CN112852444A - Liquid crystal composition and liquid crystal display element using same - Google Patents
Liquid crystal composition and liquid crystal display element using same Download PDFInfo
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Images
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a liquid crystal composition and a liquid crystal display element using the same. The present invention addresses the problem of providing a liquid crystal composition that is stable to heat and light and can maintain a high voltage holding ratio, and further providing a liquid crystal display element having excellent display quality by using the liquid crystal composition. The invention provides a liquid crystal composition containing 1 or more than 2 light stabilizers represented by a general formula (H) and a liquid crystal display element using the liquid crystal composition.
Description
Technical Field
The present invention relates to a liquid crystal composition useful as an electro-optical liquid crystal display material and a liquid crystal display element using the same.
Background
Liquid crystal display elements have been used in watches, electronic calculators, various measuring devices, panels for automobiles, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display panels, and the like. Typical examples of liquid crystal display systems include TN (twisted nematic) type, STN (super twisted nematic) type, VA (vertical alignment) type characterized by vertical alignment using a TFT (thin film transistor), IPS (in-plane switching) type/FFS (fringe field switching) type characterized by horizontal alignment, and the like.
Among these display systems, IPS type, ECB type (Electrically Controlled Birefringence), VA type, or csh (color super homeotropic) type have a characteristic of using a liquid crystal material exhibiting a negative dielectric anisotropy (Δ ∈). On the other hand, liquid crystal compositions having positive Δ ∈ are used for horizontal alignment displays such as TN type, STN type, and IPS type displays, and in recent years, driving methods have been reported in which a liquid crystal composition having positive Δ ∈ is vertically aligned when no voltage is applied, and display is performed by applying an IPS type/FFS type electric field. All of these driving methods require low-voltage driving, high-speed response, and a wide operating temperature range. That is, it is required to have a large absolute value of Δ ∈ and a small viscosity (. eta.), and a high nematic phase-isotropic liquid phase transition temperature (T)ni). In addition, it is necessary to adjust Δ n of the liquid crystal composition to an appropriate range in accordance with the setting of Δ n × d, which is the product of the refractive index anisotropy (Δ n) and the cell gap (d), in conjunction with the cell gap. In addition, in the case of applying a liquid crystal display element to a television or the like, high-speed response is important, and therefore rotational viscosity (γ) is required1) A small liquid crystal composition. In order to optimize Δ ∈, Δ n, and the like for each display element, the liquid crystal composition is generally composed of several to several tens of compounds.
In addition to the requirements for the physical properties of these liquid crystal compositions, the liquid crystal compositions used in liquid crystal display devices are also required to be stable against external stimuli such as moisture, air, heat, and light. If the stability against external stimuli is impaired, display defects such as burn-in and display unevenness occur in the liquid crystal display device, and it is generally considered that the Voltage Holding Ratio (VHR) must be high in order to suppress the display defects such as burn-in and display unevenness. For this reason, for example, it is known to use a liquid crystal composition in which an antioxidant, an ultraviolet absorber, or a light stabilizer is combined with a specific compound (patent documents 1 and 2).
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent application laid-open No. 2014-84460
[ patent document 2] Japanese patent application laid-open No. 2014-84462
Disclosure of Invention
Problems to be solved by the invention
In recent years, liquid crystal compositions are subjected to stronger light in the use environment and production process of liquid crystal display elements. Therefore, a liquid crystal composition having further high stability against external stimuli, particularly light, and a high VHR as compared with a liquid crystal composition to which known additives are added is required.
The present invention addresses the problem of providing a liquid crystal composition that is stable against external stimuli, particularly light, and that can maintain a high voltage holding ratio, and further providing a liquid crystal display element having excellent display quality by using the liquid crystal composition.
Means for solving the problems
The present inventors have conducted intensive studies and, as a result, have found that a liquid crystal composition containing a light stabilizer having a specific structure can solve the above problems, and have completed the present invention.
That is, the present invention provides a liquid crystal composition containing 1 or 2 or more light stabilizers represented by the general formula (H), and a liquid crystal display element using the liquid crystal composition.
[ solution 1]
(in the above general formula (H), Ra0Represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 3 to 12 carbon atoms,
Ra1、Ra2、Ra3and Ra4Each independently represents an alkyl group having 1 to 6 carbon atoms, or Ra1And Ra2And/or Ra3And Ra4May be formed together in a ring structure,
Ra5and Ra6Are respectively independentAnd (b) represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Ra0、Ra1、Ra2、Ra3、Ra4、Ra5and Ra6When a plurality of the compounds are present, they may be the same or different,
n represents a number of 0 or 1,
t represents a number of 1 to 4,
u represents a 2 x t-valent organic group forming a ring structure,
and the U has 1 or more polymerizable groups P in the groupH。)
ADVANTAGEOUS EFFECTS OF INVENTION
The liquid crystal composition of the present invention is stable to light and can maintain a high voltage holding ratio. Further, by using the liquid crystal composition of the present invention, a liquid crystal display element having excellent display quality in which display failure is not generated or suppressed can be provided.
Drawings
FIG. 1 is a schematic view showing an example of a liquid crystal display device of the present invention.
Description of the symbols
1: a liquid crystal display element; 2: a first substrate; 3: a second substrate; 4: a liquid crystal layer; 5: a pixel electrode layer; 6: a common electrode layer; 7. 8: a polarizing plate; 9: and a color filter.
Detailed Description
I. Liquid crystal composition
The liquid crystal composition of the present invention contains 1 or more light stabilizers represented by the general formula (H) and 1 or more liquid crystal compounds represented by the general formula (II).
The light stabilizer represented by the general formula (H) of the present invention is characterized by having a polymerizable group and a cyclic acetal skeleton. In the present specification, among the light stabilizers, a light stabilizer having a polymerizable group is referred to as a "polymerizable light stabilizer", and a light stabilizer having no polymerizable group is referred to as a "non-polymerizable light stabilizer" for the sake of distinction. Among the light stabilizers, those having an acetal skeleton in their molecular structure are referred to as "acetal-based light stabilizers", and those having no acetal skeleton are referred to as "non-acetal-based light stabilizers". That is, the light stabilizer represented by the general formula (H) of the present invention has both a polymerizable group and an acetal skeleton, and thus may be referred to as a "polymerizable acetal-based light stabilizer".
The polymerizable light stabilizer including the light stabilizer represented by the general formula (H) is not included in the polymerizable compound described later.
It is known that if a liquid crystal composition is subjected to an external stimulus such as light in a manufacturing process or a use environment of a liquid crystal display element, the liquid crystal composition is deteriorated to lower VHR. In particular, when a liquid crystal display element is manufactured by using a polymer stabilization technique typified by a PSA (polymer sustained alignment) technique, there are problems such as the following: the liquid crystal composition is easily deteriorated by being irradiated with ultraviolet rays having high intensity in the above-mentioned step, and as a result, VHR is easily decreased. Such a problem is a problem that may occur not only in a liquid crystal display element using the PSA technique.
Here, it is also considered to introduce a large amount of known additives in order to improve the effect of suppressing the photodegradation of the liquid crystal composition. However, if the additive is added in an excessive amount, there are problems as follows: the additive precipitates in the liquid crystal panel to degrade the display quality, or the additive itself causes the VHR to decrease.
In contrast, according to the liquid crystal composition of the present invention, even when the liquid crystal compound is decomposed by external stimulus such as ultraviolet rays or heat to generate a large amount of impurities, the light stabilizer represented by the general formula (H) traps the impurities, and thus the reduction of VHR due to the generation of the impurities can be suppressed. Here, the light stabilizer represented by the general formula (H) has a hindered amine structure, and therefore has a strong impurity trapping function, and also has an acetal skeleton, so that the light stabilizer has high solubility and excellent compatibility with a liquid crystal compound. Therefore, the light stabilizer represented by the general formula (H) can exhibit the same effect as a conventional non-acetal light stabilizer with a small content, and since it is not easily precipitated from the liquid crystal composition, a larger amount of the light stabilizer than a conventional light stabilizer can be added, and a larger amount of impurities can be captured to realize a high VHR.
In addition, according to the liquid crystal composition of the present invention, by containing the light stabilizer represented by the general formula (H), it is possible to suppress the reduction of VHR due to the presence of the light stabilizer. In detail, although a hindered amine-based light stabilizer conventionally used in a liquid crystal composition does not have a polymerization function (i.e., a polymerizable group), such a non-polymerizable light stabilizer has an effect of capturing impurities in a liquid crystal layer to improve reliability, and on the other hand, since the polarity is large, the compound itself becomes an ion conduction source to reduce VHR. On the other hand, since the light stabilizer represented by the general formula (H) has a polymerizable moiety (polymerizable group) and a polar moiety, the light stabilizer represented by the general formula (H) forms a polymer (polymer) by ultraviolet irradiation, and the main polymer can be fixed to the substrate interface after UV treatment. Thus, even when the panel is driven, impurities can be trapped by the polar portion on the polymer surface in a state where the polymer of the light stabilizer represented by the general formula (H) is fixed to the substrate. Thus, the light stabilizer represented by the general formula (H) does not itself serve as an ion conduction source, and VHR can be increased.
The above-described effect can be remarkably exhibited when the polymerizable compound is contained. When a liquid crystal display element is manufactured by using a polymer stabilization technique, a liquid crystal composition containing a polymerizable compound is irradiated with ultraviolet rays to polymerize the polymerizable compound. Includes a step of forming a polymer layer composed of a polymer of a polymerizable compound at a substrate interface of an element. When the liquid crystal composition of the present invention contains a polymerizable compound, the polymerizable group of the light stabilizer represented by the general formula (H) is reacted with a part of the polymerizable compound in the above step, and it is estimated that the light stabilizer represented by the general formula (H) is incorporated into the polymer layer formed by polymerization of the polymerizable compound. It is presumed that the light stabilizer represented by the general formula (H) introduced into the polymer layer as described above retains the function of trapping impurities and does not act as an ion conduction source by being immobilized on the polymer layer, and therefore, the reduction of VHR can be suppressed more effectively than the case of using a non-polymerizable light stabilizer.
In the present specification, the light stabilizer represented by the general formula (H) may be referred to as a compound represented by the general formula (H) or a compound (H). The liquid crystal compound represented by the general formula (II) may be referred to as only the compound represented by the general formula (II) or the compound (II).
Hereinafter, the compounds contained in the liquid crystal composition of the present invention will be described.
(1) A light stabilizer represented by the general formula (H)
The liquid crystal composition of the present invention contains 1 or more light stabilizers represented by the general formula (H).
[ solution 2]
(in the above general formula (H), Ra0Represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 3 to 12 carbon atoms,
Ra1、Ra2、Ra3and Ra4Each independently represents an alkyl group having 1 to 6 carbon atoms, or Ra1And Ra2And/or Ra3And Ra4May be formed together in a ring structure,
Ra5and Ra6Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Ra0、Ra1、Ra2、Ra3、Ra4、Ra5and Ra6When a plurality of the compounds are present, they may be the same or different,
n represents a number of 0 or 1,
t represents a number of 1 to 4,
u represents a 2 x t-valent organic group forming a ring structure,
and the U has 1 or more polymerizable groups P in the groupH。)
In the general formula (H), R is for improving the deterioration resistance against external stimulia0Hydrogen atom or hydroxyl group is preferable, and hydrogen atom is particularly preferable. In addition, R is for improving the compatibility with the liquid crystal compounda0Preferably an alkyl group having 1 to 12 carbon atoms or a carbon atomA number of 3 to 12 alkenyl groups.
In the general formula (H), Ra1、Ra2、Ra3And Ra4Each independently preferably represents an alkyl group having 1 to 4 carbon atoms, and particularly preferably represents a methyl group. In addition, R is preferable for easy removal of polar impurities mixed during productiona1And Ra2And/or Ra3And Ra4Together forming a ring structure.
In the general formula (H), Ra5And Ra6Each independently preferably represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and particularly preferably represents a hydrogen atom from the viewpoint of ease of production.
In the general formula (H), n is preferably 1.
In the general formula (H), t preferably represents 1 or 2, and particularly preferably 1, in order to improve the storage stability of the liquid crystal composition. In addition, t preferably represents 3 or 4 in order to improve the deterioration resistance against external stimuli. This is because the number of hindered amine structures per unit weight is increased, and the deterioration resistance against external stimuli can be improved.
In the general formula (H), U represents a 2 Xt-valent organic group which is connected with 2 oxygen atoms to form a ring structure, and more than 1 polymerizable group P is contained in the groupH. When the number of the polymerizable groups is large, high reactivity and high VHR can be achieved, and therefore, it is preferable, but if it is too large, solubility is lowered and precipitation becomes easy. On the other hand, if the number of polymerizable groups is small, the reactivity is poor, and it is difficult to obtain the effect of improving VHR. Thus, to achieve a compromise between reactivity, VHR and solubility, P in formula (H)HThe number of (a) is preferably 1,2,3 or 4, preferably 1,2 or 3, preferably 1 or 2.
Polymerizable group PHPreferably, a spacer (hereinafter, sometimes referred to as Sp)H. ) And are connected. That is, in the general formula (H), the U preferably has 1 or more-Sp in the groupH-PH。
In the general formula (H), PHPreferably a group selected from the group represented by the formulae (P-1) to (P-17). In the general formula (H), a plurality of P are presentHWhen there are more than 1PHAre respectively independently superiorSelected from the group represented by the formulae (P-1) to (P-17).
[ solution 3]
(wherein the black dots represent the connecting keys.)
Among these, PHPreferably a group selected from the group represented by the formula (P-1), the formula (P-2), the formula (P-5), the formula (P-6), the formula (P-8), the formula (P-12), the formula (P-14) and the formula (P-17), more preferably a group selected from the group represented by the formula (P-1), the formula (P-2), the formula (P-8), the formula (P-12) and the formula (P-14), and still more preferably a group represented by the formula (P-1) or the formula (P-2).
In the general formula (H), Sp represents a spacerHRepresents a single bond, or a linear or branched alkylene group having 1 to 12 carbon atoms, 1-CH in the alkylene group2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. Among them SpHPreferably represents a single bond or a linear alkylene group having 1 to 12 carbon atoms (1 or not adjacent 2 or more-CH groups in the group)2-may be substituted by-O-, -COO-or-OCO-. ) Preferably represents a single bond or a linear alkylene group having 1 to 6 carbon atoms (1 or 2 or more-CH groups not adjacent to each other in the group)2-may be substituted by-O-, -COO-or-OCO-. ) Preferably represents a single bond or a linear alkylene group having 1 to 4 carbon atoms (1 or not adjacent 2 or more-CH groups in the group)2-may be substituted by-O-, -COO-or-OCO-. ) Particularly preferred is a single bond.
In the general formula (H), U is not particularly limited as long as it is an organic group having a valence of 2 × t, and when t in the general formula (H) represents 1, U is preferably a structure represented by the general formula (U-1).
[ solution 4]
(in the general formula (U-1), the dotted lines each represent a bond to an oxygen atom in the general formula (H),
Ra7and Ra8Each independently represents a hydrogen atom or a 1-valent organic group, or Ra7And Ra8May be formed together in a ring structure,
m represents a number of 0 or 1,
at least Ra8Having more than 1-SpH-PH。)
U in the general formula (H) has a structure represented by the general formula (U-1), and thus the storage stability of the liquid crystal composition can be improved.
Ra7Preferably represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or-SpH-PH. Alkyl or Sp H1 of-CH present in2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. Among them, Ra7Preferably represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms (1-CH present in the alkyl group)2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. ) or-SpH-PHPreferably, it represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
m particularly preferably represents 1. This is because the light stabilizer represented by the general formula (H) easily takes a linear structure similar to that of a general liquid crystal compound, and as a result, the compatibility with the liquid crystal compound can be improved.
Ra8Provided that it is an amino acid having 1 or more-SpH-PHThe structure (d) is not particularly limited, and is preferably a structure represented by the general formula (r) from the viewpoint of improving compatibility with the liquid crystal composition.
[ solution 5]
(in the general formula (r), Spa1Represents a single bond, -O-, -CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH＝CH-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-OOCO-、-OCH2CH2O-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-CH＝C(CH3)COO-、-OCOC(CH3)＝CH-、-CH2-CH(CH3)COO-、-OCOCH(CH3)-CH2Or a linear or branched alkylene group having 1 to 10 carbon atoms, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2May be substituted by-O-, -COO-or-OCO-,
Spa2represents a single bond, -O-, -CO-, -CH-, -CF-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF2O-、-OCF2-、-CH＝CHCOO-、-OCOCH＝CH-、-CH＝C(CH3)COO-、-OCOC(CH3)＝CH-、-CH2-CH(CH3)COO-、-OCOCH(CH3)-CH2-、-OCH2CH2O-, or a C1-10 linear or branched alkylene group, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2May be substituted by-O-, -COO-or-OCO-,
Aa1and Aa2Each independently represents a group selected from the group consisting of a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring and a 2-valent condensed polycyclic ring, and 1 or more hydrogen atoms in the ring structure of these groups may be replaced by Li1The substitution is carried out by the following steps,
Li1represents a halogen atom, a cyano group, a nitro group or-SpH-PH1-valent organic radical Ki1A C1-30 linear or branched alkyl group or a C1-30 linear or branched haloalkyl group, or-CH in the alkyl group or haloalkyl group2-may be substituted with-CH ═ CH-, -C.ident.C-, -O-, -NH-, -COO-, -OCO-or-OCOO-but-O-is not continuous,
the aforementioned 1-valent organic group Ki1Represents a group represented by the following general formula (K1),
[ solution 6]
(in the formula, Rk0To Rk6And nkAre respectively R in the general formula (H)a0To Ra6And n is as defined for Rk7And mkAre respectively R in the general formula (U-1)a7And m is as defined. Denotes a bond. )
Ra9Represents a hydrogen atom, -SpH-PHA C1-30 linear or branched alkyl group or a C1-30 linear or branched haloalkyl group, 1-CH in the alkyl group or haloalkyl group2-or 2 or more-CH not adjacent2-may be substituted but-oxo-discontinuous by-CH ═ CH-, -C.ident.C-, -O-, -S-, -NH-, -CO-, -COO-, -OCO-or-OCOO-,
p and q each represents an integer of 0, 1,2 or 3,
when p represents 2 or 3, a plurality of Spa1May be the same or different, and a plurality of the above-mentioned A's may be presenta1Which may be the same or different from each other,
when q represents 2 or 3, a plurality of Spa2May be the same or different, and a plurality of the above-mentioned A's may be presenta2May be the same or different
PHRepresents a polymerizable group, SpHRepresents a spacer group.
