Light-modulating element and liquid-crystal composition containing anthraquinone compound

Abstract

Disclosed is a liquid-crystal composition containing (A) a dye compound and (B) a liquid crystal material, wherein the (A) dye compound includes: (i) an anthraquinone compound represented by general formula (1) (where in the formula, R1 and R4 each independently represent a hydrogen atom, a straight-chain alkyl group having 1 to 12 carbon atoms or a branched-chain alkyl group having 3 to 12 carbon atoms, a straight-chain alkoxy group having 1 to 12 carbon atoms or a branched-chain alkoxy group having 3 to 12 carbon atoms, a cyano group, etc.; R2, R3, R5, and R6 each usually independently represent a hydrogen atom, a straight-chain alkyl group having 1 to 4 carbon atoms or a branched-chain alkyl group having 3 to 4 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms or a branched-chain alkoxy group having 3 to 4 carbon atoms, a cyano group, etc., but R2, R3, R5, and R6 may all represent hydrogen atoms); and (ii) an anthraquinone compound represented by general formula (2).

Description

Liquid crystal composition containing anthraquinone compound and light-modulating element

[0001] The present invention relates to a novel liquid crystal composition and a light-adjusting element using the same.

[0002] Various proposals have been made for light-controlling films that control the transmission of external light for purposes such as protecting privacy in windows, doors, and partitions in vehicles such as trains and automobiles, and in buildings such as business buildings and hospitals (see Patent Documents 1 and 2). One such light-controlling film uses liquid crystal. Typically, liquid crystal light-controlling films can block visibility by controlling the transmission and scattering of light depending on whether or not a voltage is applied, but they cannot block light itself, and therefore tend to increase glare due to light scattering. Therefore, attempts have been made to use dyes as materials for light-controlling panels with the aim of reducing glare and improving contrast (see Patent Documents 3 and 4). When such light-controlling panels are used in automotive windowpanes, there is a growing demand for black elements that can block visible light from the perspectives of practicality and design. Such black light-controlling elements are strongly required to have a high contrast with and without the application of voltage, to be close to achromatic both with and without the application of voltage, and to exhibit minimal change in color when exposed to light for long periods of time during outdoor use, i.e., at high temperatures.

[0003] Dichroic dyes are commonly used as dyes in liquid crystal light control films. Known light control elements using liquid crystal compositions containing dichroic dyes include the guest-host (GH) system and the polymer-dispersed liquid crystal (PDLC) system, in which a dye and liquid crystal composition is dispersed in a polymer. Various dichroic dyes have been proposed for each system (see Patent Documents 4, 5, 6, and 7).

[0004] Dichroic dyes commonly used in liquid crystal compositions for light-adjusting devices are required to have a dichroic ratio sufficient to enhance contrast when used in a device, as well as light resistance, UV resistance, heat resistance, and compatibility (solubility) of the dichroic dye with the components of the liquid crystal composition. Although efforts have been made to improve these properties, none have yet met market demands. For example, Patent Documents 4 and 7 disclose dichroic dye compositions suitable for light-adjusting applications. However, both exhibit significant hue changes upon prolonged exposure to light, and are therefore not sufficiently lightfast for outdoor use. Furthermore, the dichroic dye described in Patent Document 7 has a low dichroic ratio, making it impractical. There is a strong demand for light-adjusting devices that combine sufficient light resistance for outdoor use with a high dichroic ratio.

[0005] Japanese Patent Publication No. 63-501512, Japanese Patent Laid-Open No. 03-47392, Japanese Patent Laid-Open No. 2018-205746, Japanese Patent Laid-Open No. 2011-190314, Japanese Patent Laid-Open No. 62-5941, International Publication No. 2021 / 261181, Japanese Patent Publication No. 03-063589

[0006] An object of the present invention is to provide a liquid crystal composition that can provide a light-controlling device having a high dichroic ratio, an achromatic color, and excellent light resistance.

[0007] As a result of extensive investigations, the present inventors have found that the above object can be achieved by using two types of dichroic dyes having specific structures in combination in a liquid crystal composition, and have thus completed the present invention.

[0008] Aspects or embodiments of the present invention can be summarized as follows: [1] A liquid crystal composition containing (A) a dye compound and (B) a liquid crystal material, wherein the dye compound (A) is represented by the following general formula (1): (In the formula, R １ and R ４ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR９ , a cyano group, or a trifluoromethyl group; R ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, provided that R １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ２ , R ３ , R ５ , R ６ each represents a hydrogen atom; R ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １０ When a plurality of R are present, they may be the same or different. １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ７ , R ８ each independently represents a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a substituent represented by the above formula (a); R ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R１１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; R １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １２ (ii) an anthraquinone compound represented by the following general formula (2): (In the formula, R １３ represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a linear alkoxy group having 1 to 12 carbon atoms, or a branched alkoxy group having 3 to 12 carbon atoms; R １４ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; provided that R １ and R ４ When one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms, R １３ represents a hydrogen atom or a branched alkyl group having 4 to 10 carbon atoms, which may be a linear alkyl group having 4 to 10 carbon atoms or a cyclic alkyl group having 4 to 10 carbon atoms; R １４ [2] A liquid crystal composition comprising an anthraquinone compound represented by the formula (1), wherein R in formula (1) represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 4 carbon atoms. １ and R ４ each independently represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a fluorine atom, a chlorine atom, -CO２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, and R ２ , R ３ , R ５ and R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a fluorine atom, a chlorine atom, or —CO ２ R ９ , -COR ９ , a cyano group, or a trifluoromethyl group, and R ９ are each independently a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms. [3]. A liquid crystal composition comprising the anthraquinone compound according to the above item [1], １３ is a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms, or a linear alkoxy group having 1 to 10 carbon atoms or a branched alkoxy group having 3 to 10 carbon atoms. [4]. The liquid crystal composition according to any one of items [1] to [3] above, wherein the mass ratio of the anthraquinone compound represented by general formula (1) to the anthraquinone compound represented by general formula (2) is 2:1 to 1:2. [5]. The liquid crystal composition according to any one of items [1] to [4] above, wherein the content of the dye compound (A) in the liquid crystal composition is 0.5 to 10 parts by mass per 100 parts by mass of the liquid crystal material (B). [6]. The liquid crystal composition according to any one of items [1] to [5] above, comprising a dichroic dye other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2). [7]. A light-controlling element comprising a pair of substrates arranged opposite to each other, at least one of which is a transparent substrate having a transparent electrode, and a liquid crystal composition according to any one of the above items [1] to [6] sandwiched between the pair of substrates. [8] The light-controlling element according to the above item [7], wherein both of the pair of substrates are transparent substrates having transparent electrodes.

[0009] By using the liquid crystal composition of the present invention, a light-controlling device having an achromatic color, high contrast and excellent light resistance can be obtained.

[0010] The present invention is described in detail below. In this specification, the term "lower limit value to upper limit value" means that both the lower limit value and the upper limit value are included. In this specification, an "anthraquinone compound" may be simply referred to as a "compound." In addition, in this specification, in accordance with common chemical knowledge, a "branched" hydrocarbyl substituent may include a "cyclic" hydrocarbyl substituent (i.e., a residue obtained by removing one hydrogen atom from a cyclic hydrocarbyl group).

[0011] The liquid crystal composition of the present invention contains (A) a dye compound and (B) a liquid crystal material. The dye compound (A) contains both at least one anthraquinone compound represented by the following general formula (1) and at least one anthraquinone compound represented by the following general formula (2):

[0012] In the anthraquinone compound represented by the general formula (1), R １ and R ４ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group; R ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, provided that R １ and R ４When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ２ , R ３ , R ５ , R ６ each represents a hydrogen atom; R ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １０ When a plurality of R are present, they may be the same or different. １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ７ , R ８ each independently represents a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a substituent represented by the above formula (a); R ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R １１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; R １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １２ When a plurality of groups are present, they may be the same or different.

[0013] In the anthraquinone compound represented by the general formula (2), R １３ represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a linear alkoxy group having 1 to 12 carbon atoms, or a branched alkoxy group having 3 to 12 carbon atoms; R １４ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; provided that R １ and R ４ When one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms, R １３ represents a hydrogen atom or a branched alkyl group having 4 to 10 carbon atoms, which may be a linear alkyl group having 4 to 10 carbon atoms or a cyclic alkyl group having 4 to 10 carbon atoms; R １４ represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 or 4 carbon atoms.

