WO2018235713A1

WO2018235713A1 - Liquid crystal composition and liquid crystal display element using same

Info

Publication number: WO2018235713A1
Application number: PCT/JP2018/022686
Authority: WO
Inventors: 篤生小林; 英彦山口; 原　智章
Original assignee: Dic株式会社
Priority date: 2017-06-23
Filing date: 2018-06-14
Publication date: 2018-12-27
Also published as: CN110719948A; JP6489397B1; JPWO2018235713A1; CN110719948B

Abstract

Provided are: a liquid crystal composition containing at least one type of hindered amine-based light stabilizer having at least one unpaired electron in the molecules thereof; and a liquid crystal display element using said liquid crystal composition. This crystal composition is stable against heat and light, has a high specific resistance value, and has a high voltage holding ratio (VHR (UV)) after UV irradiation. In addition, a display element using this liquid crystal composition is extremely practical as a liquid crystal composition for liquid crystal displays and can provide excellent display quality having no display defects or suppressed display defects and fast response speed.

Description

Liquid crystal composition and liquid crystal display device using the same

The present invention relates to a liquid crystal composition useful as an electro-optical liquid crystal display material.

Liquid crystal display devices are used in watches, calculators, various measurement devices, panels for automobiles, word processors, electronic notebooks, printers, computers, televisions, watches, advertisement display boards, and the like. Typical liquid crystal display methods are TN (twisted nematic) type, STN (super twisted nematic) type, and VA (vertically aligned) type characterized by vertical alignment using TFT (thin film transistor). And IPS (in-plane switching) type / FFS (fringe field switching) type characterized by horizontal orientation.

In these display modes, IPS type, ECB type (Electrically Controlled Birefringence), VA type, CSH (color super homeotropic) type, etc. use liquid crystal materials showing negative dielectric anisotropy (Δε). It has a feature. On the other hand, in a horizontal alignment type display such as TN type, STN type or IPS type, a liquid crystal composition with a positive Δε is used. In recent years, there has also been reported a driving method in which a liquid crystal composition having a positive Δε is vertically aligned when no voltage is applied, and an IPS type / FFS type electric field is applied to display. Low voltage driving, high speed response, and a wide operating temperature range are required for all of these driving methods. That is, a large absolute value of Δε, a small viscosity (η), and a high nematic phase-isotropic liquid phase transition temperature (T _ni ) are required. In addition, it is necessary to adjust Δn of the liquid crystal composition to an appropriate range in accordance with the cell gap from the setting of Δn × d which is the product of the refractive index anisotropy (Δn) and the cell gap (d). In addition since the high-speed response is emphasized, a small liquid crystal composition having gamma ₁ is required in the case of applying the liquid crystal display device to a television or the like. The liquid crystal composition is generally composed of several to several tens of compounds in order to make Δε, Δn, etc. optimum values for individual display elements.

In addition to the requirements for the physical properties of the liquid crystal composition, the liquid crystal composition used for the liquid crystal display element is required to be stable against external stimuli such as moisture, air, heat, light and the like. If the stability to external stimuli is lost, display defects such as burn-in and display unevenness occur on the liquid crystal display element. In order to suppress display defects such as burn-in and display unevenness, it is generally considered that a high voltage holding ratio (VHR) is essential. Therefore, for example, it is necessary to specify an antioxidant or a light stabilizer It is known to use a liquid crystal composition in combination with a compound of (Patent Document 1 and Patent Document 2). The stability to this external stimulus is important in all applications, and further development of a liquid crystal composition capable of realizing high VHR has been required.

Further, in the liquid crystal composition faster response, such as a liquid crystal television is required, without reducing the Δn and T _ni, sufficiently small eta, sufficiently small gamma _1, to increase the elastic constant (K ₃₃₎ In addition to that, high VHR was required. In addition, there has been a demand for a liquid crystal display element with excellent display quality, which has no or suppressed display defects such as burn-in and display unevenness using this.

JP 2014-84460 JP 2014-84462A

The problem to be solved by the present invention is to provide a liquid crystal composition which is stable against heat and light and can maintain a high voltage holding ratio, and by using this, there is no display defect such as burn-in or display unevenness or It is providing the liquid crystal display element excellent in the display quality which was suppressed.

As a result of examining the various compounds and various compositions in order to solve the problems, the present inventors find that the problems can be solved by using a specific compound, and complete the present invention. It came to

That is, the present invention provides a liquid crystal composition containing one or more hindered amine light stabilizers having one or more unpaired electrons in the molecule.

The liquid crystal composition of the present invention is stable against heat and light and can maintain a high voltage holding ratio, and therefore, by using this for a liquid crystal display element, display defects such as burn-in and display unevenness are not or suppressed. And a liquid crystal display device excellent in display quality.

The liquid crystal composition in the present invention contains one or more hindered amine light stabilizers having one or more unpaired electrons in the molecule.

The hindered amine light stabilizer is preferably a compound represented by the general formula (i) or the general formula (ii).

(Wherein, R ⁱ⁰ represents a hydrogen atom, a hydroxyl group, -O.-, Or an alkyl group having 1 to 20 carbon atoms, and one or more non-adjacent -CH ₂ present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- _{, -C≡C -, - Si (CH} 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl ^group, in ^{R i0} Or one or more hydrogen atoms may be independently substituted with a fluorine atom, a chlorine atom or a cyano group Bur, represents at least one or more ^{R i0} is -O ·,
R ⁱ¹ , R ⁱ² , R ⁱ³ and R ⁱ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, and R ⁱ¹ and R ⁱ² and / or R ⁱ³ and R ⁱ⁴ combine with each other to form a ring You may
R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ and R ⁱ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and when R ⁱ⁵ and R ⁱ⁶ and / or R ⁱ⁷ and R ⁱ⁸ represent an alkyl group And R ⁱ⁵ and R ⁱ⁶ and / or R ⁱ⁷ and R ⁱ⁸ may be bonded to each other to form a ring,
n ⁱ represents 0 or 1 and
m ⁱ¹ represents an integer of 1 to 6, M ⁱ represents a monovalent to hexavalent organic group, the valence number of M ⁱ is the same number as the number represented by m ⁱ , and when there are a plurality of R ⁱ⁰ , Are the same or different, but at least one or more R ⁱ⁰ represents -O ·, and R ⁱ⁰ , R ⁱ¹ , R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ When R ⁱ⁸ and n ⁱ exist in plurality, they may be the same or different. )

(Wherein, R ⁱⁱ⁰ represents a hydrogen atom, a hydroxyl group, -O.-, Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent -CH ₂ present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- _{, -C≡C -, - Si (CH} 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl ^group, in ^{R ii0} Or one or more hydrogen atoms are independently substituted with a fluorine atom, a chlorine atom or a cyano group It may also be, but at least one or more ^{R ii0} represents -O ·,
R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ and R ⁱⁱ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, and R ⁱⁱ¹ and R ⁱⁱ² and / or R ⁱⁱ³ and R ⁱⁱ⁴ combine with each other to form a ring You may
R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ and R ⁱⁱ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and in the case where R ⁱⁱ⁵ and R ⁱⁱ⁶ and / or R ⁱⁱ⁷ and R ⁱⁱ⁸ represent an alkyl group ^And said R ⁱⁱ⁵ and R ⁱⁱ⁶ and / or R ⁱⁱ⁷ and R ⁱⁱ⁸ may be bonded to each other to form a ring,
n ⁱⁱ represents 0 or 1;
m ⁱⁱ represents from 1 4, U ⁱⁱ represents 2 × m ⁱⁱ valent organic group that forms a ring structure, if R ⁱⁱ⁰ there are a plurality, they may be different even identical, At least one or more R ⁱ⁰ represents -O ·, and when there are a plurality of R ⁱⁱ⁰ , R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ , R ⁱⁱ⁴ , R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ , R ⁱⁱ⁷ and n ⁱⁱ , when they exist, May be the same or different. )
In the general formula (i) and the general formula (ii), when m ⁱ and m ⁱⁱ represent 1, R ⁱ⁰ and R ⁱⁱ⁰ represent -O. If m ⁱ and ^{m ii} is a number from 2 or more, ^{R i0} and ^{R ii0} there are a plurality, preferably at least one or more represents -O ·, be more than one represents -O · Preferred However, from the viewpoint of improving VHR, it is preferable that all of the plurality of R ⁱ⁰ and R ⁱⁱ⁰ do not represent -O. That is, at least one of R ⁱ⁰ and R ^{ii 0} represents hydrogen, a hydroxyl group or an alkyl group having 1 to 20 carbon atoms, whereby the hydrogen, the hydroxyl group or the alkyl group having 1 to 20 carbon atoms is a liquid crystal composition It is thought that it is for supplementing the radicals inside.

m ⁱ and ^{m ii} represents a number greater than 2, ^{if R i0} and ^{R ii0} there are a plurality represents a -O · and -O · non groups, groups other than -O ·, the phase of the liquid crystal composition From the viewpoint of solubility, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms is preferable, and More preferably, it is an alkyl group, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 3 to 12 carbon atoms. The alkyl group, alkoxy group or alkenyl group is preferably linear or molecular, and preferably linear. From the viewpoint of simplicity of preparation, a hydrogen atom or a linear alkyl group of 1 to 5 carbon atoms is particularly preferable. Further, in order to enhance the photodegradation preventing ability, a hydrogen atom or a hydroxyl group is preferable, and a hydrogen atom is particularly preferable.

R ⁱ¹ , R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ and R ⁱⁱ 4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and the availability of raw materials and From the viewpoint of the stability of the compound, a methyl group is particularly preferred. Further, in order to facilitate removal of polar impurities mixed during production, R ⁱ¹ and R ⁱ² and / or R ⁱ³ and R ⁱ⁴ are preferably bonded to each other to form a ring structure. Similarly, it is preferable that R ⁱⁱ¹ and R ⁱⁱ² and / or R ⁱⁱ³ and R ⁱⁱ⁴ be bonded to each other to form a ring structure.

R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ and R ⁱⁱ⁸ are preferably each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and a hydrogen atom or It is preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or a methyl group from the viewpoint of the availability of the raw material and the stability of the compound.

In the compound represented by the general formula (i), m ⁱ is an integer of 1-6, M ⁱ represents 1 to hexavalent organic group, as many valence of M ⁱ is represented by n ⁱ It is.

M ⁱ is preferably a group represented by general formula (i-M).

(Wherein, Z ^M1 and Z ^M2 are each independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO 2 -, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -SCH _2- , -CH ₂ S-, -CF ₂ O- _{_{_{, -OCF 2 -, - CF 2}}} S -, - SCF 2 -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - _{_{_{, - - COO-CH 2 CH}}} 2 OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH ₂ -COO-, -CH ₂ -OCO-, -CH = CH-, -N = N-, -CH = N-, -N = CH-, -CH = N-N = CH-, -CF = CF-, -C≡C- or a single bond,
A ^M1 is (a) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- .)
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
Group (a), group (b) and group (c) are each independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, Nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group or alkyl having 1 to 12 carbon atoms And one or more non-adjacent two or more -CH _2- which may be substituted with one or more groups in the alkyl group are each independently -O-, -S-, -CO-, -COO -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH OCO -, - COO-CH = CH -, - OCO-CH = CH -, - CH = CH -, - CF = CF -, - OCF 2 -, - substituted with _CF 2 O-or -C≡C- May be
Sp ^M1 represents a single bond or an alkylene group having 1 to 10 carbon atoms, and one or two or more non-adjacent -CH _2- present in the alkylene group to Z ^M1 adjacent to Sp ^M1 Each of -CH ₂ -which is not directly bonded is independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- or -O-CO- O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH—, —CF = CF—, —OCF ₂ —, —CF ₂ O—, or —C≡C— may be substituted,
W represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, an amino group, a hydroxyl group, a mercapto group or a monovalent to hexavalent organic group. Is the same number as that represented by ^mi1 in the general formula (i),
pM1 represents an integer of 0 to 8,
nM1 represents an integer of 1 ~ 6, ^{m i1} in nM1 and general formula (i) is the same number,
If ^Z ^{^M1,} Z M2, ^Sp ^M1 and ^{A M1} there are multiple, they may be different even in the same. )
In the general formula (i-M), Z ^M1 and Z ^M2 are —CH ₂ O—, —COO—, —OCO—, —CO—NH—, —COO—CH = CH—, from the viewpoint of ease of preparation. _{_{_{-COO-CH 2 CH 2 -,}}} - COO-CH 2 -, - CH 2 -OCO -, - CH = CH -, - preferably C≡C- or a single bond, _-CH 2 O -, - More preferably, it is COO-, -CO-NH- or a single bond.
Sp ^M1 is preferably a single bond or an alkylene group having 1 to 8 carbon atoms, more preferably a single bond or an alkylene group having 1 to 6 carbon atoms, and one or more present in the alkylene group nonadjacent two or more -CH ₂ - in, -CH ₂ is not directly bonded to ^{Z M1} adjacent to ^{Sp M1} - are each independently -O -, - COO -, - OCO -, - CH = It may be substituted by CH- or -C≡C-. Sp ^M1 is preferably a single bond in view of the availability of raw materials and the ease of synthesis.

A ^M1 is 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4 -Diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group is preferred, and these groups are each independently It is preferably unsubstituted, and may be substituted with a cyano group, a fluorine atom, a chlorine atom, a methyl group or a methoxy group.

