WO2016056455A1

WO2016056455A1 - Liquid crystal composition and liquid crystal display element using same

Info

Publication number: WO2016056455A1
Application number: PCT/JP2015/077919
Authority: WO
Inventors: 小川　真治; 栗山　毅; 芳典岩下
Original assignee: Dic株式会社
Priority date: 2014-10-10
Filing date: 2015-10-01
Publication date: 2016-04-14
Also published as: JP6132122B2; JPWO2016056455A1; CN106795434A

Abstract

　The present invention pertains to a nematic liquid crystal composition useful as a liquid crystal display material and having a negative dielectric constant anisotropy, and a liquid crystal display element using the same. The liquid crystal composition according to the present invention has a large absolute value for dielectric constant anisotropy and low viscosity, good solubility at lo temperatures, high specific resistance and voltage retention rate, and stable with respect to heat and light, and the liquid crystal display element using the same has excellent display quality with high contrast and fast responsiveness, but without burn-in or other display defects. The liquid crystal display element using the liquid crystal composition according to the present invention is useful for achieving fast responsiveness while also suppressing display defects, is particularly useful as a liquid crystal display element for active matrix driving, and can be applied as a VA, PSA, or other type of liquid crystal display element.

Description

Liquid crystal composition and liquid crystal display device using the same

The present invention relates to a liquid crystal composition having a negative dielectric anisotropy (Δε) useful as a liquid crystal display material and a liquid crystal display device using the same.

Liquid crystal display elements are used in various measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, etc., including clocks and calculators. Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, VA (vertical alignment) type using TFT (thin film transistor), and IPS (in-plane Switching) type. The liquid crystal composition used in these liquid crystal display elements is stable against external factors such as moisture, air, heat, light, etc., and exhibits a liquid crystal phase in the widest possible temperature range centering on room temperature, and has low viscosity. And a low driving voltage is required. Furthermore, the liquid crystal composition has several to several tens of kinds of compounds in order to optimize the dielectric anisotropy (Δε) and the refractive index anisotropy (Δn) for each display element. It is composed of

In a vertical alignment type display, a liquid crystal composition having a negative Δε is used, and the display is required to have performance such as low voltage driving, high speed response, and a wide operating temperature range. As a performance of a liquid crystal composition required for producing a display, an absolute value of Δε is large, a viscosity (η) is small, and a high nematic phase-isotropic liquid phase transition temperature (T _ni ) is required. Yes. Further, from the setting of Δn × d, which is the product of Δn and the cell gap (d), it is necessary to adjust Δn of the liquid crystal composition to an appropriate range according to the cell gap. In addition, when applying a liquid crystal display element to a television or the like, since high-speed response is important, a liquid crystal composition having a small γ ₁ is required. In particular, in recent years, in order to reduce the cell gap in order to increase the response speed, it is necessary to increase Δn at the same time as reducing the viscosity. Therefore, a liquid crystal using a compound having a plurality of benzene rings. Compositions have been studied, and Patent Documents 1 and 2 have already disclosed liquid crystal compositions using a compound having a terphenyl structure substituted with fluorine.
On the other hand, the use of liquid crystal display elements has been expanded, and there has been a significant change in the method of use and manufacturing method. In order to cope with these changes, it has become necessary to optimize characteristics other than the basic physical property values as conventionally known. That is, liquid crystal display elements using a liquid crystal composition are widely used, such as VA type and IPS type, and super large size display elements having a size of 50 type or more are practically used. Became. As the substrate size is increased, the method of injecting the liquid crystal composition into the substrate has been changed from the conventional vacuum injection method to the drop injection (ODF: One Drop Fill) method, but the liquid crystal composition is applied to the substrate. The problem that the drop marks when dropped causes the display quality to deteriorate is brought to the surface.

Furthermore, in the liquid crystal display element manufacturing process by the ODF method, it is necessary to drop an optimal liquid crystal injection amount according to the size of the liquid crystal display element. When the deviation of the injection amount increases from the optimum value, the balance between the refractive index and the driving electric field of the liquid crystal display element designed in advance is lost, and display defects such as spots and contrast defects occur. In particular, small liquid crystal display elements that are frequently used in smartphones that have become popular recently are difficult to control the deviation from the optimum value within a certain range because the optimum liquid crystal injection amount is small. Therefore, in order to keep the yield of the liquid crystal display element high, for example, there is little influence on the sudden pressure change and impact in the dropping device that occurs when dropping the liquid crystal, and the ability to keep dropping the liquid crystal stably for a long time Is also necessary.

As described above, in a liquid crystal composition used for an active matrix drive liquid crystal display element driven by a TFT element or the like, a liquid crystal display is maintained while maintaining characteristics and performance required for a liquid crystal display element such as a high-speed response performance. In consideration of the manufacturing method of the element, in addition, it has a high specific resistance value or a high voltage holding ratio which has been emphasized conventionally, and is stable against external stimuli such as light and heat (Patent Documents 3 to 5) ) Has been required to develop further.

JP 2003-327965 A WO2007 / 077872 JP-A-9-124529 JP 2006-169472 A Patent No. 5170603

The problems to be solved by the present invention include a liquid crystal phase in a wide temperature range, low viscosity, good solubility at low temperatures, high specific resistance and high voltage holding ratio, and stability against heat and light. Provided is a liquid crystal composition having a negative Δε, which can produce a liquid crystal display element excellent in display quality, in which display defects such as image sticking and dripping marks are unlikely to occur, and using this liquid crystal composition Accordingly, an object of the present invention is to provide a liquid crystal display element such as a VA type or a PSVA type which is excellent in display quality and hardly causes display defects such as image sticking and dripping marks.

The present inventors have studied various liquid crystal compounds and various chemical substances, and found that the above problems can be solved by combining specific compounds, and have completed the present invention.
Formula (I)

(Wherein R ¹ represents a linear or branched alkyl group having 1 to 22 carbon atoms, and one or more CH ₂ groups in the alkyl group are not directly adjacent to an oxygen atom. May be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF ₂ O—, —OCF ₂ —, and X ₁ is — One or more compounds represented by CH ₂ — or an oxygen atom)),
Formula (L-1) to Formula (L-6)

(Wherein R ^L11 to R ^L62 each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one of which is an alkenyl group having 2 to 10 carbon atoms) X ^L61 and X ^L62 each independently represents a hydrogen atom or a fluorine atom, but at least one represents a hydrogen atom.) One or more compounds selected from the group consisting of compounds represented by A liquid crystal composition is provided, and a liquid crystal display element using the liquid crystal composition is provided.

The liquid crystal composition having a negative Δε according to the present invention has a liquid crystal phase in a wide temperature range, a viscosity much lower than that of the conventional one, good solubility at low temperatures, and its specific resistance and voltage holding ratio. The degree of change due to heat and light is extremely small, and particularly the change over a long period is small. For this reason, the liquid crystal composition of the present invention has high practical applicability to liquid crystal products, and liquid crystal display elements such as VA type, PSVA type and n type FFS type using the liquid crystal composition can achieve high-speed response. . In addition, since the liquid crystal composition of the present invention can stably exhibit its performance even after the manufacturing process of the liquid crystal display element, display defects due to the manufacturing process are suppressed, and the liquid crystal display element can be manufactured with a high yield. So it is very useful.

