Chalcone derivative, composition, optical film and method for producing them

Abstract

To provide an optical film, especially, a compound constituting a retardation film.SOLUTION: A chalcone derivative is represented by the following chemical formula (1). In the chemical formula (1), Ar1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed ring type aromatic ring and an aliphatic hydrocarbon ring, which contain an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom as a ring constituent atom, and the monocyclic aromatic ring, the polycyclic aromatic ring, the condensed ring type aromatic ring and the aliphatic hydrocarbon ring may have a substituent. A1, A2, A3, A4, A5 and A6 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed ring type aromatic ring and an aliphatic hydrocarbon ring, which contain an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom as a ring constituent atom, and the monocyclic aromatic ring, the polycyclic aromatic ring, the condensed ring type aromatic ring and the aliphatic hydrocarbon ring may have a substituent.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a chalcone derivative, a composition, an optical film, and methods for producing the same. [Background technology]

[0002] Organic electroluminescence displays and liquid crystal displays are important display devices in our multimedia society and are widely used in various smart devices, computer monitors, televisions, etc. In addition, many optical films are used in these displays to improve their display characteristics, and they play an important role in improving contrast when viewed from the front or at an angle, compensating for color tones, etc.

[0003] Retardation films are optical films used in organic electroluminescence (EL) displays and liquid crystal displays.

[0004] The retardation film can be produced, for example, by dissolving a liquid crystal compound in a solvent, applying a coating liquid obtained on a support substrate on which an alignment film has been formed, and then polymerizing the liquid. Currently, as liquid crystal compounds for retardation films, for example, nematic liquid crystal compounds having a rod-like structure in which 2 to 4 six-membered rings are connected, are known.

[0005] In addition, the retardation film is considered to be suitable for polarization conversion in the entire wavelength region, and it is known that, in theory, uniform polarization conversion is possible in a wavelength region showing the inverse wavelength dispersion of [Re(450 nm) / Re(550 nm)]< 1. A liquid crystal compound capable of forming such a retardation film is disclosed in, for example, Patent Document 1.

[0006] Coating-type optical films can be obtained by a method in which a coating liquid obtained by dissolving a liquid crystal compound in a solvent is applied to a supporting substrate to form a coating film, the polymerizable liquid crystal compound contained in the coating film is transferred to a liquid crystal phase state such as a nematic phase, and the coating film is dried to evaporate off the solvent (e.g., Patent Document 2). [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Patent Publication No. 2011-207765 [Patent Document 2] Patent No. 4606195 Summary of the Invention [Problem to be solved by the invention]

[0008] As described above, the coating type optical film can be obtained by dissolving a liquid crystal compound in a solvent, applying a coating liquid obtained by dissolving the liquid crystal compound in a solvent onto a support substrate to form a coating film, then transferring the polymerizable liquid crystal compound contained in the coating film to a liquid crystal phase state such as a nematic phase, and drying the coating film to remove the solvent. In addition, when the liquid crystal compound used has a portion that exhibits reverse wavelength dispersion, an optical film that exhibits reverse wavelength dispersion retardation can be produced.

[0009] However, only a very small number of compounds, such as 2-(4,7-disubstituted-1,3-benzodithiol-2-ylidene)malononitrile derivatives, have been reported as having a structure in which the moiety that exhibits reverse wavelength dispersion is arranged perpendicular to the long axis direction of the molecule. At present, there are no reports of molecules in which, for example, chalcone derivatives are arranged perpendicular to the long axis direction of the liquid crystal molecule.

[0010] Under these circumstances, the present inventors focused on chalcone derivatives and conducted research with the aim of providing a compound for forming an optical film, particularly a retardation film, by arranging this structure perpendicular to the long axis direction of the molecule. [Means for solving the problem]

[0011] Means for Solving the Problems The present inventors have conducted extensive research to solve the above problems, and as a result have found that, by arranging a chalcone derivative such as cinnamoylthiophene perpendicular to the long axis direction of the molecule, a chalcone derivative that has a simple structure but can be used as a raw material for optical films, particularly retardation films.

[0012] The present invention has been proposed based on these findings, and specifically has the following configuration. [1] A chalcone derivative represented by the following chemical formula (1).

[0013] [ka]

[0014] [In the above chemical formula (1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L10 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 and Fg 2 may be the same or different and represent a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0015] [ka]

[0016] [In the above chemical formula (Z1), Ar 2represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. [2] The chalcone derivative according to [1], represented by the following chemical formula (1').

[0017] [ka]

[0018] [In the above chemical formula (1'), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0019] [ka]

[0020] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. [3] Ar1 is a ring selected from the group consisting of monocyclic aromatic rings and polycyclic aromatic rings, the ring constituent atoms of which are selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms (these monocyclic aromatic rings and polycyclic aromatic rings may have a substituent). [4] Ar 1 The chemical formula is as follows (Ar 1 -1)~(Ar 1 The chalcone derivative according to any one of [1] to [3], which has a structure represented by the following formula:

[0021] [ka]

[0022] [The above-mentioned chemical formula (Ar 1 -1)~(Ar 1 -7) Medium, X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms. R 4 represents an alkyl group having 1 to 10 carbon atoms. ** represents Ar in the above chemical formula (1). 1 represents the bonding position with other moieties, excluding [5] The chalcone derivative according to any one of [1] to [4], which is represented by the following chemical formula (1-2):

[0023] [ka]

[0024] [In the above chemical formula (1-2), A 1 , A 2 and A3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. [6] A 1 and A 4 The chalcone derivative according to any one of [1] to [5], wherein [7] A method for producing a chalcone derivative represented by the following chemical formula (1'), comprising a step of condensing a dihydroxy compound represented by the following chemical formula (2) with a compound represented by the following chemical formula (3):

[0025] [ka]

[0026] [In the above chemical formula (2), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Fg 3 represents a hydroxy group, a carboxy group, or an amino group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0027] [ka]

[0028] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0029] [ka]

[0030] [In the above chemical formula (3), A 1 , A 2 , and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. Fg 1 represents a hydrogen atom or a polymerizable group. R 2 , and R 3may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 4 represents a hydroxy group, a carboxy group, or a chlorocarbonyl group.

[0031] [ka]

[0032] [In the above chemical formula (1'), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , and A 3 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0033] [ka]

[0034] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. [8] Fg of the dihydroxy compound represented by the above chemical formula (2) 3 is a hydroxy group, and Fg of the compound represented by the above chemical formula (3) 4 is a carboxy group or a chlorocarbonyl group, and L of the chalcone derivative represented by the above chemical formula (1') 1The method for producing a chalcone derivative according to [7], wherein [9] A polymer containing the structure represented by the following chemical formula (P1) as a repeating unit.

[0035] [ka]

[0036] [In the above chemical formula (P1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. R 5 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). X 14 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z2).

[0037] [ka]

[0038] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0039] [ka]

[0040] [In the above chemical formula (Z2), R 6 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.

[10] A composition comprising the chalcone derivative according to any one of [1] to [6].

[11] An optical film comprising the chalcone derivative according to any one of [1] to [6].

[1211] An optical film comprising the polymer according to [9].

[13] The optical film according to

[11] or

[12] , wherein the retardation (Re) measured using a 589 nm light source and represented by the following formula (A) is 1 nm or more.

[0041] Re = (ny-nx) × d (A) [In formula (A), nx represents the refractive index in the fast axis direction in the film plane, ny represents the refractive index in the slow axis direction in the film plane, and d represents the film thickness.]

[14] The optical film according to any one of

[11] to

[13] , wherein a retardation (Re) satisfies the following formula (I): Re(450)≦Re(550) (I) (In formula (I), Re(450) represents an in-plane retardation value measured at a wavelength of 450 nm, and Re(550) represents an in-plane retardation value measured at a wavelength of 550 nm.)

[15] A polarizing plate comprising the optical film according to any one of

[11] to

[14] .

[16] An optical display comprising the polarizing plate according to

[15] .

[17] A method for producing an optical film, comprising the step of applying the composition according to

[10] . Effect of the Invention

[0042] According to the present invention, it is possible to provide a chalcone derivative, a composition, an optical film, and a method for producing the same that can be used as a raw material for an optical film, particularly a retardation film. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0043] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments and specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "from" or "to" means a range including the numerical values ​​before and after "from" or "to" as the lower and upper limits.

[0044] In this specification, the bonding direction of the exemplified divalent groups and chemical structures (e.g., ester bonds or repeating units in a polymer structure) is not particularly limited within the range that is chemically permissible, unless the bonding position is clearly specified.

[0045] The cyclohexane rings described in the specification may be in either the trans or cis configuration, but are preferably in the trans configuration. [Chalcone derivatives] A chalcone derivative according to one embodiment of the present invention is represented by the following chemical formula (1) (hereinafter, may be referred to as the chalcone derivative of the present invention).

[0046] [ka]

[0047] [In the above chemical formula (1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 and Fg 2may be the same or different and represent a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0048] [ka]

[0049] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. In the above chemical formula (1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0050] Here, examples of the substituent in the monocyclic aromatic ring, polycyclic aromatic ring, condensed aromatic ring, and aliphatic hydrocarbon ring include an alkyl group having 1 to 8 carbon atoms, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an acyl group having 2 to 4 carbon atoms.

[0051] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0052] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0053] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0054] Examples of the acyl group having 2 to 4 carbon atoms include an acetyl group, a propionyl group, and a butyryl group.

[0055] Examples of the monocyclic aromatic ring in Ar which has an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom and which may have a substituent include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a pyrrole ring, an imidazole ring, a thiophene ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, and a triazole ring.