In general formula (i-M), a structure containing -OO-, -NH-O-, -O-NH-, -O-S- and -SO- group will not be obtained.

pM1 is preferably an integer of 0 to 3, and preferably an integer of 1 to 3, from the viewpoint of compatibility with the liquid crystal composition and easiness of production.
nM1 represents the same number ^{m i1} in the general formula (i). W is preferably a hydrogen atom or a monovalent to tetravalent organic group, but the valence of W is the same as the number represented by ^mi1 in the general formula (i). For example, when m ⁱ¹ in the general formula (i) represents 1, that is, when nM1 in the general formula (i-M) is 1 and the valence of W is 1, the general formula (i-M) is

Represents ^{If m i1} in the general formula (i) is 2, i.e., the general formula (i-M) nM1 in is 2 and the valence of W is 2, the general formula (i-M) is

Represents

In the general formula (i), when m ⁱ¹ in the general formula (i) represents 1, that is, when nM 1 in the general formula (i-M) is 1 and the valence of W is 1, the general formula W in (i-M) is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, an amino group, a hydroxyl group, a mercapto group or an alkyl having 1 to 12 carbon atoms It is preferable to represent a group, and one or two or more non-adjacent -CH _2- present in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO -, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF _{CF -, - OCF 2 -,} - CF 2 O-, or may be substituted by -C≡C-. From the viewpoint of easiness of production, W preferably represents an alkyl group having 1 to 8 carbon atoms. The alkyl group may be linear or branched, but is preferably linear.

In the general formula (i), when m ⁱ¹ in the general formula (i) represents 2, that is, when the nM1 in the general formula (i-M) is 2 and the valence of W is 2, the general formula W in (i-M) is preferably an alkylene group having 1 to 10 carbon atoms, and one or two or more non-adjacent -CH _2- present in the alkylene group are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH- CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF-, -OCF ₂ -, -CF ₂ O-, or -C≡C- may be substituted.

Also, ^{if m i1} in the general formula (i) is 2, i.e., NM1 in formula (i-M) is 2, if the valence of W is 2, W is (a) 1, 4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
And the group (a), the group (b) and the group (c) each independently represent a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a pentafluorosulfura group. Nyl, Nitro, Cyano, Isocyano, Amino, Hydroxyl, Mercapto, Methylamino, Dimethylamino, Diethylamino, Diisopropylamino, Trimethylsilyl, Dimethylsilyl, Thioisocyano or One or two non-adjacent -CH _2- which may be substituted by 12 alkyl groups in the alkyl group are each independently -O-, -S-, -CO- , -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO- -CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - CH = CH -, - CF = CF -, - OCF 2 -, - CF 2 O-, or -C ≡C- may be substituted.

When W has a valence of 2, W in the general formula (i-M) is preferably an alkylene group having 1 to 8 carbon atoms, and more preferably an alkylene group having 1 to 6 carbon atoms, The alkylene group may be linear or branched, but is preferably linear. In addition, one or two or more non-adjacent -CH _2- present in the alkylene group are each independently -O-, -COO-, -OCO-, -CH = CH- or -C. It may be substituted by ≡C-. W is 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1, It is preferable to represent 4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group, and these groups are each independently It is preferably unsubstituted, and may be substituted with a cyano group, a fluorine atom, a chlorine atom, a methyl group or a methoxy group.

In the general formula (i), when m ⁱ¹ in the general formula (i) represents 3, that is, when nM 1 in the general formula (i−M) is 3 and the valence of W is 3, the general formula It is preferable that W in (i-M) represents a hydrocarbon group having 1 to 15 carbon atoms, and one or two or more non-adjacent -CH present in carbon atoms in the hydrocarbon group. ₂ -is each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO- NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = _{CF -, - OCF 2 -,} - CF 2 O-, or may be substituted with -C≡C-. W is more preferably a group selected from the groups represented by Formula (W3-1) to Formula (W3-12).

( ^Wherein , R ^w31 and R ^{w32 each} represent a hydrogen atom, a hydroxyl group or an alkyl group having 1 to 10 carbon atoms, and one or more -CH _2- present in the alkyl group are each independently It may be substituted by -O-, -S-, -CH = CH-, -C≡C-, -CO-O- or -O-CO-, and the hydrogen atom in the cyclic structure is fluorine Atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group And trimethylsilyl group, dimethylsilyl group, thioisocyano group or an alkyl group having 1 to 12 carbon atoms, which may be substituted or absent in the alkyl group Two or more -CH ₂ -are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO- O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = It may be substituted with CH-, -CF = CF-, -OCF _2- , -CF ₂ O-, or -C≡C-).
^Each of R ^w31 and R ^w32 preferably represents a hydrogen atom, a hydroxyl group or an alkyl group having 1 to 8 carbon atoms, and is preferably linear. In addition, it is preferable that Formula (W3-4) to Formula (W3-12) are each independently unsubstituted, and a hydrogen atom in Formula (W3-4) to Formula (W3-12) is a cyano group It may be substituted by a fluorine atom, a chlorine atom, a methyl group or a methoxy group.

Represents a group selected from Formula (W3-1), Formula (W3-2), and non-substituted Formulas (W3-3) to (W3-12) from the viewpoint of availability of raw materials and easiness of production Is particularly preferred.

Specifically, compounds in which m ⁱ¹ represents 3 as general formula (i) are particularly preferably compounds represented by general formulas (i-a1) to (i-a14).

^(R ^{11, R 12} and ^{R 13} in the formulas represents the same meaning as ^{R i0} of independently in the general formula (i).)
In the general formula (i), when m ⁱ¹ in the general formula (i) represents 4, that is, when the nM 1 in the general formula (i-M) is 4 and the valence of W is 4, the general formula It is preferable that W in (i-M) represents a hydrocarbon group having 1 to 15 carbon atoms, and one or two or more non-adjacent -CH present in carbon atoms in the hydrocarbon group. ₂ -is each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO- NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = _{CF -, - OCF 2 -,} - CF 2 O-, or may be substituted with -C≡C-. More preferably, W is a group selected from the groups represented by formulas (W4-1) to (W4-21).

The hydrogen atom in the cyclic structure is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino It may be substituted by a group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group or an alkyl group having 1 to 12 carbon atoms, and one or two adjacent groups in the alkyl group are not present Two or more -CH ₂ -are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO- O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH , -CH = CH -, - CF = CF -, - OCF 2 -, - CF 2 O-, or may be substituted with -C≡C-. In addition, it is preferable that Formula (W4-3) to Formula (W4-21) be each independently unsubstituted, and a hydrogen atom in Formula (W4-3) to Formula (W4-21) is a cyano group. It may be substituted by a fluorine atom, a chlorine atom, a methyl group or a methoxy group.

Represents a group selected from Formula (W4-1), Formula (W4-2), and non-substituted Formulas (W4-3) to (W4-21) from the viewpoint of availability of raw materials and easiness of production Is particularly preferred.

The compound represented by the general formula (i) is preferably a compound represented by the following general formula (i-1).

In the general formula (i-1), R ^is represents the same as R ⁱ⁰ in the general formula (i).

M ^iS represents an alkyl group having 1 to 15 carbon atoms when m ^iS represents 1 and represents an alkylene group having 1 to 15 carbon atoms when m ^iS represents an integer of 2 to 6 and is present in M ^iS At least one of -CH ₂ -is -O-, -CH = CH-, -C≡C-, -CO-, -OCO-, -COO-, trans-1, 4-cyclohexylene group, 1 Although it may be substituted with a 2,4-phenylene group or a naphthalene-2,6-diyl group, in consideration of the viscosity given to the liquid crystal composition and its volatility, M ^iS is an alkyl group having 2 to 10 carbon atoms or An alkylene group is preferable, an alkyl group having 2 to 8 carbon atoms or an alkylene group is preferable, an alkyl group having 4 to 8 carbon atoms or an alkylene group is preferable, and an alkyl group having 6 or 8 carbon atoms or an alkylene group is preferable. M ^iS may be linear or branched.

m ^{i S} represents an integer of 1 to 6, preferably 2 to 4.

When m ^iS represents 1, the compound represented by General Formula (i-1) is preferably a compound represented by General Formula (i-11) or General Formula (i-12).

(Wherein, R ^is represents the same as R ⁱ⁰ in the general formula (i), and M represents an alkylene group having 1 to 13 carbon atoms)

(Wherein, R ^is represents the same as R ⁱ⁰ in General Formula (i), and R ⁱ¹¹ independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.)
When m ^iS represents 2, the compound represented by General Formula (i-1) is preferably a compound represented by General Formula (i-2).

(Wherein, R ^H1 and R ^H2 each represent the same meaning as R ⁱ⁰ in the general formula (i), M represents an alkylene group having 1 to 15 carbon atoms, and one or more present in M -CH ₂ -is -O-, -CH = CH-, -C≡C-, -CO-, -OCO-, -COO-, trans-1, 4-cyclohexylene group, 1,4-phenylene group , Naphthalene-2,6-diyl group may be substituted.)
In the general formula (i-2), M represents an alkylene group having 1 to 15 carbon atoms, but considering the viscosity given to the liquid crystal composition and the volatility of itself, M is an alkylene having 2 to 10 carbon atoms. Preferably, alkylene having 4 to 8 carbon atoms is preferable, and alkylene having 6 or 8 carbon atoms is preferable.
Specifically, compounds represented by general formula (i-24), general formula (i-26) and general formula (i-28) can be mentioned. R ^H1 and R ^{H2 in} these formulas are as described above.

When m ^iS represents an integer of 3 to 6, the compound represented by General Formula (i-1) is preferably a compound represented by General Formula (i-3).

(Wherein, R ^H3 , R ^H4 and R ^H5 each independently represent the same as R ⁱ⁰ in General Formula (i), and n ^H1 and n ^H2 each independently represent 0 or 1. n ^H3 represents an integer of 1 to 4. When n ^H3 is 2, 3 or 4, and there are a plurality of R ^H5 , they may be the same or different.)
In the general formula (i-3), when n ^H3 represents 1, it is preferable to represent the general formula (i-a1) to the general formula (i-a3). In the general formula (i-3), when n ^H3 represents 2, compounds represented by the following general formula (i-31) and the general formula (i-32) are preferable. R ^H3 , R ^H4 and R ^{H5 in} these formulas are as described above.

Examples of the compound n ⁱ represents 0 in the compound represented by the general formula (i), the following compounds are preferred.

^{(R 10} in the formula has the same meaning as ^{R i0} in the general formula (i).)
As the compound represented by General Formula (ii), a compound represented by the following General Formula (ii-1) or General Formula (ii-2) is preferable.

^{(Wherein, R II 10} has the same meaning as ^{R ii0} in general formula (ii), there may
Sp ⁱⁱ¹ represents a single bond or an alkylene group having a carbon number of from 12, one -CH ₂ present in the alkylene group - or nonadjacent two or more -CH ₂ - is -O -, - It may be replaced by COO-, -OCO-, -CH = CH- or -C≡C-,
A ⁱⁱ¹ each independently represents (a) 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more non-adjacent —CH ₂ — replaced by —O— May be
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
Group (a), group (b) and group (c) are each independently substituted with a cyano group, a fluorine atom, a chlorine atom, a methyl group or a methoxy group And R ⁱⁱ¹¹ is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a group represented by the general formula (i-e)

(Wherein, R ^e1 represents a hydrogen atom or a hydroxyl group, Sp ^ie1 represents a single bond or an alkylene group having 1 to 12 carbon atoms, and one —CH ₂ — or adjacent group present in the alkylene group And two or more -CH ₂ -may be replaced by -O-, -COO-, -OCO-, -CH = CH- or -C≡C-, and s 1 represents 0 or 1.)
And one or more -CH _2- or two or more non-adjacent -CH _2- present in R ^{ii 11} are -O-, -S-, ^-COO- , ^-OCO- , -CO-, -CH = CH- or -C≡C-, may be replaced by
n ⁱⁱ¹ represents 0 or ^{1, p ii} each represents 0, 1, or ^{2, if p ii} represents 2, optionally substituted by one or more identical ^{Sp ii1} and ^{A ii2} there are a plurality each independently It is also good. )

( ^Wherein , R ⁱⁱ¹⁰ and R ^{ii 21 each} represent a hydrogen atom, a hydroxyl group, ^-O.- , Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent ones present in the alkyl group -CH ₂ -is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO -O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH CHCH-, -C≡C-, -Si (CH ₃ ) _2- , trans 1,4-cyclohexylene group, 1,4-phenylene group or naphthalene-2,6-diyl group may be substituted, one or more hydrogen atoms are each independently fluorine atoms in R ^ii0, chlorine atom or cyano In may be ^substituted, at least one of ^{R Ii20} and ^{R Ii21} represent -O ·,
n ⁱⁱ² , l, o and r each independently represent 0 or 1; )
In addition, the hindered amine light stabilizer having one or more unpaired electrons in the molecule is a compound represented by the following general formula (i-N) or general formula (ii-N) preferable.

