CN110872519A

CN110872519A - Liquid crystal composition and liquid crystal display element

Info

Publication number: CN110872519A
Application number: CN201910758514.6A
Authority: CN
Inventors: 须藤豪; 栗泽和树
Original assignee: DIC Corp
Current assignee: Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority date: 2018-09-03
Filing date: 2019-08-16
Publication date: 2020-03-10
Also published as: JP7139797B2; JP2020037630A

Abstract

The invention provides a liquid crystal composition and a liquid crystal display element. The present invention addresses the problem of providing a polymerizable compound-containing liquid crystal composition that can achieve a high polymerization rate, a large tilt angle formation, a high tilt angle stability, and a high Voltage Holding Ratio (VHR) at the same time, and a PSA-type or PSVA-type liquid crystal display element using the same. The present invention solves the above problems by providing a liquid crystal composition containing a plurality of specific polymerizable compounds in combination and a liquid crystal display element using the liquid crystal composition.

Description

Liquid crystal composition and liquid crystal display element

Technical Field

The present invention relates to a liquid crystal composition and a liquid crystal display element using the same.

Background

As liquid crystal display devices using liquid crystal compositions exhibiting negative dielectric anisotropy Δ ∈ liquid crystal TVs, liquid crystal displays, and the like of PSA and PSVA types have become widespread, and as liquid crystal compositions suitable for them, various polymerizable compounds and liquid crystal compositions containing them are disclosed in patent document 1, patent document 2, patent document 3, patent document 4, and patent document 5, and the like. Further, patent documents 6, 7, and 8 disclose a polymerizable compound having a biphenyl skeleton and a polymerizable compound having a terphenyl skeleton.

However, the characteristics of the liquid crystal compositions containing polymerizable compounds which have been conventionally used are insufficient for high-definition liquid crystal TVs such as 4K and 8K. In particular, the 4K and 8K liquid crystal display elements require high-definition pixels, and a considerable amount of UV light is filtered due to the increase of the wiring and the light shielding region. Therefore, in the UV irradiation step in the production of PSA-type and PSVA-type liquid crystal display devices, the polymerizable compound is not sufficiently polymerized, and a large amount of the polymerizable compound remains. As a result, the formation of the tilt angle became insufficient, and the following display defects were confirmed: the response speed IS deteriorated, the alignment property IS deteriorated, and the residual polymerizable compound IS slowly polymerized during driving to change the tilt angle, thereby burning the screen (IS). In addition, the presence of a substance whose tilt angle is easily changed and a substance whose tilt angle is not easily changed, which are characteristic of the polymerizable compound, was confirmed.

As described above, PSA or PSVA liquid crystal display elements such as high-definition 4K or 8K liquid crystal televisions and liquid crystal displays require extremely high characteristics that are clearly different from conventional techniques, and a liquid crystal composition that can be stably produced using UV light weaker or less than conventional ones is required.

Documents of the prior art

Patent document

Patent document 1: japanese patent laid-open publication No. 2016 and No. 216747

Patent document 2: japanese patent laid-open publication No. 2017-14486

Patent document 3: japanese patent No. 6008065

Patent document 4: japanese patent No. 6233550

Patent document 5: japanese patent No. 6087815

Patent document 6: chinese patent application publication No. 104342167 specification

Patent document 7: chinese patent application publication No. 104342170 specification

Patent document 8: international publication No. 2018/123417

Disclosure of Invention

Problems to be solved by the invention

The present invention addresses the problem of providing a polymerizable compound-containing liquid crystal composition that can achieve a high polymerization rate, a large tilt angle formation, a high tilt angle stability, and a high Voltage Holding Ratio (VHR) at the same time, and a PSA-type or PSVA-type liquid crystal display element that uses the composition and in which IS sufficiently suppressed or does not occur.

Means for solving the problems

As a result of intensive studies, the present inventors have found that the above problems can be solved by a liquid crystal composition containing 2 or more polymerizable compounds having a specific chemical structure, and have completed the present invention.

That is, an object of the present invention is to provide a liquid crystal composition containing a polymerizable compound represented by the general formula (RM-13) as a first component and a polymerizable compound represented by the general formula (RM-22) or (RM-23) as a second component.

[ solution 1]

(in the formula, P³And P⁴Each independently represents a polymerizable group represented by the formula (PG-1) to (PG-5), S³And S⁴Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂May be substituted by-O-, -OCO-or-COO-, Y¹To Y¹²Each independently represents an alkoxy group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, or a hydrogen atom, and at least one represents an alkoxy group having 1 to 5 carbon atoms or a fluoroalkoxy group having 1 to 5 carbon atoms. )

[ solution 2]

(wherein the hydrogen atoms in the methyl, ethyl, n-propyl and isopropyl groups bonded to the vinyl group may be substituted by 1Or 2 or more fluorine atoms, in which group-CH₂-may be substituted by oxygen atoms. )

[ solution 3]

(in the formula, P⁵、P⁶、P⁷And P⁸Each independently represents a polymerizable group represented by the formula (PG-1) to (PG-5), S⁵、S⁶、S⁷And S⁸Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂May be substituted by-O-, -OCO-or-COO-, A¹To A⁸Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, B¹To B¹²Each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom. )

[ solution 4]

(wherein hydrogen atoms in the methyl group, ethyl group, n-propyl group and isopropyl group bonded to the vinyl group may be substituted with 1 or 2 or more fluorine atoms, -CH in the group₂-may be substituted by oxygen atoms. )

Further, another object of the present invention is to provide a liquid crystal display element using the liquid crystal composition.

