CN103058947B - Liquid crystalline cpd containing the sub-methoxyl group bridge of benzoxazole and difluoro and preparation method thereof and application - Google Patents
Liquid crystalline cpd containing the sub-methoxyl group bridge of benzoxazole and difluoro and preparation method thereof and application Download PDFInfo
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Abstract
The invention discloses a kind of containing benzoxazole and the sub-methoxyl group bridge of difluoro (-CF
2o-) liquid crystalline cpd and preparation method thereof and application.The general structure of this compound is such as formula shown in I.This compound structure is more stable, there is wide liquid crystal state temperature range, good low temperature intersolubility, larger positive dielectric anisotropy △ ε, optics can realize lower threshold voltage when using, with low rotary viscosity γ, liquid-crystal composition material and display performance can be improved, significant to the quick response realizing indicating meter.It is low that liquid-crystal composition containing this compounds can be applicable to prepare driving voltage, wide temperature range, the liquid-crystal display of fast response time.
Description
Technical field
The invention belongs to liquid crystalline cpd and Application Areas, relate to a kind of containing benzoxazole and the sub-methoxyl group bridge of difluoro (-CF
2o-) liquid crystalline cpd and preparation method thereof and application.
Background technology
For technical field of liquid crystal display, although market is very huge in recent years, technology is also ripe gradually, and people also in continuous raising, especially in realization response fast, reduce driving voltage to reduce the aspects such as power consumption to the requirement of technique of display.Liquid crystal material as one of important photoelectron material of liquid-crystal display, the effect important to the performance improving liquid-crystal display.
Liquid crystal material as display obtains and develops on a large scale very much, has occurred a large amount of liquid crystalline cpds.Develop into phenylcyclohexane class, phenylacetylene class, ethyl bridged bond class, end thiazolinyl liquid crystal and various fluorine-containing aromatic ring class liquid crystalline cpds etc. from biphenyl nitrile, ester class, oxygen heterocyclic ring class, pyrimidine lopps liquid crystalline cpd, constantly meet the display performance requirements such as TN, STN, TFT-LCD.
Any display liquid crystal all requires suitable temperature range, wider liquid crystal state temperature, and higher stability, than better suited viscosity, has response speed faster to electric field.But also use in a liquid crystal display separately without any single liquid crystal monomer so far, and just need not can meet performance requriements with other compound combination
Summary of the invention
The object of this invention is to provide a kind of containing benzoxazole and the sub-methoxyl group bridge of difluoro (-CF
2o-) liquid crystalline cpd and preparation method thereof and application.
Provided by the invention containing benzoxazole and the sub-methoxyl group bridge of difluoro (-CF
2o-) liquid crystalline cpd is also compound shown in formula I,
Formula I
In described formula I, R
1and R
2for group shown in following A or B:
A, be selected from H, CL, F ,-CN ,-OCN, OCF
3, CF
3, CHF
2, OCHF
2,-SCN ,-NCS ,-SF
5, at least one in the alkoxyl group of C1-C15 that replaces of the alkyl of C1-C15, the fluorine or chlorine alkyl of C1-C15, the alkoxyl group of C1-C15 and the fluorine or chlorine that replace;
B, by least one non-conterminous-CH in described A
2-substituted by least one in-CH=CH-,-C ≡ C-,-COO-,-OOC-, tetramethylene and-O-and the group that obtains;
Described A
1, A
2, A
3and A
4all be selected from least one in singly-bound and following radicals:
L
1, L
2and L
3all be selected from singly-bound ,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-,-CH
2cH
2-,-CF
2cH
2-,-CH
2cF
2-,-C
2f
4-,-CF=CF-and-(CH
2)
4-at least one;
A, b and c are the integer of 0-3, and a+b+c≤5.
Concrete, compound shown in described formula I is compound shown in formula Ia,
Formula I a
In described formula I a, R
1, R
2, A
1, A
4, A
2, A
3and L
1definition identical with claim 1;
A is the integer of 0-3; B and c is the integer of 1-3, and a+b+c≤4.
