CN113736479A - Negative dielectric anisotropy liquid crystal composition and liquid crystal display device - Google Patents
Negative dielectric anisotropy liquid crystal composition and liquid crystal display device Download PDFInfo
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- 125000000217 alkyl group Chemical group 0.000 claims description 47
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- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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- 125000006193 alkinyl group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
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- 239000003505 polymerization initiator Substances 0.000 claims description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000006023 1-pentenyl group Chemical group 0.000 description 5
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 4
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 4
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 description 4
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- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000011056 performance test Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- Crystallography & Structural Chemistry (AREA)
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Abstract
The invention relates to a negative dielectric anisotropy liquid crystal composition and a liquid crystal display device. The negative dielectric anisotropic liquid crystal composition of the present invention comprises: at least one compound represented by formula I; at least one compound represented by formula II. Compared with the prior art, the liquid crystal composition has the technical effects of good response speed and high transmittance on the basis of maintaining proper optical anisotropy value and dielectric anisotropy.
Description
Technical Field
The invention relates to the technical field of liquid crystal materials. And more particularly, to a liquid crystal composition and a liquid crystal display device.
Background
Liquid crystal display devices are used in various household electric appliances, industrial measuring instruments, automobile panels, mobile phones, smart phones, notebook personal computers, tablet PCs, televisions, and the like, as typified by clocks and desktop computers. Representative examples of liquid crystal display systems include: twisted Nematic (TN) type, Super Twisted Nematic (STN) type, guest-host (GH) type, in-plane switching (IPS) type, Fringe Field Switching (FFS) type, Optically Compensated Birefringence (OCB) type, Electrically Controlled Birefringence (ECB) type, Vertically Aligned (VA) type, Color Super Homeotropic (CSH) type, Ferroelectric Liquid Crystal (FLC) type, and the like. The driving method may be static driving, multiplex driving, simple matrix driving, or Active Matrix (AM) driving by a Thin Film Transistor (TFT), a Thin Film Diode (TFD), or the like. Among these display modes, it is known that when a liquid crystal composition (n-type liquid crystal composition) exhibiting a negative dielectric anisotropy is used, the IPS mode, FFS mode, ECB mode, VA mode, CSH mode, and the like exhibit favorable characteristics.
The display modes using the n-type liquid crystal composition include a vertical Alignment mode represented by a Polymer Stabilized Alignment (PSA) type or a Polymer Stabilized vertical Alignment (PS-VA) type in which Alignment is controlled by polymerizing a VA-type or a polymerizable compound in a liquid crystal phase, and a horizontal Alignment mode represented by an IPS-type or FFS-type. The vertical alignment method is characterized by a wide viewing angle, high transmittance, high contrast, and a high response speed, and is mainly used for large-sized display devices such as Televisions (TVs) and monitors. On the other hand, the horizontal alignment method is adopted in mobile devices such as smartphones and tablet PCs, and is also being adopted in liquid crystal televisions from the viewpoint of a wide viewing angle, high transmittance, low power consumption, and optimality with respect to touch panels. The PSA-type or PS-VA-type liquid crystal display device is a device in which a polymer structure is formed in a cell in order to control a pretilt angle of liquid crystal molecules, and is known to have a high-speed response and a high contrast ratio particularly in the characteristics of a vertical alignment method.
In recent years, with the progress of high resolution, high frequency driving, and the like of liquid crystal TVs, there has been an increasing demand for liquid crystal compositions that are suitable for high-performance liquid crystal devices and can satisfy various characteristics.
Further, there is a problem that a liquid crystal composition containing a polymerizable compound, which has been conventionally used to contain a polymerizable compound in a liquid crystal composition, does not have characteristics capable of coping with a high-resolution liquid crystal TV such as 4K or 8K. In particular, a high-resolution liquid crystal display device requires high-definition pixels each having a small size. Since the area of the wiring and the light shielding portion is relatively increased, Ultraviolet (UV) light is largely blocked, and the aperture ratio of the liquid crystal display portion is reduced, thereby lowering the transmittance.
In particular, in the case of a vertical alignment liquid crystal display device (hereinafter, sometimes referred to as "VA liquid crystal display device"), it is difficult to sufficiently improve light transmittance only by adjusting the threshold voltage. By shifting (shift) the V-T curve showing the characteristics of applied voltage-transmittance to the low voltage side by lowering the threshold voltage, the transmittance under the low voltage condition can be improved. However, in the above method, the slope of the V-T curve of the VA liquid crystal display device does not become steep, and the maximum transmittance does not become high, so that it is difficult to achieve high light transmittance at a middle-order or higher driving voltage.
