CN109749755B - Liquid crystal compound and composition for improving environmental adaptability of liquid crystal material - Google Patents
Liquid crystal compound and composition for improving environmental adaptability of liquid crystal material Download PDFInfo
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Abstract
The invention discloses a nematic liquid crystal composition, which is characterized by comprising one or more compounds with a structural general formula (1):
wherein R is linear alkyl, alkenyl or alkoxy with the carbon number of 1-9; x1～X4Is a methyl group, a chlorine atom, a fluorine atom or a hydrogen atom, and wherein X1～X4At least one is a methyl group or a chlorine atom. The invention has the characteristics of high environmental adaptability and wide liquid crystal phase region, and is suitable for TFT liquid crystal display, in particular to liquid crystal display modes of TN, IPS, FFS, OCB, blue phase and the like.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal compound and a composition for improving the environmental adaptability of a liquid crystal material.
Background
The liquid crystal display has the advantages of flat panel, low power consumption, light weight, no radiation and the like, and is rapidly developed in the field of information display. The liquid crystal display uses the characteristics of optical anisotropy and dielectric anisotropy of a liquid crystal material to realize a display function. The display modes are classified into Twisted Nematic (TN), Super Twisted Nematic (STN), dynamic scattering mode (DSP), thin film transistor driving mode (TFT), and the like. The TFT liquid crystal display can realize full color, high resolution, wide viewing angle, fast response, etc., has been widely used, and is the most important display technology in the current market.
The liquid crystal material used for liquid crystal display has nematic phase within the temperature range of the use environment, generally-20 ℃ to +70 ℃; meanwhile, the liquid crystal material must have high chemical stability, low viscosity, and suitable application of liquid crystal physical properties such as birefringence, dielectric anisotropy, resistivity and the like. One liquid crystal compound cannot meet all use conditions, and several or even more than ten liquid crystal compounds are compounded to form a mixed liquid crystal material, so that the practical use requirements of a display device can be met.
The liquid crystal material used by the TFT liquid crystal display technology needs to have high resistivity and high voltage holding ratio, and the liquid crystal compound containing fluorine atom substitution can meet the requirements, so that the liquid crystal material is widely applied to TFT liquid crystal. In order to further reduce the driving voltage and shorten the response time, a liquid crystal material having a large dielectric anisotropy and a low rotational viscosity is required. In addition, there is a need for liquid crystal materials that have a high degree of stability, especially when exposed to sunlight or backlight for extended periods of time.
In order to improve the light stability of the liquid crystal material, patent US2008128653 discloses a tetrabiphenyl liquid crystal compound having the structural formula shown as follows, which improves the light stability of the liquid crystal composition:
however, the fluorine-containing quaterphenyl liquid crystal compound has a high melting point, so that the fluorine-containing quaterphenyl liquid crystal compound has low solubility in mixed liquid crystal and is easy to generate crystallization phenomenon at low temperature.
Disclosure of Invention
In view of the demand of liquid crystal display technology for liquid crystal compositions, the present invention aims to provide a tetrakisbiphenyl liquid crystal compound which improves the environmental adaptability of liquid crystal materials and improves the low-temperature compatibility, and a liquid crystal composition which has a wider liquid crystal phase region and high environmental adaptability.
In order to realize the task, the invention adopts the following technical solution:
a tetrabiphenyl liquid crystal compound is characterized in that the structure is shown as the general formula (1):
wherein R is a linear alkyl group, an alkenyl group or an alkoxy group with 1-9 carbon atoms; l is1～L4Is a methyl group, a chlorine atom, a fluorine atom or a hydrogen atom, and L1～L4At least one of which is a methyl group or a chlorine atom.
A liquid crystal composition is characterized in that a first component has a structural general formula shown as (1), and the mass ratio of the first component is 0.5-30%.
The liquid crystal compounds of formula (1) in the compositions of the invention are preferably selected from the following structures:
wherein R is preferably a C1-7 linear alkyl group.
The proportion of the first component of the composition of the invention is between 0.5% and 30% by weight, preferably between 1% and 20% by weight, more preferably between 2% and 15% by weight.
