CN109370609B - Liquid crystal composition for VA-LCD (vertical alignment-liquid Crystal display) with low threshold, low power consumption, low viscosity and quick response - Google Patents
Liquid crystal composition for VA-LCD (vertical alignment-liquid Crystal display) with low threshold, low power consumption, low viscosity and quick response Download PDFInfo
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- CN109370609B CN109370609B CN201811168306.2A CN201811168306A CN109370609B CN 109370609 B CN109370609 B CN 109370609B CN 201811168306 A CN201811168306 A CN 201811168306A CN 109370609 B CN109370609 B CN 109370609B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 230000004044 response Effects 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- -1 4-substituted phenylene group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- JZVHTGXKGZSUFC-UHFFFAOYSA-N 2-(4-ethoxy-2,3-difluorophenyl)acetaldehyde Chemical compound CCOC1=CC=C(CC=O)C(F)=C1F JZVHTGXKGZSUFC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000006750 UV protection Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- RAYQDNSSZOWPGU-UHFFFAOYSA-N 1-ethoxy-2,3-difluoro-4-(2-iodoethyl)benzene Chemical compound C(C)OC1=C(C(=C(CCI)C=C1)F)F RAYQDNSSZOWPGU-UHFFFAOYSA-N 0.000 description 2
- DYASUFNACNHJMK-UHFFFAOYSA-N 4-ethoxy-2,3-difluorobenzaldehyde Chemical compound CCOC1=CC=C(C=O)C(F)=C1F DYASUFNACNHJMK-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AVOGLGBKOFOSBN-UHFFFAOYSA-N 1-ethoxy-2,3-difluorobenzene Chemical compound CCOC1=CC=CC(F)=C1F AVOGLGBKOFOSBN-UHFFFAOYSA-N 0.000 description 1
- RBNNHALDGIKSBZ-UHFFFAOYSA-N 2-(2,3-difluorophenyl)ethanol Chemical compound OCCC1=CC=CC(F)=C1F RBNNHALDGIKSBZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- JIZLLTCCAHTZPG-UHFFFAOYSA-N chloromethylbenzene;triphenylphosphane Chemical compound ClCC1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JIZLLTCCAHTZPG-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
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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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
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Abstract
The invention relates to a liquid crystal composition for a VA-LCD (vertical alignment-liquid crystal display) with low threshold, low power consumption, low viscosity and quick response. The composition comprises 5-90% of a compound selected from formula (I) as a first component; 1-75% of a compound selected from formula (II) as a second component; 1-75% of a compound selected from formula (III) as a third component; 1 to 65% of a compound selected from the group consisting of compounds of formula (IV) as a fourth component; 0 to 30% of a compound selected from the group consisting of compounds of formula (V) as a fifth component; 0 to 30 percent of compound selected from formula (VI) as a sixth component; 0 to 20% by weight of a compound selected from the group consisting of compounds of formula (VII) as the seventh component; 0 to 20 percent of compound selected from formulas (VIII a) and (VIII b) is used as an eighth component; 0 to 10% of a compound selected from the group consisting of formula (IXa), (IXa) and (IXa) as the ninth component; 0 to 20% of a compound selected from the group consisting of the compounds of formulae (Xa), (Xa) and (Xa) as a tenth component; 0 to 30% of a compound selected from the group consisting of the compounds of formula (XI a), (XI b) and (XI c) as an eleventh component. The composition can still ensure lower viscosity under the condition of low power consumption.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal composition for a VA-LCD (vertical alignment-liquid crystal display) with low threshold, low power consumption and low viscosity and quick response.
Background
With the development of liquid crystal display technology, liquid crystal display devices are widely used in military, communication, finance, education, research and large-area and small-area electronic devices, such as vehicles and mobile phones. With the trend of the wide viewing angle technology of VA type becoming LCD, VA-LCD is widely used in automobiles, mobile phones, computers and the like, becoming an essential daily necessity for people's life. Therefore, VA-LCDs have also been the subject of research. The arrangement mode of liquid crystal molecules in the VA-LCD box is vertically arranged (vertical array is called VA for short).
However, because the low-threshold products of the VA-LCD cannot be widely applied, the lowest low-threshold voltage is about 1.3V or lower at present, and because the low-threshold products have poor UV resistance and low-temperature stability; the liquid crystal is poured, and then the seal is blackened, and the seal is blackened after UV or high temperature, the viscosity is large, the pouring is slow and other problems are solved, so that the performance requirements of the low-threshold VA-LCD can not be met.
