CN108018049B - Replace the liquid-crystal compounds of benzo furan nucleus with 5,6- difluoro - Google Patents

Replace the liquid-crystal compounds of benzo furan nucleus with 5,6- difluoro Download PDF

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CN108018049B
CN108018049B CN201610964519.0A CN201610964519A CN108018049B CN 108018049 B CN108018049 B CN 108018049B CN 201610964519 A CN201610964519 A CN 201610964519A CN 108018049 B CN108018049 B CN 108018049B
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CN108018049A (en
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安忠维
李建
车昭毅
莫玲超
李娟利
胡明刚
杨晓哲
杨志
宋宽广
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Xian Modern Chemistry Research Institute
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    • 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

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Abstract

The invention discloses a kind of liquid-crystal compounds that there is 5,6- difluoro to replace benzo furan nucleus, it is characterised in that general structure is such as shown in (1):Wherein, R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；Ring A is phenyl ring, trans-cyclohexane, and hydrogen atom can be replaced one or more fluorine atoms on phenyl ring；N=0,1,2；X1、X2、X3For hydrogen atom or fluorine atom.The present invention has the characteristics that big dielectric anisotropy, high birefringence rate, lower rotary viscosity, mesophase range are wider, is suitable for the liquid crystal display modes such as TFT liquid crystal display, especially IPS, TN, OCB, Lcos, PDLC, blue phase.

Description

Replace the liquid-crystal compounds of benzo furan nucleus with 5,6- difluoro
Technical field
The invention belongs to liquid crystal material technical fields, and in particular to a kind of LCD compound with fluoro benzo furan nucleus Object is mainly used for liquid crystal display.
Background technique
Liquid crystal display has many advantages, such as 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.It presses Classify according to display pattern, there is twisted-nematic formula (TN), super twisted nematic formula (STN), dynamic scattering mode (DSP), film crystal Pipe drive mode (TFT) etc..Full color, high-resolution, wide viewing angle, quick response etc. may be implemented in TFT liquid crystal display, has obtained It is most important display technology currently on the market to extensive use.
Liquid crystal material used in liquid crystal display in use environment temperature range, usually -20 DEG C~+70 DEG C have to Column phase；Must have chemical stability with height simultaneously, the birefringence of lower viscosity and suitable purposes, dielectric respectively to The physics of liquid crystals property such as the opposite sex, resistivity.It is to be unable to satisfy whole use conditions with a kind of liquid-crystal compounds, it is necessary to will be several Kind, even ten several above liquid-crystal compounds carry out compounding and form mixed liquid crystal material, can meet actually making for display device With requiring.
TFT LCD technology requires used liquid crystal material that must have high resistivity, high voltage holding ratio and light Thermal stability.By introducing liquid-crystal compounds of the fluorine atom as polar group, the groups such as more traditional cyano-containing in the molecule Liquid-crystal compounds, resistivity, voltage retention, stability greatly improves, can satisfy the demand of TFT display technology, It is widely applied in TFT liquid crystal display.For LCD technology, reducing driving voltage, promoting response speed is to work as The trend of preceding technology development.The study found that increasing dielectric anisotropy advantageously reduces driving voltage；It is advantageous to improve birefringence The thickness between the box for reducing liquid crystal display device shortens the response time；Using the liquid crystal material of low rotary viscosity, can substantially contract The short liquid crystal response time.
Therefore, there is an urgent need to research and develop to be provided simultaneously with big dielectric anisotropy, high birefringence rate and low rotary viscosity, steady Qualitative good liquid crystal material.However in the liquid crystal material applied at present, dielectric anisotropy is big and birefringence is high liquid-crystalization Object is closed, rotary viscosity is often also higher, and which has limited the further promotions of liquid crystal display response speed.
There are 10 pi-electrons, conjugation degree is high, is conducive to the birefringence for promoting liquid crystal material in benzofuran ring. J.Mater.Chem., 2001,11,2759-2772. report benzofuran liquid crystal material and its liquid crystalline phase row containing cyano For.However the compound resistivity containing cyano is lower, is not suitable for applying in TFT liquid crystal display.