[0056] Ar 1 Examples of the polycyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom, which may have a substituent, include a biphenyl ring, a terphenyl ring, a bipyridine ring, a bithiophene ring, and a bifuran ring.

[0057] Ar 1Examples of the fused aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, a benzofuran ring, a benzimidazole ring, a benzothiophene ring, an indole ring, an indazole ring, a benzoxazole ring, a benzothiazole ring, and a benzotriazole ring.

[0058] Ar 1 Examples of the optionally substituted aliphatic hydrocarbon ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a cyclopentane ring, a cyclohexane ring, a tricyclo[5.2.1.0(2,6)]decane ring, and a decahydronaphthalene ring.

[0059] Ar 1 In terms of availability, the aromatic ring is preferably a monocyclic aromatic ring, which may have a substituent and has an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The aromatic ring is more preferably a benzene ring, a furan ring, a thiophene ring, a thiazole ring, or an oxazole ring, in terms of the chalcone derivative of the present invention exhibiting good optical properties, and is particularly preferably a benzene ring or a thiophene ring, in terms of the chalcone derivative of the present invention exhibiting good optical properties.

[0060] Ar 1 Preferred examples of the compound represented by the following formula (Ar 1 -1) to (Ar 1 -7) is an example of the structure shown in

[0061] [ka]

[0062] [The above-mentioned chemical formula (Ar 1 -1)~(Ar 1 -7) Medium, X 6 , X 7 , X 8, X 9 , X 10 , X 11 , X 12 , and X 13 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms. R 4 represents an alkyl group having 1 to 10 carbon atoms. ** indicates Ar in the above chemical formula (1). 1 represents the bonding position with other moieties, excluding (Ar 1 -1)~(Ar 1 -7) X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms.

[0063] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0064] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0065] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0066] Examples of the alkylthio group having 1 to 6 carbon atoms include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.

[0067] Examples of the dialkylamino group having 2 to 8 carbon atoms include a dimethylamino group, a diethylamino group, a dipropylamino group, and a dibutylamino group.

[0068] X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 In terms of excellent optical properties, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom is preferable, and a hydrogen atom, a methyl group, a methoxy group, or a halogen atom is particularly preferable in terms of ease of introduction.

[0069] (Ar 1 -1)~(Ar 1 -7) In R 4 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.

[0070] R 4 In terms of providing excellent optical properties to the polymer of the present invention, a hydrogen atom, a methyl group, or an alkyl group having 1 to 4 carbon atoms is preferred, and a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group is particularly preferred.

[0071] In the above chemical formula (1), A 1 , A2 , A 3 , A 4 , A 5 and A 6 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0072] Here, examples of the substituent in the monocyclic aromatic ring, polycyclic aromatic ring, condensed aromatic ring, and aliphatic hydrocarbon ring include an alkyl group having 1 to 8 carbon atoms, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an acyl group having 2 to 4 carbon atoms.

[0073] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0074] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0075] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0076] Examples of the acyl group having 2 to 4 carbon atoms include an acetyl group, a propionyl group, and a butyryl group.

[0077] A 1 , A 2 , A 3 , A 4 , A 5 and A 6Examples of the monocyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a pyrrole ring, an imidazole ring, a thiophene ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, and a triazole ring.

[0078] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Examples of the polycyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom, which may have a substituent, include a biphenyl ring, a terphenyl ring, a bipyridine ring, a bithiophene ring, and a bifuran ring.

[0079] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Examples of the fused aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, a benzofuran ring, a benzimidazole ring, a benzothiophene ring, an indole ring, an indazole ring, a benzoxazole ring, a benzothiazole ring, and a benzotriazole ring.

[0080] A 1 , A 2 , A 3 , A 4 , A 5 and A 6Examples of the optionally substituted aliphatic hydrocarbon ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a cyclopentane ring, a cyclohexane ring, a tricyclo[5.2.1.0(2,6)]decane ring, and a decahydronaphthalene ring.

[0081] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 As the ring, a cyclohexane ring is preferred in that the chalcone derivative of the present invention exhibits good optical properties.

[0082] Preferred examples of the cyclohexane ring include the following structures, which are preferred in that the chalcone derivative of the present invention exhibits good optical properties (A 1 -1) is preferred.

[0083] [ka]

[0084] (*** indicates the bond position.) In the above chemical formula (1), a2, a3, a5, and a6 each independently represent an integer of 0 to 2.

[0085] In the above chemical formula (1), L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-.

[0086] R 1represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0087] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 Examples of the optionally substituted alkylene group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, an oxymethylene group, an oxyethylene group, an oxytrimethylene group, a methylenedioxy group, or an ethylenedioxy group.

[0088] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 In terms of ease of introduction, the alkylene group is preferably a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, or -NR 1 -C(=O)- is preferred, and a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, or -C(=O)O- is more preferred.

[0089] In the above chemical formula (1), Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-.

[0090] R2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0091] Sp 1 and Sp 2 In the above, examples of the alkylene group having 1 to 20 carbon atoms include structures represented by the following chemical formulas (Sp-1-1) to (Sp-6-20) (the hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 may be substituted with -C(=O)-. 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms).

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the above chemical formula (1), Fg 1 and Fg 2 may be the same or different and represent a hydrogen atom or a polymerizable group.

[0099] Fg 1 and Fg 2 In the above, examples of the polymerizable group include structures shown in the following chemical formulas (Fg-1) to (Fg-24).

[0100] [ka]

[0101] Fg 1 and Fg 2 As the group, a hydrogen atom or the above formula (Fg-1) or (Fg-2) is preferred because of ease of introduction.

[0102] In the above chemical formula (1), X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the above chemical formula (Z1).

[0103] X 1 , X 2 , X 3 , X 4 and X 5 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0104] X 1 , X 2 , X 3 , X 4 and X 5In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0105] X 1 , X 2 , X 3 , X 4 and X 5 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0106] In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0107] Ar 2 As for Ar 1 The following structures are also shown:

[0108] In the above chemical formula (Z1), Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0109] Xz 1 and Xz 2 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0110] Xz 1 and Xz 2In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0111] Xz 1 and Xz 2 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0112] X 1 , X 2 , X 3 , X 4 and X 5 In terms of ease of introduction, a hydrogen atom, a methyl group, or an ethyl group is preferred as the alkyl group.

[0113] A preferred example of the chalcone derivative of the present invention represented by chemical formula (1) is a chalcone derivative represented by the following chemical formula (1'), and a particularly preferred example is a chalcone derivative represented by the following chemical formula (1-2).

[0114] [ka]

[0115] [In the above chemical formula (1'), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , and A 3each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0116] [ka]

[0117] [In the above chemical formula (1-2), A 1 , A 2 and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. Ar in formula (1') 1 , A 1 , A 2 , A 3 , a2, a3, L 1 , L 2 , L 3 , L 4 , L 5 , R 1 , Sp 1 , R 2 , R 3 , Fg 1 , X 1 , X 2 , X 3 , X 4 and X 5 As the Ar of the chemical formula (1), 1 , A 1 , A 2 , A 3 , a2, a3, L 1 , L 2 , L 3 , L 4 , L 5 , R 1 , Sp 1 , R 2 , R 3 , Fg 1 , X 1 , X 2 , X 3 , X 4 and X 5 The same can be mentioned.

[0118] A in chemical formula (1-2) 1 , A 2 , A 3 , a2, a3, L 2 , L 3 , L 4 , L 5 , R 1 , Sp 1 , R 2 , R 3 , Fg 1 , X 1 , X 2 , X 3 , X 4 and X5 As the A in chemical formula (1), 1 , A 2 , A 3 , a2, a3, L 2 , L 3 , L 4 , L 5 , R 1 , Sp 1 , R 2 , R 3 , Fg 1 , X 1 , X 2 , X 3 , X 4 and X 5 The same can be mentioned.

[0119] Preferred examples of the chalcone derivatives of the present invention represented by chemical formula (1) include chalcone derivatives in which a central unit represented by any one of the following chemical formulas (1A-1-1) to (1A-6-7) is combined with a side chain unit represented by any one of the following chemical formulas (1B-1-1) to (1B-4-8). (The * in the structures of the central unit represented by any one of the (1A-1-1) to (1A-6-7) and the side chain unit represented by any one of the (1B-1-1) to (1B-4-8) indicates the bonding position between the central unit and the side chain unit. When there are two * in the structure of the central unit represented by any one of the (1A-1-1) to (1A-6-7), two different ones of the side chain units represented by any one of the (1B-1-1) to (1B-4-8) may be combined.)

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] Among the chalcone derivatives combining the central units represented by the above chemical formulas (1A-1-1) to (1A-6-8) with the side chain units represented by the above chemical formulas (1B-1-1) to (1B-4-8), the combination of the central units (1A-2-1) to (1A-6-6) and the side chain units (1B-2-1) to (1B-4-8) is preferred, and the combination of the central units (1A-4-1) to (1A-4-6) and the side chain units (1B-4-1) to (1B-4-8) is more preferred.

