JPH05178810A - Unsymmetrical 9-cyanostyryl-10-styrylanthracene derivative and its production - Google Patents

Abstract

PURPOSE:To obtain a new unsymmetrical 9-cyanostyryl-10-styrylanthracene derivative extremely useful as an organic electric field luminous element having high luminance. CONSTITUTION:An unsymmetrical 9-cyanostyryl-10-styrylanthracene derivative extremely useful as an organic electric field luminous element of formula I (R<1> and R<2> are substituted or nonsubstituted carbon cyclic aromatic ring, substituted or nonsubstituted heterocyclic aromatic ring and R<2> is H, CN or alkyl) such as a compound of formula II. The compound is obtained by formylating 9-cyanostyrylanthracene of formula III to give a compound of formula IV and reacting this compound with a compound of formula V [X is PO(OR<3>)2 or P(R<4>)3Y; R<3> is alkyl or aryl; R<4> is aryl; Y is halogen].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel asymmetric 9-cyanostyryl-10-styrylanthracene derivative useful as an organic electroluminescent device, and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, as an organic electroluminescent device, Japanese Patent Laid-Open No. 3-33184 discloses a distyrylbenzene derivative. However, the distyryl derivative is still not sufficiently satisfactory in terms of brightness.

[0003]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel asymmetric 9-cyanostyryl-10-styrylanthracene derivative which is useful as a high-luminance organic electroluminescent device, and a method for producing the same. ..

[0004]

According to the present invention, the following chemical formula 1

[Chemical 1] An asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by the following formula:

[Chemical 2] 9-cyanostyrylanthracene represented by

[Chemical 3] A compound represented by

[Chemical 4] The following chemical formula 1 characterized by reacting with a compound represented by

[Chemical 1] A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by

[Chemical 5] The compound represented by

Embedded image R ¹ —CHO (wherein R ^{1 is a} substituted or unsubstituted carbocyclic aromatic ring,
It represents a substituted or unsubstituted heterocyclic aromatic ring. ) With an aldehyde compound represented by the following formula

[Chemical 7] Or a reaction with an aldehyde represented by the chemical formula 7 and then with an aldehyde represented by the chemical formula 6 below.

[Chemical 8] A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by

[Chemical 9] The 9,10-anthracene dialdehyde represented by
Following 4

[Chemical 4] By reacting with a compound represented by

[Chemical 10] By reacting with a compound represented by the above formula or by reacting with a compound represented by the above formula
The following chemical formula 1 characterized by reacting with a compound represented by

[Chemical 1] There is provided a method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by:

[Chemical 5] The compound represented by

Embedded image R ¹ —CHO (wherein R ^{1 is a} substituted or unsubstituted carbocyclic aromatic ring,
And a substituted or unsubstituted heterocyclic aromatic ring. ) An aldehyde compound represented by

[Chemical 7] The following chemical formula 8 characterized by reacting with an aldehyde compound represented by

[Chemical 8] A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by

Surprisingly, it was found that the asymmetric 9-cyanostyryl-10-styrylanthracene derivative of the present invention has excellent properties as an electroluminescent device such as brightness, and the present invention has been completed.

Asymmetric 9-Cyanostyryl-10 of the Invention
-A styrylanthracene derivative is represented by the following chemical formula 1 as described above.

[Chemical 1] It is represented by. The substitution position of the cyano group is the ortho position, the meta position, or the para position, and the para position is particularly preferable.

Further, examples of the carbocyclic aromatic ring of R ¹ and R ² include a phenyl group, a biphenyl group and a naphthyl group, and examples of the heterocyclic aromatic ring include the following groups. .. Pyridyl group, pyrimidyl group, pyrazinyl group, triazinyl group, furanyl group, pyrrolyl group, thiophenyl group,
Quinolyl group, coumarinyl group, benzofuranyl group, benzimidazolyl group, benzoxazolyl group, dibenzofuranyl group, benzothiophenyl group, dibenzothiophenyl group, indolyl group, carbazolyl group, pyrazolyl group, imidazolyl group, oxazolyl group, isoxazolyl group Base,
Thiazolyl group, indazolyl group, benzothiazolyl group,
Pyridazinyl group, cinnolyl group, quinazolyl group, quinoxalyl group.