(Wherein, R ^iN represents a hydrogen atom, a hydroxyl group, -O.-, Or an alkyl group having 1 to 20 carbon atoms, and one or more non-adjacent -CH ₂ present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- _{, -C≡C -, - Si (CH} 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl ^group, in ^{R i0} Or one or more hydrogen atoms may be independently substituted with a fluorine atom, a chlorine atom or a cyano group Bur, in the general formula (iN), it has at least one or more nitrogen atoms are unpaired electrons, if the nitrogen atom has an unpaired electron is = N-R ^iN represents = N ·,
R ⁱ¹ , R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁷ , R ⁱ⁸ , n ⁱ , m ⁱ¹ and M ⁱ are R ⁱ¹ , R ⁱ² , R ⁱ³ and R ⁱ in the general formula (i) ^The same meanings as ^{i 4} , R ^{i 5} , R ⁱ ⁶ , R ^{i 7} , R ^{i 8} , n ⁱ , m ⁱ¹ and M ⁱ respectively are indicated. )

( ^Wherein , R ^iiN represents a hydrogen atom, a hydroxyl group, ^-O.- , Or an alkyl group having 1 to 20 carbon atoms, and one or more non-adjacent -CH ₂ present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- _{, -C≡C -, - Si (CH} 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl ^group, in ^{R ii0} Or one or more hydrogen atoms are independently substituted with a fluorine atom, a chlorine atom or a cyano group May, but in general formula (IIN), has at least one or more nitrogen atoms are unpaired electrons, if the nitrogen atom has an unpaired electron is = N-R ^IIN represents = N · ,
R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ , R ⁱⁱ⁴ , R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ , R ⁱⁱ⁸ , R ⁱⁱ⁸ , N ⁱⁱ , ^M ⁱⁱ and U ⁱⁱ are R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ and R ⁱⁱ in the general formula (ii) ^{^{^{^{ii4, R ii5, R ii6,}}}} R ii7, R ii8, n ii, respectively ^{m ii} and ^{U ii} represent the same meaning. )
The liquid crystal composition used in the liquid crystal display element is exposed to light and / or heat in a process such as curing of a sealing agent for sealing the liquid crystal composition at the time of production of the liquid crystal display element. Moreover, the liquid crystal display element after manufacture is also exposed to light and put in the environment under high temperature. These external stimuli deactivate the liquid crystal compound and subsequently cleave it to generate radicals. The generated radical compound causes an addition reaction to generate ions, so that these reaction products are present in a large amount as impurities in the liquid crystal composition. As a result, the stability of the liquid crystal composition is impaired, which is considered to lead to the deterioration of the quality of the liquid crystal display element. On the other hand, when a hindered amine light stabilizer is added to the liquid crystal composition, the liquid crystal composition having higher stability can be obtained by the action of reducing the amount of the radical compound by capturing the radical compound generated in the liquid crystal composition. It is thought that you can get things.
In particular, hindered amine light stabilizers having one or more unpaired electrons in the molecule have unpaired electrons, and thus, for example, R ⁱ⁰ in general formula (i) or in general formula (ii) Since R ⁱⁱ⁰ is a group having no hydrogen atom, it does not release a causative substance (by-product) of an ion such as hydrogen when supplementing the generated radical compound. Since the released by-product causes the reduction of the specific resistance value, it is considered that the reduction of the specific resistance value can be further suppressed by using the hindered amine light stabilizer of the present invention.
Generally, radical compounds are considered to be unstable and change to stable compounds. However, hindered amine light stabilizers having one or more unpaired electrons in the molecule of the present invention have ESR (Electron Spin Resonance). ) Was confirmed to be a stable compound. Furthermore, since the hindered amine light stabilizer having unpaired electrons is drawn to the alignment film, it has been confirmed by ESR that deterioration of the alignment film can be suppressed.

In the liquid crystal composition of the present invention, the total content of hindered amine light stabilizers having one or more unpaired electrons in the molecule is preferably contained in the composition as a lower limit of 0.001% or more. It is preferable to contain 0.002% or more, preferably 0.003% or more, preferably 0.004% or more, and preferably 0.005% or more, 0.006% or more. It is preferably contained, preferably 0.007% or more, preferably 0.008% or more, preferably 0.009% or more, and more preferably 0.01% or more, The content is preferably 0.02% or more, preferably 0.03% or more, preferably 0.04% or more, and preferably 0.05% or more. Is preferably contained, preferably 0.06% or more, more preferably 0.07% or more, preferably 0.08% or more, and more preferably 0.09% or more. The content is preferably 10% or more, preferably 0.11% or more, preferably 0.12% or more, preferably 0.13% or more, and preferably 0.14% or more. Is preferably contained, the content is preferably 0.20% or more, the content is preferably 0.25% or more, the content is preferably 0.30% or more, and 0.35 % Content is preferable, 0.40% or more content is preferable, 0.50% or more content is preferable, and 1% or more content is preferable. The upper limit thereof is preferably 5% or less, preferably 3% or less, more preferably 2% or less, and preferably 1.5% or less, preferably 1% or less. It is preferable to contain 0.9% or less, preferably 0.8% or less, preferably 0.7% or less, and preferably 0.6% or less. It is preferable to contain the following, preferably to contain 0.45% or less, preferably to contain 0.4% or less, preferably to contain 0.35% or less, and preferably to contain 0.3% or less The content is preferably 0.25% or less, preferably 0.2% or less, preferably 0.15% or less, and preferably 0.1% or less, 0.07 Preferably contains less, preferably it contains more than 0.05%, and preferably 0.03% or less.

More specifically, the content is preferably 0.01 to 2% by mass, preferably 0.01 to 1% by mass, still more preferably 0.01 to 0.2% by mass, 0. It is particularly preferable that the content be from 01 to 0.15% by mass. More specifically, the content is preferably 0.01 to 0.1% by mass when importance is placed on the suppression of precipitation at low temperatures.

The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (II).

(Wherein, R ^II1 represents an alkyl group having 1 to 10 carbon atoms, and one or two non-adjacent —CH ₂ — in the alkyl group are each independently —CH = CH—, — It may be substituted by C≡C-, -O-, -CO-, -COO- or -OCO-,
A ^II1 and A ^II2 are each independently (a) 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more non-adjacent —CH ₂ — is —O And-(b) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = replaced by -N = May be
(C) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or One —CH = or two or more non-adjacent —CH = present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by —N =. )
And the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^II1 is a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —OCF ₂ —, —CF ₂ O— , -CH = N-N = CH-, -CH = CH-, -CF = CF- or -C≡C-,
Y ^II1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent -CH ₂ -in the alkyl group are each independently Optionally substituted by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or more hydrogens in the alkyl group The atom may be substituted by a fluorine atom,
Although m ^II1 represents 1, 2, 3 or 4, when m ^II1 represents 2, 3 or 4, two or more A ^II1 and Z ^II1 may be the same or different. )
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (II) is preferably 10% or more, preferably 30% or more, as the lower limit value in the composition, 50 % Is preferable, 80% or more is preferable, 85% or more is preferable, 88% or more is preferable, 90% or more is preferable, and 92% or more is preferable. Is preferably 95% or more, preferably 97% or more, preferably 98% or more, preferably 99% or more, and substantially substantially a hindered amine light stabilizer And it is preferable not to contain other compounds other than a polymeric compound. Further, the upper limit thereof is preferably 90% or less, preferably 95% or less, preferably 98% or less, and preferably 99% or less, and substantially hindered amine light stabilizer And it is preferable not to contain other compounds other than a polymeric compound. Substantially means that the compound which is unintentionally contained, such as an impurity produced unavoidable at the time of manufacture, is removed.
<First Embodiment of Compound Represented by General Formula (II)>
The compound represented by the general formula (II) is a so-called p-type liquid crystal compound having a positive dielectric anisotropy and can be a compound represented by the following general formula (J).

As a compound represented by General formula (II), it is preferable to contain the compound represented by General formula (J) 1 type or 2 types or more. These compounds correspond to dielectrically positive compounds (Δε is greater than 2).

(Wherein, R ^J1 represents an alkyl group having 1 to 8 carbon atoms, and one or two non-adjacent -CH ₂ -in the alkyl group are each independently -CH = CH-,- It may be substituted by C≡C-, -O-, -CO-, -COO- or -OCO-,
n ^J1 represents 0, 1, 2, 3 or 4;
A ^J1 , A ^J2 and A ^J3 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
Group (a), group (b) and group (c) are each independently a cyano group, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group or a trifluoro group It may be substituted by a methoxy group,
Z ^J1 and Z ^J2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents -COO-, -OCO- or -C≡C-,
When n ^J1 is 2, 3 or 4 and there are a plurality of A ^J2 , they may be the same or different, and n ^J1 is 2, 3 or 4 and a plurality of Z ^J1 is present If they are identical or different,
X ^J1 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. )
In the general formula (J), R ^J1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy having 2 to 8 carbon atoms Group is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group of 1 to 5 or an alkenyl group of 2 to 5 carbon atoms is further preferable, an alkyl group of 2 to 5 carbon atoms or an alkenyl group of 2 to 3 carbon atoms is further preferable, and an alkenyl group of 3 carbon atoms (Propenyl group) is particularly preferred.

When importance is attached to reliability, R ^J1 is preferably an alkyl group, and when importance is attached to decrease in viscosity, it is preferably an alkenyl group.

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

The alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in a ring structure to which an alkenyl group is bonded.)

A ^J1 , A ^J2 and A ^J3 are each preferably aromatic when it is required to increase Δn independently, and in order to improve the response speed, it is preferably aliphatic; 1,4-cyclohexylene group, 1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene -2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferred, and they are substituted by a fluorine atom It is more preferable to represent the following structure.

It is more preferable to represent the following structure.

Z ^J1 and Z ^J2 each preferably independently represent -CH ₂ O-, -OCH _2- , -CF ₂ O-, -CH ₂ CH _2- , -CF ₂ CF ₂ -or a single bond,- More preferred is OCH ₂ —, —CF ₂ O—, —CH ₂ CH ₂ — or a single bond, and particularly preferred is —OCH ₂ —, —CF ₂ O— or a single bond.

X ^J1 is preferably a fluorine atom or a trifluoromethoxy group, more preferably a fluorine atom.

n ^J1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, 0 or 1 if emphasis is placed on improvement of Δε, and 1 or 2 if emphasis is placed on Tni .

There is no particular limitation on the types of compounds that can be combined, but they are used in combination according to the desired properties such as low temperature solubility, transition temperature, electrical reliability, birefringence and the like. The types of compounds to be used are, for example, one type, two types, and three types in one embodiment of the present invention. Furthermore, in another embodiment of the present invention, there are four types, five types, six types, and seven or more types.

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

The lower limit of the preferable content of the compound represented by the general formula (J) to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is, for example, 95%, 85%, 75%, 65%, 55% in one form of the present invention based on the total amount of the composition of the present invention Yes, 45%, 35%, 25%.

It is preferable to keep the viscosity of the composition of the present invention low and lower the above lower limit and lower the upper limit when a composition having a high response speed is required. Furthermore, it is preferable to keep the Tni of the composition of the present invention high, and lower the above lower limit and lower the upper limit when a composition having good temperature stability is required. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable to raise the lower limit and raise the upper limit.

As a compound represented by General formula (J), the compound represented by General formula (M) and the compound represented by General formula (K) are preferable.

The composition of the present invention preferably contains one or two or more compounds represented by General Formula (M). These compounds correspond to dielectrically positive compounds (Δε is greater than 2).

(Wherein, R ^M1 represents an alkyl group having 1 to 8 carbon atoms, and one or two non-adjacent -CH ₂ -in the alkyl group are each independently -CH = CH-,- It may be substituted by C≡C-, -O-, -CO-, -COO- or -OCO-,
n ^M1 represents 0, 1, 2, 3 or 4 and
A ^M1 and A ^M2 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S- And (b) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =)
And hydrogen atoms on the above groups (a) and (b) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^M1 and Z ^M2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents -COO-, -OCO- or -C≡C-,
When n ^M1 is 2, 3 or 4 and there are a plurality of ^{AM 2} , they may be the same or different, and n ^M1 is 2, 3 or 4 and a plurality of Z ^M1 is present If they are identical or different,
X ^M1 and X ^M3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom,
X ^M2 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. )
In the general formula (M), R ^M1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy having 2 to 8 carbon atoms Group is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group of 1 to 5 or an alkenyl group of 2 to 5 carbon atoms is further preferable, an alkyl group of 2 to 5 carbon atoms or an alkenyl group of 2 to 3 carbon atoms is further preferable, and an alkenyl group of 3 carbon atoms (Propenyl group) is particularly preferred.

When importance is attached to reliability, R ^M1 is preferably an alkyl group, and when importance is attached to decrease in viscosity, it is preferably an alkenyl group.

A ^M1 and A ^M2 are each preferably aromatic when it is required to increase Δn independently, and in order to improve the response speed, it is preferably aliphatic, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2 ,, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It is preferable to represent a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferable to represent the following structure,

It is more preferable to represent the following structure.

Z ^M1 and ^{Z M2} each _{independently} _{-CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _-CF 2 O-, More preferred is —CH ₂ CH ₂ — or a single bond, with —CF ₂ O— or a single bond being particularly preferred.

n ^M1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, 0 or 1 if emphasis is placed on improvement of Δε, and 1 or 2 if emphasis is placed on Tni .

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

The lower limit of the preferable content of the compound represented by the formula (M) to the total amount of the composition of the present invention is 0%, 1%, 10%, 20%, 30 %, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is, for example, 95%, 85%, 75%, 65%, 55% in one form of the present invention based on the total amount of the composition of the present invention Yes, 45%, 35%, 25%.

Specifically, the liquid crystal compound represented by Formula (M) is preferably the following Formula (M-1) and Formula (M-2).

