CN109593040B - Polymerizable compound containing propenyl tetrapolymerized group and composition comprising the same - Google Patents
Polymerizable compound containing propenyl tetrapolymerized group and composition comprising the same Download PDFInfo
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Abstract
A polymerizable compound is represented by formula I:
wherein Q represents
P 1 、P 2 Each independently represent
Or
And a liquid crystal composition and a liquid crystal display device containing the polymerizable compound of formula I.
Description
Technical Field
The invention relates to the field of liquid crystal display, in particular to a polymerizable liquid crystal compound containing an allyl tetrapolymerized group, a liquid crystal composition containing the liquid crystal compound, and a display element or a liquid crystal display containing the liquid crystal composition.
Background
Thin film transistor-liquid crystal displays (TFT-LCDs) undergo a long basic research phase, and have become mainstream products in LCD applications due to their advantages of lightness, thinness, environmental protection, high performance, and the like after large-scale production and commercialization: the TFT-LCD can be widely applied to small-sized mobile phone screens, large-sized Notebook computers (Notebook PCs) or monitors (monitors), and large-sized liquid crystal televisions (LCD-TVs).
Early commercial TFT-LCD products basically adopted the TN display mode, and the biggest problem thereof was the narrow viewing angle. With the increase of product size, especially the application in TV field, IPS display mode and VA display mode with wide viewing angle feature are developed and applied in sequence, especially based on the improvement of VA display mode, they have been developed in a breakthrough in each company, which mainly depends on the advantages of VA mode itself, such as wide viewing angle, high contrast, no need of rubbing alignment, etc., and what is more, the dependency of the contrast of VA mode display on the optical anisotropy (Δ n) of liquid crystal, the thickness (d) of liquid crystal cell and the wavelength (λ) of incident light is small, which makes this mode of VA a display technology with great prospect.
However, the liquid crystal medium used for the display element of the active matrix addressing method such as VA mode is not perfect, and for example, the residual image level is significantly inferior to that of the display element of positive dielectric anisotropy, and the liquid crystal medium has disadvantages of relatively slow response time, relatively high driving voltage, and the like. At this time, some novel VA display technologies are still living: the PSVA technology realizes a wide-field-angle display mode similar to MVA/PVA, and simplifies the CF process, thereby reducing the CF cost, improving the aperture opening ratio, obtaining higher brightness and further obtaining higher contrast. In addition, because the liquid crystal of the whole surface has the pretilt angle and does not have domino delay phenomenon, the liquid crystal can obtain faster response time under the condition of keeping the same driving voltage, and the afterimage level can not be influenced. Like UVVA technique, on the basis of keeping PSVA technical advantage, because do not have Slit structure on TFT side, the uneven problem of display that the uneven pixel electrode width arouses has still been improved. Despite the continuous development of display devices, there is a continuing effort to develop new liquid-crystalline compounds which lead to a continuous development of liquid-crystalline media and their properties for use in display devices.
Polymerizable mesogenic units (RMs) are currently very popular and important issues in the display industry, and the possible applications include Polymer Sustained Alignment (PSA) liquid crystal display, polymer sustained blue phase (PS-BP) liquid crystal display, patterned Retarder Film (Pattern Retarder Film), and the like.
The PSA principle is being applied in different typical LC displays, such as PSA-VA, PSA-OCB, PS-IPS/FFS and PS-TN liquid crystal displays. Taking the PSA-VA display, which is currently most widely used, as an example, the pretilt angle of the liquid crystal cell can be obtained by the PSA method, which has a positive effect on the response time. For PSA-VA displays, standard MVA or PVA pixel and electrode designs can be used, but if the electrode design on one side is specially patterned and the other side is not raised, the production can be significantly simplified, while achieving very good contrast and very high light transmission of the display.