[0014] In general formula (1), R １ , R ４ Specific examples of the linear alkyl group having 1 to 12 carbon atoms represented by R include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, and an n-dodecyl group. Methyl group, ethyl group, n-propyl group, n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group are preferred, and an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group are more preferred. １ , R ４Specific examples of the branched alkyl group having 3 to 12 carbon atoms represented by include an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an isopentyl group, an isohexyl group, a t-pentyl group, a 2-methylpentyl group, a 2-methylhexyl group, a 2-methylheptyl group, a 3-methylbutyl group, a 3-methylpentyl group, a 3-methylhexyl group, a 3-methylheptyl group, a 2-ethylpropyl group, a 2-ethylbutyl group, a 2-ethylhexyl group, a 2-propylhexyl group, a 2-butylhexyl group, a 2-pentylhexyl group, and a 2-pentylheptyl group, etc. An isobutyl group, a sec-butyl group, a t-butyl group, and a 2-ethylhexyl group are preferred.

[0015] In general formula (1), R １ , R ４ Specific examples of the linear alkoxy group having 1 to 12 carbon atoms or the branched alkoxy group having 3 to 12 carbon atoms represented by R include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, an n-pentyloxy group, an iso-pentyloxy group, a neo-pentyloxy group, a t-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, an n-undecyloxy group, and an n-dodecyloxy group. １ , R ４ When one of R is a cyano group and the other is a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, the alkoxy group is preferably a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, and more preferably a linear alkoxy group having 1 to 4 carbon atoms. １ , R ４ is not a cyano group, and R １ , R ４ When at least one of the above is a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, the alkoxy group is preferably a linear or branched alkoxy group having 4 to 10 carbon atoms, and more preferably a linear or branched alkoxy group having 4 to 8 carbon atoms.

[0016] In general formula (1), R １ and R ４ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom (particularly a fluorine atom or a chlorine atom), -CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a fluorine atom, a chlorine atom, —CO ２ R ９ , -COR ９ , a cyano group, or a trifluoromethyl group is more preferred. １ and R ４ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a fluorine atom, a chlorine atom, -CO ２ R ９ , -COR ９ or a cyano group is even more preferred.

[0017] In general formula (1), R ２ , R ３ , R ５ , and R ６ Specific examples of the linear alkyl group having 1 to 4 carbon atoms or the branched alkyl group having 3 or 4 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, etc. A methyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group are preferred.

[0018] In general formula (1), R ２ , R ３ , R ５、 and R６ Examples of the linear alkoxy group having 1 to 4 carbon atoms or the branched alkoxy group having 3 or 4 carbon atoms represented by the formula (1) include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, etc. A methoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, and a t-butoxy group are preferred.

[0019] In the general formula (1), (R １ and R ４ and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms) ２ , R ３ , R ５、 and R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -COR ９ , a cyano group, or a trifluoromethyl group, and a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms, a fluorine atom, a chlorine atom, —CO ２ R ９ , -COR ９ , a cyano group, or a trifluoromethyl group is more preferred; a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms is preferred; a fluorine atom, a chlorine atom, —CO ２ R ９ , -COR ９ or a cyano group is even more preferred.

[0020] In general formula (1), R １ ~R ６ Examples of the halogen atom that can be taken by include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. A fluorine atom is preferred.

[0021] In general formula (1), R ７ , R ８Among the linear alkyl groups having 1 to 12 carbon atoms or branched alkyl groups having 3 to 12 carbon atoms represented by the formula (I), specific examples of the linear alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, and an n-dodecyl group. Methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, and n-heptyl groups are preferred, and an n-butyl, n-pentyl, n-hexyl, and n-heptyl groups are more preferred. Specific examples of branched alkyl groups include an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an isopentyl group, a t-pentyl group, an isohexyl group, a 2-methylpentyl group, a 2-methylhexyl group, a 2-methylheptyl group, a 3-methylbutyl group, a 3-methylpentyl group, a 3-methylhexyl group, a 3-methylheptyl group, a 2-ethylpropyl group, a 2-ethylbutyl group, a 2-ethylhexyl group, a 2-propylhexyl group, a 2-butylhexyl group, a 2-pentylhexyl group, and a 2-pentylheptyl group, etc. An isobutyl group, a sec-butyl group, and a t-butyl group are preferred.

[0022] In general formula (1), R ７ , R ８ Specific examples of the linear alkoxy group having 1 to 12 carbon atoms or the branched alkoxy group having 3 to 12 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, an n-pentyloxy group, an iso-pentyloxy group, a neo-pentyloxy group, a t-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, an n-undecyloxy group, an n-dodecyloxy group, etc. A linear or branched alkoxy group having 1 to 10 carbon atoms is preferred, and a linear alkoxy group having 1 to 7 carbon atoms is more preferred.

[0023] In the general formula (1), (R １ and R ４and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms) ７ , R ８ are each independently a linear alkoxy group having 1 to 12 carbon atoms or a substituent represented by formula (a). １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ７ , R ８ are preferably each independently a linear alkoxy group having 4 to 10 carbon atoms or a substituent represented by formula (a).

[0024] In the formulas (a) to (c) representing the moieties in the general formula (1), R １０ ~R １２ Among the linear alkyl groups having 1 to 8 carbon atoms or branched alkyl groups having 3 to 8 carbon atoms represented by the formula (I), specific examples of the linear alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. Methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, and n-heptyl groups are preferred, and an n-propyl, n-butyl, n-pentyl, n-hexyl, and n-heptyl groups are particularly preferred. Specific examples of branched alkyl groups include an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an isopentyl group, a t-pentyl group, an isohexyl group, a 2-methylpentyl group, a 2-methylhexyl group, a 2-methylheptyl group, a 3-methylbutyl group, a 3-methylpentyl group, a 3-methylhexyl group, a 3-methylheptyl group, a 2-ethylpropyl group, a 2-ethylbutyl group, a 2-ethylhexyl group, etc. An isopropyl group, an isobutyl group, a sec-butyl group, and a t-butyl group are preferred.

[0025] In formula (b) representing a moiety in general formula (1), R １１Specific examples of the linear alkoxy group having 1 to 8 carbon atoms or the branched alkoxy group having 3 to 8 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, an n-pentyloxy group, an iso-pentyloxy group, a neo-pentyloxy group, a t-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, etc. A linear or branched alkoxy group having 1 to 4 carbon atoms is preferred, and a linear alkoxy group having 1 to 4 carbon atoms is more preferred.

[0026] The compound represented by the above formula (1) can be synthesized by a conventional method described in, for example, JP-A-62-5941, JP-T-2017-518413, JP-A-58-196260, U.S. Patent Application Publication No. 2004 / 087692, etc.

[0027] In some embodiments, the anthraquinone compound represented by general formula (1) may include a compound represented by the following general formula (1a): １ and R ４ represents a cyano group, and R １ and R ４ the other represents a linear alkyl group having 1 to 12 carbon atoms, and R ２ , R ３ , R ５ , R ６ Each represents a hydrogen atom, and R ７ , R ８ and each independently represent a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a substituent represented by the following formula (a): In the following general formula (1a), １ is a cyano group, R ４ represents a linear alkyl group having 1 to 12 carbon atoms.

[0028] In the formula, R ４ represents a linear alkyl group having 1 to 12 carbon atoms; R ７ , R ８are each independently a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １０ When a plurality of groups are present, they may be the same or different.

[0029] Suitable specific examples of the compound represented by formula (1a) include, but are not limited to, the following:

[0030]

[0031]

[0032]

[0033]

[0034] In some embodiments, the anthraquinone compound represented by general formula (1) may include a compound represented by the following general formula (1b): １ and R ４ represents a cyano group, and R １ and R ４ the other represents a branched alkyl group having 3 to 12 carbon atoms, and R ２ , R ３ , R ５ , R ６ Each represents a hydrogen atom, and R ７ , R ８ and each independently represent a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a substituent represented by the following formula (a): In the following general formula (1b), １ is a cyano group, R ４ represents a branched alkyl group having 3 to 12 carbon atoms.

[0035] In the formula, R ４ represents a branched alkyl group having 3 to 12 carbon atoms; R ７ , R ８are each independently a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １０ When a plurality of groups are present, they may be the same or different.

