CN1762946A - Alkylcyclohexyl multiple-fluorine biphenyl derivative and its preparation method and uses - Google Patents
Alkylcyclohexyl multiple-fluorine biphenyl derivative and its preparation method and uses Download PDFInfo
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- CN1762946A CN1762946A CN 200510109068 CN200510109068A CN1762946A CN 1762946 A CN1762946 A CN 1762946A CN 200510109068 CN200510109068 CN 200510109068 CN 200510109068 A CN200510109068 A CN 200510109068A CN 1762946 A CN1762946 A CN 1762946A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 229910052731 fluorine Inorganic materials 0.000 title claims description 24
- 239000011737 fluorine Substances 0.000 title claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 67
- 239000004305 biphenyl Substances 0.000 claims abstract description 34
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000004327 boric acid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 6
- DNXSLLIDTGLIHX-UHFFFAOYSA-N 1-bromo-3,4-difluoro-2-methoxybenzene Chemical compound COC1=C(F)C(F)=CC=C1Br DNXSLLIDTGLIHX-UHFFFAOYSA-N 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000012769 display material Substances 0.000 claims description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 235000010338 boric acid Nutrition 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 125000005619 boric acid group Chemical class 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical class FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 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 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 methoxyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The present invention discloses the preparation process and application of derivative alkyl cyclohexyl diphenyl polyfluoride. The derivative alkyl cyclohexyl diphenyl polyfluoride is used as liquid crystal material. It has methoxyl radical with small volume, small dipole moment and average dipole direction in major molecular axis direction introduced to the side of its diphenyl ring, and thus has increased dielectric anisotropy in the major molecular axis direction, lowered melting point and increased dissolubility. In addition, the multiple fluorine atoms are favorable to the increase of the dielectric anisotropy and the decrease of liquid crystal driving voltage. Therefore, the derivative of the present invention has excellent application foreground in LCD field.
Description
Technical field
The present invention relates to compound and preparation method thereof and application, particularly relate to a kind of alkylcyclohexyl multiple-fluorine biphenyl derivative and preparation method thereof, and this compound is in Application in LCD.
Background technology
Develop rapidly along with TFT liquid-crystal display (Thin Solid Film), requirement to the high-performance liquid crystal material is more and more urgent, especially for obtaining wideer operating temperature range, reduce driving voltage, realize the reduce power consumption of display device, the development dielectric anisotropy is big, and fusing point is low, and the wide high-performance liquid crystal material of mesomorphic temperature range is TFT with liquid crystal material research direction from now on.
Cyclohexyl polyfluoro biphenyls liquid crystal compounds is owing to have good heat, chemical stability, high electric charge conservation rate, and high resistivity, low viscosity etc. have been widely used in the TFT liquid-crystal display.The PlachHerbert of Germany Merck company etc. will have
The liquid crystalline cpd of structure is applied to (DE4139553,1992) in the mixed liquid crystal; Japan Dainippon Inc﹠amp; The Takehara Sadao of Chemicals company etc. will have
The liquid crystalline cpd of structure is applied to (JP 8183749,1996) in the mixed liquid crystal; The Hideo Ichinose of Germany Merck company etc. will have
The liquid crystalline cpd of structure is applied to (GB 2310428,1997) in the mixed liquid crystal, and all these materials have all shown good physicals.
Summary of the invention
The purpose of this invention is to provide a kind of alkylcyclohexyl multiple-fluorine biphenyl class liquid crystal and preparation method thereof.
Alkylcyclohexyl multiple-fluorine biphenyl class liquid crystal derived thing provided by the present invention, its structural formula is formula I,
Formula (I)
Wherein, R is that carbonatoms is 1～10 straight or branched alkyl; A is H or F.
More specifically, alkylcyclohexyl multiple-fluorine biphenyl derivative of the present invention comprises:
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl.