Regarding the liquid crystal composition constituting the liquid crystal layer, adjustment of splay elastic constant (K) is considered11) And bending elastic constant (K)33) Is K11/K33The method of (2). By adjusting so that K11/K33The value of (3) is reduced, the V-T curve of the corresponding VA liquid crystal display device becomes steep, and the light transmittance can be improved even if the driving voltage is higher than the medium-order.
In addition, in liquid crystal TVs of higher models and the like, high-frequency driving is progressing, and therefore development of a liquid crystal composition capable of responding to voltage change at high speed is urgently required. In order to respond to the voltage change at high speed, it is desirable that G as a parameter that governs the response speed in a liquid crystal display device of a vertical alignment mode (such as VA mode or the like)1/K33The value of (c) is small. In a liquid crystal display device of a horizontal alignment mode (such as an IPS mode), G, which is a parameter that governs response speed, is desirable1/K11The value of (c) is small.
Disclosure of Invention
The present inventors have found in their studies that the elastic constant K is higher in a liquid crystal composition11、K33Is a parameter having a high correlation with each other, K11Reduction of simultaneous K33And will be reduced accordingly. Therefore, it is considered to reduce the rotational viscosity G1Rather than increasing the elastic constant K33Or K11To realize G1/K33Or G1/K11A decrease in value.
The present inventors have further studied and found that a negative dielectric anisotropy liquid crystal composition of the present invention containing the liquid crystal compounds represented by the above formulas I and II has a rotational viscosity G in addition to various properties required for an n-type liquid crystal composition having a negative dielectric anisotropy (. DELTA.. di-elect cons.) in consideration of the properties required for the n-type liquid crystal composition1Sufficiently small and K is sufficient in a liquid crystal display device of a vertical alignment mode (e.g., VA mode, etc.)11/K33、G1/K33Has a small value of K in a liquid crystal display device of a horizontal alignment mode (e.g., IPS mode, etc.)11/K33、G1/K11The values of (A) are all small, and when the liquid crystal display device is used for liquid crystal devices such as liquid crystal TVs, quick response and high transmittance can be realized. Thus, the present invention has been completed.
In one aspect, the present invention provides a negative dielectric anisotropic liquid crystal composition comprising:
at least one compound represented by formula I; and the number of the first and second groups,
at least one compound represented by formula II;
in the formula I, R1、R2Each independently represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a linear alkenyl group having 2 to 8 carbon atoms, or a linear alkenyloxy group having 2 to 8 carbon atoms, wherein one or two of-CH groups are not adjacent to each other2-optionally substituted by-O-, wherein any H is optionally substituted by a F atom;
Z1、Z2each independently represents-C2H2-、-C2H4-、-C2H2CH2O-、-OCH2C2H2-、-CH2O-、-OCH2-、-C2H2CH2S-、-SCH2C2H2-、-CH2S-、-SCH2-、-O-、-S-、-CF2O-、-OCF2-, -C.ident.C-, -OOC-or-COO-, the aforementioned-CH2O-、-C2H2-、-C2H4-、-C2H2CH2O-, or-OCH2C2H2-any H in (a) is optionally substituted with F;
x represents-O-, -S-, -SO-, -SOO-, -CF2-, -CO-or-CH2-；
Y1、Y2Each independently represents-F-, -OCH2F-、-OCHF2-or-OCF3-, in which Y1、Y2Does not simultaneously represent-F-;
n represents 0, 1, 2 or 3;
in the formula II, R3、R4Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms; and, R3、R4Each independently of the other, H on any carbon atom in (a) is optionally substituted with F;
p represents 0, 1 or 2.
In another aspect, the present invention provides a liquid crystal display device using the aforementioned negative dielectric anisotropy liquid crystal composition of the present invention.
Effects of the invention
By using the negative dielectric anisotropic liquid crystal composition of the present invention containing the liquid crystal compounds represented by the above formulas I and II, K is satisfied with various properties required for the liquid crystal composition having negative dielectric anisotropy11/K33、G1/K33Or G1/K11The value is reduced, and thus, a liquid crystal display device using the negative dielectric anisotropy liquid crystal composition of the present invention can realize a fast response and a high transmittance. The negative dielectric anisotropic liquid crystal composition of the present invention can obtain reduced G in a vertical alignment mode (e.g., VA, PS-VA)1/K33And a parameter that governs steepness of the electro-optic effect, namely, K11/K33Reduced to have an improved response speed and excellent transmittance. The negative dielectric constant anisotropic liquid crystal composition of the present invention can obtain a reduced G in a liquid crystal display device in a horizontal alignment mode (e.g., IPS)1/K11And a parameter that governs the steepness of the electro-optical effect, namely K33/K11Is large, thereby having an improved response speed and excellent transmittance.
