Liquid crystal composition containing polymerizable compound and liquid crystal display element using the same

Abstract

The present invention provides a liquid crystal composition containing a polymerizable compound, and a liquid crystal display device using the same. The liquid crystal composition containing a polymerizable compound can provide a liquid crystal display device with a low residual monomer content, good voltage holding ratio (VHR), good pretilt angle formation, and good low-temperature storage properties. The liquid crystal composition containing a polymerizable compound and a liquid crystal display device using the same include one or more polymerizable compounds represented by general formula (i), one or more sensitizing compounds, and one or more liquid crystal compounds.

Description

Technical Field

[0001] The present invention relates to a liquid crystal composition containing a polymerizable compound and a liquid crystal display element using the same. Background Art

[0002] Liquid crystal display element is with clock, desk calculator as the beginning, gradually used for various measuring equipment, automobile with panel, word processor, electronic notepad, printer, computer, television, clock, advertising display board etc.As liquid crystal display mode, as its representative mode, can enumerate twisted nematic (Twisted Nematic, TN) type, super twisted nematic (SuperTwisted Nematic, STN) type, the vertical alignment (Vertical Alignment, VA) type or plane switching (In-Plane Switching, IPS) type etc. of thin film transistor (Thin Film Transistor, TFT) etc. are used.It is required that the liquid crystal composition used in these liquid crystal display elements is stable to external factors such as moisture, air, heat, light, and, in the widest possible temperature range centered on room temperature, liquid crystal phase, viscosity are low and driving voltage is low.In order to make dielectric constant anisotropy (Δε) or refractive index anisotropy (Δn) etc. be the most suitable value for each liquid crystal display element, liquid crystal composition is made up of several to tens of compounds.

[0003] VA-type displays use liquid crystal compositions with a negative Δε and are widely used in LCD televisions (TVs). Among these, the polymer sustained alignment (PSA) mode polymerizes monomers dissolved in the liquid crystal, imparting a desired pretilt angle to the vertically aligned liquid crystal molecules. This mode has become the mainstream in current LCD TVs due to its ability to achieve a wider viewing angle, high-speed response, and high transmittance.

[0004] Furthermore, in recent years, there has been a demand for further high-speed response of liquid crystal display elements, and liquid crystal compositions have been required to have extremely high characteristics that are completely different from those in conventional technologies (Patent Documents 1 and 2).

[0005] [Prior art literature]

[0006] [Patent Document]

[0007] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-112192

[0008] [Patent Document 2] Japanese Patent Application Laid-Open No. 2010-285499 Summary of the Invention

[0009] [Problems to be solved by the invention]

[0010] However, liquid crystal compositions are susceptible to degradation due to active energy rays such as light emitted from backlight sources or ultraviolet rays irradiated during the manufacturing process of liquid crystal display elements. Impurities generated by light degradation of the liquid crystal composition can cause a decrease in the voltage holding ratio (VHR) of the liquid crystal panel. Therefore, there is a demand for a liquid crystal composition that can maintain a high voltage holding ratio (VHR) even when achieving high-speed response.

[0011] The problem to be solved by the present invention is to provide a liquid crystal composition having a low residual monomer content, a high voltage holding ratio (VHR), good pretilt angle formation and low-temperature storage properties, and a liquid crystal display element using the same.

[0012] [Technical means to solve the problem]

[0013] The present inventors have conducted diligent research and found that the above-mentioned problems can be solved by comprising a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i) described later, one or more sensitizing compounds, and one or more liquid crystal compounds, thereby completing the present invention.

[0014] The present invention for solving the above-mentioned problems has the following configuration.

[0015] The liquid crystal composition containing a polymerizable compound of the present invention comprises at least:

[0016] One or more polymerizable compounds represented by the following general formula (i);

[0017] one or more sensitizing compounds; and

[0018] One or more liquid crystal compounds,

[0019] [Chemistry 1]

[0020]

[0021] (Where,

[0022] P i1 and P i2 Each independently represents a polymerizable group,

[0023] Sp i1 and Sp i2 represents a single bond or an alkylene group having 1 to 20 carbon atoms,

[0024] One or more -CH2- in the alkylene group may be independently substituted by -O- or -NH-.

[0025] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0026] One or more hydrogen atoms in the alkylene group may be independently substituted by halogen atoms.

[0027] Oxygen atoms do not bond directly to each other.

[0028] A i1 、A i2 and A i3 Each independently represents any one of a divalent aromatic group, a divalent cycloaliphatic group, and a divalent heterocyclic compound group,

[0029] A i1 、A i2 and A i3 One or more hydrogen atoms in the can be substituted independently by Sr i1 replace,

[0030] Substituent Sr i1 represents any one of a halogen atom and an alkyl group having 1 to 20 carbon atoms,

[0031] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0032] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0033] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0034] Oxygen atoms do not bond directly to each other.

[0035] In the presence of multiple substituents Sr i1 In the case of , they may be the same or different,

[0036] Sp i1 、Sp i2 and / or substituent Sr i1 at least one of represents an alkylene group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms,

[0037] In Sp i1 、Sp i2 and / or substituent Sr i1 At least one of the alkylene groups having 1 to 20 carbon atoms or the alkyl groups having 1 to 20 carbon atoms represented by

[0038] One or more -CH2- and / or

[0039] One or more hydrogen atoms in the group are independently selected from the following formula (PG i -1)~Formula(PG i -33) is substituted by a group consisting of a group represented by

[0040] [Chemistry 2]

[0041]

[0042] [Chemistry 3]

[0043]

[0044] [Chemistry 4]

[0045]

[0046] (Formula (PG i -1)~Formula(PG i -33),

[0047] X PGi and Z PGi Each independently represents a methylene group (-CH2-), an oxygen atom (-O-) or a sulfur atom (-S-),

[0048] Y PGi represents a carbonyl group (>C=O), a sulfinyl group (>C=S), an oxygen atom (—O—) or a sulfur atom (—S—),

[0049] W PGi represents a methylene group (-CH2-), a carbonyl group (>C=O) or a sulfinyl group (>C=S),

[0050] S PGi 、T PGi and U PGi Each independently represents a methine group (=CH-) or a nitrogen atom (=N-),

[0051] In the formula (PG i -18), S PGi and T PGi Not simultaneously represent methine (=CH-),

[0052] In the formula (PG i -19), S PGi 、T PGi and U PGi Not simultaneously represent methine (=CH-),

[0053] R PGieach independently represents an alkyl group having 1 to 20 carbon atoms,

[0054] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0055] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0056] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0057] Oxygen atoms do not bond directly to each other.

[0058] In the presence of multiple R PGi In the case of , they may be the same or different,

[0059] Sp PGi each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms,

[0060] One or more -CH2- in the alkylene group or the arylene group may be independently substituted by -O- or -NH-.

[0061] One or more -CH2-CH2- in the alkylene group or the arylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0062] One or more hydrogen atoms in the alkylene group or the arylene group may be independently substituted by a halogen atom or a hydroxyl group.

[0063] Oxygen atoms do not bond directly to each other.

[0064] In the presence of multiple Sp PGi In the case of , they may be the same or different,

[0065] * indicates a bonding bond,

[0066] wherein one or more -CH2- in the group is selected from the free formula (PG i -1)~Formula(PG i -7) is substituted by a group consisting of a group represented by

[0067] One or more hydrogen atoms in the group are selected from the formula (PG i -8)~Formula(PG i -33) is substituted with a group consisting of a group represented by

[0068] L i1 and L i2 Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms,

[0069] One or more hydrogen atoms in the alkylene group may be independently substituted by a halogen atom or an alkyl group having 1 to 6 carbon atoms.

[0070] n i1 represents an integer from 0 to 1,

[0071] In the presence of multiple L i2 、A i3 In the case of , they may be the same or different)

[0072] Furthermore, the liquid crystal display element of the present invention uses the liquid crystal composition containing the polymerizable compound.

[0073] Furthermore, an example of the structure of the present invention is as follows.

[0074] Item 1. A liquid crystal composition containing a polymerizable compound, comprising at least:

[0075] One or more polymerizable compounds represented by the following general formula (i);

[0076] one or more sensitizing compounds; and

[0077] One or more liquid crystal compounds,

[0078] [Chemistry 5]

[0079]

[0080] (Where,

[0081] P i1 and P i2 Each independently represents a polymerizable group,

[0082] Sp i1 and Sp i2 represents a single bond or an alkylene group having 1 to 20 carbon atoms,

[0083] One or more -CH2- in the alkylene group may be independently substituted by -O- or -NH-.

[0084] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0085] One or more hydrogen atoms in the alkylene group may be independently substituted by halogen atoms.

[0086] Oxygen atoms do not bond directly to each other.

[0087] A i1 、A i2 and A i3 Each independently represents any one of a divalent aromatic group, a divalent cycloaliphatic group, and a divalent heterocyclic compound group,

[0088] A i1 、A i2 and A i3 One or more hydrogen atoms in the can be substituted independently by Sr i1 replace,

[0089] Substituent Sr i1 represents any one of a halogen atom and an alkyl group having 1 to 20 carbon atoms,

[0090] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0091] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0092] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0093] Oxygen atoms do not bond directly to each other.

[0094] In the presence of multiple substituents Sr i1 In the case of , they may be the same or different,

[0095] Sp i1 、Sp i2 and / or substituent Sr i1 at least one of represents an alkylene group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms,

[0096] In Sp i1 、Sp i2 and / or substituent Sr i1 At least one of the alkylene groups having 1 to 20 carbon atoms or the alkyl groups having 1 to 20 carbon atoms represented by

[0097] One or more -CH2- and / or

[0098] One or more hydrogen atoms in the group are independently selected from the following formula (PG i -1)~Formula(PG i -33) is substituted by a group consisting of a group represented by

[0099] [Chemistry 6]

[0100]

[0101] [Chemistry 7]

[0102]

[0103] [Chemistry 8]

[0104]

[0105] (Formula (PG i -1)~Formula(PG i -33),

[0106] X PGi and Z PGi Each independently represents a methylene group (-CH2-), an oxygen atom (-O-) or a sulfur atom (-S-),

[0107] Y PGi represents a carbonyl group (>C=O), a sulfinyl group (>C=S), an oxygen atom (—O—) or a sulfur atom (—S—),

[0108] W PGi represents a methylene group (-CH2-), a carbonyl group (>C=O) or a sulfinyl group (>C=S),

[0109] S PGi 、T PGi and U PGi Each independently represents a methine group (=CH-) or a nitrogen atom (=N-),

[0110] In the formula (PG i -18), S PGi and T PGi Not simultaneously represent methine (=CH-),

[0111] In the formula (PG i -19), S PGi 、T PGi and U PGi Not simultaneously represent methine (=CH-),

[0112] R PGi each independently represents an alkyl group having 1 to 20 carbon atoms,

[0113] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0114] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0115] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0116] Oxygen atoms do not bond directly to each other.

[0117] In the presence of multiple R PGi In the case of , they may be the same or different,

[0118] Sp PGi each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms,

[0119] One or more -CH2- in the alkylene group or the arylene group may be independently substituted by -O- or -NH-.

[0120] One or more -CH2-CH2- in the alkylene group or the arylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0121] One or more hydrogen atoms in the alkylene group or the arylene group may be independently substituted by a halogen atom or a hydroxyl group.

[0122] Oxygen atoms do not bond directly to each other.

[0123] In the presence of multiple Sp PGi In the case of , they may be the same or different,

[0124] * indicates a bonding bond,

[0125] wherein one or more -CH2- in the group is selected from the free formula (PG i -1)~Formula(PG i -7) is substituted by a group consisting of a group represented by

[0126] One or more hydrogen atoms in the group are selected from the formula (PG i -8)~Formula(PG i -33) is substituted with a group consisting of a group represented by

[0127] L i1 and L i2 Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms,

[0128] One or more hydrogen atoms in the alkylene group may be independently substituted by a halogen atom or an alkyl group having 1 to 6 carbon atoms.

[0129] n i1 represents an integer from 0 to 1,

[0130] In the presence of multiple L i2 、A i3 In the case of , they may be the same or different)

[0131] Item 2. The liquid crystal composition containing a polymerizable compound according to Item 1, wherein the liquid crystal composition containing a polymerizable compound according to the formula (PG i -1) is substituted with a group represented by

[0132] Item 3. The liquid crystal composition containing a polymerizable compound according to Item 1 or 2, wherein the Sp i2 It represents an alkylene group having 1 to 20 carbon atoms.

[0133] Item 4. The liquid crystal composition containing a polymerizable compound according to any one of Items 1 to 3, wherein the n i1 is 0.

[0134] Item 5. The liquid crystal composition containing a polymerizable compound according to any one of Items 1 to 4, wherein the L i1 For a single bond.

[0135] Item 6. The liquid crystal composition containing a polymerizable compound according to any one of Items 1 to 5, wherein the divalent aromatic group represents any one of 1,4-phenylene, naphthalene-2,6-diyl, anthracene-2,6-diyl, phenanthrene-2,7-diyl, indan-2,5-diyl, and 1,2,3,4-tetrahydronaphthalene-2,6-diyl.

[0136] The divalent cyclic aliphatic group represents any one of 1,4-cyclohexylene, 1,4-cyclohexenylene, and 1,3-dioxane-2,5-diyl.

[0137] The divalent heterocyclic compound group represents any one of a pyridine-2,5-diyl group and a pyrimidine-2,5-diyl group.

[0138] Item 7. The liquid crystal composition containing a polymerizable compound according to any one of Items 1 to 6, wherein the sensitizing compound is a compound represented by the following general formula (SC):

[0139] [Chemistry 9]

[0140]

[0141] (In formula (SC),

[0142] R SC1and R SC2 each independently represents an alkyl group having 1 to 20 carbon atoms,

[0143] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0144] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0145] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0146] Oxygen atoms do not bond directly to each other.

[0147] S SC2 、S SC3 、S SC5 and S SC6 each independently represents a hydrogen atom or a fluorine atom,

[0148] A SC1 Each independently represents a group selected from the group consisting of the following groups (a) and (b):

[0149] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups present in the group may be substituted with -O- and / or -S-),

[0150] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in the group may be substituted with -N=)

[0151] The A SC1 One or more hydrogen atoms in the can be substituted independently by Sr SC1 replace,

[0152] Substituent Sr SC1 represents any one of a halogen atom and an alkyl group having 1 to 20 carbon atoms,

[0153] One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-.

[0154] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0155] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0156] Oxygen atoms do not bond directly to each other.

