fast
Speed.Liquid crystal display realizes display function using the optical anisotropy of liquid crystal material and the characteristic of dielectric anisotropy.Press
Classify according to display pattern, there is twisted-nematic formula (TN), super twisted nematic formula (STN), dynamic scattering mode (DSP), film crystal
Pipe drive pattern (TFT) etc..TFT liquid crystal displays can realize full color, high-resolution, wide viewing angle, quick response etc.,
To extensive use.
Liquid crystal material used in liquid crystal display in use environment temperature range, be usually -20 DEG C~+70 DEG C have to
Row phase；Must have at the same time chemical stability with height, relatively low viscosity, and the birefringence of suitable purposes, dielectric respectively to
The physics of liquid crystals property such as the opposite sex, resistivity.It is that can not meet whole use conditions with a kind of liquid-crystal compounds, it is necessary to mix ten
Remaining kind of liquid-crystal compounds forms mixed liquid crystal.Used to realize in wider temperature range.
Vertical orientated thin film transistor (TFT) driving (VA-TFT) pattern due to the angle of visibility with ultra-wide, fast response speed and
The advantages that high front contrast, become one of current mainstream LCD technology, should especially in large-screen liquid crystal display television
It is especially prominent with seeming.Compared with traditional display pattern, VA-TFT patterns its using vertical orientated technology, it is desirable to liquid crystal
Material has negative dielectric anisotropy.In addition, for LCD technology, driving voltage, lifting response speed are reduced
It is the trend of current technology development.Research shows that increase dielectric anisotropy advantageously reduces driving voltage；Improve birefringence
It is thick to advantageously reduce the box of liquid crystal display device, shortens the response time.Therefore, research is with big negative dielectric anisotropic, height
The negative liquid crystal material of birefringence, is of great significance to improving liquid crystal display device performance tool.
There are 10 pi-electrons, conjugation degree is high, is conducive to be lifted the birefringence of liquid crystal material in benzofuran ring.Patent
CN1506358A, CN103058968A, CN103102887A, DE102004053279A1 disclose the liquid with benzofuran ring
Crystalline substance, such liquid crystal are mainly positive dielectric anisotropy liquid crystal material.Benzofuran ring liquid is disclosed in patent DE19909761A1
The structure of brilliant material, it mainly has certain polar group in the 5 of benzofuran, 6 introducings, such liquid crystal is mainly rendered as
Positive dielectric anisotropy liquid crystal material.Patent CN106675575A, which is disclosed, reports the negative dielectric based on benzofuran ring respectively to different
The liquid crystal material of property, its structure such as formula 1：
But related data is not provided, only to giving correlated performance with following formula 2.
Its physical property is as follows：Δ n=-0.0287；Δ ε=- 4.72.Show small birefringence and medium negative Jie
Electrical anisotropy value.
The content of the invention
In order to overcome defect present in background technology or deficiency, further improve response speed and the driving of liquid crystal display
Voltage, the present invention provide a kind of negative liquid crystal compound based on benzofuran ring.
In order to realize above-mentioned task, the present invention takes following technical solution：
A kind of liquid-crystal compounds with benzofuran ring, its general structure is such as shown in (1)：
Wherein R1For the straight chained alkyl, alkenyl, alkoxy of carbon number 1~9；Ring A, ring B are phenyl ring, trans cyclohexane, and benzene
Hydrogen atom can be substituted by one or more fluorine atoms on ring；N=0,1,2；L1、L2For halogen, hydrogen, carbon number 1~9 straight chain alkane
Base, alkoxy, alkenyloxy group, and work as L2For halogen when, L1It is not straight chained alkyl；And the composition containing the compound.
The liquid-crystal compounds of the present invention, generates unexpected effect：Negative dielectric anisotropic significantly rises, birefringence
Rate is high, in addition, such liquid-crystal compounds has the advantages that higher light heat stability, low temperature compatibility are good, is adapted in VA-TFT
Applied in liquid crystal display.
, according to the invention it is preferred to molecular structure is as shown in 1-1~1-10：
Wherein R1Straight chained alkyl, alkoxy for carbon number 1~9, R2For the straight chained alkyl of carbon number 1~9, alkoxy, alkene oxygen
Base, R3Unbranched alkoxy, alkenyloxy group for carbon number 1~9, n=0~4.
