WO2019124345A1 - 重合性液晶組成物及び液晶表示素子ならびに重合性化合物 - Google Patents

重合性液晶組成物及び液晶表示素子ならびに重合性化合物 Download PDF

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WO2019124345A1
WO2019124345A1 PCT/JP2018/046502 JP2018046502W WO2019124345A1 WO 2019124345 A1 WO2019124345 A1 WO 2019124345A1 JP 2018046502 W JP2018046502 W JP 2018046502W WO 2019124345 A1 WO2019124345 A1 WO 2019124345A1
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carbon atoms
general formula
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present
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French (fr)
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淳子 山本
雄一 井ノ上
純一 間宮
正臣 木村
林　正直
弘和 杉山
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Dic株式会社
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Priority to CN201880077813.7A priority Critical patent/CN111417700B/zh
Priority to JP2019561094A priority patent/JP6801796B2/ja
Priority to KR1020207016232A priority patent/KR20200100628A/ko
Publication of WO2019124345A1 publication Critical patent/WO2019124345A1/ja

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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a liquid crystal composition (polymerizable liquid crystal composition) containing a polymerizable compound, a liquid crystal display device using the same, and a polymerizable compound.
  • liquid crystal display devices such as liquid crystal panels and liquid crystal displays
  • the state of alignment of liquid crystal molecules is changed by an external stimulus such as an electric field, and the change in optical characteristics accompanying this is used for display.
  • a liquid crystal display element has a configuration in which liquid crystal molecules are filled in a gap between two transparent substrates, and liquid crystal molecules are arranged in a specific direction in advance on the surface of the substrate in contact with the liquid crystal molecules.
  • an alignment film is formed.
  • the alignment film is generally manufactured by rubbing a polyimide film, but when the alignment is given by rubbing, there is a problem that an alignment defect is generated due to a scratch or dust generated on the surface of the alignment film. Furthermore, the rubbing method has not been able to cope with the requirement that the liquid crystal display element takes a plurality of different alignment directions in the pixel.
  • liquid crystal display elements in which the initial alignment state (state in which a voltage is not applied) of liquid crystal molecules is perpendicular to the substrate (VA system) and some are horizontal.
  • VA system the initial alignment state
  • a voltage is usually applied between two substrates, and the liquid crystal composition having a negative dielectric anisotropy ( ⁇ ) is laid horizontally with respect to the substrate to change the optical characteristics and display. Is going.
  • the VA system has been put to practical use as a PSA (Polymer Sustained Alignment) liquid crystal display device using a cured product of a polymerizable compound in order to regulate the falling direction of the liquid crystal compound (Patent Document 1).
  • PSA type liquid crystal display device has a structure in which a polymer structure is formed in a cell in order to control the pretilt angle of liquid crystal molecules, and has an advantage that high-speed response and high contrast can be realized.
  • this PSA type liquid crystal display element In the production of this PSA type liquid crystal display element, a polymerizable compound-containing liquid crystal composition consisting of a polymerizable compound and a liquid crystal compound is injected between the substrates, and a voltage is applied to polymerize the polymerizable compound in the aligned liquid crystal molecules. This is done by fixing the orientation of the liquid crystal molecules. As a result, liquid crystal molecules aligned vertically to the substrate by the alignment film are inclined, and the alignment direction is restricted (pretilt angle is given). As causes of burn-in, which is a display defect of this PSA type liquid crystal display element, it is known that due to impurities and change in alignment of liquid crystal molecules (change in pretilt angle). Therefore, it is possible to provide the required initial pretilt angle, and it is important that the pretilt angle does not change with time.
  • Patent Document 2 As a method of aligning liquid crystal molecules perpendicularly to a substrate, a method using a compound having a self-orientation property without using an alignment film has been developed (Patent Document 2). In this method, it is necessary to develop a polymerizable liquid crystal compound which satisfies the requirement for the pretilt angle, as well as vertically aligning the liquid crystal compound together with the compound having the self alignment property.
  • a desired pretilt angle is given while satisfying the requirements such as high-speed response, low voltage drive, high contrast and long-term reliability which are conventionally required for liquid crystal display elements. It is an object of the present invention to provide a polymerizable liquid crystal composition in which a change in the pretilt angle does not occur or the change is suppressed, and to provide a liquid crystal display device and a polymerizable compound using the same.
  • the polymerizable liquid crystal composition according to the present invention is excellent in the compatibility between the liquid crystal compound and the polymerizable compound, the precipitation at a low temperature can be suppressed for a long period of time.
  • the liquid crystal display device using the polymerizable liquid crystal composition according to the present invention is excellent because the desired pretilt is imparted while satisfying the characteristics conventionally required for the liquid crystal display device and the pretilt angle does not change over a long period of time It has display characteristics.
  • FIG. 1 It is a photograph under the cross nicol of the cell which inject
  • FIG. 2 It is a photograph under cross nicol of the cell which inject
  • FIG. 1 It is a photograph under cross nicol of the cell which inject
  • the present invention relates to a polymerizable compound represented by the general formula (i)
  • a i2 represents the following group (a) and group (b) (A) cyclopentane-1,2,3-triyl, cyclopentane-1,3,4-triyl, cyclohexane-1,3,4-triyl or cyclohexane-1,3,5-triyl (which are present in this group
  • R i1 is a hydrogen atom (does not become a hydrogen atom when n i1 is 0 described later), an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, a nitro It represents a hydrogen atom in the alkyl group halogen, cyano group, a nitro group, and P i3 -Sp i3 - - group or P i3 -Sp i3 may be substituted with, existing in the alkyl group
  • One or more -CH 2- may be replaced by -O-, -COO- or -OCO- so that the oxygen atom is not directly linked, and one -CH 2 present in the alkyl group CH 2 -or 2 or more -CH 2 CH 2
  • Group (a), group (b) and group (c) are each independently an alkyl group having 1 to 12 carbon atoms, or 1 to 12 carbon atoms.
  • alkoxy group, a halogen, a cyano group, a nitro group, or P i3 -Sp i3 - (hydrogen atom in the alkyl group halogen, cyano group, a nitro group, and P i3 -Sp i3 - may be substituted with,
  • One or more -CH 2- present in the alkyl group may be replaced by -O-, -COO- or -OCO- so that the oxygen atom is not directly linked, and is present in the alkyl group to one -CH 2 CH 2 - or two or more -CH 2 CH 2 -.
  • R 21 , R 31 , R 41 , R 51 and R 61 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • W is a single bond, -O- or a methylene group
  • T is a single bond or -COO-
  • p, t and q are each independently 0, 1 or 2.
  • Sp i1, Sp i2 and Sp i3 are each independently a single bond or an alkylene group having 1 to 15 carbon atoms, one in the alkylene group or two or more -CH 2 - may have an oxygen atom so as not to directly adjacent, -O -, - OCO- or -COO- in may be substituted, one or more hydrogen atoms in the alkylene group, halogen, a cyano group, P i3 -Sp i3 - or an alkyl group having 1 to 12 carbon atoms (the alkyl group is
  • the present invention provides a polymerizable liquid crystal composition containing one or more components, a polymerizable liquid crystal composition further containing a spontaneous orientation compound in addition to the polymerizable compound, and a liquid crystal display device using the polymerizable liquid crystal composition.
  • the present invention also provides a polymerizable compound represented by the general formula (ii).
  • R i2 represents an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen, a nitro group (the hydrogen atom in the alkyl group is fluorine, It may be substituted by a cyano group or a nitro group, and one or more -CH 2- present in the alkyl group may be -O-, -COO- or -OCO- so that the oxygen atom is not directly linked.
  • a i2 is a group (a) and a group (b) below (A) cyclopentane-1,2,3-triyl, cyclopentane-1,3,4-triyl, cyclohexane-1,3,4-triyl or cyclohexane-1,3,5-triyl (which are present in this group).
  • Group (a), group (b) and group (c) are each independently an alkyl group having 1 to 12 carbon atoms, or 1 to 12 carbon atoms.
  • alkoxy group, a halogen, a cyano group, a nitro group, or P i3 -Sp i3 - (hydrogen atom in the alkyl group halogen, cyano group, a nitro group, and P i3 -Sp i3 - may be substituted with,
  • One or more -CH 2- present in the alkyl group may be replaced by -O-, -COO- or -OCO- so that the oxygen atom is not directly linked, and is present in the alkyl group to one -CH 2 CH 2 - or two or more -CH 2 CH 2 -.
  • R 21 , R 31 , R 41 , R 51 and R 61 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • W is a single bond, -O- or a methylene group
  • T is a single bond or -COO-
  • p, t and q are each independently 0, 1 or 2.
  • Sp i1, Sp i2 and Sp i3 are each independently a single bond or an alkylene group having 1 to 15 carbon atoms, one in the alkylene group or two or more -CH 2 - may have an oxygen atom so as not to directly adjacent, -O -, - OCO- or -COO- in may be substituted, one or more hydrogen atoms in the alkylene group, halogen, a cyano group, P i3 -Sp i3 - or an alkyl group having 1 to 12 carbon atoms (the alkyl group is
  • n i1 is 0, 1, 2 or 3, R i2 in the same molecule
  • a il , L il , P i3 , S i3 and R a may be identical to or different from each other.
  • the polymerizable compound represented by the general formula (ii) imparts excellent vertical alignment to liquid crystal molecules, and provides a liquid crystal composition excellent in compatibility.
  • liquid crystal molecules can be vertically aligned without the need for an alignment film.
  • the compound represented by general formula (i) can also be used independently, it can also be used combining two or more compounds. Although there is no restriction
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the general formula (i) to the total amount of the composition of the present invention is 0.01%, 0.04% and 0.07%. 0.1%, 0.13%, 0.16%, 0.2%, 0.23%, 0.26%, 0.3%, It is 0.33%, 0.36%, 0.40% and 0.45%.
  • the upper limit of the preferred content is 3%, 2.5%, 2%, 2%, 1%, 0.9%, 0.8%, 0.7% , 0.6% and 0.5%.
  • the above lower limit value is high and the upper limit value is high in order to improve the sticking property of the composition of the present invention and maintain the vertical orientation.
  • the vertical alignment property of the liquid crystal composition is set by setting the lower limit value of the content of the compound represented by general formula (i) high. Is preferable because it improves.
  • the upper limit value is too high, it is not preferable because problems such as unpolymerized polymerizable compounds remain after irradiation with ultraviolet light.
  • the above lower limit value is low and the upper limit value is low.
  • the polymerizable liquid crystal composition is dropped onto the substrate, in the case of improving the drop mark where display unevenness occurs at the dropped point, it is preferable to set the range of the content to the middle.
  • the polymerizable compound of the present invention is represented by the general formula (i).
  • a i2 examples include cyclohexane-1,3,4-triyl or cyclohexane-1,3,5-triyl, benzene-1,3,4-triyl, benzene-1, 3,5-triyl, naphthalene-2,5,6-triyl, naphthalene-2,6,7-triyl, naphthalene-2,5,7-triyl, naphthalene-1,4,5-triyl, phenanthrene-3, 6,9-triyl, phenanthrene-1,3,7-triyl, phenanthrene-3,5,9-triyl, phenanthrene-2,7,9-triyl, phenanthrene-4,5,9-triyl or phenanthrene-4, Preferred is 6,9-triyl, particularly preferably cyclohexane-1,3,5-triyl, benzene-1,3,5-triyl, na
  • these groups are alkyl groups having 1 to 12 carbon atoms, halogenated alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms (provided that one or more of them are present in the alkyl group).
  • -CH 2- may be replaced by -O-, -COO- or -OCO- so that the oxygen atom is not directly linked), a halogen, a cyano group, a nitro group, P i3 -S i3 -or R il - (A il -L il ) ni1 - may be substituted with.
  • R i1 is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group or a nitro group, provided that one or more members exist in the alkyl group.
  • -CH 2 - may be replaced by -O-, -COO- or -OCO-, fluorine so that the oxygen atom is not directly linked, and one -CH 2 CH present in the alkyl group.
  • P i1 , P i2 and P i3 each independently represent any of the formulas (R-I) to (R-IX), and in particular (R-I), (R-III), (R-) VIII) is preferred.
  • R 21 , R 31 , R 41 , R 51 and R 61 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • W is a single bond, -O- or a methylene group
  • T is a single bond or -COO-
  • p, t and q are each independently 0, 1 or 2.
  • Sp i1, Sp i2 and Sp i3 are each independently a single bond or an alkylene group having 1 to 15 carbon atoms, one in the alkylene group or two or more -CH 2 - may have an oxygen atom so as not to directly adjacent, -O -, - OCO- or -COO- in may be substituted, one or more hydrogen atoms in the alkylene group, halogen, a cyano group, P i3 -Sp i3 - or an alkyl group having 1 to 12 carbon atoms (the alkyl group is
  • n i1 represents 0, 1, 2 or 3, preferably 0, 1 or 2 and 1 or 2 is preferable.
  • R il in the same molecule A il, L il, P i3, if Sp i3 and R a are present in plural, plural R il, A il, L il , P i3, Sp i3 and Ra may be the same or different.
  • the compound represented by General Formula (i) is preferably a compound selected from the group of compounds represented by General Formulas (i-1) to (i-35).
  • composition of the present invention preferably contains one or more compounds selected from the compounds represented by the general formulas (N-1), (N-2) and (N-3). These compounds correspond to dielectrically negative compounds (the sign of ⁇ is negative and its absolute value is larger than 2).
  • R N11 , R N12 , R N21 , R N22 , R N31 and R N32 each independently have 1 to 8 carbon atoms Alkyl group, alkoxy group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms or alkenyloxy group having 2 to 8 carbon atoms is preferable, and alkyl group having 1 to 5 carbon atoms, the number of carbon atoms An alkoxy group of 1 to 5, an alkenyl group of 2 to 5 carbon atoms or an alkenyloxy group of 2 to 5 carbon atoms is preferable, and an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferable, and an alkenyl group having 3 carbon atoms (propen
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon Alkenyl group having 4 to 5 atoms is preferable
  • a linear alkyl group having 1 to 5 carbon atoms, a straight chain Preferred is an alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in the ring structure.)
  • a N 11 , A N 12 , A N 21 , A N 22 , A N 31 and A N 32 are each preferably aromatic when it is required to increase ⁇ n independently, and in order to improve the response speed, it is preferable to use fat Group is preferred, and trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 Be 2,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl Preferred, it is more preferable that represents the following structures,
  • it represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group.
  • Z N11, Z N12, Z N21 , Z N22, Z N31 and Z N32 -CH 2 each independently O -, - CF 2 O - , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents an, -CH 2 O -, - CH 2 CH 2 - or a single bond is more preferable, -CH 2 O-or a single bond is particularly preferred.
  • X N21 is preferably a fluorine atom.
  • T N31 is preferably an oxygen atom.
  • n N 11 + n N 12 , n N 21 + n N 22 and n N 31 + n N 32 are preferably 1 or 2, and combinations in which n N 11 is 1 and n N 12 is 0, n N 11 is 2 and n N 12 is 0, n A combination in which N 11 is 1 and n N 12 is 1, a combination in which n N 11 is 2 and n N 12 is 1, a combination in which n N 21 is 1 and n N 22 is 0, n N 21 is 2 and n N 22 is A combination of 0, a combination of n N31 of 1 and n N32 of 0, and a combination of n N31 of 2 and n N32 of 0 is preferred.