ADVANTAGEOUS EFFECTS OF INVENTION

The liquid crystal composition of the present invention can simultaneously realize a high polymerization rate, a large tilt angle formation, a high tilt angle stability, and a high VHR, and can provide a high-definition PSA-type or PSVA-type liquid crystal display element such as 4K or 8K, in which IS IS sufficiently suppressed or does not occur.

Detailed Description

The liquid crystal composition of the present invention contains a polymerizable compound represented by the general formula (RM-13) as a first component and contains a polymerizable compound represented by the general formula (RM-22) or the general formula (RM-23) as a second component.

[ solution 5]

[ solution 6]

In the formula (RM-13), P³And P⁴Each independently represents a polymerizable group represented by the formula (PG-1) to (PG-5).

[ solution 7]

(wherein hydrogen atoms in the methyl, ethyl, n-propyl and isopropyl groups bonded to the vinyl group may be substituted by 1 or 2 or more fluorine atoms, 1-CH in the group₂-or non-adjacent 2 or more-CH₂-may be substituted by oxygen atoms. ) Wherein, P³And P⁴The polymerizable group(s) of (b) is (are) preferably represented by the formula (PG-1) or (PG-2), and particularly preferably represented by the formula (PG-1).

S³And S⁴Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-, -OCO-or-COO-. Wherein S is³And S⁴Each independently is preferably a single bond or an unsubstituted alkylene group having 1 to 5 carbon atoms, and particularly preferably a single bond.

Y¹～Y¹²Each independently represents an alkoxy group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, or a hydrogen atom, and at least one represents an alkoxy group having 1 to 5 carbon atoms or a fluoroalkoxy group having 1 to 5 carbon atoms. Among them, Y is preferred¹～Y¹²At least one of them is an alkoxy group having 1 to 5 carbon atoms, and Y is particularly preferred¹～Y¹²At least one of (A) is methoxyAnd (4) a base.

The number of C1-5 alkoxy groups or C1-5 fluoroalkoxy groups is not particularly limited, and Y is preferably¹～Y¹²1 or 2 of them are alkoxy groups or fluoroalkoxy groups, the remainder being hydrogen atoms.

Y¹～Y¹²When 2 or more of the above groups are C1-5 alkoxy groups or C1-5 fluoroalkoxy groups, the 2 or more groups may be the same or different from each other. Among them, Y is preferred¹～Y¹²All groups other than the hydrogen atoms are the same group, and Y is particularly preferred¹～Y¹²All groups other than the hydrogen atoms are methoxy groups. In addition, 2 or more alkoxy groups or fluoroalkoxy groups may be substituted for a hydrogen atom bonded to the same benzene ring in the terphenyl, or may be substituted for a hydrogen atom bonded to a different ring. Examples of the case where 2 or more hydrogen atoms bonded to different rings are substituted with alkoxy or fluoroalkoxy include ring groups at both ends of terphenyl (as an example, in Y)¹And Y⁶Position(s) alkoxy substituted compounds.

In the formula (RM-22), A¹～A⁸Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom. Among them, A is preferable¹～A⁸All being hydrogen atoms or A¹～A⁸1 or 2 of (A) is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a fluorine atom, more preferably A¹～A⁸1 or 2 of (A) is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a fluorine atom, and A is particularly preferred¹～A⁸Is a methyl group, a methoxy group or a fluorine atom. A. the¹～A⁸When a plurality of (a) are groups or atoms other than hydrogen atoms, they may be the same group or atom or may be different groups or atoms.

In the formula (RM-23), B¹～B¹²Each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom. Among them, B is preferable from the viewpoint of solubility¹～B¹²1 in (1)One or 2 of them is C1-3 alkyl or fluorine atom, especially preferably B¹～B¹²1 or 2 of (a) are methyl or fluorine atoms. B is¹～B¹²When a plurality of (a) are groups or atoms other than hydrogen atoms, they may be the same group or atom or may be different groups or atoms.

In the formulae (RM-22) and (RM-23), P⁵、P⁶、P⁷And P⁸Each independently is a polymerizable group, and the description of the polymerizable group and the description of P³And P⁴The same applies to the polymerizable group (2). Wherein, P⁵、P⁶、P⁷And P⁸The polymerizable group(s) of (b) is (are) preferably represented by the formula (PG-1) or (PG-2), and particularly preferably represented by the formula (PG-1).

S⁵、S⁶、S⁷And S⁸Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-, -OCO-or-COO-. Wherein S⁵～S⁸Each independently is preferably a single bond or an unsubstituted alkylene group having 1 to 5 carbon atoms, and more preferably a single bond.

The polymerizable compound represented by the general formula (RM-13) as the first component is preferably a polymerizable compound represented by the general formulae (RM-131) to (RM-156), and particularly preferably a polymerizable compound represented by the general formulae (RM-131) to (RM-143).