Wherein 1-1 is further preferably from following compound：
Wherein 1-2 is further preferably from following compound：
Wherein 1-3 is further preferably from following compound：
Wherein R1Straight chained alkyl, alkoxy for carbon number 1~9, R3Unbranched alkoxy, alkenyloxy group for carbon number 1~9.
Wherein 1-4 is further preferably from following compound：
Wherein R1、R2Straight chained alkyl, alkoxy for carbon number 1~9.
Wherein 1-5 is further preferably from following compound：
Wherein R1、R2Straight chained alkyl, alkoxy for carbon number 1~9.
Wherein 1-6 is further preferably from following compound：
Wherein R1Straight chained alkyl, alkoxy for carbon number 1~9, R3Unbranched alkoxy, alkenyloxy group for carbon number 1~9.
Wherein 1-7 is further preferably from following compound：
Wherein R1、R2Straight chained alkyl, alkoxy for carbon number 1~9.
Wherein 1-8 is further preferably from following compound：
Wherein R1Straight chained alkyl, alkoxy for carbon number 1~9, R3Unbranched alkoxy, alkenyloxy group for carbon number 1~9.
Embodiment
The present invention is described in further details below in conjunction with specific embodiment.
Technical solution according to the invention, a kind of negative liquid crystal compound with benzofuran ring, general structure such as (1)
It is shown：
Wherein R1For the straight chained alkyl, alkenyl, alkoxy of carbon number 1~9；Ring A, ring B are phenyl ring, trans cyclohexane, and benzene
Hydrogen atom can be substituted by one or more fluorine atoms on ring；N=0,1,2；L1、L2For halogen, hydrogen, carbon number 1~9 straight chain alkane
Base, alkoxy, alkenyloxy group, and work as L2For halogen when, L1It is not straight chained alkyl；And the composition containing the compound.
The above-mentioned negative liquid crystal compound with benzofuran ring, is prepared using following synthetic route：
Synthetic route one：
Synthetic route two：
Specifically prepare according to the following steps：
(1) 2- fluorobenzene amphyl and iodo reagent, such as NIS, acid iodide system carry out substitution reaction, it is fluoro- to obtain 2-
6- iodobenzene amphyls；
(2) 3- bromofluorobenzenes derivative carries out aryl boric acid using lithium diisopropylamine, then is obtained by hydrogen peroxide oxidation
To the fluoro- 6- bromobenzenes amphyls of 2-；
(3) the fluoro- 6- halobenzenes amphyls of 2- and aryl ethane, in palladium catalyst, such as tetrakis triphenylphosphine palladium, two (triphens
Base phosphine) palladium bichloride, palladium, carries out Sonogashira coupling reactions and obtains target product.
It is above-mentioned containing fluorinated liquid crystal compound and aryl ethane be commercial product, purchased from the color brilliant Optoelectronics Technology stock in Xi'an
Part Co., Ltd.
Below in conjunction with specific embodiment, the present invention is described in further detail.
Test method：
The present invention relates to physical property and photoelectric properties detailed test method it is as follows：
(1) liquid-crystal phase-transition temperature and clearing point：
Using differential scanning calorimetry：Under nitrogen atmosphere, setting heating rate is 5 DEG C/min.
(2) birefringence (Δ n)：Using abbe's refractometer, under 25 DEG C of constant temperatures, ordinary light (n is measured respectivelyo) and it is non-
Ordinary light (ne) refractive index, birefringence Δ n=ne-no。
(3) dielectric constant (Δ ε)：Under 25 DEG C of constant temperatures, tested using LCR tables.Δ ε=ε∥-ε⊥, i.e. molecular long axis side
To dielectric constant (ε∥) and molecular short-axis direction dielectric constant (ε⊥) difference.
The performance test of monomer liquid crystal, is dissolved into basic components (Host) and is tested.The performance parameter of monomer,
As clearing point (Cp), Δ n, Δ ε are obtained by extrapolation.Basic components (Host) are formulated by following liquid-crystal compounds.
Code name and explanation：
Wherein liquid-crystal phase-transition temperature：Cr represents fusing point, and N represents nematic phase, and I represents liquid.
