KR20150060183A - Bisisobenzofurandionylantracene compound, preparation method thereof and organic insulationg layer using the same - Google Patents

Abstract

The present invention relates to a bis-isobenzofuran-dionyl antracene compound, a manufacturing method thereof and an organic insulation film using the same wherein the bis-isobenzofuran-dionyl antracene compound can be used for manufacturing an organic insulator with high heat resistance. According to the present invention, a manufacturing method of the bis-isobenzofuran-dionyl antracene compound uses suzuki-coupling, which has few limitations for functional groups and high selectivity for reaction and accordingly has few side reactions, dehydration cyclization reaction and hydrolysis under base or acid conditions, thereby manufacturing bis-isobenzofuran-dionyl antracene with improved purity and yield.

Description

TECHNICAL FIELD The present invention relates to bisisobenzofurandionylantracene compound, preparation method thereof and organic insulation layer using the same,

The present invention relates to a bisisobenzofuran dionyl anthracene compound, a method for producing the same, and an organic insulating film using the same.

Conventionally, anthracene has been used for various purposes such as epoxy resin, carbon black production raw material, anthraquinone dye synthesis raw material and the like in addition to wood insecticides, preservation stabilizers and paints. Further, since anthracene is a condensed polycyclic aromatic compound condensed with three benzene rings, in addition to features such as structural hardness, height of carbon density, high melting point, and high refractive index, π electrons act due to ultraviolet irradiation, (Patent Document 1). Various applications of anthracene have been tested to further utilize these properties as added value. Until now, various anthracene derivatives have been developed as high-value-added materials in various fields of technology.

For example, a photo-curable polymer (Patent Document 2) serving as a sensitizer for photodynamic polymerization by introducing a (meth) acrylate group at positions 9 and 10 of anthracene to form a polymerizable monomer (Patent Document 2) (Patent Document 3) can be produced.

Also in the field of photoresist, a radiation-sensitive resin composition (Patent Document 4) which uses anthracene and has advantages such as high sensitivity, high resolution, high etching resistance and low solubility (Patent Document 4) Antireflection film and the like can be obtained (Patent Document 5).

Further, applications of anthracene as an electron transporting material or a light emitting material for an organic photoconductor (OPC), an organic electroluminescence device, an organic solar cell, an organic light emitting diode, and the like are expected (Patent Document 6).

Taking advantage of the fact that anthracene has a high refractive index, an anthracene has also been used as a hologram recording material in which, besides its use as an optical material, a high refractive index material, a low refractive index material, a sensitizing dye or the like are mixed and interference stripes are recorded by exposure (Patent Document 7).

As described above, the anthracene-based compound is remarkably attracting attention because it has versatility that enables reactions to be applied over various fields in a wide variety of reactions. Therefore, development of a compound having a novel anthracene skeleton capable of making a material highly functional and imparting new characteristics has been actively developed.

However, the conventional process for producing bisisobenzofuran dianiline anthracene has a disadvantage in that it is difficult to produce various derivatives due to a large number of functional groups, and the yield is low, resulting in a decrease in productivity and an increase in the disposal cost of wastes.

Therefore, the present inventors have found that a bisisobenzofuran dionyl anthracene compound which is useful for the production of a high heat-resistant organic insulator has fewer restrictions on functional groups and has high selectivity for the reaction, so that a Suzuki coupling having a low side reaction such as homo- Or a hydrolysis and dehydration cyclization reaction in an acidic condition, thereby improving the purity and yield.

Korean Patent Publication No. 2012-0086320 Japanese Patent Application Laid-Open No. 2007-99637 Japanese Patent Application Laid-Open No. 2008-1637 Japanese Patent Application Laid-Open No. 2005-346024 Japanese Patent Application Laid-Open No. 7-82221 Japanese Patent Application Laid-Open No. 2009-40765

It is an object of the present invention to provide a bisisobenzofuran dionyl anthracene compound.

Another object of the present invention is to provide a process for preparing the bisisobenzofuran diionyl anthracene compound.

It is still another object of the present invention to provide an organic insulating film for electronic devices derived from the bisisobenzofuran dionyl anthracene compound.