Wherein the general formula (r) has more than 1-SpH-PH. Wherein denotes a bond. )
Spa1Preferably represents a single bond, -CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH＝CH-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-OOCO-、-OCH2CH2O-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-CH＝C(CH3)COO-、-OCOC(CH3)＝CH-、-CH2-CH(CH3) COO-, or-OCOCH (CH)3)-CH2-. More preferably, Spa1Is a single bond, -OCH2-、-CH2O-、-COO-、-C2H4-、-CF2O-or-OCF2-。Spa1Is a single bond, -OCH2-、-CH2O-、-COO-、-C2H4-、-CF2O-or-OCF2In the case of (ii), the light stabilizer represented by the general formula (H) further improves the compatibility with the liquid crystal compound and is less likely to precipitate even when stored at low temperatures.
Spa2Preferably represents a single bond or a linear alkylene group having 1 to 10 carbon atoms, more preferably a single bond or a linear alkylene group having 1 to 8 carbon atoms, still more preferably a single bond or a linear alkylene group having 1 to 6 carbon atoms, and particularly preferably a single bond. In the linear alkylene radical, 1-CH present in the radical2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-.
Aa1And Aa2Each independently represents a group selected from the group consisting of a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring, and a 2-valent condensed polycyclic group. Among these, A is a compound capable of improving the storage stability of the liquid crystal compositiona1And Aa2Each independently is preferably a group selected from the group consisting of the following.
(a)1, 4-cyclohexylene (1-CH present in the radical)2-or 2 or more-CH not adjacent2-may be substituted by-O-. )
(b)1, 4-phenylene (1-CH-present in the radical or more than 2 non-adjacent-CH-may be substituted by-N) and
(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)
Aa1And Aa2In the group represented, 1 or more hydrogen atoms in the ring structure may be replaced by Li1And (4) substitution. That is, the above-mentioned group (a), group (b) and group (c) may be represented by Li1And (4) substitution. Among these, L is a group capable of improving the solubility in the liquid crystal compositioni1Preferably a C1-6 linear or branched alkyl group,A C1-6 linear or branched haloalkyl group, a C1-6 linear or branched alkoxy group, a C1-6 linear or branched haloalkoxy group, a fluorine atom, a cyano group or-SpH-PHMore preferably represents a fluorine atom, -SpH-PHAnd a C1-4 linear alkyl group.
Aa1And Aa2When plural, plural A are preferablea1And Aa2All are groups having an aromatic ring. This is because of the effect of excellent reactivity to ultraviolet rays.
Ra9Preferably represents a hydrogen atom, a linear alkyl group having 1 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms or-SpH-PH(the Sp H1 of the radical-CH2-or 2 or more-CH not adjacent2-may be substituted by-O-or-CH ═ CH) -), more preferably represents-SpH-PH(Sp H1 of the radical-CH2-or 2 or more-CH not adjacent2-may be substituted by-O-or-CH ═ CH-. ).
In the general formula (R), when p and q represent 0, Ra9represents-SpH-PH. At this time SpHPreferably represents a linear or branched alkylene group having 1 to 12 carbon atoms, 1-CH in the alkylene group2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. Among these, in the above case, Ra9Sp in (1)HIt is preferably a linear alkylene group having 1 to 6 carbon atoms or a linear oxyalkylene group having 1 to 6 carbon atoms.
In the general formula (r), at least one of p and q represents an integer of 1,2 or 3, and 1 or more Aa1And Aa2At least 1 of the ring structures having more than 1 hydrogen atom-SpH-PHWhen substituted, Ra9Can represent-SpH-PHIt may also represent a hydrogen atom, a linear alkyl group having 1 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms.
Of the structures represented by the general formula (r), those represented by the following general formula (r-1) or (r-2) are preferable.
[ solution 7]
*-SpH-PH (r-1)
(wherein SpHAnd PHRespectively, as defined above. Wherein denotes a bond. )
[ solution 8]
(wherein Spa1、Spa2、Aa1、Aa2、Ra9And q represents Sp in the general formula (r)a1、Spa2、Aa1、Aa2、Ra9And q is as defined.
L1And L2Each independently represents the same definition as L in the general formula (r). Ring Aa1And ring Aa2L in (1)1And L2The positions of (a) and (b) are respectively arbitrary positions.
nr1 and nr2 each independently represent 0, 1,2 or 3.
q represents 2 or 3, Spa2And Aa2When there are multiple, multiple Spa2And a plurality of Aa2Each may be the same or different.
L1And L2When there are multiple, multiple L1And a plurality of L2Each may be the same or different.
Wherein the general formula (r-2) has more than 1-SpH-PH. Wherein denotes a bond. )
In the general formula (R-2), R is preferreda9And Aa1Having 1 substituent L1At least one of them represents-SpH-PH. When q represents 1,2 or 3, R is preferablya9、Aa1Having 1 substituent L1And Aa2Having 1 substituent L2At least any one of (a) and (b) represents SpH-PH。
When t in the general formula (H) represents 2, U is preferably a structure represented by the general formula (U-2). The light stabilizer represented by the general formula (H) can improve the deterioration resistance against external stimuli.
[ solution 9]
(wherein each of the dotted lines represents a bond to an oxygen atom, each of lc and oc independently represents the same definition as m in the formula (U-1),
Rc1and Rc2Each independently represents R in the general formula (U-1)a7The same definition is given to the same,
v represents an organic group having a valence of 2.
Wherein the general formula (U-2) has more than 1-SpH-PH。)
Rc1And Rc2Preferably represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or-SpH-PH. The alkyl group or Sp H1 of-CH present in2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-.
Wherein R isc1And Rc2Each independently preferably represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or-SpH-PHPreferably represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or-SpH-PHPreferably represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or-SpH-PHPreferably represents a hydrogen atom, a methyl group, an ethyl group or an-Sp groupH-PH。
The general formula (U-2) is preferably a structure represented by the general formula (U-2-i).
[ solution 10]
(wherein the dotted lines each represent a bond to an oxygen atom, Rc1、Rc2Lc and oc represent R in the general formula (U-2)c1、Rc2Lc, lc and oc are the same as defined,
Spacrepresents a single bond or an alkylene group having 1 to 12 carbon atoms, 1-CH present in the alkylene group2-or 2 or more-CH not adjacent2May be substituted by-O-, -COO-, -OCO-, -CH-or-C.ident.C-, and more than 1 hydrogen atom in the alkylene group may be substituted by-SpH-PHAnd (4) substitution.
Wherein the general formula (U-2-i) has more than 1-SpH-PH。)
Further, the general formula (U-2) is preferably a structure represented by the general formula (U-2-ii).
[ solution 11]
(wherein the dotted lines each represent a bond to an oxygen atom, and Rc1、Rc2Lc and oc represent R in the general formula (U-2)c1、Rc2Lc, lc and oc are the same as defined,
Spac1and Spac3Respectively represents Sp in the general formula (r)a1The same definition is given to the same,
Spac2、Aac1and Aac2Respectively represents Sp in the general formula (r)a2、Aa1And Aac1Same definition, a plurality of Spac2And a plurality of Aac2Each of which may be the same or different,
pe represents 1 or 2.
Wherein the general formula (U-2-ii) has more than 1-SpH-PH。)
When t in the general formula (H) represents 3 or 4, U is preferably a structure represented by the general formula (U-3). This is because the ability of the light stabilizer represented by the general formula (H) to resist light deterioration can be improved.
[ solution 12]
(wherein the dotted line represents a bond to an oxygen atom,
lf represents the same definition as m in the general formula (U-1),
Rf7r in the general formula (U-1)a7The same definition is given to the same,
Spaf1and Spaf2Respectively represents Sp in the general formula (r)a2The same definition is given to the same,
Aaf1represents a in the general formula (r)a1The same definition is given to the same,
pf represents 0, 1 or 2,
tf represents a number of 3 or 4,
Vfdenotes a group having a valence of 3 or 4, VfThe valence of (a) is the same number as the number represented by tf,
Spaf1、Spaf2and Aaf1When there are more than one, more than one Spaf1A plurality of Spaf2And a plurality of Aaf1Each may be the same or different.
Wherein the general formula (U-3) has more than 1-SpH-PH，PHRepresents a polymerizable group. )
lf particularly preferably represents 1.
Rf7Preferably represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or-SpH-PH. The alkyl group or Sp H1 of-CH present in2-or 2 or more-CH not adjacent2-may be substituted by-O-, -COO-, -OCO-, -CH ═ CH-, or-C ≡ C-. Wherein R isf7Preferably represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or-SpH-PHPreferably represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or-SpH-PHPreferably represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or-SpH-PHMore preferably represents a hydrogen atom, a methyl group, an ethyl group or-SpH-PH。
When tf in the general formula (U-3) represents 3, i.e., VfWhen the valence of (3) is VfPreferably represents a hydrocarbon group having 1 to 15 carbon atoms, the carbon atoms in the hydrocarbon group being present1 or 2 or more-CH not adjacent to2-may be independently-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH-COO-, -CH-OCO-, -COO-CH-, -OCO-CH-, -CH-, -CF-, -OCF ═ CH-, -OCF ═ CH-, -OCO-CO-O-CO-, -CH-COO-, -OCO-CH-CF-and-OCF-O-CO2-、-CF2O-or-C ≡ C-substitution. In addition, more than 1 hydrogen atom present in the hydrocarbon group may be replaced by-SpH-PHAnd (4) substitution.
VfMore preferably a group selected from the group represented by the formulae (V3-1) to (V3-12).
[ solution 13]
(R in the formulav31And Rv32Represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms or-SpH-PHThe alkyl group or Sp H1 or 2 or more-CH present in2-each independently may be substituted by-O-, -S-, -CH ═ CH-, -C ≡ C-, -CO-O-, -O-CO-. Further, the hydrogen atom in the cyclic structure may be substituted by a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a triethylsilyl group, a dimethylsilyl group, a thioisocyano group, an alkyl group having 1 to 12 carbon atoms, or-SpH-PHSubstituted, 1 or not adjacent 2 or more-CH present in the alkyl group2-may be independently-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH-COO-, -CH-OCO-, -COO-CH-, -OCO-CH-, -CH-, -CF-, -OCF ═ CH-, -OCF ═ CH-, -OCO-CO-O-CO-, -CH-COO-, -OCO-CH-CF-and-OCF-O-CO2-、-CF2O-or-C ≡ C-substitution. The black dots in the formula represent the connecting bonds. )
In the formulae (V3-1) and (V3-2), RV31And RV32Each independently preferably represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms or-SpH-PHIn addition, a linear chain is preferable.
The groups represented by the formulae (V3-4) to (V3-12) are each independently preferably unsubstituted or each hydrogen atom in the group is substituted by a cyano group, a fluorine atom, a chlorine atom, a methyl group, a methoxy group or an-SpH-PHAnd (4) substitution.
V is easy to obtain raw materials and easy to producefParticularly preferably represents a group selected from the group consisting of groups represented by the formulae (V3-1), the formulae (V3-2) and unsubstituted formulae (V3-3) to (V3-12).
When tf in the general formula (U-3) represents 4, i.e., VfWhen the valence of (3) is 4, VfPreferably represents a hydrocarbon group having 1 to 15 carbon atoms, 1 or 2 or more-CH groups not adjacent to each other being present in the carbon atoms in the hydrocarbon group2-may be independently-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH-COO-, -CH-OCO-, -COO-CH-, -OCO-CH-, -CH-, -CF-, -OCF ═ CH-, -OCF ═ CH-, -OCO-CO-O-CO-, -CH-COO-, -OCO-CH-CF-and-OCF-O-CO2-、-CF2O-or-C ≡ C-substitution. In addition, more than 1 hydrogen atom present in the hydrocarbon group may be replaced by-SpH-PHAnd (4) substitution.
VfMore preferably a group selected from the group represented by the formulae (V4-1) to (V4-21).
[ solution 14]
(in the formulae (V4-1) to (V4-21), the hydrogen atom in the cyclic structure may be replaced by a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a triethylsilyl group, a dimethylsilyl group, a thioisocyano group, an alkyl group having 1 to 12 carbon atoms, or-SpH-PHSubstituted, the alkyl or Sp H1 or 2 or more-CH not adjacent to each other present in2-may be independently substituted by-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH-COO-, -CH-OCO-,-COO-CH＝CH-、-OCO-CH＝CH-、-CH＝CH-、-CF＝CF-、-OCF2-、-CF2O-or-C ≡ C-substitution. The black dots in the formula represent the connecting bonds. )
The groups represented by the formulae (V4-3) to (V4-21) are each independently preferably unsubstituted or a hydrogen atom in the formulae is substituted by a cyano group, a fluorine atom, a chlorine atom, a methyl group, a methoxy group or an-SpH-PHAnd (4) substitution.
V is easy to obtain raw materials and easy to producefParticularly preferably represents a group selected from the group consisting of formula (V4-1), formula (V4-2) and unsubstituted formula (V4-3) to formula (V4-21).
Preferred examples of the light stabilizer represented by the general formula (H) include compounds represented by the general formula (H-I).
[ solution 15]
(in the general formula (H-I), Ra0R in the general formula (H)a0The same definition is given to the same,
Ra7、Ra9and m represents R in the general formula (U-1)a7、Ra9The same definition as that of m is applied,
Aa1、Aa2、Spa1、Spa2p and q each represents a group represented by the formula (r)a1、Aa2、Spa1、Spa2P and q are as defined.
Wherein the general formula (H-I) has more than 1-SpH-PH。)
Other preferable examples of the light stabilizer represented by the general formula (H) include compounds represented by the general formula (H-II).
[ solution 16]
(in the general formula (H-II), Ra01And Ra02Respectively represent R in the general formula (H)a0The same definition is given to the same,
Rc1、Rc2lc, and oc represent the same as R in the general formula (U-2)c1、Rc2Lc, and oc are the same as defined,
Spac1and Spac3Respectively represents Sp in the general formula (r)a1The same definition is given to the same,
Spac2、Aac1and Aac2Respectively represents Sp in the general formula (r)a2、Aa1And Aac1Same definition, a plurality of Spac2And a plurality of Aac2Each of which may be the same or different,
pe represents 1 or 2.
Wherein the general formula (H-II) has more than 1-SpH-PH。)
Specific examples of the light stabilizer represented by the general formula (H) include compounds represented by the following general formulae (H-1) to (H-27), but the light stabilizer is not limited thereto.
[ solution 17]
[ solution 18]
[ solution 19]
[ solution 20]
(in the above general formulae (H-1) to (H-27), Ra0R in the general formula (H)a0The same definition is given to the same,
Ra7、Ra9and m represents R in the general formula (U-1)a7、Ra9The same definition as that of m is applied,
Aa1represents a in the general formula (r)a1The same definition is given to the same,
Aa21and Aa22Each independently represents a in the general formula (r)a2The same definition is given to the same,
l1 and L2 each represent the same definition as L1 and L2 in the general formula (r), and Aa1L in (1)1Position of (A) anda21and Aa22L in (1)2The positions of (a) and (b) are respectively any positions,
nr11 represents the same definition as nr1 in the general formula (r-2),
nr21 and nr22 each represent the same definition as nr2 in the general formula (r-2). Wherein the formula has more than 1-SpH-PH，SpHAnd PHRespectively represents Sp in the general formula (H)HAnd PHThe same definition. )
As a more specific embodiment of the light stabilizer represented by the general formula (H), compounds represented by the following formulae (H-I-1) to (H-I-38) and formulae (H-II-1) to (H-II-2) can be exemplified, but the compounds are not limited thereto.
[ solution 21]
[ solution 22]
[ solution 23]
[ solution 24]
[ solution 25]
[ solution 26]
[ solution 27]
From the viewpoint of VHR improvement, the total amount of the light stabilizer represented by the general formula (H) is preferably in the range of 0.01 to 5% by mass, preferably in the range of 0.01 to 0.5% by mass, preferably in the range of 0.01 to 0.3% by mass, further preferably in the range of 0.02 to 0.3% by mass, and particularly preferably in the range of 0.05 to 0.25% by mass, relative to the total amount of the liquid crystal composition of the present invention.
