Compound having a binaphthalene skeleton

Abstract

To provide a novel compound that is a raw material excellent in a color phase and various properties of a resin (e.g. optical properties, heat resistance, moldability).SOLUTION: A compound having a binaphthalene skeleton represented by formula (1) (where R1 and R2 independently represent a hydrogen atom, a halogen atom, a hydrocarbon group which may have a C1-12 aromatic group, Ar1 and Ar2 are an optionally substituted, C6-10 aromatic group, L1 and L2 are a C1-12 alkylene group, j and k independently represent an integer of 0 to 5, m1, m2, n1, n2 independently represent an integer of 0 to 4, m1+m2≥1, where, m1+n1 is an integer of 4 or less, m2+n2 is an integer of 2 or less). The content of a palladium element in the compound is 0 to 50 ppm.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound having a binaphthalene skeleton, which is suitable as a monomer for forming a thermoplastic resin constituting an optical member typified by an optical lens or an optical film.

Background Art

[0002] In recent years, thermoplastic resin materials such as polycarbonate and polyester using an alcohol having a binaphthalene skeleton typified by 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BN2EO) as a raw material have attracted attention as optical members such as optical lenses and optical sheets because of their excellent optical properties, heat resistance, moldability, etc. For example, Patent Document 1 discloses a polyester resin using an alcohol having BN2EO as a raw material. Although the refractive index of the polyester resin using the alcohol is described as 1.67, further improvement of the above characteristics has been required with the recent rapid technological innovation. Therefore, aiming at further increasing the refractive index, a polycarbonate resin obtained by copolymerizing 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene (BNEF) with BN2EO has been developed in Patent Document 2. However, the resin described in the patent document still has room for improvement in refractive index.

[0003] By the way, as a method for producing 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, a method of reacting 1,1'-bi-2-naphthol with ethylene carbonate described in Patent Document 3 and a method of reacting 1,1'-bi-2-naphthol with ethylene carbonate or ethylene oxide described in Patent Document 4 have been disclosed. Although products with high purity and little coloring can be obtained, the optical properties of the thermoplastic resin material using the alcohol as a raw material are still not satisfactory and there is room for improvement.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

[0005] In the present invention, the compound of the following formula (1) designed by molecular design has a specific metal content such as a low palladium content, and provides a novel compound having a binaphthalene skeleton excellent in the hue and various properties (optical properties, heat resistance, moldability, etc.) of its raw materials and the resin using the raw materials. [Means for Solving the Problems]

[0006] The present invention has been achieved as a result of studies to solve the problems of the above prior art, and provides a compound having a binaphthalene skeleton that has a certain quality and is excellent as a polymer raw material. Specifically, the present invention relates to a compound having a binaphthalene skeleton shown below.

[0007] [1] A compound having a binaphthalene skeleton represented by the following formula (1), [Chemical Formula] (In the formula, R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a hydrocarbon group which may contain an aromatic group having 1 to 12 carbon atoms, Ar 1 and Ar 2 are aromatic groups which may have a substituent having 6 to 10 carbon atoms, L 1 and L 2is an alkylene group having 1 to 12 carbon atoms, j and k are each independently an integer of 0 to 5, m1, m2, n1, and n2 are each independently an integer of 0 to 4, and m1 + m2 ≥ 1. However, m1 + n1 is an integer of 4 or less, and m2 + n2 is an integer of 2 or less.) A compound having a binaphthalene skeleton, wherein the content of palladium element in the compound having a binaphthalene skeleton satisfies the following formula (2). 0 ≦ Pd ≦ 50 ppm (2)

[0008] [2] The compound having a binaphthalene skeleton according to item 1 above, wherein the formula (1) is at least one of the following formulas (1a) to (1f). [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] (In the formula, R 3 ~R 14 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group which may contain an aromatic group having 1 to 12 carbon atoms. Ar 1 and Ar 2 , L 1 and L 2 , j and k are the same as in the formula (1).)