[0036] Suitable specific examples of the compound represented by general formula (1b) include, but are not limited to, the following:

[0037]

[0038] In some embodiments, the anthraquinone compound represented by general formula (1) may include a compound represented by the following general formula (1c): １ and R ４ represents a cyano group, and R １ and R ４ the other is a hydrogen atom, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, or —CO ２ R ９ , -OCOR ９ , -COR ９ In the following general formula (1c), R in general formula (1) represents a cyano group or a trifluoromethyl group. １ is a cyano group, R ４ is a hydrogen atom, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group.

[0039] In the formula, R ４ represents a hydrogen atom, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR９ , -COR ９ , a cyano group, or a trifluoromethyl group. ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group. ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １０ When a plurality of R are present, they may be the same or different. ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R １１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms or a branched alkoxy group having 3 to 8 carbon atoms. １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １２ When a plurality of groups are present, they may be the same or different.

[0040] Suitable specific examples of the compound represented by general formula (1c) include, but are not limited to, the following:

[0041]

[0042]

[0043]

[0044] The anthraquinone compound represented by general formula (1c) can be synthesized, for example, based on the method described in U.S. Patent Application Publication No. 2004 / 087692. More specifically, the anthraquinone compound represented by general formula (1c) can be synthesized by reacting an anthraquinone compound represented by the following formula (m), synthesized by a conventional method described in JP-A-63-72760, with an iodobenzene derivative represented by the following formula (n), in the presence of a copper catalyst such as copper powder under basic conditions such as potassium carbonate, in a solvent such as N-methyl-2-pyrrolidone, at 140 to 160° C. Note that the compound represented by general formula (1cc) according to the modified embodiment described below can also be synthesized by a similar method.

[0045] In some modified embodiments, part or all of the anthraquinone compound represented by general formula (1) may be replaced with a compound represented by the following general formula (1cc): General formula (1cc) is a compound represented by the general formula (1c) in which R １ and R ４ a hydrogen atom of either one of the above, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , cyano group, or trifluoromethyl group is replaced by a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, and R ２ , R ３ , R ５ , R ６ This is the case except when all of the atoms are hydrogen atoms.

[0046] In the formula, R ４ represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms. ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group (where R ２ , R ３ , R ５ , R ６ (Except when all of R are hydrogen). ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １０ When a plurality of R are present, they may be the same or different. ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R １１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms or a branched alkoxy group having 3 to 8 carbon atoms. １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms. １２ When a plurality of groups are present, they may be the same or different.

[0047] In some embodiments, R in the above general formula (1cc) ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ The options and preferences that fit the definition of may be as described above for general formula (1). In another embodiment, in the compounds of general formula (1cc) above, R ４ is preferably a linear or branched alkyl group having 4 to 12 carbon atoms; R ７ , R ８ are each independently preferably a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, more preferably a linear alkoxy group or a branched alkoxy group having 4 to 12 carbon atoms; R ２ , R ３ , R ５ , R ６ At least one of R is a cyano group, and the other R ２ , R ３ , R ５ , R ６ is a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group, and R ２ and R ３ At least one of R is a cyano group, and the other R ２ , R ３ , R５ , R ６ is a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group, and R ２ and R ３ One of the R ２ , R ３ , R ５ , R ６ is a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group, and R ２ and R ３ is a cyano group positioned at the ortho position relative to the cyano group (—CN) shown in the general formula above, and the other R ２ , R ３ , R ５ , R ６ is a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group, and R ２ and R ３ is a cyano group positioned at the ortho position relative to the cyano group (—CN) shown in the general formula above, and the other R ２ , R ３ , R ５ , R ６ It is even more preferred that all of are hydrogen atoms.

[0048] Suitable specific examples of the compound represented by general formula (1cc) include, but are not limited to, the following:

[0049]

[0050] In some embodiments, the anthraquinone compound represented by general formula (1) may include a compound represented by the following general formula (1d): １ and R ４ each independently represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group, R ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group.

[0051] In the formula, R １ and R ４ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group; R ２ , R ３ , R ５ , R６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ or a trifluoromethyl group; R ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １０ When a plurality of R are present, they may be the same or different. ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R １１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; R １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １２ When a plurality of groups are present, they may be the same or different.

[0052] Specific examples of the compound represented by formula (1d) are not particularly limited, but include the following:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] The liquid crystal composition may contain only one of an anthraquinone compound represented by general formula (1a), an anthraquinone compound represented by general formula (1b), an anthraquinone compound represented by general formula (1c), and an anthraquinone compound represented by general formula (1d), or may contain a mixture of two or more of these compounds.

[0060] In the general formula (2), R in the formula of the anthraquinone compound represented by the general formula (1) １ and R ４ When one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms, １３ Specific examples of the branched alkyl group having 4 to 10 carbon atoms, which may be a linear alkyl group having 4 to 10 carbon atoms or a cyclic alkyl group having 4 to 10 carbon atoms, represented by the formula (I) are preferably an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, or an n-decyl group, and more preferably an n-heptyl group, an n-octyl group, an n-nonyl group, or an n-decyl group.

[0061] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms. １３Specific examples of the linear alkyl group having 1 to 12 carbon atoms or the branched alkyl group having 3 to 12 carbon atoms represented by R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neo-pentyl group, a t-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, a 2-ethylhexyl group, a 2-propylhexyl group, a 2-butylhexyl group, a 2-pentylhexyl group, and a 2-pentylheptyl group. １３ When R is a linear alkyl group, it preferably has 4 to 10 carbon atoms, and more preferably has 7 to 10 carbon atoms. １３ When represents a branched alkyl group, it preferably has 3 to 6 carbon atoms, and more preferably 3 or 4 carbon atoms.

[0062] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and the other is a linear alkyl group having 1 to 12 carbon atoms) １３ Specific examples of the linear alkoxy group having 1 to 12 carbon atoms or the branched alkoxy group having 3 to 12 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, an n-pentyloxy group, an iso-pentyloxy group, a neo-pentyloxy group, a t-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, an n-undecyloxy group, an n-dodecyloxy group, a 2-ethylhexyloxy group, a 2-propylhexyloxy group, a 2-butylhexyloxy group, a 2-pentylhexyloxy group, and a 2-pentylheptyloxy group. A straight or branched chain alkoxy group having 1 to 8 carbon atoms is preferred, a straight or branched chain alkoxy group having 5 to 8 carbon atoms is more preferred, and a straight chain alkoxy group having 5 to 8 carbon atoms is even more preferred.

[0063] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms. １３ As the alkyl group, a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms, or a linear alkoxy group having 1 to 10 carbon atoms or a branched alkoxy group having 3 to 10 carbon atoms is preferred, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms is more preferred, a linear alkyl group having 4 to 10 carbon atoms, a branched alkyl group having 3 or 4 carbon atoms, a linear alkoxy group having 5 to 8 carbon atoms, or a branched alkoxy group having 5 to 8 carbon atoms is even more preferred, and a linear alkyl group having 7 to 10 carbon atoms or a linear alkoxy group having 5 to 8 carbon atoms is even more preferred.

[0064] In the general formula (2), R in the formula of the anthraquinone compound represented by the general formula (1) １ and R ４ When one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms, １４ Specific examples of the linear alkyl group having 1 to 4 carbon atoms or the branched alkyl group having 3 or 4 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group. An n-propyl group, an n-butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a t-butyl group are preferred, and a t-butyl group is particularly preferred.

[0065] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms. １４Specific examples of the linear alkyl group having 1 to 8 carbon atoms or the branched alkyl group having 3 to 8 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neo-pentyl group, a t-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, and a 2-ethylhexyl group. A linear or branched alkyl group having 1 to 4 carbon atoms is preferred, and a branched alkyl group having 3 or 4 carbon atoms is more preferred.

[0066] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and the other is a linear alkyl group having 1 to 12 carbon atoms) １４ Specific examples of the linear alkoxy group having 1 to 8 carbon atoms or the branched alkoxy group having 3 to 8 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a t-butoxy group, an n-pentyloxy group, an iso-pentyloxy group, a neo-pentyloxy group, a t-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, and a 2-ethylhexyloxy group. A linear alkoxy group having 1 to 4 carbon atoms is more preferred.

[0067] In the general formula (2), (R in the formula in the anthraquinone compound represented by the general formula (1) １ and R ４ and the other is a linear alkyl group having 1 to 12 carbon atoms) １４ As the alkyl group, a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms is preferable, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms is more preferable, and a branched alkyl group having 3 or 4 carbon atoms is even more preferable.