Embodiment 1：
The preparation of the fluoro- 5- ethyoxyls benzofurans of 2- (4- propyl group) cyclohexyl -6,7- two：
Concrete structure formula is as follows：
Preparation process is as follows：
(1) bis- fluoro- 4- hydroxy phenetoles of 17.4g (0.1mol) 2,3-, 100ml chloroforms are sequentially added into 250ml there-necked flasks
In, 24.8g (0.11mol) N- N-iodosuccinimides (NIS) are added portionwise at room temperature, after 2h is reacted in stirring, stop reaction.Add
Water extracts, and after washing is extracted three times with chloroform, merges organic phase.Anhydrous magnesium sulfate is dried, and filtering is spin-dried for obtaining brown liquid
21.5g, yield 73%.
(2) under nitrogen protection, by 8.3g (55mmol) 4- cyclohexyl ethyl-acetylenes, bis- fluoro- 4- of 15.0g (50mmol) 2,3-
Hydroxyl -5- iodobenzenes ether, 0.655g (2.5mmol) triphenylphosphine, 0.478g (2.5mmol) iodate Asia ketone, 1.05g
(1.5mmol) two (triphenylphosphine) palladium bichloride, 100mL triethylamines add reaction bulb.60 DEG C are warming up to after 40 DEG C of reaction 1h of heating
Continue stirring reaction 8h.After stopping reaction, room temperature is cooled to, filtering is spin-dried for, and normal heptane is eluant, eluent, column chromatographic isolation and purification,
Obtain white powder 7.4g, yield 46%.
Structural Identification data are as follows：
1H NMR (δ, CDCl3):0.881-0.910 (t, J=7Hz, 3H), 0.985-1.068 (m, 2H), 1.181-1.226
(m,2H),1.236-1.375(m,3H),1.398-1.481(m,5H),1.845-1.878(m,2H),2.112-2.139(m,
2H),2.626-2.687(m,1H),4.066-4.108(m,2H),6.243-6.248(d,1H),6.754-6.771(m,1H)
MS (70eV) m/z (%)：322(100),237(47),135(33).
The compound gone out synthesized by above Structural Identification as shown by data is strictly 2- (4- propyl group) cyclohexyl -6,7- two fluoro-
5- ethyoxyl benzofurans.
DSC tests its liquid-crystal phase-transition temperature, as a result for：Cr 77.8I.
It is dissolved in basic components according to 15% mass ratio and carries out quantitative measurement, extrapolation obtains performance parameter
For：Δ n=0.0920；Δ ε=- 6.34.
Compared with patent CN106675575A discloses 1 structure of formula of report, its negative dielectric anisotropic value has larger
Improve, add 34%.
Embodiment 2：
The preparation of the fluoro- 5- ethyoxyls benzofurans of 2- (4- propyl group) phenyl -6,7- two：
Concrete structure formula is as follows：
Preparation process is as follows：
Using the 4- cyclohexyl ethyl-acetylenes in 4- propyl group phenylacetylenes alternate embodiment 1, same method synthesizes 2- (4-
Propyl group) the fluoro- 5- ethyoxyls benzofurans of phenyl -6,7- two.
Structural Identification data are as follows：
1H NMR (δ, CDCl3):0.930-0.959 (t, J=7Hz, 3H), 1.425-1.453 (t, J=7Hz, 3H),
1.606-1.681 (m, 2H), 2.572-2.603 (t, J=7.5Hz, 2H), 4.037-4.078 (m, 2H), 6.745-6.773 (m,
2H),7.188-7.214(d,2H),7.657-7.673(d,2H)。
MS (70eV) m/z (%)：259(100),316(84),287(48).
DSC tests its liquid-crystal phase-transition temperature, as a result for：Cr 63.6(N34.5)I.
It is dissolved in basic components according to 15% mass ratio and carries out quantitative measurement, extrapolation obtains performance parameter
For：Δ n=0.2313；Δ ε=- 5.54.
Embodiment 3：
The preparation of 2- (4- propyl group) cyclohexyl -6- ethyoxyl -7- Fluorobenzofurs, concrete structure formula are as follows：
(1) under nitrogen protection, the bromo- 2- fluorobenzene ether of 21.9g (0.1mol) 4-, the 300mL tetrahydrofuran dried are added
Reaction bulb, system are cooled to -78 DEG C, and 50mL (0.12mol) lithium diisopropylamine is added dropwise, and about 40min is added dropwise, and keep the temperature
1h, is added dropwise the tetrahydrofuran solution dissolved with 22.6g (0.12mol) triisopropyl borate ester, after being added dropwise, rises again naturally to room
Temperature.It is in acidity to add hydrochloric acid to reaction system, adds normal heptane extractive reaction liquid, and water is mutually extracted three times with normal heptane, merges organic phase,
Anhydrous magnesium sulfate is dried, and filtering obtains light yellow solid after being spin-dried for, white solid 12.8g, yield 49% are obtained after normal heptane recrystallization.