Chinese application 20161074171.5 discloses a liquid crystal composition for VA-LCD with low threshold and low power consumption, which satisfies the requirement of low power consumption, but the viscosity is increased, and the performance requirement of low viscosity and quick response cannot be satisfied.
The present invention has been made in view of this situation.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects of the prior art and provide a liquid crystal composition for VA-LCD with low threshold, low power consumption and low viscosity and quick response, wherein the liquid crystal composition for VA-LCD has the advantages of strong anti-UV capability, good high and low temperature stability, low threshold value of about 1.2V, small viscosity, quick response and no phenomenon of blackening after UV or high temperature; meanwhile, the anti-pollution capacity is better; can fully meet the performance requirement of the low-threshold VA-LCD.
In order to solve the technical problems, the invention adopts the following technical scheme:
a liquid crystal composition for VA-LCD with low threshold value, low power consumption and low viscosity is characterized in that the liquid crystal composition comprises the following components in percentage by weight
Comprises the following steps: 5 to 90% of at least one compound selected from the compounds represented by the formula (I) as a first component;
wherein R is 1 Is C 1 ～C 10 The linear alkyl group of (1); r 1 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is 1 Is 0 or 1; n is 1 Is 1 or 2;
1 to 75% of at least one compound selected from the group represented by the formula (II) as a second component;
wherein R is 10 Is C 1 ～C 10 Straight chain alkyl group of；R 10 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is a unit of 10 Is 0 or 1;
1 to 75% of at least one compound selected from the group represented by the formula (III) as a third component;
wherein R is 11 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (A), (B), (C) and (C), R 11 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is 11 Is 0 or 1;
1 to 65% of at least one compound selected from the group represented by the formula (IV) as a fourth component;
wherein R is 2 Is C 1 ～C 10 Linear alkyl or alkoxy of, R 2 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is 4 Is 0 or 1;
0 to 30% of at least one compound selected from the group consisting of compounds represented by the formula (V) as a fifth component;
wherein R is 3 Is C 1 ～C 10 Linear alkyl or alkoxy groups of (a); r is 3 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is a unit of 3 Is 0 or 1;
0 to 30% of at least one compound selected from the group consisting of compounds represented by the formula (VI) as a sixth component;
wherein R is 4 Is C 1 ～C 10 Linear alkyl or alkoxy of R 4 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1);
0 to 20 percent of one or more compounds selected from the compounds represented by the formula (VII) as a seventh component;
wherein R is 5 Is C 1 ～C 10 Linear alkyl radical of (2), R 5 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1);
is a 1, 4-substituted phenylene group or a trans-1, 4-substituted cyclohexyl group; n is 7 Is 0 or 1;
0 to 20% of at least one compound selected from the group consisting of compounds represented by the formulae (VIII a) and (VIII b) as an eighth component;
wherein R is 6 Is C 1 ～C 10 The linear alkyl group of (1); r is 6 Is a C 1 ～C 10 Is linear alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is 5 Is 0 or 1;
0 to 10% of at least one compound selected from the group consisting of compounds represented by the formulae (IXa, IXb) as the ninth component;
wherein m is 6 、m 7 、m 8 、m 9 Is 0 or 1; r 7 Is C 1 ～C 10 Straight-chain alkyl or alkoxy, R 7 Is C 1 ～C 10 Is a straight chain alkoxy radical of (C) 1 ～C 5 The linear alkyl group of (1);
is a 1, 4-substituted phenylene group or a trans-1, 4-substituted cyclohexyl group;
0 to 20% of at least one compound selected from the group consisting of compounds represented by the formulae (Xa) and (XB) as a tenth component;
wherein R is 8 Is C 1 ～C 10 Straight chain alkyl of (2), R 8 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (a), (b), and (c) 10 Is 0 or 1;
0 to 30% of at least one compound selected from the group consisting of the compounds represented by the formulae (XI a), (XI b) and (XI c) as an eleventh component;
wherein R is 9 Is C 1 ～C 10 The linear alkyl group of (1); r is 9 Is a C 1 ～C 10 Is a straight chain alkoxy radical of (C) 1 ～C 5 The linear alkyl group of (1); m is 2 Is 0 or 1.
