Liquid crystal composition containing pigment compound and element using the same

Abstract

The object of the present invention is to provide a liquid crystal composition containing a pigment compound with excellent solubility and retention and good light resistance, and an element using the same. By using one or more of a predetermined alkenyl compound and a compound having a predetermined difluorinated structure in combination, a liquid crystal composition containing a pigment compound with excellent solubility and retention and good light resistance can be obtained, and the liquid crystal composition containing the pigment compound is effectively used in an element, particularly a dimming element.

Description

Technical Field

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

[0002] Liquid crystal materials are not only used in various display elements for displaying text, images, and videos, such as televisions (TV) and smartphones, but are also being put to practical use as dimming elements for adjusting the transmittance of light.

[0003] Among them, when a "guest-host (GH) type liquid crystal composition" is used in which a pigment compound is added to a host liquid crystal composition, a polarizing plate is not required, so a light-adjusting element with high transmittance can be obtained at low cost, and thus it is highly anticipated.

[0004] Research on GH-type liquid crystal compositions has been conducted since ancient times, and attempts have been made to develop liquid crystal display elements or dimming elements having specified properties (for example, high contrast, high solubility of liquid crystal compositions and pigment compounds, excellent light resistance, and excellent heat resistance) (Patent Documents 1 to 4).

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: International Publication No. 2017 / 038616

[0008] Patent Document 2: Japanese Patent Application Publication No. 2019-85581

[0009] Patent Document 3: International Publication No. 2018 / 078968

[0010] Patent Document 4: Japanese Patent Publication No. 2017-513975 Summary of the invention

[0011] Problems to be solved by the invention

[0012] However, higher performance (high contrast, high solubility of the liquid crystal composition and the pigment compound, excellent light resistance, excellent heat resistance, etc.) is required in liquid crystal compositions containing pigment compounds, and the inventions described in Patent Documents 1 to 4 have room for further improvement.

[0013] An object of the present invention is to provide a liquid crystal composition containing a pigment compound, which has excellent solubility of the pigment compound and retention of the solubility of the pigment compound and good light resistance, and a device using the same.

[0014] Technical means of solving problems

[0015] The present inventors have found that the above-mentioned problems can be solved by using one or two or more of a predetermined alkenyl compound and a compound having a predetermined difluoro structure in combination, thereby completing the present invention.

[0016] The structure of the present invention for solving the above-mentioned problems is as follows.

[0017] The liquid crystal composition containing a pigment compound of the present invention is characterized by comprising:

[0018] One or more compounds represented by the following general formula (i);

[0019] One or more compounds represented by the following general formula (ii); and

[0020] One or more pigment compounds,

[0021] [Chemistry 1]

[0022]

[0023] (In general formula (i),

[0024] R i1 represents an alkenyl group having 2 to 20 carbon atoms,

[0025] One or more -CH 2 - may be independently substituted by -O- and / or -CO-,

[0026] One or more -CH 2 -CH 2 - may be independently substituted by -CH=CH- and / or -C≡C-,

[0027] One or more hydrogen atoms in the alkenyl group may be independently substituted by halogen atoms.

[0028] Oxygen atoms do not bond directly to each other.

[0029] R i2 represents an alkyl group having 1 to 20 carbon atoms,

[0030] One or more -CH 2 - may be independently substituted by -O- and / or -CO-,

[0031] One or more -CH 2 -CH 2 - may be independently substituted by -CH=CH- and / or -C≡C-,

[0032] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0033] Oxygen atoms do not bond directly to each other.

[0034] A i1 represents a group (a) and a group (b) selected from the following:

[0035] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0036] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0037] The basis of the group is

[0038] The A i1 One or more hydrogen atoms in the group may be independently replaced by halogen atoms.

[0039] L i2 , L i3 , L i4 , L i5 Each independently represents a hydrogen atom or a halogen atom. )

[0040] [Chemistry 2]

[0041]

[0042] (In general formula (ii),

[0043] R ii1 represents an alkyl group having 1 to 20 carbon atoms,

[0044] One or more -CH 2 - may be independently substituted by -O- and / or -CO-,

[0045] One or more -CH 2 -CH 2 - may be independently substituted by -CH=CH- and / or -C≡C-,

[0046] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0047] Oxygen atoms do not bond directly to each other.

[0048] A ii1 and A ii2Each independently represents a group (a) and a group (b) selected from the following:

[0049] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0050] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0051] The basis of the group is

[0052] The A ii1 and A ii2 One or more hydrogen atoms in the may be independently replaced by halogen atoms. ).

[0053] Furthermore, the element of the present invention is characterized by using the liquid crystal composition containing the pigment compound.

[0054] Effects of the Invention

[0055] According to the present invention, by using in combination one or more of the specified alkenyl compounds and a compound having a specified difluoro structure, a liquid crystal composition containing a pigment compound having excellent solubility and good light resistance can be obtained, and the liquid crystal composition containing the pigment compound is effectively used in elements, especially dimming elements.

[0056] More specifically, the liquid crystal composition containing a pigment compound of the present invention can prevent the pigment compound from precipitating even at a low temperature of -25°C and can be used in a wide temperature range.

[0057] Furthermore, it is excellent in light resistance and can suppress changes in color tone.

[0058] Therefore, the present invention can be applied to automotive applications, portable terminal applications such as smartphones and tablet computers, and light control device applications such as window glass, etc., where adaptability to harsh environments is important. DETAILED DESCRIPTION

[0059] (Compound represented by general formula (i))

[0060] The pigment compound-containing liquid crystal composition of the present invention contains one or two or more alkenyl compounds represented by the following general formula (i).

[0061] [Chemistry 3]

[0062]

[0063] In the general formula (i), Ri1 It represents an alkenyl group having 2 to 20 carbon atoms.

[0064] The alkenyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0065] The alkenyl group having 2 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0066] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0067] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0068] In addition, one or two or more hydrogen atoms in the alkenyl group may be independently substituted with a halogen atom.

[0069] Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom.

[0070] However, when the alkenyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0071] For example, R i1 By replacing one of the alkenyl groups with a -CH 2 - is substituted with -O- and can represent an alkenyloxy group having 2 to 19 carbon atoms.

[0072] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0073] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0074] As R i1 Specific examples of alkenyl groups having 2 to 20 carbon atoms (including substituted alkenyl groups) include the following: i1 -1)~Formula (R i1 -10) represented by the base, etc.

[0075] [Chemistry 4]

[0076]

[0077] Formula (R i1 -1)~Formula (R i1 -10), the black dots represent the bonds to the ring structure.

[0078] In addition, as Ri1 From the viewpoint of improving the solubility of the dye compound, a linear alkenyl group having 2 to 6 carbon atoms is preferred.

[0079] In the general formula (i), R i2 It represents an alkyl group having 1 to 20 carbon atoms.

[0080] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0081] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0082] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0083] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0084] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0085] Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom.

[0086] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0087] For example, R i2 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0088] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0089] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0090] In addition, R i2 By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0091] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0092] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0093] In addition, R i2 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0094] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0095] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0096] In addition, R i2 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0097] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0098] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0099] In addition, R i2 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0100] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0101] The number of carbon atoms in the halogenated alkyl group is preferably 2-10, and more preferably 2-6.

[0102] As R i2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: i2 -1)~Formula (R i2 -31) represented by the base, etc.

[0103] [Chemistry 5]

[0104]

[0105] Formula (R i2 -1)~Formula (R i2 -31), the black dots represent the bonds to the ring structure.

[0106] In addition, as R i2 From the viewpoint of high solubility and lowering the viscosity of the liquid crystal composition containing the pigment compound, a linear alkyl group having 1 to 6 carbon atoms is preferred.

[0107] In the general formula (i), A i1 represents a group (a) and a group (b) selected from the following:

[0108] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0109] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0110] The basis of the group.

[0111] In addition, A i1 One or two or more hydrogen atoms in the may be independently substituted by halogen atoms.

[0112] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0113] More specifically, A i1 Preferably, it is represented by the following formula (A i1 -1)~Formula (A i1 -2) any one of.

[0114] [Chemistry 6]

[0115]

[0116] Formula (A i1 -1)~Formula (A i1 -2), the white dots represent the bonds to the 1,4-cyclohexylene group, and the black dots represent the bonds to the 1,4-phenylene group.

[0117] In the general formula (i), L i2 , L i3 , L i4 , L i5 Each independently represents a hydrogen atom or a halogen atom.

[0118] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0119] From the viewpoint of high light resistance of the liquid crystal composition containing the pigment compound, L i2 , L i3 , Li4 , L i5 All are preferably hydrogen atoms.

[0120] As the compound represented by the general formula (i), compounds represented by the following general formulas (i-1) to (i-2) are preferred.

[0121] [Chemistry 7]

[0122]

[0123] In the general formula (i-1) to the general formula (i-2), R i1 and R i2 represents the same as R in the general formula (i) i1 and R i2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0124] As the compound represented by the general formula (i-1), compounds represented by the following structural formulas (i-1.1) to (i-1.8) are preferred.

[0125] [Chemistry 8]

[0126]

[0127] As the compound represented by the general formula (i-2), compounds represented by the following structural formulas (i-2.1) and (i-2.2) are preferred.

[0128] [Chemistry 9]

[0129]

[0130] The types of compounds represented by general formula (i), general formula (i-1) to general formula (i-2), structural formula (i-1.1) to structural formula (i-1.8) or structural formula (i-2.1) to structural formula (i-2.2) used in the liquid crystal composition containing pigment compounds are one or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two, and preferably one.

[0131] The lower limit of the total content of the compounds represented by general formula (i), general formula (i-1) to general formula (i-2), structural formula (i-1.1) to structural formula (i-1.8) or structural formula (i-2.1) to structural formula (i-2.2) in 100 mass % of a liquid crystal composition containing pigment compounds is preferably 1 mass % or more, preferably 5 mass % or more, and preferably 10 mass % or more.

[0132] The upper limit value of the total content of compounds represented by general formula (i), general formula (i-1) to general formula (i-2), structural formula (i-1.1) to structural formula (i-1.8) or structural formula (i-2.1) to structural formula (i-2.2) in 100 mass % of a liquid crystal composition containing pigment compounds is preferably 35 mass % or less, preferably 30 mass % or less, and preferably 25 mass % or less.

[0133] The total content of the compounds represented by general formula (i), general formula (i-1) to general formula (i-2), structural formula (i-1.1) to structural formula (i-1.8) or structural formula (i-2.1) to structural formula (i-2.2) in 100 mass % of the liquid crystal composition containing the pigment compound is preferably 1 mass % to 35 mass %, preferably 5 mass % to 30 mass %, and preferably 10 mass % to 25 mass %.

[0134] The compounds represented by the general formula (i), general formula (i-1) to general formula (i-2), structural formula (i-1.1) to structural formula (i-1.8) or structural formula (i-2.1) to structural formula (i-2.2) can be synthesized using a known synthesis method.

[0135] (Compound represented by general formula (ii))

[0136] The pigment compound-containing liquid crystal composition of the present invention contains one or two or more compounds having a difluorinated structure represented by the following general formula (ii).

[0137] [Chemistry 10]

[0138]

[0139] In the general formula (ii), R ii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0140] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0141] 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.

