Composition, reflective film, laminate, and compound

Abstract

A first problem addressed by the present invention is to provide a composition having excellent HTP. A second problem addressed by the present invention is to provide a reflective film, a laminate, and a compound related to the composition.　A composition according to the present invention comprises a disk-shaped liquid crystal compound and at least one compound selected from the group consisting of compounds represented by formula (1S) and compounds represented by formula (1R).

Description

Compositions, reflective films, laminates, compounds

[0001] The present invention relates to compositions, reflective films, laminates, and compounds.

[0002] Compounds exhibiting liquid crystalline properties (hereinafter also referred to as "liquid crystal compounds") can be applied to a variety of uses. For example, liquid crystal compounds are used in the production of optical anisotropies, such as phase difference films, and in the production of reflective films with a fixed cholesteric liquid crystal phase. Generally, the cholesteric liquid crystal phase is formed by adding a chiral compound to a nematic liquid crystal. An example of a chiral agent is a binaphthyl derivative, which is known to be a chiral compound with a relatively large helical twisting power (HTP).

[0003] For example, Patent Document 1 discloses a composition containing the following chiral compound and liquid crystal compound.

[0004]

[0005] International Publication No. 2021 / 033640

[0006] The present inventors investigated the composition described in Patent Document 1 and found that there is room to further increase the strength of HTP.

[0007] Therefore, the object of the present invention is to provide a composition that is excellent in terms of HTP. Another object of the present invention is to provide a reflective film, a laminate, and a compound related to the above composition.

[0008] As a result of diligent research to solve the above problems, the inventors have found that the above problems can be solved by the following configuration.

[0009] [1] A composition comprising a disc-shaped liquid crystal compound and at least one compound selected from the group consisting of a compound represented by formula (1S) and a compound represented by formula (1R) described later. [2] The composition according to [1], wherein the group represented by formula (Z-1) represents >C=O, >C=S, or a group represented by formula (Za) described later. [3] The composition according to [2], wherein the group represented by formula (Za) represents a group represented by formula (Za1-A) described later. [4] The composition according to any one of [1] to [3], wherein the group represented by formula (X-1) represents a group selected from the group consisting of a group represented by formula (PX1) and a group represented by formula (PX2) described later, or the group represented by formula (Y-1) represents a group selected from the group consisting of a group represented by formula (PY1) and a group represented by formula (PY2) described later. [5] The molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution of the compound represented by formula (1S) and the compound represented by formula (1R) is 1000 L·mol －１ ・cm －１ The composition according to any one of [1] to [4] below. [6] The composition according to any one of [1] to [5] wherein the disc-shaped liquid crystal compound comprises a compound represented by formula (5) described later. [7] The composition according to any one of [1] to [6] further comprises a photopolymerization initiator and a solvent. [8] The composition according to any one of [1] to [7] further comprises a vertical alignment agent. [9] A reflective film formed using the composition according to any one of [1] to [8].

[10] A laminate comprising the reflective film according to [9] and a reflective film formed using a rod-shaped liquid crystal compound.

[11] A compound represented by formula (1S) described later, wherein the molar extinction coefficient of the above compound at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol －１ ・cm －１ The following compounds:

[12] A compound represented by formula (1R) described later, wherein the molar extinction coefficient of the above compound at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol －１ ・cm －１ The following are the compounds.

[0010] According to the present invention, a composition excellent in HTP can be provided. Further, according to the present invention, a reflective film, a laminate, and a compound related to the above composition can also be provided.

[0011] Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments.

[0012] In this specification, a numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value.

[0013] In this specification, each component may be used alone as one kind of substance corresponding to each component, or two or more kinds may be used in combination. Here, when two or more kinds of substances are used in combination for each component, the content of that component refers to the total content of the substances used in combination, unless otherwise specified.

[0014] In this specification, "(meth)acryloyl" is used to mean "either one or both of acryloyl and methacryloyl".

[0015] In this specification, the solid content is intended to be a component forming the composition layer and does not include a solvent. Note that a component forming the composition layer is regarded as a solid content even if its property is liquid as long as it is a component forming the composition layer.

[0016] In this specification, the bonding direction of the divalent group is not limited unless otherwise specified. For example, in a compound represented by the formula "X - Y - Z", when Y is -COO-, Y may be -CO - O - or -O - CO -. Further, the above compound may be "X - CO - O - Z" or "X - O - CO - Z".

[0017] In this specification, unless otherwise specified, monovalent substituents are preferred as substituents. Examples of substituents include monovalent non-metal atomic groups excluding hydrogen atoms. In this specification, when referring to an aromatic ring group, for example, a group formed by removing one or more hydrogen atoms from an aromatic ring can be mentioned. For example, an n-valent aromatic ring group includes a group formed by removing n hydrogen atoms from an aromatic ring. In this specification, when referring to an aromatic hydrocarbon group, a group formed by removing one or more hydrogen atoms from the above aromatic hydrocarbon ring can be mentioned, and when referring to an aromatic heterocyclic group (aromatic hetero ring group), a group formed by removing one or more hydrogen atoms from the above aromatic heterocyclic ring can be mentioned. In this specification, when referring to an alicyclic group, for example, a group formed by removing one or more hydrogen atoms from an alicyclic ring can be mentioned. For example, an n-valent alicyclic group includes a group formed by removing n hydrogen atoms from an alicyclic ring. In this specification, when referring to an aliphatic hydrocarbon ring group, a group formed by removing one or more hydrogen atoms from the above aliphatic hydrocarbon ring can be mentioned, and when referring to an aliphatic heterocyclic group (aliphatic hetero ring group), a group formed by removing one or more hydrogen atoms from the above aliphatic heterocyclic ring can be mentioned.

[0018] In this specification, when referring to the "polymerizable group P", groups represented by the following formulas (P-1) to (P-21) can be mentioned. In formulas (P-1) to (P-21), * represents the bonding position. Also, Ra represents a hydrogen atom or a methyl group. Also, Me represents a methyl group and Et represents an ethyl group.

[0019]

[0020] [Composition] The composition of the present invention includes a discotic liquid crystal compound and at least one compound selected from the group consisting of the compound represented by the following formula (1S) and the compound represented by the following formula (1R) (hereinafter also referred to as "specific compound").

[0021] In aligning liquid crystal compounds to a cholesteric liquid crystal orientation state, it is typically necessary to use an optically active compound (also called a "chiral compound" or "chiral agent"). The present inventors have now revealed that when a specific compound is applied as a chiral agent, particularly when aligning a disc-shaped liquid crystal compound to a cholesteric liquid crystal orientation state, the HTP of the composition increases significantly. While the reason why a composition having the above configuration can solve the problems of the present invention is not entirely clear, the inventors speculate as follows. Note that the following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than those described below, it is still within the scope of the present invention.

[0022] The specific compound has as its main characteristic the hydroxyl group of binaphthol, which is an axially chiral compound, is linked to a predetermined π-conjugated linking group (Z in formula (1S)). １ " and "Z in formula (1R) ２ The characteristics of the specific compound include having a crosslinked structure (corresponding to ") and the fact that the number of π electrons contained in a predetermined position satisfies formula (W-1). The specific compound is presumed to have a structure with excellent π-planarity due to the above characteristics and to have excellent interaction with disc-shaped compounds that typically have a highly planar structure. As a result, it is presumed that when the specific compound is used as a chiral agent when orienting a disc-shaped liquid crystal compound to a cholesteric liquid crystal orientation state, the HTP of the composition will increase significantly. Hereinafter, the superior HTP of the composition of the present invention will also be referred to as "the effects of the present invention are superior."

[0023] The following describes each component of the composition.

[0024] [Disc-shaped liquid crystal compound] The composition of the present invention includes a disc-shaped liquid crystal compound. The term "liquid crystal" means that the compound exhibits the property of creating an intermediate phase between the crystalline phase (low temperature side) and the isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed by observing the compound under a polarizing microscope while heating or cooling it using a Mettler Toledo FP90 hot stage system or the like. Typically, the disc-shaped liquid crystal compound preferably exhibits a discotic nematic liquid crystal phase.

[0025] The discotic liquid crystal compound may be either a low-molecular-weight discotic liquid crystal compound or a high-molecular-weight discotic liquid crystal compound, but in terms of the effects of the present invention being more excellent, it is preferably a low-molecular-weight discotic liquid crystal compound. The discotic liquid crystal compound may have a polymerizable group. The type of the polymerizable group is not particularly limited, but a functional group capable of addition polymerization reaction is preferable, a polymerizable ethylenically unsaturated group or a cyclo-polymerizable group is more preferable, and a (meth)acryloyl group, a vinyl group, a styryl group, or an allyl group is even more preferable.

[0026] Known compounds can be used as the discotic liquid crystal compound. Examples of the discotic liquid crystal compound include the compounds described in paragraphs 0020 to 0067 of JP-A-2007-108732 and paragraphs 0013 to 0108 of JP-A-2010-244038.

[0027] As the discotic liquid crystal compound, a compound represented by the following formula (V) is preferable.

[0028]

[0029] In formula (V), A ２ , A ３ , and A ４ each independently represents —CH═ or —N═. R １７ , R １８ , and R １９ each independently represents a group represented by the following formula (V1-1) or a hydrogen atom. However, at least two of R １７ , R １８ , and R １９ represent a group represented by formula (V1-1). * represents the bonding position to the central ring.

[0030] Formula (V1-1) *-X ２１１ -(Z ２１ -X ２１２ ) ｎ２１ -L ２１ -Y ２１ represents.

[0031] In formula (V1-1), X ２１１ and X <了 ２１２Each of these independently represents a single bond, -O-, -CO-, -O-CO-, -O-CO-O-, -O-CO-NH-, -O-CO-S-, -CO-NH-, -CO-S-, -NH-CO-NH-, -NH-CO-S-, -S-, or -S-CO-S-. ２１１ and X ２１２ Each of these is preferably a single bond or a -O-CO- bond.

[0032] In formula (V1-1), Z ２１ This represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents.

[0033] Z ２１ The aromatic ring in the above-mentioned aromatic ring group represented by may be either a monocyclic structure or a fused-ring structure (i.e., it may be either a monocyclic aromatic ring group or a fused-ring aromatic ring group). When the above-mentioned aromatic ring group is a fused-ring aromatic ring group, it is preferable that it is a fused-ring aromatic ring group formed by the fusion of two to three monocyclic rings. ２１ A preferred embodiment of the above-mentioned aromatic ring group is a divalent aromatic ring group having five or six members, or a fused aromatic ring group formed by the fusion of two or three monorings (for example, a monoring aromatic ring).

[0034] The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. Examples of the above aromatic hydrocarbon group include a benzene ring group and a naphthalene ring group. The above aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of the above aromatic heterocyclic group include the following groups.

[0035]

[0036] In the formula, * represents X ２１１ This represents the site of connection, and ** indicates X ２１２ This represents the site of connection. A ４１ and A ４２ Each of them independently, -CH ２ = or represents a nitrogen atom. X ４ It consists of an oxygen atom, a sulfur atom, and -CH ２ -, or -NR Ｔ Represents -. RＴ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Specific examples of aromatic heterocyclic groups include formulas (X11-1) to (X11-14), which will be described later.

[0037] Z ２１ The alicyclic group represented above may be either a monocyclic or a fused ring. ２１ A preferred embodiment of the above-mentioned alicyclic group is a divalent alicyclic group having a five-membered or six-membered ring.

[0038] Z ２１ The alicyclic group represented above may be either an aliphatic hydrocarbon ring group or an aliphatic heterocyclic group. An example of the aliphatic hydrocarbon ring group is a cyclohexane group. The aliphatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of the aliphatic heterocyclic group include a pyrrolidine ring group, a piperidine ring group, a piperazine ring group, and a morpholine ring group.

[0039] Z ２１ The aromatic ring group and the alicyclic group represented by the above may have substituents. ２１ Examples of substituents that the above aromatic ring group and alicyclic group represented by the above formula may have include halogen atoms, alkyl groups (e.g., 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms), alkoxy groups (e.g., 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms), alkoxycarbonyl groups (e.g., 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms), and acyloxy groups (e.g., 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms).

[0040] In formula (V1-1), L ２１ represents a linear or branched alkylene group, or a linear or branched alkenylene group, and the -CH group present in the alkylene group or the alkenylene group. ２ At least one of the following is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２It may be substituted with -, and at least one of the hydrogen atoms present in the alkylene group and the alkenylene group may be substituted with a substituent (for example, a halogen atom). Ｔ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. However, the -CH present in the alkylene group and the alkenylene group is also included. ２ Two or more hyphens are -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ When replaced with -, adjacent -CH ２ The hyphen is never substituted by the above group.

[0041] L ２１ In particular, linear or branched alkylene groups, or linear or branched alkenylene groups, wherein the alkylene group or the alkenylene group contains -CH ２ At least one of the following is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ It is preferable that the group may be substituted with a negative atom, and that at least one of the hydrogen atoms present in the alkylene group and the alkenylene group may represent a group that is substituted with a halogen atom.