[0157] In the presence of multiple substituents Sr SC1 In the case of , they may be the same or different,

[0158] n SC1 Integer from 0 to 1)

[0159] Item 8. The polymerizable compound-containing liquid crystal composition according to any one of Items 1 to 7, further comprising a polymerizable compound having a structure different from that of general formula (i).

[0160] Item 9. The liquid crystal composition containing a polymerizable compound according to any one of Items 1 to 8, wherein the liquid crystal compound comprises a compound selected from the group consisting of compounds represented by any one of the following general formulas (NU-01) to (NU-08),

[0161] [Chemistry 10]

[0162]

[0163] (In general formulas (NU-01) to (NU-08),

[0164] R NU1 and R NU2 Each independently represents any one of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms,

[0165] One or more -CH2-CH2- in the group may be independently replaced by -C≡C-, -CO-, -CO-O- or -O-CO-.

[0166] Oxygen atoms are not directly bonded to each other)

[0167] Item 10. A liquid crystal display element comprising two substrates, and

[0168] A liquid crystal layer is included between the two substrates, the liquid crystal layer comprising the liquid crystal composition containing a polymerizable compound according to any one of items 1 to 9,

[0169] The liquid crystal display element contains a polymer obtained by polymerizing the polymerizable compound represented by the general formula (i).

[0170] [Effects of the Invention]

[0171] According to the present invention, by using a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i) described later, one or more sensitizing compounds, and one or more liquid crystal compounds, a liquid crystal display element with a low residual monomer content, good voltage holding ratio (VHR), formation of a pretilt angle, and low-temperature storage properties can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0172] Figure 1 This is an exploded perspective view showing an example of the liquid crystal display element of the present invention.

[0173] [Explanation of Symbols]

[0174] 1: Liquid crystal display element

[0175] 2: First substrate

[0176] 3: Second substrate

[0177] 4: Liquid crystal layer

[0178] 5: Pixel electrode layer

[0179] 6: Transparent electrode layer (common electrode layer)

[0180] 7: First polarizer

[0181] 8: Second polarizer

[0182] 9: Color filter / color filter layer DETAILED DESCRIPTION

[0183] (Polymerizable compound represented by general formula (i))

[0184] The polymerizable compound-containing liquid crystal composition of the present invention contains one or two or more polymerizable compounds represented by the following general formula (i).

[0185] [Chemistry 11]

[0186]

[0187] The polymerizable compound represented by general formula (i) has a polar group in its structure.

[0188] That is, in the general formula (i), Sp described later i1 、Sp i2 and / or substituent Sr i1 At least one of represents an alkylene group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, in Sp i1 、Sp i2 and / or substituent Sr i1In at least one of the alkylene groups having 1 to 20 carbon atoms or the alkyl groups having 1 to 20 carbon atoms represented by , one or more -CH2- in the group and / or one or more hydrogen atoms in the group are independently selected from the following formula (PG i -1)~Formula(PG i -33) is substituted by a group selected from the group consisting of the groups represented by

[0189] [Chemistry 12]

[0190]

[0191] [Chemistry 13]

[0192]

[0193] [Chemistry 14]

[0194]

[0195] wherein one or more -CH2- in the group is selected from the free formula (PG i -1)~Formula(PG i -7) is substituted by a group consisting of a group represented by a group, wherein one or more hydrogen atoms in the group are selected from the group consisting of a group represented by a group of formula (PG i -8)~Formula(PG i -33) is substituted by a group selected from the group consisting of the groups represented by

[0196] Formula (PG i -1)~Formula(PG i -33) in X PGi and Z PGi Each independently represents a methylene group (—CH 2 —), an oxygen atom (—O—) or a sulfur atom (—S—).

[0197] In addition, the formula (PG i -1)~Formula(PG i -33), Y PGi represents a carbonyl group (>C=O), a sulfinyl group (>C=S), an oxygen atom (—O—) or a sulfur atom (—S—).

[0198] In addition, the formula (PG i -1)~Formula(PG i -33) in W PGi represents a methylene group (-CH2-), a carbonyl group (>C=O) or a sulfinyl group (>C=S).

[0199] In addition, the formula (PG i -1)~Formula(PG i -33), SPGi 、T PGi and U PGi Each independently represents a methine group (=CH-) or a nitrogen atom (=N-).

[0200] Among them, in the formula (PG i -18), S PGi and T PGi It does not represent a methine group (=CH-) at the same time.

[0201] In addition, in the formula (PG i -19), S PGi 、T PGi and U PGi It does not represent a methine group (=CH-) at the same time.

[0202] Formula (PG i -1)~Formula(PG i -33), R PGi Each independently represents an alkyl group having 1 to 20 carbon atoms.

[0203] One or more -CH2- groups in the alkyl group may be independently substituted by -O- or -NH-.

[0204] In addition, one or two or more -CH2-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0205] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0206] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0207] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0208] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0209] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0210] For example, R PGi When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0211] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0212] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0213] In addition, R PGi When one or two or more -CH2-CH2- in the alkyl group are replaced by -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0214] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0215] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0216] In addition, R PGi When one or two or more -CH2-CH2- in the alkyl group are substituted with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0217] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0218] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0219] In addition, R PGi When one -CH2- in the alkyl group is substituted by -O-, and one or more -CH2-CH2- are substituted by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0220] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0221] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0222] In addition, R PGi When one or two or more hydrogen atoms in the alkyl group are replaced by halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0223] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0224] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0225] In addition, R PGi When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0226] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0227] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0228] As R PGi Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: PGi -1)~Formula(R PGi -31) represented by the base, etc.

[0229] [Chemistry 15]

[0230]

[0231] Formula (R PGi -1)~Formula(R PGi -31), black dots represent bonding bonds.

[0232] As R PGi , preferably a linear alkyl group having 1 to 6 carbon atoms.

[0233] In the presence of multiple R PGi In the case of , they may be the same or different.

[0234] Formula (RG i -1)~Formula(RG i -33), Sp PGi Each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms.

[0235] One or two or more -CH2- groups in the alkylene group or the arylene group may be independently substituted by -O- or -NH-.

[0236] In addition, one or two or more -CH2-CH2- groups in the alkylene group or the arylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O-, or -O-CO-.

[0237] In addition, one or two or more hydrogen atoms in the alkylene group or the arylene group may be independently substituted with a halogen atom or a hydroxyl group.

[0238] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0239] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0240] The alkylene group having 1 to 20 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0241] The number of carbon atoms in the alkylene group having 1 to 20 carbon atoms is preferably 1 to 12, preferably 1 to 9, and more preferably 1 to 6.

[0242] The arylene group having 6 to 20 carbon atoms is a linear, branched or cyclic arylene group, and is preferably a linear arylene group.

[0243] The arylene group having 6 to 20 carbon atoms preferably has 6 to 12 carbon atoms, more preferably 6 to 9 carbon atoms.

[0244] As Sp PGi Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) and the arylene group having 6 to 20 carbon atoms (including substituted arylene groups) in the formula (Sp PGi -1)~Formula(Sp PGi -14) represented by the base, etc.

[0245] [Chemistry 16]

[0246]

[0247] Formula (Sp PGi -1)~Formula(Sp PGi -14), a white dot indicates a bond to an oxygen atom or a sulfur atom, and an * indicates a bond to a carbon atom, a nitrogen atom, or a silicon atom.

[0248] As Sp PGi , preferably a linear alkylene group having 1 to 6 carbon atoms.

[0249] In the presence of multiple Sp PGi In the case of , they may be the same or different.

[0250] Formula (PG i -1)~Formula(PG i -33), * represents a bonding bond.

[0251] As the formula (PG i Specific examples of the group represented by -1) include the formula (PG i -1-1)~Formula(PG i -1-3) represented by the group.

[0252] [Chemistry 17]

[0253]

[0254] Formula (PG i -1-1)~Formula(PGi -1-3), * represents a bonding bond.

[0255] As the formula (PG i Specific examples of the group represented by -2) include the formula (PG i -2-1)~Formula(PG i -2-3) represented by the group.

[0256] [Chemistry 18]

[0257]

[0258] Formula (PG i -2-1)~Formula(PG i -2-3), * represents a bonding bond.

[0259] As the formula (PG i Specific examples of the group represented by -3) include the formula (PG i -3-1) represented by the group.

[0260] [Chemistry 19]

[0261]

[0262] Formula (PG i -3-1), * represents a bonding bond.

[0263] As the formula (PG i Specific examples of the group represented by -4) include the formula (PG i -4-1) represented by the group.

[0264] [Chemistry 20]

[0265]

[0266] Formula (PG i -4-1), * represents a bonding bond.

[0267] As the formula (PG i Specific examples of the group represented by -5) include the formula (PG i -5-1) represented by the group.

[0268] [Chemistry 21]

[0269]

[0270] Formula (PG i -5-1), * represents a bonding bond.

[0271] As the formula (PG i Specific examples of the group represented by -6) include the formula (PGi -6-1) represented by the group.

[0272] [Chemistry 22]

[0273]

[0274] Formula (PG i -6-1), * represents a bonding bond.

[0275] As the formula (PG i Specific examples of the group represented by -7) include the formula (PG i -7-1) represented by the group.

[0276] [Chemistry 23]

[0277]

[0278] Formula (PG i -7-1), * represents a bonding bond.

[0279] As the formula (PG i Specific examples of the group represented by (PG i -13-1) represented by the group.

[0280] [Chemistry 24]

[0281]

[0282] Formula (PG i -13-1), * represents a bonding bond.

[0283] As the formula (PG i Specific examples of the group represented by (PG i -15-1) represented by the group.

[0284] [Chemistry 25]

[0285]

[0286] Formula (PG i -15-1), * represents a bonding bond.

[0287] As the formula (PG i Specific examples of the group represented by (PG i -16-1) represented by the group.

[0288] [Chemistry 26]

[0289]

[0290] Formula (PGi -16-1), * represents a bonding bond.

[0291] As the formula (PG i Specific examples of the group represented by -17) include the formula (PG i -17-1)~Formula(PG i -17-3) represented by the group.

[0292] [Chemistry 27]

[0293]

[0294] Formula (PG i -17-1)~Formula(PG i -17-3), * represents a bonding bond.

[0295] As the formula (PG i Specific examples of the group represented by (PG i -18-1)~Formula(PG i -18-2) represented by the group.

[0296] [Chemistry 28]

[0297]

[0298] Formula (PG i -18-1)~Formula(PG i -18-2), * represents a bonding bond.

[0299] As the formula (PG i Specific examples of the group represented by (PG i -19-1)~Formula(PG i -19-3) represented by the group.

[0300] [Chemistry 29]

[0301]

[0302] Formula (PG i -19-1)~Formula(PG i -19-3), * represents a bonding bond.

[0303] As the formula (PG i Specific examples of the group represented by (PG i -20-1)~Formula(PG i -20-3) represented by the group.

[0304] [Chemistry 30]

[0305]

[0306] Formula (PG i -20-1)~Formula(PG i -20-3), * represents a bonding bond.

[0307] As the formula (PG i Specific examples of the group represented by -21) include the formula (PG i -21-1)~Formula(PG i -21-2) represented by the group.

[0308] [Chemistry 31]

[0309]

[0310] Formula (PG i -21-1)~Formula(PG i -21-2), * represents a bonding bond.

[0311] As the formula (PG i Specific examples of the group represented by -22) include the formula (PG i -22-1) represented by the group.

[0312] [Chemistry 32]

[0313]

[0314] Formula (PG i -22-1), * represents a bonding bond.

[0315] As the formula (PG i Specific examples of the group represented by (PG i -23-1)~Formula(PG i -23-2) represented by the group.

[0316] [Chemistry 33]

[0317]

[0318] Formula (PG i -23-1)~Formula(PG i -23-2), * represents a bonding bond.

[0319] As the formula (PG i Specific examples of the group represented by (PG i -31-1) represented by the group.

[0320] [Chemistry 34]

[0321]

[0322] Formula (PG i -31-1), * represents a bonding bond.

[0323] As the formula (PG i Specific examples of the group represented by (PG i -32-1) represented by the base.

[0324] [Chemistry 35]

[0325]

[0326] Formula (PG i -32-1), * represents a bonding bond.

[0327] As the formula (PG i Specific examples of the group represented by (PG i -33-1) represented by the group.

[0328] [Chemistry 36]

[0329]

[0330] Formula (PG i -33-1), * represents a bonding bond.

[0331] From the viewpoint of improving voltage holding ratio and solubility, the polymerizable compound represented by general formula (i) is preferably a polymerizable compound of formula (PG i -1) is substituted, more preferably by the formula (PG i -1-3) is substituted with a group represented by

[0332] In the general formula (i), P i1 and P i2 Each independently represents a polymerizable group.

[0333] The polymerizable group is, for example, a group suitable for chain polymerization such as radical polymerization, cationic polymerization, or anionic polymerization, and / or stepwise polymerization such as addition polymerization or condensation polymerization.

[0334] The polymerizable group is preferably a group containing an n-membered ring structure (n represents an integer of 3 to 7) having a carbon-carbon double bond (>C=C<), a carbon-carbon triple bond (-C≡C-), and / or an oxygen atom as a constituent member.

[0335] In addition, the polymerizable group is preferably selected from the group consisting of i1 / 2 -1)~Formula(P i1 / 2 -8) in the group.

[0336] [Chemistry 37]

[0337]

[0338] Formula (P i1 / 2 -1)~Formula(P i1 / 2 -8), S i1 / 2 Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms.

[0339] Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, and a propyl group.

[0340] Examples of the halogenated alkyl group having 1 to 5 carbon atoms include trifluoromethyl and difluoroethyl.

[0341] As S i1 / 2 , preferably each independently represents a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

[0342] Formula (P i1 / 2 -1)~Formula(P i1 / 2 -8), the black dots represent the Sp i1 or Sp i2 The bond key.

[0343] From the perspective of ensuring appropriate responsiveness, P i1 and P i2 Preferably, the formula (P i1 / 2 -1), formula (P i1 / 2 -2), formula (P i1 / 2 -3), formula (P i1 / 2 -4), formula (P i1 / 2- 5) or formula (P i1 / 2 -7), preferably the formula (P i1 / 2 -1), formula (P i1 / 2 -2), formula (P i1 / 2 -3) or formula (P i1 / 2 -7), preferably the formula (P i1 / 2 -1), preferably an acrylic acid group (formula (P i1 / 2 -1), S i1 / 2 = hydrogen atom) or methacrylic acid group (formula (P i1 / 2 -1), S i1 / 2 = methyl), preferably methacrylic acid.

[0344] In addition, P i1 and P i2 Can be the same or different.