The composition of the present invention preferably exhibits a liquid crystal phase at room temperature (25 ° C.), and more preferably exhibits a nematic phase. The composition of the present invention contains a dielectrically nearly neutral compound (Δε value is −2 to 2) and a negative compound (Δε value is less than 2). The dielectric anisotropy of the compound is a value extrapolated from a measured value of the dielectric anisotropy of a composition prepared by adding to a dielectrically nearly neutral composition at 25 ° C. In addition, although content is described in% below, this means mass%. In the liquid crystal composition in the present invention, the general formula (I)

The compound represented by these is contained. Specifically, it is a compound represented by the following formulas (I-1) and (I-2).

R ¹ represents a straight-chain alkyl group or a branched-chain alkyl group having 1 to 22 carbon atoms, and one or two or more CH ₂ groups in the alkyl group are —O—so that oxygen atoms are not directly adjacent to each other. —, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF ₂ O—, —OCF ₂ — may be substituted. It is preferably a straight chain alkyl group, a branched chain alkyl group, or a straight chain alkoxy group having 1 to 10 carbon atoms.

In the liquid crystal composition of the present invention, the compound represented by the general formula (I) contains one or two compounds, preferably one to five compounds, more preferably at a low temperature. In consideration of characteristics such as solubility, transition temperature, electrical reliability, and birefringence, there are upper and lower limits for each embodiment.

The lower limit of the preferable content of the compound represented by the formula (I) with respect to the total amount of the liquid crystal composition of the present invention is 0.001%, 0.005%, and 0.01%. 0.02%. The upper limit of the preferable content is 0.1%, 0.08%, and 0.05%.
The content is preferably 0.001 to 1% by mass, more preferably 0.001 to 0.1% by mass, and particularly preferably 0.001 to 0.05% by mass.

The liquid crystal composition of the present invention contains one or more compounds selected from the group consisting of compounds represented by formulas (L-1) to (L-6).

R ^L11 to R ^L62 in the formula independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and at least one of them represents an alkenyl group having 2 to 10 carbon atoms. To express. X ^L61 and X ^L62 each independently represent a hydrogen atom or a fluorine atom, but at least one of them represents a hydrogen atom.

The compounds represented by the general formulas (L-1) to (L-6) are represented by the following general formulas (L-1-A) to (L-6-A), respectively. It is preferable that it is a compound.

In the formula, R ^L12A to R ^L62A each independently represent an alkyl group having 1 to 8 carbon atoms, R ^L11B to R ^L61B each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, n ^L11C to n ^L61C each independently represents an integer of 0 to 8, but R ^L12A to R ^L62A are preferably each independently an alkyl group having 1 to 5 carbon atoms, and ^11B to R ^L61B are It is preferably independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n ^L11C to n ^L61C each independently represents an integer of 0 to 4, and represents an integer of 0 or 2 Is more preferable.

Is more preferably a group represented by any one of formulas (R1) to (R5).

The compound represented by the general formula (L-1-A) is preferably a compound selected from the group of compounds represented by the general formula (L-1-1).

The lower limit of the preferable content of the compound represented by the formula (L-1-1) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5% %, 7%, and 10%. The upper limit of the preferable content is 30%, 25%, 20%, 15%, 13%, and 10% with respect to the total amount of the liquid crystal composition of the present invention. 8%, 7%, 6%, 5%, 3%.

The compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.1) to the formula (L-1-1.3). And is preferably a compound represented by formula (L-1-1.2) or formula (L-1-1.3), and particularly represented by formula (L-1-1.3). It is preferable that it is a compound.

The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3% 5%, 7%, and 10%. The upper limit of the preferable content is 30%, 25%, 20%, 15%, 13%, and 10% with respect to the total amount of the liquid crystal composition of the present invention. 8%, 7%, 6%, 5%, 3%.

The compound represented by the general formula (L-1-A) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).

The lower limit of the preferable content of the compound represented by the formula (L-1-2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 15 %, 17%, 20%, 23%, 25%, 27%, 30%, 35%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, and 40% with respect to the total amount of the liquid crystal composition of the present invention. 38%, 35%, 33%, 30%.

Further, the compound represented by the general formula (L-1-2) is a compound selected from the group of compounds represented by the formula (L-1-2.1) to the formula (L-1-2.4). Preferably, it is a compound represented by the formula (L-1-2.2) to the formula (L-1-2.4). In particular, the compound represented by the formula (L-1-2.2) is preferable because the response speed of the composition of the present invention is particularly improved. When obtaining Tni higher than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L-1-2.4). The content of the compounds represented by formula (L-1-2.3) and formula (L-1-2.4) is not preferably 30% or more in order to improve the solubility at low temperatures.

The lower limit of the preferable content of the compound represented by the formula (L-1-2.2) with respect to the total amount of the liquid crystal composition of the present invention is 10%, 15%, and 18%. , 20%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, and 40%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, and 40% with respect to the total amount of the liquid crystal composition of the present invention. 38%, 35%, 32%, 30%, 27%, 25%, 22%.

The total amount when the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) are used in combination with respect to the total amount of the liquid crystal composition of the present invention. The lower limit of the preferable content is 10%, 15%, 20%, 25%, 27%, 30%, 35%, and 40%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, and 22%.

The compound represented by the general formula (L-1-A) is preferably a compound selected from the group of compounds represented by the general formulas (L-1-4) and (L-1-5).

The lower limit of the preferable content of the compound represented by the formula (L-1-4) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 13 %, 15%, 17%, and 20%. The upper limit value of the preferable content is 25%, 23%, 20%, 17%, 15%, 13% with respect to the total amount of the liquid crystal composition of the present invention, 10%.

The lower limit of the preferable content of the compound represented by the formula (L-1-5) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 13 %, 15%, 17%, and 20%. The upper limit value of the preferable content is 25%, 23%, 20%, 17%, 15%, 13% with respect to the total amount of the liquid crystal composition of the present invention, 10%.

Furthermore, the compounds represented by the general formulas (L-1-4) and (L-1-5) are represented by the formulas (L-1-4.1) to (L-1-5.3). And a compound represented by the formula (L-1-4.2) or the formula (L-1-5.2) is preferable.

The lower limit of the preferable content of the compound represented by the formula (L-1-4.2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3% 5%, 7%, 10%, 13%, 15%, 18%, and 20%. The upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8% with respect to the total amount of the liquid crystal composition of the present invention, 7% and 6%.