[ solution 8]

[ solution 9]

[ solution 10]

[ solution 11]

(in the formula, P³、P⁴、S³And S⁴The same as described above. )

The polymerizable compound represented by the general formula (RM-22) which is the second component is preferably a polymerizable compound represented by the general formulae (RM-221) to (RM-225), general formulae (RM-22M1) to (RM-22M9), and general formulae (RM-22O1) to (RM-22O6), and particularly preferably a polymerizable compound represented by the general formulae (RM-22O1) to (RM-22O 6).

[ solution 12]

[ solution 13]

[ solution 14]

(in the formula, P⁵、P⁶、S⁵And S⁶The same as described above. )

The polymerizable compound represented by the general formula (RM-23) as the second component is preferably a polymerizable compound represented by the general formula (RM-231) to (RM-255).

[ solution 15]

[ solution 16]

[ solution 17]

(in the formula, P⁷、P⁸、S⁷And S⁸The same as described above. )

The content of the first component in the liquid crystal composition of the present invention is preferably 0.001 mass%, preferably 0.005 mass%, preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.1 mass%, preferably 0.2 mass%, preferably 0.3 mass%, preferably 0.4 mass%, and is preferably 3 mass%, more preferably 2 mass%, more preferably 1 mass%, more preferably 0.5 mass%, more preferably 0.4 mass%, more preferably 0.3 mass%, more preferably 0.2 mass%, and still more preferably 0.1 mass% as the lower limit. Hereinafter, the mass% may be referred to as%.

The content of the second component in the liquid crystal composition of the present invention is preferably 0.001 mass%, preferably 0.005 mass%, preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.1 mass%, preferably 0.2 mass%, preferably 0.3 mass%, preferably 0.4 mass%, and is preferably 3 mass%, more preferably 2 mass%, more preferably 1 mass%, more preferably 0.5 mass%, more preferably 0.4 mass%, and still more preferably 0.3 mass% as the lower limit.

The total content of the first component and the second component in the liquid crystal composition of the present invention is preferably 0.002 mass%, preferably 0.005 mass%, preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.1 mass%, preferably 0.2 mass%, preferably 0.3 mass%, preferably 0.4 mass%, and is preferably 6 mass%, preferably 3 mass%, more preferably 2 mass%, more preferably 1 mass%, more preferably 0.5 mass%, more preferably 0.4 mass%, and still more preferably 0.3 mass% as the lower limit.

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-01), (N-02), (N-03), (N-04) and (N-05). These compounds belong to the class of compounds having negative dielectric anisotropy. "compound having negative dielectric anisotropy" means a compound in which Δ ∈ has a negative sign and the absolute value thereof shows a value greater than 2. Wherein Δ ∈ of the compound is a value extrapolated from a measured value of dielectric anisotropy of a composition obtained by adding the compound to a composition having a substantially neutral dielectric property at 25 ℃.

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-01), (N-02), (N-03) and (N-04).

[ solution 18]

In the formula, R²¹And R²²Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-, Z¹Each independently represents a single bond, -CH₂CH₂-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH ═ CH-, -CF ═ CF-or-C ≡ C-, and m each independently represents 1 or 2.

R²¹The alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably an alkyl group having 1 to 4 carbon atoms. Wherein Z is¹When it represents a non-single bond, R²¹Preferably an alkyl group having 1 to 3 carbon atoms.

R²²Preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and still more preferably an alkoxy group having 1 to 4 carbon atoms.

R²¹And R²²In the case of alkenyl, it is preferableSelected from the group represented by any one of the formulae (R1) to (R5),

[ solution 19]

(the black dot in each formula represents a carbon atom in the ring structure.) is more preferably formula (R1) or formula (R2). Wherein R is²¹And R²²The content of the compound which is an alkenyl group is preferably as small as possible, and preferably not contained.

Z¹Each independently represents a single bond, -CH₂CH₂-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-, -CF-or-C.ident.C, preferably a single bond, -CH ≡ C₂CH₂-、-OCH₂-、-CH₂O-, more preferably a single bond or-CH₂O-。

When m is 1, Z¹Preferably a single bond.

When m is 2, Z¹Is preferably-CH₂CH₂-or-CH₂O-。

The fluorine atom of the compounds represented by the general formulae (N-01), (N-02), (N-03), (N-04) and (N-05) may be substituted with a chlorine atom which is also a halogen. Among them, the content of the compound substituted with a chlorine atom is preferably as small as possible, and preferably not contained.

The hydrogen atom present on the ring of the compounds represented by the general formulae (N-01), (N-02), (N-03), (N-04) and (N-05) may be substituted with a fluorine atom or a chlorine atom, but a chlorine atom is not preferred.

The compounds represented by the general formulae (N-01), (N-02), (N-03), (N-04) and (N-05) are preferably compounds having negative Δ ε and an absolute value of greater than 3. Specifically, R is preferred²²Represents an alkoxy group having 1 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms is particularly preferable.

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formula (N-01-1), the general formula (N-01-2), the general formula (N-01-3) and the general formula (N-01-4) as the compound represented by the general formula (N-01).

[ solution 20]

(in the formula, R²¹Represents the same meaning as described above, R²³Each independently represents an alkoxy group having 1 to 4 carbon atoms. )

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, and one or more compounds selected from the group of compounds represented by general formulae (N-01-1) to (N-01-4).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-01-1), and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-01-3), and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group consisting of compounds represented by the general formula (N-02-1), the general formula (N-02-2) and the general formula (N-02-3) as the compound represented by the general formula (N-02).