[0142] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0143] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0144] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0145] Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom.

[0146] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0147] For example, R ii1 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0148] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0149] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0150] In addition, R ii1 By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0151] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0152] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0153] In addition, R ii1 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0154] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0155] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0156] In addition, R ii1 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0157] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0158] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0159] In addition, R ii1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0160] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0161] The number of carbon atoms in the halogenated alkyl group is preferably 2-10, and more preferably 2-6.

[0162] As R ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: ii1 -1)~Formula (R ii1 -31) represented by the base, etc.

[0163] [Chemistry 11]

[0164]

[0165] Formula (R ii1 -1)~Formula (R ii1 -31), the black dots represent the bonds to the ring structure.

[0166] In addition, as R ii1 From the viewpoint of high solubility and lowering the viscosity of the liquid crystal composition containing the pigment compound, a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 1 to 6 carbon atoms is preferred.

[0167] In the general formula (ii), A ii1 and A ii2 Each independently represents a group (a) and a group (b) selected from the following:

[0168] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0169] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0170] The basis of the group.

[0171] In addition, A ii1 and A ii2One or two or more hydrogen atoms in the may be independently substituted by halogen atoms.

[0172] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0173] More specifically, A ii1 and A ii2 Preferably, it is represented by the following formula (A ii1 / 2 -1)~Formula (A ii1 / 2 -2) any one of.

[0174] [Chemistry 12]

[0175]

[0176] Formula (A ii1 / 2 -1)~Formula (A ii1 / 2 -2), the white dot indicates the direction to R ii1 or A ii1 The black dots indicate the bond to A ii2 or a (3F)-1,4-phenylene bond.

[0177] As the compound represented by the general formula (ii), compounds represented by the following general formulas (ii-1) to (ii-3) are preferred.

[0178] [Chemistry 13]

[0179]

[0180] In the general formulas (ii-1) to (ii-3), R ii1 represents the same as R in the general formula (ii) ii1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0181] As the compound represented by the general formula (ii-1), compounds represented by the following structural formulas (ii-1.1) to (ii-1.4) are preferred.

[0182] [Chemistry 14]

[0183]

[0184] As the compound represented by the general formula (ii-2), compounds represented by the following structural formulas (ii-2.1) to (ii-2.4) are preferred.

[0185] [Chemistry 15]

[0186]

[0187] As the compound represented by the general formula (ii-3), compounds represented by the following structural formulas (ii-3.1) to (ii-3.4) are preferred.

[0188] [Chemistry 16]

[0189]

[0190] The types of 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-2.4) or structural formula (ii-3.1) to structural formula (ii-3.4) used in the liquid crystal composition containing pigment compounds are one or more, preferably one to five, preferably one to four, preferably one to three, and preferably one to two.

[0191] The lower limit value of the total content of the 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-2.4) or structural formula (ii-3.1) to structural formula (ii-3.4) in 100 mass % of a liquid crystal composition containing pigment compounds is preferably 1 mass % or more, preferably 5 mass % or more, and preferably 10 mass % or more.

[0192] The upper limit value of the total content of the 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-2.4) or structural formula (ii-3.1) to structural formula (ii-3.4) in 100 mass % of a liquid crystal composition containing pigment compounds is preferably 30 mass % or less, preferably 25 mass % or less, and preferably 20 mass % or less.

[0193] The total content of the 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-2.4) or structural formula (ii-3.1) to structural formula (ii-3.4) in 100 mass% of the liquid crystal composition containing the pigment compound is preferably 1 mass% to 30 mass%, preferably 5 mass% to 25 mass%, and preferably 10 mass% to 20 mass%.

[0194] The 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-2.4) or structural formula (ii-3.1) to structural formula (ii-3.4) can be synthesized using known synthesis methods.

[0195] (Other compounds)

[0196] (Compound represented by general formula (iii))

[0197] From the viewpoint of further increasing the dielectric anisotropy of the pigment compound-containing liquid crystal composition, the pigment compound-containing liquid crystal composition of the present invention may further contain one or more compounds having a trifluoro structure represented by the following general formula (iii).

[0198] [Chemistry 17]

[0199]

[0200] In the general formula (iii), R iii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0201] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0202] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0203] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0204] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[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 and a bromine atom.

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

[0208] For example, R iii1 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0209] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0210] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0211] In addition, R iii1 By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0212] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0213] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0214] In addition, R iii1 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0215] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0216] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0217] In addition, R iii1 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0218] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0219] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0220] In addition, R iii1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0221] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0222] The number of carbon atoms in the halogenated alkyl group is preferably 2-10, and more preferably 2-6.

[0223] As R iii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: iii1 -1)~Formula (R iii1 -31) represented by the base, etc.

[0224] [Chemistry 18]

[0225]

[0226] Formula (R iii1 -1)~Formula (R iii1 -31), the black dots represent the bonds to the ring structure.

[0227] In addition, as R iii1 From the viewpoint of high solubility and lowering the viscosity of the liquid crystal composition containing the pigment compound, a linear alkyl group having 1 to 6 carbon atoms is preferred.

[0228] In the general formula (iii), A iii1 and A iii2 Each independently represents a group (a) and a group (b) selected from the following:

[0229] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0230] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0231] The basis of the group.

[0232] In addition, A iii1 and A iii2 One or two or more hydrogen atoms in the may be independently substituted by halogen atoms.

[0233] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0234] As A iii1 and A iii2 The substitution position of the halogen atom in the formula (A iii1 / 2 -SP-1).

[0235] [Chemistry 19]

[0236]

[0237] Formula (A iii1 / 2 -SP-1), S iii1 / 2 Each independently represents a halogen atom, and a white dot represents a iii1 or A iii1 The black dots indicate the bond to A iii2 or a bond of (3F,5F)-1,4-phenylene.

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

[0239] More specifically, A iii1 and A iii2 Preferably, it is represented by the following formula (A iii1 / 2 -1)~Formula (A iii1 / 2 -3) any one of.

[0240] [Chemistry 20]

[0241]

[0242] Formula (A iii1 / 2 -1)~Formula (A iii1 / 2 -3), the white dot indicates the direction to R iii1 or A iii1 The black dots indicate the bond to A iii2 or a bond of (3F,5F)-1,4-phenylene.

[0243] As the compound represented by the general formula (iii), compounds represented by the following general formulas (iii-1) to (iii-5) are preferred.

[0244] [Chemistry 21]

[0245]

[0246] In the general formulae (iii-1) to (iii-5), R iii1 represents the same as R in the general formula (iii) iii1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0247] In the general formula (iii-1) to the general formula (iii-5), S iii1 / 2 Each independently represents a halogen atom.

[0248] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0249] The compound represented by the general formula (iii-1) is preferably a compound represented by the following structural formula (iii-1.1).

[0250] [Chemistry 22]

[0251]

[0252] The compound represented by the general formula (iii-2) is preferably a compound represented by the following structural formula (iii-2.1).

[0253] [Chemistry 23]

[0254]

[0255] The compound represented by the general formula (iii-3) is preferably a compound represented by the following structural formula (iii-3.1).

[0256] [Chemistry 24]

[0257]

[0258] The compound represented by the general formula (iii-4) is preferably a compound represented by the following structural formula (iii-4.1).

[0259] [Chemistry 25]

[0260]

[0261] The compound represented by the general formula (iii-5) is preferably a compound represented by the following structural formula (iii-5.1).

[0262] [Chemistry 26]

[0263]

[0264] The types of compounds represented by general formula (iii), general formula (iii-1) to general formula (iii-5), structural formula (iii-1.1), structural formula (iii-2.1), structural formula (iii-3.1), structural formula (iii-4.1) or structural formula (iii-5.1) used in the liquid crystal composition containing pigment compounds are one or more, preferably one to five, preferably one to four, preferably one to three, and preferably one to two.

[0265] The lower limit of the total content of the compounds represented by general formula (iii), general formula (iii-1) to general formula (iii-5), structural formula (iii-1.1), structural formula (iii-2.1), structural formula (iii-3.1), structural formula (iii-4.1) or structural formula (iii-5.1) in 100 mass % of a liquid crystal composition containing pigment compounds is preferably 1 mass % or more, preferably 5 mass % or more, and preferably 10 mass % or more.

[0266] The upper limit value of the total content of compounds represented by general formula (iii), general formula (iii-1) to general formula (iii-5), structural formula (iii-1.1), structural formula (iii-2.1), structural formula (iii-3.1), structural formula (iii-4.1) or structural formula (iii-5.1) in 100 mass% of a liquid crystal composition containing pigment compounds is preferably 35 mass% or less, preferably 30 mass% or less, and preferably 25 mass% or less.

[0267] The total content of the compounds represented by general formula (iii), general formula (iii-1) to general formula (iii-5), structural formula (iii-1.1), structural formula (iii-2.1), structural formula (iii-3.1), structural formula (iii-4.1) or structural formula (iii-5.1) in 100 mass% of the liquid crystal composition containing the pigment compound is preferably 1 mass% to 35 mass%, preferably 5 mass% to 30 mass%, and preferably 10 mass% to 25 mass%.

[0268] Compounds represented by general formula (iii), general formula (iii-1) to general formula (iii-5), structural formula (iii-1.1), structural formula (iii-2.1), structural formula (iii-3.1), structural formula (iii-4.1) or structural formula (iii-5.1) can be synthesized using known synthesis methods.

[0269] (Compound represented by general formula (iv))

[0270] From the viewpoint of reducing the viscosity of the pigment compound-containing liquid crystal composition, the pigment compound-containing liquid crystal composition of the present invention may further contain one or more compounds represented by the following general formula (iv) having a cyclohexane ring and a benzene ring.

[0271] [Chemistry 27]

[0272]

[0273] In the general formula (iv), R iv1 and R iv2 Each independently represents an alkyl group having 1 to 20 carbon atoms.

[0274] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0275] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0276] One or more -CH 2- may be substituted independently by -O- and / or -CO-.

[0277] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0278] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0279] Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom.

[0280] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0281] For example, R iv1 and R iv2 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0282] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0283] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0284] In addition, R iv1 and R iv2 By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0285] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0286] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0287] In addition, R iv1 and R iv2 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0288] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0289] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0290] In addition, R iv1 and R iv2 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0291] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0292] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0293] In addition, R iv1 and R iv2 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0294] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0295] The number of carbon atoms in the halogenated alkyl group is preferably 2-10, and more preferably 2-6.

[0296] As R iv1 and R iv2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: iv1 / 2 -1)~Formula (R iv1 / 2 -31) represented by the base, etc.

[0297] [Chemistry 28]

[0298]

[0299] Formula (R iv1 / 2 -1)~Formula (R iv1 / 2 -31), the black dots represent the bonds to the ring structure.

[0300] In addition, as R iv1 From the viewpoint of reducing the viscosity of the liquid crystal composition containing the pigment compound, a linear alkyl group having 1 to 6 carbon atoms or a linear alkoxy group having 1 to 6 carbon atoms is preferred.

[0301] In addition, as R iv2 From the viewpoint of increasing the refractive index anisotropy of the liquid crystal composition containing the pigment compound, a linear alkoxy group having 1 to 6 carbon atoms is preferred.

[0302] As the compound represented by the general formula (iv), compounds represented by the following structural formulas (iv-1.1) to (iv-1.5) are preferred.