[0128] [ka]

[0129] [ka]

[0130] [ka]

[0131] [ka]

[0132] [ka]

[0133] [ka]

[0134] When the chalcone derivative of the present invention is a liquid crystal compound, its liquid crystal phase transition temperature is low. In particular, the liquid crystal phase transition temperature is preferably 80 to 155° C., more preferably 80 to 150° C., and even more preferably 80 to 145° C. When the nematic phase transition temperature is within the above range, excessive waste of thermal energy can be suppressed, and at the same time, deformation due to heat of the support substrate on which the coating liquid containing the chalcone derivative of the present invention is applied can be suppressed, so that the selectivity of the support substrate can be expanded. [Method of producing chalcone derivatives] The method for producing a chalcone derivative represented by chemical formula (1') of the present invention is a method including a step of condensing a compound represented by the following chemical formula (2) with a compound represented by the following chemical formula (3) (hereinafter, this method may be referred to as the method for producing a chalcone derivative of the present invention). This method is also included in one aspect of the present invention.

[0135] [ka]

[0136] [In the above chemical formula (2), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Fg 3 represents a hydroxy group, a carboxy group, or an amino group. X 1 , X 2 , X 3 , X 4 and X5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0137] [ka]

[0138] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. [In the above chemical formula (3), A 1 , A 2 , and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. Fg 1 represents a hydrogen atom or a polymerizable group. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 4 represents a hydroxy group, a carboxy group, or a chlorocarbonyl group. In the above chemical formula (1'), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Fg 1 represents a hydrogen atom or a polymerizable group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1).

[0139] [ka]

[0140] [In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. In chemical formula (2), Ar 1represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0141] Ar 1 As the Ar 1 The following structure can be mentioned:

[0142] In chemical formula (2), Fg 3 represents a hydroxy group, a carboxy group, or an amino group.

[0143] In chemical formula (2), X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the above chemical formula (Z1).

[0144] X 1 , X 2 , X 3 , X 4 and X 5 As the X in the above chemical formula (1), 1 , X 2 , X 3 , X 4 and X 5 The following structure can be mentioned:

[0145] In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0146] Ar2 As for Ar 1 The following structures are also shown:

[0147] In the above chemical formula (Z1), Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0148] Xz 1 and Xz 2 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0149] Xz 1 and Xz 2 In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0150] Xz 1 and Xz 2 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0151] X 1 , X 2 , X 3 , X 4 and X 5 In terms of ease of introduction, a hydrogen atom, a methyl group, or an ethyl group is preferred as the alkyl group.

[0152] Specific examples of the compound represented by chemical formula (2) include structures represented by the following chemical formulas (2-1-1) to (2-7-4).

[0153] [ka]

[0154] [ka]

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] As the compound represented by the chemical formula (2), the above chemical formulas (2-2-1) to (2-2-11) are preferred.

[0161] In chemical formula (3), A 1 , A 2 and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0162] A 1 , A 2 and A3 As the above, A in the chemical formula (1) 1 , A 2 and A 3 The following structure can be mentioned:

[0163] In chemical formula (3), L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 -C(=O)-, R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0164] L 2 , L 3 , L 4 and L 5 As the group, L in the above chemical formula (1) 2 , L 3 , L 4 and L 5 The following structure can be mentioned:

[0165] In chemical formula (3), Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 may be substituted with -C(=O)-, R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0166] Sp 1 As the compound represented by the above chemical formula (1), 1 The following structure can be mentioned:

[0167] In chemical formula (3), Fg 1 represents a hydrogen atom or a polymerizable group.

[0168] Fg 1 As the Fg 1 The following structure can be mentioned:

[0169] In chemical formula (3), Fg 4 represents a hydroxy group, a carboxy group, or a chlorocarbonyl group.

[0170] The compound represented by the chemical formula (3) may be prepared according to known methods or general organic synthesis methods.

[0171] Specific examples of the compound represented by chemical formula (3) include structures represented by the following chemical formulas (3-1-1-0) to (3-2-4-8).

[0172] [ka]

[0173] [ka]

[0174] [ka]

[0175] [ka]

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] Among the structures represented by the above chemical formulas (3-1-1-0) to (3-2-4-8), (3-1-2-1) to (3-2-4-8) are preferred because the chalcone derivatives of the present invention have good optical properties.

[0181] In the chemical formula (1'), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0182] Ar 1 As the Ar 1 The following structure can be mentioned:

[0183] In the chemical formula (1'), A 1 , A 2 and A 3 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0184] A 1 , A 2 and A 3 As the above, A in the chemical formula (1) 1 , A 2 and A 3The following structure can be mentioned:

[0185] In the chemical formula (1'), L 1 , L 2 , L 3 , L 4 and L 5 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 -C(=O)-, R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0186] L 1 , L 2 , L 3 , L 4 and L 5 As the group, L in the above chemical formula (1) 1 , L 2 , L 3 , L 4 and L 5 The following structure can be mentioned:

[0187] In the chemical formula (1'), Sp 1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 may be substituted with -C(=O)-, R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0188] Sp 1 As the compound represented by the above chemical formula (1), 1 The following structure can be mentioned:

[0189] In chemical formula (1'), Fg 1represents a hydrogen atom or a polymerizable group.

[0190] Fg 1 As the Fg 1 The following structure can be mentioned:

[0191] In the chemical formula (1'), X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the above chemical formula (Z1).

[0192] X 1 , X 2 , X 3 , X 4 and X 5 As the X in the above chemical formula (1), 1 , X 2 , X 3 , X 4 and X 5 The following structure can be mentioned:

[0193] In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0194] Ar 2 As for Ar 1 The following structures are also possible:

[0195] In the above chemical formula (Z1), Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0196] Xz 1 and Xz 2 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0197] Xz 1 and Xz 2 In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0198] Xz 1 and Xz 2 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0199] X 1 , X 2 , X 3 , X 4 and X 5 In terms of ease of introduction, a hydrogen atom, a methyl group, or an ethyl group is preferred as the alkyl group.

[0200] Preferred examples of the chalcone derivative of the present invention represented by chemical formula (1') include those having the same structure as the preferred examples of chemical formula (1).

[0201] L 1 The chalcone derivative represented by (1') in which is -C(=O)O- is Fg 3 A compound represented by the formula (2) in which Fg is a hydroxy group. 4 It can be produced by condensing a compound represented by chemical formula (3), in which

[0202] L 1In producing a chalcone derivative represented by (1') in which Fg 3 A compound represented by the formula (2) in which Fg is a hydroxy group. 4 When a compound represented by chemical formula (3) in which is a carboxy group is used as a substrate, the condensation can be carried out using a condensing agent.

[0203] Examples of the condensation agent include 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, N,N'-diisopropylcarbodiimide, N,N'-dicyclohexylcarbodiimide, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide-p-toluenesulfonate, N,N'-di-tert-butylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide=methiodide, (benzotriazole- (1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, or 4-[[[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy](dimethylamino)methylene]morpholinium hexafluorophosphate can be mentioned.

[0204] When a condensing agent is used, a base may be used to promote the reaction.

[0205] The base may, for example, be an organic base.

[0206] Examples of organic bases include triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, pyrrolidine, morpholine, N-methylmorpholine, imidazole, and N-methylimidazole.

[0207] L 1 In producing a chalcone derivative represented by (1') in which Fg 3 A compound represented by the formula (2) in which Fg is a hydroxy group. 4 When a compound represented by chemical formula (3) in which is a chlorocarbonyl group is used as a substrate, the condensation can be carried out in the presence of a base.

[0208] The base used may be, for example, an organic base, an inorganic base, an organometallic compound, a metal alkoxide, or a metal amide.

[0209] Examples of organic bases include triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, pyrrolidine, morpholine, N-methylmorpholine, imidazole, and N-methylimidazole.

[0210] Examples of inorganic bases include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, and potassium hydride.

[0211] The organometallic compound may, for example, be n-butyllithium, sec-butyllithium, tert-butyllithium, or phenyllithium.

[0212] Metal alkoxides include, for example, sodium methoxide, sodium ethoxide, sodium tert-butoxide, or potassium tert-butoxide.

[0213] Examples of metal amides include lithium amide, sodium amide, lithium diisopropylamide, lithium hexamethyldisilazide, sodium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0214] Among bases, organic bases or inorganic bases are preferred in that the reaction proceeds favorably and is inexpensive, and triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, piperidine, piperazine, pyrrolidine, sodium hydrogencarbonate, or potassium hydrogencarbonate is more preferred.

[0215] The amount of the base used is not particularly limited, and an excess amount may be used.

[0216] Depending on its nature, the base may be used as it is in the form of a solid such as a liquid, grain, granule or powder. Furthermore, solutions of these substances can also be used, and there is no particular limitation on their concentrations.

[0217] An organic solvent can be used during the condensation, and any organic solvent that does not harm the reaction can be used, for example, ether solvents such as diethyl ether, diisopropyl ether, cyclopentyl methyl ether, dimethoxyethane, tetrahydrofuran, etc., aromatic solvents such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, etc., halogen-based solvents such as dichloromethane, chloroform, carbon tetrachloride, etc. These solvents may be used alone or in combination of two or more kinds at any ratio.

[0218] The chalcone derivative of the present invention represented by chemical formula (1') obtained by the method for producing the chalcone derivative of the present invention may be purified to a suitable purity. Examples of the purification method include washing, column chromatography, reprecipitation, and recrystallization.

[0219] Furthermore, among the chalcone derivatives of the present invention represented by chemical formula (1'), those having two different side chain units can be synthesized by reacting two types of compound (2) with compound (3) simultaneously or sequentially. [polymer] A polymer according to one embodiment of the present invention is a polymer containing a structure represented by the following chemical formula (P1) as a repeating unit (hereinafter, may be referred to as a polymer of the present invention).

[0220] [ka]

[0221] [In the above chemical formula (P1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A 1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-. R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-. R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. R 5 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). X 14 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z2).