[ solution 21]

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, and a compound represented by the general formula (N-02-1).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-02-3).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (N-03-1) as the compound represented by the general formula (N-03).

[ solution 22]

(in the formula, R²¹Represents the same meaning as described above, R²³Represents an alkoxy group having 1 to 4 carbon atoms. )

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, and a compound represented by the general formula (N-03-1).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-03-1), and a compound represented by the general formula (N-01-4).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-03-1), and a compound represented by the general formula (N-02-1).

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-03-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-02-1).

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (N-04-1) as the compound represented by the general formula (N-04).

[ solution 23]

The liquid crystal composition of the present invention preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, and a compound represented by the general formula (N-04-1) at the same time.

The liquid crystal composition of the present invention particularly preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-04-1), and a compound represented by the general formula (N-01-4) at the same time.

The liquid crystal composition of the present invention particularly preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-02-1) at the same time.

The liquid crystal composition of the present invention particularly preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-03-1) at the same time.

The liquid crystal composition of the present invention particularly preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-03-1) at the same time.

The liquid crystal composition of the present invention particularly preferably contains a polymerizable compound as a first component, a polymerizable compound as a second component, a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-03-1) at the same time.

The liquid crystal composition of the present invention may contain a compound selected from the group of compounds represented by the formulae (N-05-1) to (N-05-3) as the compound represented by the general formula (N-05).

[ solution 24]

The lower limit of the preferable content of the compound represented by the general formula (N-01) is 0%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%, 15%, 10%.

The lower limit of the preferable content of the compound represented by the general formula (N-02) is 0%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%, 15%, 10%.

The lower limit of the preferable content of the compound represented by the general formula (N-03) is 0%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%, 15%, 10%.

The lower limit of the preferable content of the compound represented by the general formula (N-04) is 0%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%, 15%, 10%.

The lower limit of the preferable content of the compound represented by the formula (N-05) is 0%, 2%, 5%, 8%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%.

The liquid crystal composition of the present invention may further contain 1 or 2 or more compounds represented by the general formula (N-06).

[ solution 25]

(in the formula, R²¹And R²²The same meanings as described above are shown. )

The compound represented by the general formula (N-06) is effective for adjusting various physical properties, and can be used for obtaining a large refractive index anisotropy (. DELTA.n) and a high T_NILarge Δ ε.

The lower limit of the preferable content of the compound represented by the formula (N-06) is 0%, 2%, 5%, 8%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 5%.

The liquid crystal composition of the present invention contains 1 or 2 or more compounds selected from the group of compounds represented by general formulae (NU-01) to (NU-08).

[ solution 26]

(in the formula, R^NU11、R^NU12、R^NU21、R^NU22、R^NU31、R^NU32、R^NU41、R^NU42、R^NU51、R^NU52、R^NU61、R^NU62、R^NU71、R^NU72、R^NU81And R^NU82Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-. )

More specifically, R^NU11、R^NU12、R^NU21、R^NU22、R^NU31、R^NU32、R^NU41、R^NU42、R^NU51、R^NU52、R^NU61、R^NU62、R^NU71、R^NU72、R^NU81And R^NU82An alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms is more preferable. In the case where importance is attached to the response speed, at least 1R is preferable^NU11、R^NU21、R^NU41And R^NU51The alkenyl group having 2 to 3 carbon atoms is preferably an alkenyl group represented by the formula (R2).

The amount of the compound having an alkenyl group is preferably 30% or less, preferably 25% or less, preferably 20% or less, preferably 15% or less, preferably 10% or less, preferably 5% or less, based on the total amount of the liquid crystal composition of the present invention. When high VHR is regarded as important, the compound having an alkenyl group is preferably 10% or less, preferably 5% or less, preferably 1% or less, and is preferably not contained.

More specifically, R^NU11、R^NU21、R^NU31、R^NU41、R^NU51、R^NU61、R^NU71、R^NU81Particularly preferably an alkyl group of 1 to 5 carbon atoms, R^NU12、R^NU22、R^NU32、R^NU42、R^NU52、R^NU62、R^NU72And R^NU82Particularly preferred is an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-02).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-03).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-04).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-05).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-06).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-07).

The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-08).

The liquid crystal composition of the present invention preferably further contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), and a compound represented by the general formula (NU-04).

The liquid crystal composition of the present invention preferably further contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-03), and a compound represented by the general formula (NU-05).

The liquid crystal composition of the present invention preferably further contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), a compound represented by the general formula (NU-03), and a compound represented by the general formula (NU-05).

The content of the compound represented by the general formula (NU-01) is preferably 1 to 60% by mass, more preferably 10 to 50% by mass, and still more preferably 20 to 40% by mass.

The content of the compound represented by the general formula (NU-02) is preferably 1 to 40% by mass, more preferably 5 to 25% by mass, and still more preferably 5 to 20% by mass.

The content of the compound represented by the general formula (NU-03) is preferably 1 to 20% by mass, more preferably 0 to 15% by mass, and still more preferably 0 to 10% by mass.

The content of the compound represented by the general formula (NU-04) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and still more preferably 3 to 10% by mass.

The content of the compound represented by the general formula (NU-05) is preferably 1 to 30% by mass, more preferably 1 to 20% by mass, and still more preferably 3 to 20% by mass.