(Wherein, R ³¹ represents an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 2 to 5 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms, and X ³¹ and X ³² each independently represent hydrogen) Y ³¹ represents a fluorine atom or OCF ₃ , and M ³¹ to M ³³ each independently represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or two -CH ₂ -in the trans-1,4-cyclohexylene group may be substituted by -O- such that the oxygen atom is not directly adjacent, one or two of the phenylene group Two hydrogen atoms may be substituted by fluorine atoms, n ³¹ and n ³² each independently represent 0, 1 or 2, and n ⁴¹ + n ⁴² represent 1, 2 or 3.)
Specifically, 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 the general formula (M-1-f).

^{^{^{(Wherein, R 31, X 31, X}}} 32 and ^{Y 31} are as defined ^R ^{^31, X} ^31, X ³² and ^{Y 31} in the general formula ^{^{(M), X 34 ~ X}} 39 are each independently Represents a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by Formula (M-2) is preferably a compound represented by the following Formula (M-2-a) to Formula (M-2-n).

^{^{^{(Wherein, R 31, X 31, X}}} 32 and ^{Y 31} are as defined ^R ^{^31, X} ^31, X ³² and ^{Y 31} in the general formula ^{^{(M), X 34 ~ X}} 39 are each independently Represents a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by the general formula (M) is preferably the following general formula (M-3) to the general formula (M-26).

^{^{^{(Wherein, R 31, X 31, X}}} 32 and ^{Y 31} are as defined ^R ^{^31, X} ^31, X ³² and ^{Y 31} in the general formula ^{^{(M), X 34 ~ X}} 39 are each independently Represents a hydrogen atom or a fluorine atom)
The composition of the present invention preferably contains one or more compounds represented by General Formula (K). These compounds correspond to dielectrically positive compounds (Δε is greater than 2).

(Wherein, R ^K1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH-CH—, — It may be substituted by C≡C-, -O-, -CO-, -COO- or -OCO-,
n ^K1 represents 0, 1, 2, 3 or 4;
A ^K1 and A ^K2 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S- And (b) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =)
And hydrogen atoms on the above groups (a) and (b) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^K1 and Z ^K2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents -COO-, -OCO- or -C≡C-,
When n ^K1 is 2, 3 or 4 and there are a plurality of ^{AK 2} , they may be the same or different, and n ^K1 is 2, 3 or 4 and a plurality of Z ^K1 is present If they are identical or different,
X ^K1 and X ^K3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom,
X ^K2 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. )
In the general formula (K), R ^K1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy having 2 to 8 carbon atoms Group is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group of 1 to 5 or an alkenyl group of 2 to 5 carbon atoms is further preferable, an alkyl group of 2 to 5 carbon atoms or an alkenyl group of 2 to 3 carbon atoms is further preferable, and an alkenyl group of 3 carbon atoms (Propenyl group) is particularly preferred.

When importance is attached to reliability, R ^K1 is preferably an alkyl group, and when importance is attached to decrease in viscosity, it is preferably an alkenyl group.

A ^K1 and A ^K2 are each preferably aromatic when it is required to increase Δn independently, and is preferably aliphatic to improve the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2 ,, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It is preferable to represent a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferable to represent the following structure,

It is more preferable to represent the following structure.

Z ^K1 and ^{Z K2} are each _{independently} _{-CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _-CF 2 O-, More preferred is —CH ₂ CH ₂ — or a single bond, with —CF ₂ O— or a single bond being particularly preferred.

n ^K1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2; 0 or 1 is preferred when emphasis is placed on improvement of Δε, and 1 or 2 is preferred when emphasis is placed on Tni .

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

The lower limit of the preferable content of the compound represented by the formula (K) to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is, for example, 95%, 85%, 75%, 65%, 55% in one form of the present invention based on the total amount of the composition of the present invention Yes, 45%, 35%, 25%.

Specifically, the liquid crystal compound represented by Formula (K) is preferably the following Formula (K-1) and Formula (K-2).

(Wherein, R ⁴¹ represents an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 2 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and X ⁴¹ and X ⁴² each independently represent hydrogen) Y ⁴¹ represents a fluorine atom or OCF ₃ , and M ⁴¹ to M ⁴³ each independently represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group; One or two -CH ₂ -in the trans-1,4-cyclohexylene group may be substituted by -O- such that the oxygen atom is not directly adjacent, one or two of the phenylene group The two hydrogen atoms may be substituted with a fluorine atom, n ⁴¹ and n ⁴² each independently represent 0, 1 or 2, and n ⁴¹ + n ⁴² represent 1, 2 or 3.)
Specifically, 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 the general formula (K-1-d).

^{^{^{(Wherein, R 41, X 41, X}}} 42 and ^{Y 41} are as defined ^R ^{^41, X} ^41, X ⁴² and ^{Y 41} in the general formula ^{^{(K), X 44 ~ X}} 49 are each independently Represents a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by the general formula (K-2) is preferably a compound represented by the following general formula (K-2-a) to the general formula (K-2-g).

^{^{^{(Wherein, R 41, X 41, X}}} 42 and ^{Y 41} are as defined ^R ^{^41, X} ^41, X ⁴² and ^{Y 41} in the general formula ^{^{(K), X 44 ~ X}} 49 are each independently Represents a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by the general formula (K) is preferably the following general formula (K-3) to the general formula (K-5).

^{^{^{(Wherein, R 41, X 41, X}}} 42 and ^{Y 41} are as defined ^R ^{^41, X} ^41, X ⁴² and ^{Y 41} in the general formula ^{^{(K), X 44 ~ X}} 49 are each independently Represents a hydrogen atom or a fluorine atom)
<Second Embodiment of Compound Represented by General Formula (II)>
The compound represented by the general formula (II) is a so-called n-type liquid crystal compound having a negative dielectric anisotropy, and it is possible to cite compounds represented by the following general formula (LC1) and the general formula (LC2) it can.

It is preferable that the compound represented by the general formula (II) contains one or more compounds selected from the group of compounds represented by the general formulas (N-1) to (N-3).

(Wherein, R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two non-adjacent ones in the alkyl group Or more of -CH ₂ -may be each independently substituted by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each independently (a) 1,4-cyclohexylene group (one —CH ₂ — or adjacent group present in this group Not more than two -CH _2- may be replaced by -O-.)
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
And the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
^{^{^{^{Z N11, Z N12, Z N21}}}} , Z N22, Z N31 and ^{Z N32} are each independently a single _{_{_{_{bond, -CH 2 CH 2 -, -}}}} (CH 2) 4 -, - OCH 2 -, - CH 2 O- , -COO-, -OCO-, -OCF _2- , -CF ₂ O-, -CH = N-N = CH-, -CH = CH-, -CF = CF- or -C≡C-
X ^N21 represents a hydrogen atom or a fluorine atom,
T ^N31 represents -CH ₂ -or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, but n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are each independently When there are a plurality of A ^N11 to A ^N32 and Z ^N11 to Z ^N32 , they may be the same or different. However, the compounds represented by General Formula (N-1) in General Formula (N-2) and General Formula (N-3) are excluded, and in General Formula (N-3), General Formula (N-2) Excluding the compounds represented by )
The compounds represented by the general formulas (N-1), (N-2) and (N-3) are dielectrically negative compounds (the sign of Δε is negative and its absolute value is larger than 2). Preferably, it is a compound in which Δε is negative and its absolute value is greater than 3.

In the general formulas (N-1), (N-2) and (N-3), R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently have 1 to 8 carbon atoms Alkyl group, alkoxy group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms or alkenyloxy group having 2 to 8 carbon atoms is preferable, and alkyl group having 1 to 5 carbon atoms, the number of carbon atoms An alkoxy group of 1 to 5, an alkenyl group of 2 to 5 carbon atoms or an alkenyloxy group of 2 to 5 carbon atoms is preferable, and an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable. In particular, a combination of a compound in which at least one or more of R ^N11 and R ^N12 represents an alkenyl group and a compound represented by the general formula (I) significantly suppresses the decrease in the voltage holding ratio (VHR). be able to. Similarly, by using a compound in which at least one or more of ^RN21 and ^RN22 represents an alkenyl group in combination with a compound represented by General Formula (I), the decrease in voltage holding ratio (VHR) is significantly suppressed. it can, also, by using in combination with a compound which represents at least one or more alkenyl groups R ^N31 and R ^N32, a compound represented by the general formula (I), the decrease in voltage holding ratio (VHR) Can be significantly reduced.

The alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in the ring structure.)

A ^{N 11} , A ^{N 12} , A ^N ²¹ , A ^N ²² , A ^{N 31} and A ^N ³² are each preferably aromatic when it is required to increase Δn independently, and in order to improve the response speed, it is preferable to use fat Group is preferred, and trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 Be 2,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl Preferred, it is more preferable that represents the following structures,

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

^{^{^{^{Z N11, Z N12, Z N21}}}} , Z N22, Z N31 and ^{Z N32} _-CH 2 each _{independently} _{O -, - CF 2 O -} , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents _{_{an, -CH 2 O -, - CH}} 2 CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

X ^N21 is preferably a fluorine atom.

T ^N31 is preferably an oxygen atom.

n ^{N 11} + n ^{N 12} , n N ²¹ + n N ²² and n ^{N 31} + n ^N ³² are preferably 1 or 2, and combinations in which n ^N ¹¹ is 1 and n ^{N 12} is 0, n ^{N 11} is 2 and n ^{N 12} is 0, n ^A combination in which ^N ¹¹ is 1 and n ^{N 12} is 1, a combination in which n ^{N 11} is 2 and n ^{N 12} is 1, a combination in which n N ²¹ is 1 and n N ²² is 0, n N ²¹ is 2 and n N ²² is A combination of 0, a combination of n ^N31 of 1 and n ^N32 of 0, and a combination of n ^N31 of 2 and n ^N32 of 0 is preferred.

The lower limit of the preferable content of the compound represented by the formula (N-1) to the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

The lower limit of the preferable content of the compound represented by the formula (N-2) to the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

The lower limit of the preferable content of the compound represented by the formula (N-3) to the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.

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

The liquid crystal composition of the present invention preferably contains one or two or more compounds represented by General Formula (N-i-1) as General Formula (N-1).

( ^Wherein , A ⁱ¹¹ , A ⁱ¹² and A ⁱ¹³ each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one present in a 1,4-cyclohexylene group of -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S-, it is one of the hydrogen atoms present in the 1,4-phenylene group, respectively independently may be substituted by a fluorine atom or a chlorine ^{atom, Z i1} is _{_{_{-OCH 2 -, - CH 2 O}}} -, - CF 2 O -, - OCF 2 -, - CH 2 CH 2 - or -CF ₂ CF ₂ - ^{represents, m i11} and ^{m i12} are each independently 0 or ^{^1, R} ^N11, R ^N12 and ^{Z N12} ^{is, ^R} N11, ^R ^N12 and in the general formula (N-1) each independently Represents the same meaning as Z ^{N 12} )
The compound represented by the general formula (N-i-1) is a compound represented by the general formula (N-i-1A), the general formula (N-i-1B) or the general formula (N-i-1C) Is preferred.

(Wherein, R ^N11 , R ^N12 , A ⁱ¹¹ and Z ⁱ¹ each independently represent the same meaning as R ^N11 , R ^N12 , A ⁱ¹¹ and Z ⁱ¹ in the general formula ( ^Ni -1).)

^{^{^{(Wherein, R N11, R N12, A}}} i11, A i12 and ^{Z i1} is, ^R N11 in the general formula (N-i1) ^{^{^{independently,}}} R ^{^N12,} ^A ^i11, A same as ⁱ¹² and ^{Z i1} Represents the meaning.)

( ^Wherein , m ⁱ¹³ represents 1 and R ^N11 , R ^N12 , A ⁱ¹¹ , A ⁱ¹² , A ⁱ¹³ , A ⁱ¹³ , Z ⁱ¹ , Z ⁱ² and m ⁱ¹¹ are each independently in general formula ( ^Ni -1) ^{^{^{^{R N11, R N12, a i11}}}} , a i12, a i13, Z i1, the same meanings as ^{Z i2} and ^{m i11.)}
As the compound represented by the general formula (Ni-1A), compounds represented by the following general formula (Ni-1A-1) to the general formula (Ni-1A-4) are preferable.

(Wherein, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in General Formula (N-i-1).)
The compounds represented by the general formula (Ni-1B) include compounds represented by the following general formula (Ni-1B-1) to general formulas (Ni-1B-7) preferable.

(Wherein, R ^N11 and R ^N122 each independently represent the same meaning as R ^N11 and R ^N12 in general formula (N-i-1).)
The compounds represented by the general formula (N-i-1C) may be compounds represented by the following general formula (N-i-1C-1) to general formulas (N-i-1C-4) It is more preferable that it is a compound represented by general formula (N-i-1C-1) and general formula (N-i-1C-2).

(Wherein, R ^N11 and R ^N122 each independently represent the same meaning as R ⁱ¹ and R ⁱ² in General Formula (i-1).)
The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (i), but the general formula (i-1A), the general formula (i-1B) or the general formula The compound selected from the group of compounds represented by (i-1C) may contain one or more compounds, and may be represented by general formula (i-1A), general formula (i-1B) or general formula (i) Each of the compounds represented by -1 C) may be contained. It is preferable to contain one or two or more types of compounds represented by general formula (i-1A) and general formula (i-1B), and it is more preferable to contain two to ten types.