[0222] [ka]

[0223] [In the above chemical formula (Z1), Ar 2represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0224] [ka]

[0225] [In the above chemical formula (Z2), R 6 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group. In the above chemical formula (P1), Ar 1 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0226] Here, examples of the substituent in the monocyclic aromatic ring, polycyclic aromatic ring, condensed aromatic ring, and aliphatic hydrocarbon ring include an alkyl group having 1 to 8 carbon atoms, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an acyl group having 2 to 4 carbon atoms.

[0227] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0228] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0229] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0230] Examples of the acyl group having 2 to 4 carbon atoms include an acetyl group, a propionyl group, and a butyryl group.

[0231] Ar 1 Examples of the monocyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a pyrrole ring, an imidazole ring, a thiophene ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, and a triazole ring.

[0232] Ar 1 Examples of the polycyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom, which may have a substituent, include a biphenyl ring, a terphenyl ring, a bipyridine ring, a bithiophene ring, and a bifuran ring.

[0233] Ar 1 Examples of the fused aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, a benzofuran ring, a benzimidazole ring, a benzothiophene ring, an indole ring, an indazole ring, a benzoxazole ring, a benzothiazole ring, and a benzotriazole ring.

[0234] Ar 1Examples of the optionally substituted aliphatic hydrocarbon ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a cyclopentane ring, a cyclohexane ring, a tricyclo[5.2.1.0(2,6)]decane ring, and a decahydronaphthalene ring.

[0235] Ar 1 In terms of availability, the aromatic ring is preferably a monocyclic aromatic ring, which may have a substituent and has an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The aromatic ring is more preferably a benzene ring, a furan ring, a thiophene ring, a thiazole ring, or an oxazole ring, in terms of the chalcone derivative of the present invention exhibiting good optical properties, and is particularly preferably a benzene ring or a thiophene ring, in terms of the chalcone derivative of the present invention exhibiting good optical properties.

[0236] Ar 1 Preferred examples of the compound represented by the following formula (Ar 1 -1) to (Ar 1 -7) is an example of the structure shown in

[0237] [ka]

[0238] [The above-mentioned chemical formula (Ar 1 -1)~(Ar 1 -7) Medium, X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms. R 4 represents an alkyl group having 1 to 10 carbon atoms. ** indicates Ar in the above chemical formula (P1). 1 represents the bonding position with other moieties, excluding (Ar 1 -1)~(Ar 1 -7) X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms.

[0239] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0240] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0241] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0242] Examples of the alkylthio group having 1 to 6 carbon atoms include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.

[0243] Examples of the dialkylamino group having 2 to 8 carbon atoms include a dimethylamino group, a diethylamino group, a dipropylamino group, and a dibutylamino group.

[0244] X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , and X 13 In terms of providing excellent optical properties to the polymer of the present invention, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom is preferred, and in terms of ease of introduction, a hydrogen atom, a methyl group, a methoxy group, or a halogen atom is particularly preferred.

[0245] (Ar 1 -1)~(Ar 1 -7) In R 4 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.

[0246] R 4 In terms of providing excellent optical properties to the polymer of the present invention, a hydrogen atom, a methyl group, or an alkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group is particularly preferable.

[0247] In the above chemical formula (P1), A 1 , A 2 , A 3 , A 4 , A 5 and A 6 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0248] Here, examples of the substituent in the monocyclic aromatic ring, polycyclic aromatic ring, condensed aromatic ring, and aliphatic hydrocarbon ring include an alkyl group having 1 to 8 carbon atoms, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an acyl group having 2 to 4 carbon atoms.

[0249] Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0250] Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0251] Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0252] Examples of the acyl group having 2 to 4 carbon atoms include an acetyl group, a propionyl group, and a butyryl group.

[0253] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Examples of the monocyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a pyrrole ring, an imidazole ring, a thiophene ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, and a triazole ring.

[0254] A 1 , A 2 , A3 , A 4 , A 5 and A 6 Examples of the polycyclic aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom, which may have a substituent, include a biphenyl ring, a terphenyl ring, a bipyridine ring, a bithiophene ring, and a bifuran ring.

[0255] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Examples of the fused aromatic ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, a benzofuran ring, a benzimidazole ring, a benzothiophene ring, an indole ring, an indazole ring, a benzoxazole ring, a benzothiazole ring, and a benzotriazole ring.

[0256] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Examples of the optionally substituted aliphatic hydrocarbon ring having an atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom as a ring-constituting atom in the formula (I) include a cyclopentane ring, a cyclohexane ring, a tricyclo[5.2.1.0(2,6)]decane ring, and a decahydronaphthalene ring.

[0257] A 1 , A 2 , A 3 , A 4 , A 5 and A 6 As the ring, a cyclohexane ring is preferred in that the polymer of the present invention exhibits good optical properties.

[0258] In the above chemical formula (P1), a2, a3, a5, and a6 each independently represent an integer of 0 to 2.

[0259] In the above chemical formula (P1), L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR 1 It represents -C(=O)-.

[0260] R 1 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0261] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 Examples of the optionally substituted alkylene group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, an oxymethylene group, an oxyethylene group, an oxytrimethylene group, a methylenedioxy group, or an ethylenedioxy group.

[0262] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 and L 10 In terms of ease of introduction, the alkylene group is preferably a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, or -NR1 -C(=O)- is preferred, and a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, or -C(=O)O- is more preferred.

[0263] In the above chemical formula (P1), Sp 1 and Sp 2 may be the same or different, and each represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR 2 or a halogen atom, and the alkylene group may be substituted with —CH 2 - is independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR 3 It may be substituted with -C(=O)-.

[0264] R 2 , and R 3 may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0265] Sp 1 and Sp 2 In the above formula (1), examples of the alkylene group having 1 to 20 carbon atoms include those having the same structure as that of the above formula (1).

[0266] In the above chemical formula (P1), R 5 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.

[0267] In the above chemical formula (P1), X 1 , X 2 , X 3 , X 4 and X 5 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the above chemical formula (Z1).

[0268] X 1 , X 2 , X 3 , X 4 and X5 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0269] X 1 , X 2 , X 3 , X 4 and X 5 In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0270] X 1 , X 2 , X 3 , X 4 and X 5 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0271] In the above chemical formula (Z1), Ar 2 represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent.

[0272] Ar 2 An example of this is Ar 1 The following structures are also possible:

[0273] In the above chemical formula (Z1), Xz 1 and Xz 2 each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

[0274] Xz 1 and Xz 2 In the above formula, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0275] Xz 1 and Xz 2 In the above formula, examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

[0276] Xz 1 and Xz 2 In the above formula, examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0277] X 1 , X 2 , X 3 , X 4 and X 5 In terms of ease of introduction, a hydrogen atom, a methyl group, or an ethyl group is preferred as the alkyl group.

[0278] In the above chemical formula (P1), X 14 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the above chemical formula (Z2).

[0279] Preferred examples of the structure represented by chemical formula (P1) include compounds in which a central unit represented by any one of the following chemical formulas (1A-1-1) to (1A-6-8) is combined with a side chain unit represented by any one of the following chemical formulas (P1B-2-1) to (P1B-4-8). (The * in the structures of the central unit represented by any one of the (1A-1-1) to (1A-6-8) and the side chain unit represented by any one of the (P1B-2-1) to (P1B-4-8) indicates the bonding position of the central unit and the side chain unit. When there are two * in the structure of the central unit represented by any one of the (1A-1-1) to (1A-6-7), two different ones of the side chain units represented by any one of the (P1B-2-1) to (P1B-4-8) may be combined.)

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] [ka]

[0286] Among the compounds combining the central units represented by the above chemical formulas (1A-1-1) to (1A-6-8) with the side chain units represented by the above chemical formulas (1B-1-1) to (1B-4-8), the combination of the central units (1A-2-1) to (1A-6-6) and the side chain units (P1B-2-1) to (P1B-4-8) is preferred, and the combination of the central units (1A-4-1) to (1A-4-6) and the side chain units (P1B-4-1) to (P1B-4-8) is more preferred.

[0287] The polymer of the present invention may be produced, for example, on a quartz substrate or a cycloolefin polymer substrate by thermal polymerization or photopolymerization, or may be produced by polymerization of the chalcone derivative of the present invention using a reaction apparatus for organic synthesis. [Optical film] The chalcone derivative of the present invention is suitably used for constituting an optical film, preferably a retardation film, more preferably a retardation film having reverse wavelength dispersion.

[0288] The optical film of the present invention is an optical film containing the chalcone derivative of the present invention or the polymer of the present invention, and is particularly preferably an optical film containing the chalcone derivative of the present invention having polymerizability (hereinafter also referred to as the "polymerizable liquid crystal chalcone derivative of the present invention") or the polymer of the present invention.

[0289] In one embodiment of the present invention, an optical film is provided that is composed of a polymer of the chalcone derivative of the present invention in an oriented state. The oriented state means a state in which the molecules are oriented, and the obtained optical film has wavelength dispersion. The optical film of the present invention preferably satisfies the wavelength dispersion Re(450nm) / Re(550nm) of the following formula (α).

[0290] 0.6≦Re(450nm) / Re(550nm)<1.0 (α) [In formula (α), Re(λ) represents a front retardation value for light with a wavelength of λ nm.] The wavelength dispersion Re(450nm) / Re(550nm) of the optical film of the present invention is more preferably 0.63 or more and less than 1.0, and even more preferably 0.65 or more and less than 1.0. When the wavelength dispersion Re(450nm) / Re(550nm) of the optical film of the present invention is equal to or more than the lower limit, it is preferable because circular polarization conversion is possible in the short wavelength region around 450 nm. When the wavelength dispersion Re(450nm) / Re(550nm) of the optical film of the present invention is less than the upper limit, the obtained optical film has reverse wavelength dispersion and can perform uniform polarization conversion in a wide range of wavelengths.