[0068] Suitable specific examples of the compound represented by formula (2) include, but are not limited to, the following:

[0069]

[0070] The compound represented by the general formula (2) can be synthesized by a conventionally known method described, for example, in JP-A-62-5941, JP-T-2017-518413, JP-A-58-196260, etc.

[0071] The mass ratio of the anthraquinone compound represented by general formula (1) to the anthraquinone compound represented by general formula (2) contained in the liquid crystal composition is not particularly limited, but may be usually 10:1 to 1:10, preferably 5:1 to 1:5, and particularly preferably 2:1 to 1:2.

[0072] The total content of the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2) constituting the (A) dye compound in the liquid crystal composition is not particularly limited, but is usually 0.5 to 10 parts by mass, preferably 1 to 8 parts by mass, and more preferably 3 to 8 parts by mass, relative to 100 parts by mass of the liquid crystal material. When a dichroic dye (described below) other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2) constituting the (A) dye compound is used in combination in the liquid crystal composition, the total content (parts by mass relative to 100 parts by mass of the liquid crystal material) of the (A) dye compound and the dichroic dye other than the (A) dye compound is preferably in the above-mentioned range.

[0073] In an embodiment in which the anthraquinone compound represented by general formula (1) is represented by general formula (1a), the combination of the anthraquinone compounds represented by general formula (1a) and general formula (2) is not particularly limited. However, among the anthraquinone compounds represented by general formula (1a), R ４ is an alkyl group having 4 to 8 carbon atoms (Nos. 1 to 14), and anthraquinone compounds represented by general formula (2) (R １４ is an alkyl group having 1 to 4 carbon atoms, and R １３ is an alkyl group having 4 to 10 carbon atoms (Nos. 101 to 106).

[0074] In an embodiment in which the anthraquinone compound represented by general formula (1) is represented by general formula (1b), the combination of the anthraquinone compound represented by general formula (1b) and the anthraquinone compound represented by general formula (2) is not particularly limited. ４ is an alkyl group having 4 to 8 carbon atoms (Nos. 15 to 22), and among the anthraquinone compounds represented by general formula (2), R １３ is an alkyl group having 4 to 10 carbon atoms (Nos. 101 to 106 and 0108).

[0075] In an embodiment in which the anthraquinone compound represented by general formula (1) is represented by general formula (1c), the combination of the anthraquinone compound represented by general formula (1c) and the anthraquinone compound represented by general formula (2) is not particularly limited. ４ is an alkoxy group having 4 to 8 carbon atoms, a halogen atom, or —CO ２ R ９ (R ９ is as defined above) (Nos. 23, 25, 26, 29, 31, 32, 33, 34, 35, and 36), and anthraquinone compounds represented by general formula (2) in which R １３ is an alkyl group having 4 to 10 carbon atoms (Nos. 101 to 106 and 0108).

[0076] In an embodiment in which the anthraquinone compound represented by general formula (1) is represented by general formula (1d), the combination of the anthraquinone compound represented by general formula (1d) and the anthraquinone compound represented by general formula (2) is not particularly limited. １ and R ４ or both of which are alkyl groups having 4 to 8 carbon atoms (Nos. 39, 40, 41, 42, 48, 49, 51, 52, 57, 58, 59, 60, 65, 66, 67, 68, 70, 73, 74, 76, 77, 78, 79, 80, 81, 82, and 83), and anthraquinone compounds represented by general formula (2) in which R １３is an alkyl group having 4 to 10 carbon atoms (Nos. 101 to 106 and 0108).

[0077] The liquid crystal material (B) contained in the liquid crystal composition is not particularly limited as long as it is a material (compound having liquid crystal properties) having liquid crystallinity, such as nematic liquid crystal, cholesteric liquid crystal, or smectic liquid crystal. Examples of compounds having liquid crystallinity include the liquid crystal compounds described on pages 154 to 192 and 715 to 722 of "Liquid Crystal Device Handbook" (edited by Committee 142 of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, Ltd., 1989). Specific examples of such liquid crystal compounds include Schiff base compounds, azoxy compounds, biphenyl compounds, phenylcyclohexane compounds, ester compounds, terphenyl compounds, biphenylcyclohexane compounds, pyrimidine compounds, dioxane compounds, bicyclooctane compounds, and cubane compounds.

[0078] The liquid crystal composition may contain a dichroic dye other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2), an optically active substance that exhibits or does not exhibit a liquid crystal phase, such as cholesteryl nonanoate, various additives such as an ultraviolet absorber and an antioxidant, a photocurable compound, a photopolymerization initiator, and the like.

[0079] In order to adjust the performance of the light-adjusting element, such as contrast, light resistance, and hue, a dichroic dye other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2) may be used in combination with the liquid crystal composition. The dichroic dye that can be used in combination is not particularly limited, and may be selected from, for example, azo dyes, anthraquinone dyes, perylene dyes, quinophthalone dyes, merocyanine dyes, azomethine dyes, phthaloperylene dyes, indigo dyes, azulene dyes, dioxazine dyes, polythiophene dyes, and the like. Specific examples include those described in "Dichroic Dyes for Liquid Crystal Displays" (A.V. Ivashchenko, CRC, 1994). Among these, it is preferable to use an azo dye, an anthraquinone dye, a perylene dye, or a quinophthalone dye in combination, it is more preferable to use an azo dye or an anthraquinone dye in combination, and it is even more preferable to use an anthraquinone dye in combination.

[0080] Suitable specific examples of the dichroic dye other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2) are not particularly limited, but include compounds (anthraquinone dyes) represented by the following general formulas (3-1) to (3-3).

[0081]

[0082] R in formula (3-1) １５ is, but is not particularly limited to, a linear or branched alkyl group having 4 to 7 carbon atoms, or a substituent represented by the following formula (d):

[0083]

[0084] (In formula (d), R ２１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms.

[0085] R in formula (3-2) １６ and R １７are not particularly limited, but each independently preferably represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms, a linear or branched alkoxy group having 4 to 8 carbon atoms (which may be interrupted by an aryl ring), a linear or branched fatty acid ester group having 6 to 18 carbon atoms, or a substituent represented by the above formula (d).

[0086] R in formula (3-3) １８ is not particularly limited, but is preferably a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms.

[0087] R １９ and R ２０ are not particularly limited, but each independently represents a hydrogen atom or a group represented by the following formula (e):

[0088]

[0089] (In formula (e), R ２２ represents a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms or a branched alkoxy group having 3 to 8 carbon atoms. １９ and R ２０ It is more preferable that one of the groups is a hydrogen atom and the other is a substituent represented by the above formula (e).

[0090] Suitable, non-limiting specific examples of anthraquinone dyes that can be used as dichroic dyes other than the anthraquinone compounds represented by general formula (1) and the anthraquinone compounds represented by general formula (2) are shown in Tables 1 to 4 below.

[0091]

[0092]

[0093]

[0094]

[0095] Suitable, non-limiting examples of azo dyes used as dichroic dyes other than the anthraquinone compounds represented by general formula (1) and the anthraquinone compounds represented by general formula (2) include compounds represented by the following general formula (4).

[0096]

[0097] A １ is, but is not limited to, a hydrogen atom, —CO ２ A ３ , a linear or branched alkyl group having 4 to 8 carbon atoms, and a substituent represented by the following formula (f), (g), or (h):

[0098]

[0099] (In formula (f), A ４ represents a linear alkoxy group having 1 to 8 carbon atoms or a branched alkoxy group having 3 to 8 carbon atoms. ５ represents a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms. ３ is preferably a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms.

[0100] A ２ is a substituent represented by, but not limited to, the following formula (i), (j) or (k):

[0101]

[0102] (In formula (i), A ６ represents a linear alkyl group having 1 to 8 carbon atoms. ７ and A ８ each independently represents a 1,4-phenylene group or a 1,4-naphthalenediyl group; A ９ represents a linear alkoxy group having 1 to 8 carbon atoms; L １ represents -N=N- or -N=CH-, and L ２ represents —O— or —O—CO—.) is preferred.

[0103] Suitable, non-limiting specific examples of azo dyes that can be used as dichroic dyes other than the anthraquinone compounds represented by general formula (1) and the anthraquinone compounds represented by general formula (2) are shown in Tables 5 and 6 below.