  • the lower limit of the preferable content of the compound represented by the formula (N-1) to the total amount of the composition of the present invention is 1%, 10%, 20%, and 30%. 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the lower limit of the preferable content of the compound represented by the formula (N-2) to the total amount of the composition of the present invention is 1%, 10%, 20%, 30% 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the lower limit of the preferable content of the compound represented by the formula (N-3) to the total amount of the composition of the present invention is 1%, 10%, 20%, and 30%. 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the above lower limit is low and the upper limit is low. Furthermore, when the composition of the present invention has a high T ni and a composition having good temperature stability is required, it is preferable that the above lower limit is low and the upper limit is low. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above lower limit value be high and the upper limit value be high.
  • Examples of the compound represented by General Formula (N-1) include compounds represented by the following General Formulas (N-1a) to (N-1g).
  • R N11 and R N12 are as defined R N11 and R N12 in the general formula (N-1), n Na11 represents 0 or 1, n NB11 is 1 or 2, n NC11 is N Nd11 represents 1 or 2; n Ne11 represents 1 or 2; n Nf12 represents 1 or 2; n Ng11 represents 1 or 2; A Ne11 represents trans-1, 4 And A Ng 11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, but at least one of represents a 1,4-cyclohexenylene group, Z NE11 at least one present in the represents a single bond or ethylene molecules represent ethylene, a NE11 a plurality present in the molecule, Z Ne 1, and / or A NG11 may or may not be the same.
  • the compound represented by General Formula (N-1) is a compound selected from the group of compounds represented by General Formulas (N-1-1) to
  • the compounds represented by General Formula (N-1-1) are the following compounds.
  • R N111 and R N112 each independently represent the same meaning as R N11 and R N12 in General Formula (N-1).
  • R N 111 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably a propyl group, a pentyl group or a vinyl group.
  • RN 112 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group or butoxy group.
  • the compounds represented by General Formula (N-1-1) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-1) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%.
  • the upper limit of the preferred content is 50%, 40%, 38%, 35%, 33%, 30%, or 50%, based on the total weight of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5% and 3%.
  • the compound represented by General Formula (N-1-1) is a compound selected from the group of compounds represented by Formula (N-1-1.1) to Formula (N-1-1.25) And the compounds represented by the formulas (N-1-1.1) to (N-1-1.4) are preferable, and the compounds represented by the formulas (N-1-1.1) and (N The compound represented by -1-1.3) is preferred.
  • the compounds represented by the formulas (N-1-1.1) to (N-1-1.25) can be used alone or in combination, but the compounds of the present invention
  • the lower limit of the preferable content of these compounds alone or in the total amount is 5%, 10%, 13%, 15%, 17%, 20%, 23% 25%, 27%, 30%, 33% and 35%.
  • the upper limit of the preferred content is 50%, 40%, 38%, 35%, 33%, 30%, or 50%, based on the total weight of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5% and 3%.
  • the compounds represented by formula (N-1-2) are the following compounds.
  • R N121 and R N122 each independently represent the same meaning as R N11 and R N12 in General Formula (N-1).
  • RN 121 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group or a pentyl group.
  • R N 122 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 a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group is preferable.
  • the compounds represented by General Formula (N-1-2) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-2) to the total amount of the composition of the present invention is 5%, 7%, 10%, 13% , 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37% 40% and 42%.
  • the upper limit of the preferred content is 50%, 48%, 45%, 43%, 40%, 38%, 35%, based on the total weight of the composition of the present invention. %, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 18%, 15%, 13%, 10%. %, 8%, 7%, 6%, 5%.
  • the compound represented by the general formula (N-1-2) is a compound selected from the group of compounds represented by the formula (N-1-2.1) to the formula (N-1-2.25) It is preferable that the formula (N-1-2.3) to the formula (N-1-2.7), the formula (N-1-2.10), the formula (N-1-2.11), the formula Preferred are the compounds represented by (N-1-2.13) and the formula (N-1-2.20), and in the case of emphasizing the improvement of .DELTA..epsilon.
  • the compounds represented by the formula (N-1-2.1) to the formula (N-1-2.25) may be used alone or in combination, but the composition of the present invention
  • the lower limit of the preferred content of these compounds alone or in the total amount of these is 5%, 10%, 13%, 15%, 17%, 20%, 23 %, 25%, 27%, 30%, 33%, 35%.
  • the upper limit of the preferred content is 50%, 40%, 38%, 35%, 33%, 30%, or 50%, based on the total weight of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5% and 3%.
  • the compounds represented by formula (N-1-3) are the following compounds.
  • R N 131 and R N 132 each independently represent the same meaning as R N 11 and R N 12 in General Formula (N-1).
  • R N 131 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N 132 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 3 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and 1-propenyl group, ethoxy group, propoxy group or butoxy group is preferable .
  • the compounds represented by General Formula (N-1-3) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-3) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3-21) And the compounds represented by formulas (N-3.1) to (N-1-3.7) and formula (N-1-3.21) are preferable.
  • -1-3.1), the formula (N-1-3.2), the formula (N-1-3.3), the formula (N-1-3.4) and the formula (N-1-3.6) The compounds represented by) are preferred.
  • the compounds represented by the formulas (N-1-3.1) to (N-1-3.4), the formulas (N-1-3.6) and the formulas (N-1 3.21) can be used alone. Although it is possible to use in combination or in combination, a combination of formula (N-1-3.1) and formula (N-1-3.2), a formula (N-1-3.3) Or a combination of two or three selected from formula (N-1-3.4) and formula (N-1-3.6).
  • the lower limit of the preferred content of these compounds alone or in the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20 %.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-4) are the following compounds.
  • R N141 and R N 142 independently represents the same meaning as R N 11 and R N 12 in General Formula (N-1).
  • R N141 and R N142 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 4-5 preferably a methyl group, a propyl group, an ethoxy Preferred is a group or butoxy group.
  • the compounds represented by General Formula (N-1-4) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-4) to the total amount of the composition of the present invention is 3%, 5%, 7%, 10% 13%, 15%, 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15%, 13%, 11%, 10%, 8%.
  • the compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formula (N-1 -4.1) to the formula (N-1 -4.24) And the compounds represented by formulas (N-1-4.1) to (N-1 -4.4) are preferable, and the compounds represented by formulas (N-1-4.1) and (N Preferred are the compounds represented by -1-4.2) and the formula (N-1-4.4).
  • the compounds represented by formulas (N-1-4.1) to (N-1-4.24) can be used alone or in combination, but the compounds of the present invention
  • the lower limit of the preferred content of these compounds alone or in the total amount is 3%, 5%, 7%, 10%, 13%, 15%, 17% And 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15%, 13%, 11%, 10%, 8%.
  • the compounds represented by General Formula (N-1-5) are the following compounds.
  • R N 151 and R N 152 each independently represent the same meaning as R N 11 and R N 12 in General Formula (N-1).
  • Each of R N151 and R N152 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, preferably an ethyl group, a propyl group or a butyl group Is preferred.
  • the compounds represented by General Formula (N-1-5) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-5) to the total amount of the composition of the present invention is 5%, 8%, 10%, 13% 15%, 17% and 20%.
  • the upper limit value of the preferred content is 35%, 33%, 30%, 28%, 25%, 23%, or 35%, based on the total weight of the composition of the present invention. %, 18%, 15% and 13%.
  • the compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formula (N-1-5.1) to the formula (N-1-5.12)
  • the compounds represented by the formula (N-1-5.1), the formula (N-1-5.2) and the formula (N-1-5.4) are preferable.
  • the compounds represented by the formulas (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 preferred content of these compounds alone or in the total amount of the composition of the present invention is 5%, 8%, 10%, 13%, although it is also possible. It is 15%, 17% and 20%.
  • the upper limit value of the preferred content is 35%, 33%, 30%, 28%, 25%, 23%, or 35%, based on the total weight of the composition of the present invention. %, 18%, 15% and 13%.
  • the compounds represented by the general formula (N-1-10) are the following compounds.
  • R N 1101 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • R N 1102 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-10) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-10) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compound represented by General Formula (N-1-10) is a compound selected from the group of compounds represented by Formula (N-1-10.1) to Formula (N-1-10.14) And the compounds represented by formulas (N-1-10.1) to (N-1-10.5) are preferable, and the compounds represented by formulas (N-1-10.1) and (N- The compound represented by -1-10.2) is preferred.
  • the composition of the present invention can be used alone or in combination, the composition of the present invention
  • the lower limit value of the preferred content of these compounds alone or in the total amount of is 5%, 10%, 13%, 15%, 17%, 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-11) are the following compounds.
  • R N 1111 and R N 11 12 independently represents the same meaning as R N 11 and R N 12 in General Formula (N-1).
  • R N 1111 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.
  • R N 1112 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-11) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-11) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compound represented by General Formula (N-1-11) is a compound selected from the group of compounds represented by Formula (N-1-11.1) to Formula (N-1-11.14) And the compounds represented by formulas (N-1-11.1) to (N-1-11.14) are preferable.
  • the compound represented by 1-11.4) is preferable.
  • the composition of the present invention The lower limit value of the preferred content of these compounds alone or in the total amount of is 5%, 10%, 13%, 15%, 17%, 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-12) are the following compounds.
  • R N 1121 and R N1122 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • R N 1121 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • RN 1122 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-12) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-12) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-13) are the following compounds.
  • R N1131 and R N1132 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • R N 1131 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N 1132 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-13) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-13) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by General Formula (N-1-14) are the following compounds.
  • R N 1141 and R N 114 2 independently represents the same meaning as R N 11 and R N 12 in General Formula (N).
  • R N 1141 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • RN 1142 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-14) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-14) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-15) are the following compounds.
  • R N 1151 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N 1152 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-15) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-15) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by General Formula (N-1-16) are the following compounds.
  • R N 1161 and R N1162 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • R N 1161 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • R N 1162 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-16) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-16) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by General Formula (N-1-17) are the following compounds.
  • R N 1171 and R N1172 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • R N 1171 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • RN 1172 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-17) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-17) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-18) are the following compounds.
  • R N 1181 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably a methyl group, an ethyl group, a propyl group or a butyl group.
  • R N 1182 is preferably an alkyl group of 1 to 5 carbon atoms, an alkenyl group of 4 to 5 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compounds represented by General Formula (N-1-18) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-18) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compound represented by General Formula (N-1-18) is a compound selected from the group of compounds represented by Formula (N-1-18.1) to Formula (N-1-18.5) And the compounds represented by formulas (N-1-18.1) to (N-1-11.3) are preferable.
  • the compound represented by 1-18.3) is preferable.
  • the compounds represented by the general formula (N-1-20) are the following compounds.
  • R N1201 and R N1202 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • Each of R N1201 and R N1202 is independently preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • the compounds represented by General Formula (N-1-20) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-20) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by General Formula (N-1-21) are the following compounds.
  • each of R N 1211 and R N 12 12 independently represents the same meaning as R N 11 and R N 12 in general formula (N).
  • Each of R N1211 and R N1212 is independently preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • the compounds represented by General Formula (N-1-21) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-21) to the total amount of the composition of the present invention is 5%, 10%, 13%, 15% 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15% and 13%.
  • the compounds represented by the general formula (N-1-22) are the following compounds.
  • R N1221 and R N1222 independently represents the same meaning as R N11 and R N12 in the general formula (N).
  • Each of R N1221 and R N1222 is independently preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
  • the compounds represented by General Formula (N-1-22) can be used alone, but two or more compounds can also be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-22) to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17% and 20%.
  • the upper limit of the preferred content is 35%, 30%, 28%, 25%, 23%, 20%, or 35%, based on the total weight of the composition of the present invention. %, 15%, 13%, 10%, 5%.
  • the compound represented by General Formula (N-1-22) is a compound selected from the group of compounds represented by Formula (N-1-22.1) to Formula (N-1-22.12) Are preferably compounds represented by formulas (N-1-22.1) to (N-1-22.5), and compounds represented by formulas (N-1-22.1) to (N- The compound represented by 1-22.4) is preferable.
  • the compound represented by General Formula (N-3) is preferably a compound selected from the group of compounds represented by General Formula (N-3-2).
  • R N321 and R N322 each independently represents the same meaning as R N31 and R N32 in the general formula (N-3).
  • Each of R N321 and R N322 is preferably an alkyl group of 1 to 5 carbon atoms or an alkenyl group of 2 to 5 carbon atoms, and more preferably a propyl group or a pentyl group.
  • the compounds represented by General Formula (N-3-2) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (N-3-2) to the total amount of the composition of the present invention is 3%, 5%, 10%, 13% , 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%.
  • the upper limit of the preferred content is 50%, 40%, 38%, 35%, 33%, 30%, or 50%, based on the total weight of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 % And 5%.
  • the compound represented by General Formula (N-3-2) is a compound selected from the group of compounds represented by Formula (N-3-2.1) to Formula (N-3-2.3) Is preferred.
  • the liquid crystal composition of the present invention preferably contains one or two or more compounds represented by General Formula (L).
  • the compounds represented by the general formula (L) correspond to dielectric substantially neutral compounds (the value of ⁇ is ⁇ 2 to 2). Therefore, the number of polar groups such as halogen contained in the molecule is preferably 2 or less, more preferably 1 or less, and it is more preferable not to have one.
  • the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • n L1 is 2 or 3 and a plurality of A L2 is present, they may be the same or different, and when n L1 is 2 or 3 and a plurality of Z L2 is present, they may be Are the same as or different from each other, but the compounds represented by formulas (N-1), (N-2) and (N-3) are excluded.
  • the compounds represented by formula (L) may be used alone or in combination.
  • the types of compounds that can be combined but they are used in appropriate combination according to the desired performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of compound used is, for example, one type in one embodiment of the present invention. Or in another embodiment of the present invention, there are 2 types, 3 types, 4 types, 5 types, 5 types, 6 types, 7 types, 8 types, 9 types and 10 It is more than kind.
  • the content of the compound represented by the general formula (L) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L) to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit value of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.
  • the above lower limit is high and the upper limit is high. Furthermore, when the composition of the present invention is required to keep Tni high and a composition having good temperature stability is required, it is preferable that the above lower limit value is high and the upper limit value is high. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable that the above lower limit value be low and the upper limit value be low.
  • both R L1 and R L2 are preferably alkyl groups, and when importance is given to reducing the volatility of the compound, alkoxy groups are preferable, and viscosity reduction is important When doing, at least one is preferably an alkenyl group.
  • the number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3 and is preferably 0 or 1. When importance is attached to compatibility with other liquid crystal molecules, 1 is preferred.
  • R L1 and R L2 are, when the ring structure to which they are bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkyl group having 1 to 4 carbon atoms Alkoxy groups and alkenyl groups having 4 to 5 carbon atoms are preferred, and in the case where the ring structure to which they are attached is a saturated ring structure such as cyclohexane, pyran and dioxane, a straight chain having 1 to 5 carbon atoms is preferred.
  • An alkyl group, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferable.
  • the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in the ring structure.)
  • n L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferable to improve the upper limit temperature of the nematic phase, and 1 is preferable to balance them. Moreover, in order to satisfy the characteristics required as a composition, it is preferable to combine compounds of different values.
