CN103773389B - Containing the liquid-crystal composition of pyranylation compound - Google Patents
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Abstract
The present invention relates to a kind of liquid-crystal composition containing pyranylation compound, comprise the compound shown in one or more general formula Is, the compound shown in one or more general formula Is I, the compound shown in one or more general formula III, the compound shown in one or more general formula Is V, the compound shown in one or more general formulas V; Liquid-crystal composition excellent performance provided by the invention, has the features such as the optical anisotropy that rotary viscosity is low, the time of response is fast, nematic phase range is wide, suitable, is applicable in active matrix electrooptic element and liquid-crystal display, can be used for manufacturing TFT-LCD.In each general formula, each parameter has the implication provided in specification sheets,
Description
Technical Field
The invention relates to a liquid crystal composition containing a pyran-based liquid crystal compound, in particular to a liquid crystal composition applied to an active matrix display, especially TN, STN, IPS and VA displays.
Background
Liquid crystal displays using the liquid crystal composition are widely used in displays of instruments, computers, televisions, and the like. In the field of liquid crystal display technology, the market has been very large in recent years, and the technology has become mature. Liquid crystal display elements are classified into the following modes according to display modes: a Twisted Nematic (TN) mode, a Super Twisted Nematic (STN) mode, an in-plane mode (IPS), a Vertical Alignment (VA) mode, a thin film transistor liquid crystal display (TFT-LCD) has become the mainstream of the development of flat panel displays. High-quality TFT-LCDs require high contrast, high definition, high-speed response, high brightness, and a wide viewing angle. In addition, low power consumption is also required. In any display mode, the liquid crystal composition is required to have stable chemical and physical properties, low rotational viscosity, appropriate optical anisotropy Δ n, appropriate dielectric anisotropy Δ, and good compatibility with other liquid crystal compounds.
However, to date, no single liquid crystal monomer has been used alone in liquid crystal displays without being combined with other compounds to meet performance requirements. When two or more liquid crystal monomers are mixed together, various properties of liquid crystals can be continuously changed, and a general commercial liquid crystal composition is basically formed by mixing a plurality of monomer liquid crystals.
The liquid crystal molecule introduces a difluoromethyleneoxy (-CF)2O-) expands the nematic phase temperature range to a great extent, reduces the rotational viscosity gamma 1, and increases the dielectric anisotropy delta of the liquid crystal molecules. Liquid crystal compounds having difluoromethyleneoxy (-CF2O-) with various substituents have been disclosed by German Merck and Japanese Chilean corporation (CN1717468A, CN101143808A, CN101157862A, etc.). After liquid crystal molecules are introduced into a tetrahydropyran ring, oxygen atoms on the ring are introducedThe method increases the dipole moment of molecules, has the function of remarkably increasing the dielectric anisotropy for both positive liquid crystal and negative liquid crystal, and has excellent intermiscibility and low rotational viscosity. In addition, the method can also play a role in increasing the nematic phase temperature zone. Liquid crystal compounds having tetrahydropyran rings with different substituents have been disclosed by Merck in Germany (CN1806028A, CN101506189A, etc.).
Disclosure of Invention
The technical problem to be solved by the invention is to provide a positive dielectric liquid crystal composition, in particular to a liquid crystal composition containing a pyranyl compound, which has the characteristics of low rotational viscosity, quick response time, wide nematic phase range, proper optical anisotropy and the like, is suitable for active matrix electro-optical elements and liquid crystal displays and can be used for manufacturing TFT-LCDs.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the liquid crystal composition containing the pyranyl compound comprises a component A consisting of one or more compounds shown as a general formula I, a component B consisting of one or more compounds shown as a general formula II, a component C consisting of one or more compounds shown as a general formula III, a component D consisting of one or more compounds shown as a general formula IV and a component E consisting of one or more compounds shown as a general formula V;
wherein,
R11、R12each is any one of the groups of (I) to (IV),
①：H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5，
②：C1～C15straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15A linear alkenyloxy group,
③: -CH-one or more of the groups mentioned in (2)2-a group which is substituted by-CH = CH-, -C.ident.C-, -COO-, -OOC-, cyclobutylidene, cyclopentylidene, -O-or-S-and to which the oxygen atom is not directly attached,
fourthly, the method comprises the following steps: any H of the group in (II) or (III) is replaced by F, Cl;
ring A11Is composed of One of (1);
ring A12Ring A13Ring A14Are respectively a single bond, One of (1);
Z11、Z12、Z13are each a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-CF = CF-;
a. b, c and d are respectively 0, 1, 2 and 3, and a + b + c + d is less than or equal to 5;
R21、R22、R31、R32、R41、R42、R51、R52are respectively F, Cl, CN, C1～C7Straight chain alkyl, C1～C7Straight-chain alkoxy radical, C2～C7Straight chain alkenyl, C1～C5A linear fluoroalkoxy group;
ring A21Ring A22Ring A31Ring A41Ring A42Ring A51Ring A52Ring A53Are respectively a single bond, One of (1);
Z51are each a single bond, -CH2-、-CH2-CH2-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-one of the above;
L21、L22、L41respectively one of H, F, Cl and CN;
e. f, g, h, i and j are respectively 0, 1 and 2.