More specifically, the general formula (i-1A), the general formula (i-1B) and the general formula (i-1C) have the general formula (i-1A-1), the general formula (i-1B-1) and the general formula It is preferable to contain one or two or more compounds selected from the compound group represented by formula (i-1C-1), and a compound represented by general formula (i-1A-1) and a compound represented by general formula (i More preferably, it is a combination of compounds represented by -1B-1).

The liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (N-ii) as general formula (LC3).

( ^Wherein , A ⁱⁱ¹ and A ⁱⁱ² each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one —CH present in the 1,4-cyclohexylene group _Two or more non-adjacent two or more -CH _2- may be replaced by -O- or -S-, and one hydrogen atom present in the 1,4-phenylene group is independently of each other may be substituted by a fluorine atom or a chlorine ^{atom, m ii1} and ^{m ii2} independently represents 1 or ^{2, R N11} and ^{R N12} is, ^{R N11} and in the general formula (N-1) each independently It has the same meaning as R ^{N 12.} )
As the general formula (N-ii-1), it is preferable to contain one or more compounds represented by the general formula (N-ii-1).

^(Wherein, represents the same meaning as R ^{^N11,} R ^N12, ^{A ii1} and ^{m ii1} is ^R N11 in the general formula ^{(N-ii), R N12} , A ii1 and ^{m ii1.)}
The compound represented by General Formula (N-ii-1) is preferably a compound represented by General Formula (N-ii-1A) or General Formula (N-ii-1B).

^{^(Wherein, R} ^N11, R ^N12 and ^{A ii1} have the same meanings as ^R ^{N11, R N12} and ^{A ii1} in formula (ii).)

( ^Wherein , A ^{ii 11} and A ^{ii 11} each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one —CH present in the 1,4-cyclohexylene group _Two or more non-adjacent two or more -CH _2- may be replaced by -O- or -S-, and one hydrogen atom present in the 1,4-phenylene group is independently of each other It may be substituted by a fluorine atom or a chlorine ^{atom, R N11} and ^{R N12} in the general formula (ii) represents the same meaning as ^{R N11} and ^{R N12.)}
As the compound represented by the general formula (N-ii-1A), compounds represented by the following general formula (N-ii-1A-1) and the general formula (N-ii-1A-2) are preferable.

(Wherein, R ^N11 and R ^N12 have the same meaning as R ^N11 and R ^N12 in General Formula (N-ii))
The compounds represented by the general formula (N-ii-1B) include compounds represented by the following general formula (N-ii-1B-1) to the general formula (N-ii-1B-3) preferable.

(Wherein, R ^N11 and R ^N12 have the same meaning as R ^N11 and R ^N12 in general formula (ii))
The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (ii), but the general formula (N-ii-1A) and the general formula (N-ii-1B) 1 or 2 or more types of compounds selected from the compound group represented by these) may be included, and the compound represented by general formula (N-ii-1A) and general formula (N-ii-1B) One or more of each may be contained. It is preferable to contain two to ten compounds represented by the general formula (N-ii-1A) and the general formula (N-ii-1B).

More specifically, the general formula (N-ii-1A) preferably contains one or more compounds selected from the group of compounds represented by the general formula (N-ii-1A-1). Formula (N-ii-1B) contains one or more compounds selected from the group of compounds represented by general formula (N-ii-1B-1) and general formula (N-ii-1B-2) Preferably, it is a combination of the compounds represented by the general formula (ii-1A-1) and the general formula (ii-1B-1).

Further, it is preferable to contain one or two or more compounds represented by the following general formula (LC3-b) as the general formula (N-1).

^(Wherein, ^{^{R N11, R N12, A N11}} , A N12 and ^{Z N11} are each independently the same meaning in the general formula (N-1) and ^{^{^{R N11, R N12, A N11}}} , A N12 and ^{Z N11} ^represents, although ^{X LC3b1 ~} X ^LC3b4 represents a hydrogen atom or a fluorine ^{atom, X LC3b1} and ^{X LC3b2,} or at least one combination of ^{X LC3b3} and ^{X LC3b4} together represents a fluorine ^{atom, m LC3b1} a is 0 or 1 However, in the general formula (LC3-b), the compounds represented by the general formula (i-1) and the general formula (ii) are excluded.)
As general formula (LC3-b), it is preferable to represent the following general formula (LC3-b1) to general formula (LC3-b10).

(Wherein, each of R ^N11 and R ^N12 independently represents the same meaning as R ^N11 and R ^N12 in General Formula (N-1).)
The combination of R ^N11 and R ^N12 is not particularly limited, but both represent an alkyl group, both represent an alkenyl group, one represents an alkyl group, and the other represents an alkenyl group, any one is It is preferable that it represents an alkyl group, the other represents an alkoxy, and any one represents an alkyl group, and the other represents an alkenyloxy group, both represent an alkyl group, and both represent an alkenyl group. It is more preferable to represent.

Further, as the general formula (LC3-b), it is preferable to represent the following general formula (LC3-c).

(Wherein, each of R ^N11 and R ^N12 independently represents the same meaning as R ^N11 and R ^N12 in General Formula (N-1).)
The compound represented by General Formula (N-2) is preferably a compound selected from the group of compounds represented by General Formulas (N-2-1) to (N-2-3).

^{(Wherein, R N211} and ^{R N22} are each independently the same meaning as ^{R N211} and ^{R N22} in the general formula (N-2).)
The compound represented by formula (N-3) is preferably a compound selected from the group of compounds represented by formulas (N-3-1) and (N-3-2).

The compounds represented by formula (N-3-1) are the following compounds.

(Wherein, each of R ^N31 and R ^N32 independently represents the same meaning as R ^N31 and R ^N32 in General Formula (N-3).)
<Third Embodiment of Compound Represented by General Formula (II)>
The fourth component is a so-called nonpolar liquid crystal compound having a dielectric anisotropy of about 0, and may be a compound represented by the following general formula (L).

The composition of the present invention preferably contains one or more compounds represented by General Formula (L). The compounds represented by the general formula (L) correspond to dielectric substantially neutral compounds (the value of Δε is −2 to 2).

(Wherein, R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH ₂ -in the alkyl group are independently of each other -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, which may be substituted,
n ^L1 represents 0, 1, 2 or 3;
A ^L1 , A ^L2 and A ^L3 are each independently (a) 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more non-adjacent —CH ₂ — groups May be replaced by -O-.)
(B) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = may be replaced by -N =) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , And one or more non-adjacent -CH = present in the 3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N =).
And the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^L1 and ^{Z L2} each independently represent a single _{_{_{_{bond, -CH 2 CH 2 -, -}}}} (CH 2) 4 -, - OCH 2 -, - CH 2 O -, - COO -, - OCO -, - OCF 2 _{-, - CF 2 O -,} - CH = N-N = CH -, - CH = CH -, - represents CF = CF- or -C≡C-,
When n ^L1 is 2 or 3 and a plurality of A ^L2 is present, they may be the same or different, and when n ^L1 is 2 or 3 and a plurality of Z ^L3 is present, they may be Are the same as or different from each other, but the compounds represented by Formula (J), Formula (N-1), Formula (N-2) and Formula (N-3) are excluded. )
The compounds represented by formula (L) may be used alone or in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the desired performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like. The type of compound used is, for example, one type in one embodiment of the present invention. Or in another embodiment of the present invention, there are 2 types, 3 types, 4 types, 5 types, 5 types, 6 types, 7 types, 8 types, 9 types and 10 It is more than kind.

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

The lower limit of the preferable content of the compound represented by the formula (L) to the total amount of the composition of the present invention is 0%, 1%, 10%, 20%, 30 %, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit value of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.

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

When reliability is important, both R ^L1 and R ^L2 are preferably alkyl groups, and when importance is given to reducing the volatility of the compound, alkoxy groups are preferable, and viscosity reduction is important When doing, at least one is preferably an alkenyl group.

R ^L1 and R ^L2 are, when the ring structure to which they are bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkyl group having 1 to 4 carbon atoms Alkoxy groups and alkenyl groups having 4 to 5 carbon atoms are preferred, and in the case where the ring structure to which they are attached is a saturated ring structure such as cyclohexane, pyran and dioxane, a straight chain having 1 to 5 carbon atoms is preferred. An alkyl group, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, preferably linear.

In particular, a combination of a compound in which at least one or more of R ^L1 and R ^L2 represents an alkenyl group and a compound represented by the general formula (I) significantly suppresses the decrease in the voltage holding ratio (VHR). be able to.

n ^L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferable to improve the upper limit temperature of the nematic phase, and 1 is preferable to balance them. Moreover, in order to satisfy the characteristics required as a composition, it is preferable to combine compounds of different values.

A ^{L 1} , A ^{L 2} and A ^{L 3} are preferably aromatic when it is required to increase Δn, and are preferably aliphatic to improve the response speed, and each of them is independently trans- 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group , 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferable, and the following structure is more preferable,

It is preferable that Z ^L1 and Z ^L2 be a single bond when the response speed is important.

The number of halogen atoms in the molecule is preferably 0 or 1.

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

(Wherein, R ^L1 and R ^L2 each independently represent the same meaning as R ^L1 and R ^L2 in general formula (L).)
R ^L11 and R ^L12 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, and linear alkenyl groups having 2 to 5 carbon atoms. . The compounds represented by General Formula (L-1) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like. The type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.

The lower limit of the preferred content is 1%, 2%, 3%, 5%, 7%, 10%, based on the total weight of the composition of the present invention. %, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%. The upper limit of the preferred content is 95%, 90%, 85%, 80%, 75%, 70%, based on the total weight of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.

When the composition of the present invention is required to keep the viscosity low and have a high response speed, it is preferable that the above lower limit is high and the upper limit is high. Furthermore, when the composition of the present invention needs to have a high Tni and a composition having good temperature stability is required, it is preferable that the above lower limit value is medium and the upper limit value is medium. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable that the above lower limit value is low and the upper limit value is low.

The compound represented by General Formula (L-1) is preferably a compound represented by General Formula (L-1-1).

^{(Wherein, R L11} represents a hydrogen atom or a methyl ^{group, R L2} represents the same meaning as ^{R L2} in Formula (L).)
The compound represented by General Formula (L-1-1) is a compound selected from the group of compounds represented by Formula (L-1-1.11) to Formula (L-1.1.13) It is preferable that it is a compound represented by the formula (L-1-1.12) or the formula (L-1.1.13), and in particular, it is represented by the formula (L-1.1.13) It is preferable that it is a compound.

In addition, the compound represented by General Formula (L-1-1) is a compound selected from the group of compounds represented by Formula (L-1-1.21) to Formula (L-1-1.24) The compound is preferably a compound represented by the formula (L-1-1.22) to the formula (L-1-1.24). In particular, a compound represented by the formula (L-1-1.22) is preferable because it particularly improves the response speed of the composition of the present invention. Further, when Tni higher than the response speed is to be determined, it is preferable to use a compound represented by the formula (L-1-1.23) or the formula (L-1-1.24).

In addition, the compound represented by General Formula (L-1-1) is a compound selected from the group of compounds represented by Formula (L-1-1.31) and Formula (L-1-1.41) Is preferred.

In addition, the compound represented by General Formula (L-1) is preferably a compound represented by General Formula (L-1-2).

(Wherein, R ¹²¹ and R ¹²² each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
The compound represented by General Formula (L-1-2) is a compound selected from the group of compounds represented by Formula (L-1-2.1) to Formula (L-1-2.12) And is preferably a compound represented by formula (L-1-2.1), formula (L-1-2.3) or formula (L-1-2.4). In particular, a compound represented by the formula (L-1-2.1) is preferable because it particularly improves the response speed of the composition of the present invention. In addition, when Tni higher than the response speed is to be determined, the formula (L-1-2.3), the formula (L-1-2.4), the formula (L-1-2.11), and the formula (L-) are used. It is preferable to use a compound represented by 1-2.12). Sum of compounds represented by the formula (L-1-2.3), the formula (L-1-2.4), the formula (L-1-2.11) and the formula (L-1-2.12) It is not preferable to make the content of 20% or more to improve the solubility at low temperature.

In addition, the compound represented by General Formula (L-1) is preferably a compound selected from the group of compounds represented by General Formula (L-1-3) and / or (L-1-4) .

( ^Wherein , each of R ⁱⁱ³¹ and R ⁱⁱ⁴¹ independently represents the same meaning as R ⁱⁱ² in formula (L)).
The compound represented by General Formula (L) is preferably a compound represented by General Formula (L-2) to General Formula (L-11). The liquid crystal composition of the present invention contains one or more compounds represented by General Formula (L-2) to General Formula (L-11) as the compound represented by General Formula (L) Is preferred.

(Wherein, R ^L31 and R ^{L32 each} represent an alkyl group having 1 to 5 carbon atoms or an alkenyl group containing 2 to 5 carbon atoms, R ^L32 represents an alkyl group having 1 to 5 carbon atoms, or one carbon atom) 5 represents an alkoxyl group, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms)
The compound represented by General Formula (L) is a compound selected from General Formula (L-4), General Formula (L-6), General Formula (L-7) and General Formula (L-8) And more preferably a compound selected from general formula (L-6), general formula (L-7) and general formula (L-8), and general formula (L-7) and general formula (L-). The compound is more preferably a compound selected from 8), and is also preferably a compound selected from General Formula (L-6) and General Formula (L-8). More specifically, when a large Δn is required, the compound is preferably a compound selected from General Formula (L-6), General Formula (L-8), and General Formula (L-11).
In the compounds represented by general formula (L-4), general formula (L-7) and general formula (L-8), R ^L31 is an alkyl group having 1 to 5 carbon atoms or 2 carbon atoms And R ^{L 32} is preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and R ^{L 31} is an alkenyl group having 2 to 5 carbon atoms. More preferably, it is more preferably an alkenyl group having 2 or 3 carbon atoms, and in the compound represented by General Formula (L-6), R ^L31 and R ^L32 each independently have 1 to 5 carbon atoms It is preferable that it is an alkyl group or an alkenyl group having 2 to 5 carbon atoms.