More specifically, compound shown in described formula I is for as shown in the formula compound shown in I 1 to I 10:
Wherein, R
1for straight chained alkyl or alkoxyl group that hydrogen, carbonatoms are 1 ~ 10 ,-(F) represents phenyl ring there is fluorine atom substituent or is hydrogen.
Described formula I R
1and R
2definition in, in the alkoxyl group of the C1-C15 that the alkyl of C1-C15, the alkoxyl group of C1-C15 and fluorine or chlorine that the alkyl of described C1-C15, fluorine or chlorine replace replace, the carbon atom of alkyl or alkoxyl group is specially 1-10 or 1-8 or 1-6 or 1-5 or 1-4 or 1-3 or 2-5 or 2-4 or 2-8.
Described in preparation formula I provided by the invention, the method for compound, comprises the steps:
1) will
with triethylamine in 5-10 DEG C with
after mixing, be warming up to 20 ~ 80 DEG C and carry out ring closure reaction 1 ~ 5 hour, react complete and obtain
2) by step 1) gained
mix with n-Butyl Lithium, and it is saturated to system to pass into carbonic acid gas, carries out addition reaction, react complete and obtain
3) by step 2) gained
reflux dewatering reaction is carried out in 1,3-dimercaptopropane and trifluoromethanesulfonic acid mixing, separates the water of generation, after point water purification, cools and obtain
4) will
with triethylamine in-50 ~-90 DEG C and step 3) gained
after mixing carries out reaction 0.5-2 hour, temperature is kept to add NEt successively again
3fluoridation 1-3 hour is carried out in 3HF and bromine mixing, reacts complete and obtains compound shown in described formula I;
Described step 1) in step 4) reaction materil structure formula, R
1, R
2, A
1, A
2, A
3, A
4, L
1, L
2, a and b definition as hereinbefore.
The synthetic route of the method is as follows:
In described step 1),
triethylamine with
molar ratio be 0.8-1.2:1-3:0.8-1.8, preferred 1:2:1.1;
Described step 2) in, described in
be 1-1.2:1-1.5 with the molar ratio of n-Butyl Lithium, preferred 1:1;
In described addition reaction step, temperature is-50 ~-90 DEG C, and preferably-70 DEG C, the time is 0.5-3 hour, preferably 2 hours;
In described step 3),
the mole dosage ratio that feeds intake of 1,3-dimercaptopropane and trifluoromethanesulfonic acid is 0.8-1.2:0.9-1.3:1.0-1.5, preferred 1.0:1.1:1.2;
In described step 4),
triethylamine,
nEt
3the mole dosage ratio that feeds intake of 3HF and bromine is 0.8-1.2:0.8-1.2:0.8-1.2:2.5-6:2.5-6, preferred 1:1:1:4:4;
Described step 1)-4) reactions steps carries out all in a solvent; Described solvent is selected from least one in tetrahydrofuran (THF), toluene, Virahol and methylene dichloride.
The compound of structural formula I is due to substituent difference, and thus range of application is more extensive.These compounds can as the basic ingredient of liquid crystal compound.Therefore be also at least one in compound shown in described formula I containing component A() liquid crystal compound, also belong to protection scope of the present invention, wherein, compound described in formula I is 1-5 kind, preferred 2-4 kind; Described component A accounts for the 1-90% of described liquid crystal compound gross weight, preferred 5-60%, more preferably 10-40%, is more specifically 13% or 26% or 13-26%.
Concrete, described component A is made up of any two kinds in compound shown in formula I1, and its mass ratio is 7-12:6-14 or 7:6 or 12:14;
Shown in described formula I1, compound is specially
It is 7:6's that described component A is specially by mass ratio
composition,
Or be 12:14's by mass ratio
composition;
The described liquid crystal compound containing component A is specially liquid crystal compound a or b:
Wherein, liquid crystal compound a is made up of each component of following structural formula and mass parts:
Liquid crystal compound b is made up of each component of following structural formula and mass parts:
The application in liquid crystal display material or electrooptics display material prepared by compound shown in above-mentioned formula I or described liquid crystal compound, and the liquid crystal display material of compound or described liquid crystal compound shown in contained I or electrooptics liquid-crystal display.Wherein, described indicating meter is TN indicating meter, STN indicating meter or IPS indicating meter.