Formula (L-1-1.3), Formula (L-1-2.2), Formula (L-1-3.1), Formula (L-1-3.3), Formula (L-1- 3.4), it is preferable to combine two or more compounds selected from the compounds represented by formula (L-1-3.11) and formula (L-1-3.12). -1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4) and It is preferable to combine two or more compounds selected from the compounds represented by formula (L-1-4.2), and the lower limit of the preferable content of the total content of these compounds is the liquid crystal composition of the present invention. 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, and 18% of the total amount of goods Yes, 20%, 23% 25%, 27%, 30%, 33%, and 35%. The upper limit is 80% with respect to the total amount of the liquid crystal composition of the present invention, and 70%. 60%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 28%, 25% 23% and 20%. When emphasizing the reliability of the composition, compounds represented by formula (L-1-3.1), formula (L-1-3.3) and formula (L-1-3.4)) It is preferable to combine two or more compounds selected from the group consisting of formulas (L-1-1.3) and (L-1-2.2) when the response speed of the composition is important. It is preferable to combine two or more compounds selected from the following compounds.

The compound represented by the general formula (L-2-A) is preferably a compound selected from the group of compounds represented by the formula (L-2.7) to the formula (L-2.12).

The lower limit of the preferable content of the compound represented by the general formula (L-2-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition of the present invention, 6%, 5%, 3%.

The compound represented by the general formula (L-3-A) is preferably a compound selected from the group of compounds represented by the formula (L-3.8) to the formula (L-3.13).

The lower limit of the preferable content of the compound represented by the formula (L-3-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5% %, 7%, and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition of the present invention, 6%, 5%, 3%.

The compound represented by the general formula (L-4-A) is preferably a compound represented by the formula (L-4.1) to the formula (L-4.3).

The lower limit of the preferable content of the compound represented by the general formula (L-4-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. The upper limit of the preferable content of the compound represented by the formula (L-4) with respect to the total amount of the liquid crystal composition of the present invention is 50%, 40%, 35%, and 30%. Yes, 20%, 15%, 10%, 5%.

A preferable combination of the compounds represented by the general formula (L-4-A) is, for example, according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. Whether it contains a compound represented by L-4.1) or a compound represented by formula (L-4.2), it is represented by formula (L-4.1). Both the compound and the compound represented by (L-4.2) may be contained, or all the compounds represented by formula (L-4.1) to formula (L-4.3) It may be included. The lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) with respect to the total amount of the liquid crystal composition of the present invention is 3%, and 5% 7%, 9%, 11%, 12%, 13%, 18%, 21%, and a preferred upper limit is 45, 40%. Yes, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% is there.

When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, both compounds relative to the total amount of the liquid crystal composition of the present invention The lower limit of the preferable content of 15%, 19%, 24%, and 30%, and the preferable upper limit is 45%, 40%, 35%, and 30%. %, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (L-5-A) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2).

The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10% 14%, 16%, 20%, 23%, 26%, 30%, 35%, and 40%. The upper limit of the preferable content of these compounds is 50%, 40%, 35%, 30%, 20%, 15%, 10%, and 5%. .

The compound represented by the general formula (L-6-A) is preferably a compound represented by the formula (L-6.10) to the formula (L-6.17).

The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, and 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.

The liquid crystal composition of the present invention contains one or more compounds selected from the group consisting of compounds represented by general formula (L-1) to general formula (L-6). 1) The compound represented by formula (L-1) and the compound represented by formula (L-2) are preferably contained, and the compound represented by formula (L-1) and formula The compound represented by (L-3) is preferably contained, and the compound represented by formulas (L-1) and (L-4) is preferably contained, represented by formula (L-1). ) And a compound represented by the general formula (L-5) are preferably contained, and a compound represented by the general formula (L-1) and the general formula (L-6) is preferably contained.

The liquid crystal composition of the present invention has the general formula (N-1)

(Wherein, R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, and n ^N11 and n ^N12 are 0 or 1 And n ^N11 + n ^N12 represents 0 or 1.)
It is preferable to contain 1 type, or 2 or more types of compounds represented by these. The compound represented by the general formula (N-1) has two or more benzene rings, and has two fluorine groups in the benzene ring. These compounds have the property that the dielectric anisotropy (Δε) is negative and Δn is large.

The compound represented by the general formula (N-1) is preferably a compound having an absolute value of Δε larger than 3.

In general formula (N-1), R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or An alkenyloxy group having 2 to 8 carbon atoms is preferable, 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 alkyl group having 2 to 5 carbon atoms. An alkenyloxy group is preferred, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferred, and an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferred. An alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.

Further, when the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which it is bonded is cyclohexane, a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms And straight-chain alkenyl groups having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)

The lower limit of the preferable content of the compound represented by the formula (N-1) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

As the compound represented by the general formula (N-1), a compound represented by the general formula (N-1-3) is preferable.

( ^Wherein , R ^N131 and R ^N132 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-3) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

It is preferable to set a higher content in the case of emphasizing improved [Delta] [epsilon], to emphasize the solubility at low temperature highly effective when larger amount to set the content, when importance is attached to T _NI content Highly effective when set to. Furthermore, when improving dripping marks and image sticking characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-1-3) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

Further, the compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.11). Preferably, it is a compound represented by the formulas (N-1-3.1) to (N-1-3.7), and the formula (N-1-3.1) and the formula (N -1-3.2), formula (N-1-3.3), formula (N-1-3.4) and compounds represented by formula (N-1-3.6) are preferred.

The compounds represented by formula (N-1-3.1) to formula (N-1-3.4) and formula (N-1-3.6) may be used alone or in combination. Is possible, but the combination of formula (N-1-3.1) and formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) ) And a combination of two or three selected from formula (N-1-3.6) are preferred. The lower limit of the preferred content of these compounds alone or with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20% %. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

As the compound represented by the general formula (N-1), a compound represented by the general formula (N-1-4) is also preferable.

^{(Wherein, R N141} and ^{R N142} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
R ^N141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. ^RN142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-4) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

It is preferable to set a higher content in the case of emphasizing improved [Delta] [epsilon], to emphasize the solubility at low temperature highly effective when larger amount to set the content, when importance is attached to T _NI content Setting to a small value is highly effective. Furthermore, when improving dripping marks and image sticking characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-1-4) with respect to the total amount of the liquid crystal composition of the present invention is 3%, 5%, 7%, 10% %, 13%, 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15%, 13%, 11%, 10%, 8%.

Further, the compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formula (N-1-4.1) to the formula (N-1-4.14). Preferably, it is a compound represented by the formulas (N-1-4.1) to (N-1-4.4), and the formula (N-1-4.1) and the formula (N The compound represented by -1-4.2) is preferable.

The compounds represented by the formulas (N-1-4.1) to (N-1-4.4) can be used alone or in combination, but the liquid crystal composition of the present invention The lower limit of the preferred content of these compounds alone or with respect to the total amount of is 3%, 5%, 7%, 10%, 13%, 15%, 17 % And 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15%, 13%, 11%, 10%, 8%.

As the compound represented by the general formula (N-1), a compound represented by the general formula (N-1-5) is also preferable.

(In the formula, R ^N151 and R ^N152 each independently represent the same meaning as R ^N11 and R ^N12 in General Formula (N).)
R ^N151 and R ^N152 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, butenyl group, ethyl group, propyl Group or butyl group is preferred.

