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 PDF

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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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ring
carbon number
alkoxy
liquid crystal
straight chained
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莫玲超
安忠维
李建
李娟利
胡明刚
杨晓哲
杨志
车昭毅
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Xian Modern Chemistry Research Institute
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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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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

A kind of negative liquid crystal compound with benzofuran ring and combinations thereof
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.
CN201711288940.5A 2017-12-07 2017-12-07 A kind of negative liquid crystal compound with benzofuran ring and combinations thereof Pending CN107903915A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19900517A1 (en) * 1998-01-19 1999-07-22 Merck Patent Gmbh Difluorobenzofuran and dihydrodifluorobenzofuran derivatives of linear (poly)cyclic compounds
DE19909761A1 (en) * 1998-04-17 1999-10-21 Merck Patent Gmbh New optically inactive benzo(b)furan, benzo(1,2-b:4,5-b')difuran and benzo(1,2-b:5,4-b')difuran derivatives, used in liquid crystal media
WO2001021606A1 (en) * 1999-09-21 2001-03-29 Qinetiq Limited Liquid crystal compounds
CN1506358A (en) * 2002-12-06 2004-06-23 石家庄实力克液晶材料有限公司 Benzofuran derivative and its prepn and use
DE102005045849A1 (en) * 2004-10-07 2006-04-20 Merck Patent Gmbh Preparation of benzocondensed oxyheterocycle, useful in liquid crystalline mixtures, comprises regioselective opening of e.g. oxetane by metallized fluoroaromates and cyclizing the obtained propanol derivative by non-nucleophilic base
CN1867647A (en) * 2003-10-17 2006-11-22 默克专利股份有限公司 Liquid crystal medium containing fluorinated indane compounds
CN103058968A (en) * 2012-12-24 2013-04-24 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof
CN103102887A (en) * 2013-02-06 2013-05-15 江苏和成显示科技股份有限公司 Benzofuran derivative liquid crystal compound as well as composition and application thereof
CN103205263A (en) * 2013-03-13 2013-07-17 江苏和成显示科技股份有限公司 Liquid crystal composition and liquid crystal display device
CN103242856A (en) * 2013-04-11 2013-08-14 江苏和成显示科技股份有限公司 Liquid crystal composition and liquid crystal display device
CN103242862A (en) * 2013-05-30 2013-08-14 江苏和成显示科技股份有限公司 Liquid crystal composition with low-temperature storage stability and liquid crystal display device
CN103897708A (en) * 2014-03-13 2014-07-02 石家庄诚志永华显示材料有限公司 Positive dielectric anisotropy liquid crystal composition
CN104293360A (en) * 2013-07-16 2015-01-21 江苏和成显示科技股份有限公司 Liquid crystal composition and application thereof
CN106675575A (en) * 2015-11-06 2017-05-17 江苏和成显示科技股份有限公司 Dielectric negative liquid crystal compound as well as preparation method and application thereof
CN108003894A (en) * 2016-11-02 2018-05-08 达兴材料股份有限公司 Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19900517A1 (en) * 1998-01-19 1999-07-22 Merck Patent Gmbh Difluorobenzofuran and dihydrodifluorobenzofuran derivatives of linear (poly)cyclic compounds
DE19909761A1 (en) * 1998-04-17 1999-10-21 Merck Patent Gmbh New optically inactive benzo(b)furan, benzo(1,2-b:4,5-b')difuran and benzo(1,2-b:5,4-b')difuran derivatives, used in liquid crystal media
WO2001021606A1 (en) * 1999-09-21 2001-03-29 Qinetiq Limited Liquid crystal compounds
CN1506358A (en) * 2002-12-06 2004-06-23 石家庄实力克液晶材料有限公司 Benzofuran derivative and its prepn and use
CN1867647A (en) * 2003-10-17 2006-11-22 默克专利股份有限公司 Liquid crystal medium containing fluorinated indane compounds
DE102005045849A1 (en) * 2004-10-07 2006-04-20 Merck Patent Gmbh Preparation of benzocondensed oxyheterocycle, useful in liquid crystalline mixtures, comprises regioselective opening of e.g. oxetane by metallized fluoroaromates and cyclizing the obtained propanol derivative by non-nucleophilic base
CN103058968A (en) * 2012-12-24 2013-04-24 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof
CN103102887A (en) * 2013-02-06 2013-05-15 江苏和成显示科技股份有限公司 Benzofuran derivative liquid crystal compound as well as composition and application thereof
CN103205263A (en) * 2013-03-13 2013-07-17 江苏和成显示科技股份有限公司 Liquid crystal composition and liquid crystal display device
CN103242856A (en) * 2013-04-11 2013-08-14 江苏和成显示科技股份有限公司 Liquid crystal composition and liquid crystal display device
CN103242862A (en) * 2013-05-30 2013-08-14 江苏和成显示科技股份有限公司 Liquid crystal composition with low-temperature storage stability and liquid crystal display device
CN104293360A (en) * 2013-07-16 2015-01-21 江苏和成显示科技股份有限公司 Liquid crystal composition and application thereof
CN103897708A (en) * 2014-03-13 2014-07-02 石家庄诚志永华显示材料有限公司 Positive dielectric anisotropy liquid crystal composition
CN106675575A (en) * 2015-11-06 2017-05-17 江苏和成显示科技股份有限公司 Dielectric negative liquid crystal compound as well as preparation method and application thereof
CN108003894A (en) * 2016-11-02 2018-05-08 达兴材料股份有限公司 Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
G BAZIZARD-MOUYSSET: "Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 *
YUN ZHANG,SHUN-CHAO YIN,JIAN-MEI LU: "N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed allyl-aryl coupling of allylic alcohols with arylboronic acids in neat water", 《TETRAHEDRON》 *
张芳苗等: "苯并呋喃类液晶的合成", 《液晶与显示》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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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