JP2008063240A - Method for producing anthracene compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method of obtaining a di-substituted anthracene compound in a high yield which is a method simple in the operation of production without using a reducing agent or a heavy metal material. <P>SOLUTION: The anthracene compound is obtained, for example, by reacting a Grignard reagent of a fluorene halide with anthraquinone, and the compound of a figure is illustrated. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a method for producing an anthracene compound useful for materials for organic electroluminescent elements.

It has been disclosed that 9,10-disubstituted anthracene compounds are useful compounds as materials for organic electroluminescence devices (see Patent Document 1). Patent Document 1 discloses a method of reacting a dihalogenated anthracene and a boric acid compound in the presence of a catalyst as a production method (see Patent Document 1). However, this method requires the use of an expensive coupling catalyst. As a production method that does not use a coupling catalyst, a plurality of methods for aromatization reaction after reacting an anthraquinone compound and a Grignard reagent are disclosed. In Reference 1, anthraquinone and Grignard reagent are reacted, then reacted with ammonium chloride to synthesize 9,10-disubstituted-9,10-dihydroxyanthracene as an intermediate, and further reacted with formic acid to produce 9,10- A method for obtaining a di-substituted anthracene compound is described (see Document 1). However, in this method, formic acid must be used as a reducing agent in addition to ammonium chloride, and there is a problem that the yield is further low.
Documents 2 and 3 describe a method in which a Grignard reagent and an anthraquinone compound are reacted, then reacted with hydriodic acid, and further reacted with tin (II) chloride as a reducing agent (see Documents 2 and 3). . However, since this method uses expensive hydroiodic acid and tin (II) chloride, it is not preferable because of cost in industrial production. Furthermore, it is not preferable to use a tin compound which is a heavy metal from the viewpoint of environmental pollution.
In Reference 4, after the Grignard reagent and an anthraquinone compound are reacted, titanium (III) chloride is reacted with lithium aluminum hydride as a reducing agent to obtain the desired product (see Reference 4). However, this method uses expensive titanium (III) chloride and lithium aluminum hydride. All of the above-described methods require a reducing agent and are complicated to operate due to the use of a plurality of materials, so that they are not sufficiently satisfactory as an industrial production method. Document 5 describes a method in which methylmagnesium iodide is reacted with an anthraquinone compound and then reacted with hydrochloric acid (see Document 5). However, in this method, a product in which the α-position of anthraquinone is substituted with a chlorine atom is obtained.
WO02 / 14244 public information J. Am. Chem. Soc, 1990, 112, 2577-2581 J. Org. Chem, 1979, 44 (13), 2150-2153. T. Lett, 1977, 971-974 J. Org. Chem, 1988, 53, 345-35. J. Org. Chem, 1979, 44 (21), 3715-3717.

  An object of the present invention is to provide a high yield method as a method for producing a useful 9,10-disubstituted anthracene compound and a method having a simple production operation without using a reducing agent or a heavy metal material.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have reacted an aromatic halide Grignard reagent with an anthraquinone compound, and then reacted one or two selected from hydrochloric acid or sulfuric acid. As a result, it was found that the 9,10-disubstituted anthracene compound as the target product was obtained in high yield, and the present invention was achieved. Surprisingly, the present invention does not produce a substituent such as a chlorine atom at the α-position. In the present invention, it is not necessary to use a reducing agent or heavy metal such as tin (II) chloride, formic acid, LiALH4, etc., and the object can be obtained by using inexpensive hydrochloric acid and sulfuric acid. It has a great advantage as a low-cost method with low environmental pollution, simple operation, and low cost.
That is, the present invention
General formula (1)

（１）
［式中、Ｒ₁は炭素数３〜２５の芳香族基を表し、Ｘ₁はフッ素、塩素、臭素、ヨウ素から選ばれるハロゲン原子を表す。］で表される化合物および一般式（２）

(1)
[Wherein R ₁ represents an aromatic group having 3 to 25 carbon atoms, and X ₁ represents a halogen atom selected from fluorine, chlorine, bromine and iodine. And a compound represented by the general formula (2)