From the viewpoint of sufficiently suppressing deposition from the liquid crystal composition, the total amount of the light stabilizer represented by the general formula (H) is preferably in the range of 0.005 to 1% by mass, more preferably in the range of 0.005 to 0.5% by mass, and further preferably in the range of 0.005 to 0.1% by mass, relative to the total amount of the liquid crystal composition of the present invention.
In order to achieve both VHR and solubility, the total amount of the light stabilizer represented by the general formula (H) is preferably in the range of 0.01 to 1% by mass, preferably in the range of 0.025 to 0.5% by mass, more preferably in the range of 0.03 to 0.3% by mass, and particularly preferably in the range of 0.05 to 0.1% by mass, relative to the total amount of the liquid crystal composition of the present invention.
(2) A compound represented by the general formula (II)
The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (II).
[ solution 28]
(in the general formula (II), RII1Represents an alkyl group having 1 to 10 carbon atoms, 1 or non-adjacent 2 or more-CH groups in the alkyl group2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
AII1and AII2Each independently represents a group selected from the group consisting of,
(a)1, 4-cyclohexylene (1-CH present in the radical)2-or 2 or more-CH not adjacent2-may be substituted by-O-. ) A
(b)1, 4-phenylene (1-CH-present in the radical or more than 2 non-adjacent-CH-may be substituted by-N) and
(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)
The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
ZII1represents a single bond, -CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
YII1represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, 1 or non-adjacent 2 or more-CH groups in the alkyl group2-each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, and 1 or 2 or more hydrogen atoms in the alkyl group may be substituted by fluorine atoms,
mII1represents 1,2,3 or 4, mII1When 2,3 or 4 is represented, a plurality of AII1And a plurality of ZII1Each may be the same or different. )
The liquid crystal composition of the present invention can adjust the magnitude of dielectric anisotropy by combining 1 or 2 or more compounds represented by the above general formula (II). The liquid crystal composition of the present invention may be a negative liquid crystal composition having a negative dielectric anisotropy (Δ ∈) and an absolute value (| Δ ∈ |) of 2 or more, or a positive liquid crystal composition having a positive dielectric anisotropy (Δ ∈) and an absolute value (| Δ |) of 1.5 or more. The values of the specific dielectric anisotropy are described later.
Here, the liquid crystal composition of the present invention preferably contains 1 or 2 or more species of at least 1Z of the above general formula (II)II1represents-CH2A compound of O-. That is, the liquid crystal composition of the present invention preferably contains m in the general formula (II)II1Is 1 or ZII1represents-CH2O-、mII1A number of Z in the case of 2,3 or 4II1At least 1 of them represents-CH2A compound of O-. Among these ZII1represents-CH2O-is preferably substituted with-CH2O-oxygen atom-linked Ring (A)II1Or AII2) Having 1 or 2 or more hydrogen atoms substituted by fluorine atoms, particularly preferably with-CH 21 or 2 or more hydrogen atoms of the ring to which the oxygen atom of O-is bonded are substituted with fluorine atoms, and at least 1 hydrogen atom of the same ring is substituted with an alkoxy group. Even if the structure includes 2 ring structures adjacent to each other with-CH interposed therebetween2In the case of a liquid crystal compound having a structure in which linking groups represented by O-are linked, the combination of the light stabilizer represented by the general formula (H) can suppress deterioration of the liquid crystal compound, and the physical properties of the liquid crystal composition can be improved by the combination of the liquid crystal compounds.
In the general formula (II), at least 1ZII1represents-CH2The total content of the O-compound is preferably 10 mass% or more, 20 mass% or more, and 30 mass% or more, and is preferably 70 mass% or less and 50 mass% or less, based on the total amount of the liquid crystal composition of the present invention% or less, 40 mass% or less. At least 1Z in the general formula (II)II1represents-CH2Specifically, the total content of the O-compounds is in the range of 10 to 70 mass%, in the range of 20 to 50 mass%, and in the range of 30 to 40 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (II) may be a liquid crystal compound having negative dielectric anisotropy (Δ ∈) (first embodiment), a liquid crystal compound having positive dielectric anisotropy (Δ ∈) (first embodiment), or a nonpolar liquid crystal compound having a dielectric anisotropy (Δ ∈) in the vicinity of 0 (third embodiment), depending on the dielectric anisotropy. The dielectric anisotropy of the compound represented by the general formula (II) was set to a value at 25 ℃. Hereinafter, each embodiment will be described with respect to the compound represented by the general formula (II).
[1] A first formula of the compound represented by the general formula (II)
A first embodiment (hereinafter, sometimes referred to as a first embodiment compound) of the compound represented by the general formula (II) is a liquid crystal compound having a negative dielectric anisotropy (Δ ∈). In the compound of the first embodiment, Δ ∈ is preferably negative in sign and greater in absolute value than 2, and more preferably greater in absolute value than 3.
Examples of the compound of the first embodiment include compounds selected from the group of compounds represented by the following general formulae (N-1) to (N-3).
[ solution 29]
(in the formula, RN11、RN12、RN21、RN22、RN31And RN32Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
AN11、AN12、AN21、AN22、AN31and AN32Each independently represents a group selected from the group consisting of,
(a)1, 4-cyclohexylene (1-CH present in the radical)2-or 2 or more-CH not adjacent2-may be substituted by-O-. )
(b)1, 4-phenylene (1-CH-present in the radical or more than 2 non-adjacent-CH-may be substituted by-N) and
(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)
The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
ZN11、ZN12、ZN21、ZN22、ZN31and ZN32Each independently represents a single bond, -CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
XN21represents a hydrogen atom or a fluorine atom,
TN31represents-CH2-or an oxygen atom,
nN11、nN12、nN21、nN22、nN31and nN32Each independently represents an integer of 0 to 3, nN11+nN12、nN21+nN22And nN31+nN32Independently of one another is 1,2 or 3,
AN11to AN32、ZN11To ZN32When a plurality of them exist, they may be the same or different. Wherein the compound represented by the general formula (N-1) is excluded from the general formula (N-2) and the general formula (N-3), and the compound represented by the general formula (N-2) is excluded from the general formula (N-3). )
When the liquid crystal composition of the present invention has a negative dielectric anisotropy (. DELTA.. di-elect cons.) at 25 ℃, the liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-1), (N-2) and (N-3).
In the general formulae (N-1), (N-2) and (N-3), RN11、RN12、RN21、RN22、RN31And RN32Independently, the alkyl group has 1 to 8 carbon atoms, the alkoxy group has 1 to 8 carbon atoms, the alkenyl group has 2 to 8 carbon atoms or the alkenyloxy group has 2 to 8 carbon atoms, the alkyl group has 1 to 5 carbon atoms, the alkoxy group has 1 to 5 carbon atoms, the alkenyl group has 2 to 5 carbon atoms or the alkenyloxy group has 2 to 5 carbon atoms is preferable, the alkyl group has 1 to 5 carbon atoms or the alkenyl group has 2 to 5 carbon atoms is more preferable, the alkyl group has 2 to 5 carbon atoms or the alkenyl group has 2 to 3 carbon atoms is more preferable, and the alkenyl group (propenyl group) has 3 carbon atoms is particularly preferable.
In addition, RN11、RN12、RN21、RN22、RN31And RN32When the ring structures to which they are respectively bonded are phenyl (aromatic), RN11、RN12、RN21、RN22、RN31And RN32Independently, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferable. In another aspect, RN11、RN12、RN21、RN22、RN31And RN32When the ring structures to which the compounds are bonded are saturated ring structures such as cyclohexane, pyran and dioxane, R isN11、RN12、RN21、RN22、RN31And RN32Independently, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable.
For stabilizing the nematic phase, RN11、RN12、RN21、RN22、RN31And RN32In (b), the total of carbon atoms and oxygen atoms is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5). Black dots in the formulae (R1) to (R5) represent carbon atoms in the ring structure to which the alkenyl group is attached.
[ solution 30]
When an increase of Δ n is required, AN11、AN12、AN21、AN22、AN31And AN32Each independently preferably aromatic. On the other hand, to improve response speed, AN11、AN12、AN21、AN22、AN31And AN32Each independently preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Among them AN11、AN12、AN21、AN22、AN31And AN32Each independently preferably represents any one of the following structures.
[ solution 31]
Further, AN11、AN12、AN21、AN22、AN31And AN32Each independently preferably represents trans-1, 4-cyclohexylene or 1, 4-phenylene.
ZN11、ZN12、ZN21、ZN22、ZN31And ZN32Each independently preferably represents-CH2O-、-CF2O-、-CH2CH2-、-CF2CF2-or a single bond, further preferably-CH2O-、-CH2CH2-or single bondParticularly preferred is-CH2O-or a single bond.
XN21Fluorine atoms are preferred.
TN31Oxygen atoms are preferred.
nN11+nN12、nN21+nN22And nN31+nN32Preferably 1 or 2, preferably nN11Is 1 and nN12A combination of 0, nN11Is 2 and nN12A combination of 0, nN11Is 1 and nN12Is a combination of 1, nN11Is 2 and nN12Is a combination of 1, nN21Is 1 and nN22A combination of 0, nN21Is 2 and nN22A combination of 0, nN31Is 1 and nN32A combination of 0, nN31Is 2 and nN32Is a combination of 0.
The liquid crystal composition of the present invention preferably contains 1 or 2 or more kinds of Z selected from the group consisting of Z in the general formula (N-1)N11And ZN12At least 1 of (a) represents-CH2O-compound, Z in the general formula (N-2)N21And ZN22At least 1 of (a) represents-CH2O-compound, and Z in the general formula (N-3)N31And ZN32At least 1 of (a) represents-CH2A compound of the group consisting of compounds of O-. This is because these compounds have-CH in their molecular structure2A linking group represented by O-can realize the above-mentioned structure having a-CH group2The effect of using a compound having a linking group represented by O-in combination with a light stabilizer represented by the general formula (H).
The lower limit of the content of the compound represented by the formula (N-1) is preferably 0 mass%, 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the formula (N-1) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The upper limit and the lower limit of the content of the compound represented by the formula (N-2), and the upper limit and the lower limit of the content of the compound represented by the formula (N-3) are preferably the same as the upper limit and the lower limit of the content of the compound represented by the formula (N-1), respectively.
When a composition having a low viscosity and a high response speed is required for the liquid crystal composition of the present invention, the lower limit value and the upper limit value are preferably low. Further, when the Tni of the liquid crystal composition of the present invention is kept high and a composition having good temperature stability is required, it is preferable that the lower limit value is low and the upper limit value is low. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value is high and the upper limit value is high.
The liquid crystal composition of the present invention particularly preferably contains 1 or 2 or more compounds represented by the general formula (N-1). The compounds represented by the general formula (N-1) include compounds represented by the following general formulae (N-1a) to (N-1 g). Wherein is derived from having-CH2The linking group represented by O-preferably contains 1 or 2 or more species of the compound represented by the general formula (N-1d) or (N-1f), and more preferably 1 or 2 or more species of the compound represented by the general formula (N-1 d).
[ solution 32]
(in the formula, RN11And RN12R in the general formula (N-1)N11And RN12Same meaning, nNa11Represents 0 or 1, nNb11Represents 1 or 2, nNc11Represents 0 or 1, nNd11Represents 1 or 2, nNe11Represents 1 or 2, nNf12Represents 1 or 2, nNg11Represents 1 or 2, ANe11Represents trans-1, 4-cyclohexylene or 1, 4-phenylene, ANg11Represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene and at least 1 represents 1, 4-cyclohexenylene, ZNe11Represents a single bond or an ethylene group, at least 1 of which is present in the molecule represents an ethylene group, and the molecule has a memoryAt a plurality of ANe11、ZNe11And/or ANg11May be the same or different. )
More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group of compounds represented by the general formulae (N-1-1) to (N-1-21).
The compound represented by the general formula (N-1-1) is the following compound.
[ solution 33]
(in the formula, RN111And RN112Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a propyl group, a pentyl group or a vinyl group. RN112Preferably 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 compounds represented by the general formula (N-1-1) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be lower. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-1) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-1.1) to (N-1-1.23), preferably a compound represented by the formulae (N-1-1.1) to (N-1-1.4), preferably a compound represented by the formulae (N-1-1.1) and (N-1-1.3).
[ chemical 34]
The compounds represented by the formulae (N-1-1.1) to (N-1-1.22) may be used alone or in combination. The lower limit value of the content of the compound represented by the formulae (N-1-1.1) to (N-1-1.22) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-2) is the following compound.
[ solution 35]
(in the formula, RN121And RN122Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group or a pentyl group. RN122Preferably 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, preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.
The compounds represented by the general formula (N-1-2) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When importance is attached to improvement of Δ ∈, it is preferable to set the content higher, when importance is attached to solubility at low temperature, it is more effective, and when importance is attached to TNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-2) is preferably 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 37 mass%, 40 mass%, 42 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 48 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-2) is preferablyThe compounds selected from the group consisting of the compounds represented by the formulae (N-1-2.1) to (N-1-2.22) are preferably the compounds represented by the formulae (N-1-2.3) to (N-1-2.7), the formulae (N-1-2.10), the formulae (N-1-2.11), the formulae (N-1-2.13) and (N-1-2.20), and when an improvement in Delta epsilon is important, the compounds represented by the formulae (N-1-2.3) to (N-1-2.7) are preferably the compounds represented by the formulae (N-1-2.3) to (N-1-2.7) in which T is importantNIThe compound represented by the formula (N-1-2.10), the formula (N-1-2.11) or the formula (N-1-2.13) is preferable for the improvement of (4), and the compound represented by the formula (N-1-2.20) is preferable for the improvement of the response speed.
[ solution 36]
The compounds represented by the formulae (N-1-2.1) to (N-1-2.22) may be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the above content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-3) is the following compound.
[ solution 37]
(in the formula, RN131And RN132Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms,ethyl, propyl or butyl are preferred. RN132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-3) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-3) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-3) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-3.1) to (N-1-3.21), preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-3.1) to (N-1-3.7) and (N-1-3.21), preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-3.1), (N-1-3.2), (N-1-3.3), (N-1-3.4) and (N-1-3.6).
[ solution 38]
The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) may be used alone or in combination, and preferably a combination of the formulae (N-1-3.1) and (N-1-3.2), a combination of 2 or 3 selected from the formulae (N-1-3.3), (N-1-3.4) and (N-1-3.6). The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-4) is the following compound.
[ solution 39]
(in the formula, RN141And RN142Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN141And RN142Each 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, and preferably a methyl group, a propyl group, an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-4) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be lower. Furthermore, the characteristics of dropping marks and screen burning are improvedIn the case of improvement, the range of the content is preferably set to be intermediate.
The lower limit of the content of the compound represented by the general formula (N-1-4) is preferably 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-4) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-4.1) to (N-1-4.14), preferably a compound represented by the formulae (N-1-4.1) to (N-1-4.4), preferably a compound represented by the formulae (N-1-4.1), (N-1-4.2) and (N-1-4.4).
[ solution 40]
The compounds represented by the formulae (N-1-4.1) to (N-1-4.14) may be used alone or in combination. The lower limit of the content of these compounds is preferably 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-5) is the following compound.
[ solution 41]
(in the formula, RN151And RN152Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN151And RN152Each 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, and preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-5) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When importance is attached to improvement of Δ ∈, it is preferable to set the content higher, when importance is attached to solubility at low temperature, it is more effective, and when importance is attached to TNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-5) is preferably 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-5.1) to (N-1-5.6), preferably compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4).
[ solution 42]
The compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4) may be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-10) is the following compound.
[ solution 43]
(in the formula, RN1101And RN1102Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1101Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
RN1102The alkyl group having 1 to 5 carbon atoms, the alkenyl group having 4 to 5 carbon atoms or the alkoxy group having 1 to 4 carbon atoms is preferable, and among them, the alkoxy group having 1 to 4 carbon atoms is preferable. RN1102When the alkoxy group is represented, the 2, 3-difluoro-1, 4-phenylene group in the general formula (N-1-10) is bonded to a linking group (-CH)2Oxygen atom of O-) and R-N1102The structure in which the oxygen atoms of the alkoxy groups are bonded is shown. The compound having such a structure exhibits negative dielectric anisotropy (Δ ∈), and the absolute value of the dielectric anisotropy can exhibit a large value. Therefore, in particular, a liquid crystal composition having negative dielectric anisotropy can be improved in Δ ∈ by including the above compound. In the present invention, by using the compound having the above structure in combination with the light stabilizer represented by the above general formula (H), the photodegradation of the compound having the above structure is suppressed, and the dielectric anisotropy exhibited by the compound is utilizedA liquid crystal composition exhibiting a high Δ ∈ can be prepared. In the C1-4 alkoxy group, RN1102More preferably ethoxy, propoxy or butoxy.
The compounds represented by the general formula (N-1-10) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be lower. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-10) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-10) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-10.1) to (N-1-10.14), preferably a compound represented by the formulae (N-1-10.1) to (N-1-10.5), preferably a compound represented by the formulae (N-1-10.1) and (N-1-10.2).
[ solution 44]
The compounds represented by the formulae (N-1-10.1) and (N-1-10.2) may be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-11) is the following compound.
[ solution 45]
(in the formula, RN1111And RN1112Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
RN1112The alkyl group having 1 to 5 carbon atoms, the alkenyl group having 4 to 5 carbon atoms or the alkoxy group having 1 to 4 carbon atoms is preferable, and among them, the alkoxy group having 1 to 4 carbon atoms is preferable. For the reason, R in the above general formula (N-1-10)N1102The reasons why alkoxy groups are preferred are the same. In the C1-4 alkoxy group, RN1112More preferably ethoxy, propoxy or butoxy.