(2) under nitrogen protection, by the bromo- 3- ethoxybenzenes boric acid of the fluoro- 6- of 7.9g (30mmol) 2-, 100mL tetrahydrofurans add
Enter reaction bulb, system is cooled to 5 DEG C, and 5.1g (45mmol) hydrogen peroxide solution is added dropwise, and after being added dropwise, continues stirring reaction 2h.
Toluene extraction is added in system three times, merges organic phase, anhydrous magnesium sulfate drying, filtering is spin-dried for, and is obtained light yellow liquid 5.4g, is received
Rate 77%.
(3) under nitrogen protection, by 3.6g (24mmol) 4- cyclohexyl ethyl-acetylenes, the fluoro- 3- hydroxyls of 4.7g (20mmol) 2--
4- Bromoethyl phenyl ethers, 0.314g (1.2mmol) triphenylphosphine, 0.229g (1.2mmol) iodate Asia ketone, 0.842g (1.2mmol) two
(triphenylphosphine) palladium bichloride, 100mL triethylamines add reaction bulb.60 DEG C of stirring reaction 12h of heating.After stopping reaction, it is cooled to
Room temperature, filtering are spin-dried for, and normal heptane is eluant, eluent, and column chromatographic isolation and purification, obtains white powder 3.5g, yield 48%.
Structural Identification data are as follows：
1H NMR (δ, CDCl3):0.866-0.896 (t, J=7.5Hz, 3H), 0.988-1.071 (m, 2H), 1.182-
1.228(m,2H),1.248-1.378(m,3H),1.408-1.491(m,5H),1.844-1.878(m,2H),2.130-2.164
(m,2H),2.638-2.700(m,1H),4.114-4.156(m,2H),6.253-6.261(m,1H),6.842-6.873(m,
1H),7.065-7.084(d,1H)。
MS (70eV) m/z (%)：304(100),191(35),219(30),178(20).
Embodiment 4
The preparation of 2- (4- propyl group) phenyl -6- ethyoxyl -7- Fluorobenzofurs, concrete structure formula are as follows：
Preparation process is as follows：
Using the 4- cyclohexyl ethyl-acetylenes in 4- propyl group phenylacetylenes alternate embodiment 3, same method synthesizes 2- (4-
Propyl group) phenyl -6- ethyoxyl -7- Fluorobenzofurs.
Structural Identification data are as follows：
1H NMR (δ, CDCl3):0.935-0.964 (t, J=7Hz, 3H), 1.431-1.459 (t, J=7Hz, 3H),
1.619-1.693 (m, 2H), 2.589-2.619 (t, J=7Hz, 2H), 4.134-4.176 (m, 2H), 6.861-6.907 (m,
2H),7.142-7.162(m,1H),7.217-7.233(t,2H),7.727-7.743(m,2H)。
MS (70eV) m/z (%)：269(100),298(82),241(67),183(12).
Embodiment 5
The preparation of 2- (4- (4- butyl) cyclohexyl) fluoro- 5- ethyoxyls benzofuran of phenyl -6,7- bis-, concrete structure formula is such as
Under：
Using the 4- cyclohexyl ethyl-acetylenes in 4- (4- butyl) cyclohexyl benzene acetylene alternate embodiment 1, same method
Synthesize 2- (4- (4- butyl) cyclohexyl) fluoro- 5- ethyoxyls benzofurans of phenyl -6,7- two.
Structural Identification data are as follows：
1H NMR (δ, CDCl3):0.891-0.915 (t, J=7Hz, 3H), 0.978-1.075 (m, 2H), 1.211-1.345
(m,8H),1.363-1.475(m,5H),1.822-1.894(m,4H),4.054-4.095(m,2H),6.769-6.794(m,
2H),7.214-7.237(d,2H),7.678-7.694(d,2H)。
MS (70eV) m/z (%)：412(100),272(12),287(8).
Formulation Example 1
It is as shown in the table to be formulated 1 component.
Physical performance data is as follows：
Fusing point<-20℃；Clearing point：85℃；
Δ n (589nm, 25 DEG C)=0.1011；
Δ ε=- 3.5.