(２)
〔式中、Ｒ₂は炭素数３〜２５の芳香族基を表し、Ｘ_２はフッ素、塩素、臭素、ヨウ素から選ばれるハロゲン原子を表す。〕で表される化合物の１種または２種を、一般式（３）

(2)
[Wherein R ₂ represents an aromatic group having 3 to 25 carbon atoms, and X ₂ represents a halogen atom selected from fluorine, chlorine, bromine and iodine. Or a compound represented by general formula (3):

（３）
〔式中Ｒ₃〜Ｒ₁₀はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アルコキシ基、炭素数３〜２５の芳香族基を表す。〕で表されるアントラセン化合物を反応させ、塩酸または硫酸から選択される１種または２種の酸を用いて反応させる、ことを特徴とする一般式（４）

(3)
[Wherein R _{3 to} R ₁₀ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aromatic group having 3 to 25 carbon atoms. The anthracene compound represented by the general formula (4) is reacted with one or two acids selected from hydrochloric acid or sulfuric acid.

（４）
［式中、Ｒ₃〜Ｒ₁₀は一般式（３）中のＲ₃〜Ｒ₁₀と同じ置換基を表し、Ｒ₁₁,Ｒ₁₂は各々独立にＲ₁またはＲ₂と同じ置換基を表す。］で表されるアントラセン化合物の製造方法に関するものである。

(4)
Wherein, R ₃ to R ₁₀ in general formula (3) represents the same substituent as R ₃ to R ₁₀ in represents R _11, R ₁₂ are each independently the same substituents as R ₁ or R _2. ] It is related with the manufacturing method of the anthracene compound represented by this.

  According to the present invention, a disubstituted anthracene compound can be obtained in high yield without using a reducing agent and heavy metal material.

  In the production method of the present invention, the compound represented by the general formulas (1) and (2) is reacted with the compound represented by the general formula (3), and then one or two selected from hydrochloric acid or sulfuric acid. It is characterized by producing by reacting.

R ₁ in the general formula _(1), R ₂ in the general formula (2) is an aromatic group having 3 to 25 carbon atoms is not particularly restricted but includes aromatic group of 3-25 carbon atoms, each independently And heterocyclic rings such as phenyl group, naphthyl group, fluorenyl group, pyrenyl group, benzopyrenyl group, pentacenyl group, and other carbocyclic aromatic groups, furyl group, thienyl group, pyridyl group, benzofuranyl group, dibenzofuranyl group, carbazolyl group, etc. Represents an aromatic group. Further, this aromatic group is an alkyl group having 1 to 16 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, a substituted amino group having 1 to 24 carbon atoms, a carbocyclic aromatic group having 6 to 25 carbon atoms, or 3 carbon atoms. It may be substituted with ~ 25 heterocyclic aromatic groups.

R ₃ to ₁₀ in the general formulas (3) and (4) represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aromatic group having 3 to 25 carbon atoms. Although not particularly limited, the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, the alkyl group is an alkyl group having 1 to 16 carbon atoms, the alkoxy group is an alkoxy group having 1 to 16 carbon atoms, or 3 to 3 carbon atoms. 25 aromatic groups are phenyl, naphthyl, fluorenyl, pyrenyl, benzopyrenyl, pentacenyl and other carbocyclic aromatic groups, furyl, thienyl, pyridyl, benzofuranyl, dibenzofuranyl, carbazolyl Represents a heterocyclic aromatic group such as a group;
R ₃ to ₁₀ in the general formula (4) are each connected to two or more, and may form a hydrocarbon ring or a heterocyclic ring. However, R ₃ to ₁₀ must not be directly bonded to R ₁₁ and R ₁₂ .

The compound represented by the general formula (1) and the compound represented by the general formula (2) may be produced from another compound when used. Specifically, it is produced by reacting an aryl halide such as R ₁ -X ₁ or R ₂ -X ₂ with magnesium using a known method for producing a Grignard reagent. Furthermore, a reaction mass obtained by reacting an aryl halide with magnesium may be used as it is for the reaction with the compound of the general formula (3).

