CN110407783B - Benzofuran polymerizable compound and application thereof - Google Patents
Benzofuran polymerizable compound and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
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- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
Abstract
The invention relates to the technical field of liquid crystal materials, in particular to a liquid crystal materialBenzofuran polymerizable compounds and application thereof, wherein the compounds have a structure shown in a general formula I. Compared with the prior art, the compound provided by the invention has the advantages of good solubility, better alignment effect, faster polymerization rate, more complete polymerization and lower residue, so that the problem of poor display is improved to a greater extent. The liquid crystal composition containing the compound has lower viscosity, can realize quick response, and simultaneously has moderate dielectric anisotropy delta £ and the liquid crystal display element or the liquid crystal display containing the liquid crystal composition has the properties of wider nematic phase temperature range, proper or higher birefringence anisotropy delta n, higher resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and relates to a benzofuran polymerizable compound and application thereof.
Background
In recent years, liquid crystal display devices have been widely used in various electronic devices, such as smart phones, tablet computers, car navigators, televisions, and the like. Representative liquid crystal display modes include a Twisted Nematic (TN) mode, a Super Twisted Nematic (STN) mode, an in-plane switching (IPS) mode, a Fringe Field Switching (FFS) mode, and a Vertical Alignment (VA) mode. Among them, the VA mode receives increasing attention because of having a fast fall time, a high contrast ratio, a wide viewing angle, and a high quality image.
However, the liquid crystal medium used for the display element of the active matrix addressing type such as VA mode has its own disadvantages, such as a significantly inferior image sticking level to that of the display element of positive dielectric anisotropy, a relatively slow response time, a relatively high driving voltage, and the like. In order to solve the above problems, some new VA display technologies, such as MVA technology, PVA technology, PSVA technology, have appeared. The PSVA technology not only realizes a wide-viewing-angle display mode similar to MVA/PVA, but also simplifies the CF process, improves the aperture opening ratio while reducing the CF cost, and can obtain higher brightness and further obtain higher contrast. In addition, because the liquid crystal on the whole surface has a pretilt angle, the domino delay phenomenon is avoided, the faster response time can be obtained under the condition of keeping the same driving voltage, and the afterimage level is not influenced.
The prior art has found that the application of LC mixtures and RMs in PSA displays still has some disadvantages. First, not every desired soluble RM is suitable for PSA displays to date: at the same time, if it is desired to carry out the polymerization by means of UV light without adding photoinitiators, which may be advantageous for certain applications, the choice becomes smaller: in addition, the "material system" formed by the combination of the LC mixture (hereinafter also referred to as "LC host mixture") with the selected polymerizable components should have the lowest rotational viscosity and the best opto-electronic properties for increasing the "voltage holding ratio" (VHR) to achieve the effect. In PSVA, high VHR after irradiation with (UV) light is very important, otherwise it leads to problems such as image sticking in the final display. So far, there has been a problem that the polymerizable unit is too short for the UV sensitive wavelength, or no tilt angle or insufficient tilt angle occurs after the light irradiation, or the polymerizable component has poor uniformity after the light irradiation. Not all combinations of LC mixtures and polymerizable components are suitable for PSVA displays.
Therefore, the synthesis of polymerizable compounds having a novel structure and the study of the structure-performance relationship have become important works in the field of liquid crystals.
Disclosure of Invention
It is a first object of the present invention to provide a polymerizable compound useful in polymer stabilization techniques. The liquid crystal composition containing the compound has better alignment effect, more complete polymerization and lower residue. And the compound has low price and stable performance, can be widely applied to the field of liquid crystal display and has important application value.
The liquid crystal compound has the following structure:
wherein, the P1、P2、P3Independently of one another, an acrylate, methacrylate, fluoroacrylate, chloroacrylate, vinyloxy, oxetane or epoxy group; z is1、Z2、Z3Independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-O-, -CH ═ N-, -N ═ CH-, -N ═ N-, -C ═ C-, C1-C12Alkylene or C2-C12Wherein said C is1-C12Alkylene or C2-C12May be independently substituted with F, Cl, or CN, and one or more non-adjacent-CH2The radicals may be replaced, independently of one another, by-O-, -S-, -NH-, -CO-, COO-, -OCO-, -OCOO-, -SCO-, -COS-or an olefinic bond in such a way that they are not linked directly to one another; ring A and ring B independently of each other represent 1, 4-cyclohexylene or 1, 4-phenylene; said L1，L2，L3Independently of one another represent-F, -Cl, -CN, -NO2、-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-CH2CH(CH3)C2H5、-OCH3、-OC2H5、-COCH3、-COC2H5、-COOCH3、-COOC2H5、-CF3、-OCF3、-OCHF2or-OC2F5；r1、r2、r3Represents independently of one another 0, 1, 2 or 3; m represents 0 or 1.