  • a L 1 , A L 2 and A L 3 are preferably aromatic when it is required to increase ⁇ n, and are preferably aliphatic to improve the response speed, and each of them is independently trans- 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group , 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferable, and the following structure is more preferable,
  • it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
  • Z L1 and Z L2 be a single bond when the response speed is important.
  • the compound represented by formula (L) preferably has 0 or 1 halogen atoms in the molecule.
  • the compound represented by formula (L) is preferably a compound selected from the group of compounds represented by formulas (L-1) to (L-7).
  • the compounds represented by formula (L-1) are the following compounds.
  • R L11 and R L12 each independently represent the same meaning as R L1 and R L2 in general formula (L).
  • R L11 and R L12 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, and linear alkenyl groups having 2 to 5 carbon atoms. .
  • the compounds represented by General Formula (L-1) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferred content is 1%, 2%, 3%, 5%, 7%, 10%, based on the total weight of the composition of the present invention. %, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%.
  • the upper limit of the preferred content is 95%, 90%, 85%, 80%, 75%, 70%, based on the total weight of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.
  • the above lower limit is high and the upper limit is high. Furthermore, when the composition of the present invention needs to have a high T ni and a composition having good temperature stability is required, it is preferable that the above lower limit value is medium and the upper limit value is medium. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable that the above lower limit value is low and the upper limit value is low.
  • the compound represented by General Formula (L-1) is preferably a compound selected from the group of compounds represented by General Formula (L-1-1).
  • the compound represented by General Formula (L-1-1) is a compound selected from the compound group represented by Formula (L-1-1.1) to Formula (L-1-1.3) It is preferable that it is a compound represented by the formula (L-1-1.2) or the formula (L-1-1.3), and in particular, it is represented by the formula (L-1-1.3) It is preferable that it is a compound.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-1.3) to the total amount of the composition of the present invention is 1%, 2%, 3%, It is 5%, 7% and 10%.
  • the upper limit of the preferred content is 20%, 15%, 13%, 10%, 8%, 7%, based on the total weight of the composition of the present invention. %, 5% and 3%.
  • the compound represented by General Formula (L-1) is preferably a compound selected from the group of compounds represented by General Formula (L-1-2).
  • R L12 has the same meaning as in the general formula (L-1).
  • the lower limit of the preferable content of the compound represented by the formula (L-1-2) to the total amount of the composition of the present invention is 1%, 5%, 10%, 15% , 17%, 20%, 23%, 25%, 27%, 30%, 35%.
  • the upper limit of the preferred content is 60%, 55%, 50%, 45%, 42%, 40%, based on the total weight of the composition of the present invention. %, 35%, 33%, and 30%.
  • the compound represented by General Formula (L-1-2) is a compound selected from the group of compounds represented by Formula (L-1-2.1) to Formula (L-1-2.4)
  • the compound is preferably a compound represented by Formula (L-1-2.2) to Formula (L-1-2.4).
  • the compounds represented by the formula (L-1-2.2) are preferable because they particularly improve the response speed of the composition of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-2.2) to the total amount of the composition of the present invention is 10%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40%.
  • the upper limit of the preferred content is 60%, 55%, 50%, 45%, 43%, 40%, 60%, based on the total weight of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, 22%.
  • Lower limit of preferable content of the total of the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) relative to the total amount of the composition of the present invention The values are 10%, 15%, 20%, 25%, 27%, 30%, 35%, 40%.
  • the upper limit of the preferred content is 60%, 55%, 50%, 45%, 43%, 40%, 60%, based on the total weight of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, 22%.
  • the compound represented by formula (L-1) is preferably a compound selected from the group of compounds represented by formula (L-1-3).
  • L L13 and R L14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • R L13 and R L14 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, and linear alkenyl groups having 2 to 5 carbon atoms. .
  • the lower limit of the preferable content of the compound represented by the formula (L-1-3) to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% , 15%, 17%, 20%, 23%, 25%, 30%.
  • the upper limit of the preferred content is 60%, 55%, 50%, 45%, 40%, 37%, 35%, based on the total weight of the composition of the present invention. %, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10%. %.
  • the compound represented by General Formula (L-1-3) is a compound selected from the group of compounds represented by Formula (L-1-3.1) to Formula (L-1-3.13)
  • the compound is preferably a compound represented by formula (L-1-3.1), formula (L-1-3.3) or formula (L-1-3.4).
  • the compound represented by the formula (L-1-3.1) is preferable in order to particularly improve the response speed of the composition of the present invention.
  • the formula (L-1-3.4), the formula (L-1-3.11) and formula (L It is preferable to use a compound represented by the formula -1-3.12).
  • the lower limit of the preferable content of the compound represented by the formula (L-1-3.1) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20%.
  • the upper limit of the preferred content is 20%, 17%, 15%, 13%, 10%, 8%, or 20%, based on the total weight of the composition of the present invention. % And 6%.
  • the compound represented by Formula (L-1) is preferably a compound selected from the group of compounds represented by Formula (L-1-4) and / or (L-1-5).
  • R L15 and R L16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • R L15 and R L16 are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, and linear alkenyl groups having 2 to 5 carbon atoms. .
  • the lower limit of the preferable content of the compound represented by the formula (L-1-4) to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17% and 20%.
  • the upper limit of the preferred content is 25%, 23%, 20%, 17%, 15%, 13%, 10%, based on the total weight of the composition of the present invention. %.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-5) to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17% and 20%.
  • the upper limit of the preferred content is 25%, 23%, 20%, 17%, 15%, 13%, 10%, based on the total weight of the composition of the present invention. %.
  • compounds represented by general formulas (L-1-4) and (L-1-5) are represented by formulas (L-1-4.1) to (L-1-5.3) It is preferable that it is a compound selected from the group of compounds, and it is preferable that it is a compound represented by Formula (L-1-4.2) or Formula (L-1-5.2).
  • the lower limit of the preferable content of the compound represented by the formula (L-1-4.2) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20%.
  • the upper limit of the preferred content is 20%, 17%, 15%, 13%, 10%, 8%, or 20%, based on the total weight of the composition of the present invention. % And 6%.
  • R L17 and R L18 each independently represent a methyl group or a hydrogen atom.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-6) to the total amount of the composition of the present invention is 1%, 5%, 10%, 15% , 17%, 20%, 23%, 25%, 27%, 30%, 35%.
  • the upper limit of the preferred content is 60%, 55%, 50%, 45%, 42%, 40%, based on the total weight of the composition of the present invention. %, 35%, 33%, and 30%.
  • the compound represented by General Formula (L-1-6) is a compound selected from the group of compounds represented by Formula (L-1-6.1) to Formula (L-1-6.3) Is preferred.
  • the compounds represented by formula (L-2) are the following compounds.
  • R L21 and R L22 each independently represent the same meaning as R L1 and R L2 in general formula (L).
  • R L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L22 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom
  • the alkoxy groups of 1 to 4 are preferable.
  • the compounds represented by General Formula (L-2) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (L-2) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7% and 10%.
  • the upper limit of the preferred content is 20%, 15%, 13%, 10%, 8%, 7%, based on the total weight of the composition of the present invention. %, 5% and 3%.
  • the compound represented by General Formula (L-2) is preferably a compound selected from the group of compounds represented by Formula (L-2.1) to Formula (L-2.6), Compounds represented by (L-2.1), formula (L-2.3), formula (L-2.4) and formula (L-2.6) are preferable.
  • the compounds represented by formula (L-3) are the following compounds.
  • R L31 and R L32 each independently represent the same meaning as R L1 and R L2 in general formula (L).
  • R L31 and R L32 are preferably each 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 formula (L-3) can be used alone or in combination of two or more. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (L-3) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7% and 10%.
  • the upper limit of the preferred content is 20%, 15%, 13%, 10%, 8%, 7%, based on the total weight of the composition of the present invention. %, 5% and 3%.
  • the compound represented by General Formula (L-3) is preferably a compound selected from the group of compounds represented by Formula (L-3.1) to Formula (L-3.7), Compounds represented by (L-3.2) to (L-3.5) are preferable.
  • the compounds represented by formula (L-4) are the following compounds.
  • R L41 and R L42 each independently represent the same meaning as R L1 and R L2 in General Formula (L).
  • R L41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L42 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom
  • the alkoxy groups of 1 to 4 are preferable.
  • the compounds represented by formula (L-4) can be used alone or in combination of two or more compounds.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-4) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, It is necessary to appropriately adjust according to the required performance such as burn-in and dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L-4) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% .
  • the upper limit of the preferable content of the compound represented by the formula (L-4) to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. 20%, 15%, 10% and 5%.
  • the compound represented by General Formula (L-4) is preferably a compound represented by Formula (L-4.1) to Formula (L-4.3), for example.
  • the compound represented by the formula (L-4.1) can be represented by the formula (L-4.1) Even if it contains the compound represented by -4.2), it contains 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 Formula (L-4.1) to Formula (L-4.3) may be contained.
  • the lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) to the total amount of the composition of the present invention is 3%, 5% Yes, 7%, 9%, 11%, 12%, 13%, 18%, 21%, preferred upper limit is 45, 40% , 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% .
  • both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, both compounds relative to the total amount of the composition of the present invention
  • the lower limit of the preferable content is 15%, 19%, 24%, 30%, and the preferable upper limit is 45, 40%, 35%, 30% Yes, 25%, 23%, 20%, 18%, 15%, 13%.
  • the compound represented by General Formula (L-4) is preferably a compound represented by Formula (L-4.4) to Formula (L-4.6), for example. It is preferable that it is a compound represented by these.
  • the compound represented by the formula (L-4.4) may be represented by the formula (L-4.4) Even if it contains the compound represented by -4.5), it contains both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) May be
  • the lower limit of the preferable content of the compound represented by the formula (L-4.4) or the formula (L-4.5) to the total amount of the composition of the present invention is 3%, 5% Yes, 7%, 9%, 11%, 12%, 13%, 18%, 21%.
  • the preferred upper limit is 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%. %, 10%, and 8%.
  • both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, both compounds relative to the total amount of the composition of the present invention
  • the lower limit of the preferable content is 15%, 19%, 24%, 30%, and the preferable upper limit is 45, 40%, 35%, 30% Yes, 25%, 23%, 20%, 18%, 15%, 13%.
  • the compound represented by Formula (L-4) is preferably a compound represented by Formula (L-4.7) to Formula (L-4.10), and in particular, a compound represented by Formula (L-4.
  • the compound represented by 9) is preferable.
  • the compounds represented by General Formula (L-5) are the following compounds.
  • R L51 and R L52 each independently represent the same meaning as R L1 and R L2 in general formula (L).
  • R L51 is preferably an alkyl group or an alkenyl group having 2 to 5 carbon atoms having 1 to 5 carbon atoms
  • R L52 is an alkyl group, an alkenyl group or a carbon atom of the carbon atoms 4-5 of 1-5 carbon atoms
  • the alkoxy groups of 1 to 4 are preferable.
  • the compounds represented by General Formula (L-5) can be used alone, or two or more compounds can be used in combination. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-5) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, It is necessary to appropriately adjust according to the required performance such as burn-in and dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L-5) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% .
  • the upper limit of the preferable content of the compound represented by the formula (L-5) to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. 20%, 15%, 10% and 5%
  • the compound represented by the general formula (L-5) is a compound represented by the formula (L-5.1) or the formula (L-5.2) It is preferable that it is a compound represented by these, and it is especially preferable that it is a compound represented by Formula (L-5.1).
  • the lower limit value of the preferable content of these compounds to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%.
  • the upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.
  • the compound represented by General Formula (L-5) is preferably a compound represented by Formula (L-5.3) or Formula (L-5.4).
  • the lower limit value of the preferable content of these compounds to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%.
  • the upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.
  • the compound represented by General Formula (L-5) is preferably a compound selected from the group of compounds represented by Formula (L-5.5) to Formula (L-5.7), and in particular It is preferable that it is a compound represented by L-5.7).
  • the lower limit value of the preferable content of these compounds to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%.
  • the upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.
  • the compounds represented by General Formula (L-6) are the following compounds.
  • R L61 and R L62 each independently represent the same as R L1 and R L2 in General Formula (L), and X L61 and X L62 each independently represent a hydrogen atom or a fluorine atom.
  • Each of R L61 and R L62 is preferably independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of X L61 and X L62 is a fluorine atom, and the other is a hydrogen atom Is preferred.
  • the compounds represented by formula (L-6) can be used alone or in combination of two or more compounds. There is no particular limitation on the types of compounds that can be combined, but they are used in appropriate combination according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence and the like.
  • the type of the compound used is, for example, one type, two types, three types, four types, five types or more as one embodiment of the present invention.
  • the lower limit of the preferable content of the compound represented by the formula (L-6) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% .
  • the upper limit of the preferable content of the compound represented by the formula (L-6) to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. 20%, 15%, 10% and 5%.
  • the compound represented by General Formula (L-6) is preferably a compound represented by Formula (L-6.1) to Formula (L-6.9).
  • the compound represented by General Formula (L-6) is preferably a compound represented by Formula (L-6.10) to Formula (L-6.17), for example.
  • the compound represented by L-6.11) is preferred.
  • the lower limit value of the preferable content of these compounds to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%.
  • the upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.
  • the compounds represented by General Formula (L-7) are the following compounds.
  • R L71 and R L72 each independently represent the same as R L1 and R L2 in the general formula (L), and A L71 and A L72 are each independently A L2 and A L2 in the general formula (L)
  • a hydrogen having the same meaning as A L3 is represented, but each of hydrogen atoms on A L71 and A L72 may be independently substituted by a fluorine atom
  • Z L71 has the same meaning as Z L2 in formula (L)
  • X L71 and X L72 each independently represent a fluorine atom or a hydrogen atom.
  • R L71 and R L72 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms of 2 to 5 carbon atoms preferably
  • a L71 and A L72 each independently 1,4-cyclohexylene group or a 1,4-phenylene group is preferably a hydrogen atom on a L71 and a L72 may be substituted by fluorine
  • the type of compound used is, for example, one type, two types, three types, and four types according to one embodiment of the present invention.
  • the content of the compound represented by the general formula (L-7) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping mark, It is necessary to appropriately adjust according to the required performance such as burn-in and dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L-7) to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 14%, 16% and 20%.
  • the upper limit of the preferable content of the compound represented by the formula (L-7) to the total amount of the composition of the present invention is 30%, 25%, 23%, and 20%. 18%, 15%, 10% and 5%.
  • the compound represented by General Formula (L-7) is preferably a compound represented by Formula (L-7.1) to Formula (L-7.4), and Formula (L-7. It is preferable that it is a compound represented by 2).
  • the compound represented by General Formula (L-7) is preferably a compound represented by Formula (L-7.11) to Formula (L-7.13), and the compound represented by Formula (L-7. It is preferable that it is a compound represented by 11).
  • the compound represented by General Formula (L-7) is a compound represented by Formula (L-7.21) to Formula (L-7.23). It is preferable that it is a compound represented by Formula (L-7.21).
  • the compound represented by General Formula (L-7) is preferably a compound represented by Formula (L-7. 31) to Formula (L-7. 34), and the compound represented by Formula (L-7. 31) or / and a compound represented by the formula (L-7. 32) is preferable.
