CN111183206A

CN111183206A - Alignment aid, liquid crystal composition and liquid crystal display element

Info

Publication number: CN111183206A
Application number: CN201880051838.XA
Authority: CN
Inventors: 木村正臣; 须藤豪; 井之上雄一; 幡野直美; 林正直; 间宫纯一; 清水健太
Original assignee: DIC Corp
Current assignee: DIC Corp
Priority date: 2017-09-08
Filing date: 2018-08-23
Publication date: 2020-05-19
Anticipated expiration: 2038-08-23
Also published as: KR20200041880A; TW201920629A; JP6690782B2; JPWO2019049673A1; CN111183206B; WO2019049673A1

Abstract

The invention provides an alignment aid which can ensure storage stability when added to a liquid crystal composition and enables liquid crystal molecules to spontaneously vertically align even if a PI layer is omitted. The present invention also provides a liquid crystal composition having excellent storage stability and capable of vertical alignment of liquid crystal molecules even if a PI layer is omitted, and a liquid crystal display element using the liquid crystal composition. The alignment assistant of the present invention is disposed between two substrates together with liquid crystal molecules, and aligns the liquid crystal molecules spontaneously. The orientation aid is characterized by containing: a first compound comprising at least one first affinity group having an affinity with respect to the substrate; and a second compound including at least one second affinity group having an affinity for the substrate and having a polarity lower than that of the first affinity group.

Description

Alignment aid, liquid crystal composition and liquid crystal display element

Technical Field

The invention relates to an alignment aid, a liquid crystal composition and a liquid crystal display element.

Background

In a conventional Vertical Alignment (VA) liquid crystal display, a Polyimide (PI) layer functioning as an alignment layer is provided on an electrode in order to induce vertical alignment of liquid crystal molecules when no voltage is applied and to achieve horizontal alignment of the liquid crystal molecules when a voltage is applied. However, since a high cost is required for forming the PI layer, a method for aligning liquid crystal molecules even if the PI layer is omitted has been studied in recent years.

For example, patent document 1 discloses a liquid crystal medium characterized in that: the description is based on a mixture of polar compounds having negative dielectric anisotropy and containing at least one spontaneously orienting additive, and describes that the liquid crystal medium can be suitably used in displays which do not contain an orienting layer. Further, in patent document 1, a specific compound having a hydroxyl group is used as a spontaneous alignment additive.

Documents of the prior art

Patent document

Patent document 1: japanese Kohyo publication 2014-524951

Disclosure of Invention

Problems to be solved by the invention

However, according to the studies of the present inventors, it has been found that when the self-aligning additive described in patent document 1 is used, the orientation constraint force for vertically aligning the liquid crystal molecules is insufficient, and when a liquid crystal display element having no PI layer is produced, alignment unevenness occurs at the end of the liquid crystal display element due to the liquid crystal molecules not exhibiting a predetermined alignment state, and thus improvement is required, and that crystal deposition occurs when a liquid crystal composition containing the self-aligning additive is stored, and there is room for improvement in storage stability.

Accordingly, an object of the present invention is to provide an alignment aid which can ensure storage stability of a liquid crystal composition containing an alignment aid (self-aligning additive) and liquid crystal molecules and can spontaneously vertically align the liquid crystal molecules even if a PI layer is omitted. Another object of the present invention is to provide a liquid crystal composition which has excellent storage stability and can realize a liquid crystal display element of a Polymer Sustained Alignment (PSA) type, a Polymer Sustained Vertical Alignment (PSVA) type, a VA type, or the like even if a PI layer is omitted, and a liquid crystal display element using the liquid crystal composition.

Means for solving the problems

The present invention provides an alignment aid which is disposed between two substrates together with liquid crystal molecules and which aligns the liquid crystal molecules spontaneously, the alignment aid comprising:

a first compound comprising at least one first affinity group having an affinity with respect to the substrate; and

a second compound including at least one second affinity group having an affinity for the substrate and having a polarity lower than that of the first affinity group.

Further, the present invention provides a liquid crystal composition which contains the alignment aid of the present invention and liquid crystal molecules and has a negative dielectric anisotropy (Δ ∈).

Further, the present invention provides a liquid crystal display element comprising: two substrates, and a liquid crystal layer comprising the liquid crystal composition of the present invention provided between the two substrates.

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, an alignment aid which has excellent storage stability and can perform uniform vertical alignment of liquid crystal molecules even when a PI layer is omitted, a liquid crystal composition containing the alignment aid, and a liquid crystal display element using the liquid crystal composition can be provided.

Drawings

Fig. 1 is a diagram schematically showing an embodiment of a liquid crystal display element.

Fig. 2 is an enlarged plan view of the area surrounded by the line I in fig. 1.

Detailed Description

Hereinafter, the alignment aid, the liquid crystal composition, and the liquid crystal display element of the present invention will be described in detail based on preferred embodiments.

(orientation aid)

The alignment assistant of the present invention is arranged between the two substrates together with the liquid crystal molecules, and thus can align the liquid crystal molecules spontaneously. The orientation aid contains: a first compound comprising at least one first affinity group having an affinity with respect to the substrate; and a second compound containing at least one second affinity group having an affinity for the substrate and having a polarity lower than that of the first affinity group.

The first compound and the second compound respectively include: an affinity group having an affinity for the substrate, and another moiety (other structure) having a lower affinity for the substrate than the affinity group.

Therefore, when a liquid crystal composition containing an alignment aid and liquid crystal molecules is supplied between two substrates to form a liquid crystal layer, both the first compound and the second compound can be disposed (aligned) so that the affinity group is adsorbed (attached) to the substrates and the other portion is separated from the substrates. By the presence of the first compound and the second compound arranged in this manner, a state in which liquid crystal molecules are aligned in the vertical direction can be maintained in the liquid crystal layer.

Here, the affinity group is adsorbed (attached) to the substrate and has a function of fixing the first compound and the second compound to the substrate, and may be referred to as an adsorptive group (an adhesive group), a PEG group, a sinker group (sinker group), or an anchor group.

According to the alignment aid of the present invention, even if the PI layer is omitted, the liquid crystal molecules can be aligned (vertical alignment of the liquid crystal molecules is induced when no voltage is applied, and horizontal alignment of the liquid crystal molecules is achieved when a voltage is applied). Thus, both the first compound and the second compound can be preferably used to assist the spontaneous alignment of the liquid crystal molecules in the liquid crystal layer.

The first affinity group and the second affinity group are different in polarity from each other, and particularly the first affinity group is more polar than the second affinity group. Therefore, when the liquid crystal composition is supplied onto the substrate, the first affinity group is adsorbed onto the substrate earlier than the second affinity group. As a result, the first compound is fixed to the substrate more preferentially than the second compound.

On the other hand, the second compound is uniformly wet-spread on the substrate and then fixed to the substrate. In this case, the second compound may be aligned (oriented) with respect to the first compound immobilized on the substrate as a reference (base).

In this case, the alignment aid of the present invention contains the first compound containing at least one first affinity group and the second compound containing a polar affinity group including the second compound containing the second affinity group, and thus can exert a more reliable alignment restraining force of the liquid crystal molecules (an effect of preventing the occurrence of alignment unevenness).

Further, since the first compound has a first affinity group having a high polarity, it tends to be easily precipitated when the amount of the first compound contained in the liquid crystal composition is increased.

The alignment aid of the present invention contains the second compound having the second affinity group having a relatively low polarity, and thus can prevent or suppress the precipitation of the first compound in the liquid crystal composition. This ensures the storage stability (particularly, the storage stability at low temperatures) of the liquid crystal composition.

Even if the amount of the first compound is reduced, the alignment assistant of the present invention exerts a sufficient alignment restriction force on the liquid crystal molecules by utilizing a synergistic effect with the second compound.

In addition, the ratio of the first compound to the second compound in the alignment aid is not particularly limited, but is preferably 1: 0.1-1: about 10, more preferably 1: 0.5-1: about 5. By containing the first compound and the second compound in such a ratio, the alignment assistant can surely exhibit both the effect of improving the alignment regulating force of the liquid crystal molecules and the effect of securing the storage stability of the liquid crystal composition.

The specific amounts of the first compound and the second compound to be used can be specified by the relationship with the amount of liquid crystal molecules when the liquid crystal composition is prepared.

The amount of the first compound is preferably about 0.1 to 1.5 wt%, and more preferably about 0.3 to 1.3 wt% with respect to 100 wt% of the liquid crystal molecules.

On the other hand, the amount of the second compound is also preferably about 0.1 to 1.5% by weight, more preferably about 0.3 to 1.3% by weight, based on 100% by weight of the liquid crystal molecules.

The total amount of the first compound and the second compound is preferably as small as possible (preferably 1.4 wt% or less, more preferably about 0.5 wt% to 1 wt% with respect to 100 wt% of the liquid crystal molecules) within a range in which the effect of improving the orientation constraint force of the liquid crystal molecules is required and sufficiently exhibited. This can further improve the storage stability of the liquid crystal composition.

The first affinity group and the second affinity group each preferably include a group selected from the following groups, and are substituents designed such that the polarity of the second affinity group is lower than that of the first affinity group.

[ solution 1]

(wherein the black dots represent the connecting keys.)

If the substituent is a substituent including a group selected from the above groups, the first affinity group and the second affinity group can be easily designed so that the polarity of the second affinity group is lower than the polarity of the first affinity group.

The first affinity group preferably includes a group selected from the group represented by formula 2 below, and more preferably selected from the group represented by general formulae (K1-1) to (K1-3) below.

[ solution 2]

[ solution 3]

In the formulae (K1-1) to (K1-3), the black dot at the left end represents a connecting bond,

W^K2represents methine, C-CH₃、C-C₂H₅A nitrogen atom or a silicon atom,

W^K3represents a carbon atom, and represents a carbon atom,

X₁～X₅each independently represents a hydrogen atom, -OH group or CH₂＝C(CH₃)COO-，

X₁And X₂At least one of them represents an-OH group,

X₃、X₄and X₅At least one of them represents an-OH group,

Sp₁、Sp₂and Sp₃Each represents a single bond or a spacer.

Examples of the spacer include-CH-CH-, -CF-CF-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF ≡ C-, -OCO-, -OCOO-, -C-O-C-O₂O-、-OCF₂-、-CH＝CHCOO-、-OCOCH＝CH-、-CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-or a branched or linear alkylene group having 1 to 20 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkylene group)₂-may be substituted by-O-, -COO-or-OCO-) is suitable.

Such a first affinity group has sufficiently high polarity, and therefore exhibits higher affinity (adsorption force) with respect to the substrate.

Sp₁、Sp₂And Sp₃Particularly preferably a single bond or a methylene group, respectively.

Specific examples of the first affinity group include substituents shown in the following groups.

[ solution 4]

(wherein the black dots represent the connecting keys.)

In the above group, when importance is attached to chemical stability as an alignment aid, the first affinity group is preferably K1-1, K1-2-1, K1-2-2, and K1-2-3. When importance is attached to the orientation of the liquid crystal molecules, the first affinity group is preferably K1-2-1, K1-2-2, and K1-2-3.

When importance is attached to solubility in the liquid crystal composition, the first affinity group is preferably K1-2-4, K1-3-1, K1-3-2, K1-3-3, K1-3-4, or K1-3-5. Further, when importance is attached to the balance of these groups, the first affinity group is more preferably K1-2-1, K1-2-2, K1-2-3, K1-3-1, K1-3-2, K1-3-3, and K1-3-4.

On the other hand, the second affinity group preferably includes a group selected from the group represented by formula 5 below, and more preferably selected from the group represented by general formulae (K2-1) to (K2-14) below.

[ solution 5]

[ solution 6]

In the formulae (K2-1) to (K2-14), the black dots at the left end represent the connecting bonds,

any of the methylene groups may be independently substituted with a linear or branched alkyl group having 1 to 5 carbon atoms, a linear or branched alkoxy group having 1 to 5 carbon atoms, or a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms,

W^K1represents methine, C-CH₃、C-C₂H₅Or a nitrogen atom, or a mixture of nitrogen atoms,

X^K1and Y^K1Each independently represents-CH₂-, an oxygen atom or a sulfur atom,

Z^K1represents an oxygen atom or a sulfur atom.

U^K1、V^K1And S^K1Each independently represents a methine group or a nitrogen atom (wherein U^K1Is methine, V^K1Is methine and S^K1Except for a combination of nitrogen atoms),

R^K1represents a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a linear or branched alkoxy group having 1 to 5 carbon atoms, or a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms.

The second compound containing such a second affinity group is apt to wet-spread more uniformly on the substrate.