[0291] In a preferred embodiment of the present invention, Ar 1 is a structure having thiophene, and in such a case, an optical film having particularly high reverse wavelength dispersion is easily obtained. In this case, Re(450nm) / Re(550nm) is preferably 0.60 or more and 0.70 or less. When Re(450nm) / Re(550nm) is within the range, when adjusting the wavelength dispersion of the retardation of the optical film to a desired value, the content of the chalcone derivative of the present invention, which is one embodiment of the present invention, can be small, which is advantageous in terms of cost. That is, as described below, the optical film of the present invention may be composed of a structural unit derived from the chalcone derivative of the present invention as well as a structural unit derived from another polymerizable liquid crystal compound (hereinafter also referred to as "polymerizable liquid crystal compound (B)"), and the content of the chalcone derivative of the present invention can be reduced.

[0292] Examples of the polymerizable liquid crystal compound (B) include the following commercially available compounds (LCB-1) to (LCB-4).

[0293] [ka]

[0294] The optical film of the present invention has excellent transparency and can be used in various optical displays. The optical film preferably has a thickness of 0.1 to 10 μm, and more preferably 0.5 to 3 μm in order to reduce photoelasticity.

[0295] When the optical film of the present invention is used as a λ / 4 plate, the retardation value Re(550 nm) of the obtained optical film at a wavelength of 550 nm is preferably 100 to 163 nm, more preferably 130 to 150 nm, and particularly preferably 135 to 150 nm.

[0296] To use the optical film of the present invention as an optical film for a VA (Vertical Alignment) mode, the thickness of the optical film may be adjusted so that Re (550 nm) is preferably about 40 to 100 nm, more preferably about 60 to 80 nm.

[0297] In another embodiment of the present invention, a polarizing plate including the above optical film (hereinafter also referred to as "polarizing plate of the present invention"), particularly an elliptical polarizing plate and a circular polarizing plate, are also provided. The polarizing plate of the present invention can be obtained by combining the optical film of the present invention with a polarizing film. In these elliptical polarizing plates and circular polarizing plates, the optical film of the present invention is bonded to the polarizing film. In another embodiment of the present invention, a broadband circular polarizing plate can also be provided in which the optical film of the present invention is further bonded to the elliptical polarizing plate or the circular polarizing plate as a broadband λ / 4 plate.

[0298] In one embodiment of the present invention, an optical display including the polarizing plate of the present invention (hereinafter also referred to as "optical display of the present invention") can be provided. The optical display of the present invention can be used as, for example, a flat panel display device (FPD) such as a reflective liquid crystal display and an organic electroluminescence (EL) display. The FPD is not particularly limited, and examples thereof include a liquid crystal display device (LCD) and an organic EL display device.

[0299] The optical display of the present invention comprises the polarizing plate of the present invention, and examples thereof include a liquid crystal display device comprising a laminate in which the polarizing plate of the present invention and a liquid crystal panel are laminated together, and an organic EL display device comprising an organic EL panel in which the polarizing plate of the present invention and a light-emitting layer are laminated together. The optical film of the present invention contains the chalcone derivative of the present invention or a polymer derived therefrom, i.e., the optical film of the present invention contains a polymer composed of structural units derived from one or more chalcone derivatives of the present invention.

[0300] The optical film of the present invention may be composed of structural units derived from other polymerizable liquid crystal compounds (hereinafter also referred to as "polymerizable liquid crystal compounds (B)") in addition to structural units derived from the chalcone derivative of the present invention. In this case, the optical film is composed of polymers in an oriented state of these chalcone derivatives and the polymerizable liquid crystal compound (B). By containing structural units derived from the polymerizable liquid crystal compound (B) in addition to structural units derived from the chalcone derivative of the present invention, the optical properties such as wavelength dispersion and retardation value of the optical film, and thermal properties can be adjusted to desired values. Furthermore, when the chalcone derivative of the present invention has high reverse wavelength dispersion (for example, 0.60≦formula (α)≦0.70), it is also advantageous in terms of cost. Further, examples of the polymerizable liquid crystal compound (B) include the commercially available compounds (LCB-1) to (LCB-4) and compounds having a polymerizable group among those described in "Liquid Crystal Handbook (edited by Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd. on October 30, 2000)", Chapter 3, Molecular Structure and Liquid Crystallinity, 3.2 Nonchiral Rod-like Liquid Crystal Molecules, 3.3 Chiral Rod-like Liquid Crystal Molecules". The optical film of the present invention may contain structural units derived from one or more polymerizable liquid crystal compounds (B).

[0301] The optical film of the present invention can be produced, for example, by the following method.

[0302] First, a composition is prepared containing the polymerizable liquid crystal chalcone derivative of the present invention, as necessary, the above polymerizable liquid crystal compound (B), and additives such as a plasticizer, an antioxidant, a polymerization initiator, a polymerization inhibitor, a photosensitizer, an organic solvent, and / or a leveling agent. In particular, it is preferable to contain an organic solvent because it makes film formation easier during film formation, and it is preferable to contain a polymerization initiator because it has the function of curing the obtained optical film.

[0303] When the composition containing the chalcone derivative of the present invention contains an organic solvent, the viscosity is preferably adjusted to, for example, 10 Pa s or less, preferably about 0.1 to 7 Pa s, so as to facilitate application. The viscosity of the mixed solution can be adjusted by the content of the organic solvent.

[0304] When the composition contains an organic solvent, the solid content concentration is, for example, 5 to 50% by mass, preferably 5 to 30% by mass, and more preferably 10 to 30% by mass. The term "solid content" as used herein refers to the components remaining after removing the solvent from the mixed solution (liquid crystal composition). If the solid content concentration is 5% by mass or more, the optical film does not become too thin, and the birefringence required for optical compensation of the liquid crystal panel tends to be imparted. If the solid content concentration is 50% by mass or less, the viscosity of the mixed solution is low, and therefore unevenness in the thickness of the optical film tends to be less likely to occur, which is preferable.

[0305] Examples of the plasticizer include carboxylates, phosphates, and polymer-based plasticizers.

[0306] Specific examples of carboxylates include phthalate esters, trimellitate esters, pyromellitate esters, citrate esters, oleate esters, ricinoleate esters, sebacate esters, stearate esters, adipate esters, and epoxidized esters.

[0307] Examples of the antioxidant include phenol-based antioxidants, amine-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, lactone-based antioxidants, hydroxylamine-based antioxidants, and vitamin E-based antioxidants.

[0308] Examples of the polymerization initiator include a photopolymerization initiator and a thermal polymerization initiator.

[0309] Examples of the photopolymerization initiator include benzoins, benzophenones, benzil ketals, oxime esters, α-hydroxyketones, α-aminoketones, iodonium salts, and sulfonium salts. More specifically, Irgacure 651, Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127, Irgacure 907, Irgacure 369, Irgacure 379, Irgacure 819, Irgacure 754, Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04, and Irgacure 250 (all of which are trade names). , manufactured by Chiba Japan Co., Ltd.), Seikuol BZ, Seikuol Z, Seikuol BEE, Seikuol BIP, Seikuol BBI (all trade names, manufactured by Seiko Chemical Co., Ltd.), Kayacure BP100, Kayacure DETX-S, Kayacure EPA (all trade names, manufactured by Nippon Kayaku Co., Ltd.), Kayacure UVI-6992 (manufactured by Dow), ADEKA ARCLES N-1919T, ADEKA ARCLES NCI-831E, ADEKA ARCLES NCI-930, ADEKA ARCLES NCI-730, ADEKA ARCLES GPA-5001 (all trade names, manufactured by ADEKA Corporation).

[0310] The content of the polymerization initiator is, for example, 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass, and more preferably 0.5 to 10 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal chalcone derivative. If it is within the above range, the chalcone derivative of the present invention can be polymerized without disturbing the orientation of the polymerizable liquid crystal chalcone derivative.

[0311] Examples of the polymerization inhibitor include hydroquinone or hydroquinones having a substituent such as alkyl ether, catechols having a substituent such as alkyl ether, such as butylcatechol, pyrogallols, radical scavengers such as 2,2,6,6-tetramethyl-1-piperidinyloxy radical, thiophenols, β-naphthylamines, and β-naphthols.

[0312] By using a polymerization inhibitor, the polymerization of the polymerizable liquid crystal chalcone derivative can be controlled, and the stability of the obtained optical film can be improved. The content of the polymerization inhibitor is, for example, 0.05 to 30 parts by mass, preferably 0.1 to 10 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal chalcone derivative. If it is within the above range, the polymerizable liquid crystal chalcone derivative can be polymerized without disturbing the alignment of the polymerizable liquid crystal chalcone derivative.

[0313] Examples of the photosensitizer include benzophenones having a substituent such as benzophenone or alkyl ether, xanthones such as xanthone or thioxanthone, anthracene or anthracenes having a substituent such as alkyl ether, phenothiazine, and rubrene.

[0314] By using a photosensitizer, the polymerization of the polymerizable liquid crystal chalcone derivative can be made highly sensitive. The content of the photosensitizer is, for example, 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal chalcone derivative. If it is within the above range, the polymerizable liquid crystal chalcone derivative can be polymerized without disturbing the orientation of the polymerizable liquid crystal chalcone derivative.