  • the compound represented by General Formula (L-7) is preferably a compound represented by Formula (L-7.41) to Formula (L-7.44), and the compound represented by Formula (L-7. 41) or / and a compound represented by the formula (L-7. 42) is preferable.
  • the compound represented by General Formula (L-7) is preferably a compound represented by Formula (L-7.51) to Formula (L-7.53).
  • the lower limit of the preferable content of the total of the compounds represented by general formula (i), general formulas (L) and (N) with respect to the total amount of the composition of the present invention is 80%, 85% Yes, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% Yes, 100%.
  • the upper limit of the preferred content is 100%, 99%, 98% and 95%.
  • the lower limit of the preferable content of the total of the compounds represented by general formula (i) and general formulas (L-1) to (L-7) relative to the total amount of the composition of the present invention is 80% , 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98% , 99% and 100%.
  • the upper limit of the preferred content is 100%, 99%, 98% and 95%.
  • composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms such as a peracid (—CO—OO—) structure are bonded to each other in the molecule.
  • the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, based on the total mass of the composition. Preferably, it is more preferably 1% or less, and most preferably substantially free.
  • the content of the compound substituted with chlorine atoms is preferably 15% or less, preferably 10% or less, based on the total mass of the composition. % Is preferable, 5% or less is more preferable, 3% or less is preferable, and substantially no content is further preferable.
  • the content of compounds in which all ring structures in the molecule are six-membered rings is 80 based on the total mass of the composition. % Or more is preferable, 90% or more is more preferable, 95% or more is more preferable, and the composition is composed only of compounds in which all ring structures in the molecule are substantially 6-membered rings. Most preferred.
  • the content of the compound having a cyclohexenylene group is the total mass of the composition.
  • it is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and even more preferably substantially non-containing.
  • the content of a compound having a 2-methylbenzene-1,4-diyl group in which the hydrogen atom may be substituted by halogen in the molecule should be reduced.
  • the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% or less, and more preferably 8% or less based on the total mass of the composition.
  • the content is preferably 5% or less, more preferably 3% or less, and even more preferably substantially non-containing.
  • not substantially contained means that it is not contained except for unintentionally contained substances.
  • the number of carbon atoms of the alkenyl group is 2 to 5
  • the number of carbon atoms of the alkenyl group is preferably 4 to 5, and the unsaturated bond of the alkenyl group and benzene are directly bonded. Preferably not.
  • the average elastic constant (K AVG ) of the liquid crystal composition used in the present invention is preferably 10 to 25, but the lower limit is preferably 10, 10.5 is preferred, 11 is preferred and 11.5 is preferred.
  • 12 is preferable, 12.3 is preferable, 12.5 is preferable, 12.8 is preferable, 13 is preferable, 13.3 is preferable, 13.5 is preferable, 13.8 is preferable, 14 is preferable, 14 3 is preferable, 14.5 is preferable, 14.8 is preferable, 15 is preferable, 15.3 is preferable, 15.5 is preferable, 15.8 is preferable, 16 is preferable, 16.3 is preferable, 16 5 is preferable, 16.8 is preferable, 17 is preferable, 17.3 is preferable, 17.5 is preferable, 17.8 is preferable, and 18 is preferable, and the upper limit thereof is 25 is preferable, 24.5 is preferable, 24 is preferable, 23.5 is preferable, 23 is preferable, 22.8 is preferable, 22.5 is preferable, 22.3 is preferable, 22 is preferable, 21.8 is 2
  • K AVG When importance is given to reducing power consumption, it is effective to reduce the amount of light from the backlight, and it is preferable to improve the light transmittance of the liquid crystal display element. For that purpose, the value of K AVG should be set lower. preferable. When emphasis is placed on improvement of response speed, it is preferable to set the value of K AVG higher.
  • the polymerizable liquid crystal composition according to the present invention preferably contains a spontaneous alignment compound.
  • the spontaneous orientation compound is a compound that controls the orientation of the liquid crystal composition without using a conventional liquid crystal alignment film such as polyimide for one or both of the substrates.
  • the spontaneous orientation compound is mainly added to the liquid crystal composition and used, and a member (for example, ITO) directly in contact with the liquid crystal layer containing the liquid crystal composition, a substrate (for example, a glass substrate, an acrylic substrate, a transparent substrate , A flexible substrate, etc.), a resin layer (eg, color filter, alignment film, overcoat layer), an insulating film (eg, inorganic material film, It has a function of inducing tropic alignment or homogeneous orientation.
  • a compound capable of orienting the liquid crystal composition vertically or almost perpendicularly to the substrate is preferable.
  • the spontaneously orienting compound includes a polymerizable group for polymerization, a mesogenic group similar to liquid crystal molecules, an adsorptive group capable of interacting with a member in direct contact with the liquid crystal layer, and a bending group for inducing the alignment of the liquid crystal molecules. It is preferable to have.
  • the spontaneously orienting compound is preferably a compound represented by the following general formula (SAL).
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms
  • W p11 is a single bond, —O -, -COO- or a methylene group
  • p and t p11 each independently represent 0, 1 or 2.
  • MG represents a mesogenic group
  • Cg represents a hydrogen atom, an adsorptive group, an alkylene group -Sp al -P al
  • P al is a group selected from the group represented by general formula (PI) to general formula (P-IX) below, and is more preferably general formula (PI). .
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, and W p11 is a single bond, —O -, -COO- or a methylene group, p and t p11 represent 0, 1 or 2.
  • P al -Sp al - it is mesogenic groups may be bonded to an adsorptive group and / or bending group.
  • the polymerizable group is preferably bonded to the mesogenic group, the adsorptive group or the bending group directly or via a spacer group, and the direct bond to the mesogenic group or the adsorptive group Or it is more preferable to couple
  • P al -Sp al - hydrogen atoms in the polymerizable group may be substituted with an adsorptive group and / or bending group.
  • the mesogenic group according to the present invention refers to a group having a rigid portion, for example, one having one or more cyclic groups, and preferably has 2 to 4 cyclic groups, and is preferably a cyclic group. Is more preferably 3 to 4. If necessary, the cyclic group may be linked by a linking group.
  • the mesogenic group is preferably a skeleton similar to the liquid crystal compound used in the liquid crystal layer.
  • cyclic group refers to an atomic group in which the constituting atoms are cyclically bound, and includes a carbocyclic ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a single ring, a bicyclic structure and a polycyclic ring. Including formula structures, aromatics, non-aromatics, etc. Also, the cyclic group may contain at least one hetero atom, and may be further substituted by at least one substituent (halogen atom, reactive functional group, organic group (alkyl, aryl etc.). When the group is a single ring, the mesogenic group preferably contains two or more single rings.
  • the said mesogenic group is represented, for example by General formula (AL).
  • a AL represents a divalent cyclic group, One or
  • Z AL is preferably a single bond or an alkylene group having 2 to 20 carbon atoms, and more preferably a single bond or an alkylene group having 2 to 10 carbon atoms.
  • One or two or more non-adjacent —CH 2 — in the alkylene group may be substituted with —O—, —COO— or —OCO—.
  • the number of the single bond which is a form in which a ring and a ring are directly connected and the number of atoms directly connecting the ring and the ring is an even number. For example, in the case of —CH 2 —CH 2 COO—, the number of atoms directly linking the ring to the ring is four.
  • the cyclic group that A AL can adopt is 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, thiophene-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydro Naphthalene-2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1, 2, 3,4-Tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene
  • a monovalent organic group is a group having a chemical structure constituted by the organic compound being in the form of a monovalent group, and is formed by removing one hydrogen atom from the organic compound.
  • an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkenyloxy group having 2 to 15 carbon atoms, etc. Preferred is an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms.
  • one or two or more non-adjacent —CH 2 — in the alkyl group, the alkenyl group, the alkoxy group and the alkenyloxy group may be substituted by —O—, —COO— or —OCO—.
  • the monovalent organic group may have a role as a bending group described later.
  • m AL is preferably an integer of 2 to 4.
  • Formula (AL-1) a particularly preferred form is represented by the following Formula (AL-1) or (AL-2), and Formula (AL-1) is more preferred.
  • X al1 ⁇ X al18 are each independently a hydrogen atom, a halogen atom, P al -Sp al -, represents an adsorption group or bend group
  • ring A and ring B are each independently a cyclohexane ring Or a benzene ring
  • One or more of X al1 to X al 18 are substituted with the above-mentioned adsorptive group
  • One or more kinds of X al1 to X al18 are substituted with the above-mentioned bending group
  • the adsorptive group and said bending group wherein P al -Sp al - may be substituted with
  • Each of the general formula (AL-1) and the general formula (AL-2) has one or more of P al -S al- .
  • X Al9 or X AL11 is P al -Sp al of X al6 ⁇ X al14 More preferably, it is substituted by-.
  • X al1 to X al3 , X al6 to X al14 , and X al17 to X al18 be substituted with a bending group
  • X al1 to X It is preferable that at least one or more of al 3 , X al 6 to X al 9 , X al 11 to X al 14 or X al 17 to X al 18 be substituted with a bending group. More preferably, X al1 is substituted with a bending group, and any one of X al6 to X al9 or X al11 to X al14 is substituted with a bending group. In this case, towards the bending groups in the former X AL1 it is it is more preferably a large number of carbon atoms than the latter bending group.
  • the bending group may be substituted by P al -S al- .
  • X al1 or X al6 to X al 10 be substituted with an adsorptive group
  • X al1 or X al8 be substituted with an adsorptive group Is more preferred.
  • the adsorptive group may be substituted by P al -S al- .
  • ring A is a cyclohexane ring
  • X al 8 be substituted with an adsorptive group.
  • At least one or two or more P al -Sp al of X al6 ⁇ X al10 - is preferably substituted in either one of X AL7 or X AL4 is P al it is more preferably substituted in the - -sp al.
  • Examples of the preferred form of the mesogen group include the following formulas (AL-1-1) to (AL-2-3).
  • General formula (AL) is a structure where two hydrogen atoms in these structures are eliminated.
  • One or more of hydrogen atoms in a cyclohexane ring, a benzene ring, a pyran ring or a dioxane ring in any of the general formulas (AL-1-1) to (AL-2-3) are a halogen atom, P al ⁇ It may be substituted by Sp al- , a monovalent organic group (eg, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms), an adsorptive group or a bending group.
  • preferred embodiments are the general formula (AL-1-1), the general formula (AL-1-4), the general formula (AL-1-7), the general formula (AL-2-1) or the general formula A structure represented by formula (AL-2-3), which is represented by a general formula (AL-1-4), a general formula (AL-1-7) or a general formula (AL-2-3); And a structure represented by formula (AL-1-4) or (AL-1-7).
  • the adsorbing group according to the present invention is a group having a function of adsorbing to an adsorbent such as a substrate, a film, an electrode and the like.
  • Adsorption is generally separated into chemical adsorption in which a chemical bond (covalent bond, ionic bond or metal bond) is formed to be adsorbed between an adsorbent and an adsorbate, or physical adsorption other than the chemical adsorption.
  • the adsorption of the paper may be either chemical adsorption or physical adsorption, but it is preferable to adsorb with the adsorbent by physical adsorption.
  • the adsorptive group according to the present invention is preferably a group capable of physically adsorbing to the adsorbent, and the adsorptive group is more preferably bonded to the adsorbent by an intermolecular force.
  • bonded with an adsorbent by the said intermolecular force it has couple
  • the adsorptive group according to the present invention may be a donor or acceptor of a proton that mediates a hydrogen bond, or both.
  • the adsorptive group according to the present invention is preferably a group containing a polar element having an atomic group in which a carbon atom and a hetero atom are linked.
  • the polar element as used herein means an atomic group in which a carbon atom and a hetero atom are directly linked.
  • the hetero atom is preferably at least one selected from the group consisting of N, O, S, P, B and Si, and is at least one selected from the group consisting of N, O and S. Is preferable, and at least one selected from the group consisting of N and O is preferable, and O is preferable.
  • the valence of the polar element according to the present invention is not particularly limited, such as monovalent, divalent or trivalent, and the number of polar elements in the adsorptive group is also particularly limited. There is nothing to do.
  • the number of the adsorption groups is preferably 1 to 8, more preferably 1 to 4, and still more preferably 1 to 3, in one molecule.
  • the adsorption group according to the present invention P al -Sp al - and bent groups are excluded.
  • the adsorptive group according to the present invention contains one or more polar elements, and the adsorptive group is roughly classified into cyclic group type and chain group type.
  • a cyclic group type is a form that includes a cyclic group with a cyclic structure that includes a polar element in its structure
  • a chain group type includes a cyclic group that includes a cyclic structure that includes a polar element in its structure.
  • the chain group is a form having a polar element in a linear or branched chain group, and a part thereof may have a cyclic structure not containing a polar element.
  • the form in which the adsorptive group according to the present invention contains a cyclic group means a form in which at least one polar element is contained in a cyclic atomic arrangement.
  • the cyclic group in the present specification is as described above. Therefore, in the case where the adsorptive group according to the present invention contains a cyclic group, it only needs to contain a cyclic group containing a polar element, and the entire adsorptive group may be branched or linear. .
  • the adsorptive group according to the present invention is in the form of a chain group in that there is no cyclic atomic arrangement containing polar elements in the molecule, and at least one polar element can be linear (possibly branched) It means the form included.
  • chain group refers to an atomic group in which structural atoms have no linear atomic arrangement in the structural formula and in which the constituting atoms are linearly (or may be branched) bonded, and an acyclic group. .
  • a linear or branched aliphatic group which may contain either a saturated bond or an unsaturated bond, including, for example, alkyl, alkenyl, alkoxy, ester, ether or ketone, etc., at least one It is a concept which may be substituted by a substituent (reactive functional group (vinyl group, acryl group, methacryl group, etc.), chain organic group (alkyl, cyano, etc.). It may be linear or branched.
  • the adsorptive group according to the present invention preferably has a chain group or a cyclic group.
  • a chain group is preferable, and a cyclic group is preferable from the viewpoint of the stability to the liquid crystal composition.
  • the adsorptive group according to the present invention is a cyclic group, it has a heteroaromatic group having 3 to 20 carbon atoms (including a fused ring) or a heteroaliphatic group having 3 to 20 carbon atoms (including a fused ring) Is more preferable, a C 3-12 heteroaromatic group (including a fused ring) or a C 3-12 heteroaliphatic group (including a fused ring) is more preferable, and a 5-membered ring complex is more preferable.
  • it represents an aromatic group, a 5-membered ring heteroaliphatic group, a 6-membered ring heteroaromatic group or a 6-membered ring heteroaliphatic group, and the hydrogen atom in these ring structures is a halogen atom, the number of carbon atoms It may be substituted by 1 to 5 linear or branched alkyl groups or alkyloxy groups.
  • the adsorptive group according to the present invention is a chain group
  • a hydrogen atom or -CH 2 -in a linear or branched alkyl group having 1 to 20 carbon atoms be substituted by a polar element
  • the end portion contains a polar element or contains two or more polar elements.
  • the hydrogen atom of the adsorptive group according to the present invention may be substituted by a polymerizable group.