The liquid crystal with benzofuran ring is disclosed in patent CN1506358A.Benzofuran replaces position master in such liquid crystal To be 2,5-, and have no polar substituent on benzofuran ring, the dielectric anisotropy of such liquid crystal molecule is still not big enough.
Disclosing in patent CN 103058968A and CN 103102887A has-CF2The benzofuran ring liquid of O- bridged bond Brilliant material, benzofuran replaces position to be mainly 2,5- in such liquid crystal, and has no polar substituent on benzofuran ring.
The structure of benzofuran ring liquid crystal material, but disclosed liquid crystal molecule liquid are disclosed in patent DE19909761A1 Crystal phase area is relatively narrow, and dielectric anisotropy is smaller.
Disclosed in patent DE102004053279A1 5,6,7- trifluoros replace benzo furan nucleus liquid crystal material, however this The dielectric anisotropy of class material is big not enough.
Summary of the invention
In order to overcome defect present in background technique or deficiency, further improve the response speed and driving of liquid crystal display Voltage, the object of the present invention is to provide a kind of liquid-crystal compounds for replacing benzo furan nucleus based on 5,6- difluoro.
In order to realize that above-mentioned task, the present invention take following technical solution:
A kind of liquid-crystal compounds with benzofuran ring, it is characterised in that general structure is such as shown in (1):
Wherein, R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；Ring A is phenyl ring, trans-cyclohexane, and on phenyl ring Hydrogen atom can be replaced one or more fluorine atoms；N=0,1,2；X1、X2、X3For hydrogen atom or fluorine atom.
Liquid-crystal compounds of the invention, position and quantity by specific fluoro substituents in control benzofuran ring, that is, select Selecting property in 5,6- progress difluoro substitutions, produce unexpected effect: dielectric anisotropy is substantially increased, birefringence Height, while keeping lower rotary viscosity；And in the further fluoro of adjacent phenyl rings, the dielectric that can also further increase molecule is each Anisotropy；In addition, such novel liquid crystal compound clearing point also with higher and higher light, thermal stability, non- Often it is suitble to apply in TFT liquid crystal display.
General formula (1) compound according to the present invention, preferred molecular structure is as shown in (1) -1~9:
Wherein R is straight chained alkyl.
Wherein (1) -1 further preferably from following compound:
Wherein (1) -2 further preferably from following compound:
Wherein (1) -3 further preferably from following compound:
Wherein (1) -4 further preferably from following compound:
Wherein (1) -5 further preferably from following compound:
Wherein (1) -6 further preferably from following compound:
Wherein (1) -7 further preferably from following compound:
Wherein (1) -8 further preferably from following compound:
Wherein (1) -9 further preferably from following compound:
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Below in an example, liquid-crystal phase-transition temperature: C represents fusing point, and N represents nematic phase, and I represents liquid.
Technical solution according to the invention, the present embodiment provide a kind of liquid crystal that there is 5,6- difluoro to replace benzo furan nucleus Compound, general structure is such as shown in (1):
Wherein, R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；Ring A is phenyl ring, trans-cyclohexane, and on phenyl ring Hydrogen atom can be replaced one or more fluorine atoms；N=0,1,2；X1、X2、X3For hydrogen atom or fluorine atom.
It is above-mentioned containing fluorinated liquid crystal compound, used raw material is commercial product, be purchased from Xi'an Cai Jing photoelectricity section Skill limited liability company, synthetic route are as follows:
Specifically it is prepared according to the following steps:
(1) 5,6- difluorobenzo-fur and bromide reagent, such as NBS, bromine carry out substitution reaction, obtain intermediate 2- Bromo- 5,6- difluorobenzo-fur；
(2) bromo- 5, the 6- difluorobenzo-fur of 2- and aryl boric acid derivative, in palladium catalyst, as tetrakis triphenylphosphine palladium, Two (triphenylphosphine) palladium chlorides, palladium acetate etc. or loaded catalyst, such as the effects of palladium/carbon under, carry out Suzuki coupling reaction Obtain target product.