The prior art has found that the use of LC mixtures and RMs in PSA displays still has some disadvantages. First, not every soluble RM desired so far is suitable for use in PSA displays; at the same time, if one wishes to carry out polymerization by means of UV light without the addition of photoinitiators, which may be advantageous for certain applications, the choice becomes smaller; in addition, the LC mixture (also referred to below as "LC host mixture") in combination with the selected polymerisable components should form a "material system" having the lowest rotational viscosity and the best optoelectronic properties for increasing the "voltage holding ratio" (VHR) for effectiveness. In PSA-VA, high VHR after irradiation with (UV) light is very important, otherwise it leads to problems such as image sticking in the final display. Not all combinations of LC mixtures and polymerisable components are suitable for PSA displays to date. This is mainly due to the effect of polymerizable units being too short for UV sensitive wavelengths, or no or insufficient tilt angle after illumination, or the poor uniformity of the polymerizable components after illumination, or because the VHR after UV is low for TFT display applications, etc.
Disclosure of Invention
The invention provides a polymerizable compound containing a propylene-based tetrapolymerized group, a negative liquid crystal composition containing the compound, a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition, a PSVA liquid crystal composition especially suitable for display or TV application, and an IPS-mode PSA-IPS liquid crystal composition, wherein especially the polymerizable compound has higher polymerization speed and low residue.
The liquid crystal composition has low viscosity, can realize quick response, and simultaneously has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n (0.09-0.11) and high stability to heat and light. The liquid crystal display element or the liquid crystal display containing the liquid crystal composition has the advantages of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
In order to achieve the above-mentioned advantageous technical effects, the present invention provides a polymerizable compound represented by formula i:
wherein Q represents
P 1 、P 2 Each independently represent
The invention also provides a liquid crystal composition comprising one or more compounds of formula I, one or more compounds of formula II and one or more compounds of formula III,
wherein Q represents
P 1 、P 2 Each independently represent
R 1 、R 2 、R 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more unconnected CH of the indicated groups 2 May be substituted with cyclopentyl, cyclobutyl or cyclopropyl;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-；
m represents 1,2;
n represents 0,1,2.
The one or more compounds shown in the formula I are preferably one or more compounds shown in formulas I-1 to I-2; the one or more compounds shown in the formula II are preferably one or two compounds of the compounds shown in the formulas II-1 to II-14; the one or more compounds of formula III are preferably one or more compounds of formulae III-1 to III-11,
wherein R is 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more unconnected CH of the indicated groups 2 May be substituted with cyclopentyl, cyclobutyl or cyclopropyl.
In these displays using these liquid-crystal compositions, the compounds of the formula I are added to the LC medium and, after incorporation into the LC cell, the pretilt of the liquid-crystal molecules can be formed by UV photopolymerization or crosslinking under application of a voltage between the electrodes. This is advantageous for simplifying the LCD manufacturing process, increasing the response speed, and reducing the threshold voltage.
The compound shown in the formula I has the advantages of good intersolubility with other monomers, good ultraviolet ray tolerance and the like. The Reactive Mesogen (RM) has the advantages of good intersolubility, high charge retention rate (VHR), high polymerization activity (little monomer residue) and the like, and is very suitable for being used as RM in liquid crystal mixtures of PSA (polymer-supported alignment) and PS (polymer-stabilized) modes, especially in the cases of PSA-VA and PSA-IPS.
In addition, any one of the following products containing the compound shown in the formula I also belongs to the protection scope of the invention:
1) A liquid crystal composition;
2) An optically anisotropic body of a liquid crystal composition;
the polymerizable compound of the formula I may have slightly different solubility in liquid crystal depending on the substituent, but may be added in an amount of 1% by mass or more.
The amount (mass ratio) of the polymerizable compound of the formula I added to the liquid crystal composition is preferably 0.01 to 1%, more preferably 0.03 to 0.2%.
The amount (mass ratio) of the compound represented by the formula II added to the liquid crystal composition is preferably 15 to 60%, more preferably 20 to 40%.
The amount (mass ratio) of the compound represented by the formula III added to the liquid crystal composition is preferably 20 to 60%, and more preferably 30 to 50%.
The liquid crystal composition can be a negative liquid crystal composition and can also comprise one or more compounds shown as a formula IV
Wherein R is 5 、R 6 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms a fluorine-substituted alkenyl group having 2 to 10 carbon atoms,An alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more CH in the group shown 2 May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;
w represents O, S or-CH 2 O-。
The compound of formula iv is preferably:
R 61 each independently represents an alkyl group having 2 to 6 carbon atoms.