[0042] L ２１ The number of carbon atoms in the alkylene group and alkenylene group represented by the above is preferably 1 to 12, more preferably 1 to 10, and even more preferably 1 to 8. ２１ The alkylene group and alkenylene group represented above, at least one -CH ２ - is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２When having a structure substituted with -, the number of carbon atoms of the alkylene group and the alkenylene group is intended to be the number of carbon atoms counted by the method shown below. L ２１ In the above alkylene group and the above alkenylene group represented by ２１ , -CH ２ - is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ -, or -NR Ｔ -SO ２ - When having a structure substituted with -, the number of carbon atoms is intended to be counted by regarding -CO-, -O-, -S-, or -NR Ｔ - as -CH ２ -. That is, L ２１ For example, when it is a group represented by -CO-O-C ２ H ４ -, the number of carbon atoms of this group is 4. Also, L ２１ For example, when it is a group represented by -CO-N(CH ３ )-C ２ H ４ -, the number of carbon atoms of this group is 4. L ２１ is preferably a linear or branched alkylene group having 1 to 10 carbon atoms, in which at least one -CH ２ - may be substituted with -O- or -CO-.

[0043] In formula (V1-1), Y ２１ represents a hydrogen atom or a monovalent substituent. The monovalent substituent represented by Y ２１ is not particularly limited, and examples include a polymerizable group, a hydroxyl group, a carboxy group, and a halogen atom. As the above polymerizable group, known polymerizable groups are included. From the viewpoint of reactivity, a functional group capable of an addition polymerization reaction is preferable, a polymerizable ethylenically unsaturated group or a ring polymerizable group is more preferable, and a group exemplified as the above polymerizable group P is even more preferable. The monovalent substituent represented by Y ２１ is preferably a polymerizable group.

[0044] In formula (V1-1), n21 represents an integer of 1 to 5. n21 is preferably an integer of 1 to 3, and 2 or 3 is more preferable. When n21 represents an integer of 2 or more, a plurality of Zs present２１ Each other and X ２１２ Each other may be the same or different from each other. In formula (V1-1), * represents a bonding position.

[0045] Among others, the group represented by the above formula (V1-1) is preferably a group represented by the following formula (V1-2). Formula (V1-2) *-X ２１１ -(Z ２１ -X ２１２ ) ｎ２１ -L ２１ -P ２１ represents. *, X in formula (V1-2) ２１１ , Z ２１ , X ２１２ , L ２１ , and n21 are the same as *, X in formula (V1-1) ２１１ , Z ２１ , X ２１２ , L ２１ , and n21, and have the same preferred embodiments. In formula (V1-2), P ２１ represents a polymerizable group. Examples of the above polymerizable group include known polymerizable groups. From the viewpoint of reactivity, a functional group capable of addition polymerization reaction is preferred, a polymerizable ethylenically unsaturated group or a ring polymerizable group is more preferred, and a group exemplified as the above polymerizable group P is even more preferred.

[0046] In formula (V), R １７ , R １８ , and R １９ Among them, it is preferable that two or more represent a group represented by formula (V1-2), and it is more preferable that all of R １７ , R １８ , and R １９ represent a group represented by formula (V1-2).

[0047] For details and specific examples of the compound represented by the general formula (V), for example, refer to the descriptions in paragraphs 0013 to 0077 of JP-A-2010-244038 and paragraphs 0137 to 0141 of JP-A-2007-246672, etc.

[0048] Suitable specific examples of the discotic liquid crystal compound include, for example, the compound represented by formula (5).

[0049]

[0050] In formula (5), T １１ , T １２ , and T １３ Each of them independently, -CH ２ = or represents a nitrogen atom. R １１ , R １２ , and R １３ Each of these independently represents a group or hydrogen atom represented by formula (A1). However, R １１ , R １２ , and R １３ At least two of these represent the base represented by formula (A1). *-X １１ - (Y １１ )n-L １１ - Q １１ (A1) In formula (A1), X １１ This represents a divalent aromatic heterocyclic group represented by formulas (X11-1) to (X11-14), or a divalent fused aromatic ring group formed by the fusion of two to three monorings, which may have substituents.

[0051] Below, X in equation (A1) １１ This represents a divalent aromatic heterocyclic group represented by formulas (X11-1) to (X11-14).

[0052]

[0053] At the point where Δn becomes higher, X １１ It is preferable that represents a divalent aromatic heterocyclic group represented by any of the above formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14), more preferably a divalent aromatic heterocyclic group represented by the above formula (X11-2) or (X11-5), and even more preferably a divalent aromatic heterocyclic group represented by the above formula (X11-2).

[0054] X １１Examples of divalent fused aromatic ring groups represented by the formulas (X51-1) to (X51-20) below include groups obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic ring represented by any of the following formulas. The fused aromatic ring represented by any of the following formulas (X51-1) to (X51-20) may have its hydrogen atoms substituted with substituents as much as possible.

[0055]

[0056] Y １１ represents a divalent aromatic ring group which may have substituents. n represents an integer of 1 or more. Y １１ The aromatic ring group represented above may be either a monocyclic aromatic ring group or a fused aromatic ring group. When the aromatic ring group is a fused aromatic ring group, it is preferable that it is a fused aromatic ring group formed by the fusion of two to three monocyclic rings. １１ A preferred embodiment of the above-mentioned aromatic ring group is a divalent aromatic ring group having five or six members, or a fused aromatic ring group formed by the fusion of two or three monorings (for example, a monoring aromatic ring).

[0057] The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. Examples of the above aromatic hydrocarbon group include a benzene ring group and a naphthalene ring group. The above aromatic heterocyclic group preferably contains at least one heteroatom selected from a nitrogen atom, an oxygen atom, and a sulfur atom as a ring member atom.

[0058] Y １１ Specific examples of divalent aromatic ring groups represented by the formulas (X11-1) to (X11-14) above include, for example, a benzene ring group, a divalent aromatic heterocyclic group represented by the formulas (X11-1) to (X11-14) above, and a group obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic ring represented by any of the formulas (X51-1) to (X51-20) above.

[0059] X １１ A divalent fused aromatic ring group and Y represented by １１ The divalent aromatic ring group represented by may have substituents. １１ A divalent fused aromatic ring group and Y represented by １１Examples of substituents that the divalent aromatic ring group represented by may have include halogen atoms, alkyl groups (e.g., 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms), alkoxy groups (e.g., 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms), alkoxycarbonyl groups (e.g., 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms), and acyloxy groups (e.g., 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms).

[0060] n represents an integer greater than or equal to 1. Preferably, n represents an integer between 1 and 5, and more preferably, an integer between 1 and 3.

[0061] L １１ represents a linear or branched alkylene group or alkenylene group, and -CH present in the alkylene group or alkenylene group. ２ At least one of the following is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ It may be substituted with -, and at least one of the hydrogen atoms present in the alkylene group and the alkenylene group may be substituted with a halogen atom. Ｔ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. However, the -CH present in the alkylene group and the alkenylene group is also included. ２ Two or more hyphens are -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ When replaced with -, adjacent -CH ２ The hyphen is never substituted by the above group.

[0062] L １１ In particular, linear or branched alkylene groups, or linear or branched alkenylene groups, wherein the alkylene group or the alkenylene group contains -CH ２ At least one of the following is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NRＴ - or -NR Ｔ -SO ２ It is preferable that the group may be substituted with a negative atom, and that at least one of the hydrogen atoms present in the alkylene group and the alkenylene group may represent a group that is substituted with a halogen atom.

[0063] L １１ The number of carbon atoms in the alkylene group and alkenylene group represented by the above is preferably 1 to 12, more preferably 1 to 10, and even more preferably 1 to 8. １１ The alkylene group and alkenylene group represented above, at least one -CH ２ - is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ When a structure is substituted with -, the number of carbon atoms in the alkylene group and alkenylene group refers to the number of carbon atoms counted by the method shown below. １１ In the alkylene group and alkenylene group represented above, -CH ２ - is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ If the structure is substituted with -, then -CO-, -O-, -S-, or -NR Ｔ - to - CH ２ - This refers to the number of carbon atoms that can be counted as such. In other words, L １１ However, for example, -CO-O-C ２ H ４ - If it is a group represented by -, the number of carbon atoms in this group is 4. Also, L １１ However, for example, -CO-N(CH ３ )-C ２ H ４ - If it is the group represented, the number of carbon atoms in this group is 4. １１ is at least one -CH ２A linear or branched alkylene group having 1 to 10 carbon atoms is preferred, and the - may be substituted with -O- or -CO-.

[0064] Q １１ This represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. Q １１ It is preferable that this represents a polymerizable group. Examples of polymerizable groups include the polymerizable group P described above.

[0065] In formula (5), R １１ , R １２ , and R １３ It is preferable that all of them represent the group represented by formula (A1). Note that there are multiple X in formula (5). １１ Fellow Y １１ Fellow, L １１ Fellow members, and Q １１ The individuals may be identical or different from one another.

[0066] The following are specific examples of disc-shaped liquid crystal compounds, but are not limited thereto. In the following examples, the three R's at the terminal portions of the disc-shaped liquid crystal compound may be the same or different, but it is preferable that they be the same.

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] In the composition, the content of the disc-shaped liquid crystal compound is preferably 5 to 99% by mass, more preferably 25 to 98% by mass, and even more preferably 75 to 98% by mass, based on the total mass of the solids in the composition. The disc-shaped liquid crystal compound may be used alone or in combination of two or more types. When two or more disc-shaped liquid crystal compounds are used, it is preferable that their total content is within the above numerical range.

[0086] [Specific Compounds] The composition of the present invention comprises at least one compound (specific compound) selected from the group consisting of compounds represented by formula (1S) and compounds represented by formula (1R) described later.

[0087]

[0088] X in equation (1S) １ and X in equation (1R) ２ This represents the base expressed by equation (X-1). Equation (X-1) *-A ｘ１ - (R ｘ１ )n ｘ１ In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ Represents a +1 valent π-conjugated group. R ｘ１ n represents a monovalent substituent. ｘ１ n represents a non-negative integer. ｘ１ If there are two or more, multiple R ｘ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. Aｘ１ If it is a single bond, n ｘ１ This represents 1.

[0089] Y in equation (1S) １ and Y in formula (1R) ２ This represents the base expressed by formula (Y-1). Formula (Y-1) *-A ｙ１ - (R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ Represents a +1 valent π-conjugated group. R ｙ１ n represents a monovalent substituent. ｙ１ n represents a non-negative integer. ｙ１ If there are two or more, multiple R ｙ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. A ｙ１ If it is a single bond, n ｙ１ This represents 1.

[0090] Z in equation (1S) １ and Z in equation (1R) ２ This represents the base expressed by formula (Z-1).

[0091]

[0092] In formula (Z-1), L ｚ１ is, n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１ n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be identical or different from each other. * indicates the joining position.

[0093] However, in formulas (1S) and (1R), the above A ｘ１ , A above ｙ１ , and the above L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1) is satisfied. Equation (W-1) m ｘ１+m ｙ１ +m ｚ１ ≥12

[0094] <Compounds represented by formula (1S)> The compounds represented by formula (1S) will be described below.

[0095] X in equation (1S) １ A represents the group shown in the above formula (X-1). In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ This represents a π-conjugated group with +1 valency. The above π-conjugated group is typically sp ２ These are groups with a conjugated structure composed of atoms that have orbitals. Typically, π-conjugated groups contain π electrons that can contribute to the conjugated system. Examples of π-conjugated groups include aromatic ring groups, those represented as -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S, and sp ２ Examples include atomic groups composed of atoms having orbitals and groups formed by combining them (for example, -CH=CH-CO-, etc.). Note that sp is represented by -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S. ２ The number of π electrons in a divalent π-conjugated group selected from an atomic group composed of atoms with orbitals is always 2. Also, for example, the number of π electrons in a benzene ring group is 6. As will be described later, in formula (X-1), n ｘ１ n represents a non-negative integer. ｘ１ If it is 0 (however, A ｘ１ A (except when it is a hydrogen atom) ｘ１ This represents a monovalent π-conjugated group. An example of a specific form of a monovalent π-conjugated group is the group represented by the following formula (1C). Formula (1C) *-(L ｃ１ ) nc-R ｃ１ L ｃ１ These are sp groups such as divalent aromatic ring groups, -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S. ２ R represents a divalent group selected from an atomic group composed of atoms with orbitals. ｃ１ This is a monovalent aromatic ring group, -CH=CH ２ , -CH=NH, -N=CH ２, and sp such as -N=NH ２ This represents a monovalent group selected from an atomic group composed of atoms having orbitals. nc represents an integer of 0 or more. nc is preferably 0 to 8, more preferably 0 to 6, even more preferably 0 to 3, and particularly preferably 1 or 2. * represents the bond position. When nc represents an integer of 2 or more, multiple L ｃ１ The individuals may be identical or different from one another.

[0096] n in equation (X-1) ｘ１ If A is an integer greater than or equal to 1, ｘ１ n represented by ｘ１ A specific example of a +1 valent π-conjugated group is, for example, the group represented by the above formula (1C) from n ｘ１ This refers to a group formed by removing a certain number of hydrogen atoms.

[0097] L in equation (1C) ｃ１ The divalent aromatic ring group represented by may be either a monocyclic aromatic ring group or a fused aromatic ring group, but it is preferable that it be a monocyclic aromatic ring group. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0098] In formula (X-1), R ｘ１ represents a monovalent substituent. There are no particular restrictions on the monovalent substituent, but sp ２ Atoms that do not have orbitals are A in equation (X-1). ｘ１ It is preferable that the substituent is a monovalent substituent (hereinafter also referred to as a "non-π-conjugated group") at the bonding position with R. ｘ１ The monovalent substituent represented by A ｘ１sp ２ It may have atoms that have orbitals. R ｘ１ The monovalent substituent represented by may have a substituent, and the end (A ｘ１ It may have -O- or -S- at the bonding position with (and may have -O-, -S-, -CO-, and -NR between adjacent carbon atoms (in other words, between carbon atoms) ｑ - A linking group (R) formed by combining one or more selected from the group consisting of - ｑ -O-, -S-, -CO-, and -NR are examples of alkyl groups that may have a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. The alkyl group may be linear, branched, or cyclic, but linear or branched is preferred. The number of atoms other than hydrogen atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 6. Note that between adjacent carbon atoms of the alkyl group there may be -O-, -S-, -CO-, and -NR ｑ - When a linking group is formed by combining one or more selected from the group consisting of -O-, -S-, -CO-, and -NR ｑ Each of the hyphens is counted as having 1 atom. Furthermore, the substituents are not particularly limited, but examples include monovalent aromatic ring groups and the polymerizable group P mentioned above.