The compound represented by the general formula (N-1-5) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

When emphasizing the improvement of Δε, it is preferable to set the content higher. When emphasizing the solubility at low temperature, it is more effective to set the content lower. When emphasizing T _NI , the content is preferable. Setting a large number of is highly effective. Furthermore, when improving dripping marks and image sticking characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-1-5) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 8%, 10%, 13 %, 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, and 23% with respect to the total amount of the liquid crystal composition of the present invention, 20%, 18%, 15%, 13%.

Further, the compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formula (N-1-5.1) to the formula (N-1-5.6). The compound represented by the formula (N-1-3.2 and the formula (N-1-3.4) is preferable.

The compounds represented by formula (N-1-5.2) and formula (N-1-5.4) can be used alone or in combination, but the liquid crystal composition of the present invention The lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 8%, 10%, 13%, 15%, 17%, 20%. The upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, and 23% with respect to the total amount of the liquid crystal composition of the present invention, 20%, 18%, 15%, 13%.

The liquid crystal composition of the present invention has the general formula (N-4)

(Wherein R ⁴¹ and R ⁴² each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, X ⁴¹ is a single bond, —CH ₂ CH ₂ — or —CH ₂ O—, and n ^N41 represents 0 or 1).

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-1) is preferable.

(In the formula, R ^N111 and R ^N112 each independently represent the same meaning as R ^N41 and R ^N42 in formula (N-4).)
R ^N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group. ^RN112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.

The compound represented by the general formula (N-4-1) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-1) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.

Further, the compound represented by the general formula (N-4-1) is a compound selected from the group of compounds represented by the formula (N-4-1.1) to the formula (N-4-1.14). Preferably, it is a compound represented by the formulas (N-4-1.1) to (N-4-1.4), and the formula (N-4-1.1) and the formula (N The compound represented by -4-1.3) is preferred.

The compounds represented by the formulas (N-4-1.1) to (N-4-1.4) can be used alone or in combination, but the liquid crystal composition of the present invention The lower limit of the preferable content of these compounds alone or with respect to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%, 23 %, 25%, 27%, 30%, 33%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-2) is preferable.

(Wherein, R ^N121 and R ^N122 each independently represent the same meaning as R ^N41 and R ^N42 in formula (N-4)).
^RN121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group or a pentyl group. ^RN122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and includes a methyl group, a propyl group, a methoxy group, an ethoxy group, or a propoxy group. preferable.

The compound represented by the general formula (N-4-2) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-2) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 7%, 10%, 13 %, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37 %, 40%, and 42%. The upper limit of the preferred content is 50%, 48%, 45%, 43%, 40%, 38%, with respect to the total amount of the liquid crystal composition of the present invention, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%.

Further, the compound represented by the general formula (N-4-2) is a compound selected from the group of compounds represented by the formula (N-4-2.1) to the formula (N-4-2.13). Preferably, the formula (N-4-2.3) to the formula (N-4-2.7), the formula (N-4-2.10), the formula (N-4-2.11) and the formula A compound represented by (N-4-2.13) is preferable, and when importance is placed on the improvement of Δε, the formula (N-4-2.3) to the formula (N-4-2.7) In the case where improvement of T _NI is important, the compound represented by formula (N-4-2.10), formula (N-4-2.11) and formula (N-4-2.13) It is preferable that it is a compound represented by these.

The compounds represented by the formulas (N-4-2.1) to (N-4-2.13) can be used alone or in combination. The lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-10) is preferable.

(In the formula, R ^N1101 and R ^N1102 each independently represent the same meaning as R ^N41 and R ^N42 in formula (N-4).)
R ^N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propenyl group, an ethyl group, a propyl group, or a butyl group. R ^N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-4-10) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-10) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

Further, the compound represented by the general formula (N-4-10) is a compound selected from the group of compounds represented by the formula (N-4-100.1) to the formula (N-4-10.15). Preferably, it is a compound represented by the formulas (N-4-10.1) to (N-4-10.5), and the formula (N-4-10.1) and the formula (N The compound represented by −4-10.2) is preferable.

The compounds represented by the formulas (N-4-10.1) and (N-4-10.2) can be used alone or in combination. The lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-11) is preferable.

(In the formula, R ^N1111 and R ^N1112 each independently represent the same meaning as R ^N41 and R ^N42 in formula (N-4).)
R ^N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propenyl group, an ethyl group, a propyl group, or a butyl group. R ^N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-4-11) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-11) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

Further, the compound represented by the general formula (N-4-11) is a compound selected from the group of compounds represented by the formula (N-4-11.1) to the formula (N-4-11.15). It is preferably a compound represented by the formulas (N-4-11.1) to (N-4-11.15), and the compounds represented by the formulas (N-4-11.2 and the formula (N- The compound represented by 4-11.4) is preferable.

The compounds represented by the formula (N-4-11.2) and the formula (N-4-11.4) can be used alone or in combination. The lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-12) is preferable.

(In the formula, R ^N1121 and R ^N1122 each independently represent the same meaning as R ^N41 and R ^N42 in Formula (N-4).)
^RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. ^RN1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-4-12) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-12) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

As the compound represented by the general formula (N-4), a compound represented by the general formula (N-4-13) is preferable.

( ^Wherein , R ^N1131 and R ^N1132 each independently represent the same meaning as R ^N41 and R ^N42 in formula (N-4)).
R ^N1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-4-13) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-4-13) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.

The liquid crystal composition of the present invention may contain one or more compounds selected from the compounds represented by the general formulas (N-2) and (N-3).

(Wherein R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH _{2 in the} alkyl group Each — may be independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^N21 , A ^N22 , A ^N31 and A ^N32 each independently represent (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more non-adjacent — CH ₂ — may be replaced by —O—) and (b) a 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ not adjacent to each other). May be replaced by -N =.)
(C) (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6- One —CH═ present in a diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH═ are replaced by —N═. Is also good.)
The group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 are each independently a single bond —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO. -, -OCF _2- , -CF ₂ O-, -CH = NN-CH-, -CH = CH-, -CF = CF- or -C≡C-
^XN21 represents a hydrogen atom or a fluorine atom,
T ^N31 represents —CH ₂ — or an oxygen atom,
n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, while n ^N21 + n ^N22 and n ^N31 + n ^N32 are each independently 1, 2 or 3, and A ^N21 to When a plurality of A ^N32 and Z ^N21 to Z ^N32 are present, they may be the same or different. )
The compounds represented by the general formulas (N-2) and (N-3) are preferably compounds having a negative Δε and an absolute value larger than 3.

In the general formulas (N-2) and (N-3), R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. Group, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 2 to 2 carbon atoms. 5 alkenyl groups or alkenyloxy groups having 2 to 5 carbon atoms are preferable, alkyl groups having 1 to 5 carbon atoms or alkenyl groups having 2 to 5 carbon atoms are more preferable, and alkyl groups having 2 to 5 carbon atoms. Alternatively, an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.