In the above group, when importance is attached to chemical stability as an alignment aid, the second affinity group is preferably (K2-1), (K2-3), (K2-8), (K2-9) or (K2-13). When importance is attached to the orientation of the liquid crystal molecules, the second affinity group is preferably (K2-1) or (K2-3).

When importance is attached to solubility in the liquid crystal composition, the second affinity group is preferably (K2-1), (K2-9) or (K2-13). Further, when importance is attached to the balance of these groups, the second affinity group is more preferably (K2-1) or (K2-3).

Various combinations exist as the combination of the first affinity group and the second affinity group, but a combination of the first affinity group containing a hydroxyl group and the second affinity group containing an ether group or a carbonate group is preferable. By combining the first affinity group and the second affinity group, the polarity of the first affinity group can be sufficiently increased and the polarity of the second affinity group can be sufficiently lower than the polarity of the first affinity group. Therefore, both the effect of increasing the orientation constraint force of the liquid crystal molecules and the effect of ensuring the storage stability of the liquid crystal composition can be further enhanced.

The number of the first affinity group and the second affinity group may be one or more, respectively. By setting the number of the first affinity group and the second affinity group, the fixing force of the first compound and the second compound to the substrate can be adjusted.

In addition, the first compound and the second compound preferably each contain at least one polymerizable group. By polymerizing the polymerizable groups with each other, the first compound and the second compound can be more firmly fixed to the substrate, and the holding force of the liquid crystal molecules can be improved. As a result, the peeling of the liquid crystal layer from the substrate can be prevented or suppressed.

The number of the polymerizable groups may be one or more. By having a plurality of polymerizable groups, the crosslinking density of the first compound and the second compound can be increased. Therefore, they can be further firmly fixed to the substrate, and the holding force of the liquid crystal molecules can be further improved.

Such a polymerizable group is selected from the group represented by the following general formulae (P-1) to (P-13), for example.

[ solution 7]

(in the formula, the black dot at the right end represents a connection key.)

Since these polymerizable groups have high reactivity, polymerization can be sufficiently and reliably performed even with relatively low energy (e.g., light energy or heat energy). Therefore, when the first compound and the second compound are polymerized, deterioration of the liquid crystal molecules due to adverse effects can be prevented or suppressed.

Among these, the polymerizable group is preferably a group represented by the formulae (P-1) to (P-3), more preferably a group represented by the formulae (P-1) and (P-3).

The first compound and the second compound preferably each contain a liquid crystal proto (mesogen). Thus, the first affinity group and the second affinity group having a higher polarity than the mesogen can be adsorbed on the substrate, and the mesogen having a lower polarity can be more reliably disposed (aligned) so as to be separated from the substrate.

Since the first compound and the second compound contain a liquid crystal primordium, the first compound and the second compound have higher affinity with liquid crystal molecules. Therefore, the orientation constraint of the liquid crystal molecules by the first compound and the second compound can be further improved.

The first affinity group, the second affinity group, and the polymerizable group may be directly connected to the mesogen group, respectively, or may be connected to the mesogen group through the same spacer as described above. The position of the mesogen group to which the polymerizable group is bonded is not particularly limited, and is preferably a position close to the first affinity group or the second affinity group. Thus, the first compound and the second compound are polymerized and more firmly fixed to the substrate without adversely affecting the alignment of the liquid crystal molecules. Further, the polymerizable group is preferably bonded to the side with respect to the mesogen.

The mesogen is represented by, for example, the following general formula (i).

[ solution 8]

In the formula (i), the black dots at the left end and the black dots at the right end represent the connecting keys,

Aⁱ¹represents a divalent 6-membered cyclic aromatic group, a divalent 6-membered cyclic heteroaromatic group, a divalent 6-membered cycloaliphatic group or a divalent 6-membered cycloaliphatic group,

the hydrogen atom in the ring structure may be a halogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms or Pⁱ¹-Spⁱ¹-substituted, here, Pⁱ¹Represents a polymerizable group selected from the group represented by the general formulae (P-1) to (P-13), Spⁱ¹Is represented by the formula Zⁱ¹The same meaning is given to the same person,

Zⁱ¹represents a single bond, -CH-, -CF-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF₂O-、-OCF₂-、-CH＝CHCOO-、-OCOCH＝CH-、-CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-or alkylene having 2 to 20 carbon atoms (wherein one or two or more-CH groups not adjacent to each other in the alkylene group₂May be substituted by-O-, -COO-or-OCO-),

mⁱ¹represents an integer of 1 to 5, and a salt thereof,

at mⁱ¹When the number is 2 or more, a plurality of Aⁱ¹May be the same or different from each other.

Preferably Z in formula (i)ⁱ¹Represents a single bond, -CH ═ CH-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CH ═ CHCOO-, -OCOCH ═ CH-, -CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-or a linear or branched alkylene group having 2 to 20 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkylene group)₂-may be substituted by-O-).

More preferably Z in the formula (i)ⁱ¹Represents a single bond, -COO-, -OCO-, -CH ═ CHCOO-, -OCOCH ═ CH-, -CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-, or a linear or branched alkylene group having 2 to 15 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkylene group₂-may be substituted by-O-).

More preferably Z in the formula (i)ⁱ¹Represents a single bond, -CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-, or alkylene having 2 carbon atoms (ethylene (-CH)₂CH₂-) or-CH in ethylene₂One of (1) is-O-substituted group (-CH)₂O-、-OCH₂-) or a linear alkylene group having 3 to 13 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkylene group₂-may be substituted by-O-).

Preferably A in formula (i)ⁱ¹Represents a divalent 6-membered ring aromatic group or a divalent 6-membered ring aliphatic group. Here, examples of the divalent 6-membered cyclic aromatic group or divalent 6-membered cyclic aliphatic group include: a divalent unsubstituted 6-membered cyclic aromatic group, a divalent unsubstituted 6-membered cyclic aliphatic group, or a cyclic structure thereof wherein the hydrogen atom is substituted by a halogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms or Pⁱ¹-Spⁱ¹-substituted radicals. Here, Pⁱ¹Represents a polymerizable group selected from the group represented by the general formulae (P-1) to (P-13), Spⁱ¹Is represented by the formula Zⁱ¹The same meaning is used.

Of these, A in the formula (i)ⁱ¹Preferably a divalent unsubstituted 6-membered cyclic aromatic group, a cyclic structure in which hydrogen atoms are bonded via halogen atoms (particularly fluorine atoms), a C1-10 linear or branched alkyl group, a C1-10 linear or branched alkoxy group or Pⁱ¹-Spⁱ¹A divalent 6-membered cyclic aromatic group, a divalent unsubstituted 6-membered cyclic aliphatic group, a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms or P, wherein the hydrogen atom in the cyclic structure is a halogen atom (particularly a fluorine atom), and the alkyl group is a divalent 6-membered cyclic aromatic group, a divalent unsubstituted 6-membered cyclic aliphatic group, a linear or branched alkoxy group having 1 to 10 carbon atomsⁱ¹-Spⁱ¹A divalent 6-membered cyclic aliphatic group, more preferably a cyclic aliphatic group, wherein the hydrogen atom in the cyclic structure may be replaced by a halogen atom (particularly, a fluorine atom), the alkyl group, the alkoxy group or Pⁱ¹-Spⁱ¹-substituted 1, 4-phenylene, 2, 6-naphthylene or 1, 4-cyclohexyl.

Note that m isⁱ¹Preferably represents an integer of 2 to 5, more preferably an integer of 2 to 4.

Further, the mesogen represented by the general formula (i) may be in the repeating unit- (A)ⁱ¹-Zⁱ¹) The intermediate portion of (a) includes a branched structure of any one of trivalent and tetravalent, or an aliphatic or aromatic ring structure of any one of trivalent and tetravalent. In this case, the first compound and the second compound each have a branched structure as a whole.

Further, the first compound and the second compound preferably each include a terminal group connected to the liquid crystal ortho-group on the opposite side to the first affinity group or the second affinity group. The first compound and the second compound each having a terminal group are easily arranged (oriented) so that the affinity group is adsorbed to the substrate and the other portion than the affinity group is separated from the substrate.

Examples of the terminal group include: a C1-40 linear or branched alkyl group, a C1-40 linear or branched halogenated alkyl group (wherein-CH in the alkyl group or halogenated alkyl group)₂-may be substituted with-CH ═ CH-, -C ≡ C-, -O-, -NH-, -COO-, or-OCO-, but-O-is not continuous. ) Or a polymerizable group bonded to the mesogen directly or via a spacer.

The polymerizable group and the spacer are the same as the polymerizable group and the spacer described above, respectively. When the first compound and the second compound each contain a polymerizable group as an end group, the crosslinking density of the first compound and the second compound can be further increased, and the holding power of liquid crystal molecules in the liquid crystal layer can be further increased.

Specific examples of the first compound include compounds represented by any one of the following formulae (PJ-I-1) to (PJ-I-45).

[ solution 9]

[ solution 10]

[ solution 11]

[ solution 12]

[ solution 13]

[ solution 14]

[ solution 15]

[ solution 16]

[ solution 17]

On the other hand, specific examples of the second compound include compounds represented by any one of the following formulas (PJ-II-1) to (PJ-II-18).

[ solution 18]

[ solution 19]

[ solution 20]

[ solution 21]

(liquid Crystal composition)

The liquid crystal composition of the present invention contains an alignment assistant (first compound and second compound) and liquid crystal molecules, and has a negative dielectric anisotropy (Δ ∈).

The liquid crystal molecules preferably contain a compound selected from the group represented by the following general formulae (N-1) to (N-3).

[ solution 22]

In the general formula (N-1), the general formula (N-2) and the general formula (N-3), R^N11、R^N12、R^N21、R^N22、R^N31And R^N32Each independently represents an alkyl group having 1 to 8 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-.

A^N11、A^N12、A^N21、A^N22、A^N31And A^N32Each independently represents a group selected from the group consisting of,

(a)1, 4-cyclohexylene (wherein one-CH group is present in the radical)₂-or two or more-CH's which are not contiguous₂-may be substituted by-O-),

(b)1, 4-phenylene (in which one or two or more-CH-groups present in the group may be substituted by-N-),

(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (wherein one or two or more-CH ═ s which are not adjacent to each other and are present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted with-N), and

(d)1, 4-Cyclohexenylene group

The aforementioned group (a), group (b), group (c) and group (d) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom.

In addition, Z^N11、Z^N12、Z^N21、Z^N22、Z^N31And Z^N32Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

X^N21represents a hydrogen atom or a fluorine atom,

T^N31represents-CH₂-or an oxygen atom.

n^N11、n^N12、n^N21、n^N22、n^N31And n^N32Each independently represents an integer of 0 to 3, with n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Independently of one another is 1,2 or 3,

in A^N11～A^N32、Z^N11～Z^N32When a plurality of the compounds are present, they may be the same or different from each other.

Any of the compounds of the general formula (N-1), the general formula (N-2) and the general formula (N-3) is preferably a compound having negative Δ ε and an absolute value of more than 3.

In the general formula (N-1), the general formula (N-2) and the general formula (N-3), R^N11、R^N12、R^N21、R^N22、R^N31And R^N32Preferably independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, more preferably 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, still more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, particularly preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, most preferablyAn alkenyl group having 3 carbon atoms (propenyl group).

In addition, R^N11、R^N12、R^N21、R^N22、R^N31And R^N32When the ring structure to which these are bonded is a phenyl group (aromatic group), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferable, and when the ring structure to which these are bonded is a saturated ring structure such as cyclohexane, pyran, dioxane, or the like, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from the group represented by any one of the formulae (R1) to (R5).

[ solution 23]

(Black dots in the formulae represent connecting keys.)

To increase Δ n, A^N11、A^N12、A^N21、A^N22、A^N31And A^N32Preferably independently of one another, an aromatic group, A for improving the response speed^N11、A^N12、A^N21、A^N22、A^N31And A^N32Preferably independently of each other, an aliphatic group.

The aromatic group or aliphatic group preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the structure of the following chemical formula 24, more preferably represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene group.

[ solution 24]

Z^N11、Z^N12、Z^N21、Z^N22、Z^N31And Z^N32Preferably each independently represents-CH₂O-、-CF₂O-、-CH₂CH₂-、-CF₂CF₂-or a single bond, more preferably-CH₂O-、-CH₂CH₂-or a single bond, particularly preferably-CH₂O-or a single bond.

X^N21Preferably a fluorine atom.