Detailed Description
[ liquid Crystal composition ]
The negative dielectric anisotropic liquid crystal composition of the present invention comprises:
at least one compound represented by formula I; and the number of the first and second groups,
at least one compound represented by formula II;
in the formula I, R1、R2Each independently represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a linear alkenyl group having 2 to 8 carbon atoms, or a linear alkenyloxy group having 2 to 8 carbon atoms, wherein one or two of-CH groups are not adjacent to each other2-optionally substituted by-O-, wherein any H is optionally substituted by a F atom;
Z1、Z2each independently represents-C2H2-、-C2H4-、-C2H2CH2O-、-OCH2C2H2-、-CH2O-、-OCH2-、-C2H2CH2S-、-SCH2C2H2-、-CH2S-、-SCH2-、-O-、-S-、-CF2O-、-OCF2-, -C.ident.C-, -OOC-or-COO-, the aforementioned-CH2O-、-C2H2-、-C2H4-、-C2H2CH2O-, or-OCH2C2H2-any H in (a) is optionally substituted with F;
x represents-O-, -S-, -SO-, -SOO-, -CF2-, -CO-or-CH2-；
Y1、Y2Each independently represents-F-, -OCH2F-、-OCHF2-or-OCF3-, in which Y1、Y2Does not simultaneously represent-F-;
n represents 0, 1, 2 or 3;
in the formula II, R3、R4Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms; and, R3、R4Each independently of the other, H on any carbon atom in (a) is optionally substituted with F;
p represents 0, 1 or 2.
As the aforementioned R1、R2Examples of the "straight-chain alkyl group having 1 to 8 carbon atoms" independently of each other include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups. From the viewpoint of obtaining excellent response time and transmittance, methyl, ethyl, or propyl is more preferable.
As the aforementioned R1、R2Examples of the "linear alkoxy group having 1 to 8 carbon atoms" independently of each other include methoxy, ethoxy and n-methoxyPropoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, and the like. From the viewpoint of obtaining excellent response time and transmittance, a methoxy group, an ethoxy group, or an n-propoxy group is more preferable.
As the aforementioned R1、R2Examples of the "straight-chain alkenyl group having 2 to 8 carbon atoms" independently of each other include an ethenyl group, a propenyl group, a butenyl group, a 1-pentenyl group, and a 2-pentenyl group. From the viewpoint of obtaining excellent response time and transmittance, a linear alkenyl group having 2 to 5 carbon atoms is preferable, and an ethenyl group or an propenyl group is more preferable.
As the aforementioned R1、R2Examples of the "linear alkenyloxy group having 2 to 8 carbon atoms" independently of each other include an vinyloxy group, a propenyloxy group, a butenyloxy group, a 1-pentenyloxy group, and a 2-pentenyloxy group. From the viewpoint of obtaining excellent response time and transmittance, a linear alkenyloxy group having 2 to 5 carbon atoms is preferable, and an ethyleneoxy group or propyleneoxy group is more preferable.
R mentioned above1、R2The "straight-chain alkyl group having 1 to 8 carbon atoms", "straight-chain alkoxy group having 1 to 8 carbon atoms", "straight-chain alkenyl group having 2 to 8 carbon atoms", or "straight-chain alkenyloxy group having 2 to 8 carbon atoms" represented by the formula (I) wherein one or two of-CH groups are not adjacent to each other2-is optionally substituted by-O-, wherein any H is optionally substituted by a F atom.
The aforementioned n represents 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 or 1.
As the aforementioned R3、R4The "alkyl group having 1 to 5 carbon atoms" may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and is preferably a straight-chain alkyl group. Examples of such a straight-chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group. From the viewpoint of obtaining excellent response time and transmittance, methyl, ethyl, or propyl is more preferable.
As the aforementioned R3、R4The "C1-5Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, n-pentoxy and tert-pentoxy. From the viewpoint of obtaining excellent response time and transmittance, a methoxy group, an ethoxy group, or an n-propoxy group is more preferable.
As the aforementioned R3、R4Examples of the "alkenyl group having 2 to 5 carbon atoms" include an ethenyl group, a propenyl group, a butenyl group, a 2-methylpropenyl group, a 1-pentenyl group, a 2-methyl-1-butenyl group, a 3-methyl-1-butenyl group, and a 2-methyl-2-butenyl group. From the viewpoint of obtaining excellent response time and transmittance, an ethylene group or an propylene group is more preferable.
As the aforementioned R3、R4Examples of the "alkenyloxy group having 2 to 5 carbon atoms" include an vinyloxy group, a propenyloxy group, a butenyloxy group, a 2-methylpropenyloxy group, a 1-pentenyloxy group, a 2-methyl-1-butenyloxy group, a 3-methyl-1-butenyloxy group, and a 2-methyl-2-butenyloxy group. From the viewpoint of obtaining excellent response time and transmittance, an ethyleneoxy group or propyleneoxy group is more preferable.