The compounds represented by the general formula (N-1-11) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When importance is attached to improvement of Δ ∈, it is preferable to set the content higher, when importance is attached to solubility at low temperature, it is more effective, and when importance is attached to TNIThe effect is good when the content is set to be higher.Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-11) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-11) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-11.1) to (N-1-11.14), preferably a compound represented by the formulae (N-1-11.2) and (N-1-11.4).
[ solution 46]
The compounds represented by the formulae (N-1-11.2) and (N-1-11.4) may be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-12) is the following compound.
[ solution 47]
(in the formula, RN1121And RN1122Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used.)
RN1121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1122Preferably 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 compounds represented by the general formula (N-1-12) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be lower. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-12) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-13) is the following compound.
[ solution 48]
(in the formula, RN1131And RN1132Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1132Preferably 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 kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-13) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-14) is the following compound.
[ solution 49]
(in the formula, RN1141And RN1142Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1141Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1142Preferably C1-C5 alkaneThe group, alkenyl group having 4 to 5 carbon atoms or alkoxy group having 1 to 4 carbon atoms, preferably ethoxy group, propoxy group or butoxy group.
The compounds represented by the general formula (N-1-14) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be lower. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the general formula (N-1-14) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-15) is the following compound.
[ solution 50]
(in the formula, RN1151And RN1152Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1151Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1152Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a C1 to 4 alkoxy groups, preferably ethoxy, propoxy or butoxy groups.
The compounds represented by the general formula (N-1-15) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-15) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formula (N-1-16) are the following compounds.
[ solution 51]
(in the formula, RN1161And RN1162Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1161Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1162Preferably 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, preferably an ethoxy group, a propoxy group orButoxy group.
The compounds represented by the general formula (N-1-16) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-16) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formula (N-1-17) are the following compounds.
[ solution 52]
(in the formula, RN1171And RN1172Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1171Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1172Preferably 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 compounds represented by the general formula (N-1-17) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-17) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The lower limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formula (N-1-18) are the following compounds.
[ Hua 53]
(in the formula, RN1181And RN1182Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1181Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a methyl group, an ethyl group, a propyl group or a butyl group. RN1182Preferably 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 compounds represented by the general formula (N-1-18) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-18) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-18) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-18.1) to (N-1-18.5), preferably a compound represented by the formulae (N-1-18.1) to (N-1-18.3), preferably a compound represented by the formulae (N-1-18.2) and (N-1-18.3).
[ solution 54]
The compound represented by the general formula (N-1-20) is the following compound.
[ solution 55]
(in the formula, RN1201And RN1202Each independently representsR in the general formula (N-1)N11And RN12The same meaning is used. )
RN1201And RN1202Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-20) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-20) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-21) is the following compound.
[ solution 56]
(in the formula, RN1211And RN1212Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1211And RN1212Are each independently preferably a carbon atomAn alkyl group having a number of 1 to 5 or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-21) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-21) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-22) is the following compound.
[ solution 57]
(in the formula, RN1221And RN1222Each independently represents R in the general formula (N-1)N11And RN12The same meaning is used. )
RN1221And RN1222Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-22) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the improvement of Δ ∈ is emphasized, it is preferable to set the content higher, when the solubility at low temperature is emphasized, it is more effective, and when T is emphasizedNIThe effect is good when the content is set to be higher. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (N-1-21) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, or 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-22) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-22.1) to (N-1-22.12), preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.5), preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.4).
[ solution 58]
[2] Second embodiment of the Compound represented by the general formula (II)
A second embodiment of the compound represented by the general formula (II) (hereinafter, may be referred to as a second embodiment compound) is a liquid crystal compound having a positive dielectric anisotropy (Δ ∈). The compound of the second mode is preferably larger than 2.
Examples of the compound of the second embodiment include compounds selected from the group of compounds represented by the following general formula (M) and general formula (K).
[ chemical 59]
(in the formula, RM1And RK1Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
nM1and nK1Each independently represents 0, 1,2,3 or 4,
AM1and AM2And AK1And AK2Each independently represents a group selected from the group consisting of,
(a)1, 4-cyclohexylene (1-CH present in the radical)2-or 2 or more-CH not adjacent2-may be substituted by-O-or-S-. ) And
(b)1, 4-phenylene (1-CH-or nonadjacent 2 or more-CH-present in the radical may be substituted by-N)
The hydrogen atoms on the above-mentioned group (a) and group (b) may each independently be substituted by a cyano group, a fluorine atom or a chlorine atom,
ZM1and ZM2And ZK1And ZK2Each independently represents a single bond, -CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-, -COO-, -OCO-or-C ≡ C-,
n in the general formula (M)M1Is 2,3 or 4 and AM2And ZM1When there are plural, plural AM2And ZM1Each of which may be the same or different,
n in the general formula (K)K1Is 2,3 or 4 and AK2And ZK1When there are plural, plural AK2And ZK1Each of which may be the same or different,
XM1and XM3And XK1And XK3Each independently represents a hydrogen atom, a chlorine atom or a fluorine atom,
XM2and XK2Each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2,2, 2-trifluoroethyl group. )
When the liquid crystal composition of the present invention has a positive value of dielectric anisotropy (. DELTA.. di-elect cons.) at 25 ℃, the liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formula (M) and the general formula (K).
The liquid crystal composition of the present invention preferably contains 1 or 2 or more kinds of Z selected from the group consisting of Z in the general formula (M)M1And ZM2At least 1 of (a) represents-CH2O-compound, and Z in the general formula (K)K1And ZK2At least 1 of (a) represents-CH2A compound of the group consisting of compounds of O-. This is because these compounds have-CH in their molecular structure2A linking group represented by O-can realize the above-mentioned structure having a-CH group2The effect of using a compound having a linking group represented by O-in combination with a light stabilizer represented by the general formula (H).
In the liquid crystal composition of the present invention, the total content of the compounds selected from the group of compounds represented by the general formulae (M) and (K) can be appropriately adjusted depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit value of the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention, and the upper limit value of the total content is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the viscosity of the liquid crystal composition of the present invention is kept low and a composition having a high response speed is required, the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably set to a lower limit and a lower upper limit. When Tni of the liquid crystal composition of the present invention is kept high and a composition having good temperature stability is required, the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably set to a lower limit and a lower upper limit. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably such that the lower limit value is higher and the upper limit value is higher.
The compounds represented by the general formula (M) and the general formula (K) will be described below.
< Compound represented by the general formula (M) >
In the general formula (M), RM1The alkyl group having 1 to 8 carbon atoms, the alkoxy group having 1 to 8 carbon atoms, the alkenyl group having 2 to 8 carbon atoms or the alkenyloxy group having 2 to 8 carbon atoms is preferable, the alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 5 carbon atoms, the alkenyl group having 2 to 5 carbon atoms or the alkenyloxy group having 2 to 5 carbon atoms is preferable, the alkyl group having 1 to 5 carbon atoms or the alkenyl group having 2 to 5 carbon atoms is more preferable, the alkyl group having 2 to 5 carbon atoms or the alkenyl group having 2 to 3 carbon atoms is further preferable, and the alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
In addition, RM1The alkyl group is preferable when importance is attached to reliability, and the alkenyl group is preferable when importance is attached to reduction in viscosity.
In addition, when R isM1Attached to AM1When the ring structure of (A) is phenyl (aromatic), RM1Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a carbon number of 4 to 5. On the other hand, when RM1Attached to AM1When the ring structure (C) is a saturated ring structure such as cyclohexane, pyran or dioxane, R isM1Preferably a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atomsA straight chain alkenyl group having 2 to 5 carbon atoms.
With respect to RM1In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably selected from the group represented by any one of the formulae (R1) to (R5) described in the section "[ 1] first embodiment of the compound represented by the general formula (II)".
When an increase of Δ n is required, AM1And AM2Each independently preferably aromatic. In addition, to improve response speed, AM1And AM2Each independently preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Among them AM1And AM2Each independently more preferably represents any one of the following structures.
[ solution 60]
Further, AM1And AM2Each independently preferably represents any one of the following structures.
[ solution 61]
ZM1And ZM2Each independently preferably represents-CH2O-、-CF2O-、-CH2CH2-、-CF2CF2-or a single bond, further preferably-CF2O-、-CH2CH2-or a single bond, particularly preferably-CF2O-or a single bond.
nM1Preferably represents 0, 1,2 or 3, preferably represents 0, 1 or 2. When emphasis is placed on the improvement of Δ ε, nM1Preferably represents 0 or 1, n when the emphasis is placed on TniM1Preferably represents 1 or 2.
The kind of the compound that can be combined is not particularly limited, and it is used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, and 3 as one embodiment of the present invention. In other embodiments of the present invention, the number of the cells is 4, 5, 6, 7 or more.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (M) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the general formula (M) is preferably 0 mass%, 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the general formula (M) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the viscosity of the liquid crystal composition of the present invention is kept low and a composition having a high response speed is required, the content of the compound represented by the general formula (M) is preferably set to a lower limit and a lower upper limit. When Tni of the liquid crystal composition of the present invention is kept high and a composition having good temperature stability is required, the content of the compound represented by the general formula (M) is preferably set to a lower limit and a lower upper limit. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (M) is preferably such that the lower limit is higher and the upper limit is higher.
The liquid crystal compound represented by the general formula (M) is preferably a compound selected from the group consisting of compounds represented by the following general formula (M-1) and compounds represented by the following general formula (M-2).
[ solution 62]
(in the formula, R31Represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,
X31and X32Each independently represents a hydrogen atom or a fluorine atom,
Y31represents a fluorine atom or OCF3，
M31To M33Each independently represents trans-1, 4-cyclohexylene or 1, 4-phenylene, 1 or 2-CH groups in the trans-1, 4-cyclohexylene2May be substituted by-O-in such a way that the oxygen atoms are not directly adjacent, 1 or 2 hydrogen atoms in the phenylene group being substituted by fluorine atoms,
n31and n32Each independently represents 0, 1 or 2,
n31+n32represents 1,2 or 3. )
Among these, the liquid crystal composition of the present invention preferably contains 1 or more compounds represented by the general formula (M-2). This is because the compound represented by the general formula (M-2) has a-CH-linkage in its molecular structure2The structure in which 2 ring structures adjacent to each other are connected to each other through a linker represented by O-can be realized by having the structure described above as having-CH2The effect of using a compound having a linking group represented by O-in combination with a light stabilizer represented by the general formula (H).
The liquid crystal compound represented by the general formula (M-1) is preferably a compound represented by the following general formula (M-1-a) to (M-1-f).
[ solution 63]
(in the formula, R31、X31、X32And Y31Respectively represent R in the general formula (M)31、X31、X32And Y31Same meaning as X34To X39Each independently represents a hydrogen atom or a fluorine atom. )
Specifically, the liquid crystal compound represented by the general formula (M-2) is preferably a compound represented by the following general formula (M-2-a) to general formula (M-2-n).
[ solution 64]
[ solution 65]
(in the formula, R31、X31、X32And Y31Respectively represent R in the general formula (M)31、X31、X32And Y31Same meaning as X34To X39Each independently represents a hydrogen atom or a fluorine atom. )
The liquid crystal compound represented by the general formula (M) is preferably a compound represented by the following general formula (M-3) to (M-26).
[ solution 66]
[ solution 67]
(in the formula, R31、X31、X32And Y31Respectively represent R in the general formula (M)31、X31、X32And Y31Same meaning as X34To X39Each independently representA hydrogen atom or a fluorine atom. )
<2> Compound represented by the general formula (K)
In the general formula (K), RK1The alkyl group having 1 to 8 carbon atoms, the alkoxy group having 1 to 8 carbon atoms, the alkenyl group having 2 to 8 carbon atoms or the alkenyloxy group having 2 to 8 carbon atoms is preferable, the alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 5 carbon atoms, the alkenyl group having 2 to 5 carbon atoms or the alkenyloxy group having 2 to 5 carbon atoms is preferable, the alkyl group having 1 to 5 carbon atoms or the alkenyl group having 2 to 5 carbon atoms is more preferable, the alkyl group having 2 to 5 carbon atoms or the alkenyl group having 2 to 3 carbon atoms is further preferable, and the alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
RK1The alkyl group is preferable when importance is attached to reliability, and the alkenyl group is preferable when importance is attached to reduction in viscosity.
RK1Attached to AK1When the ring structure of (A) is phenyl (aromatic), RK1Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a carbon number of 4 to 5. In another aspect, RK1Attached to AK1When the ring structure (C) is a saturated ring structure such as cyclohexane, pyran or dioxane, R isK1Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a straight chain of 2 to 5 carbon atoms.
For stabilizing the nematic phase, RK1The total of the carbon atoms and the oxygen atoms is preferably 5 or less, in which case RK1Preferably straight chain.
RK1When an alkenyl group is represented, the alkenyl group is preferably selected from the group consisting of "[ 1] mentioned above]A group represented by any one of the formulae (R1) to (R5) described in the first embodiment "of the compound represented by the general formula (II).
When an increase of Δ n is required, AK1And AK2Each independently preferably aromatic. In addition, to improve response speed, AK1And AK2Each independently preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1,4-cyclohexenylene, 1, 4-bicyclo [2.2.2]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Among them AK1And AK2Each independently preferably represents any one of the following structures.
[ solution 68]
Further, AK1And AK2Each independently preferably represents any one of the following structures.
[ solution 69]
ZK1And ZK2Each independently preferably represents-CH2O-、-CF2O-、-CH2CH2-、-CF2CF2-or a single bond, further preferably-CF2O-、-CH2CH2-or a single bond, particularly preferably-CF2O-or a single bond.
nK1Preferably represents 0, 1,2 or 3, preferably 0, 1 or 2. When emphasis is placed on the improvement of Δ ε, nK1Preferably represents 0 or 1, n when the emphasis is placed on TniK1Preferably represents 1 or 2.
The kind of the compound that can be combined is not particularly limited, and it is used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kinds of the compounds used are, for example, 1,2,3,4, 5, 6, 7 or more.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (K) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the general formula (K) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the general formula (K) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the viscosity of the liquid crystal composition of the present invention is kept low and a composition having a high response speed is required, the content of the compound represented by the general formula (K) is preferably set to a lower limit and a lower upper limit. When Tni of the liquid crystal composition of the present invention is kept high and a composition having good temperature stability is required, the content of the compound represented by the general formula (K) is preferably set to a lower limit and a lower upper limit. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (K) is preferably such that the lower limit is higher and the upper limit is higher.
The liquid crystal compound represented by the general formula (K) is preferably a compound selected from the group consisting of compounds represented by the following general formulae (K-1) and (K-2).
[ solution 70]
(in the formula, R41Represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,
X41and X42Each independently represents a hydrogen atom or a fluorine atom,
Y41represents a fluorine atom or OCF3，
M41To M43Each independently represents trans-1, 4-cyclohexylene or 1, 4-phenylene, 1 or 2-CH groups in the trans-1, 4-cyclohexylene2May be directly not adjacent to an oxygen atomSubstituted by-O-, in which 1 or 2 hydrogen atoms may be replaced by fluorine atoms,
n41and n42Each independently represents 0, 1 or 2, n41+n42Represents 1,2 or 3. )
Among these, the liquid crystal composition of the present invention preferably contains 1 or more compounds represented by the general formula (K-2). This is because the compound represented by the general formula (K-2) has a-CH-linkage in its molecular structure2The structure in which 2 ring structures adjacent to each other are connected to each other through a linker represented by O-can be realized by having the structure described above as having-CH2The effect of using a compound having a linking group represented by O-in combination with a light stabilizer represented by the general formula (H).
The liquid crystal compound represented by the general formula (K-1) is preferably a compound represented by the following general formula (K-1-a) to general formula (K-1-d).
[ solution 71]
(in the formula, R41、X41、X42And Y41R in the general formula (K)41、X41、X42And Y41Same meaning as X44～X49Each independently represents a hydrogen atom or a fluorine atom. )
Specifically, the liquid crystal compounds represented by the general formula (K-2) are preferably compounds represented by the following general formulae (K-2-a) to (K-2-g).
[ chemical formula 72]
(in the formula, R41、X41、X42And Y41R in the general formula (K)41、X41、X42And Y41Same meaning as X44～X49Each independently represents a hydrogen atom or a fluorine atom. )
The liquid crystal compound represented by the general formula (K) is preferably represented by the following general formulae (K-3) to (K-5).
[ solution 73]
(in the formula, R41、X41、X42And Y41R in the general formula (K)41、X41、X42And Y41Same meaning as X44～X49Each independently represents a hydrogen atom or a fluorine atom. )
[3] A third formula of the compound represented by the general formula (II)
A third embodiment (hereinafter referred to as a compound of the third embodiment) of the compound represented by the general formula (II) is a compound having a dielectric anisotropy of about 0, so-called a nonpolar liquid crystal compound. The value of the dielectric anisotropy (. DELTA.. di-elect cons.) at 25 ℃ of the compound of the third embodiment is preferably in the range of-2 to 2.
The compound of the third embodiment may be a compound represented by the following general formula (L). That is, the liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (L).
[ chemical formula 74]
(in the formula, RL1And RL2Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
nL1represents 0, 1,2 or 3,
AL1、AL2and AL3Each independently represents a group selected from the group consisting of,
(a)1, 4-cyclohexylene radical (present in this radical)1-CH of2-or 2 or more-CH not adjacent2-may be substituted by-O-. ) And
(b)1, 4-phenylene (1-CH-or nonadjacent 2 or more-CH-present in the radical may be substituted by-N)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)
The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
ZL1and ZL2Each independently represents a single bond, -CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
nL1is 2 or 3 or AL2When there are plural, they may be the same or different, and nL1Is 2 or 3 and thus ZL2When a plurality of them exist, they may be the same or different.