[0104]

[0105]

[0106] When a dichroic dye other than the anthraquinone compound represented by general formula (1) and the anthraquinone compound represented by general formula (2) is used in combination, the content of the compounds represented by general formula (1) and general formula (2) in the total dichroic dye is not particularly limited, but is preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more.

[0107] The liquid crystal composition may further optionally contain light stabilizers such as benzotriazoles, benzophenones, and hindered amines, antioxidants such as phosphites and hindered phenols, thermal polymerization inhibitors, thiol compounds, photosensitizers, photosensitizers, chain transfer inhibitors, polymerization inhibitors, adhesion promoters, antifoaming agents, crosslinking agents, surfactants, thermal curing accelerators, thermoplastic resins, thermosetting resins, thickeners such as urethane diacrylate, etc. Furthermore, to control the cell gap as a light-adjusting element, spherical or cylindrical spacers such as silica, glass, plastic, or ceramic may be added to the liquid crystal composition. The cell gap in the light-adjusting element can be set in the range of 2 to 100 μm.

[0108] For example, a photocurable compound and a photopolymerization initiator can be contained in a liquid crystal composition, as exemplified in Patent Document 4. By photocuring a liquid crystal composition containing these components, the polymer and the liquid crystal substance are phase-separated, and a film having a light-controlling layer or the like can be obtained.

[0109] In this case, the photocurable compound having a functional group polymerizable by the action of a photopolymerization initiator is not particularly limited, but examples thereof include compounds having a (meth)acrylate group, compounds having a vinyl group, and compounds having an allyl group. Compounds having a (meth)acrylate group are preferred. The photocurable compound may be used alone or as a mixture of two or more types. It is more preferable to use both a mono(meth)acrylate compound having one (meth)acrylate group in one molecule and a di(meth)acrylate compound having two (meth)acrylate groups in one molecule in combination. In this specification, the term "(meth)acrylate" means "methacrylate and / or acrylate."

[0110] The mono(meth)acrylate compound is preferably a mono(meth)acrylate having a linear or branched alkyl group having 5 to 13 carbon atoms. Specific examples thereof include linear alkyl mono(meth)acrylates such as pentyl(meth)acrylate, hexyl(meth)acrylate, heptyl(meth)acrylate, octyl(meth)acrylate, nonyl(meth)acrylate, decyl(meth)acrylate, undecyl(meth)acrylate, dodecyl(meth)acrylate, and tridecyl(meth)acrylate, and branched alkyl mono(meth)acrylates such as 2-methylhexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, 2-propylhexyl(meth)acrylate, 2-methylheptyl(meth)acrylate, 2-ethylheptyl(meth)acrylate, and 2-propylheptyl(meth)acrylate.

[0111] Suitable examples of the di(meth)acrylate compound include 1,4-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,11-undecanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, and 1,13-tridecanediol di(meth)acrylate.

[0112] The photopolymerization initiator that may be contained in the liquid crystal composition is not particularly limited as long as it is a compound that can polymerize a photocurable compound by irradiation with light. A photopolymerization initiator that does not remain in the cured liquid crystal composition after irradiation with light and cause deterioration of dichroic dyes or the like is preferred. One type of photopolymerization initiator may be used alone, or two or more types may be used as a mixture. Preferred examples of the photopolymerization initiator include alkylphenone-based photopolymerization initiators such as Darocur 1173, Irgacure 651, and Irgacure 184, and phosphine oxide-based photopolymerization initiators such as Irgacure TPO.

[0113] The light-adjusting element comprises a pair of substrates, at least one of which is a transparent substrate having a transparent electrode, and a layer of the liquid crystal composition according to any of the above embodiments or a photocured product thereof sandwiched between them. Examples of the substrate include inorganic transparent materials such as glass and quartz, and colorless, transparent, or opaque materials such as metals, metal oxides, semiconductors, ceramics, plastic plates, and plastic films. The electrodes are formed on the substrate by applying a thin film of, for example, a metal oxide, metal, semiconductor, or organic conductive material to the entire surface or a portion of the substrate using a known coating method, printing method, or vapor deposition method such as sputtering. In particular, to obtain a large-area light-adjusting element, it is desirable to use an electrode substrate in which an ITO (indium oxide, tin oxide) electrode is formed on a transparent polymer film such as PET using a vapor deposition method such as sputtering or a printing method, from the standpoints of productivity and processability. Wiring may be provided on the substrate to connect the electrodes or the electrodes to the outside. For example, the substrate may be a segment-drive electrode substrate, a matrix-drive electrode substrate, or an active-matrix drive electrode substrate. Furthermore, the electrode surface provided on the substrate is covered with an organic compound such as polyimide, polyamide, silicon, or cyanide, or SiO ２ , TiO ２ , ZrO ２ The entire surface or a part of the surface may be covered with a protective film or an alignment film made of an inorganic compound such as those mentioned above, or a mixture thereof.

[0114] The use of a plastic film as a substrate allows for a flexible and lightweight light-adjusting element to be obtained. Therefore, the light-adjusting element can be sandwiched between a pair of flat or curved glass or hard plastic substrates via an adhesive layer such as polyvinyl butyral, vinyl acetate ester, double-sided tape, or adhesive. Alternatively, the light-adjusting element can be attached to the surface of a single flat or curved glass or hard plastic substrate using double-sided tape or adhesive. The light-adjusting element can also be sandwiched between soft plastic substrates or attached to one or both sides. A protective layer such as a hard coat, an ultraviolet-blocking layer, an infrared-blocking layer, or a half mirror may be provided on the substrate surface opposite the electrode surface of the light-adjusting element, or a color filter or polarizer filter may be laminated thereon. An electroluminescent display element, a light-emitting diode display element, an electrochromic display element, or another liquid crystal display element may also be laminated on the light-adjusting element.

[0115] The driving device for applying a voltage to the light-adjusting element is a device that can apply a DC voltage or an AC voltage and that opens or shorts the electrodes when no voltage is applied. The driving device may also be equipped with a voltage application circuit for segment driving, a voltage application circuit for matrix driving, a voltage application circuit for active matrix driving, etc.

[0116] Such a light-adjusting element has a neutral color, little color leakage in the visible light range, and excellent contrast, and is therefore ideal for use in vehicles or as a building material.

[0117] The present invention will be described in more detail below with reference to examples, but these are illustrative and do not limit the present invention in any way. In the text, "parts" and "%" are by mass unless otherwise specified. The maximum absorption wavelength in the examples is a value measured using a spectrophotometer "UV-3150" manufactured by Shimadzu Corporation.

[0118] (I) Examples Using Compounds Represented by General Formula (1a) and Comparative Examples Thereof Example 1 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as the (B) liquid crystal material, and 0.0120 parts of the compound represented by No. 2 and 0.0180 parts of the compound represented by No. 101 as the (A) dye compound were stirred for 1 hour while being heated on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0119] Example 2 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 1, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 215 as (A) dye compounds, were stirred for 1 hour while heating on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0120] Example 3 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 2, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 220 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0121] Example 4 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0122 parts of the compound represented by No. 2, 0.0147 parts of the compound represented by No. 102, and 0.0031 parts of the compound represented by No. 202 as (A) dye compounds, were stirred for 1 hour while heating on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0122] Example 5 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 2, 0.0147 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 220 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0123] Example 6 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 10, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were stirred for 1 hour while heating on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0124] Comparative Example 1 (Preparation of Comparative Liquid Crystal Composition) A comparative liquid crystal composition (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass) was prepared in the same manner as in Example 1, except that the (A) dye compound was changed to 0.0104 parts of a compound represented by the following formula (X) disclosed in WO2022 / 138440, 0.0147 parts of a compound represented by the following formula (Y) disclosed in WO2022 / 158493, and 0.0049 parts of the above compound represented by No. 213.

[0125]

[0126] Comparative Example 2 (Preparation of Comparative Liquid Crystal Composition) A comparative liquid crystal composition (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass) was prepared in the same manner as in Example 1, except that the (A) dye compound was changed to 0.0104 parts of a compound represented by the following formula (Z) disclosed in JP-B 03-063489, 0.0147 parts of a compound represented by the above formula (Y) disclosed in WO 2022 / 158493, and 0.0049 parts of the above compound represented by No. 213.