The composition of the present invention comprises at least one liquid crystal compound selected from the group consisting of liquid crystal compounds represented by the general structural formula (2) as a second component:
wherein R is1，R2F, Cl, wherein ring A, ring B and ring C are benzene rings or cyclohexane, the benzene rings can be substituted by 1 or more fluorine atoms, and n is 0, 1. The proportion of the second component of the invention is 0-80%, preferably 10-75%, more preferably 20-70% wt.
Wherein the preferred specific structure of formula (2) is as follows:
wherein (2) -1 is more preferably of the structure:
among them, (2) -2 are more preferably the following specific compounds:
among them, (2) -3 are more preferably the following specific compounds:
among them, (2) to 4 are more preferably the following specific compounds:
among them, (2) to 5 are more preferably the following specific compounds:
the liquid crystal composition of the present invention comprises at least one liquid crystal compound selected from the group consisting of liquid crystal compounds represented by the general structural formula (3) as a third component:
wherein R is a straight-chain alkyl group, an alkenyl group, or an alkyl group containing an ethylenic bond, and ring A, ring B, ring C are a benzene ring or cyclohexane, wherein the benzene ring may be substituted with 1 or more fluorine atoms; x1，X2＝H，F；Y＝F，Cl，OCF3，OCF2H, straight-chain alkyl groups or alkyl groups containing an ethylenic bond, etc.; z ═ CF2O，CH2CH2COO, single bond, etc.; n is 0, 1. The proportion of the third component of the invention is 0-50%, preferably 5-45% by weight, more preferably 10-40%. Wherein the general formula (3) is preferably of the following specific structure:
among them, 3- (1) is preferably a compound:
among them, 3- (2) is preferably a compound:
among them, 3- (3) is preferably a compound:
among them, 3- (4) is preferably a compound:
among them, 3- (5) are preferred compounds:
among them, 3- (6) is preferably a compound:
among them, 3- (7) is preferably a compound:
among them, 3- (8) is preferably a compound:
among them, 3- (9) is preferably a compound:
among them, 3- (10) are preferred compounds:
among them, 3- (11) is preferably a compound:
among them, 3- (12) is preferably a compound:
among them, 3- (13) is preferably a compound:
among them, 3- (14) are preferred compounds:
among them, 3- (15) is preferably a compound:
among them, 3- (16) is preferably a compound:
the liquid crystal composition can also comprise one or more chiral additives, and the content is 0.01-1%; preferably 0.1% to 0.5%. The chiral additive is preferably selected from the following structures:
the liquid crystal composition also comprises a plurality of hindered phenols as antioxidant stabilizers, and the content of the hindered phenols is 1ppm to 10000 ppm; preferably from 10ppm to 1000 ppm. The antioxidant stabilizer is preferably selected from the following structures:
the liquid crystal composition also comprises one or more light stabilizers with the content of 1ppm to 10000 ppm; preferably from 10ppm to 1000 ppm. The light stabilizer is preferably selected from the following structures:
the invention may further comprise one or more liquid crystal components having a polymerizable group in an amount of 1ppm to 10000 ppm; preferably 100ppm to 1000 ppm. The polymerizable liquid crystal component is preferably selected from the following structures:
the invention has the advantages that: the tetrabiphenyl liquid crystal compound has a conjugated tetrabiphenyl structure, has high ultraviolet absorption capacity, and can improve the light stability of a liquid crystal material; methyl or chlorine atoms with larger volume are introduced as lateral substituent groups, so that the acting force between rigid ring molecules of the quaterphenyl is weakened, the melting point is greatly reduced compared with that of the known quaterphenyl liquid crystal compound, and the solubility in mixed liquid crystal is remarkably improved; meanwhile, the compound also has the advantages of higher birefringence and larger dielectric constant. The liquid crystal composition has higher light stability, larger dielectric anisotropy and higher response speed, and is suitable for TFT liquid crystal display technology, especially display modes such as TN, IPS, FFS and the like.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
The preparation method of the liquid crystal formula comprises the following steps: a thermal dissolution method is used. Firstly, weighing monomer liquid crystals with different weight proportions by using a precision balance, heating to 60-100 ℃, and stirring and mixing for 1-2 hours to uniformly dissolve all components. Cooling, filtering, degassing the filtered liquid in high vacuum (less than or equal to 100Pa), and packaging with high-purity nitrogen to obtain the target mixed liquid crystal.