Wherein compounds represented by the general formulae (M) and (K) and compounds represented by the general formulae (N-1), (N-2) and (N-3) are excluded. )
The compound represented by the general formula (L) corresponds to a compound having a substantially neutral dielectric property (the value of. DELTA. epsilon. at 25 ℃ is-2 or more and 2 or less). Therefore, the number of polar groups such as halogen contained in the molecule of the compound represented by the general formula (L) is preferably 2 or less, preferably 1 or less, and preferably no polar groups such as halogen are contained.
The compounds represented by the general formula (L) may be used alone or in combination. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with desired performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kinds of the compounds used are, for example, 1,2,3,4, 5, 6, 7, 8, 9, 10 or more.
The content of the compound represented by the general formula (L) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like. The lower limit of the content of the compound represented by the general formula (L) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the general formula (L) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the viscosity of the liquid crystal composition of the present invention is kept low and a liquid crystal composition having a high response speed is required, the content of the compound represented by the general formula (L) is preferably high at the lower limit and high at the upper limit. When Tni of the liquid crystal composition of the present invention is kept high and a liquid crystal composition having good temperature stability is required, the content of the compound represented by the general formula (L) is preferably high at the lower limit and high at the upper limit. When the dielectric anisotropy is to be increased in order to keep the driving voltage low, the content of the compound represented by the general formula (L) is preferably low in the lower limit and low in the upper limit.
RL1And RL2In order to emphasize reliability, it is preferable that all of them are alkyl groups, in order to emphasize reduction of volatility of the compound, it is preferable that at least one of them is an alkoxy group, and in order to emphasize reduction of viscosity, it is preferable that at least one of them is an alkenyl group.
RL1And RL2At A to which they are attachedL1And AL3When the cyclic structure(s) is (are) phenyl (aromatic), each independently preferably is a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. In addition, RL1And RL2At A to which they are attachedL1And AL3When the cyclic structure (C) is a saturated cyclic structure such as cyclohexane, pyran or dioxane, the cyclic structure (C) is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a linear alkoxy group, each of which is independent of the otherAn alkenyl group having 2 to 5 carbon atoms. In addition, R is added to stabilize the nematic phaseL1And RL2Independently of each other, the total of carbon atoms and oxygen atoms is preferably 5 or less, and in this case, it is preferably linear.
The alkenyl group is preferably selected from the group represented by any one of the formulae (R1) to (R5) described in the section "[ 1] first embodiment of the compound represented by the general formula (II)".
nL1When importance is attached to the response speed, 0 is preferable, 2 or 3 is preferable for improving the upper limit temperature of the nematic phase, and 1 is preferable for achieving the balance therebetween. In addition, n is preferably used in order to satisfy the characteristics required as a liquid crystal compositionL1Combinations of compounds represented by the general formula (L) of different values.
AL1、AL2And AL3When it is desired to increase Δ n, it is preferably aromatic, and in order to improve the response speed, it is preferably aliphatic, and each independently preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ]]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Among them AL1、AL2And AL3Each independently more preferably represents the following structure, more preferably represents trans-1, 4-cyclohexylene or 1, 4-phenylene.
[ solution 75]
ZL1And ZL2When importance is attached to the response speed, a single bond is preferable.
The number of halogen atoms present in the molecule of the compound represented by the general formula (L) is preferably 0, 1,2 or 3, more preferably 0 or 1, and when importance is attached to compatibility with other liquid crystal molecules, 1 is preferred.
In the liquid crystal composition of the present invention, it is preferable that the compound represented by the general formula (L) contains 1 or 2 or more compounds represented by the general formula (L-1A).
[ 76]
(in the above general formula (L-1A), Ri1AAnd Ri2AEach independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-, Ri1AAnd R i2A1 or non-adjacent 2 or more-CH in the alkyl group2Each independently may be substituted by-CH ═ CH-. )
In the compound represented by the general formula (L-1A), Ri1AAnd Ri2AAt least one of them represents 1 or non-adjacent 2 or more-CH in the alkyl group2-each independently substituted with-CH ═ CH-. That is, in the compound represented by the general formula (L-1A), Ri1AAnd Ri2AAt least one of the above groups represents an alkenyl group having 2 to 8 carbon atoms.
It is known that the compound represented by the general formula (L-1A) has an alkenyl group and thus can reduce the viscosity and response time of a liquid crystal composition, but on the other hand, reduces reliability and stability. It is known that particularly a compound having an alkenyl group is deteriorated when irradiated with UV to easily generate an impurity, and reduction of VHR is caused by the impurity. On the other hand, since the liquid crystal composition of the present invention contains the light stabilizer represented by the general formula (H), impurities generated by the light deterioration of the compound represented by the general formula (L-1A) are trapped by the light stabilizer represented by the general formula (H), so that the decrease in reliability and stability can be suppressed, and the content of the general formula (L-1A) can be increased to reduce the viscosity and response time. Thus, the liquid crystal composition of the present invention can exhibit high Δ ∈ and low viscosity, and realize high-speed response and high stability.
Among them, Ri1AAnd Ri2AAt least one of the above is preferably represented by any one of the above-described formulae (R1) to (R5). In addition, Ri1AAnd Ri2AIn (1) canOnly one of which is alkenyl, or Ri1AAnd Ri2ABoth are alkenyl groups. Ri1AAnd Ri2AWhen both are alkenyl, Ri1AAnd Ri2AMay be the same or different.
Ri1AAnd Ri2AAt least one of them particularly preferably represents an alkenyl group having 2 to 5 carbon atoms.
The liquid crystal composition of the present invention preferably contains at least 1 compound represented by the general formula (L-1A). The composition may contain 2 or more of them in combination. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kinds of the compounds used are, for example, 1,2,3,4, 5 or more.
The lower limit of the content of the compound represented by the general formula (L-1A) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 15 mass%, 20 mass%, 25 mass%, 30 mass%, 35 mass%, 40 mass%, 45 mass%, 50 mass%, 55 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-1).
[ solution 77]
(in the formula, RL12ARepresents the same meaning as in the general formula (L-1A). )
The compound represented by the general formula (L-1A-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1A-1.1) to (L-1A-1.3), preferably a compound represented by the formula (L-1A-1.2) or (L-1A-1.3), and particularly preferably a compound represented by the formula (L-1A-1.3).
[ solution 78]
The lower limit of the preferable content of the compound represented by the formula (L-1A-1) is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention. Among these, the compound represented by the formula (L-1A-3) is preferably contained within the range between the lower limit and the upper limit.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-2).
[ solution 79]
(in the formula, RL12ARepresents the same meaning as in the general formula (L-1A). )
The lower limit of the content of the compound represented by the formula (L-1A-2) is preferably 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1A-2.1) to (L-1A-2.4), and is preferably a compound represented by the formulae (L-1A-2.2) to (L-1A-2.4). In particular, the compound represented by the formula (L-1A-2.2) is preferable because it improves the response speed of the liquid crystal composition of the present invention. In addition, when higher Tni is required than the response speed, it is preferable to use a compound represented by the formula (L-1A-2.3) or the formula (L-1A-2.4). The content of the compound represented by the formula (L-1A-2.3) or the formula (L-1A-2.4) is not preferably 30% by mass or more in order to improve the solubility at low temperatures.
[ solution 80]
When the liquid crystal composition of the present invention contains the compound represented by the formula (L-1A-2.2), the lower limit of the content of the compound represented by the formula (L-1A-2.2) is preferably 10 mass%, 15 mass%, 18 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 38 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention preferably contains both the compound represented by the formula (L-1A-1.3) and the compound represented by the formula (L-1A-2.2). The lower limit of the content of the compound represented by the formula (L-1A-1.3) and the compound represented by the formula (L-1A-2.2) is preferably 10 mass%, 15 mass%, 20 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group consisting of compounds represented by the general formulae (L-1A-4) and (L-1A-5).
[ solution 81]
(in the formula, RL12ARepresents the same meaning as in the general formula (L-1A). )
In the general formulae (L-1A-4) and (L-1A-5), RL12AThe alkyl group having 1 to 8 carbon atoms, the alkoxy group having 1 to 8 carbon atoms or the alkenyl group having 2 to 8 carbon atoms is preferable, and the alkyl group having 1 to 5 carbon atoms is preferable to be linear, the alkoxy group having 1 to 4 carbon atoms is preferable to be linear, and the alkenyl group having 2 to 5 carbon atoms is preferable to be linear.
The lower limit of the content of the compound represented by the formula (L-1A-4) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, or 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The lower limit of the content of the compound represented by the formula (L-1A-5) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formulae (L-1A-4) and (L-1A-5) are preferably compounds selected from the group of compounds represented by the formulae (L-1A-4.1) to (L-1A-5.3), and are preferably compounds represented by the formula (L-1A-4.2) or the formula (L-1A-5.2).
[ solution 82]
When the liquid crystal composition of the present invention contains the compound represented by the formula (L-1A-4.2), the lower limit of the content of the compound represented by the formula (L-1A-4.2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, or 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-6).
[ solution 83]
(in the formula, RL17And RL18Each independently represents a methyl group or a hydrogen atom. )
The lower limit of the content of the compound represented by the formula (L-1A-6) is preferably 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A-6) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1A-6.1) to (L-1A-6.3).
[ solution 84]
In addition, in the liquid crystal composition of the present invention, it is preferable that the compound represented by the general formula (L) further contains 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formula (L-1B) and the compounds represented by the general formulae (L-2) to (L-7) in addition to the compound represented by the general formula (L-1A).
The compound represented by the general formula (L-1B) is the following compound.
[ solution 85]
(in the formula, RL11BAnd RL12BEach independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-C.ident.C-, -O-, -CO-, -COO-or-OCO-. )
A compound represented by the general formula (L-1B) in RL11BAnd RL12BOne or both of them do not represent an alkenyl group, and is different from the compound represented by the general formula (L-1A).
RL11BAnd RL12BPreferably a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
The liquid crystal composition of the present invention may contain 1 kind of the compound represented by the general formula (L-1B), or may contain 2 or more kinds in combination. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kinds of the compounds used are, for example, 1,2,3,4, 5 or more.
The lower limit of the content of the compound represented by the formula (L-1B) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 30 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 37 mass%, 35 mass%, 33 mass%, 30 mass%, 27 mass%, 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1B) is preferably a compound selected from the group of compounds represented by the formulae (L-1B-1) to (L-1B-13), and is preferably a compound selected from the group of compounds represented by the formulae (L-1B-1), (L-1B-3) and (L-1B-4). In particular, the compound represented by the formula (L-1B-1) is preferable because it improves the response speed of the liquid crystal composition of the present invention. In addition, when higher Tni is required than the response speed, it is preferable to use a compound selected from the group of compounds represented by the formula (L-1B-3), the formula (L-1B-4), the formula (L-1B-11) and the formula (L-1B-12). In order to improve the solubility at low temperatures, the total content of the compounds represented by the formulae (L-1B-3), (L-1B-4), (L-1B-11) and (L-1B-13) is not preferably 20% by mass or more.
[ solution 86]
When the liquid crystal composition of the present invention contains the compound represented by formula (L-1B-1), the lower limit of the content of the compound represented by formula (L-1B-1) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, or 20 mass% of the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention preferably contains 2 or more compounds selected from the group of compounds represented by formula (L-1A-1.3), formula (L-1A-2.2), formula (L-1B-1), formula (L-1B-3), formula (L-1B-4), formula (L-1B-11) and formula (L-1B-12) in combination. Further, the liquid crystal composition of the present invention preferably contains 2 or more compounds selected from the group consisting of the compounds represented by the formula (L-1A-1.3), the formula (L-1A-2.2), the formula (L-1B-1), the formula (L-1B-3), the formula (L-1B-4) and the formula (L-1A-4.2) in combination. The lower limit of the total content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 80 mass%, 70 mass%, 60 mass%, 50 mass%, 45 mass%, 40 mass%, 37 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When importance is attached to the reliability of the liquid crystal composition, it is preferable to combine 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1B-1), (L-1B-3) and (L-1B-4). When importance is attached to the response speed of the liquid crystal composition, it is preferable to combine 2 or more compounds selected from the group consisting of the compounds represented by the formula (L-1A-1.3) and the formula (L-1A-2.2).
The liquid crystal composition of the present invention preferably contains 1 or more compounds represented by the general formula (L-1A) and 1 or more compounds represented by the general formula (L-1B). The lower limit of the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 15 mass%, 20 mass%, 25 mass%, 30 mass%, 35 mass%, 40 mass%, 45 mass%, 50 mass%, 55 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the above content is preferably 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the viscosity of the liquid crystal composition of the present invention is kept low and a composition having a high response speed is required, it is preferable that the lower limit value and the upper limit value of the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) are high. When the Tni of the liquid crystal composition of the present invention is kept high and a composition having good temperature stability is required, it is preferable that the lower limit value and the upper limit value of the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) are centered. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value and the upper limit value of the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) are low.
The compound represented by the general formula (L-2) is the following compound.
[ solution 87]
(in the formula, RL21And RL22Each independently represents R in the general formula (L)L1And RL2The same meaning is used. )
RL21Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. In addition, RL22Preferably 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 unsaturated bond of the alkenyl group is not directly bonded to benzene.
The compounds represented by the general formula (L-2) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
When the solubility at low temperature is regarded as important, the effect is good if the content is set to be higher, whereas when the response speed is regarded as important, the effect is good if the content is set to be lower. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The lower limit of the content of the compound represented by the formula (L-2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-2.1) to (L-2.6), and is preferably a compound represented by the formulae (L-2.1), (L-2.3), (L-2.4) and (L-2.6).
[ solution 88]
The compound represented by the general formula (L-3) is the following compound.
[ solution 89]
(in the formula, RL31And RL32Each independently represents R in the general formula (L)L1And RL2The same meaning is used. )
RL31And RL32Each 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. Further, it is preferable that the unsaturated bond of the alkenyl group is not directly bonded to benzene.
The compounds represented by the general formula (L-3) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
The lower limit of the content of the compound represented by the formula (L-3) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
To obtain a height ofWhen the birefringence is high, the effect is good if the content is set to be high, whereas when high T is importantNIWhen the content is set to be lower, the effect is good. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.
The compound represented by the general formula (L-3) is preferably a compound selected from the group of compounds represented by the formulae (L-3.1) to (L-3.7), and is preferably a compound represented by the formulae (L-3.2) to (L-3.5).
[ solution 90]
The compound represented by the general formula (L-4) is the following compound.
[ solution 91]
(in the formula, RL41And RL42Each independently represents R in the general formula (L)L1And RL2The same meaning is used. )
RL41Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, RL42Preferably 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. Preferably, the unsaturated bond of the alkenyl group is not directly connected to benzene.
The compounds represented by the general formula (L-4) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-4) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the formula (L-4) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formula (L-4) are preferably, for example, compounds represented by the formulae (L-4.1) to (L-4.3).
[ solution 92]
The compound represented by the formula (L-4.1), the compound represented by the formula (L-4.2), both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2), or all of the compounds represented by the formulae (L-4.1) to (L-4.3) may be contained in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The lower limit of the content of the compound represented by the formula (L-4.1) or the formula (L-4.2) is preferably 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass% with respect to the total amount of the liquid crystal composition of the present invention, and the upper limit thereof is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%.
When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the lower limit of the total content of both compounds is preferably 15 mass%, 19 mass%, 24 mass%, or 30 mass% with respect to the total amount of the liquid crystal composition of the present invention, and the upper limit of the total content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, or 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by the formula (L-4.4) to the formula (L-4.6), and is preferably a compound represented by the formula (L-4.4).
[ solution 93]
The compound represented by the formula (L-4.4), the compound represented by the formula (L-4.5), or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like.
The lower limit of the content of the compound represented by the formula (L-4.4) or the formula (L-4.5) is preferably 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the lower limit of the total content of both the compounds is preferably 15 mass%, 19 mass%, 24 mass%, or 30 mass% with respect to the total amount of the liquid crystal composition of the present invention, and the upper limit of the total content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, or 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.7) to (L-4.10), and particularly preferably a compound represented by the formula (L-4.9).
[ solution 94]
The compound represented by the general formula (L-5) is the following compound.
[ solution 95]
(in the formula, RL51And RL52Each independently represents R in the general formula (L)L1And RL2The same meaning is used. )
RL51Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, RL52Preferably 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. Preferably, the unsaturated bond of the alkenyl group is not directly connected to benzene.
The compounds represented by the general formula (L-5) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-5) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the formula (L-5) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and particularly preferably a compound represented by the formula (L-5.1).
[ solution 96]
The lower limit of the content of the compound represented by the formula (L-5.1) or the formula (L-5.2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, or 7 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).
[ solution 97]
The lower limit of the content of the compound represented by the formula (L-5.3) or the formula (L-5.4) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, or 7 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).
[ solution 98]
The lower limit of the content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-6) is the following compound.
[ solution 99]
(in the formula, RL61And RL62Each independently represents R in the general formula (L)L1And RL2Same meaning as XL61And XL62Each independently represents a hydrogen atom or a fluorine atom. Wherein the compound represented by the general formula (N-1) is excluded. )
RL61And RL62Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. Preferably, the unsaturated bond of the alkenyl group is not directly connected to benzene.