[0345] In addition, in P i1 and P i2 Select the same formula (Pi1 / 2 -1)~Formula(P i1 / 2 -8), the same symbols (S i1 / 2 ) may be the same or different.

[0346] In the general formula (i), Sp i1 and Sp i2 Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms.

[0347] One or two or more -CH2- groups in the alkylene group may be independently substituted by -O- or -NH-.

[0348] In addition, one or two or more -CH2-CH2- groups in the alkylene group may be substituted by -CH=CH-, -C≡C-, -CO-O-, or -O-CO-.

[0349] In addition, one or two or more hydrogen atoms in the alkylene group may be independently substituted with a halogen atom.

[0350] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0351] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0352] The alkylene group having 1 to 20 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0353] The number of carbon atoms in the alkylene group having 1 to 20 carbon atoms is preferably 1 to 12, preferably 1 to 9, and more preferably 1 to 6.

[0354] As Sp i1 and Sp i2 Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: i1 / 2 -1)~Formula(Sp i1 / 2 -5) represented by the base, etc.

[0355] [Chemistry 38]

[0356]

[0357] Formula (Sp i1 -1)~Formula(Sp i1 -5), the white dot indicates the i1 or P i2 The bond of A i1 、A i2 or A i3 The bond key.

[0358] In addition, preferably Sp i2 It represents an alkylene group having 1 to 20 carbon atoms.

[0359] In addition, Sp i2 Preferably, it is a linear alkylene group having 1 to 6 carbon atoms or a linear alkyleneoxy group having 1 to 6 carbon atoms.

[0360] As P i1 -Sp i1 - and P i2 -Sp i2 -Specific examples include the formula (P i1 / 2 -Sp i1 / 2 -1)~Formula(P i1 / 2 -Sp i1 / 2 -19) represented by the base, etc.

[0361] [Chemistry 39]

[0362]

[0363] [Chemistry 40]

[0364]

[0365] Formula (P i1 / 2 -Sp i1 / 2 -1)~Formula(P i1 / 2 -Sp i1 / 2 -19), * indicates that A i1 、A i2 or A i3 The bond key.

[0366] In the general formula (i), A i1 、A i2 and A i3 Each independently represents any one of a divalent aromatic group, a divalent cycloaliphatic group, and a divalent heterocyclic compound group.

[0367] Examples of the divalent aromatic group include 1,4-phenylene, naphthalene-2,6-diyl, anthracene-2,6-diyl, phenanthrene-2,7-diyl, indan-2,5-diyl, and 1,2,3,4-tetrahydronaphthalene-2,6-diyl.

[0368] Examples of the divalent cyclic aliphatic group include a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, and a 1,3-dioxane-2,5-diyl group.

[0369] Examples of the divalent heterocyclic compound group include a pyridine-2,5-diyl group and a pyrimidine-2,5-diyl group.

[0370] A i1 、Ai2 and A i3 One or more hydrogen atoms in the can be substituted independently by Sr i1 replace.

[0371] Substituent Sr i1 It represents any one of a halogen atom and an alkyl group having 1 to 20 carbon atoms.

[0372] One or more -CH2- groups in the alkyl group may be independently substituted by -O- or -NH-.

[0373] In addition, one or two or more -CH2-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0374] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0375] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0376] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0377] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0378] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0379] For example, the substituent Sr i1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0380] The alkoxy group having 1 to 19 carbon atoms is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0381] The number of carbon atoms in the alkoxy group having 1 to 19 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0382] In addition, the substituent Sr i1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxyalkyl group having 1 to 19 carbon atoms can be represented.

[0383] The alkoxyalkyl group having 1 to 19 carbon atoms is a linear, branched or cyclic alkoxyalkyl group, and is preferably a linear alkoxyalkyl group.

[0384] The number of carbon atoms in the alkoxyalkyl group having 1 to 19 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0385] In addition, the substituent Sr i1 When one or two or more hydrogen atoms in the alkyl group are independently substituted with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0386] The halogenated alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0387] The number of carbon atoms in the halogenated alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0388] Substituent Sr i1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0389] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0390] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0391] As a substituent Sr i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: i1 -1)~Formula(Sr i1 -21) represented by the base, etc.

[0392] [Chemistry 41]

[0393]

[0394] Formula (Sr i1 -1)~Formula(Sr i1 -21), the black dot indicates the i1 、A i2 or A i3 The bond key.

[0395] In the presence of multiple substituents Sr i1 In the case of , they may be the same or different.

[0396] As A i1 The substituent Sr i1 The substitution position is preferably the following formula (A i1 -SP-1)~Formula (A i1 -SP-3).

[0397] [Chemistry 42]

[0398]

[0399] Formula (A i1 -SP-1)~Formula (A i1 -SP-3), the white dot represents Sp i1 The black dot indicates the bond to L i1 The bond key.

[0400] As A i2 The substituent Sr i1 The substitution position is preferably the following formula (A i2 -SP-1)~Formula (A i2 -SP-2).

[0401] [Chemistry 43]

[0402]

[0403] Formula (A i2 -SP-1)~Formula (A i2 -SP-2), the white dot indicates the L i1 The black dot indicates the bond to L i2 or Sp i2 The bond key.

[0404] As A i3 The substituent Sr i1 The substitution position is preferably the following formula (A i3 -SP-1)~Formula (A i3 -SP-2).

[0405] [Chemistry 44]

[0406]

[0407] Formula (A i3 -SP-1)~Formula (A i3 -SP-2), the white dot indicates the L i2 The black dots represent the bonds to Sp i2 The bond key.

[0408] More specifically, A is preferred i1 Represents the following formula (A i1 -1)~Formula (A i1 -5) any one.

[0409] [Chemistry 45]

[0410]

[0411] Formula (A i1 -1)~Formula (A i1 -5), the white dot indicates the Sp i1 The black dot indicates the bond to L i1 The bond key.

[0412] More specifically, A is preferred i2 Represents the following formula (A i2 -1)~Formula (A i2 -6).

[0413] [Chemistry 46]

[0414]

[0415] Formula (A i2 -1)~Formula (A i2 -6), the white dot indicates the L i1 The black dot indicates the bond to L i2 or Sp i2 The bond key.

[0416] More specifically, A is preferred i3 Represents the following formula (A i3 -1)~Formula (A i3 -4) any one.

[0417] [Chemistry 47]

[0418]

[0419] Formula (A i3 -1)~Formula (A i3 -4), the white dot indicates the L i2 The black dots represent the bonds to Sp i2 The bond key.

[0420] In the general formula (i), L i1 and L i2 Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms.

[0421] One or two or more hydrogen atoms in the alkylene group may be independently substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms.

[0422] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0423] The alkylene group having 1 to 20 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0424] The number of carbon atoms in the alkylene group having 1 to 20 carbon atoms is preferably 1 to 15, more preferably 1 to 10.

[0425] As L i1 and L i2 Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: i1 / 2 -1)~Formula(L i1 / 2 -2) The base represented by

[0426] [Chemistry 48]

[0427]

[0428] Formula (L i1 / 2 -1)~Formula(L i1 / 2 -2), the white dot indicates the i1 or A i2 The black dot indicates the bond to A i2 or A i3 The bond key.

[0429] In addition, L i1 It is preferably a single bond.

[0430] In the general formula (i), n i1 It represents an integer from 0 to 1, and is preferably 0.

[0431] In the presence of multiple L i2 、A i3 In the case of , they may be the same or different.

[0432] The polymerizable compound represented by the general formula (i) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (i-1) to (i-13).

[0433] [Chemistry 49]

[0434]

[0435] [Chemistry 50]

[0436]

[0437] In general formulas (i-1) to (i-13), P i1 、P i2 、Sp i1 and Sp i2 and Sr i1 Each independently represents P in the general formula (i) i1 、P i2 、Sp i1 and Spi2 and Sr i1 Same meaning respectively.

[0438] Specific examples of the compound represented by General Formula (i-1) include compounds represented by the following structural formulas (i-1-1) to (i-1-16).

[0439] [Chemistry 51]

[0440]

[0441] [Chemistry 52]

[0442]

[0443] [Chemistry 53]

[0444]

[0445] Specific examples of the compound represented by general formula (i-2) include compounds represented by the following structural formulas (i-2-1) to (i-2-9).

[0446] [Chemistry 54]

[0447]

[0448] [Chemistry 55]

[0449]

[0450] Specific examples of the compound represented by General Formula (i-3) include compounds represented by the following Structural Formulas (i-3-1) to (i-3-12).

[0451] [Chemistry 56]

[0452]

[0453] [Chemistry 57]

[0454]

[0455] Specific examples of the compound represented by General Formula (i-4) include compounds represented by the following structural formulas (i-4-1) to (i-4-15).

[0456] [Chemistry 58]

[0457]

[0458] [Chemistry 59]

[0459]

[0460] [Chemistry 60]

[0461]

[0462] Specific examples of the compound represented by General Formula (i-5) include compounds represented by the following Structural Formulas (i-5-1) to (i-5-12).

[0463] [Chemistry 61]

[0464]

[0465] [Chemistry 62]

[0466]

[0467] Specific examples of the compound represented by General Formula (i-6) include compounds represented by the following structural formulas (i-6-1) to (i-6-12).

[0468] [Chemistry 63]

[0469]

[0470] [Chemistry 64]

[0471]

[0472] Specific examples of the compound represented by general formula (i-7) include compounds represented by the following structural formulas (i-7-1) to (i-7-6).

[0473] [Chemistry 65]

[0474]

[0475] Specific examples of the compound represented by General Formula (i-8) include compounds represented by the following Structural Formulas (i-8-1) to (i-8-4).

[0476] [Chemistry 66]

[0477]

[0478] Specific examples of the compound represented by General Formula (i-9) include compounds represented by the following structural formulas (i-9-1) to (i-9-8).

[0479] [Chemistry 67]

[0480]

[0481] [Chemistry 68]

[0482]

[0483] Specific examples of the compound represented by General Formula (i-10) include compounds represented by the following Structural Formulas (i-10-1) to (i-10-4).

[0484] [Chemistry 69]

[0485]

[0486] Specific examples of the compound represented by General Formula (i-11) include compounds represented by the following structural formulas (i-11-1) to (i-11-8).

[0487] [Chemistry 70]

[0488]

[0489] [Chemistry 71]

[0490]

[0491] Specific examples of the compound represented by General Formula (i-12) include compounds represented by the following Structural Formulas (i-12-1) to (i-12-4).

[0492] [Chemistry 72]

[0493]

[0494] Specific examples of the compound represented by General Formula (i-13) include compounds represented by the following Structural Formulas (i-13-1) to (i-13-4).

[0495] [Chemistry 73]

[0496]

[0497] General formula (i), general formula (i-1) to general formula (i-13), structural formula (i-1-1) to structural formula (i-1-16), structural formula (i-2-1) to structural formula (i-2-9), structural formula (i-3-1) to structural formula (i-3-12), structural formula (i-4-1) to structural formula (i-4-15), structural formula (i-5-1) to structural formula (i-5-12), structural formula (i-6-1) to structural formula (i-6-12), structural formula (i-7-1) to structural formula (i-7-6), structural formula (i-8-1) to structural formula (i-8- 4), the types of polymerizable compounds represented by structural formula (i-9-1) to structural formula (i-9-8), structural formula (i-10-1) to structural formula (i-10-4), structural formula (i-11-1) to structural formula (i-11-8), structural formula (i-12-1) to structural formula (i-12-4) or structural formula (i-13-1) to structural formula (i-13-4) used in the liquid crystal composition containing the polymerizable compound are one or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two, and preferably one.

[0498] General formula (i), general formula (i-1) to general formula (i-13), structural formula (i-1-1) to structural formula (i-1-16), structural formula (i-2-1) to structural formula (i-2-9), structural formula (i-3-1) to structural formula (i-3-12), structural formula (i-4-1) to structural formula (i-4-15), structural formula (i-5-1) to structural formula (i-5-12), structural formula (i-6-1) to structural formula (i-6-12), structural formula (i-7-1) to structural formula (i-7-6), structural formula (i-8-1) to structural formula (i-8-1) 8-4), structural formula (i-9-1) to structural formula (i-9-8), structural formula (i-10-1) to structural formula (i-10-4), structural formula (i-11-1) to structural formula (i-11-8), structural formula (i-12-1) to structural formula (i-12-4) or structural formula (i-13-1) to structural formula (i-13-4) in 100 mass% of the liquid crystal composition containing the polymerizable compound has a lower limit value of the total content of 0.01 mass% or more, preferably 0.05 mass% or more, and preferably 1.0 mass% or more.

[0499] General formula (i), general formula (i-1) to general formula (i-13), structural formula (i-1-1) to structural formula (i-1-16), structural formula (i-2-1) to structural formula (i-2-9), structural formula (i-3-1) to structural formula (i-3-12), structural formula (i-4-1) to structural formula (i-4-15), structural formula (i-5-1) to structural formula (i-5-12), structural formula (i-6-1) to structural formula (i-6-12), structural formula (i-7-1) to structural formula (i-7-6), structural formula (i-8-1) to structural formula (i -8-4), structural formula (i-9-1) to structural formula (i-9-8), structural formula (i-10-1) to structural formula (i-10-4), structural formula (i-11-1) to structural formula (i-11-8), structural formula (i-12-1) to structural formula (i-12-4) or structural formula (i-13-1) to structural formula (i-13-4) in 100% by mass of a liquid crystal composition containing polymerizable compounds has an upper limit value of preferably less than 1.0% by mass, preferably less than 0.7% by mass, and preferably less than 0.5% by mass.

[0500] From the viewpoint of achieving both high voltage holding ratio (VHR) and low temperature storage stability, general formula (i), general formula (i-1) to general formula (i-13), structural formula (i-1-1) to structural formula (i-1-16), structural formula (i-2-1) to structural formula (i-2-9), structural formula (i-3-1) to structural formula (i-3-12), structural formula (i-4-1) to structural formula (i-4-15), structural formula (i-5-1) to structural formula (i-5-12), structural formula (i-6-1) to structural formula (i-6-12), structural formula (i-7-1) to structural formula (i-7-6), structural formula (i-8-1 ) to Structural Formula (i-8-4), Structural Formula (i-9-1) to Structural Formula (i-9-8), Structural Formula (i-10-1) to Structural Formula (i-10-4), Structural Formula (i-11-1) to Structural Formula (i-11-8), Structural Formula (i-12-1) to Structural Formula (i-12-4) or Structural Formula (i-13-1) to Structural Formula (i-13-4) in 100 mass% of the liquid crystal composition containing the polymerizable compound has a total content of preferably 0.01 mass% to 1.0 mass%, preferably 0.05 mass% to 0.7 mass%, and preferably 0.1 mass% to 0.5 mass%.