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 (Tni):
Polarisation thermal station method: liquid crystalline sample being coated on glass slide and is placed in cross-polarized light microscopic heating stand, setting heating speed Rate is 2 DEG C/min.The temperature of liquid crystalline sample blackening by illuminated state, as clearing point are observed in petrographic microscope.
Or use differential scanning calorimetry: under nitrogen atmosphere, setting heating rate is 3~5 DEG C/min.
(2) (Δ n): using abbe's refractometer to birefringence, under 25 DEG C of constant temperatures, measures ordinary light (n respectivelyo) and it is non- Ordinary light (ne) refractive index, birefringence Δ n=ne- no
(3) it under dielectric constant (Δ ε): 25 DEG C of constant temperatures, is tested using LCR table.Δ ε=ε∥-ε⊥, i.e. molecular long axis side To dielectric constant (ε∥) and molecular short-axis direction dielectric constant (ε⊥) difference.
(4) elastic constant (K11, K33): under 25 DEG C of constant temperatures, by testing liquid crystal capacitance-voltage (C-V) curve, intend Conjunction obtains K11And K33。
(5) rotary viscosity (γ1): under 25 DEG C of constant temperatures, by applying voltage to liquid crystal test box, test liquid crystal molecule With the transient current value Ip of electric field movement deflection, rotary viscosity γ is calculated1。
The performance test of monomer liquid crystal is dissolved into following basic components (Host) and is tested.The performance of monomer Parameter, such as clearing point, Δ ε, Δ n, γ1It is obtained by extrapolation.Basic components (Host) by following three kinds of liquid-crystal compounds according to Weight ratio 1:1:1 is formulated.
Code name and explanation:
Wherein liquid-crystal phase-transition temperature: C represents fusing point, and S represents smectic phase, and N represents nematic phase, and Iso represents liquid.
Embodiment 1:
The fluoro- 2- of 5,6- bis- (4- propyl phenyl) benzofuran
(1) in the there-necked flask with agitating device, 5,6- difluorobenzo-fur 15.4g is added to 200ml dichloromethane In alkane, 17.6g NBS is added portionwise in reaction solution at room temperature.2h is stirred at room temperature.Revolving removes solvent, crosses silica gel Column, petroleum ether elution.It is concentrated to get solid 21g.
(2) under nitrogen protection, by bromo- 5, the 6- difluorobenzo-fur of 2- obtained by upper step, 4- propyl phenyl boric acid 16.4g, four or three Phenylphosphine closes palladium 2.3g, potassium carbonate 27.6g, tetrabutylammonium bromide 16.1g, toluene 100ml, ethyl alcohol 100ml, water 100ml and is added Into there-necked flask, heating reflux reaction 8h.It is cooling, it is extracted with toluene, organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry.Have Machine layer is concentrated to dryness, and crosses silica gel column chromatography, petroleum ether elution.It is recrystallized 3 times with petroleum ether and obtains white crystal 17.6g, GC contains Amount is 99.8%.
Structural Identification data are as follows:
1H NMR(CDCl3, 500MHz) and δ: 0.96 (t, J=7.5Hz, 3H), 1.61-1.73 (m, 2H), 2.63 (t, J= 7.5Hz,2H),6.89(s,1H),7.21-7.37(m,4H),7.66-7.78(m,2H)。
MS m/z (RI, %): 272 (M+,56),243(100),214(14)。
DSC tests fusing point are as follows: C 118.18Iso.
The compound is dissolved into basic components with 5% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=14 DEG C；Δ n=0.2077；Δ ε=17.6；γ1=48.9mPas.
Embodiment 2:
The fluoro- 2- of 5,6- bis- (4- n-pentyl phenyl) benzofuran is made in method similar to Example 1.
Structural Identification data are as follows:
1H NMR(CDCl3, 500MHz) and δ: 0.90 (t, J=6.7Hz, 3H), 1.35 (t, J=8.5Hz, 4H), 1.60- 1.71 (m, 2H), 2.64 (t, J=7.7Hz, 2H), 6.88 (s, 1H), 7.19-7.38 (m, 4H), 7.71 (d, J=8.0Hz, 2H)。
MS m/z (RI, %): 300 (M+,60),243(100),214(13)。
DSC tests fusing point are as follows: C 109.47Iso
The compound is dissolved into basic components with 5% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=2 DEG C；Δ n=0.1977；Δ ε=14.9；γ1=92.9mPas.