[0303] [Chemistry 29]

[0304]

[0305] The types of compounds represented by general formula (iv) or structural formula (iv-1.1) to structural formula (iv-1.5) used in the liquid crystal composition containing pigment compounds are one or more, preferably one to five, preferably one to four, preferably one to three, and preferably one to two.

[0306] The lower limit of the total content of the compounds represented by general formula (iv) or structural formula (iv-1.1) to structural formula (iv-1.5) in 100 mass % of the liquid crystal composition containing the pigment compound is preferably 1 mass % or more, preferably 3 mass % or more, and preferably 5 mass % or more.

[0307] The upper limit of the total content of the compounds represented by general formula (iv) or structural formula (iv-1.1) to structural formula (iv-1.5) in 100 mass % of the liquid crystal composition containing the pigment compound is preferably 45 mass % or less, preferably 40 mass % or less, and preferably 35 mass % or less.

[0308] The total content of the compounds represented by general formula (iv) or structural formula (iv-1.1) to structural formula (iv-1.5) in 100 mass % of the liquid crystal composition containing the pigment compound is preferably 1 mass % to 45 mass %, preferably 3 mass % to 40 mass %, and preferably 5 mass % to 35 mass %.

[0309] The compounds represented by the general formula (iv) or structural formulas (iv-1.1) to (iv-1.5) can be synthesized using a known synthesis method.

[0310] (Compound represented by general formula (v))

[0311] From the perspective of driving liquid crystals at an appropriate voltage, the liquid crystal composition containing a pigment compound of the present invention may also include a liquid crystal compound having a positive dielectric anisotropy (2≦Δε) at 25°C, or one or more compounds represented by the following general formula (v), which are so-called P-type compounds.

[0312] The dielectric anisotropy (Δε) of the liquid crystal compound is a value extrapolated from a measured value of the dielectric anisotropy of a composition obtained by adding the liquid crystal compound to a composition having substantially neutral dielectric properties at 25°C.

[0313] [Chemistry 30]

[0314]

[0315] In the general formula (v), R v1 Each independently represents an alkyl group having 1 to 20 carbon atoms.

[0316] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0317] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0318] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0319] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0320] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.

[0321] Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom.

[0322] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0323] For example, R v1 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0324] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0325] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0326] In addition, R v1 By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0327] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0328] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0329] In addition, R v1 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0330] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0331] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0332] In addition, R v1 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0333] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0334] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0335] In addition, R v1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0336] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0337] The number of carbon atoms in the halogenated alkyl group is preferably 2-10, and more preferably 2-6.

[0338] As R v1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: v1 -1)~Formula (R v1 -31) represented by the base, etc.

[0339] [Chemistry 31]

[0340]

[0341] Formula (R v1 -1)~Formula (R v1 -31), the black dots represent the bonds to the ring structure.

[0342] In addition, as R v1From the viewpoint of reducing the viscosity of the liquid crystal composition containing the pigment compound, a linear alkyl group having 1 to 6 carbon atoms is preferred.

[0343] In the general formula (v), R v2 represents any one of a halogen atom, -CN, -OCN or -C≡CCN.

[0344] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. v2 From the viewpoint of high light resistance or high solubility of a liquid crystal composition containing a pigment compound, a fluorine atom or -CN is preferred.

[0345] In the general formula (v), A v1 and A v2 Each independently represents a group (a), a group (b) and a group (c) selected from the following:

[0346] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0347] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0348] (c) naphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl may be substituted with -N=.)

[0349] The basis of the group.

[0350] In addition, A v1 and A v2 One or two or more hydrogen atoms in the may be independently substituted by halogen atoms.

[0351] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0352] As A v1 and A v2 The substitution position of the halogen atom in the formula (A v1 / 2 -SP-1)~Formula (A v1 / 2 -SP-2).

[0353] [Chemistry 32]

[0354]

[0355] Formula (A v1 / 2-SP-1)~Formula (A v1 / 2 -SP-2), S v1 / 2 Each independently represents a halogen atom, and a white dot represents a v1 or Z v1 The black dots represent the bonds to Z v1 or R v2 The bond key.

[0356] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0357] More specifically, A v1 and A v2 Preferably, it is represented by the following formula (A v1 / 2 -1)~Formula (A v1 / 2 -5) any one of.

[0358] [Chemistry 33]

[0359]

[0360] Formula (A v1 / 2 -1)~Formula (A v1 / 2 -5), the white dot indicates the direction to R v1 or Z v1 The black dots represent the bonds to Z v1 or R v2 The bond key.

[0361] In the general formula (v), Z v1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0362] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0363] The number of carbon atoms in the alkylene group is preferably 2-10, and more preferably 2-6.

[0364] One or more -CH 2 - can be independently -O-, -CH(CH 3 )-, -CO- and / or -CF 2 -replace.

[0365] In addition, one or more -CH 2 -CH 2 - can be independently -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -CH=C(CH 3 )-、-C(CH 3)=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C-.

[0366] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0367] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: v1 -1)~Formula(Z v1 -24) represented by the base, etc.

[0368] [Chemistry 34]

[0369]

[0370] Formula (Z v1 -1)~Formula(Z v1 -24), the white dot indicates the direction to A v1 or A v2 The black dots indicate the bond to A v2 The bond key.

[0371] In addition, as Z vi1 From the viewpoint of high light resistance of a liquid crystal composition containing a pigment compound, a single bond, -CO-O-, -O-CO-, or a linear alkylene group having 1 to 6 carbon atoms is preferred.

[0372] n v1 Indicates an integer from 1 to 3.

[0373] In the presence of multiple A v2 and Z v1 In the case of , these may be the same or different.

[0374] However, among the compounds represented by the general formula (v), the compounds represented by the general formula (ii) and the general formula (iii) (including subordinate concepts) are excluded.

[0375] As the compound represented by the general formula (v), compounds represented by the following general formulas (v-1) to (v-3) are preferred.

[0376] [Chemistry 35]

[0377] R v1 -A v1 -Z v1 -A v2 -R v2 (v-1)

[0378] R v1 -A v1 -Z v1 -Av2 -Z v1-2 -A v2-2 -R v2 (v-2)

[0379] R v1 -A v1 -z v1 -A v2 -Z v1-2 -A v2-2 -z v1-3 -A v2-3 -R v2 (v-3)

[0380] In the general formulas (v-1) to (v-3), R v1 , R v2 , Z v1 , A v1 and A v2 represents the same as R in the general formula (v) v1 , R v2 , Z v1 , A v1 and A v2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0381] In the general formulas (v-1) to (v-3), Z v1-2 and Z v1-3 Each independently represents Z in the general formula (v) v1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0382] In the general formulas (v-1) to (v-3), A v2-2 and A v2-3 Each independently represents the same as A in the general formula (v) v1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0383] As the compound represented by the general formula (v-1), compounds represented by the following general formulas (v-1-1) to (v-1-10) are preferred.

[0384] [Chemistry 36]

[0385]

[0386] In the general formulas (v-1-1) to (v-1-10), R v1 , R v2 represents the same as R in the general formula (v) v1 , R v2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0387] In the general formulas (v-1-1) to (v-1-10), S v1 / 2 Each independently represents a halogen atom.

[0388] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0389] As the compound represented by the general formula (v-1-1), compounds represented by the following structural formulas (v-1-1.1) to (v-1-1.4) are preferred.

[0390] [Chemistry 37]

[0391]

[0392] The compound represented by the general formula (v-1-2) is preferably a compound represented by the following structural formula (v-1-2.1).

[0393] [Chemistry 38]

[0394]

[0395] As the compound represented by the general formula (v-1-3), compounds represented by the following structural formulas (v-1-3.1) to (v-1-3.4) are preferred.

[0396] [Chemistry 39]

[0397]

[0398] As the compound represented by the general formula (v-1-4), compounds represented by the following structural formulas (v-1-4.1) to (v-1-4.2) are preferred.

[0399] [Chemistry 40]

[0400]

[0401] The compound represented by the general formula (v-1-5) is preferably a compound represented by the following structural formula (v-1-5.1).

[0402] [Chemistry 41]

[0403]

[0404] As the compound represented by the general formula (v-1-6), compounds represented by the following structural formulas (v-1-6.1) to (v-1-6.2) are preferred.

[0405] [Chemistry 42]

[0406]

[0407] The compound represented by the general formula (v-1-7) is preferably a compound represented by the following structural formula (v-1-7.1).

[0408] [Chemistry 43]

[0409]

[0410] The compound represented by the general formula (v-1-8) is preferably a compound represented by the following structural formula (v-1-8.1).

[0411] [Chemistry 44]

[0412]

[0413] The compound represented by the general formula (v-1-9) is preferably a compound represented by the following structural formula (v-1-9.1).

[0414] [Chemistry 45]

[0415]

[0416] The compound represented by the general formula (v-1-10) is preferably a compound represented by the following structural formula (v-1-10.1).

[0417] [Chemistry 46]

[0418]

[0419] As the compound represented by the general formula (v-2), compounds represented by the following general formulas (v-2-1) to (v-2-5) are preferred.

[0420] [Chemistry 47]

[0421]

[0422] In the general formulas (v-2-1) to (v-2-5), R v1 , R v2 represents the same as R in the general formula (v) v1 , R v2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0423] In the general formulas (v-2-1) to (v-2-5), S v1 / 2 Each independently represents a halogen atom.

[0424] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0425] The compound represented by the general formula (v-2-1) is preferably a compound represented by the following structural formula (v-2-1.1).

[0426] [Chemistry 48]

[0427]

[0428] As the compound represented by the general formula (v-2-2), compounds represented by the following structural formulas (v-2-2.1) to (v-2-2.2) are preferred.

[0429] [Chemistry 49]

[0430]

[0431] The compound represented by the general formula (v-2-3) is preferably a compound represented by the following structural formula (v-2-3.1).

[0432] [Chemistry 50]

[0433]

[0434] As the compound represented by the general formula (v-2-4), compounds represented by the following structural formulas (v-2-4.1) to (v-2-4.2) are preferred.

[0435] [Chemistry 51]

[0436]

[0437] The compound represented by the general formula (v-2-5) is preferably a compound represented by the following structural formula (v-2-5.1).

[0438] [Chemistry 52]

[0439]

[0440] As the compound represented by the general formula (v-3), compounds represented by the following general formulas (v-3-1) to (v-3-2) are preferred.

[0441] [Chemistry 53]

[0442]

[0443] In the general formula (v-3-1) to the general formula (v-3-2), R v1 , R v2 represents the same as R in the general formula (v) v1 , R v2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0444] In the general formula (v-3-1) to the general formula (v-3-2), S v1 / 2 Each independently represents a halogen atom.

[0445] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0446] As the compound represented by the general formula (v-3-1), compounds represented by the following structural formulas (v-3-1.1) to (v-3-1.2) are preferred.

[0447] [Chemistry 54]

[0448]

[0449] As the compound represented by the general formula (v-3-1), compounds represented by the following structural formulas (v-3-2.1) to (v-3-2.2) are preferred.