[0099] The above R ｘ１ Specific examples of monovalent substituents represented by include alkyl groups, alkoxy groups, alkylthio groups, and alkylcarbonyloxy groups. ｘ１ The alkyl group represented by and the alkyl group portion of the alkylcarbonyloxy group may be linear, branched, or cyclic. Furthermore, the number of carbon atoms is preferably 1 to 6, and more preferably 1 to 4. The above R ｘ１The alkyl portion of the alkoxy group and alkylthio group represented by can be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group and alkylthio group is preferably 1 to 6, and more preferably 1 to 4. The alkyl group, alkoxy group, alkylthio group, and alkylcarbonyloxy group described above may further have substituents. Substituents are not particularly limited, but examples include monovalent aromatic ring groups and the polymerizable group P described above. Note that in formula (X-1), R ｘ１ If there are multiple cases (n ｘ１ If there are two or more R ｘ１ The individuals may be identical or different from one another.

[0100] In formula (X-1), n ｘ１ n represents a non-negative integer. ｘ１ As an upper limit, for example, 10 or less is preferable, and 8 or less is more preferable. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. Also, A ｘ１ If it is a single bond, n ｘ１ This represents 1. In other words, A ｘ１ This represents a hydrogen atom, and n ｘ１ If X represents 0, then X in equation (1S) １ represents a hydrogen atom. Also, A ｘ１ This represents a single bond, and n ｘ１ If X represents 1, then X in equation (1S) １ R ｘ１ This represents a monovalent substituent represented by A. ｘ１ gan ｘ１ When representing a π-conjugated group with +1 valency, n ｘ１ This represents a non-negative integer.

[0101] In equation (X-1), * indicates the bonding position.

[0102] Preferably, the group represented by formula (X-1) represents a group selected from the group consisting of the group represented by formula (PX1) and the group represented by formula (PX2).

[0103] Formula (PX1) *-CR ｘ２ =CR ｘ２ -T ｘａ-T ｘｂ -T ｘｃ In formula (PX1), R ｘ２ Each of these independently represents a hydrogen atom or a monovalent substituent. ｘａ T represents a single bond, >C=O, or >C=S. ｘｂ is a single bond, n ｘ１１ +1 valent aromatic ring group, or n ｘ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｘｃ is, T ｘｂ When this represents a single bond, *-R ｘ３ It represents a group represented by T ｘｂ gan ｘ１１ +1 valent aromatic ring group, or n ｘ１１ When representing a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, the expression *-(R ｘ１ )n ｘ１１ Represents the group represented by R. ｘ１ R represents a monovalent substituent. ｘ３ Each of these independently represents a hydrogen atom or a monovalent substituent. ｘ１１ represents a non-negative integer. * represents the join position.

[0104] In formula (PX1), R ｘ２ Each of these independently represents a hydrogen atom or a monovalent substituent. ｘ２ The monovalent substituent represented by is R in formula (X-1) above. ｘ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. ｘ２ Of these, hydrogen atoms are preferred.

[0105] In formula (PX1), T ｘａ This represents a single bond, >C=O, or >C=S. A single bond is preferred because it has a low molar extinction coefficient at a wavelength of 400 nm and can suppress discoloration.

[0106] In formula (PX1), T ｘｂ is a single bond, n ｘ１１ +1 valent aromatic ring group, or n ｘ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency (hereinafter also referred to as a "ring aggregate group"). It has a low molar extinction coefficient at a wavelength of 400 nm, and can suppress discoloration, which is why it is n ｘ１１A +1 valent aromatic ring group is preferred, n ｘ１１ A monocyclic aromatic ring group with a +1 valent is more preferable.

[0107] The above aromatic ring group may be either a monocyclic aromatic ring group or a fused aromatic ring group, with the monocyclic aromatic ring group being preferred. The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the above aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The above aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0108] The above-mentioned ring aggregate group is a group formed by the linkage of two or more monocyclic aromatic ring groups by single bonds. The number of monocyclic aromatic rings constituting the ring aggregate group is not particularly limited, but 2 to 3 is preferred, and 2 is more preferred. The monocyclic aromatic ring group may be either a monocyclic aromatic hydrocarbon group or a monocyclic aromatic heterocyclic group. An example of a monocyclic aromatic hydrocarbon group is a benzene ring group. A monocyclic aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of monocyclic aromatic heterocyclic groups include groups containing monocyclic aromatic heterocycles with 4 to 6 ring member atoms, such as thiophene, furan, pyridine, pyrrole, triazine, imidazole, triazole, thiadiazole, and thiazole.

[0109] In formula (PX1), T ｘｃ is, T ｘｂ When this represents a single bond, *-R ｘ３ It represents a group represented by T ｘｂ gan ｘ１１ +1 valent aromatic ring group, or n ｘ１１ When representing a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, the expression *-(R ｘ１)n ｘ１１ This represents the base represented by *-R ｘ３ In the group represented by *, * indicates the bond position, R ｘ３ R represents a hydrogen atom or a monovalent substituent. ｘ３ The monovalent substituent represented by is R in formula (X-1) above. ｘ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. *-(R ｘ１ )n ｘ１１ In the group represented by *, * indicates the bond position, R ｘ１ represents a monovalent substituent, n ｘ１１ This represents a non-negative integer. *-(R ｘ１ )n ｘ１１ R in the base represented by ｘ１ The monovalent substituent represented by is R in formula (X-1) above. ｘ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. *-(R ｘ１ )n ｘ１１ In a base represented by n Ｘ１１ n represents a non-negative integer. Ｘ１１ As an upper limit, for example, 10 or less is preferred, 8 or less is more preferred, 6 or less is even more preferred, 4 or less is even more preferred, 3 or less is particularly preferred, and 2 or less is most preferred. Ｘ１１ In one embodiment, it is preferable to represent an integer from 0 to 4, more preferably to represent an integer from 0 to 3, and even more preferably to represent an integer from 0 to 2.

[0110] In formula (PX1), * indicates a bonding position.

[0111] Formula (PX2) *-Ar ｘａ - (R ｘ１ )n ｘ１１ In formula (PX2), Ar ｘａ is, n ｘ１１ +1 valent aromatic ring group, or n ｘ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｘ１ n represents a monovalent substituent. ｘ１ represents an integer greater than or equal to 0. In expression (PX2), Ar ｘａ n represented by ｘ１１ The +1 valent aromatic ring group is T in formula (PX1).ｘｂ n represented by ｘ１１ This is synonymous with a +1 valent aromatic ring group, and the preferred embodiment is the same. Ar ｘａ n ｘ１１ A group consisting of two or more monocyclic aromatic ring groups linked by a single bond, which is +1 valent, is represented by the T in formula (PX1). ｘｂ n ｘ１１ This is synonymous with a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, and the preferred embodiment is the same. In formula (PX2), R ｘ１ , n ｘ１１ , and * are R in formula (PX1), respectively. ｘ１ , n ｘ１１ , and * are synonymous, and the preferred embodiment is the same.

[0112] In equation (1S), X １ The following are specific examples, but are not limited to these. Note that in the following examples, R ｘ１ This is R in the above equation (X-1). ｘ１ This is synonymous with the same as the preferred embodiment. ｘ２ , R ｘ３ , and n ｘ１１ This is R in the above formula (PX1). ｘ２ , R ｘ３ , and n ｘ１１ This is synonymous with the same thing, and the preferred embodiment is also the same. ｘ１１ In particular, it is preferable that it represents an integer between 0 and 4, more preferably that it represents an integer between 0 and 3, and even more preferably that it represents an integer between 0 and 2.

[0113]

[0114] Y in equation (1S) １ A represents the group shown in the above formula (Y-1). In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ This represents a +1 valent π conjugated group. As will be explained later, n in formula (Y-1) ｙ１ n represents a non-negative integer. ｙ１ If it is 0 (however, A ｙ１ A (except when it is a hydrogen atom) ｙ１This represents a monovalent π-conjugated group. An example of a specific form of a monovalent π-conjugated group is the group represented by the following formula (1D). Formula (1D) *-(L ｄ１ )nd-R ｄ１ L ｄ１ These are sp groups such as divalent aromatic ring groups, -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S. ２ R represents a divalent group selected from an atomic group composed of atoms with orbitals. ｄ１ This is a monovalent aromatic ring group, -CH=CH ２ , -CH=NH, -N=CH ２ , and sp such as -N=NH ２ This represents a monovalent group selected from an atomic group composed of atoms having orbitals. nd represents an integer of 0 or more. nd is preferably 0 to 8, more preferably 0 to 6, even more preferably 0 to 3, and particularly preferably 1 or 2. * represents the bond position. When nd represents an integer of 2 or more, multiple L ｄ１ The individuals may be identical or different from one another.

[0115] n in equation (Y-1) ｙ１ If A is an integer greater than or equal to 1, ｙ１ n represented by ｙ１ A specific example of a +1 valent π-conjugated group is, for example, the group represented by the above formula (1D) n ｙ１ This refers to a group formed by removing a certain number of hydrogen atoms.

[0116] In the above formula (1D), L ｄ１The divalent aromatic ring group represented by may be either a monocyclic aromatic ring group or a fused aromatic ring group, but it is preferable that it be a monocyclic aromatic ring group. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0117] In formula (Y-1), R ｙ１ represents a monovalent substituent. There are no particular restrictions on the monovalent substituent, but sp ２ Atoms that do not have orbitals are A in equation (Y-1). ｙ１ It is preferable that the substituent is a monovalent substituent (hereinafter also referred to as a "non-π-conjugated group") at the bonding position with R. ｙ１ The monovalent substituent represented by A ｙ１ sp ２ It may have atoms that have orbitals. R ｙ１ The monovalent substituent represented by may have a substituent, and the end (A ｙ１ It may have -O- or -S- at the bonding position with (and may have -O-, -S-, -CO-, and -NR between adjacent carbon atoms (in other words, between carbon atoms) ｑ - A linking group (R) formed by combining one or more selected from the group consisting of - ｑ-O-, -S-, -CO-, and -NR are examples of alkyl groups that may have a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. The alkyl group may be linear, branched, or cyclic, but linear or branched is preferred. The number of atoms other than hydrogen atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 6. Note that between adjacent carbon atoms of the alkyl group there may be -O-, -S-, -CO-, and -NR ｑ - When a linking group is formed by combining one or more selected from the group consisting of -O-, -S-, -CO-, and -NR ｑ Each of the hyphens is counted as having 1 atom. Furthermore, the substituents are not particularly limited, but examples include monovalent aromatic ring groups and the polymerizable group P mentioned above.

[0118] The above R ｙ１ Specific examples of monovalent substituents represented by include alkyl groups, alkoxy groups, alkylthio groups, and alkylcarbonyloxy groups. ｙ１ The alkyl group represented by and the alkyl group portion of the alkylcarbonyloxy group may be linear, branched, or cyclic. Furthermore, the number of carbon atoms is preferably 1 to 6, and more preferably 1 to 4. The above R ｙ１ The alkyl portion of the alkoxy group and alkylthio group represented by can be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group and alkylthio group is preferably 1 to 6, and more preferably 1 to 4. The alkyl group, alkoxy group, alkylthio group, and alkylcarbonyloxy group described above may further have substituents. Substituents are not particularly limited, but examples include monovalent aromatic ring groups and the polymerizable group P described above. Note that in formula (Y-1), R ｙ１ If there are multiple cases (n ｙ１ If there are two or more R ｙ１ The individuals may be identical or different from one another.

[0119] In formula (Y-1), n ｙ１ n represents a non-negative integer. ｙ１As an upper limit, for example, 10 or less is preferable, and 8 or less is more preferable. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. Also, A ｙ１ If it is a single bond, n ｙ１ This represents 1. In other words, A ｙ１ This represents a hydrogen atom, and n ｙ１ If represents 0, then Y in equation (1S) １ represents a hydrogen atom. Also, A ｙ１ This represents a single bond, and n ｙ１ If represents 1, then Y in equation (1S) １ R ｙ１ This represents a monovalent substituent represented by A. ｙ１ gan ｙ１ When representing a π-conjugated group with +1 valency, n ｙ１ This represents a non-negative integer.

[0120] In equation (Y-1), * indicates the bonding position.

[0121] Preferably, the group represented by formula (Y-1) represents a group selected from the group consisting of the group represented by formula (PY1) and the group represented by formula (PY2).

[0122] Formula (PY1) *-CR ｙ２ =CR ｙ２ -T ｙａ -T ｙｂ -T ｙｃ In formula (PY1), R ｙ２ Each of these independently represents a hydrogen atom or a monovalent substituent. ｙａ T represents a single bond, >C=O, or >C=S. ｙｂ is a single bond, n ｙ１１ +1 valent aromatic ring group, or n ｙ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｙｃ is, T ｙｂ When this represents a single bond, *-R ｙ３ It represents a group represented by T ｙｂ gan ｙ１１ +1 valent aromatic ring group, or n ｙ１１ When representing a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, the expression *-(R ｙ１ )nｙ１１ Represents the group represented by R. ｙ１ R represents a monovalent substituent. ｙ３ Each of these independently represents a hydrogen atom or a monovalent substituent. ｙ１１ represents a non-negative integer. * represents the join position.