R mentioned above3、R4The "alkyl group having 1 to 5 carbon atoms", "alkoxy group having 1 to 5 carbon atoms", "alkenyl group having 1 to 5 carbon atoms" and "alkenyloxy group having 1 to 5 carbon atoms" are represented by the formula, wherein H on any carbon atom is optionally substituted by F.
In some embodiments of the negative dielectric anisotropy liquid crystal composition of the present invention, preferably, the aforementioned compound of formula I is selected from the group consisting of compounds of formulae IA to IZK, Ia to Izk, wherein R is1、R2The definitions of (a) are the same as those described above.
More preferably, the compound represented by the formula I is selected from the group consisting of compounds represented by the following formulae IA-1 to IZK-4 and Ia-1 to Izk-4, wherein each Alkyl group independently represents a straight-chain Alkyl group having C1 to C8, and each alkinyl group independently represents a straight-chain Alkenyl group having C2 to C8.
In some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention, preferably, the aforementioned compound represented by formula II is selected from the group consisting of the compounds represented by formulae II-1 to II-10 below.
Wherein R is3、R4The above definitions are the same as above, and each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms; r3、R4Each hydrogen on any carbon atom in (a) is independently optionally substituted with fluorine;
(F) represents F or H.
In some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention, one or more compounds represented by formula iii below may be further included:
R5、R6each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms,An alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms; and, R5、R6Each independently of the other, H on any carbon atom in (a) is optionally substituted with F;
Z3represents a single bond or-CH2O-；
q and r each independently represent 0, 1 or 2;
as the aforementioned R5、R6The "alkyl group having 1 to 5 carbon atoms" may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and is preferably a straight-chain alkyl group. Examples of such a straight-chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group. More preferably methyl, ethyl or propyl.
As the aforementioned R5、R6Examples of the "alkoxy group having 1 to 5 carbon atoms" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, n-pentoxy, and tert-pentoxy. Further preferred is a methoxy group, an ethoxy group or a n-propoxy group.
As the aforementioned R5、R6Examples of the "alkenyl group having 2 to 5 carbon atoms" include an ethenyl group, a propenyl group, a butenyl group, a 2-methylpropenyl group, a 1-pentenyl group, a 2-methyl-1-butenyl group, a 3-methyl-1-butenyl group, and a 2-methyl-2-butenyl group. Further preferred is an ethylene group or a propylene group.
As the aforementioned R5、R6Examples of the "alkenyloxy group having 2 to 5 carbon atoms" include an vinyloxy group, a propenyloxy group, a butenyloxy group, a 2-methylpropenyloxy group, a 1-pentenyloxy group, a 2-pentenyloxy group, and a 2-methylpropenyloxy group-1-butenyloxy, 3-methyl-1-butenyloxy, 2-methyl-2-butenyloxy and the like. Further preferred is an ethyleneoxy group or a propyleneoxy group.
R mentioned above5、R6The "alkyl group having 1 to 5 carbon atoms", "alkoxy group having 1 to 5 carbon atoms", "alkenyl group having 1 to 5 carbon atoms" and "alkenyloxy group having 1 to 5 carbon atoms" are represented by the formula, wherein H on any carbon atom is optionally substituted by F.
Among the aforementioned compounds represented by the formula III, it is preferable that they are selected from the group consisting of the compounds represented by the following formulae III-1 to III-17.
R5、R6The definitions of (a) are the same as those described above.
Some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention may further comprise one or more compounds represented by the following formulae IV-1 to IV-50.
Wherein R is1' represents H or an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and optionally 4 or less of H are substituted by F;
R2' represents H or alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two non-adjacent-CH2-is optionally substituted by-O-, and optionally 4 or fewer H are substituted by F.
As the aforementioned R1The "alkyl group having 1 to 8 carbon atoms" referred to in the above paragraph may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and is preferably a straight-chain alkyl group. Examples of such a straight-chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group. More preferably methyl, ethyl or propyl.
As the aforementioned R1Examples of the "alkenyl group having 2 to 8 carbon atoms" include an ethenyl group, a propenyl group, a butenyl group, a 2-methylpropenyl group, a 1-pentenyl group, a 2-methyl-1-butenyl group, a 3-methyl-1-butenyl group, a 2-methyl-2-butenyl group, a pentenyl group, a hexenyl group, and a heptenyl group. The alkenyl group preferably has 2 to 6 carbon atoms, and more preferably has 2 to 4 carbon atoms.
R mentioned above1In the "alkyl group having 1 to 8 carbon atoms" and the "alkenyl group having 2 to 8 carbon atoms" mentioned above, 4 or less of H are optionally substituted by F.