[0009] [3] The compound having a binaphthalene skeleton according to item 2 above, wherein the formula (1) is the formula (1d). [4] Ar 1 or Ar 2The compound having a binaphthalene skeleton according to any one of the preceding items 1 to 3, wherein the group is a phenyl group or a naphthyl group. [5] A method for using the compound having a binaphthalene skeleton according to item 1 above as a raw material for a thermoplastic resin. [Advantages of the Invention]

[0010] The binaphthalene compound produced by the present invention has a high refractive index, and by optimizing the amount of the palladium-based catalyst used during synthesis, the content of specific metals such as palladium content is reduced, so it can be easily removed by activated carbon treatment or a metal removal treatment similar thereto. Therefore, a compound having a binaphthalene skeleton with a very low metal content can be produced efficiently. Furthermore, since the binaphthalene compound has two highly reactive hydroxy groups, it can also be suitably used as a monomer component of thermoplastic resins (for example, polyester resins, polycarbonate resins, polyester carbonate resins, polyurethane resins, etc.). [Brief Description of the Drawings]

[0011]

Figure 1

[0012] The present invention will be described in detail, but the description of the constituent elements described below is a representative example of the embodiments of the present invention and is not limited to these contents.

[0013] [Compound Having a Binaphthalene Skeleton] The compound of the present invention is a compound having a binaphthalene skeleton represented by the following formula (1), that is, a hydrocarbon having at least one hydroxy group at any one of the 2 to 8 positions and 2' to 8' positions of the naphthalene ring of the binaphthalene moiety in which the 1,1'-positions of naphthalene are directly bonded is substituted or added, and further, an aromatic group having a substituent having 6 to 10 carbon atoms may be substituted or added.

[0014] [Chemical formula] (In the formula, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group which may contain an aromatic group having 1 to 12 carbon atoms, Ar 1 and Ar 2 each represent an aromatic group which may have a substituent having 6 to 10 carbon atoms, L 1 and L 2 each represent an alkylene group having 1 to 12 carbon atoms, j and k each independently represent an integer of 0 to 5, m1, m2, n1, and n2 each independently represent an integer of 0 to 4, and m1 + m2 ≥ 1. However, m1 + n1 is an integer of 4 or less, and m2 + n2 is an integer of 2 or less.)

[0015] In the above formula (1), R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group which may contain an aromatic group having 1 to 12 carbon atoms, and a hydrogen atom, a methyl group, or a phenyl group is preferred.)

[0016] In the above formula (1), examples of the hydrocarbon group represented by R 1 and R 2 include an alkyl group, a cycloalkyl group, an aryl group, a naphthyl group, an aralkyl group, etc. Specific examples of the alkyl group include C 1-6 alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, C 1-4 alkyl groups, C 1-3 alkyl groups are preferred, C 1-3 alkyl groups are more preferred, and among them, a methyl group or an ethyl group is even more preferred.)

[0017] Also, specific examples of the cycloalkyl group include C 5-8 cycloalkyl groups such as cyclopentyl group, cyclohexyl group, C 5-6 cycloalkyl groups are preferred, and C 5-6 cycloalkyl groups are more preferred.)

[0018] Further, specific examples of the aryl group include a phenyl group, an alkylphenyl group (such as a mono- or dimethylphenyl group, a tolyl group, a 2-methylphenyl group, a xylyl group, etc.), and a phenyl group is more preferable.

[0019] Further, specific examples of the aralkyl group include a benzyl group, a phenethyl group, etc., and an aryl-C 6-10 aryl-C 1-4 alkyl group and the like can be preferably exemplified. Further, as the halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. are preferable.