[0501] The polymerizable compound represented by the general formula (i) (including subordinate concepts) can be synthesized using a known synthesis method.

[0502] (Sensitizing compound)

[0503] The polymerizable compound-containing liquid crystal composition of the present invention contains one or two or more sensitizing compounds.

[0504] A sensitizing compound is a compound that, through its sensitizing effect, enables a polymerizable compound to polymerize more quickly and fully. The use of a sensitizing compound allows the polymerizable compound to polymerize more quickly, thereby enabling the formation of a large pretilt even with weak ultraviolet (UV) light or a small amount of UV light, and also achieving high pretilt stability. Furthermore, the rapid polymerization allows for a shorter UV irradiation time, thereby suppressing degradation of the liquid crystal composition caused by UV irradiation and reducing the reduction in voltage holding ratio (VHR).

[0505] As the sensitizing compound, a naphthalene compound is preferred, and a sensitizing compound represented by the following general formula (SC) is more preferred.

[0506] [Chemistry 74]

[0507]

[0508] In the general formula (SC), R SC1 and R SC2 Each independently represents an alkyl group having 1 to 20 carbon atoms.

[0509] One or more -CH2- groups in the alkyl group may be independently substituted by -O- or -NH-.

[0510] In addition, one or two or more -CH2-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0511] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0512] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0513] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0514] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0515] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0516] For example, R SC1 and R SC2When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0517] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0518] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0519] In addition, R SC1 and R SC2 When one or two or more -CH2-CH2- in the alkyl group are replaced by -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0520] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0521] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0522] In addition, R SC1 and R SC2 When one or two or more -CH2-CH2- in the alkyl group are substituted with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0523] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0524] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0525] In addition, R SC1 and R SC2 When one -CH2- in the alkyl group is substituted by -O-, and one or more -CH2-CH2- are substituted by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0526] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0527] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0528] In addition, R SC1 and R SC2 When one or two or more hydrogen atoms in the alkyl group are replaced by halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0529] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0530] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0531] In addition, R SC1 and R SC2 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0532] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0533] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0534] As R SC1 and R SC2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: SC1 / 2 -1)~Formula(R SC1 / 2 -31) represented by the base, etc.

[0535] [Chemistry 75]

[0536]

[0537] Formula (R SC1 / 2 -1)~Formula(R SC1 / 2- 21), the black dots represent 2,6-naphthalene-2,4-phenylene or A SC1 The bond key.

[0538] In the general formula (SC), S SC2 、S SC3 、S SC5 and S SC6 Each independently represents a hydrogen atom (H) or a fluorine atom (F).

[0539] As S SC2 、S SC3 、S SC5 and S SC6 Combination of (S SC2 、S SC3 、S SC5 、S SC6 ), preferably (H, H, H, H), (F, H, H, H), (H, F, H, H) or (F, F, H, H).

[0540] In the general formula (SC), A SC1 Each independently represents a group selected from the group consisting of the following groups (a) and (b):

[0541] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-);

[0542] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in the group may be substituted with -N=)

[0543] The A SC1 One or more hydrogen atoms in the can be substituted independently by Sr SC1 replace.

[0544] Substituent Sr SC1 It represents a halogen atom or an alkyl group having 1 to 20 carbon atoms.

[0545] One or more -CH2- groups in the alkyl group may be independently substituted by -O- or -NH-.

[0546] In addition, one or two or more -CH2-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0547] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0548] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0549] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0550] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0551] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0552] For example, the substituent Sr SC1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0553] The alkoxy group having 1 to 19 carbon atoms is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0554] The number of carbon atoms in the alkoxy group having 1 to 19 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0555] In addition, the substituent Sr SC1When one -CH2- in the alkyl group is replaced by -O-, an alkoxyalkyl group having 1 to 19 carbon atoms can be represented.

[0556] The alkoxyalkyl group having 1 to 19 carbon atoms is a linear, branched or cyclic alkoxyalkyl group, and is preferably a linear alkoxyalkyl group.

[0557] The number of carbon atoms in the alkoxyalkyl group having 1 to 19 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0558] In addition, the substituent Sr SC1 When one or two or more hydrogen atoms in the alkyl group are independently substituted with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0559] The halogenated alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0560] The number of carbon atoms in the halogenated alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0561] Substituent Sr SC1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0562] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0563] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0564] As a substituent Sr SC1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: SC1 -1)~Formula(Sr SC1 -21) represented by the base, etc.

[0565] [Chemistry 76]

[0566]

[0567] Formula (Sr SC1 -1)~Formula(Sr SC1 -21), the black dot indicates the SC1 The bond key.

[0568] As a substituent Sr SC1 , preferably a halogen atom, preferably a fluorine atom.

[0569] In the presence of multiple substituents Sr SC1 In the case of , they may be the same or different.

[0570] As A SC1 The substituent Sr SC1 The substitution position is preferably the following formula (A SC1 -SP-1)~Formula (A SC1 -SP-3).

[0571] [Chemistry 77]

[0572]

[0573] Formula (A SC1 -SP-1)~Formula (A SC1 -SP-3), the white dots represent the bonding to 1,4-phenylene, and the black dots represent the bonding to R SC2 The bond key.

[0574] More specifically, A is preferred SC1 Represents the following formula (A SC1 -1)~Formula (A SC1 -3) any one.

[0575] [Chemistry 78]

[0576]

[0577] Formula (A SC1 -1)~Formula (A SC1 -3), the white dots represent the bonding bonds to 1,4-phenylene, and the black dots represent the bonding bonds to R SC2 The bond key.

[0578] In the general formula (SC), n SC1 It represents an integer from 0 to 1, and is preferably 0.

[0579] The polymerizable compound represented by General Formula (SC) is preferably a compound selected from the group consisting of compounds represented by the following General Formulas (SC-1) to (SC-14).

[0580] [Chemistry 79]

[0581]

[0582] In the general formulas (SC-1) to (SC-7), R SC1 and R SC2 Each independently represents R in the general formula (SC) SC1 and R SC2 Same meaning respectively.

[0583] Specific examples of the compound represented by General Formula (SC-1) include compounds represented by the following structural formula (SC-1-1).

[0584] [Chemistry 80]

[0585]

[0586] Specific examples of the compound represented by General Formula (SC-4) include compounds represented by the following Structural Formula (SC-4-1).

[0587] [Chemistry 81]

[0588]

[0589] The sensitizing compound represented by general formula (SC), general formula (SC-1) to general formula (SC-7), structural formula (SC-1-1) or structural formula (SC-4-1) is used in a liquid crystal composition containing a polymerizable compound at one or more types, preferably one to five types, preferably one to four types, preferably one to three types, preferably one to two types, and preferably one type.

[0590] The lower limit of the total content of the sensitizing compounds represented by General Formula (SC), General Formula (SC-1) to General Formula (SC-7), Structural Formula (SC-1-1) or Structural Formula (SC-4-1) in 100 mass % of the liquid crystal composition containing the polymerizable compound is preferably 0.01 mass % or more, preferably 0.03 mass % or more, preferably 0.04 mass % or more, and preferably 0.05 mass % or more.

[0591] The upper limit of the total content of the sensitizing compounds represented by General Formula (SC), General Formula (SC-1) to General Formula (SC-7), Structural Formula (SC-1-1) or Structural Formula (SC-4-1) in 100 mass % of the liquid crystal composition containing the polymerizable compound is preferably 0.25 mass % or less, preferably 0.2 mass % or less, and preferably 0.15 mass % or less.

[0592] From the perspective of achieving both high voltage holding ratio (VHR) and monomer reactivity, the total content of the sensitizing compounds represented by general formula (SC), general formula (SC-1) to general formula (SC-7), structural formula (SC-1-1) or structural formula (SC-4-1) in 100 mass% of the liquid crystal composition containing the polymerizable compound is preferably 0.01 mass% to 0.25 mass%, preferably 0.03 mass% to 0.2 mass%, preferably 0.04 mass% to 0.15 mass%, and preferably 0.05 mass% to 0.15 mass%.

[0593] The sensitizing compound represented by the general formula (SC) (including subordinate concepts) can be synthesized using a known synthesis method.

[0594] (Polymerizable liquid crystal compound having a structure different from that of general formula (i))

[0595] The polymerizable compound-containing liquid crystal composition of the present invention may contain one or two or more polymerizable compounds having a structure different from that of general formula (i).

[0596] For example, as a polymerizable compound having a structure different from that of the general formula (i), a polymerizable compound represented by the following general formula (ii) and the like can be cited.

[0597] [Chemistry 82]

[0598]

[0599] In the general formula (ii), R ii1 、R ii2 、R ii3 、R ii4 、R ii5 、R ii6 、R ii7 and R ii8 Each independently represents an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom, P ii3 -Sp ii3 - or any of hydrogen atoms.

[0600] Examples of the alkyl group having 1 to 18 carbon atoms include linear, branched, and cyclic groups. From the viewpoint of obtaining good orientation, a linear group is preferred.

[0601] The number of carbon atoms in the alkyl group having 1 to 18 carbon atoms is preferably 1 to 3 when solubility in a liquid crystal composition containing a polymerizable compound is important, and preferably 10 to 18 when vertical alignment of the liquid crystal composition containing a polymerizable compound is important.

[0602] Examples of the alkoxy group having 1 to 18 carbon atoms include linear, branched, and cyclic groups. From the viewpoint of obtaining good orientation, a linear group is preferred.

[0603] The number of carbon atoms in the alkoxy group having 1 to 18 carbon atoms is preferably 1 to 3 when solubility in a liquid crystal composition containing a polymerizable compound is important, and preferably 10 to 18 when vertical alignment of the liquid crystal composition containing a polymerizable compound is important.

[0604] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0605] From the viewpoint of ensuring compatibility with the liquid crystal compound, R ii1 、R ii2 、R ii5 、R ii6 and R ii8 At least one of them is preferably a halogen atom, more preferably a fluorine atom.

[0606] In the general formula (ii), P ii1 、P ii2 and P ii3 Each independently represents a polymerizable group.

[0607] The polymerizable group is, for example, a group suitable for chain polymerization such as radical polymerization, cationic polymerization, or anionic polymerization, and / or stepwise polymerization such as addition polymerization or condensation polymerization.

[0608] The polymerizable group is preferably a group containing an n-membered ring structure (n represents an integer of 3 to 7) having a carbon-carbon double bond (>C=C<), a carbon-carbon triple bond (-C≡C-), and / or an oxygen atom as a constituent member.

[0609] In addition, the polymerizable group is preferably selected from the following general formula (P ii1 / 2 / 3 -1)~General formula (P ii1 / 2 / 3 -8) in the group.

[0610] [Chemistry 83]

[0611]

[0612] General formula (P ii1 / 2 / 3 -1)~General formula (P ii1 / 2 / 3 -8), S ii1 / 2 / 3 Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms.

[0613] Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, and a propyl group.

[0614] Examples of the halogenated alkyl group having 1 to 5 carbon atoms include a trifluoromethyl group and a difluoroethyl group.

[0615] As S ii1 / 2 / 3 , preferably each independently represents a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

[0616] General formula (P ii1 / 2 / 3 -1)~General formula (P ii1 / 2 / 3 -8), * indicates Sp ii1 、Sp ii2 or Sp ii3 The key node.

[0617] From the perspective of ensuring appropriate reactivity, Pii1 、P ii2 and P ii3 Preferably, the formula (P ii1 / 2 / 3 -1), formula (P ii1 / 2 / 3 -2), formula (P ii1 / 2 / 3 -3), formula (P ii1 / 2 / 3 -4), formula (P ii1 / 2 / 3 -5) or formula (P ii1 / 2 / 3 -7), preferably the formula (P ii1 / 2 / 3 -1), formula (P ii1 / 2 / 3 -2), formula (P ii1 / 2 / 3 -3) or formula (P ii1 / 2 / 3 -7), preferably the formula (P ii1 / 2 / 3 -1), preferably an acrylic acid group (formula (P ii1 / 2 / 3 -1), S ii1 / 2 / 3 = hydrogen atom) or methacrylic acid group (formula (P ii1 / 2 / 3 -1), S ii1 / 2 / 3 = methyl), preferably methacrylic acid.

[0618] In addition, P ii1 、P ii2 and P ii3 Can be the same or different, P ii1 and P ii2 Preferably they are the same.

[0619] In addition, in P ii1 、P ii2 and P ii3 Select the same formula (P ii1 / 2 / 3 -1)~Formula(P ii1 / 2 / 3 -8), the same symbols (S ii1 / 2 / 3 ) may be the same or different.

[0620] Furthermore, from the viewpoint of compatibility with liquid crystal compounds, in the polymerizable compound represented by the general formula (ii), R ii1 、R ii2 、R ii3 、R ii4 、R ii5 、R ii6 、R ii7 and R ii8 are not hydrogen atoms, preferably R ii1 、R ii2 、R ii3 、R ii4 、R ii5 、R ii6 、R ii7 and R ii8At least one of them represents a halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, or P ii3 -Sp ii3 -.

[0621] In the general formula (ii), Sp ii1 、Sp ii2 and Sp ii3 Each independently represents a single bond or a spacer.

[0622] The spacer group is a group having flexibility.

[0623] More specifically, the spacer represents an alkylene group having 1 to 15 carbon atoms.

[0624] One or two or more -CH2- groups in the alkylene group may be independently substituted by -O-.

[0625] In addition, one or two or more -CH2-CH2- groups in the alkylene group may be independently substituted by -O-CO- or -CO-O-.

[0626] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0627] In addition, Sp ii1 、Sp ii2 and Sp ii3 Can be the same or different.

[0628] The alkylene group having 1 to 15 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0629] The number of carbon atoms in the alkylene group having 1 to 15 carbon atoms is preferably 1 to 8, more preferably 1 to 4, and more preferably 2 to 3.

[0630] More specifically, Sp ii1 、Sp ii2 and Sp ii3 Preferably, each independently represents a single bond, -CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -O-, -CH2-O-, -CH2-CH2-O-, or -CH2-CO-O-.

[0631] In addition, Sp ii1 and Sp ii2 Both are preferably single bonds.

[0632] In the general formula (ii), L ii1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0633] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0634] The number of carbon atoms in the alkylene group is preferably 2 to 10, more preferably 2 to 6.

[0635] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0636] In addition, one or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0637] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0638] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted alkylene groups) include the following: ii1 -1)~Formula(L ii1 -24) represented by the base, etc.

[0639] [Chemistry 84]

[0640]

[0641] Formula (L ii1 -1)~Formula(L ii1 -24), white and black dots represent the bonding of p-1,4-phenylene.