  • the type of polar element according to the present invention includes an oxygen atom-containing polar element (hereinafter, oxygen-containing polar element), a nitrogen atom-containing polar element (hereinafter, nitrogen-containing polar element), and a phosphorus atom Element (hereinafter, phosphorus-containing polar element), polar element including boron atom (hereinafter, boron-containing polar element), polar element including silicon atom (hereinafter, silicon-containing polar element) or polar element including sulfur atom (hereinafter, including It is preferable that it is a partial structure represented by (sulfur polar element), and from the viewpoint of adsorption capacity, nitrogen-containing polar element, nitrogen-containing polar element or oxygen-containing polar element is more preferable, and oxygen-containing polar element is even more preferable.
  • oxygen-containing polar element hereinafter, oxygen-containing polar element
  • nitrogen-containing polar element or oxygen-containing polar element is more preferable
  • oxygen-containing polar element is even more prefer
  • cyano group (-CN), primary amino group (-NH 2 ), secondary amino group (-NH-), tertiary amino group (-NRR '; however, R, R' Is at least one group selected from the group consisting of an alkyl group), pyridyl group, carbamoyl group (-CONH 2 ) and ureido group (-NHCONH 2 ), or a group in which the group is linked to a carbon atom Is preferred.
  • the boron-containing polar element is preferably a group in which a boric acid group (—B (OH) 2 ) is linked to a carbon atom.
  • silicon-containing polar element -Si (OH) 3 group or -Si (OR) (OR ') (OR''); provided that R, R' and R '' are alkyl groups, and the carbon atom is It is preferable that it is a connected group.
  • the adsorptive group according to the present invention is a group in which the cyclic group has an oxygen-containing polar element (hereinafter, an oxygen-containing cyclic group) and a group in which the cyclic group has a nitrogen atom polar element (hereinafter, a nitrogen-containing ring Formula group), a group in which the cyclic group has a phosphorus-containing polar element (hereinafter referred to as a phosphorus-containing cyclic group), a group in which the cyclic group has a boron-containing polar element (hereinafter referred to as a boron-containing cyclic group), cyclic A group having a silicon-containing polar element (hereinafter, a silicon-containing cyclic group), a group having a sulfur group containing a sulfur-containing polar element (hereinafter, a sulfur-containing cyclic group), a chain group having an oxygen-containing polar element (Hereinafter referred to as an oxygen-containing chain group), a chain
  • the above oxygen-containing cyclic group preferably has an ether group or a carbonyl group in the ring, and the ether group preferably contains the following groups.
  • the carbonyl group preferably contains any of the following groups.
  • the nitrogen-containing cyclic group preferably contains any of the following groups.
  • the above sulfur-containing cyclic group preferably contains any of the following groups.
  • the above-mentioned boron-containing cyclic group preferably contains any of the following groups.
  • the silicon-containing cyclic group preferably contains a silsesquioxane group [-(R) n (SiO 1.5 ) n-1 ].
  • the above oxygen-containing chain group preferably contains any of the following groups.
  • the above-mentioned nitrogen-containing chain group preferably contains the following groups.
  • R at , R bt , R ct and R dt each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the above-mentioned sulfur-containing chain group preferably contains the following groups.
  • the silicon-containing chain group preferably contains —Si (OH) 3 or —Si (OR) (OR ′) (OR ′ ′), provided that R, R ′, R ′ ′ is an alkyl group).
  • the boron-containing chain group preferably contains -B (OH) 2 .
  • Z t1 represents the eight linear or branched alkylene group or Z t1 carbon atoms which may be coupled with 2 to 8 linear or branched alkenylene group
  • Z t1 represents a single bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms
  • -, -OCO- may be substituted,
  • n t1 represents an integer of 0 or more and 4 or less, Hydrogen atoms in the molecule a polymerizable group P al -Sp al - (.
  • P al and Sp al are the same as P al and Sp al in the above general formula (SAL)) may be substituted by, * the binding It represents a hand and is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • preferable X t1 represents a linear or branched alkyl group having 1 to 17 carbon atoms, -NH 2 or -Z t2 -O-R t1 group, and the alkyl group hydrogen atom a cyano group in, P al -Sp al - may be substituted by the above R t1 represents a hydrogen atom, a carbon atom bonded to an alkyl group or Z t1 of 1 to 5 carbon atoms 1 to represent the eight linear or branched alkylene group or Z t1 carbon atoms which may be coupled with 2 to 8 linear or branched alkenylene group, the Z t2 are single Represents a bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms, and the alkylene group or —CH 2 of the corresponding alkenylene group 2 - is directly adjacent oxygen
  • the hydrogen atom of the alkylene group represented by W t0 may be substituted by the general formula (T), in other words, the adsorptive group (general formula (T)) is the adsorptive group (general formula (T) As a form which may be substituted by T), the said general formula (T) is group represented with the following general formula (t) is mentioned.
  • X t1, Z t1, W t1 and n t1 is the same as X t1, Z t1, W t1 and n t1 in the above general formula (T)
  • W t2 represents a single bond or a divalent to tetravalent organic group
  • m t1 represents an integer of 1 to 3
  • P al -Sp al - P al and Sp al are the same as P al and Sp al in the above general formula (SAL)
  • * represents a bond, which is bonded to a mesogen group, a polymerizable group, a bending group or a spacer group.
  • “-W t2 -Any” in the general formula (t) indicates that W t2 represents a single bond to a multivalent group, and the bond is monovalent to multivalent (Any).
  • a divalent to tetravalent organic group is a group having a chemical structure constituted by the organic compound being in the form of a divalent to tetravalent group, and from the organic compound to a hydrogen atom Refers to an atomic group formed by removing two to four.
  • a divalent to tetravalent organic group -W t2 -Any is preferably a chain organic group, and, for example, a linear or branched C1 to C10 carbon atoms
  • the alkylene multivalent group is a trivalent or tetravalent group formed by removing one or two hydrogen atoms from the alkylene group, and a trivalent to tetravalent group having a free valence in a so-called hydrocarbon chain.
  • the group represented by the above general formula (t) is a preferred embodiment of W t0 in the general formula (T), that is, even though the adsorptive group (general formula (T)) is substituted by the adsorptive group (general formula (T))
  • W t2 is a trivalent organic group, ie, m t1 is 2 and W t2 is nitrogen
  • W ta is an atom or an alkylene polyvalent group
  • the following general formula (ta) or (tb) may be mentioned.
  • R tc represents a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or a polymerizable group P al -S al- Represented by Z t1 and Z t1 ′ independently represent the same meaning as Z t1 in the general formula (T), X t1 and X t1 ′ independently represent the same meaning as X t1 in the general formula (T), W t1 represents the same meaning as W t1 in the general formula (T), n t1 and n t1 ′ independently represent the same meaning as n t1 in the general formula (T), Hydrogen atoms in the molecule a polymerizable group P al -Sp al - (.
  • P al and Sp al are the same as P al and Sp al in the above general formula (SAL)) may be substituted by, * the binding It represents a hand and is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • the general formula (t) for example, when -W t2 -Any is a tetravalent organic group, that is, when m t1 is 3 and -W t2 -Any is an alkylene multivalent group, for example, t-c).
  • Z t1 , Z t1 ′ and Z t1 ′ ′ each independently represent the same meaning as Z t1 in the general formula (T)
  • X t1 , X t1 ′ and X t1 ′ ′ each independently represent the same meaning as X t1 in the general formula (T)
  • W t1 represents the same meaning as W t1 in the general formula (T)
  • the hydrogen atoms in the molecule a polymerizable group P al -Sp al - P al and Sp al are the same as P al and Sp al in the above general formula (SAL).
  • * represents a bond, bond and mesogenic groups, polymerizable groups, the bending group or spacer group Do.
  • m t1 is preferably 1 or 2, and more preferably 1. Further, among the embodiments represented by the above general formula (ta), general formula (tb) and general formula (tc), the embodiment represented by the above general formula (ta) is preferable .
  • -W t2 -Any is preferably a single bond or a divalent to trivalent organic group, and is a single bond or a linear or branched alkylene group having 1 to 8 carbon atoms
  • the —CH 2 — of the alkylene group may be substituted by —O— so that the oxygen atom is not directly adjacent to it, a linear or branched alkanetriyl group having 1 to 8 carbon atoms
  • the —CH 2 — of the alkanetriyl group may be substituted by —O— so that the oxygen atom is not directly adjacent to it, or a linear or branched alkyl-ylidene group (—CH of the alkyl-ylidene group concerned) 2- is more preferably -O- such that the oxygen atom is not directly adjacent.
  • the following groups may be mentioned.
  • R tc is C 1 -C 8 alkyl group or a polymerizable group P al -Sp al - (P al and Sp al are the same as P al and Sp al in the above general formula (SAL) . in a) represents, n t0 is an integer of 1-7, * represents a bond) Further, W t2 of the hydrogen atoms in the polymerizable group P al -Sp al -. may be substituted .
  • m t1 preferably represents 1 or 2.
  • W t1 may be substituted for and bonded to a hydrogen atom of a mesogenic group, a polymerizable group or a bending group.
  • the general formula (T) or the general formula (t) is, X t1 is a form that does not bind to the Z t1 (Kusarishikimoto), X t1 to form a ring with Z t1 forms (cyclic group) And contains.
  • X t1 is the number of carbon atoms substituted by a linear or branched alkyl group having 1 to 8 carbon atoms, -NH 2 , -Z t2 -O-R t1 group or cyano group 1 to 7 linear or branched alkyl group is preferable, and is substituted by a linear or branched alkyl group having 1 to 7 carbon atoms, -Z t2 -O-R t1 group, cyano group More preferred is a linear or branched alkyl group having 1 to 7 carbon atoms.
  • -Z t2 -O-R t1 groups R t1 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, Z t2 is a single bond, a carbon atom
  • n t1 is 1 or more
  • X t1 is -Z t2 -O-R t1
  • R t1 is a linear or branched alkylene group having 1 to 7 carbon atoms or the number of carbon atoms a 2-7 straight-chain or branched alkenylene group
  • substituted to the hydrogen atom of Z t1 binds R t1, for example, be represented by the following general formula (T ') Is preferred.
  • R t1 ′ each independently represents a linear or branched alkylene group having 1 to 8 carbon atoms, or a linear or branched chain having 2 to 8 carbon atoms Represents an alkenylene group
  • Z t2 ' each independently represents a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkenylene group having 2 to 10 carbon atoms
  • W t2 represents a single bond or a divalent to tetravalent organic group
  • W t1 represents a single bond or a linear or branched alkylene group
  • n t1 ' represents an integer of 1 or more and 4 or less
  • m t1 ' represents an integer of 1 to 3
  • P al -Sp al - P al and Sp al the same as P al and Sp al in the above general formula (SAL)
  • the symbol * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • the said alkylene trivalent group means the trivalent group which can remove one hydrogen atom further from an alkylene group.
  • the alkenylene trivalent group is a trivalent group obtained by further removing one hydrogen atom from an alkenylene group, a trivalent group having a free valence in a so-called hydrocarbon chain, such as an alkanetriyl group or an alkyl-ylidene group. Group etc.
  • X t1 is a form (cyclic group) in which X t1 is bonded to Z t1 in the above general formula (T), it is as the above general formula (T ′).
  • n t1 preferably represents an integer of 0 or more and 3 or less, and more preferably, n t1 represents an integer of 0 or more and 2 or less.
  • the general formula (T) is a cyclic group represented by any one of the general formulas (T-1-1) to (T-4-1) and any one of the general formulas (T-5-1) to (T-6-1) It is preferable that it is at least one selected from the group consisting of a chain group represented by
  • the general formula (T-1-1) or the general formula T-2-1) is preferred.
  • the adsorptive group represented by the general formula (T) according to the present invention selects a chain group
  • the general formula (T-5-1) or the general formula (T-5-1) is preferable from the viewpoint of adsorption ability and stability to liquid crystal composition.
  • T-7-1) is preferred.
  • X ta and X tb each independently represent -O-, -S- or CH 2-
  • W t2 represents a single bond or a monovalent to tetravalent organic group
  • W t1 represents a single bond or a linear or branched alkylene group
  • nt1 represents an integer of 0 or more and 4 or less
  • mt1 represents an integer of 1 to 3
  • P al -Sp al - P al and Sp al are the same as P al and Sp al in the above general formula (SAL).
  • SAL general formula
  • * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P al -Sp al - (P al and Sp al is P al and Sp in formula (SAL) is the same as al is represented by), the hydrogen atoms in the molecule of the polymerizable group P al -Sp al -. may be substituted by, * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group) It is preferable that the general formula (T-5-1) represents the general formula (T-5-2).
  • W t1 represents the same meaning as W t1 in the general formula (T-5)
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P al -Sp al - represented by, n t1, n t2 and n t3 is 0 or 1 each independently, a hydrogen atom in the molecule a polymerizable group P al -Sp al - (P al and Sp al is P al in formula (SAL) and Sp is the same as al. may be substituted). ) Specific examples of the above general formula (T-5-1) include the following groups.
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P al -Sp al - (P al and Sp al is P al and Sp in formula (SAL) is the same as al is represented by), the hydrogen atoms in the molecule of the polymerizable group P al -Sp al -.. which may be substituted with * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group)
  • T-6-1 represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P al -Sp al - (P al and Sp al is P al and Sp in formula (SAL) is the same as al is represented by), the hydrogen atoms in the molecule of the polymerizable group P al -Sp al -. may be substituted by, * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group)
  • T-7-1 represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group
  • R c is a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P al -Sp al - (P al and Sp al is P al and Sp in formula (SAL) is the same as al is represented by), the hydrogen atoms in the molecule of the polymerizable group P al -Sp al -. may be substituted by, * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group)
  • * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group
  • a form in which the polar element contained in the adsorptive group or the polar element contained in the polymerizable group is localized is preferable.
  • the adsorptive group is an important structure for vertically aligning the liquid crystal composition, and by the adsorptive group and the polymerizable group being adjacent to each other, better alignment can be obtained, and good to the liquid crystal composition can be obtained. It shows solubility. Specifically, a form having a polymerizable group and an adsorptive group on the same ring of the mesogen group is preferable.
  • one or more polymerizable groups and one or more adsorptive groups are bonded to the same ring, respectively, and at least one of at least one or more adsorptive groups of one or more polymerizable groups, It includes a form in which one is bonded to the other and has a polymerizable group and an adsorptive group on the same ring.
  • the hydrogen atom of the spacer group (Sp a1 ) of the polymerizable group may be substituted by the adsorptive group, and further, the hydrogen atom of the molecule of the adsorptive group is the spacer group (Sp a1 ) of the polymerizable group It also includes the form of bonding.
  • one or more hydrogen atoms of the polymerizable group may be substituted by an adsorptive group.
  • one or more hydrogen atoms of the spacer group Sp al linked to the polymerizable group P al is mentioned embodiment has been replaced with adsorptive group by polymerizable group P al or necessary, more as preferred form, the polymerizable group - include embodiments in which one or more hydrogen atoms in is replaced with adsorptive group represented by the general formula (T) (P a1 -Sp a1 ).