[0123] In formula (PY1), R ｙ２ Each of these independently represents a hydrogen atom or a monovalent substituent. ｙ２ The monovalent substituent represented by is R in formula (Y-1) above. ｙ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. ｙ２ Of these, hydrogen atoms are preferred.

[0124] In formula (PY1), T ｙａ This represents a single bond, >C=O, or >C=S. A single bond is preferred because it has a low molar extinction coefficient at a wavelength of 400 nm and can suppress discoloration.

[0125] In formula (PY1), T ｙｂ is a single bond, n ｙ１１ +1 valent aromatic ring group, or n ｙ１１ This represents a group (ring aggregate group) consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. It has a low molar extinction coefficient at a wavelength of 400 nm, which suppresses discoloration, and is therefore n ｙ１１ A +1 valent aromatic ring group is preferred, n ｙ１１ A monocyclic aromatic ring group with a +1 valent is more preferable.

[0126] The above aromatic ring group may be either a monocyclic aromatic ring group or a fused aromatic ring group, with the monocyclic aromatic ring group being preferred. The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the above aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The above aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0127] The above-mentioned ring aggregate group is a group formed by the linkage of two or more monocyclic aromatic ring groups by single bonds. The number of monocyclic aromatic rings constituting the ring aggregate group is not particularly limited, but 2 to 3 is preferred, and 2 is more preferred. The monocyclic aromatic ring group may be either a monocyclic aromatic hydrocarbon group or a monocyclic aromatic heterocyclic group. An example of a monocyclic aromatic hydrocarbon group is a benzene ring group. A monocyclic aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of monocyclic aromatic heterocyclic groups include groups containing monocyclic aromatic heterocycles with 4 to 6 ring member atoms, such as thiophene, furan, pyridine, pyrrole, triazine, imidazole, triazole, thiadiazole, and thiazole.

[0128] In formula (PY1), T ｙｃ is, T ｙｂ When this represents a single bond, *-R ｙ３ It represents a group represented by T ｙｂ gan ｙ１１ +1 valent aromatic ring group, or n ｙ１１ When representing a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, the expression *-(R ｙ１ )n ｙ１１ This represents the base represented by *-R ｙ３ In the group represented by *, * indicates the bond position, Rｙ３ R represents a hydrogen atom or a monovalent substituent. ｙ３ The monovalent substituent represented by is R in formula (Y-1) above. ｙ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. *-(R ｙ１ )n ｙ１１ In the group represented by *, * indicates the bond position, R ｙ１ represents a monovalent substituent, n ｙ１１ This represents a non-negative integer. *-(R ｙ１ )n ｙ１１ R in the base represented by ｙ１ The monovalent substituent represented by is R in formula (Y-1) above. ｙ１ This is synonymous with the substituent represented by , and the preferred embodiment is the same. *-(R ｙ１ )n ｙ１１ In a base represented by n ｙ１１ n represents a non-negative integer. ｙ１１ As an upper limit, for example, 10 or less is preferred, 8 or less is more preferred, 6 or less is even more preferred, 4 or less is even more preferred, 3 or less is particularly preferred, and 2 or less is most preferred. ｙ１１ In one embodiment, it is preferable to represent an integer from 0 to 4, more preferably to represent an integer from 0 to 3, and even more preferably to represent an integer from 0 to 2.

[0129] In formula (PY1), * indicates a bond position.

[0130] Formula (PY2) *-Ar ｙａ - (R ｙ１ )n ｙ１１ In formula (PY2), Ar ｙａ is, n ｙ１１ +1 valent aromatic ring group, or n ｙ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｙ１ n represents a monovalent substituent. ｙ１ Ar represents a non-negative integer. In formula (PY2), Ar ｙａ n represented by ｙ１１ The +1 valent aromatic ring group is T in formula (PY1). ｙｂ n represented by ｙ１１ This is synonymous with a +1 valent aromatic ring group, and the preferred embodiment is the same. Ar ｙａn ｙ１１ A group consisting of two or more monocyclic aromatic ring groups linked by a single bond, which is +1 valent, is represented by the T in formula (PY1). ｙｂ n ｙ１１ This is synonymous with a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, and the preferred embodiment is the same. In formula (PY2), R ｙ１ , n ｙ１１ , and * are R in formula (PY1), respectively. ｙ１ , n ｙ１１ , and * are synonymous, and the preferred embodiment is the same.

[0131] In the following equation (1S), Y １ The following are specific examples, but are not limited to these. Note that in the following examples, R ｙ１ This is R in the above equation (Y-1). ｙ１ This is synonymous with the same as the preferred embodiment. ｙ２ , R ｙ３ , and n ｙ１１ This is R in the above equation (PY1). ｙ２ , R ｙ３ , and n ｙ１１ This is synonymous with the same thing, and the preferred embodiment is also the same. ｙ１１ In particular, it is preferable that it represents an integer between 0 and 4, more preferably that it represents an integer between 0 and 3, and even more preferably that it represents an integer between 0 and 2.

[0132]

[0133] Z in equation (1S) １ This represents the group expressed by the above formula (Z-1).

[0134] The following describes the group represented by formula (Z-1). In formula (Z-1), L ｚ１ is, n ｚ１ This represents a +2 valent π conjugated group. As will be explained later, n in formula (Z-1) ｚ１ L represents a non-negative integer. ｚ１ If >C=O or >C=S, then n ｚ１ represents 0.

[0135] In the base represented by formula (Z-1), n ｚ１ If L is 0, ｚ１This represents a divalent π-conjugated group. Specific examples of divalent π-conjugated groups include groups represented by >C=O, >C=S, or the following formula (1E).

[0136]

[0137] In formula (1E), Ar ｚ is, n ｅ１ +2 valent aromatic ring group, or n ｅ１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +2 valency. ｅ１ and L ｅ２ Each of these is independently a single bond, or sp bonds such as >C=O and >C=S. ２ This represents a divalent group selected from an atomic group composed of atoms that have orbitals. ｅ１ and L ｅ２ It is preferable that both represent the same group, and that both represent >C=O. ｅ３ These are single bonds or divalent aromatic ring groups, -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S sp ２ R represents a divalent group selected from an atomic group composed of atoms with orbitals. ｅ１ This is a hydrogen atom, or a monovalent aromatic ring group, -CH=CH ２ , -CH=NH, -N=CH ２ , and sp such as -N=NH ２ This represents a monovalent group selected from an atomic group composed of atoms having orbitals. ne1 represents an integer of 0 or greater. ne1 is preferably 0 to 8, more preferably 0 to 6, even more preferably 0 to 3, and particularly preferably 1 or 2.

[0138] n in equation (Z-1) ｚ１ If L is an integer greater than or equal to 1, ｚ１ n represented by ｚ１ A specific example of a +2 valent π-conjugated group is, for example, the group represented by the above formula (1E) from n ｚ１ This refers to the group formed by removing one hydrogen atom. In formula (1E), * indicates a bond position.

[0139] Ar in the above formula (1E) ｚ , L ｅ３ , and R ｅ１The aromatic ring group in the above may be either a monocyclic aromatic ring group or a fused aromatic ring group, with the monocyclic aromatic ring group being preferred. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0140] In the ring aggregate group (ring aggregate group) formed by two or more monocyclic aromatic ring groups linked by single bonds in formula (1E) above, the number of monocyclic aromatic rings constituting the ring aggregate group is not particularly limited, but 2 to 3 is preferred, and 2 is more preferred. The monocyclic aromatic ring group may be either a monocyclic aromatic hydrocarbon group or a monocyclic aromatic heterocyclic group. An example of a monocyclic aromatic hydrocarbon group is a benzene ring group. A monocyclic aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of monocyclic aromatic heterocyclic groups include groups containing monocyclic aromatic heterocycles with 4 to 6 ring member atoms, such as thiophene, furan, pyridine, pyrrole, triazine, imidazole, triazole, thiadiazole, and thiazole.

[0141] In formula (Z-1), R ｚ１ R represents a monovalent substituent. ｚ１ The monovalent substituent represented by is R in formula (X-1) above. ｘ１ This is synonymous with the monovalent substituent represented by , and the preferred embodiment is the same. ｚ１ If there are two or more, multiple R ｚ１ The same or different elements may be identical to each other.

[0142] In formula (Z-1), n ｚ１n represents a non-negative integer. ｚ１ As an upper limit, for example, 10 or less is preferable, and 8 or less is more preferable. In formula (Z-1), * represents the bond position.

[0143] In formula (1S), the group represented by formula (Z-1) is preferably >C=O, >C=S, or the group represented by formula (Za), and more preferably represents formula (Za1-A).

[0144]

[0145] In equation (Za), Ar ｚａ * represents the group represented by formula (Za1) or the group represented by formula (Za2). * represents the bond position.

[0146]

[0147] In formula (Za1), Ar ｚａ１ is, n ｚａ１ This represents a +2 valent aromatic ring group. The above aromatic ring group may be either a monocyclic aromatic ring group or a fused aromatic ring group, with monocyclic aromatic ring groups being preferred. The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group (aromatic heterocyclic group). Examples of the above aromatic hydrocarbon group include groups containing aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The above aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocyclic groups include groups containing aromatic heterocyclic rings having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0148] In formula (Za1), L ｚａ１ L represents a single bond or a divalent π-conjugated group. ｚａ１ A specific example of a divalent π-conjugated group represented by the formula (2E) below is the group represented by the formula (2E) below. Note that the "-L" in formula (1E) above is used in formula (1E) above. ｅ３ ―R ｅ１"R" in the structural part represented by " ｅ１ This corresponds to the group formed by removing one hydrogen atom from ". Formula (2E) *-L ｅ３ -L ｅ４ - * L ｅ３ These are single bonds or divalent aromatic ring groups, -CH=CH-, -CH=N-, -N=N-, >C=O, and >C=S sp ２ This represents a divalent group selected from an atomic group composed of atoms with orbitals. ｅ４ These include divalent aromatic ring groups, -CH=CH-, -CH=N-, and -N=N-, etc. ２ This represents a divalent group selected from an atomic group composed of atoms that have orbitals.

[0149] In formula (Za1), R ｚａ１ R represents a monovalent substituent. ｚａ１ The monovalent substituent represented by is R in formula (Z-1) above. ｚ１ This is equivalent to the monovalent substituent represented by and the preferred embodiment is the same. Note that in formula (Za1), n ｚａ１ If there are two or more, multiple L ｚａ１ R with each other and with multiple Rs ｚａ１ They may be the same or different from one another.

[0150] In formula (Za1), n ｚａ１ n represents a non-negative integer. ｚａ１ As an upper limit, for example, 10 or less is preferable, and 8 or less is more preferable. In formula (Za1), * represents the bond position.

[0151] The group represented by formula (Za1) is preferably the group represented by formula (Za1-A).

[0152]

[0153] Ar ｚａ１１ n includes at least two carbon atoms (corresponding to the carbon atoms in the -C=C- region explicitly shown in the formula). ｚａ１This represents a valence aromatic ring. The aromatic ring may be either a monocyclic aromatic ring group or a fused aromatic ring group, with a monocyclic aromatic ring group being preferred. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of the aromatic hydrocarbon ring include aromatic hydrocarbon rings having 6 to 18 carbon atoms, such as benzene, naphthalene, anthracene, and naphthacene. The aromatic heterocycle preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of aromatic heterocycles include aromatic heterocycles having 4 to 20 ring member atoms, such as thiophene, furan, pyridine, pyrrole, benzothiophene, benzofuran, benzopyrrole, triazine, imidazole, benzimidazole, triazole, thiadiazole, and thiazole.

[0154] L in equation (Za1-A) ｚａ１ , R ｚａ１ , n ｚａ１ , and * are L in formula (Za1). ｚａ１ , R ｚａ１ , n ｚａ１ , and * are synonymous, and the preferred embodiment is the same. Note that n ｚ１ If there are two or more, multiple R ｚ１ The same or different elements may be identical to each other.

[0155]

[0156] In formula (Za2), Ar ｚａ２ is, n Ｚａ１ This represents a +2 valent monocyclic aromatic ring group. The above monocyclic aromatic ring group may be either a monocyclic aromatic hydrocarbon group or a monocyclic aromatic heterocyclic group. An example of a monocyclic aromatic hydrocarbon group is a benzene ring group. A monocyclic aromatic heterocyclic group preferably contains at least one heteroatom selected from nitrogen, oxygen, and sulfur atoms as a ring member atom. Examples of monocyclic aromatic heterocyclic groups include groups containing monocyclic aromatic heterocycles with 4 to 6 ring member atoms, such as thiophene, furan, pyridine, pyrrole, triazine, imidazole, triazole, thiadiazole, and thiazole.

[0157] n Ｚｂ１Ar represents 2 or 3, and preferably represents 2. ｚａ２ The elements may be identical or different from each other, but it is preferable that they be identical.

[0158] L in equation (Za2) ｚａ１ , R ｚａ１ , n ｚａ１ , and * are L in formula (Za1). ｚａ１ , R ｚａ１ , n ｚａ１ , and * are synonymous, and the preferred embodiment is the same. Note that n ｚａ１ If there are two or more, multiple L ｚａ２ R with each other and with multiple Rs ｚａ２ They may be the same or different from one another.