Further, when the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a straight chain A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

A ^N21 , A ^N22 , A ^N31 and A ^N32 are preferably aromatic when it is required to independently increase Δn, and are preferably aliphatic for improving the response speed. Trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4 -Phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, It preferably represents a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and has the following structure: Succoth, more preferably,

More preferably, it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

^{^Z ^N21,} Z N22, Z ^N31 and ^{Z N32} is _-CH 2 O _{independently} _{-, - CF 2 O -,} - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _{_{-CH 2 O -, - CH 2}} CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

^XN21 is preferably a fluorine atom.

T ^N31 is preferably an oxygen atom.

n ^N21 + n ^N22 and n ^N31 + n ^N32 are preferably 1 or 2, a combination in which n ^N21 is 1 and n ^N22 is 0, a combination in which n ^N21 is 2 and n ^N22 is 0, and n ^N31 is 1 A combination in which n ^N32 is 0 and a combination in which n ^N31 is 2 and n ^N32 is 0 are preferable.

The lower limit of the preferable content of the compound represented by the formula (N-2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

The lower limit of the preferable content of the compound represented by the formula (N-3) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

When the liquid crystal composition of the present invention maintains a low viscosity and a composition having a high response speed is required, the above lower limit value is preferably low and the upper limit value is preferably low. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, the above lower limit value is preferably low and the upper limit value is preferably low. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above lower limit value is increased and the upper limit value is high.

The compound represented by the general formula (N-2) is preferably a compound selected from the group of compounds represented by the general formulas (N-2-1) to (N-2-3).

The compound represented by the general formula (N-2-1) is the following compound.

^{(Wherein, R N211} and ^{R N212} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
The compound represented by the general formula (N-2-2) is the following compound.

^{(Wherein, R N221} and ^{R N222} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
The compound represented by the general formula (N-2-3) is the following compound.

^{(Wherein, R N231} and ^{R N232} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formulas (N-3-1) to (N-3-2).

The compound represented by the general formula (N-3-1) is the following compound.

(In the formula, R ^N311 and R ^N312 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
The compound represented by the general formula (N-3-2) is the following compound.

(In the formula, R ^N321 and R ^N322 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
In the liquid crystal composition of the present invention, examples of other components include compounds represented by general formula (L-2-B).

(In the formula, R ^L21 and R ^L22 each independently represent the same meaning as R ^L21 and R ^L22 in formula (L-2).)
R ^L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L22 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 4 to 5 carbon atoms.

Further, the compound represented by the general formula (L-2-B) is preferably a compound selected from the group of compounds represented by the formula (L-2.3) to the formula (L-2.6). The compounds represented by formula (L-2.3) and formula (L-2.4) are preferable.

In the liquid crystal composition of the present invention, examples of other components include compounds represented by general formula (L-7).

(Wherein, R ^L71 and R ^L72 each independently represent the same meaning as R ^L11 and R ^L12 in formula (L-1);
A ^L71 and ^{A L72} each independently (7a) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - is -O And (7b) 1,4-phenylene group (one —CH═ present in this group or two or more non-adjacent —CH═s replaced with —N =) May be.)
(7c) (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6- One —CH═ present in a diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH═ are replaced by —N═. Is also good.)
Each of the groups (7a), (7b) and (7c) is independently selected from the group consisting of: a hydrogen atom substituted with a cyano group, a fluorine atom or a chlorine atom. well,
Z ^L71 represents a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —OCF ₂ —, —CF ₂ O—. -CH = NN-CH-, -CH = CH-, -CF = CF- or -C≡C-
X ^L71 and X ^L72 each independently represent a fluorine atom or a hydrogen atom, but at least one of them represents a hydrogen atom. )
In the formula, R ^L71 and R ^L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and A ^L71 and A ^L72 are each independently 1,4-cyclohexyl. A silene group or a 1,4-phenylene group is preferable, and hydrogen atoms on A ^L71 and A ^L72 may be each independently substituted with a fluorine atom, and Z ^L71 is preferably a single bond or COO— X ^L71 and X ^L72 are preferably hydrogen atoms.

There are no particular restrictions on the types of compounds that can be combined, but they are combined according to the required performance, such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, and four kinds.

In the composition of the present invention, the content of the compound represented by the general formula (L-7) includes solubility at low temperature, transition temperature, electrical reliability, birefringence index, process suitability, dripping marks, It is necessary to adjust appropriately according to required performance such as image sticking and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5% Yes, 7%, 10%, 14%, 16%, 20%. The upper limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the liquid crystal composition of the present invention is 30%, 25%, 23%, 20% Yes, 18%, 15%, 10%, 5%.

When a high Tni embodiment of the liquid crystal composition of the present invention is desired, it is preferable to increase the content of the compound represented by formula (L-7), and when a low viscosity embodiment is desired, It is preferable to reduce the amount.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.1) to the formula (L-7.4), and the formula (L-7. It is preferable that it is a compound represented by 2).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.11) to the formula (L-7.13). It is preferable that it is a compound represented by 11).

Furthermore, the compound represented by the general formula (L-7) is a compound represented by the formula (L-7.21) to the formula (L-7.23). A compound represented by formula (L-7.21) is preferable.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.31) to the formula (L-7.34), and the formula (L-7. 31) or / and a compound represented by the formula (L-7.32).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.41) to the formula (L-7.44), and the formula (L-7. 41) or / and a compound represented by formula (L-7.42).

The liquid crystal composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms such as a peracid (—CO—OO—) structure are bonded in the molecule.

When emphasizing the reliability and long-term stability of the liquid crystal composition, the content of the compound having a carbonyl group is preferably 5% or less, and preferably 3% or less with respect to the total mass of the liquid crystal composition. Is more preferably 1% or less, and most preferably not substantially contained.

When importance is attached to stability by UV irradiation, the content of the compound substituted with chlorine atoms is preferably 15% or less, preferably 10% or less, based on the total mass of the liquid crystal composition, It is preferably 8% or less, more preferably 5% or less, further preferably 3% or less, and still more preferably substantially not contained.

It is preferable to increase the content of a compound in which all the ring structures in the molecule are 6-membered rings, and the content of the compound in which all the ring structures in the molecule are 6-membered rings is based on the total mass of the liquid crystal composition. It is preferably 80% or more, more preferably 90% or more, still more preferably 95% or more, and the composition is composed of only a compound in which all of the ring structures in the molecule are 6-membered rings. Most preferably, it is configured.

In order to suppress deterioration due to oxidation of the composition, it is preferable to reduce the content of the compound having a cyclohexenylene group as a ring structure, and the content of the compound having a cyclohexenylene group is the total mass of the liquid crystal composition. The content is preferably 10% or less, more preferably 8% or less, more preferably 5% or less, further preferably 3% or less, and still more preferably not contained.

When importance is attached to improvement of viscosity and improvement of Tni, the content of a compound having a 2-methylbenzene-1,4-diyl group in the molecule, in which a hydrogen atom may be substituted with a halogen, may be reduced. Preferably, the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% or less, more preferably 8% or less with respect to the total mass of the liquid crystal composition. It is preferably 5% or less, more preferably 3% or less, and still more preferably substantially not contained.