As the aforementioned R2The "alkyl group having 1 to 8 carbon atoms" referred to in the above paragraph may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and is preferably a straight-chain alkyl group. Examples of such a straight-chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group. More preferably methyl, ethyl or propyl.
As the aforementioned R2Examples of the "alkenyl group having 2 to 8 carbon atoms" include an ethenyl group, a propenyl group, a butenyl group, a 2-methylpropenyl group, and a 1-pentenyl group2-pentenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, pentenyl, hexenyl, heptenyl and the like. The alkenyl group preferably has 2 to 6 carbon atoms, and more preferably has 2 to 4 carbon atoms.
R mentioned above2One or two non-adjacent-CH groups in the "alkyl group having 1 to 8 carbon atoms" and "alkenyl group having 2 to 8 carbon atoms" mentioned in the above2-is optionally substituted by-O-, and optionally 4 or fewer H are substituted by F.
Some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention may further comprise one or more compounds represented by the following formulas V-1 to V-8:
in some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention, the content of the compound represented by formula I may be, for example, 1 to 50% by weight, based on the total amount of the liquid crystal composition, and is preferably 1 to 40%, and more preferably 10 to 40% in terms of obtaining suitable Δ n, Δ ∈, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention, the content of the compound represented by formula II may be, for example, 1 to 60% by weight based on the total amount of the liquid crystal composition, and is preferably 10 to 50%, and more preferably 20 to 50% in terms of obtaining suitable Δ n, Δ ∈, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In some embodiments of the negative dielectric anisotropic liquid crystal composition of the present invention, when the compound represented by formula III is contained, the content of the compound represented by formula III may be 1 to 50% by weight based on the total amount of the liquid crystal composition, and is preferably 10 to 50%, and more preferably 20 to 50% in terms of obtaining suitable Δ n, Δ ∈, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In the negative dielectric anisotropy liquid crystal composition of the present invention, the content of the liquid crystal compound represented by the formula IV is 1 to 50% by weight based on the total amount of the liquid crystal composition, and is preferably 10 to 50%, and more preferably 20 to 50% in terms of obtaining suitable Δ n, Δ ∈, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In one embodiment of the negative dielectric anisotropic liquid crystal composition of the present invention, for example, the liquid crystal composition may contain: 1-50 wt% of a compound shown in formula I, 1-60 wt% of a compound shown in formula II and 1-50 wt% of a compound shown in formula III.
In one embodiment of the negative dielectric anisotropic liquid crystal composition of the present invention, when the compound represented by formula IV is contained, the content of the compound represented by formula IV may be, for example, 1 to 40 parts by mass.
In one embodiment of the negative dielectric anisotropy liquid crystal composition of the present invention, for example, the compound represented by the formula I is 1 to 50 parts by mass, the compound represented by the formula ii is 1 to 60 parts by mass, the compound represented by the formula iii is 1 to 50 parts by mass, and the compound represented by the formula IV is 1 to 40 parts by mass, based on 100 parts by mass of the liquid crystal composition.
In one embodiment of the negative dielectric anisotropic liquid crystal composition of the present invention, when the compound represented by formula V is contained, the content of the compound represented by formula V may be, for example, 0.01 to 1.00 part by mass.
In one embodiment of the negative dielectric anisotropic liquid crystal composition of the present invention, for example, the following components may be contained in the following amounts: the negative dielectric anisotropy liquid crystal composition comprises, based on 100 parts by mass of the negative dielectric anisotropy liquid crystal composition, 1 to 50 parts by mass of the compound represented by the formula I, 1 to 60 parts by mass of the compound represented by the formula II, 1 to 50 parts by mass of the compound represented by the formula III, 1 to 40 parts by mass of the compound represented by the formula IV, and 0.01 to 1.00 part by mass of the compound represented by the formula V.
In the negative dielectric anisotropic liquid crystal composition of the present invention, various functional additives may be optionally added, and these additives may be exemplified by, for example, a UV stabilizer, an antioxidant, a chiral dopant, a polymerization initiator, and may contain one or more of them.
The antioxidant may be exemplified by:
m represents an integer of 1 to 10;
as the chiral dopant, for example,
examples of the light stabilizer include, for example,
Examples of the ultraviolet absorber include,
The additive may be added in an amount of, for example, 0.01 to 1.5% by mass based on the total mass of the liquid crystal composition.
[ liquid Crystal display device ]
The second aspect of the present invention provides a liquid crystal display device using the aforementioned negative dielectric anisotropy liquid crystal composition of the present invention. The liquid crystal display device of the present invention is not particularly limited as long as it contains the liquid crystal composition described above. Those skilled in the art will be able to select other compositions and structures of the liquid crystal display device as appropriate depending on the desired properties.