[0159] In the following equation (1S), Z １ The following are specific examples, but are not limited to these. Note that in the following examples, R ｚ１ and n ｚ１ R in equation (Z-1) ｚ１ and n ｚ１ This is synonymous with the same as the preferred embodiment. ｚ２ R represents a hydrogen atom or a monovalent substituent. ｚ２ As a monovalent substituent represented by formula (Z-1), R ｚ１ Examples of monovalent substituents represented by are the same, and the preferred embodiments are also the same. ｚ１１ The symbol represents an integer between 0 and 4, preferably between 0 and 3, and more preferably between 0 and 2. The asterisk (*) indicates a combination position.

[0160]

[0161]

[0162] Equation (1S) is the same as above A in equation (X-1) above. ｘ１ , in the above formula (Y-1) above A ｙ１ , and the above L in formula (Z-1) ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1) is satisfied. Equation (W-1) m ｘ１+m ｙ１ +m ｚ１ ≥12 The present invention has superior effects, m ｘ１ +m ｙ１ +m ｚ１ The value of m is preferably 18 or higher, more preferably 21 or higher, and even more preferably 22 or higher. ｘ１ +m ｙ１ +m ｚ１ There is no particular upper limit to the value, but it is usually 50 or less, preferably 40 or less, more preferably 30 or less, even more preferably 28 or less, and particularly preferably 26 or less.

[0163] The molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution of the compound represented by formula (1S) is 1000 L·mol －１ ・cm －１ Preferably, it is 500 L·mol －１ ・cm －１ It is more preferable that the following is true: 200 L·mol －１ ・cm －１ It is even more preferable that the following conditions are met. The lower limit is 0 L·mol. －１ ・cm －１ The above is preferable. A lower molar extinction coefficient at a wavelength of 400 nm is more preferable because it suppresses discoloration.

[0164] The following are specific examples of compounds represented by formula (1S).

[0165]

[0166] <Compounds represented by formula (1R)> The compounds represented by formula (1R) will be explained below. X in formula (1R) ２ , Y ２ , and Z ２ X in equation (1S) １ , Y １ , and Z １This is synonymous with the above, and the preferred embodiments are also the same. In other words, the compound represented by formula (1R) has the same structure as the compound represented by formula (1S) described above, except that the binaphthyl structural site, which is the parent core, is the R-isomer, and the preferred embodiments are also the same. Note that the compound represented by formula (1S) described above is a compound in which the binaphthyl structural site, which is the parent core, is the S-isomer. Formula (1R) is the same as the above A in formula (X-1) described above. ｘ１ , in the above formula (Y-1) above A ｙ１ , and the above L in formula (Z-1) ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1) is satisfied. Equation (W-1) m ｘ１ +m ｙ１ +m ｚ１ ≥12 The present invention has superior effects, m ｘ１ +m ｙ１ +m ｚ１ The value of m is preferably 18 or higher, more preferably 21 or higher, and even more preferably 22 or higher. ｘ１ +m ｙ１ +m ｚ１ There is no particular upper limit to the value, but it is usually 50 or less, preferably 40 or less, more preferably 30 or less, even more preferably 28 or less, and particularly preferably 26 or less.

[0167] The molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution of the compound represented by formula (1R) is 1000 L·mol －１ ・cm －１ Preferably, it is 500 L·mol －１ ・cm －１ It is more preferable that the following is true: 200 L·mol －１ ・cm －１ It is even more preferable that the following conditions are met. The lower limit is 0 L·mol. －１ ・cm －１ The above is preferable. A lower molar extinction coefficient at a wavelength of 400 nm is more preferable because it suppresses discoloration.

[0168] Specific examples of compounds represented by formula (1R) include the R-form of the specific compound represented by formula (1S) exemplified in the section above.

[0169] The content of the specific compound in the composition is not particularly limited, but it is preferably 0.1 to 20% by mass, more preferably 1 to 15% by mass, and even more preferably 2 to 10% by mass, relative to the total mass of the liquid crystal compound in the composition. The composition may use one specific compound alone or two or more. When two or more are used, it is preferable that their total content is within the above range.

[0170] [Polymerization Initiator] The composition may contain a polymerization initiator. Examples of polymerization initiators include photopolymerization initiators and thermal polymerization initiators, among which photopolymerization initiators that can initiate the polymerization reaction by ultraviolet irradiation are preferred. Examples of photopolymerization initiators include alkylphenone compounds, α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, phenazine compounds, and oxadiazole compounds. When the composition contains a polymerization initiator, the content of the polymerization initiator in the composition is not particularly limited, but it is preferably 0.1 to 20% by mass, and more preferably 1 to 8% by mass, relative to the total mass of the liquid crystal compound. The composition may use one polymerization initiator alone or two or more. When two or more are used, it is preferable that their total content is within the above range.

[0171] [Vertical Alignment Agent] The composition may also preferably contain a vertical alignment agent. The inclusion of a vertical alignment agent in the composition makes it easier to achieve superior orientation of the disc-shaped liquid crystal compound, and thus enhances the effects of the present invention. As the vertical alignment agent, compounds known as vertical alignment agents for disc-shaped liquid crystal compounds can be used. For example, boronic acid compounds and onium salt compounds (preferably quaternary ammonium salt compounds) can be used, and specifically, compounds described in paragraphs

[0023] to

[0032] of Japanese Patent Application Publication No. 2008-225281, paragraphs

[0052] to

[0058] of Japanese Patent Application Publication No. 2012-208397, paragraphs

[0024] to

[0055] of Japanese Patent Application Publication No. 2008-026730, paragraphs

[0043] to

[0055] of Japanese Patent Application Publication No. 2016-193869, etc., can be referenced, and this information is incorporated herein.

[0172] Specific examples of quaternary ammonium salt compounds include, for example, compounds represented by the following formula (AM).

[0173]

[0174] In formula (AM), ring A represents a quaternary ammonium ion consisting of a nitrogen-containing heterocycle. X represents an anion. １ L represents a divalent linking group. ２ This represents a single bond or a divalent linking group. １ represents a divalent linking group having a 5-membered or 6-membered ring as a substructure. Z represents a divalent linking group having 2 to 20 alkylene groups as a substructure. P １ and P ２ Each of these independently represents a hydrogen atom, a hydroxyl group, a carbonyl group, a carboxyl group, an amino group, a nitro group, an ammonium group, a cyano group, or a polymerizable group (preferably a group exemplified by polymerizable group P).

[0175] Ring A represents a quaternary ammonium ion consisting of a nitrogen-containing heterocycle. Examples of ring A include pyridine rings, picoline rings, 2,2'-bipyridyl rings, 4,4'-bipyridyl rings, 1,10-phenanthroline rings, quinoline rings, oxazole rings, thiazole rings, imidazole rings, pyrazine rings, triazole rings, and tetrazole rings. A quaternary imidazolium ion or a quaternary pyridinium ion is preferred as ring A.

[0176] X represents an anion. Specific examples of X include halogen anions (e.g., fluoride ion, chloride ion, bromide ion, iodide ion, etc.), sulfonate ions (e.g., methanesulfonate ion, trifluoromethanesulfonate ion, methylsulfate ion, vinylsulfonate ion, allylsulfonate ion, p-toluenesulfonate ion, p-chlorobenzenesulfonate ion, p-vinylbenzenesulfonate ion, 1,3-benzenedisulfonate ion, 1,5-naphthalenedisulfonate ion, 2,6-naphthalenedisulfonate ion, etc.), sulfate ions, carbonate ions, nitrate ions, thiocyanate ions, perchlorate ions, tetrafluoroborate ions, picrate ions, acetate ions, benzoate ions, p-vinylbenzoate ions, formate ions, trifluoroacetate ions, phosphate ions (e.g., hexafluorophosphate ions), and hydroxide ions.

[0177] L １ Specific examples of divalent linking groups represented by include alkylene groups, -O-, -S-, -CO-, and -SO ２ Examples include divalent linking groups having 1 to 20 carbon atoms, consisting of one or more combinations of the group comprising -, -NRa- (where Ra is an alkyl group or hydrogen atom having 1 to 5 carbon atoms), alkenylene group, alkynylene group, and arylene group. １ Among these, -AL-, -O-AL-, -CO-O-AL-, or -O-CO-AL- are preferred. AL represents an alkylene group having 1 to 10 carbon atoms.

[0178] L ２Specific examples of the divalent linking group represented by include divalent linking groups having 1 to 10 carbon atoms, consisting of one or more combinations of groups from the group consisting of alkylene groups, -O-, -S-, -CO-, -SO2-, -NRa- (where Ra is an alkyl group or hydrogen atom having 1 to 5 carbon atoms), alkenylene groups, alkynylene groups, and arylene groups. ２ Among these, single bonds, -O-, -O-CO-, -CO-O-, -O-AL-O-, -O-AL-O-CO-, -O-AL-CO-O-, -CO-O-AL-O-, -CO-O-AL-O-CO-, -CO-O-AL-CO-O-, -O-CO-AL-O-CO-, -O-CO-AL-O-CO-, or -O-CO-AL-CO-O-. Note that AL represents an alkylene group having 1 to 10 carbon atoms.

[0179] Y １ Y represents a divalent linking group that may have substituents and has a 5 or 6-membered ring as a substructure. １ Specific examples include cyclohexyl rings, aromatic hydrocarbon rings, and heterocycles. Specific examples of aromatic hydrocarbon rings include benzene rings, indene rings, naphthalene rings, fluorene rings, phenanthrene rings, anthracene rings, biphenyl rings, and pyrene rings. The heterocycles may be either aromatic heterocycles or aliphatic heterocycles. Specific examples of heterocycles include furan rings, thiophene rings, pyrrole rings, pyrroline rings, pyrrolidine rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, imidazoline rings, imidazolidine rings, pyrazole rings, pyrazoline rings, pyrazolidine rings, triazole rings, furazan rings, tetrazole rings, pyran rings, dioxane rings, dithiane rings, thiine rings, pyridine rings, piperidine rings, oxazine rings, morpholine rings, thiazine rings, pyridazine rings, pyrimidine rings, pyrazine rings, piperazine rings, and triazine rings.

[0180] The above Y １Specific examples of substituents on a divalent linking group having a 5 or 6-membered ring as a substructure include halogen atoms, cyano groups, alkyl groups (e.g., 1 to 12 carbon atoms), alkenyl groups (e.g., 2 to 12 carbon atoms), alkoxy groups (e.g., 1 to 12 carbon atoms), and acyl groups (e.g., 2 to 12 carbon atoms). The substituents may be further substituted with other substituents.

[0181] Y １ The divalent linking group represented by is preferably a divalent linking group having two or more 5 or 6-membered rings, and more preferably has a structure in which two or more rings are linked by single bonds or divalent linking groups. As for the divalent linking group, the above L １ and the above L ２ The divalent linking group shown is represented by , and can be selected from the group consisting of -C≡C-, -CH=CH-, -CH=N-, -N=CH-, and -N=N-.

[0182] Z represents a divalent linking group having an alkylene group with 2 to 20 carbon atoms as a substructure, and consisting of a combination of -O-, -S-, -CO-, and -SO2-, where the alkylene group may have substituents. Examples of divalent linking groups include alkylene oxy groups and polyalkylene oxy groups. The number of carbon atoms in the alkylene group represented by Z is preferably 2 to 16, more preferably 2 to 12, and even more preferably 2 to 8.

[0183] P 1 and P 2 Each of these independently represents a monovalent substituent having a polymerizable ethylenically unsaturated group, a hydrogen atom, a hydroxyl group, a carbonyl group, a carboxyl group, a substituted or unsubstituted amino group (e.g., a dialkylamino group), a nitro group, an ammonium group, or a cyano group.

[0184] For compounds represented by formula (AM), for example, reference can be made to paragraphs

[0150] to

[0183] of Japanese Patent Application Publication No. 2013-235232, which are incorporated into the present specification.

[0185] When the composition contains a vertical alignment agent, the content of the vertical alignment agent is not particularly limited, but it is preferably 0.001 to 10% by mass, and more preferably 0.05 to 3% by mass, relative to the total mass of the liquid crystal compound. The composition may use one type of vertical alignment agent alone or two or more types. When two or more types are used, it is preferable that their total content is within the above range.

[0186] [Adhesive] The composition may also preferably contain an adhesive. A boronic acid compound is preferred as the adhesive. A specific example of a boronic acid compound is a compound represented by the following formula (BT).

[0187]

[0188] In formula (BT), R １ and R ２ Each of these independently represents a hydrogen atom, a potentially substituted monovalent aliphatic hydrocarbon group, or a potentially substituted monovalent aromatic ring group. １ and R ２ These may be linked to each other to form a ring structure which may have substituents. ３ * represents the group represented by formula (BT-1). Formula (BT-1) *-Ar Ｂ１ - (L Ｂ１ -Ar Ｂ２ )n Ｂ１ -L Ｂ２ -P Ｂ１ Ar Ｂ１ and Ar Ｂ２ Each of these independently represents a divalent aromatic ring group which may have substituents. Ｂ１ and L Ｂ２ P represents a single bond or a divalent linking group. Ｂ１ n represents a hydrogen atom or a polymerizable group (preferably a group exemplified by polymerizable group P). Ｂ１ This represents a non-negative integer.