The compound constituting the first component of the liquid crystal composition for VA-LCD of the invention has relatively large negative dielectric anisotropy, and the refractive index anisotropy delta n value is relatively moderate. Plays an important role in adjusting both refractive index and dielectric anisotropy. The compounds of the second and the third components of the liquid crystal composition for the VA-LCD have good intersolubility, small refractive index, certain polarity and small viscosity, and play an important role in adjusting the properties of the composition such as threshold value, viscosity and the like. The compounds of the fourth and the fifth components of the liquid crystal composition for the VA-LCD have the characteristics of good intersolubility, wide nematic phase temperature range, moderate refractive index anisotropy, large elastic constant, moderate viscosity and the like. Plays an important role in adjusting the working temperature range, viscosity, elastic constant and other properties of the composition. The compound constituting the sixth component of the liquid crystal composition for VA-LCD of the present invention has relatively large negative dielectric anisotropy, and the refractive index anisotropy delta n value is relatively moderate. Plays an important role in adjusting both refractive index and dielectric anisotropy. The compounds of the seventh and eighth components of the liquid crystal composition for the VA-LCD have the characteristics of high refractive index anisotropy, wide nematic liquid crystal range, high NI transition temperature, moderate viscosity and the like. Plays an important role in adjusting the working temperature range and the refractive index coverage range of the composition. The compound constituting the ninth component of the liquid crystal composition for VA-LCD of the present invention has the characteristics of high NI transition temperature, wide nematic phase temperature range, large viscosity, etc. Plays an important role in adjusting the working temperature range of the composition. The compound constituting the tenth component of the liquid crystal composition for VA-LCD of the invention has the characteristics of low NI transition temperature, very small refractive index anisotropy, small viscosity, good intersolubility, large elastic constant and the like, and plays an important role in adjusting the properties of the composition such as viscosity, elastic constant and the like. The compound which forms the eleventh component of the liquid crystal composition for the VA-LCD has relatively large negative dielectric anisotropy, the refractive index anisotropy delta n value of the compound is relatively moderate, and the compound plays an important role in adjusting two parameters of the refractive index and the dielectric anisotropy. The liquid crystal composition which is composed of the eleven components according to a specific proportion has the advantages of strong anti-UV capability, good high and low temperature stability, small viscosity, low threshold value of about 1.2V, and no black phenomenon after UV or high temperature; meanwhile, the anti-pollution capacity is better; the perfusion is fast; can fully meet the performance requirement of the low-threshold VA-LCD.
The compound constituting the first component of the liquid crystal composition for VA-LCDs of the present invention is described in detail in the patent application having application number 201610231181.8. The following will describe in detail the preparation process of the compound represented by the formula (I-8) as an example, which comprises the steps of:
(1) A1000 ml four-necked flask was charged with 58.5g of 2, 3-difluorophenetole (compound a-1), 42g of potassium tert-butoxide and 500ml of tetrahydrofuran. Under the protection of nitrogen, the temperature is reduced to-90 to-100 ℃, 200ml of 2.5mol/L butyl lithium solution is dripped, and then the temperature is kept for 1.5h. 30g of N, N-dimethylformamide is added dropwise at-90 to-100 ℃. Slowly warm to room temperature and stir for 3h. The feed liquid is poured into hydrochloric acid ice water for hydrolysis, ethyl acetate is used for extraction, drying and silica gel column is used for obtaining 4-ethoxy-2, 3-difluorobenzaldehyde (compound 1-1) with the purity of 97.5 percent (GC) and the yield of 84 percent. The reaction formula is as follows:
(2) A1000 ml four-necked flask was charged with 162g of chlorotoluene triphenylphosphine salt and 500ml of tetrahydrofuran. Under the protection of nitrogen, 58g of potassium tert-butoxide is added at 0 ℃ and then the temperature is kept for 15min. A solution of 80g of 4-ethoxy-2, 3-difluorobenzaldehyde (compound 1-1) and 100ml of tetrahydrofuran was added dropwise at 0 ℃. After the addition, the mixture was stirred at room temperature for 3 hours. After the reaction, water is added into the material liquid to terminate the reaction, petroleum ether is purified, and the product is passed through a silica gel column to obtain 4-ethoxy-2, 3-difluorobenzyl alcohol methyl ether (compound 2-1), the purity is 97.3 percent, and the yield is 85 percent. The reaction formula is as follows:
(3) A1000 ml four-necked flask was charged with the compound 2-1, 73g of 30% hydrochloric acid, 160ml of water, 160ml of tetrahydrofuran, and refluxed for 12 hours. After the reaction was completed, extraction was performed with ethyl acetate, followed by neutralization, drying and passing through a silica gel column to obtain 4-ethoxy-2, 3-difluorophenylacetaldehyde (compound 3-1) with a purity of 84% (GC) and a yield of 70%. The reaction formula is as follows:
(4) 70g of 4-ethoxy-2, 3-difluorophenylacetaldehyde (compound 3-1), 200ml of ethanol and 190ml of water are put into a 1000ml four-mouth bottle, maintained at 0-10 ℃, 18.4g of potassium borohydride is added in batches, and after the addition, the reaction is carried out for 4 hours at room temperature. The feed liquid is poured into diluted hydrochloric acid water for hydrolysis, and then ethyl acetate is extracted. Evaporating to dryness for dissolution, and distilling under reduced pressure to obtain: 4-ethoxy-2, 3-difluorophenethyl alcohol (Compound 4-1). Purity 97.8%, yield 64%. The reaction formula is as follows:
(5) A500 ml four-necked flask was charged with 29g of 2, 3-difluorophenethyl alcohol (Compound No. 4-1), 37g of triphenylphosphine salt, 9.6g of imidazole and 200ml of methylene chloride. 11.8g of elementary iodine is added in batches at 0 ℃, and the reaction is carried out for 6h at room temperature after the addition. After the reaction, water was added to terminate the reaction, and the reaction mixture was washed with water, dried and evaporated to dryness. Silica gel column was passed through petroleum ether to give 4-ethoxy-2, 3-difluorophenethyl iodide (intermediate-1) with a purity of 97.3% (GC) and a yield of 90.3%. The reaction formula is as follows:
(6) A500 ml four-necked flask was charged with 12.7g of trans-pentylcyclohexylcarbonitrile (compound b-1), 8.3g of diisopropylamine, and 100ml of tetrahydrofuran. Under the protection of nitrogen, the temperature is reduced to minus 50 to minus 60 ℃, 32ml2.5mol/L butyl lithium is dripped, and the temperature is kept for 1.5h. Controlling the temperature to be minus 50 ℃ to minus 60 ℃, dropwise adding 20g of 4-ethoxy-2, 3-difluorophenethyl iodide (intermediate-1), and heating to room temperature after dropwise adding, and stirring for 3h. Hydrolyzing with acid water, extracting with ethyl acetate, neutralizing, drying, and evaporating to remove solvent. The negative liquid crystal compound shown in the formula (I-8) is obtained by passing through a silica gel column by using petroleum ether and crystallizing by using ethanol, the purity is 99.5 percent, and the yield is 54 percent. DCS mp62.46 ℃. The reaction formula is as follows:
the compound constituting the first component of the liquid crystal composition for VA-LCD of the present invention can be prepared with reference to the above-mentioned preparation method.
Preferably, the liquid crystal composition for VA-LCD comprises, by weight percent:
5 to 70% of at least one compound selected from the compounds represented by the formula (I) as a first component;
3 to 60% of at least one compound selected from the group represented by the formula (II) as a second component;
3 to 60% of at least one compound selected from the group represented by the formula (III) as a third component;
2 to 55% of at least one compound selected from the group consisting of compounds represented by the formula (IV) as a fourth component;
3 to 27% of at least one compound selected from the group consisting of compounds represented by the formula (V) as a fifth component;
0 to 28% of at least one compound selected from the group consisting of compounds represented by the formula (VI) as a sixth component;
0 to 18 percent of one or more compounds selected from the compounds represented by the formula (VII) as a seventh component;
0 to 15% of at least one compound selected from the group consisting of compounds represented by the formulae (VIII a) and (VIII b) as an eighth component;
0 to 10% of at least one compound selected from the group consisting of compounds represented by the formulae (IXa ) as a ninth component;
0 to 16% of at least one compound selected from the group consisting of compounds represented by the formulae (Xa), and (Xa) as a tenth component;
0 to 28% of at least one compound selected from the group consisting of the compounds represented by the formulae ((XI a), (XI b) and (XI c) as an eleventh component;
preferably, the liquid crystal composition for the VA-LCD comprises, by weight:
10 to 51% of at least one compound selected from the group represented by the formula (I) as a first component;
5 to 51% of at least one compound selected from the group represented by the formula (II) as a second component;
5 to 51% of at least one compound selected from the group represented by the formula (III) as a third component;
5 to 41% of at least one compound selected from the group consisting of compounds represented by the formula (IV) as a fourth component;
5 to 25% of at least one compound selected from the group consisting of compounds represented by the formula (V) as a fifth component;
0 to 26% of at least one compound selected from the group consisting of compounds represented by the formula (VI) as a sixth component;
0 to 15 percent of one or more compounds selected from the compounds represented by the formula (VII) as a seventh component;
0 to 13% of at least one compound selected from the group consisting of compounds represented by the formulae (VIII a) and (VIII b) as an eighth component;
0 to 10% of at least one compound selected from the group consisting of compounds represented by the formulae (IXa ) as a ninth component;
0 to 13% of at least one compound selected from the group consisting of compounds represented by the formulae (Xa), and (Xa) as a tenth component;
0 to 25% of at least one compound selected from the group consisting of the compounds represented by the formulae ((XI a), (XI b) and (XI c) as an eleventh component;
in the formula (I), m 1 Is 0 or 1,n 1 Is 1 or 2; r 1 Is C 1 ～C 7 The linear alkyl group of (1); r is 1 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 A linear alkyl group of (1).