The invention is further improved in that:
R11is H, C1～C15Straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15One of the linear alkenyloxy groups is,
R12is H, Cl, F, CN, OCN, OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5、C1～C15Straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15One of the linear alkenyloxy groups is,
Z11、Z12、Z13are each a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-one of the above.
The invention is further improved in that: in the liquid crystal composition, the component A accounts for 1-40 wt% of the liquid crystal composition, the component B accounts for 1-60 wt% of the liquid crystal composition, the component C accounts for 10-70 wt% of the liquid crystal composition, the component D accounts for 1-30 wt% of the liquid crystal composition, the component E accounts for 1-50 wt% of the liquid crystal composition, and the components A, B, C, D and E account for 100 wt%.
The invention is further improved in that: in the liquid crystal composition, the component A accounts for 8-19 wt%, the component B accounts for 5-40 wt%, the component C accounts for 33-49 wt%, the component D accounts for 3-10 wt%, and the component E accounts for 5-30.5 wt%.
Due to the adoption of the technical scheme, the technical progress of the invention is as follows:
the compound represented by the general formula I has general physical properties required by liquid crystal monomer compounds, is stable to light and heat, has a wide nematic phase range, and has good compatibility with other compounds, especially the compound represented by the general formula IThe compound has high optical anisotropy delta n, high dielectric anisotropy (delta > 0) and low rotational viscosity gamma1The characteristic of (2) can effectively reduce the threshold voltage of the mixed liquid crystal, and simultaneously quicken the response time and improve the low-temperature intersolubility of the mixed liquid crystal.
The nematic phase type liquid crystal composition obtained by the invention has excellent performance, very low total response time, lower voltage, high resistivity and voltage holding ratio. By adjusting the content of each component, the nematic phase type liquid crystal composition can have different threshold voltages and birefringence characteristics, can be made into various systems commonly used by customers, and is convenient to use under different liquid crystal box thicknesses and different driving voltages. And the liquid crystal composition can still show high resistivity after high temperature, and the liquid crystal composition shows excellent high temperature and ultraviolet stability. Meanwhile, the liquid crystal composition in the embodiment also shows low viscosity, fast response time, proper optical anisotropy and proper dielectric anisotropy, so that the liquid crystal composition can be applied to an electro-optical display with active matrix addressing.
The invention relates to a pyranyl difluoro methylene oxygen bridge ether monomer which is developed and used in a liquid crystal composition, wherein the pyranyl difluoro methylene ether compound is a brand new compound, and is developed and used in the liquid crystal composition for the first time, so that similar liquid crystal compositions are not reported at all. The pyranyl difluoromethyleneoxy ether monomer has pioneering significance in developing liquid crystal materials with excellent performance, and the developed liquid crystal composition has excellent performance. The material is of great value for liquid crystal materials for high-end TFT displays.
The liquid crystal composition can be used for active matrix displays, preferably matrix addressing through Thin Film Transistors (TFTs), is particularly suitable for manufacturing active matrix TN-TFT, IPS-TFT or FFS liquid crystal display elements and liquid crystal displays with quick response, and also belongs to the protection scope of the invention.
Detailed Description
The invention will be further illustrated with reference to the following specific examples:
the specific meanings of the symbols in the examples and the test conditions were as follows:
cp: clearing points, unit ℃;
Δ n: optical anisotropy, wherein Δ n = no-ne, wherein no is the refractive index of ordinary light, ne is the refractive index of extraordinary light, and the test conditions are 589nm and 25 +/-0.5 ℃;
Δ: dielectric anisotropy, Δ =//-⊥Wherein//is the dielectric constant parallel to the molecular axis,⊥the dielectric constant perpendicular to the molecular axis, the test conditions were 25 + -0.5 ℃; 1 KHz; HP 4284A; 5.2 micron TN levorotatory box;
γ1: rotational viscosity in mPas units, test conditions 25. + -. 0.5 ℃.