The content of the compound represented by the general formula (NU-06) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and still more preferably 3 to 10% by mass.

The content of the compound represented by the general formula (NU-07) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and still more preferably 3 to 10% by mass.

The content of the compound represented by the general formula (NU-08) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and still more preferably 3 to 10% by mass.

The liquid crystal composition of the present invention may contain 1 or 2 or more compounds having positive dielectric anisotropy described in paragraphs 0236 to 0509 of patent document 4 (Japanese patent No. 6233550).

The composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are bonded 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 composition, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially none, based on the total mass of the composition.

When importance is attached to the stability against UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% or less, preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.

The content of the compound having all the ring structures in the molecule as six-membered rings is preferably increased, and the content of the compound having all the ring structures in the molecule as six-membered rings is preferably 80% or more, more preferably 90% or more, further preferably 95% or more, and most preferably the composition is composed substantially of only the compound having all the ring structures in the molecule as six-membered rings, based on the total mass of the composition.

In order to suppress deterioration due to oxidation of the 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 is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.

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

In the present application, the term "substantially free" means that the composition does not contain any substance other than substances that are not intentionally contained.

The liquid crystal composition of the present invention may contain, in addition to the above-mentioned compounds, a conventional nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, an antioxidant, an ultraviolet absorber, a light stabilizer, an infrared absorber, or the like.

The liquid crystal composition of the present invention preferably contains an antioxidant so as not to be polymerized in a heat treatment which is one of the steps of manufacturing a liquid crystal display element. When the antioxidant is not contained, polymerization proceeds during the heat treatment before the UV irradiation step, and the desired orientation cannot be obtained.

As the antioxidant, hindered phenols represented by general formulae (H-1) to (H-4) can be mentioned.

[ solution 27]

In the general formulae (H-1) to (H-3), R^H1Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 2 to 10 carbon atoms. Further specifically, R^H1More preferably an alkyl group having 3 carbon atoms.

In the general formula (H-4), M^H1Represents an alkylene group having 4 to 10 carbon atoms (1 or 2 or more-CH in the alkylene group)₂-may be substituted by-O-, -CO-, -COO-, -OCO-in such a way that the oxygen atoms are not directly adjacent. ) -OCH₂-、-CH₂O-、-COO-、-OCO-、-CF₂O-、-OCF₂-、-CF₂CF₂-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -C ≡ C-, single bond, 1, 4-phenylene (any hydrogen atom in 1, 4-phenylene may be substituted with a fluorine atom), or trans-1, 4-cyclohexylene.

When the liquid crystal composition of the present invention contains an antioxidant, the lower limit thereof is preferably 10 mass ppm, preferably 20 mass ppm, preferably 50 mass ppm, and the upper limit thereof is 10000 mass ppm, preferably 1000 mass ppm, preferably 500 mass ppm, preferably 100 mass ppm.

Nematic phase-isotropic liquid phase transition temperature (T) of liquid crystal composition of the present invention_NI) From 60 ℃ to 120 ℃, more preferably from 70 ℃ to 100 ℃, and particularly preferably from 70 ℃ to 85 ℃. Wherein, in the present invention, T represents 60 ℃ or higher_NIHigh.

In the case of liquid crystal television applications, T_NIPreferably 70 to 80 ℃ in the case of mobile use, T_NIPreferably 80 to 90 ℃ and T is used for outdoor Display such as PID (Public Information Display)_NIPreferably from 90 to 110 ℃.

The liquid crystal composition of the present invention has a refractive index anisotropy (. DELTA.n) at 20 ℃ of 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. More specifically, the thickness is preferably 0.10 to 0.13 in the case of a thin cell gap, and is preferably 0.08 to 0.10 in the case of a thick cell gap. Among them, the refractive index anisotropy (. DELTA.n) of the liquid crystal composition of the present invention at 20 ℃ is particularly preferably 0.098 to 0.118.

The liquid crystal composition of the present invention has a rotational viscosity (. gamma.) at 20 ℃₁) Is from 50 to 160 mPas, preferably from 55 to 160 mPas, preferably from 60 to 160 mPas, preferably from 80 to 150 mPas, preferably from 90 to 140 mPas, preferably from 90 to 130 mPas, preferably from 90 to 115 mPas.

The liquid crystal composition of the present invention has a dielectric anisotropy (. DELTA.. di-elect cons.) at 20 ℃ of-1.7 to-4.0, preferably-1.7 to-3.5, more preferably-1.8 to-3.5, more preferably-1.9 to-3.3.

The liquid crystal composition of the present invention preferably contains the polymerizable compound of the first component and the polymerizable compound of the second component, further contains 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formula (N-01), the general formula (N-02), the general formula (N-03), the general formula (N-04), the general formula (N-05) and the general formula (N-06), and further contains 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formulae (NU-01) to (NU-08), and the upper limit of the total content thereof is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%, the total of these contents preferably has a lower limit of 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%, 100 mass%.

Particularly preferably, the liquid crystal composition of the present invention contains a first component polymerizable compound and a second component polymerizable compound, further contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-01), (N-02), (N-03) and (N-04), and further contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (NU-01) to (NU-08), and the upper limit of the total content thereof is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass% and 84 mass%, and the lower limit thereof is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%, 100 mass%.