Moreover, as a compound represented by General Formula (L), the compound represented by General Formula (L-12), General Formula (L-13), or General Formula (L-14) is contained 1 type or 2 types or more Is also preferred.

(Expressed in the ^{formula, R L51} and ^{R L52} are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 2 to ^{5 X L51} and X ^{L 52} each independently represents a fluorine atom or a hydrogen atom, and any one of X ^L ⁵¹ and X ^{L 52} is a fluorine atom, and the other is a hydrogen atom.
Moreover, as a compound represented by general formula (L), you may contain 1 type, or 2 or more types of compounds represented by general formula (L-16. 1) to general formula (L-16. 3). .

In addition, as a compound represented by General Formula (L), one or two or more compounds represented by General Formula (N-001) may be contained.

(Wherein, R ^N1 and R ^N2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or 2 to 8 carbon atoms L ¹ and L ² each independently represent a hydrogen atom, a fluorine atom, CH ₃ or CF ₃ , provided that both L ¹ and L ² represent a fluorine atom.
Preferably, R ^N1 and R ^N2 represent an alkyl group having 1 to 5 carbon atoms.

The liquid crystal composition of the present invention preferably has a positive dielectric anisotropy (Δε) at 25 ° C., and the dielectric anisotropy (Δε) at 25 ° C. is 1.5 to 20.0. Is preferable, 1.5 to 18.0 is more preferable, 1.5 to 15.0 is more preferable, 1.5 to 11 is further preferable, and 1.5 to 8 is particularly preferable. The liquid crystal composition having a positive value) preferably contains a compound represented by General Formula (J) and a compound represented by General Formula (L). More specifically, it is preferable to contain the compound represented by Formula (M) and the compound represented by Formula (L-1), and Formula (M-1) and / or Formula (M) It is preferable to contain the compound represented by -2) and the compound represented by the general formula (L-1-1).

The liquid crystal composition of the present invention is a total of the compound represented by the general formula (i) and / or the general formula (ii), the compound represented by the general formula (J) and the compound represented by the general formula (L) In the composition, the lower limit thereof is preferably 5% or more, preferably 80% or more, more preferably 85% or more, and preferably 88% or more. % Is preferable, 92% or more is preferable, 95% or more is preferable, 97% or more is preferable, 98% or more is preferable, and 99% or more is preferable. Is preferable, and it is preferable not to contain substantially other compounds. Further, the upper limit thereof is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not. Substantially means that the compound which is unintentionally contained, such as an impurity produced unavoidable at the time of manufacture, is removed.

The liquid crystal composition of the present invention is a total of the compound represented by the general formula (i) and / or the general formula (ii), the compound represented by the general formula (M) and the compound represented by the general formula (L) In the composition, the lower limit thereof is preferably 5% or more, preferably 80% or more, more preferably 85% or more, and preferably 88% or more. % Is preferable, 92% or more is preferable, 95% or more is preferable, 97% or more is preferable, 98% or more is preferable, and 99% or more is preferable. Is preferable, and it is preferable not to contain substantially other compounds. Further, the upper limit thereof is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not.

The liquid crystal composition of the present invention comprises the compound represented by the general formula (i) and / or the general formula (ii), the compound represented by the general formula (J) and the compound represented by the general formula (L-1) The lower limit of the total content of the composition is preferably 5% or more, preferably 10% or more, preferably 13% or more, and preferably 15% or more. , 18% or more, preferably 20% or more, preferably 23% or more, preferably 25% or more, preferably 28% or more, 30% or more The content is preferably 33% or more, preferably 35% or more, preferably 38% or more, and preferably 40% or more. The upper limit thereof is preferably 95% or less, preferably 90% or less, preferably 88% or less, preferably 85% or less, and preferably 83% or less. 80% or less is preferable, 78% or less is preferable, 75% or less is preferable, 73% or less is preferable, 70% or less is preferable, and 68% or less Is preferably contained, preferably 65% or less, preferably 63% or less, preferably 60% or less, preferably 55% or less, and preferably 50% or less, It is preferable to contain 40% or less.

The liquid crystal composition of the present invention preferably has a negative dielectric anisotropy (Δε) at 25 ° C., and the dielectric anisotropy (Δε) at 25 ° C. is −2.0 to −8.0. Is preferably -2.0 to -6.0, more preferably -2.0 to -5.0, and particularly preferably -2.5 to -4.0.

The liquid crystal composition having a negative dielectric anisotropy (Δε) is a compound represented by the general formula (N-1) to the general formula (N-3) and a compound represented by the general formula (L) It is preferable to contain More specifically, it is preferable to contain the compound represented by the general formula (N-1) and the compound represented by the general formula (L-1), and the compound represented by the general formula (N-1) And the compound represented by formula (L-1-1) is preferable.

The liquid crystal composition of the present invention is a compound represented by the general formula (i) and / or the general formula (ii), a compound represented by the general formula (N-1) to the general formula (N-3) and a general formula The lower limit of the total content of the compound represented by (L) is preferably 5% or more, preferably 80% or more, and preferably 85% or more. The content is preferably 88% or more, preferably 90% or more, preferably 92% or more, preferably 95% or more, preferably 97% or more, and 98% or more It is preferable to contain at least 99%, and it is preferable to contain substantially no other compound. Further, the upper limit thereof is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not.

The liquid crystal composition of the present invention comprises the compound represented by the general formula (i) and / or the general formula (ii), the compound represented by the general formula (N-1) and the compound represented by the general formula (L) The lower limit of the total content of the composition is preferably 5% or more, preferably 80% or more, preferably 85% or more, and preferably 88% or more. 90% or more is preferable, 92% or more is preferable, 95% or more is preferable, 97% or more is preferable, 98% or more is preferable, and 99% or more is preferable. It is preferable to be substantially free of other compounds. Further, the upper limit thereof is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains other compounds. Preferably not.

The liquid crystal composition of the present invention has a refractive index anisotropy (Δn) at 25 ° C. of 0.08 to 0.14, preferably 0.09 to 0.13, and more preferably 0.09 to 0.12. Particularly preferred. More specifically, in the case of a thin cell gap, it is preferably 0.10 to 0.13, and in the case of a thick cell gap, it is preferably 0.08 to 0.10.

The liquid crystal composition of the present invention has a viscosity (η) at 25 ° C. of 10 to 50 mPa · s, more preferably 10 to 40 mPa · s, particularly preferably 10 to 35 mPa · s.

The liquid crystal composition of the present invention has a rotational viscosity (γ ₁ ) at 25 ° C. of 60 to 130 mPa · s, more preferably 60 to 110 mPa · s, and particularly preferably 60 to 100 mPa · s. .

The liquid crystal composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T _ni ) of 60 ° C. to 120 ° C., preferably 70 ° C. to 100 ° C., particularly preferably 70 ° C. to 85 ° C.

The liquid crystal composition of the present invention may contain, in addition to the above-mentioned compounds, ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, polymerizable monomers, and the like.

For example, the liquid crystal composition of the present invention may contain a liquid crystal compound having a dielectric anisotropy (Δε) of +2.0 to +50.0 at 25 ° C. as an ordinary nematic liquid crystal or a smectic liquid crystal, The content is 0% to 50% by mass, preferably 1% to 30% by mass, preferably 3% to 30% by mass, and 5% to 20% by mass. Is preferred.

For example, the liquid crystal composition may contain 0.01 to 2% by mass of a polymerizable compound such as a biphenyl derivative or a terphenyl derivative as a polymerizable monomer.

As the polymerizable monomer, one or two types of monofunctional polymerizable compounds having one reactive group and polyfunctional polymerizable compounds having two or more reactive groups such as difunctional or trifunctional compounds You may contain more than. The polymerizable compound having a reactive group may or may not contain a mesogenic site.

In the polymerizable compound having a reactive group, the reactive group is preferably a substituent having polymerizability by light.

Among polymerizable compounds having a reactive group, specifically, a polymerizable compound having a monofunctional reactive group is represented by the following general formula (VI)

(Wherein, X ³ represents a hydrogen atom or a methyl group, and Sp ³ is a single bond, an alkylene group having 1 to 8 carbon atoms, or -O- (CH ₂ ) _t- (wherein t is 2 to Represents an integer of 7 and an oxygen atom is bonded to an aromatic ring), and V represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic group having 5 to 30 carbon atoms. The alkylene group in the polyvalent alkylene group may be substituted by an oxygen atom within the range where the oxygen atom is not adjacent, although an alkyl group having 5 to 20 carbon atoms (the alkylene group in the group is an oxygen atom) May be substituted by an oxygen atom within the range not adjacent to each other) or may be substituted by a cyclic substituent, and W represents a hydrogen atom, a halogen atom or an alkylene group having 1 to 8 carbon atoms. The polymerizable compounds represented are preferred.

In the above general formula (VI), X ³ represents a hydrogen atom or a methyl group, but a hydrogen atom is preferable when the reaction rate is important, and a methyl group is important when the reduction of the reaction residual amount is important. preferable.

In the above general formula (VI), Sp ³ represents a single bond, an alkylene group having 1 to 8 carbon atoms, or -O- (CH ₂ ) _t- (wherein _t represents an integer of 2 to 7 and an oxygen atom Represents an aromatic ring), but the carbon chain is preferably not so long, preferably a single bond or an alkylene group having 1 to 5 carbon atoms, and preferably a single bond or 1 to 3 carbon atoms. An alkylene group is more preferred. In addition, when Sp ³ represents -O- (CH ₂ ) _t- , t is preferably 1 to 5, and more preferably 1 to 3.

In the above general formula (VI), V represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic substituent having 5 to 30 carbon atoms, and an alkylene group in the polyvalent alkylene group May be substituted by an oxygen atom within the range where the oxygen atom is not adjacent, and the alkyl group having 5 to 20 carbon atoms (the alkylene group in the group may be substituted by an oxygen atom within the range where the oxygen atom is not adjacent Or cyclic substituent, and preferably substituted by two or more cyclic substituents.

More specifically, the polymerizable compound represented by the general formula (VI) is represented by the general formula (X1a)

(Wherein, A ¹ represents a hydrogen atom or a methyl group,
A ² represents a single bond or an alkylene group having 1 to 8 carbon atoms (one or more methylene groups in the alkylene group each independently represent an oxygen atom, as the oxygen atom is not directly bonded to each other) It may be substituted by -CO-, -COO- or -OCO-, and one or more hydrogen atoms in the alkylene group are each independently substituted with a fluorine atom, a methyl group or an ethyl group May be represented by
Each A ³ and A ⁶ are independently a hydrogen atom, one, or two or more methylene groups in the alkyl group (the alkyl group of a halogen atom or a carbon atom number of 1 to 10, the oxygen atoms are not directly bonded to each other And each may be independently substituted with an oxygen atom, -CO-, -COO- or -OCO-, and one or more hydrogen atoms in the alkyl group are each independently a halogen Optionally substituted with an alkyl group or an alkyl group having 1 to 17 carbon atoms.
A ⁴ and A ⁷ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms (in which one or more methylene groups in the alkyl group, oxygen atoms do not bond directly to each other) And each may be independently substituted with an oxygen atom, -CO-, -COO- or -OCO-, and one or more hydrogen atoms in the alkyl group are each independently a halogen Optionally substituted with an alkyl group or an alkyl group having 1 to 9 carbon atoms,
p represents 1 to 10,
B ¹ , B ² and B ³ each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms (one or more methylene groups in the alkyl group are And oxygen atoms which may not be directly bonded to each other may be each independently substituted with an oxygen atom, -CO-, -COO- or -OCO-, and one or more in the alkyl group And each hydrogen atom may be independently substituted with a halogen atom or a trialkoxysilyl group having 3 to 6 carbon atoms.

Specifically, the polymerizable compound represented by the general formula (VI) is represented by the general formula (X1b)

(Wherein, A ⁸ represents a hydrogen atom or a methyl group,
Six-membered rings T ¹ , T ² and T ³ are each independently

Represents any of (where q represents an integer of 1 to 4), and
q represents 0 or 1;
Y ¹ and Y ² are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O—, —OCH ₂ —, —COO—, —OCO—, —C≡C—, —CH = CH— _{_{_{_{, -CF = CF -, - (}}}} CH 2) 4 -, - CH 2 CH 2 CH 2 O -, - OCH 2 CH 2 CH 2 -, - CH 2 = CHCH 2 CH 2 - or _-CH 2 _CH 2 CH Represents = CH-,
Y ³ represents a single bond, -COO- or -OCO-,
B ⁸ is a hydrocarbon group having 1 to 18 carbon atoms. Also included are compounds represented by).

Furthermore, specifically, the polymerizable compound represented by the general formula (VI) is a compound represented by the general formula (X1c)

(Wherein, R ⁷⁰ represents a hydrogen atom or a methyl group, and R ⁷¹ represents a hydrocarbon group having a condensed ring).