Preferably XL61And XL62One is a fluorine atom and the other is a hydrogen atom.
The compounds represented by the general formula (L-6) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more as one embodiment of the present invention.
The lower limit of the content of the compound represented by the formula (L-6) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention. When the emphasis is placed on increasing Δ n, the content is preferably increased, and when the emphasis is placed on precipitation at a low temperature, the content is preferably decreased.
The compound represented by the general formula (L-6) is preferably a compound represented by the formula (L-6.1) to the formula (L-6.9).
[ solution 100]
The kind of the compound that can be combined is not particularly limited, and these compounds preferably contain 1 to 3 kinds, and more preferably contain 1 to 4 kinds. Further, since the wide molecular weight distribution of the selected compound is effective also for solubility, it is preferable to select 1 from the compounds represented by the formula (L-6.1) or (L-6.2), 1 from the compounds represented by the formula (L-6.4) or (L-6.5), 1 from the compounds represented by the formula (L-6.6) or (L-6.7), 1 from the compounds represented by the formula (L-6.8) or (L-6.9), and appropriately combine them. Among them, preferred are compounds represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9).
The compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formula (L-6.10) to the formula (L-6.17), and among them, a compound represented by the formula (L-6.11) is preferable.
[ solution 101]
The lower limit of the content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of these compounds is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-7) is the following compound.
[ solution 102]
(in the formula, RL71And RL72Each independently represents R in the general formula (L)L1And RL2Same meaning as AL71And AL72Each independently represents a group represented by the general formula (L)L2And AL3Same meaning as AL71And AL72Each hydrogen atom in (A) may independently be substituted by a fluorine atom, ZL71Is represented by Z in the general formula (L)L2Same meaning as XL71And XL72Each independently represents a fluorine atom or a hydrogen atom. Wherein compounds represented by the general formulae (N-1) to (N-3) are excluded. )
In the formula, RL71And RL72Each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. Preferably, the unsaturated bond of the alkenyl group is not directly connected to benzene.
AL71And AL72Each independently of the others preferably being 1, 4-cyclohexylene or 1, 4-phenylene, AL71And AL72Each hydrogen atom may independently be replaced by a fluorine atom,
ZL71preferably a single bond or-COO-, preferably a single bond.
Preferably XL71And XL72Are all hydrogen atoms.
The kind of the compound that can be combined is not particularly limited, and the compound is combined according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2,3, and 4 as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-7) needs to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the formula (L-7) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the above compound is preferably 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When the liquid crystal composition of the present invention is expected to be an embodiment having a high Tni, the content of the compound represented by the formula (L-7) is preferably increased to some extent, and when the liquid crystal composition is expected to be an embodiment having a low viscosity, the content is preferably decreased to some extent.
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), and is preferably a compound represented by the formula (L-7.2).
[ solution 103]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), preferably a compound represented by the formula (L-7.11).
[ solution 104]
The compounds represented by the general formula (L-7) are represented by the formulae (L-7.21) to (L-7.23). Preferred is a compound represented by the formula (L-7.21).
[ solution 105]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), preferably a compound represented by the formula (L-7.31) or/and (L-7.32).
[ solution 106]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), preferably a compound represented by the formula (L-7.41) or/and (L-7.42).
[ solution 107]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.51) to (L-7.53).
[ solution 108]
[4] Others
In the liquid crystal composition of the present invention, the total content of the compound represented by the general formula (II) is preferably 80% by mass or more, 85% by mass or more, 88% by mass or more, 90% by mass or more, 92% by mass or more, 93% by mass or more, 94% by mass or more, 95% by mass or more, 96% by mass, 97% by mass, 98% by mass or more, and 99% by mass or more, based on the total amount of the liquid crystal composition of the present invention. The total content is preferably less than 99.99 mass%, 99.95 mass% or less, 99.5 mass% or less, 99.0 mass% or less, 98 mass% or less, and 95 mass% or less with respect to the total amount of the liquid crystal composition of the present invention.
When the dielectric anisotropy (Δ ∈) of the liquid crystal composition of the present invention at 25 ℃ has a positive value, the total content of the compound selected from the group of compounds represented by the general formulae (M) and (K) and the compound represented by the general formula (L) is preferably 80% by mass or more, 85% by mass or more, 88% by mass or more, 90% by mass or more, 92% by mass or more, 93% by mass or more, 94% by mass or more, 95% by mass or more, 96% by mass or more, 97% by mass or more, 98% by mass or more, and 99% by mass or more, relative to the total amount of the liquid crystal composition of the present invention. The total content is preferably less than 99.99 mass%, 99.95 mass% or less, 99.5 mass% or less, 99.0 mass% or less, 98 mass% or less, and 95 mass% or less with respect to the total amount of the liquid crystal composition of the present invention.
When the dielectric anisotropy (Δ ∈) of the liquid crystal composition of the present invention has a negative value at 25 ℃, the total content of the compound selected from the group of compounds represented by general formulae (N-1) to (N-3) and the compound represented by general formula (L) is preferably 80% by mass or more, 85% by mass or more, 88% by mass or more, 90% by mass or more, 92% by mass or more, 93% by mass or more, 94% by mass or more, 95% by mass or more, 96% by mass or more, 97% by mass or more, 98% by mass or more, and 99% by mass or more, relative to the total amount of the liquid crystal composition of the present invention. The total content is preferably less than 99.99 mass%, 99.95 mass% or less, 99.5 mass% or less, 99.0 mass% or less, 98 mass% or less, and 95 mass% or less with respect to the total amount of the liquid crystal composition of the present invention.
(3) Other additives
In the liquid crystal composition of the present invention, it is preferable that at least one compound selected from 1 or 2 or more antioxidants and ultraviolet absorbers is contained as another additive. This is because the liquid crystal composition of the present invention can improve the reliability of the liquid crystal composition by using at least one compound of an antioxidant and an ultraviolet absorber in combination with the light stabilizer represented by the general formula (H) and utilizing the synergy between the effect of the light stabilizer represented by the general formula (H) and the effect of the antioxidant and the ultraviolet absorber.
The liquid crystal composition of the present invention preferably contains 1 or more antioxidants. By using an antioxidant in addition to the light stabilizer represented by the general formula (H), the impurities generated can be made harmless. The antioxidant may be a known antioxidant used in liquid crystal compositions, and among these, a hindered phenol antioxidant is preferable. This is because the hindered phenol antioxidant has a hindered phenol skeleton and has a structure in which a hydroxyl group is adjacent to an alkyl group having a large steric hindrance, and therefore, the hindered phenol antioxidant is not easily deactivated, and can sufficiently exhibit the function of the antioxidant.
When the liquid crystal composition of the present invention contains an antioxidant, the total content of the antioxidant is preferably 0.0001% by mass or more, preferably 0.005% by mass or more, and preferably 0.01% by mass or more, and on the other hand, the total content is preferably 0.1% by mass or less, preferably 0.05% by mass or less, and preferably 0.03% by mass or less, based on the total amount of the liquid crystal composition of the present invention. If the content of the antioxidant is too large and exceeds the above range, the image quality of a liquid crystal panel may be degraded due to deposition of the antioxidant in a liquid crystal display element using the liquid crystal composition of the present invention, and if it is too small, the reliability of the liquid crystal composition may not be sufficiently improved.
The liquid crystal composition of the present invention preferably contains 1 or more kinds of ultraviolet absorbers. By using the ultraviolet absorber in combination with the light stabilizer represented by the general formula (H), the amount of ultraviolet rays to which the liquid crystal composition is subjected can be reduced, and the photodegradation of the liquid crystal composition can be suppressed. Examples of the ultraviolet absorber include hydroxybenzophenone-based ultraviolet absorbers, hydroxyphenyl benzotriazole-based ultraviolet absorbers, cyanoacrylate-based ultraviolet absorbers, and salicylate-based ultraviolet absorbers. Among them, the liquid crystal composition of the present invention preferably contains 1 or more benzophenone-based ultraviolet absorbers. This is because benzophenone-based ultraviolet absorbers have a smaller number of unpaired electrons in the molecule than other ultraviolet absorbers, and therefore, the purity is easily maintained and the reliability is easily improved. Specific examples of the benzophenone-based ultraviolet absorber include [ 2-hydroxy-4- (octyloxy) phenyl ] (phenyl) methanone (product name: manufactured by ADK STAB 1413 ADEKA). In addition, from the viewpoint of suppressing the decrease in reliability, it is preferable that the ultraviolet absorber not containing a heteroatom other than oxygen.
When the liquid crystal composition of the present invention contains an ultraviolet absorber, the total content of the ultraviolet absorber is preferably 0.0001% by mass or more, preferably 0.001% by mass or more, and preferably 0.01% by mass or more, and on the other hand, the total content is preferably 0.1% by mass or less, preferably 0.05% by mass or less, and preferably 0.02% by mass or less, based on the total amount of the liquid crystal composition of the present invention. If the content of the ultraviolet absorber is too large and exceeds the above range, display defects of the liquid crystal panel due to deposition of the ultraviolet absorber may easily occur in the liquid crystal display element using the liquid crystal composition of the present invention, and if it is too small, the amount of ultraviolet rays received by the liquid crystal molecules may not be reduced, and reliability may not be secured due to deterioration of the liquid crystal molecules.
The liquid crystal composition of the present invention may contain 1 or 2 or more antioxidants, may contain 1 or 2 or more ultraviolet absorbers, and may contain 1 or 2 or more antioxidants and 1 or 2 or more ultraviolet absorbers.
When the liquid crystal composition of the present invention contains a polymerizable compound, the liquid crystal composition of the present invention preferably contains 1 or 2 or more kinds of polymerizable initiators as other additives. This is because, in the production of a liquid crystal display element using the liquid crystal composition of the present invention, polymerization of the polymerizable compound is promoted by using a polymerization initiator in combination with the light stabilizer represented by the general formula (H), and a strong polymer layer (layer formed of a polymer of the polymerizable compound) is formed at the interface between the liquid crystal layer and the substrate, so that the insulating property of the liquid crystal cell is enhanced and VHR can be improved.
The polymerizable initiator may be selected from known polymerizable initiators used in liquid crystal compositions, and examples thereof include benzoin ether type polymerizable initiators, benzophenone type polymerizable initiators, acetophenone type polymerizable initiators, benzil ketal type polymerizable initiators, acylphosphine oxide type polymerizable initiators, and the like. Of these, benzil ketal polymerization initiators are preferred. This is because the benzil ketal polymerization initiator has high photoreaction efficiency and can form a dense polymer layer. Specific examples of the benzil ketal polymerization initiator include 2, 2-dimethoxy-2-phenylacetophenone (product name: Irgacure 651).
When the liquid crystal composition of the present invention contains a polymerization initiator, the total content of the polymerization initiator is preferably 0.0001% by mass or more, and preferably 0.001% by mass or more, based on the total amount of the liquid crystal composition of the present invention. The total content is preferably 0.005 mass% or less and 0.002 mass% or less. If the content of the polymerization initiator is too large and exceeds the above range, VHR may be reduced by the influence of impurities contained in the polymerization initiator, and if it is too small, the polymerizable compound may not be efficiently polymerized, the insulating property of the liquid crystal cell may not be improved, and VHR may not be improved.
When the liquid crystal composition of the present invention contains 1 or 2 or more compounds selected from the group consisting of an antioxidant, an ultraviolet absorber, and a polymerization initiator, the total amount of the compounds selected from the group consisting of an antioxidant, an ultraviolet absorber, and a polymerization initiator is preferably 0.0001% by mass or more, 0.0005% by mass or more, 0.005% by mass or more, 0.01% by mass or more, and 0.2% by mass or less, 0.1% by mass or less, and 0.05% by mass or less, relative to the total amount of the liquid crystal composition of the present invention.
(4) Polymerizable compound
The liquid crystal composition of the present invention may contain 1 or more polymerizable compounds having 1 or more polymerizable groups in 1 molecule. Among these, when the liquid crystal composition of the present invention is used for production of a liquid crystal display device for PSA mode, PSVA mode, PS-IPS mode or PS-FSS mode, the liquid crystal composition of the present invention preferably contains 1 or 2 or more kinds of polymerizable compounds. This is because the polymerizable compound is a compound that can be polymerized by irradiation with active energy rays, and the pretilt angle of the liquid crystal molecules can be appropriately formed.
The polymerizable compound may be a known polymerizable compound used in a liquid crystal composition, and among these, a compound represented by the following general formula (P) is preferable.
[ solution 109]
(in the above general formula (P), Rp1Represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or-Spp2-P p21 or non-adjacent 2 or more-CH groups in the alkyl group2-each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, and 1 or more than 2 hydrogen atoms in the alkyl group may each independently be substituted by cyano groups, fluorine atoms or chlorine atoms,
Pp1and Pp2Each independently represents a general formula (P)p1-1) to formula (P)p1-any one of the above-mentioned-9),
[ solution 110]
(in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or 2, R being in the moleculep11、Rp12、Wp11And/or tp11When a plurality of them exist, they may be the same or different. )
Spp1And Spp2Each independently represents a single bond or a spacer,
Zp1and Zp2Each independently represents a single bond, -O-, -S-, -CH2-、-OCH2-、-CH2O-、-CO-、-C2H4-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CO-NRZP1-、-NRZP1-CO-、-SCH2-、-CH2S-、-CH＝CRZP1-COO-、-CH＝CRZP1-OCO-、-COO-CRZP1＝CH-、-OCO-CRZP1＝CH-、-COO-CRZP1＝CH-COO-、-COO-CRZP1＝CH-OCO-、-OCO-CRZP1＝CH-COO-、-OCO-CRZP1＝CH-OCO-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-(C＝O)-O-(CH2)2-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2-or-C ≡ C- (wherein, R isZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R in the moleculeZP1When a plurality of them exist, they may be the same or different. ),
Ap1、Ap2and Ap3Each independently represents a group selected from the group consisting of,
(ap)1, 4-cyclohexylene (1-CH present in the radical)2-or 2 or more-CH not adjacent2-may be substituted by-O-. )
(bp)1, 4-phenylene (1-CH ═ or nonadjacent 2 or more-CH ═ present in the group can be substituted by-N ═ or. ) And
(cp) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl, phenanthrene-2, 7-diyl, or anthracene-2, 6-diyl (1-CH ═ or 2 or more-CH ═ which are not adjacent and present in these groups may be substituted with-N ═ and hydrogen atoms present in the groups may be substituted with a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 1 to 8 carbon atoms. )
The above group (a)p) Group (b)p) And a group (c)p) Wherein 1 or 2 or more hydrogen atoms present in the group (a) are independently a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms or-Spp2-Pp2Substituted, 1 or non-adjacent 2 or more-CH in the alkyl group2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
mp1represents 0, 1,2 or 3, and Z is in the moleculep1、Ap2、Spp2And/or Pp2When plural, they may be the same or different, in mp1Is 0 and Ap1When it is phenanthrene-2, 7-diyl or anthracene-2, 6-diyl Ap3Represents a single bond. )
Wherein the compound represented by the general formula (I) is excluded. )
The liquid crystal composition of the present invention preferably contains 1 or 2 or more kinds of polymerizable compounds represented by the general formula (P).
In the general formula (P), Rp1Is preferably-Spp2-Pp2。
In the general formula (P), Pp1And Pp2Are each independently preferably of the formula (P)p1-1) to formula (P)p1-3), preferably (P)p1-1)。
In the general formula (P), Rp11And Rp12Each independently preferably a hydrogen atom or a methyl group.
In the general formula (P), tp11Preferably 0 or 1.
In the general formula (P), Wp11Preferably a single bond, methylene or ethylene.
In the general formula (P), mp1Preferably 0, 1 or 2, preferably 0 or 1.
In the general formula (P), Zp1And Zp2Each independently preferably being a single bond, -OCH2-、-CH2O-、-CO-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-CF2-、-CF2O-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2-、-OCF2-or-C ≡ C-, preferably a single bond, -OCH2-、-CH2O-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2-or-C.ident.C-, preferably only 1 present in the molecule is-OCH2-、-CH2O-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2-or-C.ident.C-and all others are single bonds, preferably only 1 present in the molecule is-OCH2-、-CH2O-、-C2H4-, -COO-or-OCO-and the others are all single bonds, preferably all single bonds.
In addition, Z present in the molecule is preferablep1And Zp2Is selected from the group consisting of-CH-COO-, -COO-CH-, - (CH)2)2-COO-、-(CH2)2-OCO-、-O-CO-(CH2)2-、-COO-(CH2)2-a linker group of the group and others are single bonds.
In the general formula (P), Spp1And Spp2Each independently represents a single bond or a spacer, the spacer is preferably an alkylene group having 1 to 30 carbon atoms, the-CH group in the alkylene group2The alkylene group may be substituted with-O-, -CO-, -COO-, -OCO-, -CH-or-C.ident.C-so that oxygen atoms are not directly bonded to each other, and a hydrogen atom in the alkylene group may be substituted with a halogen atom, and is preferably a linear alkylene group having 1 to 10 carbon atoms or a single bond.
In the general formula (P), Ap1、Ap2And Ap3Independently of one another, 1, 4-phenylene or 1, 4-cyclohexylene is preferred, 1, 4-phenylene being preferred. In order to improve the compatibility with the liquid crystal compound, the 1, 4-phenylene group is preferably substituted with 1 fluorine atom, 1 methyl group or 1 methoxy group.