[0450] [Chemistry 55]

[0451]

[0452] General formula (v), general formula (v-1) to general formula (v-3), general formula (v-1-1) to general formula (v-1-10), general formula (v-2-1) to general formula (v-2-5), general formula (v-3-1) to general formula (v-3-2), structural formula (v-1-1.1) to structural formula (v-1-1.4), structural formula (v-1-2.1), structural formula (v-1-3.1) to structural formula (v-1-3.4), structural formula (v-1-4.1) to structural formula (v-1-4.2), structural formula (v-1-5.1), structural formula (v-1-6.1) to structural formula (v-1-6.2), structural formula (v-1-7.1), structural formula (v-1-8.1), The compounds represented by structural formula (v-1-9.1), structural formula (v-1-10.1), structural formula (v-2-1.1), structural formula (v-2-2.1) to structural formula (v-2-2.2), structural formula (v-2-3.1), structural formula (v-2-4.1) to structural formula (v-2-4.2), structural formula (v-2-5.1), structural formula (v-3-1.1) to structural formula (v-3-1.2), and structural formula (v-3-2.1) to structural formula (v-3-2.2) are used in the liquid crystal composition containing pigment compounds. One or more types are preferably one to six types, preferably one to five types, preferably one to four types, and preferably one to three types.

[0453] General formula (v), general formula (v-1) to general formula (v-3), general formula (v-1-1) to general formula (v-1-10), general formula (v-2-1) to general formula (v-2-5), general formula (v-3-1) to general formula (v-3-2), structural formula (v-1-1.1) to structural formula (v-1-1.4), structural formula (v-1-2.1), structural formula (v-1-3.1) to structural formula (v-1-3.4), structural formula (v-1-4.1) to structural formula (v-1-4.2), structural formula (v-1-5.1), structural formula (v-1-6.1) to structural formula (v-1-6.2), structural formula (v-1-7.1), structural formula (v-1-8.1 ), structural formula (v-1-9.1), structural formula (v-1-10.1), structural formula (v-2-1.1), structural formula (v-2-2.1) to structural formula (v-2-2.2), structural formula (v-2-3.1), structural formula (v-2-4.1) to structural formula (v-2-4.2), structural formula (v-2-5.1), structural formula (v-3-1.1) to structural formula (v-3-1.2), structural formula (v-3-2.1) to structural formula (v-3-2.2) in 100 mass% of the liquid crystal composition containing the pigment compound, the lower limit of the total content is preferably 1 mass% or more, preferably 3 mass% or more, and preferably 5 mass% or more.

[0454] General formula (v), general formula (v-1) to general formula (v-3), general formula (v-1-1) to general formula (v-1-10), general formula (v-2-1) to general formula (v-2-5), general formula (v-3-1) to general formula (v-3-2), structural formula (v-1-1.1) to structural formula (v-1-1.4), structural formula (v-1-2.1), structural formula (v-1-3.1) to structural formula (v-1-3.4), structural formula (v-1-4.1) to structural formula (v-1-4.2), structural formula (v-1-5.1), structural formula (v-1-6.1) to structural formula (v-1-6.2), structural formula (v-1-7.1), structural formula (v-1-8.1) , structural formula (v-1-9.1), structural formula (v-1-10.1), structural formula (v-2-1.1), structural formula (v-2-2.1) to structural formula (v-2-2.2), structural formula (v-2-3.1), structural formula (v-2-4.1) to structural formula (v-2-4.2), structural formula (v-2-5.1), structural formula (v-3-1.1) to structural formula (v-3-1.2), and structural formula (v-3-2.1) to structural formula (v-3-2.2) in 100 mass% of the liquid crystal composition containing the pigment compound, the upper limit value of the total content is preferably 50 mass% or less, preferably 45 mass% or less, and preferably 40 mass% or less.

[0455] General formula (v), general formula (v-1) to general formula (v-3), general formula (v-1-1) to general formula (v-1-10), general formula (v-2-1) to general formula (v-2-5), general formula (v-3-1) to general formula (v-3-2), structural formula (v-1-1.1) to structural formula (v-1-1.4), structural formula (v-1-2.1), structural formula (v-1-3.1) to structural formula (v-1-3.4), structural formula (v-1-4.1) to structural formula (v-1-4.2), structural formula (v-1-5.1), structural formula (v-1-6.1) to structural formula (v-1-6.2), structural formula (v-1-7.1), structural formula (v-1-8.1), structural formula The total content of the compounds represented by formula (v-1-9.1), structural formula (v-1-10.1), structural formula (v-2-1.1), structural formula (v-2-2.1) to structural formula (v-2-2.2), structural formula (v-2-3.1), structural formula (v-2-4.1) to structural formula (v-2-4.2), structural formula (v-2-5.1), structural formula (v-3-1.1) to structural formula (v-3-1.2), and structural formula (v-3-2.1) to structural formula (v-3-2.2) in 100 mass% of the liquid crystal composition containing the pigment compound is preferably 1 mass% to 50 mass%, preferably 3 mass% to 45 mass%, and preferably 5 mass% to 40 mass%.

[0456] General formula (v), general formula (v-1) to general formula (v-3), general formula (v-1-1) to general formula (v-1-10), general formula (v-2-1) to general formula (v-2-4), general formula (v-3-1) to general formula (v-3-2), structural formula (v-1-1.1) to structural formula (v-1-1.4), structural formula (v-1-2.1), structural formula (v-1-3.1) to structural formula (v-1-3.4), structural formula (v-1-4.1) to structural formula (v-1-4.2), structural formula (v-1-5.1), structural formula (v-1-6.1) to structural formula (v-1- The compounds represented by formula (v-6.2), formula (v-1-7.1), formula (v-1-8.1), formula (v-1-9.1), formula (v-1-10.1), formula (v-2-1.1), formula (v-2-2.1) to formula (v-2-2.2), formula (v-2-3.1), formula (v-2-4.1) to formula (v-2-4.2), formula (v-3-1.1) to formula (v-3-1.2), and formula (v-3-2.1) to formula (v-3-2.2) can be synthesized using known synthesis methods.

[0457] (Compound represented by general formula (vi))

[0458] From the viewpoint of improving the solubility and light resistance of liquid crystal compositions containing pigment compounds, the liquid crystal composition of the present invention may also contain a liquid crystal compound having a neutral dielectric anisotropy (-2<Δε<2) at 25°C, or one or more compounds represented by the following general formula (vi), which are so-called np-type compounds.

[0459] The dielectric anisotropy (Δε) of the liquid crystal compound is a value extrapolated from a measured value of the dielectric anisotropy of a composition obtained by adding the liquid crystal compound to a composition having substantially neutral dielectric properties at 25°C.

[0460] [Chemistry 56]

[0461]

[0462] In the general formula (vi), R vi1 and R vi2 Each independently represents an alkyl group having 1 to 20 carbon atoms.

[0463] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0464] 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.

[0465] One or more -CH 2 - may be substituted independently by -O- and / or -CO-.

[0466] In addition, one or more -CH 2 -CH 2 - may be substituted independently by -CH=CH- and / or -C≡C-.

[0467] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0468] For example, R vi1 and R vi2 By replacing one of the alkyl groups with -CH 2 - is substituted with -O- and may represent an alkoxy group having 1 to 19 carbon atoms.

[0469] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0470] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0471] In addition, R vi1 and R vi2By adding one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyl group having 1 to 20 carbon atoms.

[0472] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0473] The number of carbon atoms in the alkenyl group is preferably 2-10, and more preferably 2-6.

[0474] In addition, R vi1 and R vi2 By adding one or more -CH 2 -CH 2 - is substituted with -C≡C-, and may represent an alkynyl group having 1 to 20 carbon atoms.

[0475] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0476] The number of carbon atoms in the alkynyl group is preferably 2-10, more preferably 2-6.

[0477] In addition, R vi1 and R vi2 By replacing one of the alkyl groups with -CH 2 - is replaced by -O-, and one or more -CH 2 -CH 2 - is substituted with -CH=CH-, which may represent an alkenyloxy group having 1 to 19 carbon atoms.

[0478] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0479] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0480] As R vi1 and R vi2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: vi1 / 2 -1)~Formula (R vi1 / 2 -26) represented by the base, etc.

[0481] [Chemistry 57]

[0482]

[0483] Formula (R vi1 / 2 -1)~Formula (R vi1 / 2 -26), the black dots represent the bonds to the ring structure.

[0484] In addition, as R vi1 and R vi2 From the viewpoint of improving the solubility of the liquid crystal composition containing the pigment compound and improving the light resistance, a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 2 to 6 carbon atoms is preferred.

[0485] In the general formula (vi), A vi1 and A vi2 Each independently represents a group (a), a group (b) and a group (c) selected from the following:

[0486] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S-. )

[0487] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=.)

[0488] (c) naphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl may be substituted with -N=.)

[0489] The basis of the group.

[0490] In addition, A vi1 and A vi2 One or two or more hydrogen atoms in the group may be independently substituted by an alkyl group having 1 to 6 carbon atoms.

[0491] The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, an ethyl group or an n-propyl group.

[0492] As A vi1 and A vi2 The substitution position of the alkyl group having 1 to 6 carbon atoms is preferably the following formula (A vi1 / 2 -SP-1).

[0493] [Chemistry 58]

[0494]

[0495] Formula (A vi1 / 2 -SP-1), S vi1 / 2 represents an alkyl group with 1 to 6 carbon atoms, and a white dot represents an alkyl group with 1 to 6 carbon atoms. vi1 or Z vi1 The black dots represent the bonds to Z vi1 or R vi2 The bond key.

[0496] The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, an ethyl group or an n-propyl group.

[0497] More specifically, A vi1 and A vi2 Preferably, it is represented by the following formula (A vi1 / 2 -1)~Formula (A vi1 / 2 -3) any one of.

[0498] [Chemistry 59]

[0499]

[0500] Formula (A vi1 / 2 -1)~Formula (A vi1 / 2 -3), the white dot indicates the direction to R vi1 or Z vi1 The black dots represent the bonds to Z vi1 or R vi2 The bond key.

[0501] In the general formula (vi), Z vi1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0502] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0503] The number of carbon atoms in the alkylene group is preferably 2-10, and more preferably 2-6.

[0504] One or more -CH 2 - can be independently -O-, -CH(CH 3 )-, -CO- and / or -CF 2 -replace.

[0505] In addition, one or more -CH 2 -CH 2 - can be independently -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -CH=C(CH 3 )-、-C(CH 3 )=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C-.

[0506] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0507] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: vi1-1)~Formula(Z vi1 -24) represented by the base, etc.

[0508] [Chemistry 60]

[0509]

[0510] Formula (Z vi1 -1)~Formula(Z vi1 -24), the white dot indicates the direction to A vi1 or A vi2 The black dots indicate the bond to A vi2 The bond key.

[0511] In addition, as Z vi1 From the viewpoint of improving the solubility of the liquid crystal composition containing the pigment compound and improving the light resistance, a single bond, -CO-O-, or -O-CO- is preferred.

[0512] n vi1 Indicates an integer from 1 to 3.

[0513] In the presence of multiple A vi2 and Z vi1 In the case of , these may be the same or different.

[0514] However, among the compounds represented by general formula (vi), compounds represented by general formula (i) and general formula (iv) (including subordinate concepts) are excluded.

[0515] As the compound represented by the general formula (vi), compounds represented by the following general formulas (vi-1) to (vi-3) are preferred.