[ liquid Crystal display device ]
The third aspect of the present invention provides a liquid crystal display device using the aforementioned liquid crystal composition of the present invention. The liquid crystal display device of the present invention is preferably driven in a PS-VA mode, IPS mode, FFS mode, PS-IPS mode, PS-FFS mode, or ECB mode.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method unless otherwise specified, the used raw materials can be obtained from a public commercial way unless otherwise specified, the percentages refer to mass percentage, the temperature is centigrade (DEG C), and the liquid crystal compound is also a liquid crystal monomer.
[ liquid Crystal composition having negative dielectric anisotropy ]
Negative dielectric anisotropy liquid crystal compositions with different compositions are prepared in examples 1 to 9 and comparative examples 1 and 2, wherein the monomer structure, the amount (parts by mass) of the specific compound used in each example, and the performance parameter test results of the obtained liquid crystal medium are respectively shown in the following tables 1 to 11.
The temperature units involved in each example are as follows, and the specific meanings and test conditions of other symbols are as follows:
g1(mpa.s) represents the rotational viscosity coefficient of the liquid crystal compound, and the measurement method: the equipment INSTEC comprises ALCT-IR1, a vertical box with the thickness of 18 microns in a test box, the temperature of 25 ℃, and the short term G1;
K11is a torsional elastic constant, K33For the splay spring constant, the test conditions were: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ ε represents dielectric anisotropy, and Δ ε∥-ε⊥Wherein, epsilon∥Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neFor the refractive index of extraordinary rays, test conditions: 589nm, 25 + -0.2 deg.C.
VHR represents the voltage holding ratio (%) after ultraviolet irradiation, and the test conditions are 20 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7 ms. The testing equipment is a TOYO Model 6254 liquid crystal performance comprehensive tester. In the ultraviolet photopolymerization of the polymerizable compound for VHR test, the ultraviolet photopolymerization is carried out at a wavelength of 313nm and an irradiation light intensity of 0.5Mw/cm2The ultraviolet light of (2) was irradiated for 2 minutes.
Tni: nematic phase-isotropic liquid phase transition temperature (. degree. C.).
Transmittance: the transmittance was measured when a voltage of 0V to 10V was applied to the liquid crystal display cell. When the transmittance is not less than 97%, the transmittance is evaluated as sufficiently high as good, and when the transmittance is less than 97%, the transmittance is evaluated as low as x.
Low-temperature storage property: after cooling the example of the liquid crystal composition containing the polymerizable compound at-20 ℃ for 240 hours, the presence or absence of the deposition of the polymerizable compound was observed as an index of low-temperature storage stability. The case where no precipitation was observed and no display defects such as bright spots were observed was marked as good, and the case where precipitation was observed was marked as "X".
The preparation method of each negative dielectric anisotropy liquid crystal composition in the examples is as follows: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The structures of the liquid crystal monomers used in the examples are represented by the following codes, and the methods for representing the structures of the liquid crystal rings, the terminal groups, and the linking groups are shown in the following tables (one) and (two).
Table (one): corresponding code of ring structure
Table (ii): corresponding codes for end groups and linking groups
Examples are:
liquid crystal compositions of examples 1 to 8 and comparative examples 1 to 2 were prepared in the following formulation ratios shown in tables 1 to 10.
TABLE 1 component proportions of the liquid crystal composition LC-1 of example 1
TABLE 2 component proportions of liquid crystal composition LC-2 of example 2
TABLE 3 component proportioning ratio of liquid crystal composition LC-3 of example 3
TABLE 4 component proportioning ratio of liquid crystal composition LC-4 of example 4
TABLE 5 component proportioning ratio of liquid-crystalline medium LC-5 of example 5
TABLE 6 component proportioning ratio of liquid-crystalline medium LC-6 of example 6
TABLE 7 component proportioning ratio of liquid-crystalline medium LC-7 of example 7
TABLE 8 component proportioning ratio of liquid-crystalline medium LC-8 of example 8
The formulations of comparative example 1 and comparative example 2 are shown in tables 9 and 10 below.
TABLE 9 component ratios of the liquid-crystalline medium C-01 of comparative example 1
TABLE 10 component ratios of the liquid-crystalline medium C-02 of comparative example 2
| The compound of the general formula | Liquid crystal structure | Mass portion of |
| Ⅱ | CC-3-V | 23.0 |
| Ⅱ | PP-1-2V | 10.0 |
| III | CCOY-2-O2 | 16 |
| III | CY-3-O2 | 5.0 |
| III | PY-3-O2 | 14.0 |
| III | CCY-3-O2 | 10.0 |
| III | CPY-3-O2 | 10.0 |
| Ⅱ | CPP-1V-2 | 12.0 |
The liquid crystal compositions of examples 1 to 8 and comparative examples 1 to 2 prepared as described above were filled between two substrates of a liquid crystal display to perform a performance test. The test results are shown in table 11 below.