Embodiment 3:
2- (4- n-propyl -2,6- difluorophenyl) -5,6- difluorobenzo-fur
2- (4- n-propyl -2,6- difluorophenyl) -5,6- difluorobenzo-fur is made in method similar to Example 1.
1H NMR(CDCl3, 500MHz) and δ: 0.97 (t, J=7.3Hz, 3H), 1.62-1.72 (m, 2H), 2.62 (t, J= 15.0Hz,2H),6.82-6.88(m,2H),7.07(s,1H),7.33-7.42(m,2H)。
MS m/z (RI, %): 308 (M+,65),279(100),250(12),230(7)。
DSC tests fusing point are as follows: C 71.49Iso
The compound is dissolved into basic components with 15% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=-14.6 DEG C；Δ n=0.1887；Δ ε=27.9；γ1=94.3mPas.
Embodiment 4:
2- (4- normal-butyl -2,6- difluorophenyl) -5,6- difluorobenzo-fur
2- (4- normal-butyl -2,6- difluorophenyl) -5,6- difluorobenzo-fur is made in method similar to Example 1.
Structural Identification data are as follows:
1H NMR(CDCl3, 500MHz) and δ: 0.95 (t, J=7.4Hz, 3H), 1.31-1.44 (m, 2H), 1.57-1.68 (m, 2H), 2.59-2.69 (m, 2H), 6.81-6.89 (m, 2H), 7.06 (t, J=5.2Hz, 1H), 7.32-7.42 (m, 2H).
MS m/z (RI, %): 279 (100), 322 (M+,74),250(10).
DSC tests fusing point are as follows: C 54.49Iso.
The compound is dissolved into basic components with 15% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=-16 DEG C；Δ n=0.1764；Δ ε=24.2；γ1=104.2mPas.
Embodiment 5:
2- (the fluoro- 4- xenyl of 4 '-n-pentyl -3,5- two) -5,6- difluorobenzo-fur
2- (the fluoro- 4- xenyl of 4 '-n-pentyl -3,5- bis-) -5,6- difluoro benzo is made in method similar to Example 1 Furans.
Structural Identification data are as follows:
1H NMR(CDCl3, 800MHz) δ: 0.97 (t, J=7.2Hz, 3H), 1.67 (m, 2H), 2.63 (t, J=8.0Hz, 2H),7.12(s,1H),7.23(d,2H),7.26(d,2H),7.37(m,2H),7.49(d,2H)。
MS m/z (RI, %): 384 (M+,96),355(100)。
DSC tests liquid-crystal phase-transition temperature are as follows: C97.77S 171.71N 179.10Iso.
The compound is dissolved into basic components with 5% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=138.7 DEG C；Δ n=0.3057；Δ ε=27.4；γ1=189.7mPas.
Embodiment 6:
2- (the fluoro- 4- xenyl of 4'- n-pentyl -3-) -5,6- difluorobenzo-fur
2- (the fluoro- 4- xenyl of 4'- n-pentyl -3-) -5,6- difluorobenzo-fur is made in method similar to Example 1.
Structural Identification data are as follows:
1H NMR(CDCl3, 800MHz) and δ: 0.97 (m, 3H), 1.41 (m, 4H), 1.71 (m, 2H), 2.70 (t, J= 7.2Hz,2H),7.17(s,1H),7.30(d,2H),7.35(t,2H),7.41(d,1H),7.49(d,1H),7.55(d,2H), 7.98(t,1H)。
MS m/z (RI, %): 394 (M+,92),337(100)。
DSC tests liquid-crystal phase-transition temperature are as follows: C95.03S 202.38N 207.02Iso
The compound is dissolved into basic components with 5% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=138.7 DEG C；Δ n=0.3057；Δ ε=27.4；γ1=189.7mPas.