The liquid crystal composition can also comprise one or more compounds shown as a formula V
Wherein R is 7 、R 8 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
The compound of formula v is preferably:
wherein R is 71 、R 81 Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms;
R 82 represents an alkoxy group having 1 to 5 carbon atoms;
R 71 、R 81 more preferably, it is a vinyl group, a 2-propenyl group or a 3-pentenyl group.
The liquid crystal composition has slightly different properties such as dielectric anisotropy Delta epsilon, optical anisotropy Delta n, transition temperature point CP of liquid crystal nematic phase converted into liquid and stability at low temperature, but has the same characteristic of rotary viscosity gamma 1 Lower. The liquid crystal display device can realize quick response. The liquid crystal composition has high stability to heat and light. The liquid crystal display element or the liquid crystal display comprising the liquid crystal composition has the properties of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like. PSVA liquid crystal compositions suitable for display or TV applications, in particular, show no or significantly reduced image sticking after long run times.
The liquid crystal compound provided by the invention can also be added with dopants with various functions, the content of the dopants is preferably 0.01-1%, and the dopants are mainly antioxidants, ultraviolet absorbers and chiral agents.
The antioxidant and the ultraviolet absorber are preferably:
s represents an integer of 1 to 10.
The invention also relates to a liquid crystal display element or a liquid crystal display comprising any one of the liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
The liquid crystal display element or liquid crystal display is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
The active matrix display element or the display is specifically a PSVA-TFT or IPS-TFT liquid crystal display element or display.
Drawings
FIG. 1 is a spectrum of a compound b-2 in example 2.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
The progress of the reaction is generally monitored by TLC, and the post-treatment after the completion of the reaction is generally water washing, extraction, combination of organic phases, drying, evaporation of the solvent under reduced pressure, recrystallization and column chromatography, and those skilled in the art can implement the present invention as described below.
The percentages in the specification are mass percentages, the temperature is centigrade (DEG C), and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
S-N represents the crystalline to nematic melting point (. Degree. C.) of the liquid crystal;
Δ n represents optical anisotropy, n o Refractive index of ordinary rays, n e The refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ ε represents the dielectric anisotropy, Δ ε = ε ∥ -ε ⊥ Wherein epsilon ∥ Is a dielectric constant parallel to the molecular axis,. Epsilon ⊥ The dielectric constant is perpendicular to the molecular axis, the test conditions are 25 +/-0.5 ℃, 20-micron parallel boxes are tested, and INSTEC is ALCT-IR 1;
rho represents resistivity (omega cm), the test condition is 25 +/-2 ℃, and the test instrument is a TOYO SR6517 high-impedance instrument and an LE-21 liquid electrode.
VHR represents the voltage holding ratio (%), and the test conditions are 20 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7ms. The testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester.
Tau represents the response time (ms), the test instrument is DMS-501, the test condition is 25 +/-0.5 ℃, the test box is a 3.3-micron IPS test box, the electrode spacing and the electrode width are both 10 microns, and the included angle between the friction direction and the electrode is 10 degrees.
T (%) represents transmittance, T (%) =100% bright state (Vop) luminance/light source luminance, test device DMS501, test conditions 25 ± 0.5 ℃, test cell is 3.3 μm IPS test cell, electrode pitch and electrode width are both 10 μm, and rubbing direction and electrode angle are 10 °.
A synthetic route for compounds of formula I:
k represents H, CH 3 、CF 3
Triethylamine and dichloromethane were reacted at room temperature for 4 hours.
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables (I) and (II)
Table (one): corresponding code of ring structure
Table (ii): corresponding codes for end groups and linking groups
Examples are:
example 1
26.6g of (a-1) (0.1 mol) was dissolved in 150ml of methylene chloride, 30.3g of triethylamine was added thereto, 26g of methacryloyl chloride (0.25mol) was added dropwise thereto at room temperature, and the mixture was reacted for four hours with stirring.
Washing with water to remove residual acid.
Evaporating the solvent under reduced pressure, dissolving with petroleum ether, passing through silica gel chromatographic column, and evaporating the solvent. And (5) recrystallizing with absolute ethyl alcohol. 20.1g of (a-2) was obtained in 50% yield, HPLC:98.88%.