The compounds of the invention, in the general formula I, relate to P1、P2、P3: preferably, P1、P2、P3Independently of one another, a methacrylate group or an acrylate group.
With respect to Z1、Z2、Z3: preferably, Z is1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C8Alkylene or alkoxy of (a); more preferably, Z is1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C6Alkylene or alkoxy groups of (a).
With respect to L1、L2: preferably, said L1，L2Independently of one another represent-F, -Cl, -CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3(ii) a More preferably, L1、L2Independently of one another represent-F, -Cl, -CH3、-OCH3、-C2H5、-OC2H5。
With respect to L3: preferably, L3represents-F, -Cl or-CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3One of (1); more preferably, L3Represents F or Cl.
About r1、r2、r3: preferably, r1、r2、r3Represents independently of one another 0, 1 or 2; more preferably, r3Represents 0 or 1.
The compounds of the invention, preferably in formula I, P1、P2、P3Representing a methacrylate group or an acrylic groupAn ester group;
z is1、Z2、Z3Independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-O-, -CH ═ N-, -N ═ CH-, -N ═ N-, -C ═ C-, C1-C12Alkylene or C2-C12Wherein said C is1-C12Alkylene or C2-C12May be independently substituted with F, Cl, or CN, and one or more non-adjacent-CH2The radicals may be replaced, independently of one another, by-O-, -S-, -NH-, -CO-, COO-, -OCO-, -OCOO-, -SCO-, -COS-or an olefinic bond in such a way that they are not linked directly to one another; ring A and ring B independently of each other represent 1, 4-cyclohexylene or 1, 4-phenylene; said L1，L2，L3Independently of one another represent-F, -Cl, -CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-CH2CH(CH3)C2H5、-OCH3、-OC2H5、-CF3、-OCF3、-OCHF2or-OC2F5；r1、r2、r3Represents independently of one another 0, 1 or 2; m represents 0 or 1.
Further preferably, in formula I, P1、P2、P3Represents a methacrylate group or an acrylate group; z is1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C8Alkylene or alkoxy of (a); ring A and ring B independently of each other represent 1, 4-cyclohexylene or 1, 4-phenylene; l is1、L2、L3represents-F, -Cl or-CH3、-OCH3、-C2H5、-OC2H5；r1、r2、r3Represents independently of one another 0, 1 or 2; m represents 0 or 1.
Even more preferably, in formula I, P1、P2、P3Represents a methacrylate group, an acrylate group; z is1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C6Alkylene or alkoxy of (a); l is1、L2Independently of one another represent-F, -Cl, -CH3、-OCH3、-C2H5、-OC2H5；L3Represents F or Cl; ring A and ring B independently of each other represent 1, 4-cyclohexylene or 1, 4-phenylene; r is1、r2、r3Independently of one another, represents 0, 1 or 2; m represents 0 or 1.
As a still further preferred embodiment of the present invention, in the compound: when m is 0 and ring A is 1, 4-cyclohexylene, L1、L2、L3Independently of one another represents-F or-Cl; or, when m is 1, ring a is 1, 4-cyclohexylene, and ring B is 1, 4-phenylene, r is3Represents 0; or, when m is 1, and ring A and ring B are both 1, 4-cyclohexylene, r1＝r20; or, when r1And/or r2When represents 2, r3Represents 0; or, when L is2represents-CH3、-OCH3、-C2H5、-OC2H5And r is one of2When not 0, r3Represents 0; or, when ring A is 1, 4-phenylene, r1+r2+r3≤4。
As the most preferred embodiment of the present invention, the compound is selected from one of the following compounds:
as the best embodiment of the present invention, the compound is selected from one of the following compounds:
the second object of the present invention is to protect a composition containing the liquid crystal compound. Preferably, the mass percentage of the compound in the composition is 0.01-10%, more preferably 0.01-5%, and even more preferably 0.1-3%.
The third purpose of the invention is to protect the application of the liquid crystal compound and the composition containing the liquid crystal compound in the field of liquid crystal display, preferably in a liquid crystal display device. The liquid crystal display device includes, but is not limited to, TN, ADS, VA, PSVA, FFS or IPS liquid crystal display. The liquid crystal compound or the composition containing the liquid crystal compound has the properties of wide nematic phase temperature range, proper or high birefringence anisotropy delta n, high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the invention, which is intended to include within the scope of the appended claims all such equivalent changes and modifications as may be made without departing from the spirit of the invention disclosed herein.
The liquid crystal compounds used in the following examples can be synthesized by a known method or obtained from a publicly available commercial source, unless otherwise specified, and these synthesis techniques are conventional, and the resulting liquid crystal compounds are tested to meet the standards for electronic compounds.