Unless otherwise specified, the liquid crystal compositions according to the invention are prepared according to this process.
And testing the physical property and the photoelectric property of the mixed liquid crystal. The detailed test method of the physical property and the photoelectric property comprises the following steps:
(1) clearing point (Tni):
the polarizing hot stage method: the liquid crystal sample was coated on a glass slide and placed in an orthogonal polarization microscope hot stage with a temperature rise rate of 2 ℃/min. And observing the temperature at which the liquid crystal sample turns black from a bright state in a polarizing microscope, namely the clearing point.
Or by differential scanning calorimetry: the temperature rise rate was set at 2 ℃/min under nitrogen atmosphere.
(2) Low temperature storage temperature (LTS): about 1mL of the mixed liquid crystal was put in a transparent glass bottle and placed in a low-temperature refrigerator. The temperature was set at-20 deg.C, -30 deg.C, -40 deg.C, and stored for 10 days, respectively, and whether there was crystal precipitation or smectic phase was observed. If no crystal is precipitated at the temperature of minus 30 ℃, LTS is less than or equal to minus 30 ℃.
(3) Birefringence (Δ n): respectively measuring ordinary rays (n) by using Abbe refractometer at constant temperature of 25 DEG Co) And extraordinary ray (n)e) Refractive index of (1), birefringence (Δ n) being equal to ne－no。
(4) Dielectric constant (Δ ∈): and (3) testing by using an LCR (liquid crystal resistance) meter at the constant temperature of 25 ℃. Δ ε ═ ε∥-ε⊥I.e. the dielectric constant (. epsilon.) in the direction of the molecular long axis∥) Dielectric constant (. epsilon.) with respect to the minor axis of the molecule⊥) The difference of (a).
(5) Spring constant (K)11，K33): under the constant temperature condition of 25 ℃, K is obtained by testing a liquid crystal capacitance-voltage (C-V) curve and fitting11And K33。
(6) Rotational viscosity (. gamma.)1): under the constant temperature condition of 25 ℃, the transient current value Ip of the liquid crystal molecules deflected along with the movement of the electric field is tested by applying voltage to the liquid crystal test box, and the rotational viscosity gamma is calculated1。
Code number and description:
(1) physical parameters
| (Code) | Description of the invention | Unit of |
| Tni | Clearing points | ℃ |
| TCN | Low temperature storage temperature | ℃ |
| Δε | Dielectric anisotropy constant | |
| Δn | Double refractive index | |
| γ1 | Rotational viscosity | mPa·s |
| K11 | Elasticity constant of splay | pN |
| K33 | Flexural elastic constant | pN |
(2) Structural abbreviations
For example:
example 1:
3, 4, 5-trifluoro-2 "-methyl-4" '-pentyl-1, 1': 4',1": synthesis of 4', 1' -quaterphenyl
The concrete structure is as follows:
the preparation process comprises the following steps:
step 1: synthesis of 4-bromo-3-methyl-4 '-pentyl-1, 1' -biphenyl
Under nitrogen protection, 4-pentylphenylboronic acid (38.4g, 0.2mol), 2-bromo-5-iodotoluene (59.4g, 0.2mol), anhydrous potassium carbonate (82.8g, 0.6mol), tetrabutylammonium bromide (6.4g, 0.02mol), toluene (200mL), ethanol (200mL), water (200mL) were sequentially added to a 1L three-necked round bottom flask equipped with mechanical stirring, a reflux condenser, a thermometer, and a nitrogen gas-guide tube, and bis (triphenylphosphine) palladium dichloride (2.1g, 3mmol) was finally added and replaced with nitrogen gas three times. And starting heating, raising the temperature of the system to 60 ℃ in the system, keeping the temperature and reacting for 4-6 h, and stopping the reaction. Cooling to room temperature, standing for layering, extracting the water phase with toluene, mixing to obtain an organic phase, washing with water to neutrality, drying with anhydrous magnesium sulfate, vacuum filtering, and spin drying to obtain a reddish brown oily liquid. The crude product was distilled under high vacuum to give 35g of a colorless oily liquid product, GC content 96.6%, yield 55.2%.