Containing benzoxazole and the sub-methoxyl group bridge of difluoro (-CF in molecular structure of compounds shown in formula I provided by the invention
2o-), there is good stability, larger △ n, larger positive dielectric anisotropy △ ε, when using in optics, lower threshold voltage can be realized, also there is wide nematic phase range and low rotary viscosity γ simultaneously
1, significant for the quick response realizing indicating meter, therefore be suitable for very much allocating liquid crystal compound.Optics can realize lower threshold voltage when using, and low rotary viscosity γ, can improve liquid-crystal composition material and display performance, significant to the quick response realizing indicating meter.It is low that liquid-crystal composition containing this compounds can be applicable to prepare driving voltage, wide temperature range, the liquid-crystal display of fast response time.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described material all can obtain from open commercial sources if no special instructions.
Below in embodiment:
1, GC represents gas chromatographic purity (Agilent HP6820 type gas chromatographicanalyzer)
2, MS represents mass spectrum (Agilent MS5975C type)
3,1H-NMR represents nucleus magnetic hydrogen spectrum
4, MP represents fusing point (the micro-thermal analyzer of WRX-1S, setting temperature rise rate is 3 DEG C/min)
5, CP represents that (scanner is turned round in plum Teller DSC822e type differential calorimetric to clearing point, heats up or cooling rate 1 DEG C/min; Plum Teller FP-52 type polarizing microscope melting point apparatus, heat-up rate 3 DEG C/min)
6, △ ε represents dielectric anisotropy (20 DEG C, 1000Hz, Hewlett-Packard HP4284a), △ ε=ε
11-ε
⊥(ε
11for liquid crystal molecule is at the specific inductivity of long axis direction, ε
⊥for liquid crystal molecule is at the specific inductivity of short-axis direction)
7, △ n represents optical anisotropy (20 DEG C, 589nm, Abbérefractometer), △ n=n
11-n
⊥(specific refractory power (n
11) be measure when polarization direction is parallel with frictional direction, specific refractory power (n
⊥) be measure when polarization direction is vertical with frictional direction)
Embodiment 1
Step 1:
0.2mol 4-propyl group Ortho-Aminophenol (reactant) is added in reaction flask, 0.2mol triethylamine (reactant), 1000ml N, N-METHYLFORMAMIDE (solvent), is cooled to 10 DEG C, drips 0.22mol 3 in 1 hour, 5-difluoro benzoyl chloride (reactant), drip and finish, be warming up to 50 DEG C, carry out ring closure reaction 3 hours.300ml water is added in reaction solution, separatory, extract aqueous phase 2 times with 100ml toluene (solvent), united extraction liquid, is washed to neutrality, add 10g tosic acid (catalyzer) and 200ml toluene (solvent), be heated with stirring to reflux water-dividing 4 hours, reaction mixture be washed to neutrality, solvent evaporated, cross silica gel (discoloring agent) post after dissolving with sherwood oil (solvent), after solvent evaporated, obtain white needle-like crystals (1-a).Yield 70%, gas chromatographic purity 98.5%.
Step 2:
Add in reaction flask 0.1mol (1-a) (reactant) that step obtains, 120ml tetrahydrofuran (THF) (solvent), sealing is installed stir, logical nitrogen replacement air, be cooled to-70 DEG C, drip the hexane solution that 0.1mol concentration is the n-Butyl Lithium (reactant) of 2.5M, add latter 20 minutes, pass into dry carbon dioxide (reactant), to saturated, carry out addition reaction at this temperature and react complete after 2 hours, this reaction solution is poured in the beaker of 20ml concentrated hydrochloric acid (adjust ph) and 100ml water and be hydrolyzed, separatory, 50ml ethyl acetate (solvent) extracts aqueous phase once, merge organic phase, saturated common salt is washed to neutrality, anhydrous sodium sulphate (siccative) is dry, concentrate and eliminate solvent, obtain light yellow solid, with Virahol (solvent) recrystallization once, obtain white crystal (1-b).Yield 90%, liquid chromatography purity 98.0%.