R¹, R²The aromatic ring represented by has a substituent
And the following may be mentioned as the substituent.
be able to. (1) Halogen atom, trifluoromethyl group, cyano
Group, nitro group (2) alkyl group; preferably C₁~ C₂₀Especially C₁~
C₁₂A straight or branched chain alkyl group of
The alkyl group is further a hydroxyl group, a cyano group, C₁~ C₁₂A
Lucoxy group, phenyl group or halogen atom, C₁~ C
₁₂Alkyl group or C₁~ C₁₂Set with the alkoxy group of
It may contain a substituted phenyl group. (3) Alkoxy group (-OR^Five); R^FiveIs defined in (2)
Represents an alkyl group. (4) Aryloxy group; phenyl as an aryl group
Group, naphthyl group, and these are C₁~ C₁₂The al
Coxy group, C₁~ C₁₂Alkyl group or halogen atom
May be contained as a substituent. (5) Alkylthio group (-SR^Five); R^FiveIs defined in (2)
Represents an alkyl group. Acyl groups such as alkyl group, acetyl group, benzoyl group, etc.
Represents an aryl group, and the aryl group is, for example,
Examples thereof include a nyl group, a biphenyl group and a naphthyl group.
These are C₁~ C₁₂Alkoxy group of C₁~ C₁₂The alkyl
A group or a halogen atom may be contained as a substituent.
In addition, like the pipedyl group and morpholyl group, R⁶And R⁷Is
You may form a ring in cooperation with an elementary atom. Urolydyl group
Form a ring in cooperation with the carbon atom on the aryl group such as
Is also good. (7) Alkoxycarbonyl group (-COOR⁸); R⁸Is
The alkyl group defined in (2) or the alkyl group defined in (4).
Represents a reel base. R⁶, R⁷And R⁸Represents the meaning defined above. However
R⁶And R⁷In the ring jointly with the carbon atom on the aryl group
Except when forming. (9) Methylenedioxy group or methylenedioxy group, etc.
Alkylenedioxy group or alkylenedithio group

The asymmetric 9- of the present invention represented by the above chemical formula 1
The cyanostyryl-10-styrylanthracene derivative can be produced, for example, by the following novel method. That is,

[Chemical 2] The 9-cyanostyrylanthracene represented by is easily formylated by, for example, the Vilsmeier method or a method using dichloromethyl ether (4th edition, Experimental Chemistry Course, Vol. 21, page 110, Maruzen Co., Ltd.) (step A), below

[Chemical 3] The aldehyde represented by

[Chemical 4] (Wherein R ¹ , R ² and X are as described above) are reacted (Step B) to produce an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by the above chemical formula 1. be able to.

The formylation reaction (step A) of 9-cyanostyrylanthracene represented by the above chemical formula 2 is carried out, for example, with V
In the ilsmeier method, N, N-dimethylformamide and phosphorus oxychloride are allowed to act to form a Vilsmeier complex, which is reacted with 9-cyanostyrylanthracene represented by the above chemical formula 2 and then hydrolyzed to give the above chemical formula 3. An aldehyde represented by can be obtained. Other reagents include N-methylformanilide and N-methylformanilide.
-Formylmorpholine and the like may be used in combination with thionyl chloride, oxalyl chloride and the like. As the solvent, any solvent that can partially or completely dissolve 9-cyanostyrylanthracene represented by the above chemical formula 2 can be used, but N, N-dimethylformamide, which can also be used as a reagent, is most suitable. Suitably the reaction temperature is from room temperature to about 100 ° C. The hydrolysis reaction can be carried out with an alkaline aqueous solution of sodium hydroxide, potassium hydroxide or the like, and the desired compound 3 can be obtained by recrystallization.
An aldehyde represented by can be obtained.