The liquid crystal composition of the present invention can impart a sufficiently fast polymerization speed and a sufficiently large pretilt angle. In addition, the liquid crystal display element using the liquid crystal composition of the present invention has a small residual amount of polymerizable compound in the liquid crystal display element after polymerization, and display defects such as IS in high-definition PSA-type or PSVA-type liquid crystal display elements such as 4K and 8K do not occur or can be significantly suppressed. As described above, the production efficiency of high-definition PSA-type or PSVA-type liquid crystal display elements such as 4K and 8K can be significantly improved, and the industrial utility value is very high.

The liquid crystal composition of the present invention is suitable for the production of PSA-type or PSVA-type liquid crystal display devices, and also suitable for the production of NPS-type liquid crystal display devices. Further, it is also suitable for the case of producing a PI-less type liquid crystal display element characterized by having no alignment film.

The liquid crystal composition of the present invention is also suitable for a liquid crystal display element having no alignment film, i.e., a mode generally referred to as PI-less. For example, it is preferable to use a compound having a spontaneous alignment property described in Japanese patent application No. 2013-552125, Japanese application No. 2014-517515, Japanese patent No. 06081361, Japanese application No. 2015-546888, Japanese application No. 2017-12710, WO2017041893A, Japanese patent No. 06070973, WO17/047177, etc. in combination with the liquid crystal composition of the present invention.

The liquid crystal composition of the present invention is useful for liquid crystal display elements for active matrix driving, and can be used for liquid crystal display elements such as PSA, PSVA, PS-IPS, PS-FFS, and NPS.

The liquid crystal display device of the present invention preferably includes a 1 st substrate and a 2 nd substrate which are arranged to face each other, a common electrode provided on the 1 st substrate or the 2 nd substrate, a pixel electrode provided on the 1 st substrate or the 2 nd substrate and having a thin film transistor, and a liquid crystal layer containing a liquid crystal composition provided between the 1 st substrate and the 2 nd substrate. If necessary, an alignment film for controlling the alignment direction of liquid crystal molecules may be provided on the opposite side of at least one of the 1 st substrate and/or the 2 nd substrate so as to be in contact with the liquid crystal layer. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a known alignment film such as a rubbing alignment film (for example, polyimide), a photo alignment film (for example, decomposed polyimide), or the like can be used. Further, a color filter may be provided on the 1 st substrate or the 2 nd substrate as appropriate, or a color filter may be provided on the pixel electrode or the common electrode.

The 2 substrates of the liquid crystal cell used in the liquid crystal display element of the present invention may be made of a transparent material having flexibility such as glass or plastic, or may be made of an opaque material such as silicon. The transparent substrate having a transparent electrode layer can be obtained by, for example, sputtering Indium Tin Oxide (ITO) on a transparent substrate such as a glass plate.

The color filter can be produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. A method of producing a color filter by a pigment dispersion method will be described as an example, in which a curable color composition for a color filter is applied to the transparent substrate, subjected to patterning treatment, and then cured by heating or light irradiation. This process is performed for 3 colors of red, green, and blue, respectively, whereby a pixel portion for a color filter can be manufactured. Further, a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal resistivity element may be provided on the substrate.

Preferably, the 1 st substrate and the 2 nd substrate are opposed to each other with the common electrode and the pixel electrode layer inside.

The interval between the 1 st substrate and the 2 nd substrate may be adjusted by the spacer. In this case, the thickness of the light control layer is preferably adjusted to 1 to 100 μm. More preferably 1.5 to 10 μm, and when a polarizing plate is used, the product of the refractive index anisotropy Δ n of the liquid crystal and the cell thickness d is preferably adjusted so that the contrast becomes maximum. In addition, in the case where there are two polarizing plates, the adjustment can be performed in the following manner: the polarizing axes of the polarizing plates are adjusted to obtain good viewing angle and contrast. Further, a retardation film for enlarging a viewing angle may also be used. Examples of the spacer include glass particles, plastic particles, alumina particles, and photoresist. Then, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates so as to be provided with a liquid crystal injection port as necessary, the substrates are bonded to each other, and the sealant is thermally cured by heating.

The method of holding the liquid crystal composition between 2 substrates may be a common vacuum injection method, an ODF method, or the like.

As a method of polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention, it is preferable to carry out polymerization at an appropriate polymerization rate in order to obtain good alignment properties of the liquid crystal, and therefore, a method of polymerizing by irradiating active energy rays such as ultraviolet rays or electron rays alone or in combination or alternately is preferable. When ultraviolet light is used, either a polarized light source or an unpolarized light source may be used. In addition, when the polymerization is carried out in a state where the liquid crystal composition is held between 2 substrates, it is necessary that at least the substrate on the irradiation surface side has appropriate transparency to the active energy ray. Further, the following method may also be used: only a specific portion is polymerized by using a mask at the time of light irradiation, and then the orientation state of an unpolymerized portion is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further, active energy rays are irradiated for polymerization. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying a direct current electric field or an alternating current electric field to the liquid crystal composition. Among them, the applied alternating electric field is preferably alternating current having a frequency of 1Hz to 10kHz, more preferably 60Hz to 10kHz, and the voltage is selected according to the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled with the applied voltage. From the viewpoint of alignment stability and contrast, in the PSA type or PSVA type liquid crystal display element, the pretilt angle is preferably controlled to 80 degrees to 89.9 degrees.