Further, among polymerizable compounds having a reactive group, a polymerizable compound having a multifunctional reactive group is represented by the following general formula (VII)

(Wherein, X ¹ and X ² each independently represent a hydrogen atom or a methyl group, and Sp ¹ and Sp ² each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH ₂ ) _s- (wherein, s represents an integer of 2 to 7, and an oxygen atom is bonded to an aromatic ring), and U represents a linear or branched multi chain having 2 to 20 carbon atoms And an alkylene group in the polyvalent alkylene group may be substituted by an oxygen atom within the range in which the oxygen atom is not adjacent, and has 5 carbon atoms. ～ 20 alkyl group (the alkylene group in the group may be substituted by an oxygen atom as long as the oxygen atom is not adjacent) or may be substituted by a cyclic substituent, and k is an integer of 1 to 5 The polymerizable compound represented by is preferable. .
In the above general formula (VII), X ¹ and X ² each independently represent a hydrogen atom or a methyl group, but when importance is placed on the reaction rate, a hydrogen atom is preferable, and it is emphasized to reduce the residual amount of reaction If it is a methyl group is preferred.

In the above general formula (VII), Sp ¹ and Sp ² are each independently a single bond, an alkylene group having 1 to 8 carbon atoms, or -O- (CH ₂ ) _s- (wherein s is 2 to 7) And the oxygen atom is to be bonded to an aromatic ring), but the carbon chain is preferably not so long, preferably a single bond or an alkylene group having 1 to 5 carbon atoms, a single bond or An alkylene group having 1 to 3 carbon atoms is more preferable. Further, when Sp ¹ and Sp ^{2 each} represent -O- (CH ₂ ) _s- , s is preferably 1 to 5, more preferably 1 to 3, and at least one of Sp ¹ and Sp ² is a single bond. It is more preferable that any of them is a single bond.

In the above general formula (VII), U represents a linear or branched polyvalent alkylene group having 2 to 20 carbon atoms or a polyvalent cyclic substituent having 5 to 30 carbon atoms, and an alkylene group in the polyvalent alkylene group May be substituted by an oxygen atom within the range where the oxygen atom is not adjacent, and the alkyl group having 5 to 20 carbon atoms (the alkylene group in the group may be substituted by an oxygen atom within the range where the oxygen atom is not adjacent ), Which may be substituted by a cyclic substituent, and preferably substituted by two or more cyclic substituents.

In the above general formula (VII), specifically, U preferably represents the following formulas (VII-1) to (VII-5), and the formula (VII-1) to the formula (VII-3) It is more preferable to represent, and it is particularly preferable to represent the formula (VII-1).

(Wherein both ends are bound to Sp ¹ or Sp ² )
When U has a ring structure, at least one of Sp ¹ and Sp ² preferably represents a single bond, and both are preferably single bonds.

In the above general formula (VII), k represents an integer of 1 to 5, preferably a bifunctional compound in which k is 1 or a trifunctional compound in which k is 2 and more preferably a bifunctional compound. .

More specifically, the general formula (P)

It is preferable to contain 1 or 2 types or more of polymerizable compounds represented by these.

In formula (P), X ²⁰¹ and X ²⁰² each independently represent a hydrogen atom, a methyl group or a —CF ₃ group. X ²⁰¹ and X ²⁰² are diacrylates derivatives each a hydrogen atom, dimethacrylate derivatives are preferred both a methyl group, one compound other is a hydrogen atom is a methyl group are also preferred. Although a preferable compound can be used depending on the application, in the PSA display element, the polymerizable compound represented by the general formula (P) preferably has at least one methacrylate derivative, and also preferably has two.

In Formula (P), Sp ²⁰¹ and Sp ²⁰² each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or -O- (CH ₂ ) _s- (wherein s is 2 to 7) And an oxygen atom is to be bonded to a ring. It is preferable that at least one of Sp ²⁰¹ and Sp ²⁰² is a single bond in a liquid crystal display element of PSA type, and both are single bonds, or one is a single bond and the other is an alkylene having 1 to 8 carbon atoms. It is preferably a group or -O- (CH ₂ ) _s- , in which case an alkylene group having 1 to 4 carbon atoms is preferable, and s is preferably 1 to 4.

In formula (P), each of M ²⁰¹ , M ²⁰² and M ²⁰³ independently represents a trans-1,4-cyclohexylene group (one or two or more non-adjacent -CH ₂ -in the group are -O- or -S- may be substituted), 1,4-phenylene group (one or two or more non-adjacent -CH = in the group may be substituted by -N = Good), 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene- 2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, wherein each hydrogen atom in the group is independently a fluorine atom, a -CF ₃ group, the number of carbon atoms 1 to 10 alkyl group, 1 to 1 carbon atom It may be substituted by an alkoxyl group of 0 or any of formulas (R-1) to (R-15).

In general formula (P), Z ²⁰¹ and Z ²⁰² are each independently -OCH _2- , -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -,- _{_{_{_{CH 2 CH 2 -, - CF}}}} 2 CF 2 -, - CH = CH-COO -, - CH = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -COO-CH _2- , -OCO-CH _2- , -CH ₂ -COO -, -CH ₂ -OCO-, -CY ¹ = CY ^2- (wherein, Y ¹ and Y ² each independently represent a fluorine atom or a hydrogen atom), -C≡C- or a single bond But represents -COO-, -OCO-, -CH = CH-COO-,- H = CH-OCO -, - COO-CH = CH -, - OCO-CH = CH -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO-, -CH ₂ CH ₂ -OCO-, -C≡C- or a single bond is preferable, and -COO-, -OCO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH _{_{-, - OCO-CH = CH}} -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- or a single bond is more preferable.

In the general formula (P), n ²⁰¹ represents 0, 1 or 2, preferably 0 or 1. However, when there are a plurality of M ²⁰² and Z ²⁰² , they may be different or the same.

The polymerizable compound represented by formula (P) may contain at least one kind, preferably one to five, and more preferably one to three.
The content of the general formula (P) is preferably 0.01 to 2.00% by mass, more preferably 0.05 to 1.00% by mass, and 0.10 to 0.50% by mass. Being particularly preferred.

More specifically, when n ²⁰¹ is 0 in General Formula (P), the ring structure between Sp ²⁰¹ and Sp ²⁰² is preferably Formula (XXa-1) to Formula (XXa-5), Formula (XXa-1) to formula (XXa-3) is more preferable, and formula (XXa-1) or formula (XXa-2) is particularly preferable. However, both ends of the formula are assumed to be coupled to Sp ²⁰¹ or Sp ²⁰² .

The polymerizable compound represented by the general formula (P) containing these skeletons is suitable for the liquid crystal display element of PSA type after the polymerization is regulated, and a good alignment state is obtained, thereby suppressing display unevenness. There is an effect that occurs or does not occur at all.

From the above, as the polymerizable monomer, compounds represented by Formula (XX-1) to Formula (XX-10) are preferable, and Formula (XX-1) to Formula (XX-4) are more preferable.

In the general formulas (XX-1) to (XX-10), Sp ^xx is an alkylene group having 1 to 8 carbon atoms or -O- (CH ₂ ) _s- (wherein s is an integer of 2 to 7) And the oxygen atom is taken to be attached to the ring).

The hydrogen atom in the 1,4-phenylene group in the general formula (XX-1) to the general formula (XX-1) is further represented by -F, -Cl, -CF ₃ , -CH ₃ and the formula (R-1) And may be substituted by any of formulas (R-15).

When n ²⁰¹ is 1 in General Formula (P), for example, polymerizable compounds such as Formula (P31) to Formula (P48) are preferable.

Hydrogen atoms of the 1,4-phenylene group and in the naphthalene radical of the formula (P48) from the formula (P31) _{further, -F, -Cl, -CF 3,} -CH 3, wherein the formula (R-1) It may be substituted by any of (R-15).

When n ²⁰¹ is 1 in General Formula (P) and has a plurality of Formula (R-1) or Formula (R-2), for example, polymerizable compounds such as Formula (P301) to Formula (P316) are preferable.

The hydrogen atoms in the 1,4-phenylene group and the naphthalene group in formulas (P301) to (P316) may be further substituted by -F, -Cl, -CF ₃ or -CH ₃ .

As the polymerizable compound represented by the general formula (P), for example, polymerizable compounds such as formulas (Ia-1) to (Ia-31) are also preferable.

In addition, the liquid crystal composition of the present invention may further contain a hindered amine light stabilizer and / or an antioxidant which does not have an unpaired electron. The antioxidant is preferably a hindered phenol represented by general formula (H-1) to general formula (H-4).

In the general formula (H-1) to the general formula (H-4), R ^H1 represents an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or An alkenyloxy group having 2 to 10 carbon atoms is represented, but one —CH ₂ — or non-adjacent two or more —CH ₂ — present in the group are each independently —O— or —S— And one or more hydrogen atoms present in the group may be independently substituted with a fluorine atom or a chlorine atom. More specifically, it is an alkyl group having 2 to 7 carbon atoms, an alkoxyl group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms. More preferably, it is an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.
In the general formula (H-4), M ^H4 is an alkylene group having 1 to 15 carbon atoms (one or more -CH _2- in the alkylene group is such that an oxygen atom is not directly adjacent to- It may be substituted by O-, -CO-, -COO-, -OCO-), -OCH _2- , -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-,- OCF _2- , -CF ₂ CF _2- , -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-,- C≡C—, single bond, 1,4-phenylene group (optional hydrogen atom in 1,4-phenylene group may be substituted by fluorine atom) or trans-1,4-cyclohexylene group Is preferably an alkylene group having 1 to 14 carbon atoms, In view of viscosity, it is preferable that the number of carbon atoms is large, but in view of viscosity, it is preferable that the number of carbon atoms is not too large, so 2 to 12 carbon atoms are more preferable, and 3 to 10 carbon atoms are more preferable. The carbon number is preferably 4 to 10, more preferably 5 to 10 carbon atoms, and still more preferably 6 to 10 carbon atoms.
In General Formula (H-1) to General Formula (H-4), one or more non-adjacent two or more —CH = in the 1,4-phenylene group may be substituted by —N =. The hydrogen atoms in the 1,4-phenylene group may be each independently substituted with a fluorine atom or a chlorine atom.
In the general formula (H-1) to the general formula (H-4), one or more non-adjacent two or more -CH ₂ -in the 1,4-cyclohexylene group is substituted by -O- or -S- It may be done. The hydrogen atoms in the 1,4-cyclohexylene group may be each independently substituted with a fluorine atom or a chlorine atom.
More specifically, for example, formulas (H-11) to (H-15) may be mentioned.

The liquid crystal composition of the present invention may contain 1 mass ppm or more of an antioxidant, but 10 mass ppm or more is preferable, 20 mass ppm or more is preferable, and 50 mass ppm or more is preferable. Although the upper limit of content of antioxidant is 10000 mass ppm, 1000 mass ppm is preferable, 500 mass ppm is preferable, and 100 mass ppm is preferable.

The liquid crystal display device using the liquid crystal composition of the present invention has no display defects or is suppressed, has a high response speed with excellent display quality, and in particular, for example, a TN type liquid crystal display device driven by active matrix. The present invention can be applied to OCB type, VA type, VA-IPS type, PSVA type, PSA type, FFS type, IPS type or ECB type. The PSVA type and the PSA type are substantially equivalent.

Furthermore, the liquid crystal composition of the present invention containing a polymerizable compound is a polymer-stabilized VA type produced by polymerizing the polymerizable compound contained in the liquid crystal composition under application of voltage or without application of voltage. It is possible to provide a liquid crystal display element such as PSA type, TN type, OCB type, ECB type, IPS type, FFS type or VA-IPS type.

The present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. Moreover, "%" in the composition of the following example and a comparative example means "mass%."
The following abbreviations are used for the description of the compounds in the examples.
(Side chain)
-N -C _n H _{2n + 1} linear carbon number n alkyl group n-C _n H _{2n + 1-} linear carbon number n carbon group -On-OC _n H _{2n + 1} linear carbon alkoxy number n group nO- C _n H _2n + 1 O- straight chain alkoxy group with carbon number n -V -CH = CH ₂
V-CH ₂ = CH-
-V1 -CH = CH-CH ₃
1V- CH ₃ -CH = CH-
-2V -CH ₂ -CH ₂ -CH = CH ₂
_{_{V2- CH 2 = CH-CH 2}} -CH 2 -
-2V 1 -CH ₂ -CH ₂ -CH = CH-CH ₃
_{_{1V2- CH 3 -CH = CH-CH}} 2 -CH 2 -
(Linking group)
-CFFO- -CF ₂ -O-
-OCFF--O-CF _2-
-1O- -CH ₂ -O-
-O1- -O-CH _2-
-COO- -COO-
-OCO- -OCO-
(Ring structure)

In the examples, the compounds represented below were used as additives as hindered amine light stabilizers having one or more unpaired electrons in the molecule.

Moreover, the comparative example used the compound represented below as an additive.

The compound A-1 was obtained by synthesizing the compound B-1 by light irradiation. The compounds A-2 to A-9 were obtained by synthesizing the compounds B-2 to B-5 by light irradiation.

The characteristics measured in the examples are as follows.

Specific resistance value: The specific resistance value of 1.5 g of liquid crystal was measured using Kawaguchi Electric Co., Ltd. MMAII.