  In producing the compounds of the general formulas (1) and (2), a solvent may or may not be used, but preferably acyclic ether such as dimethyl ether or diethyl ether, tetrahydrofuran, 1, 4 -Use cyclic ethers such as dioxane. More preferably, the water in the solvent is removed as much as possible. Moisture reacts with the compounds of general formulas (1) and (2) and causes a decrease in yield.

  The reaction of the compounds of general formulas (1) and (2) and the compound of general formula (3) may or may not use a solvent. The solvent is preferably a solvent that does not react with the Grignard reagent, for example, acyclic ether such as dimethyl ether and diethyl ether, cyclic ether such as tetrahydrofuran and 1,4-dioxane, aliphatic hydrocarbons such as hexane and heptane, toluene, naphthalene and the like It is preferable to use the aromatic attribute hydrocarbons. When the compounds of the general formulas (1) and (2) are produced from an aryl halide, the solvent can be used as a reaction solvent with (3).

In the present invention, the compounds of the general formulas (1) and (2) are reacted with the compound of the general formula (3) and then reacted with one or two of hydrochloric acid and sulfuric acid (aromatization reaction). A compound of general formula (4) is produced.
The aromatization reaction may or may not use a solvent. Moreover, the solvent which made the compound of General formula (1) and (2) react with the compound of General formula (3) can be used as it is. After reacting with the compound of the general formula (3) and subsequently reacting with one or two kinds of hydrochloric acid and sulfuric acid, the reaction mass is charged with one or two kinds of hydrochloric acid or sulfuric acid. The charging method may be performed continuously by dropping or the like, or may be charged in a lump.
As hydrochloric acid to be used, 1 to 36% hydrochloric acid water or hydrogen chloride gas is used. Preferably it is 10-36% hydrochloric acid water.
The sulfuric acid used is 1 to 98% sulfuric acid, preferably 5 to 50% sulfuric acid water.

In the present invention, the α-substituted product as in Reference 5 does not occur. This is presumed that R ₁ and R ₂ in the general formula (1) and the general formula (2) are aromatic groups. Specifically, since there is no hydrogen at the position corresponding to the α-position, the main reaction (reduction and dehydration) is prioritized because the dehydration and hydrochloric acid addition of the hydrogen corresponding to the α-position does not occur during the reaction with hydrochloric acid. I guess.

  The reaction temperature during the aromatization reaction is not limited, but is preferably -20 ° C to 120 ° C. More preferably, it is 0 degreeC-100 degreeC, and a favorable reaction rate and high target object selectivity can be obtained.

  After the aromatization reaction is completed, the compound of general formula (4), which is the target product, is isolated using a known method. Although not limited, when the compound of General formula (4) crystallizes and precipitates in the reaction mass, it can obtain by filtering. In the dissolved state, it may be obtained by filtering after depositing crystals by cooling or charging a solvent having low solubility. A solvent or a target product can also be obtained by distillation or sublimation.

  According to the method of the present invention, the target disubstituted anthracene compound can be obtained in high yield. High yield refers to 75 mol% or more based on the anthraquinone compound. When the method according to the present invention is used, a high yield can be obtained because of the high reaction selectivity for the target product and the high target product recovery rate in the removal operation. When the conventional method of reacting with a Grignard reagent and then using a reducing agent is applied, it is necessary to remove excess reducing agent and reducing agent-inducing substance, which is a complicated removal operation, and a high yield is obtained. Have difficulty.

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples.
In addition, the measurement of the purity of the compound in which the purity in each following Example was described was based on the high performance liquid chromatography (henceforth "HPLC").
The conditions for HPLC analysis are as follows.
Column: YMC-Pack ODS-A A-312 manufactured by YMC Co., Ltd.
Column oven temperature: 40 ° C
Eluent: THF: methanol ratio = 5: 95 mixed solvent Detection wavelength: 254 nm