Step 2: 3, 4, 5-trifluoro-2 "-methyl-4" '-pentyl-1, 1': 4',1": synthesis of 4', 1' -quaterphenyl
Under the protection of nitrogen, 4-bromo-3-methyl-4 '-pentyl-1, 1' -biphenyl (10g, 0.03mol), 3, 4, 5-trifluorobiphenyl boric acid (7.6g, 0.03mol), anhydrous potassium carbonate (12.4g, 0.09mol), tetrabutyl ammonium bromide (0.97g, 0.003mol), toluene (60mL), ethanol (60mL), and water (60mL) are sequentially added into a 250mL single-neck round-bottom flask, and bis (triphenylphosphine) palladium dichloride (0.32g, 0.45mmol) is finally added, nitrogen is replaced for three times, heating is started, reflux reaction is carried out for 5 hours, and the reaction is stopped. Cooling to room temperature, standing for layering, extracting the water phase with toluene, mixing to obtain an organic phase, washing with water to neutrality, drying with anhydrous magnesium sulfate, vacuum filtering, and spin drying to obtain a crude product. The crude product was eluted with V (n-heptane)/V (toluene) 10/1 column chromatography, the eluent was collected, the dried solvent was concentrated, and recrystallization from n-heptane gave 5.8g of a white crystalline product with a GC content of 99.8% and a yield of 43.5%.
Structure identification data:1H NMR(δ，CDCl3)：7.577～7.552(m，4H)，7.522(s，1H)，7.501～7.482(m，1H)，7.470～7.454(m，2H)，7.329～7.313(d，1H，J＝8Hz)，7.285～7.245(m，4H)，2.679～2.647(t，2H，J＝8Hz)，2.382(s，3H)，1.705～1.645(m，2H)，1.396～1.341(m，4H)，0.935～0.908(t，3H，J＝7Hz)；MS(70eV)m/z(％)：444.5(M+，71.06)，387.4(100)，371.3(8.44)。
the above structural identification data indicate that the synthesized compound is indeed compound 3, 4, 5-trifluoro-2 "-methyl-4" '-pentyl-1, 1': 4',1": 4 ", 1"' -quaterphenyl.
The phase transition temperature of the compound is measured by DSC at the condition of temperature rise of 5 ℃/min, and the result is as follows: C82.78N 128.52I.
Example 2:
2 "-chloro-3, 4, 5-trifluoro-4" '-propyl-1, 1': 4',1": synthesis of 4', 1' -quaterphenyl
The concrete structure is as follows:
the preparation process comprises the following steps:
(1) synthesis of 4-bromo-3-chloro-4 '-propyl-1, 1' -biphenyl
Under the protection of nitrogen, 4-propylphenylboronic acid (27.9g, 0.17mol), 3-chloro-4-bromoiodobenzene (54g, 0.17mol), anhydrous potassium carbonate (70.4g, 0.51mol), tetrabutylammonium bromide (5.5g, 0.017mol), toluene (180mL), ethanol (180mL), water (180mL) were sequentially added to a 1L three-necked round bottom flask equipped with a mechanical stirrer, a reflux condenser, a thermometer, and a nitrogen gas-guide tube, and bis (triphenylphosphine) palladium dichloride (1.2g, 1.7mmol) was finally added and replaced with nitrogen gas three times. And starting heating, carrying out reflux reaction for 4-6 h, and stopping the reaction. Cooling to room temperature, standing for layering, extracting the water phase with toluene, mixing to obtain an organic phase, washing with water to neutrality, drying with anhydrous magnesium sulfate, vacuum filtering, and spin drying to obtain a crude product. Dissolving the crude product with n-heptane, passing through silica gel column, eluting with n-heptane, collecting eluate, spin drying, and recrystallizing with ethanol to obtain light orange solid product 43g, with GC content of 97.4% and yield of 81.7%.