[0642] In the general formula (ii), n ii1 Indicates an integer from 1 to 2.

[0643] In n ii1 In the case of 2, there are multiple R ii5 、R ii6 、R ii7 and R ii8 , L ii1 They may be the same as or different from each other.

[0644] Preferred examples of the polymerizable compound represented by the general formula (ii) include compounds represented by the following general formulas (ii-1) to (ii-3).

[0645] [Chemistry 85]

[0646]

[0647] In the general formulas (ii-1) to (ii-3), Sp ii1 、Sp ii2 、R ii6 and R ii7 Represents Sp in the general formula (ii) ii1 、Sp ii2 、R ii6 and R ii7 Same meaning.

[0648] Specific examples of the polymerizable compound represented by the general formula (ii-1) include polymerizable compounds represented by the following structural formulas (ii-1-1) to (ii-1-4).

[0649] [Chemistry 86]

[0650]

[0651] Specific examples of the polymerizable compound represented by the general formula (ii-2) include polymerizable compounds represented by the following structural formulas (ii-2-1) to (ii-1-2).

[0652] [Chemistry 87]

[0653]

[0654] Specific examples of the polymerizable compound represented by the general formula (ii-3) include polymerizable compounds represented by the following structural formula (ii-3-1).

[0655] [Chemistry 88]

[0656]

[0657] The type of polymerizable compound represented by general formula (ii), general formula (ii-1) to general formula (ii-3), structural formula (ii-1-1) to structural formula (ii-1-4), structural formula (ii-2-1) to structural formula (ii-2-2) or structural formula (ii-3-1) used in the liquid crystal composition containing the polymerizable compound is preferably one or more types, preferably one to five types, preferably one to four types, preferably one to three types, preferably one to two types, and preferably one type.

[0658] The lower limit of the total content of the polymerizable compounds represented by general formula (ii), general formula (ii-1) to general formula (ii-3), structural formula (ii-1-1) to structural formula (ii-1-4), structural formula (ii-2-1) to structural formula (ii-2-2) or structural formula (ii-3-1) in 100 mass% of the liquid crystal composition containing the polymerizable compounds is preferably 0.1 mass% or more, preferably 0.15 mass% or more, and preferably 0.2 mass% or more.

[0659] The upper limit value of the total content of the polymerizable compounds represented by general formula (ii), general formula (ii-1) to general formula (ii-3), structural formula (ii-1-1) to structural formula (ii-1-4), structural formula (ii-2-1) to structural formula (ii-2-2) or structural formula (ii-3-1) in 100 mass% of the liquid crystal composition containing the polymerizable compounds is preferably 1.0 mass% or less, preferably 0.7 mass% or less, and preferably 0.5 mass% or less.

[0660] The total content of the polymerizable compounds represented by general formula (ii), general formula (ii-1) to general formula (ii-3), structural formula (ii-1-1) to structural formula (ii-1-4), structural formula (ii-2-1) to structural formula (ii-2-2) or structural formula (ii-3-1) in 100 mass% of the liquid crystal composition containing the polymerizable compounds is preferably 0.1 mass% to 1.0 mass%, preferably 0.15 mass% to 0.7 mass%, and preferably 0.2 mass% to 0.5 mass%.

[0661] The polymerizable compound represented by the general formula (ii) (including subordinate concepts) can be synthesized using a known synthesis method.

[0662] (Liquid Crystal Composition Containing a Polymerizable Compound)

[0663] The liquid crystal composition containing a polymerizable compound of the present invention can be produced by mixing, for example, a polymerizable compound represented by the general formula (i), a sensitizing compound (SC), a liquid crystal composition used in the liquid crystal composition containing a polymerizable compound, a polymerizable compound having a structure different from that of the general formula (i) as required, and additives.

[0664] The liquid crystal composition used in the liquid crystal composition containing a polymerizable compound contains one or two or more liquid crystal compounds.

[0665] (Liquid Crystal Compound)

[0666] Examples of liquid crystal compounds include those having negative dielectric anisotropy at 20°C (Δε<-2), those having neutral dielectric anisotropy at 20°C (-2≦Δε≦2), and those having positive dielectric anisotropy at 20°C (2<Δε).

[0667] The dielectric anisotropy (Δε) of the liquid crystal compound is a value obtained by extrapolating the dielectric anisotropy of a composition obtained by adding the liquid crystal compound to a composition having substantially neutral dielectric properties at 20°C.

[0668] In addition, the liquid crystal compound preferably does not include a naphthalene ring structure in its structure.

[0669] That is, the liquid crystal compound is preferably not a naphthalene compound.

[0670] The liquid crystal compound having negative dielectric anisotropy (Δε<-2) at 20° C. is preferably a compound selected from the group consisting of liquid crystal compounds represented by any one of the following general formulae (N-01) to (N-05).

[0671] [Chemistry 89]

[0672]

[0673] In the general formulas (N-01) to (N-05), R N1 and R N2 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms.

[0674] One or more -CH2- groups in the group may be independently substituted by -C≡C-, -CO-, -CO-O- or -O-CO-.

[0675] However, when the group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0676] R N1 An alkyl group having 1 to 8 carbon atoms is preferred, an alkyl group having 1 to 5 carbon atoms is preferred, and an alkyl group having 2 to 4 carbon atoms is preferred.

[0677] Among them, in Z N1 When R represents other than a single bond, N1 An alkyl group having 1 to 3 carbon atoms is preferred.

[0678] R N2An alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferred, an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms is preferred, and an alkoxy group having 1 to 4 carbon atoms is preferred.

[0679] Examples of the alkenyl group having 2 to 8 carbon atoms include formula (R1) to formula (R7), and preferably formula (R1) or formula (R2).

[0680] [Chemistry 90]

[0681]

[0682] In formulae (R1) to (R7), black dots represent bonds to the ring structure.

[0683] In the general formulas (N-01) to (N-05), Z N1 Each independently represents a single bond, -CH2-CH2-, -O-CH2-, -CH2-O-, -CO-O-, -O-CO-, -O-CF2-, -CF2-O-, -CH=CH-, -CF=CF- or -C≡C-.

[0684] In the general formulas (N-01) to (N-05), m N1 Each independently represents 1 or 2.

[0685] When m N1 When Z is 1, 1 Preferred is a single bond or -CH2-O-.

[0686] When m N1 When Z is 2, 1 Preferred is a single bond, -CH2-CH2- or -CH2-O-.

[0687] The hydrogen atoms present on the rings of the liquid crystal compounds represented by General Formulae (N-01) to (N-05) may each independently be substituted with a fluorine atom or a chlorine atom.

[0688] The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds selected from the group consisting of compounds represented by general formulae (N-01-1) to (N-01-4) as the compound represented by general formula (N-01).

[0689] [Chemistry 91]

[0690]

[0691] In the general formulas (N-01-1) to (N-01-4), R N3 and R N4Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0692] Examples of the liquid crystal compound represented by General Formula (N-01-1) include liquid crystal compounds represented by the following structural formulas (N-01-1.1) to (N-01-1.2).

[0693] [Chemistry 92]

[0694]

[0695] Examples of the liquid crystal compound represented by General Formula (N-01-2) include liquid crystal compounds represented by the following structural formulas (N-01-2.1) to (N-01-2.5).

[0696] [Chemistry 93]

[0697]

[0698] Examples of the liquid crystal compound represented by the general formula (N-01-3) include liquid crystal compounds represented by the following structural formulas (N-01-3.1) to (N-01-3.3).

[0699] [Chemistry 94]

[0700]

[0701] Examples of the liquid crystal compound represented by the general formula (N-01-4) include liquid crystal compounds represented by the following structural formulas (N-01-4.1) to (N-01-4.4).

[0702] [Chemistry 95]

[0703]

[0704] The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds selected from the group consisting of compounds represented by general formulae (N-02-1) to (N-02-3) as the compound represented by general formula (N-02).

[0705] [Chemistry 96]

[0706]

[0707] In the general formulas (N-02-1) to (N-02-3), R N3 Each independently represents an alkyl group having 1 to 5 carbon atoms.

[0708] In the general formulas (N-02-1) to (N-02-3), R N4 Each independently represents an alkoxy group having 1 to 4 carbon atoms.

[0709] Examples of the liquid crystal compound represented by General Formula (N-02-1) include liquid crystal compounds represented by the following structural formula (N-02-1.1).

[0710] [Chemistry 97]

[0711]

[0712] The liquid crystal compound represented by the general formula (N-03) in the polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or two or more liquid crystal compounds represented by the general formula (N-03-1).

[0713] [Chemistry 98]

[0714]

[0715] In the general formula (N-03-1), R N3 It represents an alkyl group having 1 to 5 carbon atoms.

[0716] In the general formula (N-03-1), R N4 It represents an alkoxy group having 1 to 4 carbon atoms.

[0717] Examples of the liquid crystal compound represented by the general formula (N-03-1) include liquid crystal compounds represented by the following structural formulas (N-03-1.1) to (N-03-1.5).

[0718] [Chemistry 99]

[0719]

[0720] The liquid crystal compound represented by the general formula (N-04) in the polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or two or more liquid crystal compounds represented by the general formula (N-04-1).

[0721] [Chemistry 100]

[0722]

[0723] In the general formula (N-04-1), R N3 It represents an alkyl group having 1 to 5 carbon atoms.

[0724] In the general formula (N-04-1), R N4 It represents an alkoxy group having 1 to 4 carbon atoms.

[0725] Examples of the liquid crystal compound represented by General Formula (N-04-1) include liquid crystal compounds represented by the following structural formulas (N-04-1.1) to (N-04-1.3).

[0726] [Chemistry 101]

[0727]

[0728] The polymerizable compound-containing liquid crystal composition of the present invention may contain, as the compound represented by general formula (N-05), a liquid crystal compound selected from the group consisting of compounds represented by structural formulas (N-05-1) to (N-05-2).

[0729] [Chemistry 102]

[0730]

[0731] General formula (N-01) to general formula (N-05), general formula (N-01-1) to general formula (N-01-4), general formula (N-02-1) to general formula (N-02-3), general formula (N-03-1), general formula (N-04-1), structural formula (N-01-1.1) to structural formula (N-01-1.2), structural formula (N-01-2.1) to structural formula (N-01-2.5), structural formula (N-01-3.1) to structural formula (N-01-3.3), structural formula (N-01-4.1) to structural formula The types of liquid crystal compounds represented by formula (N-01-4.4), formula (N-02-1.1), formula (N-03-1.1) to formula (N-03-1.5), formula (N-04-1.1) to formula (N-04-1.3) or formula (N-05-1) to formula (N-05-2) used in the liquid crystal composition containing the polymerizable compound are preferably one to fifteen types, preferably one to thirteen types, preferably two to thirteen types, preferably two to eleven types, and preferably two to eight types.

[0732] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-01), general formula (N-01-1) to general formula (N-01-4), structural formula (N-01-1.1) to structural formula (N-01-1.2), structural formula (N-01-2.1) to structural formula (N-01-2.5), structural formula (N-01-3.1) to structural formula (N-01-3.3) or structural formula (N-01-4.1) to structural formula (N-01-4.4) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, and 80 mass%.

[0733] The preferred upper limit value of the total content of the liquid crystal compounds represented by general formula (N-01), general formula (N-01-1) to general formula (N-01-4), structural formula (N-01-1.1) to structural formula (N-01-1.2), structural formula (N-01-2.1) to structural formula (N-01-2.5), structural formula (N-01-3.1) to structural formula (N-01-3.3) or structural formula (N-01-4.1) to structural formula (N-01-4.4) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass% and 10 mass%.

[0734] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-02), general formula (N-02-1) to general formula (N-02-3) or structural formula (N-02-1.1) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, and 80 mass%.

[0735] The preferred upper limit value of the total content of the liquid crystal compounds represented by general formula (N-02), general formula (N-02-1) to general formula (N-02-3) or structural formula (N-02-1.1) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, and 10 mass%.

[0736] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-03), general formula (N-03-1) or structural formula (N-03-1.1) to structural formula (N-03-1.5) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 15 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, and 80 mass%.

[0737] The preferred upper limit value of the total content of the liquid crystal compounds represented by general formula (N-03), general formula (N-03-1) or structural formula (N-03-1.1) to structural formula (N-03-1.5) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, and 10 mass%.

[0738] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-04), general formula (N-04-1) or structural formula (N-04-1.1) to structural formula (N-04-1.3) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass%, 1 mass%, 5 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, and 80 mass%.

[0739] The preferred upper limit value of the total content of the liquid crystal compounds represented by general formula (N-04), general formula (N-04-1) or structural formula (N-04-1.1) to structural formula (N-04-1.2) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass%, 15 mass%, and 10 mass%.

[0740] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-05) or structural formula (N-05-1) to structural formula (N-05-2) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass%, 2 mass%, 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, and 20 mass%.

[0741] The preferred upper limit values ​​of the total content of liquid crystal compounds represented by general formula (N-05) or structural formula (N-05-1) to structural formula (N-05-2) in 100 mass% of a liquid crystal composition containing a polymerizable compound are 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, and 13 mass%.

[0742] The liquid crystal compound having a neutral dielectric anisotropy at 20° C. (−2≦Δε≦2) is preferably a compound selected from the group consisting of liquid crystal compounds represented by any one of the following general formulae (NU-01) to (NU-08).

[0743] [Chemistry 103]

[0744]

[0745] In the general formulas (NU-01) to (NU-08), R NU1 and R NU2 Each independently represents any one of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms.

[0746] One or more -CH2-CH2- groups in the group may be independently substituted by -C≡C-, -CO-, -CO-O- or -O-CO-.

[0747] However, when the group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0748] As R NU1 and R NU2 , preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and preferably an alkyl group having 1 to 5 carbon atoms.

[0749] In addition, when the purpose is to achieve high-speed response, in the general formula (NU-01), R NU1 is an alkenyl group having 2 to 3 carbon atoms, R NU2 An alkyl group having 1 to 6 carbon atoms is included in the liquid crystal composition containing a polymerizable compound of the present invention, which ensures high-speed response. This is because the compound has low viscosity or low rotational viscosity, which significantly contributes to both improved reliability and improved responsiveness.

[0750] In more detail, R NU1 Particularly preferred is an alkyl group having 1 to 5 carbon atoms, R NU2 Particularly preferred are an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

[0751] Examples of the alkenyl group having 2 to 3 carbon atoms include formula (R1) and formula (R2), and formula (R1) or formula (R2) is preferred.