Formulation Example 2
It is as shown in the table to be formulated 2 components.
Physical performance data is as follows：
Fusing point<-20℃；Clearing point：81℃；
Δ n (589nm, 25 DEG C)=0.0987；
Δ ε=- 3.8.
Formulation Example 3
It is as shown in the table to be formulated 3 components.
Physical performance data is as follows：
Fusing point<-20℃；Clearing point：84℃；
Δ n (589nm, 25 DEG C)=0.1008；
Δ ε=- 3.9.
Claims (7)
1. a kind of negative liquid crystal compound with benzofuran ring, it is characterised in that general structure is such as shown in (1)：
Wherein R1For the straight chained alkyl, alkenyl or alkoxy of carbon number 1~9；Ring A, ring B are respectively phenyl ring or trans cyclohexane, and benzene
Hydrogen atom can be substituted by one or more fluorine atoms on ring；N=0~2；L1、L2Respectively halogen, hydrogen, carbon number 1~9 it is straight
Alkyl group, alkoxy or alkenyloxy group, and work as L2For halogen when, L1It is not straight chained alkyl.
2. negative liquid crystal compound as claimed in claim 1, it is characterised in that the n=0, ring B for trans cyclohexane or
Phenyl ring, and hydrogen atom can be substituted by one or more fluorine atoms on phenyl ring；R1For the straight chained alkyl or alcoxyl of carbon number 2~7
Base, L1For hydrogen or the unbranched alkoxy or alkenyloxy group of carbon number 1~5；L2For the straight chained alkyl, alkoxy, alkenyloxy group of carbon number 1~5,
Or halogen.
3. negative liquid crystal compound as claimed in claim 1, it is characterised in that the n=1, ring A are trans cyclohexane,
Ring B is phenyl ring, and hydrogen atom can be substituted by one or more fluorine atoms on phenyl ring, R1Straight chained alkyl, alkane for carbon number 2~7
Epoxide, L1Unbranched alkoxy, alkenyloxy group for carbon number 1~5, L2For halogen.
4. negative liquid crystal compound as claimed in claim 1, it is characterised in that the n=1, ring A, ring B are trans ring
Hexane, R1Straight chained alkyl, alkoxy for carbon number 2~7, L1For hydrogen, L2For the straight chained alkyl of carbon number 1~5, alkoxy, alkene oxygen
Base.
5. negative liquid crystal compound as claimed in claim 1, it is characterised in that the n=1, ring A, ring B are phenyl ring,
And hydrogen atom can be substituted by one or more fluorine atoms on phenyl ring, R1Straight chained alkyl, alkoxy for carbon number 2~7, L1For carbon
The unbranched alkoxy of number 1~5, alkenyloxy group, L2For halogen.
6. the composition of the liquid-crystal compounds comprising general formula (1) as described in claim 1-5, it is characterized in that the liquid of general formula (1)
Crystallization compound mass content is 0.1%~40%.
7. liquid-crystal composition as claimed in claim 6, it is characterised in that further include following liquid-crystal compounds, its structural formula is such as
Formula (2)：
Wherein, R1、R2For straight chained alkyl, alkoxy, alkenyl or alkenyloxy group, ring A, ring B, ring C are respectively phenyl ring or trans cvclohexvl
Alkane, and hydrogen atom can be substituted by one or more fluorine atoms on phenyl ring, Z is singly-bound, acetenyl ,-CH2-O-、-CF2- O- or-
CH2-CH2-, m is 0~2.
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| CN109762577A (en) * | 2019-02-12 | 2019-05-17 | 西安近代化学研究所 | A kind of liquid-crystal compounds, composition and compounds process for production thereof based on pentamethylene and benzofuran skeleton |
| CN113512427A (en) * | 2021-08-17 | 2021-10-19 | 烟台显华化工科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device |
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| CN109762577B (en) * | 2019-02-12 | 2021-11-23 | 西安近代化学研究所 | Liquid crystal compound based on cyclopentanobenzofuran framework, composition and preparation method of compound |
| CN113512427A (en) * | 2021-08-17 | 2021-10-19 | 烟台显华化工科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device |
| CN113512427B (en) * | 2021-08-17 | 2023-04-28 | 烟台显华科技集团股份有限公司 | Liquid crystal compound having negative dielectric anisotropy, liquid crystal composition, and liquid crystal display device |
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