In a PSA-type or PSVA-type liquid crystal display device, if a polymerizable compound IS not polymerized but remains as it IS after the device IS manufactured, IS occurs. The amount of the residual polymerizable compound is preferably 20ppm or less, more preferably 15ppm or less, particularly preferably 10ppm or less, and particularly preferably 0 or less as the lower limit of detection.

The temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron rays used for polymerization of the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited. For example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate with an alignment film, the liquid crystal composition is preferably kept in a liquid crystal state within a temperature range. Namely, the polymerization is preferably carried out at 15 to 50 ℃.

As the lamp for generating ultraviolet rays, a metal halide lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, or the like can be used, and an ultrahigh-pressure UV lamp by usio corporation and a fluorescent ultraviolet lamp by TOSHIBA corporation are preferable. The wavelength of the ultraviolet light to be irradiated is preferably ultraviolet light whose irradiation wavelength region is not in the absorption wavelength region of the liquid crystal composition, and the ultraviolet light is preferably filtered and used as necessary. The intensity of the ultraviolet ray to be irradiated is preferably 0.1mW/cm²～100W/cm²More preferably 2mW/cm²～50W/cm². The energy of the ultraviolet rays to be irradiated may be appropriately adjusted, and is preferably 10mJ/cm²To 500J/cm²More preferably 100mJ/cm²To 200J/cm²。

Examples

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the compositions of examples and comparative examples below, "%" means "% by mass". The compounds described in the examples are as follows.

Unless otherwise specified, the respective physical property values were measured by the methods described in standards JEITAED-2521B, modified in 2009 at 3 months, issued by the society of electronic information technology industries (the electronic situation technology would make JEITA ED-2521B, modified in 2009 at 3 months, the company legal industry technology ).

(side chain)

(linker)

(Ring structure)

[ solution 28]

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

Δ ε: anisotropy of dielectric constant at 20 DEG C

γ₁: rotational viscosity (mPa. multidot.s) at 20 DEG C

RM: illumination intensity of 313nm for 20 minutes of 3mW/cm²Residual monomer amount (ppm) in the liquid crystal display element after UV light of (1)

Tilt: illumination intensity of 313nm for 2 minutes of irradiation of 3mW/cm²Shows a change amount from 90 ° after UV light of (a) to (b).

IS: illumination intensity of 313nm for 60 minutes of preparation for 3mW/cm²The liquid crystal display element after UV light of (1) maintains the driving state for a certain time, and then the variation of the pretilt angle is changed to a value of 100 times

VHR: illumination intensity of 313nm for 60 minutes of preparation for 3mW/cm²The voltage holding ratio (%), measured under the conditions of 1V, 60Hz, and 60 ℃ of the UV-irradiated liquid crystal display device of (1)

(preparation of liquid Crystal composition and evaluation results)

Liquid crystal compositions (LC-1) to (LC-4) were prepared, and their physical property values were measured. The component ratios of these liquid crystal compositions and their physical property values are shown in table 1.

[ Table 1]

Examples 1(E-01) to 4(E-04) and comparative examples 1(C-01) to 2(C-02) were prepared by mixing these liquid crystal compositions with polymerizable compounds represented by the formulae (RM-131-MM) and/or (RM-22O2-MM), and RM, Tilt, IS and VHR were evaluated, and the results are shown in Table 2.

[ solution 29]

[ Table 2]

The RMs in examples 1(E-01) to 4(E-04) were 0 or less, which is a sufficiently small value, at the lower detection limit. Further, it was confirmed that Tilt, IS and VHR were sufficiently large, respectively. From the above, it was confirmed that the embodiments solve the problems of the present invention. On the other hand, it was confirmed that IS in comparative example 1(C-01) was 120, which IS very large, RM in comparative example 2(C-02) was as large as 21, and Tilt was small. As described above, it was confirmed that these comparative examples could not solve the problems of the present invention.

[ solution 30]

The problem of the present invention was solved by preparing a composition in which the polymerizable compound represented by the formula (RM-22O2-MM) contained in examples 1(E-01) to 4(E-04) was replaced with the polymerizable compound represented by the formula (RM-22O 1-MM).

When the polymerizable compound represented by the formula (RM-22O2-MM) contained in example 4(E-04) was replaced with the polymerizable compound represented by the formula (RM-224-MM), good results were obtained although slightly inferior to example (E-04).

When the polymerizable compound represented by the formula (RM-22O2-MM) contained in example 4(E-04) was replaced with the polymerizable compound represented by the formula (RM-22M5-MM), good results were obtained although slightly inferior to those in example (E-04).

[ solution 31]

Further, a composition prepared by adding 50ppm of an antioxidant represented by the formula (H-2-R3) to example 1(E-01) was prepared, and it was confirmed that the object of the present invention was achieved. Furthermore, a composition prepared by adding 50ppm of an antioxidant represented by the formula (H-3-R3) to example 1(E-01) was prepared, and it was confirmed that the problem of the present invention was solved. A composition prepared by adding 50ppm of an antioxidant represented by the formula (H-4-M8) to example 1(E-01) was prepared, and it was confirmed that the problem of the present invention was solved.