‘Substantially not contained’ in the present invention means that it is not contained except for unintentionally contained matter.

The composition of the present invention may contain a polymerizable compound in order to produce a liquid crystal display element such as a PS mode, a transverse electric field type PSA mode, or a transverse electric field type PSVA mode. Examples of the polymerizable compound that can be used include a photopolymerizable monomer that undergoes polymerization by energy rays such as light. The structure has, for example, a liquid crystal skeleton in which a plurality of six-membered rings such as biphenyl derivatives and terphenyl derivatives are connected. Examples thereof include a polymerizable compound. More specifically, the general formula (XX)

(Wherein, X ²⁰¹ and X ²⁰² each independently represent a hydrogen atom or a methyl group,
Sp ²⁰¹ and Sp ²⁰² each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH ₂ ) _s — (wherein _s represents an integer of 2 to 7, Preferably bonded to an aromatic ring)
Z ²⁰¹ represents —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CF ₂ CF ₂ —, —CH═ CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ₂ CH ₂ —, —OCO—CH ₂ CH ₂ —, —CH ₂ CH ₂ —COO—, —CH ₂ CH ₂ —OCO—, —COO—CH ₂ —, —OCO—CH ₂ —, —CH ₂ —COO—, —CH ₂ —OCO—, —CY ¹ ═CY ² — (Wherein Y ¹ and Y ² each independently represents a fluorine atom or a hydrogen atom), —C≡C— or a single bond;
M ²⁰¹ represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group or a single bond, and all 1,4-phenylene groups in the formula may have any hydrogen atom substituted by a fluorine atom. good. ) Is preferred.

X ²⁰¹ and X ²⁰² are each preferably a diacrylate derivative that represents a hydrogen atom, or a dimethacrylate derivative that has a methyl group, and a compound in which one represents a hydrogen atom and the other represents a methyl group. The polymerization rate of these compounds is the fastest for diacrylate derivatives, slow for dimethacrylate derivatives, and intermediate for asymmetric compounds, and a preferred embodiment can be used depending on the application. In the PSA display element, a dimethacrylate derivative is particularly preferable.

Sp ²⁰¹ and Sp ²⁰² each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH ₂ ) _s —, but at least one of them is a single bond in a PSA display element. A compound in which both represent a single bond or one in which one represents a single bond and the other represents an alkylene group having 1 to 8 carbon atoms or —O— (CH ₂ ) _s — is preferable. In this case, 1 to 4 alkyl groups are preferable, and s is preferably 1 to 4.

Z ²⁰¹ represents —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CF ₂ CF ₂ — or a single bond Are preferred, —COO—, —OCO— or a single bond is more preferred, and a single bond is particularly preferred.

M ²⁰¹ represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group or a single bond in which any hydrogen atom may be substituted by a fluorine atom, but the 1,4-phenylene group or the single bond is preferable. When C represents a ring structure other than a single bond, Z ²⁰¹ is preferably a linking group other than a single bond. When M ²⁰¹ is a single bond, Z ²⁰¹ is preferably a single bond.

From these points, in general formula (XX), the ring structure between Sp ²⁰¹ and Sp ²⁰² is specifically preferably the structure described below.

In the general formula (XX), when M ²⁰¹ represents a single bond and the ring structure is formed of two rings, the following formulas (XXa-1) to (XXa-5) are preferably represented, It is more preferable to represent the formula (XXa-3) from (XXa-1), and it is particularly preferable to represent the formula (XXa-1).

(In the formula, both ends shall be bonded to Sp ²⁰¹ or Sp ^202. )
The polymerizable compounds containing these skeletons are optimal for PSA-type liquid crystal display elements because of their alignment restriction power after polymerization, and a good alignment state is obtained, so that display unevenness is suppressed or does not occur at all.

From the above, as the polymerizable monomer, general formula (XX-1) to general formula (XX-4) are particularly preferable, and among them, general formula (XX-2) is most preferable.

(In the formula, Sp ²⁰ represents an alkylene group having 2 to 5 carbon atoms.)
In the case of adding a monomer to the composition of the present invention, the polymerization proceeds even when no polymerization initiator is present, but may contain a polymerization initiator in order to accelerate the polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.

The composition in the present invention may further contain a compound represented by the general formula (Q) together with the compound of the general formula (I).

(Wherein, R ^Q represents a straight-chain alkyl group or branched alkyl group having from 1 22 carbon atoms, one or two or more CH ₂ groups in the alkyl group, so that the oxygen atoms are not directly adjacent a, -O -, - CH = CH -, - CO -, - OCO -, - COO -, - C≡C -, - CF 2 O -, - OCF 2 - may be replaced by, ^{M Q} is trans Represents a 1,4-cyclohexylene group, a 1,4-phenylene group or a single bond.)
^RQ represents a straight-chain alkyl group or a branched-chain alkyl group having 1 to 22 carbon atoms, and one or more CH ₂ groups in the alkyl group are —O—so that oxygen atoms are not directly adjacent to each other. —, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF ₂ O—, —OCF ₂ — may be substituted. Linear alkyl group, linear alkoxy group, linear alkyl group in which one CH ₂ group is substituted with —OCO— or —COO—, branched alkyl group, branched alkoxy group, one CH ₂ group is —OCO— Or a branched alkyl group substituted with —COO—, a linear alkyl group having 1 to 20 carbon atoms, a linear alkyl group in which one CH ₂ group is substituted with —OCO— or —COO—, branched Chain alkyl group, branched alkoxy group, one CH ₂ group Is more preferably a branched alkyl group substituted with —OCO— or —COO—. ^MQ represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a single bond, and a trans-1,4-cyclohexylene group or a 1,4-phenylene group is preferred.

More specifically, the compound represented by the general formula (Q) is preferably a compound represented by the following general formula (Qa) to general formula (Qd).

In the formula, R ^Q1 is preferably a linear or branched alkyl group having 1 to 10 carbon atoms, R ^Q2 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, and R ^Q3 is A straight-chain alkyl group having 1 to 8 carbon atoms, a branched-chain alkyl group, a straight-chain alkoxy group or a branched-chain alkoxy group is preferred, and L ^Q is preferably a straight-chain alkylene group or branched-chain alkylene group having 1 to 8 carbon atoms. . Of the compounds represented by general formula (Qa) to general formula (Qd), compounds represented by general formula (Qc) and general formula (Qd) are more preferable.

In the liquid crystal composition of the present invention, when the compound represented by the general formula (Q) is contained, it is preferably contained in 1 to 5 types, and the content is preferably 0.001 to 1%, 0.001 to 0.1% is more preferable, and 0.001 to 0.05% is particularly preferable.

In the composition containing the polymerizable compound of the present invention, the polymerizable compound contained therein is polymerized by ultraviolet irradiation to impart liquid crystal alignment ability, and the amount of transmitted light is controlled using the birefringence of the composition. Used for liquid crystal display elements. As liquid crystal display elements, AM-LCD (active matrix liquid crystal display element), TN (nematic liquid crystal display element), STN-LCD (super twisted nematic liquid crystal display element), OCB-LCD and IPS-LCD (in-plane switching liquid crystal display element) However, it is particularly useful for AM-LCDs and can be used for transmissive or reflective liquid crystal display elements.