In the formula (II), R 10 Is C 1 ～C 5 Straight chain alkyl of (2), R 10 Is C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
In the formula (III), R 11 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (A), (B), (C) and (C), R 11 Is a C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
In the formula (IV), R 2 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 2 Is C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
In the formula (V), R 3 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 3 Is a C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
In the formula (VI), R 4 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 4 Is a C 1 ～C 5 A linear alkyl or alkoxy group of (2).
The compound of formula (VII) is:
wherein R is 5 Is C 1 ～C 5 Straight chain alkyl of (2), while R 5 ' is-OCH 3 、-OC 2 H 5 -C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 One of them.
The compounds of the formulas (VIII a) and (VIII b) are:
wherein R is 6 Is C 1 ～C 5 Straight chain alkyl of (2), while R 6 ' is-OCH 3 、-OC 2 H 5 -C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 One of them.
The compounds of formula (IXa), (IXa):
wherein R is 7 Is C 1 ～C 5 Linear alkyl or alkoxy of R 7 Is a C 1 ～C 5 A linear alkyl or alkoxy group of (2).
The compounds of formulae (xa), (xb):
wherein R is 8 Is C 1 ～C 5 A linear alkyl group of (1).
After adopting the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the liquid crystal composition for the VA-LCD has the advantages of strong UV resistance, good high and low temperature stability, low threshold value of about 1.2V, low viscosity, quick response and no phenomenon of blackening displayed after UV or high temperature; meanwhile, the anti-pollution capacity is better; the perfusion is fast, and the performance requirements of the low-threshold VA-LCD can be fully met.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the present invention will be described in more detail, clearly and completely with reference to the embodiments, which are used to illustrate the present invention, but the scope of the present invention is not limited to the embodiments. It should be noted that the contents of the respective components in the following examples are "wt%". The abbreviations used in the examples have the following meanings:
NI: nematic phase-Isotropic phase transition temperature (. Degree. C.)