[0127]

[0128] Example 7 (Preparation of light-adjusting element of the present invention) The liquid crystal composition obtained in Example 1 was sealed in an element having a transparent electrode and two glass substrates, upper and lower, which had been subjected to a homogeneous alignment treatment by rubbing a polyamide resin on the surface in contact with the liquid crystal, with a gap of 15 μm between the substrates, to obtain a light-adjusting element. In the light-adjusting element, when no voltage was applied, the liquid crystal was in a homogeneous alignment state, and the dye molecules were also in a similar alignment state according to the liquid crystal.

[0129] Examples 8 to 12 (Preparation of light-controlling elements of the present invention) Light-controlling elements of the present invention were prepared in the same manner as in Example 7, except that the liquid crystal compositions obtained in Examples 2 to 6 were used instead of the liquid crystal composition obtained in Example 1.

[0130] Comparative Examples 3 and 4 (Preparation of Comparative Light-Controlling Devices) Comparative light-controlling devices were prepared in the same manner as in Example 7, except that the liquid crystal compositions obtained in Comparative Examples 1 and 2 were used instead of the liquid crystal composition obtained in Example 1.

[0131] [Method for measuring and evaluating physical properties of light-adjusting elements] The physical properties of the light-adjusting elements obtained in Examples 7 to 12 and Comparative Examples 3 and 4 were measured and evaluated as follows.

[0132] (Measurement of Transmittance of Light-Adjusting Element) For the light-adjusting elements obtained in Examples 7 to 12 and Comparative Example 4, the transmittance (Kz) for linearly polarized light parallel to the orientation direction and the transmittance (Ky) for polarized light perpendicular to the orientation direction were measured using a spectrophotometer "U-4100" manufactured by Hitachi, Ltd. The measurements were carried out over a wavelength range of 400 to 700 nm.

[0133] (Kz(Y) after luminosity correction, Ky(Y) after luminosity correction) For the photochromic elements obtained in Examples 7 to 12 and Comparative Example 4, the transmittance Kz for linearly polarized light parallel to the alignment direction, corrected for luminosity, Kz(Y) (%), and the transmittance Ky for polarized light perpendicular to the alignment direction, corrected for luminosity, Ky(Y) (%), were determined. The luminosity-corrected Kz(Y) (%) and luminosity-corrected Ky(Y) (%) are transmittances corrected to luminosity according to JIS Z 8722:2009 for Kz and Ky at each wavelength determined at predetermined wavelength intervals dλ (here, 5 nm) in the wavelength range of 400 to 700 nm. Specifically, the Kz and Ky at each wavelength were substituted into the following formulas (I) and (II), respectively, to calculate the Kz and Ky. In the following formulas (I) and (II), Pλ represents the spectral distribution of standard light (light source C), and yλ represents the 2-degree visual field color matching function.

[0134]

[0135] (Calculation of Dichroic Ratio of Light-Adjusting Device) For the light-adjusting devices obtained in Examples 7 to 12 and Comparative Example 4, the dichroic ratio after luminosity correction in the range of 400 to 700 nm was calculated by calculating the absorbance ratio from the transmittance Kz (Y) (%) for linearly polarized light parallel to the alignment direction, which was corrected for luminosity, and the transmittance Ky (Y) (%) for polarized light perpendicular to the alignment direction, which was corrected for luminosity, according to the following formula (III): The results are shown in Table 7.

[0136]

[0137]

[0138] As shown in Table 7, it was confirmed that the light control elements of Examples 7 to 12 exhibited better dichroic ratios than the light control element of Comparative Example 4.

[0139] (Light Resistance Test of Light Control Device) A UV cut filter of 400 nm or less was attached to the light control devices obtained in Examples 7 to 12 and Comparative Example 3, and the devices were subjected to light resistance test at an illuminance of 650 W / m under a condition of 63°C. ２ The light resistance test was carried out by irradiating the light-adjusting element with a metal halide lamp of 1000 V for 300 hours. The transmittance of the light-adjusting element in the range of 380 to 780 nm was measured with a spectrophotometer before and after the light resistance test, both when no voltage was applied and when a voltage (48 V) was applied. From the obtained transmission spectrum, chromaticity (L ＊ , a ＊ , b ＊ ) was calculated, and the color difference (ΔE ａｂ ) was calculated by the following calculation formula (iv): ａｂ The smaller the value of ΔE, the smaller the color change before and after the light resistance test, and the more excellent the light resistance. The results are shown in Table 8. ａｂ (L ＊ , a ＊ , b ＊ ) = {(ΔL ＊ ) ２ + (Δa ＊ ) ２ + (Δb ＊ ) ２} １／２ (iv)

[0140]

[0141] As shown in Table 8, the light control elements of Examples 7 to 12 had a lower ΔE than the light control element of Comparative Example 3 both when a voltage was applied and when no voltage was applied. ａｂ It was confirmed that the light resistance was small and excellent.

[0142] (Hue a when voltage is applied to the dimming element ＊ value, b ＊ For the light-adjustable elements obtained in Examples 7 to 12 and Comparative Examples 3 and 4, the transmittance was measured using a spectrophotometer, and the hue a was calculated in accordance with JIS Z 8781-4:2013.＊ value, b ＊ The values ​​are shown in Table 9.

[0143]

[0144] As shown in Table 9, the dimming elements of Examples 7 to 12 ＊ value, b ＊ It was therefore confirmed that the light-controlling elements of Examples 7 to 12 exhibited significantly improved performance compared to the light-controlling elements of Comparative Examples 3 and 4 in that they were excellent in all of the properties of dichroism, light fastness, and achromatic color in a well-balanced manner.

[0145] (II) Examples Using Compounds Represented by General Formula (1b) and Comparative Examples Thereof Example 13 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, and 0.0120 parts of the compound represented by No. 15 and 0.0180 parts of the compound represented by No. 101 as (A) dye compounds, were stirred for 1 hour while being heated on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0146] Example 14 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 15, 0.0147 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 202 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0147] Example 15 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 21, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0148] Comparative Example 5 (Preparation of Comparative Liquid Crystal Composition) A comparative liquid crystal composition (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass) was prepared in the same manner as in Example 13, except that the (A) dye compound was changed to 0.0104 parts of the compound represented by formula (X) disclosed in WO 2022 / 138440, 0.0147 parts of the compound represented by formula (Y) disclosed in WO 2022 / 158493, and 0.0049 parts of the compound represented by No. 215.

[0149] Comparative Example 6 (Preparation of Comparative Liquid Crystal Composition) A comparative liquid crystal composition (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass) was prepared in the same manner as in Example 13, except that the (A) dye compound was changed to 0.0104 parts of the compound represented by formula (Z) disclosed in JP-B 03-063489, 0.0147 parts of the compound represented by formula (Y) disclosed in WO 2022 / 158493, and 0.0049 parts of the compound represented by No. 215.

[0150] The liquid crystal composition obtained in Example 13 was sealed in a device having a transparent electrode and two glass substrates, one above the other, which had been subjected to a homogeneous alignment treatment by rubbing a polyamide resin on the surface in contact with the liquid crystal, with a gap of 15 μm between the substrates, to obtain a light-control device. In the light-control device, when no voltage was applied, the liquid crystal was in a homogeneous alignment state, and the dye molecules were also in a similar alignment state according to the liquid crystal.

[0151] Examples 17 and 18 (Preparation of light-controlling elements of the present invention) Light-controlling elements of the present invention were prepared in the same manner as in Example 16, except that the liquid crystal compositions obtained in Examples 14 and 15 were used instead of the liquid crystal composition obtained in Example 13.

[0152] Comparative Examples 7 and 8 (Preparation of Comparative Light-Controlling Elements) Comparative light-controlling elements were prepared in the same manner as in Example 16, except that the liquid crystal compositions obtained in Comparative Examples 5 and 6 were used instead of the liquid crystal composition obtained in Example 13.

[0153] [Methods for measuring and evaluating physical properties of light-adjusting elements] For the light-adjusting elements obtained in Examples 16 to 18 and Comparative Examples 7 and 8, the dichroic ratio was measured and calculated, the color difference was measured and calculated in a light resistance test, and the hue a ＊ value, b ＊ The values ​​were measured and calculated as described above for Example (I) above, and the results are shown in the table below.

[0154]

[0155] As shown in Table 10, it was confirmed that the light control elements of Examples 16 to 18 exhibited better dichroic ratios than the light control element of Comparative Example 8.