In order to achieve the above object,

There is provided a bisisobenzofuran dionyl anthracene compound represented by the following formula 1:

[Chemical Formula 1]

In Formula 1,

R ¹ , R ² , R ³ And R ⁴ are independently hydrogen, linear or branched C _{1 - 6} alkyl or C _{1 - 6} trialkylsilyl, and;

R ⁵ is -F or -CF _3, and; And

n is an integer of 0 to 3;

The present invention also relates to a process for producing a compound represented by the formula (1)

Suzuki coupling reaction of the compound represented by the formula (2) with the compound represented by the formula (3) under base and catalytic conditions to prepare the compound represented by the formula (4) (step 1);

Hydrolyzing the compound represented by the formula (4) prepared in the step (1) under a base condition to prepare a compound represented by the formula (5) (step 2); And

A step of dehydrating-ring-forming a compound represented by the formula (5) prepared in the step 2 under an acid condition to prepare a compound represented by the formula (1) (step 3); and a step of preparing the bisisobenzofuran diionyl anthracene compound The method provides:

[Reaction Scheme 1]

In the above Reaction Scheme 1,

R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n is as defined in Formula 1 above;

R ⁶ is a straight or branched C _{1 - 4} alkyl and;

X is halogen; And

Y is -B (OR ⁷ ) (OR ⁸ ), wherein R ⁷ And R ⁸ is Independently represent hydrogen or straight-chain or a C ₁ side chain _- which they are attached may form a 5 or 6-membered ring containing a boron atom with the _6-alkyl, or an oxygen atom bonded to which they are attached, where the carbon atoms present in the ring are each 1, or 2 linear or branched C _{1 - 6} alkyl which may be substituted with.

Further, the present invention provides an organic insulating film for an electronic device derived from the compound represented by the formula (1).

The bisisobenzofuran dionyl anthracene compound according to the present invention can be usefully used for the production of a high heat resistance organic insulator, and the process for producing the bisisobenzofuran diionyl anthracene compound according to the present invention has few restrictions on functional groups, Suzuki coupling having high selectivity due to low side reaction such as homo coupling and hydrolysis and dehydration cyclization reaction under basic or acid conditions are used, so that bisisobenzofuran diionylanthracene having improved purity and yield can be produced.

Hereinafter, the present invention will be described in detail.

The present invention provides a bisisobenzofuran dionyl anthracene compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ , R ² , R ³ And R ⁴ are independently hydrogen, linear or branched C _{1 - 6} alkyl or C _{1 - 6} trialkylsilyl, and;

R ⁵ is -F or -CF _3, and; And

n is an integer of 0 to 3;

Preferably, in the above formula (1)

R ¹ , R ² , R ³ And R ⁴ are independently hydrogen, linear or branched C _{1 - 4} alkyl and;

R ⁵ is -F or -CF _3, and; And

and n is a bisisobenzofuran dionyl anthracene compound having an integer of 0 to 1.

More preferably, the bisisobenzofuran dionyl anthracene compound represented by the above formula (1) is a 9,10-bis [4- (isobenzofuran-1,3-dioyl)] - 2,6- Butyl) anthracene.

The present invention also relates to a process for producing a compound represented by the formula (1)

Suzuki coupling reaction of the compound represented by the formula (2) with the compound represented by the formula (3) under base and catalytic conditions to prepare the compound represented by the formula (4) (step 1);

Hydrolyzing the compound represented by the formula (4) prepared in the step (1) under a base condition to prepare a compound represented by the formula (5) (step 2); And

A step of dehydrating-ring-forming a compound represented by the formula (5) prepared in the step 2 under an acid condition to prepare a compound represented by the formula (1) (step 3); and a step of preparing the bisisobenzofuran diionyl anthracene compound ≪ / RTI >

[Reaction Scheme 1]

In the above Reaction Scheme 1,

R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n is as defined in Formula 1 above;

R ⁶ is a straight or branched C _{1 - 4} alkyl and;

X is halogen; And

Y is -B (OR ⁷ ) (OR ⁸ ), wherein R ⁷ And R ⁸ is Independently represent hydrogen or straight-chain or a C ₁ side chain _- which they are attached may form a 5 or 6-membered ring containing a boron atom with the _6-alkyl, or an oxygen atom bonded to which they are attached, where the carbon atoms present in the ring are each 1, or 2 linear or branched C _{1 - 6} alkyl which may be substituted with.

Preferably, in Scheme 1,

R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n is as defined in Formula 1 above;

R ⁶ is a straight or branched C _{1 -} and _2-alkyl;

X is bromine, chlorine or iodine; And

,

,

,

및

으로 이루어진 군으로부터 선택되는 1종이다.
Y is

,

,

,

And

≪ / RTI >

Hereinafter, the above manufacturing method will be described in detail for each step.

First, in the production process according to the present invention, step 1 is a step of Suzuki coupling reaction of the compound represented by formula (2) with the compound represented by formula (3) under base and catalytic conditions to prepare the compound represented by formula (4).

Specifically, the step 1 is a step of coupling a phenyl group substituted with a dialkylcarbonyl group as a precursor thereof to substitute an isobenzofuranedioyl group for an anthracene group of the compound represented by the formula (2) to obtain a bis-dialkyl To prepare a carbonylphenyl anthracene compound.

In the step 1, the catalyst may be any catalyst as long as it is a catalyst commonly used in Suzuki coupling. However, it is preferable to use a catalyst such as tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, (Tri-o-tolylphosphine) palladium dichloride, bis (dibenzylideneacetone) palladium, bis (tricyclohexylphosphine) palladium dichloride, bis (1,2-bis (diphenylphosphino) ethane] palladium dichloride, and the like are used as the initiator in the case of using 1,2-bis (triphenylphosphine) palladium diacetate, It is most preferred to use tetrakis (triphenylphosphine) palladium.

In the step 1, the base may be any catalyst as long as it is a catalyst commonly used in Suzuki coupling, but it is preferable to use cesium carbonate, sodium carbonate, potassium carbonate, potassium hydroxide, sodium hydroxide, barium hydroxide, It is more preferable to use cesium carbonate or potassium carbonate.

Further, in the above step 1, the solvent may be any catalyst that is commonly used in Suzuki coupling without limitation, but may be 1,4-dioxane, dimethyl ether, dimethylformamide, ethanol, methanol, dimethylsulfoxide, Propanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-butanol, 2-propanol, 2- Butanol, acetone, 2-butanone, 3-methyl-2-butanone, 2-pentanone, 3-pentanone, Dimethyl-3-pentanone, dioxolane, N-methylpyrrolidone, diethoxyethane, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol ethyl methyl ether, diethylene glycol, diethylene glycol Monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol di Ether, diethylene glycol methyl ether, may be used alone or in combination, such as ethylbenzene, anisole, nitrobenzene, tetramethylurea.

In the step 1, the reaction temperature is preferably 10 ° C to 150 ° C, more preferably 20 ° C to a boiling point of the solvent, and the reaction time is preferably 30 minutes to 24 hours, more preferably 1 to 12 hours More preferable.

Next, in the production method according to the present invention, Step 2 is a step of hydrolyzing the compound represented by Chemical Formula 4 prepared in Step 1 under basic conditions to prepare the compound represented by Chemical Formula 5. [

Specifically, the step 2 is a step of hydrolyzing the bis-dialkylcarbonylphenyracene compound represented by the formula (4) prepared in the step 1 under basic conditions to obtain bis-dihydroxycarbonylphenylanthracene represented by the formula .

In the step 2, the base can be used without limitation as long as it is a base commonly used in the hydrolysis reaction, but bases such as potassium hydroxide, sodium hydroxide, barium hydroxide and calcium hydroxide are preferably used, desirable.

In the step 2, the solvent may be any solvent conventionally used in the hydrolysis reaction, but it is not limited to ethanol, methanol, 1-propanol, 2-propanol, 2-methyl- 2-propanol, 1-butanol, 2-butanol, etc. may be used alone or in combination, but methanol or ethanol alone is more preferably used.

Further, in the step 2, the reaction temperature is preferably 10 ° C to 150 ° C, more preferably 20 ° C to a boiling point of the solvent, and the reaction time is preferably 30 minutes to 24 hours, more preferably 1 to 20 hours More preferable.

Next, in the production process according to the present invention, step 3 is a step of dehydrating-ring-forming a compound represented by the formula (5) prepared in the step 2 under an acid condition to prepare a compound represented by the formula (1).

Specifically, the step 3 is a step in which the bis-dihydroxycarbonylphenylanthracene represented by the formula (5) prepared in the step 2 is dehydrated and cyclized under an acid condition to obtain bisisobenzofuran dionyl anthracene ≪ / RTI > compound.

In the step 3, the acid can be used without limitation as long as it is an acid conventionally used in the dehydration cyclization reaction, but acetic anhydride, hydrochloric acid, sulfuric acid, nitric acid and the like are preferably used, and acetic anhydride is more preferably used.

In the step 3, the solvent may be selected from toluene, xylene, benzene, tetrahydrofuran, dioxane, dichloromethane, 1,2-dimethoxyethane, dichloromethane, dichloroethane and chloroform have.

Further, in the step 3, the reaction temperature is preferably 10 ° C to 150 ° C, more preferably 20 ° C to a boiling point of the solvent, and the reaction time is preferably 30 minutes to 24 hours, more preferably 1 to 10 hours More preferable.

As described above, the process for producing the bisisobenzofuran dionyl anthracene compound according to the present invention is characterized in that there are few restrictions on the functional groups and the selectivity of the reaction is high, so that the Suzuki coupling with few side reactions such as homo coupling and the Hydrolysis and dehydration cyclization are used, bisisobenzofuran dionyl anthracene having improved purity and yield can be produced.

Further, the present invention provides an organic insulating film for electronic devices derived from a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n are the same as defined above.

Hereinafter, the present invention will be described in detail with reference to examples.

However, the following examples are illustrative of the present invention, and the contents of the present invention are not limited to the following examples and experimental examples.

< Production Example 1 > 9,10- Bis (4,4,5,5- Tetramethyl - [1,3,2] - Dioxaborolane Yl) -2,6-di ( tert -Butyl) anthracene &lt; / RTI &gt;

Step 1: 2,6- D( tert -Butyl) anthracene  Produce

Anthracene (50 g, 0.28 mmol) was dispersed in trifluoroacetic acid (TFA, 350 mL) and t-butanol (t-BuOH, 80 mL, 0.84 mol) was added and the mixture was refluxed for 18 hours. After completion of the reaction of the reaction mixture, the reaction mixture was cooled to room temperature and organic matters were separated by filtration. The organic material was dissolved in dichloromethane (400 mL), and the residual acid was washed and neutralized with water and a 20% aqueous solution of sodium hydrogencarbonate (NaHCO ₃ ), respectively, and the organic layer was separated. The residue was dried over magnesium sulfate (MgSO ₄ ), and the organic layer was concentrated, dispersed in hexane (400 mL), filtered and dried to give 2,6-di ( tert -butyl) anthracene (64.6 g, 80%).

¹ H NMR (500 MHz, DMSO-D ₆ )? (Ppm) 8.32 (2 H, d), 7.90 (2 H, d), 7.86 H, s)

Step 2: 9,10- Dibromo -2,6- Of di (tert-butyl) anthracene  Produce

2,6-di ( tert -butyl) anthracene (32 g, 0.1 mmol) prepared in Step 1 was dissolved in dichloromethane (335 mL) and cooled to 0 ° C. Br ₂ , 12.6 mL, 0.25 mol) was slowly added dropwise and the mixture was stirred at room temperature for 16 hours. 10% aqueous sodium hydrogencarbonate (170 g) was added dropwise and stirred for 30 minutes to deactivate the residual bromine. The organic layer was separated from the reaction mixture, and the residual acid was washed and neutralized with water and a 10% aqueous solution of sodium hydrogencarbonate. The residue was dried with magnesium sulfate (MgSO ₄ ), concentrated, and recrystallized with toluene to obtain 9,10-dibromo-2,6-di (tert-butyl) anthracene (40.1 g, 80%).

¹ H NMR (500 MHz, CDCl ₃ )? (Ppm) 8.54 (2 H, d), 8.48 (2 H, d), 7.74

Step 3: 9,10-Bis (4,4,5,5-tetramethyl- [1,3,2] -dioxabororane-2- yl) -2,6-di tert -Butyl) anthracene &lt; / RTI &gt;

9,10-dibromo-2,6-di (tert-butyl) anthracene (25 g, 56 mmol) prepared in the above step 2 was dissolved in 1,4-dioxane (500 mL) Bis (diphenylphosphino) ferrocene] dichloride (PdCl ₂ (dppf), 4.6 g) was added to a solution of bis (pinacolato) diboron (56 g, 223 mmol), potassium acetate (66 g) Was added and the mixture was heated and stirred for 24 hours. The reaction mixture was cooled to room temperature, and then poured into about 300 mL of water to terminate the reaction. The organic material was extracted with dichloromethane, dried over magnesium sulfate (MgSO ₄ ), concentrated and then subjected to column purification to obtain 9,10-bis (4,4,5,5-tetramethyl- [1,3,2] Yl) -2,6-di (tert-butyl) anthracene (21.3 g, 70%).