Embodiment 7:
2- (4- (4- normal-butyl cyclohexyl) phenyl) -5,6- difluorobenzo-fur
2- (4- (4- normal-butyl cyclohexyl) phenyl) -5,6- difluorobenzo-fur is made in method similar to Example 1.
Structural Identification data are as follows:
1H NMR(CDCl3,500MHz)δ:0.89-0.92(m,3H),1.03-1.11(m,2H),1.23-1.33(m,7H), 1.43-1.54(m,2H),1.87-1.93(m,4H),2.47-2.54(m,1H),6.89(s,1H),7.28-7.34(m,4H), 7.73 (d, J=8.3Hz, 2H).
MS m/z (RI, %): 368 (M+,100),269(30),256(32),243(30)。
DSC tests liquid-crystal phase-transition temperature are as follows: C124.67S140.53N 209.38Iso.
The compound is dissolved into basic components with 5% weight ratio and carries out quantitative measurement, extrapolation obtains performance 2:Tni=179.2 DEG C of parameter；Δ n=0.2117；Δ ε=12.2；γ1=275.7mPas.
Embodiment 8:
2- (the fluoro- 4- of 2- (4- n-propyl cyclohexyl) phenyl) -5,6- difluorobenzo-fur
2- (the fluoro- 4- of 2- (4- n-propyl cyclohexyl) phenyl) -5,6- difluoro benzo is made in method similar to Example 1 Furans.
Structural Identification data are as follows:
1H NMR(CDCl3, 800MHz) and δ: 0.90 (t, J=7.2Hz, 3H), 1.03 (m, 2H), 1.20 (m, 2H), 1.29 (m,1H),1.34(m,2H),1.42(m,2H),1.88(m,4H),2.47(m,1H),7.00(d,1H),7.06(d,2H),7.29 (m,2H),7.81(t,1H)；IR(KBr)ν/cm-1:2957,2923,2848,1625,1586,1501,1482,1458,1423, 1356,1244,1226,1190,1144,1112,1020,942,858；MS m/z (RI, %): 372 (M+,100),274(34), 261(26),287(20)。
DSC tests liquid-crystal phase-transition temperature are as follows: C118.37N 191.37Iso
The compound is dissolved into basic components with 10% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=168.7 DEG C；Δ n=0.2117；Δ ε=18.2；γ1=409.7mPas.
Embodiment 9:
2- (the fluoro- 4- of 2,6- bis- (4- n-propyl cyclohexyl) phenyl) -5,6- difluorobenzo-fur
2- (2,6- bis- fluoro- 4- (4- n-propyl cyclohexyl) phenyl) -5,6- difluoro is made in method similar to Example 1 Benzofuran.
Structural Identification data are as follows:
1H NMR(CDCl3, 500MHz) and δ: 0.91 (t, J=7.5Hz, 3H), 1.01-1.09 (m, 2H), 1.20-1.24 (m, 2H), 1.25-1.46 (m, 5H), 1.87-1.93 (m, 4H), 2.46-2.52 (m, 1H), 6.87 (d, J=10.3Hz, 2H), 7.06 (s,1H),7.33-7.39(m,2H)。
MS m/z (RI, %): 390 (M+,100),292(38),279(29)。
DSC tests liquid-crystal phase-transition temperature are as follows: C 112.48N 170.17Iso.
The compound is dissolved into basic components with 10% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=145.0 DEG C；Δ n=0.2097；Δ ε=23.1；γ1=374.7mPas.
Embodiment 10:
2- (2,6- bis- fluoro- 4- (4- pentyl cyclohexyl) phenyl) -5,6- difluorobenzo-fur
2- (2,6- bis- fluoro- 4- (4- pentyl cyclohexyl) phenyl) -5,6- difluoro is made in method similar to Example 1 Benzofuran.
Structural Identification data are as follows:
1H NMR(CDCl3, 500MHz) and δ: 0.90 (t, J=7.2Hz, 3H), 1.00-1.08 (m, 2H), 1.19-1.35 (m, 9H), 1.36-1.45 (m, 2H), 1.87-1.92 (m, 4H), 2.44-2.51 (m 1H), 6.86 (d, J=10.5Hz, 2H), 7.05 (s,1H),7.32-7.38(m,2H)。
MS m/z (%): 418 (M+,100),292(39),279(36)。
DSC tests liquid-crystal phase-transition temperature are as follows: C89.56N 169.86Iso.