Step 3:
0.1mol (1-b) is added in reaction flask, 30ml toluene (solvent) and 30ml octane-iso (solvent), add 14g1, 3-dimercaptopropane (reactant) (0.13mol), under stirring, above-mentioned suspension is heated to 50 DEG C, trifluoromethanesulfonic acid (reactant) 19.2g(0.128mol is added) in 30 minutes, backflow is warming up to after adding, separate the water of generation, after point water purification, cool to 90 DEG C, methyl tertiary butyl ether (solvent) 100ml is added in 45 minutes between 70-90 DEG C, continue cooling, crystallize out, filter under nitrogen protection, crystal methyl tertiary butyl ether (solvent) (25ml × 4) washing obtained, vacuum-drying obtains orange crystal (dithiane fluoroform sulphonate) (1-c).
Step 4:
0.1mol 3 is added in reaction flask, 4,5-trifluoromethyl phenol (reactant), the mixing solutions of 0.1mol triethylamine (reactant) and 130ml methylene dichloride (solvent) is also cooled to-70 DEG C, drip the solution of the 120ml methylene dichloride (solvent) of above-mentioned 0.1mol (1-c) crystal (reactant), within 45 minutes, add, stir in this temperature and carry out reaction after 1 hour, in 5 minutes, add 0.4mol NEt33HF(reactant).Then at-70 DEG C, 30ml methylene dichloride (solvent) solution of 0.4mol bromine (reactant) is added in 1 hour, then at-70 DEG C, continue fluoridation react complete after 1 hour, be warming up to 0 DEG C again, in the 160ml aqueous sodium hydroxide solution (adjust ph) reaction solution being poured into 32% and 300g ice, regulate pH value to 5 ~ 8 of reaction solution by dripping 45g32% aqueous sodium hydroxide solution.After separatory, aqueous phase 80ml methylene dichloride (solvent) extracts, and merges organic phase 4g diatomite (discoloring agent) and filters, washing, the lower solvent evaporated of decompression.Sherwood oil (solvent) recrystallization after the crude product column chromatography obtained, obtains white crystal product (1-d), yield 45%,
Experimental result is as follows:
1、GC：99.5%。
2、MS：m/s%146(11.04)162(8.84)188(5.66)293(20.57)322(100)469(5.87)
3、MP：75℃
As from the foregoing, this product structure is correct, is compound shown in formula I1.Its liquid crystal property detected result is as follows:
4、△ε：20.0V（20℃，1000Hz）
5、△n：0.2（20℃，589nm）
6、CP：109℃
Embodiment 2
According to 4 steps reactions of embodiment 1,3,5-difluoro benzoyl chlorides in step 1 are replaced with a fluorobenzoyl chloride, and product feeds intake downwards reaction successively, and 3,4,5-trifluoromethyl phenols in step 4 replace with 3,4-difluorophenol and prepare compound shown in following formula I2.