As shown in Table 11 above, the liquid crystal compositions of examples 1 to 8 had a response speed parameter index G, as compared with the liquid crystal compositions of comparative examples 1 and 21/K33Are all smaller than the comparative examples. Therefore, when the liquid crystal compositions of examples 1 to 8 are used in a liquid crystal display device of a vertical alignment mode (e.g., VA mode, etc.), the response speed is faster.
In addition, the liquid crystal compositions of examples 1 to 8 have a response speed parameter index G, compared with the liquid crystal compositions of comparative examples 1 and 21/K11Are all smaller than the comparative examples. Therefore, when the liquid crystal compositions of examples 1 to 8 are used in a liquid crystal display device of a horizontal alignment mode (e.g., IPS mode), the response speed is higher.
Further, the liquid crystal compositions of examples 1 to 8 have K as compared with the liquid crystal compositions of comparative examples 1 and 211/K33Lower values, increased light transmittance.
Further, the liquid crystal compositions of examples 1 to 8 exhibited more excellent low-temperature storage stability than those of comparative examples 1 and 2.
Further, the liquid crystal compositions of examples 9 to 14 were prepared by mixing the liquid crystal composition prepared in the above example with one of the polymerizable compounds represented by the above formulae (RM-2) and (RM-8). The formulation ratios of the liquid crystal composition and the polymerizable compound are shown in table 12.
TABLE 12 compounding ratios of polymerizable compound-containing liquid crystal compositions of examples 9 to 14
| Example 9 | Example 10 | Example 11 | Example 12 | Example 13 | Example 14 | |
| LC-1 | 99.7 | 99.7 | - | - | - | - |
| LC-2 | - | - | 99.7 | 99.7 | - | - |
| LC-3 | - | - | - | - | 99.7 | 99.7 |
| RM2 | 0.3 | - | 0.3 | - | 0.3 | - |
| RM8 | - | 0.3 | - | 0.3 | - | 0.3 |
Further, Vertically Aligned (VA) liquid crystal display devices were obtained by injecting the polymerizable compound-containing liquid crystal compositions prepared in examples 9 to 14 into ITO-equipped cells each having a cell gap of 3.0 μm and coated with a polyimide alignment film causing vertical alignment, by a vacuum injection method.
The obtained VA liquid crystal display device was used with 100mW/cm while applying a rectangular wave of 10V and 100Hz2A high-pressure mercury lamp with an intensity of (365nm) was used for the exposure of 10J. Further, by performing 100J exposure in a voltage-off state, a polymer stabilized vertical alignment (PS-VA) liquid crystal display device was obtained.
As for the PS-VA liquid crystal display devices using the liquid crystal compositions containing the polymerizable compounds of examples 9 to 14, similar results to those of the VA liquid crystal display devices using the liquid crystal compositions of examples 1 to 3 were obtained by measuring the driving voltage, the low-temperature storage stability and the transmittance.
Next, the amount of the polymerizable compound remaining in the liquid crystal display devices obtained in examples 9 to 14 was confirmed, and as a result, the remaining amount was sufficiently small. It was thus confirmed that a PS-VA liquid crystal display device in which display failure due to a change in the pretilt angle is less likely to occur.
As described above, it was confirmed that the liquid crystal composition of the present invention can achieve both high-speed response, low driving voltage, good low-temperature storage stability, and high transmittance when used in a VA liquid crystal display device and a PS-VA display device.
Although the present invention is not exhaustive of all liquid crystal mixtures claimed, it is anticipated by those skilled in the art that other liquid crystal materials of the same type can be obtained in a similar manner without creative efforts based on the disclosed embodiments, only by combining with their own professional efforts. And are merely representative of embodiments, given the limited space available.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (14)
1. A negative dielectric anisotropy liquid crystal composition, comprising:
at least one compound represented by formula I; and the number of the first and second groups,
at least one compound represented by formula II;
in the formula I, R1、R2Each independently represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a linear alkenyl group having 2 to 8 carbon atoms, or a linear alkenyloxy group having 2 to 8 carbon atoms, wherein one or two of them are independently presentnon-adjacent-CH2-optionally substituted by-O-, wherein any H is optionally substituted by a F atom;
Z1、Z2each independently represents-C2H2-、-C2H4-、-C2H2CH2O-、-OCH2C2H2-、-CH2O-、-OCH2-、-C2H2CH2S-、-SCH2C2H2-、-CH2S-、-SCH2-、-O-、-S-、-CF2O-、-OCF2-, -C.ident.C-, -OOC-or-COO-, in which-CH2O-、-C2H2-、-C2H4-、-C2H2CH2O-, or-OCH2C2H2Any H in-is optionally substituted with F;
x represents-O-, -S-, -SO-, -SOO-, -CF2-, -CO-or-CH2-；
Y1、Y2Each independently represents-F-, -OCH2F-、-OCHF2-or-OCF3-, in which Y1、Y2Does not simultaneously represent-F-;
n represents 0, 1, 2 or 3;
in the formula II, R3、R4Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms; and, R3、R4Each independently of the other, H on any carbon atom in (a) is optionally substituted with F;
p represents 0, 1 or 2.