Eta: bulk viscosity (mPa. S) at 20 DEG C
Δ ε:1KHZ, 7-8 μm vertical box test
Δ n: optical anisotropy at 20 ℃ measured at 589nm
V90：fdrive＝128HZ；Bias＝1；Duty＝1；VA Cell gap＝5.0μm；Test Temperature＝23±2℃
Example 1:
the liquid crystal composition has the following performance parameters:
NI：64℃
η101mPa·s
Δε：-12.3
Δn：0.071
V 90 ：1.259
example 2:
the liquid crystal composition has the following performance parameters:
NI：69℃
η：101mPa·s
Δε：-12.3
Δn：0.079
V 90 ：1.21
example 3:
the liquid crystal composition has the following performance parameters:
NI：85
η：67mPa·s
Δε：-9.1
Δn：0.090
V 90 ：1.481
example 4:
the liquid crystal composition has the following performance parameters:
NI：85℃
η：66mPa·s
Δε：-11.4
Δn：0.099
V 90 ：1.466
example 5:
the liquid crystal composition has the following performance parameters:
NI：90℃
η：45mPa·s
Δε：-8.4
Δn：0.072
V 90 ：1.728
example 6:
the liquid crystal composition has the following performance parameters:
NI：77℃
η：91mPa·s
Δε：-11.7
Δn：0.100
V 90 ：1.297
example 7:
the liquid crystal composition has the following performance parameters:
NI：95℃
η：48mPa·s
Δε：-8.7
Δn：0.081
V 90 ：1.712
example 8:
the liquid crystal composition has the following performance parameters:
NI：63℃
η：92Pa·s
Δε：-11.2
Δn：0.07
V 90 ：1.346
example 9:
the liquid crystal composition has the following performance parameters:
NI：77℃
η：89Pa·s
Δε：-10.8
Δn：0.081
V 90 ：1.386
example 10:
the liquid crystal composition has the following performance parameters:
NI：98℃
η：47Pa·s
Δε：-8.7
Δn：0.100
V 90 ：1.765
example 11:
the liquid crystal composition has the following performance parameters:
NI：72℃
η：105Pa·s
Δε：-11.9
Δn：0.089
V 90 ：1.246
example 12:
the liquid crystal composition has the following performance parameters:
NI：85℃
η：71Pa·s
Δε：-10.5
Δn：0.079
V 90 ：1.518
example 13:
the liquid crystal composition has the following performance parameters:
NI：71℃
η：106Pa·s
Δε：-11.9
Δn：0.100
V 90 ：1.202
example 14:
the liquid crystal composition has the following performance parameters:
NI：81℃
η：69Pa·s
Δε：-10.5
Δn：0.069
V 90 ：1.507
comparative example
The power consumption comparison conditions of the new product and the old product are as follows:
the new product formula and parameters are as follows:
the liquid crystal composition has the following performance parameters:
NI：79℃
η：92mPa·s
Δε：-10.7
Δn：0.091
V 90 ：1.371
the old product formula and parameters are as follows:
the liquid crystal composition has the following performance parameters:
NI：79℃ 77
η：90mPa·s 109
Δε：-10.2 -10.1
Δn：0.09 0.099
V 90 ：1.376 1.383
the new and old formula power consumption comparison data are as follows:
from the comparative data: the absolute value of the power consumption of the new formula is smaller than that of the old formula; after UV and high-temperature baking, the power consumption change rate is different by one order of magnitude; it can be seen that the difference in UV resistance between the old and new formulations; the viscosity is basically equivalent, the viscosity of the liquid crystal is increased when the power consumption is reduced in a common situation, but the composition ensures low power consumption, low viscosity and quick response.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (11)
1. A liquid crystal composition for VA-LCD with low threshold value, low power consumption, low viscosity and quick response is characterized by comprising the following components in percentage by weight: 10 to 51% of at least one compound selected from the group represented by the formula (I) as a first component;
wherein R is 1 Is C 1 ～C 10 Linear alkyl radical of (2), R 1 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is a unit of 1 Is 0 or 1; n is 1 Is 1 or 2;
5 to 51% of at least one compound selected from the group represented by the formula (II) as a second component;
wherein R is 10 Is C 1 ～C 10 Linear alkyl radical of (2), R 10 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is 10 Is 0 or 1;
5 to 51% of at least one compound selected from the group represented by the formula (III) as a third component;
wherein R is 11 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (A), (B), (C) and (C), R 11 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is 11 Is 0 or 1;
5 to 41% of at least one compound selected from the group consisting of compounds represented by the formula (IV) as a fourth component;
wherein R is 2 Is C 1 ～C 10 Linear alkyl or alkoxy of, R 2 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Or is an F substituent; m is 4 Is 0 or 1;
5 to 25% of at least one compound selected from the group consisting of compounds represented by the formula (V) as a fifth component;
wherein R is 3 Is C 1 ～C 10 Linear alkyl or alkoxy groups of (a); r is 3 Is a C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is 3 Is 0 or 1;