[0156]

[0157] As shown in Table 11, the light control elements of Examples 16 to 18 had a larger ΔE than the light control element of Comparative Example 7 both when a voltage was applied and when no voltage was applied. ａｂ It was confirmed that the light resistance was small and excellent.

[0158]

[0159] As shown in Table 12, the dimming elements of Examples 16 to 18 ＊ value, b ＊ It was therefore confirmed that the light-controlling elements of Examples 16 to 18 exhibited significantly improved performance compared to the light-controlling elements of Comparative Examples 7 and 8 in that they were excellent in all of the properties of dichroism, light fastness, and achromatic color in a well-balanced manner.

[0160] (III) Examples Using a Compound Represented by General Formula (1c) Synthesis Example 1 (Synthesis of Anthraquinone Compound Represented by No. 23 of the Above Specific Example) 0.9 parts of a compound represented by the following formula (5A), 0.02 parts of copper powder, 0.02 parts of copper iodide, 2.0 parts of 1-fluoro-4-iodobenzene, 0.02 parts of potassium carbonate, and 0.15 parts of sodium acetate were added to 20 parts of NMP and stirred at 140 to 150°C for 12 hours. The reaction solution was then cooled to 25°C, and 200 parts of methanol was added, followed by further stirring for 1 hour. The reaction product was collected by filtration, washed with methanol, and then dried in a hot air dryer at 50°C for 24 hours. The resulting crude product was dissolved in toluene and subjected to column purification using toluene as a developing solvent. The solvent was distilled off from the purified solution under reduced pressure, and the residue was dried in a hot air dryer at 50°C for 24 hours, yielding 0.2 parts of the above compound represented by No. 23 as a dark brown solid. The maximum absorption wavelength of this compound in toluene was 651 nm.

[0161]

[0162] Synthesis Example 2 (Synthesis of Anthraquinone Compound Represented by No. 34 of the Specific Example Above) 0.9 parts of the compound represented by formula (5A) above, 0.02 parts of copper powder, 0.02 parts of copper iodide, 2.0 parts of 4-butoxy-1-iodobenzene, 0.02 parts of potassium carbonate, and 0.15 parts of sodium acetate were added to 20 parts of NMP and stirred at 140 to 150°C for 12 hours. The reaction solution was then cooled to 25°C, and 200 parts of methanol was added, followed by further stirring for 1 hour. The reaction product was collected by filtration, washed with methanol, and then dried in a hot air dryer at 50°C for 24 hours. The resulting crude product was dissolved in toluene and subjected to column purification using toluene as a developing solvent. The solvent was distilled off from the purified solution under reduced pressure, and the residue was dried in a hot air dryer at 50°C for 24 hours, yielding 0.2 parts of the compound represented by No. 34 as a dark brown solid. The maximum absorption wavelength of this compound in toluene was 651 nm.

[0163] Synthesis Example 3 (Synthesis of Anthraquinone Compound Represented by No. 36 of the Specific Example Above) 0.9 parts of the compound represented by formula (5A) above, 0.02 parts of copper powder, 0.02 parts of copper iodide, 2.2 parts of ethyl 4-iodo-1-benzoate, 0.02 parts of potassium carbonate, and 0.15 parts of sodium acetate were added to 20 parts of NMP and stirred at 140 to 150°C for 12 hours. The reaction solution was then cooled to 25°C, and 200 parts of methanol was added, followed by further stirring for 1 hour. The reaction product was collected by filtration, washed with methanol, and then dried in a hot air dryer at 50°C for 24 hours. The resulting crude product was dissolved in toluene and subjected to column purification using toluene as a developing solvent. The solvent was distilled off from the purified solution under reduced pressure, and the residue was dried in a hot air dryer at 50°C for 24 hours, yielding 0.2 parts of the compound represented by No. 36 as a dark brown solid. The maximum absorption wavelength of this compound in toluene was 654 nm.

[0164] Example 19 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, and 0.0120 parts of the compound represented by No. 23 and 0.0180 parts of the compound represented by No. 101 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0165] Example 20 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 23, 0.0147 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 202 as (A) dye compounds, were stirred for 1 hour while heating on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0166] Example 21 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 34, 0.0147 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 220 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0167] Example 22 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 36, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0168] The liquid crystal composition obtained in Example 19 was sealed in a device having a transparent electrode and two glass substrates, one above the other, which had been subjected to a homogeneous alignment treatment by rubbing a polyamide resin on the surface in contact with the liquid crystal, with a gap of 15 μm between the substrates, to obtain a light-control device. In the light-control device, when no voltage was applied, the liquid crystal was in a homogeneous alignment state, and the dye molecules were also in a similar alignment state according to the liquid crystal.

[0169] Examples 24 to 26 (Preparation of light-controlling elements of the present invention) Light-controlling elements of the present invention were prepared in the same manner as in Example 23, except that the liquid crystal compositions obtained in Examples 20 to 22 were used instead of the liquid crystal composition obtained in Example 19.

[0170] [Methods for measuring and evaluating physical properties of light-adjusting elements] For the light-adjusting elements obtained in Examples 23 to 26, the dichroic ratio was measured and calculated, the color difference was measured and calculated in a light resistance test, and the hue a ＊ value, b ＊ The values ​​were measured and calculated in the same manner as described above for Example (I). The results are shown in the following tables. To facilitate understanding of the advantageous effects of the present invention, the results obtained for Comparative Example 7 and / or Comparative Example 8 are also shown in each of Tables 13 to 15.

[0171]

[0172] As shown in Table 13, it was confirmed that the light control elements of Examples 23 to 26 exhibited better dichroic ratios than the light control element of Comparative Example 8.

[0173]

[0174] As shown in Table 14, the light control elements of Examples 23 to 26 had a lower ΔE than the light control element of Comparative Example 7 both when a voltage was applied and when no voltage was applied. ａｂ It was confirmed that the light resistance was small and excellent.

[0175]

[0176] As shown in Table 15, the dimming elements of Examples 23 to 26 ＊ value, b ＊It was therefore confirmed that the light-controlling elements of Examples 23 to 26 exhibited significantly improved performance compared to the light-controlling elements of Comparative Examples 7 and 8 in that they were excellent in all of the properties of dichroism, light fastness, and achromatic color in a well-balanced manner.

[0177] (III-i) Reference Example Synthesis Example 4 Using a Compound Represented by General Formula (1cc) (Synthesis of Anthraquinone Compound Represented by No. 1R in the Above Specific Example) 0.9 parts of a compound represented by the following formula (6A), 0.02 parts of copper powder, 0.02 parts of copper iodide, 2.4 parts of 1-heptyl-4-iodobenzene, 0.02 parts of potassium carbonate, and 0.15 parts of sodium acetate were added to 20 parts of NMP and stirred at 140 to 150°C for 12 hours. The reaction solution was then cooled to 25°C, and 200 parts of methanol was added, followed by further stirring for 1 hour. The reaction product was collected by filtration, washed with methanol, and then dried in a hot air dryer at 50°C for 24 hours. The resulting crude product was dissolved in toluene and subjected to column purification using toluene as a developing solvent. The solvent was distilled off under reduced pressure from the purified solution, and the residue was dried in a hot air dryer at 50°C for 24 hours, yielding 0.2 parts of the above compound represented by No. 1R as a dark brown solid. The maximum absorption wavelength of this compound in toluene was 646 nm.

[0178]

[0179] Reference Example 1 (Preparation of Reference Liquid Crystal Composition) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, and 0.0104 parts of the compound represented by No. 1R, 0.0147 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a reference liquid crystal composition (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0180] The liquid crystal composition obtained in Reference Example 1 was sealed in an element having a transparent electrode and two glass substrates, one above the other, which had been subjected to a homogeneous alignment treatment by rubbing a polyamide resin on the surface in contact with the liquid crystal, with a gap of 15 μm between the substrates, to obtain a light-adjusting element. In the light-adjusting element, when no voltage was applied, the liquid crystal was in a homogeneous alignment state, and the dye molecules were also in a similar alignment state according to the liquid crystal.