The liquid crystal composition containing the pyranyl compound comprises a component A consisting of one or more compounds shown as a general formula I, a component B consisting of one or more compounds shown as a general formula II, a component C consisting of one or more compounds shown as a general formula III, a component D consisting of one or more compounds shown as a general formula IV and a component E consisting of one or more compounds shown as a general formula V;
wherein,
R11、R12each is any one of the groups of (I) to (IV),
①：H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5，
②：C1～C15straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15A linear alkenyloxy group,
③: ② a group wherein one or more of the radicals-CH 2-are replaced by-CH = CH-, -C.ident.C-, -COO-, -OOC-, cyclobutylidene, cyclopentylidene, -O-or-S-and the oxygen atoms are not directly attached,
fourthly, the method comprises the following steps: any H of the group in (II) or (III) is replaced by F, Cl;
ring A11Is composed of One of (1);
ring A12Ring A13Ring A14Are respectively a single bond, One of (1);
Z11、Z12、Z13are each a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-CF = CF-;
a. b, c and d are respectively 0, 1, 2 and 3, and a + b + c + d is less than or equal to 5;
R21、R22、R31、R32、R41、R42、R51、R52are respectively F, Cl, CN, C1～C7Straight chain alkyl, C1～C7Straight-chain alkoxy radical, C2～C7Straight chain alkenyl, C1～C5A linear fluoroalkoxy group;
ring A21Ring A22Ring A31Ring A41Ring A42Ring A51Ring A52Ring A53Are respectively a single bond, One of (1);
Z51are each a single bond, -CH2-、-CH2-CH2-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-one of the above;
L21、L22、L41respectively one of H, F, Cl and CN;
e. f, g, h, i and j are respectively 0, 1 and 2.
Preferably, the first and second electrodes are formed of a metal,
R11is H, C1～C15Straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15One of the linear alkenyloxy groups is,
R12is H, Cl, F, CN, OCN, OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5、C1～C15Straight chain alkyl, C1～C15Straight-chain alkoxy radical, C2～C15Straight chain alkenyl, C2～C15One of the linear alkenyloxy groups is,
Z11、Z12、Z13are each a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-one of the above.
In the liquid crystal composition containing the pyranyl compound, the component A in the liquid crystal composition accounts for 1-40% by weight of the liquid crystal composition, and preferably 8-19% by weight of the liquid crystal composition; the component B accounts for 1 to 60 percent of the weight of the liquid crystal composition, preferably 5 to 40 percent; the component C accounts for 10 to 70 percent of the weight of the liquid crystal composition, and preferably 33 to 49 percent; the component D accounts for 1 to 30 percent of the weight of the liquid crystal composition, and preferably 3 to 10 percent; the component E accounts for 1 to 50 percent of the weight of the liquid crystal composition, preferably 5 to 30.5 percent; the weight percentage of the component A, the component B, the component C, the component D and the component E is 100 percent.
The compound shown in the general formula I in the liquid crystal composition containing the pyranyl compound can preferably be one or more of the compounds shown in the following formulas I-1 to I-4, the compound shown in the general formula II can preferably be one or more of the compounds shown in the following formulas II-1 to II-10, the compound shown in the general formula III can preferably be one or more of the compounds shown in the following formulas III-1 to III-4, the compound shown in the general formula IV can preferably be one or more of the compounds shown in the following formulas IV-1 to IV-4, the compound shown in the general formula V is specifically one or more of the compounds shown in the following formulas V-1 to V-12,
wherein,
ring A11Is composed ofIn the above-mentioned manner, the first and second substrates are,
R11is H or C1～C10One of the linear alkyl groups of (a),
R12is F, Cl, OCF3、CF3One of CN and NCS,
(F) is H or F.
The compound shown in the general formula I in the liquid crystal composition containing the pyranyl compound can further preferably be one or more compounds shown in the following formulas I-1-1 to I-4-6,
wherein,
R11is H, CH3、C2H5、C3H7、n-C4H9、n-C5H11、n-C6H13One kind of (1).
The components used in examples 1 to 5 below can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional and the resulting liquid crystal compounds are tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the weight percentages of the liquid crystal compositions specified in examples 1 to 5 below. The liquid crystal composition is prepared according to the conventional method in the field, for example, the liquid crystal composition is prepared by mixing according to the specified proportion by adopting the modes of heating, ultrasonic wave, suspension and the like.
Example 1
The liquid crystal composition is prepared from the following compounds in percentage by weight,
the liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test, and the test result is that Cp: 87 ℃; Δ n: 0.105; Δ: 7.2; gamma ray1：65mPa·s；
The liquid crystal composition has high clearing point, moderate optical anisotropy, proper high dielectric anisotropy and low rotational viscosity, so that the liquid crystal composition is very suitable for TN-TFT and IPS-TFT displays with quick response.