(2) Synthesis of (3-chloro-4 '-propyl- [1,1' -biphenyl ] -4-yl) boronic acid
Under the protection of nitrogen, adding 4-bromo-3-chloro-4 '-propyl-1, 1' -biphenyl (43g, 0.139mol) and dried THF (150mL) into a 500mL three-neck round-bottom flask provided with a mechanical stirrer, a thermometer, a constant pressure dropping funnel and a nitrogen gas guide tube, stirring and dissolving completely, cooling to-78 ℃ by using liquid nitrogen, starting to dropwise add n-butyl lithium (0.167mol, 70mL, 2.4M n-hexane solution), reacting for 1h while keeping the temperature after dropwise adding, dropwise adding a THF (50mL) solution of triisopropyl borate (31.4g, 0.167mol) which is frozen in advance, reacting for 1h while keeping the temperature after dropwise adding, naturally returning the temperature, adding a 10% diluted hydrochloric acid solution into the reaction system, stirring for 0.5h, standing and separating, separating out an organic phase, washing to be neutral by water, concentrating under reduced pressure to dryness, recrystallizing by using petroleum ether to obtain 29.3g of a white crystal product, the yield thereof was found to be 76.8%.
(3)2 "-chloro-3, 4, 5-trifluoro-4" '-propyl-1, 1': 4',1": synthesis of 4', 1' -quaterphenyl
Under the protection of nitrogen, sequentially adding (3-chloro-4 '-propyl- [1,1' -biphenyl) into a 250mL single-neck round-bottom flask]-4-yl) boronic acid (3.5g, 0.0126mol), 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl (3.44g, 0.012mol), anhydrous potassium carbonate (5g, 0.036mol), tetrabutylammonium bromide (0.39g, 1.2mmol), toluene (35mL), ethanol (35mL), water (35mL), and finally bis (triphenylphosphine) palladium dichloride (0.13g, 0.18mmol) was added and replaced with nitrogen three times. Heating is started, reflux reaction is carried out for 6 hours, and heating is stopped. Cooling to room temperature, standing for layering, extracting the water phase with toluene, mixing to obtain an organic phase, washing with water to neutrality, drying with anhydrous magnesium sulfate, vacuum filtering, and spin drying to obtain a crude product. Crude product is V(n-heptane)/V(toluene)5/1, and the eluent is collected, dried by spinning, and recrystallized by a mixed solvent of toluene and ethanol to obtain 3g of white crystal product, the GC content is 99.6 percent, and the yield is 57.2 percent.
Structure identification data:1H NMR(δ，CDCl3)：7.723～7.720(m，1H)，7.583～7.530(m，7H)，7.426～7.410(d，1H，J＝8Hz)，7.293～7.239(m，4H)，2.664～2.633(t，2H，J＝7.5Hz)，1.732～1.657(m，2H)，0.999～0.970(t，3H，J＝7.5Hz)。
MS(70eV)m/z(％)：438.2(28.8)，437.3(24.61)，436.2(M+，78.93)，409.2(34.45)，408.2(26.87)，407.2(100)，371.2(13.52)，203.5(36.14)。
the above structural identification data indicates that the synthesized compound is indeed the compound 2 "-chloro-3, 4, 5-trifluoro-4" '-propyl-1, 1': 4',1": 4 ", 1"' -quaterphenyl. The phase transition temperature of the compound is measured by DSC at the temperature rise of 5 ℃/min, and the result is as follows: C99.24N 126.62I.
Example 3:
2 "-chloro-2 ', 3, 4, 5-tetrafluoro-4" ' -propyl-1, 1 ': 4',1": synthesis of 4', 1' -quaterphenyl
The concrete structure is as follows:
the target compound 2 "-chloro-2 ', 3, 4, 5-tetrafluoro-4'" -propyl-1 can be synthesized in the same manner using 4-bromo-2, 3', 4', 5 '-tetrafluoro-1, 1' -biphenyl instead of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl in step (3) of example 1,
1': 4',1": 4', 1' -quaterphenyl.