  • R t11a , R t16a and R t151a each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R t151 b and R t 151 c each independently represent an alkyl group having 1 to 3 carbon atoms, or a cyanated alkyl group having 1 to 3 carbon atoms
  • X a and X b represent -O-, -S- or -CH 2-
  • L t151a and L t151 b each independently represent a single bond, a methylene group, an ethylene group, a propylene group, a vinylidene group, a vinylene group, an isopropenylene group or an ethylidene group, n t11 c , n t 151 c , n t 16 c , n t 151 d , n t 151 e , n t 151 f and n t
  • L t151a and L t151a each independently are preferably a methylene group, an ethylene group, a vinylidene group, a vinylene group, an isopropenylene group or an ethylidene group.
  • n t11a , n t11b , n t16a , n t16b , n t151 a and n t151 b is preferably an integer of 1 to 8, and more preferably an integer of 1 to 5.
  • the bending group according to the present invention has a function of inducing the alignment of liquid crystal molecules, and preferably represents a linear or branched alkylene group having 1 to 20 carbon atoms, and a linear carbon atom It is more preferable to represent an alkylene group of the number 1 to 20, and more preferable to represent a linear alkylene group having 2 to 15 carbon atoms.
  • the bending group is preferably bonded to a mesogen group from the viewpoint that the spontaneous alignment compound has a so-called amphiphilic property to the liquid crystal layer.
  • the number of the bending groups is preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3.
  • the spontaneous orientation compound preferably has a bending group for orienting liquid crystal molecules at one end of the mesogenic group, and a structure having a polymerizable group and an adsorptive group at the other end of the mesogenic group .
  • a substance having in one molecule a nonpolar portion having an affinity for the liquid crystal layer and a polar portion having a low affinity for the liquid crystal layer Is considered to lower the interface free energy by being aligned on the interface.
  • the lower limit of the content of the spontaneously aligning compound in the liquid crystal composition of the present invention is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, and more preferably 0.05% by mass.
  • 0.06 mass% is preferable, 0.07 mass% is preferable, 0.08 mass% is preferable, 0.09 mass% is preferable, 0.1 mass% is preferable, 0.12 mass% is preferable, 0.
  • the upper limit of the content of the spontaneously aligning compound in the liquid crystal composition of the present invention is preferably 2.5% by mass, preferably 2.3% by mass, preferably 2.1% by mass, and more preferably 2% by mass.
  • 8 mass% is preferable, 1.6 mass% is preferable, 1.5 mass% is preferable, 1 mass% is preferable, 0.95 mass% is preferable, 0.9 mass% is preferable, and 0.85 mass% is 0.8 mass% is preferable, 0.75 mass% is preferable, 0.7 mass% is preferable, 0.65 mass% is preferable, 0.6 mass% is preferable, 0.55 mass% is preferable, 0.5 mass% is preferable, 0.45 mass% is preferable, and 0.4 mass% is preferable.
  • a particularly preferable specific example of the spontaneous orientation compound according to the present invention is a compound represented by the following general formula (al-1-1).
  • L al5 , L al6 , L al7 and L al8 independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a halogen atom, or P al -S al- (P al and S al have the above general formula .
  • a al3 represents 1,4-cyclohexylene or 1,4-phenylene
  • R ala or R alb are each independently hydrogen atom or the P al -Sp al - represents at least one of R ala or R alb is the P al -Sp al - represents
  • Z al3 represents a single bond, -CH 2 -CH 2- , -CH 2 -O- or O-CH 2-
  • R al 4 represents an adsorptive group represented by the above general formula (T), p al3 and p al4 each independently represent 0 or 1.
  • one of L AL7 and L AL8 is, preferably represents an alkyl group having 1-5 carbon atoms.
  • R ala and R alb above P al -Sp al - preferably represents a.
  • R al 4 is a group represented by any one of the above general formulas (T-1-1) to (T-4-1) or the formula (T-1-1.1), (T-6) -1.1) or (T-5-1.1) is preferred.
  • Preferred compounds include compounds represented by the following formulas (AL-1.1) to (AL-3.6).
  • the lower limit of the preferable content of the total of the compound represented by the general formula (i) and the spontaneously orienting compound is 0.1%, 0.2%, 0.25%, 0.3 %, 0.35%, 0.4%, 0.45%, 0.5%, 0.55% and 0.6%.
  • the upper limit of the preferable total is 3.0%, 3.8%, 3.5%, 3.2%, 3.0%, 2.8%, and 2. 5%, 2.2%, 2.0%, 1.8%, 1.5%, 1.2%, 1.0%, 0.8% %, 0.6% and 0.5%.
  • the liquid crystal composition according to the present invention contains the polymerizable compound (polymerizable monomer) represented by the general formula (i) and the spontaneously orienting compound, but other polymerizable compounds may be used in combination.
  • R p1 represents a hydrogen atom, a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted by a halogen atom, a hydrogen atom is An alkoxy group having 1 to 15 carbon atoms which may be substituted by a halogen atom, an alkenyl group having 2 to 15 carbon atoms which may optionally be substituted by a halogen atom, a hydrogen atom is substituted by a halogen atom And optionally represents an alkenyloxy group having 2 to 15 carbon atoms or -Sp p2 -P p2 ; P p1 and P p2 are each independently represented by general formula (P p1 -1) to formula (P p1 -9)
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms
  • W p11 is a single bond, —O -, -COO-, or a methylene group
  • t p11 represents 0, 1 or 2, but when there are a plurality of R p11 , R p12 , W p11 and / or t p11 in the molecule, they are respectively identical Or may be different.
  • Represents one of the Sp p1 and Sp p2 are each independently a single bond or an alkylene group having 1 to 30 carbon atoms (-CH 2- in the alkylene group is -O- or -CO- as long as the oxygen atoms are not directly linked to each other).
  • a p2 is a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2, 5-diyl group, naphthalene-2,6-diyl group, indane-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5 -Represents a diyl group, wherein A p2 is unsubstituted or an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an
  • ⁇ when ⁇ is Sp p1 , or when m p1 is 2 or 3, ⁇ connects to S p p1 or Z p1 , ⁇ ⁇ bonds to Z p1, and one or more hydrogen atoms in the structure are
  • a p3 is the formula (A p3 -11) to (A p3 -19)
  • ⁇ binds to Z p2
  • ⁇ ⁇ binds to R p1
  • m p3 binds to R p1
  • one or more hydrogen atoms in the structure Is 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 Or a group which may be substituted by a nitro group
  • m p2 and m p3 each independently represent 0, 1, 2, or 3
  • m p1 and m p4 each independently represent 1, 2 or 3, but P p1 , Sp p1 , A When a plurality of p 1 , Z p 1 , Z p 2 , A p 3 and R p 1 respectively
  • R p1 is preferably -Sp 2 -P p 2 .
  • P p1 and P p2 be each independently any one of the formulas (P p1 -1) to (P p1 -3), and it is preferable that it is (P p1 -1).
  • R p11 and R p12 are preferably each independently a hydrogen atom or a methyl group.
  • m p1 + m p4 is preferably 2 or more, preferably 2 or 3.
  • the chain is preferably an alkylene group having 1 to 10 carbon atoms or a single bond.
  • a p2 is preferably 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl or naphthalene-2,6-diyl; 4-phenylene group, 1,4-cyclohexylene group, phenanthrene-2,7-diyl group or naphthalene-2,6-diyl group is preferable, and when m p2 + m p3 is 0, phenanthrene 2,7-diyl group is Preferably, when m p 2 + m p 3 is 1, 2 or 3, a 1,4-phenylene group or a 1,4-cyclohexylene group is preferable.
  • One or more hydrogen atoms in the structure of A p2 may be substituted with a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom in order to improve the compatibility with the liquid crystal compound.
  • a p1 is preferably of the formula (A p1 -15), (A p1 -16), (A p1 -17) or (A p1 -18).
  • One or more hydrogen atoms in the structure of A p1 may be substituted by a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom in order to improve the compatibility with the liquid crystal compound.
  • One or more hydrogen atoms in the structure of A p3 may be substituted with a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom in order to improve the compatibility with the liquid crystal compound.
  • n p2 + m p3 is preferably 0, 1, 2 or 3 and 1 or 2 is preferable.
  • the total content of the compound represented by the general formula (P) is preferably 0.05 to 10% of the composition containing the compound represented by the general formula (P) of the present application, It is preferable to contain 0.1 to 8%, to contain 0.1 to 5%, to contain 0.1 to 3%, and to contain 0.2 to 2%. Preferably, 0.2 to 1.3% is contained, 0.2 to 1% is preferably contained, and 0.2 to 0.56% is preferably contained.
  • the preferable lower limit of the total content of the compounds represented by General Formula (P) is 0.01% with respect to the composition containing the compound represented by General Formula (P) of the present application, and 0. 0%. 03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% %.
  • the preferred upper limit of the total content of the compounds represented by general formula (P) is 10% and 8% with respect to the composition containing the compound represented by general formula (P) of the present application 5%, 3%, 1.5%, 1.2%, 1%, 0.8% and 0.5%.
  • the content is small, the effect of adding the compound represented by the general formula (P) is difficult to appear, and problems such as weak alignment control of the liquid crystal composition or weakening with time occur. There are problems such as a large amount remaining later, long time for curing, and a decrease in the reliability of the liquid crystal. Therefore, the content is set in consideration of these balances.
  • the compounds represented by General Formula (P) are preferably compounds represented by General Formula (P-1), General Formula (P-2), General Formula (P-3) and General Formula (P-4) .
  • P p11 , P p12 , P p21 , P p22 , P p31 , P p32 , P p41 and P p42 each independently represent the same meaning as P p1 in the general formula (P)
  • Sp p41 and Sp p42 each independently represent the same meaning as Sp p1 in formula (P)
  • Ap11 , Ap12 , Ap13 , Ap21 , Ap22 , Ap23 , Ap32 and Ap42 are each independently a 1,4-phenylene group, a 1,4-cyclohexylene group, anthracene-2,6- Diyl group, phenanthrene-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group,
  • a p41 represents the same meaning as A p1 of the general formula (P)
  • a p43 has the same meaning as A p3 in formula (P)
  • P p11 , P p12 , P p21 , P p22 , P p31 , P p32 , P p41 and P p42 are each independently a group (P p1 -1) to a group (P p1 in the same manner as P p1 in formula (P)) It is preferably any one of P p1 -3), preferably (P p1-1 ), and R p11 and R p12 are preferably each independently a hydrogen atom or a methyl group.
  • the hydrogen atom in the group may be substituted with a halogen atom, but a linear alkylene group having 1 to 10 carbon atoms or a single bond is preferable.
  • Ap11 , Ap12 , Ap13 , Ap21 , Ap22 , Ap23 , Ap32 and Ap42 are each independently a 1,4-phenylene group, a 1,4-cyclohexylene group, anthracene-2,6- Diyl group, phenanthrene-2,7-diyl group or naphthalene-2,6-diyl group is preferable, 1,4-phenylene group, 1,4-cyclohexylene group, phenanthrene-2,7-diyl group or naphthalene-2 , 6-diyl group is preferred.
  • a 1,4-phenylene group or a 1,4-cyclohexylene group is independently preferred, and the structure thereof is to improve the compatibility with the liquid crystal compound.
  • one or more hydrogen atoms may be substituted by a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom.
  • a phenanthrene-2,7-diyl group is preferable, and in order to improve the compatibility with the liquid crystal compound, one or two or more hydrogen atoms in the structure thereof are a methyl group, an ethyl group, It may be substituted by a methoxy group, an ethoxy group or a fluorine atom.
  • Z p21 , Z p22 , Z p41 and Z p42 present in the molecule is- (CH 2 ) 2 -COO-,-(CH 2 ) 2 -OCO-, -O-CO- ( CH 2) 2 -, - COO- (CH 2) 2 - is a linking group selected from the group consisting of, it is preferred the other is a single bond.
  • Preferred examples of the compound represented by General Formula (P-1) according to the present invention include polymerizable compounds represented by the following Formula (P-1-1) to Formula (P-1-46).
  • P p11 , P p12 , Sp p11 and Sp p12 have the same meaning as P p11 , P p12 , Sp p11 and Sp p12 in general formula (P-1)
  • Preferred examples of the compound represented by General Formula (P-2) according to the present invention include polymerizable compounds represented by the following Formula (P-2-1) to Formula (P-2-12).
  • P p21 , P p22 , Sp p21 and Sp p22 have the same meaning as P p21 , P p22 , Sp p21 and Sp p22 in formula (P-2)
  • P-3 polymerizable compounds represented by the following formulas (P-3-1) to (P-3-15) can be mentioned.
  • P p31 , P p32 , Sp p31 and Sp p32 have the same meaning as P p31 , P p32 , Sp p31 and Sp p32 in general formula (P-3).
  • Preferred examples of the compound represented by the general formula (P-4) according to the present invention include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-19).
  • the liquid crystal composition of the present invention may contain ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, ultraviolet absorbers, light stabilizers, infrared absorbers and the like in addition to the above-mentioned compounds.
  • antioxidant examples include hindered phenols represented by general formula (H-1) to general formula (H-4).
  • R H1 is 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 It represents an alkenyloxy group having 2 to 10 carbon atoms, one -CH 2 present in the radical - or non-adjacent two or more -CH 2 - are each independently -O- or -S- And one or more hydrogen atoms present in the group may be independently substituted with a fluorine atom or a chlorine atom.
  • it is an alkyl group having 2 to 7 carbon atoms, an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms. More preferably, it is an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.
  • the hydrogen atoms in the 1,4-phenylene group may be each independently substituted with a fluorine atom or a chlorine atom.
  • one or more non-adjacent two or more -CH 2 -in the 1,4-cyclohexylene group is substituted by -O- or -S- It may be done.
  • the hydrogen atoms in the 1,4-cyclohexylene group may be each independently substituted with a fluorine atom or a chlorine atom.
  • antioxidants include, for example, formulas (H-11) to (H-15).
  • the content of the antioxidant is preferably 10 mass ppm or more, preferably 20 mass ppm or more, and more preferably 50 mass ppm or more.
  • the upper limit in the case of containing an antioxidant is 10000 mass ppm, 1000 mass ppm is preferable, 500 mass ppm is preferable, and 100 mass ppm is preferable.
  • the liquid crystal composition of the present invention has a dielectric anisotropy ( ⁇ ) at ⁇ 20 ° C. of ⁇ 2.0 to ⁇ 8.0, preferably ⁇ 2.0 to ⁇ 6.0, and ⁇ 2.0 to -5.0 is more preferable, and -2.5 to -5.0 is particularly preferable.
  • the liquid crystal composition of the present invention has a refractive index anisotropy ( ⁇ n) at 20 ° C. of 0.08 to 0.14, preferably 0.09 to 0.13, and more preferably 0.09 to 0.12. Particularly preferred. More specifically, in the case of a thin cell gap, it is preferably 0.10 to 0.13, and in the case of a thick cell gap, it is preferably 0.08 to 0.10.
  • the liquid crystal composition of the present invention has a viscosity ( ⁇ ) of 10 to 50 mPa ⁇ s at 20 ° C., preferably 10 to 45 mPa ⁇ s, preferably 10 to 40 mPa ⁇ s, and 10 to 35 mPa ⁇ s.
  • S is preferable, 10 to 30 mPa ⁇ s is preferable, 10 to 25 mPa ⁇ s is more preferable, and 10 to 22 mPa ⁇ s is particularly preferable.