[0752] [Chemistry 104]

[0753]

[0754] In formulae (R1) and (R2), black dots represent bonds to the ring structure.

[0755] Examples of the liquid crystal compound represented by General Formula (NU-01) include liquid crystal compounds represented by the following structural formulas (NU-01-1) to (NU-01-6).

[0756] [Chemistry 105]

[0757]

[0758] Examples of the liquid crystal compound represented by General Formula (NU-02) include liquid crystal compounds represented by the following structural formulas (NU-02-1) and (NU-02-2).

[0759] [Chemistry 106]

[0760]

[0761] Examples of the liquid crystal compound represented by the general formula (NU-03) include liquid crystal compounds represented by the following structural formulas (NU-03-1) to (NU-03-4).

[0762] [Chemistry 107]

[0763]

[0764] Examples of the liquid crystal compound represented by General Formula (NU-04) include liquid crystal compounds represented by the following structural formulas (NU-04-1) and (NU-04-2).

[0765] [Chemistry 108]

[0766]

[0767] Examples of the liquid crystal compound represented by the general formula (NU-05) include liquid crystal compounds represented by the following structural formulas (NU-05-1) to (NU-05-4).

[0768] [Chemistry 109]

[0769]

[0770] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-01) or structural formulas (NU-01-1) to (NU-01-6) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 15 mass% to 55 mass%, 20 mass% to 50 mass%, and 25 mass% to 45 mass%.

[0771] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-02) or structural formula (NU-02-1) to structural formula (NU-02-2) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass% to 30 mass%, 0.5 mass% to 25 mass%, and 1 mass% to 20 mass%.

[0772] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-03) or structural formulas (NU-03-1) to (NU-03-4) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass% to 25 mass%, 1 mass% to 20 mass%, and 3 mass% to 15 mass%.

[0773] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-04) or structural formula (NU-04-1) to structural formula (NU-04-2) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass% to 25 mass%, 0.5 mass% to 15 mass%, and 1 mass% to 10 mass%.

[0774] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-05) or structural formulas (NU-05-1) to (NU-05-4) in 100 mass% of the liquid crystal composition containing the polymerizable compound is 0 mass% to 30 mass%, 1 mass% to 25 mass%, and 3 mass% to 20 mass%.

[0775] The total content of the liquid crystal compound represented by general formula (NU-06) in 100% by mass of the liquid crystal composition containing the polymerizable compound is preferably in the range of 0% to 30% by mass, preferably 0% to 20% by mass, and preferably 0% to 10% by mass.

[0776] The total content of the liquid crystal compound represented by general formula (NU-07) in 100% by mass of the liquid crystal composition containing the polymerizable compound is preferably in the range of 0% to 30% by mass, preferably 0% to 20% by mass, and preferably 0% to 10% by mass.

[0777] The total content of the liquid crystal compound represented by general formula (NU-08) in 100% by mass of the liquid crystal composition containing the polymerizable compound is preferably in the range of 0% to 30% by mass, preferably 0% to 20% by mass, and preferably 0% to 10% by mass.

[0778] The liquid crystal compound having a positive dielectric anisotropy at 20° C. (2<Δε) is preferably a compound selected from the group consisting of liquid crystal compounds represented by any one of the following general formulae (P-01) to (P-02).

[0779] [Chemistry 110]

[0780]

[0781] In general formulas (P-01) to (P-02), R P11 Each independently represents any one of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, and an alkenyloxy group having 2 to 8 carbon atoms. P11 , preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group having 3 carbon atoms (propenyl).

[0782] When reliability is important, R P11 An alkyl group is preferred. When the viscosity reduction is important, R P11 Preferred is alkenyl.

[0783] In addition, in R P11 When the bonded ring structure is a phenyl group (aromatic), it is preferably any one of a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms. P11 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms. To stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0784] Examples of the alkenyl group having 2 to 8 carbon atoms include groups represented by formulae (R1) to (R7), and are preferably groups represented by formula (R1) or (R2).

[0785] [Chemistry 111]

[0786]

[0787] In the general formula (P-01) to the general formula (P-02), ring A P11 Each independently represents any one of a 1,4-cyclohexylene group in which at least one of -CH2- in the ring may be substituted with -O- or -S-, and a 1,4-phenylene group in which at least one of -CH= in the ring may be substituted with -N=, wherein ring A P11 At least one of the hydrogen atoms in may be substituted with a halogen atom. Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0788] Furthermore, in the presence of multiple rings A P11 In the case of , they may be the same or different.

[0789] In the case of increasing Δn, ring A P11 Preferably, at least one of the -CH= in the ring may be substituted with -N=, and preferably, at least one of the -CH2- in the ring may be substituted with -O- or -S-, and more preferably, the following formula (A P11 -1)~Formula (A P11 -6) Any of the structures represented.

[0790] [Chemistry 112]

[0791]

[0792] L P11 Each independently represents a single bond, -C2H4-, -CH=CH-, -C≡C-, -COO-, -OCO-, -CH2O-, -OCH2-, -CF2O-, or -OCF2-. P11 In the case of , they may be the same or different.

[0793] In general formulas (P-01) to (P-02), m P11 Indicates an integer from 1 to 4.

[0794] In the general formulas (P-01) to (P-02), Y P11 and Y P12 Each independently represents a hydrogen atom or a fluorine atom.

[0795] In the general formulas (P-01) to (P-02), X P11 It represents any one of -F, -Cl, -CN, -NCS, -CF3, -OCF3, an alkyl group having 1 to 6 carbon atoms in which at least one hydrogen atom is substituted by a halogen atom, and an alkoxy group having 1 to 6 carbon atoms in which at least one hydrogen atom is substituted by a halogen atom.

[0796] Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

[0797] As the liquid crystal compound represented by the general formula (P-01), compounds represented by the general formulas (P-01-1) to (P-01-28) are preferred.

[0798] [Chemistry 113]

[0799]

[0800] [Chemistry 114]

[0801]

[0802] [Chemistry 115]

[0803]

[0804] [Chemistry 116]

[0805]

[0806] [Chemistry 117]

[0807]

[0808] In the general formulas (P-01-1) to (P-01-28), R P12 It represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0809] As the compound represented by the general formula (P-02), compounds represented by the general formulas (P-02-1) to (P-02-6) are preferred.

[0810] [Chemistry 118]

[0811]

[0812] In the general formulas (P-02-1) to (P-02-6), R P12 It represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0813] The liquid crystal compounds represented by General Formula (P-01) to General Formula (P-02) may be selected from any one group and used, or may be selected from various groups and used in combination.

[0814] When the reliability of the liquid crystal composition containing the polymerizable compound of the present invention is emphasized, it is preferred to use a liquid crystal compound selected from the group represented by general formula (P-01-1) to general formula (P-01-11), general formula (P-01-16) to general formula (P-01-20) and general formula (P-02-1) to general formula (P-02-4), among which it is more preferred to use a liquid crystal compound selected from the group represented by general formula (P-01-1), general formula (P-01-2), general formula (P-01-4), general formula (P-01-17) and general formula (P-01-20).

[0815] When the low viscosity of the liquid crystal composition containing the polymerizable compound of the present invention is emphasized, it is preferred to use a liquid crystal compound selected from the group represented by general formula (P-01-12) to general formula (P-01-15), general formula (P-01-21) to general formula (P-01-28) and general formula (P-01-5) to general formula (P-01-6), among which it is more preferred to use a liquid crystal compound selected from the group represented by (P-01-12), (P-01-13), (P-01-22), (P-01-23) and (P-01-26).

[0816] When attaching importance to the low viscosity of the liquid crystal composition containing the polymerizable compound of the present invention and further attaching importance to improving the transmittance in the Fringe Field Switching (FFS) mode, it is preferred to use a liquid crystal compound selected from the group represented by general formula (P-01-14), general formula (P-01-15), general formula (P-01-25), general formula (P-01-27) and general formula (P-01-28).

[0817] In order to shorten the UV irradiation process time in the production process of the liquid crystal display element of the present invention, it is preferred to use a liquid crystal compound selected from the group represented by general formula (P-01-4) to general formula (P-01-7), general formula (P-01-20) and general formula (P-01-4), among which liquid crystal compounds selected from (P-01-4) or (P-01-20) are particularly preferred. By using liquid crystal compounds from these groups, deterioration of the liquid crystal composition containing the polymerizable compound during UV irradiation, reduction in the voltage holding ratio of the liquid crystal display element, occurrence of afterimages and other undesirable conditions will not occur, or their degree can be reduced.

[0818] The liquid crystal compounds represented by general formula (P-01) to general formula (P-02), general formula (P-01-1) to general formula (P-01-28) and / or general formula (P-02-1) to general formula (P-02-6) are appropriately selected according to the characteristics required of the liquid crystal display element, and multiple types can be used in combination as needed, but it is preferred to use one or more types, preferably one to twelve types, preferably two to ten types, and preferably three to eight types.

[0819] The preferred lower limit of the total content of liquid crystal compounds represented by general formula (P-01) to general formula (P-02), general formula (P-01-1) to general formula (P-01-28) or general formula (P-02-1) to general formula (P-02-6) in 100 mass% of the liquid crystal composition containing polymerizable compounds is 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, and 80 mass%.

[0820] The preferred upper limit values ​​of the total content of liquid crystal compounds represented by general formula (P-01) to general formula (P-02), general formula (P-01-1) to general formula (P-01-28) or general formula (P-02-1) to general formula (P-02-6) in 100 mass% of the liquid crystal composition containing the polymerizable compound are 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass% and 25 mass%.

[0821] In the liquid crystal composition containing polymerizable compounds of the present invention, the total content of the liquid crystal compounds represented by general formula (P-01) to general formula (P-02), general formula (P-01-1) to general formula (P-01-28) or general formula (P-02-1) to general formula (P-02-6) can be appropriately adjusted according to the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, dielectric constant anisotropy, etc.

[0822] In order to maintain the viscosity of the polymerizable compound-containing liquid crystal composition of the present invention low and to increase the response speed, it is preferred to lower the lower limit and also lower the upper limit.

[0823] When the T of the liquid crystal composition containing the polymerizable compound of the present invention is NI In order to maintain a high temperature and improve the temperature stability, it is preferable to lower the lower limit value and also lower the upper limit value.

[0824] In order to maintain the driving voltage of the polymerizable compound-containing liquid crystal composition of the present invention low and increase the dielectric anisotropy, it is preferable to increase the lower limit and the upper limit.

[0825] The polymerizable compound-containing liquid crystal composition of the present invention may contain, in addition to the liquid crystal compound, common nematic liquid crystals, discotic liquid crystals, cholesteric liquid crystals, and the like.

[0826] The polymerizable compound-containing liquid crystal composition of the present invention may contain additives.

[0827] Examples of the additives include antioxidants, ultraviolet absorbers, light stabilizers, and infrared absorbers.

[0828] As the antioxidant, antioxidants represented by General Formula (H-1) to General Formula (H-4) are preferred.

[0829] [Chemistry 119]

[0830]

[0831] The lower limit of the total content of the antioxidant in 100% by mass of the liquid crystal composition containing the polymerizable compound is preferably 10 mass ppm, preferably 20 mass ppm, preferably 50 mass ppm, and the upper limit is preferably 10,000 mass ppm, preferably 1,000 mass ppm, preferably 500 mass ppm, preferably 100 mass ppm.

[0832] In the general formulas (H-1) to (H-3), R H1 Each independently represents an alkyl group having 3 to 7 carbon atoms.

[0833] More specifically, R in the general formula (H-1) H1 represents an alkyl group having 7 carbon atoms, and R in the general formula (H-2) H1 represents an alkyl group with 3 carbon atoms, and R in the general formula (H-3) H1 It represents an alkyl group having 3 carbon atoms.

[0834] In the general formula (H-4), M H1 It represents an alkylene group having 4 to 10 carbon atoms (one or two or more non-adjacent -CH2- groups in the group may be substituted with -CO-O- or -O-CO- in a manner such that the oxygen atom is not directly adjacent), a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted with a fluorine atom), or a trans-1,4-cyclohexylene group.

[0835] The number of carbon atoms in the alkylene group having 4 to 10 carbon atoms is preferably 4 to 8.

[0836] A polymerization initiator may be added to the liquid crystal composition containing the polymerizable compound of the present invention for the purpose of rapidly promoting polymerization of the polymerizable compound.

[0837] As the polymerization initiator, a photopolymerization initiator is preferably selected.

[0838] Examples of the photopolymerization initiator include acetophenone-based initiators such as diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, 4'-phenoxyacetophenone, and 4'-ethoxyacetophenone; benzoin-based initiators such as benzoin, benzoin isopropyl ether, benzoin isobutyl ether, benzoin methyl ether, and benzoin ethyl ether; acylphosphine oxide-based initiators such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide; and benzyl, Methylphenylglyoxylate series; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, acrylated benzophenone, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 2,5-dimethoxybenzophenone, Benzophenone series such as methyl benzophenone and 3,4-dimethyl benzophenone; thioxanthone series such as 2-isopropyl thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone; aminobenzophenone series such as michler's ketone and 4,4'-diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, camphorquinone, etc.

[0839] The upper limit of the total content of the photopolymerization initiator in the polymerizable compound-containing liquid crystal composition based on 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 100 mass ppm, preferably 56 mass ppm, preferably 48 mass ppm, and preferably 36 mass ppm.

[0840] The dielectric anisotropy of the liquid crystal composition used in the liquid crystal composition containing the polymerizable compound at 25°C may be negative (Δε<-2), neutral (-2≦Δε≦2), or positive (2<Δε), but is preferably negative (Δε<-2).

[0841] The value of dielectric anisotropy (Δε: measured at 25° C.) can be calculated from the formula: Δε=ε∥−ε⊥.

[0842] The dielectric constants (ε∥, ε⊥) were measured as follows.

[0843] A) Determination of dielectric constant (ε∥): A vertical alignment film is applied to a thoroughly cleaned glass substrate and calcined. Two glass substrates are arranged with the alignment film-coated surfaces facing each other. A spacer and a sealant are sandwiched so that the distance between the glass substrates (cell gap) is approximately 10 μm. The sealant is cured to obtain a vertical alignment element. A liquid crystal composition used in a liquid crystal composition containing a polymerizable compound is injected into the vertical alignment element and sealed with an adhesive that cures under ultraviolet light. A sinusoidal wave (0.3 V, 1 kHz) is applied to the vertical alignment element, and the dielectric constant (ε∥) of the liquid crystal composition used in the liquid crystal composition containing a polymerizable compound in the long axis direction is measured.