[0189] R １ and R ２Examples of monovalent aliphatic hydrocarbon groups represented by include linear or branched alkyl groups having 1 to 20 carbon atoms (e.g., methyl group, ethyl group, iso-propyl group, etc.), cyclic alkyl groups having 3 to 20 carbon atoms (e.g., cyclohexyl group, etc.), and alkenyl groups having 2 to 20 carbon atoms (e.g., vinyl group, etc.). １ and R ２ Examples of monovalent aromatic ring groups represented by include monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms (e.g., phenyl group and naphthyl group), and five-membered or six-membered aromatic heterocyclic groups (heteroatoms included in the ring member atoms constituting the aromatic heterocyclic ring include, for example, nitrogen, oxygen, and sulfur atoms. Specific examples of five-membered or six-membered aromatic heterocyclic groups include, for example, pyridyl group, imidazolyl group, furyl group, piperidyl group, and morpholino group). １ and R ２ Examples of rings that may have substituents and can be formed by linking these rings together include the 4,4,5,5-tetramethyl-1,3,2-dioxaborolane ring.

[0190] In formula (BT), R ３ represents the group represented by the above formula (BT-1). In formula (BT-1), Ar Ｂ１ and Ar Ｂ２ The divalent aromatic ring group represented by R １ and R ２ Examples include groups formed by removing one hydrogen atom from a monovalent aromatic ring group represented by , with a divalent benzene ring group being preferred. Ｂ１ and Ar Ｂ２ The substituents that the divalent aromatic ring group represented by may have are not particularly limited, but examples include alkyl groups (preferably having 1 to 6 carbon atoms). Ｂ１ and L Ｂ２ The divalent linking group represented by is not particularly limited, but for example, -O-, -CO-, -NR Ａ -, -S-, -SO ２ - Examples include divalent aliphatic hydrocarbon groups (which may be linear, branched, or cyclic), and groups formed by combining two or more of these. Ａ R represents a hydrogen atom or substituent.Ａ The substituent represented by is preferably an alkyl group having 1 to 5 carbon atoms (which may be linear, branched, or cyclic). Examples of divalent aliphatic hydrocarbon groups include alkylene groups, alkenylene groups, and alkylylene groups, with alkylene groups being preferred. The number of carbon atoms in the divalent aliphatic hydrocarbon group is preferably 1 to 20, and more preferably 1 to 10. The hydrogen atoms in the above-mentioned divalent aliphatic hydrocarbon group may be substituted with other substituents such as alkoxy groups, cyano groups, nitro groups, and halogen atoms having 2 to 6 carbon atoms.

[0191] L Ｂ１ Examples of divalent linking groups represented by this formula include -COO- and -OCH. ２ -, and -OCH ２ CH ２ Examples include O-, etc. Ｂ２ Examples of divalent linking groups represented by include at least one -CH ２ - is -O-, -CO-, or -NR Ｘ２ Examples include alkylene groups (which may be linear, branched, or cyclic) that may be substituted with -. Ｂ２ A specific example of a divalent linking group represented by -L Ｑ１ -, -OL Ｑ１ -O-, and -O-L Ｑ１ Examples include: L Ｑ１ This represents an alkylene group with 1 to 10 carbon atoms. Ｑ２ This represents an alkylene group or phenylene group having 1 to 8 carbon atoms.

[0192] n Ｂ１ n represents a non-negative integer. Ｂ１ It is preferable that this represents an integer from 1 to 6, and more preferably that it represents an integer from 1 to 4.

[0193] As boronic acid compounds, compounds described in paragraphs

[0026] to

[0029] of Japanese Patent Application Publication No. 2014-129255 can also be preferably used.

[0194] If the composition contains an adhesive, the content of the adhesive is not particularly limited, but it is preferably 0.001 to 10% by mass, and more preferably 0.05 to 3% by mass, relative to the total mass of the liquid crystal compound. The composition may use one type of adhesive alone or two or more types. If two or more types are used, it is preferable that their total content is within the above range.

[0195] [Solvent] The composition may contain a solvent. Preferably, the solvent is capable of dissolving each component of the composition. Examples include methyl ethyl ketone, cyclohexanone, and mixed solvents thereof. When the composition contains a solvent, the amount of solvent in the composition is preferably such that the solid content concentration of the composition is 5 to 50% by mass, and more preferably 10 to 40% by mass. The composition may use one solvent alone or two or more solvents. When two or more solvents are used, it is preferable that their total content is within the above range.

[0196] [Other Ingredients] In addition to the above, the composition may also contain other additives such as antioxidants, ultraviolet absorbers, sensitizers, stabilizers, plasticizers, chain transfer agents, polymerization inhibitors, defoamers, leveling agents, thickeners, flame retardants, dispersants, polymerizable monomers, and colorants such as dyes and pigments.

[0197] [Method for Forming a Cholesteric Liquid Crystal Layer] A cholesteric liquid crystal layer can be formed according to the composition of the present invention. The method for forming a cholesteric liquid crystal layer using the above composition is not particularly limited, and known methods can be employed. An example of a method for forming a cholesteric liquid crystal layer is a method including steps X and Y. If the specific compound has a photoisomerizing group, it is also preferable to include a step Z between steps X and Y in the above method for forming a cholesteric liquid crystal layer. Step X: A step in which a predetermined substrate and the composition are brought into contact to form a composition layer on the substrate. Step Z: A step in which the composition layer is subjected to an exposure treatment to photoisomerize the specific compound. Step Y: A step in which the composition layer is subjected to a photocuring treatment. The procedures of steps X to Z will be described in detail below.

[0198] [Step X] Step X is a step of bringing a substrate and a composition into contact to form a composition layer on the substrate. The type of substrate used is not particularly limited and includes known substrates (e.g., resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates). The method of bringing the substrate and the composition into contact is not particularly limited and includes, for example, coating the composition onto the substrate and immersing the substrate in the composition. After bringing the substrate and the composition into contact, a drying treatment may be performed as needed to remove the solvent from the composition layer on the substrate. Heat treatment may also be performed to promote the orientation of the disc-shaped liquid crystal compound and to create a liquid crystal phase state.

[0199] When the composition layer is subjected to heat treatment, optimal conditions are selected depending on the disc-shaped liquid crystal compound used. In particular, the heating temperature is preferably 25 to 250°C, more preferably 40 to 150°C, and even more preferably 50 to 130°C. The heating time is preferably 0.1 to 60 minutes, and more preferably 0.2 to 5 minutes. Typically, step X can form a composition layer in which the disc-shaped liquid crystal compound is in a cholesteric orientation state.

[0200] [Step Z] Step Z is a step in which the composition layer is exposed to light to photoisomerize a specific compound. In Step Z, the specific compound undergoes photoisomerization in the exposed composition layer, and as a result, the HTP of the composition layer at the exposed location changes. Examples of light used for the exposure treatment include the emission line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light, X-rays, ultraviolet light, and electron beams, with ultraviolet light being preferred. Furthermore, the light used for light irradiation is preferably light with a wavelength of 300 to 400 nm. It is preferable that the specific compound undergoes photoisomerization and a change in HTP occurs as a result of the exposure treatment in Step Y. In this exposure treatment, the degree of change in HTP can also be adjusted by appropriately adjusting the exposure amount and / or exposure wavelength. After exposure, a heat treatment may be performed to further promote the orientation of the disc-shaped liquid crystal compound and to obtain a cholesteric liquid crystal phase. The helical pitch of the liquid crystal phase obtained here reflects the HTP adjusted in the exposure treatment described above.

[0201] [Step Y] Step Y is a step in which the composition layer is subjected to a photocuring treatment. When performing the photocuring treatment of Step Z, it is preferable that the composition contains a photopolymerization initiator. When performing the photocuring treatment of Step Z, it is preferable that the wavelength of the light irradiated in the photocuring treatment is different from the wavelength of the light used in the exposure treatment in Step Y, and it is preferable that the photopolymerization initiator does not show sensitivity to the wavelength of the light used in the exposure treatment in Step Y.

[0202] Examples of light used in the exposure process include the emission spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light, X-rays, ultraviolet light, and electron beams, with ultraviolet light being preferred. Among these, light with a wavelength of 350 nm or more (preferably 350 to 370 nm) is preferred for light irradiation.

[0203] The heat treatment temperature is preferably 40 to 250°C, more preferably 50 to 150°C, and even more preferably 60 to 130°C. The heating time is preferably 0.01 to 60 minutes, and more preferably 0.03 to 5 minutes.

[0204] The cholesteric liquid crystal layer is preferably a layer in which a cholesteric liquid crystal phase is fixed. In the method for forming the cholesteric liquid crystal layer described above, a layer in which a cholesteric liquid crystal phase is fixed can be formed by curing the composition layer. The cholesteric liquid crystal layer does not need to exhibit liquid crystalline properties anymore. More specifically, for example, the most typical and preferred embodiment of the "fixed" state of the cholesteric liquid crystal phase is a state in which the orientation of the liquid crystal compound that constitutes the cholesteric liquid crystal phase is maintained. More specifically, it is preferable that the layer is non-fluid in a temperature range of 0 to 50°C normally, and -30 to 70°C under more severe conditions, and that the fixed orientation can be stably maintained without causing changes in the orientation form due to external fields or external forces.

[0205] [Reflective Film] The cholesteric liquid crystal layer formed by the composition of the present invention (preferably a layer in which a cholesteric liquid crystal phase is fixed) can be applied to various uses, for example, a reflective film. The reflective film can reflect light in a predetermined reflection band.

[0206] [Laminate] The laminate of the present invention comprises a plurality of reflective films of the present invention, or comprises a reflective film of the present invention and a reflective film formed using a rod-shaped liquid crystal compound. The reflective film of the present invention is a cholesteric liquid crystal layer (preferably a layer in which a cholesteric liquid crystal phase is fixed) formed by the composition of the present invention as described above, as previously stated.

[0207] The multiple reflective films forming the laminate and the reflective film formed using the rod-shaped liquid crystal compound may each have different reflection bands, or they may reflect circularly polarized light in different helical directions. By laminating multiple reflective films having different reflection bands, it becomes possible to achieve a wider reflection band, and by laminating reflective films that reflect circularly polarized light in different helical directions, it becomes possible to achieve high reflectivity for natural light containing left and right circularly polarized components.

[0208] The reflective film formed using the rod-shaped liquid crystal compound is typically a cholesteric liquid crystal layer formed by a composition containing the rod-shaped liquid crystal compound and a chiral agent, and more preferably a cholesteric liquid crystal layer formed by a composition containing the rod-shaped liquid crystal compound, a chiral agent, and a polymerization initiator. Known compositions can be used for the cholesteric liquid crystal layer formed by a composition containing the rod-shaped liquid crystal compound and a chiral agent.

[0209] Furthermore, by laminating a reflective film formed from a disc-shaped liquid crystal compound with a reflective film formed from a rod-shaped liquid crystal compound, it becomes possible to bring the phase difference (Rth) in the thickness direction close to zero. This suppresses the decrease in the degree of circular polarization for circularly polarized light incident obliquely on the reflective film, thereby achieving high reflectivity.

[0210] [Compounds] The present invention also relates to compounds (Compound A, Compound B). Compounds A and B of the present invention will be described in detail below.

[0211] [Compound A] The compound of the present invention (Compound A) is a compound represented by formula (1S), and its molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol. －１ ・cm －１The following is the compound in question.

[0212]

[0213] In formula (1S), X １ This represents the base expressed by equation (X-1). Equation (X-1) *-A ｘ１ - (R ｘ１ )n ｘ１ In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ Represents a +1 valent π-conjugated group. R ｘ１ n represents a monovalent substituent. ｘ１ n represents a non-negative integer. ｘ１ If there are two or more, multiple R ｘ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. A ｘ１ If it is a single bond, n ｘ１ represents 1. In equation (1S), Y １ This represents the base expressed by formula (Y-1). Formula (Y-1) *-A ｙ１ - (R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ Represents a +1 valent π-conjugated group. R ｙ１ n represents a monovalent substituent. ｙ１ n represents a non-negative integer. ｙ１ If there are two or more, multiple R ｙ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. A ｙ１ If it is a single bond, n ｙ１ represents 1. In equation (1S), Z １ This represents a base represented by formula (Z-1).

[0214] In formula (Z-1), L ｚ１ is, n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be identical or different from each other. * indicates the bonding position. However, in the above formula (1S), A ｘ１ , A above ｙ１ , and the above L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1S) is satisfied. Equation (W-1S) m ｘ１ +m ｙ１ +m ｚ１ ≥21

[0215] Compound A is a form of the compound represented by formula (1S) described in detail in the upper section, and m ｘ１ +m ｙ１ +m ｚ１ This corresponds to a compound that satisfies the condition ≥ 21. ｘ１ +m ｙ１ +m ｚ１ The composition and preferred embodiments of compound A, other than the value of m, are the same as those of the compound represented by formula (1S) described above. ｘ１ +m ｙ１ +m ｚ１ A value of 22 or higher is even more preferable. ｘ１ +m ｙ１ +m ｚ１ There is no particular upper limit to the value, but it is usually 50 or less, preferably 40 or less, more preferably 30 or less, even more preferably 28 or less, and particularly preferably 26 or less.

[0216] [Compound B] The compound of the present invention (Compound B) is a compound represented by formula (1R), and its molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol. －１ ・cm －１ The following is the compound in question.