0 to 26% of at least one compound selected from the group consisting of compounds represented by the formula (VI) as a sixth component;
wherein R is 4 Is C 1 ～C 10 Linear alkyl or alkoxy of, R 4 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1);
0 to 15 percent of one or more compounds selected from the compounds represented by the formula (VII) as a seventh component;
wherein R is 5 Is C 1 ～C 10 Linear alkyl radical of (2), R 5 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 The linear alkyl group of (1);
is a 1, 4-substituted phenylene group or a trans-1, 4-substituted cyclohexyl group; n is 7 Is 0 or 1;
0 to 13% of at least one compound selected from the group consisting of compounds represented by the formulae (VIII a) and (VIII b) as an eighth component;
wherein R is 6 Is C 1 ～C 10 The linear alkyl group of (1); r 6 Is C 1 ～C 10 Is linear alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is 5 Is 0 or 1;
0 to 10% of at least one compound selected from the group consisting of compounds represented by the formulae (IXa, IXb) as the ninth component;
wherein m is 6 、m 7 、m 8 、m 9 Is 0 or 1; r is 7 Is C 1 ～C 10 Straight-chain alkyl or alkoxy, R 7 Is a C 1 ～C 10 Is linear alkoxy or is C 1 ～C 5 The linear alkyl group of (1);
is a 1, 4-substituted phenylene group or a trans-1, 4-substituted cyclohexyl group;
0 to 13% of at least one compound selected from the group consisting of compounds represented by the formulae (Xa) and (XB) as a tenth component;
wherein R is 8 Is C 1 ～C 10 Straight chain alkyl of (2), R 8 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (a), (b), and (c) 10 Is 0 or 1;
0 to 25% of at least one compound selected from the group consisting of the compounds represented by the formulae (XI a), (XI b) and (XI c) as an eleventh component;
wherein R is 9 Is C 1 ～C 10 The linear alkyl group of (1); r is 9 Is a C 1 ～C 10 Is linear alkoxy or is C 1 ～C 5 The linear alkyl group of (1); m is a unit of 2 Is 0 or 1.
2. The liquid crystal composition for VA-LCD of claim 1, wherein in the formula (I), m 1 Is 0 or 1,n 1 Is 1 or 2; r is 1 Is C 1 ～C 7 The linear alkyl group of (1); r 1 Is C 1 ～C 10 Straight-chain alkoxy or is C 1 ～C 5 Linear alkyl group of (1).
3. The liquid crystal composition for VA-LCD of claim 1, wherein in the formula (II), R 10 Is C 1 ～C 5 The linear alkyl group of (1); r 10 Is C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
4. The liquid crystal composition for VA-LCD of claim 1, wherein in the formula (III), R 11 Is CH 2 ＝CH-、CH 2 ＝CH-CH 2 -、CH 3 -CH＝CH-、CH 2 ＝CH-CH 2 -CH 2 One of (A), (B), (C) and (C), R 11 Is C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
5. The liquid crystal composition for VA-LCD of claim 1, wherein in the formula (IV), R is 2 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 2 Is C 1 ～C 5 A linear alkyl or alkoxy group of (2).
6. The liquid crystal composition for VA-LCD according to claim 1, wherein in the formula (V), R 3 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 3 Is a C 1 ～C 5 A linear alkyl or alkoxy group of (2).
7. The liquid crystal composition for VA-LCD according to any one of claims 1 to 6, wherein in the formula (VI), R 4 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 4 Is a C 1 ～C 5 A linear alkyl or alkoxy group of (2).
8. The liquid crystal composition for VA-LCD according to any of claims 1-6, characterized in that said compound of formula (vii) is:
wherein R is 5 Is C 1 ～C 5 Straight chain alkyl of (2), while R 5 ' is-OCH 3 、-OC 2 H 5 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 One of them.
9. The liquid crystal composition for VA-LCD of claim 8, wherein said compounds of formulae (viia), (viib) are:
wherein R is 6 Is C 1 ～C 5 While R is a linear alkyl group of 6 ' is-OCH 3 、-OC 2 H 5 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 One of them.
10. The liquid crystal composition for VA-LCD according to claim 8, wherein said compound of formula (ixa), (ixb) is:
wherein R is 7 Is C 1 ～C 5 Linear alkyl or alkoxy of, R 7 Is C 1 ～C 5 Linear alkyl or alkoxy groups of (a).
11. The liquid crystal composition for VA-LCD according to claim 8, wherein said compounds of formulae (xa), (xb) are:
wherein R is 8 Is C 1 ～C 5 Linear alkyl group of (1).
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| CN111440618B (en) * | 2020-04-24 | 2023-12-26 | 烟台显华化工科技有限公司 | Low-refractive-index low-threshold negative dielectric anisotropy liquid crystal composition and application thereof |
| CN111575022A (en) * | 2020-06-11 | 2020-08-25 | 烟台显华化工科技有限公司 | Negative liquid crystal composition with terminal alkene structure and application thereof |
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