[Synthesis Example 1]
Synthesis of Compound (5) 19,4.2 g of 9,9-dimethylfluorene was dissolved in 1000 g of o-dichlorobenzene, 162.4 g of iodine monochloride was charged, and the reaction mass was kept at 100 ° C. for 4 hours. After removing o-dichlorobenzene by distillation under reduced pressure, 300 g of toluene was charged and stirred at 30 ° C. for 3 hours. Crystals in the reaction mass were removed by vacuum filtration and washed with 100 g of methanol. The crystals were dried to obtain 144.1 g of a compound of the following formula (5). As a result of analysis by HPLC, the purity was 98%, and the yield was 44%. The elemental analysis results and FD-MS measurement results of the compound of the formula (5) are as follows, and it was confirmed that the compound was the compound of the formula (5).
Results of elemental analysis CHI FD-MS
(M / z)
Compound (5) 56.28 4.10 39.62 320
Theoretical value (%) 56.27 4.09 39.64 320

（５）

(5)

Synthesis of Compound (6) 1.9 g of magnesium was charged into 10.0 g of tetrahydrofuran, and the temperature was adjusted to 65 ° C. A solution prepared by dissolving 24.0 g of compound (5) in 72.0 g of tetrahydrofuran was charged and kept at 65 ° C. for 2 hours. Next, 7.1 g of anthraquinone was charged and kept at 65 ° C. for 3 hours. The reaction mass was charged with 31.2 g of 18% aqueous hydrochloric acid and kept at 65 ° C. for 2 hours. White crystals were precipitated on the reaction mass. The crystals were removed by filtration, washed with methanol and dried. 15.3 g of the following compound (6) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 77%. The elemental analysis results and FD-MS measurement results of the compound of the formula (6) are as follows, and it was confirmed that the compound was the compound of the formula (6).
Elemental analysis results C H FD-MS
(M / z)
Compound (6) 93.89 6.11 562
Theoretical value (%) 93.91 6.09 562

（６）

(6)

Synthesis of Compound (7) 1.9 g of magnesium was charged into 10.0 g of tetrahydrofuran, and the temperature was adjusted to 65 ° C. A solution prepared by dissolving 15.3 g of iodobenzene in 72.0 g of tetrahydrofuran was charged, and kept at 65 ° C. for 2 hours. Next, 7.1 g of anthraquinone was charged and kept at 65 ° C. for 3 hours. The reaction mass was charged with 31.2 g of 18% aqueous hydrochloric acid and kept at 65 ° C. for 2 hours. White crystals were precipitated on the reaction mass. The crystals were removed by filtration, washed with methanol and dried. 10.1 g of the following compound (7) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 85%. The elemental analysis results and FD-MS measurement results of the compound of formula (7) are as follows, and it was confirmed that the compound was of the formula (7).
Elemental analysis results C H FD-MS
(M / z)
Compound (7) 94.49 5.51 330
Theoretical value (%) 94.51 5.49 330

（７）

(7)

Synthesis of Compound (7) 37.5 ml of Phenyl Magnesium Iodide (concentration 2 Mol / L ethyl ether solution) was charged, and 7.1 g of anthraquinone was charged. The temperature was raised and maintained at 35 ° C. for 3 hours. The reaction mass was charged with 31.2 g of 18% hydrochloric acid and kept at 35 ° C. for 2 hours. White crystals were precipitated on the reaction mass. The crystals were removed by filtration, washed with methanol and dried. 10.9 g of the above compound (7) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 92%. The elemental analysis results and FD-MS measurement results of the compound of formula (8) are as follows, and it was confirmed that the compound was of the formula (7).
Elemental analysis results C H FD-MS
(M / z)
Compound (7) 94.53 5.47 330
Theoretical value (%) 94.51 5.49 330

Synthesis of Compound (8) 1.0 g of magnesium was charged into 10.0 g of tetrahydrofuran, and the temperature was adjusted to 65 ° C. A solution prepared by dissolving 12.0 g of compound (5) in 36.0 g of tetrahydrofuran was charged, and kept at 65 ° C. for 2 hours. The reaction mass was charged with 7.1 g of anthraquinone and kept at 65 ° C. for 2 hours. 18.8 ml of phenylmagnesium iodide (concentration: 2 mol / L ethyl ether solution) manufactured by Tokyo Chemical Industry Co., Ltd. was charged and kept at 65 ° C. for 2 hours. The reaction mass was charged with 31.2 g of 18% aqueous hydrochloric acid and kept at 65 ° C. for 2 hours. White crystals were precipitated on the reaction mass. The crystals were removed by filtration, washed with methanol and dried. 13.1 g of the following compound (8) was obtained. As a result of analysis by HPLC, the purity was 95%, and the yield was 82%. The elemental analysis results and FD-MS measurement results of the compound of formula (8) are as follows, and it was confirmed that the compound was of the formula (8).
Elemental analysis results C H FD-MS
(M / z)
Compound (8) 94.12 5.88 446
Theoretical value (%) 94.13 5.87 446