Wherein, each step intermediate is respectively
Step 1
Step 2
Step 3
Step 4
Experimental result is as follows:
1、GC：99.6%
2、MS：m/z%139(2.77)182(3.41)225(9.94)319(100)433(M
+0.66)
3、MP：79.5℃
As from the foregoing, this product structure is correct, is compound shown in formula I1.Its liquid crystal property detected result is as follows:
4、△ε：14.3（20℃，1000Hz）
5、△n：0.109（20℃，589nm）
6、CP：119.5℃
Embodiment 3 ~ 35
With reference to the method for embodiment 1,2, only reactant substituting group is carried out corresponding replacement according to the substituting group in product, obtains as shown in the formula compound shown in I:
Embodiment 36
By embodiment 1 gained
with embodiment 2 gained
and the liquid crystalline cpd of other following structural formulas, mix according to following weight ratio, obtain liquid crystal compound:
Physical property and the liquid crystal property detected result of this mixture are as follows:
CP=95℃
Δn=0.100
Δε=6.9。
And add embodiment 1 gained
with embodiment 2 gained
before, the physical property of the liquid crystal compound of above-mentioned mass ratio and liquid crystal property detected result as follows:
CP=85℃
Δn=0.086
Δε=4.8。
As from the foregoing, formula I adds in liquid crystal compound, significantly can improve the performance of liquid crystal compound, significantly improves dielectric anisotropy Δ ε and optical anisotropy Δ n, improves degree of birefringence, widened the nematic temperature range of liquid crystal compound.
Embodiment 37
By embodiment 1 gained
with embodiment 4 gained
and the liquid crystalline cpd of other following structural formulas, mix according to following weight ratio, obtain liquid crystal compound:
Physical property and the liquid crystal property detected result of this mixture are as follows:
CP=92℃
Δn=0.103
Δε=8.3。
And add embodiment 1 gained
with embodiment 4 gained
before, the physical property of the liquid crystal compound of above-mentioned mass ratio and liquid crystal property detected result as follows:
CP=80℃
Δn=0.080
Δε=4.7。
As from the foregoing, formula I adds in liquid crystal compound, significantly can improve the performance of liquid crystal compound, significantly improves dielectric anisotropy Δ ε and optical anisotropy Δ n, improves degree of birefringence, widened the nematic temperature range of liquid crystal compound.
Claims (9)
1. compound shown in formula I,
In described formula I, R
1for carbonatoms is the straight chained alkyl of 1 ~ 10.
2. prepare a method for compound described in claim 1, comprise the steps:
1) will
with triethylamine in 5-10 DEG C with
after mixing, be warming up to 20 ~ 80 DEG C and carry out ring closure reaction 1 ~ 5 hour, react complete and obtain
2) by step 1) gained
mix with n-Butyl Lithium, and it is saturated to system to pass into carbonic acid gas, carries out addition reaction, react complete and obtain
3) by step 2) gained
reflux dewatering reaction is carried out in 1,3-dimercaptopropane and trifluoromethanesulfonic acid mixing, separates the water of generation, after point water purification, cools and obtain
4) will
with triethylamine in-50 ~-90 DEG C and step 3) gained
after mixing carries out reaction 0.5-2 hour, temperature is kept to add NEt successively again
3fluoridation 1-3 hour is carried out in 3HF and bromine mixing, reacts complete and obtains compound shown in described formula I;
Described step 1) to step 4) in reaction materil structure formula, R
1definition identical with claim 1.
3. method according to claim 2, is characterized in that: described step 1) in,
triethylamine with
molar ratio be 0.8-1.2:1-3:0.8-1.8; Or,
Described step 2) in, described in
be 1-1.2:1-1.5 with the molar ratio of n-Butyl Lithium; Or in described addition reaction step, temperature is-50 ~-90 DEG C, and the time is 0.5-3 hour; Or,
Described step 3) in,
the mole dosage ratio that feeds intake of 1,3-dimercaptopropane and trifluoromethanesulfonic acid is 0.8-1.2:0.9-1.3:1.0-1.5; Or,
Described step 4) in,
triethylamine,
nEt
3the mole dosage ratio that feeds intake of 3HF and bromine is 0.8-1.2:0.8-1.2:0.8-1.2:2.5-6:2.5-6.
4. according to the method in claim 2 or 3, it is characterized in that: described step 1)-4) reactions steps carries out all in a solvent; Described solvent is specifically selected from least one in tetrahydrofuran (THF), toluene, Virahol and methylene dichloride.
5. the liquid crystal compound containing component A; Described component A is at least one in compound shown in formula I described in claim 1.