T^N31Preferably an oxygen atom.

n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Preferably each independently 1 or 2, more preferably n^N11Is 1 and n^N12A combination of 0, n^N11Is 2 and n^N12A combination of 0, n^N11Is 1 and n^N12Is a combination of 1, n^N11Is 2 and n^N12Is a combination of 1, n^N21Is 1 and n^N22A combination of 0, n^N21Is 2 and n^N22A combination of 0, n^N31Is 1 and n^N32A combination of 0, n^N31Is 2 and n^N32Is a combination of 0.

The lower limit of the preferable content of the compound represented by the formula (N-1) relative to the total amount of the liquid crystal composition is 1 mass% or more, 10 mass% or more, 20 mass% or more, 30 mass% or more, 40 mass% or more, 50 mass% or more, 55 mass% or more, 60 mass% or more, 65 mass% or more, 70 mass% or more, 75 mass% or more, and 80 mass% or more.

On the other hand, the upper limit of the content is preferably 95 mass% or less, 85 mass% or less, 75 mass% or less, 65 mass% or less, 55 mass% or less, 45 mass% or less, 35 mass% or less, 25 mass% or less, or 20 mass% or less.

The lower limit of the preferable content of the compound represented by the formula (N-2) relative to the total amount of the liquid crystal composition is 1 mass% or more, 10 mass% or more, 20 mass% or more, 30 mass% or more, 40 mass% or more, 50 mass% or more, 55 mass% or more, 60 mass% or more, 65 mass% or more, 70 mass% or more, 75 mass% or more, and 80 mass% or more.

The lower limit of the preferable content of the compound represented by the formula (N-3) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 10 mass% or more, 20 mass% or more, 30 mass% or more, 40 mass% or more, 50 mass% or more, 55 mass% or more, 60 mass% or more, 65 mass% or more, 70 mass% or more, 75 mass% or more, and 80 mass% or more.

When it is necessary to keep the viscosity of the liquid crystal composition low and the response speed is high, the lower limit value and the upper limit value are preferably low. Further, when it is necessary to maintain the nematic phase-isotropic liquid phase transition temperature (Tni) of the liquid crystal composition high and the liquid crystal composition has good temperature stability, it is preferable that the lower limit value is low and the upper limit value is low. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the lower limit and increase the upper limit.

The compounds represented by the general formula (N-1) include compounds represented by the following general formulae (N-1a) to (N-1 g).

[ solution 25]

In the formulae (N-1a) to (N-1g), R^N11And R^N12R in the general formula (N-1)^N11And R^N12Same meaning, n^Na11Represents 0 or 1, n^Nb11Represents 0 or 1, n^Nc11Represents 0 or 1, n^Nd11Represents 0 or 1, n^Ne11Represents 1 or 2, n^Nf11Represents 1 or 2, n^Ng11Represents 1 or 2, A^Ne11Represents trans-1, 4-cyclohexylene or 1, 4-phenylene, A^Ng11Represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene, but at least one represents 1, 4-cyclohexenylene, Z^Ne11Represents a single bond or an ethylene group, but at least one represents an ethylene group.

More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group consisting of compounds represented by the general formulae (N-1-1) to (N-1-21).

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

[ solution 26]

(in the formula, R^N111And R^N112Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a propyl group, a pentyl group or a vinyl group. R^N112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group or a butoxy group.

The compounds represented by the general formula (N-1-1) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

When importance is attached to improvement of Δ ∈, it is preferable to set the content slightly higher, and when importance is attached to solubility at low temperatures, the effect is high if the content is set slightly higher, and when importance is attached to Tni, the effect is high if the content is set slightly lower. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-1) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, and 35 mass% or more.

On the other hand, the upper limit of the content is preferably 50% by mass or less, 40% by mass or less, 38% by mass or less, 35% by mass or less, 33% by mass or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, 13% by mass or less, 10% by mass or less, 8% by mass or less, 7% by mass or less, 6% by mass or less, 5% by mass or less, and 3% by mass or less.

Further, the compound represented by the general formula (N-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-1.1) to (N-1-1.22), more preferably a compound represented by the formulae (N-1-1.1) to (N-1-1.4), and still more preferably a compound represented by the formulae (N-1-1.1) and (N-1-1.3).

[ solution 27]

The compounds represented by the formulae (N-1-1.1) to (N-1-1.22) may be used alone or in combination.

The lower limit of the preferable content of the compound represented by the formulae (N-1-1.1) to (N-1-1.22) (alone or in combination) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, and 35 mass% or more.

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

[ solution 28]

(in the formula, R^N121And R^N122Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group or a pentyl group. R^N122Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.

The compounds represented by the general formula (N-1-2) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

When importance is attached to improvement of Δ ∈, it is preferable to set the content slightly higher, and when importance is attached to solubility at low temperatures, the effect is high if the content is set slightly lower, and when importance is attached to Tni, the effect is high if the content is set slightly higher. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-2) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, 35 mass% or more, 37 mass% or more, 40 mass% or more, and 42 mass% or more.

On the other hand, the upper limit of the preferable content is 50 mass% or less, 48 mass% or less, 45 mass% or less, 43 mass% or less, 40 mass% or less, 38 mass% or less, 35 mass% or less, 33 mass% or less, 30 mass% or less, 28 mass% or less, 25 mass% or less, 23 mass% or less, 20 mass% or less, 18 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, 8 mass% or less, 7 mass% or less, 6 mass% or less, and 5 mass% or less.

Further, the compound represented by the general formula (N-1-2) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-2.1) to (N-1-2.22), and more preferably a compound represented by the formulae (N-1-2.3) to (N-1-2.7), (N-1-2.10), (N-1-2.11), (N-1-2.13) or (N-1-2.20).

The compounds represented by the formulae (N-1-2.3) to (N-1-2.7) are preferable when the improvement of Δ ε is important, the compounds represented by the formulae (N-1-2.10), (N-1-2.11) and (N-1-2.13) are preferable when the improvement of Tni is important, and the compounds represented by the formulae (N-1-2.20) are preferable when the improvement of response speed is important.

[ solution 29]

The compounds represented by the formulae (N-1-2.1) to (N-1-2.22) may be used alone or in combination.

The lower limit of the preferable content of the compound represented by the formulae (N-1-2.1) to (N-1-2.22) (alone or in combination) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, and 35 mass% or more.

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

[ solution 30]

(in the formula, R^N131And R^N132Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably a 1-propenyl group, ethoxy group, propoxy group or butoxy group.

The compounds represented by the general formula (N-1-3) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

When importance is attached to improvement of Δ ∈, it is preferable to set the content slightly higher, and when importance is attached to solubility at low temperatures, the effect is high if the content is set slightly higher, and when importance is attached to Tni, the effect is high if the content is set slightly higher. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-3) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

On the other hand, the upper limit of the preferable content is 35% by mass or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, and 13% by mass or less.

Further, the compound represented by the general formula (N-1-3) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-3.1) to (N-1-3.21), more preferably a compound represented by the formulae (N-1-3.1) to (N-1-3.7) and (N-1-3.21), and still more preferably a compound represented by the formulae (N-1-3.1), (N-1-3.2), (N-1-3.3), (N-1-3.4) and (N-1-3.6).

[ solution 31]

The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) may be used alone or in combination, but preferably are a combination of two or three selected from the group consisting of the formulae (N-1-3.3), (N-1-3.4) and (N-1-3.6) and the formula (N-1-3.1) and (N-1-3.2).

The lower limit of the preferable content of the compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) (used alone or in combination) is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more with respect to the total amount of the liquid crystal composition.

The compound represented by the general formula (N-1-4) is the following compound.

[ solution 32]

(in the formula, R^N141And R^N142Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N141And R^N142Each of the alkyl group and the alkenyl group is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably a methyl group, a propyl group, an ethoxy group, or a butoxy group.

The compounds represented by the general formula (N-1-4) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-4) with respect to the total amount of the liquid crystal composition is 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

On the other hand, the upper limit of the preferable content is 35% by mass or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, 13% by mass or less, 11% by mass or less, 10% by mass or less, or 8% by mass or less.

Further, the compound represented by the general formula (N-1-4) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-4.1) to (N-1-4.14), more preferably a compound represented by the formulae (N-1-4.1) to (N-1-4.4), and still more preferably a compound represented by the formulae (N-1-4.1), (N-1-4.2) and (N-1-4.4).

[ solution 33]

The compounds represented by the formulae (N-1-4.1) to (N-1-4.14) may be used alone or in combination.

The lower limit of the preferable content of the compound represented by the formulae (N-1-4.1) to (N-1-4.14) (alone or in combination) with respect to the total amount of the liquid crystal composition is 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

The compound represented by the general formula (N-1-5) is the following compound.

[ chemical 34]

(in the formula, R^N151And R^N152Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N151And R^N152Each of the alkyl group and the alkenyl group is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethyl group, a propyl group, or a butyl group.

The compounds represented by the general formula (N-1-5) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-5) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 8 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

On the other hand, the upper limit of the preferable content is 35% by mass or less, 33% by mass or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, and 13% by mass or less.

Further, the compound represented by the general formula (N-1-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-5.1) to (N-1-5.6), and more preferably a compound represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4).

[ solution 35]

The compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4) may be used alone or in combination.

The lower limit of the preferable content of the compound represented by the formula (N-1-5.1), the formula (N-1-5.2) or the formula (N-1-5.4) (used alone or in combination) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 8 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-10) is the following compound.

[ solution 36]

(in the formula, R^N1101And R^N1102Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1101Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R^N1102Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-10) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment of the present invention, the kind of the compound used is one kind, two kinds, three kinds, four kinds, five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-10) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

Further, the compound represented by the general formula (N-1-10) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-10.1) to (N-1-10.14), more preferably a compound represented by the formulae (N-1-10.1) to (N-1-10.5), and still more preferably a compound represented by the formulae (N-1-10.1) and (N-1-10.2).

[ solution 37]

The compounds represented by the formulae (N-1-10.1) and (N-1-10.2) may be used alone or in combination.

The lower limit of the preferable content of the compounds represented by the formulae (N-1-10.1) and (N-1-10.2) (alone or in combination) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

The compound represented by the general formula (N-1-11) is the following compound.

[ solution 38]

(in the formula, R^N1111And R^N1112Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R^N1112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-11) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

When importance is attached to improvement of Δ ∈, it is preferable to set the content slightly higher, when importance is attached to solubility at low temperatures, the effect is high if the content is set slightly lower, and when importance is attached to Tni, the effect is high if the content is set slightly higher. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-11) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

Further, the compound represented by the general formula (N-1-11) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-11.1) to (N-1-11.14), and more preferably a compound represented by the formulae (N-1-11.2) and (N-1-11.4).

[ solution 39]

The compounds represented by the formulae (N-1-11.2) and (N-1-11.4) may be used alone or in combination.

The lower limit of the preferable content of the compounds represented by the formulae (N-1-11.2) and (N-1-11.4) (alone or in combination) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

The compound represented by the general formula (N-1-12) is the following compound.

[ solution 40]

(in the formula, R^N1121And R^N1122Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N1122Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, more preferablyIs ethoxy, propoxy or butoxy.

The compounds represented by the general formula (N-1-12) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-12) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-13) is the following compound.

[ solution 41]

(in the formula, R^N1131And R^N1132Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N1132Preferably an alkyl group having 1 to 5 carbon atoms, or a C24-5 alkenyl or C1-4 alkoxy, more preferably ethoxy, propoxy or butoxy.

The compounds represented by the general formula (N-1-13) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-13) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-14) is the following compound.

[ solution 42]

(in the formula, R^N1141And R^N1142Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1141Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N1142Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-14) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment of the present invention, the kind of the compound used is one kind, two kinds, three kinds, four kinds, five kinds or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-14) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-15) is the following compound.

[ solution 43]

(in the formula, R^N1151And R^N1152Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1151Preferably an alkyl group having 1 to 5 carbon atoms or a carbonAn alkenyl group having 2 to 5 atoms, more preferably an ethyl group, a propyl group or a butyl group. R^N1152Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-15) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-15) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compounds represented by the general formula (N-1-16) are the following compounds.

[ solution 44]

(in the formula, R^N1161And R^N1162Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1161Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N1162Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-16) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-16) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-17) is the following compound.

[ solution 45]

(in the formula, R^N1171And R^N1172Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1171Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group. R^N1172Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-17) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-17) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compounds represented by the general formula (N-1-18) are the following compounds.

[ solution 46]

(in the formula, R^N1181And R^N1182Are respectively independentAnd (b) represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1181Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group or a butyl group. R^N1182Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-18) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-18) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

Further, the compound represented by the general formula (N-1-18) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-18.1) to (N-1-18.5), more preferably a compound represented by the formulae (N-1-18.1) to (N-1-18.3), and still more preferably a compound represented by the formulae (N-1-18.2) and (N-1-18.3).