[0516] [Chemistry 61]

[0517] R vi1 -A vi1 -Z vi1 -A vi2 -R vi2 (vi-1)

[0518] R vi1 -A vi1 -Z vi1 -A vi2 -Z vi1-2 -A vi2-2 -R vi2 (vi-2)

[0519] R vi1 -A vi1 -Z vi1 -A vi2 -Z vi1-2 -A vi2-2 -Zvi1-3 -A vi2-3 -R vi2 (vi-3)

[0520] In the general formulas (vi-1) to (vi-3), R vi1 , R vi2 , Z vi1 , A vi1 and A vi2 represents the same as R in the general formula (vi) vi1 , R vi2 , Z vi1 , A vi1 and A vi2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0521] In the general formulas (vi-1) to (vi-3), Z vi1-2 and Z vi1-3 Each independently represents Z in the general formula (vi) vi1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0522] In the general formulas (vi-1) to (vi-3), A vi2-2 and A vi2-3 Each independently represents the same as A in the general formula (vi) vi1 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0523] As the compound represented by the general formula (vi-1), compounds represented by the following general formulas (vi-1-1) to (vi-1-4) are preferred.

[0524] [Chemistry 62]

[0525]

[0526] In the general formulas (vi-1-1) to (vi-1-4), R vi1 , R vi2 represents the same as R in the general formula (v) vi1 , R vi2 In the general formula (vi-1-1) to the general formula (vi-1-4), S vi1 / 2 It represents an alkyl group having 1 to 6 carbon atoms.

[0527] The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, an ethyl group or an n-propyl group.

[0528] As the compound represented by the general formula (vi-1-1), compounds represented by the following structural formulas (vi-1-1.1) to (vi-1-1.8) are preferred.

[0529] [Chemistry 63]

[0530]

[0531] As the compound represented by the general formula (vi-1-2), compounds represented by the following structural formulas (vi-1-2.1) to (vi-1-2.5) are preferred.

[0532] [Chemistry 64]

[0533]

[0534] As the compound represented by the general formula (vi-1-3), a compound represented by the following structural formula (vi-1-3.1) is preferred.

[0535] [Chemistry 65]

[0536]

[0537] As the compound represented by the general formula (vi-1-4), compounds represented by the following structural formulas (vi-1-4.1) to (vi-1-4.2) are preferred.

[0538] [Chemistry 66]

[0539]

[0540] As the compound represented by the general formula (vi-2), compounds represented by the following general formulas (vi-2-1) to (vi-2-8) are preferred.

[0541] [Chemistry 67]

[0542]

[0543] In the general formulas (vi-2-1) to (vi-2-8), R vi1 , R vi2 represents the same as R in the general formula (vi) vi1 , R vi2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0544] In the general formula (vi-2-1) to the general formula (vi-2-8), S vi1 / 2 It represents an alkyl group having 1 to 6 carbon atoms.

[0545] The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, an ethyl group or an n-propyl group.

[0546] As the compound represented by the general formula (vi-2-1), compounds represented by the following structural formulas (vi-2-1.1) to (vi-2-1.4) are preferred.

[0547] [Chemistry 68]

[0548]

[0549] As the compound represented by the general formula (vi-2-2), compounds represented by the following structural formulas (vi-2-2.1) to (vi-2-2.5) are preferred.

[0550] [Chemistry 69]

[0551]

[0552] As the compound represented by the general formula (vi-2-3), compounds represented by the following structural formulas (vi-2-3.1) to (vi-2-3.3) are preferred.

[0553] [Chemistry 70]

[0554]

[0555] As the compound represented by the general formula (vi-2-4), compounds represented by the following structural formulas (vi-2-4.1) to (vi-2-4.2) are preferred.

[0556] [Chemistry 71]

[0557]

[0558] As the compound represented by the general formula (vi-2-5), a compound represented by the following structural formula (vi-2-5.1) is preferred.

[0559] [Chemistry 72]

[0560]

[0561] As the compound represented by the general formula (vi-2-6), a compound represented by the following structural formula (vi-2-6.1) is preferred.

[0562] [Chemistry 73]

[0563]

[0564] As the compound represented by the general formula (vi-2-7), a compound represented by the following structural formula (vi-2-7.1) is preferred.

[0565] [Chemistry 74]

[0566]

[0567] As the compound represented by the general formula (vi-2-8), compounds represented by the following structural formulas (vi-2-8.1) to (vi-2-8.5) are preferred.

[0568] [Chemistry 75]

[0569]

[0570] As the compound represented by the general formula (vi-3), compounds represented by the following general formulas (vi-3-1) to (vi-3-2) are preferred.

[0571] [Chemistry 76]

[0572]

[0573] In the general formula (vi-3-1) to the general formula (vi-3-2), R vi1 , R vi2 represents the same as R in the general formula (v) vi1 , R vi2 The above two groups have the same meanings, and the preferred groups also represent the same groups.

[0574] As the compound represented by the general formula (vi-3-1), compounds represented by the following structural formulas (vi-3-1.1) to (vi-3-1.3) are preferred.

[0575] [Chemistry 77]

[0576]

[0577] As the compound represented by the general formula (vi-3-2), compounds represented by the following structural formulas (vi-3-2.1) to (vi-3-2.2) are preferred.

[0578] [Chemistry 78]

[0579]

[0580] General formula (vi), general formula (vi-1) to general formula (vi-3), general formula (vi-1-1) to general formula (vi-1-4), general formula (vi-2-1) to general formula (vi-2-8), general formula (vi-3-1) to general formula (vi-3-2), structural formula (vi-1-1.1) to structural formula (vi-1-1.8), structural formula (vi-1-2.1) to structural formula (vi-1-2.5), structural formula (vi-1-3.1), structural formula (vi-1-4.1) to structural formula (vi-1-4.2), structural formula (vi-2-1.1) to structural formula (vi-2-1.4), structural formula (vi-2-2.1) to structural formula (vi-2-2.5), The types of compounds represented by structural formula (vi-2-3.1) to structural formula (vi-2-3.3), structural formula (vi-2-4.1) to structural formula (vi-2-4.2), structural formula (vi-2-5.1), structural formula (vi-2-6.1), structural formula (vi-2-7.1), structural formula (vi-2-8.1) to structural formula (vi-2-8.2), structural formula (vi-3-1.1) to structural formula (vi-3-1.3), and structural formula (vi-3-2.1) to structural formula (vi-3-2.2) used in the liquid crystal composition are one or more, preferably one to five, preferably one to four, preferably one to three, and preferably one to two.

[0581] General formula (vi), general formula (vi-1) to general formula (vi-3), general formula (vi-1-1) to general formula (vi-1-4), general formula (vi-2-1) to general formula (vi-2-8), general formula (vi-3-1) to general formula (vi-3-2), structural formula (vi-1-1.1) to structural formula (vi-1-1.8), structural formula (vi-1-2.1) to structural formula (vi-1-2.5), structural formula (vi-1-3.1), structural formula (vi-1-4.1) to structural formula (vi-1-4.2), structural formula (vi-2-1.1) to structural formula (vi-2-1.4), structural formula (vi-2-2.1) to structural formula (vi-2-2. 5), the lower limit of the total content of the compounds represented by structural formula (vi-2-3.1) to structural formula (vi-2-3.3), structural formula (vi-2-4.1) to structural formula (vi-2-4.2), structural formula (vi-2-5.1), structural formula (vi-2-6.1), structural formula (vi-2-7.1), structural formula (vi-2-8.1) to structural formula (vi-2-8.2), structural formula (vi-3-1.1) to structural formula (vi-3-1.3), and structural formula (vi-3-2.1) to structural formula (vi-3-2.2) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 3 mass% or more, and preferably 5 mass% or more.

[0582] General formula (vi), general formula (vi-1) to general formula (vi-3), general formula (vi-1-1) to general formula (vi-1-4), general formula (vi-2-1) to general formula (vi-2-8), general formula (vi-3-1) to general formula (vi-3-2), structural formula (vi-1-1.1) to structural formula (vi-1-1.8), structural formula (vi-1-2.1) to structural formula (vi-1-2.5), structural formula (vi-1-3.1), structural formula (vi-1-4.1) to structural formula (vi-1-4.2), structural formula (vi-2-1.1) to structural formula (vi-2-1.4), structural formula (vi-2-2.1) to structural formula (vi-2-2.5) , structural formula (vi-2-3.1) to structural formula (vi-2-3.3), structural formula (vi-2-4.1) to structural formula (vi-2-4.2), structural formula (vi-2-5.1), structural formula (vi-2-6.1), structural formula (vi-2-7.1), structural formula (vi-2-8.1) to structural formula (vi-2-8.2), structural formula (vi-3-1.1) to structural formula (vi-3-1.3), and structural formula (vi-3-2.1) to structural formula (vi-3-2.2) in 100 mass% of the liquid crystal composition has an upper limit value of the total content of 50 mass% or less, preferably 45 mass% or less, and preferably 40 mass% or less.

[0583] General formula (vi), general formula (vi-1) to general formula (vi-3), general formula (vi-1-1) to general formula (vi-1-4), general formula (vi-2-1) to general formula (vi-2-8), general formula (vi-3-1) to general formula (vi-3-2), structural formula (vi-1-1.1) to structural formula (vi-1-1.8), structural formula (vi-1-2.1) to structural formula (vi-1-2.5), structural formula (vi-1-3.1), structural formula (vi-1-4.1) to structural formula (vi-1-4.2), structural formula (vi-2-1.1) to structural formula (vi-2-1.4), structural formula (vi-2-2.1) to structural formula (vi-2-2.5), structural formula The total content of the compounds represented by structural formula (vi-2-3.1) to structural formula (vi-2-3.3), structural formula (vi-2-4.1) to structural formula (vi-2-4.2), structural formula (vi-2-5.1), structural formula (vi-2-6.1), structural formula (vi-2-7.1), structural formula (vi-2-8.1) to structural formula (vi-2-8.2), structural formula (vi-3-1.1) to structural formula (vi-3-1.3), and structural formula (vi-3-2.1) to structural formula (vi-3-2.2) in 100 mass% of the liquid crystal composition is preferably 1 mass% to 50 mass%, preferably 3 mass% to 45 mass%, and preferably 5 mass% to 40 mass%.

[0584] General formula (vi), general formula (vi-1) to general formula (vi-3), general formula (vi-1-1) to general formula (vi-1-4), general formula (vi-2-1) to general formula (vi-2-8), general formula (vi-3-1) to general formula (vi-3-2), structural formula (vi-1-1.1) to structural formula (vi-1-1.8), structural formula (vi-1-2.1) to structural formula (vi-1-2.5), structural formula (vi-1-3.1), structural formula (vi-1-4.1) to structural formula (vi-1-4.2), structural formula (vi-2-1.1) to structural formula (vi-2-1.4), structural formula (vi-1-1.1) to structural formula (vi-2-1.4), structural formula (vi-1-1.8) to structural formula (vi-1-1.5) The compounds represented by structural formula (vi-2-2.1) to structural formula (vi-2-2.5), structural formula (vi-2-3.1) to structural formula (vi-2-3.3), structural formula (vi-2-4.1) to structural formula (vi-2-4.2), structural formula (vi-2-5.1), structural formula (vi-2-6.1), structural formula (vi-2-7.1), structural formula (vi-2-8.1) to structural formula (vi-2-8.2), structural formula (vi-3-1.1) to structural formula (vi-3-1.3), and structural formula (vi-3-2.1) to structural formula (vi-3-2.2) can be synthesized using known synthesis methods.