6. liquid crystal compound according to claim 5, is characterized in that: described component A is 1-5 kind compound;
Described component A accounts for the 1-90% of described liquid crystal compound gross weight.
7. liquid crystal compound according to claim 6, is characterized in that: described component A is 2-4 kind compound;
Described component A accounts for the 10-40% of described liquid crystal compound gross weight.
8. the application in liquid crystal display material or electrooptics display material prepared by liquid crystal compound according to any one of compound described in claim 1 or claim 5-7.
9. comprise the liquid crystal display material in liquid crystal compound described in compound described in claim 1 or claim 6 or 7 or electrooptics liquid-crystal display.
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| CN103409146B (en) * | 2013-04-01 | 2015-10-28 | 石家庄诚志永华显示材料有限公司 | For the liquid-crystal composition of driven with active matrix liquid-crystal display |
| CN103254903B (en) * | 2013-04-27 | 2016-04-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystalline cpd containing difluoro methylene key bridge and preparation method thereof and composition |
| CN108530374B (en) * | 2018-06-05 | 2019-12-17 | 大连理工大学 | Preparation method for synthesizing 2-mercaptobenzoxazole (thiadiazole) compound based on 1, 3-propanedithiol as mercapto source |
| CN110437846B (en) * | 2019-08-30 | 2022-02-25 | 陕西师范大学 | Fluorine substituted benzoxazole liquid crystal compound containing acetylene bond and preparation method thereof |
| CN111607411A (en) * | 2020-06-17 | 2020-09-01 | 华南师范大学 | Difluoromethoxyl liquid crystal compound containing benzoxazole heterocycle, and synthesis method and application thereof |
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| CN1411455A (en) * | 2000-03-03 | 2003-04-16 | 默克专利股份公司 | Method for producing liquid crystals with CF20 bond |
| CN1504464A (en) * | 2002-11-29 | 2004-06-16 | 石家庄实力克液晶材料有限公司 | 2,5-substituted benzoxazole derivative, preparing process and uses thereof |
| CN1507427A (en) * | 2001-07-20 | 2004-06-23 | Ĭ��ר���ɷ�����˾ | Indane compounds with negative dielectric anisotropy |
| DE102004053279A1 (en) * | 2003-11-25 | 2005-06-23 | Merck Patent Gmbh | Benzofuran and benzothiophene derivatives, useful as components of liquid crystal media for electro-optical display devices are new |
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|---|---|---|---|---|
| CN1411455A (en) * | 2000-03-03 | 2003-04-16 | 默克专利股份公司 | Method for producing liquid crystals with CF20 bond |
| CN1507427A (en) * | 2001-07-20 | 2004-06-23 | Ĭ��ר���ɷ�����˾ | Indane compounds with negative dielectric anisotropy |
| CN1504464A (en) * | 2002-11-29 | 2004-06-16 | 石家庄实力克液晶材料有限公司 | 2,5-substituted benzoxazole derivative, preparing process and uses thereof |
| DE102004053279A1 (en) * | 2003-11-25 | 2005-06-23 | Merck Patent Gmbh | Benzofuran and benzothiophene derivatives, useful as components of liquid crystal media for electro-optical display devices are new |
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Effective date of registration: 20190424 Address after: Room 601-1, 6th floor, Tsinghua Tongfang Building, Tsinghua Garden, Haidian District, Beijing Patentee after: Beijing Chengzhi Yonghua Display Technology Co., Ltd. Address before: 050091 No. 362 Xinshi North Road, Shijiazhuang City, Hebei Province Patentee before: Shijiazhuang Chengzhi Yonghua Display Materials Co., Ltd. |
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Address after: Room b402, block B, 4th floor, building 1, yard 1, Zhongguancun East Road, Haidian District, Beijing 100084 Patentee after: Beijing Chengzhi Yonghua Technology Co.,Ltd. Address before: Room 601-1, 6th floor, Tsinghua Tongfang Building, Tsinghua Garden, Haidian District, Beijing Patentee before: BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY Co.,Ltd. |