[0020] In the above formula (1), R 1 and R 2 The substitution numbers n1 and n2 of the substituents may be such that n1 is 0 to 4 (for example, 1 to 3), preferably 0 to 2, more preferably 0 to 1. Further, n2 may be 0 to 3 (for example, 1 to 3), preferably 0 to 2, more preferably 0 to 1. Note that n1 and n2 may be the same or different numbers in each naphthalene ring, and may also be the same or different numbers in different naphthalene rings. Further, the substituents R 1 and R 2 are the same as above, and may be the same or different substituents in the same naphthalene ring and different naphthalene rings, respectively.

[0021] In the above formula (1), L 1 and L 2 each independently represents a divalent linking group, which is an alkylene group having 1 to 12 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably an ethylene group. Usually, L 1 and L 2 may be the same alkylene group in the binaphthalene ring. Further, L 1 and L 2 may be the same or different from each other in different naphthalene rings, and usually may be the same.

[0022] The oxyalkylene group (OL 1 ) and the number (number of moles added) j and k of (OL 2 ) can each be selected from the range of 0 to 5. The lower limit is preferably 0 or more, and the upper limit is preferably 4 or less, more preferably 3 or less, and even more preferably 2 or less. Particularly preferably, it is 0 or 1, and most preferably 1. Note that j and k may be integers or average values, and may be the same or different in different naphthalene rings.

[0023] In the above formula (1), Ar 1 and Ar 2 each independently represent an aromatic group having 6 to 10 carbon atoms, and a phenyl group or a naphthyl group is preferred. The groups Ar 1 and Ar 2 may be different from each other or the same, but are usually the same. Also, the bonding positions of Ar 1 and Ar 2 are preferably the 3- and 3'-positions, 4- and 4'-positions, 5- and 5'-positions, 6- and 6'-positions, 7- and 7'-positions, or 8- and 8'-positions of the binaphthalene ring, more preferably the 4- and 4'-positions, 6- and 6'-positions, or 7- and 7'-positions, and even more preferably the 6- and 6'-positions.

[0024] In the above formula (1), the substitution numbers m1 and m2 of Ar 1 and Ar 2 only need to satisfy m1 + m2 ≧ 1. For example, m1 may be from 0 to 4, preferably from 0 to 2, and even more preferably from 0 to 1. Also, m2 may be from 0 to 3, preferably from 0 to 2, and even more preferably from 0 to 1. Note that m1 and m2 may be the same or different numbers in each naphthalene ring, and may also be the same or different numbers in different naphthalene rings.

[0025] Representative examples of the diol component represented by the above formula (1) are shown below, but the raw materials used in the above formula (1) of the present invention are not limited thereto.

[0026] Examples of the diphenylbinaphthalene type include 2,2'-bis(2-hydroxyethoxy)-3,3'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-4,4'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-5,5'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-7,7'-diphenyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-8,8'-diphenyl-1,1'-binaphthalene, and the like. Among them, 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene represented by the following formula (1-a) is preferred.

[0027] Examples of the dinaphthylbinaphthalene type include 2,2'-bis(2-hydroxyethoxy)-3,3'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-4,4'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-5,5'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-7,7'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-8,8'-di-1-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-3,3'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-4,4'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-5,5'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-6,6'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-7,7'-di-2-naphthyl-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-8,8'-di-2-naphthyl-1,1'-binaphthalene, and the like. Among these, 2,2'-bis(2-hydroxyethoxy)-6,6'-di-2-naphthyl-1,1'-binaphthalene represented by the following formula (1-b) and 2,2'-bis(2-hydroxyethoxy)-6,6'-di-1-naphthyl-1,1'-binaphthalene represented by the following formula (1-c) are preferable.