The two substrates of the liquid crystal cell used in the liquid crystal display element can be made of a transparent material having flexibility such as glass or plastic, and one of them can be an opaque material such as silicon. A transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.

The color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method. A method for producing a color filter by a pigment dispersion method will be described as an example. A curable coloring composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this process for each of the three colors red, green, and blue, a pixel portion for a color filter can be created. In addition, a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.

The substrate is opposed so that the transparent electrode layer is on the inside. In that case, you may adjust the space | interval of a board | substrate through a spacer. In this case, it is preferable to adjust so that the thickness of the obtained light control layer is 1 to 100 μm. More preferably, the thickness is 1.5 to 10 μm. When a polarizing plate is used, it is preferable to adjust the product of the refractive index anisotropy Δn of the liquid crystal and the cell thickness d so that the contrast is maximized. In addition, when there are two polarizing plates, the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good. Furthermore, a retardation film for widening the viewing angle can also be used. Examples of the spacer include columnar spacers made of glass particles, plastic particles, alumina particles, a photoresist material, and the like. Thereafter, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.

Specifically, the above-described components include a substrate having a common electrode made of a transparent conductive material, a pixel electrode made of a transparent conductive material, and a thin film transistor for controlling the pixel electrode provided in each pixel. By sandwiching the liquid crystal composition of the present invention between the substrates and setting the liquid crystal molecules in the liquid crystal composition to be substantially vertical when no voltage is applied, it is useful to achieve both high-speed response and suppression of display defects. A VA mode liquid crystal display element can be obtained. Here, “substantially vertical” includes a state having a desired pretilt angle from the vertical direction. The pretilt angle is preferably inclined by 1 ° from the vertical direction, and more preferably by 0.5 °.

In addition, the liquid crystal composition of the present invention is sandwiched between a common electrode made of a transparent conductive material and a pixel electrode for each pixel on one substrate, and the other substrate is a transparent insulating substrate, Useful IPS mode or FFS mode which has both high-speed response and suppression of display failure by setting the alignment film layer to induce homogeneous alignment on the substrate and setting the alignment direction of each alignment film to be parallel The liquid crystal display element can be obtained.

As a method for sandwiching the polymerizable compound-containing composition between the two substrates, a normal vacuum injection method or an ODF method can be used. However, in the present invention, it can be suitably used for a display element manufactured using the ODF method. In the ODF liquid crystal display device manufacturing process, a sealant such as epoxy photothermal combination curing is drawn on a backplane or frontplane substrate using a dispenser in a closed-loop bank shape, and then removed. A liquid crystal display element can be manufactured by bonding a front plane and a back plane after dropping a predetermined amount of the composition under air. The composition of the present invention can be suitably used because the composition can be stably dropped in the ODF process.

As a method for polymerizing a polymerizable compound, an appropriate polymerization rate is desirable in order to obtain good alignment performance of liquid crystals. Therefore, active energy rays such as ultraviolet rays or electron beams are irradiated singly or in combination or sequentially. The method of polymerizing by is preferred. When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used. Further, when the polymerization is carried out in a state where the polymerizable compound-containing composition is sandwiched between two substrates, at least the substrate on the irradiated surface side must be given adequate transparency to the active energy rays. Don't be. Moreover, after polymerizing only a specific part using a mask during light irradiation, the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the polymerizable compound-containing composition. The alternating electric field to be applied is preferably an alternating current having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on a desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In a horizontal electric field type MVA mode liquid crystal display element, the pretilt angle is preferably controlled from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.

The temperature at the time of irradiation is preferably within a temperature range in which the liquid crystal state of the composition of the present invention is maintained. Polymerization is preferably performed at a temperature close to room temperature, that is, typically at a temperature of 15 to 35 ° C. As a lamp for generating ultraviolet rays, a metal halide lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, or the like can be used. Moreover, as a wavelength of the ultraviolet-ray to irradiate, it is preferable to irradiate the ultraviolet-ray of the wavelength range which is not the absorption wavelength range of a composition, and it is preferable to cut and use an ultraviolet-ray as needed. The intensity of the irradiated ultraviolet light is preferably 0.1 mW / cm 2 to 100 W / cm 2, more preferably 2 mW / cm 2 to 50 W / cm 2. The amount of energy of ultraviolet rays to be irradiated can be adjusted as appropriate, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2. When irradiating with ultraviolet rays, the intensity may be changed. The time for irradiating with ultraviolet rays is appropriately selected depending on the intensity of the irradiated ultraviolet rays, but is preferably from 10 seconds to 3600 seconds, and more preferably from 10 seconds to 600 seconds.

The liquid crystal display device using the liquid crystal composition of the present invention is useful for achieving both high-speed response and suppression of display failure, and is particularly useful for a liquid crystal display device for active matrix driving, including VA mode, PSVA mode, It can be applied to PSA mode, IPS mode or ECB mode liquid crystal display elements.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.

In the examples, the measured characteristics are as follows.

T _NI : Nematic phase-isotropic liquid phase transition temperature (° C)
Δn: refractive index anisotropy at 25 ° C. Δε: dielectric anisotropy at 25 ° C. η: viscosity at 20 ° C. (mPa · s)
γ1: rotational viscosity at 25 ° C. (mPa · s)
VHR: Voltage holding ratio (%) at 60 ° C. under conditions of frequency 60 Hz and applied voltage 1 V
After 1000 hours VHR: Voltage holding ratio (%) at 60 ° C. under a condition of a frequency of 60 Hz and an applied voltage of 1 V after being left for 1000 hours at a high temperature of 90 °
Burn-in:
The burn-in evaluation of the liquid crystal display element is based on the following four-level evaluation of the afterimage level of the fixed pattern when the predetermined fixed pattern is displayed in the display area for 1000 hours and then the entire screen is uniformly displayed. went.

◎ No afterimage ○ Very little afterimage but acceptable level △ There is afterimage unacceptable level × Afterimage is quite bad Drop mark:
Evaluation of the drop marks of the liquid crystal display device was performed by the following four-stage evaluation of the drop marks that appeared white when the entire surface was displayed in black.

◎ No afterimage ○ Although there is a slight afterimage Acceptable level △ Without afterimage Unacceptable level × Afterimage fairly bad In addition, the following abbreviations are used for the description of compounds in the examples.
(Side chain)
-n -C _n H _{2n + 1} linear alkyl group with n carbon atoms n- C _n H _{2n + 1} -linear alkyl group with n carbon atoms -On -OC _n H _{2n + 1} carbon atoms n linear alkoxy group -V -CH = CH ₂
V- CH ₂ = CH-
-V1 -CH = CH-CH ₃
(Ring structure)

(Example 1, Example 2, Comparative Example 1 and Comparative Example 2)
A liquid crystal composition X shown below was prepared.

The physical properties of the liquid crystal composition X were as follows.

Next, a liquid crystal composition 1 was prepared in which all the compounds having an alkenyl side chain group in the liquid crystal composition X were replaced with compounds having an alkyl side chain group.

The physical properties of the liquid crystal composition 1 were as follows.

It is shown that the liquid crystal composition 1 containing a compound having an alkenyl side chain group has a rotational viscosity γ1 of about 15% lower than that of the liquid crystal composition X not containing it.

Next, Composition A and Composition B were prepared by adding 0.03% of the compound represented by Formula (I-1-1) or Formula (I-2-1) to 99.97% of Liquid Crystal Composition 1. did.
The physical property values thereof were almost the same as those of the liquid crystal composition 1.

Composition A (Example 1), Composition B (Example 2), Liquid crystal composition 1 containing no compound of general formula (I) (Comparative Example 1) and Liquid crystal composition containing no compound of general formula (I) The results of evaluation of VHR, afterimage and dropping marks of product X (Comparative Example 2) are shown in the following table.

A long-time high-temperature test of the liquid crystal composition 1 shown in Comparative Example 1 shows that the VHR has decreased from the initial stage, and the residual evaluation and drop mark evaluation are inferior, but the compound of the general formula (I) is added. In compositions A and B, the decrease in VHR was suppressed, and the residual evaluation and drop mark evaluation also showed good results. Even in the liquid crystal composition X not containing a compound having an alkenyl side chain group, a decrease in VHR was observed, and the residual evaluation and drop mark evaluation were inferior.
(Examples 3 to 6 and Comparative Examples 3 to 4)
Liquid crystal compositions 2 and 3 shown in the following table were prepared.

Next, a composition in which 0.03% of the compound represented by formula (I-1-1) or formula (I-2-1) is added to 99.97% of liquid crystal composition 2 and liquid crystal composition 3 C to Composition F were prepared.
The physical properties of the composition to which the compound represented by formula (I-1-1) or formula (I-2-1) was added were almost unchanged from the original liquid crystal composition.

Composition C (Example 3), Composition D (Example 4), Composition E (Example 5), Composition F (Example 6), Liquid crystal composition 2 containing no compound of general formula (I) The following table shows the results of evaluation of VHR, afterimages and dropping marks of the liquid crystal composition 3 (Comparative Example 4) not containing the compound of Comparative Example 3 and the general formula (I).

The composition containing the compound of the general formula (I) was able to suppress a decrease in VHR due to a long-time high-temperature test as compared with a composition other than that, and showed good results in residual evaluation and drop mark evaluation.
(Examples 7 to 10 and Comparative Examples 5 to 6)
Liquid crystal compositions 4 and 5 shown in the following table were prepared.

Next, a composition in which 0.03% of the compound represented by formula (I-1-1) or formula (I-2-1) is added to 99.97% of liquid crystal composition 4 and liquid crystal composition 5 G to Composition J were prepared.
The physical properties of the composition to which the compound represented by formula (I-1-1) or formula (I-2-1) was added were almost unchanged from the original liquid crystal composition.

Composition G (Example 7), Composition H (Example 8), Composition I (Example 9), Composition J (Example 10), Liquid crystal composition 4 containing no compound of general formula (I) The following table shows the results of evaluation of VHR, afterimages and dropping marks of the liquid crystal composition 5 (Comparative Example 6) not containing the compound of (Comparative Example 5) and the general formula (I).

The composition containing the compound of the general formula (I) was able to suppress a decrease in VHR due to a long-time high-temperature test as compared with a composition other than that, and showed good results in residual evaluation and drop mark evaluation.

Claims

Formula (I)

(Wherein R 1 represents a linear or branched alkyl group having 1 to 22 carbon atoms, and one or more CH 2 groups in the alkyl group are not directly adjacent to an oxygen atom. May be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF 2 O—, —OCF 2 —, and X 1 is — One or more compounds represented by CH 2 — or an oxygen atom)),
Formula (L-1) to Formula (L-6)

(Wherein R L11 to R L62 each independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one of which is an alkenyl group having 2 to 10 carbon atoms) X L61 and X L62 each independently represents a hydrogen atom or a fluorine atom, but at least one represents a hydrogen atom.) One or more compounds selected from the group consisting of compounds represented by A liquid crystal composition characterized by comprising:
Formula (N-1)

(Wherein, R N11 and R N12 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, and n N11 and n N12 are 0 or 1 And n N11 + n N12 represents 0 or 1.)
The nematic liquid crystal composition of Claim 1 which contains 1 type, or 2 or more types of compounds represented by these.
General formula (N-4)

(Wherein R 41 and R 42 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, X 41 is a single bond, —CH 2 CH 3. The liquid crystal composition according to claim 1, which contains one or more compounds represented by 2 — or —CH 2 O—, and n N41 represents 0 or 1. .
The content of the compound represented by the general formula (I) is 0.001% by mass to 1% by mass, and the content of the compound represented by the general formula (L-1) to the general formula (L-6) The liquid crystal composition according to claim 1, wherein the total is 5% by mass to 70% by mass.
Formula (XX)

(Wherein, X 201 and X 202 each independently represent a hydrogen atom or a methyl group,
Sp 201 and Sp 202 are each independently a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH 2 ) s —.
(Wherein s represents an integer of 2 to 7, and an oxygen atom is bonded to an aromatic ring),
Z 201 represents —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═ CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CY 1 ═CY 2 — (Wherein Y 1 and Y 2 each independently represents a fluorine atom or a hydrogen atom), —C≡C— or a single bond;
M 201 represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group or a single bond, and all 1,4-phenylene groups in the formula have an arbitrary hydrogen atom substituted with a fluorine atom. Also good. The liquid crystal composition according to claim 1, which contains a polymerizable compound represented by formula (1):
The liquid crystal display element using the liquid-crystal composition as described in any one of Claim 1 or 2.
A first substrate having a common electrode made of a transparent conductive material; a pixel electrode made of a transparent conductive material; a second substrate having a thin film transistor for controlling the pixel electrode provided in each pixel; A liquid crystal display element having a liquid crystal composition sandwiched between the substrate and the second substrate, wherein the alignment of liquid crystal molecules in the liquid crystal composition when no voltage is applied is substantially perpendicular to the substrate. A liquid crystal display device using the liquid crystal composition according to claim 1 as the liquid crystal composition.
A liquid crystal display device produced by using the nematic liquid crystal composition containing the polymerizable compound according to claim 5 and polymerizing the polymerizable compound contained in the liquid crystal composition with voltage applied or without voltage applied.
A first transparent insulating substrate, a second transparent insulating substrate, and a liquid crystal layer containing a liquid crystal composition sandwiched between the first substrate and the second substrate, In addition, a common electrode made of a transparent conductive material and a pixel electrode are provided for each pixel, and an alignment film layer for inducing homogeneous alignment is provided between the liquid crystal layer and the first substrate and the second substrate. A liquid crystal display element in which the alignment directions of the alignment films are parallel to each other, and the liquid crystal composition using the liquid crystal composition according to claim 1 as the liquid crystal composition.