  • the liquid crystal composition of the present invention has a rotational viscosity ( ⁇ 1 ) at 50 ° C. of 50 to 160 mPa ⁇ s, preferably 55 to 160 mPa ⁇ s, more preferably 60 to 160 mPa ⁇ s, 60 Of from 150 to 150 mPa ⁇ s, preferably from 60 to 140 mPa ⁇ s, preferably from 60 to 130 mPa ⁇ s, preferably from 60 to 125 mPa ⁇ s, preferably from 60 to 120 mPa ⁇ s.
  • the viscosity is more preferably 60 to 115 mPa ⁇ s, more preferably 60 to 110 mPa ⁇ s, and particularly preferably 60 to 100 mPa ⁇ s.
  • the liquid crystal composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T ni ) of 60 ° C. to 120 ° C., preferably 70 ° C. to 100 ° C., particularly preferably 70 ° C. to 85 ° C.
  • T ni nematic phase-isotropic liquid phase transition temperature
  • a spontaneous alignment compound for example, in the case where the entire liquid crystal composition according to the present invention exhibits negative dielectric anisotropy, a spontaneous alignment compound, a polymerizable compound (polymerizable monomer) represented by general formula (i), and a general formula Containing one or more compounds selected from the group of compounds represented by N-1), (N-2) and (N-3), and a compound represented by the general formula (L) Is preferred.
  • the upper limit value of the ratio of the component constituted only of the compound selected from the compound group represented by N-3) and the compound represented by the general formula (L) is 100% by mass, 99% by mass, 98% %, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, It is preferable that it is 85 mass% and 84 mass%.
  • a spontaneous orientation compound a polymerizable compound represented by the general formula (i), a general formula (N-1), a general formula (N-2), a general formula
  • the lower limit value of the proportion of the component constituted only of the compound selected from the compound group represented by the formula (N-3) and the compound represented by the general formula (L) is 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 It is preferable that they are mass%, 96 mass%, 97 mass%, 98 mass%, and 99 mass%.
  • a spontaneous orientation compound a polymerizable compound represented by the general formula (i), a general formula (N-1a), a general formula (N-1b), and a general formula
  • the lower limit value is 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% by mass, 94% by mass, 95% by mass, 96% by mass, 97% by mass, 98% by mass, and 99% by mass.
  • a spontaneous orientation compound a polymerizable compound represented by the general formula (i), a compound represented by the general formula (P), and a compound represented by the general formula (N-1a)
  • the lower limit value of the proportion of the component constituted only with is 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass% 90% by weight, 91% by weight, 92% by weight, 93% by weight, 94% by weight, 95% by weight, 96% by weight, 97% by weight, 98% by weight.
  • liquid crystal composition in the case where importance is placed on orientation, a spontaneous orientation compound, a polymerizable compound represented by the general formula (i), and a compound represented by the general formula (P) And a compound represented by General Formula (N-1-1), General Formula (N-1-2), General Formula (N-1-3) or General Formula (N-1-4) preferable.
  • the spontaneously orienting compound, the polymerizable compound represented by the general formula (i), and the compound represented by the general formula (P) It is preferable to include the general formula (N-1-10) or the general formula (N-1-11).
  • liquid crystal composition when importance is attached to the response speed, one or two or more types of spontaneous orientation compounds and a polymerization represented by two or more types of general formula (II-1) described later It is preferable that the compound essentially contains a sex compound, and that it contains the general formula (N-1-10) or the general formula (N-1-11).
  • the upper limit value of the proportion of the component constituted only of the compound represented by the general formula (L) is 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93 It is preferable that they are mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%.
  • the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-) The lower limit value of the proportion of the component constituted only of the compound represented by 1e) and the compound represented by the general formula (L) is 78% by mass, 80% by mass, 81% by mass, 83% by mass, 85% by 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%, It is preferable that it is 98 mass%.
  • the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-1e) Compounds represented by the general formula (L-1), general formula (L-3), general formula (L-4), general formula (L-5) and general formula (L-6) 99% by weight, 98% by weight, 97% by weight, 96% by weight, 95% by weight, 94% by weight, 93% by weight, 92% by weight, 91% by weight It is preferable that they are 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%, 83 mass%, 82 mass%, 81 mass%, 80 mass%.
  • the lower limit value of the ratio of the component constituted only of the compound is 68 mass%, 70 mass%, 71 mass%, 73 mass%, 75 mass%, 78 mass%, 80 mass%, 81 mass%, 83 mass %, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, It is preferable that it is 97 mass% and 98 mass%.
  • the liquid crystal display device using the liquid crystal composition of the present invention has the remarkable feature of high-speed response, and additionally, the tilt angle is sufficiently obtained, and there is no problem with unreacted polymerizable compounds.
  • VHR voltage holding ratio
  • problems such as alignment failure and display failure are sufficiently suppressed.
  • the tilt angle and the residual amount of the polymerizable compound can be easily controlled, it is easy to optimize and reduce the energy cost for manufacturing, which is optimal for improvement of production efficiency and stable mass production.
  • the liquid crystal display element using the liquid crystal composition of the present invention is particularly useful for a liquid crystal display element for driving an active matrix, and a liquid crystal display element for PSA mode, PSVA mode, VA mode, PS-IPS mode or PS-FFS mode It can be used for
  • a liquid crystal display device comprises a first substrate and a second substrate disposed opposite to each other, a common electrode provided on the first substrate or the second substrate, and the first substrate or the first substrate. It is preferable to have a pixel electrode provided on a second substrate and having a thin film transistor, and a liquid crystal layer containing a liquid crystal composition provided between the first substrate and the second substrate. If necessary, an alignment film for controlling the alignment direction of liquid crystal molecules may be provided on the opposite surface side of at least one of the first and second substrates so as to be in contact with the liquid crystal layer. As the alignment film, a vertical alignment film, a horizontal alignment film, etc.
  • a rubbing alignment film for example, polyimide alignment film
  • a photo alignment film decomposition type polyimide alignment
  • Well-known alignment films, such as film etc. can be used.
  • a color filter may be appropriately provided on the first substrate or the second substrate, and a color filter may be provided on the pixel electrode or the common electrode.
  • the two substrates of the liquid crystal cell used in the liquid crystal display device according to the present invention may be a flexible transparent material such as glass or plastic, and one of them may be an opaque material such as silicon.
  • a transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be produced, for example, by a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method or the like.
  • a method of producing a color filter by the pigment dispersion method will be described by way of example.
  • a curable coloring composition for a color filter is applied on the transparent substrate, subjected to a patterning treatment, and cured by heating or light irradiation. By performing this process for each of three colors of red, green, and blue, it is possible to create a pixel portion for a color filter.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided.
  • first substrate and the second substrate be opposed so that the common electrode and the pixel electrode layer are inside.
  • the distance between the first substrate and the second substrate may be adjusted via a spacer.
  • the polarizing axis of each polarizing plate can be adjusted to adjust the viewing angle and contrast to be good.
  • retardation films for widening the viewing angle can also be used.
  • the spacer include glass particles, plastic particles, alumina particles, and photoresist materials.
  • a sealing agent such as an epoxy-based thermosetting composition is screen-printed on the substrate in a form provided with a liquid crystal injection port, the substrates are bonded to each other, and heating is performed to thermally cure the sealing agent.
  • a second aspect of the present invention is a liquid crystal composition used for a liquid crystal display device having no alignment film on the surface of at least one of a pair of substrates, comprising a polymerizable compound having two or more biphenyl skeletons. It is a liquid crystal composition.
  • a difference occurs in the reaction rate, so that unevenness in alignment, display failure, and the like can be reduced.
  • the polymerizable compound having a biphenyl skeleton is a concept including a terphenyl as long as it has a biphenyl skeleton in which two benzene rings are directly linked. Therefore, a polymerizable compound having two or more biphenyl skeletons means that two or more kinds of polymerizable compounds having a biphenyl skeleton in which two benzene rings are directly linked to each other exist.
  • Examples of the polymerizable compound having a biphenyl skeleton according to the present invention include a polymerizable compound having a biphenyl skeleton among polymerizable compounds represented by the formula (i). Further, the polymerizable compound having a biphenyl skeleton according to the present invention has the following formula (II-1):
  • R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 210 , R 211 , R 212 , R 213 and R 214 are each independently, P 21 -S 21 -, from a good carbon atoms 1 be substituted by a fluorine atom 18 alkyl group, an alkoxy group are replaced by fluorine atoms from a good carbon number of 18
  • P 21 represents any of (R-I) to (R-IX) in the above general formula (i)
  • S 21 represents a single bond or a single bond or a hydrogen atom (a fluorine atom) or a hydrogen atom.
  • n 21 represents 0, 1 or 2.
  • P 21 -S 21- in one molecule of the compound represented by the general formula (II-1), and four or less P 21 -S 21 - preferably has a, P 21 -S 21 existing in one molecule of the formula (II-1) - number of, preferably 1 to 4, more preferably 1 to 3,
  • the number of P 21 -S 21- in the molecule of the compound represented by the general formula (II-1) is particularly preferably 2 or 3.
  • the compound represented by the general formula (II-1) has two benzene rings (biphenyl skeletons) and has at least one P 21 -S 21- in these two benzene rings.
  • the compound represented by the general formula (II-1) exerts an action and an effect as a polymerizable compound.
  • R 201 and R 210 each independently, P 21 -S 21 - is preferably, in this case, R 201 and R 210 identical P 21 -S 21 - even, different P 21 -S 21 - may be.
  • R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 , R 211 , R 212 , R 213 and R 214 are each independently, P 21 -S 21 -, alkoxy group of the alkyl group are substituted by fluorine atoms from a good carbon atoms 1 also 18, from a good carbon atoms 1 be substituted by a fluorine atom 18,
  • a fluorine atom or a hydrogen atom is represented, but in this case, the preferred carbon atom number of the alkyl group and the alkoxy group is 1 to 16, more preferably 1 to 10, and still more preferably 1 to 8. It is more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 to 3.
  • the alkyl group and the alkoxy group may be linear or branched, and linear is particularly preferable.
  • R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 , R 211 , R 212 , R 213 and R 214 are each independently, P 21 -S 21 -, alkyl group of one to three carbon atoms, alkoxy group having one to three carbon atoms, is preferably a fluorine atom or a hydrogen atom, P 21 -S 21 -, A fluorine atom or a hydrogen atom is more preferable, and a fluorine atom or a hydrogen atom is more preferable.
  • P 21 is preferably a formula (RI), more preferably an acryl group or a methacryl group, and still more preferably a methacryl group.
  • S 21 is preferably a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond.
  • n 21 is preferably 0.
  • the liquid crystal composition according to the present invention preferably contains 2 to 6 types, and more preferably 2 to 5 types of polymerizable compounds having a biphenyl skeleton represented by the above general formula (II-1). It is further preferable to include 2 to 4 types, further preferably 2 to 3 types, and particularly preferably 2 types. If two or more kinds of polymerizable compounds having a biphenyl skeleton represented by the above general formula (II-1) having different chemical structures are included, a difference occurs in the reaction rate, so that unevenness in alignment, display defects and the like can be reduced. it can.
  • a polymerizable compound represented by the above formula (P) specifically, from the above general formula (P-1-1), a compound represented by the general formula (P-1) -46), general formula (P-2-1) to general formula (P-2-12), general formula (P-3-1) to general formula (P-3-15), and general formula (P- Compounds represented by general formula (P-4-19) from the compound 4-1) may be used.
  • Sp xx is an alkylene group having 1 to 8 carbon atoms, or -O- (CH 2 ) s- (wherein, s is an integer of 1 to 7) And the oxygen atom is bonded to the ring), and the hydrogen atom in the 1,4-phenylene group is further selected from -F, -Cl, -CF 3 , -CH 3 or the following formula (R- 1) to formula (R-9)
  • each of R 11 , R 12 , R 13 , R 14 and R 15 independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m r5 , m and each of r7 , n r5 and r7 independently represents 0, 1 or 2.
  • S 11 , S 12 and S 13 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH 2 — or two or more not adjacent to each other in the alkylene group And -CH 2- may be substituted with -O-, -OCO- or -COO- so that the oxygen atom is not directly adjacent.
  • P 13 and S 13 may be the same or different. It may be replaced by any of.
  • R M1 , R M2 and R M3 are each independently an alkyl group having 1 to 5 carbon atoms, a fluorine atom or hydrogen
  • the polymerizable compound etc. which are represented by any of the atom are represented.
  • the total content of the polymerizable compounds having two or more kinds of biphenyl skeletons in the liquid crystal composition may be 0.02 to 10% by mass, and the lower limit of the content is preferably 0.02% by mass, 0 .03 mass% is preferable, 0.04 mass% is preferable, 0.05 mass% is preferable, 0.06 mass% is preferable, 0.07 mass% is preferable, 0.08 mass% is preferable, 0.09 mass% is preferable 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, 0.3% by mass is preferable, and 0.35% by mass 0.4 mass% is preferable, 0.5 mass% is preferable, 0.55 mass% is preferable, and 5 mass%, 4.5 mass% is preferable, and 4 mass% is preferable as the upper limit of the content.
  • 3.5 mass% is preferable, 3 quality % Is preferable, 2.5 mass% is preferable, 2 mass% is preferable, 1.5 mass% is preferable, 1 mass% is preferable, 0.95 mass% is preferable, 0.9 mass% is preferable, and 0. 85% by mass is preferable, 0.8% by mass is preferable, 0.75% by mass is preferable, 0.7% by mass is preferable, 0.65% by mass is preferable, 0.6% by mass is preferable, and 0.55% by mass % Is preferred.
  • the liquid crystal composition according to the present invention preferably includes a spontaneous orientation monomer having a polar group and a chemical structure different from each of the polymerizable compounds having two or more types of biphenyl skeletons.
  • spontaneous orientation monomer the above-mentioned spontaneous orientation compound can be suitably used.
  • liquid crystal composition according to the present invention, two or more kinds of the polymerizable compound having a biphenyl skeleton represented by the above general formula (II-1) and one kind of the above-mentioned spontaneous orientation monomer
  • One or two or more compounds selected from a group of compounds represented by general formulas (N-1a) to (N-1 g), and a compound represented by general formula (L) It is preferable that these compounds contain a species or two or more species, and that these compounds account for 85 to 100% by mass of the liquid crystal composition.
  • a first substrate and a second substrate disposed opposite to each other, a liquid crystal layer filled between the first substrate and the second substrate, and the first substrate.
  • a plurality of gate bus lines and data bus lines arranged in a matrix, thin film transistors provided at intersections of the gate bus lines and the data bus lines, and pixel electrodes driven by the thin film transistors are provided for each pixel.
  • a polymerizable compound having two or more biphenyl skeletons between an electrode layer, a common electrode formed on the first substrate or the second substrate, and the first substrate and the second substrate It is a liquid crystal display element which is not equipped with an alignment film on the surface of at least one substrate which has a cured resin component.
  • polymerizable compound having a biphenyl skeleton for example, a polymerizable compound represented by the formula (i), a polymerizable compound represented by the formula (II-1) as in the second liquid crystal display element described above A polymerizable compound represented by the above formula (P), a polymerizable compound represented by the above formula (XX-1) to the general formula (XX-13), and a formula (RM-14) from the above formula (RM-1) And the polymerizable compounds represented by the above formulas (I-1-1) to (I-7-6), and two or more selected from these polymerizable compounds can be mentioned. It can be used.