[0028]

Chemical formula

[0029]

Chemical formula

[0030]

Chemical formula

[0031] The compound having a binaphthalene skeleton of the present invention satisfies the content of palladium element in the following formula (2). 0 ≦ Pd ≦ 50 ppm (2) Preferably, it satisfies the following formula (2-1). 0 ≦ Pd ≦ 40 ppm (2-1) More preferably, it satisfies the following formula (2-2). 0 ≦ Pd ≦ 25 ppm (2-2) Even more preferably, it satisfies the following formula (2-3). 0 ≦ Pd ≦ 10 ppm (2-3) Even more preferably, it satisfies the following formula (2-4). 0 ≦ Pd ≦ 5 ppm (2-4) Particularly preferably, it satisfies the following formula (2-5). 0 ≦ Pd ≦ 3 ppm (2-5) Most preferably, it satisfies the following formula (2-6). 0 ≦ Pd ≦ 1 ppm (2-6) Exceeding the upper limit of the above range is not preferable because it adversely affects the hue of the resin using the starting alcohol represented by the formula (1) and the optical member using the same. The lower limit of the content of palladium element may be 0.01 ppm or more, 0.05 ppm or more, or 0.10 ppm or more.

[0032] Also, the purity of the compound having a binaphthalene skeleton of the present invention measured by HPLC is preferably 95% or more, more preferably 98% or more, and even more preferably 99% or more.

[0033] [Method for producing a compound having a binaphthalene skeleton] In the present invention, as a method for producing a compound having a binaphthalene skeleton, for example, dibromo-binaphthol is reacted with ethylene carbonate, and the resulting compound is reacted with phenylboronic acid or naphthylboronic acid in a reaction solvent in the presence of a base and a palladium-based catalyst.

[0034] The obtained reaction product can be treated with activated carbon or a metal removal treatment similar thereto to remove the palladium-based catalyst.

[0035] [Characteristics and Uses of Compounds Having a Binaphthalene Skeleton] Since the compound having a binaphthalene skeleton of the present invention preferably combines a binaphthalene skeleton and an aryl group, it not only has a high refractive index and heat resistance but also can reduce birefringence when made into a polymer. Heretofore, 2,2'-bis-(2-hydroxyethoxy)-1,1'-binaphthalene has been used as a compound having a binaphthalene skeleton to improve the refractive index. Although the birefringence is low with this compound, there is still room for improvement in the refractive index. In contrast, since the compound having a binaphthalene skeleton of the present invention has a diaryl group introduced into the binaphthalene skeleton, the birefringence remains low and the refractive index increases efficiently. Furthermore, since the binaphthalene ring has one or more hydroxyl groups and the entire binaphthalene compound has a plurality of hydroxyl groups, the reactivity is high. Therefore, the compound having a binaphthalene skeleton of the present invention can be used as a raw material (monomer) for various resins. For example, it can be used as a polyol component of thermoplastic resins (e.g., polyester resins, polycarbonate resins, polyester carbonate resins, polyurethane resins, etc.) and thermosetting resins (e.g., epoxy resins, phenol resins, thermosetting polyurethane resins, (meth)acrylates ((meth)acrylic acid esters), etc.). When the compound having a binaphthalene skeleton of the present invention is used as a polyol component, the resulting resin has the advantage of being able to achieve both a high refractive index and low birefringence at a high level, presumably because it has a diaryl group at the 6,6'-positions of the binaphthalene skeleton.

[0036] In addition, the compound having a binaphthalene skeleton of the present invention can efficiently prepare derivatives in a general-purpose solvent.

[0037] The melting point of the compound having a binaphthalene skeleton of the present invention can be selected from a wide range of 50 to 200 °C, preferably 70 to 180 °C, more preferably 80 to 160 °C, and still more preferably 90 to 150 °C.

Examples

[0038] Hereinafter, the present invention will be described in detail with reference to examples. However, the present invention is not limited to the following examples as long as the gist thereof is not exceeded.