The reaction between the compound represented by the chemical formula 3 and the compound represented by the chemical formula 4 (step B) can be carried out in the presence of an alkaline condensing agent. Such condensing agents include alkali metal or alkaline earth metal hydroxides, hydrides, alkoxides, and amides. Particularly useful are sodium methylate, sodium ethylate, potassium t-butoxide, sodium hydroxide and potassium hydroxide. The amount of condensing agent used can vary widely, but is equimolar to 1.2.
The double mole is most suitable. As the solvent, any solvent can be used as long as it can partially or completely dissolve the aldehyde represented by the above chemical formula 3, but especially an aprotic polar solvent such as N, N-dimethylformamide,
N, N-diethylformamide, and dimethyl sulfoxide are suitable. The reaction temperature is 0 to 100 ° C., especially 0 to
50 ° C is suitable.

As another novel method, the following chemical formula 5

[Chemical 5] (Wherein, X is as described above)

## STR00006 ## An aldehyde represented by R ¹ --CHO (wherein R ¹ is as described above) is reacted (step C ₁ ) and then

[Chemical 7] By reacting with an aldehyde compound represented by the formula (step D ₁ ) or by reacting the compound represented by the chemical formula 5 with the aldehyde represented by the chemical formula 7 (step D ₁ ).
₂ ) and then reacting with the aldehyde represented by the above Chemical formula 6 (step C ₂ ), the R ² group in the asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by the above Chemical formula 1 is a hydrogen atom. Compound (8 above)
The compound represented by) can be produced.

As another new method, the following chemical formula 9

[Chemical 9] The 9,10-anthracene dialdehyde represented by
Following 4

[Chemical 4] (Wherein R ¹ , R ² and X are as described above) and reacted (step E ₁ )

[Chemical 10] By reacting with a compound represented by the formula (wherein X is as described above) (step F ₁ ) or
The asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by the chemical formula 1 by reacting with the compound represented by the chemical formula (Step F ₂ ) and then by reacting with the compound represented by the chemical formula 4 (Step E ₂ ). Can be manufactured.

As another new method, the following chemical formula 5

[Chemical 5] The compound represented by

Embedded image An aldehyde represented by R ¹ —CHO (wherein R ¹ is as described above) and the following chemical formula 7

[Chemical 7] By reacting represented by aldehyde compound in (Step G), the inner R ² asymmetric 9-cyanostyryl-10-styryl anthracene derivative represented by Formula 1
A compound in which the group is a hydrogen atom (a compound represented by the above chemical formula 8) can be produced.

The compound represented by the chemical formula 5 and the compound represented by the chemical formula 6
Or / and a reaction with a compound represented by Chemical formula 7 (steps C ₁ , D ₁ , C ₂ , D ₂ , G), and a compound represented by Chemical formula 9 and a compound represented by Chemical formula 4 or Chemical formula 10 In each reaction of the above reaction (steps E ₁ , F ₁ , E ₂ , F ₂ ) can be carried out in the presence of the alkaline condensing agent used in the above step B. Although the amount of the condensing agent to be used can be greatly changed, an equimolar amount or less is suitable particularly in each of the steps C ₁ , D ₁ , E ₁ and F ₁ . In addition, in these steps, the next reaction can be carried out after isolation of the intermediate, but it is preferable to carry out the next reaction without isolation. As the solvent, any solvent can be used as long as it can partially or completely dissolve the compound represented by the above Chemical formula 5 or Chemical formula 9. Such solvents include cyclohexane, toluene, chlorobenzene, formamide, N, N-dimethylformamide,
N-methylpyrrolidone, acetonitrile, dimethyl sulfoxide, isopropanol and the like are suitable. A reaction temperature of 0 to 100 ° C, particularly 0 to 50 ° C is suitable.

The above-mentioned Chemical formula 2, Chemical formula 4, Chemical formula 5, Chemical formula 6, Chemical formula 7, Chemical formula 9 used as starting materials in the production method of the present invention.
And the compound represented by Chemical formula 10 is publicly known, or can be easily produced according to publicly known methods. The aldehyde represented by the chemical formula 3 obtained as an intermediate product in the production method of the present invention is a novel compound.