2. The negative dielectric anisotropic liquid crystal composition of claim 1, wherein the compound of formula I is selected from the group consisting of compounds of formulae IA to IZK and Ia to Izk, wherein R is1、R2The definitions are the same as in claim 1,
3. the negative dielectric anisotropic liquid crystal composition of claim 2, wherein the compound represented by formula I is selected from the group consisting of compounds represented by formulae IA-1 to IZK-4 and formulae Ia-1 to Izk-4, wherein Alkyl represents a linear Alkyl group having C1 to C8, and alkinyl represents a linear Alkenyl group having C2 to C8,
4. the negative dielectric anisotropic liquid crystal composition of any one of claims 1 to 3, wherein the compound represented by formula II is selected from the group consisting of the following compounds represented by formulae II-1 to II-10:
R3、R4each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms; r3、R4Each hydrogen on any carbon atom in (a) is independently optionally substituted with fluorine;
(F) represents F or H.
5. The negative dielectric anisotropic liquid crystal composition of any one of claims 1 to 4, wherein the liquid crystal composition further comprises one or more compounds represented by formula III below:
R5、R6each is independentThe alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 5 carbon atoms, the alkenyl group having 2 to 5 carbon atoms, or the alkenyloxy group having 2 to 5 carbon atoms; and, R5、R6Each independently of the other, H on any carbon atom in (a) is optionally substituted with F;
Z3represents a single bond or-CH2O-；
q and r each independently represent 0, 1 or 2;
6. the negative dielectric anisotropic composition of claim 5, wherein the compound represented by formula iii is selected from the group consisting of compounds represented by formulae iii-1 to iii-17 below:
R5、R6each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms, and R5、R6Each independently of the other, is optionally substituted with F.
7. The negative dielectric anisotropic liquid crystal composition of any one of claims 1 to 6, wherein the liquid crystal composition further comprises one or more compounds represented by formulae IV-1 to IV-50 below:
wherein R is1' represents H or an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and optionally 4 or less of H are substituted by F;
R2' represents H or alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two non-adjacent-CH2-is optionally substituted by-O-, and optionally 4 or fewer H are substituted by F.
8. The negative dielectric anisotropic liquid crystal composition of any one of claims 1 to 7, wherein the liquid crystal composition further comprises one or more compounds represented by the following formulas V-1 to V-8:
9. the negative dielectric anisotropic liquid crystal composition according to claim 5 or 6, wherein the amount of the compound represented by formula I is 1 to 50 parts by mass, the amount of the compound represented by formula II is 1 to 60 parts by mass, and the amount of the compound represented by formula III is 1 to 50 parts by mass, based on 100 parts by mass of the negative dielectric anisotropic liquid crystal composition.
10. The negative dielectric anisotropic liquid crystal composition of claim 7, wherein the amount of the compound represented by formula I is 1 to 50 parts by mass, the amount of the compound represented by formula II is 1 to 60 parts by mass, the amount of the compound represented by formula III is 1 to 50 parts by mass, and the amount of the compound represented by formula IV is 1 to 40 parts by mass, based on 100 parts by mass of the negative dielectric anisotropic liquid crystal composition.
11. The negative dielectric anisotropic liquid crystal composition of claim 8, wherein the amount of the compound represented by formula I is 1 to 50 parts by mass, the amount of the compound represented by formula II is 1 to 60 parts by mass, the amount of the compound represented by formula III is 1 to 50 parts by mass, the amount of the compound represented by formula IV is 1 to 40 parts by mass, and the amount of the compound represented by formula V is 0.01 to 1.00 part by mass, based on 100 parts by mass of the negative dielectric anisotropic liquid crystal composition.
12. The negative dielectric anisotropy liquid crystal composition according to any one of claims 1 to 11, further comprising an additive selected from at least one of a UV stabilizer, an antioxidant, a chiral dopant, and a polymerization initiator, the additive being added in an amount of 0.01% to 1.5% of the total mass of the liquid crystal composition.
13. A liquid crystal display device, wherein the liquid crystal composition comprises the liquid crystal composition according to any one of claims 1 to 12; the liquid crystal display device is an active matrix display device or a passive matrix display device.
14. The liquid crystal display device of claim 13, wherein the liquid crystal display device is driven in a PS-VA mode, a VA mode, an IPS mode, an FFS mode, a PS-IPS mode, a PS-FFS mode, or an ECB mode.
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