The preparation method of The compounds of this invention has two kinds of technical schemes:
Scheme one comprises the steps: 1) preparation 3,4-difluoro-2-methoxy boric acid: with 3,4-difluoro-2-methoxyl bromobenzene and MAGNESIUM METAL reaction generate Grignard reagent, with the trimethyl borate reaction, obtain structural formula after the hydrolysis suc as formula 3 of II, 4-difluoro-2-methoxy boric acid then; 2) preparation alkylcyclohexyl multiple-fluorine biphenyl derivative: suc as formula 3 of II, the compound of 4-difluoro-2-methoxy boric acid and structural formula such as formula III carries out linked reaction under catalyst action with structural formula, obtain described 3, the 4-difluoro-2-methoxyl biphenyl derivative; Described catalyzer is that four (triphenylphosphines) close palladium;
Wherein, step 2) temperature of described linked reaction is 60-90 ℃, and reaction solvent is benzene and dehydrated alcohol.
Reaction equation is as follows:
Wherein, the definition of R, A is identical with formula I.
Scheme two comprises the steps: 1) the preparation structural formula is the compound of formula IV: with structural formula is that compound and the MAGNESIUM METAL reaction of formula III generates Grignard reagent, reacts with trimethyl borate then, obtains the compound that structural formula is formula IV after the hydrolysis; 2) preparation alkylcyclohexyl multiple-fluorine biphenyl derivative: with structural formula be the compound of formula IV and structural formula suc as formula 3 of V, 4-difluoro-2-methoxyl bromobenzene carries out linked reaction under catalyst action, obtain described alkylcyclohexyl multiple-fluorine biphenyl derivative; Described catalyzer is that four (triphenylphosphines) close palladium;
Formula (IV)
Wherein, step 2) temperature of reaction of described linked reaction is 60-90 ℃, and reaction solvent is benzene and dehydrated alcohol.
Reaction equation is as follows:
Wherein, the definition of R, A is identical with formula (I).
Another object of the present invention provides the purposes of The compounds of this invention.
It is big that The compounds of this invention has a Δ ε; fusing point is low, and fat-soluble advantage such as good is a kind of well behaved liquid crystal display material; therefore, be that the liquid crystal display material of main component also belongs to protection scope of the present invention with alkylcyclohexyl multiple-fluorine biphenyl derivative of the present invention.
The compounds of this invention has been introduced methoxyl group on the side direction of cyclohexyl biphenyl, because such group spatial volume is less, little and the average dipole direction of galvanic couple distance is in the molecular long axis direction, so help increasing the dielectric anisotropy of compound molecule in the molecular long axis direction, reduce the fusing point of material, increase solvability, in addition, the existence of a plurality of fluorine atoms also helps increasing the dielectric anisotropy of compound molecule in the molecular long axis direction, thereby reduce the driving voltage of liquid crystal material, such material has good prospects for application in field of liquid crystal display.
Embodiment
Embodiment 1, preparation 4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
1, preparation 3,4-difluoro-2-methoxy boric acid
In the 250ml there-necked flask, add 22.3g (0.1mol) 3,4-difluoro-2-methoxyl bromobenzene, the 50ml tetrahydrofuran (THF), 2.43g (0.1mol) MAGNESIUM METAL and 1～2 iodine, stirring reaction 1 hour after the initiation reaction at room temperature, system temperature is reduced to-70 ℃ with ethanol-liquid nitrogen system then, under this temperature, slowly drip 10.4g (0.1mol) trimethyl borate, dropwising the back makes it rise to room temperature naturally under agitation condition, dripping 10% HCl solution to pH value then is 1, is heated to 100 ℃ and refluxes 1 hour down.With behind the petroleum ether extraction water of 100ml * 3, use the saturated common salt water washing again reaction solution cooling back, spend the night with anhydrous sodium sulfate drying to neutral.Dried solution revolved steam solution, obtain 15.9g 3,4-difluoro-2-methoxy boric acid, yield 85%.
2, preparation 4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
In the 500ml there-necked flask, add 15.9g (0.085mol) 3,4-difluoro-2-methoxy boric acid, 27.8g (0.085mol) 4-(4 '-trans-amyl group cyclohexyl)-2-fluoro-bromobenzene, 150ml benzene, the 60ml dehydrated alcohol, 25g yellow soda ash, 6.6g water and 1.96g four (triphenylphosphine) close palladium, are heated to 70 ℃ of 24 hours postcooling that reflux down to room temperature.Tell organic phase,, merge the organic phase after washing, use anhydrous sodium sulfate drying to neutral with 100ml * 3 chloroform extraction waters.Dried solution revolved steam solution, obtain white crude product 29g, use the dehydrated alcohol recrystallization, obtain the white crystal of 20.6g 4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls, yield 62%.