[0217]

[0218] In formula (1R), X ２ This represents the base expressed by equation (X-1). Equation (X-1) *-A ｘ１ - (Rｘ１ )n ｘ１ In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ Represents a +1 valent π-conjugated group. R ｘ１ n represents a monovalent substituent. ｘ１ n represents a non-negative integer. ｘ１ If there are two or more, multiple R ｘ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. A ｘ１ If it is a single bond, n ｘ１ represents 1. In equation (1R), Y ２ This represents the base expressed by formula (Y-1). Formula (Y-1) *-A ｙ１ - (R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ Represents a +1 valent π-conjugated group. R ｙ１ n represents a monovalent substituent. ｙ１ n represents a non-negative integer. ｙ１ If there are two or more, multiple R ｙ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. A ｙ１ If it is a single bond, n ｙ１ represents 1. In equation (1R), Z ２ This represents the base expressed by formula (Z-1).

[0219]

[0220] In formula (Z-1), L ｚ１ is, n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１ n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be identical or different from each other. * indicates the bonding position. However, in the above formula (1R), the above A ｘ１ , A aboveｙ１ , and the above L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1R) is satisfied. Equation (W-1R) m ｘ１ +m ｙ１ +m ｚ１ ≥21

[0221] Compound B is a form of the compound represented by formula (1R) described in detail in the upper section, and m ｘ１ +m ｙ１ +m ｚ１ This corresponds to a compound that satisfies the condition ≥ 21. ｘ１ +m ｙ１ +m ｚ１ The composition and preferred embodiments of compound B, other than the value of m, are the same as those of the compound represented by formula (1R) described above. ｘ１ +m ｙ１ +m ｚ１ A value of 22 or higher is even more preferable. ｘ１ +m ｙ１ +m ｚ１ There is no particular upper limit to the value, but it is usually 50 or less, preferably 40 or less, more preferably 30 or less, even more preferably 28 or less, and particularly preferably 26 or less.

[0222] The present invention will be described in more detail below based on the following examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples.

[0223] [Specific Compounds and Comparative Compounds] The specific compounds (compounds represented by formula (1S), which include compounds 1 to 6) and comparative compounds (comparative compounds 1 to 2) used in the examples and comparative examples are shown below.

[0224]

[0225] [Synthesis of Specific Compounds] <Synthesis of Compound 1> Compound 1 was synthesized according to the following scheme. The synthesis procedure for Compound 1 is shown below.

[0226]

[0227] (Synthesis of Intermediate 1) 4.0 g of 4-chloroformylphthalic anhydride (manufactured by Kanto Chemical Co., Ltd.) and 64 mL of dichloromethane (manufactured by Wako Pure Chemical Industries, Ltd.) were placed in a three-necked flask (capacity 200 mL) to obtain a mixture. The mixture was cooled to 0°C, and 0.88 g of ethanol (manufactured by Wako Pure Chemical Industries, Ltd.) and 2.05 g of 2,6-lutidine (manufactured by Wako Pure Chemical Industries, Ltd.) were added dropwise. The temperature was then raised to 20°C and the mixture was stirred for 3 hours. After stirring, 64 mL of ethyl acetate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the resulting solid was filtered off. Intermediate 1 was obtained by removing the solvent from the obtained solution under reduced pressure (4.1 g, yield 97%).

[0228] (Synthesis of Compound 1) Intermediate 1 (1.6 g), toluene (Wako Pure Chemical Industries, Ltd.), triphenylphosphine (Wako Pure Chemical Industries, Ltd.), and thionyl chloride (Wako Pure Chemical Industries, Ltd.) (1.8 mL) were placed in a three-necked flask (capacity 100 mL) to obtain a mixture. The mixture was heated to 110°C and stirred for 5 hours. After stirring, the mixture was cooled to room temperature to obtain a toluene solution of intermediate 2 (3.0 g).

[0229] 3.0 g of (S)-binaphthol (manufactured by Kanto Chemical Co., Ltd.), 30 mL of tetrohydrofuran (THF) (manufactured by Wako Pure Chemical Industries, Ltd.), and 50 mL of N,N-diisopropylethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) were placed in a three-necked flask (capacity 100 mL) to obtain a mixture. The mixture was cooled to 0°C, 3.0 g of toluene solution of intermediate 2 was added dropwise, and the resulting reaction mixture was heated to 20°C and stirred for 2 hours. After stirring, 60 mL of ethyl acetate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 60 mL of water were added, and the organic layer was extracted. The obtained solution was washed with 0.1 N hydrochloric acid solution, saturated baking soda solution, and 10% saline solution, respectively, dried over magnesium sulfate, filtered by Celite, and the solvent was removed by vacuum distillation. The obtained crude product was purified by silica gel column chromatography using acetone / hexane (volume ratio 20:80) as the developing solvent. Compound 1 was obtained by vacuum distillation of the separated solution to obtain compound 1 (85 mg, yield 1.7%). Compound 1１ ¹H NMR (Nuclear Magnetic Resonance) (Deuterated solvent: CDCl) ３ The results of the identification by ) are shown below. 1 H NMR(CDCl3): δ8.63(1H, s), 8.30(1H, dd), 8.03(4H, m), 7.66(1H, d), 7.54(4H, m), 7.41 (1H, m), 7.36 (1H, m), 7.19 (1H, d), 7.07 (1H, d), 4.45 (2H, q), 1.44 (3H, t)

[0230] <Synthesis of Compound 3> Compound 3 was synthesized according to the following scheme. The synthesis procedure for Compound 3 is shown below.

[0231]

[0232] (Synthesis of Intermediate 3) 5.0 g of (S)-binaphthol (manufactured by Kanto Chemical Co., Ltd.) and 50 mL of butyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.) were placed in a three-necked flask (capacity 200 mL) to obtain a mixture. The mixture was cooled to 0°C, and 7.6 g of bromine (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise. The resulting reaction mixture was then stirred for 5 hours. After stirring, the reaction mixture was washed with sodium bisulfite solution (1.7 g of sodium bisulfite (manufactured by Wako Pure Chemical Industries, Ltd.), 25 mL of water), water (25 mL), and sodium bicarbonate solution (1.0 g of sodium bicarbonate (manufactured by Wako Pure Chemical Industries, Ltd.), 25 mL of water). The resulting solutions were dried over magnesium sulfate, and the solvent was removed from the solutions under reduced pressure. The resulting residue, 125 mL of tetrohydrofuran (THF) (manufactured by Wako Pure Chemical Industries, Ltd.), and 3.2 g of phthalate chloride (manufactured by Wako Pure Chemical Industries, Ltd.) were placed in a three-necked flask to obtain a mixture. The mixture was cooled to 0°C, 4.5 g of triethylamine (Wako Pure Chemical Industries, Ltd.) was added dropwise, and the temperature was raised to 20°C and stirred for 1 hour. After stirring, 70 mL of water, 70 mL of methanol (Wako Pure Chemical Industries, Ltd.), and 2 mL of 35% hydrochloric acid solution (Wako Pure Chemical Industries, Ltd.) were added to the reaction mixture, and the resulting solid was filtered off. The filtered solid was air-dried at 40°C for 12 hours to obtain intermediate 3 (5.8 g, yield 58%).

[0233] (Synthesis of Compound 3) 3.00 g of intermediate 3, 30 mL of N,N-dimethylformamide (DMF) (Wako Pure Chemical Industries, Ltd.), 6.0 g of triethylamine (Wako Pure Chemical Industries, Ltd.), and 2.6 g of ethyl acrylate (Wako Pure Chemical Industries, Ltd.) were added to a three-necked flask (capacity 100 mL) to obtain a mixture. After deoxygenating the inside of the three-necked flask, 175 mg of orthotolylphosphine (Wako Pure Chemical Industries, Ltd.) and 70.4 mg of palladium(II) acetate (Wako Pure Chemical Industries, Ltd.) were added to the mixed solution in the three-necked flask, and the mixture was stirred at 90°C for 1 hour. After stirring, the resulting reaction solution was cooled to room temperature, and 90 mL of ethyl acetate (Fujifilm Wako Pure Chemical Industries, Ltd.) and 90 mL of 0.1 N hydrochloric acid solution were added to extract the organic layer. The obtained solution was washed with saturated baking soda water and 10% saline solution, respectively, dried over magnesium sulfate, filtered by Celite, and the solvent was removed by vacuum distillation. The crude product obtained was purified by silica gel column chromatography using ethyl acetate / hexane (volume ratio 25:75) as the developing solvent. Compound 3 was obtained by removing the solvent under reduced pressure from the fractionated solution (2.5 g, yield 78%). １ ¹H NMR (Nuclear Magnetic Resonance) (Deuterated solvent: CDCl) ３ The results of the identification by ) are shown below. 1 H NMR(CDCl3): δ8.03(5H, m), 7.87(2H, d), 7.70(1H, m), 7.58(6H, m), 7.26(1H, d), 7.02(1H, d), 6.55(2H, dd), 4.30(4H, m), 1.36(6H, m)

[0234] <Synthesis of Compounds 2, 4, and 5> Compounds 2, 4, and 5 were synthesized using the method described above.

[0235] <Synthesis of Compound 6> Compound 6 is synthesized by referring to the method described above.

[0236] [Comparative Compounds] Comparative compounds 1 and 2 were synthesized using the method described above.

[0237] [Evaluation 1] [Evaluation of Examples 1-5 and Comparative Examples 1-2] <<Evaluation of Helical Torsional Force (HTP)>> The HTP of the compositions was determined by the following procedure.

[0238] <Preparation of Compositions> Various compositions for evaluation were prepared with the formulations shown below. The amount of each of Compounds 1 to 5, Comparative Compound 1, and Comparative Compound 2 added was appropriately adjusted so that the reflection center wavelength in the liquid crystal layer fabrication described later falls within the range of 500 to 600 nm. ----------------------------------------------------------------- Compounds 1 to 5, comparative compound 1 and comparative compound 2: 2 to 5 parts by mass Liquid crystal compound LC-1 shown below: 40 parts by mass Liquid crystal compound LC-2 shown below: 60 parts by mass Photopolymerization initiator (Irgacure OXE01, manufactured by BASF): 3.0 parts by mass Compound A (orientation control agent): 0.1 parts by mass Compound B (adhesion agent): 3.0 parts by mass Solvent (methyl ethyl ketone): an amount that results in a solid content concentration of 20% by mass of the composition -----------------------------------------------------------------

[0239]

[0240]

[0241]

[0242] <Preparation of Liquid Crystal Layer A> A polyimide alignment film material SE-5811 (manufactured by Nissan Chemical Corporation) was applied to a cleaned glass substrate to form a coating. After firing the obtained coating, an alignment film-attached substrate was prepared by rubbing. 90 μL of the above composition was spin-coated onto the rubbing surface of this alignment film at 1500 rpm for 10 seconds, and then heated and dried at 120°C for 4 minutes to form liquid crystal layer A. Next, in an environment of 120°C with an oxygen concentration of 100 volume ppm or less, 1200 mJ / cm² was treated with a metal halide lamp with wavelengths below 330 nm cut off. ２ The liquid crystal layer A was fixed by exposure to achieve the specified integrated light intensity. It was confirmed that all of the fabricated liquid crystal layer A reflected right-circularly polarized light in the wavelength range of 500-600 nm.

[0243] <HTP Measurement> The transmission spectrum of the obtained liquid crystal layer A was measured at room temperature (23°C) using a spectrophotometer (Shimadzu Corporation, UV-3100 (PC)). The central reflection wavelength was determined from the spectral shape in the visible range (400-700 nm), and the HTP (initial HTP) was calculated according to the following formula: HTP = (average refractive index of the liquid crystal compound) / {(concentration of the chiral compound relative to the liquid crystal compound (mass%)) × (central reflection wavelength)} [μm －１ The calculations were performed assuming that the average refractive index of the liquid crystal compound is 1.55.

[0244] <<Evaluation of Color>> The evaluation of color will be carried out according to the following procedure.

[0245] <Preparation of Liquid Crystal Layer B> A polyimide alignment film material SE-5811 (manufactured by Nissan Chemical Corporation) is applied to a cleaned glass substrate to form a coating. After firing the resulting coating, a substrate with an alignment film is prepared by rubbing. The above composition is applied to the rubbing surface of this alignment film so that the film thickness after drying is 3.5 μm. After application, it is heated and dried at 120°C for 4 minutes to form liquid crystal layer B. Next, in an environment of 120°C with an oxygen concentration of 100 ppm by volume or less, a metal halide lamp with a wavelength cut off below 330 nm is used to irradiate at 1200 mJ / cm². ２ The liquid crystal layer B is fixed by exposing it to such an integrated light intensity.

[0246] <Evaluation of Coloration> Left-polarized light is incident on the fabricated liquid crystal layer B, and the color of the transmitted light is judged visually. Layers without coloration are evaluated as "A," and those with coloration are evaluated as "B." It is preferable that there is no coloration.

[0247] <<Molar extinction coefficient ε(L·mol) at a wavelength of 400 nm －１ ・cm －１ Evaluation of comparative compounds 1 and 2 at a wavelength of 400 nm: ε(L・mol) －１ ・cm －１The molar extinction coefficient ε(L·mol) was determined by the following procedure. A 1 mg / 100 mL tetrahydrofuran solution of each compound was prepared, and the tetrahydrofuran solvent was used as a reference. The absorbance at a wavelength of 400 nm was measured using a spectrophotometer (Shimadzu Corporation, UV-3100 (PC)) and a 10 mm cell, and the molar extinction coefficient ε(L·mol) at a wavelength of 400 nm was determined. －１ ・cm －１ ) was calculated.

[0248] Molar extinction coefficient ε(L·mol) at a wavelength of 400 nm for specific compounds (compounds 1-5) －１ ・cm －１ The same method is used to determine the value of ).

[0249] [Evaluation of Example 6] Using compound 6, various evaluations were performed in the same procedure as in Example 1.