[ solution 47]

The compound represented by the general formula (N-1-20) is the following compound.

[ solution 48]

(in the formula, R^N1201And R^N1202Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1201And R^N1202Each of the alkyl groups is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-20) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-20) relative to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-21) is the following compound.

[ solution 49]

(in the formula, R^N1211And R^N1212Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1211And R^N1212Each of the alkyl groups is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-21) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-21) with respect to the total amount of the liquid crystal composition is 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

The compound represented by the general formula (N-1-22) is the following compound.

[ solution 50]

(in the formula, R^N1221And R^N1222Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1221And R^N1222Each of the alkyl groups is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-22) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-1-21) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, and 20 mass% or more.

On the other hand, the upper limit of the preferable content is 35% by mass or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, 13% by mass or less, 10% by mass or less, and 5% by mass or less.

Further, the compound represented by the general formula (N-1-22) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-22.1) to (N-1-22.12), more preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.5), and still more preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.4).

[ solution 51]

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

[ solution 52]

(in the formula, R^N321And R^N322Each independently represents R in the general formula (N-3)^N11And R^N12The same meaning is used. )

R^N321And R^N322Each of the alkyl groups is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a propyl group or a pentyl group.

The compounds represented by the general formula (N-3-2) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (N-3-2) with respect to the total amount of the liquid crystal composition is 3 mass% or more, 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, or 35 mass% or more.

On the other hand, the upper limit of the preferable content is 50 mass% or less, 40 mass% or less, 38 mass% or less, 35 mass% or less, 33 mass% or less, 30 mass% or less, 28 mass% or less, 25 mass% or less, 23 mass% or less, 20 mass% or less, 18 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, 8 mass% or less, 7 mass% or less, 6 mass% or less, 5 mass% or less.

Further, the compound represented by the general formula (N-3-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-3-2.1) to (N-3-2.3).

[ Hua 53]

The liquid crystal molecules may further include a compound represented by the following general formula (L).

[ solution 54]

In the formula (L), R^L1And R^L2Each independently represents an alkyl group having 1 to 8 carbon atoms (wherein one or two or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-. ),

n^L1represents 0, 1,2 or 3.

A^L1、A^L2And A^L3Each independently represents a group selected from the group consisting of,

(b)1, 4-phenylene (in which one or two or more-CH-groups present in the group may be substituted by-N), and

(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, or decahydronaphthalene-2, 6-diyl (wherein one or two or more-CH ═ s present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by — N ═ s),

the group (a), the group (b) and the group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom.

Z^L1And Z^L2Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

at n^L1Is 2 or 3 and A^L2When plural, they may be the same or different from each other, and n is^L1Is 2 or 3 and Z^L2When a plurality of them are present, they may be the same or different from each other, except for the compounds represented by the general formula (N-1), the general formula (N-2) and the general formula (N-3).

The compound represented by the general formula (L) corresponds to a compound having a substantially neutral dielectric property (Δ ε has a value of-2 to 2). The compounds represented by the general formula (L) may be used alone or in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, as an embodiment, the kind of the compound used is one. Or two, three, four, five, six, seven, eight, nine, ten or more in another embodiment.

The amount of the compound represented by the general formula (L) contained in the liquid crystal composition is desirably adjusted depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by formula (L) relative to the total amount of the liquid crystal composition is 1 mass% or more, 10 mass% or more, 20 mass% or more, 30 mass% or more, 40 mass% or more, 50 mass% or more, 55 mass% or more, 60 mass% or more, 65 mass% or more, 70 mass% or more, 75 mass% or more, or 80 mass% or more.

On the other hand, the upper limit of the content is preferably 95 mass% or less, 85 mass% or less, 75 mass% or less, 65 mass% or less, 55 mass% or less, 45 mass% or less, 35 mass% or less, or 25 mass% or less.

When it is necessary to keep the viscosity of the liquid crystal composition low and the response speed is high, the lower limit value and the upper limit value are preferably high. Further, when it is necessary to maintain Tni of the liquid crystal composition high and the liquid crystal composition has good temperature stability, it is preferable that the lower limit value is high and the upper limit value is high. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to lower the lower limit and lower the upper limit.

In case reliability is important, R^L1And R^L2Preferably both are alkyl, and where importance is placed on reducing the volatility of the compound, R is^L1And R^L2Preferably, all are alkoxy groups, and when importance is attached to the reduction in viscosity, at least one is preferably an alkenyl group.

The number of halogen atoms present in the molecule is preferably 0, 1,2 or 3, more preferably 0 or 1, and when importance is attached to compatibility with other liquid crystal molecules, preferably 1.

R^L1And R^L2When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is a saturated ring structure such as cyclohexane, pyran, dioxane, or the likeIn the case of the cyclic structure (A) and (B), the cyclic structure is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.

[ solution 55]

(Black dots in the formulae represent connecting keys.)

In the case where importance is attached to the response speed, n^L1Preferably 0, n for improving the upper temperature limit of the nematic phase^L1Preferably 2 or 3, n for achieving their equilibrium^L1Preferably 1. In addition, in order to satisfy the characteristics required as a liquid crystal composition, it is preferable to combine compounds having different values.

In the case of a requirement to increase Δ n, A^L1、A^L2And A^L3Preferably aromatic, in order to improve the response speed, A^L1、A^L2And A^L3Preferably aliphatic, and preferably each independently represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably has the structure of the following formula 56, and still more preferably represents trans-1, 4-cyclohexylene or 1, 4-phenylene.

[ solution 56]

In the case where importance is attached to the response speed, Z^L1And Z^L2Preferably a single bond.

The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.

The compound represented by the general formula (L) is preferably a compound selected from the group consisting of compounds represented by the general formulae (L-1) to (L-7).

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

[ solution 57]

(in the formula, R^L11And R^L12Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L11And R^L12Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a straight chain of 2 to 5 carbon atoms.

The compounds represented by the general formula (L-1) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (L-1) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 15 mass% or more, 20 mass% or more, 25 mass% or more, 30 mass% or more, 35 mass% or more, 40 mass% or more, 45 mass% or more, 50 mass% or more, and 55 mass% or more.

On the other hand, the upper limit of the content is preferably 95% by mass or less, 90% by mass or less, 85% by mass or less, 80% by mass or less, 75% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less, 55% by mass or less, 50% by mass or less, 45% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, and 25% by mass or less.

When it is necessary to keep the viscosity of the liquid crystal composition low and the response speed is high, the lower limit value and the upper limit value are preferably high. Further, when it is necessary to maintain Tni of the liquid crystal composition high and the liquid crystal composition has good temperature stability, it is preferable that the lower limit value is centered and the upper limit value is centered. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the lower limit value and the upper limit value are preferably low.

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

[ solution 58]

(in the formula, R^L12Represents the same meaning as in the general formula (L-1). )

The compound represented by the general formula (L-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-1.1) to (L-1-1.3), more preferably a compound represented by the formula (L-1-1.2) or (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3).

[ chemical 59]

The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, and 10 mass% or more.

On the other hand, the upper limit of the content is preferably 20 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, 8 mass% or less, 7 mass% or less, 6 mass% or less, 5 mass% or less, or 3 mass% or less.

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

[ solution 60]

The lower limit of the preferable content of the compound represented by the formula (L-1-2) relative to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, or 35 mass% or more.

On the other hand, the upper limit of the content is preferably 60 mass% or less, 55 mass% or less, 50 mass% or less, 45 mass% or less, 42 mass% or less, 40 mass% or less, 38 mass% or less, 35 mass% or less, 33 mass% or less, or 30 mass% or less.

Further, the compound represented by the general formula (L-1-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-2.1) to (L-1-2.4), and more preferably a compound represented by the formulae (L-1-2.2) to (L-1-2.4). In particular, the compound represented by the formula (L-1-2.2) is preferable because it improves the response speed of the liquid crystal composition. When higher Tni is required than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L-1-2.4).

In order to improve the solubility at low temperatures, it is not preferable that the amount of the compound represented by the formula (L-1-2.3) or the formula (L-1-2.4) contained in the liquid crystal composition is 30% by mass or more.

[ solution 61]

The lower limit of the preferable content of the compound represented by the formula (L-1-2.2) with respect to the total amount of the liquid crystal composition is 10 mass% or more, 15 mass% or more, 18 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, 35 mass% or more, 38 mass% or more, and 40 mass% or more.

On the other hand, the upper limit of the content is preferably 60% by mass or less, 55% by mass or less, 50% by mass or less, 45% by mass or less, 43% by mass or less, 40% by mass or less, 38% by mass or less, 35% by mass or less, 32% by mass or less, 30% by mass or less, 27% by mass or less, 25% by mass or less, or 22% by mass or less.

The lower limit of the total preferable content of the compound represented by the formula (L-1-2.3) and the compound represented by the formula (L-1-2.4) relative to the total amount of the liquid crystal composition is 10 mass% or more, 15 mass% or more, 20 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 35 mass% or more, and 40 mass% or more.

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

[ solution 62]

(in the formula, R^L13And R^L14Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. )

R^L13And R^L14Preferably, the alkyl group is a linear alkyl group having 1 to 5 carbon atoms, the alkoxy group is a linear alkoxy group having 1 to 4 carbon atoms, or the alkenyl group is a linear alkenyl group having 2 to 5 carbon atoms.

The lower limit of the preferable content of the compound represented by the formula (L-1-3) relative to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, or 30 mass% or more.

On the other hand, the upper limit of the preferable content is 60 mass% or less, 55 mass% or less, 50 mass% or less, 45 mass% or less, 40 mass% or less, 37 mass% or less, 35 mass% or less, 33 mass% or less, 30 mass% or less, 27 mass% or less, 25 mass% or less, 23 mass% or less, 20 mass% or less, 17 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less.

Further, the compound represented by the general formula (L-1-3) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-3.1) to (L-1-3.13), and more preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) or the formula (L-1-3.4). In particular, the compound represented by the formula (L-1-3.1) is preferable because it improves the response speed of the liquid crystal composition. When higher Tni is required than the response speed, it is preferable to use compounds represented by the formulae (L-1 to 3.3), (L-1 to 3.4), (L-1 to 3.11) and (L-1 to 3.12).

In order to improve the solubility at low temperatures, it is not preferable that the total amount of the compounds represented by the formulae (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.12) contained in the liquid crystal composition is 20% by mass or more.

[ solution 63]

The lower limit of the preferable content of the compound represented by the formula (L-1-3.1) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 18 mass% or more, or 20 mass% or more.

On the other hand, the upper limit of the content is preferably 20 mass% or less, 17 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, 8 mass% or less, 7 mass% or less, or 6 mass% or less.

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

[ solution 64]

(in the formula, R^L15And R^L16Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. )

R^L15And R^L16Preferably, the alkyl group is a linear alkyl group having 1 to 5 carbon atoms, the alkoxy group is a linear alkoxy group having 1 to 4 carbon atoms, or the alkenyl group is a linear alkenyl group having 2 to 5 carbon atoms.

The lower limit of the preferable content of the compound represented by the formula (L-1-4) relative to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

On the other hand, the upper limit of the content is preferably 25% by mass or less, 23% by mass or less, 20% by mass or less, 17% by mass or less, 15% by mass or less, 13% by mass or less, or 10% by mass or less.

The lower limit of the preferable content of the compound represented by the formula (L-1-5) relative to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 17 mass% or more, or 20 mass% or more.

Further, the compounds represented by the general formulae (L-1-4) and (L-1-5) are preferably compounds selected from the group consisting of the compounds represented by the formulae (L-1-4.1) to (L-1-4.3) and (L-1-5.1) to (L-1-5.3), and more preferably compounds represented by the formulae (L-1-4.2) or (L-1-5.2).

[ solution 65]

The lower limit of the preferable content of the compound represented by the formula (L-1-4.2) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 18 mass% or more, or 20 mass% or more.

Preferably, two or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), (L-1-3.1), (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.12) are combined, and more preferably two or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), (L-1-3.1), (L-1-3.3), (L-1-3.4) and (L-1-4.2) are combined.

The lower limit of the total content of these compounds with respect to the total amount of the liquid crystal composition is preferably 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 13 mass% or more, 15 mass% or more, 18 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, 33 mass% or more, or 35 mass% or more.

On the other hand, the upper limit of the total content is preferably 80 mass% or less, 70 mass% or less, 60 mass% or less, 50 mass% or less, 45 mass% or less, 40 mass% or less, 37 mass% or less, 35 mass% or less, 33 mass% or less, 30 mass% or less, 28 mass% or less, 25 mass% or less, 23 mass% or less, or 20 mass% or less.