The lower limit of the total content of the compounds represented by the general formula (P) is preferably 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, 0.3 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the total content of the compounds represented by the general formula (P) is preferably 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, 0.5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The preferable range of the total content of the compounds represented by the general formula (P) may be set by combining the upper limit value and the lower limit value. The total content is preferably 0.05 to 10% by mass, more preferably 0.1 to 8% by mass, even more preferably 0.1 to 5% by mass, even more preferably 0.1 to 3% by mass, even more preferably 0.2 to 2% by mass, even more preferably 0.2 to 1.3% by mass, particularly preferably 0.2 to 1% by mass, and most preferably 0.2 to 0.56% by mass, based on the total amount of the liquid crystal composition of the present invention.
When the content of the compound represented by the general formula (P) is small, the effect of the polymerizable compound is hardly exhibited, and the problem of weak orientation-restraining force of the liquid crystal composition or weakening with time occurs. On the other hand, if the content of the compound represented by the general formula (P) is too large, there arise problems such as an increase in the amount of unreacted polymerizable compound remaining after curing, a long time required for curing, and a decrease in reliability of liquid crystal.
Examples of the compounds represented by the general formula (P) include compounds represented by the following general formulae (P-1-1) to (P-1-46).
[ solution 111]
[ solution 112]
[ solution 113]
[ chemical formula 114]
[ solution 115]
(in the formula, Pp11、Pp12、Spp11And Spp12Represents P in the general formula (P)p1、Pp2、Spp1And Spp2The same meaning is used. )
Preferred examples of the compound represented by the general formula (P) include compounds represented by the following general formulae (P-2-1) to (P-2-14).
[ solution 116]
[ solution 117]
(in the formula, Pp21、Pp22、Spp21And Spp22Represents P in the general formula (P)p1、Pp2、Spp1And Spp2The same meaning is used. )
Preferred examples of the compound represented by the general formula (P) include compounds represented by the following general formulae (P-3-1) to (P-3-15).
[ chemical formula 118]
[ solution 119]
(in the formula, Pp31、Pp32、Spp31And Spp32Represents P in the general formula (P)p1、Pp2、Spp1And Spp2The same meaning is used. )
Preferred examples of the compound represented by the general formula (P) include compounds represented by the following general formulae (P-4-1) to (P-4-21).
[ chemical formula 120]
[ solution 121]
[ chemical formula 122]
[ solution 123]
(in the formula, Pp41、Pp42、Spp41And Spp42Represents P in the general formula (P)p1、Pp2、Spp1And Spp2The same meaning is used. )
(5) Other Compounds
The liquid crystal composition of the present invention may further contain a conventional nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, infrared absorber, and the like.
The liquid crystal composition of the present invention may or may not contain a self-aligning compound. The spontaneous alignment compound is a compound that can achieve vertical alignment of liquid crystal molecules even without an alignment film, and is represented by, for example, the following formula (Q).
[ solution 124]
MES-R2 (Q)
(in the formula (Q), MES is mesogenic group, which contains each directly or indirectly connected with more than 1 ring, and directly or via a spacer connected to MES as arbitrary components of more than 1 polymeric group,
R2are polar anchoring groups preferably comprising at least 1 OH or primary or secondary amine functional group. )
(6) Others
The liquid crystal composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are linked to each other, such as a peracid (-CO-OO-) structure in the molecule.
When importance is attached to the reliability and long-term stability of the liquid crystal composition, the content of the compound having a carbonyl group is preferably 5% by mass or less, more preferably 3% by mass or less, further preferably 1% by mass or less, and most preferably substantially none, based on the total amount of the liquid crystal composition.
When importance is attached to the stability of the liquid crystal composition by UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% by mass or less, preferably 10% by mass or less, preferably 8% by mass or less, more preferably 5% by mass or less, preferably 3% by mass or less, and further preferably substantially not contained, relative to the total amount of the liquid crystal composition of the present invention.
In the liquid crystal composition of the present invention, the content of the compound having all ring structures in the molecule as 6-membered rings is preferably large. The content of the compound having 6-membered ring structures in all the ring structures in the molecule is preferably 80% by mass or more, more preferably 90% by mass or more, further preferably 95% by mass or more, based on the total amount of the liquid crystal composition of the present invention, and the liquid crystal composition of the present invention is most preferably constituted by substantially only the compound having 6-membered ring structures in all the ring structures in the molecule.
In order to suppress deterioration due to oxidation of the liquid crystal composition, the content of the compound having a cyclohexenylene group as a ring structure in the liquid crystal composition of the present invention is preferably small. The content of the compound having a cyclohexenylene group is preferably 10% by mass or less, preferably 8% by mass or less, more preferably 5% by mass or less, preferably 3% by mass or less, and further preferably substantially none, relative to the total amount of the liquid crystal composition of the present invention.
When importance is attached to the improvement of viscosity and the improvement of Tni, the content of the compound having 2-methylbenzene-1, 4-diyl in which a hydrogen atom in a molecule may be substituted with halogen is preferably small in the liquid crystal composition of the present invention. The content of the compound having 2-methylbenzene-1, 4-diyl in the molecule is preferably 10% by mass or less, preferably 8% by mass or less, more preferably 5% by mass or less, preferably 3% by mass or less, and further preferably substantially none, relative to the total amount of the liquid crystal composition of the present invention.
The term "substantially free" in the present specification means that the compound is not contained except for substances (inevitable impurities) which are not intentionally contained.
When the liquid crystal composition of the present invention has a positive dielectric anisotropy (. DELTA.. di-elect cons.), the dielectric anisotropy (. DELTA.. di-elect cons.) at 25 ℃ of the liquid crystal composition of the present invention is preferably in the range of 1.5 to 20.0, more preferably in the range of 1.5 to 18.0, more preferably in the range of 1.5 to 15.0, further preferably in the range of 1.5 to 11, and particularly preferably in the range of 1.5 to 8.
Further, when the liquid crystal composition of the present invention has a negative dielectric anisotropy (. DELTA.. di-elect cons.), the dielectric anisotropy (. DELTA.. di-elect cons.) at 25 ℃ of the liquid crystal composition of the present invention is preferably-2 or less, more specifically preferably-2.0 to-8.0, more preferably-2.0 to-6.0, still more preferably-2.0 to-5.0, and particularly preferably-2.5 to-4.0.
The refractive index anisotropy (. DELTA.n) at 25 ℃ of the liquid crystal composition of the present invention is preferably in the range of 0.08 to 0.14, more preferably in the range of 0.09 to 0.13, and particularly preferably in the range of 0.09 to 0.12. In further detail, it is preferably in the range of 0.10 to 0.13 in correspondence with a thin cell gap, and in the range of 0.08 to 0.10 in correspondence with a thick cell gap.
The viscosity (. eta.) at 25 ℃ of the liquid crystal composition of the present invention is 10 to 50 mPas, more preferably 10 to 40 mPas, and particularly preferably 10 to 35 mPas.
Rotational viscosity at 25 ℃ of the liquid Crystal composition of the present invention (. gamma.)1) Preferably in the range of from 40 to 130 mPas, more preferably in the range of from 50 to 110 mPas, particularly preferably in the range of from 60 to 100 mPas.
Nematic phase-isotropic liquid phase transition temperature (T) of liquid crystal composition of the present inventionni) Preferably in the range of 60 ℃ to 120 ℃, more preferably in the range of 70 ℃ to 100 ℃, and particularly preferably in the range of 70 ℃ to 85 ℃.
The liquid crystal composition of the present invention can be suitably used for liquid crystal display elements, and among these, can be suitably used for liquid crystal display elements for active matrix driving, and can be suitably used for liquid crystal display elements of PSA type, PSVA type, VA type, IPS type, FFS type, TN type, or ECB type. The liquid crystal composition of the present invention can be suitably used for a liquid crystal display element in which a liquid crystal layer is interposed between a pair of opposing alignment films, and particularly, when the liquid crystal composition of the present invention contains a polymerizable compound, can be suitably used for PSA mode, PSVA mode, PS-IPS mode, or PS-FSS mode applications. Further, when the polymerizable liquid crystal composition of the present invention contains a self-aligning compound, it can also be used for a liquid crystal display element not having an alignment film.
Liquid crystal display element
The liquid crystal display element of the present invention is a liquid crystal display element using the liquid crystal composition described in the above "i. The liquid crystal display element of the present invention can have excellent display quality without causing or suppressing display failure by using the liquid crystal composition.
The liquid crystal display element of the present invention may be an active matrix driving liquid crystal display element. The liquid crystal display element of the present invention may be a PSA type, PSVA type, VA type, IPS type, FFS type, TN type, or ECB type liquid crystal display element, and is preferably a PSA type or PSVA type liquid crystal display element.
Fig. 1 is a schematic diagram showing an example of a liquid crystal display element of the present invention. The structure of the liquid crystal display element of the present invention is not limited to this example. In fig. 1, the respective components are shown separately for convenience of explanation. The liquid crystal display element 1 shown in fig. 1 includes a first substrate 2 and a second substrate 3 which are disposed to face each other, and a liquid crystal layer 4 provided between the first substrate 2 and the second substrate 3.
As illustrated in fig. 1, a pixel electrode layer 5 is formed on the first substrate 2 on the liquid crystal layer 4 side. A common electrode layer 6 is formed on the second substrate 3 on the liquid crystal layer 4 side. The first substrate 2 and the second substrate 3 may be sandwiched by a pair of polarizing plates 7, 8. On the liquid crystal layer 4 side of the second substrate 3, a color filter 9 may be further provided.
The liquid crystal layer 4 includes the liquid crystal composition described in the above "i. In the case of a liquid crystal display element manufactured using a liquid crystal composition containing a polymerizable compound, it is considered that the polymer of the polymerizable compound generated by ultraviolet irradiation during the manufacturing process is unevenly distributed on the first substrate 2 and the second substrate side in the liquid crystal layer 4. That is, in the above case, it is considered that a polymer layer made of a polymer of a polymerizable compound is formed at the interface between the liquid crystal layer 4 and the first substrate 2 and the second substrate.
Although not shown in the drawings, the liquid crystal display device of the present invention generally includes a first substrate and a second substrate facing each other, and a liquid crystal layer containing the liquid crystal composition and provided between the first substrate and the second substrate, wherein the first substrate has a first alignment film on a surface on the liquid crystal layer side, and the second substrate has a second alignment film on a surface on the liquid crystal layer side. That is, the liquid crystal display element of the present invention may be configured such that a first polarizing plate, a first substrate, a first alignment film, a pixel electrode layer, a liquid crystal layer, a common electrode layer, a color filter, a second alignment film, a second substrate, and a second polarizing plate are sequentially stacked. As the alignment film, an alignment film commonly used in liquid crystal display devices such as a polyimide alignment film can be used.
In addition. In the liquid crystal display device of the present invention, the alignment film may not be provided on one or both of the first substrate and the second substrate. In this case, the liquid crystal display element of the present invention is manufactured using a liquid crystal composition containing a self-aligning compound, and forms a self-aligning compound layer composed of a polymer of the self-aligning compound at an interface of a liquid crystal layer, thereby aligning the liquid crystal compound without an alignment film.
The method for producing the liquid crystal display element of the present invention is not particularly limited as long as the liquid crystal composition described in the above "i.
The present invention is not limited to the above embodiments. The above-described embodiments are merely illustrative, and it is needless to say that embodiments having substantially the same configuration as the technical idea described in the claims of the present invention and exhibiting the same operational effects are also included in the technical scope of the present invention.
Examples
The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the examples.
The compounds in examples and comparative examples are described by the following abbreviations.
(side chain)
-n -CnH2n+1Straight-chain alkyl group having n carbon atoms
n- CnH2n+1-a linear alkyl group having n carbon atoms
-On -OCnH2n+1Straight-chain alkoxy group having n carbon atoms
nO- CnH2n+1O-straight-chain alkoxy group having n carbon atoms
-V -CH＝CH2
V- CH2＝CH-
-V1 -CH＝CH-CH3
1V- CH3-CH＝CH-
-2V -CH2-CH2-CH＝CH2
V2- CH2＝CH-CH2-CH2-
-2V1 -CH2-CH2-CH＝CH-CH3
1V2- CH3-CH＝CH-CH2-CH2-
OCF3 -O-CF3
Fluorine atoms of-F-F
F- -F fluorine atom
(linker)
-CFFO- -CF2-O-
-OCFF- -O-CF2-
-1O- -CH2-O-
-O1- -O-CH2-
-COO- -COO-
-OCO- -OCO-
(Ring structure)
< light stabilizer represented by the general formula (H) >
As the light stabilizer (polymerizable acetal light stabilizer) represented by the general formula (H), the following compounds were used.
[ solution 125]
[ solution 126]
< ultraviolet absorber >
As the ultraviolet absorber, the following compounds were used.
[ solution 127]
< antioxidant >
As the antioxidant, the following compounds were used.
[ solution 128]
< light stabilizers other than the light stabilizers represented by the general formula (H) >
As the light stabilizer other than the light stabilizer represented by the general formula (H), the following compounds (generally referred to as compounds of formula (R)) are used. The compounds represented by the formulae (R-1) and (R-2) are non-polymerizable non-acetal light stabilizers having no polymerizable group and no acetal skeleton, respectively. The compound represented by the formula (R-3) is a polymerizable non-acetal light stabilizer having a polymerizable group but no acetal skeleton.
[ solution 129]
< polymerizable Compound >
As the polymerizable compound, the following compounds were used.
[ solution 130]
The characteristics obtained by measuring the liquid crystal composition examples used in the examples and comparative examples are as follows.
Tni: nematic phase-isotropic liquid phase transition temperature (. degree.C.)
Δ n: refractive index anisotropy at 25 DEG C
Δ ε: anisotropy of dielectric constant at 25 DEG C
γ1：2Rotational tack at 5 ℃ (mPa. multidot.s)
[ Voltage holding ratio ]
The liquid crystal cells obtained in examples and comparative examples were irradiated with Ultraviolet (UV) light for 90 minutes at an intensity of 313nm of 0.3mW using a fluorescent lamp, and then measured for a Voltage Holding Ratio (VHR) under conditions of 1V, 0.6Hz, and 60 ℃.
[ solubility (Low-temperature storage Property) ]
The liquid crystal compositions obtained in examples and comparative examples were stored in a freezer at-35 ℃ for 1000 hours. It was confirmed whether or not precipitation occurred in the liquid crystal composition after storage.
Good: no precipitation at-35 deg.C
And (delta): little precipitation at-35 DEG C
X: precipitation at-35 deg.C
-: non-evaluation object
(preparation of mother compositions LC-A to LC-D)
The precursor compositions LC-A to LC-D were prepared, and their physical property values were measured. Table 1 shows the constituent compounds of each base composition, their amounts (mass%) added, and the physical property values of each base composition.
[ Table 1]
| LC-A | LC-B | LC-C | LC-D | |
| 3-Ph-Ph-1 | 8 | 9 | ||
| 3-Cy-Cy-V | 29 | |||
| 3-Cy-Cy-2 | 5 | 23 | 21 | 21 |
| 3-Cy-Cy-4 | 10 | 8 | 9 | |
| 3-Cy-Cy-5 | 5 | |||
| 3-Cy-Ph-01 | 7 | |||
| 3-Cy-Ph-Ph-1 | 6 | |||
| 3-Cy-Ph-Ph-2 | 6 | 4 | ||
| 5-Cy-Ph-Ph-2 | 7 | 4 | ||
| 3-Cy-Ph5-02 | 13 | 15 | 15 | |
| 5-Cy-Ph5-02 | 13 | |||
| 3-Cy-10-Ph5-01 | 8 | |||
| 3-Cy-10-Ph5-02 | 8 | |||
| 2-Ph-Ph5-02 | 9 | 7 | 7 | |
| 3-Ph-Ph5-02 | 9 | 8 | 7 | |
| 3-Ph-Ph5-03 | 7 | 7 | ||
| 3-Ph-Ph5-04 | 7 | 7 | ||
| 3-Cy-Cy-10-Ph5-02 | 14 | |||
| 3-Cy-Cy-10-Ph5-04 | 12 | |||
| 2-Cy-Cy-Ph5-02 | 9 | |||
| 3-Cy-Cy-Ph5-02 | 5 | |||
| 3-Ph-Ph5-Ph-1 | 7 | |||
| 3-Ph-Ph5-Ph-2 | 8 | |||
| 3-Cy-Ph-Ph5-02 | 8 | |||
| 3-Cy-Ph-Ph5-04 | 8 | |||
| Total [ wt.%] | 100 | 100 | 85 | 100 |
| Tni[℃] | 76 | 73.1 | 74.8 | 75 |
| Δn | 0.109 | 0.11 | 0.112 | 0.105 |
| r1[mPa·s] | 95 | 99 | 92 | 102 |
| Δε | -3.6 | -2.5 | -2.0 | -2.8 |
(example 1)
A100 mass% liquid crystal composition LC-1 was prepared by mixing 99.65 mass% of the base composition LC-A, 0.05 mass% of the compound of formula (H-1) and 0.3 mass% of the compound of formula (M-1). The liquid crystal composition LC-1 is a liquid crystal composition having a negative dielectric anisotropy (. DELTA.. di-elect cons.), TniΔ n, Δ ε and γ1Value of andthe values for the parent composition LC-a were the same. Then, the liquid crystal composition LC-1 was vacuum-injected into a cell having a gap of 3.5 μm of a vertical alignment film (JALS2096) on a transparent electrode, and then a blocking material (3026B) was applied to the injection port, followed by irradiation with ultraviolet rays of 380nm for 10 seconds to block the cell, thereby obtaining a liquid crystal cell.