[0181] [Methods for measuring and evaluating physical properties of light-adjusting element] For the light-adjusting element obtained in Reference Example 2, the dichroic ratio was measured and calculated, the color difference was measured and calculated in a light resistance test, and the hue a ＊ value, b ＊ The dichroic ratio of the light-adjusting element obtained in Reference Example 2 was 12.7, and the color difference ΔEab when no voltage was applied and the color difference ΔEab when a voltage was applied were 0.6 and 0.6, respectively, in a light resistance test. ＊ value and b ＊ The values ​​were −3.0 and 3.2 (both less than 5), respectively. Thus, it was found that the light control device of Reference Example 2 exhibited a good dichroic ratio, excellent light fastness, and achromatic color. That is, it was confirmed that the light control device of Reference Example 2 exhibited significantly improved performance in that it had a well-balanced and excellent overall property of dichroism, light fastness, and achromatic color compared to light control devices according to conventional techniques, such as the light control devices of Comparative Examples 7 and 8.

[0182] (IV) Example Using Compound Represented by General Formula (1d) Example 27 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as the (B) liquid crystal material, and 0.012 parts of the compound represented by No. 39 and 0.018 parts of the compound represented by No. 101 as the (A) dye compound were stirred for 1 hour while being heated on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0183] Example 28 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 39, 0.0147 parts of the compound represented by No. 102 as (A) dye compounds, and 0.0049 parts of the compound represented by No. 202 were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0184] Example 29 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0104 parts of the compound represented by No. 42, 0.0147 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 215 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0185] Example 30 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0140 parts of the compound represented by No. 39, 0.0138 parts of the compound represented by No. 102, and 0.0022 parts of the compound represented by No. 220 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0186] Example 31 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0140 parts of the compound represented by No. 41, 0.0138 parts of the compound represented by No. 102, and 0.0049 parts of the compound represented by No. 220 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0187] Example 32 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0140 parts of the compound represented by No. 76, 0.0138 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were stirred for 1 hour while heating on a hot plate at 70°C to prepare a liquid crystal composition of the present invention (the content of the (A) dye compound relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0188] Example 33 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4"-n-pentylterphenyl as (B) liquid crystal materials, 0.0140 parts of the compound represented by No. 79, 0.0138 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0189] Example 34 (Preparation of Liquid Crystal Composition of the Present Invention) 0.51 parts of 1-cyano-4'-n-pentylbiphenyl, 0.25 parts of 1-cyano-4'-n-heptylbiphenyl, 0.16 parts of 1-cyano-4'-n-octyloxybiphenyl, and 0.08 parts of 1-cyano-4''-n-pentylterphenyl as (B) liquid crystal materials, 0.0140 parts of the compound represented by No. 51, 0.0138 parts of the compound represented by No. 101, and 0.0049 parts of the compound represented by No. 213 as (A) dye compounds, were heated on a hot plate at 70°C and stirred for 1 hour to prepare a liquid crystal composition of the present invention (the content of the (A) dye compounds relative to the total amount of the (B) liquid crystal material was approximately 3.0% by mass).

[0190] The liquid crystal composition obtained in Example 27 was sealed in a device having a transparent electrode and two glass substrates, one on top of the other, which had been subjected to a homogeneous alignment treatment by rubbing a polyamide resin on the surface in contact with the liquid crystal, with a gap of 15 μm between the substrates, to obtain a light-controlling device. In the light-controlling device, when no voltage was applied, the liquid crystal was in a homogeneous alignment state, and the dye molecules were also in a similar alignment state according to the liquid crystal.

[0191] Examples 36 to 42 (Preparation of light-controlling elements of the present invention) Light-controlling elements of the present invention were prepared in the same manner as in Example 35, except that the liquid crystal compositions obtained in Examples 28 to 34 were used instead of the liquid crystal composition obtained in Example 27.

[0192] [Methods for measuring and evaluating physical properties of light-adjusting elements] For the light-adjusting elements obtained in Examples 35 to 42, the dichroic ratio was measured and calculated, the color difference was measured and calculated in a light resistance test, and the hue a ＊ value, b ＊ The values ​​were measured and calculated in the same manner as described above for Example (I). The results are shown in the following tables. To facilitate understanding of the advantageous effects of the present invention, the results obtained for Comparative Example 3 and / or Comparative Example 4 are also shown in each of Tables 16 to 18.

[0193]

[0194] As shown in Table 16, it was confirmed that the light control elements of Examples 35 to 42 exhibited better dichroic ratios than the light control element of Comparative Example 4.

[0195]

[0196] As shown in Table 17, the light control elements of Examples 35 to 42 had a lower ΔE than the light control element of Comparative Example 3 both when a voltage was applied and when no voltage was applied. ａｂ It was confirmed that the light resistance was small and excellent.

[0197]

[0198] As shown in Table 18, the dimming elements of Examples 35 to 42 ＊ value, b ＊ It was therefore confirmed that the light-controlling elements of Examples 35 to 42 exhibited significantly improved performance compared to the light-controlling elements of Comparative Examples 3 and 4 in that they were excellent in all of the properties of dichroism, light fastness, and achromatic color in a well-balanced manner.

[0199] By using the liquid crystal composition of the present invention, a light-controlling liquid crystal device having a high dichroic ratio, an achromatic color, and excellent light resistance can be obtained. Such a light-controlling device can be suitably used for outdoor building materials and vehicle applications, which require high durability, a dichroic ratio, and designability.

Claims

1. A liquid crystal composition containing (A) a dye compound and (B) a liquid crystal material, wherein the dye compound (A) is represented by the following general formula (1): (In the formula, R １ and R ４ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a halogen atom, -CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group; R ２ , R ３ , R ５ , R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a branched alkoxy group having 3 to 4 carbon atoms, a halogen atom, —CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, provided that R １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ２ , R ３ , R ５ , R ６ each represents a hydrogen atom; R ７ , R ８ are each independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, or a group represented by the following formula (a): (In formula (a), R １０ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １０ When a plurality of R are present, they may be the same or different. １ and R ４ When either one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, R ７ , R ８ each independently represents a hydrogen atom, a linear alkoxy group having 4 to 10 carbon atoms, or a substituent represented by the above formula (a); R ９ each independently represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, (In formula (b), R １１ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; R １１ When a plurality of groups are present, they may be the same or different. (In formula (c), R １２ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms; R １２ (ii) an anthraquinone compound represented by the following general formula (2): (In the formula, R １３ represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, or a linear alkoxy group having 1 to 12 carbon atoms, or a branched alkoxy group having 3 to 12 carbon atoms; R １４ represents a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms, or a branched alkoxy group having 3 to 8 carbon atoms; provided that R １ and R ４ When one of R is a cyano group and the other is a linear alkyl group having 1 to 12 carbon atoms, R １３ represents a hydrogen atom or a branched alkyl group having 4 to 10 carbon atoms, which may be a linear alkyl group having 4 to 10 carbon atoms or a cyclic alkyl group having 4 to 10 carbon atoms; R １４ represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 4 carbon atoms.

2. R in Equation (1) １ and R ４ each independently represents a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms, a linear alkoxy group having 1 to 12 carbon atoms or a branched alkoxy group having 3 to 12 carbon atoms, a fluorine atom, a chlorine atom, -CO ２ R ９ , -OCOR ９ , -COR ９ , a cyano group, or a trifluoromethyl group, and R ２ , R ３ , R ５ and R ６ each independently represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms, a fluorine atom, a chlorine atom, or —CO ２ R ９ , -COR ９ , a cyano group, or a trifluoromethyl group, and R ９ 2. A liquid crystal composition comprising the anthraquinone compound according to claim 1, wherein each of the groups independently represents a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms.

3. R ​​in Equation (2) １３ is a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a linear alkoxy group having 1 to 10 carbon atoms, or a branched alkoxy group having 3 to 10 carbon atoms.

4. The liquid crystal composition according to claim 1, wherein the mass ratio of the anthraquinone compound represented by the general formula (1) to the anthraquinone compound represented by the general formula (2) is 2:1 to 1:

2.

5. The liquid crystal composition according to claim 1, wherein the content of the dye compound (A) in the liquid crystal composition is 0.5 to 10 parts by mass per 100 parts by mass of the liquid crystal material (B).

6. The liquid crystal composition according to claim 1, comprising the anthraquinone compound represented by the general formula (1) and a dichroic dye other than the anthraquinone compound represented by the general formula (2).

7. A light-adjusting element comprising a pair of opposing substrates, at least one of which is a transparent substrate having a transparent electrode, and the liquid crystal composition according to claim 1 sandwiched between the substrates.

8. The light control element according to claim 7, wherein both of the pair of substrates are transparent substrates having transparent electrodes.

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