（８）

(8)

Synthesis of Compound (9) The same procedure as in Example 1 was conducted except that 9.4 g of 1,5-dichloroanthraquinone was used instead of 7.1 g of anthraquinone. 17.9 g of the following compound (9) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 80%. The elemental analysis results and FD-MS measurement results of the compound of the formula (9) are as follows, and it was confirmed that the compound was the compound of the formula (9).

Elemental analysis results C H Cl FD-MS
(M / z)
Compound (9) 86.64 5.14 11.23 630
Theoretical value (%) 86.67 5.11 11.23 630

（９）

(9)

Synthesis of Compound (10) The same procedure as in Example 1 was conducted except that 8.8 g of 1,2-benzoanthraquinone was used instead of 7.1 g of anthraquinone. 17.8 g of the following compound (10) was obtained. As a result of analysis by HPLC, the purity was 95%, and the yield was 81%. The elemental analysis results and FD-MS measurement results of the compound of the formula (10) are as follows, and it was confirmed that the compound was the compound of the formula (10).

Elemental analysis results C H FD-MS
(M / z)
Compound (10) 94.09 5.91 612
Theoretical value (%) 94.08 5.92 612

(１０)

(10)

Synthesis of Compound (11) The same procedure as in Example 1 was conducted except that 9.0 g of 2-tertbutylanthraquinone was used instead of 7.1 g of anthraquinone. 18.8 g of the following compound (11) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 86%. The elemental analysis results and FD-MS measurement results of the compound of the formula (11) are as follows, and it was confirmed that the compound was the compound of the formula (11).

Elemental analysis results C H FD-MS
(M / z)
Compound (11) 93.17 6.83 618
Theoretical value (%) 93.16 6.84 618

(１１)

(11)

Synthesis of Compound (12) The same procedure as in Example 3 was performed except that 9.1 g of 2,6-dimethoxyanthraquinone was used instead of 7.1 g of anthraquinone. 12.9 g of the following compound (12) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 93%. The elemental analysis results and FD-MS measurement results of the compound of the formula (12) are as follows, and it was confirmed that the compound was the compound of the formula (12).

Elemental analysis results C H FD-MS
(M / z)
Compound (12) 86.15 5.68 390
Theoretical value (%) 86.13 5.68 390

（１２）

(12)

[Comparative Example 1]
Synthesis of Compound (7) A flask charged with 7.1 g of anthraquinone was charged with 37.5 ml of Tokyo Chemicals phenylmagnesium bromide (concentration 2 mol / L ethyl ether solution). The temperature was raised and the reflux state was maintained for 3 hours. The reaction mass was discharged into 400 g of a saturated aqueous solution of ammonium chloride and purified by column chromatography packed with alumina to obtain 2.5 g of crystals. The crystals were charged with 470 ml of formic acid, heated and kept in the refluxed state for 18 hours. Formic acid was distilled off, column chromatography packed with alumina was performed, and recrystallization was performed using benzene and hexane. 0.8 g of the above compound (7) was obtained. As a result of analysis by HPLC, the purity was 96%, and the yield was 6.8%. The elemental analysis results and FD-MS measurement results of the compound of formula (7) are as follows, and it was confirmed that the compound was of the formula (7).