  • the polymerizable compound having two or more kinds of biphenyl skeletons is represented by one or two or more kinds of polymerizable compounds represented by the above-mentioned formula (i) and one or more kinds of the above-mentioned formula (P) It is preferable that it is a polymerizable compound.
  • an appropriate polymerization rate is desirable.
  • the method of polymerizing by irradiating active energy rays singly or in combination or sequentially is preferable.
  • a polarized light source may be used or a non-polarized light source may be used.
  • polymerization is carried out in a state where the liquid crystal composition is held between two substrates, at least the substrate on the irradiation surface side must be given appropriate transparency to active energy rays.
  • the alignment state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field or temperature, and irradiation of active energy rays is further performed. It is also possible to use a means of polymerization.
  • the alternating electric field to be applied is preferably an alternating current having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage.
  • the pretilt angle of the liquid crystal display element of the PSVA 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 at the time of irradiation of active energy rays such as ultraviolet rays or electron beams used when polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited.
  • active energy rays such as ultraviolet rays or electron beams
  • the liquid crystal composition of the present invention when applied to a liquid crystal display element provided with a substrate having no alignment film, it is applied to a liquid crystal display element provided with a substrate having the above alignment film.
  • the temperature range may be wider than the temperature range.
  • a metal halide lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, or the like can be used as a lamp that generates ultraviolet light.
  • a wavelength of the ultraviolet-ray to irradiate it is preferable to irradiate the ultraviolet-ray of the wavelength range which is not an absorption wavelength range of a liquid crystal composition, and it is preferable to cut and use an ultraviolet-ray as needed.
  • the intensity of the ultraviolet light to be irradiated is preferably 0.1 mW / cm 2 to 100 W / cm 2, and more preferably 2 mW / cm 2 to 50 W / cm 2 .
  • the energy amount of the ultraviolet rays to be irradiated can be adjusted as appropriate, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2 .
  • the intensity may be changed.
  • the irradiation time of the ultraviolet light is appropriately selected depending on the intensity of the ultraviolet light to be irradiated, preferably 10 seconds to 3600 seconds, and more preferably 10 seconds to 600 seconds.
  • Example 1 In a reaction vessel equipped with a stirrer, a condenser, and a thermometer, 19 g of 5-bromobenzene 1,3-diol, 2.5 g of pyridinium p-toluenesulfonate, and 200 ml of dichloromethane are charged, and 3,4-dihydro-2H-pyran 12 g was dropped. Furthermore, it was made to react at room temperature for 4 hours. After completion of the reaction, the organic layer was washed with water and saturated brine, and the solvent was evaporated to obtain 33 g of a compound represented by the formula (1).
  • reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with a 5% aqueous hydrochloric acid solution, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a silica gel column to obtain 26 g of the objective compound represented by the formula (i-33).
  • Example 2 In a reaction vessel equipped with a stirrer, condenser and thermometer, 33 g of the compound represented by the formula (1) synthesized in Example 1, 15 g of acrylic acid tertiary butyl ester, 14 g of triethylamine, 800 mg of palladium acetate, 200 ml of dimethylformamide The reactor was heated to 100 ° C.
  • the concentrate 17 g of methacrylic acid, 230 mg of dimethylaminopyridine, and 150 ml of dichloromethane are charged in a reaction vessel equipped with a stirrer, condenser and thermometer, and the reaction vessel is maintained at 5 ° C. or less with an ice bath. Under an atmosphere, 24 g of diisopropyl carbodiimide was slowly dropped. After completion of the dropwise addition, the reaction vessel was returned to room temperature and allowed to react for 5 hours. The reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with pure water and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out using a silica gel column to obtain 24 g of a compound represented by the formula (5).
  • reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with a 5% aqueous hydrochloric acid solution, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a silica gel column to obtain 24 g of the objective compound represented by the formula (i-34).
  • Example 3 In an autoclave equipped with a stirrer, 32 g of the compound represented by the formula (4) synthesized in Example 1 and 200 ml of THF are charged, 20 ml of an ethanol solution and 1.6 g of 5% palladium carbon (hydrous) are charged and contacted with hydrogen gas Hydrogen reduction was performed.
  • reaction solution was filtered and then the solvent was distilled off. Further, 32 g of the concentrate and 200 ml of THF were charged into a reaction vessel equipped with a stirrer and a thermometer, and a mixed solution of 10 ml of methanol solution and 1 ml of hydrochloric acid was slowly dropped. After the completion of dropping, the mixture was further allowed to be for 2 hours.
  • reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with pure water and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out by column chromatography using a double volume (weight ratio) of silica gel to obtain 23 g of the objective compound represented by the formula (8).
  • reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with a 5% aqueous hydrochloric acid solution, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out using a silica gel column to obtain 22 g of the objective compound represented by the formula (i-35).
  • reaction solution was filtered, then 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with a 5% aqueous hydrochloric acid solution, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a silica gel column to obtain 24 g of the objective compound represented by the formula (i-2).
  • the liquid crystal composition was filtered with a membrane filter (PTFE 13 m-0.2 ⁇ m, manufactured by Agilent Technologies), and allowed to stand for 15 minutes under vacuum reduced pressure conditions to remove dissolved air. This was washed with acetone and weighed 0.5 g in a fully dried vial, and allowed to stand in an environment of ⁇ 25 ° C. for 10 days. Then, the presence or absence of precipitation was observed visually and it determined in the following two steps.
  • PTFE 13 m-0.2 ⁇ m manufactured by Agilent Technologies
  • illuminance measured at the center wavelength of 365nm condition was adjusted to 100 mW / cm 2, was irradiated with ultraviolet light at an accumulated light intensity of 10J / cm 2.
  • the above ultraviolet irradiation condition is referred to as irradiation condition 1.
  • irradiation condition 1 Under the irradiation condition 1, a pretilt angle is given to liquid crystal molecules in the liquid crystal cell.
  • the illuminance was measured at a center wavelength of 313nm is adjusted to 3 mW / cm 2, further irradiated with ultraviolet light at an accumulated light intensity 20 J / cm 2, to obtain a liquid crystal display device .
  • the aforementioned ultraviolet irradiation conditions are referred to as irradiation conditions 2. Under the irradiation condition 2, the residual amount of the polymerizable compound in the unreacted liquid crystal cell under the irradiation condition 1 is reduced.
  • pretilt angle of the liquid crystal display element was measured and used as a pretilt angle (initial).
  • the backlight was illuminated for 10 hours while applying a voltage of 100 Hz at a frequency of 100 Hz to the liquid crystal display element at a rectangular wave of 30 V.
  • the pretilt angle was measured and used as the pretilt angle (after the test).
  • the pretilt angle was measured using Syntech OPTIPRO.
  • the magnitude of the voltage of 30 V is several times larger than the normal drive voltage, which is an acceleration test.
  • the nematic phase-isotropic liquid phase transition temperature (T ni ) of LC-1 is 75 ° C.
  • the solid phase-nematic phase transition temperature (T CN ) is -33 ° C.
  • the refractive index anisotropy ( ⁇ n) is 0.11.
  • the dielectric anisotropy ( ⁇ ) was ⁇ 2.8
  • the rotational viscosity ( ⁇ 1 ) was 98 mPa ⁇ s.
  • the refractive index anisotropy ( ⁇ n), the dielectric anisotropy ( ⁇ ), and the rotational viscosity ( ⁇ 1) are all measurement results at 25 ° C. (the same applies hereinafter).
  • Comparative Examples 1 to 4 Based on 100 parts by mass of LC-1, 1.0 part by mass of the following spontaneously orienting compound (AL-2.2) and 0.3 parts by mass of a compound represented by the formula (RM-R1) A liquid crystal composition containing the resulting polymerizable compound is referred to as Comparative Example 1.
  • Comparative Example 2 To 100 parts by mass of the liquid crystal composition LC-1, 1.0 part by mass of the spontaneously orienting monomer (AL-2, 2) and 0.3 parts by mass of the compound represented by the formula (RM-R2) A liquid crystal composition containing the resulting polymerizable compound is referred to as Comparative Example 2.
  • Examples 1 to 3 A liquid crystal composition was prepared in the same manner as in Comparative Example 1 by adding the spontaneously orienting monomer (AL-2.2) and the following polymerizable compound (i-33) to LC-1 in the amounts shown in Table 5 below, respectively. did.
  • Table 5 shows the results of low temperature storage stability of Examples 1 to 3, the vertical alignment test of the polymerizable compound after ultraviolet irradiation, and the tilt stability test.
  • FIG. 1 is a photograph of a cell injected with the liquid crystal composition of Comparative Example 2 and FIG. The white-appearing part in the cell peripheral part of FIG.
  • FIG. 1 is not vertically oriented, but is a part which is obliquely or horizontally oriented, and shows uneven alignment. Many white spots are seen in FIG. 1, and many regions which are not vertically oriented are present. In addition, a domain divided into four is seen in the cell. This is a dripping nonuniformity, and when the liquid crystal composition is dripped and spreads when the compositions intersect, it is a nonuniformity which can not be uniformly mixed, and this is also a kind of defect. However, in FIG. 2, almost no white line is seen, and black is uniformly shown. In FIG. 1 and FIG. 2, the white straight line which is partially visible is not an uneven alignment but a scratch on a physical glass, so it is not an uneven alignment.
  • the change in pretilt with time in the present invention is considered to be affected by the hardness of the polymer film, and the harder polymer film is obtained by increasing the amount of the polymerizable compound represented by formula (i). It is considered that the pretilt is formed, and the amount of change with time of the pretilt is small.
  • the substrate with a polyimide alignment film that induces vertical alignment when confirming the pretilt angle change amount in order to evaluate the polymer stability of each monomer in a state where the initial pretilt angle is constant, the substrate with a polyimide alignment film that induces vertical alignment when confirming the pretilt angle change amount.
  • a liquid crystal composition is formed on a first substrate by additionally forming a first substrate (common electrode substrate) not having an alignment film and a second substrate (pixel electrode substrate) not having an alignment film. It was confirmed that similar results were obtained also in the case of using a cell gap 3.2 ⁇ m liquid crystal cell which was dropped and held on a second substrate and the sealing material was cured.
  • Example 4 to 58 The addition of the polymerizable compounds (i-1) to (i-19) shown below and the spontaneous orientation compounds (AL-1.4) to (AL-2.33) shown in Tables 6, 8 and 10 below, respectively A liquid crystal composition was prepared in the same manner as in Comparative Example 1 except that the amount was added to LC-1.
  • the results of low temperature storage stability of Examples 4 to 58, vertical alignment test of the polymerizable compound after ultraviolet irradiation, and tilt stability test are shown in Tables 7, 9 and 11.
  • Example 59 to 73 0.8 parts by mass of the spontaneously orienting compound (AL-2.5), 0.3 parts by mass of the compound represented by the formula (RM-R1), and 100 parts by mass of the liquid crystal composition LC-1
  • a liquid crystal composition containing a polymerizable compound obtained by adding 0.1 parts by mass of a compound represented by the formula (i-1) is set as an example 59.
  • a liquid crystal composition containing a polymerizable compound obtained by adding 0.1 parts by mass of a compound represented by the formula (i-2) is referred to as example 60.
  • a liquid crystal composition containing a polymerizable compound obtained by adding 0.1 parts by mass of a compound represented by the formula (i-6) is set as an example 61.
  • Example 62 A liquid crystal composition containing a polymerizable compound to which 0.1 parts by mass of a compound represented by the formula (i-7) is added is taken as Example 62.
  • a liquid crystal composition containing a polymerizable compound to which 0.1 parts by mass of a compound represented by the formula (i-14) is added is set as an example 63.
  • a liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of a compound represented by the formula (i-1) was taken as example 64.
  • Example 65 0.8 parts by mass of the spontaneously orienting compound (AL 2.25), 0.3 parts by mass of the compound represented by the formula (RM-R1), and 100 parts by mass of the liquid crystal composition LC-1
  • a liquid crystal composition containing a polymerizable compound to which 0.3 parts by mass of a compound represented by the formula (i-2) is added is taken as Example 65.
  • Example 66 0.8 parts by mass of the spontaneously orienting compound (AL 2.25), 0.3 parts by mass of the compound represented by the formula (RM-R1), and 100 parts by mass of the liquid crystal composition LC-1
  • a liquid crystal composition containing a polymerizable compound to which 0.3 parts by mass of a compound represented by the formula (i-6) is added is taken as Example 66.
  • Example 67 A liquid crystal composition containing a polymerizable compound to which 0.3 parts by mass of a compound represented by the formula (i-7) is added is taken as Example 67.
  • Example 68 A liquid crystal composition containing a polymerizable compound to which 0.3 parts by mass of a compound represented by the formula (i-14) is added is taken as Example 68.
  • Example 69 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.17), 0.4 parts by mass of the formula (AL-2.17), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by -R2) and 0.4 parts by mass of the compound represented by the formula (i-1) is set as Example 69.
  • Example 70 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.17), 0.4 parts by mass of the formula (AL-2.25), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by -R2) and 0.4 parts by mass of the compound represented by the formula (i-2) was used as Example 70.
  • Example 71 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.17), 0.4 parts by mass of the formula (AL-2.29), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.4 parts by mass of the compound represented by the formula (i-6) was prepared as Example 71.
  • Example 72 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.17), 0.4 parts by mass of the formula (AL-1.15), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.4 parts by mass of the compound represented by the formula (i-7) is set as Example 72.
  • Example 73 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.17), 0.4 parts by mass of the formula (AL-1.10), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.4 parts by mass of the compound represented by the formula (i-14) is set as Example 73.
  • Example 74 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.29), 0.4 parts by mass of the formula (AL-2.17), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.6 parts by mass of the compound represented by the formula (i-1) was prepared as Example 74.
  • Example 75 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.29), 0.4 parts by mass of the formula (AL-2.25), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by -R2) and 0.6 parts by mass of the compound represented by the formula (i-2) was used as Example 75.
  • Example 76 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.29), 0.4 parts by mass of the formula (AL-2.17), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.6 parts by mass of the compound represented by the formula (i-6) was prepared as Example 76.
  • Example 77 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.29), 0.4 parts by mass of the formula (AL-1.15), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.6 parts by mass of the compound represented by the formula (i-7) is set as Example 77.
  • Example 78 100 parts by mass of the liquid crystal composition LC-1, 0.4 parts by mass of the spontaneously displacing compound formula (AL-2.29), 0.4 parts by mass of the formula (AL-1.10), the formula (RM A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 parts by mass of the compound represented by —R2) and 0.6 parts by mass of the compound represented by the formula (i-14) is set as Example 78.
  • compositions composed of compounds and mixing ratios as shown in the following 17 are prepared, and liquid crystal compositions are LC-2 To LC-8.
  • liquid crystal compositions LC-2 to LC-8 were mixed with the spontaneous orientation compound and the polymerizable compound at appropriate concentrations shown in Examples 1 to 78 and Comparative Examples 1 to 4, respectively, in the same manner as above.
  • the evaluation of the orientation test was carried out, and it was confirmed that the compositions of the examples were improved in orientation as compared with the comparative examples.

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