[0315] The organic solvent may be any organic solvent capable of dissolving the polymerizable liquid crystal chalcone derivative of the present invention and the polymerizable liquid crystal compound (B) and inert to the polymerization reaction. Examples of the organic solvent include alcohol-based solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, and 1,1,1,3,3,3-hexafluoroisopropanol; ester-based solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, gamma-butyrolactone, propylene glycol methyl ether acetate, and ethyl lactate; acetone, methyl ethyl ketone, and cyclopentanone. , ketone-based solvents such as cyclohexanone, methyl amyl ketone, or methyl isobutyl ketone; non-chlorine-based aliphatic hydrocarbon solvents such as pentane, hexane, or heptane; non-chlorine-based aromatic hydrocarbon solvents such as toluene, xylene, or phenol, nitrile-based solvents such as acetonitrile; ether-based solvents such as tetrahydrofuran, dimethoxyethane, or 1,3-dioxolane; and chlorine-based solvents such as chloroform or chlorobenzene; amide-based solvents such as N-methylpyrrolidone (NMP) or N,N-dimethylformamide (DMF). From the viewpoint of easily dissolving the polymerizable liquid crystal chalcone derivative, ester-based solvents, ketone-based solvents, non-chlorine-based aromatic hydrocarbon solvents, ether-based solvents, and amide-based solvents are preferred, and ketone-based solvents, ether-based solvents, and amide-based solvents are more preferred. These organic solvents may be used alone or in combination.

[0316] The content of the organic solvent is preferably 100 to 10,000 parts by mass, more preferably 200 to 5,000 parts by mass, and even more preferably 500 to 2,500 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal chalcone derivative. If the content of the organic solvent is equal to or greater than the lower limit, the optical film does not become too thin, and the birefringence required for optical compensation of the liquid crystal panel tends to be imparted. If the content of the organic solvent is equal to or less than the upper limit, the viscosity of the mixed solution is low, and therefore unevenness in the thickness of the optical film tends to be less likely to occur.

[0317] Examples of the leveling agent include radiation curable paint additives BYK-352, BYK-353, BYK-361N (all of which are trade names, manufactured by BYK-Chemie Japan K.K.), paint additives SH28PA, DC11PA, ST80PA (all of which are trade names, manufactured by Dow Corning Toray Co., Ltd.), paint additives KP321, KP323, X22-161A, KF6001 (all of which are trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), and fluorine-based additives F-445, F-470, F-479 (all of which are trade names, manufactured by Dainippon Ink and Chemicals, Inc.).

[0318] By using the leveling agent, the obtained optical film can be made smooth. Furthermore, in the manufacturing process of the optical film, the fluidity of the composition can be controlled, and the crosslinking density of the optical film obtained by polymerizing the polymerizable liquid crystal chalcone derivative can be adjusted. The specific value of the content of the leveling agent is, for example, 0.05 to 30 parts by mass, preferably 0.05 to 10 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal chalcone derivative. Within the above range, the polymerizable liquid crystal chalcone derivative can be polymerized without disturbing the alignment of the polymerizable liquid crystal chalcone derivative.

[0319] The composition thus obtained is applied to a support substrate or the like. The coating amount and concentration of the composition can be appropriately adjusted to adjust the film thickness so as to provide a desired phase difference. In the case of a composition containing a constant amount of the chalcone derivative and the polymerizable liquid crystal compound (B) of the present invention, the phase difference value (retardation value, Re(λ)) of the obtained optical film is determined by the following formula, so the film thickness d may be adjusted to obtain a desired Re(λ).

[0320] Re(λ)=d×Δn(λ) (In the formula, Re(λ) represents a retardation value at a wavelength of λ nm, d represents a film thickness, and Δn(λ) represents a birefringence at a wavelength of λ nm.) Examples of the method for applying the composition to the supporting substrate include extrusion coating, direct gravure coating, reverse gravure coating, CAP coating, and die coating. Examples of the method for applying the composition to the supporting substrate include a method using a coater such as a dip coater, a bar coater, or a spin coater.

[0321] Examples of the supporting substrate include glass, plastic sheets, plastic films, and light-transmitting films. Examples of the light-transmitting films include polyolefin films such as polyethylene, polypropylene, and norbornene-based polymers, polyvinyl alcohol films, polyethylene terephthalate films, polymethacrylic acid ester films, polyacrylic acid ester films, cellulose ester films, polyethylene naphthalate films, polycarbonate films, polysulfone films, polyethersulfone films, polyetherketone films, polyphenylene sulfide films, and polyphenylene oxide films.

[0322] For example, even in processes requiring strength of the optical film, such as a lamination process, a transportation process, and a storage process, the use of a supporting substrate allows the optical film of the present invention to be easily handled without breaking.

[0323] Also, it is preferable to form an alignment film on a supporting substrate, and then coat the composition containing the polymerizable liquid crystal chalcone derivative on the alignment film. The alignment film preferably has solvent resistance that does not dissolve in the mixed solution when coating the composition containing the polymerizable liquid crystal chalcone derivative, has heat resistance when removing the solvent or when heat treating the liquid crystal alignment, and does not peel off due to friction during rubbing, and is preferably made of a polymer or a composition containing a polymer.

[0324] Examples of the polymer include polyamides and gelatins having an amide bond in the molecule, polyimides having an imide bond in the molecule, and their hydrolyzates such as polyamic acid, polyvinyl alcohol, alkyl-modified polyvinyl alcohol, polyacrylamide, polyoxazole, polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid, polyacrylic acid esters, and polymethacrylic acid esters. These polymers may be used alone, or two or more of them may be mixed or copolymerized. These polymers can be easily obtained by polycondensation through dehydration or deamination, chain polymerization such as radical polymerization, anionic polymerization, or cationic polymerization, coordination polymerization, ring-opening polymerization, or the like.

[0325] These polymers can be dissolved in a solvent and applied.The solvent is not particularly limited, but specifically includes water; alcohols such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, or 1,1,1,3,3,3-hexafluoroisopropanol; ester-based solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, gamma-butyrolactone, propylene glycol methyl ether acetate, or ethyl lactate; ketone-based solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, or methyl isobutyl ketone; non-chlorine-based aliphatic hydrocarbon solvents such as pentane, hexane, or heptane; non-chlorine-based aromatic hydrocarbon solvents such as toluene or xylene, and nitrile-based solvents such as acetonitrile; ether-based solvents such as tetrahydrofuran, dimethoxyethane, or 1,3-dioxolane; chlorine-based solvents such as chloroform or chlorobenzene; and the like. These organic solvents may be used alone or in combination.

[0326] In addition, commercially available alignment film materials may be used as they are to form the alignment film. Examples of commercially available alignment film materials include Sunever (registered trademark, manufactured by Nissan Chemical Industries, Ltd.) and Optomer (registered trademark, manufactured by JSR Corporation).

[0327] By using such an alignment film, it is not necessary to control the refractive index by stretching, and therefore the in-plane variation in birefringence is reduced, which has the effect of providing a large optical film on the supporting substrate that can accommodate larger flat panel displays (FPDs).

[0328] As a method for forming an alignment film on the supporting substrate, for example, a commercially available alignment film material or a chalcone derivative serving as an alignment film material is applied in a solution onto the supporting substrate, and then annealed, thereby forming an alignment film on the supporting substrate.

[0329] The thickness of the alignment film thus obtained is, for example, 10 nm to 10,000 nm, and preferably 10 nm to 1,000 nm. Within the above range, the polymerizable liquid crystal chalcone derivative or the like can be aligned at a desired angle on the alignment film.

[0330] These alignment films can be subjected to rubbing or irradiation with polarized UV light as necessary. By forming the alignment film, the polymerizable liquid crystal chalcone derivatives and the like can be aligned in a desired direction.

[0331] As a method for rubbing the alignment film, for example, a method can be used in which a rotating rubbing roll wrapped with a rubbing cloth is brought into contact with the alignment film that is placed on a stage and being transported.

[0332] As described above, in the process of preparing the optical film, the polymerizable liquid crystal film may be laminated on the alignment film laminated on any supporting substrate. In this case, the production cost can be reduced compared to the method of preparing a liquid crystal cell and injecting the mixed solution into the liquid crystal cell. Furthermore, the film can be produced in the form of a roll film.

[0333] The solvent may be dried while the polymerization is proceeding, but it is preferable from the viewpoint of film formability to dry most of the solvent before the polymerization.

[0334] Examples of methods for drying the solvent include natural drying, ventilation drying, and reduced pressure drying. A specific heating temperature is preferably 10 to 120° C., and more preferably 50 to 120° C. A heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. If the heating temperature and heating time are within the above ranges, a supporting substrate that does not necessarily have sufficient heat resistance can be used as the supporting substrate.

[0335] Next, the polymerizable liquid crystal film obtained above is polymerized and cured. This results in a film in which the orientation of the polymerizable liquid crystal chalcone derivative is fixed, that is, a film containing a polymer of the polymerizable liquid crystal chalcone derivative, which is one embodiment of the present invention (hereinafter, also referred to as a "polymerized film"). This allows the production of a polymerized film with a small change in refractive index in the planar direction of the film and a large change in refractive index in the normal direction of the film.