Electron spin resonance: Raw material and liquid crystal radical amounts were measured using a Bruker E 580.

Synthesis of Hals Radical: Halcy was diluted in a solution by a merry-go-round type light irradiator and light was irradiated. The obtained radical compound was quantified by GC and GC-MS.

VHR (UV): The evaluation cell in which the sample is introduced is annealed at 100 ° C. for 2 hours, and the voltage holding ratio (1 V, 5 Hz, 60 ° C.) after irradiation of UV 3 (J) with a high pressure mercury lamp. However, the illuminance was 100 mW / cm ^{2 at} 365 nm. The cell thickness of the test panel is 3.5 μm, and the alignment film is AL16301 (film thickness 80 nm).

(Examples 1 to 4 and Comparative Examples 1 to 5)
The composition (LC-A) shown below was prepared.

The following liquid crystal compositions of LC-A were prepared, and their physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-1), (A-2), (B-1) and (B-2) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-A. It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 2 to 5 and Examples 1 to 4, by containing at least one of the compounds represented by Formulas (A-1) and (A-2), a high specific resistance value can be obtained. I understand. Further, it was confirmed that Examples 1 to 4 have VHR (UV) higher than Comparative Examples 1 to 5. Moreover, it confirmed that there was no display nonuniformity. Incidentally, T _ni, [Delta] n, [Delta] [epsilon] and gamma ₁ value of the liquid crystal compositions used in Examples 1-4 was the same as the value of the liquid crystal composition LC-A.

(Examples 5 to 8, Comparative Examples 6 to 10)
The composition (LC-B) shown below was prepared.

The following LC-B liquid crystal composition was prepared, and its physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-3), (A-5), (B-3) and (B-5) are represented by the following formulas based on 100 parts by mass of the liquid crystal composition LC-B: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 7 to 10 and Examples 5 to 8, high specific resistance can be obtained by containing at least one of the compounds represented by Formulas (A-3) and (A-5). I understand. Further, it was confirmed that Examples 5 to 8 have VHR (UV) higher than Comparative Examples 6 to 10. Moreover, it confirmed that there was no display nonuniformity. The values of T _ni , Δn, Δε and γ ₁ of the liquid crystal compositions used in Examples 5 to 8 were the same as the values of the liquid crystal composition LC-B.
(Examples 9 to 12 and Comparative Examples 11 to 15)
The composition (LC-C) shown below was prepared.

The following LC-C liquid crystal composition was prepared, and its physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-1), (A-2), (B-1) and (B-2) with respect to 100 parts by mass of the liquid crystal composition LC-C are as follows: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

By containing at least any one of the compounds represented by formulas (A-1) and (A-2) from Comparative Examples 12 to 15 and Examples 9 to 12, high specific resistance can be obtained. I understand. Moreover, it was confirmed that Examples 9 to 12 have VHR (UV) higher than Comparative Examples 11 to 15. Moreover, it confirmed that there was no display nonuniformity. The values of T _ni , Δn, Δε and γ ₁ of the liquid crystal compositions used in Examples 9 to 12 were the same as the values of the liquid crystal composition LC-C.

(Examples 13 to 16, Comparative Examples 16 to 20)
The composition (LC-D) shown below was prepared.

The following LC-D liquid crystal compositions were prepared, and their physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-3), (A-4), (B-3) and (B-4) are represented by the following formulas based on 100 parts by mass of the liquid crystal composition LC-D: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 17 to 20 and Examples 13 to 16, by containing at least one of the compounds represented by Formulas (A-3) and (A-4), a high specific resistance value can be obtained. I understand. Further, it was confirmed that Examples 13 to 16 have VHR (UV) higher than Comparative Examples 16 to 20. Moreover, it confirmed that there was no display nonuniformity. The values of T _ni , Δn, Δε and γ ₁ of the liquid crystal compositions used in Examples 13 to 16 were the same as the values of the liquid crystal composition LC-D.

(Examples 17 to 20, Comparative Examples 21 to 25)
The composition (LC-E) shown below was prepared.

The following LC-E liquid crystal composition was prepared, and its physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-1), (A-6), (B-1) and (B-6) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-E: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

By containing at least one of the compounds represented by formulas (A-1) and (A-6) from Comparative Examples 22 to 25 and Examples 17 to 20, a high specific resistance value can be obtained. I understand. Further, it was confirmed that Examples 17 to 20 have VHR (UV) higher than Comparative Examples 21 to 25. Moreover, it confirmed that there was no display nonuniformity. Incidentally, _{T ni,} [Delta] n, [Delta] [epsilon] and gamma ₁ value of the liquid crystal composition used in Examples 17-20 was the same as the value of the liquid crystal composition LC-E.

(Examples 21 to 26, Comparative Examples 24 to 26)
The following composition (LC-F) was prepared.

The following liquid crystal compositions of LC-F were prepared, and their physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-2), (A-8), (A-9) and (B-2) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-F: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

From Comparative Examples 25 to 26 and Examples 21 to 26, the content is higher by containing at least one of the compounds represented by Formula (A-2), Formula (A-8), and (A-9). It can be seen that a specific resistance value can be obtained. Moreover, it was confirmed that Examples 21 to 26 have VHR (UV) higher than Comparative Examples 24 to 26. Moreover, it confirmed that there was no display nonuniformity. Incidentally, _{T ni,} [Delta] n, [Delta] [epsilon] and gamma ₁ value of the liquid crystal composition used in Example 21-24 were the same as the value of the liquid crystal composition LC-F.

(Examples 27 to 31, Comparative examples 27 to 30)
The following composition (LC-I) was prepared.

The following LC-I liquid crystal compositions were prepared, and their physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-1), (A-2), (B-1) and (B-2) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-I. It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

By containing at least any one of the compounds represented by formulas (A-1) and (A-2) from Comparative Examples 28 to 31 and Examples 27 to 30, high specific resistance values can be obtained. I understand. Moreover, it was confirmed that Examples 27 to 30 have VHR (UV) higher than Comparative Examples 27 to 31. Moreover, it confirmed that there was no display nonuniformity. Incidentally, _{T ni,} [Delta] n, [Delta] [epsilon] and gamma ₁ value of the liquid crystal composition used in Example 27-30 were the same as the value of the liquid crystal composition LC-I.

(Examples 31 to 34, Comparative Examples 32 to 36)
The composition (LC-J) shown below was prepared.

The following LC-J liquid crystal composition was prepared, and its physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-4), (A-5), (B-4) and (B-5) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-J: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 33 to 36 and Examples 31 to 34, a high specific resistance value can be obtained by containing at least one of the compounds represented by Formulas (A-1) and (A-2). I understand. Further, it was confirmed that Examples 31 to 34 have VHR (UV) higher than Comparative Examples 32 to 36. Moreover, it confirmed that there was no display nonuniformity. Incidentally, _{T ni,} [Delta] n, [Delta] [epsilon] and gamma ₁ value of the liquid crystal composition used in Examples 31 to 34 were the same as the value of the liquid crystal composition LC-J.

(Examples 35 to 35, Comparative Examples 37 to 45)
The composition (LC-K) shown below was prepared.

The following LC-K liquid crystal composition was prepared, and its physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-1), (A-2), (B-1) and (B-2) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-K: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 38 to 41 and Examples 35 to 38, by containing at least one of the compounds represented by Formulas (A-1) and (A-2), a high specific resistance value can be obtained. I understand. Moreover, it was confirmed that Examples 35 to 38 have VHR (UV) higher than Comparative Examples 37 to 41. Moreover, it confirmed that there was no display nonuniformity. The values of T _ni , Δn, Δε and γ ₁ of the liquid crystal compositions used in Examples 35 to 38 were the same as the values of the liquid crystal composition LC-K.

(Examples 39 to 44, Comparative Examples 42 to 44)
The composition (LC-L) shown below was prepared.

The following LC-L liquid crystal compositions were prepared, and their physical property values were measured. The composition of the liquid crystal composition and the results of the physical properties were as shown in the table.

The compounds represented by the above formulas (A-2), (A-8), (A-1) and (B-2) are expressed by the following formula based on 100 parts by mass of the liquid crystal composition LC-L: It added in the ratio shown in the table, and measured the specific resistance value and VHR. The results are shown below.

According to Comparative Examples 43 to 44 and Examples 39 to 44, a high specific resistance value can be obtained by containing at least one of the compounds represented by Formulas (A-1) and (A-2). I understand. Further, it was confirmed that Examples 39 to 44 have VHR (UV) higher than Comparative Examples 42 to 44. Moreover, it confirmed that there was no display nonuniformity. The values of T _ni , Δn, Δε and γ ₁ of the liquid crystal compositions used in Examples 39 to 44 were the same as the values of the liquid crystal composition LC-L.

Claims

A liquid crystal composition containing one or more hindered amine light stabilizers having one or more unpaired electrons in the molecule.
The hindered amine light stabilizer has a general formula (i)

(Wherein, R i0 represents a hydrogen atom, a hydroxyl group, -O.-, Or an alkyl group having 1 to 20 carbon atoms, and one or more non-adjacent -CH 2 present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- , -C≡C -, - Si (CH 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl group, in R i0 Or one or more hydrogen atoms may be independently substituted with a fluorine atom, a chlorine atom or a cyano group Bur, represents at least one or more R i0 is -O ·,
R i1 , R i2 , R i3 and R i4 each independently represent an alkyl group having 1 to 12 carbon atoms, and R i1 and R i2 and / or R i3 and R i4 combine with each other to form a ring You may
R i5 , R i6 , R i7 and R i8 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and when R i5 and R i6 and / or R i7 and R i8 represent an alkyl group And R i5 and R i6 and / or R i7 and R i8 may be bonded to each other to form a ring,
n i represents 0 or 1 and
m i represents an integer of 1 to 6, M i represents a monovalent to hexavalent organic group, the valence number of M i is the same number as the number represented by m i , and when there are a plurality of R i 0 , Are the same or different, but at least one or more of R i0 represents -O ·, and R i1 , R i2 , R i3 , R i4 , R i5 , R i6 , R i7 , R i8 When a plurality of n i are present, they may be the same or different. )
Or general formula (ii)

(Wherein, R ii0 represents a hydrogen atom, a hydroxyl group, -O.-, Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent -CH 2 present in the alkyl group -Is each independently -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH- , -C≡C -, - Si (CH 3) 2 -, trans 1,4-cyclohexylene group may be substituted by a 1,4-phenylene group or a naphthalene-2,6-diyl group, in R ii0 Or one or more hydrogen atoms are independently substituted with a fluorine atom, a chlorine atom or a cyano group It may also be, but at least one or more R ii0 represents -O ·,
R ii1 , R ii2 , R ii3 and R ii4 each independently represent an alkyl group having 1 to 12 carbon atoms, and R ii1 and R ii2 and / or R ii3 and R ii4 combine with each other to form a ring You may
R ii5 , R ii6 , R ii7 and R ii8 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and in the case where R ii5 and R ii6 and / or R ii7 and R ii8 represent an alkyl group And said R ii5 and R ii6 and / or R ii7 and R ii8 may be bonded to each other to form a ring,
n ii represents 0 or 1;
m ii represents from 1 4, U ii represents 2 × m ii valent organic group that forms a ring structure, if R ii0 there are a plurality, they may be different even identical, at least one R i0 represents -O ·, if R ii1, R ii2, R ii3 , R ii4, R ii5, R ii6, R ii7, R ii8 and n ii there are a plurality, they may at the same It may be different or different. )
The liquid crystal composition according to claim 1, which is a compound represented by
Furthermore, general formula (II)

(Wherein, R II1 represents an alkyl group having 1 to 10 carbon atoms, and one or two non-adjacent —CH 2 — in the alkyl group are each independently —CH = CH—, — It may be substituted by C≡C-, -O-, -CO-, -COO- or -OCO-,
A II1 and A II2 are each independently (a) 1,4-cyclohexylene group (one —CH 2 — present in this group or two or more non-adjacent —CH 2 — is —O And-(b) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = replaced by -N = May be
(C) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or One —CH = or two or more non-adjacent —CH = present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by —N =. )
And the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z II1 is a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O— , -CH = N-N = CH-, -CH = CH-, -CF = CF- or -C≡C-,
Y II1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent -CH 2 -in the alkyl group are each independently Optionally substituted by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or more hydrogens in the alkyl group The atom may be substituted by a fluorine atom,
Although m II1 represents 1, 2, 3 or 4, when m II1 represents 2, 3 or 4, two or more A II1 and Z II1 may be the same or different. )
The liquid crystal composition according to any one of claims 1 or 2, which contains one or more liquid crystal compounds represented by
The liquid crystal composition according to any one of claims 1 to 3, further comprising one or more polymerizable compounds.
The liquid crystal composition according to any one of claims 1 to 4, wherein the total content of the hindered amine light stabilizer is 0.001% by mass to 5% by mass in the liquid crystal composition.
The liquid crystal composition according to any one of claims 3 to 5, wherein the total content of the compound represented by formula (II) is 10% by mass or more in the liquid crystal composition.
Nematic phase-isotropic liquid having refractive index anisotropy (Δn) at 25 ° C. in the range of 0.08 to 0.14 and rotational viscosity (γ1) at 25 ° C. in the range of 60 to 130 mPa · s The liquid crystal composition according to any one of claims 1 to 6, wherein the phase transition temperature (T ni ) is in the range of 60 ° C to 120 ° C.
A display device using the composition according to any one of claims 1 to 7.