A composition prepared by adding 20ppm of an antioxidant represented by the formula (H-2-R3) to example 4(E-04) was prepared, and it was confirmed that the problem of the present invention was solved. Furthermore, a composition prepared by adding 20ppm of an antioxidant represented by the formula (H-3-R3) to example 4(E-04) was prepared, and it was confirmed that the problem of the present invention was solved. A composition prepared by adding 10ppm of an antioxidant represented by the formula (H-4-M8) to example 4(E-04) was prepared, and it was confirmed that the problem of the present invention was solved.

Examples 5(E-05) to 10(E-10) were prepared by mixing the liquid crystal composition with a polymerizable compound represented by the formula (RM-131-MM), the formula (RM-137-MM), the formula (RM-22O1-MM) and/or the formula (RM-22O2-MM), and RM, Tilt, IS and VHR were evaluated, and the results are shown in Table 3.

[ Table 3]

The RMs of examples 5(E-05) to 10(E-10) were 0 below the lower limit of detection, and were sufficiently small values. Further, it was confirmed that Tilt IS a sufficiently large value, IS IS a sufficiently small value, and VHR IS a sufficiently high value. From the above, it was confirmed that the embodiments solve the problems of the present invention.

Claims

1. A liquid crystal composition containing a polymerizable compound represented by the general formula (RM-13) as a first component and a polymerizable compound represented by the general formula (RM-22) or the general formula (RM-23) as a second component,

[ solution 1]

In the formula, P³And P⁴Each independently represents a polymerizable group represented by the formula (PG-1) to (PG-5), S³And S⁴Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂May be substituted by-O-, -OCO-or-COO-, Y¹To Y¹²Each independently represents an alkoxy group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms or a hydrogen atom, at least one represents an alkoxy group having 1 to 5 carbon atoms or a fluoroalkoxy group having 1 to 5 carbon atoms,

[ solution 2]

Wherein hydrogen atoms in the methyl, ethyl, n-propyl and isopropyl groups bonded to the vinyl group may be substituted by 1 or 2 or more fluorine atoms in which-CH₂-can be substituted by an oxygen atom,

[ solution 3]

In the formula, P⁵、P⁶、P⁷And P⁸Each independently represents a polymerizable group represented by the formula (PG-1) to (PG-5), S⁵、S⁶、S⁷And S⁸Each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, 1-CH in the alkylene group₂-or non-adjacent 2 or more-CH₂May be substituted by-O-, -OCO-or-COO-, A¹To A⁸Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, B¹To B¹²Each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,

[ solution 4]

Wherein hydrogen atoms in the methyl, ethyl, n-propyl and isopropyl groups bonded to the vinyl group may be substituted by 1 or 2 or more fluorine atoms in which-CH₂-may be substituted by oxygen atoms.

2. The liquid crystal composition according to claim 1, further comprising 1 or 2 or more compounds selected from the group consisting of compounds represented by the general formula (N-01), the general formula (N-02), the general formula (N-03), the general formula (N-04), and the general formula (N-05),

[ solution 5]

In the formula, R²¹And R²²Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other₂Each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -, -CCOO-or-OCO-substituted, Z¹Each independently represents a single bond, -CH₂CH₂-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH ═ CH-, -CF ═ CF-or-C ≡ C-, and m each independently represents 1 or 2.

3. The liquid crystal composition according to claim 1 or 2, further comprising 1 or 2 or more compounds selected from the group of compounds represented by general formulae (NU-01) to (NU-08),

[ solution 6]

In the formula, R^NU11、R^NU12、R^NU21、R^NU22、R^NU31、R^NU32、R^NU41、R^NU42、R^NU51、R^NU52、R^NU61、R^NU62、R^NU71、R^NU72、R^NU81And R^NU82Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-.

4. The liquid crystal composition according to any one of claims 1 to 3, which contains a polymerizable compound represented by general formulae (RM-131) to (RM-143) as a first component and a polymerizable compound represented by general formulae (RM-22O1) to (RM-22O6) as a second component,

[ solution 7]

[ solution 8]

In the formula, P³、P⁴、S³、S⁴Respectively, as in the above-described case,

[ solution 9]

In the formula, P⁵、P⁶、S⁵、S⁶The same applies to each of the above.

5. The liquid crystal composition according to any one of claims 1 to 4, further comprising an antioxidant represented by the formula (H-2-R3), the formula (H-3-R3) or the formula (H-4-M8),

[ solution 10]

6. The liquid crystal composition according to any one of claims 1 to 5, wherein the total content of the first component, the second component, the compound selected from the group consisting of the compounds represented by the general formulae (N-01) to (N-04), and the compound selected from the group consisting of the compounds represented by the general formulae (NU-01) to (NU-08) is 80 to 100% by mass relative to the total amount of the composition.

7. The liquid crystal composition according to any one of claims 1 to 6, wherein the first component is contained in an amount of 0.01 to 0.10% by mass based on the total amount of the composition, and the second component is contained in an amount of 0.2 to 0.5% by mass based on the total amount of the composition.

8. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 7.

9. A liquid crystal display device for driving an active matrix, which comprises the liquid crystal composition according to any one of claims 1 to 7.

10. A PSA type or PSVA type liquid crystal display device using the liquid crystal composition according to any one of claims 1 to 7.

11. A liquid crystal display element having no alignment film, which uses the liquid crystal composition according to any one of claims 1 to 7.