When importance is attached to the reliability of the liquid crystal composition, it is preferable to combine two or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-3.1), (L-1-3.3) and (L-1-3.4), and when importance is attached to the response speed of the liquid crystal composition, it is preferable to combine two or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3) and (L-1-2.2).

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-6).

[ solution 66]

(in the formula, R^L17And R^L18Each independently represents a methyl group or a hydrogen atom. )

The lower limit of the preferable content of the compound represented by the formula (L-1-6) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 5 mass% or more, 10 mass% or more, 15 mass% or more, 17 mass% or more, 20 mass% or more, 23 mass% or more, 25 mass% or more, 27 mass% or more, 30 mass% or more, or 35 mass% or more.

Further, the compound represented by the general formula (L-1-6) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-6.1) to (L-1-6.3).

[ solution 67]

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

[ solution 68]

(in the formula, R^L21And R^L22Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L21Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L22Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compounds represented by the general formula (L-2) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

When importance is attached to the solubility at low temperature, the effect is high if the content is set to be slightly large, whereas when importance is attached to the response speed, the effect is high if the content is set to be slightly small. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (L-2) relative to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, and 10 mass% or more.

Further, the compound represented by the general formula (L-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-2.1) to (L-2.6), and more preferably a compound represented by the formulae (L-2.1), (L-2.3), (L-2.4) and (L-2.6).

[ solution 69]

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

[ solution 70]

(in the formula, R^L31And R^L32Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L31And R^L32Preferably, each of the alkyl groups is independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

The compounds represented by the general formula (L-3) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by the formula (L-3) with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, and 10 mass% or more.

When a high birefringence is obtained, the effect is high if the content is set to be slightly large, and conversely, when high Tni is emphasized, the effect is high if the content is set to be slightly small. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

Further, the compound represented by the general formula (L-3) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-3.1) to (L-3.7), and more preferably a compound represented by the formulae (L-3.2) to (L-3.7).

[ solution 71]

The compound represented by the general formula (L-4) is the following compound.

[ chemical formula 72]

(in the formula, R^L41And R^L42Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L41Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L42Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compounds represented by the general formula (L-4) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The content of the compound represented by the general formula (L-4) in the liquid crystal composition is desirably adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-4) relative to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 14 mass% or more, 16 mass% or more, 20 mass% or more, 23 mass% or more, 26 mass% or more, 30 mass% or more, 35 mass% or more, or 40 mass% or more.

On the other hand, the upper limit of the content is preferably 50% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, or 5% by mass or less.

The compound represented by the general formula (L-4) is preferably a compound represented by, for example, the formulae (L-4.1) to (L-4.3).

[ solution 73]

The compound represented by the formula (L-4.1), the compound represented by the formula (L-4.2), both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2), or all of the compounds represented by the formulae (L-4.1) to (L-4.3) may be contained in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like.

The lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) with respect to the total amount of the liquid crystal composition is 3 mass% or more, 5 mass% or more, 7 mass% or more, 9 mass% or more, 11 mass% or more, 12 mass% or more, 13 mass% or more, 18 mass% or more, 21 mass% or more.

On the other hand, the upper limit of the content is preferably 45 mass% or less, 40 mass% or less, 35 mass% or less, 30 mass% or less, 25 mass% or less, 23 mass% or less, 20 mass% or less, 18 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, or 8 mass% or less.

When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the lower limit of the preferable content of both compounds relative to the total amount of the liquid crystal composition is 15 mass% or more, 19 mass% or more, 24 mass% or more, and 30 mass% or more.

On the other hand, the upper limit of the content is preferably 45 mass% or less, 40 mass% or less, 35 mass% or less, 30 mass% or less, 25 mass% or less, 23 mass% or less, 20 mass% or less, 18 mass% or less, 15 mass% or less, or 13 mass% or less.

The compound represented by the general formula (L-4) is preferably a compound represented by the formula (L-4.4) to the formula (L-4.6), and more preferably a compound represented by the formula (L-4.4).

[ chemical formula 74]

The compound represented by the formula (L-4.4), the compound represented by the formula (L-4.5), or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like.

The lower limit of the preferable content of the compound represented by the formula (L-4.4) or the formula (L-4.5) with respect to the total amount of the liquid crystal composition is 3 mass% or more, 5 mass% or more, 7 mass% or more, 9 mass% or more, 11 mass% or more, 12 mass% or more, 13 mass% or more, 18 mass% or more, 21 mass% or more.

When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the lower limit of the preferable content of both the compounds with respect to the total amount of the liquid crystal composition is 15 mass% or more, 19 mass% or more, 24 mass% or more, and 30 mass% or more.

The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.7) to (L-4.10), and particularly preferably a compound represented by the formula (L-4.9).

[ solution 75]

The compound represented by the general formula (L-5) is the following compound.

[ 76]

(in the formula, R^L51And R^L52Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L51Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L52Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compounds represented by the general formula (L-5) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The content of the compound represented by the general formula (L-5) in the liquid crystal composition is desirably adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by formula (L-5) relative to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 14 mass% or more, 16 mass% or more, 20 mass% or more, 23 mass% or more, 26 mass% or more, 30 mass% or more, 35 mass% or more, or 40 mass% or more.

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

[ solution 77]

The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, and 7 mass% or more.

On the other hand, the upper limit of the content is preferably 20 mass% or less, 15 mass% or less, 13 mass% or less, 10 mass% or less, or 9 mass% or less.

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).

[ solution 78]

The compound represented by the general formula (L-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).

[ solution 79]

The compound represented by the general formula (L-6) is the following compound.

[ solution 80]

(in the formula, R^L61And R^L62Each independently represents R in the general formula (L)^L1And R^L2Same meaning as X^L61And X^L62Each independently represents a hydrogen atom or a fluorine atom. )

R^L61And R^L62Preferably, each independently is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably X^L61And X^L62One of which is a fluorine atom and the other is a hydrogen atom.

The compounds represented by the general formula (L-6) may be used alone or in combination of two or more. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, in one embodiment, the kinds of the compounds used are one, two, three, four, five or more.

The lower limit of the preferable content of the compound represented by formula (L-6) relative to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 14 mass% or more, 16 mass% or more, 20 mass% or more, 23 mass% or more, 26 mass% or more, 30 mass% or more, 35 mass% or more, or 40 mass% or more.

In the case where the emphasis is placed on increasing Δ n, the content is preferably increased, and in the case where the emphasis is placed on precipitation at a low temperature, the content is preferably decreased.

The compound represented by the general formula (L-6) is preferably a compound represented by the formulae (L-6.1) to (L-6.9).

[ solution 81]

The kind of the combinable compound is not particularly limited, but preferably contains one to three kinds, and further preferably contains one to four kinds from these compounds. Further, since the molecular weight distribution of the selected compound is broad also effective in terms of solubility, it is preferable to select one compound from the compounds represented by the formula (L-6.1) or (L-6.2), one compound from the compounds represented by the formula (L-6.4) or (L-6.5), one compound from the compounds represented by the formula (L-6.6) or (L-6.7), one compound from the compounds represented by the formula (L-6.8) or (L-6.9), and suitably combine them. Among them, preferred are compounds represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9).

Further, the compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formula (L-6.10) to the formula (L-6.17), and more preferably a compound represented by the formula (L-6.11).

[ solution 82]

The compound represented by the general formula (L-7) is the following compound.

[ solution 83]

(in the formula, R^L71And R^L72Each independently represents R in the general formula (L)^L1And R^L2Same meaning as A^L71And A^L72Each independently represents a group represented by the general formula (L)^L2And A^L3Same meaning, except that A^L71And A^L72Each hydrogen atom in (A) may independently be substituted by a fluorine atom, Z^L71Is represented by Z in the general formula (L)^L2Same meaning as X^L71And X^L72Each independently represents a fluorine atom or a hydrogen atom. )

In the formula, R^L71And R^L72Preferably independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, A^L71And A^L72Preferably each independently of the other 1, 4-cyclohexylene or 1, 4-phenylene, A^L71And A^L72Each hydrogen atom in (A) may independently be substituted by a fluorine atom, Z^L71Preferably a single bond or COO-, preferably a single bond, X^L71And X^L72Preferably a hydrogen atom.

The type of the combinable compound is not particularly limited, and is combined according to required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. For example, as an embodiment, the kinds of the compounds used are one, two, three, and four.

The amount of the compound represented by the general formula (L-7) contained in the liquid crystal composition is desirably adjusted depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-7) relative to the total amount of the liquid crystal composition is 1 mass% or more, 2 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, 10 mass% or more, 14 mass% or more, 16 mass% or more, or 20 mass% or more.

On the other hand, the upper limit of the content is preferably 30% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass or less, 10% by mass or less, or 5% by mass or less.

When the liquid crystal composition is desired to have a high Tni, the content of the compound represented by the formula (L-7) is preferably slightly high, and when the liquid crystal composition is desired to have a low viscosity, the content is preferably slightly low.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), more preferably a compound represented by the formula (L-7.2).

[ solution 84]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), more preferably a compound represented by the formula (L-7.11).

[ solution 85]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.21) to (L-7.23), more preferably a compound represented by the formula (L-7.21).

[ solution 86]

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

[ solution 87]

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

[ solution 88]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.51) to (L-7.53).

[ solution 89]

The liquid crystal composition of the present invention may further contain a polymerizable compound. The polymerizable compound includes various compounds, and preferably includes at least one compound represented by the following general formula (P).

[ solution 90]

In the formula (P), Z^p1Represents a fluorine atom, a cyano group, a hydrogen atomAn alkyl group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms which may be substituted with a halogen atom, or-Sp^p2-R^p2。

R^p1And R^p2Each represents any one of the following formulae (R-I) to (R-IX).

[ solution 91]

(in the formula, wherein,

at 1 and Sp^p1Or Sp^p2The connection is carried out by connecting the two parts,

R²～R⁶each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms,

w represents a single bond, -O-or methylene,

t represents a single bond or-COO-,

p, t and q each independently represent 0, 1 or 2. )

Sp^p1And Sp^p2Each of which represents a spacer group,

L^p1and L^p2Each independently represents a single bond, -O-, -S-, -CH₂-、-OCH₂-、-CH₂O-、-CO-、-C₂H₄-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CO-NR^a-、-NR^a-CO-、-SCH₂-、-CH₂S-、-CH＝CR^a-COO-、-CH＝CR^a-OCO-、-COO-CR^a＝CH-、-OCO-CR^a＝CH-、-COO-CR^a＝CH-COO-、-COO-CR^a＝CH-OCO-、-OCO-CR^a＝CH-COO-、-OCO-CR^a＝CH-OCO-、-(CH₂)_z-C(＝O)-O-、-(CH₂)_z-O-(C＝O)-、-O-(C＝O)-(CH₂)_z-、-(C＝O)-O-(CH₂)_z-、-CH₂(CH₃)C-C(＝O)-O-、-CH₂(CH₃)C-O-(C＝O)-、-O-(C＝O)-C(CH₃)CH₂、-(C＝O)-O-C(CH₃)-CH₂、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C ≡ C- (wherein, in the formula, R is^aEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4).

M^p2Represents 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, indan-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 1, 3-dioxane-2, 5-diyl or a single bond, M^p2Unsubstituted or optionally substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or-R^p1And (4) substitution.

M^p1Represents any one of the following formulae (i-11) to (ix-11).

[ solution 92]

(wherein, in the formula, in^p1Is connected between^p1、L^p2Or Z^p1And (4) connecting. )

M^p3Represents any one of the following formulae (i-13) to (ix-13).

[ solution 93]

(wherein in the formulae^p1Is connected between^p2Connecting)

m^p2～m^p4Each independently represents 0, 1,2 or 3,

m^p1and m^p5Each independently represents 1,2 or 3,

at Z^p1When a plurality of them are present, they may be the same or different from each other, and R is^p1When a plurality of them are present, they may be the same or different from each other, and R is^p2When a plurality of them are present, they may be the same or different from each other, and are represented by Sp^p1When a plurality of them are present, they may be the same or different from each other, and are represented by Sp^p2When a plurality of them exist, they may be the same or different from each other, and L is^p1When plural, they may be the same or different from each other, in M^p2When a plurality of the compounds exist, they may be the same as or different from each other.

The liquid crystal composition can suitably form a pretilt angle of liquid crystal molecules by further containing a polymerizable compound in addition to the alignment auxiliary (the first compound and the second compound).

The liquid crystal composition preferably does not contain a compound having a structure in which oxygen atoms are linked to each other, such as a peracid (-CO-OO-) structure, in the molecule.