¹ H NMR (300 MHz, CDCl ₃ )? (Ppm) 8.29 (2 H, d), 8.24 (2 H, d), 7.57 , s)

< Manufacturing example  2> Diethyl -4- Iodophthalate  Produce

Step 1: 4- Iodophthalic acid  Produce

Iodoxylene (31 mL, 0.22 mol) was dissolved in pyridine (125 mL) and water (375 mL). Potassium permanganate (205 g, 1.3 mol) was slowly added at 60 ° C and stirred for 16 hours. After completion of the reaction of the reaction mixture, the solid impurities were removed by passing through Celite while maintaining the temperature at 60 ° C. The filtrate was cooled to room temperature, acidified (pH = 2) with 6 N hydrochloric acid, extracted with ethyl acetate, concentrated and then subjected to column purification to obtain 4-iodophthalic acid (44 g, 69%).

¹ H NMR (500 MHz, DMSO-D ₆ )? (Ppm) 13.44 (1H, d), 7.98

Step 2: Diethyl -4- Iodophthalate  Produce

4-iodophthalate (37.5 g, 0.13 mmol) prepared in the above step 1 was dissolved in ethanol (120 mL), and concentrated sulfuric acid (3 mL) was added. The mixture was heated to reflux for 6 hours, cooled to room temperature , And extracted with ethyl acetate. Washed with a diluted aqueous potassium hydroxide solution and water, dried over magnesium sulfate, concentrated and then subjected to column purification to obtain diethyl-4-iodophthalate (32.9 g, 74%).

¹ H NMR (500 MHz, DMSO-D ₆ )? (Ppm): 8.04 (1H, d), 8.03 (1H, dd), 7.51 (6 H, t)

< Example  1> 9,10-Bis [4- ( Isobenzofuran -1,3- Dionyl )] - 2,6- Of di (tert-butyl) anthracene  Produce

Step 1: 9,10-Bis [(3,4- Diethoxycarbonyl ) Phenyl ] -2,6- Of di (tert-butyl) anthracene  Produce

(4,4,5,5-tetramethyl- [1,3,2] -dioxabororane-2-yl) -2,6-di (tert- (16.7 g, 47.9 mmol) prepared in Preparation Example 2 and tricyclo [2.2. 2] octane were dissolved in 1,4-dioxane (200 mL) (15 g, 46.1 mmol) and hexylphosphine (PCy ₃ , 370 mg), tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ , 500 mg) and Cs ₂ CO ₃ And reacted at a temperature of 80 캜 for 24 hours. After the reaction was cooled to room temperature, the reaction was poured into about 300 mL of water and the reaction was terminated. The organic layer was extracted with dichloromethane, and then the aqueous layer and the organic layer were separated using dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, and concentrated by column purification to give 9,10-bis [(3,4-diethoxycarbonyl) phenyl] -2,6-di (tert- butyl) anthracene as yellow solid 1.7 g, 63%).

¹ H NMR (300 MHz, CDCl ₃ )? (Ppm) 8.03 (2H, d), 7.87 (2H, d), 7.70 , d), 7.49 (2H, dd), 4.53 (4H, dd), 4.44 (4H, dd), 1.50 )

Step 2: 9,10-Bis [(3,4- Dihydroxycarbonyl ) Phenyl ] -2,6-di ( tert -Butyl) anthracene &lt; / RTI &gt;

2,2-di (tert-butyl) anthracene (2 g, 2.7 mmol) prepared in the above step 1 was dissolved in ethanol (28 mL) After dispersion, 20% potassium hydroxide (40 g) was added and the mixture was refluxed for 16 hours. After the reaction was completed, the reaction was cooled to room temperature, acidified (pH = 2) with 6N hydrochloric acid, and the precipitated crystals were filtered, washed with water and dried to obtain 9,10-bis [(3,4-dihydroxycarbo Phenyl) -2,6-di (tert-butyl) anthracene as a yellow solid (1.6 g, 98%).

¹ H NMR (300 MHz, DMSO- ₆ ) 隆 (ppm) 13.91 (3 H, s), 8.04 (2 H, d), 7.75 H, d), 7.55 (2 H, d), 7.43 (2 H, s), 1.29 (18 H, s)

Step 3: 9,10-Bis [4- ( Isobenzofuran -1,3- Dionyl )] - 2,6- Of di (tert-butyl) anthracene  Produce

2,6-di (tert-butyl) anthracene (1.7 g, 2.8 mmol) prepared in Step 2 was dissolved in toluene (14 mL) And acetic anhydride (13.6 mL) was added. The mixture was stirred and refluxed for 6 hours, then cooled and filtered. The residue was washed with dichloromethane and dried to give 9.10-bis [4- (isobenzofuran-1,3-dioyl)] - 2,6-di (tert- butyl) anthracene as a yellow solid , 95%).