[0585] (pigment compound)

[0586] The liquid crystal composition of the present invention contains one or two or more kinds of pigment compounds.

[0587] It is preferred that the pigment compound has a maximum absorption between 350 nm and 700 nm, more preferably between 400 nm and 650 nm.

[0588] The method for measuring the maximum absorption wavelength is as follows.

[0589] First, 1.0 part by mass of a dye compound is added to 100 parts by mass of an arbitrary liquid crystal composition in which the dye compound can be dissolved, and the mixture is dissolved to prepare a sample.

[0590] Next, two 2 cm×2 cm glass substrates having indium tin oxide (ITO) electrodes and an orientation film for horizontal orientation on the ITO electrodes were used to prepare a cell including an injection port with the ITO electrode layer as the inner side of the cell and the cell thickness adjusted to 10 μm by plastic particles.

[0591] A sample is injected into the cell, and the injection port is blocked with a sealing material, thereby manufacturing a device.

[0592] Next, the absorption spectrum between 350 nm and 750 nm was measured using the prepared element at 25° C. and without voltage application using a spectrometer (“LCD-5200” manufactured by Otsuka Electronics Co., Ltd.), thereby determining the maximum absorption wavelength of the dye compound.

[0593] When a plurality of dye compounds are used, it is preferred that the plurality of dye compounds have absorption wavelengths different from each other, thereby being able to form a desired color such as black.

[0594] Furthermore, the dye compound is preferably a dichroic dye.

[0595] The pigment compound is preferably selected from the group consisting of azo compounds, anthraquinone compounds, methine compounds, azomethine compounds, merocyanine compounds, quinone compounds, naphthoquinone compounds, tetrazine compounds, perylene compounds, terrylene compounds, quaterrylene compounds, highrylene compounds, indigo compounds, dioxazine compounds, azulene compounds, pyrromethene compounds, spiropyran compounds and diarylethene compounds.

[0596] Examples of the azo compound include disazo compounds and trisazo compounds.

[0597] Specific examples of pigment compounds include SI-486 (yellow, dichroic pigment, azo compound), SI-426 (red, dichroic pigment, azo compound), G-472 (blue, dichroic pigment, azo compound), M-483 (dichroic pigment, blue), and M-412 (dichroic pigment, blue).

[0598] The pigment compound is used in a pigment compound-containing liquid crystal composition in one or more types, preferably one to five types, preferably one to four types, and preferably one to three types.

[0599] The lower limit of the total content of the pigment compounds in 100% by mass of the liquid crystal composition containing the pigment compounds is preferably 0.1% by mass or more, preferably 0.5% by mass or more, and preferably 1% by mass or more.

[0600] The upper limit of the total content of the pigment compounds in 100% by mass of the liquid crystal composition containing the pigment compounds is preferably 20% by mass or less, preferably 15% by mass or less, and preferably 10% by mass or less.

[0601] The total content of the pigment compound in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 0.1% by mass to 20% by mass, preferably 0.5% by mass to 15% by mass, and preferably 1% by mass to 10% by mass.

[0602] The lower limit of the amount of the pigment compound added relative to 100 parts by mass of the liquid crystal composition containing no pigment compound and no additive is preferably 0.1 parts by mass or more, preferably 0.5 parts by mass or more, and preferably 1 part by mass or more.

[0603] The upper limit of the amount of the pigment compound added relative to 100 parts by mass of the liquid crystal composition containing no pigment compound and additives is preferably 20 parts by mass or less, preferably 15 parts by mass or less, and preferably 10 parts by mass or less.

[0604] The amount of the pigment compound added is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and more preferably 1 to 10 parts by mass based on 100 parts by mass of the liquid crystal composition containing no pigment compound and additives.

[0605] (Liquid crystal composition containing pigment compound)

[0606] The pigment compound-containing liquid crystal composition of the present invention can be produced by mixing, for example, the compounds represented by the general formulae (i) to (ii), the pigment compound, the other compounds as required, and additives.

[0607] More specifically, it can be manufactured by the following steps, namely, a step of obtaining a liquid crystal composition for a liquid crystal composition containing a pigment compound by mixing the compounds represented by the general formula (i) to the general formula (ii) and the other compounds as needed; and a step of obtaining a liquid crystal composition containing a pigment compound by mixing a pigment compound and an optional additive in a liquid crystal composition for the liquid crystal composition containing a pigment compound.

[0608] Alternatively, the pigment compound-containing liquid crystal composition can be produced by mixing a liquid crystal compound, a pigment compound, and optional additives constituting the liquid crystal composition used in the pigment compound-containing liquid crystal composition in any order to obtain the pigment compound-containing liquid crystal composition.

[0609] Examples of the additive include stabilizers, chiral agents, antistatic agents, nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, and polymerizable compounds.

[0610] Examples of the stabilizer include antioxidants, ultraviolet (UV) absorbers, light stabilizers, and infrared absorbers.

[0611] Examples of the antioxidant include hydroquinone derivatives, nitrosamine-based polymerization inhibitors, and hindered phenol-based antioxidants.

[0612] More specifically, tert-butylhydroquinone, methylhydroquinone, "Q-1300" and "Q-1301" manufactured by Wako Pure Chemical Industries, Ltd., and "IRGANOX 1010", "IRGANOX 1035", "IRGANOX 1076", "IRGANOX 1098", "IRGANOX 1135", and "IRGANOX 1136" manufactured by BASF. 1330", "IRGANOX 1425", "IRGANOX 1520", "IRGANOX 1726", "IRGANOX 245", "IRGANOX 259", "IRGANOX 3114", "IRGANOX 3790", "IRGANOX 5057", "IRGANOX 565", etc.

[0613] The ultraviolet (UV) absorber is preferably an ultraviolet (UV) absorber that absorbs less visible light with a wavelength of 400 nm or more from the viewpoint of excellent absorption of ultraviolet light with a wavelength of 370 nm or less and good liquid crystal display properties.

[0614] More specifically, for example, hindered phenol compounds, benzotriazole compounds, hydroxybenzophenone compounds, salicylate compounds, benzophenone compounds, cyanoacrylate compounds, nickel complex salt compounds, triazine compounds, and the like are mentioned.

[0615] Examples of the hindered phenol-based compound include 2,6-di-tert-butyl-p-cresol, pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamic acid amide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, and tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate.

[0616] Examples of the benzotriazole compounds include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2,2-methylenebis(4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol), 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine, triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis[1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di-(1,2-di- (3,5-di-tert-butyl-4-hydroxy-hydrocinnamic acid), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5-di-tert-amylphenyl)-5-chlorobenzotriazole, 2,6-di-tert-butyl-p-cresol, pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].

[0617] More specifically, there can be mentioned “TINUVIN 109”, “TINUVIN 171”, “TINUVIN 326”, “TINUVIN 327”, “TINUVIN 328”, “TINUVIN 770”, “TINUVIN 900”, “TINUVIN 928” manufactured by BASF Corporation of Japan, and “KEMISORB 71”, “KEMISORB 73”, and “KEMISORB 74” manufactured by Chemipro Kasei Co., Ltd.

[0618] The stabilizer is used in the liquid crystal composition containing the pigment compound in one or more types, preferably one to five types, preferably one to four types, preferably one to three types, and preferably one to two types.

[0619] When a stabilizer is used, the lower limit of the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 0.01% by mass or more, preferably 0.05% by mass or more, and preferably 0.1% by mass or more.

[0620] When a stabilizer is used, the upper limit of the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 2.0% by mass or less, preferably 1.5% by mass or less, and preferably 1.0% by mass or less.

[0621] When a stabilizer is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 0.01% by mass to 2.0% by mass, preferably 0.05% by mass to 1.5% by mass, and preferably 0.1% by mass to 1.0% by mass.

[0622] When a stabilizer is used, the lower limit of the amount of the stabilizer added is preferably 0.01 parts by mass or more, preferably 0.05 parts by mass or more, and preferably 0.1 parts by mass or more, based on 100 parts by mass of the liquid crystal composition not containing a pigment compound and an additive.

[0623] When a stabilizer is used, the upper limit of the amount of the stabilizer added is preferably 2.0 parts by mass or less, preferably 1.5 parts by mass or less, and preferably 1.0 parts by mass or less, based on 100 parts by mass of the liquid crystal composition not containing a pigment compound and an additive.

[0624] When a stabilizer is used, the amount of the stabilizer added is preferably 0.01 to 2.0 parts by mass, preferably 0.05 to 1.5 parts by mass, and preferably 0.1 to 1.0 parts by mass based on 100 parts by mass of the liquid crystal composition not containing a pigment compound and additives.

[0625] In addition, by using a chiral agent in a liquid crystal composition containing a pigment compound, a twist can be induced in the liquid crystal.

[0626] The chiral agent can be either right-handed or left-handed, as long as they are used separately according to the structure of the element.

[0627] In addition, as the chiral agent, a chiral agent used in a twisted nematic (TN) mode or a super twisted nematic (STN) mode may be used instead.

[0628] For example, as the chiral agent, "Chiral S-811 (a compound represented by the following structural formula (CA-1))" and the like can be cited.

[0629] [Chemistry 79]

[0630]

[0631] In the structural formula (CA-1), "*" represents an uneven center.

[0632] The chiral agent is used in the liquid crystal composition containing the pigment compound in 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.

[0633] When a chiral agent is used, the lower limit of the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 0.05% by mass or more, preferably 0.1% by mass or more, preferably 0.3% by mass or more, and preferably 0.5% by mass or more.

[0634] When a chiral agent is used, the upper limit of the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 5% by mass or less, preferably 3.0% by mass or less, preferably 2.0% by mass or less, and preferably 1.5% by mass or less.

[0635] When a chiral agent is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition containing the pigment compound is preferably 0.05% by mass to 5% by mass, preferably 0.1% by mass to 3.0% by mass, preferably 0.3% by mass to 2.0% by mass, and preferably 0.5% by mass to 1.5% by mass.

[0636] When a chiral agent is used, the lower limit of the amount of the chiral agent added relative to 100 parts by mass of the liquid crystal composition containing no pigment compound and no additives is preferably 0.05 parts by mass or more, preferably 0.1 parts by mass or more, preferably 0.3 parts by mass or more, and preferably 0.5 parts by mass or more.

[0637] When a chiral agent is used, the upper limit of the amount of the chiral agent added relative to 100 parts by mass of the liquid crystal composition containing no pigment compound and additives is preferably 5 parts by mass or less, preferably 3.0 parts by mass or less, preferably 2.0 parts by mass or less, and preferably 1.5 parts by mass or less.

[0638] When a chiral agent is used, the amount of the chiral agent added is preferably 0.05 to 5 parts by mass, preferably 0.1 to 3.0 parts by mass, preferably 0.3 to 2.0 parts by mass, and preferably 0.5 to 1.5 parts by mass relative to 100 parts by mass of the liquid crystal composition not containing a pigment compound and additives.