Example 2
The liquid crystal composition is prepared from the following compounds in percentage by weight,
the liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test, and the test result is that Cp: 94 ℃; Δ n: 0.125; Δ: 7.8 of; gamma ray1：65mPa·s；
The liquid crystal composition has higher clearing point, slightly higher optical anisotropy, properly higher dielectric anisotropy and very low rotational viscosity, so that the liquid crystal composition is very suitable for a TN-TFT display with quick response.
Example 3
The liquid crystal composition is prepared from the following compounds in percentage by weight,
filling the liquid crystal compositionThe performance test was performed between the two substrates of the lcd, and the test results were Cp: 87 ℃; Δ n: 0.105; Δ: 7.2; gamma ray1：65mPa·s；
The liquid crystal composition has high clearing point, moderate optical anisotropy, proper high dielectric anisotropy and low rotational viscosity, so that the liquid crystal composition is very suitable for an IPS-TFT (in-plane switching-thin film transistor) display with quick response.
Example 4
The liquid crystal composition is prepared from the following compounds in percentage by weight,
the liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test, and the test result is that Cp: 87 ℃; Δ n: 0.112; Δ: 7.7; gamma ray1：65mPa·s；
The liquid crystal composition has higher clearing point, higher optical anisotropy, properly high dielectric anisotropy and very low rotational viscosity, so the liquid crystal composition is very suitable for the IPS-TFT display with quick response.
Example 5
The liquid crystal composition is prepared from the following compounds in percentage by weight,
the liquid crystal composition is filled between two substrates of a liquid crystal display to carry out performance test, and the test result is that Cp: 87 ℃; Δ n: 0.110; Δ: 6.9; gamma ray1：63mPa·s；
The liquid crystal composition has high clearing point, moderate optical anisotropy, proper high dielectric anisotropy and very low rotational viscosity, so that the liquid crystal composition is very suitable for a TN-TFT display with quick response.
The above 5 examples all have good low temperature stability, low rotational viscosity, and maintain fast response time in the low temperature region. The liquid crystal display panel can broaden the use temperature of a TN-TFT, an IPS-TFT or an FFS-TFT liquid crystal mode, has faster response time and wider viewing angle range, and is very suitable for TN-TFT, IPS-TFT and FFS-TFT display.
The liquid crystal composition provided by the invention has the effects of reducing threshold voltage and response time by using the pyran group-containing difluoromethylene ether compounds, so that the liquid crystal composition developed by the invention is an ideal liquid crystal material for preparing a TFT liquid crystal display with quick response.
Although the present invention only exemplifies the specific compounds and the proportioning amounts (weight percentage content) of the above 5 embodiments, and performs the performance test, the liquid crystal composition of the present invention can be further extended and modified by using the liquid crystal compounds represented by the general formulas I, II, III, and IV and the preferred liquid crystal compounds of the general formulas I, II, III, and IV based on the above embodiments, and the object of the present invention can be achieved by properly adjusting the proportioning amounts.
Claims (3)
1. A liquid crystal composition containing a pyranyl compound is characterized in that:
comprises a component A consisting of one or more compounds shown in general formulas I-1 to I-4, a component B consisting of one or more compounds shown in general formulas II-1 to II-10, a component C consisting of one or more compounds shown in general formulas III-1 to III-4, a component D consisting of one or more compounds shown in general formulas IV-1 to IV-3 and a component E consisting of one or more compounds shown in general formulas V-1 to V-12; in the liquid crystal composition, the component A accounts for 1-40 wt% of the liquid crystal composition, the component B accounts for 1-60 wt% of the liquid crystal composition, the component C accounts for 10-70 wt% of the liquid crystal composition, the component D accounts for 1-30 wt% of the liquid crystal composition, the component E accounts for 1-50 wt% of the liquid crystal composition, and the components A, B, C, D and E account for 100 wt%;
wherein:
R11is H, C1～C10One of linear alkyl;
R12is Cl, F, CN, OCF3、CF3One of NCS;
ring A11Is composed ofOne of (1);
R21、R22、R31、R32、R41、R42、R51、R52are respectively F, Cl, CN, C1～C7Straight chain alkyl, C1～C7Straight-chain alkoxy radical, C2～C7Straight chain alkenyl, C1～C5A linear fluoroalkoxy group;
(F) is H or F.
2. The liquid crystal composition containing a pyranyl compound as claimed in claim 1, wherein:
the compound shown in the general formula I is one or more of the compounds shown in the following formulas I-1-4-6,
wherein,
R11is H, CH3、C2H5、C3H7、n-C4H9、n-C5H11、n-C6H13One kind of (1).
3. The liquid crystal composition containing a pyranyl compound as claimed in claim 1, wherein: in the liquid crystal composition, the component A accounts for 8-19 wt%, the component B accounts for 5-40 wt%, the component C accounts for 33-49 wt%, the component D accounts for 3-10 wt%, and the component E accounts for 5-30.5 wt%.
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