Asymmetry 9 represented by the above chemical formula 1 of the present invention
The -cyanostyryl-10-styrylanthracene derivative is particularly excellent as a constituent component of an organic electroluminescent device. For example, a thin film is formed by a vacuum vapor deposition method, a solution coating method, or the like, and an element is obtained by sandwiching it with an anode and a cathode. You can

Asymmetric 9- represented by the following chemical formula 1 of the present invention
Specific examples of the cyanostyryl-10-styrylanthracene derivative are shown in Table 1 below.

[Chemical 1]

[Table 1- (1)]

[Table 1- (2)]

[Table 1- (3)]

[0019]

[Examples] The following examples further illustrate the methods for preparing the compounds of the present invention.

Example 1 (Production of Intermediate) 52.1 ° C. in 62.1 gr of N, N-dimethylformamide
It takes about 1 hour at the temperature of 65.2 gr of phosphorus oxychloride
To produce a Vilsmeier complex. To this was added 25.96 gr of 9- (P-cyanostyryl) anthracene (P-substituted compound represented by Chemical formula 2). After reacting at room temperature for 1 hour, the temperature was gradually raised and reacted at 60 to 65 ° C. for 3 hours. After standing overnight, the reaction solution was poured into about 800 ml of ice water, made alkaline with sodium hydroxide aqueous solution, and an orange precipitate formed. Was collected by filtration. After washing with water and drying, recrystallization was performed twice with a dioxane-toluene mixed solvent to obtain 21.85 gr of orange needle crystals (yield 76.1%). Melting point: 244.5 to 246.5 ° C. Infrared absorption spectrum (KBr tablet method) 2240 cm ⁻¹ ; belonging to cyano group 1680 cm ⁻¹ ; belonging to formyl group

[Table 2] From the above results, it was confirmed that an aldehyde represented by the following chemical formula 11 (p-substituted product represented by the chemical formula 3) was obtained.

[Chemical 11]

Example 2 3.33 gr of the aldehyde represented by the chemical formula 11 prepared in Example 1 and the following chemical formula 12

[Chemical 12] 3.15 gr of the phosphonate represented by was dissolved in 70 ml of N, N-dimethylformamide. 7-1
At a temperature of 0 ° C., 2.31 gr of a methanol solution of sodium methylate (28 wt%) was required for about 30 minutes. The reaction product gradually precipitated as crystals. After reacting at room temperature for 6 hours, the reaction solution was poured into about 400 ml of water. The produced yellow fine crystals were collected by filtration, washed with water and dried to obtain 4.20 gr of a crude product. Recrystallization was performed twice from chlorobenzene using activated carbon to obtain 2.76 gr of orange-yellow needle crystals (yield 64.7%). Melting point: 300 ° C. or higher Infrared absorption spectrum (KBr tablet method) 2230 cm ⁻¹ ; belonging to cyano group

[Table 3] From the above results, it was confirmed that the compound represented by the following Chemical formula 13 (Compound No. 5 in Table 1) was obtained.

[Chemical 13]

Examples 3 to 7 The target compound was obtained in the same manner as in Example 2 except that the phosphonate and the recrystallization solvent were changed to those shown in Table 4 below.

[Table 4]

Example 8 To 60 ml of N, N-dimethylformamide, 1.46 gr of potassium t-butoxide was added under ice cooling. Furthermore,

[Chemical 14] A solution prepared by dissolving 2.91 gr of the phosphonate represented by the above in 10 ml of N, N-dimethylformamide was added dropwise at a temperature of 6 to 8 ° C over about 20 minutes. To the obtained orange-yellow solution, 3.33 gr of the aldehyde represented by the chemical formula 11 prepared in Example 1 was added at a temperature of 6 to 8 ° C over about 45 minutes. After reacting at room temperature for 1 day, about 400
The reaction solution was poured into ml of water. The produced yellow fine crystals were collected by filtration, washed with water and dried to obtain 3.62 gr of a crude product. Recrystallization was performed 3 times from toluene using activated carbon to obtain 0.98 gr of yellow needle crystals (yield 23.2%). Melting point: 263.5 to 265.5 ° C. Infrared absorption spectrum (KBr tablet method) 2230 cm ⁻¹ ; belonging to cyano group

[Table 5] From the above results, the compound No. It was confirmed that 9 was obtained.