[0250] Table 1 is shown below. Note that the "-" in the table means that there are zero π electrons, not π conjugation.

[0251]

[0252] The composition in the example was found to have a high HTP. On the other hand, the composition in the comparative example was found not to produce the desired effect.

[0253] [Evaluation 2] <Preparation of Liquid Crystal Layer C> Liquid crystal layer C is prepared in the same manner as in the preparation of liquid crystal layer B, except that the composition is changed to the following composition. --------------------------------------------------- Compound 1: 3.3 parts by mass Liquid crystal compound LC-1: 20 parts by mass Liquid crystal compound LC-2: 30 parts by mass Liquid crystal compound LC-3 shown below: 50 parts by mass Photopolymerization initiator (Irgacure OXE01, manufactured by BASF): 3.0 parts by mass Compound A (orientation control agent): 0.1 parts by mass Compound B (adhesion agent): 3.0 parts by mass Solvent (methyl ethyl ketone): an amount such that the solid content concentration of the composition is 20% by mass ---------------------------------------------------

[0254]

[0255] The transmission spectrum of the obtained liquid crystal layer C was measured at room temperature (23°C) using a spectrophotometer (Shimadzu Corporation, UV-3100 (PC)). It was confirmed that liquid crystal layer C has a reflection band in the visible range (400-700 nm), and that its reflection band is wider and its reflectivity is higher than that of liquid crystal layer B in Example 1.

Claims

1. A composition comprising a disk-shaped liquid crystal compound and at least one compound selected from the group consisting of the compound represented by formula (1S) and the compound represented by formula (1R). X in formula (1S) ｚ１ , ２ , ｚ１ , １ , and X in formula (1R) ２ represents a group represented by formula (X-1). Formula (X-1) *-A ｘ１ -(R ｘ１ )n ｘ１ In formula (X-1), A ｘ１ represents a hydrogen atom, a single bond, or an n ｘ１ +1-valent π-conjugated group. R ｘ１ represents a monovalent substituent. n ｘ１ represents an integer of 0 or more. n ｘ１ When n is 2 or more, the plurality of R ｘ１ may be the same as or different from each other. * represents the bonding position. However, when A ｘ１ is a hydrogen atom, n ｘ１ represents 0. When A ｘ１ is a single bond, n ｘ１ represents 1. Y in formula (1S) １ and Y in formula (1R) ２ represents a group represented by formula (Y-1). Formula (Y-1) *-A ｙ１ -(R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ represents a hydrogen atom, a single bond, or an n ｙ１ +1-valent π-conjugated group. R ｙ１ represents a monovalent substituent. n ｙ１ represents an integer of 0 or more. n ｙ１ When n is 2 or more, the plurality of R ｙ１ may be the same as or different from each other. * represents the bonding position. However, when A ｙ１ is a hydrogen atom, n ｙ１ represents 0. When A ｙ１ is a single bond, n ｙ１ represents 1. Z in formula (1S) １ and Z in formula (1R) ２ represents a group represented by formula (Z-1). In formula (Z-1), L ｚ１ is n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１ n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be the same or different from each other. * indicates the bonding position. However, in formula (1S) and formula (1R), A ｘ１ , A ｙ１ , and the L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1) is satisfied. Equation (W-1) m ｘ１ +m ｙ１ +m ｚ１ ≥12 2. The composition according to claim 1, wherein the group represented by formula (Z-1) represents >C=O, >C=S, or the group represented by formula (Za). In equation (Za), Ar ｚａ * represents the group represented by formula (Za1) or the group represented by formula (Za2). * represents the bond position. In formula (Za1), Ar ｚａ１ is, n ｚａ１ Represents a divalent aromatic ring group. L ｚａ１ R represents a single bond or a divalent π-conjugated group. ｚａ１ n represents a monovalent substituent. ｚａ１ n represents a non-negative integer. ｚａ１ If there are two or more, multiple L ｚａ１ R with each other and with multiple Rs ｚａ１ The elements may be the same or different from each other. * indicates the joining position. In formula (Za2), Ar ｚａ２ is, n Ｚａ１ Represents a +2 valent monocyclic aromatic ring group. L ｚａ１ R represents a single bond or a divalent π-conjugated group. ｚａ１ n represents a monovalent substituent. ｚａ１ n represents a non-negative integer. ｚａ１ If there are two or more, multiple L ｚａ１ R with each other and with multiple Rs ｚａ１ The elements may be the same or different from each other. Ｚｂ１ This represents 2 or 3.

3. The composition according to claim 2, wherein the group represented by formula (Za) represents the group represented by formula (Za1-A). Ar ｚａ１１ n ｚａ１ Represents the aromatic ring of the valence. L ｚａ１ R represents a single bond or a divalent π-conjugated group. ｚａ１ n represents a monovalent substituent. ｚａ１ n represents a non-negative integer. ｚａ１ If there are two or more, multiple L ｚａ１ R with each other and with multiple Rs ｚａ１ The elements may be the same or different from each other. * indicates the joining position.

4. The group represented by the formula (X-1) represents a group selected from the group consisting of the group represented by the formula (PX1) and the group represented by the formula (PX2), or the group represented by the formula (Y-1) represents a group selected from the group consisting of the group represented by the formula (PY1) and the group represented by the formula (PY2), the composition according to claim 1. Formula (PX1) *-CR ｘ２ =CR ｘ２ -T ｘａ -T ｘｂ -T ｘｃ In the formula (PX1), R ｘ２ each independently represents a hydrogen atom or a monovalent substituent. T ｘａ represents a single bond, >C=O, or >C=S. T ｘｂ represents a single bond, n ｘ１１ + monovalent aromatic ring group, or n ｘ１１ + monovalent group formed by linking two or more monocyclic aromatic ring groups with a single bond. T ｘｃ is, when T ｘｂ represents a single bond, the group represented by *-R ｘ３ . When T ｘｂ represents n ｘ１１ + monovalent aromatic ring group, or n ｘ１１ + monovalent group formed by linking two or more monocyclic aromatic ring groups with a single bond, it represents the group represented by *-(R ｘ１ )n ｘ１１ . R ｘ１ represents a monovalent substituent. R ｘ３ each independently represents a hydrogen atom or a monovalent substituent. n ｘ１１ represents an integer of 0 or more. * represents the bonding position. Formula (PX2) *-Ar ｘａ -(R ｘ１ )n ｘ１１ In the formula (PX2), Ar ｘａ represents n ｘ１１ + monovalent aromatic ring group, or n ｘ１１ + monovalent group formed by linking two or more monocyclic aromatic ring groups with a single bond. R ｘ１ represents a monovalent substituent. n ｘ１１ represents an integer of 0 or more. * represents the bonding position. Formula (PY1) *-CR ｙ２ =CR ｙ２ -T ｙａ -T ｙｂ -T ｙｃ In formula (PY1), R ｙ２ Each of these independently represents a hydrogen atom or a monovalent substituent. ｙａ T represents a single bond, >C=O, or >C=S. ｙｂ is a single bond, n ｙ１１ +1 valent aromatic ring group, or n ｙ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｙｃ is, T ｙｂ When this represents a single bond, *-R ｙ３ It represents a group represented by T ｙｂ gan ｙ１１ +1 valent aromatic ring group, or n ｙ１１ When representing a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, the expression *-(R ｙ１ )n ｙ１１ Represents the group represented by R. ｙ１ R represents a monovalent substituent. ｙ３ Each of these independently represents a hydrogen atom or a monovalent substituent. ｙ１１ represents a non-negative integer. * represents the join position. Equation (PY2) *-Ar ｙａ - (R ｙ１ )n ｙ１１ In formula (PY2), Ar ｙａ is, n ｙ１１ +1 valent aromatic ring group, or n ｙ１１ This represents a group consisting of two or more monocyclic aromatic ring groups linked by a single bond, with a +1 valency. ｙ１ n represents a monovalent substituent. ｙ１１ represents a non-negative integer. * represents the join position.

5. The molar extinction coefficient at a wavelength of 400 nm in a tetrahydrofuran solution of the compound represented by formula (1S) and the compound represented by formula (1R) is 1000 L·mol. －１ ・cm －１ The composition according to claim 1 or 2, which is as follows:

6. The composition according to claim 1 or 2, wherein the disc-shaped liquid crystal compound comprises a compound represented by formula (5). In formula (5), T １１ , T １２ , and T １３ Each of them independently, -CH ２ = or represents a nitrogen atom. R １１ , R １２ , and R １３ Each of these independently represents a group or hydrogen atom represented by formula (A1). However, R １１ , R １２ , and R １３ At least two of these represent the base represented by formula (A1). *-X １１ - (Y １１ )n-L １１ - Q １１ (A1) In formula (A1), X １１ This represents a divalent aromatic heterocyclic group represented by formulas (X11-1) to (X11-14), or a divalent fused aromatic ring group formed by the fusion of two to three monorings, which may have substituents. １１ represents a divalent aromatic ring group which may have substituents. n represents an integer of 1 or more. L １１ represents a linear or branched alkylene group or alkenylene group, and -CH is present in the alkylene group or alkenylene group. ２ At least one of the following is -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ It may be substituted with -, and at least one of the hydrogen atoms present in the alkylene group and the alkenylene group may be substituted with a halogen atom. Ｔ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. However, the -CH present in the alkylene group and the alkenylene group may also be present. ２ Two or more hyphens are -O-, -CO-O-, -O-CO-O-, -CO-, -S-, -SO ２ -, -NR Ｔ - or -NR Ｔ -SO ２ When replaced with -, adjacent -CH ２ - is never substituted by the aforementioned group. Q １１ X represents a polymerizable group, a hydrogen atom, -OH, -COOH, or a halogen atom. Note that there are multiple X in formula (5). １１ Fellow Y １１ Fellow, L １１ Fellow members, and Q １１ The individuals may be identical or different from one another.

7. The composition according to claim 1 or 2, further comprising a photopolymerization initiator and a solvent.

8. The composition according to claim 1 or 2, further comprising a vertical alignment agent.

9. A reflective film formed using the composition described in claim 1 or 2.

10. A laminate comprising the reflective film described in claim 9 and a reflective film formed using a rod-shaped liquid crystal compound.

11. A compound represented by formula (1S), wherein the molar extinction coefficient of the compound at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol －１ ・cm －１ The following are the compounds. X in equation (1S) １ This represents the base expressed by equation (X-1). Equation (X-1) *-A ｘ１ - (R ｘ１ )n ｘ１ In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ Represents a +1 valent π-conjugated group. R ｘ１ n represents a monovalent substituent. ｘ１ n represents a non-negative integer. ｘ１ If there are two or more, multiple R ｘ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. A ｘ１ If it is a single bond, n ｘ１ represents 1. Y in equation (1S) １ This represents the base expressed by formula (Y-1). Formula (Y-1) *-A ｙ１ - (R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ Represents a +1 valent π-conjugated group. R ｙ１ n represents a monovalent substituent. ｙ１ n represents a non-negative integer. ｙ１ If there are two or more, multiple R ｙ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. A ｙ１ If it is a single bond, n ｙ１ represents 1. Z in equation (1S) １ This represents the base expressed by formula (Z-1). In formula (Z-1), L ｚ１ is, n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１ n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be the same or different from each other. * indicates the bonding position. However, in the above formula (1S), the A ｘ１ , A ｙ１ , and the L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1S) is satisfied. Equation (W-1S) m ｘ１ +m ｙ１ +m ｚ１ ≥21 12. A compound represented by formula (1R), wherein the molar extinction coefficient of the compound at a wavelength of 400 nm in a tetrahydrofuran solution is 1000 L·mol －１ ・cm －１ The following are the compounds. X in equation (1R) ２ This represents the base expressed by equation (X-1). Equation (X-1) *-A ｘ１ - (R ｘ１ )n ｘ１ In formula (X-1), A ｘ１ is a hydrogen atom, a single bond, or n ｘ１ Represents a +1 valent π-conjugated group. R ｘ１ n represents a monovalent substituent. ｘ１ n represents a non-negative integer. ｘ１ If there are two or more, multiple R ｘ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｘ１ If n is a hydrogen atom, ｘ１ represents 0. A ｘ１ If it is a single bond, n ｘ１ represents 1. Y in equation (1R) ２ This represents the base expressed by formula (Y-1). Formula (Y-1) *-A ｙ１ - (R ｙ１ )n ｙ１ In formula (Y-1), A ｙ１ is a hydrogen atom, a single bond, or n ｙ１ Represents a +1 valent π-conjugated group. R ｙ１ n represents a monovalent substituent. ｙ１ n represents a non-negative integer. ｙ１ If there are two or more, multiple R ｙ１ The elements may be identical or different from each other. * indicates the joining position. However, A ｙ１ If n is a hydrogen atom, ｙ１ represents 0. A ｙ１ If it is a single bond, n ｙ１ represents 1. Z in equation (1R) ２ This represents the base expressed by formula (Z-1). In formula (Z-1), L ｚ１ is, n ｚ１ Represents a +2 valent π-conjugated group. R ｚ１ n represents a monovalent substituent. ｚ１ n represents a non-negative integer. ｚ１ If there are two or more, multiple R ｚ１ The elements may be identical or different from each other. * indicates the bonding position. However, in formula (1R), the A ｘ１ , A ｙ１ , and the L ｚ１ The number of π electrons contained in each is m. ｘ１ , m ｙ１ , and m ｚ１ When this is the case, the following relationship (W-1R) is satisfied. Equation (W-1R) m ｘ１ +m ｙ１ +m ｚ１ ≥21

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