When importance is attached to the reliability and long-term stability of the liquid crystal composition, the content of the compound having a carbonyl group with respect to the total amount of the liquid crystal composition is preferably 5% by mass or less, more preferably 3% by mass or less, still more preferably 1% by mass or less, and most preferably substantially none.

When importance is attached to the stability by UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% by mass or less, more preferably 10% by mass or less, further preferably 8% by mass or less, further preferably 5% by mass or less, particularly preferably 3% by mass or less, and most preferably substantially none, relative to the total amount of the liquid crystal composition.

The content of the compound having 6-membered ring structures in the molecule is preferably increased, and the content of the compound having 6-membered ring structures in the molecule is preferably 80% by mass or more, more preferably 90% by mass or more, further preferably 95% by mass or more, and most preferably substantially 100% by mass, based on the total amount of the liquid crystal composition.

In order to suppress deterioration due to oxidation of the liquid crystal composition, the content of the compound having a cyclohexenylene group as a ring structure is preferably reduced, and the content of the compound having a cyclohexenylene group relative to the total amount of the liquid crystal composition is preferably 10% by mass or less, more preferably 8% by mass or less, still more preferably 5% by mass or less, particularly preferably 3% by mass or less, and most preferably substantially none.

When importance is attached to the improvement of viscosity and the improvement of Tni, it is preferable that the content of the 2-methylbenzene-1, 4-diyl compound having a hydrogen atom in the molecule which may be substituted with a halogen atom is reduced, and the content of the compound having the 2-methylbenzene-1, 4-diyl compound in the molecule is preferably 10% by mass or less, more preferably 8% by mass or less, further preferably 5% by mass or less, particularly preferably 3% by mass or less, and most preferably substantially none, relative to the total amount of the liquid crystal composition.

In the present specification, the term "compound X" is not substantially contained in the liquid crystal composition means that the "compound X" is contained in an amount not exceeding the amount unintentionally (inevitably) contained in the liquid crystal composition.

Average elastic constant (K) of liquid crystal composition_AVG) The lower limit of (b) is preferably 10 or more, 10.5 or more, 11 or more, 11.5 or more, 12 or more, 12.3 or more, 12.5 or more, 12.8 or more, 13 or more, 13.3 or more, 13.5 or more, 13.8 or more, 14 or more, 14.3 or more, 14.5 or more, 14.8 or more, 15 or more, 15.3 or more, 15.5 or more, 15.8 or more, 16 or more, 16.3 or more, 16.5 or more, 16.8 or more, 17 or more, 17.3 or more, 17.5 or more, 17.8 or more, or 18 or more.

On the other hand, the average elastic constant (K) of the liquid crystal composition_AVG) Has a preferable upper limit value of 25 or less, 24.5 or less, 24 or less, 23.5 or less, 23 or less, 22.8 or less, 22.5 or less, 22.3 or less, 22 or less, 21.8 or less, 21.5 or less, 21.3 or less, 21 or less, 20.8 or less, 20.5 or less, 20.3 or less, 20 or less, 19.8 or less, 19.5 or less, 19.3 or less, 19 or less, 18.8 or less, 18.5 or less, 18.3 or less, 18 or less, 17.8 or less, 17.5 or less, 17.3 or less, or more,17 or less.

In the case where reduction of power consumption is important, it is effective to suppress the amount of backlight light, and since the liquid crystal display element preferably has a high light transmittance, K is preferably used_AVGIs set slightly lower. In the case where importance is attached to improvement of response speed, it is preferable to set K to_AVGThe value of (c) is set slightly higher.

(liquid Crystal display element)

The liquid crystal composition of the invention can be applied to liquid crystal display elements. Hereinafter, an example of the liquid crystal display device according to the present embodiment will be described with reference to fig. 1 and 2 as appropriate.

Fig. 1 is a diagram schematically showing the structure of a liquid crystal display element. Fig. 1 shows the respective components separated from each other for the sake of convenience of explanation.

As shown in fig. 1, a liquid crystal display element 1 according to the present embodiment includes: a first substrate 2 and a second substrate 3 disposed so as to face each other, and a liquid crystal layer 4 provided between the first substrate 2 and the second substrate 3, wherein the liquid crystal layer 4 contains the liquid crystal composition.

A pixel electrode layer 5 is formed on the first substrate 2 on the liquid crystal layer 4 side. A common electrode layer 6 is formed on the second substrate 3 on the liquid crystal layer 4 side. The first substrate 2 and the second substrate 3 may be sandwiched by a pair of polarizing plates 7 and 8. A color filter 9 may be further provided on the liquid crystal layer 4 side of the second substrate 3.

That is, the liquid crystal display element 1 according to one embodiment has a structure in which a first polarizing plate 7, a first substrate 2, a pixel electrode layer 5, a liquid crystal layer 4 containing a liquid crystal composition, a common electrode layer 6, a color filter 9, a second substrate 3, and a second polarizing plate 8 are sequentially stacked.

The first substrate 2 and the second substrate 3 are formed of a material having flexibility, such as glass or plastic. At least one of the first substrate 2 and the second substrate 3 is formed of a transparent material, and the other is formed of a transparent material, or an opaque material such as metal or silicon.

The first substrate 2 and the second substrate 3 are bonded to each other with a sealing material and a sealing material such as an epoxy thermosetting composition disposed in the peripheral region, and for the purpose of maintaining the distance between the substrates, for example, a granular spacer such as glass particles, plastic particles, or alumina particles, or a spacer formed by photolithography and containing a resin may be disposed therebetween.

The first polarizing plate 7 and the second polarizing plate 8 can adjust the polarizing axes of the respective polarizing plates so that the viewing angle and the contrast are improved, and preferably have parallel transmission axes so that the transmission axes operate in a normally black mode. In particular, it is preferable that either one of the first polarizing plate 7 and the second polarizing plate 8 is arranged so as to have a transmission axis parallel to the alignment direction of the liquid crystal molecules when no voltage is applied.

From the viewpoint of preventing light leakage, the color filter 9 is preferably formed into a black matrix, and a black matrix (not shown) is preferably formed in a portion corresponding to the thin film transistor.

The black matrix may be provided on the substrate on the opposite side of the array substrate together with the color filter, may be provided on the array substrate side together with the color filter, or may be separately provided on the array substrate and the color filter on the other substrate. The black matrix may be provided separately from the color filters, but the transmittance may be decreased by overlapping the colors of the color filters.

Fig. 2 is an enlarged plan view of a region surrounded by an I-line in fig. 1 as a part of the pixel electrode layer 5 formed on the first substrate 2.

As shown in fig. 2, in the pixel electrode layer 5 including thin film transistors formed on the surface of the first substrate 2, a plurality of gate bus lines 11 for supplying scanning signals and a plurality of data bus lines 12 for supplying display signals are arranged in a matrix shape so as to intersect with each other. Fig. 2 shows only a pair of gate bus lines 11 and a pair of

data bus lines

12 and 12.

A unit pixel of the liquid crystal display element is formed by a region surrounded by the plurality of gate bus lines 11 and the plurality of data bus lines 12, and a pixel electrode 13 is formed in the unit pixel. The pixel electrode 13 has a so-called fishbone structure having two trunk portions that are orthogonal to each other and form a cross shape, and a plurality of branch portions extending from the trunk portions.

Further, a Cs electrode 14 is provided between the pair of

gate bus lines

11, 11 substantially in parallel with the gate bus lines 11. In addition, a thin film transistor including a source electrode 15 and a drain electrode 16 is provided in the vicinity of an intersection where the gate bus line 11 and the data bus line 12 intersect with each other. The drain electrode 16 is provided with a contact hole 17.

The gate bus lines 11 and the data bus lines 12 are preferably formed of a metal film, more preferably of Al, Cu, Au, Ag, Cr, Ta, Ti, Mo, W, Ni, or an alloy thereof, and still more preferably of Mo, Al, or an alloy thereof.

The pixel electrode 13 is preferably a transparent electrode in order to increase the transmittance. The transparent electrode can be formed by sputtering an Oxide semiconductor (ZnO, InGaZnO, SiGe, GaAs, Indium Zinc Oxide (IZO), Indium Tin Oxide (ITO), SnO, TiO, AZTO (AlZnSnO), or the like).

In this case, the thickness of the transparent electrode may be 10nm to 200 nm. In order to reduce the resistance, the transparent electrode may be formed by firing an amorphous ITO film to form a polycrystalline ITO film.

In the liquid crystal display device of the present embodiment, for example, a metal material such as Al or an alloy thereof is sputtered on the first substrate 2 and the second substrate 3 to form wirings, and the pixel electrode layer 5 and the common electrode layer 6 are formed separately. The color filter 9 can be produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like.

In the case of a method of manufacturing a color filter by a pigment dispersion method, a curable color composition for a color filter is applied to the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. This step is performed for each of the three colors of red, green, and blue, whereby a pixel portion for a color filter can be manufactured. The color filter 9 may be provided on the substrate side having the TFT or the like.

The first substrate 2 and the second substrate 3 are opposed to each other so that the pixel electrode layer 5 and the common electrode layer 6 are located inside, but in this case, the distance between the first substrate 2 and the second substrate 3 may be adjusted by a spacer. In this case, the thickness of the liquid crystal layer 4 is preferably adjusted to be, for example, 1 μm to 100 μm.

When the polarizing plate 7 or the polarizing plate 8 is used, the product of the refractive index anisotropy Δ n of the liquid crystal layer 4 and the thickness of the liquid crystal layer 4 is preferably adjusted so that the contrast becomes maximum. In the case where there are two polarizing plates 7 and 8, the polarizing axes of the respective polarizing plates may be adjusted so that the viewing angle and the contrast are improved. Further, a retardation film for widening a viewing angle may be used. Then, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates so as to provide a liquid crystal injection port, the substrates are bonded to each other, and the sealant is thermally cured by heating.

The method of sandwiching the composition between the two substrates 2 and 3 may be a general vacuum infusion method or a Drop infusion (ODF: One Drop Fill) method, and the vacuum infusion method has a problem that no Drop mark is generated but an infusion mark remains, and the present embodiment can be preferably used for a display element manufactured by the ODF method.

In the liquid crystal display element production step of the ODF method, an epoxy-based photo-thermal curable sealant or the like is drawn into a closed-loop bank shape on one of the back plate and the front plate by using a dispenser, and a predetermined amount of the composition is dropped into the closed-loop bank shape under deaeration, and then the front plate and the back plate are joined to each other, whereby a liquid crystal display element can be produced.

In this embodiment mode, the ODF method can suppress the occurrence of dropping marks when the liquid crystal composition is dropped onto the substrate. The term "drop mark" is defined as a phenomenon in which white appears on the trace of a liquid crystal composition when black display is performed.

In addition, in the manufacturing process of the liquid crystal display element by the ODF method, it is necessary to drop the most preferable liquid crystal injection amount depending on the size of the liquid crystal display element, but the liquid crystal composition of the present embodiment has little influence of a sudden pressure change or impact in the dropping device when dropping the liquid crystal, and the dropping of the liquid crystal can be continued stably for a long period of time, and therefore the yield of the liquid crystal display element can be kept high.

In particular, in small liquid crystal display elements which are used in large numbers in smart phones which are popular in recent years, it is difficult to control the deviation from the optimum value within a certain range because the optimum liquid crystal injection amount is small.

When the first compound and the second compound each contain a polymerizable group and the liquid crystal composition contains a polymerizable compound, a method of polymerizing these compounds is preferably a method of polymerizing the compounds by irradiating active energy rays such as ultraviolet rays or electron beams singly or in combination or sequentially because an appropriate polymerization rate is desired in order to obtain good alignment properties of liquid crystal molecules. In the case of using ultraviolet rays, a polarized light source may be used, and a non-polarized light source may be used.

In addition, when polymerizing a liquid crystal composition in a state of being sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency to the active energy ray. In addition, the following method may also be used: in the case of light irradiation, only a specific portion is polymerized using a mask, and then the orientation state of the unpolymerized portion is changed by changing the conditions such as an electric field, a magnetic field, or temperature, and further, the polymerization is performed by irradiation with an active energy ray.

In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating-current electric field to the liquid crystal composition. The applied alternating electric field is preferably alternating at a frequency of 10Hz to 10kHz, more preferably at a frequency of 60Hz to 10kHz, the voltage being selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled using the applied voltage. In a liquid crystal display element of a transverse electric field type MVA (multi-domain vertical alignment) mode, it is preferable to control the pretilt angle to 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.

The temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the liquid crystal composition can be maintained. The liquid crystal composition is preferably polymerized at a temperature close to room temperature, that is, typically at a temperature of 15 to 35 ℃.