Example 2:
raw material is changed into (b-1)
The same synthetic method as example 1 was used to obtain
Example 3:
example 4
The composition can be maintained at-30 deg.C for 1000 hr, has no (b-2) precipitation, and has good low temperature solubility.
Example 5
Under the same UV polymerization conditions: 72mW/cm 2 @365nm，200s；5mW/cm 2 @365nm90min, residual monomer amount (50 ppm) of (b-2) lower than that of the existing RM
(120ppm)。
Example 6
The liquid crystal composition has lower rotational viscosity gamma 1, is used for liquid crystal display, and can realize quick response. Is particularly suitable for liquid crystal materials for PSVA mode.
Claims (8)
1. A polymerizable compound represented by the formula I-1:
2. a liquid crystal composition comprising a compound of formula I-1, one or more compounds of formula II and one or more compounds of formula III,
R 1 、R 2 、R 3 、R 4 each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more unconnected CH in the group shown 2 May be substituted with cyclopentyl, cyclobutyl or cyclopropyl;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-；
m represents 1,2;
n represents 0,1,2.
3. The liquid crystal composition of claim 2, wherein the one or more compounds of formula ii are one or two compounds of formulae ii-1 to ii-14; the one or more compounds shown in the formula III are one or more compounds in the compounds shown in the formulas III-1 to III-11,
wherein R is 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, or a carbon atomAlkoxy with a sub-number of 1-10, alkoxy with a fluorine-substituted carbon number of 1-10, alkenyl with a carbon number of 2-10, alkenyl with a fluorine-substituted carbon number of 2-10, alkenyloxy with a carbon number of 3-8 or alkenyloxy with a fluorine-substituted carbon number of 3-8, and R 3 、R 4 Any one or more unconnected CH in the group shown 2 May be substituted with cyclopentyl, cyclobutyl or cyclopropyl.
4. The liquid crystal composition of claim 2, wherein the liquid crystal composition is a negative liquid crystal composition further comprising one or more compounds of formula IV
Wherein R is 5 、R 6 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more CH of the group 2 May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;
w represents O, S or-CH 2 O-。
5. The liquid crystal composition of claim 2, wherein the liquid crystal composition is a negative liquid crystal composition further comprising one or more compounds of formula V
Wherein R is 7 、R 8 Each independently represents an alkyl group having 1 to 10 carbon atoms or a fluorine-substituted carbon atomAn alkyl group having 1 to 10 sub-atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
6. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 2 to 5; the display element or display is an active matrix display element or display or a passive matrix display element or display.
7. The liquid crystal display element or the liquid crystal display according to claim 6, characterized in that: the active matrix display element or the display is a PS VA-TFT liquid crystal display element or a display.
8. An optically anisotropic body formed from a liquid crystal composition comprising the compound of claim 1.
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| CN109652097B (en) * | 2018-05-18 | 2023-06-02 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| WO2020115089A1 (en) * | 2018-12-07 | 2020-06-11 | Merck Patent Gmbh | Liquid-crystal medium comprising polymerisable compounds and the use thereof in liquid-crystal displays |
| EP3891250A1 (en) * | 2018-12-07 | 2021-10-13 | Merck Patent GmbH | Polymerisable compounds and the use thereof in liquid-crystal displays |
| CN113121349B (en) * | 2021-04-19 | 2022-03-08 | 北京理工大学 | Flame-retardant vinyl ester resin monomer and preparation thereof, flame-retardant vinyl ester resin condensate and preparation thereof |
| CN114957000A (en) * | 2022-06-24 | 2022-08-30 | 陕西科技大学 | Biomass-based active diluent double-bonded magnolol and preparation method and application thereof |
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| EP2243812A2 (en) * | 2009-04-23 | 2010-10-27 | Merck Patent GmbH | Liquid crystal display |
| CN104449760A (en) * | 2013-09-12 | 2015-03-25 | 默克专利股份有限公司 | Liquid crystal medium |
| KR20170008338A (en) * | 2015-07-13 | 2017-01-24 | 삼성디스플레이 주식회사 | Liquid crystal composition and liquid crystal display including the same |
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