[0639] In order to achieve both high light resistance and high solubility of the liquid crystal composition containing the pigment compound, the content of the compound represented by the general formula (i) and / or the general formula (ii) is preferably 10% by mass or more, preferably 10% to 20% by mass.

[0640] In addition, the content relationship can also be applied to any subordinate concepts of the compounds represented by general formula (i) and / or the compounds represented by general formula (ii), and can also be applied to any combination of the compounds represented by general formula (i) and / or the compounds represented by general formula (ii) including the subordinate concepts.

[0641] In addition, from the viewpoint of achieving both high light resistance and high solubility of a liquid crystal composition containing a pigment compound, when using a compound represented by the general formula (iii), the total content of the compound represented by the general formula (i), the compound represented by the general formula (ii) and the compound represented by the general formula (iii) is preferably 20% by mass or more, preferably 25% by mass to 65% by mass, preferably 30% by mass to 60% by mass, and preferably 35% by mass to 55% by mass in 100% by mass of the liquid crystal composition containing the pigment compound.

[0642] In addition, the content relationship can also be applied to any subordinate concepts of the compound represented by general formula (i), the compound represented by general formula (ii) and / or the compound represented by general formula (iii), and can also be applied to any combination of the compound represented by general formula (i), the compound represented by general formula (ii) and / or the compound represented by general formula (iii) including the subordinate concepts.

[0643] In addition, from the viewpoint of achieving both high light resistance and high solubility of a liquid crystal composition containing a pigment compound, when using a compound represented by general formula (iv), the total content of the compound represented by general formula (i), the compound represented by general formula (ii) and the compound represented by general formula (iv) is preferably 20% by mass or more in 100% by mass of the liquid crystal composition containing the pigment compound, preferably 25% by mass to 75% by mass, preferably 30% by mass to 70% by mass, and preferably 35% by mass to 65% by mass.

[0644] In addition, the content relationship can also be applied to any subordinate concepts of the compound represented by the general formula (i), the compound represented by the general formula (ii) and / or the compound represented by the general formula (iv), and can also be applied to any combination of the compound represented by the general formula (i), the compound represented by the general formula (ii) and / or the compound represented by the general formula (iv) including the subordinate concepts.

[0645] The upper limit temperature of the liquid crystal phase (T NI) is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase.

[0646] Just T NI From the viewpoint that the higher the temperature, the nematic phase can be maintained at a higher temperature, and a wider driving temperature range can be obtained, the upper limit temperature of the liquid crystal phase of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention (T NI ) is preferably above 95°C, preferably 100°C to 150°C, and preferably 100°C to 130°C.

[0647] Liquid crystal phase lower limit temperature (T →N ) is the temperature at which a liquid crystal composition undergoes a phase transition from other phases (glass, smectic phase, crystalline phase) to the nematic phase.

[0648] Just T →N The lower the temperature, the nematic phase can be maintained at a lower temperature, and thus a wider driving temperature range can be obtained. The lower limit temperature (T →N ) is preferably below -15°C, preferably -78°C to -20°C, and preferably -65°C to -25°C.

[0649] The refractive index anisotropy (Δn) of the liquid crystal composition used in the pigment compound-containing liquid crystal composition of the present invention at 25° C. and 589 nm is preferably 0.05 or more, preferably 0.06 to 0.20, preferably 0.07 to 0.15, and preferably 0.08 to 0.13.

[0650] The refractive index (n) of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention in the long axis direction of the liquid crystal molecules at 25° C. and 589 nm is e ) is preferably greater than 1.4, preferably 1.45 to 1.65, and preferably 1.50 to 1.63.

[0651] The refractive index (n) of the liquid crystal molecule in the short axis direction of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention at 25° C. and 589 nm is o ) is preferably greater than 1.3, preferably 1.35 to 1.55, and preferably 1.40 to 1.53.

[0652] In addition, the n of the liquid crystal composition used in the liquid crystal composition containing the pigment compound can be measured using an Abbe refractometer. e 、n o , calculate Δn.

[0653] The dielectric anisotropy (Δε) of the liquid crystal composition used in the pigment compound-containing liquid crystal composition of the present invention at 25° C. is preferably positive (2≦Δε).

[0654] More specifically, the dielectric anisotropy (Δε) of the liquid crystal composition used in the pigment compound-containing liquid crystal composition of the present invention at 25° C. is preferably 2.0 to 20.0, preferably 2.5 to 15.0, preferably 3.0 to 10.0, preferably 3.5 to 7.0, and preferably 4.0 to 6.0.

[0655] The dielectric constant (ε) of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention in the long axis direction of the liquid crystal molecules at 25°C is / / ) is preferably 5.0 or more, preferably 5.5 to 30.0, preferably 6.0 to 20.0, preferably 6.0 to 15.0, and preferably 6.5 to 10.0.

[0656] The dielectric constant (ε) of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention in the short axis direction of the liquid crystal molecules at 25°C is ⊥ ) is preferably 1.5 or more, preferably 2.0 to 7.0, preferably 2.5 to 5.0, and preferably 2.5 to 4.0.

[0657] The rotational viscosity (γ) of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention at 25°C is 1 ) is preferably 100mPa·s~180mPa·s, preferably 105mPa·s~175mPa·s, preferably 110mPa·s~170mPa·s, preferably 115mPa·s~165mPa·s.

[0658] The elastic constant K at 25° C. of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention is 11 It is preferably 1.0 pN to 30.0 pN, preferably 5.0 pN to 25.0 pN, and preferably 10.0 pN to 20.0 pN.

[0659] The elastic constant K at 25° C. of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention is 22 It is preferably 1.0 pN to 25.0 pN, preferably 3.0 pN to 20.0 pN, and preferably 5.0 pN to 15.0 pN.

[0660] The elastic constant K at 25° C. of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention is 33 It is preferably 1.0 pN to 35.0 pN, preferably 5.0 pN to 30.0 pN, and preferably 10.0 pN to 25.0 pN.

[0661] (element)

[0662] Next, a device using the above-mentioned liquid crystal composition containing the pigment compound will be described.

[0663] As the use of the element, a light-adjusting element is preferred.

[0664] The structure of the element is preferably a structure in which a substrate having a first transparent electrode layer and a substrate having a second transparent electrode layer are arranged to face each other with the transparent electrode layers facing inside, and the liquid crystal composition is sandwiched between the substrates.

[0665] As the transparent electrode layer, an ITO electrode is preferable.

[0666] The substrate having the first transparent electrode layer and / or the second transparent electrode layer may include an alignment film on the transparent electrode layer.

[0667] As the alignment film, an alignment film for horizontal alignment is preferable.

[0668] In addition, by adding a chiral agent to a liquid crystal composition containing a pigment compound, the liquid crystal can be twisted and aligned.

[0669] From the viewpoint of improving absorbance, when a chiral agent is added, the twist of the liquid crystal molecules in the liquid crystal composition containing the pigment compound is preferably 180° or more, preferably 180° to 720°, preferably 270° to 540°, and preferably 270° to 450°.

[0670] The twist of the liquid crystal molecules can also be adjusted by adjusting the angle of the alignment axis by configuring the substrate having the first transparent electrode layer and the substrate having the second transparent electrode layer.

[0671] When a chiral agent is added, the twist pitch (p) in the liquid crystal composition containing the pigment compound is preferably 2 μm to 30 μm, more preferably 5 μm to 20 μm.

[0672] The twist pitch (p) can be calculated from the tilt angle θ (tilt of the substrate on the upper surface) of the wedge-shaped liquid crystal cell and the interval L of the disclination lines of the wedge-shaped liquid crystal cell measured by a length meter, by injecting a liquid crystal composition containing a specified amount of a chiral agent into an antiparallel rubbed wedge-shaped liquid crystal cell having two substrates and a slowly changing cell thickness, and obtaining p=2×L×tanθ.

[0673] The d / p value, which is the relationship between the twist pitch (p) and the cell thickness (d), is preferably 0.1 to 2.2, more preferably 0.5 to 1.5.

[0674] Specifically, it is preferable to adjust the relationship between the twist pitch (p) and the cell thickness (d) according to the twist angle so that the value d / p becomes optimal.

[0675] The most preferred d / p value is a region where no orientation defects such as reverse twist domains or stripe domains occur.

[0676] It is preferred to observe the field visually or with a microscope and perform adjustments so that no alignment defect occurs.

[0677] The pretilt angle of the liquid crystal composition containing the pigment compound in the device is preferably 0.1° to 10°, more preferably 0.5° to 5°.

[0678] The pretilt angle can be measured using OPTIPRO manufactured by Shintech.

[0679] The interval (cell thickness) between the substrates is preferably 1 μm to 100 μm, preferably 1.5 μm to 30 μm, and preferably 5 μm to 20 μm.

[0680] The spacing between the substrates can also be adjusted using spacers.

[0681] Examples of the spacer include glass particles, plastic particles, alumina particles, and photoresist materials.

[0682] Furthermore, from the viewpoint of preventing degradation due to ultraviolet rays, the element of the present invention may include an ultraviolet cutoff film.

[0683] For example, an ultraviolet (UV) cutoff film that cuts off light having a wavelength of 400 nm or less may be laminated or attached to the element.

[0684] The element of the present invention may be used in the form of a single layer, or a plurality of elements may be stacked in two or three layers.

[0685] When a plurality of elements are stacked for use, from the viewpoint of improving contrast, it is preferred that the elements subjected to antiparallel alignment treatment be stacked so that the alignment treatment directions are orthogonal to each other by 90°.

[0686] The element can be made as follows.

[0687] For example, a sealant such as an epoxy-based thermosetting composition is formed on a substrate having a first transparent electrode layer with an injection port, a substrate having a second transparent electrode layer and the substrate are bonded together, and then heated to thermally cure the sealant, thereby producing an empty cell.

[0688] Then, a liquid crystal element can be produced by sandwiching a liquid crystal composition containing a dye compound between two substrates in the cell using a common vacuum injection method or a One Drop Fill (ODF) method.

[0689] Furthermore, in order to further improve the contrast, an optical film having a polarization axis or the like may be further disposed on the element at a predetermined angle.

[0690] Example

[0691] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

[0692] The compositions of the following Examples and Comparative Examples contain each compound at the ratio shown in the table, and the content is described in "mass %".

[0693] In addition, the following abbreviations are used in describing compounds. In addition, unless otherwise specified, a compound that can take a cis-isomer and a trans-isomer means a trans-isomer.

[0694] <Ring structure>

[0695] [Chemistry 80]

[0696]

[0697] <Terminal structure>

[0698] [Table 1]

[0699] abbreviation Chemical structure -n -CnH2n+1 n- CnH2n+1- -On -OCnH2n+1 nO- CnH2n+1O- -F -F -CN -CN -V -CH=CH2 V- CH2=CH- -2V -CH2-CH2-CH=CH2 V2- CH2=CH-CH2-CH2- -V1 -CH=CH-CH3 1V- CH3-CH=CH-

[0700] (In the table, n is a natural number.)