As the lamp for generating ultraviolet rays, a metal halide lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, or the like can be used. As the wavelength of the ultraviolet rays to be irradiated, ultraviolet rays having a wavelength region not within the absorption wavelength region of the liquid crystal composition are preferably irradiated, and the ultraviolet rays are preferably used by being filtered as necessary.

The intensity of the ultraviolet ray to be irradiated is preferably 0.1mW/cm²～100W/cm²More preferably 2mW/cm²～50W/cm². The amount of energy of the ultraviolet rays to be irradiated can be suitably adjusted, and is preferably 10mJ/cm²～500J/cm²More preferably 100mJ/cm²～200J/cm². The intensity may be changed when ultraviolet rays are irradiated.

The time for irradiating ultraviolet rays may be appropriately selected depending on the intensity of ultraviolet rays to be irradiated, and is preferably 10 seconds to 3600 seconds, and more preferably 10 seconds to 600 seconds.

In the liquid crystal composition of the present invention, since the alignment aid (the first compound and the second compound) does not inhibit the polymerization reaction of the polymerizable compound, the polymerizable compounds are polymerized appropriately, and the unreacted polymerizable compound can be prevented from remaining in the liquid crystal composition.

For example, in the case of using the compound represented by the general formula (P) as the polymerizable compound, the obtained liquid crystal display element 1 includes: two substrates 2 and 3, and a liquid crystal layer 4 provided between the two substrates 2 and 3 and containing a first compound, a second compound, and a polymer of a compound represented by general formula (P). In this case, it is considered that the first compound, the second compound, and the polymer of the compound represented by the general formula (P) are present in the liquid crystal layer 4 on the substrates 2 and 3 side in an offset manner.

When the polymerizable compound is not used, the liquid crystal layer 4 includes a polymer of the first compound and the second compound.

The liquid crystal display element 1 may be an active matrix driving liquid crystal display element. The liquid crystal display element 1 may be a PSA type, PSVA type, VA type, IPS (In-Plane Switching) type, FFS (Fringe Field Switching) type, or ECB (electrically controlled birefringence) type liquid crystal display element, and is preferably a PSA type liquid crystal display element.

In the liquid crystal display element of the present embodiment, since the liquid crystal composition containing the alignment auxiliary (the first compound and the second compound) is used, it is not necessary to provide an alignment film such as a polyimide alignment film on the liquid crystal layer 4 side of the first substrate 2 and the second substrate 3. That is, the liquid crystal display element of the present embodiment may be configured such that at least one of the two substrates does not have an alignment film such as a polyimide alignment film.

The alignment aid, the liquid crystal composition, and the liquid crystal display element of the present invention have been described above based on the illustrated embodiments, but the present invention is not limited thereto, and each configuration may be replaced with any configuration having the same function, and any other configuration may be added.

Examples

Hereinafter, examples of the present invention will be described, but the present invention is not limited to the following examples.

The properties measured in the examples are as follows.

T_ni: nematic phase-isotropic liquid phase transition temperature (. degree.C.)

Δ n: refractive index anisotropy at 20 DEG C

eta.viscosity at 20 ℃ (mPa. multidot.s)

γ 1: rotational tack at 20 ℃ (mPa. multidot.s)

Δ ε: anisotropy of dielectric constant at 20 DEG C

K₃₃: elastic constant K at 20 DEG C₃₃(pN)

1. Preparation of liquid-crystalline mixtures

Hereinafter, the following abbreviations are used to describe the compounds.

< Ring Structure >

[ solution 94]

< side chain Structure >

[ Table 1]

Shorthand writing	Chemical structure
		-n	-C_nH_2n+1
n-	C_nH_2n+1-
		-On	-OC_nH_2n+1
nO-	C_nH_2n+1O-
		-V	-CH＝CH₂
V-	CH₂＝CH-
		-V1	-CH＝CH-CH₃
1V-	CH₃-CH＝CH-
		-2V	-CH₂-CH₂-CH＝CH₂
V2-	CH₂＝CH-CH₂-CH₂-
		-2V1	-CH₂-CH₂-CH＝CH-CH₃
1V2-	CH₃-CH＝CH-CH₂-CH₂-

(wherein n in the table is a natural number.)

< connection Structure >

[ Table 2]

Shorthand writing	Chemical structure
		-n-	-C_nH_2n-
-nO-	-C_nH_2nO-
		-On-	-OC_nH_2n-
-COO-	-C(＝O)-O-
		-OCO-	-O-C(＝O)-
-V-	-CH＝CH-
		-nV-	-C_nH_2n-CH＝CH-
-Vn-	-CH＝CH-C_nH_2n-
		-T-	-C≡C-
-CF2O-	-CF₂-O-
		-OCF2-	-O-CF₂-

(wherein n in the table is a natural number.)

(liquid Crystal mixture LC-1)

First, a mixture HLC-1 of the formulation shown in table 3 below was prepared. To this mixture HLC-1100 wt% was added 0.3 wt% of the following polymerizable compound (R-1-0), and dissolved by heating, thereby obtaining a liquid crystal mixture LC-1.

[ Table 3]

[ solution 95]

(liquid Crystal mixture LC-2. liquid Crystal mixture LC-8)

First, mixtures HLC-2 to HLC-8 of the formulations shown in table 4 below were prepared. To 100% by weight of each of these mixture HLC-2 to mixture HLC-8, 0.3% by weight of the above polymerizable compound (R-1-0) was added and dissolved by heating, thereby obtaining liquid crystal mixtures LC-2 to LC-8.

[ Table 4]

(liquid Crystal mixture LC-9. liquid Crystal mixture LC-16)

To 100% by weight of each of the mixtures HLC-1 to HLC-8, 0.3% by weight of the polymerizable compound (R-1-0) and 0.5% by weight of the following polymerizable compound (R-1-1) were added and dissolved by heating, thereby obtaining liquid crystal mixtures LC-9 to LC-16.

[ solution 96]

2. Preparation of liquid Crystal composition

(example 1)

A liquid crystal composition was prepared by adding 0.3% by weight of the compound (PJ-I-1) as the first compound and 0.3% by weight of the compound (PJ-II-1) as the second compound to the liquid crystal mixture LC-1100% by weight.

(example 2)

A liquid crystal composition was prepared by adding 0.5% by weight of the compound (PJ-I-1) and 0.5% by weight of the compound (PJ-II-1) to the liquid crystal mixture LC-1100% by weight.

(example 3)

A liquid crystal composition was prepared by adding 0.5% by weight of the compound (PJ-I-1) and 1.0% by weight of the compound (PJ-II-1) to the liquid crystal mixture LC-1100% by weight.

(examples 4 to 6)

Liquid crystal compositions were prepared in the same manner as in examples 1 to 3, except that the first compound was changed from compound (PJ-I-1) to compound (PJ-I-2).

(examples 7 to 9)

Liquid crystal compositions were prepared in the same manner as in examples 1 to 3, except that the first compound was changed from compound (PJ-I-1) to compound (PJ-I-3).

(examples 10 to 12)

Liquid crystal compositions were prepared in the same manner as in examples 1 to 3, except that the first compound was changed from compound (PJ-I-1) to compound (PJ-I-4).

(examples 13 to 15)

Liquid crystal compositions were prepared in the same manner as in examples 1 to 3, except that the first compound was changed from compound (PJ-I-1) to compound (PJ-I-5).

(examples 16 to 18)

Liquid crystal compositions were prepared in the same manner as in examples 7 to 9, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-2).

(example 19 to example 21)

Liquid crystal compositions were prepared in the same manner as in examples 7 to 9, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-3).

(examples 22 to 24)

Liquid crystal compositions were prepared in the same manner as in examples 7 to 9, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-4).

(example 25 to example 27)

Liquid crystal compositions were prepared in the same manner as in examples 4 to 6, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-2).

(examples 28 to 30)

Liquid crystal compositions were prepared in the same manner as in examples 4 to 6, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-3).

(example 31 to example 33)

Liquid crystal compositions were prepared in the same manner as in examples 4 to 6, except that the second compound was changed from compound (PJ-II-1) to compound (PJ-II-4).

(example 34 to example 43)

A liquid crystal composition was prepared in the same manner as in example 23, except that the liquid crystal mixture LC-1 was changed to the liquid crystal mixtures LC-2 to LC-8.

Comparative example 1

A liquid crystal composition was prepared in the same manner as in example 1 except that the compound (PJ-I-1) and the compound (PJ-II-1) were not used.

Comparative examples 2 to 4

Liquid crystal compositions were prepared in the same manner as in example 1, except that 1.0 wt% of each of the following compounds Ref-1 to Ref-3 was added to the liquid crystal mixture LC-1100 wt%.

[ solution 97]

Comparative examples 5 to 13

A liquid crystal composition was prepared in the same manner as in example 1 except that 1.0 wt% of each of the compounds (PJ-I-1) to (PJ-I-5) and (PJ-II-1) to (PJ-II-4) was added to the liquid crystal mixture LC-1100 wt%.

Comparative examples 14 to 20

A liquid crystal composition was prepared in the same manner as in example 1, except that 1.0 wt% of the above-mentioned compound (PJ-I-3) was added to each 100 wt% of the liquid crystal mixtures LC-1 to LC-8.

3. Evaluation of

The following evaluation tests were carried out on each of the liquid crystal compositions of examples and comparative examples.

3-1 evaluation test of Low temperature stability

The liquid crystal composition was filtered with a membrane filter (PTFE 13mm to 0.2 μm, manufactured by Agilent Technologies) and allowed to stand under vacuum and reduced pressure for 15 minutes to remove dissolved air. It was washed with acetone and 0.5g was weighed in a well-dried glass bottle and allowed to stand at a low temperature of-25 ℃ for 14 days. Thereafter, the presence or absence of precipitation was visually observed, and the following 4 stages were performed to determine the presence or absence of precipitation.

A: precipitation was not confirmed after leaving for 14 days.

B: precipitation was confirmed after standing for 7 days.

C: precipitation was confirmed after leaving for 3 days.

D: precipitation was confirmed after standing for 1 day.

3-2 evaluation test of vertical alignment Property 1

First, a first substrate (common electrode substrate) having a transparent common electrode layer but not having an alignment film and a second substrate (pixel electrode substrate) having a pixel electrode layer including a transparent pixel electrode driven by an active element but not having an alignment film are prepared. Next, a sealant is disposed along the outer peripheral portion of the first substrate, and a liquid crystal composition is dropped on the first substrate and inside the sealant.

Then, the liquid crystal composition is sandwiched between the first substrate and the second substrate by disposing the second substrate and the first substrate to face each other with the sealant interposed therebetween. In this state, the sealing material was cured under the conditions of normal pressure, 110 ℃ and 2 hours. A liquid crystal cell having a cell gap of 3.2 μm was thus obtained.

The vertical alignment property and the alignment unevenness such as drop marks were observed using a polarizing microscope, and evaluated in the following 4 stages.

A: including the end parts, are uniformly vertically oriented over the entire surface

B: with few orientation defects but at tolerable levels

C: many defects in orientation including end portions are unacceptable

D: poor orientation is rather poor

3-3 evaluation test of vertical orientation 2

First, a first substrate (filter substrate) having a color filter layer but no alignment film and a second substrate (pixel electrode substrate) having a pixel electrode layer including a transparent pixel electrode driven by an active element but no alignment film are manufactured. Next, a sealant is disposed along the outer peripheral portion of the first substrate, and a liquid crystal composition is dropped on the first substrate and inside the sealant.

B: with few orientation defects but at tolerable levels

C: many defects in orientation including end portions are unacceptable

D: poor orientation is rather poor

3-4 evaluation test of vertical alignment 3

First, a first substrate (electrode filter substrate) including both a transparent common electrode layer portion and a color filter layer portion having patterned surfaces and having no alignment film, and a second substrate (pixel electrode substrate) including a transparent pixel electrode portion and a pixel electrode layer driven by an active element and a partial color filter layer portion and having no alignment film are manufactured. Next, a sealant is disposed along the outer peripheral portion of the first substrate, and a liquid crystal composition is dropped on the first substrate and inside the sealant.

Then, the liquid crystal composition is sandwiched between the first substrate and the second substrate by disposing the second substrate and the first substrate to face each other with the sealant interposed therebetween. In this state, the sealant was cured under normal pressure, 110 ℃ and 2 hours, thereby obtaining a liquid crystal cell having a cell gap of 3.5 μm.