(examples 2 to 11)
Liquid crystal compositions LC-2 to LC-11 were prepared in the same manner as in example 1 at the respective formulation ratios shown in table 2. In table 2, each value in parentheses represents the amount (mass%) of the compound, and the same is true in table 3 and the following tables. Liquid crystal compositions LC-2 to LC-11 are respectively a liquid crystal composition having negative dielectric anisotropy (Delta epsilon), and T of liquid crystal compositions LC-2 to LC-11niΔ n, Δ ε and γ1Respectively, are the same as the values of the parent composition LC-a. Next, liquid crystal cells were produced in the same manner as in example 1 using each of the liquid crystal compositions LC-2 to LC-11.
The solubility of the liquid crystal compositions obtained in examples 1 to 11 and the VHR of each liquid crystal cell are shown in Table 2.
[ Table 2]
Comparative examples 1 to 5
Liquid crystal compositions LC-20 to LC-24 were prepared in the proportions shown in Table 3. The liquid crystal compositions LC-20 to LC-24 are liquid crystal compositions having negative dielectric anisotropy (. DELTA.. di-elect cons.), respectively. Next, liquid crystal cells were produced in the same manner as in example 1 using the liquid crystal compositions LC-20 to LC-24, respectively.
The solubility of the liquid crystal compositions obtained in comparative examples 1 to 5 and the VHR of the liquid crystal cells are shown in Table 3.
[ Table 3]
From the results of tables 2 and 3, the liquid crystal cell of example 1 and the liquid crystal cells of comparative examples 1 to 3 exhibited a high VHR as compared with the liquid crystal cells of comparative examples 4 to 5. The liquid crystal cells of example 1 and the liquid crystal cells of comparative examples 1 to 3 differ from each other in that a liquid crystal composition containing a light stabilizer is used, whereas the liquid crystal cells of comparative examples 4 to 5 are different from each other in that a liquid crystal composition containing no light stabilizer is used. From the above results, it was revealed that the inclusion of the light stabilizer suppressed the deterioration of the liquid crystal composition and increased the VHR as compared with the case where the light stabilizer was not included.
The liquid crystal cells of example 1 and comparative example 3 exhibited a higher VHR than the liquid crystal cells of comparative examples 1 to 2. The liquid crystal cells of examples 1 and comparative examples 3 differ from each other in that a liquid crystal composition containing a polymerizable light stabilizer having a polymerizable group is used, whereas the liquid crystal cells of comparative examples 1 to 2 are different from each other in that a liquid crystal composition containing a non-polymerizable light stabilizer having no polymerizable group is used. From the above results, it was found that by providing a light stabilizer with a polymerizable group, deterioration of the liquid crystal composition was further suppressed and VHR was further increased as compared with the case where no polymerizable group was provided.
Further, the liquid crystal cell of example 1 exhibited a higher VHR than the liquid crystal cell of comparative example 3. The liquid crystal cell of example 1 differs from the liquid crystal cell of comparative example 3 in that a liquid crystal composition containing a polymerizable light stabilizer having a polymerizable group and an acetal skeleton is used. From the above results, it was revealed that by using a light stabilizer having an acetal skeleton and a polymerizable group (i.e., the compound represented by formula (H)), the deterioration of the liquid crystal compound was suppressed and VHR became higher than the case of using a polymerizable light stabilizer having a non-acetal skeleton.
As is clear from the comparison of the liquid crystal cells of examples 6 to 11 with the liquid crystal cells of comparative examples 1 to 6, the same effects as in example 1 were exhibited even when a liquid crystal composition containing the compounds of formulae (H-1) to (H-7) in place of the compound of formula (H-1) was used.
As is clear from examples 4 to 5, the effects obtained by including the compound represented by the formula (H) are exhibited regardless of the type of polymerizable compound or the like.
(examples 12 to 14, comparative examples 6 to 8)
Liquid crystal compositions LC-12 to LC-14 and LC-25 to LC-27 were prepared in the proportions shown in Table 4, respectively. Liquid crystal compositions LC-12 to LC-14 and LC-25 to LC-27 are respectively a liquid crystal composition having negative dielectric anisotropy (. DELTA.. di-elect cons.), and T of liquid crystal compositions LC-12 and LC-25niΔ n, Δ ε and γ1Respectively, of the liquid crystal compositions LC-13 and LC-26niΔ n, Δ ε and γ1Respectively, of the liquid crystal compositions LC-14 and LC-27niΔ n, Δ ε and γ1The values of (a) are respectively the same as the values of the parent composition LC-D. Liquid crystal cells were then produced in the same manner as in example 1, using liquid crystal compositions LC-12 to LC-14 and LC-25 to LC-27, respectively.
The solubilities of the liquid crystal compositions obtained in examples 12 to 14 and comparative examples 6 to 8 and VHR of the liquid crystal cells are shown in Table 4.
[ Table 4]
From the results in Table 4, even when the mother compositions were different, the liquid crystal cell using the liquid crystal composition containing the compound of formula (H-1) exhibited a VHR higher than that of the liquid crystal cell using the liquid crystal composition containing the compound of formula (R-1) having no polymerizable group and acetal skeleton.
(examples 15 to 19)
Liquid crystal compositions LC-15 to LC-19 were prepared in the proportions shown in Table 5. Liquid crystal compositions LC-15 to LC-19 are respectively a liquid crystal composition having negative dielectric anisotropy (Delta epsilon), and T of liquid crystal compositions LC-15 to LC-19niΔ n, Δ ε and γ1Respectively, are the same as the values of the parent composition LC-a. Next, the same procedures as in example 1 were repeated using liquid crystal compositions LC-15 to LC-19, respectivelyThe method of (3) fabricating a liquid crystal cell.
The solubility of the liquid crystal compositions obtained in examples 15 to 19 and the VHR of each liquid crystal cell are shown in Table 5.
[ Table 5]
As taught in table 5, the liquid crystal cell using the liquid crystal composition in which the compound of formula (H) is used in combination with a light stabilizer, an antioxidant and an ultraviolet absorber other than the compound of formula (H) exhibits a high VHR in the same manner, and the reduction in VHR due to the addition of other additives is suppressed.
In addition, as shown in tables 2 to 5, the liquid crystal compositions of examples 1 to 19 were good in solubility as compared with the liquid crystal compositions of comparative examples 1 to 8. The results show that the liquid crystal composition of the present invention has good solubility, can achieve high VHR, can sufficiently suppress precipitation of the compound of formula (H), and has excellent storage stability. In particular, it teaches that: by setting the amount of the compound of formula (H) to 0.1% by mass or less based on 100% by mass of the liquid crystal composition, the solubility (storage stability) is further improved. The liquid crystal composition of example 14 contains 2 compounds of formula (H), and the solubility is as good as in example 1, although the total content of the compounds of formula (H) is increased as compared with example 1 containing only 1 compound of formula (H).
In the liquid crystal compositions of examples 1 to 19 and comparative examples 1 to 8, even when the polymerizable compound was not contained, the VHR after UV irradiation was improved as compared with the liquid crystal composition containing a light stabilizer other than the compound of the formula (H). In addition, in the liquid crystal display devices using the liquid crystal compositions obtained in examples 1 to 19, it was confirmed that no display failure was observed, and the response was sufficiently high-speed.
(preparation of mother composition LC-E)
The base composition E was prepared, and the physical property values thereof were measured. Table 6 shows the constituent compounds of the base composition E, their amounts (% by mass) incorporated, and physical property values.
[ Table 6]
| LC-E | |
| 3-Cy-Cy-V | 48 |
| 3-Cy-Cy-Ph-1 | 15 |
| 2-Ph-Ph1-Ph-2V | 2 |
| 3-Ph-Ph5-CF20-Ph2- |
8 |
| 3-Cy-Ph-Ph1-Ph5-OCF3 | 4.5 |
| 3-Ph-Ph1-Ph2-CF20-Ph2-F | 4 |
| 4-Ph-Ph1-Ph2-CF20-Ph2-F | 7 |
| 2-Py-Ph-Ph2-CF20-Ph2-F | 5 |
| 3-Py-Ph-Ph2-CF20-Ph2-F | 5 |
| 4-0c-Ph-Ph1-Ph2-F | 1.5 |
| Total [ wt.%] | 100 |
| TN1/℃ | 80.9 |
| Δn | 0.1123 |
| Δε | 10.76 |
| γ1[mPa·s] | 87 |
(example 20 and comparative example 9)
Liquid crystal compositions LC-28 and LC-29 were prepared in the proportions shown in Table 7. Liquid crystal compositions LC-28 and LC-29 are respectively a liquid crystal composition having a positive dielectric anisotropy (. DELTA.. di-elect cons.), and T of liquid crystal compositions LC-28 and LC-29niΔ n, Δ ε and γ1Respectively, are the same as the values of the parent composition LC-E. Then, liquid crystal cells were produced in the same manner as in example 1 using liquid crystal compositions LC-28 and LC-29, respectively. VHR and solubility of each liquid crystal cell obtained in example 20 and comparative example 9 are shown in table 7.
[ Table 7]
As shown in table 7, the liquid crystal cell of example 20 exhibited a higher VHR than the liquid crystal cell of comparative example 9. From the above results, it was found that a liquid crystal composition containing a light stabilizer having an acetal skeleton and a polymerizable group (i.e., the compound represented by formula (H)) inhibited deterioration of the liquid crystal compound and increased VHR, and had excellent solubility and storage stability, compared to a liquid crystal composition containing a conventional light stabilizer, regardless of whether Δ ∈ of the liquid crystal composition was positive or negative. In addition, it was confirmed that the liquid crystal display element using the liquid crystal composition obtained in example 20 did not have display defects and sufficiently achieved high-speed response.
Claims (15)
1. A liquid crystal composition comprising 1 or 2 or more light stabilizers represented by the general formula (H),
[ solution 1]
In the general formula (H), Ra0Represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 3 to 12 carbon atoms,
Ra1、Ra2、Ra3and Ra4Each independently represents an alkyl group having 1 to 6 carbon atoms, or Ra1And Ra2And/or Ra3And Ra4May be formed together in a ring structure,
Ra5and Ra6Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Ra0、Ra1、Ra2、Ra3、Ra4、Ra5and Ra6When a plurality of the compounds are present, they may be the same or different,
n represents a number of 0 or 1,
t represents a number of 1 to 4,
u represents a 2 x t-valent organic group forming a ring structure,
and U has 1 or more polymerizable groups P in the groupH。
2. The liquid crystal composition according to claim 1, wherein t represents 1, and U is a structure represented by the following general formula (U-1),
[ solution 2]
In the general formula (U-1), the dotted lines each represent a bond to an oxygen atom,
Ra7and Ra8Each independently represents a hydrogen atom or a 1-valent organic group, or Ra7And Ra8May be formed together in a ring structure,
m represents a number of 0 or 1,
at least Ra8Having 1 or more of the polymerizable group PH。
3. The liquid crystal composition according to claim 2, wherein in the general formula (U-1), R isa7Represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or-SpH-PHIs said SpHRepresents a spacer group, and is represented by,
the R isa8Is a structure represented by the following general formula (r),
[ solution 3]
In the general formula (r), Spa1Represents a single bond, -O-, -CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH＝CH-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-OOCO-、-OCH2CH2O-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-CH＝C(CH3)COO-、-OCOC(CH3)＝CH-、-CH2-CH(CH3)COO-、-OCOCH(CH3)-CH2Or a linear or branched alkylene group having 1 to 10 carbon atoms, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2May be substituted by-O-, -COO-or-OCO-,
Spa2represents a single bond,-O-、-CO-、-CH＝CH-、-CF＝CF-、-C≡C-、-COO-、-OCO-、-OCOO-、-OOCO-、-CF2O-、-OCF2-、-CH＝CHCOO-、-OCOCH＝CH-、-CH＝C(CH3)COO-、-OCOC(CH3)＝CH-、-CH2-CH(CH3)COO-、-OCOCH(CH3)-CH2-、-OCH2CH2O-, or a C1-10 linear or branched alkylene group, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2May be substituted by-O-, -COO-or-OCO-,
Aa1and Aa2Each independently represents a group selected from the group consisting of a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring and a 2-valent condensed polycyclic ring, and 1 or more hydrogen atoms in the ring structure of these groups may be replaced by Li1The substitution is carried out by the following steps,
Li1represents a halogen atom, a cyano group, a nitro group or-SpH-PH1-valent organic radical Ki1A C1-30 linear or branched alkyl group or a C1-30 linear or branched haloalkyl group, or-CH in the alkyl group or haloalkyl group2-may be substituted with-CH ═ CH-, -C.ident.C-, -O-, -NH-, -COO-, -OCO-or-OCOO-but-O-is not continuous,
the 1-valent organic group Ki1Represents a group represented by the following general formula (K1),
[ solution 4]
In the formula, Rk0To Rk6And nkAre respectively R in the general formula (H)a0To Ra6And n is as defined for Rk7And mkAre respectively R in the general formula (U-1)a7And m is the same as defined above, represents a bond,
Ra9represents a hydrogen atom, -SpH-PHA C1-30 linear or branched alkyl group or a C1-30 linear or branched haloalkyl group, the alkyl groupOr 1-CH in haloalkyl2-or 2 or more-CH not adjacent2-may be substituted but-oxo-discontinuous by-CH ═ CH-, -C.ident.C-, -O-, -S-, -NH-, -CO-, -COO-, -OCO-or-OCOO-,
p and q each represents an integer of 0, 1,2 or 3,
when p represents 2 or 3, a plurality of Spa1May be the same or different, and a plurality of the above-mentioned A's may be presenta1Which may be the same or different from each other,
when q represents 2 or 3, a plurality of Spa2May be the same or different, and a plurality of the above-mentioned A's may be presenta2Which may be the same or different from each other,
PHrepresents a polymerizable group, SpHRepresents a spacer group, and is represented by,
wherein the general formula (r) has more than 1-SpH-PHIn the formula,. indicates a bond.
4. The liquid crystal composition according to any one of claims 1 to 3, 1 or more of the polymerizable groups PHEach independently is a group selected from the group represented by the formulae (P-1) to (P-17),
[ solution 5]
In the formula, black dots represent connecting bonds.
5. The liquid crystal composition according to any one of claims 1 to 4, further comprising 1 or 2 or more compounds represented by the general formula (II),
[ solution 6]
In the general formula (II), RII1Represents an alkyl group having 1 to 10 carbon atoms, 1 or non-adjacent 2 or more-CH groups in the alkyl group2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
AII1and AII2Each independently represents a group selected from the group consisting of,
(a)1, 4-cyclohexylene radical, 1-CH present in this radical2-or 2 or more-CH not adjacent2-may be substituted by-O-;
(b)1, 4-phenylene, 1-CH ═ or nonadjacent 2 or more-CH ═ present in the group can be substituted by-N ═ or; and
(c) 1-CH or not adjacent 2 or more-CH present in naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ in the molecule,
the group (a), the group (b) and the group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
ZII1represents a single bond, -CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
YII1represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, 1 or non-adjacent 2 or more-CH groups in the alkyl group2-each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, and 1 or 2 or more hydrogen atoms in the alkyl group may be substituted by fluorine atoms,
mII1represents 1,2,3 or 4, when mII1When 2,3 or 4 is represented, a plurality of AII1And a plurality of ZII1Each may be the same or different.
6. The liquid crystal composition according to claim 5, comprising 1 or 2 or more of at least 1 of said Z in said general formula (II)II1represents-CH2A compound of O-.
7. The liquid crystal composition according to claim 5 or 6, comprising 1 or 2 or more compounds represented by the general formula (L-1A),
[ solution 7]
In the general formula (L-1A), RL11AAnd RL12AEach independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent 2 or more-CH2-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-, RL11AAnd RL12A1 or non-adjacent 2 or more-CH in the alkyl group2Each independently may be substituted by-CH ═ CH-.
8. The liquid crystal composition according to any one of claims 1 to 7, having a negative value of dielectric anisotropy Δ ∈ at 25 ℃.
9. The liquid crystal composition according to any one of claims 1 to 7, having a positive value for dielectric anisotropy Δ ε at 25 ℃.
10. The liquid crystal composition according to any one of claims 1 to 9, wherein the total amount of the content of the general formula (H) is 0.01% by mass or more and 5% by mass or less with respect to the total amount of the liquid crystal composition.
11. The liquid crystal composition according to any one of claims 1 to 10, having a refractive index anisotropy Δ n at 25 ℃ in the range of 0.08 to 0.14, a rotational viscosity γ 1 at 25 ℃ in the range of 60 to 130 mPa-s, and a nematic phase-isotropic liquid phase transition temperature Tni in the range of 60 to 120 ℃.
12. The liquid crystal composition according to any one of claims 1 to 11, comprising 1 or 2 or more kinds of polymerizable compounds.
13. The liquid crystal composition according to any one of claims 1 to 12, comprising 1 or 2 or more compounds of at least one of an antioxidant and an ultraviolet absorber.
14. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 13.
15. The liquid crystal display element according to claim 14, comprising a first substrate and a second substrate facing each other, and a liquid crystal layer provided between the first substrate and the second substrate and containing the liquid crystal composition, wherein the first substrate has a first alignment film on a surface on the liquid crystal layer side, and the second substrate has a second alignment film on a surface on the liquid crystal layer side.
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