[0336] The method of polymerizing the polymerizable liquid crystal film is determined according to the type of the polymerizable liquid crystal chalcone derivative. If the polymerizable group contained in the polymerizable liquid crystal chalcone derivative is photopolymerizable, the polymerizable liquid crystal film can be polymerized by photopolymerization, and if the polymerizable group is thermally polymerizable, the polymerizable liquid crystal film can be polymerized by thermal polymerization. In the present invention, it is particularly preferable to polymerize the polymerizable liquid crystal film by photopolymerization. Since the polymerizable liquid crystal film can be polymerized at a low temperature by photopolymerization, the range of heat resistance of the support substrate can be expanded. In addition, it is easy to manufacture industrially. In addition, photopolymerization is preferable from the viewpoint of film formation. Photopolymerization is performed by irradiating the polymerizable liquid crystal film with visible light, ultraviolet light, or laser light. From the viewpoint of handling, the light irradiation, which is particularly preferably ultraviolet light, may be performed while heating to a temperature at which the polymerizable liquid crystal chalcone derivative takes on a liquid crystal phase. At this time, the polymerized film can be patterned by masking or the like to obtain a patterned optical film.

[0337] Furthermore, the optical film of the present invention is thinner than a stretched film in which retardation is imparted by stretching a polymer.

[0338] The method for producing an optical film of the present invention may further include a step of peeling off the supporting substrate. By adopting such a configuration, the obtained laminate is a film consisting of an alignment film and an optical film. In addition to the step of peeling off the supporting substrate, the method may further include a step of peeling off the alignment film. By adopting such a configuration, an optical film can be obtained. EXAMPLES

[0339] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0340] <Film thickness measurement> The thickness of the films in the examples was measured using a spectroscopic ellipsometer (manufactured by JA Woollam, product name: RC2-U).

[0341] <Heat treatment> The heat treatment of the films in the examples was carried out using an inert oven (manufactured by ESPEC, product name: IPHH-202) that is a thermostatically controlled, non-oxidizing atmosphere.

[0342] <Measurement of phase difference characteristics (Re)> The retardation characteristics (Re) in the examples were measured using a sample tilt type automatic birefringence meter (manufactured by AXOMETRICS, product name: AxoScan) with light having a wavelength of 589 nm.

[0343] Re = (ny - nx) × d (III) (In formula (III), nx represents the refractive index in the fast axis direction (the direction with the smallest refractive index) in the film plane, ny represents the refractive index in the slow axis direction (the direction with the largest refractive index) in the film plane, and d (nm) represents the thickness of the film.) [Synthesis Example 1]

[0344] [ka]

[0345] 2,5-Dihydroxybenzaldehyde (58.1g, 421mmol) and 2-acetyl-5-chlorothiophene (67.5g, 421mmol) were dissolved in methanol (216mL), and then 48% aqueous sodium hydroxide solution (126mL, 2.25mol) was added dropwise under ice cooling. The reaction system was stirred at 50°C for 3 hours, and then acetic acid (168mL, 2.93mol) was added under ice cooling. Water (270mL), toluene (95mL), and isopropyl alcohol (13.5mL) were added to the resulting reaction mixture, and then water (54mL) was added. The resulting solid was filtered and washed with water (50mL) and toluene (270mL). The resulting solid was suspended in a mixed solvent of acetonitrile (235mL) and methanol (59mL), and the system was heated in an oil bath at 70°C, and stirring was continued for 1.5 hours. The system was cooled again in an ice bath, and the solid generated in the system was filtered off using a Buchner funnel. The solid was then washed by pouring acetonitrile (270 mL) from the top of the Buchner funnel, and then vacuum dried to obtain 81.4 g (yield: 69%) of compound (2-2-2) as yellow microcrystals. 1 H-NMR (400MHz, DMSO-d 6 )δ9.88-8.62(br,2H),8.12(d,J=4.1Hz,1H),7.95(d,J=15.8Hz,1H),7.60 (d,J=15.8Hz,1H),7.31(d,J=4.1Hz,1H),7.19(s,1H),6.75-6.68(m,2H). [Example 1]

[0346] [ka]

[0347] Under an argon atmosphere, a solution of compound (2-2-2) (0.281 g, 1.00 mmol) and 4-dimethylaminopyridine (catalytic amount) in tetrahydrofuran (5 mL) was ice-cooled, and a solution of 4-[[4-[2-[[4-[2-(acryloyloxy)ethoxy]-4-oxobutanoyl]oxy]ethyl]phenoxy]carbonyl]cyclohexane-1-carboxylic acid (2.45 g, 5.00 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.22 mL, 6.90 mmol) in tetrahydrofuran (2.5 mL) was added, and the temperature was raised to room temperature and stirred for 4.5 hours. The solvent was distilled off under reduced pressure, water (50 mL) was added to the residue, and extraction was performed with ethyl acetate (2 x 50 mL). The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography, and then methanol (50 mL) was added to the resulting yellow liquid and stirred for 1.5 hours. The precipitated solid was filtered off and dissolved in acetone (30 mL), and activated carbon (90 mg) was added and stirred for 2 hours. Insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Hexane was added to the residue, and the precipitated solid was filtered off to obtain compound 1 (yield: 0.490 g, yield: 40%) as a white solid. 1 H-NMR (400MHz, CDCl 3 ):δ7.84(d,J=15.7Hz,1H),7.65(d,J=4.1Hz,1H),7.48(d,J=2.4Hz,1H),7.30-7 .20(m,5H),7.20-7.12(m,2H),7.06-6.98(m,5H),6.44(dd,J=17.3,1.4Hz,2H),6 .14(dd,J=17.3,10.4Hz,2H),5.87(dd,J=10.4,1.4Hz,2H),4.40-4.25(m,12H),2 .94(t,J=6.99Hz,4H),2.75-2.56(m,12H),2.41-2.25(m,8H),1.80-1.63(m,8H). [Example 1-1] A mixture of polyvinyl alcohol (3.0 parts by weight) and water (97 parts by weight) was cast onto a quartz glass substrate, spin-coated at 3000 rpm for 60 seconds, and dried in an oven at 100°C for 10 minutes to obtain a thin film (film thickness 0.1 μm). The thin film was rubbed in one direction with a rubbing roll wrapped with a rubbing cloth at a uniform pressure to obtain a quartz glass with a liquid crystal alignment film.

[0348] A mixture of compound 1 (15 parts by weight) and chloroform (85 parts by weight) was cast onto a quartz glass substrate with a liquid crystal alignment film, spin-coated at 1500 rpm for 60 seconds, and then dried and aligned in an oven at 115°C for 5 minutes to obtain a high retardation film (film thickness 2.3 μm) with a retardation amount Re of 114 nm. [Example 2]

[0349] [ka]

[0350] Under an argon atmosphere, a solution of compound (2-2-2) (1.97 g, 7.00 mmol) and 4-dimethylaminopyridine (catalytic amount) in tetrahydrofuran (35 mL) was ice-cooled, and a solution of 4-[[4-[2-[[4-[2-(methacryloyloxy)ethoxy]-4-oxobutanoyl]oxy]ethyl]phenoxy]carbonyl]cyclohexane-1-carboxylic acid (20.1 g, 39.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (9.76 mL, 55.3 mmol) in tetrahydrofuran (17.5 mL) was added, and the mixture was warmed to room temperature and stirred for 6 hours. The solvent was distilled off under reduced pressure, and water (175 mL) was added to the residue, followed by extraction with ethyl acetate (2 x 175 mL). The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Methanol (500 mL) was added to the residue, and the precipitated solid was filtered off and purified by silica gel column chromatography. The resulting yellow liquid was dissolved in acetone (80 mL), activated carbon (600 mg) was added, and the mixture was stirred for 4 hours. Insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Hexane was added to the residue, and the precipitated solid was filtered off to obtain compound 2 as a white solid (yield: 2.34 g, yield: 27%). 1 H-NMR (400MHz, CDCl 3 ):δ7.85(d,J=15.7Hz,1H),7.66(d,J=4.1Hz,1H),7.48(d,J=2.3Hz,1H),7.32-7.21(m,5H),7.20-7.13(m,2H),7.08-6.98(m,5H),6.13 (s,2H),5.60(s,2H),4.42-4.22(m,12H),2.94(t,J=7.0Hz,4H),2.75-2.54(m,12H),2.42-2.23(m,8H),1.95(s,6H),1.80-1.63(m,8H). [Example 3]

[0351] [ka]

[0352] Under an argon atmosphere, a solution of compound (2-2-2) (2.25 g, 8.00 mmol), 4-dimethylaminopyridine (catalytic amount) and 2,6-di-tert-butyl-4-methylphenol (0.20 g) in tetrahydrofuran (40 mL) was cooled on ice, and a solution of 4'-[[4-(acryloyloxy)butoxy]carbonyl]-[1,1'-bi(cyclohexane)]-4-carboxylic acid (17.3 g, 45.6 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (11.1 mL, 63.2 mmol) in tetrahydrofuran (20 mL) was added, and the mixture was warmed to room temperature and stirred for 7.5 hours. The solvent was distilled off under reduced pressure, and water (200 mL) was added to the residue, followed by extraction with ethyl acetate (2 x 200 mL). The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Methanol was added to the residue, and the precipitated solid was filtered off and purified by silica gel column chromatography. The obtained yellow-white solid was dissolved in acetone (80 mL), activated carbon (522 mg) was added, and the mixture was stirred for 30 minutes. Insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Hexane was added to the residue, and the precipitated solid was filtered off to obtain compound 3 as a white solid (yield: 2.86 g, yield: 35%). 1 H-NMR (400MHz, CDCl 3 ):δ7.83(d,J=15.6Hz,1H),7.64(d,J=4.1Hz,1H),7.45(d,J=1.9Hz,1H),7.33-7.20(m,1H),7.18-7. 08(m,2H),7.05-6.97(m,1H),6.41(dd,J=17.3,1.4Hz,2H),6.13(dd,J=17.3,10.4Hz,2H),5.84(dd, J=10.4,1.4Hz,2H),4.19(t,J=5.9Hz,4H),4.11(t,J=5.7Hz,4H),2.62-2.43(m,2H),2.29-2.13(m,6 H),2.07-1.96(m,4H),1.94-1.68(m,16H),1.65-1.49(m,4H),1.48-1.34(m,4H),1.22-0.96(m,12H). [Example 4]