[0844] B) Determination of dielectric constant (ε⊥): A horizontal alignment film is applied to a thoroughly cleaned glass substrate, calcined, and then rubbed. Two glass substrates are arranged with the alignment film-coated surfaces facing each other and the rubbing direction at 180°. A spacer and a sealant are sandwiched so that the distance between the glass substrates (cell gap) is approximately 10 μm. The sealant is cured to obtain an antiparallel horizontal alignment element. A liquid crystal composition used in a liquid crystal composition containing a polymerizable compound is injected into the antiparallel horizontal alignment element, and the element is sealed with an adhesive that cures under ultraviolet light. A sine wave (20.0 V, 1 kHz) is applied to the antiparallel horizontal alignment element, and the dielectric constant (ε⊥) of the liquid crystal composition used in the liquid crystal composition containing a polymerizable compound in the short axis direction is measured.

[0845] When the dielectric anisotropy of the liquid crystal composition used in the liquid crystal composition containing the polymerizable compound at 25°C is negative (Δε<-2), the dielectric anisotropy (Δε) of the liquid crystal composition at 25°C is preferably less than -2.0 and greater than -4.5, preferably -2.1 to -4.3, preferably -2.3 to -4.0, and preferably -2.5 to -3.9.

[0846] Liquid crystal phase upper limit temperature (nematic phase-isotropic liquid phase transition temperature, T ni ) is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase.

[0847] T ni The measurement is performed by preparing a microscope specimen by sandwiching the liquid crystal composition between a slide glass and a cover glass, and observing the specimen under a polarizing microscope while heating the specimen on a hot stage.

[0848] Alternatively, it can be measured by differential scanning calorimetry (DSC), with "°C" being used as the unit.

[0849] T niThe higher the value, the more the nematic phase can be maintained at high temperatures, thereby expanding the driving temperature range.

[0850] In the case where the dielectric anisotropy of the liquid crystal composition used in the liquid crystal composition containing the polymerizable compound at 25° C. is negative (Δε<-2), the nematic phase-isotropic liquid phase transition temperature (T ni ) is preferably 60℃~120℃, preferably 65℃~110℃, preferably 65℃~95℃.

[0851] Δn (refractive index anisotropy) is determined by the anomalous refractive index (n) of the liquid crystal composition at 25°C using an Abbe refractometer. e ) and the ordinary refractive index (n o ) difference (n e -n o ) to find out.

[0852] When the dielectric constant anisotropy of the liquid crystal composition used in the liquid crystal composition containing the polymerizable compound at 25°C is negative (Δε<-2), the refractive index anisotropy (Δn) of the liquid crystal composition at 25°C is preferably 0.08 to 0.14, preferably 0.09 to 0.13, and preferably 0.09 to 0.12.

[0853] The rotational viscosity (γ1) is the viscosity rate related to the rotation of liquid crystal molecules and can be measured using LCM-2 (manufactured by Toyo Technica) by filling a liquid crystal composition containing a polymerizable compound into a glass cell with a cell gap of about 10 μm.

[0854] The measurement was performed at a temperature of 25°C, and the unit used was mPa·s.

[0855] In the case of a liquid crystal composition having positive dielectric anisotropy, a horizontal alignment unit is used, and in the case of a liquid crystal composition having negative dielectric anisotropy, a vertical alignment unit is used.

[0856] The smaller γ1 is, the faster the response speed of the liquid crystal composition is, and thus the liquid crystal composition is suitable for any liquid crystal display element.

[0857] When the dielectric constant anisotropy of the liquid crystal composition used in the liquid crystal composition containing the polymerizable compound at 25°C is negative (Δε<-2), the rotational viscosity (γ1) of the liquid crystal composition at 25°C is preferably 50mPa·s~160mPa·s, preferably 50mPa·s~160mPa·s, preferably 55mPa·s~140mPa·s, preferably 60mPa·s~120mPa·s, preferably 65mPa·s~110mPa·s, and preferably 70mPa·s~100mPa·s.

[0858] The combination of compounds used in the liquid crystal composition containing a polymerizable compound is preferably: 1) a combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (NU-01) (including subordinate concepts); 2) a combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (NU-05) (including subordinate concepts); 3) a combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (NU-05) (including subordinate concepts); 1) a compound represented by the general formula (N-01) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (N-02) (including subordinate concepts); 2) a compound represented by the general formula (N-03) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (N-04) (including subordinate concepts); 3) a compound represented by the general formula (N-05) (including subordinate concepts), a compound represented by the general formula (N-06) (including subordinate concepts), a sensitizing compound (including subordinate concepts), a compound represented by the general formula (N-07) (including subordinate concepts), and a compound represented by the general formula (N-08) (including subordinate concepts); 4) a compound represented by the general formula (N-01) (including subordinate concepts), a compound represented by the general formula (N-02) (including subordinate concepts), a sensitizing compound (including subordinate concepts), and a compound represented by the general formula (N-04) (including subordinate concepts); 5) a compound represented by the general formula (N-01) (including subordinate concepts), a compound represented by the general formula (N-05) (including subordinate concepts) 6) Combinations of compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), sensitizing compounds (including subordinate concepts), compounds represented by general formula (N-01) (including subordinate concepts), and compounds represented by general formula (N-04) (including subordinate concepts); 7) Combinations of compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), sensitizing compounds (including subordinate concepts), compounds represented by general formula (NU-01) (including subordinate concepts), compounds represented by general formula (NU-05) (including subordinate concepts), A combination of a compound represented by the general formula (N-01) (including subordinate concepts) and a compound represented by the general formula (N-04) (including subordinate concepts); 8) a combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii) (including subordinate concepts), a sensitizing compound (including subordinate concepts), a compound represented by the general formula (NU-01) (including subordinate concepts), a compound represented by the general formula (NU-03) (including subordinate concepts), a compound represented by the general formula (NU-05) (including subordinate concepts), a compound represented by the general formula (N-01) (including subordinate concepts), and a compound represented by the general formula (N-04) (including subordinate concepts);9) Compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), sensitizing compounds (including subordinate concepts), compounds represented by general formula (NU-01) (including subordinate concepts), compounds represented by general formula (NU-02) (including subordinate concepts), compounds represented by general formula (NU-05) (including subordinate concepts), compounds represented by general formula (N-01) (including subordinate concepts), compounds represented by general formula (N-03) (including subordinate concepts), and compounds represented by general formula (N-04) (including subordinate concepts) ) combination; 10) a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii) (including subordinate concepts), a sensitizing compound (including subordinate concepts), a compound represented by the general formula (NU-01) (including subordinate concepts), a compound represented by the general formula (NU-03) (including subordinate concepts), a compound represented by the general formula (NU-05) (including subordinate concepts), a compound represented by the general formula (N-01) (including subordinate concepts), a compound represented by the general formula (N-03) (including subordinate concepts), and a compound represented by the general formula (N-04) ( 11) a combination of compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), sensitizing compounds (including subordinate concepts), compounds represented by general formula (NU-01) (including subordinate concepts), compounds represented by general formula (NU-02) (including subordinate concepts), compounds represented by general formula (NU-03) (including subordinate concepts), compounds represented by general formula (NU-05) (including subordinate concepts), compounds represented by general formula (N-01) (including subordinate concepts), and compounds represented by general formula (N-03) (including subordinate concepts). 12) Combinations of compounds represented by general formula (i) (including sub-concepts), compounds represented by general formula (ii) (including sub-concepts), sensitizing compounds (including sub-concepts), compounds represented by general formula (NU-01) (including sub-concepts), compounds represented by general formula (NU-03) (including sub-concepts), compounds represented by general formula (NU-05) (including sub-concepts), compounds represented by general formula (N-01) (including sub-concepts), and compounds represented by general formula (N-03) (including sub-concepts).

[0859] (Liquid Crystal Display Element)

[0860] Next, a liquid crystal display element is described, namely, a liquid crystal display element comprising two substrates, and a liquid crystal layer comprising a liquid crystal composition containing the polymerizable compound between the two substrates, wherein the liquid crystal composition containing the polymerizable compound contains a polymer formed by polymerizing the polymerizable compound represented by the general formula (i).

[0861] More specifically, it is a liquid crystal display element comprising two substrates and a liquid crystal layer comprising a liquid crystal composition containing a polymerizable compound that has been polymerized and is sandwiched between the two substrates, wherein the liquid crystal composition containing a polymerizable compound that has been polymerized contains a polymer formed by polymerizing the polymerizable compound represented by the general formula (i).

[0862] Furthermore, when the composition containing a polymerizable compound contains a polymerizable liquid crystal compound having a structure different from that of general formula (i), a polymer obtained by polymerizing the polymerizable liquid crystal compound having a structure different from that of general formula (i) may also be present.

[0863] Examples of the polymerization treatment include ultraviolet irradiation.

[0864] The two substrates are divided into a first substrate and a second substrate.

[0865] The first substrate may include a pixel electrode layer having transparent pixel electrodes driven by active elements corresponding to the second substrate and / or an alignment film.

[0866] In addition, it can be constructed as follows: a transparent electrode layer including a transparent common electrode has a plurality of gate buses and data buses arranged in a matrix for each pixel, a thin film transistor arranged at the intersection of the gate bus and the data bus, and an electrode layer of a pixel electrode driven by the thin film transistor.

[0867] In addition, the second substrate may further include a transparent electrode layer including a transparent common electrode, a color filter layer and / or an alignment film layer as needed.

[0868] The liquid crystal display element of the present invention is preferably driven by an active matrix method or a passive matrix method.

[0869] Furthermore, the liquid crystal display element of the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of liquid crystal molecules in the liquid crystal composition.

[0870] In addition, the liquid crystal display element of the present invention may be a PSA type, polymer sustained vertical alignment (PSVA) type, vertical alignment (VA) type, in-plane switching (IPS) type, FFS type, polymer sustained (PS)-IPS type, PS-FFS type, new production skill (NPS) type, or electrically controlled birefringence (ECB) type liquid crystal display element, preferably a PSA type, PSVA type, IPS type, or FFS type liquid crystal display element.

[0871] The VA-type liquid crystal display element may be a general VA-type, a TN-VA-type, or a chiral VA-type having a liquid crystal layer further containing a chiral agent.

[0872] More specifically, the following description will be given using the accompanying drawings.

[0873] Figure 1 This is a schematic diagram showing an example of the liquid crystal display element of the present invention.

[0874] In addition, the structure of the liquid crystal display element of the present invention is not limited to the above-described example.

[0875] In addition, Figure 1 In the figure, for the convenience of explanation, each component is shown separately.

[0876] Figure 1 The liquid crystal display element 1 shown in FIG. 1 includes a first substrate 2 and a second substrate 3 arranged to face each other, and a liquid crystal layer 4 provided between the first substrate 2 and the second substrate 3 .

[0877] like Figure 1 As shown in FIG. 1 , a pixel electrode layer 5 is formed on the surface of the first substrate 2 facing the liquid crystal layer 4 .

[0878] On the second substrate 3 , a transparent electrode layer 6 is formed on the liquid crystal layer 4 side.

[0879] The first substrate 2 and the second substrate 3 may be sandwiched by a pair of polarizing plates (a first polarizing plate 7 and a second polarizing plate 8 ).

[0880] A color filter layer 9 may be further disposed on the liquid crystal layer 4 side of the second substrate 3 .

[0881] The liquid crystal layer 4 contains the liquid crystal composition containing the polymerizable compound of the present invention.

[0882] In the case of a liquid crystal display element manufactured using a liquid crystal composition containing a polymerizable compound, polymers of the polymerizable compound generated by ultraviolet irradiation during the manufacturing process are localized at the interface between the first substrate 2 and the second substrate 3 in the liquid crystal layer 4 .

[0883] That is, in Figure 1 In this case, a polymer of the polymerizable compound is formed at the interface between the liquid crystal layer 4 and the pixel electrode layer 5 and the transparent electrode layer 6 .

[0884] Although not shown in the figure, the liquid crystal display element of the present invention may include a first substrate and a second substrate facing each other, a liquid crystal layer arranged between the first substrate and the second substrate and containing the liquid crystal composition containing the polymerizable compound of the present invention, a first orientation film on the surface of the first substrate on the liquid crystal layer side, and a second orientation film on the surface of the second substrate on the liquid crystal layer side.

[0885] That is, the liquid crystal display element of the present invention can be set as the following structure: a first polarizer, a first substrate, a first alignment film, a pixel electrode layer, a liquid crystal layer, a transparent electrode layer, a color filter layer, a second alignment film, a second substrate, and a second polarizer are stacked in this order.

[0886] The alignment film has a function of aligning liquid crystal molecules.

[0887] As the alignment film, an alignment film commonly used in liquid crystal display elements, such as a polyimide alignment film, can be used.

[0888] The liquid crystal display element of the present invention can be produced by a known method.

[0889] [Example]

[0890] Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not limited to the Examples.

[0891] Hereinafter, in the compositions of Examples and Comparative Examples, the following abbreviations are used to describe the compounds: In addition, "n" represents a natural number.

[0892] Ring structure

[0893] [Chemistry 120]

[0894]

[0895] Sidechain

[0896]

[0897] <Connection base>

[0898] -n- -C n H 2n -

[0899] -nO- -C n H 2n -O-

[0900] -On- -OC n H 2n -

[0901] <Physical Properties of Liquid Crystal Composition Used in Liquid Crystal Composition Containing a Polymerizable Compound>

[0902] The following physical property values ​​were measured for the liquid crystal composition used in the liquid crystal composition containing a polymerizable compound.

[0903] T ni : Nematic-isotropic liquid phase transition temperature (℃)

[0904] Δn: refractive index anisotropy at 25°C

[0905] Δε: Dielectric anisotropy at 25°C

[0906] γ1: Rotational viscosity at 25°C (mPa·s)

[0907] <Polymerizable compound represented by general formula (i) (polymerizable compound a)>

[0908] As the polymerizable compound represented by the general formula (i), the following compounds were used.

[0909] [Chemistry 121]

[0910]

[0911] [Chemistry 122]

[0912]

[0913] <Sensitizing compound (SC)>

[0914] As the sensitizing compound (SC), the following compounds were used.

[0915] [Chemistry 123]

[0916]

[0917] <Polymerizable liquid crystal compound having a structure different from that of general formula (i) (polymerizable compound b)>

[0918] As the polymerizable liquid crystal compound having a structure different from that of the general formula (i), the following compounds were used.

[0919] [Chemistry 124]

[0920]

[0921] <Preparation of Liquid Crystal Composition (Base Composition) Used in Liquid Crystal Composition Containing a Polymerizable Compound>

[0922] As shown in Table 1, liquid crystal compounds were mixed at various ratios to prepare liquid crystal compositions LC-1 to LC-10 used in liquid crystal compositions containing polymerizable compounds, and their physical properties were measured.