The compound is dissolved into basic components with 10% weight ratio and carries out quantitative measurement, extrapolation obtains performance Parameter are as follows: Tni=147.2 DEG C；Δ n=0.2077；Δ ε=21.7；γ1=387.0mPas.
Comparative example 1:
It is reported in Angew.Chem.In.Ed, 2000,39,4216-4235 and is applied and divides in TFT liquid crystal display Contain the liquid-crystal compounds of 3,4- difluorobenzene in sub- end:
The fundamental performance parameter of the compound are as follows: C55N105.4Iso, Tni=107.8 DEG C, Δ ε=6.3；Δ n= 0.144；γ1=210mPas.
2 compound of the embodiment of the present invention:
Its fundamental performance parameter are as follows: Tni=2 DEG C；Δ ε=14.9；Δ n=0.1977；γ1=92.9mPas.
Although can be seen that the compounds of this invention molecular end also only there are two polarity fluorine atom, Δ ε is but equivalent to 2.37 times of comparative example compound；And Δ n value also increases considerably；More it is surprising that γ1Also reach reduction, only phase When in the 44% of comparative example compound.
Comparative example 2:
The 5,6,7- trifluoro that benzofuran is disclosed in patent DE102004053279A1 replaces ring liquid crystal material:
Performance parameter: C90N173.9Iso, Tni=157.9 DEG C, Δ ε=13.8；Δ n=0.1231；γ1= 512mPa·s。
8 compound of the embodiment of the present invention:
Its performance parameter: C118.37N 191.37Iso, Tni=168.7 DEG C, Δ ε=18.2；Δ n=0.2117；γ1 =409.7mPas.
Although there are three polarity fluorine atoms to replace for compound in the compounds of this invention and comparative example, the compounds of this invention Compared with comparative example compound, not only clearing point is higher, but also Δ ε and Δ n are significantly promoted, rotary viscosity γ1Then substantially Degree reduces.The compounds of this invention is compared compared with compound disclosed in DE102004053279A1, comprehensively better than comparison in performance Example compound, achieves unexpected technical effect.
Comparative example 3:
Benzofuran ring liquid crystal material is disclosed in patent DE19909761A1:
Liquid-crystal phase-transition temperature disclosed in specification are as follows: C81N 121.1Iso, nematic temperature range are 40.1 DEG C.
8 compound of the embodiment of the present invention:
Its liquid-crystal phase-transition temperature range are as follows: C89.56N 169.86Iso, nematic temperature range are 80.3 DEG C.
As can be seen that the compounds of this invention clearing point is sharply increased, mesophase range is significantly increased.

Claims (4)

  1. The liquid-crystal compounds that 1. there is one kind 5,6- difluoro to replace benzo furan nucleus, it is characterised in that general structure is such as shown in (1):
    Wherein, R is the straight chained alkyl or alkoxy of carbon number 1~9；Ring A is phenyl ring or trans-cyclohexane, and hydrogen atom on phenyl ring It can be replaced one or more fluorine atoms；N=0,1 or 2；X1For H or F, X2、X3For F.
  2. 2. liquid-crystal compounds according to claim 1, it is characterised in that n=0, X1=H.
  3. 3. liquid-crystal compounds according to claim 1, it is characterised in that n=1, ring A are trans-cyclohexane, X1=H.
  4. 4. liquid-crystal compounds according to claim 1, it is characterised in that n=1, ring A are phenyl ring, X1=H.
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CN109181712B (en) * 2018-10-10 2021-08-20 西安近代化学研究所 Benzofuran liquid crystal compound with difluoromethyl ether bridge bond and composition thereof
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
CN114989120B (en) * 2022-06-14 2024-03-29 陕西师范大学 Benzofuran luminescent liquid crystal compound and synthetic method and application thereof

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