[0039] In the examples, various measurements were performed as follows. (1) HPLC measurement The compound obtained in the example was measured under the following apparatus and conditions to determine the purity. Equipment used: manufactured by Waters Column: ACQUITY UPLC@BEH C18 2.1×150mm Eluent (volume): dimethylformamide: ultrapure water (0.1 wt% trifluoroacetic acid) = 70 / 30. (2) NMR measurement The compound obtained in Example 1 was measured using the following apparatus and solvent. Apparatus: JNM-AL400 (400 MHz) manufactured by JEOL Ltd. Solvent: CDCl 3 (3) ICP measurement The amount of palladium element in the compound obtained in the example was measured using the following apparatus. Equipment used: Agilent Technologies Apparatus: Agilent5100 ICP-OES (4) Refractive index (nD) Apparatus: DR-M2 Abbe refractometer manufactured by ATAGO Co., Ltd. Method: The compound obtained in the example was dissolved in dimethyl sulfoxide, and the refractive index (wavelength: 589 nm) at 25 °C was measured. The refractive index as a homopolymer was estimated using the refractive index of the solution.

[0040] [Example 1] <Step 1> 5 g (11.3 mmol) of 6,6'-dibromo-1,1'-bi-2-naphthol (hereinafter sometimes abbreviated as BN-6Br), 2.3 g (25.9 mmol) of ethylene carbonate, 0.16 g (1.9 mmol) of potassium carbonate, and 15 g of toluene were charged into a flask equipped with a stirrer, a cooler, and a thermometer, and reacted at 110°C for 5 hours. The progress of the reaction was appropriately confirmed by HPLC, and when the residual amount of BN-6Br was confirmed to be 0.1% by weight or less, the reaction was terminated. After diluting the obtained reaction mixture by adding 65 g of toluene, 8 g of a 10% by weight aqueous sodium hydroxide solution was added, and the mixture was stirred at 85°C for 1 hour, and then the aqueous layer was separated and removed. After concentrating the organic layer, it was dissolved in ethyl acetate, washed with water, and then the aqueous layer was separated and removed. Further, hexane was added and recrystallized as it was, and as a result, 3.7 g (yield 61%, purity 98.8%) of a white solid of the target 2,2'-bis(2-hydroxyethoxy)-6,6'-dibromo-1,1'-binaphthalene (hereinafter sometimes abbreviated as BN2EO-6Br) was obtained. The obtained sample was used as it was for the reaction in Step 2.

[0041] <Step 2> Under a nitrogen atmosphere, 3.5 g (6.6 mmol) of BN2EO-6Br obtained in Step 2, 2.10 g (16.5 mmol) of phenylboronic acid, 0.112 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium, 9 mL of 2M aqueous potassium carbonate solution, 33 mL of toluene, and 12 mL of ethanol were charged into a flask equipped with a stirrer, a cooler, and a thermometer, and reacted at 80 °C for 2 hours. The progress of the reaction was confirmed by HPLC as appropriate, and when the residual amount of BN2EO-6Br was confirmed to be 0.1 wt% or less, the reaction was terminated. After concentrating the obtained reaction mixture, 1M aqueous sodium hydroxide solution was added and extracted with chloroform. Activated carbon was added to the obtained organic layer and stirred for 1 hour, and after filtering off the activated carbon, the organic layer was concentrated. After concentration, purification was performed by silica gel column chromatography, and as a result, 2.6 g (yield 75%, purity 99.2%) of white crystals of the target 2,2-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene (hereinafter sometimes abbreviated as BN2EO-6Ph) were obtained. When the residual metal amount was measured by ICP, Pd was 7 ppm. In addition, the obtained BN2EO-6Ph was analyzed by 1H NMR, and it was confirmed that the target product was one in which the 6,6'-positions of the binaphthalene ring were substituted with phenyl groups (Figure 1). Furthermore, as a result of measuring the refractive index using the obtained BN2EO-6Ph, the value in terms of homopolymer was 1.70.