45.9 ℃ of I of DSC (differential scanning calorimeter): Cr
IR (wave number/cm
-)
1: 3010,2947,2854,1876,1614,1595,1568,1491,1475,1412,1367,1310,1281,1240,1178,1132,1080,1041,955,943,864,812,762,669,627,613,538
MS：390(M
+)，375，319，279，278，265，264，251，247，237，219，201，183，175，153，143，109，97，95，83，81，71，69，57，55，43
The proof products therefrom is correct.
Can obtain with identical method:
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls.
Embodiment 2,4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl
1, preparation 4-(trans-4 '-propyl group cyclohexyl)-2,6-two fluoro-phenylo boric acids
In the 250ml there-necked flask, add 31.7g (0.1mol) 4-(trans-4 '-propyl group cyclohexyl)-2,6-two fluoro-bromobenzenes, the 100ml tetrahydrofuran (THF), 2.43g (0.1mol) MAGNESIUM METAL and 1～2 iodine, at room temperature stirred 1 hour after the initiation reaction, system temperature is reduced to-70 ℃ with ethanol-liquid nitrogen system then, under this temperature, slowly drip 10.4g (0.1mol) trimethyl borate, dropwising the back makes it rise to room temperature naturally under agitation condition, dripping 10% HCl solution to pH value then is 1, is heated to 100 ℃ and refluxes 1 hour down.With behind the petroleum ether extraction water of 100ml * 3, use the saturated common salt water washing again reaction solution cooling back, spend the night with anhydrous sodium sulfate drying to neutral.Dried solution revolved steam solution, obtain 19.8g4-(trans-4 '-propyl group cyclohexyl)-2,6-two fluoro-phenylo boric acids, yield 70%.
2,4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl
In the 250ml there-necked flask, add 11.3g (0.04mol) 4-(trans-4 '-propyl group cyclohexyl)-2,6-two fluoro-phenylo boric acids, 9.0g (0.04mol) 3,4-difluoro-2-methoxyl bromobenzene, 100ml benzene, 50ml dehydrated alcohol, 12g yellow soda ash, 4g water and 0.95g four (triphenylphosphine) close palladium, are heated to 70 ℃ of 24 hours postcooling that reflux down to room temperature.Tell organic phase,, merge the organic phase after washing, use anhydrous sodium sulfate drying to neutral with 100ml * 3 chloroform extraction waters.Dried solution revolved steam solution, obtain white crude product 13.9g, use the dehydrated alcohol recrystallization, obtain 10.5g4 '-(4 "-trans-propyl group cyclohexyl)-3,4, the white crystal of 2 ', 6 '-tetrafluoro-2-methoxyl biphenyl, yield 69%.
54.5 ℃ of NI of DSC (differential scanning calorimeter): Cr
IR: wave number/cm
-1=3010,2958,2860,1865,1615,1585,1560,1486,1475,1420,1387,1315,1285,1238,1175,1128,1080,965,945,860,813,772,658,627,615,540
MS(m/z)：380(M
+)，337，322，311，297，296，283，282，269，255，237，219，201，193，188，155，143，127，109，95，85，81，69，55，43
Proof gained compound is correct.
Can obtain with identical method:
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl.
Claims (7)
1, alkylcyclohexyl multiple-fluorine biphenyl derivative, its structural formula are formula I
Formula (I)
Wherein, R is that carbonatoms is 1～10 straight or branched alkyl; A is H or F.
2, alkylcyclohexyl multiple-fluorine biphenyl derivative according to claim 1 is characterized in that: described alkylcyclohexyl multiple-fluorine biphenyl derivative is:
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 '-three fluoro-2-methoxyl biphenyls,
4 '-(4 "-trans-methylcyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-ethyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-propyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-butyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-amyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-hexyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-heptyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-octyl group cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-nonyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl,
4 '-(4 "-trans-decyl cyclohexyl)-3,4,2 ', 6 '-tetrafluoro-2-methoxyl biphenyl.