According to the conventional detection method in the field, various performance parameters of the liquid crystal compound are obtained through linear fitting, wherein the specific meanings of the performance parameters are as follows:
Δ n represents optical anisotropy (25 ℃); Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz); γ 1 represents rotational viscosity (mpa.s, 25 ℃); cp stands for clearing point.
Example 1
The structural formula of the liquid crystal compound is as follows:
the synthetic route for the preparation of compound BYLC-01 is shown below:
the method comprises the following specific steps:
(1) synthesis of Compound BYLC-01-1:
40g of the reaction flask was charged
14.0g of anhydrous potassium carbonate, 200ml of toluene, 150ml of ethanol, 150ml of water, 0.3g of tetratriphenylphosphine palladium, heated under reflux for 8 hours, and subjected to conventional post-treatment to obtain 45.1g of an off-white solid (compound BYLC-01-1), HPLC: 99.7 percent and the yield is 87.1 percent;
(2) synthesis of Compound BYLC-01-2:
45.1g of compound BYLC-01-1, 6g of NaOH and 400ml of deionized water are added into a reaction bottle, and the mixture is stirred for 2 hours at normal temperature. After acidification with hydrochloric acid, conventional work-up was carried out to give a white solid (compound BYLC-01-2), 43.1g, HPLC: 99.8 percent and the yield is 95.8 percent
(3) Synthesis of Compound BYLC-01:
under the protection of nitrogen, 43.1g of compound BYLC-01-2, 28.5g of triethylamine and 200mL of dichloromethane are added into a reaction bottle, the temperature is reduced to-10 ℃, 29.5g of methacryloyl chloride is dropwise added at the temperature of-10-0 ℃, the reaction solution is heated to room temperature to react for 6h, poured into water, neutralized by aqueous solution of uranium bicarbonate, subjected to conventional post-treatment, purified by chromatography, eluted by normal hexane, and recrystallized by ethanol to obtain 36.5g of white solid (compound BYLC-01), LC: 99.8%, yield: 82.4 percent.
The resulting white solid BYLC-01 was analyzed by GC-MS and the M/z of the product was 522.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.55(m,6H),6.65-7.95(m,11H)。
Example 2
The structural formula of the liquid crystal compound is as follows:
the synthetic route for the preparation of compound BYLC-02 is shown below:
the method comprises the following specific steps:
synthesis of Compound BYLC-02:
under the protection of nitrogen, adding 45.0g of compound BYLC-01-2, 32.5g of triethylamine and 250mL of dichloromethane into a reaction bottle, cooling to-10 ℃, controlling the temperature to-10 ℃ -0 ℃, dropwise adding 28.0g of acryloyl chloride, raising the temperature to room temperature, reacting for 6h, pouring the reaction liquid into water, neutralizing with a uranium bicarbonate aqueous solution, carrying out conventional aftertreatment, carrying out chromatographic purification, eluting with n-hexane, and recrystallizing with ethanol to obtain 39.3g of a white solid (compound BYLC-02), wherein LC: 99.8%, yield: 84.5 percent.
The obtained white solid BYLC-02 was analyzed by GC-MS and the M/z of the product was 480.1(M +).
1H-NMR(300MHz,CDCl3):5.15-5.75(m,3H),5.85-6.85(m,8H),7.05-7.95(m,9H)。
Example 3
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-03 was analyzed by GC-MS and the M/z of the product was 558.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,7H),5.35-6.55(m,6H),6.65-7.95(m,11H)。
Example 4
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-04 was analyzed by GC-MS and the M/z of the product was 540.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,6H),6.65-7.95(m,11H)。
Example 5
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
The other conditions were the same as in example 1.
The resulting white solid BYLC-05 was analyzed by GC-MS and the M/z of the product was 540.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,6H),6.65-7.95(m,11H)。
Example 6
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-06 was analyzed by GC-MS and the M/z of the product was 522.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,7H),5.35-6.55(m,8H),6.65-7.95(m,11H)。
Example 7
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
The other conditions were the same as in example 1.
The resulting white solid BYLC-07 was analyzed by GC-MS and the M/z of the product was 536.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,8H),6.65-7.95(m,11H)。
Example 8
The structural formula of the liquid crystal compound is as follows:
the resulting white solid, BYLC-08, was analyzed by GC-MS and the product had an M/z of 582.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.85(m,14H),7.05-7.95(m,7H)。
Example 9
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-09 was analyzed by GC-MS and the M/z of the product was 446.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.85(m,8H),7.05-7.95(m,5H)。
Example 10
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-10 was analyzed by GC-MS and the M/z of the product was 536.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.45(m,12H),5.35-6.85(m,8H),7.05-7.95(m,8H)。
Example 11
The structural formula of the liquid crystal compound is as follows:
to be provided with
Instead of the former
Other reaction conditions were the same as in example 1.
The resulting white solid BYLC-11 was analyzed by GC-MS and the M/z of the product was 552.1(M +).