A: including the boundary part and end part of the pattern substrate, and is uniformly vertically oriented on the whole surface

B: with few orientation defects but at tolerable levels

C: many defects in orientation including end portions are unacceptable

D: poor orientation is rather poor

3-5 evaluation test of Pre-Tilt Angle formation

The liquid crystal cell used in the above-mentioned "3-2. evaluation test of vertical alignment 1" was irradiated with a high-pressure mercury lamp for 200 seconds while applying a rectangular alternating current of 10V and 100Hz and an illuminance at 365nm of 100m/cm²UV light of (1). Thereafter, a rectangular ac wave of 10V and 100Hz was applied while applying a physical external force to the cell, and the stability of white display was observed in a cross nicol state, and evaluated in the following 4 stages.

B: with few orientation defects but at tolerable levels

C: many defects in orientation including end portions are unacceptable

D: poor orientation is rather poor

3-6 evaluation test of residual monomer amount

For the cell used in the "evaluation test of 3-5. formation of pretilt Angle", Toshiba Lighting technique (Toshiba Lighting) for further 60 minutes was irradiated&Technology) UV fluorescent lamp (illuminance at 313nm 1.7 mW/cm)²) The residual amount of the polymerizable compound (R1-1-0) after irradiation was quantified by HPLC, and the amount of the residual monomer was determined. According toThe residual amount of the monomer was evaluated in the following 4 stages.

A: less than 300ppm

B: 300ppm or more and less than 500ppm

C: 500ppm or more and less than 1500ppm

D: 1500ppm or more

3-7 evaluation test of response characteristics

For the cell having a cell gap of 3.2 μm used in the "evaluation test of 3-5. formation of pretilt Angle", Toshiba Lighting technique (Toshiba Lighting) was further irradiated for 60 minutes&Technology) UV fluorescent lamp (illuminance at 313nm 1.7 mW/cm)²). The response speed was measured for the thus obtained unit. The response speed was measured by measuring Voff at 6V using DMS703 available from AUTRONIC-MELCHERS under a temperature condition of 25 ℃. The response characteristics were evaluated in the following 4 stages.

A: less than 5ms

B: 5ms or more and less than 15ms

C: 15ms or more and less than 25ms

D: over 25ms

[ Table 5]

[ Table 6]

[ Table 7]

[ Table 8]

[ Table 9]

[ Table 10]

As described above, it is understood that the alignment aid and the liquid crystal composition of the present invention have excellent alignment constraint of liquid crystal molecules and high storage stability. In addition, it is also known that the liquid crystal display element of the present invention has excellent response characteristics.

In addition, similarly to examples 1 to 40 and comparative examples 1 to 20, liquid crystal compositions were obtained by adding various alignment aids to liquid crystal mixtures LC-9 to LC-16 and dissolving them by heating. As a result of evaluating the vertical alignment properties of these liquid crystal compositions in the same manner as described above, it was confirmed that the alignment properties of the examples were more excellent than those of the comparative examples.

Description of the symbols

1: liquid crystal display element

2: first substrate

3: second substrate

4: liquid crystal layer

5: pixel electrode layer

6: common electrode layer

7. 8: polarizing plate

9: color filter

11: gate bus

12: data bus

13: pixel electrode

14: cz electrode

15: source electrode

16: drain electrode

17: contact hole

Claims

1. An alignment assistant which is disposed between two substrates together with liquid crystal molecules and aligns the liquid crystal molecules spontaneously,

the orientation aid contains:

2. The orientation aid according to claim 1, wherein the first compound and the second compound each comprise at least one polymerizable group.

3. The alignment aid according to claim 2, wherein the polymerizable group is selected from the group represented by the following general formulae (P-1) to (P-13),

[ solution 1]

In the formula, the black dot at the right end represents a connecting key.

4. The orientation aid of any one of claims 1 to 3, wherein the first affinity group and the second affinity group each comprise a group selected from the group consisting of:

[ solution 2]

In the formula, black dots represent connecting bonds.

5. The alignment aid according to claim 4, wherein the first affinity group is selected from the group represented by the following general formula (K1-1) to general formula (K1-3):

[ solution 3]

In the formula (I), the compound is shown in the specification,

the black dot at the left end represents a connection key,

W^K2represents methine, C-CH₃、C-C₂H₅A nitrogen atom or a silicon atom,

W^K3represents a carbon atom, and represents a carbon atom,

X₁And X₂At least one of them represents an-OH group,

X₃、X₄and X₅At least one of them represents an-OH group,

Sp₁、Sp₂and Sp₃Each represents a single bond or a spacer;

the second affinity group is selected from the group represented by the following general formula (K2-1) to general formula (K2-14):

[ solution 4]

In the formula (I), the compound is shown in the specification,

the black dot at the left end represents a connection key,

Z^K1represents an oxygen atom or a sulfur atom,

U^K1、V^K1and S^K1Each independently represents a methine group or a nitrogen atom, wherein U^K1Is methine, V^K1Is methine and S^K1Except for the combination of nitrogen atoms, or a combination thereof,

6. The orientation aid of claim 4 or 5, wherein the first affinity group comprises a hydroxyl group and the second affinity group comprises an ether group or a carbonate group.

7. The alignment aid according to any one of claims 2 to 6, wherein the first compound and the second compound each contain a liquid crystal proto-group,

the first affinity group, the second affinity group, and the polymerizable group are each connected to the mesogen directly or via a spacer.

8. The alignment aid according to claim 7, wherein the first compound and the second compound each comprise a terminal group attached to the liquid crystal ortho-group on the opposite side to the first affinity group or the second affinity group.

9. The alignment aid according to claim 8, wherein the terminal group is represented by a C1-40 linear or branched alkyl group, a C1-40 linear or branched halogenated alkyl group, or a polymerizable group bonded to the liquid crystal raw group directly or via a spacer, wherein-CH in the alkyl group or the halogenated alkyl group is₂-may be substituted with-CH ═ CH-, -C ≡ C-, -O-, -NH-, -COO-, or-OCO-, but-O-is not continuous.

10. The alignment aid according to any one of claims 5, 7 to 9, wherein the spacer is-CH ═ CH-, -CF ═ CF-, -C ≡ C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF₂O-、-OCF₂-、-CH＝CHCOO-、-OCOCH＝CH-、-CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-or a linear or branched alkylene group having 1 to 20 carbon atoms, wherein one or two or more-CH groups which are not adjacent to each other in the alkylene group₂-may be substituted by-O-, -COO-or-OCO-.

11. The alignment aid according to any one of claims 7 to 10, wherein the mesogen is represented by the following general formula (i):

[ solution 5]

In the formula (I), the compound is shown in the specification,

black dots at the left end and black dots at the right end represent connection keys,

Zⁱ¹represents a single bond, -CH-, -CF-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF₂O-、-OCF₂-、-CH＝CHCOO-、-OCOCH＝CH-、-CH₂-CH₂COO-、-OCOCH₂-CH₂-、-CH＝C(CH₃)COO-、-OCOC(CH₃)＝CH-、-CH₂-CH(CH₃)COO-、-OCOCH(CH₃)-CH₂-、-OCH₂CH₂O-or alkylene having 2 to 20 carbon atoms, wherein one or two or more-CH groups not adjacent to each other in the alkylene group₂May be taken via-O-, -COO-or-OCO-Instead of the first generation,

mⁱ¹represents an integer of 1 to 5, and a salt thereof,

12. A liquid crystal composition comprising the alignment aid according to any one of claims 1 to 11 and liquid crystal molecules, wherein the liquid crystal composition has a negative dielectric anisotropy Δ ∈.

13. The liquid crystal composition according to claim 12, wherein the liquid crystal molecule comprises a compound selected from the group represented by the following general formulae (N-1) to (N-3):

[ solution 6]

In the formula (I), the compound is shown in the specification,

R^N11、R^N12、R^N21、R^N22、R^N31and R^N32Each independently represents an alkyl group having 1 to 8 carbon atoms, wherein one or two or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

A^N11、A^N12、A^N21、A^N22、A^N31and A^N32Each independently represents a group selected from the group consisting of the following group (a), group (b), group (c) and group (d):

(a)1, 4-cyclohexylene radical, in which one-CH group is present in the radical₂-or two or more-CH's which are not contiguous₂-may be substituted by-O-,

(b)1, 4-phenylene in which one or more than two noncontiguous-CH groups present in the group may be substituted by-N ═ or,

(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, wherein one or two or more of-CH ═ which are not adjacent and are present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by — N ═ and

(d) a 1, 4-cyclohexenylene group,

the group (a), the group (b), the group (c) and the group (d) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,

Z^N11、Z^N12、Z^N21、Z^N22、Z^N31and Z^N32Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

X^N21represents a hydrogen atom or a fluorine atom,

T^N31represents-CH₂-or an oxygen atom,

n^N11、n^N12、n^N21、n^N22、n^N31and n^N32Each independently represents an integer of 0 to 3, and n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Independently of one another is 1,2 or 3,

14. The liquid crystal composition according to claim 12 or 13, wherein the liquid crystal molecule comprises a compound represented by the following general formula (L):

[ solution 7]

In the formula (I), the compound is shown in the specification,

R^L1and R^L2Each independently represents an alkyl group having 1 to 8 carbon atoms, wherein one or two or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be represented by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OThe substitution of CO < - >, and the substitution of the organic solvent,

n^L1represents 0, 1,2 or 3,

A^L1、A^L2and A^L3Each independently represents a group selected from the group consisting of the following group (a), group (b) and group (c):

(b)1, 4-phenylene in which one or more-CH-groups present in the radical may be substituted by-N-and

(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, wherein one or two or more-CH ═ s which are not adjacent and are present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ s,

the group (a), the group (b) and the group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,

15. The liquid crystal composition according to any one of claims 12 to 14, further comprising a polymerizable compound.

16. The liquid crystal composition according to claim 15, wherein the polymerizable compound comprises at least one of compounds represented by the following general formula (P):

[ solution 8]

In the formula (I), the compound is shown in the specification,

Z^p1represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms which may be substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms which may be substituted with a halogen atom, or-Sp^p2-R^p2，

R^p1And R^p2Each represents any one of the following formulae (R-I) to (R-IX):

[ solution 9]

In the formula (I), the compound is shown in the specification,

w represents a single bond, -O-or methylene,

t represents a single bond or-COO-,

p, t and q each independently represent 0, 1 or 2,

Sp^p1and Sp^p2Each of which represents a spacer group,

L^p1and L^p2Each independently represents a single bond, -O-, -S-, -CH₂-、-OCH₂-、-CH₂O-、-CO-、-C₂H₄-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CO-NR^a-、-NR^a-CO-、-SCH₂-、-CH₂S-、-CH＝CR^a-COO-、-CH＝CR^a-OCO-、-COO-CR^a＝CH-、-OCO-CR^a＝CH-、-COO-CR^a＝CH-COO-、-COO-CR^a＝CH-OCO-、-OCO-CR^a＝CH-COO-、-OCO-CR^a＝CH-OCO-、-(CH₂)_z-C(＝O)-O-、-(CH₂)_z-O-(C＝O)-、-O-(C＝O)-(CH₂)_z-、-(C＝O)-O-(CH₂)_z-、-CH₂(CH₃)C-C(＝O)-O-、-CH₂(CH₃)C-O-(C＝O)-、-O-(C＝O)-C(CH₃)CH₂、-(C＝O)-O-C(CH₃)-CH₂、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C-, wherein, in the formula, R^aEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, z represents an integer of 1 to 4,

M^p2represents 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, indan-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 1, 3-dioxane-2, 5-diyl or a single bond, M^p2Unsubstituted or optionally substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or-R^p1The substitution is carried out by the following steps,

M^p1represents any one of the following formulae (i-11) to (ix-11):

[ solution 10]

In the formula, in^p1Is connected between^p1、L^p2Or Z^p1The connection is carried out by connecting the two parts,

M^p3represents any one of the following formulae (i-13) to (ix-13):

[ solution 11]

In the formula, in^p1Is connected between^p2The connection is carried out by connecting the two parts,

m^p2～m^p4each independently represents 0, 1,2 or 3,

m^p1and m^p5Each independently represents 1,2 or 3,

17. A liquid crystal display element, comprising: two substrates, and a liquid crystal layer comprising the liquid crystal composition according to any one of claims 12 to 16 disposed between the two substrates.

18. The liquid crystal display element according to claim 17, wherein the liquid crystal layer comprises a polymer of the first compound and the second compound.

19. The liquid crystal display element according to claim 17 or 18, which is used for active matrix driving.

20. The liquid crystal display element according to any one of claims 17 to 19, which is of a PSA type, a PSVA type, a VA type, an IPS type, an FFS type, or an ECB type.

21. The liquid crystal display element according to any one of claims 17 to 20, wherein at least one of the two substrates does not have an alignment film.