3, the preparation method of the described alkylcyclohexyl multiple-fluorine biphenyl derivative of claim 1, comprise the steps: 1) preparation 3,4-difluoro-2-methoxy boric acid: with 3,4-difluoro-2-methoxyl bromobenzene and MAGNESIUM METAL reaction generate Grignard reagent, react with trimethyl borate then, obtain structural formula after the hydrolysis suc as formula 3 of II, 4-difluoro-2-methoxy boric acid; 2) preparation alkylcyclohexyl multiple-fluorine biphenyl derivative: suc as formula 3 of II, the compound of 4-difluoro-2-methoxy boric acid and structural formula such as formula III carries out linked reaction under catalyst action, obtain described alkylcyclohexyl multiple-fluorine biphenyl derivative with structural formula; Described catalyzer is that four (triphenylphosphines) close palladium;
Formula (II)
Formula (III)
Wherein, R is that carbonatoms is 1～10 alkyl; A is H or F.
4, preparation method according to claim 3 is characterized in that: step 2) temperature of described linked reaction is 60-90 ℃, reaction solvent is benzene and dehydrated alcohol.
5, the preparation method of the described alkylcyclohexyl multiple-fluorine biphenyl derivative of claim 1, comprising the steps: 1) the preparation structural formula is the compound of formula IV: with structural formula compound and the MAGNESIUM METAL reaction generation Grignard reagent of formula III, with the trimethyl borate reaction, obtain the compound that structural formula is formula IV after the hydrolysis then; 2) preparation alkylcyclohexyl multiple-fluorine biphenyl derivative: with structural formula be the compound of formula IV and structural formula suc as formula 3 of V, 4-difluoro-2-methoxyl bromobenzene carries out linked reaction under catalyst action, obtain described alkylcyclohexyl multiple-fluorine biphenyl derivative; Described catalyzer is that four (triphenylphosphines) close palladium;
Formula (IV)
Wherein, R is that carbonatoms is 1～10 alkyl; A is H or F.
6, it is characterized in that: step 2) temperature of reaction of described linked reaction is 60-90 ℃, reaction solvent is benzene and dehydrated alcohol.
7, the application of the arbitrary described alkylcyclohexyl multiple-fluorine biphenyl derivative of claim 1-2 in the preparation liquid crystal display material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101090684A CN100391923C (en) | 2005-10-17 | 2005-10-17 | Alkylcyclohexyl multiple-fluorine biphenyl derivative and its preparation method and uses |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101090684A CN100391923C (en) | 2005-10-17 | 2005-10-17 | Alkylcyclohexyl multiple-fluorine biphenyl derivative and its preparation method and uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1762946A true CN1762946A (en) | 2006-04-26 |
| CN100391923C CN100391923C (en) | 2008-06-04 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101948372B (en) * | 2010-01-11 | 2012-07-04 | 清华大学 | 2-methoxyl-3,4-difluorobenzene, preparation method and application thereof |
| CN101768055B (en) * | 2010-01-18 | 2013-03-27 | 清华大学 | Liquid crystal compound and preparation method thereof |
| CN101580716B (en) * | 2008-05-15 | 2013-04-17 | 石家庄诚志永华显示材料有限公司 | Terminal isothiocyano liquid-crystal compound containing pyrimidine ring and preparation method thereof |
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2005
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101580716B (en) * | 2008-05-15 | 2013-04-17 | 石家庄诚志永华显示材料有限公司 | Terminal isothiocyano liquid-crystal compound containing pyrimidine ring and preparation method thereof |
| CN101948372B (en) * | 2010-01-11 | 2012-07-04 | 清华大学 | 2-methoxyl-3,4-difluorobenzene, preparation method and application thereof |
| CN101768055B (en) * | 2010-01-18 | 2013-03-27 | 清华大学 | Liquid crystal compound and preparation method thereof |
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