[0701] <Connection structure>

[0702] [Table 2]

[0703] abbreviation Chemical structure - single bond -n- -CnH2n- -E1- -C(=O)-O- -E2- -OC(=O)-

[0704] <Pigment compounds>

[0705] SI-426: Red dichroic pigment compound (azo system), maximum absorption wavelength 414 nm

[0706] SI-486: Yellow dichroic pigment compound (azo system), maximum absorption wavelength 513 nm

[0707] ·G-472: Blue dichroic pigment compound (azo system), maximum absorption wavelength 636 nm

[0708] <Antioxidants>

[0709] IRGANOX 1076: Hindered phenol antioxidant

[0710] <Ultraviolet (UV) absorber>

[0711] Kemisorb 71: Benzotriazole compounds

[0712] <Physical properties of liquid crystal composition used in liquid crystal composition containing pigment compound>

[0713] The following physical property values ​​were measured for the liquid crystal composition used in the liquid crystal composition containing the pigment compound.

[0714] T NI (°C): The temperature at which the liquid crystal composition changes from the nematic phase to the isotropic phase (upper limit temperature)

[0715] T →N (°C): The temperature at which a liquid crystal composition changes from other phases to the nematic phase (lower limit temperature)

[0716] Δn: refractive index anisotropy of the liquid crystal composition at 25°C and 589 nm

[0717] n e : The refractive index of the liquid crystal molecules in the long axis direction of the liquid crystal composition at 25°C and 589nm

[0718] n o : The refractive index of the liquid crystal molecules in the short axis direction of the liquid crystal composition at 25°C and 589nm

[0719] Δε: Dielectric anisotropy of the liquid crystal composition at 25°C

[0720] ε / / : Dielectric constant of the liquid crystal composition in the long axis direction of the liquid crystal molecules at 25°C

[0721] ε ⊥ : Dielectric constant of the liquid crystal molecules in the short axis direction of the liquid crystal composition at 25°C

[0722] γ 1 (mPa·s): Rotational viscosity at 25°C

[0723] K 11 (pN): elastic constant K of the liquid crystal composition at 25°C 11

[0724] K 22 (pN): elastic constant K of the liquid crystal composition at 25°C 22

[0725] K 33 (pN): elastic constant K of the liquid crystal composition at 25°C 33

[0726] (Example 1 to Example 18 and Comparative Example 1 to Comparative Example 2)

[0727] <Preparation of Liquid Crystal Composition Used in Liquid Crystal Composition Containing Pigment Compound>

[0728] As described in Table 1, the liquid crystal compounds were mixed at various ratios to prepare liquid crystal compositions LC-1 to LC-11 for use in liquid crystal compositions containing pigment compounds, and the physical properties thereof were measured.

[0729] [Table 3]

[0730] Liquid crystal compounds LC-1 LC-2 LC-3 LC-4 LC-5 LC-6 LC-7 LC-8 LC-9 LC-10 LC-11 V2-Cy-Cy-Ph-1 15 V-Cy-Cy-Ph-1 15 15 20 15 15 15 15 15 15 3-Cy-Cy-Ph3-F 14 14 15 14 14 10 14 14 14 V-Cy-Cy-Ph3-F 4 V2-Cy-Cy-Ph3-F 14 3-Cy-Ph-Ph35-F 15 15 15 12 15 15 15 15 15 2-Ph-Ph3-Ph35-F 8 5 11 8 8 8 8 8 8 3-Cy-Ph3-Ph35-F 15 3-Cy-Ph-O1 15 16 12 3-Cy-Ph-O2 12 12 16 12 12 12 12 12 12 3-Cy-Ph35-CN 10 5-Cy-E1-Ph3-F 8 3-Cy-Cy-E1-Ph3-F 5 5 5 5 5 5 5 5 5 3-Cy-2-Cy-E1-Ph3-F 7 5 4-Cy-2-Cy-E1-Ph3-F 6 5 2-Cy-Cy-Ph-Ph3-F 4 4 4 4 4 4 4 4 4 4 3-Cy-Cy-Ph-Ph3-F 4 4 4 4 4 4 4 4 4 4 3-Cy-Cy-V 15 15 15 15 27 15 15 3-Cy-Cy-Ph-1 5 4 3-Cy-Cy-Ph-3 7 3-Cy-Ph-Ph-1 5 8 3-Cy-Cy-E1-Ph-Cy-2 4 4 4 4 4 4 4 4 4 4 4 3-Cy-Cy-E1-Ph-Cy-4 4 4 4 4 4 4 4 4 4 4 4 3-Cy-Cy-2 15 3-Cy-Cy-V1 15 Total (mass %) 100 100 100 100 100 100 100 100 100 100 100

[0731] [Table 4]

[0732]

[0733] <Production of components and light resistance and solubility tests>

[0734] As shown in Tables 5 and 6, a pigment compound, an antioxidant, and a chiral agent are mixed and dissolved in LC1 to LC11 to prepare a liquid crystal composition containing a pigment compound. Next, two 2cm×2cm glass substrates having an ITO electrode and an orientation film (AL1051) for horizontal orientation on the ITO electrode are used to prepare a unit having an ITO electrode layer as the inner side of the unit, a unit thickness adjusted to 10μm by plastic particles, and an injection port. A liquid crystal composition containing a pigment compound is injected into the unit, and the injection port is blocked with a sealing material to prepare an element. Then, the prepared element is used to perform a (light resistance test) and a (solubility test). The results are shown in Tables 5 and 6.

[0735] In addition, the addition amount (mass parts) of the pigment compound, antioxidant, and chiral agent in Table 5 and Table 6 shows the addition amount relative to 100 mass parts of the liquid crystal composition.

[0736] (Solubility test)

[0737] The produced element was stored in a thermostatic chamber at -25°C and visually observed every 48 hours to see if there was any precipitation for 500 hours.

[0738] The evaluation criteria are as follows.

[0739] A: No precipitation was observed until 500 hours or later.

[0740] B: Precipitation was observed during a period of 250 hours to less than 500 hours.

[0741] C: Precipitation was observed during the period from 0 hour to less than 250 hours.

[0742] (Light resistance test)

[0743] The produced element was irradiated for 500 hours with 100,000 Lux of light through a UV cut film for cutting off light with a wavelength of 400 nm or less using "SUNTEST" manufactured by ATLAS under an output of 760 W, and the change in color tone (degree of deterioration) was visually observed.

[0744] The evaluation criteria are as follows.

[0745] A: No change in color tone was observed until 500 hours or later.

[0746] B: Change in color tone was observed between 250 hours and less than 500 hours.

[0747] C: Change in color tone was observed during the period from 0 hour to less than 250 hours.

[0748] [Table 5]

[0749]

[0750] [Table 6]

[0751]

[0752] According to Examples 1 to 9 and Comparative Examples 1 and 2, it was found that a device having excellent light resistance and solubility can be obtained by using one or more predetermined alkenyl compounds and a compound having a predetermined difluorinated structure in combination.

[0753] In addition, according to Examples 10 to 18, the same effect was confirmed even when an antioxidant or a chiral agent was used in combination.

[0754] Furthermore, according to Examples 1 to 7, 8 to 9, 10 to 16, and 17 to 18, in addition to combining one or more of the specified alkenyl compounds and the compound having a specified difluoro structure, one or more of the compounds having a trifluoro structure represented by the general formula (iii) and one or more of the compounds represented by the following general formula (iv) having a cyclohexane ring and a benzene ring are also combined, and it is found that the light resistance is better.

[0755] Industrial Applicability

[0756] The liquid crystal composition of the present invention can be used in a device, particularly a light-adjusting device.

Claims

1. A liquid crystal composition containing a pigment compound, comprising: One or more compounds represented by the following structural formulas (i-1.1) to (i-1.8); One or more compounds represented by the following structural formulas (ii-1.1) to (ii-1.4); One or more compounds represented by the following structural formula (iii-1.1), structural formula (iii-2.1), and structural formula (iii-3.1); One or more compounds represented by the following structural formulas (iv-1.1) to (iv-1.5); One or more of the compounds represented by the following structural formulas (vi-1-1.1) to (vi-1-1.8), (vi-2-1.1) to (vi-2-1.4), (vi-2-2.1) to (vi-2-2.5), and (vi-3-1.1) to (vi-3-1.3); and One or more pigment compounds, The total content of the compounds represented by the structural formula (i-1.1) to the structural formula (i-1.8) in 100% by mass of the liquid crystal composition containing the pigment compound is 10% by mass to 25% by mass. The total content of the compounds represented by the structural formula (ii-1.1) to the structural formula (ii-1.4) in 100% by mass of the liquid crystal composition containing the pigment compound is 10% by mass to 20% by mass. The total content of the compounds represented by the structural formula (iii-1.1), the structural formula (iii-2.1) and the structural formula (iii-3.1) in 100% by mass of the liquid crystal composition containing the pigment compound is 10% by mass to 25% by mass, The total content of the compounds represented by the structural formula (iv-1.1) to the structural formula (iv-1.5) in 100% by mass of the liquid crystal composition containing the pigment compound is 5% by mass to 35% by mass, The total content of the compounds represented by (vi-1-1.1) to (vi-1-1.8), (vi-2-1.1) to (vi-2-1.4), (vi-2-2.1) to (vi-2-2.5), and (vi-3-1.1) to (vi-3-1.3) in 100% by mass of the liquid crystal composition containing the pigment compound is 5% to 50% by mass.

2. The liquid crystal composition containing a pigment compound according to claim 1, further comprising one or more compounds represented by the following general formula (v): In the general formula (v), R v1 represents an alkyl group having 1 to 20 carbon atoms, One or more -CH 2 - may be independently substituted by -O- and / or -CO-, One or more -CH 2 -CH 2 - may be independently substituted by -CH=CH- and / or -C≡C-, 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. R v2 represents any one of a halogen atom, -CN, -OCN or -C≡CCN, A v1 and A v2 Each independently represents a group (a), a group (b) and a group (c) selected from the following: (a) 1,4-cyclohexylene, wherein one -CH 2 - or two or more non-adjacent -CH 2 - may be substituted by -O- and / or -S- (b) 1,4-phenylene, wherein one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N= (c) naphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl, wherein one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl may be substituted with -N= The basis of the group is The A v1 and A v2 One or more hydrogen atoms in the group may be independently replaced by halogen atoms. Z v1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH 2 - can be independently -O-, -CH(CH 3 )-, -CO- and / or -CF 2 -replace, One or more -CH 2 -CH 2 - can be independently -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -CH=C(CH 3 )-、-C(CH 3 )=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C-, Oxygen atoms do not bond directly to each other. n v1 represents an integer from 1 to 3, In the presence of multiple A v2 and Z v1 In the case of , these may be respectively the same or different; in, The compounds represented by structural formula (ii-1.1) to structural formula (ii-1.4), structural formula (iii-1.1), structural formula (iii-2.1) and structural formula (iii-3.1) are excluded.

3. The liquid crystal composition containing a pigment compound according to claim 1 or 2, in, The pigment compound has maximum absorption between 350nm and 700nm.

4. The liquid crystal composition containing a pigment compound according to claim 3, in, The pigment compound is a dichroic pigment compound. 5 . The liquid crystal composition containing a pigment compound according to claim 1 , further comprising a chiral agent. 6 . A device using the liquid crystal composition containing a pigment compound according to claim 1 .

7. The element according to claim 6, in, The element is a dimming element.

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