Example 9 The desired compound was obtained in the same manner as in Example 8 except that the phosphonate and the recrystallization solvent were changed to those shown in Table 6 below.

[Table 6]

Example 10 below

[Chemical 15] 4.78 gr of phosphonate represented by

[Chemical 16] 1.20 gr of the aldehyde represented by was dissolved in 80 ml of N, N-dimethylformamide. 8 to 10
A solution of sodium methylate in methanol (2
(8 wt%) 1.93 gr was added dropwise over about 10 minutes. After reacting at about 10 ° C. for 30 minutes,

[Chemical 17] 1.44 gr of aldehyde represented by
2.31 gr of a methanol solution of sodium methylate (28 wt%) was added dropwise at a temperature of ~ 9 ° C over about 15 minutes. After reacting for 6 hours at room temperature, the reaction solution was poured into about 400 ml of ice water. The produced yellow precipitate was collected by filtration, washed with water and dried to obtain a yellow crude product. After purification by column chromatography (silica gel / toluene), it was recrystallized from toluene to give yellow needle crystals 0.77 gr.
(Yield 18.4%) was obtained. Melting point: 263.5 to 265.5 ° C. Infrared absorption spectrum (KBr tablet method) 2230 cm ⁻¹ ; belonging to cyano group (same as spectrum obtained in Example 8) From the above results, the compound No. 1 in Table 1 was obtained. It was confirmed that 9 was obtained.

Example 11 below

[Chemical 9] 9.10-anthracene dialdehyde represented by 2.
34gr and the following 18

[Chemical 18] 2.28 gr of phosphonate represented by was dissolved in 80 ml of N, N-dimethylformamide. 7 to 9
A solution of sodium methylate in methanol (2
(8 wt%) 1.93 gr was added dropwise over about 15 minutes. After reacting at about 10 ° C. for 30 minutes,

[Chemical 19] 2.78 gr of the phosphonate represented by the formula (3) was added thereto, and 2.31 gr of a methanol solution of sodium methylate (28% by weight) was added dropwise thereto at a temperature of 7 to 9 ° C over about 15 minutes. After reacting at room temperature for 5 hours, the reaction solution was poured into about 400 ml of ice water. The produced yellow precipitate was collected by filtration, washed with water and dried to obtain a yellow crude product. After purification by column chromatography (silica gel / toluene),
Recrystallized from toluene, yellow needle crystals 1.26gr
(Yield 31.0%) was obtained. Melting point: 252.0 to 253.0 ° C. Infrared absorption spectrum (KBr tablet method) 2220 cm ⁻¹ ; belonging to cyano group (same as spectrum obtained in Example 3) From the above results, the compound No. It was confirmed that 1 was obtained.

Example 12 16 ml of N, N-dimethylformamide, ethanol 2
ml, t-butoxysite potassium 1.35 gr,
With mixing and stirring at about 5 ° C.,

[Chemical 15] 2.39 gr of the phosphonate represented by is added, 8 ml of N, N-dimethylformamide and 1 part of ethanol are added.
Dissolved in a mixed solvent of ml

[Chemical 17] And 0.79 gr of the aldehyde represented by

[Chemical 20] 0.64 gr of the aldehyde represented by was added dropwise over about 20 minutes. Reaction products gradually began to precipitate. After reacting at room temperature for 5 hours, the reaction solution was poured into about 400 ml of water. The produced yellow precipitate was collected by filtration, washed with water and dried to obtain a crude product. Recrystallize with dioxane, concentrate the recrystallized mother liquor, redissolve in 700 form, purify by column chromatography (silica gel / 700 form), then recrystallize from a mixed solvent of toluene / ethanol, and finally with ethyl acetate. Was recrystallized from the above to obtain 0.02 gr of yellow crystals (yield 1%). Melting point: 2277.7-280.4 ° C. Infrared absorption spectrum (KBr tablet method) 2220 cm ⁻¹ ; Attribution to vC≡N 970 cm ⁻¹ ; Attribution to δCH═CH (trans)

[Table 7] From the above results, the compound No. It was confirmed that 17 was obtained.