[0042] [Example 2] A white solid of 2,2-bis(2-hydroxyethoxy)-6,6'-di-2-naphthyl-1,1'-binaphthalene (hereinafter sometimes abbreviated as BN2EO-6(2Np)) was obtained in the same manner as in Example 1 except that the phenylboronic acid in Step 2 was changed to 2-naphthaleneboronic acid. 3.1 g (yield 75%, purity 99.2%) were obtained. When the residual metal amount was measured by ICP, Pd was 7 ppm. As a result of measuring the refractive index using the obtained BN2EO-6(2Np), the value in terms of homopolymer was 1.76.

[0043] [Example 3] Except that phenylboronic acid in Step 2 was changed to 1-naphthaleneboronic acid, the procedure was the same as in Example 1 to obtain 2.9 g of a white solid of 2,2-bis(2-hydroxyethoxy)-6,6'-di-1-naphthyl-1,1'-binaphthalene (hereinafter sometimes abbreviated as BN2EO-6(1Np)) (yield 70%, purity 99.1%). When the residual metal content was measured by ICP, Pd was 8 ppm. When the refractive index was measured using the obtained BN2EO-6(1Np), the value in terms of the homopolymer was 1.70.

[0044] [Comparative Example 1] Except that the Pd removal treatment in Step 2 was not performed by activated carbon treatment, the procedure was the same as in Example 1 to obtain 2.6 g of a pale yellow solid of BN2EO-6Ph (yield 75%, purity 99.2%). When the residual metal content was measured by ICP, Pd was 80 ppm.

[0045] [Comparative Example 2] Except that the Pd removal treatment in Step 2 was not performed by activated carbon treatment, the procedure was the same as in Example 2 to obtain 3.1 g of a pale yellow solid of BN2EO-6(2Np) (yield 75%, purity 99.2%). When the residual metal content was measured by ICP, Pd was 80 ppm.

[0046] [Comparative Example 3] Except that the Pd removal treatment in Step 2 was not performed by activated carbon treatment, the procedure was the same as in Example 3 to obtain 2.9 g of BN2EO-6(1Np) (yield 70%, purity 99.1%). When the residual metal content was measured by ICP, Pd was 80 ppm. [Industrial Applicability]

[0047] Resins using the compound having a binaphthalene skeleton of the present invention as a raw material (monomer) can be used, for example, in optical members such as films, lenses, prisms, optical disks, transparent conductive substrates, optical cards, sheets, optical fibers, optical films, optical filters, and hard coat films, and are particularly useful for lenses.

Claims

1. A method for producing a compound having a binaphthalene skeleton, which is at least one of the following formulas (1c) to (1f): reacting dibromo-binaphthol with ethylene carbonate, and reacting the resulting composition with phenylboronic acid or naphthylboronic acid in a reaction solvent in the presence of a base and a palladium-based catalyst, wherein tetrakis(triphenylphosphine)palladium is used as the palladium-based catalyst, and the content of palladium element in the resulting compound having a binaphthalene skeleton satisfies the following formula (2). 【Chemical 1】 【Chemical Formula 2】 【Chemical Formula 3】 [Chemical Formula 4] (wherein, R ３ to R ６ each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group which may contain an aromatic group having 1 to 12 carbon atoms, Ar １ represents an aromatic group which may have a substituent having 6 to 10 carbon atoms, L １ and L ２ represent an alkylene group having 1 to 12 carbon atoms, and j and k each independently represent an integer of 1 to 5.) 0.01 ≦ Pd ≦ 10 ppm (2)

2. The method for producing a compound having a binaphthalene skeleton according to Claim 1, wherein the compound having a binaphthalene skeleton is the formula (1d).

3. Ar in the formulas (1c) to (1f) above １ The method for producing a compound having a binaphthalene skeleton according to claim 1, wherein １ is a phenyl group or a naphthyl group.

4. The method for producing a compound having a binaphthalene skeleton according to Claim 1, wherein the compound having a binaphthalene skeleton is at least one of the following formulas (1-a) to (1-c). 【Chemical Formula 5】 [Chemical Formula 6] 【Chemical Formula 7】

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