Elemental analysis results C H FD-MS
(M / z)
Compound (7) 94.52 5.48 330
Theoretical value (%) 94.51 5.49 330

[Comparative Example 2]
Synthesis of Compound (13) A Grignard reagent was prepared by reacting 150 g of iodobenzene with 12 g of magnesium in 1 L of diethyl ether. This solution was added dropwise to a mixture of 6.6 g of 2-benzoanthoaquinone and 2 L of anhydrous benzene. The reaction mass was heated and kept at reflux for 10 hours. 500 ml of saturated aqueous ammonium chloride solution and 1 L of ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate, and crystals obtained by removing the solvent were obtained. The crystals were dissolved in 1 L of ethyl acetate, and hydrochloric acid gas was blown in over 40 minutes while keeping the temperature of the solution at 0 ° C. After aging at the same temperature for 2 hours, the solvent was distilled off. The residue was dissolved in 200 ml of tetrahydrofuran, and charged in a flask in which 2 g of LiAlH4 was dispersed in 1.5 L of diethyl ether at room temperature. One hour later, a saturated aqueous solution of ammonium chloride was added, the diethyl ether layer was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain crystals. The crystals were purified by column chromatography packed with silica gel to obtain 3.1 g of compound (13). As a result of analysis by HPLC, the purity was 95%, and the yield was 30%. The elemental analysis results and FD-MS measurement results of the compound of the formula (13) are as follows, and it was confirmed that the compound was the compound of the formula (13).

Elemental analysis results C H FD-MS
(M / z)
Compound (13) 94.69 5.31 380
Theoretical value (%) 94.70 5.30 380

（１３）

(13)

[Comparative Example 3]
Synthesis of Compound (7) 6.2 g of anthraquinone was mixed with 400 ml of benzene, and 60 ml of a diethyl ether solution (concentration: 3 mol / L diethyl ether solution) of phenyl magnesium bromide manufactured by Aldrich was added and kept in a reflux state for 16 hours. 500 ml of saturated aqueous ammonium chloride solution and 1 L of ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off to give a residue. The residue was pulverized in 100 ml of benzene and washed with 200 ml of hexane to obtain crystals. 350 ml of diethyl ether was charged with 19.6 g of tin (II) chloride and 17.3 g of concentrated hydrochloric acid, and the above crystals were added over 5 minutes, followed by stirring for 20 minutes. This reaction mass was purified by column chromatography packed with alumina, and recrystallized with a mixed solvent of ethanol and dichloromethane to obtain 2.0 g of Compound (7). As a result of analysis by HPLC, the purity was 94%, and the yield was 18.9%. The elemental analysis results and FD-MS measurement results of the compound of formula (7) are as follows, and it was confirmed that the compound was of the formula (7).
Elemental analysis results C H FD-MS
(M / z)
Compound (7) 94.50 5.50 330
Theoretical value (%) 94.51 5.49 330

  According to the production method of the present invention, a useful disubstituted anthracene compound can be easily obtained in a high yield. There is no need to use materials containing reducing agents and heavy metals.

Claims (4)

General formula (1)

(1)
[Wherein R ₁ represents an aromatic group having 3 to 25 carbon atoms, and X ₁ represents a halogen atom selected from fluorine, chlorine, bromine and iodine. And a compound represented by the general formula (2)

(2)
[Wherein R ₂ represents an aromatic group having 3 to 25 carbon atoms, and X ₂ represents a halogen atom selected from fluorine, chlorine, bromine and iodine. Or a compound represented by general formula (3):

(3)
[Wherein R _{3 to} R ₁₀ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aromatic group having 3 to 25 carbon atoms. The anthracene compound represented by the general formula (4) is reacted with one or two acids selected from hydrochloric acid or sulfuric acid.

(4)
Wherein, R ₃ to R ₁₀ in general formula (3) represents the same substituent as R ₃ to R ₁₀ in represents R _11, R ₁₂ are each independently the same substituents as R ₁ or R _2. ] The manufacturing method of the anthracene compound represented by this. The method according to claim 1, wherein R ₁ and / or R ₂ is a fluorenyl group. The production method according to claim 1, wherein X ₁ is an iodine atom and X ₂ is an iodine atom. A compound of general formula (1) and / or general formula (2) is produced from an aromatic iodide having 3 to 25 carbon atoms and magnesium, and subsequently reacted with a compound of general formula (3) Item 4. The production method according to any one of Items 1 to 3.