[0353] [ka]

[0354] Under an argon atmosphere, a solution of compound (2-2-2) (1.68 g, 6.00 mmol), 4-dimethylaminopyridine (catalytic amount) and 2,6-di-tert-butyl-4-methylphenol (150 mg) in tetrahydrofuran (30 mL) was ice-cooled, and a solution of 4-[[4-(acryloyloxy)butoxy]carbonyl]cyclohexane-1-carboxylic acid (7.52 g, 25.2 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (6.14 mL, 34.8 mmol) in tetrahydrofuran (15 mL) was added, and the temperature was raised to room temperature and stirred for 6 hours. The solvent was distilled off under reduced pressure, water (150 mL) was added to the residue, and extraction was performed with ethyl acetate (2 x 150 mL). The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and ethyl acetate was added to the obtained yellow liquid, which was then added dropwise to hexane. The resulting precipitate was filtered off, dissolved in acetone (80 mL), activated carbon (382 mg) was added, and the mixture was stirred for 1.5 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was dropped into hexane. The precipitated solid was filtered off to obtain compound 4 as a white solid (yield: 2.31 g, yield: 46%). 1 H-NMR (400MHz, DMSO-d 6 ):δ8.30(d,J=4.3Hz,1H),7.95(d,J=2.2Hz,1H),7.91(d,J=15.8Hz,1H),7.61(d,J=15.6Hz,1H),7.42(d,J= 4.0Hz,1H),7.35-7.25(m,2H),6.34(ddd,J=17.3,1.6,1.0Hz,2H),6.19(ddd,J=17.3,10.2,1.2Hz,2H),5.9 6(ddd,J=10.3,1.6,0.9Hz,2H),4.15(t,J=5.9Hz,4H),4.08(t,J=5.5Hz,4H),2.73(tt,J=11.6,3.6Hz,1H), 2.64(tt,J=11.5,3.6Hz,1H),2.44-2.32(m,2H),2.22-2.11(m,4H),2.07-1.97(m,4H),1.76-1.41(m,16H). [Industrial Applicability]

[0355] The chalcone derivative of the present invention can be used to form an optical film, particularly a retardation film. Therefore, the present invention has high industrial applicability.

Claims

1. A chalcone derivative represented by the following chemical formula (1). 【Chemistry 1】 [In the above chemical formula (1), Ar １ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A １ , A ２ , A ３ , A ４ , A ５ and A ６ each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L １ , L ２ , L ３ , L ４ , L ５ , L ６ , L ７ , L ８ , L ９ and L １０ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, —O—, —C(═O)O—, —C(═O)—, or —NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ and Sp ２ may be the same or different and represent a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. R ２ , and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. F.G. １ and Fg ２ may be the same or different and represent a hydrogen atom or a polymerizable group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). 【Chemistry 2】 [In the above chemical formula (Z1), Ar ２ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz １ and Xz ２ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

2. The chalcone derivative according to claim 1, represented by the following chemical formula (1'): 【Chemistry 3】 [In the above chemical formula (1'), Ar １ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A １ , A ２ , and A ３ each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L １ , L ２ , L ３ , L ４ , and L ５ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, —O—, —C(═O)O—, —C(═O)—, or —NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ represents an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. R ２ , and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. F.G. １ represents a hydrogen atom or a polymerizable group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). 【Chemistry 4】 [In the above chemical formula (Z1), Ar ２ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz １ and Xz ２ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

3. Ar １ is a ring selected from the group consisting of monocyclic aromatic rings and polycyclic aromatic rings, the ring constituent atoms of which are selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms (these monocyclic aromatic rings and polycyclic aromatic rings may have a substituent).

4. Ar １ The following chemical formula (Ar １ −1) to (Ar １ 3. The chalcone derivative according to claim 1 or 2, which has a structure represented by the following formula: 【Chemistry 5】 [The above-mentioned chemical formula (Ar １ -1) to (Ar １ -7) Medium, X ６ , X ７ , X ８ , X ９ , X １０ , X １１ , X １２ , and X １３ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkylthio group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms. R ４ represents an alkyl group having 1 to 10 carbon atoms. ** represents Ar in the above chemical formula (1). １ represents the bonding position to other moieties excluding

5. The chalcone derivative according to claim 1 or 2, represented by the following chemical formula (1-2): 【Chemistry 6】 [In the above chemical formula (1-2), A １ , A ２ and A ３ each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L ２ , L ３ , L ４ and L ５ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, —O—, —C(═O)O—, —C(═O)—, or —NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. R ２ and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. F.G. １ represents a hydrogen atom or a polymerizable group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

6. A １ and A ４ The chalcone derivative according to claim 1 or 2, wherein is a cyclohexane ring.

7. A method for producing a chalcone derivative represented by the following chemical formula (1'), comprising a step of condensing a dihydroxy compound represented by the following chemical formula (2) with a compound represented by the following chemical formula (3). 【Chemistry 7】 [In the above chemical formula (2), Ar １ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. F.G. ３ represents a hydroxy group, a carboxy group, or an amino group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). 【Chemistry 8】 [In the above chemical formula (Z1), Ar ２ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz １ and Xz ２ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. 【Chemistry 9】 [In the above chemical formula (3), A １ , A ２ , and A ３ each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L ２ , L ３ , L ４ and L ５ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. F.G. １ represents a hydrogen atom or a polymerizable group. R ２ , and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. F.G. ４ represents a hydroxy group, a carboxy group, or a chlorocarbonyl group. 【Chemistry 10】 [In the above chemical formula (1'), Ar １ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A １ , A ２ , and A ３ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2 and a3 each independently represent an integer of 0 to 2. L １ , L ２ , L ３ , L ４ , and L ５ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ represents a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is represented by -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. R ２ , and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. F.G. １ represents a hydrogen atom or a polymerizable group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). 【Chemistry 11】 [In the above chemical formula (Z1), Ar ２ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz １ and Xz ２ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.

8. Fg of the dihydroxy compound represented by the above chemical formula (2) ３ is a hydroxy group, and Fg of the compound represented by the above chemical formula (3) ４ is a carboxy group or a chlorocarbonyl group, and L of the chalcone derivative represented by the above chemical formula (1') １ The method for producing a chalcone derivative according to claim 7, wherein is -C(=O)O-.

9. A polymer comprising a structure represented by the following chemical formula (P1) as a repeating unit. 【Chemistry 12】 [In the above chemical formula (P1), Ar １ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. A １ , A ２ , A ３ , A ４ , A ５ and A ６ each independently represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. a2, a3, a5, and a6 each independently represent an integer of 0 to 2. L １ , L ２ , L ３ , L ４ , L ５ , L ６ , L ７ , L ８ , L ９ and L １０ each independently represents a single bond, an optionally substituted alkylene group having 1 to 4 carbon atoms, -O-, -C(=O)O-, -C(=O)-, or -NR １ It represents —C(═O)—. R １ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. Sp １ and Sp ２ may be the same or different and represent a single bond or an alkylene group having 1 to 20 carbon atoms, and a hydrogen atom contained in the alkylene group is -OR ２ or a halogen atom, and the alkylene group contains —CH ２ - is each independently -O-, -S-, -C(=O)O-, -C(=O)-, or -NR ３ It may be substituted with -C(=O)-. R ２ , and R ３ may be the same or different and represent a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms. R ５ represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. X １ , X ２ , X ３ , X ４ and X ５ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z1). X １４ represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a group represented by the following chemical formula (Z2). 【Chemistry 13】 [In the above chemical formula (Z1), Ar ２ represents a ring selected from the group consisting of a monocyclic aromatic ring, a polycyclic aromatic ring, a condensed aromatic ring, and an aliphatic hydrocarbon ring, the ring of which is composed of an atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, and these monocyclic aromatic rings, polycyclic aromatic rings, condensed aromatic rings, and aliphatic hydrocarbon rings may have a substituent. Xz １ and Xz ２ each independently represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms. 【Chemistry 14】 [In the above chemical formula (Z2), R ６ represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.

10. A composition comprising the chalcone derivative according to claim 1.

11. An optical film comprising the chalcone derivative according to claim 1.

12. An optical film comprising the polymer of claim 9.

13. 13. The optical film according to claim 11, wherein a retardation (Re) measured using a 589 nm light source and represented by the following formula (A) is 1 nm or more. Re=(ny-nx)×d (A) [In formula (A), nx represents the refractive index in the fast axis direction in the film plane, ny represents the refractive index in the slow axis direction in the film plane, and d represents the film thickness.]

14. The optical film according to claim 13 , wherein the retardation (Re) satisfies the following formula (I): Re(450)≦Re(550)...(I) (In formula (I), Re(450) represents an in-plane retardation value measured at a wavelength of 450 nm, and Re(550) represents an in-plane retardation value measured at a wavelength of 550 nm.)

15. A polarizing plate comprising the optical film according to claim 11 or 12.

16. An optical display comprising the polarizer of claim 15.

17. A method for producing an optical film, comprising the step of applying the composition according to claim 10.

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