¹ H NMR (500 MHz, DMSO-D ₆ )? (Ppm) 7.70 (2 H, d), 7.69 (2 H, dd), 7.52 18 H, s)

Claims (10)

A bisisobenzofuran dionyl anthracene compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
R ¹ , R ² , R ³ And R ⁴ are independently hydrogen, linear or branched C _{1 - 6} alkyl or C _{1 - 6} trialkylsilyl, and;
R ⁵ is -F or -CF _3, and; And
and n is an integer of 0 to 3).
The method according to claim 1,
In Formula 1, R ¹ , R ² , R ³ And R &lt; ⁴ &gt; are independently hydrogen, straight or branched C _1-4 alkyl;
R ⁵ is -F or -CF _3, and; And
and n is an integer of 0 to 1. &lt; Desc / Clms Page number 24 &gt;
The method according to claim 1,
The bisisobenzofuran dionyl anthracene compound represented by the formula (1) is a 9,10-bis [4- (isobenzofuran-1,3-dioyl)] -2,6-di (tert- Wherein the bisisobenzofuran dionyl anthracene compound is a bisisobenzofuran dionyl anthracene compound.
As shown in Scheme 1 below,
Suzuki coupling reaction of the compound represented by the formula (2) with the compound represented by the formula (3) under base and catalytic conditions to prepare the compound represented by the formula (4) (step 1);
Hydrolyzing the compound represented by the formula (4) prepared in the step (1) under a base condition to prepare a compound represented by the formula (5) (step 2); And
A process for producing a bis (isobenzofurandionyl) anthracene compound according to claim 1, comprising the step of dehydrating-ring-forming a compound represented by the general formula (5) prepared in the step (2) : &Lt;
[Reaction Scheme 1]

(In the above Reaction Scheme 1,
R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n are the same as defined in the above formula (1);
R ⁶ is a straight or branched C _{1 - 4} alkyl and;
X is halogen; And
Y is -B (OR ⁷ ) (OR ⁸ ), wherein R ⁷ And R ⁸ is Independently represent hydrogen or straight-chain or a C ₁ side chain _- which they are attached may form a 5 or 6-membered ring containing a boron atom with the _6-alkyl, or an oxygen atom bonded to which they are attached, where the carbon atoms present in the ring are each 1, or 2 linear or branched C _{1 - 6} alkyl may be substituted with a).
5. The method according to claim 4,
R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n are the same as defined in the above formula (1);
R ⁶ is a straight or branched C _{1 -} and _2-alkyl;
X is bromine, chlorine or iodine; And
Y is

,

,

,

And

Wherein the bisisobenzofuran dionyl anthracene compound is at least one selected from the group consisting of:
5. The method of claim 4,
The catalyst of step 1 is preferably selected from the group consisting of tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, palladium acetate, palladium chloride, palladium black, bis (triphenylphosphine) palladium dichloride, bis bis (tricyclohexylphosphine) palladium dichloride, bis (triphenylphosphine) palladium diacetate, [1,2-bis (diphenylphosphine) palladium (Phenylphosphino)) butane] palladium dichloride and [1,2-bis (diphenylphosphino) ethane] palladium dichloride. The bisisobenzofuran dionyl anthracene compound is at least one compound selected from the group consisting of Way.
5. The method of claim 4,
Wherein the base of step 1 is at least one selected from the group consisting of cesium carbonate, potassium acetate, sodium carbonate, potassium carbonate, potassium hydroxide, sodium hydroxide and barium hydroxide.
5. The method of claim 4,
Wherein the base of step 2 is at least one base selected from the group consisting of potassium hydroxide, sodium hydroxide, barium hydroxide and calcium hydroxide.
5. The method of claim 4,
Wherein the acid of step 3 is at least one selected from the group consisting of acetic anhydride, hydrochloric acid, sulfuric acid and nitric acid.
An organic insulating film for electronic devices derived from a compound represented by the following formula (1)
[Chemical Formula 1]

.
(In the above Reaction Scheme 1,
R ¹ , R ² , R ³ , R ⁴ , R ⁵ And n are the same as defined in the above formula (1).