1H-NMR(300MHz,CDCl3):1.55-2.45(m,12H),5.35-6.85(m,8H),7.05-7.95(m,8H)。
Example 12
According to the technical scheme of the embodiment, the following liquid crystal compounds can be synthesized only by simply replacing corresponding raw materials without changing any substantial operation.
Example 13
The properties of the lc mixture BHR87800 are listed in table 1:
TABLE 1 summary of properties of mixed crystal BHR87800
Wherein mixture BHR87800 was purchased from billions of space-time liquid Crystal technology, Inc. 0.3% of liquid crystal composition BHR87800 containing BYLC-01 to 99.7% of the polymerizable compound provided in example 1 was added thereto and uniformly dissolved to obtain mixture PM-1.
0.3% of the polymerizable compound BYLC-02 provided in example 3 to 99.7% of a liquid crystal composition BHR87800 were added thereto and uniformly dissolved to obtain a mixture PM-2.
0.3% of the polymerizable compound BYLC-03 as provided in example 4 to 99.7% of a liquid crystal composition BHR87800 were added thereto and uniformly dissolved to obtain a mixture PM-3.
0.3% of the polymerizable compound BYLC-05 to 99.7% of BHR87800 (supplied in example 9) was added thereto and uniformly dissolved to obtain a mixture PM-4.
The physical properties of PM-1, PM-2, PM-3, and PM-4 were almost the same as those of the mixture BHR 87800. PM-1, PM-2, PM-3, PM-4 were injected into a test cell with a gap of 4.0 μm and a vertical alignment using a vacuum infusion method. The cell was irradiated with ultraviolet rays using a high-pressure mercury ultraviolet lamp while applying a square wave having a frequency of 60HZ and a driving voltage of 16V to adjust the irradiation intensity of the cell surface to 30mW/cm2 for 600s, to obtain a vertically aligned liquid crystal display element after polymerization, the pretilt angle was measured using an LCT-5016E liquid crystal electrooptical parameter tester, the cell was then disassembled, and the polymerizable compound remaining in the liquid crystal composition was measured using high performance liquid chromatography HPLC, and the results are summarized in tables 2 and 3.
Comparative example
0.3% of a CP polymerizable compound was added to 99.7% of the liquid crystal composition BHR87800, and the mixture was uniformly dissolved to obtain a mixture PM-5. The physical properties of PM-5 were almost not different from those of the above mixture BHR 87800. PM-5 was injected into a test cell with a gap of 4.0 μm and a vertical alignment using a vacuum infusion method. The cell was irradiated with ultraviolet rays using a high-pressure mercury ultraviolet lamp while applying a square wave having a frequency of 60HZ and a driving voltage of 16V to adjust the irradiation intensity of the cell surface to 30mW/cm2 for 600s, to obtain a vertically aligned liquid crystal display element after polymerization, the pretilt angle was measured using an LCT-5016E liquid crystal electrooptical parameter tester, the cell was then disassembled, and the polymerizable compound remaining in the liquid crystal composition was measured using high performance liquid chromatography HPLC, and the results are summarized in tables 2 and 3.
TABLE 2 summary of pretilt angles before and after UV
TABLE 3 summary of polymer residual data
As can be seen from the comparative data in tables 2 and 3, the polymerizable compound of the present invention has better alignment effect, faster polymerization rate, more complete polymerization and lower residue than the polymerizable liquid crystal compound CP, thereby greatly improving the problem of poor display.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (8)
1. A benzofuran polymerizable compound characterized by being selected from the group consisting of:
2. a liquid crystal composition comprising the compound according to claim 1.
3. The composition according to claim 2, wherein the compound is present in the composition in an amount of 0.01 to 10% by mass.
4. The composition according to claim 3, wherein the compound is present in the composition in an amount of 0.01 to 5% by mass.
5. The composition according to claim 4, wherein the compound is present in the composition in an amount of 0.1 to 3% by mass.
6. Use of a compound according to claim 1 and/or a composition according to any one of claims 2 to 5 in the field of liquid crystal displays.
7. Use of a compound according to claim 1 and/or a composition according to any one of claims 2 to 5 in a liquid crystal display device.
8. The use according to claim 7, wherein the liquid crystal display device comprises a TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
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| CN112645910B (en) * | 2019-10-12 | 2023-08-08 | 石家庄诚志永华显示材料有限公司 | Polymerizable compound, liquid crystal composition, liquid crystal display element, and liquid crystal display |
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| CN113493693A (en) * | 2020-04-01 | 2021-10-12 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition containing polymerizable compound and application thereof |
| CN114989120B (en) * | 2022-06-14 | 2024-03-29 | 陕西师范大学 | Benzofuran luminescent liquid crystal compound and synthetic method and application thereof |
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