Structure identification data:1H NMR(δ，CDCl3)：7.726～7.723(m，1H)，7.568～7.528(m，3H)，7.467～7.403(m，2H)，7.375～7.324(m，2H)，7.297～7.241(m，4H)，2.666～2.635(t，2H，J＝7.5Hz)，1.733～1.658(m，2H)，0.999～0.970(t，3H，J＝7Hz)。
MS(70eV)m/z(％)：456.2(26.9)，455.3(22.65)，454.3(M+，75.14)，427.2(35.83)，426.2(28.87)，425.2(100)，389.2(15.31)，212.6(43.45)。
the above structural identification data indicate that the synthesized compound is indeed the compound 2 "-chloro-2 ', 3, 4, 5-tetrafluoro-4" ' -propyl-1, 1 ': 4',1": 4', 1' -quaterphenyl.
The phase transition temperature of the compound is measured by DSC at the condition of temperature rise of 5 ℃/min, and the result is as follows: C90.62N 101.83I.
Composition example 1:
composition example 2:
composition example 3:
composition example 4:
the composition in the above embodiment has large dielectric anisotropy, extremely low rotational viscosity and high stability, and is suitable for display applications such as TN type, IPS type and FFS.
Comparative example 1:
patent US2008128653 discloses tetrabiphenyls liquid crystal compounds having the structural formula shown below:
the liquid crystal phase transition temperature and solubility of the compounds are compared with the compounds of the invention as shown in the following table:
the solubility test comprises adding each compound into the basic formula at a certain ratio, standing at room temperature for 120hr, and observing whether crystal precipitation occurs. The basic formula consists of three monomer liquid crystals (2CCGF, 3CCGF and 5CCGF) in the mass ratio of 2 CCGF: 3 CCGF: 5CCGF is 1: 1: 1.
as can be seen from the table, not only was the melting point of the tetrabiphenyl compound in the comparative example 111 ℃ reached, but a broader smectic phase existed; the melting points of the quaterphenyl compounds are all lower than 100 ℃, and only a nematic phase is shown; solubility tests show that the solubility of the compounds of the invention is greatly improved.
Comparative example 2:
the same monomer composition as in composition example 1, but in which the tetrabiphenyl compound 3PP of the invention is not contained1PUF and 5PP1PUF。
The liquid crystal compositions of comparative example 2 and composition example 1 were respectively poured into TN test cells having a cell thickness of 5 μm and irradiated with 365nm ultraviolet light (energy density of 100 mw/cm)2) The Voltage Holding Ratio (VHR) was tested after 60min irradiation, and the results are given in the following table:
| composition comprising a fatty acid ester and a fatty acid ester | VHR(60℃,16.67ms) |
| Composition example 1 | 97.1％ |
| Comparative example 2 | 95.7％ |
As can be seen from the table, the composition added with the quaterphenyl liquid crystal compound has a higher VHR value, which shows that the compound has a remarkable effect of improving the light stability.
Claims (3)
1. A liquid crystal compound is structurally characterized by having a general formula as follows:
wherein R is a C1-C9 linear alkyl group, an alkoxy group, a C2-C9 alkenyl group; x1～X4Is chlorine, fluorine or hydrogen, and wherein X1～X4At least one is a chlorine atom.
2. A nematic phase liquid crystal composition is characterized by comprising a liquid crystal compound as a first component, wherein the liquid crystal compound is represented by the general structural formula (1), and the mass ratio of the liquid crystal compound to the first component is 0.5-30%:
wherein R is a linear alkyl group, an alkoxy group or an alkenyl group having 1-9 carbon atoms; x1～X4Is chlorine, fluorine or hydrogen, and wherein X1～X4At least one is a chlorine atom.
3. A liquid crystal display element comprising the compound according to claim 1 or the liquid crystal composition according to claim 2.
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