[0923] [Table 1]

[0924]

[0925] (Examples 1 to 35 and Comparative Examples 1 to 11)

[0926] <Preparation of Liquid Crystal Composition Containing a Polymerizable Compound>

[0927] To 100 parts by mass of each of the prepared LC-1 to LC-10, polymerizable compound a, polymerizable compound b, and a sensitizing compound (SC) were added in the amounts (parts by mass) listed in Table 2, thereby preparing liquid crystal compositions containing polymerizable compounds of Examples 1 to 35 and Comparative Examples 1 to 11.

[0928] <Production of Liquid Crystal Display Devices>

[0929] A liquid crystal composition containing a polymerizable compound was injected into a liquid crystal cell with a cell gap of 3.5 μm, which was composed of a substrate coated with a polyimide alignment film that caused vertical alignment and subjected to a rubbing treatment and provided with indium tin oxide (ITO). The liquid crystal cell into which the liquid crystal composition containing the polymerizable compound was injected was then irradiated with ultraviolet light for 90 minutes using a fluorescent UV lamp to produce a liquid crystal display element. The fluorescent UV lamp was adjusted to an illuminance of 3.0 mW / cm2, measured at a central wavelength of 313 nm. 2 to use.

[0930] <Evaluation Test>

[0931] The following evaluation tests were performed on each of the polymerizable compound-containing liquid crystal compositions of Examples and Comparative Examples. The results are shown in Tables 2 to 4.

[0932] (Evaluation method of monomer reactivity)

[0933] The liquid crystal composition was extracted from the produced liquid crystal display device, and the total amount of the remaining polymerizable compound a and the polymerizable compound b was quantified by high performance liquid chromatography (HPLC).

[0934] The evaluation criteria are as follows.

[0935] A: less than 50ppm

[0936] B: 50ppm or more and less than 100ppm

[0937] C: 100ppm or more and less than 200ppm

[0938] D: 200ppm or more

[0939] (Evaluation Method of Voltage Holding Ratio)

[0940] The voltage holding ratio (VHR) of the produced liquid crystal display element was measured under the conditions of 1 V, 0.6 Hz, and 60°C.

[0941] The evaluation criteria are as follows.

[0942] A: More than 95%

[0943] B: Less than 95% and 90% or more

[0944] C: less than 90% and 80% or more

[0945] D: less than 80%

[0946] (Evaluation Method for Pretilt Angle Formation)

[0947] First, the pretilt angle of the produced liquid crystal display element was measured and referred to as the pretilt angle (initial). Next, while applying a voltage of 10 V at a frequency of 100 Hz to the liquid crystal display element, ultraviolet light was irradiated for 200 seconds using a fluorescent UV lamp, and the pretilt angle of the liquid crystal display element was measured and referred to as the pretilt angle (after UV).

[0948] Then, the value obtained by subtracting the pretilt angle (after UV) from the measured pretilt angle (initial) was defined as the pretilt angle change [°].

[0949] The pretilt angle was measured using OPTIPRO manufactured by Shintech.

[0950] The fluorescent UV lamp was adjusted to an illuminance of 3.0 mW / cm2 at a central wavelength of 313 nm. 2 to use.

[0951] The evaluation criteria are as follows.

[0952] A: Pretilt angle change is 2.0° or more

[0953] B: Pretilt angle change is less than 2.0° and 1.5° or more

[0954] C: Pretilt angle change is less than 1.5° and 1.0° or more

[0955] D: Pretilt angle change is less than 1.0°

[0956] (Evaluation method for low-temperature storage properties)

[0957] The liquid crystal composition containing the polymerizable compound was filtered using a membrane filter (Agilent Technologies, PTFE 13 mm - 0.2 μm) and 0.5 g was weighed into a test tube. The sample was then degassed under vacuum (2.5 hPa to 2.0 hPa) for 15 minutes, purged with nitrogen, and capped with a rubber stopper to obtain a sample for low-temperature storage evaluation. The sample was stored in a freezer at -20°C and observed daily for precipitation.

[0958] The evaluation criteria are as follows.

[0959] ○: No precipitation was observed even after storage for 10 days.

[0960] △: Precipitation was observed within 6 to 9 days.

[0961] ×: Those precipitated within 5 days are marked as ×.

[0962] [Table 2]

[0963]

[0964] [Table 3]

[0965]

[0966] [Table 4]

[0967]

[0968] From Tables 2 to 4, it can be confirmed that Examples 1 to 35 containing the sensitizing compound (SC) have better monomer reactivity than Comparative Examples 1 to 11 containing no sensitizing compound (SC).

[0969] The liquid crystal compositions of Examples 1 to 30, which contain both polymerizable compounds a and b as shown in Tables 2 and 3, have improved voltage holding ratios and pretilt angle variations compared to the liquid crystal compositions of Comparative Examples 1 to 10, which contain polymerizable compounds b as shown in Table 4 but do not contain polymerizable compounds a and sensitizing compounds (SC), and have the same base composition. They also have good low-temperature storage properties, demonstrating superior performance. Comparing the liquid crystal compositions of Example 1 and Comparative Example 1, which have the same base composition, shows that both voltage holding ratios and pretilt angle variations are improved in Example 1 compared to Comparative Example 1. This is believed to be because the liquid crystal composition of Example 1, as described above, reduces the effects of impurities present in the liquid crystal cell by containing polymerizable compounds a and sensitizing compounds (SC).

[0970] Moreover, by comparing the liquid crystal compositions of Examples 1 to 21 in which the total content of polymerizable compound a and polymerizable compound b is 0.7% by mass, the liquid crystal compositions of Comparative Examples 1 to 10 which do not contain polymerizable compound a and a sensitizing compound (SC) but contain 0.3% by mass of polymerizable compound b, and the liquid crystal composition of Comparative Example 11 which does not contain polymerizable compound a and a sensitizing compound (SC) but contains 0.7% by mass of polymerizable compound b, it can be confirmed that the improvements in voltage holding ratio, pretilt angle change and low-temperature storage properties are not due to the increase in the total content of polymerizable compound a and polymerizable compound b, but are due to the effects brought about by the addition of polymerizable compound a and a sensitizing compound (SC).

[0971] Furthermore, according to Examples 1 to 30, it was confirmed that a liquid crystal composition having more excellent performance can be obtained by using the polymerizable compound a and the polymerizable compound b in addition to the sensitizing compound (SC).

[0972] From the above results, it can be said that in order to achieve all the performances, it is preferable to contain the polymerizable compound a, the polymerizable compound b, and the sensitizing compound SC.

[0973] Based on the above, it can be confirmed that by including one or more polymerizable compounds represented by general formula (i), one or more sensitizing compounds, and one or more liquid crystal compounds, a liquid crystal composition containing a polymerizable compound can be obtained, which can provide a liquid crystal display element with a low residual monomer amount, voltage holding ratio (VHR), formation of a pretilt angle, and good low-temperature storage properties.

[0974] (Example 36 to Example 50)

[0975] Furthermore, as described in Table 5, liquid crystal compounds were mixed at various ratios to prepare liquid crystal compositions LC-11 and LC-12 for use in polymerizable compound-containing liquid crystal compositions, and their physical properties were measured. Then, polymerizable compound a, polymerizable compound b, and a sensitizing compound (SC) were added to 100 parts by mass of each of the prepared LC-11 and LC-12 in the amounts (parts by mass) described in Table 6 to prepare polymerizable compound-containing liquid crystal compositions of Examples 36 to 50. These compositions were evaluated in the same manner as in Examples 1 to 36, confirming the same effects. The results are shown in Tables 5 and 6.

[0976] [Table 5]

[0977] Table 5 LC-11 LC-12 LC-13 3-Cy-Cy-2 6 3-Cy-Cy-V 29.5 29.5 29.5 3-Cy-Ph-01 16 9 3-Ph-Ph-1 3-Ph-Ph-01 5 V2-Ph-Ph-1 8 3-Cy-Ph-Ph-1 8 7 8 3-Cy-Ph-Ph-2 3-Cy-Ph-Ph-02 3 3-Cy-Cy-Ph5-02 4 3-Cy-10-Ph5-01 2 5 7 3-Cy-10-Ph5-02 12 12 3-Cy-Cy-10-Ph5-02 13 V-Cy-Cy-10-Ph5-02 1V-Cy-Cy-10-Ph5-02 6 2-Cy-Ph-Ph5-02 5.5 5 3-Cy-Ph-Ph5-02 13 13.5 6.5 3-Cy-Ph-Ph5-04 13 1-Ph-2-Ph-Ph5-02 10 10 2-Ph-2-Ph-Ph5-02 3-Ph-2-Ph-Ph5-02 4 Total (mass) % 100 100 100 <![CDATA[T ni [℃]]]> 70.1 74.0 74.7 Δn 0.1092 0.1166 0.1065 Δε -2.80 -2.82 -2.57 <![CDATA[γ1[mPa·s]]]> 76 82 72

[0978] [Table 6]

[0979]

[0980] [Industrial Applicability]

[0981] The liquid crystal composition containing the polymerizable compound of the present invention can be used in a liquid crystal display device.

Claims

1. A liquid crystal composition containing a polymerizable compound, comprising at least: One or more polymerizable compounds represented by the following formulas (i-1), (i-3), and (i-4); further containing one or more polymerizable compounds represented by formula (ii-1) or formula (ii-3) different from those of formula (i-1), (i-3), or (i-4); One or more compounds represented by general formula (SC); and One or more liquid crystal compounds, Where, P i1 and P i2 Each independently represents a polymerizable group, Sp i1 and Sp i2 represents a single bond or an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkylene group may be independently substituted by halogen atoms. Oxygen atoms do not bond directly to each other. Substituent Sr i1 represents any one of a halogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. Oxygen atoms do not bond directly to each other. In the presence of multiple substituents Sr i1 In the case of , they may be the same or different, Sp i1 、Sp i2 and / or substituent Sr i1 at least one of represents an alkylene group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, In Sp i1 、Sp i2 and / or substituent Sr i1 At least one of the alkylene groups having 1 to 20 carbon atoms or the alkyl groups having 1 to 20 carbon atoms represented by One or more -CH2-, and / or One or more hydrogen atoms in the group are independently selected from the following formula (PG i -1)~Formula(PG i -33) is substituted by a group consisting of a group represented by Equation (PG i -1) to Equation (PG i -33), X PGi and Z PGi each independently represents a methylene group, an oxygen atom or a sulfur atom, Y PGi represents a carbonyl group, a sulfinyl group, an oxygen atom or a sulfur atom, W PGi represents a methylene, carbonyl or sulfinyl group, S PGi 、T PGi and U PGi Each independently represents a methine or a nitrogen atom, In the formula (PG i -18), S PGi and T PGi Not simultaneously representing methine, In the formula (PG i -19), S PGi 、T PGi and U PGi Not simultaneously representing methine, R PGi each independently represents an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. Oxygen atoms do not bond directly to each other. In the presence of multiple R PGi In the case of , they may be the same or different, Sp PGi each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms, One or more -CH2- in the alkylene group or the arylene group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkylene group or the arylene group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkylene group or the arylene group may be independently substituted by a halogen atom or a hydroxyl group. Oxygen atoms do not bond directly to each other. In the presence of multiple Sp PGi In the case of , they may be the same or different, * indicates a bonding bond, in, One or more -CH2- in the group is selected from the formula (PG i -1)~Formula(PG i -7) is substituted by a group consisting of a group represented by One or more hydrogen atoms in the group are selected from the formula (PG i -8)~Formula(PG i -33) is substituted by a group consisting of a group represented by; In the formula, Spii1 and Spii2 each independently represent a polymerizable group; Rii6 and Rii7 each independently represent an alkyl group having 1 to 18 carbon atoms or a halogen atom; In formula (SC), R SC1 and R SC2 each independently represents an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. Oxygen atoms do not bond directly to each other. S SC2 、S SC3 、S SC5 and S SC6 each independently represents a hydrogen atom or a fluorine atom, A SC1 Each independently represents a group selected from the group consisting of the following groups (a) and (b): (a) 1,4-cyclohexylene, wherein one -CH2- or two or more non-adjacent -CH2- groups present in the group may be substituted with -O- and / or -S-; (b) 1,4-phenylene, wherein one -CH= or two or more non-adjacent -CH= present in the group may be substituted with -N=, The A SC1 One or more hydrogen atoms in the can be substituted independently by Sr SC1 replace, Substituent Sr SC1 represents any one of a halogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O- or -NH-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -CO-O- or -O-CO-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. Oxygen atoms do not bond directly to each other. In the presence of multiple substituents Sr SC1 In the case of , they may be the same or different, n SC1 Indicates an integer from 0 to 1; The liquid crystal compound includes a compound selected from the group consisting of compounds represented by any one of the following general formulas (NU-01) to (NU-08), In the general formulas (NU-01) to (NU-08), R NU1 and R NU2 Each independently represents any one of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, One or more -CH2-CH2- in the group may be independently replaced by -C≡C-, -CO-, -CO-O- or -O-CO-. Oxygen atoms are not directly bonded to each other.

2. The liquid crystal composition containing a polymerizable compound according to claim 1, wherein The formula (PG i -1) is substituted with a group represented by 3. The liquid crystal composition containing a polymerizable compound according to claim 1 or 2, wherein The Sp i2 It represents an alkylene group having 1 to 20 carbon atoms.

4. The liquid crystal composition containing a polymerizable compound according to claim 1 or 2, wherein The n i1 is 0.

5. The liquid crystal composition containing a polymerizable compound according to claim 1 or 2, wherein The L i1 For a single bond.

6. The liquid crystal composition containing a polymerizable compound according to claim 1 or 2, wherein The divalent aromatic group represents any one of 1,4-phenylene, naphthalene-2,6-diyl, anthracene-2,6-diyl, phenanthrene-2,7-diyl, indan-2,5-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl. The divalent cyclic aliphatic group represents any one of 1,4-cyclohexylene, 1,4-cyclohexenylene, and 1,3-dioxane-2,5-diyl. The divalent heterocyclic compound group represents either a pyridine-2,5-diyl group or a pyrimidine-2,5-diyl group.

7. A liquid crystal display element comprising two substrates, and A liquid crystal layer is included between the two substrates, wherein the liquid crystal layer comprises the liquid crystal composition containing a polymerizable compound according to claim 1 or 2, The liquid crystal display element comprises the liquid crystal composition containing the polymerizable compound according to claim 1 or 2.

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