[Chemical 21]

Example 13 15 ml of n, N-dimethylformamide and the following compound

[Chemical 15] 2.39 gr of a phosphonate represented by
so

[Chemical 17] 0.79 gr represented by

[Chemical formula 22] With mixing and stirring 1.04 gr of the aldehyde represented by
2.32 gr of a methanol solution of sodium methylate (28% by weight) was added dropwise at a temperature of about 5 ° C over about 8 minutes. The reaction product gradually precipitated. After further reacting at room temperature for 4 hours, the reaction solution was poured into about 400 ml of water.
The produced yellow precipitate was collected by filtration, washed with water and dried to obtain a crude product. The crude product was poured into about 100 ml of ethyl acetate, stirred at reflux temperature for about 5 minutes, and the mother liquor obtained by filtration was concentrated, redissolved in toluene and purified by column chromatography (silica gel / toluene). Further, recrystallization from toluene was performed twice to give yellow crystals (0.19, yield 8
%) Was obtained. Melting point: 300 ° C. Infrared absorption spectrum (KBr tablet method) 2230 cm ⁻¹ ; belong to νC≡N 1330 cm ⁻¹ ; belong to νC-F 980 cm ⁻¹ ; belong to δCH = CH (trans)

[Table 8] From the above results, the compound No. It was confirmed that 37 was obtained.

[Chemical formula 23]

Application Example An anode made of indium tin oxide (ITO) having a size of 3 mm × 3 mm and a thickness of 700 Å is formed on a glass substrate, and a hole transport layer 500 Å composed of a diamine derivative represented by the following formula 24 is formed thereon. Compound No. An electron transport layer 500Å composed of 3 and a cathode composed of aluminum were respectively formed by vacuum vapor deposition to produce an electroluminescent device. The degree of vacuum during vapor deposition is approximately 0.7 × 10 ⁻⁶ torr, and the substrate temperature is room temperature. When a direct current power supply was connected to the anode and cathode of the element thus manufactured through a lead wire, the applied voltage was 22 V at a current density of 100 mA / cm ² ,
A clear yellow-green emission was confirmed over a long period of time. At this time, the emission wavelength is 577 nm and the brightness is 190 cd / m.
^{Was 2} .

[Chemical formula 24]

[0030]

The asymmetry 9 represented by the above chemical formula 1 of the present invention
The -cyanostyryl-10-styrylanthracene derivative is novel and is extremely useful as a high-brightness organic electroluminescent device. Then, the asymmetric 9-cyanostyryl-10-styrylanthracene derivative is produced by the novel production method of the present invention.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yota Sakon 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Co., Ltd.

Claims (5)

[Claims] 1. The following chemical formula 1 An asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by: 2. The following chemical formula 2 The 9-cyanostyrylanthracene represented by A compound represented by the following formula is obtained, and then Characterized by reacting with a compound represented by: A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by: 3. The following chemical formula 5 The compound represented by the following formula: embedded image R ¹ —CHO (wherein R ^{1 is a} substituted or unsubstituted carbocyclic aromatic ring,
And a substituted or unsubstituted heterocyclic aromatic ring. ), And then reacting with an aldehyde compound shown below. Reacting with an aldehyde compound represented by the following formula, or reacting with an aldehyde represented by the above chemical formula 7, and then reacting with an aldehyde represented by the above chemical formula 6. A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by: 4. The following chemical formula 9 The 9,10-anthracene dialdehyde represented by
The following chemical formula 4 By reacting with a compound represented by By reacting with a compound represented by the above formula or by reacting with a compound represented by the above formula
Characterized by reacting with a compound represented by: A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by: 5. The following chemical formula 5 The compound represented by the following formula: embedded image R ¹ —CHO (wherein R ^{1 is a} substituted or unsubstituted carbocyclic aromatic ring,
And a substituted or unsubstituted heterocyclic aromatic ring. ) And an aldehyde compound represented by the following formula: Which is characterized by reacting with an aldehyde compound represented by A method for producing an asymmetric 9-cyanostyryl-10-styrylanthracene derivative represented by: